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Andrographolide compound and application of andrographolide compound in medicaments

A technology of ester compounds and Andrographis paniculata, applied in the field of preparation methods, andrographolide derivatives, and medicinal compositions, can solve the problems of antipyretic effect and unsatisfactory solubility in water

Active Publication Date: 2011-11-23
SUNSHINE LAKE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, the antipyretic effect and solubility in water of the above-mentioned known medicines are all unsatisfactory

Method used

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  • Andrographolide compound and application of andrographolide compound in medicaments
  • Andrographolide compound and application of andrographolide compound in medicaments
  • Andrographolide compound and application of andrographolide compound in medicaments

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0223] Example 1 3-Acetyl dehydroandrographolide-19-phosphate monoester disodium salt

[0224]

[0225] Step 1) 3-Hydroxy-19-O-trityl dehydroandrographolide

[0226] Dehydroandrographolide (8g, 24mmol), add dichloromethane 64 (ml), catalytic amount of 4-dimethylaminopyridine (DMAP), stir, add triethylamine 6 (ml), triphenylchloromethane (10.06 g, 36mmol) was heated to reflux for 10h, cooled, added dichloromethane (40ml), water (60ml), separated, the organic layer was washed twice with water, extracted with anhydrous Na 2 SO 4 After drying and concentration, the obtained dark yellow liquid was subjected to silica gel column chromatography (ethyl acetate:petroleum ether=1:3), and the collected product was evaporated to dryness to obtain the target compound as a light yellow solid (7 g, 50%).

[0227] Step 2) 3-Acetyl-19-O-trityl dehydroandrographolide

[0228] 3-Hydroxy-19-O-trityl dehydroandrographolide (3.87g, 11.65mmol), a small amount of DMAP, added dichloromethane (25...

Embodiment 2

[0237] Example 2 3-Hydroxydehydroandrographolide-19-o-phosphate monoester disodium salt

[0238]

[0239] Step 1) 3-Hydroxydehydroandrographolide phosphate monoester

[0240] 3-Acetyl-19-O-di-tert-butyl phosphate (200mg, 0.476mmol) and 3.5% hydrochloric acid (10ml) were dissolved in tetrahydrofuran (10ml), stirred for 6h and extracted with ethyl acetate after the compound was almost completely reacted, and the combined organic After the layers were dried over anhydrous sodium sulfate, and then evaporated to dryness, the target compound was obtained as a pale yellow solid (85 mg, 43%).

[0241] Step 2) 3-Hydroxydehydroandrographolide-19-O-phosphate monoester disodium salt

[0242] Dissolve 3-hydroxydehydroandrographolide phosphate monoester (85 mg, 0.20 mmol) in dichloromethane, add 0.7 (ml) of 1M sodium bicarbonate solution dropwise thereto, stir for 3 h, and evaporate the solvent to obtain a brown solid, which is washed with ethyl acetate The ester was washed several tim...

Embodiment 3

[0245] Example 3 19-O-acetyl dehydroandrographolide-3-phosphate monoester disodium salt

[0246]

[0247] Step 1) 3-Hydroxy-19-O-acetyldehydroandrographolide

[0248] Dehydrated andrographolide (10g, 30.12mmol), added dichloromethane (80ml), catalytic amount of DMAP, triethylamine (6ml, 43.3mmol), acetic anhydride (3.65g, 35mmol), stirred and heated to reflux for 20h, cooled, Dichloromethane (20ml) and water 60 (ml) were added, the layers were separated, the organic layer was washed twice with water, the organic layer was evaporated to dryness, and the resulting liquid was subjected to silica gel column chromatography (ethyl acetate:petroleum ether=1:3), The collected product was evaporated to dryness to obtain the title compound as a white solid (2.2 g, 19.6%).

[0249] Step 2) 19-O-Acetyl Dehydroandrographolide Phosphate Monoester Di-tert-Butyl Ester

[0250] 3-Hydroxy-19-O-acetyl dehydroandrographolide (374mg, 1mmol), diethylaminodi-tert-butoxyphosphine (0.63ml, 1mmol)...

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PUM

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Abstract

The invention relates to an andrographolide derivative the structure of which is shown in a formula (I) or (II) and a stereoisomer, a stereomer, a tautomer, a solvate, a polymorph, a metabolin, ester, a pharmaceutically acceptable salt or a prodrug of the derivative. The andrographolide compound provided by the invention has the advantages of good solubility, high purity and good antipyretic property; and the andrographolide compound is especially suitable to be used as an effective component for preparing antipyretic, anti-inflammatory and antimicrobial medicaments.

Description

technical field [0001] The invention relates to the field of chemical pharmacy, in particular to andrographolide derivatives, preparation methods, medicinal compositions and applications thereof. Background technique [0002] Andrographis Paniculata (Burm.f.) Nees, also known as Yijianxi, Snake Sword, Bitter Grass, and Lavender, can clear away heat and detoxify, cool blood, and reduce swelling. , coughing and coughing, diarrhea and dysentery, hot stranguria and astringent pain, carbuncle sores, poisonous snake bites, etc. The molecular structure of its active ingredients is as follows: [0003] [0004] Andrographis paniculata is a widely used herbal drug for clearing away heat and detoxifying clinically. It has been included in the Chinese Pharmacopoeia (2000) with 220 pages. More studies, mostly think that its main active ingredient is a diterpene lactone compound, such as andrographolide (Andrographolide), dehydroandrographolide (Dehydroandrographolide) etc. ; Pharma...

Claims

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Application Information

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IPC IPC(8): C07F9/655C07F9/6574C07D307/60C07D307/58A61K31/665A61K31/683A61K31/365A61P19/02A61P1/00A61P29/00A61P31/12A61P31/04
Inventor 张健存张英俊关启明汪东峨刘伟平
Owner SUNSHINE LAKE PHARM CO LTD
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