Progress Toward JAK1-Selective Inhibitors

References

• Manning G , PlowmanGD, HunterT, SudarsanamS. Evolution of protein kinase signaling from yeast to man. Trends Biochem. Sci.27 (10), 514–520 (2002).
   PubMed Web of Science ®Google Scholar
• Knapp S , ArrudaP, BlaggJet al. A public-private partnership to unlock the untargeted kinome. Nat. Chem. Biol.9 (1), 3–6 (2013).
   PubMed Web of Science ®Google Scholar
• Cohen P , AlessiDR. Kinase drug discovery‐‐what's next in the field?ACS Chem. Biol.8 (1), 96–104 (2013).
   PubMed Web of Science ®Google Scholar
• Groom CR , HopkinsAL. Protein kinase drugs‐‐optimism doesn't wait on facts. Drug Discov. Today7 (15), 801–802 (2002).
   PubMed Web of Science ®Google Scholar
• Müller S , KnappS. Targeting kinases for the treatment of inflammatory diseases. Expert Opin. Drug Discov.5 (9), 867–881 (2010).
   PubMed Web of Science ®Google Scholar
• Fabian MA , BiggsWH3rd, TreiberDKet al. A small molecule-kinase interaction map for clinical kinase inhibitors. Nat. Biotechnol.23 (3), 329–336 (2005).
   PubMed Web of Science ®Google Scholar
• Karaman MW , HerrgardS, TreiberDKet al. A quantitative analysis of kinase inhibitor selectivity. Nat. Biotechnol.26 (1), 127–132 (2008).
   PubMed Web of Science ®Google Scholar
• Kurdi M , BoozGW. JAK redux: a second look at the regulation and role of JAKs in the heart. Am. J. Physiol. Heart Circ. Physiol.297 (5), H1545–H1556 (2009).
   PubMed Web of Science ®Google Scholar
• Menet, Christel J, Van Rompaey, Luc, Geney, Raphael. Advances in the discovery of selective JAK inhibitors. Prog. Med. Chem.52, 153–223 (2013).
   PubMedGoogle Scholar
• O'shea JJ , PesuM, BorieDC, ChangelianPS. A new modality for immunosuppression: targeting the JAK/STAT pathway. Nat. Rev. Drug Discov.3 (7), 555–564 (2004).
   PubMed Web of Science ®Google Scholar
• A study to evaluate both the efficacy and safetyprofile of CP-690,550 in patients with moderately to severely active ulcerative colitis (OCTAVE). https://clinicaltrials.gov/ct2/show/NCT01458951.
   Google Scholar
• Levy DE , LoomisCA. STAT3 signaling and the hyper-IgE syndrome. N. Engl. J. Med.357 (16), 1655–1658 (2007).
   PubMed Web of Science ®Google Scholar
• Sohn SJ , BarrettK, Van AbbemaAet al. A restricted role for TYK2 catalytic activity in human cytokine responses revealed by novel TYK2-selective inhibitors. J. Immunol. Baltim. Md 1950.191 (5), 2205–2216 (2013).
   Google Scholar
• Ishizaki M , MuromotoR, AkimotoTet al. Tyk2 is a therapeutic target for psoriasis-like skin inflammation. Int. Immunol.26 (5), 257–267 (2013).
   PubMed Web of Science ®Google Scholar
• Rodig SJ , MerazMA, WhiteJMet al. Disruption of the Jak1 gene demonstrates obligatory and nonredundant roles of the Jaks in cytokine-induced biologic responses. Cell93 (3), 373–383 (1998).
   PubMed Web of Science ®Google Scholar
• Haan C , RolveringC, RaulfFet al. Jak1 has a dominant role over Jak3 in signal transduction through γc-containing cytokine receptors. Chem. Biol.18 (3), 314–323 (2011).
   PubMedGoogle Scholar
• Ghoreschi K , LaurenceA, O'sheaJJ. Selectivity and therapeutic inhibition of kinases: to be or not to be?Nat. Immunol.10 (4), 356–360 (2009).
   PubMed Web of Science ®Google Scholar
• Flex E , PetrangeliV, StellaLet al. Somatically acquired JAK1 mutations in adult acute lymphoblastic leukemia. J. Exp. Med.205 (4), 751–758 (2008).
   PubMed Web of Science ®Google Scholar
• Meeting Materials, Arthritis Advisory Committee (2012). www.fda.gov/AdvisoryCommittees/CommitteesMeetingMaterials/Drugs/ArthritisAdvisoryCommittee/ucm286552.htm.
