Oxygen-containing heterocyclic substituted azole compound and applications thereof

A compound, C1-C3 technology, applied in the field of medicinal chemistry, can solve problems such as 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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  • Oxygen-containing heterocyclic substituted azole compound and applications thereof
  • Oxygen-containing heterocyclic substituted azole compound and applications thereof
  • Oxygen-containing heterocyclic substituted azole compound and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0178] N-(3-(Benzo[d][1,3]dioxol-5-yl)-1H-pyrazol-5-yl)-4-((1-methylpiperidine-4 -yl)amino)benzamide (1)

[0179] Into a round-bottomed flask were added sequentially tetrahydrofuran (12ml), acetonitrile (5mL), sodium hydride (0.17g, 7.1mmol) and benzo[d][1,3]dioxole-5 under ice-bath conditions. -Methyl formate (0.43g, 2.4mmol), stirred for 0.5h and then heated to reflux, reacted for 5h. The reaction solution was poured into ice-water mixture (30ml), and the pH was adjusted to 2. A large amount of yellow solid precipitated, which was filtered and dried to obtain a crude product. After the crude product was subjected to column chromatography (PE:EA=2:1), 0.413 g of a light yellow solid was obtained, with a yield of 91%. MS[M-H] + 188.03.

[0180] The product obtained in the previous step, hydrazine hydrochloride (0.45g, 4.4mmol), triethylamine (0.44g, 4.4mmol) and ethanol (10ml) were sequentially added into a 25mL round bottom flask, and refluxed for 8h. The reaction soluti...

Embodiment 2

[0183] N-(3-(Benzo[d][1,3]dioxol-5-yl)-1H-pyrazol-5-yl)-4-(4-methylpiperazine-1- base) benzamide (2)

[0184] The preparation method is similar to (1), and a light yellow solid is obtained. 1 H NMR (300MHz, CDCl3) δ12.7 (s, 1H), 10.3 (s, 1H), 7.64-7.57 (m, 2H), 7.35 (d, 1H), 7.22 (d, 1H), 7.06-6.99 ( m, 2H), 6.88-6.81(m, 2H), 6.07(s, 2H), 3.20(t, 4H), 2.98(t, 4H), 2.60(s, 3H). MS(m / z): [ M+H] + 406.2.

Embodiment 3

[0186] N-(3-(Benzo[d][1,3]dioxol-5-yl)-1H-pyrazol-5-yl)-4-(piperidin-1-yl)benzyl Amides (3)

[0187] The preparation method is similar to (1), and a light yellow solid is obtained. 1 H NMR (300MHz, CDCl3) δ12.7(s, 1H), 10.3(s, 1H), 7.59-7.52 (m, 2H), 7.25(d, 1H), 7.19(d, 1H), 7.01(d, 1H), 6.89-6.82(m, 2H), 6.52(s, 1H), 6.07(s, 2H), 3.49-3.43(m, 4H), 1.67-1.57(m, 6H).MS(m / z) : [M+H] + 391.2.

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Abstract

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

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to oxygen-containing heterocyclic substituted azole compounds, their preparation methods, pharmaceutical compositions containing these compounds and their medical applications. Background technique [0002] Cell signal transduction plays a key role in regulating cell growth, proliferation, differentiation, apoptosis and other processes. The imbalance of cell proliferation and apoptosis leads to major diseases such as cancer, and the essence of cell canceration is the imbalance of cell signal transduction. When the cell signal transduction pathway that regulates the normal physiological activities of cells is changed under the action of carcinogens, the normal biological effects of regulating cell growth, division and differentiation will be abnormal, which will cause abnormal cell growth, division and cell morphology. changes that lead to cancer. Since it plays a key role in cel...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/14C07D491/113A61K31/496A61K31/454A61K31/5377A61K31/519A61P35/00
CPCC07D405/14C07D491/113A61P35/00
Inventor 卢帅王志杰向黎王淑贤衡浩蔡炅桁秦天人田洁怡陈亚东陆涛
Owner CHINA PHARM UNIV
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