KR920021575A - 뉴클레오시드의 디아스테레오머를 선택적으로 합성하는 방법 - Google Patents

뉴클레오시드의 디아스테레오머를 선택적으로 합성하는 방법 Download PDF

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KR920021575A
KR920021575A KR1019920008507A KR920008507A KR920021575A KR 920021575 A KR920021575 A KR 920021575A KR 1019920008507 A KR1019920008507 A KR 1019920008507A KR 920008507 A KR920008507 A KR 920008507A KR 920021575 A KR920021575 A KR 920021575A
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엘. 췌 알란 에이취
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바이오켐 파르마 인코오포레이티드
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Abstract

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Description

뉴클레오시드의 디아스테레오머를 선택적으로 합성하는 방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (15)

  1. 하기 일반식(III)으로 표시되는 루이스산을 사용하여, 하기 일반식(II)로 표시되는 화합물의 단일 엔안티오머로 바람직한 퓨린 또는 피리미딘 염기 또는 그의 상도체 또는 유도체를 글리코실화 하는 단계를 포함하는 하기 일반식(I)로 표시되는 광학적으로 활성이 있는 시스-뉴클레오시드 및 뉴클레오시드 상동체 유도체를 디아스테레오머 선택적으로 제조하는 방법.
    상기식에서, R1은 수소 또는 아실; R2는 바람직한 퓨린 또는 피리미딘 염기 또는 그의 상동체 또는 유도체; W는 S, S=0, 또는 SO2, O, NZ, 또는 CH2; X는 0, S, S=0 또는 So2, O, NZ, CH2, CHF, CH, CHN3또는 CHOH; Y는 0, S. CH, CHF, 또는 CHOH; Z는 수소, 히드록실, 알킬 또는 아실; 이며 단 Y가 CH2이고 X가 0, S, S=0 또는 So2일때, W는 0, S, S=0 또는 So2가 아니며; R3는 치환된 카르보닐 또는 카르보닐 유도체; L은 이탈기; R5, R6및 R7은 각각 따로 수소; 플루오로, 브로모, 클로로, 요오드, C1-6알콕시 또는 C6-20아릴옥시로 임의 치환된 C1-20알킬; 할로겐, C1-20알킬 또는 C1-20알콕시로 임의 치환된 C7-20아르알킬; 플루오로, 브로모, 클로로, 요오드, C1-20알킬 또는 C1-20알콕시로 임의 치환된 C6-20아릴; 트리알킬실릴; 플루오로; 브로모; 클로로; 및 요오드로 구성된 군에서 선택된 것이고; R8은 플루오로; 브로모; 클로로; 요오드; 플루오로, 브로모, 클로로 또는 요오드로 임의 치환된 C1-20설포네이트 에스테르; 플루오로, 브로모, 클로로 또는 요오드로 임의 치환된 C1-20알킬 에스테르; 다가 할라이드; 일반식(R5)(R6)(R7) Si (여기에서 R5, R6, 및 R7은 상기 정의된 바와 같다)로 표시되는 삼중치환된 실릴기; 포화 또는 불포화된 셀레닐 C5-20아릴; 치환 또는 비치환된 C6-20아릴 설페닐; 치환 또는 비치환된 C6-20알콕시 알킬; 및 트리알킬 실록시기로 구성된 군중에서 선택된 것이다.
  2. 제1항에 있어서, 상기 글리코실화된 퓨린 또는 피리미딘 염기 또는 그의 상동체 또는 유도체의 R3를 환원시켜 일반식(I)로 표시되는 광학적으로 활성이 있는 시스-뉴클레오시스 또는 뉴클레오시드 상동체 또는 유도체를 제조하는 단계를 추가로 포함하는 방법.
  3. 제1항에 있어서, 상기 바람직한 퓨린 또는 피리미딘 염기물 글리코실화 하기전에 키랄 보조제를 사용하여 상기 일반식(II)의 화합물 단일 엔안티오머로 분할하는 단계를 추가로 포함하는 방법.
  4. 제1항 내지 제13항중 어느 한항에 있어서, R2가 피리미딘 염기인 방법.
