KR950702962A - 도파민 D₃수용체 길항제인 5-(2-옥시페닐)-피롤 유도체(5-(2-Oxyphenyl)-Pyrrole Derivatives as Dopamine D₃Receptor Antagonists) - Google Patents

도파민 D₃수용체 길항제인 5-(2-옥시페닐)-피롤 유도체(5-(2-Oxyphenyl)-Pyrrole Derivatives as Dopamine D₃Receptor Antagonists) Download PDF

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KR950702962A
KR950702962A KR1019950700431A KR19950700431A KR950702962A KR 950702962 A KR950702962 A KR 950702962A KR 1019950700431 A KR1019950700431 A KR 1019950700431A KR 19950700431 A KR19950700431 A KR 19950700431A KR 950702962 A KR950702962 A KR 950702962A
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pyrrole
methoxyphenyl
ethylsulfonyl
ethyl
optionally substituted
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지오프레이 스템프
마이클 스튜와트 하들리
데이비드 죤 나쉬
크리스토퍼 노베르트 죤슨
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데이비드 로버츠
스미스클라인 비참 피엘씨
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Abstract

식(I)의 화합물:
(상기식에서, R1은 C1-4알킬이고, R2, R3, R4및 R5각각은 독립적으로 수소, 할로겐, C1-4알킬, C1-4알콕시, C1-4알콕시C1-4알킬, C1-4알킬술포닐, 트리플루오로메틸술포닐, 임의로 치환된 아릴술포닐 임의로 치환된 헤테로아릴술포닐, 니트로, 시아노, 아미노, 모노- 또는 디-알킬아미노, 트리플루오로메틸, 트리플루오로메톡시, 히드록실, 히드록시알킬, C1-4알킬티오, C1-4알카노일, C1-4알콕시카보닐, 아미노술포닐, 알킬아미노술포닐 또는 디아킬아미노술포닐이거나, 또는 R1및 R2는 함께 임의로 한 개나 또는 두개의 C1-4알킬기로 치환될 수 있는 연결 사슬인 -(CH2)mOp(여기서, m은 2 내지 4이며 p는 0 또는 1)를 형성하며, Y는 하기식으로부터 선택된 기를 나타낸다.
상기 식에서 R6및 R7은 독립적으로 수소, C1-6알킬, 임의로 치환된 아릴 C1-6알킬 또는 임의로 치환된 헤테로아릴C1-6알킬이고, R8는 C1-6알킬, C3-6알케닐 또는 C3-6시클로알킬C1-4알킬이며, R9는 C1-6알킬, C3-6알케닐, C3-6시클로알킬C1-4알킬, 임의로 치환된 아릴 C1-4알킬 또는 임의로 치환된 헤테로아릴 C1-4알킬 또는 임의로 치환된 헤테로아릴C1-4알킬이거나, 또는 NR8R9(다만, NR8R9는 피페라진이 아님)는 헤테로시클릭 고리를 형성하며, R10은 C1-6알킬, C3-6알케닐, C3-6시클로알킬C1-4알킬, 임의로 치환된 아릴C1-4알킬 또는 임의로 치환된 헤테로아릴C1-4알킬이고, n은 1 내지 3을 나타낸다.) 또는 이들의 염은 도파민 D3수용체에 친화력을 가지며 정신질환의 치료에 유용하다.

Description

도파민 D3수용체 길항제인 5-(2-옥시페닐)-피롤 유도체(5-(2-Oxyphenyl)-Pyrrole Derivatives as Dopamine D3Receptor Antagonists)
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Claims (13)

