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5P9J
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BTK1 COCRYSTALLIZED WITH IBRUTINIB
Descriptor:Tyrosine-protein kinase BTK, 1-[(3~{R})-3-[4-azanyl-3-(4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]propan-1-one
Authors:Gardberg, A.S.
Deposit date:2016-09-20
Release date:2017-05-24
Last modified:2018-02-21
Method:X-RAY DIFFRACTION (1.08 Å)
Cite:Ability of Bruton's Tyrosine Kinase Inhibitors to Sequester Y551 and Prevent Phosphorylation Determines Potency for Inhibition of Fc Receptor but not B-Cell Receptor Signaling.
Mol. Pharmacol., 91, 2017
6DI1
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CRYSTAL STRUCTURE OF BTK IN COMPLEX WITH COVALENT FRAGMENT LIGAND
Descriptor:Tyrosine-protein kinase BTK, 4-amino-2-[(3S)-3-(propanoylamino)pyrrolidin-1-yl]pyrimidine-5-carboxamide
Authors:Jiang, X.
Deposit date:2018-05-22
Release date:2018-10-17
Last modified:2018-10-24
Method:X-RAY DIFFRACTION (1.1 Å)
Cite:Discovery of a novel series of pyridine and pyrimidine carboxamides as potent and selective covalent inhibitors of Btk.
Bioorg. Med. Chem. Lett., 28, 2018
5P9I
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BTK1 SOAKED WITH IBRUTINIB-REV
Descriptor:Tyrosine-protein kinase BTK, 1-{(3R)-3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl}prop-2-en-1-one, DIMETHYL SULFOXIDE
Authors:Gardberg, A.S.
Deposit date:2016-09-20
Release date:2017-05-24
Last modified:2018-02-21
Method:X-RAY DIFFRACTION (1.11 Å)
Cite:Ability of Bruton's Tyrosine Kinase Inhibitors to Sequester Y551 and Prevent Phosphorylation Determines Potency for Inhibition of Fc Receptor but not B-Cell Receptor Signaling.
Mol. Pharmacol., 91, 2017
6HRP
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CRYSTAL STRUCTURE OF BTK KINASE DOMAIN COMPLEXED WITH 6-(DIMETHYLAMINO)-2-[2-(HYDROXYMETHYL)-3-[1-METHYL-5-[[5-(MORPHOLINE-4-CARBONYL)-2-PYRIDYL]AMINO]-6-OXO-3-PYRIDYL]PHENYL]-3,4-DIHYDROISOQUINOLIN-1-ONE
Descriptor:Tyrosine-protein kinase BTK, 6-~{tert}-butyl-8-fluoranyl-2-[2-(hydroxymethyl)-3-[1-methyl-5-[(5-morpholin-4-ylcarbonylpyridin-2-yl)amino]-6-oxidanylidene-pyridazin-3-yl]phenyl]phthalazin-1-one
Authors:Janson, C., Kuglstatter, A.
Deposit date:2018-09-28
Release date:2019-03-20
Method:X-RAY DIFFRACTION (1.12 Å)
Cite:A potent seven-membered cyclic BTK (Bruton's tyrosine Kinase) chiral inhibitor conceived by structure-based drug design to lock its bioactive conformation.
Bioorg.Med.Chem.Lett., 2019
6E4F
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CRYSTAL STRUCTURE OF ARQ 531 IN COMPLEX WITH THE KINASE DOMAIN OF BTK
Descriptor:Tyrosine-protein kinase BTK, 1,5-anhydro-2-{[5-(2-chloro-4-phenoxybenzene-1-carbonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amino}-2,3,4-trideoxy-D-erythro-hexitol, IMIDAZOLE, ...
Authors:Eathiraj, S.
Deposit date:2018-07-17
Release date:2018-09-05
Last modified:2018-10-10
Method:X-RAY DIFFRACTION (1.15 Å)
Cite:The BTK Inhibitor ARQ 531 Targets Ibrutinib-Resistant CLL and Richter Transformation.
Cancer Discov, 8, 2018
4RFZ
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CRYSTAL STRUCTURE OF BTK KINASE DOMAIN COMPLEXED WITH 6-(DIMETHYLAMINO)-8-FLUORO-2-[2-(HYDROXYMETHYL)-3-[1-METHYL-5-[[5-(MORPHOLINE-4-CARBONYL)-2-PYRIDYL]AMINO]-6-OXO-3-PYRIDYL]PHENYL]ISOQUINOLIN-1-ONE
Descriptor:Tyrosine-protein kinase BTK, 6-(dimethylamino)-8-fluoro-2-[2-(hydroxymethyl)-3-(1-methyl-5-{[5-(morpholin-4-ylcarbonyl)pyridin-2-yl]amino}-6-oxo-1,6-dihydropyridin-3-yl)phenyl]isoquinolin-1(2H)-one, DIMETHYL SULFOXIDE
Authors:Kuglstatter, A., Wong, A.
