Hair growth stimulator property of thienyl substituted pyrazole carboxamide derivatives as a cb1 receptor antagonist with in vivo antiobesity effect

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 9, 2009, Pages 2546-2550

  Srivastava, Brijesh Kumar ^a   Soni, Rina ^a   Patel, Jayendra Z ^a   Joharapurkar, Amit ^a   Sadhwani, Nisha ^a   Kshirsagar, Samadhan ^a   Mishra, Bhupendra ^a   Takale, Vijay ^a   Gupta, Sunil ^a   Pandya, Purvi ^a   Kapadnis, Prashant ^a   Solanki, Manish ^a   Patel, Harilal ^a   Mitra, Prasenjit ^a   Jain, Mukul R ^a   Patel, Pankaj R ^a  

^a ZYDUS RESEARCH CENTRE   (India)

Author keywords

Antiobesity effect; Bioisosteric replacement; CB1 antagonist; Hair growth stimulator; Thienyl pyrazoles

Indexed keywords

ANTIOBESITY AGENT; CANNABINOID 1 RECEPTOR ANTAGONIST; PYRAZOLE DERIVATIVE; RIMONABANT;

ALOPECIA; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG EFFECT; DRUG SYNTHESIS; FEMALE; HAIR GROWTH; MALE; MOUSE; NONHUMAN; OBESITY; RAT;

ANIMALS; BENZOXAZINES; CHEMISTRY, PHARMACEUTICAL; CHO CELLS; CRICETINAE; CRICETULUS; CYCLIC AMP; DRUG DESIGN; HAIR; INHIBITORY CONCENTRATION 50; MODELS, CHEMICAL; MORPHOLINES; NAPHTHALENES; OBESITY; PIPERIDINES; PYRAZOLES; RECEPTOR, CANNABINOID, CB1;

ANIMALIA;

EID: 64549090033     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.03.046     Document Type: Article

References (37)

