Development of 2-aryl substituted quinazolin-4(3H)-one, pyrido[4,3-d]pyrimidin-4(3H)-one and pyrido[2,3-d]pyrimidin-4(3H)-one derivatives as microsomal prostaglandin E2 synthase-1 inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 24, Issue 20, 2014, Pages 4838-4844

  Banerjee, Abhisek ^a   Pawar, Mahesh Y ^a   Patil, Sandip ^a   Yadav, Pravin S ^a   Kadam, Pradip A ^a   Kattige, Vidya G ^a   Deshpande, Durga S ^a   Pednekar, Pallavi V ^a   Pisat, Monali K ^a   Gharat, Laxmikant A ^a  

^a Glenmark Pharmaceuticals Limited   (India)

Author keywords

Analgesic; Cyclooxygenase; mPGES 1; Prostaglandin E2; Quinazolinone

Indexed keywords

ENZYME INHIBITOR; ISOMERASE; PROSTAGLANDIN E SYNTHASE; PYRIDO(4,3-D)PYRIMIDIN-4(3H)-ONE; PYRIMIDINONE DERIVATIVE; QUINAZOLINONE DERIVATIVE;

ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; HUMAN; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

CELL LINE, TUMOR; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; HUMANS; INTRAMOLECULAR OXIDOREDUCTASES; MOLECULAR STRUCTURE; PYRIMIDINONES; QUINAZOLINONES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84908701505     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2014.08.056     Document Type: Article

References (43)

