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2-aminothiazoles compound

A compound, alkyl technology, applied in the field of application in the preparation of drugs, can solve problems such as drug resistance

Active Publication Date: 2013-06-05
CHIA TAI TIANQING PHARMA GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, continuous imatinib therapy is highly prone to drug resistance, and some CML patients relapse in advanced or explosive crisis stages

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0139] Example 1: N-{4-[(4-methylpiperazinyl)methyl]phenyl}-4-methyl-3-[4-(pyridin-3-yl)thiazole-2-amino]benzene Preparation of formamide (reference)

[0140]

[0141] Step A: Preparation of methyl 3-(3-acetylthiourea)-4-methylbenzoate

[0142]

[0143] Ammonium thiocyanate (50 mmol) was dissolved in 50 ml of acetone, a solution of acetyl chloride (50 mmol) in 10 ml of acetone was added dropwise at 40°C, stirred for 1 hour, then cooled to room temperature, and 3-amino-4 - 75 ml of acetone solution of methyl methylbenzoate, stirred at room temperature for 5 hours, added 100 ml of water, continued to stir for 1 hour, filtered the precipitate, washed 3 times with water and 3 times with n-hexane, and dried in vacuo to obtain the title compound 11.3 grams. 1 H-NMR (DMSO), δ12.19(1H, s), 11.56(1H, s), 8.18(1H, s), 7.77(1H, d, J=8.0Hz), 7.45(1H, d, J= 8.0Hz), 3.84(3H, s), 2.27(3H, s), 2.17(3H, s).

[0144] Step B: Preparation of methyl 4-methyl-3-[4-(pyridin-3-yl)thiazole-2...

Embodiment 2

[0153] Example 2: N-{3-trifluoromethyl-4-[(4-methylpiperazinyl)methyl]phenyl}-4-methyl-3-[4-(pyridin-3-yl) Preparation of Thiazole-2-amino]benzamide

[0154]

[0155] According to the synthesis method in Step D of Example 1, the compound in Step C of Example 1 was reacted with 4-[(4-methylpiperazinyl)methyl]-3-trifluoromethylaniline to obtain 20 mg of the title compound. 1 H-NMR (CDCl 3), δ9.61(1H, s), 9.12(1H, s), 8.83(1H, s), 8.49(1H, s), 8.23(1H, d, J=6.8Hz), 7.58(1H, d, J=7.2Hz), 7.51(1H, s), 7.42(1H, s), 7.32(1H, d, J=7.2Hz), 2.36(3H, s).MS: m / z, 567.2(M+H ).

Embodiment 3

[0156] Example 3: N-{4-methyl-3-[4-(6-trifluoromethyl-imidazo[1,2-a]pyridin-3-yl)thiazole-2-amino]phenyl}-3 -Preparation of trifluoromethyl-4-[(4-methylpiperazinyl)methyl]benzamide

[0157]

[0158] Step A: (E)-N,N-Dimethyl-N'-[5-(trifluoromethyl)pyridin-2-yl]formamidine

[0159]

[0160] 5-Trifluoromethyl-2-aminopyridine (20.1 mmol) was dissolved in 10 ml of N,N-dimethylformamide dimethyl acetal, and heated to reflux at 110° C. for 1 hour. The solvent was removed by concentration to obtain 4.2 g of the title compound. 1 H-NMR (CDCl 3 )δ8.52(1H, s), 8.47(1H, s), 7.73(1H, d, J=8Hz), 6.99(1H, d, J=8Hz), 3.14(6H, d, J=8Hz).

[0161] Step B: Preparation of 1-[6-trifluoromethyl-imidazo[1,2-a]pyridin-3-yl]ethanone

[0162]

[0163] The above compound (1 g, 4.6 mmol), sodium iodide (4.4 mmol) and bromoacetone (8.28 mmol) were dissolved in dry N,N-dimethylformamide (5 ml) at 100 Stir at °C for 4 hours. Cool to room temperature, concentrate to remove the solvent, add 20 ...

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PUM

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Abstract

The invention relates to the technical field of medicinal chemistry, in particular to a 2-aminothiazoles compound or acceptable slat in pharmaceutical science, a preparing method thereof, pharmaceutical composition comprising the same, and application thereof in antineoplastic drug preparation.

Description

technical field [0001] The present invention relates to the technical field of medicinal chemistry, in particular to a class of 2-aminothiazole compounds with a new structure or pharmaceutically acceptable salts thereof, pharmaceutical compositions containing such compounds and their application in the preparation of medicines. Background technique [0002] Malignant tumor is currently the number one killer of human health, and its incidence rate is second only to cardiovascular diseases. The occurrence and development of tumors are related to the overexpression of cell signals. Protein kinases, as important mediators of signal transduction, have received widespread attention. Among them, tyrosine kinases are the most extensive and important kinase family in the human body, and have become important targets in tumor research. . In recent years, although some new tyrosine protein kinase inhibitors have been developed and marketed, they are still far from meeting the growing ...

Claims

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Application Information

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IPC IPC(8): C07D417/04C07D471/04C07D487/04C07D277/46C07D277/42C07D498/04C07D417/14A61K31/496A61K31/506A61K31/5025A61K31/5383A61P35/02A61P35/00
Inventor 校登明梁志胡远东胡全张庆辉韩永信王欢彭勇孔凡胜罗鸿
Owner CHIA TAI TIANQING PHARMA GRP CO LTD
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