  1. 식(I)의 화합물 또는 이들의 염.
    상기 식에서, R1은 C1-4알킬이고, R2, R3, R4및 R5각각은 독립적으로 수소, 할로겐, C1-4알킬, C1-4알콕시, C1-4알콕시C1-4알킬, C1-4알킬술포닐, 트리플루오로메틸술포닐, 임의로 치환된 아릴술포닐, 임의로 치환된 헤테로아릴술포닐, 임의로 치환된 아랄킬술포닐, 임의로 치환된 헤테로아랄킬술포닐, 니트로, 시아노, 아미노, 모노-또는 디-알킬아미노, 트리플루오로메틸, 트리플루오로메톡시, 히드록실, 히드록시알킬, C1-4알킬티오, C1-4알카노일, C1-4알콕시카보닐, 아미노술포닐, 알킬아미노술포닐 또는 디아킬아미노술포닐이거나, 또는 R1및 R2는 함께 임의로 한 개나 또는 두개의 C1-4알킬기로 치환될 수 있는 연결 사슬인 -(CH2)mOp(여기서, m은 2 내지 4이며 p는 0 또는 1)를 형성하며, Y는 하기식으로부터 선택된 기를 나타낸다.
    상기 식에서 R6및 R7은 독립적으로 수소, C1-6알킬, 임의로 치환된 아릴C1-6알킬 또는 임의로 치환된 헤테로아릴C1-6알킬이고, R8는 C1-6알킬, C3-6알케닐 또는 C3-6시클로알킬C1-4알킬이며, R9는C1-6알킬, C3-6알케닐, C3-6시클로알킬C1-4알킬, 임의로 치환된 아릴 C1-4알킬 또는 임의로 치환된 헤테로아릴 C1-4알킬이거나, 또는 NR8R9(다만, NR8R9는 피페라진이 아님)는 헤테로시클릭 고리를 형성하며, R10은 C1-6알킬, C3-6알케닐, C3-6시클로알킬C1-4알킬, 임의로 치환된 아릴C1-4알킬 또는 임의로 치환된 헤테로아릴C1-4알킬이고, n은 1 내지 3을 나타낸다.
  2. 제1항에 있어서, R1이 메틸, 에틸 또는 이소프로필인 화합물.
  3. 제1항 또는 2항에 있어서, R2내지 R5중의 적어도 하나는 수소이며, 다른 치환체들은 할로겐, C1-2알킬, C1-2알콕시, C1-4알킬술포닐, 페닐술포닐, CF3, CF3O 및 디알킬아미노술포닐로부터 선택된 것인 화합물.
  4. 제1항 내지 3항 중의 하나의 항에 있어서, Y가 R6는 수소, R7는 수소 또는 수소 또는 메틸을 나타내는 그룹(a)인 화합물.
  5. 제1항 내지 4항 중의 한 항에 있어서, Y가 R8는 C1-3알킬이고 R9는 C1-4알킬, 시클로프로필메틸, 알릴 또는 임의로 치환된 페닐메틸이거나 또는 -NR8R9가 전체적으로 또는 부분적으로 포화된 5 내지 8원 헤테로시클릭 고리를 형성하며, 임의로 C1-3알킬렌 다리를 포함하는 그룹(a)를 나타내는 화합물.
  6. 제1항 내지 3항 중의 하나의 항에 있어서, Y가 R10는 C1-4알킬, 시클로프로필메틸, 알릴 또는 벤질을 나타내는 그룹 (b)인 화합물.
  7. 제1항에 있어서, 다음중에서 선택된 화합물 또는 이들의 염.
    2-(3,5-디브로모-2-메톡시페닐) -5-(1-피페리디닐메틸)-1H-피롤, 2-(5-에틸술포닐-2-메톡시페닐)-5-(1-피페리디닐메틸)-1H-피롤, 2-(1-에틸-2-헥사히드로아제피닐)-5-(5-에틸술포닐-2-메톡시페닐)-1H-피롤, 2-(5-클로로-2-메톡시페닐)-5-(1-피페리디닐메틸)-1H-피롤, 2-(2,3-디메톡시페닐)-5-(1-피페리디닐메틸)-1H-피롤, 2-(5-에틸술포닐-2-메톡시페닐-5-[(2-(1,2,3,4-테트라히드로이소퀴놀리닐)-메틸]-1H-피롤, 2-(5-에틸술포닐-2-메톡시페닐)-5-(1-피롤리디닐메틸)-1H-피롤, 2-(5-에틸술포닐-2-메톡시페닐)-5-(1-헥사히드로아제피닐메틸)-1H-피롤, 2-(5-에틸술포닐-2-메톡시페닐)-5-(1-(2-메틸피페리디닐)-메틸)-1H-피롤, 2 - (5-에틸술포닐-2-메톡시페닐)-5-(1-(시스-2,6-디메틸-피페리디닐)메틸)-1H-피롤, 2-(5-애틸술포닐-2-메톡시페닐)-5-(1-헵타메틸렌-이미닐메틸)-1H-피롤, 2-(5-에틸술포닐-2-메톡시페닐)-5-디메틸아미노메틸-1H-피롤, 2-(5-에틸술포닐-2-메톡시페닐)-5-디프로필아미노메틸-1H-피롤, 