The emergence of factor Xa inhibitors for the treatment of cardiovascular diseases: a patent review

Bibliography

• Pinto DJP, Smallheer JM, Cheney DL, Factor Xa Inhibitors: next-Generation Antithrombotic Agents. J Med Chem 2010;53:6243-74
   PubMed Web of Science ®Google Scholar
• Jackson SP. Arterial thrombosis—insidious, unpredictable and deadly. Nature Medicine 2011;17:1423-36
   PubMed Web of Science ®Google Scholar
• Ansell J, Hirsh J, Hylek E, Pharmacology and management of the vitamin K antagonists: American College of Chest Physicians evidence based clinical practice guidelines (8th edition). Chest 2008;133:160S-98S
   PubMed Web of Science ®Google Scholar
• Blossom DB, Kallen AJ, Patel PR, Outbreak of adverse reactions associated with contaminated heparin. N Engl J Med 2008;359:2674-84
   PubMed Web of Science ®Google Scholar
• Lip GY, Lim HS. Atrial fibrillation and stroke prevention. Lancet Neurol 2007;6:981-93
   PubMed Web of Science ®Google Scholar
• Spyropoulos AC, Merli G. Management of venous thromboembolism in the elderly. Drugs Aging 2006;23:651-71
   PubMed Web of Science ®Google Scholar
• Wong PC, Crain EJ, Xin B, Apixaban, an oral, direct and highly selective factor Xa inhibitor: in vitro, antithrombotic and antihemostatic studies. J Thromb Haemost 2008;6:820-9
   PubMed Web of Science ®Google Scholar
• Wong PC, Crain EJ, Watson CA, Nonpeptide Factor Xa Inhibitors III: effects of DPC423, an orally-active pyrazole antithrombotic agent, on arterial thrombosis in rabbits. J Pharmacol Exp Ther 2002;303:993-1000
   PubMed Web of Science ®Google Scholar
• Brighton TA. The direct thrombin inhibitor melagatran/ximelagatran. Med J Aust 2004;18:432-7
   Google Scholar
• Fiessinger JN, Huisman MV, Davidson BL, For the THRIVE Treatment Study Investigators. Ximelagatran vs. low molecular weight heparin and warfarin for the treatment of deep vein thrombosis: randomized trial. JAMA 2005;293:681-9
   PubMed Web of Science ®Google Scholar
• Shulman S, Wahlander K, Lundstrom T, for the THRIVE III Investigators. Secondary prevention of venous thromboembolism with the direct thrombin inhibitor ximelagatran. N Engl J Med 2003;349:1713-21
   PubMed Web of Science ®Google Scholar
• Wallentin L, Wilcox RG, Weaver W, for the ESTEEM Investigators. Oral ximelagatran for secondary prophylaxis after myocardial infarction: the ESTEEM randomized controlled trial. Lancet 2003;362:789-97
   PubMed Web of Science ®Google Scholar
• Halperin JL. Ximelagatran vs warfarin for stroke prevention in patients with nonvalvular atrial fibrillation. A randomized trial. JAMA 2005;293:690-8
   PubMed Web of Science ®Google Scholar
• Eriksson BI, Dahl OE, Rosencher N, Dabigatran etexilate versus enoxaparin for prevention of venous thromboembolism after total hip replacement: a randomised, double-blind, non-inferiority trial. Lancet 2007;370:949-56
   PubMed Web of Science ®Google Scholar
• Eriksson BI, Dahl OE, Rosencher N, RE-MODEL Study Group. Oral dabigatran etexilate vs. subcutaneous enoxaparin for the prevention of venous thromboembolism after total knee replacement: the RE-MODEL randomized trial. J Thromb Haemost 2007;5:2178-85
   PubMed Web of Science ®Google Scholar
• Schulman S, Kearon C, Kakkar AK, Dabigatran versus warfarin in the treatment of acute venous thromboembolism. N Engl J Med 2009;361:2342-52
   PubMed Web of Science ®Google Scholar
