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Miscellaneous

Heterocycle derivatives that inhibit Factor Xa

Pages 1361-1367 | Published online: 25 Feb 2005

Bibliography

  • VERSTRAETE M, ZOLDHELYI P: Novel antithrombotic drugs in development. Drugs (1995) 49(6):856–884.
  • VERSTRAETE M: New developments in antiplatelet and antithrombotic therapy. Eur. Heart J. (1995) 16\(Suppl. 0:16–23.
  • AL-OBEIDI F, OSTREM JA: Factor Xa inhibitors by classi-cal and combinatorial chemistry. Drug Disc. Today (1998) 3(5):223–231.
  • KAISER B: Thrombin and Factor Xa inhibitors. Drugs Fut. (1998) 23(4):423–436.
  • •A comprehensive review that discusses the pharmacology of inhibitors of thrombin and Factor Xa, along with their clinical implications.
  • VLASUK GP: Structure and functional characterization of tick anticoagulant peptide (TAP): a potent and selec-tive inhibitor of blood coagulation Factor Xa. Thromb. Haemostasis (1993) 70(1):212–216.
  • DUN WIDDIE CT, WAXMAN L, VLASUK GP, FREIDMAN PA: Purification and characterization of inhibitors of blood coagulation Factor Xa from hematophageous organisms. Methods Enzymol (1993) 223(Proteolytic En-zymes in Coagulation, Fibrinolysis and Complement Activa-tion, Pt. B):291–312.
  • CHOAY J, PETITOU M, LORMEAU JC, SINAY P, CASU B, GATTI G: Structure-activity relationships in heparin: a synthetic pentasaccharide with high affinity for anti-thrombin III and eliciting high anti-Factor Xa activity. Biochem. Biophys. Res. Commun. (1983) 116(2):492–499.
  • VAN BOECKEL CAA, PETITOU M: The characteristic AT-III binding region in heparin: an aid in the design of new synthetic antithrombotics. Angew. Chem. Int. Ed. Engl. (1993) 32(12):1671–1690.
  • OSTREM JA, AL-OBEIDI FA, SAFAR P et al.: Discovery of a novel, potent, and specific family of Factor Xa inhibi-tors via combinatorial chemistry. Biochemistry (1998) 37(01053–1059.
  • OSTREM JA, STINGER S, AL-OBEIDI F et al.: Characteriza-tion of an orally available and highly specific synthetic Factor Xa inhibitor. Thromb. Haemostasis (1995) 73 (6):1306.
  • NAGAHARA T, YOKOYAMA Y, INAMURA K et al: Dibasic(amidinoaryfipropanoic acid derivatives as novel blood coagulation Factor Xa inhibitors. J. Med. Chem. (1994) 37(8):1200–1207.
  • •Description of the discovery of the first small molecule, non-peptidic specific inhibitor of Factor Xa and a discussion of the related structure activity relationships. This is the pro-totypic compound that has led to the preparation of several second generation inhibitors described in this manuscript.
  • HARA T, YOKOYAMA A, ISHIHARA HY eta].: DX-9065a, a new synthetic, potent anticoagulant and selective in-hibitor for Factor Xa. Thromb. Haemostasis (1994) 71 (3):314–319.
  • NAGAHARA T, KATAKURA SI, YOKOYAMA Y et al: De-sign, synthesis and biological activities of orally active coagulation Factor Xa inhibitors. Eur. J. Merl. Chem. (1995) 30 (Suppl.) :139s–143s.
  • HARA T, YOKOYAMA Y, MORISHIMA Y et al.: Species dif-ferences in anticoagulant and anti-Xa activity of DX-9065a, a highly selective Factor Xa inhibitor. Thromb. Res. (1995) 80(0:99–104.
  • HARA T, YOKOYAMA A, TANABE K, ISHIHARA H, IWA-MOTO M: DX-9065a, an orally active, specific inhibitor of Factor Xa, inhibits thrombosis without affecting bleeding time in rats. Thromb. Haemostasis (1995) 74(2)635–639.
  • MORISHIMA Y, TANABE K, TERADAY Y, HARA T, KUNI-TADA S: Antithrombotic and hemorrhagic effects of DX-9065a, a direct and selective Factor Xa inhibitor. Comparison with a direct thrombin inhibitor and anti-thrombin 111-dependent anticoagulants. Thromb. Hae-mostasis (1997) 78(5):1366–1371.
  • GUILFORD WJ, SHAW KJ, DALLAS J et al.: Design, synthe-sis and biological activity of novel Factor Xa inhibitors. 1. Z,Z-substituted bis(amidinobenzilidene)cycloke-tone analogs. 215th ACS National Meeting. Dallas, USA (1998) MEDI–121.
