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Formyl peptide-like acceptor-1 regulator and its Preparation and use

A technology of benzamide and methyl group is applied in the field of formyl peptide-like receptor-1 modulators, which can solve the problems such as the discovery of organic small molecule ligands for specific FPRL1 receptors that have not been reported yet.

Inactive Publication Date: 2009-07-01
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, immunomodulatory drug screening research based on FPRL1 receptor agonists and antagonists is also carried out in several famous laboratories in the world. So far, no specific FPRL1 receptor organic small molecule ligands have been reported.

Method used

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  • Formyl peptide-like acceptor-1 regulator and its Preparation and use
  • Formyl peptide-like acceptor-1 regulator and its Preparation and use
  • Formyl peptide-like acceptor-1 regulator and its Preparation and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031]

[0032] Dissolve 0.30g of N-(4-butoxy-benzoyl)-2-amino-benzohydrazide (1) in 10ml of N,N-dimethylacetamide containing 5% glacial acetic acid, add 0.25 g 4-methoxybenzaldehyde, heated at 80°C for 24 hours. After the reaction was completed, the reaction solvent was removed, and the product 2-(4-methoxy-phenyl)-2,3-dihydro-3-(4-butoxy-benzamide)- 1H-Quinazolin-4-one (C1).

[0033] 1 HNMR (300MHz, DMSO-d 6 )δ 0.92(t, 3H), 1.41(m, 2H), 1.67(m, 2H), 3.73(s, 3H), 3.99(t, 2H), 6.11(s, 1H), 6.75(m, 2H) , 6.91 (m, 4H), 7.33-7.68 (m, 6H).

Embodiment 2

[0035]

[0036] 0.30g N-(4-butoxy-benzoyl)-2-amino-benzohydrazide (1) and 0.30g 2,4-dimethoxybenzaldehyde in 10ml of N containing 5% glacial acetic acid, In N-dimethylacetamide, heat the reaction at 50°C for 24 hours to obtain the product 2-(2,4-dimethoxy-phenyl)-2,3-dihydro-3-(4-butane Oxy-benzamide)-1H-quinazolin-4-one (C2).

[0037] 1 HNMR (300MHz, DMSO-d 6 )δ 0.92(t, 3H), 1.42(m, 2H), 1.68(m, 2H), 3.59(s, 3H), 3.72(s, 3H), 4.00(t, 2H), 6.40(s, 1H) , 6.52 (m, 2H), 6.73 (m, 2H), 6.94-7.02 (m, 3H), 7.28 (t, 1H), 7.48 (m, 1H), 7.65 (m, 2H).

Embodiment 3

[0039]

[0040] 0.30g N-(4-butoxy-benzoyl)-2-amino-benzohydrazide (1) and 0.27g 4-dimethylaminobenzaldehyde in 10ml containing 5% glacial acetic acid N, N-di In methylacetamide, heated at 60°C for 24 hours to obtain the product 2-(4-dimethylamino-phenyl)-2,3-dihydro-3-(4-butoxy-benzamide) -1H-quinazolin-4-one (C3).

[0041] 1 HNMR (300MHz, DMSO-d 6 )δ 0.92(t, 3H), 1.42(m, 2H), 1.68(m, 2H), 2.84(s, 6H), 4.00(t, 2H), 6.04(s, 1H), 6.68-6.79(m, 4H), 6.92 (m, 2H), 7.17-7.30 (m, 4H), 7.61 (m, 2H).

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Abstract

The present invention provides a class of substituted quinazolin-4-one compounds described in general formula (A): as well as the preparation method of this class of compounds and as a new class of formyl peptide-like receptor-1 modulators in anti-inflammatory , Immunomodulatory and anti-infective drugs.

Description

technical field [0001] The present invention relates to a class of Formyl Peptide Receptor Like-1 (Formyl Peptide Receptor Like-1, FPRL1) modulators, specifically a class of substituted quinazolinone derivative small molecules that can be used as non-peptide FPRL1 receptor modulators Organic compounds, as formyl peptide-like receptor-1 (FPRL1) modulators, affect the chemotaxis and activation of neutrophils, and play a regulatory role in the body's non-specific and specific inflammatory responses. Background technique [0002] Chemotactic agents produced by tissue cells and microorganisms such as N-formyl peptide (fMLF) can cause the extravasation, chemotaxis and activation of neutrophils, and exert physiological effects through certain signal transduction pathways, including chemotaxis, Inflammatory response, immune regulation and antiviral infection, etc. In the early stage of infection, this kind of chemotactic agent can enhance the body's non-specific immune response abi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/88C07D239/93A61K31/517A61P29/00A61P31/00A61P37/02A61K31/47A61P37/00C07D239/91
CPCC07D239/91A61P29/00A61P31/00A61P37/00
Inventor 王明伟梅江华程希远宣云遐周彩虹叶德全
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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