Patent US4772601A successfully refreshed from Google Patents.
US4772601A
Expired / Lapsed
US
⏱️ 0.0 years remaining
5-Substituted 1-(4-(1-pyrrolidinyl)-2-butynyl)-2-pyrrolidinones, pharmaceutical compositions and use
Assignee: Aventis Pharmaceuticals Inc
•
Filing: 1988-01-25
•
Granted: 1988-09-20
•
Expires: 2008-01-25
Abstract
Abstract There are disclosed compounds of the formula ##STR1## where R 1 is loweralkoxycarbonyl, --CH 2 OH or --CONR 3 R 4 , R 3 and R 4 being independently hydrogen, loweralkyl or arylloweralkyl; and R 2 is --CH 2 CH═CH 2 , ##STR2## R 5 and R 6 being independently loweralkyl or alternatively the group --NR 5 R 6 as a whole being ##STR3## R 7 being hydrogen, loweralkyl or arylloweralkyl; which are useful for enhancing cholinergic activity in mammals and hence for the treatment of various memory dysfunctions characterized by decreased cholinergic function such as Alzheimer's disease.
Inventors
- 👤 Lawrence L. Martin
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 16:14
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/18; C07D207/22; C07D207/24; C07D207/26; A; A61; A61P; A61P25/00; A61P25/28; C07D207/273; C07D207/277; C07D207/28
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
69 words
A compound of the formula ##STR16## where R 1 is loweralkoxycarbonyl or --CONR 3 R 4 , R 3 and R 4 being independently hydrogen, loweralkyl or arylloweralkyl; and R 2 is ##STR17## R 5 and R 6 being independently loweralkyl or alternatively the group --NR 5 R 6 as a whole being ##STR18## R 7 being hydrogen, loweralkyl or arylloweralkyl; or a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
69 words
A compound of the formula ##STR16## where R 1 is loweralkoxycarbonyl or --CONR 3 R 4 , R 3 and R 4 being independently hydrogen, loweralkyl or arylloweralkyl; and R 2 is ##STR17## R 5 and R 6 being independently loweralkyl or alternatively the group --NR 5 R 6 as a whole being ##STR18## R 7 being hydrogen, loweralkyl or arylloweralkyl; or a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
14 words
The compound as defined in claim 1, wherein R 1 is methoxycarbonyl or aminocarbonyl.
Claim 4
Dependent Claim
12 words
The compound as defined in claim 1, where R 2 is ##STR19##
Claim 5
Dependent Claim
26 words
The compound as defined in claim 3, wherein the group --NR 5 R 6 as a whole is ##STR20## R 7 being hydrogen, loweralkyl or arylloweralkyl.
Claim 6
Dependent Claim
14 words
The compound as defined in claim 3, where R 1 is methoxycarbonyl or aminocarbonyl.
Claim 7
Dependent Claim
14 words
The compound as defined in claim 4, where R 1 is methoxycarbonyl or aminocarbonyl.
Claim 8
Dependent Claim
10 words
The compound as defined in claim 1, which is 5-methoxycarbonyl-1-(2-propynyl)-2-pyrrolidinone.
Claim 9
Dependent Claim
11 words
The compound as defined in claim 1, which is 5-oxo-1-(2-propynyl)-2-pyrrolidine carboxamide.
Claim 10
Dependent Claim
11 words
The compound as defined in claim 1, which is 5-methoxycarbonyl-1-[4-(1-pyrrolidinyl)-2-butynyl]-2-pyrrolidinone oxalate.
Claim 11
Dependent Claim
11 words
The compound as defined in claim 1, which is 5-oxo-1-[4-(1-pyrrolidinyl)-2-butynyl]-2-pyrrolidine carboxamide.
Claim 12
Dependent Claim
10 words
The compound as defined in claim 1, which is 5-methoxycarbonyl-1-[4-(1-piperidinyl)-2-butynyl]-2-pyrrolidinone.
Claim 13
Dependent Claim
11 words
The compound as defined in claim 1, which is 5-oxo-1-[4-(1-piperidinyl)-2-butynyl]-2-pyrrolidine carboxamide.
Claim 14
Dependent Claim
10 words
The compound as defined in claim 1, which is 5-methoxycarbonyl-1-[4-(4-methyl-1-piperazinyl)-2-butynyl]-2-pyrrolidinone
Claim 15
Dependent Claim
11 words
The compound as defined in claim 1, which is 1-[4-(4-methyl-1-piperazinyl)-2-butynyl]-5-oxo-2-pyrrolidine carboxamide.
Claim 16
Dependent Claim
10 words
The compound as defined in claim 1, which is 5-methoxycarbonyl-1-[4-(1-morpholinyl)-2-butynyl]-2-pyrrolidinone.
Claim 17
Dependent Claim
11 words
The compound as defined in claim 1, which is 1-[4-(1-morpholinyl)-2-butynyl]-5-oxo-2-pyrrolidine carboxamide.
Claim 18
Dependent Claim
10 words
The compound as defined in claim 1, which is 1-(2-butynyl)-5-methoxycarbonyl-2-pyrrolidinone.
Claim 19
Dependent Claim
11 words
The compound as defined in claim 1, which is N-methyl-5-oxo-1-(2-propynyl)-2-pyrrolidine carboxamide.
Claim 20
Dependent Claim
11 words
The compound as defined in claim 1, which is N,N-dimethyl-5-oxo-1-(2-propynyl)-2-pyrrolidine carboxamide.
Claim 21
Dependent Claim
11 words
The compound as defined in claim 1, which is 5-oxo-N-phenylmethyl-1-(2-propynyl)-2-pyrrolidine carboxamide.
Claim 22
Dependent Claim
11 words
The compound as defined in claim 1, which is N,N-dimethyl-5-oxo-1-[4-(1-piperidinyl)-2-butynyl]-2-pyrrolidine carboxamide.
Claim 23
Dependent Claim
11 words
The compound as defined in claim 1, which is N-methyl-1-[4-(4-methyl-1-piperazinyl)-2-butynyl]-5-oxo-2-pyrrolidine carboxamide.
Claim 24
Dependent Claim
10 words
The compound as defined in claim 1, which is 5-methoxycarbonyl-1-[4-(4-phenylmethyl-1-piperazinyl)-2-butynyl]-2-pyrrolidinone.
Claim 25
Dependent Claim
11 words
The compound as defined in claim 1, which is N-methyl-5-oxo-1-[4-(4-phenylmethyl-1-piperazinyl)-2-butynyl]-2-pyrrolidine carboxamide.
Claim 26
Dependent Claim
30 words
A pharmaceutical composition which comprises a compound as defined in claim 1 in an amount effective for alleviating memory dysfunction characterized by decreased cholinergic function and a suitable carrier therefor.
Claim 27
Dependent Claim
30 words
A pharmaceutical composition which comprises a compound as defined in claim 3 in an amount effective for alleviating memory dysfunction characterized by decreased cholinergic function and a suitable carrier therefor.
Claim 28
Dependent Claim
30 words
A method of treating a pateint suffering from memory dysfunction characterized by decreased cholinergic function which comprises administering of an effective amount of a compound as defined in claim 1.
Claim 29
Dependent Claim
30 words
A method of treating a patient suffering from memory dysfunction characterized by decreased cholinergic function which comprises administering of an effective amount of a compound as defined in claim 3.
References Cited (Backward Citations)
US3444185A
Cited
US3565794A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-09-20 | 1992-03-21 | 1992-09-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-09-20 | 1996-03-21 | 1996-09-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-09-20 | 2000-03-21 | 2000-09-20 | $7700.00 | Window Closed / Lapsed |