2-(5-에틸술포닐-2-메톡시페닐)-5-디에틸아미노메틸-1H-피롤, 2-(1-에틸-2-피페리디닐)-5-(5-에틸술포닐-2-메톡시페닐)-1H-피롤, 5-(6-클로로-벤조[b]피란-8-일)-2-(1-피페리디닐메틸)-1H-피롤, 2-(3-브로모-5-에틸술포닐-2-메톡시페닐)-5-(1-피페리디닐메틸)-1H-피롤, 2-(3,5-디브로모-2-이소프로폭시페닐)-5-(1-피페리디닐메틸)-1H-피롤, 2-(3,5-디브로모-2-이소프로폭시페닐)-5-[1-(1-피페리디닐)-에틸]-1H-피롤, 2-(3,5-디브로모-2-이소프로폭시페닐)-5-(N-벤질-N-에틸)아미노메틸-1H-피롤, 2-(3,5-디브로모-2-에톡시페닐)-5-(1-피페리디닐메틸)-1H-피롤, 2-(3,5-디브로모-2-에톡시페닐)-5-[1-(1-피페리디닐)-에틸]-1H-피롤, 2-(1-(1-옥타히드로아조시닐)에틸)-5-(3,5-디브로모-2-메톡시페닐)-1H-피롤, 2-(3,5-디클로로-2-매톡시페닐)-5-(1-피페리디닐메틸)-1H-피롤, 2-(1-(1-피페리디닐)에틸)-5-(3,5-디브로모-2-메톡시페닐)-1H-피롤, 2-(5-에틸술포닐-2-메톡시페닐)-5-(N-벤질-N-에틸)-아미노메틸-1H-피롤, 2-(5-브로모-2-메톡시-3-메틸페닐)-5-(1-피페리디닐메틸)-1H-피롤, 2-(3-브로모-5-메틸술포닐-2-메톡시피닐)-5)[1-(1-피페리디닐)-에틸)-1H-피롤, 2-(3-브로모-5-에틸술포닐-메톡시페닐)-5-(N-벤질-N-에틸)-아미노메틸-1H-피롤, 2 - (2-메톡시-5-트리플루오로메틸페닐)-5-(1-피페리디닐메틸)-1H-피롤, 2-(2-메톡시-5-트리플루오로메톡시페닐)-5-(1-피페리디닐메틸)-1H-피롤, 2-(3,5-디아이오도-2-메톡시페닐)-5-(1-피페리디닐메틸)-1H-피롤, 2-(3,5-디아이오도-2-메톡시페닐)-5-[1-(1-피페리메틸)에틸]-1H-피롤, 2-(2,3-디메톡시-5-브로모페닐)-5-(1-피페리디닐메틸)-1H-피롤, 2-(2,3-디메톡시-5-브로모페닐)-5-[1-(1-피페리디닐)에틸]-1H-피롤, 2-(2-메톡시-5-페닐술포닐페닐)-5-(1-피페리디닐메틸)-1H-피롤, 2-(2-메톡시-5-페닐술포닐페닐)-5-[1-(1-피페리디닐)에틸]-1H-피롤, 2-(1-벤질-피페리디닐)-5-(5-에틸술포닐-2-메톡시페닐)-1H-피롤, 2-[(8-아자비시클로[3.2.1]옥탄-8-일)메틸]-5-(5-에틸풀포닐-2-메톡시페닐)-1H-피롤, 2-[(3-아자비시클로[3.2.1]노단-3-일)메틸]-5-(5-에틸풀포닐-2-메톡시페닐)-1H-피롤, 2-(3,5-디브로모-2-메톡시페닐)-5-[1-(1-헥사히드로아제피닐)-에틸]-1H-피롤, 2-[(2-아지비시클로[2.2.2]옥탄-2-일)메틸]-5-(3,5-디브로모-2-메톡시페닐)-1H-피롤, 2-[(9-아지비시클로[3.3.1]노난-9-일)메틸]-5-(3,5-디브로모-2-메톡시페닐)-1H-피롤, 2-(3,5-디브로모-2-메톡시페닐)-5-[1-(1-피페리디닐)프로필]-1H-피롤, 2-(N-시클로헥실메틸-N-에틸아미노메틸)-5-(3,5-디브로모-2-메톡시페닐)-1H-피롤, 2-[2-페닐-1-(1-피페리디닐)에틸]-5-(5-브로모-2,3-디메톡시페닐)-1H-피롤, 2-(5-에틸술포닐-2-메톡시페닐)-5-[1-(1-피페리디닐-에틸)-1H-피롤, 용출이 늦은 에난시오머와, 2-(5-에틸술포닐-2-메톡시페닐)-5-[1-(1-피페리디닐)-에틸)-1H-피롤, 용출이 빠른 에나시오머, 2-(5-에털술포닐-2-메톡시페닐)-5-(1-(1,2,3,6-테트라히드로피리디닐)메틸)-1H-피롤, 2-(5-에틸술포닐-2-메톡시페닐)-5-(1-(1-(1,2,3,6-테트라히드로피리디닐)에틸)-1H-피롤, 2-[(2-아자비시클로[3.2.1.]