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Preparation of florfenicol sodium succinate

A technology of florfenicol succinate and florfenicol, which is applied in chemical instruments and methods, preparation of organic compounds, pharmaceutical formulations and other directions, can solve problems such as difficult industrialized production, harsh chemical synthesis reaction conditions, high price, etc. problems, to achieve the effects of easy industrial production, improved bioavailability, and simple preparation methods

Inactive Publication Date: 2008-10-08
阮明华
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The methods for improving the water solubility of Florfenicol reported in the literature can be divided into two categories: one is that physical methods include adding cosolvent micronization, cyclodextrin inclusion, hydroxypropyl β-cyclodextrin inclusion, etc., such methods The solubilizing effect of florfenicol is generally unsatisfactory, the dissolution rate is slow, the dissolution rate is small, and it is difficult to meet the needs of preparations and concentrated preparations. The other is the chemical method, which is to make florfenicol into an inactive prodrug and metabolize it into fluorine after entering the animal body. The function of Benicol is characterized by its water solubility is much greater than that of physical methods
[0005] At present, the water solubility of florfenicol is mainly improved from the perspective of changing the dosage form in China, while foreign countries have started to modify and transform its structure and made florfenicol phosphate, which greatly improved its water solubility, but the product The chemical synthesis reaction conditions are harsh, the price is expensive, and it is difficult to realize industrial production

Method used

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  • Preparation of florfenicol sodium succinate
  • Preparation of florfenicol sodium succinate

Examples

Experimental program
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Effect test

Embodiment 1

[0017] 7.16 grams (0.02 moles) of Florfenicol, 6.07 grams (0.06 moles) of triethylamine, and 4 grams (0.04 moles) of succinic anhydride were added to a round-bottomed flask with a drying system filled with dichloromethane, Stir at 20°C, G254 thin-layer detection tracking (developing agent is chloroform:methanol:ethyl acetate:water=15:6:15:1 product Rf=0.32, florfenicol Rf=0.74), about 2 hours After the reaction was completed, the organic layer was washed with 10% hydrochloric acid, and then washed with water. The organic layer was dried over anhydrous sodium sulfate and concentrated to obtain 9 g of florfenicol succinate monoester with a yield of 98.3%.

[0018] 9 grams of the obtained florfenicol succinate monoester were dissolved in absolute ethanol, and reacted with sodium hydroxide solution at 10° C. to obtain 9.2 grams of florfenicol sodium succinate with a yield of 98%.

Embodiment 2

[0020] Add 7.16 grams (0.02 moles) of Florfenicol, 6.07 grams (0.06 moles) of triethylamine, and 4 grams (0.04 moles) of succinic anhydride into a round-bottomed flask with a drying system filled with chloroform, at 20°C Stir at low temperature for about 2 hours, wash the organic layer with 10% hydrochloric acid, wash with water, dry the organic layer with anhydrous sodium sulfate, and concentrate to obtain 8.5 g of florfenicol succinate monoester.

[0021] 8.5 grams of the obtained florfenicol succinate monoester was dissolved in absolute ethanol, and reacted with sodium hydroxide solution at 10° C. to obtain 8.7 grams of florfenicol succinate sodium with a yield of 98%.

Embodiment 3

[0023] 7.16 grams (0.02 moles) of Florfenicol, 6.07 grams (0.06 moles) of triethylamine, and 4 grams (0.04 moles) of succinic anhydride were added to a round-bottomed flask with a drying system filled with ethyl acetate, Stir at 20°C for about 2 hours, wash the organic layer with 10% hydrochloric acid, wash with water, dry the organic layer with anhydrous sodium sulfate, and concentrate to obtain 8.8 g of florfenicol succinate monoester.

[0024] 8.8 g of the obtained florfenicol succinate monoester was dissolved in absolute ethanol, and reacted with sodium hydroxide solution at 10° C. to obtain 9.0 g of florfenicol succinate sodium with a yield of 98%.

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Abstract

Disclosed is a method to prepare florfenicol sodium succinate. Florfenicol reacts with succinic anhydride in organic solvent with triethylamine as activator under 10-15 DEG C to produce florfenicol ester succinate which then reacts with sodium hydroxide in organic solvent under 10-15 DEG C, producing florfenicol sodium succinate which is soluble in water. The mol ratio of the materials of florfenicol: triethylamine:succinic anhydride is 1:2-4:1.5-3. Florfenicol sodium succinate preparation can be made into injection, aqueous solution and lyophilized powder and can be used for disease prevention and treatment on animals.

Description

technical field [0001] The invention discloses a preparation method of florfenicol sodium succinate (chemical name: florfenicol sodium succinate), which belongs to the technical field of organic chemical synthesis. Background technique [0002] Florfenicol (chemical name: florfenicol) is a new generation of chloramphenicol-like broad-spectrum antibiotics for animals. It has the characteristics of broad antibacterial spectrum, good absorption, wide distribution in the body, and high safety, especially without potential regeneration. Obstructive anemia, carcinogenic and mutagenic effects, and has a significant effect on animal diseases caused by sensitive bacteria. It is the first choice drug for the treatment of various infections caused by typhoid bacillus, paratyphoid bacillus and salmonella. The drug has been used in more than 20 countries Since chloramphenicol has a serious adverse reaction of causing aplastic anemia, it has been banned from being used in food animals. Th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/32C07C315/04A61K31/165A61P31/04
CPCY02A40/70
Inventor 阮明华
Owner 阮明华
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