 1,2-diaryl benzimidazoles for treating illnesses associated with a microglia activation
专利摘要:
The present invention relates to 1,2-diarylbenzimidazoles of formula I and the use of benzimidazole derivatives for the preparation of pharmaceutical preparations for use in the treatment and prevention of diseases associated with microglial activation. 公开号:KR20020063629A 申请号:KR1020027009085 申请日:2001-01-12 公开日:2002-08-03 发明作者:요아킴 쿤케；볼프강 할프브로드트；우르술라 모엔니히 申请人:쉐링 악티엔게젤샤프트； IPC主号:
专利说明:
1,2-DIARYL BENZIMIDAZOLES FOR TREATING ILLNESSES ASSOCIATED WITH A MICROGLIA ACTIVATION FOR THE TREATMENT OF DISEASES CONCERNING MICROSCOPIC ACTIVITY [1] The present invention relates to novel benzimidazole derivatives and the use of benzimidazole derivatives for the preparation of pharmaceutical preparations for the prevention and treatment of diseases associated with microglial activation. [2] Nearly all degenerative diseases of the central nervous system are associated with chronic inflammation. The central stage of the inflammation process is the activation of monocyte cells, which are microcytes. This occurs, for example, in Alzheimer's disease by the elderly, by Creutzfeldt-Jacob disease by Prion protein, and by ischemic stroke by dead cells. Microglial cells can be maintained for extended periods of time in an active state that produces and secretes a variety of inflammatory factors, such as reactive oxygen / nitrogen intermediates, proteolytic enzymes, cytokines, complement factors, and neurotoxins. The latter leads to neuropathy and neurodegeneration. [3] For the possible treatment of neuroinflammation, up to now non-steroidal anti-inflammatory drugs (COX II inhibitors) (McGeer, PL; Roger, Neurology 42, 447-449 (1992), Rogers, J. et al. ; Kirby, LC; Hempleman, SR; Berry, DL; McGeer, PL; Kaszniak, AW; Zalinski, Cofield, M .; Mansukhani, L .; Wilson, P., Kogan, F. Neurology 43, 1609-1611 (1993), Andersen, K .; Launer, LJ, Ott, A .; Hoes, AW, Breteler, MMB; Hofman, A. Neurology 45, 1441-1445 (1995), Breitner JCS; Gau; BA; Welsh; KA; Plassman; BL; McDonald, WM; Helms, MJ; Anthony, JC Neurology 44, 227-232 (1994), The Canadian Study of Health and Aging, Neurology 44, 2073-2079 (1994)), cytokine modulators (McGeer, PL; McGeer, EG Brain Res. Rev 21: 195-218 (1995), McGeer, EG McGeer, PL, CNS Drugs 7, 214-228 (1997), Barone ), FC and Pfuerstein, GZ, J. Cerebral Blood Flow and Metabolism 19, 819-834 (1999)) and complement inhibitors (Chen. Frederickson, R. C. A., and Brunden, K. R., Neurobiol. Aging (1996), McGeer, E. G .; McGeer, P. L., Drugs 55: 739-746 (1998)). These substances inhibit the synthesis or action of individual inflammatory factors. However, it would be desirable to have a substance that inhibits the development or action of many inflammatory factors by inhibiting the early stages of the inflammatory process. [4] This problem has been solved by the preparation of benzimidazole derivatives of formula (I), their tautomers or isomers or salts. [5] [6] here, [7] R 1 is a monocyclic or bicyclic C 6-12 aryl group or a monocyclic or bicyclic 5- to 10-membered heteroaryl group having 1 to 4 heteroatoms selected from the group consisting of N, S, or O (The above-mentioned aryl or heteroaryl groups may be substituted independently of each other by not more than 3 of the following substituents: [8] F, Cl, Br, I, C (NH) NH 2, C (NH) NHR 4, C (NH) NR 4 R 4 ', C (NR 4) NH 2, C (NR 4) NHR 4', C (NR 4) NR 4 R 4 ', XOH, XOR 4, XOCOR 4, XOCONHR 4, XOCOOR 4, XCOR 4, XC (NOH) R 4, XC (NOR 4) R 4', XC (NO (COR 4) ) R 4 ', XCN, XCOOH , XCOOR 4, XCONH 2, XCONR 4 R 4', XCONHR 4, XCONHOH, XCONHOR 4, XCOSR 4, XSR 4, XSOR 4, XSO 2 R 4, S0 2 NH 2, S0 2 NHR 4, SO 2 NR 4 R 4 ', N0 2, XNH 2, XNHR 4, XNR 4 R 4', XNHS0 2 R 4, XN (SO 2 R 4) SO 2 R 4 ', XNR 4 SO 2 R 4 ', XNHCOR 4, XNHCOOR 4, XNHCONHR 4, tetrahydro-2,5-dioxide Sophie roll-yl, 2,5-dihydro-2,5-dioxide Sophie roll-yl, 2,7-di 2,7-dioxoisoindol-1-yl, R 4 , wherein the two substituents of R 1 , if they are in ortho position with respect to one another, together are methane diyl bisoxy, ethane-1,2-diylbisoxy , Propane-1,3-diyl, butane-1,4-diyl)), [9] R 2 is a monocyclic or bicyclic C 6-10 aryl group or a monocyclic or bicyclic 5- to 10-membered heteroaryl having 1 to 4 heteroatoms selected from the group consisting of N, S or O group (the above-mentioned aryl or heteroaryl groups, independently of each other, may be substituted with substituent to three: F, Cl, Br, I, XOH, XOR 4, XOCOR 4, XOCONHR 4, XOCOOR 4, XCOR 4 , XC (NOH) R 4, XC (NOR 4) R 4 ', XC (NO (COR 4)) R 4', XCOOH, XCOOR 4, XCONH 2, XCONHR 4, XCONR 4 R 4 ', XCONHOH, XCONHOR 4 , XCOSR 4, XSR 4, XSOR 4, XSO 2 R 4, SO 2 NH 2, S0 2 NHR 4, SO 2 NR 4 R 4 ', N0 2, XNHR 4, XNR 4 R 4', XNHSO 2 R 4, XN (SO 2 R 4) SO 2 R 4 ', XNR 4 SO 2 R 4', tetrahydro-2,5-dioxide Sophie roll-yl, 2,5-dihydro-2,5-dioxide Sophie roll 1-yl, 2,7-dihydro-2,7-dioxo-isoindol If the 1-yl, R 4 (wherein, if the two substituents to each other ortho position of R 2, they together methane di Bis-oxy, ethane-1,2-diyl-bis-oxy, it means that can be connected to each other in such a manner as to form a propan-1,3-diyl, butane-1,4-diyl)), and [10] R 3 is hydrogen, F, Cl, Br, I, XOH, XOR 4 , XOCOR 4 , XOCONHR 4 , XOCOOR 4 , [11] XCOR 4, XC (NOH) R 4, XC (NOR 4) R 4 ', XC (NO (COR 4)) R 4', XCN, XCOOH, XCOOR 4, XCONH 2, XCONHR 4, XCONR 4 R 4 ', XCONHOH, XCONHOR 4, XCOSR 4, XSR 4, XSOR 4, XSO 2 R 4, SO 2 NH 2, S0 2 NHR 4, S0 2 NR 4 R 4 ', N0 2, XNH 2, XNHR 4, XNR 4 R 4 ', XNHSO 2 R 4, XNR 4 SO 2 R 4', XN (SO 2 R 4) (SO 2 R 4 '), XNHCOR 4, XNHCOOR 4, XNHCONHR 4, tetrahydro-2,5-dioxide Sophie roll- Dihydro-2,5-dioxopyrrol-1-yl, 2,7-dihydro-2,7-dioxoisoindol-1-yl, or one or two Or R 3 may denote R 4 , wherein two substituents R 3 , if they are in ortho position with respect to one another, may together denote methandiylbisoxy, ethane-1,2-diylbisoxy, propane -1, 3-diyl, or butane-1,4-diyl, [12] R 4 and R 4 'are independently C 1-4 perfluoroalkyl, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, (C 1- each other 3 alkyl-C 3-7 cycloalkyl), C 1-3 alkyl-C 6-10 aryl, C 1-3 alkyl- (5-10 membered heteroaryl containing 1-4 N, S, or O atoms), C 6-10 aryl or 5 to 10 membered heteroaryl containing 1 to 4 N, S or 0 atoms wherein the aryl and heteroaryl groups are optionally substituted with F, Cl, Br, CH 3 , C 2 H 5 , NO 2 , OCH 3 , OC 2 H 5 , CF 3 .C 2 F 5 , or may be substituted by one or two substituents selected from the group consisting of an annelated methanediylbisoxy group or ethane- And one ring atom in the 5-membered cycloalkyl ring may be N or 0, and one or two ring atoms in the 6- or 7-membered cycloalkyl ring may be substituted by N and / or O And the ring nitrogen may optionally be substituted with C < 1 > 3 alkyl or C 1-3 alkanoyl)), [13] R 5 and R 5 ' independently of one another are selected from the group consisting of C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl wherein one carbon atom is O, S, SO, SO 2 , NH, NC 1- 3 alkyl or NC 1-3 alkanoyl), C 3-7 cycloalkyl - C 0-3 alkyl wherein one ring atom of the 5 membered cycloalkyl ring may be N or 0, and 6 Or one or two ring atoms of the 7-membered cycloalkyl ring may be N and / or O, and the ring nitrogen may be optionally substituted with C 1-3 alkyl or C 1-3 alkanoyl), C 6 -10 aryl, or 5-10 membered heteroaryl containing 1 to 4 N, S or O heteroatoms wherein said alkyl, alkenyl and alkynyl chains are optionally substituted with one or more of the above-mentioned cycloalkyl, aryl or heteroaryl And all the above-mentioned alkyl and cycloalkyl radicals may be substituted by one of CF 3 , C 2 F 5 , OH, OC 1-3 alkyl, NH 2 , NHC 1-3 alkyl, NHC 1-3 alkanoyl, N (C 1-3 alkyl) 2 , N (C 1-3 alkyl) (C 1-3 alkanoyl), COOH, CONH 2 , COOC 1-3 alkyl, and all aryl and heteroaryl groups F, Cl, Br, CH 3 , C 2 H 5, N0 2, OCH 3, OC 2 H 5, CF 3, and may be substituted either by one or two substituents of the group from consisting of C 2 F 5, Or may be accompanied by an annelated methanediylbisoxy or ethane-1,2-diylbisoxy group, [14] Or R 5 and R 5 'can contain, one more oxygen, nitrogen or sulfur atom together with the N atom and C 1-4 alkyl, C 1-4 alkoxy -C 2 O-alkyl, C 1-4 alkoxy- Form a 5- to 7-membered heterocyclic compound which may be substituted with carbonyl, aminocarbonyl or phenyl, [15] A is C 1-10 alkanediyl, C 2-10 Al canned yl, C 2-10 alkyne diyl, (C O-5 alkanediyl -C 3-7 cycloalkyl alkanediyl -C 0-5 alkanediyl ) Wherein one ring atom of the five membered cycloalkyl ring may be N or O, one or two ring atoms of the 6 or 7 membered cycloalkyl ring may be N and / or O, and ring nitrogen may be Optionally substituted with C 1-3 alkyl or C 1-3 alkanoyl; one or two carbon atoms of the above-mentioned aliphatic chain may be replaced by 0, NH, NC 1-3 alkyl, NC 1-3 alkanoyl It can be and; alkyl or cycloalkyl group = O, OH, OC 1-3 alkyl, NH 2, NHC 1-3 alkyl, NHC 1-3 alkanoyl, N (C 1-3 alkyl) 2, N (C 1 -3 alkyl) (C < RTI ID = 0.0 > 1-3 < / RTI > alkanoyl) [16] B is selected from the group consisting of COOH, COOR 5 , CONH 2 , CONHNH 2 , CONHR 5 , CONR 5 R 5 ' , CONHOH, CONHOR 5 , SO 3 H, SO 2 NH 2 , SO 2 NHR 5 , SO 2 NR 5 R 5' 3 H, PO (OH) ( OR 5), PO (OR 5) (OR 5 '), PO (OH) (NHR 5), PO (NHR 5) (NHR 5' means), tetrazolyl, and (each Lt; RTI ID = 0.0 > A < / RTI > [17] Or the whole group YAB means a N (SO 2 R 4) ( SO 2 R 4 ') or NHSO 2 R 4, [18] X is a bond, CH 2, (CH 2) 2, CH (CH 3), (CH 2) 3, CH (CH 2 CH 3), CH (CH 3) CH 2, CH 2 means CH (CH 3) and, [19] Y represents O, NH, NR 4 , NCOR 4 , NSO 2 R 4 , [20] With the proviso that when Y represents NH, NR 4 , NCOR 4 or NSO 2 R 4 , [21] a) In addition, provided that the substituent R < 2 > comprises a saturated heterocyclic compound containing nitrogen, the heterocyclic compound is not substituted by hydrogen, methyl, ethyl, propyl or isopropyl in the imine nitrogen, [22] b) a substituent "in R 4 and (or) R 4 'groups XNHR 4 or XNR 4 R 4, which optionally present in R 2 does not mean a C 1-4 alkyl, [23] Wherein the latter are independently of one another unsubstituted or substituted by one or more substituents selected from the group consisting of C 1-6 alkyl, C 1-4 perfluoroalkyl, OC 1-6 alkyl, OC 1-4 perfluoroalkyl, COOH, COOC 1-6 alkyl , COC 1-6 alkyl, CONH 2 , CONHR 4 , NO 2 , NH 2 , NHCOR 4 , NHSO 2 R 4 or by one or two halogen atoms from the group consisting of F, Cl, Br and I, , B does not simultaneously mean COOH, SO 3 H, PO 3 H 2 or tetrazolyl, R 1 and R 2 independently of one another denote C 5-6 heteroaryl or phenyl, [24] Here, the following compounds are excluded: [25] [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] acetic acid methyl ester, [26] 5 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] pentanoic acid methyl ester, [27] 4 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] butanoic acid ethyl ester, [28] 5 - [[1- (4-nitrophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] pentanoic acid methyl ester, [29] 6 - [[1- (4-nitrophenyl) -2- phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [30] 5 - [[1- (4-aminophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] pentanoic acid methyl ester, [31] Amino] phenyl] -2-phenyl-1H-benzimidazol-6-yl] oxy] pentanoic acid methyl ester, [32] Phenyl] -1H-benzimidazol-6-yl] oxy] pentanoic acid methyl ester, [33] 5 - [[1- (3-nitrophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] pentanoic acid methyl ester, [34] 6 - [[1- (3-nitrophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [35] 5 - [[1- (3-aminophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] pentanoic acid methyl ester, [36] Amino] phenyl] -2-phenyl-1H-benzimidazol-6-yl] oxy] pentanoic acid methyl ester, 5- [ [37] 5 - [[1- [3 - [(acetyl) amino] phenyl] -2-phenyl-1H-benzimidazol-6-yl] oxy] pentanoic acid methyl ester. [38] Salts that are physiologically compatible may be formed with inorganic and organic acids such as, for example, oxalic, lactic, citric, fumaric, acetic, maleic, tartaric, phosphoric, HCl, HBr, sulfuric, p-toluenesulfonic and methanesulfonic acids have. [39] For the acid salt formation, for example, alkali hydroxides such as sodium and potassium hydroxide, alkaline earth hydroxides such as calcium hydroxide, ammonia, ethanolamine, diethanolamine, triethanolamine, N-methylglue Also suitable are inorganic or organic bases known for the formation of physiologically compatible salts such as amines such as carmine, tris- (hydroxymethyl) -methylamine. [40] &Quot; Aryl group " is especially defined as an optionally substituted phenyl group or biphenyl, naphthyl, indan or fluorenyl. [41] The heteroaryl group consists of 5-10 skeletal atoms and may contain 1-4 heteroatoms. Hetero atoms are oxygen (0), nitrogen (N), and sulfur (S). Examples of monocyclic heteroaryl groups include pyrrolyl, thienyl, furanyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyrazolyl, furanyl, pyridyl, pyrimidinyl, Lt; / RTI > and pyridazinyl. Examples of bicyclylheteroaryl groups include thienoimidazolyl, indolyl, isoindolyl, benzothiophenyl, benzofuranyl, benzimidazolyl, indazolyl, imidazopyridinyl, pyridinyl, quinolyl, iso Quinolyl, phthalazinyl, quinazolinyl, quinacolonyl, cinnolinyl, naphthyridinyl and phthiridinyl. If the aryl or heteroaryl group is part of R < 1 & gt ;, the bond of the benzimidazole to N is through the carbon atom. [42] The alkyl group may be linear or branched. For example, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n- pentyl, sec-pentyl, tert- pentyl, neopentyl, Octyl, nonyl and hexyl. [43] The perfluorinated alkyl is preferably CF 3 and C 2 F 5 , and the alkanoyl is preferably formyl, acetyl and propionyl. [44] The alkenyl group may be straight-chain or branched. Examples of the radicals include the following radicals: vinyl, 2-propenyl, 1-propenyl, 2-butenyl, 1-butenyl, 1-methyl- Phenyl, 3-methyl-2-propenyl. [45] The alkynyl group may be straight-chain or branched. Examples of these are ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, and 2-butynyl. [46] Each cycloalkyl group is defined as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl. [47] As the saturated heterocyclic compound or the cycloalkyl having at least one hetero atom, for example, piperidine, pyrrolidine, tetrahydrofuran, morpholine, piperazine, hexahydroazepine, as well as 2,6-dimethylmorpholine , N-phenylpiperazine, methoxymethylpyrrolidine (wherein the bond with the carbon adjacent to the ring may be made by optionally present ring nitrogen) can be mentioned. [48] Alkenes, alkenes and alkynes of A include, for example, straight or branched chain alkylene having 1-8 C atoms such as methylene, ethylene, propylene, butylene, pentylene, 1-methylethylene, 1 -Ethylethylene, 1-methylpropylene, 2-methylpropylene, 1-methylbutylene, 2-methylbutylene, 1-ethylbutylene, 2-ethylbutylene, 1-methylpentylene, 3-methylpentylene, and the like can be mentioned. [49] Straight or branched alkenylene and alkynylene having 2 to 8 C atoms are alkenylene or alkynylene groups having double and triple bonds at all possible positions as well as all possible methyl or ethyl substituents. Among these radicals, in each case one or two C atoms may be replaced by 0, NH, NC 1-3 alkyl or NC 1-3 alkanoyl, wherein the substituted group is separated from Y by two or more C atoms . [50] If the two radicals are in the ortho position, they may form a common ring with adjacent aromatic compounds. If, for example, such bonds are not clearly defined in the heteroaromatic compounds or functional groups mentioned in the claims, compounds in which N, O or S atoms are bonded to olefinic or acetylic multiple bonds or some N, O, S Or a compound in which a halogen atom is bonded to the same aliphatic carbon atom or a compound in which N, O or S atoms are directly bonded to each other is excluded. [51] R 1 is a monocyclic or bicyclic C 6-12 aryl group or a monocyclic or bicyclic 5- to 10-membered heteroaryl group having 1 to 2 heteroatoms selected from the group consisting of N, S or O (the above mentioned aryl or heteroaryl groups, independently of each other, may be substituted with substituent to three: F, Cl, Br, XOH, XOR 4, XOCOR 4, XOCONHR 4, XOCOOR 4, XCOR 4, XCN, XCOOH, XCOOR 4, XCONH 2, XCONR 4 R 4 ', XCONHR 4, XCONHOH, XCONHOR 4, XCOSR 4, XSR 4, NO 2, XNHR 4, XNR 4 R 4', R 4 ( wherein, in R 1 two If the substituents are in the ortho position to each other, they may be linked together in such a way that they form together methane diyl bisoxy, ethane-1,2-diyl bisoxy, propane-1,3-diyl or butane-1,4-diyl )) Is preferred. [52] R 2 is monocyclic or bicyclic C 6-10 aryl group or monocyclic or bicyclic 5 to 10 membered heteroatom having 1 to 2 heteroatoms selected from the group consisting of N, S or 0, aryl group (the above-mentioned aryl or heteroaryl groups, independently of each other, may be substituted with substituent to three: F, Cl, Br, XOH, XOR 4, XOCOR 4, XOCONHR 4, XOCOOR 4, XCOR 4, XC (NOH) R 4, XC (NOR 4) R 4 ', XC (NO (COR 4)) R 4', XCOOH, XCOOR 4, XCONH 2, XCONHR 4, XCONR 4 R 4 ', XCONHOH, XCONHOR 4, XCOSR 4, XSR 4, XSOR 4 , XSO 2 R 4, SO 2 NH 2, S0 2 NHR 4, SO 2 NR 4 R 4 ', N0 2, XNHR 4, XNR 4 R 4', XNHSO 2 R 4, XN (SO 2 R 4 ) SO 2 R 4 ' , XNR 4 SO 2 R 4' , R 4 wherein the two substituents of R 2 , if they are in ortho position with respect to one another, together with methandiylbisoxy, 2-diyl bisoxy, propane-1,3-diyl, butane-1,4-diyl. The benzimidazole, which means negative)) are preferred. [53] In addition, R 3 are, independently of each other, hydrogen, F, Cl, Br, XOH , XOR 4, XOCOR 4, XOCONHR 4, XOCOOR 4, XCOR 4, XC (NOH) R 4, XC (NOR 4) R 4 ', XC (NO (COR 4)) R 4 ', XCN, XSR 4, XSOR 4, XSO 2 R 4, SO 2 NH 2, S0 2 NHR 4, S0 2 NR 4 R 4', N0 2, XNH 2, XNHR 4 , XNR 4 R 4 ' , XNHSO 2 R 4 , XNR 4 SO 2 R 4' , XN (SO 2 R 4 ) (SO 2 R 4 ' ), XNHCOR 4 , XNHCOOR 4 , XNHCONHR 4 or R 4 One or two substituents wherein two substituents R < 3 > are taken together if they are in ortho position to each other, they together form a saturated or unsaturated, Benzylidene, benzimidazole, benzimidazole, benzimidazole, and the like. [54] R 4 and R 4 ' are independently of each other CF 3 , C 2 F 5 , C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 3-6 cycloalkyl, (C 1 -3 alkyl, -C 3-6 cycloalkyl), phenyl, or 1 to 2 N, S or 0, a 5 to 6 membered heteroaryl group containing atoms (wherein the phenyl and heteroaryl groups F, Cl, Br, CH 3, C 2 H 5 , OCH 3 , OC 2 H 5 , CF 3 and C 2 F 5 ; furthermore, one ring atom of the five membered cycloalkyl ring may be substituted by 1 or 2 substituents selected from the group consisting of N Or 0 and one or two ring atoms of the six-membered cycloalkyl ring may be N and / or O, and the ring nitrogen may be optionally substituted with C 1-3 alkyl or C 1-3 alkanoyl. Benzimidazole of the formula (I) < / RTI > [55] In addition, R 5 and R 5 'are independently C 1-6 alkyl (wherein one carbon atom The 0, NH, NC 1-3 alkyl, or may be replaced by a NC 1-3 alkanoyl) or C 3- each other 7 cycloalkyl, -C 3 O-alkyl (wherein 1 ring atoms of 5-membered cycloalkyl ring, or N may be 0, 6, or 7-membered cycloalkyl ring in one or two ring atoms are N, and (or) 0, and the ring nitrogen may be optionally substituted with C 1-3 alkyl or C 1-3 alkanoyl, and the above-mentioned C 1-6 alkyl moiety may be substituted with one of the above-mentioned cycloalkyls or N, S or 5 to 6 membered heteroaryl may be substituted by an aromatic compound, all the alkyl and cycloalkyl portions referred to above having from 1 to 2 heteroatoms selected from O, from CF 3, OH, OC 1-3 alkyl group consisting of 2 may be substituted with a substituent of one or less, the above-mentioned heteroaryl groups F, Cl, CF 3, CH 3, C 2 H 5, OCH 3 , OC < 2 > H < 5 >), or alternatively, [56] Or R 5 and R 5 'can contain, one more oxygen, nitrogen or sulfur atom together with the N atom and C 1-4 alkyl, C 1-4 alkoxy -C 2 O-alkyl, C 1-4 alkoxy- Or a 5- to 7-membered heterocyclic compound which may be substituted with a carbonyl, an aminocarbonyl or a phenyl. [57] A is selected from the group consisting of C 1-10 alkanediyl, C 2-10 alkenediyl, C 2-10 alkynediyl, or (C 5 -5 alkanediyl - C 3-7 cycloalkanediyl-C 0-5 Wherein one ring atom of the five membered cycloalkyl ring may be N or O, one or two ring atoms of the 6 or 7 membered cycloalkyl ring may be N and / or O, The ring nitrogen may be optionally substituted with C 1-3 alkyl or C 1-3 alkanoyl; one or two carbon atoms of the above-mentioned aliphatic chain may be replaced by O, NH, NC 1-3 alkyl, NC 1-3 alkaryl Benzylimidazole < / RTI & [58] B is benzimidazole of the formula I which means COOH, COOR 5 , CONH 2 , CONHR 5 , CONR 5 R 5 ' , CONHOH, CONHOR 5 or tetrazolyl, in each case bound to the carbon atom of the group A Dissol is preferred. [59] Particularly preferred when B is COOR 5 , CONH 2 , CONHR 5 , CONR 5 or R 5 . [60] Also preferred are benzimidazoles of the formula I in which X signifies a bond or methylene. [61] Also preferred are benzimidazoles of formula (I) wherein Y signifies O. [62] In particular, R 1 and R 2 are each independently phenyl or N, O, or 5 to 6 membered heteroaryl group (which is F, Cl, Br, cyano, C 1-4 alkyl, a hetero atom such as S atoms having 1 to 2 , C 1-4 alkoxy, methylenedioxy, C 1-4 alkylthio, NO 2, CF 3, NH 2, NH (C 1-3 alkyl), N (C 1-3 alkyl) may be substituted with 2 ). [63] R 3 is H, F, Cl, OH, C 1-4 - alkoxy, C 1-4 - alkyl, NO 2, NH 2, NH -C 1-4 - alkanoyl, NH-SO 2 - or Benzyl-NH- Particular preference is given to SO 2 -phenyl, wherein the phenyl radical may be substituted by F, Cl, Br, C 1-4 alkyl, C 1-4 -alkoxy, CF 3 or acetylamino. [64] The following benzimidazoles are particularly preferred: [65] [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] acetic acid isopropyl ester, [66] 3 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] propanoic acid methyl ester, [67] 2 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] propanoic acid methyl ester, [68] 4 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] butanoic acid isopropyl ester, [69] 5 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] pentanoic acid isopropyl ester, [70] 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid methyl ester, [71] 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid isopropyl ester, [72] 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide, [73] Methoxy-6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide, [74] N- (phenylmethoxy) -6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide, [75] N-hydroxy-6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide, [76] 7 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] heptanoic acid methyl ester, [77] 6 - [[1- (3-nitrophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, [78] 6 - [[2-phenyl-1- [3- (trifluoromethyl) phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [79] 6 - [[2-phenyl-1- [3- (trifluoromethyl) phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, [80] 6 - [[1- (3-cyanophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [81] 6 - [[1- (3-cyanophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, [82] 6 - [[1- (3-cyanophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid, [83] 6 - [[1- (4-cyanophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [84] 6 - [[1- (4-cyanophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, [85] 6 - [[1- (3-chlorophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [86] 6 - [[1- (3-chlorophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, [87] 6 - [[1- (4-chlorophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [88] 6 - [[1- (4-chlorophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, [89] 6 - [[1- (3-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [90] 6 - [[1- (3-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, [91] 6 - [[1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [92] 6 - [[1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, [93] 6 - [[1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [94] 6 - [[1- (3,5-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [95] 6 - [[1- (3,5-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, [96] 6 - [[1- (3-methoxyphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [97] 6 - [[1- (4-methoxyphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [98] 6 - [[1- (3,4-dimethoxyphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [99] 6 - [[1- [3,4- (methylenedioxy) phenyl] -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [100] 6 - [[1- [3,4- (methylenedioxy) phenyl] -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid, [101] 6 - [[2-phenyl-1- (3,4,5-trimethoxyphenyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [102] 6 - [[2-phenyl-1- (3,4,5-trimethoxyphenyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid, [103] 6 - [[2-phenyl-1- (3,4,5-trimethoxyphenyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, [104] Phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [105] Phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid, < [106] 6 - [[1-phenyl-2- [3- (trifluoromethyl) phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, [107] 6 - [[2- (3-chlorophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [108] 6 - [[2- (3-chlorophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, [109] 6 - [[2- (4-chlorophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [110] 6 - [[2- (4-chlorophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, [111] 6 - [[2- (4-methylphenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [112] 6 - [[2- (4-methylphenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, [113] 6 - [[1-phenyl-2- (4-pyridinyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [114] 6 - [(1,2-diphenyl-5-nitro-1H-benzimidazol-6-yl) oxy] hexanoic acid methyl ester, [115] 6 - [(1,2-diphenyl-5-nitro-1H-benzimidazol-6-yl) oxy] hexanoic acid isopropyl ester, [116] Amino] -1,2-diphenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, [117] Amino] -1,2-diphenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [118] Amino] -1,2-diphenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, [119] 6 - [[1,2-diphenyl-5 - [[(3-methylphenyl) sulfonyl] amino] -1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, [120] 6 - [[1,2-diphenyl-5 - [(4-methylphenyl) sulfonyl] amino] -1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, [121] Amino] -1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, 6 - [[ [122] Phenyl] sulfonyl] amino] -1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, [123] Amino] -1,2-diphenyl-1H-benzimidazol-6-yl] oxy] -hexanoic acid isopropyl ester, [124] Amino] -1,2-diphenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, [125] 6 - [[1,2-diphenyl-5 - [(propylsulfonyl) amino] -1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, [126] 6 - [[5 - [(benzylsulfonyl) amino] -1,2-diphenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, [127] 2 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] ethoxy] acetic acid methyl ester, [128] 3- [2 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] ethoxy] -propanoic acid methyl ester, [129] 6 - [[1- (3-nitrophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid ethyl ester, [130] 6 - [[4-acetyl-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [131] 6 - [[1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-5-yl] oxy] hexanoic acid methyl ester, [132] Phenyl] -1H-benzimidazol-5-yl] oxy] hexanoic acid methyl ester, [133] 6 - [[2-phenyl-1 - [(4- (thiomethyl) phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [134] 6 - [[2-phenyl-1- (3-thienyl) -1H-benzimidazol-5-yl] oxy] hexanoic acid methyl ester, [135] 6 - [[2-phenyl-1- (3-thienyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [136] 4 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] butanoic acid methyl ester, [137] Phenyl] -1H-benzimidazol-6-yl] oxy] -hexanamide, N- (phenylmethoxy) -6- [ [138] N, N-dimethyl-6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide, [139] N-isopropyl-6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide, [140] 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] -1- pyrrolidin- 1 -yl-hexan- [141] Amino] -1,2-diphenyl-1H-benzimidazol-6-yl] oxy] pentanoic acid methyl ester, [142] Methyl] -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [143] (4-methoxyphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester , [144] 6 - [[4- (acetyloxy) -1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [145] 6 - [[4-hydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [146] 6 - [[4-hydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid, [147] 6 - [[7-methyl-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [148] 6 - [[2-phenyl-1- (3-pyridyl) -1H-benzimidazol-5-yl] oxy] hexanoic acid methyl ester, [149] 6 - [[2-phenyl-1- (3-pyridyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [150] 6 - [[2-phenyl-1- (4-pyridyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [151] 6 - [[2- (4-fluoro-phenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [152] 6 - [[2- (4-methoxyphenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [153] 6 - [[2- (4-bromophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [154] 6 - [[2- [4- (trifluoromethyl) phenyl] -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [155] 6 - [[1-phenyl-2- (benzothiene-2-yl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [156] 6 - [[1-phenyl-2- (benzothiene-2-yl) -1H-benzimidazol-6-yl] oxy] hexanoic acid, [157] 6 - [[5-hydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, [158] 6 - [[5-hydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid, [159] 6 - [[5-methoxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, [160] 6 - [[5-hydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [161] 6 - [[5-methoxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [162] Amino] -1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoate Ester benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [163] (4-methoxy-phenyl) -lH-benzimidazol-6-yl < / RTI > ] Oxy] hexanoic acid methyl ester, [164] (4-methoxyphenyl) -1H-benzimidazol-6-yl] -6- [ Oxy] hexanoic acid methyl ester, [165] (4-methoxyphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] butanoic acid methyl ester , [166] 2-phenyl-1H-benzimidazol-6-yl] oxy] pentanoic acid methyl ester , [167] Amino] -1,2-diphenyl-1H-benzimidazol-6-yl] oxy] pentanoic acid methyl ester, [168] (4-methoxyphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy ] Hexanoic acid methyl ester, [169] Methyl] amino] -1- (4-methoxyphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoate ester, [170] 6 - [[1- (indan-5-yl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [171] 6 - [[1- (indan-5-yl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid, [172] 6 - [[1- (3-fluorophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [173] 6 - [[2- (4-nitrophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [174] 