Orally bioavailable pyridine and pyrimidine-based Factor XIa inhibitors: Discovery of the methyl N-phenyl carbamate P2 prime group
- Authors:
- Publication Date:
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1358846
- Grant/Contract Number:
- AC02-06CH11357
- Resource Type:
- Publisher's Accepted Manuscript
- Journal Name:
- Bioorganic and Medicinal Chemistry
- Additional Journal Information:
- Journal Name: Bioorganic and Medicinal Chemistry Journal Volume: 24 Journal Issue: 10; Journal ID: ISSN 0968-0896
- Publisher:
- Elsevier
- Country of Publication:
- United Kingdom
- Language:
- English
Citation Formats
Corte, James R., Fang, Tianan, Pinto, Donald J. P., Orwat, Michael J., Rendina, Alan R., Luettgen, Joseph M., Rossi, Karen A., Wei, Anzhi, Ramamurthy, Vidhyashankar, Myers, Jr., Joseph E., Sheriff, Steven, Narayanan, Rangaraj, Harper, Timothy W., Zheng, Joanna J., Li, Yi-Xin, Seiffert, Dietmar A., Wexler, Ruth R., and Quan, Mimi L. Orally bioavailable pyridine and pyrimidine-based Factor XIa inhibitors: Discovery of the methyl N-phenyl carbamate P2 prime group. United Kingdom: N. p., 2016.
Web. doi:10.1016/j.bmc.2016.03.062.
Corte, James R., Fang, Tianan, Pinto, Donald J. P., Orwat, Michael J., Rendina, Alan R., Luettgen, Joseph M., Rossi, Karen A., Wei, Anzhi, Ramamurthy, Vidhyashankar, Myers, Jr., Joseph E., Sheriff, Steven, Narayanan, Rangaraj, Harper, Timothy W., Zheng, Joanna J., Li, Yi-Xin, Seiffert, Dietmar A., Wexler, Ruth R., & Quan, Mimi L. Orally bioavailable pyridine and pyrimidine-based Factor XIa inhibitors: Discovery of the methyl N-phenyl carbamate P2 prime group. United Kingdom. https://doi.org/10.1016/j.bmc.2016.03.062
Corte, James R., Fang, Tianan, Pinto, Donald J. P., Orwat, Michael J., Rendina, Alan R., Luettgen, Joseph M., Rossi, Karen A., Wei, Anzhi, Ramamurthy, Vidhyashankar, Myers, Jr., Joseph E., Sheriff, Steven, Narayanan, Rangaraj, Harper, Timothy W., Zheng, Joanna J., Li, Yi-Xin, Seiffert, Dietmar A., Wexler, Ruth R., and Quan, Mimi L. Sun .
"Orally bioavailable pyridine and pyrimidine-based Factor XIa inhibitors: Discovery of the methyl N-phenyl carbamate P2 prime group". United Kingdom. https://doi.org/10.1016/j.bmc.2016.03.062.
@article{osti_1358846,
title = {Orally bioavailable pyridine and pyrimidine-based Factor XIa inhibitors: Discovery of the methyl N-phenyl carbamate P2 prime group},
author = {Corte, James R. and Fang, Tianan and Pinto, Donald J. P. and Orwat, Michael J. and Rendina, Alan R. and Luettgen, Joseph M. and Rossi, Karen A. and Wei, Anzhi and Ramamurthy, Vidhyashankar and Myers, Jr., Joseph E. and Sheriff, Steven and Narayanan, Rangaraj and Harper, Timothy W. and Zheng, Joanna J. and Li, Yi-Xin and Seiffert, Dietmar A. and Wexler, Ruth R. and Quan, Mimi L.},
abstractNote = {},
doi = {10.1016/j.bmc.2016.03.062},
journal = {Bioorganic and Medicinal Chemistry},
number = 10,
volume = 24,
place = {United Kingdom},
year = {Sun May 01 00:00:00 EDT 2016},
month = {Sun May 01 00:00:00 EDT 2016}
}
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https://doi.org/10.1016/j.bmc.2016.03.062
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Works referenced in this record:
Phenylimidazoles as Potent and Selective Inhibitors of Coagulation Factor XIa with in Vivo Antithrombotic Activity
journal, November 2014
- Hangeland, Jon J.; Friends, Todd J.; Rossi, Karen A.
