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Quinolone compound containing oximino, and its preparing method and use

A compound, quinolone technology, applied in the fields of medicinal chemistry and chemotherapeutics, which can solve problems such as excluding piperidinyl groups

Inactive Publication Date: 2006-10-25
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, none of the above-mentioned compounds include piperidinyl having both an oxime group and an aminomethyl group or an alkyl-substituted amino group at the 7-position.

Method used

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  • Quinolone compound containing oximino, and its preparing method and use
  • Quinolone compound containing oximino, and its preparing method and use
  • Quinolone compound containing oximino, and its preparing method and use

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0087] Synthesis of Methyl 1-(2-cyano-ethylamino)propionate

[0088]

[0089] Methyl 1-alanine (103.1 g 1 mol) (Tetrahedron. Lett. 42.21.2001.3525-3528) was dissolved in 300 ml of methanol, and acrylonitrile (63.7 g, 1.2 mol) was added. The reaction mixture was stirred under reflux for 5 hours, and the solvent was removed. The residue was distilled under reduced pressure (110-130°C / 10.0 Torr) to obtain 64.2 g (yield 42.0%) of the title compound. 1 H NMR (CDCl 3 , ppm): δ 3.59 (3H, s), 2.82 (4H, q), 2.42 (4H, t). MS (EI, m / e): 156 (M + )

preparation example 2

[0091] Synthesis of 3-cyano-1-(N-tert-butoxycarbonyl)-piperidin-4-one

[0092]

[0093]In the above formula and the following formulas, Boc represents tert-butoxycarbonyl. The compound (29.0 g, 0.186 mol) obtained in Preparation Example 1 was dissolved in 200 ml of chloroform, di-tert-butoxycarbonyl dicarbonate (45.0 g, 1.1 mol equivalent) was added thereto, and the reaction mixture was stirred at room temperature for 17 hours . The reaction solution was concentrated, and the residue was diluted with 250 ml of absolute ethanol. The resulting solution was added to a sodium ethoxide solution prepared by adding metallic sodium (Na) (10.7 g, 2.5 mol equivalents) to 220 ml of absolute ethanol under heating to reflux. After the addition was complete, the reaction was continued for an additional hour under reflux. The reaction solution was concentrated under reduced pressure, and the residue was diluted with water and washed with dichloromethane. The organic layer was separate...

preparation example 3

[0095] Synthesis of 3-methyl-3-cyano-1-(N-tert-butoxycarbonyl)-piperidin-4-one

[0096]

[0097] The compound (2.24 g, 10 mmol) prepared in Preparation Example 2 and tetrahydrofuran solution (12 ml, 1 mol / L, 1.2 mol equivalent) of tetra-n-butylammonium fluoride (TBAF) were dissolved in 100 ml of tetrahydrofuran. To which was added iodomethane (CH 3 I) (2.82 g, 2 mol equivalents). The reaction mixture was stirred overnight at room temperature. The reaction solution was concentrated, and the residue was dissolved in 200 ml of ethyl acetate, washed with water, washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated, and the crude product was subjected to column chromatography (ethyl acetate:petroleum ether=1:10) to obtain 1.49 g (yield 63.0%) of the title compound. 1 H NMR (CDCl 3 , ppm): δ4.2 (2H, m), 3.4-2.5 (4H, m), 1.45 (9H, s), 1.4 (3H, s). MS (EI, m / e): 238 (M + )

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Abstract

This invention discloses quinolone category compound contains hydroximino and its medical used acceptable iorganic or organic salt, and their solvate and preparation method. This kind of compound is tested by several kinds of strains to prove their activity to the strains; it can be used to medicin that used to cure diseasebrought by gel an shi negative and positive bacterium.

Description

technical field [0001] The invention relates to the fields of medicinal chemistry and chemotherapeutics, in particular to the synthesis of quinolone compounds and their use in the preparation of drugs for treating infectious diseases. Background technique [0002] In 1962, Nalidixic acid was synthesized by Lesher et al., and a new class of antibacterial drugs appeared (J Med Pharm Chem 1962, 5: 1063-1065). In 1982, ciprofloxacin, the first quinolone drug used outside the urinary system, went on the market [Drugs1996, 51(6): 1019-1074], which represented that this type of new antibacterial drug entered a new stage. Since then, the basic quinolone mother ring has become the starting point for new fluoroquinolone structure optimization. After more than 40 years of development, more than 20 varieties of quinolones have been widely used in clinical practice, and they are currently one of the main antibacterial drugs in clinical use. [0003] Some new fluoroquinolones such as Gat...

Claims

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Application Information

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IPC IPC(8): C07D471/04A61K31/4375A61K31/438A61P31/04C07D401/04
CPCY02P20/582
Inventor 杨玉社党昭李战嵇汝运
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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