Synthesis method of cefpirome sulfate

A technology of cefpirome sulfate and synthesis method, applied in directions such as organic chemistry, can solve the problems of few reaction steps and high production cost, and achieve the effects of few reaction steps, convenient operation and reduced production cost

Inactive Publication Date: 2019-04-19
淄博鑫泉医药技术服务有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthetic approaches introduced above have been quite proficient in industrial applications, but these synthetic approaches have advantages, such as simple and easy operation, few reaction steps, and can obtain products with higher purity and better quality, but they also have their own limitations, but The production costs required in these synthetic routes are high, in order to further reduce production costs and maximize benefits, we will provide a new synthetic method

Method used

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  • Synthesis method of cefpirome sulfate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] (1) Synthesis of Compound A

[0037] 25g of GCLE and 17.9g of AE active ester were added to a mixed solvent of 400ml of dichloromethane and 80ml of ethanol, stirred and cooled to -5°C, and 7.7ml of triethylamine and 1.2ml of pyridine were added dropwise. At this temperature, stir until dissolved, continue to react for 2h, heat up to 18°C, add 300ml of purified water, stir for 15min, let stand for 10min, separate the liquid, collect the aqueous phase, add 180ml of purified water to the organic phase, stir for 15min, let stand for 10min, Separation, combining the two aqueous phases, adding 20% ​​dilute hydrochloric acid dropwise to adjust the pH to 3.0 for crystallization, cooling to 5°C, filtering, rinsing with ethanol, and vacuum drying to obtain 23.5 g of compound A with a yield of 82.95%.

[0038] (2) Synthesis of Compound B

[0039] Add 7.7 g of sodium iodide as an activator to 380 ml of acetone and stir until it dissolves clearly, add compound A, stir at room tempe...

Embodiment 2

[0043] (1) Synthesis of Compound A

[0044] 25g of GCLE and 17.9g of AE active ester were added to a mixed solvent of 400ml of dichloromethane and 80ml of ethanol, stirred and cooled to -5°C, and 7.7ml of triethylamine and 1.2ml of pyridine were added dropwise. At this temperature, stir until dissolved, continue the reaction for 2.5h, heat up to 18°C, add 300ml of purified water, stir for 15min, let stand for 10min, separate the liquid, collect the aqueous phase, add 180ml of purified water to the organic phase, stir for 15min, and let stand for 10min , separate the liquids, combine the two aqueous phases, add 15% dilute hydrochloric acid dropwise to adjust the pH to 3.0 for crystallization, cool to 5°C, filter, rinse with ethanol, and vacuum dry to obtain 22.5 g of compound A with a yield of 81.42%.

[0045] (2) Synthesis of Compound B

[0046] Add 7.7 g of sodium iodide as an activator to 380 ml of acetone and stir until it dissolves clearly, add compound A, stir at room te...

Embodiment 3

[0050](1) Synthesis of Compound A

[0051] 25g of GCLE and 17.9g of AE active ester were added to a mixed solvent of 400ml of dichloromethane and 80ml of ethanol, stirred and cooled to -3°C, 2.1g of sodium bicarbonate was added, 1.2ml of pyridine was added dropwise, and the temperature when the dropwise addition was completed did not exceed 0°C, Control the temperature, stir until dissolved, continue the reaction for 3h, heat up to 19°C, add 300ml of purified water, stir for 15min, stand for 10min, separate the liquid, collect the aqueous phase, add 180ml of purified water to the organic phase, stir for 15min, and let stand for 10min , the liquids were separated, the two aqueous phases were combined, 22% dilute hydrochloric acid was added dropwise to adjust the pH to 3.0 for crystallization, cooled to 5°C, filtered, rinsed with ethanol, and dried in vacuo to obtain 24.2 g of compound A with a yield of 83.23%.

[0052] (2) Synthesis of Compound B

[0053] Add 8.9 g of activato...

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Abstract

Belonging to the technical field of cefpirome drug synthesis, the invention in particular relates to a synthesis method of cefpirome sulfate. The method includes: taking GCLE and AE active ester as the raw materials for reaction under the action of alkali and a catalyst, performing extraction, using dilute hydrochloric acid to adjust pH and performing crystallization to obtain a compound A; addingan activating agent into an organic solvent, performing stirring till dissolving clarification, adding the compound A, adding 2, 3-cyclopentenopyridine dropwise to precipitate solid, thus obtaining acompound B; adding the compound B into a mixed solvent of water and alcohol, conducting heating stirring till dissolution, using sulfuric acid to adjust the pH value and performing crystallization toobtain cefpirome sulfate. The method provided by the invention adopts GCLE as the raw materials, avoids the use of expensive catalyst, and the used solvent and activating agent are cheap and easily available, thus greatly reducing the production cost. The synthesis method provided by the invention has the advantages of simple synthetic process route, few reaction steps, convenient operation and few side reaction, and the prepared cefpirome sulfate has high purity and yield.

Description

technical field [0001] The invention belongs to the technical field of cefpirome drug synthesis, and in particular relates to a method for synthesizing cefpirome sulfate. Background technique [0002] As a fourth-generation cephalosporin antibiotic, cefpirome has stronger antibacterial effect, broader antibacterial spectrum, and maintains effective blood drug concentration for a longer time, especially for neutropenic patients with infections, severe lower respiratory tract infections, Septicemia, bacteremia, concurrent infection of upper and lower urinary tract, skin and soft tissue infection, multi-drug resistant Enterobacteriaceae, Citrobacter, and ceftazidime hydrolase-producing Klebsiella and Escherichia coli have effects. [0003] Cefpirome Sulfate was launched in Mexico and Sweden in 1992 under the trade name Cefrom, and has now been listed in nearly 20 countries around the world. It has a superior ability to penetrate the outer membrane of bacteria, has an antibacte...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/04C07D501/46
CPCC07D501/04C07D501/46
Inventor 常明珠张立明张艳红
Owner 淄博鑫泉医药技术服务有限公司
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