US3979381A
Expired / Lapsed
US
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Thiopyrano[4,3-c] pyrazoles
Assignee: ER Squibb and Sons LLC
•
Filing: 1975-08-11
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Granted: 1976-09-07
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Expires: 1995-08-11
Abstract
Abstract Anti-inflammatory activity is exhibited by compounds having the formula ##SPC1## The salts thereof, and the 5-oxide and 5,5-dioxide thereof, wherein R 1 is hydrogen, alkyl, aryl, arylalkyl, or acyl; and R 2 and R 3 are the same or different and are hydrogen, alkyl, hydroxy, alkoxy, alkylthio, alkylsulfinyl, trifluoromethyl, halogen, acyl, cyano, nitro, or dialkylamino.
Inventors
- 👤 George C. Rovnyak
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 11:28
CPC Classifications
C; C07; C07D; C07D495/00; C07D495/02; C07D495/04; A; A61; A61P; A61P29/00; C07D335/00; C07D335/02
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
95 words
A compound having the formula ##SPC5## or a pharmaceutically acceptable acid addition salt thereof, or a 5-oxide or 5,5-dioxide thereof, wherein R 1 is hydrogen, alkyl, aryl, arylalkyl, or ##EQU1## wherein X is alkyl or aryl; and R 2 and R 3 are the same or different and are hydrogen, alkyl, hydroxy, alkoxy, alkylthio, alkylsulfinyl, trifluoromethyl, halogen, ##EQU2## cyano, nitro or dialkylamino; wherein the terms alkyl and alkoxy refer to groups having 1 to 8 carbon atoms and the term aryl refers to phenyl or phenyl monosubstituted with an alkyl, alkoxy, halogen, or trifluoromethyl group.
Claim 2
Dependent Claim
95 words
A compound having the formula ##SPC5## or a pharmaceutically acceptable acid addition salt thereof, or a 5-oxide or 5,5-dioxide thereof, wherein R 1 is hydrogen, alkyl, aryl, arylalkyl, or ##EQU1## wherein X is alkyl or aryl; and R 2 and R 3 are the same or different and are hydrogen, alkyl, hydroxy, alkoxy, alkylthio, alkylsulfinyl, trifluoromethyl, halogen, ##EQU2## cyano, nitro or dialkylamino; wherein the terms alkyl and alkoxy refer to groups having 1 to 8 carbon atoms and the term aryl refers to phenyl or phenyl monosubstituted with an alkyl, alkoxy, halogen, or trifluoromethyl group.
Claim 3
Dependent Claim
12 words
A compound in accordance with claim 1 wherein R 1 is hydrogen.
Claim 4
Dependent Claim
12 words
A compound in accordance with claim 1 wherein R 1 is alkyl.
Claim 5
Dependent Claim
12 words
A compound in accordance with claim 1 wherein R 1 is aryl.
Claim 6
Dependent Claim
12 words
A compound in accordance with claim 1 wherein R 1 is arylalkyl.
Claim 7
Dependent Claim
12 words
A compound in accordance with claim 1 wherein R 1 is ##STR3##
Claim 8
Dependent Claim
12 words
A compound in accordance with claim 1 wherein R 1 is ##STR4##
Claim 9
Dependent Claim
26 words
A compound in accordance with claim 1 wherein R 2 and R 3 are the same or different and are hydrogen, alkyl, alkoxy, trifluoromethyl, or halogen.
Claim 10
Dependent Claim
12 words
A compound in accordance with claim 1 wherein R 2 is hydrogen.
Claim 11
Dependent Claim
12 words
A compound in accordance with claim 8 wherein R 2 is hydrogen.
Claim 12
Dependent Claim
11 words
The compound in accordance with claim 1 having the name 2,3,3a,4,6,7-hexahydro-3-phenyl-7-(phenylmethylene)-2-propylthiopyrano[4,3-c]pyrazole.
Claim 13
Dependent Claim
11 words
The compound in accordance with claim 1 having the name 2,3,3a,4,6,7-hexahydro-3-(4-methoxyphenyl)-7-[(4-methoxyphenyl)methylene]-2-propylthiopyrano[4,3-c]pyrazole.
Claim 14
Dependent Claim
11 words
The compound in accordance with claim 1 having the name 3-(4-chlorophenyl)-7-[(4-chlorophenyl)methylene]-2,3,3a,4,6,7-hexahydro-2-propylthiopyrano[4,3-c]pyrazole.
