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Pyrrolopyrimidine derivative as well as preparation method and application thereof

A technology of compounds and hydrates, applied in chemical instruments and methods, drug combinations, pharmaceutical formulations, etc., can solve problems such as no clinical research reports, and achieve good inhibition, good inhibition effect, and good cell proliferation effect

Inactive Publication Date: 2021-07-09
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Both in vivo and in vitro studies of TAE-226 have shown that it has good anti-tumor activity and can improve the survival rate of animals in meningioma animals, but there is no clinical research report

Method used

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  • Pyrrolopyrimidine derivative as well as preparation method and application thereof
  • Pyrrolopyrimidine derivative as well as preparation method and application thereof
  • Pyrrolopyrimidine derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0097] Example 1: N-ethyl-4-((4-((1-methyl-2-oxo-1,2-dihydropyridin-3-yl)amino)-7H-pyrrole[2,3-d ]pyrimidin-2-yl)amino)benzenesulfonamide

[0098]

[0099] 1 H NMR (600MHz, DMSO-d 6 )δ11.52(s,1H),9.54(s,1H),8.71(dd,J=7.4,1.5Hz,1H),8.38(s,1H),8.01(d,J=8.9Hz,2H), 7.65(d, J=8.9Hz, 2H), 7.40(dd, J=6.8, 1.7Hz, 1H), 7.30(t, J=5.8Hz, 1H), 7.06(dd, J=3.4, 2.3Hz, 1H ),6.56(dd,J=3.4,1.9Hz,1H),6.32(t,J=7.1Hz,1H),3.58(s,3H),2.76(dt,J=13.1,6.5Hz,2H),0.97 (t,J=7.2Hz,3H).ESI-MS m / z:440.1[M+H] + .

[0100] synthetic route

[0101]

[0102] Reagents and conditions: a) CH 3 I, NaH, anhydrous THF, 55°C; b) Pd / C, H 2 , MeOH, 40℃; c) Ts-Cl, NaH, anhydrous THF, 0℃; d) 1-3, DIPEA, DMF, 100℃; e) Pd(AcO) 2 ,X-phos,Cs 2 CO 3 , dioxane, 90°C; f) NaOH, MeOH / H 2 O, 40°C.

[0103] a) Dissolve 3-nitropyridin-2(1H)-one (14.2mmol) in 30mL of anhydrous tetrahydrofuran, add sodium hydride (18.5mmol) in batches under stirring at 0°C, and react for 0.5h. Then iodomethane (16.9 mmol) was added ...

Embodiment 2

[0110] Example 2: N-(4-((4-((4-((1-methyl-2-oxo-1,2-dihydropyridin-3-yl)amino)-7H-pyrrole[2,3 -d]pyrimidin-2-yl)amino)phenyl)acetamide

[0111]

[0112] 1 H NMR (600MHz, DMSO-d 6 )δ11.34(s,1H),11.34(s,1H),9.77(s,1H),9.77(s,1H),8.94(s,1H),8.94(s,1H),8.74(d,J =6.6Hz,1H),8.74(d,J=6.6Hz,1H),8.25(s,1H),8.25(s,1H),7.70(d,J=8.9Hz,2H),7.70(d,J =8.9Hz,2H),7.45(d,J=8.9Hz,2H),7.45(d,J=8.9Hz,2H),7.35(dd,J=6.8,1.7Hz,1H),7.35(dd,J =6.8,1.7Hz,1H),6.97(dd,J=3.4,2.3Hz,1H),6.48(dd,J=3.4,1.9Hz,1H),6.29(t,J=7.1Hz,1H),3.57 (s,3H),2.02(s,3H).ESI-MS m / z:390.2[M+H] + .

Embodiment 3

[0113] Example 3: 1-methyl-3-((2-((1-methyl-1H-pyrazol-4-yl)amino)-7H-pyrrole[2,3-d]pyrimidin-4-yl) Amino)pyridin-2(1H)-one

[0114]

[0115] 1 H NMR (600MHz, DMSO-d 6 )δ11.23(s,1H),8.82(s,1H),8.69(s,1H),8.22(s,1H),7.90(s,1H),7.50(s,1H),7.35(dd,J =6.7,1.4Hz,1H),6.92(dd,J=3.4,2.3Hz,1H),6.44(dd,J=3.3,1.8Hz,1H),6.31(t,J=7.1Hz,1H),3.80 (s,3H),3.57(s,3H).ESI-MS m / z:337.2[M+H] + .

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Abstract

The invention belongs to the technical field of medicines, and provides a compound shown as a general formula (I), geometric isomers or pharmaceutically acceptable salts, hydrates, solvates and prodrugs thereof, and preparation methods thereof, wherein A, B and R1 are described in the claims and the specification. The compound and the geometric isomer thereof or the pharmaceutically acceptable salt, hydrate, solvate, prodrug or pharmaceutical composition thereof have the activity as a protein kinase inhibitor, especially an FAK kinase inhibitor.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and relates to a class of novel pyrrolopyrimidine derivatives, pharmaceutically acceptable salts, hydrates, solvates or prodrugs of the derivatives, their preparation methods and their use as therapeutic agents, especially Use as a FAK inhibitor. Background technique [0002] As one of the largest protein superfamilies, protein kinases have numerous members and diverse functions. A total of 518 protein kinases have been found in the human genome, including typical kinases (478 types) and atypical kinases (40 types). Finding potential new targets for disease treatment based on kinase signaling pathway transduction has attracted extensive attention from pharmaceutical researchers, and using protein kinase inhibitors to regulate abnormal kinase activity in cells has also become an important strategy for the treatment of related diseases. More than forty protein kinase inhibitors have been successfull...

Claims

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Application Information

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IPC IPC(8): C07D487/04C07F9/6561A61P35/00A61K31/519A61K31/675
CPCA61P35/00C07D487/04C07F9/6561
Inventor 赵冬梅王瑞峰程卯生陈以轩赵相欣于思佳杨博文
Owner SHENYANG PHARMA UNIVERSITY
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