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A kind of preparation method of sulfasalazine impurity d
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A technology for sulfasalazine and impurities, which is applied in the field of drug impurity synthesis, can solve problems such as easy residues and difficult removal, and achieve the effects of convenient purification, high reaction efficiency, and strong operability
Active Publication Date: 2022-03-08
TLC NANJING PHARMA RANDD CO LTD
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Problems solved by technology
Sulfasalazine impurity D, as one of its most important impurities, is easy to have residues in the production process, and it is difficult to remove, so the pure sulfasalazine impurity D is obtained, and sulfasalazine and sulfasalazine The properties, harm to the human body and metabolic mechanism of pyridine impurity D have important medical research value, and there is no report on the synthesis method of sulfasalazine impurity D
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Embodiment 1
[0041] Such as figure 1 Shown, a kind of preparation method of sulfasalazine impurity D, comprises the following steps:
[0042] (1) Dissolve 100.0 g of p-nitrobenzenesulfonyl chloride in 6 L of dioxane, add 110.5 g of sodium ethoxide (prepared from metal sodium and absolute ethanol) at 40° C. and react overnight. TLC spotting shows that the raw materials are completely reacted. Treatment: Add 1L of water and 500mL of ethyl acetate to extract to obtain intermediate II (92.4g, 88%) as a yellow solid;
[0043] (2) Dissolve 50.0g of intermediate II in 500mL of ethanol, add 15.0g of Rey-Ni hydrogenation balloon at room temperature and react overnight, TLC spot plate shows that the reaction of the raw materials is complete, filter the reacted mixture with suction, and spin the filtrate to obtain a yellow solid Intermediate III (42.0 g, 96%);
[0044] (3) Dissolve 20.0g of intermediate III in 500mL of dichloromethane, add 61.1g of mCPBA, and react at 25°C for 2h. TLC spotting shows ...
Embodiment 2
[0052] Such as figure 1 Shown, a kind of preparation method of sulfasalazine impurity D, comprises the following steps:
[0053] (1) Dissolve 100g of p-nitrobenzenesulfonyl chloride in 3L of THF, add 153.5g of sodium ethoxide (prepared from metal sodium and absolute ethanol), and react overnight at 60°C. TLC spotting shows that the raw materials have reacted completely, and add 1L of water , 500mL of ethyl acetate was extracted to obtain 100.8g of yellow solid intermediate II, with a yield of 96%;
[0054] (2) Dissolve 50.0g of intermediate II in 1L of ethanol, add 10.0g of palladium-calcium carbonate, and react overnight with a hydrogenation balloon at room temperature. TLC spotting shows that the reaction of the raw materials is complete. The reaction mixture is suction filtered, and the filtrate is spin-dried to obtain a yellow solid intermediate III (43.1 g, 99%);
[0055] (3) Dissolve 20.0g of intermediate III in 500mL of dichloromethane, add 70.5g of peracetic acid, an...
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Abstract
The invention discloses a preparation method of sulfasalazine impurity D, which belongs to the field of pharmaceutical impurity synthesis, and provides a method with reasonable process design, strong operability, easy purification of products, high purity, high yield, and industrial production. The preparation method of sulfasalazine impurity D. The present invention takes p-nitrobenzenesulfonyl chloride and 2-nitrophenol as starting materials, synthesizes sulfasalazine EP impurity D through 9 steps of reaction, screens out the optimal preparation steps and reaction conditions through a large number of experiments, and the whole process The design is reasonable and the operability is strong. The purity of the sulfasalazine impurity D prepared by the invention can reach more than 98%, and the yield can reach more than 80%. The sulfasalazine impurity D prepared by the present invention can provide a standard product for sulfasalazine research, can be used to explore the metabolic process of the drug in vivo, and has great application research value in clinical pharmacokinetic research.
Description
technical field [0001] The invention belongs to the field of drug impurity synthesis, in particular to a preparation method of sulfasalazine impurity D. Background technique [0002] Sulfasalazine {5-[p-(2-pyridinesulfamoyl)benzene] azosalicylic acid} is a sulfonamide antibacterial drug, and its structural formula is: [0003] [0004] Pfizer of the United States was listed in Switzerland in 1941, and has antibacterial, antirheumatic and immunosuppressive effects. Sulfasalazine is decomposed into sulfapyridine and 5-aminosalicylic acid by the bacteria in the intestinal tract, and sulfapyridine has a weak antibacterial effect, and it mainly acts as a carrier in the drug molecule, preventing 5-aminosalicylic acid from And the duodenum absorption, only under the alkaline condition of the intestine, the intestinal microorganisms break the diazo bond and release the active ingredient. The mechanism is currently considered to be mainly the complexation of 5-aminosalicylic acid...
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