CA3038820A1 - Substituted 1h-imidazo[4,5-b]pyridin-2(3h)-ones and their use as glun2b receptor modulators - Google Patents

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Publication number

CA3038820A1

CA3038820A1 CA3038820A CA3038820A CA3038820A1 CA 3038820 A1 CA3038820 A1 CA 3038820A1 CA 3038820 A CA3038820 A CA 3038820A CA 3038820 A CA3038820 A CA 3038820A CA 3038820 A1 CA3038820 A1 CA 3038820A1

Authority

CA

Canada

Prior art keywords

methyl

imidazo

pyridin

phenyl

oxo

Prior art date

2016-10-06

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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• PGDIPOWQYRAOSK-UHFFFAOYSA-N 1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical class C1=CN=C2NC(=O)NC2=C1 PGDIPOWQYRAOSK-UHFFFAOYSA-N 0.000 title 1
• 108010054200 NR2B NMDA receptor Proteins 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 527
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 70
• 238000000034 method Methods 0.000 claims abstract description 47
• 201000010099 disease Diseases 0.000 claims abstract description 31
• 108010038912 Retinoid X Receptors Proteins 0.000 claims abstract description 24
• 238000011282 treatment Methods 0.000 claims abstract description 24
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
• 230000000694 effects Effects 0.000 claims abstract description 15
• 230000001404 mediated effect Effects 0.000 claims abstract description 15
• 102000034527 Retinoid X Receptors Human genes 0.000 claims abstract 5
• -1 2,6-diazaspiro[3.3]heptan-6-yl Chemical group 0.000 claims description 443
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 195
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 144
• 150000003839 salts Chemical class 0.000 claims description 70
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 57
• JXXWJMUPNZDILL-UHFFFAOYSA-N imidazo[4,5-b]pyridin-2-one Chemical compound C1=CC=NC2=NC(=O)N=C21 JXXWJMUPNZDILL-UHFFFAOYSA-N 0.000 claims description 54
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 53
• 125000004076 pyridyl group Chemical group 0.000 claims description 52
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 48
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 45
• 125000005843 halogen group Chemical group 0.000 claims description 44
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 42
• 125000001544 thienyl group Chemical group 0.000 claims description 41
• 208000035475 disorder Diseases 0.000 claims description 38
• 239000012453 solvate Substances 0.000 claims description 35
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 34
• 125000003566 oxetanyl group Chemical group 0.000 claims description 33
• 150000001204 N-oxides Chemical class 0.000 claims description 32
• 208000002193 Pain Diseases 0.000 claims description 27
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 24
• 125000000335 thiazolyl group Chemical group 0.000 claims description 24
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 23
• 125000002393 azetidinyl group Chemical group 0.000 claims description 23
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 21
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 20
• 229910052731 fluorine Inorganic materials 0.000 claims description 19
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 17
• 230000000155 isotopic effect Effects 0.000 claims description 16
• 125000002757 morpholinyl group Chemical group 0.000 claims description 16
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 15
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 15
• VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical group F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 14
• 229910052801 chlorine Inorganic materials 0.000 claims description 13
• 206010015037 epilepsy Diseases 0.000 claims description 13
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 12
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 12
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 9
• 208000020925 Bipolar disease Diseases 0.000 claims description 9
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 9
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 9
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 9
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 9
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 8
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 8
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 8
• 125000000623 heterocyclic group Chemical group 0.000 claims description 8
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 8
• 230000036407 pain Effects 0.000 claims description 8
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
• 125000001425 triazolyl group Chemical group 0.000 claims description 8
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 7
• 208000028552 Treatment-Resistant Depressive disease Diseases 0.000 claims description 7
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 7
• 208000024714 major depressive disease Diseases 0.000 claims description 7
• 230000004770 neurodegeneration Effects 0.000 claims description 7
• 125000003386 piperidinyl group Chemical group 0.000 claims description 7
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 7
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 6
• 208000020706 Autistic disease Diseases 0.000 claims description 6
• 206010011416 Croup infectious Diseases 0.000 claims description 6
• 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 6
• 208000012661 Dyskinesia Diseases 0.000 claims description 6
• 208000006011 Stroke Diseases 0.000 claims description 6
• 206010008118 cerebral infarction Diseases 0.000 claims description 6
• 201000010549 croup Diseases 0.000 claims description 6
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 6
• 125000004193 piperazinyl group Chemical group 0.000 claims description 6
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 5
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 5
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 claims description 4
• 208000024827 Alzheimer disease Diseases 0.000 claims description 4
• 206010003805 Autism Diseases 0.000 claims description 4
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 4
• 208000018737 Parkinson disease Diseases 0.000 claims description 4
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 4
• 208000029560 autism spectrum disease Diseases 0.000 claims description 4
• 201000006417 multiple sclerosis Diseases 0.000 claims description 4
• 201000000980 schizophrenia Diseases 0.000 claims description 4
• BIUDHHGROGJSHN-UHFFFAOYSA-N 4-fluoro-3-(trifluoromethyl)benzaldehyde Chemical group FC1=CC=C(C=O)C=C1C(F)(F)F BIUDHHGROGJSHN-UHFFFAOYSA-N 0.000 claims description 3
• 208000023105 Huntington disease Diseases 0.000 claims description 3
• 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
• VWIMYYMCCXCKLC-UHFFFAOYSA-N 2-[3-methyl-2-oxo-6-[3-(trifluoromethyl)phenyl]imidazo[4,5-b]pyridin-1-yl]acetic acid Chemical compound CN1C(N(C=2C1=NC=C(C=2)C1=CC(=CC=C1)C(F)(F)F)CC(=O)O)=O VWIMYYMCCXCKLC-UHFFFAOYSA-N 0.000 claims description 2
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
• ZLPSBEDNVFVVTO-UHFFFAOYSA-N 3-methyl-1-(oxetan-2-ylmethyl)-6-[3-(trifluoromethyl)phenyl]imidazo[4,5-b]pyridin-2-one Chemical compound CN1C(=O)N(CC2CCO2)C2=C1N=CC(=C2)C1=CC=CC(=C1)C(F)(F)F ZLPSBEDNVFVVTO-UHFFFAOYSA-N 0.000 claims description 2
• AAZKWSOTSFMXAU-UHFFFAOYSA-N 6-(4-fluoro-3-methylphenyl)-1-[(5-methylpyridin-3-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC=1C=NC=C(C=1)C)=O)C AAZKWSOTSFMXAU-UHFFFAOYSA-N 0.000 claims description 2
• GYFCCYHGQFJSFO-UHFFFAOYSA-N 6-[2-fluoro-3-(trifluoromethyl)phenyl]-3-methyl-1-(oxetan-2-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound CN1C(=O)N(CC2CCO2)C2=C1N=CC(=C2)C1=CC=CC(=C1F)C(F)(F)F GYFCCYHGQFJSFO-UHFFFAOYSA-N 0.000 claims description 2
• QPDGFUCDSZWJGK-UHFFFAOYSA-N 6-[5-(difluoromethyl)-2-fluorophenyl]-3-methyl-1-(pyridazin-3-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound FC(C=1C=CC(=C(C=1)C=1C=C2C(=NC=1)N(C(N2CC=1N=NC=CC=1)=O)C)F)F QPDGFUCDSZWJGK-UHFFFAOYSA-N 0.000 claims description 2
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 2
• 208000035143 Bacterial infection Diseases 0.000 claims description 2
• 201000006474 Brain Ischemia Diseases 0.000 claims description 2
• 206010008120 Cerebral ischaemia Diseases 0.000 claims description 2
• 208000028698 Cognitive impairment Diseases 0.000 claims description 2
• 206010019196 Head injury Diseases 0.000 claims description 2
• 208000020358 Learning disease Diseases 0.000 claims description 2
• 208000026139 Memory disease Diseases 0.000 claims description 2
• 208000019695 Migraine disease Diseases 0.000 claims description 2
• 208000037581 Persistent Infection Diseases 0.000 claims description 2
• 201000009916 Postpartum depression Diseases 0.000 claims description 2
• 230000001580 bacterial effect Effects 0.000 claims description 2
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 2
• 208000010877 cognitive disease Diseases 0.000 claims description 2
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
• 206010014599 encephalitis Diseases 0.000 claims description 2
• 201000003723 learning disability Diseases 0.000 claims description 2
• 206010027599 migraine Diseases 0.000 claims description 2
• 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims description 2
• 208000012672 seasonal affective disease Diseases 0.000 claims description 2
• 208000020431 spinal cord injury Diseases 0.000 claims description 2
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 4
• VBYDZMQKWHOANY-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-3-methyl-6-[5-(trifluoromethyl)thiophen-2-yl]imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(N(C2=NC=C(C=C21)C=1SC(=CC=1)C(F)(F)F)C)=O)=O VBYDZMQKWHOANY-UHFFFAOYSA-N 0.000 claims 2
• CGNGKLZWRKWFHY-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-6-(2,4-difluoro-3-methylphenyl)-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(N(C2=NC=C(C=C21)C1=C(C(=C(C=C1)F)C)F)C)=O)=O CGNGKLZWRKWFHY-UHFFFAOYSA-N 0.000 claims 2
• VUSYMWQENCACHC-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-6-(4-fluoro-3-methylphenyl)-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(N(C2=NC=C(C=C21)C1=CC(=C(C=C1)F)C)C)=O)=O VUSYMWQENCACHC-UHFFFAOYSA-N 0.000 claims 2
• INTCEBHIEDIHMH-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-6-[5-(trifluoromethyl)thiophen-2-yl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(NC2=NC=C(C=C21)C=1SC(=CC=1)C(F)(F)F)=O)=O INTCEBHIEDIHMH-UHFFFAOYSA-N 0.000 claims 2
• IJRVELKVEKRDRM-UHFFFAOYSA-N 2-[6-(4-fluoro-3-methylphenyl)-3-methyl-2-oxoimidazo[4,5-b]pyridin-1-yl]-N,N-dimethylacetamide Chemical compound FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)N(C(N2CC(=O)N(C)C)=O)C)C IJRVELKVEKRDRM-UHFFFAOYSA-N 0.000 claims 2
• LZDMVQGCGHJVOI-UHFFFAOYSA-N N,N-dimethyl-2-[3-methyl-2-oxo-6-[5-(trifluoromethyl)thiophen-2-yl]imidazo[4,5-b]pyridin-1-yl]acetamide Chemical compound CN(C(CN1C(N(C2=NC=C(C=C21)C=1SC(=CC=1)C(F)(F)F)C)=O)=O)C LZDMVQGCGHJVOI-UHFFFAOYSA-N 0.000 claims 2
• BDOKYOYGAUFDTD-UHFFFAOYSA-N 1-(2-cyclobutyl-2-oxoethyl)-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound C1(CCC1)C(CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O)=O BDOKYOYGAUFDTD-UHFFFAOYSA-N 0.000 claims 1
• JJKRQIAUPSBKIY-UHFFFAOYSA-N 1-(2-cyclopropyl-2-hydroxyethyl)-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound OC(Cn1c2cc(cnc2[nH]c1=O)-c1cccc(c1)C(F)(F)F)C1CC1 JJKRQIAUPSBKIY-UHFFFAOYSA-N 0.000 claims 1
• BYXIZAICNRKJLY-UHFFFAOYSA-N 1-(2-cyclopropyl-2-oxoethyl)-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound C1(CC1)C(CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O)=O BYXIZAICNRKJLY-UHFFFAOYSA-N 0.000 claims 1
• PBZWKRSMFNXMDK-UHFFFAOYSA-N 1-(2-hydroxy-3-methylbutyl)-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CC(C)C(O)Cn1c2cc(cnc2[nH]c1=O)-c1cccc(c1)C(F)(F)F PBZWKRSMFNXMDK-UHFFFAOYSA-N 0.000 claims 1
• LFIZMGPBXZHFCS-UHFFFAOYSA-N 1-(2-hydroxybutyl)-6-(3-methylphenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CCC(O)Cn1c2cc(cnc2[nH]c1=O)-c1cccc(C)c1 LFIZMGPBXZHFCS-UHFFFAOYSA-N 0.000 claims 1
• KUJLLTMWEAEWOL-UHFFFAOYSA-N 1-(2-hydroxybutyl)-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CCC(O)Cn1c2cc(cnc2[nH]c1=O)-c1cccc(c1)C(F)(F)F KUJLLTMWEAEWOL-UHFFFAOYSA-N 0.000 claims 1
• NHNDDIFFCIVWQO-UHFFFAOYSA-N 1-(2-morpholin-4-yl-2-oxoethyl)-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound O1CCN(CC1)C(CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O)=O NHNDDIFFCIVWQO-UHFFFAOYSA-N 0.000 claims 1
