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KR970001344A - α-아드레날린수용체 길항물질로서의 피리미딘디온, 피리미딘트리온, 트리아진디온, 테트라히드로퀴나졸린디온 유도체 - Google Patents

α-아드레날린수용체 길항물질로서의 피리미딘디온, 피리미딘트리온, 트리아진디온, 테트라히드로퀴나졸린디온 유도체 Download PDF

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KR970001344A
KR970001344A KR1019960020447A KR19960020447A KR970001344A KR 970001344 A KR970001344 A KR 970001344A KR 1019960020447 A KR1019960020447 A KR 1019960020447A KR 19960020447 A KR19960020447 A KR 19960020447A KR 970001344 A KR970001344 A KR 970001344A
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alkyl
hydro
aryl
compound
methyl
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KR100446877B1 (ko
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더블유. 밴틀 개리
구즈만 엥겔
제이. 로페즈-타피아 프라시스코
페레즈-메드라노 아르투로
비. 쇼그렌 에릭
알. 엘워디 토드
제이미-피구에로아 사울
제이. 모간즈 쥬니어 데이비드
알. 피스터 쥐르그
엑스. 탈라마스 프랑시스코
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프리돌린 클라우스너·롤란드 보러
에프. 호프만-라 롯슈 아크티엔게젤샤프트
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Abstract

본 발명은 하기 일반식(Ⅰ)의 신규한 α1-아드레날린수용체 길항물질, 및 그의 제약학상 허용되는 염 및 N-옥사이드에 관한 것이다;
(I)
상기 식 중, R1은 아세틸아미노, 아미노, 시아노, 트리플루오로아세틸아미노, 할로, 히드로, 히드록시, 니트로, 메틸술포닐아미노, 2-프로피닐옥시, 임의로 1내지 3개의 할로 원자로 추가로 치환될 수 있는, (C1-6)알킬, (C3-6)시클로알킬, (C3-6)시클로알킬(C1-4)알킬, (C1-6)알킬옥시, (C3-6)시클로알킬옥시, (C3-6)시클로알킬, (C1-4)알킬옥시 및 (C1-4)알킬티오로부터 선택되는기, 또는 아릴, 아릴(C1-4)알킬, 헤테로아릴, 헤테로아릴(C1-4)알킬, 아릴옥시, 아릴(C1-4)알킬옥시 헤테로아릴옥시 및 헤테로아릴(C1-4)알킬옥시로부터 선택되는기(여기서 아릴 및 헤테로아릴은 임의로 할로 및 시아노로부터 독립적으로 선택되는 1 내지 2개의 라디칼로 추가로 치환될 수 있음)이고; R2는 시아노, 할로 , 히드로 히드록시 또는 임의로 1 내지 3개의 할로겐 원자로 추가로 치환될 수 있는, (C1-6)알킬 및 (C1-6)알킬옥시로부터 선택되는 기이고 ; R3및 R4는 모두 히드로 또는 메틸이거나, 또는 함께 에틸렌이고; R5는 일반식
로부터 선택되는 기이고; X는 C(0), CH2또는 CH(OH)이고; Y는 CH2또는 CH(OH)이고; Z는N 또는 C(R9)(여기서, R9는 히드로, (C1-6)알킬 또는 히드록시임)이고; R6은 히드로, 임의로 1내지 3개의 할로 원자로 추가로 치환될 수 있는, (C1-6)알킬, (C3-6)시클로알킬, (C3-6)시클로알킬(C1-6)알킬로부터 선택되는 기이거나, 또는 아릴, 헤테로아릴, 아릴(C1-4)알킬 및 헤테로아릴 (C1-4)알킬로부터 선택되는 기(여기서 아릴 및 헤테로아릴은 임의로 치환, 시아노, (C1-6)알킬옥시, (C1-6)알킬 및 아릴로부터 선택되는 1내지 3개의 라디탈로 추가로 치환될 수 있음)이고; R7은 (C1-6)알카노일, 카르바모일, 시아노, 디(C1-6)알킬아미노, 할로, 히드로, 히드록시, 히드록시이미노메틸, (C1-6)알킬술포닐, (C1-4)알킬티오, 임의로 할로, 히드록시 또는 (C1-6)알킬옥시로부터 선택되는 1내지 3개의 라디칼로 추가로 치환될 수 있는, (C1-6)알킬, (C3-6)시클로알킬, (C1-6)알킬옥시 및 (C1-6)알킬옥시 (C1-4)알킬로부터 선택되는 기, 또는 아릴, 헤테로아릴, 아릴(C1-4)알킬 및 헤테로아릴(C1-4) 알킬로부터 선택되는 기(여기서 아릴 및 헤테로아릴은 임의로 할로, 시아노, (C1-6)알킬옥시, (C1-6)알킬 및 아릴로부터 선택된는 1 내지 3개의 라디칼로 추가로 치환될 수 있음)이거나 또는 R7및 R9가 함께 테트라메틸렌이며; R8은 각각 독립적으로 히드로, 히드록시, 메틸 또는 에틸이다.