• Schulman S, Kakkar AK, Schellong SM, A randomized trial of dabigatran versus warfarin in the treatment of acute venous thromboembolism (RE-COVER II). American Society of Hematology 2011 Annual Meeting; December 12, 2011; San Diego, CA. Abstract 205
   Google Scholar
• Hauel NH, Nar H, Priepke H, Structure-based design of novel potent nonpeptide thrombin inhibitor. J Med Chem 2002;45:1757-66
   PubMed Web of Science ®Google Scholar
• Connolly SJ, Ezekowitz MD, Yusuf S, for the RE-LY Steering Committee and Investigators. Dabigatran versus warfarin in patients with atrial fibrillation. N Engl J Med 2009;361:1139-51
   PubMed Web of Science ®Google Scholar
• Verheugt WA. Novel oral anticoagulants to prevent stroke in atrial fibrillation. Nat Rev Cardiol 2010;7:149-54
   PubMed Web of Science ®Google Scholar
• Eriksson BI, Borris L, Dahl OE, ODIXa-HIP Study Investigators. Oral, direct factor Xa inhibition with BAY 59-7939 For the prevention of venous thromboembolism after total hip replacement. J Thromb Haemost 2006;4:121-8
   PubMed Web of Science ®Google Scholar
• Eriksson BI, Borris L, Dahl OE, ODIXa-HIP Study Investigators. A once-daily, oral, direct factor Xa inhibitor, rivaroxaban (BAY 59-7939), for thromboprophylaxis after total hip replacement. Circulation 2006;114:2374-81
   PubMed Web of Science ®Google Scholar
• Eriksson BI, Borris L, Dahl OE, Dose-escalation study of rivaroxaban (BAY 59-7939); an oral, direct factor Xa inhibitor; for the prevention of venous thromboembolism in patients undergoing total hip replacement. Thromb Res 2007;120:685-93
   PubMed Web of Science ®Google Scholar
• Fisher WD, Eriksson BI, Bauer KA, Rivaroxaban for thromboprophylaxis after orthopedic surgery: pooled analysis of two studies. Thromb Haemost 2007;97:931-7
   PubMed Web of Science ®Google Scholar
• Turpie AG, Fisher WD, Bauer KA, ODIXa-KNEE Study Group. BAY 59-7939: an oral, direct factor Xa inhibitor for the prevention of venous thromboembolism in patients after total knee replacement. A phase II dose-ranging study. J Thromb Haemost 2005;3:2479-86
   PubMed Web of Science ®Google Scholar
• Eriksson BI, Borris LC, Friedman RJ, RECORD1 Study Group. Rivaroxaban versus enoxaparin for thromboprophylaxis after hip arthroplasty. N Engl J Med 2008;358:2765-75
   PubMed Web of Science ®Google Scholar
• Buller HR, Lensing AWA, Prins MH, Einstein-DVT Dose-Ranging Study Investigators. A dose-ranging study evaluating once-daily oral administration of the factor Xa inhibitor rivaroxaban in the treatment of patients with acute symptomatic deep vein thrombosis: the Einstein-DVT dose-ranging study. Blood 2008;112:2242-7
   PubMed Web of Science ®Google Scholar
• Patel MR, Mahaffey KW, Garg J, Rivaroxaban versus Warfarin in nonvalvular atrial fibrillation. N Engl J Med 2011;365:883-91
   PubMed Web of Science ®Google Scholar
• Mega JL, Braunwald E, Wiviott SD, Rivaroxaban in patients with a recent acute coronary syndrome. N Engl J Med 2011;366:9-19
   PubMed Web of Science ®Google Scholar
• Lassen MR, Gallus AS, Pineo GF, The ADVANCE-2 study: a randomized double-blind trial comparing apixaban with enoxaparin for thromboprophylaxis after total knee replacement. J Thromb Haemost 2009;7:LB-MO-005
   Google Scholar
• Lassen MR, Raskob GE, Gallus A, Apixaban or enoxaparin for thromboprophylaxis after knee replacement. N Engl J Med 2009;361:594-604
   PubMed Web of Science ®Google Scholar
