FR2373548A1 - NEW CEPHALOSPORIN DERIVATIVES WITH A WIDE-SPECTRUM OF ANTIBIOTIC ACTIVITY, THEIR METHOD OF PREPARATION AND THEIR THERAPEUTIC APPLICATION - Google Patents

NEW CEPHALOSPORIN DERIVATIVES WITH A WIDE-SPECTRUM OF ANTIBIOTIC ACTIVITY, THEIR METHOD OF PREPARATION AND THEIR THERAPEUTIC APPLICATION

Info

Publication number
FR2373548A1
FR2373548A1 FR7736153A FR7736153A FR2373548A1 FR 2373548 A1 FR2373548 A1 FR 2373548A1 FR 7736153 A FR7736153 A FR 7736153A FR 7736153 A FR7736153 A FR 7736153A FR 2373548 A1 FR2373548 A1 FR 2373548A1
Authority
FR
France
Prior art keywords
compounds
carboxylic acid
preparation
spectrum
group
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.)
Granted
Application number
FR7736153A
Other languages
French (fr)
Other versions
FR2373548B1 (en
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.)
Laboratoire Glaxo Wellcome SA
Glaxo Laboratories Ltd
Original Assignee
Laboratoires Glaxo SA
Glaxo Laboratories 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
Priority claimed from GB4996076A external-priority patent/GB1597359A/en
Application filed by Laboratoires Glaxo SA, Glaxo Laboratories Ltd filed Critical Laboratoires Glaxo SA
Publication of FR2373548A1 publication Critical patent/FR2373548A1/en
Application granted granted Critical
Publication of FR2373548B1 publication Critical patent/FR2373548B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/54—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
    • 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)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Communicable Diseases (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Oncology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Cephalosporin Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The compounds correspond to the formula: in which R denotes phenyl, thienyl or furyl, and Y denotes a group S(O)nR<1>, OR<3>, OCOR<4> or OCOAR<5>, and R<1>, R<3>, R<4>, R <8 > , A, n and the other symbols have the meanings given in Claim 1. The preparation is effected by reacting a 3-Ymethyl-7-aminoceph-2- or 3-em-4-carboxylic acid, whose carboxyl group can be blocked, or a corresponding salt or N-silyl derivative, with a carboxylic acid corresponding to the left hand part of the above formula, or with an acylating agent derived from this carboxylic acid, after which there is at most elimination of a carboxyl-blocking group. If the product is not obtained as a pure syn isomer, or with a content of at least 75 % thereof, an isomeric separation follows. In addition, the carboxylic acids can be esterified, 3-acyloxymethyl compounds can be deacylated to give 3-hydroxymethyl compounds, and 3-hydroxymethyl compounds can be acylated or carbamoylated. The compounds are antibiotics possessing a broad spectrum of activity; they are resistant to beta -lactamase and active, inter alia, against certain Enterobacteriaceae.
FR7736153A 1976-11-30 1977-11-30 NEW CEPHALOSPORIN DERIVATIVES WITH A WIDE-SPECTRUM OF ANTIBIOTIC ACTIVITY, THEIR METHOD OF PREPARATION AND THEIR THERAPEUTIC APPLICATION Granted FR2373548A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB4996076A GB1597359A (en) 1976-11-30 1976-11-30 7-(a-oxyimino-acetamido)-cephalosporin derivatives
GB4996176 1976-11-30

Publications (2)

Publication Number Publication Date
FR2373548A1 true FR2373548A1 (en) 1978-07-07
FR2373548B1 FR2373548B1 (en) 1981-09-11

Family

ID=26266572

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7736153A Granted FR2373548A1 (en) 1976-11-30 1977-11-30 NEW CEPHALOSPORIN DERIVATIVES WITH A WIDE-SPECTRUM OF ANTIBIOTIC ACTIVITY, THEIR METHOD OF PREPARATION AND THEIR THERAPEUTIC APPLICATION

Country Status (5)

Country Link
JP (1) JPS5387391A (en)
CH (1) CH637140A5 (en)
DE (1) DE2753220A1 (en)
FR (1) FR2373548A1 (en)
NL (1) NL7713136A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2432521A1 (en) * 1978-03-31 1980-02-29 Roussel Uclaf NOVEL O-SUBSTITUTED OXIMES DERIVED FROM 7-AMINO THIAZOLYL ACETAMIDO CEPHALOSPORANIC ACID, THEIR PREPARATION PROCESS AND THEIR USE AS MEDICAMENTS

Also Published As

Publication number Publication date
CH637140A5 (en) 1983-07-15
NL7713136A (en) 1978-06-01
FR2373548B1 (en) 1981-09-11
DE2753220A1 (en) 1978-06-01
JPS5387391A (en) 1978-08-01

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Legal Events

Date Code Title Description
ST Notification of lapse