KR930010043A - 세펨 유도체의 제조방법 - Google Patents

세펨 유도체의 제조방법 Download PDF

Info

Publication number
KR930010043A
KR930010043A KR1019910020505A KR910020505A KR930010043A KR 930010043 A KR930010043 A KR 930010043A KR 1019910020505 A KR1019910020505 A KR 1019910020505A KR 910020505 A KR910020505 A KR 910020505A KR 930010043 A KR930010043 A KR 930010043A
Authority
KR
South Korea
Prior art keywords
methyl
organic solvent
base
derivative
formula
Prior art date
Application number
KR1019910020505A
Other languages
English (en)
Other versions
KR950014571B1 (ko
Inventor
이광혁
고동현
김영진
장명식
Original Assignee
김정순
제일제당 주식회사
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to KR1019910020505A priority Critical patent/KR950014571B1/ko
Application filed by 김정순, 제일제당 주식회사 filed Critical 김정순
Priority to EP92919241A priority patent/EP0613480B1/en
Priority to NL9220025A priority patent/NL9220025A/nl
Priority to PCT/KR1992/000041 priority patent/WO1993010123A1/en
Priority to CH2208/93A priority patent/CH684091A5/de
Priority to DE4293959T priority patent/DE4293959T1/de
Priority to DE4293959A priority patent/DE4293959C2/de
Priority to AT0903092A priority patent/AT403048B/de
Priority to GB9409758A priority patent/GB2275927B/en
Priority to JP5509158A priority patent/JPH0811755B2/ja
Priority to US07/959,359 priority patent/US5317099A/en
Publication of KR930010043A publication Critical patent/KR930010043A/ko
Priority to ES09350013A priority patent/ES2070101B1/es
Priority to DK056694A priority patent/DK56694A/da
Priority to SE9401706A priority patent/SE505050C2/sv
Application granted granted Critical
Publication of KR950014571B1 publication Critical patent/KR950014571B1/ko

Links

Classifications

    • 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
    • C07D501/02—Preparation
    • C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
    • C07D501/06—Acylation of 7-aminocephalosporanic acid
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oncology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Communicable Diseases (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

본 발명은 항생 물질로 유용한 다음 구조식(I)의 β-락탐 유도체의 새로운 제조방법에 관한 것이다.
위 구조식에서 R1은 수소 또는 금속염을 의미하여 R2는 수소, 아세톡시 메틸, (2,5-디히드로-2-메틸-6-히드록시-5-옥소-as-트리아진-3-일)티오메틸 또는 (1-메틸-1H-테트라졸-5-일)티오메틸을 의미한다. 본 발명은 트리페닐포스핀(Ph3P)과 헥사클로로에탄(C2Cl6)를 유기용매중에서 [2-아미노-α-(메톡시이미노)-티아졸-4-일]초산과 반응시켜 얻는 구조식(IV)의 화합물인 아실옥시포스포니움클로라이드와 7-ACA 및 그 유도체(V)를 유기용매 중에서 염기존재하 또는 염기 존재 없이 실릴화제 시약을 사용하여 실릴화 반응시켜 얻는 화합물과의 아실화 반응을 특징으로 하는 다음 구조식(I)의 세펨 유도체의 제조방법에 있다.

Description

세펨 유도체의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (6)

