Design, synthesis, and biological evaluation of 1,5-benzothiazepine-4-one derivatives targeting factor VIIa/tissue factor

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 5, 2009, Pages 1386-1391

  Ayral, Erwan ^a   Gloanec, Philippe ^b   Bergé, Gilbert ^a   de Nanteuil, Guillaume ^b   Mennecier, Philippe ^b   Rupin, Alain ^b   Verbeuren, Tony J ^b   Fulcrand, Pierre ^a   Martinez, Jean ^a   Hernandez, Jean François ^a  

^a UNIVERSITÉ DE MONTPELLIER   (France)

^b INSTITUT DE RECHERCHES SERVIER   (France)

Author keywords

1,5 Benzothiazepin 4 one; Factor VIIa; Inhibitors

Indexed keywords

1,5 BENZOTHIAZEPINE 4 ONE DERIVATIVE; BENZOTHIAZEPINE DERIVATIVE; BLOOD CLOTTING FACTOR 7A; BLOOD CLOTTING FACTOR 7A INHIBITOR; MOLECULAR SCAFFOLD; UNCLASSIFIED DRUG;

ARTICLE; DRUG DESIGN; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; IC 50; MOLECULAR MODEL;

DRUG DELIVERY SYSTEMS; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; FACTOR VIIA; HUMANS; THIAZEPINES; THROMBOPLASTIN;

EID: 60749084937     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.01.039     Document Type: Article

References (45)

