Synthesis and discovery of 2,3-dihydro-3,8-diphenylbenzo[1,4]oxazines as a novel class of potent cholesteryl ester transfer protein inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 4, 2010, Pages 1432-1435

  Wang, Aihua ^a   Prouty, Catherine P ^a   Pelton, Patricia D ^a   Yong, Maria ^a   Demarest, Keith T ^a   Murray, William V ^a   Kuo, Gee Hong ^a  

^a JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

Atherosclerosis; CETP; CETP inhibitors; Cholesteryl ester transfer protein; HDL C

Indexed keywords

2,3 DIHYDRO 3,8 DIPHENYLBENZO[1,4]OXAZINE DERIVATIVE; CHOLESTEROL ESTER TRANSFER PROTEIN INHIBITOR; HIGH DENSITY LIPOPROTEIN CHOLESTEROL; UNCLASSIFIED DRUG;

ALKYLATION; ANIMAL EXPERIMENT; AREA UNDER THE CURVE; ARTICLE; BROMINATION; CHIRALITY; CHOLESTEROL BLOOD LEVEL; CONTROLLED STUDY; DISTRIBUTION VOLUME; DRUG BIOAVAILABILITY; DRUG HALF LIFE; DRUG INHIBITION; DRUG SYNTHESIS; ENANTIOSELECTIVITY; FEMALE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; IC 50; LIVER MICROSOME; MALE; METHYLATION; MOUSE; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION; TIME TO MAXIMUM PLASMA CONCENTRATION;

ADMINISTRATION, ORAL; ANIMALS; BENZOXAZINES; CHOLESTEROL ESTER TRANSFER PROTEINS; CRICETINAE; DRUG DESIGN; ENZYME INHIBITORS; FEMALE; HUMANS; INHIBITORY CONCENTRATION 50; MALE; MICE; MICE, TRANSGENIC; MOLECULAR STRUCTURE; RATS;

CRICETINAE; MUS MUSCULUS; RATTUS;

EID: 75749090371     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.12.096     Document Type: Article

References (26)

1. Assmann G., Schulte H., von Eckardstein A., and Huang Y. Atherosclerosis 124 (1996) S11
2. Castelli W.P., Garrison R.J., Wilson P.W., Abbott R.D., Kalousdian S., and Kannel W.B. J. Am. Med. Assoc. 256 (1986) 2835
3. Kannel W.B. Am. J. Cardiol. 76 (1995) 69C
4. Bruce C., Chouinard Jr. R.A., and Tall A.R. Annu. Rev. Nutr. 18 (1998) 297
5. Yamashita S., Sakai N., Hirano K.-I., Ishigami M., Maruyama T., Nakajima N., and Matsuzawa Y. Front. Biosci 6 (2001) D366
6. Krause B.R., and Auerbach B.J. Curr. Opin. Invest. Drugs 2 (2001) 375
7. Assmann G., and Nofer J.R. Annu. Rev. Med. 54 (2003) 321
8. Tall A.R. J. Lipid Res. 34 (1993) 1255
9. Lagrost L. Biochem. Biophys. Acta 1215 (1994) 209
10. Fielding C.J., and Havel R.J. J. Clin. Invest. 97 (1996) 2687
11. Hayek T., Masucci-Magoulas L., and Jiang X. J. Clin. Invest. 96 (1995) 2071
12. Zhong S., Sharp D.S., Grove J.S., Bruce C., Yano K., Curb J.D., and Tall A.R. J. Clin. Invest. 97 (1996) 2917
13. Sikorski J.A., and Connolly D.T. Curr. Opin. Drug Discovery Dev. 4 (2001) 602
14. Shinkai H., Maeda K., Yamasaki T., Okamoto H., and Uchida I. J. Med. Chem. 43 (2000) 3566
15. Kontush A., Guerin M., and Chapman M.J. Nat. Clin. Pract. Cardiovasc. Med. 5 (2008) 329
16. Brousseau M.E., Schaefer E.J., Wolfe M.L., Bloedon L.T., Digenio A.G., Clark R.W., Mancuso J.P., and Rader D.J. N. Eng. J. Med. 350 (2004) 1505
17. Clark R.W., Ruggeri R.B., Cunningham D., and Bamberger M.J. J. Lipid Res. 4 (2006) 537
18. Barter P.J., Caulfield M., Eriksson M., Grundy S.M., Kastelein J.J.P., Komajda M., Lopez-Sendon J., Mosca L., Tardif J.C., Waters D.D., Shear C.L., Revkin J.H., Buhr K., Fisher M.R., Tall A.R., and Brewer B. N. Eng. J. Med. 357 (2007) 2109
19. Vergeer M., and Kastelein J.J.P. Nat. Clin. Pract. Cardiovasc. Med. 5 (2008) 302
20. Kuo G.-H., Rano T., Pelton P., Demarest K.T., Gibbs A.C., Murray W.V., Damiano B.P., and Connelly M.A. J. Med. Chem. 52 (2009) 1768
21. Rano T.A., Sieber-McMaster E., Pelton P.D., Yang M., Demarest K.T., and Kuo G.-H. Bioorg. Med. Chem. Lett. 19 (2009) 2456
22. Kuo, G.-H.; Wang, A.; Rano, T.; Prouty, C.; Demarest, K. T.; Pelton, P. U.S. Pat. Appl. Publ. US 2007265252 A1 20071115, 2007.
23. Sorgi, K. L.; Liu, F.; Chen, Y.; Chen, H.; Patel, M. N.; Li, X.; Wang, A.; Ballentine, S. A.; Beauchamp, D. A.; Macphee, J.-M.; Rammeloo, T. J. L.; Vanhoegaerden, T. J. PCT Int. Appl. WO 2008141077 A1 20081120, 2008.
24. Reinhard E.J., Wang J.L., Durley R.C., Fobian Y.M., Grapperhaus M.L., Hickory B.S., Massa M.A., Norton M.B., Promo M.A., Tollefson M.B., Vernier W.F., Connolly D.T., Witherbee B.J., Melton M.A., Regina K.J., Smith M.E., and Sikorski J.A. J. Med. Chem. 46 (2003) 2152
25. Atarashi S., Tsurumi H., Fujiwara T., and Hayakawa I. J. Heterocycl. Chem. 28 (1991) 329
26. Speckamp W.N., and Moolenaar M.J. Tetrahedron 56 (2000) 3817