Name: EW-7197
CAS#: 1352608-82-2
Chemical Formula: C22H18FN7
Exact Mass: 399.1608
Molecular Weight: 399.4334
Elemental Analysis: C, 66.15; H, 4.54; F, 4.76; N, 24.55
EOS Med Chem produce EW-7197 1352608-82-2 in GMP plant, C-GMP standard, now COA, NMR, HPLC, MS is ok.
EW-7197 1352608-82-2 Intermediates, EOS Med Chem have 8; EW-7197 1352608-82-2 Impurity we have 10, all from GMP, FDA plant.
Now EW-7197 1352608-82-2 DMF document is preparing.
Until 2016, Aug, EW-7197 1352608-82-2 more than produced 25kg API, 120kg Intermediates
GMP PRODUCE:
Alectinib;Veliparib;Acalabrutinib;Venetoclax;Sotagliflozin;Ledipasvir;LX1606;Anacetrapib;Abemaciclib
TEW-7197 Intermediates N-(5-iodopyridin-2-yl)-N,N-dimethylmethanediamine
TEW-7197 Intermediates 6-iodo-[1,2,4]triazolo[1,5-a]pyridine 614750-84-4
TEW-7197 Intermediates [1,2,4]triazolo[1,5-a]pyridine-6-carbaldehyde 614750-81-1
TEW-7197 Intermediates diphenyl ((6-methylpyridin-2-yl)(phenylamino)methyl)phosphonate 614750-85-5
TEW-7197 Intermediates 2-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-1-(6-methylpyridin-2-yl)ethanone 614750-82-2
TEW-7197 Intermediates 1-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-2-(6-methylpyridin-2-yl)ethane-1,2-dione 356560-84-4
TEW-7197 Intermediates 6-(2-(dimethoxymethyl)-5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine 1352609-89-2
TEW-7197 Intermediates 4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-5-(6-methylpyridin-2-yl)-1H-imidazole-2-carbaldehyde 1352609-91-6
Description: TEW-7197, also known as EW-7197, is and orally bioavailable inhibitor of the serine/threonine kinase, transforming growth factor (TGF)-beta receptor type 1 (TGFBR1), also known as activin receptor-like kinase 5 (ALK5), with potential antineoplastic activity. Upon oral administration, TEW-7197 inhibits the activity of TGFBR1 and prevents TGF-beta/TGFBR1-mediated signaling. This suppresses tumor growth in TGFBR1-overexpressing tumor cells. TGFBR1, which is overexpressed in a variety of tumor cell types, plays a key role in tumor cell proliferation.
Synonym: TEW-7197; TEW 7197; TEW7197; EW-7197; EW 7197; EW7197.
IUPAC/Chemical Name: N-((4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-5-(6-methylpyridin-2-yl)-1H-imidazol-2-yl)methyl)-2-fluoroaniline
SMILES Code: FC1=CC=CC=C1NCC2=NC(C3=CN4C(C=C3)=NC=N4)=C(C5=NC(C)=CC=C5)N2
1: Kim MJ, Park SA, Kim CH, Park SY, Kim JS, Kim DK, Nam JS, Sheen YY. TGF-β Type I Receptor Kinase Inhibitor EW-7197 Suppresses Cholestatic Liver Fibrosis by Inhibiting HIF1α-Induced Epithelial Mesenchymal Transition. Cell Physiol Biochem. 2016;38(2):571-88. doi: 10.1159/000438651. PubMed PMID: 26845171.
2: Naka K, Ishihara K, Jomen Y, Jin CH, Kim DH, Gu YK, Jeong ES, Li S, Krause DS, Kim DW, Bae E, Takihara Y, Hirao A, Oshima H, Oshima M, Ooshima A, Sheen YY, Kim SJ, Kim DK. Novel oral transforming growth factor-β signaling inhibitor EW-7197 eradicates CML-initiating cells. Cancer Sci. 2016 Feb;107(2):140-8. doi: 10.1111/cas.12849. PubMed PMID: 26583567; PubMed Central PMCID: PMC4768399.
