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R-lansoprazole methylamine salt compound and preparation method and pharmaceutical composition thereof

A technology of lansoprazole methylamine and compounds, applied in the field of drug synthesis, capable of solving problems such as poor stability

Active Publication Date: 2014-11-05
SHANGHAI RIGHTHAND PHARMTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The present invention aims at the problems existing in the above prior art, namely the shortcoming of the poor stability of the dexlansoprazole structure itself, provides a kind of structure such as the dexlansoprazole methylamine salt compound shown in formula 2, this compound has easy The characteristics of preparation, high purity, good stability and water solubility are superior to dexlansoprazole, which can better meet the requirements of preparations

Method used

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  • R-lansoprazole methylamine salt compound and preparation method and pharmaceutical composition thereof
  • R-lansoprazole methylamine salt compound and preparation method and pharmaceutical composition thereof
  • R-lansoprazole methylamine salt compound and preparation method and pharmaceutical composition thereof

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Experimental program
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Effect test

Embodiment 1

[0044] The preparation of dexlansoprazole methylamine salt compound:

[0045] 5g of dexlansoprazole was dissolved in 50mL of methanol solution saturated with methylamine gas in advance, and heated at 40°C to slightly reflux. In order to increase the yield and prevent methylamine from escaping, a closed system can also be used for the reaction until The reaction was complete; the temperature of the reaction solution was slowly cooled to room temperature, and then to 0° C., white needle-shaped crystals were precipitated, filtered, and dried to obtain 4.2 g of white needle-shaped crystals with a water content of 0.16%. The obtained needle-like crystals are analyzed to obtain the corresponding X-ray powder diffraction pattern, DSC spectrum and TG spectrum, respectively as image 3 , Figure 4 with Figure 5 shown.

[0046] Get the above-mentioned product and measure proton nuclear magnetic spectrum, get as follows Image 6 The hydrogen spectrum shown, 1 H-NMR (400 MHz, DMSO):...

Embodiment 2

[0051] Dissolve 5g of dexlansoprazole in a mixed solution of 25mL of ethylene glycol and 3.5g of 25% methylamine aqueous solution, heat at 50°C to slightly reflux until the reaction is complete; the reaction solution is cooled to about 10°C, and white needle-like crystals are precipitated, filtered , washed with water to remove ethylene glycol, and dried to obtain 4.92 g of white crystals with a water content of 0.30%. The obtained crystals were analyzed by H NMR spectrum to obtain the same Image 6 Consistent results are shown for the dexlansoprazole methylamine salt compound.

[0052] Changing the solvent in the above Example 2 to acetonitrile or N,N-dimethylformamide also obtained the dexlansoprazole methylamine salt compound consistent with the above.

Embodiment 3

[0054] Suspend 5g of dexlansoprazole in a two-phase mixed solution of 50mL of toluene and 5g of 25% methylamine aqueous solution, seal the reaction and stir vigorously at 30°C for 2 days to complete the reaction; cool the reaction solution to 5°C, filter the resulting white fine needles crystallized, and dried to obtain 5.05 g of white crystalline powder with a water content of 0.56%. The obtained crystals were analyzed by H NMR spectrum to obtain the same Image 6 Consistent results are shown for the dexlansoprazole methylamine salt compound.

[0055] The solvent in above-mentioned embodiment 3 is changed into ethyl acetate, also obtained the dexlansoprazole methylamine salt compound consistent with above-mentioned.

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Abstract

The invention provides an R-lansoprazole methylamine salt compound and a preparation method thereof, and absolute configuration of the molecule is determined by single crystal X-ray diffraction. Compared to R-lansoprazole, the compound has stable melting point, higher stability and greater water solubility, and is more suitable for pharmaceutical use. At the same time, the invention also provides a drug composition containing R-lansoprazole methylamine salt for the prevention and treatment of gastric acid related diseases.

Description

technical field [0001] The invention relates to a dexlansoprazole methylamine salt compound, a preparation method thereof, and a pharmaceutical composition containing it, which are used for preventing and treating gastric acid-related diseases, and belong to the technical field of drug synthesis. Background technique [0002] Dexlansoprazole (Dexlansoprazole, formula 1) is a new drug for the treatment of esophagitis developed by Japan's Takeda Pharmaceutical Company. It was approved for listing by the U.S. FDA on January 30, 2009. This drug is the monoenantiomer of the proton pump inhibitor lansoprazole Dexlansoprazole, also known as dexlansoprazole, is used to treat heartburn and different degrees of erosive esophagitis associated with non-erosive gastroesophageal reflux disease. It has higher bioavailability and Fewer side effects. [0003] [0004] The structure of dexlansoprazole shown in formula 1 is inherently unstable. Similar to esomeprazole, the chiral center in...

Claims

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Application Information

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IPC IPC(8): C07D401/12C07C209/00C07C211/04A61K31/4439A61P1/04A61P1/00A61P29/00A61P1/14A61P31/04
CPCC07D401/12
Inventor 王海平许关煜夏俊童云利彭春勇池骋
Owner SHANGHAI RIGHTHAND PHARMTECH
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