Guanylpiperidine peptidomimetics: Potent and selective bis-cation inhibitors of factor Xa

Bioorganic and Medicinal Chemistry Letters

Volumn 10, Issue 8, 2000, Pages 745-749

  Tamura, Susan Y ^a   Levy, Odile E ^a   Uong, Theresa H ^a   Reiner, John E ^a   Goldman, Erick A ^a   Ho, Jonathan Z ^a   Cohen, Cheryl R ^a   Bergum, Peter W ^a   Nutt, Ruth F ^a   Brunck, Terence K ^a   Semple, J Edward ^a  

^a Dendreon   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BLOOD CLOTTING FACTOR 10A; CATION; GUANYLPIPERIDINE DERIVATIVE; PEPTIDE DERIVATIVE; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING KINETICS; DRUG DESIGN; DRUG MECHANISM; DRUG STRUCTURE; ENZYME INHIBITION; HUMAN; INHIBITION KINETICS; PARTIAL DRUG SYNTHESIS; STRUCTURE ANALYSIS;

CATIONS; FACTOR XA; GUANINE; MOLECULAR MIMICRY; PEPTIDES; PIPERIDINES; SERINE PROTEINASE INHIBITORS;

EID: 0034678834     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(00)00105-0     Document Type: Article

References (20)

1. Coleman, R. W.; Marder, V. J.; Salzman, E. W.; Hirsch, J. In Hemostasis and Thrombosis, Basic Principles and Clinical Practice, 3rd ed.; Colman, R. W.; Hirsch, J.; Marder, V. J.; Salzman, E. W.; Eds.; J. B. Lippincott: Philadelphia, 1994; Chapters 1, 9, 57 and 80-86.
2. Vlasuk G.P. Thromb. Haemostas. 70:1993;212.
3. (a) Fevig, J. M.; Wexler, R. R. In Ann. Rep. Med. Chem. Doherty, A. M., Ed.; Academic: San Diego, 1997; Vol. 34, p 88;
4. (b) Scarborough, R. M. J. Enzyme Inhibition 1998, 14, 15.
5. (a) Padmanabhan, K.; Padmanabhan, K. P.; Tulinsky, A.; Park, C. H.; Bode, W.; Huber, R.; Blankenship, D. T.; Cardin, A. D.; Kisiel, W. J. Mol. Biol. 1993, 232, 947.
6. (b) Brandstetter, H.; Kuhne, A.; Bode, W.; Huber, R.; von der Saal, W.; Wirthensohn, K.; Engh, R. A. J. Biol. Chem. 1996, 271, 29988.
7. Abelman, M. M.; Miller, T. A.; Nutt, R. F. PCT Patent Application WO 96/19493, Chem Abstr. 1996, 125, 196382.
8. Marlowe, C. K.; Scarborough, R. M.; Laibelman, A. M.; Sinha, U.; Zhu, B.-Y. US Patent 5721214, 1998; Chem Abstr. 1998, 128, 205143.
9. Levy, O. E.; Reiner, J. R.; Semple, J. E.; Nutt, R. F.; Ripka, W. C. J. Med. Chem. 1996, 39, 4527.
10. (b) Krishnan, R.; Zhang, E.; Hakansson, K.; Arni, R. V.; Tulinsky, A.; Lim-Wilby M. S. L.; Levy, O. E.; Semple, J. E.; Brunck, T. K. Biochemistry 1998, 37, 12094.
11. 1H NMR, HPLC, TLC) materials.
12. Tamura, S. Y.; Semple, J. E.; Ardecky, R. A.; Leon, P.; Carpenter, S.; Ge, Y.; Shamblin, B. M.; Weinhouse, M. I.; Ripka, W. C.; Nutt, R. F. Tetrahedron Lett. 1996, 37, 4091.
13. (a) Kunz, H.; Pfrengle, W.; Sager, W. Tetrahedron Lett. 1989, 30, 4109.
14. (b) Kunz, H.; Pfrengel, W.; Ruck, K.; Sager, W. Synthesis 1991, 1039.
15. Kunz H., Sager W. Angew. Chem., Int. Ed. Engl. 26:1987;557.
16. Mann K.G., Jenny R.J., Krishnaswamy S. Annu. Rev. Biochem. 57:1988;915.
17. Semple J.E., Rowley D.C., Brunck T.K., Ha-Uong T., Minami N.K., Owens T.D., Tamura S.Y., Goldman E.A., Siev D.V., Ardecky R.A., Carpenter S.H., Ge Y., Richard B.M., Nolan T.G., Håkanson K., Tulinsky A., Nutt R.F., Ripka W.C. J. Med. Chem. 39:1996;4531.
18. Cheng Y., Prusoff W.H. Biochem. Pharmacology. 22:1973;3099.
19. Morrison J.F. Trends Biochem. Sci. 7:1982;102.
20. Capello M., Vlasuk G.V., Bergum P.W., Huang S., Hotez P.J. Proc. Natl. Acad. Sci. USA. 92:1995;6152.