3: Park SA, Kim MJ, Park SY, Kim JS, Lim W, Nam JS, Yhong Sheen Y. TIMP-1 mediates TGF-β-dependent crosstalk between hepatic stellate and cancer cells via FAK signaling. Sci Rep. 2015 Nov 9;5:16492. doi: 10.1038/srep16492. PubMed PMID: 26549110; PubMed Central PMCID: PMC4637930.
4: Krishnaiah M, Jin CH, Sheen YY, Kim DK. Synthesis and biological evaluation of 5-(fluoro-substituted-6-methylpyridin-2-yl)-4-([1,2,4]triazolo[1,5-a]pyridin-6-yl )imidazoles as inhibitors of transforming growth factor-β type I receptor kinase. Bioorg Med Chem Lett. 2015 Nov 15;25(22):5228-31. doi: 10.1016/j.bmcl.2015.09.058. PubMed PMID: 26483198.
5: Park SY, Kim MJ, Park SA, Kim JS, Min KN, Kim DK, Lim W, Nam JS, Sheen YY. Combinatorial TGF-β attenuation with paclitaxel inhibits the epithelial-to-mesenchymal transition and breast cancer stem-like cells. Oncotarget. 2015 Nov 10;6(35):37526-43. doi: 10.18632/oncotarget.6063. PubMed PMID: 26462028; PubMed Central PMCID: PMC4741946.
6: Park SA, Kim MJ, Park SY, Kim JS, Lee SJ, Woo HA, Kim DK, Nam JS, Sheen YY. EW-7197 inhibits hepatic, renal, and pulmonary fibrosis by blocking TGF-β/Smad and ROS signaling. Cell Mol Life Sci. 2015 May;72(10):2023-39. doi: 10.1007/s00018-014-1798-6. PubMed PMID: 25487606.
7: Son JY, Park SY, Kim SJ, Lee SJ, Park SA, Kim MJ, Kim SW, Kim DK, Nam JS, Sheen YY. EW-7197, a novel ALK-5 kinase inhibitor, potently inhibits breast to lung metastasis. Mol Cancer Ther. 2014 Jul;13(7):1704-16. doi: 10.1158/1535-7163.MCT-13-0903. PubMed PMID: 24817629.
8: Jin CH, Krishnaiah M, Sreenu D, Subrahmanyam VB, Rao KS, Lee HJ, Park SJ, Park HJ, Lee K, Sheen YY, Kim DK. Discovery of N-((4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-5-(6-methylpyridin-2-yl)-1H-imidazol-2 -yl)methyl)-2-fluoroaniline (EW-7197): a highly potent, selective, and orally bioavailable inhibitor of TGF-β type I receptor kinase as cancer immunotherapeutic/antifibrotic agent. J Med Chem. 2014 May 22;57(10):4213-38. doi: 10.1021/jm500115w. PubMed PMID: 24786585.
9: Sheen YY, Kim MJ, Park SA, Park SY, Nam JS. Targeting the Transforming Growth Factor-β Signaling in Cancer Therapy. Biomol Ther (Seoul). 2013 Sep 30;21(5):323-31. doi: 10.4062/biomolther.2013.072. Review. PubMed PMID: 24244818; PubMed Central PMCID: PMC3825194.
10: Yoon JH, Jung SM, Park SH, Kato M, Yamashita T, Lee IK, Sudo K, Nakae S, Han JS, Kim OH, Oh BC, Sumida T, Kuroda M, Ju JH, Jung KC, Park SH, Kim DK, Mamura M. Activin receptor-like kinase5 inhibition suppresses mouse melanoma by ubiquitin degradation of Smad4, thereby derepressing eomesodermin in cytotoxic T lymphocytes. EMBO Mol Med. 2013 Nov;5(11):1720-39. doi: 10.1002/emmm.201302524. Erratum in: EMBO Mol Med. 2014 May;6(5):703. PubMed PMID: 24127404; PubMed Central PMCID: PMC3840488.