Description

아드레날린수용체 길항물질로서의 피리미딘디온, 피리미딘트리온, 트리아진디온, 테트라히드로퀴나졸린디온 유도체
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Claims (22)

  1. 하기 일반식(Ⅰ)의 화합물, 및 그의 제약학상 허용되는 염 및 N-옥사이드:
    (I)
    상기 식 중, R1은 아세틸아미노, 아미노, 시아노, 트리플루오로아세틸아미노, 할로, 히드로, 히드록시, 니트로, 메틸술포닐아미노, 2-프로피닐옥시, 임의로 1내지 3개의 할로 원자로 추가로 치환될 수 있는, (C1-6)알킬, (C3-6)시클로알킬, (C3-6)시클로알킬(C1-4)알킬, (C1-6)알킬옥시,(C3-6)시클로알킬옥시, (C3-6)시클로알킬, (C1-4)알킬옥시 및 (C1-4)알킬티오로부터 선택되는기, 또는 아릴, 아릴(C1-4)알킬, 헤테로아릴, 헤테로아릴(C1-4)알킬, 아릴옥시, 아릴(C1-4)알킬옥시 헤테로아릴옥시 및 헤테로아릴(C1-4)알킬옥시로부터 선택되는기(여기서 아릴 및 헤테로아릴은 임의로 할로 및 시아노로부터 독립적으로 선택되는 1 내지 2개의 라디칼로 추가로 치환될 수 있음)이고; R2는 시아노, 할로 , 히드로, 히드록시 또는 임의로 1 내지 3개의 할로겐 원자로 추가로 치환될 수 있는, (C1-6)알킬 및 (C1-6)알킬옥시로부터 선택되는 기이고 ; R3및 R4는 모두 히드로 또는 메틸이거나, 또는 함께 에틸렌이고; R5는 일반식
    로부터 선택되는 기이고; X는 C(0), CH2또는 CH(OH)이고; Y는 CH2또는 CH(OH)이고; Z는N 또는 C(R9)(여기서, R9는 히드로, (C1-6)알킬 또는 히드록시임)이고; R6은 히드로, 임의로 1내지 3개의 할로 원자로 추가로 치환될 수 있는, (C1-6)알킬, (C3-6)시클로알킬, (C3-6)시클로알킬(C1-4)알킬로부터 선택되는 기이거나, 또는 아릴, 헤테로아릴, 아릴(C1-4)알킬 및 헤테로아릴 (C1-4)알킬로부터 선택되는 기(여기서 아릴 및 헤테로아릴은 임의로 치환, 시아노, (C1-6)알킬옥시, (C1-6)알킬 및 아릴로부터 선택되는 1내지 3개의 라디탈로 추가로 치환될 수 있음)이고; R7은 (C1-6)알카노일, 카르바모일, 시아노, 디(C1-6)알킬아미노, 할로, 히드로, 히드록시, 히드록시이미노메틸, (C1-6)알킬술포닐, (C1-4)알킬티오, 임의로 할로, 히드록시 또는 (C1-6)알킬옥시로부터 선택되는 1내지 3개의 라디칼로 추가로 치환될 수 있는, (C1-6)알킬, (C3-6)시클로알킬, (C1-6)알킬옥시 및 (C1-6)알킬옥시 (C1-4)알킬로부터 선택되는 기, 또는 아릴, 헤테로아릴, 아릴(C1-4)알킬 및 헤테로아릴(C1-4) 알킬로부터 선택되는 기(여기서 아릴 및 헤테로아릴은 임의로 할로, 시아노, (C1-6)알킬옥시, (C1-6)알킬 및 아릴로부터 선택되는 1 내지 3개의 라디칼로 추가로 치환될 수 있음)이거나 또는 R7및 R9가 함께 테트라메틸렌이며; R8은 각각 독립적으로 히드로, 히드록시, 메틸 또는 에틸이다.
