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pyranobipyridine compounds

A bipyridine and compound technology, applied in the field of pyranobipyridine compounds, can solve the problems of lower central nervous system inhibitory effect, dosage limitation, and lower quality of life of epilepsy patients

Inactive Publication Date: 2021-01-01
EISIA R&D MANAGEMENT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is reported that if the dosage is increased in humans, the central nervous system depressant effect is reduced (Non-Patent Document 9); quality of life in epilepsy patients on long-term use, and leads to dosage restrictions

Method used

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Examples

Experimental program
Comparison scheme
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example

[0245] Compounds (I) to (XXII) of the present invention can be produced, for example, by the methods described in the following examples, and the effects of the compounds can be confirmed by the methods described in the following test examples. It should be noted, however, that these examples are illustrative, and the present invention is in no way limited to the following specific examples, and furthermore, these examples can be modified without departing from the scope of the present invention.

[0246] The compound described with the name of a document etc. shows that it was manufactured based on the said document etc.

[0247] The abbreviations used in this specification are commonly used abbreviations known to those skilled in the art. In this specification, the following abbreviations are used.

[0248] AIBN: 2,2'-Azobis(isobutyronitrile)

[0249] (Ataphos) 2 PdCl 2 : Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)palladium(II) dichloride

[0250]DCM: dichloromet...

example 1

[0280] Synthesis of 6H-pyrano[3,2-b:5,4-b']dipyridin-8(7H)-one

[0281] [chemical formula 56]

[0282]

[0283] (1) Synthesis of (3-bromo-6-methoxypyridin-2-yl)methyl acetate

[0284] 3-Bromo-6-methoxy-2-methylpyridine (CAS No. 126717-59-7) (4.87kg, 24.1mol, 1 equivalent) was dissolved in chloroform (25L) and cooled to 0-10 ℃. To this solution was added 65% mCPBA (8.32 kg, 31.3 mol, 1.3 eq) and the resulting suspension was heated at 40°C to 50°C for 10 hours. The reaction solution was cooled to 10°C and stirred for 15 minutes. This suspension was filtered, and the residue was washed with chloroform (20 L). The combined filtrates were dried over anhydrous sodium sulfate and filtered. To the obtained filtrate was added acetic anhydride (12.2 L, 129 mol, 5.4 equivalents) at room temperature, and heated and stirred at 65°C to 70°C for 12 hours. After the reaction, the reaction solution was cooled to room temperature. Methanol (35 L) was added to the reaction liquid, ...

example 2

[0295] Synthesis of 9-bromo-7-(pyridin-3-yl)-6H-pyrano[3,2-b:5,4-b']dipyridin-8(7H)-one

[0296] [chemical formula 57]

[0297]

[0298] (1) Synthesis of 7-(pyridin-3-yl)-6H-pyrano[3,2-b:5,4-b']dipyridin-8(7H)-one

[0299] To 6H-pyrano[3,2-b:5,4-b']dipyridin-8(7H)-one (4g, 20.0mmol, 1 equivalent) obtained in Production Example 1, silver carbonate (6.61 g, 24.0mmol, 1.2 equivalents), copper iodide (I) (2.28g, 12.0mmol, 0.6 equivalents), pyridine (9.7mL, 120mmol, 6 equivalents) and DMF (100mL) in a mixture under an oxygen environment at 65 A suspension of 1,3-propanediol pyridine-3-boronate (CAS No. 131534-65-1 ) (9.77 g, 59.9 mmol, 3 equiv) in DMF (100 mL) was added slowly at °C. The reaction mixture was stirred overnight at 65 °C. The reaction solution was cooled to room temperature, and NH silica gel was added. diatomaceous earth TM Filter and wash the residue with chloroform. The obtained filtrate was concentrated under reduced pressure. The obtained residue wa...

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Abstract

Compounds represented by formulas (I) to (XXII) or pharmaceutically acceptable salts thereof are disclosed.

Description

technical field [0001] The present invention relates to a pyranobipyridine compound with α-amino-3-hydroxyl-5-methyl-4-isoxazole propionic acid (AMPA) receptor inhibitory effect and a pharmaceutically acceptable salt thereof. Background technique [0002] Glutamate released from the presynapse is known to play an important role in excitatory signaling in the central nervous system. This effect is produced by binding to glutamate receptors present in the postsynapse, and these glutamate receptors are divided into ion channel receptors and G protein-coupled receptors, the former are further divided into α-amino - 3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor, N-methyl-D-aspartic acid (NMDA) receptor, kainate receptor, etc. Among them, AMPA receptor is a receptor widely expressed in the brain, and plays a major role in the regulation of fast excitatory synaptic transmission or synaptic plasticity. [0003] AMPA receptors are thus known to play an important role...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/147A61P25/30A61K31/4375A61K31/444A61K31/497A61K31/506A61P9/10A61P21/02A61P25/00A61P25/04A61P25/08A61P25/14A61P25/16A61P25/18A61P25/22A61P25/24A61P25/28
CPCC07D491/052C07D491/147A61P21/02A61P25/00A61P25/02A61P25/04A61P25/08A61P25/14A61P25/16A61P25/18A61P25/22A61P25/24A61P25/28A61P25/30A61P43/00A61P9/10C07C201/00A61K31/436A61K31/4375A61K31/444A61K31/497A61K31/506
Inventor 黑川利树吉田融慎光玉小林义久福元浩德武田邦稔大桥芳章小竹真涩口朋之渡边亨北阳一广田信介福山尚镰田恭明
Owner EISIA R&D MANAGEMENT CO LTD
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