Synthesis and biological evaluation of fenobam analogs as mGlu5 receptor antagonists

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 5, 2007, Pages 1307-1311

  Jaeschke, Georg ^a   Porter, Richard ^a   Büttelmann, Bernd ^a   Ceccarelli, Simona M ^a   Guba, Wolfgang ^a   Kuhn, Bernd ^a   Kolczewski, Sabine ^a   Huwyler, Jörg ^a   Mutel, Vincent ^a   Peters, Jens Uwe ^a   Ballard, Theresa ^a   Prinssen, Eric ^a   Vieira, Eric ^a   Wichmann, Jürgen ^a   Spooren, Will ^a  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

Anxiety; Fenobam; mGluR5; MPEP; Pharmacophore

Indexed keywords

FENOBAM; LIGAND; METABOTROPIC RECEPTOR 5; METABOTROPIC RECEPTOR ANTAGONIST; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANXIETY; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG EFFICACY; DRUG SYNTHESIS; HYPERTHERMIA; IN VIVO STUDY; NONHUMAN; PHARMACOPHORE; RAT;

ANIMALS; ANTI-ANXIETY AGENTS; DRUG DESIGN; HUMANS; IMIDAZOLES; LIGANDS; PYRIDINES; RECEPTORS, METABOTROPIC GLUTAMATE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33846939029     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.12.033     Document Type: Article

References (22)

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. Conn J.P., and Pin J.P. Annu. Rev. Pharmacol. Toxicol. 37 (1997) 205
5. Knöpfel T., Kuhn R., and Allgeier H. J. Med. Chem. 38 (1995) 1417
6. Pagano A., Ruegg D., Litschig S., Stoehr N., Stierlin C., Heinrich M., Floersheim P., Prezeau L., Carroll F., Pin J.-P., Cambria A., Vranesic I., Flor P.J., Gasparini F., and Kuhn R. J. Biol. Chem. 275 (2000) 33750
7. 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
8. Spooren W.P.J.M., Gasparini F., Salt T.E., and Kuhn R. Trends Pharmacol. Sci. 22 (2001) 331
9. Spooren W., Vassout A., Neijt H.C., Kuhn R., Gasparini F., Roux S., Porsolt R.D., and Gentsch C. J. Pharmacol. Exp. Thera. 295 (2000) 1267
10. Ballard T.M., Woolley M.L., Prinssen E., Huwyler J., Porter R., and Spooren W. Psychopharmacology 179 (2005) 218
11. Porter R.H.P., Jaeschke G., Spooren W., Ballard T., Buettelmann B., Kolczewski S., Peters J.-U., Prinssen E., Wichmann J., Vieira E., Muehlemann A., Gatti S., Mutel V., and Malherbe P. J. Pharmacol. Exp. Ther. 315 (2005) 711
12. Pecknold J.C., McClure D.J., Appeltauer L., Wrzesinski L., and Allan T. J. Clin. Psychopharmacol. 2 (1982) 129
13. Malherbe P., Kratochwil N., Muhlemann A., Zenner M.-T., Fischer C., Stahl M., Gerber P.R., Jaeschke G., and Porter R.H.P. J. Neurochem. 98 (2006) 601
14. See also a recent publication describing the SAR of fenobam analogs 6:. Wallberg A., Nilsson K., Oesterlund K., Peterson A., Elg S., Raboisson P., Bauer U., Hammerland L.G., and Mattsson J.P. Bioorg. Med. Chem. Lett. 16 (2006) 1142
15. Alagille D., Baldwin R.M., Roth B.L., Wroblewski J.T., Grajkowska E., and Tamagnan G.D. Bioorg. Med. Chem. Lett. 15 (2005) 945
16. Examples 6b, 6d, 6e, and 6f were described previously in the following references:. Alagille D., Baldwin R.M., Roth B.L., Wroblewski J.T., Grajkowska E., and Tamagnan G.D. Bioorg. Med. Chem. 13 (2005) 197
17. Allgeier, H.; Auberson, Y.; Biollaz, M.; Cosford, N. D.; Gasparini, F.; Heckendorn, R.; Johnson, E. C.; Kuhn, R.; Varney, M. A.; Velicelebi, G. PCT Int. Appl., 1999, 48pp, WO 9902497.
18. Wu W.N., McKown L.A., and O'Neill P.J. J. Pharm. Sci. 84 (1995) 185
19. For the first description of 4l (=1-(5-Chloro-3-thienyl)-3-(1-methyl-4-oxo-2-imidazolin-2-yl)urea), see: Hunkeler, W.; Kyburz, E.; Eur. Pat. Appl., 1980, 21pp, EP 16371.
20. Bare, T. M. Eur. Pat. Appl., 1980, 28pp, EP79-302921.
21. Vogel J.R., Beer B., and Clody D.E. Psychopharmacologia 21 (1971) 1
22. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, Jr., J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Gaussian, Inc., Pittsburgh PA, 1998.