Patent CA-1277659-C (CA)
Title: Tricyclic pyridine derivatives
Inventor: FISCHER ULF
IPC: C07D455/02
Filed: 1985-10-10
Granted: 1990-12-11
Abstract: Abstract The novel compounds of the general formula          I   wherein Ql and the nitrogen atom together signify a group of the formula >N-CH2CH2- (a), >N-CH2CH2CH2- (b), >N-C=CH- (c), >N-CH2-CH3CH- (d), >N-CH2-S(O)p- (e), >N-CH2CH2-S(O)p- (f) or >N-CH=CH-S(O)p- (g), P signifies the number 0, 1 or 2 and Ra signifies a phenyl, pyridyl or thienyl group which is optionally substituted by halogen, trifluoromethyl, nitro, lower alkyl or lower alkoxy, and either Rb and Rc each signify hydrogen, halogen, trifluoromethyl, lower alkyl, lower alkoxy or nitro and the dotted line signifies an optional bond, or Rb and Rc together with the carbon atom denoted by .alpha. signify a group of the formula >C.alpha.-S-CH=CH- (h), >C.alpha.-CH=CH-S- (i) or >Ca-CH=CH-CH=CH- (j) 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-(Q2A2)q-R1, m, n and q each signify the number 0 or 1, A1 signifies lower alkylene, A2 signifies lower alkylene, a direct bond or the group -CO-, Q2  signifies an oxygen atom or the group -NR2-, R1 signifies hydrogen, hydroxy, cyano, nitro, halogen, lower alkoxy, lower alkyl, lower alkoxycarbonyl, aryl, a group of the formula -NR3R4 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 (C3-6)-cycloalkyl, hydroxy, lower alkoxy, lower alkanoyloxy, lower hydroxyalkyl, lower alkoxyalkyl, lower alkanoyloxyalkyl, lower alkoxycar-bonyl, lower alkanoyl, carbamoyl, mono- or di(lower alkyl)carbamoyl, oxo or alkylenedioxy group, R2 signifies hydrogen, lower alkyl or aryl, R3 and R4 each signify 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 together with the nitrogen atom signify a 3- to 7-membered, saturated N-heterocycle which is optionally substi-tuted 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 alkoxycarbonyl, lower alkanoyl, carbamoyl, mono- or di(lower alkyl)car-bamoyl, 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 di(lower alkyl)carbamoyl, with the proviso that n signifies the number O when q signifies the number 1 and A2 signifies the group -CO-, that R1  has a significance different from cyano, nitro, halogen or lower alkoxycarbonyl when q signifies the number O and n signifies the number 1 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 valuabla pharmacological properties. In particular, they display pronounced muscle relaxant, seda-tive-hypnotic, anticonvulsive and/or anxiolytic properties and have only a low toxicity. They can be manufactured according to various methods which are known per se.