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    • 专利摘要:
    1. METHOD FOR OBTAINING DERIVATIVES OF BENZOYLFENSH shiperidine of the general formula where K, -H3 are the same or different and mean a hydrogen atom or halogen, oxy, trifluoromethyl, lower alkyl or lower alkoxy; R. a hydrogen, bromine or chlorine atom, a nitro or NRR group, (where R and R are the same or different and mean a hydrogen atom, lower alkyl or C02R, where R is lower alkyl or benzyl); R, -and R are the same or different and represent a hydrogen atom, a lower alkyl, hydroxy, phenyl or benzyl, characterized in that 2halogen-5-nitrobenzophenone of the general formula: (II) where R, -RJ have the indicated values; (O X is a halogen atom, reacting with a piperidine of the general formula tG (III) where RS and Rg have the indicated values, and the resulting nitro derivative of the general; formula R, III) (IV) where R and R have the indicated values, or are isolated, or in the case when R - NH ,, is reduced, then you
    公开号:SU1147251A3
    申请号:SU823456997
    申请日:1982-06-28
    公开日:1985-03-23
    发明作者:Мажуа Бернар；Беллами Франсуа；Додеи Пьер；Робэн Жак
    申请人:Сосьете Де Решерш Эндюстриэль (С.О.Р.И.) (Фирма)；
    IPC主号:
    专利说明:

    or, if necessary, the α-obtained amine is alkylated, or the amino group is deaminated or substituted for a bromine or chlorine atom by diazotizing the amine with sodium or potassium nitrite at 0 ° C, followed by replacing the resulting diazo group with a hydrogen atom, bromine or chlorine, and the target product are highlighted.
    2. The method of Claim 1, wherein the compound of the general formula (II) is reacted with the piperidine of the general formula (III) in an inert organic solvent, such as an aromatic carbon, hydrogen, ether or alcohol,
    7251
    the presence of a base, with a molar ratio of compounds of the general formulas (II) and (III) equal to at least 1: 1.1, at a temperature of from 15 ° C to the boiling point of the reaction mixture.
    3. The method according to claim 1, characterized in that the reduction reaction of the compound of the general formula (IV) is carried out in an inert organic solvent, for example, in an alcohol or in a mixture of alcohol and water, in the presence of iron and acid at a temperature from to the boiling point of the reaction mixture .
    in ethnyl acetate. The suspension obtained is treated with sodium bicarbonate and the organic phase is washed with water, then dried and evaporated. Obtain 3.9 g of solid product, which gives after recrystallization in hexane 2.9 g (yield 44%) of the target product so pl. 89 ° C. I The NMR spectrum of the product from example 2 (80 MN, CDClj), given per million: 0.70 (intensity 5); 1.37 (intensity 3); 2.50 and 2.80 (intensity 4); 3.58 (intensity 2); 6.80 (intensity 3); 7.35 and 7.70 (intensity 4). Similarly, when carrying out the process at 15 ° C for 5 h in ethanol, the desired product is obtained with a yield of 21%. Example 3. 2- (4-Methyl-1-piperidinyl) -5- (N-ethoxycarbonyl) phenyl- (4-chlorophenyl) -methanone (code 610). Under a nitrogen atmosphere, a mixture of 0.01 mol (3.3 g) of the product obtained in accordance with Example 1, 2.4 g of 0.1 mol (10.8 g) of ethyl chloroformate in toluene was stirred at ambient temperature for 15 h. The reaction mixture is then diluted with water. The aqueous phase is extracted in ethyl acetate, then the organic phases are collected and washed with water, dried over magnesium sulfate. After evaporation of the solvent, recrystallization in hexane, 2j9 g (yield 72%) of the desired product are obtained, m.p. 132 ° C. Example 4. 2- (4-Methyl-1piperidinyl) -phenyl-phenylmethanone (code 611). 