2′-Fluoronucleosides

US6348587B1 · kind B1 · utility

Assignees

• EMORY UNIVERSITY · US
• University of Georgia Research Foundation, Inc. · US

Inventors

• Raymond F. Schinazi · Decatur, US
• Dennis C. Liotta · Atlanta, US
• Chung K. Chu · Statham, US
• J. Jeffrey McAtee · Atlanta, US
• Junxing Shi · Duluth, US
• Yongseok Choi · Athens, US
• Kyeong Lee · Athens, US
• Joon H. Hong · Athens, US

Key dates

• Filing date: Feb 25, 1999
• Grant date: Feb 19, 2002
• Expiry date: Feb 25, 2019

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07H19/16
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

A class of 2′-fluoro-nucleoside compounds are disclosed which are useful in the treatment of hepatitis B infection, hepatitis C infection, HIV and abnormal cellular proliferation, including tumors and cancer. The compounds have the general formulae: whereinBase is a purine or pyrimidine base; R1 is OH, H, OR3, N3, CN, halogen, including F, or CF3, lower alkyl, amino, loweralkylamino, di(lower)alkylamino, or alkoxy, and base refers to a purine or pyrimidine base;R2 is H, phosphate, including monophosphate, diphosphate, triphosphate, or a stabilized phosphate prodrug; acyl, or other pharmaceutically acceptable leaving group which when administered in vivo, is capable of providing a compound wherein R2 is H or phosphate; sulfonate ester including alkyl or arylalkyl sulfonyl including methanesulfonyl, benzyl, wherein the phenyl group is optionally substituted with one or more substituents as described in the definition of aryl given above, a lipid, an amino acid, peptide, or cholesterol; andR3 is acyl, alkyl, phosphate, or other pharmaceutically acceptable leaving group which when administered in vivo, is capable of being cleaved to the parent compound, or a pharmaceutically acce…