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Aminothiazole compounds and use thereof

A compound and amino technology, applied in the field of aminothiazole compounds and their uses, can solve the problems of poor kinase selectivity, animal death and the like

Active Publication Date: 2018-12-21
台湾卫生研究院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Furthermore, aminothiazoles have poor kinase selectivity as promiscuous protein kinase inhibitors
Furthermore, in toxicity studies, they frequently cause animal deaths, which raises safety concerns

Method used

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  • Aminothiazole compounds and use thereof
  • Aminothiazole compounds and use thereof
  • Aminothiazole compounds and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Embodiment 1: the synthesis of compound 1

[0054] Compound 1 was prepared according to the synthetic method described in Chen et al., European Journal of Medicinal Chemistry, 2015, 100, 151-161.

[0055] All chemicals and solvents were purchased from commercial suppliers and used as received. All reactions were performed under dry nitrogen atmosphere. The reaction was monitored by TLC using a Merck 60 F254 silica gel glass backplate (5×10 em); and each was detected visually under UV light irradiation (254 nm) or by spraying phosphomolybdic acid reagent (Aldrich) followed by heating at 80° C. area. All flash column chromatography was performed using Merck Kieselgel 60, No. 9385, 230-400 mesh ASTM silica gel as stationary phase. Proton ( 1 H) The nuclear magnetic resonance spectrum is measured with a Varian Mercury-300 or Varian Mercury-400 spectrometer. Chemical shifts are reported in parts per million (ppm) on a scale relative to the delta of the solvent peak reso...

Embodiment 2

[0061] 1-(5-Ethyl iso Azol-3-yl)-3-(4-(2-((6-(4-ethylpiperazin-1-yl)pyrimidin-4-yl)amino)thiazol-5-yl)phenyl)urea ( Hydrochloride)

[0062]

[0063] 1 H NMR (400MHz, DMSO-d6): δ11.14(s, 1H), 9.78(s, 1H), 9.62(s, 1H), 8.48(s, 1H), 7.74(s, 1H), 7.50(q , J=8.8Hz, 4H), 6.55(s, 1H), 6.38(s, 1H), 4.34(d, J=14.0Hz, 2H), 3.55(d, J=11.6Hz, 2H), 3.44-3.38 (m, 2H), 3.14-3.08(m, 2H), 3.00(q, J=9.6Hz, 2H), 2.69(q, J=7.6Hz, 2H), 1.26(t, J=7.6Hz, 3H) , 1.19(t, J=7.6Hz, 3H); MS(ES + )m / z(C 25 h 29 N 9 o 2 S) Calculated value: 519.22; Actual value: 520.2 (M+H + ).

Embodiment 3

[0065] 1-(5-Ethyl iso Azol-3-yl)-3-(4-(2-((6-(2-morpholineethoxy)pyrimidin-4-yl)amino)thiazol-5-yl)phenyl)urea (hydrochloride )

[0066]

[0067] 1 H NMR (400MHz, DMSO-d6): δ11.08(s, 1H), 9.75(s, 1H), 9.56(s, 1H), 8.62(s, 1H), 7.73(s, 1H), 7.50(q , J=8.8Hz, 4H), 6.54(s, 1H), 6.50(s, 1H), 4.71(s, 2H), 3.95(d, J=11.6Hz, 2H), 3.79(t, J=12.4Hz , 2H), 3.56(s, 2H), 3.47(d, J=12.4Hz, 2H), 3.15(d, J=10.0Hz, 2H), 2.69(q, J=7.6Hz, 2H), 1.19(t , J=7.6Hz, 3H); MS(ES + )m / z(C 25 h 28 N 8 o 4 S) Calculated value: 536.20; Actual value: 537.2 (M+H + ).

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Abstract

Aminothiazole compounds of Formula (I) shown herein and pharmaceutical compositions containing one of such compounds. Also disclosed are methods, each of which uses one of the aminothiazole compoundsto inhibit a protein kinase or to treat cancer associated with a protein kinase.

Description

Background technique [0001] Protein kinases are important in cell signaling pathways that regulate various cellular functions including differentiation, proliferation, migration, and apoptosis. Deregulation of protein kinases is implicated in cancer and many other diseases. [0002] Heterocyclic compounds have been extensively studied as potent protein kinase inhibitors. Among various classes of heterocyclic compounds, aminothiazoles exist as repeating structural motifs in many biologically active compounds. [0003] Aminothiazoles present several challenges as drug candidates. First, they often lack sufficient in vivo exposure to exert the desired efficacy in preclinical or clinical studies. Furthermore, aminothiazoles have poor kinase selectivity as promiscuous protein kinase inhibitors. Furthermore, they frequently cause animal death in toxicity studies, which raises safety concerns. [0004] It is necessary to develop new aminothiazoles that effectively inhibit specif...

Claims

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Application Information

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IPC IPC(8): A61K31/496A61K31/5377C07D403/12
CPCA61P35/00C07D417/14A61K31/496A61K31/5377
Inventor 姜韦汤许楚
Owner 台湾卫生研究院
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