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Triazole alcohol derivative, preparation method and application thereof

A kind of technology of triazole alcohol and triazole, applied in the field of medicinal compounds

Active Publication Date: 2015-08-05
YANGTZE RIVER PHARM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far there is no relevant 2-(2,4-difluorophenyl)-3-(1-substituted-1H-1,2,3-triazol-4-yl)-1-(1H-1,2 , 4-triazol-1 base)-2-propanol compounds and their antifungal activity

Method used

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  • Triazole alcohol derivative, preparation method and application thereof
  • Triazole alcohol derivative, preparation method and application thereof
  • Triazole alcohol derivative, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] Example 1: (2R*,3S*)-2-(2,4-difluorophenyl)-3-methyl-1-(1H-1,2,4-triazol-1-yl)- Synthesis of 4-pentyn-2-ol

[0083] Step 1: Synthesis of 3-butyn-2-ol mesylate

[0084] Dissolve 3-butyn-2-ol (25g) in dichloromethane, add triethylamine (99mL), add methanesulfonyl chloride (41mL) dropwise at -78 degrees, after the reaction is complete, pour 200mL of bicarbonate In sodium aqueous solution, extracted twice with dichloromethane, the organic phase was washed twice with water, dried with anhydrous sodium sulfate, spin-dried and used directly in the next step.

[0085] NMR data: 1 H NMR (300MHz, CDCl 3 )δ5.29(q,1H),3.13(s,3H),2.71(s,1H),1.66(d,3H).

[0086] Step 2: Synthesis of (2R*,3S*)-1-chloro-2-(2,4-difluorophenyl)-3-methyl-4-pentyn-2-ol

[0087] Pd(CH 3 EN) 2 Cl 2 Dissolve in tetrahydrofuran, add triphenylphosphine, add 2-chloro-2',4'-difluoroacetophenone and 3-butyn-2-ol methanesulfonate after reacting for 10 minutes, then slowly add di The toluene solution of eth...

Embodiment 2

[0091] Example 2: (2R*,3S*)-2-(2,4-dichlorophenyl)-3-methyl-1-(1H-1,2,4-triazol-1-yl)- Synthesis of 4-pentyn-2-ol

[0092] Step 1: Synthesis of (2R*,3S*)-1-chloro-2-(2,4-dichlorophenyl)-3-methyl-4-pentyne 2-ol

[0093] Pd(CH 3 EN) 2 Cl 2 Dissolve in tetrahydrofuran, add triphenylphosphine, add 2-chloro-2',4'-dichloroacetophenone and 3-butyn-2-ol mesylate after reacting for 10 minutes, then slowly drop di The toluene solution of ethyl zinc was poured into the hydrochloric acid solution after reacting at room temperature for 1 hour, extracted 3 times with ethyl acetate, the organic phase was washed twice with saturated aqueous sodium chloride solution, dried by anhydrous sodium sulfate and then spin-dried to obtain ( 2R*,3S*)-1-Chloro-2-(2,4-dichlorophenyl)-3-methyl-4-pentyn 2-ol crude. used directly in the next step.

[0094] Step 2: (2R*,3S*)-2-(2,4-dichlorophenyl)-3-methyl-1-(1H-1,2,4-triazol-1-yl)-4 -Synthesis of pentyn-2-ol

[0095] Dissolve 1H-1,2,4-triazole in DMS...

Embodiment 3

[0097] Example 3: (2R*,3S*)-2-(2,5-difluorophenyl)-3-methyl-1-(1H-1,2,4-triazol-1-yl)- Synthesis of 4-pentyn-2-ol

[0098] Step 1: Synthesis of (2R*,3S*)-1-chloro-2-(2,5-difluorophenyl)-3-methyl-4-pentyne 2-ol

[0099] Pd(CH 3 EN) 2 Cl 2 Dissolve in tetrahydrofuran, add triphenylphosphine, add 2-chloro-2', 5'-difluoroacetophenone and 3-butyn-2-ol mesylate after reacting for 10 minutes, then slowly add di The toluene solution of ethyl zinc was poured into the hydrochloric acid solution after reacting at room temperature for 1 hour, extracted 3 times with ethyl acetate, the organic phase was washed twice with saturated aqueous sodium chloride solution, dried by anhydrous sodium sulfate and then spin-dried to obtain ( 2R*,3S*)-1-Chloro-2-(2,5-difluorophenyl)-3-methyl-4-pentyn 2-ol crude. used directly in the next step.

[0100] Step 2: (2R*,3S*)-2-(2,5-difluorophenyl)-3-methyl-1-(1H-1,2,4-triazol-1-yl)-4 -Synthesis of pentyn-2-ol

[0101] Dissolve 1H-1,2,4-triazole in DMS...

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Abstract

The invention relates to a triazole alcohol derivative, a preparation method and application thereof. The triazole alcohol derivative is a 2-(2, 4-difluorophenyl)-3-(1-substituted-1H-1, 2, 3-triazole-4-yl)-1-(1H-1, 2, 4-triazole-1yl)-2-propanol compound. The invention also provides a salt of the compound, a pharmaceutical composition, a preparation method and application thereof. The compound provided by the invention has strong antifungal activity, and has the advantages of low toxicity, broad antibacterial spectrum and the like, and can be used for preparation of antifungal drugs.

Description

technical field [0001] The invention relates to the technical field of medical compounds, in particular to a novel triazole alcohol derivative and its preparation method and application. 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 effects, narrow antibacterial spectrum, and easy drug resistance. Effective antifungal drugs, especially anti-deep fungal drugs, ...

Claims

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Application Information

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IPC IPC(8): C07D249/08C07D401/14C07D403/14A61K31/4196A61K31/4439A61K31/506A61P31/10
CPCC07D249/08A61K31/4196A61K31/4439A61K31/506C07D401/14C07D403/14
Inventor 张大志姜远英倪廷峻弘蔡瞻由守谊仰振球齐东绮
Owner YANGTZE RIVER PHARM GRP CO LTD
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