US4563469A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Derivatives of N-[2-(tetrahydro-3,5-dioxo-1H-pyrrolizin-7a(5H)-yl)ethyl]amine as cognition activators
Assignee: Warner Lambert Co LLC
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Filing: 1984-07-20
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Granted: 1986-01-07
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Expires: 2004-07-20
Abstract
Abstract Novel derivatives of N-[2-(tetrahydro-3,5-dioxo-1H-pyrrolizin-7a(5H)-yl)ethyl]amine are effective as cognition activators for reversing the effects of electroshock induced amnesia. A method of preparing the compounds, a useful intermediate in their preparation, pharmaceutical compositions, and a method of treatment are also disclosed.
Inventors
- 👤 Donald E. Butler
- 👤 James D. Leonard
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 22:59
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/04
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
73 words
A compound having the formula ##STR4## wherein A is NR 1 R 2 where R 1 and R 2 are independently hydrogen, lower alkyl, or lower alkylene; wherein A is NHR 3 where R 3 is phenyl, phenylmethyl, N,N-bis(1-methylethyl)-aminoethyl or 4-pyridyl; or wherein A is --OR 4 where R 4 is lower alkyl, phenyl, phenylmethyl, or phenyl or phenylmethyl substituted in the 2-, 3-, or 4-position with chlorine, fluorine, lower alkoxy, or phenylmethoxy.
Claim 2
Dependent Claim
73 words
A compound having the formula ##STR4## wherein A is NR 1 R 2 where R 1 and R 2 are independently hydrogen, lower alkyl, or lower alkylene; wherein A is NHR 3 where R 3 is phenyl, phenylmethyl, N,N-bis(1-methylethyl)-aminoethyl or 4-pyridyl; or wherein A is --OR 4 where R 4 is lower alkyl, phenyl, phenylmethyl, or phenyl or phenylmethyl substituted in the 2-, 3-, or 4-position with chlorine, fluorine, lower alkoxy, or phenylmethoxy.
Claim 3
Dependent Claim
27 words
A compound in accordance with claim 1 wherein A is NR 1 R 2 where R 1 and R 2 are independently hydrogen, lower alkyl, lower allkylene.
Claim 4
Dependent Claim
19 words
A compound in accordance with claim 1 wherein A is NHR 3 where R 3 is phenyl or phenylmethyl.
Claim 5
Dependent Claim
19 words
A compound in accordance with claim 1 wherein A is NHR 3 where R 3 is N,N-bis(1-methylethyl)-aminoethyl or 4-pyridyl.
Claim 6
Dependent Claim
18 words
A compound in accodance with claim 1 wherein A is --OR 4 where R 4 is lower alkyl.
Claim 7
Dependent Claim
32 words
A compound in accordance with claim 1 wherein A is --OR 4 where R 4 is phenyl or phenyl substituted in the 2-, 3-, or 4-position with chlorine, fluorine, methoxy, or phenylmethoxy.
Claim 8
Dependent Claim
32 words
A compound in accordance with claim 1 wherein A is --OR 4 where R 4 is phenylmethyl or phenylmethyl substituted in the 2-, 3-, or 4-position with chlorine, fluorine, methoxy, or phenylmethoxy.
Claim 9
Dependent Claim
9 words
A compound in accordance with claim 2 being N-[2-(tetrahydro-3,5-dioxo-1H-pyrrolizin-7a(5H)-yl)ethyl]urea.
Claim 10
Dependent Claim
9 words
A compound in accordance with claim 2 being N-methyl-N'-[2-(tetrahydro-3,5-dioxo-1H-pyrrolizin-7a(5H)-yl)ethyl]urea.
Claim 11
Dependent Claim
9 words
A compound in accordance with claim 2 being N-2-propenyl-N'-[2-tetrahydro-3,5-dioxo-1H-pyrrolizin-7a(5H)-yl)ethyl]urea
Claim 12
Dependent Claim
9 words
A compound in accordance with claim 2 being N,N-dimethyl-N'-[2-(tetrahydro-3,5-dioxo-1H-pyrrolizin-7a(5H)-yl)ethyl]urea.
Claim 13
Dependent Claim
9 words
A compound in accordance with claim 2 being N,N-diethyl-N'-[2-(tetrahydro-3,5-dioxo-1H-pyrrolizin-7a(5H)-yl)ethyl]urea.
Claim 14
Dependent Claim
9 words
A compound in accordance with claim 3 being N-phenyl-N'-[2-tetrahydro-3,5-dioxo-1H-pyrrolizin-7a(5H)-yl)ethyl]urea.
Claim 15
Dependent Claim
9 words
A compound in accordance with claim 3 being N-(phenylmethyl)-N'-[2-(tetrahydro-3,5-dioxo-1H-pyrrolizin-7a(5H)-yl)ethyl]urea.
