C-Myc protein inhibitor as well as preparation method and application thereof

A solvent compound, C1-C3 technology, applied in the field of medicine, can solve problems such as c-Myc inhibitors that have not been reported, and achieve excellent c-Myc protein inhibitory effect, simple synthesis method, and exact inhibitory effect.

Pending Publication Date: 2022-05-06
SUZHOU KINTOR PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] At present, many studies have confirmed the clinical development prospect of c-M

Method used

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  • C-Myc protein inhibitor as well as preparation method and application thereof
  • C-Myc protein inhibitor as well as preparation method and application thereof
  • C-Myc protein inhibitor as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0092] Synthesis of Compound A1

[0093] Compound A1:

[0094]

[0095]

[0096] Compounds A1-1 (156mg, 0.5mmol) and A1-2 (227mg, 0.6mmol) were dissolved in DCM (3mL), HATU (285mg, 0.75mmol) and TEA (151mg, 1.5mmol) were added and reacted at room temperature for two hours . Water was added, extracted with DCM (15mL*3), the organic phases were combined, the solvent was pulled dry, and the crude product was purified by medium pressure preparation to obtain compound A1 (28mg, yield 10%) as a white solid.

[0097] 1 H NMR (400MHz, DMSO) δ9.28 (s, 1H), 7.90 (d, J = 7.5Hz, 2H), 7.68 (d, J = 7.3Hz, 2H), 7.49–7.37 (m, 2H), 7.34 (t,J=7.2Hz,3H),4.30(dd,J=12.2,6.6Hz,2H),4.22(t,J=6.8Hz,1H),4.00(d,J=6.8Hz,1H),3.21 (dd,J=13.2,6.8Hz,2H),2.46–2.39(m,2H),2.17(dd,J=12.2,10.1Hz,1H),2.01(dd,J=14.6,6.9Hz,2H), 1.85–1.75(m,2H),1.74–1.65(m,1H),1.61(d,J=14.1Hz,1H),1.36(dd,J=12.7,10.3Hz,1H),1.25(dd,J= 19.3,15.2Hz,8H),0.91–0.75(m,9H).

[0098] Compounds A2-A19, 28-41, 44-55, 57-58, 66-69, 9...

Embodiment 2

[0271] Synthesis of compound A72

[0272] Compound A72:

[0273]

[0274] Synthesis of compound A72-2

[0275] Compound A72-1 (150mg, 0.617mmol) was dissolved in a mixed solvent (2mL) of toluene / methanol=1 / 3, and TMSCHN2 (2mL, 0.6M, 1.23mmol) was added under stirring at room temperature, and the reaction solution was light yellow and clear After stirring at room temperature for 5 min, TLC showed that the reaction was complete. The reaction solution was spin-dried, and dichloromethane (3 mL) and trifluoroacetic acid (1 mL) were added. After stirring at room temperature for 1 h, the reaction was complete, and the solvent was spin-dried to obtain the crude compound A72-2 ( 250mg, crude product).

[0276] Synthesis of compound A72-4

[0277] Compound A72-2 (250 mg, crude product), compound A72-3 (120 mg, 0.53 mmol) and HATU (243 mg, 0.63 mmol) were dissolved in dichloromethane (8 mL), and triethylamine (235 uL, 1.7 mmol), after stirring at room temperature for 2 hours, TLC ...

Embodiment 3

[0343] Embodiment 3: the synthesis of compound A91

[0344] Compound A91

[0345]

[0346] Compounds A91-1 (176mg, 0.5mmol) and A91-2 (202mg, 0.6mmol) were dissolved in DCM (3mL), HATU (285mg, 0.75mmol) and TEA (151mg, 1.5mmol) were added and reacted at room temperature for two hours . Add water, extract with DCM (15mL*3), combine the organic phases, pull dry the solvent, prepare and purify the crude product with medium pressure to obtain white solid compound A91 (17mg, yield 6%)

[0347] 1H NMR (400MHz, DMSO) δ9.48 (d, J = 10.6Hz, 1H), 7.89 (d, J = 7.5Hz, 2H), 7.72–7.63 (m, 2H), 7.44–7.25 (m, 5H) ,4.25(dt,J=17.6,5.2Hz,3H),3.94(t,J=6.9Hz,1H),3.23(dd,J=15.5,8.5Hz,1H),2.39(d,J=7.3Hz, 1H),2.20–2.09(m,1H),1.98(d,J=21.6Hz,1H),1.77(dd,J=11.0,5.4Hz,2H),1.58(d,J=13.5Hz,1H), 1.39–1.32(m,1H),1.21(t,J=7.8Hz,8H),0.98(dd,J=7.0,4.1Hz,3H),0.86(t,J=10.8Hz,1H),0.78(s ,3H),0.42–0.27(m,2H),0.22(d,J=3.5Hz,2H).

[0348] The synthetic method of compound 92 is the same as that of A91.

[...

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Abstract

The invention relates to a c-Myc protein inhibitor as well as a preparation method and application thereof, the c-Myc protein inhibitor can selectively inhibit c-Myc protein, so that the c-Myc protein inhibitor can be used for preventing and treating c-Myc protein disorder related diseases, such as cancer, cardiovascular and cerebrovascular diseases, virus infection related diseases and the like.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to a c-Myc protein inhibitor and its preparation method and application. Background technique [0002] Oncogenes refer to genes that exist in the genome of cells or viruses, and whose encoded products can transform normal cells to form tumors. When such genes are in a normal state, they are proto-oncogenes. The study found that proto-oncogenes widely exist in the biological world, and have many important functions such as maintaining normal physiological functions, regulating cell growth and differentiation, including ras family, myc family, myb family, src family, sis family and so on. When affected by physical, chemical, microbial and other factors, proto-oncogenes can be mutated, amplified, activated, and transformed into oncogenes, and oncogene-encoded products can induce tumors in animals. [0003] The human c-Myc proto-oncogene is located on human chromosome 8q24 and conta...

Claims

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Application Information

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IPC IPC(8): C07F5/02A61K31/69A61P35/00A61P9/00A61P31/18A61P31/20A61P31/14A61P31/16A61P31/12
CPCC07F5/02A61P35/00A61P9/00A61P31/18A61P31/20A61P31/14A61P31/16A61P31/12A61K31/69A61P43/00A61K31/16Y02A50/30
Inventor 童友之许若陈洁来鲁华
Owner SUZHOU KINTOR PHARMA
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