- Discovery of Novel Potent VEGFR-2 Inhibitors Exerting Significant Antiproliferative Activity against Cancer Cell Lines
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Computational and experimental studies were applied to the discovery of a series of novel vascular endothelial growth factor receptor 2 (VEGFR-2) inhibitors. Eight compounds exhibited nanomolar IC50 values against VEGFR-2, and compounds 6, 19,
- Zhang, Yanmin,Chen, Yadong,Zhang, Danfeng,Wang, Lu,Lu, Tao,Jiao, Yu
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Read Online
- PROTEIN DEGRADATION TARGETING COMPOUND, ANTI-TUMOR APPLICATION, INTERMEDIATE THEREOF AND USE OF INTERMEDIATE
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The present disclosure relates to compounds of formula (I) and their anti-tumor uses, and their intermediates of formula (III), intermediates of formula (IV), and uses of the intermediates. The compound of formula (I) has a degrading effect on a specific target protein, which is mainly composed of three parts. The first part is a small molecule compound (SMBP, Small Molecules Binding Protein) that can bind to a protein, the second part LIN is a linker, and the three-part ULM is a ubiquitin ligand (ULM, Ubiquitin Ligase Binding Moiety), wherein SMBP is covalently bound to LIN, and LIN is covalently bound to ULM. A series of compounds designed and synthesized in the present disclosure have a wide range of pharmacological activities, including the functions of degrading specific proteins and/or inhibiting activities of specific proteins, and thus can be used in related tumor treatments.
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Paragraph 0386-0387
(2021/02/18)
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- KINASE INHIBITORS AND USES THEREOF
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This invention described herein relates to compounds of general formula (I) : (I), in which variable groups are as defined herein, and to their preparation and use. Uses for the compounds and for compositions containing them include treatment of cancer and other diseases mediated by protein kinases, such as Bcr-Abl kinase, and mutants thereof, such as the T315I mutant.
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Page/Page column 46; 47
(2020/10/21)
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- Alkynyl pyrimidine or alkynyl pyridine compound as well as composition and application thereof
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The invention relates to alkynyl pyrimidine or alkynyl pyridine compounds represented by a formula (I) or pharmaceutically acceptable salts, isomers, solvates, crystals or prodrugs thereof. The invention also discloses a pharmaceutical composition contain
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Paragraph 0124-0126
(2020/08/18)
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- O-AMINOHETEROARYL ALKYNYL-CONTAINING COMPOUND, PREPARATION METHOD THEREFOR, AND USE THEREOF
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An o-aminoheteroaryl alkynyl-containing compound, a preparation method therefor and a use thereof. The o-aminoheteroaryl alkynyl-containing compound has a structure represented by formula (I), and the compound of formula (I) has advantages of a high FGFR
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Paragraph 0033
(2020/01/08)
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- Substituted diaryl amide compound as well as preparation method and application thereof
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The invention provides a substituted diaryl amide compound as well as a preparation method and application thereof. The substituted diaryl amide compound or a pharmaceutically acceptable salt thereofis of a structure of a formula [1] (the formula is shown
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Paragraph 0130; 0133; 0134
(2019/04/04)
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- IRE1 SMALL MOLECULE INHIBITORS
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Provided herein are small molecule inhibitors for the targeting or IRE1 protein family members. Binding may be direct or indirect. Further provided herein are methods of using IRE1 small molecule inhibitors for use in treating or ameliorating cancer in a
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Paragraph 00216
(2018/06/22)
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- NOVEL INHIBITORS OF MAP4K1
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The invention relates to novel inhibitors of MAP4K1 (HPK1) useful for the treatment of diseases or disorders characterised by dysregulation of the signal transduction pathways associated with MAPK activation, including hyperproliferative diseases, diseases of immune system dysfunction, inflammatory disorders, neurological diseases, and cardiovascular diseases. The invention further relates to pharmaceutical compositions comprising the same and methods of treatment of said diseases and disorders. The inhibitors are of formula (I) wherein the definitions for A, D, E, F, R5, R6, R7, Z, ring Q, n, x and y are as given in the application.
