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Antifungal compound of substitution benzyl triazole alcohols and preparing process thereof

A kind of technology of benzylamine triazole and compound, applied in the field of medicine

Inactive Publication Date: 2006-01-11
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far there is no 1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-[N-methyl-N-(4 -Substituted amido)benzylamino]-2-propanol compounds and their antifungal activity

Method used

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  • Antifungal compound of substitution benzyl triazole alcohols and preparing process thereof
  • Antifungal compound of substitution benzyl triazole alcohols and preparing process thereof
  • Antifungal compound of substitution benzyl triazole alcohols and preparing process thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0079] Example 1: Preparation of 2-chloro-2', 4'-difluoroacetophenone (II)

[0080] 100g (0.747mol) of anhydrous aluminum oxide and 75.33g (0.667mol) of m-difluorobenzene were placed in a 500mol three-neck flask, stirred at room temperature, and 75.33g (0.667mol) of chloroacetyl chloride was slowly added dropwise, and the dropwise addition was completed Then continue to stir at room temperature for 30 minutes, slowly raise the temperature to 50°C, continue stirring at this temperature for 5 hours, pour the reaction solution into ice water as usual, precipitate crystals, and filter to obtain a solid; the filtrate is divided into two parts with 400 mL of methylene chloride The second extraction, the combined dichloromethane extracts, washed to neutral, dried over anhydrous sodium sulfate, filtered, and the solvent was recovered to obtain a solid, the solid obtained by combining two times was recrystallized with methanol to obtain 2-chloro-2',4'- Difluoroacetophenone (II) 107.38g...

Embodiment 2

[0081] Example 2: Preparation of 2-(1H-1,2,4-triazol-1-yl)-2',4'-difluoroacetophenone (III)

[0082] Triazole 27.2g (0.4mol), TEBA0.4g, anhydrous K 2 CO 3 41.56g (0.3mol) was added to 180mL of CH 2 Cl 2 A suspension was obtained in 2-chloro-2', 4'-difluoroacetophenone (II) 38.2g (0.2mol) was dissolved in 60mL CH 2 Cl 2 Add it dropwise to the above-mentioned 180mL suspension in an ice bath, and the drop is completed in about 1.5 hours. After the drop is completed, react at 0-5°C for 5 hours, and react at room temperature for 24 hours. Then filter, filter cake with CH 2 Cl 2 Wash several times, collect the filtrate, wash the filtrate 3 times with water, each 100mL, anhydrous Na 2 SO4 is dried and CH is distilled off 2 Cl 2 , dissolve the residue in 100 mL of anhydrous ethyl acetate, stir and add concentrated nitric acid dropwise until the yellow solid no longer precipitates, filter, wash the filter cake several times with a small amount of ethyl acetate, dry it, dissol...

Embodiment 3

[0083] Example 3: Preparation of 1-[2-(2,4-difluorophenyl)-2,3-epoxypropyl]-1H-1,2,4-triazole mesylate (IV)

[0084] Get 2-(1H-1,2,4-triazol-1-yl)-2',4'-difluoroacetophenone (III) 29.8g (0.115mol), trimethyl iodine oxysulfide 25.3g ( 0.115mol), 1.6g of trimethylhexadecylammonium bromide, put into a 500mL three-necked flask, add 180mL of toluene and 225mL of 20% sodium hydroxide solution (w / w), heat at 60°C for 3 hours, and the reaction is completed Finally, the toluene layer was separated, and the water layer was extracted with toluene (100mLX2). The toluene layers were combined and washed with water until neutral. 2 mL of ethyl acetate of methanesulfonic acid precipitated a pale yellow solid, which was filtered and recrystallized from methanol as usual to obtain 21.71 g of compound (IV), with a yield of 56.7% and a melting point of 128-129°C.

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Abstract

An antifungus compound 1-(1H-1,2,4-triazole-1-yl)-2-(2,4- difluorophenyl)-3-[N-methyl-N-(4-substituted amino) benzylamino]-2-propanol and its salts, and its preparing process are disclosed. Its advantages are high curative effect, low poison and broad spectrum.

Description

technical field [0001] The present invention relates to the technical field of medicine, and is a new imazodiazole antifungal compound—a substituted benzylamine triazole alcohol compound, that is, 1-(1H-1,2,4-triazol-1-yl )-2-(2,4-difluorophenyl)-3-[N-methyl-N-(4-substituted amido)benzylamino]-2-propanol compounds and their salts and preparation methods . Background technique [0002] In recent years, with the extensive application of broad-spectrum antibiotics, antineoplastic drugs, and immunosuppressants, the widespread implementation of radiotherapy and organ transplantation, the widespread development of catheters and intubations, and the rapid increase in immunocompromised patients, especially AIDS patients, have resulted in Fungal infections, especially deep fungal infections, have risen sharply, and deep fungal infections have become the main cause of death from major diseases such as AIDS and tumors. However, as far as the antifungal dr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/08A61K31/4196A61P31/10
Inventor 张万年盛春泉季海涛宋云龙姚建忠余建鑫杨松张珉朱杰
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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