Patent US4826843A successfully refreshed from Google Patents.
US4826843A
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Cerebral function enhancing diazinylpiperidine derivatives
Assignee: Bristol Myers Co
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Filing: 1987-08-28
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Granted: 1989-05-02
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Expires: 2007-08-28
Abstract
Abstract A series of diazinylpiperidine compounds of Formula I ##STR1## wherein X is an ethylene chain or a 1,2-benzo ring; Y is carbonyl or methylene; R 1 is hydrogen or lower alkyl; and Z is an R 2 , R 3 -disubstituted diazinyl ring selected from pyridazine, pyrimidine, and pyrazine ring systems. Pharmacologic and neuroanatomical testing demonstrates that compounds of the series act to enhance cerebral function in mammals, particularly when there is a deficit in normal cerebral functioning. Specific pharmacologic test results indicate that compounds of Formula I possess cognition and memory enhancing activity.
Inventors
- 👤 Ronald J. Mattson
- 👤 Joseph P. Yevich
- 👤 Michael S. Eison
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-10 02:24
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/14
Claims Analysis
Total Claims: 37
Claim 1
Independent Claim
124 words
A compound selected from the group of 1,2-, 1,3-, and 1,4-disubstituted piperidine of Formula I ##STR43## wherein X is an ethylene chain or a 1,2-benzo ring; Y is a carbonyl group or -CH 2 -, with the proviso that Y is carbonyl only when X is a 1,2-benzo ring; R 1 is selected from hydrogen or C 1-4 alkyl; and Z is an R 2 -, R 3 - disubstituted diazine bonded through a carbon atom thereof and selected from pyrimidine, pyridazine and pyrazine, with R 2 and R 3 being independently chosen from hydrogen,lower (C 1-4 ) alkyl, lower alkoxy, lower alkylthio, cyano, trifluoromethyl, pentafluorethyl, and halogen and connected at carbon atoms of the diazine; and the pharmaceutically acceptable acid addition salts thereof.
Claim 2
Dependent Claim
124 words
A compound selected from the group of 1,2-, 1,3-, and 1,4-disubstituted piperidine of Formula I ##STR43## wherein X is an ethylene chain or a 1,2-benzo ring; Y is a carbonyl group or -CH 2 -, with the proviso that Y is carbonyl only when X is a 1,2-benzo ring; R 1 is selected from hydrogen or C 1-4 alkyl; and Z is an R 2 -, R 3 - disubstituted diazine bonded through a carbon atom thereof and selected from pyrimidine, pyridazine and pyrazine, with R 2 and R 3 being independently chosen from hydrogen,lower (C 1-4 ) alkyl, lower alkoxy, lower alkylthio, cyano, trifluoromethyl, pentafluorethyl, and halogen and connected at carbon atoms of the diazine; and the pharmaceutically acceptable acid addition salts thereof.
Claim 3
Dependent Claim
14 words
A compound of claim 1 wherein X is ethylene and R 1 is hydrogen.
Claim 4
Dependent Claim
19 words
A compound of claim 1 wherein R 2 and R 3 are independently selected from hydrogen, halogen, and trifluoromethyl.
Claim 5
Dependent Claim
19 words
A compound of claim 2 wherein R 2 and R 3 are independently selected from hydrogen, halogen, and trifluoromethyl.
Claim 6
Dependent Claim
6 words
The compound of claim 1, 2-[[1-(2-pyrimidinyl)-4-piperidinyl]methyl]-1H-isoindole-1,3-(2H)-dione.
Claim 7
Dependent Claim
6 words
The compound of claim 1, 1-[[1-(2-pyrimidinyl)-4-piperidinyl)]methyl]-2-pyrrolidinone.
Claim 8
Dependent Claim
7 words
The compound of claim 1, 1-[[1-(2-chloro-4-pyrimidinyl) -4-piperidinyl]-methyl]-2-pyrrolidinone.
Claim 9
Dependent Claim
7 words
The compound of claim 1, 1-[[1-(4-chlro-2-pyrimidinyl) -4-piperidinyl]methyl]-2-pyrrolidinoine.
Claim 10
Dependent Claim
6 words
The compound of claim 1, 1-[[1-(6-chloro-2pyrazinyl)-4--piperidinyl]-methyl]-2-pyrrolidinone.
Claim 11
Dependent Claim
6 words
The compound of claim 1, 1-[[1-[2-(trifluoromethyl)-4-pyrimidinyl]methyl]-2-pyrrolidinone.
Claim 12
Dependent Claim
6 words
The compound of claim 1, 1-[[1-(2-pyrimidinyl)-3-piperidinyl]methyl]-2-pyrrolidinone.
Claim 13
Dependent Claim
6 words
The compound of claim 1, 1-[[1-2-pyrimidinyl)-2-piperidinyl]methyl]-2-pyrrolidinone.
Claim 14
Dependent Claim
6 words
The compound of claim 1, 1-[[1-(6-chloro-3-pyridazinyl)-4-piperidinyl]-methyl]-2-pyrrolidinone.
