Anti-inflammatory compound having inhibitory activity against multiple tyrosine kinases, and pharmaceutical composition containing same

A compound and pharmaceutical technology, applied in the field of anti-inflammatory compounds with various tyrosine kinase inhibitory activities and pharmaceutical compositions containing these compounds

Active Publication Date: 2013-03-13
PHAROSBIOMED CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, their overexpression, overactivation or decreased activity are directl

Method used

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  • Anti-inflammatory compound having inhibitory activity against multiple tyrosine kinases, and pharmaceutical composition containing same
  • Anti-inflammatory compound having inhibitory activity against multiple tyrosine kinases, and pharmaceutical composition containing same
  • Anti-inflammatory compound having inhibitory activity against multiple tyrosine kinases, and pharmaceutical composition containing same

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0214]

preparation example 1-1

[0216] Synthesis of 1-(4-(methoxy-benzyloxy)-3-nitrobenzene

[0217] Add sodium hydroxide (0.54 g, 13.36 mmol) to 10 ml of degassed dimethylformamide at 0 °C, and then slowly dropwise add 3-nitrophenol (1.69 g, 12.14 mmol) dissolved in 7 ml of di Methylformamide, then p-methoxybenzyl chloride (1.81ml, 13.36mmol) was added slowly. After raising the reaction temperature to room temperature and stirring for 2 hours, the reaction mixture was extracted with saturated ammonium chloride (100 ml) and ethyl acetate (100 ml). The organic layer was washed twice with 100 ml of water, dried over anhydrous sodium sulfate, and then concentrated under vacuum. Recrystallization from n-hexane finally gave 1-(4-methoxybenzyloxy)-3-nitrobenzene (2.85 g, 90%) as a pale yellow solid.

[0218] 1 H-NMR(600MHz, CDCl3);δ7.83-7.81(m,2H),7.42(t,J=8.4Hz,1H),7.37(d,J=8.4Hz,2H),7.28(dd,J, 2.4,8.4Hz,1H),6.93(d,J=8.4Hz,2H),5.06(s,2H),3.82(s,3H)

preparation example 1-2

[0220] Synthesis of 3-(4-methoxybenzyloxy)aniline

[0221] Iron (5.6 g, 100.28 mmol) was mixed with methanol:water (15 ml:3 ml) and refluxed for 30 minutes. When the temperature dropped to room temperature, 1-(4-methoxybenzyloxy)-3-nitrobenzene (1.3 g, 5.01 mmol) was dissolved in 6 mL of methanol:water (5:1) solution, and after adding Reflux for 15 hours. Fe was removed with cellite, then the reaction mixture was washed with methanol and concentrated under vacuum to remove solvent. After extraction with 100 ml of saturated ammonium chloride + 150 ml of dichloromethane, the organic layer was washed with water. The organic solvent was concentrated in vacuo to give the title compound (1.14 g, 99%).

[0222] 1 H-NMR (400MHz, CDCl3); 6.31(m,3H),4.94(s,2H),3.81(s,3H)

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PUM

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Abstract

The present invention relates to an anti-inflammatory compound having inhibitory activity against tyrosine kinases, and a pharmaceutical composition containing the same as an active ingredient. The compound according to the present invention can inhibit the activity of multiple tyrosine kinases, and thus can be used for efficiently preventing or treating inflammatory diseases, autoimmune diseases or the like related to the tyrosine kinases.

Description

technical field [0001] The present invention describes a series of compounds with hydroxy (or methyl) anilinothienopyrimidine and hydroxy (or methyl) anilinothienopyridinidine as common pharmacophore, and having various tyrosine kinase inhibitory activities And the pharmaceutical compositions with these compounds as active ingredients. The above pharmaceutical composition can be used to prevent or treat various inflammatory diseases and immune disorders, and can also be used to promote wound repair and inhibit scar formation. Background technique [0002] The inflammatory response is mainly due to the activation of inflammatory immune cells. In various inflammatory diseases, it is often found that activated inflammatory immune cells affect adjacent fibroblasts, epithelial cells or smooth muscle cells and are activated into myoblasts. When fibroblasts, epidermal cells or smooth muscle cells are activated Activation into myoblasts exhibits increased proliferation and migrati...

Claims

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Application Information

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IPC IPC(8): C07D495/04C07D495/02A61K31/519A61K31/4743A61K9/70A61K9/06A61P29/00
CPCC07D495/04A61P1/04A61P1/16A61P7/00A61P7/06A61P9/10A61P11/00A61P11/02A61P11/06A61P13/12A61P17/02A61P17/04A61P17/06A61P19/02A61P19/06A61P21/04A61P25/00A61P27/02A61P27/14A61P29/00A61P31/04A61P37/00A61P37/06A61P37/08A61P43/00A61K31/519
Inventor 梁范锡金容柱朴泰教禹成昊李享俶金璇暎赵钟云李洪凡
Owner PHAROSBIOMED CO LTD
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