US4399141A
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US
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5-Alkyl or hydroxyalkyl substituted-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imines and anticonvulsant use thereof
Assignee: Merck and Co Inc
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Filing: 1981-06-12
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Granted: 1983-08-16
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Expires: 2001-06-12
Abstract
Abstract 5-Substituted-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imines, derivatives and pharmaceutically acceptable salts thereof are useful as anticonvulsants.
Inventors
- 👤 Paul Anderson
- 👤 Marcia E. Christy
- 👤 Ben E. Evans
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 09:06
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/04; C07D295/08; C07D295/096; C07C; C07C45/00; C07C45/56; C07D295/10; C07D295/112; C07D295/116; C07D451/00; C07D451/02
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
123 words
A compound of the structural formula ##STR110## or a pharmaceutically acceptable salt thereof wherein: R is (1) hydrogen, (2) C 1-5 alkyl, (3) C 2-5 alkenyl, (4) phenyl-C 1-3 alkyl, (5) halophenyl-C 1-3 alkyl, (6) C 1-3 alkylphenyl-C 1-3 alkyl, (7) C 3-6 cycloalkyl, (8) C 3-6 cycloalkyl-C 1-3 alkyl, (9) di(C 1-3 alkyl)amino-C 1-3 alkyl; or (10) hydroxy; R 1 is (1) hydrogen, (2) C 1-5 alkyl, (3) C 2-5 alkenyl, (4) phenyl-C 1-3 alkyl, (5) C 3-6 cycloalkyl (6) C 3-6 cycloalkyl-C 1-3 alkyl; --CH 2 R 2 is (1) methyl, (2) ethyl or (3) hydroxyethyl; and R 3 and R 4 are independently (1) hydrogen, (2) halogen, (3) C 1-5 alkoxy, (4) trifluoromethylthio, (5) cyano, (6) carboxy, or (7) hydroxy.
Claim 2
Dependent Claim
123 words
A compound of the structural formula ##STR110## or a pharmaceutically acceptable salt thereof wherein: R is (1) hydrogen, (2) C 1-5 alkyl, (3) C 2-5 alkenyl, (4) phenyl-C 1-3 alkyl, (5) halophenyl-C 1-3 alkyl, (6) C 1-3 alkylphenyl-C 1-3 alkyl, (7) C 3-6 cycloalkyl, (8) C 3-6 cycloalkyl-C 1-3 alkyl, (9) di(C 1-3 alkyl)amino-C 1-3 alkyl; or (10) hydroxy; R 1 is (1) hydrogen, (2) C 1-5 alkyl, (3) C 2-5 alkenyl, (4) phenyl-C 1-3 alkyl, (5) C 3-6 cycloalkyl (6) C 3-6 cycloalkyl-C 1-3 alkyl; --CH 2 R 2 is (1) methyl, (2) ethyl or (3) hydroxyethyl; and R 3 and R 4 are independently (1) hydrogen, (2) halogen, (3) C 1-5 alkoxy, (4) trifluoromethylthio, (5) cyano, (6) carboxy, or (7) hydroxy.
Claim 3
Dependent Claim
10 words
The compound of claim 1 wherein R 1 is hydrogen.
Claim 4
Dependent Claim
40 words
The compound of claim 1 wherein R 1 , R 3 and R 4 are hydrogen; R is hydrogen, C 1-5 alkyl, C 2-5 alkenyl or C 3-6 cycloalkyl-C 1-3 alkyl; and --CH 2 R 2 is methyl or ethyl.
Claim 5
Dependent Claim
32 words
The compound of claim 3 wherein R 1 , R 3 and R 4 are hydrogen, R is hydrogen, or C 1-5 alkyl; and --CH 2 R 2 is methyl or ethyl.
Claim 6
Dependent Claim
19 words
The compound of claim 4 which is racemic 5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine, its optically active isomers, or a pharmaceutically acceptable salt thereof.
Claim 7
Dependent Claim
14 words
The compound of claim 4 which is (+)-5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine or a pharmaceutically acceptable salt thereof.
Claim 8
Dependent Claim
139 words
A pharmaceutical composition useful as an anticonvulsant, comprising a pharmaceutical carrier and an effective anticonvulsant amount of a compound of structural formula: ##STR111## or a pharmaceutically acceptable salt thereof wherein: R is (1) hydrogen, (2) C 1-5 alkyl, (3) C 2-5 alkenyl, (4) phenyl-C 1-3 alkyl, (5) halophenyl-C 1-3 alkyl, (6) C 1-3 alkylphenyl-C 1-3 alkyl, (7) C 3-6 cycloalkyl, (8) C 3-6 cycloalkyl-C 1-3 alkyl, (9) di(C 1-3 alkyl)amino-C 1-3 alkyl; or (10) hydroxy; R 1 is (1) hydrogen, (2) C 1-5 alkyl, (3) C 2-5 alkenyl, (4) phenyl-C 1-3 alkyl, (5) C 3-6 cycloalkyl, (6) C 3-6 cycloalkyl-C 1-3 alkyl; --CH 2 R 2 is (1) methyl (2) ethyl or (3) hydroxyethyl; and R 3 and R 4 are independently (1) hydrogen, (2) halogen, (3) C 1-5 alkoxy, (4) trifluoromethylthio, (5) cyano, (6) carboxy, or (7) hydroxy.
