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Preparation method of animal antibiotic tulathromycin

A technology for teramycin and antibiotics, which is applied in the field of preparation of teramycin and the synthesis of medicines, can solve the problems of serious environmental pollution, difficult product purification and treatment, difficult reaction control, etc., and achieves reduction of production cost and simple reaction operation. easy effect

Active Publication Date: 2014-02-19
UNIV OF SCI & TECH BEIJING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0020] This method uses the highly toxic reagent sodium cyanide, which seriously pollutes the environment. The reducing agent uses lithium aluminum hydride, which can also reduce the ester group while reducing the cyano group, and the last step uses n-bromopropane, so the reaction is difficult to control in the secondary amine stage, product purification is very difficult

Method used

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  • Preparation method of animal antibiotic tulathromycin
  • Preparation method of animal antibiotic tulathromycin
  • Preparation method of animal antibiotic tulathromycin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] (1) Add oxycyclone C (0.65 g) and 15 ml methanol to a 50 ml one-necked bottle, then add triethylamine and nitromethane (0.22 ml). Heat to reflux, react for 48 h, and monitor the reaction by TLC plate. After the reaction was completed, the system was concentrated, and dichloromethane was added, and the organic layer was successively washed with NaHSO 3 Solution, water and saturated brine were washed, the organic phase was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain nitromethylene adduct D with a yield of 75%.

[0039] (2) Add nitromethylene adduct D (2 g) and 20 ml methanol to a 50 ml single-necked bottle, and reduce with sodium hydrosulfite (4 g). After the reaction is completed, concentrate the system and add dichloromethane to dissolve it. Dry over sodium sulfate and evaporate the solvent to obtain protected methyleneamine E with a yield of 81%.

[0040] (3) Add protected methyleneamine E (0.7 g) and 25 ml methanol to a 50 ...

Embodiment 2

[0044] (1) Add Oxycyclone C (1.3 g) and 25 ml methanol into a 50 ml one-necked bottle, then add triethylamine and nitromethane (0.45 ml), heat to reflux, react for 48 h, and monitor the reaction by TLC plate. After the reaction was completed, the system was concentrated, and dichloromethane was added, and the organic layer was successively washed with NaHSO 3 Solution, water and saturated brine were washed, the organic phase was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain nitromethylene adduct D with a yield of 78%.

[0045] (2) Add nitromethylene adduct D (4 g) and 30 ml methanol into a 50 ml single-necked bottle, and reduce it with Raney nickel hydrazine hydrate. After the reaction is completed, concentrate under reduced pressure, and then dichloromethane Extraction, drying over anhydrous sodium sulfate, evaporation of the solvent to obtain protected methyleneamine E, yield 84%.

[0046] (3) Add protected methyleneamine E (1.4 g) a...

Embodiment 3

[0050] (1) Add Oxycyclone C (3.25 g) and 50 ml methanol into a 100 ml single-necked bottle, then add triethylamine and nitromethane (1.2 ml), heat to reflux, react for 48 h, and monitor the reaction by TLC. After the reaction was completed, the system was concentrated, and dichloromethane was added, and the organic layer was successively washed with NaHSO 3 Solution, water and saturated brine were washed, the organic phase was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain nitromethylene adduct D with a yield of 84%.

[0051] (2) Add nitromethylene adduct D (10 g) and 100 ml methanol into a 250 ml single-necked bottle, and reduce it with hydrosulfite (20 g). After the reaction is completed, concentrate the system and add dichloromethane to dissolve it. Anhydrous sodium sulfate is dried, and the methyleneamine E that the solvent is evaporated to dryness is protected, yield 87%

[0052] (3) Add protected methyleneamine E (3.5 g) and 80 ml...

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Abstract

The invention belongs to the technical field of organic synthesis and pharmaceutical chemistry and especially relates to a preparation method of an animal antibiotic tulathromycin. According to the preparation method, azithromycin A and acetic anhydride which are used as raw materials are subjected to protection and oxidation to obtain oxide cyclic ketone; the intermediate is used for innovative addition of cyclic ketone and nitromethane; an addition product is reduced to obtain methyleneamine; direct condensation between methyleneamine and propionaldehyde is carried out; and reduction is conducted to obtain the high-purity target compound. Raw materials which are cheap and easily available are adopted. The preparation method has advantages of simple reaction, easily-controlled reaction process, high product purity, manageability, high yield, low cost and the like, and is suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to a method for synthesizing medicine, and relates to a method for preparing telamycin by using azithromycin A as a raw material. It belongs to the technical fields of organic synthesis and medicinal chemistry. Background technique [0002] Tyramycin, English tulathromycin, also known as tulathromycin and tolamycin, is a new type of animal-specific macrolide semi-synthetic antibiotic developed by Pfizer of the United States. It is a mixture of two isomers with a 13-membered azalide ring (10%) and a 15-membered azalide ring (90%), and the molecular formula is C 41 h 79 N 3 o 12 , molecular weight 806.09, chemical structure formula is: [0003] [0004] Tyramycin is a broad-spectrum antibacterial drug for animals. Because of its high antibacterial activity, broad antibacterial spectrum, and long half-life, it has been approved for use by many developed countries and has become the main drug for the treatment of animal respir...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/00C07H1/00
Inventor 杨运旭杨超
Owner UNIV OF SCI & TECH BEIJING
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