KR890014470A - 카르바펜엠 중간체의 제조방법 - Google Patents

카르바펜엠 중간체의 제조방법 Download PDF

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KR890014470A
KR890014470A KR1019890003685A KR890003685A KR890014470A KR 890014470 A KR890014470 A KR 890014470A KR 1019890003685 A KR1019890003685 A KR 1019890003685A KR 890003685 A KR890003685 A KR 890003685A KR 890014470 A KR890014470 A KR 890014470A
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alkyl
enyl
azetidin
carboxyprop
producing
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KR1019890003685A
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KR0125932B1 (ko
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쇼이찌로 우에오
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요시또시 가즈오
시오노기세이야꾸 가부시끼가이샤
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
    • C07D477/02—Preparation
    • C07D477/04—Preparation by forming the ring or condensed ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Automobile Manufacture Line, Endless Track Vehicle, Trailer (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

내용 없음.

Description

카르바펜엠 중간체의 제조방법
내용없음

Claims (25)

  1. 4-(이탈기 치환된) 아제티딘-2-온(Ⅰ)을 식(Ⅲ)의 트랜스-2-(이탈기 치환된)메틸-3-알킬아크릴산과 환원성 금속으로 반응시킴을 특징으로 하는 4β(1β-알킬-2-카르복시프로프-2-엔일)아제티딘-2-은(Ⅱ)의 제조방법.
    (상기식에서, R1은 수소 또는 임의로 치환된 알킬 ; R2는 임의로 치환된 알킬 ; R3은 수소 또는 카르복시보호기 ; 그리고 R4와 R5는 각각 이탈기이다.)
  2. 제1항에 있어서, R1이 1C 내지 10C 알킬 3C 내지 18C 히드로카르빌실릴로 임의로 보호된 1C 내지 10C 히드록시알킬, 1C 내지 8C 할로알킬, 또는 4C 내지 8C 디옥소렌일인 4β-(1β-알킬-2-카르복시프로프-2-엔일)아제티딘-2-온(Ⅱ)의 제조방법.
  3. 제1항에 있어서, R1이 수소, 1C 내지 8C 알킬, 또는 1C 내지 8C 1-(임의로 보호된 히드록시 또는 할로) 알킬인 4β-(1β-알킬-2-카르복시프로프-2-엔일)아제티딘 -2-온(Ⅱ)의 제조방법.
  4. 제3항에 있어서, 임의의 보호기가 1C 내지 10C카르복실계 아실, 2C 내지 10C카르본계 아실, 2C 내지 8C 에테르 형성기, 3C 내지 18C 트리히드로카르빌실릴, 7C 내지 19C 반응성 아르알킬 인 4β-(1β-알킬-2-카르복시프로프-2-엔일)아제티딘-2-온-(Ⅲ)의 제조방법.
  5. 제1항에 있어서, R1이 1-히드록시에틸, 1-(3차-부틸디메틸실옥시)에틸, 또는 1-(트리에틸실릴-옥시)에틸인 4β-(1β-알킬-2-카르복시프로프-2-엔일)아제티딘-2-온(Ⅱ)의 제조방법.
  6. 제1항에 있어서, R2가 1C 내지 8C알킬 또는 치환된 알킬인 4β-(1β-알킬-2-카르복시프로프-2-엔일)아제티딘-2-온(Ⅱ)의 제조방법.
  7. 제1항에 있어서, R2가 1C 내지 3C알킬 또는 1C 내지 5C 할로겐알킬인 4β-(1β-알킬-2-카르복시프로프-2-엔일)아제티딘-2-온(Ⅱ)의 제조방법.
