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Azole antifungal compound, its preparation method and application

A technology of a compound and a target compound, applied in the field of azole antifungal compounds and their preparation

Inactive Publication Date: 2013-07-24
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

However, during the long-term and large-scale use of the azole antifungal drugs currently used clinically, the problem of drug resistance has become increasingly prominent

Method used

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  • Azole antifungal compound, its preparation method and application
  • Azole antifungal compound, its preparation method and application
  • Azole antifungal compound, its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] Embodiment 1: Preparation of 1-ethoxyformyl-4-piperidinecarboxylic acid (2)

[0079] Add 4-piperidinecarboxylic acid (1, 10.0g, 77.4mmol), acetic anhydride (25mL, 264.5mmol), pyridine (6.3mL, 77.7mmol) into the reaction flask, and heat to reflux for 4h. Evaporate excess acetic anhydride under reduced pressure, cool to room temperature, add a mixed solvent of ethanol and ether (30mL, V / V=2:3), stir and crystallize, filter with suction, and dry to obtain white solid 1-ethoxyformyl-4 - 10.1 g of piperidinecarboxylic acid (2), yield 76%.

Embodiment 2

[0080] Embodiment 2: Preparation of 1-ethoxyformyl-4-piperidinecarbonyl chloride (3)

[0081] Add 1-ethoxyformyl-4-piperidinecarboxylic acid (2, 10.1g, 50.5mmol) and thionyl chloride (10.7mL, 201.6mmol) into an eggplant-shaped flask, stir and heat to 65°C for 4h. Thionyl chloride was distilled off under reduced pressure to obtain 10.9 g of yellow oily substance 1-ethoxyformyl-4-piperidinecarbonyl chloride (3), with a yield of 98%.

Embodiment 3

[0082] Example 3: Preparation of 2,4-difluorophenyl-(1-ethoxyformyl-4-piperidinyl)methanone (4)

[0083] Anhydrous aluminum trichloride (10.6g, 80mmol) and m-difluorobenzene (6mL, 60mol) were placed in a 100mL three-neck flask, stirred at room temperature, and slowly dropped into 1-carboethoxy-4-piperidinemethyl Acyl chloride (3, 10.9g, 19.6mmol), continue to stir at room temperature for 30 minutes after the dropwise addition, slowly raise the temperature, heat to reflux for 3h, cool to room temperature, evaporate m-difluorobenzene under reduced pressure, and pour the reaction solution as usual into 50 mL of ice water, extracted with dichloromethane (80 mL×3), combined with dichloromethane, washed with water until neutral, dried over anhydrous sodium sulfate, filtered, evaporated under reduced pressure to remove dichloromethane, and dried to obtain light yellow oil 2 , 10.7 g of 4-difluorophenyl-(1-ethoxyformyl-4-piperidinyl)methanone (4), yield 88%.

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Abstract

Belonging to the field of medical technologies, the invention provides an azole antifungal compound and its pharmaceutically acceptable salt. The structural general formula of the azole compound is shown as formula (I). The invention also provides a preparation method and application of the compound and its salt. The compound provided in the invention has good antifungal activity on various superficial and deep fungi. Compared with the antifungal drugs in current clinical application, the compound has the advantages of high efficiency, low toxicity, broad antifungal spectrum and the like, and can be used for preparation of antifungal drugs.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to an azole antifungal compound and its preparation method and application. Background technique [0002] In recent years, with the widespread application of broad-spectrum antibiotics, antineoplastic drugs, and immunosuppressants, the widespread development of peritoneal dialysis, organ transplantation, and radiotherapy, and the rapid spread of immunodeficiency diseases, especially AIDS, Candida albicans, Cryptography neoformans The incidence of opportunistic deep fungal infections such as coccus and Aspergillus fumigatus has increased dramatically. Deep fungal infection has risen to the third largest infectious disease clinically, seriously threatening human life and health. Deep fungal infections can be caused by both true pathogenic fungi and their opportunistic fungi. The former is mostly caused by external invasion through the lungs, and such diseases are rare i...

Claims

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Application Information

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IPC IPC(8): C07D401/06C07D401/14C07D405/14A61P31/10
Inventor 孙青曹永兵俞世冲柴晓云
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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