Patent ID: 8263768

Claim:
A process for the stereoselective preparation of compounds of formula (I) optionally in the form of the tautomers thereof, and optionally the pharmacologically acceptable acid addition salts thereof, wherein R 1 denotes a group selected from among 3-chloro-2-fluoro-phenyl-amino, 3-chloro-4-fluoro-phenylamino, 2-fluoro-3-methyl-phenylamino, 2,5-difluoro-3-methyl-phenylamino, 3-chloro-2-methyl-phenylamino- and 2-fluoro-5-methyl-phenylamino, characterised in that the process comprises reaction steps (1 a ) to (1 d ), wherein (1 a ) is the reaction of a compound of formula (II) with a compound of formula (III) to form a compound of formula (IV) (1 b ) is the cleaving of the benzyl group of the compound of formula (IV) in the presence of a catalyst to form a compound of formula (V) (1 c ) is the reaction of the compound of formula (V) with a chlorinating agent to form the hydrochloride of a compound of formula (VI) and (1 d ) is the reaction of the compound of formula (VI) with one of the compounds (i) to (vi) to form a compound of formula (I), wherein (i) is 3-chloro-2-fluoro-aniline, (ii) is 3-chloro-4-fluoro-aniline, (ii) is 2-fluoro-3-methyl-aniline, (iii) is 2,5-difluoro-3-methyl-aniline, (iv) is 3-chloro-2-methyl-aniline, and (vi) is 2-fluoro-5-methyl-aniline, while steps (1 a ) to (1 d ) take place successively in the order specified, or characterised in that the process comprises reaction steps (2 a ), (1 c ) and (1 d ) wherein (2 a ) is the reaction of a compound of formula (II) with a compound of formula (VII) to form a compound of formula (V) while the steps take place successively in the order specified.