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Water-soluble aureomycin succinic acid monoester salt and preparation method thereof

A technology of succinic acid monoester and chlortetracycline, applied in the field of water-soluble chlortetracycline succinic acid monoester salt and preparation thereof, can solve the problems of body irritation or pain, poor solubility, bad smell or taste, etc. The effect of promoting animal growth, good application prospects, and enhancing immunity

Active Publication Date: 2017-02-01
PUCHENG CHIA TAI BIOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Easy to decompose in water, poor chemical stability, poor solubility, bad smell or taste, irritating or painful to the body when used, etc.
Its preparation type and clinical application are subject to certain restrictions, and it also affects the due effect of aureomycin drugs

Method used

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  • Water-soluble aureomycin succinic acid monoester salt and preparation method thereof
  • Water-soluble aureomycin succinic acid monoester salt and preparation method thereof
  • Water-soluble aureomycin succinic acid monoester salt and preparation method thereof

Examples

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Effect test

Embodiment 1

[0028] Embodiment 1, the preparation of aureomycin succinic acid monoester sodium salt

[0029] Dissolve chlortetracycline hydrochloride (1.0mol) in 40% ethanol aqueous solution, add sodium carbonate (1.2mol) solid and stir, and stir the solution at 80°C to form a homogeneous phase; add succinic anhydride (5.0mol) and bicyclic Hexylcarbodiimide (1.2mol) was stirred under reflux for 3 hours, acidified to pH=6 with hydrochloric acid, and cooled to obtain aureomycin succinic acid monoester as a solid.

[0030] Dissolve the obtained aureomycin succinate monoester (1mol) in ethanol, reflux, add sodium hydroxide (1.0mol) in batches, stir, and cool to generate the target product aureomycin succinate monoester sodium salt . The product is light yellow powder with a yield of 77.8%. As determined by HPLC, the purity of the product was 98.6%; as determined by FAB-MS (fast atom bombardment mass spectrometry), the molecular weight of the product was 600.9, which was consistent with the t...

Embodiment 2

[0031] Embodiment 2, the preparation of aureomycin succinic acid monoester sodium salt

[0032] Dissolve chlortetracycline hydrochloride (1.0mol) in 90% acetone aqueous solution, add sodium carbonate (1.5mol) solid stirring, stir the solution at 60 ℃ and become homogeneous; Add succinic anhydride (1.2mol) and 4- Dimethylaminopyridine (1.8 mol), stirred at reflux for 0.5 hour, acidified with hydrochloric acid to pH=6, cooled to obtain aureomycin succinic acid monoester solid.

[0033] Dissolve the obtained aureomycin succinate monoester (1mol) in isopropanol, reflux, add sodium hydroxide (2.0mol) in batches, stir, and cool to generate the target product aureomycin succinate monoester sodium salt. The product is light yellow powder with a yield of 81.3%. As determined by HPLC, the purity of the product was 98.58%; as determined by FAB-MS, the molecular weight of the product was 600.1, which was consistent with the theoretically calculated molecular weight of the target product...

Embodiment 3

[0034] Embodiment 3, the preparation of aureomycin succinate monoester potassium salt

[0035] Dissolve chlortetracycline hydrochloride (1.0mol) in 70% aqueous ethylene glycol solution, add sodium carbonate (1.0mol) solid and stir, and stir the solution at 30°C to become homogeneous; add succinic anhydride (3.0mol) and Triethylamine (4.5mol) was stirred under reflux for 5 hours, acidified with hydrochloric acid to pH=6, and cooled to obtain aureomycin succinic acid monoester as a solid.

[0036] The obtained aureomycin succinic acid monoester (1mol) was dissolved in N,N-dimethylformamide, refluxed, and potassium hydroxide (1.5mol) was added in batches, stirred, and cooled to generate the target product gold Potassium monomycin succinate. The product is light yellow powder with a yield of 85.9%. As determined by HPLC, the purity of the product was 99.1%; as determined by FAB-MS, the molecular weight of the product was 617.2, which was consistent with the theoretically calcula...

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Abstract

The invention belongs to the technical field of chemical synthesis, and more specifically relates to a water soluble chlorotetracycline succinic acid monoester salt, and a preparation method thereof. The preparation method is used for modifying chlorotetracycline. The chlorotetracycline succinic acid monoester salt possesses a structure represented by formula I, wherein M is used for representing Na, K, meglumine, arginine, or lysine. According to the preparation method, grafting modification of chlorotetracycline with succinic anhydride is carried out so as to obtain the chlorotetracycline succinic acid monoester salt with water solubility better than that of chlorotetracycline, and broad-spectrum antibacterial property of the water soluble chlorotetracycline succinic acid monoester salt is the same as that of chlorotetracycline in animal bodies.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to water-soluble chlortetracycline succinic acid monoester salt and a preparation method thereof. Background technique [0002] Chlortetracycline (CTC), a tetracycline antibiotic, is similar to tetracycline in chemical structure and only replaces H with Cl at the C-7 position, so chlortetracycline is also called 7-chlorotetracycline, and its structural formula is as follows: [0003] [0004] Chlortetracycline hydrochloride is golden yellow or yellow crystal, odorless, bitter taste, slightly soluble in water and ethanol solution, almost insoluble in acetone, ether, or chloroform, but soluble in alkaline hydroxide and in the carbonate solution. The specific rotation of aureomycin hydrochloride is between -235 and -250, and the pH value is between 2.3-3.3. Chlortetracycline has a broad antibacterial spectrum, and can inhibit Gram-positive bacteria, negative...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C237/26C07C231/12C07C279/14C07C277/08C07C229/26C07C227/18C07C215/10C07C213/00A61P31/04A23K20/195
Inventor 王建华马德寿冯献张雪峥
Owner PUCHENG CHIA TAI BIOCHEM
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