Process for preparing optically active dihydropyrones

Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters

Reexamination Certificate

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Reexamination Certificate

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07041845

ABSTRACT:
The invention relates to a process for preparing optically active 5-hydroxy-3-ketoesters of formula A1 or A2,or one of the tautomers thereof,the use thereof for preparing optically active dihydropyrones of formula B,and the use of the dihydropyrones of formula B thus prepared as starting compounds for preparing pharmaceutically active compounds, particularly Tipranavir.

REFERENCES:
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patent: 10108471 (2002-11-01), None
patent: WO 9819997 (1998-05-01), None
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Francotte ER, Enantioselective chromatography as a powerful alternative for the preparation of drug enantiomers, J Chromatogr A. Jan. 12, 2001;906(1-2):379-97.
Web page located at http://www.raell.demon.co.uk/chem/CHIbook/Chiral.htm, 1999.
Practical HPLC method development, 2nd Edition, Synder, Lloyd R; Kirkland, J. J; Glajch, Joseph L.; New York : John Wiley & Sons, c1997, pp. 586-581.
S. Levin and S. Abu-Lafi, The Role of Enantioselective Liquid Chromatographic Separations Using Chiral Stationary Phases in Pharmaceutical Analysis, in Advances in Chromatography. E. Grushka and P. R. Brown, Eds., Marcel Dekker Inc.; NY. vol. 33, 1993: 233-266.
Steve R. Turner et al; Tipranavir (PNU-140690): A Potent, Orally Bioavailable Nonpeptidic HIV Protease Inhibitor of the 5,6-Dihydro-4-hydroxy-2-pyrone sulfonamide Class; J. Med. Chem. (1998) vol. 41 pp. 3467-3476; American Chemical Society.
Copy of International Search Report Reference #PCT/EP 03/13851.

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