5-HT₇ receptor modulators: a medicinal chemistry survey of recent patent literature (2004 – 2009)

Bibliography

• Hoyer D, Clarke DE, Fozard JR, International Union of Pharmacology classification of receptors for 5-hydroxytryptamine (Serotonin). Pharmacol Rev 1994;46:157-203
   PubMed Web of Science ®Google Scholar
• Vanhoenacker P, Haegeman G, Leysen JE. 5-HT7 receptors: current knowledge and future prospects. Trends Pharmacol Sci 2000;21:70-7
   PubMed Web of Science ®Google Scholar
• Hedlund PB, Sutcliffe JG. Functional, molecular and pharmacological advances in 5-HT7 receptor research. Trends Pharmacol Sci 2004;25:481-6
   PubMed Web of Science ®Google Scholar
• To ZP, Bonhaus DW, Eglen RM, Characterization and distribution of putative 5-ht7 receptors in guinea-pig brain. Br J Pharmacol 1995;115:107-16
   PubMed Web of Science ®Google Scholar
• Mengod G, Vilaro MT, Raurich A, 5-HT receptors in mammalian brain: receptor autoradiography and in situ hybridization studies of new ligands and newly identified receptors. Histochem J 1996;28:747-58
   Google Scholar
• Waeber C, Moskowitz MA. Autoradiographic visualisation of [3H]5-carboxamidotryptamine binding sites in the guinea pig and rat brain. Eur J Pharmacol 1995;283:31-46
   PubMed Web of Science ®Google Scholar
• Gustafson EL, Durkin MM, Bard JA, A receptor autoradiographic and in situ hybridization analysis of the distribution of the 5-ht7 receptor in rat brain. Br J Pharmacol 1996;117:657-66
   PubMed Web of Science ®Google Scholar
• Bonaventure P, Nepomuceno D, Hein L, et al. Radioligand binding analysis of knockout mice reveals 5-hydroxytryptamine7 receptor distribution and uncovers 8-hydroxy-2-(di-n-propylamino)tetralin interaction with alpha2 adrenergic receptors. Neuroscience 2004;124:901-11
   Google Scholar
• Varnäs K, Thomas DR, Tupala E, Distribution of 5-HT7 receptors in the human brain: a preliminary autoradiographic study using [3H] SB-269970. Neurosci Lett 2004;367:313-6
   Google Scholar
• Neumaier JF, Sexton TJ, Yracheta J, Localization of 5-HT7 receptors in rat brain by immunocytochemistry, in situ hybridization, and agonist stimulated cFos expression. J Chem Neuroanat 2001;21:63-73
   PubMed Web of Science ®Google Scholar
• Belenky MA, Pickard GE. Subcellular distribution of 5-HT1B and 5-HT7 receptors in the mouse suprachiasmatic nucleus. J Comp Neurol 2001;432:371-88
   Google Scholar
• Doly S, Fischer J, Brisorgueil MJ, Pre- and postsynaptic localization of the 5-HT7 receptor in rat dorsal spinal cord: immunocytochemical evidence. J Comp Neurol 2005;490:256-69
   Google Scholar
• Hagan JJ, Price GW, Jeffrey P, Characterization of SB-269970-A, a selective 5-HT7 receptor antagonist. Br J Pharmacol 2000;130:539-48
   PubMed Web of Science ®Google Scholar
• Hedlund PB, Danielson PE, Thomas EA, No hypothermic response to serotonin in 5-HT7 receptor knockout mice. Proc Natl Acad Sci USA 2003;100:1375-80
   PubMed Web of Science ®Google Scholar
• Guscott M, Bristow LJ, Hadingham K, Genetic knockout and pharmacological blockade studies of the 5-HT7 receptor suggest therapeutic potential in depression. Neuropharmacology 2005;48:492-502
   PubMed Web of Science ®Google Scholar