Deposit date:2014-09-29
Release date:2014-12-24
Last modified:2015-01-14
Method:X-RAY DIFFRACTION (1.17 Å)
Cite:Finding the perfect spot for fluorine: Improving potency up to 40-fold during a rational fluorine scan of a Bruton's Tyrosine Kinase (BTK) inhibitor scaffold.
Bioorg.Med.Chem.Lett., 25, 2015
5P9L
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BTK1 IN COMPLEX WITH CC 292
Descriptor:Tyrosine-protein kinase BTK, ~{N}-[3-[[5-fluoranyl-2-[[4-(2-methoxyethoxy)phenyl]amino]pyrimidin-4-yl]amino]phenyl]propanamide
Authors:Gardberg, A.S.
Deposit date:2016-09-20
Release date:2017-05-24
Last modified:2018-02-21
Method:X-RAY DIFFRACTION (1.25 Å)
Cite:Ability of Bruton's Tyrosine Kinase Inhibitors to Sequester Y551 and Prevent Phosphorylation Determines Potency for Inhibition of Fc Receptor but not B-Cell Receptor Signaling.
Mol. Pharmacol., 91, 2017
6DI9
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CRYSTAL STRUCTURE OF BTK IN COMPLEX WITH COVALENT INHIBITOR
Descriptor:Tyrosine-protein kinase BTK, 6-[(3S)-3-(acryloylamino)pyrrolidin-1-yl]-2-{[4-(tert-butylcarbamoyl)phenyl]amino}pyridine-3-carboxamide, DIMETHYL SULFOXIDE
Authors:GARDBERG, A.
Deposit date:2018-05-23
Release date:2018-09-05
Method:X-RAY DIFFRACTION (1.25 Å)
Cite:Discovery of potent, highly selective covalent irreversible BTK inhibitors from a fragment hit.
Bioorg. Med. Chem. Lett., 28, 2018
5P9K
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CRYSTAL STRUCTURE OF BTK WITH CNX 774
Descriptor:Tyrosine-protein kinase BTK, 4-[4-[[5-fluoranyl-4-[[3-(propanoylamino)phenyl]amino]pyrimidin-2-yl]amino]phenoxy]-~{N}-methyl-pyridine-2-carboxamide
Authors:Gardberg, A.S.
Deposit date:2016-09-20
Release date:2017-05-24
Last modified:2018-02-21
Method:X-RAY DIFFRACTION (1.28 Å)
Cite:Ability of Bruton's Tyrosine Kinase Inhibitors to Sequester Y551 and Prevent Phosphorylation Determines Potency for Inhibition of Fc Receptor but not B-Cell Receptor Signaling.
Mol. Pharmacol., 91, 2017
6BLN
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BTK COMPLEX WITH COMPOUND 13
Descriptor:Tyrosine-protein kinase BTK, SULFATE ION, N-(3-{5-[(1,5-dimethyl-1H-pyrazol-3-yl)amino]-6-oxo-1,6-dihydropyridazin-3-yl}-2,6-difluorophenyl)-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide, ...
Authors:Kiefer, J.R., Eigenbrot, C., Yu, C.L.
Deposit date:2017-11-10
Release date:2018-11-07
Last modified:2019-02-27
Method:X-RAY DIFFRACTION (1.3 Å)
Cite:Water molecules in protein-ligand interfaces. Evaluation of software tools and SAR comparison.
J. Comput. Aided Mol. Des., 2019
6DI0
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CRYSTAL STRUCTURE OF BTK IN COMPLEX WITH FRAGMENT LIGAND
Descriptor:Tyrosine-protein kinase BTK, 6-(cyclohexylamino)pyridine-3-carboxamide
Authors:MOCHALKIN, I.
Deposit date:2018-05-22
Release date:2018-10-17
Last modified:2018-10-24
Method:X-RAY DIFFRACTION (1.3 Å)
Cite:Discovery of a novel series of pyridine and pyrimidine carboxamides as potent and selective covalent inhibitors of Btk.
