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Pyridazinone derivative

A compound and optional technology, applied in the directions of drug combinations, active ingredients of heterocyclic compounds, muscular system diseases, etc., can solve the problems of prolonging the PR interval of electrocardiogram and QRS width, etc.

Pending Publication Date: 2021-04-16
SUMITOMO DAINIPPON PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is also known that antiarrhythmic drugs with inhibition of Nav1.5 prolong the PR interval and QRS width in the ECG

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0925] N-(4-cyanophenyl)-2-[3-(4-methylpiperidin-1-yl)-6-oxopyridazin-1(6H)-yl]acetamide

[0926]

Embodiment 2

[0930]N-(4-cyanophenyl)-2-[3-(4,4-dimethylpiperidin-1-yl)-6-oxopyridazin-1(6H)-yl]acetamide

[0931]

[0932] The compound of Reference Example 3 (60 mg), 4,4-dimethylpiperidine hydrochloride (93 mg) and diisopropylethylamine (1 mL) were dissolved in dimethylacetamide (0.5 mL) The solution was stirred at 150 °C for 11 h. After the reaction was completed, water was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by reverse phase HPLC (eluent; 0.035% trifluoroacetic acid in acetonitrile / water) and then by amino silica gel column chromatography (solvent; chloroform:methanol=99:1, then 93: 7) Purification to give the title compound (22 mg).

[0933] 1 H-NMR (400 MHz, CDCl 3 ) δ : 9.78 (s, 1H), 7.65 (d, J = 8.5 Hz, 2H),7.57 (d, J = 8.5 Hz, 2H), 7.25 (d, J = 9.8 Hz, 1H), 6.94 (d, J = 10.4 Hz,1H), 4.84 (s, 2H), 3.32-3.28 (m, ...

Embodiment 3-36

[0935] According to the method of Example 1 or 2 and common reaction conditions, the compounds of Examples 3-36 were obtained using the corresponding material compounds.

[0936]

[0937]

[0938]

[0939]

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PUM

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Abstract

Provided are: a pyridazinone derivative and / or a pharmaceutically acceptable salt thereof, which is useful as a therapeutic agent and / or a prophylactic agent for diseases in which Nav1.1 is involved and various central nervous system diseases; and a medicine containing the pyridazinone derivative and / or the pharmaceutically acceptable salt thereof as an active ingredient. A compound represented by formula (1) or a pharmaceutically acceptable salt thereof. [In the formula, M1 represents a saturated or partially unsaturated C4-12 carbocyclic group or the like; R1 and R2 independently represent a hydrogen atom or the like; M2 represents a group represented by formula (2a) or the like; X1a, X1b and X1c independently represent N or the like; X2, X3 and X4 independently represent CR3 or the like; A1 and A2 independently represent N or the like; and R3 represents a hydrogen atom or the like.].

Description

technical field [0001] The present invention relates to pyridazinone derivatives or pharmaceutically acceptable salts thereof useful as drugs for the treatment and / or prevention of diseases involving sodium channels (particularly Nav1.1) and various central nervous system diseases, and compounds comprising them Drugs as active ingredients. Background technique [0002] Nav1.1 is one of the voltage-gated sodium channels (VGSCs), and is expressed, for example, in palvalbmin-positive GABA neurons (PV-GABA neurons). Nav1.1 is known to be important for the function of neuronal firing in neurons. [0003] It has been suggested that patients suffering from central nervous system disorders such as schizophrenia, autism spectrum disorder (ASD) and attention deficit hyperactivity disorder (ADHD) have dysfunction in Nav1.1 expressing GABA-ergic neurons (non Patent Documents 1 and 2). [0004] It has also been reported that heterozygous loss-of-function mutations in the SCN1A gene ca...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D237/14A61K31/501A61K31/506A61K31/5377A61K31/538A61K31/55A61K31/551A61P21/02A61P25/08A61P25/16A61P25/18A61P25/24A61P25/28A61P43/00C07D237/22C07D401/04C07D401/14C07D403/04C07D403/14C07D405/14C07D417/14C07D471/04C07D487/04C07D487/10C07D491/048C07D491/08
CPCA61K31/501A61K31/506A61K31/5377A61K31/538A61K31/55A61K31/551A61P21/02A61P25/08A61P25/24A61P25/28A61P25/16A61P25/18A61P43/00C07D237/22C07D237/14C07D403/14C07D401/04C07D401/14C07D403/04C07D405/14C07D417/14C07D471/04C07D487/10C07D487/04C07D491/048A61P25/00C07D401/12C07D403/06C07D403/12C07D413/12C07D405/04C07D409/14C07D491/107C07D405/12C07D417/12C07D413/14C07D513/04C07D498/08C07D519/00C07D451/02A61K45/06A61K31/541A61K2300/00A61K31/517A61K31/519A61K31/5386C07D471/08
Inventor 西田友明上町昊岩田昌门柴田一西卷拓也清重沙织
Owner SUMITOMO DAINIPPON PHARMA CO LTD
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