1,575
Views
4
CrossRef citations to date
0
Altmetric
Research Paper

Optimisation of novel 4, 8-disubstituted dihydropyrimido[5,4-b][1,4]oxazine derivatives as potent GPR 119 agonists

, , , , , , , , & show all
Pages 50-58 | Received 11 Sep 2019, Accepted 10 Oct 2019, Published online: 28 Oct 2019

References

  • Skyler JS. Diabetes mellitus: pathogenesis and treatment strategies. J Med Chem 2004;47:4113–7.
  • Nieto A, Fernández-Vega V, Spicer TP, et al. Identification of novel, structurally diverse, small molecule modulators of gpr119. Assay Drug Dev Techn 2018;16:278–88.
  • Lan J, Zhao Y, Dong F, et al. Meta-analysis of the effect and safety of berberine in the treatment of type 2 diabetes mellitus, hyperlipemia and hypertension. J Ethnopharmacol 2015;161:69–81.
  • Campbell PT, Newton CC, Patel AV, et al. Diabetes and cause-specific mortality in a prospective cohort of one million U.S. adults. Diabetes Care 2012;35:1835–44.
  • Koro CE, Bowlin SJ, Bourgeois N, et al. Glycemic control from 1988 to 2000 among U.S. adults diagnosed with type 2 diabetes a preliminary report. Diabetes Care 2004;27:17–20.
  • Fang Y, Yang Z, Gundeti S, et al. Novel 5-nitropyrimidine derivatives bearing endo-azabicyclic alcohols/amines as potent GPR119 agonists. Bioorgan Med Chem 2017;25:254–60.
  • Wacker DA, Wang Y, Broekema M, et al. Discovery of BMS-903452, an anti-diabetic clinical candidate targeting GPR119. Clinical and Translational Imaging 2014;57:7499.
  • Scott JS, Bowker SS, Brocklehurst KJ, et al. Circumventing seizure activity in a series of G protein coupled receptor 119 (GPR119) agonists. J Med Chem 2014;57:8984–98.
  • Yang Z, Fang Y, Park H. Synthesis and biological evaluation of pyrimidine derivatives with diverse azabicyclic ether/amine as novel GPR119 agonist. Bioorg Med Chem Lett 2017;27:2515–9.
  • Kaushik AC, Kumar A, Rehman AU, et al. Deciphering G-Protein-Coupled Receptor 119 Agonists as Promising Strategy against Type 2 Diabetes Using Systems Biology Approach. ACS Omega 2018;3:18214–26.
  • Overton HA, Fyfe MCT, Reynet C. GPR119, a novel G protein-coupled receptor target for the treatment of type 2 diabetes and obesity. Br J Pharmacol 2009;153:S76–S81.
  • Han T, Lee BM, Park YH, et al. YH18968, a novel 1,2,4-triazolone G-protein coupled receptor 119 agonist for the treatment of type 2 diabetes mellitus. Biomol Ther 2018;26:201–9.
  • Koshizawa T, Morimoto T, Watanabe G, et al. Optimization of a novel series of potent and orally bioavailable GPR119 agonists. Bioorg Med Chem Lett 2017;27:3249–53.
  • Zhou Y, Zhu X, Zhang L, et al. Design, synthesis, and biological evaluation of 2-(4-(methylsulfonyl)phenyl)pyridine derivatives as GPR119 agonists. Chem Biol Drug Des 2019;93:67–74.
  • Gao J, Tian L, Weng G, et al. Stimulating beta cell replication and improving islet graft function by GPR119 agonists. Transpl Int 2011;24:1124–34.
  • Fyfe MC, McCormack JG, Overton HA, et al. GPR119 agonists as potential new oral agents for the treatment of type 2 diabetes and obesity. Expert Opin Drug Dis 2008;3:403–13.
  • Yoshida S, Ohishi T, Matsui T, et al. The role of small molecule GPR119 agonist, AS1535907, in glucose‐stimulated insulin secretion and pancreatic β‐cell function. Diabetes Obes Metab 2011;13:34–41.