• Sprouse J, Li X, Stock J, Circadian rhythm phenotype of 5-HT7 receptor knockout mice: 5-HT and 8-OH-DPAT-induced phase advances of SCN neuronal firing. J Biol Rhythms 2005;20:122-31
   PubMedGoogle Scholar
• Witkin JM, Baez M, Yu J, Constitutive deletion of the serotonin-7 (5-HT(7)) receptor decreases electrical and chemical seizure thresholds. Epilepsy Res 2007;75:39-45
   Google Scholar
• Hedlund PB, Sutcliffe JG. 5-HT7 receptors as favorable pharmacological targets for drug discovery. In: Roth BL, editor, The serotonin receptors: from molecular pharmacology to human therapeutics Humana Press, Totowa, NJ; 2006. p. 517-35
   Google Scholar
• Hedlund PB. The 5-HT7 receptor and disorders of the nervous system: an overview. Psychopharmacology (Berl) 2009;206:345-54
   PubMed Web of Science ®Google Scholar
• Monsma FJ, Shen Y, Ward RP, Cloning and expression of a novel serotonin receptor with high affinity for tricyclic psychotropic drugs. Mol Pharmacol 1993;43:320-7
   PubMed Web of Science ®Google Scholar
• Mullins UL, Gianutsos G, Eison AS. Effects of antidepressants on 5-HT7 receptor regulation in the rat hypothalamus. Neuropsychopharmacology 1999;21:352-67
   PubMed Web of Science ®Google Scholar
• Hedlund PB, Huitron-Resendiz S, Henriksen SJ. 5-HT7 receptor inhibition and inactivation induce antidepressant like behavior and sleep pattern. Biol Psychiatry 2005;58:831-7
   PubMed Web of Science ®Google Scholar
• Wesolowska A, Nikiforuk A, Stachowicz K, Effect of the selective 5-HT7 receptor antagonist SB-269970 in animal models of anxiety and depression. Neuropharmacology 2006;51:578-86
   PubMed Web of Science ®Google Scholar
• Wesolowska A, Nikiforuk A, Stachowicz K. Potential anxiolytic and antidepressant effects of the selective 5-HT7 receptor antagonist SB-269970 after intrahippocampal administration to rats. Eur J Pharmacol 2006;553:185-90
   PubMed Web of Science ®Google Scholar
• Wesolowska A, Tatarczynska E, Nikiforuk A, Enhancement of the anti-immobility action of antidepressants by a selective 5-HT7 receptor antagonist in the forced swimming test in mice. Eur J Pharmacol 2007;555:43-7
   PubMed Web of Science ®Google Scholar
• Bonaventure P, Kelly L, Aluisio L. Selective blockade of 5-hydroxytryptamine 5-HT7 receptors enhances 5-HT transmission, antidepressant-like behavior, and rapid eye movement sleep suppression induced by citalopram in rodents. J Pharmacol Exp Ther 2007;321:690-8
   PubMed Web of Science ®Google Scholar
• Antle MC, Ogilvie MD, Pickard GE, Response of the mouse circadian system to serotonin 1A/2/7 agonists in vivo: surprisingly little. J Biol Rhythms 2003;18:145-8
   PubMed Web of Science ®Google Scholar
• Glass JD, Grossman GH, Farnbauch L, Midbrain raphe modulation of nonphotic circadian clock resetting and 5-HT release in the mammalian suprachiasmatic nucleus. J Neurosci 2003;23:7451-60
   PubMed Web of Science ®Google Scholar
• Duncan MJ, Short J, Wheeler DL. Comparison of the effects of aging on 5-HT7 and 5-HT1A receptors in discrete regions of the circadian timing system in hamsters. Brain Res 1999;829:39-45
   Google Scholar
• Sprouse J, Reynolds L, Li X, 8-OH-DPAT as a 5-HT7 agonist: phase shifts of the circadian biological clock through increases in cAMP production. Neuropharmacology 2004;46:52-62
   PubMed Web of Science ®Google Scholar
• Lovenberg TW, Baron BM, de Lecea L, A novel adenylyl cyclase-activating serotonin receptor (5-HT7) implicated in the regulation of mammalian circadian rhythms. Neuron 1993;11:449-58
   PubMed Web of Science ®Google Scholar
• Ehlen JC, Grossman GH, Glass JD. In vivo resetting of the hamster circadian clock by 5-HT7 receptors in the suprachiasmatic nucleus. J Neurosci 2001;21:5351-7
   PubMed Web of Science ®Google Scholar
• Ying SW, Rusak B. 5-HT7 receptors mediate serotonergic effects on light-sensitive suprachiasmatic nucleus neurons. Brain Res 1997;755:246-54
   PubMed Web of Science ®Google Scholar
• Yu GD, Liu YL, Jiang XH, The inhibitory effect of serotonin on the spontaneous discharge of suprachiasmatic neurons in hypothalamic slice is mediated by 5-HT7 receptor. Brain Res Bull 2001;54:395-8
   Google Scholar
• Gardani M, Biello S. The effects of photic and nonphotic stimuli in the 5-HT7 receptor knockout mouse. Neuroscience 2008;152:245-53
   PubMed Web of Science ®Google Scholar
• Thomas DR, Melotto S, Massagrande M, SB-656104-A, a novel selective 5-HT7 receptor antagonist, modulates REM sleep in rats. Br J Pharmacol 2003;139:705-14
   Google Scholar
• Roberts AJ, Krucker T, Levy CL, Mice lacking 5-HT7 receptors show specific impairments in contextual learning. Eur J Neurosci 2004;19:1913-22
   Google Scholar
• Sarkisyan G, Hedlund PB. The 5-HT7 receptor is involved in allocentric spatial memory information processing. Behav Brain Res 2009;202:26-31
   Google Scholar
• Perez-García GS, Meneses A. Effects of the potential 5-HT7 receptor agonist AS 19 in an autoshaping learning task. Behav Brain Res 2005;163:136-40
   Google Scholar
• Johnson KW, Schaus JM, Durkin MM, 5-HT1F receptor agonists inhibit neurogenic dural inflammation in guinea pigs. Neuroreport 1997;8:2237-40
   PubMed Web of Science ®Google Scholar
• Ullmer C, Schmuck K, Kalkman HO, Expression of serotonin receptor mRNAs in blood vessels. FEBS Lett 1995;370:215-21
   PubMed Web of Science ®Google Scholar
• Schoeffter P, Ullmer C, Bobirnac I, Functional, endogenously expressed 5-hydroxytryptamine 5-HT7 receptors in human vascular smooth muscle cells. Br J Pharmacol 1996;117:993-4
   Google Scholar
• Verheggen R, Meier A, Werner I, Functional 5-HT receptors in human occipital artery. Naunyn Schmiedebergs Arch Pharmacol 2004;369:391-401
   Google Scholar
• Terrón JA, Falcón-Neri A. Pharmacological evidence for the 5-HT7 receptor mediating smooth muscle relaxation in canine cerebral artery. Br J Pharmacol 1999;127:609-16
   PubMed Web of Science ®Google Scholar
• Villalon CM, Centurion D, Lujan-Estrada M, Mediation of 5-HT-induced external carotid vasodilatation in GR 127935-pretreated vagosympathectomized dogs by the putative 5-HT7 receptor. Br J Pharmacol 1997;120:1319-27
   PubMed Web of Science ®Google Scholar
• Terrón JA, Martínez-García E. 5-HT7 receptor-mediated dilatation in the middle meningeal artery of anesthetized rats. Eur J Pharmacol 2007;560:56-60
   PubMed Web of Science ®Google Scholar
• Martínez-García E, García-Iglesias B, Terrón JA. Effect of central serotonin depletion on 5-HT receptor-mediated vasomotor responses in the middle meningeal artery of anaesthetized rats. Auton Autacoid Pharmacol 2009;29:43-50
