Tetralin derivatives, their preparation and use

Claim 1

A process for the preparation of a tetralin derivative of the formula I where R 1 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or halogen, R 2 is hydrogen, C 1 -C 6 -alkyl or C 3 -C 6 - cycloalkyl, X is ―CH 2 ―CO― ―CH 2 ―CHOH, ―CH 2 ―C(R 4 )OH―, ―CH 2 ―C(OCOR 4 )H―, ―CH 2 ―C(R 4 ) (OCHOR 5 )―, -CHOH-CHOH-, ―CH(OCOR 4 )―CH(OCOR 4 )―, ―CH 2 ―CH(OR 4 )― or (where R 4 and R 5 are each C 1 -C 4 -alkyl) and R 3 is nitrile, C 2 -C 10 -ketal or -CH(R 7 ) (R 8 )- or -CO-R 9 , where R 7 is hydrogen or C 1 -C 3 -alkyl, R 8 is hydrogen, C 1 -C 3 -alkyl or ―OR 10 or ―NR 11 R 12 (where R 10 , R" and R 12 are each hydrogen, C 1 -C 4 -alkyl, C 2 -C 20 -alkanoyl or unsubstituted or substituted benzoyl, or R" and R 12 , together with the nitrogen atom to which they are bonded, form a heterocyclic radical) and R9 is hydrogen, halogen, C 1 -C 4 -alkyl, azido , imidazolyl, triazolyl or ―OR 13 or ―NR 14 R 15 ( where R 13 is hydrogen or C 1 -C 8 -alkyl or is C 2 -C 6 -alkyl which is substituted by one or more hydroxyl groups or a C 1 -C 4 - alkoxy group, or is unsubstituted or substituted aryl or aralkyl which is unsubstituted or substituted in the aryl moiety, and R 14 and R 15 are each hydrogen or C 1 -C 6 -alkyl or are each C 2 -C 6 -alkyl which is substituted by one or more hydroxyl groups or are each aryl or tetrazolyl, or R 14 and R 15 , together with the nitrogen atom to which they are bonded, form a heterocyclic ring system possessing 3 to 6 ring atoms), and, where relevant, its physiologically tolerated salts, wherein a carbonyl compound of the formula (II) where X, R 1 and R 2 have the meanings stated above is subjected to a Wittig-Homer reaction with a phosphorus compound of the formula (III) where R 16 is C 1 -C 3 -alkyl and R 17 is C 1 -G 2 -alkyl, carbo-C 1 -C B -alkoxy, nitrile or (C 1 -C 4 -alkoxy)methyl, and, if desired, the resulting compound is A) where R 3 is COR 9 - hydrolyzed with an ester of the formula I (where R 3 is carbo-C 1 -C 8 -alkoxy) and the resulting acid is, if desired, esterified, amidated, reduced or - where R 3 is nitrile - hydrolyzed to give carboxylic acid or an acid amide or reduced to give the aldehyde and, if desired, a) the alcohol thus obtained is esterified, etherified or oxidized to the corresponding aldehyde or b) the resulting amine is converted to its amide and the resulting compound is, if desired, converted into its physiologically tolerated salts.