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KR870007129A - 항균제로써 퀴놀린-3-카복실산의 개량된 제조 방법 - Google Patents

항균제로써 퀴놀린-3-카복실산의 개량된 제조 방법 Download PDF

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KR870007129A
KR870007129A KR1019870000127A KR870000127A KR870007129A KR 870007129 A KR870007129 A KR 870007129A KR 1019870000127 A KR1019870000127 A KR 1019870000127A KR 870000127 A KR870000127 A KR 870000127A KR 870007129 A KR870007129 A KR 870007129A
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cyclopropyl
difluoro
dihydro
oxo
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엔.웸플 제임스
엔. 웸플 제임스
알.젤러 제임스
알. 젤러 제임스
엠.도마갈라 존
엠. 도마갈라 존
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워너-람버트 캄퍼니
크리스틴 에이. 트라우트웨인
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    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
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Abstract

내용 없음

Description

항균제로써 퀴놀린-3-카복실산의 개량된 제조 방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (28)

  1. (a)염화 2,3,4,5-테트라플루오로벤조일을 최소한 1 당량의 염기 존재하에 삼차-부틸 시아노아세테이트와 반응시키고 산 처리 후 일반식 (2)의 화합물을 얻고 :
    (b) 일반식(2)의 화합물을 환류시키면서 트리에틸오르토포름에이트 또는 트리메틸오르토포름에이트 및 무수 아세트산으로 처리한 다음, 식중 R2가 C1-3알킬 또는 C3-6사이클로알킬인 일반식 R2NH2의 0.8-1.2 당량의 아민으로 주변 온도에서 처리하고, 최소한 1 당량의 삼차 아민 염기의 존재하에 극성 중성 용매내에 환류시키면서 가열하여 일반식 (3)의 화합물을 얻고 ;
    (c) 일반식 (3)의 상기 화합물을 A가 치환된 아미노 그룹인 최소한 1 당량의 치환된 아민과 반응시킨 다음 산 가수분해시켜 다음 일반식 (1)의 제약학적으로 허용 가능한 산 부가염을 얻고, 원한다면 공지된 방법으로 상기 화합물을 당해 유리산 또는 제약학적으로 허용 가능한 당해 염기염으로 전환시키는 것으로 구성되는 일반식(1)의 화합물 및 제약학적으로 허용 가능한 당해 산 부가염 또는 염기염의 제조 방법.
    식중, A는 치환된 아미노 그룹,
    R2는 C1-3알킬 또는 C3-6사이클로알킬.
  2. 제 1 항에 있어서, 단계(b)에 사용된 삼차 아민이 트리에틸아민인 방법.
  3. 제 1 항에 있어서, 극성 중성 용매가 디메틸설폭사이드인 방법.
  4. 제 1 항에 있어서, 단계(c)의 산 가수분해를 120-150℃에서 농염산과 가열함으로써 행하는 방법.
  5. 식중 R2가 C1-3알킬 또는 C3-6사이클로알킬인 다음 일반식의 화합물을
    최소한 1 당량의 A가 치환된 아미노 그룹인 치환된 아민 A-H과 반응시킨 다음 산 가수분해시키고, 원한다면 결과의 제약학적으로 허용 가능한 산 부가염을 공지된 방법으로 당해 유리산 또는 제약학적으로 허용 가능한 당해 염기염으로 전환시키는 것으로 구성되는 다음 일반식의 화합물 및 제약학적으로 허용가능한 당해 산 부가염 또는 염기염의 제조 방법.
    식중, A는 치환된 아미노 그룹,
    R2는 C1-3알킬 또는 C3-6사이클로알킬.
  6. 다음 일반식의 화합물.
    [식중, R2는 C1-3알킬 또는 C3-6사이클로알킬.
  7. 제 6 항에 있어서, R2가 사이클로프로필인 화합물.
