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4,4-difluoro-1,2,3,4-tetrahydro-5h-1-benzoazepine derivative or salt of the same

A technology of benzazepines, compounds, applied in the field of medicine using said compounds as active ingredients

Inactive Publication Date: 2006-05-31
ASTELLAS PHARMA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] However, these patent documents have no description on the 4,4-difluoro-1,2,3,4-tetrahydro-5H-1-benzazepine derivatives of the present invention

Method used

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  • 4,4-difluoro-1,2,3,4-tetrahydro-5h-1-benzoazepine derivative or salt of the same
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  • 4,4-difluoro-1,2,3,4-tetrahydro-5h-1-benzoazepine derivative or salt of the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0331] 150 mg of the compound of Reference Example 20 was dissolved in 5 ml of DMF, mixed with 43 mg of HOBt, 61 mg of WSCD, 35 mg of glycinamide hydrochloride and 0.045 ml of triethylamine, followed by stirring at room temperature for 4 hours. To the reaction mixture were added saturated aqueous sodium bicarbonate solution and EtOAc, and the layers were separated. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated and the obtained residue was recrystallized from EtOH to give 139 mg of (2Z)-N-(2-amino-2-oxoethyl)-2-{1-[4-(benzyloxy)-2- (Trifluoromethyl)benzoyl]-4,4-difluoro-1,2,3,4-tetrahydro-5H-1-benzazepine-5-ylidene}acetamide.

[0332] In the same manner as in Example 1, using the corresponding raw materials, respectively, Examples 2 to 16 shown in Table 10 were prepared.

Embodiment 17

[0334] 150 mg of the compound of Example 20 was dissolved in 3.5 ml of THF, mixed with 0.3 ml of thionyl chloride and 2-3 drops of DMF, and stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure, and thionyl chloride was further removed by azeotropic distillation using toluene. The obtained residue was dissolved in THF, and the solution was added dropwise to ammonia water. EtOAc was added to the reaction mixture, and the layers were separated. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The obtained crude product was recrystallized in iPrOH-diisopropyl ether mixed solvent to obtain 126 mg of (2Z)-2-{1-[4-(benzyloxy)-2-(trifluoromethyl)benzoyl]- 4,4-Difluoro-1,2,3,4-tetrahydro-5H-1-benzazepine-5-ylidene}acetamide.

[0335] In the same manner as in Example 17, using the corresponding starting materials, Example 18 shown in Table 11 was prepared. In addition, in the same manner as in Referen...

Embodiment 21

[0337] 325 mg of the compound of Example 6 was dissolved in 5 ml of 1,2-dichloroethane, mixed with 148 mg of m-chlorobenzoic acid under ice-cooling, and stirred at room temperature for 4 hours. The reaction mixture was mixed with 10% (w / v) Na 2 S 2 O 3 ·5H 2O aqueous solution, water and chloroform were mixed, and the layers were separated. The organic layer was washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, and the solvent was evaporated. The obtained crude product was subjected to silica gel column chromatography, eluted with chloroform-MeOH (23:2), and concentrated under reduced pressure to obtain 121 mg ( 2Z)-N-(2-amino-2-oxoethyl)-2-{4,4-difluoro-1-[4-(propylsulfinyl)benzoyl]-1,2,3 , 4-tetrahydro-5H-1-benzazepine-5-ylidene}acetamide.

[0338] Example 22 shown in Table 10 was prepared in the same manner as Example 21 using the corresponding starting materials. In addition, using the methods described above or the method...

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Abstract

The present invention provides a novel 4,4-difluoro-1,2,3,4-tetrahydro-5H-1-benzazepine derivative or a pharmaceutically acceptable salt thereof, which can be used as a therapeutic Or an agent for the prevention of nocturnal frequency and / or diabetes insipidus.

Description

technical field [0001] The present invention relates to a medicament, specifically a novel 4,4-difluoro-1,2,3,4-tetrahydro-5H-1-benzazepine derivative or a salt thereof, which can be used for treatment A therapeutic agent for central diabetes insipidus or a medicament for nocturnal urinary frequency, and also a medicament using the compound as an active ingredient. technical background [0002] Arginine vasopressin (AVP) is a 9-amino acid peptide biosynthesized and secreted by the hypothalamic-pituitary system. The receptors for AVP can be divided into V 1a , V 1b and V 2 Three subtypes, the main pharmacological effect of AVP on the peripheral system is known to be via V 1a Receptor-mediated vasoconstriction and via V 2 Receptor-mediated antidiuretic effect. as V 2 A receptor selective agonist, desmopressin was synthesized as a peptide (a peptide in which the amino group of cysteine ​​at position 1 of AVP was removed and the arginine at position 8 was changed to d-for...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D223/16A61K31/55A61P13/02A61P43/00C07D401/06C07D401/12C07D403/06C07D403/12C07D417/06
Inventor 古盐裕之塚本一成掛札昭夫赤松清二郎斋藤亲
Owner ASTELLAS PHARMA INC
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