Patent US3974142A successfully refreshed from Google Patents.
US3974142A
Expired / Lapsed
US
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Penicillins
Assignee: Bayer AG
•
Filing: 1974-09-03
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Granted: 1976-08-10
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Expires: 1994-09-03
Abstract
Abstract Arylmethyl- and cyclohexenylmethyl- penicillins, substituted on the αcarbon 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
2026-10-27 19:29
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: 86
Claim 1
Independent Claim
112 words
A compound selected from the group consisting of a penicillin of the formula ##EQU17## wherein the carbon atoms 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 alkyl of 1 to 10 carbon atoms; and the pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim
112 words
A compound selected from the group consisting of a penicillin of the formula ##EQU17## wherein the carbon atoms 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 alkyl of 1 to 10 carbon atoms; and the pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim
13 words
A compound according to claim 1 which is of 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
11 words
A compound according to claim 1 wherein Q 1 is ethylene.
Claim 9
Dependent Claim
23 words
A compound according to claim 1 wherein X is --SO 2 -- and R 1 is alkyl of 1 to 4 carbon atoms.
Claim 10
Dependent Claim
28 words
A compound according to claim 1 wherein each of X and Y is --CO--; X is CO; B is phenyl; and Q 1 is ethylene, 1,2-propylene or trimethylene.
Claim 11
Dependent Claim
17 words
A compound according to claim 1 wherein the configuration about the carbon atom designated * is R.
Claim 12
Dependent Claim
17 words
A compound according to claim 1 wherein the configuration about the carbon atom designated * is S.
Claim 13
Dependent Claim
9 words
The compound according to claim 1 which is α-(3-methylsulphonylimidazolidin-2-on-1-ylcarbonylamino)benzylpenicillin.
Claim 14
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-acetyl-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-methylsulphonyl-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-n-butyryl-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-acetyl-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-acetyl-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-acetyl-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-acetyl-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-acetyl-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-acetyl-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-acetyl-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-acetyl-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 α-[(3-methylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-p-methylbenzylpenicillin, or the sodium salt thereof.
Claim 26
Dependent Claim
14 words
The compound according to claim 1 which is α-[(3-methylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-p-methoxybenzylpenicillin, or the sodium salt thereof.
Claim 27
Dependent Claim
14 words
The compound according to claim 1 which is α-[(3-methylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-p-methylthiobenzylpenicillin, or the sodium salt thereof.
Claim 28
Dependent Claim
14 words
The compound according to claim 1 which is α-[(3-methylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-p-hydroxybenzylpenicillin, or the sodium salt thereof.
Claim 29
Dependent Claim
14 words
The compound according to claim 1 which is α-[(3-methylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-p-chlorobenzylpenicillin, or the sodium salt thereof.
Claim 30
Dependent Claim
14 words
The compound according to claim 1 which is α-[(3-methylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-p-nitrobenzylpenicillin, or the sodium salt thereof.
Claim 31
Dependent Claim
14 words
The compound according to claim 1 which is α-[(3-methylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-α-thienyl(2)-methylpenicillin, or the sodium salt thereof.
Claim 32
Dependent Claim
14 words
The compound according to claim 1 which is α-[(3-methylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-α-thienyl(3)-methylpenicillin, or the sodium salt thereof.
Claim 33
Dependent Claim
14 words
The compound according to claim 1 which is α-[(3-ethylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-p-methylbenzylpenicillin, or the sodium salt thereof.
Claim 34
Dependent Claim
14 words
The compound according to claim 1 which is α-[(3-ethylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-p-methoxybenzylpenicillin, or the sodium salt thereof.
Claim 35
Dependent Claim
14 words
The compound according to claim 1 which is α-[(3-ethylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-p-methylthiobenzylpenicillin, or the sodium salt thereof.
Claim 36
Dependent Claim
14 words
The compound according to claim 1 which is α-[(3-ethylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-p-hydroxybenzylpenicillin, or the sodium salt thereof.
Claim 37
Dependent Claim
14 words
The compound according to claim 1 which is α-[(3-ethylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-p-chlorobenzylpenicillin, or the sodium salt thereof.
Claim 38
Dependent Claim
14 words
The compound according to claim 1 which is α-[(3-ethylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-p-nitrobenzylpenicillin, or the sodium salt thereof.
Claim 39
Dependent Claim
14 words
The compound according to claim 1 which is α-[(3-ethylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-α-thienyl(2)-methylpenicillin, or the sodium salt thereof.
Claim 40
Dependent Claim
14 words
The compound according to claim 1 which is α-[(3-ethylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-α-thienyl(3)-methylpenicillin, or the sodium salt thereof.
