Design and synthesis of potent, orally active, inhibitors of carboxypeptidase U (TAFIa)

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 5, 2004, Pages 1151-1175

  Polla, Magnus O ^a   Tottie, Louise ^a   Nordén, Carita ^a   Linschoten, Marcel ^a,d   Müsil, Djordje ^a,e   Trumpp Kallmeyer, Susanne ^a,f   Aukrust, Inger R ^b,g   Ringom, Rune ^b,h   Holm, Kjetil H ^b   Neset, Siren M ^b   Sandberg, Marcel ^b,g   Thurmond, John ^c   Yu, Peng ^c   Hategan, Georgeta ^c   Anderson, Herb ^c  

^a ASTRAZENECA R AND D   (Sweden)

^b SINTEF   (Norway)

^c DeCODE Chemistry & Biostructures   (United States)

^d Atomos AB   (Sweden)

^e MERCK KGAA   (Germany)

^f Untere Apotheke   (Germany)

^g Synthetica AS   (Norway)

^h BIOVITRUM AB   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

PROPIONIC ACID DERIVATIVE; THROMBIN ACTIVATABLE FIBRINOLYSIS INHIBITOR;

ARTICLE; BIOAVAILABILITY; DRUG DESIGN; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS;

EID: 10744221306     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2003.12.039     Document Type: Article

References (30)

1. Hendriks D., Scharpe S., Van Sande M., Lommaert M.P. J. Clin. Chem. Clin. Biochem. 27:1989;277.
2. Bajzar L., Manuel R., Nesheim M.E. J. Biol. Chem. 270:1995;14477.
3. Campbell W., Okada H. Biochem. Biophys. Res. Commun. 162:1989;933.
4. Eaton D.L., Malloy B.E., Tsai S.P., Henzel W., Drayna D. J. Biol. Chem. 266:1991;21833.
5. Plasma carboxypeptidase B should not be confused with the related enzyme pancreatic carboxypeptidase B.
6. Bouma B.N., Marx P.F., Mosnier L.O., Meijers J.C.M. Thrombosis Research. 101:2001;329.
7. Nagashima M., Yin Z.-F., Zhao L., White K., Zhu Y., Lasky N., Halks-Miller M., Broze G.J. Jr., Fay W.P., Morser J. Journal of Clinical Investigation. 109:2002;101.
8. WO 00/66550, WO 00/66557, WO 03/013526, WO 03/027128, WO 01/19836, WO 02/14285, WO 03/061652 and WO 03/061653.
9. Redlitz A., Nicolini F.A., Malycky J.L., Topol E.J., Plow E.F. Circulation. 93:1996;1328.
10. Nagashima M., Werner M., Wang M., Zhao L., Light D.R., Pagila R., Morser J., Verhallen P. Thrombosis Research. 98:2000;333.
11. Klement P., Liao P., Bajzar L. Blood. 94:1999;2735.
12. Refino C.J., DeGuzman L., Schmitt D., Smyth R., Jeet S., Lipari M.T., Eaton D., Bunting S. Fibrinolysis & Proteolysis. 14:2000;305.
13. Hendriks D., Wang W., Scharpé S., Lommaert M.-P., van Sande M. Biochimica et Biophysica Acta. 1034:1990;86.
14. Eaton D.L., Malloy B.E., Tsai S.P., Henzel W., Drayna D. The Journal of Biological Chemistry. 266:1991;21833.
15. McKay T.J., Plummer T.H. Jr. Biochemistry. 17:1978;401.
16. Ryan T.J., Plummer T.H. Jr. Biochemical and Biophysical Research Communications. 98:1981;448.
17. Barrow J.C., Nantermet P.G., Stauffer S.R., Ngo P.L., Steinbeiser M.A., Mao S.-S., Carrol S.S., Bailey C., Colussi D., Bosserman M., Burlein C., Cook J.J., Sitko G., Tiller P.R., Miller-Stein C.M., Rose M., McMasters D.R., Vacca J.P., Selnick H.G. TAFIa inhibitors based on the imidazole acetic acid scaffold have recently been reported: J. Med. Chem. 46:2003;5294.
18. Pdb entries: 1bav, 1cbx, 1cps, 1dtd, 1f57, 1 hdq, 1 hdu, 1 hee, 2ctc, 3cpa, 4cpa, 5cpa, 6cpa, 7cpa, 8cpa.
19. Pdb entry: 1cpb.
20. Coll M., Guasch A., Aviles F.X., Huber R. EMBO J. 10:1991;1.
21. Huey R., Bloor C.M., Kawahara M.S., Hugli T.E. Am. J. Pathol. 112:1983;48.
22. Vriend G. J. Mol. Graph. 8:1990;52.
23. Ondetti M.A., Condon M.E., Reid J., Sabo E.F., Cheung H.S., Cushman D.W. Biochemistry. 18:1979;1427.
24. Pdb entry: 1cpx.
25. Ewing T.J.A., Makino S., Skillman A.G., Kuntz I.D. J. Comp.-Aided Mol. Des. 15:2001;411.
26. Jones G., Willett P., Glen R.C., Leach A.R., Taylor R. J. Mol. Biol. 267:1997;727.
27. Coll M., Guasch A., Aviles F.X., Huber R. EMBO J. 10:1991;1.
28. Melo A., Ramos M. J. Chem. Phys Lett. 245:1995;498.
29. WO 00/66152.
30. Hendriks D., Scharpé S., van Sande M. Clinical Chemistry, 1985, 31, 1936-1939; and Wang, Wei, Hendriks, Dirk, Scharpé, Simon. The Journal of Biological Chemistry. 269:1994;15937.