Emodin succinyl ester type compound as well as preparation method and application thereof

A technology of emodin succinyl ester and emodin succinyl ethyl ester is applied in the fields of drug synthesis and medicine and health, and can solve the problems of high toxicity and poor absorption, and achieves the advantages of low cost, less use, and promotion of skin tissue wound repair. Effect

Active Publication Date: 2018-05-18
JIANGSU KANION PHARMA CO LTD
View PDF1 Cites 6 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Emodin succinyl ester type compound as well as preparation method and application thereof
  • Emodin succinyl ester type compound as well as preparation method and application thereof
  • Emodin succinyl ester type compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] The preparation of embodiment 1 emodin ethyl succinate

[0051] Take succinic anhydride (1.0g, 10mmol) and place it in a 10mL round-bottomed flask, use ethanol (3.5mL, 60mmol) as a solvent, heat and reflux for 4 hours, and distill off excess ethanol under reduced pressure to obtain a light yellow oil, namely succinic acid mono Ethyl ester (1.4 g, 96%), this product was carried on to the next reaction without isolation.

[0052] Get monoethyl succinate (1.0g, 6.8mmol) and place in a 10mL round-bottomed flask, use thionyl chloride (4.0g, 34.0mmol) as solvent, heat to reflux for 2 hours, and remove excess oxychloride by distillation under reduced pressure. The sulfone was obtained as a light yellow oily product, namely ethyl succinic acid chloride (1.1 g, 98%), and the product was directly carried on 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 solve...

Embodiment 2

[0057] The preparation of embodiment 2 emodin ethyl succinate

[0058] Take succinic anhydride (10g, 100mmol) and place it in a 150mL round-bottomed flask, use ethanol (40mL, 600mmol) as a solvent, heat and reflux for 6 hours, and distill off excess ethanol under reduced pressure to obtain a light yellow oil that is monoethyl succinate (14 g, 96%), the product was directly carried on to the next reaction without isolation.

[0059] Get monoethyl succinate (10g, 68mmol) and place in a 150mL round-bottomed flask, use thionyl chloride (40g, 340mmol) as a solvent, heat and reflux for 2 hours, and remove excess thionyl chloride by distillation under reduced pressure to obtain light The yellow oil was succinic acid monoethyl chloride (11 g, 98%), and the product was directly carried on to the next reaction without isolation.

[0060] Get emodin (10g, 37mmol) and triethylamine (2.3g, 22mmol) and place in a 250mL round-bottomed flask, use dichloromethane (3mL) as solvent, slowly drop...

Embodiment 3

[0063] The preparation of embodiment 3 emodin ethyl succinate

[0064] Take succinic anhydride (10g, 100mmol) and place it in a 150mL round-bottomed flask, use ethanol (20mL, 434mmol) as a solvent, heat and reflux for 2 hours, and distill off excess ethanol under reduced pressure to obtain a light yellow oil that is monoethyl succinate (14 g, 96%), the product was directly carried on to the next reaction without isolation.

[0065] Get monoethyl succinate (10g, 68mmol) and place in a 150mL round-bottomed flask, use thionyl chloride (20g, 170mmol) as a solvent, heat and reflux for 1 hour, and remove excess thionyl chloride by distillation under reduced pressure to obtain light The yellow oil was succinic acid monoethyl chloride (8 g, 98%), and the product was directly carried on to the next reaction without isolation.

[0066] Take emodin (10g, 37mmol) and ammonia water (1.5g, 44mmol) and place in a 250mL round-bottomed flask, use dichloromethane (3mL) as solvent, slowly add s...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

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 application of the compound in effectively promoting diabetic wound healing, and also relates to an emodin succinyl ethyl ester oil, 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, and the effect is remarkable. The invention belongs to the fields of drug synthesis and medical hygiene. Background technique [0002] At present, diabetes has become the third major chronic non-communicable disease threatening human health in the world. my country is the country with the largest number of diabetic patients in the world. In 2016, the estimated prevalence rate of diabetes diagnosed according to the latest international clinical diagnostic standards reached 11.6% among adult samples aged 18 and over in my country. A...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/40C07C67/14C07C67/56C07C67/30C07C69/67C07C67/08C07C69/675A61K31/225A61P17/02A61P3/10A61K9/00A61K47/44
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap