US3983113A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Cephalosporin type antibacterials
Assignee: Syntex USA LLC
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Filing: 1975-10-14
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Granted: 1976-09-28
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Expires: 1995-10-14
Abstract
Abstract 3-[3-(1-Methyltetrazol-5-ylthio)-prop-1-(t)-enyl]-7β-(α-substituted acetamido)-ceph-3-em-4-carboxylic acid; 7β-(α-substituted acetamido)-3-[3-(1,2,4-triazol-5-ylthio)-prop-1-(t)-enyl]-ceph-3-em-4-carboxylic acid derivatives and salts thereof; and ester intermediates and processes for preparing such compounds. The compounds are useful as antibacterials and are active against a wide variety of gram positive and gram negative bacteria.
Inventors
- 👤 Philip J. Beeby
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 03:09
CPC Classifications
C; C07; C07D; C07D501/00; C07D501/14; C07D501/16; C07D501/20; C07D501/24
Claims Analysis
Total Claims: 53
Claim 1
Independent Claim
52 words
A compound selected from the group having the formula: ##SPC30## wherein the propenyl double bond is trans; R 1 is 1-methyltetrazol-5-yl; or 1,2,4-triazol-5-yl; R 2 is hydrogen, diphenylmethyl, p-methoxybenzyl, p-nitrobenzyl, o-nitrobenzyl, benzyl, t-butyl, 2,2,2-trichloroethyl, phenacyl or pivaloyloxymethyl; R 3 is thiophen-2-yl; trifluormethylthio, phenoxy, phenylthio, (1H)-tetrazol-1-yl or sydnon-3-yl; and pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim
52 words
A compound selected from the group having the formula: ##SPC30## wherein the propenyl double bond is trans; R 1 is 1-methyltetrazol-5-yl; or 1,2,4-triazol-5-yl; R 2 is hydrogen, diphenylmethyl, p-methoxybenzyl, p-nitrobenzyl, o-nitrobenzyl, benzyl, t-butyl, 2,2,2-trichloroethyl, phenacyl or pivaloyloxymethyl; R 3 is thiophen-2-yl; trifluormethylthio, phenoxy, phenylthio, (1H)-tetrazol-1-yl or sydnon-3-yl; and pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim
34 words
The compound of claim 1 wherein said compound is selected from the group having the formula: ##SPC31## wherein R 1 and R 2 are as defined in claim 1, and pharmaceutically acceptable salts thereof.
Claim 4
Dependent Claim
10 words
The compound of claim 2 wherein R 2 is diphenylmethyl.
Claim 5
Dependent Claim
15 words
The compound of claim 2 wherein R 2 is hydrogen and pharmaceutically acceptable salts thereof.
Claim 6
Dependent Claim
10 words
The compound of claim 2 wherein R 1 is 1-methyltetrazol-5-yl.
Claim 7
Dependent Claim
21 words
The compound of claim 5 wherein said compound is selected from the group of 3-[3-(1-methyltetrazol-5-ylthio)-prop-1-(t)-enyl]-7β-(α-thiophen-2-ylacetamido)-ceph-3-em-4-carboxylic acid and pharmaceutically acceptable salts thereof.
Claim 8
Dependent Claim
12 words
The compound of claim 6 wherein said compound is a sodium salt.
Claim 9
Dependent Claim
10 words
The compound of claim 9 wherein R 1 is 1,2,4-triazol-5-yl.
Claim 10
Dependent Claim
21 words
The compound of claim 8 wherein said compound is selected from the group of 7β-(α-thiophen-2-ylacetamido)-3-[3-(1,2,4-triazol-5-ylthio)-prop-1-(t)-enyl]-ceph-3-em-4-carboxylic acid and pharmaceutically acceptable salts thereof.
Claim 11
Dependent Claim
12 words
The compound of claim 9 wherein said compound is a sodium salt.
Claim 12
Dependent Claim
34 words
The compound of claim 1 wherein said compound is selected from the group having the formula: ##SPC32## wherein R 1 and R 2 are as defined in claim 1, and pharmaceutically acceptable salts thereof.
Claim 13
Dependent Claim
10 words
The compound of claim 11 wherein R 2 is diphenylmethyl.
Claim 14
Dependent Claim
15 words
The compound of claim 11 wherein R 2 is hydrogen and pharmaceutically acceptable salts thereof.
Claim 15
Dependent Claim
10 words
The compound of claim 11 wherein R 1 is 1-methyltetrazol-5-yl.
