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Water-soluble ibuprofen prodrug with high skin penetration rate and positive charge

A technology for skin diseases and drugs, applied in the field of water-soluble prodrugs

Inactive Publication Date: 2014-07-30
天津昕晨泰飞尔医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it is difficult to achieve therapeutically effective plasma concentrations of ibuprofen by formulation

Method used

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  • Water-soluble ibuprofen prodrug with high skin penetration rate and positive charge
  • Water-soluble ibuprofen prodrug with high skin penetration rate and positive charge
  • Water-soluble ibuprofen prodrug with high skin penetration rate and positive charge

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0058] Synthesis of dimethylaminoethyl 2-(p-isobutylphenyl)propionate acetate

[0059] 22.5g (0.1mol) of 2-(p-isobutylphenyl)propionyl chloride was dissolved in 100ml of chloroform. The mixture was cooled to 0 °C. 15 ml of triethylamine and 8.9 g of dimethylaminoethanol were added. The mixture was stirred at room temperature for 3 hours. 6 g of acetic acid was added to the reaction mixture with stirring. The solid by-product was removed by filtration and washed three times with 30 mL of chloroform. The organic phase was evaporated. After drying, 31 g of the hygroscopic target product was obtained with a yield of 92%. Solubility in water: 400mg / ml; Elemental analysis: C 19 h 31 NO 4 ;Molecular weight: 337.45. Theoretical %C: 67.63; H: 9.26; N: 4.15; O: 18.96; found %C: 67.60; H: 7.28; N: 4.14; O: 18.98. 1 H-NMR (400MHz, deuterated chloroform solvent): δ: 1.01(d, 6H), 1.52(d, 3H), 2.21(s, 3H), 2.22(m, 1H); 2.51(d, 2H), 2.90 (s, 6H), 3.52 (m, 2H), 3.78 (m, 1H), 4.52 (t...

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Abstract

The invention relates to a water-soluble ibuprofen prodrug with high skin penetration rate and positive charges. The invention discloses the application of a compound shown in a structural formula 1 to preparation of a medicament suitable for transdermal delivery and for treating the conditions that can be treated by ibuprofen, and the application of the compound shown in the structural formula 1 to preparation of an aerosol medicament for treating asthma. The invention also discloses the application of a pharmaceutical composition for transdermal delivery and containing the compound shown in the structural formula 1, the application thereof to preparation of a medicament suitable for transdermal delivery and for treating the conditions that can be treated by ibuprofen, and the application of the pharmaceutical composition to preparation of an aerosol medicament for treating asthma. The invention also discloses a transdermal therapeutic system, which comprises the compound shown in the structural formula 1 or its composition, and a usage method of the transdermal therapeutic system.

Description

[0001] Divisional statement [0002] This application is a divisional application of the Chinese patent application submitted on July 18, 2006 with the application number 200680055379.X and the invention name "Positively charged water-soluble ibuprofen prodrug". technical field [0003] The present invention relates to positively charged water-soluble prodrugs of 2-(p-isobutylphenyl)propionic acid (ibuprofen) and their medical use in the treatment of any ibuprofen-treatable condition in humans or animals . Specifically, the present invention is to overcome the side effects brought by the use of ibuprofen. These prodrugs can be administered orally or transdermally. technical background [0004] Ibuprofen is a propionate NSAID. Ibuprofen was synthesized for the first time in 1964 (J.S.Nicholson and S.S.Adams, Br.Patent No.971,700) and was first used as a medicine in Europe. Ibuprofen was more effective than aspirin in anti-inflammatory and inhibition of prostaglandin biosy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K9/70A61K31/165A61K31/221A61K31/255A61K9/08A61K9/107A61K9/10A61K9/06A61P29/00A61P35/00A61P15/00A61P7/04A61P1/08A61P3/10A61P25/00A61P19/02A61P19/08A61P27/02A61P27/06A61P27/16A61P17/00A61P17/08A61P11/06A61P25/04A61P25/06
Inventor 于崇曦徐丽娜
Owner 天津昕晨泰飞尔医药科技有限公司
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