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Volumn 47, Issue 16, 2004, Pages 4089-4099

Design, synthesis, and biological activity of potent and selective inhibitors of blood coagulation factor Xa

Author keywords

[No Author keywords available]

Indexed keywords

3 [4 [5 (2,6 DIMETHYLPIPERIDIN 1 YL)PENTYL] 3 OXO 3,4 DIHYDROQUINOXOLIN 2 YL]BENZAMIDINE; ANTICOAGULANT AGENT; BENZAMIDINE DERIVATIVE; BLOOD CLOTTING FACTOR 10A; BLOOD CLOTTING FACTOR 10A ANTAGONIST; QUINOXALINE DERIVATIVE; THROMBIN; TRYPSIN; UNCLASSIFIED DRUG;

EID: 3242776164     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0497491     Document Type: Article
Times cited : (129)

References (33)
  • 1
    • 0033603813 scopus 로고    scopus 로고
    • From the Centers for Disease Control and Prevention. Decline in deaths from heart disease and stroke United States, 1900-1999
    • Anonymous. From the Centers for Disease Control and Prevention. Decline in deaths from heart disease and stroke United States, 1900-1999. JAMA, J. Am. Med. Assoc. 1999, 282, 724-726.
    • (1999) JAMA, J. Am. Med. Assoc. , vol.282 , pp. 724-726
  • 2
    • 0031801933 scopus 로고    scopus 로고
    • Syndromes of thrombosis and hypercoagulability. Congenital and acquired causes of thrombosis
    • Bick, R. L.; Kaplan, H. Syndromes of thrombosis and hypercoagulability. Congenital and acquired causes of thrombosis. Med. Clin. North Am. 1998, 82, 409-458.
    • (1998) Med. Clin. North Am. , vol.82 , pp. 409-458
    • Bick, R.L.1    Kaplan, H.2
  • 3
    • 1842853074 scopus 로고    scopus 로고
    • Highlights of latest advances in antithrombotics
    • Mousa, S. A. Highlights of latest advances in antithrombotics. Methods Mol. Med. 2004, 93, 1-7. Turpie, A. G. G. Antithrombotics and anticoagulants in coronary syndromes and stroke. Semin. Thrombosis Hemostasis 2000, 26 (Suppl. 1), 79-83. Agnelli, G.; Sonaglia, F. Perspectives on antithrombotic agents: from unfractionated heparin to new antithrombotics. Haematologica 2002, 87, 757-770.
    • (2004) Methods Mol. Med. , vol.93 , pp. 1-7
    • Mousa, S.A.1
  • 4
    • 0033821369 scopus 로고    scopus 로고
    • Antithrombotics and anticoagulants in coronary syndromes and stroke
    • Mousa, S. A. Highlights of latest advances in antithrombotics. Methods Mol. Med. 2004, 93, 1-7. Turpie, A. G. G. Antithrombotics and anticoagulants in coronary syndromes and stroke. Semin. Thrombosis Hemostasis 2000, 26 (Suppl. 1), 79-83. Agnelli, G.; Sonaglia, F. Perspectives on antithrombotic agents: from unfractionated heparin to new antithrombotics. Haematologica 2002, 87, 757-770.
    • (2000) Semin. Thrombosis Hemostasis , vol.26 , Issue.SUPPL. 1 , pp. 79-83
    • Turpie, A.G.G.1
  • 5
    • 0036073158 scopus 로고    scopus 로고
    • Perspectives on antithrombotic agents: From unfractionated heparin to new antithrombotics
    • Mousa, S. A. Highlights of latest advances in antithrombotics. Methods Mol. Med. 2004, 93, 1-7. Turpie, A. G. G. Antithrombotics and anticoagulants in coronary syndromes and stroke. Semin. Thrombosis Hemostasis 2000, 26 (Suppl. 1), 79-83. Agnelli, G.; Sonaglia, F. Perspectives on antithrombotic agents: from unfractionated heparin to new antithrombotics. Haematologica 2002, 87, 757-770.
    • (2002) Haematologica , vol.87 , pp. 757-770
    • Agnelli, G.1    Sonaglia, F.2
  • 6
    • 0001563885 scopus 로고
    • Thrombin active site inhibitors
    • Kimball, D. Thrombin active site inhibitors. Curr. Pharm. Des. 1995, 1, 441-468. Steinmetzer, T., Hauptmann, J.; Sturzebecher, J. Expert Opin. Invest. Drugs 2001, 10, 845-864.
    • (1995) Curr. Pharm. Des. , vol.1 , pp. 441-468
    • Kimball, D.1
  • 8
    • 0032831727 scopus 로고    scopus 로고
    • Progress in the design of inhibitors of coagulation factor Xa