6 - [[1-phenyl-2- (3-pyridinyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [175] N- (cyclopropylmethoxy) -6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide, [176] N-isobutoxy-6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide, [177] Phenyl] -1- (3,4,5-trimethoxy-phenyl) -1H-benzimidazol-6-yl) oxy] hexanamide, N- (cyclopropylmethoxy) [178] N-isobutoxy-6- [2-phenyl-1- (3,4,5-trimethoxyphenyl) -1H-benzimidazol-6-yl) oxy] hexanamide, [179] N- (2-methoxyethyl) -6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide, [180] N- (3-methoxy-propyl) -6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide, [181] N-isobutyl-6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide, [182] 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] -1- [183] N, N-di (2-methoxyethyl) -6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide, [184] N-isopentyl-6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide, [185] 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide, N- [186] 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide, N- [187] N-isopropyl-6- [[1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanamide, [188] N, N-dimethyl-6- [[1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanamide, [189] N, N-diethyl-6- [[1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanamide, [190] N-isobutyl-6 - [[1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanamide, [191] N-cyclopropyl-6 - [[1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanamide, [192] N-cyclobutyl-6 - [[1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanamide, [193] N-tert-butyl-6- [[1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanamide, [194] 6-yl] oxy] l- (2-methoxymethyl) -pyrrolidin-l- -Hexan-1-one, [195] (3-imidazol-1-yl-propyl) -6 - [[l- (3,4-dimethylphenyl) -2-phenyl-lH-benzimidazol-6-yl] oxy] hexanamide, [196] 2-ylethyl) -6 - [[1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanamide, [197] 6-yl] oxy] heptane amide, N- (3-methoxy-propyl) -6 - [[1- (indan- [198] (3-pyridyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [199] 6 - [[1- (4-methylphenyl) -2- (4-pyridyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [200] 6 - [[1- (4-methylphenyl) -2- (2-thienyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [201] 6 - [[1- (4-methylphenyl) -2- (3-thienyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [202] 6 - [[2- (3-indolyl) -1- (4-methylphenyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [203] 6 - [[1- (4-methylphenyl) -2- (2-furyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [204] 6 - [[1- (4-methylphenyl) -2- (3-furyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, [205] 6-yl] oxy] hexanoic acid methyl ester, 6 - [[1- (4-methylphenyl) -2- [206] 6 - [[1- (4-methylphenyl) -2- (3-methyl-2-thienyl) -1H-benzimidazol- 6-yl] oxy] hexanoic acid methyl ester. [207] The benzimidazole derivatives according to the present invention can be used for the production of pharmaceutical preparations for the prevention or treatment of diseases associated with microglia and inhibiting the activity of microglia. Microscopic cells are defined in this application as macrophages of the brain. [208] This action has been shown so far that benzimidazole derivatives have been used only in the treatment of thrombosis and atherosclerosis (EP 0531883, PCT WO 98/07263, EP 0104727, PCT W 097/12613), cystitis (U.S. Patent No. 5,552,426) and treatment of diseases associated with increased Ca-channel activation (European Patent No. EP 520200), and the effect on microglia Is surprising because it was not known. [209] The present invention also relates to the use of benzimidazole of formula II for the preparation of pharmaceutical preparations for the prevention or treatment of diseases associated with microglial activation. [210] [211] (here, [212] R 1 is a monocyclic or bicyclic C 6-12 aryl group or a monocyclic or bicyclic 5- to 10-membered heteroaryl group having 1 to 4 heteroatoms selected from the group consisting of N, S, or O (the above mentioned aryl or heteroaryl groups, independently of each other, may be substituted with substituent to three: F, Cl, Br, I, C (NH) NH 2, C (NH) NHR 4, C (NH ) NR 4 R 4 ', C (NR 4) NH 2, C (NR 4) NHR 4', C (NR 4) NR 4 R 4 ', XOH, XOR 4, XOCOR 4, XOCONHR 4, XOCOOR 4, XOCR 4, XC (NOH) R 4 , XC (NOR 4) R 4 ', XC (NO (COR 4)) R 4', XCN, XCOOH, XCOOR 4, XCONH 2, XCONR 4 R 4 ', XCONHR 4, XCONHOH , XCONHOR 4, XCOSR 4, XSR 4, XSOR 4, XSO 2 R 4, S0 2 NH 2, S0 2 NHR 4, SO 2 NR 4 R 4 ', N0 2, XNH 2, XNHR 4, XNR 4 R 4' , XNHS0 2 R 4, XN ( SO 2 R 4) SO 2 R 4 ', XNR 4 SO 2 R 4', XNHCOR 4, XNHCOOR 4, XNHCONHR 4, tetrahydro-2,5-dioxide Sophie roll-yl , 2,5-dihydro-2,5-dioxopyrrol-1-yl, 2,7-dihydro-2,7-dioxane Isoindol-1-yl, R 4 (where the two substituents of R 1 each other if there at the ortho position, they together methane diyl bis oxy, ethane-1,2-diyl-bis-oxy, propane-1,3-diyl , Butane-1,4-diyl)), [213] R 2 is a monocyclic or bicyclic C 6-10 aryl group or a monocyclic or bicyclic 5- to 10-membered heteroaryl having 1 to 4 heteroatoms selected from the group consisting of N, S or O (Wherein the aryl or heteroaryl groups mentioned above may be substituted independently of each other by up to three substituents: F, Cl, Br, I, C (NH) NH 2 , C (NH) NHR 4 , C NH) NR 4 R 4 ', C (NR 4) NH 2, C (NR 4) NHR 4', C (NR 4) NR 4 R 4 ', XOH, XOR 4, XOCOR 4, XOCONHR 4, XOCOOR 4, XCOR 4, XC (NOH) R 4, XC (NOR 4) R 4 ', XC (NO (COR 4)) R 4', XCN, XCOOH, XCOOR 4, XCONH 2, XCONR 4 R 4 ', XCONHR 4, XCONHOH, XCONHOR 4, XCOSR 4, XSR 4, XSOR 4, XSO 2 R 4, SO 2 NH 2, S0 2 NHR 4, SO 2 NR 4 R 4 ', N0 2, XNH 2, XNHR 4, XNR 4 R 4 ', XNHSO 2 R 4, XN (SO 2 R 4) (SO 2 R 4'), XNR 4 SO 2 R 4 ', XNHCOR 4, XNHCOOR 4, XNHCONHR 4, tetrahydro-2,5-dioxide Sophie roll- Yl, 2,5-dihydro-2,5-dioxopyrrol-1-yl, 2,7-dihydro-2,7-di Soy stamp stone-1-yl, R 4 (wherein the two substituents on R 2, if one another, if in the ortho position, they methane diyl bis oxy, ethane-1,2-diyl-bis oxy together, propane-1,3- Diyl, butane-1,4-diyl)), [214] R 3 are each independently hydrogen, F, Cl, Br, I , XOH, XOR 4, XOCOR 4, XOCONHR 4, XOCOOR 4, XCOR 4, XC (NOH) R 4, XC (NOR 4) R 4 ', XC (NO (COR 4 )) R 4 ' , XCN, XCOOH, XCOOR 4 , XCONH 2 , XCONHR 4 , XCONR 4 R 4' , XCONHOH, XCONHOR 4 , XCOSR 4 , XSR 4 , XSOR 4 , XSO 2 R 4 , SO 2 NH 2, S0 2 NHR 4 , S0 2 NR 4 R 4 ', N0 2, XNH 2, XNHR 4, XNR 4 R 4', XNHSO 2 R 4, XNR 4 SO 2 R 4 ', XN (SO 2 R 4) (SO 2 R 4 ' ), XNHCOR 4, XNHCOOR 4, XNHCONHR 4, tetrahydro-2,5-dioxide Sophie roll-yl, 2,5-dihydro-2,5-dioxide Sophie roll -1 -, 2,7-dihydro-2,7-dioxoisoindol-1-yl or one or two substituents which form R 4 , wherein two substituents R 3 , if they are in an ortho position to each other , Which together may be linked together in such a way as to form methane di bisoxy, ethane-1,2-diybisoxy, propane-1,3-diyl, butane-1,4-diyl) [215] R 4 and R 4 'are independently C 1-4 perfluoroalkyl, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, (C 1- each other 3 alkyl-C 3-7 cycloalkyl), C 1-3 alkyl-C 6-10 aryl, C 1-3 alkyl- (5-10 membered heteroaryl containing 1-4 N, S or O atoms), C 6-10 aryl or 5 to 10 membered heteroaryl containing 1 to 4 N, S or O atoms, wherein the C 6-10 aryl and heteroaryl groups are optionally substituted with F, Cl, Br, CH 3 , C 2 H 5 , . N0 2, OCH 3, OC 2 H 5, CF 3 C 2 F 5 , or may be substituted by one or two substituents from the group consisting of, or ahnel rate (annelate) methane diyl bis oxy group or ethane- One of the ring atoms in the 5-membered cycloalkyl ring may be N or 0, and one or two ring atoms in the 6- or 7-membered cycloalkyl ring may be substituted by N and < RTI ID = 0.0 > (Or) 0, and the ring nitrogen is optional Means a C 1-3 which may be substituted by alkyl or C 1-3 alkanoyl), a, and [216] R 5 and R 5 ' independently of one another are selected from the group consisting of C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl wherein one carbon atom is O, S, SO, SO 2 , NH, NC 1- 3 alkyl or NC 1-3 alkanoyl), C 3-7 cycloalkyl - C 0-3 alkyl wherein one ring atom of the 5 membered cycloalkyl ring may be N or 0, and 6 Or one or two ring atoms in the 7-membered cycloalkyl ring may be N and / or O, and the ring nitrogen may be optionally substituted with C 1-3 alkyl or C 1-3 alkanoyl), C 6 -10 aryl, or 5-10 membered heteroaryl containing 1 to 4 N, S, or 0 heteroatoms, wherein all of the above-mentioned alkyl, alkenyl and alkynyl chains are optionally substituted with one or more of the above-mentioned cycloalkyl, and one of the aryl may be substituted, all the alkyl and cycloalkyl radicals mentioned above is CF 3, C 2 F 5, OH, OC 1-3 alkyl, NH 2, NHC 1-3 alkyl, NHC 1-3 alkanoyl, N (C 3 alkyl) 2 , N (C 1-3 alkyl) (C 1-3 alkanoyl), COOH, CONH 2 , COOC 1-3 alkyl, aryl, and heteroaryl groups with one or two substituents from F, Cl, Br, CH 3 , C 2 H 5, N0 2, OCH 3, OC 2 H 5, CF 3, and the group consisting of C 2 F 5 Which may be substituted or may be accompanied by an annelated methanediylbisoxy or ethane-1,2-diylbisoxy group, [217] Or R 5 and R 5 'can contain, one more oxygen, nitrogen or sulfur atom together with the N atom and C 1-4 alkyl, C 1-4 alkoxy -C 2 O-alkyl, C 1-4 alkoxy- Form a 5- to 7-membered heterocyclic compound which may be substituted with carbonyl, aminocarbonyl or phenyl, [218] A is C 1-10 alkanediyl, C 2-10 Al canned yl, C 2-10 alkyne diyl, (C O-5 alkanediyl -C 3-7 cycloalkyl alkanediyl -C 0-5 alkanediyl ), (C 0-5 alkanediyl arylene -C 0-5 alkanediyl), (C 0-5 alkanediyl-heteroarylene -C 0-5 alkanediyl), (wherein aryl and heteroaryl groups F, Cl, Br, CH 3 , C 2 H 5, NO 2, OCH 3, OC 2 H 5, CF 3, optionally substituted with one or two substituents of the group from consisting of C 2 F 5, and; 5 One of the ring atoms in the first cycloalkyl ring may be N or O, one or two ring atoms in the 6- or 7-membered cycloalkyl ring may be N and / or O, the ring nitrogen may optionally be substituted with C 1-3 Alkyl or C 1-3 alkanoyl; one or two carbon atoms of the above-mentioned aliphatic chain may be replaced by O, NH, NR 4 , NCOR 4 , NSO 2 R 4 ; alkyl or cycloalkyl Is selected from the group consisting of F, OH, OR 4 , OCOR 4 , ═O, NH 2 , NR 4 R 4 ' , NHCOR 4 , NHCOOR 4 , NHCONHR 4 , NHSO 2 R Means 4 SH, it may be substituted) by two substituents or fewer from the group consisting of SR 4, and [219] B is hydrogen, OH, OCOR 5, OCONHR 5 , OCOOR 5 ', COR 5, C (NOH) R 5, C (NOR 5) R 5', C (NO (COR 5)) R 5 ', COOH, COOR 5, CONH 2, CONHNH 2, CONHR 5, CONR 5 R 5 ', CONHOH, CONHOR 5, SO 3 H, S0 2 NH 2, S0 2 NHR 5, SO 2 NR 5 R 5', P0 3 H, PO ( OH) (OR 5), PO (OR 5) (OR 5 '), PO (OH) (NHR 5), PO (NHR 5) (NHR 5' means), tetrazolyl, and (in each case, the a group Or the whole YAB group means N (SO 2 R 4 ) (SO 2 R 4 ' ) or NHSO 2 R 4 , [220] Also X represents a bond, CH 2, (CH 2) 2, CH (CH 3), (CH 2) 3, CH (CHCH 3), CH (CH 3) CH 2, CH 2 CH (CH 3), [221] Y represents a bond, O, S, SO, SO 2 , NH, NR 4 , NCOR 4 , NSO 2 R 4 , [222] In addition to the novel compounds of formula (I), the compounds of formula (II) also include known compounds (EP 0531883, DE 4330959). According to the present invention, the compound of formula (II) inhibits the activation of microglial cells. This action is also novel in the case of known compounds. [223] R 1 is a monocyclic or bicyclic aryl group or a monocyclic or bicyclic 5- to 10-membered heteroaryl group having 1 to 2 heteroatoms selected from the group consisting of N, S or 0 aryl or heteroaryl groups, independently of each other, may be substituted with substituent to three: F, Cl, Br, XOH, XOR 4, XOCOR 4, XOCONHR 4, XOCOOR 4, XCOR 4, XCN, XCOOH, XCOOR 4 , XCONH 2, XCONR 4 R 4 ', XCONHR 4, XCONHOH, XCONHOR 4, XCOSR 4, XSR 4, NO 2, XNHR 4, XNR 4 R 4', R 4 ( where, the two substituents R 1 if another They may be linked together in such a way that they form together methane di bisoxy, ethane-1,2-diybisoxy, propane-1,3-diyl, butane-1,4-diyl) Lt; RTI ID = 0.0 > (II) < / RTI > [224] Also, R 2 is a monocyclic or bicyclic aryl group or a monocyclic or bicyclic 5- to 10-membered heteroaryl group having 1 to 2 heteroatoms selected from the group consisting of N, S or 0 ( the above-mentioned aryl or heteroaryl groups, independently of each other, may be substituted with substituent to three: F, Cl, Br, XOH, XOR 4, XOCOR 4, XOCONHR 4, XOCOOR 4, XCOR 4, XC (NOH ) R 4, XC (NOR 4 ) R 4 ', XC (NO (COR 4)) R 4', XCN, XCOOH, XCOOR 4, XCONH 2, XCONR 4 R 4 ', XCONHR 4, XCONHOH, XCONHOR 4, XCOSR 4, XSR 4, XSOR 4, XSO 2 R 4, SO 2 NH 2, S0 2 NHR 4, SO 2 NR 4 R 4 ', N0 2, XNH 2, XNHR 4, XNR 4 R 4', XNHSO 2 R 4 , XN in the (SO 2 R 4) (SO 2 R 4 '), XNR 4 SO 2 R 4', XNHCOR 4, XNHCOOR 4, XNHCONHR 4, R 4 ( where two are If the substituents from each other ortho position of R 2 If present, they together with methane di bisoxy, ethane-1,2-diyl bisoxy, propane-1,3-diyl, butane- The use of the compound of formula (II), which means that can be connected to each other)) in such a way that sex is preferred. [225] In addition, R 3 are independently hydrogen, F, Cl, Br, XOH , XOR 4, XOCOR 4, XOCONHR 4, XOCOOR 4, XCOR 4, XC (NOH) R 4, XC (NOR 4) R 4 ', XC each other (NO (COR 4 )) R 4 ' , XCN, XSR 4 , XSOR 4 , XSO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 NR 4 R 4' , NO 2 , XNH 2 , XNHR 4 , One of XNR 4 R 4 ' , XNHSO 2 R 4 , XNR 4 SO 2 R 4' , XN (SO 2 R 4 ) (SO 2 R 4 ' ), XNHCOR 4 , XNHCOOR 4 , XNHCONHR 4 or R 4 Or two substituents where two substituents R < 3 > are, if they are in ortho position to each other, together they are selected from the group consisting of methandiylbisoxy, ethane-1,2-diylbisoxy, propane- Lt; RTI ID = 0.0 > (II) < / RTI > [226] R 4 and R 4 ' are independently of each other CF 3 , C 2 F 5 , C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 3-6 cycloalkyl, (C 1 3 alkyl-C 3-6 cycloalkyl), C 1-3 alkylaryl, C 1-3 alkylheteroaryl, monocyclic aryl, or 5- to 6-membered heteroatoms containing one or two N, S, or O atoms aryl (wherein aryl and heteroaryl groups F, Cl, Br, CH 3, C 2 H 5, NO 2, 1 or 2 from OCH 3, OC 2 H 5, CF 3, and the group consisting of C 2 F 5 Which may be substituted by a substituent or may carry an annelated methanediylbisoxy or ethane-1,2-diylbisoxy group; furthermore, one ring atom of the five membered cycloalkyl ring may be substituted by N or 0, one or two ring atoms of the six-membered cycloalkyl ring may be N and / or O, and the ring nitrogen may be optionally substituted with C 1-3 alkyl or C 1-3 alkanoyl. Chemistry means The use of a compound of formula II is preferred. [227] R 5 and R 5 ' are independently of each other C 1-6 alkyl, wherein one carbon atom may be replaced by 0, NH, NC 1-3 alkyl, NC 1-3 alkanoyl, or C 3 -7 -cycloalkyl-CO - 3alkyl wherein the ring atom of the 5-membered cycloalkyl ring may be N or 0, and one or two ring atoms of the 6- or 7-membered cycloalkyl ring may be substituted by N and / And the ring nitrogen may be optionally substituted with C 1-3 alkyl or C 1-3 alkanoyl; the above-mentioned C 1-6 alkyl moiety may be substituted with one of the above cycloalkyls, or N, S or O 1 to 2 5 to 6 membered heteroaryl may be substituted with an aromatic compound and having a heteroatom selected from; all alkyl and cycloalkyl portions referred to above is CF 3, OH, 2 of the group from consisting of OC 1-3 alkyl can be optionally substituted with a substituent of one or less, the above-mentioned heteroaryl group to obtain F, Cl, CF 3, CH 3, C 2 H 5, OCH 3, OC 2 H 5 Or the may be substituted with one or two substituents from the group of a), [228] Or R 5 and R 5 'can contain, one more oxygen, nitrogen or sulfur atom together with the N atom and C 1-4 alkyl, C 1-4 alkoxy -C 2 O-alkyl, C 1-4 alkoxy- Lt; RTI ID = 0.0 > 5-to 7-membered heterocyclic < / RTI > compound which may be substituted with a carbonyl, aminocarbonyl or phenyl. [229] Also, A is C 1-10 alkanediyl, C 2-10 Al canned yl, C 2-10 alkyne diyl, (C O-5 alkanediyl -C 3-7 cycloalkyl -C 0-5 alkanediyl al (C 0-5 alkanediyl-heteroarylene-C 0-5 alkanediyl), wherein the optionally present heteroaryl group is optionally substituted with F, Cl, Br, CH 3 , C 2 H 5 , NO 2 , OCH 3 , OC 2 H 5 , CF 3 , C 2 F 5 ; and in addition, one ring atom of the five-membered cycloalkyl ring may be substituted with N or O And one or two ring atoms in the 6- or 7-membered cycloalkyl ring may be N and / or O, and the ring nitrogen may be optionally substituted with C 1-3 alkyl or C 1-3 alkanoyl ; One or two carbon atoms in the aliphatic chain may be replaced by O, NH, NC 1-3 alkyl, NC 1-3 alkanoyl, NSO 2 C 1-3 alkyl; the alkyl or cycloalkyl moiety may be substituted with up to two F atom or OH, OC 1-3 alkyl, OC 1-3 alkanoyl, = O, NH 2 , NHC 1-3 alkyl, N (C 1-3 alkyl) 2 , NHC 1-3 alkanoyl, N (C 1-3 alkyl) (C 1-3 alkanoyl), NHCOOC 1-3 alkyl, NHCONHC 1- 3 alkyl, NHSO 2 C 1-3 alkyl, SH, use of the compound of formula (II), which means that may be substituted with one of the pieces of the substituents from the group consisting of SC 1-3 alkyl) is preferable. [230] B is selected from the group consisting of hydrogen, OH, OCOR 5 , OCONHR 5 , OCOOR 5 , COOH, COOR 5 , CONH 2 , CONHR 5 , CONR 5 R 5 ' , CONHOH, CONHOR 5 , Lt; RTI ID = 0.0 > (II) < / RTI > [231] Also, X is preferably a use of the compound of formula (II), which means a bond or CH 2. [232] Also preferred is the use of a compound of formula II wherein Y signifies a bond, O, S, NH, NR 4 , NCOR 4 or NSO 2 R 4 . [233] Example 307 describes a method for measuring inhibition of microglia activation. In this case, the activation of the microglial cells can be carried out using, for example, A -Peptides ( -Amyloid, Araujo, DM and Cotman, CM Brain Res. 569, 141-145 , Neuroinflammation: Mechanisms and Management, Humana Press (1999) J. Neurosci. , 19, 928-939, Wood, PL (1998) ). ≪ / RTI > For example, the compound of Example 49 and 6 - [[1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester has an IC 50 of 0.75 μm Showed inhibition [234] The stimulation by A [beta] -peptide is consistent with the pathological phenomenon of Alzheimer's disease. In the experiment, the material according to the invention showed inhibition of microglial activation when stimulated by A [beta] -peptide. Inhibition of microglial activation by a substance according to the present invention is associated with cytokine production and secretion (e.g., a large decrease in cytokine production and secretion (measured by ELISAN and mRNA expression assays) of II1 [beta] and TNF [alpha] / ≪ / RTI > nitrogen secretion. Several inflammatory factors are therefore equally inhibited. [235] The in vivo action of the substances according to the invention was shown in the MCAO model of rats. This model simulates the condition of a stroke. The material according to the invention reduces the activation of microglial cells, which occurs in the case of acute brain lesions in the animal brain. [236] The present invention also relates to the use of the compounds of formula (I) and (II) according to the invention for the preparation of pharmaceutical preparations for the prevention or treatment of diseases associated with microglial activation. Examples of such diseases include, but are not limited to, AIDS, dementia, amyotrophic lateral sclerosis, Creutzfeldt-Jakob disease, Down syndrome, diffuse rheumatoid disease, Huntington's disease, leukopenia, multiple sclerosis, Parkinson's disease, Pick's disease, Alzheimer's disease, to be. [237] The present invention also relates to pharmaceutical preparations comprising one or more compounds of formula (I) according to the invention and one or more excipients. The compositions or pharmaceutical preparations of the present invention are prepared in a known manner, in appropriate doses, together with solid or liquid excipients or diluents conventionally used according to the desired mode of administration and commonly used pharmaceutical and technical supplements. Preferred formulations are in the form of dosage forms suitable for oral, enteral or parenteral administration. Such dosage forms are, for example, in the form of tablet tablets, film tablet tablets, coated tablet tablets, pills, capsules, powders or depot as well as suppositories. For example, the active ingredient may be mixed with known adjuvants, for example inert diluents such as dextrose, sugar, sorbitol, mannitol, polyvinylpyrrolidone, explosives such as corn starch or alginic acid, binders such as starch or gelatin, A corresponding tablet tablet can be obtained by mixing a lubricant such as polymethylene, carboxymethylcellulose, cellulose acetate phthalate or polyvinyl acetate. Tablet tablets can also be made up of several layers. [238] Coated tablet tablets may be prepared by coating the cores prepared analogous to tablet tablets with materials commonly used in tablet tablet coatings, such as polyvinylpyrrolidone, Schellac, arabic gum, talc, titanium oxide or sugar . In this case, the coated tablet definition shell may also be composed of several layers, wherein the adjuvants mentioned above may be used for the tablet definition case. Capsules containing the active ingredient may also be prepared, for example, by mixing the active ingredient with an inert excipient such as lactose or sorbitol and encapsulating it in a gelatin capsule. [239] The substances according to the invention can also be used in a suitable solution, for example a physiological saline solution such as an infusion or injection. [240] In the case of parenteral dosing, particularly oily solutions, such as sesame oil, castor oil and cottonseed oil, are suitable. To increase the solubility, a solubilizing agent such as benzyl benzoate or benzyl alcohol may be added. [241] It is also possible to include the substance according to the present invention in the transdermal system and percutaneously administer it. [242] Dosages of the substances of the formula (I) and (II) according to the invention are determined by the attending physician according to the substance to be administered, the method of administration, the disease to be treated and the degree of the disease. The dosage per day is not more than 1000 mg, preferably not more than 100 mg, wherein the dosage can be a single dose administered at once a day or a multiple dose divided into two or more doses. [243] The compounds of formula I may exist in tautomers, stereoisomers or geometric isomers. The present invention also includes all possible isomers, including e-and z-isomers, S- and R-enantiomers, diastereoisomers, racemates and mixtures thereof, including tautomeric compounds. [244] The isomeric mixtures can be separated into enantiomers or E / Z isomers using methods commonly used, e. G., Crystallization, chromatography or salt production methods. [245] The preparation of the compounds according to the invention can be carried out, for example, analogously to the known processes described in the European patent (EP 531,883). If the preparation of the starting compound is not described, the starting compound is already known and readily available or its preparation is carried out analogously to the process described in this application. In the following, the preparation of some precursors, intermediates and products will be described by way of example. [246] In the production of the material according to the invention, for example, the following method is used: [247] General Methodology Guideline 1: [248] Reduction of nitro groups, hydrogenation of olefinic double bonds and hydrogenolysis of benzyl ethers [249] The compound to be reduced is dissolved in ethyl acetate, tetrahydrofuran, methanol or ethanol, or a mixture thereof and it is hydrogenated with 2-5% (relative to the nitro compound) with palladium on carbon at normal pressure. After the hydrogen uptake, it is sucked and the residue is washed with ethyl acetate or methanol or ethanol and the filtrate is concentrated by evaporation in vacuo. The crude product is generally allowed to react without further purification. [250] General Methodology Guideline 2: [251] Reduction of nitro group [252] 9.2 g of iron (II) sulfate are added to 30 ml of water and 9 ml of ammonia solution. A solution consisting of 3.6 mmol of the nitro compound in 100 ml of ethanol is added dropwise thereto and the suspension is stirred strongly at 70 캜 for 1 hour. Then, the solid is left to be filtered. The filtrate is concentrated by evaporation, mixed with water and extracted three times with ethyl acetate. The combined extracts are dried over sodium sulfate and evaporated in vacuo. This amino compound is used as a crude product in a later step. [253] General Methodology Guideline 3: [254] Cyclization of benzimidazoles with ortho esters [255] 10 mmol of 1,2-diaminobenzene derivative is dissolved in 25 ml of ethanol. 47 ml of a solution of 0.8 M HCl in ether is added dropwise thereto, stirred for 30 minutes and then evaporated to dryness in vacuo. The residue is recovered in 230 ml of methanol and mixed with 6 ml of trimethyl orthobenzoate or a corresponding amount of other orthoester. It is refluxed for 2-8 hours and poured into saturated sodium bicarbonate solution. After cooling, the mixture is extracted three times with ethyl acetate, and the combined extracts are dried over sodium sulfate and concentrated in vacuo. The residue is purified by crystallization or column chromatography on silica gel. [256] General Methodology Guideline 4: [257] Cyclization of benzimidazole with imino ester hydrochloride [258] 1.2 mmol of the 1,2-diaminobenzene derivative are dissolved in 5 ml of tetrahydrofuran, mixed with 1.5 mmol of benzimidated hydrochloride, and the mixture is stirred for 15 hours. The batch is mixed with saturated sodium bicarbonate solution, diluted with water and extracted three times with ethyl acetate. The collected organic phase was washed with 1N aq. Washed three times with hydrochloric acid, once with saturated sodium chloride solution, dried over sodium sulfate, filtered through frit with silica gel, and the solution is evaporated to dryness. The product is crystallized from diisopropyl ether. [259] General Methodology Guideline 5: [260] Cyclization to benzimidazole via carboxylic acid anilide. [261] 4.7 mmol of the 1,2-diaminobenzene derivative are dissolved in 20 ml of dichloromethane, mixed with 14 mmol of triethylamine, slowly stirred with 6 mmol of carboxylic acid chloride, and the mixture is stirred for 15 hours . The batch is mixed with saturated-sodium bicarbonate solution, diluted with water and extracted twice with dichloromethane. The combined organic phases are washed with water and saturated sodium chloride solution, dried over sodium sulfate and evaporated to dryness in vacuo. The remaining crude carboxylic acid anilide is recovered in a 9: 1 mixture of methanol and concentrated hydrochloric acid and refluxed for 1 hour. After cooling, the reaction mixture is slowly added to a saturated sodium bicarbonate solution, diluted with water and extracted three times with dichloromethane. The combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated by evaporation in vacuo. The residue is purified, if necessary, by crystallization or column chromatography on silica gel. [262] General Methodology Guideline 6: [263] Ether cleavage by hydrobromic acid [264] 5 g of aryl methyl ether are added to 160 ml of 48% aq. Mixed with HBr and refluxed for 1-5 hours. Cool and filter. The residue is recovered in ethyl acetate and extracted three times with saturated sodium bicarbonate solution. After drying over sodium sulfate, it is concentrated by evaporation in vacuo. The residue is purified, if necessary, by crystallization or column chromatography on silica gel. [265] General Methodology Guideline 7: [266] Ether cleavage by borontribromide [267] 1.86 mmol of arylmethyl ether are dissolved in 18 ml of dichloromethane and slowly mixed with 7.4 ml of a 1M solution of boron tribromide in 7.4 ml of dichloromethane at -35 ° C. After standing at -30 ° C for 12-15 hours, it is mixed with saturated sodium bicarbonate solution and extracted three times with dichloromethane. The combined extracts are dried over sodium sulfate and evaporated to dryness in vacuo. The residue is purified by column chromatography on silica gel, if necessary. [268] General Methodology Guideline 8: [269] Alkylation of hydroxybenzimidazole derivatives and phenol derivatives with alkyl halides [270] A solution of 1.85 mmol of the hydroxybenzimidazole derivative in 12 ml of N, N-dimethylformamide is mixed with 1.85 mmol of cesium carbonate and 2.24 mmol of alkyl bromide or alkyl iodide. If alkyl bromide is used, an optionally 1.85 mmol sodium iodide is added. After stirring for 12-96 hours, it is poured into water and recovered with ethyl acetate. The organic layer is washed 4 times with water, dried over sodium sulfate and evaporated to dryness in vacuo. [271] As an alternative to this aqueous recovery, the reaction mixture may be mixed with dichloromethane, the precipitated salt may be separated by filtration, and the filtrate may be concentrated by evaporation in vacuo. [272] Independent of the recovery method, the residue is purified by crystallization or column chromatography on silica gel. [273] General Methodology Guideline 9: [274] Saponification of carboxylic acid alkyl ester [275] 0.77 mmol of the carboxylic acid alkyl ester was dissolved in 5 ml of methanol and 5 ml of tetrahydrofuran and this was added to 5 ml of 0.5 N aq. Lithium or sodium hydroxide solution. The mixture was stirred for 2-12 hours, then almost concentrated by evaporation in vacuo, and aq. Hydrochloric acid is added to neutralize and extracted with ethyl acetate. It is dried over sodium sulfate and evaporated in vacuo. The residue is purified by column chromatography on silica gel, if necessary. [276] General Methodology Guideline 10: [277] Esterification of the carboxylic acid [278] 0.2 mmol of carboxylic acid are dissolved in 1 ml of primary or secondary alcohol and two drops of concentrated sulfuric acid are mixed and stirred for 12 hours at 60 ° C. The batch is mixed with a saturated potassium bicarbonate solution, diluted with water and extracted three times with ethyl acetate. The combined extracts are washed with saturated sodium chloride solution and then dried over sodium sulfate, which is concentrated by evaporation in vacuo and the residue is crystallized from diisopropyl ether. [279] General Methodology Guideline 11: [280] Reduction of Carboxylic Acid Alkyl Ester by Lithium Aluminum Hydride [281] 0.15 mmol of carboxylic acid ester is dissolved in tetrahydrofuran and mixed with 0.09 mmol of lithium aluminum hydride. It is stirred for 1-48 hours, mixed with water and extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate and evaporated in vacuo. The residue is purified, if necessary, by recrystallization or column chromatography on silica gel. [282] General Methodology Guideline 12: [283] Bithidic reaction of benzimidazolecarbaldehyde with (ω-carboxyalkyl) triphenylphosphonium bromide and esterification reaction with methanol [284] 2 mmol of (omega-carboxyalkyl) triphenylphosphonium bromide was mixed with 4 mmol of potassium-tert-butylate in 2.5 ml of dimethylsulfoxide and 2.5 ml of tetrahydrofuran at 0 ° C and stirred at T> 10 ° C After stirring for 30 minutes, a solution consisting of 0.67 mmol of aldehyde in 2 ml of tetrahydrofuran is added and the mixture is stirred at 20 < 0 > C for 3 hours. The batch was mixed with saturated ammonium chloride solution, diluted with water, extracted three times with ethyl acetate, and the combined organic phases were dried over sodium sulfate and concentrated by evaporation in vacuo. The residue is dissolved in 15 ml of methanol, mixed with 2 drops of concentrated sulfuric acid, and left for 48-72 hours. After evaporation in vacuo, the residue is purified by column chromatography on silica gel. [285] General Methodology Guideline 13: [286] Reaction of alkyl- and aryl sulfonic acid halides with aminobenzimidazole [287] 47 μmol of aminobenzimidazole derivative is dissolved in 0.5 ml of dichloromethane and mixed with 51 μmol of triethylamine and 51 μmol of alkyl- or arylsulfonic acid halide. The reaction mixture was stirred for 2-15 hours, saturated sodium bicarbonate solution was added for recovery and then extracted three times with chloromethane, and the combined organic phases were washed with water, dried over sodium sulfate and evaporated in vacuo . The residue is purified by crystallization or column chromatography on silica gel. [288] General Methodology Guideline 14: [289] Copper-mediated O- or N-arylation of benzimidazole [290] 5 mmol of N-unsubstituted benzimidazole derivative or N-aryl-substituted hydroxybenzimidazole derivative are dissolved in 20 ml of dichloromethane. 