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The preparation method of vinorelbine tartrate

A technology of vinorelbine tartrate and tartaric acid, which is applied in the field of medicine and can solve the problems affecting the clarity, stability, safety and the like of preparations

Active Publication Date: 2018-10-16
JIANGSU HANSOH PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] The main dosage form of vinorelbine tartrate on the market at home and abroad is injection, and impurities will greatly affect the clarity, stability, safety, etc. of the preparation

Method used

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  • The preparation method of vinorelbine tartrate
  • The preparation method of vinorelbine tartrate
  • The preparation method of vinorelbine tartrate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Add 10mmol of the compound of formula I to 100ml of trifluoroethanol, control the temperature to 0°C, add 10ml of 3mol / L sodium chloride solution of ferric chloride dropwise under stirring, add 10mmol of peracetic acid, and stir at 0°C for reaction 2h, then add 11mmol of ventolin, continue to stir and react at 0°C for 4h; control the temperature to 75°C, continue to add 100ml of 2mol / L sodium acetate solution, then add 40mmol of thiourea dioxide, react at 75°C for 3h, and use dichloromethane Extract with 100mL×3, wash with saturated saline, dry and evaporate the solvent under reduced pressure; continue to add 150ml of acetone and 15mmol of L-tartaric acid to react to form a salt, add anhydrous ether dropwise under stirring until the precipitate is fully separated out, filter, and dry in vacuum to obtain pure white The product is 9.59g, and the product obtained through testing is vinorelbine tartrate (see the attached form for identification data), the product purity is 9...

Embodiment 2

[0041] Add 10mmol of the compound of formula I to 100ml of trifluoroethanol, control the temperature to 0°C, add dropwise 10ml of 3mol / L sodium chloride solution of ferric chloride with stirring, add 10mmol of peroxybenzoic acid, and stir at 0°C React for 2 hours, then add 11 mmol of ventolin, continue to stir the reaction for 4 hours at 0°C; Extract with 100mL×3 methane, wash with saturated saline, dry and evaporate the solvent under reduced pressure; continue to add 150ml of acetone and 15mmol of L-tartaric acid to react to form a salt, add anhydrous ether dropwise under stirring until the precipitate is fully separated, filtered, and vacuum-dried to obtain pure White product 9.67g. 13 The CNMR spectrum is consistent with Table 1 and Table 2, and the detected purity is 95.0%, the ee value is 99.8%, and the molar yield is 85% (based on the compound of formula I).

Embodiment 3

[0043] Add 10mmol of the compound of formula I to 100ml of trifluoroethanol, control the temperature to 0°C, add dropwise 10ml of 3mol / L sodium chloride solution of ferric chloride with stirring, add 10mmol of peroxybenzoic acid, and stir at 0°C React for 2 hours, then add 11 mmol of ventolin, continue to stir the reaction at 0°C for 4 hours; Extract with 100mL×3 methane, wash with saturated saline, dry and evaporate the solvent under reduced pressure; continue to add 150ml of acetone and 15mmol of L-tartaric acid to react to form a salt, add anhydrous ether dropwise under stirring until the precipitate is fully separated, filtered, and vacuum-dried to obtain pure White product 9.78g. 13 The CNMR spectrum is consistent with Table 1 and Table 2, and the detected purity is 99.5%, the ee value is 99.8%, and the molar yield is 90% (based on the compound of formula I).

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Abstract

The invention relates to a preparation method of vinorelbine tartrate. The preparation method comprises the following steps: oxidizing a compound as shown in the formula I by the use of iron chloride and organic peracid, coupling by adding vindoline, carrying out a reduction reaction by adding a reducing agent, letting the reduction reaction product react with L-tartaric acid to form salt so as to prepare vinorelbine tartrate. According to the product obtained by the preparation method, yield is high, and purity and chiral purity (ee value) are very good.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a preparation method of vinorelbine tartrate. Background technique [0002] In the last century, both vinorelbine and the following compound of formula I have been found to have antitumor activity, but the development of the compound of formula I has long been stopped at home and abroad, and vinorelbine has been developed and marketed. [0003] [0004] The preparation method of vinorelbine is basically to obtain dehydrated vinblastine first, and then further prepare it by the following three methods: [0005] (1) Dehydrated vinblastine is chlorinated by N-chlorobenzotriazole, and the resulting chlorinated product is treated with silver fluoroborate to shrink the ring to obtain vinorelbine in the presence of water; [0006] (2) dehydrated vinblastine is oxidized by m-chloroperoxybenzoic acid, and then treated with trifluoroacetic anhydride for ring opening and rearrangement to obtain ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D519/04
CPCC07D519/04
Inventor 陈刚胜胡春勇李琴王春玲
Owner JIANGSU HANSOH PHARMA CO LTD
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