Anthranilimide-based glycogen phosphorylase inhibitors for the treatment of type 2 diabetes: 1. Identification of 1-amino-1-cycloalkyl carboxylic acid headgroups

Bioorg Med Chem Lett. 2009 Feb 1;19(3):976-80. doi: 10.1016/j.bmcl.2008.11.085. Epub 2008 Nov 27.

Abstract

Optimization of the amino acid residue within a series of anthranilimide-based glycogen phosphorylase inhibitors is described. These studies culminated in the identification of anthranilimides 16 and 22 which displayed potent in vitro inhibition of GPa in addition to reduced inhibition of CYP2C9 and excellent pharmacokinetic properties.

MeSH terms

  • Animals
  • Aryl Hydrocarbon Hydroxylases / antagonists & inhibitors*
  • Aryl Hydrocarbon Hydroxylases / chemistry
  • Carboxylic Acids / chemistry*
  • Chemistry, Pharmaceutical / methods*
  • Crystallography, X-Ray
  • Cytochrome P-450 CYP2C9
  • Diabetes Mellitus, Type 2 / drug therapy*
  • Dogs
  • Drug Design
  • Glycine / chemistry
  • Glycogen Phosphorylase / antagonists & inhibitors*
  • Glycogen Phosphorylase / metabolism
  • Humans
  • Imides / chemistry
  • Imides / pharmacology*
  • Inhibitory Concentration 50
  • Liver / enzymology
  • Molecular Conformation
  • Rats
  • ortho-Aminobenzoates / chemistry
  • ortho-Aminobenzoates / pharmacology*

Substances

  • Carboxylic Acids
  • Imides
  • ortho-Aminobenzoates
  • CYP2C9 protein, human
  • Cytochrome P-450 CYP2C9
  • Aryl Hydrocarbon Hydroxylases
  • Glycogen Phosphorylase
  • Glycine