S-(carboxymethyl)-cysteine pharmaceutical compound and preparation method and usage thereof

A pharmaceutical compound, cysteine ​​technology, applied in the preparation of organic compounds, drug combinations, chemical instruments and methods, etc., can solve problems such as damage to gastrointestinal mucosa, bleeding, ulcers and even perforation, and irritating effects on the digestive tract

Active Publication Date: 2013-01-09
GUANGZHOU BAIYUNSHAN PHARMA HLDG CO LTD BAIYUNSHAN PHARMA GENERAL FACTORY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] As an expectorant drug, carbocisteine ​​is widely produced and used in my country, but there are two carboxyl groups in the structure of carbocisteine, which is acidic, which makes the drug irritating to the digestive tract and can cause gastr

Method used

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  • S-(carboxymethyl)-cysteine pharmaceutical compound and preparation method and usage thereof
  • S-(carboxymethyl)-cysteine pharmaceutical compound and preparation method and usage thereof
  • S-(carboxymethyl)-cysteine pharmaceutical compound and preparation method and usage thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0089] Preparation of S-(carboxymethyl)-D-cysteine ​​arginine salt tetrahydrate crystalline compound:

[0090] At room temperature, add 20g of S-(carboxymethyl)-D-cysteine, 19.5g of arginine, and 50ml of distilled water into a three-neck flask equipped with a stirring device, heat the water bath to 50°C, keep stirring to make the reaction solution After dissolving and clearing, add 100ml of n-butanol dropwise to the reaction solution. The dropping speed is slightly faster at the beginning, and slow down when white crystals are precipitated. The filter cake was washed with n-butanol, sucked dry, and dried to obtain 37.5 g of white S-(carboxymethyl)-D-cysteine ​​arginine salt tetrahydrate crystals, with a yield of about 79.0%. The moisture content was 16.95%, and the element analysis results were C 31.12%, S 7.54%, N 16.86%, and O 37.66%.

Embodiment 2

[0092] Preparation of S-(carboxymethyl)-D-cysteine ​​arginine salt pentahydrate crystalline compound:

[0093] At room temperature, add 25g of S-(carboxymethyl)-D-cysteine, 24.5g of arginine, and 20ml of distilled water into a three-neck flask equipped with a stirring device, heat the water bath to 50°C, keep stirring to make the reaction solution After dissolving, add dropwise the mixed solution of 50ml isopropanol and 50ml tetrahydrofuran therein. At the beginning, the drop rate is slightly faster, and when white crystals are precipitated, the drop rate is slowed down. Wash the filter cake with a small amount of the above-mentioned mixed solution, drain it, and dry it to obtain 54.8 g of white S-(carboxymethyl)-D-cysteine ​​arginine salt pentahydrate crystals, with a yield of about 88.6%. The moisture determination result is 20.1%, and the elemental analysis results are C 29.73%, S 7.24%, N 15.86%, O 39.61%.

Embodiment 3

[0095] Preparation of S-(carboxymethyl)-L-cysteine ​​arginine salt trihydrate crystalline compound:

[0096] At room temperature, add 20g of S-(carboxymethyl)-L-cysteine, 19.5g of arginine, and 50ml of distilled water into a three-neck flask equipped with a stirring device, heat the water bath to 50°C, keep stirring to make the reaction solution After dissolving and clearing, add 300ml of ethanol dropwise to the reaction liquid. The dropping speed is slightly faster at the beginning, and slow down when white crystals are precipitated. After the ethanol is added dropwise, grow crystals at 20°C, filter with suction, and wash the filter cake with a small amount of ethanol. , drained, and dried to obtain 42.7 g of white S-(carboxymethyl)-L-cysteine ​​arginine salt trihydrate crystals, with a yield of about 93.9%. The moisture content was 13.7%, and the element analysis results were C 32.42%, S 7.96%, N 17.23%, and O 35.38%.

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Abstract

The invention relates to an S-(carboxymethyl)-cysteine pharmaceutical compound and a preparation method and the usage of the compound; the structural formula of the compound is shown by (I); and the compound is especially applied to the preparation of medicines for eliminating phlegm as well as medicines for preventing and treating respiratory system diseases such as chronic obstructive pulmonary diseases (COPD) and the like. After the compound is adopted, the COPD model rat airway resistance is remarkably reduced, the generation of oxide is reduced, the antioxidant level is increased, and the damage of oxide, inflammatory mediator and the like to the lung can be relieved.

Description

technical field [0001] The invention belongs to the field of chemical pharmacy, in particular, the invention relates to a class of S-(carboxymethyl)-cysteine ​​pharmaceutical compounds and their preparation method and application. Background technique [0002] Carbocisteine, whose chemical name is S-(carboxymethyl)-L-cysteine ​​(carbocisteine, carboxymethylcysteine, CMC), was first developed and applied clinically by the French Joullie company in 1961. It is a mucolytic drug, It can affect the secretion of bronchial glands, increase the secretion of low-viscosity salivary mucin, reduce the production of high-viscosity fucoidal mucin, and directly act on the disulfide bond of mucin to crack mucin molecules and reduce sputum. Viscous fluid, easy to spit out; can improve mucociliary clearance rate; reduce airway hyperresponsiveness. After CMC enters the body, it is easy to remove the carboxymethyl group to form cysteine, and the sulfhydryl group contained in it can interact wi...

Claims

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Application Information

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IPC IPC(8): C07C323/58C07C319/28A61K31/198A61P11/10A61P11/00
Inventor 钟南山陈矛朱少璇郑劲平万平王玮莫红缨廖维胡海容余瑜傅祥麟冯金黄冰娥张琳
Owner GUANGZHOU BAIYUNSHAN PHARMA HLDG CO LTD BAIYUNSHAN PHARMA GENERAL FACTORY
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