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Purification and refining method of R-lipoic acid choline ester halide

A lipoic acid choline, purification and refining technology, applied in the direction of organic chemistry, etc., can solve the problem of not giving R-lipoic acid choline ester halide, etc., and achieve the effect of improving purity and quality

Inactive Publication Date: 2018-09-28
SUZHOU FUSHILAI PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] However, the above-mentioned documents do not provide the technical inspiration for purifying and refining the R-lipoic acid choline ester halide so as to improve the purity and ensure the quality. The technical scheme to be introduced below is produced under this background:

Method used

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  • Purification and refining method of R-lipoic acid choline ester halide
  • Purification and refining method of R-lipoic acid choline ester halide
  • Purification and refining method of R-lipoic acid choline ester halide

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Experimental program
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Effect test

Embodiment 1

[0023] Add R-lipoic acid-2-chloroethyl ester (12.0g) and toluene (200mL) into the reaction flask, stir to dissolve, cool in an ice bath, add 16.9M trimethylamine aqueous solution (7.5mL) dropwise, and react the reaction mixture at 90°C for 18h . The organic solvent was removed by rotary evaporation under reduced pressure, extracted with ethyl acetate, the extract was evaporated to dryness under reduced pressure, the residue (16g) was dissolved in chloroform (40mL), cooled to room temperature, silica gel (32g) was added, and stirred at 35°C , filtered, the filtrate was rotary evaporated to 25mL under reduced pressure, cooled to 0°C for crystallization for 12h, filtered, and dried to obtain R-lipoic acid choline ester chloride, light yellow solid (12.3g), yield 84%, R-sulfur The octanoic acid choline chloride is greater than 99.5%, and the R-lipoic acid-2-chloroethyl ester raw material content is less than 0.05%.

Embodiment 2

[0025] Add R-lipoic acid-2-bromoethyl (15.5g) and acetonitrile (200mL) into the reaction flask, stir to dissolve, cool in an ice bath, add 16.9M trimethylamine aqueous solution (6.5mL) dropwise, and react the reaction mixture at 60°C for 24h . The organic solvent was removed by rotary evaporation under reduced pressure, extracted with ethyl acetate, the extract was evaporated to dryness under reduced pressure, the residue (18g) was dissolved in toluene (40mL), cooled to room temperature, silica gel (50g) was added, and stirred at 40°C , filtered, the filtrate was rotary evaporated to 25mL under reduced pressure, cooled to 1°C for crystallization for 16h, filtered, and dried to obtain R-lipoic acid choline ester bromide, a light yellow solid (14.3g), yield 78%, R-sulfur The octanoic acid choline chloride is greater than 99.5%, and the raw material content of R-lipoic acid-2-bromoethyl is less than 0.05%.

Embodiment 3

[0027] Add R-lipoic acid-2-iodoethyl ester (23.0g) and N,N-dimethylformamide (250mL) into the reaction flask, stir to dissolve, cool in an ice bath, add dropwise 16.9M trimethylamine aqueous solution (6.0mL) , The reaction mixture was reacted at 120°C for 12h. The organic solvent was removed by rotary evaporation under reduced pressure, extracted with ethyl acetate, the extract was evaporated to dryness under reduced pressure, the residue (29g) was dissolved in ethyl acetate (65mL), cooled to room temperature, silica gel (33g) was added, and 34°C Stir evenly, filter, the filtrate is 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 iodide, light yellow solid (20.0g), yield 75%, R -Lipoic acid choline ester bromide is greater than 99.5%, R-lipoic acid-2-iodoethyl ester raw material content is less than 0.05%.

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Abstract

The invention provides a purification and refining method of R-lipoic acid choline ester halide and belongs to the technical field of medicine chemistry. The method includes the steps of adding R-lipoic acid-2-R-dissolving lipoic acid choline ester halide crude product into solvent, dissolving completely, adding silica gel into solution, stirring at 30-40 DEG C; and filtering to obtain filtrate, recrystallizing the obtained filtrate to obtain R- lipoic acid choline ester halide pure product, wherein R-lipoic acid-2- haloethyl ester raw material content is less than 0.05%, and R- lipoic acid choline ester halide is more than 99.5%. The purity of R-lipoic acid choline ester halide is improved, which provides a reliable guarantee for improving the quality of the R-lipoic acid 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 purifying 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 devel...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D339/04
CPCC07D339/04
Inventor 莫国宁
Owner SUZHOU FUSHILAI PHARMA CO LTD
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