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Page/Page column 66; 67
(2018/12/13)
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- Benzamide compounds containing acetenyl group
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The invention provides acetenyl group-containing benzamide compounds as shown in a formula (I) and used for treating or preventing diseases related to protein kinase, and medicinal salts or configurational isomers thereof. A connection group L, a ring A and substituents R, R, R, R and R in the formula (I) are as defined in the specification. The invention also discloses a preparation method and a pharmaceutical composition of the compounds as shown in the formula (I), and application of the compounds to preparation or prevention of drugs used for preventing diseases related to protein kinase.
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Paragraph 0070; 0071
(2017/07/22)
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- NEW SUBSTITUTED CYANOINDOLINE DERIVATIVES AS NIK INHIBITORS
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The present invention relates to pharmaceutical agents of formula (I) useful for therapy and/or prophylaxis in a mammal, and in particular to inhibitors of NF- KB-inducing kinase (NIK - also known as MAP3K14) useful for treating diseases such as cancer, inflammatory disorders, metabolic disorders and autoimmune disorders. The invention is also directed to pharmaceutical compositions comprising such compounds, and to the use of such compounds or pharmaceutical compositions for the prevention or treatment of diseases such as cancer, inflammatory disorders, metabolic disorders including obesity and diabetes, and autoimmune disorders.
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Page/Page column 270
(2017/08/20)
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- Design, synthesis and evaluation of derivatives based on pyrimidine scaffold as potent Pan-Raf inhibitors to overcome resistance
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Simutaneous targeting all Raf isoforms offers the prospect of enhanced efficacy as well as reduced potential for resistance. Described herein is the discovery and characterization of a series of pyrimidine scaffold with DFG-out conformation as potent Pan-Raf inhibitors. Among them, I-41 with excellent Pan-Raf potency demonstrates inhibitory activity against BRafWTphenotypic melanoma and BRafV600Ephenotypic colon cells. The western blot results for the Erk inhibition in human melanoma SK-Mel-2?cell lines showed I-41 inhibited the proliferation of SK-Mel-2?cell lines without paradoxical activation of Erk, which supported I-41 may become a good candidate compound to overcome the resistance of melanoma against the current BRafV600Einhibitor therapy. I-41 also have a favorable pharmacokinetic profile in rat. Synthesis, SAR, lead selection, and evaluation of the key compounds studies are described.
- Wang, Lu,Zhang, Qing,Zhu, Gaoyuan,Zhang, Zhimin,Zhi, Yanle,Zhang, Li,Mao, Tianxiao,Zhou, Xiang,Chen, Yadong,Lu, Tao,Tang, Weifang
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supporting information
p. 86 - 106
(2017/03/02)
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- Rational design, synthesis, and biological evaluation of Pan-Raf inhibitors to overcome resistance
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Selective BRafV600E inhibitors with DFG-in conformation have been proven effective against a subset of melanoma. However, representative inhibitor vemurafenib rapidly acquires resistance in the BRafWT cells through a CRaf or BRafWT dependent manner. Simultaneous targeting of all subtypes of Raf proteins offers the prospect of enhanced efficacy as well as reduced potential for acquired resistance. Herein, we describe the design and characterization of a series of compounds I-01-I-22, based on a pyrimidine scaffold with DFG-out conformation as Pan-Raf inhibitors. Among them, I-15 binds to all Raf protomers with IC50 values of 12.6 nM (BRafV600E), 30.1 nM (ARaf), 19.7 nM (BRafWT) and 17.5 nM (CRaf) and demonstrates cellular activity against BRafWT phenotypic melanoma and BRafV600E phenotypic colorectal cancer cells. The western blot results for the P-Erk inhibition in human melanoma SK-Mel-2 cell line showed that I-15 inhibited the proliferation of the SK-Mel-2 cell line at concentrations as low as 400 nM, without paradoxical activation of Erk as vemurafenib, which supported that I-15 may become a good candidate compound to overcome the resistance of melanoma induced by vemurafenib. I-15 also has a favorable pharmacokinetic profile in rats. Rational design, synthesis, SAR, lead selection and evaluation of the key compounds studied are described.
