KR880000430A - Bcd 트리사이클릭 에르골린 부분-구조 동족체 - Google Patents

Bcd 트리사이클릭 에르골린 부분-구조 동족체 Download PDF

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KR880000430A
KR880000430A KR1019870006071A KR870006071A KR880000430A KR 880000430 A KR880000430 A KR 880000430A KR 1019870006071 A KR1019870006071 A KR 1019870006071A KR 870006071 A KR870006071 A KR 870006071A KR 880000430 A KR880000430 A KR 880000430A
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린 후서 디안
메너트 샤우스 존
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일라이 릴리 앤드 캄파니
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Abstract

내용 없음

Description

BCD 트리사이클릭 에르골린 부분-구조 동족체
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (14)

  1. 하기 일반식(Ⅰ)의 피라졸로〔3,4-g〕퀴놀린, 피리도 〔2,3-g〕퀴나졸린, 티아졸로〔4,5-g〕퀴놀린, 옥사졸로〔4,5-g〕퀴놀린, 또는 피롤로〔3,4-g〕퀴놀린 유도체 또는 이들의 염.
    상기 식에서,
    (여기서, R1ca는 수소, 또는 (C1내지 C3) 알킬이고, R11및 R12는 독립적으로 수소 또는 (C1내지 C3) 알킬이며, R13은 수소, NR11R12, 또는 (C1내지 C3) 알킬이다)이고 ;
    C 및 D환은 트란스 융합되며 ;
    R1은 (C1내지 C3) 알킬, 알릴 또는 사이클로프로필메틸이고 ;
    R2,R3,R4및 R5는 하기 1) 내지 4) 중의 하나로서 정의되는데 ;
    1) R3,R4및 R5는 수소이고, R2는 CH2OH, CH2OCH3, CH2SCH3, CH2SOCH3,CH2SO2CH3, CO2R6또는 CONR7R8(여기서, R6는 H, (C1내지 C4) 알킬, 또는 벤질이고, R7및 R8은 독립적으로 수소, (C1내지 C4) 알킬, 페닐, 벤질 및 펜에틸 중에서 선택된다)이며,
    단 rac-(4aβ,8aα)-4,4a,5,6,7,8,9-옥타하이드로-2H-피라졸로〔3,4-g〕퀴놀린,rac-(4aβ,7β,8aα)-4,4a,5,6,7,8,9-옥타하이드로-1H-피라졸로〔3,4-g〕퀴놀린,및 rac-(4aβ,7β,8aα)-4,4a,5,6,7,8,9-옥타하이드로-피롤로〔3,4-g〕퀴놀린은 제외되거나,
    2) R2는 CH2OH, CH2OCH3, CH2SCH3, CH2SOCH3CH2SO2CH3, CO2R6또는 CONR7R8(여기서, R6,R7및 R8은 상기 정의한 바와 같다)이고, R3은 수소이며, R4및 R5는 결합하여 이중결합을 형성하거나,
    3) R2,R4및 R5는 수소이고, R3은 OH, NH2, NHCOR9또는 NHSO2NR9R10(여기서, R9및 R10은 독립적으로 H, (C1내지 C4) 알킬, 및 페닐 중에서 선택된다)이거나,
    4) R2및 R4는 수소이고, R3및 R5는 결합하여 =0 또는 =NOH를 형성한다.
  2. 제 1 항에 있어서, 피라졸로 〔3,4-g〕퀴놀린 유도체인 화합물.
  3. 제 1 항에 있어서, 피리도〔2,3-g〕퀴나졸린 유도체인 화합물.
  4. 제 1 항에 있어서, 티아졸로 〔4,5-g〕퀴놀린 유도체인 화합물.
  5. 제 1 항 내지 4 항 중의 어느 한 항에 있어서, R1이 n-프로필인 화합물.
