US3956314A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Derivatives of 2-pyrrolidinone
Assignee: UCB SA
•
Filing: 1973-11-20
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Granted: 1976-05-11
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Expires: 1993-11-20
Abstract
Abstract Phenyl-2-pyrrolidinones of the formula WHEREIN R is a halogen or trifluoromethyl, R1 is lower alkyl, lower alkenyl, lower alkynyl, phenyl or halogen-substituted phenyl, R2 is hydrogen, lower alkyl or phenyl and R3 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, cyclopentyl or benzyl, as well as the cis and trans diastereoisomers thereof, are active on the central nervous system. In particular they have valuable anxiolytic and antidepressive properties. Processes for their preparation are given.
Inventors
- 👤 Joseph Honore Strubbe
- 👤 Raymond Armand Linz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 16:31
CPC Classifications
C; C07; C07C; C07C255/00; C07C205/00; C07C205/49; C07C205/56
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
42 words
A compound selected from the group consisting of 4-p-chlorophenyl-3-ethyl-2-pyrrolidinone, 4-p-chlorophenyl-3-methyl-2-pyrrolidinone, 4-p-chlorophenyl-3-phenyl-2-pyrrolidinone, 4-o-chlorophenyl-3-phenyl-2-pyrrolidinone, 4-p-fluorophenyl-3-methyl-2pyrrolidinone, 4-p-chlorophenyl-N-methyl-3-phenyl-2-pyrrolidinone, 4-p-fluorophenyl-3-phenyl-2-pyrrolidinone, 3-o-chlorophenyl-4-p-chlorophenyl-2-pyrrolidinone, 4-p-chlorophenyl-4-phenyl-2-pyrrolidinone, N-benzyl-4-p-chlorophenyl-3-phenyl-2-pyrrolidinone, 4-p-chlorophenyl-5-ethyl-3-phenyl-2-pyrrolidinone, 4-p-chlorophenyl-3-phenyl-N-(2-propynyl)-2-pyrrolidinone, 4-p-chlorophenyl-N-cyclopentyl-3-phenyl-2-pyrrolidinone, 3-allyl-3-p-chlorophenyl-5-phenyl-2-pyrrolidinone, 3-phenyl-4-m-trifluoromethylphenyl-2-pyrrolidinone, 4-p-chlorophenyl-3,3-dimethyl-2-pyrrolidinone, 3,4-bis-p-chlorophenyl-2-pyrrolidinone, 3-p-chlorophenyl-4-phenyl-2-pyrrolidinone, 4-m-chlorophenyl-3-phenyl-2-pyrrolidinone, 4-m-fluorophenyl-3-phenyl-2-pyrrolidinone, 4-p-chlorophenyl-4-methyl-3-phenyl-2-pyrrolidinone, 4-o-fluorophenyl-3-phenyl-2-pyrrolidinone, 4-p-chlorophenyl-5-methyl-2-pyrrolidinone, 4-p-chlorophenyl-5,5-dimethyl-2-pyrrolidinone, 3-allyl-3-p-chlorophenyl-2-pyrrolidinone, 3-methyl-4-p-nitrophenyl-2-pyrrolidinone, 4-p-aminophenyl-3-methyl-2-pyrrolidinone, 4-p-bromophenyl-3-methyl-2-pyrrolidinone, 4-p-chlorophenyl-N-methyl-3-methyl-2-pyrrolidinone, N-allyl-4-p-chlorophenyl-3-phenyl-2-pyrrolidinone, N-n-butyl-4-p-chlorophenyl-3-phenyl-2-pyrrolidinone, 4-p-chlorophenyl-N-n-hexyl-3-phenyl-2-pyrrolidinone and 4-p-chlorophenyl-5-phenyl-2-pyrrolidinone.