Claim 15
Dependent Claim
11 words
The compound in accordance with claim 1 having the name 2,3,3a,4,6,7-hexahydro-3-phenyl-7-(phenylmethylene)-2-propylthiopyrano[4,3-c]pyrazole-5,5-dioxide.
Claim 16
Dependent Claim
11 words
The compound in accordance with claim 1 having the name 2,3,3a,4,6,7-hexahydro-3-phenyl-7-(phenylmethylene)-2-propylthiopyrano[4,3-c]pyrazole-5-oxide.
Claim 17
Dependent Claim
12 words
The compound in accordance with claim 1 having the name 2,3,3a,4,6,7-hexahydro-3-(4-methoxyphenyl)-7-[( 4-methoxyphenyl)methylene]-2-propylthiopyran[4,3-c]pyrazole-5-oxide.
Claim 18
Dependent Claim
11 words
The compound in accordance with claim 1 having the name 3-(4-chlorophenyl)-7-[-(4-chlorophenyl)methylene]-2,3,3a,4,6,7-hexahydro-2-propylthiopyrano[4,3-c]pyrazole-5,5-dioxide.
Claim 19
Dependent Claim
11 words
The compound in accordance with claim 1 having the name 2,3,3a,4,6,7-hexahydro-3-(4-methoxyphenyl)-7-[(4-methoxyphenyl)methylene]-2-propylthiopyrano[4,3-c]pyrazole-5,5-dioxide.
Claim 20
Dependent Claim
11 words
The compound in accordance with claim 1 having the name 3-(3,4-dichlorophenyl)-7-[(3,4-dichlorophenyl)methylene]2,3,3a,4,6,7-hexahydro-2-propylthiopyrano[4,3-c]pyrazole.
Claim 21
Dependent Claim
11 words
The compound in accordance with claim 1 having the name 2,3,3a,4,6,7-hexahydro-2-propyl-3-[3-(trifluoromethyl)phenyl]-7-[[3-(trifluoromethyl)phenyl]methylene]thiopyrano[4,3-c]pyrazole-5,5-dioxide.
Claim 22
Dependent Claim
11 words
The compound in accordance with claim 1 having the name 2,3,3a,4,6,7-hexahydro-2-propyl-3-[3-(trifluoromethyl)phenyl]-7-[[3-(trifluoromethyl)phenyl]methylene]thiopyrano[4,3-c]pyrazole.
Claim 23
Dependent Claim
11 words
The compound in accordance with claim 1 having the name 2,3,3a,4,6,7-hexahydro-3-(2-methylphenyl)-7-[(2-methylphenyl)methylene]-2-propylthiopyrano[4,3-c]pyrazole.
Claim 24
Dependent Claim
11 words
The compound in accordance with claim 1 having the name 2,3,3a,4,6,7-hexahydro-3-phenyl-7-(phenylmethylene)thiopyrano[4,3-c]pyrazole-5,5-dioxide.
Claim 25
Dependent Claim
11 words
The compound in accordance with claim 1 having the name 2-acetyl-2,3,3a,4,6,7-hexahydro-3-phenyl-7-(phenylmethylene)thiopyrano[4,3-c]pyrazole-5,5-dioxide.
Claim 26
Dependent Claim
11 words
The compound in accordance with claim 1 having the name 3-(4-chlorophenyl)-7-[(4-chlorophenyl)methylene]-2,3,3a,4,6,7-hexahydro-2-phenylthiopyrano[4,3-c]pyrazole-5,5-dioxide.
Claim 27
Dependent Claim
12 words
The compound in accordance with claim 1 having the name 2,3,3a,4,6,7-hexahydro-3-[3-(trifluoromethyl)phenyl]-7- [[3-(trifluoromethyl)phenyl]methylene]thiopyrano[4,3-c]pyrazole-5,5-dioxide.
Claim 28
Dependent Claim
11 words
The compound in accordance with claim 1 having the name 2-acetyl-2,3,3a,4,6,7-hexahydro-3-[3-(trifluoromethyl)phenyl]-7-[[3-(trifluoromethyl)phenyl]methylene]thiopyrano[4,3-c]pyrazole-5,5-dioxide.
Claim 29
Dependent Claim
11 words
The compound in accordance with claim 1 having the name 2,3,3a,4,6,7-hexahydro-3-phenyl-7-(phenylmethylene)thiopyrano[4,3-c]pyrazole.
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) | 1979-09-07 | 1980-03-08 | 1980-09-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-09-07 | 1984-03-08 | 1984-09-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-09-07 | 1988-03-08 | 1988-09-07 | $7700.00 | Window Closed / Lapsed |