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3,4-dihydro-iii 2 benzopyran-1 ketone kind compound, its preparation method and use

A technology of benzopyran, -1H-2-, applied in 3 fields

Inactive Publication Date: 2007-02-14
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] So far, the LAR and PTPσ inhibitors reported in the literature are all vanadic acid-based inorganic compounds or peptide compounds, which have encountered problems in the strength of action, selectivity and drug-likeness. These undoubtedly provide us with a new small molecule non-peptide Organoids offer opportunities as their inhibitors

Method used

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  • 3,4-dihydro-iii 2 benzopyran-1 ketone kind compound, its preparation method and use
  • 3,4-dihydro-iii 2 benzopyran-1 ketone kind compound, its preparation method and use
  • 3,4-dihydro-iii 2 benzopyran-1 ketone kind compound, its preparation method and use

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Embodiment

[0045] In all embodiments, the melting point is measured with the SWG X-4 micro melting point instrument of Shanghai Precision Scientific Instrument Co., Ltd., and the thermometer is not corrected; 1H-NMR is recorded with a Varian Mercury 300 nuclear magnetic resonance instrument, and the chemical shift is expressed in δ (ppm). The silica gel not specified is 200-300 mesh.

[0046] I. Below we prepare compound 3-hydroxyl-5 formyl-6-methoxy-1H-2-benzopyran-1-ketone (structural formula 14) and 3-hydroxyl-5 formyl-6-hydroxyl- 1H-2-benzopyran-1-one (structural formula 15) is a specific example to further illustrate the first preparation method above, but does not limit this patent in any way.

[0047]

[0048] 1. Synthesis of Compound 2

[0049] Weigh 33g of malonic acid, dissolve it with 75ml of pyridine, add 19ml of m-methoxybenzaldehyde, and 1.5ml of piperidine. The resulting mixture was reacted with stirring at 100°C for 3h, then at 130°C for 10min. Cool to room temperat...

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Abstract

The present invention relates to one kind of 3, 4-dihydro-1H-2-benzopyran-1-ketone compounds, and provides the preparation process of these compounds. These compounds have LAR and PTPsigma inhibiting effect, and may be used in treating various types of diabetes, obesity and their complication as well as other diseases caused by excessive activity or over expression of PTP-LAR and / or PTPsigma, such as tumor and nervous degenerative disease.

Description

technical field [0001] The present invention relates to the synthesis and use of a class of organic compounds, more specifically to the preparation method and use of a class of 3,4-dihydro-1H-2-benzopyran-1-one compounds. Such compounds can be used as leukocyte common antigen-related protein (LAR) and protein tyrosine phosphatase σ (PTPσ) inhibitors, can be used for the treatment of various diabetes, obesity and its complications, and can also be used for the treatment of LAR and / or Other diseases caused by excessive PTPσ activity or expression, such as tumors and neurodegenerative diseases. Background technique [0002] Because the HLA-D gene on the short arm of the sixth pair of chromosomes determines the genetic susceptibility of patients with type I diabetes, they respond abnormally to environmental factors, especially viral infections or chemical toxic substances, directly or indirectly through autoimmune reactions, causing pancreatic islet Beta cells are destroyed, re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/76C07D311/78C07D493/04A61K31/366A61P5/50A61P3/04A61P3/10
Inventor 李欣李佳周越洋凌青沈竞康李静雅张薇
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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