KR910000588A - 19-하이드록실라제 억제제로 유용한 19-치환된 프로게스테론 유도체 - Google Patents

19-하이드록실라제 억제제로 유용한 19-치환된 프로게스테론 유도체 Download PDF

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KR910000588A
KR910000588A KR1019890008839A KR890008839A KR910000588A KR 910000588 A KR910000588 A KR 910000588A KR 1019890008839 A KR1019890008839 A KR 1019890008839A KR 890008839 A KR890008839 A KR 890008839A KR 910000588 A KR910000588 A KR 910000588A
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워워 홀버트 젠
오 닐 죤스튼 죤
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개리 디. 스트릿
메렐 다우 파마슈티칼즈 인코포레이티드
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    • C07J41/005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of only two carbon atoms, e.g. pregnane derivatives
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    • C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
    • C07J5/0007—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond not substituted in position 17 alfa
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    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
    • C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
    • C07J7/0015—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa
    • C07J7/002—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa not substituted in position 16
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    • C07—ORGANIC CHEMISTRY
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    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
    • C07J7/0065—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by an OH group free esterified or etherified
    • C07J7/007—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by an OH group free esterified or etherified not substituted in position 17 alfa
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    • C07—ORGANIC CHEMISTRY
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Abstract

내용 없음

Description

19-하이드록실라제 억제제로 유용한 19-치환된 프로게스테론 유도체
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (11)

  1. 하기일반식의 혼합물.
    상기식에서 R1은 수소, 하이드록시 또는이고;R2는 (H)(H), (H)(OH) 또는 0이고, R3는 CH≡C-(CH2)n-, CH2=CH-(CH2)n-, Y-C≡C-CH2-, CH2=C=CH-, 사이클로프로필-N(R)-(CH2)n- 또는 R7-S-(CH2)n-이고, R4는 =0, (H)(OH), (H)(OR8) 또는 =CH2이고, R5는 수소, 아미노, 하이드록시, 옥소 또는 메틸렌이고, R6는 C1-6알킬, C5-7사이클로알킬 또는 페닐이고, R7는 수소, C1-6알킬, 사이클로프로필, C2-6알카노일, 벤조일 또는 트리플루오로아세틸이고, R8는 C2-6알카노일이고, R는 수소 또는 메틸이고, Y는 염소, 브롬 또는 요오드이고, n는 1내지 4의 정수이고, 각 점선은 임의로 존재하는 이중 결합을 가리키며, 단 5,6-(이중결합)은 R4가(H)(OH) 이거나 4,5-위치 또는 6,7-위치에 이중 결합이 없는 경우에만 존재하고 9,11-이중결합은 R2가 (H)(H)인 경우에만 존재할 수 있다.
  2. 제1항에 있어서, 하기 일반식의 화합물.
    상기식에서, R1은 수소, 하이드록시 또는이고;R2는 (H)(H), (H)(OH) 또는 0이고, R4는 =0, (H)(OH), (H)(OR8) 또는 =CH2이고, R6는 C1-6알킬, C5-7사이클로알킬 또는 페닐이고, 각 점선은 임의로 존재하는 이중 결합을 가리키며, 단 5,6-(이중결합)은 R4가(H)(OH) 이거나 4,5-위치 또는 6,7-위치에 이중 결합이 없는 경우에만 존재하고 9,11-이중결합은 R2가 (H)(H)인 경우에만 존재할 수 있다.
  3. 제1항에 있어서, 10-(2-프로피닐)-19-노르프레근-4-엔-3,20-디온 화합물.
  4. 제1항에 있어서, 21-하이드록시-10-(2-프로피닐)-19-노프프레근-4-엔-3,20-디온 화합물.
  5. 제1항에 있어서, 10-(1,2-프로파디에닐)-19-노르프레근-4-엔-3,20-디온 화합물.
  6. 제1항에 있어서, 19-사이클로프로필아미노르프레근-4-엔-3,20-디온 화합물.
  7. 제1항에 있어서, 19-머캅토프레근-4-엔-3,20-디온 화합물.
  8. 제1항에 있어서, 19-머캅토프레근-4-엔-3,20-디온 트리플루오로아세테이트화합물.
  9. (a) 10-(2-프로피닐)-20-메톡시-19-노르프레그나-5,17(20)-디엔-21-오에이트를 하이드라이드 환원제를 환원시켜 상응하는 21-하이드록시 화합물을 수득한 다음 표준공정에 의해 보호 그룹을 제거하거나, (b) 적절한 5α, 10α-에폭시-19-노르프레그난을 프로파길마그네슘 브로마이드와 반응시켜 상응하는 5α-하이드록시-10β-프로파길-19-노르프레그난을 수득한 다음 표준 공정에 의해 보호 그룹을 제거하고, 표준 시약을 사용하여 최종 생성물에서 목적한 바와 같은 케톤으로 어떤 3-하이드록시 그룹을 산화시키고, 어떤5-하이드록시 그룹을 산 제거하여 △4-화합물을 수득하거나, (c) 적절한 10-(1-아세톡시-2-프로피닐)-19-노르프레그난을 펜티닐 구리 및 부틸 리튬과 반응시켜 10-알레닌 그룹을 갖는 화합물을 수득한 다음 표준 공정에 의해 보호그룹을 제거하거나, (d) 적절한 프레그넨-19-알을 사이클로프로필 아민과 반응시켜 상응하는 19-사이클로프로필아미노 화합물을 수득한 다음 아민으로 하이드라이드 환원시키고 표준 공정에 의해 보호그룹을 제거하거나, (e) 적절한 19-하이드록시프레그난의 트리플루오로 메탄설포네이트 에스테르를 칼륨 에틸 크산토게네이트와 반응시킨 다음 가수분해하여 상응하는 19-머캅토프레그난을 수득함을 특징으로 하여, 제1항에 따른 하기 일반식의 화합물을 제조하는 방법.
    상기식에서 R1은 수소, 하이드록시 또는이고, R2는 (H)(H), (H)(OH) 또는 0이고, R3는 CH≡C-(CH2)n-, CH2=CH-(CH2)n-, Y-C≡C-CH2-, CH2=C=CH-, 사이클로프로필-N(R)-(CH2)n- 또는 R7-S-(CH2)n-이고, R4는 =0, (H)(OH), (H)(OR8) 또는 =CH2이고, R5는 수소, 아미노, 하이드록시, 옥소 또는 메틸렌이고, R6는 C1-6알킬, C5-7사이클로알킬 또는 페닐이고, R7는 수소, C1-6알킬, 사이클로프로필, C2-6알카노일, 벤조일 또는 트리플루오로아세틸이고, R8는 C2-10알카노일이고, R는 수소 또는 메틸이고, Y는 염소, 브롬 또는 요오드이고, n는 1내지 4의 정수이고, 각 점선은 임의로 존재하는 이중 결합을 가리키며, 단 5,6-(이중결합)은 R4가(H)(OH) 이거나 4,5-위치 또는 6,7-위치에 이중 결합이 없는 경우에만 존재하고 9,11-이중결합은 R2가 (H)(H)인 경우에만 존재할 수 있다.
  10. 제9항에 있어서, 메틸(E)-3,3-에틸렌디옥시-10-(2-프로피닐)-2-메톡시-19-노르프레그나-5,17(20)-디엔-21-오에이트를 디이소부틸알루미늄 하이드라이드로 환원시켜 상응하는 21-하이드록시 화합물을 수득한 다음 표준 공정에 의해 보호 그룹을 제거함으로써 21-하이드록시-10-(2-프로피닐)-19-노르프레근-4-엔-3,20-디온을 제조하는 방법.
  11. 제9항에 있어서, 메틸(E)-3,3-에틸렌디옥시-10-(2-프로피닐)-20-메톡시-19-노르프레그나-5,17(20)-디엔-21-오에이트를 디이소부틸알루미늄 하이드라이드로 환원시켜 상응하는 21-하이드록시 화합물을 수득하고, 이어서 피리디늄 P-톨루엔셀포네이트로 처리한 다음 메탄올성 염산으로 처리하여 보호 그룹을 제거함으로써 21-하이드록시-10-(2-프로피닐)-19-노르프레근-4-엔-3,20-디온을 제조하는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019890008839A 1988-06-28 1989-06-27 19-하이드록실라제 억제제로 유용한 19-치환된 프로게스테론 유도체 KR0160280B1 (ko)

