KR930004268A - 벤조[f]퀴놀리논 - Google Patents

벤조[f]퀴놀리논 Download PDF

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KR930004268A
KR930004268A KR1019920014992A KR920014992A KR930004268A KR 930004268 A KR930004268 A KR 930004268A KR 1019920014992 A KR1019920014992 A KR 1019920014992A KR 920014992 A KR920014992 A KR 920014992A KR 930004268 A KR930004268 A KR 930004268A
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hydrogen
alkyl
methyl
amino
carbon
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에드먼드 오디아 제임스
스티븐 허쉬 켄네쓰
데이비드 존스 챨스
어니스트 로우혼 데이비드
아메스 맥퀘이드 로레타
오토 웨이겔 리랜드
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원본미기재
일라이 릴리 앤드 캄파니
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Abstract

내용 없음.

Description

벤조[f]퀴놀리논
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (14)

  1. 하기 일반식(Ⅰ)을 갖는 화합물 또는 그의 약학적으로 허용되는 염.
    상기식에서, R은 수소, C1-C4알킬, 비치환되거나 치환된 펜(C1-C4)알킬이고, Z 및 Z1은 독립적으로 수소 및 C1-C4알킬 중에서 선택되거나, 또는 Z 및 Z1중 하나는 R5와 함께 탄소-탄소 결합을 형성하고, Y는 수소 또는 메틸이거나, 또는 R1과 함께 탄소-탄소 결합을 형성하고, R1은 수소이거나, 또는 Y및 R3중 하나와 함께 탄소-탄소 결합을 형성하고, R2는 수소 또는 C1-C4알킬이고, R3는 수소이거나, 또는 R1과 함께 탄소-탄소 결합을 형성하고, R4는 수소이거나, 또는 R5와 함께 탄소-탄소 결합을 형성하고, R5는 수소이거나, 또는 Z 및 Z1중 하나와 함께 탄소-탄소 결합을 형성하고, n은 1 또는 2이고, X는 수소, 할로겐, NO2, 시아노, CF3, C1-C6알킬, C1-C6알콕시, 카복시, C1-C6알콕시카보닐, 아미노, C1-C4알킬아미노, C1-C4디알킬아미노, 아미도, C1-C4알킬아미도, C1-C4디알킬아미도, 머캅토, C1-C6알킬티오, C1-C6알킬설피닐, C1-C6알킬 설포닐 또는 -A-R6그룹(이때, A는 C1-C6알킬렌, C2-C6알케닐렌 또는 C2-C6알키닐렌이고, R6는 할로겐, 하이드록시, CF3, C1-C6알콕시, 카복시, C1-C6알콕시카보닐, 아미노, C1-C4알킬아미노, C1-C4디알킬아미노, 아미도, C1-C4알킬아미도, C1-C4디알킬아미도, C1-C4알킬설포닐아미노, 아미노설포닐 또는 C1-C4알킬아미노설포닐이다)이나, 단 (a) R1및 R5중 적어도 하나는 수소이고, (b) R이 수소, 메틸, 에틸 또는 벤질일 때, X는 수소 또는 메톡시가 아니고, (c) R이 메틸일 때, R2는 메틸이 아니다.
  2. 제1항에 있어서, 트랜스-dl-8-클로로-4-메틸-1,2,3,4,4a,5,6,10b-옥타하이드로벤조[f]퀴놀린-3-온 또는 그의 약학적으로 허용된 염인 화합물.
  3. 제1항에 있어서, 트랜스-dl-4,8-클로로-1,2,3,4,4a,5,6,10b-옥타하이드로벤조[f]퀴놀린-3-온 또는 그의 약학적으로 허용된 염인 화합물.
  4. 제1항에 있어서, 트랜스-dl-8-브로모-4-메틸-1,2,3,4,4a,5,6,10b-옥타하이드로벤조[f]퀴놀린-3-온 또는 그의 약학적으로 허용된 염인 화합물.
