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Hydroxy diphenyl ether compound

A technology of hydroxydiphenyl ether and compound, which is applied in the field of hydroxydiphenyl ether compound and can solve the problems of reducing the long-term effect of antibacterial treatment materials and the like

Inactive Publication Date: 2006-03-29
CIBA SPECIALTY CHEM HLDG INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For some industrial applications, this effect is undesirable, because this slow release effect also reduces the long-term effect of antimicrobial treatment materials such as textiles, paper, plastics, cellulose sponges, etc.

Method used

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  • Hydroxy diphenyl ether compound
  • Hydroxy diphenyl ether compound
  • Hydroxy diphenyl ether compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0231] The first reaction step of the reaction scheme:

[0232]

[0233] Put a mixture of 6.1g (0.05mol) 2,5-dimethylphenol, 2.8g (0.05mol) KOH, 0.4g (0.006mol) copper powder and 50g (0.25mol) bromoanisole in a dehydrator Heat to 160°C in a standard reaction apparatus and keep for 5 hours. After cooling, the reaction mass was suspended in toluene and filtered. The product of formula (101a) is isolated by distillation at 125 °C / 1 Pa (0.01 mbar) after distilling off the solvent and excess reagents. A colorless oil was obtained which slowly crystallized at room temperature. Yield: 4.6 g (40%).

[0234] The second reaction step of react filing:

[0235]

[0236] 4.6 g (0.02 mol) of 4-(2,5-dimethylphenoxy)-methoxybenzene and 30 ml of HBr (47% in water) were heated under reflux in 100 ml of acetic acid for 4 hours. After cooling, the acetic acid was distilled off, and the resulting reaction product was dissolved in 100 ml of dichloromethane, washed with 200 ml of water, a...

Embodiment 2

[0238] The first reaction step of the reaction scheme:

[0239]

[0240] Add acid chloride (57.25 mmole), toluene (250 ml) and activated zinc (57.24 mmole) into a three-necked flask equipped with an overhead stirrer and a condenser. The mixture was stirred at room temperature (30° C.) for 15 minutes. A solution of m-phenoxyphenol (4.5g, 24.2m mole) in toluene (150ml) was added and the reaction mixture was stirred at 70-75°C for 30 minutes. Thin layer liquid chromatography (TLC) analysis indicated no more starting material. The reaction mixture was cooled to room temperature, then filtered. The organic layer was washed with 2 x 100 ml of an aqueous solution of potassium carbonate (20%) followed by water. After drying with anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to obtain O-acyl compound with a yield of 85%.

[0241] The second reaction step of the reaction scheme:

[0242]

[0243] Mix O-acetate (16m mole) and aluminum trichlori...

Embodiment 3

[0248] Agar incorporation assays were performed to determine the MICs of the various compounds shown in Table 1

[0249] medium:

[0250] Nutrient agar, as test agar for bacteria

[0251] Mueller hinton agar for aerobic bacteria

[0252] Müller-Hinton broth is used to obtain microbial suspensions

[0253] Ethanol, as a solvent

[0254] Wilkins-Chalgren agar for aerobic bacteria

[0255] Sabouraud's dextrose agar for the cultivation of dermatophytes.

[0256] Examples of test bacteria:

[0257] Staphylococcus aureus ATCC 6538

[0258] Human Staphylococcus DSM 20330

[0259] Escherichia coli NCTC 8196

[0260] Pseudomonas aeruginosa CIP A-22

[0261] Candida albicans ATCC 10231

[0262] Aspergillus niger ATCC 6275

[0263] experiment method:

[0264] The test substances are dissolved in ethanol and a series of diluted solutions of the compound of formula (102) in agar are prepared.

[0265] Anaerobic bacteria and dermatophytes were activated on agar plates and washe...

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Abstract

The present invention relates to the use of hydroxydiphenyl ether compounds as antimicrobially active substances, to certain new compounds of this type and to processes for the preparation of these compounds.

Description

technical field [0001] The present invention relates to the use of hydroxydiphenyl ether compounds as antimicrobial active substances, certain novel compounds of this type and processes for the preparation of such compounds. Background technique [0002] It is known that certain halogenated diphenyl ether compounds have excellent antibacterial activity. Compounds of this type are therefore widely used, for example, as active substances for the antibacterial treatment of pharmaceuticals and household goods, additives for detergents and in the hygiene sector, for example for soaps or dental hygiene products. Compounds of this type are described in German Patent 2538016. However, it would be desirable to be able to provide a class of non-halogenated highly effective antimicrobials. Polymeric materials can be antimicrobially treated by incorporating halogenated diphenyl ether compounds, the active substances being constantly migrated to the surface of ...

Claims

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Application Information

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IPC IPC(8): A61K31/075A61K8/34A61Q11/00C11D3/48A01N31/14A61K8/30A01N31/16A01N35/04A61K8/00A61K8/35A61K31/085A61K31/11A61K31/12A61P1/02A61P17/00A61P17/16A61P31/04A61Q5/00A61Q5/02A61Q15/00A61Q17/00A61Q19/00A61Q19/10C07B61/00C07C41/16C07C41/18C07C43/23C07C43/295C07C45/46C07C45/54C07C45/67C07C47/575C07C49/84C11D7/26C11D7/32D06M13/02D06M13/152
CPCC11D7/263A61Q19/10A61K8/35Y10S514/88A01N31/16Y10S514/901A01N35/04A61Q11/00C07C49/84C07C45/54C07C45/673A61Q15/00Y10S514/881C07C43/295C07C47/575A61Q5/02A61K8/347C11D7/3227C07C45/46C11D3/48A61Q17/005A61P1/02A61P17/00A61P17/16A61P31/04A61K31/085
Inventor W·赫尔兹尔W·哈尔普D·奥克斯K·普克特勒M·施奈德S·U·库尔卡尼A·S·拉德哈克里斯纳M·S·萨旺特A·B·马特雷
Owner CIBA SPECIALTY CHEM HLDG INC
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