Development of thiophenic analogues of benzothiadiazine dioxides as new powerful potentiators of 2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid (AMPA) receptors

Journal of Medicinal Chemistry

Volumn 56, Issue 20, 2013, Pages 7838-7850

  Francotte, Pierre ^a   Goffin, Eric ^a   Fraikin, Pierre ^a   Graindorge, E ^a   Lestage, Pierre ^b   Danober, Laurence ^b   Challal, Sylvie ^b   Rogez, Nathalie ^b   Nosjean, Olivier ^b   Caignard, Daniel Henri ^b   Pirotte, Bernard ^a   De Tullio, Pascal ^a  

^a UNIVERSITY OF LIÈGE   (Belgium)

^b INSTITUT DE RECHERCHES SERVIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

5,7 DICHLORO 3,4 DIHYDRO 2H THIENO[3,4 E] 1,2,4 THIADIAZINE 1,1, DIOXIDE; 5,7 DICHLORO 4 (2 FLUOROETHYL) 3,4 DIHYDRO 2H THIENO[3,4 E] 1,2,4 THIADIAZINE 1,1, DIOXIDE; 5,7 DICHLORO 4 (2 FLUOROETHYL) 4H THIENO[3,4 E] 1,2,4 THIADIAZINE 1,1 DIOXIDE; 5,7 DICHLORO 4 (2,2 DIFLUOROETHYL) 3,4 DIHYDRO 2H THIENO[3,4 E] 1,2,4 THIADIAZINE 1,1, DIOXIDE; 5,7 DICHLORO 4 (2,2 DIFLUOROETHYL) 4H THIENO[3,4 E] 1,2,4 THIADIAZINE 1,1 DIOXIDE; 5,7 DICHLORO 4 ETHYL 3,4 DIHYDRO 2H THIENO[3,4 E] 1,2,4 THIADIAZINE 1,1, DIOXIDE; 5,7 DICHLORO 4 ETHYL 4H THIENO[3,4 E] 1,2,4 THIADIAZINE 1,1 DIOXIDE; 5,7 DICHLORO 4 METHYL 3,4 DIHYDRO 2H THIENO[3,4 E] 1,2,4 THIADIAZINE 1,1, DIOXIDE; 5,7 DICHLORO 4 METHYL 4H THIENO[3,4 E] 1,2,4 THIADIAZINE 1,1 DIOXIDE; 5,7 DICHLORO 4 PROPYL 3,4 DIHYDRO 2H THIENO[3,4 E] 1,2,4 THIADIAZINE 1,1, DIOXIDE; 5,7 DICHLORO 4 PROPYL 4H THIENO[3,4 E] 1,2,4 THIADIAZINE 1,1 DIOXIDE; 5,7 DICHLORO 4H THIENO[3,4 E] 1,2,4 THIADIAZINE 1,1 DIOXIDE; 6 CHLORO 4 (2 FLUOROETHYL) 4H THIENO[3,2 E] 1,2,4 THIADIAZINE 1,1 DIOXIDE; 6 CHLORO 4 (FLUOROMETHYL) 4H THIENO[3,2 E] 1,2,4 THIADIAZINE 1,1 DIOXIDE; 6 CHLORO 4 ETHYL 3,4 DIHYDRO 2H THIENO[2,3 E] 1,2,4 THIADIAZINE 1,1 DIOXIDE; 6 CHLORO 4 ETHYL 4H THIENO[2,3 E] 1,2,4 THIADIAZINE 1,1 DIOXIDE; 6 CHLORO 4 ETHYL 4H THIENO[3,2 E] 1,2,4 THIADIAZINE 1,1 DIOXIDE; 6 CHLORO 4 ISOPROPYL 4H THIENO[3,2 E] 1,2,4 THIADIAZINE 1,1 DIOXIDE; 6 CHLORO 4 METHYL 4H THIENO[3,2 E] 1,2,4 THIADIAZINE 1,1 DIOXIDE; 6 CHLORO 4 PROPYL 4H THIENO[3,2 E] 1,2,4 THIADIAZINE 1,1 DIOXIDE; 6 CHLORO 4H THIENO[3,2 E] 1,2,4 THIADIAZINE 1,1 DIOXIDE; ALPHA AMINO 3 HYDROXY 5 METHYL 4 ISOXAZOLEPROPIONIC ACID; AMPA RECEPTOR; AMPA RECEPTOR AGONIST; BENZOTHIADIAZINE DERIVATIVE; NORADRENALIN; PYRIDINE; SULFUR; THIOPHENE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ACUTE TOXICITY; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; APATHY; ARTICLE; BLOOD BRAIN BARRIER; COGNITION; CONTROLLED STUDY; CONVULSION; DOSE RESPONSE; DRUG BRAIN LEVEL; DRUG EFFICACY; DRUG MEGADOSE; DRUG METABOLISM; DRUG POTENCY; DRUG SAFETY; DRUG STABILITY; EMBRYO; EXCITATORY POSTSYNAPTIC POTENTIAL; FEMALE; HIPPOCAMPUS; HYPOTHERMIA; IN VIVO STUDY; LONG TERM POTENTIATION; LOW DRUG DOSE; MALE; MOUSE; NONHUMAN; NORADRENALIN RELEASE; RAT; RECOGNITION; STRUCTURE ACTIVITY RELATION;