  5. 제1항에 있어서, (-)-(4aR)-(10bR)-8-클로로-4-메틸-1,2,3,4,4a,5,6,10b-옥타하이드로벤조[f]퀴놀린-3-온 또는 그의 약학적으로 허용된 염인 화합물.
  6. 제1항에 있어서, (+)-(4aS)-(10bS)-8-클로로-4-메틸-1,2,3,4,4a,5,6,10b-옥타하이드로벤조[f]퀴놀린-3-온 또는 그의 약학적으로 허용된 염인 화합물.
  7. 활성 성분으로서의 제1항 내지 제6항중 어느 한 항에 청구된 화합물을 그에 대한 하나 이상의 약학적으로 허용되는 담체, 희석제 또는 부형제와 함께 포함하는 5α-환원효소 억제 제제.
  8. 활성 성분으로서의 제1항 내지 제6항중 어느 한 항에 청구된 화합물을 그에 대한 하나 이상의 약학적으로 허용되는 담체, 희석제 또는 부형제와 함께 포함하는 양성 건립선 과형성, 남성형 대머리, 남성형 다모증 또는 전립선 암 치료 제제.
  9. 활성 성분으로서의 제1항 내지 제6항중 어느 한 항에 청구된 화합물을 그에 대한 하나 이상의 약학적으로 허용되는 담체, 희석제 또는 부형제와 함께 포함하는 안드로겐성 탈모증 또는 지루성 피부염 치료 제제.
  10. 하기 일반식(Ⅰ)을 갖는 화합물 또는 그의 약학적으로 허용되는 염을 안드로겐성 탈모증, 남성형 대머리 또는 남성형 다모증의 치료를 필요로 하는 성인에게 투여함을 포함하는, 성인에게서 상기 증상을 미용적으로 치료하는 방법.
    상기식에서, R은 수소, C1-C4알킬, 비치환되거나 치환된 펜(C1-C4)알킬이고, Z 및 Z1은 독립적으로 수소 및 C1-C4알킬 중에서 선택되거나, 또는 Z 및 Z1중 하나는 R5와 함께 탄소-탄소 결합을 형성하고, Y는 수소 또는 메틸이거나, 또는 R1과 함께 탄소-탄소 결합을 형성하고, R1은 수소이거나, 또는 Y및 R3중 하나와 함께 탄소-탄소 결합을 형성하고, R2는 수소 또는 C1-C4알킬이고, R3는 수소이거나, 또는 R1과 함께 탄소-탄소 결합을 형성하고, R4는 수소이거나, 또는 R5와 함께 탄소-탄소 결합을 형성하고, R5는 수소이거나, 또는 Z 및 Z1중 하나와 함께 탄소-탄소 결합을 형성하고, n은 1 또는 2이고, X는 수소, 할로겐, NO2, 시아노, CF3, C1-C6알킬, C1-C6알콕시, 카복시, C1-C6알콕시카보닐, 아미노, C1-C4알킬아미노, C1-C4디알킬아미노, 아미도, C1-C4알킬아미도, C1-C4디알킬아미도, 머캅토, C1-C6알킬티오, C1-C6알킬설피닐, C1-C6알킬 설포닐 또는 -A-R6그룹(이때, A는 C1-C6알킬렌, C2-C6알케닐렌 또는 C2-C6알키닐렌이고, R6는 할로겐, 하이드록시, CF3, C1-C6알콕시, 카복시, C1-C6알콕시카보닐, 아미노, C1-C4알킬아미노, C1-C4디알킬아미노, 아미도, C1-C4알킬아미도, C1-C4디알킬아미도, C1-C4알킬설포닐아미노, 아미노설포닐 또는 C1-C4알킬아미노설포닐이다)이나, 단 (a) R1및 R5중 적어도 하나는 수소이고, (b) R이 수소, 메틸, 에틸 또는 벤질일 때, X는 수소 또는 메톡시가 아니고, (c) R이 메틸일 때, R2는 메틸이 아니다.
  11. 하기 일반식(Ⅱ)의 화합물 또는 그의 약학적으로 허용되는 염.
    상기식에서, X는 수소, 할로겐, NO2, 시아노, CF3, C1-C6알킬, C1-C6알콕시, 카복시, C1-C6알콕시카보닐, 아미노, C1-C4알킬아미노, C1-C4디알킬아미노, 아미도, C1-C4알킬아미도, C1-C4디알킬아미도, 머캅토, C1-C6알킬티오, C1-C6알킬설피닐, C1-C6알킬 설포닐 또는 -A-R6그룹(이때, A는 C1-C6알킬렌, C2-C6알케닐렌 또는 C2-C6알키닐렌이고, R6는 할로겐, 하이드록시, CF3, C1-C6알콕시, 카복시, C1-C6알콕시카보닐, 아미노, C1-C4알킬아미노, C1-C4디알킬아미노, 아미도, C1-C4알킬아미도, C1-C4디알킬아미도, C1-C4알킬설포닐아미노, 아미노설포닐 또는 C2-C4알킬아미노설포닐이다)이고, n은 1 또는 2이다.
