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Casr agonist

A technology of substituents, glutamic acid, applied in the field of CaSR agonists

Active Publication Date: 2011-11-09
EA PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no literature documenting its relationship with "calcium-sensing receptor (CaSR) or G protein-conjugated receptor", "a strong taste", "diarrhea (syndrome) or hyperparathyroidism", which are the characteristics of the present invention

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0171] Examples are given below to illustrate the present invention in more detail, but these examples do not limit the present invention.

[0172] In the present specification, the conventional method refers to a method generally used as a chemical operation represented by liquid separation operation, drying, filtration, and concentration.

[0173] In this specification, purification step A means that the crude product obtained by a conventional method is supplied to reversed-phase high-performance liquid chromatography using octadecyl chemically bonded silica gel (ODS) as a filler, and is purified with 0.1% trifluoroacetic acid ( The mixed solution of water and acetonitrile of v / v) is eluted, the method for concentrating, freeze-drying target component.

[0174] Hereinafter, examples are given for the synthesis of typical compounds of the present invention shown in Table 1 for further details, but the compounds of the present invention are not limited to these Examples.

[...

Synthetic example 1

[0180] (Synthesis Example 1) N 5 Synthesis of -(3-sulfophenyl)-L-glutamine (Compound No.1)

[0181] 75 mg (0.247 mmol) Boc-Glu-OtBu, 112 mg (0.296 mmol) HATU, 41 mg (0.296 mmol) HOAt were dissolved in 1 ml DMF, 52 μl triethylamine was added, and stirred at room temperature for 10 minutes. 43 mg (0.247 mmol) of 3-sulfoaniline was added thereto, followed by stirring at room temperature overnight. After distilling off the solvent, the obtained intermediate was purified by purification step A, dissolved in 2 ml of trifluoroacetic acid, stirred at room temperature for 3 hours, and then the solvent was distilled off. The product was purified by Purification Step A to afford the title compound.

[0182] Yield: 30.8 mg (0.10 mmol), yield: 41%.

[0183] 1H-NMR (D2O, 300MHz): δ7.89(s, 1H), 7.67-7.62(m, 2H), 7.58-7.53(m, 1H), 3.99(t, 1H, J=6.4Hz), 2.73- 2.66(m, 2H), 2.33-2.25(m, 2H)ESI(m / z): 303[M+H]+, 301[M-H]-

Synthetic example 2

[0184] (Synthesis Example 2) N 5 Synthesis of -(4-methoxy-3-sulfophenyl)-L-glutamine (Compound No.2)

[0185] Using p-anisidine-3-sulfonic acid instead of 3-sulfoaniline in Synthesis Example 1, the same operation was carried out to obtain the title compound.

[0186] Yield: 24.7 mg, yield: 23%.

[0187] 1H-NMR (D2O, 300MHz): δ7.96(s, 1H), 7.53(d, 1H), 7.04(d, 1H), 3.98(t, 1H), 3.78(s, 3H), 2.63-2.52( m, 2H), 2.30-2.05 (m, 2H)

[0188] ESI(m / z): 333[M+H]+

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Abstract

Many variations of compounds having CaSR agonistic activity are searched and a CaSR agonist agent, a pharmaceutical composition, a preventive or therapeutic agent for diarrhea, and a kokumi taste-imparting agent containing the compound are provided. The CaSR agonist agent, pharmaceutical composition, preventive or therapeutic agent for diarrhea, and kokumi taste-imparting agent, characterized by containing a glutamic acid derivative or a pharmaceutically acceptable salt thereof having CaSR agonistic activity.

Description

technical field [0001] The present invention relates to a glutamic acid derivative having CaSR agonistic activity or a pharmaceutically acceptable salt thereof, and a CaSR agonist containing the derivative or a pharmaceutically acceptable salt thereof as an active ingredient, a pharmaceutical composition, and a diarrhea medicine A prophylactic or therapeutic drug and a kokumi (コク味) administering agent. Background technique [0002] Calcium Sensing Receptor (Calcium Sensing Receptor: CaSR) is also called calcium receptor, and the receptor signal regulates various functions in organisms. There is a possibility that substances having CaSR agonistic activity can be used for the treatment or prevention of various diseases, and Possibility of use as a kokumi imparting agent. Patent Document 1 discloses a screening method for a kokumi-imparting substance and a kokumi-imparting agent containing the kokumi-imparting substance obtained by this method. Furthermore, it is also describ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/04A23L1/228A61K31/198A61K31/662A61P1/12A61P43/00C07C309/51C07F9/38C07F9/40A23L27/00A23L27/20A23L27/22
CPCA23L1/22657C07F9/4021C07F9/4018C07C309/51A23L1/3051C07C237/04A23L1/228C07F9/3834A23L27/22A23L33/175A23L27/204A61P1/10A61P1/12A61P43/00
Inventor 杉木正之冈松亭S·朝里河户弥生畑中敏宏矢野彻雄关幸惠宫村直宏长崎浩明江藤让安田礼子
Owner EA PHARMA CO LTD
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