GB1414324A - Process for preparing 7-acylamino-3-substituted-3-cephem-4- carboxylic acid derivatives - Google Patents

Process for preparing 7-acylamino-3-substituted-3-cephem-4- carboxylic acid derivatives

Info

Publication number
GB1414324A
GB1414324A GB5894772A GB5894772A GB1414324A GB 1414324 A GB1414324 A GB 1414324A GB 5894772 A GB5894772 A GB 5894772A GB 5894772 A GB5894772 A GB 5894772A GB 1414324 A GB1414324 A GB 1414324A
Authority
GB
United Kingdom
Prior art keywords
cephalosporin
group
compounds
compound
reaction
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
GB5894772A
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.)
Fujisawa Pharmaceutical Co Ltd
Original Assignee
Fujisawa Pharmaceutical 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 Fujisawa Pharmaceutical Co Ltd filed Critical Fujisawa Pharmaceutical Co Ltd
Publication of GB1414324A publication Critical patent/GB1414324A/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
    • 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

Abstract

1414324 Cephalosporin compounds FUJISAWA PHARMACEUTICAL CO Ltd 20 Dec 1972 [23 Dec 1971] 58947/72 Heading C2C Cephalosporins having the general Formula (I) and salts thereof, wherein R 1 is a hydrogen atom, a substituted or unsubstituted heterocyclic-thio group or an alkylthio group, R 2 is an acyl group and R 4 is hydrogen or a residue of an ester are prepared by subjecting a cephalosporin C derivative of general Formula (II) or a salt thereof, wherein R 3 is an acyl group and R 1 and R 4 are as defined above, which compounds are said to be novel, to the following reactions: (i) reaction with a silylating agent, (ii) treatment of the resulting compound with an iminohalogenating agent, (iii) reaction of the resulting iminohalide with an imino-etherforming compound, (iv) acylation of the iminoether with an acylating agent providing the group R 2 , and (v) hydrolyzing the resulting compound to remove substituents other than R 2 from the 7-amino group. The starting cephalosporin C derivative (II) may be prepared by reacting cephalosporin C, optionally in the form of a cephalosporin C- containing fermentation broth, with an appropriate N-acylating agent (e.g. phenylisocyanate or benzoyl chloride giving respectively 7-[5-(N- phenylcarbamoylamino)adipoylamino - cephalosporanic acid and 7-[5-(N-benzoylamino)- adipoylamino-cephalosporanic acid) and then subjecting the N-acylated compound to a 3- position replacement reaction, e.g. to give the corresponding 3 - (5-methyl-1,3,4 - thiadiazol - 2-yl)-thiomethyl compounds.
GB5894772A 1971-12-23 1972-12-20 Process for preparing 7-acylamino-3-substituted-3-cephem-4- carboxylic acid derivatives Expired GB1414324A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP25177271 1971-12-23

Publications (1)

Publication Number Publication Date
GB1414324A true GB1414324A (en) 1975-11-19

Family

ID=17227685

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5894772A Expired GB1414324A (en) 1971-12-23 1972-12-20 Process for preparing 7-acylamino-3-substituted-3-cephem-4- carboxylic acid derivatives

Country Status (4)

Country Link
DK (1) DK154889C (en)
ES (1) ES410009A1 (en)
GB (1) GB1414324A (en)
SE (1) SE428693B (en)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1953861C2 (en) * 1969-10-25 1982-12-23 Fujisawa Pharmaceutical Co., Ltd., Osaka 7-tetrazolylacetamido-3-thiomethyl-3-cephem-4-carboxylic acids
BE758587A (en) * 1969-11-17 1971-05-06 Fujisawa Pharmaceutical Co PROCESS FOR THE PREPARATION OF 7-AMINOCEPHALOSPORANIC ACID DERIVATIVES AND NEW PRODUCTS THUS OBTAINED

Also Published As

Publication number Publication date
DK154889B (en) 1989-01-02
ES410009A1 (en) 1975-12-01
DK154889C (en) 1989-06-12
SE428693B (en) 1983-07-18

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PE20 Patent expired after termination of 20 years

Effective date: 19921218