KR930017908A - 세펨 프로드럭(prodrug) 에스테르의 제조방법 - Google Patents

세펨 프로드럭(prodrug) 에스테르의 제조방법 Download PDF

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KR930017908A
KR930017908A KR1019930001929A KR930001929A KR930017908A KR 930017908 A KR930017908 A KR 930017908A KR 1019930001929 A KR1019930001929 A KR 1019930001929A KR 930001929 A KR930001929 A KR 930001929A KR 930017908 A KR930017908 A KR 930017908A
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acid
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데포싸 엘리자벳
피셔 게르트
게르라흐 우베
회롤라인 롤프
크라쓰 노르베르트
랏트렐 루돌프
슈타헤 울리히
볼만 테오도르
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테르가우, 바이쎄르트
훽스트 아크티엔게젤샤프트
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
    • C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
    • C07D501/34—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by carboxylic acids containing hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/587—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with aliphatic hydrocarbon radicals substituted by 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, said aliphatic radicals being substituted in the alpha-position to the ring by a hetero atom, e.g. with m >= 0, Z being a singly or a doubly bound hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • 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)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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  • Cephalosporin Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Diaphragms For Electromechanical Transducers (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

본 발명은 일반식(Ⅱ)의 화합물을 3급 아민의 존재하에 불활성 용매 중에서 일반식(Ⅵ)의 비스(벤조티아졸-2-일)디설파이드 및 트리페닐포스핀과 반응시켜 일반식(Ⅴ)의 화합물을 수득한 다음, 당해 화합물을 불활성 유기 또는 쌍극성 비양자성 용매 주에서 0내지 80℃의 온도에서 일반식(Ⅲ)의 7-아미노세프-3-엠-4-카복실산 에스테르와 반응시키고, 생성된 일반식(Ⅳ)의 옥심 보호된 화합물을 유기용매 중에서 20내지 110℃의 온도에서 무기산 또는 지방족 또는 설폰산으로 처리하여 일반식(I)의 화합물을 형성시킴을 포함하여, 일반식(I)의 세펨 프로드럭 에스테르를 제조하는 방법에 관한 것이다.
상기식에서, R1은 C1-C5-알카노일옥시-C1-C5-알킬 또는 C1-C5-알콕시카보닐옥시 -C1-C5-알킬이고, X는 무기 또는 유기 음이온이며, 하이드록시이미노 그룹은 syn-형태로 존재하고, R2는 산 가수분해에 의해 제거될 수 있는 보호 그룹이며, R3은 수소, C1-C5-알킬, C2-C5-알케닐, C3-C5-알키닐, C1-C5-알킬옥시, C2-C5-알케닐옥시, C3-C5-알키닐옥시, 하이드록시, 아세톡시, 니트로, 아미노, 카복실 또는 실포 그룹이고, 보호된 옥심 그룹은 syn-형태로 존재한다.

