Synthesis and Biological Characterization of Aryl Uracil Inhibitors of Hepatitis C Virus NS5B Polymerase: Discovery of ABT-072, a trans-Stilbene Analog with Good Oral Bioavailability

J Med Chem. 2018 Feb 8;61(3):1153-1163. doi: 10.1021/acs.jmedchem.7b01630. Epub 2018 Jan 25.

Abstract

ABT-072 is a non-nucleoside HCV NS5B polymerase inhibitor that was discovered as part of a program to identify new direct-acting antivirals (DAAs) for the treatment of HCV infection. This compound was identified during a medicinal chemistry effort to improve on an original lead, inhibitor 1, which we described in a previous publication. Replacement of the amide linkage in 1 with a trans-olefin resulted in improved compound permeability and solubility and provided much better pharmacokinetic properties in preclinical species. Replacement of the dihydrouracil in 1 with an N-linked uracil provided better potency in the genotype 1 replicon assay. Results from phase 1 clinical studies supported once-daily oral dosing with ABT-072 in HCV infected patients. A phase 2 clinical study that combined ABT-072 with the HCV protease inhibitor ABT-450 provided a sustained virologic response at 24 weeks after dosing (SVR24) in 10 of 11 patients who received treatment.

MeSH terms

  • Administration, Oral
  • Biological Availability
  • Chemistry Techniques, Synthetic
  • Cytosine / analogs & derivatives*
  • Cytosine / chemical synthesis
  • Cytosine / chemistry
  • Cytosine / pharmacokinetics
  • Cytosine / pharmacology
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacokinetics
  • Enzyme Inhibitors / pharmacology*
  • Hepacivirus / enzymology*
  • Humans
  • Permeability
  • Stereoisomerism
  • Stilbenes / chemistry*
  • Sulfonamides / chemical synthesis*
  • Sulfonamides / chemistry
  • Sulfonamides / pharmacokinetics
  • Sulfonamides / pharmacology*
  • Tissue Distribution
  • Viral Nonstructural Proteins / antagonists & inhibitors*
  • Viral Nonstructural Proteins / chemistry

Substances

  • ABT-072
  • Enzyme Inhibitors
  • Stilbenes
  • Sulfonamides
  • Viral Nonstructural Proteins
  • Cytosine
  • NS-5 protein, hepatitis C virus