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Amino saccharide compound and preparation method and application thereof

A compound and hydrogen compound technology, which is applied in the field of amino sugar compounds and drugs for the treatment of type 2 diabetes, can solve the problems of unsimplified steps, cumbersome operation, and high cost, so as to save purification work, avoid side reactions, and be easy to operate Effect

Active Publication Date: 2020-10-09
SHANGHAI TECHWELL BIOPHARMACEUTICALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the route of this method is relatively short, its disadvantages are: cumbersome operation, many by-products; use of high-risk reagents, such as benzyl chloroformate, bromine, etc., and industrial production is also relatively difficult
The above-mentioned synthetic methods all need to protect and deprotect the hydroxyl group, the steps are long, the operation is cumbersome, and the cost is high, and the latter synthetic steps are not shortened, but in the ring-opening step, two steps of bromination ring-opening and reductive debromination are required Therefore, the steps have not been simplified, and it is still difficult to scale up production

Method used

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  • Amino saccharide compound and preparation method and application thereof
  • Amino saccharide compound and preparation method and application thereof
  • Amino saccharide compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] The preparation of compound shown in formula Ia

[0073] Add the raw material IIa (4.0g, 0.023mol) to DMF (18mL), cool to 0°C, add p-toluenesulfonic acid (4.3g, 0.025mol), after the addition is complete, naturally rise to room temperature, stir for 5h, add m-chloro Peroxybenzoic acid (m-CPBA) (6.0 g, 0.035 mol) was reacted at 40° C. for 48 h. Cool to 0°C, add Me 2 S (2.6mL, 0.035mol), after stirring for 30min, add Na 2 CO 3 (5.0g, 47.2mmol) and MgSO 4 (5.0g, 41.5mmol), stirred at room temperature for 5h, filtered with suction, washed the filter cake with methanol (10mL), evaporated the solvent under reduced pressure, then separated with UBK resin, eluted with water and 2N ammonia water in sequence, collected the eluate and concentrated , to obtain compound Ia2.9g, yield 68%.

Embodiment 2

[0075] The preparation of compound shown in formula Ia

[0076] Add raw material IIa (4.0g, 0.023mol) to methanol (30mL), cool to 0°C, add p-chlorobenzenesulfonic acid (4.8g, 0.025mol), after addition, stir at room temperature for 3h, add methyltrifluoromethane Ketone peroxide (TFDO) (5.9g, 0.046mol) was reacted at room temperature for 48h. Cool to 0°C, add Me 2 S (3.4mL, 0.046mol), after stirring for 30min, add Na 2 CO 3 (5.0g, 47.2mmol) and MgSO 4 (5.0g, 41.5mmol), stirred at room temperature for 5h, filtered with suction, washed the filter cake with methanol (10mL), evaporated the solvent under reduced pressure, then separated with UBK resin, eluted with water and 2N ammonia water in sequence, collected the eluate and concentrated , to obtain compound Ia 2.7g, yield 62%.

Embodiment 3

[0078] The preparation of compound shown in formula Ia

[0079] Add raw material IIa (4.0g, 0.023mol) to methanol (30mL), cool to 0°C, add p-toluenesulfonic acid (4.3g, 0.025mol), after the addition is complete, naturally warm to room temperature, stir for 5h, add dimethyl Ketone peroxide (DMDO) (3.4g, 0.046mol) was reacted at 50°C for 24h. Cool to 0°C, add Me 2 S (3.4mL, 0.046mol), after stirring for 1h, add Na 2 CO 3 (5.0g, 47.2mmol) and MgSO 4 (5.0g, 41.5mmol), stirred at room temperature for 5h, filtered with suction, washed the filter cake with methanol (10mL), evaporated the solvent under reduced pressure, then separated with UBK resin, eluted with water and 2N ammonia water in sequence, collected the eluate and concentrated , to obtain 3.0 g of compound Ia with a yield of 69%.

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Abstract

The invention discloses an amino saccharide compound as shown in a formula I, a preparation method of the amino saccharide compound, and an application of the amino saccharide compound in preparationof a compound as shown in a formula A.

Description

[0001] This application is a divisional application of 201610111451.1, the filing date of the original application is February 29, 2016, and the title of the invention is "amino sugar compound, its preparation method and use". technical field [0002] The invention relates to the field of drug synthesis, in particular to a class of amino sugar compounds, a preparation method of the amino sugar compound, and the use of the amino sugar compound to prepare drugs for treating type 2 diabetes. Background technique [0003] Diabetes mellitus is a metabolic disorder characterized by chronic hyperglycemia caused by various etiologies, accompanied by abnormal sugar, fat and protein metabolism caused by defects in insulin secretion or action. The main clinical symptoms of the disease are "three excesses and one deficiency", that is, polydipsia, polyphagia, polyuria, and weight loss. Type 2 diabetes, also known as adult-onset diabetes, mostly occurs after the age of 35-40, accounting f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C215/44C07C213/00
CPCC07C213/00C07C2601/14C07C215/44Y02P20/55
Inventor 胡杨唐志军何兵明季晓铭
Owner SHANGHAI TECHWELL BIOPHARMACEUTICALS CO LTD
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