Synthetic method of Tildipirosin intermediate

A technology of tediloxine and synthesis method, which is applied in chemical instruments and methods, preparation of sugar derivatives, sugar derivatives, etc., can solve the problems of low product purity, high iodine activity, and complicated purification process, and achieve product purity. High, simple separation process, high product yield

Active Publication Date: 2018-11-16
SHANDONG JIULONG HISINCE PHARMA CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Synthetic method of Tildipirosin intermediate
  • Synthetic method of Tildipirosin intermediate

Examples

Experimental program
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Effect test

Embodiment 1

[0043] Example 1 Synthesis of 20-piperidinyl-23-iodo-5-O-mycaminosyl-tylonolide

[0044] In a 500L reactor, put 71.5kg of 20-piperidinyl-5-O-mycaminosyl-tylonolide (1) and 160kg of acetonitrile into stirring, add 44.1kg of hydroiodic acid (57%), and 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

[0045] Example 2 Synthesis of 20-piperidinyl-23-iodo-5-O-mycaminosyl-tylonolide

[0046] In a 500L reactor, put 71.5kg of 20-piperidinyl-5-O-mycaminosyl-tylonolide (1) and 160kg of acetonitrile into stirring, add 44.1kg of hydroiodic acid (57%), and reflux reaction After 4.5 hours (the tail gas absorption tank is connected to the reaction kettle), concentrate under reduced pressure to 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

[0047] Example 3 Synthesis of 20-piperidinyl-23-iodo-5-O-mycaminosyl-tylonolide

[0048] In a 500L reactor, put 71.5kg of 20-piperidinyl-5-O-mycaminosyl-tylonolide (1) and 160kg of acetonitrile and stir, add 39.5kg of hydroiodic acid (57%), and reflux the reaction After 4.5 hours (the tail gas absorption tank is connected to the reaction kettle), concentrate under reduced pressure to 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 particularly relates to a method for synthesizing a Tildipirosin intermediate 20-piperidinyl-23-iodine-5-O-mycaminose-tylactone.The method comprises the following steps of: 20-piperidinyl-5-O-mycaminose-tylactone and hydroiodic acid are subjected to a reflux reaction to obtain 20-piperidinyl-23-iodine-5-O-mycaminose-tylactone. The method has the advantages of simple treating process, small amount of waste liquid, low cost of treatment for environmental protection and high product yield; and the product obtained has high purity.

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. The sterile injection (trade name: Zuprevo®) with Tedirosin as the main active ingredient was reviewed by the European Medicines Agency (EMA) in 2011 and approved for marketing in EU countries. 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...

Claims

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Application Information

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Patent Type & Authority Applications(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
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