  1. 트리페닐포스핀(Ph3P)과 헥사클로로에탄(C2Cl6)또는 시염화탄소(CCl4)를 유기용매 중에서 구조식(Ⅲ)의 유기산과 반응시켜 얻은 구조식(Ⅳ)의 아실옥소포스포니움 클로라이드 화합물을 얻고, 실릴화제 시약을 사용하여 7-ACA 및 그 유도체(V)를 유기용매 중에서 염기존재 하 또는 염기 존재 없이 실릴화 반응시킨 후 화합물(Ⅳ)와 아실화 반응시킴을 특징으로 하는 다음 구조식(I)의 세펨 유도체의 제조방법.
    상기 각 구조식에서, R2는 수소, 아세톡시메틸, (1-메틸-1H-테트라졸-5-일) 티오메틸 또는 (2,5-디히드로-2-메틸-6-히드록시-5-옥소-as-트리아진-3-일)티오 메틸을 의미하며, R1은 수소 또는 금속염을 의미한다.
  2. 제1항에 있어서, 유기용매는 디클로로메탄, 아세토니트릴, 테트라하이드로푸란으로 구성된 군으로부터 선택됨을 특징으로 하는 제조방법.
  3. 제1항에 있어서, 실릴화제 시약은 디클로로디메틸실란, 클로로트리메틸실란, 헥사메틸디실라잔, N,O-비스-트리메틸-실릴아세트아미드로 구성된 군으로부터 선택됨을 특징으로 하는 제조방법.
  4. 제1항에 있어서, 염기는 트리에틸아민, 피리딘, N,N-디메틸아닐린으로 구성된 군으로부터 선택됨을 특징으로 하는 제조방법.
  5. 제1항에 있어서, 아실화 반응은 -5∼40℃온도에서 1-3시간 진행되는 것을 특징으로 하는 제조방법.
  6. 제1항에 있어서, 트리페닐포스핀, 헥사클로로에탄 또는 사염화탄소는 구조식(Ⅲ)의 유기산에 대하여 1.0∼1.3당량으로 사용됨을 특징으로 하는 제조방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019910020505A 1991-11-18 1991-11-18 세펨 유도체의 제조방법 KR950014571B1 (ko)

Priority Applications (14)

Application Number Priority Date Filing Date Title
KR1019910020505A KR950014571B1 (ko) 1991-11-18 1991-11-18 세펨 유도체의 제조방법
GB9409758A GB2275927B (en) 1991-11-18 1992-09-04 Process for the preparation of cephem derivatives
PCT/KR1992/000041 WO1993010123A1 (en) 1991-11-18 1992-09-04 Process for the preparation of cephem derivatives
CH2208/93A CH684091A5 (de) 1991-11-18 1992-09-04 Verfahren für die Herstellung von Cephem-Derivaten (Cephalosporine).
DE4293959T DE4293959T1 (de) 1991-11-18 1992-09-04 Verfahren zur Herstellung von Cephem Derivaten
DE4293959A DE4293959C2 (de) 1991-11-18 1992-09-04 Verfahren zur Herstellung von Cephem Derivaten
EP92919241A EP0613480B1 (en) 1991-11-18 1992-09-04 Process for the preparation of cephem derivatives
NL9220025A NL9220025A (nl) 1991-11-18 1992-09-04 Werkwijze voor het bereiden van cephemderivaten.
JP5509158A JPH0811755B2 (ja) 1991-11-18 1992-09-04 セフェム誘導体の製造方法
AT0903092A AT403048B (de) 1991-11-18 1992-09-04 Verfahren zur herstellung von cephem-derivaten
US07/959,359 US5317099A (en) 1991-11-18 1992-10-13 Process for the preparation of cephem derivatives
ES09350013A ES2070101B1 (es) 1991-11-18 1993-07-16 Procedimiento para la preparacion de derivados de cefem.
DK056694A DK56694A (da) 1991-11-18 1994-05-18 Fremgangsmåde til fremstilling af cephemderivater
SE9401706A SE505050C2 (sv) 1991-11-18 1994-05-18 Process för framställning av cephemderivat

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR1019910020505A KR950014571B1 (ko) 1991-11-18 1991-11-18 세펨 유도체의 제조방법

Publications (2)

Publication Number Publication Date
KR930010043A true KR930010043A (ko) 1993-06-21
KR950014571B1 KR950014571B1 (ko) 1995-12-08

Family

ID=19322986

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019910020505A KR950014571B1 (ko) 1991-11-18 1991-11-18 세펨 유도체의 제조방법

Country Status (13)

Country Link
US (1) US5317099A (ko)
EP (1) EP0613480B1 (ko)
JP (1) JPH0811755B2 (ko)
KR (1) KR950014571B1 (ko)
AT (1) AT403048B (ko)
CH (1) CH684091A5 (ko)
DE (2) DE4293959C2 (ko)
DK (1) DK56694A (ko)
ES (1) ES2070101B1 (ko)
GB (1) GB2275927B (ko)
NL (1) NL9220025A (ko)
SE (1) SE505050C2 (ko)
WO (1) WO1993010123A1 (ko)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5402609A (en) * 1992-08-13 1995-04-04 Kelley, Jr.; Michael L. Concrete building block system
TW369530B (en) * 1993-06-10 1999-09-11 Lucky Ltd Process for preparing cephalosporin compounds from reactive organic acid derivatives
KR100197788B1 (ko) * 1995-06-30 1999-06-15 김충환 세펨 유도체의 제조방법
IN181459B (ko) * 1995-12-26 1998-06-20 Lupin Lab Ltd
WO2005076694A2 (en) * 2004-01-16 2005-08-25 Wockhardt Limited Improved process for the production of cefotaxime sodium
CN108383857B (zh) * 2018-05-04 2021-02-05 山东四环药业股份有限公司 一种盐酸头孢甲肟的制备方法

