KR920701134A - 치료학적으로 유용한 2-아미노테트랄린 유도체 - Google Patents

치료학적으로 유용한 2-아미노테트랄린 유도체

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Publication number
KR920701134A
KR920701134A KR1019910701735A KR910701735A KR920701134A KR 920701134 A KR920701134 A KR 920701134A KR 1019910701735 A KR1019910701735 A KR 1019910701735A KR 910701735 A KR910701735 A KR 910701735A KR 920701134 A KR920701134 A KR 920701134A
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South Korea
Prior art keywords
tetrahydro
hydrochloride
methoxy
naphthalenamine
propenyl
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KR1019910701735A
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English (en)
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KR100195656B1 (ko
Inventor
린 치우-홍
알. 하드스마 수잔느
에프. 피어시 몬트포드
글렌 로메로 아더
에이치. 달링톤 윌리암
Original Assignee
로버트 에이. 아미테이지
디 업존 캄파니
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Publication of KR920701134A publication Critical patent/KR920701134A/ko
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Publication of KR100195656B1 publication Critical patent/KR100195656B1/ko

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    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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Abstract

내용 없음

Description

치료화적으로 유용한 2-아미노테트랄린 유도체
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (29)

  1. 하기 일반식(I)의 화합물:
    상기식에서, R은 수소 또는 할로겐이고 R1은 (a)-수소, (b)-OR6, (c)-SR6, (d) - CONR7R8, (e)-CN ,(f)-het, (g) -C(O)het, (h), -CF3, (i) - SO2NR7R8, (j) -5-옥사졸릴, (k)-CSNR7R8이며, R2는 (a)-수소 (b),-(C1-C8)알킬, (c) -(C3-C5)알케닐, (d) - (C3-C8)알키닐, (e) -(CH2)m-(C3-C8)사이클로알킬, (f) -(CH2)m-(C3-C8)사이클로알케닐,(g)-(CH2)m-아릴, (h) 트리메틸실리메틸이고,R3는 (a)-수소, (b)-(C1-C8)알킬,(c)-(C3-C5)알케닐,(d)-C3-C8알키닐,(e)-(CH2)m-(C3-C8)사이클로알킬, (f)-(CH2)m-(C3-C8)사이클로알케닐,(g)-(CH2)m-아릴,(h)트리메틸실리메틸이고, (i)-(CH2)m(R10에 의해 N-치환되고 R9에 의해 고리-치환딘 인돌),(j)-(CH2)m-6-페닐-4H-5-트리아졸로(4,3-a)(1,4)벤조디아조피닐, 6-페닐-및 Y에 의해 치환된 아릴 고리, (k)〔2-(2,3-디하이드로-1,1-디옥소-3-옥소-벤즈이소 티아졸릴)-(CH2)n,(1)-(할로-페닐)-2-이미다졸리돈-3-일-(CH2)n,(m)2,4-디하이드로 -1-옥소-1H-(2,3,4)트리아졸로(3,4,-c)(1,4) 벤즈옥사지닐-(CH2)n,(n)R2및 R3는 질소원자와 함께 -이며, R4및 R5는 독립적으로 (a)-수소, (b)-(C1-C8)알킬 (c) -(C2-C8)알케닐, (d)-(C2-C8)알키닐, (e)-(CH2)m-(C3-C8)사이클로알킬, (f)-(CH2)m-(C3-C8)사이클로알케닐,(g)-(CH2)m-아릴, (h)-(CH2)m-CO2R6, (i) -(CH2)m-OR6이고, R6, R7, 및 R8은 독립적으로 (a)-수소, (b) -(C1-C4)알킬, (c) -(C1-C4)알케닐, (d) -(C3-C8)사이클로알킬이며, X는 (a)-(CR6R6)n-, (b)-(CR6R6)n-알케닐(CR6R6)n-, (c)-(CR6R6)n-O-(CR6R6)q-, (d)-(CR6R6)n-S-(CR6R6)q-,(e)-(CR6R6)n-NR6-(CR6R6)q-이고, R9는 (a)-수소ㅡ (b)-OR6, (c)-SR6이며, R10은 (a) -수소, (b) - (C1-C4)알킬, (e) -C(O)알킬, (f) -C(O)알릴이고, Y는 수소 또는 할로겐이며, m은 0 내지 4이고, n은 1내지 3이며, p는 0내지 1이고, q는 1내지 3이며, 단, R1이 하이드록시 또는 메톡시이고, R4가 수소일때 , R2및 R3가 모두 수소, 동일한 알킬 또는 사이클로 프로필메틸일 수는 없으며, R2및R3는 질소원자와 함께 피페리디노, 피페라지노 또는 호모피페라지노일 수 없고;R1이 8-CONH2또는 8-CN일때, R2및R3가 모두 프로필일 수는 없으며; R1,R4및R5가 수소이고, R2및R3중 하나가 수소일때, 다른 하나는 에테닐일 수 없다.
  2. 제1항에 있어서, R1이 -CONR7R8,-(CO)het 및 - het 그룹으로부터 선택된 화합물.
  3. 제2항에 있어서, R1이 -het이고 8번 위치에 있는 화합물.
  4. 제3항에 있어서, 8-(옥사졸-5-일)-1,2,3,4-테트라하이드로-2,N,N-디-n-프로필아미노나프탈렌 및 그의 염산염과 8-(-3-브로모-이소옥사졸-5-일-1,2,3,4-테트라하이드로-2,N,N-디-n-프로필아미노나프탈렌 및 그의 염산염으로 이루어진 그룹으로부터 선택된 화합물.
  5. 제1항에 있어서, R이 수소와 할로겐 그룹으로부터 선택된 화합물.
  6. 제5항에 있어서, 5-플루오로-8-메톡시-1,2,3,4-테트라하이드로-2,N,N-디-n-프로필나프탈렌및 그의 말레산염, 5-플루오로-8-하이드록시-1,2,3,4-테트라하이드로-2,N,N-디-n-프로필나프탈렌 및 5- 플루오로-1,2,3,4-테트라하이드로-2,N,N-디-n-프로필아미노나프탈렌-8-카복스아미드로 이루어진 그룹으로부터 선택된 화합물.
  7. 제2항에 있어서, R1이 -CONR7R8이고 8번 위치에 있는 화합물.
  8. 제7항에 있어서, 1,2,3,4-테트라하이드로-2-N-n-프로필아미노나프탈렌-8-일-카복스아미드 및 그의 염산염, 1,2,3,4-테트라하이드로-2-N,N-디프로필아미노나프탈렌-8-일-카복스아미드 및 그의 염산염, 1,2,3,4-테트라하이드로-2-N-n-프로필-2-N-사이클로 프로필메틸아미노나프탈렌-8-일-카복스아미드, 1,2,3,4-테트라하이드로-2-N-n-프로필-2-N(4-(2,3-디하이드로-1,1-디옥소-3-벤조이소티아졸릴)부틸)아미노 나프탈렌-8-일-카복스아미드, 1,2,3,4-테트라하이드로-2--N-알릴아미노나프탈렌-8-일-카복스아미드 및 그의 말레산염, 1,2,3,4-테트라하이드로-2-N,N-디사이클로프로필 아미노나프탈렌-8-일-카복스아미드 및 1,2,3,4-테트라하이드로-2-N-사이클로프로필메틸-8-일-카복스아미드 및 그의 말레산염, 및 1,2,3,4-테트라하이드로-2-N-n-프로필-2N-트리메틸실릴-메틸아미노나프탈렌-8-일 -카복스아미드로 이루어진 그룹으로 부터 선택된 화합물.
  9. 제8항에 있어서, 1,2,3,4-테트라하이드로-2N-사이클로프로필메틸-2-N-n-프로필아미노나프탈렌-8-카복스아미드인 화합물.
  10. 제7항에 있어서, -CONR7R8이 N-알킬아미노카보닐인 화합물.
