GB1377376A - Process for producing cephalosporins - Google Patents

Process for producing cephalosporins

Info

Publication number
GB1377376A
GB1377376A GB5704671A GB5704671A GB1377376A GB 1377376 A GB1377376 A GB 1377376A GB 5704671 A GB5704671 A GB 5704671A GB 5704671 A GB5704671 A GB 5704671A GB 1377376 A GB1377376 A GB 1377376A
Authority
GB
United Kingdom
Prior art keywords
acid
formula
cephalosporins
aminophenylacetamido
aryloxy
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
GB5704671A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Toyama Chemical Co Ltd
Original Assignee
Toyama Chemical Co Ltd
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 Toyama Chemical Co Ltd filed Critical Toyama Chemical Co Ltd
Priority to GB5704671A priority Critical patent/GB1377376A/en
Publication of GB1377376A publication Critical patent/GB1377376A/en
Expired legal-status Critical Current

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
    • 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

Landscapes

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

Abstract

1377376 Preparation of cephalosporins TOYAMA CHEMICAL CO Ltd 8 Dec 1971 57046/71 Heading C2C [Also in Division C3] A process for the preparation of cephalosporins of Formula I: wherein R is hydrogen, acetoxy, alkoxy or S-R<SP>1</SP> (R<SP>1</SP> is alkyl, aryl or a heterocyclic group), R<SP>1</SP> and R<SP>2</SP> are hydrogen or an optionally substituted alkyl, aryl, aralkyl, aryloxy, cycloalkane or heterocyclic group, or R<SP>1</SP> and R<SP>2</SP> may jointly form a ring; R<SP>3</SP> is hydrogen, halogen, hydroxyl, amino, alkylamino, azido, alkyloxy, alkylthio, benzyloxycarbonyl, benzhydroxycarbonyl, # - haloethoxycarbonyl, #,#,# - trihaloethoxycarbonyl or an alkoxycarbonyl group and n is 0 or 1, comprises reacting 7-aminocephalosporanic acids of Formula II: with silyl halides of Formula III: in which R 4 and R 5 may be the same or different and may be alkyl, haloalkyl, aryl, aralkyl, alkoxy, haloalkoxy, alkyloxyalkyl, aryloxy, aralkyloxy or halogen, R 6 is alkyloxy, aryloxy, haloalkyloxy or aralkyloxy and X is halogen, in the presence of a tertiary amine to protect the carboxyl group of the 7-aminocephalosporanic acids by forming a mixed acid anhydride grouping, then reacting the product obtained in the presence of an acid binding agent with acylating derivatives of carboxylic acids of Formula IV: and then solvolysing the product to remove the protecting group. Examples of cephalosporins which may be prepared by this process include 7 - (2 - thienylacetamido) cephalosporanic acid, 7 - (α - aminophenylacetamido)- cephalosporanic acid, 7 - (α - aminophenylacetamido) - 3 - desacetoxy cephalosporanic acid, 7 - (α - aminophenylacetamido) - 3 - methoxymethyl - 3 - cephem - 4 - carboxylic acid, 7 - [1 - (1H) - tetrazolylacetamido]- 3 - [2 - 5- methyl - 1,3,4 - thiadiazolylthiomethyl]- 3- cephem - 4 - carboxylic acid and 7 - [α - amino- (p - hydroxyphenyl) - acetamido] - 3 - desacetoxy-cephalosporanic acid.
GB5704671A 1971-12-08 1971-12-08 Process for producing cephalosporins Expired GB1377376A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB5704671A GB1377376A (en) 1971-12-08 1971-12-08 Process for producing cephalosporins

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB5704671A GB1377376A (en) 1971-12-08 1971-12-08 Process for producing cephalosporins

Publications (1)

Publication Number Publication Date
GB1377376A true GB1377376A (en) 1974-12-11

Family

ID=10478215

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5704671A Expired GB1377376A (en) 1971-12-08 1971-12-08 Process for producing cephalosporins

Country Status (1)

Country Link
GB (1) GB1377376A (en)

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee