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US4092477A
Expired / Lapsed
US
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7β-[2-Etherified oximino-2-(phenyl- or naphthylacetamido)] cephalosporins
Assignee: Glaxo Laboratories Ltd
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Filing: 1977-01-26
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Granted: 1978-05-30
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Expires: 1997-01-26
Abstract
Abstract The invention provides novel antibiotic compounds which are 7 beta -acylamidoceph-3-em-4-carboxylic acids, and non-toxic derivatives thereof characterized in that the acylamido group has the structure <IMAGE> where R is a hydrogen atom or an organic group and Ra is an etherifying monovalent organic group linked to the oxygen atom through a carbon atom. The compounds are syn isomers or exist as mixtures containing at least 75% of the syn isomer. These antibiotic compounds possess high antibacterial activity against a range of gram positive and gram negative organisms coupled with particularly high stability to beta -lactamases produced by various gram negative organisms. The invention is also concerned with the administration of the compounds.
Inventors
- 👤 Martin Christopher Cook
- 👤 Gordon Ian Gregory
- 👤 Janice Bradshaw
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 23:22
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/30; C07D207/32; C07D207/325; C07C; C07C271/00; C07C271/06; C07C271/08; C07C271/10; C07C271/14; C07D209/00; C07D209/02; C07D209/44; C07D209/48; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/54; C07D213/55; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/40; C07D307/42; C07D307/54; C07D307/77; C07D307/78; C07D307/79; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/14; C07D333/16; C07D333/24; C07D333/50; C07D333/52; C07D333/54; C07D333/60; C07D499/00
Claims Analysis
Total Claims: 5
Claim 1
Independent Claim
143 words
A compound selected from the group consisting of a highly active cephalosporin antibiotic highly stable to β-lactamases, having the formula ##STR149## wherein R u is phenyl or naphthyl or each of these groups substituted by a chloro, bromo, iodo, fluoro, hydroxy, lower alkyl, nitro, amino, loweralkylamino, diloweralkylamino, lower alkanoyl, lower alkanoylamino, lower alkoxy, lower alkylthio or carbamoyl; R b is lower alkyl or cycloalkyl of 3-7 carbon atoms; Y is a group of formula -SW where W is thiadiazolyl, 5-methyl-1,3,4-thiadiazol-2-yl, diazolyl, triazolyl, tetrazolyl, 1-methyltetrazol-5-yl, thiazolyl, thiatriazolyl, oxazolyl, oxadiazolyl, 2-phenyl-1,3,4-oxadiazol-5-yl, benzimidazolyl, benzoxazolyl, triazolopyridyl, benzothiazolyl, nitrobenzothiazolyl, purinyl, pyridyl, pyrimidyl or an alkyl group of 1-4 carbon atoms, said cephalosporin antibiotic being in the form of a syn isomer free of the corresponding anti isomer to the extent of at least 75% based on the total weight of said antibiotic; and a physiologically acceptable salt thereof.
Claim 2
Dependent Claim
143 words
A compound selected from the group consisting of a highly active cephalosporin antibiotic highly stable to β-lactamases, having the formula ##STR149## wherein R u is phenyl or naphthyl or each of these groups substituted by a chloro, bromo, iodo, fluoro, hydroxy, lower alkyl, nitro, amino, loweralkylamino, diloweralkylamino, lower alkanoyl, lower alkanoylamino, lower alkoxy, lower alkylthio or carbamoyl; R b is lower alkyl or cycloalkyl of 3-7 carbon atoms; Y is a group of formula -SW where W is thiadiazolyl, 5-methyl-1,3,4-thiadiazol-2-yl, diazolyl, triazolyl, tetrazolyl, 1-methyltetrazol-5-yl, thiazolyl, thiatriazolyl, oxazolyl, oxadiazolyl, 2-phenyl-1,3,4-oxadiazol-5-yl, benzimidazolyl, benzoxazolyl, triazolopyridyl, benzothiazolyl, nitrobenzothiazolyl, purinyl, pyridyl, pyrimidyl or an alkyl group of 1-4 carbon atoms, said cephalosporin antibiotic being in the form of a syn isomer free of the corresponding anti isomer to the extent of at least 75% based on the total weight of said antibiotic; and a physiologically acceptable salt thereof.
Claim 3
Dependent Claim
11 words
The compound of claim 1 which is 3-methylthiomethyl-7β-(2-methoxyimino-2-phenylacetamido)-ceph-3-em-4-carboxylic acid (syn isomer).
Claim 4
Dependent Claim
12 words
The compound of claim 1 which is 7β-(2-ethoxyimino-2-phenylacetamido)-3-(5-methyl-1,3-4-thiadiazol-2-yl) thiomethyl-ceph-3-em-4-carboxylic acid (syn isomer).
Claim 5
Dependent Claim
11 words
The compound of claim 1 which is 7β-(2-ethoxyimino-2-phenylacetamido)-3-(1-methyltetrazol-5-yl)thiomethylceph-3-em-4-carboxylic acid (syn isomer).
References Cited (Backward Citations)
US4024133A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-05-29 | 1981-11-28 | 1982-05-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-05-29 | 1985-11-28 | 1986-05-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-05-29 | 1989-11-28 | 1990-05-30 | $7700.00 | Window Closed / Lapsed |