  2. 제1항에 있어서, R1이 임의로 1 내지 3개의 불소 원자로 추가로 치환될 수 있는 (C1-6)알킬옥시, 또는 헤테로아릴이고; R2가 히드로, 할로, 히드록시 또는 (C1-6)알킬이고; R5가 일반식(a), (b) 및 (c)로부터 선택되는 기이고, 이때 R6이 히드로, (C1-6)알킬, (C3-6)시클로알킬(C1-4)알킬, 헤테로아릴(C1-4)알킬, 또는 임의로 할로, (C1-6)알킬옥시, (C1-6)알킬 및 아릴로부터 선택되는 1 내지 3개의 라디칼로 추가로 치환될 수 있는, 벤질 및 페닐로부터 선택되는 기이고, R7이 카르바모일, 시아노, 할로, 히드로, 히드록시이미노메틸, 히드록시메틸, 또는 알킬기가 임의로 1 내지 3개의 불소 원자로 추가로 치환될 수 있는 (C1-6)알킬이거나, 또는 R7및 R9가 함께 테트라메틸렌인 화합물.
  3. 제2항에 있어서, R1이 메톡시, 에톡시, 2,2,2-트리플루오로에톡시, 옥사졸릴 또는 피롤릴이고; R2가 히드로, 클로로, 플루오로, 히드록시 또는 메틸이고; R6이 히드로, 메틸 시클로헥실메틸, 피리딜메틸, 피라지닐메틸, 푸릴메틸, 티에닐메틸, 비페닐메틸, 또는 임의로 클로로, 플루오로, 메틸 또는 메톡시로부터 선택되는 1 내지 3개의 라디칼로 추가로 치환될 수 있는, 벤질 및 페닐로부터 선택된 기이고; R7이 카르바모일, 시아노, 할로, 히드로, 히드록시이미노메틸, 히드록시메틸, 메틸 에틸, 프로필, 트리플루오로메틸이거나, 또는 R7및 R9가 함께 테트라메틸렌이고; X가 CH2이고 R8라디칼이 각각 히드로이거나, 또는 X가 CH(OH)이고 R8라디칼 중의 1개가 히드록시인 화합물.
  4. 제3항에 있어서, R1이 2,2,2-트리플루오로에톡시이고; R3및 R4가 각각 히드로이고; R5가 일반식(a)의 기(이때, R7은 히드로, 히드록시메틸 또는 메틸이고, Z는 C(R9)이고, R9는 히드로 또는 메틸 메틸임)이거나, 또는 일반식(c)의 기 (이때, X는 CH(OH)이고 R8라디칼 중의 1개는 히드록시이고 나머지는 메틸임)인 화합물.
  5. 제4항에 있어서, R1이 2,2,2-트리플루오로에톡시이고, Z가 CH이고, R2가 히드로이고, R6이 히드로이고, R7이 메틸인, 즉,3-(3-{4-[2-(2,2,2-트리플루오로에톡시)페닐]피레라진-1-일}프로필)-5-메틸-2,4(1H,3H)-피리미딘디온인 화합물 및 그의 제약학상 허용되는 염.
  6. 제5항에 있어서, 3-(3-{4-[2-(2,2,2-트리플루오로에톡시)페닐]피레라진-1-일}프로필)-5-메틸-2,4(1H,3H)-피리미딘디온 염산염인 화합물.
  7. 제4항에 있어서, R1이 2,2,2-트리플루오로에톡시이고, Z가 CH이고, R2가 4-위치의 플루오로이고, R6이 히드로이고, R7이 메틸인, 즉, 3-(3-{4-[4-플루오로-2--(2,2,2-트리플루오로에톡시)페닐]피페라진-1-일}프로필)--5-메틸-2,4(1H,3H)-피리미딘디온인 화합물 및 그의 제약학상 허용되는 염.
  8. 제7항에 있어서, 3-(3-{4-[4-플루오로-2--(2,2,2-트리플루오로에톡시)페닐]피페라진-1-일}프로필)--5-메틸-2,4(1H,3H)-피리미딘디온 푸마레이트인 화합물.
