A kind of preparation method of tetrabenzyl voglibose

A compound and reducing agent technology, applied in the preparation of organic compounds, amino hydroxyl compounds, sulfonates, etc., can solve the problems of potential safety hazards, the impact of voglibose purity, and the expensive sodium cyanoborohydride , to achieve the effect of improving production safety, reducing raw material costs, and being suitable for industrial production

Active Publication Date: 2017-09-05
ZEIN BIOTECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The sodium cyanoborohydride used in this method is not only expensive, but also has potential safety hazards, and also has a great impact on the purity of the final product voglibose

Method used

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  • A kind of preparation method of tetrabenzyl voglibose
  • A kind of preparation method of tetrabenzyl voglibose
  • A kind of preparation method of tetrabenzyl voglibose

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1 (1S)-(1(hydroxyl), 2,4,5 / 1,3)-2,3,4-tri-oxo-benzyl-5-[(2-hydroxyl-1-(hydroxymethyl Base) ethyl) amino] -1-carbon-benzyloxymethyl-1,2,3,4-cyclohexanetetraol benzenesulfonate (compound IV)

[0034]Add 141.0g of ketone compound I, 46.5g of serinol, and 1020mL of absolute ethanol in sequence into a 3L three-necked flask, stir, add 0.73mL of glacial acetic acid, heat in a water bath, and raise the temperature to 33-37°C. When the solid is basically dissolved, start Timing; keep warm at 33-37°C, react for about 3.0h-3.5h to obtain compound II; add 55.0g potassium borohydride several times in a small amount, after the addition is complete, control the temperature at 33-37°C, and react for 5-8h; Add 710mL of water, stir for 20-25 minutes, concentrate under reduced pressure at 40°C to remove most of the solvent, stop distillation, add 1410mL of ethyl acetate to the residue, then add 710mL of water, stir for 15-20min, separate the liquids, and keep the organic layer. E...

Embodiment 2

[0036] The preparation of embodiment 2 compound IV

[0037] Add 141.0g of Compound I, 58.1g of serinol, and 1020mL of absolute ethanol to a 3L three-neck flask in sequence, stir, add 0.73mL of glacial acetic acid, heat in a water bath, and raise the temperature to 33-37°C. When the solid is basically dissolved, start timing ; keep warm at 33-37°C, react for about 3.0h-3.5h; add 55.0g of potassium borohydride in small amounts for several times, after the addition is complete, control the temperature at 33-37°C, and react for 5-8h; slowly add 710mL of water into the reaction bottle, stir After 20-25 minutes, concentrate under reduced pressure at 40°C to remove most of the solvent, stop the distillation, add 1410mL ethyl acetate to the residue, then add 710mL water, stir for 15-20min, separate the layers, keep the organic layer, and wash the water layer with 390mL× 2 Extract with ethyl acetate, combine the organic layers, wash the organic layer with 710mL×2 purified water in turn...

Embodiment 3

[0039] The preparation of embodiment 3 compound IV

[0040] Add 141.0g of compound I, 58.1g of serinol, and 1020mL of absolute ethanol into a 3L three-necked flask in turn, stir, add 0.8mL of propionic acid, heat in a water bath, and raise the temperature to 33-37°C. When the solid is basically dissolved, start timing ; keep warm at 33-37°C, react for about 3.0h-3.5h; add 55.0g of potassium borohydride in small amounts for several times, after the addition is complete, control the temperature at 33-37°C, and react for 5-8h; slowly add 710mL of water into the reaction bottle, stir After 20-25 minutes, concentrate under reduced pressure at 40°C to remove most of the solvent, stop the distillation, add 1410mL ethyl acetate to the residue, then add 710mL water, stir for 15-20min, separate the layers, keep the organic layer, and wash the water layer with 390mL× 2 Extract with ethyl acetate, combine the organic layers, wash the organic layer with 710mL×2 purified water in turn, sepa...

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PUM

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Abstract

The invention discloses a preparing method for tetra-benzyl-voglibose, namely, (1S)-(1(hydroxyl),2,45 / 1,3)-2,3,4-trioxyl-benzyl-5-[(2-hydroxyl-1-(hydroxymethyl)ethyl)amino]-1-carbon-benzyloxy methyl-1,2,3,4-cyclohexane tetraol or benzene sulfonate thereof. The method comprises the steps that (2R, 3S, 4S, 5S)-5-hydroxyl-2,3,4-tri(benzyloxy)-5-[(benzyloxy)methyl]-cyclohexanone reacts with serinol in protonic solvent under organic acid catalysis to be prepared into an intermediate amine compound, and the intermediate amine compound is reduced to be tetra-benzyl-voglibose. The method has the advantages that reaction reagent is low in price, safety is good, solvent toxicity is low, reaction time is short, aftertreatment is simple, the product yield is large, purity is high, and the method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry and relates to a tetrabenzyl voglibose (1S)-(1(hydroxyl),2,45 / 1,3)-2,3,4-tri-oxo-benzyl Base-5-[(2-hydroxy-1-(hydroxymethyl)ethyl)amino]-1-carbon-benzyloxymethyl-1,2,3,4-cyclohexanetetraol or its benzene Process for the preparation of sulfonates. Background technique [0002] Voglibose is an α-glucosidase inhibitor used as an oral hypoglycemic agent for improving postprandial hyperglycemia in diabetes. First developed by Takeda Pharmaceutical Company of Japan, it was launched in Japan under the trade name Basen in 1994, in South Korea in 1998, and in China in 1999. [0003] Carbohydrates in food are mainly starch and sucrose, which must be hydrolyzed into monosaccharides before they can be absorbed, which depends on the action of α-glucosidase. Voglibose competes with α-glucosidase to inhibit its effect, thereby inhibiting the hydrolysis of disaccharides and delaying the absorption ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C217/52C07C213/02C07C309/29C07C303/32
Inventor 徐鹏邓祥林王飞王晓琳肖玉梅李果丰代毅谢侨罗礼平刘小伟
Owner ZEIN BIOTECHNOLOGY CO LTD
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