Claim 16
Dependent Claim
21 words
The compound of claim 14 wherein said compound is selected from the group of 3-[3-(1-methyltetrazol-5-ylthio)-prop-1-(t)-enyl]-7β-(α-trifluoromethylthioacetamido)-ceph-3-em-4-carboxylic acid and pharmaceutically acceptable salts thereof.
Claim 17
Dependent Claim
12 words
The compound of claim 15 wherein said compound is a sodium salt.
Claim 18
Dependent Claim
10 words
The compound of claim 11 wherein R 1 is 1,2,4-triazol-5-yl.
Claim 19
Dependent Claim
21 words
The compound of claim 17 wherein said compound is selected from the group of 3-[3-(1-methyltetrazol-5-ylthio)-prop-1-(t)-enyl]-7β-(α-trifluoromethylthioacetamido)-ceph-3-em-4-carboxylic acid and pharmaceutically acceptable salts thereof.
Claim 20
Dependent Claim
12 words
The compound of claim 18 wherein said compound is a sodium salt.
Claim 21
Dependent Claim
40 words
The compound of claim 1 wherein said compound is selected from the group having the formula ##SPC33## wherein X is oxo or thio and R 1 and R 2 are as defined in claim 1, and pharmaceutically acceptable salts thereof.
Claim 22
Dependent Claim
10 words
The compound of claim 20 wherein R 2 is diphenylmethyl.
Claim 23
Dependent Claim
15 words
The compound of claim 20 wherein R 2 is hydrogen and pharmaceutically acceptable salts thereof.
Claim 24
Dependent Claim
10 words
The compound of claim 20 wherein R 1 is 1-methyltetrazol-5-yl.
Claim 25
Dependent Claim
21 words
The compound of claim 23 wherein said compound is selected from the group of 3-[3-(1-methyltetrazol-5-ylthio)-prop-1-(t)-enyl]-7β-(α-phenyoxyacetamido)-ceph-3-em-4-carboxylic acid and pharmaceutically acceptable salts thereof.
Claim 26
Dependent Claim
12 words
The compound of claim 24 wherein said compound is a sodium salt.
Claim 27
Dependent Claim
21 words
The compound of claim 23 wherein said compound is selected from the group of 3-[3-(1-methyltetrazol-5-ylthio)-prop-1-(t)-enyl]-7β-(α-phenylthioacetamido)-ceph-3-em-4-carboxylic acid and pharmaceutically accepted salts thereof.
Claim 28
Dependent Claim
12 words
The compound of claim 26 wherein said compound is a sodium salt.
Claim 29
Dependent Claim
10 words
The compound of claim 20 wherein R 1 is 1,2,4-triazol-5-yl.
Claim 30
Dependent Claim
21 words
The compound of claim 28 wherein said compound is selected from the group of 7β-(α-phenoxyacetamido)-3-[3-(1,2,4-triazol-5-ylthio)-prop-1-(t)-enyl]-ceph-3-em-4-carboxylic acid and pharmaceutically acceptable salts thereof.
Claim 31
Dependent Claim
12 words
The compound of claim 29 wherein said compound is a sodium salt.
Claim 32
Dependent Claim
21 words
The compound of claim 28 wherein said compound is selected from the group of 7β-(α-phenylthioacetamido)-3-[3-(1,2,4-triazol-5-ylthio)-prop-1-(t)-enyl]-ceph-3-em-4-carboxylic acid and pharmaceutically acceptable salts thereof.
Claim 33
Dependent Claim
12 words
The compound of claim 31 wherein said compound is a sodium salt.
Claim 34
Dependent Claim
34 words
The compound of claim 1 wherein said compound is selected from the group having the formula: ##SPC34## wherein R 1 and R 2 are as defined in claim 1, and pharmaceutically acceptable salts thereof.
Claim 35
Dependent Claim
10 words
The compound of claim 33 wherein R 2 is diphenylmethyl.
Claim 36
Dependent Claim
15 words
The compound of claim 33 wherein R 2 is hydrogen and pharmaceutically acceptable salts thereof.
Claim 37
Dependent Claim
10 words
The compound of claim 33 wherein R 1 is 1-methyltetrazol-5-yl.
Claim 38
Dependent Claim
21 words
The compound of claim 36 wherein said compound is selected from the group of 7β-[α-(1H)-tetrazol-1-ylacetamido]-3-[3-(1-methyltetrazol-5-ylthio)-prop-1-(t)-enyl]-ceph-3-em-4-carboxylic acid and pharmaceutically acceptable salts thereof.
