Claims
- 1. 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.
- 2. The compound of claim 1 wherein R.sup.1 is hydrogen.
- 3. The compound of claim 1 wherein R.sup.1, R.sup.3 and R.sup.4 are hydrogen; R is hydrogen, C.sub.1-5 alkyl, C.sub.2-5 alkenyl or C.sub.3-6 cycloalkyl-C.sub.1-3 alkyl; and --CH.sub.2 R.sup.2 is methyl or ethyl.
- 4. The compound of claim 3 wherein R.sup.1, R.sup.3 and R.sup.4 are hydrogen, R is hydrogen, or C.sub.1-5 alkyl; and --CH.sub.2 R.sup.2 is methyl or ethyl.
- 5. 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.
- 6. 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.
- 7. 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.
- 8. The composition of claim 7 wherein R.sup.1 is hydrogen.
- 9. The composition of claim 7 wherein R.sup.1, R.sup.3 and R.sup.4 are hydrogen; R is hydrogen, C.sub.1-5 alkyl, C.sub.2-5 alkenyl or C.sub.3-6 cycloalkyl-C.sub.1-3 alkyl; and --CH.sub.2 R.sup.2 is methyl or ethyl.
- 10. The composition of claim 9 wherein R.sup.1, R.sup.3 and R.sup.4 are hydrogen; R is hydrogen, or C.sub.1-5 alkyl; and --CH.sub.2 R.sup.2 is methyl or ethyl.
- 11. 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.
- 12. 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.
- 13. 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.
- 14. The method of claim 13 wherein R.sup.1 is hydrogen.
- 15. The method of claim 14 wherein R.sup.1, R.sup.3 and R.sup.4 are hydrogen; R is hydrogen, C.sub.1-5 alkyl, C.sub.2-5 alkenyl or C.sub.3-6 cycloalkyl-C.sub.1-3 alkyl; and --CH.sub.2 R.sup.2 is methyl or ethyl.
- 16. The method of claim 15 wherein R.sup.1, R.sup.3 and R.sup.4 are hydrogen; R is hydrogen, or C.sub.1-5 alkyl; and --CH.sub.2 R.sup.2 is methyl or ethyl.
- 17. 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.
- 18. 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.
BACKGROUND OF THE INVENTION
This is a continuation-in-part of copending application Ser. No. 74,367, filed Sept. 10, 1979 abandoned which in turn is a continuation-in-part of Ser. No. 912,772, filed June 5, 1978, (now abandoned) which in turn is a continuation-in-part of application, Ser. No. 834,639, filed Sept. 19, 1977, also abandoned.
US Referenced Citations (4)
Number |
Name |
Date |
Kind |
3892756 |
Nedelec et al. |
Jul 1975 |
|
4052508 |
Anderson et al. |
Oct 1977 |
|
4064139 |
Anderson et al. |
Dec 1977 |
|
4123546 |
Haire |
Oct 1978 |
|
Non-Patent Literature Citations (1)
Entry |
Clineschmidt et al., Drug Devel. Res., 2:123-134, 147-163 (1982). |
Continuation in Parts (3)
|
Number |
Date |
Country |
Parent |
74367 |
Sep 1979 |
|
Parent |
912772 |
Jun 1978 |
|
Parent |
834639 |
Sep 1977 |
|