A b-carboline derivative has the formula (Ia') or (Ia') wherein: X is -NH- or -CH=CH-; R2 is hydroxyl or alkoxy; R3 is H or alkyl; R8 is optionally substituted alkyl or aryl; R11 is O or S and R14 and R15 are independently hydrogen, alkyl, cycloalkyl, haloalkyl, perhaloalkyl, aryl, aralkyl, alkoxy, cycloalkoxy, mono or polyhaloalkoxy, aryloxy, aralkyloxy, hydroxyalkyl, alkyloxyalkyl, alkylthio, cycloalkylthio, mono or polyhaloalkylthio, arylthio, aralkylthio, formate, alkylcarbonyloxy, cycloalkoxycarbonyl, haloalkoxycarbonyl, aryloxycarbonyl, aralkyloxycarbonyl, dialkylaminoalkyl, dialkylamino, diarylamino, diaralkylamino, optionally substituted carboxamide, fornamide, alkylcarbonylamino, cycloalkylcarbonylamino, haloalkylcarbonylamino, perhaloalkylcarbonylamino, arylcarbonylamino, aralkylcarbonylamino, formyl, alkylcarbonyl, cycloalkylcarbonyl, haloalkylcarbonyl, perhaloalkylcarbonyl, arylcarbonyl, aralkylcarbonyl, carboxyl, alkoxycarbonyl, cycloalkoxycarbonyl, haloalkoxycarbonyl, aryloxycarbonyl, aralkyloxycarbonyl, alkylsulphonyl, cycloalkylsulphonyl, haloalkylsulphonyl, perhaloalkylsulphonyl, arylsulphonyl, aralkylsulphonyl, cyano or nitro radical. The compounds are useful for treating diseases associated with disorders of melatonin activity, depression, psychiatric disorders, sleeping disorders associated with traveling ('jet lag'), neurodegenerative diseases of the central nervous system and cancers.
Hypnotic beta-carboline derivatives as analogues of endogenous acetylated metabolites of melatonin