US4031077A
Expired / Lapsed
US
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Antibacterial 3-phosphono penams
Assignee: Pfizer Inc
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Filing: 1976-04-26
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Granted: 1977-06-21
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Expires: 1996-04-26
Abstract
Abstract The present invention discloses novel 6-acylamino-2,2-dimethyl-3-phosphonopenams and certain lower alkyl esters thereof possessing antibacterial activity, methods for their production, and intermediates therefor; the production comprises the steps of reacting 6-triphenylmethylamino-2,2-dimethylpenam-3-carboxylic acid with lead tetraacetate to form the corresponding 3-acetoxy compound, the latter is converted to alpha -triphenylmethylamino-5,5-dimethyl-3-thiazoline-2-acetic acid which is condensed with dimethyl phosphite to produce alpha -triphenylmethylamino-5,5-dimethyl-4(0,0-dimethylphosphono)-thiazolidi ne-2-acetic acid which is cyclized to 6-triphenylmethylamino-2,2-dimethyl-3-(0,0-dimethylphosphono)penam and the latter is subsequently deblocked and acylated.
Inventors
- 👤 Wayne E. Barth
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 11:52
CPC Classifications
C; C07; C07D; C07D499/00; A; A23; A23K; A23K20/00; A23K20/10; A23K20/116; A23K20/137; A61; A61P; A61P31/00; A61P31/04; C07D277/00; C07D277/02; C07D277/08; C07D277/10; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/6561; C07F9/65611
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
123 words
A compound of the formula (I) ##STR31## and the pharmaceutically acceptable salts thereof, wherein R 2 and R 3 are the same or different and are selected from the group consisting of hydrogen and methyl; R 1 is selected from the group consisting of phenyl, phenoxy, 1,4-cyclohexadienyl, thienyl and phenyl monosubstituted by a member selected from the group consisting of hydroxy, and aminomethyl, and Q is selected from the group consisting of hydrogen, amino, carboxy and sulfo; provided that: when R 1 is selected from the group consisting of phenoxy and phenyl monosubstituted by aminomethyl, Q is hydrogen; when Q is carboxy, R 1 is selected from the group consisting of phenyl and thienyl; and when Q is sulfo, R 1 is phenyl.
Claim 2
Dependent Claim
123 words
A compound of the formula (I) ##STR31## and the pharmaceutically acceptable salts thereof, wherein R 2 and R 3 are the same or different and are selected from the group consisting of hydrogen and methyl; R 1 is selected from the group consisting of phenyl, phenoxy, 1,4-cyclohexadienyl, thienyl and phenyl monosubstituted by a member selected from the group consisting of hydroxy, and aminomethyl, and Q is selected from the group consisting of hydrogen, amino, carboxy and sulfo; provided that: when R 1 is selected from the group consisting of phenoxy and phenyl monosubstituted by aminomethyl, Q is hydrogen; when Q is carboxy, R 1 is selected from the group consisting of phenyl and thienyl; and when Q is sulfo, R 1 is phenyl.
Claim 3
Dependent Claim
22 words
A compound according to claim 1, wherein R 1 is selected from the group consisting of phenyl, 1,4-cyclohexadienyl, 4-hydroxyphenyl, 2-thienyl and 3-thienyl.
Claim 4
Dependent Claim
24 words
A compound according to claim 1, wherein R 1 is selected from the group consisting of phenyl, phenoxy, and 2-aminomethylphenyl and Q is hydrogen.
Claim 5
Dependent Claim
10 words
A compound according to claim 2, wherein Q is amino.
Claim 6
Dependent Claim
11 words
A compound according to claim 4, wherein R 1 is phenyl.
Claim 7
Dependent Claim
11 words
A compound according to claim 4, wherein R 1 is 4-hydroxyphenyl.
Claim 8
Dependent Claim
11 words
A compound according to claim 4, wherein R 1 is 3-thienyl.
Claim 9
Dependent Claim
11 words
A compound according to claim 4, wherein R 1 is 1,4-cyclohexadienyl.
Claim 10
Dependent Claim
15 words
A compound according to claim 1, wherein Q is carboxy and R 1 is phenyl.
Claim 11
Dependent Claim
15 words
A compound according to claim 1, wherein Q is carboxy and R 1 is thienyl.
Claim 12
Dependent Claim
15 words
A compound according to claim 1, wherein Q is sulfo and R 1 is phenyl.
Claim 13
Dependent Claim
21 words
The compound of claim 1 wherein R 1 is phenoxy and each of Q, R 2 and R 3 are hydrogen.
References Cited (Backward Citations)
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1980-06-20 | 1980-12-20 | 1981-06-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-06-20 | 1984-12-20 | 1985-06-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-06-20 | 1988-12-20 | 1989-06-21 | $7700.00 | Window Closed / Lapsed |