Design, synthesis and structure-activity relationships of benzoxazinone-based factor Xa inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 3, 2003, Pages 561-566

  Huang, Wenrong ^a   Zhang, Penglie ^a   Zuckett, Jingmei F ^a   Wang, Lingyan ^a   Woolfrey, John ^a   Song, Yonghong ^a   Jia, Zhaozhong J ^a   Clizbe, Lane A ^a   Su, Ting ^a   Tran, Katherine ^a   Huang, Brian ^a   Wong, Paul ^a   Sinha, Uma ^a   Park, Gary ^a   Reed, Andrea ^a   Malinowski, John ^a   Hollenbach, Stanley J ^a   Scarborough, Robert M ^a   Zhu, Bing Yan ^a  

^a MILLENNIUM PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

[N [4 [(1 ACETIMIDOYL 4 PIPERIDYL)OXY]PHENYL] N [(7 AMIDINO 2 NAPHTHYL)METHYL]SULFAMOYL]ACETIC ACID; ANILINE DERIVATIVE; BENZOXAZINONE DERIVATIVE; BLOOD CLOTTING FACTOR 10A INHIBITOR; INDOLE DERIVATIVE; TRYPSIN;

ANTICOAGULATION; ARTICLE; CONTROLLED STUDY; CYCLIZATION; DOSE RESPONSE; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG DESIGN; DRUG POTENCY; DRUG SYNTHESIS; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANILINE COMPOUNDS; ANIMALS; BINDING, COMPETITIVE; CRYSTALLOGRAPHY, X-RAY; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; FACTOR XA; INDICATORS AND REAGENTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; OXAZINES; RABBITS; STRUCTURE-ACTIVITY RELATIONSHIP; THROMBIN; TRYPSIN INHIBITORS;

EID: 0037330363     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(02)00927-7     Document Type: Article

References (20)

