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Preventive/remedy for retinal nerve diseases containing alkyl ether derivatives or salts thereof

Inactive Publication Date: 2006-09-14
TOYAMA CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

"The present invention relates to a new compound, called an alkyl ether derivative, which has the effect of protecting retinal nerve cells. This compound can be used as a preventive or remedy for retinal nerve diseases. The compound has a specific formula and can be modified by various groups. The invention also includes a method for making the compound and a pharmaceutical composition containing it."

Problems solved by technology

When pathologic lesion occurs on the retina, eyesight fails, sometimes resulting in blindness.

Method used

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  • Preventive/remedy for retinal nerve diseases containing alkyl ether derivatives or salts thereof
  • Preventive/remedy for retinal nerve diseases containing alkyl ether derivatives or salts thereof
  • Preventive/remedy for retinal nerve diseases containing alkyl ether derivatives or salts thereof

Examples

Experimental program
Comparison scheme
Effect test

production example 1

Production of 1-(2-(2-(1-benzothiophene-5-yl)ethoxy)ethyl)-3-azetidinol

[0143] (1) 1.20 g of 2-(2-(1-benzothiophene-5-yl)ethoxy)acetic acid was dissolved in 12 ml of methylene chloride. Thereafter, 2.3 ml of triethylamine and 0.38 g of imidazole were added to the obtained solution, and the mixture was then cooled to 5° C. Thereafter, 0.41 ml of thionyl chloride was added dropwise thereto, and the obtained mixture was stirred at the same above temperature for 1 hour. The reaction mixture was cooled to −60° C., and thereafter, 0.82 ml of triethylamine and 0.72 g of 3-azetidinol hydrochloride were added thereto. The mixture was stirred at the same above temperature for 1 hour and then at a room temperature for 1.5 hours. Thereafter, water was added to the reaction mixture, and the pH thereof was adjusted to pH 1.0 by addition of 6 mol / l hydrochloric acid. Thereafter, an organic layer was separated. The organic layer was washed with a saturated saline solution and then dried over anhydr...

production example 2

Production of 1-(2-(2-(1-benzothiophene-5-yl)ethoxy)ethyl)-3-azetidinol hydrochloride

[0147] 1.03 g of 1-(2-(2-(1-benzothiophene-5-yl)ethoxy)ethyl)-3-azetidinol was dissolved in 4.2 ml of ethyl acetate. Thereafter, 0.86 ml of an ethyl acetate solution containing 4.76 mol / l dry hydrogen chloride was added to the obtained solution, and the obtained mixture was stirred at a room temperature for 1 hour, and then at 5° C. for 1 hour. Thereafter, precipitated crystals were collected by filtration, washed with ethyl acetate, and then dried, so as to obtain 0.98 g of 1-(2-(2-(1-benzothiophene-5-yl)ethoxy)ethyl)-3-azetidinol hydrochloride.

[0148] Melting point: 101° C. to 102° C.

[0149] IR (KBr)cm−1: 3132, 2952, 1423, 1340, 1158, 814, 701

[0150] NMR (CDCl3)δppm: 2.97 (2H, t, J=7 Hz), 3.2-3.3 (2H, m), 3.69 (2H, t, J=7 Hz), 3.6-3.8 (2H, m), 3.9-4.1 (2H, m), 4.2-4.4 (2H, m), 4.6-4.8 (1H, m), 7.18 (1H, dd, J=1, 8 Hz), 7.29 (1H, d, J=5 Hz), 7.41 (1H, d, J=5 Hz), 7.65 (1H, d, J=1 Hz), 7.78 (1H, d,...

production example 3

Production of 1-(3-(2-(1-benzothiophene-6-yl)ethoxy)propyl)-3-azetidinol

[0151] 1.00 g of 6-(2-(3-chloropropoxy)ethyl)-1-benzothiophene was dissolved in 5 ml of dimethyl sulfoxide. Thereafter, 0.86 g of 3-azetidinol hydrochloride and 1.63 g of potassium carbonate were added to the obtained solution, and the obtained mixture was stirred at 75° C. for 2.5 hours, and then at 95° C. for 1.5 hours. Thereafter, the reaction solution was cooled, and thereafter, water and ethyl acetate were added to the reaction mixture. The pH of the obtained mixture was adjusted to pH 1 by addition of 6 mol / l hydrochloric acid, and a water layer was then separated. Ethyl acetate was added to the water layer, and the pH of the obtained mixture was adjusted to pH 10 by addition of a 2 mol / l aqueous sodium hydroxide solution, followed by separation of an organic layer. The organic layer was successively washed with water and a saturated saline solution, and then dried over anhydrous magnesium sulfate. Therea...

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PUM

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Abstract

An alkyl ether derivative represented by the following general formula [1]or its salt: wherein R1 and R2 represent each a substituent such as hydrogen, halogeno or alkyl; R3 represents alkylamino, amino or hydroxyl; the ring A represents a 5- or 6-membered aromatic heterocycle or a benzene ring; m and n are each an integer of from 1 to 6; and p is an integer of from 1 to 3; shows an effect of protecting retinal nerve cells and, therefore, is useful as a preventive and / or a remedy for retinal nerve diseases such as glaucoma, diabetic retinopathy, retinal artery obstruction, retinal venous obstruction, macular degeneration and retinopathy of prematurity.

Description

TECHNICAL FIELD [0001] The present invention relates to a preventive and / or remedy for retinal nerve diseases, which comprise a novel alkyl ether derivative or a salt thereof as an active ingredient. BACKGROUND ART [0002] The retina acting as a photoreceptive tissue is located at the inner surface of the wall of eyeball. When pathologic lesion occurs on the retina, eyesight fails, sometimes resulting in blindness. Such retina is broadly divided into sensory retina and retinal pigment epithelium. Such sensory retina is divided into 9 layers, and comprises visual cells as first neuron, bipolar cells as second neuron, ganglion cells as third neuron, and other cells (Hyojun Ganka Gaku, 7th edition, pp. 103-107, Igaku-Shoin Ltd., 1998). [0003] Various retinal diseases are developed depending on the causes of diseases or onset forms. Examples of a disease affecting the retinal nerve may include glaucoma, diabetic retinopathy, retinal artery obstruction, retinal venous obstruction, macular...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/397A61K31/445A61K31/452A61K31/453A61K31/4025A61K31/40A61K31/435A61K31/4525A61K31/4535A61P9/10A61P27/02C07D207/12C07D405/12C07D409/12
CPCA61K31/397A61K31/40A61K31/4025A61K31/435A61K31/4525A61K31/4535C07D207/12C07D405/12C07D409/12Y10S514/912Y10S514/913A61P25/00A61P27/00A61P27/02A61P27/06A61P43/00A61P7/02A61P9/00A61P9/10
Inventor KIMURA, TATSUOIWAKAMI, NOBORUSAITOH, AKIHITO
Owner TOYAMA CHEM CO LTD
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