Identification and Preclinical Pharmacology of ((1 R,3 S)-1-Amino-3-(( S)-6-(2-methoxyphenethyl)-5,6,7,8-tetrahydronaphthalen-2-yl)cyclopentyl)methanol (BMS-986166): A Differentiated Sphingosine-1-phosphate Receptor 1 (S1P1) Modulator Advanced into Clinical Trials

J Med Chem. 2019 Mar 14;62(5):2265-2285. doi: 10.1021/acs.jmedchem.8b01695. Epub 2019 Mar 6.

Abstract

Recently, our research group reported the identification of BMS-986104 (2) as a differentiated S1P1 receptor modulator. In comparison to fingolimod (1), a full agonist of S1P1 currently marketed for the treatment of relapse remitting multiple sclerosis (RRMS), 2 offers several potential advantages having demonstrated improved safety multiples in preclinical evaluations against undesired pulmonary and cardiovascular effects. In clinical trials, 2 was found to exhibit a pharmacokinetic half-life ( T1/2) longer than that of 1, as well as a reduced formation of the phosphate metabolite that is required for activity against S1P1. Herein, we describe our efforts to discover highly potent, partial agonists of S1P1 with a shorter T1/2 and increased in vivo phosphate metabolite formation. These efforts culminated in the discovery of BMS-986166 (14a), which was advanced to human clinical evaluation. The pharmacokinetic/pharmacodynamic (PK/PD) relationship as well as pulmonary and cardiovascular safety assessments are discussed. Furthermore, efficacy of 14a in multiple preclinical models of autoimmune diseases are presented.

MeSH terms

  • Animals
  • Bronchoalveolar Lavage Fluid
  • Clinical Trials as Topic*
  • Dose-Response Relationship, Drug
  • Half-Life
  • Humans
  • Naphthalenes / chemistry
  • Naphthalenes / pharmacokinetics
  • Naphthalenes / pharmacology*
  • Rats
  • Rats, Inbred Lew
  • Sphingosine-1-Phosphate Receptors / agonists*
  • Tetrahydronaphthalenes / chemistry
  • Tetrahydronaphthalenes / pharmacokinetics
  • Tetrahydronaphthalenes / pharmacology*

Substances

  • BMS-986166
  • Naphthalenes
  • Sphingosine-1-Phosphate Receptors
  • Tetrahydronaphthalenes