AMPA receptor positive allosteric modulators: a patent review

Bibliography

• Francotte P, de Tullio P, Fraikin P, In search of novel AMPA potentiators. Recent Pat CNS Drug Discov 2006;1:239-46
   PubMedGoogle Scholar
• Palmer CL, Cotton L, Henley JM. The molecular pharmacology and cell biology of R-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptors. Pharmacol Rev 2005;57:253-77
   PubMed Web of Science ®Google Scholar
• Mansour M, Nagarajan N, Nehring RB, Heteromeric AMPA receptors assemble with a preferred subunit stoichiometry and spatial arrangement. Neuron 2001;32:841-53
   PubMed Web of Science ®Google Scholar
• Robert A, Irizarry SN, Hughes TE, Howe JR. Subunit interactions and AMPA receptor desensitization. J Neurosci 2001;21:5574-86
   PubMed Web of Science ®Google Scholar
• Greger IH, Esteban JA. AMPA receptor biogenesis and trafficking. Curr Opin Neurobiol 2007;17:289-97
   PubMed Web of Science ®Google Scholar
• Armstrong N, Gouaux E. Mechanisms for activation and antagonism of an AMPA-sensitive glutamate receptor: crystal structures of the GluR2 ligand binding core. Neuron 2000;28:165-81
   PubMed Web of Science ®Google Scholar
• Gouaux E. Structure and function of AMPA receptors. J Physiol 2004;554:249-53
   PubMed Web of Science ®Google Scholar
• Collingridge GL, Isaac JT, Wang YT. Receptor trafficking and synaptic plasticity. Nat Rev Neurosci 2004;5:952-62
   PubMed Web of Science ®Google Scholar
• Sommer B, Keinanen K, Verdoorn TA, Flip and flop: a cell-specific functional switch in glutamate-operated channels of the CNS. Science 1990;249:1580-5
   PubMed Web of Science ®Google Scholar
• O'Neill MJ, Bleakman D, Zimmerman DM, Nisenbaum ES. AMPA receptor potentiators for the treatment of CNS disorders. Curr Drug Targets CNS Neurol Disord 2004;3:181-94
   PubMedGoogle Scholar
• O'Neill MJ, Dix S. AMPA receptor potentiators as cognitive enhancers. IDrugs 2007;10:185-92
   PubMedGoogle Scholar
• Zarate CA Jr, Manji HK. The role of AMPA receptor modulation in the treatment of neuropsychiatric diseases. Exp Neurol 2008;211:7-10
   PubMed Web of Science ®Google Scholar
• Hashimoto K. Emerging role of glutamate in the pathophysiology of major depressive disorder. Brain Res Rev 2009;61:105-23
   PubMed Web of Science ®Google Scholar
• Pirotte B, Francotte P, Goffin E, Ring-fused thiadiazines as core structures for the development of potent AMPA receptor potentiators. Curr Med Chem 2010;17:3575-82
   PubMed Web of Science ®Google Scholar
• Ward SE, Harries M. Recent advances in the discovery of selective AMPA receptor positive allosteric modulators. Curr Med Chem 2010;17:3503-13
   PubMed Web of Science ®Google Scholar
• Dicou E, Rangon CM, Guimiot F, Positive allosteric modulators of AMPA receptors are neuroprotective against lesions induced by an NMDA agonist in neonatal mouse brain. Brain Res 2003;970:221-5
   PubMed Web of Science ®Google Scholar
• Alt A, Nisenbaum ES, Bleakman D, Witkin JM. A role for AMPA receptors in mood disorders. Biochem Pharmacol 2006;71:1273-88
   PubMed Web of Science ®Google Scholar
• Goff DC, Leahy L, Berman I, A placebo-controlled pilot study of the ampakine CX516 adxded to clozapine in schizophrenia. J Clin Psychopharmacol 2001;21:484-7
   PubMed Web of Science ®Google Scholar
• Lynch G. AMPA receptor modulators as cognitive enhancers. Curr Opin Pharmacol 2004;4:4-11
   PubMed Web of Science ®Google Scholar
• Sanacora G, Zarate CA, Krystal JH, Manji HK. Targeting the glutamatergic system to develop novel, improved therapeutics for mood disorders. Nat Rev Drug Discov 2008;7:426-37
   PubMed Web of Science ®Google Scholar
• Adler LA, Kroon RA, Stein M, A translational approach to evaluate the efficacy and safety of the novel AMPA receptor positive allosteric modulator Org 26576 in adult attention-deficit/hyperactivity disorder. Biol Psychiatry 2012;72:971-7
