US4165430A
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Cephalosporins having a 7-carboxy substituted α-etherified oximinoarylacetamido) group
Assignee: Glaxo Laboratories Ltd
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Filing: 1976-06-15
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Granted: 1979-08-21
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Expires: 1996-06-15
Abstract
Abstract Cephalosporin antibiotics having the formula: ##STR1## (where R is thienyl, furyl or phenyl; R a is hydrogen, C 1-4 alkyl, C 2-4 alkenyl, C 3-7 cycloalkyl or phenyl, and R b is hydrogen, C 1-4 alkyl, C 2-4 alkenyl, C 3-7 cycloalkyl, phenyl, carboxy or C 2-5 alkoxycarbonyl, 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: and Y is the residue of a nitrogen nucleophile and their physiologically acceptable 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; and 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
2026-11-06 01:45
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/54; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/24
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
196 words
A compound selected from the group consisting of a cephalosporin antibiotic of the formula: ##STR51## wherein R is thienyl or furyl; R a is hydrogen, methyl, ethyl, propyl, isopropyl, butyl, allyl, cyclohexyl or phenyl; R b is hydrogen, carboxy, C 2 -C 5 alkoxycarbonyl, methyl, ethyl, propyl, isopropyl, butyl, allyl, cyclohexyl or phenyl; or R a and R b together with the carbon atom to which they are attached form a C 3-7 cycloalkylidene group; Y is the residue of a nitrogen nucleophile which is a tri(C 1-6 alkyl) amine, or a heterocyclic tertiary amine which is a pyridine, pyrimidine, pyridazine, pyrazine, pyrazole, imidazole, triazole, thiazole, benzotriazole or purine, which may be substituted by a C 1-6 alkyl, phenyl, naphthyl, phenyl C 1-6 alkyl, (C 1-6 alkoxy) methyl, (C 2-7 alkanoyloxy)methyl, formyl, C 2-7 alkanoyl, C 2-7 alkanoyloxy, carboxy, C 2-7 alkoxycarbonyl, carboxy (C 1-6 alkyl), sulpho, C 1-6 alkoxy, phenoxy, phenyl C 1-6 alkoxy, C 1-6 alkylthio, phenylthio, phenyl C 1-6 alkylthio, cyano, hydroxy, carbamoyl, N-(C 1-6 alkyl) carbamoyl, N,N-di(C 1-6 alkyl) carbamoyl, N-(hydroxy C 1-6 alkyl)carbamoyl or carbamoyl C 1-6 alkyl group; or azido, and a physiologically acceptable salt, ester or a 1-oxide thereof.
Claim 2
Dependent Claim
196 words
A compound selected from the group consisting of a cephalosporin antibiotic of the formula: ##STR51## wherein R is thienyl or furyl; R a is hydrogen, methyl, ethyl, propyl, isopropyl, butyl, allyl, cyclohexyl or phenyl; R b is hydrogen, carboxy, C 2 -C 5 alkoxycarbonyl, methyl, ethyl, propyl, isopropyl, butyl, allyl, cyclohexyl or phenyl; or R a and R b together with the carbon atom to which they are attached form a C 3-7 cycloalkylidene group; Y is the residue of a nitrogen nucleophile which is a tri(C 1-6 alkyl) amine, or a heterocyclic tertiary amine which is a pyridine, pyrimidine, pyridazine, pyrazine, pyrazole, imidazole, triazole, thiazole, benzotriazole or purine, which may be substituted by a C 1-6 alkyl, phenyl, naphthyl, phenyl C 1-6 alkyl, (C 1-6 alkoxy) methyl, (C 2-7 alkanoyloxy)methyl, formyl, C 2-7 alkanoyl, C 2-7 alkanoyloxy, carboxy, C 2-7 alkoxycarbonyl, carboxy (C 1-6 alkyl), sulpho, C 1-6 alkoxy, phenoxy, phenyl C 1-6 alkoxy, C 1-6 alkylthio, phenylthio, phenyl C 1-6 alkylthio, cyano, hydroxy, carbamoyl, N-(C 1-6 alkyl) carbamoyl, N,N-di(C 1-6 alkyl) carbamoyl, N-(hydroxy C 1-6 alkyl)carbamoyl or carbamoyl C 1-6 alkyl group; or azido, and a physiologically acceptable salt, ester or a 1-oxide thereof.
Claim 3
Dependent Claim
12 words
The compound of claim 1 which is (6R,7R)-3-azidomethyl-7-[2-carboxymethyloxyimino-2-(fur-2-yl) acetamido]ceph-3-em-4-carboxylic acid (syn isomer).
Claim 4
Dependent Claim
10 words
The compound of claim 1 which is (6R,7R)-7-[2-carboxymethoxyimino-2-(fur-2-yl)acetamido]-3-pyridiniummethyl-ceph-3-em-4-carboxylate (syn isomer).
