Literature DB >> 24900288

Discovery of AMG 369, a Thiazolo[5,4-b]pyridine Agonist of S1P1 and S1P5.

Victor J Cee1, Mike Frohn1, Brian A Lanman1, Jennifer Golden1, Kristine Muller1, Susana Neira1, Alex Pickrell1, Heather Arnett2, Janet Buys1, Anu Gore1, Mike Fiorino1, Michelle Horner1, Andrea Itano1, Matt R Lee1, Michele McElvain1, Scot Middleton1, Michael Schrag1, Dalia Rivenzon-Segal3, Hugo M Vargas1, Han Xu1, Yang Xu1, Xuxia Zhang1, Jerry Siu1, Min Wong1, Roland W Bürli1.   

Abstract

The optimization of a series of thiazolopyridine S1P1 agonists with limited activity at the S1P3 receptor is reported. These efforts resulted in the discovery of 1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo-[5,4-b]pyridin-2-yl)benzyl)azetidine-3-carboxylic acid (5d, AMG 369), a potent dual S1P1/S1P5 agonist with limited activity at S1P3 and no activity at S1P2/S1P4. Dosed orally at 0.1 mg/kg, 5d is shown to reduce blood lymphocyte counts 24 h postdose and delay the onset and reduce the severity of experimental autoimmune encephalomyelitis in rat.

Entities:  

Keywords:  S1P1; Sphingosine-1-phosphate receptor; inflammation; lymphocyte; multiple sclerosis

Year:  2010        PMID： 24900288      PMCID： PMC4018127          DOI： 10.1021/ml100306h

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  20 in total

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Journal:  Science       Date:  2002-03-28       Impact factor: 47.728

Review 2.  Understanding pathogenesis and therapy of multiple sclerosis via animal models: 70 years of merits and culprits in experimental autoimmune encephalomyelitis research.

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4.  Physiochemical drug properties associated with in vivo toxicological outcomes.

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Journal:  Bioorg Med Chem Lett       Date:  2008-07-24       Impact factor: 2.823

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Journal:  N Engl J Med       Date:  2010-01-20       Impact factor: 91.245

7.  Sphingosine 1-phosphate (S1P) receptor subtypes S1P1 and S1P3, respectively, regulate lymphocyte recirculation and heart rate.

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Journal:  J Biol Chem       Date:  2004-01-19       Impact factor: 5.157

Review 8.  FTY720 (fingolimod) in Multiple Sclerosis: therapeutic effects in the immune and the central nervous system.

Authors:  Volker Brinkmann
Journal:  Br J Pharmacol       Date:  2009-10-08       Impact factor: 8.739

Review 9.  Metabolism and biological functions of two phosphorylated sphingolipids, sphingosine 1-phosphate and ceramide 1-phosphate.

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Journal:  Prog Lipid Res       Date:  2007-03-14       Impact factor: 16.195

Review 10.  Chemical modulators of sphingosine-1-phosphate receptors as barrier-oriented therapeutic molecules.

Authors:  David Marsolais; Hugh Rosen
Journal:  Nat Rev Drug Discov       Date:  2009-03-20       Impact factor: 84.694
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Review 1.  Modulators of the Sphingosine 1-phosphate receptor 1.

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Journal:  Bioorg Med Chem Lett       Date:  2013-09-29       Impact factor: 2.823

2.  Optimization of a Potent, Orally Active S1P1 Agonist Containing a Quinolinone Core.

Authors:  Paul E Harrington; Michael D Croghan; Christopher Fotsch; Mike Frohn; Brian A Lanman; Lewis D Pennington; Alexander J Pickrell; Anthony B Reed; Kelvin K C Sham; Andrew Tasker; Heather A Arnett; Michael Fiorino; Matthew R Lee; Michele McElvain; Henry G Morrison; Han Xu; Yang Xu; Xuxia Zhang; Min Wong; Victor J Cee
Journal:  ACS Med Chem Lett       Date:  2011-11-23       Impact factor: 4.345

3.  4-Methoxy-N-[2-(trifluoromethyl)biphenyl-4-ylcarbamoyl]nicotinamide: A Potent and Selective Agonist of S1P1.

Authors:  Lewis D Pennington; Kelvin K C Sham; Alexander J Pickrell; Paul E Harrington; Michael J Frohn; Brian A Lanman; Anthony B Reed; Michael D Croghan; Matthew R Lee; Han Xu; Michele McElvain; Yang Xu; Xuxia Zhang; Michael Fiorino; Michelle Horner; Henry G Morrison; Heather A Arnett; Christopher Fotsch; Min Wong; Victor J Cee
Journal:  ACS Med Chem Lett       Date:  2011-07-29       Impact factor: 4.345

Review 4.  Integrating the puzzle pieces: the current atomistic picture of phospholipid-G protein coupled receptor interactions.

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5.  Identification of Novel Thiazolo[5,4-b]Pyridine Derivatives as Potent Phosphoinositide 3-Kinase Inhibitors.

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Journal:  Molecules       Date:  2020-10-12       Impact factor: 4.411
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