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Novel method for preparing tulathromycin

A technology of telamycin and norazithromycin, which is applied to the preparation of sugar derivatives, chemical instruments and methods, and the production of bulk chemicals, and can solve problems such as complicated operation process and unfavorable industrial production

Active Publication Date: 2012-07-18
SHANDONG LUKANG SHELILE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, the operation process of these preparation methods is relatively complicated, especially the need to use high-pressure hydrogenation equipment and cryogenic conditions, which is not conducive to industrial production

Method used

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  • Novel method for preparing tulathromycin
  • Novel method for preparing tulathromycin
  • Novel method for preparing tulathromycin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-13-[[2,6-dideoxy-3-C-methyl-3-O-methyl-α-L -nucleo-hexapyranosyl]-oxy]2-ethyl-3,4,10-trihydroxy-3,5,8,10,12,14-hexamethyl-11-[[3,4, 6-trideoxy-3-(dimethylamino)-2-O-acetyl-β-D-xyl-hexapyranosyl]oxy]-1-oxa-6-azacyclopentadecane (15 -Yuan macrocycle) (intermediate one) preparation

[0058] Add 7.34 g (0.01 mol) of norazithromycin to a 250 ml round bottom flask, dissolve it with 40 ml of dichloromethane and place it in an ice bath, then add 1.4 ml of triethylamine (0.01 mol), and then add 1.5 ml of triethylamine after 20 minutes ml acetic anhydride (0.015 mol), react in the ice bath for 20 minutes, then remove the ice bath, react at room temperature for 10 hours, then add 1.0 ml acetic anhydride (0.01 mol), react for another 8 hours, stop the reaction, pour into the reaction system Add 50 ml of 1M sodium dihydrogen phosphate solution, stir at room temperature for 30 minutes, separate the organic phase, then extract the aqueous phase 3...

Embodiment 2

[0062] (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-13-[[2,6-dideoxy-3-C-methyl-3-O-methyl-4-oxo Substituent-α-L-nucleo-hexapyranosyl]-oxy]2-ethyl-3,4,10-trihydroxyacid-3,5,8,10,12,14-hexamethyl-11- [[3,4,6-trideoxy-3-(dimethylamino)-2-O-acetyl-β-D-xyl-hexapyranosyl]oxy]-1-oxo-6-aza Preparation of cyclopentadecane (15-membered macrocycle) (intermediate 2)

[0063] Add 2.05 g (25 mmol) of intermediate formula II to a 100 ml single-necked round bottom flask, dissolve it with 25 ml of dry dichloromethane at room temperature, add 532 ul dimethyl sulfoxide (75 mmol), stir well and place React at low temperature for 15 minutes, then add 1.5 ml trifluoroacetic anhydride (0.0106 mol) dropwise, continue to react for 1 hour, add 3 ml triethylamine (0.021 mol), stir at low temperature for 30 minutes, then naturally warm to room temperature, close to room temperature Add 30 ml of saturated NaCl solution, after 30 minutes, separate the organic phase, extract the aqueous phase with chloroform 5 t...

Embodiment 3

[0067] (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-13-[[2,6-dideoxy-3-C-methyl-3-O-methyl-4-C -[epoxymethyl]-α-L-nucleo-hexapyranosyl]-oxy]2-ethyl-3,4,10-trihydroxy-3,5,8,10,12,14-hexa Methyl-11-[[3,4,6-trideoxy-3-(dimethylamino)-2-O-acetyl-β-D-xyl-hexapyranosyl]oxy]-1-oxa - Preparation of 6-azacyclopentadecane (15-membered macrocycle) (intermediate 3)

[0068] Add 1.38 g (0.008 mol) of trimethylsulfur bromide, 25 ml of dry tetrahydrofuran and 8.8 ml of 1M potassium hexamethyldisilazide (0.008 mol) into a 100 ml single-necked round bottom flask, place at -15 After reacting for 1 hour at low temperature under the protection of argon, add 10ml tetrahydrofuran dissolved in 2.04 g (0.0025 mol) of intermediate 3 to the reaction system, react at low temperature for 30 minutes, transfer to room temperature, and use 20 ml saturated chlorinated The ammonium solution was extracted, stirred at room temperature for 30 minutes, and the organic phase was separated, the aqueous phase was extracte...

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Abstract

The invention discloses a novel method for preparing tulathromycin and relates to a semi-synthetic macrolide antibiotic. The method comprises the following steps: simultaneously protecting 2'-hydroxyl and 6a-amino of desmethyl azithromycin with acetyl, then carrying out oxidation and epoxidation on 4''-hydroxy, then removing the protecting groups under alkaline alcohol solution conditions, and carrying out nucleophilic addition on 4''-epoxy group with n-propylamine to obtain the target compound tulathromycin. Compared with the prior art, the method for preparing tulathromycin has the advantages of simple process, mild conditions, high yield and the like, and is beneficial to industrial production.

Description

technical field [0001] The invention relates to a semi-synthetic macrolide antibiotic, in particular to a new method for preparing telamycin. Background technique [0002] Macrolide antibiotics are a class of weakly basic antibiotics and their structural modifications produced by Streptomyces. Most of them are basic lipophilic compounds with high inhibitory activity against Gram-positive bacteria and mycoplasma. In 1952, Eli Lilly launched the first-generation macrolide antibiotic product erythromycin, and now it has launched the second-generation and even the third-generation macrolide antibiotic products. Among them, erythromycin A (erythromycin A) is a clinically representative first-generation macrolide antibiotic, which is isolated from S. erythreus and has a strong antibacterial effect on Gram-positive bacteria , Gram-negative bacteria such as meningococcus, Neisseria gonorrhoeae, influenza bacillus, pertussis bacilli, Brucella, etc. and Legionella (Legionella) are al...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H17/00C07H1/00
CPCY02P20/55
Inventor 郭强周妮妮董坤彭欣颜丙春桑艳丽
Owner SHANDONG LUKANG SHELILE PHARMA
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