The design and synthesis of indazole and pyrazolopyridine based glucokinase activators for the treatment of type 2 diabetes mellitus

Bioorg Med Chem Lett. 2012 Dec 1;22(23):7100-5. doi: 10.1016/j.bmcl.2012.09.082. Epub 2012 Sep 29.

Abstract

Glucokinase activators represent a promising potential treatment for patients with Type 2 diabetes. Herein, we report the identification and optimization of a series of novel indazole and pyrazolopyridine based activators leading to the identification of 4-(6-(azetidine-1-carbonyl)-5-fluoropyridin-3-yloxy)-2-ethyl-N-(5-methylpyrazin-2-yl)-2H-indazole-6-carboxamide (42) as a potent activator with favorable preclinical pharmacokinetic properties and in vivo efficacy.

MeSH terms

  • Administration, Oral
  • Animals
  • Cell Line, Tumor
  • Diabetes Mellitus, Type 2 / drug therapy
  • Drug Design*
  • Glucokinase / chemistry*
  • Glucokinase / metabolism
  • Glucose Tolerance Test
  • Half-Life
  • Humans
  • Hypoglycemic Agents / chemical synthesis*
  • Hypoglycemic Agents / pharmacokinetics
  • Hypoglycemic Agents / therapeutic use
  • Indazoles / chemical synthesis
  • Indazoles / chemistry*
  • Indazoles / pharmacokinetics
  • Indazoles / therapeutic use
  • Insulin / metabolism
  • Kinetics
  • Protein Binding
  • Pyrazines / chemical synthesis*
  • Pyrazines / pharmacokinetics
  • Pyrazines / therapeutic use
  • Pyrazoles / chemistry*
  • Pyrazoles / pharmacokinetics
  • Pyrazoles / therapeutic use
  • Pyridines / chemistry*
  • Pyridines / pharmacokinetics
  • Pyridines / therapeutic use
  • Rats
  • Rats, Sprague-Dawley
  • Structure-Activity Relationship

Substances

  • 4-(6-(azetidine-1-carbonyl)-5-fluoropyridin-3-yloxy)-2-ethyl-N-(5-methylpyrazin-2-yl)-2H-indazole-6-carboxamide
  • Hypoglycemic Agents
  • Indazoles
  • Insulin
  • Pyrazines
  • Pyrazoles
  • Pyridines
  • pyrazolopyridine
  • Glucokinase