- Wang, Lu,Zhu, Gaoyuan,Zhang, Qing,Duan, Chunqi,Zhang, Yanmin,Zhang, Zhimin,Zhou, Yujun,Lu, Tao,Tang, Weifang
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supporting information
p. 3455 - 3465
(2017/04/26)
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- Potent Pan-Raf and Receptor Tyrosine Kinase Inhibitors Based on a Cyclopropyl Formamide Fragment Overcome Resistance
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While selective BRafV600E inhibitors have been proven effective clinically, acquired resistance rapidly develops through reactivation of the mitogen-activated protein kinase (MAPK) pathway. Simultaneous targeting of multiple nodes in the pathway offers the prospect of enhanced efficacy as well as reduced potential for acquired resistance. Replacement pyridine group of Y-1 by a cyclopropyl formamide group afforded I-01 as a novel multitargeted kinase inhibitor template. I-01 displayed enzyme potency against Pan-Raf and receptor tyrosine kinases (RTKs). Based on the binding mode of I-01, analogues I-02-I-18 were designed and synthesized. The most promising compound I-16 potently inhibits all subtypes of Rafs with IC50 values of 3.49 (BRafV600E), 8.86 (ARaf), 5.78 (BRafWT), and 1.65 nM (CRaf), respectively. I-16 not only exhibit comparable antiproliferative activities with positive control compounds against HepG2, SW579, MV4-11, and COLO205 cell lines, but also suppress the proliferation of melanoma SK-MEL-2 harboring overexpressed BRafWT with IC50 values of 0.93 μM. The Western blot results for the ERK inhibition in human melanoma SK-MEL-2 cell lines show that I-16 inhibits the proliferation of SK-MEL-2 cell lines without paradoxical activation of ERK, which support the hypothesis that the inhibition of Pan-Raf and RTKs might be a tractable strategy to overcome the resistance of melanoma induced by the therapy with the current selective BRafV600E inhibitors.
- Zhang, Yanmin,Wang, Lu,Zhang, Qing,Zhu, Gaoyuan,Zhang, Zhimin,Zhou, Xiang,Chen, Yadong,Lu, Tao,Tang, Weifang
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p. 1439 - 1452
(2017/06/30)
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- BCR-ABL DIPLOID INHIBITOR, PREPARATION METHOD THEREFOR, AND USES THEREOF
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Disclosed are compounds or pharmaceutically acceptable salts thereof having the following general formula: R-Linker-R. The compounds or pharmaceutically acceptable salts thereof provided by the present invention are used as Bcr-Abl diploid inhibitors, whi
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Paragraph 0041
(2017/03/08)
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- Preparation and application of triazole compound
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The invention provides preparation and application of a triazole compound. A preparation method comprises the following steps: enabling a first compound, namely 1-methyl-4-nitryl-2-(trifluoromethyl) benzene to react under the action of NBS, BPO and CCl4 s
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Paragraph 0052; 0053; 0054
(2017/07/22)
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- Inhibitors to Overcome Secondary Mutations in the Stem Cell Factor Receptor KIT
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In modern cancer therapy, the use of small organic molecules against receptor tyrosine kinases (RTKs) has been shown to be a valuable strategy. The association of cancer cells with dysregulated signaling pathways linked to RTKs represents a key element in
- Kaitsiotou, Helena,Keul, Marina,Hardick, Julia,Mühlenberg, Thomas,Ketzer, Julia,Ehrt, Christiane,Krüll, Jasmin,Medda, Federico,Koch, Oliver,Giordanetto, Fabrizio,Bauer, Sebastian,Rauh, Daniel
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p. 8801 - 8815
(2017/11/15)
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- 3-ACETYLENYL-PYRAZOLE-PYRIMIDINE DERIVATIVE, AND PREPARATION METHOD THEREFOR AND USES THEREOF
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The present invention relates to the field of chemical and medicine, more particularly, 3-ethynylpyrazolopyrimidine derivatives and their preparation methods and uses. The invention provides a 3-ethynylpyrazolopyrimidine derivative, and the structure is shown in formula I. The present invention also provides preparation methods and use of 3-ethynylpyrazolopyrimidine derivatives, comprising the compounds and derivatives, and their pharmaceutical compositions for the use of the treatment and prevention of tumors.