10 mmol of arylboronic acid, 5 mmol of anhydrous copper (II) acetate, 10 mmol of pyridine or triethylamine and about 2.5 g of molecular sieves (4) are added and stirred in a humid environment for 48-72 hours . And silica gel is added and it is evaporated from vacuum to dryness. The remaining powder is purified by chromatography on silica gel. The activity separates the regioisomeric N-arylated product. If necessary, use HPLC. [291] General Methodology Guideline 15: [292] Base-catalyzed N-substitution of benzimidazole [293] 5 mmol of N-unsubstituted benzimidazole derivative is dissolved in 20 ml of dimethylacetamide. 25 mmol of sodium hydride and 20 mmol of e-prearyl or heteroaryl halide are added and refluxed in a humidified environment for 48-72 hours. And silica gel is added and it is evaporated from vacuum to dryness. The remaining powder is purified by chromatography on silica gel. The activity separates the regioisomeric N-arylated product. If necessary, use HPLC. [294] General Methodology Guideline 16: [295] Cycling of benzimidazoles by aldehydes [296] 1 mmol of 1,2-diaminobenzene derivative is dissolved in 3 ml of nitrobenzene. 1 mmol of aryl- or heteroarylaldehyde is added thereto. This is heated to 150 DEG C for 2 to 6 hours and cooled. The residue is directly purified by chromatography on silica gel without further recovery. [297] General Methodology Guideline 17: [298] Conversion of carboxylic acid to carboxylic acid amide [299] 0.25 mmol of carboxylic acid are dissolved in 3 ml of N, N-dimethylformamide and mixed with 0.38 mmol of primary or secondary amine, 0.5 mmol of triethylamine and 0.25 mmol of diphenylphosphoryl azide. The mixture is stirred for 2 days. Water is added for recovery and it is extracted three times with ethyl acetate, and the combined organic phases are washed with water, dried over sodium sulfate and evaporated in vacuo. The residue is purified by chromatography on silica gel. [300] General Methodology Guideline 18: [301] Conversion of carboxylic acid ester to carboxylic acid amide [302] 0.36 mmol of amine are dissolved in 3 ml of toluene, cooled in an ice bath and mixed dropwise with 0.18 ml of a 2M solution of trimethylaluminum in toluene. It is mixed with a solution consisting of 0.33 mmol of carboxylic acid methyl ester in 3 ml of toluene and stirred at 95 ° C for 2-8 hours. Water is added for recovery, after cooling, extracted three times with ethyl acetate, the combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated by evaporation in vacuo. The residue is purified by chromatography on silica gel. [303] Example 1 [304] [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] acetic acid isopropyl ester [305] (Benincori, T .; Sannicolo, F .; J. Heterocycl. Chem .; 25: 1988; 1029- 1033) and bromoacetic acid isopropyl ester were reacted according to General Methods Guide 3. [306] Flash point 137-138 ° C [307] Example 2 [308] [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] ethan- [309] Was obtained by reacting [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] acetic acid methyl ester (DE 4330959) according to General Procedure Directive 11. [310] [311] Example 3 [312] 3 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] propan- [313] 0.5 g of 1,2-diphenyl-6-hydroxy-1H-benzimidazole were reacted with 3- (bromopropoxy) -tert-butyldimethylsilane according to the general method directive 8. After chromatography on silica gel, it was recovered with 2.5 ml of methanol, 0.4 ml of concentrated hydrochloric acid was added and stirred at 20 [deg.] C for 2 hours. Saturate it aq. Poured into sodium bicarbonate solution, extracted three times with ethyl acetate, and the combined extracts were washed with saturated aq. Washed with sodium chloride solution, then dried over sodium sulfate and evaporated in vacuo. [314] Flash point 191-193 ℃ [315] Example 4 [316] 3 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] propanoic acid [317] 100 mg of 3 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] propan-1-ol was placed in 2.5 ml of acetone and 0.15 ml of a Jones reagent solution Of chromium (VI) oxide, 1 ml of water and 0.23 ml of concentrated sulfuric acid). After stirring for 3.5 hours at -15 占 폚, isopropanol was added and quenched. This was diluted with water, extracted 3 times, dichloromethane, the combined organic phases were dried over sodium sulfate and concentrated in vacuo by evaporation. The residue was purified by chromatography on silica gel [318] [319] Example 5 [320] 3 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] propanoic acid methyl ester [321] 45 mg of 3 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] propanoic acid was dissolved in 0.5 ml of N, N-dimethylformamide, 41 mg of cesium carbonate and 10 Mu] l of iodide. It was stirred for 2 days, diluted with dichloromethane, filtered, and the filtrate was concentrated by evaporation in vacuo. The residue was then chromatographed on silica gel. [322] Flash point 120-121 DEG C [323] Example 6 [324] 2 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] propanoic acid methyl ester [325] Was obtained by reacting 1,2-diphenyl-6-hydroxy-1H-benzimidazole and 2-bromopropanoic acid methyl ester according to General Method Guide 8. [326] Flash point 132-135 ° C [327] Example 7 [328] 4 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] butanoic acid isopropyl ester [329] Was obtained by reacting 1,2-diphenyl-6-hydroxy-1H-benzimidazole and 4-bromobutanoic acid isopropyl ester according to General Method Guide 8. [330] Flash point 89-91 ℃ [331] Example 8 [332] 4 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] butan- [333] Was obtained by reacting 4 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] butanoic acid methyl ester according to General Method Guide 11. [334] Flash point 159-160 ℃ [335] Example 9 [336] Acetic acid - [4 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] [337] 1-ol was dissolved in 1 ml of dichloromethane, and 0.34 ml of pyridine and 20 占 퐇 of acetyl chloride were added to a solution of 50 mg of 4 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] After mixing with the lead, the mixture was stirred for 11 hours. It was mixed with a saturated sodium bicarbonate solution, diluted with water and extracted twice with dichloromethane. The combined organic phases were washed with saturated sodium chloride solution, then dried over sodium sulfate and evaporated in vacuo. The residue was purified using Thick-layer chromatography. [338] Flash point 68-69 ℃ [339] Example 10 [340] Yl)] - ester [0157] The title compound [341] Was prepared from 50 mg of 4 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] butan-1-ol, 0.34 ml of pyridine and 22 μl of trimethyl acetic acid chloride, Was prepared in a manner analogous to the instructions given in. [342] Flash point 104 - 106 ° C [343] Example 11 [344] 4 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] butyl-N-methylcarbamate [345] 1-ol was dissolved in 4 ml of dichloromethane and treated with 0.1 ml of triethylamine and 20 mg of methyl Mixture with isocyanate and stir for 15 hours. Add 0.1 ml of triethylamine and 20 mg of methyl isocyanate, stir for 20 hours and concentrate in vacuo. The residue is purified by chromatography on silica gel . [346] Flash point 124-126 ℃ [347] Example 12 [348] 5 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] pentanoic acid isopropyl ester 994 [349] Was obtained by reacting 1,2-diphenyl-6-hydroxy-1H-benzimidazole and 5-bromopentanoic acid isopropyl ester according to General Method Guide 8. [350] Flash point 91-92 ℃ [351] Example 13 [352] 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid methyl ester [353] Was obtained by reacting 1,2-diphenyl-6-hydroxy-1H-benzimidazole and 6-bromohexanoic acid methyl ester according to General Method Guide 8. [354] [355] Example 14 [356] 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid isopropyl ester [357] Was obtained by reacting 1,2-diphenyl-6-hydroxy-1H-benzimidazole and 6-bromohexanoic acid isopropyl ester according to General Method Guide 8. [358] [359] Example 15 [360] 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid [361] Was obtained by reacting 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid methyl ester according to General Method Guide 9. [362] [363] Example 16 [364] 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexan- [365] Was obtained by reacting 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid methyl ester according to General Method Guide 11. [366] [367] Example 17 [368] 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide [369] a) 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanonitrile [370] Was obtained by the reaction of 1,2-diphenyl-6-hydroxy-1H-benzimidazole and 6-bromohexanenonitrile according to General Method Guide 8. [371] Flash point 108-112 ° C [372] 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide [373] To a solution consisting of 50 mg of 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanonitrile in 1 ml methanol was added 18 mg of potassium carbonate and 40 μl of 30% hydrogen peroxide solution Was added and stirred for 24 hours, and ice-cooled aq. The sodium thiosulfate solution was stirred and extracted three times with ethyl acetate. After drying over sodium sulfate, it was concentrated by evaporation in vacuo. The residue was chromatographed on silica gel. [374] [375] Example 18 [376] Methoxy-6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide [377] 100 mg of 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid was dissolved in 2 ml of tetrahydrofuran, 39 mg of carbonyldiimidazole was mixed, Stirred at 20 [deg.] C for 30 minutes, and refluxed for 30 minutes. At 20 < 0 > C, 21 mg of O-methylhydroxyaminohydrochloride was added and stirred for 18 hours. The reaction mixture was diluted with ethyl acetate and washed with 2N aq. Hydrochloric acid and saturated potassium bicarbonate solution. After drying over sodium sulfate, it was concentrated by evaporation in vacuo. The residue was chromatographed on silica gel. [378] Flash point 144-145 ℃ [379] Example 19 [380] N- (phenylmethoxy) -6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide [381] Was obtained by reacting 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid and O-benzylhydroxylamino hydrochloride according to the general method instructions outlined in example 18 . [382] Flash point 144 ℃ [383] Example 20 [384] Hydroxy-6-1 (1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide [385] 6 mg of N- (phenylmethoxy) -6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide was dissolved in 4 ml of ethanol and 15 mg of palladium on carbon 10%) and stirred for 3 hours under a hydrogen atmosphere. After separating the catalyst, it was concentrated by evaporation in vacuo and the residue was crystallized from diethyl ether. [386] Flash point 83-85 ℃ [387] Example 21 [388] 7 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] heptanoic acid methyl ester [389] Was obtained by reacting 1,2-diphenyl-6-hydroxy-1H-benzimidazole with 7-bromoheptanoic acid methyl ester according to General Method Guide 8. [390] Flash point 77-80 ℃ [391] Example 22 [392] 7 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] heptanoic acid [393] Was obtained by the reaction of 7 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] heptanoic acid methyl ester according to General Method Guide 9. [394] Flash point 142-145 ° C [395] Example 23 [396] 7 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] heptanoic acid isopropyl ester [397] Was obtained by the reaction of 7 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] heptanoic acid with isopropanol according to General Procedure Directive 10. [398] Flash point 98-100 ° C [399] Example 24 [400] 6 - [[1- (3-nitrophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester [401] Benzimidazole (German patent DE 4330959) and 6-bromohexanoic acid isopropyl ester were reacted according to General Method Guide 8 to give 6-hydroxy-1- (3-nitrophenyl) -2-phenyl- . [402] Flash point 111-113 ° C [403] Example 25 [404] 6 - [[2-phenyl-1- [3- (trifluoromethyl) phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [405] a) (5-Methoxy-2-nitrophenyl) [(3-trifluoromethyl) phenyl] amine [406] 2 g of 3-fluoro-4-nitroanisole and 16 ml of 3- (trifluoromethyl) aniline were stirred at 140 DEG C for 72 hours. The batch was diluted with ethyl acetate and washed with 4N aq. Washed 10 times with hydrochloric acid and once with saturated sodium chloride solution. It was dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel. [407] 1 H-NMR (CDC1 3) δ = 3.78 ppm s (3H); 6.42 dd (J = 8, 2 Hz, 1H); 6.60 d (J = 2 Hz, 1H); 7.45-7.60 m (4H); 8.22 d (J = 8 Hz, 1H); 9.78 s (wide) (1H). [408] b) 6-Methoxy-2-phenyl-1 - [(3-trifluoromethyl) phenyl] -1H-benzimidazole [409] Was obtained by hydrogenation of (5-methoxy-2-nitrophenyl) [(3-trifluoromethyl) phenyl] amine according to general method guide 1 and subsequent cyclization with triethyl orthobenzoate according to general method 3. [410] Flash point 135-137 ° C [411] c) Preparation of 6-hydroxy-2-phenyl-1 - [(3-trifluoromethyl) phenyl] -1H-benzimidazole [412] Methoxy-2-phenyl-1 - [(3-trifluoromethyl) phenyl] -1H-benzimidazole was reacted according to General Procedure Guide 6. [413] 1 H-NMR (D 6 -DMSO): = 6.56 ppm d (J = 2 Hz, 1H); 6.82 dd (J = 8, 2 Hz, 1H); 7.32-7.50, m (5H); 7.60 d (J = 8 Hz, 1H); 7.70-7.95 m (4H); 9. 4 8 s (wide) (1H) [414] 6 - [[2-phenyl-1- [3- (trifluoromethyl) phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [415] Was obtained by reacting 6-hydroxy-2-phenyl-1 - [(trifluoromethyl) phenyl] -1H-benzimidazole and 6-bromohexanoic acid methyl ester according to General Method Guide 8. [416] Flash point 106-108 ℃ [417] Example 26 [418] 6 - [[2-phenyl-1- [3- (trifluoromethyl) phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid-isopropyl ester [419] Was obtained by reacting 6-hydroxy-2-phenyl-1 - [(trifluoromethyl) phenyl] -1H-benzimidazole with 6-bromohexanoic acid isopropyl ester according to General Method Guide 8. [420] Flash point 113-115 ℃ [421] Example 27 [422] 6 - [[2-phenyl-1- [3- (trifluoromethyl) phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid [423] Was obtained by reacting 6 - [[2-phenyl-1- [3- (trifluoromethyl) phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester according to General Method Guide 9. [424] Flash point 156-158 ℃ [425] Example 28 [426] 6 - [[2-phenyl-1- [3- (trifluoromethyl) phenyl] -1H-benzimidazol-6-yl] oxy] hexan- [427] Was obtained by reacting 6 - [[2-phenyl-1- [3- (trifluoromethyl) phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester according to General Method Guide 11. [428] Flash point 143-145 ℃ [429] Example 29 [430] 6 - [[1- (3-cyanophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [431] a) 3- (5-Methoxy-2-nitrophenyl) aminobenzonitrile [432] 2 g of 3-fluoro-4-nitroanisole and 15 ml of 3-aminobenzonitrile were stirred at 140 DEG C for 65 hours. The batch was diluted with ethyl acetate and washed three times with water and once with saturated sodium chloride solution. It was dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel. [433] Flash point 157-158 ℃ [434] b) 6-Methoxyl- (3-cyanophenyl) -2-phenyl-1H-benzimidazole [435] Was obtained by hydrogenation of 3- (5-methoxy-2-nitrophenyl) aminobenzonitrile according to general method 1 and subsequent cyclization with triethyl orthobenzoate according to general method 3. In the cyclization reaction, tetrahydrofuran was used as the solvent, unlike the general method instructions. [436] Flash point 185-191 ° C (decomposition) [437] c) Preparation of 6-hydroxy-1- (3-cyanophenyl) -2-phenyl-1H-benzimidazole [438] Was obtained by reacting 6-methoxyl- (3-cyanophenyl) -2-phenyl-1H-benzimidazole according to General Method Guide 7. [439] Flash point 216-218 ℃ [440] 6 - [[1- (3-cyanophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [441] Was obtained by reacting 6-hydroxy-1- (3-cyanophenyl) -2-phenyl-1H-benzimidazole and 6-bromohexanoic acid methyl ester according to General Method Guide 8. [442] Flash point 115-118 ℃ [443] Example 30 [444] 6 - [[1- (3-cyanophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester [445] Was obtained by reacting 6-hydroxy-1- (3-cyanophenyl) -2-phenyl-1H-benzimidazole and 6-bromohexanoic acid isopropyl ester according to General Method Guide 8. [446] Flash point 101-102 ℃ [447] Example 31 [448] 6 - [[1- (3-cyanophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid [449] Was obtained by reacting 6 - [[1- (3-cyanophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester according to General Method Guide 9. [450] Flash point 99-101 ℃ [451] Example 32 [452] 6 - [[1- (4-cyanophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [453] a) 4- (5-Methoxy-2-nitrophenyl) aminobenzonitrile [454] 2 g of 3-fluoro-4-nitroanisole and 15 ml of 4-aminobenzonitrile were stirred at 140 DEG C for 22 hours. The batch was diluted with ethyl acetate and washed with 2N aq. Washed twice with hydrochloric acid, three times with water and once with saturated sodium chloride solution. It was dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel. [455] 1 H-NMR (CDCl 3) δ = 3.70 ppm s (3H); 6.38 dd (J = 8, 2 Hz, 1H); 6.68 d (J = 2 Hz, 1H); 7.27 d (J = 8 Hz, 2H); 7.54 d (J = 8 Hz, 2H); 8.08 d (J = 8 Hz, 1H); 9.60 s (wide) (1H). [456] b) 6-Methoxyl- (4-cyanophenyl) -2-phenyl-1H-benzimidazole [457] Was obtained by hydrogenation of 4- (5-methoxy-2-nitrophenyl) aminobenzonitrile according to general method 1 and subsequent cyclization with triethyl orthobenzoate according to general method 3. Tetrahydrofuran was used as a solvent in the cyclization reaction, unlike the general procedure guidance. [458] [459] c) 6-Hydroxy-1- (4-cyanophenyl) -2-phenyl-1H-benzimidazole [460] Was obtained by reacting 6-methoxy-1- (4-cyanophenyl) -2-phenyl-1H-benzimidazole according to General Method Guide 7. [461] Flash point 266-268 ℃ [462] 6 - [[1- (4-cyanophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [463] Was obtained by reacting 6-hydroxy-1- (4-cyanophenyl) -2-phenyl-1H-benzimidazole and 6-bromohexanoic acid methyl ester according to General Method Guide 8. [464] Flash point 145-148 ° C [465] Example 33 [466] 6 - [[1- (4-cyanophenyl) -2-phenyl-1R-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester [467] Was obtained by reacting 6-hydroxy-1- (4-cyanophenyl) -2-phenyl-1H-benzimidazole and 6-bromohexanoic acid isopropyl ester according to General Method Guide 8. [468] Flash point 102-103 ℃ [469] Example 34 [470] 6 - [[1- (3-chlorophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [471] a) 1- (3-Chlorophenyl) -6-methoxy-2-phenyl-1H-benzimidazole [472] B: 69; 1970; 21 (2), < RTI ID = 0.0 > , 27) was reduced according to general method 2 and subsequently cyclized with diethyl orthobenzoate according to general method 3. [473] Flash point 140 - 143 ° C [474] b) 1- (3-Chlorophenyl) -6-hydroxy-2-phenyl-1H-benzimidazole [475] Was obtained by reacting 6-methoxy-1- (3-chlorophenyl) -2-phenyl-1H-benzimidazole according to General Method Guide 6. [476] Flash point 210-214 ℃ [477] 6 - [[(1-3-chlorophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [478] Was obtained by reacting 1- (3-chlorophenyl) -6-hydroxy-2-phenyl-1H-benzimidazole with 6-bromohexanoic acid methyl ester according to general method 8. [479] Flash point 101-1O5 ℃ [480] Example 35 [481] 6 - [[1- (3-chlorophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester [482] Was obtained by reacting 1- (3-chlorophenyl) -6-hydroxy-2-phenyl-1H-benzimidazole and 6-bromohexanoic acid isopropyl ester according to General Method Guide 8. [483] Flash point 107-112 ° C [484] Example 36 [485] 6 - [[1- (3-chlorophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid [486] Was prepared by the reaction of 6 - [[1- (3-chlorophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester according to General Method Guide 9. [487] [488] Example 37 [489] 6 - [[1- (3-chlorophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexan- [490] Was obtained by reacting 6 - [[1- (3-chlorophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester according to general procedure directive 11. [491] [492] Example 38 [493] 6 - [[1- (4-chlorophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [494] a) 1- (4-Chlorophenyl) -6-methoxy-2-phenyl-1H-benzimidazole [495] (Kottenhahn et al., J. Org. Chem .; 28; 1963; 3114, 3118) was reacted with (4-chlorophenyl) - (5-methoxy- Followed by cyclization with triethylorthobenzoate according to General Method Guide 3. [496] [497] b) l- (4-Chlorophenyl) -6-hydroxy-2-phenyl-lH-benzimidazole [498] Was obtained by reacting 6-methoxy-1- (4-chlorophenyl) -2-phenyl-1H-benzimidazole according to General Method Guide 6. [499] 1 H-NMR (D 6 -DMSO): = 6.60 ppm d (J = 2 Hz, 1H), 6.87 dd (J = 8, 2 Hz, 1H); 7.40-7.56 m (7H); 7.64 d (J = 8 Hz, 1H); 7.70 d (J = 8 Hz, 2H); 9.50 s (wide) (1H). [500] 6 - [[1- (4-chlorophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [501] Was obtained by reacting 1- (4-chlorophenyl) -6-hydroxy-2-phenyl-1H-benzimidazole and 6-bromohexanoic acid methyl ester according to General Method Guide 8. [502] Flash point 100-104 ℃ [503] Example 39 [504] 6 - [[1- (4-chlorophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester [505] Was obtained by reacting 1- (4-chlorophenyl) -6-hydroxy-2-phenyl-1H-benzimidazole and 6-bromohexanoic acid isopropyl ester according to General Method Guide 8. [506] Flash point 83-88 ℃ [507] Example 40 [508] 6 - [[1- (4-chlorophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid [509] Was prepared by the reaction of 6 - [[1- (4-chlorophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester according to General Method Guide 9. [510] [511] Example 41 [512] 6 - [[1- (4-chlorophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexan- [513] Was prepared by the reaction of 6 - [[1- (4-chlorophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester according to general procedure directive 11. [514] Flash point 115 - 120 ° C [515] Example 42 [516] 6 - [[1- (2-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [517] a) 5-Chloro-2-nitrophenyl-o-tolylamine [518] To a solution consisting of 10 g of 1-chloro-3,4-dinitrobenzene in 50 ml of ethanol was added 81 ml of o-toluidine and refluxed for 72 hours and it was concentrated in vacuo by evaporation. The residue was dissolved in ethyl acetate and 2N aq. Hydrochloric acid, and the organic phase was extracted with 3N hydrochloric acid more than 3 times, then it was dried over sodium sulfate and evaporated in vacuo. The residue was purified by chromatography on silica gel. [519] 1 H-NMR (CDCl 3 ): = 2.28 ppm s (3H); 6.70 dd (J = 10, 2 Hz, 1H); 6.80 d (J = 2 Hz, 1H); 7.22-7.40 m (4H); 8.18 d (J = 10 Hz, 1H); 9.40 s (wide) (1H). [520] b) 5-Methoxy-2-nitrophenyl-o-tolylamine [521] 1 g of 5-chloro-2-nitrophenyl-o-tolylamine was added to a solution consisting of 1 g of sodium in 20 ml of methanol, refluxed for 72 hours and cooled to 0 占 폚. The crystalline product was inhaled. [522] 1 H-NMR (CDCl 3 ): = 2.30 ppm s (3H); 3.72 s (3H); 6.19 d (J = 2 Hz, 1H); 6.32 dd (J = 10, 2 Hz, 1H); 7.20-7.40 m (4H); 8.20 d (J = 10 Hz, 1H); 9.62 s (wide) (1H). [523] c) Preparation of 6-methoxy-1- (2-methylphenyl) -2-phenyl-1H-benzimidazole [524] Was obtained by reacting 5-methoxy-2-nitrophenyl-o-tolylamine according to general method 1 and subsequent cyclization with triethyl orthobenzoate according to general method 3. [525] [526] 6 - [[1- (2-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [527] 6-Methoxy-1- (2-methylphenyl) -2-phenyl-1H-benzimidazole was reacted according to the general method directive 6. The crude product was reacted with 6-bromohexanoic acid methyl ester according to the general method directive 8. [528] [529] Example 43 [530] 6 - [[1- (2-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid [531] Was prepared by the reaction of 6 - [[1- (2-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester according to general procedure directive 9. [532] Flash point 198-200 ℃ [533] Example 44 [534] 6 - [[1- (3-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [535] a) 5-Chloro-2-nitrophenyl-m-tolylamine [536] 81 ml of m-toluidine was added to a solution consisting of 50 g of 1-chloro-3,4-dinitrobenzene in 250 ml of ethanol, and the solution was allowed to stand for 72 hours. The reaction was filtered, and the crystallization was washed with cold ethanol and 2N aq hydrochloric acid. Which was purified by chromatography on silica gel. [537] 1 H-NMR (CDCl 3 ): = 2.40 ppm s (3H); 6.72 dd (J = 10, 2 Hz, 1H); 7.04-7.13 m (3H); 7.14 d (J = 2 Hz, 1H); 7.32 t (J = 10 Hz, 1H); 8.18 d (J = 10 Hz, 1H); 9.52 s (wide) (1H). [538] b) 5-Methoxy-2-nitrophenyl-m-tolylamine [539] 39 g of 5-chloro-2-nitrophenyl-m-tolylamine were added to a solution consisting of 9 g of sodium in 670 ml of methanol and refluxed for 72 hours. It was then cooled to 0 C and the crystalline product was inhaled. [540] 1 H-NMR (CDCl 3 ): = 2.40 ppm s (3H); 3.73 s (3 H) 6.33 dd (J = 10, 2 Hz, 1 H); 6.58 d (J = 2 Hz, 1H); 7.03-7.15 m (3H); 7.31 t (J = 10 Hz, 1H); 8.19 d (J = 10 Hz, 1H); 9.72 s (wide) (1H). [541] c) 6-Methoxy-l- (3-methylphenyl) -2-phenyl-lH-benzimidazole [542] Was obtained by reacting 5-methoxy-2-nitrophenyl-m-tolylamine according to general method 1 and subsequent cyclization with triethyl orthobenzoate according to general method 3. [543] [544] d) 6-Hydroxy-1- (3-methylphenyl) -2-phenyl-1H-benzimidazole [545] Was obtained by reacting 6-methoxy-1- (3-methylphenyl) -2-phenyl-1H-benzimidazole according to General Method Guide 6. [546] 1 H-NMR (D6-DMSO ): δ = 2.34 ppm s (3H); 6.52 d (J = 2 Hz, 1H); 6.80 dd (J = 8, 2 Hz, 1H); 7.15 d (J = 8 Hz, 1H); 7.28 s (wide) (1H); 7.32-7.55 m (7H); 7.59 d (J = 8 Hz, 1H); 9.37 s (wide) (1H). [547] 6 - [[1- (3-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [548] Was obtained by reacting 6-hydroxy-1- (3-methylphenyl) -2-phenyl-1H-benzimidazole and 6-bromohexanoic acid methyl ester according to General Method Guide 8. [549] 1 H-NMR (CDCl 3 ): = 1.44-1.58 ppm m (2H); 1.64-1.85 m (4H); 2.35 t (J = 7.5 Hz, 2H); 2.40 s (3H); 3.68 s (3H); 3.95 t (J = 7.5 Hz, 2H); 6.70 d (J = 2 Hz, 1H); 6.96 dd (J = 8, 2 Hz, 1H); 7.10 d (J = 8 Hz, 1H); 7.16 s (broad) (2H); 7.25-7.43 m (4H); 7.55 dd (J = 8, 1 Hz, 2H), 7.77 d (J = 8 Hz, 1H). [550] Example 45 [551] 6 - [[1- (3-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester [552] Was obtained by reacting 6-hydroxy-1- (3-methylphenyl) -2-phenyl-1H-benzimidazole and 6-bromohexanoic acid isopropyl ester according to General Method Guide 8. [553] 1 H-NMR (CDCl 3) : δ = 1.22 ppm d (J = 8 Hz, 6H); 1.44-1.56 m (2H, CH2); 1.64-1.84 m (4H, CH2); 2.30 t (J = 7.5 Hz, 2H); 2.41 s (3H); 3.95 t (J = 7.5 Hz, 2H); 5.00 [delta] (J = 8 Hz, 1H); 6.68 d (J = 2 Hz, 1H); 6.96 dd (J = 8, 2 Hz, 1H); 7.10 d (J = 8 Hz, 1H); 7.14 s (broad) (1H); 7.25-7.41 m (4H); 7.54 dd (J = 8, 1 Hz, 2H); 7.75 d (J = 8 Hz, 1H). [554] Example 46 [555] 6 - [[1- (3-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid [556] Is obtained by reacting 6 - [[1- (3-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester according to General Method Guide 9. [557] 1 H-NMR (D 6 -DMSO): = 1.38-1.80 ppm m (6H); 2.23 t (J = 7.5 Hz, 2H); 3.84-3.93 m (2H); 6.60 d (J = 2 Hz, 1H); 6.87 d (broad) (J = 8 Hz, 1H); 7.15d (J = 8 Hz, 2H); 7.20-7.32 m (4H); 7.42-7.50 m (2H); 7.59 d (J = 8 Hz, 1H); 7.77 d (J = 8 Hz, 1H). [558] Example 47 [559] 6 - [[1- (3-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexan- [560] Was prepared by the reaction of 6 - [[1- (3-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester according to general procedure directive 11. [561] 1 H-NMR (CDCl 3) : δ = 1.40-1.85 m (8H); 2.40 s (3H); 3.68 t (J = 7.5 Hz, 2H); 3.96 t (J = 7.5 Hz, 2H); 6.69 d (J = 1.5 Hz, 1 H); 6.96 dd (J = 8, 1.5 Hz, 1H); 7.10 d (J = 8 Hz, 1H); 7.13 s (broad) (1H); 7.25-7.42 m (5H); 7.54 dd (J = 8, 1 Hz, 2H); 7.76 d (J = 8 Hz, 1H) [562] Example 48 [563] 6 - [[1- (4-methyl-1-phenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [564] a) 5-Chloro-2-nitrophenyl-p-tolylamine [565] Was prepared analogously to 5-chloro-2-nitrophenyl-m-tolylamine from 1-chloro-3,4-dinitrobenzene and p-tolylidine. This was crystallized and purified. [566] 1 H-NMR (CDCl 3 ): = 2.40 ppm s (3H); 6.70 dd (J = 10, 2 Hz, 1H), 7.08 d (J = 2 Hz, 1H); 7.16 d (J = 10 Hz, 2H); 7.28 d (J = 10 Hz, 2H); 8.18 d (J = 10 Hz, 1H); 9.50 s (broad) (1H). [567] b) 5-Methoxy-2-nitrophenyl-p-tolylamine [568] Was prepared analogously to 5-chloro-2-nitrophenyl-p-tolylamine and 5-methoxy-2-nitrophenyl-m-tolylamine from sodium methanolate. [569] 1 H-NMR (CDCl 3) : δ = 2.39 ppm s (3H); 3.72 s (3H); 6.31 dd (J = 10, 2 Hz, 1H); 6.50 d (J = 2 Hz, 1H); 7.19 d (J = 10 Hz, 2H); 7.25 d (J = 10 Hz, 2H); 8.19 d (J = 10 Hz, 1H); .9.70 s (broad) (1H). [570] c) Preparation of 6-methoxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazole [571] Methoxy-2-nitrophenyl-p-tolylamine was prepared according to general method 1 and subsequent cyclization with triethyl orthobenzoate according to general method 3. [572] 1 H-NMR (CDCl 3 ): = 2.49 ppm s (3H); 3.80 s (3H); 6. 