Design, synthesis, and evaluation of indolinones as triple angiokinase inhibitors and the discovery of a highly specific 6-methoxycarbonyl-substituted indolinone (BIBF 1120)

J Med Chem. 2009 Jul 23;52(14):4466-80. doi: 10.1021/jm900431g.

Abstract

Inhibition of tumor angiogenesis through blockade of the vascular endothelial growth factor (VEGF) signaling pathway is a new treatment modality in oncology. Preclinical findings suggest that blockade of additional pro-angiogenic kinases, such as fibroblast and platelet-derived growth factor receptors (FGFR and PDGFR), may improve the efficacy of pharmacological cancer treatment. Indolinones substituted in position 6 were identified as selective inhibitors of VEGF-, PDGF-, and FGF-receptor kinases. In particular, 6-methoxycarbonyl-substituted indolinones showed a highly favorable selectivity profile. Optimization identified potent inhibitors of VEGF-related endothelial cell proliferation with additional efficacy on pericyctes and smooth muscle cells. In contrast, no direct inhibition of tumor cell proliferation was observed. Compounds 2 (BIBF 1000) and 3 (BIBF 1120) are orally available and display encouraging efficacy in in vivo tumor models while being well tolerated. The triple angiokinase inhibitor 3 is currently in phase III clinical trials for the treatment of nonsmall cell lung cancer.

MeSH terms

  • Administration, Oral
  • Animals
  • Carcinoma, Non-Small-Cell Lung / drug therapy
  • Cell Line, Tumor
  • Clinical Trials as Topic
  • Drug Discovery
  • Female
  • Humans
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Indoles / pharmacology*
  • Indoles / therapeutic use
  • Inhibitory Concentration 50
  • Lung Neoplasms / drug therapy
  • Mice
  • Protein Kinase Inhibitors / analogs & derivatives
  • Protein Kinase Inhibitors / chemical synthesis*
  • Protein Kinase Inhibitors / pharmacology*
  • Protein Kinase Inhibitors / therapeutic use
  • Receptors, Fibroblast Growth Factor / antagonists & inhibitors*
  • Receptors, Platelet-Derived Growth Factor / antagonists & inhibitors*
  • Substrate Specificity
  • Vascular Endothelial Growth Factor Receptor-2 / antagonists & inhibitors*

Substances

  • Indoles
  • Protein Kinase Inhibitors
  • Receptors, Fibroblast Growth Factor
  • Receptors, Platelet-Derived Growth Factor
  • Vascular Endothelial Growth Factor Receptor-2
  • nintedanib

Associated data

  • PDB/3C7Q