  6. 제 1 항 내지 4 항 중의 어느 한 항에 있어서, R2,R3,R4및 R5가 제 1 항의 1)에 정의된 바와 같은 화합물.
  7. 제 1 항 내지 4 항 중의 어느 한 항에 있어서, R2,R3,R4및 R5가 제 1 항의 2)에 정의된 바와 같은 화합물.
  8. 제 1 항 내지 4 항 중의 어느 한 항에 있어서, R2,R3,R4및 R5가 제 1 항의 3)에 정의된 바와 같은 화합물.
  9. 제 1 항 내지 4 항 중의 어느 한 항에 있어서, R2,R3,R4및 R5가 제 1 항의 4)에 정의된 바와 같은 화합물.
  10. 하기 일반식(12a)의 6-옥소-트란스-1,2,4a,5,6,7,8,8a-옥타하이드로퀴놀린 유도체 또는 6-옥소-트란스-데카하이드로 퀴놀린 유도체.
    상기 식에서,
    R1은 (C1내지 C3) 알킬, 알릴 또는 사이클로프로필메틸이고 ;
    R2는 수소, CH2OH, CH2OCH3, CH2SCH3, CH2SOCH3,CH2SO2CH3, CO2R6또는 CONR7R8(여기서, R6는 수소, (C1내지 C4) 알킬, 또는 벤질이고; R7및 R8은 독립적으로 수소, (C1내지 C4) 알킬, 페닐, 벤질 및 펜에틸 중에서 선택된다)이며,
    R3는 수소, OH, NH2, NHCOR9또는 NHSO2NR9R10(여기서, R9및 R10은 독립적으로 수소, (C1내지 C4) 알킬, 및 페닐 중에서 선택된다)이거나, R3및 R5는 결합하여 =0 또는 =NOH를 형성하고 ;
    R4및 R5는 모두 수소이거나, 결합하여 탄소-탄소 결합을 형성하며, 단 R5가 R3와 결합하여 =0 또는 =NOH를 형성한 경우 R4가 수소인 경우는 제외되며 ;
    단, R2및 R3중 하나는 수소이고 다른 하나는 수소가 아니며, 또한 화합물의 상대 입체화학이 (3β, 4aα, 8aβ)이면 R2는 CO2R6가 아니다.
  11. 하기 일반식(21)의 트란스-데카하이드로퀴놀린 유도체.
    상기 식에서,
    R1은 (C1내지 C3) 알킬, 알릴 또는 사이클로프로필메틸이고 ;
    R6은 (C1내지 C4) 알킬 또는 벤질이며 ;
    R15및 R16은 (C1내지 C3)알킬이거나 결합하여 -(CH2)n-(여기서, n이 2 내지 4 이다)을 형성한다.
  12. 제 1 항 내지 9 항 중의 어느 한 화합물이 약제학적으로 허용되는 담체 또는 희석제와 혼합되어 함유된 약제학적 제제.
  13. 하기 일반식(7a)의 7-디메틸아미노메틸렌-6-옥소=트란스-퀴놀린 유도체를 일반식 NH2NHR10a(여기서, R10a는 수소 또는 (C1내지 C3)알킬이다)의 히드라진 또는 히드라진 유도체와 반응시켜 B환이 a) 또는 b)인 일반식(1)의 피라졸로 〔3,4-g〕퀴놀린 유도체를 수득하거나, 일반식(7a) 화합물을 일반식의 구아니딘 또는 구아니딘 유도체와 반응시켜 B환이 c)인 일반식(1)의 피리도〔2,3-g〕퀴나졸린 유도체를 수득하거나 ;
    하기 일반식(13a)의 7-브로모-6-옥소=트란스-퀴놀린 유도체를 일반식(R13a는 (C1내지 C3)알킬 또는 NR11R12이고, R11및 R12는 제 1 항에 정의한 바와 같다)의 티오우레아 또는 티오아미드와 반응시켜 B환이 d)이고 R13이 (C1내지 C3)알킬 또는 NR11R12인 일반식(1)의 티아졸로 〔4,5-g〕퀴놀린 유도체를 수득하거나, 일반식(13a) 화합물을 요소와 반응시켜 B환이 e)인 일반식(1)의 옥사졸로 〔4,5-g〕-퀴놀린 유도체를 수득하거나 ;
    B환이 d)이고 R13이 NR11R12인 일반식(1)의 티아졸로 〔4,5-g〕퀴놀린 유도체의 1 급 아민그룹을 디아조화시키고 디아조늄염을 치아인산으로 처리하여 B환이 d)이고 R13이 수소인 상응하는 일반식(1)의 티아졸로 〔4,5-g〕퀴놀린 유도체를 수득하거나 ;
