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Novel rebamipide prodrug, method for producing same, and usage thereof

一种药学、烷基的技术，应用在新型瑞巴派特前药领域，达到吸收性能改善、体内吸收性能增强的效果

Active Publication Date: 2015-05-27
SAMJIN PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

No other technique has been found to be effective in increasing the bioavailability of rebamipide

Method used

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  • Novel rebamipide prodrug, method for producing same, and usage thereof
  • Novel rebamipide prodrug, method for producing same, and usage thereof
  • Novel rebamipide prodrug, method for producing same, and usage thereof

Examples

Experimental program
Comparison scheme
Effect test

experiment approach A

[0251]

[0252] The compound of chemical formula II was dissolved in DMF (dimethylformamide, 8-10 times the volume of the compound of chemical formula II) at high temperature, and then quenched to 0°C. To this mixture were added DCC (dicyclohexylcarbodiimide, 1-1.5 equivalents) and DMAP (dimethylaminopyridine, 0.1-0.3 equivalents). When the internal temperature became stable, alcohol or amine (1-1.2 equivalents) was slowly added. The resulting mixture was stirred at room temperature for 4 to 24 hours. The product thus formed was obtained by filtration followed by removal of DMF in vacuo. Subsequently, the residue was subjected to column chromatography using dichloromethane:methanol (9:1, v / v) to obtain the compound of formula I as a solid. Recrystallization was performed when necessary.

experiment approach B

[0254]

[0255] The compound of chemical formula II was dissolved in DMF (dimethylformamide, 8-10 times the volume of the compound of chemical formula II) at high temperature, and then quenched to 0°C. Add EDCI (1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride, 1 to 3 equivalents) and HOBT (1-hydroxybenzotriazole, 1 to 3 equivalents). When the internal temperature became stable, alcohol or amine (1-1.5 equivalents) was slowly added. The resulting mixture was stirred at room temperature for 4 to 24 hours. The product thus formed was obtained by filtration followed by removal of DMF in vacuo. Subsequently, the residue was subjected to column chromatography using dichloromethane:methanol (9:1, v / v) to obtain the compound of formula I as a solid. Recrystallization was performed when necessary.

experiment approach C

[0257]

[0258] In the compound of chemical formula II, add DMF (dimethylformamide, 8~10 times of the volume of the compound of chemical formula II), halogen compound (1~1.5 equivalent) and inorganic salt (1~2 equivalent) successively, and make gained The mixture is reacted at 20-80° C. for 1-24 hours. After completion of the reaction, the product was obtained by filtration followed by removal of DMF in vacuo. The residue was subjected to column chromatography using dichloromethane:methanol (9:1, v / v) to afford the compound of formula I as a solid. Recrystallization was performed when necessary.

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PUM

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Abstract

Disclosed are a novel rebamipide prodrug, a method for preparing the same, and use thereof. Also, a pharmaceutical composition comprising the novel rebamipide prodrug as an active ingredient is provided. The rebamipide prodrug is increased 25-fold in absorption rate compared to rebamipide itself, and can be applied to the prophylaxis or therapy of gastric ulcer, acute gastritis, chronic gastritis, xerophthalmia, cancer, osteoarthritis, rheumatoid arthritis, or obesity.

Description

technical field [0001] The present invention relates to novel rebamipide prodrug, its preparation method and use. More specifically, the present invention relates to a novel prodrug of rebamipide which maintains the same efficacy as rebamipide but has improved bioavailability, and a method for preparing the prodrug, which is a simple method. Background technique [0002] Rebamipide (system name 2-(4-chlorobenzoylamino)-3-[2(1H)-quinolon-4-yl]propionic acid) is a drug used for peptic ulcer (including gastric ulcer, Excellent therapeutic agent for acute gastritis and gastric mucosal lesions caused by acute exacerbation of chronic gastritis). The drug exerts a gastroprotective function by stimulating the biosynthesis of PGE2 in the gastric mucosa and by promoting the proliferation of endothelial cells. In particular, the drug is prescribed to patients suffering from gastritis caused by Helicobacter pyroli because it prevents bacteria from adhering to and infiltrating gastric ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/227C07D413/12A61K31/4704A61P1/04
CPCA61K31/4704C07D215/227C07D401/12C07D403/12C07D405/12C07D409/12C07D413/12C07D417/12A61P1/04A61P19/02A61P27/02A61P3/04A61P35/00A61P3/06A61P3/10
Inventor 曹义焕崔承柱李成宇申熙钟权镐晳李在雄周定垀金铉泰宋祐宪尹种培朴起锡朴昊俊南昊泰
Owner SAMJIN PHARMA
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