KR890003751A - 화합물들 - Google Patents

화합물들 Download PDF

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Publication number
KR890003751A
KR890003751A KR1019880010261A KR880010261A KR890003751A KR 890003751 A KR890003751 A KR 890003751A KR 1019880010261 A KR1019880010261 A KR 1019880010261A KR 880010261 A KR880010261 A KR 880010261A KR 890003751 A KR890003751 A KR 890003751A
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South Korea
Prior art keywords
dihydro
oxo
methyl
thiadiazin
compound
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KR1019880010261A
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English (en)
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마르뗑 미쉘
나들레 기
짐메르망 리샤아르
Original Assignee
원본미기재
라보라뚜와르 소비오 소시에테 아노님
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Priority claimed from GB878718957A external-priority patent/GB8718957D0/en
Priority claimed from GB888811276A external-priority patent/GB8811276D0/en
Application filed by 원본미기재, 라보라뚜와르 소비오 소시에테 아노님 filed Critical 원본미기재
Publication of KR890003751A publication Critical patent/KR890003751A/ko

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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
    • C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/08—Bronchodilators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/32—Oxygen atoms
    • C07D209/34—Oxygen atoms in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/96—Spiro-condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/10—Spiro-condensed systems

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
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  • Veterinary Medicine (AREA)
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  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Pulmonology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

내용 없음

Description

화합물들
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (12)

