Method for synthesizing salazosulfapyridine using pyridazol as raw material

A technology of sulfasalazine and sulfasalazine, which is applied in the field of sulfasalazine, can solve the problems of less sources, unsatisfactory product purity, and difficult synthesis, and achieve the effects of high side reactions, large industrial production value, and guaranteed yield

Inactive Publication Date: 2016-03-02
苏州统华药品有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The starting material 4-(4-acetoxy group-3-carbonylmethoxyphenyl azo)-benzenesulfonyl chloride of this method is not commercially available at present and the compa

Method used

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  • Method for synthesizing salazosulfapyridine using pyridazol as raw material
  • Method for synthesizing salazosulfapyridine using pyridazol as raw material
  • Method for synthesizing salazosulfapyridine using pyridazol as raw material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Sulfapyridine and the hydrochloric acid that substance quantity is 1.5 (taking the substance quantity of sulfapyridine as 1) fully mix, form A reaction liquid; Fully mix with THF with a mass of 5 (the mass of sulfapyridine is 1) to form a B reaction solution. The A reaction solution and the B reaction solution were transported to the tubular reactor through a peristaltic pump at a feed rate of 42 mL / min, mixed through a Y-shaped tube, and then entered into the tubular reactor (the temperature in which was controlled at 0°C). After staying for 40s, the material is discharged. The diazonium salt intermediate was isolated using known methods and this was named A.

[0025] Put salicylic acid and partial sodium hydroxide (taking the amount of sulfapyridine as 1) in the reaction bottle. After the temperature was controlled to 5°C, the above-mentioned A was slowly started to be dropped into the above-mentioned reaction flask, and at the same time, the remaining sodium hydrox...

Embodiment 2

[0027] Sulfapyridine and hydrochloric acid with a substance quantity of 3 (calculated as 1 in the substance quantity of sulfapyridine) are fully mixed to form A reaction solution; Fully mix with THF with a mass of 10 (the mass of sulfapyridine is 1) to form a B reaction solution. The A reaction solution and the B reaction solution were transported to the tubular reactor through a peristaltic pump at a feed rate of 55 mL / min, mixed through a Y-shaped tube, and then entered into the tubular reactor (the temperature in which was controlled at 5°C). After staying for 15s, discharge the material. The diazonium salt intermediate was isolated using known methods and this was named A.

[0028] Put salicylic acid and partial sodium hydroxide (taking the amount of sulfapyridine as 1) in the reaction bottle. After the temperature was controlled to 10°C, the above-mentioned A was slowly started to be dropped into the above-mentioned reaction flask, and at the same time, the remaining so...

Embodiment 3

[0030] Sulfapyridine and the hydrochloric acid that substance quantity is 2.2 (taking the substance quantity of sulfapyridine as 1) fully mix, form A reaction liquid; Fully mix with THF with a mass of 7 (the mass of sulfapyridine is 1) to form a B reaction solution. The A reaction solution and the B reaction solution were transported to the tubular reactor through a peristaltic pump at a feed rate of 42 mL / min, mixed through a Y-shaped tube, and then entered into the tubular reactor (the temperature in which was controlled at 3°C). After staying for 40s, the material is discharged. The diazonium salt intermediate was isolated using known methods and this was named A.

[0031] Put salicylic acid and partial sodium hydroxide (taking the amount of sulfapyridine as 1) in the reaction bottle. After the temperature was controlled to 7°C, the above-mentioned A was slowly started to be dropped into the above-mentioned reaction flask, and at the same time, the remaining sodium hydrox...

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Abstract

The present invention discloses a method for synthesizing salazosulfapyridine. The synthetic method comprises: step 1, conducting a diazotization reaction on pyridazol using a pipe reactor under the action of hydrochloric acid and isoamyl nitrite in a THF solvent to obtain diazonium salt; and step 2, conducting a coupling reaction on the diazonium salt and salicylic acid in a sodium hydroxide aqueous solution. In the synthetic method provided by the present invention, pyridazol is used as the raw material, and salazosulfapyridine is obtained through the diazotization reaction and the coupling reaction successively, . The diazotization reaction and the coupling reaction have a relatively high conversion rate and relatively few side reactions, thereby improving the product purity and ensuring the yield. In addition, pyridazol is easily available in source, so that the production cost is lowered, and the method has relatively huge industrial production value.

Description

technical field [0001] The invention relates to the technical field of sulfasalazine, in particular to a method for synthesizing sulfasalazine with sulfasalazine as a raw material. Background technique [0002] Sulfasalazine (SASP), also known as 5-[p-(2-pyridinesulfamoyl)benzene]azosalicylic acid. Molecular formula is C 18 h 14 N 4 o 5 S, molecular weight: 398.39. Its molecular structural formula is as follows: [0003] [0004] SASP is mainly used for the treatment of non-specific ulcerative colitis. This product has a special affinity for connective tissue and plays a therapeutic role by releasing sulfapyridine and 5-aminosalicylic acid in the intestinal wall. It is also used clinically for the treatment of rheumatic joints inflammation. Although this product is an old product, the market demand is still very large, especially its quality requirements are getting higher and higher. [0005] In the prior art, there are few disclosures on its purification method....

Claims

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Application Information

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IPC IPC(8): C07D213/76
CPCC07D213/76
Inventor 苏子钦徐伏彪江尔胜
Owner 苏州统华药品有限公司
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