.beta.-carbolines and their use as tranquilizers

A .beta.-carboline of the formula ##STR14## wherein R.sup.3 is OR.sup.I, wherein R.sup.I is C.sub.1-5 -alkyl, C.sub.3-7 -cycloalkyl or C.sub.7-10 -aralkyl;

• NR.sup.II R.sup.III, wherein R.sup.II is H and R.sup.III is C.sub.1-3 -acyl or C.sub.1-6 -alkoxycarbonyl, or R.sup.II and R.sup.III together with the connecting N-atom are pyrrolyl or piperidino;
• or
• SC.sub.1-5 -alkyl or SC.sub.7-10 -arylalkyl;
• R.sup.4 is H, C.sub.1-5 -alkyl or C.sub.1-5 -alkoxy-C.sub.1-5 -alkyl;
• R.sup.6 and R.sup.8 each independently is H, SO.sub.2 Cl, NO.sub.2, NR.sup.IV.sub.2 or SO.sub.2 NR.sup.IV.sub.2 wherein R.sup.IV is H, C.sub.1-5 -alkyl or allyl;
• and
• R.sup.5, R.sup.7 and R.sup.9 are H.

A pharmaceutical composition comprising a tranquilizing effective amount of a compound of the formula ##STR15## wherein R.sup.3 is halogen;

• OR.sup.I, wherein R.sup.I is H, C.sub.1-5 alkyl, C.sub.3-7 -cycloalkyl, C.sub.7-10 -aralkyl or C.sub.6-10 -aryl;
• NR.sup.II R.sup.III, wherein R.sup.II is H, C.sub.1-5 alkyl, C.sub.3-7 -cycloalkyl, C.sub.7-10 -aralkyl or C.sub.6-10 -aryl and R.sup.III is C.sub.1-5 alkyl, C.sub.1-3 -alkanoyl, C.sub.1-6 alkoxycarbonyl, carbamoyl, or R.sup.II and R.sup.III together with the connecting N-atom are pyrrolyl or piperidino;
• SO.sub.n R.sup.I, wherein n is 0, 1 or 2 and R.sup.I is as defined above;
• PO.sub.3 R.sup.IV R.sup.V, wherein R.sup.IV and R.sup.V each independently is H, C.sub.1-5 -alkyl, C.sub.3-7 -cycloalkyl, C.sub.7-10 -aralkyl or C.sub.6-10 aryl;
• or
• C.sub.3-7 -cycloalkyl, C.sub.8-12 -aralkenyl, or C.sub.6-10 -aryl, each of whose alkyl portion is optionally substituted by 1 to 3 of halogen, OR.sup.I, NR.sup.II R.sup.III, SO.sub.n R.sup.I, COOR.sup.I, CONR.sup.II R.sup.III, CSNR.sup.II R.sup.III, PO.sub.3 R.sup.IV R.sup.V, COR.sup.I or CN, wherein R.sup.I, R.sup.II, R.sup.III, R.sup.IV, R.sup.V and n are as defined above;
• R.sup.4 is H, C.sub.1-5 alkyl, C.sub.1-5 alkoxy-C.sub.1-5 -alkyl, COR.sup.VI or CSR.sup.VII, wherein R.sup.VI is H, C.sub.1-5 -alkyl-C.sub.3-7 -cycloalkyl, C.sub.7-10 -aralkyl, OH, O-C.sub.1-5 -alkyl, O-C.sub.3-7 -cycloalkyl, O-C.sub.7-10 -aralkyl or NR.sup.II R.sup.II, wherein R.sub.II is as defind above and the R.sup.II 's can be the same or different or both R.sup.II 's together with the N are pyrrolyl or piperidino and wherein R.sup.VII is H, C.sub.1-5 alkyl, C.sub.3-7 -cycloalkyl or C.sub.7-10 -aralkyl;
• R.sup.5 -R.sup.8 each independently is H, halogen, NO.sub.2, OR.sup.I, NR.sup.II R.sup.III, PO.sub.3 R.sup.IV R.sup.V, SO.sub.2 NR.sup.I R.sup.V, COOR.sup.I, CONR.sup.II R.sup.III, CSNR.sup.II R.sup.III and COR.sup.I wherein R.sup.I-V are as defined above and at most two of R.sup.5 -R.sup.8 can be non-H;
• and
• R.sup.9 is H, C.sub.1-5 alkyl, C.sub.1-3 -alkanoyl, carbamoyl, C.sub.1-6 -alkoxycarbonyl, or SO.sub.2 R.sup.VIII wherein R.sup.VIII is methyl or p-tolyl,
• and a pharmaceutically acceptable carrier.

