• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    Die Erfindung betrifft neue 7-(Azabicycloalkyl)-chinolon- carbonsäure- und -naphthyridoncarbonsäure-Derivate der allgemeinen Formel (I) in der R1, R2, R3, X1 und A die in der Beschreibung angegebene Bedeutung haben, Verfahren zu ihrer Herstellung sowie diese enthaltende antibakterielle Mittel und Futterzusatzstoffe.
    公开号:SU1538897A3
    申请号:SU874028796
    申请日:1987-01-15
    公开日:1990-01-23
    发明作者:Петерсен Уве；Гроге Клаус；Шенке Томас；Гагеманн Германн；Цейлер Ганс-Йоахим；Георг Метцгер Карл
    申请人:Байер Аг (Фирма)；
    IPC主号:
    专利说明:

    (Gsn
    N
    it
    i6) (i-v)
    Y
    R
    R4-CH3, benzyl; X, - F or N02, A - nitrogen or CR5 with R5 H, F, C1, N02; or R, and A-0-CH2-CH- (CH) b, and if X F; and either N, or cyclopropyl, or R with R, -0-CHg-CH- (CH3) -, then Rrf radical if Xt F, A-CH -, - CCl-, -CF-, or A and R, H) -CH2-CH- (SNE), then R3 radical b or d with, or their acid additive salts or (hydrates with antibacterial action, which can be used)
    WITH
    It is called in medicine. Synthesis is carried out from the compound of the common f-ly, where instead of R3 there is halogen, which is treated with R3H or its hydro- or dihydrochloride, if necessary, in the presence of an acid binding agent, followed by isolation of the desired product in free form or in the form of the necessary salts or hydrates. The novel compounds have improved antibacterial activity. 1 tab.

    W
    This invention relates to a process for the preparation of novel compounds with an antibacterial effect, in particular to
    Method for producing quinoline or naphthyridinecarboxylic acid derivatives
    Cun
    3.3 g (9.2 mmol) 1-cyclopropyl-7 (1, -dia zabi cyclo 3, 2,1 -octane-.) 6-fluoro-1,4-dihydro-oxo-3-nolinecarboxylic acid (betaine from Example 1) and 1.8 g (A, 6 mmol) of embonic acid in 35 ml of tlycolonomethyl ether are heated under reflux for A h. The suspension is cooled, the crystals are sucked off, washed with ethanol and dried under vacuum at 120 ° C. A is obtained, 7 g of 1-cyclopropyl-7 hemiyembonate 7 (1, -Diazabicyclo 3,2,1 oct-4
    40
    Cun
    xHCl
    Example 1 is repeated, starting with 7-chloro-1-qi clopropyl-6-fluoro-1, k-di-hydro-oxo-1,8-naphthydrin-3-carboxylic acid. Get 1-cyclopropyl-7 (1,4-diazabicyclo-3,2,1-oct-4-yl) -6-fluoro-1, -dihydro-A-oxo-1,8-naphthydrin 3-carboxylic acid hydrochloride from m.p. 303-307 ° C (decomposition).
    Example 6 „
     YCOOH 1 xHCl
    N) N N
    515388
    Example 1 is repeated, based on
    -ChLOr-1 -CYCLOGFOPIL-6-FLUOR-1, A-DIGIDE
    ro-A-oxo-1,8-naphthydrin-3-carboxylic acid. Get 1-β-cyclopropyl-7- (1,4-diazabicyclo 3, 2,1} oct-yl) -6-fluoro-1, -dihydro-4-oxo-1,8-naphthydrin-3-carboxylic hydrochloride acids with t, pl. - 300 ° C (decomposition).
    Example
    ABOUT

    / l
    Example 1 is repeated, starting from 1-α-ethyl-6,7,8-trifluoro-1, A-dihydro-α-oxo 3 quinolinecarboxylic acid. The hydrochloride of 7 (1, 4-diazabicyclo 3,2,) - 1-ethyl-6,8-difluoro-1, 4-dihydro-oxo-3-quinoline carboxylic acid with m.p. 308-ЗТ2 ° С (decomposition).
