Sphingosine 1-phosphate receptor 1 agonists: a patent review (2013-2015)

References

• Marsolais D, Rosen H. Chemical modulators of sphingosine-1-phosphate receptors as barrier-oriented therapeutic molecules. Nat Rev Drug Discov. 2009;8:297–307.
   PubMed Web of Science ®Google Scholar
• Rosen H, P J G-C, Sanna MG, et al. Sphingosine 1-phosphate receptor signaling. Annu Rev Biochem. 2009;78:743–768.
   PubMed Web of Science ®Google Scholar
• Rivera J, R L P, Olivera A. The alliance of sphingosine-1-phosphate and its receptors in immunity. Nat Rev Immunol. 2008;8:753–763.
   PubMed Web of Science ®Google Scholar
• Spiegel S, Milstien S. Sphingosine-1-phosphate: an enigmatic signalling lipid. Nat Rev Mol Cell Biol. 2003;4:397–407.
   PubMed Web of Science ®Google Scholar
• Clair T, Aoki J, Koh E, et al. Autotaxin hydrolyzes sphingosylphosphorylcholine to produce the regulator of migration, sphingosine-1-phosphate. Cancer Res. 2003;63:5446–5453.
   PubMed Web of Science ®Google Scholar
• Mendoza A, Bréart B, Ramos-Perez WR, et al. The transporter Spns2 is required for secretion of lymph but not plasma sphingosine-1-phosphate. Cell Rep. 2012;2:1104–1110.
   PubMed Web of Science ®Google Scholar
• Candelore MR, Wright MJ, Tota LM, et al. Phytosphingosine 1-phosphate: a high affinity ligand for the S1P4/Edg-6 receptor. Biochem Biophys Res Commun. 2002;297:600–606.
   PubMed Web of Science ®Google Scholar
• Cyster JG, Schwab SR. Sphingosine-1-phosphate and lymphocyte egress from lymphoid organs. Annu Rev Immunol. 2012;30:69–94.
   PubMed Web of Science ®Google Scholar
• Gonzalez-Cabrera PJ, Brown S, Studer SM, et al. S1P signaling: new therapies and opportunities. F1000Prime Rep. 2014;6:109.
   PubMedGoogle Scholar
• Liang J, Nagahashi M, Kim EY, et al. Sphingosine-1-phosphate links persistent STAT3 activation, chronic intestinal inflammation, and development of colitis-associated cancer. Cancer Cell. 2013;23:107–120.
   PubMed Web of Science ®Google Scholar
• Montrose DC, Scherl EJ, Bosworth BP, et al. Hla1 T. S1P1 localizes to the colonic vasculature in ulcerative colitis and maintains blood vessel integrity. J Lipid Res. 2013;54:843–851.
   PubMed Web of Science ®Google Scholar
• Teijaro JR, Walsh KB, Cahalan S, et al. Endothelial cells are central orchestrators of cytokine amplification during influenza virus infection. Cell. 2011;146:980–991.
   PubMed Web of Science ®Google Scholar
• Brinkmann V, Billich A, Baumruker T, et al. Fingolimod (FTY720): discovery and development of an oral drug to treat multiple sclerosis. Nat Rev Drug Discov. 2010;9:883–897.
   PubMed Web of Science ®Google Scholar
• Cohen JA, Chun J. Mechanisms of fingolimod’s efficacy and adverse effects in multiple sclerosis. Ann Neurol. 2011;69:759–777.
   PubMed Web of Science ®Google Scholar
• Park SI, Felipe CR, Machado PG, et al. Pharmacokinetic/pharmacodynamic relationships of FTY720 in kidney transplant recipients. Braz J Med Biol Res. 2005;38:683–694.
   PubMed Web of Science ®Google Scholar
• Shea BS, Brooks SF, Fontaine BA, et al. Prolonged exposure to sphingosine 1–phosphate receptor-1 agonists exacerbates vascular leak, fibrosis, and mortality after lung injury. Am J Respir Cell Mol Biol. 2010;43:662–673.
   PubMed Web of Science ®Google Scholar
• Kappos L, Radue EW, O’Connor P, et al. A placebo-controlled trial of oral fingolimod in relapsing multiple sclerosis. N Engl J Med. 2010;362:387–401.
