Nonpsychotropic biaryl cannabinoid agonists

MEDI 30

Karin Worm, kworm@adolor.com1, Q. Jean Zhou, jzhou@adolor.com1, Gabriel Stabley2, Robert N. DeHaven2, Nathalie C. Conway-James2, Christopher J LaBuda2, Michael Koblish2, Patrick J Little2, and Roland E. Dolle1. (1) Department of Chemistry, Adolor Corporation, 700 Pennsylvania Drive, Exton, PA 19341-1127, (2) Department of Pharmacology, Adolor Corporation, 700 Pennsylvania Drive, Exton, PA 19341-1127
Cannabinoid receptor agonists, such as CP55,940 and WIN 55,212-2, produce potent antinociception with equivalent efficacy to morphine in animal models of pain. They also induce a number of unwanted CNS side effects, which are accounted for by the central distribution pattern of CB1 receptors. Catalepsy in mice is indicative of CB1 activation and predictive of cannabinoid psychoactivity. A separation between therapeutic effects and undesirable CNS side effects could be accomplished by preventing the cannabinoid from crossing the blood brain barrier. We report here that it is possible to peripheralize CB ligands, using a unique combination of polar substituents on a cannabinomimetic biaryl core, retaining the binding affinity to the receptors but preventing CNS side effects from occurring as demonstrated by the absence of catalepsy in the ring test at doses up to 100 mg/kg i.p.. Synthesis, SAR and initial biological evaluation in animal models of pain will be presented.
 

Poster Session
7:00 PM-9:00 PM, Sunday, August 19, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Medicinal Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007