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Preparation method of cefathiamidine

A cefathiamidine, a single technology, applied in the field of preparation of cefathiamidine, can solve the problems of large solvent usage, cumbersome product purification process, reduction of solvent usage and usage types, etc., achieve simple recovery, avoid recrystallization and purification Steps, the effect of reducing the amount of precipitation

Inactive Publication Date: 2011-05-25
广东省石油化工研究院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The purpose of the present invention is to overcome the defects of large amount of solvent used and cumbersome product purification process in the existing technology for preparing cefathiamidine, and provide a preparation method of cefathiamidine, which does not need to add crystallization solvent for crystallization, greatly reducing The amount and type of solvent used can be determined, and high-purity cefathiamidine products can be obtained

Method used

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  • Preparation method of cefathiamidine
  • Preparation method of cefathiamidine

Examples

Experimental program
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Effect test

Embodiment 1

[0044] In a 500ml reaction bottle, add 10g of 7-bromoacetyl ACA and 5g of N,N-diisopropylthiourea into 150ml of dichloromethane, slowly add triethylamine: 25% ammonia water (volume ratio: 1:0.02) and mix Solution until the system is completely dissolved, control the temperature at 30°C, add 1.0g of activated carbon and stir for 30 minutes, filter through a 0.45 micron filter element to a sterile room, add triethylamine:ammonia water (volume ratio 1:0.1) mixed solution to adjust the pH to 5.5 , lower the temperature to 15°C, and continue to crystallize for 2 hours after the white solid starts to precipitate, filter, wash twice with acetone, 100ml each time, and finally vacuum-dry at 25°C for 3 hours. Obtain product 9.6g, yield 75%.

[0045] The obtained product has a purity of 98.6% and an optical rotation of 140°.

Embodiment 2

[0047] In a 500ml reaction bottle, add 10g of 7-bromoacetyl ACA and 5g of N,N-diisopropylthiourea into 150ml of dichloromethane, slowly add triethylamine: 25% ammonia water (volume ratio: 1:0.02) and mix Solution until the system is completely dissolved, control the temperature at 25°C, add 1.0g of activated carbon and stir for 30 minutes, filter through a 0.45 micron filter element to a sterile room, add acetic acid to adjust the pH to 4.0, lower the temperature to 20°C, and wait until white solids start to precipitate, Continue to crystallize for 3 hours, filter, wash with acetone twice, 100 ml each time, and finally vacuum-dry at 30° C. for 3 hours. Obtain product 9.7g, yield 76%.

[0048] The obtained product has a purity of 98.4% and an optical rotation of 140°.

Embodiment 3

[0050] In a 500ml reaction bottle, add 10g of 7-bromoacetyl ACA and 5g of N,N-diisopropylthiourea into 150ml of dichloromethane, slowly add triethylamine: 25% ammonia water (volume ratio: 1:0.01) and mix Solution until the system is completely dissolved, control the temperature at 30°C, add 1.0g of activated carbon and stir for 30 minutes, filter through a 0.45 micron filter element to a sterile room, add triethylamine: 25% ammonia water (volume ratio: 1:0.01) mixed solution to adjust the pH to 5.5, lower the temperature to 15°C, and continue to crystallize for 3 hours after white solids start to precipitate, filter, wash with acetone twice, 100ml each time, and finally vacuum-dry at 30°C for 3 hours. Obtain product 9.7g, yield 76%.

[0051] The obtained product has a purity of 98.6% and an optical rotation of 140°.

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Abstract

The invention discloses a preparation method of cefathiamidine. The method comprises the following steps: adding 7-bromoacetyl ACA and N,N-diisopropyl thiourea into a single solvent, performing reaction in the presence of a base catalyst which is complexed by organic base and inorganic base, performing crystallization by regulating the pH value of solution and the crystallization temperature under the situation of not adding a devitrification solvent after completing the reaction and getting a cefathiamidine product. With the adoption of the method, the product can be obtained with higher yield, and the purity of the obtained product can achieve the requirements of pharmacopoeia without recrystallization. The method is used for producing the cefathiamidine product, the process is simpler,the production cost is lower, the precipitation amount of impurities is reduced, and the purity of the obtained product is higher.

Description

technical field [0001] The invention relates to the field of chemical pharmacy, in particular to a preparation method of cefathiamidine. technical background [0002] Cefathiamidine, commonly known as cephalosporin 18 and cephalosporin 18, belongs to the first generation of cephalosporin antibiotics. Because the total effective rate against Gram-positive cocci (including drug-resistant bacteria) is 93.61%, it has a wide range of applications, including respiratory tract infections, urinary tract infections, skin and soft tissue infections, ear, nose and throat infections, sepsis, and biliary tract infections. , burns and surgical infections, gynecological infections, endocarditis and purulent meningitis and other infections have definite curative effect. [0003] The chemical name of cefathiamidine is (6R,7R)-3-[(acetoxy)methyl]-7-[a-(N,N-diisopropylthiamidino)acetamido]-8-oxo Dai-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid betaine, the molecular structure is sho...

Claims

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Application Information

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IPC IPC(8): C07D501/28C07D501/04
Inventor 翁行尚曾理文铭孝
Owner 广东省石油化工研究院