Identification and optimisation of a pyrimidopyridone series of IRAK4 inhibitors

Cumming, Iain A.; Degorce, Sebastien L.; Aagaard, Anna; Braybrooke, Erin L.; Davies, Nichola L.; Diene, Coura R.; Eatherton, Andrew J.; Felstead, Hannah R.; Groombridge, Sam D.; Lenz, Eva M.; Li, Yunxia; Nai, Youfeng; Pearson, Stuart; Robb, Graeme R.; Scott, James S.; Steward, Oliver R.; Wu, Chengyan; Xue, Yafeng; Zhang, Lanping; Zhang, Yanxiu

doi:10.1016/j.bmc.2022.116729

Identification and optimisation of a pyrimidopyridone series of IRAK4 inhibitors

Journal Article · 01 June 2022 · Bioorgan. Med. Chem.

DOI:https://doi.org/10.1016/j.bmc.2022.116729· OSTI ID:1877217

Cumming, Iain A.; Degorce, Sebastien L.; Aagaard, Anna; Braybrooke, Erin L.; Davies, Nichola L.; Diene, Coura R.; Eatherton, Andrew J.; Felstead, Hannah R.; Groombridge, Sam D.; Lenz, Eva M.; Li, Yunxia; Nai, Youfeng; Pearson, Stuart; Robb, Graeme R.; Scott, James S.; Steward, Oliver R.; Wu, Chengyan; Xue, Yafeng; Zhang, Lanping; Zhang, Yanxiu

Research Organization:: Advanced Photon Source (APS), Argonne National Laboratory (ANL), Argonne, IL (US)

Sponsoring Organization:: DOE - Office Of Science; INDUSTRY

OSTI ID:: 1877217

Journal Information:: Bioorgan. Med. Chem., Journal Name: Bioorgan. Med. Chem. Vol. 63

Country of Publication:: United States

Language:: ENGLISH

References (19)