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Paragraph 0193; 0194
(2017/11/10)
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- Discovery of a Nanomolar Multikinase Inhibitor (KST016366): A New Benzothiazole Derivative with Remarkable Broad-Spectrum Antiproliferative Activity
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Herein we report the discovery of compound 6 [KST016366; 4-((2-(3-(4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)ureido)benzo[d]thiazol-6-yl)oxy)picolinamide] as a new potent multikinase inhibitor through minor structural modification of our
- El-Damasy, Ashraf Kareem,Cho, Nam-Chul,Nam, Ghilsoo,Pae, Ae Nim,Keum, Gyochang
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supporting information
p. 1587 - 1595
(2016/08/28)
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- Design, synthesis and biological evaluation of coumarin derivatives as novel acetylcholinesterase inhibitors that attenuate H2O2-induced apoptosis in SH-SY5Y cells
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A novel series of coumarin derivatives were designed, synthesized and investigated for inhibition of cholinesterase, including acetyl cholinesterase (AChE) and butyrylcholinesterase (BuChE). This biological study showed that these compounds containing piperazine ring had significant inhibition activities on AChE rather than BuChE. Further study suggested that 9x, as one of this kind of structure derivative, showed the strongest inhibition activity on AChE with an IC50 value of 34?nM. Moreover, molecular docking, flow cytometry (FCM), and western blot assay suggested that 9x could induce cytoprotective autophagy to attenuate H2O2-induced cell death in human neuroblastoma SH-SY5Y cells. These findings highlight a new approach for the development of a novel potential neuroprotective compound targeting AChE with autophagy-inducing activity in future Alzheimer's disease (AD) therapy.
- Yao, Dahong,Wang, Jing,Wang, Guan,Jiang, Yingnan,Shang, Lei,Zhao, Yuqian,Huang, Jian,Yang, Shilin,Wang, Jinhui,Yu, Yamei
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p. 112 - 123
(2016/08/01)
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- PROCESSES FOR MAKING PONATINIB AND INTERMEDIATES THEREOF
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Methods are disclosed for making 3-(imidazo[1,2-b]pyridazin-3-ylethynyl)-4-methyl-N-[4-[(4-methylpiperazin-l-yl)methyl]-3-(trifluoromethyl)phenyl]benzamide, intermediates and pharmaceutically acceptable salts thereof.
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Page/Page column 7; 8
(2016/12/26)
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- BCR-ABL kinase inhibitor and its application (by machine translation)
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The present invention relates to the field of chemical medicines, in particular to compounds as represented by formula I having BCR-ABL kinase inhibitory activity, or pharmaceutically acceptable salt, isomer, solvate, crystal or prodrug thereof, and pharmaceutical composition containing the compounds, and application of the compounds or compositions in drug preparation. The compounds of the present invention have strong inhibitory effect on BCR-ABL kinase, and can be used to treat diseases such as tumors.
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Paragraph 0087
(2017/03/28)
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- BCR-ABL TYROSINE-KINASE LIGANDS CAPABLE OF DIMERIZING IN AN AQUEOUS SOLUTION, AND METHODS OF USING SAME
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Described herein are monomers capable of forming a biologically useful multimer when in contact with one, two, three or more other monomers in an aqueous media. In one aspect, such monomers may be capable of binding to another monomer in an aqueous media (e.g. invivo) to form a multimer (e.g. a dimer). Contemplated monomers may include a ligand moiety, a linker element, and a connector element that joins the ligand moiety and the linker element. In an aqueous media, such contemplated monomers may join together via each linker element and may thus be capable of modulating one or more biomolecules substantially simultaneously, e.g., modulate two or more binding sites on a Bcr-Abl tyrosine kinase.
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Paragraph 00605; 00612; 00613
(2015/07/23)
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- ISOQUINOLINE-5-CARBOXAMIDE DERIVATIVE HAVING INHIBITORY ACTIVITY FOR PROTEIN KINASE
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A compound selected from the group consisting of an isoquinoline-5-carboxamide derivative of formula (I), a pharmaceutically acceptable salt, an isomer, a hydrate and a solvate thereof is effective for the prevention or treatment of diseases associated with abnormal cell growth, which are caused by abnormal activation of a protein kinases.
