 Novel compound having effect of promoting neuron differentiation
专利摘要:
Provided is a novel cystacycline derivative having excellent neuronal differentiation promoting action and useful for the treatment of central nervous system disorders and peripheral nervous system disorders. 公开号:KR20010022204A 申请号:KR1020007000776 申请日:1998-07-24 公开日:2001-03-15 发明作者:사이토세이이치；나가이마사시；모리노도미오；도미요시쓰기오；니시기오리다카아키；구와하라아쓰시；사토다카미치；하라다다카시 申请人:닛뽄카야쿠가부시키가이샤； IPC主号:
专利说明:
NOVEL COMPOUND HAVING EFFECT OF PROMOTING NEURON DIFFERENTIATION Neurotrophic factors are protein compounds that are involved in inducing differentiation of neurons and maintaining their identity and survival. Neuronal growth factors (hereinafter referred to simply as "NGF") are known as representative of these compounds [Ann. Neuro., 10, 499-503 (1981). This indicates that NGF is deeply involved in the differentiation, survival and recovery of neurons in the central and peripheral nervous systems. When nerves are damaged by aging, internal and external factors, pathological symptoms develop. These injuries cause dementia, Alzheimer's disease, cerebral injury from cerebral vascular injury, muscle stiffness caused by Parkinson's disease, tremor in the central nervous system. In addition, damage in the peripheral nervous system is caused by motor dysfunction due to nerve cell damage due to accidents, amyotrophic lateral sclerosis, spinal muscular atrophy, neuropathy, diabetes mellitus, uremia, vitamin B1 or B12 deficiency, chronic liver disease, Carcinosarcoma, hereditary dysplasia, hypothyroidism, cancer, vasculitis, Sjogren's syndrome, immunological diseases following infection, hereditary diseases, physical pressure, drugs (anticancer drugs, Mycobacterium tuberculosis inhibitors, antiepileptics, etc.) or poisoning (arsenic) , Thallium, carbon disulfide, etc.) (for more details, see RINSHO KENSA (Clinical Test), 40, 760-766 (1996)). Conventionally, when neurons are irreversibly damaged from these disorders, it has been recognized that regeneration and repair of damaged neurons are difficult. However, on the assumption that various neuropathy factors act on neurons, they can treat neuropathy. Therefore, neuropathy factors have been developed as various drugs for neuropathy [Science, 264, 772-774 (1994)]. Clinical trials of NGF are underway for Alzheimer's disease, nerve damage, or spinal cord injury. NGF is a series of proteins with a molecular weight of about 50,000. Treatment of neuropathy usually takes a long time. For these reasons, it is difficult to develop a pharmaceutical that can be efficiently administered. Gene therapy, or induction of the NGF gene, is another option for treatment but its therapeutic effect is still unknown. When NGF is present, PC 12 cells, which are cloned cell lines cloned from the adrenal medulla chromophiloma of rats, terminate and differentiate cell proliferation into neuronal cells with neuronal processes. By this process, it is possible to screen for an active substance having an NGF-like neuronal differentiation promoting effect. For example, the antibiotic stostrosporin was found to have a P12 cell differentiation promoting effect [SHINKEI KAGAKU, 26, 200-220 (1987)]. Similar differentiation promoting action, Streptomyces sp. Recently, the bioactive compound NK175203 (hereinafter referred to as cystacyclin) produced from the NK175203 strain FERM BP-4372 (WO 95/31992) was also observed. However, its application as a medicament is difficult due to its toxicity and pharmacokinetics in vivo. Therefore, there is a strong demand for the development of low molecular weight compounds that exhibit neuronal cell differentiation promoting action and are low toxic and easy to manufacture. The present invention relates to a novel compound having a neuronal differentiation promoting action and a pharmaceutical use thereof. 1 is an infrared absorption spectrum of NA32176A (compound of formula [1E]) measured using a potassium bromide tablet. 2 is a hydrogen nuclear magnetic resonance spectrum of NA32176A (compound of general formula [1E]) measured in heavy water. 3 is a hydrogen nuclear magnetic resonance spectrum of NA32176A (compound of general formula [1E]) measured in heavy water. Best Mode for Implementation of the Invention Compounds of the present invention represented by the general formulas [1A], [1B], [1C], [1D], [1E], and [1F] exhibit a function of promoting cell differentiation, thus preventing the treatment of neuropathy in the central and peripheral nervous systems. Can be used as a medicine for The compounds of the present invention are described in more detail below. [A] Compounds of General Formula [1A] In General Formula [1A], X A is 0, S or SO, most preferably S. In the general formula [1A], a linear or branched aliphatic group having 1 to 20 carbon atoms represented by Y A is an alkyl group or alkenyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 6 carbon atoms, such as Methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, isopropyl group or tert-butyl group, more preferably a linear aliphatic group having 1 to 4 carbon atoms, Most preferably, it is an ethyl group. The aliphatic group may be unsubstituted or may be substituted. When an aliphatic group is substituted, 1-6 substituents, Preferably 1-3 may exist in an aliphatic group. Examples of these substituents include carboxyl groups or groups derived therefrom, amino groups or groups derived therefrom, or hydroxy groups or groups derived therefrom. In the monocyclic aromatic heterocyclic ring and aromatic hydrocarbon having 3 to 6 carbon atoms in the general formula [1A], the aromatic hydrocarbon group is preferably a benzene ring, and a monocyclic aromatic heterocyclic ring contains a nitrogen atom, an oxygen atom or a sulfur atom. 5 or 6 membered ring means. Examples of the substituent in the case where these substituents are substituted are the same as those in the aliphatic group. Examples of the group derived from a carboxy group include carboxyl functional groups such as esterified or amidated carboxyl groups, cyano groups, hydroxymethyl groups or aminomethyl groups formed by reduction of these substituents, and derivatives derived from them by acylation of these functional groups. It includes a functional group. Preferably, the carboxyl group or group derived therefrom includes a carboxyl group, COOR1 (where R1 is an unsubstituted or substituted alkyl, alkenyl, or alkynyl group having 1 to 4 carbon atoms) and COW (where W is an unsubstituted or substituted saturation). Heterocyclic). The alkyl group, alkenyl group or alkynyl group represented by R 1 in COOR 1 may be linear, branched or cyclic. When R1 is substituted, 1 to 6 substituents, preferably 1 to 3, may be present in R1, and examples of the substituent include halogen, hydroxy group, carboxyl group, methoxycarbonyl group, cyano group and acetylamino group. R 1 is preferably unsubstituted. Examples of the alkyl group include methyl group, ethyl group, ethylene group, n-propyl group, isopropyl group, cyclopropyl group, n-butyl group, isobutyl group, tert-butyl group and cyclobutyl group, and preferably methyl group, ethyl group and ethylene Group, n-propyl group, More preferably, it is a methyl group. Examples of the alkenyl group include a vinyl group, 2-propenyl group, isopropenyl group and 2-butenyl group. Representative examples of alkynyl groups are 2-propenyl. W represents a heterocyclic ring, preferably a saturated heterocyclic ring, more preferably a ring such as azetidine, piperidine, pyrrolidine, morpholine or piperazine. These heterocycles may be bonded to a carbonyl group via a carbon or nitrogen atom, and are preferably bonded to a carbonyl group via nitrogen. When a hetero ring is substituted, 1-4 substitutions, Preferably 1-2 may exist in each ring. Preferred examples of these substituents are carboxyl groups or groups derived therefrom, more preferably carboxyl groups and COOR11, wherein R11 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms; in this case the alkyl group and this alkyl group are substituted And the substituents are the same as those described above for R1.). Examples of groups derived from an amino group include heterocycles containing a nitrogen group of a functional group, a nitro group, a hydroxylamino group, an imino group, and an amino group which alkylate, acylate or sulfonate the amino group, preferably NR2R3 (where R2 and R3 may be the same as or different from each other, and independently represent hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or an acyl group having 1 to 5 carbon atoms). In the group represented by NR2R3, the alkyl group in R2 and R3 and the substituents when this alkyl group is substituted are the same as in R1. The acyl group in R2 and R3 may be linear, branched, cyclic, saturated or unsaturated. When the acyl group is substituted, the substituent is the same as in R1. More preferably, the group derived from the amino group is represented by NHCOR12 (where R12 is an alkyl group having 1 to 4 carbon atoms, and the example of R12 is the same as in R1), and most preferably R12 is a methyl group. Examples of groups derived from hydroxy groups are functional groups which alkylate or acylate hydroxy groups, such as OCOR14, wherein the alkylated functional groups in R14 are unsubstituted or substituted alkyl groups, examples of which alkyl groups are the same as in R1, Acylated functional groups are unsubstituted or substituted acyl groups, examples of which are the same as in R2), ketos and halogens. Z1 A , Z2 A and Z3 A in the general formula [1A] are each a carboxyl group or a group derived therefrom, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, a hydroxy group or a group derived therefrom, an amino group or a derivative thereof To a derived group, a sulfate group or a group derived therefrom, a phosphate group or a group derived therefrom, a monocyclic aromatic heterocycle, halogen or hydrogen, or Z2 A and Z3 A are bonded together and substituted or unsubstituted To form an aromatic hydrocarbon or an aromatic heterocycle. In this case, Z 1 A is a carboxyl group or group derived therefrom, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, a hydroxy group or a group derived therefrom, an amino group or a group derived therefrom, halogen or hydrogen. Examples of groups derived from sulfates are groups derived from sulfonamide derivatives such as SO 2 NH 2 , SO 2 NHCH 3 , SO 2 N (CH 3 ) 2, and SO 2 NHCOCH 3 . Examples of groups derived from phosphate are P (O) (OH) H, P (O) (OH) (NH 2 ) and P (O) (OH) CH (OCH 3 ) 2 . Examples of groups derived from carboxyl groups, hydroxyl groups and amino groups are the same as described above. Examples of groups derived from amino groups further include NHSO 2 Ph, NHCOCF 3 , NHCOC 2 F 5 , NHSO 2 CF 3 and NHSO 2 C 2 F 5 . Preferred examples of Z1 A , Z2 A and Z3 A include carboxy, COOR4 (where R4 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), CONR5R6 (where R5 and R6 may be the same as or different from each other, and independently Hydrogen or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, cyano, hydroxy group, OR7 (where R7 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or an unsubstituted or substituted carbon atom having 1 to 5 carbon atoms NR8R9 (where R8 and R9 may be the same or different, respectively), independently hydrogen, unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or unsubstituted or substituted acyl group having 1 to 5 carbon atoms ), CH 2 OR10 (where R10 is hydrogen, unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or unsubstituted or substituted acyl group having 1 to 5 carbon atoms), 5-tetrazolyl, halogen or hydrogen do. The above-mentioned unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, the alkyl group represented by R4, R5, R6, R7, R8, R9 or R10 and each substituent when these groups are substituted are the same as in R1. The acyl group represented by R7, R8, R9 or R10 and each substituent when these groups are substituted are the same as in R2. Specific examples of the acyl group include acetyl group, propionyl group, acroyl group, propionyl group, n-butyryl group, isobutyryl group, crotonoyl group, valeryl group, isovaleryl group and pivaloyl group, and are preferable. Preferably they are an acetyl group, a propionyl group, an acroyl group, and a propionyl group, More preferably, they are an acetyl group. Particularly preferred combinations of R8 and R9 are those in which R8 is hydrogen and R9 is an acetyl group. Examples of halogens are fluorine, chlorine, bromine and iodine, with fluorine and chlorine being preferred. Preferred examples of the substituents on Z1 A , Z2 A and Z3 A are one or two substituents other than hydrogen, more preferably carboxyl group, COOR4, OCOR13 (where R13 is an alkyl group having 1 to 4 carbon atoms, and Examples of the alkyl group are the same as those for R1.), A hydroxy group and CH 2 OR10, most preferably a carboxyl group, methoxycarbonyl group, hydroxymethyl group, hydroxy group and acetyloxymethyl group. Examples of the aromatic hydrocarbon formed by bonding of Z2 A and Z3 A are a benzene ring and a naphthalene ring. Examples of aromatic heterocycles bonded by Z2 A and Z3 A are 6-membered heteroaryls such as pyridine, pyrazine or pyrimidine rings and thiophene, pyrrole, furan, oxazole, thiazole, isoxazole, isothiazole or azole 5-membered rings, such as a ring. Preferably, the group formed by Z2 A and Z3 A is an aromatic hydrocarbon, more preferably a benzene ring. Examples of substituents when the ring is substituted are the same as in the case of those of Z. Preferred examples of these substituents include an alkyl group having 1 to 4 carbon atoms, preferably a methyl group, ethyl group, n-propyl group and isopropyl group which may be unsubstituted or substituted with halogen (eg, fluorine) such as trifluoromethyl group; Alkyloxy groups having 1 to 4 carbon atoms such as a methoxy group and an ethoxy group; Nitro groups, and halogens such as fluorine, chlorine or bromine. Compound of general formula [1B] In the compound of the present invention represented by general formula [1B], X B is S, O or SO, most preferably S. The straight or branched aliphatic hydrocarbon group having 7 to 20 carbon atoms represented by Y B means an alkyl group or alkenyl group having 7 to 20 carbon atoms. Examples of the alkyl group or alkenyl group are n-pentyl group, n-octyl group, n-nonyl group, n-decanyl group, n-undecanyl group, n-dodecanyl group, n-tridecanyl group, n-tetradecanyl group , n-pentadecanyl group, n-dodecanyl group, n-hexadecanyl group, n-pentadecanyl group and n-octadecanyl group, preferably an alkyl group having 7 to 15 carbon atoms, most preferably n-dode It is a practical skill. The aliphatic hydrocarbon group may be unsubstituted or may be substituted. When an aliphatic hydrocarbon group is substituted, 1-6 substituents, Preferably 1-3 may exist in an aliphatic group. These substituents include a carboxyl group or a group derived therefrom, an amino group or a group derived therefrom, or a hydroxy group or a group derived therefrom. Examples of the group derived from a carboxy group include carboxyl functional groups such as esterified or amidated carboxyl groups, cyano groups, hydroxymethyl groups or aminomethyl groups formed by reduction of these substituents, and derivatives derived from them by acylation of these functional groups. It includes a functional group. Preferably, the carboxyl group or group derived therefrom includes a carboxyl group and COOR 6, wherein R 6 is an unsubstituted or substituted alkyl, alkenyl, or alkynyl group having 1 to 4 carbon atoms. The alkyl group, alkenyl group or alkynyl group represented by R 6 in COOR 6 may be linear, branched or cyclic. Examples of the substituent when R 6 is substituted include halogen, hydroxy group, carboxyl group, methoxycarbonyl group, cyano group and acetamido group. R 6 is preferably unsubstituted. Examples of the alkyl group include methyl group, ethyl group, ethylene group, n-propyl group, isopropyl group, cyclopropyl group, n-butyl group, isobutyl group, tert-butyl group and cyclobutyl group, and preferably methyl group, ethyl group and ethylene Group, n-propyl group. Examples of the alkenyl group include a vinyl group, 2-propenyl group, isopropenyl group and 2-butenyl group. Representative examples of alkynyl groups are 2-propenyl groups. Examples of groups derived from amino groups include heterocycles containing a nitrogen group of a functional group, nitro group, hydroxylamino group, imino group, and amino group which alkylate, acylate or sulfonate the amino group, preferably NR7R8 (where R7 and R8 may be the same as or different from each other, and independently represent hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or an acyl group having 1 to 5 carbon atoms). In the group represented by NR7R8, the alkyl group at R7 and R8 and the substituents when the alkyl group is substituted are the same as those at R6. The acyl group in R7 and R8 may be linear, branched, cyclic, saturated or unsaturated. The substituents when the acyl group is substituted are the same as in R6. Representative examples of the acyl group include acetyl group, propionyl group, acroyl group, propionyl group, n-butyryl group, isobutyryl group, crotonoyl group, valeryl group, isovaleryl group and pivaloyl group, preferably Is an acetyl group, propionyl group, acroyl group and propionyl group, More preferably, it is an acetyl group. Particularly preferred combinations of R 7 and R 8 are those in which R 7 is hydrogen and R 8 is an acetyl group. Examples of groups derived from hydroxy groups include functional groups that alkylate or acylate hydroxy groups, such as OCOR14, where the alkylated functional groups in R14 are unsubstituted or substituted alkyl groups, examples of which alkyl groups are the same as in R6; and The silylated functional groups are unsubstituted or substituted acyl groups, examples of which are acyl groups as in R7) and keto and halogen. In the compound of the general formula [1B], examples of the linear or branched aliphatic group having 1 to 6 carbon atoms substituted with COW include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group and n -Hexyl group, isopropyl group, and tert-butyl group are mentioned, Preferably it is a C1-C4 linear aliphatic group, More preferably, it is an ethyl group. In the aliphatic group, at least one hydrogen, preferably one hydrogen, must be replaced with COW. W represents an unsubstituted or substituted heteroaryl group or a saturated aromatic heterocycle, preferably a saturated aromatic heterocycle, more preferably an azetidine, piperidine, pyrrolidine, piperazine or morpholine ring. These heterocycles may be bonded to a carbonyl group via a carbon or nitrogen atom, preferably through a nitrogen atom. In the case where the heterocycle is substituted, each ring may have 1 to 4, preferably 1 to 2 substituents. Preferred examples of these substituents include a carboxyl group, a hydroxyalkyl group having 1 to 4 carbon atoms, a phenyl group or COOR9 (wherein R9 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms; in this case, the alkyl group and this alkyl group are substituted). The substituents are the same as in R6 above.). Examples of the hydroxyalkyl group are 2-hydroxyethyl group, 2-hydroxypropyl group, 3-hydroxypropyl group and 4-hydroxybutyl group, preferably 2-hydroxypropyl group. COOR9 is preferably a tert-butoxycarbonyl group. In COOR 9 one or more hydrogens, preferably one hydrogen, may be substituted with an amino group or a group derived therefrom. Examples of the group derived from an amino group are as described above, preferably NR10R11 (where R10 and R11 may be the same or different, respectively, independently hydrogen, an alkyl group having 1 to 4 carbon atoms or an acyl group having 1 to 5 carbon atoms). ). In the group represented by NR10R11, the alkyl group and the substituents in which the alkyl group is substituted are the same as those in R6 described above. In the group represented by NR10R11, the acyl group in R10 and R11 may be linear, branched, cyclic, saturated or unsaturated. Substituents when the acyl group is substituted are the same as those in R6, preferably NHCOR12, where R12 is an alkyl group having 1 to 4 carbon atoms, and examples of the alkyl group are the same as those in R6. In the compound of the general formula [1B], examples of the linear or branched aliphatic group having 1 to 6 carbon atoms substituted with NHCOV 1 are methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n -Hexane and an isopropyl group and tert- butyl group are mentioned, Preferably it is a C1-C4 linear aliphatic group, More preferably, it is an ethyl group. In the aliphatic group, at least one hydrogen, preferably one hydrogen, must be substituted with NHCOV1. V represents an alkyl group having 2 to 5 carbon atoms having 4 to 11 halogen atoms. Examples of halogens are fluorine, chlorine, bromine and iodine, preferably fluorine. Specific examples of NHCOV1 substituted alkyl groups are tetrafluoroethyl group, heptafluoro-n-pentyl, nonafluoro-n-butyl and undecafluoro-n-pentyl. In the aliphatic hydrocarbon group, at least one hydrogen, preferably one hydrogen may be substituted with a carboxyl group or a group derived therefrom. Examples of the group derived from a carboxyl group are the same as those described above, preferably, a carboxyl group or C00R13 (wherein R13 is an unsubstituted or substituted alkyl, alkenyl or alkynyl group having 1 to 4 carbon atoms, and examples of these groups include Same as those for), and more preferably a carboxy group. In Y B of the compound represented by the general formula [1B], the aryl group having 3 to 6 carbon atoms means, for example, a benben ring, and the monocyclic aromatic heterocyclic ring having 3 to 6 carbon atoms contains nitrogen, oxygen, or sulfur. 5 or 6 membered ring means. Examples of these substituents when the aromatic hydrocarbon ring or the monocyclic aromatic heterocycle are substituted are the same as those for the aliphatic described above. In Y B of the compound represented by general formula [1B], a methyl group, an ethyl group, n-propyl group, n- is mentioned as an example of the C1-C6 linear or branched aliphatic group substituted by the monocyclic aromatic heterocyclic ring. It is a butyl group, n-pentyl group, n-hexyl group, isopropyl group, and tert- butyl group, Preferably it is a C1-C4 linear aliphatic group, More preferably, it is an ethyl group and n-propyl group. In the aliphatic hydrocarbon group, at least one hydrogen, preferably one hydrogen, must be substituted with a monocyclic aromatic heterocycle. Examples of monocyclic aromatic heterocycles include pyridine, pyrazine, pyrimidine, indole, pyrrole, imidazole, triazole, tetrazole, furan and thiophene rings, preferably pyridine or tetrazole. These heterocycles may be bonded to an aliphatic group via a carbon or nitrogen atom, preferably via a carbon atom. In the case where the heterocycle is substituted, each ring may have 1 to 4, preferably 1 to 2 substituents. Examples of these substituents are alkyl groups having 1 to 4 carbon atoms, preferably methyl groups. At least one hydrogen, preferably one hydrogen in this aliphatic group may be substituted with an amino group or a group derived therefrom. Examples of groups derived from amino groups are as described above, preferably NR15R16 (where R15 and R16 may be the same or different, respectively, independently hydrogen, unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or 1 carbon atom) Unsubstituted or substituted acyl group of -5). In the group represented by NR 15 R 16, examples of the alkyl group and the groups in which the alkyl group is substituted are the same as those for R 6. The acyl group may be linear, branched, cyclic, saturated or unsaturated. When the acyl group is substituted, examples of these groups are the same as those for R 6, preferably NHCOR 17 where R 17 is an alkyl group having 1 to 4 carbon atoms and examples of this alkyl group are the same as those for R 6. . In the compound represented by the general formula [1B], Z B is a carboxy group or a group derived therefrom, a sulfate group or a group derived therefrom, a phosphate group or a group derived therefrom, or an unsubstituted carbon atom having 1 to 4 carbon atoms. Or a substituted alkyl group, hydroxy group, OR1 (where R1 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted or substituted acyl group having 1 to 5 carbon atoms), NHCOR2 (where R2 is 1 to 1 carbon atoms) 4 is an unsubstituted or substituted alkyl group of 4), NHSO 2 R2 '(where R2' is an unsubstituted or substituted alkyl group or phenyl group having 1 to 4 carbon atoms), monocyclic aromatic heterocyclic ring, halogen or hydrogen. Examples of groups derived from carboxyl groups are the same as those described above. Examples of groups derived from sulfate groups are groups derived from sulfonamide derivatives such as SO 2 NH 2 , SO 2 NHCH 3 , SO 2 N (CH 3 ) 2, and SO 2 NHCOCH 3 . Examples of groups derived from phosphate are P (O) (OH) H, P (O) (OH) (NH 2 ) and P (O) (OH) CH (OCH 3 ) 2 . The alkyl group having 1 to 4 carbon atoms, the alkyl group represented by R1, R2 and R2 'and each substituent when these alkyl groups are substituted are the same as those for R6. The acyl group at R 1 and each substituent when this acyl group is substituted are the same as those for R 7. Examples of NHCOR 2 are NHCOCH 3 , NHCOCF 3 and NHCOC 2 H 5 . Examples of NHSO 2 R 2 ′ are NHSO 2 Ph, NHSO 2 CF 3 and NHSO 2 C 2 F 5 . Preferred example of the monocyclic heteroaryl group is 5-tetrazolyl. For Z R , examples of halogen are fluorine, chlorine, bromine and iodine, preferably fluorine and chlorine. Preferred examples of Z are carboxy, COOR3 (wherein R3 is an unsubstituted or alkyl group-substituted carbon atoms from 1 to 4, examples of the alkyl group and the substituent of the alkyl group is the same as those for R6), CH 2 OR4 (wherein R4 is An unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, examples of the alkyl group and substituents of this alkyl group are the same as those for R 6, and CH 2 OCOR 5, wherein R 5 is an unsubstituted or substituted carbon atom having 1 to 4 carbon atoms. An alkyl group, and examples of the alkyl group and substituents of the alkyl group are the same as those for R6), and more preferably carboxyl group, methoxycarbonyl group, hydroxymethyl group and acetyloxymethyl group. [C] Compounds of General Formula [1C] In the present invention, the ring A in the compound represented by the general formula [1C] is a 2-cyclopenten-l-one ring, wherein the Y c -X c -CH 2 component is bonded to carbon by a double bond and is a single ring. Includes bonding to carbon by bonding. In the compound of the present invention represented by the general formula [1C], X c is preferably S, O or SO, most preferably S. In Y c in the compound represented by General Formula [1C], the linear or branched aliphatic group having 1 to 6 carbon atoms includes an alkyl group or an alkenyl group. Examples of the alkyl group include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, isopropyl group and tert-butyl group. Examples of alkenyl groups are vinyl group, 2-propenyl group, isopropenyl group and 2-butenyl group. The aliphatic hydrocarbon group is preferably an alkyl group having 1 to 4 carbon atoms, more preferably an ethyl group. The aliphatic hydrocarbon group may be substituted or unsubstituted. When an aliphatic hydrocarbon group is substituted, you may contain 1-6 substituents, Preferably you may contain 1-4. These substituents include carboxyl groups or groups derived therefrom, amino groups or groups derived therefrom and hydroxy groups or groups derived therefrom. A monocyclic aromatic heterocyclic ring or aromatic hydrocarbon ring having 3 to 6 carbon atoms means an aromatic heterocyclic ring such as a 5- or 6-membered ring containing nitrogen, oxygen or sulfur, and an aromatic hydrocarbon ring such as a benzene ring. When an aromatic hydrocarbon ring or an aromatic hetero ring is substituted, examples of these substituents are the same as those for an aliphatic hydrocarbon group. The groups derived from carboxyl groups are derived from carboxyl functional groups such as esterified or amidated carboxyl groups, cyano groups, hydroxymethyl groups or aminomethyl groups produced by reducing these substituents, and by modification such as acylation or alkylation of functional groups. It includes a functional group. Preferably, the carboxyl group or group derived therefrom is a carboxyl group, COOR1 (where R1 is an unsubstituted or substituted alkyl or alkenyl group having 1 to 4 carbon atoms), CONR2R3 (where R2 and R3 may be the same or different, respectively, independently Hydrogen or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms) and COW, wherein W is an unsaturated or saturated heterocyclic ring. Here, the alkyl group represented by R1 in COOR1 may be linear, branched or cyclic. Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, cyclopropyl group, n-butyl group, isobutyl group, tert-butyl group and cyclobutyl group, and preferably methyl group, ethyl group and n-propyl group More preferably, it is a methyl group. Examples of the alkenyl group include a vinyl group, 2-propenyl group, isopropenyl group and 2-butenyl group. When substituted, for example, 1 to 6 substituents, preferably 1 to 3 substituents may be present. Examples of these substituents are halogen, hydroxy group, thiol group, carboxy group, methoxycarbonyl group, acetyloxy group, acetylthio group, cyano group and acetylamino group. Examples of halogens are bromine, chlorine and fluorine. It is preferable that the substituent in R1 is unsubstituted. When the alkyl group represented by R2 or R3 and its substituent (s) are substituted, examples of these substituents are the same as those for R1. Preferably, W represents a saturated heterocycle, more preferably an azetidine, pepperidine, pyrrolidine, piperazine or morpholine ring. These heterocycles may be bonded to a carbonyl group via carbon or nitrogen, and are preferably bonded to a carbonyl group via nitrogen. When a heterocycle is substituted, 1 to 4 substituents, preferably 1 to 2 substituents may be present in each ring. Examples of these substituents are carboxyl groups or groups derived therefrom and amino groups or groups derived therefrom. These groups are demonstrated. Examples of groups derived from amino groups include functional groups in which the amino groups are alkylated or acylated, nitro groups, hydroxyamino groups, imino groups, and heterocyclic groups containing nitrogen atoms of the amino groups, preferably NR4R5 (where R4 and R5 May be the same as or different from each other, and independently represent hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms). In the group represented by NR 4 R 5, the alkyl group at R 4 and R 5 and each substituent when the alkyl group is substituted are the same as those at R 1. The acyl group in R4 and R5 may be linear, branched, cyclic, saturated or unsaturated. Representative examples of the acyl group are acetyl group, propionyl group, acroyl group, propiolyl group, n-butyryl group, isobutyryl group, crotonoyl group, valeryl group, isovaleryl group and pivaloyl group. When the acyl group is substituted, the substituents are the same as those in R1. The group derived from the amino group is preferably NHCOR 14, where R 14 is an alkyl group having 1 to 4 carbon atoms, wherein the hydrogen (s) may be substituted with fluorine; examples of this alkyl group are the same as those in R 1. The number of fluorine atoms which may be substituted is 1-9, Preferably it is 1-7. Most preferably, R 14 is a methyl group. Examples of groups derived from hydroxy groups include functional groups in which the hydroxy group is alkylated or acyl, keto and halogen, preferably OCOR15 (where R15 is an alkyl group having 1 to 4 carbon atoms, examples of which are those in R1) Is the same as. In the cyclopentenone derivative of the general formula [1C], each of Z1 C , Z2 C and Z3 C is a carboxyl group or a group derived therefrom, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or an alkenyl group, a hydroxy group or a To a group derived from, an amino group or a group derived therefrom, a monocyclic aromatic heterocycle, halogen or hydrogen. Examples of the group derived from a carboxyl group, an amino group or a hydroxy group are the same as described above. Each substituent in the case where an alkyl group and an alkenyl group and this alkyl group and alkenyl group are substituted is the same as that for A. Preferred examples of Z1 C , Z2 C and Z3 C include carboxyl group, COOR7 (where R7 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), cyano group, hydroxy group, CH 2 OR10 (where R10 is hydrogen, carbon atom) An unsubstituted or substituted alkyl group of 1 to 4 or an unsubstituted or substituted acyl group of 1 to 5 carbon atoms, OCOR11 (where R11 is an unsubstituted or substituted alkyl group of 1 to 4 carbon atoms), NR12R13 (where R12 And R13 may be the same as or different from each other, and independently hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms), 5-tetrazolyl group, chlorine , Fluorine or hydrogen. The alkyl group at R7, R8, R9, R10, R11, R12 and R13, and each substituent when the alkyl group is substituted are the same as those for R1. In addition, the acyl group in R10, R12, and R13 and each substituent when this acyl group is substituted are the same as those for R4. Preferred combinations of R12 and R13 are those in which R12 is hydrogen and R13 is an acetyl group. Examples of halogens are fluorine, chlorine, bromine and iodine, with fluorine and chlorine being preferred. Preferred examples of the substituents Z 1 C , Z 2 C and Z 3 C are those when all of the substituents are hydrogen or one or two substituents are substituents other than hydrogen. More preferred examples of these substituents include carboxyl group, except for hydrogen, COOR7 '(where R7' is an alkyl group having 1 to 4 carbon atoms) and CH 2 OR10 '(where R10' is hydrogen, 1 to 5 carbon atoms) Ring or a substituted acyl group). Examples of R7 'are the same as those in R1. Examples of acyl groups at R 10 ′ are the same as those at R 4, most preferably a carboxyl group, methoxycarbonyl group, hydroxymethyl group and acetyloxymethyl group. [D] A compound of the general formula [1D] In the ketone derivative of the present invention represented by general formula [1D], an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 4 carbon atoms represented by A D is an alkyl group having 1 to 4 carbon atoms or optionally substituted. It means a kenyl group. Examples of the alkyl group include methyl group, ethyl group, n-propyl group, n-butyl group, isopropyl group, cyclopropyl group and tert-butyl group. Examples of the alkenyl group include a vinyl group, 2-propenyl group, isopropenyl group and 2-butenyl group. Examples of preferred aliphatic hydrocarbon groups are methyl group, ethyl group, n-propyl group and isopropyl group, and methyl group is more preferable. The aliphatic hydrocarbon group may be unsubstituted or substituted. When an aliphatic group is substituted, 1-6 substituents, for example, 1-3 may exist preferably. Examples of these substituents are halogen, hydroxy group, thiol group, carboxyl group, methoxycarbonyl group, acetoxy group, acetylthio group, cyano group and acetylamino group. Examples of halogens are bromine, chlorine and fluorine. Preferably, the aliphatic hydrocarbon group is unsubstituted. Examples of the unsubstituted or substituted aromatic hydrocarbon ring, aromatic heterocycle, or saturated heterocycle represented by A D in the compound of the formula [1D] are benzene, 1-naphthalene, 2-naphthalene, thiophene, furan, pyrrole, and imidazole. , Oxazole, pyrazole, isoxazole, pyridine, pyrazine, indane, quinoline, isoquinoline, quinazoline, coumarin, pyrrolidine, piperidine or piperazine ring, preferably benzene ring and monocyclic aromatic hetero Ring, more preferably a benzene ring. These rings may be unsubstituted or substituted. In the case of substitution, 1-6 substituents, Preferably 1-3 may exist in each ring. Examples of these substituents include alkyl groups having 1 to 4 carbon atoms, halogen, hydroxy groups, alkyloxy groups having 1 to 4 carbon atoms, amino groups, monoalkylamino groups having 1 to 4 carbon atoms or dialkylamino groups, thiol groups, carboxy groups and carbon atoms And an alkyloxycarbonyl group having 1 to 4 carbon atoms, an acyloxy group having 1 to 5 carbon atoms, an acylthio group having 1 to 5 carbon atoms, an acylamino group having 1 to 5 carbon atoms, a cyano group and a trifluoromethyl group. Examples of halogens are bromine, chlorine and fluorine. The alkyl components in the alkyl group having 1 to 4 carbon atoms and the acyl group having 1 to 5 carbon atoms are the same as those for A. Preferred examples of A D are unsubstituted ones and those in which a methyl group, methoxy group, methoxycarbonyl group, nitro group, cyano group, halogen or trifluoromethyl group are substituted for one to three hydrogen atoms. In the ketone derivative of the general formula [1D], examples of the unsubstituted or substituted aliphatic group B D having 1 to 4 carbon atoms are the same as those for A D , preferably hydrogen or methyl group. In ketone derivatives of the general formula [1D], A D and B D are bonded together to form an unsubstituted or substituted cycloalkane-1-one ring having 3 to 7 carbon atoms (excluding the ring having 5 carbon atoms) Examples of such a ring include a cyclopropanone ring, a cyclobutanone ring, a cyclohexanone ring and a cycloheptanone ring, and preferably a cyclobutanone ring and a cyclohexanone ring. Except in the case of substitution in General Formula [1D], the cycloalkane-1-one ring may be unsubstituted or substituted. When a ring is substituted, 1 to 4 substituents, preferably 1 to 2 substituents may be present in each ring. Examples of these substituents are halogen, hydroxy group, thiol group, carboxy group, methoxycarbonyl group, hydroxymethyl group, acetoxymethyl group, cyano group and acetylamino group. Examples of halogens are the same as those for A D. It is preferable that the ring is unsubstituted. In the ketone derivative of the present invention represented by general formula [1D], X D is preferably S, O or SO, most preferably S. In Y D in the ketone derivative represented by the general formula [1D], the linear or branched aliphatic hydrocarbon group having 1 to 6 carbon atoms includes an alkyl group or an alkenyl group. Examples of the alkyl group are methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl, isopropyl group and tert-butyl group. Examples of the alkenyl group include a vinyl group, 2-propenyl group, isopropenyl group and 2-butenyl group. Preferred aliphatic groups are alkyl groups having 1 to 4 carbon atoms, more preferably ethyl groups. The aliphatic hydrocarbon group may be unsubstituted or substituted. When an aliphatic hydrocarbon group is substituted, this group may contain 1-6 substituents, Preferably 1-4. Examples of these substituents are carboxyl groups or groups derived therefrom, amino groups or groups derived therefrom, hydroxy groups or groups derived therefrom. A monocyclic aromatic heterocyclic ring or aromatic hydrocarbon ring having 3 to 6 carbon atoms means an aromatic hydrocarbon ring such as a benzene ring and an aromatic heterocycle such as a 5-membered ring or a 6-membered ring containing nitrogen, oxygen or sulfur. When aromatic hydrocarbon rings or monocyclic aromatic hetero rings are substituted, examples of these substituents are the same as those for aliphatic hydrocarbon groups. The groups derived from carboxyl groups are derived from carboxyl functional groups such as esterified or amidated carboxyl groups, cyano groups, hydroxymethyl groups or aminomethyl groups produced by reducing these substituents, and by modification such as acylation or alkylation of functional groups. It includes a functional group. Preferably, the carboxyl group or group derived therefrom is a carboxyl group, COOR1 (where R1 is an unsubstituted or substituted alkyl or alkenyl group having 1 to 4 carbon atoms), CONR2R3 (where R2 and R3 may be the same or different, respectively, independently Hydrogen or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms) and COW, wherein W is an unsubstituted or substituted heterocyclic ring. Here, the alkyl group represented by R1 in COOR1 may be linear, branched or cyclic. Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, cyclopropyl group, n-butyl group, isobutyl group, tert-butyl group and cyclobutyl group, and preferably methyl group, ethyl group and n-propyl group More preferably, it is a methyl group. Examples of the alkenyl group include a vinyl group, 2-propenyl group, isopropenyl group and 2-butenyl group. When the alkyl group or the alkenyl group is substituted, for example, 1 to 6 substituents, preferably 1 to 3 substituents may be present. Examples of these substituents are halogen, hydroxy group, thiol group, carboxy group, methoxycarbonyl group, acetyloxy group, acetylthio group, cyano group and acetylamino group. Examples of halogens are the same as defined for A. It is preferred that the alkyl at R 1 is unsubstituted. When the alkyl group represented by R2 or R3 and its substituent (s) are substituted, examples of these substituents are the same as those defined for R1. Preferably, W represents a saturated heterocycle, more preferably an azetidine, pepperidine, pyrrolidine, piperazine or morpholine ring. These heterocycles may be bonded to a carbonyl group via carbon or nitrogen, and are preferably bonded to a carbonyl group via nitrogen. When a heterocycle is substituted, 1 to 4 substituents, preferably 1 to 2 substituents may be present in each ring. Examples of these substituents are carboxyl groups or groups derived therefrom and amino groups or groups derived therefrom. These substituents are demonstrated. Examples of groups derived from an amino group include heterocyclic groups containing a functional group in which the amino group is alkylated or acylated, a sulfonylated nitro group, a hydroxyamino group, an imino group, and a nitrogen atom derived from an amino group, preferably NR4R5 (where R4 and R5 may be the same as or different from each other, and are each independently hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms). In the group represented by NR 4 R 5, the alkyl group at R 4 and R 5 and each substituent when the alkyl group is substituted are the same as those defined for R 1. The acyl group in R4 and R5 may be linear, branched, cyclic, saturated or unsaturated. Representative examples of the acyl group are acetyl group, propionyl group, acroyl group, propiolyl group, n-butyryl group, isobutyryl group, crotonoyl group, valeryl group, isovaleryl group and pivaloyl group. When the acyl group is substituted, the substituents are the same as those defined for R 1. The group derived from the amino group is preferably NHCOR 14, where R 14 is an alkyl group having 1 to 4 carbon atoms, in which the hydrogen (s) may be substituted with fluorine; examples of this alkyl group are the same as those defined for R 1. The number of fluorine atoms which may be substituted is 1-9, Preferably it is 1-7. Most preferably, R 14 is a methyl group. Examples of groups derived from hydroxy groups include functional groups in which the hydroxy group is alkylated or acyl, keto and halogen, preferably OCOR15 (where R15 is an alkyl group having 1 to 4 carbon atoms, examples of which are defined for R1) Same as the ones). Z D in the ketone derivative [1D] of the present invention is a carboxyl group or a group derived therefrom, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or an alkenyl group, a hydroxy group or a group derived therefrom, an amino group or a derivative thereof Derived groups, sulfate groups or groups derived therefrom, phosphate groups or groups derived therefrom, monocyclic aromatic heterocycles, halogens or hydrogen. Examples of groups derived from carboxyl groups, amino groups or hydroxy groups are the same as those defined above. Groups derived from amino groups further include NHSO 2 Ph, NHCOCF 3 , NHCOC 2 H 5 , NHSO 2 CF 3 and NHSO 2 C 2 F 5 . The alkyl group and the alkenyl group and each substituent in the case where this alkyl group or alkenyl group is substituted are the same as those defined for A D. Examples of groups derived from sulfate groups are groups derived from sulfonamide derivatives such as SO 2 NH 2 , SO 2 NHCH 3 , SO 2 N (CH 3 ) 2, and SO 2 NHCOCH 3 . Examples of groups derived from phosphate are P (O) (OH) H, P (O) (OH) (NH 2 ) and P (O) (OH) CH (OCH 3 ) 2 . Preferred examples of Z D include a carboxy group, COOR7 (where R7 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), and CONR8R9 (where R8 and R9 may be the same or different, respectively, independently hydrogen or 1 carbon atom). A cyano group, a hydroxy group, CH 2 OR 10, wherein R 10 is hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or an unsubstituted or substituted carbon atom having 1 to 5 carbon atoms Acyl), OCOR11 (where R11 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), NR12R13 (where R12 and R13 may be the same or different, respectively, independently hydrogen, 1 to 4 carbon atoms) Ring or substituted alkyl group or unsubstituted or substituted acyl group having 1 to 5 carbon atoms), 5-tetrazolyl group, halogen or hydrogen. Examples of the alkyl group at R7, R8, R9, R10, R11, R12, and R13 and the substituents when the alkyl group is substituted are the same as those defined for R1. In addition, the acyl group represented by R10, R12, and R13 and the example of each substituent in the case where an acyl group is substituted are the same as those defined about R4. Preferred combinations of R12 and R13 are those in which R12 is hydrogen and R13 is an acetyl group. Examples of halogens are fluorine, chlorine, bromine and iodine, with fluorine and chlorine being preferred. More preferred examples of the substituent Z D include a carboxyl group, COOR7 '(where R7' is an alkyl group having 1 to 4 carbon atoms) and CH 2 OR10 '(where R10' is hydrogen, an unsubstituted or substituted group having 1 to 5 carbon atoms). Practical). Examples of R7 'are the same as those in R1. Examples of acyl groups at R 10 ′ are the same as those at R 4, most preferably a carboxyl group, methoxycarbonyl group, hydroxymethyl group and acetyloxymethyl group. [E] Compounds of General Formula [1E] The compound of general formula [1E] is represented by general formula [1E] mentioned above. [F] Compounds of General Formula [1F] In the compound of the present invention represented by General Formula [1F], an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 4 carbon atoms represented by A F may be optionally substituted an alkyl or alkenyl group having 1 to 4 carbon atoms. to be. Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group and tert-butyl group. Examples of the alkenyl group include a vinyl group, 2-propenyl group, isopropenyl group and 2-butenyl group. Examples of preferred aliphatic hydrocarbon groups are methyl group, ethyl group, n-propyl group and isopropyl group, and methyl group is more preferable. The aliphatic hydrocarbon group may be unsubstituted or substituted. When an aliphatic group is substituted, 1-6 substituents, for example, 1-3 may exist preferably. Examples of these substituents include alkyl groups having 1 to 4 carbon atoms, halogen, hydroxy groups, alkyloxy groups having 1 to 4 carbon atoms, amino groups, monoalkylamino groups having 1 to 4 carbon atoms or dialkylamino groups, nitro groups, cyano groups, and tri Fluoromethyl group, carboxy group, alkyloxycarbonyl group having 1 to 4 carbon atoms, acyloxy group having 1 to 5 carbon atoms, acylthio group having 1 to 5 carbon atoms, and acylamino group having 1 to 5 carbon atoms. Examples of halogens are bromine, chlorine and fluorine. Examples of the alkyl group having 1 to 4 carbon atoms and the alkyl group having 1 to 4 carbon atoms in the acyl group having 1 to 5 carbon atoms are the same as those defined for A F. Examples of the unsubstituted or substituted aromatic hydrocarbon ring, aromatic heterocycle, or saturated heterocyclic ring represented by A F in the compound of the formula [1F] include benzene, 1-naphthalene, 2-naphthalene, thiophene, furan, pyrrole, imidazole, Oxazoles, pyrazoles, isoxazoles, pyridine, pyrazine, indane, quinoline, isoquinoline, quinazoline, coumarin, pyrrolidine, piperidine 을 include piperazine rings, preferably benzene rings and monocyclic rings It is an aromatic hetero ring, More preferably, it is a benzene ring. These rings may be unsubstituted or substituted. When a ring is substituted, 1-6 substituents, Preferably 1-3 may exist in each ring. Examples of these substituents include alkyl groups having 1 to 4 carbon atoms, halogen, hydroxy groups, alkoxy groups having 1 to 4 carbon atoms, amino groups, monoalkylamino groups having 1 to 4 carbon atoms or dialkylamino groups, thiol groups, carboxyl groups and 1 carbon atoms An alkoxycarbonyl group of 4 to 4, an acyloxy group of 1 to 5 carbon atoms, an acylthio group of 1 to 5 carbon atoms, an acylamino group of 1 to 5 carbon atoms, a cyano group and a trifluoromethyl group. Examples of halogens are bromine, chlorine and fluorine. Examples of the alkyl component in the alkyl group having 1 to 4 carbon atoms and the acyl group having 1 to 5 carbon atoms are the same as those for A. Preferred examples of A F are unsubstituted ones and those in which a methyl group, methoxy group, methoxycarbonyl group, nitro group, cyano group, halogen or trifluoromethyl group are substituted for one to three hydrogen atoms. In the compound of the general formula [1F], examples of the unsubstituted or substituted aliphatic hydrocarbon group B F having 1 to 4 carbon atoms are the same as those for A F. In the compound of the general formula [1F], A F and B F are bonded together to form an unsubstituted or substituted cycloalkane-1-one having 3 to 7 carbon atoms. Examples of the ring include a cyclopropane-1-one ring, a cyclobutan-1-one ring, a cyclopentan-1-one ring, a cyclohexane-1-one ring and a cycloheptan-1-one ring, preferably cyclobutan-1- It is an on-ring, a cyclopentan-1-one ring, and a cyclohexane-1-one ring, More preferably, it is a cyclopentan-1-one ring. These rings may be unsubstituted or substituted. When a ring is substituted, 1 to 2 substituents may exist in each ring. Examples of these substituents are halogen, hydroxy, carboxy, methoxycarbonyl group, acetoxy group, acetylthio group, cyano group and acetylamino group. Examples of halogens are bromine, chlorine and fluorine. As an example which has two substituents, the fused ring with an aromatic hydrocarbon ring or an aromatic hetero ring is typical. Examples of the aromatic hydrocarbon ring formed by A F and B F are a benzene ring and a naphthalene ring. Examples of aromatic heterocycles include 6-membered aromatic heterocycles such as pyridine ring, pyrazine ring or pyrimidine ring and 5-membered heteroaryl such as thiophene, pyrrole, furan, oxazorthiazole, isoxazole, isothiazole or azole ring to be. As the group formed by A F and B F , an aromatic hydrocarbon ring is preferable, and more preferably a benzene ring. When this ring is substituted, examples of the substituent include unsubstituted alkyl groups such as ethyl group, n-propyl group and isopropyl group, or alkyl groups substituted with halogen (eg fluorine) such as trifluoromethyl group. Alkyl groups; Alkyloxy groups having 1 to 4 carbon atoms such as a methoxy group or an ethoxy group; Nitro groups and halogens such as fluoro, chlorine or bromine. Specific examples are indan-1-one, 6,7-dihydro-5-oxocyclopenta [b] pyridine and 5,6-dihydro-7-oxocyclopenta [b] pyridine, preferably indan-1 -On. In the compound of the present invention represented by general formula [1F], the linear or branched aliphatic hydrocarbon group having 1 to 10 carbon atoms represented by X F or Y F means an alkyl group or alkenyl group having 1 to 10 carbon atoms. . Preferably, the aliphatic hydrocarbon group is an alkyl group having 1 to 6 carbon atoms, and examples of the alkyl group are ethyl group, n-propyl group, n-butyl group, n-pentyl, n-hexyl, isopropyl group and isobutyl group. Preferably they are ethyl group, n-propyl group, and isopropyl group, Most preferably, they are ethyl group. Aliphatic groups may be unsubstituted or substituted. When the aliphatic group is substituted, the aliphatic group may contain 1 to 6 substituents, preferably 1 to 3 substituents. Examples of these substituents are carboxyl groups or groups derived therefrom, amino groups or groups derived therefrom, hydroxy groups or groups derived therefrom. Groups derived from carboxyl groups are esterified or amidated carboxyl groups (e.g. -COOR1, -COOR1 ', -COOR1 ", -CONR2R3, -CONR2'R3', -CONR2" R3 ", etc., described below), cyano groups And a carboxyl functional group such as an aminomethyl group or a hydroxymethyl group generated by reduction of these functional groups, or a functional group induced by modification such as acylation of a functional group (eg, -CH 2 OR4, -CH 2 OR4 '). Examples of the group derived from the amino group include a heterocyclic group containing a nitrogen group derived from an alkyl group, an alkylated, acylated or sulfonylated group (e.g., -NR6R7 described above), a nitro group, a hydroxyamino group, an imino group, and an amino group. Include. Examples of groups derived from hydroxy groups include functional groups which have alkylated or acylated hepoxy groups (eg -OR 5 described above), ketos and halogens. In the compounds of the present invention represented by the general formula [1F], examples of the heterocyclic group formed by directly bonding X F and Y F to each other or through a hetero atom include pyrrole, imidazole, indole, indazole, purine, carr Basezol, imidazolidine, imidazoline, pyrrolidine, piperidine, piperazine, morpholine and indole rings. Preferred heterocyclic groups are monocyclic heterocycles such as pyrrole, imidazole, imidazole, imidazolidine, imidazoline, pyrrolidine, piperidine, piperazine and morpholine rings, more preferably pyrrolidine And saturated monocyclic hetero rings such as piperidine and morpholine rings. These rings may be unsubstituted or substituted. When the ring is substituted, for example, each ring may have 1 to 6 substituents, preferably 1 to 3 substituents. Examples of these substituents include alkyl groups having 1 to 4 carbon atoms, phenyl groups, carboxyl groups or groups derived therefrom, amino groups or groups derived therefrom, hydroxy groups or groups derived therefrom. Examples of groups derived from carboxyl groups, amino groups or hydroxy groups are as described above. Preferable examples of these substituents are an alkyl group having 1 to 4 carbon atoms and a phenyl group, more preferably a methyl group and a phenyl group. Preferred examples of the substituted heteroaryl group are imidazolidine ring and piperazine ring, and more preferably 4-methylpiperazine ring and 4-phenylpiperazine ring. In the compound of the present invention represented by general formula [1F], Z F is a carboxyl group or a group derived therefrom, an unsubstituted or substituted alkyl or alkenyl group having 1 to 4 carbon atoms, a hydroxyl group or a group derived therefrom, Amino groups or groups derived therefrom, sulfate groups or groups derived therefrom, phosphate groups or groups derived therefrom, monocyclic aromatic heteroaryl groups or halogens. Examples of groups derived from carboxyl groups, amino groups or hydroxy groups are as described above. Examples of groups derived from amino groups further include NHSO 2 Ph, NHCOCF 3 , NHCOC 2 H 5 , NHSO 2 CF 3 and NHSO 2 C 2 F 5 . Examples of groups derived from sulfate groups are groups derived from sulfonamide derivatives such as SO 2 NH 2 , SO 2 NHCH 3 , SO 2 N (CH 3 ) 2, and SO 2 NHCOCH 3 . Examples of groups derived from phosphate are P (O) (OH) H, P (O) (OH) (NH 2 ) and P (O) (OH) CH (OCH 3 ) 2 . Examples of the alkyl group having 1 to 4 carbon atoms are methyl group, ethyl group, n-propyl group, isopropyl group and n-butyl group. Examples of the alkenyl group having 1 to 4 carbon atoms are a vinyl group, 2-propenyl group, isopropenyl group and 2-butenyl group. When an alkyl group or an alkenyl group is substituted, examples of these substituents are the same as defined for the aliphatic group in A F. Examples of monocyclic heteroaryl groups include 5-tetrazolyl, 3- (4H-5-oxo-1,2,4-oxadiazolyl), 5- (3-hydroxyisoxazolyl), 5- (3- Hydroxyisothiazolyl) and 4- (3-hydroxy-1,2,5-thiadiazolyl). Examples of halogens are fluorine, chlorine, bromine and iodine. More preferred examples of Z F are carboxyl group, COOR1 (where R1 is an unsubstituted or substituted alkyl or phenyl group having 1 to 4 carbon atoms), CONR2R3 (where R2 and R3 may be the same or different, respectively, independently hydrogen or carbon source A substituted or unsubstituted alkyl group of 1 to 4 embroidery, a cyano group, CH 2 OR4 (where R 4 is hydrogen, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted acyl group having 1 to 5 carbon atoms) ), -OR5 (where R5 is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted acyl group having 1 to 5 carbon atoms), 5-tetrazolyl, chlorine and fluorine. Examples of the substituent of the alkyl group and the acyl group are the same as those defined for the substituent of the aliphatic group represented by A F. Examples of more preferred A F include a carboxy group, COOR1 '(where R1' is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), CONR2'R3 '(where R2' and R3 'may be the same or different, respectively, and are independent. Is hydrogen or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, a cyano group and CH 2 OR4 '(where R4' is hydrogen, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or substituted with 1 to 5 carbon atoms) Or an unsubstituted acyl group). As a particularly preferred example Z F is a carboxy group, COOR1 "(where R" is a methyl group or an ethyl group), CONR2 "R3" (where R2 "and R3" may be the same or different, respectively, independently hydrogen, methyl or ethyl group) and It contains a cyano group. Preferred examples of the compounds according to the invention are as follows. Compound of general formula [1A] (1A) trans-4-{(2R) -2-acetylamino-2-carboxyethylthio} methyl-3-oxo-1-cyclopentanecarboxylic acid; (2A) trans-4-{(2R) -2-acetylamino-2-methoxycarbonylethylthio} methyl-3-oxo-1-cyclopentanecarboxylic acid; (3A) 2RS, 4S) -2-{(2R) -2-acetylamino-2-carboxyethylthio} methyl-4-hydroxy-1-cyclopentanone; (4A) 2RS, 4S) -2-{(2R) -3-acetylamino-3- {1-{(2S) -2-methoxycarbonyl} pyrrolidinyl] -3-oxypropylthio} methyl- 4-hydroxy-1-cyclopentanone; (5A) 2-{(2R) -2-acetylamino-2-carboxyethylthio} methyl-3-oxo-1-indanecarboxylic acid; (6A) 2-{(2R) -2-acetylamino-2-methoxycarbonylethylthio} methyl-3-oxo-1-indanecarboxylic acid; Compound of general formula [1B] (1B) (1R, 2S) -2-[(2R)-{2-acetylamino-3-oxo-3- (1-pyrrolidinyl)} propyl Thio] methyl-3-oxo-1-cyclopentanecarboxylic acid; (2B) (1R, 2S) -2-[(2R)-{2-acetylamino-3- (4-morpholino) -3-oxo} propyl Thio] methyl-3-oxo-1-cyclopentanecarboxylic acid; (3B) (1R, 2S) -2-[(2R)-{2-acetylamino-3-oxo-3- (1-piperidinyl)} propyl Thio] methyl-3-oxo-1-cyclopentanecarboxylic acid; (4B) (1R, 2S) -2-[(2R)-({2-carboxy-2-pentafluoropropionylamino) ethylthio] methyl-3-oxo-1-cyclopentanecarboxylic acid; (5B) trans-2-[(2R)-{2-acetylamino-3-oxo-3- (1-pyrrolidinyl)} propyl Thio] methyl-3-methoxycarbonyl-1-cyclopentanone; (6B) trans-2-[(2R)-[2-acetylamino-3- {1-((2S) -2-methoxycarbonylpyrrolidinyl)}-3-oxo] propylthio] methyl-3 Oxo-1-cyclopentanecarboxylic acid; (7B) trans-2-[(2R)-{2-acetylamino-3- {1-((2S) -2-methoxycarbonylazetidinyl)}-3-oxo] propylthio] methyl-3 Oxo-1-cyclopentanecarboxylic acid; (8B) trans-2-[(2R)-(2-carboxy-2-pentafluoropropionylamino) ethyl Thio] methyl-3-hydroxymethyl-1-cyclopentanone; (9B) trans-2-[(11-acetylamino-11-carboxy) undecylthio] methyl-3-oxo-1-cyclopentanecarboxylic acid; (10B) (1R, 2S) -2-[(2R)-{2-acetylamino-3-oxo-3- (1-piperazinyl) propyl Thio}] methyl-3-oxo-1-cyclopentanecarboxylic acid; (11B) (1R, 2S) -2-[(2R)-{2-acetylamino-3-oxo-3- (1- (4-hydroxymethyl) Piperazinyl) propylthio}] methyl-3-oxo-1-cyclopentanecarboxylic acid; (12B) (1R, 2S) -2-[(2R)-{2-acetylamino-3-oxo-3- (1- (4-tert-butoxycar Carbonyl) piperazinyl) propylthio}] methyl-3-oxo-1-cyclopentanecarboxylic acid; (13B) (1R, 2S) -2-[(2R)-[2-acetylamino-3-oxo-3- {1- (4-phenyl) piperazinyl} propylthio)] methyl-3-oxo- 1-cyclopentanecarboxylic acid; (14B) (1R, 2S) -2- {3- (3-pyridyl) propylthio} methyl-3-oxo-1-cyclopentanecarboxylic acid; (15B) (1R, 2S) -2- [3- {3- (1-methylpyridinium iodide)} propylthio} methyl-3- Oxo-1-cyclopentanecarboxylic acid; (16B) (1R, 2S) -2- [2-acetylamino-2- (5-tetrazolyl) ethylthio] methyl-3-oxo-1-cyclopentanecarboxylic acid; Compound of general formula [1C] (1C) 5-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-2-cyclopenten-l-one; (2C) (4R) -2-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-4-hydroxy-2-cyclopenten-l-one; (3C) 2-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-3-hydroxy-2-cyclopenten-1-one; (4C) 5-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-4-carboxy-2-cyclopenten-1-one; (5C) 5-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-4-methoxycarbonyl -2-cyclopenten-l-one; (6C) 5-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-4-hydroxymethyl -2-cyclopenten-l-one; (7C) 5-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-4-acetoxymethyl -2-cyclopenten-l-one; (8C) 5-[(2R)-(2-acetylamino-2-methoxycarbonyl) ethylthio] methyl-4-carboxy -2-cyclopenten-l-one; (9C) 5-[(2-acetylamino) ethylthio] methyl-4-carboxy-2-cyclopenten-1-one; (10C) 2-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-3-carboxy-2- Cyclopenten-l-one; (11C) 2-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-3-methoxycarbo Nile-2-cyclopenten-l-one; (12C) 2-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-3-hydroxymethyl -2-cyclopenten-l-one; (13C) 2-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-3-acetoxymethyl-2-cyclopenten-1-one; (14C) 2-[(2R)-(2-acetylamino-2-methoxycarbonyl) ethylthio] methyl-3-carboxy Cy-2-cyclopenten-l-one; (15C) 2-[(2-methoxycarbonyl) ethylthio] methyl-3-carboxy-2-cyclopenten-1-one; (16C) 2-[(2-acetylamino) ethylthio] methyl-3-carboxy-2-cyclopenten-1-one; Compound of formula [1D] (1D) 3-{(2R) -2-acetylamino-2-carboxyethylthio} methyl-4-oxo-1-n-pentanoic acid; (2D) 3-{(2R) -2-acetylamino-2-methoxycarbonylethylthio} methyl-4-oxo-1-n-pentanoic acid; (3D) trans-2-{(2R) -2-acetylamino-2-methoxycarbonylethylthio} methyl-3-ethoxycarbonyl-1-cyclobutanone; (4D) trans-2-{(2R) -2-acetylamino-2-carboxyethylthio} methyl-3-oxo-1- Cyclobutanecarboxylic acid; (5D) 2- (2,3-dihydroxy-n-propyl) thiomethyl-3-acetoxymethyl-1-cyclopart Tan temperature; (6D) 2-{(2R) -2-acetylamino-2-carboxyethylthio} methyl-3-oxo-1-cyclohexanecarboxylic acid; (7D) 3-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-4-oxo-4-phenylbutyric acid; (8D) 3-[(2R)-(2-acetylamino-2-methoxycarbonyl) ethylthio] methyl-4-oxo-4-phenylbutyric acid; (9D) 3-[(2R)-(2-acetylamino-2-methoxycarbonyl) ethylthio] methyl-4- (4-methoxyphenyl) -4-oxobutyric acid; (10D) 3- {2- (acetylamino) ethylthio} methyl-4- (4-methoxyphenyl) -4-oxobuty Leric acid; (11D) 3- {2- (acetylamino) ethylthio} methyl-4-oxo-4-phenylbuty Leric acid; (12D) 3- {2- (acetylamino) ethylthio} methyl-4- (4-methylphenyl) -3-oxobuty Leric acid; (13D) 3-{(2R)-(2-acetylamino-2-methoxycarbonyl) ethylthio} methyl-4- (4- Methylphenyl) -3-oxobutyric acid; (14D) 3-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-4-oxo-4- (4-trifluoromethylphenyl) butyric acid; (15D) 3-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-4-oxo-4- (2-trifluoromethylphenyl) butyric acid; (16D) 3-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-4-oxo-4- (3-trifluoromethylphenyl) butyric acid; (17D) 3-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-4-oxo-4- (3-pyridyl) butyric acid; (18D) 3-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-4-oxo-4- (2-pyridyl) butyric acid; (19D) 3-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-4-oxo-4- (4-pyridyl) butyric acid; (20D) 3-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-4- (1-naphthyl) -4-oxobutyric acid; (21D) 3-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-4- (2-naphthyl) -4-oxobutyric acid; (22D) 3-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-4-oxo-4- (1-piperidyl) butyric acid; (23D) 3-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-4- (4-methyl-1-piperazinyl) -4-oxobutyric acid; (24D) 3-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-4-oxo-4- (4- Phenyl-1-piperazinyl) butyric acid; (25D) 3-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-4- (2-furyl) -4- Oxobutyric acid; (26D) 3-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-4- (3-furyl) -4- Oxobutyric acid; (27D) 3-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-4-oxo-4- (2-thienyl) butyric acid; (28D) 3-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-4-oxo-4- (3-thienyl) butyric acid; (29D) 3-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-4-oxo-4- (2-pyrrolyl) butyric acid; (30D) 3-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-4-oxo-4- (3-pyrrolyl) butyric acid; (31D) 3-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-4- (2-imida Zolyl) -4-oxobutyric acid; (32D) 3-[(2R)-(2-acetylamino-2-methoxycarbonyl) ethylthio] methyl-4-oxo-4 -(3-pyridyl) butyric acid; (38D) 4-[(2R)-{(2-acetylamino-2-carboxy) ethylthio}] methyl-5-oxo-5- Phenylpentanoic acid; Compound of formula [1E] (1E) (1R, 2S) -2- [N- (pantoyl--alanylamido) ethylthio] methyl-3-oxo-1-cycl Lofentancarboxylic acid; Compound of general formula [1F] (1F) 4-oxo-4-phenyl-3- (1-piperidyl) methylbutyric acid; (2F) 4- (4-methylphenyl) -4-oxo-3- (1-piperidyl) methylbutyric acid; (3F) 4- (4-methoxyphenyl) -4-oxo-3- (1-piperidyl) methylbutyric acid; (4F) 4-oxo-4-phenyl-3- (1-pyrrolidinyl) methylbutyric acid; (5F) 3- (4-morpholinyl) methyl-4-oxo-4-phenylbutyric acid; (6F) 3- {1- (4-methylpiperazinyl)} methyl-4-oxo-4-phenylbutyric acid; (7F) 3- (diethylamino) methyl-4-oxo-4-phenylbutyric acid; (8F) (1R, 2R) -3-oxo-2- (1-piperidyl) methyl-1-cyclopentanecarboxylic acid; (9F) 4-oxo-3- (1-piperidyl) methyl-4- (4-trifluoromethylphenyl) butyric acid; (10F) 4-oxo-3- (1-piperidyl) -4- (2-trifluoromethylphenyl) butyric acid; (11F) 4-oxo-3- (1-piperidyl) methyl-4- (3-trifluoromethylphenyl) butyric acid; (12F) 4-oxo-3- (1-piperidyl) methyl-4- (3-pyridyl) butyric acid; (13F) 4-oxo-3- (1-piperidyl) methyl-4- (2-pyridyl) butyric acid; (14F) 4-oxo-3- (1-piperidyl) methyl-4- (4-pyridyl) butyric acid; (15F) 3-oxo-2- (1-piperidyl) methyl-1-indanecarboxylic acid; (16F) 3-oxo-2- (1-pyrrolidinyl) methyl-1-indanecarboxylic acid; (17F) 2- (4-morpholinyl) methyl-3-oxo-1-indanecarboxylic acid; (18F) 2- {1- (4-methylpiperazinyl)} methyl-3-oxo-1-indanecarboxylic acid; (19F) 3- {1- (4-phenylpiperazinyl)} methyl-4-oxo-4-phenylbutyric acid; (20F) 4-oxo-4- (1-naphthyl) -3- (1-piperidyl) methylbutyric acid; (21F) 4-oxo-4- (2-naphthyl) -3- (1-piperidyl) methylbutyric acid; (22F) 4-oxo-4- (1-piperidyl) -3- (1-piperidyl) methylbutyric acid; (23F) 4-oxo-4- (4-methyl-1-piperazinyl) -3- (1-piperidyl) methylbutyric acid; (24F) 4-oxo-4- (4-phenyl-1-piperazinyl) -3- (1-piperidyl) methylbutyric acid; (25F) 4-oxo-4- (1-naphthyl) -3- (1-pyrrolidinyl) methylbutyric acid; (26F) 4-oxo-4- (2-naphthyl) -3- (1-pyrrolidinyl) methylbutyric acid; (26F) 4- (2-furyl) -4-oxo-3- (1-piperidyl) methylbutyric acid; (27F) 4- (3-furyl) -4-oxo-3- (1-piperidyl) methylbutyric acid; (28F) 4-oxo-3- (1-piperidyl) methyl-4- (2-thienyl) butyric acid; (29F) 4-oxo-3- (1-piperidyl) methyl-4- (3-thienyl) butyric acid; (30F) 4-oxo-3- (1-piperidyl) methyl-4- (2-pyrrolyl) butyric acid; (31F) 4-oxo-3- (1-piperidyl) methyl-4- (3-pyrrolyl) butyric acid; (32F) 4- (2-imidazolyl) -4-oxo-3- (1-piperidyl) methylbutyric acid; (33F) 4-oxo-4-phenyl-3- (1-piperidyl) methylbutyronitrile; (34F) methyl 4-oxo-4-phenyl-3- (1-piperidyl) methylbutyrate; (35F) ethyl 4-oxo-4-phenyl-3- (1-piperidyl) methylbutyrate; (36F) 4- (2-imidazolyl) -4-oxo-3- (1-pyrrolidinyl) methylbutyric acid; (37F) 4-oxo-4-phenyl-3- (1-pyrrolidinyl) methylbutyronitrile; (38F) 4-oxo-4-phenyl-3- (4-methyl-1-piperazinyl) methylbutyronitrile; (39F) 4-oxo-4-phenyl-3- (4-morpholinyl) methylbutyronitrile; (40F) 4- (2-imidazolyl) -4-oxo-3- (4-morpholinyl) methylbutyric acid; (41F) 2-methyl-4-oxo-4-phenyl-3- (1-piperazinyl) methylbutyric acid; (42F) 4- (1-piperazinyl) methyl-5-oxo-5-phenylpentanoic acid. The compounds of the present invention may exist in stereoisomeric forms such as geometric isomers and mixtures thereof, diastereoisomers and mixtures thereof, optical isomers and racemic isomers. Compounds of the present invention include all these stereoisomers and mixtures thereof. The compounds of the present invention may optionally be present in the form of their pharmacologically acceptable salts. Examples of these salts are salts with acids including inorganic salts such as hydrochlorides, sulfates, phosphates, salts of group IIIA (eg, aluminum salts), and salts with organic acids such as p-toluenesulfonate. Salts with bases include salts with alkali metals such as sodium and potassium, salts with alkaline earth metals such as calcium, and organic salts with methylamine and ethylenediamine. These pharmacologically acceptable salts of the present invention can be prepared by known methods. Hereinafter, a representative method for preparing the compounds of the present invention will be described, but the present invention is not limited to these methods. The compounds of the present invention and intermediates described below can be separated by conventional means such as extraction, recrystallization, chromatography and the like. [A] Method for Preparation of Compound of General Formula [1A] The compound of the general formula [1A], wherein X A is S, O, or NH is a cyclopentanone derivative represented by the following general formula [2A] (carbonyl group in one position may be protected as necessary; hereinafter simply a reactive derivative And (U is a leaving group and Z1 ' A , Z2' A and Z3 ' A have the same meaning as defined in Z1 A , Z2 A and Z3 A , but if these groups have functional groups, these groups may be optionally protected. ), A compound of the general formula [3A] below (Where X A 2 is S, O or NH and Y ' A has the same meaning as defined for Y A , but if this group has a functional group, this group may be protected as necessary) It can manufacture by removing a protecting group. Preferred examples of the above reactive derivatives are compounds of the general formulas [4A], [5A], [6A], [7A] and [8A] below. In the above structural formula, R15 is a hydrocarbon group having 1 to 10 carbon atoms, for example, an alkyl group, an alkenyl group or an aryl group. These groups may be substituted or unsubstituted. When the substituent (s) are functional groups, these groups may be protected with protecting groups as necessary. Each of R16 and R17 may be the same or different and is independently an alkyl group having 1 to 4 carbon atoms, or R16 and R17 are bonded together to form a piperazine ring or a pyrrolidine ring. Z1 ' A , Z2' A and Z3 ' A have the same meaning as defined above. Examples of compounds of the general formulas [4A], [5A], [6A] and [7A] are shown below. (a) 4-[(2,3-O-isopropylidene) propylsulfonyl] methyl-3-oxo-1-cyclopentanecarboxylic acid, (b) 4-methylidene-3-oxo-1-1-cyclopentanecarboxylic acid, (c) (2RS, 4S) -2-{(2R)-(2-acetylamino-2-methoxycarbonyl) ethylsulfonyl] methyl -4-hydroxycyclopentan-l-one. In the general formula [3A], wherein X A is S and Y A is an amino acid derivative residue, the compound of the general formula [3A] includes the following. (d) (2R) -2-acetylamino-2-carboxyethanethiol, (e) (2R) -2-acetylamino-2-methoxycarbonylethanethiol, For this reason, any condensation method may be used as long as the compound of the general formula [2A] can be condensed with the compound of the general formula [3A]. This reaction is carried out in an organic solvent, water or a mixture thereof. Organic solvents include aromatic hydrocarbons (e.g. benzene, toluene, etc.), alcohols (e.g. methanol, ethanol, etc.), ethers (e.g. tetrahydrofuran, diethyl ether, etc.), halogenated hydrocarbons (e.g. methylene chloride, chloroform, etc.), Ketones (eg acetone, methyl ethyl ketone, etc.), aprotic polar solvents (eg dimethyl sulfoxide, dimethylformamide, etc.) may be used. Examples of preferred solvents include ethers (e.g. tetrahydrofuran, diethyl ether), halogenated hydrocarbons (e.g. methylene chloride, chloroform), ketones (e.g. acetone, methyl ethyl ketone, etc.), aprotic polar solvents (e.g. dimethyl sulfoxide Seeds, dimethylformamide, etc.) or a mixture of this solvent and water. The reaction is generally preferably inorganic base such as potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate, sodium hydride, or triethylamine, 1,8-diazabicyclo [5.4.0] -undeca-7- Under basic conditions using an organic base such as Y, it is carried out in the absence of a catalyst or in the presence of an acid or a base. The use amount of these reactants is about 0.1 to 20 times mole, preferably about 0.5 to 5 times mole. Since the reaction temperature is not particularly limited, the reaction may be performed under cooling, or may be performed at room temperature or under heating. Preferably the reaction is carried out at a temperature between 0 ° C and 100 ° C. The compound of the formula [2A] is reacted with the compound of the formula [3A] in equimolar amounts. In practice, the compound of the general formula [3A] is used in an excess amount, such as an amount of 1 to 2 times molar. The reaction is carried out for 0.1 to 200 hours, preferably for 0.1 to 72 hours. The compound of the general formula [1A], wherein X A is SO 2 , can be prepared by oxidizing the compound of general formula [1A], wherein X A is S as an oxidizing agent. Examples of the oxidizing agent include organic peracids such as m-chloroperbenzoic acid, inorganic oxidizing agents such as permanganate, chromic acid and ruthenium tetraoxide, hydrogen peroxide and organic peroxide, and the like. Preferably, organic peracids such as m-chloroperbenzoic acid are used. . The compound of the general formula [1A] wherein X A is SO can be produced by oxidizing the compound of general formula [1A] wherein X A is S as an oxidizing agent. As the oxidizing agent, organic peroxides such as m-chloroperbenzoic acid, inorganic oxidizing agents such as manganese dioxide, chromic acid, ruthenium tetraoxide, and halogen-based oxidizing agents such as hydrogen peroxide, organic peroxide, and periodic acid are used. For example, the above compounds (a) and (b) are prepared by the following method. Starting material 2,4-bis (methoxycarbonyl) cyclopentanone (Compound 1A-A) is a known compound, which is described in J. Chem. Org. Chem., 47, 2379 (1982)] or a modification thereof can be prepared as a mixture of 2,3-bis (methoxycarbonyl) cyclopentanone (Compound 1A-a). After protecting the keto groups of the mixture (compounds 1A-B and 1A-b), the esters are reduced to convert to hydroxymethyl groups. The protecting group is then removed to give 2,4-bis (hydroxymethyl) cyclopentanone (Compound 1A-C) and 2,3-bis (hydroxymethyl) cyclopentanone (Compound 1A-c). Compound (1A-c) is removed by silica gel column chromatography to separate compound (1A-C). Compound (1A-C) is acylated by a conventional method to obtain compound (1A-D). The reaction for preparing compound (1A-E) from compound (1A-D) is carried out under conditions similar to those used for the condensation reaction between the compound of formula [2A] and the compound of formula [3A]. In this case, alpha-thioglycerine is used as a compound of general formula [3A]. Subsequently, the 1,2-diol group in the compound (1A-E) is protected, and as the protecting group, acetal, ketal or ortho-ester can be used. Compound (1A-E) is then converted to isopropylidene in the presence of an acid catalyst and acetone or an active derivative thereof to give compound (1A-F). Thereafter, compound (1A-G) is obtained by alkali hydrolysis of the compound (1A-F) by a conventional method to remove the acetyl group. The sulfide of the compound (1A-G) is then oxidized to obtain a sulfone. Thus, compound (1A-H) is obtained. This reaction is carried out under conditions similar to those used for the above-mentioned oxidation reaction, which is set up under conditions that do not oxidize the hydroxy group. In the case where the hydroxyl group is oxidized, the compound (a) is obtained. The hydroxy group is then oxidized to obtain compound (a). Examples of oxidizing agents that can be used are inorganic oxidizing agents such as permanganate and chromic acid, with chromic acid being preferred. Compound (b) is prepared by maintaining compound (a) under basic conditions similar to those used for the condensation reaction between a compound of formula [2A] and a compound of formula [3A]. It is not necessary to add the compound of general formula [3A] in this reaction. The reactants used in this reaction are inorganic bases such as potassium hydroxide, sodium hydroxide, potassium carbonate and sodium carbonate or organic bases such as triethylamine, 1,8-diazabicyclo [5.4.0] -undeca-7-ene, and the like. Although organic bases, such as triethylamine, are preferable. Compound (c) can be manufactured by the following method. Starting material (4R) -2- (N, N-diethylamino) methyl-4-tert-butyldimethylsiloxy-2-cyclopenten-l-one (Compound 3A-a) is a known compound and is commercially available. -Sold by Etsu Chemical. In the reaction for preparing compound (3A-b) from compound (3A-a), reaction conditions similar to those used for the condensation reaction between the compound of formula [2A] and the compound of formula [3A] are used. In this reaction, N-acetyl-L-cysteine is used as the compound of the general formula [3B]. The protecting group for the hydroxyl group of compound (3B-b) is removed by a conventional method using an acid or a fluorine compound. The sulfide of compound (3B-c) is then oxidized and converted to the corresponding sulfone to give compound (3B-d). This reaction can be carried out under conditions similar to those of the above-mentioned oxidation reaction that does not oxidize a hydroxy group. Subsequently, the double bond in the ring is reduced with a reducing agent to obtain compound (c). As the reducing agent, a contact reducing agent such as palladium-carbon, a soluble metal reducing agent such as lithium-ammonia, an organic hydride tin compound, or an organic hydrogenated silicon compound can be used, and preferably a contact reducing agent such as palladium-carbon. Compounds of the general formulas [4A] to [7A] other than the compounds (a) to (c) described above can be prepared by appropriately modifying the above-described methods used to prepare the compounds (a) to (c). Compound (c) is commercially available (Tokyo Kasei Corporation of Japan). Compound (e) can be easily prepared by heating compound (d) in methanol in the presence of an acidic catalyst. Examples of the acidic catalyst include organic acids such as hydrochloric acid and sulfuric acid, organic acids such as p-toluenesulfonic acid, and Lewis acids such as boron fluoride etherate. Organic acids such as p-toluenesulfonic acid are preferable. For example, compound (4A) of the present invention can be readily prepared by amidation of compound (3A) as shown below. This amidation is carried out under basic conditions or using a condensing agent. It is preferable to use a condensing agent for this amidation. Examples of the condensing agent include dicyclocarbodiimide (DCC) and WSC. Compounds (5A) and (6A) of the present invention can be produced by heating and reacting a compound of the general formula [8a] with a compound of the general formula [3A]. The desired product is obtained by heating the reaction to 30 ° C to 200 ° C in the absence of a solvent or in the presence of an organic solvent. As a compound of general formula [8A], (f) 2- (1-piperidylmethyl) -3-oxo-1- indancarboxylic acid is typical, for example. The compound (f) is described in J. Med. Chem., 7, 716, (1964)]. [B] Method for Preparation of Compound of General Formula [1B] The compound of the general formula [1B] wherein X B is S, O or NH is a 2,3-substituted cyclopentanone derivative represented by the following general formula [2B] (carbonyl group in one position may be appropriately protected; Simply referred to as reactive derivatives), (In the above formula, U is a leaving group and Z ' B has the same meaning as Z B , but if this substituent has a functional group, this functional group may be appropriately protected.) Compound of the general formula [3B] below (Where X B 2 is S, O or NH, and Y ' B has the same meaning as defined for Y B , but this may adequately protect the functional group) and then if necessary, by removing the protecting group It can manufacture. Preferred examples of the reactive derivatives described above are compounds of the following general formulas [4B], [5B], [6B] and [7B]. In the above formulas, R18 is an aliphatic group or an aryl group having 1 to 10 carbon atoms such as an alkyl group or an alkenyl group. These groups may be substituted or unsubstituted. When the functional group (s) have a substituent, these functional groups may be appropriately protected with a protecting group. Examples of the compounds of the general formulas [4B], [5B], [6B] and [7B] are as follows. (a) 2,3-bis (acetoxymethyl) cyclopentanone (b) 3-acetoxymethyl-2-methylidenecyclopentanone (c) 2-[(2,3-O-isopropylidene) propylsulfonyl] methyl-3-oxo-1-cyclopentanecarboxylic acid (d) 2-[(2,3-O-isopropylidene) propylsulfonyl] methyl-3-methoxycarbonylcyclopentanone (e) 2-methylidene-3-oxo-1-cyclopentanecarboxylic acid (f) 3-methoxycarbonyl-2-methylidenecyclopentanone In the general formula [3B], wherein X B is S and Y B is an amino acid derivative residue, the compound of the general formula [3B] includes the followings. (g) (2R) -2-acetylamino-3-oxo-3- (1-pyrrolidinyl) propanethiol (h) (2R) -2-acetylamino-3- (4-morpholinyl) -3-oxo-propanethiol (i) (2R) -2-acetylamino-3-oxo-3- (1-piperidyl) propanethiol (j) (2R) -2-acetylamino-3-oxo-3- (1-pyrrolidinyl) propanethiol (k) (2R) -2-acetylamino-3- [1-{(2S) -2-methoxycarbonyl} pyrrolidinyl) -3-oxopropanethiol (l) (2R) -2-acetylamino-3- [1-{(2S) -2-methoxycarbonyl} azetidinyl) -3-oxopropanethiol (m) (2R) -2-acetylamino-3-oxo-3- (1-piperazinyl) propanethiol (n) (2R) -2-acetylamino-3- {1- (4-hydroxymethyl) piperazinyl} -3-oxopropanethiol (o) (2R) -2-acetylamino-3- {1- (4-tert-butoxycarbonyl} piperazinyl) -3-oxopropanethiol (p) (2R) -2-acetylamino-3- {1- (4-phenyl) piperazinyl} -3-oxopropanethiol (q) (2R) -2-carboxy-2-pentafluoropropionyl-aminoethanethiol (r) 1-acetylamino-1-carboxy-11-mercaptodecanthiol (s) 2-acetylamino-2- (5-tetrazolyl) ethanethiol (t) 3- (3-pyridyl) propanethiol (u) 3- {3- (1-methylpyridinium iodide)} propanethiol As long as the compound of the formula [2B] can be condensed with the compound of the formula [3B], the above reaction can be carried out through any condensation reaction. This reaction is generally carried out in organic solvents, water or mixtures thereof. Organic solvents include aromatic hydrocarbons (e.g. benzene, toluene, etc.), alcohols (e.g. methanol, ethanol, etc.), ethers (e.g. tetrahydrofuran, diethyl ether, etc.), halogenated hydrocarbons (e.g. methylene chloride, chloroform, etc.), Ketones (eg acetone, methyl ethyl ketone, etc.), aprotic polar solvents (eg dimethyl sulfoxide, dimethylformamide, etc.) may be used. Examples of preferred solvents include ethers (e.g. tetrahydrofuran, diethyl ether), halogenated hydrocarbons (e.g. methylene chloride, chloroform), ketones (e.g. acetone, methyl ethyl ketone, etc.), aprotic polar solvents (e.g. dimethyl sulfoxide Seeds, dimethylformamide, etc.) or a mixture of this solvent and water. The reaction is preferably carried out, generally under basic conditions, in the absence of a catalyst or in the presence of an acid or a base. The reactants used in this reaction are inorganic bases such as potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate and sodium hydride, or triethylamine, 1,8-diazabicyclo [5.4.0] -undeca-7-ene Organic bases; The use amount of these reactants is about 0.1 to 20 times mole, preferably about 0.5 to 5 times mole. Since the reaction temperature is not particularly limited, the reaction may be performed under cooling, or may be performed at room temperature or under heating. Preferably the reaction is carried out at a temperature between 0 ° C and 100 ° C. The compound of the formula [2B] is reacted with the compound of the formula [3B] in equimolar amounts. In practice, the compound of the general formula [3B] is used in an amount of excess, such as 1 to 2 moles. The reaction is carried out for 0.1 to 200 hours, preferably for 0.1 to 72 hours. The compound of the general formula [1B], wherein X B is SO 2 , can be produced by oxidizing the compound of the general formula [1B], wherein X B is S. Examples of the oxidizing agent include organic peracids such as m-chloroperbenzoic acid, inorganic oxidizing agents such as permanganate, chromic acid and ruthenium tetraoxide, hydrogen peroxide and organic peroxide, and the like. Preferably, organic peracids such as m-chloroperbenzoic acid are used. . The compound of the general formula [1B], wherein X B is SO, can be produced by oxidizing the compound of general formula [1B], wherein X B is S as an oxidizing agent. As the oxidizing agent, organic peroxides such as m-chloroperbenzoic acid, inorganic oxidizing agents such as manganese dioxide, chromic acid, ruthenium tetraoxide, and halogen-based oxidizing agents such as hydrogen peroxide, organic peroxide, and periodic acid are used. For example, the above compounds (a) and (b) are prepared by the following method. Starting material 2,3-bis (hydroxy groupmethyl) cyclopentanone (Compound a-1) is a compound known in the literature, for example, prepared by the method described in JP-A-5-1044 or a modification thereof. can do. Compound (a) is obtained by acetylating compound a-1 in a conventional manner. Compound (a) which is optically active and has a stereoconfiguration of (2R, 3S) can also be produced by the method disclosed in Japanese Patent Application Laid-open No. Hei 8-231469. The compound (a) of the optically active type can be prepared by optically dividing the optically inactive type, for example, by chromatography for optical separation. Compound (b) can be prepared by maintaining compound (a) under conditions similar to those used for the condensation reaction between the compound of the formula [2B] and the compound of the formula [3B]. In carrying out this reaction, it is not necessary to add the compound of general formula [3B]. The reactants used in this reaction are inorganic bases such as potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate, sodium hydride or triethylamine, 1,8-diazabicyclo [5.4.0] -undeca-7-ene, and the like. Although it is an organic base of, organic bases, such as triethylamine, are preferable. Compounds (c) and (d) can be produced by the following method. The reaction for preparing the compound (a-2) from the compound (a) is carried out under conditions similar to those used in the condensation reaction between the compound of the formula [2B] and the compound of the formula [3B]. In this case, alpha-thioglycerine is used as a compound of general formula [3B]. As the protecting group, acetal, ketal or ortho-ester is used. Subsequently, compound (a-2) is converted to isopropylidene in the presence of an acid catalyst and acetone or an activated derivative thereof to obtain compound (a-3). Thereafter, compound (a-4) is obtained by alkali hydrolysis of the compound (a-3) in a conventional manner to remove the acetyl group. Next, compound (a-5) is manufactured by oxidizing the sulfide of compound (a-4) to sulfone. This reaction is carried out under the conditions used for the above-mentioned oxidation reaction which does not oxidize the hydroxyl group. When the hydroxy group is oxidized, compound (a) is obtained. The hydroxyl group is then oxidized to yield compound (c). Examples of the oxidizing agent that can be used in this reaction are inorganic oxidizing agents such as permanganate and chromic acid, preferably chromic acid. Finally, the carboxylic acid of compound (c) is esterified by a conventional method to obtain compound (d). Compounds (e) and (f) can be prepared from compounds (c) and (d) under conditions similar to those used to convert compound (a) to compound (b). The optically active forms (compounds C and D) of compounds (c) and (d) are prepared in a similar manner to the preparation of compounds (c) and (d) as described below. Compounds of the general formulas [4B] to [7B] other than the above-mentioned compounds (a) and (f) can be manufactured by suitably modifying the above-mentioned method used when manufacturing compounds (a) and (f). Compounds (g) and (u) can be produced as follows. Compound (g-2) is prepared by benzoylation of N-acetyl-L-cysteine (g-1) in a conventional manner. Subsequently, the compound of the following general formula [8b] is reacted with amide formation by a conventional method. Wherein W4 is 1-piperidyl, 1-pyrrolidinyl, 4-morpholinyl, 1- (2-methoxycarbonyl) azetidinyl, 1- (2-methoxycarbonyl) pyrroli Diyl, 1-piperazinyl, 1- (4-hydroxyethyl) piperazinyl, 4-phenylpiperazinyl or 1- (4-tert-butoxycarbonyl) piperazinyl.) Thus, compound (g-3) is prepared. Compound (g)-(p) are obtained by hydrolyzing and removing the benzoyl group which is a protecting group. Compound (q) can be easily prepared by reacting L-cysteine with pentafluoropropionic anhydride. Compound (r) is prepared as shown below. Compound (r-2) is prepared by reacting a readily available compound (r-1) with diethyl acetylaminomalonate in the presence of a base, which is a common method