  1. 하기 일반식(Ⅰ)의 화합물이나 약제학적으로 허용되는 그의 염:
    상기식에서 R1은 수소, 저급알킬 또는 CH2OR6; R2는 수소 또는 저급알킬; R3은 수소, 또는 저급알킬; W와 Z는 각각 상이한 것으로 -CR4R5- 또는 -(CRxRy)n- (여기에서 R4는 수소, C1-3알킬, C1-3알킬티오 또는 C1-3알콕시; R5은 C1-3알킬, C1-3알킬티오 또는 C1-3알콕시; 또는 R4와 R5은 함께 결합하여 3-6원 카르보시클릭 고리, 또는 1또는 2개의 고리산소, 질소, 또는 황원자를 함유하는 헤테로시클릭고리를 형성하거나 R4와 R5이 함께 결합하여 옥소 또는 메틸렌기를 형성하고; Rx와 Ry는 각각 수소 또는 C1-3알킬이고; n은 0또는 1); R6은 수소, 저급알킬, 저급 알킬가르보닐, 아릴카르보닐, 아르알킬 카르보닐, 헤테로아릴카르보닐, 임의치환 아미노카르보닐, 저급 알콕시 카르보닐 및 아릴옥시카르보닐; R7은 수소 또는 저급 알킬; X는 산소 또는 황; 및 A는 황, 산소 또는 -NH-.
  2. 제1항에 있어서, n이 0인 화합물.
  3. 제1항 또는 제2항에 있어서, A가 황인 화합물.
  4. 제1항 내지 제3항중 어느 하나에 있어서, X가 산소인 화합물.
  5. 제1항 내지 제4항중 어느 하나에 있어서, R4가 메틸이고 R5이 메틸이거나 티오메틸이거나 R4과 R5이 함께 시클로프로필, 시클로펜틸, 시클로헥실, 에틸렌디티오, 프로필렌디티오 또는 프로필렌티오기를 형성하는 화합물.
  6. 1,3-디히드로-5-(3,6-디히드로-2-옥소-2H-1,3,4-티아디아진-5일)-3-메틸-3-메틸티오-2H-인돌-2-온; 1,3-디히드로-5-(3,6-디히드로-2-옥소-2H-1,3,4-티아디아진-5-일)-3,3-디메틸-2H-인돌-2-온; 1,3-디히드로-5-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진-5-일)-3,3-디메틸-2H-2-온; 1,3-디히드로-5-(3,6-디히드로-2-옥소-2H-1,3,4-티아디아진-5-일)-3-메틸-2H-인돌-2-온; 1,3-디히드로-5-(3,6-디히드로-2-옥소-2H-1,3,4-티아디아진-5-일)-3-메틸-2H-인돌-2-온; 1,3-디히드로-5-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진-5-일)-스피로[시클로펜탄-1,3′-[3H]-인돌]-2′(1′H)온; 1-아세틸-1,3-디히드로-5-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진-5-일)-3,3-디메틸-2H-인돌-2-온; 1-아세틸-1,3-디히드로-5-(3,6-디히드로-2-옥소-2H-1,3,4-ㅣ티아디아진-5-일)-3-메틸-2H-인돌-2-온1-아세틸-1,3-디히드로-5-(3,6-디히드로-2-옥소-2H-1,3,4-티아디아진5-일)-3-메틸-3-메틸티오-2H-인돌-2-온 1,3-디히드로-5-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진-5-일)-3-메틸티오-2H-인돌-2-온 1,3-디히드로-5-(3,6-디히드로-2-옥소-2H-1,3,4-티아디아진-5-일)-3-메틸티오-2H-인돌-2-온5-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진-5-일)1H-인돌-2,3-디온 5′(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진-5-일)-스피로[1,3-디티올란-2,3′-[3H]인돌]-2(1′H)-온 5′-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진-5-일)스피로[1,3-디티안-2,3′-[3H]인돌]-2′(1′H )-온 1,3-디히드로-5-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진-5-일)-3,3-디(메틸티오)-2H-인돌-2-온 5-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진-5-일)-스피로[시클로프로판-1,3′-[3H]인돌]-2′-(1′H)-온 5′-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4티아디아진-5-일)-스피로[시클로헥산-1,3′-[3H]인돌]-2′-(1′H)-온 1,3-디히드로-5-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진-5-일)-1,3,4-트리메틸-2H-인돌-2-온 5-(3,6-디히드로-6-디메틸-2-옥소-2H-1,3,4-티아디아진-5-일)-1′메틸-스피로[시클로펜탄-1,3′-[3H인돌]-2′(1′H)-온 5′-(3,6-디히드로-2-옥소-2H-1,3,4-티아디아진-5-일)스피로[티올란-2,3′-[3H]-인돌]-2′-(1′H)온 5′-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진-5-일)스피로[티올란-2,3′-[3H]-인돌]-2′(1′H)-온 1-벤조일-1,3-디히드로-5-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진-5-일)-3,3-디메틸-2H-인돌-2-온 1,3-디히드로-5-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진-5-일)-3,3-디메틸-1-[(4-피리딜)카르보닐-2H-인돌]-2-온 1,3-디히드로-5-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진-5-일)-3,3-디메틸-1-[(3-피리딜 카르보닐]-2H-인돌-2-온 1,3-디히드로-5-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진-5-일)-3,3-디메틸-1-(4-니트로벤조일)-2H-인돌-2-온 1,3-디히드로-5-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진-5-일)-3,3-디메틸-1-(페닐메틸카르보닐)-2H-인돌-2-온 5′-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진-5-일)-1′[(4-피리딜)카르보닐]-스피로[시클로펜탄-1,3′-[3H-인돌]-2′-(1′H)-온 1-[2,3-디히드로-5-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진-5-일)-3,3-디메틸-2-옥소-1H-인돌-1-일]2,4-디페닐-1,3-부틴디온 1,3-디히드로-5-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진-5-일)-3,3,4-트리메틸-2H-인돌-2-온 1,3-디히드로-5-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진-5-일)-3,3,6-트리메틸-2H-인돌-2-온 1,3-디히드로-5-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진-5-일)-3,3,7-트리메틸-2H-인돌-2-온 1,3-디히드로-5-(3,6-디히드로-6,6-디메틸-2-옥소-2H-1,3,4-티아디아진-5-일)-3,3-디메틸-2H-인돌-2-온 