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2760123C2 (de) * 1976-01-23 1986-04-30 Roussel-Uclaf, Paris 7-Aminothiazolyl-syn-oxyiminoacetamidocephalosporansäuren, ihre Herstellung und sie enthaltende pharmazeutische Zusammensetzungen
US4196205A (en) * 1976-01-23 1980-04-01 Roussel Uclaf 3-Acetoxymethyl-7-(iminoacetamido)-cephalosporanic acid derivatives
US4166115A (en) * 1976-04-12 1979-08-28 Fujisawa Pharmaceutical Co., Ltd. Syn 7-oxoimino substituted derivatives of cephalosporanic acid
US4304770A (en) * 1976-04-12 1981-12-08 Fujisawa Pharmaceutical Co., Ltd. Syn-isomer of 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and processes for the preparation thereof
US4331664A (en) * 1976-04-12 1982-05-25 Fujisawa Pharmaceutical Co., Ltd. Syn isomer of 7-[2-cyclo(lower) alkoxyimino-2-(2-amino-or substituted aminothiazol-4-yl)acetamido]-3-lower alkanoyloxymethyl or heterocyclicthiomethyl-3-cephem-4-carboxylic acid compounds
DE2760484C2 (ko) * 1976-04-14 1992-12-03 Takeda Chemical Industries, Ltd., Osaka, Jp
US4370326A (en) * 1977-09-13 1983-01-25 Fujisawa Pharmaceutical Co., Ltd. Cephem compounds and composition
DE2758000A1 (de) * 1977-12-24 1979-07-05 Hoechst Ag Verfahren zur herstellung von penicillinen und cephalosporinen
CH641468A5 (de) * 1978-05-30 1984-02-29 Hoffmann La Roche Cephemderivate.
MC1259A1 (fr) * 1978-05-30 1980-01-14 Hoffmann La Roche Derives acyles
GB2025933B (en) * 1978-06-13 1982-10-27 Fujisawa Pharmaceutical Co Cephem and cepham compounds
FR2462439A1 (fr) * 1979-07-26 1981-02-13 Roussel Uclaf Nouveau procede de preparation de produits derives de l'acide 7-/(2-aryl) 2-hydroxyimino acetamido/cephalosporanique
CY1365A (en) * 1980-03-28 1987-08-07 Biochemie Gmbh New process for the production of cephalosporin antibiotics, and novel intermediates used in such process and their production
KR870001332B1 (ko) * 1984-09-27 1987-07-18 한미약품공업 주식회사 세펨 유도체의 간단한 제조방법
ATE155469T1 (de) * 1988-03-16 1997-08-15 Eisai Co Ltd Verfahren zur herstellung von cephemderivaten
IT1234385B (it) * 1989-05-23 1992-05-18 Sbd Synthetic And Biolog Devel Procedimento migliorato per la produzione di una sostanza antibiotica appartenente al gruppo delle cefalosporine

Also Published As

Publication number Publication date
NL9220025A (nl) 1994-12-01
ATA903092A (de) 1997-03-15
SE9401706D0 (sv) 1994-05-18
US5317099A (en) 1994-05-31
JPH0811755B2 (ja) 1996-02-07
SE505050C2 (sv) 1997-06-16
WO1993010123A1 (en) 1993-05-27
CH684091A5 (de) 1994-07-15
EP0613480B1 (en) 1999-03-31
EP0613480A1 (en) 1994-09-07
DE4293959T1 (de) 1995-01-26
KR950014571B1 (ko) 1995-12-08
ES2070101A1 (es) 1995-05-16
GB2275927B (en) 1995-10-04
AT403048B (de) 1997-10-27
JPH07501072A (ja) 1995-02-02
GB2275927A (en) 1994-09-14
GB9409758D0 (en) 1994-07-20
SE9401706L (sv) 1994-07-07
ES2070101B1 (es) 1996-02-16
DK56694A (da) 1994-05-18
DE4293959C2 (de) 1996-08-29

