Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Imidazolone-morphinan as well as preparation method and application thereof

A technology of morphinan and imidazolone, applied in the field of imidazolone-morphinan and preparation thereof, can solve the problems that have not been seen before and the like

Active Publication Date: 2016-06-29
INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI +1
View PDF3 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The imidazolone-morphinan compound of the present invention and its anti-Parkinson effect, so far, have not yet seen relevant reports at home and abroad

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
  • Imidazolone-morphinan as well as preparation method and application thereof
  • Imidazolone-morphinan as well as preparation method and application thereof
  • Imidazolone-morphinan as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] 《Example 1》Synthesis of imidazolone-morphinan

[0026] The method for said imidazolone-morphinan, its basic synthetic route is: dextromethorphan reacts with boron tribromide to generate nordextromethorphan, then reacts with nitric acid for nitration, then reacts with trifluoromethanesulfonic anhydride and trifluoromethanesulfonic anhydride Ethylamine reacts, then reacts with benzylamine, and then catalyzes hydrogenation reaction by palladium hydroxide carbon to generate diamine compound, then reacts with N,N'-carbonyldiimidazole to generate imidazolone-N-methylmorphinan, and finally React with pyridine hydrochloride to generate imidazolone-morphinan.

[0027] 1. Preparation of Dextromethorphan

[0028] 50.00g of dextromethorphan hydrobromide was dissolved in 300mL of water to form a white suspension. Adjust the pH to 8-9 with an appropriate amount of sodium carbonate, and a large amount of white solids were precipitated. It was extracted three times with dichlorometha...

Embodiment 2

[0043] "Example 2" Anti-inflammatory activity and cell viability experiment of imidazolone-morphinan

[0044] BV2 microglial cells (Cell Resource Center, Institute of Basic Medical Sciences, Chinese Academy of Medical Sciences), incomplete medium (DMEM) (Hyclone, USA), newborn fetal bovine serum (FBS) (GIBCOBRLproduct, Grand Island, N.Y.USA), lipopolysaccharide ( LPS), naphthalene ethylenediamine solution, p-aminobenzenesulfonic acid (Sigma, USA).

[0045] Positive control drug: 3-HM (Sigma, USA).

[0046] Anti-inflammatory activity experiment of compounds based on LPS-activated microglial neuroinflammation model

[0047] BV2 cells were cultured in DMEM medium containing 10% newborn bovine serum at 37°C, 5% CO 2 Grow at 95% air, 100% relative humidity. The BV2 cells in the logarithmic growth phase were counted and divided into 5×10 3 Each well was inoculated into a 96-well plate, and after culturing for 24 hours, the screened drug and positive control drug 3-HM (10 -5 , 1...

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 imidazolone-morphinan and an application thereof. A research result indicates that imidazolone-morphinan has anti-inflammatory activity in an inhibition model experiment for inflammatory factors released by LPS (lipopolysaccharide) activated microglia BV2, does not show up cytotoxicity, is expected to be a candidate drug for prophylactic treatment of Parkinson's disease and has good development prospect.

Description

Technical field: [0001] The invention belongs to the field of medicine, and relates to imidazolone-morphinan and its preparation method and application. Background technique: [0002] Parkinson's disease (PD) is the second most common neurodegenerative disease after Alzheimer's disease. According to the statistics of the National PD Foundation in 2013, the etiology and pathogenesis have not yet been clarified. The pathological features are the degeneration of dopaminergic neurons in the compact part of the substantia nigra in the patient's brain, the reduction in the content of dopamine neurotransmitter synthesized by the remaining neurons in the striatum, and the low function of the dopaminergic neurons in the nigrostriatum and the relative function of the cholinergic neurons. Predominant, resulting in movement disorders [Olanow, C.; Tatton, W.; Etiology and pathogenesis of Parkinson's disease [J]. AnnuRevNeurosci, 1999, 22 (1), 123-144; Jellinger, K.A. 2002, (62), 347-76]...

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): C07D471/08A61K31/439A61P25/16
CPCC07D471/08
Inventor 张丹王玉成李子强鲍秀琦白晓光张国宁王菊仙周磊李强郑远鹏臧彩霞
Owner INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com