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Novel pyridine derivatives as potent and selective CB2 cannabinoid receptor agonists.

Abstract
Replacement of the phenyl ring in our previous (morpholinomethyl)aniline carboxamide cannabinoid receptor ligands with a pyridine ring led to the discovery of a novel chemical series of CB2 ligands. Compound 3, that is, 2,2-dimethyl-N-(5-methyl-4-(morpholinomethyl)pyridin-2-yl)butanamide was identified as a potent and selective CB2 agonist exhibiting in vivo efficacy after oral administration in a rat model of neuropathic pain.
AuthorsGuo-Hua Chu, Christopher T Saeui, Karin Worm, Damian G Weaver, Allan J Goodman, Robert L Broadrup, Joel A Cassel, Robert N DeHaven, Christopher J LaBuda, Michael Koblish, Bernice Brogdon, Steve Smith, Bertrand Le Bourdonnec, Roland E Dolle
JournalBioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 19 Issue 20 Pg. 5931-5 (Oct 15 2009) ISSN: 1464-3405 [Electronic] England
PMID19736007 (Publication Type: Journal Article)
Chemical References
  • 2,2-dimethyl-N-(5-methyl-4-(morpholinomethyl)pyridin-2-yl)butanamide
  • Aminopyridines
  • Morpholines
  • Pyridines
  • Receptor, Cannabinoid, CB1
  • Receptor, Cannabinoid, CB2
Topics
  • Administration, Oral
  • Aminopyridines (chemical synthesis, chemistry, pharmacology)
  • Animals
  • Dogs
  • Humans
  • Male
  • Microsomes, Liver
  • Morpholines (chemical synthesis, chemistry, pharmacology)
  • Pain (drug therapy)
  • Protein Binding
  • Pyridines (chemical synthesis, chemistry, pharmacokinetics)
  • Rats
  • Rats, Sprague-Dawley
  • Receptor, Cannabinoid, CB1 (agonists, metabolism)
  • Receptor, Cannabinoid, CB2 (agonists, metabolism)
  • Structure-Activity Relationship

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