69 d (J = 2 Hz, 1H); 6.97 dd (J = 8, 2 Hz, 1H); 7.20 d (broad) (J = 8 Hz, 2H); 7.25-7.36 m (5H); 7.53 dd (J = 8, 1 Hz, 2H); 7.76 d (J = 8 Hz, 1H). [573] d) 6-Hydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazole [574] Methoxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazole was obtained by reacting 6-methoxy-1- [575] 1 H-NMR (D 6 -DMSO): = 2.40 ppm s (3H); 6.50 d (J = 2 Hz, 1H); 6.80 dd (J = 8, 2 Hz, 1H); 7.28 d (J = 8 Hz, 2H); 7.32-7.43 m (5H); 7.46-7.52 m (2H); 7.56 d (J = 8 Hz, 1H); 9.28 s (broad) (1H). [576] 6 - [[1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [577] Was obtained by reacting 6-hydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazole with 6-bromohexanoic acid methyl ester according to General Method Guide 8. [578] [579] Example 49 [580] 6 - [[1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester [581] Was obtained by reacting 6-hydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazole with 6-bromohexanoic acid isopropyl ester according to General Method Guide 8. [582] [583] Example 50 [584] 6 - [[1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid [585] Was prepared by the reaction of 6 - [[1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester according to General Method Guide 9. [586] Flash point 186-190 ℃ [587] Example 51 [588] 6 - [[1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexan- [589] Was prepared by the reaction of 6 - [[1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester according to general procedure directive 11. [590] [591] Example 52 [592] 6 - [[1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [593] a) 3- (3,4-Di-methylphenyl) amino-4-nitrophenol [594] 3 g of 3-fluoro-4-nitrophenol and 6.9 g of 3,4-dimethylaniline were mixed and stirred at 150 DEG C for 2 hours. After cooling, it was dissolved in dichloromethane and treated with 1N aq. And extracted six times with hydrochloric acid. The organic phase was discarded, the combined aqueous phase was extracted three times with chloroform, the combined extracts were dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel. [595] 1 H-NMR (CDCl 3 / D 6 -DMSO): = 2.18 ppm s (6H); 6.13 dd (J = 8, 2 Hz, 1H); 6.36 d (J = 2 Hz, 1H); 6.90-7.00 m (2H); 7.09 d (J = 8 Hz, 1 H); 7.93 d (J = 8 Hz, 1H); 9.50 s (broad) (1H); 10.19 s (broad) (1H). [596] b) Preparation of 6- [3- (3,4-dimethylphenyl) amino-4-nitrophenyl] oxyhexanoic acid methyl ester [597] Was obtained by reacting 3- (3,4-dimethylphenyl) amino-4-nitrophenol with 6-bromohexanoic acid methyl ester according to General Method Guide 8. [598] 1 H-NMR (CDCl 3 ): = 1.38-1.52 ppm m (2H); 1.59-1.80 m (4H); 2.30 s (6 H); 2.33 (t, J = 7.5 Hz, 2H); 3.68 s (3H); 3.87 t (J = 7.5 Hz, 2H); 6.28 d (J = 8, 2 Hz, 1H); G.48 d (J = 2 Hz, 1H); 7.04 d (J = 8 Hz, 1 H); 7.06 s (broad) (1H); 7.18 d (J = 8 Hz, 1H); 8.17 d (J = 8 Hz, 1H): 9.71 s (broad) (, 1H). [599] 6 - [[1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [600] Amino-4-nitrophenyl] oxyhexanoic acid methyl ester was reacted according to General Method Guide 1, followed by cyclization with triethyl orthobenzoate according to General Method 3 . [601] 1 H- NMR (CDCl 3): δ = 1.44-1.56 ppm m (2H); 1.62-1.84 m (4H); 2.30 s (3H); 2.33 (t, J = 7.5 Hz, 2H); 2.34 s (3 H); 3.68 s (3H); 3.93 t (J = 7.5 Hz, 2H); 6.67 d (J = 2 Hz, 1H); 6.94 dd (J = 8, 2 Hz, 1H); 7.03 dd (J = 8, 1.5 Hz, 1H); 7.09 s (broad) (1H); 7.22-7.35 m (4H); 7.57 dd (J = 8, 1.5 Hz, 2H); 7.76 d (J = 8 Hz, 1H). [602] Example 53 [603] 6 - [[1- (3,4-di-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid [604] Was obtained by reacting 6 - [[1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester according to General Method Guide 9. [605] Flash point 158-161 ° C [606] Example 54 [607] 6 - [[1- (3,5-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [608] a) 3- (3,5-Dimethylphenyl) amino-4-nitrophenol [609] 5.4 g of 3-fluoro-4-nitrophenol and 4.3 ml of 3,5-dimethylaniline were mixed and stirred at 120 DEG C for 6 hours. After cooling, the mixture was recovered with ethyl acetate and water, extracted three times with 1N aq. Hydrochloric acid, and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and evaporated in vacuo. The residue was crystallized. [610] 1 H-NMR (D 6 -DMSO): = 2.30 ppm s (6H) 6.28 dd (J = 8, 2 Hz, 1H); 6.49 d (J = 2 Hz, 1 H); 6.52 d (J = 2 Hz, 1H); 6.90 s (broad) (1H); 6.98 s (broad) (2H); 8.04 d (J = 8 Hz, 1H); 9.51 s (broad) (1H). [611] b) Synthesis of 6- [3- (3,5-dimethylphenyl) amino-4-nitrophenyl] oxyhexanoic acid methyl ester [612] 3- (3,5-dimethylphenyl) amino-4-nitrophenol was reacted with 6-bromohexanoic acid methyl ester according to General Method Guide 8. [613] 1 H- NMR (CDCl 3): δ = 1.40-1.52 ppm m (2H); 1.60-1.80 m (4H); 2.30 t (J = 7.5 Hz, 2H); 2.32 s (6 H); 3.68 s (3H); 3.88 t (J = 7.5 Hz, 2H); 6.30 dd (J = 8, 2 Hz, 1H); 6.52 d (J = 2 Hz, 1H); 6.88 s (broad) (1H); 6.91 s (broad) (2H); 8.17 d (J = 8 Hz, 1H); 9.69 s (broad) (1H). [614] 6- [3- (3,5-dimethylphenyl) amino-4-nitrophenyl] oxyhexanoic acid methyl ester [615] Was prepared by reacting 6- [3- (3,5-dimethylphenyl) amino-4-nitrophenyl] oxyhexanoic acid methyl ester according to general method 1 and subsequent cyclization with triethyl orthobenzoate according to general method 3 . [616] Flash point 124-126 ℃ [617] Example 55 [618] 6 - [[1- (3,5-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid [619] Was obtained by reacting 6- [3- (3,5-dimethylphenyl) amino-4-nitrophenyl] oxyhexanoic acid methyl ester according to General Method Guide 9. [620] Flash point 162-164 ° C [621] Example 56 [622] 6 - [[1- (3,5-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester [623] Was obtained by the reaction of 6- [3- (3,5-dimethylphenyl) amino-4-nitrophenyl] oxyhexanoic acid with isopropanol in accordance with the General Method Guide 10. [624] Flash point 98-101 ℃ [625] Example 57 [626] 6 - [[1- (3-methoxyphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [627] a) 3- (3-Methoxyphenyl) amino-4-nitrophenol [628] 4 g of 3-fluoro-4-nitrophenol and 9.4 g of m-anisidine were mixed and stirred at 150 DEG C for 2.5 hours. After cooling, it was dissolved in dichloromethane, and 1N aq. Extracted three times with hydrochloric acid, the organic phase was dried over sodium sulfate and concentrated by evaporation in vacuo. The residue was chromatographed on silica gel. [629] 1 H-NMR (CDCl 3 ): = 3.83 ppm s (3H); 6.30 dd (J = 10, 2 Hz, 1H); 6.57 d (J = 2 Hz, 1H); 6.70-6.84 m (2H); 6.89 d (broad) (J = 10 Hz, 1H); 7.32 t (J = 10 Hz, 1H); 8.19 d (J = 10 Hz, 1H); 9.68 s (broad) (1H); 9.69 s (broad). [630] b) 6- [3- (3-methoxyphenyl) amino-4-nitrophenyl] oxyhexanoic acid methyl ester [631] Was obtained by reacting 3- (3-methoxy-phenyl) amino-4-nitrophenol and 6-bromohexanoic acid methyl ester according to General Method Guide 9. [632] 1 H- NMR (CDCl 3): δ = 1.42-1.58 ppm m (2H); 1.60-1.93 m (4H); 2.34 t (J = 7.5 Hz, 2H); 3.68 s (3H); 3.80 s (3H); 4.03 t (J = 7.5 Hz, 2H); 6.32 dd (J = 10, 2 Hz, 1H); 6.59 d (J = 2 Hz, 1 H); 6.68-6.84 m (2H); 6.90 d (broad) (J = 8 Hz, 1H): 7.32 t (J = 8 Hz, 1H); 8.19 d (J = 10 Hz, 1H); 9.70 s (broad) (1H). [633] c) Preparation of 6 - [[1- (3-methoxyphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [634] 6- [3- (3-methoxyphenyl) amino-4-nitrophenyl] oxyhexanoic acid methyl ester was reacted according to general method 1 and subsequently cyclized with triethyl orthobenzoate according to general method 3 . [635] 1 H- NMR (CDCl 3): δ = 1.44-1.58 ppm m (2H); 1.62-1.86 m (4H); 2.34 t (J = 7.5 Hz, 2H); 3.68 s (3H); 3.78 s (3H); 3.95 t (J = 7.5 Hz, 2H); 6.71 d (J = 1.5 Hz, 1 H); 6.83 dd (J = 1.5, 1.5 Hz, 1H); 6.90 dd (J = 8, 1.5 Hz, 1H); 6.94 dd (J = 8, 1.5 Hz, 1H); 7.01 dd (J = 8, 1.5 Hz, 1H); 7.27-7.36 m (3H); 7.40 t (J = 8 Hz, 1H); 7.56 dd (J = 8, 2 Hz, 2H); 7.74 d (J = 8 Hz, 1H). [636] Example 58 [637] 6 - [[1- (3-methoxyphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid [638] Was prepared by the reaction of 6 - [[1- (3-methoxy-phenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester according to general procedure directive 9. [639] Flash point 149-152 ℃ [640] Example 59 [641] 6 - [[1- (4-methoxyphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [642] a) 3- (4-Methoxyphenyl) amino-4-nitrophenol [643] 0.16 g of 3-fluoro-4-nitrophenol and 0.37 g of p-anisidine were mixed and stirred at 150 DEG C for 1.5 hours. After cooling, it was dissolved in dichloromethane, and 1N aq. Extracted twice with hydrochloric acid and once with saturated sodium chloride solution. The organic phase was dried over sodium sulfate and evaporated in vacuo. [644] 1 H- NMR (CDCl 3 / D 6 -DMSO): δ = 3.57 ppm s (3H); 6.6 dd (J = 10, 2 Hz, 1H); 6.18 d (J = 2 Hz, 1H); 6.77 d (J = 10 Hz, 2H); 7.03 d (J = 10 Hz, 2H); 7.89 d (J = 10 Hz, 1H); 9.40 s (broad) (1H); 9.80 s (broad). [645] b) 6- [3- (4-Methoxyphenyl) amino-4-nitrophenyl] oxyhexanoic acid methyl ester [646] Was obtained by reacting 3- (4-methoxy-phenyl) amino-4-nitrophenol and 6-bromohexanoic acid methyl ester according to General Method Guide 8. [647] 1 H- NMR (CDCl 3): δ = 1.38-1.50 ppm m (2H); 1.60-1.80 m (4H); 2.33 (t, J = 7.5 Hz, 2H); 3.67 s (3H); 3.SS t (J = 7.5 Hz, 2H); 3.88s (3H); 6.29 dd (J = 101.15 Hz, 1H); 6.30 d (J = 1.5 Hz, 1 H); 6.98 d (J = 10 Hz, 2H); 7.20 d (J = 10 Hz, 2H); 8.18 d (J = 10 Hz, 1H); 9.63 s (broad) (1H). [648] 6 - [[1- (4-methoxy-phenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [649] Is reacted with 6- [3- (4-methoxy-phenyl) amino-4-nitrophenyl] oxyhexanoic acid methyl ester according to General Method Guide 1 followed by cyclization with triethyl orthobenzoate . [650] Flash point 98-102 ℃ [651] Example 60 [652] 6 - [[1- (4-methoxyphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid [653] Was obtained by reacting 6 - [[1- (4-methoxyphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester according to General Method Guide 9. [654] Flash point 160-165 ° C [655] Example 61 [656] 6 - [[1- (3,4-dimethoxy-phenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [657] a) 3- (3,4-Dimethoxyphenyl) amino-4-nitrophenol [658] 3 g of 3-fluoro-4-nitrophenol and 8.8 g of 3,4-dimethoxyaniline were mixed and stirred at 150 DEG C for 2 hours. After cooling, it was dissolved in dichloromethane, and 1N aq. And extracted twice with hydrochloric acid. The aqueous phase was extracted twice with chloroform, and the chloroformic acid extract was dried over sodium sulfate and evaporated in vacuo. [659] 1 H-NMR (D 6 -DMSO): = 3.75 ppm s (3H); 3.78 s (3H); 6.25 dd (J = 10, 2 Hz, 1H); 6.35 d (J = 2 Hz, 1H); 6.88 dd (J = 8, 1.5 Hz, 1H); 6.98 d (J = 1.5 Hz, 1 H); 7.05 d (J = 8 Hz, 1H); 8.04 d (J = 10 Hz, 1H); 952 s (broad) (1H); 10.72 s (broad). [660] b) Synthesis of 6- [3- (3,4-dimethoxyphenyl) amino-4-nitrophenyl] oxyhexanoic acid methyl ester [661] Was obtained by reacting 3- (3,4-dimethoxy-phenyl) amino-4-nitrophenol and 6-bromohexanoic acid methyl ester according to General Method Guide 8. [662] 1 H- NMR (CDCl 3): δ = 1.40-1.52 ppm m (2H); 1.60-1.80 m (4H); 2.32 t (J = 7.5 Hz, 2H); 3.68 s (3H); 3.85 t (J = 7.5 Hz, 2H); 3.88 s (3 H); 3.93 s (3H); 6.29 dd (J = 10, 1.5 Hz, 1H); 6.33 d (J = 1.5 Hz, 1 H); 6.80 d (J = 1.5 Hz, 1 H); 6.87 dd (J = 10, 1.5 Hz, 1H); 6.92 d (J = 10 Hz, 1 H); 8.18 d (J = 10 Hz, 1H); 9.68 s (broad) (1H). [663] 6 - [[1- (3,4-dimethoxyphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [664] Was prepared by reacting 6- [3- (3,4-dimethoxy-phenyl) amino-4-nitrophenyl] oxyhexanoic acid methyl ester according to General Method Guide 1 followed by triethylorthobenzoate ≪ / RTI > [665] Flash point 116-118 ° C [666] Example 62 [667] 6 - [[1- (3,4-dimethoxyphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid [668] 6-yl] oxy] hexanoic acid methyl ester was reacted according to the General Method Guide 9 to give the title compound as a white amorphous solid. [669] Flash point 158-161 ° C [670] Example 63 [671] 6 - [[1- [3,4- (methylenedioxy) phenyl] -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [672] a) 3- (3,4-Methylenedioxyphenyl) amino-4-nitrophenol [673] 0.86 g of 3-fluoro-4-nitrophenol and 2.25 g of 3,4-methylenedioaniline were mixed and stirred at 120 DEG C for 5 hours. The mixture was chromatographed on silica gel. [674] 1 H-NMR (D 6 -DMSO): = 6.02 ppm s (2H); 6.25 dd (J = 10, 2 Hz, 1H); 6.33 d (J = 2 Hz, 1H); 6.72 dd (J = 8, 1.5 Hz, 1H); 6.87 d (J = 1.5 Hz, 1 H); 7.05 d (J = 10 Hz, 1H); 8.18 d (J = 10 Hz, 1H); 9.52 s (broad) (1H). [675] b) 6- [3- (3,4-Methylenedioxy-phenyl) amino-4-nitrophenyl] oxy-hexanoic acid methyl ester [676] Was obtained by reacting 3- (3,4-methylenedioxyphenyl) amino-4-nitrophenol with 6-bromohexanoic acid methyl ester according to General Method Guide 8. [677] Flash point 108-111 ℃ [678] 6 - [[1- (3,4-methylenedioxy-phenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [679] Was prepared by reacting 6- [3- (3,4-methylenedioxyphenyl) amino-4-nitrophenyl] oxyhexanoic acid methyl ester according to General Method Guide 1 followed by triethylorthobenzoate ≪ / RTI > [680] [681] Example 64 [682] 6 - [[1- [3,4- (methylenedioxy) phenyl] -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid [683] Was obtained by reacting 6 - [[1- (3,4-methylenedioxy-phenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester according to general procedure directive 9. [684] Flash point 130 ℃ [685] Example 65 [686] 6 - [[2-phenyl-1- (3,4,5-trimethoxy-phenyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [687] a) 3- (3,4,5-trimethoxy-phenyl) amino-4-nitrophenol [688] 3.7 g of 3-fluoro-4-nitrophenol and 4.76 g of 3,4,5-trimethoxy aniline were mixed and stirred at 10O < 0 > C for 10 hours. After cooling, it was recovered with ethyl acetate and water and extracted three times with ethyl acetate. The collected organic phase was washed with 1N aq. Extracted three times with hydrochloric acid, and extracted once with saturated sodium chloride solution. Dried over sodium sulfate and evaporated to a very large extent in vacuo. The product was digested with diisopropyl ether. [689] 1 H-NMR (D 6 -DMSO ): δ = 3.70 ppm s (3H); 3.80 s (6 H); 6.28 dd (J = 10, 2 Hz, 1H); 6.53 d (J = 2 Hz, 1H); 6.70 s (2H); 8.05 d (J = 10 Hz, 1H); 9.50 s (broad) (1H); 10.71 s (broad). [690] b) Preparation of 6- [4-nitro-3 - [(3,4,5-trimethoxy-phenyl) amino] phenyl] oxyhexanoic acid methyl ester [691] Was obtained by reacting 4-nitro-3 - [(3,4,5-trimethoxy-phenyl) amino] phenol and 6-bromohexanoic acid methyl ester according to General Method Guide 8. [692] 1 H-NMR (CDCl 3 ): = 1.40-1.53 ppm m (2H); 1.60-182 m (4H); 2.32 t (J = 7.5 Hz, 2H); 3.67 s (3H); 3.85 s (6H); 3.88 t (J = 7.5 Hz, 2H); 3.90 s (3H); 6.30 dd (J = 10, 1.5 Hz, 1H); 6.50 d (J = 1.5 Hz, 1 H); 6.52 s (2H); 8.18 d (J 10 Hz, 1H); 9.68 s (broad) (1H). [693] 6 - [[2-phenyl-1- (3,4,5-tri-methoxy-phenyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [694] Amino] phenyl] oxy-hexanoic acid methyl ester is reacted according to General Method Guide 1, followed by the general method 3, Followed by cyclization with triethylorthobenzoate. [695] Flash point 128-130 ° C [696] Example 66 [697] 6 - [[2-phenyl-1- (3,4,5-trimethoxyphenyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid [698] Was obtained by reacting 6 - [[2-phenyl-1- (3,4,5-trimethoxyphenyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester according to General Method Guide 9. [699] Flash point 198-201 ℃ [700] Example 67 [701] 6 - [[2-phenyl-1- (3,4,5-trimethoxyphenyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester [702] Was obtained by the reaction of 6 - [[2-phenyl-1- (3,4,5-trimethoxyphenyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid with isopropanol according to the general method directive 10. [703] Flash point 98-1O1 ℃ [704] Example 68 [705] 6 - [[1- [4- (N, N-dimethylamino) phenyl] -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [706] a) N, N-dimethyl-N '- (S-chloro-2-nitrophenyl) benzene- [707] Was prepared analogously to 5-chloro-2-nitrophenyl-m-tolylamine from 1-chloro-3,4-dinitrobenzene and N, N-dimethyl-p-phenylenediamine. [708] [709] b) Synthesis of N, N-dimethyl-N '- (5-methoxy-2-nitrophenyl) benzene- [710] 24.9 g of N, N-dimethyl-N '- (5-chloro-2-nitrophenyl) benzene 1,4-diamine was added to a solution consisting of 8 g of sodium in 200 ml of methanol. The mixture was heated in an autoclave to 120 < 0 > C for 9 hours. After cooling, the crystalline product was inhaled. [711] [712] c) Preparation of 6-methoxy-1- [4- (N, N-dimethylamino) phenyl] -2-phenyl-1H-benzimidazole [713] N-dimethyl-N '- (5-methoxy-2-nitrophenyl) benzene-1,4-diamine is reacted according to the general method directive 1 and then the crude diamine is reacted With trimethyl orthobenzoate and the crude product was treated with 6N aq. And refluxed with hydrochloric acid for 1 hour. The reaction mixture was diluted with aq. It was basified with a sodium hydroxide solution and extracted with ethyl acetate. It was dried over sodium sulfate and evaporated in vacuo. [714] [715] d) Preparation of 6-hydroxy-1- [4- (N, N-dimethylamino) phenyl] -2-phenyl-1H-benzimidazole [716] Was obtained by reacting 6-methoxy-1- [4- (N, Ndimethylamino) phenyl] -2-phenyl-1H-benzimidazole according to the general method guide 6. [717] [718] 6 - [[1- [4- (N, N-dimethylamino) phenyl] -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [719] Was obtained by reacting 6-hydroxy-1- [4- (N, Ndimethylamino) phenyl] -2-phenyl-1H-benzimidazole with 6-bromohexanoic acid methyl ester according to General Method Guide 8. [720] [721] Example 69 [722] Phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid (hereinafter referred to as " [723] Phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester was reacted according to General Method Guide 9 to give 6 - [[1- [4- (N, N- dimethylamino) . [724] Flash point 210-213 ℃ [725] Example 70 [726] 6 - [[1- (4-biphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [727] a) 5-Chloro-2-nitrophenyl-4-biphenylamine [728] Was prepared from 1-chloro-3,4-dinitrobenzene and 4-biphenylamine analogously to 5-chloro-2-nitrophenyl-m-tolylamine, which was purified by chromatography on silica gel. [729] [730] b) 5-Methoxy-2-nitrophenyl-4-biphenylamine [731] Was prepared from 5-chloro-2-nitrophenyl-4-biphenylamine and sodium methanolate analogously to 5-methoxy-2-nitrophenyl-m-tolylamine. [732] Flash point 150-154 ℃ [733] b) l- (4-biphenyl) -6-methoxy-2-phenyl-lH-benzimidazole [734] Was obtained by reacting 5-methoxy-2-nitrophenyl-4 biphenylamine according to General Method Guide 1 followed by cyclization with triethylortho benzoate according to General Method 3. [735] Flash point 140-144 ° C [736] c) 1- (4-biphenyl) -6-hydroxy-2-phenyl-1H-benzimidazole [737] Was obtained by reacting 1- (4-biphenyl) -6-methoxy-2-phenyl-1H-benzimidazole according to General Method Guide 6. [738] Flash point 312 ° C [739] 6 - [[1- (4-biphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [740] Was obtained by reacting 1- (4-biphenyl) -6-hydroxy-2-phenyl-1H-benzimidazole with 6-bromohexanoic acid methyl ester according to General Method Guide 8. [741] Flash point 106-108 ℃ [742] Example 71 [743] 6 - [[1- (4-biphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid [744] Was prepared by the reaction of 6 - [[1- (4-biphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester according to general method directive 9. [745] [746] Example 72 [747] 6 - [[1- (2-naphthyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [748] a) 3- (2-Naphthylamino) -4-nitrophenol [749] 3 g of 3-fluoro-4-nitrophenol and 8.2 g of 2-naphthylamine were mixed and stirred at 180 DEG C for 8 hours. The mixture was recovered in chloroform and washed with 2N aq. And washed with hydrochloric acid. The organic phase was dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel. [750] [751] b) Synthesis of 6- [3- (2-naphthyl) amino-4-nitrophenyl] oxyhexanoic acid methyl ester [752] Was obtained by the reaction of 3- (2-naphthylamino) -4-nitrophenol with 6-bromohexanoic acid methyl ester according to general method 8. [753] [754] 6 - [[1- (2-naphthyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [755] Was obtained by reacting 6- [3- (2-naphthylamino) -4-nitrophenyl] oxyhexanoic acid methyl ester according to the general method instructions followed by triethyl orthobenzoate according to general method 3. [756] Flash point 111-114 ℃ [757] Example 73 [758] 6 - [[1- (2-naphthyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid [759] Was prepared by the reaction of 6 - [[1- (2-naphthyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester according to general procedure directive 9. [760] Flash point 170-175 ° C [761] Example 74 [762] 6 - [[1- (2-fluorenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [763] a) 3- (2-Fluorenylamino) -4-nitrophenol [764] 2.17 g of 3-fluoro-4-nitrophenol and 5 g of 2-aminofluorene were mixed and stirred at 140 DEG C for 9 hours. The crude mixture was recovered with ethyl acetate and water, washed with 1N aq. And washed with hydrochloric acid. The aqueous phase was extracted with ethyl acetate and the combined organic phases were washed with 2N aq. Washed three times with hydrochloric acid and once with saturated sodium chloride solution. It was dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel. [765] [766] b) 6- [3- (2-Fluorenylamino) -4-nitrophenyl] oxyhexanoic acid methyl ester [767] Was obtained by reacting 3- (2-fluorenylamino) -4-nitrophenol with 6-bromohexanoic acid methyl ester according to General Method Guide 8. [768] [769] 6 - [[1- (2-fluorenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [770] Amino-4-nitrophenyl] oxyhexanoic acid methyl ester was reacted according to general method 1 and subsequently cyclized to triethyl orthobenzoate according to general method 3 . [771] Flash point 125-128 ℃ [772] Example 75 [773] 6 - [[1-phenyl-2- [3- (trifluoromethyl) phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [774] a) Preparation of ethyl- (3-trifluoromethyl) benzimidate hydrochloride [775] 9.7 ml of 3- (trifluoromethyl) benzonitrile are dissolved in 12 ml of ethanol, cooled in an ice bath, and the solution is saturated with HCl gas. After 72 hours, the precipitated product was aspirated and washed with diethyl ether. [776] Flash point 131-133 ° C (decomposition) [777] b) 5-Methoxy-2-nitrophenyldiphenylamine [778] A solution of 2 g of 3-fluoro-4-nitroanisole in 16 ml aniline was heated at 140 DEG C for 24 hours. After cooling, the reaction mixture was recovered with ethyl acetate and washed with 2N aq. And extracted with hydrochloric acid. The organic phase was dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel. [779] [780] c) 4-Methoxy-N 2 -Phenyl-o-phenylenediamine [781] Was obtained by reacting 5-methoxy-2-nitrophenyldiphenylamine according to General Method Guide 1. [782] [783] d) 6-Methoxy-1-phenyl-2- [3- (trifluoromethyl) phenyl] -1H- [784] Was obtained by the reaction of 4-methoxy-N 2 -phenyl-o-phenylenediamine with ethyl- (3-trifluoromethyl) benzimidate hydrochloride according to general method 4. [785] Flash point 138-140 ° C [786] e) 6-Hydroxy-1-phenyl-2- [3- (trifluoromethyl) phenyl] -1H-benzimidazole [787] Methoxy-1-phenyl-2- [3- (trifluoromethyl) phenyl] -1H-benzimidazole was obtained according to General Procedure Guide 7. [788] [789] 6 - [[1-phenyl-2- [3- (trifluoromethyl) phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [790] Was obtained by reacting 6-hydroxy-1-phenyl-2- [3- (trifluoromethyl) phenyl] -1H-benzimidazole with 6-bromohexanoic acid methyl ester according to General Method Guide 8. [791] Flash point 63-70 ℃ [792] Example 76 [793] 6 - [[1-phenyl-2- [3- (trifluoromethyl) phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester [794] Was obtained by reacting 6-hydroxy-1-phenyl-2- [3- (trifluoromethyl) phenyl] -1H-benzimidazole with 6-bromohexanoic acid isopropyl ester according to General Method Guide 8. [795] Flash point 96-98 ℃ [796] Example 77 [797] 6 - [[1-phenyl-2- [3- (trifluoromethyl) phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid [798] Phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester was reacted according to the general method guide 9 to give 6 - [[1-phenyl- 2- [3- (trifluoromethyl) [799] [800] Example 78 [801] 6 - [[1-phenyl-2- [3- (trifluoromethyl) phenyl] -1H-benzimidazol-6-yl] oxy] hexan- [802] Phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester was reacted according to General Procedure Directive 11 to give 6 - [[1-phenyl- 2- [3- (trifluoromethyl) [803] [804] Example 79 [805] 6 - [[2- (3-chlorophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [806] a) 2- (3-Chlorophenyl-6-methoxy-1-phenyl-1H-benzimidazole [807] Methoxy-N 2 -phenyl-o-phenylenediamine with ethyl-3-chlorobenzimidate hydrochloride (DeWolfe and Augustine; J. Org. Chem .; 30: 699 Were prepared according to General Method 4, Reaction. [808] Flash point 149-151 ℃ [809] b) 2- (3-Chlorophenyl) -6-hydroxy-1-phenyl-1H-benzimidazole [810] Was obtained by reacting 2- (3-chlorophenyl) -6-methoxy-1-phenyl-1H-benzimidazole according to general method directive 7. [811] Flash point 199-202 ℃ [812] 6 - [[2- (3-chlorophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [813] Was obtained by the reaction of 2- (3-chlorophenyl) -6-hydroxy-1-phenyl-1H-benzimidazole with 6-bromohexanoic acid methyl ester according to general procedure directive 8. [814] Flash point 69-72 ° C [815] Example 80 [816] 6 - [[2- (3-chlorophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester [817] Was obtained by reacting 2- (3-chlorophenyl) -6-hydroxy-1-phenyl-1H-benzimidazole with 6-bromohexanoic acid isopropyl ester according to General Method Guide 8. [818] Flash point 98-100 ° C [819] Example 81 [820] 6 - [[2- (3-chlorophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid [821] Was prepared by the reaction of 6 - [[2- (3-chlorophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester according to general procedure directive 9. [822] Flash point 137-140 ° C [823] Example 82 [824] 6 - [[2- (3-chlorophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexan- [825] Was prepared by the reaction of 6 - [[2- (3-chlorophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester according to general procedure directive 11. [826] [827] Example 83 [828] 6 - [[2- (4-chlorophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [829] a) Ethyl-4-chlorobenzimidate hydrochloride [830] 10 g of 4-chlorobenzonitrile was dispersed in 12 ml of ethanol and dissolved by adding diethyl ether. Cooled in an ice bath and saturated with HCl gas. After 72 h the precipitate was aspirated and washed with diethyl ether. [831] Flash point 173-174 ℃ (decomposition) [832] a) 2- (4-Chlorophenyl) -6-methoxy-1-phenyl-1H-benzimidazole [833] Was obtained by the reaction of 4-methoxy-N 2 -phenyl-o-phenylenediamine with ethyl-4-chlorobenzimidate hydrochloride according to general method 4. [834] Flash point 162-164 ° C [835] b) 6- [2- (4-Chlorophenyl) -6-hydroxy-1-phenyl-1H-benzimidazole [836] Was obtained by reacting 2- (4-chlorophenyl) -6-methoxy-1-phenyl-1H-benzimidazole according to General Method Guide 7. [837] Flash point 246-250 ℃ [838] 6 - [[2- (4-chlorophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [839] Was obtained by reacting 2- (4-chlorophenyl) -6-hydroxy-1-phenyl-1H-benzimidazole with 6-bromohexanoic acid methyl ester according to General Method Guide 8. [840] Flash point 86-87 ℃ [841] Example 84 [842] 6 - [[2- (4-chlorophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester [843] Was obtained by reacting 2- (4-chlorophenyl) -6-hydroxy-1-phenyl-1H-benzimidazole with 6-bromohexanoic acid isopropyl ester according to General Method Guide 8. [844] Flash point 124-126 ℃ [845] Example 85 [846] 6 - [[2- (4-chlorophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid [847] Was obtained by reacting 6 - [(2- (4-chlorophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester according to General Method Guide 9. [848] [849] Example 86 [850] 6 - [[2- (4-chlorophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexan- [851] Was prepared by the reaction of 6 - [[2- (4-chlorophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester according to general procedure directive 11. [852] [853] Example 87 [854] 6 - [[2- (3-methylphenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [855] a) 6-Methoxy-2- (3-methylphenyl) -1-phenyl-1H-benzimidazole [856] Methoxy-N 2 -phenyl-o-phenylenediamine with ethyl-3-methylbenzimidate hydrochloride (DeWolfe and Augustine, J. Org. Chem .; 30: 699 ) According to General Methods Guide 4. [857] Flash point 156-158 ℃ [858] b) 6-Hydroxy-2- (3-methylphenyl) -1-phenyl-1H-benzimidazole [859] Methoxy-2- (3-methylphenyl) -1-phenyl-1H-benzimidazole was obtained by reacting 6-methoxy-2- [860] [861] 6 - [[2- (3-methylphenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [862] Was obtained by reacting 6-hydroxy-2- (3-methylphenyl) -1-phenyl-1H-benzimidazole with 6-bromohexanoic acid methyl ester according to General Method Guide 8. [863] Flash point 82-84 ℃ [864] Example 88 [865] 6 - [[2- (3-methylphenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester [866] Was obtained by reacting 6-hydroxy-2- (3-methylphenyl) -1-phenyl-1H-benzimidazole with 6-bromohexanoic acid isopropyl ester according to General Method Guide 8. [867] [868] Example 89 [869] 6 - [[2- (3-methylphenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid [870] Was obtained by the reaction of 6 - [[2- (3-methylphenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester according to General Method Guide 9. [871] [872] Example 90 [873] 6 - ([2- (3-methylphenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexan- [874] Was prepared by the reaction of 6 - [(2- (3-methylphenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester according to general procedure directive 9. [875] Flash point 92-94 ℃ [876] Example 91 [877] 6 - [[2- (4-methylphenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [878] a) 6-Methoxy-2- (4-methylphenyl) -1-phenyl-1H-benzimidazole [879] Methoxy-N 2 -phenyl-o-phenylenediamine with ethyl-4-methylbenzimidate hydrochloride (DeWolfe and Augustine, J. Org. Chem .; 30: 699 ) According to General Methods Guide 4. [880] Flash point 150-152 ℃ [881] b) 6-Hydroxy-2- (4-methylphenyl) -1-phenyl-1H-benzimidazole [882] Methoxy-2- (4-methylphenyl) -1-phenyl-1H-benzimidazole was obtained by reacting 6-methoxy-2- [883] Flash point 257-264 ℃ [884] 6 - [[2- (4-methylphenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [885] Was obtained by reacting 6-hydroxy-2- (4-methylphenyl) -1-phenyl-1H-benzimidazole with 6-bromohexanoic acid methyl ester according to General Method Guide 8. [886] Flash