US4521422A
Expired / Lapsed
US
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Aryl and heteroaryl[7-(aryl and heteroaryl)pyrazolo[1,5-a]pyrimidin-3-yl]methanones
Assignee: Wyeth Holdings LLC
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Filing: 1984-05-24
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Granted: 1985-06-04
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Expires: 2004-05-24
Abstract
Abstract Aryl and heteroaryl[7-(aryl and heteroaryl)pyrazolo[1,5-a]pyrimidin-3-yl]methanones which are new compounds active as anxiolytic, anticonvulsant, sedative-hypnotic and skeletal muscle relaxant agents in mammals and the novel process of making these compounds.
Inventors
- 👤 John P. Dusza
- 👤 Andrew S. Tomcufcik
- 👤 Jay D. Albright
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 22:15
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/04
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
197 words
A compound selected from those of the formula: ##STR12## wherein R 1 is selected from the group consisting of unsubstituted phenyl; phenyl mono- or di-substituted by halogen, alkoxy(C 1 -C 3 ) or alkyl(C 1 -C 3 ); phenyl mono-substituted by trifluoromethyl, alkylthio(C 1 -C 3 ), alkylamino(C 1 -C 3 ), dialkylamino(C 1 -C 3 ), methylenedioxy, alkylsulfonyl(C 1 -C 3 ) or alkanoylamino(C 1 -C 3 ); naphthalenyl; thiazolyl; biphenyl; thienyl; furanyl; pyridinyl; substituted thiazolyl; substituted biphenyl; substituted thienyl; and substituted pyridinyl wherein the substituents are selected from one or two of the group consisting of halogen, alkoxy(C 1 -C 3 ) and alkyl(C 1 -C 3 ); R 2 , R 4 and R 5 are each selected from the group consisting of hydrogen and alkyl(C 1 -C 3 ); and R 3 is selected from the group consisting of unsubstituted phenyl, phenyl mono-substituted by halogen, trifluoromethyl, alkoxy(C 1 -C 3 ), amino, alkyl(C 1 -C 3 ), alkylamino(C 1 -C 6 ), dialkylamino(C 1 -C 3 ), alkanoylamino(C 1 -C 6 ), N-alkyl(C 1 -C 6 )alkanoylamino(C 1 -C 6 ), cyano or alkylthio(C 1 -C 3 ); furanyl; thienyl; pyridinyl; and pyridine-1-oxide.
Claim 2
Dependent Claim
197 words
A compound selected from those of the formula: ##STR12## wherein R 1 is selected from the group consisting of unsubstituted phenyl; phenyl mono- or di-substituted by halogen, alkoxy(C 1 -C 3 ) or alkyl(C 1 -C 3 ); phenyl mono-substituted by trifluoromethyl, alkylthio(C 1 -C 3 ), alkylamino(C 1 -C 3 ), dialkylamino(C 1 -C 3 ), methylenedioxy, alkylsulfonyl(C 1 -C 3 ) or alkanoylamino(C 1 -C 3 ); naphthalenyl; thiazolyl; biphenyl; thienyl; furanyl; pyridinyl; substituted thiazolyl; substituted biphenyl; substituted thienyl; and substituted pyridinyl wherein the substituents are selected from one or two of the group consisting of halogen, alkoxy(C 1 -C 3 ) and alkyl(C 1 -C 3 ); R 2 , R 4 and R 5 are each selected from the group consisting of hydrogen and alkyl(C 1 -C 3 ); and R 3 is selected from the group consisting of unsubstituted phenyl, phenyl mono-substituted by halogen, trifluoromethyl, alkoxy(C 1 -C 3 ), amino, alkyl(C 1 -C 3 ), alkylamino(C 1 -C 6 ), dialkylamino(C 1 -C 3 ), alkanoylamino(C 1 -C 6 ), N-alkyl(C 1 -C 6 )alkanoylamino(C 1 -C 6 ), cyano or alkylthio(C 1 -C 3 ); furanyl; thienyl; pyridinyl; and pyridine-1-oxide.
Claim 3
Dependent Claim
36 words
A compound according to claim 1, wherein R 1 is 2-furanyl; R 2 , R 4 and R 5 are each hydrogen; and R 3 is selected from the group consisting of 3-(trifluoromethyl)phenyl; 3-pyridinyl; and 4-pyridinyl.
