Benzo[c]quinolizine derivatives, their preparation and use as 5α-reductases inhibitors

Benzo[c]-quinolizine compounds of formula (I)

• wherein:
• R1, R2, R3, R4, R6, same or different, are chosen in the group consisting of:
• H, C1-8alkyl, C2-8alkenyl, C2-8alkinyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, norbornane, canphane, adamantane, phenyl, naphthyl, saturated or aromatic heterocycle containing one or more N atoms, halogen, CN, azide, NRR′, C1-8alkylamino, arylamino, C1-8alkyloxy, aryloxy, COOR, CONRR′ wherein R and R′, same or different, are chosen in the group consisting of:
• H, C1-8alkyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, norbornane, canphane, adamantane, phenyl, naphthyl, saturated or aromatic heterocycle containing one or more N atoms, arylC1-8alkyl;
• R5 is chosen in the group consisting of:
• H, C1-8alkyl, COOR, CN, phenyl, naphthyl, saturated or aromatic heterocycle containing one or more N atoms;
• X is chosen in the group consisting of:
• O, C(═O)R, COOR, NO2, CONR′R wherein R and R′ are as above defined;
• Q is chosen in the group consisting of:
• simple bond, C1-8alkyl, C2-8alkenyl, C2-8alkinyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, norbornane, canphane, adamantane, CO, CONR, NR, wherein R is as above defined;
• W is chosen in the group consisting of:
• H, C1-8alkyl, C2-8alkenyl, C2-8alkinyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, norbornane, canphane, adamantane, trifluoromethyl, C1-8alkoxy, C1-8alkoxy-C1-8alkyl, arylC1-8alkyl, phenyl, naphthyl aryloxy, arylamino, C1-8alkylcarbonyl, arylcarbonyl, halogen, CN, NRR′, C1-8alkylamino, saturated or aromatic heterocycle containing one or more N atoms, wherein the groups alkyl, alkenyl, alkinyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, norbornane, canphane, adamantane, phenyl, naphthyl, saturated or aromatic heterocycle containing one or more N atoms can be substitued by halogen, OR, phenyl, NRR′, CN, COOR, CONRR′, C1-8alkyl (wherein R and R′ are as above defined);
• n is an integer comprised between 1 and 4;
• the symbol ------ means that the corresponding bonds a, b, c, d e, f, and g can be simple or double bonds;
• with the proviso that when b or f are a double bond then the group R5 is absent;
• and with the proviso that the following two compounds are excluded from the claim:
• 4-carbonitril-2,3-dihydro-(1H)-benzo[c]quinolizin-3-one and 3,4-dihydro-1-phenyl-4aH-benzo[c]quinolizin-3-one;
• their pharmaceutically acceptable salts or esters.