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Hypoglycemic drug and composition

A composition and drug technology, applied in the field of sodium-dependent glucose transporter inhibitors, can solve problems such as lactic acidosis, unsatisfactory long-term treatment, easy-induced edema and heart failure

Inactive Publication Date: 2014-09-03
北京凯利丰经贸有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to their different side effects, the above-mentioned drugs cannot meet the needs of long-term treatment.
For example, biguanide compounds can easily cause lactic acidosis; sulfonylurea compounds can cause hypoglycemia symptoms; insulin resistance improvers can easily induce edema and heart failure, and α-glucosidase inhibitors can cause abdominal pain, bloating, and diarrhea and other symptoms

Method used

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  • Hypoglycemic drug and composition
  • Hypoglycemic drug and composition
  • Hypoglycemic drug and composition

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0122] Preparation example 1: Preparation of 1-ethoxy-2-fluoro-benzene

[0123]

[0124] 2-Fluorophenol (6.7g, 60mmol) was dissolved in 66mL of acetone, iodoethane (6.3mL, 78mmol) and potassium carbonate (12.4g, 90mmol) were added, and the mixture was refluxed in an oil bath for 5 hours. Concentrate the reaction solution under reduced pressure, add 100mL ethyl acetate and 60mL water, separate the layers, extract the aqueous phase with ethyl acetate (30mL×2), combine the organic phases, dry over anhydrous magnesium sulfate, filter, and concentrate the filtrate under reduced pressure to obtain the title Product 1-ethoxy-2-fluoro-benzene (6.88 g, red oil). MS m / z(ESI): 280.2[2M+1]

preparation example 2

[0125] Preparation example 2:Preparation of (5-bromo-2-chloro-phenyl)-(4-ethoxy-3-fluoro-phenyl)methanone

[0126]

[0127] Dissolve 5-bromo-2-chloro-benzoyl chloride (12.4g, 48.8mmol) in 100mL of dichloromethane, add 1-ethoxy-2-fluoro-benzene (6.84g, 48.8mmol), cool to 0 °C, aluminum trichloride (5.86 g, 44 mmol) was added in batches, and reacted for 16 hours. Add 20 mL of 2M hydrochloric acid solution dropwise to the reaction solution under ice bath, separate the layers, extract the aqueous phase with 30 mL of dichloromethane, combine the organic phases, dry over anhydrous magnesium sulfate, filter, and concentrate the filtrate under reduced pressure to obtain the title product (5-bromo -2-Chloro-phenyl)-(4-ethoxy-3-fluoro-phenyl)methanone (12.8 g, yellow solid). MS m / z (ESI): 358.9 [M+1].

preparation example 3

[0128] Preparation example 3: Preparation of (5-bromo-2-chloro-phenyl)-(4-ethoxy-3-fluoro-phenyl)methanol

[0129]

[0130] (5-Bromo-2-chloro-phenyl)-(4-ethoxy-3-fluoro-phenyl)methanone (12.7 g, 35.5 mmol) was dissolved in 100 mL THF and methanol (v:v=1: To the mixed solvent of 1), sodium borohydride (2.68 g, 70 mmol) was added in batches under ice-cooling, and the reaction was carried out at room temperature for 30 minutes. Add 15 mL of acetone, concentrate the reaction solution under reduced pressure, add 150 mL of ethyl acetate to dissolve the residue, wash with saturated sodium chloride solution (50 mL×2), combine the organic phases, dry over anhydrous magnesium sulfate, filter, and concentrate the filtrate under reduced pressure to obtain The title product (5-bromo-2-chloro-phenyl)-(4-ethoxy-3-fluoro-phenyl)methanol (12.65 g, orange oil) was used in the next reaction without isolation.

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Abstract

The invention relates to a hypoglycemic drug and a composition, and particularly relates to a compound shown in a formula I in the specification or a solvate thereof, wherein the structure is shown in the specification. The invention further relates to a drug composition comprising the compound, and applications of the compound and the drug composition. The compound or the composition is an excellent hypoglycemic drug.

Description

technical field [0001] The present invention relates to a hypoglycemic drug and its composition, especially to the compound of formula I and its composition, and its use as a therapeutic agent, especially as a sodium-dependent glucose transporter (SGLT) inhibitor. Background technique [0002] In the early stage of diabetes treatment, diet control and exercise therapy are the first choice for blood sugar control. When these methods are difficult to control blood sugar, insulin or oral hypoglycemic drugs need to be used for treatment. At present, a variety of hypoglycemic drugs have been used in clinical treatment, including biguanide compounds, sulfonylurea compounds, insulin resistance improvers and α-glucosidase inhibitors. However, the above-mentioned drugs cannot meet the needs of long-term treatment due to their different side effects. For example, biguanide compounds can easily cause lactic acidosis; sulfonylurea compounds can cause hypoglycemia symptoms; insulin res...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H9/04C07H1/00C07D207/16A61K31/7048A61P3/10A61P27/02A61P13/12A61P5/50A61P3/06A61P3/04A61P9/10A61P9/12A61P25/00
Inventor 李友香
Owner 北京凯利丰经贸有限公司
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