KR910009622A - 엔도-비시클로[2.2.1]헵탄-2-올의 효소 분할 방법 및 제조된 광학 활성 화합물 - Google Patents

엔도-비시클로[2.2.1]헵탄-2-올의 효소 분할 방법 및 제조된 광학 활성 화합물 Download PDF

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KR910009622A
KR910009622A KR1019900018244A KR900018244A KR910009622A KR 910009622 A KR910009622 A KR 910009622A KR 1019900018244 A KR1019900018244 A KR 1019900018244A KR 900018244 A KR900018244 A KR 900018244A KR 910009622 A KR910009622 A KR 910009622A
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bicyclo
hept
yloxy
exo
endo
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에이. 사코마노 니콜라스
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알렌 제이. 스피겔
화이자 인크
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Abstract

내용 없음.

Description

엔도-비시클로[2.2.1]헵탄-2-올의 효소 분할 방법 및 제조된 광학 활성 화합물
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 다음 구조식, (Ⅰ) 및 (Ⅱ)의 절대 입체 화학적 구조를 갖는 화합물로 구성된 군 중에서 선택된 광학 활성 화합물.
  2. 제1항에 있어서, 구조식(Ⅰ)을 갖는 화합물.
  3. 제1항에 있어서, 구조식(Ⅱ)을 갖는 화합물.
  4. 하기 구조식(Ⅴ) 및 (Ⅵ)의 절대 입체 화학적 구조를 갖는 화합물로 구성된 군 중에서 선택된 광학 활성 화합물.
    상기 각 식에서, Y는 -CN 또는 -CONH2이다.
  5. 제4항에 있어서, Y가 -CN인 화합물.
  6. 제4항에 있어서, Y가 -CONH2인 화합물.
  7. (a) 반응 불활성이고 실질적으로 무수인 유기 용매 중에서, 촉매량의 포유동물 췌장 리파제 존재 하에, 라세미 엔도-비시클로[2.2.1]헵탄-2-올 및 2,2,2-트리클로로에틸 부티레이트 간에 부분적으로 트란스에스테르화시켜 광학 활성인 (2S)-엔도-비시클로[2.2.1]헵탄-2-올과 (2R)-엔도-비시클로[2.2.1]헵탄-2-올의 부티르산 에스테르로 이루어진 혼합물을 형성하는 단계, (b) 상기 혼합물로 부터 상기의 (2S)-엔도-비시클로[2.2.1]헵탄-2-올을 분리하거나, 또는 상기의 혼합물로 부터 (2R)-엔도-비시클로[2.2.1]헵탄-2-올의 부티르산 에스테르를 분리하고, 이것을 통상의 방법으로 가수분해시켜 상기 (2R)-엔도-비시클로[2.2.1]헵탄-2-올을 제조하는 것을 특징으로 하는 광학 활성인 (2S)-엔도-비시클로[2.2.1]헵탄-2-올 또는 (2R)-엔도-비시클로[2.2.1]헵탄-2-올의 제조방법.
  8. 제7항에 있어서, 리파제가 돼지 유래인 것이 특징인 방법.
  9. 제7항 또는 제8항에 있어서, 반응 불활성 용매가 에테르인 것이 특징인 방법.
  10. 제7항 내지 제9항중 어느 한 항에 있어서, 추가로 (c) 상기 (2S)-엔도-비시클로[2.2.1]헵탄-2-올 또는 (2R)-엔도-비시클로[2.2.1]헵탄-2-올을 반응 불활성 용매 중에서, 약 50-100℃ 범위의 온도에서 각각 거의 1몰 당량의 트리페닐포스핀 및 디에틸아조디카르복실레이트 존재 하에 3-히드록시-4-메톡시-벤즈알데히드 1몰 당량 이상과 반응시켜 3-[(2R)-엑소-비시클로[2.2.1]헵트-2-일옥시]-4-메톡시벤즈알데히드 또는 3-[(2S)-엑소-비시클로[2.2.1]헵트-2-일옥시]-4-메톡시벤즈알데히드를 형성하는 단계, (d) 상기의 3-[(2R)-엑소-비시클로[2.2.1]헵트-2-일옥시]-4-메톡시벤즈알데히드 또는 3-[(2S)-엑소-비시클로[2.2.1]헵트-2-일옥시]-4-메톡시벤즈알데히드를 