Synthesis and structure-activity relationships of 4,10-dihydro-4-oxo-4H-imidazo [1,2-a]indeno [1,2-e]pyrazine derivatives: Highly potent and selective AMPA receptor antagonists with in vivo activity

Mini-Reviews in Medicinal Chemistry

Volumn 4, Issue 2, 2004, Pages 123-140

  Stutzmann, Jean Marie ^a   Vuilhorgne, Marc ^a   Mignani, Serge ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

10 SPIROIMIDAZO[1,2 A]INDENO[1,2 E]PYRAZIN 4 ONE DERIVATIVE; 4 OXO 10 IMIDAZO[1,2 A]INDENO[1,2 E]PYRAZIN 2 CARBOXYLIC ACIDE DERIVATIVE; 4,10 DIHYDRO 4 OXO 4H IMIDAZO[1,2 A]INDENO[1,2 E]PYRAZINE DERIVATIVE; 6 (1 IMIDAZOLYL) 7 NITRO 2,3 QUINOXALINEDIONE; 6 NITRO 7 SULFAMOYLBENZO[F]QUINOXALINE 2,3 DIONE; 8 METHYLUREIDO 4 OXO IMIDAZO[1,2 A]INDENO[1,2 E]PYRAZINE DERIVATIVE; 9 CARBOXYMETHYL 5H,10H IMIDAZO[1,2 A]INDENO[1,2 E] PYRAZIN 4 ONE PHOSPHONIC ACID; 9 CARBOXYMETHYLIMIDAZOINDENOPYRAZIN 4 ONE 2 CARBOXYLIC ACID; [1,2,3,4 TETRAHYDRO 7 (1H IMIDAZOL 1 YL) 6 NITRO 2,3 DIOXO 1 QUINOXALINYL]ACETIC ACID; ALPHA AMINO 3 HYDROXY 5 METHYL 4 ISOXAZOLEPROPIONIC ACID; AMPA RECEPTOR; AMPA RECEPTOR ANTAGONIST; ANTICONVULSIVE AGENT; DECAHYDRO 6 [2 (1H TETRAZOL 5 YL)ETHYL] 3 ISOQUINOLINECARBOXYLIC ACID; GLUTAMATE RECEPTOR; GLUTAMIC ACID; IMIDAZO[1,2 A]INDENO[1,2 E]PYRAZIN 4 ONE DERIVATIVE; IMIDAZOPYRAZINE DERIVATIVE; KAINIC ACID RECEPTOR; METABOTROPIC RECEPTOR; N METHYL DEXTRO ASPARTIC ACID; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; RPR 117824; RPR 119990; TALAMPANEL; UNCLASSIFIED DRUG;

ACUTE DISEASE; ANTICONVULSANT ACTIVITY; BINDING AFFINITY; BRAIN INJURY; BRAIN ISCHEMIA; CHRONIC DISEASE; CLINICAL TRIAL; DEGENERATIVE DISEASE; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; EPILEPSY; EVIDENCE BASED MEDICINE; HUMAN; IN VIVO STUDY; NERVE CELL NECROSIS; NERVE DEGENERATION; NEUROLOGIC DISEASE; NEUROPROTECTION; NONHUMAN; RECEPTOR BINDING; REVIEW; SIGNAL TRANSDUCTION; STRUCTURE ACTIVITY RELATION;

AMYOTROPHIC LATERAL SCLEROSIS; ANIMALS; ANTICONVULSANTS; EXCITATORY AMINO ACID ANTAGONISTS; GERBILLINAE; IMIDAZOLES; NEUROPROTECTIVE AGENTS; PYRAZINES; RATS; RECEPTORS, AMPA; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 3042843644     PISSN: 13895575     EISSN: None     Source Type: Journal    
DOI: 10.2174/1389557043487411     Document Type: Review

References (35)

