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KR840000581A - 새로운 스테로이드 유도체의 제조방법 - Google Patents

새로운 스테로이드 유도체의 제조방법 Download PDF

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KR840000581A
KR840000581A KR1019820002614A KR820002614A KR840000581A KR 840000581 A KR840000581 A KR 840000581A KR 1019820002614 A KR1019820002614 A KR 1019820002614A KR 820002614 A KR820002614 A KR 820002614A KR 840000581 A KR840000581 A KR 840000581A
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게로프지 튜쉬 쟝 (외 3)
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허버트 후리털
로우셀우크라프
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Abstract

내용 없음

Description

새로운 스테로이드 유도체의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (13)

  1. 다음의 구조식(Ⅱ)의 화합물을 케톤기능을 유리시킬 수 있는 탈수제와 반응시켜 구조식(I'A)의 화합물을 얻고, 이를 케탈화제와 작용시켜 3위치의 케톤기가 케탈형태로 차폐된 구조식(I'B)의 화합물을 얻거나. 또는 하이드록실아민 NH2OH나 NH2O-alk3형태로 차폐된 하이드록실아민과 작용시켜 구조식(I'C)의 화합물을 얻거나. 또는 케톤기를 선택적으로 환원시킬 수 있는 환원제와 반응시켜 구조식(I'D)의 화합물을 얻어서 필요할 경우 이를 alk1기를 도입시킬 수 있는 에스테르화제와 작용시켜 구조식(I'E)의 화합물을 얻거나. 또는 Coalk2그룹을 도입시킬 수 있는 에스테르화제와 작용시켜 구조식(I'F)의 화합물을 얻고, 구조식(I'A)의 화합물은 C=A가 CH2그룹인 유도체로 전환시키고. 또는 구조식 (I'A), (I'B), (I'C), (I'D), (I'E) 또는 (I'F)의 화합물은 산과 반응시켜 염을 얻거나 산화제와 반응시켜서 R1기가 질소원자를 함유하는 경우 그 질소원자가 산화되고 B와 C기는 에폭사이드 결합을 이루는 기를 11β 위치에 갖는 유도체를 얻거나. 또는 R1이 질소원자를 함유하지 않는 경우 B와 C가 에폭사이드 결합을 이루며 동시에 R1기는 산화된 질소를 함유하고 B와 C는 에폭사이드 결합을 이루고 있으며 그 결합은 R기에 함유된 산화된 질소원자 수준에서 선택적으로 환원되는 유도체를 얻어서. 필요할 경우 이를 산과 작용시켜 염으로 만드는 것을 특징으로 하는 다음의 구조식(I')와 같은 화합물의 제조방법.
    윗 구조식에서 ;
    R1은 타소수 1-18인 유기기로서 11위치의 탄소 근체에 적어도 하나의 질소. 인. 또는 실리콘 원자를 함유하며.
    R2는 탄소수 1-8인 탄화수소기를 나타내고
    X는 치환가능하며 불포화도 포함가능한 5각이나 6각 고리의 잔사를 나타내며,
    3위치의 C=A그룹은 케탈
    C=NOH 그룹, C=NO-alk3그룹, 또는 CH2그룹(alk1, alk2및 alk3는 탄소수 1-8인 알킬기나 탄소수 7-15인 아랄킬그룹을 의미한다) 형태로 유리되거나 차폐된 옥소그룹을 나타내고, B와 C는 함께
    이중 결합이나 에폭사이드 결합을 이루며, K는 케탈, 티오케탈, 옥심 또는 메틸옥심 형태로 차폐된 케톤 그룹을 의미한다.