ALPHA-AMINO-3-HYDROXY-5-METHYL-4-ISOXAZOLEPROPIONIC ACID; ANIMALS; BENZOTHIADIAZINES; CELLS, CULTURED; COGNITION; CYCLIC S-OXIDES; DIAZOXIDE; DRUG DESIGN; EXCITATORY AMINO ACID AGONISTS; EXCITATORY POSTSYNAPTIC POTENTIALS; FEMALE; HIPPOCAMPUS; LONG-TERM POTENTIATION; MEMBRANE POTENTIALS; MICE; MODELS, CHEMICAL; MOLECULAR STRUCTURE; NOREPINEPHRINE; OOCYTES; RATS; RECEPTORS, AMPA; THIADIAZINES; THIOPHENES; XENOPUS LAEVIS;

EID: 84886545732     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm400676g     Document Type: Article

References (31)

1. Yamada, K. A.; Tang, C. M. Benzothiadiazides inhibit rapid glutamate receptor desensitization and enhance glutamatergic synaptic currents J. Neurosci. 1993, 13, 3904-3915
2. Yamada, K. A.; Rothman, S. M. Diazoxide blocks glutamate desensitization and prolongs excitatory postsynaptic currents in rat hippocampal neurons J. Physiol. 1992, 458, 409-423
3. Bertolino, M.; Baraldi, M.; Parenti, C.; Braghiroli, D.; DiBella, M.; Vicini, S.; Costa, E. Modulation of AMPA/kainate receptors by analogues of diazoxide and cyclothiazide in thin slices of rat hippocampus Recept. Channels 1993, 1, 267-278
4. Bernard, K.; Danober, L.; Thomas, J. Y.; Lebrun, C.; Munoz, C.; Cordi, A.; Desos, P.; Lestage, P.; Morain, P. DRUG FOCUS: S 18986: a positive allosteric modulator of AMPA-type glutamate receptors pharmacological profile of a novel cognitive enhancer CNS Neurosci. Ther. 2010, 16, e193-e212
5. Staubli, U.; Rogers, G.; Lynch, G. Facilitation of glutamate receptors enhances memory Proc. Natl. Acad. Sci. U. S. A. 1994, 91, 777-781
6. Black, M. D. Therapeutic potential of positive AMPA modulators and their relationship to AMPA receptor subunits. A review of preclinical data Psychopharmacology (Berlin) 2005, 179, 154-163
7. Francotte, P.; de Tullio, P.; Fraikin, P.; Counerotte, S.; Goffin, E.; Pirotte, B. In search of novel AMPA potentiators Recent Pat. CNS Drug Discovery 2006, 1, 239-246
8. Krintel, C.; Frydenvang, K.; Olsen, L.; Kristensen, M. T.; de Barrios, O.; Naur, P.; Francotte, P.; Pirotte, B.; Gajhede, M.; Kastrup, J. S. Thermodynamics and structural analysis of positive allosteric modulation of the ionotropic glutamate receptor GluA2 Biochem. J. 2012, 441, 173-178
9. Goff, D. C.; Leahy, L.; Berman, I.; Posever, T.; Herz, L.; Leon, A. C.; Johnson, S. A.; Lynch, G. A placebo-controlled pilot study of the ampakine CX516 added to clozapine in schizophrenia J. Clin. Psychopharmacol. 2001, 21, 484-487
10. O'Neill, M. J.; Witkin, J. M. AMPA receptor potentiators: application for depression and Parkinson's disease Curr. Drug Targets 2007, 8, 603-620
11. Alt, A.; Nisenbaum, E. S.; Bleakman, D.; Witkin, J. M. A role for AMPA receptors in mood disorders Biochem. Pharmacol. 2006, 71, 1273-1288
12. Braghiroli, D.; Puia, G.; Cannazza, G.; Tait, A.; Parenti, C.; Losi, G.; Baraldi, M. Synthesis of 3,4-dihydro-2 H -1,2,4-benzo-thiadiazine 1,1-dioxide derivatives as potential allosteric modulators of AMPA/kainate receptors J. Med. Chem. 2002, 45, 2355-2357
13. Pirotte, B.; Francotte, P.; Goffin, E.; Fraikin, P.; Danober, L.; Lesur, B.; Botez, I.; Caignard, D. H.; Lestage, P.; de Tullio, P. Ring-fused thiadiazines as core structures for the development of potent AMPA receptor potentiators Curr. Med. Chem. 2010, 17, 3575-3582
14. Phillips, D.; Sonnenberg, J.; Arai, A. C.; Vaswani, R.; Krutzik, P. O.; Kleisli, T.; Kessler, M.; Granger, R.; Lynch, G.; Richard Chamberlin, A. 5'-Alkyl-benzothiadiazides: a new subgroup of AMPA receptor modulators with improved affinity Bioorg. Med. Chem. 2002, 10, 1229-1248
15. 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. 4 H -1,2,4-Pyridothiadiazine 1,1-dioxides and 2,3-dihydro-4 H -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, 2946-2959
