KR890009871A - 티오포름아미드 유도체, 이를 포함하는 조성물 및 그 제조 방법 - Google Patents

티오포름아미드 유도체, 이를 포함하는 조성물 및 그 제조 방법 Download PDF

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KR890009871A
KR890009871A KR1019880016914A KR880016914A KR890009871A KR 890009871 A KR890009871 A KR 890009871A KR 1019880016914 A KR1019880016914 A KR 1019880016914A KR 880016914 A KR880016914 A KR 880016914A KR 890009871 A KR890009871 A KR 890009871A
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methyl
cyclohexanecarbothioamide
pyridyl
quinolinyl
group
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차알즈 쿡 데이비드
윌리엄 하트 테렌스
맥팔레인 머클레이 아이안
노어먼 펠프 레이먼 맬콤
존 애치슨 월시 로저
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테리 피이터 밀러
메이 앤드 베이커 리미팃드
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Publication of KR890009871A publication Critical patent/KR890009871A/ko

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Abstract

내용 없음

Description

티오포름아미드 유도체, 이를 포함하는 조성물 및 그 제조 방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (11)

  1. 하기 일반식(Ⅰ)의 티오포름아미드 유도체 및 제약학적으로 허용가능한 그 염;
    상기식에서 R은 1-4개의 탄소 원자를 함유하는 직쇄 또는 측쇄 알킬 라디칼을 나타내고, Het는 피리드-3-일, 이소퀴놀린-4-일, 테트라히드로퀴놀린-3-일, 퀴놀린-3-일, 피리다진-4-일, 피니미드-5-일, 티아졸-5-일, 티에노[2,3-b]피리딘-5-일, 피라진-2-일, 인돌-5-일, 및 티에노[3,2-b]피리딘-6일로 부터 선택되는 하나 또는 두개의 질소 원자를 함유하는 방향족 헤테로시클릭 라디칼(할로겐 원자 또는 1-개의 탄소 원자를 함유하는 직쇄 또는 측쇄 알킬 또는 알콕시 라디칼에 의해 임의로 치환됨)을 나타내고, Y는 에틸렌 또는 메틸렌 라디칼, 또는 원자가 결합을 나타내고, X는 카르보닐 또는 히드록시메틸렌기 또는 일반식 〉C=NOR1, 〉C=NN(R1)2또는 〉C=NN(R1)CON(R1)2(여기서 R1은 같거나 다를수 있으며, 각각 수소 원자 또는 C2-4-알케닐, 카르복시, C2-5-알콕시카르보닐, 히드록시, C1-4-알콕시, 카르바모일(하나 또는 두개의 C1-4알킬 기로 치환되거나 비치환됨) 아미노, C1-4-알킬아미노 및 디-C1-4-알킬아미노 기로 부터 선택된 하나 또는 그이상의 치환체에 의해 치환되거나 비치환된 1-4개의 탄소원자를 함유하는 직쇄 또는 측쇄 알킬 아디칼을 나타내거나, 벤질, 페네틸, 1-나프틸메틸, 2-나프틸메틸, 또는 피리드-3-일메틸 라디칼을 나타내며, 이들 각각은 고리상에서 하나 또는 그 이상의 할로겐 원자 또는 히드록시, C1-4-알킬, C1-4-알콕시(알콕시는 R1으로 표시된 알킬 기에 대해 정의된 바와 같이 치환되거나 비치환됨) 시아노, 니트로, 트리플루오로메틸, 카르복시, C1-4-알킬아미노, C2-5-알카노아미노 또는 C2-5-알코시카르보닐 기로 치환될 수 있거나 같은 질소 원자상의 두 R1치환체는 R1으로 표시된 알킬 라디칼에 대해 정의된 바와 같이 치환되거나 비치환된 사슬내 4-6개의 탄소 원자를 함유하는 직쇄 또는 측쇄 알킬렌 라디칼을 함께 형성시킬 수 있다).
