Novel triazole antifungal compound and salt thereof

A kind of triazole compound, compound technology, application in medicine field

Inactive Publication Date: 2010-07-07
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-substituted methyl-N-( Substituted phenylalkyl)amino]-2-propanols and their antifungal activities

Method used

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  • Novel triazole antifungal compound and salt thereof
  • Novel triazole antifungal compound and salt thereof
  • Novel triazole antifungal compound and salt thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0092] Example 1: Preparation of 2-chloro-2', 4'-difluoroacetophenone (II)

[0093] Put 0.7 mol of anhydrous aluminum oxide and 0.67 mol of m-difluorobenzene in a three-necked flask, stir at room temperature, slowly add 0.67 mol of chloroacetyl chloride dropwise, continue stirring at room temperature for 30 min after the dropwise addition, and slowly heat up to 50°C, continue to stir 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, after recovering the solvent, obtains a solid, and recrystallizes the obtained solid with methanol to obtain 2-chloro - 107 g of 2',4'-difluoroacetophenone (II). The melting point is 46-47°C.

Embodiment 2

[0094] Example 2: Preparation of 2-(1H-1,2,4-triazol-1-yl)-2',4'-difluoroacetophenone (III)

[0095] Add 0.4mol of triazole, 0.4g of TEBA, and 41.56g of anhydrous potassium carbonate into 180ml of dichloromethane to obtain a suspension; dissolve 38.2g of 2-chloro-2',4'-difluoroacetophenone (II) in In 60ml of dichloromethane, add it dropwise to the above 180ml suspension under ice-bath conditions, drop it for about 1.5h, react at 0-5°C for 5h after dropping, and react at room temperature for 24h. Then filter, wash the filter cake several times with dichloromethane, collect the filtrate, wash the filtrate 3 times with water, dry, evaporate to dryness under reduced pressure, dissolve the residue in anhydrous ethyl acetate, stir and add concentrated nitric acid dropwise to a yellow solid Filter until no more precipitation occurs, the filter cake is washed several times with a small amount of ethyl acetate, and dried to obtain a crude product, which is recrystallized with n-hexane:...

Embodiment 3

[0096] Example 3: Preparation of 1-[2-(2,4-difluorophenyl)-2,3-epoxypropyl]-1H-1,2,4-triazole mesylate (IV)

[0097] Take 0.12mol of 2-(1H-1,2,4-triazol-1-yl)-2′,4′-difluoroacetophenone (III), 0.12mol of trimethyl iodine oxysulfide, trimethyldeca Put 1.6g of hexaalkylammonium bromide into a three-necked bottle, add 180ml of toluene and 250ml of 20% sodium hydroxide solution, heat at 60°C for 3 hours, separate the toluene layer after the reaction, and extract the water layer with toluene for 2 The second time, combine the toluene layers, wash with water until neutral, recover most of the toluene, dilute the residual liquid with ethyl acetate, add 2ml of ethyl acetate containing 8.4g of methanesulfonic acid dropwise at 0°C, precipitate a pale yellow solid, filter , recrystallized from methanol as usual to obtain compound (IV), with a melting point of 128-129°C.

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Abstract

The invention relates to technical field of medicine, in particular to novel azole antifungal compound and salt thereof and the application, wherein, X presents hydroxyl or straight-chain ester group or branch-chain ester group with 1-6 carbon atoms and the ester group with easily-leaving group; Y presents substituent group on aromatic ring; M presents propargyl group or cyanomethyl; P presents various substituent groups on benzene ring, the substituent positions can be different positions on aromatic ring, mono substitution, or polysubstitution combined by the substituent groups; Z presents C or N atom; if Z presents Z atom, the position can be different positions on ring, and can be mono substitution, or polysubstitution; n is equal to 0-5; the salt comprises hydrochloride, nitrate, hydrobromide or methane sulfonate. The advantages of the invention are as follows: the compound provided by the invention has strong antifungal activity, low toxicity, and wide antifungal spectrum, and can be used for preparing novel antifungal drugs.

Description

Technical field: [0001] The invention relates to the field of medical technology, and is a novel triazole antifungal compound-substituted phenylalkylamine triazole alcohol compound, that is, 1-(1H-1,2,4-triazole-1 -yl)-2-(2,4-difluorophenyl)-3-[N-substituted methyl-N-(substituted phenylalkyl)amino]-2-propanol compounds and their salts. Background technique: [0002] In the past 30 years, due to the extensive clinical application of broad-spectrum antibiotics and immunosuppressants, the increase in the number of cancer radiotherapy and organ transplantation patients, and the rapid increase in AIDS, the symbiotic relationship of normal flora in the human body has been destroyed, resulting in special fungal infections. Is the deep fungal infection rose sharply. Deep fungal infection has become one of the leading causes of death in patients with cancer and immunodeficiency diseases. However, as far as the antifungal drugs in clinical use are concerned, there are problems such ...

Claims

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Application Information

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IPC IPC(8): C07D249/08A61K31/4196A61P31/10
Inventor 周有骏唐辉朱驹吕加国郑灿辉付丙月杨辉
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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