AU2015287688B2 - Antiproliferative compounds and methods of use thereof - Google Patents

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Publication number

AU2015287688B2

AU2015287688B2 AU2015287688A AU2015287688A AU2015287688B2 AU 2015287688 B2 AU2015287688 B2 AU 2015287688B2 AU 2015287688 A AU2015287688 A AU 2015287688A AU 2015287688 A AU2015287688 A AU 2015287688A AU 2015287688 B2 AU2015287688 B2 AU 2015287688B2

Authority

AU

Australia

Prior art keywords

methyl

dioxopiperidin

oxoisoindolin

difluoro

acetamide

Prior art date

2014-07-11

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 449
• 238000000034 method Methods 0.000 title claims abstract description 162
• 230000001028 anti-proliverative effect Effects 0.000 title description 2
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 159
• 201000011510 cancer Diseases 0.000 claims abstract description 90
• 208000032839 leukemia Diseases 0.000 claims abstract description 54
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 29
• 239000003795 chemical substances by application Substances 0.000 claims abstract description 16
• 125000000217 alkyl group Chemical group 0.000 claims description 342
• 125000001188 haloalkyl group Chemical group 0.000 claims description 247
• 125000005843 halogen group Chemical group 0.000 claims description 192
• 229910052739 hydrogen Inorganic materials 0.000 claims description 176
• 239000001257 hydrogen Substances 0.000 claims description 176
• 239000000203 mixture Substances 0.000 claims description 175
• 150000003839 salts Chemical class 0.000 claims description 154
• 239000012453 solvate Substances 0.000 claims description 150
• 125000001424 substituent group Chemical group 0.000 claims description 150
• 125000000623 heterocyclic group Chemical group 0.000 claims description 148
• 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 144
• 125000001072 heteroaryl group Chemical group 0.000 claims description 134
• 239000013078 crystal Substances 0.000 claims description 133
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 112
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 109
• 125000003545 alkoxy group Chemical group 0.000 claims description 95
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 87
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 86
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 82
• 125000003107 substituted aryl group Chemical group 0.000 claims description 78
• 125000002947 alkylene group Chemical group 0.000 claims description 70
• 125000003118 aryl group Chemical group 0.000 claims description 60
• 125000004450 alkenylene group Chemical group 0.000 claims description 57
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 56
• 125000004043 oxo group Chemical group O=* 0.000 claims description 56
• 229910052757 nitrogen Inorganic materials 0.000 claims description 55
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 54
• 229910052760 oxygen Inorganic materials 0.000 claims description 54
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 52
• 229910052717 sulfur Inorganic materials 0.000 claims description 52
• 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 50
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 49
• -1 chloro, methyl Chemical group 0.000 claims description 44
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 40
• 239000013543 active substance Substances 0.000 claims description 32
• 238000002560 therapeutic procedure Methods 0.000 claims description 31
• 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims description 28
• 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims description 27
• 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims description 26
• 239000002246 antineoplastic agent Substances 0.000 claims description 23
• 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
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
• 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims description 11
• 102000004127 Cytokines Human genes 0.000 claims description 11
• 108090000695 Cytokines Proteins 0.000 claims description 11
• 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 10
• 238000011443 conventional therapy Methods 0.000 claims description 10
• 230000001225 therapeutic effect Effects 0.000 claims description 9
• 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims description 8
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
