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Benzazepine compound

A kind of technology of hetero compound and benzazepine, applied in the field of benzazepine hetero compound, can solve the problems such as undisclosed deuterium compound

Inactive Publication Date: 2015-03-25
OTSUKA PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] However, Patent Document 3 does not disclose the deuterated compound of the present invention at all

Method used

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Examples

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Effect test

reference example 1

[0062] N-(4-(7-chloro-5-oxyl-2,3,4-trihydro-1H-benzo[b]azepine -1-carbonyl)-3-methylphenyl)-2-methylbenzamide preparation

[0063] To N-(4-(7-chloro-5-hydroxyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine - Manganese dioxide (2 g) was added to a suspension of 1-carbonyl)-3-methylphenyl)-2-methylbenzamide (2 g) in dichloromethane (40 mL), and refluxed for 7 hours. After cooling the reaction mixture, it was filtered through celite, washed with dichloromethane, and purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1→3:1) to obtain 0.94 g of the title compound. Properties: colorless amorphous powder

[0064] 1 H-NMR (CDCl 3 )δppm

[0065] 1.91-1.31(2H, m), 2.43(3H, s), 2.49(3H, s), 2.89(2H, t, J=6.3Hz), 3.30-4.60(2H, m), 6.48-7.00(2H, m), 7.01-7.70 (8H, m), 7.78 (1H, s).

Embodiment 1

[0067] N-(4-(7-chloro-5-hydroxy-2,3,4-trihydro-5-deutero-1H-benzo[b]azepine -1-carbonyl)-3-methylphenyl)-2-methylbenzamide preparation

[0068] At 0°C, N-(4-(7-chloro-5-oxyl-2,3,4-trihydro-1H-benzo[b]azepine -1-carbonyl)-3-methylphenyl)-2-methylbenzamide (0.4g) in deuterated methanol (10mL) solution was added sodium borodeuteride (Sodium borodeuteride) (0.045g), in the same Stir at temperature for 2 hours. Heavy water (2 mL) was added to the resulting reaction mixture, and after stirring for 10 minutes, water was added and extracted with ethyl acetate. The resulting aqueous layer was extracted again with ethyl acetate. The resulting ethyl acetate layers were combined, dried over anhydrous magnesium sulfate, and the solvent was distilled off, and the residue was recrystallized from acetone-diethyl ether to obtain 0.35 g of the title compound.

[0069] Yield: 87%

[0070] Appearance: white powder

[0071] 1 H-NMR (DMSO-d6, 80°C) δppm

[0072] 1.40-2.19(4H, m), 2.36(3H,...

Embodiment 2

[0076]

[0077] N-(4-(7-chloro-2,3-dihydro-5-hydroxy-4,4,5-trideutero-1H-benzo[b]azepine -1-carbonyl)-3-methylphenyl)-2-methylbenzamide preparation

[0078] To N-(4-(7-chloro-5-oxyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine -1-carbonyl)-3-methylphenyl)-2-methylbenzamide (300mg) in deuterated methanol (10mL) solution was added 0.05M sodium hydroxide deuterated methanol solution (13μl), under argon atmosphere Stir at room temperature. After stirring for 16 hours, use 1 H-NMR confirmed that the 4-position proton disappeared, and sodium borodeuteride (0.037 g) was added to the reaction liquid at 0°C, and stirred at the same temperature for 2 hours. Heavy water (2 mL) was added to the resulting reaction mixture, and after stirring for 10 minutes, water was added and extracted with ethyl acetate. The resulting aqueous layer was extracted again with ethyl acetate. The resulting ethyl acetate layers were combined, dried over anhydrous magnesium sulfate, and the solvent was distill...

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Abstract

An object of the present invention is to provide a novel benzazepine compound or a salt thereof, which has excellent vasopressin antagonistic activity. The benzazepine compound or a salt thereof of the present invention is represented by Formula (1): wherein R 1 , R 2 and R 5 may be the same or different and each represents H or D; and R 3 and R 4 each represents a C 1-6 alkyl group, a C 1-6 deuteroalkyl group, or a C 1-6 perdeuteroalkyl group.

Description

[0001] The application date is October 25, 2010, the application number is 201080048410.3 (the international application number is PCT / JP2010 / 068807), the invention name is "benzazepine A divisional application of the application of "Compound". technical field [0002] The present invention relates to benzazepine (benzazepine) compound. Background technique [0003] So far, several compounds having vasopressin antagonistic activity have been developed (for example, Patent Documents 1 to 3 and Non-Patent Documents 1 to 2), but it is desired to develop compounds with more excellent vasopressin antagonistic activity. active compound. [0004] Example 430 of Patent Document 3 discloses a compound having an excellent vasopressin antagonistic activity, and among them, Tolvaptan represented by the following formula is also disclosed. [0005] [0006] However, Patent Document 3 does not disclose the deuterated compound of the present invention at all. [0007] Patent Docum...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D223/16A61K31/55A61P9/12A61P9/04A61P13/12A61P1/16A61P3/10A61P3/12A61P9/10A61P7/10A61P7/02
CPCC07D223/16A61K31/55A61K45/06A61P1/08A61P1/16A61P13/12A61P3/00A61P3/12A61P7/02A61P7/10A61P9/00A61P9/04A61P9/10A61P9/12A61P3/10A61K2300/00
Inventor 菅庆三大谷直明
Owner OTSUKA PHARM CO LTD
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