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Title: Discovery of Potent and Orally Bioavailable Pyridine N-Oxide-Based Factor XIa Inhibitors through Exp

Journal Article · · J. Med. Chem.

Research Organization:
Argonne National Lab. (ANL), Argonne, IL (United States). Advanced Photon Source (APS)
Sponsoring Organization:
DOE - Office Of Science; INDUSTRY
OSTI ID:
1900810
Journal Information:
J. Med. Chem., Vol. 65, Issue (15)
Country of Publication:
United States
Language:
ENGLISH

References (59)

Global Burden of Thrombosis journal April 2016
Thrombosis journal November 2014
Oral Anticoagulant Therapy journal February 2012
Structure-Based Design of Novel Potent Nonpeptide Thrombin Inhibitors journal April 2002
Discovery of 1-(4-Methoxyphenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7-tetrahydro- 1 H -pyrazolo[3,4- c ]pyridine-3-carboxamide (Apixaban, BMS-562247), a Highly Potent, Selective, Efficacious, and Orally Bioavailable Inhibitor of Blood Coagulation Factor Xa journal November 2007
Discovery of the Novel Antithrombotic Agent 5-Chloro- N -({(5 S )-2-oxo-3- [4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene- 2-carboxamide (BAY 59-7939):  An Oral, Direct Factor Xa Inhibitor journal September 2005
New Oral Anticoagulants in Nonvalvular Atrial Fibrillation journal October 2016
Net Clinical Benefit of Warfarin in Patients With Atrial Fibrillation: A Report From the Swedish Atrial Fibrillation Cohort Study journal May 2012
Overview of the New Oral Anticoagulants: Opportunities and Challenges journal May 2015
Antithrombotic Agents journal February 2019
Suboptimal Use of Oral Anticoagulants in Atrial Fibrillation: Has the Introduction of Direct Oral Anticoagulants Improved Prescribing Practices? journal February 2016
Anticoagulation in chronic kidney disease patients--the practical aspects journal August 2014
Factor XIa Inhibitors as New Anticoagulants journal May 2018
Factor XI and contact activation as targets for antithrombotic therapy journal June 2015
Factor XIa inhibitors: A review of the patent literature journal February 2016
Intrinsic Pathway of Coagulation and Thrombosis journal March 2019
The hemostatic role of factor XI journal May 2016
Patients with severe factor XI deficiency have a reduced incidence of deep-vein thrombosis journal January 2011
Factor XI deficiency is associated with lower risk for cardiovascular and venous thromboembolism events journal March 2017
Elevated Factor XI Activity Levels Are Associated With an Increased Odds Ratio for Cerebrovascular Events journal September 2006
High Levels of Coagulation Factor XI as a Risk Factor for Venous Thrombosis journal March 2000
Factor XI Antisense Oligonucleotide for Prevention of Venous Thrombosis journal January 2015
Coagulation factor XI as a novel target for antithrombotic treatment: FXI, target for antithrombotic treatment journal November 2010
Factor XI(a) inhibitors for thrombosis: an updated patent review (2016-present) journal December 2019
Tetrahydroquinoline Derivatives as Potent and Selective Factor XIa Inhibitors journal January 2014
Phenylimidazoles as Potent and Selective Inhibitors of Coagulation Factor XIa with in Vivo Antithrombotic Activity journal November 2014
Novel phenylalanine derived diamides as Factor XIa inhibitors journal January 2016
Discovery of a Parenteral Small Molecule Coagulation Factor XIa Inhibitor Clinical Candidate (BMS-962212) journal November 2017
Structure-Based Design and Preclinical Characterization of Selective and Orally Bioavailable Factor XIa Inhibitors: Demonstrating the Power of an Integrated S1 Protease Family Approach journal June 2020
Potent, Orally Bioavailable, and Efficacious Macrocyclic Inhibitors of Factor XIa. Discovery of Pyridine-Based Macrocycles Possessing Phenylazole Carboxamide P1 Groups journal December 2019
Discovery of a High Affinity, Orally Bioavailable Macrocyclic FXIa Inhibitor with Antithrombotic Activity in Preclinical Species journal May 2020
Discovery of Milvexian, a High-Affinity, Orally Bioavailable Inhibitor of Factor XIa in Clinical Studies for Antithrombotic Therapy journal September 2021
The Protein Data Bank: a historical perspective journal December 2007
How Significant Are Unusual Protein–Ligand Interactions? Insights from Database Mining journal November 2019
Identification of Noncompetitive Protein–Ligand Interactions for Structural Optimization journal October 2020
A Real-World Perspective on Molecular Design: Miniperspective journal February 2016
Carbon-Oxygen Hydrogen Bonding in Biological Structure and Function journal October 2012
CF 2 H, a Hydrogen Bond Donor journal June 2017
Computer Modeling of Halogen Bonds and Other σ-Hole Interactions journal February 2016
Halogen bonds in biological molecules journal November 2004
A Survey of the Role of Noncovalent Sulfur Interactions in Drug Design journal March 2015
Highly Selective MERTK Inhibitors Achieved by a Single Methyl Group journal October 2018
A conserved water-mediated hydrogen bond network defines bosutinib's kinase selectivity journal December 2013
Methyl Effects on Protein–Ligand Binding journal April 2012
Contribution of Explicit Solvent Effects to the Binding Affinity of Small-Molecule Inhibitors in Blood Coagulation Factor Serine Proteases journal April 2011
Extra Precision Glide:  Docking and Scoring Incorporating a Model of Hydrophobic Enclosure for Protein−Ligand Complexes journal October 2006
pH-Dependent Solubility and Permeability Criteria for Provisional Biopharmaceutics Classification (BCS and BDDCS) in Early Drug Discovery journal April 2012
Metabolism and Bioactivation: It’s Time to Expect the Unexpected journal April 2020
Identification and Mitigation of Reactive Metabolites of 2-Aminoimidazole-Containing Microsomal Prostaglandin E Synthase-1 Inhibitors Terminated Due to Clinical Drug-Induced Liver Injury journal February 2018
Jaguar: A high-performance quantum chemistry software program with strengths in life and materials sciences journal July 2013
The Halogen Bond journal January 2016
Role of the Active-Site Solvent in the Thermodynamics of Factor Xa Ligand Binding journal March 2008
Motifs for molecular recognition exploiting hydrophobic enclosure in protein–ligand binding journal January 2007
Kallikrein directly interacts with and activates Factor IX, resulting in thrombin generation and fibrin formation independent of Factor XI journal January 2021
Aldehyde Oxidase: Reaction Mechanism and Prediction of Site of Metabolism journal August 2017
Rapid detection and characterization of minor reactive metabolites using stable-isotope trapping in combination with tandem mass spectrometry journal January 2005
EPSA: A Novel Supercritical Fluid Chromatography Technique Enabling the Design of Permeable Cyclic Peptides journal August 2014
Oxidation of organonitrogen compounds by the methyltrioxorhenium-hydrogen peroxide system journal February 1996
A simple convenient method for preparation of difluoromethyl ethers using fluorosulfonyldifluoroacetic acid as a difluorocarbene precursor journal September 1989