1. Mackman N. Nature 451 (2008) 914
2. Golino P., Loffredo F., Riegler L., Renzullo E., and Cocchia R. Curr. Opin. Invest. Drugs 6 (2005) 298
3. Nutescu E.A., Shapiro N.L., and Chevalier A. Cardiol. Clin. 26 (2008) 169
4. Prezelj A., Stefanic P., Peternel L., and Urleb U. Curr. Pharm. Des. 13 (2007) 287
5. Turpie A.G.G. Arterioscler. Thromb. Vasc. Biol. 27 (2007) 1238
6. Eriksson B.I., Smith H., Yasothan U., and Kirkpatrick P. Nat. Rev. Drug Discov. 7 (2008) 557
7. Gulseth M.P., Michaud J., and Nutescu E.A. Am. J. Health Syst. Pharm. 65 (2008) 1520
8. Shirk R.A., and Vlasuk G.P. Arterioscler. Thromb. Vasc. Biol. 27 (2007) 1895
9. Lazarus R.A., Olivero A.G., Eigenbrot C., and Kirchhofer D. Curr. Med. Chem. 11 (2004) 2275
10. A selection. Young W.B., Kolesnikov A., Rai R., Sprengeler P.A., Leahy E.M., Shrader W.D., Sangalang J., Burgess-Henry J., Spencer J., Elrod K., and Cregar L. Bioorg. Med. Chem. Lett. 11 (2001) 2253
11. Hanessian S., Therrien E., Granberg K., and Nilsson I. Bioorg. Med. Chem. Lett. 12 (2002) 2907
12. Parlow J.J., Case B.L., Dice T.A., Fenton R.L., Hayes M.J., Jones D.E., Neumann W.L., Wood R.S., Lachance R.M., Girard T.J., Nicholson N.S., Clare M., Stegeman R.A., Stevens A.M., Stallings W.C., Kurumbail R.G., and South M.S. J. Med. Chem. 46 (2003) 4050
13. Klinger O., Matter H., Schudok M., Donghi M., Czech J., Lorenz M., Nestler H.P., Szillat H., and Schreuder H. Bioorg. Med. Chem. Lett. 14 (2004) 3715
14. Sagi K., Fujita K., Sugiki M., Takahashi M., Takehana S., Tashiro K., Kayahara T., Yamanashi M., Fukuda Y., Oono S., Okajima A., Iwata S., Shoji M., and Sakurai K. Bioorg. Med. Chem. 13 (2005) 1487
15. Zbinden K.G., Banner D.W., Ackermann J., D'Arcy A., Kirchhofer D., Ji Y.-H., Tschopp T.B., Wallbaum S., and Weber L. Bioorg. Med. Chem. Lett. 15 (2005) 817
16. Kohrt J.T., Filipski K.J., Cody W.L., Cai C., Dudley D.A., Van Huis C.A., Willardsen J.A., Narasimhan L.S., Zhang E., Rapundalo S.T., Saiya-Cork K., Leadley R.J., and Edmunds J.J. Bioorg. Med. Chem. Lett. 16 (2006) 1060
17. Young W.B., Mordenti J., Torkelson S., Shrader W.D., Kolesnikov A., Rai R., Liu L., Hu H., Leahy E.M., Green M.J., Sprengeler P.A., Katz B.A., Yu C., Janc J.W., Elrod K.C., Marzec U.M., and Hanson S.R. Bioorg. Med. Chem. Lett. 16 (2006) 2037
18. Rai R., Kolesnikov A., Sprengeler P.A., Torkelson S., Ton T., Katz B.A., Yu C., Hendrix J., Shrader W.D., Stephens R., Cabuslay R., Sanford E., and Young W.B. Bioorg. Med. Chem. Lett. 16 (2006) 2270
19. Miura M., Seki N., Koike T., Ishihara T., Niimi T., Hirayama F., Shigenaga T., Sakai-Moritani Y., Sakamoto T., Kawasaki S., Okada M., Ohta M., and Tsukamoto S.-i. Bioorg. Med. Chem. 14 (2006) 7688
20. Krishnan R., Kotian P.L., Chand P., Bantia S., Rowland S., and Babu Y.S. Acta Crystallogr. D Biol. Crystallogr. 63 (2007) 689
21. Shiraishi T., Kadono S., Haramura M., Kodama H., Ono Y., Iikura H., Esaki T., Koga T., Hattori K., Watanabe Y., Sakamoto A., Yoshihashi K., Kitazawa T., Esaki K., Ohta M., Sato H., and Kozono T. Bioorg. Med. Chem. Lett. 18 (2008) 4533
22. Bariwal J.B., Upadhyay K.D., Manvar A.T., Trivedi J.C., Singh J.S., Jain K.S., and Shah A.K. Eur. J. Med. Chem. 43 (2008) 2279
23. Nagao T., Sato M., Nakajima H., and Kiyomoto A. Chem. Pharm. Bull. 21 (1973) 92
24. Budriesi R., Cosimelli B., Ioan P., Carosati E., Ugenti M.P., and Spisani R. Curr. Med. Chem. 14 (2007) 279
25. Amblard M., Daffix I., Bedos P., Bergé G., Pruneau D., Paquet J.-L., Luccarini J.-M., Bélichard P., Dodey P., and Martinez J. J. Med. Chem. 42 (1999) 4185
26. Nagel, A. A. WO 9401421, 1994.
27. Buhlmayer, P.; Furet, P. WO 9413651, 1994.
28. Huang P., Loew G.H., Funamizu H., Mimura M., Ishiyama N., Hayashida M., Okuno T., Shimada O., Okuyama A., Ikegami S., Nakano J., and Inoguchi K. J. Med. Chem. 44 (2001) 4082
29. Skiles J.W., Sorcek R., Jacober S., Miao C., Mui P.W., McNeil D., and Rosenthal A.S. Bioorg. Med. Chem. Lett. 3 (1993) 773
30. Das J., Robl J.A., Reid J.A., Sun C.-Q., Misra R.N., Brown B.R., Ryono D.E., Asaad M.M., Bird J.E., Trippodo N.C., Petrillo E.W., and Karanewsky D.S. Bioorg. Med. Chem. Lett. 4 (1994) 2193
31. Slade J., Stanton J.L., Ben-David D., and Mazzenga G.C. J. Med. Chem. 28 (1985) 1517
32. Itoh K., Kori M., Inada Y., Nishikawa K., Kawamatsu Y., and Sugihara H. Chem. Pharm. Bull. 34 (1986) 1128
33. Olivier, C.; Amblard, M.; Bergé, G.; Dodey, P.; Martinez, J. In Peptides 2000, Proceedings of the 26th European Peptide Symposium, 2001; pp 705-706.
34. Amblard M., Raynal N., Averlant-Petit M.-C., Didierjean C., Calmès M., Fabre O., Aubry A., Marraud M., and Martinez J. Tetrahedron Lett. 46 (2005) 3733
35. Riggs J.R., Kolesnikov A., Hendrix J., Young W.B., Shrader W.D., Vijaykumar D., Stephens R., Liu L., Pan L., Mordenti J., Green M.J., and Sukbuntherng J. Bioorg. Med. Chem. Lett. 16 (2006) 2224
36. Reeh C., Wundt J., and Clement B. J. Med. Chem. 50 (2007) 6730
37. Sanderson P.E., Cutrona K.J., Dorsey B.D., Dyer D.L., McDonough C.M., Naylor-Olsen A.M., Chen I.W., Chen Z., Cook J.J., Gardell S.J., Krueger J.A., Lewis S.D., Lin J.H., Lucas Jr. B.J., Lyle E.A., Lynch Jr. J.J., Stranieri M.T., Vastag K., Shafer J.A., and Vacca J.P. Bioorg. Med. Chem. Lett. 8 (1998) 817
38. Amblard M., Calmès M., Roques V., Tabet S., Loffet A., and Martinez J. Org. Prep. Proced. Int. 34 (2002) 405
39. Trujillo J.I., Huang H.-C., Neumann W.L., Mahoney M.W., Long S., Huang W., Garland D.J., Kusturin C., Abbas Z., South M.S., and Reitz D.B. Bioorg. Med. Chem. Lett. 17 (2007) 4568
40. Hu H., Kolesnikov A., Riggs J.R., Wesson K.E., Stephens R., Leahy E.M., Shrader W.D., Sprengeler P.A., Green M.J., Sanford E., Nguyen M., Gjerstad E., Cabuslay R., and Young W.B. Bioorg. Med. Chem. Lett. 16 (2006) 4567
41. Kadono S., Sakamoto A., Kikuchi Y., Oh-eda M., Yabuta N., Koga T., Hattori K., Shiraishi T., Haramura M., Kodama H., Esaki T., Sato H., Watanabe Y., Itoh S., Ohta M., and Kozono T. Biochem. Biophys. Res. Commun. 324 (2004) 1227
42. Paris M., Pothion C., Heitz A., Martinez J., and Fehrentz J.-A. Tetrahedron Lett. 39 (1998) 1341
43. Dubé D., and Scholte A.A. Tetrahedron Lett. 40 (1999) 2295
44. Toth G., and Köver K.E. Synth. Commun. 25 (1995) 3067
45. Monzino R., Harris S.A., Wolf D.E., Hoffhine C.E., Easton N.R., and Folkers K. J. Am. Chem. Soc. 67 (1945) 2092