CA2338498C — Process for the synthesis of (1h)-benzo[c]quinolizin-3-ones derivatives

USPTO Abstract

The present invention refers to a process for the preparation of (1H)-benzo[c]quinolizin-3-ones derivatives of general formula (I) which involves the three steps shown below and the use, as starting products, of commercially available, or easily preparable, compounds. The compounds of formula (I) are useful as inhibitors of 5.alpha.-reductases. wherein R1, R2, R3, R4, R5, are the same or different, and are selected from the group consisting of: H, C1-8alkyl, C2-8alkenyl, C2-8alkinyl, cycloalkyl, aryl, heterocycle, halogen, CN, azide, NRR', C1-8alkylamino, arylamino, C1-8alkyloxy, aryloxy, COOR, and CONRR' wherein R and R', are the same or different, and are selected from the group consisting of: H, C1-8alkyl, cycloalkyl, aryl, heterocycle, and arylC1-8alkyl; Q is selected from the group consisting of: a single bond, C1-8alkyl, C2-8alkenyl, C2-8alkinyl, cycloalkyl, CO, CONR, and NR, wherein R is as above defined; W is selected from the group consisting of: H, C1-8alkyl, C2-8 alkenyl, C2-8alkinyl, cycloalkyl, trifluoromethyl, C1-8alkoxy, C1-8 alkoxy-C1-8alkyl, arylC1-8alkyl, aryl, aryloxy, arylamino, C1-8alkylcarbonyl, arylcarbonyl, arylcarboxyl, arylcarboxyamide, halogen, CN, NRR', C1-8alkylamino, and heterocycle wherein the groups alkyl, alkenyl, alkinyl, cycloalkyl, aryl, and heterocycle, can be substituted; n is an integer comprised between 1 and 4; and X is selected from hydrochloride, sulphate, citrate, formiate and phosphate.