US4159338A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Antiinflammatory-4,5-dicyclic-2-(substituted thio)-imidazoles and their corresponding sulfoxides and sulfones
Assignee: EIDP Inc
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Filing: 1978-01-05
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Granted: 1979-06-26
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Expires: 1998-01-05
Abstract
Abstract Antiinflammatory 4,5-dicyclic-2-(substituted thio)-imidazoles and their corresponding sulfoxides and sulfones, such as, 4-(4-fluorophenyl)-2-(1,1,2,2-tetrafluoroethylsulfonyl)-5-(2-thienyl)- 1H-imidazole, useful for treating arthritis and related diseases.
Inventors
- 👤 Saul C. Cherkofsky
- 👤 Thomas R. Sharpe
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 18:25
CPC Classifications
C; C07; C07D; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/24; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/44; C07D213/46; C07D213/50; C07D231/00; C07D231/02; C07D231/10; C07D231/14; C07D231/18; C07D333/22
Claims Analysis
Total Claims: 40
Claim 1
Independent Claim
193 words
A compound of the formula ##STR55## where n=0, 1, or 2; R 1 =polyfluoro-C 1 --C 2 alkyl; R 2 and R 3 , the same or different=2-thienyl, 3-thienyl, 3-pyridyl, 3-pyridyl-N→oxide, 2-furyl or ##STR56## where Y 1 and Y 2 , the same or different=H, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, Cl, F, or Y 1 and Y 2 taken together forming a dioxymethylene bridge, provided that only one of R 2 or R 3 can= ##STR57## and R 4 =hydrogen; ##STR58## 2-tetrahydropyranyl, 2-tetrahydrofuranyl, ##STR59## or --SO 2 Ar; where R 5 =h or methyl; R 6 =c 1 -c 3 alkyl, benzyl, --CH 2 CH 2 OCH 3 ##STR60## R 7 =C 1 -C 4 alkyl or benzyl; and ##STR61## where Y 3 =H, F, Cl, Br, C 1 -C 4 alkyl C 1 -C 4 alkoxy or nitro; provided when ##STR62## or --SO 2 Ar, then n must be 0; or its pharmaceutically suitable acid addition salt where n=0 or where at least one of R 2 or R 3 , independently, =3-pyridyl or its pharmaceutically suitable metal salt where R 4 =hydrogen and n=1 or 2.
Claim 2
Dependent Claim
193 words
A compound of the formula ##STR55## where n=0, 1, or 2; R 1 =polyfluoro-C 1 --C 2 alkyl; R 2 and R 3 , the same or different=2-thienyl, 3-thienyl, 3-pyridyl, 3-pyridyl-N→oxide, 2-furyl or ##STR56## where Y 1 and Y 2 , the same or different=H, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, Cl, F, or Y 1 and Y 2 taken together forming a dioxymethylene bridge, provided that only one of R 2 or R 3 can= ##STR57## and R 4 =hydrogen; ##STR58## 2-tetrahydropyranyl, 2-tetrahydrofuranyl, ##STR59## or --SO 2 Ar; where R 5 =h or methyl; R 6 =c 1 -c 3 alkyl, benzyl, --CH 2 CH 2 OCH 3 ##STR60## R 7 =C 1 -C 4 alkyl or benzyl; and ##STR61## where Y 3 =H, F, Cl, Br, C 1 -C 4 alkyl C 1 -C 4 alkoxy or nitro; provided when ##STR62## or --SO 2 Ar, then n must be 0; or its pharmaceutically suitable acid addition salt where n=0 or where at least one of R 2 or R 3 , independently, =3-pyridyl or its pharmaceutically suitable metal salt where R 4 =hydrogen and n=1 or 2.
Claim 3
Dependent Claim
17 words
A compound of claim 1 where R 1 =--CF 2 CF 2 H or --CF 3 .
Claim 4
Dependent Claim
15 words
A compound of claim 1 where R 2 and R 3 , independently=2-thienyl or 3-pyridyl.
Claim 5
Dependent Claim
20 words
A compound of claim 1 where R 2 or ##STR63## where Y 1 =H, Cl, F, or CH 3 O.
Claim 6
Dependent Claim
15 words
A compound of claim 1 where R 4 =hydrogen, ethoxycarbonyl, benzyloxymethyl, acetyl, benzoyl or 2-tetrahydrofuranyl.
Claim 7
Dependent Claim
9 words
A compound of claim 4 where R 4 =hydrogen.
Claim 8
Dependent Claim
58 words
A compound of claim 1 where R 1 =--CF 2 CF 2 H or --CF 3 ; R 2 and R 3 , independently,=2-thienyl, or 3-pyridyl, or ##STR64## where Y 1 =H, Cl, F or CH 3 O, provided that only one of R 2 or R 3 ##STR65## and R 4 =hydrogen, benzyloxymethyl, acetyl, benzoyl, or 2-tetrahydrofuranyl.
Claim 9
Dependent Claim
8 words
The compound of claim 1 which is 4-(4-fluoro-phenyl)-2-(1,1,2,2-tetrafluoroethylsulfonyl)-5-(2-thienyl)-1H-imidazole.
