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

Tetrahydro benzothiophene derivative and application thereof to preparation of glycogen synthase kinase 3 beta inhibitor

A technology of benzothiophene and derivatives, applied in the field of medicine, can solve the problems of lack of effective drugs and treatment methods, achieve good GSK-3β inhibitory activity, high activity, and meet the effect of large-scale industrial production

Active Publication Date: 2017-10-17
HARBIN MEDICAL UNIVERSITY
View PDF2 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented inventor describes different types of molecules called gamma hydroxytetraazenoic acids (GHAs). These chemical substances found naturally occur on plants or animals like bacteria or yeast cells but they were discovered later when it was isolated from them. They showed high activities against certain diseases such as Parkinsonism type I diabetes mellitus and dementias caused by Alzheimers syndrome. Additionally, these chemistry made possible use thereof as drugs targeted at specific enzymes involved in cell death processes.

Problems solved by technology

This patented technical problem addressed in this patents relates to finding new ways to effectively treat or prevent Alzheimers diseased through different methods like medications or therapy options.

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
  • Tetrahydro benzothiophene derivative and application thereof to preparation of glycogen synthase kinase 3 beta inhibitor
  • Tetrahydro benzothiophene derivative and application thereof to preparation of glycogen synthase kinase 3 beta inhibitor
  • Tetrahydro benzothiophene derivative and application thereof to preparation of glycogen synthase kinase 3 beta inhibitor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1 Synthesis of intermediate A (2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide)

[0045] Cyclohexanone (0.1mol) and 2-cyanoacetamide (0.1mol) were reacted in ethanol solution (30mL) to obtain compound 3, sulfur powder (0.1–0.11mol) was added to the reacted solution, and diethyl amine (10 mL), and keep the reaction temperature not exceeding 50 °C. After 3 hours of reaction, change to an ice-salt bath to make the reaction liquid crystallize. If there is no crystallization, pour the reaction liquid into 100 mL of water, filter with suction, and recrystallize the precipitated solid with ethanol to obtain the target compound, namely compound 4. Yield 61%.

[0046] Mp 190°C; 1 H-NMR (DMSO-d 6 ): d (ppm) 1.68 (m, 4H), 2.51 (m, 4H), 6.52 (bs, 2H), 6.89 (s, 2H); LRMS-EI: m / z calcd 196.1, found 196.0.

Embodiment 2

[0047] Example 2: Synthesis of GX001 (2-(3-cyclohexylurea)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide)

[0048] Dissolve compound 4 (0.80 mmol) in dry CH 2 Cl 2 (5 mL), add cyclohexyl isocyanate (12.8 mmol) and heat to reflux for 5d. After the reaction solution was cooled, 50% ethanol aqueous solution (5 mL) was added, and suction filtered to obtain the precipitated solid, which was recrystallized with ethanol to obtain the target product with a yield of 79%.

[0049] Mp 190.5-192.5°C; 1 H-NMR (DMSO-d 6 ):d(ppm)1.21(m,4H),1.49(m,6H),1.70(m,4H),2.52(m,4H),3.54(m,1H),6.97(bs,2H),7.53( s,1H),10.48(s,1H); ESI-MS m / z:322.1[M+H] + .

Embodiment 3

[0050] Example 3: Synthesis of GX002 (2-(3-cyclopentylurea)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide)

[0051] Dissolve compound 4 (0.80 mmol) in dry CH 2 Cl 2 (5 mL), add cyclopentyl isocyanate (12.8 mmol) and heat to reflux for 5d. After the reaction solution was cooled, 50% ethanol aqueous solution (5 mL) was added, and suction filtered to obtain the precipitated solid, which was recrystallized with ethanol to obtain the target product with a yield of 61%.

[0052] Mp 200.3-202.5°C; 1 H-NMR (DMSO-d 6 ):d(ppm)1.50(m,4H),1.86(m,4H),1.70(m,4H),2.52(m,4H),3.61(m,1H),6.97(bs,2H),7.53( s,1H),10.48(s,1H); ESI-MS m / z:308.4[M+H] + .

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 discloses a tetrahydro benzothiophene derivative and the application thereof to the preparation of a glycogen synthase kinase 3 beta inhibitor. The tetrahydro benzothiophene derivative, pharmaceutically acceptable salt, optical active body or racemate thereof has a chemical structure as shown in a formula I. Experiments show that the compound has good GSK-3 beta inhibitory activity. In addition, the invention further provides a method for preparing a tetrahydro benzothiophene compound. The method is short in synthesis route, simple in preparation process and easy to operate, and can meet the requirements of large-scale industrial production.

Description

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

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
Owner HARBIN MEDICAL UNIVERSITY
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