Bioorg. Med. Chem. Lett., 28, 2018
5U9D
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DISCOVERY OF A POTENT BTK INHIBITOR WITH A NOVEL BINDING MODE USING PARALLEL SELECTIONS WITH A DNA-ENCODED CHEMICAL LIBRARY
Descriptor:Tyrosine-protein kinase BTK, (R)-N-methyl-2-(3-((quinoxalin-6-ylamino)methyl)furan-2-carbonyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxamide, 1,2-ETHANEDIOL, ...
Authors:Cuozzo, J.W., Centrella, P.A., Gikunju, D., Habeshian, S., Hupp, C.D., Keefe, A.D., Sigel, E., Soutter, H.H., Thomson, H.A., Zhang, Y., Clark, M.A.
Deposit date:2016-12-16
Release date:2017-01-18
Last modified:2017-05-10
Method:X-RAY DIFFRACTION (1.33 Å)
Cite:Discovery of a Potent BTK Inhibitor with a Novel Binding Mode by Using Parallel Selections with a DNA-Encoded Chemical Library.
Chembiochem, 18, 2017
4RX5
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BRUTON'S TYROSINE KINASE (BTK) WITH PYRIDAZINONE COMPOUND 23
Descriptor:Tyrosine-protein kinase BTK, SULFATE ION, GLYCEROL, ...
Authors:Eigenbrot, C., Yu, C.
Deposit date:2014-12-08
Release date:2015-12-02
Last modified:2016-03-23
Method:X-RAY DIFFRACTION (1.356 Å)
Cite:Discovery of highly potent and selective Bruton's tyrosine kinase inhibitors: Pyridazinone analogs with improved metabolic stability.
Bioorg.Med.Chem.Lett., 26, 2016
6HRT
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CRYSTAL STRUCTURE OF BTK KINASE DOMAIN COMPLEXED WITH 12-(6-TERT-BUTYL-8-FLUORO-1-OXO-PHTHALAZIN-2-YL)-9-HYDROXY-6-METHYL-4-[[5-(MORPHOLINE-4-CARBONYL)-2-PYRIDYL]AMINO]-6-AZATRICYCLO[9.4.0.02,7]PENTADECA-1(15),2(7),3,11,13-PENTAEN-5-ONE
Descriptor:Tyrosine-protein kinase BTK, (9~{S})-12-(6-~{tert}-butyl-8-fluoranyl-1-oxidanylidene-phthalazin-2-yl)-6-methyl-4-[(5-morpholin-4-ylcarbonylpyridin-2-yl)amino]-9-oxidanyl-6-azatricyclo[9.4.0.0^{2,7}]pentadeca-1(15),2(7),3,11,13-pentaen-5-one
Authors:Kuglstatter, A., Janson, C.
Deposit date:2018-09-28
Release date:2019-03-20
Method:X-RAY DIFFRACTION (1.36 Å)
Cite:A potent seven-membered cyclic BTK (Bruton's tyrosine Kinase) chiral inhibitor conceived by structure-based drug design to lock its bioactive conformation.
Bioorg.Med.Chem.Lett., 2019
5KUP
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BRUTON'S TYROSINE KINASE (BTK) WITH PYRIDAZINONE COMPOUND 9
Descriptor:Tyrosine-protein kinase BTK, SULFATE ION, GLYCEROL, ...
Authors:Eigenbrot, C., Yu, C.
Deposit date:2016-07-13
Release date:2016-09-14
Last modified:2016-11-02
Method:X-RAY DIFFRACTION (1.389 Å)
Cite:Battling Btk Mutants With Noncovalent Inhibitors That Overcome Cys481 and Thr474 Mutations.
Acs Chem.Biol., 11, 2016
6NFH
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BTK IN COMPLEX WITH INHIBITOR 8-(2,3-DIHYDRO-1H-INDEN-5-YL)-2-({4-[(2S)-3-(DIMETHYLAMINO)-2-HYDROXYPROPOXY]PHENYL}AMINO)-5,8-DIHYDROPTERIDINE-6,7-DIONE
Descriptor:Tyrosine-protein kinase BTK, 8-(2,3-dihydro-1H-inden-5-yl)-2-({4-[(2S)-3-(dimethylamino)-2-hydroxypropoxy]phenyl}amino)-5,8-dihydropteridine-6,7-dione, 1,2-ETHANEDIOL
Authors:Mirzadegan, T., Damm-Ganamet, K.L.
Deposit date:2018-12-20
Release date:2019-03-13
Method:X-RAY DIFFRACTION (1.4 Å)
Cite:Accelerating Lead Identification by High Throughput Virtual Screening: Prospective Case Studies from the Pharmaceutical Industry.