  2. 제1항에 있어서, Y가 메틸렌 라디칼 또는 원자가 결합을 나타내는 화합물.
  3. 제1항 내지 제2항에 있어서, X가 R1이 제1항에서 정의된 바와 같은 일반식 〉C=NOR1의 기 또는 카르보닐 기를 나타내는 화합물.
  4. 제1항 내지 제3항 중 어느 한 항에 있어서, R1이 제1항에서 정의된 바와 같이 치환되거나 비치환된 1-4개의 탄소원WK를 함유하는 직쇄 또는 측쇄 알킬 라디칼을 나타내거나, 벤질, 피네틸, 1-나프틸메틸, 2-나프틸메틸 또는 피리드-3-일-메틸 라디칼(각각은 제1항에서 정의된 바와 같이 고라상에서 치환될 수 있다)을 나태내는 화합물.
  5. 제1항 내지 제4항 중 어느 한 항에 있어서, Het가 3-피리딜, 클로로피리드-3일, 5-브로모피리드-3-일, 3-퀴놀리닐, 4-이소퀴놀닐 또는 5-피리미딜을 나타내는화합물.
  6. 제1항, 제2항, 제4항 및 제5항 중 어느 한 항에 있어서, 하기 일반식(Ⅱ)의화합물:
    상기식에서 R, Het 및 Y는 히드록시 기가 -CSNHR 기에 대해 트랜스 위치에 있는 제1항 내지 제5항 중 어느 한항에 있어서 정의된 바와 같다.
  7. 제1항에 있어서,
    A (±)-N-메틸-2-옥소-1-(3-피리딜)시클로헥산-카르보티오아미드
    B (±)-N-메틸-2-옥소-1-(3-퀴놀리닐)-시클로헥산카르보티오아미드
    C (±)-N-메틸-2-옥소-1-(3-피리딜)시클로헵탄-카르보티오아미드
    D (±)-트랜스-N-메틸-2-히드록시-1-(3-피리딜)-시클로헥산카르보티오아미드
    E (±)-시스-N-메틸-2-히드록시-1-(3-피리딜)-시클로헥산카르보티오아미드
    F (±)-안티-N-메틸-2-히드록시미노-1-(3-피리딜)-시클로헥산카르보티오아미드
    G (±)-안티-N-메틸-2-메톡시이미노-1-(3-피리딜)-시클로헥산카르보티오아미드
    H (±)-안티-N-메틸-2-벤질옥시이미노-1-(3-피리딜)-시클로헥산크르보티오아미노
    I (±)-안티-N-메틸-2-히드록시이미노-1-(3-퀴놀리닐)-시클로헥산크로보티오아미드
    J (2S)-안티-2-(메톡시메틸)-1-[2'-(3-퀴놀리닐)-2'-메틸티오카르바모일 시클로헥실리덴아미노]피놀리딘
    K (2S)-안티-2-(메톡시메틸)-1-[2'-(3-피리딜)-2'-메틸티오카르바모일 시클로헥실리덴아미노]피놀리딘
    L (±)-안티-N-메틸-2-(2-디메틸아미노에톡시이미노)-1-(3-피리딜)시클로헥산카르보티오아미드
    M (±)-안티-N-메틸-2-(2-아미노에톡시이미노)-1-(3-피리딜)시클로헥산카르보티오아미드
    N (±)-안티-N-메틸-2-메톡시카르보닐메톡시이미노)-1-(3-피리딜)시클로헥산카르보티오아미드
    O (±)-안티-N-메틸-2-카르바모일메톡시이미노)-1-(3-피리딜)시클로헥산카르보티오아미드
    P (±)-안티-N-메틸-2-(2,3-디히드록싶로폭시이미노)-1-(3-피리딜)시클로헥산카르보티오아미드
    Q (±)-안티-N-메틸-2-(2-히드록시에톡시이미노)-1-(3-피리딜)시클로헥산카르보티오아미드
    R (±)-N-메틸-2-옥소-1-(6-클로로피리드-3-일)-시클로헥산카르보티오아미드
    S (±)-N-메틸-2-옥소-1-(5-브로모피리드-3-일)-시클로헥산카르보티오아미드
    T (±)-N-메틸-2-옥소-1-(3-피리딜)-시클로헥산-카르보티오아미드
    U (±)-N-메틸-2-옥소-1-(3-퀴놀리닐)-시클로헥산카르보티오아미드
    V (±)-안티-N-메틸-2-디메틸히드라조노-1-(3-퀴놀리닐)-시클로헥산카르보티오아미드