Claim 9
Dependent Claim
139 words
A pharmaceutical composition useful as an anticonvulsant, comprising a pharmaceutical carrier and an effective anticonvulsant amount of a compound of structural formula: ##STR111## or a pharmaceutically acceptable salt thereof wherein: R is (1) hydrogen, (2) C 1-5 alkyl, (3) C 2-5 alkenyl, (4) phenyl-C 1-3 alkyl, (5) halophenyl-C 1-3 alkyl, (6) C 1-3 alkylphenyl-C 1-3 alkyl, (7) C 3-6 cycloalkyl, (8) C 3-6 cycloalkyl-C 1-3 alkyl, (9) di(C 1-3 alkyl)amino-C 1-3 alkyl; or (10) hydroxy; R 1 is (1) hydrogen, (2) C 1-5 alkyl, (3) C 2-5 alkenyl, (4) phenyl-C 1-3 alkyl, (5) C 3-6 cycloalkyl, (6) C 3-6 cycloalkyl-C 1-3 alkyl; --CH 2 R 2 is (1) methyl (2) ethyl or (3) hydroxyethyl; and R 3 and R 4 are independently (1) hydrogen, (2) halogen, (3) C 1-5 alkoxy, (4) trifluoromethylthio, (5) cyano, (6) carboxy, or (7) hydroxy.
Claim 10
Dependent Claim
10 words
The composition of claim 7 wherein R 1 is hydrogen.
Claim 11
Dependent Claim
40 words
The composition of claim 7 wherein R 1 , R 3 and R 4 are hydrogen; R is hydrogen, C 1-5 alkyl, C 2-5 alkenyl or C 3-6 cycloalkyl-C 1-3 alkyl; and --CH 2 R 2 is methyl or ethyl.
Claim 12
Dependent Claim
32 words
The composition of claim 9 wherein R 1 , R 3 and R 4 are hydrogen; R is hydrogen, or C 1-5 alkyl; and --CH 2 R 2 is methyl or ethyl.
Claim 13
Dependent Claim
22 words
The pharmaceutical composition of claim 10 wherein the compound is racemic 5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine, its optically active isomers, or a pharmaceutically acceptable salt thereof.
Claim 14
Dependent Claim
17 words
The pharmaceutical composition of claim 10 wherein the compound is (+)-5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine or a pharmaceutically acceptable salt thereof.
Claim 15
Independent Claim
142 words
A method of treating convulsions, comprising administering to a patient in need of such treatment an effective anticonvulsant amount of a compound of structural formula: ##STR112## or a pharmaceutical acceptable salt thereof wherein: R is (1) hydrogen, (2) C 1-5 alkyl, (3) C 2-5 alkenyl, (4) phenyl-C 1-3 alkyl, (5) halophenyl-C 1-3 alkyl, (6) C 1-3 alkylphenyl-C 1-3 alkyl, (7) C 3-6 cycloalkyl, (8) C 3-6 cycloalkyl-C 1-3 alkyl, (9) di(C 1-3 alkyl)amino-C 1-3 alkyl; or (10) hydroxy; R 1 is (1) hydrogen, (2) C 1-5 alkyl (3) C 2-5 alkenyl, (4) phenyl-C 1-3 alkyl, (5) C 3-6 cycloalkyl, (6) C 3-6 cycloalkyl-C 1-3 alkyl; --CH 2 R 2 is (1) methyl, (2) ethyl or (3) hydroxyethyl; and R 3 and R 4 are independently (1) hydrogen, (2) halogen, (3) C 1-5 alkoxy, (4) trifluoromethylthio, (5) cyano, (6) carboxy, or (7) hydroxy.
Claim 16
Independent Claim
142 words
A method of treating convulsions, comprising administering to a patient in need of such treatment an effective anticonvulsant amount of a compound of structural formula: ##STR112## or a pharmaceutical acceptable salt thereof wherein: R is (1) hydrogen, (2) C 1-5 alkyl, (3) C 2-5 alkenyl, (4) phenyl-C 1-3 alkyl, (5) halophenyl-C 1-3 alkyl, (6) C 1-3 alkylphenyl-C 1-3 alkyl, (7) C 3-6 cycloalkyl, (8) C 3-6 cycloalkyl-C 1-3 alkyl, (9) di(C 1-3 alkyl)amino-C 1-3 alkyl; or (10) hydroxy; R 1 is (1) hydrogen, (2) C 1-5 alkyl (3) C 2-5 alkenyl, (4) phenyl-C 1-3 alkyl, (5) C 3-6 cycloalkyl, (6) C 3-6 cycloalkyl-C 1-3 alkyl; --CH 2 R 2 is (1) methyl, (2) ethyl or (3) hydroxyethyl; and R 3 and R 4 are independently (1) hydrogen, (2) halogen, (3) C 1-5 alkoxy, (4) trifluoromethylthio, (5) cyano, (6) carboxy, or (7) hydroxy.
Claim 17
Dependent Claim
10 words
The method of claim 13 wherein R 1 is hydrogen.
Claim 18
Dependent Claim
40 words
The method of claim 14 wherein R 1 , R 3 and R 4 are hydrogen; R is hydrogen, C 1-5 alkyl, C 2-5 alkenyl or C 3-6 cycloalkyl-C 1-3 alkyl; and --CH 2 R 2 is methyl or ethyl.
Claim 19
Dependent Claim
32 words
The method of claim 15 wherein R 1 , R 3 and R 4 are hydrogen; R is hydrogen, or C 1-5 alkyl; and --CH 2 R 2 is methyl or ethyl.
Claim 20
Dependent Claim
21 words
The method of claim 16 wherein the compound is racemic 5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine, its optically active isomers, or a pharmaceutically acceptable salt thereof.
Claim 21
Dependent Claim
16 words
The method of claim 16, wherein the compound is (+)-5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine 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) | 1986-08-15 | 1987-02-14 | 1987-08-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-08-15 | 1991-02-14 | 1991-08-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-08-15 | 1995-02-14 | 1995-08-16 | $7700.00 | Window Closed / Lapsed |