7YC9
 
 | | Co-crystal structure of BTK kinase domain with inhibitor | | Descriptor: | (7~{S})-2-(4-bromanyl-3,5-dimethoxy-phenyl)-7-(1-propanoylpiperidin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide, 1,2-ETHANEDIOL, Tyrosine-protein kinase BTK | | Authors: | Zhou, X. | | Deposit date: | 2022-07-01 | | Release date: | 2023-05-17 | | Last modified: | 2023-11-29 | | Method: | X-RAY DIFFRACTION (1.4 Å) | | Cite: | Discovery of BGB-8035, a Highly Selective Covalent Inhibitor of Bruton's Tyrosine Kinase for B-Cell Malignancies and Autoimmune Diseases.
J.Med.Chem., 66, 2023
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6NFH
 | | 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: | 1,2-ETHANEDIOL, 8-(2,3-dihydro-1H-inden-5-yl)-2-({4-[(2S)-3-(dimethylamino)-2-hydroxypropoxy]phenyl}amino)-5,8-dihydropteridine-6,7-dione, Tyrosine-protein kinase BTK | | Authors: | Mirzadegan, T, Damm-Ganamet, K.L. | | Deposit date: | 2018-12-20 | | Release date: | 2019-03-13 | | Last modified: | 2023-10-11 | | 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., 59, 2019
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6VXQ
 | | Bruton's tyrosine kinase in complex with compound 5 | | Descriptor: | DIMETHYL SULFOXIDE, N-{[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)phenyl]methyl}benzamide, Tyrosine-protein kinase BTK | | Authors: | Metrick, C.M, Marcotte, D.J. | | Deposit date: | 2020-02-23 | | Release date: | 2020-12-16 | | Last modified: | 2023-10-11 | | Method: | X-RAY DIFFRACTION (1.4 Å) | | Cite: | Discovery of BIIB068: A Selective, Potent, Reversible Bruton's Tyrosine Kinase Inhibitor as an Orally Efficacious Agent for Autoimmune Diseases.
J.Med.Chem., 63, 2020
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6TSE
 | | Crystal Structure of 1-methylindoline-2,3-dione covalently bound to the PH domain of Bruton's tyrosine kinase mutant R28C | | Descriptor: | 1-methylindole-2,3-dione, MAGNESIUM ION, Tyrosine-protein kinase BTK, ... | | Authors: | Brear, P, Wagstaff, J, Hyvonen, M. | | Deposit date: | 2019-12-20 | | Release date: | 2020-11-25 | | Last modified: | 2024-01-24 | | Method: | X-RAY DIFFRACTION (1.41 Å) | | Cite: | Crystal Structure of 1-methylindoline-2,3-dione covalently bound to the PH domain of Bruton's tyrosine kinase mutant R28C
To Be Published
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6OMU
 | | Structure of human Bruton's Tyrosine Kinase in complex with Evobrutinib | | Descriptor: | 1-[4-({[6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl]amino}methyl)piperidin-1-yl]prop-2-en-1-one, CHLORIDE ION, Tyrosine-protein kinase BTK | | Authors: | Mochalkin, I, Gardberg, A.S. | | Deposit date: | 2019-04-19 | | Release date: | 2019-08-14 | | Last modified: | 2023-10-11 | | Method: | X-RAY DIFFRACTION (1.41 Å) | | Cite: | Discovery of Evobrutinib: An Oral, Potent, and Highly Selective, Covalent Bruton's Tyrosine Kinase (BTK) Inhibitor for the Treatment of Immunological Diseases.
J.Med.Chem., 62, 2019
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5P9M
 | | BTK1 BINDS COVALENTLY TO HY-15771 ONO-4059 | | Descriptor: | 6-azanyl-9-[(3~{R})-1-[(~{E})-but-2-enoyl]pyrrolidin-3-yl]-7-(4-phenoxyphenyl)purin-8-one, DIMETHYL SULFOXIDE, Tyrosine-protein kinase BTK | | Authors: | Gardberg, A.S. | | Deposit date: | 2016-09-20 | | Release date: | 2017-05-24 | | Last modified: | 2021-11-17 | | 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
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6DI5
 | | CRYSTAL STRUCTURE OF BTK IN COMPLEX WITH COVALENT INHIBITOR | | Descriptor: | 2-(4-phenoxyphenoxy)-6-[(1S,4S)-5-propanoyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]pyridine-3-carboxamide, DIMETHYL SULFOXIDE, Tyrosine-protein kinase BTK | | 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
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6O8I
 | | BTK In Complex With Inhibitor | | Descriptor: | 4-[(3S)-3-{[(2E)-but-2-enoyl]amino}piperidin-1-yl]-5-fluoro-2,3-dimethyl-1H-indole-7-carboxamide, Tyrosine-protein kinase BTK | | Authors: | Pokross, M, Tebben, A.J, Watterson, S.H. | | Deposit date: | 2019-03-11 | | Release date: | 2019-04-03 | | Last modified: | 2019-04-24 | | Method: | X-RAY DIFFRACTION (1.42 Å) | | Cite: | Discovery of Branebrutinib (BMS-986195): A Strategy for Identifying a Highly Potent and Selective Covalent Inhibitor Providing Rapid in Vivo Inactivation of Bruton's Tyrosine Kinase (BTK).
