Exploration of orally available calpain inhibitors. Part 3: Dipeptidyl α-ketoamide derivatives containing pyridine moiety

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 16, 2006, Pages 5691-5698

  Shirasaki, Yoshihisa ^a   Miyashita, Hiroyuki ^a   Yamaguchi, Masazumi ^a  

^a SENJU PHARMACEUTICAL CO LTD   (Japan)

Author keywords

Ketoamide; Calpain inhibitor; Oral bioavailability; Pyridineethanol; Retinal penetration; Water solubility

Indexed keywords

[1 [[[1 BENZYL 3 (CYCLOPROPYLAMINO) 2,3 DIOXOPROPYL]AMINO]CARBONYL] 3 METHYLBUTYL]CARBAMIC ACID 2 (PYRIDIN 2 YL)ETHYL ESTER; AMIDE; CALPASTATIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; AREA UNDER THE CURVE; ARTICLE; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG EFFICACY; DRUG POTENCY; DRUG SOLUBILITY; DRUG SYNTHESIS; MALE; NONHUMAN; PROTEIN DEGRADATION; RAT; RETINA;

ADMINISTRATION, ORAL; ANIMALS; BIOLOGICAL AVAILABILITY; CALPAIN; CELL DEATH; DIPEPTIDES; HUMANS; NEUROPROTECTIVE AGENTS; PYRIDINES; RATS; RATS, SPRAGUE-DAWLEY; RETINAL DEGENERATION; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP; WATER;

EID: 33745631777     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.04.013     Document Type: Article

References (45)

