KR940009190A - 7β- [2- (2-aminothiazol-4-yl)-(Z) -2-methoxyiminoacetamido] -3-[(1,2,3-thiadiazol-5-yl) Method for preparing thiomethyl] -3-cepem-4-carboxylic acid - Google Patents

7β- [2- (2-aminothiazol-4-yl)-(Z) -2-methoxyiminoacetamido] -3-[(1,2,3-thiadiazol-5-yl) Method for preparing thiomethyl] -3-cepem-4-carboxylic acid Download PDF

Info

Publication number
KR940009190A
KR940009190A KR1019920019378A KR920019378A KR940009190A KR 940009190 A KR940009190 A KR 940009190A KR 1019920019378 A KR1019920019378 A KR 1019920019378A KR 920019378 A KR920019378 A KR 920019378A KR 940009190 A KR940009190 A KR 940009190A
Authority
KR
South Korea
Prior art keywords
reaction
cepem
methoxyiminoacetamido
aminothiazol
carboxylic acid
Prior art date
Application number
KR1019920019378A
Other languages
Korean (ko)
Other versions
KR950013568B1 (en
Inventor
안승호
이광혁
김영진
윤명식
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
Application filed by 김정순, 제일제당 주식회사 filed Critical 김정순
Priority to KR1019920019378A priority Critical patent/KR950013568B1/en
Publication of KR940009190A publication Critical patent/KR940009190A/en
Application granted granted Critical
Publication of KR950013568B1 publication Critical patent/KR950013568B1/en

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
    • C07D501/14—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
    • C07D501/36—Methylene radicals, substituted by sulfur atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

본 발명은 반응물에 트리페닐포스핀(Ph3P)과 헥사클로로에탄(C2Cl6)을 반응시켜 아실옥시포스포니움 클로라이드 유도체를 생성시키고, 이를 유리시킴이 없이 실릴화 반응 및 아실화 반응을 행하여 7-β-[2-(2-아미노티아졸-4-일)-(Z)-2-메톡시이미노아세트아미도]-3-[(1,2,3-티아디아졸-5-일)티오메틸]-3-세펨-4-카르복실산의 제조방법을 제공하였다.The present invention reacts the reaction product with triphenylphosphine (Ph 3 P) and hexachloroethane (C 2 Cl 6 ) to produce an acyloxy phosphonium chloride derivative, without the silylation reaction and acylation reaction 7-β- [2- (2-aminothiazol-4-yl)-(Z) -2-methoxyiminoacetamido] -3-[(1,2,3-thiadiazole- 5-yl) thiomethyl] -3-cepem-4-carboxylic acid is provided.

본 발명의 제조방법은 반응온도가 실온근처에서 진행되고 반응완료 후 쉽게 목적물을 분리해 낼 수 있으며, 높은 수율 및 고품질의 생성물??르 얻을 수 있는 장점이 있다.The production method of the present invention has the advantage that the reaction temperature proceeds to near room temperature and can easily separate the target product after the reaction is completed, high yield and high quality products.

Description

7β-[2-(2-아미노티아졸-4-일)-(Z)-2-메톡시이미노아세트아미도]-3-[(1,2,3-티아디아졸-5-일)티오메틸]-3-세펨-4-카르복실산의 제조방법7β- [2- (2-aminothiazol-4-yl)-(Z) -2-methoxyiminoacetamido] -3-[(1,2,3-thiadiazol-5-yl) Method for preparing thiomethyl] -3-cepem-4-carboxylic acid

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (5)

트리페닐포스핀(Ph3P)과 헥사클로로에탄(C2Cl6)을 유기용매 중에서 구조식(III)의 화합물과 반응시켜 얻은 구조식(IV)의 아실옥시포스포니움클로라이드 유도체를 유리시키기 않고, 구조식(II)의 화합물을 유기용매 중에서 염기 존재하 또는 염기 존재 없이 실릴화제 시약을 사용하여 실릴화 반응시켜 얻은 화합물과 아실화 반응시킴을 특징으로 하는 다음 구조식(I)의 7β-[2-(2-아미노티아졸-4-일)-(Z)-2-메톡시이미노아세트아미도]-3-세펨-4-카르복실산의 제조방법.Without liberating the acyloxyphosphonium chloride derivative of formula (IV) obtained by reacting triphenylphosphine (Ph 3 P) and hexachloroethane (C 2 Cl 6 ) with a compound of formula (III) in an organic solvent, The compound of formula (II) is acylated with a compound obtained by silylation reaction using a silylating agent reagent with or without base in an organic solvent, wherein 7β- [2- ( 2-Aminothiazol-4-yl)-(Z) -2-methoxyiminoacetamido] -3-cepem-4-carboxylic acid. 제1항에 있어서, 아실옥시포스포니움 클로라이드의 생성 및 실릴화 반응의 유기용매는 디클로로메탄, 아세토니트릴, 테트라하이드로푸란으로 구성된 군으로 부터 선택됨을 특징으로 하는 제조방법.The process according to claim 1, wherein the organic solvent of the production and silylation reaction of acyloxyphosphonium chloride is selected from the group consisting of dichloromethane, acetonitrile and tetrahydrofuran. 제1항에 있어서, 실릴화 시약은 디클로디메틸실란, 클로로트리메틸 실란, 헥사메틸디실라잔, N, O-비스-트리메틸실릴아세트아미드, N,N-비스-트리메틸실릴우레아로 구성된 군으로 부터 선택됨을 특징으로 하는 제조방법.The method of claim 1, wherein the silylation reagent is from the group consisting of dichlorodimethylsilane, chlorotrimethyl silane, hexamethyldisilazane, N, O-bis-trimethylsilylacetamide, N, N-bis-trimethylsilylurea Method of manufacturing characterized in that the selected. 제1항에 있어서, 염기는 트리에틸아민, 피리딘, N,N-디메틸아닐린으로 구성된 군으로 부터 선택됨을 특징으로 하는 제조방법.The process according to claim 1, wherein the base is selected from the group consisting of triethylamine, pyridine, N, N-dimethylaniline. 제1항에 있어서, 아실화 반응은 -5~40℃온도에서 1~3시간 진행시킴을 특징으로 하는 제조방법.The method of claim 1, wherein the acylation reaction is performed at a temperature of −5 to 40 ° C. for 1 to 3 hours. ※참고사항:최초출원 내용에 의하여 공개하는 것임.※ Note: This is to be disclosed based on the first application.
KR1019920019378A 1992-10-21 1992-10-21 Process for the preparation of 7ñô-£2-(2-aminothiazol-4-yl|-(z)-2-methoxy iminoacetamido|-3-{(1,2,3-thiadiazol-5-yl)thiomethyl|-3-cephem-4-carboxylic acid KR950013568B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1019920019378A KR950013568B1 (en) 1992-10-21 1992-10-21 Process for the preparation of 7ñô-£2-(2-aminothiazol-4-yl|-(z)-2-methoxy iminoacetamido|-3-{(1,2,3-thiadiazol-5-yl)thiomethyl|-3-cephem-4-carboxylic acid

