Tissue factor-fVIIa inhibition: Update on an unfinished quest for a novel oral antithrombotic

Drug Discovery Today

Volumn 19, Issue 9, 2014, Pages 1440-1444

  Priestley, E Scott ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTICOAGULANT AGENT; BENZAMIDINE DERIVATIVE; BLOOD CLOTTING FACTOR 7A; BLOOD CLOTTING FACTOR 7A INHIBITOR; ISOQUINOLINE DERIVATIVE; PRODRUG; SULFONAMIDE; THROMBOPLASTIN; TISSUE FACTOR COAGULATION FACTOR VIIA INHIBITOR; TISSUE FACTOR PATHWAY INHIBITOR; UNCLASSIFIED DRUG; ZWITTERIONIC ACYLSULFONAMIDE; FIBRINOLYTIC AGENT;

ANTICOAGULANT THERAPY; ANTICOAGULATION; BLOOD CLOTTING FACTOR 7 DEFICIENCY; CLINICAL TRIAL (TOPIC); COMPLEX FORMATION; DRUG BINDING; DRUG RESEARCH; DRUG TARGETING; ENZYME INHIBITION; HUMAN; IN VIVO STUDY; KNOCKOUT MOUSE; NONHUMAN; REVIEW; VALIDATION STUDY; ANIMAL; ANTAGONISTS AND INHIBITORS; DRUG DESIGN; ORAL DRUG ADMINISTRATION;

ADMINISTRATION, ORAL; ANIMALS; DRUG DESIGN; FACTOR VIIA; FIBRINOLYTIC AGENTS; HUMANS; THROMBOPLASTIN;

EID: 84907848690     PISSN: 13596446     EISSN: 18785832     Source Type: Journal    
DOI: 10.1016/j.drudis.2014.05.023     Document Type: Review

References (52)

