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Lipoic acid preparation method and application of lipoic acid in preparation of drug for treating oligospermia

A technology of lipoic acid and lipoic acid ethyl ester, which can be used in pharmaceutical combinations, medical preparations containing active ingredients, pharmaceutical formulations, etc., can solve problems such as the meaninglessness of impurity B control, patient harm, and restricting the application of lipoic acid, and achieve easy access. Industrial production, simple method, and the effect of improving sperm motility

Inactive Publication Date: 2019-04-05
GRAND LIFE SCI (LIAONING) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since impurity B cannot be detected in liquid chromatography, this purity investigation is meaningless for the control of impurity B
Lipoic acid is widely used clinically, including for the treatment of oligospermia, but long-term medication is required, and the daily dose is 600 mg. If the impurity B in lipoic acid is not strictly controlled, the accumulation of impurities caused by long-term medication will inevitably cause harm to patients , limiting the application of lipoic acid in the treatment of oligospermia

Method used

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  • Lipoic acid preparation method and application of lipoic acid in preparation of drug for treating oligospermia
  • Lipoic acid preparation method and application of lipoic acid in preparation of drug for treating oligospermia
  • Lipoic acid preparation method and application of lipoic acid in preparation of drug for treating oligospermia

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Into the reaction flask, 24.1 g of ethyl 6,8-dichlorooctanoate, 3.8 g of sulfur powder, 192 mL of isopropanol and 48 mL of propanol were sequentially put into the reaction flask, stirred, protected by nitrogen, protected from light, and heated to reflux. After refluxing, start to add sodium sulfide solution (30g sodium sulfide nonahydrate dissolved in a mixed solvent of 80mL water, 32mL isopropanol and 8mL propanol). The addition time is 2.5h. After the addition is complete, add the aqueous ammonium bisulfite solution (29.7g ammonium bisulfite dissolved in 75mL water), stirred at 70°C for 1h, cooled to 35°C, added 300mL water and 200mL cyclohexane, adjusted the pH of the aqueous phase to 1 with 10wt% hydrochloric acid, stirred for 15min, and separated layers , To obtain a cyclohexane solution of ethyl lipoic acid.

[0063] Add the cyclohexane solution of ethyl lipoic acid ethyl ester, 400 mL of water and 6 g of sodium hydroxide into the reaction flask, protect from light a...

Embodiment 2

[0065] Into the reaction flask, 24.1 g of ethyl 6,8-dichlorooctanoate, 6.4 g of sulfur powder, 48 mL of methanol and 48 mL of isopropanol were sequentially put into the reaction flask, stirred, protected by nitrogen, protected from light, and heated to reflux. After refluxing, start to add sodium sulfide solution (36g sodium sulfide nonahydrate dissolved in 80mL water, 20mL isopropanol and 20mL methanol), the dripping time is 1.5h, after the addition is complete, add potassium sulfite aqueous solution (31.7g potassium sulfite Dissolved in 75mL water), stirred at 80°C for 2h, then cooled to 35°C, added 300mL of water and 200mL of cyclohexane, adjusted the pH of the aqueous phase to 1 with 10% hydrochloric acid, stirred for 15min, and separated layers to obtain ethyl lipoic acid ethyl ester Cyclohexane solution.

[0066] Add a cyclohexane solution of ethyl lipoic acid ethyl ester, 800 mL of water and 16 g of sodium hydroxide into the reaction flask, protect from light and protect w...

Embodiment 3

[0069] Into the reaction flask, 24.1 g of ethyl 6,8-dichlorooctanoate, 5.1 g of sulfur powder, and 120 mL of ethanol were sequentially put into the reaction flask, stirred, protected by nitrogen, protected from light, and heated to reflux. After refluxing, start to add sodium sulfide solution (24g sodium sulfide nonahydrate dissolved in 80mL water, 40mL ethanol), the dripping time is 2h, after the addition is complete, add sodium bisulfite aqueous solution (10.4g sodium bisulfite dissolved in 75mL After stirring for 0.5h at 60℃, the temperature was lowered to 35℃, 300mL of water and 200mL of cyclohexane were added, and the pH of the aqueous phase was adjusted to 1 with 10wt% hydrochloric acid. After stirring for 15min, the layers were separated to obtain the cyclohexane of ethyl lipoic acid. Hexane solution.

[0070] Add a cyclohexane solution of ethyl lipoic acid, 100 mL of water, and 11.2 g of potassium hydroxide into the reaction flask, protect from light and protect with nitr...

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Abstract

The invention provides a lipoic acid preparation method. The lipoic acid preparation method is characterized by comprising the following steps: (1) carrying out cyclization reaction on ethyl 6,8-dichloro caprylate to prepare lipoic acid ethyl ester; (2) converting 6,8-epitrithio-octanoic acid in the lipoic acid ethyl ester obtained in step (1) into lipoic acid ethyl ester by using sulfite; (3) hydrolyzing the lipoic acid ethyl ester under the effect of alkali to prepare a lipoic acid crude product; and (4) and carrying out recrystallization and drying on the lipoic acid crude product to prepare high-purity lipoic acid, wherein in step (4), recrystallization comprises carrying out heat dissolving on the lipoic acid crude product, filtering a hot lipoic acid solution through an adsorption layer, and crystallizing and filtering filtrate. By the method, known impurities B in the lipoic acid are controlled, the method is simple, and is easy to operate, the purity of the obtained product ishigh, the high-purity lipoic acid can be obtained by only one-time refining, and industrial production is facilitated. In addition, by the lipoic acid prepared by the method, oligospermia can be treated, the density of sperms is increased, and the activity of the sperms is improved.

Description

Technical field [0001] The present invention relates to the technical field of drug treatment and synthesis, in particular to a method for preparing lipoic acid, and the application of the lipoic acid prepared by the method in preparing a medicine for treating oligospermia. Background technique [0002] Lipoic acid is a natural cofactor of mitochondrial dehydrogenase and a vitamin 2- ·, Other free radicals and active oxygen other than ROO· play an anti-oxidant effect. Moreover, lipoic acid can chelate iron ions, copper ions and other transition metal elements such as Mn 2+ , Cd 2+ , Zn 2+ It can reduce the production of OH·, block lipid peroxidation, and even detoxify heavy metal ion poisoning. Together with the reduced form of dihydrolipoic acid (DHLA), it is known as the "universal resistance" Oxidant". [0003] In the prior art, the synthesis method of lipoic acid has been reported in many literatures, Li Weimin et al. (Li Weimin, Guan Xiaowei, Gu Zhenggui, Gu Meijuan, Research...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D339/04A61K31/385A61P15/08
CPCA61K31/385C07D339/04
Inventor 陈阳张良赵凯华葛琳邸伟庆薛雁李萍王宏英薛百忠
Owner GRAND LIFE SCI (LIAONING) CO LTD
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