US3974153A
Expired / Lapsed
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7-Hydrocarbonoxy imino-acetamido-3-carbamoyloxy methylceph-3-em-4 carboxylic acids
Assignee: Glaxo Laboratories Ltd
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Filing: 1974-08-13
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Granted: 1976-08-10
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Expires: 1994-08-13
Abstract
Abstract Cephalosporin antibiotics in which the 7β-acylamido group has the structure ##EQU1## where R 1 is a furyl, thienyl or phenyl group and R 2 is a C 1 -C 4 alkyl, C 3 C 7 cycloalkyl or phenyl group and in which the 3-position substituent is a carbamoyloxymethyl group possess a particularly valuable combination of properties, exhibiting high antibacterial activity against a broad range of gram positive and gram negative organisms, particularly high stability to β-lactamases produced by various organisms, and stability in vivo. The compounds are syn isomers or exist as mixtures of syn and anti isomers containing at least 90% of the syn isomer. Particularly important compounds of this type are (6R,7R)-3-carbamoyloxymethyl -7-[2-(fur-2-yl)-2-methoxyiminoacetamido]ceph-3-em-4-carboxylic acid (syn isomer) and its non-toxic derivatives, e.g. the sodium salt.
Inventors
- 👤 Martin Christopher Cook
- 👤 Gordon Ian Gregory
- 👤 Janice Bradshaw
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 02:32
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/40; C07D307/42; C07D307/54; C07D307/77; C07D307/78; C07D307/79; C07D501/00; C07D501/14; C07D501/16; C07D501/20; C07D501/24; C07D501/26
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
41 words
A compound selected from the group consisting of a cephalosprin antibiotic of the formula ##SPC6## wherein R 1 is furyl, thienyl, or phenyl; and R a is C 1-4 alkyl, C 3-7 cycloalkyl or phenyl; and a physiologically acceptable salt thereof.
Claim 2
Dependent Claim
41 words
A compound selected from the group consisting of a cephalosprin antibiotic of the formula ##SPC6## wherein R 1 is furyl, thienyl, or phenyl; and R a is C 1-4 alkyl, C 3-7 cycloalkyl or phenyl; and a physiologically acceptable salt thereof.
Claim 3
Dependent Claim
11 words
The compound of claim 1 which is (6R,7R)-3-carbamoyloxymethyl-7-[2-(fur-2-yl)-2-methoxyiminoacetamido]ceph-3-em-4-carboxylate acid (syn isomer).
Claim 4
Dependent Claim
11 words
The compound of claim 1 which is sodium (6R,7R)-3-carbamoyloxymethyl-7-[2-(fur-2-yl)-2-methoxyiminoacetamido]ceph-3-em-4-carboxylate (syn isomer).
Claim 5
Dependent Claim
84 words
The compound of claim 1 which is sodium (6R,7R)-3-carbamoyloxymethyl-7-[2-(fur-2-yl)-2-methoxyiminoacetamido]ceph-3-em-4-carboxylate (syn isomer) in crystalline form having the following characteristic X-ray powder pattern (d= d-spacing; I = intensity:d I d I______________________________________8.33 80 3.05 47.44 4 2.93 14 (broad)6.85 45 2.72 8 poorly re-6.38 5 2.69 10 solved5.86 4 2.57 95.36 4 2.47 64.82 100 2.40 104.56 35 2.35 104.36 6 2.26 44.19 40 2.20 33.95 26 2.11 8 (broad)3.82 24 2.04 33.62 28 1.94 43.47 28 1.89 53.32 10 1.82 6 (broad)3.19 10 1.77 2 .______________________________________
Claim 6
Dependent Claim
66 words
The compound of claim 1 which is sodium (6R,7R)-3-carbamoyloxymethyl-7-[2-(fur-2-yl)-2-methoxyiminoacetamido]ceph-3-em-4-carboxylate (syn isomer) in crystalline form having the following characteristic X-ray powder pattern (d = d-spacing; I = intensity: d I d I
______________________________________
8.78 60 3.49 14
7.81 9 3.07 6 (broad)
6.65 25 2.91 8
4.68 100 (broad) 2.77 6
4.45 10 2.32 3 (broad)
4.20 10 2.19 2
3.76 20 (broad) 2.08 2 .
______________________________________
Claim 7
Dependent Claim
76 words
The compound of claim 1 which is sodium (6R,7R)-3-carbamoyloxymethyl-7-[2-(fur-2-yl)-2-methoxyiminoacetamido]ceph-3-em-4-carboxylate (syn isomer) in crystalline form having the following characteristic X-ray powder pattern (d = d-spacing; I = intensity: d I d I
______________________________________
14.98 60 4.29 20
12.95 40 4.16 100
10.16 20 3.81 25 (broad)
8.23 45 3.60 20
7.52 5 3.47 5
6.61 65 3.32 10
6.08 3 3.26 30
5.57 20 3.13 17 (broad)
4.98 40 2.43 10
4.73 60 2.15 15 .
______________________________________
Claim 8
Dependent Claim
63 words
The compound of claim 1 which is sodium (6R,7R)-3-carbamoyloxymethyl-7-[2-(fur-2-yl)-2-methoxyiminoacetamido]ceph-3-em-4-carboxylate (syn isomer) in crystalline form having the following characteristic X-ray powder pattern (d = d-spacing; I = intensity: d I d I
______________________________________
8.85 70 3.75 35
7.80 6 3.10 1
7.15 25 2.93 4
6.01 20 2.76 12
5.06 18 2.62 1
4.65 100 2.41 2
4.30 25 2.30 3
4.01 25.
______________________________________
Claim 9
Dependent Claim
11 words
The compound of claim 1 which is (6R,7R)-3-carbamoyloxymethyl-7-[2-(fur-2-yl)-2-phenoxyiminoacetamido]ceph-3-em-4-carboxylic acid (syn isomer).
Claim 10
Dependent Claim
11 words
The compound of claim 1 which is (6R,7R)-3-carbamoyloxymethyl-7-[2-cyclopentyloxyimino-2-(fur-2-yl)acetamido]ceph-3-em-4-carboxylic acid (syn isomer).
Claim 11
Dependent Claim
11 words
A compound of claim 1 which is (6R,7R)-3-carbamoyloxymethyl-7-[2-methoxyimino-2-phenylacetamido]ceph-3-em-4-carboxylic acid (syn isomer).
Claim 12
Dependent Claim
11 words
A compound of claim 1 which is (6R,7R)-3-carbamoyloxymethyl-7-[2-ethoxyimino-2-phenylacetamido]ceph-3-em-4-carboxylic acid (syn isomer).
Claim 13
Dependent Claim
11 words
A compound of claim 1 which is (6R,7R)-3-carbamoyloxymethyl-7-[2-phenoxyimino-2-phenylacetamido]ceph-3-em-4-carboxylic acid (syn isomer).
Claim 14
Dependent Claim
11 words
The compound of claim 1 which is (6R,7R)-3-carbamoyloxymethyl-7-[2-t-butoxyimino-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 (6R,7R)-3-carbamoyloxymethyl-7-[2-(thien-2-yl)-2-methoxyiminoacetamido]ceph-3-em-4-carboxylic acid (syn isomer).
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-08-10 | 1980-02-09 | 1980-08-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-08-10 | 1984-02-09 | 1984-08-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-08-10 | 1988-02-09 | 1988-08-10 | $7700.00 | Window Closed / Lapsed |