1. R. De Caterina New oral anticoagulants in atrial fibrillation and acute coronary syndromes J. Am. Coll. Cardiol. 59 2012 1413 1425
2. L.A. Robinson, and E.M.K. Saiah Anticoagulants: inhibitors of the factor VIIa/tissue factor pathway W.J. Greenlee, Annual Reports in Medicinal Chemistry Vol. 37 2002 Elsevier Science 85 94
3. R.A. Lazarus Inhibitors of tissue factor-factor VIIa for anticoagulant therapy Curr. Med. Chem. 11 2004 2275 2290
4. R. Frederick Modulators of the coagulation cascade: focus and recent advances in inhibitors of tissue factor, factor VIIa and their complex Curr. Med. Chem. 12 2005 397 417
5. R.A. Shirk, and G.P. Vlasuk Inhibitors of factor VIIa/tissue factor Arterioscler. Thromb. Vasc. Biol. 27 2007 1895 1900
6. J.H. Morrissey Quantitation of activated factor VII levels in plasma using a tissue factor mutant selectively deficient in promoting factor VII activation Blood 81 1993 734 744
7. Y. Nemerson, and D. Repke Tissue factor accelerates the activation of coagulation factor VII: the role of a bifunctional coagulation cofactor Thromb. Res. 40 1985 351 358
8. J. Steffel Tissue factor in cardiovascular diseases: molecular mechanisms and clinical implications Circulation 113 2006 722 731
9. L.A. Harker Antithrombotic and antilesion benefits without hemorrhagic risks by inhibiting tissue factor pathway Haemostasis 26 Suppl. 1 1996 76 82
10. J. Himber Dissociation of antithrombotic effect and bleeding time prolongation in rabbits by inhibiting tissue factor function Thromb. Haemost. 78 1997 1142 1149
11. J. Himber Inhibition of arterial thrombosis by a soluble tissue factor mutant and active site-blocked factors IXa and Xa in the guinea pig Thromb. Haemost. 85 2001 475 481
12. R.F. Kelley A soluble tissue factor mutant is a selective anticoagulant and antithrombotic agent Blood 89 1997 3219 3227
13. K.G. Zbinden Dose-dependent antithrombotic activity of an orally active tissue factor/factor VIIa inhibitor without concomitant enhancement of bleeding propensity Bioorg. Med. Chem. 14 2006 5357 5369
14. W.B. Young Factor VIIa inhibitors: chemical optimization, preclinical pharmacokinetics, pharmacodynamics, and efficacy in an arterial baboon thrombosis model Bioorg. Med. Chem. Lett. 16 2006 2037 2041
15. C.S. Arnold The antithrombotic and anti-inflammatory effects of BCX-3607, a small molecule tissue factor/factor VIIa inhibitor Thromb. Res. 117 2006 343 349
16. A.G. Olivero A selective, slow binding inhibitor of factor VIIa binds to a nonstandard active site conformation and attenuates thrombus formation in vivo J. Biol. Chem. 280 2005 9160 9169
17. D. Suleymanov Osman Pharmacological interruption of acute thrombus formation with minimal hemorrhagic complications by a small molecule tissue factor/factor VIIa inhibitor: comparison to factor Xa and thrombin inhibition in a nonhuman primate thrombosis model J. Pharmacol. Exp. Ther. 306 2003 1115 1121
18. A.K. Salyers Assessment of bleeding propensity in non-human primates by combination of selective tissue factor/VIIa inhibition and aspirin compared to warfarin and aspirin treatment Pharmacology 70 2004 100 106
19. J.A. Szalony Administration of a small molecule tissue factor/factor VIIa inhibitor in a non-human primate thrombosis model of venous thrombosis: effects on thrombus formation and bleeding time Thromb. Res. 112 2003 167 174
20. E.D. Rosen Mice lacking factor VII develop normally but suffer fatal perinatal bleeding Nature 390 1997 290 294
21. E.D. Rosen Generation of genetically-altered mice producing very low levels of coagulation factor VII Thromb. Haemost. 94 2005 493 497
22. S.S. Acharya Rare bleeding disorder registry: deficiencies of factors II, V, VII, X, XIII, fibrinogen and dysfibrinogenemias J. Thromb. Haemostasis 2 2004 248 256
23. J.H. McVey Factor VII deficiency and the FVII mutation database Hum. Mutat. 17 2001 3 17
24. G.P. Vlasuk, and W.E. Rote Inhibition of factor VIIa/tissue factor with nematode anticoagulant protein c2. From unique mechanism to a promising new clinical anticoagulant Trends Cardiovasc. Med. 12 2002 325 331
25. A.H.M. Moons Recombinant nematode anticoagulant protein c2, an inhibitor of the tissue factor/factor VIIa complex, in patients undergoing elective coronary angioplasty J. Am. Coll. Cardiol. 41 2003 2147 2153
