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US 4,399,141 AGranted
5-Alkyl or hydroxyalkyl substituted-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imines and anticonvulsant use thereof
AssigneeMerck & Co., Inc.
InventorsPaul Anderson, Marcia E. Christy, Ben E. Evans
Life of this patent
Estimating the term…
Abstract
5-Substituted-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imines, derivatives and pharmaceutically acceptable salts thereof are useful as anticonvulsants.
Claims18
A compound of the structural formula ##STR110## or a pharmaceutically acceptable salt thereof wherein:
- R is
- (1) hydrogen,
- (2) C.sub.1-5 alkyl,
- (3) C.sub.2-5 alkenyl,
- (4) phenyl-C.sub.1-3 alkyl,
- (5) halophenyl-C.sub.1-3 alkyl,
- (6) C.sub.1-3 alkylphenyl-C.sub.1-3 alkyl,
- (7) C.sub.3-6 cycloalkyl,
- (8) C.sub.3-6 cycloalkyl-C.sub.1-3 alkyl,
- (9) di(C.sub.1-3 alkyl)amino-C.sub.1-3 alkyl;
- or
- (10) hydroxy;
- R.sup.1 is
- (1) hydrogen,
- (2) C.sub.1-5 alkyl,
- (3) C.sub.2-5 alkenyl,
- (4) phenyl-C.sub.1-3 alkyl,
- (5) C.sub.3-6 cycloalkyl
- (6) C.sub.3-6 cycloalkyl-C.sub.1-3 alkyl;
- --CH.sub.2 R.sup.2 is
- (1) methyl,
- (2) ethyl or
- (3) hydroxyethyl;
- and
- R.sup.3 and R.sup.4 are independently
- (1) hydrogen,
- (2) halogen,
- (3) C.sub.1-5 alkoxy,
- (4) trifluoromethylthio,
- (5) cyano,
- (6) carboxy, or
- (7) hydroxy.
29 more elements
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.sub.1-5 alkyl,
- (3) C.sub.2-5 alkenyl,
- (4) phenyl-C.sub.1-3 alkyl,
- (5) halophenyl-C.sub.1-3 alkyl,
- (6) C.sub.1-3 alkylphenyl-C.sub.1-3 alkyl,
- (7) C.sub.3-6 cycloalkyl,
- (8) C.sub.3-6 cycloalkyl-C.sub.1-3 alkyl,
- (9) di(C.sub.1-3 alkyl)amino-C.sub.1-3 alkyl;
- or
- (10) hydroxy;
- R.sup.1 is
- (1) hydrogen,
- (2) C.sub.1-5 alkyl,
- (3) C.sub.2-5 alkenyl,
- (4) phenyl-C.sub.1-3 alkyl,
- (5) C.sub.3-6 cycloalkyl,
- (6) C.sub.3-6 cycloalkyl-C.sub.1-3 alkyl;
- --CH.sub.2 R.sup.2 is
- (1) methyl
- (2) ethyl or
- (3) hydroxyethyl;
- and
- R.sup.3 and R.sup.4 are independently
- (1) hydrogen,
- (2) halogen,
- (3) C.sub.1-5 alkoxy,
- (4) trifluoromethylthio,
- (5) cyano,
- (6) carboxy, or
- (7) hydroxy.
30 more elements
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.sub.1-5 alkyl,
- (3) C.sub.2-5 alkenyl,
- (4) phenyl-C.sub.1-3 alkyl,
- (5) halophenyl-C.sub.1-3 alkyl,
- (6) C.sub.1-3 alkylphenyl-C.sub.1-3 alkyl,
- (7) C.sub.3-6 cycloalkyl,
- (8) C.sub.3-6 cycloalkyl-C.sub.1-3 alkyl,
- (9) di(C.sub.1-3 alkyl)amino-C.sub.1-3 alkyl;
- or
- (10) hydroxy;
- R.sup.1 is
- (1) hydrogen,
- (2) C.sub.1-5 alkyl
- (3) C.sub.2-5 alkenyl,
- (4) phenyl-C.sub.1-3 alkyl,
- (5) C.sub.3-6 cycloalkyl,
- (6) C.sub.3-6 cycloalkyl-C.sub.1-3 alkyl;
- --CH.sub.2 R.sup.2 is
- (1) methyl,
- (2) ethyl or
- (3) hydroxyethyl;
- and
- R.sup.3 and R.sup.4 are independently
- (1) hydrogen,
- (2) halogen,
- (3) C.sub.1-5 alkoxy,
- (4) trifluoromethylthio,
- (5) cyano,
- (6) carboxy, or
- (7) hydroxy.
30 more elements
Dependencies are inferred from the claim text.