| abstract |
3-substituted beta-carbolines of the formulan whereinn R A is H, F, Cl, Br, I, N0 2 , CN, CH 3 , CF 3 , SCH 3 , NR 16 R 17 or NHCOR 16 , wherein R 16 and R 17 are the same or different and each is hydrogen or alkyl, alkenyl or alkynyl each of up to 6 C-atoms, aralkyl or cycloalkyl each of up to 10 C-atoms, all of which groups for R 16 and R 17 , except for H, can optionally be substituted by halogen, hydroxy, SH, SR 23 , COOR 23 , nitrilo, CONR 23 R 24 , CHOR 23 OR 24 or CHSR 23 SR 24 , wherein R 23 and R 24 are the same or different and each is hydrogen or a lower alkyl of up to 3 C-atoms, or wherein R 16 and R 17 together form a saturated or unsaturated 3-7 membered heterocyclic ring, optionally substituted with a lower alkyl group of up to 3 C-atoms, =S, =0, OR 23 , SR 23 or NR 23 R 24 , wherein a C-atom in the hetero ring may optionally be replaced by S, O or NR 23 ; wherein, throughout, R 23 is as defined above; or R A isn wherein R 23 and R 24 are the same or different and each is as defined above; or R A is CHR 33 -OR 39 , wherein R 33 and R 39 are the same or different and R 33 is hydrogen or lower alkyl of up to 3 C-atoms and R 39 is hydrogen, lower alkyl of up to 3 C-atoms orn or R A is OR 18 wherein R 18 is alkyl, aryl or aralkyl each of up to 12 C-atoms; or R A is C- CR35 , wherein R 35 is hydrogen, lower alkyl of up to 3 C-atoms, aryl of up to 12 C atoms, or CH R 33 R 30 , wherein R 33 is as defined above and R 30 is halogen, OR 40 or NR 41 R 42 , wherein R 40 is hydrogen, lower alkyl of up to 3 C-atoms, or C 4 or 5-alkylene thereby forming a 5- or 6-membered heterocyclic ring containing 0 and wherein R 41 and R 42 are the same or different and each is hydrogen or lower alkyl, or together are C 4 or 5-alkylene forming a ring with the N-atom, or R 35 isn wherein R 23 and R 24 are as defined above; or R A is COOR 2 , SR 2 or SO 2 R 2 , wherein R 2 is alkyl of up to 6 C atoms; or R A is SO 2 NR 21 R 22 wherein R 21 and R 22 each is H or lower alkyl, and wherein each compound may contain 1-4 identical or different non-H R A groups; R c is hydrogen, lower alkyl, alkoxyalkyl of up to 6 C-atoms, cycloalkyl of 3-6 C-atoms, aralkyl of up to 8 C-atoms, or (CH 2 ) n OR 20 wherein R 20 is alkyl of up to 6 C-atoms, cycloalkyl of 3-6 C-atoms or aralkyl of up to 8 C-atoms and n is an integer of 1 to 3; Y is oxygen, two hydrogen atoms or NOR 1 , wherein R 1 is hydrogen, lower alkyl, aryl or aralkyl of up to 6 C-atoms, COR 2 , wherein R 2 is lower alkyl of up to 6 C-atoms, or Y is CHCOOR 3 , wherein R 3 is hydrogen or lower alkyl or Y is NNR 4 R 5 , wherein R 4 and R 5 can be the same or different and each is hydrogen, lower alkyl, C 6-10 -aryl, C 7-10 -aralkyl or CONR 6 R 7 , wherein R 6 and R 7 can be the same or different and each is hydrogen or lower alkyl or R 4 and R 5 together with the connecting N-atom, for a 5- or 6-membered heterocyclic ring which optionally may also contain an 0-atom or up to 3 N-atoms and which optionally may be substituted by a lower alkyl group; Z is hydrogen, or alkoxy or aralkoxy each of up to 10 C-atoms and each optionally substituted by hydroxy, or Z is alkyl of up to 6 C-atoms, C 6-10 -aryl or C 7-10 -aralkyl each of which may optionally be substituted by a COOR 8 - or a CONR 9 R 10 group, wherein R 8 is alkyl of up to 6 C-atoms, and R 9 and R 10 , be the same or different and each is hydrogen or alkyl to 6 C-atoms; or Z is NR 9 R 10 , wherein R 9 and R 10 are as defined above; or Z is NR 11 CHR 12 R 13 , wherein R 11 and R 12 each is hydrogen or together form a N=C double bond, wherein R 13 is C 1-10 -alkyl or NR 14 R 15 , wherein R 14 and R 15 are the same or different and each is hydrogen, OH or alkyl or alkoxy each of up to 6 C-atoms, or wherein R 12 and R 13 together are oxygen, in which case, R" is hydrogen; or Z is COOR 2 wherein R 2 is as defined above; or Y and Z, together with the connecting C-atom, may form a 5- or 6-membered heterocyclic ring which contains an O-atom, adjoining 0- and N-atoms or up to 4 N atoms and which optionally may be substituted by a lower alkyl group, hydroxy or oxo have valuable psychotropic properties which make them useful for example as tranquilizers. |