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Compound with substituted cyclopropane structure, production method and medicine use thereof

A kind of cyclopropane and compound technology, applied in the field of a class of compounds with substituted cyclopropane structure, preparation and medical use thereof

Inactive Publication Date: 2008-06-11
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Except for GLP-1 and its peptide analogues, there are no reports on the successful development of non-peptide small molecule GLP-1R agonists

Method used

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  • Compound with substituted cyclopropane structure, production method and medicine use thereof
  • Compound with substituted cyclopropane structure, production method and medicine use thereof
  • Compound with substituted cyclopropane structure, production method and medicine use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0162] NMR calibration: δH / C 7.26 / 77.0ppm (CDCl3); δH / C 2.50 / 39.51ppm (DMSO-d6).

[0163]

[0164]Compound 2,3-diaminosuccinic acid was dissolved in an appropriate amount of 5% sodium hydroxide solution, cooled to 0°C, p-BocNH benzoyl chloride (2.5eq) was added dropwise, left at room temperature overnight, acidified to pH=2 with hydrochloric acid, Extracted with ether and concentrated to dryness. Recrystallization from ethanol / water afforded the amide.

[0165] The above amide (1eq) was dissolved in methanol, a few drops of concentrated sulfuric acid were added dropwise, and heated to reflux for 8 hours to obtain the ester.

[0166] The above ester and thionyl chloride were heated and reacted for 2 hours to obtain a ring compound.

[0167] The above compound (2eq) was heated to 180°C under the protection of nitrogen, and phenyldiazomethane (1eq) was slowly added dropwise at a rate to maintain the reaction temperature at 180°C-190°C. Cooling gave an orange residue. Add a...

Embodiment 2

[0173]

[0174] Dissolve the raw material acid (1eq) in methanol, add a few drops of concentrated sulfuric acid, and heat to reflux for 8 hours to obtain the ester.

[0175] The above ester (2eq) was heated to 180°C under the protection of nitrogen, and the compound phenyldiazomethane (1eq) was slowly added dropwise at a rate to maintain the reaction temperature at 180°C-190°C. Cooling gave an orange residue. An appropriate amount of 10% ether / n-pentane was added and filtered to obtain a compound with a substituted cyclopropane structure.

[0176] Dissolve the above-mentioned compound having a substituted cyclopropane structure in methanol, add sodium hydroxide solution, heat and hydrolyze to obtain a product.

[0177] The same method obtains the following products:

[0178]

[0179]

Embodiment 3

[0181]

[0182] Dissolve the raw material acid (1eq) in methanol, add a few drops of concentrated sulfuric acid, and heat to reflux for 8 hours to obtain the ester.

[0183] The above ester (2eq) was heated to 180°C under the protection of nitrogen, and the compound phenyldiazomethane (1eq) was slowly added dropwise at a rate to maintain the reaction temperature at 180°C-190°C. Cooling gave an orange residue. An appropriate amount of 10% ether / n-pentane was added and filtered to obtain a compound with a substituted cyclopropane structure.

[0184]

[0185]

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PUM

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Abstract

The invention provides a compound which is provided with substituted cyclopropane structure represented in the general formula I as follows and a method for preparing the compound and application as hyperglycemic glycogenolytic peptide-1 receptor adjustor for preventing and / or treating metabolic disorder disease (containing but not limited by diabetes, insulin resistance and obesity), cardiovascular disease and nerve degenerative disease (such as Alzheimer's disease) and the like.

Description

technical field [0001] The present invention relates to a class of compounds with a substituted cyclopropane structure, a preparation method and its role as a regulator of glucagon like peptide-1 receptor (GLP-1R) in the prevention and / or treatment of metabolic disorders Medical uses for diseases (including but not limited to diabetes, insulin resistance, obesity, etc.), cardiovascular diseases, neurodegenerative diseases (such as Alzheimer's disease), etc. Background technique [0002] Glucose metabolism disorder, especially diabetes, has become a major disease that seriously threatens human health and life in modern society. It is predicted that diabetes patients in the world are increasing at an annual rate of 6%, and by the end of 2006 there were 320 million patients (60 million people in my country, ranking second). Diabetes mellitus is a group of clinical syndromes caused by the interaction of genetic and environmental factors. It is mainly divided into type 1 and typ...

Claims

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Application Information

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IPC IPC(8): C07C237/38C07C231/14C07D333/40A61K31/195A61K31/381A61P9/00A61P3/00A61P25/28
CPCC07C2101/08C07C237/42C07C2101/02C07C233/54C07D333/40C07C233/63C07C271/28A61P3/00A61P3/04A61P9/00A61P25/00A61P25/16A61P25/28C07C2601/02C07C2601/08
Inventor 王明伟刘青李娜
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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