Claim 16
Dependent Claim
9 words
A compound in accordance with claim 4 being N-[2-[bis(1-methylethyl)amino[ethyl]-N'-[2-(tetrahydro-3,5-dioxo-1H-pyrrolizin-7a(5H)-yl)ethyl]urea.
Claim 17
Dependent Claim
9 words
A compound in accordance with claim 4 being N-4-pyridyl-N'-[2-tetrahydro-3,5-dioxo-1H-pyrrolizin-7a(5H)-yl)ethyl]urea.
Claim 18
Dependent Claim
12 words
A compound in accordance with claim 5 being [2-tetrahydro-3,5-dioxo-1H-pyrrolizin-7a(5H)-yl)ethyl]carbamic acid, methyl ester.
Claim 19
Dependent Claim
12 words
A compound in accordance with claim 5 being [2-(tetrahydro-3,5-dioxo-1H-pyrrolizin-7a(5H)-ylethyl]carbamic acid, ethyl ester.
Claim 20
Dependent Claim
12 words
A compound in accordance with claim 6 being [2-(tetrahydro-3,5-dioxo-1H-pyrrolizin-7a(5H)-yl)ethyl]carbamic acid, phenyl ester.
Claim 21
Dependent Claim
11 words
A compound in accordance with claim 6 being [2-(tetrahydro-3,5-dioxo-1H-pyrrolizin-7a(5H)-yl-ethyl]carbamic acid, 4-fluorophenylester.
Claim 22
Dependent Claim
11 words
A compound in accordance with claim 6 being [2-(tetrahydro-3,5-dioxo-1H-pyrrolizin-7a(5H)-ylethyl]carbamic acid, 2-chlorophenylester.
Claim 23
Dependent Claim
11 words
A compound in accordance with claim 6 being [2-(tetrahydro-3,5-dioxo-1H-pyrrolizin-7a(5H)-yl)ethyl]carbamic acid, 4-methoxyphenylester.
Claim 24
Dependent Claim
12 words
A compound in accordance with claim 7 being [2-tetrahydro-3,5-dioxo-1H-pyrrolizin-7a(5H)-yl)ethyl]carbamic acid, phenymethyl ester.
Claim 25
Dependent Claim
12 words
A compound in accordance with claim 7 being [2-(tetrahydro-3,5-dioxo-1H-pyrrolizin-7a(5H)-yl)ethyl]carbamic acid, [(4-methoxyphenyl)methyl] ester.
Claim 26
Dependent Claim
12 words
A compound in accodance with claim 7 being [2-(tetrahydro-3,5-dioxo-1H-pyrrolizin-7a(5H)-yl)ethyl]carbamic acid, [(3-chlorophenyl)methyl] ester.
Claim 27
Dependent Claim
18 words
An intermediate, useful in the preparation of compounds of formula I of claim 1, said intermediate being dihydro-7a(5H)-(2-isocyanatoethyl)-1H-pyrrolizin-3,5(2H,6H)-dione.
Claim 28
Dependent Claim
99 words
A pharmaceutical composition for reversing the effects of electroconvulsive shock induced amnesia comprising an amnesia-reversing effective amount of a compound having the structural formula ##STR5## wherein A is NR 1 R 2 where R 1 and R 2 are independently hydrogen, lower alkyl, or lower alkylene; wherein A is NHR 3 where R 3 is phenyl, phenylmethyl, N,N-bis(1-methylethyl)aminoethyl or 4-pyridyl; or wherein A is --OR 4 where R 4 is lower alkyl, phenyl, phenylmethyl, or phenyl or phenylmethyl substituted in the 2-, 3-, or 4-position with chlorine, fluorine, hydroxy, methoxy, or phenylmethoxy in combination with a pharmaceutically acceptable carrier.
Claim 29
Dependent Claim
99 words
A pharmaceutical composition for reversing the effects of electroconvulsive shock induced amnesia comprising an amnesia-reversing effective amount of a compound having the structural formula ##STR5## wherein A is NR 1 R 2 where R 1 and R 2 are independently hydrogen, lower alkyl, or lower alkylene; wherein A is NHR 3 where R 3 is phenyl, phenylmethyl, N,N-bis(1-methylethyl)aminoethyl or 4-pyridyl; or wherein A is --OR 4 where R 4 is lower alkyl, phenyl, phenylmethyl, or phenyl or phenylmethyl substituted in the 2-, 3-, or 4-position with chlorine, fluorine, hydroxy, methoxy, or phenylmethoxy in combination with a pharmaceutically acceptable carrier.
Claim 30
Dependent Claim
32 words
A method of reversing the effects of electroconvulsive shock-induced amnesia in a mammal which comprises administering to said mammal in need of such treatment the pharmaceutical composition in accordance with claim 27.
References Cited (Backward Citations)
EP0095345A2
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-01-06 | 1989-07-08 | 1990-01-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-01-06 | 1993-07-08 | 1994-01-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-01-06 | 1997-07-08 | 1998-01-07 | $7700.00 | Window Closed / Lapsed |