   PubMed Web of Science ®Google Scholar
• Siegel GJ, Chauhan NB. Neurotrophic factors in Alzheimer's and Parkinson's disease brain. Brain Res Rev 2000;33:199-227
   PubMed Web of Science ®Google Scholar
• Lauterborn JC, Lynch G, Vanderklish P, Positive modulation of AMPA receptors increases neurotrophin expression by hippocampal and cortical neurons. J Neurosci 2000;20:8-21
   PubMed Web of Science ®Google Scholar
• Lauterborn JC, Truong GS, Baudry M, Chronic elevation of brain-derived neurotrophic factor by ampakines. J Pharmacol Exp Ther 2003;307:297-305
   PubMed Web of Science ®Google Scholar
• Lauterborn JC, Pineda E, Chen LY, Ampakines cause sustained increases in brain-derived neurotrophic factor signaling at excitatory synapses without changes in AMPA receptor subunit expression. Neuroscience 2009;159:283-95
   PubMed Web of Science ®Google Scholar
• Mellor IR. The AMPA receptor as a therapeutic target: current perspectives and emerging possibilities. Fut Med Chem 2010;5:877-91
   Google Scholar
• Morrow JA, Maclean JKF, Jamieson C. Recent advances in positive allosteric modulators of the AMPA receptor. Curr Opin Drug Discov Dev 2006;9:571-9
   PubMedGoogle Scholar
• Francotte P, de Tullio P, Pirotte B. Novel dipyrazoles acting as glutamate modulators. Expert Opin Ther Patents 2007;17:1489-93
   Web of Science ®Google Scholar
• O'Neill MJ, Witkin JM. AMPA receptor potentiators: application for depression and parkinson's disease. Curr Drug Targets 2007;8:603-20
   PubMed Web of Science ®Google Scholar
• Arai AC, Kessler M. Pharmacology of ampakine modulators: from AMPA receptors to synapses and behavior. Curr Drug Targets 2007;583-602
   PubMed Web of Science ®Google Scholar
• Sun MK. The quest for treatment of cognitive impairment: AMPA and mGlu5 receptor modulators. Expert Opin Ther Patents 2008;18:999-1010
   Web of Science ®Google Scholar
• Ward SE, Bax BD, Harries M. Challenges for and current status of research into positive modulators of AMPA receptors. Brit J Pharmacol 2010;160:181-90
   PubMed Web of Science ®Google Scholar
• Grove SJA, Jamieson C, Maclean JKF, Positive allosteric modulators of the alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor. J Med Chem 2010;53:7271-9
   PubMed Web of Science ®Google Scholar
• Clinical trials on CX516 and CX691 (Org 24448). Available from: http://www.clinicaltrials.gov/ct2/results?term=CX516&Search=Search [Last accessed 21 January 2013], http://www.clinicaltrials.gov/ct2/results?term=org+24448&Search=Search [Last accessed 21 January 2013]
   Google Scholar
• Servier Exercises Option to Cortex's AMPAKINE® CX1632, An Innovative Compound in Clinical Development for Alzheimer's Disease. Available from: http://www.businesswire.com/news/home/20111006005361/en/Servier-Exercises-Option-Cortex's-AMPAKINE®-CX1632-Innovative [Last accessed 21 January 2013]
   Google Scholar
• Lipina T, Weiss K, Roder J. The ampakine CX546 restores the prepulse inhibition and latent inhibition deficits in mGluR5-deficient mice. Neuropsychopharmacology 2007;32:745-56
   PubMed Web of Science ®Google Scholar
• Mueller R, Li YX, Hampson A, Benzoxazinones as potent positive allosteric AMPA receptor modulators: part I. Bioorg Med Chem Lett 2001;21:3923-6
   Google Scholar
• Cortex Pharmaceuticals, Inc.; Mueller R, Lee S, O'Hare S, 3-Substituted-[1,2,3]benzotriazinone compounds for enhancing glutamatergic synaptic responses. WO085505; 2008
   Google Scholar
• Cortex Pharmaceuticals, Inc.; Cordi A, Rogers G, Mueller R. 3-Substituted-[1,2,3]-benzotriazinone compound for enhancing glutamatergic synaptic responses. WO085506; 2008
   Google Scholar
