Ring-fused thiadiazines as core structures for the development of potent AMPA receptor potentiators

Current Medicinal Chemistry

Volumn 17, Issue 30, 2010, Pages 3575-3582

  Pirotte, B ^a   Francotte, P ^a   Goffin, E ^a   Fraikin, P ^a   Danober, L ^b   Lesur, B ^b   Botez, I ^b   Caignard, D H ^b   Lestage, P ^b   de Tullio, P D ^a  

^a UNIVERSITY OF LIÈGE   (Belgium)

^b INSTITUT DE RECHERCHES SERVIER   (France)

Author keywords

AMPA receptor potentiators; Benzothiadiazines; Neurological disorders; Positive allosteric modulators; Pyridothiadiazines; Thienothiadiazines

Indexed keywords

2,3 DIHYDRO 3,4 CYCLOPENTANO 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; 7 CHLORO 3,4 DIHYDRO 3 METHYL 2H 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; AMPA RECEPTOR; AMPA RECEPTOR AGONIST; CYCLOTHIAZIDE; DIAZOXIDE; THIADIAZINE DERIVATIVE;

ALZHEIMER DISEASE; ARTICLE; CENTRAL NERVOUS SYSTEM; DEPRESSION; DRUG STRUCTURE; HUMAN; LEARNING DISORDER; LONG TERM POTENTIATION; MEMORY DISORDER; NEUROLOGIC DISEASE; NEUROTRANSMISSION; NONHUMAN; PARKINSON DISEASE; SCHIZOPHRENIA;

ALLOSTERIC REGULATION; HUMANS; NERVOUS SYSTEM DISEASES; RECEPTORS, AMPA; THIADIAZINES;

EID: 77957948842     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: 10.2174/092986710792927859     Document Type: Article

References (59)

