Patent US2659618A successfully refreshed from Google Patents.
Patent US4100164A successfully refreshed from Google Patents.
US4100164A
Expired / Lapsed
US
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2,6-Methano-3-benzazocines
Assignee: Sanofi SA
•
Filing: 1976-11-12
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Granted: 1978-07-11
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Expires: 1996-11-12
Abstract
Abstract 6(EQ)-R4-1,2,3,4,5,6-Hexahydro-3-R1-11(ax)-R3-11(eq)-CH2Z-2,6-methano- 3-benzazocines, useful as analgesic agents and narcotic antagonists, and 1-R1-2-Q-4a alpha -R3-5 alpha -R4-1,2,3,4,4a,5,10,10a-octahydro-3,5-ethano- (and 3,5-ethano) benzo[g]quinolines, useful as analgesic agents, prepared by heating, with formic acid in an organic solvent or with certain ammonium formates in the absence of a solvent, certain 1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinolines, the latter prepared by acid catalyzed cyclization of a 3-benzyl-2-azabicyclo[2.2.2]-oct-5-ene.
Inventors
- 👤 William F. Michne
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 08:07
CPC Classifications
C; C07; C07D; C07D221/00; C07D221/02; C07D221/22; C07D221/26; C07D211/00; C07D211/04; C07D211/80; C07D211/82; C07D453/00; C07D453/06
Claims Analysis
Total Claims: 41
Claim 1
Independent Claim
308 words
A compound having the formula ##STR46## where R 1 is hydrogen, lower-alkyl, lower-alkanoyl (only when R 4 is hydrogen), lower-alkenyl, lower-alkynyl, halo-lower-alkenyl, cycloalkyl, cycloalkyl-lower-alkyl, phenyl-lower-alkyl, phenyl-lower-alkyl substituted in the phenyl ring by a single trifluoromethyl or by from one to two members of the group consisting of halogen, lower-alkyl, hydroxy, lower-alkanoyloxy, lower-alkoxy, lower-alkylmercapto, amino, lower-alkanoyl-amino or a single methylenedioxy attached to adjacent carbon atoms, or R 1 is 2- or 3-furylmethyl or such 2- or 3-furylmethyl substituted on the unsubstituted ring carbon atoms by from one to three methyl groups; R 2 , R 2 ', R 2 " and R 2 '" are each hydrogen, or three of them are hydrogen and the fourth is halogen, lower-alkyl, hydroxy, lower-alkanoyloxy, lower-alkoxy, lower-alkylmercapto, trifluoromethyl, nitro, amino, lower-alkanoylamino, lower-alkoxycarbonylamino or phenyl, or two of the adjacent such groups together are methylenedioxy; R 3 is hydrogen or lower-alkyl; R 4 is hydrogen, lower-alkyl, lower-alkoxy-lower-alkyl, hydroxy-lower-alkyl, lower-alkylthio-lower-alkyl, lower-alkylsulfinyl-lower-alkyl, phenylthio-lower-alkyl, phenylsulfinyl-lower-alkyl, lower-alkenyl or halo-lower-alkyl, or R 3 and R 4 together are divalent lower-alkylene, --(CH 2 ) n --, where n is one of the integers 3 or 4; R 8 is hydrogen or lower-alkyl; and Y is carboxy, cyano, carbo-lower-alkoxy, COR 5 , COO-lower-alkylene-cycloalkyl, COO-lower-alkylene-phenyl, or a group of the formula: ##STR47## where R 5 and R 6 are the same or different members selected from the group consisting of hydrogen, lower-alkyl, cycloalkyl-lower-alkyl, phenyl or phenyl-lower-alkyl; and R 7 is hydrogen, lower-alkanoyl, benzoyl, or benzoyl substituted by a single trifluoromethyl or by one to three sterically compatible members of the group consisting of lower-alkyl, lower-alkoxy, hydroxy or halo, and wherein cycloalkyl, all occurrences, is a group having from 3 to 7 carbon atoms or is alkyl-substituted cycloalkyl having a total of from 3 to 8 carbon atoms, 3 to 7 of which are cycloalkyl ring carbon atoms, or an acid-addition salt thereof.