- Journal of Medicinal Chemistry, Vol. 57, Issue 23
A facile synthesis of statine and analogs by reduction of .beta.-keto esters derived from Boc-protected amino acids. HPLC analyses of their enantiomeric purity
journal, February 1988
- Maibaum, Juergen; Rich, Daniel H.
- The Journal of Organic Chemistry, Vol. 53, Issue 4
Reduced incidence of ischemic stroke in patients with severe factor XI deficiency
journal, April 2008
- Salomon, Ophira; Steinberg, David M.; Koren-Morag, Nira
- Blood, Vol. 111, Issue 8
Factor XI contributes to thrombus propagation on injured neointima of the rabbit iliac artery
journal, July 2006
- Yamashita, A.; Nishihira, K.; Kitazawa, T.
- Journal of Thrombosis and Haemostasis, Vol. 4, Issue 7
Synthesis of (2R)-1-(4-Chloro-2-pyridyl)-2-(2-pyridyl)ethylamine: A Selective Oxime Reduction and Crystallization-Induced Asymmetric Transformation
journal, August 1996
- Negi, Shigeto; Matsukura, Masayuki; Mizuno, Masanori
- Synthesis, Vol. 1996, Issue 08
Preparation of primary amines and 2-azetidinones via N-(trimethylsilyl)imines
journal, February 1983
- Hart, David J.; Kanai, Kenichi; Thomas, Dudley G.
- The Journal of Organic Chemistry, Vol. 48, Issue 3
On the fast translation functions for molecular replacement
journal, July 1995
- Navaza, J.; Vernoslova, E.
- Acta Crystallographica Section A Foundations of Crystallography, Vol. 51, Issue 4
Design, Synthesis, and Biological Evaluation of Peptidomimetic Inhibitors of Factor XIa as Novel Anticoagulants
journal, December 2006
- Lin, Jian; Deng, Hongfeng; Jin, Lei
- Journal of Medicinal Chemistry, Vol. 49, Issue 26
Refinement of severely incomplete structures with maximum likelihood in BUSTER–TNT
journal, November 2004
- Blanc, E.; Roversi, P.; Vonrhein, C.
- Acta Crystallographica Section D Biological Crystallography, Vol. 60, Issue 12
Reversal of diastereoselection in the addition of Grignard reagents to chiral 2-pyridyl tert-butyl (Ellman) sulfinimines
journal, August 2004
- Kuduk, Scott D.; DiPardo, Robert M.; Chang, Ronald K.
- Tetrahedron Letters, Vol. 45, Issue 35
FXI Is Essential for Thrombus Formation Following FeCl3-Induced Injury of the Carotid Artery in the Mouse
journal, January 2002
- Rosen, Elliot; Gailani, Dave; Castellino, Francis
- Thrombosis and Haemostasis, Vol. 87, Issue 04
How good are my data and what is the resolution?
journal, June 2013
- Evans, Philip R.; Murshudov, Garib N.
- Acta Crystallographica Section D Biological Crystallography, Vol. 69, Issue 7
Inhibition of the intrinsic coagulation pathway factor XI by antisense oligonucleotides: a novel antithrombotic strategy with lowered bleeding risk
journal, November 2010
- Zhang, Hong; Löwenberg, Ester C.; Crosby, Jeffrey R.
- Blood, Vol. 116, Issue 22
Clavatadine A, A Natural Product with Selective Recognition and Irreversible Inhibition of Factor XIa †
journal, June 2008
- Buchanan, Malcolm S.; Carroll, Anthony R.; Wessling, Deborah
- Journal of Medicinal Chemistry, Vol. 51, Issue 12
Patients with severe factor XI deficiency have a reduced incidence of deep-vein thrombosis
journal, January 2011
- Salomon, Ophira; Steinberg, David; Zucker, Michal
- Thrombosis and Haemostasis, Vol. 105, Issue 02
Synthesis, Properties, and Reactions of 1 H -Indazol-3-ols and 1,2-Dihydro-3 H -indazol-3-ones
journal, January 1978
- Baiocchi, Leandro; Corsi, Giorgio; Palazzo, Giuseppe
- Synthesis, Vol. 1978, Issue 09
Discovery and Evaluation of Potent P 1 Aryl Heterocycle-Based Thrombin Inhibitors
journal, June 2004
- Young, Mary Beth; Barrow, James C.; Glass, Kristen L.
