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

Indanyloxydihydrobenzofuranylacetic acids

a technology of indanyloxydihydrobenzofuranylacetic acid and indanyloxydihydrobenzofuranylacetic acid, which is applied in the field of new drugs, can solve the problems of diabetes, impaired beta cell function, and increased blood glucose levels, and achieves the effects of reducing the risk of cardiovascular diseas

Inactive Publication Date: 2014-06-12
BOEHRINGER INGELHEIM INT GMBH
View PDF0 Cites 39 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention relates to certain compounds that can modulate GPR40, a receptor in the body. These compounds have advantages such as being more potent, stable, and soluble. The invention aims to provide new compounds that can be used for the development of new treatments for metabolic and inflammatory diseases.

Problems solved by technology

The amount of insulin produced by the remaining pancreatic islet cells is too low, resulting in elevated blood glucose levels (hyperglycemia).
High blood glucose levels (and also high blood lipid levels) in turn lead to an impairment of beta cell function and to an increase in beta cell apoptosis.
Diabetes is a very disabling disease, because today's common anti-diabetic drugs do not control blood sugar levels well enough to completely prevent the occurrence of high and low blood sugar levels.
Out of range blood sugar levels are toxic and cause long-term complications for example retinopathy, renopathy, neuropathy and peripheral vascular disease.
Obesity is associated with an increased risk of follow-up diseases such as cardiovascular diseases, hypertension, diabetes, hyperlipidemia and an increased mortality.
These often occur in the same patients and are major risk factors for development of diabetes type II and cardiovascular disease.

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
  • Indanyloxydihydrobenzofuranylacetic acids
  • Indanyloxydihydrobenzofuranylacetic acids
  • Indanyloxydihydrobenzofuranylacetic acids

Examples

Experimental program
Comparison scheme
Effect test

example 1

[(S)-6-{(R)-7-Fluoro-4-[4-(2-methoxy-ethoxy)-phenoxy]-indan-1-yloxy}-2,3-dihydro-benzofuran-3-yl]-acetic acid

[0529]

[0530]1 M aqueous NaOH solution (0.7 mL) is added to a solution of [(S)-6-{(R)-7-fluoro-4-[4-(2-methoxy-ethoxy)-phenoxy]-indan-1-yloxy}-2,3-dihydro-benzofuran-3-yl]-acetic acid methyl ester (62 mg) in methanol (2 mL) and tetrahydrofuran (2 mL) at room temperature. The mixture is stirred at room temperature for 6 h. The organic solvent is evaporated, water is added, and the resulting mixture is neutralized with 1 M aqueous HCl solution (0.7 mL). The solution is stirred at room temperature for 0.5 h.

[0531]The precipitate is separated by filtration, washed with water and dried to give the title compound. LC (method 3): tR=0.39 min; Mass spectrum (ESI−): m / z=493 [M−H]−.

example 2

[(S)-6-{(R)-7-Fluoro-4-[4-(3-hydroxy-3-methyl-butoxy)-phenoxy]-indan-1-yloxy}-2,3-dihydro-benzofuran-3-yl]-acetic acid

[0532]

[0533]The title compound is prepared from [(S)-6-{(R)-7-fluoro-4-[4-(3-hydroxy-3-methyl-butoxy)-phenoxy]-indan-1-yloxy}-2,3-dihydro-benzofuran-3-yl]-acetic acid methyl ester following a procedure analogous to that described for Example 1. LC (method 3): tR=0.41 min; Mass spectrum (ESI−): m / z=521 [M−H]−.

example 3

[(S)-6-{(R)-7-Fluoro-4-[4-(2-hydroxy-2-methyl-propoxy)-phenoxy]-indan-1-yloxy}-2,3-dihydro-benzofuran-3-yl]-acetic acid

[0534]

[0535]The title compound is prepared from [(S)-6-{(R)-7-fluoro-4-[4-(2-hydroxy-2-methyl-propoxy)-phenoxy]-indan-1-yloxy}-2,3-dihydro-benzofuran-3-yl]-acetic acid methyl ester following a procedure analogous to that described for Example 1. LC (method 3): tR=0.35 min; Mass spectrum (ESI+): m / z=531 [M+Na]+.

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

PropertyMeasurementUnit
Forceaaaaaaaaaa
Forceaaaaaaaaaa
Pressureaaaaaaaaaa
Login to View More

Abstract

The present invention relates to compounds of general formula I,wherein the groups (Het)Ar and R1 are defined as in claim 1, which have valuable pharmacological properties, in particular bind to the GPR40 receptor and modulate its activity. The compounds are suitable for treatment and prevention of diseases which can be influenced by this receptor, such as metabolic diseases, in particular diabetes type 2.

Description

FIELD OF THE INVENTION[0001]The present invention relates to novel indanyloxydihydrobenzofuranylacetic acids, that are agonists of the G-protein coupled receptor 40 (GPR40, also known as free fatty acid receptor FFAR 1), to processes for their preparation, to pharmaceutical compositions containing these compounds and to their medical use for the prophylaxis and / or treatment of diseases which can be influenced by the modulation of the function of GPR40. Particularly, the pharmaceutical compositions of the invention are suitable for the prophylaxis and / or therapy of metabolic diseases, such as diabetes, more specifically type 2 diabetes mellitus, and conditions associated with the disease, including insulin resistance, obesity, cardiovascular disease and dyslipidemia.BACKGROUND OF THE INVENTION[0002]Metabolic diseases are diseases caused by an abnormal metabolic process and may either be congenital due to an inherited enzyme abnormality or acquired due to a disease of an endocrine org...

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): A61K31/5377A61K31/343A61K31/4025C07D405/12A61K45/06A61K31/41C07D405/14A61K31/443A61K31/4155C07D307/80A61K31/4178
CPCC07D407/12C07D413/12C07D417/12A61K31/085A61K31/192A61K31/34A61K31/09C07D401/12A61K45/06C07D307/80C07D405/12C07D405/14A61P3/00A61P3/04A61P3/06A61P43/00A61P9/00A61P9/04A61P9/10A61P9/12A61P3/10A61K31/506A61K31/497A61K31/343A61K31/4025A61K31/41A61K31/4155A61K31/4178A61K31/443A61K31/5377A61K31/351A61K31/357A61K31/36A61K31/404A61K31/416A61K31/4196A61K31/422A61K31/4245A61K31/427A61K31/4709
Inventor ECKHARDT, MATTHIASFRATTINI, SARALANGKOPF, ELKEWAGNER, HOLGER
Owner BOEHRINGER INGELHEIM INT GMBH
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