   PubMed Web of Science ®Google Scholar
• Cohen JA, Barkhof F, Comi G, et al. Oral fingolimod or intramuscular interferon for relapsing multiple sclerosis. N Engl J Med. 2010;362:402–415.
   PubMed Web of Science ®Google Scholar
• Sanna MG, Liao J, Jo E, et al. Sphingosine 1-phosphate (S1P) receptor subtypes S1P1 and S1P3, respectively, regulate lymphocyte recirculation and heart rate. J Biol Chem. 2004;279:13839–13848.
   PubMed Web of Science ®Google Scholar
• Gergely P, Nuesslein-Hildesheim B, Guerini D, et al. The selective sphingosine 1-phosphate receptor modulator BAF312 redirects lymphocyte distribution and has species-specific effects on heart rate. Br J Pharmacol. 2012;167:1035–1047.
   PubMed Web of Science ®Google Scholar
• Pelletier D, Hafler DA. Fingolimod for multiple sclerosis. N Engl J Med. 2012;366:339–47.
   PubMed Web of Science ®Google Scholar
• Murakami A, Takasugi H, Ohnuma S, et al. Sphingosine 1-phosphate (S1P) regulates vascular contraction via S1P3 receptor: investigation based on a new S1P3 receptor antagonist. Mol Pharmacol. 2010;77:704–713.
   PubMed Web of Science ®Google Scholar
• Fryer RM, Muthukumarana A, Harrison PC, et al. The clinically-tested S1P receptor agonists, FTY720 and BAF312, demonstrate subtype-specific bradycardia (S1P₁) and hypertension (S1P₃) in rat. PLoS One. 2012;7:e52985.
   PubMed Web of Science ®Google Scholar
• Urbano M, Guerrero M, Rosen H, et al. Modulators of the Sphingosine 1-phosphate receptor 1. Bioorg Med Chem Lett. 2013;23:6377–6389.
   PubMed Web of Science ®Google Scholar
• Hanson MA, Roth CB, Jo E, et al. Crystal structure of a lipid G protein-coupled receptor. Science. 2012;335:851–5.
   PubMed Web of Science ®Google Scholar
• Actelion Pharmaceuticals Ltd. Pyridin-4-yl derivatives. WO014141171. 2014.
   Google Scholar
• Akaal Pharma Pty Ltd. Organic compounds. WO014063199 2014.
   Google Scholar
• Allergan Inc. 3-(4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenoxy)propan-2-ol Derivatives As Sphingosine-1 Phosphate Receptors Modulators. Wo013036530. 2013.
   Google Scholar
• Allergan Inc. Azetidine Derivatives As Sphingosine 1-phosphate (S1P) Receptor Modulators. US0140228341. 2014.
   Google Scholar
• Allergan Inc. Sulfinylbenzyl and thiobenzyl derivatives As Sphingosine 1-phosphate (S1P) Receptor Modulators. US0130217652. 2013.
   Google Scholar
• Allergan Inc. Azetidine derivatives as sphingosine-1 Phosphate receptors modulators. WO015026914. 2014.
   Google Scholar
• Allergan Inc. Alkyl Derivatives As Sphingosine-1 Phosphate Receptors Modulators. WO015026922. 2015.
   Google Scholar
• Allergan Inc. Phenoxy-azetidine Derivatives As Sphingosine-1-phosphate (S1P) Receptor Modulators. US0130217667. 2013.
   Google Scholar
• Allergan Inc. Phenoxy-azetidine Derivatives As Sphingosine 1-phosphate (S1P) Receptor Modulators. WO015085153. 2015.
   Google Scholar
• Allergan Inc. Phenoxy Derivatives As Sphingosine 1-phosphate (S1P) Receptor Modulators. US0130217651. 2013.
   Google Scholar
• Allergan Inc. Phenoxy Derivatives As Sphingosine 1-phosphate (S1P) Receptor Modulators. WO015085174. 2015.
   Google Scholar
• Allergan Inc. Disubstituted Phenoxy Azetidine Derivatives As Sphingosine-1-phosphate (S1P) Receptor Modulators. WO015073547. 2015.
   Google Scholar
• Allergan Inc. Disubstituted Phenoxy Derivatives As Sphingosine-1-phosphate (S1P) Receptor Modulators. WO015073556. 2015.
   Google Scholar
• Allergan Inc. Alkene Azetidine Derivatives As Sphingosine 1-phosphate (S1P) Receptor Modulators. US0140228344. 2014.
   Google Scholar
• Allergan Inc. Alkene Derivatives As Sphingosine 1-phosphate (S1P) Receptor Modulators. WO014124234. 2014.
   Google Scholar
• Allergan Inc. Allene Derivatives As Sphingosine 1-phosphate (S1P) Receptor Modulators. US0140135293. 2014.
   Google Scholar
• Allergan Inc. Disubstituted Aryl Azetidine Derivatives As Sphingosine-1-phosphate Receptors Modulators. WO015021109. 2015.
   Google Scholar
• Allergan Inc. Disubstituted Aryl Oxy Derivatives As Sphingosine-1- Phosphate Receptors Modulators. WO015021112. 2015.
   Google Scholar
• Allergan Inc. Novel Compounds As Receptor Modulators With Therapeutic Utility. US0130157982. 2013.
   Google Scholar
• Allergan Inc. Phosphonic Acid Compounds As Sphingosine-1-phosphate Receptor Modulators. US0140256945. 2014.
   Google Scholar
• Allergan Inc. Novel Aromatic Thio Compounds As Receptor Modulators. WO014093253. 2014.
   Google Scholar
• Allergan Inc. Bicyclic Derivatives As Sphingosine-1 -phosphate Receptors Modulators. WO015163936. 2015.
   Google Scholar
• Allergan Inc. Aryl Azetidine Derivatives As Sphingosine-1 Phosphate Receptors Modulators. WO015023839. 2015.
   Google Scholar
• Allergan Inc. Aryl Derivatives As Sphingosine-1 Phosphate Receptors Modulators. WO015023837. 2015.
   Google Scholar
• Allergan Inc. Amino Diol Derivatives As Sphingosine 1-phosphate (S1P) Receptor Modulators. US0140221498. 2014.
   Google Scholar
• Allergan Inc. Alkyne Derivatives As Sphingosine 1-phosphate (S1P) Receptor Modulators. US0140228445. 2014.
   Google Scholar
• Allergan Inc. Aryl Oxadiazole Derivatives As Sphingosine 1-phosphate (S1P) Receptor Modulators. US0140135366. 2014.
   Google Scholar
• Allergan Inc. 1, 2, 4-oxadiazoles Azetidine Derivatives As Sphingosine-1 Phosphate Receptors Modulators. WO014055921. 2014.
   Google Scholar
• Allergan Inc. Substituted Aryl-1,2,4-oxadiazole Derivatives Useful For The Treatment Of Interalia Ocular Or Inflammatory Diseases. WO014055916. 2014.
   Google Scholar
• Allergan Inc. Bicyclic 1, 2, 4-oxadiazoles Derivatives As Sphingosine-1 Phosphate Receptors Modulators. WO014055911. 2014.
   Google Scholar
• Allergan Inc. Aromatic Compounds Having Sphingosine-1-phosphonate (S1P) Receptor Activity. US0130018019. 2013.
   Google Scholar
• Allergan Inc. Substituted Diaryl Derivatives As Sphingosine Receptor Modulators. US0140235585. 2014.
   Google Scholar
• Allergan Inc. Substituted Diaryl Azetidine Derivatives As Sphingosine Receptor Modulators. US0140235613. 2014.
   Google Scholar
• Allergan Inc. Substituted Dihydropyrazoles As Sphingosine Receptor Modulators. US0140228324. 2014.
   Google Scholar
• Allergan Inc. Substituted Pyrazole Azetidines As Sphingosine Receptor Modulators. US0140228345. 2014.
   Google Scholar
• Allergan Inc. Substituted 4,5-dihydropyrazole-1,2,4-oxadiazole Derivatives As Sphingosine Receptor Modulators. Wo014127149. 2014.
   Google Scholar
• Allergan Inc. Substituted 1h-pyrazol-1,2,4-oxadiazole Derivatives As Sphingosine Receptor Modulators. Wo014127141. 2014.
   Google Scholar
• Allergan Inc. 2-thio-1,3,4-oxadiazoles Azetidine Derivatives As Sphingosine-1 Phosphate Receptors Modulators. US0140135365. 2014.
