Cyclohepta[b][1,4]diazepino[6,7,1-hi]indoles and derivatives
View Patent ↗This invention provides compounds of the formula: wherein R 1 and R 2 are each, independently, H, alkyl, cycloalkyl, —CH 2 -cycloalkyl, alkoxy, halogen, fluorinated alkyl, —CN, —NH—SO 2 -alkyl, —SO 2 —NH-alkyl, alkyl amide, amino, alkylamino, dialkylamino, fluorinated alkoxy, acyl, or phenoyl or thiophenoyl; R 3 and R 4 are each, independently, H, alkyl or cycloalkyl; R 5 is H or alkyl; R 6 is H or; and the dashed line indicates an optional double bond; or a pharmaceutically acceptable salt thereof, and pharmaceutical compositions and methods utilizing these compounds for the treatment or prevention of disorders including obsessive-compulsive disorder, depression, anxiety, generalized anxiety disorder, schizophrenia, migraine, sleep disorders, eating disorders, obesity, epilepsy, and spinal cord injury.
1. A compound of the formula:
wherein:
R 1 and R 2 are each, independently, hydrogen, alkyl of 1-6 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, —CH 2 -cycloalkyl of 3 to 7 carbon atoms, alkoxy of 1-6 carbon atoms, halogen, fluorinated alkyl of 1 to 6 carbon atoms, —CN, —NH—SO 2 -alkyl of 1-6 carbon atoms, —SO 2 -NH-alkyl of 1-6 carbon atoms, alkyl amide of 1-6 carbon atoms, amino, alkylamino of 1-6 carbon atoms, dialkylamino of 1-6 carbon atoms per alkyl moiety, fluorinated alkoxy of 1-6 carbon atoms, acyl of 2-7 carbon atoms, or phenoyl or thiophenoyl;
R 3 and R 4 are each, independently, hydrogen, C 1 -C 6 alkyl or cycloalkyl of 3 to 7 carbon atoms;
R 5 is hydrogen or C 1 -C 6 alkyl;
R 6 is hydrogen or C 1 -C 6 alkyl; and
wherein the dashed line indicates an optional double bond;
or a pharmaceutically acceptable salt thereof.
2. A compound of claim 1 which is 1,2,3,4,9,10,11,12-Octahydro-8H-cyclohepta[b][1,4]diazepino[6,7,1-hi]indole or a pharmaceutically acceptable salt thereof.
3. A compound of claim 1 which is 1,2,3,4,8,9,10,11,12,12a-decahydro-7bH-cyclohepta[b][1,4]diazepino[6,7,1-hi]indole or a pharmaceutically acceptable salt thereof.
4. A pharmaceutical composition comprising a pharmaceutically effective amount of a compound of claim 1 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier or excipient.
5. A method of treatment of obsessive-compulsive disorder in a mammal, the method comprising administering to a mammal in need thereof a pharmaceutically effective amount of a compound of claim 1 , or a pharmaceutically acceptable salt thereof.
6. A method of treatment of depression in a mammal, the method comprising administering to a mammal in need thereof a pharmaceutically effective amount of a compound of claim 1 , or a pharmaceutically acceptable salt thereof.
7. A method of treatment of anxiety in a mammal, the method comprising administering to a mammal in need thereof a pharmaceutically effective amount of a compound of claim 1 , or a pharmaceutically acceptable salt thereof.