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A kind of preparation method of tagagliflozin

A tepagliflozin and compound technology, which is applied in the field of medicine, can solve the problems of prolonging the synthetic route and containing, and achieve the effects of stable properties, shortened synthetic route, and less total impurities

Active Publication Date: 2021-08-20
GUANGZHOU LIXIN PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In this synthetic route, although the first 3 steps can obtain the tipagliflozin that can obtain higher yield, but because adopt anisole and aluminum trichloride to debenzylate in step 3, and intermediate 2 is easy to because bound The effect of the gram reaction makes the product contain specific impurities, so steps 4 and 5 are required for acetylation and deacetylation to be removed, and finally further recrystallization to obtain a purified product, so the synthetic route is greatly extended

Method used

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  • A kind of preparation method of tagagliflozin
  • A kind of preparation method of tagagliflozin
  • A kind of preparation method of tagagliflozin

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0039] Embodiment 1, a kind of preparation method of tepagliflozin

[0040] Include the following steps:

[0041] S1. Compound N-10-a preparation of

[0042] Take 112g of compound N-9 (0.347mol, 1.25eq) and stir with 720ml of anhydrous tetrahydrofuran, replace with nitrogen three times, lower the temperature and control the temperature at -80°C to -75°C, add dropwise 240ml of 1.6M n-butyllithium n-hexane solution ( 0.347mol, 1.25eq), the dropping time is 2h, after the dropping is completed, keep stirring for 1h; continue to control the temperature at -80°C~-75°C, add dropwise the tetrahydrofuran solution of compound N-8 (120g compound N-8 (0.277mol, 1.0eq) was dissolved in 240ml tetrahydrofuran), the dropping time was 2h, after the dropping was completed, it was incubated and stirred for 2h until the reaction was monitored by TLC (petroleum ether: ethyl acetate = 6:1 was used as the developer, and the reaction occurred when there was no compound N-8 Completely); temperatur...

Embodiment 2～3

[0049] Embodiment 2~3, a kind of preparation method of tepagliflozin

[0050] The difference from Example 1 is that the amount of raw materials used in Examples 2-3 is different, see Table 1 for details.

[0051] Table 1

[0052]

[0053]

[0054] The preparation method is similar to Example 1.

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Abstract

The invention belongs to the technical field of medicine, and in particular relates to a preparation method of tepagliflozin. Taggliflozin of the present invention reacts compound N-10-a by compound N-9, n-butyllithium and compound N-8, and then adds triethylsilane and boron trifluoride ether to react to obtain compound N-11, Then add Lewis acid reaction derived. The preparation method of the present invention shortens the synthesis route of tepagliflozin, and the obtained tepagliflozin has a high net yield, less impurity content and stable properties.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a preparation method of tepagliflozin. Background technique [0002] Diabetes is a metabolic disease characterized by hyperglycemia due to insulin secretion defects or insulin action disorders. The drugs in the prior art are mainly based on the source of blood sugar or / and the whereabouts of blood sugar. For example, insulin is Treatment is carried out through the above two entry points at the same time. But the fact is that in addition to the above two entry points, the kidney also plays an important role in the regulation of blood sugar. Studies have shown that 180g of glucose is filtered from the glomerulus every day, but it is completely reabsorbed by the renal tubules, so there is no glucose in the urine. Sugar, urine sugar is negative; when the blood sugar concentration exceeds 11mmol / L, too much glucose is filtered out from the glomerulus, which exceeds the r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D309/10
CPCC07D309/10
Inventor 高悦译卢江陈成斌刘恩桂张倩
Owner GUANGZHOU LIXIN PHARM CO LTD
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