KR890003735A - 항균제로서의 8-트리플루오로 메틸 퀴놀론 - Google Patents

항균제로서의 8-트리플루오로 메틸 퀴놀론 Download PDF

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KR890003735A
KR890003735A KR1019880009582A KR880009582A KR890003735A KR 890003735 A KR890003735 A KR 890003735A KR 1019880009582 A KR1019880009582 A KR 1019880009582A KR 880009582 A KR880009582 A KR 880009582A KR 890003735 A KR890003735 A KR 890003735A
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compound
methyl
trifluoro
oxo
dihydro
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제임스 브리지스 알렉산더
미카엘 도마갈타 존
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크리스틴 에이.트라우트 웨인
워너-램버트 컴퍼니
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • 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
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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

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  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

내용 없음

Description

항균제로서의 8-트리플루오로 메틸 퀴놀론
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (31)

  1. 다음 구조식 화합물이나 이들의 제약학적으로 허용가능한 산부가염 또는 염기 염.
    식중, R1은 수소, C1-6알킬 또는 양이온; R2는 C1-4알킬, C1-4비닐, 할로알킬 또는 하이드록시알킬 또는 C3-6시클로알킬; Y는 수소, 불소 또는 아미노; Z는 다음구조식의 것들이며
    n이 1,2,3 또는 4; n′가 1,2,3 또는 4; n+n′의 합이 2,3,4 또는 5; n″이 0,1 또는 2; n′″가 0,1 또는 2; nⅣ가 1,2 또는 3; nⅤ가 0 또는 1; R3가 수소, C1-4알킬 또는 C3-6시클로알킬; R4가 수소, C1-4알킬, C2-4하이드록시알킬, 트리플루오로에틸, 또는 R4′가 C1-4알킬 또는 C1-4알콕시인 R4′CO; R5및 R6는 각각 독립적으로 수소 또는 C1-3알킬; R7은 수소, C1-3알킬, C2-3하이드록시 알킬, 벤질 또는 p-아미노벤질; R8및 R9은 각각 독립적으로 수소, C1-3알카노일, C1-3알킬, 이소프로필 또는 시클로프로필; R10및 R11은 각각 독립적으로 수소, 메틸, 에틸, 또는 벤질; R12,R13, 및 R14은 각각 독립적으로 수소 또는 메틸; R15은 메틸, 에틸, 또는 이소프로필; R16은 R18및 R19가 수소, C1-3알킬, C1-3알카노일인 CH2OR18, CH2NR18R19또는 NR18R19: R17은 부재, 수소 또는 C1-3알킬: 점선을 단일 또는 이중결합; R20및 R21은 R22와 R23가 각각 독립적으로 수소, C1-3알킬, C1-3아실인 각각 독립적으로 수소, 할로겐 NR22R23, OR22,SR22, C1-3알킬.
  2. 제1항에 있어서, R2가 에틸, 비닐, 2-플루오로에틸, 디플루오로에틸, 또는 시클로프로필인 화합물.
  3. 제1항에 있어서, Z가 다음 구조식
    또는 다음 구조식인 화합물.
    식 중, R3는 수소, 메틸, 에틸, n-프로필, 또는 2-프로필, R5및 R6는 수소, 메틸, 또는 에틸 및 n″는 0 또는 1.
  4. 제1항에 있어서, R이 수소 또는 이것의 제약학적으로 허용가능한 염기 염인 화합물.
  5. 제1항에 있어서, 7-(3-아미노메틸)피롤리딘-1-일)-1-에틸-6-플루오로-8-(트리플루오로 메틸)-1,4-디하이드로-4-옥소퀴놀린-3-카복실산인 화합물.
  6. 제1항에 있어서, 7-[3-(1-아미노메틸)-1-피롤리딘일]-1-시클로프로필-6-플루오로-1,4-디하이드로-4-옥소-8-(트리플루오로메틸)-3-퀴놀린카복실산인 화합물.
  7. 제1항에 있어서, 1-시클롤프로필-7-[3-[1-(1-에틸아미노 에틸]-1-피롤리딘일]-6-플루오로-1,4-디하이드로-4-옥소-8-(트리플루오로 메틸)-3-퀴놀린카복실산인 화합물.
  8. 제1항에 있어서, 1-시클로프로필-6-플루오로-1,4-디하이드로-7-[1-메틸-1-(메틸아미노)에틸]-1-피롤리딘일]-4-옥소-8-(트리플루오로메틸)-3-퀴놀린카복실산인 화합물.