for preparing amino acid derivatives. Subsequently, compound (r-2) is converted into compound (r-3) by removing the benzoyl group which is a protecting group by a conventional method. Compound (r-4) is prepared by heating and decarbonizing compound (r-3) under acidic conditions. After protecting the carboxyl group into methyl ester form, 2-fluoro-1-methylpyridinium p-toluenesulfonate, thioacetic acid and triethylamine were used as reactants, and hydroxy groups were converted under mild conditions by conventional methods. Let it be acetylthio group. Thus, compound (r-5) is prepared. Compound (r) is obtained from compound (r-5) by removing the methoxy group and the S-acetyl protecting group under mild basic conditions. Compound (s) is readily prepared by converting COOH of L-cysteine protected thiol group to cyano group, and then reacting with sodium azide to convert 5-tetrazolyl group, then removing protecting group to liberate thiol can do. Compound (t) can be easily produced by the method described in Chemistry Letters, 133-136 (1977), using 3-pyridinepropanol as the starting compound. Compound (u) can be easily prepared by reacting compound (t) in which a thiol group is protected with methyl iodide and then removing the protecting group from the obtained pyridinium iodide. [C] Method of Preparation of Compound of General Formula [1C] The compound of the general formula [1C], wherein X C is S, O or NH, represents a cyclopentanone derivative represented by the following general formula [2C]. (U is a leaving group and Z1 ' C , Z2' C and Z3 ' C have the same meaning as defined in Z1 C , Z2 C and Z3 C , but when this group contains a functional group, May be suitably protected), and reacted with a compound of the following general formula [3C], (In the above formula, X C 2 is S, O or NH, and Y ' C has the same meaning as defined in Y C. However, if this group contains a functional group, it may be appropriately protected.) If necessary, it can manufacture by removing a protecting group. Preferred examples of the reactive derivatives described above are compounds of the following general formulas [4C], [5C], [6C], [7C] and [8C]. In the above formulas, R 16 is an aliphatic hydrocarbon group having 1 to 10 carbon atoms, such as an alkyl group, an alkenyl group or an aryl group. These groups may be substituted or unsubstituted. When the substituent (s) are functional group (s), these functional groups may be protected with a protecting group when necessary. R17 and R18 are each hydrogen or an aliphatic hydrocarbon group having 1 to 10 carbon atoms, such as an alkyl group, an alkenyl group or an aryl group. These groups may be substituted or unsubstituted. When the substituent (s) are functional group (s), these functional groups may be protected with a protecting group when necessary. Z1 ' C , Z2' C and Z3 ' C have the same meaning as defined above. Examples of compounds of the general formulas [4C], [5C], [6C], [7C] and [8C] are as follows. (a) 2-[(2R)-(2-acetylamino-2-methoxycarbonyl) ethylsulfonyl] methyl-4-tert-butyldimethylsiloxy-2-cyclopentan-1-one (b) 2-methylidene-4-tert-butyldimethylsiloxy-2-cyclopentan-1-one (c) 2-diethylaminomethyl-4-tert-butyldimethylsiloxy-2-cyclopenten-l-one (d) 3-acetoxy-2-benzenesulfonylmethyl-2-cyclopenten-l-one Compounds of the general formula [3C] wherein X C is S include the following. (e) (2R) -2-acetylamino-2-carboxyethanethiol (f) (2R) -2-acetylamino-2-methoxycarbonylethanethiol In order to carry out the reaction, any condensation reaction can be used as long as the compound of the formula [2C] can be condensed with the compound of the formula [3C]. This reaction is generally carried out in organic solvents, water or mixtures thereof. Organic solvents include aromatic hydrocarbons (e.g. benzene, toluene, etc.), alcohols (e.g. methanol, ethanol, etc.), ethers (e.g. tetrahydrofuran, diethyl ether, etc.), halogenated hydrocarbons (e.g. methylene chloride, chloroform, etc.), Ketones (eg acetone, methyl ethyl ketone, etc.), aprotic polar solvents (eg dimethyl sulfoxide, dimethylformamide, etc.) may be used. Examples of preferred solvents include ethers (e.g. tetrahydrofuran, diethyl ether), halogenated hydrocarbons (e.g. methylene chloride, chloroform), ketones (e.g. acetone, methyl ethyl ketone, etc.), aprotic polar solvents (e.g. dimethyl sulfoxide Seeds, dimethylformamide, etc.) or a mixture of this solvent and water. The reaction is preferably, in general, inorganic bases such as potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate, sodium hydride, or triethylamine, 1,8-diazabicyclo [5.4.0] -undeca-7 It proceeds in basic condition, in absence of a catalyst, or in presence of an acid or a base using organic base, such as -ene. The use amount of these reactants is about 0.1 to 20 times mole, preferably about 0.5 to 5 times mole. Since the reaction temperature is not particularly limited, the reaction may be performed under cooling, or may be performed at room temperature or under heating. Preferably the reaction is carried out at a temperature between 0 ° C and 100 ° C. The compound of the formula [2C] is reacted with the compound of the formula [3C] in equimolar amounts. In practice, the compound of the general formula [3C] is used in an amount of excess, such as 1 to 2 moles. The reaction is carried out for 0.1 to 200 hours, preferably for 0.1 to 72 hours. When compound (a) or compound (b) is selected as a compound of the general formula [2C], the desired cyclopentenone derivative is obtained by further dehydration after removing the protecting group of the hydroxy group from the obtained condensation reaction product. As reactants for protecting group removal and dehydration, acids, acidic resins, Lewis acids or fluoride reagents are used. Acids that can be used include inorganic acids such as hydrochloric acid and sulfuric acid and organic acids such as p-toluenesulfonic acid and acetic acid. As acidic resin, Dowex 50 is preferable. Boron fluoride etherate and the like can be advantageously used as Lewis acid. Fluorine reagents include tetrabutylammonium fluoride and hydrogen fluoride. In the compound of the formula [2C], wherein X C is N, when the compound of the formula [7C] is condensed with the compound of the formula [3C], the desired condensation reaction product is nitrogen of the compound of the formula [7C]. Methylated or oxidized, and then the methylated or oxidized product is reacted with a compound of the general formula [3C]. Examples of methylating agents are methyl halide or dimethyl sulfate, with methyl iodide being preferred. Examples of the oxidizing agent include organic peroxides such as m-chloroperbenzoic acid, hydrogen peroxide and organic peroxides. Organic peracids or hydrogen peroxide such as m-chloroperbenzoic acid are preferred. X C is SO 2 A compound of general formula [1C] is, X is C may be prepared by oxidizing the compounds of the S general formula [1C]. Suitable oxidizing agents include organic peracids such as m-chloroperbenzoic acid, inorganic oxidizers such as manganese dioxide, chromic acid and ruthenium tetraoxide, hydrogen peroxide and organic peroxides, with organic peracids such as m-chloroperbenzoic acid being preferred. . Compound of general formula [1C] whose X C is SO can be manufactured by oxidizing the compound of general formula [1C] whose X C is S. Oxidants suitable for use include organic peracids such as m-chloroperbenzoic acid, inorganic oxidizers such as manganese dioxide, chromic acid, ruthenium tetraoxide, and halogen-based oxidizers such as hydrogen peroxide, organic peroxides, and periodic acid. For example, said compound (a) and compound (b) can be manufactured as follows. The starting compound (c) is known and commercially available from Nissan Chemical Corporation of Japan. Compound (c) may be converted to compound (a-1) under reaction conditions similar to those used for the condensation reaction of the compound of formula [2C], wherein X C is N. Subsequently, the compound (a-2) may be prepared under similar reaction conditions as the oxidation to SO 2 described above. The carbon-carbon double bond of compound (a-2) is reduced by a conventional method to obtain compound (a). As the reducing agent, an alkali metal reducing agent, an organotin reducing agent, an organic silicon reducing agent, a reducing agent for catalytic hydrogenation, and the like can be used. A reducing agent for catalytic hydrogenation such as palladium-carbon is preferable. Compound (b) can be prepared by keeping compound (a) under basic conditions. Reactants that can be used in basic conditions include inorganic bases such as potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate and sodium hydride, and triethylamine, 1,8-diazabicyclo [5.4.0] -undeca-7- Although it is organic bases, such as ene, organic bases, such as a triethylamine and 1,8- diazabicyclo [5.4.0] -undeca-7-ene, are preferable. Compound (d-1) is a compound known in the literature and described in J. Org. Chem., 58, 3953 to 3959 (1993)]. You may manufacture compound (d) by acetylating compound (d-1) by a conventional method. In addition to the compounds (a) to (d), the compounds of the general formulas [4C] to [8C] can be produced by suitably modifying the methods for producing the compounds (a) to (d). Compound (e) is commercially available (Tokyo Kasei Co., Ltd., Japan). Compound (f) can be easily prepared by heating compound (e) in methanol in the presence of an acidic catalyst. Examples of the acidic catalyst include inorganic acids such as hydrochloric acid and sulfuric acid, organic acids such as p-toluenesulfonic acid, and Lewis acids such as boron fluoride etherate. Organic acids such as p-toluenesulfonic acid are preferable. [D] Method for Preparation of Compound of General Formula [1D] The compound of the general formula [1D], wherein X D is S, O, or NH, may be a ketone derivative represented by the following general formula [2D], which may suitably protect a carbonyl group in one position; hereinafter simply referred to as a reactive derivative. (In the above formula, U is a group to be separated and removed, and A ' D , B' D and Z ' D have the same meaning as defined in A D , B D and Z D , but when this group contains a functional group, this functional group May be properly protected) React with a compound of the following general formula [3D], (In the above formula, X D 2 is S, O or NH, and Y ' D has the same meaning as defined for Y D , but if this group contains a functional group, it may be appropriately protected.) If necessary, it is prepared by removing the protecting group. Preferred examples of the above reactive derivatives are compounds of the following general formulas [4D], [5D], [6D], [7D] and [8D]. In the above formulas, R16 is an aliphatic group having 1 to 10 carbon atoms, for example, an alkyl group, an alkenyl group, or an aryl group. These groups may be substituted or unsubstituted. When the substituent (s) are functional group (s), these functional groups may be appropriately protected with a protecting group. R17 and R18 may be the same or different, and each independently represent an alkyl group having 1 to 4 carbon atoms, or R17 and R18 combine together to form a piperazine ring or a pyrrolidine ring. A ' D , B' D and Z ' D have the same meaning as defined above. R16 and Z ' D are also bonded together to form a γ-butyrolactone ring. Examples of the compounds of the general formulas [4D], [5D], [6D], [7D], and [8D] are as follows. (a) 4-acetyl-γ-butyrolactone (b) 3-methylidene-4-oxo-1-n-pentanoic acid (c) trans-2,3-bis (acetoxymethyl) -1-cyclobutanone (d) 3-acetoxymethyl-2-methylidene-1-cyclobutanone (e) 3-ethoxycarbonyl-2-methanesulfoxymethyl-1-cyclobutanone (f) 3-ethoxycarbonyl-2-methylidene-1-cyclobutanone (g) 2-[(2,3-O-isopropylidene) propylsulfonyl] -methyl-3-oxo-1-cyclohexanecarboxylic acid (h) 2-methylidene-3-oxo-1-cyclohexanecarboxylic acid (i) 4-oxo-4-phenyl-3- (1-piperidyl) methylbutyric acid (j) 4-oxo-4- (3-pyridyl) -3- (1-piperidyl) methylbutyric acid (p) 4- (1-piperidyl) methyl-5-oxo-5-phenylpentanoic acid Compounds of the general formula [3D], wherein X D is S, include the following compounds. (q) (2R) -2-acetylamino-2-carboxyethanethiol (r) (2R) -2-acetylamino-2-methoxycarbonylethanethiol (s) 2,3-dihydroxypropane-1-thiol (alpha-thioglycerine) In order to carry out the reaction, any condensation method can be used as long as the compound of the formula [2D] can be condensed with the compound of the formula [3D]. This reaction is generally carried out in organic solvents, water or mixtures thereof. Organic solvents include aromatic hydrocarbons (e.g. benzene, toluene, etc.), alcohols (e.g. methanol, ethanol, etc.), ethers (e.g. tetrahydrofuran, diethyl ether, etc.), halogenated hydrocarbons (e.g. methylene chloride, chloroform, etc.), Ketones (eg acetone, methyl ethyl ketone, etc.), aprotic polar solvents (eg dimethyl sulfoxide, dimethylformamide, etc.) may be used. Examples of preferred solvents for use include ethers (e.g. tetrahydrofuran, diethyl ether), halogenated hydrocarbons (e.g. methylene chloride, chloroform), ketones (e.g. acetone, methyl ethyl ketone, etc.), aprotic polar solvents (e.g. : Dimethyl sulfoxide, dimethylformamide, etc.), alcohol (for example, methanol, ethanol, etc.), or a mixture of this solvent and water. The reaction is preferably carried out, generally under basic conditions, in the absence of a catalyst or in the presence of an acid or a base. When the catalyst is not used, the reaction may sometimes proceed by heating. The reactants used to maintain the reaction system are inorganic bases such as potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate and sodium hydride, or triethylamine, 1,8-diazabicyclo [5.4.0] -undeca-7 -An organic base such as yen. The use amount of these reactants is about 0.1 to 20 times mole, preferably about 0.5 to 5 times mole. Since the reaction temperature is not particularly limited, the reaction may be performed under cooling, or may be performed at room temperature or under heating. Preferably the reaction is carried out at a temperature between -20 ° C and 130 ° C. As for the temperature in the case of performing a condensation reaction in the absence of a catalyst, 30 degreeC-200 degreeC is preferable. The compound of the formula [2D] is reacted with the compound of the formula [3D] in equimolar amounts. In practice, the compound of the general formula [3D] is used in an excess amount, such as in an amount of 1 to 2 times molar. The reaction is carried out for 0.1 to 200 hours, preferably for 0.1 to 72 hours. The compound of the general formula [1D], wherein X D is SO 2 , can be produced by oxidizing the compound of the general formula [1D], wherein X D is S. Suitable oxidizing agents include organic peracids such as m-chloroperbenzoic acid, inorganic oxidizers such as permanganate, chromic acid and ruthenium tetraoxide, hydrogen peroxide and organic peroxides, with organic peracids such as m-chloroperbenzoic acid being preferred. . The compound of the general formula [1D], wherein X D is SO, can be produced by oxidizing the compound of the general formula [1D], wherein X D is S. Oxidants suitable for use include organic peracids such as m-chloroperbenzoic acid, inorganic oxidizers such as manganese dioxide, chromic acid, ruthenium tetraoxide, and halogen-based oxidizers such as hydrogen peroxide, organic peroxides, and periodic acid. For example, the compound (a) and the compound (b) can be prepared as follows. Compound (a) is known, for example Bull. Chem. Soc. It can be manufactured by the method described in Jpn., 32, 1282 (1959). Compound (b) is also known and can be produced, for example, by the method disclosed in Japanese Patent Application Laid-open No. 37-5911. Compound (b) can be prepared by maintaining compound (a) under acidic or basic conditions. The reactants used in the reaction include inorganic bases such as potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate and sodium hydride, and triethylamine, 1,8-diazabicyclo [5.4.0] -undeca-7-ene Although it is organic bases, such as these, organic bases, such as triethylamine and 1,8- diazabicyclo [5.4.0] -undeca-7-ene, or inorganic acids, such as a sulfuric acid, are preferable. Compound (c) and compound (d) can be prepared as follows. Compound (c) is known and can be prepared, for example, by the method described in Tetrahedron Lett., 6453 (1989), and compound (c) itself can be readily prepared by the method described herein. Compound (d) can be prepared by keeping compound (c) under basic conditions. The reactants advantageously used in this reaction include inorganic bases such as potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate, sodium hydride, and triethylamine, 1,8-diazabicyclo [5.4.0] -undeca-7 Although it is organic bases, such as -ene, organic bases, such as triethylamine and 1,8- diazabicyclo [5.4.0] -undeca-7-ene, are preferable. Compound (e) and compound (f) can be manufactured as follows. Compound (e-1) is known, such as J. Org. It can be prepared by the method described in Chem., 53, 3841 (1989). To convert compound (e-1) to compound (e) and then to compound (f), J. Org. The method described in Chem., 53, 611 (1988) is suitably modified and applied. That is, compound (e-2) can be manufactured by treating compound (e-1) with a base and treating the produced anion with formaldehyde. LDA, n-butyllithium, KHMDS, sodium hydride, etc. can be used as a base, but LDA is preferable. Formaldehyde is preferably reacted with a monomer after cracking the polymer. Compound (e) can be manufactured by mesylating compound (e-2) by a conventional method. More specifically, compound (e-2) is reacted with mesyl chloride and ice-cooling in the presence of triethylamine which is a base in methylene chloride. Subsequently, compound (f) is simultaneously produced via compound (e) in the same system. Compound (g) and compound (h) can be manufactured as follows. Compound (g-1) and compound (g-2) known and commercially available in the literature are subjected to a Diels-Alder reaction in a conventional manner to obtain compound (g-3). Compound (g-3) is reduced with lithium aluminum hydride to convert to compound (g-4) to remove the silyl group, which is a protecting group. The allyl alcohol component in compound (g-4) is oxidized to manganese dioxide in a conventional manner. After the hydroxy group of the obtained compound (g-5) is acetylated in acetic anhydride-pyridine as a reactant, palladium-carbon is used to reduce the double bond in the ring. In this way, compound (g-6) can be obtained easily. Compound (g-7) is obtained by reacting compound (g-6) under conditions similar to those used when condensing compound (2D) and compound (3D). In this reaction, alpha-thioglycerine is used as the compound of the general formula [3D]. The 1,2-diol group of compound (g-7) is then protected with a protecting group such as acetal, ketal or ortho-ester. Preferably, compound (g-7) is reacted with acetone or an active derivative thereof in the presence of an acid catalyst to obtain compound (g-8), in which case 1,2-diol is protected with isopropylidene. Subsequently, the acetyl group is removed by alkaline hydrolysis in a conventional manner to obtain compound (g-9). The sulfide of compound (g-9) is oxidized to obtain sulfone. Thus, compound (g-10) is obtained. This reaction is carried out under conditions similar to those used for oxidation which does not oxidize hydroxy groups. When the hydroxyl group is oxidized to COOH, compound (g) can be obtained in one step. Compound (g) can be prepared by oxidizing a hydroxy group with an oxidizing agent. Examples of the oxidizing agent that can be used include inorganic acids such as permanganate and chromic acid, and chromic acid is preferable. Compound (h) can be prepared by maintaining compound (g) under basic conditions similar to those used when condensing compound [2D] and compound [3D] without adding compound [3D] to the reaction system. The reactants which can be advantageously used for this reaction include inorganic bases such as potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate, triethylamine, 1,8-diazabicyclo [5.4.0] -undeca-7-ene, and the like. Although it is an organic base of, organic bases, such as triethylamine, are preferable. Compound (i) is known and is described, for example, in J. Chem. Soc. (C), 2308 (1967). Compound (j) reacts acrylic acid with a corresponding aldehyde in the presence of sodium cyanide or 3-benzyl-5- (2-hydroxyethyl) -4-methylthiazolium chloride as a catalyst [Chem. Ber., 109, 289, 541 (1976) and then the reaction product can be prepared by Mannich reaction. Compound (p) can be manufactured by making it react with well-known 5-oxo-5-phenylpentanoic acid. Compounds (q) and (s) are commercially available from Tokyo Kasei. Compound (r) can be easily prepared by heating compound (q) in methanol in the presence of an acid catalyst. Examples of the acidic catalyst include inorganic acids such as hydrochloric acid and sulfuric acid, organic acids such as p-toluenesulfonic acid, and Lewis acids such as boron fluoride etherate, and organic acids such as p-toluenesulfonic acid are preferable. [E] Preparation of Compound of General Formula [1E] The compound of the general formula [1E] (hereinafter sometimes referred to as the bioactive substance NA) is cultured with the NA 32176 acid strain belonging to the genus Streptomyces® to produce and accumulate the bioactive substance NA32176A. The bioactive substance NA32176A can be collected from the culture solution. Representative bacteria that can produce the bioactive substance NA32176A have the following microbiological and physiological properties. 1. Morphological Properties When observed after 2 weeks of incubation at 27 ° C., they simply branched into aerial mycelia, and the upper part is spiral or hook shaped. No spore sac or leap bifurcation is observed, and no zoospore is observed. Spore surface is flat or rough. Spores are cylindrical and have a size of 0.7 to 0.9 x 1.3 μm. Spores are formed in more than 20 chains. 2. Growth in various media Growth conditions for 2 weeks at 27 ° C. in various media are shown in Table 1 below. TABLE 1 badge Growth Aerobic Mycelium Substrate mycelium Soluble pigment Sucrose-nitrate agar medium Gentle Mild, white to light brown to black (hygroscopic) Colorless to pale yellow none Lucose-Asparagine-Agar Badge Gentle Rich, brownish white ~ light brown ~ black (hygroscopic) Pale yellow to brown Light brown Glucose-asparagine-agar medium (ISP 5 med.) Gentle Rich, brownish white ~ light brown ~ black (hygroscopic) Colorless to pale yellow Brown Starch-Inorganic Salt-Agar Medium (ISP 4 med.) Good Mild, brownish white ~ light brown ~ black (hygroscopic) buff Light brown Tyrosine-agar medium (ISP 7 med.) Good Mild, brownish white ~ light brown ~ black (hygroscopic) buff Brown Nutrients-Agar Medium Good Gentle, white buff Light brown Yeast-maltose-agar medium (ISP 2 med.) Good Rich, brownish white-light brown to black (hygroscopic) Colorless Light brown Oatmeal-Agar Medium (ISP 3 med.) Gentle Mild, brownish white ~ light brown ~ black (hygroscopic) Colorless none 3. Physiological Properties 1) Optimum growth temperature range: 24 ~ 37 ℃ 2) reduction of nitrate: negative 3) Liquefaction of gelatin (glucose-peptone-gelatin medium, 20 ° C.): pseudopositive 4) Hydrolysis of Starch (Starch-Inorganic Salt-Agar Medium): Positive 5) Solidification of skim milk: negative 6) Peptonation of skim milk: positive 7) Melanin Pigment Generation: Negative 4. Assimilation of carbon sources (Pridham-Gottlieb agar medium) L-Arabinose + D-xylose + D-glucose + D-fructose + Sucrose + Inositol- L-Rhamnose- Raffinose + D-mannitol + 5. Diaminopimelic Acid in the Cell Wall LL-diaminopimelic acid From the results above, the cell wall of this strain is LL-diaminopimelic acid, and according to the International Streptomyces Project (ISP), the form of spore-forming mycelium belongs to the section spiral. Spore surface is flat or rough; This mycelium is grayish and hygroscopic. No melanin-like pigments are produced. Substrate mycelium is light yellow or light brown. This strain assimilates L-arabinose, D-glucose, D-fructose, sucrose, raffinose, D-rhamnose, D-mannitol and D-xylose as carbon sources. Based on the above properties, R.E.Buchanan & N.E. Gibbons, Bergey's Manual of Determinative Bacteriology, 8th edition, 1974], strain NA32176 was found to belong to the genus Streptomyces. It was named NA32176. The strain was deposited and deposited with the National Institute Bioscience and Human-Technology Agency of Industrial Science and Technology (No. 1 to 3, Higashi 1-chome, Tsukubashi, Ibaraki, JAPAN) on August 8, 1997. It was assigned No. FERM P-16372. This deposit was subsequently converted to an international deposit by the Budapest Treaty on 7 July 1998 and was given accession number FERM BP-6411. This strain with acid production of the physiologically active substance NA32176A of the present invention having the above-mentioned nerve cell differentiation promoting action belongs to the genus Streptomyces. Streptomyces sp. Isolated by the present inventors NA32176 (Accession No. FERM P-16372 from the National Institute Bioscience and Human-Technology Agency of Industrial Science and Technology; International Accession No. FERM BP-6411) is one of the strains most effectively used in the present invention. Strains belonging to the genus Streptomyces used in the present invention, like other strains belonging to the genus Streptomyces, since their properties are easily changed, for example, easily mutated by artificial mutations using UV rays, X-rays or chemicals, etc. . Any mutant can be used in the present invention as long as the bioactive substance NA32176A has an acid capacity of the present invention. To prepare the bioactive substance NA32176A according to the present invention, the above-mentioned strain is cultured aerobicly in a medium containing nutrients capable of assimilating Streptomyces. As a nutrient source, you may use the well-known nutrient conventionally used for culturing Streptomyces. As a carbon source, glucose, fructose, glycerin, sucrose, dextrin, galactose, organic acids, etc. can be used individually or in combination. Inorganic materials such as ammonium chloride, ammonium sulfate, urea, ammonium nitrate, sodium nitrate, peptone, hex, yeast extract, dry yeast, corn steep liquor, soy flour, cottonseed leek, casamino acid, bactosodium, soluble vegetable protein, oatmeal Or organic nitrogen sources may be used alone or in combination. If necessary, inorganic salts such as sodium chloride, calcium carbonate, magnesium sulfate, copper sulfate, zinc sulfate, iron sulfate, magnesium chloride, and phosphate may be added to the system to supplement. Furthermore, organic substances and inorganic substances such as amino acids, vitamins, nucleic acids and the like can also be appropriately added to the culture system to supplement them. Liquid culture, especially deep spinner culture, is most suitable for the culture. It is preferable to incubate at a temperature of 20 ° C to 40 ° C in a slightly acidic to slightly alkaline pH range. In the case of liquid medium, incubation for 2 to 5 days generally produces and accumulates the bioactive substance NA32176A in the culture juice. When the production amount of this substance reaches the maximum, the culture is terminated. Cells are then separated from the medium by filtration and the product is purified by separation. The purification and separation of the product from the filtrate can be carried out by a method conventionally applied to the purification and separation of metabolites derived from microorganisms from cultured cells. That is, the culture juice is separated by conventional filtration to obtain filtrate and cells. The filtrate is passed through a DIAION HP-20 (registered trademark of Mitsubishi Chemical Imdustries, Japan) column under alkaline conditions to adsorb the target material. After washing with water, the column is eluted with a straight slope from water to 80% hydrous methanol. The eluted active fractions are concentrated and methanol is distilled off. The resulting concentrate is extracted with n-butanol under acidic conditions of hydrochloric acid. The n-butanol phase is concentrated under reduced pressure, and the concentrate is then subjected to Sephadex LH-20 (registered trademark of Pharmacia Biotech) column chromatography. The collected active fractions are concentrated and dissolved in a mixed solution of ethyl acetate-water (1: 1). This solution is subjected to centrifugal liquid-liquid distribution chromatography (CPC-LLB-M manufactured by Sanki Engineering Co., Ltd.) using the lower layer of the above-mentioned mixture of ethyl acetate-water as a stationary phase. After washing with the upper layer of this mixed solution, the active fraction is eluted reversibly as the lower layer. Further, NA32176A is obtained by Sephadex LH-20 column chromatography treatment. The physicochemical properties of the bioactive substance NA32176A thus obtained are shown below. 1) Appearance: white powder 2) Molecular Weight: 418 3) Molecular formula: C 18 H 30 N 2 O 7 S (measured by high resolution mass spectrum) 4) Solubility: Soluble in lower alcohol, water or dimethyl sulfoxide. 5) Rf value by ODS thin layer chromatography: 0.7 when n-butanol: acetic acid: water (4: 1: 2) is the developing solvent 6) UV Absorption Spectrum: shows terminal absorption in water. 7) IR absorption spectrum: Spectra measured with potassium tablets are shown in FIG. 1. 8) Hydrogen Nuclear Magnetic Resonance Spectrum: Spectra measured in heavy water are shown in FIG. 2. 9) Carbon Nuclear Magnetic Resonance Spectrum: The spectrum measured in heavy water is shown in FIG. 3. The chemical shift data is as follows. 10) color reaction Positive in phosphorus molybdate and palladium chloride The physiologically active substance NA32176A represented by general formula [1E] can also be manufactured by the method similar to the manufacturing method of the compound of general formula [1B] mentioned above. More specifically, the bioactive substance NA32176A is prepared under the conditions similar to those used for the compounds (a) to (f) by using the compound of the formula [3B] with panthethene (the product of combining cysteamine and pantothenic acid with each other). It can be manufactured easily by condensation. Panthene Helv. Chim. It is a compound known by Acta, 35, 1903 (1952), and can be easily prepared by hydrolyzing panthetaine S-benzoyl under alkaline conditions in a conventional manner. [F] `Method for preparing compound of general formula [1F] The compound of general formula [1F] is a compound of the following general formula [2F] (In the above formula, A ' F , B' F and Z ' F have the same meaning as defined in A F , B F and Z F , but if this group contains a functional group, it may be appropriately protected.) Compound of the following general formula [3F] And X ' F and Y' F in the above general formula have the same meaning as defined for X F and Y F , but if this group contains a functional group, this functional group may be appropriately protected), and if necessary, a protecting group It can manufacture by removing. Most of the compounds of the general formula [3F] are commercially available. Specific examples of the compound of the general formula [3F] include piperidine, pyrrolidine, morpholine, N-methylpiperazine, N-phenylpiperazine, diethylamine, di-n-propylamine, diisopropylamine, and the like. to be. In order to perform the said reaction, as long as a compound can condense with the compound of General formula [3F], any condensation method can be used. This reaction is generally carried out in organic solvents, water or mixtures thereof. Organic solvents include aromatic hydrocarbons (e.g. benzene, toluene, etc.), alcohols (e.g. methanol, ethanol, etc.), ethers (e.g. tetrahydrofuran, diethyl ether, etc.), halogenated hydrocarbons (e.g. methylene chloride, chloroform, etc.), Ketones (eg acetone, methyl ethyl ketone, etc.), aprotic polar solvents (eg dimethyl sulfoxide, dimethylformamide, etc.) may be used. Examples of preferred solvents for use include ethers (e.g. tetrahydrofuran, diethyl ether), halogenated hydrocarbons (e.g. methylene chloride, chloroform), ketones (e.g. acetone, methyl ethyl ketone, etc.), aprotic polar solvents (e.g. : Dimethyl sulfoxide, dimethylformamide, etc.), alcohol (for example, methanol, ethanol, etc.), or a mixture of this solvent and water. The reaction generally proceeds in the absence of a catalyst or in the presence of an acid or a base. The reactants used to maintain basic conditions are inorganic bases such as potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate and sodium hydride, or triethylamine, 1,8-diazabicyclo [5.4.0] -undeca- Organic bases, such as 7-yen. The use amount of these reactants is about 0.1 to 20 times mole, preferably about 0.5 to 5 times mole. Since the reaction temperature is not particularly limited, the reaction may be performed under cooling, or may be performed at room temperature or under heating. Preferably the reaction is carried out at a temperature between -50 ° C and 150 ° C. The compound of the formula [2F] is reacted with the compound of the formula [3F] in equimolar amounts. In practice, the compound of the general formula [3F] is used in an amount of excess, such as 1 to 2 moles. The reaction is carried out for 0.1 to 240 hours, preferably 0.1 to 96 hours. The compound of general formula [1F] is a compound of the following general formula [4F] (In the above formula, A ' F , B' F and Z ' F have the same meaning as defined in A F , B F and Z F , but if this group contains a functional group, it may be appropriately protected.) Compound of the following general formula [3F] (X ' F and Y' F in the above general formula has the same meaning as defined for X F and Y F , but if the group contains a functional group, it may be appropriately protected.) And formaldehyde or its equivalent It can be prepared by reacting in the presence and removing the protecting group if necessary. For the details of the compound of the general formula [3F], the foregoing description applies here. The method of condensation of a compound of the general formula [3F] with a compound of the general formula [4F] in the presence of formaldehyde or an equivalent thereof is called a Mannich reaction, and various studies have been carried out (for example, Tetrahedron, 46, 1791 (1990), Synthesis, 1973, 703). This reaction is generally carried out in organic solvents, water or mixtures thereof. Organic solvents include aromatic hydrocarbons (e.g. benzene, toluene, etc.), alcohols (e.g. methanol, ethanol, etc.), ethers (e.g. tetrahydrofuran, diethyl ether, etc.), halogenated hydrocarbons (e.g. methylene chloride, chloroform, etc.), Ketones (eg acetone, methyl ethyl ketone, etc.), aprotic polar solvents (eg dimethyl sulfoxide, dimethylformamide, etc.) may be used. Examples of preferred solvents for use include ethers (e.g. tetrahydrofuran, diethyl ether), halogenated hydrocarbons (e.g. methylene chloride, chloroform), ketones (e.g. acetone, methyl ethyl ketone, etc.), aprotic polar solvents (e.g. : Dimethyl sulfoxide, dimethylformamide, etc.), alcohol (for example, methanol, ethanol, etc.), or a mixture of this solvent and water. The reaction is generally carried out in the presence of a catalyst. If necessary, an acid may be used as a catalyst. Examples of formaldehyde equivalents are 1,3,5-trioxane and bis (dimethylamino) methane. The use amount of formaldehyde and its equivalent is about 0.9 to 100 times mole, preferably about 1 to 20 times mole. Since the reaction temperature is not particularly limited, the reaction may be performed under cooling, or may be performed at room temperature or under heating. Preferably the reaction is carried out at a temperature between 0 ° C and 200 ° C. The compound of formula [4F] is reacted with the compound of formula [3F] in equimolar amounts. In practice, the compound of the general formula [3F] is used in an amount of excess, such as 1 to 2 moles. The reaction is carried out for 0.1 to 360 hours, preferably 0.1 to 120 hours. The compound of general formula [1F] is a compound of the following general formula [5F] (In the above formula, A ' F , B' F and Z ' F have the same meaning as defined in A F , B F and Z F , but when this group contains a functional group, it may be appropriately protected. Leaving group and protecting the carbonyl group at 1 position as appropriate) Compound of the following general formula [3F] And X ' F and Y' F in the above general formula have the same meaning as defined for X F and Y F , but if this group contains a functional group, this functional group may be appropriately protected), and if necessary, a protecting group It can be manufactured easily by removing. The compound of the general formula [3F] has been described above. The conditions used for this reaction are similar to those of the reaction of compounds of the general formulas [2F] and [3F]. Preferred examples of leaving groups are chlorine, bromine, iodine, methanesulfonyloxy, chloromethanesulfonyloxy, trifluoromethanesulfonyloxy, chloromethanesulfonyloxy and (2,3-O-isopropylidene) propylsul Ponyyl. Specific examples of the compound of the general formula [5F] are as follows. (a) 2-[(2,3-O-isopropylidene) propylsulfonyl] methyl-3-oxo-1-cyclopentanecarboxylic acid (b) 2-[(2,3-O-isopropylidene) propylsulfonyl] methyl-3-methoxycarbonylcyclopentanone Representative methods for the preparation of the compounds of the general formula [2F] are shown below. That is, the compounds of the general formula [2F] are formulated with the compounds of the general formula [4F] in the presence of secondary amine If necessary, it can manufacture easily by making it react, heating. (In the above formula, A ' F , B' F and Z ' F have the same meaning as defined in A F , B F and Z F , but if this group contains a functional group, it may be appropriately protected.) The reaction conditions are similar to those used to react the compound of the general formula [3F] with the compound of the general formula [4F]. When it is necessary to further heat, it is preferable to heat at 30 to 200 degreeC. In addition, the compound of the general formula [2F] is prepared by preparing a compound of the general formula [1F] through a Mannich reaction, converting nitrogen of the compound [1F] with an oxidizing agent or alkylating with an alkylating agent to a quaternary salt, It can manufacture easily by heating according to this. Suitable oxidizing agents for use in the oxidation reaction include organic peracids such as m-chloroperbenzoic acid, hydrogen peroxide, organic peroxides and the like. Alkylating agents are methyl iodide, dimethyl sulfate, ethyl iodide and the like. Heating conditions optionally carried out after oxidation or after alkylation are similar to those described above. A 'is F, for example if there is a problem sometimes occur due to the position selectivity in the Mannich reaction in the compounds of the aliphatic group formula [4F], the problem in this case can be avoided as follows. For example, known 3-acetyl-butyrolactone [Bull. Chem. Soc. Jpn., 32, 1282 (1959)] are maintained under acidic or basic conditions to yield 3-methylidene-4-oxo-1-n-pentanoic acid. The reactants used in this reaction are inorganic bases such as sodium hydroxide, organic bases such as triethylamine, 1,8-diazabicyclo [5.4.0] -undeca-7-ene, inorganic acids such as hydrochloric acid, sulfuric acid, and p. Although it is organic acid, such as toluenesulfonic acid, organic bases, such as triethylamine and 1,8- diazabicyclo [5.4.0] -undeca-7-ene, and inorganic acids, such as a sulfuric acid, are preferable. Other methods for solving the location selectivity problem, such as J. Chem. Soc. Chem. Commun., 1974, 253, using a highly regioselective reactant for the Mannich reaction, or site specificity of ketones with enolates as disclosed in Tetrahedron, 46, 987 (1990). After conversion, a method of introducing an aminomethylene unit into the enolate unit may be used. Some of the compounds of the formula [4F] are commercially available as reagents, ie they are, for example, 4-phenyl-4-oxobutanoic acid, 4- (4-methylphenyl) -4-oxobutanoic acid, 4- (4-meth). Methoxyphenyl) -4-oxobutanoic acid, 2-methyl-4-oxo-4-phenylbutyric acid, 4-benzoylbutyric acid and the like. A compound of the general formula [4F], wherein A F is a benzene ring substituted with a benzene ring or an electron donor, is a Friedel-Crafts acylation reaction with maleic anhydride in the presence of Lewis acid such as aluminum chloride. acylation). Synthesis, Coll. III, 109 (1955). Compounds of the general formula [4F] or a reduced product thereof (alcohol product) in which A F is a group other than the above-mentioned groups react the corresponding aldehyde or acid halide of A F with ethyl γ-iodopropionate in the presence of zinc. Modified Reformatsky Reaction [J. Am. Chem. Soc., 109, 8056 (1987). The reaction product is oxidized in a conventional manner to give the corresponding ketone to obtain a compound of the general formula [4F]. In addition, the compounds of the general formula [4F] are prepared by the presence of the corresponding aldehyde and acrylic acid derivatives of A F in the presence of sodium cyanide or 3-benzyl-5- (2-hydroxyethyl) -4-methylthiazolium chloride. It can be prepared by reacting under [Chem. Ber., 109, Section 289, 541 (1976). Furthermore, the compound of the general formula [4F] is dehydrated under reduced pressure while heating the methyl ketone of the corresponding A F with glyoxylic acid and an aldol condensation reaction, and the obtained carbon-carbon double bond is conventionally used, for example, zinc powder. -Reduction using acetic acid [J. Med. Chem., 15, 918 (1972)]. The compound of general formula [5F] can be manufactured, for example, by the following method. In the above formula, A ' F , B' F and Z ' F have the same meaning as defined in A F , B F and Z F , but when the group contains a functional group, the functional group may be appropriately protected and U is released It is group, and you may suitably protect the carbonyl group in 1 position. The compound of the formula [5F-a] reacts the silyl-enol derivative of the compound of the formula [4F] with formaldehyde under acidic conditions or reacts the compound of the formula [4F] with formaldehyde under basic conditions. It can be manufactured from a compound of the general formula [4F] by a modification of a known method for producing β-hydroxyketone. The compound of the general formula [5F] reacts the compound of the general formula [5F-a] thus obtained with a sulfonyl chloride such as p-toluenesulfonyl chloride in the presence of a base if necessary, or in a conventional manner. It can be manufactured easily by reacting with a halogenating agent of a hydroxy group such as thionyl chloride, triphenylphosphine-halogenating agent, triphenylphosphine-diethyl azodicarboxylate-halogenating agent and the like. The compound of the general formula [5F] thus produced may be used in the subsequent reaction without separating. The compounds (a) and (b) described above are the same as the compounds (c) and (d) in the preparation of the compound of the general formula [1B] and can be produced by the methods described for these compounds. Hereinafter, the medicinal properties of the present invention will be described in more detail. It has been found that the compounds of the present invention and pharmacologically acceptable salts thereof exhibit potent cell differentiation promoting action. Therefore, the composition containing the compound of the present invention and a pharmacologically acceptable salt thereof as an active ingredient can be used as a medicament for treating disorders of the central and peripheral nerves because it is effective in promoting neuronal differentiation. In the case of using the compound of the present invention and a pharmacologically acceptable salt thereof as a promoter for neuronal differentiation, the composition is used as an injection, drop, granule, tablet, granule, particulate, powder, capsule, liquid, inhalant, suppository, Various formulations, such as eye drops, plasters, ointments, and sprays, can be used alone or in combination with various pharmaceutically acceptable additives such as carriers, excipients, diluents, and dissolution aids. The route of administration is selected from oral and parenteral administration (systemic and topical administration). The compounds of the present invention and pharmacologically acceptable salts thereof contained in the pharmaceutical composition vary depending on the dosage form, but preferably in the range of an amount of 0.1 to 100 wt.%. Dosage is determined according to the age, sex, weight, health condition and therapeutic purpose of the patient, and generally ranges from about 0.001 to 5000 mg / kg / day. The present inventors have conducted intensive studies on cystacycline derivatives, and as a result, novel compounds and pharmacologically acceptable compounds represented by general formulas [1A], [1B], [1C], [1D], [1E] and [1F] The present invention has been completed by finding salts thereof. The present invention relates to the following compounds and compositions containing them. 1) Cyclopentanone derivative represented by the general formula [1A] or a pharmacologically acceptable salt thereof: In the above formula, X A is O, S, SO, SO 2 or NH; Y A is a substituted or unsubstituted linear or branched aliphatic hydrocarbon group having 1 to 20 carbon atoms or a substituted or unsubstituted monocyclic aromatic heterocyclic or aromatic hydrocarbon group having 3 to 6 carbon atoms; Z1 A , Z2 A and Z3 A may be the same or different, and each independently represent a carboxyl group or a group derived therefrom, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, a hydroxy group or a group derived therefrom, an amino group Or a group derived therefrom, a sulfonate group or a group derived therefrom, a phosphate group or a group derived therefrom, a monocyclic heteroaryl group, halogen or hydrogen, or Z 2 A and Z 3 A are bonded together to be substituted or unsubstituted To form an aromatic hydrocarbon or aromatic heterocycle of the ring; And Z1 A is a carboxyl group or group derived therefrom, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, a hydroxy group or a group derived therefrom, an amino group or a group derived therefrom, halogen or hydrogen, provided that Z2 A and When Z 3 A is all hydrogen, Z 1 A is a hydroxy group or a group derived therefrom, an amino group or a group derived therefrom, a sulfonate group or a monocyclic aromatic heterocyclic ring, halogen or hydrogen, and Y A is substituted with 1 to 6 carbon atoms. Or an unsubstituted linear or branched aliphatic hydrocarbon group; Except for the following cases (1) to (7): (1) when Z1 A and Z2 A are hydrogen, X A is S, Y A is a methyl group or benzyl group, Z3 A is a methoxycarbonyl group, (2) when Z1 A and Z2 A are hydrogen, X A is O or N, Y A is a benzyl group, Z3 A is a carboxy group, methoxycarbonyl group or ethoxycarbonyl group, (3) X A is N or O, Z 1 A and Z 3 A are hydrogen, Z 2 A is a carboxy group, methoxycarbonyl group, (4) X A is O, Z 1 A is a hydroxyl group or a group derived therefrom, Z 2 A is a hydrogen, Z 3 A is an amino group or a group derived therefrom, (5) X A is S, Y1 A is a phenyl group, Z1 A is a dimethoxymethyl group, Z2 A and Z3 A are hydrogen, (6) X A is O, Y 1 A is a methyl group, Z 1 A is a 1-methoxy-1-phenylthiomethyl group, Z 2 A and Z 3 A are hydrogen, (7) Z 1 A is S, SO or SO 2 , Z 2 A is a hydroxy group or a group derived therefrom, Z 3 A is hydrogen. 2,3-di-substituted cyclopentanone derivatives of the general formula [1B] or pharmacologically acceptable salts thereof: In the above formula, X B is O, S, SO, SO 2 or NH; Y B is Unsubstituted or substituted straight-chain or branched aliphatic hydrocarbon group having 7 to 20 carbon atoms, Linear or branched aliphatic hydrocarbon groups having 1 to 6 carbon atoms, Wherein at least one hydrogen may be substituted with COW1 (wherein W1 is an unsubstituted or substituted aromatic heterocycle or a saturated heterocycle), at least one hydrogen may be further substituted with a group derived from an amino group, or at least one hydrogen is NHCOV1 (where V1 is an alkyl group having 2 to 5 carbon atoms having 4 to 11 halogen atoms), and at least one hydrogen may be further substituted with a carboxy group or a group derived therefrom, Or at least one hydrogen may be substituted with a substituted or unsubstituted monocyclic aromatic heterocycle, and at least one hydrogen may be further substituted with an amino group or a group derived therefrom; Or a substituted or unsubstituted monocyclic aromatic heterocyclic ring or aromatic heterocyclic ring having 3 to 6 carbon atoms; Z B is a carboxyl group or a group derived therefrom, a sulfonate group or a group derived therefrom, a phosphate group or a group derived therefrom, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, a hydroxy group, OR1 (where R1 is Unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, unsubstituted or substituted acyl group having 1 to 5 carbon atoms, NHCOR2 (where R2 is unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), NHSO 2 R2 '(where R2' is an unsubstituted or substituted alkyl or phenyl group having 1 to 4 carbon atoms), a monocyclic aromatic heterocyclic ring, halogen or hydrogen. Cyclopentenone derivatives of the general formula [1C] or pharmacologically acceptable salts thereof: In the above formula, Ring A has one double bond conjugated with oxo; X C is O, S, SO, SO 2 or NH; Y C is a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 6 carbon atoms, or a substituted or unsubstituted monocyclic aromatic heterocyclic or aromatic hydrocarbon group having 3 to 6 carbon atoms; Z 1 C , Z 2 C and Z 3 C may be the same or different, and each independently represent a carboxy group or a group derived therefrom, a hydroxy group or a group derived therefrom, an amino group or a group derived therefrom, or a substitution of 1 to 4 carbon atoms. Or an unsubstituted alkyl or alkenyl group, a monocyclic aromatic heterocyclic ring, a halogen atom or hydrogen; Provided that when X C is O or NH, Z 1 C and Z 3 C are not hydrogen, and Z 2 C is not hydrogen or a hydroxy group or a group derived therefrom. Ketone derivatives of the general formula [1D] or pharmacologically acceptable salts thereof: In the above formula, A D is an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 4 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon, a heterocyclic ring or a saturated heterocyclic ring; B D is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 4 carbon atoms; or A D and B D are bonded together to form an unsubstituted or substituted cycloalkane-1-one ring having 3 to 7 carbon atoms (excluding 5 carbon atoms); X D is O, S, SO, SO 2 or NH; Y D is a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 6 carbon atoms or a substituted or unsubstituted monocyclic aromatic heterocyclic or aromatic hydrocarbon group having 3 to 6 carbon atoms; Z D is a carboxyl group or group derived therefrom, an unsubstituted or substituted alkyl group or alkenyl group, hydroxy group or group derived therefrom, an amino group or a group derived therefrom, a sulfonate group or derived therefrom Group, phosphate group or group derived therefrom, monocyclic aromatic heterocycle, halogen or hydrogen; However, when A D and B D are bonded together to form a cyclobutane ring, the following (1) to (4) are excluded: (1) X D is O, Y D is a methyl group, n-octyl group or n-hexadecyl group, and Z D is a methoxycarbonyl group; (2) X D is O, Y D is a benzyl group, and Z D is a benzyloxymethyl group; (3) X D is O, Y D is p-methoxybenzyl group, and Z D is p-methoxybenzyloxymethyl group; (4) When X D is O, Y D is trityl group, Z D is trityloxymethyl group, or A D is an unsubstituted benzene ring and B D is hydrogen, X D is S, Y D is methyl, ethyl Or isopropyl group and Z D is a carboxy group. Compound of formula [1E] or a pharmacologically acceptable salt thereof: Β-di-substituted aminoketone derivatives of the general formula [1F] or pharmacologically acceptable salts thereof: In the above formula, A F is an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 4 carbon atoms, or an unsubstituted or substituted aromatic hydrocarbon ring, an aromatic heterocycle, or a saturated heterocycle; B F is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 4 carbon atoms; A F and B F are bonded together to form an unsubstituted or substituted cycloalkane-1-one ring having 3 to 7 carbon atoms or fused with an aromatic hydrocarbon or aromatic heterocycle, or cycloalkane-1 having 3 to 7 carbon atoms. -Form a warm ring; X F and Y F are each an unsubstituted or substituted linear or branched aliphatic hydrocarbon group having 1 to 10 carbon atoms, or X F and Y F are bonded directly to each other or through a hetero atom to form an unsubstituted or substituted group. To form a heterocycle; Z F is a carboxyl group or group derived therefrom, an unsubstituted or substituted alkyl group or alkenyl group, hydroxy group or group derived therefrom, an amino group or group derived therefrom, a sulfonate group or derived therefrom Group, phosphate group or group derived therefrom, monocyclic aromatic heterocycle or halogen; However, when A F is an unsubstituted benzene ring, except that B F is hydrogen, X F and Y F are directly bonded to each other to form a piperidine ring, and Z F is a carboxy group. 2) The cyclopentanone derivative or pharmacologically acceptable salt thereof according to 1), wherein the general formula [1A] is defined as follows: In the above formula [1A], X A is S, O, SO or SO; Y A is a straight or branched aliphatic hydrocarbon group having 1 to 20 carbon atoms, wherein at least one hydrogen atom is substituted with a carboxyl group or a group derived therefrom or an amino group or a group derived therefrom; Z1 A , Z2 A and Z3 A may be the same or different, and each independently represent a carboxyl group or a group derived therefrom, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, a hydroxy group or a group derived therefrom, an amino group Or a group derived therefrom, a monocyclic aromatic heterocycle, halogen or hydrogen, or Z2 A and Z3 A combine together to form a substituted or unsubstituted aromatic hydrocarbon or aromatic heterocycle; And Z 1 A is a carboxyl group or group derived therefrom, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, a hydroxyl group or a group derived therefrom, an amino group or a group derived therefrom, halogen or hydrogen. 3) The cyclopentanone derivative according to 2), or a pharmacologically acceptable salt thereof, wherein the general formula [1A] is defined as follows: In the above formula [1A], X A is S; Y A is a linear or branched aliphatic hydrocarbon group having 1 to 6 carbon atoms, Wherein at least one hydrogen is a carboxyl group, COOR1 (wherein R1 is a substituted or unsubstituted alkyl, alkenyl or alkynyl group having 1 to 4 carbon atoms), COW1 (where W1 is an unsubstituted or substituted by a carboxyl group or a group derived therefrom) Ring) or NR2R3 (wherein R2 and R3 may be the same or different, and each independently represent hydrogen, unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or unsubstituted or substituted acyl group having 1 to 5 carbon atoms) Substituted with; Z1 A , Z2 A and Z3 A may each be the same or different, each independently represent a carboxy group, COOR4 (where R4 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), CONR5R6 (where R5 and R6 are each the same) Or may be different from each other independently hydrogen or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, a cyano group, a hydroxy group, OR7 (where R7 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or carbon atoms) NR8R9 (where R8 and R9 may each be the same or different), and each independently hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or a carbon atom having 1 to 5 carbon atoms; 5 unsubstituted or substituted acyl group, CH 2 OR10 (where R10 is hydrogen, unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or unsubstituted or substituted acyl group having 1 to 5 carbon atoms), Chlorine, Fluorine Represents hydrogen; Z2 A and Z3 A combine together to form a substituted or unsubstituted aromatic hydrocarbon; Z1 A is a carboxy group, COOR4 (where R4 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), CONR5R6 (where R5 and R6 may each be the same or different, and are each independently hydrogen or carbon atoms having 1 to 4 carbon atoms) Substituted or unsubstituted alkyl group), cyano group, hydroxy group, OR7 (where R7 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms), NR8R9 (Wherein R8 and R9 may each be the same or different, and each independently represent hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms), CH 2 OR10 R10 is hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms, and chlorine, fluorine or hydrogen. 4) The cyclopentanone derivative of the general formula [1A] or a pharmacologically acceptable salt thereof according to 3) above: In the general formula [1A] above, X A is S; Y A is a linear aliphatic hydrocarbon group having 1 to 6 carbon atoms, Wherein at least two hydrogens are substituted with a carboxy group, COOR1 '(where R1' is an alkyl group, alkenyl group or alkynyl group having 1 to 4 carbon atoms), COW2 (where W2 is COOR11 (R11 is an alkyl group having 1 to 4 carbon atoms) or Unsubstituted saturated heterocyclic ring) or NHCOR12 wherein R12 is an alkyl group having 1 to 4 carbon atoms; Z1 A , Z2 A and Z3 A may each be the same or different and each independently represent a carboxy group, COOR4 '(where R4' is an alkyl group having 1 to 4 carbon atoms), a hydroxy group, OCOR13 (where R13 is 1 to 4 carbon atoms) Alkyl group), CH 2 0R 10 ′ where R 10 ′ is hydrogen, an alkyl group having 1 to 4 carbon atoms, or an acyl group having 1 to 5 carbon atoms; Z 2 A and Z 3 A are bonded together to form a benzene ring unsubstituted or substituted with an alkyl group having 1 to 4 carbon atoms, an alkyloxy group having 1 to 4 carbon atoms, a nitro group, a trifluoromethyl group or a halogen; Z1 A is a carboxy group, COOR4 '(where R4' is an alkyl group having 1 to 4 carbon atoms), a hydroxy group, OCOR13 (where R13 is an alkyl group having 1 to 4 carbon atoms), CH 2 0R10 '(where R10' is hydrogen, An alkyl group having 1 to 4 carbon atoms or an acyl group having 1 to 5 carbon atoms) or hydrogen. 5) The cyclopentanone derivative of the general formula [1A] or a pharmacologically acceptable salt thereof according to 4) above: In the general formula [1A] above, X A is S; Y A is a linear aliphatic hydrocarbon group having 1 to 6 carbon atoms, Wherein one hydrogen is substituted with a carboxy group, methoxycarbonyl group, COW3, where W3 may be substituted or unsubstituted with a methoxycarbonyl group as a pyrrolidine, piperidine, azetidine, morpholine or piperazine ring, and another One hydrogen is substituted with an acetylamino group; Z1 A , Z2 A and Z3 A may each be the same or different and each independently represent a carboxy group, methoxycarbonyl group, hydroxy group, acetyloxymethyl group, hydroxymethyl group or hydrogen; or Z2 A and Z3 A combine together to form an unsubstituted benzene ring; Z1 A is a carboxy group, methoxycarbonyl group, hydroxy group, acetyloxymethyl group, hydroxymethyl group or hydrogen. 6) The cyclopentanone derivative of the general formula [1A] or a pharmacologically acceptable salt thereof according to item 5), selected from the group consisting of substituents defined as follows: In the general formula [1A] above, (I) X A is S, Y A is 2-acetylamino-2-carboxyethyl, Z1 A and Z3 A are hydrogen, and Z2 A is a carboxy group; (II) X A is S, Y A is 2-acetylamino-2-methoxycarbonylethyl, Z1 A and Z3 A are hydrogen, and Z2 A is a carboxy group; (III) X A is S, Y A is 2-acetylamino-2-carboxyethyl, Z1 A and Z3 A are hydrogen, and a Z2 A hydroxy group; (IV) X A is S, Y A is 2-acetylamino-3-oxo-3- {1- (2-methoxycarbonyl) pyrrolidinyl} propyl, Z1 A and Z3 A are hydrogen, and Z2 A A hydroxy group; (V) X A is S, Y A is 2-acetylamino-2-methoxycarbonylethyl, Z 2 A and Z 3 A are bonded together to form an unsubstituted benzene ring, and Z 1 A is a carboxy group; And (VI) X A is S, Y A is 2-acetylamino-2-carboxyethyl, Z2 A and Z3 A are bonded together to form an unsubstituted benzene ring, and Z1 A is a carboxy group. 7) The 2,3-di-substituted cyclopentanone derivative of the general formula [1B] according to 1) above or a pharmacologically acceptable salt thereof: In the above general formula [1B], X B is S, O or SO; Y B is a straight or branched aliphatic hydrocarbon group having 7 to 20 carbon atoms, wherein at least one hydrogen may be optionally substituted with a carboxyl group or a group derived therefrom or an amino group or a group derived therefrom; Z B is a carboxy group, COOR3 (where R3 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), CH 2 OR4 (where R4 is hydrogen or an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), or CH 2 OCOR5 (where R5 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms). 8) The 2,3-di-substituted cyclopentanone derivative of the general formula [1B] according to the above 7) or a pharmacologically acceptable salt thereof: In the above general formula [1B], X B is S; Y B is a linear aliphatic hydrocarbon group having 7 to 20 carbon atoms (where at least two hydrogens are a carboxy group, COOR6 (where R6 is an alkyl group having 1 to 4 carbon atoms, an alkenyl group or an alkynyl group) or NR7R8 (where R7 and R8 are the same) May be different from each other, and are each independently substituted with hydrogen, an alkyl group having 1 to 4 carbon atoms or an acyl group having 1 to 5 carbon atoms), Z B is a carboxy group, methoxycarbonyl group, hydroxymethyl group or acetyloxymethyl group. 9) The 2,3-di-substituted cyclopentanone derivative of the general formula [1B] as defined in the above 8) or a pharmacologically acceptable salt thereof: In the above general formula [1B], X B is S; Y B is 11-acetylamino-11-carboxy-n-undecyl, Z B is a carboxy group. 10) The 2,3-di-substituted cyclopentanone derivative of the general formula [1B] as defined in the above 1) or a pharmacologically acceptable salt thereof: In the above general formula [1B], X B is S, O or SO; Y B is a linear or branched aliphatic hydrocarbon group having 1 to 6 carbon atoms, and at least one hydrogen is COW2 {where W2 is a saturated or unsubstituted or substituted with a hydroxyalkyl group, phenyl group or carboxy group having 1 to 4 carbon atoms Heterocyclic ring, COOR9 (wherein R9 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), and at least another hydrogen is NR10R11, where R10 and R11 may be the same or different, and each independently Hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms; Z B is a carboxy group, COOR3 (where R3 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), CH 2 0R4 (where R4 is hydrogen or an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), or CH 2 0COR 5, wherein R 5 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms. 11) The 2,3-di-substituted cyclopentanone derivative of the general formula [1B] according to the above 10) or a pharmacologically acceptable salt thereof: In the above general formula [1B], X B is S; Y B is a linear or branched aliphatic hydrocarbon group having 1 to 6 carbon atoms (wherein one hydrogen is COW3 (wherein W3 is substituted with a carboxyl group, methoxycarbonyl group, 2-hydroxyethyl group, phenyl group or tert-butoxycarbonyl group or May be unsubstituted, substituted with 1-azetidinyl, 1-piperidyl, 1-pyrrolidinyl, 1-piperazinyl or 4-morpholinyl group, and the other hydrogen is NHCOR12, where R12 is Substituted with an alkyl group of 1 to 4 carbon atoms; Z B is a carboxy group, methoxycarbonyl group, hydroxymethyl group or acetyloxy group. 12) The 2,3-di-substituted cyclopentanone derivative of the general formula [1B] according to 1) above, or a pharmacologically acceptable salt thereof, according to 11) above: In the above general formula [1B], X B is S; Y B is 2-acetylamino-3-oxo-3- (1-pyrrolidinyl) propyl, 2-acetylamino-3- {1- (2-methoxycarbonyl) pyrrolidinyl} -3-oxopropyl , 2-acetylamino-3-oxo-3- (1-piperidyl) propyl, 2-acetylamino-3- (4-morpholinyl) -3-oxopropyl, 2-acetylamino-3- {1 -(2-methoxycarbonyl) azetidinyl} -3-oxopropyl, 2-acetylamino-3-oxo-3- (1-piperazinyl) propyl, 2-acetylamino-3- [1- { 4- (2-hydroxyethyl) piperazinyl}]-3-oxopropyl, 2-acetylamino-3- {1- (4-phenylpiperazinyl)}-3-oxopropyl or 2-acetylamino- 3- {1- (4-tert-butoxycarbonylpiperazinyl)}-3-oxopropyl; Z B is a carboxyl group or a methoxycarbonyl group. 13) The 2,3-di-substituted cyclopentanone derivative of the general formula [1B] according to 1) above, or a pharmacologically acceptable salt thereof according to 1) above, which is defined as follows: In the above general formula [1B], X B is S, O or SO; Y B is a linear or branched aliphatic hydrocarbon group having 1 to 6 carbon atoms, wherein at least one hydrogen is substituted with NHCOV1 (where V1 is an alkyl group having 2 to 5 carbon atoms and 4 to 11 halogen atoms), and at least The other hydrogen may be further substituted with a carboxy group or COOR 13, wherein R 13 is an unsubstituted or substituted alkyl, alkenyl or alkynyl group having 1 to 4 carbon atoms. Z B is a carboxy group, COOR3 (where R3 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), CH 2 0R4 (where R4 is hydrogen or an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), or CH 2 0COR 5, wherein R 5 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms. 14) The 2,3-di-substituted cyclopentanone derivative of the general formula [1B] as described in the above 1), or a pharmacologically acceptable salt thereof, as defined in the above 13), wherein: In the above general formula [1B], X B is S; Y B is a linear aliphatic hydrocarbon group having 1 to 6 carbon atoms, where one hydrogen is substituted with NHCOV2 (where V2 is an alkyl group having 2 to 5 carbon atoms and 4 to 11 halogen atoms), and the other hydrogen is Is further substituted with a carboxy group or COOR13 'wherein R13' is an alkyl, alkenyl or alkynyl group having 1 to 4 carbon atoms. Z B is a carboxy group, methoxycarbonyl group, hydroxymethyl group or acetyloxymethyl group. 15) The 2,3-di-substituted cyclopentanone derivative of the general formula [1B] as described in the above 1), or a pharmacologically acceptable salt thereof, according to the above 14), which is defined as follows: In the above general formula [1B], X B is S; Y B is 2-carboxy-2- (pentafluoropropionyl) aminoethyl; Z B is a carboxy group or a hydroxymethyl group. 16) The 2,3-di-substituted cyclopentanone derivative of the general formula [1B] according to 1) above, or a pharmacologically acceptable salt thereof, as defined in 1) above: In the above general formula [1B], X B is S, O or SO; Y B is a linear or branched aliphatic hydrocarbon group having 1 to 6 carbon atoms (where at least one hydrogen is substituted with a substituted or unsubstituted monocyclic heterocycle, and at least another hydrogen is NR15R16 (where R15 and R16 are each May be the same as or different from each other, and are each independently substituted with hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or an acyl group having 1 to 5 carbon atoms). Z B is a carboxy group, COOR3 (where R3 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), CH 2 0R4 (where R4 is hydrogen or an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), or CH 2 0COR 5, wherein R 5 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms. 17) The 2,3-di-substituted cyclopentanone derivative of the general formula [1B] according to the above 1), or a pharmacologically acceptable salt thereof according to the above 16), which is defined as follows: In the above general formula [1B], X B is S; Y B is a linear aliphatic hydrocarbon group having 1 to 4 carbon atoms (where one hydrogen is substituted with a pyridine ring or 5-tetrazolyl unsubstituted or substituted with an alkyl group having 1 to 4 carbon atoms, and the other hydrogen is May be further substituted with NHCOR 17, wherein R 17 is an alkyl group having 1 to 4 carbon atoms. Z B is a carboxy group, methoxycarbonyl group, hydroxymethyl group or acetyloxymethyl group. 18) The 2,3-di-substituted cyclopentanone derivative of the general formula [1B] according to the above 1), or a pharmacologically acceptable salt thereof, as defined in the above 17) as defined below: In the above general formula [1B], X B is S; Y B is 3- (3-pyridyl) propyl, 3- {3- (1-methylpyridinium iodide)} propyl or 2-acetylamino-2- (5-tetrazolyl) ethyl; Z B is a carboxyl group or a methoxycarbonyl group. 19) The cyclopentenone derivative of the general formula [1C] as described in 1) above, or a pharmacologically acceptable salt thereof, as defined in the above 1). In the above general formula [1C], Ring A forms an oxo conjugated double bond with carbon atoms bonded to CH 2 -X C -Y C ; X C is S, O or SO; Y C is an aliphatic hydrocarbon group having 1 to 6 carbon atoms, wherein at least one hydrogen is substituted with a carboxyl group or a group derived therefrom, an amino group or a group derived therefrom, or a hydroxy group or a group derived therefrom; Z 1 C , Z 2 C and Z 3 C may each be the same or different, and each independently represent a carboxyl group or a group derived therefrom, a hydroxy group or a group derived therefrom or an amino group or a group derived therefrom, or a substitution of 1 to 4 carbon atoms. Or an unsubstituted alkyl or alkenyl group, a monocyclic aromatic heterocycle, halogen or hydrogen. 20) The cyclopentenone derivative of the general formula [1C] according to item 1), or a pharmacologically acceptable salt thereof according to item 19), as defined below: In the above general formula [1C], Ring A forms an oxo conjugated double bond with carbon atoms bonded to CH 2 -X C -Y C ; X C is S, O or SO; Y C is an aliphatic hydrocarbon group having 1 to 6 carbon atoms (where at least one hydrogen is a carboxy group, COOR1 (where R1 is a substituted or unsubstituted alkyl or alkenyl group having 1 to 4 carbon atoms), CONR2R3 (where R2 and R3, respectively) May be the same as or different from each other, and each independently hydrogen or an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, COW (where W is a carboxyl group or a group derived therefrom, or an amino group or a group derived therefrom) Or unsubstituted heterocyclic ring, NR4R5 (wherein R4 and R5 may each be the same or different, and each independently hydrogen, unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or unsubstituted or substituted with 1 to 5 carbon atoms) OR6 (where R6 is hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms) Hwandoem shown below); Z 1 C , Z 2 C and Z 3 C are each independently a carboxyl group, COOR 7 (where R 7 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), CONR 8 R 9 (where R 8 and R 9 may be the same or different, respectively, independently) Hydrogen or a C1-4 unsubstituted or substituted alkyl group), a cyano group, CH 2 OR10 (where R10 is hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or 1 to 5 carbon atoms) Unsubstituted or substituted acyl group, hydroxy group, OCOR11 (where R11 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), NR12R13 (where R12 and R13 may each be the same or different, each independently hydrogen , An unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms), 5-tetrazolyl, chlorine, fluorine or hydrogen. 21) The cyclopentenone derivative of the general formula [1C] as described in 1) above, or a pharmacologically acceptable salt thereof, as defined in the above 20), wherein: In the above general formula [1C], Ring A forms an oxo conjugated double bond with carbon atoms bonded to CH 2 -X C -Y C ; X C is S; Y C is an aliphatic hydrocarbon group of 1 to 6 carbon atoms (where at least two hydrogens are carboxyl groups, COOR1 '(where R1' is an alkyl or alkenyl group of 1 to 4 carbon atoms), NHCOR14 (where R14 is hydrogen fluorine) Optionally substituted with a C1-4 alkyl group), a hydroxy group, or OCOR15, where R15 is a C1-4 alkyl group; Z1 C , Z2 C and Z3 C are each a carboxy group, COOR7 '(where R7' is an alkyl group having 1 to 4 carbon atoms), or CH 2 OR10 '(where R10' is hydrogen or an acyl group having 1 to 5 carbon atoms) Im). 22) The cyclopentenone derivative of the general formula [1C] as described in 1) above, or a pharmacologically acceptable salt thereof, as defined in the above 21) as defined below: In the above general formula [1C], Ring A forms an oxo conjugated double bond with carbon atoms bonded to CH 2 -X C -Y C ; X C is S; Y C is 2-acetylamino-2-carboxyethyl; Z 1 C or Z 2 C is a hydroxyl group, and the rest of Z 1 C , Z 2 C and Z 3 C are all hydrogen. 23) The cyclopentenone derivative of the general formula [1C] as described in 1) above, or a pharmacologically acceptable salt thereof, as defined in the above 1). In the above general formula [1C], Ring A forms an oxo conjugated double bond without containing carbon atoms bonded to CH 2 -X C -Y C ; X C is S, O or SO; Y C is an aliphatic hydrocarbon group having 1 to 6 carbon atoms, wherein at least one hydrogen is substituted with a carboxyl group or a group derived therefrom or an amino group or a group derived from or a hydroxy group or a group derived therefrom, Z 1 A , Z 2 A and Z 3 A are each a carboxyl group or a group derived therefrom, an unsubstituted or substituted alkyl or alkenyl group, a hydroxy group or a group derived therefrom, an amino group or a group derived therefrom, having 1 to 4 carbon atoms, Monocyclic aromatic heterocycle, halogen or hydrogen. 24) The cyclopentenone derivative of the general formula [1C] according to the above 1), or a pharmacologically acceptable salt thereof, as defined in the above 23), as defined below: In the above general formula [1C], Ring A forms an oxo conjugated double bond without containing carbon atoms bonded to CH 2 -X C -Y C ; X C is S, O or SO; Y C is an aliphatic hydrocarbon group having 1 to 6 carbon atoms (where at least one hydrogen is a carboxy group, COOR1 (where R1 is a substituted or unsubstituted alkyl or alkenyl group having 1 to 4 carbon atoms), CONR2R3 (where R2 and R3, respectively) May be the same as or different from each other, and each independently hydrogen or an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, COW (where W is a carboxyl group or a group derived therefrom, or an amino group or a group derived therefrom) Or unsubstituted heterocyclic ring, NR4R5 (wherein R4 and R5 may each be the same or different, and each independently hydrogen, unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or unsubstituted or substituted with 1 to 5 carbon atoms) OR6 (where R6 is hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms) Hwandoem shown below); Z 1 C , Z 2 C and Z 3 C are each independently a carboxyl group, COOR 7 (where R 7 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), CONR 8 R 9 (where R 8 and R 9 may be the same or different, respectively, independently) Hydrogen or a C1-4 unsubstituted or substituted alkyl group), a cyano group, CH 2 OR10 (where R10 is hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or 1 to 5 carbon atoms) Unsubstituted or substituted acyl group, hydroxy group, OCOR11 (where R11 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), NR12R13 (where R12 and R13 may each be the same or different, each independently hydrogen , An unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms), 5-tetrazolyl, chlorine, fluorine or hydrogen. 25) The cyclopentenone derivative of the general formula [1C] according to the above 1), or a pharmacologically acceptable salt thereof, as defined in the above 24), as defined below: In the above general formula [1C], Ring A forms an oxo conjugated double bond without containing carbon atoms bonded to CH 2 -X C -Y C ; X C is S; Y C is an aliphatic hydrocarbon group of 1 to 6 carbon atoms (where at least two hydrogens are carboxyl groups, COOR1 '(where R1' is an alkyl or alkenyl group of 1 to 4 carbon atoms), NHCOR14 (where R14 is hydrogen fluorine) Optionally substituted with an alkyl group having 1 to 4 carbon atoms), a hydroxy group, or OCOR15, wherein R15 is substituted with an alkyl group having 1 to 4 carbon atoms; Z1 C , Z2 C and Z3 C are each a carboxy group, COOR7 '(where R7' is an alkyl group having 1 to 4 carbon atoms), or CH 2 OR10 '(where R10' is hydrogen or an acyl group having 1 to 5 carbon atoms) Im). 26) The cyclopentenone derivative of the general formula [1C] according to the above 1), or a pharmacologically acceptable salt thereof, as defined in the above 25), as defined below: In the above general formula [1C], Ring A forms an oxo conjugated double bond without containing carbon atoms bonded to CH 2 -X C -Y C ; X C is S; Y C is 2-acetylamino-2-carboxyethyl; Z1 C , Z2 C and Z3 C are all hydrogen. 27) The ketone derivative of the general formula [1D] according to 1) above, or a pharmacologically acceptable salt thereof, as defined in the above 1), wherein: In the general formula [1D] above, A D is an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 4 carbon atoms; B D is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 4 carbon atoms; X D is S, O or SO; Y D is an aliphatic hydrocarbon group having 1 to 6 carbon atoms, wherein at least one hydrogen is substituted with a carboxyl group or a group derived therefrom, an amino group or a group derived therefrom, or a hydroxy group or a group derived therefrom; Z D is a carboxyl group or a group derived therefrom, an unsubstituted or substituted alkyl or alkenyl group, a hydroxy group or a group derived therefrom, an amino group or a group derived therefrom, a monocyclic aromatic heterocycle, a halogen having 1 to 4 carbon atoms Or hydrogen. 28) The ketone derivative of the general formula [1D] according to the above 1) or pharmacologically acceptable salt thereof, as defined in the above 27), as defined below: In the general formula [1D] above, A D is an aliphatic hydrocarbon group having 1 to 4 carbon atoms; B D is hydrogen or an aliphatic hydrocarbon group having 1 to 4 carbon atoms; X D is S, O or SO; Y D is an aliphatic hydrocarbon group having 1 to 6 carbon atoms (where at least one hydrogen is a carboxyl group, COOR1 (where R1 is a substituted or unsubstituted alkyl or alkenyl group having 1 to 4 carbon atoms), CONR2R3 (where R2 and R3, respectively) May be the same as or different from each other, and each independently hydrogen or an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, COW (where W is a carboxyl group or group derived therefrom or an amino group or group derived therefrom) Ring or substituted heterocyclic ring, NR4R5, wherein R4 and R5 may each be the same or different, and each independently hydrogen, unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or unsubstituted or substituted with 1 to 5 carbon atoms OR 6, where R 6 is hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms Hwandoem shown below); Z D is a carboxyl group, COOR7 (where R7 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), CONR8R9 (where R8 and R9 may be the same or different, respectively, and are each independently hydrogen or 1 to 4 carbon atoms) Unsubstituted or substituted alkyl group, cyano group, CH 2 OR10 (where R10 is hydrogen, unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or unsubstituted or substituted acyl group having 1 to 5 carbon atoms) , Hydroxy group, OCOR11 (where R11 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), NR12R13 (where R12 and R13 may each be the same or different, and are each independently hydrogen, unsubstituted 1 to 4 carbon atoms) Or a substituted alkyl group, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms), 5-tetrazolyl, chlorine, fluorine or hydrogen. 29) The ketone derivative of the general formula [1D] according to the above 1) or pharmacologically acceptable salt thereof, as defined in the above 28), as defined below: In the general formula [1D] above, A D is an alkyl group having 1 to 4 carbon atoms; B D is hydrogen or an alkyl group having 1 to 4 carbon atoms; X D is S; Y D is an aliphatic hydrocarbon group of 1 to 6 carbon atoms (where at least two hydrogens are carboxyl groups, COOR1 '(where R1' is an alkyl or alkenyl group of 1 to 4 carbon atoms), NHCOR14 (where R14 is hydrogen fluorine) Optionally substituted with a C1-4 alkyl group), a hydroxy group, or OCOR15, where R15 is a C1-4 alkyl group; Z D is a carboxy group, COOR7 '(where R7' is an alkyl group having 1 to 4 carbon atoms), or CH 2 OR10 '(where R10' is an acyl group having 1 to 5 carbon atoms). 30) The ketone derivative of the general formula [1D] according to the above 1) or pharmacologically acceptable salt thereof, as defined in the above 29), as defined below: In the general formula [1D] above, A D is methyl; B D is hydrogen; X D is S; Y D is 2-acetylamino-2-carboxyethyl or 2-acetylamino-2-methoxycarbonylethyl; Z D is carboxyl group, methoxycarbonyl, acetoxymethyl or hydroxymethyl. 31) The ketone derivative of the general formula [1D] according to 1) above, or a pharmacologically acceptable salt thereof, as defined in 1) above: In the general formula [1D] above, A D is an unsubstituted or substituted aromatic hydrocarbon, aromatic heterocyclic ring or saturated heterocyclic ring; B D is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 4 carbon atoms; X D is S, O or SO; Y D is an aliphatic hydrocarbon group having 1 to 6 carbon atoms, wherein at least one hydrogen is substituted with a carboxyl group or a group derived therefrom, an amino group or a group derived therefrom or a hydroxy group or a group derived therefrom; Z D is a carboxyl group or group derived therefrom, an unsubstituted or substituted alkyl group or alkenyl group, hydroxy group or group derived therefrom, an amino group or a group derived therefrom, a monocyclic aromatic heterocycle, a halogen having 1 to 4 carbon atoms Or hydrogen. 32) The ketone derivative of the general formula [1D] as described in 1) above, or a pharmacologically acceptable salt thereof, as defined in the above 31), wherein: In the general formula [1D] above, A D is an unsubstituted benzene ring, and when substituted, the hydrogen atoms of 1 to 3 are unsubstituted or substituted alkyl groups having 1 to 4 carbon atoms, halogen, hydroxy groups, alkoxy groups having 1 to 4 carbon atoms, amino groups, and carbon atoms 1-4 alkyl- or dialkylamino groups, thiols, carboxy groups, alkoxycarbonyl groups having 1 to 4 carbon atoms, acyloxy groups having 1 to 5 carbon atoms, acylthio groups having 1 to 5 carbon atoms, and 1 to 5 carbon atoms Substituted by an acylamino group, cyano group or trifluoromethyl group; B D is hydrogen or an aliphatic hydrocarbon group having 1 to 4 carbon atoms; X D is S, O or SO; Y D is an aliphatic hydrocarbon group having 1 to 6 carbon atoms (where at least one hydrogen is a carboxyl group, COOR1 (where R1 is a substituted or unsubstituted alkyl or alkenyl group having 1 to 4 carbon atoms), CONR2R3 (where R2 and R3, respectively) May be the same as or different from each other, and each independently hydrogen or an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, COW (where W is a carboxyl group or group derived therefrom or an amino group or group derived therefrom) Ring or a heterocyclic ring which may be substituted), NR4R5 (wherein R4 and R5 may each be the same or different, each independently represent hydrogen, unsubstituted or substituted alkyl or C1-5 unsubstituted or OR 6 (where R 6 is hydrogen, unsubstituted or substituted alkyl group of 1 to 4 carbon atoms or unsubstituted or substituted acyl of 1 to 5 carbon atoms) Group); Z D is a carboxyl group, COOR7 (where R7 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), CONR8R9 (where R8 and R9 may be the same or different, respectively, and are each independently hydrogen or 1 to 4 carbon atoms) Unsubstituted or substituted alkyl group, cyano group, CH 2 OR10 (where R10 is hydrogen, unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or unsubstituted or substituted acyl group having 1 to 5 carbon atoms) , Hydroxy group, OCOR11 (where R11 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), NR12R13 (where R12 and R13 may each be the same or different, and are each independently hydrogen, unsubstituted 1 to 4 carbon atoms) Or a substituted alkyl group, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms), 5-tetrazolyl, chlorine, fluorine or hydrogen. 33) The ketone derivative of the general formula [1D] according to the above 1), or a pharmacologically acceptable salt thereof, as defined in the above 32), wherein: In the general formula [1D] above, A D is an unsubstituted or substituted benzene ring, and when substituted, hydrogen of 1 to 3 is substituted by methyl group, methoxy group, methoxycarbonyl group, nitro group, cyano group, halogen or trifluoromethyl group; B D is hydrogen or an alkyl group having 1 to 4 carbon atoms; X D is S; Y D is an aliphatic hydrocarbon group of 1 to 6 carbon atoms (where at least two hydrogens are carboxyl groups, COOR1 '(where R1' is an alkyl or alkenyl group of 1 to 4 carbon atoms), NHCOR14 (where R14 is hydrogen fluorine) Optionally substituted with a C1-4 alkyl group), a hydroxy group, or OCOR15, where R15 is a C1-4 alkyl group; Z D is a carboxy group, COOR7 '(where R7' is an alkyl group having 1 to 4 carbon atoms), or CH 2 OR10 '(where R10' is an acyl group having 1 to 5 carbon atoms). 34) The ketone derivative of the general formula [1D] according to item 33), or a pharmacologically acceptable salt thereof, as defined in the above 33), wherein: In the general formula [1D] above, A D is an unsubstituted benzene ring or a benzene ring substituted with a methyl group or a methoxy group; B D is hydrogen; X D is S; Y D is 2-acetylamino-2-carboxyethyl, 2-acetylamino-2-methoxycarbonylethyl or 2-acetylaminoethyl; Z D is a carboxy group, methoxycarbonyl group, acetoxymethyl group or hydroxymethyl group. 35) The ketone derivative of the general formula [1D] according to 1) above, or a pharmacologically acceptable salt thereof, as defined in 1) above: In the general formula [1D] above, A D and B D are joined together to form an unsubstituted or substituted cycloalkane-1-one ring having 3 to 7 carbon atoms (excluding 5 carbon atoms); X D is S, O or SO; Y D is an aliphatic hydrocarbon group having 1 to 6 carbon atoms, wherein at least one hydrogen is substituted with a carboxyl group or a group derived therefrom, an amino group or a group derived therefrom or a hydroxy group or a group derived therefrom; Z D is a carboxyl group or group derived therefrom, an unsubstituted or substituted alkyl group or alkenyl group, hydroxy group or group derived therefrom, an amino group or a group derived therefrom, a monocyclic aromatic heterocycle, a halogen having 1 to 4 carbon atoms Or hydrogen. 36) The ketone derivative of the general formula [1D] according to item 1) above, or a pharmacologically acceptable salt thereof, as defined in the above item 35): In the general formula [1D] above, A D and B D are joined together to form an unsubstituted or substituted cyclobutan-1-one ring or cyclohexan-1-one ring; X D is S, O or SO; Y D is an aliphatic hydrocarbon group having 1 to 6 carbon atoms (where at least one hydrogen is a carboxyl group, COOR1 (where R1 is a substituted or unsubstituted alkyl or alkenyl group having 1 to 4 carbon atoms), CONR2R3 (where R2 and R3, respectively) May be the same as or different from each other, and each independently hydrogen or an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, COW (where W is a carboxyl group or group derived therefrom or an amino group or group derived therefrom) Ring or a heterocyclic ring which may be substituted), NR4R5 (wherein R4 and R5 may each be the same or different, each independently represent hydrogen, unsubstituted or substituted alkyl or C1-5 unsubstituted or OR 6 (where R 6 is hydrogen, unsubstituted or substituted alkyl group of 1 to 4 carbon atoms or unsubstituted or substituted acyl of 1 to 5 carbon atoms) Group); Z D is a carboxyl group, COOR7 (where R7 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), CONR8R9 (where R8 and R9 may be the same or different, respectively, and are each independently hydrogen or 1 to 4 carbon atoms) Unsubstituted or substituted alkyl group, cyano group, CH 2 OR10 (where R10 is hydrogen, unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or unsubstituted or substituted acyl group having 1 to 5 carbon atoms) , Hydroxy group, OCOR11 (where R11 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), NR12R13 (where R12 and R13 may each be the same or different, and are each independently hydrogen, unsubstituted 1 to 4 carbon atoms) Or a substituted alkyl group, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms), 5-tetrazolyl, chlorine, fluorine or hydrogen. 37) The ketone derivative of the general formula [1D] as described in 1) above, or a pharmacologically acceptable salt thereof, as defined in the above 36), wherein: In the general formula [1D] above, A D and B D are joined together to form a cyclobutan-1-one ring or a cyclohexan-1-one ring; X D is S; Y D is an aliphatic hydrocarbon group of 1 to 6 carbon atoms (where at least two hydrogens are carboxyl groups, COOR1 '(where R1' is an alkyl or alkenyl group of 1 to 4 carbon atoms), NHCOR14 (where R14 is hydrogen fluorine) Optionally substituted with a C1-4 alkyl group), a hydroxy group, or OCOR15, where R15 is a C1-4 alkyl group; Z D is a carboxy group, COOR7 '(where R7' is an alkyl group having 1 to 4 carbon atoms), or CH 2 OR10 '(where R10' is an acyl group having 1 to 5 carbon atoms). 