1. Choi, D. Trends Neurosci., 1988, 11, 465.
2. For recent reviews, see: Nakanishi, S. Science, 1992, 258, 597;
3. Satkowski, M.; Attwell, D. Trends Neurosci., 1994, 17, 359;
4. Danysz, W.; Parsons, C. G.; Bresink, I.; Quack, G. Drug News Perspect. 1995, 8, 261;
5. Bigge, C. F.; Nikam, S. S. Exp. Opin. Ther. Patents, 1997, 7, 1099;
6. Parsons, C. G.; Danysz, W.; Quack, G. Drug News Perspect., 1998, 11, 523.
7. Barry, M. F.; Ziff, E. B. Current Opinion in Neurobiology, 2002, 12, 279.
8. For recent reviews, see: Chimirri, A; Gitto, R; Zappalà, M. Exp. Opin. Ther. Pat. 1999, 9, 557;
9. Zappalà, M.; Grasso, S.; Micale, N.; Polimeni, S.; De Micheli, C. Mini Reviews in Medicinal Chemistry, 2001, 1, 243;
10. Auberson, Y. P. Drugs of the Future, 2001, 26, 463.
11. Sheardown, M. J.; Nielsen, E. O.; Hansen, A. J.; Jacobsen, P.; Honore, T. Science, 1990, 247, 571.
12. Ohmori, J.; Sakamoto, S.; Kubota, H.; Shimizu-Sasamata, M.; Okada M.; Kawasaki, S.; Hidaka, K.; Togami, J.; Furuya, T.; Murase, K. J. Med. Chem., 1994, 37, 467.
13. Habert, A.; Takahashi, M.; Yamaguchi, T.; Hjelstuen, M.; Haraldseth, O. Brain Res., 1998, 811, 63.
14. Turski, L.; Huth, A.; McDonald, F.; Schneider, H. H.; Neuhaus, R.; Dyrks, T.; Bresink, I.; Ottow, E. Proc. Natl. Acad. Sci. USA, 1998, 95, 10960.
15. Ornstein, P. L.; Arnold, M. B.; Augenstein, N. K. J. Med. Chem., 1993, 36, 2046.
16. Anderson, B.; Harn, N. K.; Hansen, M. M.; Harkness, A.R.; Lodge, D.; Leander, J. D. Bioorg. & Med. Chem. Lett., 1999, 9, 1953.
17. Lee, J. M.; Zipfel, G. J.; Choi, D. W. Nature, 1999, Supplement to Vol. 339, no 6738, 47;
18. Parson, C. G.; Danyssz, W.; Quack, G. Drug News Perspect, 1998, 11, 523.
19. Mignani, S.; Aloup, J. -C.; Blanchard, J. -C.; Bohme, G. A.; Boireau, A.; Damour, D.; Debono, M. W.; Dubroeucq, M. -C.; Genevois-Borella, A.; Imperato, A.; Jimonet, P.; Pratt, J.; Randle, J. C. R.; Reibaud, M.; Ribeill, Y.; Stutzmann, J. -M. Drug. Dev. Res., 1999, 48, 121.
20. All the compounds described therein exhibited MS, NMR and IR spectra in agreement with the claimed structures. Noe effects as well as HMBC correlations also confirmed the skeletal arrangements when necessary. All the compounds submitted to biological assays - either in vitro or in vitro gave satisfied elemental analysis (C, H, N) results.
21. Jimonet, P.; Boireau, A.; Chevé, M.; Damour, D.; Genevois-Borella, A.; Imperato, A.; Pratt, J.; Randle, J. C. R.; Ribeill, Y.; Stutzmann, J. -M.; Mignani, S. Bioorg. & Med. Chem. Lett., 1999, 9, 2921.