• Lassen MR, Gallus A, Raskob GE, Apixaban versus Enoxaparin for Thromboprophylaxis after Hip Replacement. N Engl J Med 2010;63:2487-98
   Google Scholar
• Connolly SJ, Eikelboom J, Joyner C, Apixaban in patients with atrial fibrillation. N Engl J Med 2011;364:806-17
   PubMed Web of Science ®Google Scholar
• Granger CB, Alexander JH, McMurray JJV, Apixaban versus Warfarin in Patients with Atrial Fibrillation. N Engl J Med 2011;365:981-92
   PubMed Web of Science ®Google Scholar
• http://www.portola.com/Betrixaban
   Google Scholar
• Ansell J. Factor Xa or thrombin: is factor Xa a better target? J Thromb Haemost 2007;5:60-4
   PubMed Web of Science ®Google Scholar
• Turpie AG. Oral, direct factor Xa inhibitors in development for the prevention and treatment of thromboembolic diseases. Arterioscler Thromb Vasc Biol 2007;27:1238-47
   PubMed Web of Science ®Google Scholar
• Wong PC, Crain EJ, Watson CA, Favorable therapeutic index of the direct factor Xa inhibitors, apixaban and rivaroxaban, compared with the thrombin inhibitor dabigatran in rabbits. J Thromb Haemost 2009;7:1313-20
   PubMed Web of Science ®Google Scholar
• Reverter JC. Fondaparinux sodium. Drugs Today (Barc.) 2002;38:185-94
   PubMed Web of Science ®Google Scholar
• Sculpher MJ, Lozano-Ortega G, Sambrook J, Fondaparinux versus enoxaparin in non-ST-elevation acute coronary syndromes: short-term cost and long-term cost-effectiveness using data from the Fifth Organization to Assess Strategies in Acute Ischemic Syndromes Investigators (OASIS-5) trial. Am Heart J 2009;157:845-52
   PubMed Web of Science ®Google Scholar
• Peters RJG, Joyner C, Bassand JP, and OASIS-6 Investigators. The role of fondaparinux as an adjunct to thrombolytic therapy in acute myocardial infarction: a subgroup analysis of the OASIS-6 trial. Eur Heart J 2008;29:324-31
   PubMed Web of Science ®Google Scholar
• Yusuf S, Mehta SR, Chrolavicius S, Comparison of fondaparinux and enoxaparin in acute coronary syndromes. N Engl J Med 2006;354:1464-76
   PubMed Web of Science ®Google Scholar
• Straub A, Roehrig S, Hillisch A. Oral, direct thrombin and factor Xa inhibitors: the replacement for warfarin, leeches, and pig intestines? Angew Chem Int Ed 2011;50:4574-91
   PubMed Web of Science ®Google Scholar
• Lee Y-K, Player MR. Developments in Factor Xa inhibitors for the treatment of thromboembolic disorders. Med Res Rev 2011;31:202-83
   PubMed Web of Science ®Google Scholar
• Alexander D, Jeremias A. Rivaroxaban in the contemporary treatment of acute coronary syndromes. Expert Opin Investig Drugs 2011;20:849-57
   PubMed Web of Science ®Google Scholar
• Eriksson BI, Quinlan DJ, Eikelboom JW. Novel oral factor Xa and thrombin inhibitors in the management of thromboembolism. Annu Rev Med 2011;62:41-57
   PubMed Web of Science ®Google Scholar
• Casimiro-Garcia A, Dudley DA, Heemstra RJ, Progress in the discovery of FXa inhibitors. Expert Opin Ther Patents 2006;16:119-45
   Web of Science ®Google Scholar
• Modesto de Candia M, Gianfranco LG, Altomare C. Novel factor Xa inhibitors: a patent review. Expert Opin Ther Patents 2009;19:1535-80
   PubMed Web of Science ®Google Scholar
• Bayer Schering Pharma Aktiengesellschaft, Germany & Janssen Pharmaceutical N.V. Oxazolidinones for the treatment and/or prophylaxis of heart failure. WO2009074249; 2009
   Google Scholar
• Bayer Schering Pharma Aktiengesellschaft, Germany. Oxazolidinones for the treatment of chronic obstructive pulmonary disease (COPD) and/or asthma. EP2138178, WO2009156082; 2009
