Rational design, synthesis, and structure-activity relationship of benzoxazolones: New potent mglu5 receptor antagonists based on the fenobam structure

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 5, 2007, Pages 1302-1306

  Ceccarelli, Simona M ^a   Jaeschke, Georg ^a   Buettelmann, Bernd ^a   Huwyler, Jörg ^b   Kolczewski, Sabine ^a   Peters, Jens Uwe ^a   Prinssen, Eric ^a   Porter, Richard ^a   Spooren, Will ^a   Vieira, Eric ^a  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

^b UNIVERSITY OF APPLIED SCIENCES AND ARTS NORTHWESTERN SWITZERLAND   (Switzerland)

Author keywords

Anxiety; Benzoxazolone; Fenobam; mGluR5; MPEP

Indexed keywords

BENZOXAZOLE DERIVATIVE; FENOBAM; METABOTROPIC RECEPTOR 5; METABOTROPIC RECEPTOR ANTAGONIST; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANXIETY; ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; HIGH THROUGHPUT SCREENING; IN VIVO STUDY; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTI-ANXIETY AGENTS; ANXIETY; BENZOXAZOLES; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; IMIDAZOLES; MODELS, ANIMAL; PHARMACOKINETICS; PROTEIN BINDING; RATS; RECEPTORS, METABOTROPIC GLUTAMATE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33846901189     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.12.006     Document Type: Article

References (43)

