Synthesis of GR 125487, a selective 5-HT₄ receptor antagonist

References

• Bureau, R.; Boulouard, M.; Dauphin, F.; Lezoualc’h, F.; Rault, S. Review of 5-HT4R ligands: State of art and clinical applications. Curr. Top. Med. Chem. 2010, 10, 527–553.
   PubMed Web of Science ®Google Scholar
• Modica, M. N.; Pittala, V.; Romeo, G.; Salerno, L.; Siracusa, M. A. Serotonin 5-HT3 and 5-HT4 ligands: An update of medicinal chemistry research in the past few years. Curr. Med. Chem. 2010, 17(4), 334–362.
   PubMed Web of Science ®Google Scholar
• Mohler, E. G.; Shacham, S.; Noiman, S.; Lezoualc’h, F.; Robert, S.; Gastineau, M.; Rutkowski, J.; Marantz, Y.; Dumuis, A.; Bockaert, J.; Gold, P.E.; Ragozzino, M. E. VRX-03011, a novel 5-HT4 agonist, enhances memory and hippocampal acetylcholine efflux. Neuropharmacology 2007, 53, 563–573.
   PubMed Web of Science ®Google Scholar
• Robert, S. J.; Zugaza, J. L.; Fischmeister, R.; Gardier, A. M.; Lezoualc’h, F. The human serotonin 5-HT4 receptor regulates secretion of non-amyloidogenic precursor protein. J. Biol. Chem. 2001, 276, 44881–44888.
   PubMed Web of Science ®Google Scholar
• Cachard-Chastel, M.; Lezoualc’h, F.; Dewachter, I.; Deloménie, C.; Croes, S.; Devijver, H.; Langlois, M.; Van Leuven, F.; Sicsic, S.; Gardier, A. M. 5-HT4 receptor agonists increase sAPPalpha levels in the cortex and hippocampus of male C57BL/6j mice. Br. J. Pharmacol. 2007, 150, 883–892.
   PubMed Web of Science ®Google Scholar
• Giannoni, P.; Gaven, F.; de Bundel, D.; Baranger, K.; Marchetti-Gauthier, E.; Roman, F. S.; Valjent, E.; Marin, P.; Bockaert, J.; Rivera, S.; Claeysen, S. Early administration of RS 67333, a specific 5-HT4 receptor agonist, prevents amyloidogenesis and behavioral deficits in the 5XFAD mouse model of Alzheimer’s disease. Front Aging Neurosci. 2013, 5, 96.
   PubMed Web of Science ®Google Scholar
• Manabe, N.; Wong, B. S.; Camilleri, M. New-generation 5-HT4 receptor agonists: Potential for treatment of gastrointestinal motility disorders. Expert Opin. Investig. Drugs, 2010, 19, 765–775.
   PubMed Web of Science ®Google Scholar
• De Maeyer, J. H.; Lefebvre, R. A.; Schuurkes, J. A. 5-HT4 receptor agonists: Similar but not the same. Neurogastroenterol. Motil. 2008, 20, 99–112.
   PubMed Web of Science ®Google Scholar
• Prins, N. H.; van der Grijn; Lefebvre, R. A.; Akkermans, L. M. A.; Schuurkes, J. A. J. 5-HT4 receptors mediating enhancement of contractility in canine stomach: An in vitro and in vivo study. Br. J. Pharmacol. 2001, 132, 1941–1947.
   PubMed Web of Science ®Google Scholar
• Grossman, C. J.; Gale, J. D.; Bunce, K. T.; Kilpatrick, G. J.; Whitehead, J. F.; Oxford, A. W.; Humphrey, P. P. A. Development of a radioligand binding assay for the 5-HT4 receptor: Use of a novel antagonist. Br. J. Pharmucol. 1993, 109, 618–624.
   PubMed Web of Science ®Google Scholar
• Oxford, A. W.; Whitehead, J. W. F.; Knight, J. 3-Piperidinylmethylcarboxylate-substituted indoles. PCT Pat. Appl. WO1992/014727, 3 Sep. 1992.
