Nitroimidazole derivative in therapy

An alkyl and compound technology, applied in the field of nitroimidazole derivatives and pharmaceutical compositions thereof, can solve the problems of discomfort, autoimmune hepatitis, peripheral neuropathy, low water solubility and the like

Inactive Publication Date: 2011-09-28
HC SYNTHETIC PHARMA CO LTD
View PDF4 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is a metaphor for low water solubility, dizziness and gastrointestinal discomfort after taking it, and occ

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Nitroimidazole derivative in therapy
  • Nitroimidazole derivative in therapy
  • Nitroimidazole derivative in therapy

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Embodiment 1: the preparation of compound A

[0053]Dissolve 220g of 1-(3-chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (ornidazole) in 500ml of dichloromethane and slowly add 20% sodium hydroxide 250ML dropwise , stirred and reacted at room temperature for 40 minutes, separated, dried the organic layer, evaporated the solvent under reduced pressure, and the residue was 151g; slowly added 70g of pyrrolidine to the residue in 500ML ethanol solution, reacted at 50°C for 6 hours, terminated the reaction, evaporated under reduced pressure The solution was dried, and the residue was recrystallized with ethanol / ethyl acetate to obtain 92 g of a solid; 92 g of the solid was dissolved in 500 ml of methanol, and 55 g of methyl iodide was added dropwise with stirring, reacted at room temperature until the raw material point disappeared, and evaporated to dryness under reduced pressure to obtain 140 g of compound A.

[0054] Purity: 98.3% Chromatographic conditions C18 chromat...

Embodiment 2

[0063] Example 2: Preparation of Compound B.

[0064] Dissolve 220g of 1-(3-chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole in 500ml of dichloromethane, slowly add 20% sodium hydroxide 250ML dropwise, and stir at room temperature for 40 Minutes, liquid separation, drying of the organic layer, evaporation of solvent under reduced pressure, residue 151g; residue with 500ML ethanol solution, slowly added morpholine 80g, 50 ° C for 10 hours, terminated reaction, solution under reduced pressure, residue Recrystallize with ethyl acetate to obtain 53g of solid; dissolve 53g of solid in 500ml of methanol, add 30g of iodomethane dropwise under stirring, react at room temperature until the raw material point disappears, and evaporate to dryness under reduced pressure to obtain 82g of compound A.

[0065] Purity: 98.1% Chromatographic conditions C18 chromatographic column (250mm×46mm, 5μm), mobile phase is acetonitrile-water (40:60), column temperature is 30°C, detection wavelength is ...

Embodiment 3

[0068] Example 3: Preparation of Compound C.

[0069] Dissolve 220g of 1-(3-chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole in 500ml of dichloromethane, slowly add 20% sodium hydroxide 250ML dropwise, and stir at room temperature for 40 Minutes, liquid separation, drying of the organic layer, evaporation of solvent under reduced pressure, residue 151g; residue with 500ML ethanol solution, slowly added morpholine 80g, 50 ° C for 10 hours, terminated reaction, solution under reduced pressure, residue Recrystallize with ethyl acetate to obtain 53g of solid; dissolve 53g of solid in 500ml of methanol, add 45g of bromopropane dropwise under stirring, react at room temperature until the raw material point disappears, and evaporate to dryness under reduced pressure to obtain 87g of compound C.

[0070] Purity: 97.5% Chromatographic conditions C18 chromatographic column (250mm×46mm, 5μm), mobile phase is acetonitrile-water (40:60), column temperature is 30°C, detection wavelength is...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention relates to a nitroimidazole derivative used in therapy, and provides a compound of formula (I) or its pharmaceutical salt: wherein R1 can be taken as saturated or unsaturated straight chain, branched chain alkyl or cyclic alkyl with the carbon number from 1 to 10, R2, R3 can represent alkyl or form rings, the ring can be the ring from three-membered ring to ten-membered ring, the ring is capable of connecting with one or a plurality of same or different substituents; the rings formed by R2, R3 are capable of forming heterocycles, the heterocycle is capable of containing 0 to 5 same or different heteroatom substitutions; X expresses ion or group with negative electricity, which concretely can be halogen negative ion, organic acid radical, inorganic acid radical. According to the invention, the nitroimidazole derivative is used for treating the diseases caused by anaerobic infection or protozoans infection.

Description

Technical field: [0001] The present invention relates to nitroimidazole derivatives for treatment (especially for the treatment of anaerobic bacteria infection or protozoa infection in humans and other mammals) and their pharmaceutical composition, as well as their preparation method and application. technical background: [0002] Many nitroimidazoles are known. For example: metronidazole, tinidazole, ornidazole, etc. have good antibacterial activity. Ornidazole is a powerful drug against anaerobic bacteria and antiprotozoal infections. It is also a newly developed nitroimidazole derivative after metronidazole with higher curative effect, shorter course of treatment, better tolerance and wider distribution in the body. . The antimicrobial effect of ornidazole is through the reduction of the nitro group in its molecule to an amino group in an oxygen-free environment, or through the formation of free radicals to interact with cell components, resulting in the death of microo...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07D403/06C07D413/06C07D233/95C07C53/10C07C51/41A61K31/4178A61K31/5377A61K31/417A61P31/04A61P33/02
Inventor 杨成强建华施维刘晓鹏张起愿
Owner HC SYNTHETIC PHARMA CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap