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Pyrimidinedione derivatives and methods of use thereof

A technology of compounds and medicinal salts, applied in the direction of drug combinations, active ingredients of heterocyclic compounds, medical preparations containing active ingredients, etc., can solve problems such as diarrhea and skin flushing

Inactive Publication Date: 2010-03-24
SCHERING AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Niacin has also been used to treat metabolic syndrome, but there have been problems with its clinical use, including flushing and diarrhea, even at modest doses

Method used

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  • Pyrimidinedione derivatives and methods of use thereof
  • Pyrimidinedione derivatives and methods of use thereof
  • Pyrimidinedione derivatives and methods of use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0595] Preparation of intermediate compounds 1B and 1C

[0596]

[0597] NaH (1.08 g, 24.70 mmol, 60% in mineral oil) was added to a solution of compound 1A (4.0 g, 23.52 mmol) in DMF / DMSO (30 mL / 20 mL) at room temperature and the resulting mixture was stirred for 40 min . Then n-butyl iodide (2.67 mL, 23.52 mmol) was added and the reaction was stirred at room temperature for about 15 hours. The reaction mixture was then poured into a mixture of EtOAc (250 mL) and 0.5N HCl and the organic phase was washed successively with water (3 times) and brine, then dried (Na 2 SO 4 ), filtered and concentrated in vacuo. The resulting residue was purified using flash column chromatography on silica gel (eluted with hexane / EtOAc (v / v = 1 / 1)) to afford monoalkylated compound 1B (1.4 g, 26%) and dialkylated product 1C ( 1.7 g, 26%). Electrospray MS[M+1] + 240.1.

Embodiment 2

[0599] Preparation of intermediate compound 2B

[0600]

[0601] Step A - Synthesis of Compound 2A

[0602]

[0603] NaH (92.9 mg, 2.12 mmol, 60% in mineral oil) was added to a solution of compound IB (0.4 g, 1.77 mmol) in DMF (3.5 mL) at room temperature and the resulting mixture was stirred for 40 min. Then iodomethane (0.165 mL, 2.65 mmol) was added and the reaction mixture was stirred at room temperature overnight, then poured into a mixture of EtOAc (100 mL) and 0.5N HCl. The organic phase was washed successively with water (3 times) and brine, then dried (Na 2 SO 4 ), filtered and concentrated in vacuo. The resulting residue was purified using silica gel flash column chromatography (eluting with hexane / EtOAc (v / v = 2 / 1 )) to provide compound 2A (0.39 g, 92%).

[0604] Step B - Synthesis of Compound 2B

[0605]

[0606] HNO 3 (0.6mL, fuming) was added dropwise to compound 2A (0.39g, 1.62mmol) in H 2 SO 4 (2.4 mL, 96%) in solution at 0°C. The mixture was ...

Embodiment 3

[0608] Preparation of intermediate compound 3A

[0609]

[0610] Compound 3A was prepared using the method described in Example 2, Step B, substituting Compound 1B for Compound 2A. Electrospray MS[M+1] + 271.1.

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PUM

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Abstract

The present invention relates to pyrimidinedione derivatives, compositions comprising a Pyrimidinedione Derivative and methods for using the Pyrimidinedione Derivatives for treating or preventing a metabolic disorder, dyslipidemia, a cardiovascular disease, a neurological disorder, a hematological disease, cancer, inflammation, a respiratory disease, a gastroenterological disease, diabetes, a diabetic complicaton, obesity, an obesity-related disorder or non-alcoholic fatty liver disease.

Description

field of invention [0001] The present invention relates to pyrimidinedione derivatives, compositions containing pyrimidinedione derivatives and the use of the pyrimidinedione derivatives for the treatment or prevention of metabolic disorders, dyslipidemia, cardiovascular diseases, neurological disorders, blood diseases, cancer, Inflammation, respiratory disease, gastrointestinal disease, diabetes, diabetic complications, obesity, obesity-related conditions, or non-alcoholic fatty liver disease. Background of the invention [0002] Niacin (commonly known as niacin) plays an important role in the production of several sex hormones and stress-related hormones, especially those produced by the adrenal glands. It also plays a role in removing toxic and harmful chemicals from the body. [0003] When taken in large doses, niacin increases blood levels of high-density lipoprotein (HDL), and the drug is sometimes prescribed to patients with low HDL who are at high risk of heart atta...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61K31/519A61K31/522A61P1/00A61P3/00A61P9/00
CPCC07D487/04A61P1/00A61P1/04A61P1/06A61P1/12A61P1/14A61P1/16A61P1/18A61P3/00A61P3/04A61P3/06A61P3/10A61P7/00A61P7/02A61P7/04A61P7/06A61P9/00A61P9/04A61P9/06A61P9/10A61P9/12A61P11/00A61P11/06A61P11/08A61P25/00A61P25/02A61P25/04A61P25/06A61P25/08A61P25/14A61P25/16A61P25/20A61P25/28A61P29/00A61P35/00A61P43/00
Inventor 黄贤海A·帕拉尼R·G·亚斯兰安
Owner SCHERING AG
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