J. Med. Chem., 62, 2019
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8FLL
 | | Crystal structure of BTK kinase domain in complex with pirtobrutinib | | Descriptor: | 2-[BIS-(2-HYDROXY-ETHYL)-AMINO]-2-HYDROXYMETHYL-PROPANE-1,3-DIOL, GLYCEROL, SULFATE ION, ... | | Authors: | Cedervall, E.P, Morales, T.H, Allerston, C.K. | | Deposit date: | 2022-12-21 | | Release date: | 2023-03-01 | | Last modified: | 2024-05-22 | | Method: | X-RAY DIFFRACTION (1.498 Å) | | Cite: | Preclinical characterization of pirtobrutinib, a highly selective, noncovalent (reversible) BTK inhibitor.
Blood, 142, 2023
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6BKW
 | | BTK complex with compound 12 | | Descriptor: | GLYCEROL, 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, SULFATE ION, ... | | Authors: | Kiefer, J.R, Eigenbrot, C, Yu, C.L. | | Deposit date: | 2017-11-09 | | Release date: | 2018-11-07 | | Last modified: | 2019-03-27 | | 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., 33, 2019
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5T18
 | | 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: | 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, Tyrosine-protein kinase BTK | | Authors: | Muckelbauer, J.K. | | Deposit date: | 2016-08-18 | | Release date: | 2017-03-08 | | Last modified: | 2024-03-06 | | 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
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7N4Q
 | | Bruton's tyrosine kinase in complex with compound 45 | | Descriptor: | (2R)-2-(3-chloro-5-fluoroanilino)-2-cyclopropyl-N-[(3R)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-3-yl]acetamide, Tyrosine-protein kinase BTK | | Authors: | Metrick, C.M, Marcotte, D.J. | | Deposit date: | 2021-06-04 | | Release date: | 2022-05-18 | | Last modified: | 2023-10-18 | | Method: | X-RAY DIFFRACTION (1.5 Å) | | Cite: | Utilizing structure based drug design and metabolic soft spot identification to optimize the in vitro potency and in vivo pharmacokinetic properties leading to the discovery of novel reversible Bruton's tyrosine kinase inhibitors.
Bioorg.Med.Chem., 44, 2021
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6W07
 | | Bruton's tyrosine kinase in complex with compound 1 | | Descriptor: | DIMETHYL SULFOXIDE, Tyrosine-protein kinase BTK, ~{N}-[[2-methyl-4-[2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]phenyl]methyl]-3-propan-2-yloxy-azetidine-1-carboxamide | | Authors: | Metrick, C.M, Marcotte, D.J. | | Deposit date: | 2020-02-29 | | Release date: | 2020-12-16 | | Last modified: | 2023-10-11 | | Method: | X-RAY DIFFRACTION (1.51 Å) | | Cite: | Discovery of BIIB068: A Selective, Potent, Reversible Bruton's Tyrosine Kinase Inhibitor as an Orally Efficacious Agent for Autoimmune Diseases.
J.Med.Chem., 63, 2020
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7R61
 | | BTK in complex with 25A | | Descriptor: | 5-{(3S)-1-[(Z)-iminomethyl]piperidin-3-yl}-2-(4-phenoxyphenoxy)pyridine-3-carboxamide, DIMETHYL SULFOXIDE, Tyrosine-protein kinase BTK | | Authors: | Gardberg, A. | | Deposit date: | 2021-06-22 | | Release date: | 2021-10-06 | | Last modified: | 2023-10-18 | | Method: | X-RAY DIFFRACTION (1.52 Å) | | Cite: | Discovery of Covalent Bruton's Tyrosine Kinase Inhibitors with Decreased CYP2C8 Inhibitory Activity.
