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Substituted triazolone benzyl amine triazole antifungal compounds and method for preparing same

A compound, the technology of triazole alcohol, applied in the field of medicine

Inactive Publication Date: 2007-03-07
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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-(2 -Report on substituted-2H-1,2,4-triazol-3-one-4-yl)benzylamino]-2-propanol compounds and their antifungal activity

Method used

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  • Substituted triazolone benzyl amine triazole antifungal compounds and method for preparing same
  • Substituted triazolone benzyl amine triazole antifungal compounds and method for preparing same
  • Substituted triazolone benzyl amine triazole antifungal compounds and method for preparing same

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Embodiment 1

[0089] Embodiment 1: the preparation of N-methyl p-nitrobenzylamine (II)

[0090] Add 700ml of saturated methylamino alcohol solution and 24g (0.14mol) of p-nitrobenzyl chloride to a 1000ml round-bottomed flask, reflux at 60°C for 5h, the reaction solution turns from green to brownish red, evaporate the solvent to dryness after the reaction, and the residue Disperse in 300ml of dilute hydrochloric acid solution and 100ml of anhydrous ether, adjust the aqueous layer to alkaline with NaOH, extract with anhydrous ether (200ml×3), combine the extracts, anhydrous Na 2 SO 4 After drying and filtering, the filtrate was evaporated to dryness to obtain 21.9 g of solid, with a yield of 92.86%.

Embodiment 2

[0091] Embodiment 2: Preparation of N-methyl-N-tert-butoxycarbonyl-4-nitrobenzylamine (III)

[0092] In a 500ml round bottom flask, add N-methyl-p-nitrobenzylamine (II) 16.7g (0.1mol) and 250mlCH 2 Cl 2 , at 0℃~5℃ (ice bath) slowly drop (BOC) 2 O 22g (0.1mol) dissolved in CH 2 Cl 2 50ml of solution. After the dropwise addition, most of the products were formed. Continue to react at room temperature for 10h, and the reaction is almost complete. Add 300ml of chloroform to dilute, wash with water (200ml×3), wash with saturated brine (200ml×3), anhydrous Na 2 SO 4 Dry, filter, and evaporate the filtrate to obtain 25 g of a brown-red liquid, with a yield of 93.4%.

Embodiment 3

[0093] Embodiment 3: Preparation of N-methyl-N-tert-butoxycarbonyl-4-aminobenzylamine (IV)

[0094] 24g (0.09mol) of compound (III), 96ml of 85% hydrazine hydrate and 300ml of absolute ethanol were placed in a 500ml round bottom flask, and a catalytic amount of active nickel was carefully added. Reflux at 75°C for 10 h. After the reaction, filter (residual nickel was treated with dilute hydrochloric acid), and the filtrate was evaporated to dryness to obtain 21.3 g of a yellow solid with a yield of 100%. Melting point: 105~107℃. It can be used in the next reaction without purification.

[0095] 1HNMR: 6.04~7.03 (4H, m, Ar-H), 4.29 (2H, s, -CH2-Ph), 3.63 (2H, br, -NH 2 ), 2.78 (3H, s, N-CH 3 ), 1.48(9H, s, -C(CH 3 ) 3 )

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Abstract

The invention relates to a substituted triazolone benzyl amine triazole antifungal compound, i.e. 1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-[N-methyl-N-(2-substituted-2H-1,2,4-triazol-3-one-4-yl) benzylaminoformyl]-2-propanols compounds, their salts and their preparation process. The compounds has very strong antimycotic effect.

Description

technical field [0001] The invention relates to the field of medical technology, and is a novel triazole alcohol antifungal compound——1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluoro Phenyl)-3-[N-methyl-N-(2-substituted-2H-1,2,4-triazol-3-one-4-yl)benzylamino]-2-propanol compounds and Its 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 drugs in clinical use are concerned, there are problems such as large side ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/12C07D403/12A61K31/4196A61P31/10
Inventor 张万年盛春泉姚建忠张珉缪震元徐辉张晶
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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