KR870007171A - 6,7-디히드로-5,8-디메틸-9-플루오로-1-옥소-1H,5H-벤조[i,j] 퀴놀리진-2-카르복실산의 제조방법 - Google Patents

6,7-디히드로-5,8-디메틸-9-플루오로-1-옥소-1H,5H-벤조[i,j] 퀴놀리진-2-카르복실산의 제조방법 Download PDF

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KR870007171A
KR870007171A KR870000434A KR870000434A KR870007171A KR 870007171 A KR870007171 A KR 870007171A KR 870000434 A KR870000434 A KR 870000434A KR 870000434 A KR870000434 A KR 870000434A KR 870007171 A KR870007171 A KR 870007171A
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South Korea
Prior art keywords
fluoro
dimethyl
benzo
dihydro
oxo
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KR870000434A
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English (en)
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KR900005656B1 (en
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얼 윌리암스 브루스
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더블유 지 미리디스
라이커 라보러토리즈, 인코포레이티드
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Publication of KR870007171A publication Critical patent/KR870007171A/ko
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/18—Halogen atoms or nitro radicals

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Quinoline Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

내용 없음

Description

6,7-디히드로-5,8-디메틸-9-플루오로-1-옥소-1H,5H-벤조〔i,j〕퀴놀리진-2-카르복실산의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (3)

1) 6-플루오로-2-메틸 퀴놀린(Ⅱ)과 브롬을 반응시켜 5-브로모-6-플루오로-2-메틸 퀴놀린(Ⅲ)을 제조하고 ;
2) 디클로로〔1,3-비스(디페닐포스피노)프로판〕니켈〔Ⅱ〕의 존재하에 메틸 그리나드 시약을 5-브로모-6-플루오로-2-메틸 퀴놀린과 반응시켜 2,5-디메틸-6-플루오로 퀴놀린(Ⅳ)을 제조하고,
3) 식(Ⅳ)의 2,5-디메틸-6-플루오로 퀴놀린을 환원시켜 2,5-디메틸-6-플루오로-1,2,3,4-테트라하이드로 퀴놀린(Ⅴ)을 제조하고 ;
4) 식(Ⅴ)의 2,5-디메틸-6-플루오로-1,2,3,4-테트라하이드로 퀴놀린을 식(ⅤA)의 알콕시 메틸렌말론산의 디에스테르로서 축합하여 2-(N 테트라하이드로 퀴놀리닐)메틸렌 말론산을 제조하고.
5) 2-(N-테트라 하이드로 퀴놀리닐)메틸렌 말론산을 고리닫힘시켜 6,7-디히드로-5,8-디메틸-9-플루오로-1-옥소-1H,5H-벤조〔i,j〕퀴놀리진-2-카르복실산(Ⅶ)의 에스테르를 제조하고,
6) 에스테르를 가수분해하여 6,7-디히드로-5,8-디메틸-9-플루오로-1-옥소-1H,5H-벤조〔i,j〕퀴놀리진-2-카르복실산(Ⅰ)을 제조하는 것으로 구성된 하기식(Ⅰ)의 6,7-디히드로-5,8-디메틸-9-플루오로-1-옥소-1H,5H-벤조〔i,j〕퀴놀리진-2-카르복실산의 제조방법.
상기식에서
alk는 1-4개의 탄소를 함유하는 알킬을 뜻하며 각각의 R1는 독립적으로 1내지 약 4개의 탄소 원자의 알킬 또는 R1는 함께 이소프로필 라디칼을 형성)
디클로로〔1,3-비스(디페닐 포스피노)프로판〕니켈〔Ⅱ〕의 존재하에 메틸 그리나드 시약과 5-브로모-6-플루오로 메틸퀴놀린을 반응시키는 것으로 구성된 방법.
제2항에 있어서, 그다음 단계로 상기 2,5-디메틸-6-플루오로 퀴놀린을 2,5-디메틸-6-플루오로-1,2,3,4-테트라하이드로 퀴놀린으로 환원시키는 단계가 구성된 제조방법.
※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR8700434A 1986-01-22 1987-01-21 Process for 6,7- dihydro -5,8- dimethyl-9-fluoro - 1-oxo- 1h, 5h - benzo (i,i) quinolizine-2-carboxylic acid KR900005656B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US82104886A 1986-01-22 1986-01-22
US821048 1986-01-22

Publications (2)

Publication Number Publication Date
KR870007171A true KR870007171A (ko) 1987-08-17
KR900005656B1 KR900005656B1 (en) 1990-08-03

Family

ID=25232365

Family Applications (1)

Application Number Title Priority Date Filing Date
KR8700434A KR900005656B1 (en) 1986-01-22 1987-01-21 Process for 6,7- dihydro -5,8- dimethyl-9-fluoro - 1-oxo- 1h, 5h - benzo (i,i) quinolizine-2-carboxylic acid

Country Status (6)

Country Link
EP (1) EP0245913B1 (ko)
JP (2) JPH0759579B2 (ko)
KR (1) KR900005656B1 (ko)
CA (1) CA1302413C (ko)
DE (1) DE3777685D1 (ko)
ES (1) ES2032438T3 (ko)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE793524A (fr) * 1971-12-30 1973-06-29 Riker Laboratories Inc Acides benzoquinolizine-carboxyliques et leurs derives
US4472405A (en) * 1982-11-12 1984-09-18 Riker Laboratories, Inc. Antimicrobial 6,7-dihydro-5,8-dimethyl-9 fluoro-1-oxo-1H, 5H-benzo (ij) quinolizine-2-carboxylic acid and derivatives
US4472407A (en) * 1983-03-17 1984-09-18 Riker Laboratories, Inc. Antimicrobial 8-alkoxy-6,7-dihydro-5-methyl-9-fluoro-1-oxo-1H,5H-benzo[ij]qu

Also Published As

Publication number Publication date
JPH0759579B2 (ja) 1995-06-28
JPH07300461A (ja) 1995-11-14
JP2593292B2 (ja) 1997-03-26
DE3777685D1 (de) 1992-04-30
JPS62201888A (ja) 1987-09-05
EP0245913A1 (en) 1987-11-19
CA1302413C (en) 1992-06-02
EP0245913B1 (en) 1992-03-25
ES2032438T3 (es) 1993-02-16
KR900005656B1 (en) 1990-08-03

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