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Heterocyclic compounds for the treatment of epilepsy

A compound and heterocyclic technology, applied in the field of heterocyclic compounds and their salts, can solve the problems of epilepsy, motor dysfunction, disturbing the balance of neuronal activity, etc., and achieve the effect of wide therapeutic spectrum and few side effects

Pending Publication Date: 2021-07-23
OTSUKA PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

About 70% of these patients can control their seizures with existing antiepileptic drugs and continue their daily life without problems, but the remaining 30% of people with epilepsy cannot adequately control their seizures and are concerned that the seizures may be in the Happened without warning
Most existing antiepileptic drugs aim to normalize the excitatory / inhibitory imbalance of neural activity by inhibiting the hyperexcitability and hypersynchrony of neuronal activity, but doses higher than the optimal dose may disturb the balance of neuronal activity and Induces motor dysfunction and seizures

Method used

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  • Heterocyclic compounds for the treatment of epilepsy
  • Heterocyclic compounds for the treatment of epilepsy
  • Heterocyclic compounds for the treatment of epilepsy

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0396] Hereinafter, the present invention is further described in detail by the following test examples, reference examples and examples, but they do not limit the present invention, and they can be changed to the extent that they do not depart from the scope of the present invention.

[0397] The following abbreviations are used in this specification.

[0398]

[0399]

[0400]

[0401]

[0402] In the examples below, "room temperature" generally indicates about 10°C to about 35°C. Ratios indicated for mixed solvents are by volume unless otherwise indicated. Percentages indicate % by weight unless otherwise indicated.

[0403] 1 HNMR (proton nuclear magnetic resonance spectrum) was measured by Fourier transform type NMR (either of Bruker AVANCE III 400 (400 MHz) and Bruker AVANCE III HD (500 MHz)). In silica gel column chromatography, when expressed as basic, aminopropylsilane-bonded silica gel is used.

[0404] The absolute configuration of the compound was a...

Embodiment 1

[0527] Synthesis of 3-methoxy-6-(2-phenoxypyrimidin-5-yl)pyridazine

[0528] Containing 2-phenoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (5.00g), 3-chloro -6-methoxypyridazine (3.64g), PdCl 2 (dppf)DCM (0.137g), K 3 PO 4 (7.12g), 1,4-di A mixture of alkanes (50 mL) and water (25 mL) was heated to reflux for 2 hours under nitrogen atmosphere. The reaction solution was poured into water, and the product was extracted with AcOEt. The organic layer was washed with water and brine and dried over anhydrous sodium sulfate, then concentrated. The residue was purified by silica gel column chromatography (DCM / AcOEt) to obtain the title compound (4.42 g).

Embodiment 4

[0530] Synthesis of 3-(2-(3-fluorophenoxy)pyrimidin-5-yl)-6-methoxypyridazine

[0531] Will contain 5-bromo-2-(3-fluorophenoxy)pyrimidine (2.234g), (BPin) 2 (2.63g), PdCl 2 (dppf)DCM (0.282g), AcOK (1.358g) and 1,4-di The mixture of alkanes (20 mL) was heated to reflux for 2 hours under a nitrogen atmosphere. To the reaction solution was added 3-chloro-6-methoxypyridazine (1.00 g), PdCl 2 (dppf)DCM (0.282g), K 3 PO 4 (2.94 g) and water (5 mL), and the mixture was heated to reflux overnight under an atmosphere of nitrogen. Water and AcOEt were added to the reaction solution, the mixture was filtered through celite, and the product was extracted with AcOEt. The organic layer was washed with water and brine and dried over anhydrous sodium sulfate, then concentrated. The precipitated crystals were washed with EtOH, so as to obtain the target compound (947 mg).

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Abstract

The present invention provides a novel heterocyclic compound represented by Formula [I] and a salt thereof: wherein the symbols are as defined in the specification, which is useful for treating, preventing and / or diagnosing seizure and the like in disease involving epileptic seizure or convulsive seizure (including multiple drug resistant seizure, refractory seizure, acute symptomatic seizure, febrile seizure and status epilepticus), as well as a medical use therefor.

Description

technical field [0001] The present invention relates to a heterocyclic compound and its salt. The present invention also relates to a medicament which contains a heterocyclic compound or a salt thereof as an active ingredient and is useful for treating, preventing and / or diagnosing seizures and the like in diseases involving epileptic seizures or convulsive seizures. Background technique [0002] The prevalence of epilepsy is about 1% of the population. It is considered a common neurological disorder with about 1 million patients in Japan, a lifetime incidence of 3% to 4%, and it is estimated that tens of thousands of people suffer from epilepsy every year. About 70% of these patients can control their seizures with existing antiepileptic drugs and continue their daily life without problems, but the remaining 30% of people with epilepsy cannot adequately control their seizures and are concerned that the seizures may be in the Occurs without warning. Most existing antiepil...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/34C07D239/54C07D401/04C07D403/04C07D405/04C07D413/04C07D417/04C07D471/04C07D487/04A61P25/08A61K31/506
CPCC07D403/04C07D401/04C07D471/04C07D487/04C07D405/04C07D413/04C07D239/34C07D417/04C07D239/54A61P25/08A61K31/506A61K31/513C07D239/22C07D239/47C07D401/12
Inventor 筱原友一岩田伸铃木征希新井健太伊藤展明千叶拓也
Owner OTSUKA PHARM CO LTD
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