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Carbamide compound and its medicinal usage

A technology of compounds and medicinal salts, applied in organic chemistry, drug combination, cardiovascular system diseases, etc., can solve problems such as low selectivity and targeting

Active Publication Date: 2014-07-02
GENERAL HOSPITAL OF PLA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, the types and quantities of drugs for anti-apoptosis and cell protection available for clinical application are still very small, and their selectivity and targeting are not high. Cellular drugs, especially those with a new mechanism of action, are of great significance

Method used

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  • Carbamide compound and its medicinal usage
  • Carbamide compound and its medicinal usage
  • Carbamide compound and its medicinal usage

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Example 1 (2E)-3-Phenyl-N-[1-(8-quinolylamino)oxocarboxamido-2,2,2-trichloroethyl]-2-acrylamide

[0057]

[0058] Dissolve 6.50 g of cinnamic amide and 8.01 g of chloral hydrate in 300 ml of toluene, and reflux at 110°C for 8 hours to prepare intermediate (2E)-3-phenyl-N-[1-hydroxyl-2,2, 2-Trichloroethyl]-2-acrylamide, dissolve 4.00g of (2E)-3-phenyl-N-[1-hydroxyl-2,2,2-trichloroethyl]-2-acrylamide in In 40ml of anhydrous THF, add 4.9ml of SOCl dropwise at room temperature 2 , After dropping, heated to reflux at 60°C for 3 hours. Evaporate the solvent to dryness, dissolve in 20ml of anhydrous ether, drop into 20ml of concentrated ammonia water at 0°C, and stir for 30min. The layers were separated and evaporated to dryness to obtain 2.93 g of the intermediate (2E)-3-phenyl-N-[1-amino-2,2,2-trichloroethyl]-2-acrylamide. Dissolve 0.58g of 8-aminoquinoline in 8ml of anhydrous THF, add 1ml of DIEA, cool to -10°C, drop in 0.56ml of trichloroethyl chloroformate, and rea...

Embodiment 2

[0059] Example 2 (2E)-3-Phenyl-N-[1-(4-methylphenylamino)oxocarboxamido-2,2,2-trichloroethyl]-2-acrylamide

[0060]

[0061] Using the method of Example 1, the 8-aminoquinoline was changed to p-methylaniline to obtain 0.17 g of white solid. 1 H-NMR (400MHz, DMSO-d 6 )δ2.22(s, 3H); δ6.62-6.67(t, 1H); δ6.91-6.95(d, 1H); δ7.04-7.06(d, 2H); δ7.30-7.33(d , 2H); δ7.40-7.61 (m, 7H); δ9.18-9.20 (d, 1H); δ9.59 (s, 1H). MS (TOF) 448.0 (M+).

Embodiment 3

[0062] Example 3 Compound protection cardiomyocyte activity experiment

[0063] Cardiomyocyte primary culture

[0064] Cardiomyocytes were isolated and cultured according to the method of differential adhesion separation (Kreider, A.Messing, H.Doan, S.U.Kim, R.P.Lisak and D.E.Pleasure, Enrichment of Schwann cell cultures from neonatal rat sciaticnerve by differential adhesion, Brain Res 2 (1981), pp.433444.), took newborn Wistar suckling mice within 24 hours, disinfected the skin of the chest and abdomen with iodine alcohol, used scissors to open the chest slightly to the left of the midline under the xiphoid process, obliquely opened the chest, took out the heart and placed it on ice. Pre-cooled PBS; use 0.01M PBS to gently pipette the heart to remove blood cells and other tissues, and cut the heart into 0.5mm 3 For fragments of different sizes, wash repeatedly 2-3 times with 0.01M PBS; place the fragments in an Erlenmeyer flask, add 4ml 0.125% trypsin, 1ml 0.1% collagen...

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Abstract

The invention relates to a compound as shown in the general formula I, or its isomer, medicinal salt and solvate; the invention also relates to a composition containing the compound as shown in the general formula I or its isomer, medicinal salt and solvate as well as a pharmaceutically acceptable carrier, excipient or diluent; the invention also relates to the usage of the compound as shown in the general formula I, or its isomer, medicinal salt and solvate in resisting cell apoptosis and preventing or treating diseases or symptoms related with cell apoptosis, especially to the usage in protecting cardiomyocytes and preventing or treating diseases or symptoms related with cardiomyocyte apoptosis.

Description

technical field [0001] The present invention relates to the field of medicinal chemistry, specifically, the present invention relates to urea compounds and pharmaceutical compositions thereof, and the present invention also relates to said compounds and pharmaceutical compositions thereof being used for anti-apoptosis, preventing or treating diseases related to apoptosis Use for diseases or symptoms, especially for protecting cardiomyocytes and preventing or treating diseases or symptoms related to cardiomyocyte apoptosis. Background technique [0002] Apoptosis generally refers to a kind of programmed cell death that occurs during the development of cells in the body or under the action of certain factors through the regulation of intracellular genes and their products. Apoptosis is ubiquitous in the biological world, and occurs in both physiological and pathological conditions. It plays an important role in embryonic development and morphogenesis, the stability of normal ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/40C07C275/28A61P9/00A61K31/17A61K31/4706
Inventor 何昆仑李松钟武刘涓王莉莉李鑫胡国梁龙隆肖军海郑志兵李薇李蕊君刘春蕾
Owner GENERAL HOSPITAL OF PLA
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