US3983105A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Penicillins
Assignee: Bayer AG
•
Filing: 1974-09-03
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Granted: 1976-09-28
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Expires: 1994-09-03
Abstract
Abstract Arylmethyl- and cyclohexenylmethyl- penicillins, substituted on the alpha -carbon atom of the side chain by a 2,3-disubstituted imidazolidinylcarbamido or a 2,3-disubstituted imidazolidinylthiocarbamido group, or by the corresponding 2,3-disubstituted 1,3-diazacyclohexylcarbamido or thiocarbamido groups are anti-bacterial agents.
Inventors
- 👤 Hans-Bodo Konig
- 👤 Wilfried Schrock
- 👤 Karl Georg Metzger
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 04:29
CPC Classifications
C; C07; C07D; C07D275/00; C07D275/02; C07D233/00; C07D233/04; C07D233/28; C07D233/30; C07D233/32; C07D233/38; C07D333/00; C07D333/02; C07D333/04; C07D333/26; C07D333/30; C07D333/34; C07D499/00
Claims Analysis
Total Claims: 34
Claim 1
Independent Claim
170 words
A compound selected from the group consisting of a penicillin of the formula ##EQU102##wherein the carbon atom designated by * constitutes a center of chirality; X is --CO--, --CS-- or --SO 2 --; each of Y and Z, independently of the other, is --CO-- or --CS--; B is thienyl, cyclohexenyl, cyclohexa-1,4-dien-1-yl, phenyl or phenyl substituted by one or two members selected from the group consisting of halo, nitro, hydroxy, methoxy, methylthio and alkyl of 1 to 5 carbon atoms; Q 1 is ethylene or trimethylene unsubstituted or substituted by one or two methyl groups; and R 1 is phenylamino; the group ##SPC64## in which n is 0, 1 or 2 and each of R 4 , R 5 and R 6 , independently of the others, is hydrogen, nitro, cyano, halo, trifluoromethyl, R, (R) 2 N, (R) 2 NCO--, RCONH--, ROCO, RCOO or RO where R is alkyl of 1 to 5 carbon atoms; or when X is other than --SO 2 --, phenoxy; and the pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim
170 words
A compound selected from the group consisting of a penicillin of the formula ##EQU102##wherein the carbon atom designated by * constitutes a center of chirality; X is --CO--, --CS-- or --SO 2 --; each of Y and Z, independently of the other, is --CO-- or --CS--; B is thienyl, cyclohexenyl, cyclohexa-1,4-dien-1-yl, phenyl or phenyl substituted by one or two members selected from the group consisting of halo, nitro, hydroxy, methoxy, methylthio and alkyl of 1 to 5 carbon atoms; Q 1 is ethylene or trimethylene unsubstituted or substituted by one or two methyl groups; and R 1 is phenylamino; the group ##SPC64## in which n is 0, 1 or 2 and each of R 4 , R 5 and R 6 , independently of the others, is hydrogen, nitro, cyano, halo, trifluoromethyl, R, (R) 2 N, (R) 2 NCO--, RCONH--, ROCO, RCOO or RO where R is alkyl of 1 to 5 carbon atoms; or when X is other than --SO 2 --, phenoxy; and the pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim
12 words
A compound according to claim 1 which is an alkali metal salt.
Claim 4
Dependent Claim
11 words
A compound according to claim 1 which is the sodium salt.
Claim 5
Dependent Claim
10 words
A compound according to claim 1 wherein Y is --CO--.
Claim 6
Dependent Claim
20 words
A compound according to claim 1 wherein B is thienyl, cyclohexenyl, cyclohexa-1,4-dien-1-yl, phenyl, halophenyl, hydroxyphenyl, nitrophenyl, methoxyphenyl, methylphenyl, or methylthiophenyl.
Claim 7
Dependent Claim
39 words
A compound according to claim 1 wherein each of Z and Y is --CO--; B is thienyl, cyclohexenyl, cyclohexa-1,4-dien-1-yl, phenyl, halophenyl or hydroxyphenyl; and Q 1 is ethylene or trimethylene, unsubstituted or substituted by one or two methyl groups.
Claim 8
Dependent Claim
24 words
A compound according to claim 1 wherein each of Z and Y is --CO--; B is phenyl; and Q is ethylene, 1,2-propylene or trimethylene.