  9. 제1항에 있어서, 7-[3-(1-아미노메틸)-1피롤리딘일]-1-시클로프로필-6-플루오로-1,4-디하이드로-4-옥소-8-(트리플루오로메틸)-3-퀴놀린카복실산인 화합물.
  10. 제1항에있어서, 1-에틸-6-플루오로-1,4-디하이드로-7-[3-[(메틸아미노)메틸-1-피롤리딘일]-4-옥소-8-(트리플루오로 에틸)-3-퀴놀린카복실산인 화합물.
  11. 제1항에 있어서, 1-시클로프로필-6-플루오로-1,4 디하이드로-7-[3-[(메틸아미노)메틸]-1-피롤리딘일]-4-옥소-8-(트리플루오로 메틸)-3-퀴놀린카복실산인 화합물.
  12. 제1항에 있어서, 1-에틸-7-[3-(에틸아미노)메틸]-1-피롤리딘일]-6-플
    루오로-1,4-디하이드로-4-옥소-8-(트리플루오로 메틸)-3-퀴놀린카복실산인 화합물.
  13. 제1항에 있어서, 1-시클로프로필-7-[3-(에틸아미노)메틸]-1-피롤리딘일]-6-플루오로-1,4-디하이드로-4-옥소-8-(트리플루오로 메틸)-3-퀴놀린카복실산인 화합물.
  14. 제1항에 있어서, 1-에틸-6-플루오로-1,4-디하이드로-4-옥소-7-(1ㅡ피페라진일)-8-(트리플루오로 메틸)-3-퀴놀린카복실산인 화합물.
  15. 제1항에 있어서, 1-시클로프로필-6-플루오로-1,4-디하이드로-4-옥소--(1-피페라진일)-8-트리플루오로메틸)-3-퀴놀린카복실산인 화합물.
  16. 제1항에 있어서, 1-에틸-6-플루오로-1,4-디하이드로-7-(4-메틸-1-피페라진일)-4-옥소-8-(트리플루오로 메틸)-3-퀴놀린카복실산인 화합물.
  17. 제1항에 있어서, 1-시클로프로필-6-플루오로-1,4-디하이드로-7-(4-메틸-1-피페라진일)-4-옥소-8-(트리플루오로 메틸 )-3-퀴놀린카복실산인 화합물.
  18. 제1항에 있어서, 1-시클로프로필-6-플루오로-1,4-디하이드로-7-(3-메틸-1-피페라진일)-4-옥소-8-(트리플루오로 메틸 )-3-퀴놀린카복실산인 화합물.
  19. 제1항에 있어서, 7-(3-아미노-1-피롤리딘일)-1-에틸-6-플루오르-1,4-디하이드로-4-옥소-8-(트리플루오로 메틸)-3-퀴놀린카복실산인 화합물.
  20. 제1항에 있어서, 7-(3-아미노-1-피롤리딘일)--시클로프로필-6-플루오로 -1,4-디하이드로-4-옥소-8(트리플루오로 메틸)-3-퀴놀린카복실산인 화합물.
  21. 제1항에 있어서, 7-[3-(1-아미노-1-메틸에틸)-1-피롤리딘일]-1-시클로프로필-6-플루오로-1,4-디하이드로-4-옥소-8-(트리플루오로 메틸)-3- 퀴놀린카복실산인 화합물.
  22. (a) 1-브로보- 2,4,5-트리플루오로 벤젠을 카복실화하여 3-브로모-2,5,6-트리플루오로 벤조산을 형성하고, (b) 상기 화합물의 카복실산 그룹을 불화하여 1-브로모-2,4,5-트리플루오로-3-(트리플루오로 메틸)벤젠을 형성시키며, (c) 상기 화합물의 브롬을 카복실화하여 2,4,5- 트리플루오로-3-(트리플루오로 메틸)벤조산을 형성시키며, (d) 상기 벤조산 화합물을 염소화제, 알킬 하이드로젠 말로네이트, 및 n-부틸 리튬과 반응시켜 알킬 2,4,5-트리플루오로-β-옥소-3-(트리플루오로 메틸)벤젠 트로파노에이트 생성물을 형성시키고, (e) 상기 생성물을 알킬 오르토포트메이트 및 무수 아세트산, 다음에 1차 알킬 아민과 반응시켜 알킬α-(N-알킬아미노메틸렌)-2,4,5-트리플루오로-β-옥소-3-(트리플루오로 메틸)벤젠 프로파노에이트를 형성시키며 (f) 상기 화합물을 용매내의 염기와 반응시켜 환화하여 알킬 1-알킬-6,7-디플루오로-1,4-디하이드로-4-옥소-8-(트리플루오로 메틸)-3-퀴놀린카복실레이트를 형성시키고, (g) 상기 카복실레이트를 탈에스테르화하여 상응하는 카복실산을 형성시키며, (h) 상기한 카복실산을 2차 아민과 반응시켜 구조식(Ⅰ)화합물을 형성하고, 원한다면 이것의 제약학적으로 허용가능한 산부가염 또는 염기염으로 전환시키는 것으로 구성되는, 제1항 화합물의 제조방법.
  23. 제22항에 있어서, 단계(h)의 2차 아민이 다음 것들인 방법.
  24. 3-브로모-2,5,6-트리플루오로 벤조산인 화합물.
  25. 1-브로모-2,4,5-트리플루오로-3-(트리플루오로 메틸)벤젠인 화합물.
  26. 2,4,5-트리플루오로-3-(트리플루오로 메틸)벤조산인 화합물.
  27. 에틸 2,4,5-트리플루오로-β-옥소-3-(트리플루오로 메틸)벤젠프로파노에이트인 화합물.
  28. 에틸 1-시클로프로필-6,7-디플루오로-1,4-디하이드로-4-옥소-8-(트리플루오로 메틸)-3-퀴놀린카복실레이트인 화합물.
  29. 1-시클로프로필-6,7-디플루오로-1,4-디하이드로-4-옥소-8-(트리플루오로 메틸)-3-퀴놀린카복실산인 화합물.
  30. 항균적으로 효과적인 양의 제1항 화합물과 제약학적으로 허용가능한 담체로 구성된 제약학적 조성물.
  31. 제30항의 제약학적 조성물을 박테리아에 감염된 포유 동물에게 단위 투약 형태로 투여하는 것으로 구성된, 박테리아 감염의 치료방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019880009582A 1987-08-07 1988-07-29 항균제로서의 8-트리플루오로 메틸 퀴놀론 KR890003735A (ko)

