KR880013943A - 부분입체이성체 5R, 6S-6-(lR-하이드록시에틸)-2-(시스-l-옥소-3-티올라닐티오)-2-페넴-3-카복실산 - Google Patents

부분입체이성체 5R, 6S-6-(lR-하이드록시에틸)-2-(시스-l-옥소-3-티올라닐티오)-2-페넴-3-카복실산 Download PDF

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KR880013943A
KR880013943A KR1019880005398A KR880005398A KR880013943A KR 880013943 A KR880013943 A KR 880013943A KR 1019880005398 A KR1019880005398 A KR 1019880005398A KR 880005398 A KR880005398 A KR 880005398A KR 880013943 A KR880013943 A KR 880013943A
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알프레드 볼크만 로버트
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윌리암 데이비스 훈
화이자 인코포레이티드
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    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D499/88—Compounds with a double bond between positions 2 and 3 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
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Abstract

내용 없음

Description

부분입체이성체 5R,6S-6-(1R-하이드록시에틸)-2-(시스-1-옥소-3-티올라닐티오)-2-페넴-3-카복실산
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 하기 절대 입체화학 일반식(Ⅱ)의 페넴 또는 R이 수소인 경우 이의 약제학적으로 허용되는 양이온성 염.
    상기식에서, R은 수소 또는 생리학적 조건하에서 가수분해될 수 있는 에스테르를 형성하는 라디칼이다.
  2. 제1항에 있어서, R이 수소 또는 피발로일옥시메틸인 화합물.
  3. 하기 절대 입체화학 일반식(Ⅳ)의 화합물 또는 R5가 수소인 경우 이의 염.
    상기식에서, R4는 수소 또는 통상적인 실릴 하이드록시 보호그룹 이고; R5는 수소,또는이고; X는 수소 또는 클로로이고; 단, R4가 수소인 경우 R5는 CH2-CX=CH2이다.
  4. 제3항에 있어서, R4가 수소 또는 디메틸(t-부틸)실릴이고, R5가 -CH2-CX=CH|2이고, X가 클로로인 화합물.
  5. 하기 절대 입체화학 일반식(Ⅵ)의 화합물.
    상기식에서, R6는 통상적인 실릴 보호그룹이고; R7은 수소 또는이고; R10은또는이고; X는 수소 또는 클로로이다.
  6. 제5항에 있어서, R6가 디메틸(t-부틸)실릴이고, R7이 수소 또는인 화합물.
  7. 하기 절대 입체화학 일반식(Ⅷ)의 화합물.
    상기식에서, Y는 CH3CO, M또는 M 이고 M는 알카리 금속 양이온이다.
  8. 하기 절대 입체화학 일반식(ⅩⅠ)의 화합물.
    상기식에서 R8는 (C1-C3)알킬, 페닐 또는 p-톨릴이고, n은 0 또는 1이다.
  9. (a) 절대 입체화학 일반식(XIII)에 에폭사이드를 반응-불활성 용매중에서 알카리 금속 황화물의 작용에 의해 전환시켜 절대 입체화학 구조식(ⅩⅠ)의 화합물을 형성하고, (b)반응-불활성 용매중에서 구조식(ⅩⅠ)의 화합물을 통상적으로 설포닐화하여 절대 입체화학 일반식(Xa)의 화합물을 형성하고, (c)반응-불활성 용매중에서 일반식(Xa)의 화합물을 통상적으로 산화시켜 절대 입체화학 일반식(Xb)의 화합물을 형성하고, (d)일반식(Xb)의 화합물중 R8-SO2-O를 반응-불활성 용매중에서 알카리 금소 티오아세테이트로 통상적으로 친핵성 치환시켜 절대 입체화학 구조식(VIIIb)의 화합물을 형성하고, (e)구조식(VIIIb)의 화합물을 반응-불활성-용매중에서 CS2및 알카리 금속 알콕사이드의 작용에 의해 통상적으로 전환시켜 절대 입체화학 일반식(VIIIa)의 화합물을 형성하는 단계를 포함함을 특징으로 하는,
    절대 입체화학 일반식(VIIIa)의 화합물을 제조하는 방법.
    상기식에서, M는 알카리 금속 양이온이고, R8는 (C1-C3)알킬, 페닐 또는 톨릴이고, R9는 (C1-C3)알킬, 페닐 또는 p-톨릴이다.
  10. (a)절대 입체화학 일반식(XIV)의 화합물을 반응-불활성 용매중에서 CS2CO3와 반응시켜 절대 입체화학 구조식(XV)의 화합물을 형성하고 (b)구조식(XV)의 화합물을 반응-불활성 용매중 3급 아민의 존재하에 일반식 R9-SO2-Cl의 설포닐 클로라이드로 설포닐화시켜 절대 입체화학 일반식(XIII)의 화합물을 형성하는 단계를 포함함을 특징으로 하는, 절대 입체화학 일반식(XIII)의 화합물을 제조하는 개선된 방법.
    상기식에서, R9은(C1-C3)알킬, 페닐 또는 p-톨릴이다.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019880005398A 1987-05-11 1988-05-10 부분입체이성체 5r, 6r-6-(1r-하이드록시에틸)-2-(시스-1-옥소-3-티올라닐티오)-2-페넴-3-카복실산 KR900006840B1 (ko)

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USPCT/US87/01114 1987-05-11
PCT/US1987/001114 WO1988008845A1 (en) 1987-05-11 1987-05-11 Diastereomeric 5r,6s-6-(1r-hydroxyethyl)-2-(cis-1-oxo-3-thiolanylthio)-2-penem-3-carboxylic acids
USPCT/US/01114 1987-05-11

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KR900006840B1 KR900006840B1 (ko) 1990-09-22

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Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0352977A3 (en) * 1988-07-28 1991-08-07 Pfizer Inc. Stereoselective oxidation process
EP0382418A3 (en) * 1989-02-09 1991-10-23 Pfizer Inc. Process for optically active 3-thiolanyl sulfonate esters
US5321020A (en) * 1989-03-28 1994-06-14 Pfizer Inc. Antibacterial 2-carbapenem derivatives
HU209817B (en) * 1989-03-28 1994-11-28 Pfizer Process for the production of antibacterial 2-carbapenem derivatives
US5075439A (en) * 1990-08-17 1991-12-24 Pfizer Inc. Processes for (3S,4R)-3-[1(R)-t-butyl-dimethylsilyloxy)-ethyl]-4-[1-oxo-3-thiolanylthio(thiocarbonyl)thio]azetidin-2-ones and intermediates therefor
EP1712633A1 (en) * 2003-12-02 2006-10-18 Mercian Corporation Process for producing optically active tetrahydrothiophene derivative and method of crystallizing optically active tetrahydrothiophen-3-ol
JP2005314374A (ja) * 2004-03-31 2005-11-10 Daiso Co Ltd ３−ヒドロキシチオランの新規製法
KR100939347B1 (ko) 2005-07-20 2010-01-29 (주)카이로드 광학적으로 순수한 (ｓ)-3-히드록시 피롤리딘의 제조방법
PE20080940A1 (es) 2006-06-28 2008-07-09 Pfizer Prod Inc Profarmacos de penem
CN101479279B (zh) * 2006-06-28 2011-08-17 辉瑞产品公司 培南前药
US20080125408A1 (en) * 2006-11-14 2008-05-29 Pfizer Inc Penem prodrug
WO2008059367A1 (en) * 2006-11-14 2008-05-22 Pfizer Products Inc. Penem prodrugs
JP2010536385A (ja) 2007-08-24 2010-12-02 コデクシス， インコーポレイテッド （ｒ）−３−ヒドロキシチオランの立体選択的生成のための改善されたケトレダクターゼポリペプチド
CN105061394A (zh) * 2015-09-11 2015-11-18 北京工商大学 一种2-丙基-4-乙酰氧基四氢噻吩的制备方法
EP4382529A1 (en) 2022-12-07 2024-06-12 Bayer Consumer Care AG A process for preparing pure (3s)-pyrrolidin-3-ol and pure (3s)-pyrrolidin-3-ol hydrochloride

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4619924A (en) * 1984-05-18 1986-10-28 Pfizer Inc. 2-alkylthiopenem derivatives
EP0130025B1 (en) * 1983-06-21 1987-07-08 Pfizer Inc. 2-alkylthiopenem derivatives
US4739047A (en) * 1985-10-17 1988-04-19 Pfizer Inc. Intermediates for 2-(1-oxo-3-thiolanyl)-2-penem antibiotics
ZA867809B (en) * 1985-10-17 1988-05-25 Pfizer Process for 2-(1-oxo-3-thiolanyl)-2-penem antibiotics
EP0223397B1 (en) * 1985-10-17 1991-09-04 Pfizer Inc. Process for 2-(1-oxo-3-thiolanyl)-2-penem antibiotics
US4806637A (en) * 1986-03-17 1989-02-21 Schering Corporation 6-(Hydroxyethyl)-2-(heterocyclylthio)-penem-3-carboxylates
US4695626A (en) * 1986-07-29 1987-09-22 Pfizer Inc. 1-aza-4,5-dithiabicyclo [4.2.0] oct-2-en-8-one-2 carboxylate esters
PH24872A (en) * 1986-08-25 1990-12-26 Schering Corp (5r,6s,8r)-6-(-1-hydroxyethyl)-2-(3r-pyrrolidin-2-one-3-yl)thiopenem-3-carboxylic acid

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CN88102863A (zh) 1988-12-21
AU1589688A (en) 1988-11-17
EG18481A (en) 1993-06-30
IE70587B1 (en) 1996-12-11
KR900006840B1 (ko) 1990-09-22
DE3854874D1 (de) 1996-02-22
CS311988A2 (en) 1989-08-14
JPS63287781A (ja) 1988-11-24
IE881411L (en) 1988-11-11
PT87443A (pt) 1989-05-31
DK255888A (da) 1989-02-07
JPH0737463B2 (ja) 1995-04-26
US5013729A (en) 1991-05-07
CA1338830C (en) 1997-01-07
CN1023016C (zh) 1993-12-08
DK170443B1 (da) 1995-09-04
MY104306A (en) 1994-03-31

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