US4090020A
Expired / Lapsed
US
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Thienothiazine derivatives
Assignee: Hoffmann La Roche Inc
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Filing: 1977-02-09
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Granted: 1978-05-16
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Expires: 1997-02-09
Abstract
Abstract Thienothiazine derivatives of the formula <IMAGE> I wherein R1 is lower alkyl; R2 is an unsubstituted aromatic heterocyclic radical which contains from 1 to 4 hetero atoms or one which is substituted by one or two lower alkyl groups, or is an unsubstituted phenyl radical or one substituted by halogen, hydroxy, lower alkyl, nitro, trifluoromethyl or lower alkoxy; and R3 and R4, independently, are hydrogen or lower alkyl, PREPARED INTER ALIA, FROM NOVEL INTERMEDIATES, ARE DESCRIBED. The end products are useful as anti-inflammatory, analgesic and anti-rheumatic agents.
Inventors
- 👤 Dieter Binder
- 👤 Otto Hromatka
- 👤 Rudolf Pfister
- 👤 Paul Zeller
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 12:53
CPC Classifications
C; C07; C07D; C07D513/00; C07D513/02; C07D513/04; A; A61; A61P; A61P25/00; A61P25/04; A61P29/00; A61P7/00; A61P7/02; C07D333/00; C07D333/02; C07D333/04; C07D333/26; C07D333/30; C07D333/34; C07D333/38
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
87 words
A compound of the formula ##STR10## wherein R 1 is lower alkyl, R 2 is an unsubstituted aromatic heterocyclic radical selected from the group consisting of 2-thiazolyl, 4-methyl-2-thiazolyl, 4,5-dimethyl-2-thiazolyl, 5-methyl-1,3,4-thiadiazolyl, 2-pyrazinyl, 2-pyrimidinyl, 1,2,4-triazin-2-yl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 3-methyl-2-pyridyl, 4-methyl-2-pyridyl, 5-methyl-2-pyridyl, 6-methyl-2-pyridyl, 4,6-dimethyl-2-pyridyl, 5-isoxazolyl, 5-methyl-3-isoxazolyl, 3,4-dimethyl-5-isoxazolyl, 2,6-dimethyl-4-pyrimidinyl or 1,2,3,4-tetrazol-5-yl; a phenyl radical; or a phenyl radical substituted by halogen, hydroxy, lower alkyl, nitro, trifluoromethyl or lower alkoxy, and R 3 and R 4 , independently, are hydrogen or lower alkyl, or its tautomer or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
87 words
A compound of the formula ##STR10## wherein R 1 is lower alkyl, R 2 is an unsubstituted aromatic heterocyclic radical selected from the group consisting of 2-thiazolyl, 4-methyl-2-thiazolyl, 4,5-dimethyl-2-thiazolyl, 5-methyl-1,3,4-thiadiazolyl, 2-pyrazinyl, 2-pyrimidinyl, 1,2,4-triazin-2-yl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 3-methyl-2-pyridyl, 4-methyl-2-pyridyl, 5-methyl-2-pyridyl, 6-methyl-2-pyridyl, 4,6-dimethyl-2-pyridyl, 5-isoxazolyl, 5-methyl-3-isoxazolyl, 3,4-dimethyl-5-isoxazolyl, 2,6-dimethyl-4-pyrimidinyl or 1,2,3,4-tetrazol-5-yl; a phenyl radical; or a phenyl radical substituted by halogen, hydroxy, lower alkyl, nitro, trifluoromethyl or lower alkoxy, and R 3 and R 4 , independently, are hydrogen or lower alkyl, or its tautomer or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
32 words
A compound in accordance with claim 1, wherein R 2 is 2-thiazolyl, 4-methyl-2-thiazolyl, 4,5-dimethyl-2-thiazolyl, 5-methyl-1,3,4-thiadiazolyl, 2-pyrazinyl, 2-pyrimidinyl, 1,2,4-triazin-2-yl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 3-methyl-2-pyridyl, 4-methyl-2-pyridyl, 5-methyl-2-pyridyl, 6-methyl-2-pyridyl, 4,6-dimethyl-2-pyridyl, 5-isoxazolyl, 5-methyl-3-isoxazolyl, 3,4-dimethyl-5-isoxazolyl, 2,6-dimethyl-4-pyrimidinyl or 1,2,3,4-tetrazol-5-yl.
