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Synthesis of S-2-((S)-3-(4-chlorophenyl)-N'-((4-chlorophenyl)sulfonyl)-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboximidamido)-3-(methyl-d3 )butanamide-d5 , octadeuterated JD5037.

ABSTRACT: JD5037 (1) is a potent and selective, peripherally acting inverse agonist of the cannabinoid (CB1 R) receptor. Peripheral CB1 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 H8 ]-JD5037 (S, S) (8) along with its (S, R) diastereomer (13) from commercially available L-valine-d8 starting material. The [2 H8 ]-JD5037 compound will be used to quantitate unlabeled JD5037 during clinical ADME studies and will be used as an LC-MS/MS bioanalytical standard.

SUBMITTER: Iyer MR 

PROVIDER: S-EPMC5568925 | biostudies-literature | 2017 Aug

REPOSITORIES: biostudies-literature

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Synthesis of S-2-((S)-3-(4-chlorophenyl)-N'-((4-chlorophenyl)sulfonyl)-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboximidamido)-3-(methyl-d<sub>3</sub> )butanamide-d<sub>5</sub> , octadeuterated JD5037.

Iyer Malliga R MR   Cinar Resat R   Coffey Nathan J NJ   Chorvat Robert J RJ   Kunos George G  

Journal of labelled compounds & radiopharmaceuticals 20170802 10

JD5037 (1) is a potent and selective, peripherally acting inverse agonist of the cannabinoid (CB<sub>1</sub> R) receptor. Peripheral CB<sub>1</sub> 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 [<sup>2</sup> H<sub>8</sub> ]-JD5037 (S, S) (8) along with its (S, R) diastereomer (13) from commercially available L-valine-d<sub>8</sub> startin  ...[more]

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