  5. 제4항에 있어서, 상기 피리미딘염기는 시트신인 방법.
  6. 제4항에 있어서, 상기 피리미딘 염기는 5-플루오로시토신인 방법.
  7. 제1항 내지 제3항중 어느 한항에 있어서, 상기 루이스산은 트리메틸실린 트리플레이트와 요오드트리 메틸 실란으르 구성된 군에서 선택된 것인 방법.
  8. 제3항에 있어서, 상기 키랄 보조제는 (d)-멘톨 및 (1)-멘톨로 구성된 군에서 선택된 것인 방법.
  9. 제1항 내지 제3항중 어느 한항에 있어서, R3가 알콕시 카르보닐류, 카르복실류, 디에틸 카르복사미드, 피롤리딘 아미드, 메틸케톤 및 페닐케톤으로 구성된 군에서 선택된 것인 방법.
  10. 제9항에 있어서, R3가 알콕시카르보닐류 및 카르복실류로 구성된 군에서 선택된 것인 방법.
  11. 하기 일반식(II)로 표시되는 중간물질.
    상기식에서, W는 O, S=0, SO2, NZ 또는 CH2; X는 O, S=0, SO2, NZ, CH2CHF, CH, CHN3또는 CHOH; Y는 O, S, CH2, CH, CHF 또는 CHOH; Z는 수소, 히드록실, 알킬 또는 아실; 단 Y가 CH2이고 X가 O, S, S=0 또는 SO2일때, W는 O, S, S=0 또는 SO2가 아니며; R는 치환된 카르보닐 또는 카르보닐 유도체; L은 이탈기이다.
  12. 하기 일반식(VI)으로 표시되는 중간물질.
    상기식에서, W는 O, S=0, SO2, NZ 또는 CH2; X는 O, S=0, SO2, NZ, CH2CHF, CH 또는 CHN3또는 CHOH; Y는 O, S, CH2, CH, CHF 또는 CHOH; Z는 수소, 히드록실, 알킬 또는 아실; 단 Y가 CH2이고 X가 O, S, S=0 또는 SO2일때, W는 O, S, S=0 또는 SO2가 아니며; R3는 치환된 카르보닐 또는 카르보닐 유도체; R4는 키랄 보조제; L은 이탈기이다.
  13. 하기 일반식(VII)로 표시되는 중간물질.
    상기식에서, W는 O, S=0, SO2, NZ 또는 CH2; X는 O, S=0, SO2, NZ, CH2CHF, CH 또는 CHN3, 또는 CHOH; Y는 O, S, CH2, CH, CHF 또는 CHOH; Z는 수소, 히드록실, 알킬 또는 아실; 단 Y가 CH2이고 X가 O, S, S=0 또는 SO2일때, W는 O, S, S=0 또는 SO2가 아니며; R2는 퓨린 또는 피리미딘 염기 또는 그의 상동체 또는 유도체 이며; R3는 치환된 카르보닐 또는 카르보닐 유도체; R4는 키랄보조제이다.
  14. 하기 일반식(VIII)로 표시되는 중간물질.
    상기식에서, W는 O, S=0, SO2, NZ 또는 CH2; X는 O, S=0, SO2, NZ, CH2CHF, CH 또는 CHN3, 또는 CHOH; Y는 O, S, CH2, CH, CHF 또는 CHOH; Z는 수소, 히드록실, 알킬 또는 아실; 단 Y가 CH2이고 X가 O, S, S=0 또는 SO2일때, W는 O, S, S=0 또는 SO2가 아니며; R2는 퓨린 또는 피리미딘 염기 또는 그의 상동체 또는 유도체 이며; R3는 치환된 카르보닐 또는 카르보닐 유도체이다.
  15. 시스 및 트랜스-2R-카르보에톡시-5-히드록시테르라히드로푸란; 시스 및 트랜스-2S-카르보에톡시-5-히드록시테트라히드로푸란; 시스 및 트랜스-2R-카르보에톡시-5-아세톡시테트라히드로푸란; 시스 및 트랜스-2S-카르보에톡시-5-아세톡시테트라히드로푸란; 1'S-(N-4-아세틸 시토신-1-일)-4'R-카르보 에톡시테트라 히드로푸란; 1'S-(시토신-1-일)-4'R-카르보 에톡시테트라 히드로푸란; 1'R-(5-플루오로시토신-1-일)-4'S-카르보에톡시테트라 히드로푸란 및 1'S-(5-플루오로 시토신-1-일)-4'S-카르보에톡시테트라 히드로푸란; 및 1'S-(5-플루오로시토신-1-일)-4'R-카르보에톡시테트라 히드로푸란 및 1'R-(5-플루오로 시토신-1-일)-4'R-카르보에톡시테트라 히드로푸란으로 구성된 군에서 선택된 중간물질.
    ※ 참고사항:최초출원 내용에 의하여 공개되는 것임.
KR1019920008507A 1991-05-21 1992-05-20 뉴클레오시드의 부분 입체 이성체를 선택적으로 합성하는 방법 KR0160144B1 (ko)