약 25-100℃ 범위의 온도에서 촉매량의 피페리딘 존재 하에서 피리딘 중의 2-시아노아세트산 2몰 당량 이상과 반응시켜서 3-(3-[(2R)-엑소-비시클로[2.2.1]헵트-2-일옥시]-4-메톡시페닐)펜탄디니트릴 또는 3-(3-[(2S)-엑소-비시클로[2.2.1]헵트-2-일옥시]-4-메톡시페닐)펜탄디니트릴을 얻는 단계, (e) 상기의 3-(3-[(2R)-엑소-비시클로[2.2.1]헵트-2-일옥시]-4-메톡시페닐)-펜탄디니트릴 또는 3-(3-[(2S)-엑소-비시클로[2.2.1]헵트-2-일옥시]-4-메톡시페닐)펜탄디니트릴을 통상의 방법으로 수화시켜 3-(3-[(2R)-엑소-비시클로[2.2.1]헵트-2-일옥시]-4-메톡시페닐)글루타르아미드 또는 3-(3-[(2S)-엑소-비시클로[2.2.1]헵트-2-일옥시]-4-메톡시페닐)글루타르아미드를 형성하는 단계, (f) 상기의 3-(3-[(2R)-엑소-비시클로[2.2.1]헵트-2-일옥시]-4-메톡시페닐)글루타르아미드 또는 3-(3-[(2S)-엑소-비시클로[2.2.1]헵트-2-일옥시]-4-메톡시페닐/글루타르아미드를 피리딘 중의 테트라아세트산납 과몰량 존재 하에서 고리화시켜 상기의 5-(3-[(2R)-엑소-비시클로[2.2.1]헵트-2-일옥시]-4-메톡시페닐)-3,4,5,6-테트라히드로피리미딘-2(1H)-온 또는 5-(3-[(2S)-엑소-비시클로[2.2.1]헵트-2-일옥시]-4-메톡시페닐)-3,4,5,6-테트라히드로피리미딘-2(1H)-온을 형성하는 단계를 포함하며, 상기의 (2S)-엔도-비시클로[2.2.1]헵탄-2-올 또는 (2R)-엔도-비시클로[2.2.1]헵탄-2-올을 각각 5-(3-[(2R)-엑소-비시클로[2.2.1]헵트-2-일옥시]-4-메톡시페닐)-3,4,5,6-테트라히드로피리미딘-2(1H)-온 또는 5-(3-[(2S)-엑소-비시클로[2.2.1]헵트-2-일옥시]-4-메톡시페닐)-3,4,5,6-테트라히드로피리미딘-2(1H)-온으로 전환시키는 것을 특징으로 하는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019900018244A 1989-11-13 1990-11-12 엔도-비시클로[2.2.1]헵탄-2-올의 효소 분할 방법 및 제조된 광학 활성 화합물 KR930004654B1 (ko)

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PCT/US1989/005228 WO1991007501A1 (en) 1989-11-13 1989-11-13 Enzymatic resolution of endo-bicyclo[2.2.1]heptan-2-ol and derived pharmaceutical agents
USPCT/US89/05228 1989-11-13

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KR930004654B1 KR930004654B1 (ko) 1993-06-02

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US5124455A (en) * 1990-08-08 1992-06-23 American Home Products Corporation Oxime-carbamates and oxime-carbonates as bronchodilators and anti-inflammatory agents
IE71647B1 (en) 1991-01-28 1997-02-26 Rhone Poulenc Rorer Ltd Benzamide derivatives
NZ246087A (en) * 1991-12-06 1995-04-27 Shionogi Seiyaku Kk Production of optically active norborneol from a racemic ester mixture using a microoganism or treated cells thereof
DE69332762T2 (de) * 1992-12-02 2003-08-14 Pfizer Cathecoldiether als selektive pde iv hemmungsmittel
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