    W (±)-안티-N-메틸-2-디메틸히드라조노-1-(3-퀴놀리닐)-시클로헥산카르보티오아미드
    X (±)-안티-N-메틸-2-벤질옥시이미도-1-(3-퀴놀리닐)-시클로헥산카르보티오아미드
    Y (±)-안티-N-메틸-2-메톡시이미노-1-(3-퀴놀리닐)-시클로헥산카르보티오아미드
    Z (±)-안티-N-메틸-2-에톡시이미노-1-(3-퀴놀리딘)-시클로헥산카르보티오마미드
    AA (±)-안티-N-메틸-2-브톡시이미노-1-(3-퀴놀리닐)-시클로헥산카르보티오아미드
    AB (±)-안티-N-메틸-2-(3-이소프로필아미노-2-히드록시-프로폴시이미노)-1-(3-퀴놀리닐)시클로헥산-카르보티오아미드
    AC (±)-안티-N-메틸-2-삼차(t.)부톡시이미노-1-(3-퀴놀리닐)-시클로헥산카르보티오아미드
    AD (±)-안티-N-메틸-2-프로프-2-에톡시이미노-1-(3-퀴놀리닐)시클로헥산카르보티오아미드
    AE (±)-안티-N-메틸-2-나프트-2-일메톡시이미노-1-(3-퀴놀리닐)시클로헥산카르보티오아미드
    AF (±)-안티-N-메틸-2-페네틸옥시이미도-1-(3-퀴놀리닐)시클로헥산카르보티오아미드
    AG (±)-안티-N-메틸-2-나프트-1-일메톡시이미노-1-(3-퀴놀리닐)시클로헥산카르보티오아미드
    AH (±)-안티-N-메틸-2-(3-삼차 부틸아미노-2-히드록시 프로폴시이미노-1-(3-퀴놀리닐)시클로헥산카르보티오아미드
    AI (±)-안티-N-메틸-2-이소프로폭시이미노-1-(3-퀴놀리닐)시클로헥산카르보티오아미드
    AJ (±)-안티-N-메틸-2-(4-히드록시벤질옥시이미노)-1-(3-퀴놀리닐)시클로헥산카르보티오아미드
    AK (±)-안티-N-메틸-2-(4-플루오로벤질옥시이미노)-1-(3-퀴놀리닐)시클로헥산카르보티오아미드
    AL (±)-안티-N-메틸-2-(4-플루오로벤질옥시이미노)-1-(3-피리딜)시클로헥산카르보티오아미드
    AM (±)-안티-N-메틸-2-(2,3,4,5,6,-펜타플루오로벤질옥시-이미노)-1-(3-피리딜)시클로헥산카르보티오아미드
    AN (±)-안티-N-메틸-2-이소프로폭시이미노-1-(3-피리딜)-시클로헥산카르보티오아미드
    AO (±)-안티-N-메틸-2-삼차 부톡시이미노-1-(3-피리딜)-시클로헥산카르보티오아미드
    AP (±)-안티-N-메틸-2-[4-(3-삼차부틸아미노-2-히드록시-프로폭시)벤질옥시이미노]-1-(3-피리딜)-시클로헥산-카르보티오아미드
    AQ (±)-안티-N-메틸-2-(4-히드록시벤질옥시이미노)-1-(3-피리딜)시클로헥산카르보티오아미드
    AR (±)-안티-N-메틸-2-(3-플루오로벤질옥시이미노)-1-(3-피리딜)시클로헥산카르보티오아미드
    AS (±)-안티-N-메틸-2-(2-플루오로벤질옥시이미노)-1-(3-피리딜)시클로헥산카르보티오아미드
    AT (±)-안티-N-메틸-2-(3-피리딜메톡시이미노)-1-(3-피리딜)시클로헥산카르보티오아미드
    AU (±)-안티-N-메틸-2-(4-니트로벤질옥시이미노)-1-(3-피리딜)시클로헥산카르보티오아미드
    AV (±)-안티-N-메틸-2-(4-시아노벤질옥시이미노)-1-(3-피리딜)시클로헥산카르보티오아미드
    AW (±)-안티-N-메틸-2-(3,4-디플루오로벤질옥시이미노)-1-(3-피리딜)시클로헥산카르보티오아미드
    AX (±)-안티-N-메틸-2-(4-메톡시벤질옥시이미노)-1-(3-피리딜)시클로헥산카르보티오아미드
    AY (±)-안티-N-메틸-2-(2-트리플루오로베틸벤질옥시-이미노)-1-(3-피리딜)시클로헥산카르보티오아미드
    AZ (±)-안티-N-메틸-2-(4-이소퀴놀리닐)시클로헥산-카르보티오아미드
    BA (±)-안티-N-메틸-2-벤질옥시이미노-1-(4-이소퀴놀리닐)-시클로헥산카르보티오아미드
    BB (±)-N-메틸-2-옥소-1-(5-피리미딜)시클로헥산-카르보티오아미드
    BC (±)-N-메틸-2-옥소-1-(3-피리딜)시클로펜탄-카르보티오아미드