A method of achieving a tranquilizing effect in a patient in need of such treatment comprising administering to the patient a tranquilizng effective amount of a compound of the formula ##STR16## wherein R.sup.3 is halogen;

• OR.sup.I, wherein R.sup.I is H, C.sub.1-5 alkyl, C.sub.3-7 -cycloalkyl, C.sub.7-10 -aralkyl or C.sub.6-10 -aryl;
• NR.sup.II R.sup.III, wherein R.sup.II is H, C.sub.1-5 alkyl, C.sub.3-7 -cycloalkyl, C.sub.7-10 -aralkyl or C.sub.6-10 -aryl and R.sup.III is C.sub.1-5 alkyl, C.sub.1-3 -alkanoyl, C.sub.1-6 alkoxycarbonyl, carbamoyl, or R.sup.II and R.sup.III together with the connecting N-atom are pyrrolyl or piperidino;
• SO.sub.n R.sup.I, wherein n is 0, 1 or 2 and R.sup.I is as defined above;
• PO.sub.3 R.sup.IV R.sup.V, wherein R.sup.IV and R.sup.V each independently is H, C.sub.1-5 -alkyl, C.sub.3-7 -cycloalkyl, C.sub.7-10 -aralkyl or C.sub.6-10 aryl;
• or
• C.sub.3-7 -cycloalkyl, C.sub.8-12 -aralkenyl, or C.sub.6-10 -aryl, each of whose alkyl portion is optionally substituted by 1 to 3 of halogen, OR.sup.I, NR.sup.II R.sup.III, SO.sub.n R.sup.I, COOR.sup.I, CONR.sup.II R.sup.III, CSNR.sup.II R.sup.III, PO.sub.3 R.sup.IV R.sup.V, COR.sup.I or CN, wherein R.sup.I, R.sup.II, R.sup.III, R.sup.IV, R.sup.V and n are as defined above;
• R.sup.4 is H, C.sub.1-5 alkyl, C.sub.1-5 alkoxy-C.sub.1-5 -alkyl, COR.sup.VI or CSR.sup.VII, wherein R.sup.VI is H, C.sub.1-5 -alkyl, C.sub.3-7 -cycloalkyl, C.sub.7-10 -aralkyl, OH, O-C.sub.1-5 -alkyl, O-C.sub.3-7 -cycloalkyl, O-C.sub.7-10 -aralkyl or NR.sup.II R.sup.II, wherein R.sub.II is as defined above and the R.sup.II 's can be the same or different or both R.sup.II 's together with the N are pyrrolyl or piperidino and wherein R.sup.VII is H, C.sub.1-5 alkyl, C.sub.3-7 -cycloalkyl or C.sub.7-10 -aralkyl;
• R.sup.5 -R.sup.8 each independently is H, halogen, NO.sub.2, OR.sup.I, NR.sup.II R.sup.III, PO.sub.3 R.sup.IV R.sup.V, SO.sub.2 NR.sup.I R.sup.V, COOR.sup.I, CONR.sup.II R.sup.III, CSNR.sup.II R.sup.III and COR.sup.I wherein R.sup.I-V are as defined above and at most two of R.sup.5 -R.sup.8 can be non-H;
• and
• R.sup.9 is H, C.sub.1-5 alkyl, C.sub.1-3 -alkanoyl, carbamoyl, C.sub.1-6 -alkoxycarbonyl, or SO.sub.2 R.sup.VIII wherein R.sup.VIII is methyl or p-tolyl.