Claim 2
Dependent Claim
42 words
A compound selected from the group consisting of 4-p-chlorophenyl-3-ethyl-2-pyrrolidinone, 4-p-chlorophenyl-3-methyl-2-pyrrolidinone, 4-p-chlorophenyl-3-phenyl-2-pyrrolidinone, 4-o-chlorophenyl-3-phenyl-2-pyrrolidinone, 4-p-fluorophenyl-3-methyl-2pyrrolidinone, 4-p-chlorophenyl-N-methyl-3-phenyl-2-pyrrolidinone, 4-p-fluorophenyl-3-phenyl-2-pyrrolidinone, 3-o-chlorophenyl-4-p-chlorophenyl-2-pyrrolidinone, 4-p-chlorophenyl-4-phenyl-2-pyrrolidinone, N-benzyl-4-p-chlorophenyl-3-phenyl-2-pyrrolidinone, 4-p-chlorophenyl-5-ethyl-3-phenyl-2-pyrrolidinone, 4-p-chlorophenyl-3-phenyl-N-(2-propynyl)-2-pyrrolidinone, 4-p-chlorophenyl-N-cyclopentyl-3-phenyl-2-pyrrolidinone, 3-allyl-3-p-chlorophenyl-5-phenyl-2-pyrrolidinone, 3-phenyl-4-m-trifluoromethylphenyl-2-pyrrolidinone, 4-p-chlorophenyl-3,3-dimethyl-2-pyrrolidinone, 3,4-bis-p-chlorophenyl-2-pyrrolidinone, 3-p-chlorophenyl-4-phenyl-2-pyrrolidinone, 4-m-chlorophenyl-3-phenyl-2-pyrrolidinone, 4-m-fluorophenyl-3-phenyl-2-pyrrolidinone, 4-p-chlorophenyl-4-methyl-3-phenyl-2-pyrrolidinone, 4-o-fluorophenyl-3-phenyl-2-pyrrolidinone, 4-p-chlorophenyl-5-methyl-2-pyrrolidinone, 4-p-chlorophenyl-5,5-dimethyl-2-pyrrolidinone, 3-allyl-3-p-chlorophenyl-2-pyrrolidinone, 3-methyl-4-p-nitrophenyl-2-pyrrolidinone, 4-p-aminophenyl-3-methyl-2-pyrrolidinone, 4-p-bromophenyl-3-methyl-2-pyrrolidinone, 4-p-chlorophenyl-N-methyl-3-methyl-2-pyrrolidinone, N-allyl-4-p-chlorophenyl-3-phenyl-2-pyrrolidinone, N-n-butyl-4-p-chlorophenyl-3-phenyl-2-pyrrolidinone, 4-p-chlorophenyl-N-n-hexyl-3-phenyl-2-pyrrolidinone and 4-p-chlorophenyl-5-phenyl-2-pyrrolidinone.
Claim 3
Dependent Claim
12 words
The compound according to claim 1, namely the cis diastereoisomer of 4-p-chlorophenyl-3-phenyl-2-pyrrolidinone.
Claim 4
Dependent Claim
12 words
The compound according to claim 1, namely the trans diastereoisomer of 4-p-chlorophenyl-3-phenyl-2-pyrrolidinone.
Claim 5
Dependent Claim
12 words
The compound according to claim 1, namely the cis diastereoisomer of 4-p-chlorophenyl-3-methyl-2-pyrrolidinone.
Claim 6
Dependent Claim
12 words
The compound according to claim 1, namely the trans diastereoisomer of 4-p-chlorophenyl-3-methyl-2-pyrrolidinone.
Claim 7
Dependent Claim
9 words
The compound according to claim 1, namely the 4-p-chlorophenyl-N-methyl-3-phenyl-2--pyrrolidinone.
Claim 8
Dependent Claim
9 words
The compound according to claim 1, namely the 4-p-fluorophenyl-3-phenyl-2-pyrrolidinone.
Claim 9
Dependent Claim
9 words
The compound according to claim 1, namely the 4-m-chlorophenyl-3-phenyl-2-pyrrolidinone.
Claim 10
Dependent Claim
9 words
The compound according to claim 1, namely the 3-o-chlorophenyl-4-p-chlorophenyl-2-pyrrolidinone.
Claim 11
Dependent Claim
12 words
The compound according to claim 1, namely the trans diastereoisomer of 4-p-chlorophenyl-3-ethyl-2-pyrrolidinone.
Claim 12
Dependent Claim
8 words
The compound according to claim 1, namely 3-phenyl-4-m-trifluoromethylphenyl-2-pyrrolidinone.
References Cited (Backward Citations)
US3471548A
Cited
US3804854A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-05-11 | 1979-11-10 | 1980-05-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-05-11 | 1983-11-10 | 1984-05-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-05-11 | 1987-11-10 | 1988-05-11 | $7700.00 | Window Closed / Lapsed |