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US4640924A
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Thienoquinolizines and their use as α2 -adrenoceptor antagonists
Assignee: John Wyeth and Brother Ltd
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Filing: 1985-08-12
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Granted: 1987-02-03
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Expires: 2005-08-12
Abstract
Abstract The invention concerns thienoquinolizines of general formula (I) ##STR1## and their pharmaceutically acceptable acid addition salts. In the formula R 1 is hydrogen or lower alkyl and R 2 is lower alkyl, halo(lower)alkyl, --A--NR 3 R 4 [where A represents a direct bond between the S and N atoms or a lower alkylene group having 1 to 3 carbon atoms in the chain between the S and N atoms and R 3 and R 4 each independently represent hydrogen, lower alkyl, aryl or aryl(lower)alkyl or together with the nitrogen atom to which they are attached represent a five or six membered heterocyclic ring], aryl or a heterocyclic radical or R 1 is --A 1 NR 5 .SO 2 R 6 [where A 1 is a lower alkylene group having 1 to 3 carbon atoms in the chain between the two N atoms, R 5 is hydrogen or lower alkyl and R 6 is lower alkyl, halo(lower)alkyl or aryl] and R 2 is lower alkyl, halo(lower)alkyl or aryl. The compounds possess α 2 -adrenoceptor antagonistic activity in warm blooded animals.
Inventors
- 👤 Alan C. White
- 👤 Robin G. Shepherd
- 👤 Barry J. Langham
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 17:39
CPC Classifications
C; C07; C07D; C07D495/00; C07D495/12; C07D495/14
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
136 words
A compound selected from the group consisting of a thienoquinolizine of the formula ##STR14## and a pharmaceutically acceptable acid addition salt thereof, where R 1 is --A 1 NR 5 .SO 2 R 6 (where A 1 is a lower alkylene group having 1 to 3 carbon atoms in the chain between the two N atoms, R 5 is hydrogen or lower alkyl and R 6 is lower alkyl, halo(lower)alkyl, phenyl or phenyl substituted by one or more substituents selected from the group consisting of halogen, lower alkoxy, lower alkyl, loweralkylenedioxy, nitro, amino, loweralkylcarbonylamino, lower alkylamino, diloweralkylamino or trifluoromethyl) and R 2 is lower alkyl, halo(lower)alkyl, phenyl or phenyl substituted by one or more substituents selected from the group consisting of halogen, lower alkoxy, lower alkyl, lower alkylenedioxy, nitro, amino, loweralkylcarbonylamino, lower alkylamino, diloweralkylamino or trifluoromethyl.
Claim 2
Dependent Claim
136 words
A compound selected from the group consisting of a thienoquinolizine of the formula ##STR14## and a pharmaceutically acceptable acid addition salt thereof, where R 1 is --A 1 NR 5 .SO 2 R 6 (where A 1 is a lower alkylene group having 1 to 3 carbon atoms in the chain between the two N atoms, R 5 is hydrogen or lower alkyl and R 6 is lower alkyl, halo(lower)alkyl, phenyl or phenyl substituted by one or more substituents selected from the group consisting of halogen, lower alkoxy, lower alkyl, loweralkylenedioxy, nitro, amino, loweralkylcarbonylamino, lower alkylamino, diloweralkylamino or trifluoromethyl) and R 2 is lower alkyl, halo(lower)alkyl, phenyl or phenyl substituted by one or more substituents selected from the group consisting of halogen, lower alkoxy, lower alkyl, lower alkylenedioxy, nitro, amino, loweralkylcarbonylamino, lower alkylamino, diloweralkylamino or trifluoromethyl.
Claim 3
Dependent Claim
12 words
A compound according to claim 1 wherein R 2 is lower alkyl.
Claim 4
Dependent Claim
19 words
A compound according to claim 1 which is N-(4,5,8,9a, 10,10aα-hexahydro-7H-thieno[2,3-a]quinolizin-9-yl)-N-(2-ethanesulphonamidoethyl)ethane sulphonamide or a pharmaceutically acceptacle acid addition salt thereof.
