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Pyrazole derivative

A technology of pyrazole derivatives and triazolyl, which is applied in the field of pyrazole derivatives and can solve the problems of undisclosed OX receptor antagonism

Inactive Publication Date: 2013-12-11
TAISHO PHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, Patent Document 2 does not disclose OX receptor antagonism or the compounds described in this application

Method used

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Examples

Experimental program
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Effect test

Embodiment

[0216] Hereinafter, the present invention will be described in more detail with reference to Reference Examples, Examples, and Test Examples. However, these examples are not intended to limit the invention. Furthermore, modifications or variations may be made to the present invention without departing from the scope of the present invention.

[0217] In the following Reference Examples and Examples, the microwave reactor used was an Initiator from Biotage Japan Ltd.

[0218] In the following Reference Examples and Examples, SNAPCartridgeKP-Sil from Biotage Japan Ltd. was used as "KP-Sil" for purification using column chromatography; SNAPCartridgeHP-Sil from Biotage Japan Ltd. was used as "HP-Sil" and SNAPCartridge KP-NH from Biotage Japan Ltd. was used as "KP-NH".

[0219] In the following Reference Examples and Examples, purification by preparative high performance liquid chromatography (HPLC) was performed under the conditions shown below. However, in the case of a compou...

Embodiment 2

[0249] Referring to Example 25-fluoro-2-(1H-pyrazol-5-yl)pyridine hydrochloride

[0250] [Formula 13]

[0251]

[0252] 4mol / L HCl-EtOAc solution (5 mL) was added to a solution of the compound (0.84 g, 3.4 mmol) obtained in Reference Example 1 in MeOH (10 mL), and the mixture was stirred at room temperature for 16 hours and heated at 60° C. Stir for 3 hours. After standing to cool at room temperature, the solvent in the reaction mixture was distilled off under reduced pressure. The obtained residue was dissolved in Et 2 O for 1 hour. Then, the deposited solid was collected by filtration and dried by heating under reduced pressure to obtain the title compound (0.62 g) (colorless powder).

[0253] MS (ESI positive ion) m / z: 164[M+H]+, 186[M+Na]+

[0254] Referring to Example 3 {2-[3-(5-fluoropyridin-2-yl)-1H-pyrazol-1-yl]ethyl}carbamate tert-butyl ester

[0255] [Formula 14]

[0256]

[0257] N-(2-bromoethyl) tert-butyl carbamate (1.9g, 8.5mmol) and Cs 2 CO 3 (6.4...

Embodiment 4

[0259] Referring to Example 42-[3-(5-fluoropyridin-2-yl)-1H-pyrazol-1-yl]ethylamine dihydrochloride

[0260] [Formula 15]

[0261]

[0262] 4mol / L HCl-EtOAc solution (5mL) was added to the compound obtained in reference example 3 (1.3g, 4.2mmol) in CHCl 3 (20 mL), and the mixture was stirred at room temperature for 24 hours. The solvent in the reaction mixture was distilled off under reduced pressure, and the obtained residue was dissolved in Et 2 O for 1 hour. Then, the deposited solid was collected by filtration and dried by heating under reduced pressure to obtain the title compound (0.86 g) (colorless powder).

[0263] MS (ESI positive ion) m / z:207[M+H]+

[0264] Referring to Example 55-fluoro-2-(1H-pyrazol-4-yl)pyridine

[0265] [Formula 16]

[0266]

[0267] 2mol / LNa 2 CO 3 Aqueous solution (8.5mL, 17.1mmol) and Pd(PPh 3 ) 4 (0.20g, 0.17mmol) was added to 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate A solution of tert-butyl e...

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PUM

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Abstract

A compound represented by formula (IA) or a pharmaceutically acceptable salt thereof, which is useful for the treatment or prevention of diseases such as sleep disorder, depression, anxiety disorders, panic disorder, schizophrenia, drug dependence, Alzheimer's disease, Parkinson's disease, Huntington's chorea, eating disorder, pain, digestive diseases, epilepsy, inflammations, immunity-related diseases, incretion-related diseases and hypertension, and of which the action relies on an orexin (OX) receptor antagonistic activity.

Description

technical field [0001] The present invention relates to a compound having an orexin (OX) receptor antagonistic action and a pharmaceutically acceptable salt thereof, and a therapeutic or preventive agent comprising the same as an active ingredient for diseases such as sleep disorders, depression, anxiety, Panic disorder, schizophrenia, drug dependence, Alzheimer's disease, Parkinson's disease, Huntington's disease, eating disorders, pain, gastrointestinal disorders, epilepsy, inflammation, immune-related disorders, endocrine-related disorders, and hypertension . Background technique [0002] Orexin is a neuropeptide cleaved from preproorexin and expressed specifically in the lateral hypothalamus. So far, OX-A consisting of 33 amino acids and OX-B consisting of 28 amino acids have been identified. All of these molecules play important roles in regulating wakefulness patterns and regulating feeding. [0003] Both OX-A and OX-B act on OX receptors. So far, OX receptors have...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14A61K31/4192A61K31/4439A61K31/444A61K31/506A61P1/00A61P1/14A61P5/00A61P9/12A61P25/04A61P25/08A61P25/14A61P25/16A61P25/18A61P25/20A61P25/22A61P25/24A61P25/28A61P25/30A61P29/00A61P29/02A61P37/02A61P43/00C07D403/12C07D405/14
CPCA61P1/00A61P1/14A61P5/00A61P9/12A61P25/00A61P25/04A61P25/08A61P25/14A61P25/16A61P25/18A61P25/20A61P25/22A61P25/24A61P25/28A61P25/30A61P29/00A61P29/02A61P37/02A61P43/00C07D401/14C07D403/12C07D405/14A61K31/506A61K31/4192A61K31/4439
Inventor 野泽大铃木亮二村彩下野梨绘阿部正人太田裕之荒木裕子
Owner TAISHO PHARMACEUTICAL CO LTD
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