Method for preparing cephapirin benzathine

A technology for benzathine cefapirin and cefapirin acid, which is applied in the field of chemical drug synthesis and achieves the effects of easy operation, simplified steps and simple process

Active Publication Date: 2010-07-21
GUANGZHOU BAIYUNSHAN PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There is no record of benzathine cefapirin in the domestic pharmacopoeia, but it is recorded in the United States Pharmacopoeia

Method used

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  • Method for preparing cephapirin benzathine
  • Method for preparing cephapirin benzathine
  • Method for preparing cephapirin benzathine

Examples

Experimental program
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Embodiment 1

[0023] The preparation of embodiment 1 benzathine cefapirin

[0024] Add 1003 milliliters of acetone, 783 milliliters of methanol and 391 milliliters of water into the reaction vessel, add 50 grams of bromoacetyl 7-ACA, add 23 milliliters of triethylamine dropwise at 2-5 ° C, after dissolving, add 20 grams of 4-mercaptopyridine, React at 5-10°C for 5 hours. After completion, add 150 milliliters of water, 5 grams of sodium thiosulfate, and 20 grams of sodium bicarbonate. After the solid dissolves, add 5 grams of activated carbon, decolorize for 30 minutes, filter the charcoal, and wash the charcoal layer with 20 milliliters of water. Add 35 grams of DBED to the filtrate, react at 37 to 40°C for 6 hours, filter, wash the product with 3×300 milliliters of water, and dry in vacuo to obtain white solid benzathine cefepirin. The molar yield is 94~97%, adopts HPLC method to record and contain cefapirin acid 80% (USP29 standard is 71.5~82.0%), adopts titration method to measure and c...

Embodiment 2

[0026] Embodiment 2: the preparation of benzathine cefapirin

[0027] Add 1003 milliliters of acetone, 783 milliliters of methanol and 391 milliliters of water into the reaction vessel, add 50 grams of bromoacetyl 7-ACA, add 23 milliliters of triethylamine dropwise at 2 to 5 ° C, after dissolving, add 14 grams of 4-mercaptopyridine, React at 5-10°C for 5 hours. After completion, add 150 milliliters of water, 5 grams of sodium thiosulfate, and 20 grams of sodium bicarbonate. After the solid dissolves, add 5 grams of activated carbon, decolorize for 30 minutes, filter the charcoal, and wash the charcoal layer with 20 milliliters of water. Add 35 grams of DBED to the filtrate, react at 37 to 40°C for 6 hours, filter, wash the product with 3×300 milliliters of water, and dry in vacuo to obtain a yellowish solid benzathine cefepirin. The molar yield was 60%.

Embodiment 3

[0028] Embodiment 3: the preparation of benzathine cefapirin

[0029] Add 1003 milliliters of acetone, 783 milliliters of methanol and 391 milliliters of water into the reaction vessel, add 50 grams of bromoacetyl 7-ACA, add 23 milliliters of triethylamine dropwise at 2-5 ° C, after dissolving, add 20 grams of 4-mercaptopyridine, React at 5-10°C for 2 hours. After completion, add 150 milliliters of water, 5 grams of sodium thiosulfate, and 20 grams of sodium bicarbonate. After the solid dissolves, add 5 grams of activated carbon, decolorize for 30 minutes, filter the charcoal, and wash the charcoal layer with 20 milliliters of water. Add 35 grams of DBED to the filtrate, react at 37~40° C. for 6 hours, filter, wash the product with 3×300 milliliters of water, and vacuum-dry to obtain white solid benzathine cefepirin, and the molar yield is 89%.

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Abstract

The invention discloses a new method for preparing cephapirin benzathine by a one-pot method, relating to the field of chemical drug synthesis. The method comprises the following steps of: taking acetyl bromide 7-ACA as raw materials; in a solvent, in the presence of organic alkali, reacting the acetyl bromide 7-ACA with 4-pyridinethiols to obtain solid cefapirin acid; and then adding the organic alkali in the reaction liquid, dissolving the cefapirin acid as salt, and simultaneously and unnecessarily adding a reductant which is sodium thiosulfate, sodium hydrogensulfite or vitamin C; and then adding a reagent A in the reaction liquid, reacting the cefapirin acid salt with the reagent A at 0-50 DEG C for 0.1-20 hours to obtain the cephapirin benzathine, wherein the reagent A is dibezylethylenediamine diacetate acetate or dibezylethylenediamine diacetate. The method solves the problems that a product is easily decomposed, color is easily deepened in the process of preparing cefapirin sodium salt, and the like. The invention is simplified in steps, easy to operate and suitable for industrialized production, and the quality of the product accord with the quality standard of USP29.

Description

technical field [0001] The invention relates to the field of chemical drug synthesis, and more specifically relates to a new method for preparing benzathine cefepirin. Background technique [0002] Cephapirin Benzathine (Cephapirin Benzathine), its structural formula is as follows: [0003] [0004] Benzathine cefapirin is an amine salt complex of cefapirin, which belongs to the first generation of cephalosporin antibiotics. Benzathine cefapirin is effective against many Gram-positive and some Gram-negative bacteria and is highly effective against pneumococci and enterococci. It is mainly used for the treatment of urinary system infection, respiratory system infection and soft tissue infection caused by sensitive bacteria, such as the treatment of pyelitis, cystitis, osteomyelitis, sepsis, meningitis, endocarditis, etc. In addition to the efficacy of cefapirin, benzathine cefapirin has the advantage of long-acting effect, and is currently mainly used to treat mastitis i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/28
Inventor 傅海燕田美如
Owner GUANGZHOU BAIYUNSHAN PHARM CO LTD
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