Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Pegylated phenol red, preparation method and application thereof

A technology of PEGylated phenol red and polyethylene glycol monomethyl ether, applied in the field of medicine, can solve the problem of low intestinal permeability of biocompatibility, and achieves the reduction of intestinal permeability, wide application, The effect of high product purity

Active Publication Date: 2020-06-02
SHENYANG PHARMA UNIVERSITY
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are relatively few domestic studies on polyethylene glycol-modified small molecule technology. In the absence of existing related technologies, a kind of biocompatibility, high stability, low intestinal permeability, and applicable PEGylated phenol red with advantages such as large-scale production is still a challenging and practical problem

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
  • Pegylated phenol red, preparation method and application thereof
  • Pegylated phenol red, preparation method and application thereof
  • Pegylated phenol red, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] 1. Use methoxypolyethylene glycol-p-toluenesulfonate (average molecular weight 4100) as a starting material to prepare methoxypolyethylene glycolated phenol red

[0063] Preparation and purification of methoxypolyethylene glycol-p-toluenesulfonate

[0064] Take 2 g of polyethylene glycol monomethyl ether (average molecular weight 4000) and dissolve it in 10 mL of dichloromethane, then add 0.2 g of p-toluenesulfonyl chloride, stir magnetically under nitrogen protection, slowly add 0.8 mL of triethylamine dropwise on the ice bath, drop After the addition was completed, the reaction was carried out at room temperature for 12 hours, and the reaction was stopped. Add 10ml of 1M hydrochloric acid until the reaction solution is acidic, extract the aqueous phase with dichloromethane (40mL*3), combine the organic phases, wash with saturated brine (20mL*2), dry, concentrate under reduced pressure, and recrystallize with ether to obtain a white solid , dried in vacuo to constant ...

Embodiment 2

[0068] 1. Preparation and purification of methoxypolyethylene glycol-p-toluenesulfonate (average molecular weight 8100)

[0069] Take 2 g of polyethylene glycol monomethyl ether (average molecular weight 8000) and dissolve it in 10 mL of dichloromethane, then add 0.1 g of p-toluenesulfonyl chloride, stir magnetically under the protection of nitrogen, slowly add 0.4 mL of triethylamine dropwise on the ice bath, drop After the addition was completed, the reaction was carried out at room temperature for 12 hours, and the reaction was stopped. Add 6 mL of 1M hydrochloric acid until the reaction solution is acidic, extract the aqueous phase with dichloromethane (40 mL*3), combine the organic phases, wash with saturated brine (20 mL*2), dry, concentrate under reduced pressure, and recrystallize with ether to obtain a white solid , dried in vacuo to constant weight to obtain a white solid powder, which is p-toluenesulfonylated polyethylene glycol monomethyl ether. The yield is 90%. ...

Embodiment 3

[0073] 1. Preparation and purification of methoxypolyethylene glycol methanesulfonate (average molecular weight 5100)

[0074] Dissolve 2 g of polyethylene glycol monomethyl ether (average molecular weight 5000) in 10 mL of dichloromethane, then add 0.1 g of methylsulfonyl chloride, stir magnetically under nitrogen protection, slowly add 0.4 mL of triethylamine dropwise on an ice bath, After the dropwise addition, react at room temperature for 12 hours and stop the reaction. Add 6 mL of 1M hydrochloric acid until the reaction solution is acidic, extract the aqueous phase with dichloromethane (40 mL*3), combine the organic phases, wash with saturated brine (20 mL*2), dry, concentrate under reduced pressure, and recrystallize with ether to obtain a white solid , vacuum dried to constant weight to obtain a white solid powder, which is methoxypolyethylene glycol-methylsulfonate. The yield was 83%.

[0075] 2. Preparation and purification of methoxy-PEGylated phenol red

[0076]...

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

PropertyMeasurementUnit
molecular weightaaaaaaaaaa
molecular weightaaaaaaaaaa
Login to View More

Abstract

The invention belongs to the technical field of medicines, and relates to pegylated phenol red, a preparation method and application thereof, wherein the polymer is formed by connecting a small molecular drug phenol red and one end of polyethylene glycol (PEG) through a covalent bond, the phenolic hydroxyl group on the phenol red is covalently connected with the long chain of the polyethylene glycol derivative through an ether bond, the structure of the polymer is in the specification under different pH conditions, and n and R are defined in the claims and the specification. The invention alsoprovides a preparation method of the pegylated phenol red. The invention further discloses that the pegylated phenol red has an accurate moisture correction effect when being applied to a body intestinal absorption test. The method has the advantages of easily available raw materials, simple operation, wide application range and environmental protection reaction.

Description

technical field [0001] The invention belongs to the field of medicine, and relates to pegylated phenol red and its preparation method and medical application, in particular to a novel phenol red polymer pegylated phenol red and its preparation method and in the water correction of in vivo intestinal absorption test the use of. Background technique [0002] In vivo one-way intestinal perfusion and in vivo intestinal circulation are the most commonly used methods for studying drug absorption in vivo, which are closest to the real absorption state in vivo. They can be used to investigate the degree of drug absorption, absorption mechanism, and the influence of excipients on drug penetration. Research on the transport ability, mechanism and toxicity of drug absorption enhancers. When studying the intestinal absorption mechanism of drugs, since the small intestine not only absorbs drugs but also absorbs or secretes water, the volume of perfusate changes, so the method of calcula...

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): C08G65/334G01N15/08
CPCC08G65/3346G01N15/00G01N15/08G01N15/01Y02P20/55
Inventor 程刚安桐刘永祥
Owner SHENYANG PHARMA UNIVERSITY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com