   Google Scholar
• Allergan Inc. 2-thio-1,3,4-oxadiazoles Derivatives As Sphingosine-1 Phosphate Receptors Modulators. US20140135291. 2014.
   Google Scholar
• Allergan Inc. Diphenyl Urea Derivatives As Formyl Peptide Receptor Modulators. WO2015108577. 2015.
   Google Scholar
• Allergan Inc. 1,3,4-alkenyl Oxadiazole Amino Acid Derivatives As Sphingosine-1-phosphate Receptors’ Modulators. WO015073140. 2015.
   Google Scholar
• Allergan Inc. 1,3,4-oxadiazoles-2-thio Azetidine Derivatives As Sphingosine-1 Phosphate Receptors Modulators. WO2014071355. 2014.
   Google Scholar
• Allergan Inc. 1,3,4-oxadiazoles-2-thio Derivatives As Sphingosine-1 Phosphate Receptors Modulators. WO014071342. 2014.
   Google Scholar
• Allergan Inc. Pyrazole Azetidine Derivatives As Sphingosine 1-phosphate (s1p) Receptor Modulators. WO014130927. 2014.
   Google Scholar
• Allergan Inc. Pyrazole Derivatives As Sphingosine 1-phosphate (S1P) Receptor Modulators. WO014130947. 2014.
   Google Scholar
• Allergan Inc. Substituted 6-methoxy-4-amino-n-phenyl-2-naphtamides As Sphingosine Receptor Modulators. US0140235592. 2014.
   Google Scholar
• Biogen Indec Ma Inc. S1p And/or Atx Modulating Agents. WO014081752. 2014.
   Google Scholar
• Biogen Indec Ma Inc. S1p And/or Atx Modulating Agents. WO014081756. 2014.
   Google Scholar
• Bristol-Myer Squibb, Bicyclic Compounds. US0140235591. 2014.
   Google Scholar
• Institute of Materia Medica, Chinese academy of medical science, Amino-propylene-glycol Derivatives, Preparation Method And Pharmaceutical Composition And Use Thereof. WO013004190. 2013.
   Google Scholar
• LG Life Science LTD. Sphingosine-1-phosphate Receptor Agonists, Methods Of Preparing The Same, And Pharmaceutical Compositions Containing The Same As An Active Agent. WO014129796. 2014.
   Google Scholar
• Richard D. Cadwell, Heterobicyclic Sphingosine 1-phosphate Analogs. US0140100195. 2014.
   Google Scholar
• SANOFI. Carboxylic Acid Derivatives Having An Oxazolo[4,5-c]pyridine Ring. US0130023558. 2013.
   Google Scholar
• SANOFI. Carboxylic Acid Derivatives Having An Oxazolo[5,4-b]pyridine Ring. US0130023557. 2013.
   Google Scholar
• SANOFI. Cycloalkyloxycarboxylic Acid Derivatives. US0130023545. 2013.
   Google Scholar
• SANOFI. Carboxylic Acid Derivatives Having An Oxazolo[5,4-d]pyrimidine Ring. Us0130023544. 2013.
   Google Scholar
• Suzhou Connect Biopharmaceuticals, LTD. Immune Adjustment Compound, Use Thereof And Pharmaceutical Composition Comprising Same. WO015039587 2015.
   Google Scholar
• The Regents of the University of California Azacyclic Constrained Analogs Of Fty720. WO015009731. 2015
   Google Scholar
• West-Faelische Wilhelms-Universitaet Muenster, New Ligands For Targeting Of S1p Receptors For In Vivo Imaging And Treatment Of Diseases. WO013026765. 2013.
   Google Scholar
• Briard E, Rudolph B, Desrayaud S, et al. MS565: A SPECT Tracer for Evaluating the Brain Penetration of BAF312 (Siponimod). ChemMedChem. 2015;10:1008–1018.
   PubMed Web of Science ®Google Scholar
• Gleeson MP. Generation of a set of simple, interpretable ADMET rules of thumb. J Med Chem. 2008;51:817–834.
   PubMed Web of Science ®Google Scholar
• Ghose AK, Herbertz T, Hudkins RL, et al. Knowledge-Based, Central Nervous System (CNS) Lead Selection and Lead Optimization for CNS Drug Discovery. ACS Chem Neurosci. 2012;3:50–68.
   PubMed Web of Science ®Google Scholar