Pentacycle derivatives as cannabinoid CB1 receptor ligands

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 23, 2009, Pages 6632-6636

  Lee, Suk Ho ^a   Seo, Hee Jeong ^a   Kim, Min Ju ^a   Kang, Suk Youn ^a   Lee, Sung Han ^a   Ahn, Kwangwoo ^a   Lee, MinWoo ^a   Han, Ho Kyun ^a   Kim, Jeongmin ^a   Lee, Jinhwa ^a  

^a Green Cross Company   (South Korea)

Author keywords

Antagonist; Antiobesity; Cannabinoid; Pentacycle; Rimonabant

Indexed keywords

2 [5 (4 BROMOPHENYL) 1 (2,4 DICHLOROPHENYL) 4 (5 METHYL 1,3,4 THIADIAZOL 2 YL) 1H PYRAZOL 3 YL] 5 [1 (TRIFLUOROMETHYL)CYCLOPROPYL] 1,3,4 OXADIAZOLE; ANTIOBESITY AGENT; CANNABINOID 1 RECEPTOR; CANNABINOID 1 RECEPTOR ANTAGONIST; CARBOXYLIC ACID; LIGAND; PENTACYCLE DERIVATIVE; REAGENT; RIMONABANT; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; BROMINATION; CHEMICAL MODIFICATION; CHO CELL; CYCLIZATION; DRUG ABSORPTION; DRUG CLEARANCE; DRUG ELIMINATION; DRUG HALF LIFE; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG SYNTHESIS; FEMALE; IC 50; IN VITRO STUDY; MICROWAVE IRRADIATION; NONHUMAN; OXIDATION; RAT;

ANIMALS; DRUG DESIGN; HUMANS; LIGANDS; MOLECULAR STRUCTURE; PYRAZOLES; RATS; RECEPTOR, CANNABINOID, CB1; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 71749089474     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.10.015     Document Type: Article

References (39)