    하기 일반식(10)의 2-아세틸-피롤로 〔3,4-g〕퀴놀린 화합물을 염기성 조건하에 가수분해시켜 B환이 f)인 일반식(1)의 피롤로 〔3,4-g〕퀴놀린 유도체를 수득하거나 ;
    R2가 CO2R6a이고 R6a가 (C1내지 C4)알킬 또는 벤질인 일반식(1)의 화합물을 가수분해시켜 R2가 CO2H인 상응하는 일반식(1)의 화합물을 수득하거나 ;
    R2가 CO2R6인 일반식(1)의 화합물을 환원시켜 R2가 CH2OH인 상응하는 일반식(1)의 화합물을 수득하거나 ;
    R2가 CH2CI 또는 CH2Br인 일반식(1)의 화합물로부터의 할라이드를 메틸머캅티드로 치환시켜 R2가 CH2SCH3인 상응하는 일반식(1)의 화합물을 수득하거나 ;
    R2가 CH2SCH3인 일반식(1)의 화합물을 산화시켜 R2가 CH2SOCH3인 상응하는 일반식(1)의 화합물을 수득하거나 ;
    R2가 CH2SCH3또는 CH2SOCH3인 일반식(1)의 화합물을 산화시켜 R2가 CH2SO2CH3인 상응하는 일반식(1)의 화합물을 수득하거나 ;
    일반식 NHR7R8의 아민을 R2가 CO2R6인 일반식(1)의 에스테르로 아실화시켜 R2가 CONR7R8인 일반식(1)의 화합물을 수득하거나 ;
    R3가 NHCOR9인 일반식(1)의 화합물을 가수분해시켜 R3가 NH2인 상응하는 일반식(1)의 화합물을 수득하거나 ;
    R8가 하이드록시인 일반식(1)의 화합물을 산화시켜 R3및 R5가 결합하여 옥소를 형성한 상응하는 일반식(1)의 화합물을 수득하거나 ;
    R3및 R5가 결합하여 옥소를 형성한 일반식(1)의 화합물을 하이드록실아민 또는 그의 염과 반응시켜 R3및 R5가 결합하여 하이드록시이미노를 형성한 일반식(1)의 화합물을 수득하거나 ;
    R1이 수소인 경우는 제외한 일반식(Ⅰ)의 화합물을 알릴 브로마이드 또는 알릴 클로라이드로 알킬화시켜 R1이 알릴인 상응하는 일반식(Ⅰ)의 화합물을 수득하거나;
    일반식(1)의 화합물을 염화(salifying)시킴을 특징으로 하여, 제 1 항에 정의된 일반식(1) 화합물을 제조하는 방법.
    상기 식에서,
    R1,R2,R3,R4및 R5는 제 1 항에서 정의된 바와 같다.
  14. 제13항의 방법에 의해 제조된 일반식(1)의 화합물.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019870006071A 1986-06-16 1987-06-16 Bcd 트리사이클릭 에르골린 부분-구조 동족체 및 이의 제조방법 KR890005302B1 (ko)

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DK299787D0 (da) 1987-06-12
HU197900B (en) 1989-06-28
US4826986A (en) 1989-05-02
NZ220650A (en) 1989-11-28
PT85061B (pt) 1990-03-30
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EP0250179A3 (en) 1989-08-23
AU7422987A (en) 1987-12-17
MX6887A (es) 1993-11-01
AT390061B (de) 1990-03-12
SU1644718A3 (ru) 1991-04-23
PT85061A (en) 1987-07-01
HUT44546A (en) 1988-03-28
CA1307526C (en) 1992-09-15
AU597073B2 (en) 1990-05-24
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PH25132A (en) 1991-02-19
ATA263287A (de) 1989-08-15

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