    • Ewing, W. R.; Pauls, H. W.; Spada, A. P. Progress in the design of inhibitors of coagulation factor Xa. Drugs Future 1999, 24, 771-787. Sinha, J. Synthetic inhibitors of coagulation factor Xa. Expert Opin. Invest. Drugs 1999, 8, 567-573.
    • (1999) Drugs Future , vol.24 , pp. 771-787
    • Ewing, W.R.1    Pauls, H.W.2    Spada, A.P.3
  • 9
    • 0032949702 scopus 로고    scopus 로고
    • Synthetic inhibitors of coagulation factor Xa
    • Ewing, W. R.; Pauls, H. W.; Spada, A. P. Progress in the design of inhibitors of coagulation factor Xa. Drugs Future 1999, 24, 771-787. Sinha, J. Synthetic inhibitors of coagulation factor Xa. Expert Opin. Invest. Drugs 1999, 8, 567-573.
    • (1999) Expert Opin. Invest. Drugs , vol.8 , pp. 567-573
    • Sinha, J.1
  • 10
    • 0026713944 scopus 로고
    • Initiation and regulation of tissue factor-dependent blood coagulation
    • Rapaport, S. I.; Rao, L. V. M. Initiation and regulation of tissue factor-dependent blood coagulation. Arterioscler. Thromb. 1992, 12, 1111-1121.
    • (1992) Arterioscler. Thromb. , vol.12 , pp. 1111-1121
    • Rapaport, S.I.1    Rao, L.V.M.2
  • 12
    • 0034597606 scopus 로고    scopus 로고
    • Rational design, synthesis, and biological activity of benzoxazinones as novel Factor Xa inhibitors
    • Dudley, D. A.; Bunker, A. M.; Chi, L.; Cody, W. L.; Holland, D. R. et al. Rational Design, synthesis, and biological activity of benzoxazinones as novel Factor Xa inhibitors. J. Med. Chem. 2000, 43, 4063-4070.
    • (2000) J. Med. Chem. , vol.43 , pp. 4063-4070
    • Dudley, D.A.1    Bunker, A.M.2    Chi, L.3    Cody, W.L.4    Holland, D.R.5
  • 13
    • 0017611813 scopus 로고
    • Inhibition of serine proteinases by benzamidine derivatives
    • Walsmann, P. Inhibition of serine proteinases by benzamidine derivatives. Acta Biol. Med. Ger. 1977, 36, 1931-1937. Phillips, G. B., Buckman, B. O., Davey, D. D. Eagen, K. A., Guilford, W. J. et al. Discovery of N-[2-[5-amino(imino)methyl]-2-hydro-1-methyl-(1H-imidazol-2-yl)) phenoxylpyridin-4-yl]-N-methylglycine (ZK-807834): A potent and orally active inhibitor of the blood coagulation enzyme factor Xa. J. Med. Chem. 1998, 41, 3557-3562.
    • (1977) Acta Biol. Med. Ger. , vol.36 , pp. 1931-1937
    • Walsmann, P.1
  • 14
    • 0032505156 scopus 로고    scopus 로고
    • Discovery of N-[2-[5-amino(imino)methyl]-2-hydro-1-methyl-(1H-imidazol-2- yl))phenoxylpyridin-4-yl]-N-methylglycine (ZK-807834): A potent and orally active inhibitor of the blood coagulation enzyme factor Xa
    • Walsmann, P. Inhibition of serine proteinases by benzamidine derivatives. Acta Biol. Med. Ger. 1977, 36, 1931-1937. Phillips, G. B., Buckman, B. O., Davey, D. D. Eagen, K. A., Guilford, W. J. et al. Discovery of N-[2-[5-amino(imino)methyl]-2-hydro-1-methyl-(1H-imidazol-2-yl)) phenoxylpyridin-4-yl]-N-methylglycine (ZK-807834): A potent and orally active inhibitor of the blood coagulation enzyme factor Xa. J. Med. Chem. 1998, 41, 3557-3562.
    • (1998) J. Med. Chem. , vol.41 , pp. 3557-3562
    • Phillips, G.B.1    Buckman, B.O.2    Davey, D.D.3    Eagen, K.A.4    Guilford, W.J.5
  • 15
    • 3242743210 scopus 로고    scopus 로고
    • Preparation of benzoxazinones and -thiazinones as serine protease inhibitors. PCT Int. Appl.; (Warner-Lambert Company, USA).: WO 9250257, 1999
    • Berryman, K. A.; Downing, D. M.; Dudley, D. A.; Edmunds, J. J.; Narasimhan, L. S. et al. Preparation of benzoxazinones and -thiazinones as serine protease inhibitors. PCT Int. Appl.; (Warner-Lambert Company, USA).: WO 9250257, 1999; Downing, D. M., Berryman, K. A., Dudley, D. A., Zhu, Z., Pamment, M. et al. Chiral benzoxazinones as potent and selective FXa inhibitors. J. Org. Chem. 2004, submitted.
    • Berryman, K.A.1    Downing, D.M.2    Dudley, D.A.3    Edmunds, J.J.4    Narasimhan, L.S.5
