Aromatic amine ketone compounds, its synthesis method, pharmaceutical composition containing same and uses

A compound and drug technology, applied in the field of arylamine ketone compounds, can solve serious side effects and other problems

Active Publication Date: 2011-04-06
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

The currently used drugs mainly include steroidal (SAID) and non-steroidal (NSAID) anti-inflammatory drugs. Although there are many available drugs, they all have serious side effects.

Method used

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  • Aromatic amine ketone compounds, its synthesis method, pharmaceutical composition containing same and uses
  • Aromatic amine ketone compounds, its synthesis method, pharmaceutical composition containing same and uses
  • Aromatic amine ketone compounds, its synthesis method, pharmaceutical composition containing same and uses

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0115] Preparation Example 1. Preparation of 1-(4-chloro)phenyl-1-buten-3-one:

[0116] Add 8.43g of p-chlorobenzaldehyde, 60ml of acetone, and 6ml of ethanol into a 500ml beaker, add 240ml of water and 48ml of 10% sodium hydroxide aqueous solution under stirring, and gradually produce solids under rapid stirring, and the reaction is carried out at about 25°C. After checking the completion of the reaction (developing solvent: cyclohexane: ethyl acetate = 2:1), under cooling in an ice-water bath, add 6N hydrochloric acid dropwise to acidify to ph = 5-6, and then stir rapidly for 30 minutes. Let it stand at room temperature overnight, then suction filter the next day, wash the solid with a large amount of water, and dry it to obtain 10.5 g, mp.: 56-57°C, yield 96.9%. Preparation Example 2. Synthesis of 1-(4-hydroxy)phenyl-1-buten-3-one:

preparation example 2

[0117] Add 10g of 4-hydroxybenzaldehyde and 28ml of newly prepared 10% sodium hydroxide aqueous solution in a 500ml three-necked bottle, and under rapid stirring, most of the solids can be dissolved to obtain a light brown solution. After adding 20g of acetone, it becomes dark immediately Brown clear solution. Add 40ml of 10% aqueous sodium hydroxide solution, and check by TLC until the reaction is complete. Dilute with distilled water until all the solids are dissolved, add hydrochloric acid dropwise to acidify, a large amount of light yellow solids precipitate, stand for a while, then filter with suction, wash the solids with water, and after drying, wash the solids with 50% ethanol for 2 to 3 times to obtain pale yellow solids. Yellow solid, dried to obtain 11.06g, mp.: 98-101°C, yield 83.7%, recrystallized with 50% ethanol, decolorized with activated carbon, placed in refrigerator to precipitate crystals, filtered, dried to obtain light yellow crystals 9.3 g, mp: 104~105℃...

preparation example 3

[0118] Preparation Example 3. Preparation of 1-(4-methyl)phenyl-1-buten-3-one:

[0119] Dissolve 1.2g (10mmol) of 4-methylbenzaldehyde in 10ml of acetone, add 20ml of water under stirring, slowly drop into 4ml of 10% NaOH solution (internal temperature does not exceed 20°C), continue to react at room temperature for 14 hours, TLC shows that the reaction Complete, neutralized with 10% HCI to neutral, with CH 2 Cl 2 Extracted, washed with water, dried and concentrated to obtain 0.73g of light yellow viscous substance.

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Abstract

The invention provides arylamine ketone compounds having a general formula (I), the preparation of the compound, the medicinal composition containing them and the use of these compounds in preventing and / or treating platelet activating factor related diseases, especially the use in antiphlogistic immunization, in particular for treating acute or chronic inflammation, such as osteoarthritis, chronic infectious arthritis etc.

Description

technical field [0001] The present invention relates to arylamine ketone compounds represented by general formula (I), the preparation of such compounds, the pharmaceutical composition containing them and the application of such compounds in the prevention and / or treatment of diseases related to platelet activating factor, especially It is used in anti-inflammatory immunity. Background technique [0002] Rheumatoid arthritis (RA) is a worldwide chronic disease, a systemic autoimmune disease with a high incidence, long course of disease, stubborn and refractory, poor long-term curative effect, and easy to relapse, causing great pain to patients. Severe cases affect their normal work and living ability. [0003] So far, there is no ideal medicine for treating rheumatoid arthritis at home and abroad. The drugs currently used mainly include steroidal (SAID) and non-steroidal (NSAID) anti-inflammatory drugs. Although there are many available drugs, they all have serious side ef...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D295/185C07D295/10C07D211/60C07D211/32C07D241/04C07D265/30A61K31/445A61K31/495A61K9/00A61P29/00A61P19/00A61P7/02
CPCC07D317/58C07D405/06C07D211/60C07D211/14C07D295/205C07D211/22C07D211/62C07D295/185C07D241/04C07D295/108A61P19/00A61P19/02A61P19/04A61P21/00A61P29/00A61P37/08A61P43/00A61P7/02
Inventor 朱莉亚王文杰黄海洪林紫云牟丽媛聂珍贵何瑜欧阳雪宇彭珊瑛
Owner INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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