38) The ketone derivative of the general formula [1D] or the pharmacologically acceptable salt thereof according to the above 37), wherein the ketone derivative of the general formula [1D] according to the above 1) is defined as follows: In the general formula [1D] above, (I) A D and B D combine together to form a cyclobutan-1-one ring, X D is S, Y D is 2-acetylamino-2-carboxyethyl, and Z D is a carboxy group; (II) A D and B D join together to form a cyclobutan-1-one ring, X D is S, Y D is 2-acetylamino-2-methoxycarbonyl group ethyl, and Z D is a methoxycarbonyl group ego; (III) A D and B D combine together to form a cyclobutan-1-one ring, X D is S, Y D is 2,3-dihydroxy-n-propyl, and Z D is acetoxymethyl ego; (IV) A D and B D are bonded together to form a cyclobutan-1-one ring, X D is S, Y D is 2-acetylamino-2-carboxyethyl, and Z D is a carboxy group. 39) The β-di-substituted aminoketone derivative of the general formula [1F] according to the above 1), or a pharmacologically acceptable salt thereof, according to 1) above, which is defined as follows: In the above general formula [1F], A F is an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 4 carbon atoms; B F is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 4 carbon atoms; X F and Y F are linear or branched aliphatic hydrocarbon groups having 1 to 10 carbon atoms, wherein at least one hydrogen is a carboxyl group or a group derived therefrom, an amino group or a group derived therefrom, or a hydroxy group or derived therefrom May be optionally substituted with a group, or X F and Y F are bonded directly to each other or through a hetero atom to form a monocyclic hetero ring (where at least one hydrogen is an alkyl group having 1 to 4 carbon atoms, a phenyl group or a carboxyl group) Or may be optionally substituted with a group derived therefrom, an amino group or a group derived therefrom, or a hydroxy group or a group derived therefrom; Z F is a carboxyl group or a group derived therefrom, an unsubstituted or substituted alkyl or alkenyl group, a hydroxy group or a group derived therefrom, an amino group or a group derived therefrom, a monocyclic aromatic heterocycle or a halogen having 1 to 4 carbon atoms to be. 40) The β-di-substituted aminoketone derivative of the general formula [1F] according to the above 1), or a pharmacologically acceptable salt thereof, as defined in the above 39), as defined below: In the above general formula [1F], A F is an unsubstituted or substituted methyl group, ethyl group, n-propyl group or isopropyl group; B F is hydrogen; X F and Y F may be the same as or different from each other, and each independently represent an alkyl group having 1 to 6 carbon atoms, or X F and Y F are bonded directly to each other or through a hetero atom, and have 1 to 4 carbon atoms. A monocyclic hetero ring which may be unsubstituted or substituted with an alkyl group or a phenyl group of; Z F is a carboxy group, COOR1 (where R1 is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a phenyl group), CONR2R3 (where R2 and R3 may be the same or different, respectively, independently hydrogen or carbon atoms 1 to 4 represents an unsubstituted or substituted alkyl group, a cyano group, CH 2 OR4 (wherein R4 is hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms) Hydroxy group, OR5 (where R5 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms), NR6R7 (where R6 and R7 are each the same or May be different from each other and independently represent hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms), 5-tetrazolyl, chlorine or fluorine. 41) The β-di-substituted aminoketone derivative of the general formula [1F] according to the above 1), or a pharmacologically acceptable salt thereof, as defined in the above 40) as defined below: In the above general formula [1F], A F is a methyl group; B F is hydrogen; X F and Y F are both ethyl, n-propyl or isopropyl groups, and X F and Y F are bonded directly to each other or through a hetero atom to form pyrrolidine, piperidine, morpholine, 4-methylpipe To form a lazine or 4-phenylpiperazine ring; Z F is a carboxy group, COOR1 '(where R1' is an alkyl group having 1 to 4 carbon atoms), CONR2'R3 '(where R2' and R3 'may be the same or different and are each hydrogen or an alkyl group having 1 to 4 carbon atoms) ) Or cyano group. 42) The β-di-substituted aminoketone derivative of the general formula [1F] according to 1) above, or a pharmacologically acceptable salt thereof, as defined in the above 1), wherein: In the above general formula [1F], A F is an unsubstituted or substituted aryl group, heteroaryl group, or saturated heterocycle; B F is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 4 carbon atoms; X F and Y F are linear or branched aliphatic hydrocarbon groups having 1 to 10 carbon atoms, wherein at least one hydrogen is a carboxyl group or a group derived therefrom, an amino group or a group derived therefrom, or a hydroxy group or derived therefrom May be optionally substituted with a group) or X F and Y F are bonded directly to each other or through a hetero atom to form a hetero ring (where at least one hydrogen is an alkyl group having 1 to 4 carbon atoms, a phenyl group, a carboxyl group or from Optionally substituted with a derived group, an amino group or a group derived therefrom, or a hydroxy group or a group derived therefrom); Z F is a carboxyl group or a group derived therefrom, an unsubstituted or substituted alkyl or alkenyl group, a hydroxy group or a group derived therefrom, an amino group or a group derived therefrom, a monocyclic aromatic heterocycle or a halogen having 1 to 4 carbon atoms to be. 43) The β-di-substituted aminoketone derivative of the general formula [1F] as described in 1) above, or a pharmacologically acceptable salt thereof, as defined in the above 42): In the above general formula [1F], A F is an unsubstituted or substituted benzene ring or a monocyclic aromatic heterocyclic heterocycle; B F is hydrogen; X F and Y F may be the same or different and are a straight or branched aliphatic hydrocarbon group having 1 to 6 carbon atoms, or X F and Y F are bonded directly to each other or through a hetero atom, and have 1 to 1 carbon atoms. To form a substituted or unsubstituted heterocyclic alkyl group or phenyl group of 4; Z F is a carboxy group, COOR1 (where R1 is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a phenyl group), CONR2R3 (where R2 and R3 may be the same or different, respectively, independently hydrogen or carbon atoms 1 to 4 represents an unsubstituted or substituted alkyl group, a cyano group, CH 2 OR4 (wherein R4 is hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms) Hydroxy group, OR5 (where R5 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms), NR6R7 (where R6 and R7 are each the same or May be different from each other and independently represent hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms), 5-tetrazolyl, chlorine or fluorine. 44) The β-di-substituted aminoketone derivative of the general formula [1F] according to the above 1), or a pharmacologically acceptable salt thereof, as defined in the above 43) as defined below: In the above general formula [1F], A F is an unsubstituted or substituted benzene ring, and when substituted, a hydrogen atom of 1 to 3 is an alkyl group having 1 to 4 carbon atoms, a halogen, a hydroxyl group, an alkoxy group having 1 to 4 carbon atoms, an amino group or a carbon atom having 1 to 3 carbon atoms. 4 alkyl- or dialkylamino groups, thiols, carboxyl groups, alkoxycarbonyl groups having 1 to 4 carbon atoms, acyloxy groups having 1 to 5 carbon atoms, acylthio groups having 1 to 5 carbon atoms, and acylamino groups having 1 to 5 carbon atoms Substituted by a cyano group or a trifluoromethyl group; B F is hydrogen; X F and Y F are good even if each the same or different, or alkyl groups of carbon atoms 1 to 6, or X F is and Y F are directly bonded to each other or bonded through a hetero atom to the carbon atom alkyl group or a phenyl group of atoms from 1 to 4 To form a substituted or unsubstituted heterocycle; Z F is a carboxy group, COOR1 '(where R1' is an alkyl group having 1 to 4 carbon atoms), CONR2'R3 '(where R2' and R3 'may be the same or different, respectively, hydrogen or each of 1 to 4 carbon atoms). An alkyl group), a cyano group, and CH 2 OR4 '(where R4' is hydrogen, an alkyl group having 1 to 4 carbon atoms or an acyl group having 1 to 5 carbon atoms). 45) The β-di-substituted aminoketone derivative of the general formula [1F] according to the above 1), as defined in the above 44), or a pharmacologically acceptable salt thereof: In the above general formula [1F], A F is an unsubstituted or substituted benzene ring, in which, when substituted, one to three hydrogen atoms are substituted with a methyl group, a methoxy group, a methoxycarbonyl group, a nitro group, a cyano group, a halogen or a trifluoromethyl group; B F is hydrogen; X F and Y F are both ethyl groups, n-propyl groups, or isopropyl groups, or X F and Y F are directly bonded to each other or through a hetero atom to form pyrrolidine, piperidine, morpholine, 4 -Form methylpiperazine or 4-phenylpiperazine ring; Z F is a carboxy group, COOR1 '' (where R1 '' is a methyl group or ethyl group), CONR2''R3 '' (where R2 '' and R3 '' may be the same or different and are each hydrogen, methyl or ethyl group) Or cyano group. 46) The β-di-substituted aminoketone derivative of the general formula [1F] according to 1) above, or a pharmacologically acceptable salt thereof, as defined in 1) above: In the above general formula [1F], A F and B F are bonded together to form an unsubstituted or substituted cycloalkane-1-one ring having 3 to 7 carbon atoms, or A F and B F are bonded together to form a carbon atom fused with an aromatic hydrocarbon or aromatic heterocycle. A cycloalkane-1-one ring of embroidery 3 to 7 is formed; X F and Y F are linear or branched aliphatic hydrocarbon groups having 1 to 10 carbon atoms, wherein at least one hydrogen is a carboxyl group or a group derived therefrom, an amino group or a group derived therefrom, or a hydroxy group or derived therefrom May be optionally substituted with a group, or X F and Y F are bonded directly to each other or through a hetero atom to form a hetero ring (where at least one hydrogen is an alkyl group having 1 to 4 carbon atoms, a phenyl group, a carboxyl group or Optionally substituted with a group derived from, an amino group or a group derived therefrom, or a hydroxy group or a group derived therefrom); Z F is a carboxyl group or a group derived therefrom, an unsubstituted or substituted alkyl or alkenyl group, a hydroxy group or a group derived therefrom, an amino group or a group derived therefrom, a monocyclic aromatic heterocycle or a halogen having 1 to 4 carbon atoms to be. 47) The β-di-substituted aminoketone derivative of the general formula [1F] as described in 1) above, or a pharmacologically acceptable salt thereof, as defined in the above 46), wherein: In the above general formula [1F], A F and B F are bonded together to form an unsubstituted or substituted cycloalkane-1-one ring having 4 to 6 carbon atoms, or an unsubstituted 4 to 6 carbon atoms fused with an aromatic hydrocarbon or a monocyclic aromatic heterocycle, or To form a substituted cycloalkane-1-one ring; Each of X F and Y F may be the same or different and independently represents a linear or branched aliphatic hydrocarbon group having 1 to 6 carbon atoms, or X F and Y F are directly bonded to each other or through a hetero atom To form a monocyclic heterocyclic ring (which may be unsubstituted or substituted with an alkyl group having 1 to 4 carbon atoms or a phenyl group); Z F is a carboxy group, COOR1 (where R1 is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a phenyl group), CONR2R3 (where R2 and R3 may be the same or different, respectively, independently hydrogen or carbon atoms 1 to 4 represents an unsubstituted or substituted alkyl group, a cyano group, CH 2 OR4 (wherein R4 is hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms) Hydroxy group, OR5 (where R5 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms, preferably an alkyl group having 1 to 4 carbon atoms or NR6R7 (where each of R6 and R7 may be the same or different, and are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or an acyl group having 1 to 5 carbon atoms), 5-tetrazolyl, Chlorine or fluorine. 48) The β-di-substituted aminoketone derivative of the general formula [1F] according to the above 1), or a pharmacologically acceptable salt thereof, as defined in the above 47), as defined below: In the above general formula [1F], A F and B F combine together to form an unsubstituted or substituted cyclobutan-1-one ring, or an unsubstituted or substituted cyclopentan-1-one ring fused with benzene or a monocyclic aromatic heterocycle; Each of X F and Y F may be the same or different and independently represents an alkyl group having 1 to 6 carbon atoms, or X F and Y F are each directly bonded to each other or through a hetero atom to form an alkyl group having 1 to 4 carbon atoms. Or a monocyclic hetero ring which may be unsubstituted or substituted with a phenyl group; Z F is a carboxy group, COOR1 '(where R1' is an alkyl group having 1 to 4 carbon atoms), CONR2'R3 '(where R2' and R3 'may be the same or different, respectively, hydrogen or carbon atoms having 1 to 4 atoms, respectively An alkyl group), a cyano group, or CH 2 OR4 '(where R4' is hydrogen, an alkyl group having 1 to 4 carbon atoms or an acyl group having 1 to 5 carbon atoms). 49) The β-di-substituted aminoketone derivative of the general formula [1F] according to the above 1), or a pharmacologically acceptable salt thereof, as defined in the above 48) as defined below: In the above general formula [1F], A F and B F join together to form a cyclobutan-1-one ring or indan-1-one ring; X F and Y F are both ethyl, n-propyl, or isopropyl groups, or X F and Y F are bonded directly to each other or through a hetero atom to form pyrrolidine, piperidine, morpholine, 4 -Form methylpiperazine or 4-phenylpiperazine ring; Z F is a carboxy group, COOR1 '' (where R1 '' is a methyl or ethyl group), CONR2''R3 '' (where R2 '' and R3 '' may be the same or different and are each hydrogen, methyl or ethyl group) Or cyano group. 50) The cyclopentanone derivative of the general formula [1A] according to the above 1), or any one of the above 2) to 6), which further includes the definitions of (1) to (7) below. A pharmaceutical composition containing a cyclopentanone derivative or a pharmacologically acceptable salt thereof as an active ingredient: (1) when Z1 A and Z2 A are hydrogen, X A is S, Y A is a methyl group or benzyl group, Z3 A is a methoxycarbonyl group, (2) when Z1 A and Z2 A are hydrogen, X A is O or N, Y A is a benzyl group, Z3 A is a carboxy group, methoxycarbonyl group or ethoxycarbonyl group, (3) X A is N or O, Z 1 A and Z 3 A are hydrogen, Z 2 A is a carboxy group, methoxycarbonyl group, (4) X A is O, Z 1 A is a hydroxyl group or a group derived therefrom, Z 2 A is a hydrogen, Z 3 A is an amino group or a group derived therefrom, (5) X A is S, Y1 A is a phenyl group, Z1 A is a dimethoxymethyl group, Z2 A and Z3 A are hydrogen, (6) X A is O, Y 1 A is a methyl group, Z 1 A is a 1-methoxy-1-phenylthiomethyl group, Z 2 A and Z 3 A are hydrogen, (7) Z 1 A is S, SO or SO 2 , Z 2 A is a hydroxy group or a group derived therefrom, Z 3 A is hydrogen. 51) The cyclopentanone derivative of the general formula [1A] according to the above 1), or any one of the above 2) to 6), which further includes the definitions of (1) to (7) below. A composition for the treatment of central nervous system, comprising a cyclopentanone derivative, or a pharmacologically acceptable salt thereof as an active ingredient: (1) when Z1 A and Z2 A are hydrogen, X A is S, Y A is a methyl group or benzyl group, Z3 A is a methoxycarbonyl group, (2) when Z1 A and Z2 A are hydrogen, X A is O or N, Y A is a benzyl group, Z3 A is a carboxy group, methoxycarbonyl group or ethoxycarbonyl group, (3) X A is N or O, Z 1 A and Z 3 A are hydrogen, Z 2 A is a carboxy group, methoxycarbonyl group, (4) X A is O, Z 1 A is a hydroxyl group or a group derived therefrom, Z 2 A is a hydrogen, Z 3 A is an amino group or a group derived therefrom, (5) X A is S, Y1 A is a phenyl group, Z1 A is a dimethoxymethyl group, Z2 A and Z3 A are hydrogen, (6) X A is O, Y 1 A is a methyl group, Z 1 A is a 1-methoxy-1-phenylthiomethyl group, Z 2 A and Z 3 A are hydrogen, (7) Z 1 A is S, SO or SO 2 , Z 2 A is a hydroxy group or a group derived therefrom, Z 3 A is hydrogen. 52) The cyclopentanone derivative of the general formula [1A] according to the above 1), or any one of the above 2) to 6), further including the definitions of (1) to (7) below. A composition for treating peripheral neuropathy, comprising a cyclopentanone derivative, or a pharmacologically acceptable salt thereof, as an active ingredient: (1) when Z1 A and Z2 A are hydrogen, X A is S, Y A is a methyl group or benzyl group, Z3 A is a methoxycarbonyl group, (2) when Z1 A and Z2 A are hydrogen, X A is O or N, Y A is a benzyl group, Z3 A is a carboxy group, methoxycarbonyl group or ethoxycarbonyl group, (3) X A is N or O, Z 1 A and Z 3 A are hydrogen, Z 2 A is a carboxy group, methoxycarbonyl group, (4) X A is O, Z 1 A is a hydroxyl group or a group derived therefrom, Z 2 A is a hydrogen, Z 3 A is an amino group or a group derived therefrom, (5) X A is S, Y1 A is a phenyl group, Z1 A is a dimethoxymethyl group, Z2 A and Z3 A are hydrogen, (6) X A is O, Y 1 A is a methyl group, Z 1 A is a 1-methoxy-1-phenylthiomethyl group, Z 2 A and Z 3 A are hydrogen, (7) Z 1 A is S, SO or SO 2 , Z 2 A is a hydroxy group or a group derived therefrom, Z 3 A is hydrogen. 53) The cyclopentanone derivative of the general formula [1A] according to the above 1), or any one of the above 2) to 6), which further includes the definitions of (1) to (7) below. A composition for promoting neuronal differentiation, comprising a cyclopentanone derivative, or a pharmacologically acceptable salt thereof as an active ingredient: (1) when Z1 A and Z2 A are hydrogen, X A is S, Y A is a methyl group or benzyl group, Z3 A is a methoxycarbonyl group, (2) when Z1 A and Z2 A are hydrogen, X A is O or N, Y A is a benzyl group, Z3 A is a carboxy group, methoxycarbonyl group or ethoxycarbonyl group, (3) X A is N or O, Z 1 A and Z 3 A are hydrogen, Z 2 A is a carboxy group, methoxycarbonyl group, (4) X A is O, Z 1 A is a hydroxyl group or a group derived therefrom, Z 2 A is a hydrogen, Z 3 A is an amino group or a group derived therefrom, (5) X A is S, Y1 A is a phenyl group, Z1 A is a dimethoxymethyl group, Z2 A and Z3 A are hydrogen, (6) X A is O, Y 1 A is a methyl group, Z 1 A is a 1-methoxy-1-phenylthiomethyl group, Z 2 A and Z 3 A are hydrogen, (7) Z 1 A is S, SO or SO 2 , Z 2 A is a hydroxy group or a group derived therefrom, Z 3 A is hydrogen. 54) 2,3-di-substituted cyclopentanone derivatives of the general formula [1B] according to 1) above or 2,3-di-substituted cyclopentanone according to any one of 7) to 18) above. A pharmaceutical composition comprising a derivative or a pharmacologically acceptable salt thereof as an active ingredient. 55) 2,3-di-substituted cyclopentanone derivatives of the general formula [1B] according to 1) or 2,3-di-substituted cyclopentanone according to any one of 7) to 18) above. A composition for the treatment of central nervous disorders containing a derivative or a pharmacologically acceptable salt thereof as an active ingredient. 56) 2,3-di-substituted cyclopentanone derivatives of the general formula [1B] according to 1) above or 2,3-di-substituted cyclopentanone according to any one of 7) to 18) above. A composition for treating peripheral neuropathy, comprising a derivative or a pharmacologically acceptable salt thereof as an active ingredient. 57) 2,3-di-substituted cyclopentanone derivatives of the general formula [1B] according to 1) above or 2,3-di-substituted cyclopentanone according to any one of 7) to 18) above. A composition for promoting neuronal differentiation comprising a derivative or a pharmacologically acceptable salt thereof as an active ingredient. 58) A cyclopentanone derivative of the general formula [1C] according to 1) above or a cyclopentanone derivative according to any one of 19) to 26) above, or a pharmacologically acceptable salt thereof, wherein X C When is O or NH, Z1 C and Z3 C is hydrogen, Z2 C further comprises a hydrogen or a hydroxyl group or a group derived therefrom, the pharmaceutical composition containing the cyclopentanone derivative as an active ingredient. 59) As the cyclopentanone derivative of the general formula [1C] according to 1) or the cyclopentanone derivative according to any one of 19) to 26), or a pharmacologically acceptable salt thereof, X C When is O or NH, Z1 C and Z3 C is hydrogen, Z2 C is a central nervous system disorder containing the cyclopentanone derivative as an active ingredient, further comprising the case of hydrogen or a hydroxyl group or a group derived therefrom Composition for treatment. 60) A cyclopentanone derivative of the general formula [1C] according to 1) or a cyclopentanone derivative according to any one of 19) to 26), or a pharmacologically acceptable salt thereof, wherein X C Is O or NH, Z 1 C and Z 3 C are hydrogen, and Z 2 C is a peripheral neuropathy containing the cyclopentanone derivative as an active ingredient, further comprising the case of hydrogen or a hydroxyl group or a group derived therefrom. Composition for treatment. 61) A cyclopentanone derivative of the general formula [1C] according to 1) above, or a cyclopentanone derivative according to any one of 19) to 26) above, or a pharmacologically acceptable salt thereof, wherein X C Is O or NH, Z1 C and Z3 C are hydrogen, and Z2 C is hydrogen cell differentiation containing the cyclopentanone derivative as an active ingredient, further comprising the case of hydrogen or a hydroxyl group or a group derived therefrom. Composition for promotion. 62) Ketone derivative of the general formula [1D] according to the above 1) or the ketone derivative according to any one of the above 26) to 38), further including the definitions of (1) to (4) below. Or a pharmacologically acceptable salt thereof as an active ingredient: When A D and B D are bonded together to form a cyclobutane ring, the ketone derivative is (1) X D is O, Y D is a methyl group, n-octyl group or n-hexadecyl group, and Z D is a methoxycarbonyl group; (2) X D is O, Y D is a benzyl group, and Z D is a benzyloxymethyl group; (3) X D is O, Y D is p-methoxybenzyl group, and Z D is p-methoxybenzyloxymethyl group; (4) When X D is O, Y D is a trityl group, Z D is a trityloxymethyl group, and A D is an unsubstituted benzene ring and B D is hydrogen, X D is S, Y D is a methyl group, an ethyl group Or isopropyl group and Z D is a carboxy group. 63) The ketone derivative of the general formula [1D] according to the above 1), or the ketone derivative according to any one of the above 26) to 38), further including the definitions of (1) to (4) below. Or a pharmacologically acceptable salt thereof as an active ingredient, a composition for treating central nervous system disorders: When A D and B D are bonded together to form a cyclobutane ring, the ketone derivative is (1) X D is O, Y D is a methyl group, n-octyl group or n-hexadecyl group, and Z D is a methoxycarbonyl group; (2) X D is O, Y D is a benzyl group, and Z D is a benzyloxymethyl group; (3) X D is O, Y D is p-methoxybenzyl group, and Z D is p-methoxybenzyloxymethyl group; (4) When X D is O, Y D is a trityl group, Z D is a trityloxymethyl group, and A D is an unsubstituted benzene ring and B D is hydrogen, X D is S, Y D is a methyl group, an ethyl group Or isopropyl group and Z D is a carboxy group. 64) The ketone derivative of the general formula [1D] according to the above 1), or the ketone derivative according to any one of the above 26) to 38), further including the definitions of (1) to (4) below. Or a pharmacologically acceptable salt thereof as an active ingredient, a composition for treating peripheral neuropathy: When A D and B D are bonded together to form a cyclobutane ring, the ketone derivative is (1) X D is O, Y D is a methyl group, n-octyl group or n-hexadecyl group, and Z D is a methoxycarbonyl group; (2) X D is O, Y D is a benzyl group, and Z D is a benzyloxymethyl group; (3) X D is O, Y D is p-methoxybenzyl group, and Z D is p-methoxybenzyloxymethyl group; (4) When X D is O, Y D is a trityl group, Z D is a trityloxymethyl group, and A D is an unsubstituted benzene ring and B D is hydrogen, X D is S, Y D is a methyl group, an ethyl group Or isopropyl group and Z D is a carboxy group. 65) The ketone derivative of the general formula [1D] according to the above 1), or the ketone derivative according to any one of the above 26) to 38), further including the definitions of (1) to (4) below. Or a pharmacologically acceptable salt thereof as an active ingredient, a composition for promoting neuronal differentiation: When A D and B D are bonded together to form a cyclobutane ring, the ketone derivative is (1) X D is O, Y D is a methyl group, n-octyl group or n-hexadecyl group, and Z D is a methoxycarbonyl group; (2) X D is O, Y D is a benzyl group, and Z D is a benzyloxymethyl group; (3) X D is O, Y D is p-methoxybenzyl group, and Z D is p-methoxybenzyloxymethyl group; (4) When X D is O, Y D is a trityl group, Z D is a trityloxymethyl group, and A D is an unsubstituted benzene ring and B D is hydrogen, X D is S, Y D is a methyl group, an ethyl group Or isopropyl group and Z D is a carboxy group. 66) A pharmaceutical composition containing a compound of the general formula [1E] or a pharmacologically acceptable salt thereof as an active ingredient according to the above 1). 67) A composition for the treatment of central nervous disorders, comprising as an active ingredient a compound of the general formula [1E] or a pharmacologically acceptable salt thereof according to item 1). 68) A composition for treating peripheral neuropathy comprising a compound of formula [1E] or a pharmacologically acceptable salt thereof as an active ingredient according to item 1). 69) A composition for promoting neuronal differentiation containing a compound of formula [1E] or a pharmacologically acceptable salt thereof as an active ingredient according to item 1) above. 70) β-di-substituted aminoketone derivative of the general formula [1F] according to 1) above or β-di-substituted aminoketone derivative according to any one of 39) to 49) above, or pharmacologically As the acceptable salt, when A F is an unsubstituted benzene ring, the β-di-substituted aminoketone derivative is B F is hydrogen, X F is directly bonded to Y F to form a piperidine ring, and Z F A pharmaceutical composition comprising as an active ingredient the β-di-substituted aminoketone derivative or a pharmacologically acceptable salt thereof further comprising those having a carboxy group. 71) β-di-substituted aminoketone derivative of the general formula [1F] according to 1) above or β-di-substituted aminoketone derivative according to any one of 39) to 49) above, or pharmacologically As the acceptable salt, when A F is an unsubstituted benzene ring, the β-di-substituted aminoketone derivative is B F is hydrogen, X F is directly bonded to Y F to form a piperidine ring, and Z F Is a carboxy group, further comprising the β-di-substituted amino ketone derivative or a pharmacologically acceptable salt thereof as a active ingredient containing a composition for the treatment of central nervous system. 72) β-di-substituted aminoketone derivative of the general formula [1F] according to 1) above, or β-di-substituted aminoketone derivative according to any one of 39) to 49) above, or pharmacologically As the acceptable salt, when A F is an unsubstituted benzene ring, the β-di-substituted aminoketone derivative is B F is hydrogen, X F is directly bonded to Y F to form a piperidine ring, and Z F Is a carboxy group, further comprising the β-di-substituted amino ketone derivative or a pharmacologically acceptable salt thereof as an active ingredient, a composition for treating peripheral neuropathy. 73) β-di-substituted aminoketone derivative of the general formula [1F] according to 1) above or β-di-substituted aminoketone derivative according to any one of 39) to 49) above, or pharmacologically As the acceptable salt, when A F is an unsubstituted benzene ring, the β-di-substituted aminoketone derivative is B F is hydrogen, X F is directly bonded to Y F to form a piperidine ring, and Z F Is a carboxy group, further comprising a β-di-substituted amino ketone derivative or a pharmacologically acceptable salt thereof as a composition for promoting neuronal differentiation. Next, a method for preparing a compound of the present invention and a pharmacologically acceptable salt thereof and an action of promoting cell differentiation will be described in more detail with reference to the following Examples. Example 1: Preparation of 4-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-3-oxo-1-cyclopentanecarboxylic acid (Compound 1A) (1) 1,1-dimethoxy-2,4-bis (methoxycarbonyl) cyclopentane (Compound 1A-B) and 1,1-dimethoxy-2,3-bis (methoxycarbonyl) cyclopentane Preparation of (Compound 1A-b) 2,4-bis (methoxycarbonyl) cyclopentanone (Compound 1A-A), see J. Chem. Org. Chem., 47, 2379 (1982), as a mixture with 2,3-bis (methoxycarbonyl) cyclopentanone (Compound 1-Aa). These two compounds can be separated from each other by silica gel column chromatography by converting this mixture into 2,4-bis (hydroxymethyl) cyclopentanone and 2,3-bis (hydroxymethyl) cyclopentanone. . To a mixture of compound (1A-A) and compound (1A-a) (6970 mg, 34.85 mmol) was added methanol anhydrous (35 ml), methyl orthoformate (4.74 ml) and p-paratoluenesulfonic acid monohydrate (165 mg). It was added and the mixture was stirred at room temperature for 18 hours. Toluene (60 ml) was added to the reaction mixture, which was then washed twice with saturated sodium hydrogen carbonate solution (25 ml). The toluene layer was washed with saturated aqueous sodium chloride solution (50 ml), concentrated to 1,1-dimethoxy-2,4-bis (methoxycarbonyl) cyclopentane (Compound 1A-B) and 1,1-dimethoxy A mixture (8334 mg, yield: 97.2%) of -2,3-bis (methoxycarbonyl) cyclopentane (Compound 1A-b) was obtained. (2) Preparation of 2,4-bis (hydroxymethyl) cyclopentanone (Compound 1A-C) A solution of compound (1A-B) and a mixture of compounds (1A-b) (9676 mg, 39.32 mmol) was added to anhydrous ether (10 ml) to give a solution of anhydrous ether of lithium aluminum hydride (3120 mg) (43 ml) Was added dropwise under ice cooling for 1 hour. After stirring for 30 minutes, water (3.12 ml), 15% sodium hydroxide (3.12 ml) and water (3.12 ml) were further added to the mixture, followed by stirring for 30 minutes. Anhydrous sodium sulfate (10 g), ether (55 ml) and HAIFURO SUPER CEL (6 g) were added to the mixture, and the mixture was stirred for 30 minutes and then the mixture was filtered. The residue was extracted twice with ether (100 ml). All ethereal fractions were recovered and concentrated. The obtained residue was dissolved in acetone (37 ml), and water (1.85 ml) and 1N hydrochloric acid (1.85 ml) were added to the solution, and the mixture was stirred at room temperature for 30 minutes. 1N sodium hydroxide (1.85 ml) was added to the reaction mixture followed by silica gel (18 g) and then concentrated. The residue was purified by silica gel column chromatography (550 ml, dichloromethane: methanol = 30: 1) to give compound (1A-C, 1310 mg, yield: 23.1%) and compound (1A-c, 1539 mg, yield : 27.0%). TLC (silica gel: chloroform: methanol = 10: 1): Compound (1A-C, Rf = 0.42), Compound (1A-c, Rf = 0.45) (3) Preparation of 2,4-bis (acetoxymethyl) cyclopentanone (Compound 1A-D) Anhydrous pyridine (4 ml) and acetic anhydride (4 ml) were added to compound (1A-C) (1130 mg, 7.847 mmol), and the mixture was stirred at room temperature for 1 hour. After concentration of the reaction mixture, the residue was purified by silica gel column chromatography (150 ml, hexanes: ethyl acetate = 1: 1) to give compound (1A-D) (1598 mg, yield: 89.2%). (4) Preparation of 4-acetoxymethyl-2-{(2,3-dihydroxy) propylthio} methylcyclopentanone (Compound 1A-E) Methanol (5 ml), acetone (30 ml) and 1N sodium hydroxide (6.1 ml) were added to compound (1A-D) (1.4 g, 133 mmol) and alpha-thioglycerine (0.66 g, 133 mmol) and this mixture Stirred for 45 minutes. 1N hydrochloric acid was added to the reaction solution to adjust pH to 7.0, and the mixture was concentrated. To the residue was added saturated aqueous sodium chloride solution (30 ml) and the mixture was extracted five times with dichloromethane (30 ml). The dichloromethane layer was dried over anhydrous sodium sulfate and then concentrated. The residue thus obtained was purified by silica gel column chromatography (300 ml, chloroform: methanol = 40: 1 to 10: 1) to give compound (1A-E) (1.5 g, yield: 88.23%). (5) Preparation of 4-acetoxymethyl-2-{(2,3-0-isopropylidene) propylthio} methylcyclopentanone (Compound 1A-F) To compound (1A-E) (1.6 g, 5.78 mmol) was added acetone (15 ml), dimethoxypropane (1.81 g, 17.34 mmol) and p-toluenesulfonic acid monohydrate (0.11 g, 0.578 mmol). The mixture was stirred at room temperature for 2 hours, after which water (20 ml) and ethyl acetate (80 ml) were added, and the pH of the aqueous phase was adjusted to 7.0 with saturated sodium bicarbonate. The aqueous phase was separated by addition of sodium chloride until saturated. The aqueous phase was extracted twice with ethyl acetate (50 ml) again. The ethyl acetate layer was taken, dried over anhydrous sodium sulfate and concentrated, and then the obtained residue was purified by silica gel column chromatography (300 ml, hexane: ethyl acetate = 3: 1) to give compound (1A-F) ( 1.6 g, yield: 87.4%). (6) Preparation of 4-hydroxymethyl-2-[(2,3-O-isopropylidene) propylthio] methylcyclopentanone (Compound 1A-G) Methanol (20 ml) and water (5 ml) were added to compound (1A-F) (1.6 g, 5.05 mmol), and 1N sodium hydroxide (3.2 ml, 3.20 mmol) was added to the mixture under ice cooling, followed by stirring for 1 hour. . After adjusting to pH 7.0 by adding 1N hydrochloric acid, the reaction solution was concentrated and saturated sodium chloride aqueous solution (15 ml) was added to the residue. After extraction three times with ethyl acetate (30 ml), the ethyl acetate layer was dried over anhydrous sodium sulfate and then concentrated to dryness. The residue was purified by silica gel column chromatography (250 ml, ethyl acetate: hexane = 2: 1) to give compound (1A-G) (1.0 g, yield: 72.4%). (7) Preparation of 4-hydroxymethyl-2-[(2,3-O-isopropylidene) propylsulfonyl] methylcyclopentanone (Compound 1A-H) Compound (1A-G) (1.0 g, 3.64 mmol) was dissolved in dichloromethane (25 ml), and the solution was diluted with four portions of m-chloroperbenzoic acid (1.74 g, 80% purity, 8.04 mmol) under ice-cooling. Was added. After stirring for 1.5 hours, the mixture was filtered, and water (10 ml), 20% sodium hydrogen sulfite (1 ml) and saturated sodium bicarbonate (2 ml) were added to the filtrate, and the mixture was stirred at room temperature for 15 minutes. A saturated aqueous sodium chloride solution (20 ml) was added to the reaction mixture to separate the mixture. The aqueous phase was extracted twice with dichloromethane (25 ml), then the dichloromethane layer was taken, dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (300 ml, ethyl acetate: hexane = 3: 1) to give compound (1A-H) (1.0 g, yield: 89.2%). (8) Preparation of 4-[(2,3-O-isopropylidene) propylsulfonyl] methyl-3-oxo-1-cyclopentanecarboxylic acid (compound a) Compound (1A-H) (1.0 g, 3.26 mmol) was dissolved in acetone (55 ml). Jones solution (2.5 ml) was added dropwise to this solution with cooling for 15 minutes under cooling. The reaction solution was kept orange while the reaction solution was stirred for 20 minutes. 2-propanol (1 ml) was added to the reaction mixture, which was stirred for 5 minutes and then concentrated. To the residue was added water (20 ml) and saturated aqueous sodium chloride solution (30 ml). The resulting mixture was extracted eight times with dichloromethane (40 ml). The dichloromethane layer was washed with saturated aqueous sodium chloride solution (200 ml), dried over anhydrous sodium sulfate and then concentrated. The residue was purified by silica gel column chromatography (100 ml, chloroform: methanol = 10: 1 to 4: 1) to give compound (a) (0.69 g, yield: 66.3%). (9) Preparation of 4-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-3-oxo-1-cyclopentanecarboxylic acid [Compound 1A] Compound (a) (170 mg, 0.53 mmol) was dissolved in acetone (7 ml) and N-acetyl-L-cysteine (87 mg, 0.53 mmol) and 1N sodium hydroxide (1.5 ml) were added to this solution. The mixture was stirred at room temperature for 2 hours. 1N hydrochloric acid was added to the reaction mixture to adjust the pH to 6.8, and then concentrated. The residue was purified by QAE-Sephadex (200 ml, Cl type, 0.05-0.4 M aqueous sodium chloride solution, 700 ml each, gradient elution) to afford the desired fractions. After concentrating this fraction, methanol (3 ml) was added to filter insoluble salts. The filtrate was purified in Sephadex LH-20 (100 ml, 80% hydrated methanol) to give sodium salt of compound (1A) (85 mg, yield: 46.1%). Example 2: 4-[(2R)-(2-acetylamino-2-methoxycarbonyl) ethylthio] methyl-3-oxo -1-cyclopentanecarboxylic acid [Compound 2A] Acetone (6 ml), N-acetyl-L-cysteine methyl ester (110.6 mg, 0.624 mmol), water (2 ml) and 1N sodium hydroxide (1.25 ml) were added to compound (a) (200 mg, 0.624 mmol). The mixture was stirred at room temperature for 2 hours. 1N hydrochloric acid was added to the reaction mixture to adjust the pH to 6.8, and then the mixture was concentrated. The residue was purified in QAE-Sephadex (200 ml, Cl type, 0.05 M-0.3 M aqueous sodium chloride solution, 700 ml each, gradient elution) to afford the desired fractions. After concentrating this fraction, methanol (3 ml) was added to remove insoluble salts by filtration, and the filtrate was purified by Sephadex LH-20 (100 ml, 80% hydrous methanol) to give sodium salt of compound (2A) (140 mg, yield: 66.6%). Example 3: Preparation of (2RS, 4S) -2-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-4-hydroxy-1-cyclopentanone (Compound 3A) (1) (4R) -2-[(2R)-(2-acetylamino-2-methoxycarbonyl) ethylthio] methyl-4 Preparation of -tert-Butyldimethylsiloxy-2-cyclopenten-l-one (Compound 3A-b) (4R) -2- (N, N-dimethylamino) methyl-4-tert-butyldimethylsiloxy-2-cyclopenten-l-one (Compound 3A-a) (370 mg, 1.24 mmol) was dissolved in methanol (4 ml), and iodomethane (0.16 ml, 2.48 mmol) was added to the solution, followed by stirring at room temperature for 2 hours. The reaction solution was concentrated and the residue was added with methanol (3 ml) and N-acetyl-. L-cysteine methyl ester (220 mg, 1.24 mmol) was added. The mixture was stirred at room temperature for 1.5 hours. The reaction solution was concentrated and the residue was purified by silica gel column chromatography (60 ml, dichloromethane: methanol = 40: 1) to give compound (3A-b) (378 mg, yield: 75.7%). (2) (4R) -2-[(2R)-(2-acetylamino-2-methoxycarbonyl) ethylthio] methyl-4 Preparation of Hydroxy-2-cyclopenten-l-one (Compound 3A-c) Methanol (4 ml), water (0.2 ml) and Dowex 50 (H + type, 300 mg) were added to compound (3A-b) (64 mg, 0.16 mmol) and the mixture was stirred at rt for 20 h. The reaction mixture was concentrated and the residue was purified by silica gel column chromatography (20 ml, dichloromethane: methanol = 20: 1) to give compound (3A-c) (33.6 mg, yield: 73.6%). MS (FAB, POS) m / z: 288 (M + H) + (3) (4R) -2-[(2R)-(2-acetylamino-2-methoxycarbonyl) ethylsulfonyl] methyl-4 Preparation of Hydroxy-2-cyclopenten-l-one (Compound 3A-d) Compound (3A-c) (33.6 mg, 0.117 mmol) was dissolved in dichloromethane (3 ml) and, to this solution, m-chloroperbenzoic acid (purity 80%, 50 mg, 0.23 mmol) was added under ice cooling. After stirring for 2 hours at room temperature, water (5 ml) and dichloromethane (5 ml) were added to the reaction mixture, and a saturated sodium hydrogencarbonate solution was added to the mixture until the aqueous solution became neutral. To this mixture was added sodium hydrogen sulfite (20%, aqueous solution. 5 drops), the dichloromethane layer was concentrated, and the residue was purified by silica gel column chromatography (20 ml, dichloromethane: methanol = 10: 1) Compound (3A-d) was obtained (36 mg, yield: 96.4%). MS (FAB, POS) m / z: 320 (M + H) + (4) (4S) -2-[(2R)-(2-acetylamino-2-methoxycarbonyl) ethylsulfonyl] methyl-4 Preparation of Hydroxycyclopentan-1-one (Compound c) To compound (3A-d) (36 mg, 112 mmol) was added ethanol (3 ml), methanol (1.5 ml) and 10% Pd-C (50% wet, 8.8 mg) and the mixture was stirred at room temperature in a hydrogen atmosphere. Stir for 10 hours. The reaction solution was filtered and the filtrate was concentrated to give compound (c) (36 mg, yield: 100%). MS (FAB, POS) m / z: 322 (M + H) + (5) (2RS, 4R) -2-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-4- Preparation of Hydroxy-1-cyclopentanone (Compound 3A) Acetone (3 ml), N-acetyl-L-cysteine (24.3 mg, 0.149 mmol), methanol (1.5 ml) and 1N sodium hydroxide (0.22 ml) were added to compound (c) (48 mg, 0.149 mmol) (500 mg). Was added, and the mixture was stirred at room temperature for 1.5 hours. Silica gel (500 mg) was added to the reaction solution, and the mixture was concentrated to dryness. The residue was purified by silica gel column chromatography (80 ml, dichloromethane: methanol: acetic acid = 5: 1: 0.1) and then concentrated again. The residue was dissolved in water (4 ml), adjusted to pH 6.8 with 1N sodium hydroxide and the solution was concentrated to give the sodium salt of compound (3A) (26.6 mg, yield: 60%). Example 4: (2RS, 4S) -2-[(2R) -3-acetylamino-3- [1-{(2S) -methoxycarbonyl} pyrrolidinyl] -3-oxypropylthio] methyl- Preparation of 4-hydroxy-1-cyclopentanone (Compound 4A) Compound (3) (28.2 mg, 0.1 mmol) and proline methyl ester hydrochloride (16.95 mg) were dissolved in dimethylformamide (3 ml), and in this solution triethylamine (14.1 μl), 1-hydroxy under ice-cooling -Benzotriazole (16.5 mg, 0.12 mmol) and dicyclohexylcarbodiimide (23.1 mg) were added. The mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated and the residue was purified by silica gel column chromatography (30 ml, dichloromethane: methanol = 10: 1) to give compound (4A) (18.2 mg, yield: 47%). Example 5: 2-((2R) -2-acetylamino-2-methoxycarbonyl} ethylthio) methyl-3-oxo Preparation of -1-Indancarboxylic Acid (Compound 6A) To a mixture of 3-oxo-1-indanecarboxylic acid (191 mg, 1.08 mmol) and piperidine (92.3 mg, 1.08 mmol) was added 37% formalin (0.088 ml, 1.08 mmol), which was then mixed at room temperature. Stir for 3 hours. The reaction solution was concentrated, ethanol (3 ml) and N-acetyl-L-cysteine methyl ester (80 mg, 0.45 mmol) were added to the residue, and the mixture was heated to reflux for 10 minutes, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (100 ml, chloroform: methanol: acetic acid = 30: 1: 0.5) to give compound (6A) (62 mg, yield: 15.7%). Example 6: (1R, 2S) -2-[(2R)-{2-acetylamino-3-oxo-3- (1-pyrrolidinyl)} propylthio] methyl-3-oxo-1-cyclopentane Preparation of Carboxylic Acid (Compound 1B) (1) Preparation of (2S, 3R) -3-acetoxymethyl-2-[(2RS) -2,3-bis (hydroxy) propylthio] methylcyclopentanone (Compound A-2) (2R, 3R) -2,3-bis (acetoxymethyl) cyclopentanone (Compound A) (20.56 g, 90.17 mmol) was added to acetone (178 ml) to alpha-thioglycerine (9.558 g, 90.17). mmol) was added. Methanol (20 ml) and 1N sodium hydroxide (90.17 ml) were then added to the mixture and stirred for 40 minutes at room temperature. 1N hydrochloric acid was added to the reaction solution to adjust pH to 7.0, and the mixture was concentrated. The obtained residue was dissolved in methanol (200 ml) and silica gel (120 g) was added to this solution. The mixture was concentrated to dryness and then purified by silica gel column chromatography (330 ml, dichloromethane: methanol = 25: 1-5: 1) to give compound (A-2) (22.06 g, yield: 88.63%). . (2) Preparation of (2S, 3R) -3-acetoxymethyl-2-[(2RS)-(2,3-O-isopropylidene) propylthio] methylcyclopentanone (Compound A-3) Compound (A-2) (22.06 g, 79.92 mmol) was dissolved in anhydrous acetone (120 ml), and in this solution, p-toluenesulfonic acid monohydrate (1.5 g) and dimethoxypropane (29.46 ml, 240 mmol) under ice-cooling. ) Was added. The mixture was stirred for 30 minutes at room temperature. Water (150 ml) and ethyl acetate (300 ml) were added to the reaction mixture, and the pH of the aqueous phase was adjusted to 7.0 with saturated sodium bicarbonate. The aqueous phase was extracted twice with ethyl acetate (300 ml), then the ethyl acetate phase was washed with saturated aqueous sodium chloride solution (160 ml), then dried over sodium sulfate and concentrated under reduced pressure to give compound (A-3) ( 24.00 g, yield: 95.0%). (3) Preparation of (2S, 3R) -3-hydroxymethyl-2-[(2RS)-(2,3-O-isopropylidene) propylthio] methylcyclopentanone (Compound A-4) Compound (A-3) (25.22 g, 79.81 mmol) was dissolved in methanol (253 ml) and 1N sodium hydroxide (50 ml) was added to this solution under ice cooling. The mixture was stirred for 18 minutes at room temperature. 