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Pyrimidopyrimidone compound and application thereof

A compound, pyrimidinone technology, applied in the field of pyrimidopyrimidinone compounds, can solve the problems of poor pharmacokinetic properties and poor selectivity

Active Publication Date: 2019-06-04
JINAN UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, there is an urgent need for new types of compounds, especially compounds with novel backbones to solve the problems of poor selectivity and poor pharmacokinetic properties.

Method used

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  • Pyrimidopyrimidone compound and application thereof
  • Pyrimidopyrimidone compound and application thereof
  • Pyrimidopyrimidone compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0123] (S)-1-(1-propionylpyrrolidin-3-yl)-3-(2-chlorobenzene)-7-(3-methyl-4-(4-methylpiperazin-1-yl) Anilino)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (XQJ330081)

[0124](S)-3-(2-chlorophenyl)-7-((3-methyl-4-(4-methylpiperazin-1-yl)phenyl)amino)-1-(1-propionylpyrrolidin-3-yl)-3, 4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

[0125]

[0126] Step 1. (S)-4-(1-tert-butoxycarbonylpyrrolyl-3-amino)-2-methylmercaptopyrimidine-5-ethyl carbonate (2)

[0127] 4-Chloro-2-methylmercaptopyrimidine-5-ethyl carbonate (24.98g, 107.4mmol), (S)-1-tert-butoxycarbonyl-3-aminopyrrolidine (22.0g, 118.2mmol), K 2 CO 3 (29.64g, 214.8mmol) was dissolved in 50mL of anhydrous DMF, heated to 70°C under the protection of argon, and stirred overnight. After cooling to room temperature, 500 mL of ice water was added with stirring, and a large amount of solids precipitated out. Filter under reduced pressure and dry in vacuo to obtain 26.0 g of white oil (yield 74%).

[0128] MS(ESI)m / z383.2[M+...

Embodiment 2

[0155] (S)-1-(1-acetylpyrrolidin-3-yl)-3-(2-chlorobenzene)-7-(3-methyl-4-(4-methylpiperazin-1-yl) Anilino)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (XQJ280073)

[0156]

[0157] The synthesis method refers to Example 1. Yield: 82%.

[0158] 1 HNMR (400MHz, CDCl 3 )δ8.01(s,0.6H),7.99(s,0.4H),7.52-7.49(m,1H),7.37-7.32(m,5H),7.09(s,0.6H),7.02-7.01(m ,1.4H),5.61-5.56(m,1H),4.65-4.60(m,1H),4.51-4.46(m,1H),4.23-4.10(m,0.2H),4.10-4.03(m,0.8H ),3.98-3.91(m,1H),3.79-3.72(m,1H),3.52-3.40(m,1H),2.93-2.92(m,4H),2.79-2.75(m,1H),2.58-2.57 (m,4H),2.36(s,3H),2.30(s,3H),2.19-2.15(m,1H),2.02(s,3H).

[0159] HRMS (ESI) for C 30 h 35 ClN 8 o 2 [M+H] + ,Calcd:575.2644,Found:575.2648.

Embodiment 3

[0161] (S)-1-(1-(2-methylpropionyl)pyrrolidin-3-yl)-3-(2-chlorobenzene)-7-(3-methyl-4-(4-methylpiperene) Azin-1-yl)anilino)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (XQJ280083)

[0162]

[0163] The synthesis method refers to Example 1. Yield: 80%.

[0164] 1 HNMR (400MHz, CDCl 3 )δ8.02(s,0.6H),8.00(s,0.4H),7.52-7.49(m,1H),7.36-7.30(m,5H),7.07(s,0.6H),7.03-7.00(m ,1H),6.96(s,0.4H),5.61-5.54(m,1H),4.65-4.61(m,1H),4.60-4.48(m,1H),4.11-4.08(m,0.7H),3 ,97-3.91(m,1.3H),3.88-3.79(m,1H),3.57-3.45(m,0.4H),3.43-3.40(m,0.6H),2.93-2.91(m,4H),2.82 -2.74(m,1H),2.59-2.57(m,5H),2.36(s,3H),2.30(s,3H),2.20-2.16(m,1H),1.14-1.09(m,3H),1.08 -1.06(m,3H).

[0165] HRMS (ESI) for C 32 h 39 ClN 8 o 2 [M+H] + ,Calcd:603.2957,Found:603.2957.

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Abstract

The invention relates to a pyrimidopyrimidone compound with a structure shown as formula (I) or its pharmaceutically acceptable salt or stereoisomer or prodrug molecule and application thereof. The pyrimidopyrimidone compound, or its pharmaceutically acceptable salt, prodrug molecule and pharmaceutical composition can effectively inhibit the effects of CSF1R and other protein kinases, also can inhibit the proliferation, migration and invasion of various tumor cells, can be used for preparation of anti-cancer drugs, and also can be used for preparation of drugs treating tumors and other hyperproliferative diseases in human beings and other mammals.

Description

technical field [0001] The invention belongs to the field of chemical medicine, and in particular relates to pyrimidopyrimidinone compounds and applications thereof. Background technique [0002] The human immune system has the most important anti-cancer mechanism. On the one hand, it can remove foreign substances such as bacteria and viruses, and on the other hand, it can eliminate aging cells and mutated cells in the body (some mutated cells will become cancer cells). However, when the mutant cells lose the identity that can be recognized by the immune system, they can escape the immune attack and grow unrestrictedly to form tumors. Therefore, the decline of immune ability has become the main internal cause of tumor occurrence. However, it is remarkable that the study found that the "tumor self-healing phenomenon" can still be observed. For example, some patients with advanced tumors gradually shrink and disappear after fever induced by infection, cold, etc.; and resectio...

Claims

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Application Information

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IPC IPC(8): C07D487/04A61K31/519A61P35/00
Inventor 丁克寻秋菊丁健陆小云谢华张章耿美玉任小梅童林江
Owner JINAN UNIVERSITY
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