Synthesis and structure-activity relationship of N-(3-azabicyclo[3.1.0]hex- 6-ylmethyl)-5-(2-pyridinyl)-1,3-thiazol-2-amines derivatives as NPY Y5 antagonists

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 16, 2010, Pages 4741-4744

  Biagetti, Matteo ^a   Leslie, Colin Philip ^a   Mazzali, Angelica ^a   Seri, Catia ^a   Pizzi, Domenica Antonia ^a   Bentley, Jonathan ^a   Genski, Thorsten ^a   Fabio, Romano Di ^a   Zonzini, Laura ^a   Caberlotto, Laura ^a  

^a GSK   (Italy)

Author keywords

Antagonists; Neuropeptide Y; NPY Y5

Indexed keywords

AZABICYCLO DERIVATIVE; HEXANE; NEUROPEPTIDE Y RECEPTOR ANTAGONIST; NEUROPEPTIDE Y5 RECEPTOR; PYRIDINE DERIVATIVE; THIAZOLE DERIVATIVE; AMINE; NEUROPEPTIDE Y RECEPTOR;

ANIMAL EXPERIMENT; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CONTROLLED STUDY; DRUG SYNTHESIS; ISOMER; LIVER BLOOD FLOW; NONHUMAN; PLASMA CLEARANCE; RAT; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; ANIMAL; ANTAGONISTS AND INHIBITORS; CELL LINE; CHEMISTRY; HUMAN; METABOLISM; STEREOISOMERISM; SYNTHESIS;

AMINES; ANIMALS; AZABICYCLO COMPOUNDS; CELL LINE; HUMANS; RATS; RECEPTORS, NEUROPEPTIDE Y; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

RATTUS;

EID: 77955422760     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.06.140     Document Type: Article

References (35)