1,3-디히드로-5-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진-5-일)3-히드록시-3-메틸-2H-인돌-2-온 에틸 2,3-디히드로-5-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진-5-일)3,3-디메틸-2-옥소-1H-인돌-1-카르복실레이트 1,3-디히드로-5-(1,2,3,6-테트라히드로-6-메틸-2-옥소-1,3,4-트리아진-5-일)-3,3-디메틸-2-H-인돌-2-온 1,3-디히드로-5-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-옥사디아진-5-일)-3,3-디메틸-2H-인돌-2-온 1,3-디히드로-5-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진-5-일)-1-(3,4-디메톡시벤조일)-3,3-디메틸-2H-인돌-2-온 페닐 2,3-디히드로-5-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진-5-일)-3,3-디메틸-2-옥소-1H-인돌-1-카르볼실레이트 3,4-디히드로-6-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진-5-일)-4,4-디메틸-2(1H)-퀴놀리논 3,4-디히드로-6-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진-5-일)-1′[(4-니트포페닐)카르보닐]-스피로[시클로펜탄-1,4′-[3H]인돌]-2′(1′H)-온 1,3-디히드로-5-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진-5-일)-3,3-디메틸-1-[(4-아미노페닐)카르보닐-2H-인돌-2-온 2,3-디히드로-5-5(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진-5-일)-3,3-디메틸-2-옥소-1H-인돌-1-카르복시아미드 에틸 1,2,3,4-테트라히드로-6-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진-5-일)-4,4-디메틸-2-옥소-1-퀴놀린 카르복실레이트5′-(3,6-디히드로-6-메틸-2-옥소-2H-1,3,4-티아디아진 5-일)스피로[이미다졸리딘-4,3′-[3H]인돌]-2,2′(1′H),5-트리온.
  7. (a)하기 일반식(Ⅱ)의 화합물을 하기 일반식(Ⅲ)의 화합물과 반응시킨 이후에, 임의적으로 X가 산소인 화합물을 X가 황인 화합물로 전환시키거나; (b)하기 일반식(Ⅳ)의 화합물을 환화시키거나; (c)하기 일반식(Ⅴ)의 화합물을 하기 일반식(Ⅵ)의 화합물로 처리하고; 단계(a), (b) 또는 (c) 이후에 임의적으로 일반식(Ⅰ)의 화합물을 약제학적으로 허용되는 염이나 일반식(Ⅰ)의 다른 화합물로 전환시키는 것으로 구성되는 하기 일반식(Ⅰ)의 화합물의 제조방법.
    상기식에서 R1은 수소, 저급알킬 또는 CH2CR6;R2는 수소 또는 저급알킬; R3은 수소 또는 저급알킬; W와 Z는 각각 상이한 것으로 -CR4R5- 또는 -(CRxRy)n-(여기에서 R4는 수소, C1-3알킬, C1-3알킬티오 또는 C1-3알콕시; R5은 C1-3알킬, C1-3알킬티오 또는 C1-3알콕시; 또는 R4와 R5은 함께 결합하여 3-6원 카르보시클릭고리, 또는 1 또는 2개의 고리 산소, 질소 또는 황원자를 함유하는 헤테로시클릭 고리를 형성하거나 R4와 R5이 함께 결합하여 옥소 또는 메틸렌기를 형성하고; Rx와 Ry는 각각 수소 또는 C1-3알킬이고; n은 0 또는 1); R6은 수소, 저급알킬, 저급 알킬카르보닐, 아릴카르보닐, 아르알킬카르보닐, 헤테로아릴카르보닐, 임의 치환 아미노카르보닐, 저급 알콕시 카르보닐, 및 아릴옥시카르보닐; R7은 수소 또는 저급 알킬; X는 산소 또는 황; 및 A는 황, 산소 또는 -NH-;
    상기식에서 R1, R2, R6, R7, W 및 Z는 일반식(Ⅰ)에서 정의한 바와 같고 Y는 이탈기;
    상기식에서 R3과 X는 일반식(Ⅰ)에서 정의한 바와 같고 Ra는 알킬기;
    상기식에서 R1, R2,R6,R7,X,W 및 Z는 일반식(Ⅰ)에서 정의한 바와 같고 R8은 알킬기;
    상기식에서 R1, R2, R6, R7, X, W 및 Z는 일반식(Ⅰ)에서 정의한 바와 같고 R8은 일반식(Ⅳ)에서 정의한 바와 같다;
    H2N-NH-R3(Ⅵ)
    상기식에서 R3는 일반식(Ⅰ)에서 정의한 바와 같다.
  8. 제7항에서 정의한 바와 같은 일반식(Ⅱ),(Ⅳ) 또는 (Ⅴ)의 화합물.
  9. 제1항에서 정의된 일반식(Ⅰ)의 화합물이거나 약제학적으로 허용 가능한 그의 염 및 약제학적으로 허용 가능한 담체를 포함하는 약제학적인 조성물.
  10. 활성 치로 물질로서 사용되기 위한 일반식(Ⅰ)의 화합물 또는 약제학적으로 허용가능한 그의 염.
  11. 심장질환이나 천식의 치료에 사용되기 위한 제1항에서 정의된 바와 같은 일반식(Ⅰ)의 화합물이나 그의 약제학적으로 허용되는 염.
  12. 심장 질환이나 천식의 치료를 위한 약제의 제조에 제1항에서 정의된 바와 같은 일반식(Ⅰ)의 화합물이나 약제학적으로 허용 가능한 그의 염을 사용.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019880010261A 1987-08-11 1988-08-11 화합물들 KR890003751A (ko)

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CO5200852A1 (es) 1999-09-14 2002-09-27 Lilly Co Eli Moduladores rxr con mejorado perfil farmacologico ceptores x de los retinoides
ATE521599T1 (de) * 2001-12-21 2011-09-15 X Ceptor Therapeutics Inc Heterocyclische modulatoren von nukleären rezeptoren
JP4709759B2 (ja) * 2003-08-22 2011-06-22 リガンド・ファーマシューティカルズ・インコーポレイテッド アンドロゲン受容体モジュレーター化合物としての６−シクロアミノ−２−キノリノン誘導体
CN107235992B (zh) * 2017-07-06 2019-08-20 中国人民解放军第四军医大学 吲哚酮螺四氢噻吩类化合物及其盐、制备方法和应用
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PT88224A (pt) 1989-06-30
US4933336A (en) 1990-06-12
EP0303418A2 (en) 1989-02-15
JPH01110681A (ja) 1989-04-27
DK445288D0 (da) 1988-08-09
DK445288A (da) 1989-02-12
EP0303418A3 (en) 1990-11-07
PT88224B (pt) 1995-03-01
AU2056688A (en) 1989-02-16

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