Patent EP-0054507-A2 (EP)
Inventor: NEEF GUNTER DR
IPC: A61P25/20
Filed: 1981-12-15
Abstract: 3-substituted beta-carbolines of the formula
     wherein
     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  is
         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 or
     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  is
     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.