CAS#: 1352608-82-2
Chemical Formula: C22H18FN7
Exact Mass: 399.1608
Molecular Weight: 399.4334
Elemental Analysis: C, 66.15; H, 4.54; F, 4.76; N, 24.55
EOS Med Chem produce EW-7197 1352608-82-2 in GMP plant, C-GMP standard, now COA, NMR, HPLC, MS is ok.
EW-7197 1352608-82-2 Intermediates, EOS Med Chem have 8; EW-7197 1352608-82-2 Impurity we have 10, all from GMP, FDA plant.
Now EW-7197 1352608-82-2 DMF document is preparing.
Until 2016, Aug, EW-7197 1352608-82-2 more than produced 25kg API, 120kg Intermediates
GMP PRODUCE:
Alectinib;Veliparib;Acalabrutinib;Venetoclax;Sotagliflozin;Ledipasvir;LX1606;Anacetrapib;Abemaciclib
2016 Mumbai CPHI, Hope to meet!
2016 Barcelona CPHI, Hope to meet!
2016 Korea(한국) CPHI, C40, Welcome!
2016 Shanghai CPHI, W5C47, Welcome!
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TEW-7197 Intermediates N-(5-iodopyridin-2-yl)-N,N-dimethylmethanediamine
TEW-7197 Intermediates 6-iodo-[1,2,4]triazolo[1,5-a]pyridine 614750-84-4
TEW-7197 Intermediates [1,2,4]triazolo[1,5-a]pyridine-6-carbaldehyde 614750-81-1
TEW-7197 Intermediates diphenyl ((6-methylpyridin-2-yl)(phenylamino)methyl)phosphonate 614750-85-5
TEW-7197 Intermediates 2-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-1-(6-methylpyridin-2-yl)ethanone 614750-82-2
TEW-7197 Intermediates 1-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-2-(6-methylpyridin-2-yl)ethane-1,2-dione 356560-84-4
TEW-7197 Intermediates 6-(2-(dimethoxymethyl)-5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine 1352609-89-2
TEW-7197 Intermediates 4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-5-(6-methylpyridin-2-yl)-1H-imidazole-2-carbaldehyde 1352609-91-6
Description: TEW-7197, also known as EW-7197, is and orally bioavailable inhibitor of the serine/threonine kinase, transforming growth factor (TGF)-beta receptor type 1 (TGFBR1), also known as activin receptor-like kinase 5 (ALK5), with potential antineoplastic activity. Upon oral administration, TEW-7197 inhibits the activity of TGFBR1 and prevents TGF-beta/TGFBR1-mediated signaling. This suppresses tumor growth in TGFBR1-overexpressing tumor cells. TGFBR1, which is overexpressed in a variety of tumor cell types, plays a key role in tumor cell proliferation.
Synonym: TEW-7197; TEW 7197; TEW7197; EW-7197; EW 7197; EW7197.
IUPAC/Chemical Name: N-((4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-5-(6-methylpyridin-2-yl)-1H-imidazol-2-yl)methyl)-2-fluoroaniline
SMILES Code: FC1=CC=CC=C1NCC2=NC(C3=CN4C(C=C3)=NC=N4)=C(C5=NC(C)=CC=C5)N2
1: Kim MJ, Park SA, Kim CH, Park SY, Kim JS, Kim DK, Nam JS, Sheen YY. TGF-β Type I Receptor Kinase Inhibitor EW-7197 Suppresses Cholestatic Liver Fibrosis by Inhibiting HIF1α-Induced Epithelial Mesenchymal Transition. Cell Physiol Biochem. 2016;38(2):571-88. doi: 10.1159/000438651. PubMed PMID: 26845171.
2: Naka K, Ishihara K, Jomen Y, Jin CH, Kim DH, Gu YK, Jeong ES, Li S, Krause DS, Kim DW, Bae E, Takihara Y, Hirao A, Oshima H, Oshima M, Ooshima A, Sheen YY, Kim SJ, Kim DK. Novel oral transforming growth factor-β signaling inhibitor EW-7197 eradicates CML-initiating cells. Cancer Sci. 2016 Feb;107(2):140-8. doi: 10.1111/cas.12849. PubMed PMID: 26583567; PubMed Central PMCID: PMC4768399.
