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Preparation method for tulathromycin intermediate

A technology of tyramectin and intermediates, applied in the field of preparation of medicinal chemicals, can solve the problems of increasing difficulty in industrial production and the like

Inactive Publication Date: 2014-01-08
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
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AI Technical Summary

Problems solved by technology

[0004] The process routes reported above all use Swern oxidation reaction and cryogenic temperature control measures, and the reaction temperature is controlled at about -30°C~-80°C, which obviously increases the difficulty of industrial production

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0024] (1) In a clean and dry reaction bottle, put 9.0 g of norazithromycin compound Ⅰ whose hydroxyl group is protected by acetyl group and 50 ml of dichloromethane, cool down to -2°C in an ice-salt bath, and start stirring. Add 5ml of dimethyl sulfoxide and stir to dissolve. Then 3 ml of acetic anhydride was added, and the reaction was incubated for 3 hours. Neutralize with alkali and then extract with distilled water to separate the organic phase. The organic phase was dried over anhydrous sodium sulfate, filtered, and the filter cake was washed with dichloromethane. The solvent was distilled off under reduced pressure to obtain compound II with a yield of 90.9%.

[0025] (2) Add 30ml of 20% sodium hydroxide solution into the reaction bottle, then add 0.4g of trimethylsulfur iodide, and react at room temperature for 1 hour. Dissolve 2.05 g of compound II and 0.15 g of tetrabutylammonium bromide in 20 ml of dichloromethane. Added to the above system, heat preservation re...

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Abstract

The invention relates to a preparation method for a tulathromycin intermediate. The preparation method comprises the following steps: oxidizing 4'-hydroxyl of demethylazithromycin of which the hydroxyl is protected by acetyl under a mild condition to obtain ketone by using a dimethyl sulfoxide and acetic anhydride system, and continuing to epoxidize the obtained ketone to obtain an epoxide by using a phase transfer catalyst, wherein the intermediate epoxide of tulathromycin can be introduced into propylamine through an open loop, and is subjected to deprotection to obtain the tulathromycin. According to the reaction method, a phase transfer catalyst system is adopted for the first time in an exoxidizing process, reaction conditions are mild, and the method is high in yield and more suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of pharmaceutical chemicals, in particular, a preparation method of a telamectin intermediate. Background technique [0002] Tulathromycin (Tulathromycin), also known as soil (pictured) laramycin, is a macrolide semi-synthetic antibiotic for animals launched by Pfizer Animal Health in 2002. It was launched in the European Union and the United States in 2004. Tyramectin has excellent antibacterial activity and a super-long half-life superior to other antibiotics. It can maintain an effective therapeutic concentration in animals for 5-7 days with only one-time low-dose administration. It is used for the prevention and treatment of respiratory infectious diseases caused by sensitive bacteria in cattle and pigs and bovine infectious keratoconjunctivitis caused by Moraxella bovis. A single dose can provide a full course of treatment. Pigs generally take intramuscular injections , cattle to take subcutaneous inj...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/01C07H1/00
Inventor 吴汝林吴广启王凡业
Owner QINGDAO UNIV OF SCI & TECH
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