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Application of piperidyl-containing pyranone compound in preparation of fungal infection resisting drugs

A compound, pyrone technology, applied in the field of medicine, can solve the problems of poor bioavailability, low water solubility, inconvenient use for patients, etc., achieve huge social and economic benefits, and inhibit the growth of fungi.

Inactive Publication Date: 2013-04-17
DALI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the biggest problem facing echinocandycin is: there is no oral dosage form, only limited to injection (and limited to hospital use), so it is quite inconvenient for patients to use
Although the new product has an expanded antibacterial spectrum, it has poor metabolic properties and physical and chemical properties, low water solubility, and poor bioavailability; patients need a high-fat diet to facilitate drug absorption, or take expensive special preparations to take effect; in order to increase water solubility The added cyclodextrin also poses a greater threat to those with renal insufficiency

Method used

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  • Application of piperidyl-containing pyranone compound in preparation of fungal infection resisting drugs
  • Application of piperidyl-containing pyranone compound in preparation of fungal infection resisting drugs
  • Application of piperidyl-containing pyranone compound in preparation of fungal infection resisting drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1: Preparation of compounds of formula (1)

[0018] 1.1 Instruments and Reagents

[0019] The melting point was measured by a micro melting point apparatus (produced by Beijing Tektronix), and the temperature was not corrected; the optical rotation was measured on a Polax-2L automatic polarimeter made in Japan; the IR was measured by a Bruker Vector-22 infrared spectrometer, and was pressed by KBr; UV Spectra were measured with a Shimadzu UV-240 UV spectrophotometer; 1H NMR 1 H NMR, carbon nuclear magnetic resonance spectroscopy 13 C NMR and 2D NMR were measured by INOVA superconducting nuclear magnetic resonance spectrometer (VARIAN INOVA-400MHz) (tetramethylsilyl ether TMS as the internal standard); electrospray mass spectrometry ESI-MS was measured by Bruker Esquire3000+ mass spectrometer, column chromatography was used Silica gel (100-200, 200-300 and 300-400 mesh) and silica gel GF254 (10-40 mesh) for thin layer chromatography are products of Qingdao Oce...

Embodiment b

[0040] Example b: Fungal inhibitory activity test of the compound of formula (1)

[0041] Referring to the standardized antifungal susceptibility test method proposed by the National Committee for Clinical Laboratory Standards (NCCLS), the compound 3-[(1-benzyl-piperidin-4-ylamino) of formula (1) prepared in Example 1 was tested - In vitro antifungal activity of methyl]-6-(2-bromo-4,5-dimethoxy-phenyl)-2H-pyran-2-one.

[0042] 2.1 Fungal standard strain:

[0043] Candida albicans ATCC10231: provided by Chongqing Center for Disease Control;

[0044] Candida albicans ATCC76615: Provided by Changzheng Hospital Affiliated to Second Military Medical University.

[0045] 2.2 Reagents:

[0046] 2.2.1 Sabouraud dextrose agar: a product of Guangdong Kai Microbial Technology Co., Ltd.

[0047] 2.2.2 Yeast extract: subpackaged by Haishenggong Bioengineering Technology Service Co., Ltd.

[0048] 2.2.3 Triazamorpholinopropanesulfonic acid (3-N-morpholinopropanesulfonicacid, MOPS). ...

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Abstract

The invention relates to application of a piperidyl-containing pyranone compound in preparation of fungal infection resisting drugs and particularly discloses a substituted pyranone compound 3-[(1-benzyl-piperidin-4-ylamino)-methyl]-6-(2-bromo-4,5-dimethoxy-phenyl)-2H-pyran-2-one or pharmaceutically acceptable salts thereof and a preparation method and medicinal application thereof. The in-vitro fungal growth inhibition activity of the compound is determined through a micro-dosage liquid-based dilution method; and shown by experimental results, the 80% inhibition concentration of the substituted pyranone compound to the growth inhibition of candida albicans is 125 micrograms / milliliter. Shown by pharmacodynamic results, the compound or pharmaceutically acceptable salts thereof can be expected to be applied to drugs for prevention and treatment of diseases caused by fungal infection.

Description

technical field [0001] The present invention relates to the technical field of medicine, in particular to a substituted pyrone compound 3-[(1-benzyl-piperidin-4-ylamino)-methyl]-6- Use of (2-bromo-4,5-dimethoxy-phenyl)-2H-pyran-2-one in the preparation of antifungal infection medicaments. Background technique [0002] With the development of medical science, various new drugs and technologies such as broad-spectrum antibiotics, hormones, various catheter intubation techniques, chemotherapy, transplantation and other medical means are widely used, as well as HIV infection and tumors, resulting in the gradual weakening of the human immune system. The cases of destruction are increasing year by year, resulting in an increasing incidence of deep fungal diseases; on the other hand, with the abuse of antibiotics and the widespread use of clinical antifungal drugs, traditional antibiotics are not effective against some serious fungal infections and Bacterial infections and fungal ...

Claims

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Application Information

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IPC IPC(8): A61K31/453A61P31/10C07D405/12
Inventor 杜一民陶晶卜绍先杨增福黄照昌赵昱李辉
Owner DALI UNIV
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