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Positively-charged water-soluble prodrugs of aspirin

A kind of technology of aspirin, drug, applied in the field of positively charged water-soluble aspirin prodrug

Inactive Publication Date: 2014-07-16
TECHFIELDS BIOCHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, with these methods, it is difficult to make the concentration of aspirin in plasma reach the plasma level of effective treatment.

Method used

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  • Positively-charged water-soluble prodrugs of aspirin
  • Positively-charged water-soluble prodrugs of aspirin
  • Positively-charged water-soluble prodrugs of aspirin

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Experimental program
Comparison scheme
Effect test

Embodiment approach

[0060] Preparation of Acetylsalicyloyldimethylaminoethyl Ethyl Acetate

[0061] 19.9 g (0.1 mol) of o-acetoxybenzoyl chloride were dissolved in 100 ml of chloroform. The mixture was cooled to 0°C. 15ml of triethylamine and 8.9g of dimethylaminoethanol were added to the reaction mixture. Stir at room temperature for 3 hours. Stir and add 6 g of acetic acid to the reaction mixture. The solid by-product was filtered off, washed with chloroform (3x30ml), and the organic solvent was evaporated to dryness. After drying, 29 g of the target product (93%) were obtained. Damp product; Solubility: 350mg / ml; Elemental analysis: C 15 h 21 NO 6 ;Molecular weight: 311.33. Theoretical value (%): C: 57.87; H: 6.80; N: 4.50; O: 30.83; found value: C: 57.82; H: 6.85; N: 4.48; 1 H-NMR (400MHz, deuterated chloroform solvent): data: 2.09 (s, 3H) 2.21 (s, 3H), 2.90 (s, 6H); 3.71 (m, 2H), 4.69 (m, 2H), 6.9 ( b, 1H), 7.18 (m, 1H), 7.20 (m, 1H), 7.47 (m, 1H), 7.93 (m, 1H).

[0062] Preparati...

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Abstract

Novel positively-charged prodrugs in a general formula (1) 'structure 1' of acetylsalicylic acid and acetylsalicylic acid analogues are designed and synthesized. The compounds of the general formula (1) 'structure 1' can be prepared by reacting functional derivatives (for example acid halides or mixed anhydrides) of acetylsalicylic acid or acetylsalicylic acid analogues with suitable alcohols, thiols or amines. The positively-charged amino groups of the pro-drugs not only substantially increase the solubility of the drugs, but also bond to negative charges at the phosphate terminal of biological membranes and push prodrug molecules into the cellular fluid. Experiment results suggest that the prodrug diethylaminoethyl acetylsalicylate-acetate has a human skin penetration speed faster than that of acetylsalicylic acid by nearly 400 times, and faster than that of ethyl acetylsalicylate by nearly 100 times. In plasma, 80% of the prodrug can change back to the drug in a few minutes. The prodrugs can be used medicinally in treating any aspirin-treatable diseases of human or animals and be administered not only orally, but also transdermally for any kind of medical treatments and avoid most of the side effects of acetylsalicylic acid and acetylsalicylic acid analogues, most notably side effects such as dyspepsia, gastroduodenal bleeding, gastric ulcerations and gastritis. A controlled transdermal administration systems of the prodrug enables acetylsalicylic acid and acetylsalicylic acid analogues in the blood to reach constantly optimal therapeutic blood levels to increase curative effect and reduce the side effects of acetylsalicylic acid.

Description

[0001] Divisional statement [0002] This application is a divisional application of the Chinese patent application filed on July 9, 2006 with the application number 200680055301.8 and the invention title "Positively charged water-soluble aspirin prodrug". technical field [0003] The present invention relates to positively charged, water-soluble prodrugs of aspirin or its analogues and their use in the treatment of any aspirin-treatable disease in humans or animals. In particular, the present invention aims to overcome the side effects caused by the use of salicylates. These prodrugs can be used orally or topically. technical background [0004] Acetylsalicylic acid (aspirin) was synthesized in 1853 and first used in medicine in 1899. Since then, a variety of salicylic acid derivatives have been synthesized and evaluated for pharmacological efficacy, however only a relatively small number of derivatives have been successfully used for medical use. Aspirin has fever-reduc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C219/14C07C235/60C07C327/30A61K31/621A61K31/616A61P29/00A61P19/02A61P15/00A61P9/00A61P7/02A61P9/10A61P1/00A61P27/12A61P3/10A61P13/12A61P35/00A61P27/02A61P17/10A61P17/00A61P11/06
Inventor 于崇曦徐丽娜
Owner TECHFIELDS BIOCHEM CO LTD
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