  12. a) 1-메틸-2-테트랄론을 광학적으로 활성인 아민과 반응시켜 상응하는 1-메틸렌아민을 수득하고, b) 상기 1-메틸렌아민을 α, β-불포화 카보닐 화합물과 반응시켜 상응하는 메타노벤조사이클로옥탄-4-온을 수득하고, c) 상기 메타노벤조사이클로옥탄-4-온을 알콕시화 알칼리 금속과 반응시켜 상응하는 2,3,4,4a,9,10-헥사하이드로-4a-메틸, 페난트렌-2-온을 수득하고, d) 상기 페난트렌-2-온을 산화적으로 분해시켜 상응하는 3-[1-메틸-1-(2-케토-1,2,3,4-테트라하이드로나프릴)]프로피온산을 수득하고, e) 상기 프로피온산을 암모니아 또는 1급 아민과 반응시켜 상응하는 10b-메틸-1,2,3,4,6,10b-헥사하이드로벤조[f]퀴놀린-3-온을 수득하고, f) 상기 헥사하이드로벤조[f]퀴놀린-3-온을 환원시켜 상응하는 하기 일반식의 옥타하이드로 벤조[f]퀴놀린-3-온을 수득함을 포함하여, 하기 일반식을 갖는 화합물 또는 그의 약학적으로 허용되는 염을 제조하는 방법.
    상기식에서, R은 수소, C1-C4알킬, 비치환되거나 치환된 펜(C1-C4)알킬이고, Z 및 Z1은 독립적으로 수소 및 C1-C4알킬 중에서 선택되고, Y는 수소 또는 메틸이고, R2는 수소 또는 C1-C4알킬이고, n은 1 또는 2이고, X는 수소, 할로겐, NO2, 시아노, CF3, C1-C6알킬, C1-C6알콕시, 카복시, C1-C6알콕시카보닐, 아미노, C1-C4알킬아미노, C1-C4디알킬아미노, 아미도, C1-C4알킬아미도, C1-C4디알킬아미도, 머캅토, C1-C6알킬티오, C1-C6알킬설피닐, C1-C6알킬 설포닐 또는 -A-R6그룹(이때, A는 C1-C6알킬렌, C2-C6알케닐렌 또는 C2-C6알키닐렌이고, R6는 할로겐, 하이드록시, CF3, C1-C6알콕시, 카복시, C1-C6알콕시카보닐, 아미노, C1-C4알킬아미노, C1-C4디알킬아미노, 아미도, C1-C4알킬아미도, C1-C4디알킬아미도, C1-C4알킬설포닐아미노, 아미노설포닐 또는 C1-C4알킬아미노설포닐이다)이다.
  13. (a) 하기 일반식(Ⅰ) 화합물의 라세미체의 메탄올 용액을 강산과 접촉시켜 1-(2-메톡시카보닐에틸)-2-(아미노)-1,2,3,4-테트라 하이드로나프탈렌을 수득하는 단계, (b) 상기 단계(a)에서 수득한 테트라하이드로나프탈렌을 광학적으로 활성인 디-p-톨루오일타르타르산과 접촉시켜 상응하는 테트라하이드로나프탈렌 염을 수득하는 단계, 및 (c) 상기 단계(b)에서 수득한 염을 염기로 처리하여 실질적으로 한가지의 광학적으로 활성인 이성체를 수득하는 단계를 필수적으로 포함하는, 하기 일반식(Ⅰ)을 갖는 화합물의 라세미체를 그의 광학 이성체 성분으로 분할하는 방법.
    상기식에서, R은 수소, C1-C4알킬이고, Z 및 Z1은 독립적으로 수소 및 C1-C4알킬 중에서 선택되고, Y는 수소이며, R1, R2, R3, R4및 R5는 모두 수소이고, n은 1 또는 2이고, X는 수소, 할로겐, NO2, CF3, C1-C6알킬, C1-C4알콕시, 아미노, C1-C4알킬아미노, C1-C4디알킬아미노, 머캅토, 또는 C1-C6알킬티오이다.
  14. 디-p-톨루오일-(D) 또는 (L)-타르타르산과 하기 일반식을 갖는 화합물의 트랜스 이성체와의 염.
    상기식에서, R은 수소, C1-C4알킬이고, Z 및 Z1은 독립적으로 수소 및 C1-C4알킬 중에서 선택되고, n은 1 또는 2이고, X는 수소, 할로겐, NO2, CF3, C1-C6알킬, C1-C4알콕시, 아미노, C1-C4알킬아미노, C1-C4디알킬아미노, 머캅토, 또는 C1-C6알킬티오이다.
    ※참고사항:최초출원 내용에 의하여 공개하는 것임.
KR1019920014992A 1991-08-21 1992-08-20 벤조(에프)퀴놀리논 KR100235562B1 (ko)

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