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Preparation and application of aminopyrimidine derivative selectively targeting CDK9

A kind of technology selected from, group, applied in the field of aminopyrimidine derivatives and preparation thereof, can solve the problems such as no relevant reports, and achieve the effect of good selectivity and good anti-proliferative activity

Pending Publication Date: 2021-10-29
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to neutropenia, the clinical trial of BAY-1143572 has been terminated, and the cause of this side effect has not been reported yet

Method used

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  • Preparation and application of aminopyrimidine derivative selectively targeting CDK9
  • Preparation and application of aminopyrimidine derivative selectively targeting CDK9
  • Preparation and application of aminopyrimidine derivative selectively targeting CDK9

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Example 1: Compound LW-001

[0055]

[0056] 1 H NMR (300MHz, CDCL 3 ):δ(ppm)=8.83(s,1H),8.00(s,1H),7.89-7.81(m,4H),7.65(s,1H),6.82-6.76(m,2H),3.96(s, 3H),3.83(s,4H),3.65(d,J=6.0Hz,2H),2.75(s,2H),2.67-2.50(m,4H).

Embodiment 2

[0057] Example 2: Compound LW-002

[0058]

[0059] 1 H NMR (300MHz, CDCL 3 ):δ(ppm)=9.04(s,1H),8.67(s,1H),7.86-7.80(m,5H),7.65(s,1H),6.89-6.74(m,2H),3.98(s, 3H), 3.65(d, J=6.0Hz, 2H), 3.01(s, 4H), 2.51-2.45(m, 6H), 2.14(s, 3H), 1.65-1.62(m, 2H).

[0060] Example 3: Compound LW-003

[0061]

[0062] 1 H NMR (300MHz, CDCL 3 ):δ(ppm)=8.83(s,1H),8.02(s,1H),7.88-7.81(m,4H),7.73(s,1H),7.12(s,1H),6.82-6.76(m, 2H),3.96(s,3H),3.65-3.59(m,2H),2.76-2.65(m,10H),2.39(s,3H).

[0063] Example 4: Compound LW-004

[0064]

[0065] 1 H NMR (300MHz, CDCL 3 ):δ(ppm)=8.91(s,1H),8.07(s,1H),7.87-7.80(m,4H),7.71(s,1H),7.15(s,1H),6.83-6.78(m, 2H),3.96(s,3H),3.60-3.53(m,2H),2.34-2.30(m,3H),2.18(s,3H),2.02-1.96(m,6H).

[0066] Embodiment 5: Compound LW-005

[0067]

[0068] 1 H NMR (300MHz, CDCL 3 ):δ(ppm)=8.98(s,1H),8.03(s,1H),7.87-7.82(m,4H),7.73(s,1H),7.12(s,1H),6.83-6.77(m, 2H),3.96(s,3H),3.60-3.54(m,2H),2.51-2.47(m,2H),2.42(s,4H),1.49-1.39(m,6H).

[0069] Embodiment 6: ...

Embodiment 11

[0084] Example 11: Compound LW-011

[0085]

[0086] 1 H NMR (300MHz, DMSO-d 6 ): δ(ppm)=8.85(s,1H),8.68(s,1H),8.64(t,J=6.0Hz,1H),7.98-7.88(m,5H),7.16(d,J=12.0Hz ,1H),6.97-6.92(m,1H),3.98(s,3H),3.72(m,2H)

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PUM

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Abstract

The invention discloses preparation and application of an aminopyrimidine derivative selectively targeting CDK9, in particular, a preparation method of the compound and application of the compound in prevention and / or treatment of tumor-related diseases including glioma, various leukemia, lymphoma, liver cancer, stomach cancer, prostate cancer, ovarian cancer, breast cancer, lung cancer and the like. The compound can effectively and selectively inhibit the activity of CDK9 protein, and meanwhile, the compound shows remarkable anti-tumor activity in cancer cells such as MV4-11, MCF-7 and MOLM-13.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, and specifically includes aminopyrimidine derivatives capable of effectively inhibiting CDK9 protein activity, a preparation method and application thereof. Background technique [0002] Cyclin-dependent kinases (CDKs) are key protein kinases in cell cycle regulation, which can effectively regulate DNA synthesis and mitosis. Combining with the corresponding chaperones to form a complex is a necessary condition for CDK protein function. According to their main functions, CDKs can be divided into periodic CDKs (including CDK1, CDK2, CDK3, CDK4, and CDK6) and transcriptional CDKs (including CDK7, CDK8, CDK9, CDK11, CDK12, CDK13, CDK19, etc.). Studies have shown that many cancers have "transcriptional addiction", so transcriptional CDKs have recently attracted attention. Among them, CDK9 protein is widely involved in the initiation, elongation and termination stages of transcription. In particula...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D251/22C07D403/12C07D405/12C07D401/12C07D405/14C07D239/42A61K31/5377A61K31/551A61K31/53A61K31/55A61K31/505A61K31/506A61P35/00A61P35/02A61P31/12A61P31/18A61P31/14A61P31/22A61P31/20
CPCC07D251/22C07D403/12C07D405/12C07D401/12C07D405/14C07D239/42A61P35/00A61P35/02A61P31/12A61P31/18A61P31/14A61P31/22A61P31/20
Inventor 李志裕卞金磊吴体智喻彬杜泽坤张立翱
Owner CHINA PHARM UNIV
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