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Imidazopyridine compounds, as well as preparation method and application thereof

A technology of imidazopyridine and compounds, applied in the field of imidazopyridine compounds, can solve the problems of low patient survival rate and poor prognosis of breast cancer patients

Inactive Publication Date: 2012-09-19
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

Kang et al. (Kang H, Watkins G, Dougl as-Jones A, et al. The elevated level of CXCR4 is correlated with nod al metastasis of human breast cancer. Breast, 2005, 14(5): 360-367) passed the detection of 120 cases The expression of CXCR (CXC-like chemokine receptor) in breast cancer tissue found that the positive expression of CXCR4 was associated with lymph nodes and distant metastasis in patients; Li et al. (Li YM, Pan Y, wei Y, et al. Upregulation of CXCR4 is essential for HER2-mediated tumor metastasis. Cancer Cell, 2004, 6(5): 459-469) found that breast cancer patients with high expression of CXCR4 had a poorer prognosis
A study on colorectal cancer showed that high expression of CXCR4 was associated with tumor recurrence and liver metastasis, and the corresponding patient survival rate was also lower (Kim J, Takeuchi H, LamST, et al. Chemokine receptor CXCR4 expression in colorectal cancer patients increases the risk for recurrence and for poor survival. J Clin Oncol, 2005, 23(12): 2744-2753)

Method used

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  • Imidazopyridine compounds, as well as preparation method and application thereof
  • Imidazopyridine compounds, as well as preparation method and application thereof
  • Imidazopyridine compounds, as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0145] Compound 1: N 1 -((7-(4-methylpiperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)methyl)-N 1 -((3-methylpyridin-2-yl)methyl)butane-1,4-diamine

[0146]

[0147] Step 1: 2-Amino-3-nitro-4-chloropyridine

[0148] Under stirring at 0°C, concentrated nitric acid (5.00 g, 0.0389 mol) and concentrated sulfuric acid (3.89 g, 0.0389mol), the addition was completed, and the mixture was naturally raised to room temperature and stirred for 1 hour. Then the reaction solution was poured into a mixture of 200 g of ice and 100 ml of water, and a large amount of yellow solids were precipitated, which were collected by filtration. The filtrate was neutralized with 28% ammonia water to pH 9, then extracted three times with ethyl acetate, and the organic phase was collected. The solid obtained by filtration was also dissolved in ethyl acetate, and the pH was adjusted to 9 with ammonia water, the separated organic phase was combined with the aforementioned organic phase, dried over anhyd...

Embodiment 2

[0172] Compound 2: N 1 -((7-(4-methylpiperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)methyl)-N 1 -(pyridin-2-ylmethyl)butane-1,4-diamine

[0173] The reaction process was the same as in Example 1, except that 2-pyridinecarbaldehyde was used instead of 3-methyl-2-pyridinecarbaldehyde in step 7 to obtain a pale yellow gum.

[0174] 1 H NMR (300MHz, CDCl 3, ppm): δ8.56 (d, 1H, J = 4.2Hz), 7.96 (d, 1H, J = 6.0Hz), 7.54 (t, 1H, J = 7.5Hz), 7.33 (d, 1H, J = 7.8Hz), 7.11(t, 1H, J=6.0Hz), 6.35(d, 1H, J=5.7Hz), 5.58(brs, 2H), 3.89(s, 2H), 3.88(s, 4H), 3.78 (s, 2H), 2.61-2.53 (m, 8H), 2.32 (s, 3H), 1.57-1.50 (m, 2H), 1.45-1.41 (m, 2H); EI-MS: 408 (M) +

Embodiment 3

[0176] Compound 3: N 1 -(2-Methylphenyl)-N 1 -((7-(4-methylpiperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)methyl)butane-1,4-diamine

[0177] The reaction process was the same as in Example 1, except that 2-methylbenzaldehyde was used instead of 3-methyl-2-pyridinecarbaldehyde in step 7 to obtain a colorless gum.

[0178] 1 H NMR (300MHz, CDCl 3 , ppm): δ7.91 (brs, 0.5H, imidazole NH), 7.80 (d, 1H, J=5.7Hz), 7.39 (brs, 0.5H, imidazole NH), 7.32 (d, 1H, J=7.2Hz ), 7.07-6.95(m, 3H), 6.29(d, 1H, J=5.7Hz), 5.41(brs, 2H), 3.90(s, 4H), 3.78(s, 2H), 3.60(s, 2H) , 2.71(s, 2H), 2.59(s, 4H), 2.46(s, 2H), 2.34(s, 3H), 2.24(s, 3H), 1.56(s, 4H); ESI-MS: 422.6(M +H) +

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Abstract

The invention discloses 2,7-substituted 3H-imidazole[4,5-b]pyridine compounds shown as the structural formula I, or pharmaceutically acceptable salt, ester and precursors, and / or hydrate and medicinal compositions thereof, and a preparation method for the compounds. The compounds, or pharmaceutically acceptable salt, ester and precursors, and / or hydrate and medicinal compositions thereof can serve as antagonists of CR4 and are used for treating or preventing CXCR4 receptor activation related diseases.

Description

technical field [0001] The present invention relates to imidazopyridine compounds, their pharmaceutical compositions and their preparation methods and applications. These compounds can be used as CXCR4 antagonists to mediate any medical conditions regulated by CXCR4 receptor signals. Background technique [0002] HIV (human immunodeficiency virus) relies on the CD4 (surface antigen cluster of differentiation 4 receptor) receptor and at least one co-receptor expressed on the surface of the cell membrane to enter the host cell. M-tropic strains of HIV virus (pro-M strains) utilize the chemokine receptor CCR5 (CC-like chemokine receptor 5), while T-tropic strains of HIV (pro-T strains) mainly utilize CXCR4 (CXC-like chemokine receptors). Factor receptor 4) as a co-receptor, the function of the HIV co-receptor mainly depends on the V3 (the third variable region on gp120) loop on the viral outer membrane protein gp120 (HIV viral outer membrane protein molecular weight is 120KD) ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A61K31/496A61P31/18A61P19/02A61P29/00A61P35/00
CPCY02P20/55
Inventor 龙亚秋曹斌谢欣魏巍
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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