  8. 제 5 항에 있어서, A가 5 또는 6원의 복소환식 아미노 그룹으로, 환이 알킬은 C1-3이고 R3는 수소 또는 C1-4알킬인 N-R3에 의해 중절되고 C1-3알킬아미노, 메틸아미노, 에틸아미노, 알킬아미노, 알킬아미노에틸, 또는 알킬아미노메틸에 의해 치환될 수 있는 방법.
  9. 제 5 항에 있어서, A가 피페라진, N-메틸피페라진 또는 식중 n"가 0또는 1이고 R3'가 수소, 메틸, 에틸, 1-또는 2-프로필인 다음 일반식의 피롤리딘의 방법.
  10. 제 5 항에 있어서, A가 식중 R3'가 수소, 메틸, 에틸, 1-또는 2-프로필인 다음 일반식인 방법.
  11. 제 5 항에 있어서, A가 식중 R이 수소, 메틸, 에틸, 1-또는 2-프로필, 하이드록시에틸, 벤질, 또는 p-아미노벤질이고 R'가 수소 또는 아세틸인 다음 일반식의 방법.
  12. 제 5 항에 있어서, 7-[3-(아미노 메틸)-1-피롤리디닐]-1-사이클로프로필-6,8-디플루오로-1,4-디하이드로-4-옥소-3-퀴놀린카복실산의 제조 방법.
  13. 제 5 항에 있어서, 1-사이클로프로필-7-[3-(에틸아미노)메틸]-1-피롤리디닐]-6,8-디플루오로-1,4-디하이드로-4-옥소-3-퀴놀린카복실산의 제조 방법.
  14. 제 5 항에 있어서, 7-[3-아미노-1-피롤리디닐]-1-사이클로프로필-6,8-디플루오로-1,4-디하이드로-4-옥소-3-퀴놀린카복실산의 제조 방법.
  15. 제 5 항에 있어서, 1-사이클로프로필-6,8-디플루오로-1,4-디하이드로-7-[3-(메틸아미노)메틸]-1-피롤리디닐]-4-옥소-3-퀴놀린카복실산의 제조 방법.
  16. 제 5 항에 있어서, 1-사이클로프로필-7-[3-(에틸아미노)-1-피롤리디닐]-6,8-디플루오로-1,4-디하이드로-4-옥소-3-퀴놀린카복실산의 제조 방법.
  17. 제 5 항에 있어서, 1-사이클로프로필-6,8-디플루오로-1,4-디하이드로-7-[3-[[(1-메틸에틸)아미노]메틸]-1-피롤리디닐]-4-옥소-3-퀴놀린카복실산의 제조 방법.
  18. 제 5 항에 있어서, 7-(2,5-디아자바이사이클로[2.2.2]옥트-2-일)-1-사이클로프로필-6,8-디플루오로-1,4-디하이드로-4-옥소-3-퀴놀린카복실산의 제조 방법.
  19. 제 5 항에 있어서, 7-[3-(엑소-아미노)-8-아자바이사이클로[3.2.1] 옥트-8-일]-1-사이클로프로필-6,8-디플루오로-1,4-디하이드로-4-옥소-3-퀴놀린카복실산의 제조 방법.
  20. 제 5 항에 있어서, 7-(1,4-디아자바이사이클로[3.2.1] 옥트-4-일)-1-사이클로프로필-6,8-디플루오로-1,4-디하이드로-4-옥소-3-퀴놀린카복실산의 제조 방법.
  21. 제 5 항에 있어서, 1-사이클로프로필-6,8-디플루오로-1,4-디하이드로-7-(5-메틸-2,5-디아자비사이클로[2.2.1] 헵트-2-일)-4-옥소-3-퀴놀린카복실산의 제조 방법.
  22. 제 1 항에 있어서, 1-사이클로프로필-7-(2,5-디아자바이사이클로 [2.2.1] 헵트-2-일)-6,8-디플루오로-1,4-디하이드로-4-옥소-퀴놀린카복실산의 제조 방법.
  23. 제 5 항에 있어서, 1-에틸-7-[3-(에틸아미노)메틸]-1-피롤리디닐]-6,8-디플루오로-1,4-디하이드로-4-옥소-3-퀴놀린카복실산의 제조 방법.
  24. 식중 R이 CN 또는 COOR'(R'는 C1-6알킬 또는 아랄킬)이고 R2가 C1-3알킬 또는 C3-6사이클로알킬인 다음 일반식의 화합물을 최소한 1 당량의 삼차 아민의 존재하에 극성 중성
    용매내에서 환류시키면서 가열하는 것으로 구성되는 다음 일반식의 화합물의 제조 방법.
    식중, R은 CN 또는 COOR'(R'는 C1-6알킬 또는 아랄킬).
    R2는 C1-3알킬 또는 C3-6사이클로알킬.
  25. 제24항에 있어서, 삼차 아민이 트리에틸아민인 방법.
  26. 제24항에 있어서, 극성 중성 용매가 디메틸설폭사이드인 방법.
  27. 제24항에 있어서, R이 CN 또는 COOR'(R'는 메틸, 에틸 또는 벤질)인 방법.
  28. 제24항에 있어서, R2가 사이클로프로필인 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019870000127A 1986-01-13 1987-01-10 항균제로써 퀴놀린-3-카복실산의 개량된 제조방법 Expired KR900001176B1 (ko)