• FIXAUOICSGCIGR-UHFFFAOYSA-N 1-(2-oxo-2-piperidin-1-ylethyl)-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound O=C(CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O)N1CCCCC1 FIXAUOICSGCIGR-UHFFFAOYSA-N 0.000 claims 1
• QJYHMGQXPDXLRE-UHFFFAOYSA-N 1-(2-oxo-2-pyrrolidin-1-ylethyl)-6-(1,3-thiazol-5-yl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound O=C(CN1C(NC2=NC=C(C=C21)C1=CN=CS1)=O)N1CCCC1 QJYHMGQXPDXLRE-UHFFFAOYSA-N 0.000 claims 1
• OEQSIDVSRQIXCR-UHFFFAOYSA-N 1-(2-oxo-2-pyrrolidin-1-ylethyl)-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound O=C(CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O)N1CCCC1 OEQSIDVSRQIXCR-UHFFFAOYSA-N 0.000 claims 1
• XTLUOTXBFBHKJH-UHFFFAOYSA-N 1-(2-oxo-2-thiophen-2-ylethyl)-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound O=C(CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O)C=1SC=CC=1 XTLUOTXBFBHKJH-UHFFFAOYSA-N 0.000 claims 1
• RKFDMAFHXUKWFT-UHFFFAOYSA-N 1-(2-oxobutyl)-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound O=C(CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O)CC RKFDMAFHXUKWFT-UHFFFAOYSA-N 0.000 claims 1
• GRRSHWZJSOQJSQ-UHFFFAOYSA-N 1-(2-piperidin-1-ylethyl)-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCCCC1)CCN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O GRRSHWZJSOQJSQ-UHFFFAOYSA-N 0.000 claims 1
• OZELIZZCCMSXOT-UHFFFAOYSA-N 1-(2-pyrrolidin-1-ylethyl)-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCCC1)CCN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O OZELIZZCCMSXOT-UHFFFAOYSA-N 0.000 claims 1
• QTRIXDQRYLDLJZ-UHFFFAOYSA-N 1-(2H-tetrazol-5-ylmethyl)-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N=1NN=NC=1CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O QTRIXDQRYLDLJZ-UHFFFAOYSA-N 0.000 claims 1
• YXILZDWUUOIACP-UHFFFAOYSA-N 1-(3,3-dimethyl-2-oxobutyl)-6-(3-fluoro-4-methoxyphenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CC(C(CN1C(NC2=NC=C(C=C21)C1=CC(=C(C=C1)OC)F)=O)=O)(C)C YXILZDWUUOIACP-UHFFFAOYSA-N 0.000 claims 1
• LYTXKAPDKRSJRU-UHFFFAOYSA-N 1-(3,3-dimethyl-2-oxobutyl)-6-(4-methoxy-3-methylphenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CC(C(CN1C(NC2=NC=C(C=C21)C1=CC(=C(C=C1)OC)C)=O)=O)(C)C LYTXKAPDKRSJRU-UHFFFAOYSA-N 0.000 claims 1
• GHHBZKVDJJILCY-UHFFFAOYSA-N 1-(3,3-dimethyl-2-oxobutyl)-6-(4-methoxyphenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CC(C(CN1C(NC2=NC=C(C=C21)C1=CC=C(C=C1)OC)=O)=O)(C)C GHHBZKVDJJILCY-UHFFFAOYSA-N 0.000 claims 1
• AHTZCTAOVDEOCW-UHFFFAOYSA-N 1-(3,3-dimethyl-2-oxobutyl)-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CC(C(CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O)=O)(C)C AHTZCTAOVDEOCW-UHFFFAOYSA-N 0.000 claims 1
• LMMUZBVTXQRKHV-UHFFFAOYSA-N 1-(3-methyl-2-oxobutyl)-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CC(C(CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O)=O)C LMMUZBVTXQRKHV-UHFFFAOYSA-N 0.000 claims 1
• ACVJVSGXUFHJFO-UHFFFAOYSA-N 1-(azetidin-2-ylmethyl)-3-methyl-6-[3-(trifluoromethyl)phenyl]imidazo[4,5-b]pyridin-2-one Chemical compound Cn1c2ncc(cc2n(CC2CCN2)c1=O)-c1cccc(c1)C(F)(F)F ACVJVSGXUFHJFO-UHFFFAOYSA-N 0.000 claims 1
• IRFYUKRBLYNANC-UHFFFAOYSA-N 1-(azetidin-2-ylmethyl)-6-(2,3-dichlorophenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound Clc1cccc(c1Cl)-c1cnc2[nH]c(=O)n(CC3CCN3)c2c1 IRFYUKRBLYNANC-UHFFFAOYSA-N 0.000 claims 1
• KZGINNLKVIAAIV-UHFFFAOYSA-N 1-(azetidin-2-ylmethyl)-6-(4-fluorophenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound Fc1ccc(cc1)-c1cnc2[nH]c(=O)n(CC3CCN3)c2c1 KZGINNLKVIAAIV-UHFFFAOYSA-N 0.000 claims 1
• VKQKBJFYHCDWAK-UHFFFAOYSA-N 1-(azetidin-2-ylmethyl)-6-[2-fluoro-3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound Fc1c(cccc1C(F)(F)F)-c1cnc2[nH]c(=O)n(CC3CCN3)c2c1 VKQKBJFYHCDWAK-UHFFFAOYSA-N 0.000 claims 1
• KNGAMNSCOSZWBJ-UHFFFAOYSA-N 1-(azetidin-2-ylmethyl)-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC(F)(F)c1cccc(c1)-c1cnc2[nH]c(=O)n(CC3CCN3)c2c1 KNGAMNSCOSZWBJ-UHFFFAOYSA-N 0.000 claims 1
• LXJPOIZRXRSNJQ-UHFFFAOYSA-N 1-(azetidin-2-ylmethyl)-6-[4-fluoro-3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound Fc1ccc(cc1C(F)(F)F)-c1cnc2[nH]c(=O)n(CC3CCN3)c2c1 LXJPOIZRXRSNJQ-UHFFFAOYSA-N 0.000 claims 1
• GSLVVTAGIMVVMQ-UHFFFAOYSA-N 1-(azetidin-2-ylmethyl)-6-phenyl-3H-imidazo[4,5-b]pyridin-2-one Chemical compound O=c1[nH]c2ncc(cc2n1CC1CCN1)-c1ccccc1 GSLVVTAGIMVVMQ-UHFFFAOYSA-N 0.000 claims 1
• UCBJIHXWODXYEU-UHFFFAOYSA-N 1-(cyclopropylmethyl)-6-(2,4-dimethoxyphenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound C1(CC1)CN1C(NC2=NC=C(C=C21)C1=C(C=C(C=C1)OC)OC)=O UCBJIHXWODXYEU-UHFFFAOYSA-N 0.000 claims 1
• SETFLIUZCWCVCA-UHFFFAOYSA-N 1-(cyclopropylmethyl)-6-(2-ethoxy-5-fluorophenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound C1(CC1)CN1C(NC2=NC=C(C=C21)C1=C(C=CC(=C1)F)OCC)=O SETFLIUZCWCVCA-UHFFFAOYSA-N 0.000 claims 1
• JGYJDUSAFDKVFP-UHFFFAOYSA-N 1-(cyclopropylmethyl)-6-(3,5-difluorophenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound C1(CC1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC(=C1)F)F)=O JGYJDUSAFDKVFP-UHFFFAOYSA-N 0.000 claims 1
• CVYRLCXFKMIEMZ-UHFFFAOYSA-N 1-(cyclopropylmethyl)-6-(3,5-dimethylphenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound C1(CC1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC(=C1)C)C)=O CVYRLCXFKMIEMZ-UHFFFAOYSA-N 0.000 claims 1
• NSAVCHKGSHEUBW-UHFFFAOYSA-N 1-(cyclopropylmethyl)-6-(3-fluoro-4-methoxyphenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound C1(CC1)CN1C(NC2=NC=C(C=C21)C1=CC(=C(C=C1)OC)F)=O NSAVCHKGSHEUBW-UHFFFAOYSA-N 0.000 claims 1
• RMBTZWSWSBMRJZ-UHFFFAOYSA-N 1-(cyclopropylmethyl)-6-(4-fluoro-2-methoxyphenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound C1(CC1)CN1C(NC2=NC=C(C=C21)C1=C(C=C(C=C1)F)OC)=O RMBTZWSWSBMRJZ-UHFFFAOYSA-N 0.000 claims 1
• DXYVEQFPYUTGNP-UHFFFAOYSA-N 1-(cyclopropylmethyl)-6-(4-methoxy-3-methylphenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound C1(CC1)CN1C(NC2=NC=C(C=C21)C1=CC(=C(C=C1)OC)C)=O DXYVEQFPYUTGNP-UHFFFAOYSA-N 0.000 claims 1
• FIHIIXJKTJIOKH-UHFFFAOYSA-N 1-(cyclopropylmethyl)-6-(4-methoxyphenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound C1(CC1)CN1C(NC2=NC=C(C=C21)C1=CC=C(C=C1)OC)=O FIHIIXJKTJIOKH-UHFFFAOYSA-N 0.000 claims 1
• GLXFHPWOPLUMRJ-UHFFFAOYSA-N 1-(cyclopropylmethyl)-6-[3-(dimethylamino)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound C1(CC1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)N(C)C)=O GLXFHPWOPLUMRJ-UHFFFAOYSA-N 0.000 claims 1
• XFUIFYSHULPOQD-UHFFFAOYSA-N 1-(cyclopropylmethyl)-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound C1(CC1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O XFUIFYSHULPOQD-UHFFFAOYSA-N 0.000 claims 1
• IBXUFNNVUMHHRO-UHFFFAOYSA-N 1-(cyclopropylmethyl)-6-thiophen-2-yl-3H-imidazo[4,5-b]pyridin-2-one Chemical compound C1(CC1)CN1C(NC2=NC=C(C=C21)C=1SC=CC=1)=O IBXUFNNVUMHHRO-UHFFFAOYSA-N 0.000 claims 1
• YNXOHUUZKDPAQP-UHFFFAOYSA-N 1-(morpholin-2-ylmethyl)-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC(F)(F)c1cccc(c1)-c1cnc2[nH]c(=O)n(CC3CNCCO3)c2c1 YNXOHUUZKDPAQP-UHFFFAOYSA-N 0.000 claims 1
• GHTOKSXVZIAVJZ-UHFFFAOYSA-N 1-(oxan-2-ylmethyl)-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC(F)(F)c1cccc(c1)-c1cnc2[nH]c(=O)n(CC3CCCCO3)c2c1 GHTOKSXVZIAVJZ-UHFFFAOYSA-N 0.000 claims 1
• LYAQGBFZDHGDNN-UHFFFAOYSA-N 1-(oxetan-2-ylmethyl)-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC(F)(F)c1cccc(c1)-c1cnc2[nH]c(=O)n(CC3CCO3)c2c1 LYAQGBFZDHGDNN-UHFFFAOYSA-N 0.000 claims 1
• PZAMDDZOGCICLL-UHFFFAOYSA-N 1-(pyrazin-2-ylmethyl)-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1=C(C=NC=C1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O PZAMDDZOGCICLL-UHFFFAOYSA-N 0.000 claims 1
• ACHUMLNAQOOCJO-UHFFFAOYSA-N 1-(pyridazin-3-ylmethyl)-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1=NC(=CC=C1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O ACHUMLNAQOOCJO-UHFFFAOYSA-N 0.000 claims 1
• NUOJESOUQWSUMZ-UHFFFAOYSA-N 1-(pyridin-3-ylmethyl)-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1=CC(=CC=C1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O NUOJESOUQWSUMZ-UHFFFAOYSA-N 0.000 claims 1
• DVGNEKAVVRCWKU-UHFFFAOYSA-N 1-(pyridin-4-ylmethyl)-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1=CC=C(C=C1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O DVGNEKAVVRCWKU-UHFFFAOYSA-N 0.000 claims 1
• BBGPTHOMBMTFQT-UHFFFAOYSA-N 1-(pyrimidin-2-ylmethyl)-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1=C(N=CC=C1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O BBGPTHOMBMTFQT-UHFFFAOYSA-N 0.000 claims 1
• QXMSYSKPRIHEAP-UHFFFAOYSA-N 1-(pyrimidin-4-ylmethyl)-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1=CN=C(C=C1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O QXMSYSKPRIHEAP-UHFFFAOYSA-N 0.000 claims 1
• CPPDODNXZMDTEG-UHFFFAOYSA-N 1-(pyrimidin-5-ylmethyl)-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1=CN=CC(=C1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O CPPDODNXZMDTEG-UHFFFAOYSA-N 0.000 claims 1
• IHKZSTGFGKSRDS-UHFFFAOYSA-N 1-(thiadiazol-4-ylmethyl)-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound S1N=NC(=C1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O IHKZSTGFGKSRDS-UHFFFAOYSA-N 0.000 claims 1
• YCAUWABCWIMHRX-UHFFFAOYSA-N 1-[(1,5-dimethylpyrazol-3-yl)methyl]-6-(4-fluorophenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CN1N=C(C=C1C)CN1C(NC2=NC=C(C=C21)C1=CC=C(C=C1)F)=O YCAUWABCWIMHRX-UHFFFAOYSA-N 0.000 claims 1
• UMRZYPMPZRMSET-UHFFFAOYSA-N 1-[(2,2-difluorocyclopropyl)methyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC(F)(F)c1cccc(c1)-c1cnc2[nH]c(=O)n(CC3CC3(F)F)c2c1 UMRZYPMPZRMSET-UHFFFAOYSA-N 0.000 claims 1
• HIZBSKHOIKDMNU-UHFFFAOYSA-N 1-[(2-methoxypyridin-3-yl)methyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound COC1=NC=CC=C1CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O HIZBSKHOIKDMNU-UHFFFAOYSA-N 0.000 claims 1
• QUIRFFFDXSJZMN-UHFFFAOYSA-N 1-[(2-methylpyrimidin-4-yl)methyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CC1=NC=CC(=N1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O QUIRFFFDXSJZMN-UHFFFAOYSA-N 0.000 claims 1
• SVIMUIDZIBPDKW-UHFFFAOYSA-N 1-[(2-methylpyrimidin-5-yl)methyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CC1=NC=C(C=N1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O SVIMUIDZIBPDKW-UHFFFAOYSA-N 0.000 claims 1
• QKGAHHXJNYDKBJ-UHFFFAOYSA-N 1-[(2-oxo-1H-pyridin-3-yl)methyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound O=C1NC=CC=C1CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O QKGAHHXJNYDKBJ-UHFFFAOYSA-N 0.000 claims 1
• KBOARIPJVLGIGZ-CYBMUJFWSA-N 1-[(2R)-2-hydroxybutyl]-6-(4-methoxyphenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CC[C@@H](O)Cn1c2cc(cnc2[nH]c1=O)-c1ccc(OC)cc1 KBOARIPJVLGIGZ-CYBMUJFWSA-N 0.000 claims 1
• KZJADJOMNNLBQP-UHFFFAOYSA-N 1-[(3,5-dimethoxyphenyl)methyl]-6-(2-fluoro-6-methoxyphenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound COC=1C=C(C=C(C=1)OC)CN1C(NC2=NC=C(C=C21)C1=C(C=CC=C1OC)F)=O KZJADJOMNNLBQP-UHFFFAOYSA-N 0.000 claims 1
• RRERTRUHVYIKMV-UHFFFAOYSA-N 1-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]-6-(2-ethoxy-5-fluorophenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CC1=NOC(=C1CN1C(NC2=NC=C(C=C21)C1=C(C=CC(=C1)F)OCC)=O)C RRERTRUHVYIKMV-UHFFFAOYSA-N 0.000 claims 1
• BUALAFNRAKGTQE-UHFFFAOYSA-N 1-[(3-chlorophenyl)methyl]-6-(3,5-difluorophenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound ClC=1C=C(C=CC=1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC(=C1)F)F)=O BUALAFNRAKGTQE-UHFFFAOYSA-N 0.000 claims 1
• VCFCLGGJCVZEMB-UHFFFAOYSA-N 1-[(3-chlorophenyl)methyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound ClC=1C=C(C=CC=1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O VCFCLGGJCVZEMB-UHFFFAOYSA-N 0.000 claims 1
• PTQCJPQEAHNTHS-UHFFFAOYSA-N 1-[(3-fluoro-4-methoxyphenyl)methyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC=1C=C(C=CC=1OC)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O PTQCJPQEAHNTHS-UHFFFAOYSA-N 0.000 claims 1
• MOEIKZSWXWTBDK-UHFFFAOYSA-N 1-[(3-fluoro-5-methylpyridin-2-yl)methyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC=1C(=NC=C(C=1)C)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O MOEIKZSWXWTBDK-UHFFFAOYSA-N 0.000 claims 1
• JKRAGWHFLNRQHO-UHFFFAOYSA-N 1-[(3-fluorooxetan-3-yl)methyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1(COC1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O JKRAGWHFLNRQHO-UHFFFAOYSA-N 0.000 claims 1