- Journal of Medicinal Chemistry, Vol. 47, Issue 12
The CCP4 suite programs for protein crystallography
journal, September 1994
- ,
- Acta Crystallographica Section D Biological Crystallography, Vol. 50, Issue 5, p. 760-763
Novel one-pot cyclization of ortho substituted benzonitriles to 3-amino-1,2-benzisoxazoles
journal, April 1996
- Palermo, M. G.
- Tetrahedron Letters, Vol. 37, Issue 17
Stereoselective synthesis of a novel pseudopeptide hapten for the generation of hydrolytic catalytic antibodies
journal, June 2004
- Rodriguez, Ana Chiva; Ramos, Anna Picó; Hawkes, Geoffrey E.
- Tetrahedron: Asymmetry, Vol. 15, Issue 12
Integration, scaling, space-group assignment and post-refinement
journal, January 2010
- Kabsch, Wolfgang
- Acta Crystallographica Section D Biological Crystallography, Vol. 66, Issue 2, p. 133-144
XDS
journal, January 2010
- Kabsch, Wolfgang
- Acta Crystallographica Section D Biological Crystallography, Vol. 66, Issue 2
Antithrombotic Effect of Antisense Factor XI Oligonucleotide Treatment in Primates
journal, July 2013
- Crosby, Jeffrey R.; Marzec, Ulla; Revenko, Alexey S.
- Arteriosclerosis, Thrombosis, and Vascular Biology, Vol. 33, Issue 7
Large scale synthesis of 4-ethylpyrimidine
journal, August 1992
- Butters, M.
- Journal of Heterocyclic Chemistry, Vol. 29, Issue 5
Antithrombotic and hemostatic effects of a small molecule factor XIa inhibitor in rats
journal, September 2007
- Schumacher, William A.; Seiler, Steven E.; Steinbacher, Thomas E.
- European Journal of Pharmacology, Vol. 570, Issue 1-3
Factor XI as a target for antithrombotic therapy
journal, September 2014
- Bane, Charles E.; Gailani, David
- Drug Discovery Today, Vol. 19, Issue 9
Bacterial translation inhibitors, 1-acylindazol-3-ols as anthranilic acid mimics
journal, December 2008
- Stiff, Cory; Graber, David R.; Thorarensen, Atli
- Bioorganic & Medicinal Chemistry Letters, Vol. 18, Issue 23
High Levels of Coagulation Factor XI as a Risk Factor for Venous Thrombosis
journal, March 2000
- Meijers, Joost C. M.; Tekelenburg, Winnie L. H.; Bouma, Bonno N.
- New England Journal of Medicine, Vol. 342, Issue 10
Design and synthesis of macrocyclic indoles targeting blood coagulation cascade Factor XIa
journal, December 2010
- Hanessian, Stephen; Larsson, Andreas; Fex, Tomas
- Bioorganic & Medicinal Chemistry Letters, Vol. 20, Issue 23
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
- Pinto, Donald J. P.; Orwat, Michael J.; Koch, Stephanie
- Journal of Medicinal Chemistry, Vol. 50, Issue 22
Synthesis and in vitro biological evaluation of aryl boronic acids as potential inhibitors of factor XIa
journal, October 2006
- Lazarova, Tsvetelina I.; Jin, Lei; Rynkiewicz, Michael
- Bioorganic & Medicinal Chemistry Letters, Vol. 16, Issue 19
Prevention of vascular graft occlusion and thrombus-associated thrombin generation by inhibition of factor XI
journal, January 2009
- Tucker, Erik I.; Marzec, Ulla M.; White, Tara C.
- Blood, Vol. 113, Issue 4
Application of Fragment Screening and Fragment Linking to the Discovery of Novel Thrombin Inhibitors
journal, January 2006
- Howard, Nigel; Abell, Chris; Blakemore, Wendy
- Journal of Medicinal Chemistry, Vol. 49, Issue 4
Allosteric Modification of Factor XIa Functional Activity upon Binding to Polyanions †
journal, June 2004
- Sinha, Dipali; Badellino, Karen O.; Marcinkiewicz, Mariola
- Biochemistry, Vol. 43, Issue 23
Features and development of Coot
journal, March 2010
- Emsley, P.; Lohkamp, B.; Scott, W. G.