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US818,450 1986-01-13
US06/818,450 US4772706A (en) 1986-01-13 1986-01-13 Process for quinoline-3-carboxylic acid antibacterial agents

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KR870007129A true KR870007129A (ko) 1987-08-17
KR900001176B1 KR900001176B1 (ko) 1990-02-27

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US (1) US4772706A (ko)
EP (1) EP0236673B1 (ko)
JP (1) JPS62167769A (ko)
KR (1) KR900001176B1 (ko)
CN (1) CN87100298A (ko)
AT (1) ATE108441T1 (ko)
AU (1) AU587885B2 (ko)
CA (1) CA1283658C (ko)
DE (1) DE3750187T2 (ko)
DK (2) DK9687A (ko)
ES (1) ES2056048T3 (ko)
FI (1) FI88614C (ko)
HU (2) HU204258B (ko)
IE (1) IE59538B1 (ko)
IL (1) IL81144A (ko)
NO (1) NO175366C (ko)
NZ (1) NZ218864A (ko)
OA (1) OA08460A (ko)
PT (1) PT84092B (ko)
ZA (1) ZA869689B (ko)

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IN166416B (ko) * 1985-09-18 1990-05-05 Pfizer
ZA877471B (en) * 1986-10-08 1988-04-05 Bristol-Myers Company 1-tertiary-alkyl-substituted naphthyridine-and quinoline-carboxylic acid antibacterial agents
US4933335A (en) * 1987-08-07 1990-06-12 Warner-Lambert Company Quinolones as antibacterial agents
US4920120A (en) * 1988-01-25 1990-04-24 Warner-Lambert Company Antibacterial agents
US5585491A (en) * 1988-01-25 1996-12-17 Otsuka Pharmaceutical Co., Ltd. Antibacterial agents
US5233091A (en) * 1988-06-21 1993-08-03 Pfizer Inc. 6-fluoro-1,4-dihydroquinol-4-one-3-carboxylic acid derivatives and intermediates therefor
US5103040A (en) * 1988-06-21 1992-04-07 Pfizer Inc. 6-fluoro-1,4-dihydroquinol-4-one-3-carboxylic acid derivatives and intermediates therefor
US5104868A (en) * 1988-06-21 1992-04-14 Pfizer Inc. Tricyclic derivatives of 7-substituted-6-fluoro-1,4-dihydroquinol-4-one-3-carboxylic acids and esters
US5039682A (en) * 1988-06-21 1991-08-13 Pfizer Inc. 6-fluoro-1,4-dihydroquinol-4-one-3-carboxylic acid derivatives and intermediates therefor
DE3906365A1 (de) * 1988-07-15 1990-01-18 Bayer Ag 7-(1-pyrrolidinyl)-3-chinolon- und -naphthyridoncarbonsaeure-derivate, verfahren sowie substituierte (oxa)diazabicyclooctane und -nonane als zwischenprodukte zu ihrer herstellung, und sie enthaltende antibakterielle mittel und futterzusatzstoffe
ES2036136B1 (es) * 1991-10-16 1994-03-01 Inke Sa Procedimiento para la obtencion del acido 1-(2,4-difluorofenil)-6-fluoro-7-(3-metilpiperacinil)-4-oxo-1, 4-dihidroquinolin-3-carboxilico y sus sales.
WO2006052889A2 (en) * 2004-11-05 2006-05-18 Theravance, Inc. Quinolinone-carboxamide compounds
EP1807422B1 (en) * 2004-11-05 2009-09-02 Theravance, Inc. 5-ht4 receptor agonist compounds
ES2427247T3 (es) 2006-03-13 2013-10-30 Kyorin Pharmaceutical Co., Ltd. Aminoquinolonas como inhibidores de GSK-3
EP2203458B1 (en) 2007-09-11 2011-11-02 Kyorin Pharmaceutical Co., Ltd. Cyanoaminoquinolones as gsk-3 inhibitors
CN101855229A (zh) 2007-09-12 2010-10-06 埃迪威克斯生物科学公司 作为gsk-3抑制剂的螺环状氨基喹诺酮
BRPI1008974A2 (pt) 2009-03-11 2017-06-06 Kyorin Seiyaku Kk composto, composição farmacêutica, e, método para tratar, prevenir ou melhorar uma doença mediada com gsk-3
CN107602465A (zh) * 2016-07-12 2018-01-19 重庆大学 一种喹诺酮类衍生物及其应用

