US4208523A
Expired / Lapsed
US
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11-Lower-alkyl-, 11-phenyl-lower-alkyl- and 11-cyclo-lower-alkyl-lower-alkyl-hexahydro-2,6-methano-3-benzazocines
Assignee: Sanofi SA
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Filing: 1978-11-30
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Granted: 1980-06-17
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Expires: 1998-11-30
Abstract
Abstract 3-R1-7-R2''-8-R2-9-R2'-10-R2'''-11(ax)-R3-6(eq)-R4-11(eq)-(CH2CH2CH2R5 )-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocines, generally useful as morphine-like analgesics and as narcotic antagonists, are prepared by reducing, under Wolff-Kishner reaction conditions, a corresponding 3-R1-7-R2''-8-R2-9-R2'-10-R2'''-11(ax)-R3-6(eq)-R4-11(eq)-(CH2CH2COR5) -1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine and, if desired, cleaving a lower-alkoxy, methoxymethoxy or benzyloxy group to an hydroxy group.
Inventors
- 👤 William F. Michne
- 👤 Thomas R. Lewis
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 01:50
CPC Classifications
C; C07; C07D; C07D221/00; C07D221/02; C07D221/22; C07D221/26; A; A61; A61P; A61P25/00; A61P25/04; A61P25/30
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
137 words
A member of the group consisting of (A) compounds having the formula ##STR3## where R 1 is lower-alkyl, lower-alkenyl, cyclo-lower-alkyl-lower-alkyl, hydrogen or benzyl; one of R 2 , R 2 ', R 2 " and R 2 "' is hydroxy, lower-alkoxy, methoxymethoxy, benzyloxy or lower-alkanoyloxy, the others being hydrogen; R 3 is hydrogen or lower-alkyl; R 4 is lower-alkyl, or R 3 and R 4 together represent lower-alkylene, (CH 2 ) n , where n is one of the integers 3 or 4; and R 5 is lower-alkyl containing from three to six carbon atoms, phenyl, phenyl-lower-alkyl, cyclo-lower-alkyl or cyclo-lower-alkyl-lower-alkyl, or such phenyl and phenyl-lower-alkyl groups substituted in the phenyl ring by a lower-alkyl group, and (B) acid-addition salts thereof with the proviso that R 3 and the group (CH 2 ) 3 R 5 are dissimilar.
Claim 2
Dependent Claim
137 words
A member of the group consisting of (A) compounds having the formula ##STR3## where R 1 is lower-alkyl, lower-alkenyl, cyclo-lower-alkyl-lower-alkyl, hydrogen or benzyl; one of R 2 , R 2 ', R 2 " and R 2 "' is hydroxy, lower-alkoxy, methoxymethoxy, benzyloxy or lower-alkanoyloxy, the others being hydrogen; R 3 is hydrogen or lower-alkyl; R 4 is lower-alkyl, or R 3 and R 4 together represent lower-alkylene, (CH 2 ) n , where n is one of the integers 3 or 4; and R 5 is lower-alkyl containing from three to six carbon atoms, phenyl, phenyl-lower-alkyl, cyclo-lower-alkyl or cyclo-lower-alkyl-lower-alkyl, or such phenyl and phenyl-lower-alkyl groups substituted in the phenyl ring by a lower-alkyl group, and (B) acid-addition salts thereof with the proviso that R 3 and the group (CH 2 ) 3 R 5 are dissimilar.
Claim 3
Dependent Claim
35 words
A compound according to claim 1 wherein R 1 is lower-alkyl, lower-alkenyl or cyclo-lower-alkyl -lower-alkyl; and one of R 2 , R 2 ', R 2 " and R 2 "' is hydroxy or lower-alkoxy.
Claim 4
Dependent Claim
41 words
A compound according to claim 2 where R 1 is lower-alkyl; R 2 is hydroxy or lower-alkoxy; R 2 ', R 2 " and R 2 "' are each hydrogen; R 3 is hydrogen or lower-alkyl; and R 4 is lower-alkyl.
