Aryl, heteroaromatic and bicyclic aryl nitrone compounds, prodrugs and pharmaceutical compositions of the same to treat human disorders

A compound, heteroaryl technology, applied in the direction of active ingredients, applications, animal repellants, etc. of heterocyclic compounds

Inactive Publication Date: 2008-02-13
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, based on the antioxidant activity of nitrones, diseases previously reported to be sensitive to antioxidant therapy or related to the production of free radicals may be sensitive to nitrone treatment

Method used

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  • Aryl, heteroaromatic and bicyclic aryl nitrone compounds, prodrugs and pharmaceutical compositions of the same to treat human disorders
  • Aryl, heteroaromatic and bicyclic aryl nitrone compounds, prodrugs and pharmaceutical compositions of the same to treat human disorders
  • Aryl, heteroaromatic and bicyclic aryl nitrone compounds, prodrugs and pharmaceutical compositions of the same to treat human disorders

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0561]

[0562] N-(tert-butyl)-C-[2-(methoxycarbonyl)phenyl]nitrone (1)

[0563] A mixture of commercially available methyl 2-formylbenzoate (100 mg, 0.61 mmol) and N-(tert-butyl)hydroxylamine hydrochloride (109 mg, 0.732 mmol) in methanol (5 mL) was stirred at ambient temperature for 24 hours. The mixture was then concentrated in vacuo and the resulting crude product was dissolved in ethyl acetate (15ml) and extracted with water (2 x 20ml). Using Na 2 SO 4 After drying the combined organic layers and concentrating in vacuo, chromatography on silica gel afforded compound 1 (10 mg, 20%). MS: m / z 236 (MH+).

Embodiment 2

[0566]

[0567] N-Cyclohexyl-C-[2-(methoxycarbonyl)phenyl]nitrone (2)

[0568] Using N-cyclohexylhydroxylamine hydrochloride and methyl 2-formylbenzoate as raw materials, compound 2 was prepared according to the procedure described in Example 1. MS: m / z 262 (MH+).

Embodiment 3

[0570]

[0571] N-Benzyl-C-[2-(methoxycarbonyl)phenyl]nitrone (3)

[0572] Compound 3 was prepared according to the procedure described in Example 1 using N-benzylhydroxylamine hydrochloride and methyl 2-formylbenzoate as raw materials. MS: m / z 270 (MH+).

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Abstract

Disclosed are aryl, heteroaromatic and bicyclic aryl nitrone compounds and pharmaceutical compositions containing such derivatives. The disclosed compositions are useful for preventing and/or treating pain, neurodegenerative, autoimmune and inflammatory diseases or conditions in mammals.

Description

[0001] This application claims priority to US Provisional Application Nos. 60 / 492,488, 60 / 492,489, and 60 / 492,490, filed August 4, 2003, the entire contents of which applications are incorporated herein by reference. 1. Field of invention [0002] The present invention relates to aryl, heteroaryl and bicyclic aryl nitrone compounds and their use as therapeutic agents to treat conditions associated with inflammation in mammals, including but not limited to: arthritis, such as but not limited to Pascal Neurodegenerative diseases of Kinson's and Alzheimer's disease, stroke, uveitis, asthma, myocardial infarction, treatment and prevention of pain syndromes (acute and chronic or neuropathic pain), traumatic brain injury, acute spinal cord injury, alopecia (hair loss), inflammatory bowel disease and autoimmune diseases. 2. Background of the invention [0003] Arthritis and related inflammatory disease symptoms come in more than 100 different forms, including rheumatoid arthritis (...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/24A61K31/34A61K31/13A61K31/15A01N33/02C07C29/04
Inventor 迈克尔·G·凯利萨加纳雷亚纳·加纳哥尼雷温德拉·B·阿帕萨尼
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