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Synthesis of tulathromycin

A technology of telamycin and its compound, which is applied in the field of synthesis of telamycin, achieves good industrialization prospects and shortens the reaction time

Pending Publication Date: 2021-12-31
江苏君若药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The reaction conditions only use 10 times the equivalent of n-propylamine, but the reaction temperature is increased to 70 ° C, and the reaction time is also as long as 30 hours

Method used

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  • Synthesis of tulathromycin
  • Synthesis of tulathromycin
  • Synthesis of tulathromycin

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Embodiment 1

[0021] Embodiment one: the preparation of telamycin

[0022] Add (2R, 3S, 4R, 5R, 8R, 10R, 11R, 12S, 13S, 14R)-2-ethyl-3,4,10-trihydroxyl-13-[[3S,4S, 6R,8R]-8-methoxy-4,8-dimethyl-1,5-dioxaspiro[2,5]-oct-6-yl]oxy)3,5,8,10, 12,14-Hexamethyl-11-[[3,4,6-trideoxy-3-(dimethylamino)-β-D-hexylopyranosyl]oxy]-1-oxa- 6-Azacyclopentadecane-15-one monohydrate (compound formula I) (110g, 143.8mmol) and isopropanol (500mL) were stirred and dissolved at room temperature. Then n-propylamine (12.75g, 215.7mmol, 1.5eq) and ytterbium trifluoromethanesulfonate (8.9g, 14.4mmol, 0.1eq) were sequentially added to the reaction system. After the addition was complete, the system was heated to 50° C. and stirred for 3 hours. After the reaction is complete, the system is concentrated under high vacuum and reduced pressure to remove the organic solvent, add DMF (450mL) to the residue, heat to 80°C to dissolve, filter while hot, stir the filtrate slowly to about 5°C, stir and crystallize for 2 hours, ...

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Abstract

The invention relates to synthesis of tulathromycin, in particular to a reaction of (2R, 3S, 4R, 5R, 8R, 10R, 11R, 12S, 13S, 14R)-2-ethyl-3, 4, 10-trihydroxy-13-[[3S, 4S, 6R, 8R]-8-methoxy-4, 8-dimethyl-1, 5-dioxaspiro [2, 5] oct-6-yl] oxy) 3, 5, 8, 10, 12, 14-hexamethyl-11-[[3, 4, 6-trideoxy-3-(dimethylamino)-beta-D-xylopyranosyl] oxy]-1-oxa-6-azacyclopentadecane-15-one monohydrate with n-propylamine in the presence of a solvent and ytterbium trifluoromethanesulfonate, so as to realize the synthesis of tulathromycin.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to the synthesis of telamycin. Background technique [0002] Tulathromycin (Tulathromycin), also known as tulathromycin, tolamycin, trade name "Draxxin" (Chinese name is "Rui Kexin" or "Rui Kexin"). The drug is a new type of erythromycin synthetic veterinary drug researched and developed by Pfizer Animal Health in the late 1990s. It is a semi-synthetic macrolide antibiotic for animals and is mainly used to treat and prevent animal diseases. Respiratory diseases caused by Actinobacillus pleuropneumoniae, Mycoplasma, Pasteurella, Haemophilus para, Bordetella bronchiseptica, etc. A large number of studies have found that Tyramycin can selectively penetrate Gram-negative bacterial pathogens and is used for the treatment of respiratory infectious diseases caused by sensitive bacteria in cattle and pigs and bovine infectious keratitis caused by Moraxella bovis. prevention. The drug wa...

Claims

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Application Information

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IPC IPC(8): C07H17/00C07H1/00
CPCC07H17/00C07H1/00
Inventor 朱灿杨晓瑜裔明月刘洁姜军
Owner 江苏君若药业有限公司
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