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Emodin succinyl ester compound and preparation method and use thereof

A technology of emodin succinyl esters and compounds, which is applied in the fields of drug synthesis and medicine and health, can solve the problems of high toxicity and poor absorption, and achieve the effect of low cost, less use, and accelerated skin wound healing

Active Publication Date: 2020-12-22
JIANGSU KANION PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, emodin itself has the disadvantages of high toxicity and poor absorption by the body, and there is no direct clinical report of emodin.

Method used

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  • Emodin succinyl ester compound and preparation method and use thereof
  • Emodin succinyl ester compound and preparation method and use thereof
  • Emodin succinyl ester compound and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050]Example 1 Preparation of emodin succinyl ethyl ester

[0051]Take succinic anhydride (1.0g, 10mmol) in a 10mL round-bottomed flask, use ethanol (3.5mL, 60mmol) as the solvent, heat to reflux for 4 hours, and distill under reduced pressure to remove excess ethanol to obtain a pale yellow oily substance called succinic acid mono Ethyl ester (1.4g, 96%), the product was directly subjected to the next reaction without separation.

[0052]Take monoethyl succinate (1.0g, 6.8mmol) into a 10mL round-bottomed flask, use thionyl chloride (4.0g, 34.0mmol) as the solvent, heat to reflux for 2 hours, and distill under reduced pressure to remove excess thionyl chloride Sulfone, a light yellow oily succinate monoethyl chloride (1.1 g, 98%) was obtained, and the product was directly subjected to the next reaction without separation.

[0053]Take emodin (1.0g, 3.7mmol) and pyridine (0.45g, 5.6mmol) in a 10mL round-bottomed flask, use dichloromethane (3mL) as a solvent, slowly add succinate monoethyl ch...

Embodiment 2

[0057]Example 2 Preparation of emodin succinyl ethyl ester

[0058]Put succinic anhydride (10g, 100mmol) in a 150mL round-bottomed flask, use ethanol (40mL, 600mmol) as the solvent, heat to reflux for 6 hours, and distill under reduced pressure to remove excess ethanol to obtain a pale yellow oily monoethyl succinate (14g, 96%), the product was directly subjected to the next reaction without separation.

[0059]Take monoethyl succinate (10g, 68mmol) and place it in a 150mL round-bottomed flask. Use thionyl chloride (40g, 340mmol) as a solvent. Heat to reflux for 2 hours. Distill under reduced pressure to remove excess thionyl chloride to obtain light The yellow oil is succinic acid monoethyl chloride (11 g, 98%). The product is directly subjected to the next reaction without separation.

[0060]Take emodin (10g, 37mmol) and triethylamine (2.3g, 22mmol) in a 250mL round-bottomed flask, use dichloromethane (3mL) as a solvent, slowly dropwise add succinic acid monoethyl chloride ( 7g, 40mmol), ...

Embodiment 3

[0063]Example 3 Preparation of emodin succinyl ethyl ester

[0064]Put succinic anhydride (10g, 100mmol) in a 150mL round-bottomed flask, use ethanol (20mL, 434mmol) as the solvent, heat to reflux for 2 hours, distill under reduced pressure to remove excess ethanol to obtain a pale yellow oily monoethyl succinate (14g, 96%), the product was directly subjected to the next reaction without separation.

[0065]Take monoethyl succinate (10g, 68mmol) in a 150mL round bottom flask, use thionyl chloride (20g, 170mmol) as the solvent, heat to reflux for 1 hour, distill under reduced pressure to remove excess thionyl chloride to obtain light The yellow oil is succinic acid monoethyl chloride (8g, 98%). The product is directly subjected to the next reaction without separation.

[0066]Take emodin (10g, 37mmol) and ammonia (1.5g, 44mmol) in a 250mL round-bottomed flask, use dichloromethane (3mL) as the solvent, slowly add succinate monoethyl chloride (8g, 45mmol) at room temperature ), and continue to ...

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PUM

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Abstract

The invention discloses an emodin succinyl ester type compound as well as a preparation method and application thereof. The compound disclosed by the invention has a structure shown as a formula I (wherein, R is C1 to C5 alkyl); preferably, the compound is emodin succinyl ethyl ester. An experiment proves that the emodin succinyl ester type compound disclosed by the invention can be used for promoting the healing of diabetes mellitus wounds better when being compared with emodin, and can be used for preparing a medicine for promoting the healing of the diabetes mellitus wounds. Furthermore, the invention further discloses a method for preparing the compound; the method has a simple route, can effectively shorten the synthesis time and reduce the cost, is simple to operate and easy to implement, so that the method is suitable for industrial production. (The formula I is shown in the description.).

Description

Technical field[0001]The present invention relates to an emodin succinyl ester compound and a preparation method thereof, and also relates to the use of the compound in effectively promoting the healing of diabetic wounds, and also relates to an emodin succinyl ethyl ester oil agent, which is preferably With emodin succinyl ethyl ester as the only active ingredient, it can effectively promote skin tissue repair and wound healing in diabetic patients with significant effects. The invention belongs to the fields of medicine synthesis and medicine and health.Background technique[0002]At present, diabetes has become the third chronic non-communicable disease threatening human health worldwide. my country has the largest number of diabetic patients in the world. In 2016, the estimated prevalence of diabetes diagnosed in accordance with the latest international clinical diagnostic standards in a sample of adults aged 18 and over in my country reached 11.6%. Among diabetic patients, about ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/40C07C67/14C07C67/56C07C67/30C07C69/67C07C67/08C07C69/675A61K31/225A61P17/02A61P3/10A61K9/00A61K47/44A61K9/08
CPCA61K9/0014A61K47/44C07C67/08C07C67/14C07C67/30C07C67/56C07C69/40C07C69/675C07C69/67
Inventor 杨宝峰张勇杜智敏王金辉白云龙吕延杰黄学石
Owner JIANGSU KANION PHARMA CO LTD
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