Discovery of a Series of 5-Azaquinazolines as Orally Efficacious IRAK4 Inhibitors Targeting MyD88 ^L265P Mutant Diffuse Large B Cell Lymphoma Degorce, Sébastien L.; Anjum, Rana; Bloecher, Andrew Journal of Medicinal Chemistry, Vol. 62, Issue 21 https://doi.org/10.1021/acs.jmedchem.9b01346	journal	October 2019
NMR Analysis of Molecular Flexibility in Solution: A New Method for the Study of Complex Distributions of Rapidly Exchanging Conformations. Application to a 13-Residue Peptide with an 8-Residue Loop Cicero, D. O.; Barbato, G.; Bazzo, R. Journal of the American Chemical Society, Vol. 117, Issue 3 https://doi.org/10.1021/ja00108a019	journal	January 1995
Estimation of permeability by passive diffusion through Caco-2 cell monolayers using the drugs' lipophilicity and molecular weight Camenisch, Gian; Alsenz, Jochem; van de Waterbeemd, Han European Journal of Pharmaceutical Sciences, Vol. 6, Issue 4 https://doi.org/10.1016/S0928-0987(97)10019-7	journal	October 1998
Selective interleukin-1 receptor–associated kinase 4 inhibitors for the treatment of autoimmune disorders and lymphoid malignancy Kelly, Priscilla N.; Romero, Donna L.; Yang, Yibin Journal of Experimental Medicine, Vol. 212, Issue 13 https://doi.org/10.1084/jem.20151074	journal	November 2015
An NMR Method for the Quantitative Assessment of Intramolecular Hydrogen Bonding; Application to Physicochemical, Environmental, and Biochemical Properties Abraham, Michael H.; Abraham, Raymond J.; Acree, William E. The Journal of Organic Chemistry, Vol. 79, Issue 22 https://doi.org/10.1021/jo502080p	journal	November 2014
Lowering Lipophilicity by Adding Carbon: AzaSpiroHeptanes, a log D Lowering Twist Degorce, Sébastien L.; Bodnarchuk, Michael S.; Scott, James S. ACS Medicinal Chemistry Letters, Vol. 10, Issue 8 https://doi.org/10.1021/acsmedchemlett.9b00248	journal	July 2019
Computer‐Assisted 3D Structure Elucidation of Natural Products using Residual Dipolar Couplings Troche‐Pesqueira, Eduardo; Anklin, Clemens; Gil, Roberto R. Angewandte Chemie International Edition, Vol. 56, Issue 13 https://doi.org/10.1002/anie.201612454	journal	February 2017
Interleukin-1 receptor-associated kinase 4 (IRAK4) inhibitors: an updated patent review (2016-2018) McElroy, William T. Expert Opinion on Therapeutic Patents, Vol. 29, Issue 4 https://doi.org/10.1080/13543776.2019.1597850	journal	March 2019
Improving metabolic stability and removing aldehyde oxidase liability in a 5-azaquinazoline series of IRAK4 inhibitors Degorce, Sébastien L.; Aagaard, Anna; Anjum, Rana Bioorganic & Medicinal Chemistry, Vol. 28, Issue 23 https://doi.org/10.1016/j.bmc.2020.115815	journal	December 2020
EASY ROESY: Reliable Cross-Peak Integration in Adiabatic Symmetrized ROESY Thiele, Christina M.; Petzold, Katja; Schleucher, Jürgen Chemistry - A European Journal, Vol. 15, Issue 3 https://doi.org/10.1002/chem.200802027	journal	January 2009
Lowering Lipophilicity by Adding Carbon: One-Carbon Bridges of Morpholines and Piperazines Degorce, Sébastien L.; Bodnarchuk, Michael S.; Cumming, Iain A. Journal of Medicinal Chemistry, Vol. 61, Issue 19 https://doi.org/10.1021/acs.jmedchem.8b01148	journal	September 2018
Fluorination of 3-(3-(Piperidin-1-yl)propyl)indoles and 3-(3-(Piperazin-1-yl)propyl)indoles Gives Selective Human 5-HT _1D Receptor Ligands with Improved Pharmacokinetic Profiles van Niel, Monique B.; Collins, Ian; Beer, Margaret S. Journal of Medicinal Chemistry, Vol. 42, Issue 12 https://doi.org/10.1021/jm981133m	journal	June 1999
An improved method for the determination of cross-relaxation rates from NOE data Macur, S.; Farmer, B. T.; Brown, L. R. Journal of Magnetic Resonance (1969), Vol. 70, Issue 3 https://doi.org/10.1016/0022-2364(86)90143-5	journal	December 1986
Discovery and Optimization of Pyrrolopyrimidine Inhibitors of Interleukin-1 Receptor Associated Kinase 4 (IRAK4) for the Treatment of Mutant MYD88 ^L265P Diffuse Large B-Cell Lymphoma Scott, James S.; Degorce, Sébastien L.; Anjum, Rana Journal of Medicinal Chemistry, Vol. 60, Issue 24 https://doi.org/10.1021/acs.jmedchem.7b01290	journal	December 2017
Oncogenically active MYD88 mutations in human lymphoma Ngo, Vu N.; Young, Ryan M.; Schmitz, Roland Nature, Vol. 470, Issue 7332 https://doi.org/10.1038/nature09671	journal	December 2010
Severe impairment of interleukin-1 and Toll-like receptor signalling in mice lacking IRAK-4 Suzuki, Nobutaka; Suzuki, Shinobu; Duncan, Gordon S. Nature, Vol. 416, Issue 6882 https://doi.org/10.1038/nature736	journal	March 2002
Optimization of permeability in a series of pyrrolotriazine inhibitors of IRAK4 Degorce, Sébastien L.; Anjum, Rana; Dillman, Keith S. Bioorganic & Medicinal Chemistry, Vol. 26, Issue 4 https://doi.org/10.1016/j.bmc.2018.01.008	journal	February 2018
Novel drug targets for personalized precision medicine in relapsed/refractory diffuse large B-cell lymphoma: a comprehensive review Camicia, Rosalba; Winkler, Hans C.; Hassa, Paul O. Molecular Cancer, Vol. 14, Issue 1 https://doi.org/10.1186/s12943-015-0474-2	journal	December 2015
Discovery of Clinical Candidate 1-{[(2 S ,3 S ,4 S )-3-Ethyl-4-fluoro-5-oxopyrrolidin-2-yl]methoxy}-7-methoxyisoquinoline-6-carboxamide (PF-06650833), a Potent, Selective Inhibitor of Interleukin-1 Receptor Associated Kinase 4 (IRAK4), by Fragment-Based Drug Design Lee, Katherine L.; Ambler, Catherine M.; Anderson, David R. Journal of Medicinal Chemistry, Vol. 60, Issue 13 https://doi.org/10.1021/acs.jmedchem.7b00231	journal	June 2017

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