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US4148794A Expired / Lapsed US ⏱️ 0.0 years remaining

Lower-alkyl 3-R5 CO-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylates

Assignee: Sanofi SA
•
Filing: 1978-02-16
•
Granted: 1979-04-10
•
Expires: 1998-02-16
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Abstract

Abstract Lower-alkyl 1-R1-3-R5CO-4a alpha -R3-5 alpha -R4-6-R2''-7-R2-8-R2'-9-R2'''-1,2,3,4,4a,5,10,10a-octahydro-2,5-methan obenzo[g]quinoline-3-carboxylates, useful as intermediates for the preparation of 3-R1-6(eq)-R4-7-R2''-8-R2-9-R2'-10-R2'''-11(ax)-R3-11(eq)-CH2CH2COR5-1 ,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocines, useful as analgesics and narcotic antagonists, are prepared by acylation of an appropriate lower-alkyl 1-R1-4a alpha -R3-5 alpha C-R4-6-R2''-7-R2-8-R2'-9-R2'''-1,2,3,4,4a,5,10,10a-octahydro-2,5-metha nobenzo[g]quinoline-3-carboxylate or carboxylation of an appropriate 1-R1-3-COR5''-4 alpha -R3-5 alpha -R4-6-R2''-7-R2-8-R2'-9-R2'''-1,2,3,4,4a,5,10,10a-octahydro-2,5-methan obenzo[g]quinoline.

Inventors

  • 👤 Thomas R. Lewis
  • 👤 William F. Michne

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-06 14:43
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/04; C07D211/80; C07D211/82; A; A61; A61P; A61P25/00; A61P25/04; C07D221/00; C07D221/02; C07D221/04; C07D221/06; C07D221/08; C07D221/22; C07D221/26; C07D453/00; C07D453/06; C07D471/00; C07D471/02; C07D471/08

