Substituted hydroxylamine derivatives with anti-inflammatory activity and preparation method and application thereof

A technology of substituents and representatives, applied in the field of substituted hydroxylamine derivatives with anti-inflammatory activity, their preparation and application, and able to solve problems such as application limitations

Active Publication Date: 2010-08-18
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the application of NSAIDs is limited due to its side effects on the gastrointestinal tract (GI) and kidneys, especially the "Vanlo incident" that occurred in 2004, which has aroused people's attention to the safety of NSAIDs

Method used

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  • Substituted hydroxylamine derivatives with anti-inflammatory activity and preparation method and application thereof
  • Substituted hydroxylamine derivatives with anti-inflammatory activity and preparation method and application thereof
  • Substituted hydroxylamine derivatives with anti-inflammatory activity and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] 1-Phenyl-3-thiosemicarbazide

[0071] Phenylhydrazine hydrochloride (6.0g, 0.042mol) was suspended in 40ml of absolute ethanol, 0.5ml of concentrated hydrochloric acid was added dropwise, the temperature was raised to about 40°C, KSCN (4.9g, 0.050mol) was added in batches for 40min, and the temperature was raised to reflux for 6h. After suction filtration, the filtrate was allowed to stand still, and a large amount of precipitate was precipitated, and then suction filtration gave 4.5 g of white powder, yield: 65.2%, m.p.197-200°C.

Embodiment 2

[0073] p-methylsulfonylbenzoyl chloride

[0074] p-Methanesulfonylbenzoic acid (10 g, 0.05 mol) was suspended in SOCl 2 (25ml, 0.21mol), heated and refluxed for 2.5h, concentrated to dryness under reduced pressure to obtain a white yellowish solid, which was recrystallized from toluene to obtain 8.5g of white solid, yield: 78%, m.p.128-130°C.

Embodiment 3

[0076] 2-(4-Methanesulfonylbenzoyl)-2-phenyl-thiosemicarbazide

[0077] Suspend 1-phenyl-3-thiosemicarbazide (0.6g, 3.6mmol) in 20ml of anhydrous acetone, add triethylamine 5d, stir at room temperature, add p-methylsulfonylbenzoyl chloride (0.79g , 3.6mmol), heated to reflux for 3h, suction filtered, and the filter cake was dried to obtain 1.1g of white solid, yield: 87.8%, m.p.204-206°C.

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Abstract

The invention relates to the field of pharmaceutical chemistry, in particular to substituted hydroxylamine derivatives. The invention also discloses a preparation method for the substituted hydroxylamine derivatives, a medicinal composition comprising the compounds, and the application of the compounds in treating rheumatoid arthritis and osteoarthritis, and treating other diseases and symptoms through doubly inhibiting cyclooxygenase-2(COX-2) and 5-lipoxygenase (5-LOX).

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a class of substituted hydroxylamine derivatives. The invention also discloses a preparation method of these substituted hydroxylamine derivatives, a pharmaceutical composition containing the compound and the use of the compound in treating rheumatoid arthritis , osteoarthritis and in the treatment of other diseases or conditions by dual inhibition of cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX). Background technique [0002] Non-steroidal anti-inflammatory drugs (NSAIDs) are one of the most widely used drugs in the world. They are the basic symptomatic drugs for the treatment of rheumatic diseases. and soft tissue inflammation. However, the application of NSAIDs is limited due to its side effects on the gastrointestinal tract (GI) and kidneys, especially the "Vanlo incident" in 2004, which aroused people's concern on the safety of NSAIDs. Therefore, the development of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/12A61K31/4196A61P29/00A61P19/02A61P19/08
Inventor 徐进宜吴晓明江波黄晓静蒋婧章朱培清柳军黄婧儿王秋娟蒋斯怡
Owner CHINA PHARM UNIV
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