US4031229A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Penicillins and processes for their preparation and use
Assignee: Bayer AG
•
Filing: 1976-06-04
•
Granted: 1977-06-21
•
Expires: 1996-06-04
Abstract
Abstract 6-[ alpha -(Imidazolidin-2-on-1-carbonylamido)acetamido]-penicillanic acids substituted in the 3-position of the imidazolidinone ring with phenyl or a substituted phenyl group and on the alpha -carbon atom of the acetamido bridge with a phenyl, thienyl, cyclohexenyl or cyclohexadienyl group, and their salts, are antibacterial agents. The compounds, of which alpha -(3-phenylimidazolidin-2-on-1-ylcarbonylamino)benzylpenicillin is a representative example, are prepared by acylation of the corresponding 6-( alpha -aminoacetamido)penicillanic acid or a derivative thereof.
Inventors
- 👤 Hans-Bodo Konig
- 👤 Karl Georg Metzger
- 👤 Wilfried Schrock
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 10:10
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/04; C07D233/28; C07D233/30; C07D233/32; C07D233/38; C07D499/00
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
160 words
A compound selected from the group consisting of a penicillin of the formula: ##STR39## and the pharmaceutically acceptable salts thereof, wherein the carbon atom designated * constitutes a center of chirality; A is hydrogen or methoxy; B is phenyl, hydroxyphenyl, halophenyl, methoxyphenyl, cyanophenyl, methylsulfonylphenyl, thienyl, cyclohexenyl or cyclohexa-1,4-dien-1-yl; each of R, R 1 and R 2 is independently selected from the group consisting of hydrogen, halo, lower alkyl, halo(lower)alkyl, carboxy, formyl, carbo(lower alkoxy), lower alkanoyl, cyano, carbamyl, lower alkylcarbamyl, di(lower alkyl)carbamyl, lower alkylamino, di(lower alkyl)amino, pyrrolidino, piperidino, formamido, lower alkanamido, N-(lower alkyl)formamido, N-(lower alkyl)lower alkanamido, lower alkylidenimino, lower alkylsulfonamido, n-(lower alkyl)lower alkylsulfonamido, sulfamino, N-(lower alkyl)sulfamino, amidino, di(lower alkyl)aminomethylidenimino, pyrrolidinomethylidenimino, guanido, nitro, azido, carbo(lower alkoxy)amino, N-(lower alkyl)carbo(lower alkoxy)-amino, hydroxy, lower alkoxy, formyloxy, lower alkanoyloxy, lower alkoxycarbonyloxy, carbamyloxy, N-(lower alkyl)carbamyloxy, N,N-di(lower alkyl)-carbamyloxy, pyrrolidinocarboxyloxy, sulfamyl, N-(lower alkyl)sulfamyloxy, N,N-di(lower alkyl)-sulfamyloxy, mercapto, lower alkylthio, trifluoromethylthio, lower alkylsulfonyl, sulfo, lower alkylsulfinyl, trifluoromethylsulfonyl, sulfamyl, N-(lower alkyl)sulfamyl, N,N-di(lower alkyl)sulfamyl, pyrrolidinosulfonyl, and sulfothio; and E is oxygen or sulfur.
Claim 2
Dependent Claim
160 words
A compound selected from the group consisting of a penicillin of the formula: ##STR39## and the pharmaceutically acceptable salts thereof, wherein the carbon atom designated * constitutes a center of chirality; A is hydrogen or methoxy; B is phenyl, hydroxyphenyl, halophenyl, methoxyphenyl, cyanophenyl, methylsulfonylphenyl, thienyl, cyclohexenyl or cyclohexa-1,4-dien-1-yl; each of R, R 1 and R 2 is independently selected from the group consisting of hydrogen, halo, lower alkyl, halo(lower)alkyl, carboxy, formyl, carbo(lower alkoxy), lower alkanoyl, cyano, carbamyl, lower alkylcarbamyl, di(lower alkyl)carbamyl, lower alkylamino, di(lower alkyl)amino, pyrrolidino, piperidino, formamido, lower alkanamido, N-(lower alkyl)formamido, N-(lower alkyl)lower alkanamido, lower alkylidenimino, lower alkylsulfonamido, n-(lower alkyl)lower alkylsulfonamido, sulfamino, N-(lower alkyl)sulfamino, amidino, di(lower alkyl)aminomethylidenimino, pyrrolidinomethylidenimino, guanido, nitro, azido, carbo(lower alkoxy)amino, N-(lower alkyl)carbo(lower alkoxy)-amino, hydroxy, lower alkoxy, formyloxy, lower alkanoyloxy, lower alkoxycarbonyloxy, carbamyloxy, N-(lower alkyl)carbamyloxy, N,N-di(lower alkyl)-carbamyloxy, pyrrolidinocarboxyloxy, sulfamyl, N-(lower alkyl)sulfamyloxy, N,N-di(lower alkyl)-sulfamyloxy, mercapto, lower alkylthio, trifluoromethylthio, lower alkylsulfonyl, sulfo, lower alkylsulfinyl, trifluoromethylsulfonyl, sulfamyl, N-(lower alkyl)sulfamyl, N,N-di(lower alkyl)sulfamyl, pyrrolidinosulfonyl, and sulfothio; and E is oxygen or sulfur.