   Google Scholar
• Bayer Schering Pharma A.-G., Germany. Oxazolidinones for the treatment of inflammatory conditions of the gastrointestinal tract. EP2140866, Chemical Indexing Equivalent to WO2010000404; 2010
   Google Scholar
• Bayer Schering Pharma AG. New co-crystal compound of rivaroxaban and malonic acid. WO2009149851; 2009
   Google Scholar
• Apotex Pharmachem, INC. Process for the preparation of rivaroxaban and intermediates thereof. US20110034465; 2011
   Google Scholar
• KRKA NOVO MESTO DD. Process for crystallization of rivaroxaban. WO2011012321; 2011
   Google Scholar
• Ratiopharm GMBH. Pharmaceutical compositions comprising rivaroxaban. EP2308472; 2011
   Google Scholar
• Ratiopharm GMBH. Pharmaceutical composition with modified release properties useful for treating e.g. infarct, stroke and lung embolism comprises rivaroxaban, solubilizer, non-erodible polymer and pore-forming substance. WO2010017948; 2010
   Google Scholar
• Ratiopharm GMBH. Pharmaceutical compositions comprising 5-chloro-N-(((5S)-2-oxo-3-(4-(3-oxo-4-morpholinyl)-phenyl)-1,3-oxazolidin-5-yl)-methyl)-2-thiophencarboxamid. WO2010003641; 2010
   Google Scholar
• Apotex Pharmachem, INC. Polymorphic form of 5 Chloro N {[(5S) 2 oxo 3 [4(3 oxomorpholin 4 yl)phenyl]oxazolidin 5 yl]-methyl}thiophene 2 carboxamide. US20100168111; 2011
   Google Scholar
• SANDOZ AG. Method for the preparation of rivaroxaban. WO11098501A, EP2354128; 2011
   Google Scholar
• Enatia SI. Process for the preparation of rivaroxaban and intermediates thereof. WO11080341; 2011
   Google Scholar
• Bayer Pharma Aktiengesellschaft. Method for producing substituted pyridin-2-one. WO2011134963; 2011
   Google Scholar
• Bayer Healthcare AG. Substituted (oxazolidinon-5-yl-methyl)-2-thiophene-carboxamide and use thereof in the field of blood coagulation. WO2008155032; 2008
   Google Scholar
• Boehringer Ingelheim International GmbH. Substituted amides, manufacturing and use thereof as medicaments. WO2009063028; 2009
   Google Scholar
• Boehringer Ingelheim International GmbH. Substituted amides, manufacturing and use thereof as medicaments. WO2009063029; 2009
   Google Scholar
• Legochem Bioscience Co., Ltd. FXa inhibitors with cyclic amidoxime or cyclic amidrazone as P4 subunit, process for their preparations and pharmaceutical compositions and derivatives thereof. WO2010002115; 2010
   Google Scholar
• Bioscience Co., Ltd. Method for preparing(S)-5-chloro-N-({3-[4-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)phenyl]-2-oxooxazolidin-5-yl}methyl)thiophene-2-carboxamide derivatives. WO2011005028; 2011
   Google Scholar
• Green Cross Corp, S. Korea; LegoChem Bioscience Co., Ltd. Method for preparing 5-chloro-N-({(5S)-2-oxo-3-[4-(5,6-dihydro-4H-[1,2,4]triazin-1-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide derivative and intermediate used therein. WO2011005029; 2011
   Google Scholar
• Concert Pharmaceuticals, Inc. Substituted oxazolidinone derivatives. WO2009023233; 2009
   Google Scholar
• Bristol-Myers Squibb Co. & Pfizer, Inc., USA. Dosage forms of apixaban. WO2010147978; 2010
   Google Scholar
• Auspex Pharmaceuticals, Inc. Pyrazole carboxamide inhibitors of factor Xa. WO2010030983; 2010
   Google Scholar
• Protia LLC. Deuterium-enriched apixaban. US20090076069; 2009
   Google Scholar
• Daiichi Sankyo Co., Ltd. Method for producing optically active diamine derivative. WO2010104106; 2010
   Google Scholar