Claim 39
Dependent Claim
12 words
The compound of claim 37 wherein said compound is a sodium salt.
Claim 40
Dependent Claim
10 words
The compound of claim 33 wherein R 1 is 1,2,4-triazol-5-yl.
Claim 41
Dependent Claim
21 words
The compound of claim 39 wherein said compound is selected from the group of 7β-[α-(1H)-tetrazol-1-ylacetamido]-3-[3-(1,2,4-triazol-5-ylthio)-prop-1-(t)-enyl]-ceph-3-em-4-carboxylic acid and pharmaceutically acceptable salts thereof.
Claim 42
Dependent Claim
34 words
The compound of claim 1 wherein said compound is selected from the group having the formula: ##SPC35## wherein R 1 and R 2 are as defined in claim 1, and pharmaceutically acceptable salts thereof.
Claim 43
Dependent Claim
10 words
The compound of claim 41 wherein R 2 is diphenylmethyl.
Claim 44
Dependent Claim
15 words
The compound of claim 41 wherein R 2 is hydrogen and pharmaceutically acceptable salts thereof.
Claim 45
Dependent Claim
10 words
The compound of claim 41 wherein R 1 is 1-methyltetrazol-5-yl.
Claim 46
Dependent Claim
21 words
The compound of claim 44 wherein said compound is selected from the group of 7β-[α-sydnon-3-ylacetamido]-3-[3-(1-methyltetrazol-5-ylthio)-prop-1-(t)-enyl]-ceph-3-em-4-carboxylic acid and pharmaceutically acceptable salts thereof.
Claim 47
Dependent Claim
12 words
The compound of claim 45 wherein said compound is a sodium salt.
Claim 48
Dependent Claim
10 words
The compound of claim 41 wherein R 1 is 1,2,4-triazol-5-yl.
Claim 49
Dependent Claim
21 words
The compound of claim 47 wherein said compound is selected from the group of 7β-[α-sydnon-3-ylacetamido]-3-[3-(1,2,4-triazol-5-ylthio)-prop-1-(t)-enyl]-ceph-3-em-4-carboxylic acid and pharmaceutically acceptable salts thereof.
Claim 50
Dependent Claim
25 words
The compound of claim 1 wherein said compound is selected from the group of 7β-(α-(1H)-tetrazol-1-ylacetamido)-3-[3-(1-methyltetrazol-5-ylthio)-prop-1-(t)-enyl]-ceph-3-em-4-carboxylic acid; 7β-(α-trifluoromethylthioacetamido)-3-[3-(1-methyltetrazol-5-ylthio)-prop-1-(t)-enyl]-ceph-3-em-4-carboxylic acid; 7β-(α-sydnon-3-ylacetamido)-3-[3-(1-methyltetrazol-5-ylthio)-prop-1-(t)-enyl]-ceph-3-em-4-carboxylic acid; and pharmaceutically acceptable salts thereof.
Claim 51
Dependent Claim
62 words
A process for preparing the compounds of claim 2 which comprises rearranging the C-2(3) position double bond of the corresponding 3-[3-heterocycle-ylthio)-prop-1-(t)-enyl]-7β-(thiophen-2-yl-acetamido)-ceph-2-em-4-carboxylate to C6 C-3(4) position to yield the corresponding R 2 ester of claim 2 and optionally cleaving the ester group to yield the corresponding free acid and optionally treating the acid with a pharmaceutically acceptable cation to yield the corresponding salt.
Claim 52
Dependent Claim
56 words
A process for preparing the compounds of claim 1 which comprises acylating the corresponding 7β-amino-cepheme 4-carboxylic acid or carboxylic ester with an acylating reagent corresponding to the desired R 3 acetamido substituent and optionally hydrolyzing said carboxylic ester and if desired treating the 4-carboxylic acid product with a pharmaceutically acceptable cation to yield the corresponding salt.
Claim 53
Dependent Claim
33 words
An antibacterial composition comprising an antibiotic agent selected from the compounds of claim 1 wherein R 2 is H, and pharmaceutically acceptable salts thereof, and mixtures of such compounds; and a compatible carrier.
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) | 1979-09-28 | 1980-03-29 | 1980-09-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-09-28 | 1984-03-29 | 1984-09-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-09-28 | 1988-03-29 | 1988-09-28 | $7700.00 | Window Closed / Lapsed |