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C-aryl glucoside SGLT2 inhibitors and method

A technology of inhibitors and reagents, applied in the direction of carbocyclyl sugars, sugar derivatives, pharmaceutical formulations, etc., can solve the problems of exacerbated peripheral insulin resistance, low blood sugar, glucose absorption damage, etc.

Inactive Publication Date: 2005-08-10
ASTRAZENECA AB
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Concomitant inhibition of glucose-facilitating transporter (GLUT) is not desirable as such inhibitors are thought to exacerbate peripheral insulin resistance and also cause hypoglycemia in the CNS
Inhibition of SGLT1 can also have serious adverse consequences such as the genetic syndrome glucose / galactose malabsorption (GGM), in which mutations in the SGLT1 cotransporter lead to impaired intestinal glucose absorption and life-threatening diarrhea and dehydration

Method used

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  • C-aryl glucoside SGLT2 inhibitors and method
  • C-aryl glucoside SGLT2 inhibitors and method
  • C-aryl glucoside SGLT2 inhibitors and method

Examples

Experimental program
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Effect test

Embodiment

[0196]

[0197] A. 5-Bromo-2-chloro-4'-ethoxybenzophenone

[0198] Commercially available 5-bromo-2-chlorobenzoic acid (250 g, 1.06 mol) was added to 450 ml of CH containing oxalyl chloride (1.1 mol) 2 Cl 2 , stirred to make a suspension, and then added 1.5ml DMF to it. Once the evolution of gas ceased, the reaction was stirred overnight, then the volatiles were removed under vacuum using a rotary evaporator. Dissolve the crude 5-bromo-2-chlorobenzoyl chloride in 200 ml CH 2 Cl 2 , the yellow solution was transferred to a 2 L three-necked flask equipped with an overhead stirrer and an internal thermometer. The stirred mixture was cooled to -3°C, then phenetole (130 g, 1.08 mol) was added. Gradually add AlCl over a period of 30 min via the solids addition funnel 3 (140 g, 1.07 mol) to ensure that the temperature does not exceed 4°C. After adding 60% AlCl 3 A large amount of HCl gas which then started to be evolved was absorbed by the stirred concentrated NaOH solutio...

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Abstract

An SGLT2 inhibiting compound is provided having the formula A method is also provided for treating diabetes and related diseases employing an SGLT2 inhibiting amount of the above compound alone or in combination with another antidiabetic agent or other therapeutic agent.

Description

[0001] This application is a continuation-in-part of U.S. Patent Application Serial No. 09 / 679,027, filed October 4, 2000, which claims priority from Application No. 60, filed April 5, 2000 U.S. Provisional Application No. 60 / 158,773 filed October 12, 1999. technical field [0002] The present invention relates to C-aryl glucosides, which are inhibitors of the sodium-dependent glucose transporter (SGLT2) found in the intestine and kidney, and to the use of such C-aryl glucosides alone or using such C-aryl glucosides and one, two or more other types of antidiabetic agents and / or one, two or more other types of therapeutic agents such as lipid-lowering agents in combination (combination) to Methods of treating diabetes, especially type 2 diabetes, and hyperglycemia, hyperinsulinemia, obesity, hypertriglyceridemia, syndrome X, diabetic complications, atherosclerosis and related diseases. Background technique [0003] About 100 million people in the world suffer from type II di...

Claims

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Application Information

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IPC IPC(8): C07H7/04A61K31/155A61K31/22A61K31/351A61K31/365A61K31/70A61K31/7034A61K45/00A61K45/06A61P3/04A61P3/06A61P3/10A61P5/48A61P9/10A61P9/12A61P13/12A61P17/02A61P25/00A61P27/00C07C43/225C07C45/46C07C49/84C07D309/10C07H15/20C07H15/203
CPCA61K31/7034C07C49/84C07H7/04C07C45/46C07H15/203C07C43/225A61K45/06A61K31/70C07D309/10A61P13/12A61P17/02A61P25/00A61P25/28A61P27/00A61P27/02A61P3/00A61P3/04A61P3/06A61P43/00A61P5/00A61P5/48A61P7/02A61P9/10A61P9/12A61P3/10A61K2300/00C07H15/20
Inventor B·埃尔斯沃斯W·N·沃什伯恩P·M·谢尔G·吴W·孟
Owner ASTRAZENECA AB
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