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2-amino pteridinone derivative or salt thereof as well as preparation method and application of 2-amino pteridinone derivative or salt thereof

An alkyl and aryl technology, applied in the field of 2-aminopteridone derivatives or their salts and their preparation, can solve the problems of low response rate of immunotherapy and the like

Pending Publication Date: 2022-04-05
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although immunotherapy has achieved some success in various types of cancer, there are multiple compensatory immunosuppressive mechanisms in the tumor microenvironment (TME), resulting in a low response rate to immunotherapy

Method used

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  • 2-amino pteridinone derivative or salt thereof as well as preparation method and application of 2-amino pteridinone derivative or salt thereof
  • 2-amino pteridinone derivative or salt thereof as well as preparation method and application of 2-amino pteridinone derivative or salt thereof
  • 2-amino pteridinone derivative or salt thereof as well as preparation method and application of 2-amino pteridinone derivative or salt thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0161] Embodiment one 2-Amino-8-(4-methoxybenzyl)-4-(5-methylfuran-2-yl)pteridin-7(8H)-one

[0162] (2-Amino-8-(4-methoxybenzyl)-4-(5-methylfuran-2-yl)pteridin-7(8H)-one)

[0163]

[0164] Step 1: 6-Chloro-N 4 Synthesis of -(4-methoxybenzyl)pyridine-2,4,5-triamine

[0165] 2,5-diamino-4,6-dichloropyrimidine (1.79g, 10.0mmol, 1.0equiv.), 4-methoxybenzylamine (2.06g, 15.0mmol, 1.5equiv.), Et 3 N (2.02 g, 20.0 mmol, 2.0 equiv.) was dissolved in an appropriate amount of Sec-BuOH, and stirred at 105° C. for 12 hours under nitrogen protection. TLC monitored the reaction in real time. After completion of the reaction, stand at 2-8°C until the solid precipitates, filter, wash with cold ethanol and petroleum ether successively, and dry to obtain a pink solid (2.0 g, yield: 71.5%).

[0166] ESI(m / z):[M+1] + 279.9; 1 H NMR (400MHz, DMSO-d 6 )δ7.25(d, J=8.4Hz, 2H), 6.94(s, 1H), 6.87(d, J=8.5Hz, 2H), 5.67(s, 2H), 4.47(s, 2H), 3.93( s,2H),3.71(s,3H).

[0167] Step 2: Synthesis ...

Embodiment 2

[0173] Embodiment two 2-Amino-8-(3-methoxybenzyl)-4-(5-methylfuran-2-yl)pteridin-7(8H)-one

[0174] (2-Amino-8-(3-methoxybenzyl)-4-(5-methylfuran-2-yl)pteridin-7(8H)-one)

[0175]

[0176] Route with reference to embodiment 1.

[0177] ESI(m / z):[M+1] + 363.8; 1 H NMR (400MHz, DMSO-d 6 )δ7.90(s,1H),7.77(d,J=3.5Hz,1H),7.52(brs,2H),7.21(t,J=7.9Hz,1H),6.97(s,1H),6.92( d,J=7.5Hz,1H),6.82(d,J=8.1Hz,1H),6.39(d,J=3.6Hz,1H),5.34(s,2H),3.72(s,3H),2.41( s,3H).

Embodiment 3

[0178] Embodiment three 2-Amino-8-(2-methoxybenzyl)-4-(5-methylfuran-2-yl)pteridin-7(8H)-one

[0179] (2-Amino-8-(2-methoxybenzyl)-4-(5-methylfuran-2-yl)pteridin-7(8H)-one)

[0180]

[0181] Route with reference to embodiment 1.

[0182] ESI(m / z):[M+1] + 363.8; 1 H NMR (400MHz, DMSO-d 6 )δ7.93(s,1H),7.81(d,J=3.4Hz,1H),7.56(brs,2H),7.21(d,J=8.0Hz,1H),7.02(d,J=8.2Hz, 1H), 6.78(t, J=7.3Hz, 1H), 6.58(d, J=7.6Hz, 1H), 6.41(s, 1H), 5.31(s, 2H), 3.87(s, 3H), 2.41( s,3H).

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Abstract

The invention belongs to the field of chemical medicines, and relates to a 2-amino pteridinone derivative or a salt thereof as well as a preparation method and application of the 2-amino pteridinone derivative. The compounds have a structure as shown in a formula (I), have adenosine A2A receptor (A2AR) inhibition activity, and can be used for preparing medicines for treating or preventing diseases related to A2AR.

Description

technical field [0001] The invention relates to the field of chemistry and medicine, and relates to a 2-aminopteridinone derivative or a salt thereof, a preparation method and application thereof. Background technique [0002] As an endogenous purine nucleoside, adenosine participates in many physiological and pathological processes: it is an essential precursor for the synthesis of adenosine triphosphate (ATP), the main molecule for storing cellular energy, and an important metabolic intermediate for the synthesis of nucleotides. Since 1983, four subtypes of adenosine receptors (A 1 、A 2A 、A 2B and A 3 ) was cloned, and extracellular adenosine plays a role by regulating these four types of receptors. Adenosine receptors belong to a class of G protein-coupled receptors (GPCRs) that are widely distributed in the body and play diverse roles, including: vasodilation and ischemia-reperfusion, angiogenesis, cardiac rhythm and circulation, sleep and arousal, neurodegeneration ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D475/00C07D519/00A61K31/525A61K31/551A61P35/00A61P25/16A61P21/00A61P25/28A61P9/10A61P19/02A61P1/16A61P25/18A61P25/00A61P31/04
Inventor 王永辉余发志祝晨宇谢琼
Owner FUDAN UNIV
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