26. R.P. Giugliano Recombinant nematode anticoagulant protein c2 in patients with non-ST-segment elevation acute coronary syndrome: the ANTHEM-TIMI-32 trial J. Am. Coll. Cardiol. 49 2007 2398 2407
27. D.A. Morrow Potent inhibition of thrombin with a monoclonal antibody against tissue factor (Sunol-cH36): results of the PROXIMATE-TIMI 27 trial Eur. Heart J. 26 2005 682 688
28. A.A. Khorana Tissue factor expression, angiogenesis, and thrombosis in pancreatic cancer Clin. Cancer Res. 13 2007 2870 2875
29. R.S. Kasthuri Role of tissue factor in cancer J. Clin. Oncol. 27 2009 4834 4838
30. W.B. Young Optimization of a screening lead for factor VIIa/TF Bioorg. Med. Chem. Lett. 11 2001 2253 2256
31. W.D. Shrader Factor VIIa inhibitors: gaining selectivity within the trypsin family Bioorg. Med. Chem. Lett. 16 2006 1596 1600
32. A. Kolesnikov Factor VIIa inhibitors: improved pharmacokinetic parameters Bioorg. Med. Chem. Lett. 16 2006 2243 2246
33. K.E. Welty-Wolf Blockade of tissue factor-factor X binding attenuates sepsis-induced respiratory and renal failure Am. J. Physiol. 290 2006 L21 L31
34. P.E. Morris A Phase I study evaluating the pharmacokinetics, safety and tolerability of an antibody-based tissue factor antagonist in subjects with acute lung injury or acute respiratory distress syndrome BMC Pulm. Med. 12 2012 5
35. T. Nakabayashi Pharmacokinetics of the amidine prodrug of a novel oral anticoagulant factor VIIa inhibitor (AS1924269-00) in rats Pharmazie 68 2013 349 354
36. T. Nakabayashi Characterization of in vitro biotransformation of the new oral anticoagulants, the factor VIIa inhibitors AS1927819-00 and AS1932804-00 Pharmazie 68 2013 406 418
37. D. Vijaykumar Efforts toward oral bioavailability in factor VIIa inhibitors Bioorg. Med. Chem. Lett. 16 2006 3829 3832
38. J.R. Riggs Factor VIIa inhibitors: a prodrug strategy to improve oral bioavailability Bioorg. Med. Chem. Lett. 16 2006 2224 2228
39. K.G. Zbinden Selective and orally bioavailable phenylglycine tissue factor/factor VIIa inhibitors Bioorg. Med. Chem. Lett. 15 2005 5344 5352
40. Ishihara, T. et al. (2006) Astellas Pharma Inc. Preparation of carboxylic acid derivatives having three cyclic moieties as anticoagulants. WO2006070878
41. T. Nagakura Selective tissue factor/factor VIIa inhibitor, ER-410660, and its prodrug, E5539, have anti-venous and anti-arterial thrombotic effects with a low risk of bleeding Thromb. Res. 132 2013 271 279
42. P.C. Wong BMS-593214, an active site-directed factor VIIa inhibitor: enzyme kinetics, antithrombotic and antihemostatic studies Thromb. Haemost. 104 2010 261 269
43. P.C. Wong, and X. Jiang Apixaban, a direct factor Xa inhibitor, inhibits tissue-factor induced human platelet aggregation in vitro: comparison with direct inhibitors of factor VIIa, XIa and thrombin Thromb. Haemost. 104 2010 302 310
44. E.S. Priestley Discovery and gram-scale synthesis of BMS-593214, a potent, selective FVIIa inhibitor Bioorg. Med. Chem. Lett. 23 2013 2432 2435
45. X. Zhang Design and synthesis of bicyclic pyrazinone and pyrimidinone amides as potent TF-FVIIa inhibitors Bioorg. Med. Chem. Lett. 23 2013 1604 1607
46. M. Storgaard Design, synthesis and biological activity of novel peptidyl benzyl ketone FVIIa inhibitors Bioorg. Med. Chem. Lett. 21 2011 3918 3922
47. S.A. Bolton Discovery of nonbenzamidine factor VIIa inhibitors using a biaryl acid scaffold Bioorg. Med. Chem. Lett. 23 2013 5239 5243
48. Senokuchi, K. and Ogawa, K. (1999) Ono Pharmaceutical Co., Ltd. Preparation of amidinophenylcarbamoylbiphenyl derivatives and heterocyclic analogs thereof as inhibitors of blood coagulation factor VIIa. WO9941231
49. M. Miura Potent and selective TF/FVIIa inhibitors containing a neutral P1 ligand Bioorg. Med. Chem. 14 2006 7688 7705
50. M. Miura Design, synthesis and biological activity of selective and orally available TF/FVIIa complex inhibitors containing non-amidine P1 ligands Bioorg. Med. Chem. 15 2007 160 173
51. P.W. Glunz Nonbenzamidine acylsulfonamide tissue factor-factor VIIa inhibitors Bioorg. Med. Chem. Lett. 23 2013 5244 5248
52. X. Zhang Design and synthesis of phenylpyrrolidine phenylglycinamides as highly potent and selective TF-FVIIA inhibitors ACS Med. Chem. Lett. 5 2014 188 192