J Chem Inf Model, 2019
5P9M
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BTK1 BINDS COVALENTLY TO HY-15771 ONO-4059
Descriptor:Tyrosine-protein kinase BTK, 6-azanyl-9-[(3~{R})-1-[(~{E})-but-2-enoyl]pyrrolidin-3-yl]-7-(4-phenoxyphenyl)purin-8-one, DIMETHYL SULFOXIDE
Authors:Gardberg, A.S.
Deposit date:2016-09-20
Release date:2017-05-24
Last modified:2018-02-21
Method:X-RAY DIFFRACTION (1.41 Å)
Cite:Ability of Bruton's Tyrosine Kinase Inhibitors to Sequester Y551 and Prevent Phosphorylation Determines Potency for Inhibition of Fc Receptor but not B-Cell Receptor Signaling.
Mol. Pharmacol., 91, 2017
6DI5
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CRYSTAL STRUCTURE OF BTK IN COMPLEX WITH COVALENT INHIBITOR
Descriptor:Tyrosine-protein kinase BTK, 2-(4-phenoxyphenoxy)-6-[(1S,4S)-5-propanoyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]pyridine-3-carboxamide, DIMETHYL SULFOXIDE
Authors:Gardberg, A.
Deposit date:2018-05-22
Release date:2018-09-05
Method:X-RAY DIFFRACTION (1.42 Å)
Cite:Discovery of potent, highly selective covalent irreversible BTK inhibitors from a fragment hit.
Bioorg. Med. Chem. Lett., 28, 2018
6BKW
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BTK COMPLEX WITH COMPOUND 12
Descriptor:Tyrosine-protein kinase BTK, SULFATE ION, N-(3-{5-[(1,5-dimethyl-1H-pyrazol-3-yl)amino]-1-methyl-6-oxo-1,6-dihydropyridazin-3-yl}-2,6-difluorophenyl)-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide, ...
Authors:Kiefer, J.R., Eigenbrot, C., Yu, C.L.
Deposit date:2017-11-09
Release date:2018-11-07
Last modified:2019-02-27
Method:X-RAY DIFFRACTION (1.499 Å)
Cite:Water molecules in protein-ligand interfaces. Evaluation of software tools and SAR comparison.
J. Comput. Aided Mol. Des., 2019
5T18
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CRYSTAL STRUCTURE OF BRUTON AGAMMABULINEMIA TYROSINE KINASE COMPLEXED WITH BMS-986142 AKA (2S)-6-FLUORO-5-[3-(8-FLUORO-1-METHYL-2,4-DIOXO-1,2,3,4-TETRAHYDROQUINAZOLIN-3-YL)-2-METHYLPHENYL]-2-(2-HYDROXYPROPAN-2-YL)-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-8-CARBOXAMIDE
Descriptor:Tyrosine-protein kinase BTK, 6-Fluoro-5-(R)-(3-(S)-(8-fluoro-1-methyl-2,4-dioxo-1,2-dihydroquinazolin-3(4H)-yl)-2-methylphenyl)-2-(S)-(2-hydroxypropan-2-yl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide
Authors:Muckelbauer, J.K.
Deposit date:2016-08-18
Release date:2017-03-08
Method:X-RAY DIFFRACTION (1.5 Å)
Cite:Discovery of 6-Fluoro-5-(R)-(3-(S)-(8-fluoro-1-methyl-2,4-dioxo-1,2-dihydroquinazolin-3(4H)-yl)-2-methylphenyl)-2-(S)-(2-hydroxypropan-2-yl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (BMS-986142): A Reversible Inhibitor of Bruton's Tyrosine Kinase (BTK) Conformationally Constrained by Two Locked Atropisomers.
J. Med. Chem., 59, 2016
4OT5
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CRYSTAL STRUCTURE OF BTK KINASE DOMAIN COMPLEXED WITH 4-TERT-BUTYL-N-(3-{8-[4-(4-METHYL-PIPERAZINE-1-CARBONYL)-PHENYLAMINO]-IMIDAZO[1,2-A]PYRAZIN-6-YL}-PHENYL)-BENZAMIDE
Descriptor:Tyrosine-protein kinase BTK, 4-tert-butyl-N-{3-[8-({4-[(4-methylpiperazin-1-yl)carbonyl]phenyl}amino)imidazo[1,2-a]pyrazin-6-yl]phenyl}benzamide, DIMETHYL SULFOXIDE
Authors:Kuglstatter, A., Wong, A.
Deposit date:2014-02-13
Release date:2014-05-14
Last modified:2015-01-21
Method:X-RAY DIFFRACTION (1.55 Å)
Cite:Structure-Based Drug Design of RN486, a Potent and Selective Bruton's Tyrosine Kinase (BTK) Inhibitor, for the Treatment of Rheumatoid Arthritis.
