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A kind of synthetic method of tediroxin intermediate

A technology of tediloxine and synthesis method, which is applied in chemical instruments and methods, organic chemistry, sugar derivatives, etc., can solve the problems of low product purity, cumbersome purification process, and high iodine activity, and achieves high product purity and high product quality. The effect of high yield and simple separation process

Active Publication Date: 2020-03-17
SHANDONG JIULONG HISINCE PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this method, the iodination reaction needs to be carried out to 2 hydroxyl groups in the reaction, and the activity of iodine is high, and the 4 hydroxyl groups on 20-hydroxyl-23-iodine-5-O-mycaminosyl-tylonolactone All have the opportunity to carry out iodination reaction, resulting in relatively low product purity, and the post-treatment purification process is cumbersome

Method used

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  • A kind of synthetic method of tediroxin intermediate
  • A kind of synthetic method of tediroxin intermediate
  • A kind of synthetic method of tediroxin intermediate

Examples

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Comparison scheme
Effect test

Embodiment 1

[0041] Example 1 Synthesis of 20-piperidinyl-23-iodo-5-O-mycaminosyl-tylonolide

[0042] In the 500L reactor, drop into 71.5kg20-piperidinyl-5-O-mycaminosyl-tylonolide (1) and stir in 160kg acetonitrile, add hydriodic acid (57%) of 44.1kg, reflux reaction After 4.5 hours (the reaction kettle is connected to the tail gas absorption tank), concentrate under reduced pressure until there is almost no solvent, add water, adjust the pH to 11 with sodium hydroxide solution, stir for 20 minutes, filter with suction, and dry to obtain the product 20-piperidinyl- 23-iodo-5-O-mycaminosyl-tylonolide (2) 63.0kg, yield 95.4%, purity 98.1%.

Embodiment 2

[0043] Example 2 Synthesis of 20-piperidinyl-23-iodo-5-O-mycaminosyl-tylonolide

[0044] In the 500L reactor, drop into 71.5kg20-piperidinyl-5-O-mycaminosyl-tylonolide (1) and stir in 160kg acetonitrile, add hydriodic acid (57%) of 44.1kg, reflux reaction After 4.5 hours (the tail gas absorption tank is connected to the reaction kettle), concentrate under reduced pressure until there is almost no solvent, add water, adjust the pH to 12 with sodium hydroxide solution, stir for 20 minutes, filter with suction, and dry to obtain the product 20-piperidinyl- 23-iodo-5-O-mycaminosyl-tylonolide (2) 63.2kg, yield 95.8%, purity 98.3%.

Embodiment 3

[0045] Example 3 Synthesis of 20-piperidinyl-23-iodo-5-O-mycaminosyl-tylonolide

[0046] In the 500L reactor, drop into 71.5kg20-piperidinyl-5-O-mycaminosyl-tylonolide (1) and stir in 160kg acetonitrile, add hydriodic acid (57%) of 39.5kg, reflux reaction After 4.5 hours (the tail gas absorption tank is connected to the reaction kettle), concentrate under reduced pressure until there is almost no solvent, add water, adjust the pH to 12 with sodium hydroxide solution, stir for 20 minutes, filter with suction, and dry to obtain the product 20-piperidinyl- 23-iodo-5-O-mycaminosyl-tylonolide (2) 62.9kg, yield 95.3%, purity 98.5%.

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Abstract

The invention belongs to the technical field of chemical synthesis, and in particular relates to a synthesis method of a tedirosin intermediate 20-piperidinyl-23-iodine-5-O-mycaminosyl-tylonolide. The method comprises the steps of: reflux reaction of 20-piperidinyl-5-O-mycaminosyl-tylonolide and hydroiodic acid to obtain 20-piperidinyl-23-iodine-5-O-carbamylamide Glycosyl-Tylonolactone. The method has the advantages of simple treatment process, small amount of waste liquid, low environmental protection treatment cost, high product yield and high purity of the obtained product.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a tedirosin intermediate and a tedirosin synthesis method. Background technique [0002] The new chemical formula of tedrol is C 41 h 71 N 3 o 8 , its chemical name is 20,23-dipiperidinyl-5-O-mycaminosyl-tylonolide, and its structural formula is: [0003] [0004] Tildipirosin is the latest animal-specific macrolide semi-synthetic antibiotic developed by Intervet International BV in the Netherlands. It is a derivative of tylosin. Sterile injection (trade name: ) was approved by the European Medicines Agency (EMA) for marketing in EU countries in 2011. It is used to prevent and treat respiratory infectious diseases in pigs and cattle caused by sensitive bacteria such as Haemophilus parasuis, Actinobacillus pleuropneumoniae, Pasteurella multocida and Mannheimia hemolyticus. After a single intramuscular injection or subcutaneous injection, Tedirosin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H1/00C07H17/08
CPCC07H1/00C07H17/00
Inventor 马居良殷习栋杨统鹏郑真真宋晶晶赵延东
Owner SHANDONG JIULONG HISINCE PHARMA CO LTD