Similar Documents

Publication Publication Date Title
KR970003125B1 (ko) α,β-불포화 케토락톤의 제조방법
KR930010043A (ko) 세펨 유도체의 제조방법
US4895941A (en) Process for preparing 2α-methyl-2β-(1,2,3-triazol-1-yl)methylpenam-3α-carboxylic acid derivatives
US4808712A (en) Process for preparing cephalosporin compounds
US4422971A (en) Process for the preparation of 6-aminopenicillanic acid-1,1-dioxide
US4379923A (en) Preparation of 7-acylamino-3-(thio-substituted)-methyl 3-cephem-4-carboxylic acid-1-oxide derivatives
KR950011448A (ko) 7β-[(Z)-2-(2-아미노-4-티아졸일)-2-(카르복시메톡시이미노)아세트아미도]-3-비닐-3-세펨-4-카르복실산의 제조방법
KR940009190A (ko) 7β-[2-(2-아미노티아졸-4-일)-(Z)-2-메톡시이미노아세트아미도] -3-[(1,2,3-티아디아졸-5-일)티오메틸]-3-세펨-4-카르복실산의 제조방법
KR950013569B1 (ko) 7-[α-(Z)-메톡시이미노-α-(2-아미노티아졸-4-일)아세트아미도]-3-[(5-카르복시메틸-4-메틸티아졸-2-일)티오메틸]-3-세펨-4-카르복실산의 제조방법
CA1067892A (en) Iodo compounds
KR790001045B1 (ko) 6-아미노페니실라닌산을 7-아미노데스아세톡시세팔로스포라닌산으로 전환시키는 방법
KR100192616B1 (ko) 7-[1-(1h)-테트라졸일아세트아미도]-3-[2-(5-메틸1,3,4-티아디아졸일)티오메틸]-3-세펨-4-카르복실산의 제조방법
KR940014412A (ko) (6r,7r)-7-[(z)-2-(2-아미노티아졸-4-일)-2-(2-카르복시프로프-2-옥시이미노)아세트아미도]-3-(1-피리디늄 메틸)세프-3-엠-4-카르복실레이트 이염산염의 제조방법
US4357275A (en) Novel oxazolinoazetidinones and process therefor
KR960037686A (ko) (6r,7r)-7-[(z)-2-(2-아미노티아졸-4-일)-2-트리틸옥시이미노아세트아미도]-3-[2-(5-메틸-1,3,4-티아디아졸일)티오메틸]-3-세펨-4-카르복실산의 제조방법
KR940011469A (ko) 세펨유도체의 제조방법
KR900003274B1 (ko) 티아졸 유도체의 제조방법
KR0139590B1 (ko) 세펨 유도체의 제조방법
SE7908285L (sv) Forbettringar vid eller med avseende pa framstellning av halvsyntetiska penicillinantibiotika
KR890009940A (ko) 실릴세팔로스포린 화합물 및 그 제조방법
KR950023646A (ko) (6R,7R)-7-[(Z)-2(2-아미노피아졸-4-일)-2-(2-t-부톡시카르보닐프로프-2-옥시이미노)아세트아미도]-3-(1-피리디늄메틸)-3-세펨-4-카르복실레이트의 제조방법
ES8302687A1 (es) "procedimiento para la preparacion de derivados de 2-oxa-biciclo (3.3.0) octano".
KR880003957A (ko) 세팔로스포린 유도체의 제조방법
KR950032214A (ko) 세펨 유도체의 제조방법
JPH0696553B2 (ja) 新規ｎ−フルオロエチルピリドチオン類化合物

Legal Events

Date Code Title Description
A201 Request for examination
E801 Decision on dismissal of amendment
E902 Notification of reason for refusal
E601 Decision to refuse application
J2X1 Appeal (before the patent court)

Free format text: APPEAL AGAINST DECISION TO DECLINE REFUSAL

G160 Decision to publish patent application
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
FPAY Annual fee payment

Payment date: 20050930

Year of fee payment: 11

LAPS Lapse due to unpaid annual fee