• 125000001153 fluoro group Chemical group F* 0.000 claims description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• 239000002904 solvent Substances 0.000 claims description 7
• 241000124008 Mammalia Species 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([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
• 239000002253 acid Substances 0.000 claims description 4
• 239000000427 antigen Substances 0.000 claims description 4
• 229940111134 coxibs Drugs 0.000 claims description 4
• 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims description 4
• 102000036639 antigens Human genes 0.000 claims description 3
• 108091007433 antigens Proteins 0.000 claims description 3
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
• 230000002519 immonomodulatory effect Effects 0.000 claims description 3
• 239000003018 immunosuppressive agent Substances 0.000 claims description 3
• 229940125721 immunosuppressive agent Drugs 0.000 claims description 3
• 230000009467 reduction Effects 0.000 claims description 3
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 30
• ZLIBRCVWTYTMME-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound ClC1=C(C=CC=C1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F ZLIBRCVWTYTMME-UHFFFAOYSA-N 0.000 claims 7
• XLONUSFDGBQNQO-UHFFFAOYSA-N 2-(3-chlorophenyl)-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound ClC=1C=C(C=CC=1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F XLONUSFDGBQNQO-UHFFFAOYSA-N 0.000 claims 7
• DOCFCULFTLNCRC-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(4-fluorophenyl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC=C(C=C1)F)(F)F)=O)=O)=O DOCFCULFTLNCRC-UHFFFAOYSA-N 0.000 claims 7
• 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 7
• METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 7
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 4
• NCGYEIAZOMELDK-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound ClC1=C(C=CC(=C1)Cl)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F NCGYEIAZOMELDK-UHFFFAOYSA-N 0.000 claims 3
• QQONSQRPXGBPLY-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound FC1=C(C=CC(=C1)F)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F QQONSQRPXGBPLY-UHFFFAOYSA-N 0.000 claims 3
• PJGSJRDAOLRPTF-UHFFFAOYSA-N 2-(2,6-difluorophenyl)-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound FC1=C(C(=CC=C1)F)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F PJGSJRDAOLRPTF-UHFFFAOYSA-N 0.000 claims 3
• AIHKQMOGDSBXOL-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound NC1=NC=CC(=N1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F AIHKQMOGDSBXOL-UHFFFAOYSA-N 0.000 claims 3
• DQBFRGQHCCHNSG-UHFFFAOYSA-N 2-(2-aminopyrimidin-5-yl)-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound NC1=NC=C(C=N1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F DQBFRGQHCCHNSG-UHFFFAOYSA-N 0.000 claims 3
• ZHBWCLQDPRTPKV-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound FC=1C=C(C=CC=1F)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F ZHBWCLQDPRTPKV-UHFFFAOYSA-N 0.000 claims 3
• AMUVSIVTAOXJLA-UHFFFAOYSA-N 2-(3-chloro-2-methylphenyl)-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound ClC=1C(=C(C=CC=1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F)C AMUVSIVTAOXJLA-UHFFFAOYSA-N 0.000 claims 3
• DDMLCIFNORUQRL-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound ClC=1C=C(C=CC=1F)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F DDMLCIFNORUQRL-UHFFFAOYSA-N 0.000 claims 3
• JFNYNFDROJUTRW-UHFFFAOYSA-N 2-(3-chloro-4-methoxyphenyl)-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(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F JFNYNFDROJUTRW-UHFFFAOYSA-N 0.000 claims 3
• 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 3
• UXOHQYKAUVRSGR-UHFFFAOYSA-N 2-(4-bromophenyl)-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound BrC1=CC=C(C=C1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F UXOHQYKAUVRSGR-UHFFFAOYSA-N 0.000 claims 3
• SLEUIEVUCBQKRN-UHFFFAOYSA-N 2-(4-chloro-2-fluorophenyl)-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound ClC1=CC(=C(C=C1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F)F SLEUIEVUCBQKRN-UHFFFAOYSA-N 0.000 claims 3
• BEUXWCQJDJUWKP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenyl)-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound ClC1=CC(=C(C=C1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F)C BEUXWCQJDJUWKP-UHFFFAOYSA-N 0.000 claims 3