   Google Scholar
• Thorarensen A , BankerME, FensomeAet al. ATP mediated kinome selectivity – The missing link in understanding the contribution ofindividual JAK kinases isoforms to cellular signaling. ACS Chemical Biology9 (7), 1552–1558 (2014).
   PubMed Web of Science ®Google Scholar
• Clark JD , FlanaganME, TelliezJ-B. Discovery and development of janus kinase (JAK) inhibitors for inflammatory diseases. J. Med. Chem. 26; 57 (12): 5023–5038 (2014).
   PubMed Web of Science ®Google Scholar
• Incyte Corporation, USA : WO2010135650 (2010).
   Google Scholar
• Incyte Corporation, USA : WO2011112662 (2011).
   Google Scholar
• Incyte Corporation, USA : WO2011028685 (2011).
   Google Scholar
• Incyte Corporation, USA : WO2012068440 (2012).
   Google Scholar
• Yu V , PistilloJ, ArchibequeIet al. Differential selectivity of JAK2 inhibitors in enzymatic and cellular settings. Exp. Hematol.41 (5), 491–500 (2013).
   PubMed Web of Science ®Google Scholar
• Flanagan ME , BlumenkopfTA, BrissetteWHet al. Discovery of CP-690,550: a potent and selective Janus kinase (JAK) inhibitor for the treatment of autoimmune diseases and organ transplant rejection. J. Med. Chem.53 (24), 8468–8484 (2010).
   PubMed Web of Science ®Google Scholar
• Galapagos . www.glpg.com/.
   Google Scholar
• Vanhoutte F , van der aaA, WigerinkP, van't KloosterG. Selective JAK1 Inhibition in the Treatment of Rheumatoid Arthritis: Proof of Concept with GLPG0634. ACR 2012, Washington, DC, USA, (2012). www.glpg.com/index.php/randd/pipeline/glpg0634-ra/.
   Google Scholar
• Namour F , GalienR, VanhoutteF, WigerinkP, van't KloosterG. An active metabolite contributes to the pharmacodynamics and efficacy of GLPG0634, a selective JAK1 inhibitor. Presented at : ACR 2013 Annual Meeting. San Diego, CA, USA, 26–30 October 2013.
   Google Scholar
• Incyte Reports 2013 Fourth-Quarter and Year-End Financial Results; Provides 2014 Financial Guidance; Updates Shareholders on Key Clinical Programs, Press Release. http://investor.incyte.com/phoenix.zhtml?c=69764&p=irol-reportsannual.
   Google Scholar
• luchi M , Fidelus-GortD, DouglasHet al. A randomized, dose-ranging, placebo- controlled 84-day (12-week)study of INCB039110, a selective Janus Kinase-1 Inhibitor in patients with active rheumatoid arthritis. Presented at : ACR 2013 Annual Meeting. San Diego, CA, USA, 26–30 October 2013.
   Google Scholar
• Goedken E . Covalent inhibitors selectively target Jak3 through an active-site thiol. Presented at : Protein Kinases in Drug Discovery. Berlin, Germany, 8–9 May 2014.
   Google Scholar
• Van Epps S , FiamengoB, EdmundsJet al. Design and synthesis of tricyclic cores for kinase inhibition. Bioorg. Med. Chem. Lett.23 (3), 693–698 (2013).
   PubMed Web of Science ®Google Scholar
• Voss J , GraffC, schwartzAet al. Pharmacodynamics of a novel Jak1 selective inhibitor in rat arthritis and anemia models and in healthy human subjects. Presented at : ACR 2013 Annual Meeting. San Diego, CA, USA, 26–30 October 2013. www.dekanat.med.uni-erlangen.de/e4158/e4383/e4384/inhalt4395/Forschungsbericht2013-englisch.pdf.
   Google Scholar
• Ungureanu D , WuJ, PekkalaTet al. The pseudokinase domain of JAK2 is a dual-specificity protein kinase that negatively regulates cytokine signaling. Nat. Struct. Mol. Biol.18 (9), 971–976 (2011).
   PubMed Web of Science ®Google Scholar
• Boggon TJ , LiY, ManleyPW, EckMJ. Crystal structure of the Jak3 kinase domain in complex with a staurosporineanalog. Blood106 (3), 996–1002 (2005).
   PubMed Web of Science ®Google Scholar
• Lucet IS , FantinoE, StylesMet al. The structural basis of Janus kinase 2 inhibition by a potent and specific pan-Janus kinase inhibitor. Blood107 (1), 176–183 (2006).
