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Benzyl aralkyl ether compounds, method for preparing same, intermediate compounds, use of said compounds, method for treatment and/or prevention, pharmaceutical composition and medicament containing same

A technology of benzyl aralkyl ethers and compounds, which can be applied in the directions of drug combination, drug delivery, antipyretic drugs, etc., can solve the problems of reducing effectiveness and the like

Inactive Publication Date: 2012-08-01
BIOLAB SANUS FARMACEUTICA LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0025] Interestingly, prolonged and repeated exposure of fungal strains to antifungal drugs may cause these strains to resist the effects of these drugs, reducing their effectiveness

Method used

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  • Benzyl aralkyl ether compounds, method for preparing same, intermediate compounds, use of said compounds, method for treatment and/or prevention, pharmaceutical composition and medicament containing same
  • Benzyl aralkyl ether compounds, method for preparing same, intermediate compounds, use of said compounds, method for treatment and/or prevention, pharmaceutical composition and medicament containing same
  • Benzyl aralkyl ether compounds, method for preparing same, intermediate compounds, use of said compounds, method for treatment and/or prevention, pharmaceutical composition and medicament containing same

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Experimental program
Comparison scheme
Effect test

preparation example Construction

[0125] The preparation method can generally be expressed by the following process 1:

[0126]

[0127] Wherein Ar, R of formula (II) and (III) 1 -R 6 , n and m are as defined in the detailed description of formula (I), and wherein X refers to a unit selected from Cl, Br, I, MS (mesylate) and TS (tosylate).

[0128] (process 1)

[0129] Advantageously, the derivative 1-[2-(2,4-dichlorophenyl)-2-{[4-(trifluoromethyl)benzyl]oxy}ethyl]-1H-imidazole according to the invention ( BL-123) can be prepared from 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)alcohol and 1-(chloromethyl)-4-(trifluoromethyl)benzene as follows Reaction preparation (Procedure 2).

[0130]

[0131] (process 2)

Embodiment 1

[0134] Suspend 10.30 g of compound 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl) alcohol in 26 mL of acetone, then add 31 mL of 50% sodium hydroxide solution in water, followed by More than 26 mL of acetone, keeping the entire reaction mixture under vigorous stirring. Then 0.45 g of triethylbenzyl ammonium chloride was added and the reaction mixture was kept at reflux for 30 min. Still under reflux, 8.2 g of 1-(chloromethyl)-4-(trifluoromethyl)benzene compound (diluted in 13 mL of acetone) were added, and stirring and reflux were maintained for 6 hours. Finally, the heterogeneous mixture is filtered and the phases are separated. The organic phase was rotary evaporated to dryness at 45 °C. The resulting residue was dissolved in 100 mL of cold diethyl ether. Then 2 mL of nitric acid (65%) was added at 0° C. and stirring was maintained for 1 hour. Finally, the product was filtered and washed with cold ethanol and dried at 65°C for 12 hours. The product (compound BL123) obtaine...

Embodiment 2

[0136]Compound 1-(2,4-dichlorophenyl)-2-(1H-imidazole-1- base) ethanol (5.14 g) in anhydrous THF (52 mL). Then, a solution (3.6 mL) containing compound 1-(chloromethyl)-4-(trifluoromethyl)benzene in anhydrous THF (10 mL) was slowly added to the reaction mixture, keeping the reaction mixture under reflux for 3 Hour. At the end of this time, 50 mL of water was added, and the product was extracted with ethyl acetate, dried over magnesium sulfate, and the final solvent was rotovapped. The residue obtained after complete evaporation of the solvent was dissolved in diethyl ether (20 mL) and cooled to 0°C. 65% nitric acid (1.4 mL) was gently added to the solution of the residue. Then, the product was filtered and dried at 65°C. The pure product was obtained after recrystallization from methanol. The product (compound BL123) obtained as a white solid has the following characteristics: 1H NMR (300 MHz-DMSO): 9.05 (1H, s), 7.72 to 7.74 (1H, m), 7.65 to 7.66 (4H, m), 7.53 to 7.54 (...

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Abstract

The present invention describes new anti-fungal, benzyl aralkyl ether compounds of formula (I), where: Ar stands for aryl, imidazolyl, 1,2,4-triazolyl, benzimidazolyl; R1, R2, R4 and R5 independently stand for hydrogen, halogen, C1-6 alkyl; R3 stands for halogen, C1-6 alkyl or O-R', where R' stands for hydrogen or lower alkyls; R6 stands for aryl, substituted aryl, trifluoromethyl, trichloromethyl or O-R', where R' stands for hydrogen or lower alkyls, the aryl substituents being a halogen or a tetrazolyl radical; n and m independently equal an integer from 0 to 5, provided that, when Ar stands for imidazolyl, R3 for chlorine, R6 for p-phenyl and R1, R2, R4 and R5 for hydrogen, n is different from 2. When n and m differ from 0 and 1, R3 or R6 may represent optionally different substituents. The present invention also relates to the pharmaceutically acceptable salts, solvates, pro-drugs, esters, enantiomers and / or diastereoisomers thereof, or mixtures thereof, to the methods for preparing said compounds, to intermediate compounds, to pharmaceutical compositions comprising said compounds and / or derivatives, to medicaments comprising said compounds and / or derivatives, as well as to the uses of and methods using said compounds and / or derivatives for the treatment and / or prevention of conditions and / or diseases caused by micro-organisms such as fungi, bacteria and / or protozoa, for inhibiting the proliferation and / or survival of said micro-organisms, for treating and / or preventing micro-organism growth on an individual, and for producing a medicament.

Description

technical field [0001] The present invention relates to compounds as the aralkylbenzyl ethers described in formula (I), their enantiomers, their diastereoisomers, their prodrugs, esters, their pharmaceutically acceptable salts, their Pharmaceutically acceptable solvates and / or mixtures of these compounds and / or derivatives in any proportion, relating to methods for preparing these compounds, intermediate compounds, pharmaceutical compositions containing such compounds and / or derivatives, Medicines comprising said compounds and / or derivatives, as well as the use of these compounds and / or derivatives for the treatment and / or prevention of conditions and / or diseases caused by microorganisms (such as fungi, bacteria and / or protozoa), for For inhibiting the proliferation and / or survival of said microorganisms, for treating and / or preventing colonization of microorganisms in individuals and for the preparation of medicaments. [0002] The present invention also relates to the use o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/56C07D257/06A61K31/4174A61K31/4196C07C15/14A61P31/04A61P31/10A61P33/02
CPCC07D403/12A61K9/0014A61K47/14C07D233/54C07D233/22C07C22/08C07D249/08A61K31/4174A61P1/02A61P1/04A61P11/00A61P13/12A61P15/00A61P17/00A61P17/14A61P25/00A61P27/02A61P29/00A61P31/00A61P31/04A61P31/06A61P31/10A61P33/00A61P33/02A61P35/00A61P7/00A61P9/00Y02A50/30
Inventor A·F·开普勒S·L·萨克瑞M·H·扎伊姆C·E·D·C·图扎瑞姆
Owner BIOLAB SANUS FARMACEUTICA LTD
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