Claim 5
Dependent Claim
160 words
A composition having α 2 -adrenoceptor antagonistic activity comprising an amount sufficient to antagonise α 2 adrenoceptors of a compound selected from the group consisting of a thienoquinolizine of the formula ##STR15## and a pharmaceutically acceptable acid addition salt thereof, where R 1 is --A 1 NR 5 .SO 2 R 6 (where A 1 is a lower alkylene group having 1 to 3 carbon atoms in the chain between the two N atoms, R 5 is hydrogen or lower alkyl and R 6 is lower alkyl, halo(lower)alkyl, phenyl or phenyl substituted by one or more substituents selected from the group consisting of halogen, lower alkoxy, lower alkyl, loweralkylenedioxy, nitro amino, loweralkylcarbonylamino, lower alkylamino, diloweralkylamino or trifluoromethyl) and R 2 is lower alkyl, halo(lower)alkyl, phenyl or phenyl substituted by one or more substituents selected from the group consisting of halogen, lower alkoxy, lower alkyl, loweralkylenedioxy, nitro, amino, loweralkylcarbonylamino, lower alkylamino, diloweralkylamino or trifluoromethyl in association with a pharmaceutically acceptable carrier.
Claim 6
Dependent Claim
160 words
A composition having α 2 -adrenoceptor antagonistic activity comprising an amount sufficient to antagonise α 2 adrenoceptors of a compound selected from the group consisting of a thienoquinolizine of the formula ##STR15## and a pharmaceutically acceptable acid addition salt thereof, where R 1 is --A 1 NR 5 .SO 2 R 6 (where A 1 is a lower alkylene group having 1 to 3 carbon atoms in the chain between the two N atoms, R 5 is hydrogen or lower alkyl and R 6 is lower alkyl, halo(lower)alkyl, phenyl or phenyl substituted by one or more substituents selected from the group consisting of halogen, lower alkoxy, lower alkyl, loweralkylenedioxy, nitro amino, loweralkylcarbonylamino, lower alkylamino, diloweralkylamino or trifluoromethyl) and R 2 is lower alkyl, halo(lower)alkyl, phenyl or phenyl substituted by one or more substituents selected from the group consisting of halogen, lower alkoxy, lower alkyl, loweralkylenedioxy, nitro, amino, loweralkylcarbonylamino, lower alkylamino, diloweralkylamino or trifluoromethyl in association with a pharmaceutically acceptable carrier.
Claim 7
Independent Claim
161 words
A method of antagonising α 2 adrenoceptors in warm blooded animals which comprises administering to the animal an amount sufficient to antagonise α 2 adrenoceptors of a compound selected from the group consisting of a thienoquinolizine of the formula ##STR16## and a pharmaceutically acceptable acid addition salt thereof, where R 1 is --A 1 NR 5 .SO 2 R 6 (wherein A 1 is a lower alkylene group having 1 to 3 carbon atoms in the chain between the two N atoms, R 5 is hydrogen or lower alkyl and R 6 is lower alkyl, halo(lower)alkyl, phenyl or phenyl substituted by one or more substituents selected from the group consisting of halogen, lower alkoxy, lower alkyl, loweralkylenedioxy, nitro, amino, loweralkylcarbonylamino, lower alkylamino, diloweralkylamino or trifluoromethyl) and R 2 is lower alkyl, halo(lower)alkyl, phenyl or phenyl suhstituted by one or more substituents selected from the group consisting of halogen, lower alkoxy, lower alkyl, loweralkylenedioxy, nitro, amino, loweralkylcarbonylamino, lower alkylamino, diloweralkylamino or trifluoromethyl.
Claim 8
Independent Claim
161 words
A method of antagonising α 2 adrenoceptors in warm blooded animals which comprises administering to the animal an amount sufficient to antagonise α 2 adrenoceptors of a compound selected from the group consisting of a thienoquinolizine of the formula ##STR16## and a pharmaceutically acceptable acid addition salt thereof, where R 1 is --A 1 NR 5 .SO 2 R 6 (wherein A 1 is a lower alkylene group having 1 to 3 carbon atoms in the chain between the two N atoms, R 5 is hydrogen or lower alkyl and R 6 is lower alkyl, halo(lower)alkyl, phenyl or phenyl substituted by one or more substituents selected from the group consisting of halogen, lower alkoxy, lower alkyl, loweralkylenedioxy, nitro, amino, loweralkylcarbonylamino, lower alkylamino, diloweralkylamino or trifluoromethyl) and R 2 is lower alkyl, halo(lower)alkyl, phenyl or phenyl suhstituted by one or more substituents selected from the group consisting of halogen, lower alkoxy, lower alkyl, loweralkylenedioxy, nitro, amino, loweralkylcarbonylamino, lower alkylamino, diloweralkylamino or trifluoromethyl.
References Cited (Backward Citations)
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1990-02-02 | 1990-08-04 | 1991-02-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-02-02 | 1994-08-04 | 1995-02-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-02-02 | 1998-08-04 | 1999-02-03 | $7700.00 | Window Closed / Lapsed |