Claim 4
Dependent Claim
17 words
A compound in accordance with claim 2, wherein each of R 3 and R 4 is hydrogen.
Claim 5
Dependent Claim
12 words
A compound in accordance with claim 3, wherein R 1 is methyl.
Claim 6
Dependent Claim
15 words
A compound in accordance with claim 4, wherein R 2 is 2-thiazolyl, 5-methyl-3-isoxazolyl or 2-pyridyl.
Claim 7
Dependent Claim
23 words
A compound in accordance with claim 3, wherein R 2 is 4-fluorophenyl, 3-trifluoromethylphenyl, 2,4-dichlorophenyl, 4-bromophenyl, 4-nitropheyl, 3-chlorophenyl, 2-tolyl, 2,5-dichlorophenyl, 4-nitro-2-tolyl, 4-iodophenyl or 4-n-butylphenyl.
Claim 8
Dependent Claim
9 words
A compound in accordance with claim 1, 3,4-dihydro-2-methyl-3-oxo-4-(2-pyridyl-carbamoyl)-2H-thieno[2,3-e]1,2-thiazine 1,1-dioxide.
Claim 9
Dependent Claim
10 words
A compound in accordance with claim 1, 3,4-dihydro-2-methyl-3-oxo-4-(2-thiazolyl-carbamoyl)-2H-thieno[2,3-e] 1,2-thiazine 1,1-dioxide.
Claim 10
Dependent Claim
10 words
A compound in accordance with claim 1, 3-hydroxy-2-methyl-N-pyrazinyl-2H-thieno[2,3-e] 1,2-thiazine-4-carboxamide 1,1-dioxide.
Claim 11
Dependent Claim
10 words
A compound in accordance with claim 1, 4'-bromo-3-hydroxy-2-methyl-2H-thieno[2,3-e] 1,2-thiazine-4-carboxanilide 1,1-dioxide.
Claim 12
Dependent Claim
10 words
A compound in accordance with claim 1, 4'-chloro-3-hydroxy-2-methyl-2H-thieno[2,3-e] 1,2-thiazine-4-carboxanilide 1,1-dioxide.
Claim 13
Dependent Claim
29 words
A compound of the formula ##STR11## wherein R is lower alkyl, R 1 is lower alkyl, and R 3 and R 4 , independently are hydrogen or lower alkyl.
Claim 14
Dependent Claim
29 words
A compound of the formula ##STR11## wherein R is lower alkyl, R 1 is lower alkyl, and R 3 and R 4 , independently are hydrogen or lower alkyl.
Claim 15
Dependent Claim
10 words
A compound in accordance with claim 12, 3,4-dihydro-4-methoxycarbonyl-2-methyl-3-oxo-2H-thieno[2,3-e] 1,2-thiazine 1,1-dioxide.
Claim 16
Dependent Claim
25 words
A compound of the formula ##STR12## wherein R 1 is lower alkyl, and R 3 and R 4 , independently, are hydrogen or lower alkyl.
Claim 17
Dependent Claim
25 words
A compound of the formula ##STR12## wherein R 1 is lower alkyl, and R 3 and R 4 , independently, are hydrogen or lower alkyl.
Claim 18
Dependent Claim
10 words
A compound in accordance with claim 14, 3,4-dihydro-2-methyl-3-oxo-2H-thieno[2,3-e] 1,2-thiazine 1,1-dioxide.
References Cited (Backward Citations)
US3591584A
Cited
US3712889A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-05-15 | 1981-11-14 | 1982-05-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-05-15 | 1985-11-14 | 1986-05-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-05-15 | 1989-11-14 | 1990-05-16 | $7700.00 | Window Closed / Lapsed |