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Compound of dual functional esterified prodrug of Cefetamet, and oral preparation

The technology of a pharmaceutical compound, ceftazidime, is applied in the field of esterified prodrug compounds and their oral preparations, which can solve the problems of low solubility, bitter taste, and low bioavailability, and achieve improved water solubility, increased sweetness, and expanded applications range effect

Inactive Publication Date: 2005-10-26
朱晓茂
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, it has been found through research that the drug still has the following disadvantages: (1) the currently marketed dosage form is a solid preparation, and due to the low solubility of the drug in water, the bioavailability of these oral preparations is low, such as the absolute bioavailability of the tablet. The utilization rate is only 50%, and the rest is excreted from the body, causing a lot of waste
(2) Because the taste of the drug is very bitter, it is not convenient to be used to make various oral preparations such as dispersible tablets, chewable tablets, granules, etc., especially for children and patients with dysphagia.

Method used

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  • Compound of dual functional esterified prodrug of Cefetamet, and oral preparation
  • Compound of dual functional esterified prodrug of Cefetamet, and oral preparation
  • Compound of dual functional esterified prodrug of Cefetamet, and oral preparation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: (6R, 7R)-3-methyl-7-[(2-(N-tert-butoxycarbonyl-(S)-alanylamino-4-thiazolyl)-(methoxyimino )Acetamido)]-8-oxo-5-thia-1-azabicyclo[4,2,0]-2-ene-2-carboxylic acid trimethylacetoxymethyl ester (a 1 ) preparation

[0027] Add 19.2 g of ceftazidime pivoxil and 15 g of N-tert-butoxycarbonyl-L-albamate into 200 ml of dichloromethane, stir at room temperature for 10 minutes, then add 1-ethyl-3-(3-dimethyl Aminopropyl) carbodiimide hydrochloride 15.2g, 4-dimethylaminopyridine 0.44g, stirred and reacted at a temperature of 18-25°C for 2 hours, added 10% citric acid solution 60ml to wash once, 5% NaHCO 3 Wash once with 60ml solution, once with saturated NaCl solution, take the organic phase and add anhydrous MgSO 4 1 g was dried for 30 minutes, filtered, and concentrated to dryness at 40°C to obtain a 1 , 19.4g, content 97.5%, yield 75.7%. C 29 h 40 N 6 o 10 S 2 The elemental analysis values ​​are C, 49.99; H, 5.79; N, 12.06; S, 9.20. Actual measured values: C...

Embodiment 2

[0028] Example 2: (6R,7R)-3-methyl-7-[(2-(s)-alanylamino-4-thiazolyl)-(methoxyimino)acetamido]-8-oxo -5-Thia-1-azabicyclo[4,2,0]-2-ene-2-carboxylic acid trimethylacetoxymethyl ester hydrochloride (b 1 ) preparation

[0029] In the reaction bottle, put a 1 Dissolve 11g in 55ml of formic acid, control the temperature at 10-15°C, add 11ml of ethanol, dropwise add 1.8ml of concentrated HCl, stir for 10 minutes, add 110ml of isopropanol to precipitate a large amount of solid, cool down to 0-5°C, stir and crystallize for 2 hours, Filter, wash twice with isopropanol, and dry under vacuum at 50°C to obtain a powdery off-white solid b 1 , 8.6g, content 98.0%, yield 86.2%. C 23 h 31 ClN 6 o 8 S 2 The elemental analysis values ​​are C, 44.62; H, 5.05; Cl, ​​5.73; N, 13.57; S, 10.36. Actual measured values: C, 44.4; H, 5.12; Cl, ​​5.83; N, 13.49; S, 10.31.

Embodiment 3

[0030] Example 3: (6R,7R)-3-methyl-7-[(2-(N-tert-butoxycarbonyl-glycylamino-4-thiazolyl)-(methoxyimino)acetamido)] -8-Oxo-5-thia-1-azabicyclo[4,2,0]-2-ene-2-carboxylic acid trimethylacetoxymethyl ester (a 2 ) preparation

[0031] Add 19.2 g of ceftazidime pivoxil and 6.6 g of N-tert-butoxycarbonylglycine into 200 ml of dichloromethane, stir at room temperature for 10 minutes, add 1-ethyl-3-(3-dimethylaminopropyl) carbon Diimine hydrochloride 15.2g, 4-dimethylaminopyridine 0.44g, stirred and reacted at a temperature of 18-25°C for 2 hours, then added 60ml of 10% citric acid solution to wash once, 5% NaHCO 3 Wash once with 60ml solution, once with saturated NaCl solution, take the organic phase and add anhydrous MgSO 4 1 g was dried for 30 minutes, filtered, and concentrated to dryness at 40°C to obtain a 2 , 15.7g, yield 62.6%. C 28 h 38 N 6 o 10 S 2 Elemental analysis values: C, 49.26; H, 5.61; N, 12.31; S, 9.39. The actual measured values ​​are: C, 49.15; H, 5.72; ...

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Abstract

The present invention discloses a cefetamet pivovil double-function esterification precursor medicine compound. Said invention also provides its chemical name, structure general formula and various oral dosage forms. Said compound has higher water solubility and strong and high-effective antibacterial activity.

Description

Technical field: [0001] The invention relates to a class of esterified prodrug compounds with the third-generation cephalosporin antibiotic ceftamet as an active ingredient and oral preparations thereof, in particular to a class of esterified prodrug compounds with dual functions and oral preparations thereof preparation. Background technique: [0002] Antibiotic Cefetamet Pivoxil Hydrochloride C 20 h 25 N 5 o 7 S 2 .HCl) is a third-generation oral cephalosporin antibiotic, and ceftazidime is its active substance in vivo. Ceftamet pivoxil hydrochloride mainly enters the gastrointestinal tract after oral administration and is hydrolyzed by intestinal wall esterase to form active ceftazime to exert antibacterial effect. Cefetamet has broad-spectrum and strong antibacterial activity against aerobic and anaerobic Gram-positive bacteria and negative bacteria, and its function is to kill bacteria. antibacterial activity. At the same time, cefetaxime has a strong antibacter...

Claims

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Application Information

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IPC IPC(8): C07D501/22
Inventor 朱晓茂余安国林国华莫兆明白云
Owner 朱晓茂
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