Claim 5
Dependent Claim
21 words
A compound according to claim 3 where R 5 is phenyl or phenyl-substituted in the phenyl ring by a lower-alkyl group.
Claim 6
Dependent Claim
22 words
A compound according to claim 3 where R 5 is phenyl-lower-alkyl or phenyl-lower-alkyl substituted in the phenyl ring by a lower-alkyl group.
Claim 7
Dependent Claim
11 words
A compound according to claim 3 where R 5 is cyclo-lower-alkyl.
Claim 8
Dependent Claim
11 words
A compound according to claim 3 where R 5 is cyclo-lower-alkyl-lower-alkyl.
Claim 9
Dependent Claim
5 words
8-Hydroxy-3,6(eq)-dimethyl-1,2,3,4,5,6-hexahydro-11(eq)-octyl-2,6-methano-3-benzazocine according to claim 3.
Claim 10
Dependent Claim
5 words
8-Hydroxy-3,6(eq),11(ax)-trimethyl-1,2,3,4,5,6-hexahydro-11(eq)-octyl-2,6-methano-3-benzazocine according to claim 3.
Claim 11
Dependent Claim
5 words
8-Hydroxy-3,6(eq),11(ax)-trimethyl-1,2,3,4,5,6-hexahydro-11(eq)-nonyl-2,6-methano-3-benzazocine according to claim 3.
Claim 12
Dependent Claim
5 words
8-Hydroxy-3,6(eq)-dimethyl-1,2,3,4,5,6-hexahydro-11(eq)-heptyl-2,6-methano-3-benzazocine according to claim 3.
Claim 13
Dependent Claim
5 words
8-Hydroxy-3,6(eq)-dimethyl-1,2,3,4,5,6-hexahydro-11(eq)-(6-methylheptyl)-2,6-methano-3-benzazocine according to claim 3.
Claim 14
Dependent Claim
5 words
8-Hydroxy-3,6(eq),11(ax)-trimethyl-1,2,3,4,5,6-hexahydro-11(eq)-(6-methylheptyl)-2,6-methano-3-benzazocine according to claim 3.
Claim 15
Dependent Claim
5 words
8-Hydroxy-3,6(eq),11(ax)-trimethyl-1,2,3,4,5,6-hexahydro-11(eq)-heptyl-2,6-methano-3-benzazocine according to claim 3.
Claim 16
Dependent Claim
5 words
8-Hydroxy-3,6(eq),11(ax)-trimethyl-1,2,3,4,5,6-hexahydro-11(eq)-hexyl-2,6-methano-3-benzazocine according to claim 3.
Claim 17
Dependent Claim
5 words
8-Methoxy-3,6(eq),11(ax)-trimethyl-1,2,3,5,6-hexahydro-11(eq)-octyl-2,6-methano-3-benzazocine according to claim 3.
Claim 18
Dependent Claim
5 words
8-Hydroxy-3,6(eq),11(ax)-trimethyl-1,2,3,4,5,6hexahydro-11(eq)-(4-methylpentyl)-2,6-methano-3-benzazocine according to claim 3.
Claim 19
Dependent Claim
5 words
8-Hydroxy-3,6(eq),11(ax)-trimethyl-1,2,3,4,5,6-hexahydro-11(eq)-(3-phenylpropyl)-2,6-methano-3-benzazocine according to claim 4.
Claim 20
Dependent Claim
5 words
8-Hydroxy-3,6(eq),11(ax)-trimethyl-1,2,3,4,5,6-hexahydro-11(eq)-[3-(3-methylphenyl)propyl]-2,6-methano-3-benzazocine according to claim 4.
Claim 21
Dependent Claim
5 words
8-Hydroxy-3,6(eq),11(ax)-trimethyl-1,2,3,4,5,6-hexahydro-11(eq)-(5-phenylpentyl)-2,6-methano-3-benzazocine according to claim 5.
References Cited (Backward Citations)
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-06-17 | 1983-12-17 | 1984-06-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-06-17 | 1987-12-17 | 1988-06-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-06-17 | 1991-12-17 | 1992-06-17 | $7700.00 | Window Closed / Lapsed |