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3H-[1,2,3]triazolo[4,5-D]pyrimidine compounds, their use as MTOR kinase and PI3 kinase inhibitors, and their syntheses

A compound, C6-C14 technology, applied in the direction of drug combination, organic chemistry, organic active ingredients, etc.

Inactive Publication Date: 2011-04-13
WYETH LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0019] These three mTOR inhibitors have nonlinear, but reproducible pharmacokinetic profiles

Method used

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  • 3H-[1,2,3]triazolo[4,5-D]pyrimidine compounds, their use as MTOR kinase and PI3 kinase inhibitors, and their syntheses
  • 3H-[1,2,3]triazolo[4,5-D]pyrimidine compounds, their use as MTOR kinase and PI3 kinase inhibitors, and their syntheses
  • 3H-[1,2,3]triazolo[4,5-D]pyrimidine compounds, their use as MTOR kinase and PI3 kinase inhibitors, and their syntheses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0639] Preparation of 3-[3-(1-benzylpiperidin-4-yl)-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5 -yl]phenol. 3-[3-(1-Benzylpiperidin-4-yl)-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5- Base] phenol from 3-(1-benzyl-piperidin-4-yl)-5-chloro-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5- d] Pyrimidine (100 mg, 0.24 mmol) and 3-hydroxyphenylboronic acid (60 mg, 0.36 mmol), prepared according to method 2, to give the title product (70 mg, 61% yield). MS (ESI) m / z 472.

Embodiment 2

[0641] Preparation of 5-[3-(1-benzylpiperidin-4-yl)-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5 -yl]pyrimidin-2-amine. 1-benzylpiperidin-4-yl)-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-yl]pyrimidine-2- Amines from 3-(1-benzyl-piperidin-4-yl)-5-chloro-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d] Pyrimidine (100 mg, 0.24 mmol) and 2-aminopyrimidine-4-boronic acid (66 mg, 0.48 mmol), prepared according to Method 2, gave the title product (52 mg, 46% yield); MS (ESI) m / z 473.

Embodiment 3

[0643] Preparation of 5-[3-(1-benzylpiperidin-4-yl)-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5 -yl]pyridin-3-ol. 1-benzylpiperidin-4-yl)-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-yl]pyrimidine-2- Amines from 3-(1-benzyl-piperidin-4-yl)-5-chloro-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d] Pyrimidine (160mg, 0.38mmol) and 3-methoxymethoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolane-2- Base)-pyridine (151mg, 0.57mmol), prepared according to Method 2 to give intermediate 3-(1-benzyl-piperidin-4-yl)-5-(5-methoxymethoxy-pyridine- 3-yl)-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidine. 3-(1-benzyl-piperidin-4-yl)-5-(5-methoxymethoxy-pyridin-3-yl)-7-morpholin-4-yl-3H-[1, 2,3]Triazolo[4,5-d]pyrimidine was dissolved in concentrated HCl (1 mL) and methanol (4 mL) and added to reflux for 1 hour. The reaction mixture was cooled to 0 °C for 15 min and the title product was collected by filtration (56 mg, 44% yield); MS (ESI) m / z 473.

[0644] Preparation of ...

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Abstract

The invention relates to 3H-[1,2,3]triazolo[4,5-d]pyrimidine compounds of the Formula 1 or a pharmaceutically acceptable salt thereof, wherein the constituent variables are as defined herein, compositions comprising the compounds, and methods for making and using the compounds.

Description

technical field [0001] The present invention relates to 3H-[1,2,3]triazolo[4,5-d]pyrimidine compounds, compositions comprising 3H-[1,2,3]triazolo[4,5-d]pyrimidine compounds , methods of synthesizing these compounds, and methods of treating PI3K-associated diseases. The present invention also relates to methods of treating mTOR-associated diseases. Background technique [0002] Phosphatidylinositol (hereinafter abbreviated as "PI") is a kind of phospholipid in cell membrane. In recent years it has become clear that PI also plays an important role in intracellular signal transduction. It is well recognized in the art that PI(4,5) diphosphate (PI(4,5)P2 or PIP2) is degraded by phospholipase C to diacylglycerol and inositol triphosphate (1,4,5), respectively, to induce Activation of protein kinase C and intracellular calcium mobilization [M.J. Berridge et al., Nature, 312, 315 (1984); Y. Nishizuka, Science, 225, 1365 (1984)]. [0003] In the late 1980s, phosphatidylinositol-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/519A61P35/00C07D487/04
CPCC07D487/04A61P13/12A61P35/00A61P35/02A61P43/00
Inventor 克里斯托夫·M·登哈特阿拉纳帕卡姆·M·文卡特森埃弗伦·G·德洛斯桑托斯陈泽成奥斯瓦尔多·多斯桑托斯纳塔斯杰·布鲁伊杰曼斯阿里·扎斯克杰伦·C·维海詹塞米拉米斯·艾拉尔-卡洛斯蒂安
Owner WYETH LLC
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