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Indole substituted azole compound and applications thereof

A compound, indole technology, applied in the field of medicinal chemistry, can solve the problem of weak selectivity of kinase inhibitors

Active Publication Date: 2020-02-25
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, there is evidence that side effects of kinase inhibitors are related to their poor selectivity

Method used

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  • Indole substituted azole compound and applications thereof
  • Indole substituted azole compound and applications thereof
  • Indole substituted azole compound and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0239] N-(3-(1H-indol-2-yl)-1H-pyrazol-5-yl)-4-(4-methylpiperazin-1-yl)benzamide (1)

[0240] Into a round bottom flask were added sequentially tetrahydrofuran (12ml), acetonitrile (6mL), sodium hydride (0.17g, 7.1mmol) and methyl 1-tert-butoxyformyl-1H-indole-2-carboxylate under ice bath condition (0.688g, 2.5mmol), stirred for 0.5h and then heated to reflux for 6h. The reaction solution was poured into an ice-water mixture (50ml), and a white solid precipitated out, which was filtered and dried to obtain a crude product. After the crude product was subjected to column chromatography (PE:EA=7:1), 0.334 g of a white solid was obtained, with a yield of 47%. MS[M-H] - 283.1.

[0241] Into a 25mL round-bottomed flask, all the products from the previous step, hydrazine hydrochloride (0.231g, 2.2mmol), triethylamine (0.44g, 4.4mmol) and ethanol (10ml) were sequentially added, and the reaction was refluxed for 8h. The reaction solution was diluted with water (50ml), adjusted to ...

Embodiment 2

[0246] N-(3-(1H-indol-2-yl)-1H-pyrazol-5-yl)-4-((1-methylpiperidin-4-yl)amino)benzamide (2)

[0247] The preparation method is similar to (1), and a light yellow solid is obtained. 1 H NMR (300MHz, CDCl 3 )δ12.86(s, 1H), 11.39(s, 1H), 10.32(s, 1H), 7.71(d, 1H), 7.69-7.59(m, 3H), 7.12(t, 1H), 7.06-6.96 (m, 2H), 6.82-6.75(m, 2H), 6.07(s, 1H), 4.35(s, 1H), 3.31-3.2(m, 1H), 2.76-2.74(m, 2H), 2.18(s , 3H), 2.08-2.0(m, 2H), 1.90-1.88(m, 2H), 1.47-1.37(m, 2H). MS(m / z): [M+H] + 415.2.

Embodiment 3

[0249] N-(3-(1H-indol-6-yl)-1H-pyrazol-5-yl)-4-((1-methylpiperidin-4-yl)amino)benzamide (3)

[0250] The preparation method is similar to (1), and a light yellow solid is obtained. 1 H NMR (300MHz, CDCl 3 )δ12.86(s, 1H), 10.47(s, 1H), 10.32(s, 1H), 7.87(dd, 1H), 7.77(d, 1H), 7.66-7.58(m, 3H), 7.18(d , 1H), 6.82-6.75(m, 2H), 6.56(dd, 1H), 6.53(s, 1H), 4.35(s, 1H), 3.31-3.2(m, 1H), 2.76-2.74(m, 2H ), 2.18(s, 3H), 2.08-2.0(m, 2H), 1.90-1.88(m, 2H), 1.47-1.37(m, 2H). MS(m / z): [M+H] + 415.2.

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Abstract

The invention relates to the field of medicinal chemistry, discloses an indole substituted azole compound and applications thereof, and specifically relates to an indole substituted azole compound anda preparation method thereof, a pharmaceutical composition containing the indole substituted azole compound, and medical applications of the indole substituted azole compound and the pharmaceutical composition, especially applications as FMS-like tyrosine kinase 3 inhibitors.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to indole-substituted azole compounds, their preparation methods, pharmaceutical compositions containing these compounds and their medical applications. Background technique [0002] Leukemia is a malignant neoplastic disease of the hematopoietic system, and it is a hematological system tumor in which hematopoietic stem / progenitor cells undergo malignant lesions. Leukemia can be divided into two categories according to the natural course of the disease and the degree of cell proliferation in different stages: acute leukemia and chronic leukemia. According to the different types of proliferating leukemia cells, it can be divided into two categories: acute lymphocytic leukemia (ALL) and acute myelogenous leukemia (AML). Among them, AML accounts for 60%-70% of newly diagnosed acute leukemia in adults, and shows an increasing trend year by year (Environmental Health Perspectives, 200...

Claims

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Application Information

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IPC IPC(8): C07D403/04C07D405/14C07D401/14A61K31/454A61K31/496A61K31/5377A61P35/02A61P35/00
CPCC07D403/04C07D405/14C07D401/14A61P35/02A61P35/00
Inventor 卢帅王志杰衡浩向黎王淑贤蔡炅桁秦天人田洁怡陈亚东陆涛
Owner CHINA PHARM UNIV
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