1. K. Tatemoto, M. Carlquist, and V. Mutt Nature 296 1982 659
2. M. Hammond IDrugs 4 2001 920
3. D. Larhammar, A. Wraith, M.M. Berglund, S.K. Holmberg, and I. Lundell Peptides 22 2001 295
4. T.E. Adrian, J.M. Allen, S.R. Bloom, M.A. Ghatei, M.N. Rossor, G.W. Roberts, T.J. Crow, K. Tatemoto, and J.M. Polak Nature 306 1983 585
5. Y. Dumont, J.-C. Martel, A. Fournier, S. St-Pierre, and R. Quirion Prog. Neurobiol. 38 1992 125
6. B.G. Stanley, and S.F. Leibowitz Life Sci 35 1984 2635
7. J.T. Clark, P.S. Kalra, W.R. Crowley, and S.P. Kalra Endocrinology 115 1984 427
8. H. Herzog, D. Boey, and S. Lin Neuropeptides 38 2004 189
9. T. Hokfelt, C. Broberger, X. Zhang, M. Diez, J. Kopp, Z. Xu, M. Landry, L. Bao, M. Schalling, J. Koistinaho, S.J. DeArmond, S. Prusiner, J. Gong, and J.H. Walsh Brain Res. Brain Res. Rev. 26 1998 154
10. C. Gerald, M.W. Walker, L. Criscione, E.L. Gustafson, C. Batzl-Hartmann, K.E. Smith, P. Vaysse, M.M. Durkin, T.M. Laz, D.L. Linemeyer, A.O. Schaffhauser, S. Whitebread, K.G. Hofbauer, R.I. Taber, T.A. Branchek, and R.L. Weinshank Nature 382 1996 168
11. M.M. Kamiji, and A. Inui Endocr. Rev. 28 2007 664
12. S.R. Ladyman, and B. Woodside Physiol. Behav. 97 2009 91
13. N.R. Levens, J.-P. Galizzi, and M. Félétou CNS Neurol. Disord. Drug Targets 5 2006 263
14. A. Ishihara, A. Katani, S. Mashiko, T. Tanaka, M. Hidaka, A. Gomori, H. Iwaasa, N. Murai, S.-I. Egashira, T. Murai, Y. Mitobe, H. Matsushita, O. Okamoto, N. Sato, M. Jitsuka, T. Fukuroda, T. Ohe, X. Guan, D.J. MacNeil, L.H.T. Van der Ploeg, M. Nishikibe, Y. Ishii, M. Ihara, and T. Fukami PNAS 103 2006 7154
15. D.J. Marsh, G. Hollopeter, K.E. Kafer, and R.D. Palmiter Nat. Med. 4 1998 718
16. P.J. Larsen, and D.P.D. Woldbye Nat. Med. 4 1998 671
17. D.J. MacNeil Curr. Top. Med. Chem. 7 2007 1721
18. N. Sato, Y. Ogino, S. Mashiko, and M. Ando Expert Opin. Ther. Patents 19 2009 1401
19. T. Sakamoto, M. Moriya, H. Tsuge, T. Takahashi, Y. Haga, K. Nohoshita, O. Okamoto, H. Takahashi, A. Sakuraba, T. Hirohashi, T. Shibata, T. Kanno, J. Ito, H. Iwaasa, A. Gomori, A. Ishihara, T. Fukuroda, A. Kanatani, and T. Fukami Bioorg. Med. Chem. 17 2009 5015
20. K.W. Gillman, M.A. Higgins, G.S. Poindexter, M. Browning, W.J. Clarke, S. Flowers, J.E. Grace, J.B. Hoga, R.T. McGovern, L.G. Iben, G.K. Mattson, A. Ortiz, S. Rassnick, J.W. Russel, and I. Antal-Zimanyi Bioorg. Med. Chem. 14 2006 5517
21. M. Nettekoven, W. Guba, W. Neidhart, P. Mattei, P. Pflieger, J.-M. Plancher, and S. Taylor ChemMedChem 1 2006 45
22. A. Torrens, J. Mas, A. Port, J.A. Castrillo, O. Sanfeliu, X. Guitart, A. Dordal, G. Romero, M.A. Fisas, E. Sanchez, E. Hernandez, P. Perez, R. Perez, and H. Bischmann J. Med. Chem. 48 2005 2080
23. H. Rueeger, M. Gerspacher, P. Buehlmayer, P. Rigollier, Y. Yamaguchi, T. Schmidlin, S. Whitebread, B. Nuesslein-Hildesheim, N. Hanspeter, and C. Leoluca Bioorg. Med. Chem. Lett. 14 2004 2451
24. C.J. Aquino, J.M. Ramanjulu, D. Heyer, A. Daniels, F. Palazzo, and M. Bezube Bioorg. Med. Chem. 2004 2691
25. R.L. Elliot, R.M. Oliver, J.A. LaFlamme, M.L. Gillaspy, M. Hammond, R.F. Hank, T.S. Maurer, D.L. Baker, P.A. DaSilva-Jardine, R.W. Stevenson, C.C. Mack, and J.V. Cassella Bioorg. Med. Chem. Lett. 13 2003 3593
26. S. Tabuchi, H. Itani, Y. Sakata, H. Oohashi, and Y. Satoh Bioorg. Med. Chem. Lett. 12 2002 1171
27. C. Fotsch, J.D. Sonnenberg, N. Chen, C. Hale, W. Karbon, and M.H. Norman J. Med. Chem. 44 2001 2344
28. C.P. Kordik, C. Luo, B.C. Zanoni, T.W. Levenberg, S.J. Wilson, A.H. Vaidya, J.J. Crooke, D.I. Rosenthal, and A.B. Reitz Bioorg. Med. Chem. Lett. 11 2001 2287
29. N. Erondu, I. Gantz, B. Musser, S. Suryawanshi, M. Mallick, C. Addy, J. Cote, G. Bray, K. Fujioka, H. Bays, P. Hollander, S.M. Sanabria-Bohorquez, W. Eng, B. Lngström, R.J. Hargreaves, H.D. Burns, A. Kanatani, T. Fukami, D.J. MacNeil, K.M. Gottesdiener, J.M. Amatruda, K.D. Kaufman, and S.B. Heymsfield Cell Metab. 4 2006 275
30. N. Erondu, C. Addy, K. Lu, M. Mallick, B. Musser, I. Gantz, J. Proietto, A. Astrup, S. Toubro, A.M. Rissannen, S. Tonstad, W.G. Haynes, K.M. Gottesdiener, K.D. Kaufman, J.M. Amatruda, and S.B. Heysmfield Obesity 15 2007 2027
31. Sørensen, G.; Woldbye, D.; Brucker, P. WO 2009/112033A1.
32. P. Müller, D. Fernandez, P. Nury, and J.-C. Rossier Helv. Chim. Acta 82 1999 935
33. J.L.G. Ruano, C. Fajardo, M.R. Martin, W. Midura, and M. Mikołajczyk Tetrahedron: Asymmetry 15 2004 2475
34. All work involving animals was carried out in accordance with European directive 86/609/EEC governing animal welfare and protection, which is acknowledged by Italian Legislative Decree No. 116, 27 January 1992, and according to internal review performed by the GlaxoSmithKline Committee on Animal Research & Ethics (CARE) and to the company Policy on the Care and Use of Laboratory Animals.
35. B. Le Bourdonnec, and L.K. Leister Curr. Med. Chem. 16 2009 3093