  8. 제1항에 있어서, R2가 메틸 또는 에틸 인 4β-81β-알킬-2-카르복시프로프-2-엔일)아제티딘-2-온(Ⅱ)의 제조방법.
  9. 제1항에 있어서, R3가 수소 또는 1C 내지 8C알킬인 4β-(1β-알킬-2-카르복시프로프 -2-엔일)아제티딘-2-온(Ⅱ)의 제조방법.
  10. 제1항에 있어서, R3가 수소, 메틸 또는 에틸인 4β-(1β-알킬-2-카르복시프로프-2-엔일)아제티딘-2-온(Ⅱ)의 제조방법.
  11. 제1항에 있어서, R4와 R5가 각각 불소, 염소, 브롬, 또는 임의로 치환된 1C 내지 8C 알칸오일옥시, 7C 내지 15C 아로일옥시, 1C 내지 8C 알킬술폰일옥시, 1C 내지 8C 치환된 알킬술폰일옥시, 6C 내지 10C 아릴술폰일옥시, 1C 내지 8C 알킬술핀일, 또는 6C 내지 10C 아릴술핀일 인 4β-(1β-알킬-2-카르복시프로프-2-엔일)아제티딘-2-온(Ⅱ)의 제조방법.
  12. 제11항에 있어서, R4가 아세톡시이고 R5가 브롬인 4β-(1β-알킬-2-카르복시프로프-2-엔일)아제티딘-2-온(Ⅱ)의 제조방법.
  13. 제1항에 있어서, 반응을 용매중에서 수행하는 4β-(1β-알킬-2-카르복시프로프-2-엔일)아제티딘-2-온(Ⅱ)의 제조방법.
  14. 제13항에 있어서, 용매가 테트라히드로푸란인 4β-(1β-알킬-2-카르복시프로프-2-엔일)아제티딘-2-온(Ⅱ)의 제조방법.
  15. 제1항에 있어서, 환원성 금속이 -0.1 내지 -0.8 볼트의 산화-환원 전위를 갖는 4β-(1β-알킬-2-카르복시프로프-2-엔일)아제티딘-2-온(Ⅱ)의 제조방법.
  16. 제1항에 있어서, 환원성 금속이 아연인 4β-(1β-알킬-2-카르복시프로프-2-엔일)아제티딘-2-온(Ⅱ)의 제조방법.
  17. 제16항에 있어서, 아연을 브롬화제 2구리로 활성 화한 4β-(1β-알킬-2-카르복시프로프-2-엔일)아제티딘-2-온(Ⅱ)의 제조방법.
  18. 제1항에 있어서, 반응을 -10 내지 50℃에서 0.5 내지 10시간동안 수행하는 4β-(1β-알킬-2-카르복시프로프-2-엔일)아제티딘-2-온(Ⅱ)의 제조방법.
  19. 제18항에 있어서, 반응을 30 내지 35℃에서 3.5시간동안 수행하는 4β-(1β-알킬-2-카르복시프로프-2-엔일)아제티딘-2-온(Ⅱ)의 제조방법.
  20. 하기식(Ⅱ)의 4β-(1β-알킬-2-카르복시-프로프-2-엔일)아제티딘-2-온(Ⅱ).
    (상기식에서, R1은 수소 또는 임의로 치환된 알킬 : R2는 임의로 치환된 알킬 : 그리고 R3는 수소 또는 카르복시보호기이다.)
  21. 제20항에 있어서, R1이 1-히드록시에틸, 1-(3차-부틸디메틸실릴옥시)에틸, 또는 1-(트리에틸실릴옥시)에틸 ; R2가 메틸 또는 에틸 ; 그리고 R3가 수소, 메틸, 또는 에틸인 4β-(1β-알킬-2-카르복시프로프-2-엔일)아제티딘-2-온(Ⅱ)화합물.
  22. 제1항에 있어서의 방법의 조합 및 전술한 방법과 실질적으로 동종의 반응으로 이루어진 항균물질 1-카르바펜-2-엠 화합물의 제조방법.
  23. 실질적으로 전술한 반응을 거쳐 제조된 항균물질 1-카르바펜-2-엠 화합물.
  24. 제23항에 있어서, 전술한 실시예에 기술된 것과 실질적으로 동일한 반응에 의해 제조된 항균물질 1-카르바펜-2-엠 화합물.
  25. 활성 성분으로서, 제23항에 청구된 1-카르바펜-2-엠을 함유하는 항균성 제제.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019890003685A 1988-03-23 1989-03-23 카르바펜엠 중간체의 제조방법 KR0125932B1 (ko)

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JP63-70763 1988-03-23
JP7076388 1988-03-23
JP070763/1988 1988-03-23

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KR0125932B1 KR0125932B1 (ko) 1997-12-26

