KR860004026A - 알킬-1-시클로프로필-1,4-디히드로-4-옥소-3-퀴놀린 카르복실산의 제조방법 - Google Patents

알킬-1-시클로프로필-1,4-디히드로-4-옥소-3-퀴놀린 카르복실산의 제조방법 Download PDF

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KR860004026A
KR860004026A KR1019850008530A KR850008530A KR860004026A KR 860004026 A KR860004026 A KR 860004026A KR 1019850008530 A KR1019850008530 A KR 1019850008530A KR 850008530 A KR850008530 A KR 850008530A KR 860004026 A KR860004026 A KR 860004026A
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oxo
cyclopropyl
dihydro
quinolinecarboxylic acid
methyl
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KR870000784B1 (ko
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그로예 클라우스 (외 3)
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클라우스 데너 게르하르트 뷔네만
바이엘 악티엔 게젤샤프트
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    • 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
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
    • C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/116—Heterocyclic compounds
    • A23K20/132—Heterocyclic compounds containing only one nitrogen as hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents

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  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Food Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Animal Husbandry (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fodder In General (AREA)
  • Quinoline Compounds (AREA)

Abstract

내용 없음

Description

알킬-1-시클로프로필-1,4-디히드로-4-옥소-3-퀴놀린카르복실산의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 하기 일반식(I)으로 표시되는 알킬-1-시클로프로필-1,4-디히드로-4-옥소-3-퀴놀리카트복실산 및 약물학적으로 허용되는 그 염류.
    상기 식중, X1, X2및 X3는 수소 및(또는) 알킬기(탄소 원자수 1 내지 3개)이나, 단, X1, X2또는 X3중 어느 하나는 알킬기이며, X1, X2및(또는) X3는 또한 니트로기 또한 할로겐 원자이어도 좋다.
  2. 다음과 같은 화합물들, 즉 1-시클로프로필-6,8-디플루오로-7-메틸-1,4-디히드록-4-옥소-3-퀴놀린카르복실산,1-시클로프로필-6-플루르로-7-메틸-1,4-디히드로-4-옥소-3-퀴놀린카르복실산,1-시클로프로필-6-클로로-7-메틸-1,4-디히드로-4-옥소-3-퀴놀린카르복실산, 7-클로로-1-시클로프로필-8-메틸-1,4-디히드로-4-옥소-3-퀴놀린카르복실산-8-클로로-1-시클로프로필-6-플루오로-7-메틸-1,4-디히드로-4-옥소-3-퀴놀린카르복실산, 6-클로로-1-시클로프로필-8-플루오로-7-메틸-1,4-디히드로-4-옥소-3-퀴놀린카르복실산,7-클로로-1-시클로프로필-6-플루오로-8-메틸-1,4-디히드로-4-옥소-3-퀴놀린카르복실산,1-시클로프로필-6-플루오로-7-메틸-8-니트로-1,4-디히드로-4-옥소-3-퀴놀린카르복실산,1-시클로프로필-7-메틸-6,8-디니트로-1,4-디히드로-4-옥소-3-퀴놀린카르복실산,1-시클로프로토필-6-메틸-7-니트로-1,4-디히드로-4-옥소-3-퀴놀린카르복실산-6-클로로-1-시클로프로필-7-메틸-8-니트로-1,4-디히드로-4-옥소-3-퀴놀린카르복실산,7-클로로-1-시클로프로필-6-메틸-1,4-디히드로-4-옥소-3-퀴놀린카르복실산,1-시클로프로필-6,7-디메틸-1,4-디히드로-4-옥소-3-퀴놀린카르복실산,1-시클로프로필-6,7-디메틸-8-니트로-1,4-디히드로-4-옥소-3-퀴놀린카르복실산 및 1-시클로프로필-7-메틸-6-니트로-1,4-디히드로-4-옥소-3-퀴놀린카르복실산으로 되는 군중에서 선택된 알킬-1-시클로프로필-1,4-디히드로-4-옥소-3-퀴놀린카르복실산과 약물학적으로 허용되는 그의 알칼리금속염, 알칼리토금속 염 또는 수화물.
