Cyclic phosphoramidates as prodrugs of 2'-C-methylcytidine

Eur J Med Chem. 2009 Sep;44(9):3765-70. doi: 10.1016/j.ejmech.2009.04.043. Epub 2009 May 8.

Abstract

The currently approved treatment for hepatitis C virus infections is a combination of Ribavirin and pegylated Interferon. It leads to a sustained virologic response in approximately only half of the patients treated. For this reason there is an urgent need of new therapeutic agents. 2'-C-Methylcytidine is the first nucleoside inhibitor of the HCV NS5B polymerase that was efficacious in reducing the viral load in patients infected with HCV. The application of a monophosphate prodrug approach based on unprecedented cyclic phosphoramidates is reported. Our SAR studies led to compounds that are efficiently converted to the active triphosphate in human hepatocytes.

MeSH terms

  • Animals
  • Antiviral Agents / administration & dosage
  • Antiviral Agents / chemistry
  • Antiviral Agents / metabolism*
  • Antiviral Agents / pharmacology*
  • Cricetinae
  • Cytidine / administration & dosage
  • Cytidine / analogs & derivatives*
  • Cytidine / chemistry
  • Cytidine / metabolism
  • Cytidine / pharmacology
  • Drug Stability
  • Hepacivirus / drug effects*
  • Hepatitis C / drug therapy*
  • Hepatocytes / virology
  • Humans
  • Prodrugs / administration & dosage
  • Prodrugs / chemistry
  • Prodrugs / metabolism
  • Prodrugs / pharmacology*
  • Structure-Activity Relationship

Substances

  • Antiviral Agents
  • Prodrugs
  • 2'-C-methylcytidine
  • Cytidine