• SBSFOSMFVRHSJM-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]-6-(4-methoxy-3-methylphenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC=1C=C(C=CC=1)CN1C(NC2=NC=C(C=C21)C1=CC(=C(C=C1)OC)C)=O SBSFOSMFVRHSJM-UHFFFAOYSA-N 0.000 claims 1
• SVJNLZXTSQVMLH-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC=1C=C(C=CC=1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O SVJNLZXTSQVMLH-UHFFFAOYSA-N 0.000 claims 1
• XFFRZFPCVJAFLE-UHFFFAOYSA-N 1-[(3-methoxyphenyl)methyl]-6-(4-methylthiophen-2-yl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound COC=1C=C(C=CC=1)CN1C(NC2=NC=C(C=C21)C=1SC=C(C=1)C)=O XFFRZFPCVJAFLE-UHFFFAOYSA-N 0.000 claims 1
• CPPRSSSJOIOEHN-UHFFFAOYSA-N 1-[(3-methoxyphenyl)methyl]-6-pyridin-3-yl-3H-imidazo[4,5-b]pyridin-2-one Chemical compound COC=1C=C(C=CC=1)CN1C(NC2=NC=C(C=C21)C=1C=NC=CC=1)=O CPPRSSSJOIOEHN-UHFFFAOYSA-N 0.000 claims 1
• XGAALRYJEMCKKS-UHFFFAOYSA-N 1-[(3-methoxypyridin-2-yl)methyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound COC=1C(=NC=CC=1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O XGAALRYJEMCKKS-UHFFFAOYSA-N 0.000 claims 1
• VHKZQISBJDBKPW-UHFFFAOYSA-N 1-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-6-(4-methylthiophen-2-yl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CC1=NOC(=N1)CN1C(NC2=NC=C(C=C21)C=1SC=C(C=1)C)=O VHKZQISBJDBKPW-UHFFFAOYSA-N 0.000 claims 1
• ITJIBZJLHQUXLR-UHFFFAOYSA-N 1-[(3-methylpyridin-2-yl)methyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CC=1C(=NC=CC=1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O ITJIBZJLHQUXLR-UHFFFAOYSA-N 0.000 claims 1
• BUUIFURXARJXQG-UHFFFAOYSA-N 1-[(4-fluoro-3-methylphenyl)methyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=C(C=C1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O)C BUUIFURXARJXQG-UHFFFAOYSA-N 0.000 claims 1
• YMBVXISLWUJQMX-UHFFFAOYSA-N 1-[(4-methylpyridin-3-yl)methyl]-6-(3,4,5-trifluorophenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CC1=C(C=NC=C1)CN1C(NC2=NC=C(C=C21)C1=CC(=C(C(=C1)F)F)F)=O YMBVXISLWUJQMX-UHFFFAOYSA-N 0.000 claims 1
• ONQNYOWDDFFFNW-UHFFFAOYSA-N 1-[(4-methylpyridin-3-yl)methyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CC1=C(C=NC=C1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O ONQNYOWDDFFFNW-UHFFFAOYSA-N 0.000 claims 1
• DREXYQHKKCFKSM-UHFFFAOYSA-N 1-[(5-chloropyridin-3-yl)methyl]-3-methyl-6-(3,4,5-trifluorophenyl)imidazo[4,5-b]pyridin-2-one Chemical compound ClC=1C=C(C=NC=1)CN1C(N(C2=NC=C(C=C21)C1=CC(=C(C(=C1)F)F)F)C)=O DREXYQHKKCFKSM-UHFFFAOYSA-N 0.000 claims 1
• SRMOTNBGNDRWCU-UHFFFAOYSA-N 1-[(5-chloropyridin-3-yl)methyl]-3-methyl-6-(3-methylphenyl)imidazo[4,5-b]pyridin-2-one Chemical compound ClC=1C=C(C=NC=1)CN1C(N(C2=NC=C(C=C21)C=1C=C(C=CC=1)C)C)=O SRMOTNBGNDRWCU-UHFFFAOYSA-N 0.000 claims 1
• HAZWBAYUBWKFMS-UHFFFAOYSA-N 1-[(5-chloropyridin-3-yl)methyl]-3-methyl-6-[3-(trifluoromethyl)phenyl]imidazo[4,5-b]pyridin-2-one Chemical compound ClC=1C=C(C=NC=1)CN1C(N(C2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)C)=O HAZWBAYUBWKFMS-UHFFFAOYSA-N 0.000 claims 1
• RCEDLCXWCZORSL-UHFFFAOYSA-N 1-[(5-chloropyridin-3-yl)methyl]-3-methyl-6-[5-(trifluoromethyl)thiophen-2-yl]imidazo[4,5-b]pyridin-2-one Chemical compound ClC=1C=C(C=NC=1)CN1C(N(C2=NC=C(C=C21)C=1SC(=CC=1)C(F)(F)F)C)=O RCEDLCXWCZORSL-UHFFFAOYSA-N 0.000 claims 1
• IFFCQSBYKDRCPL-UHFFFAOYSA-N 1-[(5-chloropyridin-3-yl)methyl]-6-(2,3-difluorophenyl)-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound ClC=1C=C(C=NC=1)CN1C(N(C2=NC=C(C=C21)C1=C(C(=CC=C1)F)F)C)=O IFFCQSBYKDRCPL-UHFFFAOYSA-N 0.000 claims 1
• VCYIJUBHOPBLMC-UHFFFAOYSA-N 1-[(5-chloropyridin-3-yl)methyl]-6-(2,4-difluoro-3-methylphenyl)-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound ClC=1C=C(C=NC=1)CN1C(N(C2=NC=C(C=C21)C1=C(C(=C(C=C1)F)C)F)C)=O VCYIJUBHOPBLMC-UHFFFAOYSA-N 0.000 claims 1
• NKWLKQFLBMKNDT-UHFFFAOYSA-N 1-[(5-chloropyridin-3-yl)methyl]-6-(2-fluoro-3-methylphenyl)-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound ClC=1C=C(C=NC=1)CN1C(N(C2=NC=C(C=C21)C1=C(C(=CC=C1)C)F)C)=O NKWLKQFLBMKNDT-UHFFFAOYSA-N 0.000 claims 1
• UBFKFSQDQMHEMX-UHFFFAOYSA-N 1-[(5-chloropyridin-3-yl)methyl]-6-(3,4-difluorophenyl)-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound ClC=1C=C(C=NC=1)CN1C(N(C2=NC=C(C=C21)C1=CC(=C(C=C1)F)F)C)=O UBFKFSQDQMHEMX-UHFFFAOYSA-N 0.000 claims 1
• CLVQRUAXXOXWJA-UHFFFAOYSA-N 1-[(5-chloropyridin-3-yl)methyl]-6-(4-fluoro-3-methylphenyl)-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound ClC=1C=C(C=NC=1)CN1C(N(C2=NC=C(C=C21)C1=CC(=C(C=C1)F)C)C)=O CLVQRUAXXOXWJA-UHFFFAOYSA-N 0.000 claims 1
• ABYQSLLDZNRMNE-UHFFFAOYSA-N 1-[(5-fluoropyridin-3-yl)methyl]-3-methyl-6-(2,3,4-trifluorophenyl)imidazo[4,5-b]pyridin-2-one Chemical compound FC=1C=C(C=NC=1)CN1C(N(C2=NC=C(C=C21)C1=C(C(=C(C=C1)F)F)F)C)=O ABYQSLLDZNRMNE-UHFFFAOYSA-N 0.000 claims 1
• YIJDSUXVDSOZGA-UHFFFAOYSA-N 1-[(5-fluoropyridin-3-yl)methyl]-3-methyl-6-(3,4,5-trifluorophenyl)imidazo[4,5-b]pyridin-2-one Chemical compound FC=1C=C(C=NC=1)CN1C(N(C2=NC=C(C=C21)C1=CC(=C(C(=C1)F)F)F)C)=O YIJDSUXVDSOZGA-UHFFFAOYSA-N 0.000 claims 1
• DVMMXGXEXBVNQN-UHFFFAOYSA-N 1-[(5-fluoropyridin-3-yl)methyl]-3-methyl-6-(3-methylphenyl)imidazo[4,5-b]pyridin-2-one Chemical compound FC=1C=C(C=NC=1)CN1C(N(C2=NC=C(C=C21)C=1C=C(C=CC=1)C)C)=O DVMMXGXEXBVNQN-UHFFFAOYSA-N 0.000 claims 1
• BVJRWICJPYKCNA-UHFFFAOYSA-N 1-[(5-fluoropyridin-3-yl)methyl]-3-methyl-6-[3-(trifluoromethoxy)phenyl]imidazo[4,5-b]pyridin-2-one Chemical compound FC=1C=C(C=NC=1)CN1C(N(C2=NC=C(C=C21)C1=CC(=CC=C1)OC(F)(F)F)C)=O BVJRWICJPYKCNA-UHFFFAOYSA-N 0.000 claims 1
• GFKHITIDTPMUNZ-UHFFFAOYSA-N 1-[(5-fluoropyridin-3-yl)methyl]-6-[3-(trifluoromethoxy)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC=1C=C(C=NC=1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)OC(F)(F)F)=O GFKHITIDTPMUNZ-UHFFFAOYSA-N 0.000 claims 1
• SINMJAASHBAUPT-UHFFFAOYSA-N 1-[(5-fluoropyridin-3-yl)methyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC=1C=C(C=NC=1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O SINMJAASHBAUPT-UHFFFAOYSA-N 0.000 claims 1
• BKMIXCRIZYIKGB-UHFFFAOYSA-N 1-[(5-fluoropyrimidin-2-yl)methyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC=1C=NC(=NC=1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O BKMIXCRIZYIKGB-UHFFFAOYSA-N 0.000 claims 1
• XVKBTXGTFZBYCB-UHFFFAOYSA-N 1-[(5-methyl-1,2-oxazol-3-yl)methyl]-6-(2-methylphenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CC1=CC(=NO1)CN1C(NC2=NC=C(C=C21)C1=C(C=CC=C1)C)=O XVKBTXGTFZBYCB-UHFFFAOYSA-N 0.000 claims 1
• BKNYUJKUJILMNO-UHFFFAOYSA-N 1-[(5-methyl-1,2-oxazol-3-yl)methyl]-6-(4-methylthiophen-2-yl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CC1=CC(=NO1)CN1C(NC2=NC=C(C=C21)C=1SC=C(C=1)C)=O BKNYUJKUJILMNO-UHFFFAOYSA-N 0.000 claims 1
• KJGVZHVOBOKEFT-UHFFFAOYSA-N 1-[(5-methyl-1,2-oxazol-3-yl)methyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CC1=CC(=NO1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O KJGVZHVOBOKEFT-UHFFFAOYSA-N 0.000 claims 1
• MOIXXJOMFACPIG-UHFFFAOYSA-N 1-[(5-methyl-1,2-oxazol-3-yl)methyl]-6-phenyl-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CC1=CC(=NO1)CN1C(NC2=NC=C(C=C21)C1=CC=CC=C1)=O MOIXXJOMFACPIG-UHFFFAOYSA-N 0.000 claims 1
• FHGNVNGHYFDYNH-UHFFFAOYSA-N 1-[(5-methylpyridin-3-yl)methyl]-6-(3,4,5-trifluorophenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CC=1C=C(C=NC=1)CN1C(NC2=NC=C(C=C21)C1=CC(=C(C(=C1)F)F)F)=O FHGNVNGHYFDYNH-UHFFFAOYSA-N 0.000 claims 1
• QNFNYQLKIQIFMG-UHFFFAOYSA-N 1-[(5-methylpyridin-3-yl)methyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CC=1C=C(C=NC=1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O QNFNYQLKIQIFMG-UHFFFAOYSA-N 0.000 claims 1
• RZVZJGNVHRVXPX-UHFFFAOYSA-N 1-[(6-fluoropyridin-3-yl)methyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=CC=C(C=N1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O RZVZJGNVHRVXPX-UHFFFAOYSA-N 0.000 claims 1
• IZMBFGADHVKZGQ-UHFFFAOYSA-N 1-[(6-methoxypyridazin-3-yl)methyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound COC1=CC=C(N=N1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O IZMBFGADHVKZGQ-UHFFFAOYSA-N 0.000 claims 1
• QGGPVYGSBJRQLE-UHFFFAOYSA-N 1-[(6-methoxypyridin-3-yl)methyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound COC1=CC=C(C=N1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O QGGPVYGSBJRQLE-UHFFFAOYSA-N 0.000 claims 1
• VVJJLESIRGZUBF-UHFFFAOYSA-N 1-[(6-methylpyridin-3-yl)methyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CC1=CC=C(C=N1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O VVJJLESIRGZUBF-UHFFFAOYSA-N 0.000 claims 1
• FJJNJGQUPSRQFZ-UHFFFAOYSA-N 1-[(6-oxo-1H-pyridin-3-yl)methyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound O=C1C=CC(=CN1)CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O FJJNJGQUPSRQFZ-UHFFFAOYSA-N 0.000 claims 1
• AZYVONBJNRBHMF-UHFFFAOYSA-N 1-[2-(2,6-diazaspiro[3.3]heptan-2-yl)-2-oxoethyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound C1NCC11CN(C1)C(CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O)=O AZYVONBJNRBHMF-UHFFFAOYSA-N 0.000 claims 1
• LTXJHGWRFQTURD-UHFFFAOYSA-N 1-[2-(3,3-difluoroazetidin-1-yl)-2-oxoethyl]-3-methyl-6-(3-methylphenyl)imidazo[4,5-b]pyridin-2-one Chemical compound FC1(CN(C1)C(CN1C(N(C2=NC=C(C=C21)C=1C=C(C=CC=1)C)C)=O)=O)F LTXJHGWRFQTURD-UHFFFAOYSA-N 0.000 claims 1
• SLWHODSCECOQPW-UHFFFAOYSA-N 1-[2-(3,3-difluoroazetidin-1-yl)-2-oxoethyl]-3-methyl-6-[3-(trifluoromethyl)phenyl]imidazo[4,5-b]pyridin-2-one Chemical compound FC1(CN(C1)C(CN1C(N(C2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)C)=O)=O)F SLWHODSCECOQPW-UHFFFAOYSA-N 0.000 claims 1
• UGSOVYIFNFDCSB-UHFFFAOYSA-N 1-[2-(3,3-difluoroazetidin-1-yl)-2-oxoethyl]-3-methyl-6-[5-(trifluoromethyl)thiophen-2-yl]imidazo[4,5-b]pyridin-2-one Chemical compound FC1(CN(C1)C(CN1C(N(C2=NC=C(C=C21)C=1SC(=CC=1)C(F)(F)F)C)=O)=O)F UGSOVYIFNFDCSB-UHFFFAOYSA-N 0.000 claims 1
• JUTPYHATFOVNMC-UHFFFAOYSA-N 1-[2-(3,3-difluoroazetidin-1-yl)-2-oxoethyl]-6-(2-fluoro-3-methylphenyl)-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound FC1(CN(C1)C(CN1C(N(C2=NC=C(C=C21)C1=C(C(=CC=C1)C)F)C)=O)=O)F JUTPYHATFOVNMC-UHFFFAOYSA-N 0.000 claims 1
• NWSJEBMCYNVWKN-UHFFFAOYSA-N 1-[2-(3,3-difluoroazetidin-1-yl)-2-oxoethyl]-6-(3,4-difluorophenyl)-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound FC1(CN(C1)C(CN1C(N(C2=NC=C(C=C21)C1=CC(=C(C=C1)F)F)C)=O)=O)F NWSJEBMCYNVWKN-UHFFFAOYSA-N 0.000 claims 1
• MTSDPZHXQKADDH-UHFFFAOYSA-N 1-[2-(3,3-difluoroazetidin-1-yl)-2-oxoethyl]-6-(3-fluorophenyl)-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound FC1(CN(C1)C(CN1C(N(C2=NC=C(C=C21)C1=CC(=CC=C1)F)C)=O)=O)F MTSDPZHXQKADDH-UHFFFAOYSA-N 0.000 claims 1
• WZNXENIORLUKLM-UHFFFAOYSA-N 1-[2-(3,3-difluoroazetidin-1-yl)-2-oxoethyl]-6-(3-methylphenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1(CN(C1)C(CN1C(NC2=NC=C(C=C21)C=1C=C(C=CC=1)C)=O)=O)F WZNXENIORLUKLM-UHFFFAOYSA-N 0.000 claims 1
• NBXNOABBRFBTRE-UHFFFAOYSA-N 1-[2-(3,3-difluoroazetidin-1-yl)-2-oxoethyl]-6-(4-fluoro-3-methylphenyl)-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound FC1(CN(C1)C(CN1C(N(C2=NC=C(C=C21)C1=CC(=C(C=C1)F)C)C)=O)=O)F NBXNOABBRFBTRE-UHFFFAOYSA-N 0.000 claims 1
• SAIWFWYKRTXNCD-UHFFFAOYSA-N 1-[2-(3,3-difluoroazetidin-1-yl)-2-oxoethyl]-6-[3-(difluoromethoxy)-4-fluorophenyl]-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound FC1(CN(C1)C(CN1C(N(C2=NC=C(C=C21)C1=CC(=C(C=C1)F)OC(F)F)C)=O)=O)F SAIWFWYKRTXNCD-UHFFFAOYSA-N 0.000 claims 1
• XENKVFPNHPYUKN-UHFFFAOYSA-N 1-[2-(3,3-difluoroazetidin-1-yl)-2-oxoethyl]-6-[3-(difluoromethyl)-4-fluorophenyl]-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound FC1(CN(C1)C(CN1C(N(C2=NC=C(C=C21)C1=CC(=C(C=C1)F)C(F)F)C)=O)=O)F XENKVFPNHPYUKN-UHFFFAOYSA-N 0.000 claims 1
• LNDACFPZDAFGEZ-UHFFFAOYSA-N 1-[2-(3,3-difluoroazetidin-1-yl)-2-oxoethyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1(CN(C1)C(CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O)=O)F LNDACFPZDAFGEZ-UHFFFAOYSA-N 0.000 claims 1
• BMIRSLDQJVAZHP-UHFFFAOYSA-N 1-[2-(3,3-difluoroazetidin-1-yl)ethyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1(CN(C1)CCN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O)F BMIRSLDQJVAZHP-UHFFFAOYSA-N 0.000 claims 1
• VEJHHFLQLFOIRS-UHFFFAOYSA-N 1-[2-(3,3-difluoropyrrolidin-1-yl)-2-oxoethyl]-3-methyl-6-[3-(trifluoromethyl)phenyl]imidazo[4,5-b]pyridin-2-one Chemical compound FC1(CN(CC1)C(CN1C(N(C2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)C)=O)=O)F VEJHHFLQLFOIRS-UHFFFAOYSA-N 0.000 claims 1
• DAKAFYSCNJQWLF-UHFFFAOYSA-N 1-[2-(3-fluoroazetidin-1-yl)-2-oxoethyl]-3-methyl-6-(2-methyl-1,3-thiazol-5-yl)imidazo[4,5-b]pyridin-2-one Chemical compound FC1CN(C1)C(CN1C(N(C2=NC=C(C=C21)C1=CN=C(S1)C)C)=O)=O DAKAFYSCNJQWLF-UHFFFAOYSA-N 0.000 claims 1
