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Novel fused imidazole derivative

一种化合物、杂环基的技术，应用在新稠环咪唑衍生物领域，能够解决没有报道稠环咪唑衍生物等问题

Inactive Publication Date: 2008-01-02
MSDK K
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, no fused-ring imidazole derivatives with excellent PLK1 inhibitory effects have been reported so far

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0461] Synthesis of 3-(benzyloxy)-5-imidazo[1,2-a]pyridin-3-yl-2-thiophenecarboxylic acid [1] (hereinafter referred to as compound [1])

[0462] (1) 10.0 g of imidazo[1,2-a]pyridine was dissolved in 80 ml of acetonitrile, and 19.0 g of N-iodosuccinimide was added at room temperature. After stirring at room temperature for 2 hours, the precipitated powder was collected by filtration and washed with ether to obtain 3-iodoimidazo[1,2-a]pyridine[1-1] (hereinafter referred to as compound [1-1] in the form of light yellow solid. -1]) 17.2g.

[0463](2) Dissolve 3.66g of compound [1-1] in 80ml of tetrahydrofuran, add 4.15g of potassium carbonate, 1.05g of bis(triphenylphosphine)palladium(II) dichloride, 571mg of copper iodide, methacrylic acid 2.67ml of alkynoic acid was stirred at 60°C for 4 hours in a nitrogen atmosphere. The insoluble matter was filtered with celite, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column...

Embodiment 2

[0470] 5-imidazo[1,2-a]pyridin-3-yl-3-{[2-(trifluoromethyl)benzyl]oxy}thiophene-2-carboxylic acid [2] (hereinafter referred to as compound [2] )Synthesis

[0471] The target compound [2] was obtained as a colorless oily substance from compound [1-3] and 2-trifluoromethyl-benzyl alcohol according to the method of Example 1-(4) to (5).

[0472] The target compound was identified by LC-MS.

[0473] Mass spectrum: 419 (M+1) + .

Embodiment 3

[0475] Synthesis of 3-[(2-chlorobenzyl)oxy]-5-imidazo[1,2-a]pyridin-3-ylthiophene-2-carboxylic acid [3] (hereinafter referred to as compound [3])

[0476] The trifluoroacetate of the target compound [3] was obtained as a colorless oily substance from the compound [1-3] and m-chlorobenzyl alcohol according to the method of Example 1-(4)-(5).

[0477] The spectral data of compound [3] are shown below.

[0478] 1 H-NMR (DMSO-d 6 )δ: 8.94(d, J=7.0Hz, 1H), 8.39(s, 1H), 7.94(d, J=9.0Hz, 1H), 7.79-7.75(m, 3H), 7.56(m, 1H), 7.48-7.39(m, 3H), 5.46(s, 2H).

[0479] Mass spectrum: 385, 387 (M+1) +

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Abstract

Disclosed is a compound represented by the general formula [I] below or a pharmaceutically acceptable salt or ester thereof. [I] [In the formula, the ring A represents a five-membered aromatic heterocyclic group containing at least one heteroatom selected from a nitrogen atom or the like; A1 and A2 represent nitrogen atoms or the like; all of X2, X3, X4 and X5 represent carbon atoms, or one of X2, X3, X4 and X5 represents a nitrogen atom and the rest represent carbon atoms; R1 represents a hydrogen atom or the like; R2, R3, R4 and R5 represent hydrogen atoms or the like; R6 and R6' represent hydrogen atoms or the like; R7 represents an aryl group or the like; and R8 represents an amino group or a hydroxy group.

Description

technical field [0001] The present invention relates to a new fused-ring imidazole derivative, a PLK1 inhibitor containing the same and an anticancer agent. The new fused-ring imidazole derivative can be used in the field of medicine, and it inhibits the proliferation of tumor cells based on the PLK1 inhibitory effect and exerts an anti-tumor effect. Background technique [0002] It is generally believed that compared with normal cells, cancer cells generally proliferate more actively. In most cases, the cause of cancer is the disordered proliferation caused by the abnormality of the cell cycle control mechanism. In the cell cycle, the mitotic phase (M phase) is a step in which chromosomes are equally distributed to daughter cells, and strict control of this process is essential for cell proliferation and survival. Therefore, it is believed that inhibiting the progress of M phase is an effective means to inhibit cell proliferation. In fact, anticancer agents targeting M phas...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A61K31/437A61K31/444A61K31/4545A61K31/497A61K31/4985A61K31/5025A61K31/5377A61P35/00A61P43/00C07D487/04
CPCC07D471/04C07D487/04A61P35/00A61P43/00
Inventor 佐藤祯之栗原秀树上条香织小野崎祐辻野俊明杉本哲哉渡边明子三谷守宏驹谷秀也
Owner MSDK K
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