Claim 3
Dependent Claim
50 words
A compound according to claim 1 wherein said penicillin is of the formula: ##STR40## and the pharmaceutically acceptable salts thereof, wherein the carbon atom designated * constitutes a center of chirality; B is phenyl, hydroxyphenyl, chlorophenyl, cyclohexenyl or cyclohexa-1,4-dien-1-yl; and R is hydrogen, halo, cyano, lower alkoxy or lower alkylsulfamyl.
Claim 4
Dependent Claim
22 words
A compound according to claim 2 wherein B is phenyl, 4-hydroxyphenyl or cyclohexa-1,4-dien-1-yl; and R is hydrogen, chloro, cyano, methoxy or methylsulfamyl.
Claim 5
Dependent Claim
45 words
A compound according to claim 1 which is a salt of said penicillin, said salt being selected from the group consisting of the sodium, potassium, magnesium, calcium, aluminium, di(lower alkyl)amine, tri(lower alkyl)amine, procaine, dibenzylamine, N,N'-dibenzylethylenediamine, N-benzyl-β-phenylethylamine, N-methylmorpholine, N-ethylmorpholine, 1-ephenamine, dehydroabietylamine, N,N'-bis-dehydroabietylethylenediamine and N-(lower alkyl)piperidine salts.
Claim 6
Dependent Claim
11 words
A compound according to claim 1 wherein said penicillin is α-(3-phenylimidazolidin-2-on-1-ylcarbonylamino)-benzylpenicillin.
Claim 7
Dependent Claim
11 words
A compound according to claim 1 wherein said penicillin is α-(3-phenylimidazolidin-2-on-1-ylcarbonylamino)-4-hydroxybenzylpenicillin.
Claim 8
Dependent Claim
11 words
A compound according to claim 1 wherein said penicillin is α-(3-phenylimidazolidin-2-on-1-ylcarbonylamino)-α-(cyclohexa-1,4-dien-1-yl)methylpenicillin.
Claim 9
Dependent Claim
11 words
A compound according to claim 1 wherein said penicillin is α-[3-(4-methoxyphenyl)imidazolidin-2-on-1-yl-carbonylamino]benzylpenicillin.
Claim 10
Dependent Claim
11 words
A compound according to claim 1 wherein said penicillin is α-[3-(4-methoxyphenyl)imidazolidin-2-on-1-yl-carbonylamino]-4-hydroxybenzylpenicillin.
Claim 11
Dependent Claim
11 words
A compound according to claim 1 wherein said penicillin is α-[3-(4-methylaminosulfonylphenyl)imidazolidin-2-on-1-ylcarbonylamino]benzylpenicillin.
Claim 12
Dependent Claim
11 words
A compound according to claim 1 wherein said penicillin is α-[3-(4-methylaminosulfonylphenyl)imidazolidin-2-on-1-ylcarbonylamino]-4-hydroxybenzylpenicillin.
Claim 13
Dependent Claim
33 words
A pharmaceutical composition for treating bacterial infections in humans and other animals which comprises an antibacterially effective amount of a compound according to claim 1 in combination with a pharmaceutically acceptable nontoxic carrier.
Claim 14
Dependent Claim
26 words
A method of treating bacterial infections in humans and other animals which comprises administering thereto an antibacterially effective amount of a compound according to claim 1.
Claim 15
Dependent Claim
22 words
A growth-promoting composition which comprises an antibacterially effective amount of a compound according to claim 1 in combination with an edible carrier.
Claim 16
Dependent Claim
30 words
A method of promoting growth in livestock animals which comprises administering to such animals a growth-promoting amount of a compound according to claim 1 in combination with an edible 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) | 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 |