1. P.J. Jakobsson, S. Thoren, R. Morgenstern, and B. Samuelsson Proc. Natl. Acad. Sci. U.S.A. 96 1999 7220
2. J.Y. Park, M.H. Pillinger, and S.B. Abramson Clin. Immunol. 119 2006 229
3. M. Korotkova, and P.-J. Jakobsson Basic Clin. Pharmacol. Toxicol. 114 2014 64
4. M. Korotkova, and P.-J. Jakobsson Front. Pharmacol. 1 2011 1
5. H.H. Chang, and E.J. Meuillet Future Med. Chem. 2011 1909 3
6. A. Kawabata Biol. Pharm. Bull. 34 2011 1170
7. R.W. Friesen, and J.A. Mancini J. Med. Chem. 51 2008 4059
8. B. Samuelsson, R. Morgenstern, and P.J. Jakobsson Pharmacol. Rev. 59 2007 207
9. S.M. Jachak Curr. Opin. Invest. Drugs 8 2007 411
10. M. Wang, W.L. Song, Y. Cheng, and G.A. Fitzgerald J. Intern. Med. 263 2008 500
11. L.J. Marnett Annu. Rev. Pharmacol. Toxicol. 49 2009 265
12. T. Grosser, S. Fries, and G.A. FitzGerald J. Clin. Invest. 116 2006 4
13. D. Engblom, S. Saha, L. Engström, M. Westman, L.P. Audoly, P.-J. Jakobsson, and A. Blomqvist Nat. Neurosci. 6 2003 1137
14. C.E. Trebino, J.L. Stock, C.P. Gibbons, B.M. Naiman, T.S. Wachtmann, J.P. Umland, K. Pandher, J.-M. Lapointe, S. Saha, M.L. Roach, D. Carter, N.A. Thomas, B.A. Durtschi, J.D. McNeish, J.E. Hambor, P.-J. Jakobsson, T.J. Carty, J.R. Perez, and L.P. Audoly Proc. Natl. Acad. Sci. U.S.A. 100 2003 9044
15. Y. Cheng, M. Wang, Y. Yu, J. Lawson, C.D. Funk, and G.A. FitzGerald J. Clin. Invest. 116 2006 1391
16. B. Cote, L. Boulet, C. Brideau, D. Claveau, D. Ethier, R. Frenette, M. Gagnon, A. Giroux, J. Guay, S. Guiral, J. Mancini, E. Martins, F. Massé, N. Méthot, D. Riendeau, J. Rubin, D. Xu, H. Yu, Y. Ducharme, and R.W. Friesen Bioorg. Med. Chem. Lett. 17 2007 6816
17. D. Xu, S.E. Rowland, P. Clark, A. Giroux, B. Cote, S. Guiral, M. Salem, Y. Ducharme, R.W. Friesen, N. Méthot, J. Mancini, L. Audoly, and D. Riendeau J. Pharmacol. Exp. Ther. 326 2008 754
18. S.-C. Pawelzik, N.R. Uda, L. Spahiu, C. Jegerschöld, P. Stenberg, H. Hebert, R. Morgenstern, and P.-J. Jakobsson J. Biol. Chem. 285 2010 29254
19. G. Corso, I. Coletta, and R. Ombrato J. Chem. Inf. Model. 53 2013 1804
20. J. Wang, D. Limburg, J. Carter, G. Mbalaviele, J. Gierse, and M. Vazquez Bioorg. Med. Chem. Lett. 20 2010 1604
21. G. Mbalaviele, A.M. Pauley, A.F. Shaffer, B.S. Zweifel, S. Mathialagan, S.J. Mnich, O.V. Nemirovskiy, J. Carter, J.K. Gierse, J.L. Wang, M.L. Vazquez, W.M. Moore, and J.L. Masferrer Biochem. Pharmacol. 79 2010 1445
22. G.B. Arhancet, D.P. Walker, S. Metz, Y.M. Fobian, S.E. Heasley, D.E. Jones, M.J. Hayes, J.S. Carter, J.R. Springer, H.-F. Lu, A.F. Shaffer, G.M. Jerome, M.T. Baratta, B.S. Zweifel, W.M. Moore, J.L. Masferrer, and M.L. Vazquez Bioorg. Med. Chem. Lett. 23 2013 1114
23. F. Salazar, M.L. Vazquez, J.L. Masferrer, G. Mbalaviele, M.T. Llinas, F. Saez, G. Arhancet, and F.J. Salazar Am. J. Physiol. Renal Physiol. 306 2014 F6
24. 'A Study of LY3023703 Testing Pain Relief after Wisdom Teeth Removal'. Clinical trial identifier: NCT01872910 at www.clinicaltrial.gov.
25. L. Chen, G. Yang, J. Monslow, L. Todd, D.P. Cormode, J. Tang, G.R. Grant, J.H. DeLong, S.Y. Tang, J.A. Lawson, E. Pure, and G.A. FitzGerald Proc. Natl. Acad. Sci. U.S.A. 111 2014 6828
26. 'Lipidomics Screening of Anti-inflammatory Drugs and Drug Candidates'. Clinical trial identifier: NCT02095288 at www.clinicaltrial.gov.
27. Bylund, J.; Ek, M.; Holenz, J.; Johansson, M. H.; Kers, A.; Narhi, K.; Nordvall, G.; Ohberg. L.; Sohn, D.; Viklund, J.; von Berg, S. Bis-(sulfonylamino) derivatives in therapy. PCT Intl. Appl. WO/2009/064250, 2009.
28. J. Bylund, A. Annas, D. Hellgren, S. Bjurström, H. Andersson, and A. Svanhagen Drug Metab. Dispos. 41 2013 634
29. J.-F. Chiasson, L. Boulet, C. Brideau, A. Chau, D. Claveau, B. Côté, D. Ethier, A. Giroux, J. Guay, S. Guiral, J. Mancini, F. Massé, N. Méthot, D. Riendeau, P. Roy, J. Rubin, D. Xu, H. Yu, Y. Ducharme, and R.W. Friesen Bioorg. Med. Chem. Lett. 21 2011 1488
30. T.Y.H. Wu, H. Juteau, Y. Ducharme, R.W. Friesen, S. Guiral, L. Dufresne, H. Poirier, M. Salem, D. Riendeau, J. Mancini, and C. Brideau Bioorg. Med. Chem. Lett. 20 2010 6978
31. T. Shiro, K. Kakiguchi, H. Takahashi, H. Nagata, and M. Tobe Bioorg. Med. Chem. 21 2013 2868
32. Pfau, R.; Arndt, K.; Doods, H.; Klinder, K.; Kuelzer, R.; Lubriks, D.; Mack, J.; Pelcman, B.; Priepke, H.; Roenn, R.; Stenkamp, D.; Suna, E. 3H-Imidazo4,5-cpyridine-6-carboxamides as anti-inflammatory agents. PCT Intl. Appl. WO/2010/100249, 2010.
33. Hughes, N. E.; Woods, T. A.; Norma, B. H. Novel imidazole derivatives useful for the treatment of arthiritis. PCT Intl. Appl. WO/2012/161965, 2012.
34. Wannberb, J.; Alterman, M.; Stenberg, P.; Westman, J. Preparation of 1,3-disubstituted benzene derivatives as microsomal prostaglandin E synthase inhibitors. PCT Intl. Appl. WO/2009/103778, 2009.
35. Priepke, H.; Doods, H.; Kuelzer, R.; Pfau, R.; Stenkamp, D.; Roenn, R.; Pelcman, B. Inhibitor of microsomal prostaglandin E2 synthase-1. PCT Intl. Appl. WO/2011/048004, 2011.
36. Otsu, H. Preparation of benzene-fused 5-membered heterocyclic compounds as inhibitors of microsomal prostaglandin E synthase-1 (mPGES-1). PCT Intl. Appl. WO/2013/024898, 2013.
37. Gharat, L. A.; Banerjee, A.; Pawar, M. Y.; Khairatkar-Joshi, N.; Kattige, V. G. Substituted bicyclic heteroaryl compounds as mPGES-1 inhibitors. PCT Intl. Appl. WO/2013/038308, 2013.
38. Gharat, L. A.; Banerjee, A.; Khairatkar-Joshi, N.; Kattige, V. G. Phtahlazinone derivatives as mPGES-1 inhibitors. PCT Intl. Appl. WO/2013/072825, 2013.
39. Gharat, L. A.; Banerjee, A.; Khairatkar-Joshi, N.; Kattige, V. G. Bicyclic compounds as mPGES-1 inhibitors. PCT Intl. Appl. WO/2013/118071, 2013.
40. M. Depré, E. Ehrich, A. Van Hecken, I. De Lepeleire, A. Dallob, P. Wong, A. Porras, B.J. Gertz, and P.J. De Schepper Eur. J. Clin. Pharmacol. 56 2000 167
41. D.R. Huntjens, M. Danhof, and O.E. Della Pasqua Rheumatology 44 2005 846
42. D.R. Huntjens, D.J. Spalding, M. Danhof, and O.E. Della Pasqua Br. J. Pharmacol. 148 2006 396
43. B.A. Bhat, and D.P. Sahu Synth. Commun. 34 2004 2169