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Sphingosine-1-phosphate receptor agonist, preparation method thereof and pharmaceutical composition containing same as active ingredient

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 ingredient, can solve the problem of decreased lymphocyte infiltration and achieve therapeutic or preventive immunity Effects of adjustment disorders

Pending Publication Date: 2022-07-15
LG CHEM LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, when S1P1 receptors in lymphocytes are downregulated by S1P1 agonists, lymphocyte expulsion from lymphoid tissue does not occur, resulting in the infiltration of self-aggressive lymphocytes that cause central nervous system (CNS) inflammation and tissue damage reduce

Method used

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  • Sphingosine-1-phosphate receptor agonist, preparation method thereof and pharmaceutical composition containing same as active ingredient
  • Sphingosine-1-phosphate receptor agonist, preparation method thereof and pharmaceutical composition containing same as active ingredient
  • Sphingosine-1-phosphate receptor agonist, preparation method thereof and pharmaceutical composition containing same as active ingredient

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1-1

[0104] Preparation Example 1-1: Synthesis of 7-hydroxy-2H-chromene-3-carbaldehyde

[0105] The title compound was obtained according to the method described in International Patent Publication No. 2010-064707.

[0106] NMR: 1 H-NMR (400 HMz, CDCl 3 );δ9.51(s,1H),7.40(m,5H),7.19(s,1H),7.11(d,1H),6.60(dd,1H),6.49(d,1H),5.10(s, 2H),5.00(s,2H)

preparation example 1-2

[0107] Preparation Example 1-2: Synthesis of (3-chloro-1-isopropyl-1H-indazol-5-yl)-methanol

[0108] The title compound was obtained according to the method described in Korean Registered Patent No. 10-1939657.

[0109] NMR: 1 H-NMR (400HMz, CDCl3); δ 7.64 (s, 1H), 7.43 (m, 2H), 4.79 (m, 3H), 1.83 (br s, 1H), 1.56 (d, 6H)

preparation example 1-3

[0110] Preparation Example 1-3: Synthesis of 7-(3-chloro-1-isopropyl-1H-indazol-5-ylmethoxy)-2H-chromene-3-carbaldehyde

[0111] (3-Chloro-1-isopropyl-1H-indazol-5-yl)-methanol (383 mg, 1.70 mmol) obtained from Preparation Example 1-2 and 7-hydroxy- 2H-chromene-3-carbaldehyde (300 mg, 1.70 mmol) was dissolved in toluene (10 mL), and tributylphosphine (BuP 3 , 291 mg, 1.44 mmol) and 1,1'-(azodicarbonyl)dipiperidine (ADD, 363 mg, 1.44 mmol). After stirring the mixture at room temperature for 18 hours, an excess of hexane was added thereto. The mixture was filtered, and the filtrate was distilled under reduced pressure. The residue was purified by column chromatography to give the title compound (320 mg, 49%).

[0112] NMR: 1 H-NMR (400 HMz, CDCl 3 );δ9.52(s,1H),7.71(s,1H),7.47(dd,J=1.6Hz,1H),7.44(d,1H),7.21(s,1H),7.14(d,1H) ,6.62(dd,J=2.4Hz,1H),6.52(d,1H),5.16(s,2H),5.03(s,2H),4.83-4.76(m,1H),1.57(d,6H)

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Abstract

The present invention relates to a novel compound of chemical formula 1 which acts as a sphingosine-1-phosphate receptor agonist effective in the treatment of autoimmune diseases, a method for preparing the compound, a pharmaceutical composition comprising the compound as an active ingredient, and uses thereof. The compounds of the present invention are effective in the treatment of a wide range of autoimmune diseases and chronic inflammatory diseases, including recurrent-remitting multiple sclerosis, and may also be used in the treatment or prevention of immunomodulatory disorders.

Description

technical field [0001] Cross-reference to related applications [0002] This application claims the benefit of priority based on Korean Patent Application No. 10-2019-0159309 filed on December 3, 2019, the entire disclosure of which is incorporated as a part of the specification. [0003] The present invention relates to a novel compound acting as a sphingosine-1-phosphate receptor agonist useful in the treatment of autoimmune disorders such as multiple sclerosis, a method for its preparation, and a pharmaceutical composition containing the compound as an active ingredient . Background technique [0004] S1P (sphingosine-1-phosphate) is produced by the intracellular ceramide pathway, where ceramide is the starting material. Ceramides are produced by two pathways, the first being the de novo biosynthetic pathway. Ceramides are also produced by the degradation of sphingomyelin, a cell membrane component in cells. S1P levels in each tissue are controlled by two biosynthe...

Claims

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Application Information

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IPC IPC(8): C07D405/12A61K31/4155A61K31/4439A61K31/55C07D405/14A61P25/00A61P29/00A61P37/00
CPCA61P25/00A61P29/00A61P37/00C07D405/12C07D405/14A61K31/4155A61K31/4439A61K31/55A61P37/02
Inventor 白承烨朴德星洪祥墉
Owner LG CHEM LTD
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