Description

세펨 프로드럭(prodrug)의 에스테르의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 일반식(Ⅱ)의 화합물을 3급 아민의 존재하에 불활성 용매 중에서 일반식(Ⅵ)의 비스(벤조티아졸-2-일)디설파이드 및 트리페닐포스핀과 반응시켜 일반식(Ⅴ)의 화합믈을 수득한 다음, 당해 화합물을 불활성 유기 또는 쌍극성 비양자성 용매 중에서 0내지 80℃의 온도에서 일반식(Ⅲ)의 7-아미노세프-3-엠-4-카복실산 에스테르와 반응시키고, 생성된 일반식(Ⅳ)의 옥심 보호된 화합물을 유기 용매 주에서 20내지 110℃의 온도에서 무기산 또는 지방족 또는 방향족 설폰산으로 처리하여 일반식(I)의 화합물을 형성시킴을 포함하여, 일반식(I)의 화합물을 제조하는 방법.
    상기식에서, R1은 C1-C5-알카노일옥시-C1-C5-알킬 또는 C1-C5-알콕시카보닐옥시 -C1-C5-알킬이고, X는 무기 또는 유기 음이온이며, 하이드록시이미노 그룹은 syn-형태로 존재하고, R2는 산 가수분해에 의해 제거될 수 있는 보호 그룹이며, R3은 수소, C1-C5-알킬, C2-C5-알케닐, C3-C5-알키닐, C1-C5-알킬옥시, C2-C5-알케닐옥시, C3-C5-알키닐옥시, 하이드록시, 아세톡시, 니트로, 아미노, 카복실 또는 실포 그룹이고, 보호된 옥심 그룹은 syn-형태로 존재한다.
  2. 제1항에 있어서, R1이 아세톡시메틸, 프로피오닐옥시메틸, 이소프로피오닐옥시메틸, N-부티릴옥시메틸, 이소부티릴옥시케닐, 2,2-디메틸프로피오닐옥시메틸, 이소발레릴옥시메틸, 1-아세톡시-1-에틸, 1-아세톡시-1-프로필, 2,2-디메틸프로피오닐옥시-1-에틸, 1-메톡시카보닐옥시-1-에틸, 1-에톡시카보닐옥시-1-에틸, 1-이소프로폭시카보닐옥시에틸 또는 메톡시카보닐옥시메틸이고, R2가 C(C6H5)3, 테트라하이드로피라닐 또는 2-메톡시-2-프로필이며, R3이 수소, 메틸, 에틸, 프로필, 메톡시, 에톡시, 프로폭시, 이소프로폭시 또는 염소이고, X가 Ck, Br, HSO4, CH2SO3, C2H5SO3, C6H5SO2, p-CH3-C6H4-SO3또는 p-Cl-C3H4-SO3인 방법.
  3. 제1항 또는 제2항에 있어서, 일반식(Ⅳ)의 화합물과 무기산 또는 지방족 또는 방향족 설폰산의 반응에서 HCl, HBr, H2SO4, 메탄설폰산, 에탄설폰산, 벤젠설폰산, p-플루엔설폰산 또는 2,4-디클로로벤젠설폰산이 사용되는 방법.
  4. 제1항 내지 제3항 중의 어느 한 항에 있어서, R1이 (R)- 또는 (S)-형태의 2,2-디메틸프로피오닐옥시-1-에틸인 방법.
  5. 제4항에 있어서, R1이 (S)-형태의 2,2-디메틸프로피오닐옥시-1-에틸인 방법.
  6. 일반식(Ⅱ＇)의 화합물.
    상기식에서, R2는 C(C6H5)이다.
  7. 일반식(Ⅱ＇)의 화합물.
    상기식에서, R2는이다.
  8. 에틸2-아미노티아졸-4-일-2-하이드록시이미노 아세테이트를 실온에서 불활성 용매 중에서 트리페닐 메틸 클로라이드 및 칼륨 3급-부틸레이트와 반응시키고, 형성된 에틸에스테르를 가수분해한 다음, 수독된 조악한 산을 20 내지 70℃의 온도에서 N,N-디메틸아세트아미드로 처리함을 포함하여, 제6항에서 청구한 일반식(Ⅱ")의 화합물을 제조하는 방법.
  9. R2가 C(C6H5)3인 일반식(Ⅳ)의 화합물을 제조하기 위한, 제6항에서 청구한 일반식(II″)의 화합물의 용도.
  10. R2는인 일반식(Ⅳ)의 화합물을 제조하기 위한, 제7항에서 청구한 일반식(Ⅱ")의 화합물의 용도.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019930001929A 1992-02-14 1993-02-12 세펨 프로드럭(prodrug) 에스테르의 제조방법 KR100265191B1 (ko)

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HU219587B (hu) 2001-05-28
US5637721A (en) 1997-06-10
HUT64350A (en) 1993-12-28
EP0555769B1 (de) 1999-09-15
TW212181B (ko) 1993-09-01
DE59309776D1 (de) 1999-10-21
CA2089441A1 (en) 1993-08-15
DK0555769T3 (da) 2000-03-20
CA2089441C (en) 2004-01-20
HU9300374D0 (en) 1993-04-28
US5589594A (en) 1996-12-31
FI930604A0 (fi) 1993-02-11
ES2137201T3 (es) 1999-12-16
EP0555769A3 (en) 1993-11-24
FI109027B (fi) 2002-05-15
GR3032076T3 (en) 2000-03-31
KR100265191B1 (ko) 2000-09-15
FI930604A (fi) 1993-08-15
JPH069650A (ja) 1994-01-18
JP3426629B2 (ja) 2003-07-14
EP0555769A2 (de) 1993-08-18
ATE184609T1 (de) 1999-10-15

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