KR920702345A - Pla_2및 리폭시게나제의 억제제로서의 치환된 인돌-,인덴-,피라노인돌-및 테트라하이드로카바졸-알칸산 유도체 - Google Patents

Pla_2및 리폭시게나제의 억제제로서의 치환된 인돌-,인덴-,피라노인돌-및 테트라하이드로카바졸-알칸산 유도체

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KR920702345A
KR920702345A KR1019920700971A KR920700971A KR920702345A KR 920702345 A KR920702345 A KR 920702345A KR 1019920700971 A KR1019920700971 A KR 1019920700971A KR 920700971 A KR920700971 A KR 920700971A KR 920702345 A KR920702345 A KR 920702345A
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methyl
compound
acetic acid
quinolinylmethoxy
indole
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헨리 머서 존
프랭크 크레프트 3세 안토니
아르투로 페일리 아메데오
알렉산더 디머슨 크리스토퍼
샨티랄 샤 우레쉬
알버트 넬슨 제임스
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이건 이.버그
아메리칸 홈 프로덕츠 코포레이션
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    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/22—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an aralkyl radical attached to the ring nitrogen atom
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    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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Abstract

내용 없음

Description

PLA2및 리폭시게나제의 억제제로서의 치환된 인돌-,인덴-,피라노인돌-및 테트라하이드로카바졸-알칸산 유도체
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (47)