    BD (±)-안티-N-메틸-2-(4-플루오로벤질옥시이미노)1-(3-피리딜)시클로펜탄산카르보티오아미드
    BE (±)-안티-N-메틸-2-메톡시이미노-1-(3-피리딜)-시클로펜탄산카르보티오아미드
    BF (±)-안티-N-메틸-2-벤질옥시이미노-1-(3-피리딜)시클로펜탄산카르보티오아미드 또는 제약학적으로 허용가능한 그 염으로서 확인된 화합물.
  8. 하기(A)-(E)를 포함하는, 제1항에 나타낸 일반식(Ⅰ)의 티오포름아미드 유도체의 제조 방법 ;-(A) X가 카르보닐기 또는 R1이 제1항에서 정의된 바와 같은 일반식 〉C=NOR1또는 〉C=NN(R1)2의 기를 나타내고 Y, R 및 Het가 제1항에서 정의된 바와 같은 경우, 하기 일반식(Ⅲ)의 화합물을 하기 일반식(Ⅳ)의 이소티오시아네이트와 반응:
    상기식에서 X'은 카르보닐 기 또는 제1항에서 정의된 바와 같은 일반식 〉C=NOR1또는 〉C=NN(R1)2의 기를 나타내고 Y 및 Het는 제1항에서 정의된 바와 같다;
    R-N=C=S (Ⅳ)
    상기식에서 R은 1-4개의 탄소 원자를 함유하는 직쇄 또는 측쇄 알킬 라디칼을 나타낸다. (B) X가 카르보닐 기를 나타내는 경우 Y 및 Het가 제1항에서 정의된 바와 같고 X'가 카르보닐 기를 나타내는 일반식(Ⅲ)의 거울상이성질체의 혼합물을 키랄 보조제와 입체성 선택 반응시키고 얻어진 생성물을 R이 제1항에서 정의된 바와 같은 일반식 R-N=C-S (Ⅳ)의 화합물과 반응시킨뒤 키랄 보조제의 제거 : (C) X가 히드록시메틸렌 기를 나타내고 Y, R 및 Het가 제1항에서 정의된 바와 같은 경우, X가 카르보닐 기를 나타내고 Y, R 및 Het가 제1항에서 정의된 바와 같은 일반식(Ⅰ)의 화합물의 환원; (D) X가 제1항에서 정의된 바와 같은 일반식 〉C=NOR1또는 〉C=NN(R1)2또는 〉=C=NN(R1)CON(R1)2의 기를 나타내고, Y, R 및 Het가 제1항에서 정의된 바와 같은 경우, X가 카르보닐기를 나타내는 일반식(Ⅰ)의 화합물을 R1이 제1항에서 정의된 바와 같은 일반식
    의 화합물 또는 그 산부가염과의 반응; (E) R이 메틸 라디칼을 나타내고 X가 카르보닐기 또는 제1항에서 정의된 바와 같은 일반식 〉C=NOR1또는 〉C=NN(R+)2의 기를 나타내는 경우, 메틸아민을 하기 일반식(Ⅵ)의 디티오에스테르의 반응
    상기식에서 R1은 1-4개의 탄소 원자를 함유하는 직쇄 또는 측쇄 알킬 라디칼, 또는 벤질 또는 카르복시메틸 라디칼을 나타내고, X'는 상기에서 정의된 바와 같고 Y 및 Het는 제1항에서 정의된 바와 같다; 그 후 임의로 얻어진 티오포름아미드 유도체를 제약학적으로 허용가능한 그 염으로 전환시키는 단계.
  9. 제1항에서 정의된 바와 같은 일반식(Ⅰ)의 티오포름아미드 유도체 또는 제약학적으로 허용가능한 담체 또는 피복물과 관련된 제약학적으로 허용가능한 그 염을 포함하는 제약학적 조성물.
  10. Y및 Het가 제1항에서 정의된 바와 같고 X'가 제8항에서 정의된 바와 같은(단,Y는 Het가 임의로 치환된 피라진-2-일 기를 나타내는 경우 직접 결합이 아니며 Het가 임의로 치환된 인돌-3-일 기를 나타내는 경우 메틸렌을 나타내지 않는다) 제8항에서 지시된 일반식(Ⅲ)의 화합물.
  11. 제1항에서 정의된 바와 같은 일반(Ⅰ)의 티오포름아미드 유도체 또는 제약학적으로 허용가능한 그염을 국부적으로 투여하는 것을 포함하는 남성형 대머리와 연과된 머리카락 손실의 저해 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019880016914A 1987-12-18 1988-12-16 티오포름아미드 유도체, 이를 포함하는 조성물 및 그 제조 방법 KR890009871A (ko)

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