  9. 제4항에 있어서 R1이 2,2,2-트리플루오로에톡시이고, Z가 CH이고, R2가 4-위치의 플루오로이고, R6이 히드로이고, R7이 에틸인, 즉, 3-(3-{4-[4-플루오로-2--(2,2,2-트리플루오로에톡시)페닐]피페라진-1-일}프로필)-5-에틸-2,4(1H,3H)-피리미딘디온인 화합물 및 그의 제약학상 허용되는 염.
  10. 제9항에 있어서, 3-(3-{4-[4-플루오로-2-(2,2,2-트리플루오로에톡시)페닐]피페라진-1-일}프로필)-5-에틸-2,4(1H,3H)-피리미딘디온 염산염인 화합물.
  11. 제4항에 있어서, R1이 옥사졸-2-일이고, Z가 CH이고, R2가 4-위치의 플루오로이고, R6이 히드로이고, R7이 메틸인, 즉, 3-(3-{4-[4-플루오로-2-옥사졸-2-일페닐)피페라진-1-일]프로필}--5-메틸-2,4(1H,3H)-피리미딘디온인 화합물 및 그의 제약학상 허용되는 염.
  12. 제11항에 있어서, 3-(3-{4-[4-플루오로-2-옥사졸-2-일페닐)피페라진-1-일]프로필}--5-메틸-2,4(1H,3H)-피리미딘디온 옥살레이트인 화합물.
  13. 제4항에 있어서, R1이 2,2,2-트리플루오로에톡시이고, Z가 CH이고, R2가 4-위치의 플루오로이고, R6이 히드로이고, R7이 히드록시메틸인, 즉, 3-(3-{4-[4-플루오로-2--(2,2,2-트리플루오로에톡시)페닐]피페라진-1-일}프로필)-5-히드록시메틸-2,4(1H,3H)-피리미딘디온인 화합물 및 그의 제약학상 허용되는 염.
  14. 제13항에 있어서, 3-(3-{4-[4-플루오로-2--(2,2,2-트리플루오로에톡시)페닐]피페라진-1-일}프로필)-5-히드록시메틸-2,4(1H,3H)-피리미딘디온푸마레이트인 화합물.
  15. 제4항에 있어서, 제4항에 있어서, R1이 2,2,2-트리플루오로에톡시이고, R2가 4-위치의 플루오로이고; R3및 R4가 각각 히드로이고; R5가 일반식(c)의 기이고, 이때 X가 CH(OH)이고 R8라디칼 중의 1개가 히드록시이고 나머지는 메틸인, 즉, 시스-3-(3-{4-[4-플루오로--2-(2,2,2-트리플루오로에톡시)페닐]피페라진-1-일}프로필)-5,6-디히드록시-5-메틸-5,6-디히드로-2,4(1H,3H)-피리미딘디온인 화합물 및 그의 제약학상 허용되는 염.
  16. 제15항에 있어서, 시스-3-(3-{4-[4-플루오로--2-(2,2,2-트리플루오로에톡시)페닐]피페라진-1-일}프로필)-5,6-디히드록시-5-메틸-5,6-디히드로-2,4(1H,3H)-피리미딘디온 푸마레이트의(+)-거울상이성질체인 화합물.
  17. 제15항에 있어서, 시스-3-(3-{4-[4-플루오로--2-(2,2,2-트리플루오로에톡시)페닐]피페라진-1-일}프로필)-5,6-디히드록시-5-메틸-5,6-디히드로-2,4(1H,3H)-피리미딘디온 푸마레이트의(-)-거울상이성질체인 화합물.
  18. 치료 유효량의 제1항 내지 제17항 중 어느 한 항에 따른 화합물 및 제약학상 허용되는 부형제를 포함하는 약학 조성물.
