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

Benzofuranyl-and benzothienyl-piperazinyl quinolines as 5-serotonin reuptake inhibitors

A technology based on benzofuran and piperazine, which is applied in medical preparations containing active ingredients, organic active ingredients, nervous system diseases, etc.

Inactive Publication Date: 2006-08-02
WYETH LLC
View PDF1 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Such negative feedback limits the increase in synaptic serotonin that can be acutely induced by antidepressants

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
  • Benzofuranyl-and benzothienyl-piperazinyl quinolines as 5-serotonin reuptake inhibitors
  • Benzofuranyl-and benzothienyl-piperazinyl quinolines as 5-serotonin reuptake inhibitors
  • Benzofuranyl-and benzothienyl-piperazinyl quinolines as 5-serotonin reuptake inhibitors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0230] Embodiment 1: Intermediate 1--8-piperazino quinoline

[0231] This intermediate can generally be prepared as described in WO 00 / 40554, which is incorporated herein by reference.

Embodiment 2

[0232] Example 2: Intermediate 2--6-fluoro-8-bromo-quinoline

[0233]

[0234] To a mixture of 7.0 g of 2-bromo-4-fluoro-aniline, 7.0 g of glycerol and 13.0 g of m-nitrobenzenesulfonic acid sodium salt, 20 ml of 70% sulfuric acid was added dropwise. The reaction temperature was raised to 150°C for 4 hours. The resulting mixture was cooled, poured into water, neutralized with NaOH, and the precipitate formed was filtered to yield 34.7 g of 6-fluoro-8-bromo-quinoline. MS (ES) m / z (relative intensity): 227 (M + +H, 100).

Embodiment 3

[0235] Example 3: Intermediate 3--6-fluoro-8-(t-Boc)-piperazino-quinoline

[0236]

[0237] To a mixture of 2.2 g of 6-fluoro-8-bromo-quinoline in THF was added 0.045 g of Pd 2 (dba) 3, 1.3g NaOt-Bu, 0.044g binap, 0.052g tetrakis(triphenylphosphine)palladium(0) and 2.2g t-Boc piperazine. The resulting mixture was refluxed for 3 hours. The reaction mixture was then cooled to room temperature, diluted with ether, filtered through celite and concentrated in vacuo. The crude product was purified by flash chromatography to afford 3.0 g of 6-fluoro-8-(t-Boc)-piperazino-quinoline. MS (ES) m / z (relative intensity): 332 (M + +H, 100).

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

Benzofuranyl-and benzothienyl-piperzinyl quinoline derivatives and compositions containing such compounds are disclosed. Methods of using benzofuranyl- and benzothienyl-piperzinyl quinoline derivatives and compositions containing such composition in the treatment and / or prevention of serotonin-related disorders, such as depression and anxiety, are also disclosed. In addition, processes for the preparation of benzofuranyl- and benzothienyl-piperzinyl quinoline derivatives are disclosed.

Description

[0001] Cross References to Related Applications [0002] This application claims the benefit of Provisional Application Serial No. 60 / 467,368, filed May 2, 2003, the contents of which are hereby incorporated by reference in their entirety. field of invention [0003] The present invention relates to benzofuryl-piperazinylquinoline derivatives or benzothienyl-piperazinylquinoline derivatives, in particular to their use as serotonin reuptake inhibitors and as 5-HT 1A The activity of receptor antagonists, and in particular to their related use in the treatment and / or prevention of serotonin-related diseases. Background of the invention [0004] An estimated 340 million people worldwide suffer from major depressive disorder. Depression is the most frequently diagnosed disorder among mental illnesses, and according to the World Health Organization, it is also the fourth-largest public health problem. If left untreated, depression can have devastating results, disrupting a perso...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/14C07D409/14A61K31/495A61P25/24
Inventor A·M·文卡特桑O·多斯桑托斯M·阿塞林G·T·格罗苏D·A·埃拉德R·E·梅肖K·米格赫
Owner WYETH LLC
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