• WNNJJXBFCBLFPH-UHFFFAOYSA-N 1-[2-(3-fluoroazetidin-1-yl)-2-oxoethyl]-3-methyl-6-(4-methyl-1,3-thiazol-2-yl)imidazo[4,5-b]pyridin-2-one Chemical compound FC1CN(C1)C(CN1C(N(C2=NC=C(C=C21)C=1SC=C(N=1)C)C)=O)=O WNNJJXBFCBLFPH-UHFFFAOYSA-N 0.000 claims 1
• RQZPLXUUHUCNHE-UHFFFAOYSA-N 1-[2-(3-fluoroazetidin-1-yl)-2-oxoethyl]-3-methyl-6-[2-(trifluoromethyl)-1,3-thiazol-4-yl]imidazo[4,5-b]pyridin-2-one Chemical compound FC1CN(C1)C(CN1C(N(C2=NC=C(C=C21)C=1N=C(SC=1)C(F)(F)F)C)=O)=O RQZPLXUUHUCNHE-UHFFFAOYSA-N 0.000 claims 1
• LGVCVJBMGKYUEW-UHFFFAOYSA-N 1-[2-(3-fluoroazetidin-1-yl)-2-oxoethyl]-3-methyl-6-[2-(trifluoromethyl)-1,3-thiazol-5-yl]imidazo[4,5-b]pyridin-2-one Chemical compound FC1CN(C1)C(CN1C(N(C2=NC=C(C=C21)C1=CN=C(S1)C(F)(F)F)C)=O)=O LGVCVJBMGKYUEW-UHFFFAOYSA-N 0.000 claims 1
• DHCZBEZBUKUAQZ-UHFFFAOYSA-N 1-[2-(3-fluoroazetidin-1-yl)-2-oxoethyl]-3-methyl-6-[2-(trifluoromethyl)thiophen-3-yl]imidazo[4,5-b]pyridin-2-one Chemical compound FC1CN(C1)C(CN1C(N(C2=NC=C(C=C21)C1=C(SC=C1)C(F)(F)F)C)=O)=O DHCZBEZBUKUAQZ-UHFFFAOYSA-N 0.000 claims 1
• DOCHLUJBYYUVPG-UHFFFAOYSA-N 1-[2-(3-fluoroazetidin-1-yl)-2-oxoethyl]-3-methyl-6-[5-(trifluoromethyl)thiophen-2-yl]imidazo[4,5-b]pyridin-2-one Chemical compound FC1CN(C1)C(CN1C(N(C2=NC=C(C=C21)C=1SC(=CC=1)C(F)(F)F)C)=O)=O DOCHLUJBYYUVPG-UHFFFAOYSA-N 0.000 claims 1
• FIBXSIZCDNDBDP-UHFFFAOYSA-N 1-[2-(3-fluoroazetidin-1-yl)-2-oxoethyl]-3-methyl-6-[5-(trifluoromethyl)thiophen-3-yl]imidazo[4,5-b]pyridin-2-one Chemical compound FC1CN(C1)C(CN1C(N(C2=NC=C(C=C21)C1=CSC(=C1)C(F)(F)F)C)=O)=O FIBXSIZCDNDBDP-UHFFFAOYSA-N 0.000 claims 1
• JXZDZNLIRKIPAG-UHFFFAOYSA-N 1-[2-(3-fluoroazetidin-1-yl)-2-oxoethyl]-6-(4-fluoro-3-methylphenyl)-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound FC1CN(C1)C(CN1C(N(C2=NC=C(C=C21)C1=CC(=C(C=C1)F)C)C)=O)=O JXZDZNLIRKIPAG-UHFFFAOYSA-N 0.000 claims 1
• FGFCASMMJUWFQC-UHFFFAOYSA-N 1-[2-(3-fluoroazetidin-1-yl)-2-oxoethyl]-6-(5-fluorothiophen-2-yl)-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound FC1CN(C1)C(CN1C(N(C2=NC=C(C=C21)C=1SC(=CC=1)F)C)=O)=O FGFCASMMJUWFQC-UHFFFAOYSA-N 0.000 claims 1
• FDLIKLKMLSBNAT-UHFFFAOYSA-N 1-[2-(3-fluoroazetidin-1-yl)-2-oxoethyl]-6-[5-(hydroxymethyl)thiophen-2-yl]-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound FC1CN(C1)C(CN1C(N(C2=NC=C(C=C21)C=1SC(=CC=1)CO)C)=O)=O FDLIKLKMLSBNAT-UHFFFAOYSA-N 0.000 claims 1
• CUSFQDKHTGPAEB-UHFFFAOYSA-N 1-[2-(3-fluoroazetidin-1-yl)-2-oxoethyl]-6-[5-(trifluoromethyl)thiophen-2-yl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1CN(C1)C(CN1C(NC2=NC=C(C=C21)C=1SC(=CC=1)C(F)(F)F)=O)=O CUSFQDKHTGPAEB-UHFFFAOYSA-N 0.000 claims 1
• FCNCYSBXQOYJQO-UHFFFAOYSA-N 1-[2-(3-fluoroazetidin-1-yl)ethyl]-6-(2-methylphenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1CN(C1)CCN1C(NC2=NC=C(C=C21)C1=C(C=CC=C1)C)=O FCNCYSBXQOYJQO-UHFFFAOYSA-N 0.000 claims 1
• ZNUQBQOSWLAIGB-UHFFFAOYSA-N 1-[2-(3-fluoroazetidin-1-yl)ethyl]-6-(4-fluoro-2,3-dimethylphenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1CN(C1)CCN1C(NC2=NC=C(C=C21)C1=C(C(=C(C=C1)F)C)C)=O ZNUQBQOSWLAIGB-UHFFFAOYSA-N 0.000 claims 1
• HYVUXILHYMTNMK-UHFFFAOYSA-N 1-[2-(3-fluoroazetidin-1-yl)ethyl]-6-(4-fluoro-2-methylphenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1CN(C1)CCN1C(NC2=NC=C(C=C21)C1=C(C=C(C=C1)F)C)=O HYVUXILHYMTNMK-UHFFFAOYSA-N 0.000 claims 1
• BQBRVEUTMPWXMP-UHFFFAOYSA-N 1-[2-(3-fluoroazetidin-1-yl)ethyl]-6-[2-methyl-3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1CN(C1)CCN1C(NC2=NC=C(C=C21)C1=C(C(=CC=C1)C(F)(F)F)C)=O BQBRVEUTMPWXMP-UHFFFAOYSA-N 0.000 claims 1
• RAGWSAJIXZDTMW-UHFFFAOYSA-N 1-[2-(3-fluoroazetidin-1-yl)ethyl]-6-[2-methyl-5-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1CN(C1)CCN1C(NC2=NC=C(C=C21)C1=C(C=CC(=C1)C(F)(F)F)C)=O RAGWSAJIXZDTMW-UHFFFAOYSA-N 0.000 claims 1
• JYHHOTUSZKRFFS-UHFFFAOYSA-N 1-[2-(3-fluoroazetidin-1-yl)ethyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1CN(C1)CCN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O JYHHOTUSZKRFFS-UHFFFAOYSA-N 0.000 claims 1
• JKHXFVPGQUIIBY-UHFFFAOYSA-N 1-[2-(3-fluoroazetidin-1-yl)ethyl]-6-phenyl-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1CN(C1)CCN1C(NC2=NC=C(C=C21)C1=CC=CC=C1)=O JKHXFVPGQUIIBY-UHFFFAOYSA-N 0.000 claims 1
• LPEOHUUDHUKDIA-UHFFFAOYSA-N 1-[2-(3-hydroxy-3-methylazetidin-1-yl)-2-oxoethyl]-6-(5-methylpyridin-3-yl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound OC1(CN(C1)C(CN1C(NC2=NC=C(C=C21)C=1C=NC=C(C=1)C)=O)=O)C LPEOHUUDHUKDIA-UHFFFAOYSA-N 0.000 claims 1
• ISHJDEVVXUCWSC-UHFFFAOYSA-N 1-[2-(3-hydroxyazetidin-1-yl)ethyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound OC1CN(C1)CCN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O ISHJDEVVXUCWSC-UHFFFAOYSA-N 0.000 claims 1
• PTPDSZKFEBUNEZ-UHFFFAOYSA-N 1-[2-(3-methoxyazetidin-1-yl)-2-oxoethyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound COC1CN(C1)C(CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O)=O PTPDSZKFEBUNEZ-UHFFFAOYSA-N 0.000 claims 1
• YLTSVMAGRVVAEP-UHFFFAOYSA-N 1-[2-(3-methoxyazetidin-1-yl)ethyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound COC1CN(C1)CCN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O YLTSVMAGRVVAEP-UHFFFAOYSA-N 0.000 claims 1
• MRBYKIXGXZDMMG-UHFFFAOYSA-N 1-[2-(3-methylazetidin-1-yl)-2-oxoethyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CC1CN(C1)C(CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O)=O MRBYKIXGXZDMMG-UHFFFAOYSA-N 0.000 claims 1
• JHUWWJOXVUZUEU-UHFFFAOYSA-N 1-[2-(3-methylpyrrolidin-1-yl)ethyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CC1CN(CC1)CCN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O JHUWWJOXVUZUEU-UHFFFAOYSA-N 0.000 claims 1
• AXLCXEXFZROUAT-UHFFFAOYSA-N 1-[2-(4-fluoropiperidin-1-yl)ethyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1CCN(CC1)CCN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O AXLCXEXFZROUAT-UHFFFAOYSA-N 0.000 claims 1
• STCYVLKROSFGBR-UHFFFAOYSA-N 1-[2-(4-hydroxypiperidin-1-yl)ethyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound OC1CCN(CC1)CCN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O STCYVLKROSFGBR-UHFFFAOYSA-N 0.000 claims 1
• QEDMESBXMMCILX-UHFFFAOYSA-N 1-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CN1CCN(CC1)C(CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O)=O QEDMESBXMMCILX-UHFFFAOYSA-N 0.000 claims 1
• KWPJJMAUEQTPMK-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-3-(2-fluoroethyl)-6-[5-(trifluoromethyl)thiophen-2-yl]imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(N(C2=NC=C(C=C21)C=1SC(=CC=1)C(F)(F)F)CCF)=O)=O KWPJJMAUEQTPMK-UHFFFAOYSA-N 0.000 claims 1
• BIPXWRFXYDZVCH-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-3-(fluoromethyl)-6-[5-(trifluoromethyl)thiophen-2-yl]imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(N(C2=NC=C(C=C21)C=1SC(=CC=1)C(F)(F)F)CF)=O)=O BIPXWRFXYDZVCH-UHFFFAOYSA-N 0.000 claims 1
• IOUDFLGTXMIKJN-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-3-methyl-6-(2-methyl-1,3-thiazol-5-yl)imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(N(C2=NC=C(C=C21)C1=CN=C(S1)C)C)=O)=O IOUDFLGTXMIKJN-UHFFFAOYSA-N 0.000 claims 1
• LJPJRZZUZDMNHH-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-3-methyl-6-(3,4,5-trifluorophenyl)imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(N(C2=NC=C(C=C21)C1=CC(=C(C(=C1)F)F)F)C)=O)=O LJPJRZZUZDMNHH-UHFFFAOYSA-N 0.000 claims 1
• TXJXBHIKBDZABF-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-3-methyl-6-(5-methylthiophen-2-yl)imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(N(C2=NC=C(C=C21)C=1SC(=CC=1)C)C)=O)=O TXJXBHIKBDZABF-UHFFFAOYSA-N 0.000 claims 1
• JCJHXWKGJMLDFE-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-3-methyl-6-[2-(trifluoromethyl)-1,3-thiazol-5-yl]imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(N(C2=NC=C(C=C21)C1=CN=C(S1)C(F)(F)F)C)=O)=O JCJHXWKGJMLDFE-UHFFFAOYSA-N 0.000 claims 1
• QOJFSZSTBJRURG-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-3-methyl-6-[2-(trifluoromethyl)thiophen-3-yl]imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(N(C2=NC=C(C=C21)C1=C(SC=C1)C(F)(F)F)C)=O)=O QOJFSZSTBJRURG-UHFFFAOYSA-N 0.000 claims 1
• VVCQDRNWNYRURE-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-3-methyl-6-[5-(1,1,2,2,2-pentafluoroethyl)thiophen-2-yl]imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(N(C2=NC=C(C=C21)C=1SC(=CC=1)C(C(F)(F)F)(F)F)C)=O)=O VVCQDRNWNYRURE-UHFFFAOYSA-N 0.000 claims 1
• GHHIIQKNBPUFCX-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-3-methyl-6-[5-(trifluoromethyl)thiophen-3-yl]imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(N(C2=NC=C(C=C21)C1=CSC(=C1)C(F)(F)F)C)=O)=O GHHIIQKNBPUFCX-UHFFFAOYSA-N 0.000 claims 1
• HAIWAOFUMPARPL-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-6-(2,4-difluoro-3-methylphenyl)-3-(fluoromethyl)imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(N(C2=NC=C(C=C21)C1=C(C(=C(C=C1)F)C)F)CF)=O)=O HAIWAOFUMPARPL-UHFFFAOYSA-N 0.000 claims 1
• MSRCCIJEUIUHKR-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-6-(2,4-difluoro-3-methylphenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(NC2=NC=C(C=C21)C1=C(C(=C(C=C1)F)C)F)=O)=O MSRCCIJEUIUHKR-UHFFFAOYSA-N 0.000 claims 1
• KTIDKZVGQFVWGD-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-6-(3,4-difluorophenyl)-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(N(C2=NC=C(C=C21)C1=CC(=C(C=C1)F)F)C)=O)=O KTIDKZVGQFVWGD-UHFFFAOYSA-N 0.000 claims 1
• RLTQVLZBEQGICU-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-6-(3,5-difluorophenyl)-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(N(C2=NC=C(C=C21)C1=CC(=CC(=C1)F)F)C)=O)=O RLTQVLZBEQGICU-UHFFFAOYSA-N 0.000 claims 1
• KCXVNIRJNKSVFN-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-6-(4-fluoro-2-methylphenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(NC2=NC=C(C=C21)C1=C(C=C(C=C1)F)C)=O)=O KCXVNIRJNKSVFN-UHFFFAOYSA-N 0.000 claims 1
• PJELBWFBQFHVSN-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-6-(5-chloro-4-methylthiophen-2-yl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(NC2=NC=C(C=C21)C=1SC(=C(C=1)C)Cl)=O)=O PJELBWFBQFHVSN-UHFFFAOYSA-N 0.000 claims 1
• HNUVIOQQXNIRMU-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-6-(5-ethylthiophen-2-yl)-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(N(C2=NC=C(C=C21)C=1SC(=CC=1)CC)C)=O)=O HNUVIOQQXNIRMU-UHFFFAOYSA-N 0.000 claims 1
• APXQQZMKKRAENC-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-6-(5-fluorothiophen-2-yl)-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(N(C2=NC=C(C=C21)C=1SC(=CC=1)F)C)=O)=O APXQQZMKKRAENC-UHFFFAOYSA-N 0.000 claims 1
• HMOADCKOQNPPLY-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-6-(6-fluoropyridin-3-yl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(NC2=NC=C(C=C21)C=1C=NC(=CC=1)F)=O)=O HMOADCKOQNPPLY-UHFFFAOYSA-N 0.000 claims 1
• ABMLOYDHKOLWIS-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-6-[2-methyl-3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(NC2=NC=C(C=C21)C1=C(C(=CC=C1)C(F)(F)F)C)=O)=O ABMLOYDHKOLWIS-UHFFFAOYSA-N 0.000 claims 1
• XMJPUVYLGKKTNM-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-6-[2-methyl-5-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(NC2=NC=C(C=C21)C1=C(C=CC(=C1)C(F)(F)F)C)=O)=O XMJPUVYLGKKTNM-UHFFFAOYSA-N 0.000 claims 1
• OHOGPOUYKUXAHL-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-6-[3-(2-fluoroethoxy)-5-(trifluoromethyl)phenyl]-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(N(C2=NC=C(C=C21)C1=CC(=CC(=C1)C(F)(F)F)OCCF)C)=O)=O OHOGPOUYKUXAHL-UHFFFAOYSA-N 0.000 claims 1
• WMIBMWDMMZPQRG-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-6-[3-(2-fluoroethoxy)-5-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(NC2=NC=C(C=C21)C1=CC(=CC(=C1)C(F)(F)F)OCCF)=O)=O WMIBMWDMMZPQRG-UHFFFAOYSA-N 0.000 claims 1
• JEJIBWJJCWXPTN-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-6-[3-(difluoromethoxy)-4-fluorophenyl]-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(N(C2=NC=C(C=C21)C1=CC(=C(C=C1)F)OC(F)F)C)=O)=O JEJIBWJJCWXPTN-UHFFFAOYSA-N 0.000 claims 1
• KBMHIIGNNRUHMZ-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-6-[3-(difluoromethyl)-4-fluorophenyl]-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(N(C2=NC=C(C=C21)C1=CC(=C(C=C1)F)C(F)F)C)=O)=O KBMHIIGNNRUHMZ-UHFFFAOYSA-N 0.000 claims 1
• RDFSOSDDMGDNNO-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O)=O RDFSOSDDMGDNNO-UHFFFAOYSA-N 0.000 claims 1