  • Matsuda D, Kawamura M, Kobashi Y, et al. Design, synthesis and biological evaluation of novel 7-azaspiro[3,5]nonane derivatives as GPR119 agonists. Bioorgan Med Chem 2018;26:1832–47.
  • Zhu C, Wang L, Zhu Y, et al. Discovery of phenyl acetamides as potent and selective GPR119 agonists. Bioorg Med Chem Lett 2017;27:1124–8.
  • Li G, Huan Y, Yuan BK, et al. Discovery of novel xanthine compounds targeting DPP-IV and GPR119 as anti-diabetic agents. Eur J Med Chem 2016;124:103–16.
  • Jang YK, Lee KM, Jung K, et al. Design, synthesis, and biological evaluation of aryl N-methoxyamide derivatives as GPR119 agonists. Bioorg Med Chem Lett 2017;27:3909–14.
  • Matsuda D, Kobashi Y, Mikami A, et al. Novel 3 H-[1,2,3]triazolo[4,5- c]pyridine derivatives as GPR119 agonists: Synthesis and structure-activity/solubility relationships. Bioorgan Med Chem 2017;25:4339–54.
  • Harada K, Mizukami J, Kadowaki S, et al. Design and synthesis of novel and potent GPR119 agonists with a spirocyclic structure. Bioorg Med Chem Lett 2018;28:1228–33.
  • Han S, Narayanan S, Sun HK, et al. Discovery of a novel trans-1,4-dioxycyclohexane GPR119 agonist series. Bioorg Med Chem Lett 2015;25:3034–8.
  • Neelamkavil SF, Stamford AW, Kowalski T, et al. Discovery of MK-8282 as a potent G-protein-coupled receptor 119 agonist for the treatment of type 2 diabetes. Acs Med Chem Lett 2018;9:457–61.
  • Ritter K, Buning C, Halland N, et al. G protein-coupled receptor 119 (gpr119) agonists for the treatment of diabetes: recent progress and prevailing challenges. J Med Chem 2016;59:3579–92.
  • Wacker DA, Wang Y, Broekema M, et al. Discovery of 5-chloro-4-((1-(5-chloropyrimidin-2-yl)piperidin-4-yl)oxy)-1-(2-fluoro-4-(methylsulfonyl)phenyl)pyridin-2(1h)-one (BMS-903452), an antidiabetic clinical candidate targeting GPR119. J Med Chem 2014;57:7499–508.
  • Semple G, Fioravanti B, Pereira G, et al. Discovery of the First Potent and Orally Efficacious Agonist of the Orphan G-Protein Coupled Receptor 119. J. Med. Chem 2008;51:5172–5.
  • Liu P, Hu Z, Dubois BG, et al. Design of potent and orally active GPR119 agonists for the treatment of type ii diabetes. Acs Med Chem Lett 2015;6:936–41.
  • Yang Z, Fang Y, Pham TN, et al. Synthesis and biological evaluation of 5-nitropyrimidine analogs with azabicyclic substituents as GPR119 agonists. Bioorg Med Chem Lett 2013;23:1519–21.
  • Fang Y, Jun X, Zhifeng L, et al. Design and synthesis of novel pyrimido[5,4-d]pyrimidine derivatives as GPR119 agonist for treatment of type 2 diabetes. Bioorgan Med Chem 2018;26:4080–7.
  • Fang Y, Xiong L, Hu J, et al. Synthesis and evaluation of novel fused pyrimidine derivatives as GPR119 agonists. Bioorg Chem 2019;86:103–11.
  • Pham TAN, Yang Z, Fang Y, et al. Synthesis and biological evaluation of novel 2,4-disubstituted quinazoline analogues as GPR119 agonists. Bioorgan Med Chem 2013;21:1349–56.
  • Heidmann B, Gatfield J, Roch C, et al. Discovery of highly potent dual orexin receptor antagonists via a scaffold-hopping approach. Chemmedchem 2016;11:2132–46.
  • Ryan H; Jennifer K; Melissa F, et al. Pyrimidine compounds as JAK kinase inhibitors, Patent WO 2017189822; 2017.
  • Mastracchio A, Bruncko M, Lai C, et al. Heterocyclylpyridine derivatives as CDK9 kinase inhibitors and their preparation, Patent US 20140275011; 2014.