0.01 mol (3 g of the product of example 23, code 592) of 2- (4-methy 1 1-piperidinyl) -5-aminophenyl-phenylmethanone is dissolved in ethanol. It is cooled to 0 ° C, then 10 ml of sulfuric acid and 0.02 mol (1.4 g) of sodium nitrite are added successively. I stirred for 1 hour at 0 s, the reaction mixture was allowed to warm to room temperature (15-20 ° C). Then 0.65 g of activated copper was added and the reaction mixture was heated at another 30 ° C temperature, which was maintained for 1 hour. After hydrolysis and neutralization extract the mixture into methylene chloride, then wash with water and dry by evaporation of the solvent. They recrystallize in ethanol. and get 1 g (yield 37%) of the desired product, so pl. . Example 5. 2- (4-Methyl-1-. Piperidinyl) -5- (dimethylaminophenyl) (4-chlorofenyl) -methanone (code 612). 0.02 mol (6.6 g) of the product of Example 2 (code 442) is dissolved in 80 ml of dimethylformamide, the mixture is heated to 70 ° C. Then a mixture of formic acid and formalin is added dropwise, with each ingredient of the mixture in a 30% aqueous solution, 0.2 mol of each of these two ingredients is used and the mixture is shaken for 2.5 hours at 70 C. Then the reactive mixture Pour into sodium bicarbonate solution and isolate with ethyl acetate. The organic phase is then washed with water until the pH is neutral, then dried over magnesium sulphate, decolorized and evaporated. The oily product obtained is purified on a silica column (eluant hexane-acetone in a volume ratio of 10: 1 and recrystallized in hexane. 2.2 g are obtained (yield 29.5% of the desired product, mp 99.5 ° C. Example 6. 2- (4-Metsh1-1piperidinyl) -5-methylamino-phenyl - (4 chlorophenyl) -methanone i (code 613). A mixture of 0.01 mol (4.8 g) of the product obtained is boiled for 5 h. in accordance with Example 2 (compound 22), in hydrochloric acid ethanol (5 NHC1). Ethanol is evaporated, the resulting product is rinsed with ethyl acetate, and then hydrolyzed. extract with ethyl acetate. Dry by evaporation of the solvent. The resulting product is purified on a silica gel column, Seluant: hexane-acetone.) 2.5 g (yield 70%) of the desired product are obtained, mp. Example 7. 2- (4-Methyl -1 piperidinyl) -5-aminophenyl - (3-chlorophenyl) -methanone is obtained according to examples 1 and 2 (recrystallization in a mixture of hexane - diisopropylether 12: 1; 13 by volume), yield 35.7%. Example p 8. 2- ( 4-; 1-methyl-1-piperid in yl) -5-aminophenyl - (2-chlorophenyl) -methanone (code 747) is obtained according to Example 1 (recrystallization in ethanol-hexane 1: 1 by volume) and p Example 2 (recrystallization in hexane-diisopropylether 1: 1 by volume, yield 54%. Example 9. 2- {4-Methyl-1piperidinyl) -5-aminophenyl - (3.4ioxomethylphenyl) -methanone (code 69-7) was prepared according to examples 1 and 2 (recrystallization from hexane), 55% yield. Example 10. 2- (1-Piperidine yl) -5-aminophenyl - (4-chlorophenyl) -methanone (code 635) was prepared according to example 1 (recrystallization in ethanol) and example 2 (recrystallization in hexane), yield 68%. Example 11. C2- (3-M & thyl-1piperidinyl) -5-aminophenyl - (4-chlorophenyl) -methanone (code 695) is prepared according to example 1 (recrystallization of toluene-diisopropylether 3: 7 by volume) and example 2 (recrystallization in hexane-diisopropylether 1: 1 by volume), yield 63%, Example 12. C2- (4-Methyl-1piperidinyl) -5-aminophenyl - (4-methylphenyl) -methanone (code 655) is obtained I according to examples 1 and 2 (ne tion of ekrista in hexane), yield 88%. Example 13. 