Claim 10
Dependent Claim
8 words
The compound of claim 1 which is 4-(4-fluorophenyl)-5-(2-thienyl)-2-trifluoromethylsulfonyl-1H-imidazole.
Claim 11
Dependent Claim
8 words
The compound of claim 1 which is 4-(4-methoxyphenyl)-4-(2-thienyl)-2-trifluoromethylsulfonyl-1H-imidazole.
Claim 12
Dependent Claim
8 words
The compound of claim 1 which is 4,5-bis-(2-thienyl)-2-(1,1,2,2-tetrafluoroethylsulfonyl)-1H-imidazole.
Claim 13
Dependent Claim
8 words
The compound of claim 1 which is 4-(4-methoxyphenyl)-2-(1,1,2,2-tetrafluoroethylsulfonyl)-5-(2-thienyl)-1H-imidazole.
Claim 14
Dependent Claim
8 words
The compound of claim 1 which is 4-(3,4-dichlorophenyl)-2-(1,1,2,2-tetrafluoroethylsulfonyl)-5-(2-thienyl)-1H-imidazole.
Claim 15
Dependent Claim
19 words
A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective antiarthritic amount of the compound of claim 1.
Claim 16
Dependent Claim
19 words
A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective antiarthritic amount of the compound of claim 2.
Claim 17
Dependent Claim
19 words
A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective antiarthritic amount of the compound of claim 3.
Claim 18
Dependent Claim
19 words
A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective antiarthritic amount of the compound of claim 4.
Claim 19
Dependent Claim
19 words
A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective antiarthritic amount of the compound of claim 5.
Claim 20
Dependent Claim
19 words
A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective antiarthritic amount of the compound of claim 6.
Claim 21
Dependent Claim
19 words
A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective antiarthritic amount of the compound of claim 7.
Claim 22
Dependent Claim
19 words
A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective antiarthritic amount of the compound of claim 8.
Claim 23
Dependent Claim
19 words
A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective antiarthritic amount of the compound of claim 9.
Claim 24
Dependent Claim
19 words
A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective antiarthritic amount of the compound of claim 10.
Claim 25
Dependent Claim
19 words
A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective antiarthritic amount of the compound of claim 11.
Claim 26
Dependent Claim
19 words
A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective antiarthritic amount of the compound of claim 12.
Claim 27
Dependent Claim
19 words
A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective antiarthritic amount of the compound of claim 13.
Claim 28
Dependent Claim
28 words
A method of treating arthritis in a mammal in need of treatment which comprises administering to the mammal an effective anti-arthritic amount of the compound of claim 1.
Claim 29
Dependent Claim
28 words
A method of treating arthritis in a mammal in need of treatment which comprises administering to the mammal an effective anti-arthritic amount of the compound of claim 2.
Claim 30
Dependent Claim
28 words
A method of treating arthritis in a mammal in need of treatment which comprises administering to the mammal an effective anti-arthritic amount of the compound of claim 3.
Claim 31
Dependent Claim
28 words
A method of treating arthritis in a mammal in need of treatment which comprises administering to the mammal an effective anti-arthritic amount of the compound of claim 4.
Claim 32
Dependent Claim
28 words
A method of treating arthritis in a mammal in need of treatment which comprises administering to the mammal an effective anti-arthritic amount of the compound of claim 5.
Claim 33
Dependent Claim
28 words
A method of treating arthritis in a mammal in need of treatment which comprises administering to the mammal an effective anti-arthritic amount of the compound of claim 6.
Claim 34
Dependent Claim
28 words
A method of treating arthritis in a mammal which comprises administering to the mammal in need of treatment an effective anti-arthritic amount of the compound of claim 7.
Claim 35
Dependent Claim
28 words
A method of treating arthritis in a mammal in need of treatment which comprises administering to the mammal an effective anti-arthritic amount of the compound of claim 8.
Claim 36
Dependent Claim
28 words
A method of treating arthritis in a mammal in need of treatment which comprises administering to the mammal an effective antiarthritic amount of the compound of claim 9.
Claim 37
Dependent Claim
28 words
A method of treating arthritis in a mammal in need of treatment which comprises administering to the mammal an effective antiarthritic amount of the compound of claim 10.
Claim 38
Dependent Claim
28 words
A method of treating arthritis in a mammal in need of treatment which comprises administering to the mammal an effective anti-arthritic amount of the compound of claim 11.
Claim 39
Dependent Claim
28 words
A method of treating arthritis in a mammal in need of treatment which comprises administering to the mammal an effective anti-arthritic amount of the compound of claim 12.
Claim 40
Dependent Claim
28 words
A method of treating arthritis in a mammal in need of treatment which comprises administering to the mammal an effective anti-arthritic amount of the compound of claim 13.
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) | 1982-06-25 | 1982-12-25 | 1983-06-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-06-25 | 1986-12-25 | 1987-06-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-06-25 | 1990-12-25 | 1991-06-26 | $7700.00 | Window Closed / Lapsed |