KR920016444A - 이미다졸, 트리아졸 및 테트라졸 유도체 - Google Patents

이미다졸, 트리아졸 및 테트라졸 유도체 Download PDF

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KR920016444A
KR920016444A KR1019920001592A KR920001592A KR920016444A KR 920016444 A KR920016444 A KR 920016444A KR 1019920001592 A KR1019920001592 A KR 1019920001592A KR 920001592 A KR920001592 A KR 920001592A KR 920016444 A KR920016444 A KR 920016444A
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ethylamine
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베이커 레이몬드
지. 매타사 빅터
스트리트 레슬리 제이
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앨런 허스케쓰
머크 샤프 앤드 돔 리미티드
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Abstract

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Description

이미다졸, 트리아졸 및 테트라졸 유도체
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 일반식(Ⅰ)의 화합물, 또는 이의 염 또는 예비약제.
    (Ⅰ)
    상기식에서, 점선은 5원환의 임의의 위치에 존재하는 두개의 비-인접한 이중 결합을 나타내고, V, W, X, Y, 및Z는 이들중 두개 내지 네개는 질소이고 나머지는 탄소이며, 단, 이들중 두개가 질소이고 나머지가 탄소인 경우에, 상기한 두개의 질소원자들은 5원환중 비-인접한 위치에 존재하며, A1은 수소, 탄화수소, 헤테로사이클릭그룹, 할로겐, 시아노,트리플루오로메틸, 또는 일반식 ORx, -SRx,-NRxRy, -NRxCORy, -NRxCO2Ry, -NRxSO2Ry또는 -NRxCTNRxRy[여기서, Rx및Ry는 독립적으로 수소, 탄화수소 또는 헤테로사이클릭 그룹을 나타내거나, 이들은 함께 C2-6알킬렌 그룹을 형성하며;Rx는 수소, 탄화수소 또는 헤테로사이클릭 그룹이고;T는 산소, 황 또는 일반식=NG(여기서, G는 탄화수소, 헤테로사이클릭 그룹 또는 전자-구성인 그룹이다)의 그룹이다]의 그룹이고, A2는 V,W,X,Y,및 Z중 네개가 질소이고 다른 하나가 탄소일 경우에는 비-결합된 전자쌍이고, V,W,X,Y및Z중 두개 또는 세개가 질소이고 나머지가 탄소일 경우에는 수소, 탄화수소, 헤테로사이클릭 그룹, 할로겐, 시아노, 트리플루오로메틸, 또는 일반식ORx, -SRx, -NRxRy,-NRxCORy, -NRxCO2Ry, -NRxSO2Ry또는 -NRxCTNRxRy(여기서, Rx,Ry,Rx및 T는 A1에 대해서 상기한 바와 같다)의 그룹이며, E는 하나의 결합 또는 탄소수 1내지 4의 직쇄 또는 측쇄 알킬렌쇄이고,
    F는 일반식[여기서, U는 질소 또는 C-R2이고;B는 산소, 황
    또는 N-R3이며;R1은 -CH2CHR4NR6R7또는 일반식
    또는의 그룹이고;R2,R3,R4,R5,R6및 R7은 독립적으로 수소 또는 C1-6
    알킬이다]의 그룹이다.
  2. 제1항에 있어서, 일반식(ⅡA)의 화합물, 및 이의 염 및 예비 약제.
    상기식에서, X1질소 또는 A12-C이고, n은 0,1,2또는 3이며, B1은 산소, 황 또는 N-R13이고, A11및 A12는 독립적으로 임의로 치환될수 있는 C1-6알킬, C2-6알케닐, C2-6알키닐, C3-7사이클로알킬, 아릴, 아릴(C1-6)알킬, C3-7헤테로사이클로알킬, 헤테로알킬, 헤테로아릴 또는 헤테로아릴(C1-6)알킬;또는 수소, 할로겐, 시아노, 트리플루오로메틸, C1-6알콕시, C1-6알킬티오 또는 일반식-NRxRy(여기서, Rx및Ry는 독립적으로 수소, 탄화수소 또는 헤테로사이클릭 그룹이거나, 이들은 함께 C2-6알킬렌 그룹을 형성한다)의 그룹이며, R12,R13,R14,R16,및R17은 독립적으로 수소 또는 C1-6알킬이다.