• Daiichi Sankyo Co., Ltd. Process to produce optically active carboxylic acid derivative. WO2010067824; 2010
   Google Scholar
• Daiichi Sankyo Co., Ltd. Activated blood coagulation factor Xa (FXa) inhibitors. WO2010071164; 2010
   Google Scholar
• Daiichi Sankyo Co., Ltd. Method for producing diamine derivative. WO2010071121; 2010
   Google Scholar
• Daiichi Sankyo Co., Ltd. Pharmacologically acceptable salt of [1,3,4]oxadiazole compound or hydrate thereof. WO2010058751; 2010
   Google Scholar
• Daiichi Sankyo Co., Ltd. Novel diamide derivative. JP2010120852L; 2010
   Google Scholar
• Portola Pharmaceuticals, Inc., USA. Antidotes for factor Xa inhibitors and methods of using the same. WO2009042962; 2009
   Google Scholar
• Portola Pharmaceuticals, Inc., USA. Antidotes for factor Xa inhibitors and methods of using the same. US20100255000; 2010
   Google Scholar
• Portola Pharmaceuticals, Inc., USA. Antidotes for factor Xa inhibitors and methods of using the same in combination with blood coagulating agents. WO2010056765; 2010
   Google Scholar
• Portola Pharmaceuticals, Inc., USA. Unit dose formulation of antidotes for factor X inhibitors and methods of using the same. WO2011008885; 2011
   Google Scholar
• Cadila Healthcare Ltd, India. Sulfoximine derivatives as factor Xa inhibitors. WO2009053999; 2010
   Google Scholar
• Tovbin, Dmitry Gennadlevich, Russian. Urethanes, ureas, amidines and related inhibitors of factor Xa. WO2011108963; 2011
   Google Scholar
• Novel acylated decasaccharides and their use as antithrombotic agents. WO2010128450; 2010
   Google Scholar
• SANOFI-AVENTIS. Novel acylated 1,6-anhydro decasaccharide and its use as antithrombotic agent. WO2010128446; 2010
   Google Scholar
• SANOFI-AVENTIS. Novel sulfated heptasaccharide and its use as antithrombotic agent. WO2010128447; 2010
   Google Scholar
• SANOFI-AVENTIS. Hexadecasaccharides with antithrombotic activity, including a covalent bond and an amino chain. WO2010023375; 2010
   Google Scholar
• SANOFI-AVENTIS. Polysaccharides with antithrombotic activity, including a covalent bond and an amino chain. WO2010023374; 2010
   Google Scholar
• United States Dept. of Health and Human Services, USA. Sand fly salivary proteins as factor Xa inhibitors and methods of use as anticoagulants. WO2010078469; 2010
   Google Scholar
• Coinfar - Consorcio de Industrias Farmaceuticas, Brazil. Kunitz-type recombinant factor. US20090042786; 2009
   Google Scholar
• Sanofi-Aventis. Chlorothiophene-amides as inhibitors of coagulation factors Xa and thrombin. WO2009103440; 2009
   Google Scholar
• Sanofi-Aventis. Chlorothiophene-isoxazoles as inhibitors of coagulation factors Xa and thrombin. WO2009103439; 2009
   Google Scholar
• Ajinomoto Co., Inc., Japan. Amidine derivatives. WO2010005087; 2010
   Google Scholar
• Univ North Carolina at Chapel hill. Enzymatic synthesis of sulfated polysaccharides without iduronic acid residues. WO2009014715; 2009
   Google Scholar
• Uchrezhdenie RAN Institut Khimii Khimicheskoi. Tekhnologii SO RAN, Russia; Uchrezhdenie RAMN. Gematologicheskii Nauchnyi Tsentr RAMN. Anticoagulant. RU2399377; 2010
   Google Scholar
• Virginia Commonwealth University, USA. Cinnamic acid-based oligomers and uses thereof. WO2010027594; 2010
   Google Scholar
• Schebo Biotech AG, Germany. Novel pharmaceuticals, method for the production thereof, and use thereof in therapy. WO2009018807; 2009
   Google Scholar