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US4481200A
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α2 -Adrenoceptor antagonistic benzoquinolizines
Assignee: John Wyeth and Brother Ltd
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Filing: 1983-03-03
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Granted: 1984-11-06
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Expires: 2003-03-03
Abstract
Abstract The invention concerns benzoquinolizines of formula ##STR1## and their pharmaceutically acceptable acid addition salts. In the formula R 1 and R 2 which may be the same or different each represent hydrogen, lower alkyl, lower alkoxy or halogen, R 3 represents methyl or ethyl, 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, R 4 and R 5 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. The compounds possess α 2 -adrenoceptor antagonistic activity and can be incorporated into pharmaceutical compositions.
Inventors
- 👤 Terence J. Ward
- 👤 John F. White
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 17:37
CPC Classifications
C; C07; C07D; C07D455/00; C07D455/03; C07D455/04; C07D455/06
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
142 words
A compound selected from the group consisting of a benzoquinolizine of the formula ##STR13## and a pharmaceutically acceptable acid addition salt thereof, wherein R 1 and R 2 each represent hydrogen, lower alkyl, lower alkoxy or halogen, R 3 represents methyl or ethyl, 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, R 4 and R 5 each independently represent hydrogen, lower alkyl, phenyl, phenyl loweralkyl, substituted phenyl or substituted phenyl loweralkyl wherein the phenyl substituents are selected from one or more of halogen, lower alkyl, lower alkoxy, lower alkylenedioxy, amino, mono- or di-lower alkylamino or trifluoromethyl, or R 4 and R 5 together with the nitrogen atom to which they are attached form a pyrrolidino, piperidino or morpholino ring.
Claim 2
Dependent Claim
142 words
A compound selected from the group consisting of a benzoquinolizine of the formula ##STR13## and a pharmaceutically acceptable acid addition salt thereof, wherein R 1 and R 2 each represent hydrogen, lower alkyl, lower alkoxy or halogen, R 3 represents methyl or ethyl, 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, R 4 and R 5 each independently represent hydrogen, lower alkyl, phenyl, phenyl loweralkyl, substituted phenyl or substituted phenyl loweralkyl wherein the phenyl substituents are selected from one or more of halogen, lower alkyl, lower alkoxy, lower alkylenedioxy, amino, mono- or di-lower alkylamino or trifluoromethyl, or R 4 and R 5 together with the nitrogen atom to which they are attached form a pyrrolidino, piperidino or morpholino ring.
Claim 3
Dependent Claim
17 words
A compound according to claim 1 which is N-methyl-N-(1,3,4,6,7,11bα-hexahydro-2H-benzo[a]quinolizin-2β-yl)-N'-methylsulphamide or a pharmaceutically acceptable acid addition salt thereof.
Claim 4
Dependent Claim
17 words
A compound according to claim 1 which is N,N,N'-trimethyl-N'-[1,3,4,6,7,11bα-hexahydro-2H-benzo[a]quinolizin-2β-yl]sulphamide or a pharmaceutically acceptable acid addition salt thereof.
Claim 5
Dependent Claim
17 words
A compound according to claim 1 which is N-methyl-N-(1,3,4,6,7,11bα-hexahydro-2H-benzo[a]quinolizin-2β-yl)-2-dimethylaminoethanesulphonamide or a pharmaceutically acceptable acid addition salt thereof.
Claim 6
Dependent Claim
17 words
A compound according to claim 1 which is N-(i-propyl)-N'-(1,3,4,6,7,11bα-hexahydro-2H-benzo[a]quinolizin-2.beta.-yl)-N'-methylsulphamide or a pharmaceutically acceptable acid addition salt thereof.
Claim 7
Dependent Claim
17 words
A compound according to claim 1 which is N-methyl-N-sulphamido-1,3,4,6,7,11bα-hexahydro-2H-benzo[a]quinolizin-2β-amine or a pharmaceutically acceptable acid addition salt thereof.
Claim 8
Dependent Claim
17 words
A compound according to claim 1 which is N-methyl-N-(1,3,4,6,7,11bα-hexahydro-2H-benzo[a]quinolizin-2β-yl)-2-aminoethanesulphonamide or a pharmaceutically acceptable acid addition salt thereof.