J.Med.Chem., 58, 2015
4OTQ
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CRYSTAL STRUCTURE OF BTK KINASE DOMAIN COMPLEXED WITH 1-[5-[3-(7-TERT-BUTYL-4-OXO-QUINAZOLIN-3-YL)-2-METHYL-PHENYL]-1-METHYL-2-OXO-3-PYRIDYL]-3-METHYL-UREA
Descriptor:Tyrosine-protein kinase BTK, 1-{5-[3-(7-tert-butyl-4-oxoquinazolin-3(4H)-yl)-2-methylphenyl]-1-methyl-2-oxo-1,2-dihydropyridin-3-yl}-3-methylurea, DIMETHYL SULFOXIDE
Authors:Kuglstatter, A., Wong, A.
Deposit date:2014-02-14
Release date:2014-05-14
Last modified:2015-01-21
Method:X-RAY DIFFRACTION (1.55 Å)
Cite:Structure-Based Drug Design of RN486, a Potent and Selective Bruton's Tyrosine Kinase (BTK) Inhibitor, for the Treatment of Rheumatoid Arthritis.
J.Med.Chem., 58, 2015
5BQ0
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CRYSTAL STRUCTURE OF BRUTON AGAMMAGLOBULINEMIA TYROSINE KINASE COMPLEXED WITH BMS-824171 AKA 6-[(3R)-3-(4-TERT-BU TYLBENZAMIDO)PIPERIDIN-1-YL]-2-{[4-(MORPHOLINE-4-CARBONYL) PHENYL]AMINO}PYRIDINE-3-CARBOXAMIDE
Descriptor:Tyrosine-protein kinase BTK, 4-(2-chlorophenyl)-7-[(4-methylpiperazin-1-yl)carbonyl]-9H-carbazole-1-carboxamide, DIMETHYL SULFOXIDE, ...
Authors:Muckelbauer, J.K.
Deposit date:2015-05-28
Release date:2015-09-23
Method:X-RAY DIFFRACTION (1.57 Å)
Cite:Design and synthesis of carbazole carboxamides as promising inhibitors of Bruton's tyrosine kinase (BTK) and Janus kinase 2 (JAK2).
Bioorg.Med.Chem.Lett., 25, 2015
5J87
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DISCOVERY OF N-(3-(5-((3-ACRYLAMIDO-4-(MORPHOLINE-4-CARBONYL)PHENYL)AMINO)-1-METHYL-6-OXO-1,6-DIHYDROPYRIDIN-3-YL)-2-METHYLPHENYL)-4-(TERT-BUTYL)BENZAMIDE (CHMFL-BTK-01) AS A HIGHLY SELECTIVE IRREVERSIBLE BTK KINASE INHIBITOR
Descriptor:Tyrosine-protein kinase BTK, N-[3-(5-{[3-(acryloylamino)-4-(morpholine-4-carbonyl)phenyl]amino}-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-methylphenyl]-4-tert-butylbenzamide
Authors:Yun, C.H., Zhang, S.
Deposit date:2016-04-07
Release date:2017-04-19
Last modified:2017-10-04
Method:X-RAY DIFFRACTION (1.59 Å)
Cite:Discovery of N-(3-(5-((3-acrylamido-4-(morpholine-4-carbonyl)phenyl)amino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-methylphenyl)-4-(tert-butyl)benzamide (CHMFL-BTK-01) as a highly selective irreversible Bruton's tyrosine kinase (BTK) inhibitor.
Eur J Med Chem, 131, 2017
5VFI
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BRUTON'S TYROSINE KINASE (BTK) WITH GDC-0853
Descriptor:Tyrosine-protein kinase BTK, 2-[3'-(hydroxymethyl)-1-methyl-5-({5-[(2S)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl}amino)-6-oxo[1,6-dihydro[3,4'-bipyridine]]-2'-yl]-7,7-dimethyl-3,4,7,8-tetrahydro-2H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-1(6H)-one, 1,2-ETHANEDIOL, ...
Authors:Steinbacher, S., Eigenbrot, C.
Deposit date:2017-04-07
Release date:2018-02-28
Last modified:2018-04-04
Method:X-RAY DIFFRACTION (1.59 Å)
Cite:Discovery of GDC-0853: A Potent, Selective, and Noncovalent Bruton's Tyrosine Kinase Inhibitor in Early Clinical Development.
J. Med. Chem., 61, 2018
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