Alpha-substituted-2-methyl-5-nitro-diazole-1-alcohol derivative with optical activity

A technology of nitroimidazole and derivatives, which is applied in the field of preparation of anti-anaerobic bacteria drugs, can solve the problems that the optical activity of 2-methyl-5-nitroimidazole-1-ethanol derivatives has not been reported, and achieve good anti-anaerobic bacteria activity.

Inactive Publication Date: 2007-06-20
NANJING SANHOME PHARMACEUTICAL CO LTD
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  • Abstract
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Problems solved by technology

The Chinese patent application whose publication number is CN1605586A discloses α-substituted 2-methyl-5-nitroimidazole-1-ethanol derivatives and their preparation methods and uses, but for α-substituted 2-methyl-5- The optical activity of nitroimidazole-1-ethanol derivatives has not been reported

Method used

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  • Alpha-substituted-2-methyl-5-nitro-diazole-1-alcohol derivative with optical activity
  • Alpha-substituted-2-methyl-5-nitro-diazole-1-alcohol derivative with optical activity
  • Alpha-substituted-2-methyl-5-nitro-diazole-1-alcohol derivative with optical activity

Examples

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Embodiment 1

[0037] Preparation of S-(-)-1-(2,3-epoxypropyl)-2-methyl-5-nitroimidazole

[0038] Add 100g (0.45mol) S-(-)-1-(3-chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole and 200ml ethanol into the reaction flask, and cool to 5~ At 10°C, 270ml (0.68mol) of 10% NaOH aqueous solution was added dropwise, and the temperature was kept below 20°C for 30 minutes after the drop was completed. After the reaction, the reaction solution was poured into 200 ml of water, extracted with ethyl acetate, and the organic layers were combined and dried over anhydrous magnesium sulfate. Filter and evaporate to dryness under reduced pressure to obtain 81.5 g of oily substance. [α] D 20 =-27.7° (C=1.0, ethanol)

Embodiment 2

[0040] Preparation of R-(-)-1-(2-methyl-5-nitroimidazol-1-yl)-3-morpholinopropan-2-ol

[0041] Heat 10g (54.6mmol) S-(-)-1-(2,3-epoxypropyl)-2-methyl-5-nitroimidazole, 80ml methanol, and 4.7ml (54mmol) morpholine under reflux for 3h , slightly cooled, evaporate methanol under reduced pressure, add 80ml of water to the residue, extract with ethyl acetate, combine organic layers, and dry over anhydrous magnesium sulfate. Filter, and distill off ethyl acetate under reduced pressure to obtain an oil. Dissolve the oil in 200ml of ethanol and pass through dry HCl gas to precipitate a solid, which is filtered and dried to obtain the hydrochloride. The hydrochloride was dissolved in 200ml of water, adjusted to PH=8 with 10% NaOH, extracted with ethyl acetate, and the combined organic layers were dried over anhydrous magnesium sulfate. Filter and evaporate to dryness under reduced pressure to obtain an oil. Place to crystallize to obtain 8.5 g of solid. Yield: 57.8%, mp: 82-84°C, [...

Embodiment 3

[0048] Preparation of R-(+)-1-(2,3-epoxypropyl)-2-methyl-5-nitroimidazole

[0049] Add 100g (0.45mol) R-(+)-1-(3-chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole and 200ml ethanol into the reaction flask, and cool to 5~ At 10°C, 270ml (0.68mol) of 10% NaOH aqueous solution was added dropwise, and the temperature was kept below 20°C for 30 minutes after the drop was completed. After the reaction, the reaction solution was poured into 200 ml of water, extracted with ethyl acetate, and the organic layers were combined and dried over anhydrous magnesium sulfate. Filter and evaporate to dryness under reduced pressure to obtain 81.5 g of oily substance. [α] D 20 =+28.6° (C=1.0, ethanol)

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Abstract

Laevo isomer and dextroisomer of alpha-substituted 2-methyl-5-nitrodazole-1-ethanol derivative, its production, medicinal composition containing the derivative or its solvent or accepted salt and use for preparing anti-anaerobe medicine are disclosed.

Description

technical field [0001] The present invention relates to an optically active α-substituted 2-methyl-5-nitroimidazole-1-ethanol derivative and a preparation method thereof, and also relates to a pharmaceutical composition containing the derivative, and its preparation for anti-anaerobe drugs use. Background technique [0002] 2-Methyl-5-nitazole imidazole derivatives have good anti-anaerobe activity, and many preparation methods have been disclosed. The Chinese patent application whose publication number is CN1605586A discloses α-substituted 2-methyl-5-nitroimidazole-1-ethanol derivatives and their preparation methods and uses, but for α-substituted 2-methyl-5- The optical activity of nitroimidazole-1-ethanol derivatives has not been reported. Contents of the invention [0003] The object of the present invention is to provide an optically active α-substituted 2-methyl-5-nitroimidazole-1-ethanol derivative (compound of general formula I), that is, α-substituted 2-methyl-5-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/12C07D401/12C07D413/12A61K31/4178A61K31/435A61P31/00
Inventor 张仓张文萍宋海斌
Owner NANJING SANHOME PHARMACEUTICAL CO LTD
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