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

Details Process for the synthesis of (1h)-benzo[c]quinolizin-3-ones... Process for the synthesis of (1h)-benzo[c]quinolizin-3-ones...

C - Chemistry, Metallurgy

07

D

C07D 455/04 (2006.01)

Patent

CA 2338498

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. Image 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.

Cette invention a trait à un procédé de préparation de dérivés de (1H)-benzo[c]quinolizin-3-ones correspondant à la formule générale (I), lequel procédé ne comprend que trois étapes et n'utilise, comme matières premières, que des composés disponibles dans le commerce ou faciles à élaborer. Les composés correspondant à la formule (I) sont efficaces en tant qu'inhibiteurs de réductases-5 alpha .

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