1N hydrochloric acid was added to the mixture while cooling with ice to adjust the pH to 5.8, and then concentrated to dryness under reduced pressure to obtain a residue. Water (50 ml) was added to this residue and extracted three times with ethyl acetate (200 ml). The ethyl acetate layer was washed with saturated aqueous sodium chloride solution (100 m), dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (300 ml, dichloromethane: methanol = 30: 1) to give compound (A-4) (18.67 g, yield: 85.3%). (4) Preparation of (2S, 3R) -3-hydroxymethyl-2-[(2RS)-(2,3-O-isopropylidene) propylsulfonyl] methylcyclopentanone (Compound A-5) Compound (A-4) (5.558 g, 20.28 mmol) was dissolved in dichloromethane (55 ml) and, in this solution, dichloromethane (m. Chloroperbenzoic acid (purity 80%, 8.74 g, 40.56 mmol) under ice-cooling ( 85 ml) was added to the solution. The mixture was stirred at room temperature for 1 hour. The reaction solution was filtered and 20% sodium hydrogen sulfite (6.48 ml), saturated aqueous sodium carbonate solution (16.2 ml) and water (50 ml) were added to the filtrate, followed by stirring for 10 minutes. After liquid-liquid separation, the dichloromethane layer was washed with saturated aqueous sodium chloride solution (100 ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (150 ml, hexane: ethyl acetate = 1: 3) to give compound (A-5) (5.798 g, yield: 93.4%). (5) Preparation of (1R, 2S) -2-[(2RS)-(2,3-O-isopropylidene) propylsulfonyl] methyl-3-oxo-1-cyclopentanecarboxylic acid (Compound C) Compound (A-5) (5.80 g, 18.94 mmol) was dissolved in acetone (320 ml) and Jones reagent was added to this solution while stirring to keep the reaction solution orange. 2-propanol was added to this reaction mixture under ice-cooling until the reaction liquid turned green. The mixture was concentrated under reduced pressure to remove acetone, water (120 ml) was added to the residue, and the mixture was extracted twice with dichloromethane (200 ml). The dichloromethane layer was washed with saturated aqueous sodium chloride solution (80 ml), dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain Compound (C) (4.59 g, yield: 75.7%). (6) (1R, 2S) -2-[(2R)-{2-acetylamino-3-oxo-3- (1-pyrrolidinyl)} propylthio] methyl-3-oxo-1-cyclopentanecar Preparation of Acids (Compound 1B) Compound (C) (32 mg, 0.1 mmol) is dissolved in acetone (2 ml), to which (2R) -2-acetylamino-3-oxo-3- (1-pyrrolidinyl)} propanethiol (21.6 mg, 0.1 mmol) of acetone (1 ml) solution was added. The mixture was stirred at room temperature for 2 hours, 1N hydrochloric acid was added to the reaction solution to adjust the pH to 6.8, and the mixture was concentrated. The residue was purified by QAE-Sephadex (Cl type, 110 ml, 0.05-0.5 M NaCl, 300 ml each, gradient elution) to obtain the desired fractions. After adjusting the pH to 2.6, the product was adsorbed on DIAION-SP207 (10 ml, Nippon Rensui Corporation), washed with water and eluted with 80% hydrous methanol. After adjusting to pH 6.8 with 1N sodium hydroxide, the eluate was concentrated to dryness to obtain sodium salt of compound (1B) (26 mg, yield: 68.7%). Example 7: (1R, 2S) -2-[(2R)-{2-acetylamino-3- (4-morpholinyl) -3-oxo} propylthio] methyl-3-oxo-1-cyclopentane Preparation of Carboxylic Acid (Compound 2B) Compound (C) (32 mg, 0.1 mmol) was dissolved in acetone (2 ml), and (2R) -2-acetylamino-3- (4-morpholinyl) -3-oxopropanethiol (23.2 mg , 0.1 mmol) of acetone (1 ml) was added. The mixture was stirred at room temperature for 1.5 hours. Purification was carried out in the same manner as in Example 1, to obtain a sodium salt of compound (2B) (22.4 mg, yield: 56.8%). Example 8: (1R, 2S) -2-[(2R)-{2-acetylamino-3-oxo-3- (1-piperidinyl) propylthio}] methyl-3-oxo-1-cyclopentane Preparation of Carboxylic Acid (Compound 3B) Compound (C) (32 mg, 0.1 mmol) is dissolved in acetone (2 ml), and (2R) -2-acetylamino-3- (1-piperidinyl) -3-oxopropanethiol (23.2 mg 0.1 mmol) of acetone (1 ml) and 1N sodium hydroxide (0.2 ml) were added. The mixture was stirred at room temperature for 1.5 hours. Purification was carried out in the same manner as in Example 6, to obtain a sodium salt of compound (3B) (26.0 mg, yield: 66.3%). Example 9: (1R, 2S) -2-[(2R)-{2-carboxy-2-pentafluoropropionylamino) ethylthio] methyl-3-oxo-1-cyclopentanecarboxylic acid (Compound 4B Manufacturing Compound (C) (32 mg, 0.1 mmol) is dissolved in acetone (2 ml), to which (2R) -2-carboxy-2-pentafluoropropionylaminoethanethiol (25.3 mg, 0.1 mmol) of acetone (1 ml) solution, methanol (1 ml) and 1N sodium hydroxide (0.3 ml) were added. The mixture was stirred at room temperature for 1.5 hours. Purification was carried out in the same manner as in Example 1 to obtain the sodium salt of compound (4B) (30.0 mg, yield: 66.5%). Example 10: trans-2-[(2R)-{2-acetylamino-3-oxo-3- (1-pyrrolidinyl)} propylthio] methyl-3-methoxycarbonyl-1-cyclopentanone Preparation of (Compound 5B) (1) Preparation of trans-3-acetoxy-2- [2,3-bis (hydroxy) propylthio] methylcyclopentanone (Compound a-2) An acetone (160 ml) solution of trans-2,3-bis (acetoxymethyl) cyclopentanone (Compound (a), 18.72 g, 81.8 mmol) is added to alpha-thiogululinserine (8.7 g) and the mixture is Stir at room temperature for 20 minutes. The reaction solution was concentrated, and the obtained residue was dissolved in methanol, and silica gel (100 g) was added thereto, followed by concentration. The residue was purified by silica gel column chromatography (300 ml, dichloromethane: methanol = 20: 1-5: 1) to give compound (a-2) (21.88 g, yield: 96.8%). (2) Preparation of trans-3-acetoxy-2- [2,3-O-isopropylidene) propylthio] methylcyclopentanone (Compound a-3) Compound (a-2) (21.9 g, 79.27 mmol) was dissolved in anhydrous acetone (120 ml), and p-toluenesulfonic acid monohydrate (1.4 g) and dimethoxypropane (29.4 ml) were added to this solution under ice cooling. It was. The mixture was stirred for 30 minutes at room temperature. Water (140 ml) and ethyl acetate (280 ml) were added to the reaction mixture, and then the pH of the aqueous phase was adjusted to 7.0 with saturated sodium bicarbonate solution. The aqueous phase was extracted twice with ethyl acetate (280 ml), the ethyl acetate layer was washed with saturated aqueous sodium chloride solution (150 ml), dried over anhydrous sodium sulfate and concentrated to give compound (a-3) (23.34 g , Yield: 93.2%). (3) Preparation of trans-3-hydroxymethyl-2- [2,3-O-isopropylidene) propylthio] methylcyclopentanone (Compound a-4) Compound (a-3) (1097 mg, 3.47 mmol) was dissolved in methanol (200 ml) and 1N sodium hydroxide (3.47 ml) was added to this solution under ice cooling. The mixture was stirred at room temperature for 15 minutes. 1N hydrochloric acid was added to the reaction mixture under ice-cooling to adjust the pH to 7.0, and the mixture was concentrated. Water (3 ml) was added to the obtained residue, followed by extraction three times with ethyl acetate (15 ml), the ethyl acetate layer was washed with saturated aqueous sodium chloride solution (10 ml), dried over anhydrous sodium sulfate and concentrated. . The obtained residue was purified by silica gel column chromatography (50 ml, chloroform: methanol = 30: 1) to obtain compound (a-4) (739 mg, yield: 77.5%). (4) Preparation of trans-3-hydroxymethyl-2- [2,3-O-isopropylidene) propylsulfonyl] methylcyclopentanone (Compound a-5) Compound (a-4) (5140 mg, 18.76 mmol) was dissolved in dichloromethane (50 ml) and, in this solution, dichloromethane (m. Chloroperbenzoic acid (purity 80%, 80.93 mg, 37.32 mmol) under ice-cooling ( 80 ml) was added to the solution. The mixture was stirred at room temperature for 2 hours. The reaction solution was filtered, and 20% sodium hydrogen sulfite (6 ml), saturated aqueous sodium carbonate solution (6 ml) and water (50 ml) were added to the filtrate, followed by stirring. After liquid-liquid separation, the dichloromethane layer was washed with saturated aqueous sodium chloride solution (30 ml), dried over anhydrous sodium sulfate and concentrated. The obtained residue was purified by silica gel column chromatography (160 ml, hexane: ethyl acetate = 1: 3) to give compound (a-5) (4610 mg, yield: 80.3%). (5) Preparation of trans-2-[(2,3-O-isopropylidene) propylsulfonyl] methyl-3-oxo-1-cyclopentanecarboxylic acid (compound c) Compound (a-5) (2630 mg, 8.59 mmol) was dissolved in acetone (150 ml) and Jones reagent was added to this solution while stirring to bring the reaction solution to orange color. 2-propanol was added to this reaction mixture under ice-cooling until the reaction liquid turned green. The mixture was concentrated and water (60 ml) was added to the residue, then the mixture was extracted three times with dichloromethane (100 ml). The dichloromethane layer was washed with saturated aqueous sodium chloride solution (40 ml), dried over anhydrous sodium sulfate and concentrated to give compound (c) (1948 mg, yield: 70.8%). (6) trans-2-[(2R)-{2-acetylamino-3-oxo-3- (1-pyrrolidinyl)} propylthio] methyl-3-methoxycarbonyl-1-cyclopentanone ( Preparation of Compound 5B) Compound (c) (32 mg, 0.1 mmol), (2R) -2-acetylamino-3-oxo-3- (1-pyrrolidinyl)} propanethiol (21.6 mg, 0.1 mmol) and 1N sodium hydroxide (0.2 ml) was reacted and then purified in the same manner as in Example 1 to obtain sodium trans-2-[(2R)-{2-acetylamino-3-oxo-3- (1-pyrrolidinyl)} ethylthio] Methyl-3-oxo-1-cyclopentanecarboxylate was obtained. This product was dissolved in DMF (3 ml), to which methyl iodide (20 μl) was added and then stirred at room temperature for 35 minutes. The reaction solution was concentrated to dryness and the residue was purified by silica gel column chromatography (20 ml, dichloromethane: methanol = 25: 1) to give compound (5B) (18 mg, yield: 48.6%). Example 11: trans-2-[(2R)-[2-acetylamino-3- {1- (2S) -2-methoxycarbonylpyrrolidinyl)}-3-oxo] propylthio] methyl-3 Preparation of -oxo-1-cyclopentanecarboxylic acid (compound 6B) Compound (c) (53 mg, 0.165 mmol) and (2R) -2-acetylamino-3- [1-{(2S) -2-methoxycarbonyl] pyrrolidinyl} -3-oxopropanethiol (45.3 mg, 0.165 mmol) was dissolved in acetone (3 ml), and methanol (1 ml) and 1N sodium hydroxide (0.33 ml) were added to the solution, followed by stirring at room temperature for 1.5 hours. 1N hydrochloric acid was added to the reaction mixture to adjust the pH to 2.5, and the mixture was concentrated to dryness. The residue was purified by silica gel column chromatography (25 ml, dichloromethane: methanol = 10: 1) to give compound (6B) (40.3 mg, yield: 58.9%). Example 12: trans-2-[(2R)-[2-acetylamino-3- {1- (2S) -2-methoxycarbonylazetidinyl)}-3-oxo] propylthio] methyl-3 -Oxo-1-cyclopentanecarboxylic acid (compound 7B) Compound (c) (92 mg, 0.288 mmol) and (2R) -2-acetylamino-3- [1-{(2S) -2-methoxycarbonyl] azetidinyl} -3-oxopropanethiol (75.0 mg, 0.288 mmol) was dissolved in acetone (3 ml), and methanol (1 ml) and 1N sodium hydroxide (0.58 ml) were added to the solution, followed by stirring at room temperature for 1.5 hours. 1N hydrochloric acid was added to the reaction mixture to adjust the pH to 2.5, and the mixture was concentrated to dryness. The residue was purified by silica gel column chromatography (25 ml, dichloromethane: methanol = 10: 1) to give compound (7B) (43.0 mg, yield: 373 mg). Example 13: Preparation of trans-2-[(2R)-(2-carboxy-2-pentafluoropropionylamino) ethylthio] methyl-3-hydroxymethyl-1-cyclopentanone (Compound 8B) Compound (c) (45.6 mg, 0.2 mmol) was dissolved in acetone (4 ml), and (2R) -2-carboxy-2-pentafluoropropionylaminoethanethiol (50.6 mg, 0.2 mmol) in methanol (1.5 ml) solution and 1N sodium hydroxide (0.8 ml) were added. The mixture was stirred at room temperature for 1 hour. 1N sodium hydroxide was added to the solution to adjust the pH to 2.5, and the mixture was concentrated to dryness. The residue was purified in the same manner as in Example 1 to obtain compound (8B) (71 mg, yield: 83.1%). Example 14 Preparation of trans-2-[(11-acetylamino-11-carboxy) undecylthio] methyl-3-oxo-1-cyclopentanecarboxylic acid (Compound 9B) (1) Preparation of 1-acetylamino-11-benzyloxy-1,1-diethoxycarbonyl undecane (Compound r-2) Anhydrous ethanol (10.5 ml) and diethylacetamide malonate (2661 mg, 12.25 mmol) were added to sodium ethoxide (834 mg, 12.25 mmol) and stirred for 10 minutes, then to this mixture 1-benzyloxy-10-iodine Dodecane (Compound q-1) (2661 mg, 12.25 mmol) was added. The mixture was heated to reflux for 4 hours and concentrated under reduced pressure. Chloroform (200 ml) and water (100 ml) were added to the residue. The organic layer was washed with saturated aqueous sodium chloride solution (100 ml), dried over anhydrous sodium sulfate and then concentrated. The residue was purified by silica gel column chromatography (300 ml, hexane: ethyl acetate = 4: 1) to give compound (r-2) (5080 mg, yield: 89.7%). (2) Preparation of 1-acetylamino-1,1-diethoxycarbonyl-11-hydroxyundecane (Compound r-3) (Compound r-2) (5090 mg, 10.99 mmol) was dissolved in ethanol (132 ml), and 10% Pd-C (50% wet, 1100 mg) was added thereto. The mixture was stirred at room temperature under hydrogen atmosphere for 3 hours. The reaction solution was filtered, and the filtrate was concentrated to give compound (r-3) (3760 mg, yield: 91.7%). MS (FAB, POS) m / z: 374 (M + H) + (3) Preparation of 1-acetylamino-1-carboxy-11-hydroxyundecane (Compound r-4) (Compound r-3) (3760 mg, 10.08 mmol) was dissolved in ethanol (6 ml), adjusted to pH 2.0 with 1N hydrochloric acid, and the mixture was heated to reflux for 8 hours. 1N hydrochloric acid was added to maintain the pH at 2.0 during the heating reflux. The reaction solution was cooled to precipitate colorless crystals. This crystal was filtered to give compound (r-4) (1341 mg, yield: 48.7%). MS (FAB, POS) m / z: 274 (M + H) < + > (4) Preparation of 1-acetylamino-11-acetylthio-1-methoxycarbonyl undecane (Compound r-5) (Compound r-4) (176 mg, 0.64 mmol) was dissolved in methanol (2 ml), and TMS-diazomethane was added thereto. After reacting for 15 minutes, the mixture was concentrated. The residue was added to a solution of benzene: acetone (1: 1, 3 ml) of 2-fluoro-1-methylpyridinium p-toluenesulfonate (190 mg, 0.637 mmol), to which triethylamine (88.6 Μl) was added. The mixture was stirred at 30 ° C. for 2 hours, and then thioacetic acid (44.5 μl) and triethylamine (88.6 μl) were added to the reaction solution. The mixture was heated to reflux for 2 hours, and the reaction solution was concentrated, and then dichloromethane (10 ml) and water (5 ml) were added to the residue to separate the liquid. The aqueous layer was extracted twice with dichloromethane (10 ml), the dichloromethane layer was taken, dried over anhydrous sodium sulfate and concentrated. The obtained residue was purified by silica gel column chromatography (25 ml, dichloromethane) to give compound (r-5) (222 mg, yield: 100%). (5) Preparation of 1-acetylamino-1-carboxy-11-mercaptodecane (Compound r) Compound (r-5) (222 mg, 0.64 mmol) was dissolved in methanol (3 ml), 1N hydrochloric acid (1.3 ml) was added thereto, and the mixture was stirred at room temperature for 2 hours. 1N hydrochloric acid was added to the solution to adjust the pH to 3.0, and the mixture was concentrated. The obtained residue was purified by silica gel column chromatography (20 ml, dichloromethane: methanol = 15: 1) to give compound (r) (123 mg, yield: 66.9%). MS (ESI, NEG) m / z: 288 (M−H) − (6) Preparation of trans-2-[(11-acetylamino-11-carboxy) undecylthio] methyl-3-oxo-1-cyclopentanecarboxylic acid (Compound 9B) Compound (r) (57.8 mg, 0.2 mmol) and trans-2-[(2RS)-(2,3-O-isopropylidene) propylsulfonyl] methyl-3-oxo-1-cyclopentanecarboxylic acid ( Compound c) (64 mg, 0.2 mmol) was dissolved in acetone (3 ml), 1N sodium hydroxide (0.6 ml) was added thereto, and the mixture was stirred at room temperature for 1.5 hours. 1N hydrochloric acid was added to the solution to adjust the pH to 6.8, and then the mixture was concentrated, and the obtained residue was purified by QAE-Sephadex. The pH was adjusted back to 6.8 and the product was adsorbed onto activated carbon (12 ml), then washed with water and eluted with 80% hydrous methanol. The eluate was concentrated to give compound (9B) (28.9 mg, yield: 32.7%). Example 15: (1R, 2S) -2-[(2R) -2-acetylamino-3-oxo-3- {1- (4-phenyl) piperazinyl} propylthio] methyl-3-oxo-1 Preparation of Cyclopentanecarboxylic Acid (Compound 13B) (2R) -2-acetylamino-3-oxo-3- [1- (4-phenylpiperazinyl)] propanethiol (29.3 mg, 1 mmol), acetone (1 ml) and 1N sodium hydroxide (0.2 ml) Was added to compound (C) (32 mg, 1 mmol) and the mixture was stirred at room temperature for 3 hours. 1N hydrochloric acid was added to the reaction solution to adjust the pH to 2.8, and silica gel (200 mg) was added thereto, and the mixture was concentrated to dryness. The residue was purified by silica gel column chromatography (30 ml, chloroform: methanol = 10: 1) to give compound (13B) (28.5 mg, yield: 63.7%). Example 16: Preparation of (1R, 2S) -2- {3- (3-pyridyl) propylthio} methyl-3-oxo-1-cyclopentanecarboxylic acid (Compound 14B) Compound (C) (32 mg, 0.1 mmol) was dissolved in acetone (1 ml), to which methanol solution of 3- (3-pyridyl) propanethiol (15.3 mg, 0.1 mmol) (1 ml) and 1N hydroxide were added. Sodium (0.18 ml) was added. After the mixture was stirred at room temperature for 3 hours, the mixture was concentrated and the residue was purified by QAE-Sephadex (Cl type, 110 ml, 0.05 M to 0.5 M aqueous sodium chloride solution, 300 ml each, gradient elution). After the desired fractions were collected and adjusted to pH 2.8, the product was adsorbed on SEPHABEADS SP207 (12 ml, Nippon Rensui Corporation), washed with water and eluted with 80% hydrous methanol. Compound (14B) was obtained by extracting the desired fractions (29.6 mg, yield: 89.8%). Example 17: (1R, 2S) -2- [3- {3- (1-methylpyridinium iodide)} propylthio] methyl-3-oxo-1-cyclopentanecarboxylic acid (Compound 15B) Produce Compound (C) (32 mg, 0.1 mmol) was dissolved in acetone (1 ml), and 3- {3- (1-methylpyridinium iodide)} propanethiol (30 mg, 0.1 mmol) in methanol Solution (1.5 ml) and 1N sodium hydroxide were added. The mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated and the residue was purified in the same manner as in Example 16 to obtain Compound (15B) (17.8 mg, yield: 41%). Example 18 Preparation of 5-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-2-cyclopenten-l-one (Compound 1C) (1) (4R) -2-[(2R)-(2-acetylamino-2-methoxycarbonyl) ethylthio] methyl-4-tert-butyldimethylsiloxy-2-cyclopenten-l-one ( Preparation of Compound a) Compound (c) (370 mg, 1.24 mmol) was dissolved in methanol (4 ml) and methyl iodide (0.16 ml, 2.48 mmol) was added to this solution. The mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated and methanol (3 ml) and N-acetyl-L-cysteine methyl ester (220 mg, 1.24 mmol) were added to the residue. The mixture was stirred at room temperature for 1.5 hours, and the reaction solution was concentrated, and then the residue was purified by silica gel column chromatography (60 ml, dichloromethane: methanol = 40: 1) to obtain compound (a-1) ( 378 mg, yield: 75.7%). (2) (4R) -2-[(2R)-(2-acetylamino-2-methoxycarbonyl) ethylsulfonyl] methyl-4-tert-butyldimethylsiloxy-2-cyclopenten-1-one Preparation of (Compound a) Compound (a-1) (378 mg, 0.94 mmol) was dissolved in dichloromethane (30 ml) and to this solution, m-chloroperbenzoic acid (406 mg, purity 80%, 1.88 ml) was added under ice cooling. Water (15 ml) and 20% sodium hydrogen arsenite (3 ml) were added to the reaction solution, followed by addition of saturated sodium bicarbonate solution until the pH of the aqueous phase reached 7.0. The dichloromethane layer was washed with saturated aqueous sodium chloride solution and concentrated. The residue was purified by silica gel column chromatography (50 ml, dichloromethane: methanol = 10: 1) to give compound (a-2) (355 mg, yield: 87.3%). (3) (4R) -2-[(2R)-(2-acetylamino-2-methoxycarbonyl) ethylsulfonyl] methyl-4-tert-butyldimethylsiloxy-2-cyclopentan-1-one Preparation of (Compound a) Compound (a-2) (355 mg, 0.82 mmol) was dissolved in ethanol (20 ml) and 10% Pd-C (80 mg, 50% hydration) was added to this solution. The mixture was stirred at room temperature under hydrogen atmosphere for 5 hours. The reaction solution was filtered, and the filtrate was concentrated to give compound (a) (330 mg, yield: 92.9%). MS (FAB, POS) m / z: 436 (M + H) + (4) (4R) -2-[(2R)-(2-acetylamino-2-carbonyl) ethylthio] methyl-4-tert-butyldimethylsiloxy-2-cyclopentan-1-one (Compound a -3) Preparation Acetone (2 ml), methanol (8 ml), N-acetyl-L-cysteine methyl ester (123.9 mg, 0.76 mmol) and 1N sodium hydroxide (1.52 m) were added to compound (a) (330 mg, 0.76 mmol) The mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated and purified using Sephadex LH-20 (200 ml, 80% hydrous methanol) to give compound (a-3) (299 mg). This compound was used in the next reaction without purification. (5) Preparation of 5-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-2-cyclopenten-l-one (Compound 1C) Methanol (15 ml), water (1 ml) and Dowex 50 (H + type, 300 mg) were added to compound (a-3) (299 mg, 0.76 mmol) and the mixture was stirred at rt for 20 h. After filtration, silica gel (1 g) was added to the filtrate, and then concentrated. The obtained residue was purified by silica gel column chromatography (80 ml, dichloromethane: methanol: acetic acid = 5: 1: 0.1) to give compound (1C) (83 mg, yield: 39%). Example 19 Preparation of (4R) -2-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-4-hydroxy-2-cyclopenten-l-one (Compound 2C) Acetone (2 ml), methanol (4 ml), N-acetyl-L-cysteine (61.9 mg, 0.39 mmol) and 1N sodium hydroxide (0.76 m) were added to (4R) -2-[(2R)-(2-acetyl To amino-2-methoxycarbonyl) ethylsulfonyl] methyl-4-tert-butyldimethylsiloxy-2-cyclopenten-l-one (165 mg, 0.38 mmol), and the mixture was stirred at room temperature for 2 hours. It was. After concentrating the reaction solution, methanol (5 ml), water (1 ml) and Dowex 50 (H type, 700 mg) were added to the residue, followed by stirring at room temperature for 16 hours. After filtration, silica gel (500 mg) was added to the reaction mixture, which was then concentrated. The residue was purified by silica gel column chromatography (80 ml, dichloromethane: methanol: acetic acid = 5: 1: 0.1). After concentration the residue was dissolved in water (10 ml) and adjusted to pH 6.9 by addition of 1N sodium hydroxide. Thus, sodium salt of compound (2C) (61 mg, yield: 54.4%) was obtained. Example 20 Preparation of 2-[(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-3-hydroxy-2-cyclopenten-l-one (Compound 3C) N-acetyl-L-cysteine (193 mg, 1.18 mmol), methanol (2 ml) and acetone (4 ml) and 1N sodium hydroxide (2.36 ml) were added to compound (d) (347 mg, 1.18 mmol), The mixture was stirred at room temperature. 1N sodium hydroxide was added to this mixture until the reaction solution became neutral (4 hours). Silica gel (1.2 g) was added to the reaction solution, and then concentrated. The residue was purified by silica gel column chromatography (100 ml, dichloromethane: methanol: acetic acid = 5: 1: 0.1 to 2.5: 1: 0.1) to give compound (3C) (308 mg, yield: 95.6%). Example 21 Preparation of 3-{(2R) -2-acetylamino-2-carboxyethylthio} methyl-4-oxo-1-n-pentanoic acid (Compound 1D) Compound (a) (256.3 mg, 2.00 mmol) was dissolved in tetrahydrofuran (3 ml) and in this solution 1,8-diazabicyclo [5.4.0] -undeca-7-ene (609 mg, 4.0 mmol) was added. The mixture was stirred overnight at room temperature. Amberlist-15 (3 g) was added to the reaction mixture and stirred for 5 minutes. The resin was then filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (40 ml, hexane: ethyl acetate = 3: 2-1: 1) to fractionate fractions containing compound (b). This fraction was concentrated under reduced pressure. The obtained residue was dissolved in tetrahydrofuran (3 ml). N-acetyl-L-cysteine (107.7 mg, 0.66 mmol) and triethylamine (265.1 mg, 2.62 mmol) were added to the solution, the mixture was stirred overnight at room temperature, and the reaction solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (40 ml, methylene chloride: methanol = 10: 1 to 2: 1). The desired fractions were concentrated under reduced pressure and dissolved in tetrahydrofuran (3 ml) and methanol (1 ml). Amberlist-15 (2 g) was added to the solution, the mixture was stirred for 3 minutes, the resin was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (40 ml, methylene chloride: methanol = 10: 1) to give compound (1D) (40.9 mg, yield: 7%). 3-{(2R) -2-acetylamino-2-methoxycarbonylethylthio} methyl-4-oxo-1-n-pentanoic acid (Compound 2D) can be prepared in the same manner as described above. Example 22 Preparation of trans-2-{(2R) -2-acetylamino-2-methoxycarbonylethylthio} methyl-3-ethoxycarbonyl-1-cyclobutanone (Compound 3D) (1) Preparation of trans-2-hydroxymethyl-3-ethoxycarbonyl-1-cyclobutanone (Compound e-2) To the solution obtained by adding n-butyl lithium (1.59 M / hexane solution, 2.79 mmol) to tetrahydrofuran (8 ml) was added diisopropylamine (0.296 g, 2.92 mmol) under ice-cooling and the mixture was stirred for 10 minutes. After cooling to −78 ° C., to this mixture was added dropwise a solution of tetrahydrofuran (3 ml) of 3-ethoxycarbonyl-1-cyclobutanone (Compound e-1) (355.4 mg, 2.50 mmol). Then, stirred for 15 minutes. After raising the temperature to 0 ° C., the mixture was stirred for 15 minutes and cooled to −78 ° C. again. Hexamethylphosphoramide (535.8 mg, 2.99 mmol) was added thereto, stirred for 5 minutes, and then a solution obtained by cracking formaldehyde at 160 ° C. and trapping in diethyl ether at −78 ° C. was added via a needle. Hydrochloric acid was added to terminate the reaction, and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (50 ml, hexane: diethyl ether = 1: 1-1: 2) to give compound (e-2) (50.7 mg, yield: 12%). (2) Preparation of 2-methylidene-3-ethoxycarbonyl-1-cyclobutanone (Compound f) Compound (e-2) was dissolved in methylene chloride (2 ml), and triethylamine (60.1 mg, 0.59 mmol) and mesyl chloride (36.7 mmg, 0.32 mmol) were added to the solution under ice cooling. The mixture was stirred for 30 minutes under the same conditions, and water and diethyl ether were added thereto and separated. The obtained organic layer was washed with water, washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain compound (f) (40.3 mg, yield: 96%). (3) Preparation of trans-2-{(2R) -2-acetylamino-2-methoxycarbonylethylthio} methyl-3-ethoxycarbonyl-1-cyclobutanone (Compound 3D) Compound (f) (40.3 mg, 0.26 mmol) was dissolved in methylene chloride (2 ml), and in this solution N-acetyl-L-cysteine (46.1 mg, 0.26 mmol) and triethylamine (10.9 mg, 0.11) under ice cooling. mmol) was added, followed by stirring for 1 hour under the same conditions. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (20 ml, methylene chloride: methanol = 40: 1) and Sephadex LH-20 (10 ml, eluted with methanol) to give Compound (3D). Obtained (27.4 mg, yield: 36.4%). Example 23 Preparation of trans-2-{(2R) -2-acetylamino-2-carboxyethylthio} methyl-3-oxo-1-cyclobutanecarboxylic acid (compound 4D) To the compound (3) (17.4 mg, 0.05 mmol) was added 3N aqueous hydrochloric acid solution (4 ml), and the mixture was stirred overnight at room temperature. The reaction solution was concentrated under reduced pressure, and the residue was purified by Sephadex LH-20 (100 ml and 200 ml, eluted with methanol) twice and silica gel column chromatography (2 ml, methylene chloride: methanol = 20: 1 to 2: Purification twice by 1) afforded compound (4D) (6.0 mg, yield: 40%). Example 24 Preparation of trans-3-acetoxymethyl-2- (2,3-dihydroxypropylthio) methyl-1-cyclobutanone (Compound 5D) (1) Preparation of 3-acetoxymethyl-2-methylidene-1-cyclobutanone (Compound d) To compound (c) (30 mg, 0.14 mmol) was added tetrahydrofuran (3 ml) and 1,8-diazabicyclo [5.4.0] -undeca-7-ene (25.5 mg, 0.168 mmol), The mixture was stirred at room temperature for 1 hour. The reaction solution was purified by silica gel column chromatography (10 ml, hexane: ethyl acetate = 2: 1) to obtain compound (d) (23 mg, yield: 95.5%). (2) Preparation of trans-3-acetoxymethyl-2- (2,3-dihydroxypropylthio) methyl-1-cyclobutanone (Compound 5D) Compound (d) (23 mg, 0.133 mmol) was dissolved in acetone (1 ml), and to this solution was added a methanol (1 ml) solution of alpha-thioglycerine (11 μl, 0.133 mmol), and then the mixture was Stirred at room temperature for 1 hour. The reaction solution was concentrated and the residue obtained was purified by silica gel column chromatography (20 ml, dichloromethane: methanol = 20: 1) to give compound (5D) (19 mg, yield: 51.3%). Example 24 Preparation of 2-{(2R) -2-acetylamino-2-carboxyethylthio} methyl-3-oxo-1-cyclohexanecarboxylic acid (Compound 6D) (1) Preparation of 4,5-dimethoxycarbonyl-3-trimethylsiloxy-1-cyclohexene (compound g-3) Compound (g-1) (589 mg, 4.09 mmol) and Compound (g-2) (588 mg, 4.09 mmol) were dissolved in benzene and reacted at 150 ° C for 5 hours. The reaction solution was concentrated, and the residue was purified by silica gel column chromatography (80 ml, hexane: ethyl acetate = 5: 1-3: 1) to give compound (g-3) (875 mg, yield: 74.6%). (2) Preparation of 4,5-bis (hydroxymethyl) -3-hydroxy-1-cyclohexene (Compound g-4) Lithium borohydride is suspended in anhydrous tetrahydrofuran (25 ml), and to this suspension is added dropwise a suspension of anhydrous tetrahydrofuran (4 ml) of compound (g-3) (875 mg, 3.05 mmol) under ice-cooling. It was. After reacting for 2 hours, this mixture was added water (0.196 ml), 15% aqueous sodium hydroxide solution (0.196 ml) and water (0.59 ml). Then stirring was continued. After filtering the suspension, the filtrate was concentrated. The residue was purified by silica gel column chromatography (20 ml, methylene chloride: methanol = 20: 1) to give compound (g-4) (340 mg, yield: 70.5%). (3) Preparation of 5,6-bis (hydroxymethyl) -2-cyclohexen-1-one (Compound g-5) Compound (g-4) (230 mg, 2.02 mmol) was dissolved in acetone (20 ml) and manganese dioxide (1400 mg) was added to this solution. After the reaction, the precipitate was filtered off and the filtrate was concentrated. The residue was purified by silica gel column chromatography (40 ml, methylene chloride: methanol = 10: 1) to give compound (g-5) (205 mg, yield: 61.1%). (4) Preparation of 2,3-bis (acetoxymethyl) -1-cyclohexanone (Compound g-6) Pyridine (10 ml) and acetic anhydride (3 ml) were added to compound (g-5) (205 mg, 1.31 mmol) and the mixture was reacted at room temperature for 2 hours. The reaction solution was concentrated and the residue was subjected to silica gel column chromatography (20 ml, hexane: ethyl acetate = 1: 1). The fractions were concentrated and the concentrate was dissolved in ethanol (20 ml). Palladium-carbon (50% hydration) (50 mg) was added to this solution, and reacted overnight at room temperature under hydrogen atmosphere. The catalyst was filtered off and the filtrate was concentrated. The residue was purified by silica gel column chromatography (30 ml, methylene chloride: methanol = 20: 1) to give compound (g-6) (175 mg, yield: 73.0%). (5) Preparation of 3-acetoxymethyl-2- [2,3- (dihydroxy) propylthio] methyl-1-cyclohexanone (Compound g-7) 2,3-bis (acetoxymethyl) -1-cyclohexanone (Compound g-6) (200 mg, 0.826 mmol) was dissolved in acetone (3 ml) and in this solution alpha-thioglycerine (89.2 mg, A solution of 0.826 mmol) of methanol (1 ml) and a solution of 1N sodium hydroxide (0.826 ml) were added. The mixture was stirred at room temperature for 1 hour. Silica gel (1 g) was added to the reaction mixture, and the residue was purified by silica gel column chromatography (30 ml, dichloromethane: methanol = 20: 1) to give compound (g-7) (175 mg). , Yield: 73.0%). MS (FAB, POS) m / z: 291 (M + H) < + > (6) Preparation of 3-acetoxymethyl-2-[(2,3-O-isopropylidene) propylthio] methyl-1-cyclohexanone (Compound g-8) Compound (g-7) (170 mg, 0.586 mmol) was dissolved in anhydrous acetone (1.5 ml), and in this solution p-toluenesulfonic acid monohydrate (11 mg, 0.06 mmol), dimethoxypropane (0.34 ml, 1.76 mmol) ) Was added and the mixture was stirred at room temperature for 30 minutes. Water (2 ml) was added to the reaction mixture, the mixture was adjusted to pH 7.0 with saturated sodium bicarbonate and the mixture was extracted three times with ethyl acetate (5 ml). The organic layer was washed with saturated aqueous sodium chloride solution (5 ml), dried over anhydrous sodium sulfate and concentrated to give compound (g-8) (191 mg, yield: 98.7%). (7) Preparation of 3-hydroxymethyl-2-[(2,3-O-isopropylidene) propylthio] methyl-1-cyclohexanone (Compound g-9) Compound (g-8) (191 mg, 0.578 mmol) was dissolved in methanol (2 ml), and to this solution water (0.2 ml) and 1N sodium hydroxide (0.57 ml) were added under ice cooling, and the mixture was ice-cooled. Stir for 15 minutes. 1N hydrochloric acid was added to the reaction mixture to adjust the pH to 6.8. Silica gel (500 mg) was added to the reaction mixture, and the residue was purified by silica gel column chromatography (20 ml, dichloromethane: methanol = 30: 1) to obtain a compound (g-9) (155 mg). , Yield: 93.1%). MS (FAB, POS) m / z: 289 (M + H) + (8) Preparation of 3-hydroxymethyl-2-[(2RS)-(2,3-O-isopropylidene) propylsulfonyl] methyl-1-cyclohexanone (Compound g-10) Compound (g-9) (155 mg, 0.538 mmol) was dissolved in dichloromethane (2 ml), and in this solution, dichloromethane solution (5 ml) and m-chloroperbenzoic acid (232 mg, purity 80%, under ice-cooling) 1.07 mmol) was added. The reaction mixture was filtered and water (4 ml) and 20% sodium hydrogen sulfite (0.17 ml) were added to the filtrate. Saturated sodium bicarbonate was added to the mixture until the pH of the aqueous layer reached 7.0. The aqueous layer was extracted twice with dichloromethane (10 ml), then the dichloromethane layer was washed with saturated aqueous sodium chloride solution (15 ml), dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (18 ml, hexane: ethyl acetate = 1: 3) to give compound (g-10) (151 mg, yield: 87.7%). MS (FAB, POS) m / z: 321 (M + H) < + > (9) Preparation of 2-[(2,3-O-isopropylidene) propylsulfonyl] methyl-3-oxo-1-cyclohexanecarboxylic acid (compound g) Compound (g-10) (151 mg, 0.47 mmol) was dissolved in acetone (9 ml), Jones reagent was added to this solution, and the reaction solution was orange. After stirring the mixture for 10 minutes at room temperature, 2-propanol was added to the reaction mixture until the mixture became green. The mixture was concentrated, water (5 ml) was added to the concentrate, and the resulting solution was extracted three times with dichloromethane (5 ml). The dichloromethane layer was washed with saturated aqueous sodium chloride solution (10 ml), dried over anhydrous sodium sulfate and concentrated to give compound (g) (88.6 mg, yield: 56.4%). MS (ESI, NEG) m / z: 333 (M−H) − (10) Preparation of 2-{(2R) -2-acetylamino-2-carboxyethylthio} methyl-3-oxo-1-cyclohexanecarboxylic acid (Compound 6D) Compound (g) (88.6 mg, 0.265 mmol) was dissolved in acetone (3 ml), and in this solution N-acetyl-L-cysteine (43.2 mg, 0.265 mmol), 1N sodium hydroxide (0.78 ml, 0.795 mmol) and Methanol (1 ml) was added. The mixture was stirred at room temperature for 2 hours. 1N hydrochloric acid was added to the mixture to adjust the pH to 6.8, and the residue was purified by Sephadex LH-20 (200 ml, 80% hydrated methanol) to give the compound (6D) (57.7 mg, yield: 60.3%). Example 25 Preparation of 3-{(2R)-(2-acetylamino-2-carboxy) ethylthio] methyl-4-oxo-phenylbutyric acid (Compound 7D) N-acetyl-L-cysteine (39 mg, 0.24 mmol) and ethanol (4 ml) were added to 4-oxo-3- (1-piperidinyl) methyl-4-phenylbutyric acid (66 mg, 0.24 mmol). . The mixture was heated to reflux for 2 hours. After the reaction mixture was concentrated under reduced pressure, water (5 ml) and ethyl acetate (8 ml) were added to the residue. The pH of the aqueous layer was adjusted to 2.0 with 1N hydrochloric acid and then liquid-liquid separation. The mixture was extracted twice with ethyl acetate (8 ml) and the recovered ethyl acetate layer was washed with saturated aqueous sodium chloride solution (5 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20 ml, chloroform: methanol = 20: 1) to give compound (7D) (45 mg, yield: 53.1%). Example 26 Preparation of 3-[(2R)-(2-acetylamino-2-methoxycarbonyl) ethylthio] methyl-4-oxo-phenylbutyric acid (Compound 8D) N-acetyl-L-cysteine methyl ester (66.3 mg, 0.37 mmol) and ethanol (4 ml) in 4-oxo-3- (1-piperidyl) methyl-4-phenylbutyric acid (103 mg, 0.37 mmol) It was added continuously, and this mixture was heated to reflux for 1 hour. The reaction mixture was purified in the same manner as in Example 25 to obtain Compound (8D) (116 mg, yield: 84.5%). Example 27 Preparation of 3-[(2R)-(2-acetylamino-2-methoxycarbonyl) ethylthio] methyl-4- (4-methoxyphenyl) -4-oxobutyric acid (Compound 9D) N-acetyl-L-cysteine methyl ester (66.3 mg, 0.37 mmol) and ethanol (3 ml) were added to 4- (4-methoxyphenyl) -4-oxo-3- (1-piperidyl) methyl-butyric acid ( 109 mg, 0.37 mmol), and the mixture was heated to reflux for 2 hours. Purification was carried out in the same manner as in Example 25, to obtain Compound (9D) (110 mg, yield: 73.4%). Example 28 Preparation of 3- {2- (acetylamino) ethylthio} methyl-4- (4-methoxyphenyl) -4-oxobutyric acid (Compound 10D) N-acetyl-L-cysteamine (45 mg, 0.37 mmol) and ethanol (3 ml) were added to 4- (4-methoxyphenyl) -4-oxo-3- (1-piperidyl) methyl-4- Phenylbutyric acid (109 mg, 0.37 mmol) was added and the mixture was heated to reflux for 2 hours. Purification was carried out in the same manner as in Example 25, to obtain Compound (10D) (93 mg, yield: 72%). Example 29 Preparation of 3- {2- (acetylamino) ethylthio} methyl-4-oxo-4-phenylbutyric acid (Compound 11D) N-acetyl-L-cysteamine (45 mg, 0.37 mmol) and ethanol (3 ml) were added to 4-oxo-4-phenyl-3- (1-piperidyl) methylbutyric acid (103 mg, 0.37 mmol). It was added and the mixture was heated to reflux for 2 hours. Purification was carried out in the same manner as in Example 25, to obtain Compound (11D) (83 mg, yield: 71.7%). Example 30 Preparation of 3- {2- (acetylamino) ethylthio} methyl-4- (4-methylphenyl) -4-oxobutyric acid (Compound 12D) N-acetyl-L-cysteamine (57 mg, 0.47 mmol) and ethanol (3 ml) were added 4- (4-methylphenyl) -4-oxo-3- (1-piperidyl) methylbutyric acid (131 mg, 0.47 mmol) and the mixture was heated to reflux. Purification was carried out in the same manner as in Example 25, to obtain Compound (12D) (114 mg, yield: 73.6%). Example 31 Preparation of 3-{(2R)-(2-acetylamino-2-methoxycarbonyl) ethylthio} methyl-4- (4-methylphenyl) -4-oxobutyric acid (Compound 13D) N-acetyl-L-cysteamine methyl ester (92 mg, 0.52 mmol) and ethanol (3 ml) were added to 4- (4-methylphenyl) -4-oxo-3- (1-piperidyl) methylbutyric acid (142 mg, 0.52 mmol) and the mixture was heated to reflux for 2 hours. Purification was carried out in the same manner as in Example 25, to obtain Compound (13D) (126 mg, yield: 63.5%). Example 32 Preparation of 3-[(2R)-(2-acetylamino-2-methoxycarbonyl) ethylthio] methyl-4-oxo-4- (3-pyridyl) butyric acid (Compound 32D) (1) Preparation of Methyl 4-oxo-4- (3-pyridyl) butyrate (Compound 32D-A) Under nitrogen atmosphere, a solution of 3-pyridinecarboxyaldehyde (10.7 g, 100 mmol) of anhydrous dimethylformamide (20 ml) was added to anhydrous dimethylformamide (80 ml) of sodium cyanide (2.44 g, 50 mmol) at 30 ° C. To the solution was added dropwise over 30 minutes, stirred for 30 minutes and then to the reaction mixture was added dropwise a solution of methyl acrylate (8.6 g, 100 mmol) of anhydrous dimethylformamide (80 ml) over 1 hour, It stirred at 30 degreeC for 3 hours. Acetic acid (0.66 ml) and water (30 ml) were added to the reaction solution, and the mixture was concentrated under reduced pressure after stirring for 10 minutes. Water (360 ml) and chloroform (300 ml x 3) were added to the residue, and the obtained organic phase was washed with saturated aqueous sodium chloride solution (300 ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (650 ml, hexane: ethyl acetate = 1: 1: 1: 2) to give compound (32D-A) (7.87 mg, yield: 40.7%). (2) Preparation of 4-oxo-4- (3-pyridyl) butyric acid (Compound 32D-B) Compound (32D-A) (5.04 g, 26.11 mmol) was dissolved in methanol (60 ml), 1N sodium hydroxide (32 ml) was added to this solution, and the mixture was stirred at room temperature for 3 hours. 