  11. 제10항에 있어서, 1,2,3,4-테트라하이드로-2-N,N-디-n-프로필아미노나프탈렌-8-일-N-벤질카복스아미 및 그의 말레산염,1,2,3,4-테트라하이드로-2,N,N-디사이클로프로필메틸 아미노나프탈렌-8-일-N-메틸카복스아미드, 및 1,2,3,4-테트라하이드로-2-N-사이클로프로필메틸아미노 나프탈렌-8-일-N-메틸카복스아미드로 이루어진 그룹으로부터 선택된 화합물.
  12. 제11항에 있어서, 1,2,3,4-테트라하이드로-2-N,N-디-프로필아미노나프탈렌-8-일-N-메틸카복스아미드인 화합물.
  13. 제2항에 있어서, R1이 -(CO)het이고 8번 위치에 있는 화합물
  14. 제13항에 있어서, (1,2,3,4-테트라하이드로-2-N,N-디사이클로프로필메틸아미노나프탈렌-8-일)(2-피롤)케톤 및 ((1,2,3,4-테트라하이드로-2-N-사이클로프로메틸-2-N(1-페닐-2-이미다졸리돈-3-일)아미노나프탈렌-8-일)(2-피롤)케톤으로 이루어진 그룹으로부터 선택된 화합물
  15. 제1항에 있어서, R2및 R3가 결합된 질소 고리와 함께인 화합물.
  16. 제15항에 있어서,시스2,6-디메틸-4-(1,2,3,4-테트라하이드로-8-메톡시-2-나프탈레닐)-모르폴리,트랜스2,6-디메틸-4-(1,2,3,4-테트라하이드로-8-메톡시-2-나프탈레닐)-모르폴리, 4-(1,2,3,4-테트라하이드로-8-메톡시-2-나프탈레닐)-티오모르폴린 및 그의 염산염, 7-(헥사하이드로-1(2H)-아조시닐)-5,6,7,8-테트라하이드로-1-나트탈렌올 및 그의 염산염, 7-(헥사하이드로-1(2H)-아조시닐)-1-메톡시-5,6,7,8-테트라하이드로나프탈렌 및 그의 염산염 및 2-(1-피롤리디닐)-1,2,3,4-테트라하이드로나프탈렌 및 그의 염산염으로 이루어진 그룹으로부터 선택된 화합물.
  17. 제1항에 있어서, R4가 -(C1-C8)알킬 -(C3-C8)알케닐, -(CH2)m-(C3-C8)사이클로알킬, -(CH2)m-OR6(이때, R6는 제1항에서 정의한 바와 같다)로 이루어진 그룹으로부터 선택된 화합물.
  18. 제17항에 있어서,트랜스-1,2,3,4-테트라하이드로-8-메톡시-1-(2-프로페닐)-N-프로필-2-나프탈렌아민 및 그의 염산염,시스-1,2,3,4-테트라하이드로-8-메톡시-1-(2-프로페닐)-N,N-디프로필-2-나프탈렌아민 및 그의 염산염,시스-1,2,3,4-테트라하이드로-8-메톡시-1-(2-프로페닐)-N-프로필-2-나프탈렌아민 및 그의 염산염,시스-1,2,3,4-테트라하이드로-8-메톡시-N,1-디프로필-2-나프탈렌아민 및 그의 염산염,시스-1,2,3,4-테트라하이드로-8-하이드록시-N,1-디프로필-2-나프탈렌아민 그의 염산염,시스-1,2,3,4-테트라하이드로-8-하이드록시-N,N,1-트로프로필-2-나프탈렌아민 및 그의 염산염,시스-1,2,3,4-테트라하이드로-8-메톡시-N,N,1-트리프로필-2-나프탈렌아민 및 그의 염산염,시스-1,2,3,4-테트라하이드로-8-메톡시-N,1-디-2-프로페닐-2-나프탈렌아민 및 그의 염산염,트랜스-1,2,3,4-테트라하이드로-8-메톡시-N,1-디-2-프로페닐-2-나프탈렌아민 및 그의 염산염,시스-1,2,3,4-테트라하이드로-8-메톡시-1-사이클로프로필메틸-N-프로필-2-나프탈렌아민 및 그의 염산염,트랜스-1,2,3,4-테트라하이드로-8-메톡시-1-사이클로프로필메틸-N-프로필-2-나프탈렌아민 및 그의 염산염,시스-1,2,3,4-테트라하이드로-8-메톡시-1-N,1-비스-사이클로프로필메틸-2-나프탈렌아민 및 그의 염산염,시스-1,2,3,4-테트라하이드로-8-메톡시-1-(2-프로페닐)-N-사이클로프로필메틸-2-나프탈렌아민 및 그의 염산염,트랜스-1,2,3,4-테트라하이드로-8-메톡시-N,1-비스-사이클로프로필메틸-2-나프탈렌아민 및 그의 염산염,트랜스-1,2,3,4-테트라하이드로-8-메톡시-1-(2-프로페닐)-N-사이클로필메틸-2-나프탈렌아민 및 그의 염산염,트랜스-1,2,3,4-테트라하이드로-1-(2-프로페닐)-N-프로필-2-나프탈렌아민 및 그의 염산염,시스-1,2,3,4-테트라하이드로-1-(2-프로페닐)-N-프로필-2-나프탈렌아민 및 그의 염산염,시스-1,2,3,4-테트라하이드로-5-메톡시-1-(2-프로페닐)-N-프로필-2-나프탈렌아민 