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AMPA receptor positive allosteric modulators: a patent review

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Pages 615-628 | Published online: 13 Feb 2013

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Mathias Zink & Christoph U Correll. (2015) Glutamatergic agents for schizophrenia: current evidence and perspectives. Expert Review of Clinical Pharmacology 8:3, pages 335-352.
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Pierre Francotte, Yasmin Bay, Eric Goffin, Thomas Colson, Cindy Lesenfants, Jerzy Dorosz, Saara Laulumaa, Pierre Fraikin, Pascal de Tullio, Caroline Beaufour, Iuliana Botez, Darryl S. Pickering, Karla Frydenvang, Laurence Danober, Anders Skov Kristensen, Jette Sandholm Kastrup & Bernard Pirotte. (2023) Exploring thienothiadiazine dioxides as isosteric analogues of benzo- and pyridothiadiazine dioxides in the search of new AMPA and kainate receptor positive allosteric modulators. European Journal of Medicinal Chemistry, pages 116036.
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Dmitry A. Vasilenko, Nadezhda S. Temnyakova, Sevastian E. Dronov, Eugene V. Radchenko, Yuri K. Grishin, Alexey V. Gabrel’yan, Vladimir L. Zamoyski, Vladimir V. Grigoriev, Elena B. Averina & Vladimir A. Palyulin. (2023) 5-Nitroisoxazoles in SNAr Reactions: A Novel Chemo- and Regioselective Approach to Isoxazole-Based Bivalent Ligands of AMPA Receptors. International Journal of Molecular Sciences 24:22, pages 16135.
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Elena A. Golubeva, Mstislav I. Lavrov, Polina N. Veremeeva, Tatiana V. Vyunova, Konstantin V. Shevchenko, Maxim A. Topchiy, Andrey F. Asachenko & Vladimir A. Palyulin. (2023) New Allosteric Modulators of AMPA Receptors: Synthesis and Study of Their Functional Activity by Radioligand-Receptor Binding Analysis. International Journal of Molecular Sciences 24:12, pages 10293.
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Eric Goffin, Pierre Fraikin, Dayana Abboud, Pascal de Tullio, Caroline Beaufour, Iuliana Botez, Julien Hanson, Laurence Danober, Pierre Francotte & Bernard Pirotte. (2023) New insights in the development of positive allosteric modulators of α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptors belonging to 3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxides: Introduction of (mono/difluoro)methyl groups at the 2-position of the thiadiazine ring. European Journal of Medicinal Chemistry 250, pages 115221.
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Elena A. Golubeva, Mstislav I. Lavrov, Polina N. Veremeeva, Evgenia M. Bovina, Eugene V. Radchenko, Maxim A. Topchiy, Andrey F. Asachenko, Vladimir L. Zamoyski, Vladimir V. Grigoriev & Vladimir A. Palyulin. (2023) New 1,11-dimethyl-3,6,9-triazatricyclo[7.3.1.13,11]tetradecane-4,8,12-trione derivative as an allosteric modulator of the glutamatergic system. Mendeleev Communications 33:1, pages 70-72.
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Elena A. Golubeva, Mstislav I. Lavrov, Eugene V. Radchenko & Vladimir A. Palyulin. (2022) Diversity of AMPA Receptor Ligands: Chemotypes, Binding Modes, Mechanisms of Action, and Therapeutic Effects. Biomolecules 13:1, pages 56.
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Mstislav I. Lavrov, Polina N. Veremeeva, Elena A. Golubeva, Eugene V. Radchenko, Vladimir L. Zamoyski, Vladimir V. Grigoriev & Vladimir A. Palyulin. (2022) Positive and negative AMPA receptor modulators based on tricyclic bispidine derivative: Minor structural change inverts the type of activity. Mendeleev Communications 32:3, pages 360-363.
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Dmitry A. Vasilenko, Kirill S. Sadovnikov, Kseniya N. Sedenkova, Dmitry S. Karlov, Eugene V. Radchenko, Yuri K. Grishin, Victor B. Rybakov, Tamara S. Kuznetsova, Vladimir L. Zamoyski, Vladimir V. Grigoriev, Vladimir A. Palyulin & Elena B. Averina. (2021) A Facile Approach to Bis(isoxazoles), Promising Ligands of the AMPA Receptor. Molecules 26:21, pages 6411.