22. Mignani, S.; Bohme, G. A.; Boireau, A.; Chevé, M.; Damour, D.; Debono, M-W.; Genevois-Borella, G.; Imperato, A.; Jimonet, P.; Pratt, J.; Randle, J. C. R.; Ribeill, Y.; Vuilhorgne, M.; Stutzmannn, J. -M. Bioorg. & Med. Chem. Lett., 2000, 10, 591.
23. Stutzmann, J-M.; Bohme, G. A.; Boireau, A.; Damour, D.; Debono, M. -W.; Genevois-Borella, A.; Jimonet, P.; Pratt, J.; Randle, J. C. R.; Ribeill, Y.; Vuilhorgne, M.; Mignani, S. Bioorg. & Med. Chem. Lett., 2001, 11, 1205.
24. Jimonet, P.; Chevé, M.; Bohme, G. A.; Boireau, A.; Damour, D.; Debono, M-W.; Genevois-Borella, G.; Imperato, A.; Pratt, J.; Randle, J. C. R.; Ribeill, Y.; Vuilhorgne, M.; Stutzmannn J. -M.; Mignani, S. Bioorg. & Med. Chem. 2000, 8, 2217.
25. Stutzmann, J. -M.; Bohme, G. A.; Boireau, A.; Damour, D.; Debono, M.-W.; Genevois-Borella, A.; Imperato, A.; Jimonet, P.; Pratt, J.; Randle, J. C. R.; Ribeill, Y.; Vuilhorgne, M.; Mignani, S. Bioorg. & Med. Chem. Lett., 2000, 10, 1133.
26. Pratt, J.; Jimonet, P.; Bohme, G. A.; Boireau, A.; Damour, D.; Debono, M. -W.; Genevois-Borella, A.; Randle, J. C. R.; Ribeill, Y.; Stutzmann, J. -M.;Vuilhorgne, M.; Mignani, S. Bioorg. & Med. Chem. Lett., 2000, 10, 2749.
27. Mignani, S.; Bohme, G. A.; Birraux, G.; Boireau, A.; Jimonet, P.; Damour, D.; Genevois-Borella, A.; Debono, M. -W.; Pratt, J.; Vuilhorgne, M.; Wahl, F.; Stutzmann, J. -M. Bioorg. & Med. Chem. Lett., 2000, 10, 2749.
28. Jimonet, P.; Bohme, G. A.; Bouquerel, J.; Boireau, A.; Damour, D.; Debono, M-W.; Genevois-Borella, A.; Hardy, J. -C.; Hubert, P.; Manfré, F.; Nemecek, P.; Pratt, J.; Randle, J. C. R.; Ribeill, Y.; Stutzmann, J-M.; Vuilhorgne, M.; Mignani, S. Bioorg. & Med. Chem. Lett., 2001, 11, 127.
29. Honoré, T., Drejer, J. J. Neurochem., 1988, 51, 457.
30. Mignani, S.; Bohme, G. A.; Birraux, G.; Boireau, A.; Jimonet, P.; Damour, D.; Genevois-Borella, A.; Debono, M. -W.; Pratt, J.; Vuilhorgne, M.; Wahl, F.; Stutzmann, J. -M. Bioorg. & Med. Chem., 2002, 10, 1627.
31. Canton, T.; Bohme, G. A.; Boireau, A.; Bordier, F.; Mignani, S.; Jimonet, P.; Ghafoor, J.; Alavijeh, M.; Stygall, J.; Roberts, S.; Brealey, C.; Vuilhorgne, M.; Debono, M. -W.; Le Guern, S.; Laville, M.; Briet, D.; Roux, M.; Stutzmann, J-M.; Pratt, J. J. Pharmacol. Exp. Ther., 2001, 299, 314.
32. Debono, M-W.; Le guern, J.; Canton, T.; Doble, A.; Pradier, L. Eur. J. Pharmacol. 1993, 235, 283.
33. Swinyard, E. A.; Brown, W. C.; Goodmann, L. S. J. Pharmacol. Exp. Ther., 1952, 106, 319.
34. Chapman, A. G.; Smith, J. M.; meldrum, B. S. Arzneimittelforschung, 1984, 34, 1261.
35. Litchfield, J. T.; Wilcoxon, F. J. Pharmacol. Exp. Ther., 1949, 243, 603.