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Synthetic method of tildipirosin

A synthesis method and tediloxine technology, applied in the field of biomedicine, can solve the problems of difficult to control the impurity content of the final product, complicated purification process, numerous process steps, etc., and achieve high industrial application value, high reaction yield, raw material Safe and easy to get effect

Inactive Publication Date: 2016-03-30
宁夏泰瑞制药股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method has many process steps, resulting in a low total yield of about 67% to 71%.
Moreover, the polarity of the hydrolyzed product is similar to that of the halogenated compound, so it is not easy to separate, and the purification process is relatively complicated. The final product needs to be separated by chromatography, which further increases the cost, and it is difficult to control the impurity content in the final product.

Method used

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  • Synthetic method of tildipirosin
  • Synthetic method of tildipirosin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] In the new production line of 100kg class Tadiro, the 2m 3 Put 100kg of tylosin tartrate into the glass-lined main reaction kettle, add 500kg of purified water, stir and raise the temperature to 55°C until the tylosin is completely dissolved. The pH was adjusted to 1.0 by using 24% hydrobromic acid prepared in advance, and the reaction was incubated for 8 hours.

[0030] After the reaction is completed, to 2m 3 Add 250kg of dichloromethane into the glass-lined main reaction kettle, stir evenly, then use 20% sodium hydroxide solution to adjust the pH of the water phase to 9.2, continue stirring until uniform, let stand to separate the liquid, and separate the water phase.

[0031] Add 20kg of KBr into a 500L secondary reaction kettle, then add 10kg of NaClO, add 100kg of purified water, and stir until completely dissolved. with saturated NaHCO 3 Adjust the pH to 9.0.

[0032] to 2m 3 In the main reaction kettle, add 19.55kg (1.15eq) 2,2,6,6-tetramethylpiperidine nit...

Embodiment 2

[0035] In the new production line of 100kg class Tadiro, the 2m 3 Put 91.6kg of tylosin tartrate into the glass-lined main reaction kettle, add 367kg of purified water, stir and raise the temperature to 54°C until the tylosin is completely dissolved. The pH was adjusted to 0.8 by using 26% hydrobromic acid prepared in advance, and the reaction was incubated for 10 hours.

[0036] After the reaction is completed, to 2m 3 Add 113 kg of dichloromethane into the glass-lined main reaction kettle, stir evenly, then adjust the pH of the water phase to 9.4 with 22% sodium hydroxide solution, continue stirring until uniform, let stand to separate the liquid, and remove the water phase.

[0037] Add 20kg of KBr into a 500L secondary reaction kettle, then add 11kg of NaClO, add 120kg of purified water, and stir until completely dissolved. with saturated NaHCO 3 Adjust the pH to 8.8.

[0038] to 2m 3 In the main reaction kettle, add 18.52kg (1.17eq) 2,2,6,6-tetramethylpiperidine nitr...

Embodiment 3

[0041] In the new production line of 500kg class Tadiro, the distance is 10m 3 Put 458kg of tylosin tartrate into the glass-lined main reaction kettle, add 2060kg of purified water, stir and raise the temperature to 56°C until the tylosin is completely dissolved. The pH was adjusted to 0.6 by using 25% hydrobromic acid prepared in advance, and the reaction was incubated for 9 hours.

[0042] After the reaction is completed, to 10m 3 Add 515 kg of dichloromethane into the glass-lined main reaction kettle, stir evenly, then use 21% sodium hydroxide solution to adjust the pH of the water phase to 9.1, continue stirring until uniform, let stand to separate the liquid, and separate the water phase.

[0043]Add 100kg KBr into the 1500L secondary reaction kettle, then add 60kg of NaClO, add 550kg of purified water, and stir until completely dissolved. The pH was adjusted to 8.6 with saturated NaHCO3.

[0044] to 10m 3 In the main reactor, add 92.82kg (1.19eq) of 2,2,6,6-tetrameth...

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Abstract

The invention relates to a synthetic method of tildipirosin. The method comprises the following key synthetic steps: synthesizing 23-hydroxyl-20-carbonyl-5-O-carbon-enzyme glucosamine-tylactone in a one-pot method, synthesizing 20, 23-carbonyl-5-O-carbon-enzyme glucosamine-tylactone in a catalytic oxidation method and synthesizing the tildipirosin in a one-step ammoniation method. The tildipirosin is synthesized from tylosin only in three steps, so that the procedures are simple, the reaction yield is relatively high, the average total yield is 90 percent or more, and the purity of a final product is 98 percent or more; and moreover, all raw materials are safe and easy to get, byproducts are likely to recycle, and the industrialized application value is relatively high.

Description

technical field [0001] The invention belongs to the technical field of biomedicine, and in particular relates to a synthesis method of tedirosin. Background technique [0002] Tildipirosin is a new broad-spectrum antibacterial drug derived from tylosin, which has antibacterial activity against some Gram-positive and Gram-negative bacteria, especially against pathogenic bacteria that cause respiratory diseases in pigs and cattle. Sensitive, such as Actinobacillus pleuropneumoniae, Pasteurella multocida, Bordetella bronchiseptica, Haemophilus parasuis, Mannheimia hemolyticus, and Histophilia somnus. [0003] At present, the specific method for synthesizing tedirosin in China is as follows: first, hydrolyze the 23-glycosyl group, then halogenate the exposed 23-hydroxyl group after hydrolysis, and then react with piperidinyl group to obtain tedirosin. The method has many process steps, resulting in a low total yield of about 67-71%. Moreover, the hydrolyzate is similar in pola...

Claims

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Application Information

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IPC IPC(8): C07H17/08C07H1/00
CPCC07H17/08C07H1/00
Inventor 赵伯龙
Owner 宁夏泰瑞制药股份有限公司
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