US4096330A
Expired / Lapsed
US
⏱️ 0.0 years remaining
7β-[[[(2-Cyanomethyl)amino]-1,2-dioxoethyl]amino]acyl cephalosporins
Assignee: ER Squibb and Sons LLC
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Filing: 1977-04-21
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Granted: 1978-06-20
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Expires: 1997-04-21
Abstract
Abstract 7β-[[[(2-Cyanomethyl)amino]-1,2-dioxoethyl]amino]-acyl cephalosporins which have the formula ##STR1## wherein R is hydrogen, lower alkyl, phenyl-lower alkyl, diphenyl-lower alkyl, tri(lower alkyl)silyl, tri(lower alkyl)stannyl, trihaloethyl or a salt forming ion; R 1 is hydrogen, lower alkyl, saturated or unsaturated cycloalkyl, phenyl, phenyl-lower alkyl, substituted phenyl or certain heterocyclic groups; R 2 is hydrogen or methoxy; R 3 is hydrogen, lower alkyl, phenyl-lower alkyl or cycloalkyl; R 4 and R 5 each is hydrogen or lower alkyl; and X is hydrogen, lower alkanoyloxy, carbamoyloxy, lower alkoxy, lower alkylthio ##STR2## or certain heterothio groups, are useful as antibacterial agents.
Inventors
- 👤 Uwe D. Treuner
- 👤 Hermann Breuer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 21:19
CPC Classifications
C; C07; C07C; C07C255/00
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
149 words
A compound of the formula ##STR154## wherein R is hydrogen, lower alkyl, phenyl-lower alkyl, diphenyl-lower alkyl, tri(lower alkyl)silyl, tri(lower alkyl)stannyl, trihaloethyl, aluminum, alkali metal, alkaline earth metal phenyl-lower alkyl amine, N, N-dibenzylethylene-diamine, lower, alkylemine, triethyamine, or N-lower alkyl piperdine; R 1 is phenyl, phenyl-lower alkyl, substituted phenyl wherein said phenyl substituent is one or two members selected from the group consisting of halogen, lower alkyl, lower alkoxy, and hydroxy, or a heterocyclic selected from the group consisting of 2-thienyl, 3-thienyl, 2-furyl and 3-furyl; R 2 is hydrogen or methoxy; R 3 is hydrogen, lower alkyl, phenyl-lower alkyl or cycloalkyl; R 4 and R 5 each is hydrogen or lower alkyl; and X is a heterothio group selected from the group consisting of ##STR155## R 6 is hydrogen or lower alkyl; and R 7 is carboxy, COO.sup.⊖ ion .sup.⊕, --COO-lower alkyl, SO 3 H, --SO 2 -lower alkyl or cyano.
Claim 2
Dependent Claim
149 words
A compound of the formula ##STR154## wherein R is hydrogen, lower alkyl, phenyl-lower alkyl, diphenyl-lower alkyl, tri(lower alkyl)silyl, tri(lower alkyl)stannyl, trihaloethyl, aluminum, alkali metal, alkaline earth metal phenyl-lower alkyl amine, N, N-dibenzylethylene-diamine, lower, alkylemine, triethyamine, or N-lower alkyl piperdine; R 1 is phenyl, phenyl-lower alkyl, substituted phenyl wherein said phenyl substituent is one or two members selected from the group consisting of halogen, lower alkyl, lower alkoxy, and hydroxy, or a heterocyclic selected from the group consisting of 2-thienyl, 3-thienyl, 2-furyl and 3-furyl; R 2 is hydrogen or methoxy; R 3 is hydrogen, lower alkyl, phenyl-lower alkyl or cycloalkyl; R 4 and R 5 each is hydrogen or lower alkyl; and X is a heterothio group selected from the group consisting of ##STR155## R 6 is hydrogen or lower alkyl; and R 7 is carboxy, COO.sup.⊖ ion .sup.⊕, --COO-lower alkyl, SO 3 H, --SO 2 -lower alkyl or cyano.
Claim 3
Dependent Claim
11 words
A compound as in claim 1 wherein R 1 is thienyl.
Claim 4
Dependent Claim
11 words
A compound as in claim 1 wherein R 1 is phenyl.
Claim 5
Dependent Claim
11 words
A compound as in claim 1 wherein R 1 is furyl.
Claim 6
Dependent Claim
10 words
A compound as in claim 1 wherein X is methyltetrazolyl.
Claim 7
Dependent Claim
48 words
A compound as in claim 1 wherein R is hydrogen or alkali metal; R 1 is phenyl, thienyl or furyl; R 2 is hydrogen or methoxy; R 3 , R 4 and R 5 each is hydrogen or lower alkyl; and X is as defined in claim 1.
Claim 8
Dependent Claim
43 words
A compound as in claim 1 wherein R is hydrogen, sodium or potassium; R 1 is phenyl or thienyl; R 2 is hydrogen; R 3 is hydrogen or methyl; R 4 and R 5 each is hydrogen and X is acetoxy or (1-methyl-1H-tetrazol-5-yl)thio.
Claim 9
Dependent Claim
30 words
A compound as in claim 1 wherein R, R 2 , R 3 , R 4 and R 5 each is hydrogen; R 1 is 2-thienyl; and X is (1-methyl-1H-tetrazol-5-yl)thio.
Claim 10
Dependent Claim
32 words
A compound as in claim 1 wherein R is sodium, R 2 , R 3 , R 4 and R 5 each is hydrogen; R 1 is 2-thienyl; and X is (1-methyl-1H-tetrazol-5-yl)thio.
Claim 11
Dependent Claim
31 words
A compound as in claim 1 wherein X is a heterothio group selected from the group consisting of ##STR156## wherein R 6 is hydrogen or C 1 -C 4 -lower alkyl.
Claim 12
Dependent Claim
8 words
The D-isomer of a compound of claim 1.
Claim 13
Dependent Claim
8 words
The D-isomer of the compound of claim 8.
Claim 14
Dependent Claim
8 words
The D-isomer of the compound of claim 9.
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) | 1981-06-19 | 1981-12-19 | 1982-06-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-06-19 | 1985-12-19 | 1986-06-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-06-19 | 1989-12-19 | 1990-06-20 | $7700.00 | Window Closed / Lapsed |