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C-4''-substituted macrolide compound

A technology of compounds and hydrates, applied in the direction of sugar derivatives, organic chemistry, antibacterial drugs, etc., can solve the problems of unstable dynamics in vivo and achieve good antibacterial activity

Inactive Publication Date: 2017-04-19
TAISHO PHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, erythromycin is decomposed by gastric acid, so there is a disadvantage of unstable kinetics in vivo

Method used

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  • C-4''-substituted macrolide compound

Examples

Experimental program
Comparison scheme
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Embodiment

[0040]Hereinafter, the present invention will be further described in detail through reference examples, examples, and test examples. The method for synthesizing the compound of the present invention is not limited to the following methods, and methods known to those skilled in the art, such as switching the order of the steps and protecting and deprotecting functional groups, can also be used.

[0041] Each equipment data of following reference example, embodiment record is measured by following measurement equipment;

[0042] NMR spectrum: JEOL Ltd. JNM-ECA600 (600MHz), JEOL Ltd. JNM-ECA500 (500MHz)

[0043] MS spectrum: Shimadzu Corporation LCMS-2010EV or Micromass Company Platform LC.

[0044] In the following reference examples and examples, high-performance liquid chromatography-mass spectrometry (LCMS) is determined by the following conditions;

[0045] Determination equipment: Agilent 2900 and Agilent 6150

[0046] Column: Waters (Waters) Acquity CSH C18, 1.7μm, φ2....

reference example 1

[0066] Reference Example 1 Synthesis of N,N-diisopropyl-N-methylethane-1,2-diamine

[0067]

[0068]

[0069] To 135 mL of a methanol solution of 8.9 mol / L methylamine, 72 mL of a methanol solution of 24.0 g of diisopropylaminochloroethane hydrochloride was added dropwise under ice-cooling, and stirred at room temperature for 20 minutes. The reaction liquid was concentrated under reduced pressure, the obtained residue was dissolved in chloroform, and a 2 mol / L sodium hydroxide aqueous solution was added under ice-cooling. The reaction solution was extracted twice with chloroform, the organic layer was concentrated under reduced pressure, and the resulting residue was purified by amino silica gel column chromatography (hexane:chloroform=5:1 to chloroform only) to obtain 19.4 g of the title compound;

[0070] MS(ESI) m / z= 159 [M+H]+

[0071] 1H-NMR (400 MHz, CDCl 3 ) δ(ppm) : 0.99 (d, J=1.71 Hz, 6 H) 1.00 (d, J=1.71Hz, 6 H) 2.43 (s, 3 H) 2.54 -2.57 (m, 4 H) 2.96 -3.03 ( ...

reference example 2

[0072] Reference example 2 Synthesis of 2-amino-N-ethylacetamide

[0073]

[0074]

[0075] (1) Add 108mL of 70% ethylamine aqueous solution to 1.0L of N-(benzyloxycarbonyl)glycine 209g in chloroform, and add 1-ethyl-3-(3-dimethylaminopropyl) carbon under ice-cooling conditions After adding 249 g of diimine hydrochloride, it was stirred overnight at room temperature. Saturated aqueous sodium bicarbonate solution was added to the reaction liquid, followed by extraction with chloroform. The organic layer was concentrated under reduced pressure, the obtained residue was suspended in 400 mL of ethyl acetate, 200 mL of hexane was added and stirred, and the generated solid was collected by filtration to obtain 150 g of an amide compound.

[0076]

[0077]

[0078] (2) 15 g of 10% palladium carbon was added to 630 mL of methanol solution of 150 g of the amide compound obtained in Reference Example 2-(1) above, and stirred at room temperature for 6 days under a hydrogen atm...

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Abstract

A compound of the following formula [1], which possesses good antimicrobial activity against erythromycin-resistant bacteria, such as resistant pneumococci, streptococci and mycoplasma, against which conventional macrolide antibiotics do not possess sufficient antimicrobial activity. Also provided is a pharmaceutically acceptable salt thereof, or a hydrate or solvate thereof.

Description

technical field [0001] The present invention relates to novel antibiotics with erythromycin-like skeletons. More specifically, the present invention relates to a macrolide compound containing a methyl group substituted by a nitrogen-containing substituent at the 4" position of cladinose as an active ingredient for the prevention and / or treatment of infectious diseases medicine. Background technique [0002] Erythromycin A is an antibiotic widely used as a therapeutic drug for infectious diseases caused by Gram-positive bacteria, mycoplasma, and the like. However, erythromycin is decomposed by gastric acid, so it has the disadvantage of unstable kinetics in vivo. Accordingly, derivatives with increased stability to acids were investigated, and as a result, macrolide drugs that were dynamically stable in vivo, such as clarithromycin, azithromycin (Patent Documents 1 and 2), and roxithromycin, were developed. These macrolide drugs that treat respiratory infectious diseases i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/08A61K31/7048A61P31/04
CPCC07H17/08A61P31/04
Inventor 杉本智洋林真知河口尚则
Owner TAISHO PHARMACEUTICAL CO LTD
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