Unlock instant, AI-driven research and patent intelligence for your innovation.

Chiral resolution of prazole compound by aqueous two-phase system

A two-phase system, technology of azole compounds, applied in the field of medicine and chemical industry, can solve the problems such as chiral separation that has not been deeply researched and applied, no application of chiral separation of prazole compounds, environmental pressure, etc.

Active Publication Date: 2014-07-16
HUNAN RHON PHARMA
View PDF7 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Water-organic dual-phase extraction has been widely studied and initially applied in chiral separation, but it uses a large amount of solvents such as dichloromethane, which puts a lot of pressure on the environment
Chinese patent 200910044102.2 discloses an extraction system that uses a water-organic two-phase system to identify chiral extraction and separate enantiomers of aromatic acid compounds, but does not involve the resolution of pyrazole compounds
[0006] In contrast, aqueous two-phase extraction technology is more environmentally friendly and safe, and has been widely used in natural product separation and other fields, but it has not been deeply studied and applied in chiral resolution, nor has it been used in chiral resolution of prazoles. Aspects of application

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0013] The following specific embodiments are intended to explain the content of the present invention.

[0014] 1. Add 1.0 g of omeprazole and 2.0 g of β-cyclodextrin into 10 ml of ammonia buffer solution with pH 11.0. Add 20ml of 40% ethanol solution containing 2g of diisopropyl tartrate, and stir evenly. Slowly and uniformly add 3.0 g of ammonium sulfate, stir evenly, and stir at high speed for 30 minutes. After standing for 30 minutes, the layers were separated and the two phases were separated. Adjust the pH of the ethanol phase to 7.0 with glacial acetic acid, crystallize, centrifuge, and dry at low temperature to obtain the R-omeprazole chiral compound with an ee value of 99.3%. The ethanol phase can be concentrated and extracted with an equal amount of toluene, and crystallized at low temperature. Centrifuge to recover part of the R-omeprazole chiral compound. Adjust the pH of the water phase to 7.0 with glacial acetic acid, crystallize, centrifuge, and dry at 45°C ...

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 a new method for chiral resolution and racemization of a prazole compound, and particularly an aqueous two-phase resolution system is adopted. An aqueous phase contains a hydrophilic chiral resolving agent and the prazole compound, and the other phase contains an alcohol soluble chiral resolving agent; after the two phases are mixed, the pH is adjusted to neutral, and the prazole compound is resolved into optical-pure chiral compounds under the actions of the two chiral resolving agents. When a phase-separating salt is added into the system, the system can become two separable phases respectively containing two different chiral isomers.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and in particular relates to the chiral resolution of merazole compounds. [0002] Background technique [0003] Prazoles are a class of proton pump inhibitors, which reduce gastric acid secretion and prevent the formation of gastric acid by inhibiting the H+ / K+-ATPase of gastric parietal cells. They are used to treat diseases such as gastric ulcer and esophageal reflux. Omeprazole, pantoprazole, lansoprazole, rabeprazole, etc. Since there is a sulfoxide group in its molecular structure, and the sulfur atom in it has chirality, it is a racemate of a pair of optical isomers. The pharmacological effect is often only one of the isomers, and the other basically has no pharmacological activity or has side effects, so its chiral resolution is of great significance in application. The currently listed esomeprazole is omeprazole The levoisomer of meprazole has better pharmacological activ...

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
IPC IPC(8): C07B57/00C07D401/12
Inventor 夏钊李光唐亮
Owner HUNAN RHON PHARMA