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Method of purification of prostaglandins including fluorine atoms by preparative high performance liquid chromatography

A technology of tafluprostaglandin and prostaglandin, which is applied in the field of purifying fluorine-containing prostaglandin by preparative high performance liquid chromatography, can solve the problems of separation and removal of impurities, and achieve the effect of overcoming the purification problem

Inactive Publication Date: 2014-02-19
EVERLIGHT CHEMICAL INDUSTRIAL CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Travoprost and tafluprost are similar in structure, and they also have fluorine atoms in the molecule, and there is also the problem of separation and removal of impurities. Therefore, it is urgent to develop a new purification method to achieve high-quality liquid raw materials

Method used

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  • Method of purification of prostaglandins including fluorine atoms by preparative high performance liquid chromatography
  • Method of purification of prostaglandins including fluorine atoms by preparative high performance liquid chromatography
  • Method of purification of prostaglandins including fluorine atoms by preparative high performance liquid chromatography

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preparation example 1

[0033]

[0034] Add 2-oxo-3-phenoxypropyl phosphate dimethyl (Dimethyl 2-oxo-3-phenoxypropylphosphonate) (9g) and tetrahydrofuran (Tetrahydrofuran) (60g) into the reaction bottle and mix and dissolve, and tap water (4.5 g) Dissolving lithium hydroxide (LiOH·H 2 O) (1.4g) was then added to the reaction flask and reacted at room temperature for 1 hour. Dissolve (1S, 5R, 6R, 7R)-6-formyl-7-benzoylhydroxyl-2-oxabicyclo[3,3,0]oct-3-one ((1S, 5R ,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3,3,0]octan-3-one) (9g) was added to the reaction flask, and reacted at room temperature for 1.5-2 hours. After the reaction, add hydrochloric acid (HCl) aqueous solution to neutralize, concentrate and extract with ethyl acetate and sodium bicarbonate aqueous solution, the organic layer is dehydrated and concentrated, then purified by crystallization to obtain 8g (1S, 5R, 6R, 7R) -2-oxa-7-benzoyl hydroxy-6-[(1E)-4-phenoxy-3-oxygen-1-butenyl]bicyclo[3,3,0]oct-3-one ( (1S, 5R, 6R, 7R)-2-oxa-7-ben...

Embodiment 1

[0041]

[0042] Tafluprost was dissolved in isopropanol / n-hexane = 1:1 (v / v) solution, purified using Varian SepTech Si60 (10 μm) as the stationary phase, and the composition of the eluate was isopropanol / n-hexane (IPA / Hexane)=7:93 (v / v), the flow rate is 266ml / min, and the pressure is about 20bar.

Embodiment 2-4

[0050]

[0051] The crude travoprost products prepared sequentially were purified in Examples 2-4 respectively. Its purification method using preparative HPLC is as follows. The crude product of travoprost was dissolved in isopropanol, and purified using Varian SepTech Si60 (10 μm) as the stationary phase, and the composition of the eluate was ethanol / n-hexane (EtOH / Hexane)=5:95 (v / v ), the flow rate is 266ml / min, and the pressure is about 20bar.

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Abstract

The present invention discloses a method of purification of prostaglandins including fluorine atoms by using preparative HPLC. Tafluprost and Travoprost are prostaglandins including fluorine. The chemical structure of the impurities in crude Tafluprost and crude Travoprost also contain fluorine, therefore, the removal of the impurities is difficult. Purification by using preparative high performance liquid chromatography (HPLC) can achieve high-quality liquid bulk drugs.

Description

technical field [0001] The invention relates to a method for purifying prostaglandins, in particular to a method for purifying fluorine-containing prostaglandins by using preparative high performance liquid chromatography. Background technique [0002] Natural prostaglandins (prostaglandins) are biologically active substances synthesized in the body and cells, which can be used to reduce the pressure in the eyes as a drug for the treatment of high intraocular pressure and glaucoma. However, they are irritating to the eyes and have inflammatory effects. Side effects, easy to cause damage to the cornea. [0003] 16-phenoxy-15-deoxy-15,15-difluoro-17,18,19,20-tetraprostaglandin F 2α Isopropyl ester, also known as: tafluprostaglandin (16-phenoxy-15-deoxy-15, 15-difluoro-17, 18, 19, 20-tetranorprostaglandin F 2α isopropyl ester, Tafluprost) was discovered by Santen Company, its effect on lowering intraocular pressure is better than that of known prostaglandins, it has a long-l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C405/00
CPCC07C67/58C07C67/56C07C405/00C07C2601/08C07C69/736
Inventor 蔡嘉忠陈虔郁梁森堡罗于其姚启祥
Owner EVERLIGHT CHEMICAL INDUSTRIAL CORPORATION
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