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US (1) US4960879A (ko)
EP (1) EP0336143B1 (ko)
KR (1) KR0125932B1 (ko)
AT (1) ATE90343T1 (ko)
AU (1) AU613724B2 (ko)
CA (1) CA1340115C (ko)
DE (1) DE68906945T2 (ko)
ES (1) ES2017596T3 (ko)
GB (1) GB2216525B (ko)

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CA2000565C (en) * 1988-10-19 1998-06-23 Masaji Ishiguro Process for the preparation of 4-acyloxy-2-azetidinone derivatives
US4992545A (en) * 1989-09-20 1991-02-12 Eli Lilly And Company Process for preparing 4-substituted azetidinones
JPH03120280A (ja) * 1989-10-03 1991-05-22 Shionogi & Co Ltd ハロメチルカルバペネム化合物の製法
FI96311C (fi) * 1989-12-04 1996-06-10 Squibb Bristol Myers Co Menetelmä farmaseuttisesti käyttökelpoisten 6-(1-hydroksietyyli)-3-(substituoitu tio)-7-okso-1-atsabisyklo/3.2.0/hept-2-eeni-2-karboksyylihappojohdannaisten valmistamiseksi
US5672701A (en) * 1990-01-16 1997-09-30 Bristol-Myers Squibb Company 4-substituted alkyl carbapenem antibiotics
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EP0695753A1 (en) * 1994-08-05 1996-02-07 Zeneca Limited Carbapenem derivatives containing a bicyclic substituent, process for their preparation, and their use
US5607928A (en) * 1994-08-05 1997-03-04 Zeneca Limited Carbapenem derivatives containing a bicyclic ketone substituent and their use as anti-infectives
US6216687B1 (en) 1996-03-22 2001-04-17 The Majestic Products Company Unvented heating appliance having system for reducing undesirable combustion products
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US6346617B1 (en) 1997-08-26 2002-02-12 Merck & Co., Inc. Crystalline 2-hydroxymethyl carbapenem intermediate compounds and process for synthesis thereof
JP2001514169A (ja) * 1997-08-27 2001-09-11 メルク エンド カムパニー インコーポレーテッド β−メチルカルバペネム中間体の製造
US6143885A (en) * 1997-08-27 2000-11-07 Merck & Co., Inc. Preparation of beta-methyl carbapenem intermediates
US7632828B2 (en) * 2004-06-10 2009-12-15 Fob Synthesis, Inc. Gram-positive carbapenem antibacterials and processes for their preparation

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ATE10838T1 (de) * 1980-02-28 1985-01-15 Fujisawa Pharmaceutical Co., Ltd. 4-substituierte 2-oxoazetidin-verbindungen, verfahren zu deren herstellung und ihre verwendung zur antibiotika-herstellung.
JPS60158167A (ja) 1984-01-27 1985-08-19 Sumitomo Chem Co Ltd β−ラクタム化合物の製造法
EP0180189B1 (en) * 1984-10-31 1991-01-23 Sumitomo Pharmaceuticals Company, Limited Novel beta-lactams and their production
DE3509769A1 (de) * 1985-03-19 1986-09-25 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung von carbapenemzwischenprodukten
JPS6229577A (ja) 1985-07-31 1987-02-07 Sumitomo Pharmaceut Co Ltd オキサゾリジン誘導体
JPS62103063A (ja) * 1985-10-29 1987-05-13 Sagami Chem Res Center アゼチジノン誘導体の製造方法

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GB2216525A (en) 1989-10-11
GB2216525B (en) 1992-01-02
US4960879A (en) 1990-10-02
AU613724B2 (en) 1991-08-08
DE68906945D1 (de) 1993-07-15
ATE90343T1 (de) 1993-06-15
EP0336143B1 (en) 1993-06-09
CA1340115C (en) 1998-11-03
KR0125932B1 (ko) 1997-12-26
ES2017596A4 (es) 1991-03-01
DE68906945T2 (de) 1993-10-14
ES2017596T3 (es) 1994-10-16
EP0336143A1 (en) 1989-10-11
GB8906597D0 (en) 1989-05-04
AU3159989A (en) 1989-09-28

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