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7 2-(Aminocarbonylalkoxyimino)acetamido! derivatives of cephalosporin

Assignee: Glaxo Laboratories Ltd
•
Filing: 1976-06-09
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Granted: 1978-02-14
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Expires: 1996-06-09
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Abstract

Abstract Cephalosporin antibiotics in which the 7β-acylamido group has the structure ##STR1## (WHERE R is phenyl, thienyl or furyl; R a and R b are each selected from hydrogen, C 1-4 alkyl, C 2-4 alkenyl, C 3-7 cycloalkyl, phenyl, naphthyl, thienyl, furyl, carboxy, C 2-5 alkoxycarbonyl, aminocarbonyl, N-substituted aminocarbonyl and cyano, 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; R c is hydrogen or C 1-4 alkyl; and m and n are each 0 or 1 such that the sum of m and n is 0 or 1) 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 good activity against Proteus organisms including indole positive strains and, especially when both R a and R b are other than hydrogen, against Pseudomonas organisms.

Inventors

  • 👤 Michael W. Foxton
  • 👤 Gordon I. Gregory
  • 👤 David M. Rogers

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-25 18:03
CPC Classifications
C; C07; C07D; C07D501/00; C07D501/14; C07D501/16; C07D501/20; A; A61; A61P; A61P31/00; A61P31/04; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/54; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/24

Claims Analysis

Total Claims: 7
Claim 1
Independent Claim 129 words
A compound selected from the group consisting of a cephalosporin antibiotic of the formula ##STR50## wherein R is phenyl, thienyl or furyl; R a and R b are each hydrogen, C 1-4 alkyl, C 2-4 alkenyl, C 3-7 cycloalkyl, carboxy, C 2-5 alkoxycarbonyl, aminocarbonyl, N-(C 1- C 4 alkyl)aminocarbonyl or cyano, 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; R c is hydrogen or C 1-4 alkyl; m and n are each 0 or 1 such that the sum of m and n is 0 or 1; A is >O, >S or >NH; and R 17 is hydrogen or C 1-7 alkyl and a physiologically acceptable salt, metabolically labile ester pr 1-oxide thereof.
Claim 2
Dependent Claim 129 words
A compound selected from the group consisting of a cephalosporin antibiotic of the formula ##STR50## wherein R is phenyl, thienyl or furyl; R a and R b are each hydrogen, C 1-4 alkyl, C 2-4 alkenyl, C 3-7 cycloalkyl, carboxy, C 2-5 alkoxycarbonyl, aminocarbonyl, N-(C 1- C 4 alkyl)aminocarbonyl or cyano, 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; R c is hydrogen or C 1-4 alkyl; m and n are each 0 or 1 such that the sum of m and n is 0 or 1; A is >O, >S or >NH; and R 17 is hydrogen or C 1-7 alkyl and a physiologically acceptable salt, metabolically labile ester pr 1-oxide thereof.
Claim 3
Dependent Claim 13 words
The compound of claim 1 which is (6R, 7R)-7- 2-aminocarbonylmethoxyimino-2-(fur-2-yl)-acetamido!-3-carbamoyloxymethyl-ceph-3-em-4-carboxylic acid (syn isomer).
Claim 4
Dependent Claim 12 words
The compound of claim 1 is (6R, 7R)-7- 2-(2-aminocarbonylprop-2-yloxyimino)-2-(fur-2-yl)acetamido!-3-carbamoyloxymethylceph-3-em-4-carboxylic acid (syn isomer).
Claim 5
Dependent Claim 13 words
The compound of claim 1 which is pivaloyloxymethyl (6R, 7R)-7- 2-aminocarbonylmethoxyimino-2-(fur-2-yl)acetamido!-3-carbamoyloxymethylceph-3-em-4-carboxylate (syn isomer).
Claim 6
Dependent Claim 13 words
The compound of claim 1 which is (6R, 7R)-7- 2-(1-aminocarbonylcyclobut-1-yloxyimino)-2-(fur-2-yl)-acetamido!-3-carbamoyloxymethyl-ceph-3-em-4-carboxylic acid (syn isomer).
Claim 7
Dependent Claim 29 words
A compound according to claim 1 wherein R a and R b together with the carbon atom to which they are attached form a cyclobutylidene, cyclopentylidene or cyclohexylidene group.

References Cited (Backward Citations)

DE2204060A1 Cited
DE2223375A1 Cited
US3971778A Cited
DE2262500A1 Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-02-13 1981-08-15 1982-02-14 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-02-13 1985-08-15 1986-02-14 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-02-13 1989-08-15 1990-02-14 $7700.00 Window Closed / Lapsed

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