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Kasper B. Hansen, Lonnie P. Wollmuth, Derek Bowie, Hiro Furukawa, Frank S. Menniti, Alexander I. Sobolevsky, Geoffrey T. Swanson, Sharon A. Swanger, Ingo H. Greger, Terunaga Nakagawa, Chris J. McBain, Vasanthi Jayaraman, Chian-Ming Low, Mark L. Dell’Acqua, Jeffrey S. Diamond, Chad R. Camp, Riley E. Perszyk, Hongjie Yuan & Stephen F. Traynelis. (2022) Structure, Function, and Pharmacology of Glutamate Receptor Ion Channels. Pharmacological Reviews 73:4, pages 1469-1658.
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Trevor W. Stone. (2021) Relationships and Interactions between Ionotropic Glutamate Receptors and Nicotinic Receptors in the CNS. Neuroscience 468, pages 321-365.
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Koffi Sénam Etsè, Guillermo Zaragoza & Kodjo Djidjolé Etsè. (2021) Easy preparation of novel 3,3-dimethyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide: Molecular structure, Hirshfeld surface, NCI analyses and molecular docking on AMPA receptors. Journal of Molecular Structure 1238, pages 130435.
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Koffi Sénam Etsè, Jerzy Dorosz, Katrine McLain Christensen, Jean-Yves Thomas, Iuliana Botez Pop, Eric Goffin, Thomas Colson, Pierre Lestage, Laurence Danober, Bernard Pirotte, Jette Sandholm Kastrup & Pierre Francotte. (2021) Development of Thiochroman Dioxide Analogues of Benzothiadiazine Dioxides as New Positive Allosteric Modulators of α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid (AMPA) Receptors. ACS Chemical Neuroscience 12:14, pages 2679-2692.
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E.V. Radchenko, A.S. Tarakanova, D.S. Karlov, M.I. Lavrov & V.A. Palyulin. (2021) Ligands of the AMPA-subtype glutamate receptors: mechanisms of action and novel chemotypes. Biomeditsinskaya Khimiya 67:3, pages 187-200.
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Fatemeh Ashourpour, Adele Jafari & Parvin Babaei. (2021) Chronic administration of Tat-GluR23Y ameliorates cognitive dysfunction targeting CREB signaling in rats with amyloid beta neurotoxicity. Metabolic Brain Disease 36:4, pages 701-709.
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Xi Rong, Liwei Jiang, Meijie Qu, Syed Shams ul Hassan & Zongchao Liu. (2021) Enhancing Therapeutic Efficacy of Donepezil by Combined Therapy: A Comprehensive Review. Current Pharmaceutical Design 27:3, pages 332-344.
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Tatiana V. Vyunova, Lioudmila A. Andreeva, Konstantin V. Shevchenko, Vladimir V. Grigoriev, Vladimir A. Palyulin, Mstislav I. Lavrov, Ekaterina V. Bondarenko, Elena E. Kalashnikova & Nikolay F. Myasoedov. (2020) Characterization of a New Positive Allosteric Modulator of AMPA Receptors - PAM-43: Specific Binding of the Ligand and its Ability to Potentiate AMPAR Currents. Current Molecular Pharmacology 13:3, pages 216-223.
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Mstislav I. Lavrov, Oleg V. Stroganov, Vladimir L. Zamoyski, Vladimir V. Grigoriev, Maxim E. Zapolskiy, Sergey V. Sysolyatin, Valeriy V. Malykhin, Vladimir N. Surmachev & Vladimir A. Palyulin. (2020) Synthesis of an allosteric modulator of ionotropic glutamate receptors. Mendeleev Communications 30:2, pages 156-158.
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Simone Brogi, Giuseppe Campiani, Margherita Brindisi & Stefania Butini. (2019) Allosteric Modulation of Ionotropic Glutamate Receptors: An Outlook on New Therapeutic Approaches To Treat Central Nervous System Disorders. ACS Medicinal Chemistry Letters 10:3, pages 228-236.
