EA022629B1 - Имидазопираны для применения в качестве ингибиторов киназ - Google Patents

Info

Publication number

EA022629B1

EA022629B1 EA201101497A EA201101497A EA022629B1 EA 022629 B1 EA022629 B1 EA 022629B1 EA 201101497 A EA201101497 A EA 201101497A EA 201101497 A EA201101497 A EA 201101497A EA 022629 B1 EA022629 B1 EA 022629B1

Authority

EA

Eurasian Patent Office

Prior art keywords

optionally substituted

substituents selected

alkyl

groups

compound

Prior art date

2009-04-16

Links

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• 150000005235 imidazopyrazines Chemical class 0.000 title description 13
• 229940043355 kinase inhibitor Drugs 0.000 title description 4
• 239000003757 phosphotransferase inhibitor Substances 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 304
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• 150000002148 esters Chemical class 0.000 claims abstract description 28
• 150000003839 salts Chemical class 0.000 claims abstract description 27
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• 201000011510 cancer Diseases 0.000 claims abstract description 22
• 239000012453 solvate Substances 0.000 claims abstract description 16
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• 230000002062 proliferating effect Effects 0.000 claims abstract description 9
• 125000001424 substituent group Chemical group 0.000 claims description 237
• 239000000203 mixture Substances 0.000 claims description 175
• -1 indolonyl Chemical group 0.000 claims description 125
• 125000000217 alkyl group Chemical group 0.000 claims description 120
• 229910052739 hydrogen Inorganic materials 0.000 claims description 103
• 229910052736 halogen Inorganic materials 0.000 claims description 101
• 150000002367 halogens Chemical group 0.000 claims description 101
• 239000001257 hydrogen Substances 0.000 claims description 92
• 238000006243 chemical reaction Methods 0.000 claims description 90
• 238000000034 method Methods 0.000 claims description 85
• 125000003118 aryl group Chemical group 0.000 claims description 77
• 125000001072 heteroaryl group Chemical group 0.000 claims description 70
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 69
• 229910052757 nitrogen Inorganic materials 0.000 claims description 63
• 229910052760 oxygen Inorganic materials 0.000 claims description 62
• 125000005842 heteroatom Chemical group 0.000 claims description 57
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 53
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 52
• 229910052799 carbon Inorganic materials 0.000 claims description 48
• 229910052700 potassium Inorganic materials 0.000 claims description 45
• 239000000460 chlorine Substances 0.000 claims description 41
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 39
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 36
• 125000004429 atom Chemical group 0.000 claims description 35
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
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• 229910052740 iodine Inorganic materials 0.000 claims description 31
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
• 125000004122 cyclic group Chemical group 0.000 claims description 30
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 29
• 125000001153 fluoro group Chemical group F* 0.000 claims description 29
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 27
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• 229910052794 bromium Inorganic materials 0.000 claims description 27
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• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 23
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• 125000000623 heterocyclic group Chemical group 0.000 claims description 17
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• 125000004432 carbon atom Chemical group C* 0.000 claims description 11
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• 125000005843 halogen group Chemical group 0.000 claims description 9
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
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• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 8
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• XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 claims description 6
• 125000005647 linker group Chemical group 0.000 claims description 6
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• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
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• 229940088597 hormone Drugs 0.000 claims description 2
• 230000001506 immunosuppresive effect Effects 0.000 claims description 2
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• 229960004072 thrombin Drugs 0.000 claims description 2
• 230000009385 viral infection Effects 0.000 claims description 2
• 150000002431 hydrogen Chemical group 0.000 claims 7
• 208000035473 Communicable disease Diseases 0.000 claims 1
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• 108091000080 Phosphotransferase Proteins 0.000 abstract description 26
• 102000020233 phosphotransferase Human genes 0.000 abstract description 26
• 108090000623 proteins and genes Proteins 0.000 abstract description 19
• 102000004169 proteins and genes Human genes 0.000 abstract description 18
• 150000002632 lipids Chemical class 0.000 abstract description 14
• 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 abstract description 3
• 102000013530 TOR Serine-Threonine Kinases Human genes 0.000 abstract description 3
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 527
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 167
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• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
• 230000000694 effects Effects 0.000 description 22
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 21
• 125000004193 piperazinyl group Chemical group 0.000 description 21
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