Peptidyl α-keto thiazole as potent thrombin inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 5, 1997, Pages 533-538

  Akiyama, Yoshihisa ^a   Tsutsumi, Seiji ^a   Hatsushiba, Emiko ^a   Ohuchi, Shoukichi ^a   Okonogi, Tsuneo ^a  

^a MEIJI SEIKA KAISHA LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 (DEXTRO PHENYLALANYLPROLYLARGINYL)THIAZOLE; ARGATROBAN; ELASTASE; KALLIKREIN; PEPTIDE DERIVATIVE; PLASMIN; PROLYL ENDOPEPTIDASE; THIAZOLE DERIVATIVE; THROMBIN; THROMBIN INHIBITOR; TRYPSIN; UNCLASSIFIED DRUG; UROKINASE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BLOOD CLOTTING TIME; CONTROLLED STUDY; DRUG DESIGN; DRUG SYNTHESIS; ENZYME INHIBITION; FLUOROMETRY; IN VITRO STUDY; INTRAVENOUS DRUG ADMINISTRATION; NONHUMAN; PARTIAL THROMBOPLASTIN TIME; PROTHROMBIN TIME; RAT; STRUCTURE ACTIVITY RELATION; THROMBIN TIME;

EID: 0031552152     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00057-7     Document Type: Article

References (20)

1. 1. Stubbs, M. T.; Bode, W. Trends. Biochem. Sci. 1995, 20, 23-28.
2. 2. Tapparelli, C.; Metternich, R.; Ehrhardt, C.; Cook, N. S.; Trends. Pharmacol. Sci. 1993, 14, 366-376. Stone, S. R. Trends. Cardiovasc. Med. 1996, 5, 134-140. Edmunds, J. J.; Rapundalo, S. T. Annu. Rep. Med. Chem. 1996, 31, 51-60.
3. 2. Tapparelli, C.; Metternich, R.; Ehrhardt, C.; Cook, N. S.; Trends. Pharmacol. Sci. 1993, 14, 366-376. Stone, S. R. Trends. Cardiovasc. Med. 1996, 5, 134-140. Edmunds, J. J.; Rapundalo, S. T. Annu. Rep. Med. Chem. 1996, 31, 51-60.
4. 2. Tapparelli, C.; Metternich, R.; Ehrhardt, C.; Cook, N. S.; Trends. Pharmacol. Sci. 1993, 14, 366-376. Stone, S. R. Trends. Cardiovasc. Med. 1996, 5, 134-140. Edmunds, J. J.; Rapundalo, S. T. Annu. Rep. Med. Chem. 1996, 31, 51-60.
5. 3. Wiley, R. A.; Rich, D. H. Med. Res. Rev. 1993, 13, 327-384.
6. 4. Edwards, P. D.; Meyer, E. F., Jr.; Vijayalakshmi, J.; Tuthill, P. A.; Andisik, D. A.; Gomes, B.; Strimpler, A. J. Am. Chem. Soc. 1992, 114, 1854-1863.
7. 5. Tsutsumi, S.; Okonogi, T.; Shibahara, S.; Patchett, A. A.; Christensen, B. G.; Bioorg. Med. Chem. Lett. 1994, 4, 831-834. Tsutsumi, S.; Okonogi, T.; Shibahara, S.; Ohuchi, S.; Hatsushiba, E.;.Patchett, A. A.; Christensen, B. G. J. Med. Chem. 1994, 37, 3492-3502.
8. 5. Tsutsumi, S.; Okonogi, T.; Shibahara, S.; Patchett, A. A.; Christensen, B. G.; Bioorg. Med. Chem. Lett. 1994, 4, 831-834. Tsutsumi, S.; Okonogi, T.; Shibahara, S.; Ohuchi, S.; Hatsushiba, E.;.Patchett, A. A.; Christensen, B. G. J. Med. Chem. 1994, 37, 3492-3502.
9. 6. Meiji Seika Kaisha, Ltd. JP08020597-A
10. 7. We prepared 17 from the glutamic acid ester i by using the methods shown below. (equation presented)
11. 8. Kawabata, S.; Miura, T.; Morita, T.; Kato, H.;Fujikawa, K.; Iwanaga, S.; Takada, K.; Kimura, T.; Sakakibara, S. Eur. J. Biochem. 1988, 172, 17-25.
12. 9. Walter, R.; Simmons, W. H.; Yoshimoto, T. Molecular & Cellular Biochemistry 1980, 30, 111-127.
13. 10. Bieth, J.; Spiess, B.; Wermuth, C. G. Biochemical Medicine 1974, 11, 350-357.
14. 11. Morita, T.; Kato, H.; Iwanaga, S.; Takada, K.; Kimura, T.; Sakakibara, S. J. Biochem. 1977, 82, 1495-1498.
15. 12. Kikumoto, R.; Tamao, Y.; Tezuka, T.; Tonomura, S.; Hara, H.; Ninomiya, K.; Hijikata. A.; Okamoto, S. Biochemistry. 1984, 23, 85-90.
16. 13. Takamiya, O. Modern Medical Laboratory 1991, 19, 187-190.
17. 14. Suzuki, S. Modern Medical Laboratory 1991, 19, 191-195.
18. 15. Shuman, R. T.; Rothenberger, R. B.; Campbell, C. S.; Smith, G. F.; Gifford-Moore, D. S.; Paschal, J. W.; Gesellchen, P. D. J. Med. Chem. 1995, 38, 4446-4453.
19. 16. 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. J.; Carpenter, S. H.; e, Y.; Richard, B. M.; Nolan, T. G.; Hakanson, K.; Tulinsky, A.; Nutt, R. F.; Ripka, W. C. J. Med. Chem. 1996, 39, 4531-4536.
20. 17. Costanzo, M. J.; Maryanoff, B. E.; Hecker, L. R.; Schott, M. R.;. Yabut, S. C.; Zhang, H.-C.; Andrade-Gordon, R.; Kauffman, J. A.; Lewis, J. M.; Krishnan, R.; Tulinsky, A. J. Med. Chem. 1996, 39, 3039-3043.