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Preparation of balsalazide disodium

A technology of balsalazide sodium and balsalazide, applied in the field of medicine, can solve the problems of inability to meet medicinal requirements, affect product quality, low product purity, etc., solve the problem of salt-forming reaction selectivity, improve product purity, and improve product quality. high purity effect

Inactive Publication Date: 2009-08-12
SHANXI ZHENDONG ANTE BIOPHARMACEUTICAL CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The problem with this method is that the crude product of balsalazide is not purified, resulting in low purity of the final product, which cannot meet the requirements of medicine
At present, in the synthesis method of balsalazide sodium, the catalytic hydrogenation steps are all carried out in ethanol, which requires the use of a large amount of organic solvent ethanol, which is easy to affect the environment, and the cost is high
In addition, studies have found that due to the strong alkalinity of sodium hydroxide, the phenolic hydroxyl groups in the structure of balsalazide are often formed into salts during the process of salt formation, thereby affecting product quality.

Method used

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  • Preparation of balsalazide disodium
  • Preparation of balsalazide disodium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] 1) Synthesis of balsalazide

[0029] Add 23.19g of β-alanine and 21.2g of sodium hydroxide into 160ml of water, stir and dissolve, and cool to 5°C. Grind 40g of p-nitrobenzoyl chloride finely, add to the above aqueous solution in batches, stir for reaction, maintain the reaction temperature at 5°C, and stir for 3 hours at this temperature after the addition is complete. Add 2.4g of 5% Pd-C, and add hydrogen at room temperature and pressure under stirring until no hydrogen is absorbed. Add 68.4ml of concentrated hydrochloric acid to the reaction solution, stir for 20 minutes, then add 284ml of water, stir for 10 minutes, and cool to -5°C in an ice-salt bath. At the same time, 8.6g of sodium nitrite was added to 57ml of water to dissolve and cooled to 0°C. The sodium nitrite aqueous solution was added dropwise to the aqueous solution cooled by the ice-salt bath. The reaction was incubated at 0°C for 1 hour to obtain a diazonium salt solution.

[0030] Add 10.1g of sod...

Embodiment 2

[0040] Balsalazide was prepared according to the method described in Example 1, except that 70% ethanol aqueous solution was used instead of 70% acetic acid aqueous solution for recrystallization. The yield was 69.3%, and the HPLC purity was 94.1%.

Embodiment 3

[0042] Balsalazide was prepared according to the method described in Example 1, except that 50% acetic acid aqueous solution was used for recrystallization. The yield was 67.2%, and the HPLC purity was 99.6%.

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PUM

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Abstract

The invention provides a balsalazide sodium preparing method comprising acylation reaction, catalytic hydrogenation reaction and diazotization reaction, which are sequentially implemented to prepare balsalazide. The catalytic hydrogenation reaction is carried out by taking water as the solvent; and the balsalazide is prepared into the balsalazide sodium after salt-forming reaction. The preparing method has the advantages of easily obtained raw materials, mild reaction conditions, simple and easy operation, short synthesizing route, high yield rate, high product purity, applicability for industrial production, etc.

Description

technical field [0001] The invention relates to the field of medicine, in particular, the invention relates to a preparation method of balsalazide sodium. Background technique [0002] (E)-5-[[4-(2-carboxyethyl)carbamoyl]phenylazo]salicylic acid disodium salt dihydrate (sodium balsalazide), the molecular formula is C 17 h 13 N 3 Na 2 o 6 2H 2 O, the English name is DisodiumBalsalazide, and the structural formula (I) is as follows: [0003] [0004] Balsalazide sodium is a 5-ASA prodrug. After it reaches the colon after oral administration, under the action of intestinal bacterial enzymes, the azo bond is broken to release 5-ASA to produce curative effect. This product can be used as a first-line drug for the treatment of mild to moderate active ulcerative colitis, and eight weeks of treatment can effectively improve the relevant symptoms of patients with active ulcerative colitis. [0005] British Patent GB 2080796 (Reference 1) in 1982 discloses a preparation meth...

Claims

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Application Information

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IPC IPC(8): C07C245/08
Inventor 王绍杰姚娟娟杨福安吴月侠穆清苏
Owner SHANXI ZHENDONG ANTE BIOPHARMACEUTICAL CO LTD