  1. 하기 일반식의 화합물 및 이의 약제학적으로 허용되는 염.
    A(CH2)n-O-B
    상기식에서, A는 C4-C8알킬, 페녹시에틸, 페녹시페닐 또는 일반식
    [여기서,
    X는 -N- 또는이고,
    Z는-S- 또는 -O-이며 R1은 수소, 저급 알킬, 페닐이거나 트리플루오로메틸로 치환된 페닐이고, R2는 수소 또는 저급알킬이거나, R1및 R2가 함께 벤젠환을 형성하고, R3는 수소 또는 저급알킬이다]을 갖는 그룹이며 n은 1 내지 2이고 B는 일반식
    [여기서
    R4는 -CO2R2,이며, m은 0내지 3이고, R5는,
    또는 페닐이거나, 할로, 저급 알킬티오, 저급 알킬설피닐 또는 저급 알킬설포닐로 치환된 페닐이며, R6은 A(CH2)no-또는 할로이고, 단 R6가 할로인 경우 , R5는
    이며, R7은 저급 알킬이고, Y는 -CH2-또는 -O-이며, R6은 저급알킬 또는 -(CH2)mCO2R3이고, R9는또는 -CH2R10이며, R10은 저급알킬 또는 페닐이거나, 카복시, 할로, 저급알킬티오 또는 저급알킬설피닐로 치환된 페닐이거나, 피리딜, 푸라닐 또는 퀴놀리닐이고, R11은 저급 알킬 또는 페닐이다]을 갖는 그룹이다.
  2. 제1항에 있어서, 3-[(4-클로로페닐)메틸렌]-[2-메틸렌]-(2-퀴놀리닐메톡시)]-3H-인덴-1-아세트산인 화합물.
  3. 제1항에 있어서, 2-메틸-3[[4-(메틸티오)페닐]메틸렌]]-6-(2-퀴놀리닐메톡시)-3H-인덴-1-아세트산인 화합물.
  4. 제1항에 있어서, 2-메틸-3-[[4-(메틸설피닐)페닐]-메틸렌]]-6-(2-퀴놀리닐메톡시)-3H-인덴-1-아세트산인 화합물.
  5. 제1항에 있어서, 5-플루오로-2-메틸-1-[[4-(2-퀴놀리닐메톡시)페닐]메틸렌]-1H-인덴-3-아세트산인 화합물.
  6. 제1항에 있어서, 2-메틸-3-[[4-(메틸티오)페닐]메틸렌]]-6-[(2-나프틸)메톡시]-3H-인덴-1-아세트산인 화합물.
  7. 제1항에 있어서, 3-[(4-클로로페닐)메틸렌]-[2-메틸-6-(2-퀴놀리닐메톡시)-3H-인덴-1-아세트산인 화합물.
  8. 제1항에 있어서, 3-[(4-클로로페닐)메틸렌]-[2-메틸-6-(2-퀴놀리닐메톡시)-3H-인덴-1-아세트산 메틸 에스테르인 화합물.
  9. 제1항에 있어서, 1,8-디에틸-1,3,4,9-테트라하이드로-6-(2-퀴놀리닐메톡시)피라노[3,4-b]인돌-1-아세트산인 화합물.
  10. 제1항에 있어서, 1-에틸-1,3,4,9-테트라하이드로-6-(2-퀴놀리닐메톡시)피라노[3,4-b]인돌-1-아세트산인 화합물.
  11. 제1항에 있어서, 1-메틸-1,3,4,9-테트라하이드로-6-(2-퀴놀리닐메톡시)피라노[3,4-b]인돌-1-아세트산인 화합
  12. 제1항에 있어서, 1-에틸-2,3,4,9-테트라하이드로-6-(2-퀴놀리닐메톡시)-1H-카바졸-1-아세트산인 화합물.
  13. 제1항에 있어서, 1,3,4,9-테트라하이드로-1-프로필-6-(2-퀴놀리닐메톡시)피라노[3,4-b]인돌-1-아세트산인 화합물.
  14. 제1항에 있어서, 1-에틸-1,3,4,9-테트라하이드로-6-(2-퀴놀리닐메톡시)피라노[3,4-b]인돌-1-아세트산 메틸 에스테르인 화합물.
  15. 제1항에 있어서, 1,3,4,9-테트라하이드로-1,1-디메틸-6-(2-퀴놀리닐메톡시)피라노[3,4-b]인돌인 화합물.
  16. 제1항에 있어서, 1,3,4,9-테트라하이드로-1,1-디에틸-6-(2-퀴놀리닐메톡시)피라노[3,4-b]인돌인 화합물.
  17. 제1항에 있어서, 1-[(4-클로로페닐)메틸]-2-메틸-5-(2-퀴놀리닐메톡시)-1H-인돌-3-아세트산인 화합물.
  18. 제1항에 있어서, 1-[(4-클로로페닐)메틸]-2-메틸-5-(2-퀴놀리닐메톡시)-1H-인돌-3-아세트산 메틸 에스테르인 화합물.
  19. 제1항에 있어서, 1-[(4-클로로벤조일)-2-메틸-5-(2-퀴놀리닐메톡시)-1H-인돌-3-아세트산인 화합물.
  20. 제1항에 있어서, 1-[(4-클로로벤조일)-2-메틸-5-(2-퀴놀리닐메톡시)-1H-인돌-3-아세트산 메틸 에스테르인 화합물.
  21. 제1항에 있어서, 2-메틸-5-(2-퀴놀리닐메톡시)-1,2-(퀴놀리닐메틸)-1H-인돌-3-아세트산인 화합물.
  22. 제1항에 있어서, 1-[(4-클로로페닐)메틸]-5-(헥실옥시)-2-메틸-1H-인돌-3-아세트산인 화합물.
  23. 제1항에 있어서, 2-메틸-5-(2-퀴놀리닐메톡시)-1-(2-(퀴놀리닐메틸)-1H-인돌-3-카복실산 에틸에스테르인 화합물.
  24. 제1항에 있어서, α-메틸-6-(2-퀴놀리닐메톡시)-9-(2-(퀴놀리닐메틸)-9H-카바졸-2-아세트산인 화합물.
  25. 제1항에 있어서, 1-[(4-클로로페닐)메틸]-2-메틸-N-(메틸)-N-(하이드록시)-5-(2-퀴놀리닐메톡시)-1H-인돌-3-아세트아미드인 화합물.
  26. 제1항에 있어서, 1-[(4-클로로페닐)메틸]-2메틸-N-(페닐설포닐)-5-(2-퀴놀리닐메톡시)-1H-인돌-3-아세트아미드인 화합물.
  27. 제1항에 있어서, 1-[(4-플루오로페닐)메틸]-2-메틸-5-(2-퀴놀리닐메톡시)-1H-인돌-3-아세트산인 화합물.
  28. 제1항에 있어서, 1[(4-클로로페닐)메틸]-2-메틸-5-(2-퀴놀리닐메톡시)-1H-인돌-3-아세트산인 화합물.
