Process for the preparation of thiazole derivatives

Details Process for the preparation of thiazole derivatives Process for the preparation of thiazole derivatives

1999-08-13

2000-09-19

McKane, Joseph

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548205, C07D27720, C07D27728

Patent

active

061214558

DESCRIPTION:

BRIEF SUMMARY
The invention relates to a process for the preparation of a compound of the formula ##STR3## and, where applicable, its E/Z-isomers, mixtures of E/Z-isomers and/or tautomers, in each case in free form or in salt form, wherein unsubstituted or R.sub.4 -substituted C.sub.1 -C.sub.8 alkyl, or together form an alkylene bridge having two or three carbon atoms, and said alkylene bridge may additionally contain a hetero atom selected from the group consisting of NR.sub.5, O and S, alkyl, ##STR4## and, where applicable, its E/Z-isomers, mixtures of E/Z-isomers and/or tautomers, in each case in free form or in salt form, which is known or can be prepared by processes known per se and wherein substituted C.sub.2 -C.sub.4 alkenyl, unsubstituted or substituted C.sub.2 -C.sub.4 alkynyl, unsubstituted or substituted C.sub.3 -C.sub.6 cycloalkyl, unsubstituted or substituted aryl, unsubstituted or substituted heterocyclyl, or --SR.sub.6 ; and unsubstituted or substituted C.sub.2 -C.sub.4 alkenyl, unsubstituted or substituted C.sub.2 -C.sub.4 alkynyl, unsubstituted or substituted C.sub.3 -C.sub.6 cycloalkyl, unsubstituted or substituted aryl or unsubstituted or substituted heterocycyl, of the formula ##STR5## or, where applicable, an E/Z-isomer, a mixture of E/Z-isomers and/or a tautomer thereof, wherein into a compound of the formula ##STR6## or, where applicable, an E/Z-isomer, a mixture of E/Z-isomers and/or a tautomer thereof, wherein R, X and X.sub.1 are as defined above for formulae (II) and (III); optionally of a base, preferably in the presence of a base, into a compound of formula (III); formula ##STR7## or, where applicable, an E/Z-isomer, a mixture of E/Z-isomers and/or a tautomer thereof, in each case in free form or in salt form, which is known or can be prepared by processes known per se and wherein R.sub.1, R.sub.2, Y, Z and Q are as defined above for the compound of formula (I), into a compound of the formula ##STR8## or, where applicable, an E/Z-isomer, a mixture of E/Z-isomers and/or a tautomer thereof, in each case in free form or in salt form, which is known or can be prepared by processes known per se and wherein R.sub.1, R.sub.2, Y, Z and Q are as defined above for the compound of formula (I) and R is as defined above for the compound of formula (II); or formula (V) into a compound of formula (VI); and into a compound of formula (I); obtainable in accordance with the process or by another method, or an E/Z-isomer or tautomer thereof, in each case in free form or in salt form, into a different compound of formula (I) or an E/Z-isomer or tautomer thereof, in each case in free form or in salt form, separating a mixture of E/Z-isomers obtainable in accordance with the process and isolating the desired isomer, and/or converting a free compound of formula (I) obtainable in accordance with the process or by another method, or an E/Z-isomer or tautomer thereof, into a salt or converting a salt, obtainable in accordance with the process or by another method, of a compound of formula (I) or of an E/Z-isomer or tautomer thereof into the free compound of formula (I) or an E/Z-isomer or tautomer thereof or into a different salt.
Methods of synthesis for the compounds of formula (I) are described in the literature. It has been found, however, that the intermediates that have to be used in those synthesis processes known in the literature cause considerable problems during production on account of their high level of toxicity and, moreover, can be removed quantitatively from the active substance only with a significant outlay. Accordingly, the known processes are not satisfactory in that respect, giving rise to the need to make available improved preparation processes for those compounds.
Some compounds of formulae (I), (II), (III), (IV), (V) and (VI) contain asymmetric carbon atoms, as a result of which the compounds may occur in optically active form. Formulae (I) to (VI) are intended to include all those possible isomeric forms as well as mixtures thereof, for example racemates or mixtures of E/Z-isomers.
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