Claims Analysis

Total Claims: 35
Claim 1
Independent Claim 262 words
A compound having the formula: ##STR15## where R 1 is hydrogen; lower-alkyl; lower-alkenyl; lower-alkynyl; halo-lower-alkenyl; lower-cycloalkyl; lower-cycloalkyl-lower-alkyl; 2- or 3-furylmethyl; or such 2- or 3-furylmethyl substituted on the ring carbon atoms by from one to three methyl groups; phenyl-lower-alkyl; or phenyl-lower-alkyl substituted in the phenyl ring by methylenedioxy or from one to two members of the group consisting of halogen, lower-alkyl, hydroxy, lower-alkanoyloxy, lower-alkoxy, lower-alkylmercapto, trifluoromethyl, amino and lower-alkanoylamino; 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-alkyl-sulfinyl-lower-alkyl, phenylthio-lower-alkyl, phenyl-sulfinyl-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 5 is lower-alkyl; lower-alkylthio-lower-alkyl; lower-alkoxy-lower-alkyl; lower-alkoxy; lower-cycloalkyl; lower-cycloalkyl-lower-alkyl; 2- or 3-furyl; 2- or 3-furyl-(CH 2 ) m , where m is an integer from 2 to 4; or such 2- or 3-furyl or 2- or 3-furyl-(CH 2 ) m substituted on the unsubstituted ring carbon atoms by from one to three methyl groups; phenyl; phenyl-(CH 2 ) m ; or phenyl or phenyl-(CH 2 ) m substituted in the phenyl ring by methylenedioxy or from one to two members of the group consisting of halogen, lower-alkyl, hydroxy, lower-alkanoyloxy, lower-alkoxy, lower-alkylmercapto, trifluoromethyl, amino and lower-alkanoylamino; and Alk is lower-alkyl.
Claim 2
Dependent Claim 262 words
A compound having the formula: ##STR15## where R 1 is hydrogen; lower-alkyl; lower-alkenyl; lower-alkynyl; halo-lower-alkenyl; lower-cycloalkyl; lower-cycloalkyl-lower-alkyl; 2- or 3-furylmethyl; or such 2- or 3-furylmethyl substituted on the ring carbon atoms by from one to three methyl groups; phenyl-lower-alkyl; or phenyl-lower-alkyl substituted in the phenyl ring by methylenedioxy or from one to two members of the group consisting of halogen, lower-alkyl, hydroxy, lower-alkanoyloxy, lower-alkoxy, lower-alkylmercapto, trifluoromethyl, amino and lower-alkanoylamino; 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-alkyl-sulfinyl-lower-alkyl, phenylthio-lower-alkyl, phenyl-sulfinyl-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 5 is lower-alkyl; lower-alkylthio-lower-alkyl; lower-alkoxy-lower-alkyl; lower-alkoxy; lower-cycloalkyl; lower-cycloalkyl-lower-alkyl; 2- or 3-furyl; 2- or 3-furyl-(CH 2 ) m , where m is an integer from 2 to 4; or such 2- or 3-furyl or 2- or 3-furyl-(CH 2 ) m substituted on the unsubstituted ring carbon atoms by from one to three methyl groups; phenyl; phenyl-(CH 2 ) m ; or phenyl or phenyl-(CH 2 ) m substituted in the phenyl ring by methylenedioxy or from one to two members of the group consisting of halogen, lower-alkyl, hydroxy, lower-alkanoyloxy, lower-alkoxy, lower-alkylmercapto, trifluoromethyl, amino and lower-alkanoylamino; and Alk is lower-alkyl.
Claim 3
Dependent Claim 54 words
A compound according to claim 1 where R 1 is lower-alkyl, cycloalkyl-lower-alkyl or phenyl-lower-alkyl; R 2 is lower-alkoxy or hydrogen; R 2 ', R 2 " and R 2 '" are each hydrogen; R 3 is hydrogen or lower-alkyl; and R 4 is lower-alkyl, or R 3 and R 4 together are divalent lower-alkylene.
Claim 4
Dependent Claim 46 words
A compound according to claim 2 where R 5 is lower-alkyl, lower-alkylthio-lower-alkyl, lower-alkoxy, cycloalkyl, cycloalkyl-lower-alkyl, 2-furyl, 2-furyl-(CH 2 ) m , phenyl, phenyl-(CH 2 ) m , or phenyl or phenyl-(CH 2 ) m substituted in the phenyl ring by from one to three lower-alkyl groups.
Claim 5
Dependent Claim 11 words
A compound according to claim 3 where R 5 is lower-alkyl.
Claim 6
Dependent Claim 11 words
A compound according to claim 3 where R 5 is lower-alkylthio-lower-alkyl.
Claim 7
Dependent Claim 15 words
A compound according to claim 3 where R 5 is phenyl-(CH 2 ) m .
Claim 8
Dependent Claim 11 words
A compound according to claim 3 where R 5 is lower-alkoxy.
Claim 9
Dependent Claim 11 words
A compound according to claim 3 where R 5 is 2-furyl.
Claim 10
Dependent Claim 15 words
A compound according to claim 3 where R 5 is 2-furyl-(CH 2 ) m .
Claim 11
Dependent Claim 11 words
A compound according to claim 3 where R 5 is cycloalkyl-lower-alkyl.
Claim 12
Dependent Claim 20 words
A compound according to claim 3 where R 5 is phenyl or phenyl substituted in the phenyl ring by lower-alkyl.
Claim 13
Dependent Claim 6 words
Ethyl 7-methoxy-1,4aα,5α-trimethyl-3-(1-oxohexyl)-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylate according to claim 4.
Claim 14
Dependent Claim 6 words
Ethyl 7-methoxy-1,4aα,5α-trimethyl-3-(4-methyl-1-oxopentyl)-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylate according to claim 4.
Claim 15
Dependent Claim 6 words
Ethyl 7-methoxy-1,4aα,5α-trimethyl-3-(1-oxobutyl)-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 7-methoxy-1,5α-dimethyl-3-(1-oxopentyl)-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 7-methoxy-1,4aα,5α-trimethyl-3-(3-methyl-1-oxobutyl)-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
Ethyl 7-methoxy-1,4aα,5α-trimethyl-3-(1-oxopropyl)-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 7-methoxy-1,5α-dimethyl-3-(1-oxoethyl)-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-7-methoxy-4aα,5α-dimethyl-3-(1-oxopentyl)-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 7-methoxy-1,4aα,5α-trimethyl-3-(1-oxoethyl)-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylate according to claim 4.
Claim 22
Dependent Claim 6 words
Ethyl 7-methoxy-1,5α-dimethyl-3-(1-oxohexyl)-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylate according to claim 4.
Claim 23
Dependent Claim 6 words
Ethyl 7-methoxy-1,4aα,5α-trimethyl-3-(1-oxoheptyl)-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylate according to claim 4.
Claim 24
Dependent Claim 6 words
Ethyl 7-methoxy-1,5α-dimethyl-3-(4-methyl-1-oxopentyl)-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylate according to claim 4.
Claim 25
Dependent Claim 6 words
Ethyl 7-methoxy-1,4aα,5α-trimethyl-3-(1-oxopentyl)-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylate according to claim 4.
Claim 26
Dependent Claim 6 words
Ethyl 7-methoxy-1,4aα,5α-trimethyl-3-[(4-methylthio)-1-oxobutyl]-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylate according to claim 5.
Claim 27
Dependent Claim 6 words
Ethyl 7-methoxy-1,4aα,5α-trimethyl-3-(1-oxo-3-phenylpropyl)-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylate according to claim 6.
Claim 28
Dependent Claim 6 words
Diethyl 7-methoxy-1,4aα,5α-trimethyl-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3,3-dicarboxylate according to claim 7.
Claim 29
Dependent Claim 6 words
Ethyl 7-methoxy-1,4aα,5α-trimethyl-3-(2-furoyl)-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylate according to claim 8.
Claim 30
Dependent Claim 6 words
Ethyl 7-methoxy-1,4aα,5α-trimethyl-3-[3-(2-furyl)-1-oxopropyl]-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylate according to claim 9.
Claim 31
Dependent Claim 6 words
Ethyl 7-methoxy-1,4aα,5α-trimethyl-3-(1-oxo-3-cyclopentylpropyl)-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylate according to claim 10.
Claim 32
Dependent Claim 6 words
Ethyl 7-methoxy-1,4aα,5α-trimethyl-3-(1-oxo-3-cyclopropyl)-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylate according to claim 10.
Claim 33
Dependent Claim 6 words
Ethyl 7-methoxy-1,4aα,5α-trimethyl-3-(1-oxo-3-cyclobutylpropyl)-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylate according to claim 10.
Claim 34
Dependent Claim 6 words
Ethyl 7-methoxy-1,4aα,5α-trimethyl-3-(4-methylbenzoyl)-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylate according to claim 11.
Claim 35
Dependent Claim 6 words
Ethyl 7-methoxy-1,4aα,5α-trimethyl-3-(3-methylbenzoyl)-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylate according to claim 11.

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) 1982-04-09 1982-10-09 1983-04-10 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-04-09 1986-10-09 1987-04-10 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1990-04-09 1990-10-09 1991-04-10 $7700.00 Window Closed / Lapsed

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