  2. 구조식(Ⅱ)의 화합물을 케톤기를 유리시킬 수 있는 탈수제와 반응시락 구조식(I'A)의 화합물을 얻고 이를 케탈화제와 작용시락 3위치의 케톤기가 케탈형태로 차폐된 구조식(I'B)의 화합물을 얻거나, 또는 유리 하이드록실아민 NH2OH나 NH2O-alk3형태로 차폐된 하이드록실아민과 반응시켜 구조식(I'C)의 화합물을 얻거나, 또는 케톤기를 선택적으로 환원시킬 수 있는 환원제와 작용시락 구조식(I'D)의 화합물을 얻고 이를 필요하다면 alk1기를 도입시킬 수 있는 에테르화제와 반응시락 구조식(I'E)의 화합물을 얻거나 또는 CO alk2를 도입시킬 수 있는 에스테르화제와 작용시락 구조식(I'F)의 화합물을 얻으며, 혹은 앞의 구조식(I'A)의 화합물을 공지의 방법을 이용하여 C=A가 CH2그룹을 나타내는 유도체로 전환시키고 구조식(I'A), (I'B), (I'C), (I'D), (I'E) 또는 (I'F)의 화합물은 산과 작용시락 염을 얻는 것을 특징으로 하는 구조식(Ⅰ)에 해당되는 상기 1항에 따른 화합물의 제조방법
    이하 화합물(Ⅱ), (I'A), (I'B), (I'C), (I'D), (I'E) 그리고 (I'F)의 구조식은 상기 1항에서와 같다.
  3. 출발물질로서 R2가 메틸기인 구조식(Ⅱ)의 화합물이 사용되는 특징이 있는 상기 1항의 제조방법.
  4. X가와 같은 구조(16-17 위치의 점선은 이중결합의 가능성을 나타냄)의 잔사를 기타내고
    Y는기를 의미하는 구조식(Ⅱ)의 화합물을 출발물질로 하는 상기 1-3항에 따른 방법.
    위에서 n은 1이나 2인 정수, R5는 수소, 탄소수 1-8인 알킬기, 탄소수 2-8인 알키닐기나 알케닐기, 탄소수 6-14인 아릴기, 또는 탄소수 7-15인 아탈킬기를 의미하고, R6는 R5와 서로 같거나 다른 것으로서 상기에 언급한 것들의 에도하이드록실기를 나타낼 수도 있다.
    R3와 R4는 같거나 다른 것으로서 수소나 OH기 Oalk4나 O-CO-alk5(alk|4와 alk5는 탄소수 1-8인 알킬기나 탄소수 7-15인 아킬탈기를 의미한다)기, 탄소수 2-8인 알케닐이나 알키닐기기,기, -COCH2OCOalk6기(alk6는 탄소수 1-8인 알킬기나 탄소수 7-15인 아랄킬기를 의미한다), CO-CO2H기, CO-CO2-alk7기(alk|7은 탄소수 1-8인 알킬기이다), 또는기, 혹은기(alk8은 탄소수 1-8인 알킬기이거나 탄소수 7-15인 아랄킬기이다), -C≡N기이며,
    또는 R3와 R4는 함께기를 형성한다.
    (Z1은 탄소수 1-8인 아실이나 알킬기, 또는 수소이고 Z2는 탄소수 1-8인 알킬기이다)
  5. 고리 D가 어떠한 불포화 에틸렌기도 지니고 있지 않으며 R5와 R6는 수소이고 n은 1인 구조식(Ⅱ)의 화합물을 출발물질로 하는 상기 1,3 또는 4항에 따른 제조방법.
  6. R1이 탄소수 1-18인 기로서 적어도 하나의 질소를 함유하는 구조식(Ⅱ)의 물질을 출발물질로 하는 상기 1, 3-5항에 따른 제조방법.
  7. R1이 탄소수 1-8인 1차, 2차 혹은 3차 알킬기로서 산소, 질소, 황 가운데 하나 또는 그 이상의 이종원자를 포함하며 적어도 그 하나는 질소원자인 기이거나, 적어도 하나의 질소원자를 함유하며 탄소수 1-8인 알킬기로 치환 가능한 이종고리기이거나,
    아민기(R7과 R8은 탄소수 1-8인 알킬기, 또는 산소, 질소, 그리고 황 가운데 하나 또는 그 이상의 이종원자를 포함하며 그중 하나는 적어도 질소원자인 기이거나 적어도 하나의 질소원자가 포함된 이종고리로 치환된 기이다)이거나, 2-, 3-, 또는 4-피리딜기이거나,
    또는(n≥3)기,
    구조식(Ⅱ)의 화합물을 출발물로 하는 상기 6항에 따른 제조방법.
  8. 상기 2항에 정의된 바와같은 구조식(Ⅰ)의 화합물의 제조를 위한 상기 3-7항에 따른 제조방법.
  9. 구조식(Ⅲ)의 화합물을 구조가(R1)2Culi, R1MgHal 그리고 R1Li인 화합물로 구성되는 그룹에서 선택한 화합물과 반응시키는 것을 특징으로 하는 구조식(Ⅱ)의 화합물을 제조하기 위한 상기 1-8항에 따른 방법.
  10. 다음의 구조식(Ⅳ)의 화합물을 구조가 (R')2CuLi, R1MgHal, 그리고 R1Li인 화합물 가운데서 택한 물질과 구리 수화물 존재하에 작용시켜 구조식(Ⅴ)의 화합물을 얻고, 이를 환원제와 작용시켜 17-하이드록시 화합물을 얻거나, 또는 적절한 마그네슘 유도체와 작용시켜 17α-치환 17β-하이드록시 화합물을 얻거나, 또는 리툼이나 칼륨유도체와 같은 유기금속 유도체와 반응시켜 17α-치환 17β-하이드록시 화합물을 얻거나, 또는 시아니드화제와 반응시켜 17β-시아노 17α-하이드록시 화합물을 얻은 뒤, 유기금속유도체와 반응시켜 17α-치환 17β-하이드록시 화합물을 얻으며 필요하다면 위에서 얻은 17-하이드록시 화합물 중 어느 것을 에스테르화제나 에스테르화제와 반응시키고, 또 필요하다면 이를 17위치의 치환체가 3중 결합을 가지는 경우 환원제와 작용시켜 해당되는 에틸렌유도체를 얻는 것을 특징으로 하는 구조식(Ⅱ')와 같은 출발물질의 상기 1-8항에 따른 제조방법.
