ES391496A1 - Fused ring indole derivatives and a process for the manufacture thereof - Google Patents

Abstract

Procedure for the preparation of indole derivatives of the general formula **(See formula)** in which n and r are, independently, 1 or 2; R1 is halogen, hydroxy, cyano, lower alkyl, lower alkoxy, lower alkylthio, trifluoromethyl, carboxyl, benzyloxy, carbo-lower alkoxy, nitro, amino, mono-lower alkylamino, dialkylamino lower, sulfamoyl, di-lower alkylsulfamoyl or difluoromethylsulfonyl and, when r is 2, R1 with an adjacent symbol R1 is also lower alkylenedioxyl; R2 is hydrogen, lower alkyl, aralkyl, or haloaralkyl; and R3 is (see formula) (where A is cyano, hydroxyl or lower alkoxy, Y is hydrogen or methyl and m is 0 to 7) (see formula) (where B is hydroxy, carboxyl, lower alkyl, lower alkoxy, amino, mono-lower alkoxy, mono-lower alkylamino-lower alkoxy, Y is hydrogen or methyl and p is 0 to 7) provided that when R2 is hydrogen, R1 is other than lower alkoxy, their enantiomers and the respective salts, characterized by reacting a compound of the general formula **(See formula)** in which r and R2 have the same meaning as before, while R1 has the same meaning as before and is also hydrogen, with a compound of the general formula **(See formula)** in which n has the same meaning as before and R3'' is (see formula) -A (where A is cyano, hydroxyl or lower alkoxy, Y is hydrogen or methyl and m is 0 to 7) or (see formula), (where B is hydroxyl, carboxyl, lower alkyl, lower alkoxy, amino, mono-lower alkylamino or di-lower alkylamino, Y is hydrogen or methyl and p is 0 to 7), if desired, in a compound thus obtained in which B is a hydroxy group, this group be converted to a group of amino-lower alkoxy, mono-lower alkylamino-lower alkoxy or di-lower alkylamino-lower alkoxy; if desired, in a compound of formula I in which A is a cyano group or B is an amino, mono- or di-lower alkylamino or lower alkoxy group, this group or the group become (see formula), respectively, in a carboxylic group, if desired, in a compound of formula I in which A is a cyano group, this group being converted into an acid amide group; if desired, in a compound of formula I in which B is an amine group, convert the group (see formula) in a cyano group; if desired, in a compound of formula I, in which B is a hydroxy group, esterify the group (see formula); if desired in a compound of formula I in which (R1) r is a nitro group, convert this group to an amine group and replace this amine group, if desired, lower alkyl is introduced into a compound of formula I in where R2 is hydrogen; if desired, in a compound of formula I in which (R1) r is benzyloxy, this group be converted to a hydroxy group; introducing halogen into a compound of formula I thus obtained in which (R1) r is hydrogen, and, if desired, the bases or acids thus obtained are converted into salts. (Machine-translation by Google Translate, not legally binding)