Anadys Pharmaceuticals, Inc.

Hoffmann-la Roche Inc.

Gregory Jay Haley

Stephen Evan Webber

Binh Vu

Alan X Xiang

Erik J Rueden

Joseph R Lennox

Klaus B Simonsen

Nader Fotouhi

David J Kucera

Norman Kong

Emily Aijun Liu

Tingmin Wang

Fritz Blatter

Martin Viertelhaus

The invention relates to methods for making deoxyribofuranose compounds such as compound (2) which are useful intermediates in the preparation of pharmaceutical compounds such as 5-amino-3-(2'-O-acetyl-3&#x2032;-deoxy-&#x3b2;-D-ribofuranosyl)-3H-thiazolo[4,5-d]pyrimidin-2-one and the like. 

Method of preparing deoxyribofuranose compounds

The invention is directed to 3,5-disubstituted and 3,5,7-trisubstituted-3H-oxazolo and 3H-thiazolo[4,5-d]pyrimidin-2-one compounds and prodrugs thereof that have immunomodulatory activity. The invention is also directed to the therapeutic or prophylactic use of such compounds and pharmaceutical compositions containing them, and to methods of treating diseases and disorders described herein, by administering effective amounts of such compounds and prodrugs.

3,5-disubstituted and 3,5,7-trisubstituted-3H-oxazolo and 3H-thiazolo[4,5-d]pyrimidin-2-one compounds and prodrugs thereof

The present disclosure relates to methods for preparing furanose compounds of Formula (3), which are useful as intermediates in the preparation of a p-toluene sulfonic acid salt of 5-amino-3-(2'-O-acetyl-3&#x2032;-deoxy-beta-D-ribofuranosyl)-3H-thiazolo[4,5-d]pyrimidin-2-one and the like. 

Method for preparing furanose compounds

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and the pharmaceutically acceptable salts and esters thereof, wherein X, X, X, Y, Yand R are described herein inhibit the interaction of MDM2 protein with a p53-like peptide and hence have anti proliferative activity.

Chiral cis-imidazolines

The present disclosure relates to p-toluene sulfonic acid salt of 5-amino-3-(2'-O-acetyl-3&#x2032;-deoxy-beta-D-ribofuranosyl)-3H-thiazolo[4,5-d]pyrimidin-2-one and to its use in treating conditions such as viral infections, tumors, and cancer.  Also disclosed is a method of preparing the p-toluene sulfonic acid salt of 5-amino-3-(2&#x2032;-O-acetyl-3&#x2032;-deoxy-&#x3b2;-D-ribofuranosyl)-3H-thiazolo[4,5-d]pyrimidin-2-one and methods for producing furanose compounds which are useful intermediates in the preparation of pharmaceutical compounds such as p-toluene sulfonic acid salt of 5-amino-3-(2&#x2032;-O-acetyl-3&#x2032;-deoxy-&#x3b2;-D-ribofuranosyl)-3H-thiazolo[4,5-d]pyrimidin-2-one and the like.

P-toluene sulfonic acid salt of 5-amino-3-(2'-O-acetyl-3&#x2032;-deoxy-&#x3b2;-D-ribofuranosyl)-3H-thiazole[4,5-d]pyrimidine-2-one and methods for preparation

The present invention relates to compounds of the formula and the pharmaceutically acceptable salts and esters thereof, a process for their manufacture, medicaments containing them as well as the use of these compounds as pharmaceutically active agents. The compounds show antiproliferative activity and may be especially useful for the treatment of cancer.

CIS-imidazolines

The invention is directed to 5-amino-3-(3'-deoxy-&#x3b2;-D-ribofuranosyl)-thiazolo[4,5-d]pyrimidin-2,7-dione prodrugs, whose metabolized parent compound has immunomodulatory activity. The invention also relates to the therapeutic use of such prodrugs and pharmaceutical compositions thereof in treating disease states associated with abnormal cell growth, such as cancer.

There are provided compounds of the formula I wherein R, V, Vand Ring A are described herein. The compounds exhibit anticancer activity.

Cis-imidazolines

There are presented compounds of the formula or pharmaceutically acceptable salts thereof,wherein Y, Y, X, X, Xand R are as described in this application. These compounds are believed to inhibit MDM2-p53 interaction and as such the compounds will have anti-hyperproliferative cellular activity.

3,5-Disubsitituted and 3,5,7-trisubstituted-3H-oxazolo and 3H-thiazolo[4,5-d]pyrimidin-2-one compounds and prodrugs thereof

The invention is directed to carbonate and carbamate prodrugs of thiazolo[4,5-d]pyrimidine compounds, whose metabolized parent compound has immunomodulatory activity. The invention also relates to the therapeutic use of such prodrugs and pharmaceutical compositions thereof in treating disease states associated with abnormal cell growth, such as cancer.

The present invention provides compounds according to formula I having the designations provided herein, and pharmaceutically acceptable salts and esters thereof. These compounds inhibit the interaction of MDM2 protein with a p53-like peptide and have antiproliferative activity.

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San Diego, CA, United States of America

Gregory Jay Haley