Patent CA-1317945-C (CA)
Title: Tricyclic pyridazopyridone derivatives
Inventor: FISCHER ULF
IPC: C07D495/14
Filed: 1986-11-21
Granted: 1993-05-18
Abstract: Abstract The compounds of the general formula                          I     wherein Ra signifies a phenyl,pyridyl or thienyl group optionally substituted by halogen, trifluoro-methyl, nitro, lower alkyl or lower alkoxy, Rb and Rc together with the carbon atom denoted by a signify a group of the formula >Ca-S-CH=CH- (a), >Ca-CH=CH-S- (b) or >Ca-CH=CH-CH=CH- (c) which is optionally substituted by halogen, trifluoromethyl, lower alkyl, lower alkoxy, nitro, amino or mono- or di(lower alkyl)amino and the dotted line signifies an additional bond, Rd signifies the group of the formula -(A1)m-(CO)n-(QlA2)q-Rl, m, n and q each signify the number 0 or 1, Al signifies lower alkylene, A2 signifies lower alkylene, a direct bond or the group -C0-, Ql signifies an oxygen atom or the group -NR2- R1 signifies hydlogen, hydroxy, cyano, nitro, halogen, lower alkoxy, lower alkyl, lower alkoxycarbonyl, aryl, a group of the formula -NR3X4 or a 5-membered saturated, partially unsaturated or aromatic heterocycle which is attached via a carbon atom and which is optionally substituted by one or two lower alkyl groups and optionally substituted by a (C3 (C3-6)-cycloalkl hydroxy, lower alkoxy, lower alkanoyloxy, lower hydroxyalkyl, lower alkoxyalkyl, lower alkanoyloxyalkyl, lower alkoxycarbonyl, lower alkanoyl, carbamoyl, mono- or di(lower alkyl)carbamoyl, oxo or alkylenedioxy group, R  signifies hydrogen, lower alkyl or aryl, R  and R4 each signifies hydrogen, lower alkyl, lower alkoxyalkyl, lower dialkoxyalkyl, lower alkylenedioxyalkyl, lower cyanoalkyl, lower haloalkyl, lower hydroxyalkyl, lower dihydroxyalkyl, lower alkanoyl, lower alkoxycarbonyl or a (C3-7)-cycloalkyl group which is optionally substituted by hydroxy, lower alkoxy, lower alkanoyl-oxy, lower hydroxyalkyl, lower alkoxyalkyl, lower alkanoyloxyalkyl, oxo, carbamoyl, mono- or di(lower alkyl)carbamoyl or by lower alkylenedioxy or R  and R4 together with the nitrogen atom signify a 3- to 7-membered saturated N-heterocycle which is optionally substituted by one or two lower alkyl groups and optionally substituted by one or two hydroxy, lower alkoxy, lower alkanoyloxy, lower hydroxyalkyl, lower alkoxyalkyl, lower alkanoyloxyalkyl, lower alkoxy-carbonyl, lower alkanoyl, carbamoyl, mono- or di(lower alkyl)carbamoyl, oxo or lower alkylenedioxy groups and which can contain as a ring member an oxygen or sulphur atom or the group >N-R5, and R5 signifies hydrogen, lower alkyl, lower hydroxyalkyl, lower alkoxyalkyl, lower alkanoyloxyalkyl, lower alkanoyl, lower alkoxycarbonyl, carbamoyl or mono- or ditlower alkyl)carbamoyl, with the proviso that n signifies the number O when q signifies the number 1 and A signifies the group -CO-O that R1 has a significance different from cyano, nitro, halogen or lower alkoxycarbonyl when q signifies the number O and n signifies the number l or when q signifies the number 1 and A2 signifies the group -CO-, and that R1 has a significance different from hydroxy, cyano, nitro, halogen, lower alkoxycarbonyl, lower alkoxy and -NR3R4 when q signifies the number 1 and A2 signifies a direct bond, and pharmaceutically acceptable acid addition salts of compounds of formula I which have one or more basic substituents have valuable pharmacological properties and can be used for the control or prevention of illnesses. In particular, they have muscle relaxant, sedative-hypnotic, anxiolytic and/or anticonvulsive activity and can accordingly be used in the control or prevention of muscle tensions, stress conditions, insomnia, anxiety states and/or convulsions.