Patent CA-1188300-A (CA)
Inventor: NEEF GUENTER
IPC: A61K31/445
Filed: 1981-12-16
Granted: 1985-06-04
Abstract: ABSTRACT OF THE DISCLOSURE   3-substituted beta-carbolines of the formula   wherein RA   is  H, F, Cl, Br, l.  NO2, CN, CH3, CF3m SCG3,   NR16R17 or NHCOR16, R16 and R17 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 R16 and R17. except for H, can optionally be substituted by halogen, hydroxy, SH, SR23, COOR23, nitrilo. CONR23R24, CHOR23OR24 or CHSR23SR24, wherein R23 and R24 are the same or different and each is hydrogen or a lower alkyl of up to 3 C-atoms, or wherein R16 and R17 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, =O, OR23, SR23 or NR23R24, wherein a C-atom in the hetero ring may optionally be replaced by S, O or NR23; wherein, throughout, R23 is as defined above;   or RA is   wherein R23 and R24 are the same or different and each is as defined above; or RA is CHR33-OR39, wherein R33 and R39 are the same or different and R33 is hydrogen or lower alkyl of up to 3 C-atoms and R39 is hydrogen, lower alkyl of up to 3 C-atoms or   or RA is OR18 wherein R18 is alkyl, aryl or aralkyl each of up to 12 C-atoms; or RA is C ? CR35, wherein R35 is hydrogen, lower alkyl of up to 3 C-atoms, aryl of up to 12 C atoms, or CHR33R30, wherein R33 is as defined above and R30 is halogen, OR40 or NR41R42.         wherein R40 is hydrogen, lower alkyl or up to 3 C-atoms, or C4 or 5-alkylene thereby forming a 5- or 6-membered heterocyclic ring containing O and wherein R41 and R42 are the same or different and each is hydrogen or lower alkyl, or together are C4 or 5-alkylene forming a ring with the  N-atom, or R35 is   wherein R23 and R24 are as defined above;     or RA is COOR2, SR2 or SO2R2, wherein R2 is alkyl of up to 6 C atoms; or RA is SO2NR21R22 wherein R21 and R22 each is H or lower alkyl, and wherein each compound may contain 1-4 identical or different non-H RA groups; RC 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 (CH2)nOR20 wherein R20 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 NOR1, wherein R1 is hydrogen, lower alkyl, aryl or aralkyl of up to 6 C-atoms, COR2, wherein R2 is lower alkyl of up to 6 C-atoms, or Y is CHCOOR3, wherein R3 is hydrogen or lower alkyl or Y is NNR4R5, wherein R4 and R5 can be the same or different and each is hydrogen, lower alkyl, C6-10-aryl, C7-10-aralkyl or CONR6R7, wherein R6 and R7 can he the same or different and each is hydrogen or lower alkyl or R4 and R5 together with the connecting N-atom, for a 5- or 6-membered heterocyclic ring which optionally may also contain an O-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, C6-l0-aryl or C7-10-aralkyl each of which may optionally be substituted by a COOR8- or a CONR9R10 group.         wherein R8 is alkyl of up to 6 C-atoms. and R9 and R10 can be the same or different and each is hydrogen or alkyl of up to 6 C-atoms;     or Z is NR9R10, wherein R9 and R10 are as defined above; or Z is NR11CHR12R13, wherein R11 and R12 each is hydrogen or together form a N=C double bond, wherein R13 is C1-10-alkyl or NR14R15, wherein R14 and R15 are the same or different and each is hydrogen, OH or alkyl or alkoxy each of up to 6 C-atoms, or wherein R12 and R13 together are oxygen, in which case, R11 is hydrogen; or Z is COOR2 wherein R2 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 O- 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.