Discovery of a potent, selective, and orally active human epidermal growth factor receptor-2 sheddase inhibitor for the treatment of cancer

J Med Chem. 2007 Feb 22;50(4):603-6. doi: 10.1021/jm061344o. Epub 2007 Jan 26.

Abstract

The design, synthesis, evaluation, and identification of a novel class of (6S,7S)-N-hydroxy-6-carboxamide-5-azaspiro[2.5]octane-7-carboxamides as the first potent and selective inhibitors of human epidermal growth factor receptor-2 (HER-2) sheddase is described. Several compounds were identified that possess excellent pharmacodynamic and pharmacokinetic properties and were shown to decrease tumor size, cleaved HER-2 extracellular domain plasma levels, and potentiate the effects of the humanized anti-HER-2 monoclonal antibody (trastuzumab) in vivo in a HER-2 overexpressing cancer murine xenograft model.

MeSH terms

  • Administration, Oral
  • Amides / chemical synthesis*
  • Amides / pharmacokinetics
  • Amides / pharmacology
  • Animals
  • Antibodies, Monoclonal / pharmacology
  • Antibodies, Monoclonal, Humanized
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacokinetics
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Drug Synergism
  • Humans
  • Hydroxamic Acids / chemical synthesis*
  • Hydroxamic Acids / pharmacokinetics
  • Hydroxamic Acids / pharmacology
  • Mice
  • Molecular Conformation
  • Piperidines / chemical synthesis*
  • Piperidines / chemistry
  • Piperidines / pharmacology
  • Receptor, ErbB-2 / antagonists & inhibitors*
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry
  • Spiro Compounds / pharmacology
  • Stereoisomerism
  • Structure-Activity Relationship
  • Transplantation, Heterologous
  • Trastuzumab

Substances

  • Amides
  • Antibodies, Monoclonal
  • Antibodies, Monoclonal, Humanized
  • Antineoplastic Agents
  • Hydroxamic Acids
  • INCB3619
  • Piperidines
  • Spiro Compounds
  • Receptor, ErbB-2
  • Trastuzumab