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Compound for inhibiting activity of BTK and/or JAK3

A compound and solvate technology, applied in the field of compounds that inhibit BTK and/or JAK3 kinase activity, can solve problems such as immunodeficiency

Active Publication Date: 2015-01-28
BEIJING HANMI PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Loss of function of the JAK3 kinase leads to immunodeficiency in humans and mice

Method used

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  • Compound for inhibiting activity of BTK and/or JAK3
  • Compound for inhibiting activity of BTK and/or JAK3
  • Compound for inhibiting activity of BTK and/or JAK3

Examples

Experimental program
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preparation example Construction

[0405] Preparation of compounds of the present invention

[0406] The following reaction scheme exemplifies the preparation method of the compound of formula I of the present invention by taking compounds of formula Ia, formula Ib and formula Ic as examples.

[0407] It should be understood by those skilled in the art that in the following description, combinations of substituents are permissible only when such combination can result in a stable compound.

[0408] Those skilled in the art will also understand that in the methods described below, intermediate compound functional groups may need to be protected by an appropriate protecting group "PG". Such functional groups include hydroxyl, amino, mercapto and carboxylic acid. Suitable hydroxy protecting groups include trialkylsilyl or diarylalkylsilyl groups (eg tert-butyldimethylsilyl, tert-butyldiphenylsilyl or trimethylsilyl) , tetrahydropyranyl, benzyl, etc. Suitable protecting groups for amino, amidino and guanidino ...

Embodiment 1

[0466] N-(cis-4-((2-((1-methyl-1H-pyrazol-4-yl)amino)thiophene[3,2-d]pyrimidin-4-yl)amino)cyclohexyl)propene Preparation of amides

[0467]

[0468] Step 1: Preparation of tert-butyl cis-4-((2-chlorothien[3,2-d]pyrimidin-4-yl)amino)cyclohexylaminocarboxylate

[0469]

[0470] 2,4-Dichlorothieno[3,2-d]pyrimidine (678 mg, 3.31 mmol) and tert-butyl cis-4-aminocyclohexylaminocarboxylate (849 mg, 3.97 mmol) were dissolved in tetrahydrofuran (10 mL), N,N-Diisopropylethylamine (0.9 mL, 4.97 mmol) was added. The reaction solution was reacted at 70° C. overnight, and then concentrated. The residue was added to water (20 mL), extracted with ethyl acetate (20 mL*3). The organic phase was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and separated by silica gel column chromatography (eluent: n-hexane: ethyl acetate = 1:5) to obtain 1.07 g of a white solid. Yield: 84.7%. MS(ESI,m / z):[M+H] + :383.4; 1 H-NMR (300MHz, CDCl 3 )δ:7.74(d,1H,J=5.4Hz),7.35...

Embodiment 57

[0496] N-(cis-4-((2-((1-methyl-1H-pyrazol-4-yl)amino)furo[3,2-d]pyrimidin-4-yl)amino)cyclohexyl)propene Preparation of amides

[0497]

[0498] Step 1: cis-N 1 Preparation of -(2-chlorofuro[3,2-d]pyrimidin-4-yl)cyclohexyl-1,4-diamine

[0499]

[0500] Dissolve 2,4-dichlorofuro[3,2-d]pyrimidine (188mg, 1mmol) in dichloromethane (5mL), add dropwise to cis-1,4-cyclohexanediamine (456mg, 4.0mmol) solution in dichloromethane (10 mL). The reaction solution was stirred at room temperature overnight, then concentrated. The residue was added to water (20 mL), extracted with ethyl acetate (20 mL*3). The organic phase was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and separated by silica gel column chromatography (eluent: n-hexane: ethyl acetate = 1:1) to obtain 140 mg of a light yellow solid. Yield: 52.6%. MS(ESI,m / z):[M+H] + :267.1; 1 H-NMR (300MHz, CD 3 OD):8.01-8.00(d,1H,J=2.1Hz),6.78-6.77(d,1H,J=2.1Hz),4.24-2.22(m,1H),3.07-3.03(m,1H),1.9...

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Abstract

The invention relates to a compound for inhibiting the activity of BTK (Bruton's Tyrosine Kinase) and / or JAK3 (Janus Tyrosine Kinase 3), a medicinal composition of the compound, a use of the compound in the pharmacy, a method for inhibiting the activity of BTK and / or JAK3 by using the compound, and a method for treating and / or preventing BTK and / or JAK3 mediated diseases or illnesses in mammals (especially human beings) by using the compound. The compound is represented by structural formula I shown in the specification.

Description

technical field [0001] The present invention relates to compounds that inhibit BTK (Bruton's tyrosine kinase) and / or JAK3 (Janus tyrosine kinase 3) kinase activity, their pharmaceutical compositions, their use in pharmacy, and their use to inhibit BTK and / or Methods of JAK3 activity and methods of using same to treat and / or prevent BTK and / or JAK3 mediated diseases or conditions in mammals, especially humans. Background technique [0002] Protein kinases constitute one of the largest families of human enzymes, with more than 500 species identified in humans so far. They modulate complex signaling pathways by transferring phosphate groups to proteins to regulate the activity of specific proteins. Aberrant protein kinase activity is associated with a variety of diseases, from cancer to autoimmune diseases. In view of the key role of protein kinases in signal transduction pathways and the correlation between kinase activity and various diseases, kinase inhibitors have become ...

Claims

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Application Information

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IPC IPC(8): C07D495/04C07D487/04C07D519/00C07D491/048A61K31/519A61K31/5377A61K31/53A61P37/02A61P29/00A61P19/02A61P11/00A61P17/06A61P1/00A61P1/04A61P35/00A61P35/02
CPCC07D487/04C07D491/048C07D495/04C07D519/00A61K31/519A61K31/53A61K31/5377A61K45/06A61P1/00A61P1/04A61P11/00A61P17/00A61P17/06A61P19/00A61P19/02A61P25/00A61P29/00A61P35/00A61P35/02A61P37/02A61P37/06A61P43/00A61P7/02A61K2300/00C07D403/12C07D403/10C07D471/04
Inventor 刘金明车美英李功李占梅邱红娟金孟燮
Owner BEIJING HANMI PHARMA CO LTD
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