2- (4-Melyl-1piperidinyl) -5-aminophenyl -2,4-dimethyl (fensh1) -methanone (code 659) was prepared according to examples 1 and 2 (purification on a silica column elution with a mixture of hexane - acetone 7: 3 by volume - followed by crystallization in hexane), yield 63%. Example 14. (4-Methyl-1-p-peridinyl) -5-aminophenyl - (4-fluorophenyl) -methanone (code 660) was prepared according to example 2: cleaning on silica gel (eluting with luol), and example 2 : (recrystallization in hexane), yield 44%. Example 15. 2- (3,5-Dimethyl 1-piperidinyl) -5-aminophenyl1- (4-chloro-phenyl) -methanone (code 637) was prepared according to examples 1 and 2 (recrystallization in hexane), yield 56%,. Example 16, f2- (2-Methyl-1-piperidinyl) -5-aminophenyl 7- (4-chlorophenyl) -methanone (code 647) was prepared according to example 1 (recrystallization in ethanol) and example 2 (recrystallization in hexane), yield 50 Example 17. 2- (4-Methyl-1piperidinyl) -phenyl - (4-chlorophenyl) methanone (code 634) was prepared according to Example 4: purification on a silica column (elution in benzene), 38% yield. Example 18. 2- (4-Methyl-1piperidinyl) -5-chlorophenyl-4-chlorophenyl-methanone- (compound 18, code 633). The tetrafluoroborate of the diazo product from Example 2, obtained as a result of reaction with sodium nitrite in tetrafluoroboric acid, is obtained. Then 0.02 mol (8.6 g) of this diazon is added dropwise to a solution of 2.75 g of cupric chloride in DMSO. Stir for 30 minutes, filter, extract with ethyl acetate, dry and evaporate the solvent. Simultaneously with the desired product, the product from example 17 (code 634; t, mp. 69 ° C) is formed. After purification on a column of silica (eluant: benzene) and evaporation of the residue, 3 g (yield 40%) of the desired product is obtained, t, melt . 109 ° C. Example 19, 2 (4-Methyl-1piperidinyl) -5-aminophenyl - (4-oxomethylphensh1) -methanone (code 746) is obtained according to examples 1 and 2: purification on a column of silica (elution in toluene — CHjCOjCjHj 4: 1 by volume), yield 61.3%, Example 20, C2- (4-Methyl-1piperidinyl) -phenyl - (4-oxomethylphenyl) -methanone (code 704) was obtained according to example 4: purification on a column of silica (eJJ) in hexane - CHjCOjC H ,, - 1: 1. by volume). Example 21, 2- (4-Metsh1-1-piperidinyl) -5-, 5-H- (benzyloxycarbonylamino) -phenyl- (4-chlorophenyl) -methanone is obtained according to example 3 starting from 0.02 mol (6.6 g) of the compound 2 and 17 g of benzyl chloroformate, yield 71,% (6.6 g). Example 22, 2- (4-Methyl-1piperidinyl) -: 5- (S-benzyloxycarbonyl-S-methylamino.) - Phenyl-chlorophenylmethanone. In a nitrogen atmosphere is stirred for 30 minutes in THF 0.012 mol (0.3 g) sodium hydride and 0.012 mol (5.5 g) of the product from example 2. Then 0.18 mol (2.6 g) of methyl iodide dissolved in THF is added dropwise. The mixture is allowed to warm to ambient temperature (15-20 ° C ) and continue stirring for 15 hours. After hydrolysis of the reaction mixture, it is extracted with ethyl acetate, then the organic phases are washed with water. After drying and evaporation of the solvent, 5 g (yield 85%) of the desired product are obtained. Example 23 | 2- (4-Methyl-1piperidylNyl) -5-aminophenyl-phenylmethanone (code 592) was prepared according to examples 1 and 2 (recrystallization in hexane), yield 35%. Example 24. 2- (4-Methyl-1piperidinyl) -5-aminophene1 - (3-chloro4-chlorophenyl) -methane (code 698) was prepared according to examples 1 and 2 (recrystallization in hexane), yield 41% Example 25. 2 - (4-Methyl-1piperidinyl) -5-aminophenyl- (3,4,5-trimethylphenyl) -methanone (code 727) is obtained according to examples 1 and 2 (recrystallization in toluene), yield 65%. Example 26. 2- (4-Methyl-1piperidinyl) -5-aminophenyl - (4-bromophenyl) -methanone (code 736) is prepared according to examples 1 and 2 (recrystallization in hexane and diisopropylether), yield 48%. Example 27. 