1450979-79-9

Upstream product

• 73874-95-0 (piperidin-4-yl)carbamic acid tert-butyl ester 
• 1408075-34-2 1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]-piperidin-4-amine 
• 79-22-1 methyl chloroformate 
• 1408075-33-1 tert-butyl N-{1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]piperidin-4-yl}carbamate 
• 686344-50-3 6-chloro-9-(4-chlorophenyl)-8-(2-chlorophenyl)-9H-purine 

Relevant academic research and scientific papers

PERIPHERALLY RESTRICTED DIPHENYL PURINE DERIVATIVES

The invention provides compounds capable of acting as antagonists at cannabanoid receptors according to the following formula: Such compounds may be used to treat conditions for which the cannabinoid receptor system has been implicated, such as obesity, liver disease, diabetes, pain, and inflammation.

Peripherally selective diphenyl purine antagonist of the CB1 Receptor

Antagonists of the CB1 receptor can be useful in the treatment of several important disorders. However, to date, the only clinically approved CB1 receptor antagonist, rimonabant, was withdrawn because of adverse central nervous system (CNS)-related side effects. Since rimonabant's withdrawal, several groups are pursuing peripherally selective CB1 antagonists. These compounds are expected to be devoid of undesirable CNS-related effects but maintain efficacy through antagonism of peripherally expressed CB1 receptors. Reported here are our latest results toward the development of a peripherally selective analog of the diphenyl purine CB1 antagonist otenabant 1. Compound 9 (N-{1-[8-(2-chlorophenyl) -9-(4-chlorophenyl)-9H-purin-6-yl]piperidin-4-yl}pentanamide) is a potent, orally absorbed antagonist of the CB1 receptor that is >50-fold selective for CB1 over CB2, highly selective for the periphery in a rodent model, and without efficacy in a series of in vivo assays designed to evaluate its ability to mitigate the central effects of Δ9-tetrahydrocannabinol through the CB1 receptor.