   Google Scholar
• Dogrul A, Seyrek M. Systemic morphine produce antinociception mediated by spinal 5-HT7, but not 5-HT1A and 5-HT2 receptors in the spinal cord. Br J Pharmacol 2009;149:498-505
   Google Scholar
• Brenchat A, Romero L, García M, 5-HT7 receptor activation inhibits mechanical hypersensitivity secondary to capsaicin sensitization in mice. Pain 2009;141:239-47
   PubMedGoogle Scholar
• Diaz-Reval MI, Ventura-Martinez R, Deciga-Campos M, Evidence for a central mechanism of action of S-(+)-ketoprofen. Eur J Pharmacol 2004;483:241-8
   PubMed Web of Science ®Google Scholar
• Harte SE, Kender RG, Borszcz GS. Activation of 5-HT1A and 5-HT7 receptors in the parafascicular nucleus suppresses the affective reaction of rats to noxious stimulation. Pain 2005;113:405-15
   Google Scholar
• Leopoldo M. Serotonin(7) receptors (5-HT7Rs) and their ligands. Curr Med Chem 2004;11:629-61
   PubMed Web of Science ®Google Scholar
• Pittalà V, Salerno L, Modica M, 5-HT7 receptor ligands: recent developments and potential therapeutic applications. Mini Rev Med Chem 2007;7:945-60
   PubMed Web of Science ®Google Scholar
• Mitsubishi Pharma Corp. Compounds having 5-HT7 receptor antagonist activity and muscarinic M4 receptor agonist activity and their use in the treaatment of psychotic disorders. WO2004087124; 2004
   Google Scholar
• Suckling CJ, Murphy JA, Khalaf AI, M4 agonists/5HT7 antagonists with potential as antischizophrenic drugs: serominic compounds. Bioorg Med Chem Lett 2007;17:2649-55
   PubMed Web of Science ®Google Scholar
• University of Bari. N-(1,2,3,4-tetrahydronaphthalen-1-yl)-4-phenyl-1-piperazinealkylamide derivatives, and therapeutic use threof as 5-HT7 receptor ligands. US20070117811; 2007
   Google Scholar
• Leopoldo M, Berardi F, Colabufo NA, Structure-affinity relationship study on N-(1,2,3,4-tetrahydronaphthalen-1-yl)-4-aryl-1-piperazinealkylamides, a new class of 5-hydroxytryptamine7 receptor agents. J Med Chem 2004;47:6616-24
   PubMed Web of Science ®Google Scholar
• Leopoldo M, Lacivita E, Contino M, Structure-activity relationship study on N-(1,2,3,4-tetrahydronaphthalen-1-yl)-4-aryl-1-piperazinehexanamides, a class of 5-HT7 receptor agents. 2. J Med Chem 2007;50:4214-21
   PubMed Web of Science ®Google Scholar
• Pfizer Products, Inc. Quinoline derivatives. WO2004043929; 2004
   Google Scholar
• Ajinomoto Co., Inc. Novel piperidine derivatives. WO2004103972; 2004
   Google Scholar
• Merck & Co., Inc. Sulfone derivatives as 5-HT7 receptor ligands. US20040229864; 2004
   Google Scholar
• Raubo P, Beer MS, Hunt PA, Aminoalkyl phenyl sulfones-a novel series of 5-HT7 receptor ligands. Bioorg Med Chem Lett 2006;16:1255-8
   PubMedGoogle Scholar
• Egis Gyógyszergyár. Pyridine derivatives of alkyl oxindoles as 5HT7 receptor active agents. WO2005108388; 2005
   Google Scholar
• Egisy Gyógyszergyár. Piperazine derivatives of alkyl oxindoles. WO2005108363; 2005
   Google Scholar
• Volk B, Barkóczy J, Hegedus E, Phenylpiperazinyl-butyl)oxindoles as selective 5-HT7 receptor antagonists. J Med Chem 2008;51:2522-32
   PubMed Web of Science ®Google Scholar
• Egis Gyógyszergyár. New benzofuran derivatives as selective 5HT7 receptor inhibitors and process for their preparation. WO2008146064; 2008