및 그의 염산염,트랜스-1,2,3,4-테트라하이드로-5-메톡시-1-(2-프로페닐)-N-프로필-2-나프탈렌아민 및 그의 염산염,시스-1,2,3,4-테트라하이드로-1-하이드록시메실-8-메톡시-1-N-프로필-2-나프탈렌아민 및 그의 염산염,시스1-(사이클로프로필메틸)-1,2,3,4-테트라하이드로-8-메톡시-1-(2-프로페닐)-N-프로필-2-나프탈렌아민 및 그의 염산염,트랜스1-(사이클로프로필메틸)-1,2,3,4-테트라하이드로-8-메톡시-N-2-프로페닐-2-나프탈렌아민 및 그의 염산염,시스-1,2,3,4-테트라하이드로-8-메톡시-1-하이드록시메틸-n-2-프로페닐-2-나프탈렌아민 및 그의 염산염,트랜스-1,2,3,4-테트라하이드로-8-메톡시-1-하이드록시메틸-N-2-프로페닐-2-나프탈렌아민 및 그의 염산염, 및시스-1,2,3,4-테트라하이드로-8-하이드록시-N,1-디-(2-프로페닐)-2-나프탈렌아민 및 그의 염산염으로 이루어진 그룹으로 부터 선택된 화합물.
  19. 제1항에 있어서,R1이 8-메톡시이고, R5가 (C2-C8)알케닐이며, R2및R3가 제1항에서 정의한 바와 같은 화합물.
  20. 제19항에 있어서,시스-1,2,3,4-테트라하이드로-8-메톡시-N-3-디-프로페닐-2-나프탈렌아민 및 그의 염산염,트랜스-1,2,3,4-테트라하이드로-8-메톡시-N-3-디-프로페닐-2-나프탈렌아민 및 그의 염산염,시스-1,2,3,4-테트라하이드로-8-메톡시-3-프로페닐-N-n-프로필-2-나프탈렌아민 및 그의 염산염,및트랜스-1,2,3,4-테트라하이드로-8-메톡시-3-프로페닐-N-n-프로필-2-나프탈렌아민 및 그의 염산염으로 이루어진 그룹으로 부터 선택된 화합물.
  21. 제1항에 있어서, R1이 제1항에서 정의한 바와 같고, R2및R3가 동일하거나 상이하고, 수소, C3-C5알케닐 및R3-R8알키닐로 이루어진 그룹으로부터 선택되나, 단 R2및 R3중의 하나가 수소일 때, 다른 하나는 1-프로페닐일 수 없는 화합물.
  22. 제21항에 있어서, 1,2,3,4-테트라하이드로-8-메톡시-N,N-디-2-프로페닐-2-나프탈렌아민 및 그의 염산염 1,2,3,4-테트라하이드로-8-메톡시-N-2-프로피닐-2-나프탈렌아민 ,1,2,3,4-테트라하이드로-8-메톡시-N,2-프로피닐-2-나프탈렌아민 및 그의 염산염, 1,2,3,4-테트라하이드로-8-메톡시-N,N-디-2-프로페닐-2-나프탈렌아민 및 그의 염산염, N-에틸-1,2,3,4-테트라하이드로-8-메톡시-N-(2-메틸-2-프로페닐)-2-나프탈렌아민 및 그의 염산염, 1,2,3,4-테트라하이드로-8-하이드록-N-2-프로페닐-2-나프탈렌아민 및 그의 염산염, 7-{(사이클로프로필메틸)프로필아미노}-5,6,7,8-테트라하이드로-1-나프탈렌카보니트릴 및 그의 (E)-2-부텐디오에이트, 1,2,3,4-테트라하이드로-8-메톡시-N-(2-메틸-2-프로페닐)-2-나프탈렌아민 및 그의 염산염, 1,2,3,4-테트라하이드로-N-프로페닐-2-나프탈렌아민 및 그의 염산염, 1,2,3,4-테트라하이드로-N-프로페닐-나프탈렌아민 및 그의 염산염, 1,2,3,4-테트라하이드로-8-메톡시-N-메틸-N-2-프로페닐-2-나프탈렌아민 및 그의 염산염, 1,2,3,4-테트라하이드로-8-메톡시-N-메틸-N-(2-메틸-2-프로페닐)-2--나프탈렌아민 및 그의 염산염, 1,2,3,4-테트라하이드로-N-디-2-프로피닐-2-2-나프탈렌아민 및 그의 염산염, 1,2,3,4-테트라하이드로-8-하이드록시-N,N-디-2-프로페닐-2-나프탈렌아민 및 그의 염산염, 1,2,3,4-테트라하이드로-8-메톡-N-메틸-N-2-프로페닐-2-나프탈렌아민 및 그의 염산염, 1,2,3,4-테트라하이드로-N,N-디-2-프로페닐-2-나프탈렌아민 및 그의 염산염, 1,2,3,4-테트라하이드로-8-메톡시-1-하이드록시메틸-N-2-프로페닐-2-나프탈렌아민 및 그의 염산염,시스-1,2,3,4-테트라하이드로-8-메톡시-N-메틸-1-하이드록시메틸-N-n-프로필-2-나프탈렌아민 및 그의 염산염, N-(사이클로프로필메틸)-1,2,3,4-테트라하이드로-8-메톡시-2-나프탈렌아민 및 그의 염산염,N-(사이클로프로필메틸)-1,2,3,4-테트라하이드로-2-나프탈렌아민 및 그의 염산염, N-(사이클로프로필메틸)-1,2,3,4-테트라하이드로-8-하이드록시-2-나프탈렌아민 및 그의 염산염, 및 1,2,3,4-테트라하이드로-N-메틸-N-n-프로필-2-나프탈렌아민 및 그의 염산염으로 이루어진 그룹으로부터 선택된 화합물.
