Discovery of Novel Selective and Orally Bioavailable Phosphodiesterase-1 Inhibitors for the Efficient Treatment of Idiopathic Pulmonary Fibrosis

J Med Chem. 2020 Jul 23;63(14):7867-7879. doi: 10.1021/acs.jmedchem.0c00711. Epub 2020 Jun 30.

Abstract

Idiopathic pulmonary fibrosis (IPF) is a chronic, progressive, and devastating lung disease lacking effective therapy. To identify whether phosphodiesterase-1 (PDE1) inhibition could act as a novel target for the treatment of IPF, hit-to-lead structural optimizations were performed on the PDE9/PDE1 dual inhibitor (R)-C33, leading to compound 3m with an IC50 of 2.9 nM against PDE1C, excellent selectivity across PDE subfamilies, reasonable drug-like properties, and remarkable pharmacodynamic effects as an anti-IPF agent. Oral administration of compound 3m (10 mg/kg) exerted more significant anti-pulmonary fibrosis effects than pirfenidone (150 mg/kg) in a bleomycin-induced IPF rat model and prevented transforming growth factor-β-induced fibroblast-to-myofibroblast conversion in vitro, indicating that PDE1 inhibition could serve as a novel target for the efficient treatment of IPF.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Bleomycin
  • Cell Differentiation / drug effects
  • Cyclic Nucleotide Phosphodiesterases, Type 1 / metabolism*
  • Drug Design
  • Humans
  • Idiopathic Pulmonary Fibrosis / chemically induced
  • Idiopathic Pulmonary Fibrosis / drug therapy*
  • Idiopathic Pulmonary Fibrosis / pathology
  • Lung / pathology
  • Male
  • Molecular Structure
  • Myofibroblasts / drug effects
  • Phosphodiesterase Inhibitors / chemical synthesis
  • Phosphodiesterase Inhibitors / metabolism
  • Phosphodiesterase Inhibitors / pharmacokinetics
  • Phosphodiesterase Inhibitors / therapeutic use*
  • Protein Binding
  • Pyrazoles / chemical synthesis
  • Pyrazoles / metabolism
  • Pyrazoles / pharmacokinetics
  • Pyrazoles / therapeutic use*
  • Pyrimidinones / chemical synthesis
  • Pyrimidinones / metabolism
  • Pyrimidinones / pharmacokinetics
  • Pyrimidinones / therapeutic use*
  • Rats, Sprague-Dawley
  • Structure-Activity Relationship
  • Thermodynamics

Substances

  • Phosphodiesterase Inhibitors
  • Pyrazoles
  • Pyrimidinones
  • Bleomycin
  • Cyclic Nucleotide Phosphodiesterases, Type 1