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A kind of preparation method of Miglitol

A technology of miglitol and intermediates, applied in the field of improved synthesis of miglitol, which can solve problems such as difficult procurement of raw materials, harsh reaction conditions, and cumbersome reaction steps

Active Publication Date: 2019-06-07
四川维奥制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] Although the starting materials prepared in the above methods are different, the reaction conditions are harsh, the raw materials are not easy to purchase, and the reaction steps are cumbersome.

Method used

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  • A kind of preparation method of Miglitol
  • A kind of preparation method of Miglitol
  • A kind of preparation method of Miglitol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] (1) Add glucose and ethanolamine with a molar ratio of 1:1 in the autoclave, under the catalysis of solid nickel catalyst, carry out hydrogenation reaction: temperature 85~95 ℃, pressure is 6~8MPa, stirring reaction 2~4 hours, Then concentrated to give Intermediate 1;

[0041]

[0042] According to the NMR spectrum 1 H-NMR:

[0043] δ=2.0 is the absorption peak of H in NH; δ=3.53, δ=3.37, and δ=3.38 are the absorption peaks of H in -CH-; δ=2.70, δ=2.74 are the -NH-CH in the benzene ring 2 The absorption peak of H in -; δ=3.65, δ=3.68 are -CH 2 The absorption peak of H in -; δ=2.0 is the absorption peak of H in -OH-.

[0044] (2) Biotransformation of intermediate 1 with glucobacterium oxidans, the control conditions are 12-14°C, the aeration rate is the ratio of material volume to air 1:2, the pressure is 0.1MPa, the conversion time is 48-72 hours, and the reaction is tracked by TLC When more than 90% of the conversion of intermediate 1 is completed, intermediate ...

Embodiment 2

[0053] (1) Miglitol crude product 10g and 1g activated carbon obtained in Example 1 were dissolved in 100g purified water, adjusted to pH6.5 with aqueous sodium hydroxide solution, then filtered to obtain the filtrate;

[0054] (2) Extract the filtrate obtained in step (1) with dichloromethane, wash the organic phase with water, dry the organic layer with sodium sulfate, filter, concentrate the filtrate under reduced pressure, wash the filter cake, and dry the solid obtained;

[0055](3) the dry solid of step (2) gained is joined in the mixed solvent (weight ratio is 1: 1: 0.8) in the mixed solution of 100ml ethanol, cyclohexanol, benzyl alcohol, beating at 10 ℃ for 6 hours, in Crystallize at 25°C for 8 hours, centrifuge, and dry to obtain miglitol fine product (purity 99.99%)

Embodiment 3

[0057] (1) Miglitol crude product 10g and 1g activated carbon obtained in Example 1 are dissolved in 100g purified water, and the pH is adjusted to 7.1 with ammonia, and then filtered to obtain the filtrate;

[0058] (2) Extract the filtrate obtained in step (1) with chloroform, wash the organic phase with water, dry the organic layer with sodium sulfate, filter, concentrate the filtrate under reduced pressure, wash the filter cake, and dry the solid obtained;

[0059] (3) Add the dry solid obtained in step (2) into a mixed solvent of 120ml of ethanol and tert-butanol (weight ratio is 2:0.5) and beat for 3 hours at 20°C, crystallize at 30°C for 4 hours, centrifuged and dried to obtain miglitol fine product (purity 99.98%).

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Abstract

The invention belongs to the technical field of medicine and particularly relates to a preparation method of migltol. The preparation method comprises the following steps: by taking glucose and ethanol amine as raw materials, under the conditions of hydrogen gas and high pressure, carrying out catalytic hydrogenation to prepare an intermediate hydroxyl 1; then carrying out biological oxidation conversion by using gluconic acid oxidizing bacteria to obtain an intermediate 2; carrying out catalytic hydrogenation under the conditions of hydrogen gas and high pressure to prepare a crude product of migltol; and then purifying, crystallizing and refining the crude product to obtain a finished product.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry. In particular, it relates to an improved synthesis method of miglitol. Background technique [0002] Diabetes is the most common disease caused by endocrine and metabolic disorders, and it is the second disease after cardiovascular disease. According to the WHO survey, there are hundreds of millions of diabetics in the world at present, and more than 90% of them are type 11 diabetics. With the improvement of people's living standards and nutritional structure, chronic non-communicable diseases such as diabetes are showing an epidemic trend. There are 1.2 million new diabetic patients in my country every year. [0003] Drugs for the treatment of diabetes mainly include biguanides (such as metformin), sulfonylureas (such as glipizide), glucosidase inhibitors (such as acarbose, miglitol) and thiazolidinediketone insulin Sensitizers (such as rosiglitazone), etc. Miglitol (Miglitol) i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D211/46
CPCC07D211/46
Inventor 高帆
Owner 四川维奥制药有限公司
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