Empagliflozin monocrystalline and preparation method and purpose thereof

A technology of empagliflozin and single crystal, which is applied in the field of empagliflozin single crystal and its preparation, can solve the problems that the preparation method of empagliflozin single crystal needs to be improved, and achieve good shape, good reproducibility, and guaranteed The effect of accuracy

Inactive Publication Date: 2017-01-11
WATERSTONE PHARMA WUHAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, at present, empagliflozin single crystal and its preparation method still need to be improved

Method used

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  • Empagliflozin monocrystalline and preparation method and purpose thereof
  • Empagliflozin monocrystalline and preparation method and purpose thereof
  • Empagliflozin monocrystalline and preparation method and purpose thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1 The synthesis of empagliflozin crude product

[0041] According to the following steps to synthesize the crude product of Empagliflozin, the specific synthesis method is as follows:

[0042] Step 1 synthesizes 2,3,4,6-tetra-O-trimethylsilyl-D-gluconolactone, the specific method is as follows:

[0043] (1) Add 800 grams of tetrahydrofuran, 100 grams of gluconolactone, and 454 grams of N-methylmorpholine to the reaction flask at room temperature. Under nitrogen protection, start to add 366 grams of trimethylchlorosilane dropwise. After the reaction is complete, Add ice water to quench the reaction.

[0044] (2) Add 2.6 kg of purified water and 500 g of n-heptane to the reaction solution in step (1), stir, leave to stand and separate the layers, and separate the organic layer.

[0045] (3) Wash the organic layer with 1.5 kg of 5% sodium dihydrogen phosphate aqueous solution, 1.5 kg of purified water and 1.5 kg of sodium chloride solution respectively.

[00...

Embodiment 2

[0061] Embodiment 2 Preparation of Empagliflozin Single Crystal

[0062] Weigh 0.20 g of the crude product of Empagliflozin prepared in Example 1, add 20 ml of crystallization solvent methanol, and wait until the product is completely dissolved, use the solvent slow evaporation method, set the temperature at 10-20°C, and cultivate for 20 days, colorless flakes Crystals are precipitated, and the crystals are ggliflozin single crystals, the yield of the ggliflozin single crystals is 80%, and the purity is 99.6%. Using X-ray powder diffractometer to detect, Empagliflozin single crystal X-ray powder diffraction pattern is as follows figure 1 shown.

Embodiment 3

[0063] Example 3 Preparation of Empagliflozin Single Crystal

[0064] Weigh 0.20 g of the crude product of Empagliflozin prepared in Example 1, add 20 ml of crystallization solvent ethanol, wait until the product is completely dissolved, use the solvent slow evaporation method, set the temperature at 10-20 °C, and cultivate for 25 days, there are colorless flakes Obtained by microscope observation, the crystal is Ggliflozin single crystal, the yield of Ggliflozin single crystal is 84%, and the purity is 99.5%. Using X-ray powder diffractometer to detect, Empagliflozin single crystal X X-ray powder diffraction pattern as figure 1 shown.

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PUM

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Abstract

The invention relates to an Empagliflozin monocrystalline and a preparation method and a purpose thereof. A chemical structural formula of Empagliflozin is shown as a formula I, according to the Empagliflozin monocrystalline, the X-ray powder diffracting at the diffraction angles 2theta of 13.33, 14.66, 18.81, 20.33, 23.44, and 26.84 has characteristic peaks. A crystal structure of the Empagliflozin monocrystalline is a monoclinic system, the space group is C2, the number Z of molecules in crystal is 4, and the Empagliflozin monocrystalline is colorless sheet-shaped crystallization at normal temperature. The monocrystalline form is good, and the purity is as high as 99%.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular, the invention relates to a single crystal of empagliflozin and its preparation method and application. Background technique [0002] Empagliflozin (compound represented by formula I) is a SGLT2 (sodium-glucose co-transporter 2) inhibitor, jointly developed by Boehringer Ingelheim and Eli Lilly, and was approved by FDA in August 2014 listed. For the treatment of type 2 diabetes in adult patients. [0003] [0004] Sodium-glucose cotransporter 2, expressed in the proximal renal tubules, is responsible for the reabsorption of glucose filtered through the lumen of the renal tubules. Empagliflozin increases urinary glucose excretion by inhibiting SGLT2, reducing the reabsorption of filtered glucose and lowering the renal glucose threshold (RTG). Current evidence suggests that SGLT2 inhibitors have a range of effects on glycemic control, including weight loss and modest reductions...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D407/12A61K31/351A61P3/10
CPCC07D407/12
Inventor 徐助雄孙梦颖崔健钱丽娜
Owner WATERSTONE PHARMA WUHAN
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