3: Park SA, Kim MJ, Park SY, Kim JS, Lim W, Nam JS, Yhong Sheen Y. TIMP-1 mediates TGF-β-dependent crosstalk between hepatic stellate and cancer cells via FAK signaling. Sci Rep. 2015 Nov 9;5:16492. doi: 10.1038/srep16492. PubMed PMID: 26549110; PubMed Central PMCID: PMC4637930.
4: Krishnaiah M, Jin CH, Sheen YY, Kim DK. Synthesis and biological evaluation of 5-(fluoro-substituted-6-methylpyridin-2-yl)-4-([1,2,4]triazolo[1,5-a]pyridin-6-yl )imidazoles as inhibitors of transforming growth factor-β type I receptor kinase. Bioorg Med Chem Lett. 2015 Nov 15;25(22):5228-31. doi: 10.1016/j.bmcl.2015.09.058. PubMed PMID: 26483198.
5: Park SY, Kim MJ, Park SA, Kim JS, Min KN, Kim DK, Lim W, Nam JS, Sheen YY. Combinatorial TGF-β attenuation with paclitaxel inhibits the epithelial-to-mesenchymal transition and breast cancer stem-like cells. Oncotarget. 2015 Nov 10;6(35):37526-43. doi: 10.18632/oncotarget.6063. PubMed PMID: 26462028; PubMed Central PMCID: PMC4741946.
6: Park SA, Kim MJ, Park SY, Kim JS, Lee SJ, Woo HA, Kim DK, Nam JS, Sheen YY. EW-7197 inhibits hepatic, renal, and pulmonary fibrosis by blocking TGF-β/Smad and ROS signaling. Cell Mol Life Sci. 2015 May;72(10):2023-39. doi: 10.1007/s00018-014-1798-6. PubMed PMID: 25487606.
7: Son JY, Park SY, Kim SJ, Lee SJ, Park SA, Kim MJ, Kim SW, Kim DK, Nam JS, Sheen YY. EW-7197, a novel ALK-5 kinase inhibitor, potently inhibits breast to lung metastasis. Mol Cancer Ther. 2014 Jul;13(7):1704-16. doi: 10.1158/1535-7163.MCT-13-0903. PubMed PMID: 24817629.
8: Jin CH, Krishnaiah M, Sreenu D, Subrahmanyam VB, Rao KS, Lee HJ, Park SJ, Park HJ, Lee K, Sheen YY, Kim DK. Discovery of N-((4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-5-(6-methylpyridin-2-yl)-1H-imidazol-2 -yl)methyl)-2-fluoroaniline (EW-7197): a highly potent, selective, and orally bioavailable inhibitor of TGF-β type I receptor kinase as cancer immunotherapeutic/antifibrotic agent. J Med Chem. 2014 May 22;57(10):4213-38. doi: 10.1021/jm500115w. PubMed PMID: 24786585.
9: Sheen YY, Kim MJ, Park SA, Park SY, Nam JS. Targeting the Transforming Growth Factor-β Signaling in Cancer Therapy. Biomol Ther (Seoul). 2013 Sep 30;21(5):323-31. doi: 10.4062/biomolther.2013.072. Review. PubMed PMID: 24244818; PubMed Central PMCID: PMC3825194.
10: Yoon JH, Jung SM, Park SH, Kato M, Yamashita T, Lee IK, Sudo K, Nakae S, Han JS, Kim OH, Oh BC, Sumida T, Kuroda M, Ju JH, Jung KC, Park SH, Kim DK, Mamura M. Activin receptor-like kinase5 inhibition suppresses mouse melanoma by ubiquitin degradation of Smad4, thereby derepressing eomesodermin in cytotoxic T lymphocytes. EMBO Mol Med. 2013 Nov;5(11):1720-39. doi: 10.1002/emmm.201302524. Erratum in: EMBO Mol Med. 2014 May;6(5):703. PubMed PMID: 24127404; PubMed Central PMCID: PMC3840488.