Claim 4
Dependent Claim
71 words
A compound according to claim 1, wherein R 1 is selected from the group consisting of unsubstituted phenyl; phenyl substituted by 4-methyl, 4-ethyl, 4-methoxy, 3,4-dimethoxy or 4-dimethylamino; 2-furanyl; 2-thienyl; 2-pyridinyl; and 4-pyridinyl; R 2 , R 4 and R 5 are each hydrogen; and R 3 is selected from the group consisting of 3-(trifluoromethyl)phenyl; 3-pyridinyl; 4-pyridinyl; 3-[N-alkyl(C 1 -C 6 )alkanoylamino(C 1 -C 6 )]phenyl; and 3-[alkylamino(C 1 -C 6 )].
Claim 5
Dependent Claim
7 words
The compound according to claim 1, phenyl[7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone.
Claim 6
Dependent Claim
7 words
The compound according to claim 1, (4-fluorophenyl)[7-(4-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]-methanone.
Claim 7
Dependent Claim
7 words
The compound according to claim 1, phenyl[7-(4-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone.
Claim 8
Dependent Claim
7 words
The compound according to claim 1, phenyl[7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]methanone.
Claim 9
Dependent Claim
7 words
The compound according to claim 1, (4-methoxyphenyl)[7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone.
Claim 10
Dependent Claim
7 words
The compound according to claim 1, (3-fluorophenyl)[7-(4-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone.
Claim 11
Dependent Claim
7 words
The compound according to claim 1, [7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl][3-(trifluoromethyl)phenyl]methanone.
Claim 12
Dependent Claim
7 words
The compound according to claim 1, 2-thienyl[7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]methanone.
Claim 13
Dependent Claim
7 words
The compound according to claim 1, 2-furanyl[7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]methanone.
Claim 14
Dependent Claim
7 words
The compound according to claim 1, 2-furanyl[7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone.
Claim 15
Dependent Claim
7 words
The compound according to claim 1, [2-methyl-7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]phenylmethanone.
Claim 16
Dependent Claim
7 words
The compound according to claim 1, (4-methylphenyl)[7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone.
Claim 17
Dependent Claim
8 words
The compound according to claim 1, phenyl[7-(4-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone, pyridine-1-oxide.
Claim 18
Dependent Claim
7 words
The compound according to claim 1, 2-pyridinyl[7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone.
Claim 19
Dependent Claim
7 words
The compound according to claim 1, 2-pyridinyl[7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]methanone.
Claim 20
Dependent Claim
7 words
The compound according to claim 1, 2-pyridinyl[7-(4-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone.
Claim 21
Dependent Claim
7 words
The compound according to claim 1, [7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]-2-thiazolyl-methanone.
Claim 22
Dependent Claim
7 words
The compound according to claim 1, 4-pyridinyl[7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone.
Claim 23
Dependent Claim
7 words
The compound according to claim 1, 4-pyridinyl[7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]methanone.
Claim 24
Dependent Claim
7 words
The compound according to claim 1, (2-fluorophenyl)[7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone.
Claim 25
Dependent Claim
7 words
The compound according to claim 1, (2-fluorophenyl)[7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]methanone.
Claim 26
Dependent Claim
7 words
The compound according to claim 1, [7-[3-(ethylamino)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]-2-furanylmethanone
Claim 27
Dependent Claim
7 words
The compound according to claim 1, [7-[3-(ethylamino)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]phenylmethanone.
Claim 28
Dependent Claim
27 words
A method of meliorating anxiety in a mammal suffering from anxiety which comprises administering to said mammal an effective anxiolytic amount of a compound of claim 1.
Claim 29
Dependent Claim
27 words
A method of treating epilepsy in a mammal suffering from epilepsy which comprises administering to said mammal an effective anticonvulsant amount of a compound of claim 1.
Claim 30
Dependent Claim
28 words
A method of inducing sedation or hypnosis in a mammal which comprises administering to said mammal an effective sedative or hypnotic amount of a compound of claim 1.
Claim 31
Dependent Claim
28 words
A method of inducing skeletal muscle relaxation in a mammal which comprises administering to said mammal an effective skeletal muscle relaxant amount of a compound of claim 1.
Claim 32
Dependent Claim
25 words
A composition of matter in dosage unit form comprising from 2-750 mg of a compound of claim 1 in association with a pharmaceutically acceptable carrier.
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) | 1988-06-03 | 1988-12-03 | 1989-06-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-06-03 | 1992-12-03 | 1993-06-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-06-03 | 1996-12-03 | 1997-06-04 | $7700.00 | Window Closed / Lapsed |