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Tigecycline purification method

A technology of tigecycline and purification method, which is applied in the field of medicinal chemistry, can solve problems such as not being able to meet quality standards, and achieve the effect of high yield

Inactive Publication Date: 2017-09-01
HEBEI SHENGXUE DACHENG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is reported that the purity of the product obtained by this method is more than 98%, and the single impurity is less than 0.5%, but it still cannot meet the requirements of quality standards

Method used

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  • Tigecycline purification method
  • Tigecycline purification method
  • Tigecycline purification method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Add 10g, 0.03mol of aminominocycline hydrochloride to 0-5°C, 75ml of deionized water, and add 16g, 0.1mol of tert-butylaminoglycyl chloride hydrochloride in portions under nitrogen protection, and stir to react 1h, after the reaction is complete, add 14% ammonia water to adjust the pH to 7.2, add methanol 140ml, and extract with an organic solvent of a mixture of ether, ethyl acetate, n-heptane and petroleum ether, and then add 3% ammonia water to adjust the pH to 7.2 , after stirring for 15 minutes, the liquids were separated, the aqueous phase was extracted with a mixed aqueous solution of methanol, ethanol and acetone, the organic phases were combined, washed 2 to 4 times with 40-50% methanol, dried over anhydrous sodium sulfate and filtered, and the filter cake was washed with two Wash with methyl chloride, combine the filtrate and lotion, concentrate under reduced pressure at 25-35°C, and obtain crude tigecycline as a brown solid after vacuum drying. Add the crude t...

Embodiment 2

[0024] Add 14g, 0.03mol of aminominocycline hydrochloride to 0-5°C, 75ml of deionized water, and add 20g, 0.1mol of tert-butylaminoglycyl chloride hydrochloride in portions under nitrogen protection, and stir to react 1.2h, after the reaction is complete, add 20% ammonia water to adjust the pH to 7.2, add methanol 200ml, and extract with an organic solvent of a mixture of ether, ethyl acetate, n-heptane and petroleum ether, then add 9% ammonia water to adjust the pH to 7.2, after stirring for 20 minutes, separate the liquids, extract the aqueous phase with a mixed aqueous solution of methanol, ethanol and acetone, combine the organic phases, wash with 50% methanol for 3 times, dry with anhydrous sodium sulfate overnight and filter, and wash the filter cake with dichloromethane , combined the filtrate and lotion, concentrated under reduced pressure at 28°C, and obtained brown solid tigecycline crude product after vacuum drying, added the crude tigecycline product to 100ml of eth...

Embodiment 3

[0027] Example 3 Aminominocycline hydrochloride 14g, 0.03mol was added to 0-5°C, 75ml of deionized water, and tert-butylaminoglycyl chloride hydrochloride 18g, 0.1mol was added in portions under nitrogen protection , stirred and reacted for 1.5h, after the reaction was complete, add 18% ammonia water to adjust the pH to 7.2, add methanol 140ml, and extract with an organic solvent of a mixture of ether, ethyl acetate, n-heptane and petroleum ether, and then add 6% ammonia water Adjust the pH to 7.2, stir for 18 minutes, then separate the liquids, extract the aqueous phase with a mixed aqueous solution of methanol, ethanol and acetone, combine the organic phases, wash 4 times with 45% methanol, dry overnight with anhydrous sodium sulfate, and filter the filter cake with two Wash with methyl chloride, combine the filtrate and lotion, concentrate under reduced pressure at 30°C, and obtain the crude product of tigecycline as a brown solid after vacuum drying. Add the crude product o...

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Abstract

The invention discloses a tigecycline purification method in the technical field of pharmaceutical chemistry. The tigecycline purification method specifically comprises the following steps: S1. adding amino minocycline hydrochloride and tertbutyl-amino glycine chloride hydrochloride, and stirring for reacting; S2. after the reaction is complete, adding 14-20% ammonia water for regulating the pH to be 7.2; S3. combining an organic phase; S4. combining filtrate and washing liquor, and performing vacuum drying to obtain brown solid crude tigecycline; S5. filtering the crude tigecycline; and S6. crystalizing the filtered filter cakes with 2-butanol, and performing decompressed drying to obtain golden yellow solid refined tigecycline. The tigecycline purification method has the advantages of being high in yield, simple in technology and easy to control, the tigecycline meeting the quality standard can be obtained by simply concentrating, filtering and drying the washing liquor.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a method for purifying tigecycline. Background technique [0002] Tigecycline is an anti-infective drug, which is a fully synthetic drug synthesized from minocycline. At present, the quality standard of tigecycline has been included in the Pharmacopoeia USP38, in which the requirements for various impurities are relatively high, so the purification of tigecycline is a difficult point in the production of tigecycline. The reported purification methods of tigecycline include: 1. The crude product of tigecycline is mixed and stirred for several hours with at least two polar protic solvents, and then filtered to obtain the tigecycline product. The product purity of this method is more than 99.0%, and the maximum single impurity is less than 0.1%, but the product quality does not meet the pharmacopoeia standard and the use of mixed protic solvents causes solvent recovery ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/14C07C231/24C07C237/26
CPCC07B2200/07C07C231/14C07C231/24C07C237/26
Inventor 王婷宋志倩张云钊郝立波
Owner HEBEI SHENGXUE DACHENG PHARMA
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