• Cortex Pharmaceuticals, Inc.; Mueller R, Street L, Rachwal S, Alisala K. 3-Substituted 1,2,3-triazin-4-one's and 3-substituted 1,3-pyrimidinone's for enhancing glutamatergic synaptic responses. WO038752; 2009
   Google Scholar
• Adler LA, Kroon RA, Stein M, A translational approach to evaluate the efficacy and safety of the novel AMPA receptor positive allosteric modulator Org 26576 in adult attention-deficit/hyperactivity disorder. Biol Psychiatry 2012;72:971-7
   PubMed Web of Science ®Google Scholar
• Mueller R, Rachwal S, Tedder ME, Substituted benzoxazinones as potent positive allosteric AMPA receptor modulators: part II. Bioorg Med Chem Lett 2011;21:3927-30
   PubMed Web of Science ®Google Scholar
• Mueller R, Rachwal S, Varney MA, Benzotriazinone and benzopyrimidinone derivatives as potent positive allosteric AMPA receptor modulators. Bioorg Med Chem Lett 2011;21:7455-9
   PubMed Web of Science ®Google Scholar
• Pirotte B, Fontaine J, Lebrun P. Recent advances in the chemistry of potassium channel openers. Curr Med Chem 1995;2:573-82
   Web of Science ®Google Scholar
• Yamada KA, Rothman SM. Diazoxide blocks glutamate desensitization and prolongs excitatory postsynaptic currents in rat hippocampal neurons. J Physiol 1992;458:409-23
   PubMed Web of Science ®Google Scholar
• Randle JC, Biton C, Lepagnol JM. Allosteric potentiation by diazoxide of AMPA receptor currents and synaptic potentials. Eur J Pharmacol 1993;247:257-65
   PubMed Web of Science ®Google Scholar
• Yamada KA, Tang CM. Benzothiadiazides inhibit rapid glutamate receptor desensitization and enhance glutamatergic synaptic currents. J Neurosci 1993;13:3904-15
   PubMed Web of Science ®Google Scholar
• Bertolino M, Baraldi M, Parenti C, Modulation of AMPA/kainate receptors by analogues of diazoxide and cyclothiazide in thin slices of rat hippocampus. Receptors Channels 1993;1:267-78
   PubMedGoogle Scholar
• Zivkovic I, Thompson DM, Bertolino M, 7-Chloro-3-methyl-3-4-dihydro-2H-1,2,4-benzothiadiazine S,S-dioxide (IDRA 21): a benzothiadiazine derivative that enhances cognition by attenuating DL-alpha-amino-2,3-dihydro-5-methyl-3-oxo-4-isoxazolepropanoic acid (AMPA) receptor desensitization. J Pharmacol Exp Ther 1995;272:300-9
   PubMed Web of Science ®Google Scholar
• Thompson DM, Guidotti A, DiBella M, Costa E. 7-Chloro-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine S,S-dioxide (IDRA 21), a congener of aniracetam, potently abates pharmacologically induced cognitive impairments in patas monkeys. Proc Natl Acad Sci USA 1995;92:7667-71
   PubMed Web of Science ®Google Scholar
• Francotte P, de Tullio P, Goffin E, Design, synthesis, and pharmacology of novel 7-substituted 3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxides as positive allosteric modulators of AMPA receptors. J Med Chem 2007;50:3153-7
   PubMed Web of Science ®Google Scholar
• Pirotte B, Podona T, Diouf O, 4H-1,2,4-Pyridothiadiazine 1,1-dioxides and 2,3-dihydro-4H-1,2,4-pyridothiadiazine 1,1-dioxides chemically related to diazoxide and cyclothiazide as powerful positive allosteric modulators of (R/S)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid receptors: design, synthesis, pharmacology, and structure-activity relationships. J Med Chem 1998;41:2946-59
   PubMed Web of Science ®Google Scholar
• Les Laboratoires Servier. Graindorge E, Francotte P, Boverie S, Novel thiadiazine derivatives useful as AMPA receptor modulators, preparation method, and pharmaceutical compositions containing them. FR2854634; 2004
   Google Scholar
• Phillips D, Sonnenberg J, Arai AC, 5′-Alkyl-benzothiadiazides: a new subgroup of AMPA receptor modulators with improved affinity. Bioorg Med Chem 2002;10:1229-48
   PubMed Web of Science ®Google Scholar