Claim 5
Dependent Claim
11 words
The compound of claim 1 which is (6R,7R)-7-[2-carboxyprop-2-yloxyimino-2-(fur-2-yl)-acetamido]-3-pyridiniummethyl-ceph-3-em-4-carboxylic acid (syn isomer).
Claim 6
Dependent Claim
11 words
The compound of claim 1 which is sodium (6R,7R)-7-[2-(carboxyprop-2-yloxyimino)-2-(fur-2-yl)-acetamido]-3-pyridiniummethylceph-3-em-4-carboxylate (syn isomer).
Claim 7
Dependent Claim
10 words
The compound of claim 1 which is (6R,7R)-3-[(4-carbamoylpyridinium)methyl]-7-[2-carboxyprop-2-yloxyimino-2-(fur-2-yl)acetamido]ceph-3-em-4-carboxylate (syn isomer).
Claim 8
Dependent Claim
10 words
The compound of claim 1 which is (6R,7R)-3-[(3-carboxymethylpyridinium)methyl]-7-[2-carboxyprop-2-yloxyimino-2-(fur-2-yl)acetamido]ceph-3-em-4-carboxylate (syn isomer).
Claim 9
Dependent Claim
10 words
The compound of claim 1 which is (6R,7R)-7-[2-cyclopent-1-yloxyimino-2-(fur-2-yl)acetamido]-3-pyridiniummethylceph-3-em-4-carboxylate (syn isomer).
Claim 10
Dependent Claim
10 words
The compound of claim 1 which is (6R,7R)-7-[2-cyclobut-1-yloxyimino-2-(fur-2-yl)acetamido]-3-pyridiniummethylceph-3-em-4-carboxylate (syn isomer).
Claim 11
Dependent Claim
11 words
The compound of claim 1 which is (6R,7R)-7-[2-carboxyprop-2-yloxyimino)-2-(fur-2-yl)acetamido]-3-pyridaziniummethylceph-3-em-4-carboxylic acid (syn isomer).
Claim 12
Dependent Claim
11 words
The compound of claim 1 which is (6R,7R)-7-[2-carboxyprop-2-yloxyimino-2-(fur-2-yl)acetamido]-3-(thiazol-3-ylmethyl)ceph-3-em-4-carboxylic acid (syn isomer).
Claim 13
Dependent Claim
10 words
The compound of claim 1 which is (6R,7R)-3-[(3-carbamoylpyridinium)methyl]-7-[2-carboxyprop-2-yloxyimino-2-(fur-2-yl)acetamido]ceph-3-em-4-carboxylate (syn isomer).
Claim 14
Dependent Claim
10 words
The compound of claim 1 which is (6R,7R)-3-[(3-sulphopyridinium)methyl]-7-[2-carboxyprop-2-yloxyimino-2-(fur-2-yl)acetamido]ceph-3-em-4-carboxylate (syn isomer).
Claim 15
Dependent Claim
11 words
The compound of claim 1 which is (6R,7R)-3-(benzotriazol-1-ylmethyl)-7-[2-(2-carboxyprop-2-yloxyimino)-2-(fur-2-yl)acetamido]ceph-3-em-4-carboxylic acid (syn isomer).
Claim 16
Dependent Claim
114 words
A compound selected from the group consisting of a cephalosporin antibiotic of the formula ##STR52## wherein R is thienyl or furyl, R c is methyl, ethyl, propyl, allyl or phenyl and R d is hydrogen, carboxy, methyl, ethyl, propyl, allyl or phenyl or R c and R d together with the carbon atom to which they are attached form a cyclobutylidene, cyclopentylidene or cyclohexylidene group and W is selected from (i) the group -CH 2 G where G is the residue of a nitrogen nucleophile selected from compounds of the formula ##STR53## wherein R f is hydrogen, carbamoyl, carboxymethyl or sulpho, and pyridazine; and (ii) azidomethyl; and a physiologically acceptable salt or 1-oxide thereof.
Claim 17
Dependent Claim
114 words
A compound selected from the group consisting of a cephalosporin antibiotic of the formula ##STR52## wherein R is thienyl or furyl, R c is methyl, ethyl, propyl, allyl or phenyl and R d is hydrogen, carboxy, methyl, ethyl, propyl, allyl or phenyl or R c and R d together with the carbon atom to which they are attached form a cyclobutylidene, cyclopentylidene or cyclohexylidene group and W is selected from (i) the group -CH 2 G where G is the residue of a nitrogen nucleophile selected from compounds of the formula ##STR53## wherein R f is hydrogen, carbamoyl, carboxymethyl or sulpho, and pyridazine; and (ii) azidomethyl; and a physiologically acceptable salt or 1-oxide thereof.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-08-20 | 1983-02-19 | 1983-08-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-08-20 | 1987-02-19 | 1987-08-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-08-20 | 1991-02-19 | 1991-08-21 | $7700.00 | Window Closed / Lapsed |