Discovery of diarylurea P2Y(1) antagonists with improved aqueous solubility

Bioorg Med Chem Lett. 2013 Jun 1;23(11):3239-43. doi: 10.1016/j.bmcl.2013.03.125. Epub 2013 Apr 6.

Abstract

Preclinical data suggests that P2Y1 antagonists, such as diarylurea compound 1, may provide antithrombotic efficacy similar to P2Y12 antagonists and may have the potential of providing reduced bleeding liabilities. This manuscript describes a series of diarylureas bearing solublizing amine side chains as potent P2Y1 antagonists. Among them, compounds 2l and 3h had improved aqueous solubility and maintained antiplatelet activity compared with compound 1. Compound 2l was moderately efficacious in both rat and rabbit thrombosis models and had a moderate prolongation of bleeding time in rats similar to that of compound 1.

MeSH terms

  • Animals
  • Caco-2 Cells
  • Disease Models, Animal
  • Drug Evaluation, Preclinical
  • Fibrinolytic Agents / chemical synthesis
  • Fibrinolytic Agents / chemistry*
  • Fibrinolytic Agents / pharmacokinetics
  • Half-Life
  • Humans
  • Microsomes, Liver / metabolism
  • Partial Thromboplastin Time
  • Phenylurea Compounds / chemistry*
  • Phenylurea Compounds / pharmacokinetics
  • Phenylurea Compounds / therapeutic use
  • Platelet Aggregation / drug effects
  • Purinergic P2Y Receptor Antagonists / chemistry*
  • Purinergic P2Y Receptor Antagonists / pharmacokinetics
  • Purinergic P2Y Receptor Antagonists / therapeutic use
  • Pyridines / chemistry*
  • Pyridines / pharmacokinetics
  • Pyridines / therapeutic use
  • Rabbits
  • Rats
  • Receptors, Purinergic P2Y1 / chemistry*
  • Receptors, Purinergic P2Y1 / metabolism
  • Solubility
  • Structure-Activity Relationship
  • Thrombosis / drug therapy
  • Urea / chemistry*
  • Urea / pharmacokinetics
  • Urea / therapeutic use
  • Water / chemistry

Substances

  • Fibrinolytic Agents
  • Phenylurea Compounds
  • Purinergic P2Y Receptor Antagonists
  • Pyridines
  • Receptors, Purinergic P2Y1
  • Water
  • Urea