Process for preparing azacycloalkanoylaminothiazoles (LD 137e)

The present invention relates to new, efficient processes for the preparation of 5-(-2-oxyazolylalkylthio)-2-azacycloalkanoylaminothiazole compounds of formula I ##STR1##

or a pharmaceutically acceptable salt thereof, wherein:

R is alkyl, aryl or heteroaryl;

R¹, R², R³, R⁴ and R⁵ are each independently hydrogen, alkyl, aryl or heteroaryl;

R⁶ and R⁷ are each independently hydrogen, alkyl, aryl, heteroaryl, halogen, hydroxy or alkoxy;

R⁸ is hydrogen, alkyl, aryl, heteroaryl, CONR⁹, R¹⁰, COR¹¹ or COOR¹²;

R⁹, R¹⁰, R¹¹ and R¹² are each independently hydrogen, alkyl or aryl;

m equals 0 to 5; and

n equals 0 to 5,

which are novel, potent inhibitors of cyclin dependent kinases (cdks). The present invention further concerns new key intermediate compounds, a quaternary ammonium salt of formula III and a 2-oxazolylalkyl derivative of formula IX.