Structure-activity relationship studies of novel pyrazole and imidazole carboxamides as cannabinoid-1 (CB1) antagonists

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 16, 2011, Pages 4913-4918

  Sasmal, Pradip K ^a   Talwar, Rashmi ^a   Swetha, J ^a   Balasubrahmanyam, D ^a   Venkatesham, B ^a   Rawoof, Khaji Abdul ^a   Neelima Devi, B ^a   Jadhav, Vikram P ^a   Khan, Sanjoy K ^a   Mohan, Priya ^a   Srinivasa Reddy, D ^a   Nyavanandi, Vijay Kumar ^a   Nanduri, Srinivas ^a   Shiva K , Kyasa ^a   Kannan, M ^a   Srinivas, P ^a   Nadipalli, Prabhakar ^a   Chaudhury, Hira ^a   Sebastian, V J ^a  

^a DR REDDY'S LABORATORIES LTD   (India)

Author keywords

Cannabinoid 1 (CB1) receptor; CB1 antagonists; DIO mice model; Obesity; Pyrazole and imidazole carboxamides

Indexed keywords

CANNABINOID 1 RECEPTOR ANTAGONIST; IMIDAZOLECARBOXAMIDE; PYRAZOLE; RIMONABANT;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG BINDING; DRUG CONFORMATION; DRUG POTENCY; DRUG SYNTHESIS; DRUG TOLERABILITY; IN VIVO STUDY; MOUSE; NONHUMAN; OBESITY; STRUCTURE ACTIVITY RELATION; WEIGHT REDUCTION;

MUS;

EID: 79960926259     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.06.017     Document Type: Article

References (44)

