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Pharmaceutical composition for treatment or prevention of ophthalmic diseases

A technology for compositions and medicines, applied in the directions of medicine combinations, active ingredients of heterocyclic compounds, sensory diseases, etc., can solve problems such as ketone compounds that are not specifically disclosed

Inactive Publication Date: 2012-04-25
UBE IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] Furthermore, none of the above-mentioned documents specifically discloses the presence of benzazepines related to the compounds of the present invention A benzazepine with a fused imidazole ring structure on the side chain of the ring Ketones

Method used

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  • Pharmaceutical composition for treatment or prevention of ophthalmic diseases
  • Pharmaceutical composition for treatment or prevention of ophthalmic diseases
  • Pharmaceutical composition for treatment or prevention of ophthalmic diseases

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0396] 3-Oxo-8-[2-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrimidin-2-yl)ethoxy]-2-(2,2,2- Trifluoroethyl)-2,3,4,5-tetrahydro-1H-2-benzazepine -4-Ethyl acetate hydrochloride

[0397] 1-(a)1-Bromo-4-hydroxy-2-butanone

[0398] To a solution of 169 g (1.92 mol) of 4-hydroxy-2-butanone in 1.9 L of methanol was added dropwise 300 g (1.88 mol) of bromine at -5°C over 30 minutes. After the dropwise addition, the temperature was slowly raised to room temperature, and stirred for 2 hours. Next, 3.84 L (3.84 mol) of 2N sulfuric acid was added at 0°C, stirred at 10°C for 3.5 hours, and further stirred at room temperature for 22 hours.

[0399] After completion of the reaction, 325 g of sodium chloride was added to the reaction solution, followed by extraction with 5.4 L of a mixed solution of chloroform:methanol=2:1 (V / V). Furthermore, the aqueous layer was extracted four times with 1.7 L of a mixed solution of chloroform:methanol=9:1 (V / V). The combined organic layers were washed with s...

Embodiment 2

[0418] 3-Oxo-8-[2-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrimidin-2-yl)ethoxy]-2-(2,2,2- Trifluoroethyl)-2,3,4,5-tetrahydro-1H-2-benzazepine -4-Acetic acid trifluoroacetate

[0419] The 3-oxo-8-[2-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrimidin-2-yl)ethoxy obtained in Example 1-(d) ]-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydro-1H-2-benzazepine - 0.054 g (0.10 mmol) of 4-ethyl acetate hydrochloride was dissolved in 2 mL of methanol: tetrahydrofuran = 1: 1 mixed solution, and 0.2 mL of water and 0.3 mL of 1 equivalent of aqueous sodium hydroxide solution were added under ice-cooling. Stir for 2 hours.

[0420] After the reaction, 0.025 mL of acetic acid was added to the reaction solution, and concentrated under reduced pressure. The obtained residue was subjected to solid-phase extraction (cartridge: Sep-Pak C18 (5 g / 20 mL (manufactured by Waters), elution solvent: 0.05% trifluoroacetic acid aqueous solution → acetonitrile: 0.05% trifluoroacetic acid aqueous solution = 3: 7 (V / V)) ...

Embodiment 3

[0424] 3-Oxo-8-[2-(1,2,3,4-tetrahydroimidazo[1,2-b][1,2,4]triazin-6-yl)ethoxy]-2 -(2,2,2-Trifluoroethyl)-2,3,4,5-tetrahydro-1H-2-benzazepine -4-Acetic acid trifluoroacetate

[0425] 3-(a) 2-(imidazo[1,2-b][1,2,4]triazin-6-yl)ethanol

[0426] To a solution of 1.92 g (20.0 mmol) of 3-amino-1,2,4-triazine in 40 mL of ethanol, 3.67 g of 1-bromo-4-hydroxyl-2-butanone obtained in Example 1-(a) was added g (22.0mmol), heated to reflux for 2 hours.

[0427] After completion of the reaction, the reaction solution was concentrated under reduced pressure, 200 mL of a mixed solution of chloroform:methanol=9:1 (V / V) was added to the obtained residue, and insoluble matter was removed by filtration. The filtrate was washed successively with water and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (elution solvent: chloroform:methanol=30:1→9:1...

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Abstract

A pharmaceutical composition for treating or preventing diseases associated with vascularization in eyes, which comprises a benzazepinone compound represented by structural formula (I) [wherein R1 represents a C1-C6 alkyl group, or a halogeno-C1-C6 alkyl group; R2 represents a carboxy group which may be protected; and Y represents a group represented by general formula (II) (wherein Z represents CH or a nitrogen atom)] or a pharmacologically acceptable salt thereof as an active ingredient.

Description

technical field [0001] The present invention relates to novel benzazepines that can be used as drugs A pharmaceutical composition comprising a ketone (Benzazepinone, benzazepinone) compound and a pharmaceutically acceptable salt thereof as an active ingredient. In more detail, the benzazepines described in the present invention Keto compounds are antagonists of αv integrin receptors (in particular, αvβ3 and αvβ5), and therefore, can be used as therapeutic agents against diseases associated with αv integrin receptors, such as intraocular angiogenic diseases and / or prophylactics. Background technique [0002] Intraocular vascular diseases such as diabetic retinopathy, retinopathy of prematurity, and age-related macular degeneration (hereinafter abbreviated as AMD) are pathological conditions that often cause problems in clinical ophthalmology, causing severe reduction in vision. In particular, AMD is a major cause of blindness or vision loss in advanced countries represen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/55A61P9/00A61P27/02C07D487/04
CPCA61K9/2054A61K9/48A61K9/4866A61K9/4858A61K9/2018C07D487/04A61K31/55A61P27/02A61P43/00A61P9/00
Inventor 萩原昌彦阿贺康弘长谷川道
Owner UBE IND LTD
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