Claim 9
Dependent Claim
161 words
A pharmaceutical composition having α 2 -adrenoceptor antagonistic activity comprising an amount effective to antagonise α 2 -adrenoceptors of a compound selected from the group consisting of a benzoquinolizine of the formula ##STR14## and a pharmaceutically acceptable acid addition salt thereof, wehrein R 1 and R 2 each represent hydrogen, lower alkyl, lower alkoxy or halogen, R 3 represents methyl or ethyl, 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, R 4 and R 5 each independently represent hydrogen, lower alkyl, phenyl, phenyl loweralkyl, substituted phenyl or substituted phenyl loweralkyl wherein the phenyl substituents are selected from one or more of halogen, lower alkyl, lower alkoxy, lower alkylenedioxy, amino, mono- or di-lower alkylamino or trifluoromethyl, or R 4 and R 5 together with the nitrogen atom to which they are attached form a pyrrolidino, piperidino or morpholino ring.
Claim 10
Dependent Claim
161 words
A pharmaceutical composition having α 2 -adrenoceptor antagonistic activity comprising an amount effective to antagonise α 2 -adrenoceptors of a compound selected from the group consisting of a benzoquinolizine of the formula ##STR14## and a pharmaceutically acceptable acid addition salt thereof, wehrein R 1 and R 2 each represent hydrogen, lower alkyl, lower alkoxy or halogen, R 3 represents methyl or ethyl, 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, R 4 and R 5 each independently represent hydrogen, lower alkyl, phenyl, phenyl loweralkyl, substituted phenyl or substituted phenyl loweralkyl wherein the phenyl substituents are selected from one or more of halogen, lower alkyl, lower alkoxy, lower alkylenedioxy, amino, mono- or di-lower alkylamino or trifluoromethyl, or R 4 and R 5 together with the nitrogen atom to which they are attached form a pyrrolidino, piperidino or morpholino ring.
Claim 11
Independent Claim
163 words
A method of antagonising α 2 -adrenoceptors in warm blooded animals which comprises administering to the animal an effective amount of a compound selected from the group consisting of a benzoquinolizine of the formula ##STR15## and a pharmaceutically acceptable acid addition salt thereof, wherein R 1 and R 2 each represent hydrogen, lower alkyl, lower alkoxy or halogen, R 3 represents methyl or ethyl, 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, R 4 and R 5 each independently represent hydrogen, lower alkyl, phenyl, phenyl loweralkyl, substituted phenyl or substituted phenyl loweralkyl wherein the phenyl substituents are selected from one or more of halogen, lower alkyl, lower alkoxy, lower alkylenedioxy, amino, mono- or di-lower alkylamino or trifluoromethyl, or R 4 and R 5 together with the nitrogen atom to which they are attached form a pyrrolidino, piperidino or morpholino ring.
Claim 12
Independent Claim
163 words
A method of antagonising α 2 -adrenoceptors in warm blooded animals which comprises administering to the animal an effective amount of a compound selected from the group consisting of a benzoquinolizine of the formula ##STR15## and a pharmaceutically acceptable acid addition salt thereof, wherein R 1 and R 2 each represent hydrogen, lower alkyl, lower alkoxy or halogen, R 3 represents methyl or ethyl, 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, R 4 and R 5 each independently represent hydrogen, lower alkyl, phenyl, phenyl loweralkyl, substituted phenyl or substituted phenyl loweralkyl wherein the phenyl substituents are selected from one or more of halogen, lower alkyl, lower alkoxy, lower alkylenedioxy, amino, mono- or di-lower alkylamino or trifluoromethyl, or R 4 and R 5 together with the nitrogen atom to which they are attached form a pyrrolidino, piperidino or morpholino ring.
References Cited (Backward Citations)
US4183937A
Cited
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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) | 1987-11-06 | 1988-05-07 | 1988-11-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-11-06 | 1992-05-07 | 1992-11-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-11-06 | 1996-05-07 | 1996-11-06 | $7700.00 | Window Closed / Lapsed |