Novel sulfamoyl benzamides as selective CB2 agonists with improved in vitro metabolic stability

Ian Sellitto, Bertrand Le Bourdonnec, Karin Worm, Allan Goodman, Markku A. Savolainen, Guo Hua Chu, Christopher W. Ajello, Christopher T. Saeui, Lara K. Leister, Joel A. Cassel, Robert N. DeHaven, Christopher J. LaBuda, Michael Koblish, Patrick J. Little, Bernice L. Brogdon, Steven A. Smith, Roland E. Dolle

Research output: Contribution to journalArticle

11 Scopus citations

Abstract

A lead optimization campaign in our previously reported sulfamoyl benzamide class of CB2 agonists was conducted to improve the in vitro metabolic stability profile in this series while retaining high potency and selectivity for the CB2 receptor. From this study, compound 14, N-(3,4-dimethyl-5-(morpholinosulfonyl)phenyl)-2,2-dimethylbutanamide, was identified as a potent and selective CB2 agonist exhibiting moderate in vitro metabolic stability and oral bioavailability. Compound 14 demonstrated in vivo efficacy in a rat model of post-surgical pain.

Original languageEnglish
Pages (from-to)387-391
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume20
Issue number1
DOIs
StatePublished - Jan 1 2010
Externally publishedYes

Keywords

  • Agonists
  • Analgesics
  • CB

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    Sellitto, I., Bourdonnec, B. L., Worm, K., Goodman, A., Savolainen, M. A., Chu, G. H., Ajello, C. W., Saeui, C. T., Leister, L. K., Cassel, J. A., DeHaven, R. N., LaBuda, C. J., Koblish, M., Little, P. J., Brogdon, B. L., Smith, S. A., & Dolle, R. E. (2010). Novel sulfamoyl benzamides as selective CB2 agonists with improved in vitro metabolic stability. Bioorganic and Medicinal Chemistry Letters, 20(1), 387-391. https://doi.org/10.1016/j.bmcl.2009.10.062