  • 16
    • 3242773211 scopus 로고    scopus 로고
    • Chiral benzoxazinones as potent and selective FXa inhibitors
    • submitted
    • Berryman, K. A.; Downing, D. M.; Dudley, D. A.; Edmunds, J. J.; Narasimhan, L. S. et al. Preparation of benzoxazinones and -thiazinones as serine protease inhibitors. PCT Int. Appl.; (Warner-Lambert Company, USA).: WO 9250257, 1999; Downing, D. M., Berryman, K. A., Dudley, D. A., Zhu, Z., Pamment, M. et al. Chiral benzoxazinones as potent and selective FXa inhibitors. J. Org. Chem. 2004, submitted.
    • (2004) J. Org. Chem.
    • Downing, D.M.1    Berryman, K.A.2    Dudley, D.A.3    Zhu, Z.4    Pamment, M.5
  • 17
    • 0001233430 scopus 로고
    • Reductive addition of polyhalomethanes and their related compounds to aldehydes and 1,2-elimination of the coupling products in a palladium/aluminum bimetal redox system
    • Tanaka, H.; Yamashita, S.; Yamanoue, M.; Torii, S. Reductive addition of polyhalomethanes and their related compounds to aldehydes and 1,2-elimination of the coupling products in a palladium/aluminum bimetal redox system. J. Org. Chem. 1989, 54, 444-450.
    • (1989) J. Org. Chem. , vol.54 , pp. 444-450
    • Tanaka, H.1    Yamashita, S.2    Yamanoue, M.3    Torii, S.4
  • 18
    • 0007293082 scopus 로고
    • Investigations in the field of (trihalomethyl) carbinols. IV. Block-addition reaction of aromatic 1,4-dinucleophiles to gem-dichloro epoxides generated from aryl(trichloromethyl)carbinols
    • Gukasyan, A. K.; Galstyan, L. K.; Avetisyan, A. A. Investigations in the field of (trihalomethyl) carbinols. IV. Block-addition reaction of aromatic 1,4-dinucleophiles to gem-dichloro epoxides generated from aryl(trichloromethyl) carbinols. Arm. Khim. Zh. 1988, 41, 572-575.
    • (1988) Arm. Khim. Zh. , vol.41 , pp. 572-575
    • Gukasyan, A.K.1    Galstyan, L.K.2    Avetisyan, A.A.3
  • 19
    • 0009753431 scopus 로고
    • Advances in chemistry of amidines
    • Granik, V. G. Advances in chemistry of amidines. Usp. Khim. 1983 52, 669-703.
    • (1983) Usp. Khim. , vol.52 , pp. 669-703
    • Granik, V.G.1
  • 20
    • 0000455369 scopus 로고
    • Amidines and N-substituted amidines
    • Dunn, P. J. Amidines and N-substituted amidines. Compr. Org. Funct. Group Transform. 1995, 5, 741-782, 1161-1308.
    • (1995) Compr. Org. Funct. Group Transform. , vol.5 , pp. 741-782
    • Dunn, P.J.1
  • 22
    • 0003325707 scopus 로고
    • A high-yield modification of the Pschorr phenanthrene synthesis
    • Duclos, R. I., Jr.; Tung, J. S.; Rapoport, H. A high-yield modification of the Pschorr phenanthrene synthesis. J. Org. Chem. 1984, 49, 5243-5246.
    • (1984) J. Org. Chem. , vol.49 , pp. 5243-5246
    • Duclos Jr., R.I.1    Tung, J.S.2    Rapoport, H.3
  • 23
    • 0029143854 scopus 로고
    • An improved procedure for the cyanation of aryl trifiates: A convenient synthesis of 6-cyano-1,2,3,4-tetrahydroisoquinoline
    • Selnick, H. G.; Smith, G. R.; Tebben, A. J. An improved procedure for the cyanation of aryl trifiates: a convenient synthesis of 6-cyano-1,2,3,4- tetrahydroisoquinoline. Synth. Commun. 1995, 25, 3255-3261.
    • (1995) Synth. Commun. , vol.25 , pp. 3255-3261
    • Selnick, H.G.1    Smith, G.R.2    Tebben, A.J.3
  • 24
    • 0038305874 scopus 로고    scopus 로고
    • A convenient synthesis of two new indoloquinoline alkaloids
    • Timari, G.; Soos, T.; Hajos, G. A convenient synthesis of two new indoloquinoline alkaloids. Synlett 1997, 1067-1068.
    • (1997) Synlett , pp. 1067-1068
    • Timari, G.1    Soos, T.2    Hajos, G.3
  • 25
    • 2042507954 scopus 로고
    • Palladium-catalyzed cross-coupling reactions of organoboron compounds
    • Miyaura, N.; Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem. Rev. (Washington, D. C.) 1995, 95, 2457-2483.
