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Deuterated phenylamino pyrimidine compound and drug composition containing the same

一种化合物、氘代的技术，应用在医药领域，能够解决毒副作用、耐药性等问题

Active Publication Date: 2014-08-06
SUZHOU ZELGEN BIOPHARML
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although targeted inhibition of different protein kinases is beneficial for the treatment of kinase-related diseases, it is still very challenging to find new druggable compounds that specifically inhibit certain protein kinases and have good oral bioavailability
In addition, some protein kinase inhibitors currently on the market have certain problems such as toxic side effects and drug resistance.

Method used

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  • Deuterated phenylamino pyrimidine compound and drug composition containing the same
  • Deuterated phenylamino pyrimidine compound and drug composition containing the same
  • Deuterated phenylamino pyrimidine compound and drug composition containing the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0103] Embodiment 1: Preparation of N-(cyanomethyl)-4-(2-(4-(d 8 -morpholine)phenylamino)pyrimidin-4-yl)benzamide (compound 9)

[0104]

[0105] 1. Preparation of 4-(4-nitrophenyl)(d 8 -morpholine) (Compound 3)

[0106] In the flask, add compound 4-chloronitrobenzene (3.53g, 22.4mmol), d 8- Morpholine (2.35g, 24.6mmol) and potassium carbonate (6.07g, 44mmol). Dimethylsulfoxide (40 mL) was added. After the addition, the temperature was raised to 100° C. and stirred for 16 hours. TLC detection (ethyl acetate / petroleum ether=1 / 10) showed that the reaction was complete. After cooling to room temperature, water (100 mL) was added to quench the reaction. Dichloromethane (100 mL) extracted twice. The organic layers were combined and washed successively with water and saturated brine. Dry over anhydrous sodium sulfate. Filter and concentrate the filtrate under vacuum with a rotary evaporator to obtain the crude product. Crystallization in a mixed solvent of ethyl acetate ...

Embodiment 2

[0115] Embodiment 2 prepares N-(cyano group (d 2 -Methyl))-4-(2-(4-(d 8 -morpholine)phenylamino)pyrimidin-4-yl)benzamide;

[0116]

[0117] By the method described in Example 1, the difference is: use 2-amino-2,2-d 2 -Acetonitrile hydrochloride is replaced by 2-aminoacetonitrile hydrochloride to obtain the target compound.

Embodiment 3

[0118] Embodiment 3 prepares N-(cyano group (d 2 -Methyl))-4-(2-(4-(2',2',6',6'-d 4 -morpholine)phenylamino)pyrimidin-4-yl)benzamide;

[0119]

[0120] By the method described in Example 1, the difference is: use 2-amino-2,2-d 2 -Acetonitrile hydrochloride replaces 2-aminoacetonitrile hydrochloride, 2,2,6,6-d 4 - Morpholine replaces d 8 -morpholine, thereby obtaining the target compound.

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PUM

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Abstract

The present invention relates to a deuterated phenylamino pyrimidine compound and a drug composition containing the deuterated phenylamino pyrimidine compound. Particularly the present invention discloses a deuterated phenylamino pyrimidine compound represented by a formula (I), and a drug composition containing the deuterated phenylamino pyrimidine compound, or a crystal form, a pharmaceutically acceptable salt, a hydrate or a solvate thereof. The compound can be used for treating and / or preventing JAK kinase-associated diseases such as myeloproliferative diseases, cancers, immunologic diseases and the like.

Description

technical field [0001] The invention belongs to the field of medicine. Specifically, the present invention relates to a novel deuterated phenylaminopyrimidine compound and a pharmaceutical composition containing the compound. Background technique [0002] JAK (januskinase) is a non-receptor tyrosine kinase family. Four members have been found, namely JAK1, JAK2, JAK3 and TYK1. Its structure does not contain SH2 and SH3, and its C-terminus has two connected kinase domains. The substrate of JAK is STAT, which is a signal transducer and a transcriptional activator. After being phosphorylated by JAK, STAT undergoes dimerization, and then passes through the nuclear membrane and enters the nucleus to regulate the expression of related genes. This signaling pathway is called JAK- STAT pathway, which plays a role in hematopoietic and immune cell communication. The currently known effective and specific inhibitors of the four JAK kinases can be used to treat diseases such as cancer...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/42A61K31/5377A61P35/00A61P7/00A61P29/00A61P37/02A61P31/12A61P9/00A61P3/00A61P35/02A61P19/02A61P19/06A61P11/06A61P11/00A61P11/02
CPCC07D239/42C07D413/12C07B59/002A61K31/5377A61P11/00A61P11/02A61P11/06A61P19/02A61P19/06A61P29/00A61P3/00A61P31/12A61P35/00A61P35/02A61P37/02A61P37/06A61P43/00A61P7/00A61P9/00A61K45/06
Inventor 吕彬华盛泽林
Owner SUZHOU ZELGEN BIOPHARML
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