   Google Scholar
• Eli Lilly & Co. 2-[4-(Pyrazol-4-ylalkyl)piperazin-1-yl]-3-phenyl pyrazines and pyridines and 3-[4-(pyrazol-4-ylalkyl)piperazin-1-yl]-2-phenyl pyridines as 5-HT7 receptor antagonists. WO2008141020; 2008
   Google Scholar
• Shibata M, Ohkubo T, Takahashi H, Modified formalin test: characteristic biphasic pain response. Pain 1989;38:347-52
   PubMed Web of Science ®Google Scholar
• Tjølsen A, Berge OG, Hunskaar S, The formalin test: an evaluation of the method. Pain 1992;51:5-17
   PubMed Web of Science ®Google Scholar
• Kim SH, Chung JM. An experimental model for peripheral neuropathy produced by segmental spinal nerve ligation in the rat. Pain 1992;50:355-63
   PubMed Web of Science ®Google Scholar
• Sethy VH, Oien TT. Role of cGMP in the mechanism of anxiolytic activity of U-78875. Pharmacol Biochem Behav 1991;39:379-82
   Google Scholar
• Eli Lilly & Co. 5-HT7 receptor antagonists. WO2009048765; 2009
   Google Scholar
• Eli Lilly & Co. Substituted piperazinyl pyrazines and pyridines as 5-HT7 receptor antagonists. WO2009029439; 2009
   Google Scholar
• Laboratorios del Dr Esteve SA. Heterocyclic-substituted-tetrahydro-naphthalen-amine derivatives, their preparation an use as medicaments. WO2008116663; 2008
   Google Scholar
• Laboratorios del Dr Esteve SA. Heterocyclic substituted tetrahydronaphthalene derivatives as 5-HT7 receptor ligands. WO2008095689; 2008
   Google Scholar
• Sanin A, Brisander M, Rosqvist S, 5-Aryl substituted (S)-2-(dimethylamino)-tetralins novel serotonin 5HT7 receptor ligands. Proceedings of the 14th Camerino-Noordwijkerhout symposium. Ongoing progress in the receptor chemistry, Italy; 2003. p. 27
   Google Scholar
• Holmberg P, Sohn D, Leideborg R, Novel 2-aminotetralin and 3-aminochroman derivatives as selective serotonin 5-HT7 receptor agonists and antagonists. J Med Chem 2004;47:3927-30
   PubMed Web of Science ®Google Scholar
• Laboratorios del Dr Esteve SA. Indane-amine derivatives, their preparation and use as medicaments EP2011786; 2007
   Google Scholar
• Laboratorios del Dr Esteve SA. Heterocyclyl-substituted-ethylamino-phenyl derivatives, their preparation and use as medicaments. WO2008077625; 2008
   Google Scholar
• Laboratorios del Dr Esteve SA. 5-HT7 receptor antagonists. WO2006018308; 2006
   Google Scholar
• Laboratorios del Dr Esteve SA. 5-HT7 receptor antagonsits. US20060142321; 2006
   Google Scholar
• Artigas F, Romero L, de Montigny C, Acceleration of the effect of selected antidepressant drugs in major depression by 5-HT1A antagonists. Trends Neurosci 1996;19:378-83
   PubMed Web of Science ®Google Scholar
• Available from: http://www.pgxhealth.com/development/vilazodone.cfm [Last accessed 24 February 2010]
   Google Scholar
• Abbas AI, Hedlund PB, Huang XP, Amisulpride is a potent 5-HT7 antagonist: relevance for antidepressant actions in vivo. Psychopharmacology (Berl) 2009;205:119-28
   PubMed Web of Science ®Google Scholar
• Ruat M, Traiffort E, Leurs R, Molecular cloning, characterization, and localization of a high-affinity serotonin receptor (5-HT7) activating cAMP formation. Proc Natl Acad Sci USA 1993;90:8547-51
   PubMed Web of Science ®Google Scholar