    Example 8
    About HCH HGG-COOH
     / uU XHCI 4 skLsnz
    To a mixture of 2.8 g (10 mmol) 9, U-difluoro-2,3-dihydro-3-methyl, 7 oxo-7H15-diazabicyclo 3, 2.1 oct-4-yl) -6.8- - difluoro -1 - (-fluorophenyl) -1, A -dihydro-β- -oxo-3-quinolinecarboxylic acid, m.p. "SJ-31 ° C (decomposition)" Example 10.
    20О
    25
    N © N
    To 2.0 g (6 mmol) 7 chloro-1-cycloprop opil-6-fluoro-1,4-dihydro-8-nitro-oxo-3-quinoline-carboxylic acid in a mixture of 10 ml of acetonitrile and 25 ml 30 dimethylformamide add 0.7 g
    (6 mmol) 1, -diazabicyclo 2, 2.2 octane and 0.7 g (6 mmol) 1,4-diazabicyclo, 1j octane and heated under reflux for 2 hours
    - pyrido 1,2, 1,4 benzoxazin-6-. Then it is concentrated and water is added. Ox-carboxylic acid and 1.2 g (10.7 mmol) of 1, -diazabicyclo 3, 2.1-octane in 25 ml of dimethyl sulfoxide were added 2.2 g (20 mmol) of 1, -diazabicyclo 2.2.2 octane and warm for 5 h at 120 ° C. The mixture is concentrated in vacuo, the residue is mixed with 0 ml of acetonitrile, the insoluble residue is filtered off with suction and purified by chromatography on silica gel using dichloromethane, methanol and a 20% ammonia solution in a ratio of 2: 4: 1 as a diluent. 1.2 g of solid product is recovered, which, by dissolving in 8 ml of half-concentrated hydrochloric acid and precipitating with 30 ml of ethanol, is transferred to the hydrochloride. Yield: 1.1 g of 10- (1,4-diazabicyclo 3,2,1 oct -4-yl) -I-fluorine-2,3 -dihydride - ro-3 methyl-7-oxo-7H- hydrochloride pyrido 1,2,3-de 1,4-benzoxazine-6-carboxylic acid, so pl. 355 ° C (decomposition). Starting from 290 ° C, the hydrochloride becomes darker.
    ice, allowed to crystallize, sucked off, washed with water and dried. Yield: 1 g H1% theory of 1-cyclopropyl-7 (1, -diazabicyclo-40, 1 oct-4-yl) -6-fluoro-1, -dihydro-8-nitro-4-oxo-3-quinolinecarbono - howl acid, so pl. 215 232 ° C (decomposition).
    Example
    eleven
    45
    50
    CH2-X
    Cun
    55
    530 mg (2 mmol) of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-oxo-3-xi-nolin-carboxylic acid in C ml of acetonitrile and 6 ml of dimethylformamide together with 530 mg (2 mmol) of 2- benzyl-2,5-diazabicyclo 2,2,1J heptane-dihydrochloride and 880 mg (7.9 mmol) 1,4-diazabicyclo 2,2,2 octane for j
    Example
    soon
    J
    HC1
    Example 1 is repeated, starting with 6, 7,8-trifluoro-1 - (- fluorophenyl) -1, k-dihydro-oxo-3-quinolinecarboxylic acid. Get hydrochloride 7 (1,
    -diazabicyclo 3, 2.1 oct-4-yl) -6,8- -difluor -1 - (-fluorophenyl) -1, A-di-di-β- - oxo-3-quinolinecarboxylic acid, mp 31 ° C (decomposition) o Example 10.
