Continuous chromatographic resolution method of guaifenesin racemate

A technology of guaiacol glyceryl ether and racemate, applied in the field of separation of chiral drugs

Inactive Publication Date: 2017-03-15
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As mentioned above, the method of synchronously controlling the simulated moving bed to continuously split the racemate of guaiacol glyceryl ether has been reported by the predecessors, and other operating modes have not been reported at home and abroad.

Method used

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  • Continuous chromatographic resolution method of guaifenesin racemate
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  • Continuous chromatographic resolution method of guaifenesin racemate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1. Simultaneous control of simulated moving bed for continuous resolution of guaiacol racemate

[0047] The simulated moving bed equipment includes injection pump, elution pump, extraction pump, raffinate pump, circulation pump, packed column, control valve, online detector, temperature controller and computer automatic control system. The material liquid and the eluent enter the simulated moving bed system through the feed port and the eluent port respectively, and the two enantiomers of guaiacol glyceryl ether flow out from the two outlets of the extract liquid and the raffinate liquid respectively. At regular intervals, the feed liquid and eluent inlets and the extract liquid and raffinate outlets are simultaneously switched to the next packed column along the flow direction of the mobile phase, and switched in turn.

[0048]Racemic guaiacol, with a purity of 99.0%, was purchased from TCI (Shanghai) Chemical Industry Development Co., Ltd. The mobile phase an...

Embodiment 2

[0051] Embodiment 2.Modicon process continuously splits guaiacol glyceryl ether racemate

[0052] On the basis of synchronous control simulated moving bed (SMB process) research, the separation performance of Modicon process was evaluated.

[0053] The SMB process of above-mentioned implementation adopts 6 packed columns, and feed concentration and feed speed are constant when the inlet and outlet positions are switched periodically, and are constant at 8.0mg / ml (racemate) and 3.5ml / min. The Modicom process adopts changing the feed concentration to improve the separation efficiency. The cycle switching time of the inlet and outlet positions is still 2.5 minutes, but for the first 1.25 minutes, a low-concentration feed (such as 2.0 mg / ml) is used, and after 1.25 minutes, a high-concentration feed is used. (such as 14.0mg / ml), the average feed concentration in the switching cycle is 8.0mg / ml (racemate). Using the Modicon process, the guaiacol racemate can be continuously separa...

Embodiment 3

[0054] Embodiment 3. Powerfeed process continuously splits guaiacol glyceryl ether racemate

[0055] On the basis of synchronously controlled simulated moving bed (SMB process) research, the separation performance of Powerfeed process was evaluated.

[0056] Also in the 6 packed column SMB processes implemented above, the feed rate is constant at 3.5ml / min and the feed concentration is constant at 8.0mg / ml (racemate) during the synchronous periodic switching of the inlet and outlet positions. The Powerfeed process uses varying feed rates to improve separation performance. The cycle switching time of the inlet and outlet positions is still 2.5min, but for the first 1.25min, a high feed flow rate (such as 7.0ml / min) is adopted, and for the next 1.25min, a low feed flow rate (such as 0ml / min) is adopted, and the average The feed rate was still 3.5ml / min. In order to compare with the SMB process, the mobile phase flow rate of Zone I and Zone II is the same as that of the SMB pro...

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Abstract

The invention relates to a countercurrent continuous chromatographic resolution method of a guaifenesin racemate. The method utilizes simulated moving bed chromatography to realize continuous separation and comprises one or more of a synchronous control process (SMB), an asynchronous control process (Varicol), a feed rate periodic change process (Powerfeed) and a feed concentration periodic change process (Modicon). When silica gel coated with cellulose-tris(3, 5-dimethylphenylcarbamate) is used as a chiral stationary phase and a mixture of n-hexane and ethanol is used as a mobile phase, the method can continuously and efficiently resolve a guaifenesin racemate, acquire a R-guaifenesin racemate enantiomer and a S-guaifenesin racemate enantiomer with high purity (greater than 99%) and meet the pharmaceutical market standards. The method has a high degree of production automation, high production efficiency and simple processes. In the whole process, the solvent can be recycled so that a cost is low and pollution is avoided.

Description

technical field [0001] The invention relates to the technical field of separation of chiral drugs, in particular to a method for continuously separating racemates of guaiacol glyceryl ether by using a simulated moving bed chromatography technique in multiple operating modes. Background technique [0002] Guaifenesin, the chemical formula is 3-(2-methoxyphenoxy)propane-1,2-diol, the English name is Guaifenesin, it is an expectorant, which has the effects of antitussive and antispasmodic . It is widely used in over-the-counter medicines, with definite curative effect and small side effects. Guaifenesin is the only expectorant drug approved by the FDA in the United States. It has a good sales volume in the antitussive and expectorant drug market in the United States and is widely praised by patients. Guaifenesin is combined with other antitussive and antiasthmatic drugs or formulated into compound applications, such as compound licorice oral liquid, which has a domestic marke...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/36C07C43/23
CPCC07C41/36C07B2200/07C07C43/23
Inventor 李平于建国龚如金
Owner EAST CHINA UNIV OF SCI & TECH
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