Positively charged water-soluble prodrugs of aspirin

A technology for aspirin, the active ingredient, in the field of positively charged water-soluble aspirin prodrugs

Inactive Publication Date: 2009-07-15
于崇曦 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, with these methods, it is difficult to make the concentratio

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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Embodiment approach

[0063] Preparation of Acetylsalicyloyldimethylaminoethyl Ethyl Acetate

[0064] 19.9 g (0.1 mol) of o-acetoxybenzoyl chloride was 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 (3 x 30ml), 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; measured 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).

[0065] Preparati...

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Abstract

The novel positively charged prodrugs of acetylsalicylic acid and its analogues in the general formula(1) 'Structure 1' were designed and synthesized. The compounds of the general formula(1) 'Structure 1' indicated above can be prepared from functional derivatives of ASA or its analogues,(for example acid halides or mixed anhydrides), by reaction with suitable alcohols, thiols, or amines. The positively charged amino groups of these pro-drugs not only largely increases the solubility of the drugs, but also bonds to the negative charge on the phosphate head group of membranes and push the pro-drug into the cytosol. The experiment results suggest that the pro-drug, diethylaminoethyl acetylsalicylate.AcOH, diffuses through human skin -400 times faster than acetylsalicylic acid itself and -100 times faster than ethyl acetylsalicylate. In plasma, 80% of these pro-drugs can change back to the drug in a few minutes. The pro-drugs can be used medicinally in treating any aspirin-treatable conditions in humans 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 aspirin, most notably GI disturbances such as dyspepsia, gastroduodenal bleeding, gastric ulcerations, and gastritis. Controlled transdermal administration systems of the prodrug enable the aspirin in the blood to reach constantly optimal therapeutic blood levels to increase effectiveness and reduce the side effects of aspirin.

Description

technical field [0001] 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 [0002] 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-reducing, pain-relieving and anti-inflammatory properties. Because salicylates promote the excretion of uric acid, they are also used in the treatment of gout. Aspirin also inhibits platelet aggregation, which may lead to heart attack and stroke [C.H.Hennekens, e...

Claims

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Application Information

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IPC IPC(8): C07C235/42C07C211/64C07C235/16
CPCC07C327/30C07C235/60C07C219/14A61P1/02A61P1/04A61P3/10A61P7/02A61P9/10A61P13/12A61P19/02A61P21/00A61P25/04A61P27/02A61P29/00A61P35/00
Inventor 于崇曦徐丽娜
Owner 于崇曦
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