Wisconsin Alumni Research Foundation

The Ohio State Research Foundation

The Ohio State University

University of California

Robert W Curley, Jr

Margaret Clagett-Dame

Hussein M Abou-Issa

Joel R Walker

Galal A Alshafie

Serena M Mershon

Michael D Collins

Victoria V Abzianidze

Michael J Panigot

Michael J Robarge

Jason S Chapman

Vishal Sikri

Linda A Tephly

Kevin L Weiss

Derek W Barnett

Compounds of the formula: are described, along with pharmaceutical compositions containing these compounds, and methods of using the compounds to prevent and to treat cancer in mammals, including humans.

C-linked glucuronide of N-(4-hydroxybenzyl) retinone, analogs thereof, and methods of using the same to inhibit neoplastic cell growth

C-linked glucuronide of N-(4-hydroxybenzyl) retinone, analogs thereof, and method of using the same to inhibit neoplastic cell growth

Analogs of 4-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-napthalenyl)-1-propenyl]benzoic acid and methods of manufacture and use thereof, such as for use in cancer prevention and treatment.

4-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-napthalenyl)-1-propenyl]benzoic acid analogs and method of manufacture and use thereof

A solid phase synthetic method for preparing arylretinamides is provided. The method comprises reacting hexachloroacetone with a solvent-suspended resin-bound triphenylphosphine to provide a suspension comprising an activated chlorinating reagent; reacting retinoic acid with the activated chlorinating reagent to provide retinoyl chloride; adding pyridine and a select arylamine to the resulting mixture; and stirring the resulting mixture for a time and at a temperature sufficient for the select arylamine to react with the retinoyl chloride and provide the arylretinamide. Also provided, are select arylretinamides that can be prepared by the present method, and methods of using such arylretinamides to induce apoptosis in cancer cells.

Solid phase synthesis of arylretinamides

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Disclosed are acid-stable compounds of Formula I: ##STR1## as well as pharmaceutical compositions containing the compounds as active ingredients, and methods to treat cancers in mammal, including humans, by administering one or more of the compounds to a subject in need thereof. The compounds are resistant to acid hydrolysis.

C-linked analogs of N-(4-hydroxyphenyl) retinamide

Novel acitretinamide compounds which are soluble and stable in water and useful in aqueous delivery systems, particularly to treat cancer, are provided. The novel acitretinamide compounds, 1-(D-glucopyranosyl)acitretinamide, 1-(D-glucopyranuronosyl)acitretinamide and the metal salts thereof, are hereinafter collectively referred to as the 'acitretinamide compounds'. The invention also relates to novel methods of making the acitretinamide compounds.

Stable acitretinoid compounds

The present invention provides breast cancer chemopreventive arylamide analogues of retinoic acid, more particularly C-glycoside analogues of N-(4-hydroxyphenyl)retinamide-O-glucuronide that resist both .beta.-glucuronidase mediated enzymatic hydrolysis as well as acid catalyzed hydrolysis. Specifically, the drugs include 4-(retinamido)phenyl-C-glucuronide; 4-(retinamido)phenyl-C-glucoside; 4-(retinamido)benzyl-C-xyloside; 4-(retinamido)benzyl-C-glucoside; 4-(retinamido)benzyl-C-glucuronide; and 4-(retinamido)phenyl-C-xyloside.

C-glycoside analogues of N-(4-hydroxyphenyl) retinamide-O-glucuronide

The present invention provides breast cancer chemopreventive arylamide analogues of retinoic acid, more particularly C-glycoside analogues of N-(4-hydroxyphenyl)retinamide-O-glucuronide and N-glycoside analogue of retinoyl .beta.-glucuronide that resist both .beta.-glucuronidase mediated enzymatic hydrolysis as well as acid catalyzed hydrolysis. Specifically, the drugs include 4-(retinamido)phenyl-C-glucuronide; 4-(retinamido)phenyl-C-glucoside; 4-(retinamido)benzyl-C-xyloside; 4-(retinamido)benzyl-C-glucoside; 4-(retinamido)benzyl-C-glucuronide; 4-(retinamido)phenyl-C-xyloside, 1-(B-D-glucopyranosyl) retinamide and 1-(D-glucopyranosyluronosly) retinamide. The invention also relates to a method for making such drugs.

C-glycoside analogues of N-(4-hydroxyphenyl)retinamide-O-glucuronide

Arylamide analogues of N-(4-hydroxyphenyl) retinamide-o-glucuronide

Growing community of inventors

Dublin, OH, United States of America

Robert W Curley, Jr