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Original-quality ceftriaxone sodium and pharmaceutical preparation thereof

A technology of ceftriaxone sodium and ceftriaxone, which is applied in the field of pharmaceutical preparation, can solve the problems of affecting yield, increasing reaction steps, increasing production costs, etc., and achieves the effects of reducing reaction steps and reducing operation difficulty

Active Publication Date: 2016-03-23
广东金城金素制药有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This not only increases the reaction steps, but also requires the use of more expensive condensing agents, which not only affects the yield, but also increases the production cost

Method used

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  • Original-quality ceftriaxone sodium and pharmaceutical preparation thereof
  • Original-quality ceftriaxone sodium and pharmaceutical preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Embodiment 1: Preparation of 7-ACT

[0021] Add 100 mL of acetonitrile, 40 g (147 mmol) of 7-ACA, and 40.4 g (254 mmol) of TTA into a three-necked flask, stir and cool down to below 10°C, add 150 mL of boron trifluoride-acetonitrile solution [w / w=18%], and heat up to 30°C, react for 30 minutes. Add 300 mL of purified water within 15 minutes, raise the temperature to 10°C-20°C and react for 2 hours, add ammonia water to adjust the pH of the reaction solution to 1.6-2.0, and cool down to 10°C. After filtering, the filter cake was washed with acetonitrile-water and water, and dried to obtain 48g of 7-ACT with a yield of 85.71%.

Embodiment 2

[0022] Embodiment 2: the preparation of CTR

[0023] Add 100mL of acetonitrile, 100mL of dichloromethane, 10g (50mmol) of acetioxamic acid, 15.3g (150mmol) of triethylamine into a three-neck flask, stir and cool down to -5°C-0°C, and slowly dropwise add 5.2g (55mmol) of methyl chloroformate , Stir at -5°C-0°C for 1 h, rise to room temperature and stir for 4 h, add 18.6 g (50 mmol) of 7-ACT, and continue stirring for 6 h. After the reaction is complete, add 200mL of purified water, stir for 10min, let stand to separate layers, discard the organic phase, add the water phase to a three-necked flask, add 9g of sodium acetate solid, stir to dissolve, slowly add about 200mL of acetone dropwise at room temperature, and cool down to 0- At 5°C, continue to add 600 mL of acetone dropwise. After the dropwise addition, grow the crystal for 2 hours, filter, wash the filter cake with 100 mL of acetone, and dry to obtain 27.1 g of ceftriaxone sodium. Yield 82%, purity 99.87%.

Embodiment 3

[0024] Embodiment 3: the preparation of CTR

[0025] Add 100mL of acetonitrile, 100mL of dichloromethane, 10g (50mmol) of amothioxamic acid, 15.3g (150mmol) of triethylamine into a three-necked flask, stir and cool down to -5°C-0°C, and slowly dropwise add 5.45g (50mmol) of ethyl chloroformate , Stir at -5°C-0°C for 1 h, rise to room temperature and stir for 4 h, add 18.6 g (50 mmol) of 7-ACT, and continue stirring for 6 h. After the reaction is complete, add 200mL of purified water, stir for 10min, let stand to separate layers, discard the organic phase, add the water phase to a three-necked flask, add 9g of sodium acetate solid, stir to dissolve, slowly add about 200mL of acetone dropwise at room temperature, and cool down to 0- At 5°C, continue to add 600 mL of acetone dropwise. After the dropwise addition, grow the crystal for 2 hours, filter, wash the filter cake with 100 mL of acetone, and dry to obtain 27.5 g of ceftriaxone sodium. Yield 83.14%, purity 99.85%.

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Abstract

The invention discloses original-quality ceftriaxone sodium and a pharmaceutical preparation thereof. The key technology and industrialization of the third generation of cephalosporin antibiotics active ester intermediate wins the second prize of National Scientific and Technological Progress Award, and the third generation of cephalosporin antibiotics intermediate AE active ester is a key factor for affecting the internal quality of the ceftriaxone sodium. A preparation method comprises the steps that 1, boron trifluoride-acetonitrile serves as a catalyst, and on the condition that acetonitrile serves as solvent, a triazine ring is reacted with 7-ACA to generate 7-ACT; 2, triethylamine and aminothiazoly loximate are added into the solvent, a chloroformate activator is dropwise added slowly during cooling mixing, the 7-ACT is added for a one-pot reaction after stirring is conducted, and ceftriaxone is obtained; 3, a salt-forming agent is added, and the ceftriaxone sodium is obtained. According to the preparation method, use of a condensing agent with higher price is avoided, the process route is shortened, operation is easy, the reaction condition is mild, the product yield is high, the purity is good, and industrial production is easy.

Description

technical field [0001] The invention relates to medicine preparation technology, in particular to a kind of original developed quality ceftriaxone sodium and its medicine preparation. Background technique [0002] Ceftriaxone sodium, the English name is CeftriaxoneSodium, referred to as CTR, the chemical name is (6R,7R)-7-[[(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-8 -Oxo-3-[[(1,2,5,6-tetrahydro-2-methyl-5,6-dioxo-1,2,4-triazin-3-yl)thio]methanol Base]-5-thia-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid disodium salt triple hemihydrate. Its chemical structural formula is as follows: [0003] [0004] Ceftriaxone sodium is a broad-spectrum long-acting antibiotic launched by Swiss Roche Company in 1982. It has a small dosage, low toxicity and side effects, and a blood half-life of up to 8 hours. It has a large market share and is the third generation of broad-spectrum antibacterial activity. cephalosporins. Clinically, it is mainly used for respiratory tract infe...

Claims

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Application Information

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IPC IPC(8): C07D501/36C07D501/04C07D501/12C07D417/12A61K31/546A61P31/04
CPCA61K31/546C07D417/12C07D501/04C07D501/12C07D501/36
Inventor 傅苗青赵叶青孙滨许蕾朱旭伟马庆双周白水王雷
Owner 广东金城金素制药有限公司
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