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Sphingosine-1-phosphate receptor agonists, methods of preparing the same, and pharmaceutical compositions containing the same as an active agent

A compound and pharmaceutical technology, applied in the field of sphingosine-1-phosphate receptor agonist, its preparation and pharmaceutical composition containing it as an active agent, can solve problems such as decreased infiltration of autoimmune lymphocytes

Active Publication Date: 2015-11-11
LG CHEM LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, if S1P1 receptors in lymphocytes are downregulated by S1P1 agonists, lymphocytes do not leave lymphoid tissue, resulting in a reduced infiltration of autoimmune lymphocytes that lead to central nervous system (CNS) inflammation and tissue damage

Method used

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  • Sphingosine-1-phosphate receptor agonists, methods of preparing the same, and pharmaceutical compositions containing the same as an active agent
  • Sphingosine-1-phosphate receptor agonists, methods of preparing the same, and pharmaceutical compositions containing the same as an active agent
  • Sphingosine-1-phosphate receptor agonists, methods of preparing the same, and pharmaceutical compositions containing the same as an active agent

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1-1

[0328] Preparation 1-1: Synthesis of methyl 1-isopropyl-1H-indole-5-carboxylate

[0329] At 0°C, 1H-indole-5-carboxylic acid methyl ester (1g, 5.71mmol) was dissolved in dimethylformamide (20mL), and isopropyl iodide (1.14mL, 11.42mmol ) and sodium hydride (205 mg, 8.56 mmol). The mixture was stirred at 50°C for 8 hours, 1N hydrochloric acid solution was added, and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was distilled under reduced pressure and separated by column chromatography to obtain the title compound (1.1 g, 89%).

[0330] NMR: 1H-NMR (400HMz, CDCl 3 ); 3H), 1.54(d, 6H)

preparation example 1-2

[0331] Preparation 1-2: Synthesis of 1-isopropyl-1H-indole-5-carboxylic acid

[0332] The compound (1.1 g, 5.06 mmol) obtained from Preparation Example 1-1 was dissolved in a mixed solution of tetrahydrofuran and methanol (2 / 1, 20 mL), and 1N aqueous sodium hydroxide solution (10 mL, 10.12 mmol) was slowly added dropwise thereto . The mixture was stirred at room temperature for 18 hours, 1N hydrochloric acid solution was added, and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was distilled under reduced pressure to obtain the title compound (900 mg, 88%).

[0333] NMR: 1H-NMR (400HMz, CDCl 3 ); 6H)

preparation example 1-3

[0334] Preparation Example 1-3: Synthesis of 3-[4-(N-hydroxyformamidoyl (carbimidoyl))-3-methyl-phenyl]-propionic acid ethyl ester

[0335] The title compound was obtained by the method described in EP2202232.

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PUM

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Abstract

The present invention relates to novel compounds of Formula 1 as sphingosine-1-phosphate receptor agonists which can be effectively used for the treatment of autoimmune diseases, a method for preparing the same, and a pharmaceutical composition comprising the same as an active component. The compounds according to the present invention are effective on extensive autoimmune diseases and chronic inflammatory diseases including relapsing-remitting multiple sclerosis, and can also be used for treating or preventing immunoregulation disorders.

Description

technical field [0001] The present invention relates to novel compounds which are agonists of the sphingosine-1-phosphate receptor, which can be effectively used in the treatment of autoimmune diseases such as multiple sclerosis, and to processes for the preparation of said compounds and to compounds comprising said compounds as Pharmaceutical composition of active ingredients. Background technique [0002] S1P (sphingosine-1-phosphate) is produced via the intracellular ceramide pathway with ceramide as the starting material. Ceramides are produced via two pathways, the first being the de novo biosynthetic pathway. Ceramides are also produced in cells by the degradation of the cell membrane component sphingomyelin. S1P levels in each tissue are controlled by two biosynthetic sphingosine kinases (SphK) and two biodegradable S1P phosphatases (S1P lyase and lysophospholipid phosphatase). SlP, produced by phosphorylation of sphingosine by sphingosine kinase, is known to media...

Claims

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Application Information

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IPC IPC(8): C07D413/04C07D271/12A61K31/4245A61P37/00
CPCC07D413/04C07D209/08C07D209/30C07D231/56C07D401/12C07D403/12C07D413/14C07D471/04A61P1/04A61P1/16A61P17/00A61P17/02A61P19/02A61P21/00A61P25/00A61P29/00A61P37/00A61P37/06A61P43/00A61P9/10A61K31/4245
Inventor 白承烨李成培朴德星李沅炯
Owner LG CHEM LTD
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