  23. 제22항에 있어서, 1,2,3,4-테트라하이드로-N-2-프로페닐-2-나프탈렌아민 및 그의 염산염으로 이루어진 그룹으로부터 선택된 화합물.
  24. 제22항에 있어서, 1,2,3,4-테트라하이드로-8-메톡시-N-2-프로페닐-2-나프탈렌아민 및 그의 염산염으로 이루어진 그룹으로부터 선택된 화합물.
  25. 제22항에 있어서, 1,2,3,4-테트라하이드로-8-메톡시-N-메틸-N-2-프로페닐-2-나프탈렌아민인 화합물.
  26. 제1항에 있어서, 하기 일반식(V)의 화합물:
    상기식에서, R1,R2,R3및 R4는 제1항에 있어서 정의한 바와 같다.
  27. 제26항에 있어서, 1,2,3,4-테트라하이드로-8-메톡시-N-(2-프로페닐)-N-n-2-나프탈렌아민및 그의 염산과 1,2,3,4-테트라하이드로-1-메티닐-8-메톡시-N-메틸-N-n-프로필-2-나프탈렌아민 및 그의 염산염으로 이루어진 그룹으로부터 선택된 화합물.
  28. 제1항에 있어서, R이 수소이고, -CF5, -SO2R7R8및 5-옥사졸릴로 이루어진 그룹으로부터 선택되며, R2및 R3가 동일 하거나 또는 상이이고, 수소 및 (C1-C8)알킬로 이루어진 그룹으로부터 선택된 화합물.
  29. 제1항에 있어서, (+)-8-트리플루오로메틸-2N-n-프로필아미노테트랄린, (-)-8-트리플루오로메틸-2N-n-플로필아미노테트랄린, (+)-8-트리플루오로메틸-2-N,N-디-n-프로필아미노테트랄린, (-)-8-트리플루오로메틸-2-N,N-디-n-프로필아미노테트랄린, 8-브로모-2-N,N-디-n-플로필아미노테트랄린, 8-포밀-2-N,N-디-n-플로필아미노테트랄린, 8-(5-옥사졸릴)-2-N,N-디-n-플로필아미노테트랄린, 8-아미노설포닐-2N-n-플로필아미노테트랄린,8-아미노설포닐-2-(N-알릴)테트랄린,8-아미노설포닐-2-(N,N-디프로필아미노)테트랄린,및 8-아미노설포닐-2-(N-(3-페닐프로필)아미노테트랄린으로 이루어진 그룹으로부터 선택된 화합물.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019910701735A 1989-05-31 1990-05-22 치료학적으로 유용한 2-아미노테트랄린 유도체 KR100195656B1 (ko)

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KR100195656B1 (ko) 1999-06-15
ATE172712T1 (de) 1998-11-15
AU654653B2 (en) 1994-11-17
NO914714L (no) 1991-11-29
ES2123500T3 (es) 1999-01-16
HUT61719A (en) 1993-03-01
EP0476016A1 (en) 1992-03-25
WO1990015047A1 (en) 1990-12-13
CA2051399C (en) 2003-12-30
DK0476016T3 (da) 1999-07-05
HU905095D0 (en) 1992-02-28
US6331636B1 (en) 2001-12-18
JPH04505618A (ja) 1992-10-01
NO914714D0 (no) 1991-11-29
JP2785879B2 (ja) 1998-08-13
DE69032725T2 (de) 1999-04-08
EP0476016B1 (en) 1998-10-28
NO176437B (no) 1994-12-27
RU2086535C1 (ru) 1997-08-10
FI915656A0 (fi) 1991-11-29
NO176437C (no) 1995-04-05
AU5822190A (en) 1991-01-07
CA2051399A1 (en) 1990-12-01
DE69032725D1 (de) 1998-12-03

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