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
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  • 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,...

Method used

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  • 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...

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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

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Application Information

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IPC IPC(8): C07J63/00A61K31/704A61P1/16A61P31/14A61P1/04
Inventor 靳永增仲荣德靳雪峰
Owner BEIJING MEIBEITA DRUG RES
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