Ropivacaine hydrochloride impurity and preparation method thereof

A technology of ropivacaine hydrochloride and impurities, which is applied in the field of ropivacaine hydrochloride impurities and its preparation, can solve the problems affecting the efficacy of drugs, affecting the purity of ropivacaine hydrochloride, toxic and side effects, etc., and achieve the reduction of quality control analysis Cost, excellent anesthesia performance, simple operation effect

Active Publication Date: 2020-11-13
GUANGDONG JIABO PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The impurities that may be produced during the production and storage of ropivacaine hydrochloride not only affect the purity of ropivacaine hydrochloride, but also affect the efficacy of the drug and may cause toxic and side effects

Method used

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  • Ropivacaine hydrochloride impurity and preparation method thereof
  • Ropivacaine hydrochloride impurity and preparation method thereof
  • Ropivacaine hydrochloride impurity and preparation method thereof

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preparation example Construction

[0032] The present invention also provides a method for preparing impurity ropivacaine hydrochloride with the structure shown in formula I, said method comprising the steps of: performing Vilsmeier-Haack reaction on the compound shown in formula II;

[0033]

Embodiment 1

[0035] A kind of preparation method of ropivacaine hydrochloride impurity as the embodiment of the present invention, described method comprises steps:

[0036] (1) Add 20ml dimethylformamide (DMF) and 10.2g (0.085mol) thionyl chloride in the reaction flask, add N-(2,6-dimethylphenyl) piperidine-2-carboxamide ( 10.0g, 0.043mol) of DMF solution 20ml, stirred until the end of the reaction, and determined the end point of the reaction by spot plate method;

[0037] (2) add water to the reaction system after step (1) to quench, adjust pH=14 with sodium hydroxide solution, add chloroform to extract;

[0038] (3) The organic phases were combined, spin-dried, concentrated to dryness after passing through the column to obtain 4.6 g of off-white solid powder with a purity of 98.9%.

[0039] Carry out NMR identification to the product, the result is: 1 H-NMR (CDCl 3 , 400MHz): δ1.4-1.8(6H,m), 2.20(6H,s), 3.4-3.6(2H,m), 5.2(1H,d), 7.0(3H,m), 7.4(1H,s ), 8.2 (1H, s); the product is de...

Embodiment 2

[0043] A kind of preparation method of ropivacaine hydrochloride impurity as the embodiment of the present invention, described method comprises steps:

[0044] (1) Add 20ml dimethylformamide (DMF) and 10.2g (0.085mol) thionyl chloride in the reaction flask, add N-(2,6-dimethylphenyl) piperidine-2-carboxamide ( 10.0g, 0.043mol), stirred until the end of the reaction;

[0045] (2) add water to the reaction system after step (1) to quench, adjust pH=13 with sodium hydroxide solution, add ethyl acetate for extraction;

[0046] (3) The organic phases were combined, spin-dried, dissolved by adding 25ml of methyl isobutyl ketone, cooled to 10-20°C and crystallized to obtain 4.8g of off-white solid powder.

[0047] Carry out NMR identification to the product, the result is:1 H-NMR (CDCl 3 , 400MHz): δ1.4-1.8(6H,m), 2.20(6H,s), 3.4-3.6(2H,m), 5.2(1H,d), 7.0(3H,m), 7.4(1H,s ), 8.2 (1H, s); the product is detected by liquid phase mass spectrometry, and the result is m / z: 261.2 [M+H],...

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Abstract

The invention provides a ropivacaine hydrochloride impurity and a preparation method thereof. The structural formula of the ropivacaine hydrochloride impurity is shown as a formula I, the ropivacainehydrochloride impurity disclosed by the invention is a new compound discovered by an inventor in a research process; the ropivacaine hydrochloride impurity has important significance in quality control in the ropivacaine hydrochloride synthesis process, and the inventor finds that the ropivacaine hydrochloride impurity with the structural formula shown in the formula I has excellent anesthetic performance through research and can be used for a new anesthetic drug. The method is simple to operate, the preparation method has the advantages of simple operation, mild conditions, realization of thereaction generation of the ropivacaine hydrochloride impurity only by mixing the reaction raw materials, no temperature control, low cost, no side reaction, high purity and high yield of the ropivacaine hydrochloride impurity prepared through the reaction, and facilitation of the reduction of the quality control analysis cost of ropivacaine hydrochloride.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a ropivacaine hydrochloride impurity and a preparation method thereof. Background technique [0002] Ropivacaine hydrochloride is an amide local anesthetic, a long-acting amide local anesthetic developed by Astra, Sweden, mainly used for surgical anesthesia and epidural anesthesia. Ropivacaine hydrochloride has dual effects of anesthesia and analgesia. Compared with amide local anesthetics such as bupivacaine, the drug has a longer drug action time and is less toxic to the heart. [0003] The impurities that may be produced during the production and storage of ropivacaine hydrochloride not only affect the purity of ropivacaine hydrochloride, but also affect the efficacy of the drug and may lead to toxic and side effects. Therefore, the research on the impurity of ropivacaine hydrochloride is of great significance. Contents of the invention [0004] The object of the present...

Claims

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Application Information

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IPC IPC(8): C07D211/60
CPCC07D211/60
Inventor 陈海龙柯海媚柳文俊李闫飞鞠云峰谭敏清
Owner GUANGDONG JIABO PHARM CO LTD
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