Claim 15
Dependent Claim
6 words
The compound of claim 1, 1-[[1-(5-fluoro-4-(methylthio)-2-pyrimidinyl]-4-piperidinyl]methyl]-2pyrrolidininone.
Claim 16
Dependent Claim
5 words
The compound of claim 1,1-[[1-(5-fluro-2-pyrimidinyl)-4-piperidinyl]-methyl]-2-pyrrolidinone.
Claim 17
Dependent Claim
7 words
The compound of claim 1, 1-[[1-(2,6-dichloro-4-pyrimidinyl4-piperid815 inyl]-methyl]-2-pyrrolidinone.
Claim 18
Dependent Claim
6 words
The compound of claim 1, 1-[[1-(4,6-dichloro-2-pyrimidinyl)-4-piperidinyl]methyl]-2-pyrrolidinone.
Claim 19
Dependent Claim
7 words
The compound of claim 1, 1-[[1-(6-chloro-4-pyrimidinyl)-b 4-piperidinyl]methyl]-2-pyrrolidinone.
Claim 20
Dependent Claim
6 words
The compound of claim 1, 1-[[1-(2-chloro-6-methyl-4-pyrimidinyl)-4-piperidinyl]methyl]-2-pyrrolidinone.
Claim 21
Dependent Claim
6 words
The compound of claim 1, 1-[[1-(4-chloro-6-methyl-2-pyrimidinyl)4-piperidinyl]methyl]-2-pyrrolidinone.
Claim 22
Dependent Claim
6 words
The compound of claim 1, 1[[1]-(5-bromo-2-pyrimidinyl)-4-piperidinyl]methyl]-2-pyrrolidinone.
Claim 23
Dependent Claim
7 words
The compound of claim 1, 1-[[1-(5-chloro-2-pyrimidinyl) -4-piperidinyl]methyl]-2-pyrrolidinone.
Claim 24
Dependent Claim
6 words
The compound of claim 1, 1[[-(5-iodo-2-pyrimidinyl)-4-piperidinyl]methyl]-2-pyrrolidinone.
Claim 25
Dependent Claim
6 words
The compound of claim 1, 1-[[1-(6-chloro-2-(methylthio)-4-pyrimidinyl]-4-piperdinyl]methyl]-2-pyrrolidinone.
Claim 26
Dependent Claim
7 words
The compound of claim 1, 1-[[1-(5,6-dichloro -4-pyridazinyl)-4-piperidinyl]methyl]-2-pyrrolidinone.
Claim 27
Dependent Claim
6 words
The compound of claim 1, 1-[[1-(5-bromo-2-chloro-4-pyrimidinyl)-4-piperidinyl]methyl]-2-pyrrolidinone.
Claim 28
Dependent Claim
6 words
The compound of claim 1, 1-[[1-(2-methyoxy-4-pyrimidinyl)-4-piperidinyl]methyl]-2-pyrrolidinone.
Claim 29
Dependent Claim
6 words
The compound of claim 1, 4-]4-(2-oxopyrrolidin-1-yl)methyl]-1-piperidinyl]-2-pyrimidine-carbonitrile.
Claim 30
Dependent Claim
7 words
The compound of claim 1, 1-[[1-]2-(pentafluoroethyl) -4-pyrimidinyl]-4-piperidinyl]methyl]2-pyrrolidinone.
Claim 31
Dependent Claim
6 words
The compound of claim 1, 1-[[1-[5-chloro-2-(trifluromethyl)-4-pyrimdinyl]-4-piperidinyl]methyl]2-pyrrolidinone.
Claim 32
Dependent Claim
6 words
The compound of claim 1, 1-[[1-[2,6-bis-trifluoromethyl)-4-pyurimidinyl]-4-piperidinyl]methyl]-2-pyrrolidinone.
Claim 33
Dependent Claim
7 words
The compound of claim 1, 1-[[1-(6-chloro-3-pyridazinyl) -4-piperidinyl]methhyl]-2-pyrrolidinone.
Claim 34
Dependent Claim
31 words
The method for enhancing cerebral function in a mammal in need of such treatment which comprises systemic administration to the mammal of an effective dose a compound claimed in claim 1.
Claim 35
Dependent Claim
54 words
The method for treating a disorder in a mammal in need of such treatment, the disorder selected from the group consisting of dementia, amnesia, failing memory, learning disability, mild retardation, dyslexia, aphasia, and Tourette's syndrome; the treatment comprising systemic administration to the mammal of an effective dose of a compound claimed in claim 1.
Claim 36
Dependent Claim
12 words
A compound of claim 1 comprising a 1,4-disubstituted piperidine of formula I.
Claim 37
Dependent Claim
20 words
A pharmaceutical composition for the enhancement of cerebral function comprising a pharmaceutical carrier and a compound according to claim 1.
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) | 1992-05-01 | 1992-10-31 | 1993-05-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-05-01 | 1996-10-31 | 1997-05-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-05-01 | 2000-10-31 | 2001-05-02 | $7700.00 | Window Closed / Lapsed |