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Paragraph 0088
(2015/06/03)
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- ISOQUINOLINE-5-CARBOXAMIDE DERIVATIVE HAVING INHIBITORY ACTIVITY FOR PROTEIN KINASE
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A compound selected from the group consisting of an isoquinoline-5-carboxamide derivative of formula (I), a pharmaceutically acceptable salt, an isomer, a hydrate and a solvate thereof is effective for the prevention or treatment of diseases associated with abnormal cell growth, which are caused by abnormal activation of a protein kinases.
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Paragraph 0185-0187
(2015/07/15)
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- THIENO[3,2-D]PYRIMIDINE DERIVATIVES HAVING INHIBITORY ACTIVITY FOR PROTEIN KINASES
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Provided are a thieno[3,2-d]pyrimidine derivative of formula (I) or a pharmaceutically acceptable salt thereof having inhibitory activity for protein kinase, and a pharmaceutical composition comprising same for prevention and treatment of abnormal cell growth diseases.
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Paragraph 0243; 0244; 0245
(2015/01/06)
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- Protein Kinase Inhibitors
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The present invention relates to compounds of Formula I: as well as pharmaceutically acceptable salts, hydrates, isomers, or solvates thereof, wherein the variables are described herein. The present invention further relates to pharmaceutical compositions which comprise the compounds of Formula I, and to methods for inhibiting protein kinase and methods of treating diseases, such as cancers, inflammation.
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Paragraph 0294; 0354; 0355
(2014/02/16)
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- PROCESSES FOR MAKING PONATINIB AND INTERMEDIATES THEREOF
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Novel synthetic approaches to make 3-(imidazo[1,2-b]pyridazin-3-ylethynyl)-4-methyl-N-[4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]benzamide, intermediates and pharmaceutically acceptable salts thereof are provided.
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Paragraph 0074; 0075
(2014/12/09)
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- FUSED TRICYCLIC UREA COMPOUNDS AS RAF KINASE AND/OR RAF KINASE DIMER INHIBITORS
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Provided are certain fused tricyclic urea compounds and salts thereof, compositions thereof, and methods of use therefor.
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Page/Page column 80
(2015/01/16)
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- THIENO[3,2-d]PYRIMIDINE DERIVATIVES HAVING INHIBITORY ACTIVITY ON PROTEIN KINASES
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The present invention relates to a thieno[3,2-d]pyrimidine derivative of formula (I), or a pharmaceutically acceptable salt, hydrate or solvate thereof, which has an excellent inhibitory activity on protein kinases, and a pharmaceutical composition comprising the same is effective in preventing or treating abnormal cell growth diseases.
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Paragraph 0340-0342
(2013/03/26)
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- THIENO[3,2-d]PYRIMIDINE DERIVATIVES HAVING INHIBITORY ACTIVITY FOR PROTEIN KINASES
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Provided are a thieno[3,2-d]pyrimidine derivative of formula (I) or a pharmaceutically acceptable salt thereof having inhibitory activity for protein kinase, and a pharmaceutical composition comprising same for prevention and treatment of abnormal cell growth diseases
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Page/Page column 36
(2013/07/19)
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- Small-molecule inducer of β cell proliferation identified by high-throughput screening
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The identification of factors that promote β cell proliferation could ultimately move type 1 diabetes treatment away from insulin injection therapy and toward a cure. We have performed high-throughput, cell-based screens using rodent β cell lines to ident
- Shen, Weijun,Tremblay, Matthew S.,Deshmukh, Vishal A.,Wang, Weidong,Filippi, Christophe M.,Harb, George,Zhang, You-Qing,Kamireddy, Anwesh,Baaten, Janine E,Jin, Qihui,Wu, Tom,Swoboda, Jonathan G.,Cho, Charles Y.,Li, Jing,Laffitte, Bryan A.,McNamara, Peter,Glynne, Richard,Wu, Xu,Herman, Ann E.,Schultz, Peter G.
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supporting information
p. 1669 - 1672
(2013/04/23)
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- METHODS AND COMPOSITIONS FOR RAF KINASE MEDIATED DISEASES
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The invention discloses methods and compositions for treating or preventing RAF kinase mediated diseases or conditions by administering a compound of Formula 1: or a pharmaceutically acceptable salt, solvate or hydrate thereof, wherein the variables are defined as herein.
