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
LEADER 01000naa a22002652 4500
001 NLM157595889
003 DE-627
005 20231223080519.0
007 tu
008 231223s2005 xx ||||| 00| ||eng c
028 5 2 |a pubmed24n0525.xml 
035 |a (DE-627)NLM157595889 
035 |a (NLM)16142832 
040 |a DE-627  |b ger  |c DE-627  |e rakwb 
041 |a eng 
100 1 |a Busacca, Carl A  |e verfasserin  |4 aut 
245 1 0 |a Structure elucidation and total synthesis of a unique group of trace impurities in Tipranavir drug product 
264 1 |c 2005 
336 |a Text  |b txt  |2 rdacontent 
337 |a ohne Hilfsmittel zu benutzen  |b n  |2 rdamedia 
338 |a Band  |b nc  |2 rdacarrier 
500 |a Date Completed 28.02.2006 
500 |a Date Revised 09.12.2020 
500 |a published: Print 
500 |a Citation Status MEDLINE 
520 |a Copyright (c) 2005 John Wiley & Sons, Ltd. 
520 |a 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 
650 4 |a Journal Article 
650 7 |a Alcohols  |2 NLM 
650 7 |a Pyridines  |2 NLM 
650 7 |a Pyrones  |2 NLM 
650 7 |a Sulfonamides  |2 NLM 
650 7 |a tipranavir  |2 NLM 
650 7 |a ZZT404XD09  |2 NLM 
700 1 |a Campbell, Scot  |e verfasserin  |4 aut 
700 1 |a Saha, Anjan  |e verfasserin  |4 aut 
700 1 |a Lorenz, Jon C  |e verfasserin  |4 aut 
700 1 |a Grozinger, Karl  |e verfasserin  |4 aut 
700 1 |a Jones, Paul-James  |e verfasserin  |4 aut 
700 1 |a Grinberg, Nelu  |e verfasserin  |4 aut 
700 1 |a Shen, Sherry  |e verfasserin  |4 aut 
700 1 |a Lee, Heewon  |e verfasserin  |4 aut 
700 1 |a Qiu, Fenghe  |e verfasserin  |4 aut 
700 1 |a Granger, Alice  |e verfasserin  |4 aut 
700 1 |a Yuabova, Zhanna  |e verfasserin  |4 aut 
700 1 |a Norwood, Dan  |e verfasserin  |4 aut 
700 1 |a Senanayake, Chris H  |e verfasserin  |4 aut 
773 0 8 |i Enthalten in  |t Magnetic resonance in chemistry : MRC  |d 1985  |g 43(2005), 12 vom: 19. Dez., Seite 1032-9  |w (DE-627)NLM098179667  |x 1097-458X  |7 nnns 
773 1 8 |g volume:43  |g year:2005  |g number:12  |g day:19  |g month:12  |g pages:1032-9 
912 |a GBV_USEFLAG_A 
912 |a SYSFLAG_A 
912 |a GBV_NLM 
912 |a GBV_ILN_350 
951 |a AR 
952 |d 43  |j 2005  |e 12  |b 19  |c 12  |h 1032-9