    ABOUT
    25
    N © N
    To 2.0 g (6 mmol) 7 chloro-1-cycloprop opil-6-fluoro-1,4-dihydro-8-nitro-oxo-3-quinoline-carboxylic acid in a mixture of 10 ml of acetonitrile and 25 ml dimethylformamide added 0.7 g
    (6 mmol) 1, -diazabicyclo 2, 2.2 octane and 0.7 g (6 mmol) 1,4-diazabicyclo, 1j octane and heated under reflux for 2 hours
    Then it is concentrated and water is added. Chilled with ice, allowed to crystallize, sucked off, washed with water and dried. Output: 1 g I1% of theory) 1-cyclopropyl-7 (1, -diazabicyclo-0, 1 oct-4-yl) -6-fluoro-1, -dihydro-8-nitro-4-oxo-3- quinoline carboxylic acid, m.p. 215 232 ° C (decomposition).
    Example
    eleven
    45
    Cun
    50
    CH2-X
    530 mg (2 mmol) of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-oxo-3-xi-nolin-carboxylic acid in C ml of acetonitrile and 6 ml of dimethylformamide together with 530 mg (2 mmol) of 2- benzyl-2,5-diazabicyclo 2,2,1J heptane-dihydrochloride and 880 mg (7.9 mmol) 1,4-diazabicyclo 2,2,2 octane for j
    6 hours warm with reflux. The reaction mixture is concentrated, the residue is stirred with water, the precipitate is filtered off with suction, washed with water and dried. The resulting crude product (0.8 g with m „melting point 194–205 ° C, decomposition) is purified by chromatography on 60 g of silica gel using dichloromethane, methanol and ammonium hydroxide as a diluent in a ratio of 150: 40: 1 . This gives 0.67 g (66% of theory) of 7- (5 benzyl-2.5-Diaza-bicyclo 2.2, l hept-2-yl) -1-cyclopropyl-b-ftbr-1,4- dihydro-4 oxo-3 -quinolinecarboxylic acid, so pl. 205-21 0 (decomposition). Example 12
    Cun
    HЈ-NЈ
    Example 11 is repeated, starting from 8-methyl-3,8-diazabicyclo 3,2,1} octane dihydrochloride, and the crude product is recrystallized from glycol monomethyl ether. Get 1-cyclopropyl-6-fluoro-1, 4-dihydro 7 (8-methyl-3,8-diazabicyclo 3,2,1 oct-3-yl-4-oxo-3-quinolinecarboxylic acid, so pl 273-278 ° С (decomposition) about 13.

    Example
    Cun
    HC1
    Example 1 is repeated, starting from 5-methyl-1,4-diazabicyclo 3,2,1 octa40 azabicyclo 2.2.2 octane and 2.1 g, (17 mmol) 2-methyl-1,4-diazabicyclo 3 , 2, lJ. Octane, and heated for 6 hours under reflux. The mixture is evaporated, water is added to the residue.
    on. 1-cyclro-45 hydrochloride (pH 7) is obtained., Undissolved crystals from saw-6-fluoro-1, 4-dihydro-7 (5-methyl--1,4-diaza bicyclic about 3.2, oct-4 -yl) -4-oxo-3-quinolinecarboxylic acid with mp. C (decomposition). Example 14
    ABOUT
    -soon
    sucked, washed with water and recrystallized from glycol monomethyl ether. Get T, 4 g of 1-cyclopropyl-6-fluoro-1,4-dihydro-7-50 - (2-methyl-1,4-diazabicyclo 3,2,1j oct-4-yl) -4-oxo-3 quinolinecarboxylic acid with so pl. 255-257 0 (decomposition).
    J
    xHCl
    Example 1 is repeated, starting with 6.7 8-trifluoro-1- (2,4-difluorophenyl) -1,4-di-hydro-4-oxo 3 quinoline-carboxylic acid to obtain hydrochloride 7 (-diazabicyclo 3,2,1 Oct-4-yl) -6,8- -difluoro-1 - (2,4-difluorophenyl) -1,4-di-hydro-4-oxo-3-quinolinecarboxylic acid, m.p. 329 331 ° C (decomposition).