point 99-102 ℃ [887] Example 92 [888] 6 - [[2- (4-methylphenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester [889] Was obtained by reacting 6-hydroxy-2- (4-methylphenyl) -1-phenyl-1H-benzimidazole with 6-bromohexanoic acid isopropyl ester according to General Method Guide 8. [890] Flash point 107-109 ℃ [891] Example 93 [892] 6 - [[2- (4-methylphenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid [893] Was obtained by the reaction of 6 - [[2- (4-methylphenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester according to General Method Guide 9. [894] [895] Example 94 [896] 6 - [[2- (4-methylphenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexan- [897] Was prepared by the reaction of 6 - [[2- (4-methylphenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester according to general procedure directive 11. [898] Flash point 150-152 ℃ [899] Example 95 [900] 6 - [[1-phenyl-2- (4-pyridinyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [901] a) 6-Methoxy-1-phenyl-2- (4-pyridinyl) -1H-benzimidazole [902] 0.4 g of 4-methoxy-N 2 -phenyl-o-phenylenediamine was dissolved in 8 ml of N, N-dimethylformamide, and the solution was added with 0.7 g of ethyl-2-ethoxy- Quinoline-1-carboxylate and 0.34 g of isoniconic acid. It was stirred for 16 hours at 1000C, cooled and then mixed with water, extracted three times with ethyl acetate and the combined organic phases were washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated by evaporation in vacuo. After chromatographic purification on silica gel, the amide was dissolved in 5 ml of 6N aq. Hydrochloric acid and refluxed for 3 hours. After cooling, it was stirred in a saturated sodium bicarbonate solution, extracted three times with ethyl acetate, and the combined extracts were washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated by evaporation in vacuo. [903] [904] b) 6-Hydroxy-1-phenyl-2- (4-pyridinyl) -1H-benzimidazole [905] Methoxy-l-phenyl-2- (4-pyridinyl) lH-benzimidazole was obtained by reacting 6-methoxy-l-phenyl-2- [906] [907] 6 - [[1-phenyl-2- (4-pyridinyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [908] Was obtained by reacting 6-hydroxy-1-phenyl-2- (4-pyridinyl) 1H-benzimidazole according to General Method Guide 8. [909] Flash point 100-103 ℃ [910] Example 96 [911] 6 - [[1-phenyl-2- (4-pyridinyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid [912] Was prepared by the reaction of 6 - [[l-phenyl-2- (4-pyridinyl) -lH-benzimidazol-6-yl] oxy] hexanoic acid methyl ester according to general procedure directive 9. [913] Flash point 160-162 ° C [914] Example 97 [915] 6 - [(1,2-di-phenyl-5-nitro-1H-benzimidazol-6-yl) oxy] hexanoic acid methyl ester [916] a) 1,2-diphenyl-6-hydroxy-5-nitro-1H-benzimidazole [917] b) 1,2-diphenyl-6-hydroxy-7-nitro-1H-benzimidazole [918] c) 1,2-diphenyl-6-hydroxy-5,7-dinitro-1H-benzimidazole [919] 5 g of 1,2-diphenyl-6-hydroxy-1H-benzimidazole was dissolved in 45 ml of glacial acetic acid, and a solution consisting of 1.67 g of potassium nitrite in 15 ml of water was added dropwise at 10-15 캜 . The mixture was stirred in an ice bath for 2 hours and at 20 ° C for 2 hours. The reaction mixture was concentrated by evaporation in vacuo and purified by chromatography on silica gel. [920] [921] 6 - [(1,2-diphenyl-5-nitro-1H-benzimidazol-6-yl) oxy] hexanoic acid methyl ester [922] Was obtained by reacting 1,2-diphenyl-6-hydroxy-5-nitro-1H-benzimidazole with 6-bromohexanoic acid methyl ester according to General Method Guide 8. [923] Flash point 123 ℃ [924] Example 98 [925] 6 - [(1,2-diphenyl-5-nitro-1H-benzimidazol-6-yl) oxy] hexanoic acid isopropyl ester [926] Was obtained by reacting 1,2-diphenyl-6-hydroxy-5-nitro-1H-benzimidazole with 6-bromohexanoic acid isopropyl ester according to General Method Guide 8. [927] Flash point 115-117 ° C [928] Example 99 [929] 6 - [(1,2-D-1-phenyl-7-nitro-1H-benzimidazol-6-yl) oxy] hexanoic acid methyl ester [930] Was obtained by the reaction of 1,2-diphenyl-6-hydroxy-7-nitro-1H-benzimidazole with 6-bromohexanoic acid methyl ester according to general method 8. [931] Flash point 110-112 ° C [932] Example 100 [933] 6 - [(1,2-diphenyl-7-nitro-1H-benzimidazol-6-yl) oxy] hexanoic acid isopropyl ester [934] Was obtained by reacting 1,2-diphenyl-6-hydroxy-5-nitro-1H-benzimidazole with 6-bromohexanoic acid isopropyl ester according to General Method Guide 8. [935] Flash point 88 ° C [936] Example 101 [937] 6 - [(7-amino-1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid methyl ester [938] [0252] 340 mg of 6 - [(1,2-diphenyl-7-nitro-1H-benzimidazol-6-yl) oxy] hexanoic acid methyl ester was hydrogenated in Raney nickel ethanol in an autoclave at 50 & . After the hydrogen absorption was complete, the catalyst was filtered off and concentrated in vacuo. [939] Flash point 113-115 ℃ [940] Example 102 [941] 6 - [(7-amino-1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid isopropyl ester [942] Was prepared by reacting 6 - [(1,2-diphenyl-7-nitro-1H-benzimidazol-6-yl) oxy] hexanoic acid isopropyl ester in analogy to the guideline in Example 101. [943] [944] Example 103 [945] 6 - [(5,7-dinitro-1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid methyl ester [946] Was obtained by reacting 5,7-dinitro-l, 2-diphenyl-6-hydroxy-lH-benzimidazole with 6-bromohexanoic acid methyl ester according to General Method Guide 8. [947] Flash point 88-91 ℃ [948] Example 104 [949] 6 - [(5,7-dinitro-1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid isopropyl ester [950] Was obtained by reacting 5,7-dinitro-1, 2-diphenyl-6-hydroxy-1H-benzimidazole with 6-bromohexanoic acid isopropyl ester according to General Method Guide 9. [951] Flash point 92-93 ℃ [952] Example 105 [953] 6 - [[5- (acetylamino) -1,2-diphenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [954] a) 5-Fluoro-2,4-dinitrophenol [955] 0.41 g of 1,3-difluoro-4,6-dinitrobenzene were dissolved in 8 ml of 0.5 N aq. Sodium hydroxide solution and refluxed for 2 hours. After cooling, the mixture was diluted with water and extracted three times with diethyl ether. The aqueous phase was acidified with 1N hydrochloric acid and extracted with diethyl ether. The organic phase was dried over sodium sulfate and evaporated in vacuo. [956] [957] b) 2,4-dinitro-5-hydroxydiphenylamine [958] 100 [mu] l of aniline was added to a solution of 50 mg of 5-fluoro-2,4-dinitrophenol in 0.5 ml of ethanol. It was stirred for 30 minutes and allowed to stand for 15 hours. Inhale it and wash the solid with 1N aq. Washed with hydrochloric acid and dried in vacuo. [959] [960] c) Acetic acid- (2,4-dinitro-5-phenylamino) phenyl ester [961] 0.11 ml of acetic anhydride was added to 275 mg of 2,4-dinitro-5-hydroxydiphenylamine in 1 ml of pyridine, left in an ice bath for 30 minutes, and further prevented at 20 ° C for 1 hour. After dilution with ethyl acetate, it was added to ice-cooled 1N aq. Washed once with hydrochloric acid, once with saturated potassium bicarbonate solution, once with saturated sodium chloride solution, then dried over sodium sulfate and concentrated by evaporation in vacuo. [962] [963] d) Acetic acid- (1,2-diphenyl-6-hydroxy-1H-benzimidazol- [964] Was obtained by reacting acetic acid- (2,4-dinitro-5-phenylamino) phenyl ester according to General Method Guide 1 followed by cyclization with trimethyl orthobenzoate according to general method 3. [965] [966] 6 - [[5- (acetylamino) -1,2-diphenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [967] Was obtained by reacting acetic acid- (1,2-diphenyl-6-hydroxy-1H-benzimidazol-5-yl) amide with 6-bromohexanoic acid methyl ester according to General Method Guide 8. [968] Flash point 128-130 ° C [969] Example 106 [970] 6 - [(5-amino-1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid isopropyl ester [971] Was obtained by reacting 6 - [(1,2-diphenyl-5-nitro-1H-benzimidazol-6-yl) oxy] hexanoic acid isopropyl ester according to General Method Guide 1. [972] [973] Example 107 [974] 6 - [[5 - [[(4-bromophenyl) sulfonyl] amino] -1,2-diphenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester [975] 6 - [(5-amino-1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid isopropyl ester was reacted with 4-bromobenzenesulfonic chloride . [976] Flash point 173-175 ℃ [977] Example 108 [978] 6 - [(5-amino-1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid methyl ester [979] Was obtained by reacting 6 - [(1,2-diphenyl-5-nitro-1H-benzimidazol-6-yl) oxy] hexanoic acid methyl ester according to General Method Guide 1. [980] [981] Example 109 [982] 6 - [[5 - [[(4-chlorophenyl) sulfonyl] amino] -1,2-diphenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [983] 6 - [(5-amino-1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid methyl ester was reacted with 4-chlorobenzenesulfonic chloride according to general procedure directive 13. [984] Flash point 157-159 ℃ [985] Example 110 [986] 6 - [[5 - [[(4-chlorophenyl) sulfonyl] amino] -1,2-diphenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester [987] 6 - ((5-amino-1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid isopropyl ester was reacted with 4-chlorobenzenesulfonic chloride according to general procedure directive 13 . [988] Flash point 158-159 ℃ [989] Example 111 [990] 6 - [[5 - [[(4-chlorophenyl) sulfonyl] amino] -1,2-diphenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid [991] Amino] -1,2-diphenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester was prepared according to General Method Guide 9 Followed by reaction. [992] Flash point 201-203 ℃ [993] Example 112 [994] 6 - [[[1,2-diphenyl-5 - [[(3-methylphenyl) sulfonyl] amino] -1H-benzimidazol-6-yl] oxy] -hexanoic acid isopropyl ester [995] 6 - [(5-amino-1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid isopropyl ester was reacted with 3-methylbenzenesulfonic chloride according to general procedure directive 13 . [996] Flash point 149-151 ℃ [997] Example 113 Synthesis of [998] 6 - [[1, 2-diphenyl-S - [[(4-methylphenyl) sulfonyl] amino] -1H-benzimidazol-6-yl] oxy] -hexanoic acid isopropyl ester [999] 6 - ((5-amino-1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid isopropyl ester was reacted with 4-methylbenzenesulfonic chloride according to general procedure directive 13 . [1000] Flash point 139-141 ° C [1001] Example 114 [1002] 6 - [[1,2-diphenyl-5 - [[(4-methoxyphenyl) sulfonyl] amino] -1H-benzimidazol-6-yl] oxy] -hexanoic acid isopropyl ester [1003] 6 - [(5-amino-1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid isopropyl ester was reacted with 4-methoxybenzenesulfonic chloride according to general procedure directive 13 . [1004] [1005] Example 115 [1006] 6 - [[[1,2-diphenyl-S - [[[(4-trifluoromethyl) phenyl] sulfonyl] amino] -1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester [1007] 6 - [(5-amino-1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid isopropyl ester was reacted with 4- (trifluoromethyl) benzenesulfonic acid Chloride. [1008] Flash point 170-171 ℃ [1009] Example 116 [1010] 6 - [[5 - [[[4- (acetylamino) phenyl] sulfonyl] amino] -1,2-diphenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester [1011] 6 - [(5-amino-1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid isopropyl ester was reacted with 4- (acetylamino) benzenesulfonic chloride ≪ / RTI > [1012] Flash point 100 - 102 ° C [1013] Example 117 [1014] 6 - [[5 - [[bis (3-chlorophenyl) sulfonyl] amino] -1,2-diphenyl-1H-benzimidazol-6-yl] oxy] [1015] 6 - [(5-amino-1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid isopropyl ester was reacted with 3-chlorobenzenesulfonic chloride according to general procedure directive 13 . [1016] Flash point 163-167 ℃ [1017] Example 118 [1018] 6 - [[1,2-diphenyl-5- [(propylsulfonyl) amino] -1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester [1019] 6 - [(5-amino-1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid isopropyl ester was reacted with propanesulfonic acid chloride according to general procedure directive 13. [1020] Flash point 126-128 ℃ [1021] Example 119 [1022] 6 - [[5 - [(benzylsulfonyl) amino] -1,2-diphenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester [1023] 6-yl) oxy] hexanoic acid isopropyl ester was reacted with benzene methanesulfonyl chloride in accordance with the general method Guide 13. [1024] Flash point 137-138 ° C [1025] Example 120 [1026] 4 - [(1,2-diphenyl-1H-benzimidazol-6-yl] oxy] methylbenzoic acid methyl ester [1027] Was obtained by reacting 1,2-diphenyl-6-hydroxy-1H-benzimidazole with 4- (bromomethyl) -benzoic acid methyl ester according to General Method Guide 8. [1028] Flash point 180-184 ℃ [1029] Example 121 [1030] 4 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] methylbenzoic acid [1031] Was obtained by reacting 4 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] methylbenzoic acid methyl ester according to General Method Guide 9. [1032] [1033] Example 122 [1034] 4 - [[1- (3-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] methylbenzoic acid methyl ester [1035] Was obtained by reacting 6-hydroxy-1- (3-methylphenyl) -2-phenyl-1H-benzimidazole with 4- (bromomethyl) benzoic acid methyl ester according to General Method Guide 8. [1036] Flash point 138-142 ° C [1037] Example 123 [1038] 4 - [[1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] methylbenzoic acid methyl ester [1039] Was obtained by reacting 6-hydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazole with 4- (bromomethyl) benzoic acid methyl ester according to general method 8. [1040] Flash point 145-148 ° C [1041] Example 124 [1042] 2- [2 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] ethoxy] acetic acid-tert- butyl ester [1043] 1-ol was dispersed in 1.7 ml of toluene and 0.7 ml of tetrahydrofuran. 0.1 ml of bromoacetic acid-tert-butyl ester, 13 mg of tetrabutylammonium hydrogen sulfate and 1.45 ml of 32% sodium hydroxide solution were added, and it was stirred for 48 hours. An additional 0.1 ml of bromoacetic acid-tert-butyl ester and 13 mg of tetrabutylammonium hydrogen sulfate were added and the mixture was left in an ultrasonic bath for 48 hours. It was then diluted with water, extracted three times with toluene, and the combined organic phases were washed with water and saturated sodium chloride solution, dried over sodium sulfate and concentrated by evaporation in vacuo. The residue was chromatographed on silica gel. [1044] [1045] Example 125 [1046] 2- [2 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] ethoxy] acetic acid [1047] Ethoxy] acetic acid-tert-butyl ester was dissolved in 0.5 ml of trifluoroacetic acid, and a solution of 50 mg of 2- [2 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] Lt; / RTI > It was then diluted with water and extracted three times with ethyl acetate, and the combined organic phases were washed with saturated sodium chloride solution, dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel. [1048] Flash point 134-136 ° C [1049] Example 126 [1050] 2- [2 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] ethoxy] acetic acid methyl ester [1051] Ethoxy] acetic acid was dissolved in 0.4 ml of N, N-dimethylformamide, and 29 mg of cesium carbonate was added to a solution of 35 mg of 2- [2 - [(1,2-diphenyl-1H-benzimidazol- Carbonate and 50 [mu] l of methyl iodide. It was stirred for 20 hours, then it was concentrated by evaporation in vacuo and chromatographed on silica gel. [1052] [1053] Example 127 [1054] 3- [2 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] ethoxy] propanoic acid-tert-butyl ester [1055] 1-ol was dispersed in 1.7 ml of toluene and 0.7 ml of tetrahydrofuran. Butyl acrylate, 13 mg of tetrabutylammonium hydrogen sulfate, and 1.45 ml of 32% sodium hydroxide solution. It was stirred for 48 hours and an additional 60 l of acrylic acid-tert-butyl ester and 13 mg of tetrabutylammonium hydrogen sulfate were added. The mixture was allowed to stand in an ultrasonic bath for 48 hours, then diluted with water and extracted three times with toluene, and the combined organic phases were washed with water and saturated sodium chloride solution, dried over sodium sulfate, and concentrated by evaporation in vacuo. The residue was chromatographed on silica gel. [1056] [1057] Example 128 [1058] 3- [2 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] ethoxy] propanoic acid [1059] 50 mg of 3- [2 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] ethoxy lpropanoic acid tert-butyl ester was dissolved in 0.5 ml of trifluoroacetic acid Dissolved and stirred for 15 hours. It was then diluted with water and extracted three times with ethyl acetate, and the combined organic phases were washed with saturated sodium chloride solution, then dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel. [1060] [1061] Example 129 [1062] 3- [2 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] ethoxy] propanoic acid methyl ester [1063] 35 mg of 3- [2 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] ethoxy] propanoic acid was dissolved in 0.4 ml of N, N-dimethylformamide, 28 mg of cesium Carboxylate and 50 [mu] l of methyl iodide and stirred for 30 hours. It was then diluted with water and extracted three times with ethyl acetate, and the combined organic phases were washed with saturated sodium chloride solution, then dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel. [1064] Flash point 91-93 ℃ [1065] Example 130 [1066] 3- [3 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] propoxy] propanoic acid tert-butyl ester [1067] 0.2 g of 3 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] propan-1-ol was dispersed in 1.7 ml of toluene and 0.7 ml of tetrahydrofuran. Butyl ester, 13 mg of tetrabutylammonium hydrogen sulfate and 1.47 ml of 32% sodium hydroxide solution were added and stirred for 48 hours. An additional 60 의 of acrylic acid-tert-butyl ester and 13 mg of tetrabutylammonium hydrogen sulfate were added and the mixture was left in an ultrasonic bath for 48 hours. It was then diluted with water and extracted three times with toluene, and the combined organic phases were washed with water and saturated sodium chloride solution, then dried over sodium sulfate and concentrated by evaporation in vacuo. The residue was chromatographed on silica gel. [1068] Flash point 95-98 ℃ [1069] Example 131 [1070] (E / Z) -5- (1,2-diphenyl-1H-benzimidazol-6-yl) pent- [1071] a) 1,2-diphenyl-6-methyl-1H-benzimidazole [1072] 5.1 g of 5-methyl-2-nitrophenylamine are hydrogenated in 55 ml of ethanol according to the general method 1. [1073] The crude product was reacted with trimethyl orthobenzoate according to general method 3. [1074] Flash point 134-136 ° C [1075] b) 1,2-Diphenyl-lH-benzimidazole-6-carbaldehyde [1076] 1 g of 1,2-diphenyl-6-methyl-1H-benzimidazole was dispersed in 31 ml of 40% sulfuric acid and mixed with 13.5 g of cerium ammonium nitrate. It was stirred at 80 < 0 > C for 2.5 h, saturated aq. The sodium bicarbonate solution was carefully stirred. The mixture was extracted three times with ethyl acetate and the combined extracts were washed with saturated aq. Washed with sodium chloride solution, then dried over sodium sulfate and evaporated to dryness in vacuo. The residue was chromatographed on silica gel. [1077] [1078] (E / Z) -5- (1,2-diphenyl-1H-benzimidazol-6-yl) pent- [1079] Was obtained by reacting 1,2-diphenyl-1H-benzimidazole-6-carbaldehyde with 3-carboxypropyltriphenylphosphonium bromide according to general method directive 12. [1080] [1081] Example 132 [1082] E-5- (1,2-diphenyl-1H-benzimidazol-6-yl) pent- [1083] (E / Z) -5- (1,2-diphenyl-1H-benzimidazol-6-yl) pent-4-enoic acid methyl ester was reacted according to General Procedure Directive 9. [1084] [1085] Example 133 [1086] 5- (1,2-diphenyl-1H-benzimidazol-6-yl) pentanoic acid methyl ester [1087] Pentenoate-6-yl) pent-4-enoic acid methyl ester was reacted according to General Procedure Guide 1 to give (E / Z) -5- [1088] [1089] Example 134 [1090] 5- (1,2-diphenyl-1H-benzimidazol-6-yl) pentanoic acid [1091] Was obtained by reacting 5- (1,2-diphenyl-1H-benzimidazol-6-yl) pentanoic acid methyl ester according to General Method Guide 9. [1092] Flash point 192-193 ° C [1093] Example 135 [1094] (E / Z) -6- (1,2-diphenyl-1H-benzimidazol-6-yl) hex-5-enoic acid methyl ester [1095] Was obtained by reacting 1,2-diphenyl-1H-benzimidazole-6-carbaldehyde with 4-carboxybutyltriphenylphosphonium bromide according to general procedure directive 12. [1096] [1097] Example 136 [1098] (E / Z) -6- (1,2-diphenyl-1H-benzimidazol-6-yl) hex- [1099] (E / Z) -6- (1,2-diphenyl-1H-benzimidazol-6-yl) hex-5-enoic acid methyl ester according to General Method [1100] [1101] Example 137 [1102] 6- (1,2-diphenyl-1H-benzimidazol-6-yl) hexanoic acid methyl ester [1103] Was prepared by the reaction of (E / Z) -6- (1,2-diphenyl-1H-benzimidazol-6-yl) hex-5-enoic acid methyl ester according to general method 1. [1104] [1105] Example 138 [1106] 6- (1,2-diphenyl-1H-benzimidazol-6-yl) hexanoic acid [1107] Was obtained by the reaction of 6- (1,2-diphenyl-1H-benzimidazol-6-yl) hexanoic acid methyl ester according to General Method Guide 9. [1108] [1109] Example 139 [1110] (E / Z) -7- (1,2-diphenyl-1H-benzimidazol-6-yl) hept- [1111] Was obtained by reacting 1,2-diphenyl-1H-benzimidazole-6-carbaldehyde with 5-carboxypentyltriphenylphosphonium bromide according to general procedure directive 12. [1112] [1113] Example 140 [1114] (E / Z) -7- (1,2-diphenyl-1H-benzimidazol-6-yl) hept- [1115] (E / Z) -7- (1,2-diphenyl-1H-benzimidazol-6-yl) hept-6-enoic acid methyl ester was reacted according to the general method directive 9. [1116] [1117] Example 141 [1118] 7- (1,2-diphenyl-1H-benzimidazol-6-yl) heptanoic acid methyl ester [1119] Was prepared by the reaction of (E / Z) -7- (1,2-diphenyl-1H-benzimidazol-6-yl) hept-6-enoic acid methyl ester according to general method 1. [1120] [1121] Example 142 [ [1122] 7- (1,2-diphenyl-1H-benzimidazol-6-yl) heptanoic acid [1123] Was obtained by the reaction of 7- (1,2-diphenyl-1H-benzimidazol-6-yl) heptanoic acid methyl ester according to General Method Guide 9. [1124] Flash point 99-103 ℃ [1125] Example 143 [1126] N- (1,2-diphenyl-1H-benzimidazol-5-yl) benzenesulfonamide [1127] Example 144 [1128] N- (phenylsulfonyl) -N- (1,2-diphenyl-1H-benzimidazol-5-yl) benzenesulfonamide [1129] a) 5-Amino-1,2-diphenyl-1H-benzimidazole [1130] 2,4-diaminodiphenylamine was reacted with trimethyl orthobenzoate according to general procedure directive 3. [1131] [1132] 5-Amino-l, 2-diphenyl-lH-benzimidazole was reacted with benzenesulfonic chloride in accordance with the General Method Guide 13. [1133] 143: Flash point 196-205 ℃ [1134] 144: [1135] [1136] Example 145 [1137] 3-Chloro-N- (1,2-diphenyl-1H-benzimidazol-5-yl) benzenesulfonamide [1138] Example 146 [1139] (3-chlorophenyl) sulfonyl] -N- (1,2-diphenyl-1H-benzimidazol-5-yl) [1140] 5-Amino-l, 2-diphenyl-lH-benzimidazole was reacted with 3-chlorobenzenesulfonic acid chloride according to the general method Guide 13. [1141] 145: Flash point 160-162 DEG C [1142] 146: [1143] [1144] Example 147 [1145] 4-Chloro-N- (1,2-diphenyl-IR-benzimidazol-5-yl) benzenesulfonamide [1146] 5-Amino-l, 2-diphenyl-lH-benzimidazole was reacted with 4-chlorobenzenesulfonic acid chloride according to the General Method Guide 13. [1147] [1148] Example 148 [1149] 4-Bromo-N- (1,2-diphenyl-1H-benzimidazol-5-yl) benzenesulfonamide [1150] Example 149 [1151] N- (4-bromophenylsulfonyl) -N- (1,2-diphenyl-1H-benzimidazol-5-yl) -4-bromobenzenesulfonamide [1152] 5-Amino-l, 2-diphenyl-lH-benzimidazole was reacted with 4-bromobenzenesulfonic chloride in accordance with the General Method Guide 13. [1153] 148: Flash point 135-139 DEG C [1154] 149: [1155] [1156] Example 150 [1157] 4- (Trifluoromethyl) -N- (1,2-diphenyl-1H-benzimidazol-5-yl) benzenesulfonamide [1158] Example 151 [1159] -N- [(3-trifluoromethyl) phenylsulfonyl] - (3-trifluoromethyl) benzenesulfonamide [1160] 5-Amino-1,2-diphenyl-1H-benzimidazole was reacted with (3-trifluoromethyl) benzenesulfonyl chloride according to the general method directive 13. [1161] 150: Flash point 116-121 DEG C [1162] 151: Flash point 238-241 DEG C [1163] Example 152 [1164] Methyl-N- (1,2-diphenyl-1H-benzimidazol-5-yl) benzenesulfonamide [1165] Example 153 [1166] N- (1,2-diphenyl-1H-benzimidazol-5-yl) -N- (3-methylphenylsulfonyl) -3-methylbenzenesulfonamide [1167] 5-Amino-1,2-diphenyl-1H-benzimidazole was reacted with 3-methylbenzenesulfonic chloride in accordance with the general method guide 13. [1168] 152: Flash point 192-195 DEG C [1169] 153: Flash point 173-176 DEG C [1170] Example 154 [1171] Methyl-N- (1,2-diphenyl-1H-benzimidazol-5-yl) benzenesulfonamide [1172] Example 155 [1173] N- (1,2-diphenyl-1H-benzimidazol-5-yl) -N- (4-methylphenylsulfonyl) -4-methyl-benzenesulfonamide [1174] 5-Amino-l, 2-diphenyl-lH-benzimidazole was reacted with 4-methylbenzenesulfonic chloride in accordance with the General Method Guide 13. [1175] 154: [1176] [1177] 155: Flash point 234-236 DEG C [1178] Example 156 [1179] Methoxy-N- (1,2-diphenyl-1H-benzimidazol-5-yl) benzenesulfonamide [1180] Example 157 [1181] N- (1,2-diphenyl-1H-benzimidazol-5-yl) -N- (4-methoxyphenylsulfonyl) -4- methoxybenzenesulfonamide [1182] 5-Amino-l, 2-diphenyl-lH-benzimidazole was reacted with 4-methoxybenzenesulfonic acid chloride according to the general method Guide 13. [1183] 156: [1184] [1185] 157: [1186] [1187] Example 158 [1188] N- (1,2-diphenyl-1H-benzimidazol-5-yl) propanesulfonamide e [1189] Example 159 [1190] N- (1,2-diphenyl-1H-benzimidazol-5-yl) -N- (propylsulfonyl) -propanesulfonamide [1191] 5-Amino-1,2-diphenyl-1H-benzimidazole was reacted with propane benzenesulfonic chloride in accordance with the general method guide 13. [1192] 158: [1193] [1194] 159: [1195] [1196] Example 160 [1197] N- (1,2-diphenyl-1H-benzimidazol-5-yl) benzenemethanesulfonamide [1198] 5-Amino-l, 2-diphenyl-lH-benzimidazole was reacted with benzene methanesulfonic acid chloride according to the general method Guide 13. [1199] Flash point 185-188 ℃ [1200] Example 161 [1201] 6 - [[1,2-diphenyl-1H-benzimidazol-5-yl] amino] hexanoic acid methyl ester [1202] Example 162 [1203] - [(5-methoxycarbonyl) -pentyl] amino] hexanoic acid methyl ester [1204] 207 mg of 6-bromohexanoic acid methyl ester, 138 mg of potassium carbonate and 150 mg of sodium iodide are added to 285 mg of 5-amino-1,2-diphenyl-1H-benzimidazole in 5 ml of methanol , And it was stirred at 20 占 폚 for 3 days. It was mixed with water and extracted three times with ethyl acetate, and the combined organic phases were dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel. [1205] 161: Flash point 109-113 DEG C [1206] 162: [1207] [1208] Example 163 [1209] 6 - [[1,2-diphenyl-1H-benzimidazol-5-yl] amino] hexanoic acid [1210] Was prepared by the reaction of 6 - [[1,2-diphenyl-1H-benzimidazol-5-yl] amino] hexanoic acid methyl ester according to General Method Guide 9. [1211] [1212] Example 164 [1213] 6 - [[2-phenyl-1- [4- (phenylmethoxy) phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1214] a) (5-Hydroxy-2-nitrophenyl) [(4- (phenylmethoxy) phenyl] amine [1215] 1 g of 3-fluoro-4-nitrophenol and 3.8 g of 4-benzyloxyaniline were stirred at 150 DEG C for 6.5 hours. The batch was diluted with dichloromethane and washed with 1N aq. Extraction with hydrochloric acid and washing with water were repeated twice, then 2N aq. And extracted twice with sodium hydroxide solution. The base aqueous phase was washed with ethyl acetate and 1N aq. And mixed with hydrochloric acid. After phase separation, the organic layer was washed with 1N aq. And extracted several times with hydrochloric acid. After washing the organic phase with saturated sodium chloride solution, it was dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel. [1216] [1217] b) Preparation of 6 - [[4-nitro-3 - [[4- (phenylmethoxy) phenyl] amino] phenyl] oxy] hexanoic acid methyl ester [1218] Was obtained by the reaction of (5-hydroxy-2-nitrophenyl) [(4 (phenylmethoxy) phenyl] amine with 6-bromohexanoic acid methyl ester according to General Method Guide 8. [1219] [1220] 6 - [[2-phenyl-1- [4- (phenylmethoxy) phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1221] Phenyl] oxy] hexanoic acid methyl ester was reduced in accordance with the general method directive 2, followed by reduction with trimethyl ortho (trimethylsilyl) amide according to general method 3, Benzoate. ≪ / RTI > [1222] [1223] Example 165 [1224] 6 - [[2-phenyl-1- [4- (phenylmethoxy) phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid [1225] 6 - [[2-phenyl-1- [4- (phenylmethoxy) phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester was reacted according to the general method directive 9. [1226] [1227] Example 166 [1228] 6 - [[1- (4-hydroxyphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid [1229] 6 - [[2-phenyl-1- [4- (phenylmethoxy) phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid was reacted according to the General Method Guide 1. [1230] [1231] Example 167 [1232] 6 - [[2-phenyl-1- [3- (phenylmethoxy) phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1233] a) (5-Hydroxy-2-nitrophenyl) [(3- (phenylmethoxy) phenyl] amine [1234] 1 g of 3-fluoro-4-nitrophenol and 3.81 g of 3-benzyloxyaniline were stirred at 150 DEG C for 22 hours. It was then recovered with a small amount of dichloromethane and directly chromatographed on silica gel. [1235] [1236] b) 6 - [[4-Nitro-3 - [[3- (phenylmethoxy) phenyl] amino] phenyl] -oxy] hexanoic acid methyl ester [1237] Was obtained by the reaction of (5-hydroxy-2-nitrophenyl) [(3 (phenylmethoxy) phenyl] amine with 6-bromohexanoic acid methyl ester according to General Method Guide 8. [1238] [1239] 6 - [[2-phenyl-1- [3- (phenylmethoxy) phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1240] Phenyl] oxy] hexanoic acid methyl ester was reduced in accordance with the General Method Guide 2, followed by the reduction of trimethyl ortho (4-nitro-3 - [[ Benzoate. ≪ / RTI > [1241] [1242] Example 168 [1243] 6 - [[2-phenyl-1- [3- (phenylmethoxy) phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid [1244] 6 - [[2-phenyl-1- [3- (phenylmethoxy) phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester was reacted according to the general method directive 9. [1245] [1246] Example 169 [1247] 6 - [[1- (3-hydroxyphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid [1248] 6 - [[2-phenyl-1- [3- (phenylmethoxy) phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid was reacted according to General Methods Guide 1. [1249] [1250] Example 170 [1251] 6 - [[1- (3-hydroxy-phenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1252] 6 - [[2-phenyl-1- [3- (phenylmethoxy) phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester was reacted according to General Method Guide 1. [1253] [1254] Example 171 [1255] 6 - [[1- (3-nitrophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid ethyl ester [1256] Was obtained by reacting 