Claim 2
Dependent Claim
308 words
A compound having the formula ##STR46## where R 1 is hydrogen, lower-alkyl, lower-alkanoyl (only when R 4 is hydrogen), lower-alkenyl, lower-alkynyl, halo-lower-alkenyl, cycloalkyl, cycloalkyl-lower-alkyl, phenyl-lower-alkyl, phenyl-lower-alkyl substituted in the phenyl ring by a single trifluoromethyl or by from one to two members of the group consisting of halogen, lower-alkyl, hydroxy, lower-alkanoyloxy, lower-alkoxy, lower-alkylmercapto, amino, lower-alkanoyl-amino or a single methylenedioxy attached to adjacent carbon atoms, or R 1 is 2- or 3-furylmethyl or such 2- or 3-furylmethyl substituted on the unsubstituted ring carbon atoms by from one to three methyl groups; R 2 , R 2 ', R 2 " and R 2 '" are each hydrogen, or three of them are hydrogen and the fourth is halogen, lower-alkyl, hydroxy, lower-alkanoyloxy, lower-alkoxy, lower-alkylmercapto, trifluoromethyl, nitro, amino, lower-alkanoylamino, lower-alkoxycarbonylamino or phenyl, or two of the adjacent such groups together are methylenedioxy; R 3 is hydrogen or lower-alkyl; R 4 is hydrogen, lower-alkyl, lower-alkoxy-lower-alkyl, hydroxy-lower-alkyl, lower-alkylthio-lower-alkyl, lower-alkylsulfinyl-lower-alkyl, phenylthio-lower-alkyl, phenylsulfinyl-lower-alkyl, lower-alkenyl or halo-lower-alkyl, or R 3 and R 4 together are divalent lower-alkylene, --(CH 2 ) n --, where n is one of the integers 3 or 4; R 8 is hydrogen or lower-alkyl; and Y is carboxy, cyano, carbo-lower-alkoxy, COR 5 , COO-lower-alkylene-cycloalkyl, COO-lower-alkylene-phenyl, or a group of the formula: ##STR47## where R 5 and R 6 are the same or different members selected from the group consisting of hydrogen, lower-alkyl, cycloalkyl-lower-alkyl, phenyl or phenyl-lower-alkyl; and R 7 is hydrogen, lower-alkanoyl, benzoyl, or benzoyl substituted by a single trifluoromethyl or by one to three sterically compatible members of the group consisting of lower-alkyl, lower-alkoxy, hydroxy or halo, and wherein cycloalkyl, all occurrences, is a group having from 3 to 7 carbon atoms or is alkyl-substituted cycloalkyl having a total of from 3 to 8 carbon atoms, 3 to 7 of which are cycloalkyl ring carbon atoms, or an acid-addition salt thereof.
Claim 3
Dependent Claim
205 words
A compound having the formula: ##STR48## where R 1 is hydrogen, lower-alkyl, lower-alkenyl, lower-alkynyl, cycloalkyl-lower-alkyl, phenyl-lower-alkyl or 2- or 3-furylmethyl, or such 2- or 3-furylmethyl substituted on the unsubstituted ring carbon atoms by from one to three methyl groups; R 2 , R 2 ', R 2 " and R 2 '" are each hydrogen, or three of them are hydrogen and the fourth is hydroxy or lower-alkoxy; R 3 is hydrogen or lower-alkyl; R 4 is lower-alkyl, lower-alkoxy-lower-alkyl, hydroxy-lower-alkyl, phenylthio-lower-alkyl or lower-alkenyl; Y is carboxy, carbo-lower-alkoxy, COR 5 , COO-lower-alkylene-cycloalkyl, COO-lower-alkylene-phenyl, or a group of the formula ##STR49## where R 5 and R 6 are the same or different members selected from the group consisting of hydrogen, lower-alkyl, phenyl or phenyl-lower-alkyl; R 8 is hydrogen or lower-alkyl; and R 7 is hydrogen, lower-alkanoyl, benzoyl or benzoyl substituted by a single trifluoromethyl or by from one to three sterically compatible members of the group consisting of lower-alkyl, lower-alkoxy, hydroxy or halo, and wherein cycloalkyl, all occurrences, is a group having from 3 to 7 carbon atoms or is alkyl-substituted cycloalkyl having a total of from 3 to 8 carbon atoms, 3 to 7 of which are cycloalkyl ring carbon atoms, or an acid-addition salt thereof.
