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C-aryl glucoside SGLT2 (Sodium-Glucose Co-transporter 2) inhibitor

A glucopyranose, C2-C5 technology, applied in the preparation of antidiabetic drugs, in the field of type 2 sodium-glucose transporter inhibitors, can solve problems such as liver toxicity, hypoglycemia, and weight gain

Active Publication Date: 2014-04-23
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These drugs have good therapeutic effects, but there are safety problems in long-term treatment of diabetes, such as: liver toxicity, weight gain and hypoglycemia, etc.

Method used

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  • C-aryl glucoside SGLT2 (Sodium-Glucose Co-transporter 2) inhibitor
  • C-aryl glucoside SGLT2 (Sodium-Glucose Co-transporter 2) inhibitor
  • C-aryl glucoside SGLT2 (Sodium-Glucose Co-transporter 2) inhibitor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] 1-{3-[4-(2-Phenoxy)ethoxy]benzyl-4-chloro}phenyl-1-deoxy-β-D-glucopyranose (I-1)

[0085] Compound II0.1g (0.18mmol) was dissolved in DMF, followed by adding K 2 CO 3 0.05g (0.36mmol), catalytic amount of TBAB and compound III-10.072g (0.36mmol), were reacted overnight at 80°C. After the reaction, add water to dissolve potassium carbonate, extract with ethyl acetate (20mL×3), combine organic phases, wash with 1N NaOH×2, 1N HCl×2, saturated NaCl×2, anhydrous NaCl 2 SO 4 dry. Suction filtration and column chromatography separation (petroleum ether: ethyl acetate = 2:1) gave white solid IV-180 mg, yield: 66.7%.

[0086] Compound IV-180mg (0.12mmol) was dissolved in 10mL tetrahydrofuran, methanol and water (2:3:1) three-component solvent, 0.006g (0.144mmol) LiOH hydrate was added, and reacted overnight at room temperature. After the reaction was completed, it was concentrated, dissolved in ethyl acetate, and dissolved in 5% KHSO 4 × 1, washed with saturated NaCl × 1, ...

Embodiment 2

[0091] 1-{3-{4-[2-(4-Methyl)phenoxy]ethoxy}benzyl-4-chloro}phenyl-1-deoxy-β-D-glucopyranose (I- 2)

[0092] Compound II0.26g (0.47mmol) was dissolved in DMF, followed by adding K 2 CO 3 0.13 g (0.95 mmol), catalytic amount of TBAB and 0.20 g (0.95 mmol) of compound III-2 were reacted overnight at 80°C. After the reaction, add water to dissolve potassium carbonate, extract with ethyl acetate (20mL×3), combine organic phases, wash with 1N NaOH×2, 1N HCl×2, saturated NaCl×2, anhydrous NaCl 2 SO 4 dry. Suction filtration and column chromatography separation (petroleum ether: ethyl acetate = 2:1) gave white solid IV-20.16g, yield: 50%.

[0093] Compound IV-20.16g (0.234mmol) was dissolved in 10mL tetrahydrofuran, methanol and water (2:3:1) three-component solvent, LiOH hydrate 0.012g (0.281mmol) was added, and reacted overnight at room temperature. After the reaction was completed, it was concentrated, dissolved in ethyl acetate, and dissolved in 5% KHSO 4 × 1, washed with s...

Embodiment 3

[0098] 1-{3-{4-[2-(2-Methyl)phenoxy]ethoxy}benzyl-4-chloro}phenyl-1-deoxy-β-D-glucopyranose (I- 3)

[0099] Compound II0.2g (0.36mmol) was dissolved in DMF, followed by adding K 2 CO 3 0.1 g (0.72 mmol), catalytic amount of TBAB and 0.16 g (0.0.72 mmol) of compound III-3 were reacted overnight at 80°C. After the reaction, add water to dissolve potassium carbonate, extract with ethyl acetate (20mL×3), combine the organic phases, wash with 1N NaOH×2, 1N HCl×2, saturated NaCl×2, anhydrous NaCl 2 SO 4 dry. Suction filtration, column chromatography separation (petroleum ether: ethyl acetate = 2:1), to obtain white solid IV-30.21g, yield: 84%.

[0100] Compound IV-30.2g (0.29mmol) was dissolved in 10mL tetrahydrofuran, methanol and water (2:3:1) three-component solvent, 0.015g (0.348mmol) LiOH hydrate was added, and reacted overnight at room temperature. After the reaction was completed, it was concentrated, dissolved in ethyl acetate, and dissolved in 5% KHSO 4 × 1, washed w...

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PUM

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Abstract

The invention relates to the field of medicines related to diabetes mellitus and particularly relates to a 2-type sodium-glucose co-transporter (SGLT2) inhibitor with a multi-aryl glucoside structure and shown as the specification, a preparation method thereof, a medicine composition taking the compound as an active components and an application thereof in preparing medicines for resisting diabetes mellitus.

Description

technical field [0001] The invention relates to the field of medicinal chemistry related to diabetes, in particular to a type 2 sodium-glucose transporter (SGLT2) inhibitor containing a polyaryl glucoside structure that has a therapeutic effect on diabetes. The invention also discloses its preparation method and the A pharmaceutical composition in which compounds are used as active ingredients, and their application in the preparation of antidiabetic drugs. Background technique [0002] At present, there are about 370 million diabetic patients in the world, most of whom are type 2 (ie non-insulin dependent) diabetic patients. The traditional drugs for treating diabetes mainly include insulin, metformin, sulfonylureas, thiazolidinediones and α-glucosidase inhibitors. In recent years, newly listed drugs for treating diabetes include glucagon-like peptide- 1 (GLP-1) agonists, dipeptidyl peptidase-IV (DPP-IV) inhibitors, etc. These drugs have good therapeutic effects, but ther...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/10A61K31/351A61P3/10
CPCC07D309/10
Inventor 黄文龙钱海王学堃李莹杨宝卫李政
Owner CHINA PHARM UNIV
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