CAS No 174484-41-4 , N-[3-[(1R)-1-[(2R)-4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3H-pyran-
5-yl]propyl]phenyl]-5-(trifluoromethyl)pyridine-2-sulfonamide

Title: Tipranavir
CAS Registry Number: 174484-41-4
CAS Name: N-[3-[(1R)-1-[(6R)-5,6-Dihydro-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-propyl-2H-pyran-3-yl]propyl]phenyl]-5-(trifluoromethyl)-2-pyridinesulfonamide
Synonyms: 5-trifluoromethyl-N-[3(R)-[1-[5,6-dihydro-4-hydroxy-2-oxo-6(R)-(2-phenethyl)-6(R)-n-propyl-2H-pyran-3-yl]propyl]phenyl]-2-pyridinesulfonamide
Manufacturers' Codes: PNU-140690
Trademarks: Aptivus (Boehringer, Ing.)
Molecular Formula: C31H33F3N2O5S
Molecular Weight: 602.66
Percent Composition: C 61.78%, H 5.52%, F 9.46%, N 4.65%, O 13.27%, S 5.32%
Literature References: Nonpeptidic HIV protease inhibitor (NPPI). Prepn: K. R. Romines et al., WO 9530670 (1995 to Upjohn); eidem, US 5852195 (1998 to Pharmacia & Upjohn); S. R. Turner et al., J. Med. Chem. 41, 3467 (1998); K. S. Fors et al., J. Org. Chem. 63, 7348 (1998). Antiviral activity: S. M. Poppe et al., Antimicrob. Agents Chemother. 41, 1058 (1997); vs multidrug resistant clinical isolates: B. A. Larder et al., AIDS 14, 1943 (2000). HPLC determn in plasma: E. Dailly et al., J. Chromatogr. B 832, 317 (2006). Clinical pharmacokinetics in combination with ritonavir: T. R. MacGregor et al., HIV Clin. Trials 5, 371 (2004). Clinical evaluation in HIV infection: S. McCallister et al., J. Acquir. Immune Defic. Syndr. 35, 376 (2004). Review of pharmacologic interactions with other HIV medications: M. Boffito et al., J. Clin. Pharmacol. 46, 130-139 (2006); of clinical development: B. Best, R. Haubrich, Expert Opin. Invest. Drugs 15, 59-70 (2006).
Properties: White solid from ethyl acetate + heptane, mp 86-89°. [a]D +20° (ethanol). Freely sol in dehydrated alcohol, propylene glycol. Insol in aq. buffer, pH 7.5.
Melting point: mp 86-89°
Optical Rotation: [a]D +20° (ethanol)
Therap-Cat: Antiviral.
Keywords: Antiviral; Protease Inhibitor.