2- (4-Tpremethylpiperidinyl) -5-aminophenyl J- (4-5 {loprophenyl) -methanone (code 757) was prepared according to example 1 (recrystallization in toluene) and example 2 (recrystallized in hexane-diisopropylether 4 : 1 to), yield .67%. Example 28. 2- (4-Ethyl-1-pi peridinyl) -5-aminophenyl - (4-chlorophenyl) -methanone is obtained according to example 1 (recrystallization in SNdCOg N) and example 2 (recrystallization in hexane), yield 84% . Example 29. 2- (4N-butyl1-piperidinyl) -5-aminophene-- - (4-chloro-phenyl) -methanone is prepared according to Example 1 (recrystallization in Hj) and Example 2 (recrystallization in hexane). yield 88%. Example 30. 2- (4-Benzyl-1piperidinyl) -5-aminophenylJ- (4-chlorophenyl) methane is prepared according to Examples 1 and 2 (recrystallization in d isopropyl ether), yield 77%. Example 31 2- (4-Phenyl-1piperidinyl) -5-aminophenyl-3- (4-chlorophenyl) -methanone is obtained according to measures I and 2 (recrystallization in a toluene-diisopropylether 1: 1 by volume). PRI me R 32. I 2- (4 - Hydroxy1-piperidimi.G1) -5-amnofeni.ch | - (4-chlorophenyl) -methane is obtained honeycomb-a-case of example 1 (recrystallization in CHjCOjC H, -) II example 2: purification on a column of silica (elution in a mixture of toluene -., - 1: 1 by volume), yield 70%. Example 33. 2- (4-Methyl-1piperidine) -5-aminophenyl - (2,4-dichlorophenyl) -methanone is prepared according to example 1 (recrystallization in a toluene-diisopropylether 3: 7 by volume) and example 2 (recrystallization in a diisopropyl ether ), yield 60%. Melting points are given in table. one. . The products of formula (I) are used in therapy as immunostimulating and immunoprophylactic agents. They are prescribed for cancer immunotherapy, as a stimulator of antiviral and anti-infective resistance, and in the treatment of autoimmune diseases (in particular, rheumatic polyarthritis). As a result of tests conducted with products that are the subject of the invention, the effects of lymphocyte stimulation in mice and toxicity were studied. Stimulation of lymphocytes in mice. Lymphocytes (5x10 cells), which were isolated from spleen squabbles (DBA / 2), are incubated for 36 hours at 37 ° C in an oxygen atmosphere with 5% COj in a culture medium (PPM1 1640) containing 10 wt.% Of calf embryo serum. (100 / l); solution of lectins at the rate of 5 g / ml of phytohemaglutinin and Poukvid (MlB) and test material. Activity is determined by measuring the radioactivity obtained by irradiating for 24 hours 2yvli (i.e., 7, Dx10 becquerels) with thymidine treated with tritium relative to the control culture. The results are presented in Table. 2. Toxicity (1) L-50 and DL-0) is determined by the intraperitoneal method in mice according to C.T. Litchfeld. The results are shown in Table. 3. In addition, the product from Example 2 (cipher 442) was investigated in accordance with It114725112 with the test of residual hyperdiability before sensitization, the product
    sensitivity. At a dose of 5 Ig / kg, applied to myppie for three
    from example 2 leads to a decrease in half the residual hypersensitivity.
    7464-OCHj NN
    7044-OSS NN
    592ННН
    6983-C1
    7273-СНз 4-СНэ5-СНз
    7364-Br HN
    7574-C1 NN
    -4-C1 NN
    -4-C1 NN
    -4-C1 HH.
    -4-C1 NN
    -%
    -4-C1 NN
    2-C1 4-C1 N
    Note. Oil, p 1.5950.
    399 442 610 612 613 747 697 635
    64
    H
    H
    108
    H
    94
    H
    127
    H
    105
    H
    h)
    109
    H
    92
    H
    ,
    103
    H
    H
    109
    H
    144
    H
    71
    H
    117
    H
    table 2
    ++
    +++
    ++
    +
    +.
