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Novel medical uses of aporphine alkaloid and derivative thereof

A technology of alkaloids and derivatives, which is applied in the pharmaceutical composition of pharmaceutical active ingredients, aporphylloid alkaloids and their derivatives, and application fields in the development of antifungal drugs, so as to reduce adverse reactions, increase efficacy, and reduce The effect of dosage

Inactive Publication Date: 2009-04-15
成都军区昆明总医院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But there is no patent document related to the antifungal effect of aporphi-type alkaloids and their derivatives

Method used

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  • Novel medical uses of aporphine alkaloid and derivative thereof
  • Novel medical uses of aporphine alkaloid and derivative thereof
  • Novel medical uses of aporphine alkaloid and derivative thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0021] Example 1: Extraction and separation of monomeric alkaloids 1-III from Huangteng.

[0022] Take 50 kg of fresh yellow vine (Fibraurea recisa Pierre.), crush it, add 10 times the amount of chloroform, stir and extract at room temperature for 6 hours, filter, and recover the solvent from the filtrate under reduced pressure to obtain 470 g of yellow extract.

[0023] Dissolve this extract in an appropriate amount of acetone and adsorb it on about 600g of diatomaceous earth, separate it by 5000g silica gel column chromatography, and use cyclohexane-ethyl acetate (100:0-100:30) gradient elution, each fraction accepts 1000mL. The solvents of each fraction were recovered under reduced pressure, and after checking by thin-layer chromatography (TLC), similar fractions were appropriately combined. The combined fractions with antifungal activity were purified by repeated silica gel column chromatography and Sephadex HL-20 chromatographic column separation (methanol or acetone elu...

example 2

[0024] Example 2: Physicochemical and Spectroscopic Data of Monomeric Compounds.

[0025] Romer's base: pale yellow blocky crystal (cyclohexane), potassium iodide reagent reaction is positive, melting point mp81 ~ 82 ℃. MS m / z 279 (M + ), 243, 219. 1 H-NMR (CDCl 3 , δ): 6.56 (1H, s, 3-H), 2.72~3.20 (a total of 7H, m, 4, 5, 7-H 2 , 6a-H), 2.61 (3H, s, N-CH 3 ), 5.93, 6.08 (each 1H, s, -OCH 2 O-), 7.21-7.34 (3H, m, 8, 9, 10-H), 8.07 (1H, d, J=8.4Hz, 11-H). 13 C-NMR (CDCl3 , δ): 142.6 (s, C-1), 146.7 (s, C-2), 107.4 (d, C-3), 126.6 (s, C-3a), 29.1 (t, C-4), 53.5 (t, C-5), 62.0 (d, C-6a), 34.6 (t, C-7), 135.4 (s, C-7a), 127.3 (d, C-8), 127.5 (d, C- 9), 128.2(d, C-10), 128.6(d, C-11), 131.1(s, C-11a), 116.4(s, C-1a), 126.9(s, C-1b), 100.7( t,-OCH 2 O-), 43.8 (q, N-CH 3 ).

[0026] 8-Hydroxyromer's base: Light yellow blocky crystals (methanol), positive for potassium iodide reagent, melting point 219.0-221.0°C. MS m / z295 (M + ), 265, 169, 114. 1 H-NMR (CDCl 3 , δ): 6....

example 3

[0028] Example 3 Antifungal activity of aporphyrin alkaloids in vitro

[0029] 1. Experimental materials

[0030] 1.1 Test drug

[0031] 8-Hydroxyromer's base, Stephanine, romer's base: monomeric compounds extracted and isolated from Huangteng.

[0032] Fluconazole: Shaanxi Zhonglin Pharmaceutical Co., Ltd., batch number 20070309.

[0033] Dimethyl sulfoxide: Shanghai Chemical Reagent Co., Ltd., batch number W20040422.

[0034] 8-Hydroxyromer's base, stepherine, and romer's base were prepared with dimethyl sulfoxide to a concentration of 2560 μg / ml, and fluconazole was prepared with sterile water for injection to a concentration of 64 μg / ml. Store at 20°C. Before the experiment, the drug was taken out in a 40°C water bath to melt, mixed well, and the pharmacodynamic test was carried out respectively.

[0035] 1.2 Experimental strains

[0036] Candida albicans strains: standard strain (ATCCY0109) provided by the Second Military Medical University, clinical strains (28, 94...

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Abstract

The invention relates to new medical application of aporphine alkaloid and the derivatives as shown in constitutional formula (I) and used as antimycotic pharmaceutical combination of drug activity component. The alkaloid not only has obvious antimycotic activity for drug resistant strains to azole antimycotic drugs, but also can be combined and applied with azole drugs and antimycotic drugs as an effective synergist for reversing multidrug resistance of azole antimycotic activity for treating mycotic infection of mammals, which can increase the treating efficiency, reduce the using dosage of azole antimycotic drugs and reduce the adverse reaction. The invention provides a new compound for seeking new antimycotic drugs.

Description

Technical field: [0001] The invention belongs to the field of medicines, and in particular relates to aporphylloid alkaloids and their derivatives, the pharmaceutical composition which is the active ingredient of medicines, the antifungal effect and the application in the development of antifungal medicines. Background technique: [0002] At present, there are more than 80 antifungal drugs used clinically in the world. These drugs have different antifungal ranges and modes of action. According to their chemical structures, they can be roughly divided into six categories, namely polyene antifungal antibiotics, pyrimidines, Acrylanilines, morpholines, thiocarbamates and azole antifungal drugs, among which azole antifungal drugs are a class of fully synthetic antifungal drugs with rapid development. Since the discovery of imidazole’s antifungal effect in the late 1960s, nitrogen azole antifungal drugs have developed rapidly, and dozens of drugs such as clotrimazole, miconazole,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/06C07D491/22A61K31/4741A61P31/10
Inventor 徐贵丽饶高雄王慧敏李智敏张森左国营
Owner 成都军区昆明总医院
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