1. Branca D. Biochem. Biophys. Res. Commun. 322 (2004) 1098
2. Ono Y., Sorimachi H., and Suzuki K. In: Wang K.K.W., and Yuen P.-W. (Eds). Calpain: Pharmacology and Toxicology of Calcium-Dependent Protease (1999), Taylor & Francis, Philadelphia 1-3
3. Huang Y., and Wang K.K. Trends Mol. Med. 7 (2001) 355
4. Wang K.K.W., and Yuen P.-W. Trends Pharmacol. Sci. 15 (1994) 412
5. Stracher A. Ann. N.Y. Acad. Sci. 884 (1999) 52
6. Yuen P.-W., and Wang K.K.W. Exp. Opin. Invest. Drugs 5 (1996) 1291
7. Zatz M., and Starling A. N. Eng. J. Med. 352 (2005) 2413
8. Sakamoto Y., Nakajima T., Fukiage C., Sakai O., Yoshida Y., Azuma M., and Shearer T.R. Curr. Eye Res. 21 (2000) 571
9. Oka T., Tamada Y., Nakajima M., Shearer T.R., and Azuma M. J. Neurosci. Res. 83 (2006) 1342
10. Sharma A.K., and Rohrer B. J. Biol. Chem. 279 (2004) 35564
11. Paquet-Durand F., Azadi S., Hauck S.M., Ueffing M., van Veen T., and Ekstrom P. J. Neurochem. 96 (2006) 802
12. Donkor I.O. Curr. Med. Chem. 7 (2000) 1171
13. Wells G.J., and Bihovsky R. Exp. Opin. Ther. Patents 8 (1998) 1707
14. Leung D., Abbenante G., and Fairlie D.P. J. Med. Chem. 43 (2000) 305
15. Iqbal M., Messina P.A., Freed B., Das M., Chatterjee S., Tripathy R., Tao M., Josef K.A., Dembofsky B., Dunn D., Griffith E., Siman R., Senadhi S.E., Biazzo W., Bozyczko-Coyne D., Meyer S.L., Ator M.A., and Bihovsky R. Bioorg. Med. Chem. Lett. 7 (1997) 539
16. Hanada K., Tamai M., Ymagishi M., Ohmura S., Sawada J., and Tanaka I. Agric. Biol. Chem. 42 (1978) 523
17. Parkes C., Kembhavi A.A., and Barrett A.J. Biochem. J. 230 (1985) 509
18. Sasaki T., Kikuchi T., Fukui I., and Murachi T. J. Biochem. 99 (1986) 173
19. Angliker H., Anagli J., and Shaw E. J. Med. Chem. 35 (1992) 216
20. Palmer J.T., Rasnick D., Klaus J.L., and Bromme D. J. Med. Chem. 38 (1995) 3193
21. Crawford C., Mason R.W., Wikstrom P., and Shaw E. Biochem. J. 253 (1988) 751
22. Aoyagi T., Takeuchi T., Matsuzaki A., Kawamura K., and Kondo S. J. Antibiot. 22 (1969) 283
23. Sasaki T., Kishi M., Saito M., Tanaka T., Higuchi N., Kominami N., Katunuma N., and Murachi T. J. Enzyme Inhib. 3 (1990) 195
24. Li Z., Patil G.S., Golubski Z.E., Hori H., Tehrani K., Foreman J.E., Eveleth D.D., Bartus R.T., and Powers J.C. J. Med. Chem. 36 (1993) 3472
25. Li Z., Ortega-Vilain A., Patil G.S., Chu D., and Foreman J.E. J. Med. Chem. 39 (1996) 4089
26. Mehdi S. Trends Biochem. Sci. 16 (1991) 150
27. Harbeson S.L., Abelleira S.M., Akiyama A., Barrett R., Carroll R.M., Straub J.A., Tkacz J.N., Wu C., and Musso G.F. J. Med. Chem. 37 (1994) 2918
28. Ando, R.; Sasaki, T.; Masuda, H.; Inakoshi, N.; Jikihara, T.; Fujimura, Y.; Niwa, T.; Yoshii, N.; Tabata, R. PCT Int. Appl. WO9625408, 1998; Chem. Abstr. 1996, 125, 30081.
29. Nakamura M., Yamaguchi M., Sakai O., and Inoue J. Bioorg. Med. Chem. 11 (2003) 1371
30. Nakamura M., and Inoue J. Bioorg. Med. Chem. Lett. 12 (2002) 1603
31. Raghava S., Hammond M., and Kompella U.B. Expert Opin. Drug Deliv. 1 (2004) 99
32. Fukiage C., Azuma M., Nakamura Y., Tamada Y., Nakamura M., and Shearer T.R. Biochim. Biophys. Acta 1361 (1997) 304
33. Inoue J., Nakamura M., Cui Y., Sakai Y., Sakai O., Hill J.R., Wang K.K.W., and Yuen P.-W. J. Med. Chem. 46 (2003) 868
34. Kupina N.C., Nath R., Bernath E.E., Inoue J., Mitsuyoshi A., Yuen P.-W., Wang K.K.W., and Hall E.D. J. Neurotrauma 18 (2001) 1229
35. Shirasaki Y., Miyashita H., Yamaguchi M., Inoue J., and Nakamura M. Bioorg. Med. Chem. 13 (2005) 4473
36. Ano R., Kimura Y., Urakami M., Shima M., Matsuno R., Ueno T., and Akamatsu M. Bioorg. Med. Chem. 12 (2004) 249
37. Ribadeneira M.D., Aungst B.J., Eyermann C.J., and Huang S.-M. Pharm. Res. 13 (1996) 227
38. Pauletti G.M., Okumu F.W., and Borchardt R.T. Pharm. Res. 14 (1997) 164
39. Palm K., Luthman K., Ros J., Gråsjo J., and Artusson P. J. Pharmacol. Exp. Ther. 291 (1999) 435
40. Kassahun K., McIntosh I.S., Shou M., Walsh D.J., Rodeheffer C., Slaughter D.E., Geer L.A., Halpin R.A., Agrawal N., and Rodrigues A.D. Drug Metab. Dispos. 29 (2001) 813
41. Krieter P.A., Colletti A.E., Doss G.A., and Miller R.R. Drug Metab. Dispos. 22 (1994) 625
42. Riska P.S., Joseph D.P., Dinallo R.M., Davidson W.C., Keirns J.J., and Hattox S.E. Drug Metab. Dispos. 27 (1999) 1434
43. Chiba M., Jin L., Neway W., Vacca J.P., Tata J.R., Chapnman K., and Lin H.L. Drug Metab. Dispos. 29 (2001) 1
44. Hughes P.M., Olejnik O., Chang-Lin J.E., and Wilson C.G. Adv. Drug Deliv. Rev. 57 (2005) 2010
45. Meyer S.L., Bozyczko-Coyne D., Mallya S.K., Spais C.M., Bihovsky R., Kawooya J.K., Lang D.M., Scott R.W., and Siman R. Biochem. J. 314 (1996) 511