Patent DK-554181-A (DK)
Inventor: BRAESTRUP C T
IPC: C07D471/04
Filed: 1981-12-14
Abstract: β-Carboline derivatives of the general formula I, <IMAGE> where: Y is O; NOR1, where R1 is H, a lower alkyl group an aryl or aralkyl group, COR2, where R2 is a lower alkyl group; CHCOOR3, where R3 is H or a lower alkyl group; <IMAGE> where R4 and R5 are each H, a lower alkyl group, an aryl or aralkyl group or CONR6R7, where R6 and R7 are each H or a lower alkyl group, or where R4 and R5, together with the neighbouring nitrogen atom form a part of a 5- or 6- membered heterocyclic ring which can additionally contain an O atom or up to 3 N atoms and can optionally be substituted by a lower alkyl group; Z is H; a lower alkyl group, an aryl or aralkyl group which is optionally substituted by a COOR8 group, where R8 is a lower alkyl group, or a CONR9R10 group, where R9 and R10 are each H or a lower alkyl group; a group which has the formula NR11CR12R13, where R11 is H or a double bond, and R12 is O when R11 is H and is NR14R15 when R11 is a double bond, with R14 and R15 each being H, a lower alkyl group, OH or a lower alkoxy group, and where R13 is H or a lower alkyl group, and where Y and Z, together with the neighbouring C atom, can be a part of a 5- or 6- membered heterocyclic ring containing an O atom, an S atom, both an O atom and an N atom, both an S atom and N atom or up to 4 N atoms, with the heterocyclic ring being optionally substituted by a lower alkyl group, a cycloalkyl or aryl group or OH; RA is H; a halogen atom; NO2; CH3, CF3; CN; NR16R17 or NHCOR16, where R16 and R17 are each H or a lower alkyl group or an aralkyl or cycloalkyl group, with it being possible for the said alkyl, aralkyl and cycloalkyl groups to be substituted by halogen, hydroxyl, SH, SR18, COOR18, nitrile, CONR18R19, CHOR18OR19 or CHSR18SR19, where R18 and R19 are each H or a lower alkyl group having up to 3 carbon atoms, or where R16 and R17 can together form a saturated or unsaturated heterocyclic ring having from 3 to 7 members, which ring is optionally substituted by a lower alkyl group having up to 3 carbon atoms, S, O, OR18, SR18 or NR18R19, in which ring a C atom can be replaced with S, O or NR18, where R18 has the abovementioned meaning; OR20, where R20 is an unsubstituted or halogen- substituted alkyl, aryl or aralkyl group; SO2R21, where R21 is a lower alkyl group; SR22, where R22 is a lower alkyl group; SCH2C6H5, which is optionally substituted by halogen atom; SO2NR23R24, where R23 and R24 are each H or a lower alkyl group; the group <IMAGE> where R18 and R19 have the abovementioned meaning; the group CHR25OR26, where R25 is H or a lower alkyl group having up to 3 carbon atoms, and R26 is H, a lower alkyl group having up to 3 carbon atoms or the group <IMAGE> where R25 has the abovementioned meaning; the group C=CR27, where R27 is H, a lower alkyl group having up to 3 carbon atoms, an aralkyl group having up to 12 carbon atoms, CHR25R28, where R25 has the abovementioned meaning, and R28 is halogen, OR29, where R29 is H, a lower alkyl group having up to 3 carbon atoms or an oxygen-containing heterocyclic ring which contains 5 or 6 members, NR30R31, where R30 and R31 are H, or a lower alkyl group or together form a ring, or <IMAGE> where R18 and R19 have the abovementioned meaning; the group COOR32, where R32 is a lower alkyl group, and where each molecule can contain 2 or more identical or different RA groups; RC is H, a lower alkyl group or an alkoxy group, a cycloalkyl group having from 3 to 6 carbon atoms or an aralkyl group having up to 8 carbon atoms; the group (CH2)nOR33, where R33 is a lower alkyl group, a cycloalkyl group having from 3 to 6 carbon atoms or an aralkyl group having up to 8 carbon atoms, and n is an integer between 1 and 3, are prepared by a number of different processes. The compounds possess valuable pharmacological properties. They act, in particular, on the central nervous system and are suitable for use in psychopharmaceutical preparations.