Chromatographic resolution of closely related species in pharmaceutical chemistry: dehalogenation impurities and mixtures of halogen isomers

Analytical Chemistry
Erik L RegaladoChristopher J Welch

Abstract

In recent years, the use of halogen-containing molecules has proliferated in the pharmaceutical industry, where the incorporation of halogens, especially fluorine, has become vitally important for blocking metabolism and enhancing the biological activity of pharmaceuticals. The chromatographic separation of halogen-containing pharmaceuticals from associated isomers or dehalogenation impurities can sometimes be quite difficult. In an attempt to identify the best current tools available for addressing this important problem, a survey of the suitability of four chromatographic method development platforms (ultra high-performance liquid chromatography (UHPLC), core shell HPLC, achiral supercritical fluid chromatography (SFC) and chiral SFC) for separating closely related mixtures of halogen-containing pharmaceuticals and their dehalogenated isosteres is described. Of the 132 column and mobile phase combinations examined for each mixture, a small subset of conditions were found to afford the best overall performance, with a single UHPLC method (2.1 × 50 mm, 1.9 μm Hypersil Gold PFP, acetonitrile/methanol based aqueous eluents containing either phosphoric or perchloric acid with 150 mM sodium perchlorate) affording excellent separati...Continue Reading

References

Dec 6, 2003·Journal of Pharmaceutical and Biomedical Analysis·Sidika ErtürkSamiye Fiçicioğlu
Aug 8, 2009·Science·Ian W Davies, Christopher J Welch
Mar 10, 2010·Current Drug Targets·Marcelo Zaldini HernandesAna Cristina Lima Leite
Aug 27, 2010·Rapid Communications in Mass Spectrometry : RCM·Riet DamsDamiano Papini
Nov 14, 2012·Journal of Medicinal Chemistry·Rainer WilckenFrank M Boeckler
Aug 13, 2013·Journal of Fluorine Chemistry·Joshua SeitzIwao Ojima
Aug 16, 2013·Chirality·Wes SchaferChristopher J Welch
Sep 7, 2013·Science·Robert F Service
Sep 24, 2013·Journal of Chromatography. a·Erik L RegaladoChristopher J Welch

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Citations

Jan 29, 2014·Journal of Pharmaceutical and Biomedical Analysis·Erik L RegaladoChristopher J Welch
Jan 29, 2016·Journal of Chromatography. a·Stéphanie RomandDavy Guillarme
Dec 23, 2015·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·René Holm, David P Elder
Jan 22, 2015·Journal of Chromatography. a·Eric Lesellier, Caroline West
Jul 6, 2014·Journal of Separation Science·Christopher J Welch, Erik L Regalado
Sep 5, 2015·Physical Chemistry Chemical Physics : PCCP·Yoshiki NiihoriYuichi Negishi
Mar 7, 2014·Journal of Separation Science·Erik L RegaladoChristopher J Welch
Jun 16, 2015·Journal of Separation Science·Erik L Regalado, Christopher J Welch
Nov 23, 2016·Chemical Communications : Chem Comm·Chandan L BarhateErik L Regalado
Mar 5, 2014·Organic & Biomolecular Chemistry·Erik L RegaladoChristopher J Welch
Jan 26, 2021·Journal of the American Chemical Society·Mary E ZickPhillip J Milner
Mar 25, 2019·Journal of Pharmaceutical and Biomedical Analysis·Angéline NoireauCaroline West
Jan 27, 2015·Organic Letters·Teppei Fujimoto, Tobias Ritter
Jun 15, 2019·Accounts of Chemical Research·Erik L RegaladoDavy Guillarme
Feb 15, 2017·Analytical Chemistry·Chandan L BarhateChristopher J Welch

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