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Purification method of ulipristal acetate

A purification method and patented technology, applied in the field of purification of ulipristal acetate, can solve the problems of increased demethylated impurities, large N-demethylated impurities, incomplete drying, etc.

Inactive Publication Date: 2015-08-26
NANJING HEALTHNICE MEDICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Direct heating and refining with ethanol and isopropanol can effectively remove intermediates and rearrangement impurities, but the N-demethylation impurities are relatively large. The reason for the analysis may be that the crude oily product obtained after washing with weak base sodium acetate is not dry enough. For reasons such as thoroughness, a small amount of sodium acetate remains in the crude oil product (demethylation impurities are easily produced under alkaline conditions), and when ethanol and isopropanol are used for recrystallization, heating to 65-70°C will lead to increased demethylation impurities to about 1%

Method used

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  • Purification method of ulipristal acetate
  • Purification method of ulipristal acetate
  • Purification method of ulipristal acetate

Examples

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Effect test

Embodiment 1

[0011] Purification of compound formula (I) 17α-(acetyloxy)-11β-(4-N,N-dimethylaminophenyl)-19-norpregna-4,9-diene-3,20-dione Crude.

[0012] In a 20L glass reactor, dissolve 1.44kg of oily matter with 2.9L (2.61kg) of ethyl acetate, heat to 45°C, slowly add 8.65L (5.88kg) of n-heptane dropwise at this temperature, crystals slowly precipitate out, add After that, cool to room temperature, then crystallize at 5-10°C for 16 hours, filter, and dry the filter cake at 40°C with blast air to obtain 780.11g of light yellow crystalline powder (single-step yield 64%, yield range: 60%- 65%). In a 10L glass reactor, heat 780.11g of light yellow crystals with 3.9L (3.08kg) of absolute ethanol to 65-70°C to dissolve. After adding, cool to room temperature, then crystallize at 5-10°C for 16 hours, filter, The filter cake was air-dried at 40° C. to obtain 665.21 g of light yellow crystalline powder (85% yield in one step), 43%-47%.

[0013] (Based on intermediate 2).

Embodiment 2

[0015] Most reports in the literature have been purified by column method, which is not suitable for industrial production. Based on the impurity distribution and solubility of the crude product, the solvents were screened, and the purification effects of different solvents are compared in Table 1.

[0016] Table 1 Comparison of purification effects of different solvents

[0017]

[0018] As can be seen from the above table, it can be seen that the impurity content of the product obtained by the refining method of the present invention (ethyl acetate: n-heptane=3: 1) is obviously lower than other refining methods, and the maximum single impurity can be less than 0.05% when secondary refining with ethanol , the total impurity is less than 1.0%.

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Abstract

The invention provides a method for purifying 17 alpha-(acetoxyl)-11 beta-(4-N,N- dimethylaminophenyl)-19-norpregna-4,9-diene-3,20-diketone. The method is simple to operate, a used solvent is non-toxic, and the impurity removing effect is better.

Description

technical field [0001] The present invention relates to compound formula (I) 17α-(acetyloxy)-11β-(4-N, N-dimethylaminophenyl)-19-norpregna-4,9-diene-3,20- Diketone purification method. [0002] Background technique [0003] Ulipristal acetate, trade name Ella, as a progesterone agonist / antagonist indicated for the prevention of pregnancy after unprotected intercourse or for known or suspected contraceptive failure, May 2009, the product was launched in Europe Marketed under the brand name Ella One, it was approved by the FDA in August 2010 under the trade name Ella. [0004] In U.S. Patent No. 4,954,490 and U.S. No. 5,929,262, the synthesis of the above-mentioned compound was reported, and a yellow crystalline substance was obtained. The detailed purification method was not reported, and the obtained yellow crystalline substance contained more impurities. Domestic patent CN102516345 reported the use of ethanol and isopropanol Directly purify the crude product, although ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J41/00
CPCC07J41/0005
Inventor 赵思云王华娟
Owner NANJING HEALTHNICE MEDICAL TECH
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