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Positively charged water-soluble prodrugs of oxicams and related compounds with very high skin penetration rate

A technology of compounds and active ingredients, applied in the field of prodrugs of positively charged water-soluble xicam and related compounds with fast skin penetration speed, can solve the problems of difficult drug, delivery, slow skin penetration and the like

Inactive Publication Date: 2009-09-02
于崇曦 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the slow transdermal rate, it is difficult to deliver these drugs into the host body and achieve therapeutically effective plasma concentrations through formulations

Method used

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  • Positively charged water-soluble prodrugs of oxicams and related compounds with very high skin penetration rate
  • Positively charged water-soluble prodrugs of oxicams and related compounds with very high skin penetration rate
  • Positively charged water-soluble prodrugs of oxicams and related compounds with very high skin penetration rate

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Experimental program
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Embodiment approach

[0055] N-(2-thiazolyl)-4-N,N-dimethylaminobutyryloxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide Preparation of substance hydrochloride

[0056]32.5g (0.1mol) N-(2-thiazolyl)-4-hydroxyl-2-methyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide and 16g (0.1 mol) diethylaminobutyric acid was dissolved in 300 ml of dichloromethane. The reaction mixture was cooled to 0°C with an ice bath. To the reaction mixture was added 20.6 g (0.1 mol) of N,N'-dicyclohexylcarbodiimide. The mixture was stirred at 0°C for 1 hour and at room temperature for 2 hours. The solids were removed by filtration. The dichloromethane solution was washed twice with 5% sodium bicarbonate solution, 100 ml each time, and washed 3 times with water, 100 ml each time. The organic layer was dried over anhydrous sodium sulfate. Sodium sulfate was removed by filtration. 4g of hydrochloric acid gas was introduced into the solution. The solid product was collected by filtration. After drying, 37 g of...

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Abstract

The novel positively charged pro-drugs of oxicams and related compounds in the general formula (1) 'Structure 1' were designed and synthesized. 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 pushes the pro-drug into the cytosol. The results suggest that the pro-drugs diffuses through human skin approximately 100 times faster than do oxicams and related compounds. It takes 1-2 hours for oxicams and related compounds to reach the peak plasma level when they are taken orally, but these prodrugs only took about approximately 50 minutes to reach the peak plasma level when they are taken transdermally. In plasma, more than 90% of these pro-drugs can change back to the parent drugs in a few minutes. The prodrugs can be used medicinally in treating any oxicams-treatable conditions in humans or animals. Second, the prodrugs can be administered not only orally, but also transdermally for any kind of medical treatments and avoid most of the side effects of oxicams. Controlled transdermal administration systems of the prodrugs enable oxicams and related compounds to reach constantly optimal therapeutic blood levels to increase effectiveness and reduce the side effects of oxicams and related compounds. Another great benefit of the transdermal administration of these pro-drugs is that administering medication, especially to children, will be much easier.

Description

technical field [0001] The present invention relates to positively charged, water-soluble prodrugs of oxicam and related compounds thereof and their use in the treatment of any oxicam-treatable condition in humans or animals. Specifically, the present invention aims to overcome the side effects caused by the use of Oxycam and its related compounds. These prodrugs can be administered orally or transdermally. Background technique [0002] Piroxicam, sudoxicam, lornoxicam, tenoxicam, ampiraxicam, lornoxicam (lomoxicam), isoxicam, sinoxicam, meloxicam and their related compounds belong to Member of the enolic acid class of 4-hydroxy-1,2-benzothiazine-carboxamides with anti-inflammatory and analgesic properties. The first member of this class of compounds, piroxicam, was marketed in the United States in 1982 under the trade name Feldene (Pfizer). Oxicam is a very important class of analgesic and antipyretic drugs. They can be used to relieve symptoms of rheumatoid arthritis, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/04C07D417/12C07D279/16
CPCC07D513/04C07D279/02C07D417/12A61P1/02A61P1/04A61P1/08A61P1/18A61P11/06A61P15/00A61P15/14A61P17/00A61P17/06A61P17/10A61P19/02A61P19/10A61P21/00A61P25/00A61P25/04A61P25/06A61P27/02A61P27/06A61P27/16A61P29/00A61P35/00A61P43/00
Inventor 于崇曦徐丽娜
Owner 于崇曦
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