6-hydroxy-1- (3-nitrophenyl) -2-phenylbenzimidazole (German patent DE 4330959) with 6-bromohexanoic acid ethyl ester according to general procedure directive 8. [1257] Flash point 104 - 106 ° C [1258] Example 172 [1259] 6 - [[4-bromo-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1260] a) 4-Bromo-6-methoxy-2-phenyl-1H-benzimidazole [1261] 36.6 g of 4-amino-3-bromo-5-nitroanisole (J. Chem. Soc. 1966, 1769) were placed in 750 ml of ethanol and mixed with 19.8 g of iron powder and 126 ml of acetic acid. After stirring for 2.5 hours at 55 [deg.] C, it was mixed with 350 ml of dichloromethane. It was made basic with 2N sodium hydroxide solution. After filtration through celite, it was washed with water and saturated brine, and concentrated by evaporation. The resulting crude phenyldiamine was reacted with trimethyl orthobenzoate according to General Methods Guide 3. [1262] Flash point 203-205 ℃ [1263] b) 4-Bromo-6-methoxy-l- (4-methylphenyl) -2-phenyl-lH-benzimidazole [1264] Bromo-6-methoxy-2-phenyl-1H-benzimidazole and 2.24 g of 4- (methylbenzene) boronic acid were added to a solution of 1.5 g of anhydrous copper (II) 3 g of molecular sieves at < RTI ID = 0.0 > 1000 C < / RTI > for 7 hours. After addition of dichloromethane and celite, it was concentrated by evaporation and chromatographed on silica gel with a hexane / ethyl acetate mixture. [1265] Flash point 209-210 ° C [1266] c) 4-Bromo-6-hydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazole [1267] Bromo-6-methoxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazole, 6 ml of acetic acid and 6 ml of aq. Hydrobromic acid (62%) was boiled for 5.5 hours. After that, it was precipitated in water and the precipitate was inhaled. The residue was dispersed in ethyl acetate and 2N sodium hydroxide solution, and the organic phase was washed with water and then concentrated by evaporation. [1268] Flash point 136-137 ° C [1269] 6 - [[4-bromo-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1270] Was obtained by reacting 4-bromo-6-hydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazole with 6-bromohexanoic acid methyl ester according to General Method Guide 8. [1271] Flash point 136 ℃ [1272] Example 173 [1273] 6 - [[4-acetyl-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1274] Hydroxyphenyl) -2-phenyl-1H-benzimidazole, 0.37 ml of (alpha-ethoxyvinyl) tributyltin and 140 mg of dichlorobis (4-methylphenyl) Triphenylphosphine) palladium were stirred at 10O < 0 > C in 10 ml of toluene for 18 hours. After cooling, it is washed with 2N aq. Hydrochloric acid for 0.25 h. After phase separation, the organic phase was washed with water and concentrated by evaporation. The residue was chromatographed on silica gel with a hexane / ethyl acetate mixture. [1275] Flash point 114-115 ° C [1276] Example 174 [1277] 6 - [[1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-5-yl] oxy] hexanoic acid methyl ester [1278] a) 5-Methoxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazole [1279] 16.8 g of 5-methoxy-2-phenyl-1H-benzimidazole (Bull Sci Fichem Ind. Bologna, 11 1953, 42) and 20.4 g 4- (methylbenzene) Reaction was carried out according to Directive 14. [1280] [1281] In addition, 6-methoxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazole was obtained. [1282] b) 5-Hydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazole [1283] Was obtained from 5-methoxy-l- (4-methylphenyl) -2-phenyl-lH-benzimidazole according to general procedure directive 6. [1284] Flash point 270 ℃ [1285] 6 - [[1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-5-yl] oxy] hexanoic acid methyl ester [1286] Was obtained by the reaction of 5-hydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazole with 6-bromohexanoic acid methyl ester according to General Method Guide 8. [1287] [1288] Example 175 [1289] 6 - [[1- (4-methylphenyl) -2-phenyl-IR-benzimidazol-5-yl] oxy] hexanoic acid [1290] Was obtained from 6 - [[1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-5-yl] oxy] hexanoic acid methyl ester according to general procedure directive 9. [1291] [1292] Example 176 [1293] 6 - [[2-phenyl-1- [4- (thiomethyl) phenyl] -1H-benzimidazol-5yl] oxy] hexanoic acid methyl ester [1294] a) 6 - [[2-phenyl] -1H-benzimidazol-5-yl] oxy] hexanoic acid methyl ester [1295] 4,84 g of 2-phenyl-5-hydroxy-1H-benzimidazole (Izv. Akad. Nauk. SSSR Ser. Chim. 8 1990,1888) was reacted with 6- . [1296] [1297] 6 - [[2-phenyl-1- [4- (thiomethyl) phenyl] -1H-benzimidazol-5yl] oxy] hexanoic acid methyl ester [1298] Was obtained by the reaction of 6 - [[2-phenyl] -1H-benzimidazol-5-yl] oxy] hexanoic acid methyl ester with 4- (thiomethylbenzene) boronic acid according to General Method Guide 14. [1299] [1300] Example 177 [1301] 6 - [[2-phenyl-1 - [(4-thiomethyl) phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1302] Was obtained by reacting 6 - ([2-phenyl] -1H-benzimidazol-5-yl] oxy] hexanoic acid methyl ester with 4- (thiomethylbenzene) boronic acid according to General Method Guide 14. [1303] [1304] Example 178 [1305] 6 - [[2-phenyl-1- (3-thienyl) -1H-benzimidazol-5-yl] oxy] hexanoic acid methyl ester [1306] Was obtained by the reaction of 6 - [[2-phenyl] -1H-benzimidazol-5-yl] oxy] hexanoic acid methyl ester with thiophene- [1307] [1308] Example 179 [1309] 6 - [[2-phenyl-1- (3-thienyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1310] Was obtained by the reaction of 6 - [[2-phenyl] -1H-benzimidazol-5-yl] oxy] hexanoic acid methyl ester with thiophene- [1311] [1312] Example 180 [1313] Phenyl] -1H-benzimidazol-6-yl] oxy] phenoxy] butanoic acid methyl ester [1314] a) 6- (3-Methoxyphenoxy) -1- (4-methylphenyl) -2-phenyl-1H-benzimidazole [1315] Was obtained from 6-hydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazole and 3-methoxybenzeneboronic acid according to general procedure directive 14. [1316] Flash point 120-122 ° C [1317] b) Preparation of 3 - [[1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] [1318] (3-methoxyphenoxy) -1- (4-methylphenyl) -2-phenyl-1H-benzimidazole was reacted with 10 mol% of hexadecyl tributylphosphonium bromide in accordance with the general method Followed by reaction. [1319] Flash point 252-253 ℃ [1320] Phenyl] -1H-benzimidazol-6-yl] oxy] phenoxy] butanoic acid methyl ester [1321] Was obtained by the reaction of 3 - [[1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] phenol with 4-bromobutyric acid methyl ester according to general procedure directive 8. [1322] [1323] Example 181 [1324] Phenyl] -1H-benzimidazol-6-yl] oxy] phenoxy] butanoic acid methyl ester [1325] a) 6- (4-Methoxy-phenoxy) -1- (4-methylphenyl) -2-phenyl-1H-benzimidazole [1326] Was obtained from 6-hydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazole and 4-methoxybenzeneboronic acid according to general procedure directive 14. [1327] [1328] b) Preparation of 4 - [[1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] [1329] (3-methoxyphenoxy) -1- (4-methylphenyl) -2-phenyl-1H-benzimidazole was reacted with 10 mol% of hexadecyl tributylphosphonium bromide in accordance with the general method Followed by reaction. [1330] [1331] Phenyl] -1H-benzimidazol-6-yl] oxy] phenoxy] butanoic acid methyl ester [1332] Was obtained by reacting 4 - [[1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] phenol with 4-bromobutyric acid methyl ester according to General Method Guide 8. [1333] [1334] Example 182 [1335] [4 - [[1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] phenoxy] acetic acid methyl ester [1336] Was obtained by reacting 4 - [[1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] phenol and bromoacetic acid methyl ester according to General Method Guide 8. [1337] [1338] Example 183 [1339] 4 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] butanoic acid methyl ester [1340] Was obtained by reacting 1,2-diphenyl-6-hydroxy-1H-benzimidazole and 4-bromobutanoic acid methyl ester according to General Method Guide 8. [1341] Flash point 107-110 ° C [1342] Example 184 [1343] 6 - [[2-phenyl-1- (3-pyridyl) -1H-benzimidazol-5-yl] oxy] hexanoic acid methyl ester [1344] Phenyl] -1H-benzimidazol-5-yl] oxy] hexanoic acid methyl ester and pyridine-3-boronic acid were reacted according to the general method guide 14. [1345] MS (EI): 415 (molecular ion peak) [1346] Example 185 [1347] 6 - [[2-phenyl-1- (3-pyridyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1348] Phenyl] -1H-benzimidazol-5-yl] oxy] hexanoic acid methyl ester and pyridine-3-boronic acid were reacted according to the general method guide 14. [1349] MS (EI): 415 (molecular ion peak) [1350] Example 186 [1351] 6- [12-phenyl-1- (2-pyridyl) -1H-benzimidazol-5-yl] oxy] hexanoic acid [1352] Was obtained by the reaction of 6 - [[2-phenyl] -1H-benzimidazol-s-yl] oxy] hexanoic acid methyl ester and 2-fluoro-pyridine according to General Method Guide 15. [1353] MS (EI): 401 (molecular ion peak) [1354] Example 187 [1355] 6 - [[2-phenyl-1- (2-pyridyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid [1356] Was obtained by the reaction of 6 - [[2-phenyl] -1H-benzimidazol-5-yl] oxy] hexanoic acid methyl ester with 2-fluoro-pyridine according to General Procedure Guide 15. [1357] MS (EI): 401 (molecular ion peak) [1358] Example 188 [1359] 6 - [[2-phenyl-1- (4-pyridyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1360] Phenyl] -1H-benzimidazol-5-yl] oxy] hexanoic acid methyl ester and pyridine-4-boronic acid were reacted according to the general method guide 14. [1361] MS (EI): 415 (molecular ion peak) [1362] Example 189 [1363] 6 - [[2- (4-fluorophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1364] Was obtained by reacting 6 - [(4-amino-3 (phenylamino) phenyl] oxy] hexanoic acid methyl ester and 4-fluorobenzoyl chloride according to General Method Guide 5. [1365] MS (ET): 432 (molecular ion peak) [1366] Example 190 [1367] 6 - [[2- (4-methoxy-phenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1368] Was obtained by reacting 6 - [[4-amino-3- (phenylamino) phenyl] oxy] hexanoic acid methyl ester and 4-methoxybenzoyl chloride according to general method 5. [1369] MS (EI): 444 (molecular ion peak) [1370] Example 191 [1371] 6 - [[2- (3-fluorophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1372] Was obtained by reacting 6 - [[4-amino-3 (phenylamino) phenyl] oxy] hexanoic acid methyl ester and 3-fluorobenzoyl chloride according to General Method Guide 5. [1373] MS (EI): 432 (molecular ion peak) [1374] Example 192 [1375] 6 - [[2- (4-bromophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1376] Was obtained by reacting 6 - [[4-amino-3 (phenylamino) phenyl] oxy] hexanoic acid methyl ester with 4-bromobenzoyl chloride in accordance with the General Method Guide 5. [1377] MS (EI): 492/494 (molecular ion peak) [1378] Example 193 [1379] 6 - [[2- [4- (trifluoromethyl) phenyl] -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1380] Was reacted with 6 - [[4-amino-3- (phenylamino) phenyl] oxy] hexanoic acid methyl ester and 4- (trifluoromethyl) benzoyl chloride according to General Methods Guide 5. [1381] MS (EI): 482 (molecular ion peak) [1382] Example 194 [1383] 6 - [[2- (4-fluorophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid. [1384] Was obtained by reacting 6 - [[2- (4-fluorophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester according to General Method Guide 9. [1385] MS (EI): 418 (molecular ion peak) [1386] Example 195 [1387] 6 - [[l-phenyl-2- (benzothiene-2-yl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1388] Was obtained by the reaction of 6 - [[4-amino-3- (phenylamino) phenyl] oxy] hexanoic acid methyl ester with benzothiophene-2-carboxylic acid chloride according to the general method directive 5. [1389] Flash point 129-130 ° C [1390] Example 196 [1391] 6 - [[1-phenyl-2- (benzothiene-2-yl) -1H-benzimidazol-6-yl] oxy] hexanoic acid [1392] Were prepared in accordance with General Methods Directive 9. [1393] Flash point 340 ° C (decomposition) [1394] Example 197, [1395] 6 - [[5-hydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester [1396] Example 198 [1397] 6 - [[6-hydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-5-yl] oxy] hexanoic acid isopropyl ester [1398] 4,5-dimethoxy-1,2-dinitrobenzene is hydrogenated to the diamino compound according to General Method Guide 1 and the compound is cyclized with trimethyl orthobenzoate according to General Method 3 to give 5,6- Dimethoxy-2-phenyl-1H-benzimidazole (flash point 131-133 [deg.] C). This benzimidazole derivative is converted to 5,6-dimethoxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazole (flash point 145-148 ° C) by reacting with 4-methylphenylboronic acid according to General Method . Following ether cleavage with hydrobromic acid of 5,6-dihydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazole according to General Methodology Guideline ( 1 H-NMR of hydrobromide (D 6 -DMSO) = 2.42 ppm s (3H); 6.68 s (1H); 7.22 s (1H); 7.40-7.62 m (1OH)), which was obtained from 6-bromohexanoic acid isopropyl ester 8 < / RTI > 6 - [[6-hydroxy-1- (4-methylphenyl) 6-yl] oxy] hexanoic acid isopropyl ester (a flash point of 177-178 占 폚). [1399] Example 199 [1400] 6 - [[5-hydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid [1401] Were prepared according to the General Method Guide 9. [1402] Flash point 245-248 ℃ [1403] Example 200 [1404] 6 - [[6-hydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-5-yl] oxy] hexanoic acid [1405] Were prepared according to the General Method Guide 9. [1406] Flash point 182-184 ℃ [1407] Example 201 [1408] 6 - [[5-methoxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester [1409] 6-yl] oxy] hexanoic acid isopropyl ester was methylated with methyl iodide according to the general method directive 8 to give methyl 6-methyl- did. [1410] Flash point 89-91 ℃ [1411] Example 202 [1412] 6 - [[5-methoxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid [1413] Were prepared in accordance with General Methods Directive 9. [1414] Flash point 184-186 ° C [1415] Example 203 [1416] 6 - [[5-hydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1417] And [1418] Example 204 [1419] 6 - [[6-hydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-5- yl] oxy] [1420] Is prepared analogously to the isopropyl ester by alkylation of 5,6-dihydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazole in accordance with the general method Directive 8 with 6-bromohexanoic acid methyl ester . 6 - [[5-hydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester. [1421] 1 H-NMR (CDC1 3) 1.45-1.58 ppm m (2H); 1.65-1.90 m (4H); 2.37 t (J = 7.5 Hz, 2H); 2.48 s (3H); 3.68 s (3H); 3.98 t (J = 7.5 Hz, 2H); 5.68 s (wide) (1H, OH); 6.62 s (1H); 7.18 d (J = 8 Hz, 2H); 7.22-7.38 m (5H); 7.40 s (1H); 7.53 dd (J = 8, 1 Hz, 2H) [1422] And 6 - [[6-hydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-5-yl] oxy] hexanoic acid methyl ester. [1423] Flash point 141-143 ° C [1424] Example 205 [1425] 6 - [[5-methoxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1426] 6-yl] oxy] hexanoic acid was dissolved in 2 ml of methanol, and 1 drop of concentrated sulfuric acid was added to the solution of 40 mg of 6 - [[5-methoxy-1- (4-methylphenyl) Mixed. The mixture was stirred for 2 hours, and it was mixed with a saturated potassium bicarbonate solution, then diluted with water and extracted with ethyl acetate. The extract was dried over sodium sulfate and evaporated in vacuo. The residue was crystallized from diisopropyl ether. [1427] Flash point 81-82 ℃ [1428] Example 206 [1429] 6 - [[6-methoxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-5- yl] oxy] [1430] 6-Hydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-5-yl] oxy] hexanoic acid methyl ester was methylated with methyl iodide according to general method . [1431] Flash point 108-110 ° C [1432] Example 207 [1433] 6 - [[6-methoxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-5-yl] oxy] hexanoic acid [1434] Were prepared according to the General Method Guide 9. [1435] Flash point 182-184 ℃ [1436] Example 208 [1437] 6 - [(5-amino-1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl) oxy] [1438] a) 3 - [(3,4-Dimethylphenyl) amino] -4,6-dinitrophenol [1439] 6.6 g of 3,4-dimethylaniline were added to a suspension composed of 4 g of 4,6-dinitro-3-fluorophenol (J. Org. Chem. I991, 5958) in 100 ml of ethanol. It was stirred at 40 < 0 > C for 7 days. After cooling, it was sucked and the residue was recrystallized from ethanol. [1440] [1441] b) Preparation of 6 - [[3- [(3,4-dimethylphenyl) amino] -4,6-dinitrophenyl] oxy] hexanoic acid methyl ester [1442] 5 g of 3 - [(3,4-dimethylphenyl) amino] -4,6-dinitrophenol was O-alkylated with 6-bromohexanoic acid methyl ester at 70 <0> C in a similar manner to General Procedure Guide 8. [1443] 1 H-NMR (CDC1 3) δ = 1.45-1.88 ppm m (6H); 2.30 s (6 H); 2.33 t (J = 7.5 Hz, 2H) 3.68 s (3H); 3.88 t (J = 7.1 Hz, 2H); 6.41; s (1H); 7.00-7.08 m (2H); 7.25 d (J = 8 Hz, 1H); 9.03 s (1H); 9.89 s (wide) (1H) [1444] c) Preparation of 6 - [(5-amino-1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid methyl ester [1445] 2.45 g of 6 - [[3 - [(3,4-dimethylphenyl) amino] -4,6-dinitrophenyl] oxy] hexanoic acid methyl ester was hydrogenated in methanol according to general method 1. 500 mg of the crude product was reacted with benzimidated hydrochloride according to General Method 4. Unlike in General Method 4, after recovery in solvent, the crude product is purified by aq. It was not washed with hydrochloric acid. [1446] [1447] Example 209 [1448] Amino] -1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoate ester [1449] Oxy] hexanoic acid methyl ester was reacted with 4-chlorobenzenesulfonic acid chloride and general (2-amino-1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol- The method was reacted according to Guideline 13. [1450] Flash point 186-191 ℃ [1451] Example 210 [1452] (4-methoxyphenyl) -1H-benzimidazol-6-yl) oxy] hexanoic acid methyl ester [1453] Was prepared analogously to 6 - [(5-amino-1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl) oxy] -hexanoic acid methyl ester. [1454] MS (EI): 477 (molecular ion peak) [1455] Example 211 [1456] Phenyl] -1H-benzimidazol-6-yl) oxy] -hexanoic acid methyl ester < EMI ID = [1457] Was prepared analogously to 6 - [(5-amino-1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl) oxy] -hexanoic acid methyl ester. [1458] MS (EI): 489 (molecular ion peak) [1459] Example 212 [1460] (4-methoxyphenyl) -1H-benzimidazol-6-yl] -6-methyl-2- Oxy] hexanoic acid methyl ester [1461] (4-methoxy-phenyl) -1H-benzimidazol-6-yl) oxy] hexanoic acid methyl ester was reacted with 6 - [(5- amino- To react with 4-chlorobenzenesulfonic chloride. [1462] Flash point 180-182 ° C [1463] Example 213 [1464] (4-methoxyphenyl) -1H-benzimidazol-6-yl] -6- [ Oxy] hexanoic acid methyl ester [1465] (4-methoxyphenyl) -1H-benzimidazol-6-yl) oxy] hexanoic acid methyl ester was reacted with 6 - ((5-amino- To react with 4-chlorobenzenesulfonic chloride. [1466] Flash point 169-171 ℃ [1467] Example 214 [1468] 4 - [(5-amino-1- (4-methoxyphenyl) -2-phenyl-1H-benzimidazol-6-yl) oxy] butanoic acid methyl ester [1469] Was prepared analogously to 6 - [(5-amino-1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl) oxy] -hexanoic acid methyl ester. [1470] [1471] Example 215 [1472] (4-methoxyphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] butanoic acid methyl ester [1473] (4-methoxyphenyl) -2-phenyl-1H-benzimidazol-6-yl) oxy] butanoic acid methyl ester was reacted with 4-chlorobenzenesulfur ≪ / RTI > [1474] MS (EI): 605 (molecular ion peak) [1475] Example 216 [1476] 5 - [(5-amino-1- (4-methoxyphenyl) -2-phenyl-1H-benzimidazol-6-yl) oxy] pentanoic acid methyl ester [1477] Was prepared analogously to 6 - [(5-amino-1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl) oxy] -hexanoic acid methyl ester. [1478] [1479] Example 217 [1480] 2-phenyl-1H-benzimidazol-6-yl] oxy] pentanoic acid methyl ester [1481] (4-methoxyphenyl) -2-phenyl-1H-benzimidazol-6-yl) oxy] pentanoic acid methyl ester was reacted with 4-chlorobenzene ≪ / RTI > [1482] MS (EI): 619 (molecular ion peak) [1483] Example 218 [1484] 6 - [(5-amino-1- (4-methoxyphenyl) -2-phenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid methyl ester [1485] Was prepared analogously to 6 - [(5-amino-1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl) oxy] -hexanoic acid methyl ester. [1486] Flash point 129-131 ° C [1487] Example 219 [1488] Methyl] -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoate was obtained in the same manner as in [ ester [1489] 6-yl) oxy] hexanoic acid methyl ester was reacted with 4-chlorobenzene according to general procedure Directive 13 to yield the title compound as a white solid, MS (ISP): m / Sulfonic acid chloride. [1490] Flash point l68-170 ℃ [1491] Example 220 [1492] 6 - [[5 - [[(4-chlorophenyl) sulfonylamino] -1- (4- methoxyphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid [1493] Were obtained by reacting according to the General Methods Guide 9. [1494] Flash point 181-182 ℃ [1495] Example 221 [1496] 6 - [(5-amino-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid methyl ester [1497] Was prepared analogously to 6 - [(5-amino-1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl) oxy] -hexanoic acid methyl ester. [1498] Flash point 105-107 ℃ [1499] Example 222 [1500] Amino] -1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1501] (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid methyl ester was reacted with 4-chlorobenzenesulfonic acid chlor Reed was reacted. [1502] Flash point 189-191 ℃ [1503] Example 223 [1504] Amino] -1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid [1505] Were reacted according to the General Method Guide 9. [1506] Flash point 102-105 ℃ [1507] Example 224 [1508] 5 - [(5-amino-1,2-diphenyl-1H-benzimidazol-6-yl) oxy] pentanoic acid methyl ester [1509] Was prepared analogously to 6 - [(5-amino-1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl) oxy] -hexanoic acid methyl ester. [1510] [1511] Example 225 [1512] 5 - [[5 - [[(4-chlorophenyl) sulfonyl] amino] -1,2-diphenyl-1H-benzimidazol-6-yl] oxy] pentanoic acid methyl ester [1513] 5 - [(5-amino-1,2-diphenyl-1H-benzimidazol-6-yl) oxy] pentanoic acid methyl ester was reacted with 4-chlorobenzenesulfonic chloride according to general procedure directive 13. [1514] Flash point 157-161 ° C [1515] Example 226 [1516] 5 - [[5 - [[(4-chlorophenyl) sulfonyl] amino] -1,2-diphenyl-1H-benzimidazol-6-yl] oxy] pentanoic acid [1517] Were obtained by reacting in accordance with General Methods Guide 9. [1518] Flash point 236-242 ℃ [1519] Example 227 [1520] Methyl] -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoate was obtained in the same manner as in Reference Example 1, except that 6 - [[5 - [[(4- fluorophenyl) sulfonyl] amino] ester [1521] 6-yl) oxy] hexanoic acid methyl ester was reacted with 4-fluorobenzene according to general procedure Directive 13 to yield the title compound as a white solid, MS (ISP): m / Sulfonic acid chloride. [1522] MS (EI): 617 (molecular ion peak) [1523] Example 228 [1524] (4-methoxy-phenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy ] Hexanoic acid methyl ester [1525] 6-yl) oxy] hexanoic acid methyl ester was reacted with 4- (4-methoxyphenyl) -2-phenyl-1H-benzimidazol- Fluoromethyl) benzenesulfonyl chloride. ≪ / RTI > [1526] MS (EI): 668 (molecular ion peak) [1527] Example 229 [1528] 2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid < EMI ID = [1529] Were prepared according to the General Method Guide 9. [1530] Flash point 190-192 ° C [1531] Example 230 [1532] Methyl] amino] -1- (4-methoxyphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoate ester [1533] 2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid Methyl ester was dissolved in 3 ml of tetrahydrofuran and 10 mg of sodium hydride was added at 0 DEG C. After stirring for 30 minutes, 50 mu l of methyl iodide was added dropwise and the mixture was further stirred for 60 minutes at 0 DEG C. It was stirred with saturated ammonium Mixed with chloride solution, extracted three times with ethyl acetate, the organic phase was washed with water, dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel. [1534] Flash point 178-180 ℃ [1535] Example 231 [1536] [(4-chlorophenyl) sulfonyl] [1,2-diphenyl-1H-benzimidazol-5-yl] amino] acetic acid methyl ester [1537] 100 mg of 4-chloro-N- (1,2-diphenyl-1H-benzimidazol-5-yl) benzenesulfonamide was dispersed in 0.5 ml of N, N-dimethylformamide and 8 mg of sodium hydride And stirred at 20 [deg.] C for 30 minutes. 50 mg of bromoacetic acid methyl ester was added, stirred for 15 hours, mixed with water, extracted three times with ethyl acetate and the extract was dried over sodium sulfate and concentrated by evaporation in vacuo. The residue was chromatographed on silica gel. [1538] [1539] Example 232 [1540] [(4-chlorophenyl) sulfonyl] [1,2-diphenyl-1H-benzimidazol-5-yl] amino] [1541] Were prepared according to the General Method Guide 9. [1542] Flash point 248 ℃ [1543] Example 233 [1544] 4 - [[(4-chlorophenyl) sulfonyl] (1,2-diphenyl-1H-benzimidazol-5-yl] amino] butanoic acid methyl ester [1545] 100 mg of 4-chloro-N- (1,2-diphenyl-1H-benzimidazol-5-yl) benzenesulfonamide was dispersed in 0.5 ml of N, N-dimethylformamide and 6 mg of sodium hydride Followed by stirring at 20 ° C for 30 minutes. 56 mg of 4-bromobutyric acid methyl ester was added and it was stirred for 15 hours. After mixing with water, it was extracted three times with ethyl acetate, and the extract was dried over sodium sulfate and concentrated by evaporation in vacuo. The residue was digested with diisopropyl ether. [1546] Flash point 54-58 ℃ [1547] Example 234 [1548] 4 - [[(4-chlorophenyl) sulfonyl] [1,2-diphenyl-1H-benzimidazol-5- yl] amino] [1549] Were prepared according to the General Method Guide 9. [1550] Flash point 249-254 ℃ [1551] Example 235 [1552] 5 - [[(4-chlorophenyl) sulfonyl] [112-diphenyl-1H-benzimidazol-5-yl] amino] pentanoic acid methyl ester [1553] 100 mg of 4-chloro-N- (1,2-diphenyl-1H-benzimidazol-5-yl) benzenesulfonamide was dispersed in 0.5 ml of N, N-dimethylformamide and 8 mg of sodium hydride And stirred at 20 [deg.] C for 30 minutes. 60 mg of 5-bromopentanoic acid methyl ester was added and it was stirred for 15 hours. After mixing with water, it was extracted three times with ethyl acetate, and the extract was dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel. [1554] [1555] Example 236 [1556] 5 - [[(4-chlorophenyl) sulfonyl] [1,2-diphenyl-1H-benzimidazol- [1557] Were prepared according to the General Method Guide 9. [1558] Flash point 123-127 ℃ [1559] Example 237 [1560] 6 - [[(4-chlorophenyl) sulfonyl] [1,2-diphenyl-1H-benzimidazol-5-yl] amino] hexanoic acid methyl ester [1561] 6 - [[1,2-diphenyl-1H-benzimidazol-5-yl] amino] hexanoic acid methyl ester was reacted with 4-chlorobenzenesulfonic chloride according to general procedure directive 13. [1562] MS (EI): 588 (molecular ion peak) [1563] Example 238 [1564] 7 - [[(4-chlorophenyl) sulfonyl] [1,2-diphenyl-1H-benzimidazol-5-yl] amino] heptanoic acid methyl ester [1565] 100 mg of 4-chloro-N- (1,2-diphenyl-1H-benzimidazol-5-yl) benzenesulfonamide was dispersed in 0.5 ml of N, N-dimethylformamide and 8 mg of sodium hydride , And the mixture was stirred at 20 DEG C for 30 minutes. 70 mg of 7-bromoheptanoic acid methyl ester was added, stirred for 15 hours, mixed with water and extracted three times with ethyl acetate, and the extract was dried over sodium sulfate and concentrated by evaporation in vacuo. The residue was chromatographed on silica gel. [1566] [1567] Example 239 [1568] 7 - [[(4-chlorophenyl) sulfonyl] [1,2-diphenyl-1H-benzimidazol-5-yl] amino] heptanoic acid [1569] Were prepared according to the General Method Guide 9. [1570] Flash point 172-178 ° C [1571] Example 240 [1572] N- (1,2-diphenyl-1H-benzimidazol-5-yl) -4-fluorobenzenesulfonamide [1573] 5-Amino-l, 2-diphenyl-lH-benzimidazole was reacted with 4-fluorobenzenesulfonic chloride according to general procedure directive 13. [1574] Flash point 209-214 ℃ [1575] Example 241 [1576] 6 - [[(4-fluorophenyl) sulfonyl] [1,2-diphenyl-1H-benzimidazol-5-yl] amino] hexanoic acid methyl ester [1577] 150 mg of N- (1,2-diphenyl-1H-benzimidazol-5-yl) -4-fluorobenzenesulfonamide was dispersed in 0.5 ml of N, N-dimethylformamide, Was mixed with sodium hydride and stirred for 30 min at 20 < 0 > C. 98 mg of 6-bromohexanoic acid methyl ester was added, stirred for 15 hours, mixed with water, extracted three times with ethyl acetate, the extract was dried over sodium sulfate and concentrated by evaporation in vacuo. The residue was chromatographed on silica gel. [1578] Flash point 128-134 ° C [1579] Example 242 [1580] Amino] hexanoic acid < RTI ID = 0.0 > (3-fluorophenyl) [1581] Were prepared according to the General Method Guide 9. [1582] Flash point 200-210 ℃ [1583] Example 243 [1584] Phenyl] sulfonyl] [1,2-diphenyl-1H-benzimidazol-5-yl] -amino} hexanoic acid methyl ester [1585] 150 mg of 4- (trifluoromethyl) -N- (1,2-diphenyl-1H-benzimidazol-5-yl) benzenesulfonamide was dispersed in 0.5 ml of N, N-dimethylformamide, Mixed with 11 mg of sodium hydride, and then stirred at 20 DEG C for 30 minutes. 88 mg of 6-bromohexanoic acid methyl ester was added, stirred for 15 hours, then mixed with water, extracted three times with ethyl acetate, the extract was dried over sodium sulfate and concentrated by evaporation in vacuo. The residue was digested with diisopropyl ether. [1586] Flash point 159-161 ° C [1587] Example 244 [1588] Phenyl] sulfonyl] [1,2-diphenyl-1H-benzimidazol-5-yl] -amino} hexanoic acid [1589] Were prepared according to the General Method Guide 9. [1590] Flash point 224-230 ℃ [1591] Example 245 [1592] 4-Chloro-N- [1- (4-methoxyphenyl) -2-phenyl-1H-benzimidazol-5-yl] benzenesulfonamide [1593] a) (2,4-Dinitrophenyl) (4-methoxyphenyl) amine [1594] 1.43 g of 4- (2,4-dinitroanilino) phenol, 500 mg of potassium carbonate and 0.32 ml of methyl iodide were stirred in 5 ml of N, N-dimethylformamide for 2 days at 20 ° C . The mixture was poured into water and extracted three times with ethyl acetate, then the extract was dried over sodium sulfate and concentrated in vacuo to dryness. The residue was chromatographed on silica gel. [1595] Flash point 117-127 ℃ [1596] b) 5-Amino-1- (4-methoxy-phenyl) -2-phenyl-1H-benzimidazole [1597] (2,4-dinitrophenyl) (4-methoxyphenyl) amine was hydrogenated according to general method 1. The crude product was cyclized with trimethyl orthobenzoate as a benzimidazole derivative according to General Method 3. [1598] [1599] c) 4-Chloro-N- [1- (4-methoxyphenyl) -2-phenyl-lH-benzimidazol- 5-yl] benzenesulfonamide [1600] 5-Amino-1- (4-methoxyphenyl) -2-phenyl-1H-benzimidazole was reacted with 4-chlorobenzenesulfonic chloride according to general methodology, Scheme 13. [1601] Flash point 238-24 ℃ [1602] Example 246 [1603] Phenyl] -1H-benzimidazol-5-yl] amino] hexanoic acid methyl ester (Compound [1604] 75 mg of 4-chloro-N- [1- (4-methoxy-phenyl) -2-phenyl-1H-benzimidazol-5-yl] benzenesulfonamide was dissolved in 0.5 ml of N, N-dimethylformamide Dispersed, mixed with 6 mg of sodium hydride, and stirred at 20 DEG C for 30 minutes. 