Chemmedchem, 16, 2021
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7LTZ
 | | Bruton's tyrosine kinase in complex with compound 51 | | Descriptor: | 1-~{tert}-butyl-~{N}-[(5~{R})-8-[2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]-2-(oxetan-3-yl)-1,3,4,5-tetrahydro-2-benzazepin-5-yl]-1,2,3-triazole-4-carboxamide, 2,3-DIHYDROXY-1,4-DITHIOBUTANE, ACETATE ION, ... | | Authors: | Metrick, C.M, Marcotte, D.J. | | Deposit date: | 2021-02-20 | | Release date: | 2022-01-12 | | Last modified: | 2023-10-18 | | Method: | X-RAY DIFFRACTION (1.53 Å) | | Cite: | Discovery and Preclinical Characterization of BIIB091, a Reversible, Selective BTK Inhibitor for the Treatment of Multiple Sclerosis.
J.Med.Chem., 65, 2022
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4OT5
 | | 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: | 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, Tyrosine-protein kinase BTK | | Authors: | Kuglstatter, A, Wong, A. | | Deposit date: | 2014-02-13 | | Release date: | 2014-05-14 | | Last modified: | 2023-09-20 | | 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
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8FLH
 | | Bruton's tyrosine kinase in complex with an orthosteric inhibitor | | Descriptor: | 2-(3,5-dichloroanilino)-1-{(3R)-3-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]azepan-1-yl}ethan-1-one, DIMETHYL SULFOXIDE, Tyrosine-protein kinase BTK | | Authors: | Metrick, C.M, Marcotte, D.J. | | Deposit date: | 2022-12-21 | | Release date: | 2023-03-01 | | Last modified: | 2024-05-22 | | Method: | X-RAY DIFFRACTION (1.55 Å) | | Cite: | Discovery of structural diverse reversible BTK inhibitors utilized to develop a novel in vivo CD69 and CD86 PK/PD mouse model.
Bioorg.Med.Chem.Lett., 80, 2023
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7N5R
 | | Fragment-Based Discovery of a Novel Bruton's Tyrosine Kinase Inhibitor | | Descriptor: | 1,2-ETHANEDIOL, 5-phenyl-2,4-dihydro-3H-1,2,4-triazol-3-one, DIMETHYL SULFOXIDE, ... | | Authors: | Dougan, D.R, Lawson, J.D. | | Deposit date: | 2021-06-06 | | Release date: | 2021-09-08 | | Last modified: | 2023-10-18 | | Method: | X-RAY DIFFRACTION (1.55 Å) | | Cite: | Discovery of the Bruton's Tyrosine Kinase Inhibitor Clinical Candidate TAK-020 ( S )-5-(1-((1-Acryloylpyrrolidin-3-yl)oxy)isoquinolin-3-yl)-2,4-dihydro-3 H -1,2,4-triazol-3-one, by Fragment-Based Drug Design.
J.Med.Chem., 64, 2021
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6W06
 | | Bruton's tyrosine kinase in complex with compound 6 | | Descriptor: | 2,3-DIHYDROXY-1,4-DITHIOBUTANE, 4-~{tert}-butyl-~{N}-[[4-(7~{H}-pyrrolo[2,3-d]pyrimidin-4-yl)phenyl]methyl]benzamide, DIMETHYL SULFOXIDE, ... | | Authors: | Metrick, C.M, Marcotte, D.J. | | Deposit date: | 2020-02-29 | | Release date: | 2020-12-16 | | Last modified: | 2023-10-11 | | Method: | X-RAY DIFFRACTION (1.55 Å) | | Cite: | Discovery of BIIB068: A Selective, Potent, Reversible Bruton's Tyrosine Kinase Inhibitor as an Orally Efficacious Agent for Autoimmune Diseases.
J.Med.Chem., 63, 2020
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4OTQ
 | | 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: | 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, Tyrosine-protein kinase BTK | | Authors: | Kuglstatter, A, Wong, A. | | Deposit date: | 2014-02-14 | | Release date: | 2014-05-14 | | Last modified: | 2023-09-20 | | 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
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5BQ0
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8EJB
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5VFI
 | | Bruton's tyrosine kinase (BTK) with GDC-0853 | | Descriptor: | 1,2-ETHANEDIOL, 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, SULFATE ION, ... | | Authors: | Steinbacher, S, Eigenbrot, C. | | Deposit date: | 2017-04-07 | | Release date: | 2018-02-28 | | Last modified: | 2024-03-13 | | 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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5J87
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4Z3V
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