- Acta Crystallographica Section D Biological Crystallography, Vol. 66, Issue 4
AMoRe : an automated package for molecular replacement
journal, March 1994
- Navaza, J.
- Acta Crystallographica Section A Foundations of Crystallography, Vol. 50, Issue 2
Silyl-Mediated Halogen/Halogen Displacement in Pyridines and Other Heterocycles
journal, December 2002
- Schlosser, Manfred; Cottet, Fabrice
- European Journal of Organic Chemistry, Vol. 2002, Issue 24
Synthesis, SAR exploration, and X-ray crystal structures of factor XIa inhibitors containing an α-ketothiazole arginine
journal, June 2006
- Deng, Hongfeng; Bannister, Thomas D.; Jin, Lei
- Bioorganic & Medicinal Chemistry Letters, Vol. 16, Issue 11
Structure-based design of inhibitors of coagulation factor XIa with novel P1 moieties
journal, April 2015
- Pinto, Donald J. P.; Smallheer, Joanne M.; Corte, James R.
- Bioorganic & Medicinal Chemistry Letters, Vol. 25, Issue 7
Tetrahydroquinoline Derivatives as Potent and Selective Factor XIa Inhibitors
journal, January 2014
- Quan, Mimi L.; Wong, Pancras C.; Wang, Cailan
- Journal of Medicinal Chemistry, Vol. 57, Issue 3
Effects of factor IX or factor XI deficiency on ferric chloride-induced carotid artery occlusion in mice: Thrombosis in FIX- and FXI-deficient mice
journal, February 2005
- Wang, X.; Cheng, Q.; Xu, L.
- Journal of Thrombosis and Haemostasis, Vol. 3, Issue 4
Factor XI–dependence of surface- and tissue factor–initiated thrombus propagation in primates
journal, August 2003
- Gruber, András; Hanson, Stephen R.
- Blood, Vol. 102, Issue 3
Inherited factor XI deficiency confers no protection against acute myocardial infarction
journal, April 2003
- Salomon, O.; Steinberg, D. M.; Dardik, R.
- Journal of Thrombosis and Haemostasis, Vol. 1, Issue 4
Factor XI Antisense Oligonucleotide for Prevention of Venous Thrombosis
journal, January 2015
- Büller, Harry R.; Bethune, Claudette; Bhanot, Sanjay
- New England Journal of Medicine, Vol. 372, Issue 3
In vitro, antithrombotic and bleeding time studies of BMS-654457, a small-molecule, reversible and direct inhibitor of factor XIa
journal, August 2015
- Wong, Pancras C.; Quan, Mimi L.; Watson, Carol A.
- Journal of Thrombosis and Thrombolysis, Vol. 40, Issue 4
Effects of factor XI deficiency on ferric chloride-induced vena cava thrombosis in mice
journal, September 2006
- Wang, X.; Smith, P. L.; Hsu, M-Y.
- Journal of Thrombosis and Haemostasis, Vol. 4, Issue 9
Levels of intrinsic coagulation factors and the risk of myocardial infarction among men: opposite and synergistic effects of factors XI and XII
journal, December 2006
- Doggen, Carine J. M.; Rosendaal, Frits R.; Meijers, Joost C. M.
- Blood, Vol. 108, Issue 13
Designing Allosteric Inhibitors of Factor XIa. Lessons from the Interactions of Sulfated Pentagalloylglucopyranosides
journal, December 2013
- Al-Horani, Rami A.; Desai, Umesh R.
- Journal of Medicinal Chemistry, Vol. 57, Issue 11
Pyridine and pyridinone-based factor XIa inhibitors
journal, February 2015
- Corte, James R.; Fang, Tianan; Hangeland, Jon J.
- Bioorganic & Medicinal Chemistry Letters, Vol. 25, Issue 4
A small-molecule factor XIa inhibitor produces antithrombotic efficacy with minimal bleeding time prolongation in rabbits
journal, May 2011
- Wong, Pancras C.; Crain, Earl J.; Watson, Carol A.
- Journal of Thrombosis and Thrombolysis, Vol. 32, Issue 2