Discovery of MAP855, an Efficacious and Selective MEK1/2 Inhibitor with an ATP-Competitive Mode of Action

J Med Chem. 2022 Mar 10;65(5):4350-4366. doi: 10.1021/acs.jmedchem.1c02192. Epub 2022 Feb 23.

Abstract

Mutations in MEK1/2 have been described as a resistance mechanism to BRAF/MEK inhibitor treatment. We report the discovery of a novel ATP-competitive MEK1/2 inhibitor with efficacy in wildtype (WT) and mutant MEK12 models. Starting from a HTS hit, we obtained selective, cellularly active compounds that showed equipotent inhibition of WT MEK1/2 and a panel of MEK1/2 mutant cell lines. Using a structure-based approach, the optimization addressed the liabilities by systematic analysis of molecular matched pairs (MMPs) and ligand conformation. Addition of only three heavy atoms to early tool compound 6 removed Cyp3A4 liabilities and increased the cellular potency by 100-fold, while reducing log P by 5 units. Profiling of MAP855, compound 30, in pharmacokinetic-pharmacodynamic and efficacy studies in BRAF-mutant models showed comparable efficacy to clinical MEK1/2 inhibitors. Compound 30 is a novel highly potent and selective MEK1/2 kinase inhibitor with equipotent inhibition of WT and mutant MEK1/2, whose drug-like properties allow further investigation in the mutant MEK setting upon BRAF/MEK therapy.

MeSH terms

  • Adenosine Triphosphate / metabolism
  • Cell Line, Tumor
  • MAP Kinase Kinase 1
  • Mitogen-Activated Protein Kinase Kinases / metabolism
  • Mutation
  • Protein Kinase Inhibitors* / pharmacology
  • Protein Kinase Inhibitors* / therapeutic use
  • Proto-Oncogene Proteins B-raf* / genetics

Substances

  • Protein Kinase Inhibitors
  • Adenosine Triphosphate
  • Proto-Oncogene Proteins B-raf
  • MAP Kinase Kinase 1
  • Mitogen-Activated Protein Kinase Kinases