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Florfeniol sulfonic acid ester, salt thereof and method for preparing same

A technology of sulfonic acid ester and florfenic acid, which is applied in the field of florfenicol sulfonic acid ester compounds and their preparation, can solve the problems of poor water solubility and strong irritation, and achieves reduced irritation, less irritation and excellent The effect of solubility

Inactive Publication Date: 2011-02-16
JIANGSU HANSYN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] Aiming at the shortcomings of poor water solubility and strong irritation of florfenicol compounds existing in the prior art, the invention provides a kind of florfenicol sulfonate and its salt and their preparation method, the fluorfenicol prepared by the invention Fenicol sulfonate and its salts have good water solubility, low irritation, and high conversion rate of hydrolysis to florfenicol in vivo

Method used

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  • Florfeniol sulfonic acid ester, salt thereof and method for preparing same
  • Florfeniol sulfonic acid ester, salt thereof and method for preparing same
  • Florfeniol sulfonic acid ester, salt thereof and method for preparing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Synthesis of Florfenicol Sulfonate Sodium Salt

[0051]

[0052] 1 in the above reaction formula is [1R, 2S-1-(4-methylsulfonylphenyl)-2-(2,2-dichloroacetylamino)-3-fluoropropyl]sulfonate

[0053] (1) Under nitrogen, add 50ml of pyridine to the three-necked flask, cool with ice-salt water, when the temperature drops to 0°C, add 24g (0.21mol) of chlorosulfonic acid dropwise, control the temperature not to exceed 10°C, and add it for about 1 hour use up. The temperature was naturally raised to 15° C., and 71 g (0.2 mol) of Florfenicol was added in batches. React at 15-20°C for 8 hours. After the end, 300ml of water was added to separate the oily compound 1.

[0054] (2) Add 4.5g of sodium metal to 300ml of absolute ethanol, cool to 0°C, and add dropwise to the oily substance under stirring. During this process, a small amount of solid precipitates out. After adding, place it for 2 to 5 hours , a large amount of white solid was precipitated, suction filtered, washed...

Embodiment 2

[0059] Synthesis of Ammonium Salt of Florfenicol Sulfonate

[0060] (1) Under nitrogen, add 30ml of triethylamine to the three-necked flask, cool with ice-salt water, when the temperature drops to 0°C, add 24g (0.21mol) of chlorosulfonic acid dropwise, and control the temperature not to exceed 10°C, about 1 Hours added. The temperature was naturally raised to 15° C., and 71 g (0.2 mol) of Florfenicol was added in batches. React at 15-20°C for 8 hours. After the end, 300ml of water was added to separate the oily compound 1.

[0061] (2) Pass 3.5g of ammonia gas into 300ml of absolute ethanol, cool to 0 ℃, and add dropwise to the oily substance under stirring. During this process, a small amount of solid precipitates out. Hours, a large amount of white solid precipitated, filtered with suction, washed with a small amount of ice ethanol, and dried to obtain florfenicol ammonium salt as a white solid.

[0062] The synthesis of florfenicol sulfonate protonated amine, amino diac...

Embodiment 3

[0064] Synthesis of Florfenicol Sulfonate Meglumine Salt

[0065] (1) Under nitrogen, add potassium carbonate 30g / toluene 80ml to the three-necked flask, cool with ice brine, when the temperature drops to 0°C, add 24g (0.21mol) of chlorosulfonic acid dropwise, and control the temperature not to exceed 10°C, Add about 1 hour. The temperature was naturally raised to 15° C., and 71 g (0.2 mol) of Florfenicol was added in batches. React at 15-20°C for 8 hours. After the end, 300ml of water was added to separate the oily compound 1.

[0066] (2) Add 40g of meglumine to 300ml of ethanol with a mass concentration of 80%, cool to 0°C, and add dropwise to the oily substance under stirring. During this process, a small amount of solid is precipitated. After 5 hours, a large amount of white solid precipitated, which was filtered by suction, washed with a small amount of ice ethanol, and dried to obtain Florfenicol meglumine salt as a white solid.

[0067] The synthesis of florfenicol...

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Abstract

The invention discloses a florfenicol sulphonic acid ester compound and a method thereof which comprises the following steps: an alkalescent reagent is used as a solvent singly or together with an inert reagent, chlorosulfonic acid is added under anaerobic conditions when the temperature ranges from 0 to 10 DEG C, then florfenicol is added in batches after chlorosulfonic acid is added, a materiellayer is separated after the reaction is performed for 2 to 12 hours, and then florfenicol sulphonic acid ester which is found in the form of acids is obtained; obtained florfenicol sulphonic acid ester which is found in the form of acids is mixed with the alcoholic solution of alkali containing acceptable monovalent cation in pharmacy, the reaction lasts for 2 to 5 hours, and florfenicol sulphonic acid ester salt taking the form of monovalent salt is prepared through filtering, washing and drying. Therefore, the salt form of florfenicol prodrug can be separated, and separated florfenicol prodrug containing acceptable monovalent cation is generated. The product which is obtained by adopting the method has good water-solubility, less stimulation, and high percent conversion for internal hydrolyzation into florfenicol.

Description

technical field [0001] The invention relates to a compound for preparing prodrugs of florfenicol, a salt thereof and a preparation method thereof, in particular to a florfenicol sulfonate compound and a preparation method thereof. Background technique [0002] Florfenicol, also known as florfenicol, is a structural analog of thiamphenicol, and thiamphenicol is a derivative of chloramphenicol. The relevant content of the background technology of the present invention mainly refers to U.S.4,235,892 and U.S. 5,352,832. [0003] [0004] Florfenicol Thiamphenicol Chloramphenicol [0005] Florfenicol is a new broad-spectrum chloramphenicol antibiotic for veterinary medicine. Its chemical name is D(+)-threo-1-p-methylfengylphenyl-2-dichloroacetamido-3-fluorophenyl alcohol. It has the characteristics of broad antibacterial spectrum, good absorption, wide distribution in the body, safety and high efficiency, and low incidence of drug resistance. Florfenicol has a strong killi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C317/32C07C315/00A61P31/04
Inventor 张军忍江善祥余祖功张汉兴
Owner JIANGSU HANSYN PHARMA
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