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Preparation method of voglibose

A technology of voglibose and compounds, which is applied in the field of drug synthesis, can solve problems such as unfavorable industrial production, expensive palladium, and heavy metal pollution, and achieve the goals of reducing safety risks and product quality risks, excellent product quality, and reducing raw material costs Effect

Pending Publication Date: 2019-10-11
ZEIN BIOTECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The above method uses palladium, which is expensive, highly toxic, and likely to cause heavy metal pollution. At the same time, flammable and explosive hydrogen is used, which has high safety risks and is not conducive to industrial production

Method used

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  • Preparation method of voglibose
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  • Preparation method of voglibose

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1 Preparation of Voglibose (Compound II)

[0028] Put 100g of tetrabenzyl voglibose into a 3L three-necked bottle, add 1000ml of dichloromethane to dissolve, control the temperature at 15~30℃, add 180g of boron tribromide dropwise, and react for 60~90min after the completion of the reaction , control the temperature at 15~30℃, slowly add 96.7g of triethylamine dropwise, after dropping, cool down to 0~5℃, filter with suction, add 400ml 90% isopropanol to the filter cake and heat to 80~86℃ to dissolve. , naturally cooled to room temperature, suction filtered, and dried under reduced pressure at 40° C. to obtain 33 g of white solid. Yield: 77.6%, purity 99.939%, residue on ignition 0.08%.

[0029] HPLC Detection Conditions

[0030]

[0031] result:

[0032]

[0033] Detector A Ex: 350nm, Em: 430

[0034] peak number keep time area high area% Number of theoretical plates (USP) Tailing factor Resolution (USP) 1 9.573 134401 5024...

Embodiment 2

[0035] Example 2 Preparation of Voglibose (Compound II)

[0036] Take 100g of tetrabenzyl voglibose and put it into a 3L three-necked bottle, add 1200ml of tetrahydrofuran, start stirring to dissolve, control the temperature to 15~30°C, add 104g of boron trifluoride diethyl ether dropwise, dropwise, after the reaction is complete, Control the temperature at 15~30°C, add 105g of diisopropylamine dropwise, cool down to 0~5°C, filter with suction, add 450ml of 90% ethanol to the filter cake, heat to 78~85°C, keep stirring for 30~40min, cool down to 0 ~5°C, filter with suction, and dry the filter cake under reduced pressure at 40°C to obtain 35.3 g of white solid with a purity of 99.930% and a yield of 82.86%.

[0037] HPLC Detection Conditions

[0038]

[0039] result:

[0040]

[0041] Detector A Ex: 350nm, Em: 430

[0042] peak number keep time area high area% Number of theoretical plates (USP) Tailing factor Resolution (USP) 1 9.576 166339 ...

Embodiment 3

[0043] Example 3 Preparation of Voglibose (Compound II)

[0044] Take 100g of tetrabenzyl voglibose and put it into a 2L hydrogenation kettle, add 600ml of tetrahydrofuran, 600ml of methanol, 10g of 5% palladium carbon, add hydrogen until the pressure reaches 6-8kg, start stirring, and control the temperature to 15~30℃ for 24 Hours, after the reaction is complete, control the temperature at 15~30°C, add 105g of diisopropylamine dropwise, cool down to 0~5°C, filter with suction, add 450ml of 90% ethanol to the filter cake, heat to 78~85°C, keep stirring for 30 After ~40min, cool down to 0~5°C, filter with suction, and dry the filter cake under reduced pressure at 40°C to obtain 34.0g of white solid with a purity of 99.4% and a yield of 79.8%.

[0045] HPLC Detection Conditions

[0046]

[0047] result:

[0048]

[0049] Detector A Ex: 350nm, Em: 430

[0050] peak number keep time area area% Number of theoretical plates (USP) Tailing factor Resolutio...

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PUM

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Abstract

The invention discloses a preparation method of voglibose. The preparation method comprises the steps of adopting tetrabenzyl voltolose as a raw material for a reaction in an aprotic solvent in the presence of boron halide, and adding a basic substance for crystallization, suction filtration and recrystallization to obtain the high-purity and high-yield voglibose after the reaction is completed. The whole synthesis process has the advantages that the raw material cost is extremely low, the reaction time is short, and the product yield and the quality are high; the method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis and relates to a voglibose 5-(1,3-dihydroxypropan-2-ylamino)-1-(hydroxymethyl)-1,2,3,4-cyclo Preparation process of hexanethritol. Background technique [0002] Voglibose tablets were successfully developed by Takeda Corporation of Japan, and were first launched in Japan in 1994 under the trade name Basen. Voglibose is used to improve postprandial hyperglycemia in diabetes. This product is only suitable for patients who receive diet therapy and exercise therapy without significant results, or patients who take oral hypoglycemic drugs or insulin preparations in addition to diet therapy and exercise therapy without when significant results are obtained. It is contraindicated in patients with severe ketosis, diabetic coma or pre-coma, severe infection, before and after surgery, and severe trauma. The curative effect is definite, the side effect is low, and the market prospect is good. [0...

Claims

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Application Information

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IPC IPC(8): C07C213/00C07C215/44
CPCC07C213/00C07C2601/14C07B2200/07C07C215/44
Inventor 邓祥林代毅卢冲仝佳琪李大明黄超民谢乔何艳匡敏
Owner ZEIN BIOTECHNOLOGY CO LTD
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