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Method for preparing cefathiamidide

A technology for cefathiamidine and cephalosporins is applied in the field of preparation of chemical raw material cefathiamidine, and can solve problems such as being difficult to realize, complicated and the like

Inactive Publication Date: 2005-07-20
托新权 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

USP3,646,025 and "Chinese Journal of Medicinal Chemistry", 2001, 10, No. 11, P293-294, introduced the synthesis method of this raw material, but they are all complicated and not easy to realize

Method used

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  • Method for preparing cefathiamidide
  • Method for preparing cefathiamidide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Embodiment 1, cefathiamic acid

[0019] 2.72g 7-ACA, 2.52g NaHCO 3 , 20ml H 2 O and 10ml of acetone were added into a three-necked flask, and stirred at room temperature (32° C.) until dissolved. Then the mixed solution was cooled to about -10°C, and 2.3 g of bromoacetyl bromide (dissolved in 10 ml of acetone) was slowly added dropwise. It took about 1.5 hrs, preferably no solids appeared. After the dropwise addition was completed, the reaction was continued at this temperature (25 D =+120°.

Embodiment 2

[0020] Embodiment 2, cefathiamidine finished product

[0021] Diisopropylthiourea was recrystallized.

[0022] Add 3.93g of cefathiamic acid and 50ml of dichloromethane into a 100ml three-necked flask, slowly add triethylamine to make it just clear (about 1.3ml), add 1.6g of diisopropylthiourea, stir at room temperature for 0.5h, the solution It becomes viscous, slowly add 50ml of acetone dropwise, crystallization begins to precipitate, continue to stir for 0.5h, filter, and wash with acetone. Vacuum dry. Obtain 3.41g of sulfur rice crude product. The yield is 75%, and the melting point is 148-150°C. Optical rotation value: [α] 25 D =139°. The product can be recrystallized from ethanol.

[0023] Elemental Analysis (C 19 h 28 N 4 O 6 S 2 ): C, 46.66; H, 6.41; N, 11.59.

[0024] IR (cm -1 ): 3427.54, 3225.12, 2979.67, 2938.91, 1773.98, 1737.52. m / z: 473, 413, 354, 275, 242, 201.

[0025] 1 HNMR (D 2 O): 5.60-5.59(1H), 5.11-5.10(1H), 4.86-4.83(1H), 4.69-4.66(1H)...

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Abstract

The preparation process of cefathiamidine includes the following two synthesis steps: 1) preparing cefathiamidine acid through the reaction between 7-ACA and bromoacetyl bromide, acidifying, solvent extraction, concentration and drying; and 2) preparing cefathiamidine product through adding alkali reagent to dissolve cefathiamidine acid, reaction with diisopropyl thiourea, and adding semi-soluble solvent to separate out cefathiamidine product. The said preparation process has less steps, and is simple and feasible.

Description

technical field [0001] The invention relates to the field of chemical drug synthesis, in particular to a preparation method of the chemical raw material drug cefathiamidine. Background technique [0002] Cefathiamidine (Cefathiamidine) is the first generation cephalosporin, which was first created and used clinically in my country. [0003] [0004] Commonly known as: pioneer mycin 18, cephalosporin 18. The antibacterial spectrum is similar to that of cephalothin, and it has a stronger effect on Staphylococcus aureus, Streptococcus viridans, and Pneumococcus, and has unique antibacterial activity against Enterococcus, and is mainly used for respiratory tract infections caused by Staphylococcus aureus, Pneumococcus, and Streptococcus, Biliary tract infection, urinary tract infection, gynecological infection, sepsis, pneumonia, meningitis and other infections. In my country, only Guangzhou Baiyunshan Chemical Pharmaceutical Factory produces it. USP3,646,025 and "Chinese ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/28
Inventor 江数范
Owner 托新权
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