Beta-carboline-3-carboxylic acid derivs. - useful as psychotherapeutic agents, esp. tranquillisers and anticonvulsant (PT 10.2.81)

Beta-carboline derivs. of formula (I) are new: (where Q is CN or CXR3; X is O, S or NR10; R10 is H, 1-6C alkyl, 2-6C alkenyl or 3-7C cycloalkyl or cycloalkenyl. R3 is (a) a 1-10C alkoxy, 2-10C alkenyloxy, 6-10C anyloxy, 7-11C aralkoxy or 8-12C aralkenyloxy gp. opt. substd. by one or more OH, halogen, CF3, 1-10C alkoxy or 2-4C alkenyloxy gps. or by a NH2, di(1-6C alkyl)amino, 2-11C alkoxycarbonyl or 3-11C alkenyloxycarbonyl gp., or (b) NR11R12, where R11 and R12 are (i) H or OH, (ii) 1-10C alkyl, 2-10C alkenyl, 6-10C aryl, 7-11C aralkyl, 8-12C aralkenyl, 3-7C cycloalkyl or 3-7C cycloalkenyl gps. opt. substd. by OH, CONH2, COOH, 2-11C alkoxycarbonyl or 3-11C alkenyloxycarbonyl, or (iii) amino opt. substd. by 1-10C alkyl, 2-10C alkenyl, 6-10C aryl, 7-11C aralkyl, 8-12C aralkenyl, 3-7C cycloalkyl or 3-7C cycloalkenyl, or NR11R12 is a 5- to 7-membered heterocyclic ring opt. contg. another N or O atom and opt. substd. as in (ii), with the proviso that R11 and R12 are not both OH, that R11 and R12 are not both H when X is 0 and R4 is R is R9 is H, that one of R11 and R12 is not H when the other is NH2 and X is O and R4 is R is R9 is H, and that R4, R and R9 are not all H when X is O and R3 is MeO. R4 is H, 1-10C alkyl, 2-10C alkenyl, 3-7C cycloalkyl or cycloalkenyl, 7-10C aralkyl, 8-10C aralkenyl, phenyl, 7-10C alkoxyphenyl or 8-10C alkenyloxyphenyl. x is 1-4 and each R is independently F, Cl, Br, I, NO2, NR13R14, NHCOR13, CN, COOR13, OR13, SMe or SO2NR11R12, where R13 and R14 are H or 1-6C alkyl opt. substd. by OH or halogen. R9 is H, 1-8C alkyl, 2-8C alkenyl, 2-9C alkoxycarbonyl, 3-9C alkenyloxycarbonyl or 2-8C alkenyloxy).