  19. (a) 하기 일반식 3의 화합물 또는 그의 보호된 유도체를 하기 일반식 2의 화합물 또는 그의 보호된 유도체로 알킬화시킨 다음 필요에 따라 보호기제거하는 단계; 또는 (b) 식 H-R5의 화합물을 하기 일반식 5의 화합물로 알킬화시키는 단계; 및 (c)임의로 R6이 벤질인 일반식 Ⅰ의 화합물을 추가로 탈벤질화시켜 R6이 히드로인 일반식 Ⅰ의 화합물을 얻는 단계; (d) 임의로 R6이 히드로인 일반식 Ⅰ의 화합물을 추가로 알칼화시켜 R6이 (C1-6)알킬, (C3-6)시클로알킬, (C3-6)시클로알킬 (C1-4)알킬, 또는 아릴, 헤테로아릴, 아릴 (C1-4)알킬 및 헤테로아릴 (C1-4)알킬로부터 선택되는 기 (여기서 아릴 및 헤테로아릴은 임의로 할로, 시아노, (C1-6)알킬옥시, (C1-6)알킬 및 아릴로부터 선택되는 1 내지 3개의 라디칼로 추가로 치환될 수 있음)인 일반식 Ⅰ의 화합물을 얻는 단계; (e) 임의로 일반식 Ⅰ의 화합물을 추가로 산화시켜 N-옥사이드 유도체를 얻는 단계; (f) 임의로 일반식Ⅰ의 화합물의 N-옥사이드 유도체를 산화되지 않은 형태로 추가로 환원시키는 단계; (g) 임의로 일반식 Ⅰ의 화합물을 제약학상 허용되는 염으로 추가로 전환시키는 단계; 및 (h) 임의로 일반식 I의 화합물의 염 형태를 비염 형태로 추가로 전환시키는 단계를 포함하는, 하기 일반식(Ⅰ)의 화합물 및 그의 제약학상 허용되는 염 및 N-옥사이드의 제조 방법;
    상기 식 중, R1. R2. R3. R4및 R5는 각각 제1항에 정의한 바와 같고, L은 이탈기이다.
  20. 제19항에 따른 방법에 따라서 또는 그의 명백한 화학적 등가물에 의해 제조된 제1항 내지 제17항 중 어느 한 항에 따른 화합물.
  21. 약학활성있는 물질, 특히 양성 전립선 과형성증에 기인한 하부 요로의 폐쇄와 직간접적으로 관계있는 질병을 치료하기 위한 물질인 제1항 내지 제17항 중 어느 한 항에 따른 화합물.
  22. 약제, 특히 양성 전립선 과형성증에 기인한 하부 요로의 폐쇄와 직간접적으로 관계있는 질병을 치료하기 위한 약제의 제조에 사용되는, 제11항 내지 제17항 중 어느 한 항에 따른 화합물의 용도.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019960020447A 1995-06-09 1996-06-08 알파1아드레날린수용체길항물질로서의피리미딘디온,피리미딘트리온,트리아진디온,테트라히드로퀴나졸린디온유도체 Expired - Fee Related KR100446877B1 (ko)

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ES2157366T3 (es) 2001-08-16
CA2178548A1 (en) 1996-12-10
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MA23899A1 (fr) 1996-12-31
CZ290004B6 (cs) 2002-05-15
PE46497A1 (es) 1997-12-04
HK1013065A1 (en) 1999-08-13
CO4700472A1 (es) 1998-12-29
CN1149051A (zh) 1997-05-07
ZA964561B (en) 1996-12-09
HUP9601529A2 (hu) 1998-09-28
PT748800E (pt) 2001-10-30
EP0748800A2 (en) 1996-12-18
JP2721147B2 (ja) 1998-03-04
NO962412D0 (no) 1996-06-07
HU9601529D0 (en) 1996-07-29
CN1118459C (zh) 2003-08-20
EP0748800B1 (en) 2001-05-09
CZ169696A3 (en) 1997-01-15
IL118519A0 (en) 1996-09-12
ATE201016T1 (de) 2001-05-15
SG45486A1 (en) 1998-01-16
HUP9601529A3 (en) 2000-02-28
UY24257A1 (es) 2000-12-29
HU223594B1 (hu) 2004-09-28
TR970073A2 (tr) 1997-02-21
TW340846B (en) 1998-09-21
NO309424B1 (no) 2001-01-29
AR003428A1 (es) 1998-08-05
SA96170263B1 (ar) 2006-05-23
DE69612698D1 (de) 2001-06-13
BR9602705A (pt) 1998-09-08
DK0748800T3 (da) 2001-08-27
NZ286720A (en) 1998-08-26
DE69612698T2 (de) 2001-12-06
GR3036307T3 (en) 2001-10-31
PL188061B1 (pl) 2004-12-31
IL118519A (en) 1999-12-22
NO962412L (no) 1996-12-10
AU5469096A (en) 1996-12-19
EP0748800A3 (en) 1996-12-27
JPH09100269A (ja) 1997-04-15
AU710754B2 (en) 1999-09-30
KR100446877B1 (ko) 2004-11-06
PL314635A1 (en) 1996-12-23

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