옥탄-2-일)메틸]-5-(5-에틸술포닐-2-메톡시페닐)-1H-피롤. 2-(5-에틸술포닐-2-메톡시페닐)-5-[1-(1-피롤리디닐)에틸]-1H-피롤, 2-(5-에틸술포닐-2-메톡시페닐)-5-[N-에틸-N-(2-티에[닐)메틸아미노메틸]-1H-피롤, 2-(5-에틸술포닐-2-메톡시페닐)-5[N-에틸-N-(2-푸릴)메틸아미노메틸]-1H-피롤, 2-(5-에틸술포닐-2-메톡시페닐)-5(N-벤질-N-프로필아미노메틸]-1H-피롤, 2-(3-브로모-5-에티술포닐-2-메톡시페닐)-5-[N-에틸-N-(4-메톡시페닐)메틸아미노메틸]-1H-피롤, 2-(5-에틸술포닐-2-메톡시페닐)-5-[N-에틸-N-(4-메톡시페닐)메틸아미노메틸]-1H-피롤, 2-(5-디메틸설파모일-2-메톡시페닐)-5-[1-(피페리디닐)메딜]-1H-피롤, 2-[(2-아자비시클로[2,2,1]헵탄-2-일)메틸]-5-(5-에틸술포닐-2-메톡시페닐)-1H-피롤, 2-[(2-아자비시클로[2.2.1]헵탄-2-일)메틸]-5 - (5 -에틸술포닐-2-메톡시페닐)-1H-피롤, 2-[(2-아자비시클로[2.2.1]헵탄-2-일)메틸]-5-(5-에틸술포닐-2-메톡시페닐)-1H-피롤, 2-[(2-아자비시클로[2.2.1]헵트-5-엔-2-일)메틸]-5-(5-에틸술포닐-2-메톡시페닐)-1H-피롤, 2-[(2-아자비시클로[3.2.1]옥트-6-엔-2-일)메틸]-5-(5-에틸술포닐-2-메톡시페닐)-1H-피롤, 2-(2-메톡시-5-메틸술포닐페닐)-5-(1-피페리디닐메틸)-1H-피롤, 2-(2,3-디메톡시-5-에틸술포닐페닐)-5-(1-피페리디닐메틸)-1H-피롤, 2-[(3-아자비시클로[3.2.1]옥탄-3-3-일)메틸]-5-(5-에틸술포닐-2-메톡시페닐)-1H-피롤, 2-(2-애틸-2-아자비시클로[2.2.1]헵탄-3-일)-5-(5-에틸술포닐-2-메톡시페닐)-1H-피롤, 2-[1-(2-아자비시클로[2.2.1]헵탄-2-일)에틸]-5-(5-에틸술포닐-2-메톡시페닐)-1H-피롤, 2-(5-에틸술포닐-2-메톡시페닐)-5-[N-에틸-N-(1-나프틸)메틸아미노메틸]-1H-피롤, 2-(5-이소프로필술포닐-2-메톨시페닐)-5-(1-피페리디닐메틸]-1H-피롤, (±) 트랜스-2-(5-에틸술포닐-2-메톡시페닐)-5-(퍼히드로이소퀴놀리닐메틸)-1H-피롤.
  8. (a) 포름알데히드 존재하에 하기 식(II)의 화합물을 아민 HNR8R9과 만니히 반응을 수행하여 Y가 -CH2NR8R9인 식(I)의 화합물을 제조하고, (b) 식(II)의 화합물을 식 R7C(O)NR8R9의 아미드 또는 그룹(b)의 2-옥소 유도체 각각과 빌즈마이어 반응을 수행시킨 다음 환원시켜 Y가 -CHR7NR8R9또는 식(b)의 그룹인 화합물을 제조하고, (c) 하기 식(Ⅲ)의 화합물을 아민 HNR8R9과 환원성 아민화를 수행하여 Y가 -CH2NR8R9인 화합물을 제조하고, 이어서 임의로 이들의 염을 형성하는 것으로 이루어지는 식(I)의 화합물을 제조하는 방법.
  9. 식(I)의 화합물 또는 생리적으로 허용 가능한 이들의 염의 유효량을 그것을 필요로 하는 개체에게 투여하는 것으로 이루어지는 도파민 D3수용체의 변형을 요하는 질환을 치료하는 방법.
  10. 제9항에 있어서, 도파민 길항제가 요구되는 방법.
  11. 제9항 또는 10항에 있어서, 질환이 정신질환인 방법.
  12. 도파민 D3수용체의 변형을 요하는 질환을 치료하기 위한 약제를 제조하기 위한 식(I)의 화합물 또는 생리적으로 허용 가능한 이들의 염의 용도.
  13. 식(I)의 화합물 또는 생리적으로 허용 가능한 이들의 염과 생리적으로 허용 가능한 담체로 이루어진 약제학적 조성물.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019950700431A 1992-08-06 1993-07-29 도파민 D₃수용체 길항제인 5-(2-옥시페닐)-피롤 유도체(5-(2-Oxyphenyl)-Pyrrole Derivatives as Dopamine D₃Receptor Antagonists) KR950702962A (ko)

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