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US07/212,409 US4910191A (en) 1988-06-28 1988-06-28 19-substituted progesterone derivatives useful as 19-hydroxylase inhibitors
US212,409 1988-06-28

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EP0348910B1 (en) 1995-05-17
FI893163A (fi) 1989-12-29
HU204066B (en) 1991-11-28
PH25714A (en) 1991-09-18
DK167534B1 (da) 1993-11-15
US4910191A (en) 1990-03-20
PT90988A (pt) 1989-12-29
EP0348910A3 (en) 1990-03-21
NO174511C (ko) 1994-05-18
FI92706C (fi) 1994-12-27
PT90988B (pt) 1994-11-30
ES2075014T3 (es) 1995-10-01
CN1039593A (zh) 1990-02-14
KR0160280B1 (ko) 1998-11-16
IL90727A (en) 1993-05-13
IL90727A0 (en) 1990-01-18
FI92706B (fi) 1994-09-15
CA1321578C (en) 1993-08-24
CN1033032C (zh) 1996-10-16
NO892678L (no) 1989-12-29
NO892678D0 (no) 1989-06-27
JPH0248598A (ja) 1990-02-19
ZA894754B (en) 1990-05-30
HUT51288A (en) 1990-04-28
DK318589A (da) 1989-12-29
FI893163A0 (fi) 1989-06-28
EP0348910A2 (en) 1990-01-03
NZ229696A (en) 1992-03-26
AU3712789A (en) 1990-01-04
DE68922660D1 (de) 1995-06-22
IE66338B1 (en) 1995-12-27
DE68922660T2 (de) 1996-01-18
NO174511B (no) 1994-02-07
IE892086L (en) 1989-12-28
DK318589D0 (da) 1989-06-27
AU610473B2 (en) 1991-05-16
JP2729320B2 (ja) 1998-03-18
ATE122681T1 (de) 1995-06-15

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