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Refining method of R-thioctic choline ester halide

A kind of technology of lipoic acid choline and refining method, applied in the refining field of R-lipoic acid choline ester halide, can solve the problems such as not giving R-lipoic acid choline ester halide, etc., to improve purity and quality Effect

Inactive Publication Date: 2018-11-16
SUZHOU FUSHILAI PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] But above-mentioned literature does not provide the technical enlightenment that R-lipoic acid choline ester halide is refined so as to improve purity, guarantee quality, and the technical scheme that will introduce below is exactly produced under this background:

Method used

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  • Refining method of R-thioctic choline ester halide
  • Refining method of R-thioctic choline ester halide
  • Refining method of R-thioctic choline ester halide

Examples

Experimental program
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Effect test

Embodiment 1

[0023] Add R-lipoic acid (10.0g) and chloroform (120mL) into the reaction flask, stir to dissolve, add N,N'-dicyclohexylcarbodiimide (12.0g) and 4-dimethylaminopyridine (1.2g) , cooled in an ice bath, choline chloride (15.2 g) was added, and the reaction mixture was reacted at 35° C. for 18 h. Filtrate, extract the filter cake with ethyl acetate, combine the extracts and filtrate, and rotary evaporate to dryness under reduced pressure. The residue (31g) was dissolved in chloroform (80mL), cooled to room temperature, added silica gel (60g), and stirred at 35°C until uniform. Filtration, the filtrate was rotary evaporated to 30mL under reduced pressure, cooled to 0°C and crystallized for 12h, filtered, and dried to obtain R-lipoic acid choline ester chloride, a light yellow solid (14.1g), yield 89%, liquid phase detection, R-lipoic acid choline ester chloride is greater than 99.7%, and the raw material content of choline chloride is less than 0.1%.

Embodiment 2

[0025] Add R-lipoyl chloride (10.0g) and toluene (160mL) into the reaction flask, stir to dissolve, add N,N-diethylaniline (26.6g), cool in an ice bath, add choline chloride (18.6g), The reaction mixture was reacted at 20°C for 12h. Filtrate, extract the filter cake with ethyl acetate, combine the extracts with the filtrate, and rotary evaporate to dryness under reduced pressure. The residue (30g) is dissolved in toluene (100mL), cooled to room temperature, added with silica gel (85g), and stirred at 40°C. Filtration, the filtrate was rotary evaporated to 30mL under reduced pressure, cooled to 1°C and crystallized for 16h, filtered, and dried to obtain R-lipoic acid choline ester chloride, a light yellow solid (11.3g), yield 78%, liquid phase detection, R-lipoic acid choline ester chloride is greater than 99.7%, and the raw material content of choline chloride is less than 0.1%.

Embodiment 3

[0027] Add R-lipoic acid (10.0g) and ethyl acetate (150mL) into the reaction flask, stir to dissolve, add N,N'-carbonyldiimidazole (8.6g) and 2,6-lutidine (0.5g), After cooling in an ice bath, choline bromide (26.8 g) was added, and the reaction mixture was reacted at 20° C. for 24 h. Filtrate, extract the filter cake with ethyl acetate, combine the extracts and filtrate, and rotary evaporate to dryness under reduced pressure. The residue (29g) was dissolved in ethyl acetate (77mL), cooled to room temperature, added silica gel (32g), and stirred at 32°C Uniform, filtered, and the filtrate was rotary evaporated to 30mL under reduced pressure, cooled to 2°C and crystallized for 14h, filtered, and dried to obtain R-lipoic acid choline ester bromide, light yellow solid (15.4g), yield 85%, R- The lipoic acid choline ester bromide is greater than 99.7%, and the raw material content of choline bromide is less than 0.1%.

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Abstract

A refining method of R-thioctic choline ester halide belongs to the technical field of pharmaceutical chemistry and comprises the following steps: adding a R-thioctic choline ester halide crude product obtained by a reaction between R-lipoic acid or R-sulfur octanoyl chloride and choline halide into a solvent and completely dissolving to obtain a solution, adding silica gel into the solution, uniformly stirring at 30-40 DEG C, and filtering to obtain a filtrate; and recrystalizing the filtrate to obtain a R-thioctic choline ester halide pure product. The content of the choline halide raw material is less than 0.1%, and the content of R-thioctic choline ester halide is greater than 99.7%. By the refining method, purity of the R-thioctic choline ester halide is raised. The invention providesreliable guarantee for enhancing quality of an R-thioctic choline ester halide drug.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to a method for refining R-lipoic acid choline ester halide. Background technique [0002] Lipoic acid (α-Lipoic acid) is a biologically active natural product that was first isolated from pig liver by Reed in 1951. Lipoic acid contains a chiral center. Studies have shown that the two enantiomers of lipoic acid, the R-enantiomer has biological activity, while the S-enantiomer is basically inactive and non-toxic. Lipoic acid has been widely used in the field of clinical medicine in Europe and America, such as liver disease, senile dementia, cataract, heart disease, diabetes, AIDS, psoriasis, eczema, Parkinson's disease, rheumatism, heart disease, neurological disease, subacute necrosis It is known as "universal antioxidant" for the treatment of diseases such as encephalopathy, radiation injury, and heavy metal poisoning. With the in-depth research and develo...

Claims

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Application Information

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IPC IPC(8): C07D339/04
CPCC07D339/04
Inventor 莫国宁
Owner SUZHOU FUSHILAI PHARMA CO LTD
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