Dihydropyrones with improved antiviral activity

Organic compounds -- part of the class 532-570 series – Organic compounds – Sulfonic acids or salts thereof

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544383, 5483235, 560 12, 556428, 558387, C07D30931

Patent

active

060463554

ABSTRACT:
This invention pertains to improved antiviral activity of 6,6-disubstituted-5,6-dihydropyran-2-ones caused by judicious placement of certain polar substituents at the 3 and/or 6 positions.
The same substituents which enhance the cellular activity also diminish cytotoxicity further enhancing the desirable properties of these agents as antivirals.

REFERENCES:
H. Skulnick et al., "Structure-Based Design of Nonpeptidic HIV Protease Inhibitors: The Sulfonamide-Substituted Cyclooctylpyranones" J. Med. Chem., 1997, 40:7, 1149-1164.
K. Romines et al., "Cycloalkylpyranones and Cycloalkylpyrones as HIV Protease Inhibitors: Exploring the Impact of Ring Size on Structure-Activity Relationships", J. Med. Chem., 1996, 39:20, 4125-4130.
S. Thaisrivongs et al., "Structure-Based Design of HIV Protease Inhibitors: 5,6-Dihydro-4-hydroxy-2-pyrones as Effective, Nonpeptidic Inhibitors", J. Med. Chem., 1996, 39:23, 4630-4642.
S. Thaisrivongs et al., "Structure-Based Design of HIV Protease Inhibitors: 5,6-Dihydro-4-hydroxy-2-pyrones as Non-Peptidic Inhibitors", J. Med. Chem., 1996, 39:22, 4349-4353.
T. Judge et al., "Asymmetric Syntheses and Absolute Stereochemistry of 5,6-Dihydro-.alpha.-pyrones, A New Class of Potent HIV Protease Inhibitors", J. Am. Chem. Soc., 1997, 119:15, 3627-3628.

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