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Leonurine derivative as well as preparation method and application thereof

A technology of leonurine and derivatives, which is applied in the field of drug synthesis, can solve problems such as low bioavailability of leonurine, and achieve the effects of improving oral bioavailability, cheap and easy-to-obtain raw materials, and easy control.

Active Publication Date: 2018-11-20
北京合力众盈医药科技有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In view of this, the technical problem solved by the present invention is to provide a kind of leonurine derivative, preparation method and application thereof, to solve the problem of low bioavailability of leonurine

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Through the following chemical reaction equation, compound (II) is prepared:

[0041]

[0042] Add 100ml of tetrahydrofuran and 20ml of water into a 250ml three-necked flask, add 3.5g (0.01mol) of motherurine hydrochloride and 3.4g (0.04mol) of sodium bicarbonate, respectively, and stir at 20°C for ten minutes, then add 0.2g of N, N- For dimethyl-4-aminopyridine, 2.45g (0.02mol) of n-propyl chloroformate was dissolved in 10ml of tetrahydrofuran, and the resulting solution was slowly dripped into the reaction flask at 20°C, and continued stirring for 3 hours to After the reaction was completed, tetrahydrofuran was evaporated under reduced pressure, 70ml of saturated brine and 30ml of ethyl acetate were added for extraction, the aqueous layer was extracted twice with 20ml of ethyl acetate respectively, the organic layers were combined, washed twice with dilute citric acid solution, and the organic layer was separated. layer, added 3g of anhydrous sodium sulfate to dry,...

Embodiment 2

[0044] Through the following chemical reaction equation, compound (Ⅲ) is prepared:

[0045]

[0046] Add 200ml of tetrahydrofuran and 20ml of water into a 250ml three-necked flask, add 3.5g (0.01mol) of motherurine hydrochloride and 3.4g (0.04mol) of sodium bicarbonate, and stir at 25°C for ten minutes, then add 0.2g of N, N- Dimethyl-4-aminopyridine, take 2.74g (0.02mol) of isopropyl chloroformate and dissolve in 10ml of tetrahydrofuran, and slowly drop the resulting solution into the reaction flask at 25°C, and continue stirring for 3 hours to After the reaction was completed, tetrahydrofuran was evaporated under reduced pressure, 70ml of saturated brine and 30ml of ethyl acetate were added for extraction, the aqueous layer was extracted twice with 20ml of ethyl acetate respectively, the organic layers were combined, washed twice with dilute citric acid solution, and the organic layer was separated. layer, added 3g of anhydrous sodium sulfate to dry, filtered, and the fil...

Embodiment 3

[0048] Through the following chemical reaction equation, compound (Ⅳ) is prepared:

[0049]

[0050] Add 400ml of tetrahydrofuran and 30ml of water into a 250ml three-necked flask, add 3.5g (0.01mol) of motherurine hydrochloride and 5.1g (0.06mol) of sodium bicarbonate, and stir at 23°C for ten minutes, then add 0.3g of N, N- Dimethyl-4-aminopyridine, take 4.44g (0.03mol) of n-heptanoyl chloride and dissolve it in 20ml of tetrahydrofuran, and slowly drop the resulting solution into the reaction flask at 23°C, and continue stirring for 3.5 hours until the reaction is completed. After the end, the tetrahydrofuran was evaporated under reduced pressure, 80ml of saturated brine and 40ml of ethyl acetate were added for extraction, the aqueous layer was extracted twice with 30ml of ethyl acetate respectively, the organic layers were combined, washed twice with dilute citric acid solution, and the organic layer was separated , adding 6g of anhydrous sodium sulfate for drying, filte...

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Abstract

The invention discloses a leonurine derivative as well as a preparation method and application thereof. In a compound and pharmaceutically acceptable salt or prodrug thereof as shown in a formula (I),R1, R2 and R3 are the same or different and are independently selected from hydrogen, C1-C10 linear chain or branched alkyl carbonyl or C1-C10 linear chain or branched alkoxyl carbonyl. Relative to the leonurine in the prior art, the leonurine derivative as shown in the formula (I) has the following advantages: the bioavailability of the leonurine derivative in the animal body is greatly improved; furthermore, the leonurine derivative in blood is hydrolyzed into leonurine rapidly, and the condition of low exposed quantity caused by the fact that the leonurine is absorbed insufficiently in theliving body is improved. (The formula is as shown in the description).

Description

technical field [0001] The present invention relates to the technical field of medicine synthesis, more specifically, the present invention relates to a kind of leonurine derivative, preparation method and application thereof. Background technique [0002] Motherwort is a commonly used traditional Chinese medicine. It is the fresh or dried aerial part of Leonurus japonicus Houtt., a plant of the Labiatae family. According to the Chinese Pharmacopoeia, the functions and indications of Motherwort include: promoting blood circulation and regulating menstruation, diuresis and swelling, clearing heat and detoxifying. For irregular menstruation, dysmenorrhea amenorrhea, lochia endlessly, edema oliguria, sore swelling poison. At present, there are many motherwort and compound products of motherwort on the market. [0003] Leonurine is an active ingredient in Motherwort, and predecessors have done a lot of research work on the pharmacological effects of Motherwort. Leonurine has e...

Claims

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Application Information

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IPC IPC(8): C07C279/24C07C279/22C07C277/08A61P15/04A61P7/02A61P9/10A61P13/08A61P39/06
CPCA61P7/02A61P9/10A61P13/08A61P15/04A61P39/06C07C277/08C07C279/22C07C279/24
Inventor 苏为民郑宇
Owner 北京合力众盈医药科技有限责任公司
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