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A kind of purification method of homoharringtonine

A technology of homoharringtonine and a purification method, which is applied in the field of separation and purification of homoharringtonine, can solve the problems of unfavorable industrial production, complicated operation and high cost, and achieves the advantages of being beneficial to industrial production, improving yield and simplifying operation. Effect

Active Publication Date: 2016-08-17
CHONGQING TAIHAO PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Among the currently disclosed column chromatography methods, most of the reversed-phase column chromatography is used, and aluminum oxide is used as the stationary phase, and the mixed aqueous solution of chloroform / methanol or alcohol and phosphate buffer solution is used as the mobile phase for separation. Equipment, high cost, cumbersome operation, not conducive to industrial production, especially when the mixed aqueous solution of alcohol and phosphate buffer solution is used as the mobile phase, it is necessary to control the pH value within an appropriate range
In addition, in the recrystallization step after column chromatography, the existing technology basically uses methanol, methanol / water, and ether as the recrystallization solvent, and the recrystallization yield of the obtained homoharringtonine is at most about 80%. lower

Method used

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  • A kind of purification method of homoharringtonine
  • A kind of purification method of homoharringtonine
  • A kind of purification method of homoharringtonine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Dissolve 15 g of homoharringtonine crude product with a purity of about 11% in a small amount of ethyl acetate: n-hexane: DIEA=4:1:0.005, add it to a 300 g silica gel column with a size of 300 mesh, and use ethyl acetate: The solution of n-hexane: DIEA=4:1:0.005 is used as the mobile phase, separated by column chromatography, tracked by thin-layer chromatography or HPLC, and the chromatographic solution containing homoharringtonine is collected and concentrated in vacuo to obtain a purity of ≥50%. The solid, its HPLC spectrum sees figure 1 . Repeat the steps of the first column chromatography, dissolve the solid after the first column chromatography, use ethyl acetate:n-hexane:DIEA=4:1:0.005 solution as mobile phase, and carry out silica gel column chromatography separation , collect the chromatographic solution containing homoharringtonine, concentrate in vacuo to solid, dissolve the solid with methanol and then spin dry to obtain a solid with a purity of 90%. Its HPL...

Embodiment 2

[0044] Dissolve 15 g of homoharringtonine crude product with a purity of about 15% in a small amount of ethyl acetate: n-hexane: DIEA=1:1:0.001, add to 1200 g of silica gel column with a size of 160 mesh, and use ethyl acetate: n-Hexane: DIEA = 1:1:0.001 solution as the mobile phase, separated by column chromatography, tracked by thin-layer chromatography or HPLC, collected the chromatographic solution containing homoharringtonine, concentrated in vacuo, and obtained a purity of ≥52% s solid type. Repeat the steps of the first column chromatography, dissolve the solid after the first column chromatography, use ethyl acetate: n-hexane: DIEA = 1:1:0.001 solution as mobile phase, and carry out silica gel column chromatography separation , the chromatographic solution containing homoharringtonine was collected, concentrated in vacuo to a solid, dissolved in methanol and then spin-dried to obtain a solid substance with a purity of 91%.

[0045] Dissolve 2.2 g of the solid after tw...

Embodiment 3

[0049] Dissolve 15 g of homoharringtonine crude product with a purity of about 20% in a small amount of ethyl acetate: n-hexane: DIEA=3:1:0.01, add to 600 g of 200-mesh silica gel column, and use ethyl acetate: n-Hexane: DIEA = 3:1:0.01 solution as mobile phase, separated by column chromatography, tracked by thin-layer chromatography or HPLC, collected the chromatographic solution containing homoharringtonine, concentrated in vacuo to obtain a purity of ≥55% s solid type. Repeat the steps of the first column chromatography, dissolve the solid after the first column chromatography, use ethyl acetate: n-hexane: DIEA = 3:1:0.01 solution as mobile phase, and carry out silica gel column chromatography separation , the chromatographic solution containing homoharringtonine was collected, concentrated in vacuo to a solid, dissolved in methanol and then spin-dried to obtain a solid substance with a purity of 93%.

[0050] Dissolve 2.9 g of the solid after two column chromatography wit...

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Abstract

The invention relates to the field of pharmaceutical chemistry and in particular discloses a method for purifying homoharringtonine. The method for purifying homoharringtonine comprises the following steps: dissolving crude homoharringtonine by a mobile phase, taking silica gel as a stationary phase and taking a mixed solution of ethyl acetate, normal hexane and DIEA (Diisopropylethylamine) as the mobile phase to carry out column chromatography, collecting a chromatographic solution containing homoharringtonine, and concentrating the chromatographic solution into solid; dissolving the solid by using ethyl acetate, then adding normal hexane or n-heptane, uniformly mixing, standing and crystallizing, carrying out suction filtration, drying filter cake to obtain homoharringtonine solid. According to the method for purifying homoharringtonine, the common silica gel is used for replacing aluminum oxide in reversed phase chromatography and is taken as the stationary phase; the proper mobile phase is selected by taking the stationary phase as a basis and cooperates with subsequent optimally-matched organic solvents for re-crystallizing; the purity of the purified homoharringtonine is greater than 99.5%; the re-crystallizing yield is increased to 90-95%; the operation is simplified; the cost is lowered; the industrial production is facilitated.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a method for separating and purifying homoharringtonine. Background technique [0002] Homoharringtonine (Homoharringtonine, HHT), also known as Homoharringtonine, Homoharringtonine, Gaomatalintonine, the molecular formula is C 29 h 39 NO 9 , which is off-white or light yellow crystalline powder or amorphous loose solid, which has the structure shown in formula I: [0003] [0004] Homoharringtonine is an effective anticancer drug isolated from the endemic Herringbone genus in my country. It has been used for acute myeloid leukemia (AML) and chronic myeloid leukemia ( CML) clinical treatment, the curative effect is remarkable. Homoharringtonine is a tetracycline alkaloid drug with multiple anti-tumor effects. It is a cycle-specific anti-tumor drug. Depolymerize ribosomes, inhibit protein synthesis, reduce tumor cell division index, and decrease tumor tissue nucleic acid ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/20
CPCC07D491/20
Inventor 王信见吴进杨晓秋
Owner CHONGQING TAIHAO PHARM CO LTD
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