US4265890A
Expired / Lapsed
US
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6-Phenyl thio- and 6-cyclohexyl thio-2,3,4,5-tetrahydro-1H-3-benzazepines
Assignee: SmithKline Beecham Corp
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Filing: 1979-05-17
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Granted: 1981-05-05
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Expires: 1999-05-17
Abstract
Abstract Mercapto substituted-2,3,4,5-tetrahydro-1H-3-benzazepines having dopamine receptor blocking activity are prepared from o-quinones or via standard preparative procedures.
Inventors
- 👤 Kenneth G. Holden
- 👤 Carl Kaiser
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 01:50
CPC Classifications
C; C07; C07D; C07D223/00; C07D223/14; C07D223/16; C07C; C07C41/00; C07C41/01; C07C41/16; C07C41/18; C07C41/26; C07C41/30; C07F; C07F5/00; C07F5/02; C07F5/022
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
102 words
A compound represented by the formula: ##STR4## wherein: R is methyl, allyl, dimethylallyl, phenethyl, cyclopropylmethyl or β-hydroxyethyl; R 1 is phenyl, m- or p-substituted phenyl with the substituent being trifluoromethyl, chloro, methoxy, methyl, fluoro, nitro or hydroxy or cyclohexyl; R 2 is hydrogen, methoxy, alkanoyloxy with the alkanoyl moiety having from 2 to 6 carbon atoms, or hydroxy, each R 2 being the same or different except that when one of R 2 is alkanoyloxy the other is hydrogen, methoxy or alkanoyloxy; and R 3 is hydrogen, chloro, bromo, trifluoromethyl, fluoro or methyl, or a nontoxic pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
102 words
A compound represented by the formula: ##STR4## wherein: R is methyl, allyl, dimethylallyl, phenethyl, cyclopropylmethyl or β-hydroxyethyl; R 1 is phenyl, m- or p-substituted phenyl with the substituent being trifluoromethyl, chloro, methoxy, methyl, fluoro, nitro or hydroxy or cyclohexyl; R 2 is hydrogen, methoxy, alkanoyloxy with the alkanoyl moiety having from 2 to 6 carbon atoms, or hydroxy, each R 2 being the same or different except that when one of R 2 is alkanoyloxy the other is hydrogen, methoxy or alkanoyloxy; and R 3 is hydrogen, chloro, bromo, trifluoromethyl, fluoro or methyl, or a nontoxic pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
48 words
A compound according to claim 1 in which R is methyl, R 1 is phenyl, p-trifluoromethylphenyl, p-chlorophenyl, p-tolyl, p-fluorophenyl or cyclohexyl both R 2 are hydrogen, acetoxy or hydroxy, or one R 2 is hydroxy and the other is methoxy, and R 3 is hydrogen, chloro or bromo.
Claim 4
Dependent Claim
24 words
A compound according to claim 2 in which both R 2 are hydroxy, or one R 2 is hydroxy and the other is methoxy.
Claim 5
Dependent Claim
13 words
A compound according to claim 3 in which both R 2 are hydroxy.
Claim 6
Dependent Claim
10 words
A compound according to claim 3 being the compound 8-hydroxy-7-methoxy-3-methyl-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine.
Claim 7
Dependent Claim
10 words
A compound according to claim 4 being the compound 7,8-dihydroxy-3-methyl-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine.
Claim 8
Dependent Claim
10 words
A compound according to claim 4 being the compound 9-chloro-7,8-dihydroxy-3-methyl-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine.
Claim 9
Dependent Claim
10 words
A compound according to claim 4 being the compound 6-(p-fluorophenylthio)-7,8-dihydroxy-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine.
Claim 10
Dependent Claim
10 words
A compound according to claim 4 being the compound 9-bromo-7,8-dihydroxy-3-methyl-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine.
Claim 11
Dependent Claim
13 words
A compound according to claim 2 in which both R 2 are hydrogen.
Claim 12
Dependent Claim
10 words
A compound according to claim 10 being the compound 3-methyl-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine.
Claim 13
Dependent Claim
48 words
A pharmaceutical composition having dopamine receptor blocking activity in dosage unit form comprising a pharmaceutical carrier and a nontoxic amount sufficient to produce said activity of a compound of claims 1, 6, 7, 8, 9, 11 or 5, or a pharmaceutically acceptable acid addition salt of said compound.
Claim 14
Independent Claim
54 words
A method of producing dopamine receptor blocking activity which comprises administering internally to an animal or human subject in need of such activity a compound of claims 1, 6, 7, 8, 9, 11 or 5, or a pharmaceutically acceptable acid addition salt of said compound, in a nontoxic amount sufficient to produce said activity.
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) | 1984-05-04 | 1984-11-03 | 1985-05-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-05-04 | 1988-11-03 | 1989-05-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-05-04 | 1992-11-03 | 1993-05-05 | $7700.00 | Window Closed / Lapsed |