  • BUCKMAN BO, MOHAN R, KOOVAKKAT S, LIANG A, TRINH L, MORRISSEY MM Design, synthesis, and bio-logical activity of novel purine and bicyclic Factor Xa inhibitors. Bioorg. Merl. Chem. Lett. (1998) 8(16):2235–2240.
  • SHAW KJ, GUILFORD WJ, DALLAS JL et al.:(Z,Z) -2,7-Bis(4-amidinobenzylidene) cycloheptan-1 - one: identification of a highly active inhibitor of blood coagulation Factor Xa.j Med. Chem. (1998) 41(19):3551–3556.
  • DAVEY DD, BUCKMAN BO, EAGEN K et al.: Design, syn-thesis and biological activity of novel Factor Xa inhibi-tors. 5. Optimization of the C-4 position of the 2,6-diphenoxypyridine inhibitors for oral bioavail-ability. 215th ACS National Meeting. Dallas, USA (1998) MEDI–125.
  • PHILLIPS GB, BUCKMAN BO, DAVEY DD et al: Discoveryof Is14245-[amino(imino)methyl-2-hydroxyphenoxy]-3,5-difluoro-643-, 5-dihydro- 1 -methy1-1H-imidazol-2-y0 phenoxylpyridin-4-yllIsl-methylglycine (ZK-807834): a potent, selective, and orally active inhibitor of the blood coagulation enzyme Factor Xa. J. Med. Chem. (1998) 41 (19):3557–3562.
  • •A complete description of the design and discovery of a po-tent and selective Factor Xa inhibitor that possesses limited, but significant oral activity in three animal models. This compound (ZX-807834) will be a benchmark for evaluating newly discovered Factor Xa inhibitors for further investiga-tion/development.
  • QUAN ML, PRUITT JR, ELLIS AY et al.: Bisbenzamidineisoxazoline derivatives as Factor Xa inhibitors. Bioorg. Merl. Chem. Lett. (1997) 7(20:2813–2818.
  • SATO K, KAWASAKI T, TANIUCHI Y, HIRAYAMA F, KO-SHIO H, MATSUMOTO Y: YM-60828, a novel Factor Xa inhibitor: Separation of its antithrombotic effects from its prolongation of bleeding time. Eur. J. Pharma-col. (1997) 339(2/3):141–146.
  • SATO K, KAWASAKI T, HISAMICHI N et al.: Antithrom-botic effects of YM-60828, a newly synthesized Factor Xa inhibitor, in rat thrombosis models and its effects on bleeding time. Br. J. Pharmacol. (1998) 123(1):92–96.
  • KAWASAKI T, TOMIHISA S, KAZUO S, et al.: Comparative studies of an orally-active Factor Xa inhibitor, YM-60828, with other antithrombotic agents in a rat model of arterial thrombosis. Thromb. Haemostasis (1998) 79 (2) :410–416.
  • TANIUCHI Y, SAKAI Y, HISAMICHI N, et al.: Biochemicaland pharmacological characterization of YM-60828, a newly synthesized and orally active inhibitor of hu-man Factor Xa. Thromb. Haemostasis (1998) 79(3)543–548.
  • EWING WR, CHOI YM, BECKER M, et al.: Sulfonami-dopyrrolidinones: Design, SAR and parenteral activity of a novel class of Factor Xa inhibitors. 215th ACS Na-tional Meeting, Dallas, USA (1998) MEDI–203.
  • BRANDSTETTER H, KUEHNE A, BODE W, et al: X-ray structure of active site-inhibited clotting Factor Xa. Im-plications for drug design and substrate recognition. J. Biol. Chem. (1996) 271(47)29988–29992.
  • •The first x-ray structure of Factor Xa with a small molecule inhibitor (DX-9065a) bound in the active site is described.
  • KAMATA K, KAWAMOTO H, HONMA T, IWAMA T, KIM SH: Structural basis for chemical inhibition of human blood coagulation Factor Xa. Proc. Natl. Acad. Sci. USA (1998) 95(12):6630–6635.
  • WILEY MR, FISHER MJ: Small-molecule direct thrombin inhibitors. Exp. Opin. Ther. Patents (1997) 7(11):1265–1282.
  • •An excellent review on the development of small molecule inhibitors and the problems encountered in discovering compounds with oral activity.
  • SANDERSON PEJ, CUTRONA KJ, DORSEY BD et al: L-374,087, an efficacious, orally bioavailable, pyridi-none acetamide thrombin inhibitor. Bioorg. Med. Chem. Lett. (1998) 8(7):817–822.
  • TUCKER TJ, BRADY SF, LUMMA, WC, et al: Design and synthesis of a series of potent and orally bioavailable noncovalent thrombin inhibitors that utilize nonbasic groups in the P1 position. J. Med. Chem. (1998) 41(17):3210–3219.

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