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N-benzyl quinoline carboxylic acid compound, combination and preparation method thereof

A compound, benzyl technology, applied in the field of N-benzyl quinoline carboxylic acid compounds

Inactive Publication Date: 2014-01-29
SHENYANG PHARMA UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] N-benzyl quinoline carboxylic acid compounds and compositions have good aldose reductase inhibitory activity, and there is no N-benzyl Related reports on methylquinoline carboxylic acid compounds, compositions and preparation methods thereof

Method used

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  • N-benzyl quinoline carboxylic acid compound, combination and preparation method thereof
  • N-benzyl quinoline carboxylic acid compound, combination and preparation method thereof
  • N-benzyl quinoline carboxylic acid compound, combination and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0101] Preparation of 2-(6-methyl-1-benzyl-4-oxo-1,4-dihydroquinolin-3-yl)acetic acid

[0102] The title compound was prepared according to the method of the following Scheme 1

[0103] Process 1

[0104]

[0105] (i) Preparation of 3-(4-methylanilino) propionic acid

[0106] Add 21.4g (0.2mol) of p-methylaniline, 22.0g (0.22mol) of ethyl acrylate and 1.0mL of glacial acetic acid into a 250mL round bottom bottle, heat up to reflux, and stir for 15 hours. After the reaction was completed, the remaining ethyl acrylate was distilled off under reduced pressure, 100 mL of 20% aqueous sodium hydroxide solution was added to the reaction solution, and the temperature was raised to reflux and the reaction was stirred for 30 minutes. After the reaction, the reaction solution was cooled to room temperature, and an equal volume of water was added. Extract with 180ml of ethyl acetate (60mL×3), adjust the water phase to pH 6-7 with concentrated hydrochloric acid, then adjust the pH to...

Embodiment 12

[0120] Preparation of 2-(6-fluoro-1-benzyl-4-oxo-1,4-dihydroquinolin-3-yl)acetic acid (compound 12)

[0121] The title compound was prepared according to the method of the following Scheme 2

[0122] Process 2

[0123]

[0124] (i) Preparation of 3-(4-fluoroanilino) propionic acid

[0125] Add 16.65 g (0.15 mol) of fluoroaniline, 16.5 g (0.165 mol) of ethyl acrylate and 1.0 mL of glacial acetic acid into a 250 mL round bottom bottle, raise the temperature to reflux, and stir for 15 hours. After the reaction was completed, the remaining ethyl acrylate was distilled off under reduced pressure, 100 mL of 20% aqueous sodium hydroxide solution was added to the reaction solution, and the temperature was raised to reflux and the reaction was stirred for 30 minutes. After the reaction, cool the reaction solution to room temperature, add an equal volume of water; extract with 150ml ethyl acetate (50mL×3), adjust the water phase to pH 6-7 with concentrated hydrochloric acid, and th...

Embodiment 23

[0139]Preparation of 2-(6-methoxy-1-benzyl-4-oxo-1,4-dihydroquinolin-3-yl)acetic acid (compound 27)

[0140] The title compound was prepared according to the method of the following Scheme 3

[0141] Process 3

[0142]

[0143] (i) Preparation of 3-(4-methoxyanilino) propionic acid

[0144] Add 18.45 g (0.15 mol) of p-methoxyaniline, 16.5 g (0.165 mol) of ethyl acrylate and 1.0 mL of glacial acetic acid into a 250 mL round-bottomed bottle, stir and react at 50°C for 15 hours. After the reaction was completed, the remaining ethyl acrylate was distilled off under reduced pressure, 100 mL of 20% aqueous sodium hydroxide solution was added to the reaction solution, and the temperature was raised to reflux and the reaction was stirred for 30 minutes. After the reaction, the reaction solution was cooled to room temperature, and an equal volume of water was added. Extract with 150ml of ethyl acetate (50mL×3), adjust the water phase to pH 6-7 with concentrated hydrochloric acid,...

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Abstract

The invention relates to an N- benzyl quinoline carboxylic acid compound and derivatives, tautomer and salt for medical purposes, pharmaceutically acceptable solvent and combination thereof containingthe derivatives, the tautomer, the salt and the pharmaceutically acceptable solvent. The invention relates to quinoline carboxylic acid compound in general formula I and derivant, tautomer, salt formedical purposes, solvate for medical purposes and combination thereof containing the derivatives, the tautomer, the salt and the pharmaceutically acceptable solvent. The invention also relates to a preparation method of the above compounds, combination containing the compounds, applications of the compounds and the combination thereof, and intermediate compound II for preparing the compound I. The invention has simple preparation method, and the prepared compound or combination thereof in the general formula I can be used for treating and / or preventing diabetes syndrome.

Description

technical field [0001] The present invention relates to N-benzyl quinoline carboxylic acid compounds, compositions and preparation methods thereof, in particular to N-benzyl quinoline carboxylic acid compounds and their derivatives, tautomers, pharmaceutically acceptable Salts, pharmaceutically acceptable solvates, pharmaceutically acceptable compositions containing them, methods for their preparation, and uses of these compounds in medicine. The present invention also relates to methods for preparing the above compounds and their derivatives, analogs, tautomers, pharmaceutically acceptable salts, pharmaceutically acceptable solvates and pharmaceutically acceptable compositions containing them. Background technique [0002] Diabetes mellitus is a metabolic disease of multiple etiologies characterized by chronic hyperglycemia with disturbances in carbohydrate, fat and protein metabolism due to defects in insulin secretion. [0003] The treatment of diabetes itself can be we...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/233C07D215/22A61K31/47A61P3/10A61P9/00A61P13/12A61P25/00A61P9/10
Inventor 王绍杰晏菊芳李海娟
Owner SHENYANG PHARMA UNIVERSITY