• KZCJVXJRANKAGX-UHFFFAOYSA-N 2-(4-chloro-3-fluorophenyl)-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound ClC1=C(C=C(C=C1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F)F KZCJVXJRANKAGX-UHFFFAOYSA-N 0.000 claims 3
• PWBHUSLMHZLGRN-UHFFFAOYSA-N 2-(4-chlorophenyl)-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound ClC1=CC=C(C=C1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F PWBHUSLMHZLGRN-UHFFFAOYSA-N 0.000 claims 3
• XXOZRQAXDWOASO-UHFFFAOYSA-N 2-(4-cyclopropylphenyl)-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound C1(CC1)C1=CC=C(C=C1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F XXOZRQAXDWOASO-UHFFFAOYSA-N 0.000 claims 3
• PBXOPAYJJVDLNM-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F PBXOPAYJJVDLNM-UHFFFAOYSA-N 0.000 claims 3
• KHOFGXWGIVOQDL-UHFFFAOYSA-N 2-(5-bromopyridin-2-yl)-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound BrC=1C=CC(=NC=1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F KHOFGXWGIVOQDL-UHFFFAOYSA-N 0.000 claims 3
• IFHGNGPDPXZMPD-UHFFFAOYSA-N 2-(5-chloropyridin-2-yl)-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound ClC=1C=CC(=NC=1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F IFHGNGPDPXZMPD-UHFFFAOYSA-N 0.000 claims 3
• BLUVQMUHGZOMQM-UHFFFAOYSA-N 2-(5-cyclopropylpyridin-2-yl)-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound C1(CC1)C=1C=CC(=NC=1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F BLUVQMUHGZOMQM-UHFFFAOYSA-N 0.000 claims 3
• GMHBAETVCYHAFR-UHFFFAOYSA-N 2-(5-tert-butylpyridin-2-yl)-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound C(C)(C)(C)C=1C=CC(=NC=1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F GMHBAETVCYHAFR-UHFFFAOYSA-N 0.000 claims 3
• IIEPAZNFJBYJHI-UHFFFAOYSA-N 2-[3-(dimethylamino)phenyl]-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound CN(C=1C=C(C=CC=1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F)C IIEPAZNFJBYJHI-UHFFFAOYSA-N 0.000 claims 3
• VZXULRDQFRXODC-UHFFFAOYSA-N 2-[3-[2-(dimethylamino)ethoxy]phenyl]-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound CN(CCOC=1C=C(C=CC=1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F)C VZXULRDQFRXODC-UHFFFAOYSA-N 0.000 claims 3
• FAAWXONVJKBBDX-UHFFFAOYSA-N 2-[3-bromo-4-(trifluoromethoxy)phenyl]-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound BrC=1C=C(C=CC=1OC(F)(F)F)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F FAAWXONVJKBBDX-UHFFFAOYSA-N 0.000 claims 3
• JTODFZWZPZGMBU-UHFFFAOYSA-N 2-[4-chloro-2-(trifluoromethoxy)phenyl]-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound ClC1=CC(=C(C=C1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F)OC(F)(F)F JTODFZWZPZGMBU-UHFFFAOYSA-N 0.000 claims 3
• MZMQDTGOAVTIRS-UHFFFAOYSA-N 2-[4-chloro-2-(trifluoromethyl)phenyl]-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound ClC1=CC(=C(C=C1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F)C(F)(F)F MZMQDTGOAVTIRS-UHFFFAOYSA-N 0.000 claims 3
• WPBYBHMGNDQPDI-UHFFFAOYSA-N 2-cyclohexyl-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound C1(CCCCC1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F WPBYBHMGNDQPDI-UHFFFAOYSA-N 0.000 claims 3
• SQMHSDLOEJOJIL-UHFFFAOYSA-N 2-cyclopentyl-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound C1(CCCC1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F SQMHSDLOEJOJIL-UHFFFAOYSA-N 0.000 claims 3
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 3
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
• JCBZZKRPJCCDMM-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(1-methyl-6-oxopyridazin-4-yl)acetamide Chemical compound CN1N=CC(=CC1=O)C(F)(F)C(=O)NCC1=CC2=C(C=C1)C(=O)N(C2)C1CCC(=O)NC1=O JCBZZKRPJCCDMM-UHFFFAOYSA-N 0.000 claims 3
• VZKNLAMLJWIKET-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(2-fluoro-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)F)(F)F)=O)=O)=O VZKNLAMLJWIKET-UHFFFAOYSA-N 0.000 claims 3
• 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 3
• LYPGTEQCLOXQCX-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(2-methoxyphenyl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=C(C=CC=C1)OC)(F)F)=O)=O)=O LYPGTEQCLOXQCX-UHFFFAOYSA-N 0.000 claims 3
• 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 3
• HEHFPFWQZAJOPM-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(2-methylphenyl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=C(C=CC=C1)C)(F)F)=O)=O)=O HEHFPFWQZAJOPM-UHFFFAOYSA-N 0.000 claims 3