1. Lee J., Song K.-S., Kang J., Lee S.H., and Lee J. Curr. Top. Med. Chem. 9 (2009) 564
2. Lange J.H.M., and Kruse C.G. Drug Discovery Today 10 (2005) 693
3. Howlett A.C., Breivogel C.S., Childers S.R., Deadwyler S.A., Hampson R.E., and Porrio L.J. Neuropharmacology 47 (2004) 345
4. Lafontan M., Piazza P.V., and Girard J. Diabetes Metab. 33 (2007) 85 and reference cited therein
5. Carrier E.J., Kearn C.S., Barkmeier A.J., Breese N.M., Yang W., Nithipatikom K., Pfister S.L., Cambell W.B., and Hillard C.J. Mol. Pharmacol. 65 (2004) 999
6. Klein T.W., Newton C., Larsen K., Lu L., Perkins I., Nong L., and Friedman H. J. Leukocyte Biol. 74 (2003) 486
7. Rinaldi-Carmona M., Barth F., Héaulme M., Alonso R., Shire D., Congy C., Soubrié P., Breliére J.-C., and le Fur G. Life Sci. 56 (1995) 1941
8. Rinaldi-Carmona M., Barth F., Héaulme M., Shire D., Calandra B., Congy C., Martinez S., Maruani J., Néliat G., Caput D., Ferrara P., Soubrié P., Breliére J.-C., and le Fur G. FEBS Lett. 350 (1994) 240
9. Lange J.H., Coolen H.K., van Stuivenberg H.H., Dijksman J.A., Herremans A.H., Ronken E., Keizer H.G., Tipker K., McCreary A.C., Veerman W., Wals H.C., Stork B., Verveer P.C., den Hartog A.P., de Jong N.M., Adolfs T.J., Hoogendoorn J., and Kruse C.G. J. Med. Chem. 47 (2004) 627
10. Griffith D.A., Hadcock J.R., Black S.C., Iredale P.A., Carpino P.A., DaSilva-Jardine P., Day R., DiBrino J., Dow R.L., Landis M.S., O'Connor R.E., and Scott D.O. J. Med. Chem. 52 (2009) 234
11. Lin L.S., Lanza T.J., Jewell J.J.P., Liu P., Shah S.K., Qi H., Tong X., Wnag J., Xu S.S., Fong T.M., Shen C.-P., Lao J., Xiao J.C., Shearman L.P., Stribling D.S., Rosko K., Strack A., Marsh D.J., Feng Y., Kumar S., Samuel K., Yin W., der Ploeg L.V., Mills S.G., MacCoss M., Goulet M.T., and Hagmann W.K. J. Med. Chem. 49 (2006) 7584
12. Barth, F.; Congy, C.; Martinez, S.; Rinaldi, M. WO97/19063, 2000.
13. Barth, F.; Casellas, P.; Congy, C.; Martinez, S.; Rinaldi, M. C07D/23114, 1995.
14. Hutst D.P., Lynch D.L., Barnett-Norris J., Hyatt S.M., Seltzman H.H., Zhong M., Song Z.-H., Nie J., Lewis D., and Reggio P.H. Mol. Pharmacol. 62 (2002) 1274
15. Shim J.-Y., Welsh W.J., Cartier E., Edwards J.L., and Howlett A.C. J. Med. Chem. 45 (2002) 1447
16. Dow, L. R. U.S. Patent 2004/0077650 A1, 2004.
17. Coe, J. W. U.S. Patent 2005/0043327 A1, 2005.
18. Barth, F.; Congy, C.; Gueule, P.; Rinaldi-Carmona, M.; Van Broeck, D. PCT Patent Application WO2006/087480A1, 2006.
19. Kang S.Y., Lee S.-H., Seo H.J., Jung M.E., Ahn K., Kim J., and Lee J. Bioorg. Med. Chem. Lett. 18 (2008) 2385
20. Barth, F.; Congy, C.; Gueule, P.; Ridaldi-Carmona, M.; Van Brodeck, D. PCT Patent WO 2006/087480 A1, 2006.
21. Moritani, Y. PCT Patent WO 2007/046550 A1, 2007.
22. Lee S.H., Seo H.J., Lee S.-H., Jung M.E., Park J.-H., Yoo J., Yun H., Na J., Kang S.Y., Song K.-S., Kim M.-a., Chang C.-H., Kim J., and Lee J. J. Med. Chem. 51 (2008) 7216
23. Lee S.H., Seo H.J., Kim M.J., Kang S.Y., Song K.S., Lee S.-H., Jung M.E., Kim J., and Lee J. Bioorg. Med. Chem. Lett. 19 (2009) 1899
24. Seo H.J., Kim M.J., Song K.-S., Lee S.-H., Jung M.E., Kim M.-S., Park H.-J., Yoo J., Chang C.-H., Kim J., and Lee J. Future Med. Chem. 1 (2009) 947
25. Kim M.J., Kim J.Y., Seo H.J., Lee J., Lee S.-H., Kim M.-S., Kang J., Kim J., and Lee J. Bioorg. Med. Chem. Lett. 19 (2009) 4692
26. Hilderbrandt A.L., Kelly-Sullivan D.M., and Black S.C. Eur. J. Pharmacol. 462 (2003) 125
27. Lan R., Liu Q., Fan P., Lin S., Fernando S.R., McCallion D., Pertwee R., and Makriyannis A. J. Med. Chem. 42 (1999) 769
28. Amengual, R.; Marsol, C.; Mayeux, E.; Sierra, M.; Wagner, P. PCT Patent WO 2006/133926 A1, 2006.
29. Brain C.T., Paul J.M., Loong Y., and Oakely P.J. Tetrahedron Lett. 40 (1999) 3275
30. Brain C.T., and Brunton S.A. Synlett (2001) 382
31. Kiryanov A.A., Sampson P., and Seed A.J. J. Org. Chem. 66 (2001) 7925
32. Dess D.B., and Martin J.C. J. Org. Chem. 48 (1983) 4155
33. Kuster J.E., Stevenson J.I., Ward S.J., D'Ambra T.E., and Haycock D.A. J. Pharmacol. Exp. Ther. 264 (1993) 1352
34. Murphy J.W., and Kendall D.A. Biochem. Pharmacol. 65 (2003) 1623
35. 50 was determined from three independent experiments.
36. As of November 5, 2008, Sanofi-Aventis, Merck, and Pfizer announced that they have decided to discontinue their ongoing clinical development programs about rimonabant (SR141716), taranabant (MK-0364), and otenabant (CP-945,598), respectively, based on changing regulatory perspectives on the risk/benefit profile of the CB1 class and likely new regulatory requirements for approval.
37. Hurst D.P., Lynch D.L., Barnett-Norris J., Hyatt S.M., Seltzman H.H., Zhong M., Song Z.-H., Nie J., Lewis D., and Reggio P.H. Mol. Pharmacol. 62 (2002) 1274
38. Bouaboula M., Perrachon S., Milligan L., Canat X., Rinaldi-Carmona M., Portier M., Barth F., Calandra B., Pecceu F., Lupker J., Maffrand J.P., Le Fur G., and Casellas P. J. Biol. Chem. 272 (1997) 22330
39. Calandra B., Portier M., Kernéis A., Delpech M., Carillon C., Le Fur G., Ferrara P., and Shire D. Eur. J. Pharmacol. 374 (1999) 445