16. Francotte, P.; 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-2 H -1,2,4-benzothiadiazine 1,1-dioxides as positive allosteric modulators of AMPA receptors J. Med. Chem. 2007, 50, 3153-3157
17. 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 generation of pyridothiadiazine 1,1-dioxides acting as AMPA potentiators Bioorg. Med. Chem. 2008, 16, 9948-9956
18. 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 cognitive enhancer acting through potentiation of the 2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid receptors J. Med. Chem. 2010, 53, 1700-1711
19. Mourlevat, S.; Galizzi, J. P.; Guigal-Stephan, N.; Courtade-Gaiani, S.; Rolland-Valognes, G.; Rodriguez, M.; Barbet, F.; Bourrier, C.; Catesson, S.; Chomel, A.; Danober, L.; Villain, N.; Caignard, D. H.; Pirotte, B.; Lestage, P.; Lockhart, B. P. Molecular characterization of the AMPA-receptor potentiator S70340 in rat primary cortical culture: whole-genome expression profiling Neurosci. Res. 2011, 70, 349-360
20. Lima, L. M.; Barreiro, E. J. Bioisosterism: a useful strategy for molecular modification and drug design Curr. Med. Chem. 2005, 12, 23-49
21. Nielsen, F. E.; Ebdrup, S.; Jensen, A. F.; Ynddal, L.; Bodvarsdottir, T. B.; Stidsen, C.; Worsaae, A.; Boonen, H. C.; Arkhammar, P. O.; Fremming, T.; Wahl, P.; Korno, H. T.; Hansen, J. B. New 3-alkylamino-4 H -thieno-1,2,4- thiadiazine 1,1-dioxide derivatives activate ATP-sensitive potassium channels of pancreatic beta cells J. Med. Chem. 2006, 49, 4127-4139
22. Topliss, J. G. Method of treating hypertension with thieno[1,2,4] thiadiazines. U.S. Patent US3733409 A, May 15, 1973.
23. Arranz, E.; Diaz, J. A.; Vega, S.; Campos-Toimil, M.; Orallo, F.; Cardelus, I.; Llenas, J.; Fernandez, A. G. Synthesis and pharmacological evaluation of 2, 3-dihydro-3-oxo-4 H -thieno[3,4- e ][1,2,4]thiadiazine 1,1-dioxides as voltage-dependent calcium channel blockers Eur. J. Med. Chem. 2000, 35, 751-759
24. Nielsen, F. E.; Bodvarsdottir, T. B.; Worsaae, A.; MacKay, P.; Stidsen, C. E.; Boonen, H. C.; Pridal, L.; Arkhammar, P. O.; Wahl, P.; Ynddal, L.; Junager, F.; Dragsted, N.; Tagmose, T. M.; Mogensen, J. P.; Koch, A.; Treppendahl, S. P.; Hansen, J. B. 6-Chloro-3-alkylamino-4 H -thieno[3,2- e ]-1,2,4-thiadiazine 1,1-dioxide derivatives potently and selectively activate ATP sensitive potassium channels of pancreatic beta-cells J. Med. Chem. 2002, 45, 4171-4187
25. Qi, J.; Wang, Y.; Jiang, M.; Warren, P.; Chen, G. Cyclothiazide induces robust epileptiform activity in rat hippocampal neurons both in vitro and in vivo J. Physiol. 2006, 571, 605-618
26. Arai, A. C.; Kessler, M. Pharmacology of ampakine modulators: from AMPA receptors to synapses and behavior Curr. Drug Targets 2007, 8, 583-602
27. Ohta, K.; Araki, N.; Shibata, M.; Komatsumoto, S.; Shimazu, K.; Fukuuchi, Y. Presynaptic ionotropic glutamate receptors modulate in vivo release and metabolism of striatal dopamine, noradrenaline, and 5-hydroxytryptamine: involvement of both NMDA and AMPA/kainate subtypes Neurosci. Res. 1994, 21, 83-89
28. Cowen, M. S.; Beart, P. M. Cyclothiazide and AMPA receptor desensitization: analyses from studies of AMPA-induced release of [3H]-noradrenaline from hippocampal slices Br. J. Pharmacol. 1998, 123, 473-480
29. 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)-AMPA-mediated [3H]noradrenaline release from rat hippocampal and frontal cortex slices Eur. J. Pharmacol. 2000, 401, 145-53
30. Ennaceur, A.; Delacour, J. A new one-trial test for neurobiological studies of memory in rats. 1: Behavioral data Behav. Brain Res. 1988, 31, 47-59
31. Cymerman-Craig, J.; Willis, D.; Rubbo, S. D.; Edgar, J. Mode of action of isonicotinic hydrazide Nature 1955, 176, 34-35