US3971778A
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Cephalosporins having (α-etherified oximino)acylamido groups at the 7-position
Assignee: Glaxo Laboratories Ltd
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Filing: 1972-11-07
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Granted: 1976-07-27
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Expires: 1992-11-07
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 ##EQU1## 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 or 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
2026-10-25 21:57
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/30; C07D207/32; C07D207/325; 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
Claims Analysis
Total Claims: 36
Claim 1
Independent Claim
147 words
A compound selected from the group consisting of a highly active cephalosporin antibiotic highly stable to β-lactamases of the formula ##SPC24## wherein R u is thienyl or furyl; R b is lower alkyl; lower alkyl substituted by amino, bromo or lower alkoxy; or cycloalkyl of 3-7 carbon atoms; and P is vinyl or a group of the formula --CH 2 Y in which Y is --SW where W is 5-methyl-1,3,4-thiadiazol-2-yl, 1-methyltetrazol-5-yl, 1-ethyltetrazol-5-yl, 5-phenyl-1,3,4-oxadiazol-2-yl or nitrobenzothiazolyl; alkylthio of 1-4 carbon atoms; lower alkylcarbonylthio; a group of the formula --O.CO.R 9 where R 9 is alkyl or alkenyl of up to 4 carbon atoms, phenyl or cycloalkyl of 3-6 carbon atoms; or azido, 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
147 words
A compound selected from the group consisting of a highly active cephalosporin antibiotic highly stable to β-lactamases of the formula ##SPC24## wherein R u is thienyl or furyl; R b is lower alkyl; lower alkyl substituted by amino, bromo or lower alkoxy; or cycloalkyl of 3-7 carbon atoms; and P is vinyl or a group of the formula --CH 2 Y in which Y is --SW where W is 5-methyl-1,3,4-thiadiazol-2-yl, 1-methyltetrazol-5-yl, 1-ethyltetrazol-5-yl, 5-phenyl-1,3,4-oxadiazol-2-yl or nitrobenzothiazolyl; alkylthio of 1-4 carbon atoms; lower alkylcarbonylthio; a group of the formula --O.CO.R 9 where R 9 is alkyl or alkenyl of up to 4 carbon atoms, phenyl or cycloalkyl of 3-6 carbon atoms; or azido, 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
79 words
A compound selected from the group consisting of a highly active cephalosporin antibiotic highly stable to β-lactamases of the formula ##SPC25## wherein R x is thienyl or furyl and R c is an alkyl group containing 2-4 carbon atoms or cyclopentyl, 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 4
Dependent Claim
79 words
A compound selected from the group consisting of a highly active cephalosporin antibiotic highly stable to β-lactamases of the formula ##SPC25## wherein R x is thienyl or furyl and R c is an alkyl group containing 2-4 carbon atoms or cyclopentyl, 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 5
Dependent Claim
115 words
A compound selected from the group consisting of a highly active cephalosporin antibiotic highly stable to β-lactamases of the formula ##SPC26## wherein R x is thienyl or furyl and R b is lower alkyl; lower alkyl substituted by amino, bromo or lower alkoxy; or cycloalkyl of 3-7 carbon atoms; and V is an alkylthio group of 1-4 carbon atoms or a group of formula --O.CO.R 9 where R 9 is alkyl or alkenyl of 2-4 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 6
Dependent Claim
115 words
A compound selected from the group consisting of a highly active cephalosporin antibiotic highly stable to β-lactamases of the formula ##SPC26## wherein R x is thienyl or furyl and R b is lower alkyl; lower alkyl substituted by amino, bromo or lower alkoxy; or cycloalkyl of 3-7 carbon atoms; and V is an alkylthio group of 1-4 carbon atoms or a group of formula --O.CO.R 9 where R 9 is alkyl or alkenyl of 2-4 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 7
Dependent Claim
114 words
A compound selected from the group consisting of a highly active cephalosporin antibiotic highly stable to β-lactamases of the formula ##SPC27## wherein R x is thienyl or furyl, 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 wherein R x is thienyl or furyl and R c is an alkyl group containing 2-4 carbon atoms or cylopentyl, 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 8
Dependent Claim
114 words
A compound selected from the group consisting of a highly active cephalosporin antibiotic highly stable to β-lactamases of the formula ##SPC27## wherein R x is thienyl or furyl, 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 wherein R x is thienyl or furyl and R c is an alkyl group containing 2-4 carbon atoms or cylopentyl, 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 9
Dependent Claim
11 words
The compound of claim 1 which is 3-acetoxymethyl-7β-[2-methoxyimino-2-(thien-2-yl)acetamido]-ceph3-em-4l -carboxylic acid (syn-isomer).
Claim 10
Dependent Claim
11 words
The compound of claim 1 which is 3-acetozymethyl 7β-[2-ethoxyimino-2-(thien-2-yl)acetamido]-ceph-3-em-4-carboxylic acid (syn-isomer).
Claim 11
Dependent Claim
10 words
The compound of claim 1 which is 3-acetoxymethyl-7β-[2-n-butoxyimino-2-(thien-2-yl)acetamido]-ceph-3-em-4-carboxylic acid (syn-isomer).
Claim 12
Dependent Claim
10 words
The compound of claim 1 which is 3-acetoxymethyl-7β-[2-t-butoxyimino-2-(thien-2-yl)acetamido]-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-methoxymethoxyimino-2-(thien-2-yl)acetamido]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-(1-ethoyethoyimino)-2-(thien-2-yl)acetamido]ceph-3-em-4-carboxylic acid (syn-isomer).