    Example 15 °
    Cun
    s
    DN
    xHCl
    Example 1 is repeated, starting with 6,7, 8-trifluoro-1,4-dihydro-1-methylamino-4-oxo-3-quinolinecarboxylic acid. Hydrochloride, -diazabicyclo 3,2,1 oct-4-yl) -6,8-difluoro--1, -methylamino-oxo-3 quinolinecarboxylic acid with m.p. 329-331 ° C
    (decomposition). Example
    Cun
    CH3
    To 2.65 g (10 mmol) of 1-cycloprolyl-6,7-Difluoro-1,4-dihydro-4-ocean-3-quinoline kaonic acid in 20 ml of acetonitrile and 10 ml of dimethylformamide are added 2, 7 g (24 mmol) 1,4-diazabicyclo 2.2.2 octane and 2.1 g, (17 mmol) 2-methyl-1,4-diazabicyclo-3,2, lJ. Octane, and for 6 h heated to reflux. The mixture is evaporated, water is added to the residue.
    (pH 7)., undissolved crystals are sucked off, washed with water and recrystallized from glycol monomethyl ether. Get T, 4 g of 1-cyclopropyl-6-fluoro-1,4-dihydro-7- - (2-methyl-1,4-diazabicyclo 3,2,1j oct-4-yl) -4-oxo-3 quinolinecarboxylic acids with so pl. 255-257 0 (decomposition).
    Example 17
    55
    Cun
    Example 16 is repeated, starting from 3-oxa-8-aza-bicyclo-3,2,1 octane hydrochloride. Get 1-cyclopropyl-b-fluoro-1, -dihydro-7- (3 oxo-8-aza-bicyclo 3,2,1 oct-8-yl) -4-ox-3-quinoline-carboxylic acid with t .pl. 283-28 ° C, decomposition (of glycol monomethyl ether).
    Example 19
    soon
    N © N H3C CH,
    Example 16 is repeated, starting with 2, 2-dimethyl-1, -diazabicycloses, 2.1J octane. Obtain 1 4-cyclopropyl-6-α-fluoro-1,1-dihydro-7- (2,2-dimethyl-1, - diazabicyclo 3, 2.1 oct-1-yl) co-3-quinolinecarboxylic acid with m.p. . 2A2-2A6 ° C (decomposition). Example 20
    Cun
    HC1
    To 3.37 g (10 mmol) of 6,7,8-trifluoro--1 - (- fluorophenyl) -1, -dihydro-4-oxo-3-quinolinecarboxylic acid in 30 ml of dimethyl sulfoxide was added 2.7 g (2 mmol) 1, -diazabicyclo 2,2.2 octane and 2.1 g (17 mmol) 2-methyl--1, A-diazabicyclo3, 2, l octane and heated to for 2 h. Ras20
    0
    3.5 g (10 mmol) of 6,7,8-trifluoro-1- (2,4-difluoro-phenyl) -1,4-dihydro-ox-with-3-quinolinecarboxylic acid in 30 ml of dimethyl sulfoxide together with 2.7 g (2 mmol) of 1, -diazabicyclo, 2 octane and 2.1 g (17 mmol) of 2- -methyl-1, -diazabicycle 3.2, lJ of octane are heated for 2 h. After being recrystallized from water, 5 g of 6,8-difluoro--1- (2, -difluorophenyl) -1, -dihydro-7- - (2-methyl-1, - diazabicyclo 3, 2.1 oct - -yl) -4-oxo-3-chi ncarboxylic acid with so pl. 278-280 ° C (decomposition).