1. Davie E.W., Fujikawa K., Kisiel W. Biochemistry. 30:1991;10363.
2. (a) Scarborough R.M. J. Enz. Inhib. 14:1998;15.
3. (b) Zhu B.-Y., Scarborough R.M. Curr. Opin. Cardiov. Pulmon. Ren. Investig. Drugs. 1:1999;63.
4. (c) Zhu B.-Y., Scarborough R.M. Annu. Rep. Med. Chem. 35:2000;83.
5. Nagahara T., Yokoyama Y., Inamura K., Katakura S., Komoriya S., Yamaguchi H., Hara T., Iwamoto M. J. Med. Chem. 37:1994;1200.
6. Hirayama, F.; Koshio, H.; Taniuchi, Y.; Sato, K.; Hisamichi, N.; Sakai, Y.; Katayama, N.; Kurihara, H.; Kawasaki, T. 214th National Meeting of the American Chemical Society, Las Vegas, NV, Sept. 7-11, 1997; American Chemical Society: Washington, DC, 1997; MEDI-049.
7. Brandstetter H., Kuhne A., Bode W., Huber R., von der Saal W., Wirthensohn K., Engh R.A. J. Biol. Chem. 271:1996;2998.
8. For preliminary accounts of our studies on factor Xa inhibitors with a bicyclic template: Zhu, B. Y.; Li, W.; Huang, W.; Kane-Maguire, K.; Marlowe, C. K.; Song, Y.; Zhang, P.; Wang, L.; Fan, J.; Wong, P.; Tran, K.; Sinha, U.; Xing, L.; Scarborough, R. M. 219th National Meeting of the American Chemical Society, San Francisco, CA, March 26-30, 2000; American Chemical Society: Washington, DC, 2000; ORGN-237.
9. (a) For other studies on factor Xa inhibitors with a bicyclic template: Buckman B.O., Mohan R., Koovakkat S.K., Liang A., Morrissey M.M. Bioorg. Med. Chem. Lett. 8:1998;2235 (b) Arnaiz D.O., Zhao Z., Liang A., Trinh L., Witlow M., Koovakkat S.K., Shaw K. J. Bioorg. Med. Chem. Lett. 10:2000;957 (c) Zhao Z., Arnaiz D.O., Griedel B., Sakata S., Dallas J.L., Witlow M., Trinh L., Post J., Liang A., Morrissey M.M., Shaw K. J. Bioorg. Med. Chem. Lett. 10:2000;963 (d) Shaw K.J., Guilford W.J., Griedel B.D., Sakata S., Trinh L., Wu S., Xu W., Zhao Z., Morrissey M.M. Bioorg. Med. Chem. Lett. 12:2002;1311.
10. (a) For other studies on factor Xa inhibitors with a bicyclic template: Buckman B.O., Mohan R., Koovakkat S.K., Liang A., Morrissey M.M. Bioorg. Med. Chem. Lett. 8:1998;2235 (b) Arnaiz D.O., Zhao Z., Liang A., Trinh L., Witlow M., Koovakkat S.K., Shaw K. J. Bioorg. Med. Chem. Lett. 10:2000;957 (c) Zhao Z., Arnaiz D.O., Griedel B., Sakata S., Dallas J.L., Witlow M., Trinh L., Post J., Liang A., Morrissey M.M., Shaw K. J. Bioorg. Med. Chem. Lett. 10:2000;963 (d) Shaw K.J., Guilford W.J., Griedel B.D., Sakata S., Trinh L., Wu S., Xu W., Zhao Z., Morrissey M.M. Bioorg. Med. Chem. Lett. 12:2002;1311.
11. (a) For other studies on factor Xa inhibitors with a bicyclic template: Buckman B.O., Mohan R., Koovakkat S.K., Liang A., Morrissey M.M. Bioorg. Med. Chem. Lett. 8:1998;2235 (b) Arnaiz D.O., Zhao Z., Liang A., Trinh L., Witlow M., Koovakkat S.K., Shaw K. J. Bioorg. Med. Chem. Lett. 10:2000;957 (c) Zhao Z., Arnaiz D.O., Griedel B., Sakata S., Dallas J.L., Witlow M., Trinh L., Post J., Liang A., Morrissey M.M., Shaw K. J. Bioorg. Med. Chem. Lett. 10:2000;963 (d) Shaw K.J., Guilford W.J., Griedel B.D., Sakata S., Trinh L., Wu S., Xu W., Zhao Z., Morrissey M.M. Bioorg. Med. Chem. Lett. 12:2002;1311.
12. (a) For other studies on factor Xa inhibitors with a bicyclic template: Buckman B.O., Mohan R., Koovakkat S.K., Liang A., Morrissey M.M. Bioorg. Med. Chem. Lett. 8:1998;2235 (b) Arnaiz D.O., Zhao Z., Liang A., Trinh L., Witlow M., Koovakkat S.K., Shaw K. J. Bioorg. Med. Chem. Lett. 10:2000;957 (c) Zhao Z., Arnaiz D.O., Griedel B., Sakata S., Dallas J.L., Witlow M., Trinh L., Post J., Liang A., Morrissey M.M., Shaw K. J. Bioorg. Med. Chem. Lett. 10:2000;963 (d) Shaw K.J., Guilford W.J., Griedel B.D., Sakata S., Trinh L., Wu S., Xu W., Zhao Z., Morrissey M.M. Bioorg. Med. Chem. Lett. 12:2002;1311.
13. Kamata K., Kawamoto H., Honma T., Iwama T., Kim S.-H. Proc. Natl. Acad. Sci. U.S.A. 95:1998;6630.
14. Pruitt J.R., Pinto D.J., Estrella M.J., Bostrom L.L., Knabb R.M., Wong P.C., Wright M.R., Wexler R.R. Bioorg. Med. Chem. Lett. 10:2000;685.
15. Pinto D.J., Orwat M.J., Wang S., Fevig J.M., Quan M.L., Amparo E.C., Cacciola J., Rossi K.A., Alexander R.S., Smallwood A.S., Luettgen J.M., Liang L., Aungst B.J., Wright M.R., Knabb R.M., Wong P.C., Wexler R.R., Lam P.Y.S. J. Med. Chem. 44:2001;566.
16. Quan M.L., Liauw A.Y., Ellis C.D., Pruitt J.R., Carini D.J., Bostrom L.L., Huang P.P., Harrison K., Knabb R.M., Thoolen M.J., Wong P.C., Wexler R.R. J. Med. Chem. 42:1999;2752.
17. Takayanagi, M.; Sagi, K.; Nakagawa, T.; Yamanashi, M.; Karahara, T.; Takehana, S.; Fukuda, Y.; Takahashi, M.; Shoji, M. WO, 09831661, 1998.
18. Jones G., Willett P., Glen R.C., Leach A.R., Taylor R. J. Mol. Biol. 267:1997;727.
19. Hollenbach S., Sinha U., Lin P.H., Needham K., Frey L., Hancock T.E., Wong A., Wolf D.L. Thromb. Haemost. 71:1994;357.
20. Choi-Sledeski Y.M., Becker M.R., Green D.M., Davis R., Ewing W.R., Mason H.J., Ly C., Spada A., Liang G., Cheney D., Barton J., Chu V., Brown K., Colussi D., Bentley R., Leadley R.J., Dunwiddie C., Pauls H.W. Bioorg. Med. Chem. Lett. 9:1999;2539.