  29. 제1항에 있어서, 1-[(페닐)메틸-2-메틸]-5-(2-퀴놀리닐 메톡시)-1H-인돌-3-아세트산인 화합물.
  30. 제1항에 있어서, 1-[(4-클로로페닐)메틸]-2-메틸-5-(2-퀴놀리닐메톡시)-1H-인돌-3-아세트산인 화합물.
  31. 제1항에 있어서, 2-메틸-5-(2-퀴놀리닐메톡시)-1-[[4-(2-퀴놀리닐메톡시)페닐]메틸]-1H-인돌-3-아세트산인 화합물.
  32. 제1항에 있어서, 2-메틸-1-펜틸-5-(2-퀴놀리닐메톡시)-1H-인돌-3-아세트산인 화합물.
  33. 제1항에 있어서, 1-헥실-1-메틸-5-(2-퀴놀리닐메톡시)-1H-인돌-3-아세트산인 화합물.
  34. 제1항에 있어서, 1-헵틸-1-메틸-5-(2-퀴놀리닐메톡시)-1H-인돌-3-아세트산인 화합물.
  35. 제1항에 있어서, 1-메틸-1-메틸-5-(2-퀴놀리닐메톡시)-1H-인돌-3-아세트산인 화합물.
  36. 제1항에 있어서, 1-[(4-클로로페닐)메틸]-5-(2-퀴놀리닐메톡시)-11H-인돌-3-아세트산인 화합물.
  37. 제1항에 있어서, 1-[(4-클로로페닐)메틸]-2메틸-5-(2-나프탈레닐메톡시)-1H-인돌-3-아세트산인 화합물.
  38. 제1항에 있어서, 1-[(4-클로로페닐)메틸]-2-메틸-5-(2-페닐메톡시)-1H-인돌-3-아세트산인 화합물.
  39. 제1항에 있어서, 1-[(4-클로로페닐)메틸]-2-메틸-5-(피리디닐메톡시)-1H-인돌-3-아세트산인 화합물.
  40. 제1항에 있어서, 1-[(4-클로로페닐)메틸]-2-메틸-5-(2-벤조티아졸릴메톡시)-1H-인돌-3-아세트산인 화합물.
  41. 제1항에 있어서, 1-[(4-클로로페닐)메틸]-2-메틸-5-(2-페닐-4-티아졸릴)메톡시)-1H-인돌-3-아세트산인 화합물.
  42. 제1항에 있어서, 1-[(4-클로로페닐)메틸]-2-메틸-5-(2-(4-트리플루오로메틸페닐)-4-티아졸릴]-1H-인돌-3-아세트산인 화합물.
  43. 제1항에 있어서, 1-[(페닐)메틸]-2-메틸-5-[(2-페닐-4-티아졸릴)메톡시]-1H-인돌-3-아세트산인 화합물.
  44. 제1항에 있어서, 2-메틸-5-(2-페닐메톡시)-1-[[4-(2-퀴놀리닐메톡시)페닐]메틸렌]-1H-인덴-3-아세트산인 화합물.
  45. 제1항에 있어서, N-[[1-[(4-클로로페닐)메틸]-2-메틸-5-(2-페닐메톡시)-1H-인돌-3-일]-메틸]-N'-하이드록시우레아인 화합물.
  46. a)ⅰ)일반식(a)의 화합물을 일반식(b)의 화합물로 에테르화시킨 다음 트리에틸포스토노아세테이트와 반응시키고, 생성된 아세트산 에스테르 중간체를 가수분해시킨 다음 적합하게 치환된 벤즈알데하이드와 반응시켜서 목적하는 R5CH=잔기를 중간체에 도입하여 R6가 A(CH2)n0-인 일반식(Ⅰ)의 최종 생성물을 수득하거나; ⅱ)일반식 (c)의 중간체를 적합하게 치환된 벤즈알데하이드와 반응시켜 목적하는 R5CH=잔기를 상기 중간체에 도입한 다음 상기 중간체를 일반식(b)의 화합물러 에테르화시키고, 경우에 따라 이 중간체를 가수분해시켜서 R3가 수소이고 R6가 A(CH2)n0-인 일반식(Ⅰ)의 최종 생성물을 수득하거나; b)일반식(d)의 화합물을 일반식(e)의 화합물과 반응시키고, 경우에 따라, 이 최종 생성물 유리산을 에스테르화 시켜 R6가 할로이고, R5가
    A(CH2)n0
    인 c)ⅰ)일반식(f), (g)또는 (h)의 화합물을 일반식(b)의 화합물로 에테르화시키고, 경우에 따라, 중간체가 에스테르 작용기-CO2R3또는 -CO2R2를 갖는 경우, 이 중간체를 가수분해시켜 잔기 -CO2R2또는 -CO2R3의 R2또는 R3가 수소인 일반식(Ⅱ),(Ⅲ)또는 (Ⅳ)의 최종 생성물을 수득하거나; ⅱ)일반식(ⅰ)의 중간체 화합물을 일반식 R9hal(여기서, R9는 상기 정의한바와 같고 hal은 할로원자이다)의 화합물과 반응시켜서 일반식(Ⅳ)의 최종 생성물을 수득하거나, d)-CO2R2또는 -CO2R3잔기가 에스테르 작용기인 일반식(Ⅰ),(Ⅱ),(Ⅲ)또는 (Ⅳ)의 화합물을 가수분해시켜서 상기 잔기에서 R2또는 R3가 수소인 화합물 또는 이의 약물학적으로 허용되는 염을 수득하거나; e)일반식(Ⅰ),(Ⅱ),(Ⅲ)또는 (Ⅳ)의 화합물을 약물학적으로 허용되는 염으로 전환시키는 방법을 포함함을 특징으로 하여, 제1항에 따른 화합물을 제조하는 방법.
    상기식에서, R2내지R9,A,Y,m및 n은 제1항에서 정의된 바와 동일하며, 단 일반식 (c)에서 -COOR3잔기의 R3는 저급알킬이고, X는 이탈 그룹이며, hal은 할로 원자이다.
  47. 제46항에있어서, 실시예, 1E,1F,1G,2,3,4,5B,5C,6C,6E,6F,7,8E,9D,10D,11C,12C,13,14C,15C,16A,16C,16D,17,18,19,20,21F 및 22내지 42까지 중 어느 하나에서 실질적으로 또는 상기한 바와 같이 기술되고 예시된 제조방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019920700971A 1989-10-27 1990-10-27 Pla_2및 리폭시게나제의 억제제로서의 치환된 인돌-,인덴-,피라노인돌-및 테트라하이드로카바졸-알칸산 유도체 KR920702345A (ko)

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