    Example 22
    Cun
    45
    Example 16 is repeated, starting with 2.8 g (10 mmol) of 1-cyclopropyl-b, 7, 8-trifluoro-1,4-dihydro-oxo-3-quinoline-carboxylic acid. 1.3 g of 1-cyclopropyl-b, 8-difluoro-1, -di-di- (2-methyl-1,4-diazabicyclo 3,2,1J) -k-oxo-3-quinolinecarboxylic acid with m.p. 239-2 2 ° С, decomposition (from glycol monomethyl ether).
    eleven
    The compound ethyl ester 1-cyclopropyl-7- (1, A-diazabicyclo 3, ij oct-4-yl) -6,8-difluoro-G, 4-dihydro-oxo-3- quinolinecarboxylic acid with so pl. 19b-199 C (example 23).
    Biological experience. Determination of the minimum inhibition concentration
    (mkt).
     Solutions of the studied compounds of various concentrations are mixed with a liquid agar medium and poured into cups, after which the plates are infected with the bacteria indicated in the table. This determines the concentration of the test compound that inhibits the formation of visible colonies of bacteria for 2 hours.
    The tested compounds, bacteria and the results of the experiment are tabulated.
    A known antibacterial agent, 1-ethyl-6-fluoro-1, -dihydro-ox-with-O-Diazabicyclo non-) -yl-3-quinoline-carboxylic acid, was used as a comparison (patent of the USSR No. 40281 2 / 04, cl. 07 D 487/18, 18.09.85.
    As can be seen from the table, new derivatives of quinoline- or naphthyridinecarboxylic acid, as compared with the structural analogue, have improved antibacterial activity.
    权利要求:
    Claims (1)
    [1]
    Invention Formula
    The method of obtaining quinoline- or naphthyridinecarboxylic acid derivatives of general formula 40
    Xiv vVCOOR2
    jЈT Y
    D) HCH S
    "3 a n
    Al
    R (- ethyl, cyclopropyl, methylamino, A-fluorophenyl, 2, A-difluorophenyl;
    R is hydrogen, ethyl;
    R, - in the ring system, an unsubstituted or one or two methyl-substituted radical of the formula
    ten
    5 20
    889712
    1III I
    N NN N I
    IIв
    B c
    where R4 is methyl or benzyl; X4 - fluorine or nitro; A is a nitrogen atom or C-R5, where Rf is hydrogen, fluorine, chlorine or a nitro group, or together with R, can form a bridge having the structure -0-CHt-CH-CH3,
    moreover, if X is fluorine, R is hydrogen and A is CF or N, R is ethyl or cyclopropyl, or RJJ with R, forms a bridge with the structure —0 — CH2 — CH — CHg, then RJ cannot mean radical
    VN (N or, if X, is fluorine, Rj. Hydrogen, A - -CH-, CC1, CF, or together with RJ can form a bridge having the structure -0-CHG-CH-CH3, then R3 cannot mean
    CHS-N) N- or SNC-X to-,
    or their acid addition salts or their hydrates, characterized in that the compound of the general formula
    About XlYVVCOOR
    h a
    N hi
    five
    0
    where R., R2, X, and A have the indicated meanings;
    Hg-halogen
    subjected to interaction with the compound of the General formula
    R3h
    where R.J has the indicated values, or with its hydro- or dihydrochloride, if necessary in the presence of an acid binding agent, followed by isolation of the desired product in free form or as acid addition salts or their hydrates.