1. Pi-Sunyer F.X., Aronne L.J., Heshmati H.M., Devin J., and Rosenstock J. J. Am. Med. Assoc. 295 (2006) 761
2. Muccioli G.G., and Lambert D.M. Expert Opin. Ther. Patents 16 (2006) 1405
3. Muccioli G.G., and Lambert D.M. Curr. Med. Chem. 12 (2005) 1361
4. Lange J.H.M., and Kruse C.G. Drug Discovery Today 10 (2005) 693
5. Lin L.S., Lanza Jr. T.J., Jewell J.P., Liu P., Shah S.K., Qi H., Tong X., Wang 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., Van der Ploeg L.H.T., Goulet M.T., and Hagmann W.K. J. Med. Chem. 49 (2006) 7584
6. Lange J.H.M., Coolen H.K.A.C., van Stuivenberg H.H., Dijksman J.A.R., Herremans A.H.J., 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.J., Adolfs T.J.P., Hoogendoorn J., and Kruse C.G. J. Med. Chem. 47 (2004) 627
7. Pertwee R.G. Pharmacol. Ther. 74 (1997) 129
8. Cota D., Marsicano G., Tschöp M., Grübler Y., Flachskamm C., Schubert M., Auer D., Yassouridis A., Thöne-Reineke C., Ortmann S., Tomassoni F., Cervino C., Nisoli E., Linthorst A.C.E., Pasquali R., Lutz B., Stalla G.K., and Pagotto U. J. Clin. Invest. 112 (2003) 423
9. Klein T.W., Newton C., and Friedman H. Immunol. Today 19 (1998) 373
10. Casanova M.L., Blazquez C., Martinez-Palacio J., Villanueva C., Fernandez-Acenero M.J., Huffman J.W., Jorcano J.L., and Guzman M. J. Clin. Invest. 111 (2003) 43
11. Maccarrone M., Di Rienzo M., Battista N., Gasperi V., Guerrieri P., Rossi A., and Finazzi-Agro A. J. Biol. Chem. 278 (2003) 33896
12. Stander S., Schmelz M., Metze D., Luger T.A., and Rukwied R. J. Dermatol. Sci. 38 (2005) 177
13. Wilkinson J.D., and Williamson E.M. J. Dermatol. Sci. 45 (2007) 87
14. Sorbera L.A., Castaner J., and Silvestre J.S. Drugs Future 30 (2005) 128
15. Telek A., Biro T., Bodo E., Toth B.I., Borbiro I., Kunos G., and Paus R. FASEB J. 21 (2007) 3534
16. Lohray, B. B.; Lohray, V. B.; Srivastava, B. K. WO patent 2006/025069, 2006; Chem. Abstr. 2006, 144, 292751.
17. Srivastava B.K., Joharapurkar A., Raval S., Patel J.Z., Soni R., Raval P., Gite A., Goswami A., Sadhwani N., Patel H., Mishra B., Solanki M., Pandey B., Jain M.R., and Patel P.R. J. Med. Chem. 50 (2007) 5951
18. Srivastava B.K., Jain M., Joharapurkar A., Raval S., Patel J.Z., Raval P., Soni R., Sadhwani N., and Patel P.R. Med. Chem. Res. 15 (2007) 75
19. Sadhwani N., Jain S., Metiya S., Pandya P., Kanani D., Shah S., Srivastava B.K., and Mitra P. Med. Chem. Res. 15 (2007) 216
20. Joharapurkar, A.; Srivastava, B. K.; Mitra, P.; Jain, M. R.; Patel, P. R. Poster No. 208, Keystone Symposia on Molecular and Cellular Biology, Obesity: Peripheral and Central Pathways Regulating Energy Homeostasis, Obesity (J2) www.keystonesymposia.org. January 14-19, 2007; Keystone, Colorado, USA.
21. Srivastava B.K., Soni R., Joharapurkar A., Kalapatapu S., Patel J.Z., Goswami A., Shedage S.A., Kar S.S., Salunke R.P., Gugale S.B., Dhawas A., Kadam P., Mishra B., Sadhwani N., Unadkat V.B., Mitra P., Jain M.R., and Patel P.R. Bioorg. Med. Chem. Lett. 18 (2008) 963
22. Srivastava B.K., Soni R., Joharapurkar A., Kalapatapu S., Patel J.Z., Jha S., Shedage S.A., Gandhi N., Sairam K.V.V.M., Pawar V., Sadhwani N., Mitra P., Jain M.R., and Patel P.R. Bioorg. Med. Chem. Lett. 18 (2008) 3882
23. Lohray, B. B.; Lohray, V. B.; Srivastava, B. K. US patent 0051386, 2008.
24. Srivastava, B. K.; Lohray, B. B.; Lohray, V. B.; Patel, P. R. WO patent 2008/062424, 2008.
25. Lohray, B. B.; Lohray, V. B.; Srivastava, B. K. US patent 0025448, 2006; Chem. Abstr. 2006, 144, 164295.
26. Lazzari, P.; Rulu, S.; Pinna, G. A.; Murineddu, G. US patent 2005/0261281, 2005; Chem. Abstr. 2006, 144, 6785.
27. Tai C.L., Hung M.S., Pawar V.D., Tseng S.L., Song J.S., Hsieh W.P., Chiu H.H., Wu H.C., Hsieh M.T., Kuo C.W., Hsieh C.C., Tsao J.P., Chao Y.S., and Shia K.S. Org. Biomol. Chem. 6 (2008) 447
28. Tseng S.L., Hung M.S., Chang C.P., Song J.S., Tai C.L., Chiu H.H., Hsieh W.P., Lin Y., Chung W.L., Kuo C.W., Wu C.H., Chu C.M., Tung Y.S., Chao Y.S., and Shia K.S. J. Med. Chem. 51 (2008) 5397
29. Farrar M.W., and Levine R. J. Am. Chem. Soc. 72 (1950) 3695
30. Barth, F.; Casellas, P.; Congy, C.; Martinez, S.; Rinaldi, M. US patent 5,462,960, 1995; Chem. Abstr. 1995, 123, 228179.
31. Harrold J.A., Elliott J.C., King P.J., Widdowson P.S., and Williams G. Brain Res. 952 (2002) 232
32. Arnone M., Maruani J., Chaperon F., Thiebot M.H., Poncelet M., Soubrie P., and Le Fur G. Psychopharmacology 132 (1997) 104
33. Vickers S.P., Webster L.J., Wyatt A., Dourish C.T., and Kennett G.A. Psychopharmacology 167 (2003) 103
34. Di Marzo V., Goparaju S.K., Wang L., Liu J., Batkai S., Jaral Z., Fezza F., Miura G.I., Palmiter R.D., Sugiura T., and Kunos G. Nature 410 (2001) 822
35. Martin B.R., Compton D.R., Thomas B.F., Prescott W.R., Little P.J., Razdan R.K., Johnson M.R., Melvin L.S., Mechoulam R., and Ward S.J. Pharmacol. Biochem. Behav. 40 (1991) 471
36. Pertwee R.G. Br. J. Pharmacol. 46 (1972) 753
37. McMahon L.R., and Koek W. Eur. J. Pharmacol. 569 (2007) 70