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Family of aryl, heteroaryl, O-aryl and O-heteroaryl carbasugars

A group, alkyl technology, applied in the field of treatment or prevention of diabetes and obesity, can solve problems that have not been exemplified

Active Publication Date: 2014-03-19
TFCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] O-aryl and aryl analogues have also been reported in WO2009 / 076550, in which the ring oxygen is replaced by a carbon atom carrying 2 halogen atoms, but have not been exemplified

Method used

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  • Family of aryl, heteroaryl, O-aryl and O-heteroaryl carbasugars
  • Family of aryl, heteroaryl, O-aryl and O-heteroaryl carbasugars
  • Family of aryl, heteroaryl, O-aryl and O-heteroaryl carbasugars

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Experimental program
Comparison scheme
Effect test

Embodiment

[0343] 1. Preparation of the compound of the present invention

[0344] Abbreviations encountered in the text are defined as follows:

[0345] Acetyl

[0346] ADDP Dipiperidine azodicarboxylate

[0347] Bn benzyl

[0348] cat. Catalytic

[0349] DAST diethylaminosulfur trifluoride

[0350] DCM dichloromethane

[0351] de diastereomeric excess

[0352] DMAP 4-Dimethylaminopyridine

[0353] DMF Dimethylformamide

[0354] DMSO Dimethyl Sulfoxide

[0355] eq. Equivalent

[0356] ESI electrospray ionization

[0357] g grams

[0358] Hz hertz

[0359] mg mg

[0360] MHz megahertz

[0361] min. minute

[0362] mL milliliter

[0363] mmol millimole

[0364] mM millimole / liter

[0365] μmol micromole

[0366] nmol Nanomole

[0367] NMR nuclear magnetic resonance

[0368] oral

[0369] PEG polyethylene glycol

[0370] QS appropriate amount

[0371] Rf blocker

[0372] rt room temperature

[0373] TFAA Trifluoroacetic anhydride

[0374] THF Tetrahydrofuran

...

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PUM

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Abstract

The present invention relates to a compound of the following formula (I): as well as its process of preparation, pharmaceutical and cosmetics composition comprising it and use thereof, notably as an inhibitor of the sodium-dependent glucose co-transporter protein, such as SGLTl, SGLT2 and SGLT3, in particular in the treatment or prevention of diabetes, and more particularly type-II diabetes, diabetes-related complications, such as arthritis of the lower extremities, cardiac infarction, renal insufficiency, neuropathy or blindness, hyperglycemia, hyperinsulinemia, obesity, hypertriglyceridemia, X syndrome and arteriosclerosis, as well as for its use as an anticancer, anti-infective, anti-viral, anti-thrombotic or anti-inflammatory drug, or for lightening, bleaching, depigmenting the skin, removing blemishes from the skin, particularly age spots and freckles, or preventing pigmentation of the skin.

Description

technical field [0001] The present invention relates to a family of fluorinated aryl, heteroaryl, O-aryl, O-heteroaryl glycosides, processes for their preparation, and their use in the field of medicine or cosmetics, in particular for the treatment or prevention of diabetes and obesity, and as a depigmentation or lightening agent. Background technique [0002] Sugars and their derivatives constitute one of the most common classes of compounds found in nature. Based on its chemical structure, it exhibits various physicochemical properties and can play key roles in many biological processes. [0003] In recent years, there has been an increasing interest in the discovery of novel glycosides with favorable properties in terms of improved potency, selectivity and stability. [0004] Among these compounds, especially aryl glycosides or phenolic glycosides are found to be useful in the field of cosmetics or for the treatment or prevention of diseases such as diabetes, obesity, c...

Claims

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Application Information

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IPC IPC(8): C07C43/225C07C43/23C07C43/247C07C43/253C07D231/20C07D333/16A61K31/085A61K31/415A61K31/381A61P3/04A61P3/10A61P35/00A61P29/00A61P31/00A61P31/12
CPCC07D333/16C07C43/225A61K8/4986A61K8/494C07C43/23C07C43/29C07C41/09C07C43/253C07D231/20C07C43/247A61Q19/02C07C41/22C07C41/24A61K8/347A61K8/33C07C2601/14A61K8/4946A61K8/69A61P13/00A61P13/12A61P19/02A61P25/00A61P27/02A61P29/00A61P3/00A61P3/04A61P31/00A61P31/12A61P35/00A61P3/06A61P43/00A61P7/02A61P9/10A61P3/10A61K31/085A61K31/381A61K31/415
Inventor G·德利安古-戈德弗鲁瓦L·洛佩斯
Owner TFCHEM
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