Structure elucidation and total synthesis of a unique group of trace impurities in Tipranavir drug product

Structure elucidation and total synthesis of a unique group of trace impurities in Tipranavir drug product

Copyright (c) 2005 John Wiley & Sons, Ltd.

Bibliographische Detailangaben
Veröffentlicht in:Magnetic resonance in chemistry : MRC. - 1985. - 43(2005), 12 vom: 19. Dez., Seite 1032-9
1. Verfasser: Busacca, Carl A (VerfasserIn)
Weitere Verfasser: Campbell, Scot, Saha, Anjan, Lorenz, Jon C, Grozinger, Karl, Jones, Paul-James, Grinberg, Nelu, Shen, Sherry, Lee, Heewon, Qiu, Fenghe, Granger, Alice, Yuabova, Zhanna, Norwood, Dan, Senanayake, Chris H
Format: Aufsatz
Sprache:English
Veröffentlicht: 2005
Zugriff auf das übergeordnete Werk:Magnetic resonance in chemistry : MRC
Schlagworte:Journal Article Alcohols Pyridines Pyrones Sulfonamides tipranavir ZZT404XD09
Beschreibung
Zusammenfassung:Copyright (c) 2005 John Wiley & Sons, Ltd.
Four unknown trace impurities (7-10) were observed in the capsule formulation of the HIV drug Tipranavir after prolonged storage at 30 degrees C/70% RH. Extensive NMR and LC/MS analyses revealed the compounds to be covalent adducts between TRIS, an excipient of the formulation, and diastereomeric Tipranavir alcohols formed via slow air oxidation of the drug substance. The structures were ultimately confirmed by total synthesis with final purification by chiral, preparative supercritical fluid chromatography. A novel Favorskii rearrangement to furnish butyrolactones was also uncovered during the synthesis
Beschreibung:Date Completed 28.02.2006
Date Revised 09.12.2020
published: Print
Citation Status MEDLINE
ISSN:1097-458X