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Improvements in or relating to cephalosporin antibiotics

Assignee: Glaxo Laboratories Ltd
•
Filing: 1974-12-16
•
Granted: 1977-04-26
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Expires: 1994-12-16
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Abstract

Abstract Cephalosporin antibiotics of formula ##STR1## (where R is 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 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; m and n are each 0 or 1 such that the sum of m and n is 0 or 1; and P is hydrogen or halogen) and their non-toxic derivatives 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; compounds wherein at least one of R a and R b is other than hydrogen have also shown unusually high activity against Pseudomonas organisms. Important compounds of the above type include those in which the 7β-acylamido group is a syn-2-carboxymethoxy-2-(fur-2-yl)acetamido, syn-2-(2-carboxyprop-2-yloxyimino)-2-(fur-2-yl)acetamido or syn-2-(1-carboxycyclopent-1-yloxyimino)-2-(fur-2-yl)acetamido group.

Inventors

  • 👤 John Derek Cocker
  • 👤 Derek Ronald Sutherland

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 12:39
CPC Classifications
C; C07; C07D; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/24; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/52

Claims Analysis

Total Claims: 9
Claim 1
Independent Claim 106 words
A compound selected from the group consisting of a cephalosporin antibiotic of the formula: ##STR14## wherein R is thienyl or furyl; R a and R b are each hydrogen, C 1-4 alkyl, C 2-4 alkenyl, C 3-7 cycloalkyl, phenyl, naphthyl, thienyl, furyl, carboxy, C 2-5 alkoxycarbonyl 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; m and n are each 0 or 1 such that the sum of m and n is 0 or 1; and P is hydrogen, or the physiologically acceptable salts, esters, 1-oxides and solvates thereof.
Claim 2
Dependent Claim 106 words
A compound selected from the group consisting of a cephalosporin antibiotic of the formula: ##STR14## wherein R is thienyl or furyl; R a and R b are each hydrogen, C 1-4 alkyl, C 2-4 alkenyl, C 3-7 cycloalkyl, phenyl, naphthyl, thienyl, furyl, carboxy, C 2-5 alkoxycarbonyl 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; m and n are each 0 or 1 such that the sum of m and n is 0 or 1; and P is hydrogen, or the physiologically acceptable salts, esters, 1-oxides and solvates thereof.
Claim 3
Dependent Claim 12 words
The compound of claim 1 which is (6R,7R)-7-[2-(2-carboxyprop-2-yloxyimino)-2-(fur-2-yl) acetamido]ceph-3-em-4-carboxylic acid (syn isomer).
Claim 4
Dependent Claim 12 words
The compound of claim 1 which is (6R,7R)-7-[2-(1-carboxycyclopent-1-yloxyimino)-2-(fur-2-yl) acetamido]ceph-3-em-4-carboxylic acid (syn isomer).
Claim 5
Dependent Claim 12 words
The compound of claim 1 which is (6R,7R)-7-[2-carboxymethoxyimino-2-(fur-2-yl) acetamido]ceph-3-em-4-carboxylic acid (syn isomer).
Claim 6
Dependent Claim 19 words
A compound according to claim 1 which is a sodium or potassium salt of a compound of formula I.
Claim 7
Dependent Claim 102 words
A compound of formula: ##STR15## wherein R is thienyl or furyl; R a and R b are each hydrogen, C 1-4 alkyl, C 2-4 alkenyl, C 3-7 cycloalkyl, phenyl, naphthyl, thienyl, furyl, carboxy, C 2-5 alkoxycarbonyl, 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; m and n are each 0 or 1 such that the sum of m and n is 0 or 1; R 2 is a blocked carboxy group; and P is hydrogen, or physiologically acceptable salts, esters, 1-oxides and solvates thereof.
Claim 8
Dependent Claim 102 words
A compound of formula: ##STR15## wherein R is thienyl or furyl; R a and R b are each hydrogen, C 1-4 alkyl, C 2-4 alkenyl, C 3-7 cycloalkyl, phenyl, naphthyl, thienyl, furyl, carboxy, C 2-5 alkoxycarbonyl, 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; m and n are each 0 or 1 such that the sum of m and n is 0 or 1; R 2 is a blocked carboxy group; and P is hydrogen, or physiologically acceptable salts, esters, 1-oxides and solvates thereof.
Claim 9
Dependent Claim 26 words
The compound of claim 1 which is the syn isomer or a mixture of syn and anti isomers containing at least 90% of the syn isomer.

References Cited (Backward Citations)

US3546219A Cited
US3573294A Cited
DE2204060A1 Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-04-25 1980-10-25 1981-04-26 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-04-25 1984-10-25 1985-04-26 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-04-25 1988-10-25 1989-04-26 $7700.00 Window Closed / Lapsed

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