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Application of clinafloxacin amino derivatives and medicinal salts thereof in preparing antitubercular medicaments

A derivative, star amino technology, applied in medical preparations containing active ingredients, antibacterial drugs, pharmaceutical formulations, etc., can solve unclear problems

Active Publication Date: 2013-11-27
SOUTHWEST UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, whether these derivatives have new pharmacological activities in addition to antibacterial activity is still unclear and needs further research.

Method used

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  • Application of clinafloxacin amino derivatives and medicinal salts thereof in preparing antitubercular medicaments
  • Application of clinafloxacin amino derivatives and medicinal salts thereof in preparing antitubercular medicaments
  • Application of clinafloxacin amino derivatives and medicinal salts thereof in preparing antitubercular medicaments

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Embodiment 1, the synthesis of compound TM1

[0019]

[0020] Add clinfloxacin (CF), K 2 CO 3 and an appropriate amount of dichloromethane (DCM), drop the DCM solution of chloroacetyl chloride under ice bath, CF, K 2 CO 3 The molar ratio of feeding to chloroacetyl chloride is 10:25:15-25. After dropping, stir the reaction under ice bath, and monitor the progress of the reaction by TLC (thin layer chromatography). After the reaction was completed, a yellow-green turbid liquid was obtained, which was filtered with suction, and the filter cake was washed with DCM. The washing liquid and the filtrate were combined, and rotary evaporated to dryness to obtain intermediate IM1.

[0021] Add the amine component, K 2 CO 3 And catalytic amount of KI and appropriate amount of solvent, after stirring at room temperature for 30 minutes, add intermediate IM1, IM1, K 2 CO 3 The molar ratio of the feed to the amine component is 1:3:2, the temperature is controlled at 30-45°C,...

Embodiment 2

[0035] The synthesis of embodiment 2, compound TM2

[0036]

[0037] Add CF and an appropriate amount of chloroform to the reaction flask, and after stirring evenly, slowly add a chloroform solution of bis(trichloromethyl)carbonate (BTC) dropwise. Triethylamine (TEA), the feeding molar ratio of CF, BTC and TEA is 17:6:10, dropwise is finished, reacts at room temperature, TLC monitors reaction process. After the reaction was completed, filter with suction, wash the filter cake with DCM, combine the washing liquid and the filtrate, add water, adjust the pH to 4-5 with 2N HCl, then extract twice with DCM, collect the organic phase, wash twice with saturated saline, no Dry over sodium sulfate, filter, concentrate the filtrate by rotary evaporation, and purify by flash column chromatography to obtain intermediate IM2.

[0038] Add chloroform, amine component, and K to the reaction vial 2 CO 3 , after stirring at room temperature for 0.5 hours, add intermediate IM2, amine comp...

Embodiment 3

[0048] The synthesis of embodiment 3, compound TM3

[0049]

[0050] Add 12 mmol of amino acid Boc-AA-OH whose amino group is protected by tert-butoxycarbonyl (Boc) and 20 mL of DCM to the reaction flask, stir for 1 min, add 1-hydroxybenzotriazole (HOBt) 12 mmol and bicyclic Hexylcarbodiimide (DCC) 15mmol, stirred for 1min, then added dropwise TEA 1mL, stirred in ice bath for about 30min, until all the raw materials were activated esters, filtered with suction, washed the filter cake with DCM, combined the lotion and filtrate, added Clinfloxacin 10mmol was stirred at room temperature for reaction, and the reaction progress was monitored by TLC. After the reaction is completed, filter with suction, wash the filter cake with DCM, combine the washing liquid and the filtrate, and use 10% (w / w) citric acid solution, 0.5mol / L NaHCO 3 solution, saturated NaCl solution, the organic phase was collected, anhydrous NaCl 2 SO 4 Drying, rotary evaporation, and purification by column ...

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Abstract

The invention discloses an application of clinafloxacin amino derivatives and medicinal salts thereof in preparing antitubercular medicaments. In the structural general formula of the clinafloxacin amino derivatives, R is -(CH2)nNR<1>R<2>, -CH(CH2CH2XCH3)NH2, 2-pyrrolidyl or -OR3; n is 0 or 1; R1 and R2 are separately hydrogen, methyl, 2-hydroxyethyl, (R)-1-ethyl-2-hydroxyethyl, 2-aminoethyl, 3-(dimethylamino)propyl, hydroxyl, amino, methylamino, methoxyl or thiourea group; X is S or SO2; R3 is methyl or isobutyl; the compounds have certain inhibitory effect on standard sensitive strains, clinically isolated sensitive strains and clinically isolated drug-resistant strains of mycobacterium tuberculosis, the antitubercular activity of a part of compounds is stronger than that of ofloxacin and clinafloxacin and weaker than that of moxifloxacin, thus providing a new research direction for the antitubercular medicaments, and being beneficial to clinical treatment of tuberculosis.

Description

technical field [0001] The invention belongs to the field of chemistry and relates to the new application of compounds in the field of pharmacy. Background technique [0002] Tuberculosis caused by mycobacteria is a highly contagious chronic disease, and its infection rate in the population has remained high since ancient times. my country is one of the 22 countries with a high burden of tuberculosis in the world, and the number of patients ranks second in the world after India. There are many reasons for the rise of tuberculosis in some areas, such as the sudden increase of floating population, the spread of drug-resistant tuberculosis, the dual infection of tuberculosis and HIV, and more importantly, the general lack of attention to tuberculosis health education, Knowledge about tuberculosis prevention and treatment is not popularized. Currently, the first-line treatment drugs for common tuberculosis, such as rifampicin (RFP), isoniazid (INH), pyrazinamide (PZA), ethambu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/4709A61P31/06
Inventor 杨大成任正红雷皇书范莉杨艳韩海燕邹艳冶何志琴赵雪晶
Owner SOUTHWEST UNIVERSITY
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