US4526967A
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US
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Benzoquinolizines and use as α2 -adrenoceptor antagonistics
Assignee: John Wyeth and Brother Ltd
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Filing: 1984-03-19
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Granted: 1985-07-02
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Expires: 2004-03-19
Abstract
Abstract The invention concerns benzoquinolizines of general formula ##STR1## and their pharmaceutically acceptable acid addition salts. In formula (I), R represents hydrogen or lower alkyl, R 1 and R 2 which may be the same or different each represent hydrogen, lower alkyl, lower alkoxy or halogen, R 3 and R 4 which may be the same or different each represents lower alkyl, halo(lower)alkyl or aryl and A represents a lower alkylene group having 1 to 3 carbon atoms in the chain between the two N atoms. The compounds possess α 2 -adrenoceptor antagonistic activity in warm blooded animals.
Inventors
- 👤 Terence J. Ward
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 19:28
CPC Classifications
C; C07; C07D; C07D455/00; C07D455/03; C07D455/04; C07D455/06
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
90 words
A compound selected from the group consisting of a benzoquinolizine of the formula ##STR12## and a pharmaceutically acceptable acid addition salt thereof, wherein R represents hydrogen or lower alkyl, R 1 and R 2 which may be the same or different each represent hydrogen, lower alkyl, lower alkoxy or halogen, R 3 and R 4 which may be the same or different each represents lower alkyl, halo(lower)alkyl or aryl and A represents a lower alkylene group having 1 to 3 carbon atoms in the chain between the two N atoms.
Claim 2
Dependent Claim
90 words
A compound selected from the group consisting of a benzoquinolizine of the formula ##STR12## and a pharmaceutically acceptable acid addition salt thereof, wherein R represents hydrogen or lower alkyl, R 1 and R 2 which may be the same or different each represent hydrogen, lower alkyl, lower alkoxy or halogen, R 3 and R 4 which may be the same or different each represents lower alkyl, halo(lower)alkyl or aryl and A represents a lower alkylene group having 1 to 3 carbon atoms in the chain between the two N atoms.
Claim 3
Dependent Claim
11 words
A compound as claimed in claim 1 wherein A is ethylene.
Claim 4
Dependent Claim
15 words
A compound according to claim 1 which is N-[(2β,11bα)-1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizin-2-yl]-N-(2-methanesulphonamidoethyl)methanesulphonamide or a pharmaceutically acceptable salt thereof.
Claim 5
Dependent Claim
15 words
A compound according to claim 1 which is N-((2β,11bα)-1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizine-2-yl)-N-(2-methanesulphonamidoethyl)-n-propanesulphonamide or a pharmaceutically acceptable salt thereof.
Claim 6
Dependent Claim
15 words
A compound according to claim 1 which is N-((2β,11bα)-1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizin-2-yl)-N-(2-methanesulphonamidoethyl)benzenesulphonamide or a pharmaceutically acceptable salt thereof.
Claim 7
Dependent Claim
24 words
A compound according to claim 1 which is N-[(2β,11bα)-1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizin-2-yl]-N-(2-N'-methylmethanesulphonamido)ethylmethanesulphonamide, N-((2β, 11bα)-1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizine-2-yl)-N-(2-(1-propanesulphonamido)ethyl)methanesulphonamide, N-(2-[N'-((2β,11bα)-1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizin-2-yl)methanesulphonamido]ethyl)benzenesulphonamide, N-((2β,11bα)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizin-2-yl)-N-(2-methanesulphonamidoethyl)methanesulphonamide, N-[(2β,11bα)-1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizin-2-yl]-N-(2-chloromethanesulphonamidoethyl)chloromethanesulphonamide or N-((2β,11bα)-1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizin-2-yl)(3-methanesulphonamido-n-propyl)methanesulphonamide or a pharmaceutically acceptable acid addition salt thereof.
Claim 8
Dependent Claim
116 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 ##STR13## and a pharmaceutically acceptable acid addition salt thereof, wherein R represents hydrogen or lower alkyl, R 1 and R 2 which may be the same or different each represent hydrogen, lower alkyl, lower alkoxy or halogen, R 3 and R 4 which may be the same or different each represents lower alkyl, halo(lower)alkyl or aryl and A represents a lower alkylene group having 1 to 3 carbon atoms in the chain between the two N atoms, in association with a pharmaceutically acceptable carrier.
Claim 9
Dependent Claim
116 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 ##STR13## and a pharmaceutically acceptable acid addition salt thereof, wherein R represents hydrogen or lower alkyl, R 1 and R 2 which may be the same or different each represent hydrogen, lower alkyl, lower alkoxy or halogen, R 3 and R 4 which may be the same or different each represents lower alkyl, halo(lower)alkyl or aryl and A represents a lower alkylene group having 1 to 3 carbon atoms in the chain between the two N atoms, in association with a pharmaceutically acceptable carrier.
Claim 10
Independent Claim
111 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 ##STR14## and a pharmaceutically acceptable acid addition salt thereof, wherein R represents hydrogen or lower alkyl, R 1 and R 2 which may be the same or different each represent hydrogen, lower alkyl, lower alkoxy or halogen, R 3 and R 4 which may be the same or different each represents lower alkyl, halo(lower)alkyl or aryl and A represents a lower alkylene group having 1 to 3 carbon atoms in the chain between the two N atoms.
Claim 11
Independent Claim
111 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 ##STR14## and a pharmaceutically acceptable acid addition salt thereof, wherein R represents hydrogen or lower alkyl, R 1 and R 2 which may be the same or different each represent hydrogen, lower alkyl, lower alkoxy or halogen, R 3 and R 4 which may be the same or different each represents lower alkyl, halo(lower)alkyl or aryl and A represents a lower alkylene group having 1 to 3 carbon atoms in the chain between the two N atoms.
Claim 12
Dependent Claim
89 words
A compound of the formula ##STR15## wherein R 1 , R 2 and A are as defined in claim 1 and Z 1 and Z 2 are both hydrogen and R is hydrogen or lower alkyl or Z 1 is hydrogen, Z 2 is SO 2 R 4 (where R 4 is as defined in claim 1) and R is hydrogen or lower alkyl or Z 1 is SO 2 R 3 (where R 3 is as defined in claim 1), Z 2 is hydrogen and R is hydrogen.
Claim 13
Dependent Claim
18 words
A compound according to claim 1 which is N-[(2β, 11bα)-1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizin-2yl]-N-(2-ethanesulphonamidoethyl)-ethanesulphonamide or N-[(2β,11bα)-1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizin-2-yl]-N-(2-methanesulphonamidoethyl)-ethanesulphonamide or a pharmaceutically acceptable salt thereof.
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) | 1988-07-01 | 1988-12-31 | 1989-07-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-07-01 | 1992-12-31 | 1993-07-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-07-01 | 1996-12-31 | 1997-07-02 | $7700.00 | Window Closed / Lapsed |