Two non-racemic preparations of a piperidine-based NMDA antagonist with analgesic activity

Article abstract of DOI:10.1016/S0968-0896(97)00057-6

(2R,3S,1'R)-3-(1-Hydroxy-2-phosphonoethyl)-2-piperidinecarboxylic acid 1 has been synthesized by two different methods. The NMDA receptor binding affinities (K(i) values) are 74 nM for compound 1, and 64 nM for the corresponding ketone 2. The analgesic effects were evaluated using the mouse hot-plate test and the mouse formalin model. The ED₅₀ values for the racemates of compounds 1 and 2, using the mouse hotplate and intrathecal injection, were 0.53 and 0.51 nmol, respectively.