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Catalpol derivative as well as preparation method and application thereof

A derivative, the technology of catalpol, which is applied in the field of catalpol derivatives or their pharmaceutically acceptable salts and their preparation, can solve the problems of limited clinical application and unstable chemical properties

Active Publication Date: 2016-08-03
ANHUI HEALSTAR PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The chemical properties of catalpol are extremely unstable, and acidity, alkalinity and heat can cause decomposition and transformation, and the clinical application is greatly limited

Method used

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  • Catalpol derivative as well as preparation method and application thereof
  • Catalpol derivative as well as preparation method and application thereof
  • Catalpol derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: Compound I 1 Preparation

[0031] A 100ml dry three-necked flask is equipped with a stirrer and a thermometer. Catalpol (2.3g, 6.35mmol) and 46ml of dry anhydrous acetonitrile are added to it. With stirring, slowly add a methanol solution of dimethylamine (7ml, 8.56mmol), The temperature is raised to 45~50℃ and reacted for 6 hours. TLC identifies the end point of the reaction [thin layer development conditions (petroleum ether-ethyl acetate: methanol = 2:1:0.1)]. The reaction is complete. Concentrate to dryness under reduced pressure at <40°C, add acetone-methyl isopropyl ether to recrystallize the residue, filter, wash the solid with an appropriate amount of ether, and dry under vacuum at 35°C to 40°C for 6 hours to obtain 1.97 g of light yellow crystalline powdery solid The yield is 75.2%, and the HPLC content is 98.1%. HPLC method: use octadecylsilane bonded silica gel as filler, water-acetonitrile (99:1) as mobile phase, detection wavelength at 210nm, flow r...

Embodiment 2

[0038] Example 2: Compound I 1 Preparation of fumarate

[0039] 10ml three-necked flask, add I 1 Compound (0.8g, 1.96mmol) and 5ml of ethanol, add fumaric acid (0.29g, 2.5mmol) at room temperature, ultrasound for 10min, cool to -5℃~0℃ and let stand overnight, filter, and wash the solid with cold ethanol It was dried under vacuum at 35°C to 40°C to obtain 0.79 g of a pale yellow powdery solid with an HPLC content of 99.3%.

Embodiment 3

[0040] Example 3: Compound I 2 Preparation of fumarate

[0041] 1) 100ml dry three-necked flask, equipped with a stirrer and thermometer, add catalpol (2.3g, 6.35mmol) to it

[0042] And dry anhydrous acetonitrile 46ml and ammonium chloride (0.17g, 3.175mmol), under stirring, add sodium azide (0.46g, 7.1mmol), stir at room temperature for 24h, TLC identifies the end of the reaction [thin layer development conditions ( Petroleum ether-ethyl acetate: methanol=2:1:0.1)], after the reaction is complete, filter, filtrate Concentrate to dryness under reduced pressure at <40°C, add methyl ethyl ketone-methyl isopropyl ether to recrystallize the residue, filter, wash the solid with an appropriate amount of ether, and vacuum dry at 35°C to 40°C for 6 hours to obtain a pale yellow crystalline powdered solid 2.22 g, yield 86.3%, HPLC content 95.6%, directly used in the next step.

[0043] 2) The product from the previous step is added to 50ml of absolute ethanol, ferric chloride (1.48g, 5.48mm...

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PUM

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Abstract

The invention belongs to the technical field of medicinal chemistry and medicine, and discloses a catalpol derivative or pharmaceutically acceptable salts thereof, as well as a preparation method and application of the catalpol derivative or the pharmaceutically acceptable salts thereof. The structural formula of the catalpol derivative or the pharmaceutically acceptable salts thereof is shown as the formula (I), wherein R1 is a hydrogen atom or a C1-C4 branched chain or branched paraffin. The compounds or the pharmaceutical salts thereof have wide pharmacologic actions.

Description

Technical field [0001] The present invention relates to the fields of medicinal chemistry and medical technology, and in particular to a catalpol derivative represented by formula (I) or a pharmaceutically acceptable salt thereof, a preparation method thereof, and a pharmaceutical application. Background technique [0002] Diabetes is a chronic and progressive disease that has shown rapid growth in recent years and is becoming younger. In 2010, there were more than 50 million diabetic patients in my country, with an average age of 45 years. Diabetes is characterized by chronic hyperglycemia, accompanied by disorders of sugar, fat and protein metabolism caused by defects in insulin secretion and or action. Type II diabetes accounts for more than 90% of all diabetic patients. [0003] At present, the clinical drugs used to treat diabetes are mainly chemical drugs, such as metformin, angiotensin-converting enzyme inhibitors, insulin sensitizers, etc., but long-term use of them has re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/04C07H1/00A61K31/7048A61P7/10A61P9/10A61P25/00A61P3/10
CPCC07H1/00C07H17/04
Inventor 徐奎王玮陶俊钰
Owner ANHUI HEALSTAR PHARM CO LTD
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