1. Francotte, P.; de Tullio, P.; Fraikin, P.; Counerotte, S.; Goffin, E., Pirotte, B. In search of novel AMPA potentiators. Recent Pat. CNSDrug Discov., 2006, 1, 239-246.
2. Armstrong, N.;Gouaux, E. Mechanisms for activation and antago-nism of an AMPA-sensitive glutamate receptor: crystal structuresof the GluR2 ligand binding core. Neuron, 2000, 28, 165-181.
3. Mansour, M., Nagarajan, N., Nehring, R.B., Clements, J.D., Rosenmund, C. Heteromeric AMPA receptors assemble with a pre-ferred subunit stoichiometry and spatial arrangement. Neuron,2001, 32, 841-853.
4. Robert, A.; Irizarry, S.N.; Hughes, T.E.; Howe, J.R. Subunit inter-actions and AMPA receptor desensitization. J. Neurosci., 2001, 21,5574-5586.
5. Greger, I.H.; Esteban, J.A. AMPA receptor biogenesis and traffick-ing. Curr. Opin. Neurobiol. 2007, 17, 289-297.
6. Sommer, B. Keinänen, K., Verdoorn T.A. Wisden W. Bur-nashev N. Herb A. hler M. Takagi T. Sakmann B. Seeburg P.H. Flip and flop: a cell-specific functional switch in glu-tamate-operated channels of the CNS. Science, 1990, 249, 1580-1585.
7. O'Neill, M.J.; Bleakman, D.; Zimmerman, D.M.; Nisenbaum, E.S. AMPA receptor potentiators for the treatment of CNS disorders.Curr. Drug Targets CNS Neurol. Disord., 2004, 3, 181-194.
8. O'Neill, M.J.; Dix, S. AMPA receptor potentiators as cognitiveenhancers. IDrugs, 2007, 10, 185-192.
9. Zarate, C.A. Jr.; Manji, H.K. The role of AMPA receptor modula-tion in the treatment of neuropsychiatric diseases. Exp. Neurol.,2008, 211, 7-10.
10. Hashimoto, K. Emerging role of glutamate in the pathophysiologyof major depressive disorder. Brain Res. Rev., 2009, 61, 105-123.
11. Alt, A.; Nisenbaum, E.S.; Bleakman, D.; Witkin, J.M. A role forAMPA receptors in mood disorders. Biochem. Pharmacol., 2006,71, 1273-1288.
12. Goff, D.C.; Leahy, L.; Berman, I.; Posever, T.; Herz, L.; Leon, A.C.; Johnson, S.A.; Lynch, G. A placebo-controlled pilot study ofthe ampakine CX516 added to clozapine in schizophrenia. J. Clin.Psychopharmacol., 2001, 21, 484-487.
13. Lynch, G. AMPA receptor modulators as cognitive enhancers.Curr. Opin. Pharmacol., 2004, 4, 4-11.
14. Lauterborn, J.C.; Lynch, G.; Vanderklish, P.; Arai, A.; Gall, C.M. Positive modulation of AMPA receptors increases neurotrophinexpression by hippocampal and cortical neurons. J. Neurosci.,2000, 20, 8-21.
15. Lauterborn, J.C.; Truong, G.S.; Baudry, M.; Bi, X.; Lynch, G.; Gall, C.M. Chronic elevation of brain-derived neurotrophic factorby ampakines. J. Pharmacol. Exp. Ther., 2003, 307, 297-305.
16. Lauterborn, J.C.; Pineda, E.; Chen, L.Y.; Ramirez, E.A.; Lynch, G.; Gall, C.M. Ampakines cause sustained increases in brain-derivedneurotrophic factor signaling at excitatory synapses withoutchanges in AMPA receptor subunit expression. Neuroscience,2009, 159, 283-295.
17. Pirotte, B.; Fontaine, J.; Lebrun, P. Recent advances in the chemistryof potassium channel openers. Curr. Med. Chem., 1995, 2, 573-582.
18. Yamada, K.A.; Rothman, S.M. Diazoxide blocks glutamate desensitizationand prolongs excitatory postsynaptic currents in rat hippocampalneurons. J. Physiol., 1992, 458, 409-423.
19. Randle, J.C.; Biton, C.; Lepagnol, J.M. Allosteric potentiation bydiazoxide of AMPA receptor currents and synaptic potentials. Eur.J. Pharmacol., 1993, 247, 257-265.
20. Yamada, K.A.; Tang, C.M. Benzothiadiazides inhibit rapid glutamatereceptor desensitization and enhance glutamatergic synapticcurrents. J. Neurosci., 1993, 13, 3904-15.
21. Bertolino, M.; Baraldi, M.; Parenti, C.; Braghiroli, D.; DiBella, M.; Vicini, S.; Costa, E. Modulation of AMPA/kainate receptors by analoguesof diazoxide and cyclothiazide in thin slices of rat hippocampus.Receptors Channels, 1993, 1, 267-278.
22. Aloup, J.-C.; Audiau, F.; Damour, D.; Jimonet, P.; Mignani, S. Preparation of 3,4-dihydro-2H-1,2,4-benzothiadiazine-1,1-dioxide-3-carboxylates as AMPA and NMDA receptor antagonists. WO9321170, 1993.
23. Leeson, P.D.; Baker, R.; Carling R.W.; Curtis, N.R.; Moore, K.W.; Williams, B.J.; Foster, A.C.; Donald, A.E.; Kemp, J.A.; Marshall, G.R. Kynurenic acid derivatives. Structure-activity relationshipsfor excitatory amino acid antagonism and identification of potentand selective antagonists at the glycine site on the N-methyl-Daspartatereceptor. J. Med. Chem., 1991, 34, 1243-1252.
24. Cordi, A.A.; Serkiz, B.; Hennig, P.; Mahieu, J.-P.; Bobichon, C.; deNanteuil, G.; Lepagnol, J.M. Identification and characterisation ofthe isomers of cyclothiazide responsible for potentiating AMPAcurrent. Bioorg. Med. Chem. Lett., 1994, 4, 1957-1960.
