AU2017340602A1 - Substituted 1H-imidazo[4,5-b]pyridin-2(3H)-ones and their use as GluN2B receptor modulators - Google Patents

Info

Publication number

AU2017340602A1

AU2017340602A1 AU2017340602A AU2017340602A AU2017340602A1 AU 2017340602 A1 AU2017340602 A1 AU 2017340602A1 AU 2017340602 A AU2017340602 A AU 2017340602A AU 2017340602 A AU2017340602 A AU 2017340602A AU 2017340602 A1 AU2017340602 A1 AU 2017340602A1

Authority

AU

Australia

Prior art keywords

pyridin

imidazo

methyl

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.)

Abandoned

Links

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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 description 3
• 108010054200 NR2B NMDA receptor Proteins 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 510
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 68
• 238000000034 method Methods 0.000 claims abstract description 45
• 201000010099 disease Diseases 0.000 claims abstract description 30
• 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 3,5-Dimethoxyphenyl Chemical group 0.000 claims description 427
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 282
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 273
• 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 234
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 198
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 100
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 70
• 150000003839 salts Chemical class 0.000 claims description 70
• 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 claims description 64
• 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 claims description 64
• 125000004076 pyridyl group Chemical group 0.000 claims description 52
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 49
• 125000001544 thienyl group Chemical group 0.000 claims description 45
• 125000005843 halogen group Chemical group 0.000 claims description 43
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 39
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 37
• 208000035475 disorder Diseases 0.000 claims description 37
• 239000012453 solvate Substances 0.000 claims description 35
• 125000003566 oxetanyl group Chemical group 0.000 claims description 32
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 32
• 150000001204 N-oxides Chemical class 0.000 claims description 27
• 208000002193 Pain Diseases 0.000 claims description 27
• 125000000335 thiazolyl group Chemical group 0.000 claims description 27
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 25
• 125000002393 azetidinyl group Chemical group 0.000 claims description 23
• 229910052731 fluorine Inorganic materials 0.000 claims description 23
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 23
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 20
• 229910052801 chlorine Inorganic materials 0.000 claims description 19
• 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 14
• 206010015037 epilepsy Diseases 0.000 claims description 13
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 12
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 11
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 10
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 10
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 10
• FPGGLMIYNLQOID-UHFFFAOYSA-N 3h-pyridin-2-one Chemical compound O=C1CC=CC=N1 FPGGLMIYNLQOID-UHFFFAOYSA-N 0.000 claims description 9
• 208000020925 Bipolar disease Diseases 0.000 claims description 9
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 9
• 125000001425 triazolyl group Chemical group 0.000 claims description 9
• 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
• VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 8
• 125000000623 heterocyclic group Chemical group 0.000 claims description 8
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 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
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 8
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 8
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
• 208000028552 Treatment-Resistant Depressive disease Diseases 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
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 6
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 6
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
• 208000020706 Autistic disease 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
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 6
• 125000004193 piperazinyl group Chemical group 0.000 claims description 6
• 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 6
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 5
• 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 5
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 5
• 229940113088 dimethylacetamide Drugs 0.000 claims description 5
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
• 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
• 208000023105 Huntington disease 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
• 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 description 3
• 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 description 3
• 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 description 3
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 3
• 125000001188 haloalkyl group Chemical group 0.000 claims description 3
• 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 3
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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
• 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 description 2
• 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 description 2
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])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
• FZYMTQLTKSNJCC-UHFFFAOYSA-N 3-[[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(N2CC=1C=C(C#N)C=CC=1)=O FZYMTQLTKSNJCC-UHFFFAOYSA-N 0.000 claims description 2
• RQNUPXQOAMOOCM-UHFFFAOYSA-N 3-methyl-1-[(3-methyl-1,2,4-oxadiazol-5-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=NC(=NO1)C)=O RQNUPXQOAMOOCM-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• SRXONDLYPKGMFB-UHFFFAOYSA-N 6-(2,4-difluoro-3-methylphenyl)-3-methyl-1-(pyrazin-2-ylmethyl)imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=CC(=C1C)F)C=1C=C2C(=NC=1)N(C(N2CC1=NC=CN=C1)=O)C SRXONDLYPKGMFB-UHFFFAOYSA-N 0.000 claims description 2
• LDJCHFSAEHEGQW-UHFFFAOYSA-N 6-(2,4-difluorophenyl)-1-[(1-methylpyrazol-3-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C=CC(=C1)F)C=1C=C2C(=NC=1)NC(N2CC1=NN(C=C1)C)=O LDJCHFSAEHEGQW-UHFFFAOYSA-N 0.000 claims description 2
• RBOUKAABEJLBLU-UHFFFAOYSA-N 6-(2-ethoxyphenyl)-1-[(3-methoxyphenyl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound C(C)OC1=C(C=CC=C1)C=1C=C2C(=NC=1)NC(N2CC1=CC(=CC=C1)OC)=O RBOUKAABEJLBLU-UHFFFAOYSA-N 0.000 claims description 2
• FFBJODSMWBHFLA-UHFFFAOYSA-N 6-(2-methylphenyl)-1-(2-pyrrolidin-1-ylethyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound C1(=C(C=CC=C1)C=1C=C2C(=NC=1)NC(N2CCN1CCCC1)=O)C FFBJODSMWBHFLA-UHFFFAOYSA-N 0.000 claims description 2
• QMRZQRNXULPUNB-UHFFFAOYSA-N 6-(3,4-difluorophenyl)-1-[(1-methylpyrazol-3-yl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound FC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)NC(N2CC1=NN(C=C1)C)=O QMRZQRNXULPUNB-UHFFFAOYSA-N 0.000 claims description 2
• WWNNHJQGPZMYAD-UHFFFAOYSA-N 6-(3,4-difluorophenyl)-1-[2-(3-fluoroazetidin-1-yl)-2-oxoethyl]-3-methylimidazo[4,5-b]pyridin-2-one Chemical compound FC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)N(C(N2CC(=O)N1CC(C1)F)=O)C WWNNHJQGPZMYAD-UHFFFAOYSA-N 0.000 claims description 2
• ASOSWPLBVZAQSI-UHFFFAOYSA-N 6-(3,4-difluorophenyl)-3-methyl-1-[(1-methylpyrazol-4-yl)methyl]imidazo[4,5-b]pyridin-2-one Chemical compound FC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)N(C(N2CC=1C=NN(C=1)C)=O)C ASOSWPLBVZAQSI-UHFFFAOYSA-N 0.000 claims description 2
• AEALSKZSJNBYQA-UHFFFAOYSA-N 6-(3,5-difluorophenyl)-1-[(4-methoxyphenyl)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(N2CC1=CC=C(C=C1)OC)=O AEALSKZSJNBYQA-UHFFFAOYSA-N 0.000 claims description 2
• XFVBGWAFKYUCFK-UHFFFAOYSA-N 6-(3,5-difluorophenyl)-1-[2-(propylamino)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(N2CCNCCC)=O XFVBGWAFKYUCFK-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• WGLGFZATXZJAGJ-UHFFFAOYSA-N 6-(3-methoxyphenyl)-1-(pyridin-2-ylmethyl)-3H-imidazo[4,5-b]pyridin-2-one Chemical compound COC=1C=C(C=CC=1)C=1C=C2C(=NC=1)NC(N2CC1=NC=CC=C1)=O WGLGFZATXZJAGJ-UHFFFAOYSA-N 0.000 claims description 2
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