RESUMEN

During the synthesis of ezetimibe, two process related impurities were detected were HPLC analysis at levels ranging from 0.05 to 0.8%. These two impurities were isolated by column chromatography and co-injected with ezetimibe sample to confirm the retention times in HPLC. These two impurities were characterized as 2-(4-hydroxybenzyl)-N,5-bis(4-fluorophenyl) pentanamide (impurity-I) and 1-(4-fluorophenyl)-3(3-(4-fluorophenyl)propyl)-4-(4-hydroxyphenyl)azetidin-2-one (impurity-II). Isolation, structural elucidation of these impurities by spectral data ((1)H NMR, (13)C NMR, MS and IR) and probable mechanism of their formation have been discussed.

Asunto(s)

Anticolesterolemiantes/química , Azetidinas/química , Acetonitrilos/química , Anticolesterolemiantes/análisis , Azetidinas/análisis , Química Farmacéutica , Colesterol/química , Cromatografía Líquida de Alta Presión , Cromatografía en Capa Delgada , Contaminación de Medicamentos , Ezetimiba , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Estructura Molecular , Ácidos Fosfóricos/química , Espectrofotometría Infrarroja , Espectroscopía Infrarroja por Transformada de Fourier , Tecnología Farmacéutica