25. Sun, Y.; Olson, R.; Horning, M.; Armstrong, N.; Mayer, M.; Gouaux, E. Mechanism of glutamate receptor desensitization. Nature,2002, 417, 245-253.
26. Zivkovic, I.; Thompson, D.M.; Bertolino, M.; Uzunov, D.; DiBella, M.; Costa, E.; Guidotti, A. 7-Chloro-3-methyl-3-4-dihydro-2H-1,2,4 benzothiadiazine S,S-dioxide (IDRA 21): a benzothiadiazinederivative 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, 272,300-309.
27. Uzunov D.P.; Zivkovich, I.; Pirkle, W.H., Costa, E.; Guidotti A.X. Enantiomeric resolution with a new chiral stationary phase of 7-chloro-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine S,S-dioxide,a cognition-enhancing benzothiadiazine derivative. J.Pharm. Sci., 1995, 84, 937-942.
28. Costa, E.; Guidotti, A.; Baraldi, M.; Bertolino, M.; Di Bella, M.; Vivini, S. A method of treating learning and memory disorders usingbenzothiadiazides as nootropic agents. WO 9515759, 1995.
29. Cannazza, G.; Braghiroli, D.; Baraldi, M.; Parenti, C. Chiral resolutionof the enantiomers of 7-chloro-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide using high-performance liquid chromatographyon cellulose-based chiral stationary phases. J. Pharm.Biomed. Anal., 2000, 23, 117-125.
30. Cannazza, G.; Carrozzo, M.M.; Braghiroli, D.; Parenti, C. Enantiomerizationand hydrolysis of (+/-)-7-chloro-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide by stopped-flowmultidimensional high-performance liquid chromatography. J.Chromatogr. A., 2008, 1212, 41-47.
31. Thompson D.M.; Guidotti, A.; DiBella, M.; Costa, E. 7-Chloro-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine S,S-dioxide (IDRA21), a congener of aniracetam, potently abates pharmacologicallyinduced cognitive impairments in patas monkeys. Proc. Natl. Acad.Sci. U. S. A., 1995, 92, 7667-7671.
32. Pirotte, B.; de Tullio, P.; Masereel, B.; Delarge, J.; Lepagnol, J.; Renard, P.; New pyridothiadiazines, processes for their preparation,and pharmaceutical compositions containing them. EP618209, 1994.
33. Pirotte, B.; de Tullio, P.; Boverie, S.; Kempen, I.; Lestage, P. Novel benzothiadiazine dioxide derivatives useful as AMPA receptormodulators, preparation method, and pharmaceutical compositionscontaining them. WO 2001040210, 2001.
34. Cordi, A.; Spedding, M.; Serkiz, B.; Lepagnol, J.; Desos, P.; Morain, P. Preparation of (3aS)-5,5-dioxo-2,3,3a,4-tetrahydro-1Hpyrrolo[2,1-c][1,2,4]benzothiadiazine AMPA receptor agonist. EP692484, 1996.
35. Desos, P.; Serkiz, B.; Morain, P.; Lepagnol, J.; Cordi, A. Enantioselectivesynthesis of a pyrrolo-benzothiadiazine derivative S18986, a new AMPA receptor positive modulator. Bioorg. Med.Chem. Lett., 1996, 6, 3003-3008.
36. Lockhart, B.; Iop, F.; Closier, M.; Lestage, P. (S)-2,3-dihydro-[3,4]cyclopentano-1,2,4-benzothiadiazine-1,1-dioxide: (S18986-1)a positive modulator of AMPA receptors enhances (S)-AMPAmediated[3H]noradrenaline release from rat hippocampal andfrontal cortex slices. Eur. J. Pharmacol., 2000, 401, 145-153.
37. Lebrun, C.; Pillière, E.; Lestage, P. Effects of S 18986-1, a novelcognitive enhancer, on memory performances in an object recognitiontask in rats. Eur. J. Pharmacol., 2000, 401, 205-212.
38. Rosi, S.; Giovannini, M.G.; Lestage, P.J.; Muñoz, C.; Corte, L.D.; Pepeu, G. S18986, a positive modulator of AMPA receptors withcognition-enhancing properties, increases ACh release in the hippocampusof young and aged rat. Neurosci. Lett., 2004, 361, 120-123.
39. Lockhart, B.P.; Rodriguez, M.; Mourlevat, S.; Peron, P.; Catesson, S.; Villain, N.; Galizzi J.P., Boutin, J.A.; Lestage, P. S18986: a positive modulator of AMPA-receptors enhances (S)-AMPA-mediated BDNF mRNA and protein expression in rat primarycortical neuronal cultures. Eur. J. Pharmacol., 2007, 561, 23-31.
40. Kelly, S.J.; Bernard, K.; Muñoz, C.; Lawrence, R.C.; Thacker, J.; Grillo, C.A.; Piroli, G.G.; Reagan, L.P. Effects of the AMPA receptormodulator S 18986 on measures of cognition and oxidativestress in aged rats. Psychopharmacology (Berl)., 2009, 202, 225-235.
41. Pirotte, B.; Podona, T.; Diouf, O.; de Tullio, P.; Lebrun, P.; Dupont, L.; Somers, F.; Delarge, J.; Morain, P.; Lestage, P.; Lepagnol, J.; Spedding, M. 4H-1,2,4-Pyridothiadiazine 1,1-dioxides and 2,3-dihydro-4H-1,2,4-pyridothiadiazine 1,1-dioxideschemically related to diazoxide and cyclothiazide as powerful positiveallosteric 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, 2946-2959.
