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Quinolinone derivatives and their preparation methods and applications

A technology of quinolinone and its derivatives, which is applied in the field of quinolinone derivatives and their preparation, and can solve the problems of less research

Active Publication Date: 2016-08-24
SUZHOU HIGHFINE BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Quinoline structures exist in many drug molecules, but GPR119 agonists have less research on quinolines

Method used

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  • Quinolinone derivatives and their preparation methods and applications
  • Quinolinone derivatives and their preparation methods and applications
  • Quinolinone derivatives and their preparation methods and applications

Examples

Experimental program
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Effect test

preparation example Construction

[0018] The preparation process of quinolinone derivatives of the present invention is shown in following synthetic route:

[0019]

[0020] Among them, R means C 1 -C 4 Hydrocarbyl.

Embodiment 1

[0022] Synthetic formula III compound

[0023]

[0024] Add 10g (62.2mmol) of compound of formula II to 200mL of N,N-dimethylformamide, then add 12.88g (93.4mmol) of potassium carbonate and 7.6mL (62.2mmol) of benzyl bromide, and heat to 100°C for reaction 5 Hour. The system was poured into water, filtered, dried, and the crude product was refluxed in ethyl acetate to obtain 7.0 g of white solid, namely the compound of formula III, with a yield of 44.8%.

Embodiment 2

[0026] Synthetic formula IV compound

[0027]

[0028] 3g (11.9mmol) formula III compound, 9g (38.5mmol) p-thymphenyl bromobenzene, cuprous iodide (5.1mmol), 720mg (5.0mmol) 8-hydroxyquinoline and 4.08g (29.6mmol) potassium carbonate Dissolve in 100 mL of anhydrous dimethyl sulfoxide, under nitrogen protection, heat up to 130°C, and react for 8 hours. After the reaction was completed, it was poured into water, filtered, and the filter cake was refluxed with ethyl acetate to obtain 1.9 g of a white solid, namely compound IV, with a yield of 40%.

[0029] 1 H NMR (400MHz, CDCl 3 )δ8.18(d, J=7.9Hz, 2H), 8.09(d, J=7.9Hz, 1H), 7.59–7.31(m, 8H), 7.23(d, J=7.6Hz, 1H), 6.56( d, J=8.5Hz, 1H), 6.18(s, 1H), 5.25(s, 2H), 3.15(s, 3H).

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Abstract

The invention provides a quinolinone derivative as shown in a general formula I and a preparation method thereof, wherein R indicates C1-C4 alkyl. The invention also provides application of the quinolinone derivative as a GPR119 excitant and in preparing a drug for treating diabetes. The compound provided by the invention has certain biological activity and most importantly, the compound provided by the invention is a novel GPR119 excitant with good physicochemical properties.

Description

technical field [0001] The invention relates to the field of chemical medicines, and more particularly relates to a quinolinone derivative and its preparation method and application. Background technique [0002] Diabetes mellitus is a systemic metabolic disorder caused by absolute or relative insufficiency of insulin in the blood and decreased sensitivity of target cells to insulin. It is usually divided into two types: type I and type II. Type II diabetes accounts for more than 90% of all diabetes cases and is a serious progressive disease that causes microvascular complications (including retinopathy, neuropathy and nephropathy) and macrovascular complications (including accelerated arteriosclerosis, coronary heart disease and stroke). [0003] The treatment of type I diabetes mainly relies on insulin injection, and the development of drugs for type II diabetes is the primary task of overcoming diabetes. Defective islet β-cell function is the main cause of type II diabet...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/12A61K31/4709A61P3/10
CPCC07D401/12
Inventor 吕敏杰张海燕王桂春
Owner SUZHOU HIGHFINE BIOTECH
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