Impurities of tazarotene: isolation and structural characterisation

J Pharm Biomed Anal. 2008 Feb 13;46(3):574-6. doi: 10.1016/j.jpba.2007.11.004. Epub 2007 Nov 17.

Abstract

Two impurities showing structures 5 and 6 were isolated and characterised by means of NMR analysis, during the optimisation of a synthetic procedure to tazarotene. Impurity 5, i.e. ethyl 6-((4,4-dimethyl-4H-thiochromen-6-yl)ethynyl)nicotinate, was a by-product of the reduction of the intermediate sulfoxide 7 with PCl(3). Impurity 6, i.e. 1,4-bis(4,4-dimethylthiochroman-6-yl)buta-1,3-diyne, was due to a side reaction of the Sonogashira coupling.

MeSH terms

  • Drug Contamination*
  • Magnetic Resonance Spectroscopy
  • Nicotinic Acids / analysis*
  • Nicotinic Acids / chemical synthesis
  • Nicotinic Acids / chemistry

Substances

  • Nicotinic Acids
  • tazarotene