• 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 3
• 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 3
• NUFAWRNBHUWJFG-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(3-fluoro-4-propan-2-yloxyphenyl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC(=C(C=C1)OC(C)C)F)(F)F)=O)=O)=O NUFAWRNBHUWJFG-UHFFFAOYSA-N 0.000 claims 3
• 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 3
• BFORLTWCVIRSQY-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(3-methyl-4-propan-2-yloxyphenyl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC(=C(C=C1)OC(C)C)C)(F)F)=O)=O)=O BFORLTWCVIRSQY-UHFFFAOYSA-N 0.000 claims 3
• OKPHSMZSHNDXNN-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(3-methylphenyl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C=1C=C(C=CC=1)C)(F)F)=O)=O)=O OKPHSMZSHNDXNN-UHFFFAOYSA-N 0.000 claims 3
• FLHSVDCZBFBMDD-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(3-methylpyridin-2-yl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=NC=CC=C1C)(F)F)=O)=O)=O FLHSVDCZBFBMDD-UHFFFAOYSA-N 0.000 claims 3
• SKXBLDSEPZGVHM-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(3-methylsulfonylphenyl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC(=CC=C1)S(=O)(=O)C)(F)F)=O)=O)=O SKXBLDSEPZGVHM-UHFFFAOYSA-N 0.000 claims 3
• UOCBVEPOXDRRCU-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(3-morpholin-4-ylphenyl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC(=CC=C1)N1CCOCC1)(F)F)=O)=O)=O UOCBVEPOXDRRCU-UHFFFAOYSA-N 0.000 claims 3
• LEKLBINUIFRTJO-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(4-fluoro-2-methylphenyl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=C(C=C(C=C1)F)C)(F)F)=O)=O)=O LEKLBINUIFRTJO-UHFFFAOYSA-N 0.000 claims 3
• PSIXNTKRSHRNNV-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(4-fluoro-2-propan-2-yloxyphenyl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=C(C=C(C=C1)F)OC(C)C)(F)F)=O)=O)=O PSIXNTKRSHRNNV-UHFFFAOYSA-N 0.000 claims 3
• PWANIHFJALMGQE-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(4-fluorocyclohexyl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1CCC(CC1)F)(F)F)=O)=O)=O PWANIHFJALMGQE-UHFFFAOYSA-N 0.000 claims 3
• YNEFVZUMWDLSFV-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(4-methylsulfonylphenyl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC=C(C=C1)S(=O)(=O)C)(F)F)=O)=O)=O YNEFVZUMWDLSFV-UHFFFAOYSA-N 0.000 claims 3
• ZZKILESADYZFJV-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(4-propan-2-yloxyphenyl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC=C(C=C1)OC(C)C)(F)F)=O)=O)=O ZZKILESADYZFJV-UHFFFAOYSA-N 0.000 claims 3
• RYKJGMYMKGWRQA-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(4-propan-2-ylphenyl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC=C(C=C1)C(C)C)(F)F)=O)=O)=O RYKJGMYMKGWRQA-UHFFFAOYSA-N 0.000 claims 3
• 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 3
• QAENVAZAYPDROH-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(5-methoxypyridin-2-yl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=NC=C(C=C1)OC)(F)F)=O)=O)=O QAENVAZAYPDROH-UHFFFAOYSA-N 0.000 claims 3
• GRFBTHLLUKYPJX-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(5-methylpyridin-2-yl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=NC=C(C=C1)C)(F)F)=O)=O)=O GRFBTHLLUKYPJX-UHFFFAOYSA-N 0.000 claims 3
• PRTMHZHJOHIYDF-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(5-propan-2-yloxypyridin-2-yl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=NC=C(C=C1)OC(C)C)(F)F)=O)=O)=O PRTMHZHJOHIYDF-UHFFFAOYSA-N 0.000 claims 3
• HEVKLJWTQBESTQ-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(5-propan-2-ylpyridin-2-yl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=NC=C(C=C1)C(C)C)(F)F)=O)=O)=O HEVKLJWTQBESTQ-UHFFFAOYSA-N 0.000 claims 3
• OLNJAELCYXWFIQ-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-[2-(2,2,2-trifluoroethoxy)phenyl]acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=C(C=CC=C1)OCC(F)(F)F)(F)F)=O)=O)=O OLNJAELCYXWFIQ-UHFFFAOYSA-N 0.000 claims 3
• TUTCXLAAKLEFBL-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-[2-(2-methoxyethoxy)phenyl]acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=C(C=CC=C1)OCCOC)(F)F)=O)=O)=O TUTCXLAAKLEFBL-UHFFFAOYSA-N 0.000 claims 3
• DUJSYJNRJSCIBC-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-[2-(trifluoromethoxy)phenyl]acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=C(C=CC=C1)OC(F)(F)F)(F)F)=O)=O)=O DUJSYJNRJSCIBC-UHFFFAOYSA-N 0.000 claims 3
