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Positively charged, water-soluble prodrugs of ketoprofen and related compounds with fast skin penetration rates

A compound and composition technology, applied in the field of water-soluble prodrugs, can solve problems such as slow skin penetration

Active Publication Date: 2019-08-30
TECHFIELDS BIOCHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the slow skin penetration of these drugs, it is difficult to achieve therapeutically effective plasma concentrations by means of formulations

Method used

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  • Positively charged, water-soluble prodrugs of ketoprofen and related compounds with fast skin penetration rates
  • Positively charged, water-soluble prodrugs of ketoprofen and related compounds with fast skin penetration rates
  • Positively charged, water-soluble prodrugs of ketoprofen and related compounds with fast skin penetration rates

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Experimental program
Comparison scheme
Effect test

Embodiment approach

[0063] 1. Synthesis of 2-(3-phenoxyphenyl) dimethylaminoethyl propionate acetate

[0064] 26.1 g (0.1 mol) of 2-(3-phenoxyphenyl)propionyl chloride was dissolved in 100 ml of chloroform. The mixture was cooled to 0°C. 15 ml of triethylamine and 8.9 g (0.1 mol) of dimethylaminoethanol were added to the reaction mixture with stirring. The mixture was stirred at room temperature for 3 hours. The solvent was evaporated to dryness. The residue was dissolved in 300 ml methanol. 200 ml of 5% aqueous sodium bicarbonate solution was added to the reaction mixture. The mixture was stirred for 3 hours. The mixture was evaporated to dryness. 300 ml of methanol were added to the residue with stirring. The solid was removed by filtration and washed with methanol. The solution was evaporated to dryness, and the residue was dissolved in 200 ml of chloroform. 6 g of acetic acid was added to the reaction mixture with stirring. The solids were removed by filtration. An additional 6 g o...

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Abstract

The invention discloses a pharmaceutical composition, which comprises a compound as shown in a structural formula 1, and an application of the pharmaceutical composition in preparation of medicines in a treatable condition of ketoprofen or fenoprofen for treating people or animals. The invention furtherdiscloses a transdermal therapy application systemcontaining the pharmaceutical composition.

Description

technical field [0001] The present invention relates to positively charged water-soluble precursors of 2-(3-benzoylphenyl)propionic acid (ketoprofen) and 2-(3-phenoxyphenyl)propionic acid (phenoprofen). Medicine and its use in the treatment of any ketoprofen and fenoprofen treatable condition in man or animal. Specifically, the present invention is to overcome the side effects caused by using ketoprofen and fenoprofen. These prodrugs can be administered orally or transdermally. [0002] technical background [0003] Ketoprofen and fenoprofen are propionate NSAIDs. Ketoprofen was synthesized in 1986 and has since been widely used to relieve the signs and symptoms of rheumatoid arthritis and osteoarthritis, as well as to treat dysmenorrhea. Ketoprofen can be used alone or as an adjunct in the treatment of acute biliary colic, renal colic, pain from oral surgery, severe postpartum pain, and fever (PDRGenerics, 1996, second edition, Medical Economics, Montvale, New Jersey, pg ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/192A61P11/06A61P29/00A61P35/00A61P1/08A61P3/10A61P25/00A61P19/02A61P19/10A61P27/06A61P17/00A61P17/10A61P17/02A61P25/06
Inventor 于崇曦徐丽娜
Owner TECHFIELDS BIOCHEM CO LTD
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