2N hydrochloric acid (16 ml) was then added to the reaction mixture, followed by concentration under reduced pressure. The residue was purified by silica gel column chromatography (250 ml, chloroform: methanol: acetic acid = 20: 1: 0.5) to give compound (32D-B) (3.13 mg, yield: 66.9%). (3) Preparation of 4-oxo-4- (3-pyridyl) -3- (1-piperidyl) methylbutyric acid (Compound 32D-C) To compound (32D-B) (246 mg, 1.37 mmol) was added piperidine (140 mg, 1.64 mmol) and 37% formalin (0.133 ml, 1.64 mmol), and the mixture was stirred at 100 ° C. for 2 hours. Silica gel (1.8 g) was added to the reaction solution, concentrated, and the residue was purified by silica gel column chromatography (30 ml, chloroform: methanol: acetic acid = 10: 1: 0.5-10: 5: 3) Compound (32D-C) was obtained (300 mg, yield: 79%). (4) Preparation of 3-[(2R)-(2-acetylamino-2-methoxycarbonyl) ethylthio] methyl-4-oxo-4- (3-pyridyl) butyric acid (Compound 32D) N-acetyl-L-cysteamine methyl ester (96.2 mg, 0.54 mmol) was added to a solution of ethanol (3 ml) of compound (32D-C) (150 ml, 0.54 mmol) and the mixture was heated to reflux for 2 hours. . The reaction mixture was concentrated and the residue was purified by silica gel column chromatography (30 ml, chloroform: methanol: acetic acid = 20: 1: 0.5) to give compound (32D) (89 mg, yield: 44.7%). . Example 33 Preparation of 4-[(2R)-{2-acetylamino-2-carboxy) ethylthio}] methyl-5-oxo-5-phenylpentanoic acid (Compound 38D) (1) Preparation of 4- (1-piperazinyl) methyl-5-oxo-5-phenylpentanoic acid (Compound 38D-A) 4-benzoylbutyric acid (1000.9 mg, 5.21 mmol) was suspended in an aqueous formalin solution (507 mg, 6.25 mmol) and piperidine (532 mg, 6.25 mmol) and reacted at 100 ° C. for 3 hours 30 minutes. Piperidine (517 mg, 6.07 mmol) was added thereto, and the mixture was heated at 100 ° C. again for 3 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (100 ml, dichloromethane: methanol = 10: 1-5: 1) to give compound (38D-A) (1500.8 mg, yield: 99%). (2) Preparation of 4-[(2R)-{2-acetylamino-2-carboxy) ethylthio}] methyl-5-oxo-5-phenylpentanoic acid (Compound 38D) Compound (38D-A) (576.0 mg, 1.99 mmol) and (R) -N-acetylcysteine (324.7 mg, 1.99 mmol) were dissolved in ethanol (5 ml) and the solution was heated to reflux for 4 hours. After cooling, the mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (100 ml, chloroform: methanol = 10: 1-3: 1) to give compound (38D) (417.4 mg, yield: 57%). Example 34 Preparation of (1R, 2S) -2- [N- (pantoyl--alanylamido) ethylthio] methyl-3-oxo-1-cyclopentanecarboxylic acid (Compound 1E) 500 ml of 100 ml of culture medium (2.0% glycerin, 1.0% glucose, 0.5% soybean meal, 0.3% peptone, 0.5% yeast extract, 0.2% calcium carbonate, 0.05% dipotassium phosphate and 0.05% magnesium sulfate; pH 7.0) It was put into a volumetric shake shake erlenmeyer flask and sterilized for 20 minutes at 120 degreeC in an autoclave. Strain NA32176 (FERM P-16372) platinum was inoculated into the medium and incubated for 2 days at 27 ° C. at 220 rpm. For main culture, medium (1.0% glucose, 4.0% starch syrup, 1.0% corn steep liquor, 0.2% yeast extract, 1.0% gluten milk, 0.00011% iron sulfate heptahydrate, 0.00064% copper sulfate pentahydrate, 0.00015% zinc sulfate 7 100 ml of hydrate, 0.00079% manganese chloride tetrahydrate, 0.0001% cobalt chloride and 0.2% calcium carbonate; pH 7.0) was taken and placed in a 500 ml volumetric rotary shake flask, sterilized for 20 minutes at 120 ° C. in an autoclave. One milliliter of the seed culture solution was inoculated into the main medium in the flask and incubated for 2 days at 27 ° C. at 220 rpm. The culture solution (10 L) was filtered by a conventional method to separate the filtrate and mycelium cake. After adjusting to pH 8 with 4N sodium hydroxide, the filtrate was added to a DIAION HP-20 column (1 L) and washed. Eluted with a straight slope from water (2 L) to 80% methanol (2 L). After removing the methanol, the pH of the elution fraction was adjusted to pH 2 with 1N hydrochloric acid and eluted with n-butanol. The n-butanol layer was concentrated under reduced pressure, and the residue (491 mg) was subjected to Sephadex LH-20 column chromatography (fai 3.5 x 90 cm, mobile phase: methanol). The obtained active fraction (267 mg) was dissolved in a mixed solution of ethyl acetate-water (1: 1), and this solution was subjected to centrifugal liquid-liquid distribution chromatography (volume 250 ml, 1500 rpm, flow rate 3 ml / min) (The lower phase of the mixture was previously seeded and used as the stationary phase). After washing with the upper liquid phase of the mixture, the active fractions were reversibly eluted by the lower phase to give crude active material (16 mg). The crude material was subjected to Sephadex LH-20 column chromatography (fai 1.8 × 85 cm, mobile phase: methanol) to give NA32176A (Compound E) (13 mg). The appearance, molecular weight, solubility, Rf value, UV absorption spectrum, IR absorption spectrum, 1 H-NMR spectrum, and 13 C-NMR spectrum of NA32176A (Compound 1E) purified as described above were measured. The physicochemical properties of NA32176A (Compound 1E) are as shown above. Example 35 Preparation of 4-oxo-4-phenyl-3- (1-piperidyl) methylbutyric acid (Compound 1F) Compound (1F) is described, for example, in J. Chem. Soc. (C), 2308 (1967). Example 36 Preparation of 4- (4-methylphenyl) -4-oxo-3- (1-piperidyl) methylbutyric acid (Compound 2F) Piperidine (1027 mg, 12.07 mmol) and 37% aqueous formaldehyde solution (0.98 ml, 12.07 mmol) were added to 4- (4-methylphenyl) -4-oxobutyric acid (2320 mg, 12.07 mmol) and the mixture was heated To a homogeneous state. Subsequently, the reaction solution was stirred at room temperature for 15 hours, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform: methanol = 20: 1-10: 1) to give compound (2F) (745 mg, yield: 22.6%). Example 37 Preparation of 4- (4-methoxyphenyl) -4-oxo-3- (1-piperidyl) methylbutyric acid (Compound 3F) Piperidine (851 mg, 10 mmol) and 37% aqueous formaldehyde solution (0.81 ml, 10 mmol) were added to 4- (4-methoxyphenyl) -4-oxobutyric acid (2080 mg, 10 mmol) and this mixture The reaction solution was stirred at room temperature for 3 hours, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (250 ml, chloroform: methanol = 20: 1-10: 1) to give compound (3F) (552 mg, yield: 19%). Example 38 Preparation of 4-oxo-4-phenyl-3- (1-pyrrolidinyl) methylbutyric acid (Compound 4F) Piperidine (1020 mg, 14.34 mmol) and 37% aqueous formaldehyde solution (1.16 ml) were added to 4-oxo-4-phenylbutyric acid (2555 mg, 14.34 mmol), and the mixture was heated to homogeneity. Subsequently, the reaction solution was stirred at room temperature for 10 hours and then concentrated under reduced pressure. A part of the residue (920 mg) was purified by silica gel column chromatography (90 ml, chloroform: methanol = 5: 1-2: 1) to give compound (4F) (372 mg, yield: 40%). Example 39 Preparation of 3- (4-morpholinyl) methyl-4-oxo-4-phenylbutyric acid (Compound 5F) Morpholine (3891 mg, 4.47 mmol) and 37% aqueous formaldehyde solution (0.37 g, 4.47 ml) were added to 4-oxo-4-phenylbutyric acid (797 mg, 4.47 mmol), and the mixture was heated to homogeneity. . Subsequently, the reaction solution was stirred at room temperature for 15 hours, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (200 ml, chloroform: methanol = 10: 1-2: 1) to give compound (5F) (510 mg, yield: 41%). Example 40 Preparation of 3- {1- (4-methylpiperazinyl)} methyl-4-oxo-4-phenylbutyric acid (Compound 6F) 1-methylpiperazinyl (349 mg, 3.51 mmol) and 37% aqueous formaldehyde solution (0.29 ml, 3.51 mmol) were added to 4-oxo-4-phenylbutyric acid (627 mg, 3.51 mmol) and the mixture was heated to It was made homogeneous. Subsequently, the reaction solution was stirred at room temperature for 15 hours, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (90 ml, butanol: acetic acid: water = 20: 1: 1) and Sephadex LH-20 (250 ml, 80% hydrated methanol) to give compound (6F) (251). mg, yield: 24.6%). Example 41 Preparation of 3- (diethylamino) methyl-oxo-4-phenylbutyric acid (Compound 7F) Diethylamine (300 mg, 4.10 mmol) and 37% aqueous formaldehyde solution (0.33 ml) were added to 4-oxo-4-phenylbutyric acid (730 mg, 4.10 mmol), and the mixture was heated to homogeneity. Subsequently, the reaction solution was stirred at room temperature for 16 hours and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (90 ml, chloroform: methanol = 10: 1-5: 1) to give compound (7F) (312 mg, yield: 28.9%). Example 42 Preparation of (1R, 2R) -3-oxo-2- (1-piperidyl) methyl-1-cyclopentanecarboxylic acid (Compound 8F) (1R, 2S) -2-[(2RS)-(2,3-O-isopropylidene) propylsulfonyl] methyl-3-oxo-cyclopentanecarboxylic acid (205 mg, 0.64 mmol) was acetone (3 ml), piperidine (55 mg, 0.64 mmol), methanol (2 ml) and 1N sodium hydroxide (0.45 ml) were added successively to the solution, and the mixture was stirred at room temperature for 20 hours before reaction. The liquid was concentrated under reduced pressure. The residue was purified by Sephadex LH-20 (250 ml, 80% hydrated methanol) to give compound (8F) (75 mg, yield: 52%). MS (FAB, POS) m / z: 226 (M + H) < + > Example 43 Preparation of 4-oxo-4- (3-pyridyl) -3- (1-piperidyl) methylbutyric acid (Compound 12F) (1) Preparation of Methyl 4-oxo-4- (3-pyridyl) butyrate (Compound 12F-A) Under nitrogen atmosphere, a solution of 3-pyridinecarboxyaldehyde (10.7 g, 100 mmol) of anhydrous dimethylformamide (20 ml) was added to anhydrous dimethylformamide (80 ml) of sodium cyanide (2.44 g, 50 mmol) at 30 ° C. To the solution was added dropwise over 30 minutes, stirred for 30 minutes and then to the reaction mixture was added dropwise a solution of methyl acrylate (8.6 g, 100 mmol) of anhydrous dimethylformamide (80 ml) over 1 hour, It stirred at 30 degreeC for 3 hours. Acetic acid (0.66 ml) and water (30 ml) were added to the reaction solution, and the mixture was concentrated under reduced pressure after stirring for 10 minutes. Water (360 ml) and chloroform (300 ml x 3) were added to the residue, and the obtained organic phase was washed with saturated aqueous sodium chloride solution (300 ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (650 ml, hexane: ethyl acetate = 1: 1: 1: 2) to give compound (12F-A) (7.87 mg, yield: 40.7%). (2) Preparation of 4-oxo-4- (3-pyridyl) butyric acid (Compound 12F-B) Compound (12F-A) (5.04 g, 26.11 mmol) was dissolved in methanol (60 ml), 1N sodium hydroxide (32 ml) was added to this solution, and the mixture was stirred at room temperature for 3 hours. 2N hydrochloric acid (16 ml) was then added to the reaction mixture, followed by concentration under reduced pressure. The residue was purified by silica gel column chromatography (250 ml, chloroform: methanol: acetic acid = 20: 1: 0.5) to give compound (12F-B) (3.13 g, yield: 66.9%). (3) Preparation of 4-oxo-4- (3-pyridyl) -3- (1-piperidyl) methylbutyric acid (Compound 12F) To compound (12F-B) (246 mg, 1.37 mmol) was added piperidine (140 mg, 1.64 mmol) and 37% formalin (0.133 ml, 1.64 mmol) and the mixture was stirred at 100 ° C. for 2 hours. Silica gel (1.8 g) was added to the reaction solution, concentrated, and the residue was purified by silica gel column chromatography (30 ml, chloroform: methanol: acetic acid = 10: 1: 0.5-10: 5: 3) Compound (12F) was obtained (300 mg, yield: 79%). Example 44 Preparation of 4- (2-furyl) -4-oxo-3- (1-piperidyl) methylbutyric acid (Compound 26F) (1) Preparation of Methyl 4- (2-furyl) -4-oxobutyrate (Compound 26F-A) 3-benzyl-5- (2-hydroxyethyl) -4-methylthiazolium chloride (1.0 g, 4 mmol) and triethylamine (2.02 g, 20 mmol) were dissolved in furfural (4.8 g, 50 mmol). To a solution of anhydrous ethanol (30 ml) was added and the mixture was stirred for 40 minutes at room temperature. Methyl acrylate (5.0 g, 50 mmol) was added to the mixture, which was then heated to reflux for 7 hours. The reaction solution was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (600 ml, hexane: ethyl acetate = 2: 1) to obtain compound (26F-A) (3430 mg, yield: 37.6). %). (2) Preparation of 4- (2-furyl) -4-oxobutyric acid (Compound 26F-B) To a solution obtained by adding compound (26F-A) (1820 mg, 10 mmol) to methanol (20 ml) was added 1N aqueous sodium hydroxide solution (10.5 ml), and the mixture was stirred at room temperature for 3 hours. After concentration under reduced pressure, the residue was separated by addition of water (30 ml) and ethyl acetate (30 ml). The aqueous phase was adjusted to pH 3.0 by adding 2N aqueous hydrochloric acid solution and then extracted with ethyl acetate (30 ml × 2). The organic phase was washed with saturated aqueous sodium chloride solution (50 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give compound (26F-B) (1445 mg, yield: 86%). (3) Preparation of 4- (2-furyl) -4-oxo-3- (1-piperidyl) methylbutyric acid (Compound 26F) To compound (26F-B) (1431 mg, 8.51 mmol) was added piperidine (797 mg, 9.36 mmol) and 37% formalin (0.76 ml, 9.36 mmol) and the mixture was stirred at rt for 4 days. Silica gel (4.5 g) was added to the reaction solution, and the residue was concentrated under reduced pressure, and then the residue was purified by silica gel column chromatography (100 ml, chloroform: methanol: acetic acid = 10: 1: 0.5-3: 1: 0.3) Compound (26F) was obtained (1325 mg, yield: 62.5%). Example 45 Preparation of 3- (1-pyridyl) methyl-4-oxo-4- (4'-trifluoromethylphenyl) butyric acid (Compound 9F) (1) Preparation of 4 '-(trifluoromethyl) acidnamic acid (Compound 9F-A) A mixture of 4 ′-(trifluoromethyl) acetophenone (2500.5 mg, 13.29 mmol) glycolic acid monohydrate (1223.3 mg, 13.29 mmol) was reacted at 95 ° C. for 1 hour with aspirator. Glycolic acid monohydrate (439.5 mg, 477 mmol) was added thereto and reacted at 95 ° C for 2 hours while being aspirated with an aspirator. After cooling to room temperature, 20 ml of 5% potassium carbonate was added to the reaction solution, and the mixture was extracted twice with ethyl acetate. The aqueous layer was adjusted to pH 1 with 4N hydrochloric acid and then extracted twice with ethyl acetate. The extract was washed with water and then with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was dissolved in acetic acid (10 ml) and concentrated hydrochloric acid (0.5 ml) was added to this solution. The mixture was heated to reflux for 7 hours, and the reaction solution was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, and this solution was washed with water and then with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was recrystallized in hexane-ethyl acetate to give compound (9F-A) (1554.5 mg, yield: 48%). (2) Preparation of 4- (4 '-(trifluoromethylphenyl) -butyric acid (Compound 9F-B) Compound (9F-A) (1036.9 mg, 4.25 mmol) was dissolved in acetic acid (9 ml) and water (2 ml), and zinc powder (320.1 mg, 4.89 mmol) was added to this solution, and the mixture was stirred at room temperature. Stirred for time. After filtration through celite, the filtrate was concentrated under reduced pressure. The residue was purified by suspension in ethyl acetate to give compound (9F-B) (1111.0 mg, yield: 100%). (3) Preparation of 3- (1-piperidyl) methyl-4-oxo-4- (4 '-(trifluoromethylphenyl) butyric acid (Compound 9F) Compound (9F-B) (1005.7 mg, 4.08 mmol) was dissolved in dimethylsulfoxide (10 ml), and an aqueous solution of formalin (507 mg, 6.25 mmol) and piperidine (532 mg, 6.25 mmol) were added thereto. It was. The mixture was reacted at 100 ° C for 24 hours, and after cooling with ice, the precipitate was removed by filtration. The filtrate was separated with water and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined, washed with saturated aqueous sodium chloride solution and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (200 ml, chloroform: methanol = 5: 1-1: 2) to give compound (9F) (312.5 mg, yield: 22%). Example 46 Preparation of 2-Methyl-4-oxo-4-phenyl-3- (1-piperazinyl) methylbutyric acid (Compound 41F) 2-Methyl-4-oxo-4-phenylbutyric acid (1000.5 mg, 5.21 mmol) is suspended in an aqueous formalin solution (507 mg, 6.25 mmol) and piperidine (532 mg, 6.25 mmol) and ethanol (6) in this suspension. ml) was added. After reacting for 40 minutes at 100 DEG C, the crystals obtained by filtration in hot state were dried to give compound (41F) (529.2 mg, yield: 35%). MS (FAB, POS) m / z: 290 (M + H) < + > Example 47 Preparation of 4- (1-piperazinyl) methyl-5-oxo-5-phenylpentanoic acid (Compound 42F) 4-benzoylbutyric acid (1000.9 mg, 5.21 mmol) was suspended in an aqueous formalin solution (507 mg, 6.25 mmol) and piperidine (532 mg, 6.25 mmol) and reacted at 100 ° C. for 3 hours 30 minutes. Piperidine (517 mg, 6.07 mmol) was added thereto and reacted at 100 ° C. for an additional 3 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (100 ml, dichloromethane: L = 10: 1-5: 1) to give compound (42F) (1500.8 mg, yield: 99%). Test Example 1 Influence of Nerve Cell-like Neurite Elongation of Compounds of the Invention on PC12 Cells The effects of the compounds of the present invention are described in Green et al., Ann. Rev. Neurosci., 3, 353, 1980] was evaluated by a variation of the method described in the evaluation of the morphological changes of the PC12 cells and their extent. That is, PC12 cells were seeded at about 100,000 cells / ml in Dulbecco's modified Eagle's medium supplemented with 10% fetal bovine serum and 10% horse serum. These cells were incubated at 37 ° C. in 5% CO 2 using collagen coated 96 well multiplates. Under these conditions, one day after the test compound was added to each well, the morphology of the cells was observed under a microscope. The minimum effective dose (MED, g / ml) in which each compound induces neuronal-like neurite extension for PC12 cells is shown in Table 2 below. TABLE 2 Minimum effective amount for neural cell-like neurite elongation induced on PC12 cells Compound no.MED (g / ml)Compound no.MED (g / ml)Compound no.MED (g / ml) 1A3.22C6.338D6.3 2A3.21D251E1.2 6A252D131F1.6 1B3.23D0.82F3.1 2B1.64D133F3.1 3B3.25D504F1.6 4B3.26D505F3.1 5B0.87D136F3.1 6B1.68D6.37F1.6 7B3.19D508F1.6 8B0.810D10012F3.1 9B6.311D1326F3.1 13B1.612D139F0.8 14B3.113D1341F6.3 15B3.132D3.142F1.6 The compounds of the present invention or pharmacologically acceptable salts thereof exhibit potent neuronal differentiation promoting action. Therefore, pharmaceutical compositions containing these compounds or pharmacologically acceptable salts thereof are useful as promoters for neuronal differentiation, and can also be effectively applied as a medicament for treating central or horse follicular neuropathy.
权利要求:
Claims (73) [1" claim-type="Currently amended] Cyclopentanone derivatives represented by the following general formula [1A] or a pharmacologically acceptable salt thereof: In the above formula, X A is O, S, SO, SO 2 or NH; Y A is a substituted or unsubstituted linear or branched aliphatic hydrocarbon group having 1 to 20 carbon atoms or a substituted or unsubstituted monocyclic aromatic heterocyclic or aromatic hydrocarbon group having 3 to 6 carbon atoms; Z1 A , Z2 A and Z3 A may be the same or different, and each independently represent a carboxyl group or a group derived therefrom, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, a hydroxy group or a group derived therefrom, an amino group Or a group derived therefrom, a sulfonate group or a group derived therefrom, a phosphate group or a group derived therefrom, a monocyclic heteroaryl group, halogen or hydrogen, or Z 2 A and Z 3 A are bonded together to be substituted or unsubstituted To form an aromatic hydrocarbon or aromatic heterocycle of the ring; And Z1 A is a carboxyl group or group derived therefrom, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, a hydroxy group or a group derived therefrom, an amino group or a group derived therefrom, halogen or hydrogen, provided that Z2 A and When Z 3 A is all hydrogen, Z 1 A is a hydroxy group or a group derived therefrom, an amino group or a group derived therefrom, a sulfonate group or a monocyclic aromatic heterocyclic ring, halogen or hydrogen, and Y A is substituted with 1 to 6 carbon atoms. Or an unsubstituted linear or branched aliphatic hydrocarbon group; Except for the following cases (1) to (7): (1) when Z1 A and Z2 A are hydrogen, X A is S, Y A is a methyl group or benzyl group, Z3 A is a methoxycarbonyl group, (2) when Z1 A and Z2 A are hydrogen, X A is O or N, Y A is a benzyl group, Z3 A is a carboxy group, methoxycarbonyl group or ethoxycarbonyl group, (3) X A is N or O, Z 1 A and Z 3 A are hydrogen, Z 2 A is a carboxy group, methoxycarbonyl group, (4) X A is O, Z 1 A is a hydroxyl group or a group derived therefrom, Z 2 A is a hydrogen, Z 3 A is an amino group or a group derived therefrom, (5) X A is S, Y1 A is a phenyl group, Z1 A is a dimethoxymethyl group, Z2 A and Z3 A are hydrogen, (6) X A is O, Y 1 A is a methyl group, Z 1 A is a 1-methoxy-1-phenylthiomethyl group, Z 2 A and Z 3 A are hydrogen, (7) Z 1 A is S, SO or SO 2 , Z 2 A is a hydroxy group or a group derived therefrom, Z 3 A is hydrogen. 2,3-di-substituted cyclopentanone derivatives of the general formula [1B] or pharmacologically acceptable salts thereof: In the above formula, X B is O, S, SO, SO 2 or NH; Y B is Unsubstituted or substituted straight-chain or branched aliphatic hydrocarbon group having 7 to 20 carbon atoms, Linear or branched aliphatic hydrocarbon groups having 1 to 6 carbon atoms, Wherein at least one hydrogen may be substituted with COW1 (wherein W1 is an unsubstituted or substituted aromatic heterocycle or a saturated heterocycle), at least one hydrogen may be further substituted with a group derived from an amino group, or at least one hydrogen is NHCOV1 (where V1 is an alkyl group having 2 to 5 carbon atoms having 4 to 11 halogen atoms), and at least one hydrogen may be further substituted with a carboxy group or a group derived therefrom, or at least one hydrogen is substituted or unsubstituted. Substituted with a cyclic aromatic heterocycle, and at least one hydrogen may be further substituted with an amino group or a group derived therefrom; Or a substituted or unsubstituted monocyclic aromatic heterocyclic ring or aromatic heterocyclic ring having 3 to 6 carbon atoms; Z B is a carboxyl group or a group derived therefrom, a sulfonate group or a group derived therefrom, a phosphate group or a group derived therefrom, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, a hydroxy group, OR1 (where R1 is Unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, unsubstituted or substituted acyl group having 1 to 5 carbon atoms, NHCOR2 (where R2 is unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), NHSO 2 R2 '(where R2' is an unsubstituted or substituted alkyl or phenyl group having 1 to 4 carbon atoms), a monocyclic aromatic heterocyclic ring, halogen or hydrogen. Cyclopentenone derivatives of the general formula [1C] or pharmacologically acceptable salts thereof: In the above formula, Ring A has one double bond conjugated with oxo; X C is O, S, SO, SO 2 or NH; Y C is a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 6 carbon atoms, or a substituted or unsubstituted monocyclic aromatic heterocyclic or aromatic hydrocarbon group having 3 to 6 carbon atoms; Z 1 C , Z 2 C and Z 3 C may be the same or different, and each independently represent a carboxy group or a group derived therefrom, a hydroxy group or a group derived therefrom, an amino group or a group derived therefrom, or a substitution of 1 to 4 carbon atoms. Or an unsubstituted alkyl or alkenyl group, a monocyclic aromatic heterocyclic ring, a halogen atom or hydrogen; Provided that when X C is O or NH, Z 1 C and Z 3 C are not hydrogen, and Z 2 C is not hydrogen or a hydroxy group or a group derived therefrom. Ketone derivatives of the general formula [1D] or pharmacologically acceptable salts thereof: In the above formula, A D is an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 4 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon, a heterocyclic ring or a saturated heterocyclic ring; B D is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 4 carbon atoms; or A D and B D are bonded together to form an unsubstituted or substituted cycloalkane-1-one ring having 3 to 7 carbon atoms (excluding 5 carbon atoms); X D is O, S, SO, SO 2 or NH; Y D is a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 6 carbon atoms or a substituted or unsubstituted monocyclic aromatic heterocyclic or aromatic hydrocarbon group having 3 to 6 carbon atoms; Z D is a carboxyl group or group derived therefrom, an unsubstituted or substituted alkyl group or alkenyl group, hydroxy group or group derived therefrom, an amino group or a group derived therefrom, a sulfonate group or derived therefrom Group, phosphate group or group derived therefrom, monocyclic aromatic heterocycle, halogen or hydrogen; However, when A D and B D are bonded together to form a cyclobutane ring, the following (1) to (4) are excluded: (1) X D is O, Y D is a methyl group, n-octyl group or n-hexadecyl group, and Z D is a methoxycarbonyl group; (2) X D is O, Y D is a benzyl group, and Z D is a benzyloxymethyl group; (3) X D is O, Y D is p-methoxybenzyl group, and Z D is p-methoxybenzyloxymethyl group; (4) When X D is O, Y D is trityl group, Z D is trityloxymethyl group, or A D is an unsubstituted benzene ring and B D is hydrogen, X D is S, Y D is methyl, ethyl Or isopropyl group and Z D is a carboxy group. Compound of formula [1E] or a pharmacologically acceptable salt thereof: Β-di-substituted aminoketone derivatives of the general formula [1F] or pharmacologically acceptable salts thereof: In the above formula, A F is an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 4 carbon atoms, or an unsubstituted or substituted aromatic hydrocarbon ring, an aromatic heterocycle, or a saturated heterocycle; B F is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 4 carbon atoms; A F and B F are bonded together to form an unsubstituted or substituted cycloalkane-1-one ring having 3 to 7 carbon atoms or fused with an aromatic hydrocarbon or aromatic heterocycle, or cycloalkane-1 having 3 to 7 carbon atoms. -Form a warm ring; X F and Y F are each an unsubstituted or substituted linear or branched aliphatic hydrocarbon group having 1 to 10 carbon atoms, or X F and Y F are bonded directly to each other or through a hetero atom to form an unsubstituted or substituted group. To form a heterocycle; Z F is a carboxyl group or group derived therefrom, an unsubstituted or substituted alkyl group or alkenyl group, hydroxy group or group derived therefrom, an amino group or group derived therefrom, a sulfonate group or derived therefrom Group, phosphate group or group derived therefrom, monocyclic aromatic heterocycle or halogen; However, when A F is an unsubstituted benzene ring, except that B F is hydrogen, X F and Y F are directly bonded to each other to form a piperidine ring, and Z F is a carboxy group. [2" claim-type="Currently amended] The cyclopentanone derivative or pharmacologically acceptable salt thereof according to claim 1, wherein the general formula [1A] is defined as follows: In the above formula [1A], X A is O, S, SO or SO; Y A is a straight or branched aliphatic hydrocarbon group having 1 to 20 carbon atoms, wherein at least one hydrogen atom is substituted with a carboxyl group or a group derived therefrom or an amino group or a group derived therefrom; Z1 A , Z2 A and Z3 A may be the same or different, and each independently represent a carboxyl group or a group derived therefrom, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, a hydroxy group or a group derived therefrom, an amino group Or a group derived therefrom, a monocyclic aromatic heterocycle, halogen or hydrogen, or Z2 A and Z3 A combine together to form a substituted or unsubstituted aromatic hydrocarbon or aromatic heterocycle; And Z 1 A is a carboxyl group or group derived therefrom, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, a hydroxyl group or a group derived therefrom, an amino group or a group derived therefrom, halogen or hydrogen. [3" claim-type="Currently amended] The cyclopentanone derivative or pharmacologically acceptable salt thereof according to claim 2, wherein the general formula [1A] is defined as follows: In the above formula [1A], X A is S; Y A is a linear or branched aliphatic hydrocarbon group having 1 to 6 carbon atoms, wherein at least one hydrogen is a carboxy group, COOR1 (where R1 is a substituted or unsubstituted alkyl, alkenyl or alkynyl group having 1 to 4 carbon atoms) , COW1 (where W1 is a heterocyclic unsubstituted or substituted with a carboxyl group or a group derived therefrom) or NR2R3 (wherein R2 and R3 may each be the same or different, each independently hydrogen, unsubstituted with 1 to 4 carbon atoms or A substituted alkyl group or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms; Z1 A , Z2 A and Z3 A may each be the same or different, each independently represent a carboxy group, COOR4 (where R4 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), CONR5R6 (where R5 and R6 are each the same) Or may be different from each other independently hydrogen or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, a cyano group, a hydroxy group, OR7 (where R7 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or carbon atoms) NR8R9 (where R8 and R9 may each be the same or different), and each independently hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or a carbon atom having 1 to 5 carbon atoms; 5 unsubstituted or substituted acyl group, CH 2 OR10 (where R10 is hydrogen, unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or unsubstituted or substituted acyl group having 1 to 5 carbon atoms), Chlorine, Fluorine Represents hydrogen; Z2 A and Z3 A combine together to form a substituted or unsubstituted aromatic hydrocarbon; Z1 A is a carboxy group, COOR4 (where R4 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), CONR5R6 (where R5 and R6 may each be the same or different, and are each independently hydrogen or carbon atoms having 1 to 4 carbon atoms) Substituted or unsubstituted alkyl group), cyano group, hydroxy group, OR7 (where R7 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms), NR8R9 (Wherein R8 and R9 may each be the same or different, and each independently represent hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms), CH 2 OR10 R10 is hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms, and chlorine, fluorine or hydrogen. [4" claim-type="Currently amended] The cyclopentanone derivative of the general formula [1A] or a pharmacologically acceptable salt thereof according to claim 3, wherein: In the general formula [1A] above, X A is S; Y A is a linear aliphatic hydrocarbon group having 1 to 6 carbon atoms, wherein at least two hydrogens are a carboxy group, COOR1 '(where R1' is an alkyl group having 1 to 4 carbon atoms, an alkenyl group or an alkynyl group), and COW2 (where W2 Is substituted with either COOR11 (R11 is a saturated heterocyclic ring unsubstituted or substituted with an alkyl group having 1 to 4 carbon atoms) or NHCOR12 (where R12 is an alkyl group having 1 to 4 carbon atoms); Z1 A , Z2 A and Z3 A may each be the same or different and each independently represent a carboxy group, COOR4 '(where R4' is an alkyl group having 1 to 4 carbon atoms), a hydroxy group, OCOR13 (where R13 is 1 to 4 carbon atoms) Alkyl group), CH 2 0R 10 ′ where R 10 ′ is hydrogen, an alkyl group having 1 to 4 carbon atoms, or an acyl group having 1 to 5 carbon atoms; Z 2 A and Z 3 A are bonded together to form a benzene ring unsubstituted or substituted with an alkyl group having 1 to 4 carbon atoms, an alkyloxy group having 1 to 4 carbon atoms, a nitro group, a trifluoromethyl group or a halogen; Z1 A is a carboxy group, COOR4 '(where R4' is an alkyl group having 1 to 4 carbon atoms), a hydroxy group, OCOR13 (where R13 is an alkyl group having 1 to 4 carbon atoms), CH 2 0R10 '(where R10' is hydrogen, An alkyl group having 1 to 4 carbon atoms or an acyl group having 1 to 5 carbon atoms) or hydrogen. [5" claim-type="Currently amended] The cyclopentanone derivative of the general formula [1A] or a pharmacologically acceptable salt thereof according to claim 4, wherein: In the general formula [1A] above, X A is S; Y A is a linear aliphatic hydrocarbon group having 1 to 6 carbon atoms, Wherein one hydrogen is substituted with a carboxy group, methoxycarbonyl group, COW3, where W3 may be substituted or unsubstituted with a methoxycarbonyl group as a pyrrolidine, piperidine, azetidine, morpholine or piperazine ring, and another One hydrogen is substituted with an acetylamino group; Z1 A , Z2 A and Z3 A may each be the same or different and each independently represent a carboxy group, methoxycarbonyl group, hydroxy group, acetyloxymethyl group, hydroxymethyl group or hydrogen; or Z2 A and Z3 A combine together to form an unsubstituted benzene ring; Z1 A is a carboxy group, methoxycarbonyl group, hydroxy group, acetyloxymethyl group, hydroxymethyl group or hydrogen. [6" claim-type="Currently amended] The cyclopentanone derivative of the general formula [1A] or a pharmacologically acceptable salt thereof according to claim 5, wherein the cyclopentanone derivative is selected from the group consisting of substituents defined as follows: In the general formula [1A] above, (I) X A is S, Y A is 2-acetylamino-2-carboxyethyl, Z1 A and Z3 A are hydrogen, and Z2 A is a carboxy group; (II) X A is S, Y A is 2-acetylamino-2-methoxycarbonylethyl, Z1 A and Z3 A are hydrogen, and Z2 A is a carboxy group; (III) X A is S, Y A is 2-acetylamino-2-carboxyethyl, Z1 A and Z3 A are hydrogen, and a Z2 A hydroxy group; (IV) X A is S, Y A is 2-acetylamino-3-oxo-3- {1- (2-methoxycarbonyl) pyrrolidinyl} propyl, Z1 A and Z3 A are hydrogen, and Z2 A A hydroxy group; (V) X A is S, Y A is 2-acetylamino-2-methoxycarbonylethyl, Z 2 A and Z 3 A are bonded together to form an unsubstituted benzene ring, and Z 1 A is a carboxy group; And (VI) X A is S, Y A is 2-acetylamino-2-carboxyethyl, Z2 A and Z3 A are bonded together to form an unsubstituted benzene ring, and Z1 A is a carboxy group. [7" claim-type="Currently amended] The 2,3-di-substituted cyclopentanone derivative of the general formula [1B] or a pharmacologically acceptable salt thereof according to claim 1, wherein In the above general formula [1B], X B is S, O or SO; Y B is a straight or branched aliphatic hydrocarbon group having 7 to 20 carbon atoms, wherein at least one hydrogen may be optionally substituted with a carboxyl group or a group derived therefrom or an amino group or a group derived therefrom; Z B is a carboxy group, COOR3 (where R3 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), CH 2 OR4 (where R4 is hydrogen or an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), or CH 2 OCOR5 (where R5 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms). [8" claim-type="Currently amended] The 2,3-di-substituted cyclopentanone derivative of the general formula [1B], or a pharmacologically acceptable salt thereof according to claim 7, wherein: In the above general formula [1B], X B is S; Y B is a linear aliphatic hydrocarbon group having 7 to 20 carbon atoms (where at least two hydrogens are a carboxy group, COOR6 (where R6 is an alkyl group having 1 to 4 carbon atoms, an alkenyl group or an alkynyl group) or NR7R8 (where R7 and R8 are the same) May be different from each other, and are each independently substituted with hydrogen, an alkyl group having 1 to 4 carbon atoms or an acyl group having 1 to 5 carbon atoms), Z B is a carboxy group, methoxycarbonyl group, hydroxymethyl group or acetyloxymethyl group. [9" claim-type="Currently amended] The 2,3-di-substituted cyclopentanone derivative of the general formula [1B] or a pharmacologically acceptable salt thereof according to claim 8, wherein: In the above general formula [1B], X B is S; Y B is 11-acetylamino-11-carboxy-n-undecyl, Z B is a carboxy group. [10" claim-type="Currently amended] The 2,3-di-substituted cyclopentanone derivative of the general formula [1B] or a pharmacologically acceptable salt thereof according to claim 1, wherein In the above general formula [1B], X B is S, O or SO; Y B is a linear or branched aliphatic hydrocarbon group having 1 to 6 carbon atoms, and at least one hydrogen is COW2 {where W2 is a saturated or unsubstituted or substituted with a hydroxyalkyl group, phenyl group or carboxy group having 1 to 4 carbon atoms Heterocyclic ring, COOR9 (wherein R9 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), and at least another hydrogen is NR10R11, where R10 and R11 may be the same or different, and each independently Hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms; Z B is a carboxy group, COOR3 (where R3 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), CH 2 0R4 (where R4 is hydrogen or an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), or CH 2 0COR 5, wherein R 5 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms. [11" claim-type="Currently amended] The 2,3-di-substituted cyclopentanone derivative of the general formula [1B] or a pharmacologically acceptable salt thereof according to claim 10, wherein: In the above general formula [1B], X B is S; Y B is a linear or branched aliphatic hydrocarbon group having 1 to 6 carbon atoms (wherein one hydrogen is COW3 (wherein W3 is substituted with a carboxyl group, methoxycarbonyl group, 2-hydroxyethyl group, phenyl group or tert-butoxycarbonyl group or May be unsubstituted, substituted with 1-azetidinyl, 1-piperidyl, 1-pyrrolidinyl, 1-piperazinyl or 4-morpholinyl group, and the other hydrogen is NHCOR12, where R12 is Substituted with an alkyl group of 1 to 4 carbon atoms; Z B is a carboxy group, methoxycarbonyl group, hydroxymethyl group or acetyloxy group. [12" claim-type="Currently amended] 12. The 2,3-di-substituted cyclopentanone derivative of the general formula [1B] as defined below, or a pharmacologically acceptable salt thereof: In the above general formula [1B], X B is S; Y B is 2-acetylamino-3-oxo-3- (1-pyrrolidinyl) propyl, 2-acetylamino-3- {1- (2-methoxycarbonyl) pyrrolidinyl} -3-oxopropyl , 2-acetylamino-3-oxo-3- (1-piperidyl) propyl, 2-acetylamino-3- (4-morpholinyl) -3-oxopropyl, 2-acetylamino-3- {1 -(2-methoxycarbonyl) azetidinyl} -3-oxopropyl, 2-acetylamino-3-oxo-3- (1-piperazinyl) propyl, 2-acetylamino-3- [1- { 4- (2-hydroxyethyl) piperazinyl}]-3-oxopropyl, 2-acetylamino-3- {1- (4-phenylpiperazinyl)}-3-oxopropyl or 2-acetylamino- 3- {1- (4-tert-butoxycarbonylpiperazinyl)}-3-oxopropyl; Z B is a carboxyl group or a methoxycarbonyl group. [13" claim-type="Currently amended] The 2,3-di-substituted cyclopentanone derivative of the general formula [1B] or a pharmacologically acceptable salt thereof according to claim 1, wherein In the above general formula [1B], X B is S, O or SO; Y B is a linear or branched aliphatic hydrocarbon group having 1 to 6 carbon atoms, wherein at least one hydrogen is substituted with NHCOV1 (where V1 is an alkyl group having 2 to 5 carbon atoms and 4 to 11 halogen atoms), and at least The other hydrogen may be further substituted with a carboxy group or COOR 13, wherein R 13 is an unsubstituted or substituted alkyl, alkenyl or alkynyl group having 1 to 4 carbon atoms. Z B is a carboxy group, COOR3 (where R3 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), CH 2 0R4 (where R4 is hydrogen or an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), or CH 2 0COR 5, wherein R 5 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms. [14" claim-type="Currently amended] The 2,3-di-substituted cyclopentanone derivative of the general formula [1B] or a pharmacologically acceptable salt thereof according to claim 13, wherein: In the above general formula [1B], X B is S; Y B is a linear aliphatic hydrocarbon group having 1 to 6 carbon atoms, where one hydrogen is substituted with NHCOV2 (where V2 is an alkyl group having 2 to 5 carbon atoms and 4 to 11 halogen atoms), and the other hydrogen is Is further substituted with a carboxy group or COOR13 'wherein R13' is an alkyl, alkenyl or alkynyl group having 1 to 4 carbon atoms. Z B is a carboxy group, methoxycarbonyl group, hydroxymethyl group or acetyloxymethyl group. [15" claim-type="Currently amended] The 2,3-di-substituted cyclopentanone derivative of the general formula [1B] or a pharmacologically acceptable salt thereof according to claim 14, wherein: In the above general formula [1B], X B is S; Y B is 2-carboxy-2- (pentafluoropropionyl) aminoethyl; Z B is a carboxy group or a hydroxymethyl group. [16" claim-type="Currently amended] The 2,3-di-substituted cyclopentanone derivative of the general formula [1B] or a pharmacologically acceptable salt thereof according to claim 1, wherein In the above general formula [1B], X B is S, O or SO; Y B is a linear or branched aliphatic hydrocarbon group having 1 to 6 carbon atoms (where at least one hydrogen is substituted with a substituted or unsubstituted monocyclic heterocycle, and at least another hydrogen is NR15R16 (where R15 and R16 are each May be the same as or different from each other, and are each independently substituted with hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or an acyl group having 1 to 5 carbon atoms). Z B is a carboxy group, COOR3 (where R3 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), CH 2 0R4 (where R4 is hydrogen or an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), or CH 2 0COR 5, wherein R 5 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms. [17" claim-type="Currently amended] The 2,3-di-substituted cyclopentanone derivative of the general formula [1B] or a pharmacologically acceptable salt thereof according to claim 16, wherein: In the above general formula [1B], X B is S; Y B is a linear aliphatic hydrocarbon group having 1 to 4 carbon atoms (where one hydrogen is substituted with a pyridine ring or 5-tetrazolyl unsubstituted or substituted with an alkyl group having 1 to 4 carbon atoms, and the other hydrogen is May be further substituted with NHCOR 17, wherein R 17 is an alkyl group having 1 to 4 carbon atoms. Z B is a carboxy group, methoxycarbonyl group, hydroxymethyl group or acetyloxymethyl group. [18" claim-type="Currently amended] 18. The 2,3-di-substituted cyclopentanone derivative of the general formula [1B] as defined below, or a pharmacologically acceptable salt thereof: In the above general formula [1B], X B is S; Y B is 3- (3-pyridyl) propyl, 3- {3- (1-methylpyridinium iodide)} propyl or 2-acetylamino-2- (5-tetrazolyl) ethyl; Z B is a carboxyl group or a methoxycarbonyl group. [19" claim-type="Currently amended] The cyclopentenone derivative of the general formula [1C] or a pharmacologically acceptable salt thereof according to claim 1, wherein In the above general formula [1C], Ring A forms an oxo conjugated double bond with carbon atoms bonded to CH 2 -X C -Y C ; X C is S, O or SO; Y C is an aliphatic hydrocarbon group having 1 to 6 carbon atoms, wherein at least one hydrogen is substituted with a carboxyl group or a group derived therefrom, an amino group or a group derived therefrom, or a hydroxy group or a group derived therefrom; Z 1 C , Z 2 C and Z 3 C may each be the same or different, and each independently represent a carboxyl group or a group derived therefrom, a hydroxy group or a group derived therefrom or an amino group or a group derived therefrom, or a substitution of 1 to 4 carbon atoms. Or an unsubstituted alkyl or alkenyl group, a monocyclic aromatic heterocycle, halogen or hydrogen. [20" claim-type="Currently amended] The cyclopentenone derivative of the general formula [1C] or a pharmacologically acceptable salt thereof according to claim 19, wherein: In the above general formula [1C], Ring A forms an oxo conjugated double bond with carbon atoms bonded to CH 2 -X C -Y C ; X C is S, O or SO; Y C is an aliphatic hydrocarbon group having 1 to 6 carbon atoms (where at least one hydrogen is a carboxy group, COOR1 (where R1 is a substituted or unsubstituted alkyl or alkenyl group having 1 to 4 carbon atoms), CONR2R3 (where R2 and R3, respectively) May be the same as or different from each other, and each independently hydrogen or an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, COW (where W is a carboxyl group or a group derived therefrom, or an amino group or a group derived therefrom) Or unsubstituted heterocyclic ring, NR4R5 (wherein R4 and R5 may each be the same or different, and each independently hydrogen, unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or unsubstituted or substituted with 1 to 5 carbon atoms) OR6 (where R6 is hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms) Hwandoem shown below); Z 1 C , Z 2 C and Z 3 C are each independently a carboxyl group, COOR 7 (where R 7 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), CONR 8 R 9 (where R 8 and R 9 may be the same or different, respectively, independently) Hydrogen or a C1-4 unsubstituted or substituted alkyl group), a cyano group, CH 2 OR10 (where R10 is hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or 1 to 5 carbon atoms) Unsubstituted or substituted acyl group, hydroxy group, OCOR11 (where R11 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), NR12R13 (where R12 and R13 may each be the same or different, each independently hydrogen , An unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms), 5-tetrazolyl, chlorine, fluorine or hydrogen. [21" claim-type="Currently amended] The cyclopentenone derivative of the general formula [1C] or a pharmacologically acceptable salt thereof according to claim 20, wherein: In the above general formula [1C], Ring A forms an oxo conjugated double bond with carbon atoms bonded to CH 2 -X C -Y C ; X C is S; Y C is an aliphatic hydrocarbon group of 1 to 6 carbon atoms (where at least two hydrogens are carboxyl groups, COOR1 '(where R1' is an alkyl or alkenyl group of 1 to 4 carbon atoms), NHCOR14 (where R14 is hydrogen fluorine) Optionally substituted with an alkyl group having 1 to 4 carbon atoms), a hydroxy group, or OCOR15, wherein R15 is substituted with an alkyl group having 1 to 4 carbon atoms; Z1 C , Z2 C and Z3 C are each a carboxy group, COOR7 '(where R7' is an alkyl group having 1 to 4 carbon atoms), or CH 2 OR10 '(where R10' is hydrogen or an acyl group having 1 to 5 carbon atoms) Im). [22" claim-type="Currently amended] The cyclopentenone derivative of the general formula [1C] or a pharmacologically acceptable salt thereof according to claim 21, wherein: In the above general formula [1C], Ring A forms an oxo conjugated double bond with carbon atoms bonded to CH 2 -X C -Y C ; X C is S; Y C is 2-acetylamino-2-carboxyethyl; Z 1 C or Z 2 C is a hydroxyl group, and the rest of Z 1 C , Z 2 C and Z 3 C are all hydrogen. [23" claim-type="Currently amended] The cyclopentenone derivative of the general formula [1C] or a pharmacologically acceptable salt thereof according to claim 1, wherein In the above general formula [1C], Ring A forms an oxo conjugated double bond without containing carbon atoms bonded to CH 2 -X C -Y C ; X C is S, O or SO; Y C is an aliphatic hydrocarbon group having 1 to 6 carbon atoms, wherein at least one hydrogen is substituted with a carboxyl group or a group derived therefrom or an amino group or a group derived from or a hydroxy group or a group derived therefrom, Z 1 A , Z 2 A and Z 3 A are each a carboxyl group or a group derived therefrom, an unsubstituted or substituted alkyl or alkenyl group, a hydroxy group or a group derived therefrom, an amino group or a group derived therefrom, having 1 to 4 carbon atoms, Monocyclic aromatic heterocycle, halogen or hydrogen. [24" claim-type="Currently amended] The cyclopentenone derivative of the general formula [1C] or a pharmacologically acceptable salt thereof according to claim 23, wherein: In the above general formula [1C], Ring A forms an oxo conjugated double bond without containing carbon atoms bonded to CH 2 -X C -Y C ; X C is S, O or SO; Y C is an aliphatic hydrocarbon group having 1 to 6 carbon atoms (where at least one hydrogen is a carboxy group, COOR1 (where R1 is a substituted or unsubstituted alkyl or alkenyl group having 1 to 4 carbon atoms), CONR2R3 (where R2 and R3, respectively) May be the same as or different from each other, and each independently hydrogen or an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, COW (where W is a carboxyl group or a group derived therefrom, or an amino group or a group derived therefrom) Or unsubstituted heterocyclic ring, NR4R5 (wherein R4 and R5 may each be the same or different, and each independently hydrogen, unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or unsubstituted or substituted with 1 to 5 carbon atoms) OR6 (where R6 is hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms) Hwandoem shown below); Z 1 C , Z 2 C and Z 3 C are each independently a carboxyl group, COOR 7 (where R 7 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), CONR 8 R 9 (where R 8 and R 9 may be the same or different, respectively, independently) Hydrogen or a C1-4 unsubstituted or substituted alkyl group), a cyano group, CH 2 OR10 (where R10 is hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or 1 to 5 carbon atoms) Unsubstituted or substituted acyl group, hydroxy group, OCOR11 (where R11 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), NR12R13 (where R12 and R13 may each be the same or different, each independently hydrogen , An unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms), 5-tetrazolyl, chlorine, fluorine or hydrogen. [25" claim-type="Currently amended] The cyclopentenone derivative of the general formula [1C] or a pharmacologically