• 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 3
• RKIADEYYBGBGDM-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-[2-methyl-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)C)(F)F)=O)=O)=O RKIADEYYBGBGDM-UHFFFAOYSA-N 0.000 claims 3
• NBCDJJHARBDWLT-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-[3-(2-hydroxyethoxy)phenyl]acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC(=CC=C1)OCCO)(F)F)=O)=O)=O NBCDJJHARBDWLT-UHFFFAOYSA-N 0.000 claims 3
• IQVGIYKIPNVLDX-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-[3-(2-hydroxyethyl)phenyl]acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC(=CC=C1)CCO)(F)F)=O)=O)=O IQVGIYKIPNVLDX-UHFFFAOYSA-N 0.000 claims 3
• RJQYMGWMQORYNG-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-[3-(2-methoxyethoxy)phenyl]acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC(=CC=C1)OCCOC)(F)F)=O)=O)=O RJQYMGWMQORYNG-UHFFFAOYSA-N 0.000 claims 3
• YVTXDRLLWAJHRM-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-[3-(2-methylsulfonylethoxy)phenyl]acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC(=CC=C1)OCCS(=O)(=O)C)(F)F)=O)=O)=O YVTXDRLLWAJHRM-UHFFFAOYSA-N 0.000 claims 3
• MYEINJFBFWZVCU-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-[3-(2-morpholin-4-ylethoxy)phenyl]acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC(=CC=C1)OCCN1CCOCC1)(F)F)=O)=O)=O MYEINJFBFWZVCU-UHFFFAOYSA-N 0.000 claims 3
• GRWHSPLWEFAOFL-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-[3-(3-methylsulfonylpropyl)phenyl]acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC(=CC=C1)CCCS(=O)(=O)C)(F)F)=O)=O)=O GRWHSPLWEFAOFL-UHFFFAOYSA-N 0.000 claims 3
• HKQUNDIITVPWEA-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-[3-(morpholin-4-ylmethyl)phenyl]acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC(=CC=C1)CN1CCOCC1)(F)F)=O)=O)=O HKQUNDIITVPWEA-UHFFFAOYSA-N 0.000 claims 3
• 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 3
• KKTJMTHRCJXXOJ-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-[3-[2-(2-methoxyethoxy)ethoxy]phenyl]acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC(=CC=C1)OCCOCCOC)(F)F)=O)=O)=O KKTJMTHRCJXXOJ-UHFFFAOYSA-N 0.000 claims 3
• WQQIAMDXCBPBBB-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-[3-[2-(methylamino)ethoxy]phenyl]acetamide Chemical compound CNCCOC1=CC=CC(=C1)C(F)(F)C(=O)NCC1=CC2=C(C=C1)C(=O)N(C2)C1CCC(=O)NC1=O WQQIAMDXCBPBBB-UHFFFAOYSA-N 0.000 claims 3
• KQDJCLOQMKMRBG-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-[3-methyl-4-(trifluoromethoxy)phenyl]acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC(=C(C=C1)OC(F)(F)F)C)(F)F)=O)=O)=O KQDJCLOQMKMRBG-UHFFFAOYSA-N 0.000 claims 3
• VSEXZUHNKMCCHH-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-[4-(2-fluoropropan-2-yl)phenyl]acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC=C(C=C1)C(C)(C)F)(F)F)=O)=O)=O VSEXZUHNKMCCHH-UHFFFAOYSA-N 0.000 claims 3
• IDTPIHJNADCWNA-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-[4-(2-methoxyethoxy)phenyl]acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC=C(C=C1)OCCOC)(F)F)=O)=O)=O IDTPIHJNADCWNA-UHFFFAOYSA-N 0.000 claims 3
• 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 3
• FAHBFJBZVMRZPX-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-[4-fluoro-2-(2,2,2-trifluoroethoxy)phenyl]acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=C(C=C(C=C1)F)OCC(F)(F)F)(F)F)=O)=O)=O FAHBFJBZVMRZPX-UHFFFAOYSA-N 0.000 claims 3
• ZKWXXNYCHCSAHB-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-[4-fluoro-2-(trifluoromethoxy)phenyl]acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=C(C=C(C=C1)F)OC(F)(F)F)(F)F)=O)=O)=O ZKWXXNYCHCSAHB-UHFFFAOYSA-N 0.000 claims 3
• NCEREZDHAKLJND-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-[4-fluoro-2-(trifluoromethyl)phenyl]acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=C(C=C(C=C1)F)C(F)(F)F)(F)F)=O)=O)=O NCEREZDHAKLJND-UHFFFAOYSA-N 0.000 claims 3
• GVBWAGDULNKFNC-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-[4-methyl-2-(trifluoromethyl)phenyl]acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=C(C=C(C=C1)C)C(F)(F)F)(F)F)=O)=O)=O GVBWAGDULNKFNC-UHFFFAOYSA-N 0.000 claims 3
• CPFHBSQWAXYFQL-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-[5-(trifluoromethylsulfanyl)pyridin-2-yl]acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=NC=C(C=C1)SC(F)(F)F)(F)F)=O)=O)=O CPFHBSQWAXYFQL-UHFFFAOYSA-N 0.000 claims 3
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