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TLR (Toll-like receptor) modulators, pharmaceutical composition thereof, preparation method and application

A solvate and compound technology, applied in the field of compounds with toll-like receptor modulating effects, can solve problems such as retrovirus damage

Active Publication Date: 2018-11-13
北京施安泰医药技术开发有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, a gene encoding a protein similar to TLR10 in humans is present in mice, but the gene appears to have been damaged at one point by a retrovirus in the past

Method used

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  • TLR (Toll-like receptor) modulators, pharmaceutical composition thereof, preparation method and application
  • TLR (Toll-like receptor) modulators, pharmaceutical composition thereof, preparation method and application
  • TLR (Toll-like receptor) modulators, pharmaceutical composition thereof, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] Preparation of 2-(morpholinyl-4-carbonyl)imidazo[1,2-a]quinoxalin-4(5H)-one

[0082]

[0083] first step:

[0084] Compound 1a (16.1g, 100mmol), 1b (19.5g, 100mmol) was dissolved in ethanol (200ml), heated to reflux, stirred and reacted for 8 hours, TLC detected the reaction, concentrated under reduced pressure after the reaction was completed, and separated by column chromatography to obtain Off-white solid 20.3g, yield 79.0%.

[0085] Step two:

[0086] Compound 1c (20.0g, 77.7mmol) obtained in the first step was dissolved in a mixed solvent of ethanol (100ml) and water (100ml), and sodium hydroxide (6.2g, 155.5mmol) was added at room temperature, and the reaction was stirred at 40°C 6 Hours, TLC detection reaction, after the completion of the reaction, ethanol was removed under reduced pressure, the remaining solution was poured into stirred dilute hydrochloric acid, the solid was precipitated, filtered, the filter cake was washed with water, and dried to obtain...

Embodiment 2

[0090] The preparation of compound 2-(4-methylpiperidinyl-1-carbonyl) imidazo[1,2-a]quinoxalin-4(5H)-one shown in the following formula: the method of reference example 1 is prepared , MS-ESI: m / z=312.3 [M+1].

[0091]

Embodiment 3

[0093] The preparation of the compound 2-(4-piperidinyl-1-carbonyl)imidazo[1,2-a]quinoxalin-4(5H)-one represented by the following formula: it was prepared by referring to the method of Example 1, MS - ESI: m / z = 298.3 [M+1].

[0094]

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PUM

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Abstract

The invention belongs to the field of pharmaceutical chemistry, particularly relates to compounds with TLR (Toll-like receptor) modulation effect as well as a preparation method and an application ofthe compounds, and provides compounds represented by the following formula X in the description. The compounds of formula X can be used as the TLR modulators and have higher activity. Besides, the compounds have the characteristics of high efficiency, low toxicity, resistance to drug resistance and the like, and have clinical application value. Moreover, synthesis steps of the compounds are simple, so that the compounds have higher economic utilization value.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and specifically relates to a class of compounds with toll-like receptor regulating effects, pharmaceutical compositions, preparation methods and uses thereof. Background technique [0002] Toll-like receptors (Toll-like receptors, TLR) are an important class of protein molecules involved in nonspecific immunity (innate immunity), and are also a bridge connecting nonspecific immunity and specific immunity. TLRs are single transmembrane non-catalytic proteins that recognize molecules with conserved structures derived from microorganisms. When microorganisms break through the body's physical barriers, such as skin, mucous membranes, etc., TLR can recognize them and activate the body to generate immune cell responses. Toll-like receptors are characterized by an extracellular leucine-rich domain and a major transmembrane protein with a cytoplasmic extension containing a conserved region. The inna...

Claims

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Application Information

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IPC IPC(8): C07D487/04C07D471/14A61K31/4985A61K31/5377A61P31/12A61P35/00A61P37/06A61P37/02A61P25/24
CPCA61P25/24A61P31/12A61P35/00A61P37/02A61P37/06C07D471/14C07D487/04
Inventor 王加维田从凡王霞
Owner 北京施安泰医药技术开发有限公司
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