  3. 제1항에 있어서, 일반식(ⅡB)의 화합물, 및 이의 염 및 예비약제.
    상기식에서, Y1질소 또는 A22-C이고, n은 0,1,2또는 3이며, B2는 산소, 황 또는 N-R23이고, A21및A22는 독립적으로 임의로 치환될 수 있는 C1-5알킬, C2-6알케닐, C2-6알키닐, C3-7사이클로알킬, 아릴, 아릴(C1-6)알킬, C3-7헤테로사이클로알킬, 헤테로아릴 또는 헤테로아릴(C1-6)알킬;또는 수소, 할로겐, 시아노, 트리플루오로메틸, C1-6알콕시, C1-6알킬티오 또는 일반식-NRxRy(여기서, Rx및Ry는 독립적으로 수소, 탄화수소 또는 헤테로사이클릭 그룹을 나타내거나, 이들은 함께 C2-6알킬렌 그룹을 형성하다)의 그룹이며, R23,R23,R24,R26및R27은 독립적으로 수소 또는 C1-6알킬이다.
  4. 제1항에 있어서, 일반식(ⅡC)의 화합물, 및 이의 염 및 예비약제.
    상기식에서, Y2은 질소 또는A32-C이고, Z1은 질소 또는 CH이며, n은 0,1,2또는 3이고, B3는 산소, 황 또는 N-R33이고, A31및 A32는 독립적으로 임의로 치환될 수 있는 C1-6알킬, C2-6알케닐, C2-6알키닐, C3-7사이클로알킬, 아릴, 아릴(C1-6)알킬, C3-7헤테로사이클로알킬, 헤테로아릴 또는 헤테로아릴(C1-6)알킬;또는 수소, 할로겐, 시아노, 트리플루오로메틸, C1-6알콕시, C1-6알킬티오 또는 일반식 -NRxRy(여기서, Rx및 Ry는 독립적으로 수소, 탄화수소 또는 헤테로사이클릭 그룹을 나타내거나, 이들은 함께 C2-6알킬렌 그룹을 형성한다)의 그룹이며, R31은 일반식 -CH2CHR34NR36R37의 그룹 또는 일반식
    또는의 그룹이며
    R32,R33,R34,R35,R36및 R37은 독립적으로 수소 또는 C1-6알킬이다.
  5. 제1항에 있어서, 일반식(ⅡD)의 화합물, 및 이의 염 및 예비약제.
    상기식에서, W1은 질소 또는 C-A42이고, n은 0,1,2또는 3이며, B4는 산소, 황 또는 N-R43이고, A41및 A42는 독립적으로 임의로 치환될 수 있는 C1-6알킬, C2-6알케닐, C2-6알키닐, C3-7사이클로알킬, 아릴, 아릴(C1-6)알킬, C3-7헤테로사이클로알킬, 헤테로아릴 또는 헤테로아릴(C1-6)알킬;또는 수소, 할로겐, 시아노, 트리플루오로메틸, C1-6알콕시, C1-6알킬티오 또는 일반식-NRxRy(여기서,Rx및 Ry는 독립적으로 수소, 탄화수소 또는 헤테로사이클릭 그룹이거나, 이들은 함께 C2-6알킬렌 그룹을 형성한다)의 그룹이며, R41은 일반식 -CH2CHR44NR46R47의 그룹 또는 일반식
    또는의 그룹이고
    R42,R43,R44,R45,R46및R47은 독립적으로 수소 또는 C1-6알킬이다.
