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Sulfonic acids, their derivatives and pharmaceutical compositions containing them

A technology of sulfonic acids and compounds, applied in the field of sulfonic acids and their derivatives and pharmaceutical compositions containing them

Inactive Publication Date: 2008-03-05
DOMPE FARM SPA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, the novel R and S-2-phenylpropanoic acids have recently been recognized as potent IL-8 inhibitors, completely free from undesired COX inhibition (PCT / EP02 / 12939)

Method used

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  • Sulfonic acids, their derivatives and pharmaceutical compositions containing them
  • Sulfonic acids, their derivatives and pharmaceutical compositions containing them
  • Sulfonic acids, their derivatives and pharmaceutical compositions containing them

Examples

Experimental program
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Effect test

preparation example Construction

[0163] Preparation of E-arylene sulfonic acid (sodium salt)

[0164] Arylethanesulfonic acid was dissolved in thionyl chloride (5 mL), and the resulting solution was refluxed overnight. After cooling at room temperature, thionyl chloride was evaporated in vacuo, and the crude arylethanesulfonyl chloride was diluted with dry THF (5 mL), cooled in an ice-water bath at 0°C; 1N NaOH aqueous solution (0.64 mmol) was added at 4°C; the ice-water bath was removed, The reaction mixture was left standing for about 1 hour, and the temperature was raised to room temperature, resulting in the precipitation of a white solid. The organic sodium salt was vacuum filtered, washed with THF, and dried in a vacuum oven at 40° C. to obtain pure E-arylene sulfonic acid sodium salt (0.32-0.51 mmol) as a white powder (50-80% yield ).

[0165] Following the method described above, the following compounds were prepared:

[0166] E-2-(4-isobutylphenyl)ethylenesulfonic acid sodium salt (10)

[0167]...

Embodiment 3

[0175] A General Synthesis Method for E-Arylethene Sulfonamides

[0176] Arylethanesulfonic acid (0.64 mmol) was dissolved in thionyl chloride (5 mL), and the resulting solution was refluxed overnight. After cooling at room temperature, thionyl chloride was evaporated in vacuo, and the crude arylethanesulfonyl chloride was diluted with dry THF (5 mL), cooled in an ice-water bath at 0 °C; the selected amine (1.28 mmol) was added dropwise. The ice-water bath was removed, and the reaction mixture was allowed to stand until the temperature rose to room temperature. After complete disappearance of the starting reagent, the solvent was evaporated in vacuo, and chloroform (10 mL) and water (10 mL) were added to the residue; the two phases were separated by shaking, and the organic phase was washed with water (3×15 mL), dried over sodium sulfate, and evaporated in vacuo , the crude product was obtained, which was purified by flash chromatography to isolate pure E / Z-arylethenesulfon...

Embodiment 4

[0214] A General Synthesis of Aryl Methanesulfonamides

[0215] (1-Methyl-5-isobutyrylpyrrolyl)-1-methanesulfonamide (30)

[0216] Starting from the commercially available reagent methyl 1-methyl-2-pyrrole acetate, it undergoes Friedel Crafts acylation with isobutyryl chloride to give (1-methyl-5-isobutyrylpyrrolyl)-1- formyl acetate, thus synthesizing the compound. The ester group is then hydrolyzed. According to the experimental procedure described in WO02 / 0704095, the related sodium salt of (1-methyl-5-isobutyrylpyrrolyl)-1-methanesulfonate was obtained.

[0217] (1-Methyl-5-isobutyrylpyrrolyl)-1-methanesulfonic acid sodium salt (0.64 mmol) was dissolved in thionyl chloride (5 mL), and the resulting solution was refluxed overnight. After cooling at room temperature, thionyl chloride was evaporated in vacuo, and the crude (1-methyl-5-isobutyrylpyrrolyl)-1-methanesulfonyl chloride was diluted with dry THF (5 mL), cooled in an ice-water bath at 0°C; dropwise into Ammonia...

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Abstract

Selected sulfonic acids, their derivatives and pharmaceutical compositions containing such compounds are useful in inhibiting the chernotactic activation of neutrophils (PMN leukocytes) induced by the interaction of Interleukin-8 (IL-8) with CXCRI and CXCR2 membrane receptors. The compounds are used for the prevention and treatment of pathologies deriving from said activation. Notably, the selected sulfonic acids and their derivativas are devoid of cyclo-oxygenase inhibition activity and are particularly useful in the treatment of neutrofil-dependent pathologies such as psoriasis, ulcerative colitis, melanoma, chronic obstructive pulmonary disease (COPD), bullous pemphigoid, rheumatoid arthritis, idiopathic fibrosis, glomerulonephritis and in the prevention and treatment of damages caused by ischemia and reperfusion.

Description

technical field [0001] The present invention relates to sulfonic acid and its derivatives and pharmaceutical compositions containing them. The compounds and compositions can be used to prevent and treat tissue damage caused by malignant aggregation of polymorphonuclear neutrophils (PMN leukocytes) at inflammatory sites. Background of the invention [0002] Specific blood cells (macrophages, granulocytes, neutrophils, polymorphonuclear cells) respond to a chemical stimulus by migrating along a concentration gradient of the chemical stimulus through a process called chemotaxis (when called chemotaxis). When stimulated by the substance of chemical factor). Major well-known stimulators or chemokines are represented by breakdown products of complement C5a, lysed from bacterial surfaces or some N-formyl peptides derived from synthetic peptides, such as formyl-methionyl-leucyl-phenylalanine Acid (f-MLP), mainly various cytokines, including interleukin-8 (IL-8, also known as CXCL8)...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C309/24C07C309/29C07C311/16C07C311/21C07D207/263C07D207/333A61K31/18A61K31/10A61P29/00C07C309/65C07C309/73C07C311/08C07C311/13C07C311/27C07C311/35C07C311/51C07D207/26C07D207/27C07D207/32
CPCC07C309/73C07C311/35C07C311/51C07D207/333C07C311/08C07C309/24C07D207/27C07C311/13C07C309/65C07C311/27A61P1/04A61P11/00A61P13/12A61P17/00A61P17/06A61P29/00A61P35/00A61P43/00A61P9/10
Inventor M·阿莱格蒂A·阿拉米尼M·C·切斯塔R·贝尔蒂尼C·比蕯里F·科洛塔
Owner DOMPE FARM SPA
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