    • (1995) Chem. Rev. (Washington, D. C.) , vol.95 , pp. 2457-2483
    • Miyaura, N.1    Suzuki, A.2
  • 26
    • 0021819905 scopus 로고
    • The syntheses of the corticoid side chain. I. An improved method for the preparation of 17.alpha.-hydroxyprogesterone from androst-4-ene-3, 17-dione
    • Nitta, I.; Fujimori, S.; Ueno, H. The syntheses of the corticoid side chain. I. An improved method for the preparation of 17.alpha.- hydroxyprogesterone from androst-4-ene-3, 17-dione. Bull. Chem. Soc. Jpn. 1985, 58, 978-980.
    • (1985) Bull. Chem. Soc. Jpn. , vol.58 , pp. 978-980
    • Nitta, I.1    Fujimori, S.2    Ueno, H.3
  • 28
    • 0032997963 scopus 로고    scopus 로고
    • Antithrombotic effects of BCH 2763, a new direct thrombin inhibitor, in a canine model of venous thrombosis
    • McClanahan, T. B.; Ignasiak, D. P.; Juneau, P.; Finkle, C.; Winocour, P. D. et al. Antithrombotic effects of BCH 2763, a new direct thrombin inhibitor, in a canine model of venous thrombosis. J. Thromb. Thrombolysis 1999, 7, 301-306; Ignasiak, D. P.; McClanahan, T. B.; Bousley, R. E.; Juneau, P. L.; Gallagher, K. P. Effects of intravenous enoxaparin and intravenous inogatran in an electrolytic injury model of venous thrombosis in the dog. J. Thromb. Thrombolysis 1998, 6, 199-206.
    • (1999) J. Thromb. Thrombolysis , vol.7 , pp. 301-306
    • McClanahan, T.B.1    Ignasiak, D.P.2    Juneau, P.3    Finkle, C.4    Winocour, P.D.5
  • 29
    • 0032423061 scopus 로고    scopus 로고
    • Effects of intravenous enoxaparin and intravenous inogatran in an electrolytic injury model of venous thrombosis in the dog
    • McClanahan, T. B.; Ignasiak, D. P.; Juneau, P.; Finkle, C.; Winocour, P. D. et al. Antithrombotic effects of BCH 2763, a new direct thrombin inhibitor, in a canine model of venous thrombosis. J. Thromb. Thrombolysis 1999, 7, 301-306; Ignasiak, D. P.; McClanahan, T. B.; Bousley, R. E.; Juneau, P. L.; Gallagher, K. P. Effects of intravenous enoxaparin and intravenous inogatran in an electrolytic injury model of venous thrombosis in the dog. J. Thromb. Thrombolysis 1998, 6, 199-206.
    • (1998) J. Thromb. Thrombolysis , vol.6 , pp. 199-206
    • Ignasiak, D.P.1    McClanahan, T.B.2    Bousley, R.E.3    Juneau, P.L.4    Gallagher, K.P.5
  • 30
    • 0015417053 scopus 로고
    • A manual method for applying the hansch approach to drug design
    • Topliss, J. G. A manual method for applying the hansch approach to drug design. Med. Chem. Proc. Int. Symp. 5th 1977, 421-426. Topliss, J. G. Utilization of operational schemes for analogue synthesis in drug design. J. Med. Chem. 1972, 15, 1006-1011.
    • (1977) Med. Chem. Proc. Int. Symp. 5th , pp. 421-426
    • Topliss, J.G.1
  • 31
    • 0015417053 scopus 로고
    • Utilization of operational schemes for analogue synthesis in drug design
    • Topliss, J. G. A manual method for applying the hansch approach to drug design. Med. Chem. Proc. Int. Symp. 5th 1977, 421-426. Topliss, J. G. Utilization of operational schemes for analogue synthesis in drug design. J. Med. Chem. 1972, 15, 1006-1011.
    • (1972) J. Med. Chem. , vol.15 , pp. 1006-1011
    • Topliss, J.G.1
  • 32
    • 0016796849 scopus 로고
    • The refined crystal structure of bovine beta-trypsin at 1.8 A resolution. II. Crystallographic refinement, calcium binding site, benzamidine binding site and active site at pH 7.0
    • Bode, W.; Schwager, P. The refined crystal structure of bovine beta-trypsin at 1.8 A resolution. II. Crystallographic refinement, calcium binding site, benzamidine binding site and active site at pH 7.0. J. Mol. Biol. 1975, 98, 693-717.
    • (1975) J. Mol. Biol. , vol.98 , pp. 693-717
    • Bode, W.1    Schwager, P.2


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