Synthesis and optimization of 4,5,6,7-tetrahydrooxazolo[4,5-c]pyridines as potent and orally-active metabotropic glutamate receptor 5 negative alloste...

Basic Information

ID: ALA4043199

Journal: Bioorg Med Chem Lett

Title: Synthesis and optimization of 4,5,6,7-tetrahydrooxazolo[4,5-c]pyridines as potent and orally-active metabotropic glutamate receptor 5 negative allosteric modulators.

Authors: Hirose W, Kato Y, Natsutani I, Takata M, Kitaichi M, Imai S, Hayashi S, Arai Y, Hoshino K, Yoshida K.

Abstract: We describe here the design, synthesis and characterization of a series of 4,5,6,7-tetrahydrooxazolo[4,5-c]pyridines as metabotropic glutamate receptor (mGluR) 5 negative allosteric modulators (NAMs). Optimization of the substituents led to the identification of several compounds with good pharmacokinetic profiles, including long half life and high oral bioavailability, in both rats and monkeys. The receptor occupancy test in the rat cortex revealed favorable brain penetration of these compounds. The reprsentative compound 13 produced oral antidepressant-like effect in the rat forced swimming test (MED: 0.3mg/kg, q.d.).

CiteXplore: 28838696

DOI: 10.1016/j.bmcl.2017.08.030

Patent ID: