3-substituted salicylamide compound, preparation method, medicinal composition and application thereof

A technology of salicylamide and compounds, applied in the field of 3-substituted salicylamide derivatives

Inactive Publication Date: 2010-02-17
INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the above research on GK activators has made great contributions to this field, in order to improve the structure of compounds and the activity of GK activators, this field is still continuing to study

Method used

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  • 3-substituted salicylamide compound, preparation method, medicinal composition and application thereof
  • 3-substituted salicylamide compound, preparation method, medicinal composition and application thereof
  • 3-substituted salicylamide compound, preparation method, medicinal composition and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0276] Example 1.2-(3-fluorobenzyloxy)-5-benzyloxy-N-(5-methylisoxazol-3-yl)-benzamide

[0277]

[0278] Synthesis of 5-benzyloxy-2-hydroxybenzoic acid:

[0279] A DMF solution of 10ml 2,5-dihydroxygentisic acid (3.082 grams, 0.02mol) was added dropwise to 10ml of DMF suspension containing 60% NaH (1.761 grams, 0.044mol), a large amount of gas was produced, and at room temperature After stirring for 2 hours, a solution of benzyl bromide (3.421 g, 0.02 mol) in 7 ml of DMF was added dropwise to the suspension. After continuing to stir for 2-3 hours, the reaction solution was poured into 60 ml of distilled water, and the pH value was adjusted to 2 with concentrated HCL. A large amount of solids were precipitated. The solids were filtered out and recrystallized with chloroform to obtain 2.347 g of white crystals, which were recrystallized. After the mother liquor was spin-dried, 1.317 g of white crystals were obtained by solid column chromatography. 1 H-NMR (Acetone-d 6 , 30...

Embodiment 2

[0284] Example 2.2-(3-fluorobenzyloxy)-5-(4-chlorobenzyloxy)-N-(4-methylthiazol-2-yl)-benzamide

[0285]

[0286] Synthesis of 5-(4-chlorobenzyloxy)-2-hydroxybenzoic acid:

[0287] A DMF solution of 10ml 2,5-dihydroxygentisic acid (3.082 grams, 0.02mol) was added dropwise to 10ml of a DMF suspension containing 60% NaH (1.761 grams, 0.044mol), and after stirring for 2 hours, 7ml1 -Chloro-4-(chloromethyl)benzene (3.221 g, 0.02 mol) in DMF was added dropwise to the brown suspension. After 4 hours, the reaction solution was poured into 60 ml of distilled water, and the pH value was adjusted to 3 with concentrated HCL. A large amount of solids were precipitated, and the filtered solids were separated by column chromatography to obtain 3.34 g of white crystals. 1 H-NMR (Acetone-d 6 , 300M) δ5.11 (s, 2H, ph-CH 2 -O-), 6.91(d, 1H, ArH), 7.25(dd, 1H, ArH), 7.40-7.53(m, 5H, ArH), 10.68(s, 1H, OH), 12.05(s, 1H, - OH). MS FAB : (M+1) + =279

[0288] Synthesis of 2-(3-fluorobenz...

Embodiment 3

[0292] Example 3.5-(4-chlorobenzyloxy)-2-isopropoxy-N-(pyridin-2-yl)-benzamide

[0293]

[0294] Synthesis of 5-(4-chlorobenzyloxy)-2-isopropoxybenzoic acid:

[0295] Dissolve 5-(4-chlorobenzyloxy)-2-hydroxybenzoic acid (1.393 g, 5 mmol) in 30 ml DMF, add anhydrous K 2 CO 3 (1.656 g, 12 mmol), stirred at 60 °C for 1 hour, returned to room temperature, added 2-bromopropane (1.353 g, 11 mmol) dropwise to the reaction solution, stirred at 150 °C for 6 hours, then added anhydrous K 2 CO 3 (0.414 grams, 3mmol), 2-bromopropane (0.615 grams, 5mmol), stirred at 150°C for another 6 hours, stopped heating, and suction filtered after cooling down to room temperature, and the filtrate was decompressed to spin off most of the solvent to obtain a viscous liquid , add ethyl acetate and distilled water to dissolve, extract and wash with water, dry the organic layer, and spin dry the ethyl acetate to obtain about 1.5 grams of viscous, which is the crude product 5-(4-chlorobenzyloxy)-2-is...

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PUM

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Abstract

The invention discloses a 3-substituted salicylamide compound, a preparation method, a medicinal composition and application thereof, and particularly relates to 3-substituted salicylamide derivativesexpressed by a general formula I, medicinal salts thereof, hydrate and solvent compounds thereof, polycrystal and eutectic crystal thereof, precursor or derivatives thereof with the same biological function, a preparation method thereof, a composition containing one or more compounds, and application of the compounds in the aspects of treating diseases such as diabetes, obesity and the like related to glucose kinase.

Description

technical field [0001] The present invention relates to 3-substituted salicylamide derivatives represented by general formula I, their pharmaceutically acceptable salts, their hydrates and solvates, their polycrystals and cocrystals, their precursors or derivatives with the same biological function, and Its preparation method, the composition containing one or more of these compounds, and the use of these compounds in treating diseases related to glucokinase such as diabetes and obesity. Background technique [0002] Sugar is an important energy and carbon source for organisms. The decomposition of sugar produces energy, which can supply the needs of the organism's life activities, and the intermediate products of sugar metabolism can be converted into other carbon-containing compounds, such as amino acids, fatty acids, and nucleosides. Sugar metabolism can be divided into sugar decomposition and sugar synthesis. Sugar catabolism includes glycolysis, the common breakdown p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D261/14C07D277/46C07D213/75C07C235/64A61K31/625A61K31/609A61K31/612A61P3/10A61P3/04
Inventor 冯志强申竹芳李永强张宇梁黄卉环奕郭彦申褚凤鸣郭宗儒杨光中
Owner INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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