• KYHRJXXSXHLIHG-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-6-[4-(2-fluoroethoxy)-3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(NC2=NC=C(C=C21)C1=CC(=C(C=C1)OCCF)C(F)(F)F)=O)=O KYHRJXXSXHLIHG-UHFFFAOYSA-N 0.000 claims 1
• UHUIEJUQWSPSJU-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-6-[4-(difluoromethyl)thiophen-2-yl]-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(N(C2=NC=C(C=C21)C=1SC=C(C=1)C(F)F)C)=O)=O UHUIEJUQWSPSJU-UHFFFAOYSA-N 0.000 claims 1
• ZJVPWGFTQATRRK-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-6-[4-chloro-3-(difluoromethoxy)phenyl]-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(N(C2=NC=C(C=C21)C1=CC(=C(C=C1)Cl)OC(F)F)C)=O)=O ZJVPWGFTQATRRK-UHFFFAOYSA-N 0.000 claims 1
• KTDMNJGDTMUKDB-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-6-[5-(difluoromethyl)thiophen-2-yl]-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(N(C2=NC=C(C=C21)C=1SC(=CC=1)C(F)F)C)=O)=O KTDMNJGDTMUKDB-UHFFFAOYSA-N 0.000 claims 1
• LPHRRZNXDQWBBH-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-6-[5-(difluoromethyl)thiophen-3-yl]-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(N(C2=NC=C(C=C21)C1=CSC(=C1)C(F)F)C)=O)=O LPHRRZNXDQWBBH-UHFFFAOYSA-N 0.000 claims 1
• KEQOTBTUVWZKPQ-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-2-oxoethyl]-6-[5-(hydroxymethyl)thiophen-2-yl]-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)C(CN1C(N(C2=NC=C(C=C21)C=1SC(=CC=1)CO)C)=O)=O KEQOTBTUVWZKPQ-UHFFFAOYSA-N 0.000 claims 1
• XWPZFKHGTYKVCL-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)ethyl]-3-methyl-6-[3-(trifluoromethyl)phenyl]imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)CCN1C(N(C2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)C)=O XWPZFKHGTYKVCL-UHFFFAOYSA-N 0.000 claims 1
• BAAKNGLAUGFORE-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)ethyl]-6-(2,3-dimethylphenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)CCN1C(NC2=NC=C(C=C21)C1=C(C(=CC=C1)C)C)=O BAAKNGLAUGFORE-UHFFFAOYSA-N 0.000 claims 1
• YUZQKXJADPMFRX-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)ethyl]-6-(2,6-dimethylphenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)CCN1C(NC2=NC=C(C=C21)C1=C(C=CC=C1C)C)=O YUZQKXJADPMFRX-UHFFFAOYSA-N 0.000 claims 1
• GELARFPHFFBIMQ-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)ethyl]-6-(3,5-difluorophenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)CCN1C(NC2=NC=C(C=C21)C1=CC(=CC(=C1)F)F)=O GELARFPHFFBIMQ-UHFFFAOYSA-N 0.000 claims 1
• IXCCFMHPHIJVCW-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)ethyl]-6-(3-chlorophenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)CCN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)Cl)=O IXCCFMHPHIJVCW-UHFFFAOYSA-N 0.000 claims 1
• WNQORPZEWWSSDO-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)ethyl]-6-(3-methylphenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)CCN1C(NC2=NC=C(C=C21)C=1C=C(C=CC=1)C)=O WNQORPZEWWSSDO-UHFFFAOYSA-N 0.000 claims 1
• QBWXAZAEDHZIGX-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)ethyl]-6-(4-fluoro-2,3-dimethylphenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)CCN1C(NC2=NC=C(C=C21)C1=C(C(=C(C=C1)F)C)C)=O QBWXAZAEDHZIGX-UHFFFAOYSA-N 0.000 claims 1
• VPTXKSSRQKRRBF-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)ethyl]-6-(4-fluoro-2-methylphenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)CCN1C(NC2=NC=C(C=C21)C1=C(C=C(C=C1)F)C)=O VPTXKSSRQKRRBF-UHFFFAOYSA-N 0.000 claims 1
• JIYGIBZQYHLRHY-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)ethyl]-6-(4-fluoro-3-methylphenyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)CCN1C(NC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C)=O JIYGIBZQYHLRHY-UHFFFAOYSA-N 0.000 claims 1
• JDJOWMIMSGTFII-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)ethyl]-6-[2-(trifluoromethyl)pyridin-4-yl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)CCN1C(NC2=NC=C(C=C21)C1=CC(=NC=C1)C(F)(F)F)=O JDJOWMIMSGTFII-UHFFFAOYSA-N 0.000 claims 1
• CKIOQBHDVRUKHV-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)ethyl]-6-[2-methyl-3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)CCN1C(NC2=NC=C(C=C21)C1=C(C(=CC=C1)C(F)(F)F)C)=O CKIOQBHDVRUKHV-UHFFFAOYSA-N 0.000 claims 1
• PEAOVRUTHAMIAK-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)ethyl]-6-[2-methyl-5-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)CCN1C(NC2=NC=C(C=C21)C1=C(C=CC(=C1)C(F)(F)F)C)=O PEAOVRUTHAMIAK-UHFFFAOYSA-N 0.000 claims 1
• HKIREWARSNPDMB-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)ethyl]-6-[3-(trifluoromethoxy)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)CCN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)OC(F)(F)F)=O HKIREWARSNPDMB-UHFFFAOYSA-N 0.000 claims 1
• DLIIWNNAACMMGL-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)ethyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)CCN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O DLIIWNNAACMMGL-UHFFFAOYSA-N 0.000 claims 1
• QVJAQSWMENCSTB-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)ethyl]-6-phenyl-3H-imidazo[4,5-b]pyridin-2-one Chemical compound N1(CCC1)CCN1C(NC2=NC=C(C=C21)C1=CC=CC=C1)=O QVJAQSWMENCSTB-UHFFFAOYSA-N 0.000 claims 1
• KDVQLHFASINJIB-UHFFFAOYSA-N 1-[2-(cyclopropylamino)ethyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound C1(CC1)NCCN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O KDVQLHFASINJIB-UHFFFAOYSA-N 0.000 claims 1
• GYROTQLCGSWSJW-UHFFFAOYSA-N 1-[2-[2-oxo-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-1-yl]acetyl]azetidine-3-carbonitrile Chemical compound O=C1N(C=2C(=NC=C(C=2)C2=CC(=CC=C2)C(F)(F)F)N1)CC(=O)N1CC(C1)C#N GYROTQLCGSWSJW-UHFFFAOYSA-N 0.000 claims 1
• NMWJXIMCNAUSSH-UHFFFAOYSA-N 1-[2-[3-(2-fluoroethyl)azetidin-1-yl]-2-oxoethyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FCCC1CN(C1)C(CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O)=O NMWJXIMCNAUSSH-UHFFFAOYSA-N 0.000 claims 1
• SFSIVWWNRMDJRJ-UHFFFAOYSA-N 1-[2-[3-(methoxymethyl)azetidin-1-yl]-2-oxoethyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound COCC1CN(C1)C(CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O)=O SFSIVWWNRMDJRJ-UHFFFAOYSA-N 0.000 claims 1
• PTTCCUHNWGJCMH-UHFFFAOYSA-N 1-[2-[3-(trifluoromethyl)azetidin-1-yl]ethyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC(C1CN(C1)CCN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O)(F)F PTTCCUHNWGJCMH-UHFFFAOYSA-N 0.000 claims 1
• ZAORVOVKLRCVFJ-UHFFFAOYSA-N 1-[2-oxo-2-(1,3-thiazol-2-yl)ethyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound O=C(CN1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O)C=1SC=CN=1 ZAORVOVKLRCVFJ-UHFFFAOYSA-N 0.000 claims 1
• LYAQGBFZDHGDNN-CYBMUJFWSA-N 1-[[(2R)-oxetan-2-yl]methyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC(F)(F)c1cccc(c1)-c1cnc2[nH]c(=O)n(C[C@H]3CCO3)c2c1 LYAQGBFZDHGDNN-CYBMUJFWSA-N 0.000 claims 1
• LYAQGBFZDHGDNN-ZDUSSCGKSA-N 1-[[(2S)-oxetan-2-yl]methyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC(F)(F)c1cccc(c1)-c1cnc2[nH]c(=O)n(C[C@@H]3CCO3)c2c1 LYAQGBFZDHGDNN-ZDUSSCGKSA-N 0.000 claims 1
• GXCCBGPYQPWWNV-UHFFFAOYSA-N 1-[difluoro(pyridin-3-yl)methyl]-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC(N1C(NC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O)(C=1C=NC=CC=1)F GXCCBGPYQPWWNV-UHFFFAOYSA-N 0.000 claims 1
• FRFQXMDVLFBDHW-UHFFFAOYSA-N 1-benzyl-6-[4-fluoro-3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound C(C1=CC=CC=C1)N1C(NC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C(F)(F)F)=O FRFQXMDVLFBDHW-UHFFFAOYSA-N 0.000 claims 1
• WGSXKYXKAARAKD-UHFFFAOYSA-N 1-fluoro-3-isocyanato-5-(trifluoromethyl)benzene Chemical group FC1=CC(N=C=O)=CC(C(F)(F)F)=C1 WGSXKYXKAARAKD-UHFFFAOYSA-N 0.000 claims 1
• SLYBMTRTNJKHKT-UHFFFAOYSA-N 2-[2-oxo-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-1-yl]-N-pyridin-2-ylacetamide Chemical compound O=C1N(C=2C(=NC=C(C=2)C2=CC(=CC=C2)C(F)(F)F)N1)CC(=O)NC1=NC=CC=C1 SLYBMTRTNJKHKT-UHFFFAOYSA-N 0.000 claims 1
• FLHNBMRGROEKIX-UHFFFAOYSA-N 2-[2-oxo-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-1-yl]acetamide Chemical compound O=C1N(C=2C(=NC=C(C=2)C2=CC(=CC=C2)C(F)(F)F)N1)CC(=O)N FLHNBMRGROEKIX-UHFFFAOYSA-N 0.000 claims 1
• ANTPIVZOHQZPBP-UHFFFAOYSA-N 2-[2-oxo-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-1-yl]acetic acid Chemical compound O=C1N(C=2C(=NC=C(C=2)C2=CC(=CC=C2)C(F)(F)F)N1)CC(=O)O ANTPIVZOHQZPBP-UHFFFAOYSA-N 0.000 claims 1
• JDVGAMHOGREECD-UHFFFAOYSA-N 2-[3-(fluoromethyl)-2-oxo-6-[5-(trifluoromethyl)thiophen-2-yl]imidazo[4,5-b]pyridin-1-yl]-N,N-dimethylacetamide Chemical compound FCN1C(N(C=2C1=NC=C(C=2)C=1SC(=CC=1)C(F)(F)F)CC(=O)N(C)C)=O JDVGAMHOGREECD-UHFFFAOYSA-N 0.000 claims 1
• SVZBSDGFIXXRSF-UHFFFAOYSA-N 2-[6-(2,3-difluorophenyl)-3-methyl-2-oxoimidazo[4,5-b]pyridin-1-yl]-N,N-dimethylacetamide Chemical compound FC1=C(C=CC=C1F)C=1C=C2C(=NC=1)N(C(N2CC(=O)N(C)C)=O)C SVZBSDGFIXXRSF-UHFFFAOYSA-N 0.000 claims 1
• GWYQRPMZDOMUSF-UHFFFAOYSA-N 2-[6-(2,4-difluoro-3-methylphenyl)-3-(fluoromethyl)-2-oxoimidazo[4,5-b]pyridin-1-yl]-N,N-dimethylacetamide Chemical compound FC1=C(C=CC(=C1C)F)C=1C=C2C(=NC=1)N(C(N2CC(=O)N(C)C)=O)CF GWYQRPMZDOMUSF-UHFFFAOYSA-N 0.000 claims 1
• AKQXPNGVJADHLE-UHFFFAOYSA-N 2-[6-(2,4-difluoro-3-methylphenyl)-3-methyl-2-oxoimidazo[4,5-b]pyridin-1-yl]-N,N-dimethylacetamide Chemical compound FC1=C(C=CC(=C1C)F)C=1C=C2C(=NC=1)N(C(N2CC(=O)N(C)C)=O)C AKQXPNGVJADHLE-UHFFFAOYSA-N 0.000 claims 1
• KZGBDKAYAXIJSS-UHFFFAOYSA-N 2-[6-(2-chloro-4-methoxyphenyl)-2-oxo-3H-imidazo[4,5-b]pyridin-1-yl]-N-cyclopropylacetamide Chemical compound ClC1=C(C=CC(=C1)OC)C=1C=C2C(=NC=1)NC(N2CC(=O)NC1CC1)=O KZGBDKAYAXIJSS-UHFFFAOYSA-N 0.000 claims 1
• FOCZQFJOZUFOCD-UHFFFAOYSA-N 2-[6-(2-ethoxy-5-fluorophenyl)-2-oxo-3H-imidazo[4,5-b]pyridin-1-yl]-N-(2-methoxyethyl)acetamide Chemical compound C(C)OC1=C(C=C(C=C1)F)C=1C=C2C(=NC=1)NC(N2CC(=O)NCCOC)=O FOCZQFJOZUFOCD-UHFFFAOYSA-N 0.000 claims 1
• AOFFKDBDSWRFKZ-UHFFFAOYSA-N 2-[6-(2-ethoxyphenyl)-2-oxo-3H-imidazo[4,5-b]pyridin-1-yl]-N-methylacetamide Chemical compound C(C)OC1=C(C=CC=C1)C=1C=C2C(=NC=1)NC(N2CC(=O)NC)=O AOFFKDBDSWRFKZ-UHFFFAOYSA-N 0.000 claims 1
• RWWJCPGNQCXYCF-UHFFFAOYSA-N 2-[6-(2-fluoro-3-methylphenyl)-3-methyl-2-oxoimidazo[4,5-b]pyridin-1-yl]-N,N-dimethylacetamide Chemical compound FC1=C(C=CC=C1C)C=1C=C2C(=NC=1)N(C(N2CC(=O)N(C)C)=O)C RWWJCPGNQCXYCF-UHFFFAOYSA-N 0.000 claims 1
• DQVOKXODALPJPQ-UHFFFAOYSA-N 2-[6-(3,4-difluorophenyl)-3-methyl-2-oxoimidazo[4,5-b]pyridin-1-yl]-N,N-dimethylacetamide Chemical compound FC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)N(C(N2CC(=O)N(C)C)=O)C DQVOKXODALPJPQ-UHFFFAOYSA-N 0.000 claims 1
• YIRITNYQQSBTBY-UHFFFAOYSA-N 2-[6-(3,5-difluorophenyl)-2-oxo-3H-imidazo[4,5-b]pyridin-1-yl]-N-(2-methoxyethyl)acetamide Chemical compound FC=1C=C(C=C(C=1)F)C=1C=C2C(=NC=1)NC(N2CC(=O)NCCOC)=O YIRITNYQQSBTBY-UHFFFAOYSA-N 0.000 claims 1
• UMVMAZYAKHQJES-UHFFFAOYSA-N 2-[6-(3,5-difluorophenyl)-3-methyl-2-oxoimidazo[4,5-b]pyridin-1-yl]-N,N-dimethylacetamide Chemical compound FC=1C=C(C=C(C=1)F)C=1C=C2C(=NC=1)N(C(N2CC(=O)N(C)C)=O)C UMVMAZYAKHQJES-UHFFFAOYSA-N 0.000 claims 1
• SCXBKHWWBGAWSW-UHFFFAOYSA-N 2-[6-(3,5-dimethylphenyl)-2-oxo-3H-imidazo[4,5-b]pyridin-1-yl]-N-methylacetamide Chemical compound CC=1C=C(C=C(C=1)C)C=1C=C2C(=NC=1)NC(N2CC(=O)NC)=O SCXBKHWWBGAWSW-UHFFFAOYSA-N 0.000 claims 1
• KWOFRIDEDUVERT-UHFFFAOYSA-N 2-[6-(3-chloro-4-fluorophenyl)-2-oxo-3H-imidazo[4,5-b]pyridin-1-yl]-N-(2-methoxyethyl)acetamide Chemical compound ClC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)NC(N2CC(=O)NCCOC)=O KWOFRIDEDUVERT-UHFFFAOYSA-N 0.000 claims 1
• GQHKPBAPXWZJIM-UHFFFAOYSA-N 2-[6-(3-chloro-4-fluorophenyl)-2-oxo-3H-imidazo[4,5-b]pyridin-1-yl]-N-cyclopropylacetamide Chemical compound ClC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)NC(N2CC(=O)NC1CC1)=O GQHKPBAPXWZJIM-UHFFFAOYSA-N 0.000 claims 1
• UYLPYPVXCJIAEP-UHFFFAOYSA-N 2-[6-(3-chloro-4-fluorophenyl)-2-oxo-3H-imidazo[4,5-b]pyridin-1-yl]acetamide Chemical compound ClC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)NC(N2CC(=O)N)=O UYLPYPVXCJIAEP-UHFFFAOYSA-N 0.000 claims 1
• XKHZJJYBLKDOLJ-UHFFFAOYSA-N 2-[6-(4-chlorophenyl)-2-oxo-3H-imidazo[4,5-b]pyridin-1-yl]-N-cyclopropylacetamide Chemical compound ClC1=CC=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC(=O)NC1CC1)=O XKHZJJYBLKDOLJ-UHFFFAOYSA-N 0.000 claims 1
• PGIUZNIPGJEIFS-UHFFFAOYSA-N 2-[6-(4-fluoro-2-methoxyphenyl)-2-oxo-3H-imidazo[4,5-b]pyridin-1-yl]-N-(2-methoxyethyl)acetamide Chemical compound FC1=CC(=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC(=O)NCCOC)=O)OC PGIUZNIPGJEIFS-UHFFFAOYSA-N 0.000 claims 1
• NTQUQHRNKMUCAT-UHFFFAOYSA-N 2-[6-(4-fluoro-2-methoxyphenyl)-2-oxo-3H-imidazo[4,5-b]pyridin-1-yl]-N-methylacetamide Chemical compound FC1=CC(=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC(=O)NC)=O)OC NTQUQHRNKMUCAT-UHFFFAOYSA-N 0.000 claims 1