Claim 41
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-methylsulphonyl-4-methyl-imidazolidin-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 42
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-methylsulphonyl-5-methyl-imidazolidin-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 43
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-propionyl-imidazolidin-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 44
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-acetyl-4-methyl-imidazolidin-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 45
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-acetyl-5-methyl-imidazolidin-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 46
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-acetyl-1,3-diaza-cyclohexan-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 47
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-n-propylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 48
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-ethylsulphonyl-4-methyl-imidazolidin-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 49
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-ethylsulphonyl-5-methyl-imidazolidin-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 50
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-ethylsulphonyl-1,3-diaza-cyclohexan-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 51
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-methylsulphonyl-1,3-diaza-cyclohexan-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 52
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-n-propylsulonyl-1,3-diaza-cyclohexan-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 53
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-i-propylsulphonyl-1,3-diaza-cyclohexan-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 54
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-i-propylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 55
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-i-propylsulphonyl-4-methyl-imidazolidin-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 56
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-i-propylsulphonyl-5-methyl-imidazolidin-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 57
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-n-propylsulphonyl-4-methyl-imidazolidin-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 58
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-n-propylsulphonyl-5-methyl-imidazolidin-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 59
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-methylsulphonyl-4,5-dimethyl-imidazolidin-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 60
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-methylsulphonyl-4,4-dimethyl-imidazolidin-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 61
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-methylsulphonyl-5,5-dimethyl-imidazolidin-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 62
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-pivaloyl-imidazolidin-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 63
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-methylsulphonyl-imidazolidin-2-on-1-yl-carbonylamino]-1,4-cyclohexadien-yl-1-methylpenicillin, or the sodium salt thereof.
Claim 64
Dependent Claim
14 words
The compound according to claim 1 which is L(+)-α-[(3-methylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 65
Dependent Claim
14 words
The compound according to claim 1 which is α-[(3-methylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-2,6-dichloro-benzylpenicillin or the sodium salt thereof.
Claim 66
Dependent Claim
14 words
The compound according to claim 1 which is L(+)-α-[(3-acetyl-imidazolidin-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 67
Dependent Claim
14 words
The compound according to claim 1 which is α-[(3-acetyl-imidazolidin-2-on-1-yl)-carbonylamino]-2,6-dichloro-benzylpenicillin, or the sodium salt thereof.
Claim 68
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-ethylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-benzylpenicillin, or the sodium salt thereof.
Claim 69
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-methylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-4-chloro-benzylpenicillin, or the sodium salt thereof.
Claim 70
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-methylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-4-methyl-benzylpenicillin, or the sodium salt thereof.
Claim 71
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-methylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-4-benzylpenicillin, or the sodium salt thereof.
Claim 72
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-methylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-4-benzylpenicillin, or the sodium salt thereof.
Claim 73
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-methylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-.alpha.-thienyl-(2)-methylpenicillin, or the sodium salt thereof.
Claim 74
Dependent Claim
14 words
The compound according to claim 1 which is α-[(3-methylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-4-methylsulphonyl-benzylpenicillin, or the sodium salt thereof.
Claim 75
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-ethylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-4-chloro-benzylpenicillin, or the sodium salt thereof.
Claim 76
Dependent Claim
13 words
The compound according to claim 1 which D(-)-α-[(3-ethylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-4-methyl-benzylpenicillin, or the sodium salt thereof.
Claim 77
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-ethylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-4-nitro-benzylpenicillin, or the sodium salt thereof.
Claim 78
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-ethylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-4-hydroxy-benzylpenicillin, or the sodium salt thereof.
Claim 79
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-ethylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-.alpha.-thienyl-(2)-methylpenicillin, or the sodium salt thereof.
Claim 80
Dependent Claim
14 words
The compound according to claim 1 which is α-[(3-ethylsulphonyl-imidazolidin-2-on-1-yl)-carbonylamino]-4-methylsulphonyl-benzylpenicillin, or the sodium salt thereof.
Claim 81
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-acetyl-imidazolidin-2-on-1-yl)-carbonylamino]-4-chloro-benzylpenicillin, or the sodium salt thereof.
Claim 82
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-acetyl-imidazolidin-2-on-1-yl)-carbonylamino]-4-methyl-benzylpenicillin, or the sodium salt thereof.
Claim 83
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-acetyl-imidazolidin-2-on-1-yl)-carbonylamino]-4-nitro-benzylpenicillin, or the sodium salt thereof.
Claim 84
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-acetyl-imidazolidin-2-on-1-yl)-carbonylamino]-4-hydroxy-benzylpenicillin, or the sodium salt thereof.
Claim 85
Dependent Claim
14 words
The compound according to claim 1 which is D(-)-α-[(3-acetyl-imidazolidin-2-on-1-yl)-carbonylamino]-α-thienyl-(2)-methylpenicillin, or the sodium salt thereof.
Claim 86
Dependent Claim
14 words
The compound according to claim 1 which is α-[(3-acetyl-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) | 1979-08-10 | 1980-02-09 | 1980-08-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-08-10 | 1984-02-09 | 1984-08-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-08-10 | 1988-02-09 | 1988-08-10 | $7700.00 | Window Closed / Lapsed |