Euconafil oxide as well as preparation method and application thereof

A technique of Eucrena, quality control method, applied in the field of Eucrenafil oxide and its preparation, to achieve the effects of mild reaction conditions, easy availability of raw materials, and simple refining steps

Pending Publication Date: 2022-05-06
YANGTZE RIVER PHARM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, there are still continuous needs and uncertainties in the quality control methods of eucnafil and its salts and / or the improvement of its drug safety and stability, and the research results are very important for the application and development of the drug. significance

Method used

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  • Euconafil oxide as well as preparation method and application thereof
  • Euconafil oxide as well as preparation method and application thereof
  • Euconafil oxide as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0095]

[0096] To 100 mL of formic acid, add 10 g of free base of ucnafil hydrochloride (that is, the compound shown in formula II, also known as ucnafil), stir to dissolve, cool down to -5 ~ 5 ℃, slowly add 4.5 g of 30% concentration After adding the hydrogen peroxide solution, the temperature was slowly raised to 70-80° C., the reaction was incubated for 5 h, and controlled by TLC (developing solvent: volume ratio of ethyl acetate and ethanol=5:1) until the reaction was completed. Add 100mL of 1mol / L sodium bisulfite solution to the reaction solution, stir for 30min, add 40mL of purified water and 200mL of dichloromethane, stir for 30min, and extract by liquid separation. After the obtained organic phase is washed with 100mL of saturated sodium chloride solution, Dry with anhydrous sodium sulfate for 2h. Filtration, the filtrate was concentrated to dryness under reduced pressure at 30~40°C, then 40 g of ethanol was added, the temperature was raised to 70~80°C, the system...

Embodiment 2

[0098]

[0099] To 45mL of formic acid, add 5g of the compound of the structure shown in formula II, stir and dissolve, cool to -5~5°C, slowly add 3.0g hydrogen peroxide solution with a concentration of 30%, be warming up to 70~80°C after adding, and keep the reaction 4h, controlled by TLC (developing solvent: volume ratio of ethyl acetate and ethanol=5:1) to completion of the reaction. 50mL of 1mol / L sodium bisulfite solution was added to the reaction solution, stirred for 30min, added with 25mL of purified water and 100mL of dichloromethane, stirred for 30min, and subjected to liquid separation extraction. The obtained organic phase was washed with 50mL of saturated sodium chloride solution, and then Dry with anhydrous sodium sulfate for 2h. Filtration, the filtrate was concentrated to dryness under reduced pressure at 30-40 °C, 25 g of ethanol was added, the temperature was raised to 70-80 °C, the system was dissolved and then cooled to -5-5 °C, crystallized, filtered, a...

Embodiment 3

[0101]

[0102] In 45mL of acetic acid, add 5g of the compound of the structure shown in formula II, stir and dissolve, cool down to -5~5°C, slowly add 3.0g hydrogen peroxide solution with a concentration of 30%, be warming up to 70~80°C after adding, and keep the reaction 5h, controlled by TLC (developing solvent: volume ratio of ethyl acetate and ethanol=5:1) to completion of the reaction. 50mL of 1mol / L sodium bisulfite solution was added to the reaction solution, stirred for 30min, added with 25mL of purified water and 100mL of dichloromethane, stirred for 30min, and subjected to liquid separation extraction. The obtained organic phase was washed with 50mL of saturated sodium chloride solution, and then Dry with anhydrous sodium sulfate for 2h. Filtration, the filtrate was concentrated to dryness under reduced pressure at 30-40 °C, 25 g of ethanol was added, the temperature was raised to 70-80 °C, the system was dissolved and then cooled to -5-5 °C, crystallized, filter...

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Abstract

The invention discloses an uconafil oxide as shown in a formula I or pharmaceutically acceptable salt thereof, and a preparation method and application of the compound. The impurity is a degradation impurity of the uconafil hydrochloride, can be used as a reference substance for research of related substances, and is used for methodological verification and quality control of the uconafil hydrochloride so as to better control the product quality.

Description

[0001] This application claims to enjoy the priority rights of the prior invention patent application with the application number 202011205349.0 and the title of "Uconafil oxide and its preparation method and use" filed with the State Intellectual Property Office of China on November 2, 2020. The entirety of this application is incorporated herein by reference. technical field [0002] The present invention relates to the field of medicinal chemistry, in particular to ucnafil oxide and a preparation method and application thereof. Background technique [0003] Erectile Dysfunction (ED) refers to the persistent inability to achieve and / or) maintain a sufficient erection for a satisfying sexual life. According to statistics, there are currently many males with different degrees of ED in the world, and the number of patients will double by 2025. There are many treatment options for ED, among which selective phosphodiesterase 5 (PDE5) inhibitors are the most mature ED treatment...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61K31/519A61P15/10G01N30/02G01N30/06G01N30/34G01N30/36G01N30/74
CPCC07D487/04A61K31/519A61P15/10G01N30/02G01N30/06G01N30/34G01N30/36G01N30/74
Inventor 刘旭梁慧兴曹兵戴华山尹利献翟佳平
Owner YANGTZE RIVER PHARM GRP CO LTD
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