• JEZYATNANUMKIR-UHFFFAOYSA-N 2-[6-(4-fluoro-2-methoxyphenyl)-2-oxo-3H-imidazo[4,5-b]pyridin-1-yl]acetamide Chemical compound FC1=CC(=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC(=O)N)=O)OC JEZYATNANUMKIR-UHFFFAOYSA-N 0.000 claims 1
• XEFSYXCDQFISCG-UHFFFAOYSA-N 2-[6-(4-fluoro-2-methylphenyl)-2-oxo-3H-imidazo[4,5-b]pyridin-1-yl]-N-methylacetamide Chemical compound FC1=CC(=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC(=O)NC)=O)C XEFSYXCDQFISCG-UHFFFAOYSA-N 0.000 claims 1
• PTZFGJICHUXACN-UHFFFAOYSA-N 2-[6-(4-methoxy-3-methylphenyl)-2-oxo-3H-imidazo[4,5-b]pyridin-1-yl]-N-methylacetamide Chemical compound COC1=C(C=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC(=O)NC)=O)C PTZFGJICHUXACN-UHFFFAOYSA-N 0.000 claims 1
• GCHXTEIDUFZVEP-UHFFFAOYSA-N 2-[6-(5-chloro-4-methylthiophen-2-yl)-3-methyl-2-oxoimidazo[4,5-b]pyridin-1-yl]-N,N-dimethylacetamide Chemical compound ClC1=C(C=C(S1)C=1C=C2C(=NC=1)N(C(N2CC(=O)N(C)C)=O)C)C GCHXTEIDUFZVEP-UHFFFAOYSA-N 0.000 claims 1
• UZJDNVUOCFAGJJ-UHFFFAOYSA-N 2-[6-(5-chlorothiophen-2-yl)-3-methyl-2-oxoimidazo[4,5-b]pyridin-1-yl]-N,N-dimethylacetamide Chemical compound ClC1=CC=C(S1)C=1C=C2C(=NC=1)N(C(N2CC(=O)N(C)C)=O)C UZJDNVUOCFAGJJ-UHFFFAOYSA-N 0.000 claims 1
• FDRRFKSBLXEOQB-UHFFFAOYSA-N 2-[6-(5-cyclopropylthiophen-2-yl)-3-methyl-2-oxoimidazo[4,5-b]pyridin-1-yl]-N,N-dimethylacetamide Chemical compound C1(CC1)C1=CC=C(S1)C=1C=C2C(=NC=1)N(C(N2CC(=O)N(C)C)=O)C FDRRFKSBLXEOQB-UHFFFAOYSA-N 0.000 claims 1
• UCYXHLIEZUUIJU-UHFFFAOYSA-N 2-[6-(5-ethylthiophen-2-yl)-3-methyl-2-oxoimidazo[4,5-b]pyridin-1-yl]-N,N-dimethylacetamide Chemical compound C(C)C1=CC=C(S1)C=1C=C2C(=NC=1)N(C(N2CC(=O)N(C)C)=O)C UCYXHLIEZUUIJU-UHFFFAOYSA-N 0.000 claims 1
• PAWRHKPXJFPOKA-UHFFFAOYSA-N 2-[6-(5-fluorothiophen-2-yl)-3-methyl-2-oxoimidazo[4,5-b]pyridin-1-yl]-N,N-dimethylacetamide Chemical compound FC1=CC=C(S1)C=1C=C2C(=NC=1)N(C(N2CC(=O)N(C)C)=O)C PAWRHKPXJFPOKA-UHFFFAOYSA-N 0.000 claims 1
• FQBOIUBNVWYOTL-UHFFFAOYSA-N 2-[6-[2-fluoro-3-(trifluoromethyl)phenyl]-3-methyl-2-oxoimidazo[4,5-b]pyridin-1-yl]-N,N-dimethylacetamide Chemical compound FC1=C(C=CC=C1C(F)(F)F)C=1C=C2C(=NC=1)N(C(N2CC(=O)N(C)C)=O)C FQBOIUBNVWYOTL-UHFFFAOYSA-N 0.000 claims 1
• QBYNDVLYJBBLCO-UHFFFAOYSA-N 2-[6-[3,4-difluoro-5-(trifluoromethyl)phenyl]-3-methyl-2-oxoimidazo[4,5-b]pyridin-1-yl]-N,N-dimethylacetamide Chemical compound FC=1C=C(C=C(C=1F)C(F)(F)F)C=1C=C2C(=NC=1)N(C(N2CC(=O)N(C)C)=O)C QBYNDVLYJBBLCO-UHFFFAOYSA-N 0.000 claims 1
• UITVTZNVMBJANK-UHFFFAOYSA-N 2-[6-[3-(difluoromethoxy)-4-fluorophenyl]-3-methyl-2-oxoimidazo[4,5-b]pyridin-1-yl]-N,N-dimethylacetamide Chemical compound FC(OC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)N(C(N2CC(=O)N(C)C)=O)C)F UITVTZNVMBJANK-UHFFFAOYSA-N 0.000 claims 1
• PWLGLCFRIPHQAO-UHFFFAOYSA-N 2-[6-[3-(difluoromethyl)-4-fluorophenyl]-3-methyl-2-oxoimidazo[4,5-b]pyridin-1-yl]-N,N-dimethylacetamide Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)N(C(N2CC(=O)N(C)C)=O)C)F PWLGLCFRIPHQAO-UHFFFAOYSA-N 0.000 claims 1
• ZMZYUZTXEXMVIS-UHFFFAOYSA-N 2-[6-[3-(difluoromethyl)phenyl]-3-methyl-2-oxoimidazo[4,5-b]pyridin-1-yl]-N,N-dimethylacetamide Chemical compound FC(C=1C=C(C=CC=1)C=1C=C2C(=NC=1)N(C(N2CC(=O)N(C)C)=O)C)F ZMZYUZTXEXMVIS-UHFFFAOYSA-N 0.000 claims 1
• XRTJZYNFNJZTAX-UHFFFAOYSA-N 2-[6-[4-chloro-3-(difluoromethoxy)phenyl]-3-methyl-2-oxoimidazo[4,5-b]pyridin-1-yl]-N,N-dimethylacetamide Chemical compound ClC1=C(C=C(C=C1)C=1C=C2C(=NC=1)N(C(N2CC(=O)N(C)C)=O)C)OC(F)F XRTJZYNFNJZTAX-UHFFFAOYSA-N 0.000 claims 1
• VMNLQDPQMDGDRZ-UHFFFAOYSA-N 2-[6-[5-(difluoromethyl)thiophen-2-yl]-3-methyl-2-oxoimidazo[4,5-b]pyridin-1-yl]-N,N-dimethylacetamide Chemical compound FC(C1=CC=C(S1)C=1C=C2C(=NC=1)N(C(N2CC(=O)N(C)C)=O)C)F VMNLQDPQMDGDRZ-UHFFFAOYSA-N 0.000 claims 1
• KNCORNNLLGPEEH-UHFFFAOYSA-N 2-[6-[5-(difluoromethyl)thiophen-3-yl]-3-methyl-2-oxoimidazo[4,5-b]pyridin-1-yl]-N,N-dimethylacetamide Chemical compound FC(C1=CC(=CS1)C=1C=C2C(=NC=1)N(C(N2CC(=O)N(C)C)=O)C)F KNCORNNLLGPEEH-UHFFFAOYSA-N 0.000 claims 1
• KQSXVKNWZCGIKT-UHFFFAOYSA-N 2-[6-[5-(hydroxymethyl)thiophen-2-yl]-3-methyl-2-oxoimidazo[4,5-b]pyridin-1-yl]-N,N-dimethylacetamide Chemical compound OCC1=CC=C(S1)C=1C=C2C(=NC=1)N(C(N2CC(=O)N(C)C)=O)C KQSXVKNWZCGIKT-UHFFFAOYSA-N 0.000 claims 1
• ALQFHZDOTZLSOO-UHFFFAOYSA-N 2-[[2-oxo-6-[3-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridin-1-yl]methyl]benzonitrile Chemical compound O=C1N(C=2C(=NC=C(C=2)C2=CC(=CC=C2)C(F)(F)F)N1)CC1=C(C#N)C=CC=C1 ALQFHZDOTZLSOO-UHFFFAOYSA-N 0.000 claims 1
• LNRAWOZYKRYDMC-UHFFFAOYSA-N 2-[[6-(2,4-dimethoxyphenyl)-2-oxo-3H-imidazo[4,5-b]pyridin-1-yl]methyl]benzonitrile Chemical compound COC1=C(C=CC(=C1)OC)C=1C=C2C(=NC=1)NC(N2CC1=C(C#N)C=CC=C1)=O LNRAWOZYKRYDMC-UHFFFAOYSA-N 0.000 claims 1
• PDPFBSOCXFFPIH-UHFFFAOYSA-N 2-[[6-(2-ethoxy-5-fluorophenyl)-2-oxo-3H-imidazo[4,5-b]pyridin-1-yl]methyl]benzonitrile Chemical compound C(C)OC1=C(C=C(C=C1)F)C=1C=C2C(=NC=1)NC(N2CC1=C(C#N)C=CC=C1)=O PDPFBSOCXFFPIH-UHFFFAOYSA-N 0.000 claims 1
• RNOHYJYLGJWWCI-UHFFFAOYSA-N 2-[[6-(2-ethoxyphenyl)-2-oxo-3H-imidazo[4,5-b]pyridin-1-yl]methyl]benzonitrile Chemical compound C(C)OC1=C(C=CC=C1)C=1C=C2C(=NC=1)NC(N2CC1=C(C#N)C=CC=C1)=O RNOHYJYLGJWWCI-UHFFFAOYSA-N 0.000 claims 1
• MENVVUHKNRFZIF-UHFFFAOYSA-N 2-[[6-(2-fluoro-6-methoxyphenyl)-2-oxo-3H-imidazo[4,5-b]pyridin-1-yl]methyl]benzonitrile Chemical compound FC1=C(C(=CC=C1)OC)C=1C=C2C(=NC=1)NC(N2CC1=C(C#N)C=CC=C1)=O MENVVUHKNRFZIF-UHFFFAOYSA-N 0.000 claims 1
• MPKWYFMHRRSHMJ-UHFFFAOYSA-N 2-[[6-(3,5-dimethylphenyl)-2-oxo-3H-imidazo[4,5-b]pyridin-1-yl]methyl]benzonitrile Chemical compound CC=1C=C(C=C(C=1)C)C=1C=C2C(=NC=1)NC(N2CC1=C(C#N)C=CC=C1)=O MPKWYFMHRRSHMJ-UHFFFAOYSA-N 0.000 claims 1
• KZNXRUKEUCHRSW-UHFFFAOYSA-N 2-[[6-(3-cyanophenyl)-2-oxo-3H-imidazo[4,5-b]pyridin-1-yl]methyl]benzonitrile Chemical compound C(#N)C=1C=C(C=CC=1)C=1C=C2C(=NC=1)NC(N2CC1=C(C#N)C=CC=C1)=O KZNXRUKEUCHRSW-UHFFFAOYSA-N 0.000 claims 1
• DCZLZJMJJXTELH-UHFFFAOYSA-N 2-[[6-(3-fluoro-4-methoxyphenyl)-2-oxo-3H-imidazo[4,5-b]pyridin-1-yl]methyl]benzonitrile Chemical compound FC=1C=C(C=CC=1OC)C=1C=C2C(=NC=1)NC(N2CC1=C(C#N)C=CC=C1)=O DCZLZJMJJXTELH-UHFFFAOYSA-N 0.000 claims 1
• ZBDDVAPOFCENEY-UHFFFAOYSA-N 2-[[6-(3-methoxyphenyl)-2-oxo-3H-imidazo[4,5-b]pyridin-1-yl]methyl]benzonitrile Chemical compound COC=1C=C(C=CC=1)C=1C=C2C(=NC=1)NC(N2CC1=C(C#N)C=CC=C1)=O ZBDDVAPOFCENEY-UHFFFAOYSA-N 0.000 claims 1
• PFZZAKILOABJJK-UHFFFAOYSA-N 2-[[6-(4-chlorophenyl)-2-oxo-3H-imidazo[4,5-b]pyridin-1-yl]methyl]benzonitrile Chemical compound ClC1=CC=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC1=C(C#N)C=CC=C1)=O PFZZAKILOABJJK-UHFFFAOYSA-N 0.000 claims 1
• GGWXRTRDZCUNFL-UHFFFAOYSA-N 2-[[6-(4-fluoro-2-methoxyphenyl)-2-oxo-3H-imidazo[4,5-b]pyridin-1-yl]methyl]benzonitrile Chemical compound FC1=CC(=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC1=C(C#N)C=CC=C1)=O)OC GGWXRTRDZCUNFL-UHFFFAOYSA-N 0.000 claims 1
• GLVIRGMOZWJMEL-UHFFFAOYSA-N 2-[[6-(4-fluoro-2-methylphenyl)-2-oxo-3H-imidazo[4,5-b]pyridin-1-yl]methyl]benzonitrile Chemical compound FC1=CC(=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC1=C(C#N)C=CC=C1)=O)C GLVIRGMOZWJMEL-UHFFFAOYSA-N 0.000 claims 1
• PLYGFAMCHOZBHA-UHFFFAOYSA-N 2-[[6-(4-methoxy-3-methylphenyl)-2-oxo-3H-imidazo[4,5-b]pyridin-1-yl]methyl]benzonitrile Chemical compound COC1=C(C=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC1=C(C#N)C=CC=C1)=O)C PLYGFAMCHOZBHA-UHFFFAOYSA-N 0.000 claims 1
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• BWRBBWDKLYUBJM-UHFFFAOYSA-N 3-methyl-1-[(5-methyl-1,2-oxazol-3-yl)methyl]-6-[3-(trifluoromethyl)phenyl]imidazo[4,5-b]pyridin-2-one Chemical compound CN1C(N(C=2C1=NC=C(C=2)C1=CC(=CC=C1)C(F)(F)F)CC1=NOC(=C1)C)=O BWRBBWDKLYUBJM-UHFFFAOYSA-N 0.000 claims 1
• NOLLGPSKRNALCZ-UHFFFAOYSA-N 3-methyl-1-[(5-methyl-1,2-oxazol-3-yl)methyl]-6-[5-(trifluoromethyl)thiophen-2-yl]imidazo[4,5-b]pyridin-2-one Chemical compound CN1C(N(C=2C1=NC=C(C=2)C=1SC(=CC=1)C(F)(F)F)CC1=NOC(=C1)C)=O NOLLGPSKRNALCZ-UHFFFAOYSA-N 0.000 claims 1
• GLKFKNUELBYIAG-UHFFFAOYSA-N 3-methyl-1-[(5-methyl-1,3,4-oxadiazol-2-yl)methyl]-6-(5-methylthiophen-2-yl)imidazo[4,5-b]pyridin-2-one Chemical compound CN1C(N(C=2C1=NC=C(C=2)C=1SC(=CC=1)C)CC=1OC(=NN=1)C)=O GLKFKNUELBYIAG-UHFFFAOYSA-N 0.000 claims 1
• ZHMGDJXYALMVLK-UHFFFAOYSA-N 3-methyl-1-[(5-methyl-1,3,4-oxadiazol-2-yl)methyl]-6-[5-(trifluoromethyl)thiophen-2-yl]imidazo[4,5-b]pyridin-2-one Chemical compound CN1C(N(C=2C1=NC=C(C=2)C=1SC(=CC=1)C(F)(F)F)CC=1OC(=NN=1)C)=O ZHMGDJXYALMVLK-UHFFFAOYSA-N 0.000 claims 1
• JUYFHSJCSCDZBU-UHFFFAOYSA-N 3-methyl-6-(3-methylphenyl)-1-(pyridazin-3-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound CN1C(N(C=2C1=NC=C(C=2)C=1C=C(C=CC=1)C)CC=1N=NC=CC=1)=O JUYFHSJCSCDZBU-UHFFFAOYSA-N 0.000 claims 1
• FQOURQGFRRYVIQ-UHFFFAOYSA-N 3-methyl-6-(3-methylphenyl)-1-(pyridin-3-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound CN1C(N(C=2C1=NC=C(C=2)C=1C=C(C=CC=1)C)CC=1C=NC=CC=1)=O FQOURQGFRRYVIQ-UHFFFAOYSA-N 0.000 claims 1
• GZRRGDYNZLPZOQ-UHFFFAOYSA-N 3-methyl-6-(5-methylthiophen-2-yl)-1-(thiadiazol-4-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound CN1C(N(C=2C1=NC=C(C=2)C=1SC(=CC=1)C)CC=1N=NSC=1)=O GZRRGDYNZLPZOQ-UHFFFAOYSA-N 0.000 claims 1
• ODJPLILCQIMPDT-UHFFFAOYSA-N 3-methyl-6-(5-methylthiophen-2-yl)-1-[(1-methyltriazol-4-yl)methyl]imidazo[4,5-b]pyridin-2-one Chemical compound CN1C(N(C=2C1=NC=C(C=2)C=1SC(=CC=1)C)CC=1N=NN(C=1)C)=O ODJPLILCQIMPDT-UHFFFAOYSA-N 0.000 claims 1
• KYGSKHLIMOTDCB-UHFFFAOYSA-N 4-[[6-(4-methoxyphenyl)-2-oxo-3H-imidazo[4,5-b]pyridin-1-yl]methyl]benzonitrile Chemical compound COC1=CC=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC1=CC=C(C#N)C=C1)=O KYGSKHLIMOTDCB-UHFFFAOYSA-N 0.000 claims 1
• PNGSTIFEUIMHNL-UHFFFAOYSA-N 6-(2,3-difluorophenyl)-1-[(3-methylpyridin-2-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=CC=C1F)C=1C=C2C(=NC=1)NC(N2CC1=NC=CC=C1C)=O PNGSTIFEUIMHNL-UHFFFAOYSA-N 0.000 claims 1
• GXPOLIMJASHJOY-UHFFFAOYSA-N 6-(2,3-difluorophenyl)-1-[(5-fluoropyridin-3-yl)methyl]-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=CC=C1F)C=1C=C2C(=NC=1)N(C(N2CC=1C=NC=C(C=1)F)=O)C GXPOLIMJASHJOY-UHFFFAOYSA-N 0.000 claims 1
• BZHNUBPUQWUDLK-UHFFFAOYSA-N 6-(2,3-difluorophenyl)-1-[(5-fluoropyridin-3-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=CC=C1F)C=1C=C2C(=NC=1)NC(N2CC=1C=NC=C(C=1)F)=O BZHNUBPUQWUDLK-UHFFFAOYSA-N 0.000 claims 1
• LGFSSMDCFHCTDR-UHFFFAOYSA-N 6-(2,3-difluorophenyl)-1-[(5-methylpyridin-3-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=CC=C1F)C=1C=C2C(=NC=1)NC(N2CC=1C=NC=C(C=1)C)=O LGFSSMDCFHCTDR-UHFFFAOYSA-N 0.000 claims 1
• HPFRVPJUVRRCBF-UHFFFAOYSA-N 6-(2,3-dimethoxyphenyl)-1-[(4-fluorophenyl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound COC1=C(C=CC=C1OC)C=1C=C2C(=NC=1)NC(N2CC1=CC=C(C=C1)F)=O HPFRVPJUVRRCBF-UHFFFAOYSA-N 0.000 claims 1
• QZXVBCNIPAYNTI-UHFFFAOYSA-N 6-(2,3-dimethylphenyl)-1-[2-(3-fluoroazetidin-1-yl)ethyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CC1=C(C=CC=C1C)C=1C=C2C(=NC=1)NC(N2CCN1CC(C1)F)=O QZXVBCNIPAYNTI-UHFFFAOYSA-N 0.000 claims 1
• GPZGIZRHGMSOFF-UHFFFAOYSA-N 6-(2,4-difluoro-3-methylphenyl)-1-(2-hydroxybutyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CCC(O)Cn1c2cc(cnc2[nH]c1=O)-c1ccc(F)c(C)c1F GPZGIZRHGMSOFF-UHFFFAOYSA-N 0.000 claims 1
• JBGDMRZEUCZMPN-UHFFFAOYSA-N 6-(2,4-difluoro-3-methylphenyl)-1-(2-oxobutyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=CC(=C1C)F)C=1C=C2C(=NC=1)NC(N2CC(CC)=O)=O JBGDMRZEUCZMPN-UHFFFAOYSA-N 0.000 claims 1
• LNFQDCARIOXIDP-UHFFFAOYSA-N 6-(2,4-difluoro-3-methylphenyl)-1-(pyridin-2-ylmethyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=CC(=C1C)F)C=1C=C2C(=NC=1)NC(N2CC1=NC=CC=C1)=O LNFQDCARIOXIDP-UHFFFAOYSA-N 0.000 claims 1
• JHWJWHNLZXKLSB-UHFFFAOYSA-N 6-(2,4-difluoro-3-methylphenyl)-1-(pyridin-3-ylmethyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=CC(=C1C)F)C=1C=C2C(=NC=1)NC(N2CC=1C=NC=CC=1)=O JHWJWHNLZXKLSB-UHFFFAOYSA-N 0.000 claims 1
• IAASGYMRJNKPON-UHFFFAOYSA-N 6-(2,4-difluoro-3-methylphenyl)-1-[(3-methylpyridin-2-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=CC(=C1C)F)C=1C=C2C(=NC=1)NC(N2CC1=NC=CC=C1C)=O IAASGYMRJNKPON-UHFFFAOYSA-N 0.000 claims 1
• OWTWPIMULQSRTK-UHFFFAOYSA-N 6-(2,4-difluoro-3-methylphenyl)-1-[(4-methylpyridin-3-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=CC(=C1C)F)C=1C=C2C(=NC=1)NC(N2CC=1C=NC=CC=1C)=O OWTWPIMULQSRTK-UHFFFAOYSA-N 0.000 claims 1