• Krintel C, Frydenvang K, Olsen L, Thermodynamics and structural analysis of positive allosteric modulation of the ionotropic glutamate receptor GluA2. Biochem J 2012;441:173-8
   PubMed Web of Science ®Google Scholar
• Les Laboratoires Servier; Pirotte B, de Tullio P, Boverie S, Novel benzothiadiazine dioxide derivatives useful as AMPA receptor modulators, preparation method, and pharmaceutical compositions containing them. WO040210; 2001
   Google Scholar
• Les Laboratoires Servier; Francotte P, Fraikin P, de Tullio P, Preparation of fluorinated benzothiadiazine derivatives and their use as AMPA receptor modulators. EP1557412; 2005
   Google Scholar
• Francotte P, Goffin E, Fraikin P, New fluorinated 1,2,4-benzothiadiazine 1,1-dioxides: discovery of an orally active cognitive enhancer acting through potentiation of the 2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid receptors. J Med Chem 2010;53:1700-11
   PubMed Web of Science ®Google Scholar
• Les Laboratoires Servier; Francotte P, de Tullio P, Pirotte B, New cycloalkylated benzothiadiazine derivatives, method for preparing them and pharmaceutical compositions containing them. WO004139; 2010
   Google Scholar
• Les Laboratoires Servier; de Tullio P, Pirotte B, Botez I, Novel derivatives of cyclopropylated benzothiadiazines, method for preparing them and pharmaceutical compositions containing them. WO083265; 2011
   Google Scholar
• Les Laboratoires Servier; Francotte P, de Tullio P, Pirotte B, Thiochroman derivatives, method for preparing them and pharmaceutical compositions containing them. WO083264;2011
   Google Scholar
• Les Laboratoires Servier; Cordi A, Desos P, Lestage P, Danober L. Benzothiadiazepine derivatives used as AMPA and NMDA receptor modulators. WO106249; 2010
   Google Scholar
• Les Laboratoires Servier. Cordi A, Desos P, Lestage P, Danober L. Novel derivatives of dihydrobenzoxathiazepines, their preparation process and pharmaceutical compositions containing them. CA2752131; 2012
   Google Scholar
• Universita'del Salento (IT) – Uniwersytet Medyczny W Lublinie (PL). Battisti U, Cannazza G, Puja G, Derivatives of 1,2,4-benzothiadiazine dioxide, their preparation and use as allosteric modulators of the AMPA receptor. EP2457906; 2012
   Google Scholar
• Battisti UM, Jozwiak K, Cannazza G, 5-Arylbenzothiadiazine type compounds as positive allosteric modulators of AMPA/Kainate receptors. ACS Med Chem Lett 2012;3:25-9
   PubMed Web of Science ®Google Scholar
• Glaxo Group Ltd.; Bradley DM, Thewlis KM, Ward SE. Compounds which potentiate glutamate receptor and uses thereof in medicine. WO015828; 2006
   Google Scholar
• Glaxo Group Ltd. Andreotti D, Arista L, Cardullo F, Compounds which potentiate glutamate receptor and uses thereof in medicine. WO/087169; 2006
   Google Scholar
• Glaxo Group Ltd.; Thewlis KM, Ward SE. 4-Phenyl-3-(2-propylsulfonylamino) tetrahydrofuran derivatives which potentiate glutamate receptors and are useful In the treatment of schizophrenia. WO/090840; 2007
   Google Scholar
• Pfizer, Inc.; Estep KG, Fliri AFJ, O'Donnell CJ. Sulfonamides and pharmaceutical compositions thereof. WO120093; 2008
   Google Scholar
• Gouaux JE, Song L, Xie Y, Landry DW. GluR2 receptor modulators. US0270508; 2009
   Google Scholar
• N.V. Organon; Gillespie J, Jamieson C, Maclean JKF, Indane derivatives as ampa receptor modulators. WO147167; 2009
   Google Scholar
• N.V. Organon; Gillen KJ, Gillespie J, Jamieson C, Indane derivatives. WO115952; 2010
   Google Scholar
• Pfizer, Inc.; Estep KG, O'Donnell CJ, Xie L. Tetrahydrofuranyl sulfonamides for use as AMPA modulators in the treatment of CNS disorders. WO041162; 2010
   Google Scholar
• Pfizer, Inc.; Fliri AFJ, Gallaschun RJ, O'Donnell CJ, Heterocyclic sulfonamides, uses and pharmaceutical compositions thereof. WO150192; 2010
   Google Scholar