42. Francotte, P.; de Tullio, P.; Podona, T.; Diouf, O.; Fraikin, P.; Lestage, P.; Danober, L.; Thomas, J.Y.; Caignard, D.H.; Pirotte, B. Synthesis and pharmacological evaluation of a second generationof pyridothiadiazine 1,1-dioxides acting as AMPA potentiators.Bioorg. Med. Chem., 2008, 16, 9948-9956.
43. Lynch, G.; Chamberlin, R.; Kessler, M.; Granger, R.; Sonnenberg, J.; Arai, A. Preparation of benzothiadiazole dioxide derivatives asallosteric up-modulators of the AMPA receptor. WO 9812185,1998.
44. Phillips, D.; Sonnenberg, J.; Arai, A.C.; Vaswani, R.; Krutzik, P.O.; Kleisli, T.; Kessler, M.; Granger, R.; Lynch, G.; Chamberlin, A.R. 5'-alkyl-benzothiadiazides: a new subgroup of AMPA receptormodulators with improved affinity. Bioorg. Med. Chem., 2002,10, 1229-1248.
45. Gouliaev, A.H.; Larsen, M.; Varming, T.; Mathiesen, C.; Johansen, T. H.; Scheel-Kruger, J.; Olsen, G.M.; Nielsen, E.O. Preparation ofbenzothiadiazines, quinazolines, and other aryl-fused heterocyclesas positive AMPA-receptor modulators for treatment of memoryand learning disorders. WO 9942456, 1999.
46. Braghiroli, D.; Puia, G.; Cannazza, G.; Tait, A.; Parenti, C.; Losi, G.; Baraldi, M. Synthesis of 3,4-dihydro-2H-1,2,4-benzothiadiazine1,1-dioxide derivatives as potential allosteric modula tors of AMPA/kainate receptors. J. Med. Chem., 2002, 45, 2355-2357.
47. Cordi, A.; Desos, P.; Lefoulon, F.; Lestage, P. Preparation of pyrrolo[2,1-c][1,2,4]benzothiadiazines as AMPA receptor agonists. EP1176148, 2002.
48. Cordi, A.; Desos, P.; Lestage, P. New hydroxy and acyloxy derivativesof benzothiazine and benzothiadiazine, process for theirpreparation, and pharmaceutical compositions containing them asAMPA receptor modulators. FR 2833950, 2003.
49. Cordi, A.; Desos, P.; Lestage, P. New aryl carbonate, thiocarbonate,and dithiocarbonate derivatives of benzothiazine and benzothiadiazine,process for their preparation, and pharmaceuticalcompositions containing them as AMPA receptor modulators. FR2833955, 2003.
50. Desos, P.; Cordy, A.; Lestage, P. Derivatives of benzothiazine andbenzothiadiazine, process for their preparation and pharmaceuticalcompositions containing them as AMPA receptor modulators. EP1486502, 2004.
51. Desos, P.; Cordy, A.; Lestage, P. Derivatives of benzothiazine andbenzothiadiazine, process for their preparation, and pharmaceuticalcompositions containing them as AMPA receptor modulators. EP1486503, 2004.
52. Desos, P.; Cordy, A.; Lestage, P.; Danober, L. Derivatives of benzothiazineand benzothiadiazine, process for their preparation, andpharmaceutical compositions containing them as AMPA receptormodulators. EP 1669072, 2006.
53. Cordi, A.; Desos, P.; Lestage, P. New aryloxy- and heteroaryloxysubstitutedderivatives of benzothiazine and benzothiadiazine,process for their preparation, and pharmaceutical compositions containing them as AMPA receptor modulators. FR 2833956,2003.
54. Graindorge, E.; Francotte, P.; Boverie, S.; de Tullio, P.; Pirotte, B.; Lestage, P.; Danober, L.; Renard, P.; Caignard, D.H. Novel thiadiazinederivatives useful as AMPA receptor modulators, preparationmethod, and pharmaceutical compositions containing them. FR2854634, 2004.
55. Francotte, P.; de Tullio, P.; Goffin, E.; Dintilhac, G.; Graindorge, E.; Fraikin, P.; Lestage, P.; Danober, L.; Thomas, J.Y.; Caignard, D.H.; Pirotte, B. Design, synthesis, and pharmacology of novel 7-substituted 3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxides aspositive allosteric modulators of AMPA receptors. J. Med. Chem.,2007, 50, 3153-3157.
56. Francotte, P.; Fraikin, P.; de Tullio, P.; Pirotte, B.; Lestage, P.; Danober, L.; Caignard, D.H.; Renard, P. Preparation of fluorinatedbenzothiadiazine derivatives and their use as AMPA receptormodulators. EP 1557412, 2005.
57. Francotte, P.; Goffin, E.; Fraikin, P.; Lestage, P.; Van Heugen, J.-C.; Gillotin, F.; Danober, L.; Thomas, J.-Y.; Chiap, P.; Caignard, D.-H.; Pirotte, B.; de Tullio, P. New fluorinated 1,2,4-benzothiadiazine 1,1-dioxides: discovery of an orally active cognitiveenhancer acting through potentiation of the 2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid receptors. J. Med.Chem., 2010, 53, 1700-1711.
58. Desos, P.; Cordi, A.; Lestage, P. Preparation of benzothiadiazineswhich are AMPA receptor modulators. US 2006094713, 2006.
59. Desos, P.; Cordi, A.; Lestage, P. Preparation of benzothiadiazinecompounds for treating or preventing disorders associated withAMPA flux. US 2006094712, 2006.