Fused thiazolyl alkynes as potent mGlu5 receptor positive allosteric modulators

Bioorg Med Chem Lett. 2013 Jul 15;23(14):4037-43. doi: 10.1016/j.bmcl.2013.05.070. Epub 2013 May 30.

Abstract

A new series of potent fused thiazole mGlu5 receptor positive allosteric modulators (PAMs) (10, 11 and 27-31) are disclosed and details of the SAR and optimization are described. Optimization of alkynyl thiazole 9 (Lu AF11205) led to the identification of potent fused thiazole analogs 10b, 27a, 28j and 31d. In general, substituted cycloalkyl, aryl and heteroaryl carboxamides, and carbamate analogs are mGlu5PAMs, whereas smaller alkyl carboxamide, sulfonamide and sulfamide analogs tend to be mGlu5 negative allosteric modulators (NAMs).

MeSH terms

  • Alkynes / chemistry*
  • Allosteric Regulation
  • Amides / chemical synthesis
  • Amides / chemistry
  • Amides / metabolism
  • Carbamates / chemical synthesis
  • Carbamates / chemistry
  • Carbamates / metabolism
  • Humans
  • Protein Binding
  • Receptor, Metabotropic Glutamate 5 / chemistry*
  • Receptor, Metabotropic Glutamate 5 / metabolism
  • Structure-Activity Relationship
  • Thiazoles / chemical synthesis
  • Thiazoles / chemistry*
  • Thiazoles / metabolism

Substances

  • Alkynes
  • Amides
  • Carbamates
  • Receptor, Metabotropic Glutamate 5
  • Thiazoles