Claim 4
Dependent Claim
205 words
A compound having the formula: ##STR48## where R 1 is hydrogen, lower-alkyl, lower-alkenyl, lower-alkynyl, cycloalkyl-lower-alkyl, phenyl-lower-alkyl or 2- or 3-furylmethyl, or such 2- or 3-furylmethyl substituted on the unsubstituted ring carbon atoms by from one to three methyl groups; R 2 , R 2 ', R 2 " and R 2 '" are each hydrogen, or three of them are hydrogen and the fourth is hydroxy or lower-alkoxy; R 3 is hydrogen or lower-alkyl; R 4 is lower-alkyl, lower-alkoxy-lower-alkyl, hydroxy-lower-alkyl, phenylthio-lower-alkyl or lower-alkenyl; Y is carboxy, carbo-lower-alkoxy, COR 5 , COO-lower-alkylene-cycloalkyl, COO-lower-alkylene-phenyl, or a group of the formula ##STR49## where R 5 and R 6 are the same or different members selected from the group consisting of hydrogen, lower-alkyl, phenyl or phenyl-lower-alkyl; R 8 is hydrogen or lower-alkyl; and R 7 is hydrogen, lower-alkanoyl, benzoyl or benzoyl substituted by a single trifluoromethyl or by from one to three sterically compatible members of the group consisting of lower-alkyl, lower-alkoxy, hydroxy or halo, and wherein cycloalkyl, all occurrences, is a group having from 3 to 7 carbon atoms or is alkyl-substituted cycloalkyl having a total of from 3 to 8 carbon atoms, 3 to 7 of which are cycloalkyl ring carbon atoms, or an acid-addition salt thereof.
Claim 5
Dependent Claim
10 words
A compound according to claim 2 where Y is carboxy.
Claim 6
Dependent Claim
10 words
A compound according to claim 2 where Y is carbo-lower-alkoxy.
Claim 7
Dependent Claim
10 words
A compound according to claim 2 where Y is lower-alkanoyl.
Claim 8
Dependent Claim
12 words
A compound according to claim 2 where Y is the group ##STR50##
Claim 9
Dependent Claim
6 words
1-Methyl-5α-ethyl-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylic acid according to claim 3.
Claim 10
Dependent Claim
6 words
1-Benzyl-5α-ethyl-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylic acid according to claim 3.
Claim 11
Dependent Claim
6 words
1-Methyl-5α-ethyl-7-hydroxy-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylic acid according to claim 3.
Claim 12
Dependent Claim
6 words
1,5α-Dimethyl-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylic acid according to claim 3.
Claim 13
Dependent Claim
6 words
5α-Ethyl-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylic acid according to claim 3.
Claim 14
Dependent Claim
6 words
Ethyl 1-benzyl-5α-methyl-7-methoxy-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylate according to claim 4.
Claim 15
Dependent Claim
7 words
Methyl 1,5α-dimethyl-7-hydroxy-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline -3-carboxylate according to claim 4.
Claim 16
Dependent Claim
6 words
Ethyl 1-methyl-5α-propyl-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylate according to claim 4.