   PubMed Web of Science ®Google Scholar
• Williams NK , BamertRS, PatelOet al. Dissecting specificity in the janus kinases: the structures of JAK-specific inhibitors complexed to the JAK1 and JAK2 protein tyrosine kinase domains. J. Mol. Biol.387 (1), 219–232 (2009).
   PubMed Web of Science ®Google Scholar
• Chrencik JE , PatnyA, LeungIKet al. Structural and thermodynamic characterization of the TYK2 and JAK3 kinase domains in complex with CP-690550 and CMP-6. J. Mol. Biol.400 (3), 413–433 (2010).
   PubMed Web of Science ®Google Scholar
• Malerich JP , LamJS, HartBet al. Diamino-1,2,4-triazole derivatives are selective inhibitors of TYK2 and JAK1 over JAK2 and JAK3. Bioorg. Med. Chem. Lett.20 (24), 7454–7457 (2010).
   PubMed Web of Science ®Google Scholar
• Ledeboer MW , PierceAC, DuffyJPet al. 2-Aminopyrazolo[1,5-a]pyrimidines as potent and selective inhibitors of JAK2. Bioorg. Med. Chem. Lett.19 (23), 6529–6533 (2009).
   PubMed Web of Science ®Google Scholar
• Menet C . First Selective JAK1 Inhibitor: GLPG0634 from Hit to Proof of Concept. Protein Kinase 2012, Cambridge, UK, 2012.
   Google Scholar
• Galapagos NV : WO2010010186 (2010).
   Google Scholar
• Galapagos NV : WO2010010187 (2010).
   Google Scholar
• Galapagos NV : WO2010010190 (2010).
   Google Scholar
• Galapagos NV : WO2010010191 (2010).
   Google Scholar
• Galapagos NV : WO2010149769 (2010).
   Google Scholar
• Galapagos NV : WO2010149771 (2010).
   Google Scholar
• Galapagos NV : WO2012146659 (2012).
   Google Scholar
• Galapagos NV : WO2010010184 (2010).
   Google Scholar
• Galapagos NV : WO2010010188 (2010).
   Google Scholar
• Galapagos NV : WO2010010189 (2010).
   Google Scholar
• Galapagos NV : WO2012146657 (2010).
   Google Scholar
• Galapagos NV : WO2013117645 (2010).
   Google Scholar
• Galapagos NV : WO2013117649 (2010).
   Google Scholar
• Siu M , PastorR, LiuWet al. 2-Amino-[1,2,4]triazolo[1,5-a]pyridines as JAK2 inhibitors. Bioorg. Med. Chem. Lett.23 (17), 5014–5021 (2013).
   PubMed Web of Science ®Google Scholar
• Kulagowski JJ , BlairW, BullRJet al. Identification of imidazo-pyrrolopyridines as novel and potent JAK1 inhibitors. J. Med. Chem.55 (12), 5901–5921 (2012).
   PubMed Web of Science ®Google Scholar
• Zak M , MendoncaR, BalazsMet al. Discovery and optimization of C-2 methyl imidazopyrrolopyridines as potent and orally bioavailable JAK1 inhibitors with selectivity over JAK2. J. Med. Chem.55 (13), 6176–6193 (2012).
   PubMed Web of Science ®Google Scholar
• Zak M , HurleyCA, WardSIet al. Identification of C-2 hydroxyethylimidazopyrrolopyridines as potent JAK1 inhibitors with favorable physicochemical properties and high selectivity over JAK2. J. Med. Chem.56 (11), 4764–4785 (2013).
   PubMed Web of Science ®Google Scholar
• Labadie S , DragovichPS, BarrettKet al. Structure-based discovery of C-2 substituted imidazo-pyrrolopyridine JAK1 inhibitors with improved selectivity over JAK2. Bioorg. Med. Chem. Lett.22 (24), 7627–7633 (2012).
   PubMed Web of Science ®Google Scholar
• Hurley CA , BlairWS, BullRJet al. Novel triazolo-pyrrolopyridines as inhibitors of Janus kinase 1. Bioorg. Med. Chem. Lett.23 (12), 3592–3598 (2013).
   PubMed Web of Science ®Google Scholar
• F. Hoffmann-La Roche Ag : WO2011086053 (2011).
   Google Scholar
• Norman P . Selective JAK1 inhibitor and selective Tyk2 inhibitor patents. Expert Opin. Ther. Pat.22 (10), 1233–1249 (2012).
   PubMed Web of Science ®Google Scholar
• F. Hoffmann-La Roche Ag : WO2013007768 (2013).
   Google Scholar
• F. Hoffmann-La Roche Ag : WO2013007765 (2013).
   Google Scholar
• F. Hoffmann-La Roche Ag : WO2012085176 (2012).
   Google Scholar
• Advinus Therapeutics, Ltd : WO2012127506 (2012).
   Google Scholar
• Abbott Laboratories : WO2009152133 (2009).
   Google Scholar
• Abbott Laboratories : WO2011068881 (2011).
   Google Scholar
• Advinus Therapeutics, Ltd : WO2014045305 (2014).
   Google Scholar
• Nissan Chemical Industries, Ltd : WO2013024895 (2013).
   Google Scholar
• Incyte Corporation, USA : US20140121198 (2014).
   Google Scholar
• Kulagowski JJ , BlairW, BullRJet al. Identification of imidazo-pyrrolopyridines as novel and potent JAK1 inhibitors. J. Med. Chem.55 (12), 5901–5921 (2012).
   PubMed Web of Science ®Google Scholar
• Incyte Corporation, USA : US20070135461 (2007).
   Google Scholar
• Quintás-Cardama A , VaddiK, LiuPet al. Preclinical characterization of the selective JAK1/2 inhibitor INCB018424: therapeutic implications for the treatment of myeloproliferative neoplasms. Blood115 (15), 3109–3117 (2010).
   PubMed Web of Science ®Google Scholar
• Fridman JS , ScherlePA, CollinsRet al. Selective inhibition of JAK1 and JAK2 is efficacious in rodent models of arthritis: preclinical characterization of INCB028050. J. Immunol. Baltim. Md 1950.184 (9), 5298–307 (2010).
   Google Scholar
• Incyte Corporation, USA : WO2012068450 (2012).
   Google Scholar
• Incyte Corporation, USA : WO2012177606 (2012).
   Google Scholar
• Incyte Corporation, USA : WO2013026025 (2013).
   Google Scholar
• Incyte Corporation, USA : WO2013173720 (2013).
   Google Scholar
• Norman P . Selective JAK inhibitors in development for rheumatoid arthritis. Expert Opin. Investig. Drugs.23 (8), 1067–1077 (2014).
   PubMed Web of Science ®Google Scholar
• Pfizer Inc : WO2010020905 (2010).
   Google Scholar
• Merck & Co., Inc., USA : WO2013040863 (2013).
   Google Scholar
• Merck & Co., Inc., USA : WO2013041042 (2013).
   Google Scholar
• Merck & Co., Inc., USA : WO2013043962 (2013).
   Google Scholar
• Merck & Co., Inc., USA : WO2013043964 (2013).
   Google Scholar
• Pfizer Inc : WO2011045702 (2011).
   Google Scholar
• Pfizer Inc : WO2011075334 (2011).
   Google Scholar
• Hutchison Medipharma Ltd : WO2012022045 (2012).
   Google Scholar
• Norman P . Evaluation of WO-2013040863, WO-2013041042 and WO-2013043962. Selective JAK1 inhibitors based on a 3-aminopyrazole-4-carboxamide scaffold. Exp. Opin. Ther. Pat.24 (2), 231–237 (2014).
   PubMed Web of Science ®Google Scholar
• Merck & Co., Inc. USA : WO2010014453 (2010).
   Google Scholar
• Exelixis, Inc : WO2012037132 (2012).
   Google Scholar
• Norman P . Evaluation of WO2012037132 – a novel scaffold for selective JAK1 inhibition. Expert Opin. Ther. Pat.22 (9), 1105–1109 (2012).
   PubMed Web of Science ®Google Scholar
• Cellzome, Ltd : WO2013092854 (2013).
   Google Scholar
• Kim MK , ShinH, ChoSY, ChongY. Linear propargylic alcohol functionality attached to the indazole-7-carboxamide as a JAK1-specific linear probe group. Bioorg. Med. Chem.22 (3), 1156–1162 (2014).
   PubMed Web of Science ®Google Scholar
• Piatnitski EL , DunctonMAJ, KiselyovASet al. Arylphthalazines: identification of a new phthalazinechemotype as inhibitors of VEGFR kinase. Bioorg. Med. Chem. Lett.15 (21), 4696–4698 (2005).
   PubMed Web of Science ®Google Scholar