PREPARATION OF 4-(4-Methylsulfonylphenyl)-2-furanones USEFUL AS COX-2 INHIBITORS

A process for making compound of Formula I useful in the treatment of cyclooxygenase-2 mediated diseases comprises R 1 = C 1-6 alkyl, C 1-6 alkoxy, or optionally substituted phenyl or naphthyl radical R 2 and R 3 = independently represent C 1-6 alkyl, and optionally substituted by R 1 . (a) reacting...

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Bibliographic Details
Main Authors IOANNIS HOUPIS, ILIAS DORZIOTIS, KAN K ENG
Format Patent
LanguageEnglish
Published 05.05.1999
Edition6
Subjects
CHEMISTRY
HETEROCYCLIC COMPOUNDS
METALLURGY
ORGANIC CHEMISTRY
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Summary:A process for making compound of Formula I useful in the treatment of cyclooxygenase-2 mediated diseases comprises R 1 = C 1-6 alkyl, C 1-6 alkoxy, or optionally substituted phenyl or naphthyl radical R 2 and R 3 = independently represent C 1-6 alkyl, and optionally substituted by R 1 . (a) reacting a thioanisole of formula in a non-reactive solvent and in the presence of a Lewis Acid, with an acyl chloride to yield compound III (b) oxidizing compound III in a non-reactive solvent with an oxidizing agent, optionally in the presence of a suitable catalyst, to yield compound IV (c) reacting compound IV in an alkanol solvent with NBS and K 2 CO 3 to yield the epoxide compound of formula V (d)) reacting compound V in a non-reactive solvent with an alkyl or alkoxyacetic acid VI to yield a compound of formula VII and (e) reacting compound VII in an aprotic solvent with a strong base and dehydrating in the presence of a water scavenger to yield a compound of formula I
Bibliography:Application Number: GB19980023420