  6. 제1항에 있어서, 2-[5-(2-벤질테트라졸-5-일메틸)-1H-인돌-3-일]에틸아민;2-[5-(1-벤질테트라졸-5-일메틸)-1H-인돌-3-일]에틸아민;N,N-디메틸-2-[5-(1-메틸테트라졸-5-일메틸)-1H-인돌-3-일]에틸아민;N,N-디메틸-2-[5-(2-메틸테트라졸-5-일메틸)-1H-인돌-3-일]에틸아민;N,N-디메틸-2-[5-(1,2,4-트리아-1-일메틸)-1H-인돌-3-일]에틸아민;N,N-디메틸-2-[5-(테트라졸-2-일메틸)-1H-인돌-3-일]에틸아민;N,N-디메틸-2-[5-(테트라졸-1-일메틸)-1H-인돌-3-일]에틸아민;N,N-디메틸-2-[5-(1-메틸-1,2,4-트라아졸-5-일메틸)-1H-인돌-3-일]에틸아민;N,N-디메틸-2-[5-(1-메틸-1,2,4-트리아졸-3-일메틸)-1H-인돌-3-일]에틸아민;N,N-디메틸-2-[5-(1,2,3-트리아졸-1-일메틸)-1H-인돌-3-일]에틸아민;3-(2-아미노에틸)-5-(1-메틸테트라졸-5-일)벤조[b]티오펜;3-(2-아미노에틸)-5-(2-메틸테트라졸-5-일)벤조[b]티오펜;3-[2-(N,N-디메틸아미노)에틸]-5-(2-메틸테트라졸-5-일)벤조[b]티오펜;N,N-디메틸-2-[5-(2-메틸이미다졸-1-일메틸)-1H-인돌-3-일]에틸아민;N,N-디메틸-2-[5-(이미다졸-1-일메틸)-1H-인돌-3-일]에틸아민;N,N-디메틸-2-[5-(2-메틸이미다졸-1-일)-1H-인돌-3-일]에틸아민;N,N-디메틸-2-[5-(2-에틸테트라졸-5-일메틸)-1H-인돌-3-일]에틸아민;N,N-디메틸-2-[5-(1-에틸테트라졸-5-일메틸)-1H-인돌-3-일]에틸아민;N,N-디메틸-2-[5-(1,2,4-트리아졸-1-일)-1H-인돌-3-일]에틸아민;1-메틸-4-[5-(2-메틸이미다졸-1-일)-1H-인돌-3-일]피페리딘;1-메틸-4-[5-(1,2,4-트리아졸-1-일메틸)-1H-인돌-3-일]피페리딘;4-[5-(2-메틸이미다졸-1-일)-1H-인돌-3-일]피페리딘;4-[5-(1,2,4-트리아졸-1-일메틸)-1H-인돌-3-일]피페리딘;3-[5-(2-메틸이미다졸-1-일)-1H-인돌-3-일]피롤리딘;1-메틸-3-[5-(2-메틸이미다졸-1-일)-1H-인돌-3-일]피롤리딘;4-[5-(이미다졸-1-일)-1H-인돌-3-일]피페리딘;4-[5-(1,2,3-트리아졸-1-일)-1H-인돌-3-일]피페리딘;1-메틸-4-[5-(이미다졸-1-일)-1H-인돌-3-일]피페리딘;1-메틸-4-[5-(1,2,3-트리아졸-1-일)-1H-인돌-3-일]피페리딘;1-메틸-3-[5-(1,2,3-트리아졸-1-일)-1H-인돌-3-일]피페리딘;1-메틸-3-[5-(2-메틸이미다졸-1-일메틸)-1H-인돌-3-일]피롤리딘;1-메틸-3-[5-(이미다졸-1-일)-1H-인돌-3-일]피롤리딘;1-메틸-3-[5-(1,2,4-트리아졸-1-일메틸)-1H-인돌-3-일]피롤리딘;1-메틸-3-[5-(이미다졸-1-이메틸)-1H-인돌-3-일]피롤리딘;N,N-디메틸-2-[5-(2-아미노이미다졸-1-일)-1H-인돌-3-일]에틸아민;N,N-디메틸-2-[5-(2-아미노이미다졸-1-일메틸)-1H-인돌-3-일]에틸아민;N-메틸-2-[5-(1,2,4-트리아졸-1-일메틸)-1H-인돌-3-일]에틸아민;및 이들의 염 및 예비약제중에서 선택된 화합물.
  7. 제1항 내지 제6항 중 어는 한 항에 따른 화합물을 약제학적으로 허용되는 담체 또는 부형제와 혼합된 상태로 포함하는 약제학적 조성물.