• CFQADSXRCMFKCM-UHFFFAOYSA-N 6-(2,4-difluoro-3-methylphenyl)-1-[(5-fluoropyridin-3-yl)methyl]-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=CC(=C1C)F)C=1C=C2C(=NC=1)N(C(N2CC=1C=NC=C(C=1)F)=O)C CFQADSXRCMFKCM-UHFFFAOYSA-N 0.000 claims 1
• XIAJDKMAUXWGQW-UHFFFAOYSA-N 6-(2,4-difluoro-3-methylphenyl)-1-[(5-fluoropyridin-3-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=CC(=C1C)F)C=1C=C2C(=NC=1)NC(N2CC=1C=NC=C(C=1)F)=O XIAJDKMAUXWGQW-UHFFFAOYSA-N 0.000 claims 1
• FTQXXOICAMTGLR-UHFFFAOYSA-N 6-(2,4-difluoro-3-methylphenyl)-1-[(5-methylpyridin-3-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=CC(=C1C)F)C=1C=C2C(=NC=1)NC(N2CC=1C=NC=C(C=1)C)=O FTQXXOICAMTGLR-UHFFFAOYSA-N 0.000 claims 1
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• SKNGTYNLYDWART-UHFFFAOYSA-N 6-(3,5-difluorophenyl)-1-[(5-methylpyridin-3-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC=1C=C(C=C(C=1)F)C=1C=C2C(=NC=1)NC(N2CC=1C=NC=C(C=1)C)=O SKNGTYNLYDWART-UHFFFAOYSA-N 0.000 claims 1
• YIEYNPGTBZZBNU-UHFFFAOYSA-N 6-(3,5-difluorophenyl)-1-[2-(2-hydroxyethylamino)ethyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC=1C=C(C=C(C=1)F)C=1C=C2C(=NC=1)NC(N2CCNCCO)=O YIEYNPGTBZZBNU-UHFFFAOYSA-N 0.000 claims 1
• MPJBYVWJAILZAA-UHFFFAOYSA-N 6-(3,5-difluorophenyl)-1-[2-(3-hydroxypyrrolidin-1-yl)ethyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC=1C=C(C=C(C=1)F)C=1C=C2C(=NC=1)NC(N2CCN1CC(CC1)O)=O MPJBYVWJAILZAA-UHFFFAOYSA-N 0.000 claims 1
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• YSYDPBQMKKIPOR-UHFFFAOYSA-N 6-(3,5-difluorophenyl)-3-methyl-1-(pyridin-3-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound FC=1C=C(C=C(C=1)F)C=1C=C2C(=NC=1)N(C(N2CC=1C=NC=CC=1)=O)C YSYDPBQMKKIPOR-UHFFFAOYSA-N 0.000 claims 1
• MOVZEVIJFFNUQE-UHFFFAOYSA-N 6-(3,5-dimethylphenyl)-1-[(3-fluorophenyl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CC=1C=C(C=C(C=1)C)C=1C=C2C(=NC=1)NC(N2CC1=CC(=CC=C1)F)=O MOVZEVIJFFNUQE-UHFFFAOYSA-N 0.000 claims 1
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• LFJBENGPFDNWFR-UHFFFAOYSA-N 6-(3-chloro-2-fluorophenyl)-1-[(5-fluoropyridin-3-yl)methyl]-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound ClC=1C(=C(C=CC=1)C=1C=C2C(=NC=1)N(C(N2CC=1C=NC=C(C=1)F)=O)C)F LFJBENGPFDNWFR-UHFFFAOYSA-N 0.000 claims 1
• QRCZCDBCDCHNTN-UHFFFAOYSA-N 6-(3-chloro-2-fluorophenyl)-3-methyl-1-(pyridin-3-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound ClC=1C(=C(C=CC=1)C=1C=C2C(=NC=1)N(C(N2CC=1C=NC=CC=1)=O)C)F QRCZCDBCDCHNTN-UHFFFAOYSA-N 0.000 claims 1
• AIGPRXBLOOQCFJ-UHFFFAOYSA-N 6-(3-chloro-4-fluorophenyl)-1-(2-oxo-2-thiophen-2-ylethyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound ClC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)NC(N2CC(C=1SC=CC=1)=O)=O AIGPRXBLOOQCFJ-UHFFFAOYSA-N 0.000 claims 1
• YZXMPWCEWOTHIB-UHFFFAOYSA-N 6-(3-chloro-4-fluorophenyl)-1-[(1-methylpyrazol-3-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound ClC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)NC(N2CC1=NN(C=C1)C)=O YZXMPWCEWOTHIB-UHFFFAOYSA-N 0.000 claims 1
• ZIPHJYHYXLAHKY-UHFFFAOYSA-N 6-(3-chloro-4-fluorophenyl)-1-[(4-fluorophenyl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound ClC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)NC(N2CC1=CC=C(C=C1)F)=O ZIPHJYHYXLAHKY-UHFFFAOYSA-N 0.000 claims 1
• FMIAMQMNCXUHOE-UHFFFAOYSA-N 6-(3-chloro-4-fluorophenyl)-3-methyl-1-(pyridazin-3-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound ClC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)N(C(N2CC=1N=NC=CC=1)=O)C FMIAMQMNCXUHOE-UHFFFAOYSA-N 0.000 claims 1
• LPPIEHTWOZOECK-UHFFFAOYSA-N 6-(3-chloro-4-fluorophenyl)-3-methyl-1-(pyridin-3-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound ClC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)N(C(N2CC=1C=NC=CC=1)=O)C LPPIEHTWOZOECK-UHFFFAOYSA-N 0.000 claims 1
• MJFPVKHRGGNHAW-UHFFFAOYSA-N 6-(3-chlorophenyl)-1-(pyridin-2-ylmethyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound ClC=1C=C(C=CC=1)C=1C=C2C(=NC=1)NC(N2CC1=NC=CC=C1)=O MJFPVKHRGGNHAW-UHFFFAOYSA-N 0.000 claims 1
• PCDJNCAZXCSRDY-UHFFFAOYSA-N 6-(3-chlorophenyl)-1-(pyridin-3-ylmethyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound ClC=1C=C(C=CC=1)C=1C=C2C(=NC=1)NC(N2CC=1C=NC=CC=1)=O PCDJNCAZXCSRDY-UHFFFAOYSA-N 0.000 claims 1
• MFZSKMBOJAJAOX-UHFFFAOYSA-N 6-(3-chlorophenyl)-1-[(5-fluoropyridin-3-yl)methyl]-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound ClC=1C=C(C=CC=1)C=1C=C2C(=NC=1)N(C(N2CC=1C=NC=C(C=1)F)=O)C MFZSKMBOJAJAOX-UHFFFAOYSA-N 0.000 claims 1
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• UNRWTKWGXZAANO-UHFFFAOYSA-N 6-(3-chlorophenyl)-3-methyl-1-(pyridazin-3-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound ClC=1C=C(C=CC=1)C=1C=C2C(=NC=1)N(C(N2CC=1N=NC=CC=1)=O)C UNRWTKWGXZAANO-UHFFFAOYSA-N 0.000 claims 1
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• PHWFXSUUZJACQL-UHFFFAOYSA-N 6-(3-ethoxyphenyl)-1-(2-oxo-2-thiophen-2-ylethyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound C(C)OC=1C=C(C=CC=1)C=1C=C2C(=NC=1)NC(N2CC(C=1SC=CC=1)=O)=O PHWFXSUUZJACQL-UHFFFAOYSA-N 0.000 claims 1
• QXRHHXIUQHPDEK-UHFFFAOYSA-N 6-(3-fluoro-4-methoxyphenyl)-1-(2-oxo-2-thiophen-2-ylethyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC=1C=C(C=CC=1OC)C=1C=C2C(=NC=1)NC(N2CC(C=1SC=CC=1)=O)=O QXRHHXIUQHPDEK-UHFFFAOYSA-N 0.000 claims 1
• FJSJWLSFOAQCQW-UHFFFAOYSA-N 6-(3-fluoro-4-methoxyphenyl)-1-[(5-methyl-1,2-oxazol-3-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC=1C=C(C=CC=1OC)C=1C=C2C(=NC=1)NC(N2CC1=NOC(=C1)C)=O FJSJWLSFOAQCQW-UHFFFAOYSA-N 0.000 claims 1
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• SWLJWWSRYQXGBS-UHFFFAOYSA-N 6-(3-fluorophenyl)-1-(pyridin-2-ylmethyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC=1C=C(C=CC=1)C=1C=C2C(=NC=1)NC(N2CC1=NC=CC=C1)=O SWLJWWSRYQXGBS-UHFFFAOYSA-N 0.000 claims 1
• KWCVQGUTBQQXIA-UHFFFAOYSA-N 6-(3-fluorophenyl)-1-(pyridin-3-ylmethyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC=1C=C(C=CC=1)C=1C=C2C(=NC=1)NC(N2CC=1C=NC=CC=1)=O KWCVQGUTBQQXIA-UHFFFAOYSA-N 0.000 claims 1
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• POKYDAYYHJBBKN-UHFFFAOYSA-N 6-(3-fluorophenyl)-1-[(4-methylpyridin-3-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC=1C=C(C=CC=1)C=1C=C2C(=NC=1)NC(N2CC=1C=NC=CC=1C)=O POKYDAYYHJBBKN-UHFFFAOYSA-N 0.000 claims 1
• MZRAHPCZYOEOFR-UHFFFAOYSA-N 6-(3-fluorophenyl)-1-[(5-methylpyridin-3-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC=1C=C(C=CC=1)C=1C=C2C(=NC=1)NC(N2CC=1C=NC=C(C=1)C)=O MZRAHPCZYOEOFR-UHFFFAOYSA-N 0.000 claims 1
• YVKXTPFSPWQWMN-UHFFFAOYSA-N 6-(3-fluorophenyl)-3-methyl-1-(pyridin-2-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound FC=1C=C(C=CC=1)C=1C=C2C(=NC=1)N(C(N2CC1=NC=CC=C1)=O)C YVKXTPFSPWQWMN-UHFFFAOYSA-N 0.000 claims 1
• IVBXHPCMJSPNIW-UHFFFAOYSA-N 6-(3-fluorophenyl)-3-methyl-1-(pyridin-4-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound FC=1C=C(C=CC=1)C=1C=C2C(=NC=1)N(C(N2CC1=CC=NC=C1)=O)C IVBXHPCMJSPNIW-UHFFFAOYSA-N 0.000 claims 1
• TXLSDYJCGLULQY-UHFFFAOYSA-N 6-(3-fluorophenyl)-3-methyl-1-(pyrimidin-2-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound FC=1C=C(C=CC=1)C=1C=C2C(=NC=1)N(C(N2CC1=NC=CC=N1)=O)C TXLSDYJCGLULQY-UHFFFAOYSA-N 0.000 claims 1
• KBMPSPPLRJMZLJ-UHFFFAOYSA-N 6-(3-fluorophenyl)-3-methyl-1-(pyrimidin-4-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound FC=1C=C(C=CC=1)C=1C=C2C(=NC=1)N(C(N2CC1=NC=NC=C1)=O)C KBMPSPPLRJMZLJ-UHFFFAOYSA-N 0.000 claims 1
• BQWRIEKRJUDRNQ-UHFFFAOYSA-N 6-(3-fluorophenyl)-3-methyl-1-(pyrimidin-5-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound FC=1C=C(C=CC=1)C=1C=C2C(=NC=1)N(C(N2CC=1C=NC=NC=1)=O)C BQWRIEKRJUDRNQ-UHFFFAOYSA-N 0.000 claims 1
• GSEZDLMDCKKJAC-UHFFFAOYSA-N 6-(3-methoxyphenyl)-1-(2-oxo-2-thiophen-2-ylethyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound COC=1C=C(C=CC=1)C=1C=C2C(=NC=1)NC(N2CC(C=1SC=CC=1)=O)=O GSEZDLMDCKKJAC-UHFFFAOYSA-N 0.000 claims 1
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• SHSFMAJCTVNWCJ-UHFFFAOYSA-N 6-(3-methylphenyl)-1-(2-oxobutyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound C1(=CC(=CC=C1)C=1C=C2C(=NC=1)NC(N2CC(CC)=O)=O)C SHSFMAJCTVNWCJ-UHFFFAOYSA-N 0.000 claims 1
• INOVNSMGJZPYFW-UHFFFAOYSA-N 6-(3-methylphenyl)-1-(pyridin-3-ylmethyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound C1(=CC(=CC=C1)C=1C=C2C(=NC=1)NC(N2CC=1C=NC=CC=1)=O)C INOVNSMGJZPYFW-UHFFFAOYSA-N 0.000 claims 1
• ZWPLTMJMBILTQY-UHFFFAOYSA-N 6-(4-chloro-3-methylphenyl)-1-[(5-fluoropyridin-3-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound ClC1=C(C=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC=1C=NC=C(C=1)F)=O)C ZWPLTMJMBILTQY-UHFFFAOYSA-N 0.000 claims 1
• OSDWGJXSGNZQNA-UHFFFAOYSA-N 6-(4-chlorophenyl)-1-(2-oxo-2-thiophen-2-ylethyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound ClC1=CC=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC(C=1SC=CC=1)=O)=O OSDWGJXSGNZQNA-UHFFFAOYSA-N 0.000 claims 1
• UFDBAZRKELJQIF-UHFFFAOYSA-N 6-(4-chlorophenyl)-1-[(4-propan-2-ylphenyl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound ClC1=CC=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC1=CC=C(C=C1)C(C)C)=O UFDBAZRKELJQIF-UHFFFAOYSA-N 0.000 claims 1
• QJYKOFHHQQZJII-UHFFFAOYSA-N 6-(4-fluoro-2-methoxyphenyl)-1-(2-oxo-2-thiophen-2-ylethyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=CC(=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC(C=1SC=CC=1)=O)=O)OC QJYKOFHHQQZJII-UHFFFAOYSA-N 0.000 claims 1
• RCKYTLDLQSDFHL-UHFFFAOYSA-N 6-(4-fluoro-2-methoxyphenyl)-1-[(3-fluorophenyl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=CC(=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC1=CC(=CC=C1)F)=O)OC RCKYTLDLQSDFHL-UHFFFAOYSA-N 0.000 claims 1
• DDYSFQDYBZYNDQ-UHFFFAOYSA-N 6-(4-fluoro-2-methoxyphenyl)-1-[(3-methoxyphenyl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=CC(=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC1=CC(=CC=C1)OC)=O)OC DDYSFQDYBZYNDQ-UHFFFAOYSA-N 0.000 claims 1
• HFXRBYHYHTVUSY-UHFFFAOYSA-N 6-(4-fluoro-2-methoxyphenyl)-1-[(4-fluorophenyl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=CC(=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC1=CC=C(C=C1)F)=O)OC HFXRBYHYHTVUSY-UHFFFAOYSA-N 0.000 claims 1
• NEPWJFBYPNTGKZ-UHFFFAOYSA-N 6-(4-fluoro-2-methoxyphenyl)-1-[(5-methyl-1,2-oxazol-3-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=CC(=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC1=NOC(=C1)C)=O)OC NEPWJFBYPNTGKZ-UHFFFAOYSA-N 0.000 claims 1
• CWOHTOWXXYVVBG-UHFFFAOYSA-N 6-(4-fluoro-2-methylphenyl)-1-(2-methoxyethyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=CC(=C(C=C1)C=1C=C2C(=NC=1)NC(N2CCOC)=O)C CWOHTOWXXYVVBG-UHFFFAOYSA-N 0.000 claims 1
• OKEHZFISYXHQKN-UHFFFAOYSA-N 6-(4-fluoro-2-methylphenyl)-1-(2-pyrrolidin-1-ylethyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=CC(=C(C=C1)C=1C=C2C(=NC=1)NC(N2CCN1CCCC1)=O)C OKEHZFISYXHQKN-UHFFFAOYSA-N 0.000 claims 1
• TUOSBGNVQORYHN-UHFFFAOYSA-N 6-(4-fluoro-2-methylphenyl)-1-[(4-fluorophenyl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=CC(=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC1=CC=C(C=C1)F)=O)C TUOSBGNVQORYHN-UHFFFAOYSA-N 0.000 claims 1
• TZDKKGHDYQLYKY-UHFFFAOYSA-N 6-(4-fluoro-2-methylphenyl)-1-[(5-methyl-1,2-oxazol-3-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=CC(=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC1=NOC(=C1)C)=O)C TZDKKGHDYQLYKY-UHFFFAOYSA-N 0.000 claims 1
• QRCZYAIDMYYMME-UHFFFAOYSA-N 6-(4-fluoro-2-methylphenyl)-3-methyl-1-(oxetan-2-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound CN1C(=O)N(CC2CCO2)C2=C1N=CC(=C2)C1=CC=C(F)C=C1C QRCZYAIDMYYMME-UHFFFAOYSA-N 0.000 claims 1
• DEHZJGNEFCRBIT-UHFFFAOYSA-N 6-(4-fluoro-3-methylphenyl)-1-(2-oxobutyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC(CC)=O)=O)C DEHZJGNEFCRBIT-UHFFFAOYSA-N 0.000 claims 1
• VHOJRYIGQTUSBG-UHFFFAOYSA-N 6-(4-fluoro-3-methylphenyl)-1-(pyridin-2-ylmethyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC1=NC=CC=C1)=O)C VHOJRYIGQTUSBG-UHFFFAOYSA-N 0.000 claims 1
• KKCRGJQSXQBZEZ-UHFFFAOYSA-N 6-(4-fluoro-3-methylphenyl)-1-(pyridin-3-ylmethyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC=1C=NC=CC=1)=O)C KKCRGJQSXQBZEZ-UHFFFAOYSA-N 0.000 claims 1
• SLXHPBCGDHBTEW-UHFFFAOYSA-N 6-(4-fluoro-3-methylphenyl)-1-[(1-methylpyrazol-3-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC1=NN(C=C1)C)=O)C SLXHPBCGDHBTEW-UHFFFAOYSA-N 0.000 claims 1
• AUBLIISEHJJQIB-UHFFFAOYSA-N 6-(4-fluoro-3-methylphenyl)-1-[(3-methylpyridin-2-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC1=NC=CC=C1C)=O)C AUBLIISEHJJQIB-UHFFFAOYSA-N 0.000 claims 1
