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Levamisole organic acid salt, synthetic method for levamisole organic acid salt and medicinal composition of levamisole organic acid salt

A technology of levamisole and organic acid salts, which is applied in the field of medicine, can solve the problems of reducing the stability of finished products, low bioavailability, and adding related substances, and achieve the effects of improving thermal stability, high bioavailability, and reducing irritation

Inactive Publication Date: 2012-09-19
CHONGQING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Though these medicines have good immunoenhancing effect, they have weak point, and wherein the dextrorotatory side reaction of tetramisole is bigger, so the curative effect of this medicine is not as good as similar; A lot of inconvenience, and prone to easy structure, thereby increasing the related substances of this product, making the content inaccurate, so that the therapeutic effect may not be achieved; both levamisole hydrochloride and levamisole phosphate are inorganic salts, and there are chloride ions and phosphate radicals Ions, which increase the instability of the drug and reduce the stability of the finished product, and the inorganic strong salt has a certain stimulating effect on the human body, poor absorption in the body, and low bioavailability

Method used

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  • Levamisole organic acid salt, synthetic method for levamisole organic acid salt and medicinal composition of levamisole organic acid salt
  • Levamisole organic acid salt, synthetic method for levamisole organic acid salt and medicinal composition of levamisole organic acid salt
  • Levamisole organic acid salt, synthetic method for levamisole organic acid salt and medicinal composition of levamisole organic acid salt

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Example 1: Add 48 g of levamisole hydrochloride (II) and 200 ml of distilled water into the reaction flask, stir to dissolve, add 200 ml of 1 mol / L NaOH aqueous solution dropwise in an ice bath, stir until the solution pH=7~12, and heat in a water bath to 40°C and continue stirring for 30 minutes. Filter, wash the filter cake with distilled water until neutral, and dry under reduced pressure to obtain levamisole free base (Ⅲ). The filtrate was extracted three times with dichloromethane, 160ml for the first time, and 120ml for the second and third times. The extracts were combined, and distilled water was added to the extracts, stirred and cleaned, left to separate, and washed repeatedly until the lotion was weakly alkaline. Dry with anhydrous calcium chloride for 6h and filter. Dichloromethane was distilled off under reduced pressure to obtain levamisole free base (Ⅲ) as a white solid, which was combined with levamisole free base.

[0073] In the dry reaction bottle, ...

Embodiment 2

[0074] Example 2: Add 48g of levamisole hydrochloride (II) and 200ml of distilled water into the reaction bottle, stir to dissolve, add dropwise 360ml of 1mol / L NaOH aqueous solution under the condition of ice bath, stir until the solution pH=7~12, and heat in a water bath To 40°C, continue stirring for 5.5h. Filter, wash the filter cake with distilled water until neutral, and dry under reduced pressure to obtain levamisole free base (Ⅲ). The filtrate was extracted three times with ether, 240ml for the first time, 90ml for the second and third times, combined the extracts, then added distilled water to the extracts, stirred and cleaned, left to separate, and repeated cleaning until the lotion was weakly alkaline. Calcium chloride water dried for 6h, filtered. Diethyl ether was distilled off under reduced pressure to obtain levamisole free base (Ⅲ) as a white solid, which was combined with levamisole free base.

[0075] In the dry reaction bottle, add 30ml of anhydrous methan...

Embodiment 3

[0076] Example 3: Add 48g of levamisole hydrochloride (II) and 200ml of distilled water into the reaction flask, stir to dissolve, add dropwise 400ml of 1mol / L NaOH aqueous solution under the condition of ice bath, stir until the solution pH=7~12, and heat in a water bath To 25°C, continue stirring for 3h. Filter, wash the filter cake with distilled water until neutral, and dry under reduced pressure to obtain levamisole free base (Ⅲ). The filtrate was extracted three times with a mixed solvent of dichloromethane and diethyl ether (1:1), 320ml for the first time, 160ml for the second and third times respectively, combined the extracts, then added distilled water to the extracts, stirred and cleaned, stood to separate, and repeated Wash until the lotion is weakly alkaline, dry with anhydrous calcium chloride for 12 hours, and filter. The solvent was evaporated under reduced pressure to obtain levamisole free base (Ⅲ) as a white solid, and the levamisole free base was combined....

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Abstract

The invention relates to levamisole organic acid salt, a synthetic method for the levamisole organic acid salt and a medicinal composition of the levamisole organic acid salt. The levamisole organic acid salt is represented by a general formula (I). The synthetic method for the levamisole organic acid salt comprises the following steps of: dripping an aqueous solution of sodium hydroxide into levamisole hydrochloride which is taken as an initial raw material, reacting for a period of time, extracting by using an organic solvent, and drying and concentrating to obtain white solid levamisole free alkali; and dissolving the levamisole free alkali into a reaction solvent, adding organic acid at certain temperature, reacting under stirring, filtering, freezing a filtrate till the temperature of 2 to 10 DEG C, slowly dripping a precipitation solvent under stirring, precipitating crystals, filtering, washing, and drying to obtain the levamisole organic acid salt. The method is simple and quick and is short in production cycle, low in cost and high in yield, and reaction conditions are mild. The levamisole organic acid salt has high water solubility, stability and bioavailability. The medicinal composition contains a therapeutically effective amount of levamisole organic acid salt shown as the formula (I) and a pharmaceutically acceptable carrier.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a levamisole organic acid salt, a synthesis method thereof and a pharmaceutical composition using the levamisole organic acid salt as an active ingredient. Background technique [0002] The body's immune system is mainly responsible for the defense and elimination of foreign bodies and aging mutant cells in the body. Reduced immune function of the body can lead to infection, tumor or immunodeficiency diseases. For infections, tumors and immunodeficiency diseases caused by low immune function, specific or non-specific immune enhancers can be used for treatment, which is conducive to strengthening the immune system function of the body and alleviating immune dysfunction caused by environmental stress , beneficial for the prevention and treatment of infectious and conditional diseases. [0003] Levamisole (LMS), also known as Levamisole or Levamisole, its chemical name is (S)-(-)-6-phenyl-...

Claims

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Application Information

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IPC IPC(8): C07D513/04C07J63/00C07H15/06C07H1/00A61K31/429A61K31/56A61K31/455A61K31/7032A61P37/04
Inventor 王建华杨毅
Owner CHONGQING UNIV
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