US4236005A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Imidazo[1,5-a]pyrimidines
Assignee: Wyeth Holdings LLC
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Filing: 1979-07-02
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Granted: 1980-11-25
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Expires: 1999-07-02
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
2026-10-31 18:47
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/14; C07D231/38; C07D471/00; C07D471/02; C07D471/04
Claims Analysis
Total Claims: 11
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; 4-(α,α,α-trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine-8-carbonitrile.
Claim 4
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 ethoxy carbonyl; ethyl 4-(α,α,α-trifluoro-n-tolyl)imidazo(1,5-a]pyrimidine-8-carboxylate.
Claim 5
Dependent Claim
24 words
The compound according to claim 1 wherein R 1 , R 3 and R 4 are hydrogen and R 2 is m-trifluoromethylphenyl; 4-(α, α,α-trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine.
Claim 6
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 hydroxymethyl; 4-(α,α,α-trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine-8-methanol.
Claim 7
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 methyl; 8-methyl-4-(α,α,α-trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine.
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; 8-(methoxymethyl)-4-(α,α,α-trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine.
Claim 9
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 4-(α,α,α-trifluoro-m-tolyl)imidazo[1,5-a]pyrimidin-8-yl ketone.
Claim 10
Dependent Claim
25 words
The compound according to claim 1 wherein R 1 is hydrogen, R 3 is methyl, R 2 is m-trifluoromethylphenyl and R 4 is cyano; 2-methyl-4-(α,α,α-trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine-8-carbonitrile.
Claim 11
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; 8-bromo-4-(α,α,α-trifluoro-m-tolyl)imidazo[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) | 1983-11-25 | 1984-05-26 | 1984-11-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-11-25 | 1988-05-26 | 1988-11-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-11-25 | 1992-05-26 | 1992-11-25 | $7700.00 | Window Closed / Lapsed |