• LWKSTLXAFOKHNM-UHFFFAOYSA-N 6-(4-fluoro-3-methylphenyl)-1-[(4-methylpyridin-3-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC=1C=NC=CC=1C)=O)C LWKSTLXAFOKHNM-UHFFFAOYSA-N 0.000 claims 1
• PSLNXKHAFLYZTM-UHFFFAOYSA-N 6-(4-fluoro-3-methylphenyl)-1-[(5-fluoropyridin-3-yl)methyl]-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)N(C(N2CC=1C=NC=C(C=1)F)=O)C)C PSLNXKHAFLYZTM-UHFFFAOYSA-N 0.000 claims 1
• LVOLXARNQNCSGZ-UHFFFAOYSA-N 6-(4-fluoro-3-methylphenyl)-1-[(5-fluoropyridin-3-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC=1C=NC=C(C=1)F)=O)C LVOLXARNQNCSGZ-UHFFFAOYSA-N 0.000 claims 1
• ULYILMIYKRTPRT-UHFFFAOYSA-N 6-(4-fluoro-3-methylphenyl)-3-methyl-1-(2-oxobutyl)imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)N(C(N2CC(CC)=O)=O)C)C ULYILMIYKRTPRT-UHFFFAOYSA-N 0.000 claims 1
• RBEPWGMQWTVBBH-UHFFFAOYSA-N 6-(4-fluoro-3-methylphenyl)-3-methyl-1-(pyrazin-2-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)N(C(N2CC1=NC=CN=C1)=O)C)C RBEPWGMQWTVBBH-UHFFFAOYSA-N 0.000 claims 1
• UVIUKXUJQHUUNV-UHFFFAOYSA-N 6-(4-fluoro-3-methylphenyl)-3-methyl-1-(pyridazin-3-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)N(C(N2CC=1N=NC=CC=1)=O)C)C UVIUKXUJQHUUNV-UHFFFAOYSA-N 0.000 claims 1
• FMTJUVZKHPARMP-UHFFFAOYSA-N 6-(4-fluoro-3-methylphenyl)-3-methyl-1-(pyridin-2-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)N(C(N2CC1=NC=CC=C1)=O)C)C FMTJUVZKHPARMP-UHFFFAOYSA-N 0.000 claims 1
• RJNJTWPHYNXNOR-UHFFFAOYSA-N 6-(4-fluoro-3-methylphenyl)-3-methyl-1-(pyridin-4-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)N(C(N2CC1=CC=NC=C1)=O)C)C RJNJTWPHYNXNOR-UHFFFAOYSA-N 0.000 claims 1
• REZBHKMZDPPUOQ-UHFFFAOYSA-N 6-(4-fluoro-3-methylphenyl)-3-methyl-1-(pyrimidin-2-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)N(C(N2CC1=NC=CC=N1)=O)C)C REZBHKMZDPPUOQ-UHFFFAOYSA-N 0.000 claims 1
• JHMLFYYZIDNVBJ-UHFFFAOYSA-N 6-(4-fluoro-3-methylphenyl)-3-methyl-1-(pyrimidin-4-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)N(C(N2CC1=NC=NC=C1)=O)C)C JHMLFYYZIDNVBJ-UHFFFAOYSA-N 0.000 claims 1
• DOYVBJZTANGNFR-UHFFFAOYSA-N 6-(4-fluoro-3-methylphenyl)-3-methyl-1-(pyrimidin-5-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)N(C(N2CC=1C=NC=NC=1)=O)C)C DOYVBJZTANGNFR-UHFFFAOYSA-N 0.000 claims 1
• NQZTYQQPEJLIJH-UHFFFAOYSA-N 6-(4-fluorophenyl)-1-(pyridin-2-ylmethyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC1=NC=CC=C1)=O NQZTYQQPEJLIJH-UHFFFAOYSA-N 0.000 claims 1
• WLIGFRSFZDICAK-UHFFFAOYSA-N 6-(4-fluorophenyl)-1-(pyridin-3-ylmethyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC=1C=NC=CC=1)=O WLIGFRSFZDICAK-UHFFFAOYSA-N 0.000 claims 1
• OOBDVXJKOFIZQR-UHFFFAOYSA-N 6-(4-fluorophenyl)-1-[(1-methyl-1,2,4-triazol-3-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC1=NN(C=N1)C)=O OOBDVXJKOFIZQR-UHFFFAOYSA-N 0.000 claims 1
• OYEAPRJEKUIDDR-UHFFFAOYSA-N 6-(4-fluorophenyl)-1-[(1-methylpyrazol-3-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC1=NN(C=C1)C)=O OYEAPRJEKUIDDR-UHFFFAOYSA-N 0.000 claims 1
• GGPPTOCKYIFYFI-UHFFFAOYSA-N 6-(4-fluorophenyl)-1-[(1-methylpyrazol-4-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC=1C=NN(C=1)C)=O GGPPTOCKYIFYFI-UHFFFAOYSA-N 0.000 claims 1
• VPHZCAMZHXTFPV-UHFFFAOYSA-N 6-(4-fluorophenyl)-1-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC1=NC(=NO1)C)=O VPHZCAMZHXTFPV-UHFFFAOYSA-N 0.000 claims 1
• XBOYMQBHPFURQP-UHFFFAOYSA-N 6-(4-fluorophenyl)-1-[(5-methyl-1,2-oxazol-3-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC1=NOC(=C1)C)=O XBOYMQBHPFURQP-UHFFFAOYSA-N 0.000 claims 1
• DXTAAOZLLQGWIA-UHFFFAOYSA-N 6-(4-fluorophenyl)-1-[(5-methyl-1,3,4-oxadiazol-2-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC=1OC(=NN=1)C)=O DXTAAOZLLQGWIA-UHFFFAOYSA-N 0.000 claims 1
• RHMXWYOMEIIXLS-UHFFFAOYSA-N 6-(4-methoxy-3-methylphenyl)-1-[(5-methyl-1,2-oxazol-3-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound COC1=C(C=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC1=NOC(=C1)C)=O)C RHMXWYOMEIIXLS-UHFFFAOYSA-N 0.000 claims 1
• PIJDARDKFIDNKD-UHFFFAOYSA-N 6-(4-methoxyphenyl)-1-(2-morpholin-4-yl-2-oxoethyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound COC1=CC=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC(=O)N1CCOCC1)=O PIJDARDKFIDNKD-UHFFFAOYSA-N 0.000 claims 1
• IZOUESKKPYWYCM-UHFFFAOYSA-N 6-(4-methoxyphenyl)-1-(2-oxo-2-thiophen-2-ylethyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound COC1=CC=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC(C=1SC=CC=1)=O)=O IZOUESKKPYWYCM-UHFFFAOYSA-N 0.000 claims 1
• UZCOIGIHKDBMDQ-UHFFFAOYSA-N 6-(4-methylphenyl)-1-(pyridin-2-ylmethyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound C1(=CC=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC1=NC=CC=C1)=O)C UZCOIGIHKDBMDQ-UHFFFAOYSA-N 0.000 claims 1
• LIMSLWSHINXEKC-UHFFFAOYSA-N 6-(4-tert-butylphenyl)-1-[(3,4-dimethoxypyridin-2-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC1=NC=CC(=C1OC)OC)=O LIMSLWSHINXEKC-UHFFFAOYSA-N 0.000 claims 1
• HKHUYNLFJGXKRR-UHFFFAOYSA-N 6-(5-chloro-4-methylthiophen-2-yl)-1-[(5-chloropyridin-3-yl)methyl]-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound ClC1=C(C=C(S1)C=1C=C2C(=NC=1)N(C(N2CC=1C=NC=C(C=1)Cl)=O)C)C HKHUYNLFJGXKRR-UHFFFAOYSA-N 0.000 claims 1
• CXAZLNRLKAIXTF-UHFFFAOYSA-N 6-(5-chloro-4-methylthiophen-2-yl)-3-methyl-1-(pyridin-3-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound ClC1=C(C=C(S1)C=1C=C2C(=NC=1)N(C(N2CC=1C=NC=CC=1)=O)C)C CXAZLNRLKAIXTF-UHFFFAOYSA-N 0.000 claims 1
• KGHCBOGJKCPXLM-UHFFFAOYSA-N 6-(5-cyclopropylthiophen-2-yl)-1-[2-(3-fluoroazetidin-1-yl)-2-oxoethyl]-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound C1(CC1)C1=CC=C(S1)C=1C=C2C(=NC=1)N(C(N2CC(=O)N1CC(C1)F)=O)C KGHCBOGJKCPXLM-UHFFFAOYSA-N 0.000 claims 1
• GAEJXNPSCRSOQS-UHFFFAOYSA-N 6-(5-ethylthiophen-2-yl)-1-[2-(3-fluoroazetidin-1-yl)-2-oxoethyl]-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound C(C)C1=CC=C(S1)C=1C=C2C(=NC=1)N(C(N2CC(=O)N1CC(C1)F)=O)C GAEJXNPSCRSOQS-UHFFFAOYSA-N 0.000 claims 1
• BSGURCDMDBLAIA-UHFFFAOYSA-N 6-(5-fluorothiophen-2-yl)-3-methyl-1-(pyridazin-3-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound FC1=CC=C(S1)C=1C=C2C(=NC=1)N(C(N2CC=1N=NC=CC=1)=O)C BSGURCDMDBLAIA-UHFFFAOYSA-N 0.000 claims 1
• HPIHONOMNSDOPG-UHFFFAOYSA-N 6-(6-fluoropyridin-2-yl)-1-(2-oxobutyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=CC=CC(=N1)C=1C=C2C(=NC=1)NC(N2CC(CC)=O)=O HPIHONOMNSDOPG-UHFFFAOYSA-N 0.000 claims 1
• TXRVVAFJUFYXIG-UHFFFAOYSA-N 6-[3,4-difluoro-5-(trifluoromethyl)phenyl]-3-methyl-1-(pyridazin-3-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound FC=1C=C(C=C(C=1F)C(F)(F)F)C=1C=C2C(=NC=1)N(C(N2CC=1N=NC=CC=1)=O)C TXRVVAFJUFYXIG-UHFFFAOYSA-N 0.000 claims 1
• GWUGIJXROHNBGW-UHFFFAOYSA-N 6-[3-(difluoromethoxy)-4-fluorophenyl]-1-[(5-fluoropyridin-3-yl)methyl]-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound FC(OC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)N(C(N2CC=1C=NC=C(C=1)F)=O)C)F GWUGIJXROHNBGW-UHFFFAOYSA-N 0.000 claims 1
• SQDUXNSZELCFMR-UHFFFAOYSA-N 6-[3-(difluoromethoxy)-4-fluorophenyl]-3-methyl-1-(pyridazin-3-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound FC(OC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)N(C(N2CC=1N=NC=CC=1)=O)C)F SQDUXNSZELCFMR-UHFFFAOYSA-N 0.000 claims 1
• YSCWZYSSEFCNCE-UHFFFAOYSA-N 6-[3-(difluoromethoxy)phenyl]-1-(pyridin-3-ylmethyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC(OC=1C=C(C=CC=1)C=1C=C2C(=NC=1)NC(N2CC=1C=NC=CC=1)=O)F YSCWZYSSEFCNCE-UHFFFAOYSA-N 0.000 claims 1
• JJIUVVPYZSXRQI-UHFFFAOYSA-N 6-[3-(difluoromethoxy)phenyl]-1-[(5-fluoropyridin-3-yl)methyl]-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound FC(OC=1C=C(C=CC=1)C=1C=C2C(=NC=1)N(C(N2CC=1C=NC=C(C=1)F)=O)C)F JJIUVVPYZSXRQI-UHFFFAOYSA-N 0.000 claims 1
• JTXJASHBNMQNFZ-UHFFFAOYSA-N 6-[3-(difluoromethoxy)phenyl]-1-[(5-fluoropyridin-3-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC(OC=1C=C(C=CC=1)C=1C=C2C(=NC=1)NC(N2CC=1C=NC=C(C=1)F)=O)F JTXJASHBNMQNFZ-UHFFFAOYSA-N 0.000 claims 1
• CAQXELHWIMPARY-UHFFFAOYSA-N 6-[3-(difluoromethyl)-4-fluorophenyl]-1-[(5-fluoropyridin-3-yl)methyl]-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)N(C(N2CC=1C=NC=C(C=1)F)=O)C)F CAQXELHWIMPARY-UHFFFAOYSA-N 0.000 claims 1
• BMJMCYYKVKPQBO-UHFFFAOYSA-N 6-[3-(difluoromethyl)-4-fluorophenyl]-1-[2-(3-fluoroazetidin-1-yl)-2-oxoethyl]-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)N(C(N2CC(=O)N1CC(C1)F)=O)C)F BMJMCYYKVKPQBO-UHFFFAOYSA-N 0.000 claims 1
• XXVQFSMGGVMWLV-UHFFFAOYSA-N 6-[3-(difluoromethyl)-4-fluorophenyl]-3-methyl-1-(pyridazin-3-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)N(C(N2CC=1N=NC=CC=1)=O)C)F XXVQFSMGGVMWLV-UHFFFAOYSA-N 0.000 claims 1
• BLTUAIMDQSBZLW-UHFFFAOYSA-N 6-[3-(difluoromethyl)phenyl]-1-(pyridin-2-ylmethyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC(C=1C=C(C=CC=1)C=1C=C2C(=NC=1)NC(N2CC1=NC=CC=C1)=O)F BLTUAIMDQSBZLW-UHFFFAOYSA-N 0.000 claims 1
• ZQEZTCLUXNHMCA-UHFFFAOYSA-N 6-[3-(difluoromethyl)phenyl]-1-(pyridin-3-ylmethyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC(C=1C=C(C=CC=1)C=1C=C2C(=NC=1)NC(N2CC=1C=NC=CC=1)=O)F ZQEZTCLUXNHMCA-UHFFFAOYSA-N 0.000 claims 1
• PZWIDHYFDZPUMO-UHFFFAOYSA-N 6-[3-(difluoromethyl)phenyl]-1-[(5-fluoropyridin-3-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC(C=1C=C(C=CC=1)C=1C=C2C(=NC=1)NC(N2CC=1C=NC=C(C=1)F)=O)F PZWIDHYFDZPUMO-UHFFFAOYSA-N 0.000 claims 1
• YYFAXNDGFHTVEQ-UHFFFAOYSA-N 6-[3-(dimethylamino)phenyl]-1-[(3-fluorophenyl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CN(C=1C=C(C=CC=1)C=1C=C2C(=NC=1)NC(N2CC1=CC(=CC=C1)F)=O)C YYFAXNDGFHTVEQ-UHFFFAOYSA-N 0.000 claims 1
• DMVJBHJAHJIWCB-UHFFFAOYSA-N 6-[3-(trifluoromethyl)phenyl]-1-[[4-(trifluoromethyl)phenyl]methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC(C=1C=C(C=CC=1)C=1C=C2C(=NC=1)NC(N2CC1=CC=C(C=C1)C(F)(F)F)=O)(F)F DMVJBHJAHJIWCB-UHFFFAOYSA-N 0.000 claims 1
• RKKKAEBSWYCVKP-UHFFFAOYSA-N 6-[3-(trifluoromethyl)phenyl]-1-[[4-(trifluoromethyl)pyridin-3-yl]methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC(C=1C=C(C=CC=1)C=1C=C2C(=NC=1)NC(N2CC=1C=NC=CC=1C(F)(F)F)=O)(F)F RKKKAEBSWYCVKP-UHFFFAOYSA-N 0.000 claims 1
• LHBSNJHNCITXRY-UHFFFAOYSA-N 6-[3-(trifluoromethyl)phenyl]-1-[[5-(trifluoromethyl)pyridin-3-yl]methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC(C=1C=C(C=CC=1)C=1C=C2C(=NC=1)NC(N2CC=1C=NC=C(C=1)C(F)(F)F)=O)(F)F LHBSNJHNCITXRY-UHFFFAOYSA-N 0.000 claims 1
• NKFJSQSVVKJFHG-UHFFFAOYSA-N 6-[3-(trifluoromethyl)phenyl]-1-[[6-(trifluoromethyl)pyridin-3-yl]methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC(C=1C=C(C=CC=1)C=1C=C2C(=NC=1)NC(N2CC=1C=NC(=CC=1)C(F)(F)F)=O)(F)F NKFJSQSVVKJFHG-UHFFFAOYSA-N 0.000 claims 1
• WYSXKRXUPILXPX-UHFFFAOYSA-N 6-[3-fluoro-5-(trifluoromethyl)phenyl]-3-methyl-1-(pyridazin-3-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C=1C=C2C(=NC=1)N(C(N2CC=1N=NC=CC=1)=O)C WYSXKRXUPILXPX-UHFFFAOYSA-N 0.000 claims 1
• WGIDPSZCQIHBFG-UHFFFAOYSA-N 6-[4-(difluoromethyl)thiophen-2-yl]-1-[2-(3-fluoroazetidin-1-yl)-2-oxoethyl]-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound FC(C=1C=C(SC=1)C=1C=C2C(=NC=1)N(C(N2CC(=O)N1CC(C1)F)=O)C)F WGIDPSZCQIHBFG-UHFFFAOYSA-N 0.000 claims 1
• OILXIILSNDVDNP-UHFFFAOYSA-N 6-[4-chloro-3-(difluoromethoxy)phenyl]-1-[(5-fluoropyridin-3-yl)methyl]-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound ClC1=C(C=C(C=C1)C=1C=C2C(=NC=1)N(C(N2CC=1C=NC=C(C=1)F)=O)C)OC(F)F OILXIILSNDVDNP-UHFFFAOYSA-N 0.000 claims 1
• UDQKYUHUIJJCLM-UHFFFAOYSA-N 6-[4-chloro-3-(difluoromethoxy)phenyl]-3-methyl-1-(pyridazin-3-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound ClC1=C(C=C(C=C1)C=1C=C2C(=NC=1)N(C(N2CC=1N=NC=CC=1)=O)C)OC(F)F UDQKYUHUIJJCLM-UHFFFAOYSA-N 0.000 claims 1
• KTUGMSDFFMXBOL-UHFFFAOYSA-N 6-[4-chloro-3-(trifluoromethyl)phenyl]-3-methyl-1-(pyridazin-3-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound ClC1=C(C=C(C=C1)C=1C=C2C(=NC=1)N(C(N2CC=1N=NC=CC=1)=O)C)C(F)(F)F KTUGMSDFFMXBOL-UHFFFAOYSA-N 0.000 claims 1
• QYGREKRUKXTUHY-UHFFFAOYSA-N 6-[4-fluoro-3-(trifluoromethyl)phenyl]-1-(oxetan-2-ylmethyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound Fc1ccc(cc1C(F)(F)F)-c1cnc2[nH]c(=O)n(CC3CCO3)c2c1 QYGREKRUKXTUHY-UHFFFAOYSA-N 0.000 claims 1
• LMFFRPXHTJDAQD-UHFFFAOYSA-N 6-[4-fluoro-3-(trifluoromethyl)phenyl]-1-[(4-methylpyridin-3-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC=1C=NC=CC=1C)=O)C(F)(F)F LMFFRPXHTJDAQD-UHFFFAOYSA-N 0.000 claims 1
• ROYJZVPJMNDRBE-UHFFFAOYSA-N 6-[4-fluoro-3-(trifluoromethyl)phenyl]-1-[(5-methylpyridin-3-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)NC(N2CC=1C=NC=C(C=1)C)=O)C(F)(F)F ROYJZVPJMNDRBE-UHFFFAOYSA-N 0.000 claims 1
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