Synthesis of S S ‐2‐(( S S )‐3‐(4‐chlorophenyl)‐ N N '‐((4‐chlorophenyl)sulfonyl)‐4‐phenyl‐4,5‐dihydro‐1 H H ‐pyrazole‐1‐carboximidamido)‐3‐(methyl‐ d d 3 3 )butanamide‐d 5 5 , octadeuterated JD5037

摘要

JD5037 ( 1 ) is a potent and selective, peripherally acting inverse agonist of the cannabinoid (CB 1 R) receptor. Peripheral CB 1 receptor antagonists/inverse agonists have great potential in the treatment of metabolic disorders like type 2 diabetes, obesity, and nonalcoholic steatohepatitis. We report the synthesis of octadeuterated [ 2 H 8 ]‐JD5037 ( S , S ) ( 8 ) along with its ( S , R ) diastereomer ( 13 ) from commercially available L ‐valine‐d 8 starting material. The [ 2 H 8 ]‐JD5037 compound will be used to quantitate unlabeled JD5037 during clinical ADME studies and will be used as an LC‐MS/MS bioanalytical standard.