3-substituted piperazine triadimenol antifungal compounds and their salts

A technology of triazole and compound, applied in the field of medicine, can solve the problems of narrow antibacterial spectrum, large toxic and side effects, increase of drug-resistant strains and the like

Inactive Publication Date: 2004-12-29
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

However, currently commonly used clinical antifungal drugs such as amphotericin B (Amphotericin B), ketoconazole (Ketoconazole), fluconazole (Fluconazole) and itraconazole (Itraconazole) have large toxic and side effects, narrow antibacterial spectrum, resistance The increasing number of drug strains and other issues

Method used

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  • 3-substituted piperazine triadimenol antifungal compounds and their salts
  • 3-substituted piperazine triadimenol antifungal compounds and their salts
  • 3-substituted piperazine triadimenol antifungal compounds and their salts

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0104] 1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-[4-(2-furoyl)piperazine]-2- Preparation of Propanol (Compound 1 in Table 1)

[0105] Take 1.65 g (5 mmol) of 1-[2-(2,4-difluorophenyl)-2,3-epoxypropyl]-1H-1,2,4-triazole methanesulfonate (III), 1.08g (6mmol) of 2-mercaptopyridine, 2.07g (15mmol) of anhydrous potassium carbonate and 0.1g of phase transfer catalyst hexadecyltrimethylammonium bromide, 30ml of dimethylformamide, in an oil bath at 90-95°C The reaction was heated and stirred for 8 hours. Cool, add 50ml of water under stirring, extract with ethyl acetate (3×70ml), wash with water (30ml×3), anhydrous Na 2 SO 4 Dry, recover the solvent, and recrystallize from absolute ethanol to obtain 1.76 g of a white solid with a melting point of 123-5° C. and a yield of 84.4%.

[0106] 1 H-NMR (DMSO-d 6 )δ, ppm: 8.24 (1H, s, triazole C 3 -H), 7.82 (1H, s, triazoleC 5 -H), 6.77~8.30 (6H, m, Ar-H), 5.10 (1H, s, OH), 4.49-4.58 (2H, AB system, triazole-CH 2 ), 3.33-3.35...

Embodiment 2

[0109] 1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-[4-(2-(1,2,4-triazole- 1-yl) acetyl) piperazine] -2-propanol (compound 12 in table 1) preparation

[0110] Take 1.65 g (5 mmol) of 1-[2-(2,4-difluorophenyl)-2,3-epoxypropyl]-1H-1,2,4-triazole methanesulfonate (III), 2-(1,2,4-triazol-1-yl) acetylpiperazine 1.17g (6mmol), anhydrous potassium carbonate 2.07g (0.015mol) and phase transfer catalyst cetyltrimethylammonium bromide 0.1 g, 25ml of dimethylformamide, heated and stirred in an oil bath at 90-95°C for 8 hours. Cool, add 50ml of water under stirring, extract with ethyl acetate (60ml×3), combine the extracts, wash with water (25ml×3), anhydrous Na 2 SO 4 After drying, filtering, and recovering the solvent, the crude product was obtained, and the crude product was subjected to column chromatography, and the 3 : C 2 h 5 Eluted with OH=9:1, 1.72 g of a light yellow solid was obtained, with a melting point of 121-2°C and a yield of 79.6%.

[0111] 1 H-NMR (DMSO-d ...

Embodiment 3

[0114] 1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-[4-(4-(2-pyridinemethoxy)phenyl ) piperazine] the preparation of -2-propanol (compound 16 in table 1)

[0115] Take 1.65 g (5 mmol) of 1-[2-(2,4-difluorophenyl)-2,3-epoxypropyl]-1H-1,2,4-triazole methanesulfonate (III), 4-(4-(2-pyridylmethoxy)phenyl)piperazine 1.62g (6mmol), anhydrous potassium carbonate 2.07g (0.15mol) and phase transfer catalyst cetyltrimethylammonium bromide 0.1g , 25ml of dimethylformamide, heated and stirred in an oil bath at 90-95°C for 8 hours. Cool, add 50ml of water under stirring, extract with ethyl acetate (60ml×3), combine the extracts, wash with water (25ml×3), anhydrous Na 2 SO 4 After drying, filtering, and recovering the solvent, the crude product was obtained, and the crude product was subjected to column chromatography, and the 3 : C 2 h 5 Eluted with OH=9:1, 1.32 g of a yellow solid was obtained, with a melting point of 142-4° C. and a yield of 52.2%.

[0116] 1 H-NMR (DMSO-d ...

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Abstract

The present invention relates to medicine technology, and is 3-substituted piperazine triazonyl alcohol as new antifungal compound and its salt. The substituting radical may be in any position of heterocycle, and the compound may be single or multiple substituted. The said compound may form salt with several kinds of organic and inorganic acid. The present invention exhibits very powerful antifungal activity and may be used in preparing antifungal medicine.

Description

technical field [0001] The invention relates to the technical field of medicine, and is a novel 3-substituted piperazine triazole antifungal compound 1-(1H-1,2,4-triazol-1-yl)-2-(2,4- Difluorophenyl)-3-substituted piperazinyl-2-propanol compounds and salts thereof. Background technique [0002] In the past three decades, due to the extensive use of broad-spectrum antibiotics in clinical practice, the increase in the number of patients with cancer radiotherapy, chemotherapy and organ transplantation, the widespread use of corticosteroids and immunosuppressants, and the prevalence of AIDS, the rate of deep fungal infection has increased by 40%. times. The latest statistics show that 60% of the direct cause of death among AIDS patients is deep fungal infection. Deep fungal infection is increasingly becoming a common and frequently-occurring disease, and has become one of the main causes of death in patients with cancer and immunodeficiency diseases....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/4196A61P31/10C07D249/08C07D401/12C07D407/12C07D417/12
Inventor 刘超美何秋琴姜远英曹永兵梁爽门秀峰
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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