Synthesis and structure-activity relationship of potent, selective and orally active anthranilamide-based factor Xa inhibitors: application of weakly basic sulfoximine group as novel S4 binding element.

[1]  K. Mori,et al.  Discovery of N-[2-hydroxy-6-(4-methoxybenzamido)phenyl]-4- (4-methyl-1,4-diazepan-1-yl)benzamide (darexaban, YM150) as a potent and orally available factor Xa inhibitor. , 2011, Journal of medicinal chemistry.

[2]  G. Lippi,et al.  Arterial thrombus formation in cardiovascular disease , 2011, Nature Reviews Cardiology.

[3]  S. Berkowitz,et al.  The discovery and development of rivaroxaban , 2011, Annals of the New York Academy of Sciences.

[4]  D. Kubitza,et al.  The discovery and development of rivaroxaban, an oral, direct factor Xa inhibitor , 2011, Nature Reviews Drug Discovery.

[5]  P. Sanders,et al.  New-onset atrial fibrillation and acute coronary syndrome , 2010, Expert review of cardiovascular therapy.

[6]  D. Cheney,et al.  Factor Xa inhibitors: next-generation antithrombotic agents. , 2010, Journal of medicinal chemistry.

[7]  K. Aertgeerts,et al.  Discovery of a tetrahydropyrimidin-2(1H)-one derivative (TAK-442) as a potent, selective, and orally active factor Xa inhibitor. , 2009, Journal of medicinal chemistry.

[8]  Lingyan Wang,et al.  Discovery of betrixaban (PRT054021), N-(5-chloropyridin-2-yl)-2-(4-(N,N-dimethylcarbamimidoyl)benzamido)-5-methoxybenzamide, a highly potent, selective, and orally efficacious factor Xa inhibitor. , 2009, Bioorganic & medicinal chemistry letters.

[9]  M. Gent,et al.  A randomized evaluation of betrixaban, an oral factor Xa inhibitor, for prevention of thromboembolic events after total knee replacement (EXPERT) , 2008, Thrombosis and Haemostasis.

[10]  T. Shibano,et al.  DU‐176b, a potent and orally active factor Xa inhibitor: in vitro and in vivo pharmacological profiles , 2008, Journal of thrombosis and haemostasis : JTH.

[11]  Tsutomu Nagata,et al.  Stereoselective synthesis and biological evaluation of 3,4-diaminocyclohexanecarboxylic acid derivatives as factor Xa inhibitors. , 2008, Bioorganic & Medicinal Chemistry Letters.

[12]  Chong-Hwan Chang,et al.  Structure-activity relationships of anthranilamide-based factor Xa inhibitors containing piperidinone and pyridinone P4 moieties. , 2008, Bioorganic & medicinal chemistry letters.

[13]  N. Mackman Triggers, targets and treatments for thrombosis , 2008, Nature.

[14]  Angela Smallwood,et al.  Discovery of 1-(4-methoxyphenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide (apixaban, BMS-562247), a highly potent, selective, efficacious, and orally bioavailable inhibitor of blood coagulation factor Xa. , 2007, Journal of medicinal chemistry.

[15]  E. Oger,et al.  Venous thromboembolism (VTE) in Europe , 2007, Thrombosis and Haemostasis.

[16]  J. A. Kyle,et al.  Anthranilamide inhibitors of factor Xa. , 2007, Bioorganic & medicinal chemistry letters.

[17]  Chong-Hwan Chang,et al.  SAR and X-ray structures of enantiopure 1,2-cis-(1R,2S)-cyclopentyldiamine and cyclohexyldiamine derivatives as inhibitors of coagulation Factor Xa. , 2007, Bioorganic & medicinal chemistry letters.

[18]  N. Haginoya,et al.  Cycloalkanediamine derivatives as novel blood coagulation factor Xa inhibitors. , 2007, Bioorganic & medicinal chemistry letters.

[19]  Bin Ye,et al.  Thiophene-anthranilamides as highly potent and orally available factor Xa inhibitors. , 2007, Journal of medicinal chemistry.

[20]  B. Zhu,et al.  Design, synthesis, and SAR of anthranilamide-based factor Xa inhibitors incorporating substituted biphenyl P4 motifs. , 2004, Bioorganic & medicinal chemistry letters.

[21]  J. Woolfrey,et al.  Design, synthesis, and SAR of anthranilamide-based factor Xa inhibitors with improved functional activity. , 2004, Bioorganic & medicinal chemistry letters.

[22]  Yuo-Ling Chou,et al.  Structure—Activity Relationships of Substituted Benzothiopheneanthranilamide Factor Xa Inhibitors. , 2003 .

[23]  D. Davey,et al.  Structure-activity relationships of substituted benzothiophene-anthranilamide factor Xa inhibitors. , 2003, Bioorganic & medicinal chemistry letters.

[24]  Bin Ye,et al.  Crystal structures of two potent nonamidine inhibitors bound to factor Xa. , 2002, Biochemistry.

[25]  J. A. Kyle,et al.  N(2)-Aroylanthranilamide inhibitors of human factor Xa. , 2000, Journal of medicinal chemistry.

[26]  W. Jenks,et al.  The Photochemistry of Sulfoxides and Related Compounds , 1998 .

[27]  Y. Terada,et al.  Antithrombotic and Hemorrhagic Effects of DX-9065a, a Direct and Selective Factor Xa Inhibitor: Comparison with a Direct Thrombin Inhibitor and Antithrombin Ill-Dependent Anticoagulants , 1997, Thrombosis and Haemostasis.

[28]  H. Ishihara,et al.  DX-9065a, an Orally Active, Specific Inhibitor of Factor Xa, Inhibits Thrombosis without Affecting Bleeding Time in Rats , 1995, Thrombosis and Haemostasis.

[29]  Carl R. Johnson,et al.  Chemistry of sulfoxides and related compounds. XXVI. Preparation and synthetic applications of (dimethylamino)phenyloxosulfonium methylide , 1970 .