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Synthetic method of isotope-labeled erythromycylamine

A technology of isotope labeling and synthesis method, which is applied in the field of drug synthesis and achieves the effects of reasonable process design, strong operability and short synthesis method route.

Active Publication Date: 2020-07-17
TLC NANJING PHARMA RANDD CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

What is reported in the literature at present is the synthetic method of non-labeled erythromycinamine, and there is no synthetic method of isotope-labeled erythromycinamine reported in the literature

Method used

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  • Synthetic method of isotope-labeled erythromycylamine
  • Synthetic method of isotope-labeled erythromycylamine
  • Synthetic method of isotope-labeled erythromycylamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Such as figure 1 Shown, a kind of synthetic method of isotope-labeled erythromycylamine comprises the following steps:

[0027] (1) Get 20g of erythromycin, add it to a 150mL round-bottomed flask, dissolve it with 50mL of methanol, then add 10g of hydroxylamine hydrochloride and 8g of potassium carbonate successively, and react for 48 hours at 20°C to obtain a white suspension; filter and spin the filtrate Dry, then add 100mL of water, adjust the pH to 10 with 25% ammonia water under ice bath conditions, a white solid precipitates out, filter to obtain 18g of intermediate II, which is a white solid, and the yield is 88.20%;

[0028] (2) Dissolve 18g of intermediate II in 90mL of methanol, slowly add 3g of sodium borohydride under ice bath conditions, and react for 8 hours at 20°C. The TLC board monitors that the raw materials have reacted completely. Add 300mL of water to the reaction solution, and use two Chloromethane extraction, the dichloromethane phase was separat...

Embodiment 2

[0034] Such as figure 1 Shown, a kind of synthetic method of isotope-labeled erythromycylamine comprises the following steps:

[0035] (1) Take 20g of erythromycin, add it to a 150mL round-bottomed flask, dissolve it with 50mL of methanol, then add 10g of hydroxylamine hydrochloride and 13g of triethylamine in sequence, and react at 20°C for 48 hours to obtain a white suspension; filter and filtrate Spin dry, then add 100mL of water, adjust the pH to 10 with 25% ammonia water under ice bath conditions, a white solid precipitates out, filter to obtain 12g of intermediate II, which is a white solid, and the yield is 55.80%;

[0036](2) Dissolve 12g of intermediate II in 120mL of methanol, slowly add 6g of lithium borohydride under ice bath conditions, react at 40°C for 8 hours, monitor the complete reaction of the raw materials on a TLC board, add 300mL of water to the reaction solution, and use two Chloromethane extraction, the dichloromethane phase was separated, concentrated...

Embodiment 3

[0042] Such as figure 1 Shown, a kind of synthetic method of isotope-labeled erythromycylamine comprises the following steps:

[0043] (1) Get 20g of erythromycin, add it to a 150mL round-bottomed flask, dissolve it with 50mL of ethanol, then add 10g of hydroxylamine hydrochloride, 8g of potassium carbonate, and react at 40°C for 12 hours to obtain a white suspension; filter and spin the filtrate Dry, then add 100mL of water, adjust the pH to 10 with 25% ammonia water under ice bath conditions, a white solid precipitates out, filter to obtain 14g of intermediate II, which is a white solid, and the yield is 68.60%;

[0044] (2) Dissolve 14g of intermediate II in 90mL of methanol, slowly add 3g of lithium borohydride under ice bath conditions, and react for 8 hours at 20°C. The TLC board monitors the complete reaction of the raw materials. Add 300mL of water to the reaction solution, and use two Chloromethane extraction, the dichloromethane phase was separated, concentrated, an...

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Abstract

The invention discloses a synthetic method of isotope-labeled erythromycylamine, belongs to the field of drug metabolism, and provides a synthetic method which is reasonable in process design, strongin operability and high in yield, can efficiently convert isotope-labeled raw materials into labeled target products, and can realize industrial production of isotope-labeled erythromycylamine. The method takes 13CD3 labeled methyl iodide as a starting raw material, the isotope-labeled erythromycylamine is synthesized by six steps of reactions, optimal preparation steps and reaction conditions arescreened out through a large number of experiments, the whole process is reasonable in design and high in operability, the labeled raw materials can be efficiently converted into labeled target products, the chemical purity of the labeled erythromycylamine prepared through the method can reach 98.5% or above, and the labeled isotope abundance is larger than 98.5%.

Description

technical field [0001] The invention belongs to the field of drug synthesis, in particular to a method for synthesizing isotope-labeled erythromycinamine. Background technique [0002] Dirithromycin is a Schiff base prodrug, which is decomposed into erythromycin in the body. Clinically, dirithromycin belongs to macrolide antibiotics and is a prodrug of erythromycin. Compared with lactone antibiotics, dirithromycin has the following characteristics: in addition to retaining the antibacterial effect on G+ bacteria, dirithromycin still has a strong effect on various G- bacteria, anaerobic bacteria and other pathogens, such as mycoplasma, chlamydia and spirochetes. Antibacterial effect; dirithromycin against Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pyogenes, Streptococcus agalactiae, Moraxella catarrhalis, Helicobacter pylori, Neisseria gonorrhoeae, Klebsiella pneumoniae, Haemophilus influenza Bacillus, Clostridium aerogenes, and Propionibacterium acnes ...

Claims

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Application Information

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IPC IPC(8): C07H17/08C07H1/00
CPCC07H17/08C07H1/00C07B2200/05
Inventor 张帅胡永铸刘春徐一鸣崔希林
Owner TLC NANJING PHARMA RANDD CO LTD
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