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Carbon glucoside sodium glucose transport protein body 2 inhibitor

A technology of glucose transport and carbon glycosides, which is applied in the field of chemical medicine, can solve problems such as vomiting, short plasma half-life, and side effects, and achieve the effects of low side effects, strong hypoglycemic effect, and prolonged action time

Active Publication Date: 2018-07-17
JIANGSU TASLY DIYI PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, existing compounds also have some deficiencies when increasing drug efficacy and enhancing stability, such as short plasma half-life, not long hypoglycemic action time, vomiting, diarrhea and other side effects that need improvement.

Method used

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  • Carbon glucoside sodium glucose transport protein body 2 inhibitor
  • Carbon glucoside sodium glucose transport protein body 2 inhibitor
  • Carbon glucoside sodium glucose transport protein body 2 inhibitor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0092] Synthesis of 5-bromo-2-chlorobenzoyl chloride (2)

[0093] 60.00 g (0.26 mol) of 5-bromo-2-chlorobenzoic acid (1) was added to 200 mL of dry dichloromethane, 1.5 mL (5.2 mol) of DMF was added dropwise, and four times were added to the reaction solution under ice-salt bath conditions. Slowly drop 32 mL (0.39 mmol) of oxalyl chloride into the mixture, and the temperature of the reaction solution is required to be between 0 and 5 °C. After the dropping is completed, the reaction solution is slowly raised to room temperature for 12 h. The reaction was monitored by thin-layer chromatography (TLC), until the reaction of the raw materials was completed, the solvent and oxalyl chloride were evaporated under reduced pressure, and the oxalyl chloride was evaporated three times with dichloromethane. m / z):255.1[M+H]+

Embodiment 2

[0095] Synthesis of 5-bromo-2-chloro-4'-methoxybenzophenone (3)

[0096] 34.10g (0.26mol) of anhydrous aluminum trichloride was added to dry 110mL of dichloromethane in three batches under ice-bath conditions, and 23mL (0.22mol) of anisole was slowly added dropwise to the reaction solution after stirring for 15min. The rate of addition makes the temperature of the reaction solution at 0 to 5° C. After 30 min, the dichloromethane (115 mL) solution of Intermediate 2 (66g) is slowly added dropwise to the reaction solution, and the rate of addition is controlled to keep the temperature of the reaction solution at 0 to 5° C. After dripping, the reaction was carried out in an ice bath for 4h. Raised to room temperature for 6h. After the reaction was completed, the reaction solution was slowly poured into 750 mL of ice water, stirred for 45 min, and the organic layer was separated, washed with 1 mol·L-1 aqueous sodium hydroxide solution, 2 mol·L-1 hydrochloric acid, and saturated br...

Embodiment 3

[0098] Synthesis of 5-bromo-2-chloro-4'-methoxydiphenylmethane (4)

[0099] Under stirring conditions, 5mL (0.31mol) of triethylsilane and 5.5g of 3 (0.17mol) were added to 20mL of a 1:2 mixture of dichloromethane and acetonitrile for reaction, and the temperature was controlled at 10 °C and slowly added 2.5mL of boron trifluoride ether solution, with the reaction proceeding, the reaction temperature was controlled not to exceed 20°C. The reaction was monitored by HPLC. If the reaction was not completed, the reaction was stirred overnight, and 0.5 mL of triethylsilane and 0.3 mL of boron trifluoride ether solution were added, and then the reaction temperature was raised to 50 °C and the reaction was stirred for 4 h. After cooling, the reaction was stopped with 5 mL of 7N KOH solution, the aqueous phase was extracted with dichloromethane (2×), the organic phases were combined, washed with 2N KOH and saturated brine (2×) successively, dried over anhydrous sodium sulfate, filtere...

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Abstract

The invention relates to a carbon glucoside sodium glucose transport protein body 2 inhibitor, a preparation method and an application of the inhibitor. The carbon glucoside sodium glucose transport protein body 2 inhibitor has a structure as shown in general formula (I) as shown in the specification.

Description

technical field [0001] The invention relates to the field of chemical medicines related to diabetes, in particular to a sodium-glucose transporter type 2 (SGLT-2) inhibitor with a carbon glycoside sodium-glucose transporter body structure. The invention also discloses its preparation method and use. Background technique [0002] Diabetes mellitus is a metabolic disorder syndrome characterized by hyperglycemia caused by defective insulin secretion and / or insufficient insulin action. It is divided into two types: type 1 (T1DM) and type 2 (T2DM). - Cells cannot produce enough insulin (absolute insulin deficiency), mostly in adolescents, the latter is due to insufficient insulin secretion or insulin resistance (relative insulin deficiency), more common in middle-aged and elderly people. [0003] Sodium-dependent glucose transporters (SGLTs) rely on the electrochemical potential of sodium ions to actively transport extracellular glucose into the cytoplasm. SGLT2 is a low-affini...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/10A61K31/351A61P3/10
CPCC07D309/10C07B2200/07A61K31/351A61P3/10Y02P20/55
Inventor 王国成汪国松
Owner JIANGSU TASLY DIYI PHARMA CO LTD
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