Claim 17
Dependent Claim
6 words
Ethyl 1-methyl-5α-ethyl-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylate according to claim 4.
Claim 18
Dependent Claim
6 words
Methyl 1,5α-dimethyl-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylate according to claim 4.
Claim 19
Dependent Claim
6 words
Ethyl 5α-ethyl-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylate according to claim 4.
Claim 20
Dependent Claim
6 words
Ethyl 1-cyclopropylmethyl-5α-ethyl-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylate according to claim 4.
Claim 21
Dependent Claim
6 words
Ethyl 4aα,5α-dimethyl-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylate according to claim 4.
Claim 22
Dependent Claim
5 words
1-Benzyl-3-acetyl-5α-ethyl-1,2,3,4,4a,5,10,10a-octahyro-2,5-methanobenzo[g]quinoline according to claim 5.
Claim 23
Dependent Claim
5 words
1,4aα-Dimethyl-3-acetyl-5α-ethyl-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline according to claim 5.
Claim 24
Dependent Claim
5 words
1-Benzyl-3-acetyl-5α-methyl-7-methoxy-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline according to claim 5.
Claim 25
Dependent Claim
5 words
1-Benzyl-3-acetyl-5α-methyl-7-hydroxy-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline according to claim 5.
Claim 26
Dependent Claim
5 words
3-Acetyl-5α-methyl-7-hydroxy-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline according to claim 5.
Claim 27
Dependent Claim
5 words
1-Cyclopropylmethyl-3-acetyl-5α-ethyl-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline according to claim 5.
Claim 28
Dependent Claim
5 words
1-Methyl-3-acetyl-5α-ethyl-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline according to claim 5.
Claim 29
Dependent Claim
5 words
1-Methyl-3-butyryl-5α-ethyl-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline according to claim 5.
Claim 30
Dependent Claim
5 words
1-Methyl-3-acetyl-5α-ethyl-7-hydroxy-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline according to claim 5.
Claim 31
Dependent Claim
5 words
1-Methyl-3-(2-hydroxy-2-propyl)-5α-propyl-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline according to claim 6.
Claim 32
Dependent Claim
5 words
1Methyl-3-(2-hydroxy-2-propyl)-5α-ethyl-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline according to claim 6.
Claim 33
Dependent Claim
5 words
1,5α-Dimethyl-3-(2-hydroxy-2-propyl)-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline according to claim 6.
Claim 34
Dependent Claim
5 words
1-Methyl-3-(2-hydroxy-2-propyl)-5α-ethyl-7-hydroxy-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline accroding to claim 6.
Claim 35
Dependent Claim
5 words
1-Cyclopropylmethyl-3-(2-hydroxy-2-propyl)-5α-ethyl-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline according to claim 6.
Claim 36
Dependent Claim
5 words
1-(2-Phenylethyl)-3-(2-hydroxy-2-propyl)-5α-ethyl-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline according to claim 6.
Claim 37
Dependent Claim
5 words
1-Methyl-3-(2-hydroxy-2-pentyl)-5α-ethyl-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline according to claim 6.
Claim 38
Dependent Claim
5 words
1,4aα-Dimethyl-3-(2-hydroxy-2-propyl)-5α-ethyl-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline according to claim 6.
Claim 39
Dependent Claim
5 words
1-Methyl-3-hydroxymethyl-5α-ethyl-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline according to claim 6.
Claim 40
Dependent Claim
5 words
1-Methyl-3-(1-hydroxyethyl)-5α-ethyl-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline according to claim 6.
Claim 41
Dependent Claim
5 words
4aα,5α-Dimethyl-3-(2-hydroxy-2-propyl)-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline according to claim 6.
References Cited (Backward Citations)
US2524856A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1981-07-10 | 1982-01-09 | 1982-07-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-07-10 | 1986-01-09 | 1986-07-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-07-10 | 1990-01-09 | 1990-07-11 | $7700.00 | Window Closed / Lapsed |