Claim 15
Dependent Claim
11 words
The compound of claim 1 which is 3-acetoxymethyl-7β-[2-(2-bromoethoyimino)-2-(hien-2-yl) acetamido]-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-(2-aminoethoxyimino)-2-(thien-2-yl)acetamido]ceph-3-em-4-carboxylic acid (syn-isomer).
Claim 17
Dependent Claim
10 words
The compound of claim 1 which is 3-azidomethyl-7β-[2-ethoxyimino-2(thien-2-yl)acetamido]-ceph-3-em-4-carboxylic acid (syn-isomer).
Claim 18
Dependent Claim
10 words
The compound of claim 1 which is 3-azidomethyl-7β-[2-t-butoxyimino-2(thien-2-yl)acetamido]ceph-3-em-4-carboxylic acid (syn-isomer).
Claim 19
Dependent Claim
10 words
The compound of claim 1 which is 3-actoxymethyl-7β-[2-methoxyimino-2-(fur-2-yl)acetamido]-ceph-3-em-4-carboxylic acid (syn-isomer).
Claim 20
Dependent Claim
10 words
The compound of claim 1 which is 3-acetoxymethyl-7β-[2-t-butoxyimino-2-(fur-2-yl)acetamido]-ceph-3-em-4-carboxylic acid (syn-isomer).
Claim 21
Dependent Claim
10 words
The compound of claim 1 which is 3-azidomethyl-7β-[2-methoxyimino-2-(thien-2-yl)acetamido]ceph-3-em-4-carboxylic acid (syn-isomer).
Claim 22
Dependent Claim
10 words
The compound of claim 1 which is 7β-[2-t-butoxyimino-2-(thien-2-yl)acetamido]-3-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethylceph-3-em-4-carboxylic acid (syn-isomer).
Claim 23
Dependent Claim
10 words
The compound of claim 1 which is 3-acetoxymethyl-7β-[2-ethoxyimino-2-(fur-2-yl)acetamido]-ceph-3-em-4-carboxylic acid (syn-isomer).
Claim 24
Dependent Claim
10 words
The compound of claim 1 which is 3-acetoxymethyl-7β-[2-propoxyimino-2-(thien-2-yl)acetamido]3-em-4-carboxylic acid (syn-isomer).
Claim 25
Dependent Claim
10 words
The compound of claim 1 which is 3-acetoxymethyl-7β-[2-ethoxyimino-2-(thien-3-yl)acetamido]-ceph-3-em-4-carboxylic acid (syn-isomer).
Claim 26
Dependent Claim
11 words
The compound of claim 1 which is 3-acetoxymethyl-7β-[2-cyclopentyloxyimino-2-(2-furyl)actamido]ceph-3-em-4-carboxylic acid (syn isomer).
Claim 27
Dependent Claim
11 words
The compound of claim 1 which is 3-acetoxymethyl-7β-[2-cyclopentyloxyimino-2-(2-thienyl)acetamido]ceph-3-em-4-carboxylic acid (syn isomer).
Claim 28
Dependent Claim
11 words
The compound of claim 1 which is 3(1-methyltetrazol-5-yl)thiomethyl-7β-[2-t-butoxyimino-2-(2-thienyl) acetamido]ceph-3-em-4-carboxylic acid (syn-isomer)
Claim 29
Dependent Claim
11 words
The compound of claim 1 which is 3-(1-methyltetrazol-5-yl)thiomethyl-7β-[2-t-butoxyimino-2-(2-furyl)-acetamido]ceph-3-em-4-carboxylic acid (syn isomer)
Claim 30
Dependent Claim
12 words
The compound of claim 1 which is 3-(1-methyltetrazol-5-yl)thiomethyl 7β-[2-cyclopentyloxyimino-2-(2-thienyl)acetamido]ceph-β-em-4-carboxyic acid (syn isomer)
Claim 31
Dependent Claim
11 words
The compound of claim 1 which is 3-(1-methyltetrazol-5-yl)thiomethyl-7β-[2-cyclopentyloxyimino-2-(2-furyl)-acetamido]ceph-β-em-4-carboxylic acid (syn isomer)
Claim 32
Dependent Claim
11 words
The compound of claim 1 which is 3-(1-ethyltetrazol-5-yl)thiomethyl-7β-[2-t-butoxyimino-2-(2-thienyl)acetamido]ceph-3-em-4-carboxylic acid (syn isomer).
Claim 33
Dependent Claim
11 words
The compound of claim 1 which is 7β-[2-t-butoxyimino-2-(2-thienyl)acetamido]-3-(6-nitrobenzothiazol-2-yl)thiomethylceph-3-em-4-carboxylic acid (syn isomer)
Claim 34
Dependent Claim
11 words
The compound of claim 1 wich is 7β-[2-cyclopentyloxyimine-2-(2-furyl)acetamido]-3-(6-nitrobenzothiazol-2-yl)thiomethylceph-3-em-4-carboxylic acid (syn isomer).
Claim 35
Dependent Claim
11 words
The compound of claim 1 which is 7β-2-t-butoxyimino-2-(thien-2-yl)acetamido]-3-(5-phenyl-1,3,4-oxadiazol-2-ylthiomethyl) ceph-3-em-4-carboxylic acid (synisomer).
Claim 36
Dependent Claim
11 words
The compound of claim 1 which is 7β[2-t-butoxyimino-2-(thien-2-yl)acetamido]-3-crotonoyloxymethylceph-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) | 1979-07-27 | 1980-01-26 | 1980-07-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-07-27 | 1984-01-26 | 1984-07-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-07-27 | 1988-01-26 | 1988-07-27 | $7700.00 | Window Closed / Lapsed |