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    同族专利:
    公开号 | 公开日
    KR870007176A|1987-08-17|
    FI870200A0|1987-01-19|
    PL263735A1|1988-07-21|
    ZA87380B|1987-09-30|
    JPS62169789A|1987-07-25|
    HUT45531A|1988-07-28|
    DK29287A|1987-07-22|
    NO870126L|1987-07-22|
    IL81291D0|1987-08-31|
    FI870200A|1987-07-22|
    PT84135A|1987-02-01|
    NO870126D0|1987-01-13|
    DK29287D0|1987-01-20|
    DE3601567A1|1987-07-23|
    AU6746387A|1987-07-23|
    CN87100354A|1987-09-02|
    EP0230274A2|1987-07-29|
    EP0230274A3|1988-03-09|
    DD265401A5|1989-03-01|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US6184380B1|1999-01-25|2001-02-06|Pfizer Inc.|Process for preparing naphthyridones and intermediates|
    US7019142B2|1998-01-16|2006-03-28|Pfizer Inc.|Process for preparing naphthyridones and intermediates|US3281423A|1964-02-03|1966-10-25|Merck & Co Inc|1, 3-ethanopiperazines and process|
    EP0090424B1|1982-03-31|1986-05-28|Sterling Drug Inc.|New quinolone compounds and preparation thereof|
    NZ208470A|1983-07-18|1988-06-30|Abbott Lab|6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid derivatives and antibacterial compositions containing such|
    IL74244A|1984-02-17|1988-06-30|Warner Lambert Co|Quinoline derivatives,their preparation and pharmaceutical compositions containing them|
    US4571396A|1984-04-16|1986-02-18|Warner-Lambert Company|Antibacterial agents|
    IN166416B|1985-09-18|1990-05-05|Pfizer|IL83049A|1986-07-04|1991-12-12|Chemie Linz Ag|4-quinolinone-3-carboxylic acid derivatives,their manufacture and pharmaceutical compositions containing them|
    ZA877471B|1986-10-08|1988-04-05|Bristol-Myers Company|1-tertiary-alkyl-substituted naphthyridine-and quinoline-carboxylic acid antibacterial agents|
    WO1989000158A1|1987-07-02|1989-01-12|Pfizer Inc.|Bridged-diazabicycloalkyl quinolone carboxylic acids and esters|
    US4992546A|1987-07-31|1991-02-12|Warner-Lambert Company|Process for preparing 6,8-diazabicyclo[3.2.2]nonane derivatives|
    US4923879A|1987-07-31|1990-05-08|Warner-Lambert Company|1,8-Naphthyridines and their use as antibacterial agents|
    US4968799A|1987-07-31|1990-11-06|Warner-Lambert Company|Antibacterial agents|
    JPH0588714B2|1988-04-23|1993-12-24|Toyama Chemical Co Ltd|
    KR910003630B1|1988-06-17|1991-06-07|한국과학기술원|Benzoyl acetic ester derivatives and there of method|
    DE3910663A1|1989-04-03|1990-10-04|Bayer Ag|5-ALKYLCHINOLON CARBONIC ACIDS|
    US5385913A|1989-10-06|1995-01-31|Pfizer Inc.|1,4-dihydro-4-oxo-3-quinoline derivatives as selectively toxic mammalian antibacterial agents|
    WO1991004972A1|1989-10-06|1991-04-18|Pfizer Inc.|1,4-dihydro-4-oxo-3-quinoline derivatives as selectively toxic mammalian antibacterial agents|
    FR2656611B1|1990-01-04|1992-05-07|Hoechst France|NEW QUINOLONES, THEIR SALTS, USEFUL AS ANTIMICROBIAL AGENTS, PREPARATION METHOD AND THEIR APPLICATION AS MEDICAMENTS AND COMPOSITIONS CONTAINING THEM.|
    DE19546249A1|1995-12-12|1997-06-19|Bayer Ag|New crystal modification of 1-cyclopropyl-7 --6-fluoro-1,4-dihydro-8-methoxy-4 -oxo-3-quinoline carboxylic acid hydrochloride , process for its preparation and pharmaceutical preparations containing it|
    SE0003795D0|2000-10-20|2000-10-20|Astrazeneca Ab|Pharmaceutically useful compounds|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    DE19863601567|DE3601567A1|1986-01-21|1986-01-21|7--CHINOLONCARBONIC ACID AND -NAPHTHYRIDON-CARBONIC ACID DERIVATIVES|
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