  3. 하기 일반식(1)의 치환벤조산을 일반식(2)의 대응하는 산 할로겐화물로 전환시키고, 디에틸말토네이트를 마그네슘 메틸레이트 존재하에 상기 치환 벤조일 할로겐화물(2)로 아실화시켜서 일반식(3)의 아로일말로네이트를 얻은 후, 이 아로일말로네이트(3)를 수용성 매질 중에서 촉매량의 황산 또는 p-톨투엔슬폰산을 사용해서 부분적으로 가수분해시키고, 탈카르복실화 시켜서 에틸 아로일아세테이트(4)로 전환시키고, 이 에틸 아로일아세테이트를 트리에틸 0-포트르이트/아세트산 무수물과 반응시켜 치환에틸 3-에톡시-아크릴레이트(5)를 얻은 다음, 이 반응 생성물(5)을 용매 중에서 시클로프로필아민을 사용하여 중간생성물(6)로 전환시키고, 이중간 생성물(6)을 60°내지 300℃의 온도에서 고리화시켜서 화합물(7)을 얻고, 최종적으로 화합물(7)을 가수 분해시켜서 하기 일반식(I)의 화합물은 얻은 후, 필요에 따라서 이 생성물을 약물학적으로 허용되는 그 염으로 전환시킴을 특징으로 하는 하기 일반식(I)으로 표시되는 알킬-1-시클로프로필-1,4-디히드로-4-옥소-3-퀴놀린카르복실산의 제조방법.
    [상기 식중, X1, X2및 X3는 수소 및(또는) 알킬기(탄소 원자수 1 내지 3개)이나, 단, X1, X2또는 X3기 중 어느 하나는 알킬기이며, X1, X2및(또는) X3는 또한 니트로기 또한 할로겐 원자이어도 좋고, X4는 할로겐 또는 니트로기이고, Hal는 할로겐 임].
  4. 제3항에 있어서, X4가 염소, 불소 또는 니트로기임을 특징으로 하는 방법.
  5. 제3 또는 4항에 있어서, 화합물(6)을 얻는 화합물(5)의 반응을 염화메틸렌, 에틸알코올, 클로로포름, 시클로헥산 또는 톨투엔 중에서 행함을 특징으로 하는 방법.
  6. 제3,4 또는 5항에 있어서, 화합물(7)을 얻는 화합물(6)의 반응을 디메틸술폭시드, N-메틸피롤리돈, 슬폴란, 헥사메틸인산 트리아미드 또는 디메틸포름아미드 중에서 행하고, 필요에 따라서, 산결합재로서 포태슘 tert. 부탄올레이트, 부틸-리튬, 리튬-페닐, 페닐-마그네슘 브로마이드, 소듐메틸레이트, 수소화나트륨 또는 탄산 칼륨 또는 탄산나트륨을 10몰% 과량으로 사용함을 특징으로 하는 방법.
  7. 하기 일반식(I)으로 표시되는 화합물 중 적어도 1개의 화합물과 약물학적으로 허용되는 그 염류를 함유시킴을 특징으로하는 의약품.
    [식중, X1, X2및 X3는 수소 및(또는) 알킬기(탄소 원자수 1 내지 3개)이나, 단, X1, X2또는 X3기중 어느 하나는 알킬기이며, X1, X2및(또는) X3는 또한 니트로기 또한 할로겐 원자이어도 좋음.]
  8. 하기 일반식(I)의 화합물 및 약물학적으로 허용되는 그 염류의 박테리아성 질병치료용도 또는 동물 영양 분야에 있어서 성장 촉진제의 제조 용도.
    [식중, X1, X2및 X3는 수소 및(또는) 알킬기(탄소 원자수 1 내지 3개)이나, 단, X1, X2또는 X3기중 어느 하나는 알킬기이며, X1, X2및(또는) X3는 또한 니트로기 또는 할로겐 원자이어도 좋음].
  9. 하기 일반식(I)이 화합물 및 약물학적으로 허용되는 그 염류의 의약품 또는 동물 영양 분야에 있어서 성장 촉진제의 제조용도.
    [식중, X1, X2및 X3는 수소 및(또는) 알킬기(탄소 원자수 1 내지 3개)이나, 단, X1, X2또는 X3기중 어느 하나는 알킬기이며, X1, X2및(또는) X3는 또한 니트로기 또는 할로겐 원자이어도 좋음].
  10. 다음과 같은 화합물들, 즉 1-시클로프로필-6,8-디플루오로-7-메틸-1,4-디히드로-4-옥소-3-퀴놀린카르복실산, 1-시클로프로필-6-플루오로-7-메틸-1,4-디히드로-4-옥소-3-퀴놀린카르복실산, 1-시클로프로필-6-클로로-7-메틸-1,4-디히드로-4-옥소-3-퀴놀린카르복실산, 7-클로로-1-시클로프로필-8-메틸-1,4-디히드로-4-옥소-3-퀴놀린카르복실산, 8-클로로-1시클로프로필-6-플루오로-7-메틸-1,4-디히드로-4-옥소-3-퀴놀린카르복실산, 6-클로로-1-시클로프로필-8-플루오로-7-메틸-1,4-디히드로-4-옥소-3-퀴놀린카르복실산,7-클로로-1-시클로프로필-6-플루오로-8-메틸-1,4-디히드로-4-옥소-3-퀴놀린카르복실산, 1-시클로프로필-6-플루오로-7-메틸-8-니트로-1,4-디히드로-4-옥소-3-퀴놀린카르복실산, 1-시클로프로필-7-메틸-6,8-디니트로-1,4-디히드로-4-옥소-3-퀴놀린카르복실산,1-시클로프로필-6-메틸-7-니트로-1,4-디히드로-4-옥소-3-퀴놀린카르복실산,6-클로로-1-시클로프로필-7-메틸-8-니트로-1,4-디히드로-4-옥소-3-퀴놀린카르복실산,7-클로로-1-시클로프로필-6-메틸-1,4-디히드로-4-옥소-3-퀴놀린카르복실산,1-시클로프로필-6,7-디메틸-1,4-디히드로-4-옥소-3-퀴놀린카르복실산,1-시클로프로필-6,7-디메틸-8-니트로-1,4-디히드로-4-옥소-3-퀴놀린카르복실산,1-시클로프로필-7-메틸-6-니트로-1,4-디히드로-4-옥소-3-퀴놀린카르복실산으로 되는 군중에서 선택된 화합물들 및 약제학적으로 허용되는 이들의 알킬리금속염, 알칼리토금속 염 또는 수화물의 의약품 또는 동물영양 분야에 있어서, 성장 촉진제의 제조용도.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019850008530A 1984-11-15 1985-11-14 알킬-1-시클로프로필-1,4-디히드로-4-옥소-3-퀴놀린 카르복실산의 제조 방법 KR870000784B1 (ko)

