EA032416B1 - Соединения триазолопиримидина и их применения - Google Patents

Info

Publication number

EA032416B1

EA032416B1 EA201791420A EA201791420A EA032416B1 EA 032416 B1 EA032416 B1 EA 032416B1 EA 201791420 A EA201791420 A EA 201791420A EA 201791420 A EA201791420 A EA 201791420A EA 032416 B1 EA032416 B1 EA 032416B1

Authority

EA

Eurasian Patent Office

Prior art keywords

methyl

triazolo

dihydrobenzofuran

pyrimidin

amine

Prior art date

2014-12-23

Links

• Espacenet
• Global Dossier
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• YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical class BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 489
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• 150000003839 salts Chemical class 0.000 claims abstract description 87
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• 208000035475 disorder Diseases 0.000 claims abstract description 39
• 230000001404 mediated effect Effects 0.000 claims abstract description 21
• -1 C 1 -C 4 alkoxy Chemical group 0.000 claims description 502
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 135
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 133
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 112
• 125000004565 2,3-dihydrobenzofuran-4-yl group Chemical group O1CCC2=C1C=CC=C2* 0.000 claims description 108
• 239000010802 sludge Substances 0.000 claims description 56
• 239000003814 drug Substances 0.000 claims description 52
• FVLAYJRLBLHIPV-UHFFFAOYSA-N pyrimidin-5-amine Chemical compound NC1=CN=CN=C1 FVLAYJRLBLHIPV-UHFFFAOYSA-N 0.000 claims description 50
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 49
• 229940124597 therapeutic agent Drugs 0.000 claims description 35
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 34
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
• 238000011282 treatment Methods 0.000 claims description 31
• 206010028980 Neoplasm Diseases 0.000 claims description 27
• 229910052739 hydrogen Inorganic materials 0.000 claims description 23
• 229910052736 halogen Inorganic materials 0.000 claims description 22
• 125000005842 heteroatom Chemical group 0.000 claims description 22
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• 101000971468 Homo sapiens Protein kinase C zeta type Proteins 0.000 claims description 21
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• 125000004432 carbon atom Chemical group C* 0.000 claims description 21
• 150000002367 halogens Chemical class 0.000 claims description 21
• HVOVXNWEZWMGLZ-UHFFFAOYSA-N [1,2,4]triazolo[4,3-c]pyrimidin-5-amine Chemical compound NC1=NC=CC=2N1C=NN2 HVOVXNWEZWMGLZ-UHFFFAOYSA-N 0.000 claims description 19
• 229910052799 carbon Inorganic materials 0.000 claims description 18
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 17
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 17
• 125000000217 alkyl group Chemical group 0.000 claims description 17
• 125000000623 heterocyclic group Chemical group 0.000 claims description 17
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• 229940127084 other anti-cancer agent Drugs 0.000 claims description 11
• IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims description 11
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 10
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• 125000005843 halogen group Chemical group 0.000 claims description 9
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 8
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• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 8
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• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
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• AGRIQBHIKABLPJ-UHFFFAOYSA-N 1-Pyrrolidinecarboxaldehyde Chemical compound O=CN1CCCC1 AGRIQBHIKABLPJ-UHFFFAOYSA-N 0.000 claims description 6
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• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 6
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• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 5
• 201000011549 stomach cancer Diseases 0.000 claims description 5
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
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• 206010060862 Prostate cancer Diseases 0.000 claims description 4
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• 201000010881 cervical cancer Diseases 0.000 claims description 4
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
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• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
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• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 3
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