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US4162360A Expired / Lapsed US ⏱️ 0.0 years remaining

3-Carbamoyloxymethyl-7-substituted oximino acetamido cephalosporanic acid derivatives

Assignee: Glaxo Laboratories Ltd
•
Filing: 1977-09-13
•
Granted: 1979-07-24
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Expires: 1997-09-13
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Abstract

Abstract 3-Carbamoyloxymethyl and 3-N-methylcarbamoyloxymethyl cephalosporin antibiotics in which the 7β-acylamido group has the structure ##STR1## where R is thienyl, furyl or phenyl; R a is C 1-4 alkyl, C 2-4 alkenyl, C 3-7 cycloalkyl or phenyl, and R b is hydrogen, carboxy, C 2 -C 5 carbalkoxy or any of the groups designated for R a , or R a and R b together with the carbon atom to which they are attached form a C 3-7 cycloalkylidene or cycloalkenylidene group; exhibit broad spectrum antibiotic activity characterized by particularly high activity against gram negative microorganisms, including those which produce β-lactamases. The compounds, which are syn isomers or exist as mixtures of syn and anti isomers containing at least 90% of the syn isomer, have particularly high in vitro activity against strains of Escherichia coli, Haemophilus influenzae and Proteus organisms; and also shown unusually high activity against Pseudomonas organisms.

Inventors

  • 👤 Janice Bradshaw
  • 👤 Martin C. Cook
  • 👤 Gordon I. Gregory

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 16:00
CPC Classifications
C; C07; C07D; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/24; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/54

Claims Analysis

Total Claims: 6
Claim 1
Independent Claim 54 words
A cephalosporin antibiotic of the formula ##STR24## wherein R is thienyl, furyl or phenyl; R a is methyl, ethyl, propyl, isopropyl, butyl, allyl, cyclohexyl or phenyl; R b is hydrogen, methyl, ethyl, propyl, isopropyl, butyl, allyl, cyclohexyl or phenyl; R 1 is hydrogen or methyl; or a physiologically acceptable salt, ester, or 1-oxide thereof.
Claim 2
Dependent Claim 54 words
A cephalosporin antibiotic of the formula ##STR24## wherein R is thienyl, furyl or phenyl; R a is methyl, ethyl, propyl, isopropyl, butyl, allyl, cyclohexyl or phenyl; R b is hydrogen, methyl, ethyl, propyl, isopropyl, butyl, allyl, cyclohexyl or phenyl; R 1 is hydrogen or methyl; or a physiologically acceptable salt, ester, or 1-oxide thereof.
Claim 3
Dependent Claim 47 words
A cephalosporin antibiotic of the formula ##STR25## wherein R is thienyl or furyl; R c is methyl, ethyl, propyl, allyl or phenyl; R d is hydrogen, methyl, ethyl, propyl, allyl or phenyl; and R 1 is hydrogen or methyl; or a physiologically acceptable salt or 1-oxide thereof.
Claim 4
Dependent Claim 47 words
A cephalosporin antibiotic of the formula ##STR25## wherein R is thienyl or furyl; R c is methyl, ethyl, propyl, allyl or phenyl; R d is hydrogen, methyl, ethyl, propyl, allyl or phenyl; and R 1 is hydrogen or methyl; or a physiologically acceptable salt or 1-oxide thereof.
Claim 5
Dependent Claim 11 words
The compound of claim 1 which is (6R,7R)-3-carbamoyloxymethyl-7-[2-(2-carboxyprop-2-yloxyimino)-2-(fur-2-yl)acetamido]ceph-3-em-4-carboxylic acid (syn isomer).
Claim 6
Dependent Claim 11 words
The compound of claim 1 which is (6R,7R)-3-carbamoyloxymethyl-7-[(2-(2-carboxyprop-2-yloxyimino)-2-phenylacetamido]ceph-3-em-4-carboxylic acid (syn isomer).

References Cited (Backward Citations)

US4095021A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1982-07-23 1983-01-22 1983-07-24 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-07-23 1987-01-22 1987-07-24 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1990-07-23 1991-01-22 1991-07-24 $7700.00 Window Closed / Lapsed

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