    윗 구조식에서
    R'3는 하이드록실기나 ORe기(Re는 잔사 alk4나 에테르그룹, 또는 에스테르그룹의 COalk5이다)를 나타내고, R'4는 수소, 혹은 탄소수 2-8인 일키닐이나 알케닐기를 의미한다.
  11. 구조식(I')의 화합물이
    -11β-[4-(N.N-디메틸아미노에틸옥시)페닐] 17β-하이드록시 17α-(프로-1-피닐)에스트라 4,9-디엔-3-은;
    -11β-(4-디메틸아미노페닐) 17β-하이드록시 17α-프로-1-피닐) 에스트라 4,9-디엔-3-은;
    -21-클로로 17β-하이드록시 11β-(4-디메틸아미노페닐)(17α) 19-노르프레그나 4,9-디엔-20-닌-3-은 N 옥사이드;
    -21-클로로 9α, 10α-에폭시 17β-하이드록시 11β-(4-디메틸아미노페닐) (17α) 19-노르프렌-4-염-20-닌-3-은 N 옥사이드;
    -17β-하이드록시 11β-(4-디메틸아미노페닐) 17α-(프로-2-피닐)에스트라 4,9-디엔-3-은, 그리고 -17β-하이드록시 11β-(4-디메틸아미노페닐) 17α-(프로-1-피닐) 에스트라 4,9-디엔-3-은인 것들 가운데 어느 하나가 제도되는 상기 1-6항에 따른 제조방법.
  12. 상기 1항의 구조식(Ⅱ)와 같은 새로운 공업용 화합물.
  13. 상기 10항의 구조식(Ⅴ)와 같은 새로운 공업용 화합물.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR8202614A 1981-01-09 1982-06-11 새로운 스테로이드 유도 체의 제조방법 KR870001936B1 (ko)

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HU185158B (en) 1984-12-28
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DK166680B1 (da) 1993-06-28
US4634695A (en) 1987-01-06
NL300001I1 (nl) 2000-04-03
EP0057115A3 (en) 1982-09-29
JPH01279897A (ja) 1989-11-10
FR2497807B1 (ko) 1983-07-29
ES8401498A1 (es) 1983-12-01
US4447424A (en) 1984-05-08
EP0057115B1 (fr) 1985-03-20
FR2497807A1 (fr) 1982-07-16
DK4082A (da) 1982-07-10
SG45987G (en) 1987-11-13
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US4386085A (en) 1983-05-31
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AU5123685A (en) 1986-04-17
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AU7929682A (en) 1982-07-15
DE19975073I2 (de) 2004-01-08
ZA8231B (en) 1982-11-24
NL300001I2 (nl) 2000-08-01
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GEP19960479B (en) 1996-07-22
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JPH0466879B2 (ko) 1992-10-26
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US4519946A (en) 1985-05-28
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