Discovery of BAF312 (Siponimod), a Potent and Selective S1P Receptor Modulator

ACS Med Chem Lett. 2013 Jan 4;4(3):333-7. doi: 10.1021/ml300396r. eCollection 2013 Mar 14.

Abstract

A novel series of alkoxyimino derivatives as S1P1 agonists were discovered through de novo design using FTY720 as the chemical starting point. Extensive structure-activity relationship studies led to the discovery of (E)-1-(4-(1-(((4-cyclohexyl-3-(trifluoromethyl)benzyl)oxy)imino)ethyl)-2-ethylbenzyl)azetidine-3-carboxylic acid (32, BAF312, Siponimod), which has recently completed phase 2 clinical trials in patients with relapsing-remitting multiple sclerosis.

Keywords: S1P receptor; S1P1 agonist; lymphocytes.