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Katy Bernard, Sylvie Gouttefangeas, Sylvie Bretin, Stéphanie Galtier, Philippe Robert, Vjera Holthoff‐Detto, Jeffrey Cummings & Maria Pueyo. (2019) A 24‐week double‐blind placebo‐controlled study of the efficacy and safety of the AMPA modulator S47445 in patients with mild to moderate Alzheimer's disease and depressive symptoms. Alzheimer's & Dementia: Translational Research & Clinical Interventions 5:1, pages 231-240.
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Thomas Drapier, Pierre Geubelle, Charlotte Bouckaert, Lise Nielsen, Saara Laulumaa, Eric Goffin, Sébastien Dilly, Pierre Francotte, Julien Hanson, Lionel Pochet, Jette Sandholm Kastrup & Bernard Pirotte. (2018) Enhancing Action of Positive Allosteric Modulators through the Design of Dimeric Compounds. Journal of Medicinal Chemistry 61:12, pages 5279-5291.
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Marc P. Forrest, Euan Parnell & Peter Penzes. (2018) Dendritic structural plasticity and neuropsychiatric disease. Nature Reviews Neuroscience 19:4, pages 215-234.
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S. Bretin, A. Krazem, N. Henkous, C. Froger-Colleaux, E. Mocaer, C. Louis, N. Perdaems, A. Marighetto & D. Beracochea. (2017) Synergistic enhancing-memory effect of donepezil and S 47445, an AMPA positive allosteric modulator, in middle-aged and aged mice. Psychopharmacology 235:3, pages 771-787.
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Eric Goffin, Thomas Drapier, Anja Probst Larsen, Pierre Geubelle, Christopher P. Ptak, Saara Laulumaa, Karoline Rovinskaja, Julie Gilissen, Pascal de Tullio, Lars Olsen, Karla Frydenvang, Bernard Pirotte, Julien Hanson, Robert E. Oswald, Jette Sandholm Kastrup & Pierre Francotte. (2017) 7-Phenoxy-Substituted 3,4-Dihydro-2 H -1,2,4-benzothiadiazine 1,1-Dioxides as Positive Allosteric Modulators of α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid (AMPA) Receptors with Nanomolar Potency . Journal of Medicinal Chemistry 61:1, pages 251-264.
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Sylvie Bretin, Caroline Louis, Laure Seguin, Stéphanie Wagner, Jean-Yves Thomas, Sylvie Challal, Nathalie Rogez, Karine Albinet, Fabrice Iop, Nadège Villain, Sonia Bertrand, Ali Krazem, Daniel Bérachochéa, Stéphanie Billiald, Charles Tordjman, Alex Cordi, Daniel Bertrand, Pierre Lestage & Laurence Danober. (2017) Pharmacological characterisation of S 47445, a novel positive allosteric modulator of AMPA receptors. PLOS ONE 12:9, pages e0184429.
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Indira Mendez-David, Jean-Philippe Guilloux, Mariusz Papp, Laurent Tritschler, Elisabeth Mocaer, Alain M. Gardier, Sylvie Bretin & Denis J. David. (2017) S 47445 Produces Antidepressant- and Anxiolytic-Like Effects through Neurogenesis Dependent and Independent Mechanisms. Frontiers in Pharmacology 8.
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Tristan Reuillon, Simon E. Ward & Paul Beswick. 2017. Comprehensive Medicinal Chemistry III. Comprehensive Medicinal Chemistry III 447 480 .
Cinzia Citti, Umberto M. Battisti, Giuseppe Cannazza, Krzysztof Jozwiak, Natalia Stasiak, Giulia Puja, Federica Ravazzini, Giuseppe Ciccarella, Daniela Braghiroli, Carlo Parenti, Luigino Troisi & Michele Zoli. (2015) 7-Chloro-5-(furan-3-yl)-3-methyl-4 H -benzo[ e ][1,2,4]thiadiazine 1,1-Dioxide as Positive Allosteric Modulator of α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid (AMPA) Receptor. The End of the Unsaturated-Inactive Paradigm? . ACS Chemical Neuroscience 7:2, pages 149-160.
