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Method for preparing cefquinome sulfate

A technology for cefquinoxime sulfate and cefquinoxime, which is applied in the field of chemical synthesis, can solve the problems of high synthesis cost, difficult handling, large amount of raw materials, etc., and achieves the effects of simple operation, reduced production cost and high yield

Inactive Publication Date: 2013-09-04
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] The purpose of this invention is to provide a kind of method for preparing cefquinome sulfate, to overcome the large amount of raw material that exists in the prior art, difficult to handle, the defective that synthetic cost is high

Method used

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  • Method for preparing cefquinome sulfate
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Examples

Experimental program
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Embodiment 1

[0031] (1) Preparation of Intermediate A

[0032] Add 13.6g of 7-aminocephalosporanic acid and 12.8g of triethylamine into 50mL of acetone, stir and react at 45°C for 3 hours, cool to room temperature, filter, wash with 100mL of deionized water three times, and dry in vacuo. Add 13.6 g of solids obtained by vacuum drying to 50 mL of acetone, add 21.0 g of 2-methoxyimino-2-(2-amino-4-thiazolyl)-(z)-thiocarbazone, add 4.1 g Triethylamine was stirred and reacted at 45°C for 2 hours. After the reaction was completed, 30 mL of deionized water was added, and the pH was adjusted to 1-2 with 2 mol / L sulfuric acid solution. Solid intermediate A was precipitated, filtered, washed, and vacuum-dried.

[0033] (2) Preparation of intermediate B (cefaquine hydroiodide)

[0034] Add the solid obtained in the above reaction step (1) to 50 mL of acetonitrile, add 12.5 g of potassium iodide and 1 mL of 95% phosphoric acid, react under reflux for 2 hours, filter, wash, and dry in vacuum to obtai...

Embodiment 2

[0038] (1) Preparation of Intermediate A

[0039] Add 13.6g of 7-aminocephalosporanic acid and 35.7g of ammonia water (35%) into 50mL of acetone, stir and react at 45°C for 3 hours, cool to room temperature, filter, wash with 100mL of deionized water three times, and dry in vacuo. Add 13.6g of light yellow solid obtained by vacuum drying into 50mL of acetone, add 21.0g of 2-methoxyimino-2-(2-amino-4-thiazolyl)-(z)-thiazolylthioate, Add 4.1 g of ammonia water, stir and react at 45°C for 2 hours, add 30 mL of deionized water after the reaction is complete, adjust the pH to 1-2 with 6 mol / L sulfuric acid solution, precipitate solid A, filter, wash, and vacuum dry.

[0040](2) Preparation of intermediate B (cefaquine hydroiodide)

[0041] Add the solid obtained in the above step (1) into 50 mL of acetonitrile, add 12.5 g of potassium iodide and 1 mL of 95% phosphoric acid, react under reflux for 2 hours, filter, wash, and vacuum dry. Add the obtained light yellow solid into 50mL...

Embodiment 3

[0045] (1) Preparation of Intermediate A

[0046] Add 13.6g of 7-aminocephalosporanic acid and 10.6g of sodium carbonate into 50mL of dichloromethane, stir and react at 50°C for 3 hours, cool to room temperature, filter, wash with 100mL of deionized water three times, and dry in vacuo. Add 13.7g of light yellow solid obtained by vacuum drying into 50mL of acetone, add 21.0g of 2-methoxyimino-2-(2-amino-4-thiazolyl)-(z)-dicarbazolylthioacetate, Add 12.8 g of triethylamine, stir and react at 45°C for 2 hours, add 30 mL of deionized water after the reaction, adjust the pH to 1-2 with 6 mol / L sulfuric acid solution, precipitate solid A, filter, wash, and vacuum dry.

[0047] (2) Preparation of intermediate B (cefaquine hydroiodide)

[0048] Add the solid obtained in the above step (1) into 50 mL of acetonitrile, add 11.8 g of sodium iodide and 1 mL of 95% phosphoric acid, react under reflux for 3 hours, filter, wash, and vacuum dry. Add the obtained light yellow solid into 50mL ...

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Abstract

The invention discloses a method for preparing cefquinome sulfate. The method comprises the steps as follows: 7-aminocephalosporanic acid is taken as a raw material; a C-3 bite ester group is hydrolyzed under the action of alkali and reacts with 2-(2-Amino-4-thiazolyl)-(z)-methoxyiminoacetic, thiobenzothiazole ester, so that an intermediate A is obtained; an iodo substance 3-iodine methyl cefotaxime is obtained through the intermediate and potassium iodide under the action of phosphoric acid; the 3-iodine methyl cefotaxime reacts with 5, 6, 7, 8-tetrahydroquinoline, so that an intermediate B of cefquinome hydriodate is obtained; and finally, the intermediate B of cefquinome hydriodate reacts with sulfuric acid under the action of an alkaline anion exchange resin, so that the cefquinome sulfate is obtained. According to the method for preparing the cefquinome sulfate, the 7-aminocephalosporanic acid which is cheap and easy to obtain is taken as the raw material, so that the use of iodotrimethylsilane which is expensive and prone to decompose when contacted with light and water is avoided, and the production cost is reduced; and the reaction condition is mild, the operation is simple, the yield is high, and the cefquinome sulfate is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for preparing animal-specific antibiotic raw materials, in particular to a method for preparing cefquinome sulfate, which belongs to the technical field of chemical synthesis. Background technique [0002] Cefquinome sulfate is the 4th generation animal-specific cephalosporin antibiotic developed by Hearst Company in the 1980s. It has been approved by the EU Veterinary Medicines Committee (CVMP) for respiratory tract bacterial infections in pigs and cattle and acute cattle infections. Mastitis and hoof disease, bovine septicemia, pig respiratory disease, sow metritis-mastitis-agalactia syndrome, lower respiratory tract and other serious infectious diseases. It has strong antibacterial activity, excellent pharmacokinetic characteristics, less toxic and side effects, and low residue. Compared with the second and third generation cephalosporins, it has the advantages of strong antibacterial activity, high bioavailability,...

Claims

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Application Information

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IPC IPC(8): C07D501/46C07D501/04
Inventor 赵地顺刘美端郑连义刘宝树葛京京汪学良李俊盼崔云胡晶晶
Owner HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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