US4178449A
Expired / Lapsed
US
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Pyrazolo[1,5-a]pyrimidines and imidazo-[1,5-a]pyrimidines
Assignee: Wyeth Holdings LLC
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Filing: 1978-12-15
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Granted: 1979-12-11
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Expires: 1998-12-15
Abstract
Abstract This disclosure describes substituted pyrazolo[1,5-a]pyrimidines and imidazo[1,5-a]pyrimidines which possess anxiolytic activity.
Inventors
- 👤 John P. Dusza
- 👤 Jay D. Albright
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 00:48
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/14; C07D231/38; C07C; C07C45/00; C07C45/61; C07C45/67; C07C45/68; C07D487/00; C07D487/02; C07D487/04
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
93 words
A compound of the formula: ##STR6## wherein R 1 is hydrogen or alkyl having up to 3 carbon atoms; R 2 is selected from the group consisting of phenyl, o-trifluoromethylphenyl, m-trifluoromethylphenyl and m-methoxyphenyl; R 3 is hydrogen, fluoro, chloro, bromo, cyano, cyanomethyl, carbamoyl or alkyl having up to 3 carbon atoms; and R 4 is selected from the group consisting of hydrogen, fluoro, chloro, bromo, formyl, carboxyl, cyano, hydroxymethyl, N-hydroxyformimidoyl, alkyl having up to 3 carbon atoms and moieties of the formulae: ##STR7## wherein R is alkyl having up to 3 carbon atoms.
Claim 2
Dependent Claim
93 words
A compound of the formula: ##STR6## wherein R 1 is hydrogen or alkyl having up to 3 carbon atoms; R 2 is selected from the group consisting of phenyl, o-trifluoromethylphenyl, m-trifluoromethylphenyl and m-methoxyphenyl; R 3 is hydrogen, fluoro, chloro, bromo, cyano, cyanomethyl, carbamoyl or alkyl having up to 3 carbon atoms; and R 4 is selected from the group consisting of hydrogen, fluoro, chloro, bromo, formyl, carboxyl, cyano, hydroxymethyl, N-hydroxyformimidoyl, alkyl having up to 3 carbon atoms and moieties of the formulae: ##STR7## wherein R is alkyl having up to 3 carbon atoms.
Claim 3
Dependent Claim
24 words
The compound according to claim 1 wherein R 1 and R 3 are hydrogen, R 2 is m-trifluoromethylphenyl and R 4 is cyano; 7-(α,α,α-trifluoro-m-tolyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile.
Claim 4
Dependent Claim
25 words
The compound according to claim 1 wherein R 1 and R 3 are hydrogen; R 2 is m-trifluoromethylphenyl and R 4 is ethoxycarbonyl; ethyl 7-(α,α,α-trifluoro-m-tolyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate.
Claim 5
Dependent Claim
26 words
The compound according to claim 1 wherein R 1 and R 3 are hydrogen; R 2 is m-trifluoromethylphenyl and R 4 is acetyl; methyl 7-(α,α,α-trifluoro-m-tolyl)pyrazolo[1,5-a]pyrimidin-3-yl ketone.
Claim 6
Dependent Claim
25 words
The compound according to claim 1 wherein R 1 and R 3 are hydrogen, R 2 is m-trifluoromethylphenyl and R 4 is N-hydroxyformimidoyl; 7-(α,α,α-trifluoro-m-tolyl)pyrazolo[1,5-a]-pyrimidine-3-carboxaldehyde oxime.
Claim 7
Dependent Claim
25 words
The compound according to claim 1 wherein R 1 and R 3 are hydrogen; R 2 is m-methoxyphenyl and R 4 is cyano; 7-(m-methyoxyphenyl) pyrazolo[1,5-a]pyrimidine-3-carbonitrile.
Claim 8
Dependent Claim
24 words
The compound according to claim 1 wherein R 1 and R 3 are hydrogen; R 2 is m-trifluoromethylphenyl and R 4 is methoxymethyl; 3-(methoxymethyl)-7-(α,α,α-trifluoro-m-tolyl)pyrazolo-[1,5-a]pyrimidine.
Claim 9
Dependent Claim
24 words
The compound according to claim 1 wherein R 1 and R 3 are hydrogen; R 2 is m-trifluoromethylphenyl and R 4 is bromo; 3-bromo-7-(α,α,α-trifluoro-m-tolyl)pyrazolo[1,5-a]pyrimidine.
Claim 10
Dependent Claim
24 words
The compound according to claim 1 wherein R 1 is hydrogen; R 2 is m-trifluoromethylphenyl and R 3 and R 4 are cyano; 2-cyano-7(α,α,α-trifluoro-m-tolyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile.
Claim 11
Dependent Claim
25 words
The compound according to claim 1 wherein R 1 is hydrogen, R 2 is m-trifluoromethylphenyl, R 3 is cyanomethyl, and R 4 is cyano; 3-cyano-7-(α,α,α-trifluoro-m-tolyl)pyrazolo[1,5-a]-pyrimidine-2-acetonitrile.
Claim 12
Dependent Claim
23 words
The compound according to claim 1 wherein R 1 and R 3 are hydrogen, R 2 is m-trifluoromethylphenyl, R 4 is methyl; 3-methyl-7-(α,α,α-trifluoro-m-tolyl)pyrazolo[1,5-a]pyrimidine.
Claim 13
Dependent Claim
2 words
Ethyl 7-(m-tolyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate.
Claim 14
Dependent Claim
2 words
Ethyl 7-(m-tolyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate.
Claim 15
Dependent Claim
2 words
Ethyl 7-(3,4-xylyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate.
Claim 16
Dependent Claim
2 words
Ethyl 7-(3,4-xylyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate.
Claim 17
Dependent Claim
2 words
Ethyl 7(p-ethylphenyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate.
Claim 18
Dependent Claim
2 words
Ethyl 7(p-ethylphenyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate.
Claim 19
Dependent Claim
2 words
Ethyl 7-(3,4-dimethoxyphenyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate.
Claim 20
Dependent Claim
2 words
Ethyl 7-(3,4-dimethoxyphenyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate.
Claim 21
Dependent Claim
1 words
7-(m-Fluorophenyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile.
Claim 22
Dependent Claim
1 words
7-(m-Fluorophenyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile.
Claim 23
Dependent Claim
1 words
5-Phenylpyrazolo[1,5-a]pyrimidine.
Claim 24
Dependent Claim
1 words
5-Phenylpyrazolo[1,5-a]pyrimidine.
Claim 25
Dependent Claim
1 words
5-(α,α,α-Trifluoro-m-tolyl)pyrazolo[1,5-a]pyrimidine.
Claim 26
Dependent Claim
1 words
5-(α,α,α-Trifluoro-m-tolyl)pyrazolo[1,5-a]pyrimidine.
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) | 1982-12-10 | 1983-06-11 | 1983-12-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-12-10 | 1987-06-11 | 1987-12-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-12-10 | 1991-06-11 | 1991-12-11 | $7700.00 | Window Closed / Lapsed |