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Synthesis method for valnemulin hydrochloride

A technology of vonimulin hydrochloride and a synthesis method, which is applied in the preparation of thioethers, organic chemistry and other directions to achieve the effects of strong antibacterial activity, clear antibacterial mechanism and low residues

Inactive Publication Date: 2013-11-06
LANZHOU INST OF ANIMAL SCI & VETERINARY PHARMA OF CAAS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

According to relevant domestic journals (Feng Dexin, Li Xinle, etc., 2010) and foreign patents or journal reports (Wang, X. Ling, Y. 2012; Zhang Y. Y., Xu K. P., 2010; US 7612103B2), generally the reaction time is longer and the conditions are relatively harsh

Method used

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  • Synthesis method for valnemulin hydrochloride
  • Synthesis method for valnemulin hydrochloride
  • Synthesis method for valnemulin hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Dissolve 75.7g (0.2mol) of pleuromutilin and 42g (0.22mol) of p-toluenesulfonyl chloride in a mixed solution of 200ml of methyl tert-butyl ether and 40mL of distilled water. mol / ml NaOH solution 50ml. Then it was heated to reflux while vigorously stirring. After 20 minutes, a large amount of white matter was formed, and it was stirred for another 20 minutes. The resulting white solid was filtered with a Buchner funnel, washed with methyl tert-butyl ether and distilled water, and dried naturally to obtain a white powder product with a yield of 97.8%.

Embodiment 2

[0045] Dissolve 37.9g ​​(0.1mol) of pleuromutilin and 22.9g (0.12mol) of p-toluenesulfonyl chloride in a mixed solution of 80ml of methyl tert-butyl ether and 20mL of distilled water, and slowly stir the mixture and drop it into 30ml of 0.01mol / ml NaOH solution. Then it was heated to reflux while vigorously stirring. After 30 minutes, a large amount of white matter was formed, and it was stirred for another 20 minutes. The resulting white solid was filtered with a Buchner funnel, rinsed with methyl tert-butyl ether and distilled water, and dried naturally to obtain a white powder product with a yield of 97.1%.

Embodiment 3

[0047] Dissolve 37.9g ​​(0.1mol) of pleuromutilin and 20.9g (0.11mol) of p-toluenesulfonyl chloride in a mixed solution of 100ml of methyl tert-butyl ether and 25mL of distilled water, and slowly stir the mixture and drop it into 30ml of 0.01mol / ml NaOH solution. Then it was heated to reflux while vigorously stirring. After 30 minutes, a large amount of white matter was formed, and it was stirred for another 20 minutes. The resulting white solid was filtered with a Buchner funnel, washed with methyl tert-butyl ether and distilled water, and dried naturally to obtain a white powder product with a yield of 96.8%.

[0048] mp 147~148 oC; IR (KBr): 3446, 2924, 2863, 1732, 1633, 1597, 1456, 1371, 1297, 1233, 1117, 1035, 832, 664, 560 cm-1; 1H NMR (400 MHz, CDCl3) δ 0.63 (d, 3H, J = 6.8 Hz), 0.87 (d, 3H, J = 6.8Hz), 1.11–1.15 (m, 1H), 1.22-1.26 (s, 5H), 1.33–1.36 (m , 1H), 1.41–1.44 (m, 1H), 1.46-1.50 (m, 5H), 1.63-1.65 (dd, 2H,J1=10Hz,J2=7.2 Hz), 2.01–2.08(m, 3H), 2.21 –2.29 (m,...

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Abstract

The invention discloses a synthesis method for valnemulin hydrochloride. The synthesis method comprises the steps: with pleuromutilin, dimethyl cysteamine and D-valine as main raw materials, carrying out amino protection, pleuromutilin activation, hydrocarbylation, acylation and deamination protection reactions, and ultimately preparing to obtain valnemulin hydrochloride. The synthesis method is suitable for industrialized production, and has the main advantages that: 1, during the reaction process and without need of column separation, valnemulin hydrochloride with higher content is obtained; 2, a used solvent has small toxicity, can also be recycled, does not pollute the environment, and is suitable for industrialized production; 3, a reaction condition is mild and is generally between 0-70 DEG C, and higher temperature and lower temperature reactions does not exist; and 4, the total yield is higher and reaches 50% or more.

Description

Technical field [0001] The present invention involves a synthesis method of Dinimelin hydrochloric acid, which is an organic synthetic field. Background technique [0002] Valnemulin Hydrochloride (Jie Song is as follows) The second -generation short -sides dedicated to animals was first developed by Sandoz in 1984. Its antibacterial spectrum is relatively wide.Positive bacteria, such as splin bacteria, gymiopulsee, and pylori, have good antibacterial activity. The in vitro-bacteriostatic effect is 10-100 times that of Thai Bangin, and the biological utilization is close to 100%.In 1999, Voni Poor Hydrochloride was approved by the European community to prevent or treat the pig dysentery caused by the infection caused by Brachyspira Hyodysenteriae infection and pig local pneumonia caused by pneumonia.It is the first premissions of animal drugs approved in Europe and is listed as a beast prescription drug.Listed in Poland and Hungary in 2000 for the treatment of pig diarrhea and e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/52C07C319/20
Inventor 尚若锋梁剑平郭文柱刘宇郝保成王学红郭志廷华兰英
Owner LANZHOU INST OF ANIMAL SCI & VETERINARY PHARMA OF CAAS
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