Medicinal cefsulodin sodium compound and preparation method thereof
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A technology of cefsulodin sodium and its compounds, applied in the field of medicine, can solve problems such as insufficient safety, high cost, and low yield, and achieve the effects of high safety, low equipment requirements, and high yield
Active Publication Date: 2019-01-08
ZHEJIANG JIANFENG PHARM CO LTD +1
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Problems solved by technology
[0008] In order to solve the technical defects of high cost, insufficient safety and low yield in the existing preparation method
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Embodiment 1
[0043] like figure 2 As shown, add 8.0kg 7-ACA, 86.7kg dichloromethane, 14.5kg hexamethyldisilamine (HMDS) and 29ml concentrated sulfuric acid in a 200-liter reaction tank as a starter, and reflux the reaction tank after 4 hours. Cool down the temperature, maintain at -5 ~ 0 ℃, add 9.38kg trimethylsilyl iodide (TMS-I), stir and react for 3 hours, add 3.74kg isonicotinamide, slowly raise the temperature, reflux for 2 hours, and then react Cool the solution to 0°C, add 9.42kg of methanol, stir for 0.5 hours, add 35.2L of 6N hydrochloric acid, heat up to 20°C, stir for 0.5 hours, then extract the organic phase with 10kg of water, combine the water phases, transfer to a 150L reaction tank, and cool down to 0~5℃, add 6L 6.6% hydrogen peroxide aqueous solution, stir for 10 minutes after addition, filter, wash the filtered residue with 5kg water, combine the filtrate, add 3kg activated carbon and stir for decolorization for 1 hour, filter, wash with 5kg water The filter layer was c...
Embodiment 2
[0046] In above-mentioned embodiment 1, adopt 1.2-dichloromethane, dichloroethane, acetonitrile, N-N dimethylformamide, N-N dimethylacetamide, dimethyl sulfoxide, ethyl acetate, methyl acetate and acetic acid One or more of the butyl esters can replace dichloromethane as the organic solvent, and the target product 7-IACA can be prepared with the same technical characteristics, and the purity is 98.87%.
Embodiment 3
[0048] In the above-mentioned embodiment 1, one or more of trimethylchlorosilane, trimethyl iodosilane, N, O-bistrimethylsilylacetamide and bistrimethylsilylurea are used to replace hexamethyldimethoxysilane Silamine (HMDS) is used as a silicon protection reagent, and the target product 7-IACA can be prepared by adopting other identical technical features, with a purity of 98.87%.
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Abstract
The invention relates to the technical field of medicine, in particular to a medicinal cefsulodin sodium compound and a preparation method thereof. The preparation method of the medicinal cefsulodin sodium compound includes steps: 1) preparation of 3-(4-pyridinecarboxamide-1-methylene)-7-amino-cephalosporanic acid; 2) preparation of D-sulfophenylacetyl chloride; 3) preparation of D-sulfocephalosporanic acid; 4) preparation of cefsulodin sodium. The technical defects of high cost, low safety and low yield of existing preparation methods are overcome; by adoption of a silicon reagent method for preparation of the cefsulodin sodium compound, racemate controllability, high safety, high yield and high quality are realized, starting materials are easy to acquire, reaction conditions of each step are mild, equipment requirements are low, a single solvent is adopted and convenient to recycle, the requirement on environment friendliness can be met, and the method is suitable for large-scale industrial production.
Description
technical field [0001] The invention relates to the technical field of medicine, in particular to a cefsulodin sodium compound and a preparation method thereof. Background technique [0002] Cefsulodin sodium CAS NO.52152-93-9, Chinese alias (6R,7R)-3-[(4-carbamoylpyridin-1-ium-1-yl)methyl]-8-oxo-7 -[[(2R)-2-Phenyl-2-sulfoacetyl]amino]-5-thio-1-azabicyclo[4.2.0]oct-2-ene-2-sodium carboxylate, English name Cefsulodin sodium , formula C 22 h 19 N 4 NaO 8 S 2 , with a molecular weight of 554.53, was launched in Japan in February 1981 under the trade name of takesulin. [0003] Cefsulodin sodium was launched in Japan in 1981. Long-term clinical application has shown that this product has a good curative effect. The total effective rate of adult infection is 69%, and the effective rate of child infection is 72%. And it has good safety. The overall adverse reaction rate is about 5%, mainly manifested as nausea, vomiting and other gastrointestinal reactions, which recover sp...
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