44 mg of 6-bromohexanoic acid methyl ester was added and stirred for 15 hours. After mixing with water, it was extracted three times with ethyl acetate, and the extract was dried over sodium sulfate and concentrated by evaporation in vacuo. The residue was chromatographed on silica gel. [1605] MS (EI): 617 (molecular ion peak) [1606] Example 247 [1607] 2-phenyl-1H-benzimidazol-5-yl] amino] hexanoic acid < [1608] Were prepared according to the General Method Guide 9. [1609] Flash point 205-208 ℃ [1610] Example 248 [1611] 2,2-dimethyl-6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide [1612] a) 2,2-Dimethyl-6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanonitrile [1613] Was obtained by reacting 1,2-diphenyl-6-hydroxy-1H-benzimidazole and 6-bromo-1,1-dimethylhexanonitrile according to General Method Guide 8. [1614] Flash point 115-118 ℃. [1615] b) 2,2-Di-methyl-6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide [1616] 500 mg of 2,2-dimethyl-6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanonitrile was refluxed in 5 ml of 80% sulfuric acid for 2 hours. After cooling, it was carefully added to ice water and the pH was adjusted to 8 with sodium hydroxide solution. It was extracted three times with ethyl acetate, and the extract was dried over sodium sulfate, which was concentrated by evaporation in vacuo. The residue was chromatographed on silica gel. [1617] Flash point 115-118 ℃ [1618] Example 249 [1619] 8 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] octanoic acid methyl ester [1620] Was obtained by reacting 1,2-diphenyl-6-hydroxy-1H-benzimidazole and 8-bromooxanic acid methyl ester according to General Method Guide 8. [1621] Flash point 92-95 ℃ [1622] Example 250 [1623] 8 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] octanoic acid [1624] Were prepared according to the General Method Guide 9. [1625] Flash point 136-140 ° C [1626] Example 251 [1627] 6 - [[1- (indan-5-yl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1628] Phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester. [1629] Flash point 81-85 ℃ [1630] Example 252 [1631] 6 - [[1- (indan-5-yl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid [1632] Were prepared according to the General Method Guide 9. [1633] Flash point 176-180 ℃ [1634] Example 253 [1635] 7 - [[1- (indan-5-yl) -2-phenyl-1H-benzimidazol-6-yl] oxy] heptanoic acid methyl ester [1636] Was prepared in analogy to 6 - [[l- (3,4-dimethylphenyl) -2-phenyll-benzimidazol-6-yl] oxy] hexanoic acid methyl ester. [1637] Flash point 92-98 ℃ [1638] Example 254 [1639] 7 - [[1- (indan-5-yl) -2-phenyl-1H-benzimidazol-6-yl] oxy] heptanoic acid [1640] Were prepared according to the General Method Guide 9. [1641] Flash point 175-173 ° C [1642] Example 255 [1643] 6 - [[1- (3-fluorophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1644] Was prepared in analogy to 6 - [[l- (3,4-dimethylphenyl) -2-phenyll-benzimidazol-6-yl] oxy] hexanoic acid methyl ester. [1645] Flash point 104 - 106 ° C [1646] Example 256 [1647] 6 - [[1- (3-fluorophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid [1648] Were prepared according to the General Method Guide 9. [1649] Flash point 149-151 ℃ [1650] Example 257 [1651] 6 - [[2- (4-nitrophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1652] a) 6-Methoxy-2- (4-nitrophenyl) -1-phenyl-1H-benzimidazole [1653] 200 mg of 4-methoxy-N 2 -phenyl-o-phenylenediamine was dissolved in 5 ml of N, N-dimethylformamide and mixed with 346 mg of EEDQ and 234 mg of 4-nitrobenzoic acid. The mixture was stirred at 1000C for 5 hours. After cooling, the mixture was mixed with water, the precipitate was inhaled, and purified by column chromatography. 6N hydrochloric acid and refluxed for 2 hours. After cooling, the solution was added dropwise to a saturated potassium bicarbonate solution. The precipitate was aspirated and dried. [1654] Flash point 189-191 ℃ [1655] b) 6-Hydroxy-2- (4-nitrophenyl) -1-phenyl-1H-benzimidazole [1656] Were reacted according to the General Methods Guide 6. [1657] [1658] c) Preparation of 6 - [[2- (4-nitrophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1659] Were reacted according to the general method guidance 8. [1660] [1661] Example 258 [1662] 6 - [[2- (4-nitrophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid [1663] Were prepared according to the General Method Guide 9. [1664] Flash point 181-186 ℃ [1665] Example 259 [1666] 6 - [[l-phenyl-2- (3-pyridinyl) -lH-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1667] Was prepared analogously to 6 - [[l-phenyl-2- (4-pyridinyl) -lH-benzimidazol-6-yl] oxy] hexanoic acid methyl ester. [1668] Flash point 159-160 ℃ [1669] Example 260 [1670] N- (cyclopropylmethoxy) -6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide [1671] Was prepared in accordance with General Methods Directive 18. [1672] MS (EI): 469 (molecular ion peak) [1673] Example 261 [1674] N-isobutoxy-6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide [1675] Was prepared in accordance with General Methods Directive 18. [1676] MS (EI): 471 (molecular ion peak) [1677] Example 262 [1678] N- (phenylmethoxy) -6- [2-phenyl-1- (3,4,5-trimethoxyphenyl) -1H-benzimidazol-6-yl) oxy] [1679] A solution of 50 mg of 6- [2-phenyl-1- (3,4,5-trimethoxyphenyl) -1H-benzimidazol-6-yl) oxy] hexanoic acid in 1 ml of tetrahydrofuran was treated with 1 ml of Was added to a solution consisting of 17 mg of carbonyldiimidazole in tetrahydrofuran. It was stirred at 20 [deg.] C for 30 minutes and refluxed for 30 minutes. At 20 [deg.] C, 16 mg of O-benzylhydroxylamine hydrochloride was added and it was stirred for 20 hours. Ethyl acetate was added for recovery and extracted with 2N hydrochloric acid and saturated sodium bicarbonate solution. It was dried over sodium sulfate and evaporated in vacuo. The residue was purified by chromatography on silica gel. [1680] Flash point 145-148 ° C [1681] Example 263 [1682] (Cyclopropylmethoxy) -6- [2-phenyl-1- (3,4,5-trimethoxyphenyl) -1H-benzimidazol-6-yl) oxy] hexanamide [1683] Was prepared analogously to N- (phenylmethoxy) -6- [2-phenyl-1- (3,4,5-trimethoxyphenyl) -1H-benzimidazol-6-yl) oxy] hexanamide . [1684] MS (EI): 559 (molecular ion peak) [1685] Example 264 [1686] N-isobutoxy-6- [2-phenyl-1- (3,4,5-trimethoxy-phenyl) -1H-benzimidazol-6-yl) oxy] hexanamide [1687] Was prepared analogously to N- (phenylmethoxy) -6- [2-phenyl-1- (3,4,5-trimethoxyphenyl) -1H-benzimidazol-6-yl) oxy] hexanamide . [1688] [1689] Example 265 [1690] N-isopropyl-6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide [1691] Was prepared in accordance with General Methods Guide 17. [1692] Flash point 107-112 ° C [1693] Example 266 [1694] N, N-dimethyl-6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide [1695] Was prepared in accordance with General Methods Guide 17. [1696] Flash point 83-88 ℃ [1697] Example 267 [1698] 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] -1-pyrrolidin- 1 -ylhexan- [1699] Was prepared in accordance with General Methods Guide 17. [1700] Flash point 84-88 ℃ [1701] Example 268 [1702] N- (2-methoxyethyl) -6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide [1703] Was prepared in accordance with General Methods Guide 17. [1704] Flash point 63-68 ℃ [1705] Example 269 [1706] N- (3-methoxypropyl) -6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide [1707] Was prepared in accordance with General Methods Directive 18. [1708] Flash point 84-91 ℃ [1709] Example 270 [1710] N-isobutyl-6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide [1711] Was prepared in accordance with General Methods Guide 17. [1712] [1713] Example 271 [1714] N - [(2,2-dimethylamino) ethyl] -N-methyl-6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) -oxy] hexanamide [1715] Was prepared in accordance with General Methods Guide 17. [1716] [1717] Example 272 [1718] N- (2-methoxyethyl) -N-methyl-6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide [1719] Was prepared in accordance with General Methods Guide 17. [1720] [1721] Example 273 [1722] 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] -1-morpholin-1-ylhexan- [1723] Was prepared in accordance with General Methods Guide 17. [1724] [1725] Example 274 [1726] N, N-di (2-methoxyethyl) -6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide [1727] Was prepared in accordance with General Methods Directive 18. [1728] Flash point 88-98 ℃ [1729] Example 275 [1730] N-isopentyl-6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide [1731] Was prepared in accordance with General Methods Directive 18. [1732] Flash point 127-129 ℃ [1733] Example 276 [1734] 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide [1735] Was prepared in accordance with General Methods Directive 18. [1736] Flash point 120-124 ° C [1737] Example 277 [1738] 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide [1739] Was prepared in accordance with General Methods Directive 18. [1740] Flash point 154 ℃ [1741] Example 278 [1742] 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] -1- piperidin- 1 -ylhexan- [1743] Was prepared in accordance with General Methods Directive 18. [1744] Flash point 93-98 ℃ [1745] Example 279 [1746] [6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] -1-hexanoyl] piperidine- [1747] Was prepared in accordance with General Methods Guide 17. [1748] Flash point 177-178 ℃ [1749] Example 280 [1750] [[6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] -1-hexanoyl] methylamino] -acetic acid ethyl ester [1751] Was prepared in accordance with General Methods Guide 17. [1752] [1753] Example 281 [1754] 4 - [[6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] -1-hexanoyl] piperazine-1-carboxylic acid ethyl ester [1755] Was prepared in accordance with General Methods Guide 17. [1756] [1757] Example 282 [1758] N-isopropyl-6- [[1- (3,4-di-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanamide [1759] Was prepared in accordance with General Methods Directive 18. [1760] MS (EI): 469 (molecular ion peak) [1761] Example 283 [1762] N, N-dimethyl-6- [[1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] [1763] Was prepared in accordance with General Methods Directive 18. [1764] MS (EI): 455 (molecular ion peak) [1765] Example 284 [1766] N, N-diethyl-6- [[1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazole 6-yl] oxy] hexanamide [1767] Was prepared in accordance with General Methods Directive 18. [1768] MS (EI): 483 (molecular ion peak) [1769] Example 285 [1770] N-isobutyl-6 - [[1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanamide [1771] Was prepared in accordance with General Methods Directive 18. [1772] [1773] Example 286 [1774] Cyclopropyl-6- [[1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] [1775] Was prepared in accordance with General Methods Directive 18. [1776] MS (EI): 467 (molecular ion peak) [1777] Example 287 [1778] N-cyclobutyl-6 - [[1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] -oxy] hexanamide [1779] Was prepared in accordance with General Methods Directive 18. [1780] [1781] Example 288 [1782] N-tert-butyl-6 - [[1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanamide [1783] Was prepared in accordance with General Methods Directive 18. [1784] [1785] Example 289 [1786] 6-yl] oxy] l- (2-methoxy-methyl) pyrrolidin-l- -Hexan-1-one [1787] Was prepared in accordance with General Methods Directive 18. [1788] MS (EI): 467 (molecular ion peak) [1789] Example 290 [1790] 6 - [[1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanamide [1791] Was prepared in accordance with General Methods Directive 18. [1792] [1793] Example 291 [1794] 2-ylethyl) -6 - [[1- (3,4-di-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanamide [1795] Was prepared in accordance with General Methods Directive 18. [1796] [1797] Example 292 [1798] N, N-di-methyl-6- [[2- (4-nitrophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanamide [1799] Was prepared in accordance with General Methods Directive 18. [1800] [1801] Example 293 [1802] N-isopropyl-6 - [[2- (4-nitrophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanamide [1803] Was prepared in accordance with General Methods Directive 18. [1804] Flash point 162-165 ° C [1805] Example 294 [1806] N-isopentyl-6- [[2- (4-nitrophenyl) -phenyl-1 H-benzimidazol-6-yl] oxy] hexanamide [1807] Was prepared in accordance with General Methods Directive 18. [1808] Flash point 148-154 ℃ [1809] Example 295 [1810] -6- [[2- (4-nitrophenyl) -1-phenyl-1H-benzimidazol-6-yl] -oxy] hexanamide [1811] Was prepared in accordance with General Methods Directive 18. [1812] Flash point 104-110 ° C [1813] Example 296 [1814] (3-methoxypropyl) -6 - [[1- (indan-5-yl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanamide [1815] Was prepared in accordance with General Methods Directive 18. [1816] [1817] Example 297 [1818] 6 - [[1- (4-methylphenyl) -2- (3-pyridyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1819] Was obtained by reacting 6 - [[4-amino-3 - ((4-methylphenyl) amino) phenyl] -oxy] hexanoic acid methyl ester and 3-pyridylcarbaldehyde according to General Method Guide 16. [1820] MS (EI): 429 (molecular ion peak) [1821] Example 298 [1822] 6 - [[1- (4-methylphenyl) -2- (4-pyridyl) -1H-benzimidazol-6-yl) oxy] hexanoic acid methyl ester [1823] Was obtained by reacting 6 - [[4-amino-3 - ((4-methylphenyl) amino) phenyl] -oxy] hexanoic acid methyl ester and 4-pyridylcarbaldehyde according to General Method Guide 16. [1824] MS (EI): 429 (molecular ion peak) [1825] Example 299 [1826] 6 - [[1- (4-methylphenyl) -2- (2-thienyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1827] Was obtained by reacting 6 - [[4-amino-3 - ((4-methylphenyl) amino) phenyl] -oxy] hexanoic acid methyl ester and 2-thienylcarbaldehyde according to General Method Guide 16. [1828] MS (EI): 434 (molecular ion peak) [1829] Example 300 [1830] 6 - [[1- (4-methylphenyl) -2- (3-thienyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1831] Was obtained by reacting 6 - [[4-amino-3 - ((4-methylphenyl) amino) phenyl] -oxy] hexanoic acid methyl ester and 3-thienylcarbaldehyde according to General Method Guide 16. [1832] MS (EI): 434 (molecular ion peak) [1833] Example 301 [1834] 6 - [[2- (3-indolyl) -1- (4-methylphenyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1835] Was obtained by reacting 6 - [[4-amino-3 - ((4-methylphenyl) amino) phenyl] -oxy] hexanoic acid methyl ester and 3-indolylcarbaldehyde according to General Method Guide 16. [1836] MS (EI): 467 (molecular ion peak) [1837] Example 302 [1838] 6 - [[1- (4-methylphenyl) -2- (2-furyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1839] Was obtained by reacting 6 - [[4-amino-3 - ((4-methylphenyl) amino) phenyl] -oxy] hexanoic acid methyl ester and 2-furylcarbaldehyde according to General Method Guide 16. [1840] MS (EI): 418 (molecular ion peak) [1841] Example 303 [1842] 6 - [[1- (4-methylphenyl) -2- (3-furyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1843] Was obtained by reacting 6 - [[4-amino-3 - ((4-methylphenyl) amino) phenyl] -oxy] hexanoate and 3-furylcarbaldehyde according to General Methodology, [1844] MS (EI): 418 (molecular ion peak) [1845] Example 304 [1846] 6 - [[1- (4-methylphenyl) -2- (5-methyl-2-thienyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1847] Is reacted with 6 - [[4-amino-3 - ((4-methylphenyl) amino) phenyl] -oxy] hexanoic acid methyl ester and 5-methyl-2-thienyl-carbaldehyde according to general procedure directive 16 . [1848] MS (EI): 448 (molecular ion peak) [1849] Example 305 [1850] 6 - [[1- (4-methylphenyl) -2- (4-bromo-2- thienyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1851] Is reacted with 6 - [[4-amino-3- ((4-methylphenyl) amino) phenyl] -oxy] hexanoic acid methyl ester and 4-bromo-2-thienylcarbaldehyde according to general procedure directive 16 . [1852] MS (EI) - 512/514 (molecular ion peak) [1853] Example 306 [1854] 6 - [[1- (4-methylphenyl) -2- (3-methyl-2-thienyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester [1855] Was obtained by reacting 6 - [[4-amino-3- ((4-methylphenyl) amino) phenyl] -oxy] hexanoic acid methyl ester and 3-methyl- . [1856] MS (EI): 448 (molecular ion peak) [1857] Example 307 [1858] Inhibition of microglial activation [1859] For in vitro production of A [beta] -activated microglia, primary rat microglia were incubated with synthetic A [beta] -peptide: [1860] To simulate A [beta] deposits, synthetic A [beta] peptides were dried in 96-well tissue culture plates. H 2 0 and diluted so that 2 ㎎ / ㎖ peptide stock solution in water, a 1:50. To coat the 96-well plate, 30 μl of this diluted peptide solution per well was used and dried overnight at room temperature. [1861] Primary rat microglia were recovered by mixed cultured cell culture obtained from P3 rat brain. In the preparation of mixed germ cell cultures, the brain was obtained from 3 days old rats and the meninges were removed. Cells were isolated by trypsinization (0.25% trypsin solution, 37 < 0 > C for 15 min). Undigested tissue fragments were separated into 40 mu m nylon sieves, and then the separated cells were centrifuged (800 rpm / 10 min). The cell pellet was resuspended in the medium and transferred to a 100 ml tissue culture flask (one brain per tissue culture flask). The cells were cultured in Dulbecco's modified Eagle's medium (DMEM, with glutamine) supplemented with penicillin (50 U / ml), streptomycin (40 μg / ml) and 10% (v / v) fetal bovine serum ℃ and it was achieved in 5% CO 2. During the incubation an adhesive cellular film consisting mainly of astrocytes was generated. Above this, microglia grew into nonadherent or weak adhesive cells and collected via shaking incubation (420 rpm, 1 hour). [1862] In order to enable fine glial by Aβ- peptide, Aβ- per hole in the coated tissue culture plates 2.5x10 4 of the fine glial cells was grown, 37 ℃ and penicillin over a period of 7 days at 5% CO 2 (50U / ㎖ ) , DMEM supplemented with streptomycin (40 [mu] g / ml) and 10% (v / v) fetal calf serum (FCS) (with glutamine). On day 5, the compounds according to the invention were added at various concentrations (0.1, 0.3, 1.3 and 10 mu m). [1863] To quantify the reactivity of microglia, MTS (3 (4,5-dimethylthiazol-2-yl) -5- (3- carboxymethoxy- phenyl) -2- (sulfophenyl) Metabolic activity was measured by reduction of the enzyme activity (2H-tetrazolium) (Owen's reagent; Baltrop, JA et al., Bioorg. & Med. Chem. Lett. 1, 6111 (1991)). The inhibition rate is based on the control group treated only with DMSO. The compounds according to the invention inhibited microglia activation. [1864] Example 308 [1865] Cerebral infarction in rats (MCAO model) [1866] Compounds according to the present invention were tested for in vivo activity in a cerebral ischemia (stroke) animal model, the MCAO (permanent middle cerebral artery occlusion) model. Unilateral occlusion of the MCA leads to cerebral infarction due to lack of oxygen and nutrients in the affected area of the brain. The consequence of this deficiency is marked cell degeneration and the subsequent strong microcytic cell activation. Activation of these microcytes is only reached in a few days, and lasts for several weeks. To test the substance, the compounds according to the invention were administered intraperitoneally after 1-6 days of occlusion. On day 7, the animals were perfused and killed. The degree of microglial activation was measured by modified immunohistochemical method. The vibratom portion of the fixed brain was incubated with the antibody. Wherein said portion detects MHCII complex or CR3 complement receptor on activated microglia. Quantification of primary antibody binding was done by an enzyme binding detection system. Treatment with the compounds according to the present invention greatly reduced microglia activation in the cerebral hemisphere due to cerebral infarction. The reduction rate was more than 20%. [1867] Example 309: [1868] Activation of macrophages [1869] To test the material for macrophages / monocytes, LPS-activated THP-1 cells were used. For this purpose, 2.5 x 106 cells / ml were grown in RPMI medium (RPMI 1640 + 10% FCS). The compounds according to the invention were added at a concentration of 5 [mu] M and pre-incubated for 30 minutes. Cell stimulation was carried out at 37 占 폚 overnight with 1 占 퐂 / ml of LPS. Then, the medium was collected and the amount of TNFA was determined quantitatively. Treatment of the cells with the material according to the invention showed a decrease in the amount of TNFA over 30%.
权利要求:
Claims (24) [1" claim-type="Currently amended] ≪ / RTI > (I) (here, R 1 is a monocyclic or bicyclic C 6-12 aryl group or a monocyclic or bicyclic 5- to 10-membered heteroaryl group having 1 to 4 heteroatoms selected from the group consisting of N, S, or O (the above mentioned aryl or heteroaryl groups, independently of each other, may be substituted with substituent to three: F, Cl, Br, I, C (NH) NH 2, C (NH) NHR 4, C (NH ) NR 4 R 4 ', C (NR 4) NH 2, C (NR 4) NHR 4', C (NR 4) NR 4 R 4 ', XOH, XOR 4, XOCOR 4, XOCONHR 4, XOCOOR 4, XCOR 4, XC (NOH) R 4 , XC (NOR 4) R 4 ', XC (NO (COR 4)) R 4', XCN, XCOOH, XCOOR 4, XCONH 2, XCONR 4 R 4 ', XCONHR 4, XCONHOH , XCONHOR 4, XCOSR 4, XSR 4, XSOR 4, XSO 2 R 4, S0 2 NH 2, S0 2 NHR 4, SO 2 NR 4 R 4 ', N0 2, XNH 2, XNHR 4, XNR 4 R 4' , XNHS0 2 R 4, XN ( SO 2 R 4) SO 2 R 4 ', XNR 4 SO 2 R 4', XNHCOR 4, XNHCOOR 4, XNHCONHR 4, tetrahydro-2,5-dioxide Sophie roll-yl , 2,5-dihydro-2,5-dioxopyrrol-1-yl, 2,7-dihydro-2,7-dioxane Isoindol-1-yl, R 4 (where the two substituents of R 1 each other if there at the ortho position, they together methane diyl bis oxy, ethane-1,2-diyl-bis-oxy, propane-1,3-diyl , Butane-1,4-diyl)), R 2 is a monocyclic or bicyclic C 6-10 aryl group or a monocyclic or bicyclic 5- to 10-membered heteroaryl having 1 to 4 heteroatoms selected from the group consisting of N, S or O group (the above-mentioned aryl or heteroaryl groups, independently of each other, may be substituted with substituent to three: F, Cl, Br, I, XOH, XOR 4, XOCOR 4, XOCONHR 4, XOCOOR 4, XCOR 4 , XC (NOH) R 4, XC (NOR 4) R 4 ', XC (NO (COR 4)) R 4', XCOOH, XCOOR 4, XCONH 2, XCONHR 4, XCONR 4 R 4 ', XCONHOH, XCONHOR 4 , XCOSR 4, XSR 4, XSOR 4, XSO 2 R 4, SO 2 NH 2, S0 2 NHR 4, SO 2 NR 4 R 4 ', N0 2, XNHR 4, XNR 4 R 4', XNHSO 2 R 4, XN (SO 2 R 4) SO 2 R 4 ', XNR 4 SO 2 R 4', tetrahydro-2,5-dioxide Sophie roll-yl, 2,5-dihydro-2,5-dioxide Sophie roll 1-yl, 2,7-dihydro-2,7-dioxo-isoindol If the 1-yl, R 4 (wherein, if the two substituents to each other ortho position of R 2, they together methane di Bis-oxy, ethane-1,2-diyl-bis-oxy, it means that can be connected to each other in such a manner as to form a propan-1,3-diyl, butane-1,4-diyl)), and R 3 is hydrogen, F, Cl, Br, I , XOH, XOR 4, XOCOR 4, XOCONHR 4, XOCOOR 4, XCOR 4, XC (NOH) R 4, XC (NOR 4) R 4 ', XC (NO ( COR 4 )) R 4 ' , XCN, XCOOH, XCOOR 4 , XCONH 2 , XCONHR 4 , XCONR 4 R 4' , XCONHOH, XCONHOR 4 , XCOSR 4 , XSR 4 , XSOR 4 , XSO 2 R 4 , SO 2 NH 2 , S0 2 NHR 4, S0 2 NR 4 R 4 ', N0 2, XNH 2, XNHR 4, XNR 4 R 4', XNHSO 2 R 4, XNR 4 SO 2 R 4 ', XN (SO 2 R 4) ( SO 2 R 4 '), XNHCOR 4, XNHCOOR 4, XNHCONHR 4, tetrahydro-2,5-dioxide Sophie roll-yl, 2,5-dihydro-2,5-dioxide Sophie roll-yl, 2,7-dihydro-2,7-dioxoisoindol-1-yl, or R 3 may be R 4 , wherein two substituents R 3 are If they are in ortho position to each other, they may be linked together in such a way that they form together methane di bisoxy, ethane-1,2-diyl bisoxy, propane-1,3-diyl, or butane-1,4-diyl) , R 4 and R 4 'are independently C 1-4 perfluoroalkyl, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, (C 1- each other 3 alkyl-C 3-7 cycloalkyl), C 1-3 alkyl-C 6-10 aryl, C 1-3 alkyl- (5-10 membered heteroaryl containing 1-4 N, S, or O atoms), C 6-10 aryl or 5 to 10 membered heteroaryl containing 1 to 4 N, S or 0 atoms wherein the aryl and heteroaryl groups are optionally substituted with F, Cl, Br, CH 3 , C 2 H 5 , NO 2 , OCH 3 , OC 2 H 5 , CF 3 .C 2 F 5 , or may be substituted by one or two substituents selected from the group consisting of an annelated methanediylbisoxy group or ethane- And one ring atom in the 5-membered cycloalkyl ring may be N or 0, and one or two ring atoms in the 6- or 7-membered cycloalkyl ring may be substituted by N and / or O And the ring nitrogen is optionally substituted with C Lt; / RTI > alkyl or Ci- 3 alkanoyl, R 5 and R 5 ' independently of one another are selected from the group consisting of C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl wherein one carbon atom is O, S, SO, SO 2 , NH, NC 1- 3 alkyl or NC 1-3 alkanoyl), C 3-7 cycloalkyl - C 0-3 alkyl wherein one ring atom of the 5 membered cycloalkyl ring may be N or 0, and 6 Or one or two ring atoms of the 7-membered cycloalkyl ring may be N and / or O, and the ring nitrogen may be optionally substituted with C 1-3 alkyl or C 1-3 alkanoyl), C 6 -10 aryl, or 5-10 membered heteroaryl containing 1 to 4 N, S or O heteroatoms wherein said alkyl, alkenyl and alkynyl chains are optionally substituted with one or more of the above-mentioned cycloalkyl, aryl or heteroaryl And all the above-mentioned alkyl and cycloalkyl radicals may be substituted by one of CF 3 , C 2 F 5 , OH, OC 1-3 alkyl, NH 2 , NHC 1-3 alkyl, NHC 1-3 alkanoyl, N (C 1-3 alkyl) 2 , N (C 1-3 alkyl) (C 1-3 alkanoyl), COOH, CONH 2 , COOC 1-3 alkyl, and all aryl and heteroaryl groups F, Cl, Br, CH 3 , C 2 H 5, N0 2, OCH 3, OC 2 H 5, CF 3, and may be substituted either by one or two substituents of the group from consisting of C 2 F 5, Or may be accompanied by an annelated methanediylbisoxy or ethane-1,2-diylbisoxy group, Or R 5 and R 5 'can contain, one more oxygen, nitrogen or sulfur atom together with the N atom and C 1-4 alkyl, C 1-4 alkoxy -C 2 O-alkyl, C 1-4 alkoxy- Form a 5- to 7-membered heterocyclic compound which may be substituted with carbonyl, aminocarbonyl or phenyl, A is C 1-10 alkanediyl, C 2-10 Al canned yl, C 2-10 alkyne diyl, (C O-5 alkanediyl -C 3-7 cycloalkyl alkanediyl -C 0-5 alkanediyl ) Wherein one ring atom of the five membered cycloalkyl ring may be N or O, one or two ring atoms of the 6 or 7 membered cycloalkyl ring may be N and / or O, and ring nitrogen may be Optionally substituted with C 1-3 alkyl or C 1-3 alkanoyl; one or two carbon atoms of the above-mentioned aliphatic chain may be replaced by 0, NH, NC 1-3 alkyl, NC 1-3 alkanoyl It can be and; alkyl or cycloalkyl group = O, OH, OC 1-3 alkyl, NH 2, NHC 1-3 alkyl, NHC 1-3 alkanoyl, N (C 1-3 alkyl) 2, N (C 1 -3 alkyl) (C < RTI ID = 0.0 > 1-3 < / RTI > alkanoyl) B is selected from the group consisting of COOH, COOR 5 , CONH 2 , CONHNH 2 , CONHR 5 , CONR 5 R 5 ' , CONHOH, CONHOR 5 , SO 3 H, SO 2 NH 2 , SO 2 NHR 5 , SO 2 NR 5 R 5' 3 H, PO (OH) ( OR 5), PO (OR 5) (OR 5 '), PO (OH) (NHR 5), PO (NHR 5) (NHR 5' means), tetrazolyl, and (each Lt; RTI ID = 0.0 > A < / RTI > Or the whole group YAB means a N (SO 2 R 4) ( SO 2 R 4 ') or NHSO 2 R 4, X is a bond, CH 2, (CH 2) 2, CH (CH 3), (CH 2) 3, CH (CH 2 CH 3), CH (CH 3) CH 2, CH 2 means CH (CH 3) and, Y represents O, NH, NR 4 , NCOR 4 , NSO 2 R 4 , With the proviso that when Y represents NH, NR 4 , NCOR 4 or NSO 2 R 4 , a) In addition, provided that the substituent R < 2 > comprises a saturated heterocyclic compound containing nitrogen, the heterocyclic compound is not substituted by hydrogen, methyl, ethyl, propyl or isopropyl in the imine nitrogen, b) a substituent "in R 4 and (or) R 4 'groups XNHR 4 or XNR 4 R 4, which optionally present in R 2 does not mean a C 1-4 alkyl, If the latter independently of one another, are unsubstituted or only C 1-6 alkyl, C 1-4 perfluoroalkyl, OC 1-6 alkyl, OC 1-4 alkyl perfluoroalkyl, COOH, COOC 1-6 alkyl, COC 1-6 alkyl, CONH 2, CONHR 4, N0 2, NH 2, NHCOR 4, NHS0 2 R 4, if optionally substituted by one or two halogen atoms from the group consisting of or a F, Cl, Br and I, however, B does not simultaneously mean COOH, SO 3 H, PO 3 H 2 or tetrazolyl, R 1 and R 2 independently of one another denote C 5-6 heteroaryl or phenyl, Here, the following compounds are excluded: [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] acetic acid methyl ester, 5 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] pentanoic acid methyl ester, 4 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] butanoic acid ethyl ester, 5 - [[1- (4-nitrophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] pentanoic acid methyl ester, 6 - [[1- (4-nitrophenyl) -2- phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 5 - [[1- (4-aminophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] pentanoic acid methyl ester, Amino] phenyl] -2-phenyl-1H-benzimidazol-6-yl] oxy] pentanoic acid methyl ester, Phenyl] -1H-benzimidazol-6-yl] oxy] pentanoic acid methyl ester, 5 - [[1- (3-nitrophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] pentanoic acid methyl ester, 6 - [[1- (3-nitrophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 5 - [[1- (3-aminophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] pentanoic acid methyl ester, Amino] phenyl] -2-phenyl-1H-benzimidazol-6-yl] oxy] pentanoic acid methyl ester, 5- [ Phenyl] -1H-benzimidazol-6-yl] oxy] pentanoic acid methyl ester) was added to a solution of 5 - [[1- [3- [2" claim-type="Currently amended] The method according to claim 1, R 1 is a monocyclic or bicyclic C 6-12 aryl group or a monocyclic or bicyclic 5- to 10-membered heteroaryl group having 1 to 2 heteroatoms selected from the group consisting of N, S or O (the above mentioned aryl or heteroaryl groups, independently of each other, may be substituted with substituent to three: F, Cl, Br, XOH, XOR 4, XOCOR 4, XOCONHR 4, XOCOOR 4, XCOR 4, XCN, XCOOH, XCOOR 4, XCONH 2, XCONR 4 R 4 ', XCONHR 4, XCONHOH, XCONHOR 4, XCOSR 4, XSR 4, NO 2, XNHR 4, XNR 4 R 4', R 4 ( wherein, in R 1 two If the substituents are in the ortho position to each other, they may be linked together in such a way that they form together methane diyl bisoxy, ethane-1,2-diyl bisoxy, propane-1,3-diyl or butane-1,4-diyl Benzimidazole < / RTI > [3" claim-type="Currently amended] 3. The compound according to claim 1 or 2, wherein R < 2 > is a monocyclic or bicyclic C6-10 aryl group or a monocyclic or heterocyclic group having 1 to 2 heteroatoms selected from the group consisting of N, A bicyclic 5- to 10-membered heteroaryl group (the above-mentioned aryl or heteroaryl groups may be substituted independently of each other by up to 3 substituents: F, Cl, Br, XOH, XOR 4 , XOCOR 4 , XOCONHR 4, XOCOOR 4, XCOR 4, XC (NOH) R 4, XC (NOR 4) R 4 ', XC (NO (COR 4)) R 4', XCOOH, XCOOR 4, XCONH 2, XCONHR 4, XCONR 4 R 4 ', XCONHOH, XCONHOR 4, XCOSR 4, XSR 4, XSOR 4, XSO 2 R 4, SO 