• Ward SE, Harries M, Aldegheri L, Discovery of N-[(2S)-5-(6-fluoro-3-pyridinyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide, a novel clinical AMPA receptor positive modulator. J Med Chem 2010;53:5801-12
   PubMed Web of Science ®Google Scholar
• Thewlis KM, Aldegheri L, Harries MH, N-substituted pyrrolidines and tetrahydrofurans as novel AMPAR positive modulators. Bioorg Med Chem Lett 2010;20:7116-19
   PubMed Web of Science ®Google Scholar
• O'Donnell CJ. PF-4958242: A novel AMPA positive allosteric modulator (PAM) for the treatment of cognitive deficits associated with schizophrenia (MEDI 27). Division of Medicinal Chemistry 242nd ACS National Meeting, 28 August – 1 September 2011, Denver, CO. Available from: http://www.acsmedchem.org/mediabstractf2011.pdf
   Google Scholar
• Fernandez MC, Castano A, Dominguez E, A novel class of AMPA receptor allosteric modulators. Part 1: design, synthesis, and SAR of 3-aryl-4-cyano-5-substituted-heteroaryl-2-carboxylic acid derivatives. Bioorg Med Chem Lett 2006;16:5057-61
   PubMed Web of Science ®Google Scholar
• Zarrinmayeh H, Tromiczak E, Zimmerman DM, A novel class of positive allosteric modulators of AMPA receptors: design, synthesis, and structure-activity relationships of 3-biphenyl-4-yl-4-cyano-5-ethyl-1-methyl-1H-pyrrole-2-carboxylic acid, LY2059346. Bioorg Med Chem Lett 2006;16:5203-6
   PubMed Web of Science ®Google Scholar
• Glaxo Group Ltd.; Bradley DM, Chan WN, Harrison S, Compounds which potentiate AMPA receptor and uses thereof in medicine. WO122241; 2007
   Google Scholar
• Glaxo Group Ltd.; Chan WN, Harrison S, Hughes OR, Compounds which potentiate AMPA receptor and uses thereof in medicine. WO053448; 2009
   Google Scholar
• Glaxo Group Ltd.; Chan WN, Thewlis KM, Ward SE. Thiazoles which potentiate AMPA receptor and medicinal uses thereof. WO053449; 2009
   Google Scholar
• N.V. Organon; Gillen KJ, Jamieson C, Maclean JKF, Pyrazolealkanamide substituted thiophenes as AMPA potentiators. WO003452; 2008
   Google Scholar
• Organon USA, Inc.; Gallagher MG, Jamieson CC, Lyons AJ, Heterocyclic derivatives. US0131455; 2009
   Google Scholar
• Glaxo Group Ltd.; Bradley DM, Chan WN, Harrison S, Compounds which potentiate AMPA receptor and uses thereof in medicine. WO107539; 2007
   Google Scholar
• Glaxo Group Ltd.; Bradley DM, Chan WN, Thewlis KM, Ward SE. Compounds which potentiate AMPA receptor and uses thereof in medicine. WO053031; 2008
   Google Scholar
• Glaxo Group Ltd.; Bertheleme N, Bradley DM, Cardullo F, Compounds which potentiate AMPA receptor and uses thereof in medicine. WO113795; 2008
   Google Scholar
• Glaxo Group Ltd.; Bradley DM, Chan WN, Ward SE. Compounds which potentiate AMPA receptor and uses thereof in medicine. WO148836; 2008
   Google Scholar
• Takeda Pharmaceutical Co. Ltd.; Mochizuki M, Imaeda T. Heterocyclic compound. WO140339; 2010
   Google Scholar
• Jamieson C, Basten S, Campbell RA, A novel series of positive modulators of the AMPA receptor: discovery and structure based hit-to-lead studies. Bioorg Med Chem Lett 2010;20:5753-6
   PubMed Web of Science ®Google Scholar
• Jamieson C, Campbell RA, Cumming IA, A novel series of positive modulators of the AMPA receptor: structure-based lead optimization. Bioorg Med Chem Lett 2010;20:6072-5
   PubMed Web of Science ®Google Scholar
• Jamieson C, Maclean JK, Brown CI, Structure based evolution of a novel series of positive modulators of the AMPA receptor. Bioorg Med Chem Lett 2011;21:805-11
   PubMed Web of Science ®Google Scholar
• Ward SE, Harries M, Aldegheri L, Integration of lead optimization with crystallography for a membrane-bound ion channel target: discovery of a new class of AMPA receptor positive allosteric modulators. J Med Chem 2011;54:78-94
   PubMed Web of Science ®Google Scholar