1. E.E. Kershaw, and J.S. Flier J. Clin. Endocrinol. Metab. 89 2004 2548
2. T.C. Kirkham Behav. Pharmacol. 16 2005 297
3. U. Pagotto, G. Marsicano, D. Cota, B. Lutz, and R. Pasquali Endocrinol. Rev. 27 2006 73
4. I. Matias, M.P. Gonthier, P. Orlando, V. Martiadis, L. De Petrocellis, C. Cervino, S. Petrosino, L. Hoareau, F. Festy, R. Pasquali, R. Roche, M. Maj, U. Pagotto, P. Monteleone, and V. Di Marzo J. Clin. Endocrinol. Metab. 91 2006 3171
5. S. Hao, Y. Avraham, R. Mechoulam, and E.M. Berry Eur. J. Pharmacol. 392 2000 147
6. S. Engeli, J. Böhnke, M. Feldpausch, K. Gorzelniak, J. Janke, S. Bátkai, P. Pacher, J. Harvey-White, F.C. Luft, A.M. Sharma, and J. Jordan Diabetes 54 2005 2838
7. T.C. Kirkham, C.M. Williams, F. Fezza, and V. Di Marzo Br. J. Pharmacol. 136 2002 550
8. C. Ravinet Trillou, C. Delgorge, C. Menet, M. Arnone, and P. Soubrie Int. J. Obes. 28 2004 640
9. O. Jbilo, C. Ravinet-Trillou, M. Arnone, I. Buisson, E. Bribes, A. Péleraux, G. Pénarier, P. Soubrié, G. Le Fur, S. Galigue, and P.J. Casellas FASEB 19 2005 1567
10. Z.D. Thornton-Jones, G.A. Kennett, K.R. Benwell, D.F. Revell, A. Misra, D.M. Sellwood, S.P. Vickers, and P.G. Clifton Pharmacol. Biochem. Behav. 84 2006 353
11. S.P. Vickers, L.J. Webster, A. Wyatt, C.T. Dourish, and G.A. Kennett Psychopharmacology (Berl.) 167 2003 103
12. A.L. Hildebrandt, D.M. Kelly-Sullivan, and S.C. Black Eur. J. Pharmacol. 462 2003 125
13. M. Lafontan, P.V. Piazza, and J. Girard Diabetes Metab. 33 2007 85 and reference cited therein
14. J. Adam, and P. Cowley Expert Opin. Ther. Pat. 12 2002 1475
15. R.G. Pertwee Addict. Biol. 5 2000 37
16. W. Hall Drug Alcohol Rev. 17 1998 433
17. B.L. Hungund, B.S. Basavarajappa, C. Vadasz, G. Kunos, F.R. de Fonseca, G. Colombo, S. Serra, L. Parsons, and G.F. Koob Alcohol. Clin. Exp. Res. 26 2002 565
18. R.G. Pertwee Gut 48 2001 859
19. E.J. Carrier, C.S. Kearn, A.J. Barkmeier, N.M. Breese, W. Yang, K. Nithipatikom, S.L. Pfister, W.B. Cambell, and C. Hillard J. Mol. Pharmacol. 65 2004 999
20. T.W. Klein, C. Newton, K. Larsen, L. Lu, I. Perkins, L. Nong, and H. Friedman J. Leukocyte Biol. 74 2003 486
21. M. Rinaldi-Carmona, F. Barth, M. Héaulme, D. Shire, B. Calandra, C. Congy, S. Martinez, J. Maruani, G. Néliat, and D. Caput FEBS Lett. 350 1994 240
22. R. Lan, Q. Liu, P. Fan, S. Lin, S.R. Fernando, D. McCallion, R. Pertwee, and A. Makriyannis J. Med. Chem. 42 1999 769
23. L.S. Lin, T.J. Lanza, J.P. Jewell, P. Liu, S.K. Shah, H. Qi, X. Tong, J. Wang, S. Xu, T.M. Fong, C.-P. Shen, J. Lao, J. Chen, L.P. Shearman, D.S. Stribling, K. Rosko, A. Strack, D.J. Marsh, Y. Feng, S. Kumar, K. Samuel, W. Yin, L. Van der Ploeg, M.T. Goulet, and W.K. Hagman J. Med. Chem. 49 2006 7584
24. C.-y. Chen, L.F. Frey, S. Shultz, D.J. Wallace, K. Marcantonio, J.F. Payack, E. Vazquez, S.A. Springfield, G. Zhou, P. Liu, G.R. Kieczykowski, A.M. Chen, B.D. Phenix, U. Singh, J. Strine, B. Izzo, and S.W. Krska Org. Process Res. Dev. 11 2007 616
25. L.S. Lin, S. Ha, R.G. Ball, N.N. Tsou, L.A. Castonguay, G.A. Doss, T.M. Fong, C.P. Shen, J.C. Xiao, M.T. Goulet, and W.K. Hagmann J. Med. Chem. 51 2008 2108
26. M.-H. Son, H.D. Kim, Y.N. Chae, M.-K. Kim, C.Y. Shin, G.J. Ahn, S.-H. Choi, E.K. Yang, K.-J. Park, H.W. Chae, H.-S. Moon, S.-H. Kim, Y.-G. Shin, and S.-H. Yoon Int. J. Obes. 34 2010 547
27. M.-E. Patti J. Clin. Invest. 120 2010 2646
28. J. Tam, V.K. Vemuri, J. Liu, S. Bátkai, B. Mukhopadhyay, G. Godlewski, D. Osei-Hyiaman, S. Ohnuma, S.V. Ambudkar, J. Pickel, A. Makriyannis, and G. Kunos J. Clin. Invest. 120 2010 2953
29. http://www.7tm.com.
30. https://www.thomson-pharma.com.
31. P.K. Sasmal, D.S. Reddy, R. Talwar, B. Venkatesham, D. Balasubrahmanyam, M. Kannan, P. Srinivas, K. Shiva Kumar, B. Neelima Devi, V.P. Jadhav, S.K. Khan, P. Mohan, H. Chaudhury, D. Bhuniya, J. Iqbal, and R. Chakrabarti Bioorg. Med. Chem. Lett. 21 2011 562
32. Z.P. Demko, and K.B. Sharpless Org. Lett. 4 2002 2525
33. C.H. Wu, M.S. Hung, J.S. Song, T.K. Yeh, M.C. Chou, C.M. Chu, J.J. Jan, M.T. Hsieh, S.L. Tseng, C.P. Chang, W.P. Hsieh, Y. Lin, Y.N. Yeh, W.L. Chung, C.W. Kuo, C.Y. Lin, H.S. Shy, Y.S. Chao, and K.S. Shia J. Med. Chem. 52 2009 4496
34. J.H.M. Lange, H.H. van Stuivenberg, H.K.A.C. Coolen, T.J.P. Adolfs, A.C. McCreary, H.G. Keizer, H.C. Wals, W. Veerman, A.J.M. Borst, W. de Looff, P.C. Verveer, and C.G. Kruse J. Med. Chem. 48 2005 1823
35. B. Asproni, G. Talani, F. Busonero, A. Pau, S. Sanna, R. Cerri, M.P. Mascia, E. Sanna, and G. Biggio J. Med. Chem. 48 2005 2638
36. H.E. Armstrong, A. Galka, L.S. Lin, T.J. Lanza Jr., J.P. Jewell, S.K. Shah, R. Guthikonda, Q. Truong, L.L. Chang, G. Quaker, V.J. Colandrea, X. Tong, J. Wang, S. Xu, T.M. Fong, C.P. Shen, J. Lao, J. Chen, L.P. Shearman, D.S. Stribling, K. Rosko, A. Strack, S. Ha, L. Van der Ploeg, M.T. Goulet, and W.K. Hagmann Bioorg. Med. Chem. Lett. 17 2007 2184
37. S.H. Lee, H.J. Seo, S.H. Lee, M.E. Jung, J.H. Park, H.J. Park, J. Yoo, H. Yun, J. Na, S.Y. Kang, K.S. Song, M.A. Kim, C.H. Chang, J. Kim, and J. Lee J. Med. Chem. 51 2008 7216
38. http://www.ema.europa.eu/docs/en-GB/document-library/EPAR-Scientific- Discussion/human/000666/WC500021284.pdf.
39. D. Turcotte, J.-A. Le Dorze, F. Esfahani, E. Frost, A. Gomori, and M. Namaka Expert Opin. Pharmacother. 11 2010 17
40. D. Parolaro, N. Realini, D. Vigano, C. Guidali, and T. Rubino Exp. Neurol. 224 2010 3
41. A. Ligresti, S. Petrosino, and V. Di Marzo Curr. Opin. Chem. Biol. 13 2009 321
42. F.J. Bermudez-Silva, M.P. Viveros, J.M. McPartland, and F. Rodriguez de Fonseca Pharmacol. Biochem. Behav. 95 2010 375
43. B. Bosier, G.G. Muccioli, E. Hermans, and D.M. Lambert Biochem. Pharmacol. 80 2010 1
44. A.M. Malfitano, E. Ciaglia, G. Gangemi, P. Gazzerro, C. Laezza, and M. Bifulco Expert Opin. Ther. Targets 15 2011 297