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US70337991A 1991-05-21 1991-05-21
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HK1002431A1 (en) 1998-08-21
RU2105009C1 (ru) 1998-02-20
SK129493A3 (en) 1994-11-09
PL170869B1 (pl) 1997-01-31
IL101932A0 (en) 1992-12-30
CN1050603C (zh) 2000-03-22
JP3330972B2 (ja) 2002-10-07
FI106377B (fi) 2001-01-31
CZ249293A3 (en) 1994-03-16
OA10212A (en) 1997-10-07
AU1639592A (en) 1992-11-26
AU1690892A (en) 1992-12-30
ES2084937T3 (es) 1996-05-16
FI935151A (fi) 1993-11-19
WO1992020696A1 (en) 1992-11-26
AU655973B2 (en) 1995-01-19
HUT67471A (en) 1995-04-28
EP0515156B1 (en) 1996-02-07
CZ280857B6 (cs) 1996-04-17
IL116176A (en) 1998-02-08
DK0515156T3 (da) 1996-06-17
TWI245046B (en) 2005-12-11
BG98311A (bg) 1994-08-30
US5663320A (en) 1997-09-02
CZ249393A3 (en) 1994-04-13
NO921988L (no) 1992-11-23
RU2140925C1 (ru) 1999-11-10
WO1992020669A1 (en) 1992-11-26
DE69208144T2 (de) 1996-09-05
US5744596A (en) 1998-04-28
NO921988D0 (no) 1992-05-20
GT199800047A (es) 1999-08-26
IL116176A0 (en) 1996-01-31
HUT67726A (en) 1995-04-28
AU1691392A (en) 1992-12-30
EP0515157B1 (en) 1997-09-03
JP3229013B2 (ja) 2001-11-12
PL168910B1 (pl) 1996-05-31
PL176026B1 (pl) 1999-03-31
CN1035555C (zh) 1997-08-06
DE69221936D1 (de) 1997-10-09
CN1229078A (zh) 1999-09-22
HK132196A (en) 1996-07-26
BG61696B1 (bg) 1998-03-31
MX9202395A (es) 1993-02-01
IE921618A1 (en) 1992-12-02
MX9202404A (es) 1993-08-31
DK0515157T3 (da) 1997-09-29
IL101932A (en) 1997-04-15
CN1067245A (zh) 1992-12-23
GR3018941T3 (en) 1996-05-31
CN1067654A (zh) 1993-01-06
IE921619A1 (en) 1992-12-02
RO116812B1 (ro) 2001-06-29
FI109025B (fi) 2002-05-15
FI935150A (fi) 1993-11-19
NO300593B1 (no) 1997-06-23
SK281954B6 (sk) 2001-09-11
JP3704055B2 (ja) 2005-10-05
CA2069063A1 (en) 1992-11-22
AU1639492A (en) 1992-11-26
RU2163909C2 (ru) 2001-03-10
JPH05186465A (ja) 1993-07-27
DE69208144D1 (de) 1996-03-21
TW467907B (en) 2001-12-11
CN1038591C (zh) 1998-06-03
AU668086B2 (en) 1996-04-26
CN1097049C (zh) 2002-12-25
BG98310A (bg) 1994-01-03
CN1229079A (zh) 1999-09-22
JP2001354667A (ja) 2001-12-25
CN1229080A (zh) 1999-09-22
FI20001900A (fi) 2000-08-29

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