    15 Note. +++ +++ Tabli
    16 Continuation of table 2
    stimulation from 0 to .50%; stimulation from 50 to 100%; stimulation exceeding 100%, ca 3
    权利要求:
    Claims (3)
    [1]
    1. METHOD FOR PRODUCING BENZOYLPHENYLPIPERIDINE DERIVATIVES of the general formula alkyl or CO 2 R, where R is lower alkyl or benzyl);
    Rj-hR ^ are the same or different and mean a hydrogen atom, lower alkyl, hydroxy, phenyl or benzyl, characterized in that 2-halogen-5-nitrobenzophenone is of general form (II)
    X where R, have the indicated
    X is a halogen atom, interacting with nom of the general formula pO, the values of piperidium- (III) values ,!
    where Ry and R e have the indicated and obtained nitro derivative of the general formula
    GO SP where R, -R 3 are the same or different and mean a hydrogen or halogen atom, hydroxy, trifluoromethyl, lower alkyl or lower alkoxy;
    R ^ is an atom of hydrogen, bromine or chlorine, a nitro or NR'R group, (where R 'HR ff are the same or different and mean a hydrogen atom, the lowest
    R is where R and R * are indicated, or isolated, or when R "- NH ,, is reduced, then 1147251 is isolated or, if necessary, the obtained amine is alkylated, or the amino group is deaminated or substituted with a bromine atom or chlorine by diazotization of the amine with sodium or potassium nitrite at 0 ° C, followed by substitution of the obtained diazo group with a hydrogen, bromine or chlorine atom, and the target product is isolated.
    [2]
    2. The method of pop. 1, characterized in that the interaction of the compounds of General formula (II) with piperidine of General formula (III) is carried out in an inert organic solvent, such as an aromatic hydrocarbon, ether or alcohol, in the presence of a base, in a molar ratio of compounds general formulas (II) and (III), equal to at least 1: 1.1, at a temperature of from 15 ° C to the boiling point of the reaction mixture.
    [3]
    3. The method of pop. 1, characterized in that the reduction reaction of the compounds of General formula (IV) is carried out in an inert organic solvent, for example in alcohol or in a mixture of alcohol and water, in the presence of iron and acid at a temperature of from 15 ° C to the boiling point of the reaction mixtures.
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    同族专利:
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    ZA824536B|1983-04-27|
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    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US3202655A|1962-04-27|1965-08-24|Yvon G Perron|6-[alpha-substituted-alpha- acetamido] penicillanic acid and nontoxic salts thereof|
    NL298186A|1962-11-13|
    FR1375300A|1962-11-13|1964-10-16|Hoffmann La Roche|Benzophenone derivatives and their preparation|
    FR1403939A|1963-06-07|1965-06-25|Hoffmann La Roche|Process for the preparation of benzodiazepine derivatives|
    FR1526708A|1966-06-13|1968-05-24|Upjohn Co|1.3-amino alcohols, their intermediates and derivatives and process for their preparation|
    US3668199A|1966-06-13|1972-06-06|Upjohn Co|1,3-aminoalcohols|
    FR1530393A|1966-07-11|1968-06-21|Hoffmann La Roche|Process for the preparation of piperidine derivatives|
    IE34545B1|1969-10-01|1975-06-11|Continental Pharma|Amino-alcohols,their salts and process for preparing the same|
    HU167950B|1973-07-26|1976-01-28|
    US4064121A|1973-07-26|1977-12-20|Richter Gedeon Vegyeszeti Gyar Rt.|Substituted nitrobenzophenone derivatives and a process for the preparation thereof|
    HU167949B|1973-07-26|1976-01-28|
    US4021563A|1975-02-06|1977-05-03|Sven Eric Harry Hernestam|Method of treating cardiac arrhythmia with γ-piperidino-butyrophenones|
    IE49998B1|1979-08-06|1986-01-22|Merrell Dow Pharma|4-piperidine derivatives|IL82573D0|1986-05-30|1987-11-30|Sori Soc Rech Ind|Preparation of benzoylphenyl-piperidine derivatives|
    FR2620027A1|1987-09-09|1989-03-10|Fournier Innovation Synergie|NEW USE OFPHENYL) --METHANONE|
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    AU4011501A|2000-03-10|2001-09-24|Pharmacia Corp|Method for the preparation of tetrahydrobenzothiepines|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    FR8112745A|FR2508445B1|1981-06-29|1981-06-29|
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