Substituted 3-(Pyridinylamino)-indoles and benzo[b]thiophenes, a process for their preparation and their use as medicaments

Claim 1

A process for the preparation of a compound of the formula I where R₁   is hydrogen, loweralkyl, loweralkenyl, loweralkynyl, arylloweralkyl, aminoloweralkyl, loweralkylaminoloweralkyl, formyl, loweralkylcarbonyl, aminoloweralkylcarbonyl or loweralkoxycarbonyl; the group -X-Y= is R₂ and R₃ being independently hydrogen or loweralkyl; W   is hydrogen, halogen, hydroxy, loweralkoxy, arylloweralkoxy or where R₄ is hydrogen, loweralkyl or arylloweralkyl; R₅ is loweralkyl or arylloweralkyl; or alternatively the group as a whole is , R₆ being hydrogen, loweralkyl, aryl or arylloweralkyl; and Z   is hydrogen, halogen, loweralkyl, nitro or amino; or a pharmaceutically acceptable acid addition salt thereof, which comprises a) reacting a compound of the formula V where Z is not NH₂, with a compound of the formulae or wherein R₂, R₃ and W are as defined, to form a compound of the formula I, wherein -X-Y=, W, Z and R₃ are as defined, and R₁ is hydrogen, b) optionally reacting a compound of the formula I, wherein -X-Y = is and R₃, W and Z are as defined, with a compound of the formula where R₇ is loweralkyl, to afford a compound of the formula I, where R₁ is the group where R₇ is loweralkyl, -X-Y = is and R₃, W and Z are as defined, c) optionally reacting a compound of the formula I as obtained in step b) above, with a loweralkyl halide of the formula R₂ Hal where R₂ is loweralkyl and Hal is chlorine or bromine or with a diloweralkylsulfate of the formula (R₂O)₂SO₂ to afford a compound of the formula I, wherein the group -X-Y = is where R₂ is loweralkyl, R₃, W and Z are as defined and R₁ is where R₇ is loweralkyl, d) optionally hydrolyzing a compound of the formula I as obtained in step c) above, to afford a compound of the formula I, wherein the group -X-Y = is where R₂ is loweralkyl, R₃, W and Z are as defined and R₁ is hydrogen, e) optionally reacting a compound of the formula I, wherein the group -X-Y = W, and R₃ are as defined, Z is as defined, but is not amino, R₂, if existent, is loweralkyl and R₁ is hydrogen, with a compound of the formula R₈-Hal, where R₈ is loweralkyl, loweralkenyl, loweralkynyl or arylloweralkyl and Hal is chlorine or bromine, to afford a compound of the formula I, wherein the group -X-Y=, W and R₃ are as defined, Z is as defined but is not amino, R₂, if existent, is loweralkyl and R₁ has the meaning of R₈ above, f) optionally reacting a compound of the formula I wherein -X-Y =, W and R₃ are as defined, Z is as defined but is not amino, R₂, if existent, is loweralkyl and R₁ is hydrogen, with a compound of the formula where Alk is a loweralkylene group and Hal is chlorine or bromine, to afford a compound of the formula I, wherein -X-Y =, W and R₃ are as defined, Z is as defined but is not amino, R₂, if existent, is loweralkyl and R₁ is the group and treating the compound obtained with hydrazine or methylamine to afford a compound of the formula I, where X-Y=, W and R₃ are as defined, Z is as defined but is not amino, R₂, if existent, is loweralkyl and R₁ is aminoloweralkyl, g) optionally reacting a compound of the formula I wherein -X-Y=, W and R₃ are as defined, Z is as defined but is not amino, R₂, if existent, is loweralkyl and R₁ is hydrogen, with a compound of the formula Hal-Alk-Hal wherein Alk is loweralkylene and Hal is chlorine or bromine, and reacting the product obtained with a compound of the formula R'NH₂, where R' is hydrogen or loweralkyl to afford a compound of the formula I, wherein -X-Y=, W and R₃ are as defined, Z is as defined but is not amino, R₂, if existent, is loweralkyl and R₁ is aminoloweralkyl or loweralkylaminoloweralkyl, h) optionally reacting a compound of the formula I, wherein -X-Y=, W and R₃ are as defined, Z is as defined but is not amino, R₂, if existent, is loweralkyl and R₁ is hydrogen, with a compound of the formula where R₉ is loweralkyl and Hal is chlorine or bromine, to afford a compound of the formula I, wherein -X-Y=, W and R₃ are as defined, Z is as defined, but is not amino, R₂, if existent, is loweralkyl and R₁ is loweralkylcarbonyl, i) optionally reacting a compound of the formula I, wherein -X-Y=, W and R₃ are as defined, Z is as defined but is not amino, R₂, if existent, is loweralkyl, and R₁ is hydrogen, with a compound of the formula where R is t-butyl or benzyl, Alk is loweralkylene and Hal is chlorine or bromine or with a compound of the formula where R and Alk are as defined, in the presence of dicyclohexylcarbodiimide, to afford a compound of the formula I, wherein R₁ is the group and subjecting the compound obtained to hydrolysis or catalytically hydrogenolysis to afford a compound of the formula I, wherein -X-Y=, W and R₃ are as defined, Z is as defined but is not amino, R₂, if existent, is loweralkyl and R₁ is aminoloweralkylcarbonyl, and j) optionally reducing a compound of the formula I, wherein -X-Y=, W and R₃ are as defined, Z is as defined but is not amino, R₂, if existent, is loweralkyl and R₁ is loweralkylcarbonyl, with a suitable reducing reagent to afford a compound of the formula I, wherein -X-Y=, W and R₃ are as defined, Z is as defined but is not amino, R₂, if existent, is loweralkyl and R₁ is loweralkyl.