The syntheses of isotopically labelled CB-1 antagonists for the treatment of obesity

  • J Labelled Comp Radiopharm. 2016 Dec;59(14):665-672. doi: 10.1002/jlcr.3433.
Scott B Tran  1 ,  Brad D Maxwell  1 ,  Richard Burrell  2 ,  Samuel J Bonacorsi Jr  1
Affiliations
  • 1. Discovery Chemistry Platforms - Radiochemistry, Bristol-Myers Squibb, Inc, P.O. Box 4000, Princeton, NJ, 08543, USA.
  • 2. Discovery Chemistry Platforms - Radiochemistry, Bristol-Myers Squibb, Inc, P.O. Box 5100, Wallingford, CT, 06492, USA.
PMID: 27624665 DOI: 10.1002/jlcr.3433
Abstract

BMS-725519, BMS-811064, and BMS-812204 are potent and selective central Cannabinoid Receptor antagonists that have been investigated for the treatment of human obesity. To further understand their biotransformation profiles, radiolabelled and stable-labelled products were required. This paper describes the utility of [14 C]1,1-carbonyldiimidazole as a radiolabelling reagent for the syntheses of carbonyl-labelled [14 C]BMS-725519, [14 C]BMS-811064, and [14 C]BMS-812204. The syntheses of stable-labelled [13 C6 ]BMS-725519 and [13 CD313 CD2 ]BMS-812204 synthesized from of [13 C6 ]4-chloroacetophenone and [13 CD313 CD2 ]iodoethane, respectively, are also described.

Keywords
CB-1 antagonists; carbon-13; deuterium; synthesis.
Products