Gatifloxacin derivative and its preparation method and use

A compound and selected technology, applied in the direction of drug combination, pharmaceutical formula, medical preparations containing active ingredients, etc., can solve problems such as abnormal blood sugar, achieve enhanced antibacterial activity, reduced toxic and side effects, and good antibacterial activity in vitro

Active Publication Date: 2021-10-22
SOUTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it was found clinically that gatifloxacin can cause severe abnormal blood sugar, and it was withdrawn from the market in the United States in 2006 as an antibacterial drug.

Method used

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  • Gatifloxacin derivative and its preparation method and use
  • Gatifloxacin derivative and its preparation method and use
  • Gatifloxacin derivative and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0079] Preparation Example 1: Preparation of IM1

[0080] Add GAT 5mmol, DCM 15mL, NaHCO 3 7.5 mmol, after stirring evenly, slowly add 2.5 mmol of solid phosgene in 5 mL of dichloromethane (DCM) dropwise under ice bath. After the dropwise addition, move to room temperature to stir the reaction, and monitor the reaction progress by TLC. After the reaction was completed, 10 mL of ice-cold saturated NaCl solution was added, and 2N HCl solution was added to adjust the pH value to 4-5, and the liquids were separated. Saturated NaCl solution 10mL washed, separated, organic phase anhydrous NaCl 2 SO 4 After drying, the solvent was removed by rotary evaporation to obtain the pure product IM1.

preparation example 2

[0081] Preparation Example 2: Preparation of IM2

[0082] Into a 100mL round bottom flask, add raw materials GAT 1mmol, NaHCO 3 2.5mmol, DCM 5mL, add dropwise a mixed solution of chloroacetyl chloride 2mmol and DCM 2mL under ice-cooling. After dropping, the reaction was continuously stirred under ice bath, and the reaction progress was monitored by TLC. After the reaction, add a little ice-cold saturated NaCl solution to dissolve the solid, adjust the pH to 4-5 with ice-cold 2N HCl solution, stir evenly, transfer to a separatory funnel for liquid separation, extract twice with DCM, combine the organic phases, and wash with saturated NaCl solution. Water Na 2 SO 4 Dry and remove the solvent by rotary evaporation. The pure product was obtained by recrystallization or column chromatography, dried and weighed to obtain IM2. Preparation Example 3: Preparation of IM3

preparation example 3

[0083] Into a 100mL round bottom flask, add raw materials GAT 1mmol, NaHCO 3 2.5mmol, DCM 5mL, add dropwise a mixed solution of chloropropionyl chloride 2mmol and DCM 2mL under ice-cooling. After dropping, the reaction was continuously stirred under ice bath, and the reaction progress was monitored by TLC. After the reaction, add a little ice-cold saturated NaCl solution to dissolve the solid, adjust the pH to 4-5 with ice-cold 2N HCl solution, stir evenly, transfer to a separatory funnel for liquid separation, extract twice with DCM, combine the organic phases, and wash with saturated NaCl solution. Water Na 2 SO 4 Dry and remove the solvent by rotary evaporation. The pure product was obtained by recrystallization or column chromatography, dried and weighed to obtain IM3. Preparation Example 4: Preparation of IM4

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PUM

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Abstract

The invention belongs to the field of medicinal chemistry, and in particular relates to a gatifloxacin derivative and a preparation method and application thereof. In the present invention, the compound shown in formula I is obtained by modifying the structure of the 7-position side chain of gatifloxacin. The compound of the present invention can not only treat the infection caused by Mycobacterium tuberculosis and common bacteria, but also treat bacterial persisters and citrus pathogens. Bacteria, nicotinamide N-methyltransferase (NNMT), interleukin IL-17 PPI and proprotein convertase subtilisin 9 (PCSK9) have inhibitory activity. The preparation process of the compound of the present invention is simple and easy to operate, under mild conditions, and many compounds with enhanced antibacterial activity, improved water solubility, and reduced toxic and side effects can be obtained, which is expected to reduce drug dosage, shorten treatment cycle, and improve patient compliance. New molecular types and research ideas.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a gatifloxacin derivative and its preparation method and application. Background technique [0002] Tuberculosis (TB) is a chronic infectious disease mainly transmitted by respiratory tract caused by Mycobacterium tuberculosis (MTB). Mycobacterium tuberculosis mainly causes tuberculosis, and can also affect all other organs of the human body. It is one of the major diseases that seriously endanger human health, and it is also a long-term global public health and social problem of common concern. During the administration of anti-tuberculosis drugs, due to unreasonable treatment regimens and other reasons, the gene mutation of Mycobacterium tuberculosis occurs, and drug-resistant tuberculosis (DR-TB), especially multi-drug-resistant tuberculosis, is gradually increasing. The prevalence of drug-resistant tuberculosis has even appeared in many countries and regions. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/56C07D401/12C07D417/12A61K31/496A61K31/5377A61P35/00A61P31/04A61P29/00A61P9/00A61P31/06A61P1/04A61P3/06A61P9/10
CPCC07D215/56C07D401/12C07D417/12Y02A50/30
Inventor 杨大成黄敏范莉冯计周刘文谢建平胡军华徐兴然张金坤郭思瑶龙艳玲刘晋宇牟希张泽朝段湘科付彬王帆
Owner SOUTHWEST UNIV
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