Compound with functions of anti-fibrosis and inhibition of gelatingase activity and use thereof

A compound and gelatinase technology, applied to the active ingredients of heterocyclic compounds, digestive system, drug combination, etc.

Active Publication Date: 2009-06-10
凯熙医药(天津)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no report about the anti-fibrosis of these compounds or the related application of inhibiting the activity of gelatinase-2 (MMP-2) and gelatinase-9 (MMP-9)

Method used

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  • Compound with functions of anti-fibrosis and inhibition of gelatingase activity and use thereof
  • Compound with functions of anti-fibrosis and inhibition of gelatingase activity and use thereof
  • Compound with functions of anti-fibrosis and inhibition of gelatingase activity and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 11

[0028] [Example 1] 1, the preparation of 2-[two (1,2-benzisoselenazol-3 (2H)-ketone)] ethane

[0029] 1. Preparation of 2-benzoic acid diazonium chloride

[0030] Under ice bath conditions, accurately weigh 14.0g of anthranilic acid, mix it with 40ml of hydrochloric acid with a concentration of 1:1 under ice bath conditions, then slowly drop 9.0g of sodium nitrite into 20ml The water solution was continued to react for 2 hours after dripping to obtain 2-benzoic acid diazonium chloride for later use.

[0031] 2. Preparation of sodium diselenide

[0032] Add 8.8 g of selenium powder and 4.4 g of sodium hydroxide into 60 ml of deionized water, slowly add 8.8 g of sodium thiosulfate under stirring conditions, and continue to react for 2-4 hours to obtain a sodium diselenide solution for later use.

[0033] 3. Preparation of 2,2'-diselenide bisbenzoic acid

[0034] Under the condition of stirring, the chlorinated 2-benzoic acid diazonium salt solution obtained in step 1 was adde...

Embodiment 2

[0040] [Example 2] 1, the preparation of 3-[two (1,2-benzisoselenazol-3 (2H)-ketone)] propane

[0041] Under the conditions of ice bath and nitrogen protection, 0.82ml 1,3-propanediamine was dissolved in 4.5ml of THF, then 6.45ml triethylamine was added, and 5g of 2-selenochlorobenzoyl chloride was slowly added dropwise to dissolve in In the solution of 60ml THHF, it can be seen that a light yellow solid is continuously formed, and after the dropwise addition, it is raised to room temperature and continues to react for 3 hours. After the reaction, the pale yellow precipitate was filtered out, washed several times with tetrahydrofuran, then washed several times with a large amount of water, and finally washed several times with ethanol and ether, the solid was recrystallized with DMSO-water, and dried to obtain 2.52 g of the product. Yield 58.6%, m.p. 254-257°C. 1 H-NMR (300MHz, DMSO-d 6 )7.39-8.05 (m, 4H, ph-H), 3.78 (t, 2H, CH 2 ), 2.00 (dd, J 1 =6.6,J 2 =6.9,2H,CH 2 ...

Embodiment 3

[0042] [Example 3] 1, the preparation of 4-[bis(1,2-benzisoselenazol-3(2H)-one)] butane (hereinafter referred to as ES-03)

[0043] Under the conditions of ice bath and nitrogen protection, dissolve 0.866ml of 1,4-butanediamine in 50mlTHF, add 5.74ml of triethylamine, and slowly add 4.39g of 2-selenochlorobenzoyl chloride dissolved in 60mlTHF solution, a yellow solid was formed. After the dropwise addition, it was raised to room temperature and continued to react for 3 hours. After the reaction, the pale yellow precipitate was filtered out, washed several times with tetrahydrofuran, then washed several times with a large amount of water, and finally washed several times with ethanol and ether, the solid was recrystallized with DMSO-water, and dried to obtain 2.54 g of the product. Yield 65.7%, m.p.243-248°C

[0044] 1 H-NMR: (300MHz, DMSO-d 6 )δ 7.37-8.04(m, 4H, Hh-H), 3.75(s, 2H, CH 2 ), 1.64 (s, 2H, CH 2 ); elemental analysis C 18 h 16 N 2 o 2 Se 2 Calculated (%):...

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Abstract

The invention discloses a groups of compounds with functions of anti-fibrosis and inhibition of gelatingase activity and their use, test results show that, the compounds can effectively inhibit the activity of gelatinase-2 (MMP-2) and gelatinase-9 (MMP-9), thus can be used for preparing medicament for preventing or treating fibrosis diseases, periodontitis, arthritis, combination fibrosis, tumor metastasis and related diseases.

Description

technical field [0001] The present invention relates to oxazolone compounds and their applications, and methods for synthesizing such compounds, in particular to bisbenzisoselenazolones and their use in the preparation of gelatinase-2 (MMP-2) or gelatinase-9 (MMP-9) activity-related disease drug application. Background technique [0002] Selenium is one of the important trace elements. The blood selenium content in the human body is lower than 0.1ppm for a long time, which may cause many diseases such as liver necrosis, myocardial injury, cancer and arthritis. The importance of selenium to life sciences has made selenium-containing medicines or their health products the focus of attention. Generally, inorganic selenium is not easily absorbed, has low biological activity and high toxicity. Organic selenium is easily absorbed by the body, maintains in the blood for a long time, is easily converted into active intermediates in the body, and has long biological activity and re...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D293/12A61P1/16A61P35/00A61P17/16A61P43/00A61K31/41A61K9/00A61K8/49
Inventor 曾慧慧
Owner 凯熙医药(天津)有限公司
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