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DEP3441788.5 1984-11-15
DE19843441788 DE3441788A1 (de) 1984-11-15 1984-11-15 Alkyl-1-cyclopropyl-1,4-dihydro-4-oxo-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel

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KR860004026A true KR860004026A (ko) 1986-06-16
KR870000784B1 KR870000784B1 (ko) 1987-04-18

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US (1) US4762844A (ko)
EP (1) EP0181588A3 (ko)
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US5039682A (en) * 1988-06-21 1991-08-13 Pfizer Inc. 6-fluoro-1,4-dihydroquinol-4-one-3-carboxylic acid derivatives and intermediates therefor
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JP2915068B2 (ja) * 1990-05-07 1999-07-05 岩城製薬株式会社 ジヒドロフラノン誘導体の製造方法
DE4301246A1 (de) * 1993-01-19 1994-07-21 Bayer Ag Chinolon- und Naphthyridoncarbonsäurederivate
CA2327328C (en) * 1998-04-06 2007-11-13 Toyama Chemical Co., Ltd. Quinolonecarboxylic acid derivatives or salts thereof
DE10108750A1 (de) * 2001-02-23 2002-09-05 Bayer Ag Verbessertes Verfahren zur Herstellung von Fluorchinoloncarbonsäuren
KR100519158B1 (ko) * 2002-12-21 2005-10-06 주식회사유한양행 퀴놀론 카르복실레이트 유도체의 제조방법
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CA2848540A1 (en) 2011-09-15 2013-03-21 Arizona Board Of Regents, A Body Corporate Of The State Of Arizona Acting For And On Behalf Of Arizona State University Therapeutic compounds
US10328040B2 (en) 2014-01-17 2019-06-25 Arizona Board Of Regents On Behalf Of Arizona State University Therapeutic methods
US10231947B2 (en) 2017-01-23 2019-03-19 Arizona Board Of Regents On Behalf Of Arizona State University Isochroman compounds and methods of use thereof
US10238655B2 (en) 2017-01-23 2019-03-26 Arizona Board Of Regents On Behalf Of Arizona State University Dihydroindene and tetrahydronaphthalene compounds
US10238626B2 (en) 2017-01-23 2019-03-26 Arizona Board Of Regents On Behalf Of Arizona State University Therapeutic compounds
JP7282332B2 (ja) * 2017-10-25 2023-05-29 学校法人順天堂 リアノジン受容体阻害薬
CN113968787A (zh) * 2020-07-24 2022-01-25 广东东阳光药业有限公司 一种制备5-氟-4-甲基-2-硝基苯甲酸的方法

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ES8700851A1 (es) 1986-11-16
JPS61122272A (ja) 1986-06-10
ES548843A0 (es) 1986-11-16
EP0181588A3 (de) 1989-02-01
US4762844A (en) 1988-08-09
FI854466A (fi) 1986-05-16
CA1260478A (en) 1989-09-26
FI854466A0 (fi) 1985-11-13
HU194178B (en) 1988-01-28
AU572702B2 (en) 1988-05-12
KR870000784B1 (ko) 1987-04-18
DE3441788A1 (de) 1986-05-15
BR8505734A (pt) 1986-08-12
CS813285A2 (en) 1987-03-12
HUT40422A (en) 1986-12-28
AU4917785A (en) 1986-05-22
ZA858733B (en) 1986-07-30
PL256260A1 (en) 1986-12-30
EP0181588A2 (de) 1986-05-21
CS252835B2 (en) 1987-10-15
PL145639B1 (en) 1988-10-31

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