1. Dingledine R., Borges K., Bowie D., and Traynelis S.F. Pharmacol. Rev. 51 (1999) 7
2. Pin J., De Colle C., Bessis A., and Acher F.Eur. J. Pharmacol. 375 (1999) 277
3. O'Hara L.J., Sheppard P.O., Thogersen H., Venezia D., Haldema B.A., MacGrane V., Houamed K.M., Thomsen C., Gilbert E.R., and Mulvihill E.R. Neuron 11 (1993) 41
4. Kew J.N.C., and Kemp J.A. Psychopharmacology 179 (2005) 4
5. Knöpfel T., Kuhn R., and Allgeier H. J. Med. Chem. 38 (1995) 1417
6. Varney M.A., and M Gereau R.W.I. Curr. Drug Targets: CNS Neurol. Disord. 1 (2002) 283
7. Spooren W.P.J.M., Gasparini F., Salt T.E., and Kuhn R. Trends Pharmacol. Sci. 22 (2001) 331
8. Shigemoto R., Nomura S., Ohishi H., Sugihara H., Nakanishi S., and Mizuno N. Neurosci. Lett. 163 (1993) 53
9. Romano C., Sesma M.A., McDonald C.T., O'Malley K., VandenPol A.N., and Olney J.W. J. Comp. Neurol. 355 (1995) 455
10. Ballard T.M., Woolley M.L., Prinssen E., Huwyler J., Porter R., and Spooren W. Psychopharmacology 179 (2005) 218
11. Spooren W., and Gasparini F. Drug News Perspectives 17 (2004) 251
12. Swanson C.J., Bures M., Johnson M.P., Linden A.-M., Monn J.A., and Schoepp D.D. Nat. Rev. Drug Disc. 42 (2005) 131
13. Mutel V. Expert Opin. Ther. Patents 12 (2002) 1845 and references therein
14. Pietraszek M., Sukhanov I., Maciejak P., Szyndler J., Gravius A., Wislowska A., Plaznik A., Bespalov A.Y., and Danysz W. Eur. J. Pharmacol. 514 (2005) 25
15. Selected recent patents: Buettelmann, B.; Ceccarelli, S. M.; Jaeschke, G.; Kolczewski, S.; Porter, R. H. P.; Vieira, E. WO2006074884, 2006.
16. Gagliardi, S.; Palombi, G.; Rocher, J.-P. WO 2006048771, 2006.
17. Kuehnert, S.; Oberboersch, S.; Haurand, M.; Jostock, R.; Schiene, K. WO2006002981, 2006.
18. Bessis, A.-S.; Bolea, C.; Bonnet, B.; Epping-Jordan, M.; Poirier, N.; Poli, S.-M.; Rocher, J.-P.; Thollon, Y. WO 2005123703, 2005.
19. Buettelmann, B.; Ceccarelli, S. M.; Jaeschke, G.; Kolczewski, S.; Porter, R. H. P.; Vieira, E. WO2005118568, 2005.
20. Edwards, L.; Isaac, M.; Johansson, M.; Kers, A.; Malmberg, J.; McLeod, D.; Mindis, A.; Staaf, K.; Slassi, A.; Stefanac, T.; Stormann, T.; Wensbo, D.; Xin, T.; Arora, J. US 2005272779, 2005.
21. Agejas-C., Francisco J.; Dressman, B. A.; Gutierrez Sanfeliciano, S.; Henry, S. S.; Martinez Perez, J. A.; Massey, S. M.; Monn, J. A.; Zia-Ebrahimi, M. S. WO2005094822, 2005.
22. Wensbo, D.; Edwards, L.; Isaac, M.; McLeod, D. A.; Slassi, A.; Xin, T.; Stormann, T. M. WO2005066155, 2005.
23. Gasparini, F.; Auberson, Y.; Ofner, S.; WO2003047581, 2003.
24. Selected recent papers:. Kulkarni S.S., Nightingale B., Dersch C.M., Rothman R.B., and Newman A.H. Bioorg. Med. Chem. Lett. 16 (2006) 3371
25. Hammerland L.G., Johansson M., Malmstroem J., Mattsson J.P., Minidis A.B.E., Nilsson K., Peterson A., Wensbo D., Wallberg A., and Oesterlund K. Bioorg. Med. Chem. Lett. 16 (2006) 2467
26. Iso Y., and Kozikowski A.P. Synthesis (2006) 243
27. Tehrani L.R., Smith N.D., Huang D., Poon S.F., Roppe J.R., Seiders T.J., Chapman D.F., Chung J., Cramer M., and Cosford N.D.P. Bioorg. Med. Chem. Lett. 15 (2005) 5061
28. Chua P.C., Nagasawa J.Y., Bleicher L.S., Munoz B., Schweiger E.J., Tehrani L., Anderson J.J., Cramer M., Chung J., Green M.D., King C.D., Reyes-Manalo G., and Cosford N.D.P. Bioorg. Med. Chem. Lett. 15 (2005) 4589
29. Wang B., Vernier J.-M., Rao S., Chung J., Anderson J.J., Brodkin J.D., Jiang X., Gardner M.F., Yang X., and Munoz B. Bioorg. Med. Chem. Lett. 12 (2005) 17
30. Büttelmann B., Peter J.-U., Ceccarelli S., Kolczweski S., Vieira E., Prinssen E.P., Spooren W., Schuler F., Huwyler J., Porter R.H.P., and Jaeschke G. Bioorg. Med. Chem. Lett. 16 (2006) 1892
31. Gasparini F., Lingenhohl K., Stoehr N., Flor P.J., Heinrich M., Vranesic I., Biollaz M., Allgeier H., Heckendorn R., Urwyler S., Varney M.A., Johnson E.C., Hess S.D., Rao S.P., Sacaan A.I., Santori E.M., Velicelebi G., and Kuhn R. Neuropharmacology 38 (1999) 1493
32. Cosford N.D.P., Tehrani L., Roppe J., Schweiger E., Smith N.D., Anderson J., Bristow L., Brodkin J., Jiang X., McDonald I., Rao S., Washburn M., and Varney M.A. J. Med. Chem. 46 (2003) 204
33. Pecknold J.C., McClure D.J., Appeltauer L., Wrzesinski L., and Allan T. J. Clin. Psychopharm. 2 (1982) 129
34. Goldberg M.E., Salama A.I., Patel J.B., and Malick J.B. Neuropharmacology 22 (1983) 1499
35. Porter R.H.P., Jaeschke G., Spooren W., Ballard T.M., Buettelmann B., Kolczweski S., Peters J.-U., Prinssen E., Wichmann J., Vieira E., Muhlemann A., Gatti S., Mutel V., and Malherbe P. J. Pharmacol. Exp. Ther. 315 (2005) 711
36. 3H]MPEP from recombinant mGlu5 receptor, see. Malherbe P., Kratochwil N., Zenner M.-T., Piussi J., Diener C., Kratzeisen C., Fischer C., and Porter R.H.P. Mol. Pharmacol. 64 (2003) 823
37. 2+] in a cell line expressing mGlu5 using a fluorescence imaging plate reader (FLIPR).
38. Wu W.N., McKown L.A., and O'Neill P.J. J. Pharm. Sci. 84 (1995) 185
39. Wǻllberg A., Nilsson K., Oesterlund K., Peterson A., Elg S., Raboisson P., Bauer U., Hammerland L.G., and Mattsons J.P. Bioorg. Med. Chem. Lett. 16 (2006) 1142
40. Jaeschke, G.; Porter, R.; Büttelmann, B.; Ceccarelli, S.M.; Guba, W.; Kuhn, B.; Kolczewski, S.; Mutel, V.; Peters, J.-U.; Ballard, T.; Prinnsen, E.; Vieira, E.; Wichmann, J.; Spooren, W, previous paper in this issue.
41. Bonnefous et al. also reported a similar hypothesis, see. Bonnefous C., Vernier J.-M., Hutchinson J.H., Chung J., Reyes-Manalo G., Kamenecka T. Bioorg. Med. Chem. Lett. 15 (2005) 4350
42. Measurements were performed according to an in-house developed method to assess solubility from a 10 mM DMSO stock solution. This method is similar to the classical thermodynamic shake-flask solubility with the only difference that DMSO is removed in the beginning by an additional lyophilization step. Therefore, this assay is called lyophilization solubility assay (LYSA).
43. Simulated permeation across physiological membranes was determined according to the method described in. Kansy M., Avdeef A., and Fischer H. Drug Discovery Today: Technol. 1 (2004) 349 and references therein