Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Nitrate derivatives of glycyrrhetic acid and glycyrrhetinic acid and pharmaceutical use thereof

A kind of technology of glycyrrhetic acid, nitrate, applied in the application field of aspect

Inactive Publication Date: 2006-09-06
BEIJING MEIBEITA DRUG RES
View PDF0 Cites 14 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] However, glycyrrhizic acid or glycyrrhetinic acid and its derivatives still have some adverse reactions in clinical application, mainly including anorexia, nausea, vomiting, abdominal distension, skin itching, urticaria, dry mouth, edema, dizziness, chest tightness, palpitations, Increased blood pressure, also has some steroid-like side effects (Edited by Chen Xinqian et al., Newly Edited Pharmacology, 15th Edition, People's Health Publishing House, 2004, pages 421, 440, 442 and 472)

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Nitrate derivatives of glycyrrhetic acid and glycyrrhetinic acid and pharmaceutical use thereof
  • Nitrate derivatives of glycyrrhetic acid and glycyrrhetinic acid and pharmaceutical use thereof
  • Nitrate derivatives of glycyrrhetic acid and glycyrrhetinic acid and pharmaceutical use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1 18α glycyrrhizinyl-tris(2-nitrooxy-ethyl)-ester (II 1 ) Preparation 1a, 18α Glycyrrhizinyl-tris(2-bromo-ethyl)-ester

[0046] Suspend 1.78 g (2 mmol) of 18α trisodium glycyrrhizinate in 10 ml of DMF, add dropwise 1.5 g (8 mmol) of 1,2-dibromoethane, react at room temperature for 22 hours, filter, remove sodium bromide, and depressurize the filtrate Evaporate to dryness, separate the residue by silica gel column chromatography, elute with methanol / dichloromethane (1:1), collect the desired components, and evaporate to dryness under reduced pressure to obtain 1.86 g of 18α-glycyrrhizinyl-tri(2-bromo -ethyl)-ester. 1b, 18α glycyrrhizinyl-tris(2-nitrooxy-ethyl)-ester (II 1 ) preparation

[0047] Dissolve 1.86 g (1.63 mmol) of 18α glycyrrhizinyl-tris(2-bromo-ethyl)-ester in 10 ml of acetonitrile, 1.1 g (6.52 mmol) of AgNO 3 Dissolve in 2 ml of acetonitrile. AgNO 3 The acetonitrile solution was added dropwise to the solution of glycyrrhizinyl-tris(2-bromo-ethy...

Embodiment 2

[0048] Example 2 18α glycyrrhizinyl-tris(4-nitrooxy-butyl)-ester (II 2 ) Preparation of 2a, 18α Glycyrrhizinyl-tris(4-bromo-butyl)-ester

[0049] Suspend 1.78 g (2 mmol) of 18α trisodium glycyrrhizinate in 10 ml of DMF, add dropwise 1.73 g (8 mmol) of 1,4-dibromobutane, react at room temperature for 22 hours, filter, remove sodium bromide, and depressurize the filtrate Evaporate to dryness, separate the residue by silica gel column chromatography, elute with methanol / dichloromethane (1:1), collect the desired components, and evaporate to dryness under reduced pressure to obtain 1.37 g of 18α-glycyrrhizinyl-tri(4-bromo -butyl)-ester. 2b, 18α glycyrrhizinyl-tris(4-nitrooxy-butyl)-ester (II 2 ) preparation

[0050] Dissolve 1.37 g (1.21 mmol) of 18α glycyrrhizinyl-tris(4-bromo-butyl)-ester in 10 ml of acetonitrile, 0.82 g (4.84 mmol) of AgNO 3 Dissolve in 2 ml of acetonitrile. AgNO 3 The acetonitrile solution was added dropwise to the solution of glycyrrhizinyl-tri(4-bromo-...

Embodiment 3

[0051] Example 3 18α Glycyrrhizinyl-tris(3-nitrooxy-3-methyl-propyl)-ester (II 3 ) preparation

[0052] 3a, 18α Glycyrrhizinyl-tris(3-bromo-3-methyl-propyl)-ester

[0053] Suspend 1.78 g (2 mmol) of 18α trisodium glycyrrhizinate in 10 ml of DMF, add dropwise 1.73 g (8 mmol) of 1,3-dibromobutane, react at room temperature for 22 hours, filter, remove sodium bromide, and depressurize the filtrate Evaporate to dryness, separate the residue by silica gel column chromatography, elute with methanol / dichloromethane (1:1), collect the desired components, and evaporate to dryness under reduced pressure to obtain 1.20 g of 18α-glycyrrhizinyl-tri(3-bromo -3-Methyl-propyl)-ester.

[0054] 3b, 18α glycyrrhizinyl-tris(3-nitrooxy-3-methyl-propyl)-ester (II 3 ) preparation

[0055] Dissolve 1.20 g (1.06 mmol) of 18α glycyrrhizinyl-tris(3-bromo-3-methyl-propyl)-ester in 10 ml of acetonitrile, 0.72 g (4.24 mmol) of AgNO 3 Dissolve in 2 ml of acetonitrile. AgNO 3 The acetonitrile solution...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

Disclosed are nitrate derivant of glycyrrhizic acid or glycor represented by formula Ia and Ib and its nontoxic salt which can be accepted in the sphere of pharmacy, their precoss for preparing, and components and usage of the drugs which contain these compounds.Thereinto, R1, R2 and R3 stand for hydroxyl or -X-L-oxo-oxonitryl (X stands for oxygen,imino; L stands for alkyl with 2-6 of canbon atoms, substituted alkyl or cycloalkyl, hydroxyl amino acid residue or N,Ní»-disubstituted piperazine); R3 stands for hydrogen, oxonitryl or carbonyl -Lí»oxo-oxonitryl (Lí»stands for alkyl with 1-6 of canbon atoms, substituted alkyl or cycloalkyl, aralkyl, N,Ní»-disubstituted piperazine); in formula Ib, R1, R2 and R3 may be the same or different, but in which at least one of them contains -X-L-oxo-oxonitryl; in formula Ib, at least one of R3 or R4 must contain oxonitryl. In formula Ia and Ib, hydrogen of 18-carbon can be alpha-isomer or beta-isomer.

Description

technical field [0001] The present invention relates to glycyrrhizic acid and glycyrrhetinic acid nitrate derivatives and non-toxic pharmaceutically acceptable salts thereof, pharmaceutical compositions containing these compounds as active ingredients and their use in the preparation of hepatitis treatment medicines and ulcer treatment medicines, etc. Application; The present invention also relates to the preparation method of glycyrrhizic acid and glycyrrhetinic acid nitrate derivatives and their non-toxic pharmaceutically acceptable salts. Background technique [0002] The present invention relates to glycyrrhizic acid and nitrate derivatives of glycyrrhetinic acid and their non-toxic pharmaceutically acceptable salts, their preparation methods, and pharmaceutical compositions containing these compounds, and by administering an effective therapeutic amount of glycyrrhetinic acid Or nitrate derivatives of glycyrrhetinic acid and non-toxic pharmaceutically acceptable salts t...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07J63/00A61K31/704A61P1/16A61P31/14A61P1/04
Inventor 靳永增仲荣德靳雪峰
Owner BEIJING MEIBEITA DRUG RES
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com