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Epoxidase-2 selective inhibitor as well as preparation method and application thereof

A cyclooxygenase and selective technology, applied in the field of medicine, can solve the problems of inappropriate COX-2/COX-1 selectivity, side effects, and limited COX-2 inhibitors, and achieve cheap and easy-to-obtain raw materials and synthetic routes Effects of Short, Significant Selective Inhibition

Inactive Publication Date: 2015-06-10
GUANGZHOU YINGYU PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, the problem in this field is that the selectivity for COX-2 / COX-1 is not suitable. No selectivity and too high selectivity will cause certain side effects. COX-2 inhibitors with moderate selectivity will have good Clinical use effect, the COX-2 inhibitors currently available for clinical selection are still very limited

Method used

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  • Epoxidase-2 selective inhibitor as well as preparation method and application thereof
  • Epoxidase-2 selective inhibitor as well as preparation method and application thereof
  • Epoxidase-2 selective inhibitor as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1 (compound 1)

[0035] The preparation method of 4-[3,5-bis(2-hydroxyphenyl)-1-(1,2,4-triazolyl)]benzenesulfonamide, the steps comprising:

[0036] (1) Add 40ml of xylene and salicylic acid (17.3g, 120mmol) into a 250ml reaction bottle, slowly add 10ml of thionyl chloride with a dropping funnel, leave it for 30min after the dropwise addition, add salicylamide (11.2g, 80mmol), stirred and reacted at room temperature (20-25°C) for 5h, tracked the reaction by TLC, after the reaction was complete, evaporated the organic solvent under reduced pressure to obtain a yellow viscous solid, added 50ml of ethanol, heated to reflux for 1h, and cooled to room temperature , stood still, and 7.6g of yellow powdery solid compound 1a was precipitated.

[0037] (2) Add compound 1a (0.72g, 3mmol) and p-hydrazinobenzenesulfonamide (0.67g, 3.5mmol) to 25ml of methanol, heat to reflux for 10h, follow the reaction by thin-layer chromatography, and cool to room temperature after the r...

Embodiment 2

[0039] Example 2 (compound 1)

[0040] The preparation method of 4-[3,5-bis(2-hydroxyphenyl)-1-(1,2,4-triazolyl)]benzenesulfonamide, the steps comprising:

[0041] (1) Add salicylamide (11.2g, 80mmol) and 40ml of xylene into a 250ml reaction bottle, heat to dissolve, slowly drop salicyloyl chloride (22.7g, 0.12mol) into the reaction solution, after adding , stirred at room temperature for 5 hours, followed by thin-layer chromatography. After the reaction was complete, the organic solvent was evaporated under reduced pressure to obtain a yellow viscous solid, which was added with 25ml of ethanol, refluxed for 1 hour, cooled to room temperature, left to stand, and yellow needle-shaped crystals were precipitated , the mother liquor was further concentrated and crystallized, and a total of 7.8 g of compound 1a was obtained.

[0042] (2) Add compound 1a (0.72g, 3mmol) and p-hydrazinobenzenesulfonamide (0.67g, 3.5mmol) to 25ml of methanol, heat to reflux for 10h, follow the reactio...

Embodiment 3

[0044] Example 3 (compound 1)

[0045] The preparation method of 4-[3,5-bis(2-hydroxyphenyl)-1-(1,2,4-triazolyl)]benzenesulfonamide, the steps comprising:

[0046] (1) Add 40ml of xylene and salicylic acid (17.3g, 120mmol) into a 250ml reaction bottle, slowly add 10ml of thionyl chloride with a dropping funnel, leave it for 30min after the dropwise addition, add salicylamide (11.2g, 80mmol), reacted at room temperature for 5h, tracked the reaction by thin-layer chromatography, after the reaction was complete, evaporated the organic solvent under reduced pressure to obtain a yellow viscous solid, added 50ml of ethanol, heated to reflux for 1h, cooled to room temperature, stood still, and precipitated 7.6g Yellow powdery solid compound 1a.

[0047] (2) Add compound 1a (0.76g, 3mmol), p-hydrazinobenzenesulfonamide hydrochloride (0.65g, 3.5mmol) into 25ml of methanol, reflux for 12h, cool to room temperature, and then continue to drop to 0-5 ℃ for 1h. The precipitated solid was...

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Abstract

The invention discloses an epoxidase-2 selective inhibitor as well as a preparation method and application thereof. According to the epoxidase-2 selective inhibitor, with substituted benzamide and a substituted benzoic acid derivative as raw materials, a 4-[3,5-bis(substituted-phenyl)-1-(1,2,4-triazole)] benzenesulfonic acid derivative is obtained through condensation reaction and ring closing reaction of a p-hydrazino-benzenesulfonic acid derivative. The epoxidase-2 selective inhibitor has the beneficial effects that the epoxidase-2 selective inhibitor has a significant selective inhibiting effect on epoxidase COX-2 activity, and is capable of obviously inhibiting foot swelling in mice caused by carrageenin; and a target compound is expected to become a medicine for treating inflammation, rheumatoid arthritis, and diseases related to epoxidase-2.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a cyclooxygenase-2 (cyclooxygenase-2 (COX-2)) selective inhibitor and its preparation method and application. Background technique [0002] Cyclooxygenase (COX) is a key enzyme that controls the metabolism of arachnidonic acid (AA) and the biosynthesis of prostaglandin (arachidonic acid, PG). There are two isoenzymes of cyclooxygenase, cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2), and the regulation of the two isoenzymes at the structure and molecular level is different. features. COX-1 exists in a variety of tissues, most of which are stomach, kidney, and platelets. The PG produced by it can protect the normal physiological functions of the organ and is a physiologically active component; COX-2 is induced by inflammatory factors and produced in the inflammatory site PG produced by macrophages, synoviocytes, chondrocytes, endothelial cells, fibroblasts and other cells can cause...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/08A61P29/00A61P19/02A61P43/00
CPCC07D249/08
Inventor 康健
Owner GUANGZHOU YINGYU PHARMA TECH CO LTD
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