EA033633B1 - Антипролиферативные соединения и способы их применения - Google Patents

Info

Publication number

EA033633B1

EA033633B1 EA201790174A EA201790174A EA033633B1 EA 033633 B1 EA033633 B1 EA 033633B1 EA 201790174 A EA201790174 A EA 201790174A EA 201790174 A EA201790174 A EA 201790174A EA 033633 B1 EA033633 B1 EA 033633B1

Authority

EA

Eurasian Patent Office

Prior art keywords

methyl

oxoisoindolin

dioxopiperidin

alkyl

difluoro

Prior art date

2014-07-11

Links

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• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 434
• 238000000034 method Methods 0.000 title claims abstract description 129
• 230000001028 anti-proliverative effect Effects 0.000 title 1
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 164
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 119
• 201000011510 cancer Diseases 0.000 claims abstract description 97
• 208000032839 leukemia Diseases 0.000 claims abstract description 55
• 238000011282 treatment Methods 0.000 claims abstract description 47
• 125000000217 alkyl group Chemical group 0.000 claims description 273
• 239000000203 mixture Substances 0.000 claims description 201
• 150000003839 salts Chemical class 0.000 claims description 166
• -1 3-chloro-4-methylphenyl Chemical group 0.000 claims description 154
• 229910052736 halogen Inorganic materials 0.000 claims description 153
• 150000002367 halogens Chemical class 0.000 claims description 153
• 229910052739 hydrogen Inorganic materials 0.000 claims description 142
• 239000001257 hydrogen Substances 0.000 claims description 142
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 140
• 125000001424 substituent group Chemical group 0.000 claims description 122
• 150000002431 hydrogen Chemical class 0.000 claims description 89
• 125000002947 alkylene group Chemical group 0.000 claims description 57
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• 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 52
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 52
• 229910052757 nitrogen Inorganic materials 0.000 claims description 48
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 45
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 43
• 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims description 29
• 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims description 28
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
• 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims description 27
• 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 22
• 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 20
• 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 20
• 230000000306 recurrent effect Effects 0.000 claims description 18
• 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims description 11
• 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 11
• 125000004076 pyridyl group Chemical group 0.000 claims description 10
• 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims description 8
• 238000011443 conventional therapy Methods 0.000 claims description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• 125000003386 piperidinyl group Chemical group 0.000 claims description 5
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
• 125000005843 halogen group Chemical group 0.000 claims description 3
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 4
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 4
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 3
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 3
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
• AMQUQDRMUDITED-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(4-methoxyphenyl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC=C(C=C1)OC)(F)F)=O)=O)=O AMQUQDRMUDITED-UHFFFAOYSA-N 0.000 claims 2
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 1
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
• DHJTVBVPHLKVMI-UHFFFAOYSA-N 2-(3-chloro-4-propan-2-yloxyphenyl)-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound ClC=1C=C(C=CC=1OC(C)C)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F DHJTVBVPHLKVMI-UHFFFAOYSA-N 0.000 claims 1
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
• HWTTYVZOLNGISA-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(2-fluorophenyl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=C(C=CC=C1)F)(F)F)=O)=O)=O HWTTYVZOLNGISA-UHFFFAOYSA-N 0.000 claims 1
• YSIRDUGLLWZOOG-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(2-methyl-4-propan-2-yloxyphenyl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=C(C=C(C=C1)OC(C)C)C)(F)F)=O)=O)=O YSIRDUGLLWZOOG-UHFFFAOYSA-N 0.000 claims 1
• WUFZNZYZAXHCPN-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(2-propan-2-yloxyphenyl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=C(C=CC=C1)OC(C)C)(F)F)=O)=O)=O WUFZNZYZAXHCPN-UHFFFAOYSA-N 0.000 claims 1
• SOBWPOFPIRJNGF-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(3-fluoro-2-methylphenyl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=C(C(=CC=C1)F)C)(F)F)=O)=O)=O SOBWPOFPIRJNGF-UHFFFAOYSA-N 0.000 claims 1
• SBVXMVCDPWXTDN-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(3-fluorophenyl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC(=CC=C1)F)(F)F)=O)=O)=O SBVXMVCDPWXTDN-UHFFFAOYSA-N 0.000 claims 1
• QAXYIRJMJNSMJY-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(5-fluoropyridin-2-yl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=NC=C(C=C1)F)(F)F)=O)=O)=O QAXYIRJMJNSMJY-UHFFFAOYSA-N 0.000 claims 1
• JQBQFDRIJYALAO-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-[2-fluoro-4-(trifluoromethoxy)phenyl]acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=C(C=C(C=C1)OC(F)(F)F)F)(F)F)=O)=O)=O JQBQFDRIJYALAO-UHFFFAOYSA-N 0.000 claims 1
• LBHWADWDSWEHSU-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-[3-(trifluoromethyl)pyridin-2-yl]acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=NC=CC=C1C(F)(F)F)(F)F)=O)=O)=O LBHWADWDSWEHSU-UHFFFAOYSA-N 0.000 claims 1
• MWPYSDVUWHYHGA-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-[4-(trifluoromethylsulfanyl)phenyl]acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC=C(C=C1)SC(F)(F)F)(F)F)=O)=O)=O MWPYSDVUWHYHGA-UHFFFAOYSA-N 0.000 claims 1
• PSZTVISAVWNYGJ-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2-(3-ethoxypyridin-2-yl)-2,2-difluoroacetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(F)(F)C1=NC=CC=C1OCC)=O)=O)=O PSZTVISAVWNYGJ-UHFFFAOYSA-N 0.000 claims 1
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