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HU167910B (ko) * 1972-11-22 1976-01-28
DE3142854A1 (de) * 1981-10-29 1983-05-11 Bayer Ag, 5090 Leverkusen 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7-piperazino-chinolin-3-carbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel
IE55898B1 (en) * 1982-09-09 1991-02-14 Warner Lambert Co Antibacterial agents
DE3318145A1 (de) * 1983-05-18 1984-11-22 Bayer Ag, 5090 Leverkusen 7-amino-1-cyclopropyl-6,8-difluor-1,4-dihydro-4-oxo-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel
JPS60123837A (ja) * 1983-12-09 1985-07-02 Mitsubishi Paper Mills Ltd ハロゲン化銀写真乳剤
DE3420116A1 (de) * 1984-05-30 1985-12-05 Bayer Ag, 5090 Leverkusen Immunstimulierende mittel
DE3426486A1 (de) * 1984-07-18 1986-01-30 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung von chinolon- und naphthyridoncarbonsaeuren
DE3426483A1 (de) * 1984-07-18 1986-01-30 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung von halogenierten chinoloncarbonsaeuren
DE3502935A1 (de) * 1984-09-29 1986-04-10 Bayer Ag, 5090 Leverkusen 3-amino-2-benzoyl-acrylsaeurederivate und ein verfahren zu ihrer herstellung

Also Published As

Publication number Publication date
IL81144A0 (en) 1987-08-31
DK74994A (da) 1994-06-23
HU197324B (en) 1989-03-28
CA1283658C (en) 1991-04-30
PT84092A (en) 1987-02-01
JPS62167769A (ja) 1987-07-24
ZA869689B (en) 1988-08-31
DK9687A (da) 1987-07-14
AU6695486A (en) 1987-07-16
IE870018L (en) 1987-07-13
CN87100298A (zh) 1987-08-19
NZ218864A (en) 1989-02-24
FI88614C (fi) 1993-06-10
KR900001176B1 (ko) 1990-02-27
EP0236673A3 (en) 1988-08-31
ES2056048T3 (es) 1994-10-01
IL81144A (en) 1990-12-23
DK9687D0 (da) 1987-01-09
AU587885B2 (en) 1989-08-31
EP0236673A2 (en) 1987-09-16
PT84092B (pt) 1989-05-31
OA08460A (en) 1988-07-29
ATE108441T1 (de) 1994-07-15
NO175366C (no) 1994-10-05
NO175366B (no) 1994-06-27
US4772706A (en) 1988-09-20
FI88614B (fi) 1993-02-26
EP0236673B1 (en) 1994-07-13
NO870109L (no) 1987-07-14
HUT44513A (en) 1988-03-28
DE3750187T2 (de) 1994-11-10
FI870086A0 (fi) 1987-01-09
HU204258B (en) 1991-12-30
NO870109D0 (no) 1987-01-12
HUT46671A (en) 1988-11-28
IE59538B1 (en) 1994-03-09
DE3750187D1 (de) 1994-08-18
FI870086L (fi) 1987-07-14

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