acceptable salt thereof according to claim 24, wherein: In the above general formula [1C], Ring A forms an oxo conjugated double bond without containing carbon atoms bonded to CH 2 -X C -Y C ; X C is S; Y C is an aliphatic hydrocarbon group of 1 to 6 carbon atoms (where at least two hydrogens are carboxyl groups, COOR1 '(where R1' is an alkyl or alkenyl group of 1 to 4 carbon atoms), NHCOR14 (where R14 is hydrogen fluorine) Optionally substituted with an alkyl group having 1 to 4 carbon atoms), a hydroxy group, or OCOR15, wherein R15 is substituted with an alkyl group having 1 to 4 carbon atoms; Z1 C , Z2 C and Z3 C are each a carboxy group, COOR7 '(where R7' is an alkyl group having 1 to 4 carbon atoms), or CH 2 OR10 '(where R10' is hydrogen or an acyl group having 1 to 5 carbon atoms) Im). [26" claim-type="Currently amended] The cyclopentenone derivative of the general formula [1C] or a pharmacologically acceptable salt thereof according to claim 25, wherein: In the above general formula [1C], Ring A forms an oxo conjugated double bond without containing carbon atoms bonded to CH 2 -X C -Y C ; X C is S; Y C is 2-acetylamino-2-carboxyethyl; Z1 C , Z2 C and Z3 C are all hydrogen. [27" claim-type="Currently amended] The ketone derivative of the general formula [1D] or a pharmacologically acceptable salt thereof according to claim 1, wherein: In the general formula [1D] above, A D is an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 4 carbon atoms; B D is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 4 carbon atoms; X D is S, O or SO; Y D is an aliphatic hydrocarbon group having 1 to 6 carbon atoms, wherein at least one hydrogen is substituted with a carboxyl group or a group derived therefrom, an amino group or a group derived therefrom, or a hydroxy group or a group derived therefrom; Z D is a carboxyl group or a group derived therefrom, an unsubstituted or substituted alkyl or alkenyl group, a hydroxy group or a group derived therefrom, an amino group or a group derived therefrom, a monocyclic aromatic heterocycle, a halogen having 1 to 4 carbon atoms Or hydrogen. [28" claim-type="Currently amended] The ketone derivative of formula [1D] or a pharmacologically acceptable salt thereof according to claim 27, wherein: In the general formula [1D] above, A D is an aliphatic hydrocarbon group having 1 to 4 carbon atoms; B D is hydrogen or an aliphatic hydrocarbon group having 1 to 4 carbon atoms; X D is S, O or SO; Y D is an aliphatic hydrocarbon group having 1 to 6 carbon atoms (where at least one hydrogen is a carboxyl group, COOR1 (where R1 is a substituted or unsubstituted alkyl or alkenyl group having 1 to 4 carbon atoms), CONR2R3 (where R2 and R3, respectively) May be the same as or different from each other, and each independently hydrogen or an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, COW (where W is a carboxyl group or group derived therefrom or an amino group or group derived therefrom) Ring or substituted heterocyclic ring, NR4R5, wherein R4 and R5 may each be the same or different, and each independently hydrogen, unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or unsubstituted or substituted with 1 to 5 carbon atoms OR 6, where R 6 is hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms Hwandoem shown below); Z D is a carboxyl group, COOR7 (where R7 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), CONR8R9 (where R8 and R9 may be the same or different, respectively, and are each independently hydrogen or 1 to 4 carbon atoms) Unsubstituted or substituted alkyl group, cyano group, CH 2 OR10 (where R10 is hydrogen, unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or unsubstituted or substituted acyl group having 1 to 5 carbon atoms) , Hydroxy group, OCOR11 (where R11 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), NR12R13 (where R12 and R13 may each be the same or different, and are each independently hydrogen, unsubstituted 1 to 4 carbon atoms) Or a substituted alkyl group, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms), 5-tetrazolyl, chlorine, fluorine or hydrogen. [29" claim-type="Currently amended] The ketone derivative of formula [1D] or a pharmacologically acceptable salt thereof according to claim 28, wherein: In the general formula [1D] above, A D is an alkyl group having 1 to 4 carbon atoms; B D is hydrogen or an alkyl group having 1 to 4 carbon atoms; X D is S; Y D is an aliphatic hydrocarbon group of 1 to 6 carbon atoms (where at least two hydrogens are carboxyl groups, COOR1 '(where R1' is an alkyl or alkenyl group of 1 to 4 carbon atoms), NHCOR14 (where R14 is hydrogen fluorine) Optionally substituted with a C1-4 alkyl group), a hydroxy group, or OCOR15, where R15 is a C1-4 alkyl group; Z D is a carboxy group, COOR7 '(where R7' is an alkyl group having 1 to 4 carbon atoms), or CH 2 OR10 '(where R10' is an acyl group having 1 to 5 carbon atoms). [30" claim-type="Currently amended] The ketone derivative of formula [1D] or a pharmacologically acceptable salt thereof according to claim 29, wherein: In the general formula [1D] above, A D is methyl; B D is hydrogen; X D is S; Y D is 2-acetylamino-2-carboxyethyl or 2-acetylamino-2-methoxycarbonylethyl; Z D is carboxyl group, methoxycarbonyl, acetoxymethyl or hydroxymethyl. [31" claim-type="Currently amended] The ketone derivative of the general formula [1D] or a pharmacologically acceptable salt thereof according to claim 1, wherein: In the general formula [1D] above, A D is an unsubstituted or substituted aromatic hydrocarbon, aromatic heterocyclic ring or saturated heterocyclic ring; B D is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 4 carbon atoms; X D is S, O or SO; Y D is an aliphatic hydrocarbon group having 1 to 6 carbon atoms, wherein at least one hydrogen is substituted with a carboxyl group or a group derived therefrom, an amino group or a group derived therefrom or a hydroxy group or a group derived therefrom; Z D is a carboxyl group or group derived therefrom, an unsubstituted or substituted alkyl group or alkenyl group, hydroxy group or group derived therefrom, an amino group or a group derived therefrom, a monocyclic aromatic heterocycle, a halogen having 1 to 4 carbon atoms Or hydrogen. [32" claim-type="Currently amended] 32. The ketone derivative of general formula [1D] or a pharmacologically acceptable salt thereof according to claim 31, wherein: In the general formula [1D] above, A D is an unsubstituted benzene ring, and when substituted, the hydrogen atoms of 1 to 3 are unsubstituted or substituted alkyl groups having 1 to 4 carbon atoms, halogen, hydroxy groups, alkoxy groups having 1 to 4 carbon atoms, amino groups, and carbon atoms 1-4 alkyl- or dialkylamino groups, thiols, carboxy groups, alkoxycarbonyl groups having 1 to 4 carbon atoms, acyloxy groups having 1 to 5 carbon atoms, acylthio groups having 1 to 5 carbon atoms, and 1 to 5 carbon atoms Substituted by an acylamino group, cyano group or trifluoromethyl group; B D is hydrogen or an aliphatic hydrocarbon group having 1 to 4 carbon atoms; X D is S, O or SO; Y D is an aliphatic hydrocarbon group having 1 to 6 carbon atoms (where at least one hydrogen is a carboxyl group, COOR1 (where R1 is a substituted or unsubstituted alkyl or alkenyl group having 1 to 4 carbon atoms), CONR2R3 (where R2 and R3, respectively) May be the same as or different from each other, and each independently hydrogen or an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, COW (where W is a carboxyl group or group derived therefrom or an amino group or group derived therefrom) Ring or a heterocyclic ring which may be substituted), NR4R5 (wherein R4 and R5 may each be the same or different, each independently represent hydrogen, unsubstituted or substituted alkyl or C1-5 unsubstituted or OR 6 (where R 6 is hydrogen, unsubstituted or substituted alkyl group of 1 to 4 carbon atoms or unsubstituted or substituted acyl of 1 to 5 carbon atoms) Group); Z D is a carboxyl group, COOR7 (where R7 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), CONR8R9 (where R8 and R9 may be the same or different, respectively, and are each independently hydrogen or 1 to 4 carbon atoms) Unsubstituted or substituted alkyl group, cyano group, CH 2 OR10 (where R10 is hydrogen, unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or unsubstituted or substituted acyl group having 1 to 5 carbon atoms) , Hydroxy group, OCOR11 (where R11 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), NR12R13 (where R12 and R13 may each be the same or different, and are each independently hydrogen, unsubstituted 1 to 4 carbon atoms) Or a substituted alkyl group, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms), 5-tetrazolyl, chlorine, fluorine or hydrogen. [33" claim-type="Currently amended] 33. The ketone derivative of general formula [1D] or a pharmacologically acceptable salt thereof according to claim 32, wherein: In the general formula [1D] above, A D is an unsubstituted or substituted benzene ring, and when substituted, hydrogen of 1 to 3 is substituted by methyl group, methoxy group, methoxycarbonyl group, nitro group, cyano group, halogen or trifluoromethyl group; B D is hydrogen or an alkyl group having 1 to 4 carbon atoms; X D is S; Y D is an aliphatic hydrocarbon group of 1 to 6 carbon atoms (where at least two hydrogens are carboxyl groups, COOR1 '(where R1' is an alkyl or alkenyl group of 1 to 4 carbon atoms), NHCOR14 (where R14 is hydrogen fluorine) Optionally substituted with a C1-4 alkyl group), a hydroxy group, or OCOR15, where R15 is a C1-4 alkyl group; Z D is a carboxy group, COOR7 '(where R7' is an alkyl group having 1 to 4 carbon atoms), or CH 2 OR10 '(where R10' is an acyl group having 1 to 5 carbon atoms). [34" claim-type="Currently amended] The ketone derivative of formula [1D] or a pharmacologically acceptable salt thereof according to claim 33, wherein: In the general formula [1D] above, A D is an unsubstituted benzene ring or a benzene ring substituted with a methyl group or a methoxy group; B D is hydrogen; X D is S; Y D is 2-acetylamino-2-carboxyethyl, 2-acetylamino-2-methoxycarbonylethyl or 2-acetylaminoethyl; Z D is a carboxy group, methoxycarbonyl group, acetoxymethyl group or hydroxymethyl group. [35" claim-type="Currently amended] The ketone derivative of the general formula [1D] or a pharmacologically acceptable salt thereof according to claim 1, wherein: In the general formula [1D] above, A D and B D are joined together to form an unsubstituted or substituted cycloalkane-1-one ring having 3 to 7 carbon atoms (excluding 5 carbon atoms); X D is S, O or SO; Y D is an aliphatic hydrocarbon group having 1 to 6 carbon atoms, wherein at least one hydrogen is substituted with a carboxyl group or a group derived therefrom, an amino group or a group derived therefrom or a hydroxy group or a group derived therefrom; Z D is a carboxyl group or group derived therefrom, an unsubstituted or substituted alkyl group or alkenyl group, hydroxy group or group derived therefrom, an amino group or a group derived therefrom, a monocyclic aromatic heterocycle, a halogen having 1 to 4 carbon atoms Or hydrogen. [36" claim-type="Currently amended] 36. The ketone derivative of general formula [1D] or a pharmacologically acceptable salt thereof according to claim 35, wherein: In the general formula [1D] above, A D and B D are joined together to form an unsubstituted or substituted cyclobutan-1-one ring or cyclohexan-1-one ring; X D is S, O or SO; Y D is an aliphatic hydrocarbon group having 1 to 6 carbon atoms (where at least one hydrogen is a carboxyl group, COOR1 (where R1 is a substituted or unsubstituted alkyl or alkenyl group having 1 to 4 carbon atoms), CONR2R3 (where R2 and R3, respectively) May be the same as or different from each other, and each independently hydrogen or an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, COW (where W is a carboxyl group or group derived therefrom or an amino group or group derived therefrom) Ring or a heterocyclic ring which may be substituted), NR4R5 (wherein R4 and R5 may each be the same or different, each independently represent hydrogen, unsubstituted or substituted alkyl or C1-5 unsubstituted or OR 6 (where R 6 is hydrogen, unsubstituted or substituted alkyl group of 1 to 4 carbon atoms or unsubstituted or substituted acyl of 1 to 5 carbon atoms) Group); Z D is a carboxyl group, COOR7 (where R7 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), CONR8R9 (where R8 and R9 may be the same or different, respectively, and are each independently hydrogen or 1 to 4 carbon atoms) Unsubstituted or substituted alkyl group, cyano group, CH 2 OR10 (where R10 is hydrogen, unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or unsubstituted or substituted acyl group having 1 to 5 carbon atoms) , Hydroxy group, OCOR11 (where R11 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms), NR12R13 (where R12 and R13 may each be the same or different, and are each independently hydrogen, unsubstituted 1 to 4 carbon atoms) Or a substituted alkyl group, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms), 5-tetrazolyl, chlorine, fluorine or hydrogen. [37" claim-type="Currently amended] The ketone derivative of formula [1D] or a pharmacologically acceptable salt thereof according to claim 36, wherein: In the general formula [1D] above, A D and B D are joined together to form a cyclobutan-1-one ring or a cyclohexan-1-one ring; X D is S; Y D is an aliphatic hydrocarbon group of 1 to 6 carbon atoms (where at least two hydrogens are carboxyl groups, COOR1 '(where R1' is an alkyl or alkenyl group of 1 to 4 carbon atoms), NHCOR14 (where R14 is hydrogen fluorine) Optionally substituted with a C1-4 alkyl group), a hydroxy group, or OCOR15, where R15 is a C1-4 alkyl group; Z D is a carboxy group, COOR7 '(where R7' is an alkyl group having 1 to 4 carbon atoms), or CH 2 OR10 '(where R10' is an acyl group having 1 to 5 carbon atoms). [38" claim-type="Currently amended] The ketone derivative of general formula [1D] or a pharmacologically acceptable salt thereof according to claim 37, wherein: In the general formula [1D] above, (I) A D and B D combine together to form a cyclobutan-1-one ring, X D is S, Y D is 2-acetylamino-2-carboxyethyl, and Z D is a carboxy group; (II) A D and B D join together to form a cyclobutan-1-one ring, X D is S, Y D is 2-acetylamino-2-methoxycarbonyl group ethyl, and Z D is a methoxycarbonyl group ego; (III) A D and B D combine together to form a cyclobutan-1-one ring, X D is S, Y D is 2,3-dihydroxy-n-propyl, and Z D is acetoxymethyl ego; (IV) A D and B D are bonded together to form a cyclobutan-1-one ring, X D is S, Y D is 2-acetylamino-2-carboxyethyl, and Z D is a carboxy group. [39" claim-type="Currently amended] The β-di-substituted aminoketone derivative of the general formula [1F] or a pharmacologically acceptable salt thereof according to claim 1, wherein In the above general formula [1F], A F is an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 4 carbon atoms; B F is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 4 carbon atoms; X F and Y F are linear or branched aliphatic hydrocarbon groups having 1 to 10 carbon atoms, wherein at least one hydrogen is a carboxyl group or a group derived therefrom, an amino group or a group derived therefrom, or a hydroxy group or derived therefrom May be optionally substituted with a group, or X F and Y F are bonded directly to each other or through a hetero atom to form a monocyclic hetero ring (where at least one hydrogen is an alkyl group having 1 to 4 carbon atoms, a phenyl group or a carboxy group) Or may be optionally substituted with a group derived therefrom, an amino group or a group derived therefrom, or a hydroxy group or a group derived therefrom; Z F is a carboxyl group or a group derived therefrom, an unsubstituted or substituted alkyl or alkenyl group, a hydroxy group or a group derived therefrom, an amino group or a group derived therefrom, a monocyclic aromatic heterocycle or a halogen having 1 to 4 carbon atoms to be. [40" claim-type="Currently amended] 40. The β-di-substituted aminoketone derivative of the general formula [1F] or a pharmacologically acceptable salt thereof according to claim 39, wherein: In the above general formula [1F], A F is an unsubstituted or substituted methyl group, ethyl group, n-propyl group or isopropyl group; B F is hydrogen; X F and Y F may be the same as or different from each other, and each independently represent an alkyl group having 1 to 6 carbon atoms, or X F and Y F are bonded directly to each other or through a hetero atom, and have 1 to 4 carbon atoms. A monocyclic hetero ring which may be unsubstituted or substituted with an alkyl group or a phenyl group of; Z F is a carboxy group, COOR1 (where R1 is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a phenyl group), CONR2R3 (where R2 and R3 may be the same or different, respectively, independently hydrogen or carbon atoms 1 to 4 represents an unsubstituted or substituted alkyl group, a cyano group, CH 2 OR4 (wherein R4 is hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms) Hydroxy group, OR5 (where R5 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms), NR6R7 (where R6 and R7 are each the same or May be different from each other and independently represent hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms), 5-tetrazolyl, chlorine or fluorine. [41" claim-type="Currently amended] 41. The β-di-substituted aminoketone derivative of the general formula [1F] or a pharmacologically acceptable salt thereof according to claim 40, wherein: In the above general formula [1F], A F is a methyl group; B F is hydrogen; X F and Y F are both ethyl, n-propyl or isopropyl groups, and X F and Y F are bonded directly to each other or through a hetero atom to form pyrrolidine, piperidine, morpholine, 4-methylpipe To form a lazine or 4-phenylpiperazine ring; Z F is a carboxy group, COOR1 '(where R1' is an alkyl group having 1 to 4 carbon atoms), CONR2'R3 '(where R2' and R3 'may be the same or different and are each hydrogen or an alkyl group having 1 to 4 carbon atoms) ) Or cyano group. [42" claim-type="Currently amended] The β-di-substituted aminoketone derivative of the general formula [1F] or a pharmacologically acceptable salt thereof according to claim 1, wherein In the above general formula [1F], A F is an unsubstituted or substituted aryl group, heteroaryl group, or saturated heterocycle; B F is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 4 carbon atoms; X F and Y F are linear or branched aliphatic hydrocarbon groups having 1 to 10 carbon atoms, wherein at least one hydrogen is a carboxyl group or a group derived therefrom, an amino group or a group derived therefrom, or a hydroxy group or derived therefrom May be optionally substituted with a group) or X F and Y F are bonded directly to each other or through a hetero atom to form a hetero ring (where at least one hydrogen is an alkyl group having 1 to 4 carbon atoms, a phenyl group, a carboxyl group or from Optionally substituted with a derived group, an amino group or a group derived therefrom, or a hydroxy group or a group derived therefrom); Z F is a carboxyl group or a group derived therefrom, an unsubstituted or substituted alkyl or alkenyl group, a hydroxy group or a group derived therefrom, an amino group or a group derived therefrom, a monocyclic aromatic heterocycle or a halogen having 1 to 4 carbon atoms to be. [43" claim-type="Currently amended] 43. The β-di-substituted aminoketone derivative of the general formula [1F] or a pharmacologically acceptable salt thereof according to claim 42, wherein: In the above general formula [1F], A F is an unsubstituted or substituted benzene ring or a monocyclic aromatic heterocyclic heterocycle; B F is hydrogen; X F and Y F may be the same or different and are a straight or branched aliphatic hydrocarbon group having 1 to 6 carbon atoms, or X F and Y F are bonded directly to each other or through a hetero atom, and have 1 to 1 carbon atoms. To form a substituted or unsubstituted heterocyclic alkyl group or phenyl group of 4; Z F is a carboxy group, COOR1 (where R1 is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a phenyl group), CONR2R3 (where R2 and R3 may be the same or different, respectively, independently hydrogen or carbon atoms 1 to 4 represents an unsubstituted or substituted alkyl group, a cyano group, CH 2 OR4 (wherein R4 is hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms) Hydroxy group, OR5 (where R5 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms), NR6R7 (where R6 and R7 are each the same or May be different from each other and independently represent hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms), 5-tetrazolyl, chlorine or fluorine. [44" claim-type="Currently amended] The β-di-substituted aminoketone derivative of the general formula [1F] or a pharmacologically acceptable salt thereof according to claim 43, wherein: In the above general formula [1F], A F is an unsubstituted or substituted benzene ring, and when substituted, a hydrogen atom of 1 to 3 is an alkyl group having 1 to 4 carbon atoms, a halogen, a hydroxyl group, an alkoxy group having 1 to 4 carbon atoms, an amino group or a carbon atom having 1 to 3 carbon atoms. 4 alkyl- or dialkylamino groups, thiols, carboxyl groups, alkoxycarbonyl groups having 1 to 4 carbon atoms, acyloxy groups having 1 to 5 carbon atoms, acylthio groups having 1 to 5 carbon atoms, and acylamino groups having 1 to 5 carbon atoms Substituted by a cyano group or a trifluoromethyl group; B F is hydrogen; X F and Y F are good even if each the same or different, or alkyl groups of carbon atoms 1 to 6, or X F is and Y F are directly bonded to each other or bonded through a hetero atom to the carbon atom alkyl group or a phenyl group of atoms from 1 to 4 To form a substituted or unsubstituted heterocycle; Z F is a carboxy group, COOR1 '(where R1' is an alkyl group having 1 to 4 carbon atoms), CONR2'R3 '(where R2' and R3 'may be the same or different, respectively, hydrogen or each of 1 to 4 carbon atoms). An alkyl group), a cyano group, and CH 2 OR4 '(where R4' is hydrogen, an alkyl group having 1 to 4 carbon atoms or an acyl group having 1 to 5 carbon atoms). [45" claim-type="Currently amended] 45. The β-di-substituted aminoketone derivative of the general formula [1F] or a pharmacologically acceptable salt thereof according to claim 44, wherein: In the above general formula [1F], A F is an unsubstituted or substituted benzene ring, in which, when substituted, one to three hydrogen atoms are substituted with a methyl group, a methoxy group, a methoxycarbonyl group, a nitro group, a cyano group, a halogen or a trifluoromethyl group; B F is hydrogen; X F and Y F are both ethyl groups, n-propyl groups, or isopropyl groups, or X F and Y F are directly bonded to each other or through a hetero atom to form pyrrolidine, piperidine, morpholine, 4 -Form methylpiperazine or 4-phenylpiperazine ring; Z F is a carboxy group, COOR1 '' (where R1 '' is a methyl group or ethyl group), CONR2''R3 '' (where R2 '' and R3 '' may be the same or different and are each hydrogen, methyl or ethyl group) Or cyano group. [46" claim-type="Currently amended] The β-di-substituted aminoketone derivative of the general formula [1F] or a pharmacologically acceptable salt thereof according to claim 1, defined as follows: In the above general formula [1F], A F and B F are bonded together to form an unsubstituted or substituted cycloalkane-1-one ring having 3 to 7 carbon atoms, or A F and B F are bonded together to form a carbon atom fused with an aromatic hydrocarbon or aromatic heterocycle. A cycloalkane-1-one ring of embroidery 3 to 7 is formed; X F and Y F are linear or branched aliphatic hydrocarbon groups having 1 to 10 carbon atoms, wherein at least one hydrogen is a carboxyl group or a group derived therefrom, an amino group or a group derived therefrom, or a hydroxy group or derived therefrom May be optionally substituted with a group, or X F and Y F are bonded directly to each other or through a hetero atom to form a hetero ring (where at least one hydrogen is an alkyl group having 1 to 4 carbon atoms, a phenyl group, a carboxyl group or Optionally substituted with a group derived from, an amino group or a group derived therefrom, or a hydroxy group or a group derived therefrom); Z F is a carboxyl group or a group derived therefrom, an unsubstituted or substituted alkyl or alkenyl group, a hydroxy group or a group derived therefrom, an amino group or a group derived therefrom, a monocyclic aromatic heterocycle or a halogen having 1 to 4 carbon atoms to be. [47" claim-type="Currently amended] 47. The β-di-substituted aminoketone derivative of the general formula [1F] or a pharmacologically acceptable salt thereof according to claim 46, wherein: In the above general formula [1F], A F and B F are bonded together to form an unsubstituted or substituted cycloalkane-1-one ring having 4 to 6 carbon atoms, or an unsubstituted 4 to 6 carbon atoms fused with an aromatic hydrocarbon or a monocyclic aromatic heterocycle, or To form a substituted cycloalkane-1-one ring; Each of X F and Y F may be the same or different and independently represents a linear or branched aliphatic hydrocarbon group having 1 to 6 carbon atoms, or X F and Y F are directly bonded to each other or through a hetero atom To form a monocyclic heterocyclic ring (which may be unsubstituted or substituted with an alkyl group having 1 to 4 carbon atoms or a phenyl group); Z F is a carboxy group, COOR1 (where R1 is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a phenyl group), CONR2R3 (where R2 and R3 may be the same or different, respectively, independently hydrogen or carbon atoms 1 to 4 represents an unsubstituted or substituted alkyl group, a cyano group, CH 2 OR4 (wherein R4 is hydrogen, an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms) Hydroxy group, OR5 (where R5 is an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, or an unsubstituted or substituted acyl group having 1 to 5 carbon atoms, preferably an alkyl group having 1 to 4 carbon atoms or NR6R7 (where each of R6 and R7 may be the same or different, and are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or an acyl group having 1 to 5 carbon atoms), 5-tetrazolyl, Chlorine or fluorine. [48" claim-type="Currently amended] The β-di-substituted aminoketone derivative of the general formula [1F] or a pharmacologically acceptable salt thereof according to claim 47, wherein: In the above general formula [1F], A F and B F combine together to form an unsubstituted or substituted cyclobutan-1-one ring, or an unsubstituted or substituted cyclopentan-1-one ring fused with benzene or a monocyclic aromatic heterocycle; Each of X F and Y F may be the same or different and independently represents an alkyl group having 1 to 6 carbon atoms, or X F and Y F are each directly bonded to each other or through a hetero atom to form an alkyl group having 1 to 4 carbon atoms. Or a monocyclic hetero ring which may be unsubstituted or substituted with a phenyl group; Z F is a carboxy group, COOR1 '(where R1' is an alkyl group having 1 to 4 carbon atoms), CONR2'R3 '(where R2' and R3 'may be the same or different, respectively, hydrogen or carbon atoms having 1 to 4 atoms, respectively An alkyl group), a cyano group, or CH 2 OR4 '(where R4' is hydrogen, an alkyl group having 1 to 4 carbon atoms or an acyl group having 1 to 5 carbon atoms). [49" claim-type="Currently amended] The β-di-substituted aminoketone derivative of the general formula [1F] according to claim 48 or a pharmacologically acceptable salt thereof: In the above general formula [1F], A F and B F join together to form a cyclobutan-1-one ring or indan-1-one ring; X F and Y F are both ethyl, n-propyl, or isopropyl groups, or X F and Y F are bonded directly to each other or through a hetero atom to form pyrrolidine, piperidine, morpholine, 4 -Form methylpiperazine or 4-phenylpiperazine ring; Z F is a carboxy group, COOR1 '' (where R1 '' is a methyl or ethyl group), CONR2''R3 '' (where R2 '' and R3 '' may be the same or different and are each hydrogen, methyl or ethyl group) Or cyano group. [50" claim-type="Currently amended] The cyclopentanone derivative of the general formula [1A] or the cyclopentanone derivative according to any one of claims 2 to 6, which further includes the definitions of the following (1) to (7). Or a pharmacologically acceptable salt thereof as an active ingredient: (1) when Z1 A and Z2 A are hydrogen, X A is S, Y A is a methyl group or benzyl group, Z3 A is a methoxycarbonyl group, (2) when Z1 A and Z2 A are hydrogen, X A is O or N, Y A is a benzyl group, Z3 A is a carboxy group, methoxycarbonyl group or ethoxycarbonyl group, (3) X A is N or O, Z 1 A and Z 3 A are hydrogen, Z 2 A is a carboxy group, methoxycarbonyl group, (4) X A is O, Z 1 A is a hydroxyl group or a group derived therefrom, Z 2 A is a hydrogen, Z 3 A is an amino group or a group derived therefrom, (5) X A is S, Y1 A is a phenyl group, Z1 A is a dimethoxymethyl group, Z2 A and Z3 A are hydrogen, (6) X A is O, Y 1 A is a methyl group, Z 1 A is a 1-methoxy-1-phenylthiomethyl group, Z 2 A and Z 3 A are hydrogen, (7) Z 1 A is S, SO or SO 2 , Z 2 A is a hydroxy group or a group derived therefrom, Z 3 A is hydrogen. [51" claim-type="Currently amended] The cyclopentanone derivative of the general formula [1A] or the cyclopentanone derivative according to any one of claims 2 to 6, which further includes the definitions of the following (1) to (7). Or a pharmacologically acceptable salt thereof as an active ingredient, a composition for treating central nervous system disorders: (1) when Z1 A and Z2 A are hydrogen, X A is S, Y A is a methyl group or benzyl group, Z3 A is a methoxycarbonyl group, (2) when Z1 A and Z2 A are hydrogen, X A is O or N, Y A is a benzyl group, Z3 A is a carboxy group, methoxycarbonyl group or ethoxycarbonyl group, (3) X A is N or O, Z 1 A and Z 3 A are hydrogen, Z 2 A is a carboxy group, methoxycarbonyl group, (4) X A is O, Z 1 A is a hydroxyl group or a group derived therefrom, Z 2 A is a hydrogen, Z 3 A is an amino group or a group derived therefrom, (5) X A is S, Y1 A is a phenyl group, Z1 A is a dimethoxymethyl group, Z2 A and Z3 A are hydrogen, (6) X A is O, Y 1 A is a methyl group, Z 1 A is a 1-methoxy-1-phenylthiomethyl group, Z 2 A and Z 3 A are hydrogen, (7) Z 1 A is S, SO or SO 2 , Z 2 A is a hydroxy group or a group derived therefrom, Z 3 A is hydrogen. [52" claim-type="Currently amended] The cyclopentanone derivative of the general formula [1A] or the cyclopentanone derivative according to any one of claims 2 to 6, which further includes the definitions of the following (1) to (7). Or a pharmacologically acceptable salt thereof as an active ingredient, a composition for treating peripheral neuropathy: (1) when Z1 A and Z2 A are hydrogen, X A is S, Y A is a methyl group or benzyl group, Z3 A is a methoxycarbonyl group, (2) when Z1 A and Z2 A are hydrogen, X A is O or N, Y A is a benzyl group, Z3 A is a carboxy group, methoxycarbonyl group or ethoxycarbonyl group, (3) X A is N or O, Z 1 A and Z 3 A are hydrogen, Z 2 A is a carboxy group, methoxycarbonyl group, (4) X A is O, Z 1 A is a hydroxyl group or a group derived therefrom, Z 2 A is a hydrogen, Z 3 A is an amino group or a group derived therefrom, (5) X A is S, Y1 A is a phenyl group, Z1 A is a dimethoxymethyl group, Z2 A and Z3 A are hydrogen, (6) X A is O, Y 1 A is a methyl group, Z 1 A is a 1-methoxy-1-phenylthiomethyl group, Z 2 A and Z 3 A are hydrogen, (7) Z 1 A is S, SO or SO 2 , Z 2 A is a hydroxy group or a group derived therefrom, Z 3 A is hydrogen. [53" claim-type="Currently amended] The cyclopentanone derivative of the general formula [1A] or the cyclopentanone derivative according to any one of claims 2 to 6, which further includes the definitions of the following (1) to (7). Or a pharmacologically acceptable salt thereof as an active ingredient, a composition for promoting neuronal differentiation: (1) when Z1 A and Z2 A are hydrogen, X A is S, Y A is a methyl group or benzyl group, Z3 A is a methoxycarbonyl group, (2) when Z1 A and Z2 A are hydrogen, X A is O or N, Y A is a benzyl group, Z3 A is a carboxy group, methoxycarbonyl group or ethoxycarbonyl group, (3) X A is N or O, Z 1 A and Z 3 A are hydrogen, Z 2 A is a carboxy group, methoxycarbonyl group, (4) X A is O, Z 1 A is a hydroxyl group or a group derived therefrom, Z 2 A is a hydrogen, Z 3 A is an amino group or a group derived therefrom, (5) X A is S, Y1 A is a phenyl group, Z1 A is a dimethoxymethyl group, Z2 A and Z3 A are hydrogen, (6) X A is O, Y 1 A is a methyl group, Z 1 A is a 1-methoxy-1-phenylthiomethyl group, Z 2 A and Z 3 A are hydrogen, (7) Z 1 A is S, SO or SO 2 , Z 2 A is a hydroxy group or a group derived therefrom, Z 3 A is hydrogen. [54" claim-type="Currently amended] 2,3-di-substituted cyclopentanone derivatives of the general formula [1B] or 2,3-di-substituted cyclopentanone derivatives according to any one of claims 7 to 18, or pharmacologically acceptable Pharmaceutical composition containing a salt as an active ingredient. [55" claim-type="Currently amended] 2,3-di-substituted cyclopentanone derivatives of the general formula [1B] or 2,3-di-substituted cyclopentanone derivatives according to any one of claims 7 to 18, or pharmacologically acceptable A composition for the treatment of central nervous system disorder containing a salt as an active ingredient. [56" claim-type="Currently amended] 2,3-di-substituted cyclopentanone derivatives of the general formula [1B] or 2,3-di-substituted cyclopentanone derivatives according to any one of claims 7 to 18, or pharmacologically acceptable A composition for the treatment of peripheral nerve disorders containing the salt thereof as an active ingredient. [57" claim-type="Currently amended] 2,3-di-substituted cyclopentanone derivatives of the general formula [1B] or 2,3-di-substituted cyclopentanone derivatives according to any one of claims 7 to 18, or pharmacologically acceptable A composition for promoting neuronal differentiation comprising a salt as an active ingredient. [58" claim-type="Currently amended] A cyclopentanone derivative of the general formula [1C] or a cyclopentanone derivative according to any one of claims 19 to 26, or a pharmacologically acceptable salt thereof, wherein when X C is O or NH, Z 1 C And Z 3 C is hydrogen, and Z 2 C further comprises hydrogen or a hydroxyl group or a group derived therefrom, wherein the cyclopentanone derivative is contained as an active ingredient. [59" claim-type="Currently amended] A cyclopentanone derivative of the general formula [1C] or a cyclopentanone derivative according to any one of claims 19 to 26, or a pharmacologically acceptable salt thereof, wherein when X C is O or NH, Z 1 C And Z 3 C is hydrogen, and Z 2 C further comprises hydrogen or a hydroxyl group or a group derived therefrom, wherein the cyclopentanone derivative is contained as an active ingredient. [60" claim-type="Currently amended] A cyclopentanone derivative of the general formula [1C] or a cyclopentanone derivative according to any one of claims 19 to 26, or a pharmacologically acceptable salt thereof, wherein when X C is O or NH, Z 1 C And Z 3 C is hydrogen, and Z 2 C further comprises hydrogen or a hydroxyl group or a group derived therefrom, wherein the cyclopentanone derivative is contained as an active ingredient. [61" claim-type="Currently amended] A cyclopentanone derivative of the general formula [1C] or a cyclopentanone derivative according to any one of claims 19 to 26, or a pharmacologically acceptable salt thereof, wherein when X C is O or NH, Z 1 C And Z 3 C is hydrogen, and Z 2 C further comprises hydrogen or a hydroxyl group or a group derived therefrom, wherein the cyclopentanone derivative is contained as an active ingredient. [62" claim-type="Currently amended] A ketone derivative of the general formula [1D] according to claim 1 or a ketone derivative according to any one of claims 26 to 38, or pharmacologically, further including the definitions of (1) to (4) below. Pharmaceutical composition containing the salt as an active ingredient which is acceptable as: When A D and B D are bonded together to form a cyclobutane ring, the ketone derivative is (1) X D is O, Y D is a methyl group, n-octyl group or n-hexadecyl group, and Z D is a methoxycarbonyl group; (2) X D is O, Y D is a benzyl group, and Z D is a benzyloxymethyl group; (3) X D is O, Y D is p-methoxybenzyl group, and Z D is p-methoxybenzyloxymethyl group; (4) When X D is O, Y D is a trityl group, Z D is a trityloxymethyl group, and A D is an unsubstituted benzene ring and B D is hydrogen, X D is S, Y D is a methyl group, an ethyl group Or isopropyl group and Z D is a carboxy group. [63" claim-type="Currently amended] A ketone derivative of the general formula [1D] according to claim 1 or a ketone derivative according to any one of claims 26 to 38, or pharmacologically, further including the definitions of (1) to (4) below. A composition for the treatment of central neuropathy, containing the salt thereof as an active ingredient, which is acceptable as: When A D and B D are bonded together to form a cyclobutane ring, the ketone derivative is (1) X D is O, Y D is a methyl group, n-octyl group or n-hexadecyl group, and Z D is a methoxycarbonyl group; (2) X D is O, Y D is a benzyl group, and Z D is a benzyloxymethyl group; (3) X D is O, Y D is p-methoxybenzyl group, and Z D is p-methoxybenzyloxymethyl group; (4) When X D is O, Y D is a trityl group, Z D is a trityloxymethyl group, and A D is an unsubstituted benzene ring and B D is hydrogen, X D is S, Y D is a methyl group, an ethyl group Or isopropyl group and Z D is a carboxy group. [64" claim-type="Currently amended] A ketone derivative of the general formula [1D] according to claim 1 or a ketone derivative according to any one of claims 26 to 38, or pharmacologically, further including the definitions of (1) to (4) below. A composition for the treatment of peripheral neuropathy, containing the salt thereof as an active ingredient, which is acceptable as: When A D and B D are bonded together to form a cyclobutane ring, the ketone derivative is (1) X D is O, Y D is a methyl group, n-octyl group or n-hexadecyl group, and Z D is a methoxycarbonyl group; (2) X D is O, Y D is a benzyl group, and Z D is a benzyloxymethyl group; (3) X D is O, Y D is p-methoxybenzyl group, and Z D is p-methoxybenzyloxymethyl group; (4) When X D is O, Y D is a trityl group, Z D is a trityloxymethyl group, and A D is an unsubstituted benzene ring and B D is hydrogen, X D is S, Y D is a methyl group, an ethyl group Or isopropyl group and Z D is a carboxy group. [65" claim-type="Currently amended] A ketone derivative of the general formula [1D] according to claim 1 or a ketone derivative according to any one of claims 26 to 38, or pharmacologically, further including the definitions of (1) to (4) below. A composition for promoting neuronal differentiation, the salt of which is acceptable as an active ingredient: When A D and B D are bonded together to form a cyclobutane ring, the ketone derivative is (1) X D is O, Y D is a methyl group, n-octyl group or n-hexadecyl group, and Z D is a methoxycarbonyl group; (2) X D is O, Y D is a benzyl group, and Z D is a benzyloxymethyl group; (3) X D is O, Y D is p-methoxybenzyl group, and Z D is p-methoxybenzyloxymethyl group; (4) When X D is O, Y D is a trityl group, Z D is a trityloxymethyl group, and A D is an unsubstituted benzene ring and B D is hydrogen, X D is S, Y D is a methyl group, an ethyl group Or isopropyl group and Z D is a carboxy group. [66" claim-type="Currently amended] A pharmaceutical composition containing a compound of the general formula [1E] or a pharmacologically acceptable salt thereof as an active ingredient. [67" claim-type="Currently amended] A composition for the treatment of central nervous system, which contains a compound of the general formula [1E] or a pharmacologically acceptable salt thereof as an active ingredient. [68" claim-type="Currently amended] A composition for the treatment of peripheral nerve disorders containing a compound of the general formula [1E] or a pharmacologically acceptable salt thereof as an active ingredient. [69" claim-type="Currently amended] A composition for promoting neuronal differentiation containing a compound of formula [1E] or a pharmacologically acceptable salt thereof as an active ingredient. [70" claim-type="Currently amended] A β-di-substituted aminoketone derivative of the general formula [1F] or a β-di-substituted aminoketone derivative according to any one of claims 39 to 49, or a pharmacologically acceptable salt thereof, wherein A F is In the case of an unsubstituted benzene ring, the β-di-substituted aminoketone derivatives further include those wherein B F is hydrogen, X F is directly bonded to Y F to form a piperidine ring, and Z F is a carboxy group. A pharmaceutical composition comprising the β-di-substituted aminoketone derivative or a pharmacologically acceptable salt thereof as an active ingredient. [71" claim-type="Currently amended] A β-di-substituted aminoketone derivative of the general formula [1F] or a β-di-substituted aminoketone derivative according to any one of claims 39 to 49, or a pharmacologically acceptable salt thereof, wherein A F is In the case of an unsubstituted benzene ring, the β-di-substituted aminoketone derivatives further include those wherein B F is hydrogen, X F is directly bonded to Y F to form a piperidine ring, and Z F is a carboxy group. A composition for treating central nervous system disorder, comprising the β-di-substituted aminoketone derivative or a pharmacologically acceptable salt thereof as an active ingredient. [72" claim-type="Currently amended] As the β-di-substituted aminoketone derivative of the general formula [1F] or the β-di-substituted aminoketone derivative according to any one of Claims 39 to 49, or a pharmacologically acceptable salt thereof, A When F is an unsubstituted benzene ring, the β-di-substituted aminoketone derivatives further include those in which B F is hydrogen, X F is directly bonded to Y F to form a piperidine ring, and Z F is a carboxyl group. To, wherein the β-di-substituted amino ketone derivative or a pharmacologically acceptable composition containing the salt as an active ingredient for the treatment of peripheral neuropathy. [73" claim-type="Currently amended] A β-di-substituted aminoketone derivative of the general formula [1F] or a β-di-substituted aminoketone derivative according to any one of claims 39 to 49, or a pharmacologically acceptable salt thereof, wherein A F is In the case of an unsubstituted benzene ring, the β-di-substituted aminoketone derivatives further include those wherein B F is hydrogen, X F is directly bonded to Y F to form a piperidine ring, and Z F is a carboxy group. A composition for promoting neuronal differentiation comprising the β-di-substituted aminoketone derivative or a pharmacologically acceptable salt thereof as an active ingredient.
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同族专利:
公开号 | 公开日 US6384063B1|2002-05-07| CA2297943A1|1999-02-04| EP0999204A1|2000-05-10| CN1268937A|2000-10-04| ES2226156T3|2005-03-16| AU8357898A|1999-02-16| EP0999204A4|2001-10-04| WO1999005091A1|1999-02-04| AU740782B2|2001-11-15| DE69827006T2|2005-02-24| PL338242A1|2000-10-09| BR9811486A|2000-09-19| DE69827006D1|2004-11-18| AT279387T|2004-10-15| EP0999204B1|2004-10-13|
引用文献:
公开号 | 申请日 | 公开日 | 申请人 | 专利标题
法律状态:
1997-07-25|Priority to JP21389697 1997-07-25|Priority to JP97-213896 1997-07-30|Priority to JP21837097 1997-07-30|Priority to JP9218371A 1997-07-30|Priority to JP21837297 1997-07-30|Priority to JP97-218372 1997-07-30|Priority to JP97-218371 1997-07-30|Priority to JP97-218370 1997-08-29|Priority to JP97-247534 1997-08-29|Priority to JP24753497 1998-01-16|Priority to JP98-18305 1998-01-16|Priority to JP1830498 1998-01-16|Priority to JP10018306A 1998-01-16|Priority to JP1830598 1998-01-16|Priority to JP98-18304 1998-01-16|Priority to JP98-18306 1998-01-16|Priority to JP1830798 1998-01-16|Priority to JP98-18307 1998-07-24|Application filed by 닛뽄카야쿠가부시키가이샤 1998-07-24|Priority to PCT/JP1998/003313 2001-03-15|Publication of KR20010022204A
优先权:
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申请号 | 申请日 | 专利标题 JP21389697|1997-07-25| JP97-213896|1997-07-25| JP9218371A|JPH1149718A|1997-07-30|1997-07-30|New cyclopentanone derivative and its use| JP21837297|1997-07-30| JP97-218372|1997-07-30| JP21837097|1997-07-30| JP97-218371|1997-07-30| JP97-218370|1997-07-30| JP24753497|1997-08-29| JP97-247534|1997-08-29| JP1830498|1998-01-16| JP10018306A|JPH11100344A|1997-07-30|1998-01-16|New 2,3-disubstituted cyclopentanone derivative and its use| JP1830598|1998-01-16| JP98-18304|1998-01-16| JP98-18306|1998-01-16| JP1830798|1998-01-16| JP98-18307|1998-01-16| JP98-18305|1998-01-16| PCT/JP1998/003313|WO1999005091A1|1997-07-25|1998-07-24|Novel compound having effect of promoting neuron differentiation| 相关专利
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