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Benzoureas having anti-diabetic activity

A compound, phenyl technology, applied in the direction of active ingredients of heterocyclic compounds, organic chemistry, diseases, etc., can solve the problems of negative effects of lipids, inability to significantly improve lipid metabolism, weak efficacy, etc.

Inactive Publication Date: 2007-11-21
MERCK & CO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Another shortcoming of currently marketed PPAR agonists is that monotherapy for type 2 diabetes produces only weak efficacy—a reduction in mean plasma glucose of approximately 20% and hemoglobin A1C from approximately 9.0% to approximately 8.0%
The compounds currently employed do not significantly improve lipid metabolism and can actually have a negative effect on lipids

Method used

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  • Benzoureas having anti-diabetic activity
  • Benzoureas having anti-diabetic activity
  • Benzoureas having anti-diabetic activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0153] The following reaction scheme examples are provided to illustrate the invention and should not be construed as limiting the invention in any way. The scope of the invention is defined by the claims.

[0154] The formulas in Table 1 further illustrate compounds that are made or can be made using the methods disclosed herein.

[0155] The synthesized compounds in Table 1 were analyzed by high pressure liquid chromatography-mass spectrometry (LC-MS) and / or proton NMR. LC-MS samples were analyzed using an Agilent 1100 Series High Pressure Liquid Chromatography coupled to a Waters MicromassZQ mass spectrometer. The column used was Waters Xterra and the compound was eluted using a gradient elution program (10% B to 100% B in 4.5 min) at a flow rate of 2.5 mL / min. Solvent A: water containing 0.06% trifluoroacetic acid. Solvent B: Acetonitrile containing 0.05% trifluoroacetic acid. Retention times are given in minutes.

[0156] Method A: XTerra MS-C18, 4.5 x 50mm, 10-100% ...

Embodiment 1

[0248]

[0249] (5R)-5-(3-{[3-(5-chloro-1,2-benzisoxazol-3-yl)-2-oxo-2,3-dihydro-1H-benzimidazole -1-yl]methyl}phenyl)-5-methyl-1,3-oxazolidine-2,4-dione:

[0250] 1 H NMR (500MHz, CDCl 3 )δ8.39(s, 1H), 8.33(brs, 1H), 7.92(d, 1H), 7.71(s, 1H), 7.61(s, 2H), 7.58(d, 1H), 7.42(m, 2H ), 7.21(d, 2H), 7.02(d, 1H), 5.23(dd, 2H), 1.99(s, 3H).

Embodiment 2

[0252]

[0253] (5R)-5-(4-chloro-3-{[3-(6-methoxy-1,2-benzisoxazol-3-yl)-2-oxo-6-(trifluoromethane Base)-2,3-dihydro-1H-benzimidazol-1-yl]methyl}phenyl)-5-methyl-1,3-oxazolidine-2,4-dione:

[0254] 1 H NMR (500MHz, CDCl 3 )δ8.14(d, 1H), 8.02(d, 1H), 7.67(s, 1H), 7.57(s, 1H), 7.52(d, 1H), 7.26(m, 2H), 7.09(s, 1H ), 7.06(d, 1H), 5.38(s, 2H), 3.98(s, 3H), 1.83(s, 3H).

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PUM

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Abstract

Benzourea compounds of Formula I having aryl-(CH2)x-oxazolidinedione or aryl-(CH2)x-thiazolidinedione substituents on one of the N atoms of the benzourea ring, wherein x is 0 or 1, are PPAR gamma agonists or partial agonists and are useful in the treatment and control of type II diabetes, including hyperglycemia and other symptoms such as dyslipidemia, hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, and obesity, that are often associated with type 2 diabetes.

Description

field of invention [0001] The present invention relates to benzoureas and pharmaceutically acceptable salts and prodrugs thereof, which are useful as therapeutic compounds, in particular for the treatment of type 2 diabetes and conditions often associated with type 2 diabetes, including obesity and lipid disease. Background of the invention [0002] Diabetes is multifactorial and is characterized by increased plasma glucose levels (hyperglycemia) following administration of glucose in the fasted state or during an oral glucose tolerance test. There are generally two recognized forms of diabetes. In type 1 diabetes, or insulin-dependent diabetes mellitus (IDDM), the patient produces little or no insulin, the hormone that regulates glucose utilization. In type 2 diabetes, or non-insulin-dependent diabetes mellitus (NIDDM), insulin is still produced in the body. Patients with type 2 diabetes often have hyperinsulinemia (elevated plasma insulin levels); however, these patient...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/42C07D413/04
CPCC07D413/14A61P1/04A61P3/00A61P3/04A61P3/06A61P3/08A61P3/10A61P5/28A61P5/50A61P9/02A61P9/10A61P9/12A61P9/14A61P15/00A61P17/06A61P19/08A61P25/28A61P27/02A61P29/00A61P35/00A61P43/00
Inventor 刘卫国H·B·伍德刘蔚瑜
Owner MERCK & CO INC
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