   Google Scholar
• Nirogi, R.; Mohammed, A. R.; Yarlagadda, S.; Ravella, S. R.; Shinde, A. K.; Kambhampati, R.; Roayapalley, P. K.; Jayarajan, P.; Bhyrapuneni, G.; Patnala, S. M.; Ravula, J.; Jasti, V. Heteroaryl compounds as 5-HT4 receptor ligands. PCT Pat. Appl. WO2013/042135 A1, 28 Mar. 2013.
   Google Scholar
• Nirogi, R.; Mohammed, A. R.; Ahmad, I.; Jayarajan, P.; Kandikere, N. V.; Shinde, A. K.; Kambhampati, R.; Bhyrapuneni, G.; Ravula, J.; Patnala, S. M.; Jasti, V. L-Dihydro-2-oxoquinoline compounds as 5-HT4 receptor ligands. PCT Pat. Appl. WO2011/030349 A1, 17 Mar. 2011.
   Google Scholar
• Nirogi, R.; Mohammed, A. R.; Shinde, A. K.; Gagginapally, S. R.; Jasti, V. Indazole compounds as 5-HT4 receptor agonists. PCT Pat. Appl. WO2015/092804 A1, 25 Jun. 2015.
   Google Scholar
• Nirogi, R.; Shinde, A. K.; Jasti, V. 5-Amino-quinoline-8-carboxamide derivatives as 5-HT4 receptor agonists. PCT Pat. Appl. WO2014/147636 A1, 25 Sep. 2014.
   Google Scholar
• Letty, S.; Child, R.; Dumuis, A.; Pantaloni, A.; Bockaert, J.; Rondouin, G. 5-HT4 receptors improve social olfactory memory in the rat. Neuropharmacol. 1997, 36, 681–687.
   PubMed Web of Science ®Google Scholar
• Marchetti-Gauthier, E.; Roman, F. S.; Dumuis, A.; Bockaert, J.; Soumireu-Mourat, B. BIMU1 increases associative memory in rats by activating 5-HT4 receptors. Neuropharmacol. 1997, 36, 697–706.
   PubMed Web of Science ®Google Scholar
• Engqvista, R.; Bergmana, J. Synthesis of benzothiopyrano[2,3-b]indol-11-one and benzopyrano[2,3-b]indol-11-one. Tetrahedron 2003, 59, 9649–9653.
   Web of Science ®Google Scholar
• Lezoualc’h, F.; Berthouze, M. 5-HT3 and 5-HT4 receptors as targets for drug discovery for dementia. In The Serotonin Receptors: From Molecular Pharmacology to Human Therapeutics; B. L. Roth (Ed.); Humana Press: Totowa, NJ, 2006; pp. 459–479.
   Google Scholar
• Bockaert, J.; Claeysen, S.; Compan, V.; Dumuis, A. 5-HT4 Receptors. Curr. Drug Targets 2004, 3, 39–51.
   Google Scholar
• Matsumoto, M.; Togashi, H.; Mori, K.; Ueno, K.; Ohashi, S.; Kojima, T.; Yoshioka, M. Evidence for involvement of central 5-HT4 receptors in cholinergic function associated with cognitive processes: Behavioral, electrophysiological, and neurochemical studies. J. Pharmacol. Exp. Ther. 2001, 296, 676–682.
   PubMed Web of Science ®Google Scholar
• Lamirault, L.; Simon, H. Enhancement of place and object recognition memory in young adult and old rats by RS 67333, a partial agonist of 5-HT4 receptors. Neuropharmacol. 2001, 41, 844–853.
   PubMed Web of Science ®Google Scholar
• Ennaceur, A.; Delacour, J. A new one-trial test for neurobiological studies of memory in rats, 1: Behavioural data. Behav. Brain Res. 1988, 31, 47–59.
   PubMed Web of Science ®Google Scholar
• Nirogi, R.; Bhyrapuneni, G.; Kandikere, V.; Benade, V.; Muddana, N.; Saralaya, R. Concurrent administration of atypical antipsychotics and donepezil: Drug interaction study in rats. Eur. J. Drug. Metab. Pharmacokinet. 2012, 37, 155–161.
   Web of Science ®Google Scholar
• Consolo, S.; Arnaboldi, S.; Giorgi, S.; Russi, G.; Ladinsky, H. 5-HT4 receptor stimulation facilitates acetylcholine release in rat frontal cortex. Neuro. Rep. 1994, 5, 1230–1232.
   PubMed Web of Science ®Google Scholar