Patent US4125530A successfully refreshed from Google Patents.
US4125530A
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Trifluoromethylimidazoles and a method for their preparation
Assignee: Merck and Co Inc
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Filing: 1977-02-02
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Granted: 1978-11-14
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Expires: 1997-02-02
Abstract
Abstract 4(5)-Trifluoromethylimidazoles having optional substituents in the 1 and 2 positions are provided. The novel 4(5)-trifluoromethylimidazoles are prepared by reacting a 1,1-dihalo-3,3,3-trifluoroacetone compound with an appropriate carboxaldehyde and ammonia. The 4(5)-trifluoromethylimidazoles are useful as anti-gout and anti-hyperuricemic agents.
Inventors
- 👤 John J. Baldwin
- 👤 Frederick C. Novello
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 08:31
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/54; C07D233/64; C07D233/66; C07D233/91; C07D233/92; C07D233/93; C07D233/94; C07D233/95
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
65 words
A process for preparing a compound of the formula: ##STR9## wherein R 2 is hydrogen, methyl, C 3 -c 5 alkyl, 2-dimethylaminoethyl, 1-dimethylamino-2-methyl-2-propyl, pyridyl, pyridyl-N-oxide, monomethylpyridyl, dimethylpyridyl, 6-quinolyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, pyrazinyl, methoxypyrazinyl, 4-chlorophenyl-4-pyrazolyl, 4-thiazolyl, phenyl, o-cyanophenyl, p-ethylphenyl, p-sulfamoylphenyl, p-N-methylsulfamoylphenyl, p-methoxyphenyl, 3-furyl, 2-thienyl, o-methoxyphenyl, p-acetylaminophenyl, p-cyanophenyl, p-dimethylaminophenyl, 5-indanyl, 1-indanyl, 3,4-dichlorophenyl, p-carboxyphenyl, 2-indanyl, 2-naphthyl, 1-naphthyl, monohalophenyl, p-methylsulfonamidophenyl, p-diethylaminoethoxyphenyl, diphenylmethyl, 1-methyl-4-pyrazolyl, p-nitrophenyl, 2-aminophenyl, 2-furyl, 2,4-dichlorophenyl, p-carboxyphenyl, monomethylphenyl,
Claim 2
Dependent Claim
65 words
A process for preparing a compound of the formula: ##STR9## wherein R 2 is hydrogen, methyl, C 3 -c 5 alkyl, 2-dimethylaminoethyl, 1-dimethylamino-2-methyl-2-propyl, pyridyl, pyridyl-N-oxide, monomethylpyridyl, dimethylpyridyl, 6-quinolyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, pyrazinyl, methoxypyrazinyl, 4-chlorophenyl-4-pyrazolyl, 4-thiazolyl, phenyl, o-cyanophenyl, p-ethylphenyl, p-sulfamoylphenyl, p-N-methylsulfamoylphenyl, p-methoxyphenyl, 3-furyl, 2-thienyl, o-methoxyphenyl, p-acetylaminophenyl, p-cyanophenyl, p-dimethylaminophenyl, 5-indanyl, 1-indanyl, 3,4-dichlorophenyl, p-carboxyphenyl, 2-indanyl, 2-naphthyl, 1-naphthyl, monohalophenyl, p-methylsulfonamidophenyl, p-diethylaminoethoxyphenyl, diphenylmethyl, 1-methyl-4-pyrazolyl, p-nitrophenyl, 2-aminophenyl, 2-furyl, 2,4-dichlorophenyl, p-carboxyphenyl, monomethylphenyl,
Claim 3
Dependent Claim
39 words
4-methylenedioxyphenyl, p-isopropylphenyl, 3,4-dimethoxyphenyl, p-N,N-dimethylsulfamoylphenyl, p-methylaminophenyl, 2,6-dimethyl-4-pyridyl, 4,6-dimethyl-2-pyridyl, pyrazinyl, m-methoxymethoxyphenyl, p-diethylaminoethoxyphenyl, 1-benzyl-4-pyrazolyl, 1-phenyl-4-pyrazolyl, 1-methyl-4-pyrazolyl, and 1-piperidino-2-methyl-2-propyl which comprises the steps of (a) treating 1,1-dihalo-3,3,3-trifluroacetone with a base and then (b) treating the resulting mixture with ammonia and the appropriate carboxaldehyde.
Claim 4
Dependent Claim
39 words
4-methylenedioxyphenyl, p-isopropylphenyl, 3,4-dimethoxyphenyl, p-N,N-dimethylsulfamoylphenyl, p-methylaminophenyl, 2,6-dimethyl-4-pyridyl, 4,6-dimethyl-2-pyridyl, pyrazinyl, m-methoxymethoxyphenyl, p-diethylaminoethoxyphenyl, 1-benzyl-4-pyrazolyl, 1-phenyl-4-pyrazolyl, 1-methyl-4-pyrazolyl, and 1-piperidino-2-methyl-2-propyl which comprises the steps of (a) treating 1,1-dihalo-3,3,3-trifluroacetone with a base and then (b) treating the resulting mixture with ammonia and the appropriate carboxaldehyde.
Claim 5
Dependent Claim
28 words
The process of claim 1 wherein the product thus obtained is treated with 1,2-epoxyethane or 1,3-epoxypropane in the presence of a Lewis acid to afford the corresponding 1-hydroxyalkyl-4(5)-trifluoromethylimidazole.
Claim 6
Dependent Claim
22 words
The process according to claim 1 wherein R 2 is said naphthyl, alkyl, quinolyl, thiazolyl, furyl, thienyl, pyrazinyl or substituted phenyl group.
Claim 7
Dependent Claim
33 words
The process of claim 1 wherein 1,1-dibromo-3,3,3-trifluoroacetone is treated with sodium acetate trihydrate at 80°-100° C., and the resulting mixture is treated with 2,3,4-or 6- quinolinecarboxaldehyde and ammonia to afford the corresponding 2-(quinolyl)-4(5)-trifluoromethylimidazole.
Claim 8
Dependent Claim
29 words
The process of claim 1 wherein 1,1-dibromo-3,3,3-trifluoroacetone is treated with sodium acetate trihydrate at 80°-100° C., and the resulting mixture is treated with p-chlorobenzenecarboxaldehyde and ammonia to afford 2-(p-chlorophenyl)-4(5)-trifluoromethylimidazole.
Claim 9
Dependent Claim
29 words
The process of claim 1 wherein 1,1-dibromo-3,3,3-trifluoroacetone is treated with sodium acetate trihydrate at 80°-100° C, and the resulting mixture is treated with 4-thiazolecarboxaldehyde and ammonia to afford 2-(4-thiazolyl)-4(5)-trifluoromethylimidazole.
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) | 1981-11-13 | 1982-05-15 | 1982-11-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-11-13 | 1986-05-15 | 1986-11-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-11-13 | 1990-05-15 | 1990-11-14 | $7700.00 | Window Closed / Lapsed |