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Apixaban impurity and synthesis method thereof

A technology of apixaban and synthetic method, which is applied in the field of drug synthesis, can solve problems such as human hazards and different physiological activities, and achieve the effect of perfecting quality standards

Inactive Publication Date: 2021-07-16
WEIFANG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Because organic impurities may have different physiological activities, they may cause harm to the human body

Method used

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  • Apixaban impurity and synthesis method thereof
  • Apixaban impurity and synthesis method thereof
  • Apixaban impurity and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] 50g of 6-(4-aminophenyl)-1-(4-methoxyphenyl)-(4-methoxyphenyl)-7-carbonyl-1H-pyrazolo[3,4-c ]-4,5,6,7-tetrahydropyridine-3-carboxylic acid methyl ester (commercially available product, CAS: 1466571-07-2) was added to the reaction flask, 500mL of DMF was added, 100g of formamide was added, and slowly added 8g of sodium methoxide, and then heated up to 45°C to keep the temperature for reaction, and monitored by TLC until the reaction of the raw materials was complete. Cool down to room temperature and add 1L of water. Extracted 3 times with ethyl acetate (500 mL each time), combined the organic phases and dried them with anhydrous magnesium sulfate, and evaporated the solvent under reduced pressure. A viscous oil was obtained.

[0049] Dissolve 30 g of the obtained viscous oil in methanol, add 50 g of silica gel (300-400 mesh) and mix well, then fully evaporate to dryness and apply the sample, and use silica gel chromatography (silica gel 300-400 mesh) for column chroma...

Embodiment 2

[0060] 50g of 6-(4-aminophenyl)-1-(4-methoxyphenyl)-(4-methoxyphenyl)-7-carbonyl-1H-pyrazolo[3,4-c ]-4,5,6,7-tetrahydropyridine-3-carboxylic acid ethyl ester (commercially available product, CAS: 503615-07-4) was added to the reaction flask, 500mL of DMF was added, 150g of formamide was added, and slowly added 26g of sodium hydroxide, and the temperature was raised to 80° C. for heat preservation reaction, and TLC was monitored until the reaction of the raw materials was complete. Cool down to room temperature and add 1L of water. Extracted 3 times with dichloromethane (500 mL each time), combined the organic phases and dried them with anhydrous magnesium sulfate, and evaporated the solvent under reduced pressure. Obtained 20 g of a viscous oil.

[0061] After dissolving the obtained viscous oil in methanol, add 50 g of silica gel (300-400 mesh) and mix well, then fully evaporate to dryness and apply the sample, and use silica gel chromatography (silica gel 300-400 mesh) for...

Embodiment 3

[0065] 50g of 6-(4-aminophenyl)-1-(4-methoxyphenyl)-(4-methoxyphenyl)-7-carbonyl-1H-pyrazolo[3,4-c ]-4,5,6,7-tetrahydropyridine-3-amide (commercially available product, CAS: 1423803-24-0) into the reaction flask, add 500mL of dichloromethane, add 200g of formamide, slowly add 25g Sodium methoxide, then heated up to 50°C and kept for reaction, monitored by TLC until the reaction of raw materials was complete. Cool down to room temperature and add 1L of water. Extracted 3 times with dichloromethane (500 mL each time), combined the organic phases and dried them with anhydrous magnesium sulfate, and evaporated the solvent under reduced pressure. Obtained 25 g of a viscous oil.

[0066] After dissolving the obtained viscous oil in methanol, add 50 g of silica gel (300-400 mesh) and mix well, then fully evaporate to dryness and apply the sample, and use silica gel chromatography (silica gel 300-400 mesh) for column chromatography separation. Gradient elution was performed with di...

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Abstract

The invention discloses an apixaban impurity and a synthesis method thereof. The structure of the apixaban impurity is shown as follows as described in the specification. The apixaban impurity can be used for qualitative and quantitative analysis of impurities in apixaban production, so that the quality standard of apixaban is improved, and important guiding significance is provided for safe medication.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to an apixaban impurity and a synthesis method thereof. Background technique [0002] Apixaban (Apixaban), chemical name l-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxo-1-piperidinyl)phenyl]-4 , 5,6,7-tetrahydro-1H-pyrazol[3,4-c]pyridine-3-carboxamide, the trade name is "Eliquis". A new oral factor Xa inhibitor jointly invented by Bristol-Myers Squibb and Pfizer in 2007 for the prevention of venous thromboembolism (VTE) in adult patients undergoing elective hip or knee replacement. It was officially launched in China in April 2013. Studies have shown that oral apixaban is more effective in preventing venous thromboembolism after total knee and total hip replacement and greatly reduces the risk of bleeding. It is a drug that does not need to monitor usage and dosage, has no cross-drug resistance, and has few adverse reactions. It is expected to become the first-line oral antithrombot...

Claims

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Application Information

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IPC IPC(8): C07D519/00
CPCC07D519/00
Inventor 潘斌张姗姗孙浩田于凌伟
Owner WEIFANG UNIV OF SCI & TECH
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