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US083532 1987-08-07
US07/083,532 US4780468A (en) 1987-08-07 1987-08-07 8-trifluoromethyl quinolones as antibacterial agents

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KR890003735A true KR890003735A (ko) 1989-04-17

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EP (1) EP0302525A3 (ko)
JP (1) JPS6466180A (ko)
KR (1) KR890003735A (ko)
AU (2) AU616422B2 (ko)
DK (1) DK439688A (ko)
FI (1) FI883628A (ko)
NO (1) NO883475L (ko)
NZ (1) NZ225626A (ko)
PH (1) PH24784A (ko)
PT (1) PT88203A (ko)
ZA (1) ZA885546B (ko)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20020072602A (ko) * 2001-03-12 2002-09-18 (주)인산 기능미의 제조방법
KR100448505B1 (ko) * 2001-11-28 2004-09-13 삼서농업협동조합 발아현미 제조방법
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KR100904977B1 (ko) * 2001-10-03 2009-06-26 가부시끼가이샤 사따께 발아배아미의 제조방법 및 장치
KR100448505B1 (ko) * 2001-11-28 2004-09-13 삼서농업협동조합 발아현미 제조방법

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DK439688A (da) 1989-02-08
NO883475D0 (no) 1988-08-04
PH24784A (en) 1990-10-30
EP0302525A2 (en) 1989-02-08
NZ225626A (en) 1991-03-26
US4780468A (en) 1988-10-25
FI883628A0 (fi) 1988-08-03
PT88203A (pt) 1989-06-30
NO883475L (no) 1989-02-08
AU2006088A (en) 1989-02-09
ZA885546B (en) 1990-03-28
AU8374391A (en) 1991-11-14
JPS6466180A (en) 1989-03-13
AU616422B2 (en) 1991-10-31
FI883628A (fi) 1989-02-08
DK439688D0 (da) 1988-08-05

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