Smithkline Corporation

Blaine M Sutton

David T Hill

Ivan Lantos

Joseph Weinstock

James W Wilson

Charles E Berkoff

Donald T Walz

A new synthesis of auranofin comprising reacting 2,3,4,6-tetra-O-acetyl-.alpha.-D-glucopyranosyl bromide with a S-(triethylphosphineaurous)thiouronium salt.

Method for preparing auranofin

The S-gold salt of 2,3,4,6-tetra-O-acetyl-1-thio-.beta.-D-glucopyranose reacts with triethylphosphine in an organic solvent to produce auranofin.

Process and intermediate for preparing auranofin

A new synthesis of auranofin comprising reacting 2,3,4,6-tetra-O-acetyl-.alpha.-D-glucopyranosyl bromide with triethylphosphinegold(I) chloride and sodium or potassiumsulfide. Auranofin is an antiarthritic pharmaceutical compound. Auranofin is an orally active therapeutic agent which is useful in man as an antiarthritic.

Bis(triethylphosphine)gold salts are advantageous agents for preparing auranofin.

Auranofin is prepared by reacting 1-.beta.-D-thio-2,3,4,6-tetra-O-acetylglucose with a triethylphosphine gold mercaptide.

Process for preparing auranofin

Auranofin is prepared by direct O-acetylation of S-triethylphosphinegold 1-thio-.beta.-D-glucopyranoside.

Preparation of auranofin by O-acetylation

Auranofin and its congeners are prepared by the reaction of a S-substituted 2,3,4,6-tetra-O-acetyl-1-thio-.beta.-D-glucopyranose with a tertiary phosphine gold ester or sulfide.

Auranofin and its congeners are prepared by reacting a bis(polyacetylsaccharide)disulfide with a tertiary phosphinegold mercaptide in a suitable organic solvent.

1H-Pyrimido[5,4,3-kl]phenothiazine-1,3(2H)-diones are prepared from the corresponding 1-thione-3-one compounds by methylation followed by acid hydrolysis. The 1,3-dione products and 1-thione-3-one intermediates are useful as anti-arthritic agents.

Anti-arthritic 1H-pyrimido-(5,4,3-kl)phenothiazine-1,3(2H)-diones and

S-Heterocyclic derivatives of phosphine or phosphite gold mercaptides having anti-arthritic activity are disclosed.

Anti-arthritic compositions comprising s-heterocyclic derivatives of

Pharmaceutical compositions having anti-arthritic activity comprising an ester derivative of pulvinic acid and methods of producing anti-arthritic activity by administering internally said compositions. Certain of the pulvinic acid derivatives are novel compounds per se.

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Hatboro, PA, United States of America

Blaine M Sutton