Claim 9
Dependent Claim
10 words
A compound according to claim 7 wherein Q is ethylene.
Claim 10
Dependent Claim
18 words
A compound according to claim 8 wherein X is --CO-- and R 1 is phenyl, phenoxy or phenylamino.
Claim 11
Dependent Claim
17 words
A compound according to claim 8 wherein X is --SO 2 -- and R 1 is phenyl.
Claim 12
Dependent Claim
17 words
A compound according to claim 1 wherein the configuration about the carbon atom designated * is R.
Claim 13
Dependent Claim
17 words
A compound according to claim 1 wherein the configuration about the carbon atom designated * is S.
Claim 14
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-phenylaminocarbonyl-imidazolidin-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 15
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-phenoxycarbonyl-imidazolidin-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 16
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-benzoyl-imidazolidin-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 17
Dependent Claim
14 words
The compound according to claim 1 which is α-[(3-phenoxycarbonyl-imidazolidin-2-on-1-yl)-carbonylamino]-p-methylbenzylpenicillin, or the sodium salt thereof.
Claim 18
Dependent Claim
14 words
The compound according to claim 1 which is α-[(3-phenoxycarbonyl-imidazolidin-2-on-1-yl)-carbonylamino]-p-methoxybenzylpenicillin, or the sodium salt thereof.
Claim 19
Dependent Claim
14 words
The compound according to claim 1 which is α-[(3-phenoxycarbonyl-imidazolidin-2-on-1-yl)-carbonylamino]-p-methylthiobenzylpenicillin, or the sodium salt thereof.
Claim 20
Dependent Claim
14 words
The compound according to claim 1 which is α-[(3-phenoxycarbonyl-imidazolidin-2-on-1-yl)-carbonylamino]-p-hydroxybenzylpenicillin, or the sodium salt thereof.
Claim 21
Dependent Claim
14 words
The compound according to claim 1 which is α-[(3-phenoxycarbonyl-imidazolidin-2-on-1-yl)-carbonylamino]-p-chlorobenzylpenicillin, or the sodium salt thereof.
Claim 22
Dependent Claim
14 words
The compound according to claim 1 which is α-[(3-phenoxycarbonyl-imidazolidin-2-on-1-yl)-carbonylamino]-p-nitrobenzylpenicillin, or the sodium salt thereof.
Claim 23
Dependent Claim
14 words
The compound according to claim 1 which is α-[(3-phenoxycarbonyl-imidazolidin-2-on-1-yl)-carbonylamino]-α-thienyl(2)-methylpenicillin, or the sodium salt thereof.
Claim 24
Dependent Claim
14 words
The compound according to claim 1 which is α-[(3-phenoxycarbonyl-imidazolidin-2-on-1-yl)-carbonylamino]-α-thienyl(3)-methylpenicillin, or the sodium salt thereof.
Claim 25
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-p-methoxybenzoyl-imidazolidin-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 26
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-phenylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 27
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-p-methylphenylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 28
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-phenylsulphonyl-1,3-diaza-cyclohexan-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 29
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-benzoyl-imidazolidin-2-on-1-yl)-carbonylamino]-4-chloro-benzylpenicillin, or the sodium salt thereof.
Claim 30
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-benzoyl-imidazolidin-2-on-1-yl)-carbonylamino]-4-methyl-benzylpenicillin, or the sodium salt thereof.
Claim 31
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-benzoyl-imidazolidin-2-on-1-yl)-carbonylamino]-4-nitrobenzylpenicillin, or the sodium salt thereof.
Claim 32
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-benzoyl-imidazolidin-2-on-1-yl)-carbonylamino]-4-hydroxy-benzylpenicillin, or the sodium salt thereof.
Claim 33
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-benzoyl-imidazolidin-2-on-1-yl)-carbonylamino]-α-thienyl(2)-methylpenicillin, or the sodium salt thereof.
Claim 34
Dependent Claim
14 words
The compound according to claim 1 which is α-[(3-benzoyl-imidazolidin-2-on-1-yl)-carbonylamino]-4-methylsulphonyl-benzylpenicillin, or the sodium salt thereof.
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 |