  8. 치료학적 용도로 사용하기 위한 제1항 내지 제6항 중 어느 한 항에 따른 화합물.
  9. 5-HT1-형 수용체의 선택적 효능제가 요구되는 임상적 질환을 치료하고/하거나 예방하기 위한 약제를 제조하기 위한 제1항 내지 6항 중 어느 한 항에 따른 화합물의 용도.
  10. (A)일반식(Ⅲ')의 카복실산의 반응성 유도체를 일반식(Ⅲ)또는 (Ⅳ)의 화합물 또는 이의 염과 반응시키거나, (B)일반식(ⅩⅣ)의 화합물을 음이온 A2-(여기서, A2는 제1항에서 정의한 바와 같다)을 제공하는 시약과 반응시키거나, (C)일반식(Ⅲ")의 알킨을 일반식(Ⅲ"')의 아지드로 사이클로부가반응시키거나, (D)일반식(Ⅳ')의 니트릴을 일반식(Ⅳ")의 아지드로 사이클로부가반응시키거나, (E)일반식(Ⅳ"')의 화합물을 염기의 존재하에서 일반식(XV)의 테트라졸 유도체와 반응시키거나, (F)일반식(Ⅴ')으 니트릴을 아지드화나트륨으로 사이클로부가반응시킨 후 무기산으로 산성화시키거나, (G) 일반식(X Ⅵ)의 화합물을 일반식(Ⅶ)의 화합물 또는 이의 카보닐-보호된 형태의 화합물과 반응시키고, 경우에 따라 표준 방법으로 N-알킬화시켜 잔기R3을 도입시키거나, (H)일반식(XXⅡ)의 화합물을 폐환반응시키고, 경우에 따라 표준방법으로 N-알킬화시켜 잔기R3을 도입시키거나,(I)일반식(XXV)의 화합물을 폐환반응시키고, 경우에 따라 그룹R21을 목적하는 그룹R1으로 전환시키고, (J)계속해서, 경우에 따라, 최초로 수득된 일반식(Ⅰ)의 화합물을 통상의 방법으로 다른 일반식(Ⅰ)의 화합물로 전환시킴을 특징으로 하여, 제1항 내지 제6항 중 어느 한 항에 따른 화합물을 제조하는 방법.
    (Ⅰ)
    Ra-CO2H (Ⅲ')
    (Ⅲ)
    (Ⅳ)
    (XⅣ)
    Ra-C=C-Rb(Ⅲ")
    Rc-N3(Ⅲ"')
    N=C-Rd(Ⅳ')
    Re-N3(Ⅳ")
    Re-L (Ⅳ"')
    N≡C-E-F
    상기식에서,A1,A2,E,F,V,W,X,Y,Z 및 점선은 제1항에서 정의한 바와 같고, Ra,Rb및 Rc는 이들중 하나는 일반식 A1의 그룹이고, 다른 하나는 일반식A2의 그룹이며,또다른 하나는 일반식 -E-F의 그룹이고, Rd및Re는 이들 중 하나는 일반식 A1의 그룹이며, 다른 하나는 일반식 -E-F의 그룹이고, Hal은 할로겐을 나타내며, Va,Wa,Xa,Ya및Za는 이들 중 두개의 그룹은 탄소이고 나머지는 질소이며, 이들중 하나에 그룹 Hal이 결합되어 있으며, R11은 제1항에서 정의한 그룹 R1에 상응하거나, 일반식-CH2CHR4D1(여기서, R4는 제1항에서 정의한 바와같고, D1은 용이하게 치환시킬 수 있는 그룹이다)의 그룹이고, D2는 용이하게 치환시킬 수 있는 그룹이며, Ba는 산소 또는 황이고, R21은 제1항에서 정의한 바와 같은 그룹 R1에 상응하거나 이의 전구체그룹을 나타낸다.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019920001592A 1991-02-01 1992-02-01 이미다졸, 트리아졸 및 테트라졸 유도체, 및 이를 포함하는 약제학적 조성물 KR100212111B1 (ko)

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