2 NH 2, S0 2 NHR 4, SO 2 NR 4 R 4', N0 2, XNHR 4, XNR 4 R 4 ' , XNHSO 2 R 4 , XN (SO 2 R 4 ) SO 2 R 4' , XNR 4 SO 2 R 4 ' , R 4 wherein the two substituents of R 2 , if they are in ortho position to each other, Di-bishoxy, ethane-1,2-diyl bisoxy, propane-1,3-diyl, butane-1,4-diyl Which may be connected to each other in the form of a benzimidazole. [4" claim-type="Currently amended] The method according to any of items 1 to 3, wherein hanhang, R 3 are, independently of each other, hydrogen, F, Cl, Br, XOH, XOR 4, XOCOR 4, XOCONHR 4, XOCOOR 4, XCOR 4, XC (NOH) R 4, XC (NOR 4) R 4 ', XC (NO (COR 4)) R 4', XCN, XSR 4, XSOR 4, XSO 2 R 4, SO 2 NH 2, S0 2 NHR 4, S0 2 NR 4 R 4 ', N0 2, XNH 2, XNHR 4, XNR 4 R 4', XNHSO 2 R 4, XNR 4 SO 2 R 4 ', XN (SO 2 R 4) SO 2 R 4', XNHCOR 4, XNHCOOR 4 , XNHCONHR 4, or R 4 , wherein two substituents R 3 , if they are in the ortho position with respect to one another, together form a group selected from the group consisting of methanediylbisoxy, ethane-1,2-diylbisoxy, , 3-diyl, butane-1,4-diyl). [5" claim-type="Currently amended] 5. A compound according to any one of claims 1 to 4, wherein R 4 and R 4 ' independently of one another are CF 3 , C 2 F 5 , C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl , C 3-6 cycloalkyl, (C 1-3 alkyl-C 3-6 cycloalkyl), phenyl or 5- to 6-membered heteroaryl containing 1-2 N, S or O atoms, wherein phenyl and heteroaryl groups F, Cl, Br, CH 3, C 2 H 5, OCH 3, OC 2 H 5, CF 3 and C 2 F 5 can be optionally substituted with one or two substituents from the group consisting of and; in addition, 5 One of the ring atoms in the first cycloalkyl ring may be N or 0, and one or two ring atoms in the six-membered cycloalkyl ring may be N and / or O, and the ring nitrogen may optionally be substituted with C 1-3 alkyl Or C 1-3 alkanoyl). [6" claim-type="Currently amended] 6. The method according to any one of claims 1 to 5, And R 5 (which may be replaced by a, where one carbon atom 0, NH, NC 1-3 alkyl, NC 1-3 alkanoyl) R 5 'are independently from each other C 1-6 alkyl or C 3-7 cycloalkyl O-alkyl, -C 3 alkyl (where 1 ring atoms of 5-membered cycloalkyl ring, or N may be 0, 6, or 7-membered cycloalkyl ring in one or two ring atoms are N, and (or) 0 days And the ring nitrogen may be optionally substituted with C 1-3 alkyl or C 1-3 alkanoyl, and the above-mentioned C 1-6 alkyl moiety may be substituted with one of the above-mentioned cycloalkyls or N, S or O can be optionally substituted by from 5 to 6 membered heterocyclic aromatic compound having one to two heteroatoms selected from the group consisting of any two of the aforementioned alkyl and cycloalkyl portions are as CF 3, OH, OC 1-3 alkyl dog can be optionally substituted with a substituent of the following, the above-mentioned heteroaryl groups F, Cl, CF 3, CH 3, C 2 H 5, OCH 3, OC 2 H 5 , or R 5 and R 5 ' together with the nitrogen atom may contain another oxygen, nitrogen or sulfur atom and may be substituted by C 1-4 alkyl , C 1-4 alkoxy - C 0-2 alkyl, C 1-4 alkoxy-carbonyl, aminocarbonyl or phenyl. [7" claim-type="Currently amended] 7. A compound according to any one of claims 1 to 6, wherein A is C 1-10 alkanediyl, C 2-10 alkenyl, C 2-10 alkynediyl, or (C 5 -5 alkanediyl - C 3 -7cycloalkanediyl -C 0-5alkanediyl ), wherein one ring atom of the 5-membered cycloalkyl ring may be N or 0, and 1 or 2 ring atoms in the 6- or 7-membered cycloalkyl ring May be N and / or O, and the ring nitrogen may be optionally substituted with C 1-3 alkyl or C 1-3 alkanoyl, wherein one or two carbon atoms of the above-mentioned aliphatic chain may be replaced by O, NH, ≪ / RTI > NC 1-3 alkyl, NC 1-3 alkanoyl). [8" claim-type="Currently amended] The method according to any hanhang of items 1 to 7, B is a carbon atom of the group COOH, COOR 5, CONH 2, CONHR 5, CONR 5 R 5 ', CONHOH, CONHOR 5, or tetrazolyl (in each case, A Benzimidazole < / RTI > [9" claim-type="Currently amended] 9. Benzimidazole according to any one of claims 1 to 8, wherein X denotes a bond or methylene. [10" claim-type="Currently amended] 10. A benzimidazole according to any one of claims 1 to 9, wherein Y represents O. [11" claim-type="Currently amended] [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] acetic acid isopropyl ester, 3 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] propanoic acid methyl ester, 2 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] propanoic acid methyl ester, 4 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] butanoic acid isopropyl ester, 5 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] pentanoic acid isopropyl ester, 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid methyl ester, 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanoic acid isopropyl ester, 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide, Methoxy-6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide, N- (phenylmethoxy) -6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide, N-hydroxy-6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide, 7 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] heptanoic acid methyl ester, 6 - [[1- (3-nitrophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, 6 - [[2-phenyl-1- [3- (trifluoromethyl) phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[2-phenyl-1- [3- (trifluoromethyl) phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, 6 - [[1- (3-cyanophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[1- (3-cyanophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, 6 - [[1- (3-cyanophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid, 6 - [[1- (4-cyanophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[1- (4-cyanophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, 6 - [[1- (3-chlorophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[1- (3-chlorophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, 6 - [[1- (4-chlorophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[1- (4-chlorophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, 6 - [[1- (3-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[1- (3-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, 6 - [[1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, 6 - [[1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[1- (3,5-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[1- (3,5-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, 6 - [[1- (3-methoxyphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[1- (4-methoxyphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[1- (3,4-dimethoxyphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[1- [3,4- (methylenedioxy) phenyl] -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[1- [3,4- (methylenedioxy) phenyl] -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid, 6 - [[2-phenyl-1- (3,4,5-trimethoxyphenyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[2-phenyl-1- (3,4,5-trimethoxyphenyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid, 6 - [[2-phenyl-1- (3,4,5-trimethoxyphenyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, Phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, Phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid, < 6 - [[1-phenyl-2- [3- (trifluoromethyl) phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, 6 - [[2- (3-chlorophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[2- (3-chlorophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, 6 - [[2- (4-chlorophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[2- (4-chlorophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, 6 - [[2- (4-methylphenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[2- (4-methylphenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, 6 - [[1-phenyl-2- (4-pyridinyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [(1,2-diphenyl-5-nitro-1H-benzimidazol-6-yl) oxy] hexanoic acid methyl ester, 6 - [(1,2-diphenyl-5-nitro-1H-benzimidazol-6-yl) oxy] hexanoic acid isopropyl ester, Amino] -1,2-diphenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, Amino] -1,2-diphenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, Amino] -1,2-diphenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, 6 - [[1,2-diphenyl-5 - [[(3-methylphenyl) sulfonyl] amino] -1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, 6 - [[1,2-diphenyl-5 - [[(4-methylphenyl) sulfonyl] amino] -1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, Amino] -1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, 6 - [[ Phenyl] sulfonyl] amino] -1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, Amino] -1,2-diphenyl-1H-benzimidazol-6-yl] oxy] -hexanoic acid isopropyl ester, Amino] -1,2-diphenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, 6 - [[1,2-diphenyl-5 - [(propylsulfonyl) amino] -1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, 6 - [[5 - [(benzylsulfonyl) amino] -1,2-diphenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, 2 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] ethoxy] acetic acid methyl ester, 3- [2 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] ethoxy] -propanoic acid methyl ester, 6 - [[1- (3-nitrophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid ethyl ester, 6 - [[4-acetyl-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-5-yl] oxy] hexanoic acid methyl ester, Phenyl] -1H-benzimidazol-5-yl] oxy] hexanoic acid methyl ester, 6 - [[2-phenyl-1 - [(4- (thiomethyl) phenyl] -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[2-phenyl-1- (3-thienyl) -1H-benzimidazol-5-yl] oxy] hexanoic acid methyl ester, 6 - [[2-phenyl-1- (3-thienyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 4 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] butanoic acid methyl ester, Phenyl] -1H-benzimidazol-6-yl] oxy] -hexanamide, N- (phenylmethoxy) -6- [ N, N-dimethyl-6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide, N-isopropyl-6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide, 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] -1- pyrrolidin- 1 -yl-hexan- Amino] -1,2-diphenyl-1H-benzimidazol-6-yl] oxy] pentanoic acid methyl ester, Methyl] -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, (4-methoxyphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester , 6 - [[4- (acetyloxy) -1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[4-hydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[4-hydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid, 6 - [[7-methyl-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester. [12" claim-type="Currently amended] 6 - [[2-phenyl-1- (3-pyridyl) -1H-benzimidazol-5-yl] oxy] hexanoic acid methyl ester, 6 - [[2-phenyl-1- (3-pyridyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[2-phenyl-1- (4-pyridyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[2- (4-fluoro-phenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[2- (4-methoxyphenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[2- (4-bromophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[2- [4- (trifluoromethyl) phenyl] -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[1-phenyl-2- (benzothiene-2-yl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[1-phenyl-2- (benzothiene-2-yl) -1H-benzimidazol-6-yl] oxy] hexanoic acid, 6 - [[5-hydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, 6 - [[5-hydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid, 6 - [[5-methoxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid isopropyl ester, 6 - [[5-hydroxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[5-methoxy-1- (4-methylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, Amino] -1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoate Ester benzimidazol-6-yl] oxy] hexanoic acid methyl ester, (4-methoxy-phenyl) -lH-benzimidazol-6-yl < / RTI > ] Oxy] hexanoic acid methyl ester, (4-methoxyphenyl) -1H-benzimidazol-6-yl] -6- [ Oxy] hexanoic acid methyl ester, (4-methoxyphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] butanoic acid methyl ester , 2-phenyl-1H-benzimidazol-6-yl] oxy] pentanoic acid methyl ester , Amino] -1,2-diphenyl-1H-benzimidazol-6-yl] oxy] pentanoic acid methyl ester, (4-methoxyphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy ] Hexanoic acid methyl ester, Methyl] amino] -1- (4-methoxyphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoate ester, 6 - [[1- (indan-5-yl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[1- (indan-5-yl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid, 6 - [[1- (3-fluorophenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[2- (4-nitrophenyl) -1-phenyl-1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[1-phenyl-2- (3-pyridinyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, N- (cyclopropylmethoxy) -6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide, N-isobutoxy-6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide, Phenyl] -1- (3,4,5-trimethoxy-phenyl) -1H-benzimidazol-6-yl) oxy] hexanamide, N- (cyclopropylmethoxy) N-isobutoxy-6- [2-phenyl-1- (3,4,5-trimethoxyphenyl) -1H-benzimidazol-6-yl) oxy] hexanamide, N- (2-methoxyethyl) -6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide, N- (3-methoxy-propyl) -6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide, N-isobutyl-6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide, 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] -1- N, N-di (2-methoxyethyl) -6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide, N-isopentyl-6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide, 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide, N- 6 - [(1,2-diphenyl-1H-benzimidazol-6-yl) oxy] hexanamide, N- N-isopropyl-6- [[1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanamide, N, N-dimethyl-6- [[1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanamide, N, N-diethyl-6- [[1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanamide, N-isobutyl-6 - [[1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanamide, N-cyclopropyl-6 - [[1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanamide, N-cyclobutyl-6 - [[1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanamide, N-tert-butyl-6- [[1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanamide, 6-yl] oxy] l- (2-methoxymethyl) -pyrrolidin-l- -Hexan-1-one, (3-imidazol-1-yl-propyl) -6 - [[l- (3,4-dimethylphenyl) -2-phenyl-lH-benzimidazol-6-yl] oxy] hexanamide, 2-ylethyl) -6 - [[1- (3,4-dimethylphenyl) -2-phenyl-1H-benzimidazol-6-yl] oxy] hexanamide, 6-yl] oxy] heptane amide, N- (3-methoxy-propyl) -6 - [[1- (indan- (3-pyridyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[1- (4-methylphenyl) -2- (4-pyridyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[1- (4-methylphenyl) -2- (2-thienyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[1- (4-methylphenyl) -2- (3-thienyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[2- (3-indolyl) -1- (4-methylphenyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[1- (4-methylphenyl) -2- (2-furyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6 - [[1- (4-methylphenyl) -2- (3-furyl) -1H-benzimidazol-6-yl] oxy] hexanoic acid methyl ester, 6-yl] oxy] hexanoic acid methyl ester, 6 - [[1- (4-methylphenyl) -2- 6 - [[1- (4-methylphenyl) -2- (3-methyl-2-thienyl) -1H-benzimidazol- 6-yl] oxy] hexanoic acid methyl ester. [13" claim-type="Currently amended] 13. A method for the manufacture of a pharmaceutical formulation for the treatment or prevention of diseases associated with microglial activation of a compound of any one of claims 1 to 12. [14" claim-type="Currently amended] 13. A pharmaceutical formulation comprising at least one compound of any one of claims 1 to 12 and at least one excipient. [15" claim-type="Currently amended] Use of a benzimidazole of formula (II) in the manufacture of a pharmaceutical formulation for the treatment or prevention of diseases associated with the activation of microglial cells. ≪ (here, R 1 is a monocyclic or bicyclic C 6-12 aryl group or a monocyclic or bicyclic 5- to 10-membered heteroaryl group having 1 to 4 heteroatoms selected from the group consisting of N, S, or O (the above mentioned aryl or heteroaryl groups, independently of each other, may be substituted with substituent to three: F, Cl, Br, I, C (NH) NH 2, C (NH) NHR 4, C (NH ) NR 4 R 4 ', C (NR 4) NH 2, C (NR 4) NHR 4', C (NR 4) NR 4 R 4 ', XOH, XOR 4, XOCOR 4, XOCONHR 4, XOCOOR 4, XOCR 4, XC (NOH) R 4 , XC (NOR 4) R 4 ', XC (NO (COR 4)) R 4', XCN, XCOOH, XCOOR 4, XCONH 2, XCONR 4 R 4 ', XCONHR 4, XCONHOH , XCONHOR 4, XCOSR 4, XSR 4, XSOR 4, XSO 2 R 4, S0 2 NH 2, S0 2 NHR 4, SO 2 NR 4 R 4 ', N0 2, XNH 2, XNHR 4, XNR 4 R 4' , XNHS0 2 R 4, XN ( SO 2 R 4) (SO 2 R 4 '), XNR 4 SO 2 R 4', XNHCOR 4, XNHCOOR 4, XNHCONHR 4, tetrahydro-2,5-dioxide Sophie roll -1 Yl, 2,5-dihydro-2,5-dioxopyrrol-1-yl, 2,7-dihydro-2,7-dioxane Isoindol-1-yl, R 4 (where the two substituents of R 1 each other if there at the ortho position, they together methane diyl bis oxy, ethane-1,2-diyl-bis-oxy, propane-1,3-diyl , Butane-1,4-diyl)), R 2 is a monocyclic or bicyclic C 6-10 aryl group or a monocyclic or bicyclic 5- to 10-membered heteroaryl having 1 to 4 heteroatoms selected from the group consisting of N, S or O (Wherein the aryl or heteroaryl groups mentioned above may be substituted independently of each other by up to three substituents: F, Cl, Br, I, C (NH) NH 2 , C (NH) NHR 4 , C NH) NR 4 R 4 ', C (NR 4) NH 2, C (NR 4) NHR 4', C (NR 4) NR 4 R 4 ', XOH, XOR 4, XOCOR 4, XOCONHR 4, XOCOOR 4, XCOR 4, XC (NOH) R 4, XC (NOR 4) R 4 ', XC (NO (COR 4)) R 4', XCN, XCOOH, XCOOR 4, XCONH 2, XCONR 4 R 4 ', XCONHR 4, XCONHOH, XCONHOR 4, XCOSR 4, XSR 4, XSOR 4, XSO 2 R 4, SO 2 NH 2, S0 2 NHR 4, SO 2 NR 4 R 4 ', N0 2, XNH 2, XNHR 4, XNR 4 R 4 ', XNHSO 2 R 4, XN (SO 2 R 4) (SO 2 R 4'), XNR 4 SO 2 R 4 ', XNHCOR 4, XNHCOOR 4, XNHCONHR 4, tetrahydro-2,5-dioxide Sophie roll- Yl, 2,5-dihydro-2,5-dioxopyrrol-1-yl, 2,7-dihydro-2,7-di Soy stamp stone-1-yl, R 4 (wherein the two substituents on R 2, if one another, if in the ortho position, they methane diyl bis oxy, ethane-1,2-diyl-bis oxy together, propane-1,3- Diyl, butane-1,4-diyl)), R 3 are each independently hydrogen, F, Cl, Br, I , XOH, XOR 4, XOCOR 4, XOCONHR 4, XOCOOR 4, XCOR 4, XC (NOH) R 4, XC (NOR 4) R 4 ', XC (NO (COR 4 )) R 4 ' , XCN, XCOOH, XCOOR 4 , XCONH 2 , XCONHR 4 , XCONR 4 R 4' , XCONHOH, XCONHOR 4 , XCOSR 4 , XSR 4 , XSOR 4 , XSO 2 R 4 , SO 2 NH 2, S0 2 NHR 4 , S0 2 NR 4 R 4 ', N0 2, XNH 2, XNHR 4, XNR 4 R 4', XNHSO 2 R 4, XNR 4 SO 2 R 4 ', XN (SO 2 R 4) (SO 2 R 4 ' ), XNHCOR 4, XNHCOOR 4, XNHCONHR 4, tetrahydro-2,5-dioxide Sophie roll-yl, 2,5-dihydro-2,5-dioxide Sophie roll -1 -, 2,7-dihydro-2,7-dioxoisoindol-1-yl or one or two substituents which form R 4 , wherein two substituents R 3 , if they are in an ortho position to each other , Which together may be linked together in such a way as to form methane di bisoxy, ethane-1,2-diybisoxy, propane-1,3-diyl, butane-1,4-diyl) R 4 and R 4 'are independently C 1-4 perfluoroalkyl, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, (C 1- each other 3 alkyl-C 3-7 cycloalkyl), C 1-3 alkyl-C 6-10 aryl, C 1-3 alkyl- (5-10 membered heteroaryl containing 1-4 N, S or O atoms), C 6-10 aryl or 5 to 10 membered heteroaryl containing 1 to 4 N, S or O atoms, wherein the C 6-10 aryl and heteroaryl groups are optionally substituted with F, Cl, Br, CH 3 , C 2 H 5 , . N0 2, OCH 3, OC 2 H 5, CF 3 C 2 F 5 , or may be substituted by one or two substituents from the group consisting of, or ahnel rate (annelate) methane diyl bis oxy group or ethane- And one ring atom in the 5-membered cycloalkyl ring may be N or O, and one or two ring atoms in the 6- or 7-membered cycloalkyl ring may be substituted by N and / ) ≪ / RTI > 0, and the ring nitrogen may optionally be substituted with < Alkyl or Ci- 3 alkanoyl, R 5 and R 5 ' independently of one another are selected from the group consisting of C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl wherein one carbon atom is O, S, SO, SO 2 , NH, NC 1- 3 alkyl or NC 1-3 alkanoyl), C 3-7 cycloalkyl - C 0-3 alkyl wherein one ring atom of the 5 membered cycloalkyl ring may be N or 0, and 6 Or one or two ring atoms in the 7-membered cycloalkyl ring may be N and / or O, and the ring nitrogen may be optionally substituted with C 1-3 alkyl or C 1-3 alkanoyl), C 6- 10 aryl, or 5 to 10 membered heteroaryl containing 1 to 4 N, S, or 0 heteroatoms wherein all of the above alkyl, alkenyl and alkynyl chains are optionally substituted with one or more of the above-mentioned cycloalkyl, aryl, or heteroaryl And all the above-mentioned alkyl and cycloalkyl radicals may be substituted by one of CF 3 , C 2 F 5 , OH, OC 1-3 alkyl, NH 2 , NHC 1-3 alkyl, NHC 1-3 alkanoyl, N (C 3 alkyl) 2 , N (C 1-3 alkyl) (C 1-3 alkanoyl), COOH, CONH 2 , COOC 1-3 alkyl, aryl, and heteroaryl groups with one or two substituents from F, Cl, Br, CH 3 , C 2 H 5, N0 2, OCH 3, OC 2 H 5, CF 3, and the group consisting of C 2 F 5 Which may be substituted or may be accompanied by an annelated methanediylbisoxy or ethane-1,2-diylbisoxy group, Or R 5 and R 5 'can contain, one more oxygen, nitrogen or sulfur atom together with the N atom and C 1-4 alkyl, C 1-4 alkoxy -C 2 O-alkyl, C 1-4 alkoxy- Form a 5- to 7-membered heterocyclic compound which may be substituted with carbonyl, aminocarbonyl or phenyl, A is C 1-10 alkanediyl, C 2-10 Al canned yl, C 2-10 alkyne diyl, (C O-5 alkanediyl -C 3-7 cycloalkyl alkanediyl -C 0-5 alkanediyl ), (C 0-5 alkanediyl arylene -C 0-5 alkanediyl), (C 0-5 alkanediyl-heteroarylene -C 0-5 alkanediyl), (wherein aryl and heteroaryl groups F, Cl, Br, CH 3 , C 2 H 5, NO 2, OCH 3, OC 2 H 5, CF 3, optionally substituted with one or two substituents of the group from consisting of C 2 F 5, and; 5 One ring atom in the first cycloalkyl ring may be N or O, one or two ring atoms in the 6- or 7-membered cycloalkyl ring may be N and / or O, and the ring nitrogen may optionally be substituted with C 1-3 Alkyl or C 1-3 alkanoyl; one or two carbon atoms of the above-mentioned aliphatic chain may be replaced by O, NH, NR 4 , NCOR 4 , NSO 2 R 4 ; alkyl or cycloalkyl Is selected from the group consisting of F, OH, OR 4 , OCOR 4 , ═O, NH 2 , NR 4 R 4 ' , NHCOR 4 , NHCOOR 4 , NHCONHR 4 , NHSO 2 R Means 4 SH, it may be substituted) by two substituents or fewer from the group consisting of SR 4, and B is hydrogen, OH, OCOR 5, OCONHR 5 , OCOOR 5 ', COR 5, C (NOH) R 5, C (NOR 5) R 5', C (NO (COR 5)) R 5 ', COOH, COOR 5, CONH 2, CONHNH 2, CONHR 5, CONR 5 R 5 ', CONHOH, CONHOR 5, SO 3 H, S0 2 NH 2, S0 2 NHR 5, SO 2 NR 5 R 5', P0 3 H, PO ( OH) (OR 5), PO (OR 5) (OR 5 '), PO (OH) (NHR 5), PO (NHR 5) (NHR 5' means), tetrazolyl, and (in each case, the a group Or the whole YAB group means N (SO 2 R 4 ) (SO 2 R 4 ' ) or NHSO 2 R 4 , X represents a bond, CH 2, (CH 2) 2, CH (CH 3), (CH 2) 3, CH (CHCH 3), CH (CH 3) CH 2, CH 2 CH (CH 3) , and Y represents a bond, O, S, SO, SO 2 , NH, NR 4 , NCOR 4 , NSO 2 R 4 ) [16" claim-type="Currently amended] 16. The method of claim 15, R 1 of formula (II) is a monocyclic or bicyclic aryl group or a monocyclic or bicyclic 5- to 10-membered heteroaryl group having 1 to 2 heteroatoms selected from the group consisting of N, S or 0 the above-mentioned aryl or heteroaryl groups, independently of each other, may be substituted with substituent to three: F, Cl, Br, XOH, XOR 4, XOCOR 4, XOCONHR 4, XOCOOR 4, XCOR 4, XCN, XCOOH , XCOOR 4, XCONH 2, XCONR 4 R 4 ', XCONHR 4, XCONHOH, XCONHOR 4, XCOSR 4, XSR 4, NO 2, XNHR 4, XNR 4 R 4', R 4 ( wherein two substituents of R 1 If they are in ortho position to each other, they may be linked together in such a way as to form methane di bisoxy, ethane-1,2-diyl bisoxy, propane-1,3-diyl, butane-1,4-diyl) ). [17" claim-type="Currently amended] 17. The method according to claim 15 or 16, R 2 of formula (II) is a monocyclic or bicyclic aryl group or a monocyclic or bicyclic 5- to 10-membered heteroaryl group having 1 to 2 heteroatoms selected from the group consisting of N, S or O (the above mentioned aryl or heteroaryl groups, independently of each other, may be substituted with substituent to three: F, Cl, Br, XOH, XOR 4, XOCOR 4, XOCONHR 4, XOCOOR 4, XCOR 4, XC ( NOH) R 4 , XC (NOR 4 ) R 4 ' , XC (NO (COR 4 )) R 4' , XCN, XCOOH, XCOOR 4 , XCONH 2 , XCONR 4 R 4 , XCONHR 4 , XCONHOH, XCONHOR 4 , XCOSR 4, XSR 4, XSOR 4 , XSO 2 R 4, SO 2 NH 2, S0 2 NHR 4, SO 2 NR 4 R 4 ', N0 2, XNH 2, XNHR 4, XNR 4 R 4', XNHSO 2 R 4, XN (SO 2 R 4 ) (SO 2 R 4 '), XNR 4 SO 2 R 4', XNHCOR 4, XNHCOOR 4, XNHCONHR 4, R 4 ( wherein the two substituents on R 2, if each other ortho position , They may be taken together to form methane diyl bisoxy, ethane-1,2-diylbisoxy, propane-1,3-diyl, butane- Use, which means that can be connected to each other)) in such a manner as to form a. [18" claim-type="Currently amended] 18. The method according to any one of claims 15 to 17, Formula R 3 are each independently hydrogen of II, F, Cl, Br, XOH, XOR 4, XOCOR 4, XOCONHR 4, XOCOOR 4, XCOR 4, XC (NOH) R 4, XC (NOR 4) R 4 ', XC (NO (COR 4)) R 4 ', XCN, XSR 4, XSOR 4, XSO 2 R 4, SO 2 NH 2, S0 2 NHR 4, S0 2 NR 4 R 4', N0 2, XNH 2, XNHR 4 , XNR 4 R 4 ' , XNHSO 2 R 4 , XNR 4 SO 2 R 4' , XN (SO 2 R 4 ) (SO 2 R 4 ' ), XNHCOR 4 , XNHCOOR 4 , XNHCONHR 4 or R 4 One or two substituents wherein two substituents R < 3 > are taken together if they are in ortho position to each other, they together form a saturated or unsaturated, 4-diyl. ≪ / RTI > [19" claim-type="Currently amended] 19. The method according to any one of claims 15 to 18, With the general formula II of R 4 and R 4 'independently of each other CF 3, C 2 F 5, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 3-6 cycloalkyl, (C 1-3 alkyl-C 3-6 cycloalkyl), C 1-3 alkylaryl, C 1-3 alkylheteroaryl, monocyclic aryl, or a 5-6 membered ring containing 1-2 N, S or O atoms heteroaryl (wherein aryl and heteroaryl groups F, Cl, Br, CH 3, C 2 H 5, NO 2, OCH 3, OC 2 H 5, CF 3, and 1 or 2 of the group from consisting of C 2 F 5 Or one of the ring atoms in the 5-membered cycloalkyl ring may be substituted by an N, N, or N-disubstituted amino group, or may be an annelated methanediylbisoxy or ethane-1,2-diylbisoxy group; Or 0, and one or two ring atoms of the six-membered cycloalkyl ring may be N and / or O, and the ring nitrogen may be optionally substituted with C 1-3 alkyl or C 1-3 alkanoyl Meaning that Applications. [20" claim-type="Currently amended] 20. The method according to any one of claims 15 to 19, R 5 and R 5 ' of formula II are each independently of the other C 1-6 alkyl, wherein one carbon atom may be replaced by 0, NH, NC 1-3 alkyl, NC 1-3 alkanoyl, or C 3-7 cycloalkyl, -C 3 O-alkyl (wherein one of the ring atoms of 5-membered cycloalkyl ring, or N may be 0, 6, or 7-membered cycloalkyl ring in one or two ring atoms are N and ( Or 0), and the ring nitrogen may be optionally substituted with C 1-3 alkyl or C 1-3 alkanoyl; the above-mentioned C 1-6 alkyl moiety may be substituted with one of the above cycloalkyls, or N, S or O, and all of the above-mentioned alkyl and cycloalkyl moieties may be substituted with a group consisting of CF 3 , OH, OC 1-3 alkyl, and the like. may be substituted with two substituents or fewer from, the above-mentioned heteroaryl groups F, Cl, CF 3, CH 3, C 2 H 5, OCH 3, O C 2 H 5 ), or R 5 and R 5 ' together with the nitrogen atom may contain another oxygen, nitrogen or sulfur atom, and C 1 4- alkyl, C 1-4 alkoxy - C 0-2 alkyl, C 1-4 alkoxy-carbonyl, aminocarbonyl or phenyl. [21" claim-type="Currently amended] 21. The method according to any one of claims 15 to 20, A is of the formula II C 1-10 alkanediyl, C 2-10 Al canned yl, C 2-10 alkyne diyl, (C O-5 alkanediyl -C 3-7 cycloalkyl -C 0-5 alkanediyl Alkanoyl), or (C 0-5 alkanediyl-heteroarylene-C 0-5 alkanediyl), wherein the optionally present heteroaryl group is F, Cl, Br, CH 3 , C 2 H 5 , One of which may be substituted by one or two substituents selected from the group consisting of NO 2 , OCH 3 , OC 2 H 5 , CF 3 and C 2 F 5 ; furthermore, one ring atom of the five membered cycloalkyl ring may be substituted by N or 0, one or two ring atoms in the 6- or 7-membered cycloalkyl ring may be N and / or O, and the ring nitrogen may be optionally substituted with C 1-3 alkyl or C 1-3 alkanoyl One or two carbon atoms in the aliphatic chain may be replaced by O, NH, NC 1-3 alkyl, NC 1-3 alkanoyl, NSO 2 C 1-3 alkyl; the alkyl or cycloalkyl moiety may be substituted with up to two F atom or OH, OC 1-3 alkyl, OC 1-3 alkanoyl, O, NH 2, NHC 1-3 alkyl, N (C 1-3 alkyl) 2, NHC 1-3 alkanoyl, N (C 1-3 alkyl) (C 1-3 alkanoyl), NHCOOC 1-3 alkyl , NHCONHC 1-3 alkyl, NHSO 2 C 1-3 alkyl, SH, SC 1-3 alkyl. [22" claim-type="Currently amended] 22. A compound according to any one of claims 15 to 21 wherein B of the formula II is selected from the group consisting of hydrogen, OH, OCOR 5 , OCONHR 5 , OCOOR 5 , COOH, COOR 5 , CONH 2 , CONHR 5 , CONR 5 R 5 ' , CONHOR 5 , or tetrazolyl (in each case bound to the carbon atom of the group A). [23" claim-type="Currently amended] Of claim 15 to A method according to any one of claim 22, wherein the purpose of the X of formula (II) means a bond or CH 2. [24" claim-type="Currently amended] 24. Use according to any one of claims 15 to 23, wherein Y in formula (II) represents a bond, O, S, NH, NR 4 , NCOR 4 or NSO 2 R 4 .
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同族专利:
公开号 | 公开日 NO20023362L|2002-09-13| TWI287005B|2007-09-21| CN1395568A|2003-02-05| MXPA02005742A|2002-09-18| BG106821A|2003-01-31| SI1246808T1|2011-12-30| CA2396227A1|2001-07-19| WO2001051473A8|2002-01-03| HU228366B1|2013-03-28| NO20023362D0|2002-07-12| HRP20020664B1|2012-03-31| AT520669T|2011-09-15| CN1301975C|2007-02-28| EA006302B1|2005-10-27| HU0204011A3|2003-07-28| CZ303726B6|2013-04-10| IL150150D0|2002-12-01| DK1246808T3|2011-12-05| MEP13308A|2010-10-10| JP2003523961A|2003-08-12| CA2396227C|2012-03-20| AU4233201A|2001-07-24| BG65858B1|2010-03-31| IL150150A|2014-03-31| EA200200742A1|2002-12-26| SK10002002A3|2003-02-04| UA75589C2|2002-10-15| CZ20022420A3|2002-10-16| RS51860B|2012-02-29| NZ519326A|2005-02-25| EP1246808B1|2011-08-17| EP1246808A1|2002-10-09| PL209573B1|2011-09-30| YU45702A|2005-03-15| EE200200390A|2003-10-15| WO2001051473A1|2001-07-19| ZA200206470B|2004-04-28| BR0107628A|2002-10-08| ES2372026T3|2012-01-13| PL356091A1|2004-06-14| SK287527B6|2011-01-04| HRP20020664A2|2005-04-30| PT1246808E|2011-11-30| NO326408B1|2008-12-01| KR100703908B1|2007-04-05| HU0204011A2|2003-05-28| CY1112962T1|2016-04-13| AU782993B2|2005-09-15| EE05515B1|2012-02-15|
引用文献:
公开号 | 申请日 | 公开日 | 申请人 | 专利标题
法律状态:
2000-01-14|Priority to DE10002898 2000-01-14|Priority to DE10002898.5 2001-01-12|Application filed by 쉐링 악티엔게젤샤프트 2002-08-03|Publication of KR20020063629A 2007-04-05|Application granted 2007-04-05|Publication of KR100703908B1
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