Nitrogen-containing heterocyclic compound having kynurenine production inhibitory activity

A technology of nitrogen heterocyclic compounds and kynurenine, which is applied in the field of kynurenine production inhibitors and can solve problems such as tumor growth

Active Publication Date: 2013-01-23
KYOWA HAKKO KIRIN CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are various immune avoidance mechanisms in the microenvironment of the tumor or in the whole body, and when the host tumor fails to be excluded, the tumor grows

Method used

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  • Nitrogen-containing heterocyclic compound having kynurenine production inhibitory activity
  • Nitrogen-containing heterocyclic compound having kynurenine production inhibitory activity
  • Nitrogen-containing heterocyclic compound having kynurenine production inhibitory activity

Examples

Experimental program
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Effect test

reference example 1

[0249] N-(3-Chloroquinoxalin-2-yl)propane-1-sulfonamide (Compound A1)

[0250] Dissolve 2,3-dichloroquinoxaline (5.00g, 25.1mmol) and propane-1-sulfonamide (3.09g, 25.1mmol) in DMSO, add potassium carbonate (3.47g, 25.1mmol), and stir at 150°C 1 hour. Add 1% aqueous acetic acid solution to the reaction mixture, stir at room temperature for 3 hours, filter the resulting solid, wash with water, add diisopropyl ether, and refine the slurry to obtain compound A1 (6.01g, yield 84%) .

reference example 2

[0252] N-(3-Chloroquinoxalin-2-yl)butane-1-sulfonamide (compound A2)

[0253] According to Reference Example 1, compound A2 was obtained from 2,3-dichloroquinoxaline and butane-1-sulfonamide.

reference example 3

[0255] N-(3-Chloroquinoxalin-2-yl)-2-methylpropane-1-sulfonamide (compound A3)

[0256] According to Reference Example 1, compound A3 was obtained from 2,3-dichloroquinoxaline and 2-methylpropane-1-sulfonamide.

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Abstract

Disclosed is a nitrogen-containing heterocyclic compound represented by formula (I) or a pharmacologically acceptable salt thereof, which has kynurenine production inhibitory activity. (In formula (I), R6 and R7 may be the same or different and each represents a hydrogen atom or the like; R8, R9, R10 and R11 may be the same or different and each represents a hydrogen atom or the like; R1 represents a lower alkyl group which may be substituted by a cycloalkyl group, or the like; and R3 represents an optionally substituted aryl group or an optionally substituted heterocyclic group.)

Description

technical field [0001] The present invention relates to a nitrogen-containing heterocyclic compound having a kynurenine production inhibitory effect or a pharmacologically acceptable salt thereof, and a kynurenine production inhibitor containing one or more of them as an active ingredient. Background technique [0002] Cancer cells overexpress tumor-associated antigens. It is believed that the host immune system responds to such tumor-associated antigens, and eliminates tumors through cellular immunity. However, various immune avoidance mechanisms exist in the microenvironment of the tumor or in the whole body, and when the host tumor fails to be eliminated, the tumor grows. [0003] Recently, it has been reported that indoleamine-2,3-dioxygenase (IDO), which is a tryptophan metabolizing enzyme, inhibits the proliferation of T cells and NK cells, and also reduces host immunity by activating regulatory T cells. . IDO is highly expressed in tumor tissues, and its expression...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12A61K31/517A61P1/04A61P11/06A61P17/04A61P19/02A61P21/02A61P25/00A61P25/24A61P25/28A61P29/00A61P31/00A61P31/04A61P31/10A61P31/12A61P35/00A61P37/06A61P37/08C07D401/14C07D403/12C07D405/12C07D413/14C07D471/04
CPCC07D401/14C07D401/12C07D413/14C07D403/12C07D405/12C07D471/04C07D417/12C07D241/44A61K31/498A61K31/506A61P1/04A61P11/06A61P17/04A61P19/02A61P21/02A61P25/00A61P25/24A61P25/28A61P29/00A61P31/00A61P31/04A61P31/10A61P31/12A61P35/00A61P37/04A61P37/06A61P37/08Y02A50/30A61K31/517
Inventor 福田裕一金井寿美中里宜资金原庆辅
Owner KYOWA HAKKO KIRIN CO LTD
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