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Umberto M. Battisti, Cinzia Citti, Giulio Rastelli, Luca Pinzi, Giulia Puja, Federica Ravazzini, Giuseppe Ciccarella, Daniela Braghiroli & Giuseppe Cannazza. (2016) An unexpected reversal in the pharmacological stereoselectivity of benzothiadiazine AMPA positive allosteric modulators. MedChemComm 7:12, pages 2410-2417.
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Philip C. Biggin, Matteo Aldeghi, Michael J. Bodkin & Alexander Heifetz. 2016. The Next Generation in Membrane Protein Structure Determination. The Next Generation in Membrane Protein Structure Determination 161 181 .
G.B. Christiansen, B. Harbak, S.E. Hede, A.H. Gouliaev, L. Olsen, K. Frydenvang, J. Egebjerg, J.S. Kastrup & M.M. Holm. (2015) A novel dualistic profile of an allosteric AMPA receptor modulator identified through studies on recombinant receptors, mouse hippocampal synapses and crystal structures. Neuroscience 310, pages 709-722.
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Simon E Ward, Lewis E Pennicott & Paul Beswick. (2015) AMPA receptor-positive allosteric modulators for the treatment of schizophrenia: an overview of recent patent applications. Future Medicinal Chemistry 7:4, pages 473-491.
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Kathryn M Partin. (2015) AMPA receptor potentiators: from drug design to cognitive enhancement. Current Opinion in Pharmacology 20, pages 46-53.
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G. Brent Dawe, Mark R. Aurousseau, Bryan A. Daniels & Derek Bowie. (2015) Retour aux sources: defining the structural basis of glutamate receptor activation. The Journal of Physiology 593:1, pages 97-110.
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Pierre Francotte, Ann-Beth Nørholm, Taru Deva, Lars Olsen, Karla Frydenvang, Eric Goffin, Pierre Fraikin, Pascal de Tullio, Sylvie Challal, Jean-Yves Thomas, Fabrice Iop, Caroline Louis, Iuliana Botez-Pop, Pierre Lestage, Laurence Danober, Jette S. Kastrup & Bernard Pirotte. (2014) Positive Allosteric Modulators of 2-Amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic Acid Receptors Belonging to 4-Cyclopropyl-3,4-dihydro-2 H -1,2,4-pyridothiadiazine Dioxides and Diversely Chloro-Substituted 4-Cyclopropyl-3,4-dihydro-2 H -1,2,4-benzothiadiazine 1,1-Dioxides . Journal of Medicinal Chemistry 57:22, pages 9539-9553.
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Mathias Zink, Susanne Englisch & Andrea Schmitt. (2014) Antipsychotic treatment modulates glutamate transport and NMDA receptor expression. European Archives of Psychiatry and Clinical Neuroscience 264:S1, pages 67-82.
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Marina Maria Carrozzo, Umberto Maria Battisti, Giuseppe Cannazza, Giulia Puia, Federica Ravazzini, Aurelia Falchicchio, Serena Perrone, Cinzia Citti, Krzysztof Jozwiak, Daniela Braghiroli, Carlo Parenti & Luigino Troisi. (2014) Design, stereoselective synthesis, configurational stability and biological activity of 7-chloro-9-(furan-3-yl)-2,3,3a,4-tetrahydro-1H-benzo[e]pyrrolo[2,1-c][1,2,4]thiadiazine 5,5-dioxide. Bioorganic & Medicinal Chemistry 22:17, pages 4667-4676.
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Christopher P. Ptak, Ching-Lin Hsieh, Gregory A. Weiland & Robert E. Oswald. (2013) Role of Stoichiometry in the Dimer-Stabilizing Effect of AMPA Receptor Allosteric Modulators. ACS Chemical Biology 9:1, pages 128-133.
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Christopher L. Cioffi. (2013) Modulation of NMDA receptor function as a treatment for schizophrenia. Bioorganic & Medicinal Chemistry Letters 23:18, pages 5034-5044.
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