Elarofiban is a novel, nonpeptide, orally active fibrinogen
receptor antagonist useful for the treatment of platelet mediated
thrombotic disorders (Costanzo, M. J.; Hoekstra, W. J.;
Maryanoff, B. E. WO, 97/41102, 1997). Herein we describe the
process research that was carried out for the synthesis of
elarofiban that eventually led to the development of a safe and
cost-effective commercial scale process.
Preparation of methyl (S)-3-amino-3-(3′-pyridyl)propionate dihydrochloride in high enantiomeric purity by selective crystallization of a diastereomeric salt of a carboxylic acid precursor (N-BOC-protected) with (1R,2S)-(-)-ephedrine is described. Further demonstration of the usefulness of this procedure to resolve other 3-amino-3-[(substituted)pyridyl]propionic acids is also described.
Several methods for the synthesis of bemarinone, 5,6‐dimethoxy‐4‐methyl‐2(1H)‐quinazolinone, were explored with the most successful being a directed metalation route. Details of the lithiation and the subsequent reaction with electrophiles of 3′,4′‐dimethoxy‐2,2‐dimethylpropioanilide and other derivatives of 3,4‐dimethoxyaniline are given.
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