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N,N'-biacetylcysteine-diarginine salt isomer and its uses

A technology of diacetylcystine diarginine salt and isomer, which is applied in the field of arginine salt and can solve the problems of enhancing glutathione S-transferase activity and the like

Inactive Publication Date: 2008-01-09
吴锡铭
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, studies have shown that the pharmacological effects of N-acetylcysteine ​​are very diverse and cannot be completely replaced by its metabolite L-cystine. For example, N-acetylcysteine ​​molecules have direct anti-free radical effects, It also has the effect of enhancing the activity of glutathione S transferase (Moldeus P & Cotgreave IA. Meth. Enzymol. 234: 482-492, 1994); studies have shown that N-acetyl cysteine ​​has metal ion chelation, completely It is caused by the molecule itself and has nothing to do with the metabolites (Banner W Jr.et alToxicol.Appl.Pharmacol.83:142-147, 1986)

Method used

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  • N,N'-biacetylcysteine-diarginine salt isomer and its uses
  • N,N'-biacetylcysteine-diarginine salt isomer and its uses
  • N,N'-biacetylcysteine-diarginine salt isomer and its uses

Examples

Experimental program
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Effect test

Embodiment 1

[0048] Example 1 N, N'-diacetyl-L-cystine-L, the synthesis of L-diarginine salt

[0049] Put 672g of potassium hydroxide into a 5L reaction bottle, add 2400ml of water to dissolve it into concentrated lye, when the temperature drops to room temperature (20-30°C), add 360g of L-cystine, stir and dissolve, and cool to below 0°C. Slowly add acetic anhydride dropwise under cooling with an external ice-water bath, and control the internal temperature not to exceed 5°C. After the addition, continue to insulate and stir for 30 minutes, and place it for 3 hours. Add concentrated hydrochloric acid dropwise to adjust the pH to 2-3. Aqueous solution of acetylcystine.

[0050] The aqueous solution of acetylcystine was distilled under reduced pressure (external temperature 80°C), concentrated to a viscous state, extracted and filtered three times with acetone-water (90:10) to remove most of the inorganic salts. The extract was distilled off under reduced pressure to remove acetone, conc...

Embodiment 2

[0060] Example 2 N, N'-diacetyl-D-cystine-L, the synthesis of L-diarginine salt

[0061] Put 670g of potassium hydroxide into a 5L reaction bottle, add 2400ml of water to dissolve it into a concentrated lye, and when it cools down to room temperature (20-30°C), add 360g of D-cystine in batches, stir and dissolve, and cool to below 0°C. Slowly add acetic anhydride dropwise under cooling with an external ice-water bath, and control the internal temperature not to exceed 5°C. After the addition, continue to insulate and stir for 30 minutes, and place it for 3 hours. Add concentrated hydrochloric acid dropwise to adjust the pH to 2-3. Aqueous solution of acetylcystine.

[0062] The aqueous solution of acetylcystine was distilled under reduced pressure (external temperature 80°C), concentrated to a viscous state, extracted and filtered three times with acetone-water (90:10) to remove most of the inorganic salts. The extract was distilled off under reduced pressure to remove acet...

Embodiment 3

[0065] Example 3 N, N'-diacetyl-L-cystine-D, the synthesis of D-diarginine salt

[0066] Put 675g of potassium hydroxide into a 5L reaction bottle, add 2400ml of water to dissolve it into a concentrated lye, and when it cools down to room temperature (20-30°C), add 360g of L-cystine, stir and dissolve, and cool to below 0°C. Slowly add acetic anhydride dropwise under cooling with an external ice-water bath, and control the internal temperature not to exceed 5°C. After the addition, continue to insulate and stir for 30 minutes, and place it for 3 hours. Add concentrated hydrochloric acid dropwise to adjust the pH to 2-3. Aqueous solution of acetylcystine.

[0067] The aqueous solution of acetylcystine was distilled under reduced pressure (external temperature 80°C), concentrated to a viscous state, extracted and filtered three times with acetone-water (90:10) to remove most of the inorganic salts. The extract was distilled off under reduced pressure to remove acetone, concen...

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Abstract

The invention relates to the constitutional isomers of N,N'-diacetyl cystine diarginine salts, their preparing process and medical use, and the pharmaceutical composition using the preferred constitutional isomers as the reactive components. Selecting constitutional isomers whose molecule has L type or internal compensation type cystine, and the arginine in the molecule has a constitution containing at least one L type arginine. The selected isomers can be used for preparing medicament for antineoplastic and treating immunodeficiency diseases, self immune diseases, infection diseases or hepatic diseases.

Description

technical field [0001] The present invention relates to N, N'-diacetylcystine arginine salt with immunomodulatory activity, a pharmaceutical composition containing N, N'-diacetylcystine di-arginine salt configuration isomer, Its preparation method and medicinal use. technical background [0002] N-Acetylcysteine ​​is a well-known sulfhydryl-containing amino acid derivative with various biological activities, e.g. as a mucolytic agent for respiratory diseases; in reduced glutathione reduction and oxidative stress It has also been studied and applied; it can still be used for acute liver failure caused by drug poisoning. Clinical studies in recent years have proved that it also has good curative effect on liver failure caused by various hepatitis viruses. The pharmacological mechanisms of N-acetylcysteine ​​are diverse, including strong antioxidant effects, stimulation of glutathione synthesis, effects on nitric oxide production and its synthetase activity, and so on. [00...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C323/59C07C319/20A61K31/198A61P37/02A61P35/00A61P31/00A61P1/16
Inventor 吴锡铭杨玲夏春光张来芳张喜全
Owner 吴锡铭
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