US4024137A
Expired / Lapsed
US
⏱️ 0.0 years remaining
7β-[2-Etherified oximino-2-(phenyl- or naphthylacetamido)] cephalosporins
Assignee: Glaxo Laboratories Ltd
•
Filing: 1975-06-16
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Granted: 1977-05-17
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Expires: 1995-06-16
Abstract
Abstract The invention provides novel antibiotic compounds which are 7β-acylamidoceph-3-em-4-carboxylic acids, and non-toxic derivatives thereof characterized in that the acylamido group has the structure ##STR1## WHERE R is a hydrogen atom or an organic group and R a 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 β-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
2026-10-30 04:52
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: 16
Claim 1
Independent Claim
125 words
A compound selected from the group consisting of a highly active cephalosporin antibiotic highly stable to β-lactamases, having the formula ##STR132## wherein R u is phenyl or naphthyl or each of these groups substituted by 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 containing 3-7 carbon atoms; and, R 9 is an alkyl or alkenyl group containing up to 4 carbon atoms, cyclopropyl, cyclopentyl, cyclohexyl, or phenyl, 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
125 words
A compound selected from the group consisting of a highly active cephalosporin antibiotic highly stable to β-lactamases, having the formula ##STR132## wherein R u is phenyl or naphthyl or each of these groups substituted by 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 containing 3-7 carbon atoms; and, R 9 is an alkyl or alkenyl group containing up to 4 carbon atoms, cyclopropyl, cyclopentyl, cyclohexyl, or phenyl, 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
12 words
A compound as claimed in claim 1 in which Y is acetoxy.
Claim 4
Dependent Claim
10 words
The compound of claim 1 which is 3-acetoxymethyl-7β-[2-methoxyimino-2-phenylacetamido]-ceph-3-em-4-carboxylic acid (syn-isomer).
Claim 5
Dependent Claim
10 words
The compound of claim 1 which is 3-acetoxymethyl-7β-[2-ethoxyimino-2-phenylacetamido]-ceph-3-em-4-carboxylic acid (syn-isomer).
Claim 6
Dependent Claim
10 words
The compound of claim 1 which is 3-acetoxymethyl-7β-[2-t-butoxyimino-2-phenylacetamido]-ceph-3-em-4-carboxylic acid (syn-isomer).
Claim 7
Dependent Claim
12 words
The compound of claim 1 which is 3-acetoxymethyl-7β-[2-methoxyimino-2-(naphth-1-yl) acetamido]-ceph-3-em-4-carboxylic acid (syn isomer).
Claim 8
Dependent Claim
10 words
The compound of claim 1 which is 3-acetoxymethyl-7β-[2-t-butoxyimino-2-(naphth-1-yl)acetamido]-ceph-3-em-4-carboxylic acid (syn-isomer).
Claim 9
Dependent Claim
11 words
The compound of claim 1 which is 3-cyclopropylcarbonyloxymethyl-7β-(2-ethoxyimino-2-phenylacetamido)-ceph-3-em-4-carboxylic acid (syn isomer).
Claim 10
Dependent Claim
11 words
The compound of claim 1 which is 3-isobutyryloxymethyl-7β-[2-methoxyimino-2-phenylacetamido]ceph-3-em-4-carboxylic acid (syn isomer).
Claim 11
Dependent Claim
10 words
The compound of claim 1 which is 3-benzoyloxymethyl-7β-[2-methoxyimino-2-phenylacetamido]ceph-3-em-4-carboxylic acid (syn-isomer).
Claim 12
Dependent Claim
10 words
The compound of claim 1 which is 3-crotonyloxymethyl-7β-[2-methoxyimino-2-phenylacetamido]ceph-3-em-4-carboxylic acid (syn-isomer).
Claim 13
Dependent Claim
10 words
The compound of claim 1 which is 3-acetoxymethyl-7β-[2-n-butoxyimino-2-phenylacetamido]-ceph-3-em-4-carboxylic acid (syn-isomer).
Claim 14
Dependent Claim
10 words
The compound of claim 1 which is 3-acetoxymethyl-7β-[2-isopropoxyimino-2-phenylacetamido]-ceph-3-em-4-carboxylic acid (syn-isomer).
Claim 15
Dependent Claim
10 words
The compounds of claim 1 which is 3-acetoxymethyl-7β-[2-n-propoxyimino-2-phenylacetamido]-ceph-3-em-4-carboxylic acid (syn-isomer).
Claim 16
Dependent Claim
10 words
The compound of claim 1 which is 3-acetoxymethyl-7β-(2-cyclopentyloxyimino-2-phenylacetamido)ceph-3-em-4-carboxylic acid (syn-isomer).
References Cited (Backward Citations)
US3546219A
Cited
US3573294A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-05-16 | 1980-11-15 | 1981-05-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-05-16 | 1984-11-15 | 1985-05-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-05-16 | 1988-11-15 | 1989-05-17 | $7700.00 | Window Closed / Lapsed |