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Page/Page column 56
(2013/11/18)
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- THIENO[3,2-d]PYRIMIDINE DERIVATIVES HAVING INHIBITORY ACTIVITY ON PROTEIN KINASES
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The present invention relates to a thieno[3,2-d]pyrimidine derivative of formula (I), or a pharmaceutically acceptable salt, hydrate or solvate thereof, which has an excellent inhibitory activity on protein kinases, and a pharmaceutical composition comprising the same is effective in preventing or treating abnormal cell growth diseases.
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Page/Page column 45; 46
(2011/08/21)
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- Discovery of 3-[2-(imidazo[1,2- b ]pyridazin-3-yl)ethynyl]-4-methyl- N -{4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl}benzamide (AP24534), a potent, orally active pan-inhibitor of breakpoint cluster region-abelson (BCR-ABL) kinase including the T315I gatekeeper mutant
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In the treatment of chronic myeloid leukemia (CML) with BCR-ABL kinase inhibitors, the T315I gatekeeper mutant has emerged as resistant to all currently approved agents. This report describes the structure-guided design of a novel series of potent pan-inhibitors of BCR-ABL, including the T315I mutation. A key structural feature is the carbon-carbon triple bond linker which skirts the increased bulk of Ile315 side chain. Extensive SAR studies led to the discovery of development candidate 20g (AP24534), which inhibited the kinase activity of both native BCR-ABL and the T315I mutant with low nM IC 50s, and potently inhibited proliferation of corresponding Ba/F3-derived cell lines. Daily oral administration of 20g significantly prolonged survival of mice injected intravenously with BCR-ABLT315I expressing Ba/F3 cells. These data, coupled with a favorable ADME profile, support the potential of 20g to be an effective treatment for CML, including patients refractory to all currently approved therapies.
- Huang, Wei-Sheng,Metcalf, Chester A.,Sundaramoorthi, Raji,Wang, Yihan,Zou, Dong,Thomas, R. Mathew,Zhu, Xiaotian,Cai, Lisi,Wen, David,Liu, Shuangying,Romero, Jan,Qi, Jiwei,Chen, Ingrid,Banda, Geetha,Lentini, Scott P.,Das, Sasmita,Xu, Qihong,Keats, Jeff,Wang, Frank,Wardwell, Scott,Ning, Yaoyu,Snodgrass, Joseph T.,Broudy, Marc I.,Russian, Karin,Zhou, Tianjun,Commodore, Lois,Narasimhan, Narayana I.,Mohemmad, Qurish K.,Iuliucci, John,Rivera, Victor M.,Dalgarno, David C.,Sawyer, Tomi K.,Clackson, Tim,Shakespeare, William C.
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experimental part
p. 4701 - 4719
(2010/10/03)
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- AMINOPYRIMIDINE COMPOUNDS AND THEIR SALTS, PROCESS FOR PREPARATION AND PHARMACEUTICAL USE THEREOF
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The present invention provides aminopyrimidine compounds of formula (I) and their salts, wherein R1, R2, R3, R4, R5, R6, Q, Z, L, m, n are defined as the description, the methods for preparation thereof, the uses thereof and the pharmaceutical compositions comprising the effective amount of compounds of formula (I). The compounds of formula (I) and their salts can be used as protein kinase inhibitors.
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Page/Page column 12-13
(2008/06/13)
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- BICYCLIC HETEROARYL COMPOUNDS
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This invention relates to compounds of the general formula (I) in which the variable groups are as defined herein, and to their preparation and use.
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Page/Page column 65-66
(2008/06/13)
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- COMPOUNDS AND COMPOSITIONS AS PROTEIN KINASE INHIBITORS
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The invention provides a novel class of compounds, pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent diseases or disorders associated with abnormal or deregulated kinase activity, particularly diseases or disorders that involve abnormal activation of Abl, Bcr-Abl, Bmx, BTK, b-RAF, c RAF, CSK, cSRC, Fes, FGFR3, Flt3, IKKα, IKKβ, JNK1α1, JNK2α2, Lck, Met, MKK4, MKK6, p70S6K, PAK2, PDGFRα, PKA, PKCα, PKD2, ROCK-II, Ros, Rsk1, SAPK2α, SAPK2β, SAPK3, SAPK4, SGK, Syk, Tie2 and TrkB kinases.
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Page/Page column 31-32
(2008/06/13)
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