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR1019920019378A KR950013568B1 (en) 1992-10-21 1992-10-21 Process for the preparation of 7ñô-£2-(2-aminothiazol-4-yl|-(z)-2-methoxy iminoacetamido|-3-{(1,2,3-thiadiazol-5-yl)thiomethyl|-3-cephem-4-carboxylic acid

Publications (2)

Publication Number Publication Date
KR940009190A true KR940009190A (en) 1994-05-20
KR950013568B1 KR950013568B1 (en) 1995-11-09

Family

ID=19341516

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019920019378A KR950013568B1 (en) 1992-10-21 1992-10-21 Process for the preparation of 7ñô-£2-(2-aminothiazol-4-yl|-(z)-2-methoxy iminoacetamido|-3-{(1,2,3-thiadiazol-5-yl)thiomethyl|-3-cephem-4-carboxylic acid

Country Status (1)

Country Link
KR (1) KR950013568B1 (en)

Also Published As

Publication number Publication date
KR950013568B1 (en) 1995-11-09

Similar Documents

Publication Publication Date Title
KR950018013A (en) Method for producing cefem derivatives
EP0091141B1 (en) Process for the preparation of thioethers
KR930010043A (en) Method for producing cefem derivatives
KR940009190A (en) 7β- [2- (2-aminothiazol-4-yl)-(Z) -2-methoxyiminoacetamido] -3-[(1,2,3-thiadiazol-5-yl) Method for preparing thiomethyl] -3-cepem-4-carboxylic acid
KR940009191A (en) 7- [α- (Z) -methoxyimino-α- (2-aminothiazol-4-yl) acetamido] -3-[(5-carboxymethyl-4-methylthiazol-2-yl ) How to prepare thiomethyl] -3-cepem-4-carboxylic acid
JPS5936914B2 (en) Cephalosporin analogs
US4422971A (en) Process for the preparation of 6-aminopenicillanic acid-1,1-dioxide
EP0117872B1 (en) Process for preparing cephalosporin compounds
KR100192616B1 (en) A process for the preparation of 7-[1-(1h)-tetrazolylacetamido]-3-[2-(5-methyl-1,3,4-thiadiazolyl)thimmethyl]-3-cephem-4-carboxylic acid
KR960037686A (en) (6R, 7R) -7-[(Z) -2- (2-aminothiazol-4-yl) -2-trityloxyiminoacetamido] -3- [2- (5-methyl-1 Method for preparing 3,4-thiadiazolyl) thiomethyl] -3-cef-4-carboxylic acid
KR950011448A (en) Process for preparing 7β-[(Z) -2- (2-amino-4-thiazolyl) -2- (carboxymethoxyimino) acetamido] -3-vinyl-3-cefe-4-carboxylic acid
KR950013571B1 (en) Process for the preparation o(6r,7r)-7-£(z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)ace tamido|-3-(1-pyridiniommethyl)ceph-3-em-4-carboxylate 2 hydrochloride salt
KR950013567B1 (en) Process for the preparation of cephem derivatives
KR0139590B1 (en) Process for the preparation of sepem derivatives
KR100472048B1 (en) Novel method for producing Aztreonam
CA1067892A (en) Iodo compounds
JP3655939B2 (en) Novel process for the preparation of 13-alkyl milbemycin intermediates
KR0184037B1 (en) Method of preparing cephem derivatives
KR790001045B1 (en) Process for the conversion of 6-aminopenicillanic acid(6-apa) into 7-aminodesacetokyciphalos poranic acid(7-adca)
GB2001985A (en) Penam and cephem production
US4835267A (en) Process for the preparation of cephalosporin derivatives
KR100254312B1 (en) Process for producing 3-norcephem compounds
SE7908285L (en) IMPROVEMENTS OF OR WITH REGARD TO THE PREPARATION OF SEMI-SYNTHETIC PENICILLIN ANTIBIOTICS
KR950023646A (en) (6R, 7R) -7-[(Z) -2 (2-aminopiazol-4-yl) -2- (2-t-butoxycarbonylprop-2-oxyimino) acetamido]- Method for preparing 3- (1-pyridiniummethyl) -3-cepem-4-carboxylate
GB1312030A (en) Penicillin compounds and a method of synthesising same

Legal Events

Date Code Title Description
A201 Request for examination
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