AU2016291158B2 - Substituted 4-azaindoles and their use as GluN2B receptor modulators - Google Patents

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Publication number

AU2016291158B2

AU2016291158B2 AU2016291158A AU2016291158A AU2016291158B2 AU 2016291158 B2 AU2016291158 B2 AU 2016291158B2 AU 2016291158 A AU2016291158 A AU 2016291158A AU 2016291158 A AU2016291158 A AU 2016291158A AU 2016291158 B2 AU2016291158 B2 AU 2016291158B2

Authority

AU

Australia

Prior art keywords

pyrrolo

pyridin

methyl

ethanone

fluoro

Prior art date

2015-07-09

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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• XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical class C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 title abstract description 19
• 108010054200 NR2B NMDA receptor Proteins 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 721
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 82
• 238000000034 method Methods 0.000 claims abstract description 57
• 201000010099 disease Diseases 0.000 claims abstract description 36
• 108010038912 Retinoid X Receptors Proteins 0.000 claims abstract description 31
• 230000000694 effects Effects 0.000 claims abstract description 23
• 230000001404 mediated effect Effects 0.000 claims abstract description 20
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 19
• 102000034527 Retinoid X Receptors Human genes 0.000 claims abstract 10
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 379
• VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 claims description 205
• -1 3-azabicyclo[3.1.0]hexan-3-yl Chemical group 0.000 claims description 172
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 133
• 125000005843 halogen group Chemical group 0.000 claims description 85
• 150000003839 salts Chemical class 0.000 claims description 85
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 82
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 69
• 239000012453 solvate Substances 0.000 claims description 50
• 208000035475 disorder Diseases 0.000 claims description 45
• 150000001204 N-oxides Chemical class 0.000 claims description 44
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 31
• 208000002193 Pain Diseases 0.000 claims description 28
• 125000001544 thienyl group Chemical group 0.000 claims description 25
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 23
• 125000004076 pyridyl group Chemical group 0.000 claims description 21
• 239000003814 drug Substances 0.000 claims description 20
• 229910052739 hydrogen Inorganic materials 0.000 claims description 17
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
• 230000001154 acute effect Effects 0.000 claims description 16
• 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 15
• 206010015037 epilepsy Diseases 0.000 claims description 14
• 229910052731 fluorine Inorganic materials 0.000 claims description 14
• 208000026106 cerebrovascular disease Diseases 0.000 claims description 13
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 13
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 10
• 229910052801 chlorine Inorganic materials 0.000 claims description 10
• 125000000335 thiazolyl group Chemical group 0.000 claims description 10
• 208000019901 Anxiety disease Diseases 0.000 claims description 9
• 230000036407 pain Effects 0.000 claims description 9
• DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 claims description 8
• 208000019022 Mood disease Diseases 0.000 claims description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
• 208000027520 Somatoform disease Diseases 0.000 claims description 7
• 230000001684 chronic effect Effects 0.000 claims description 7
• 230000004770 neurodegeneration Effects 0.000 claims description 7
• 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims description 6
• 208000020925 Bipolar disease Diseases 0.000 claims description 6
• 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 6
• 208000012661 Dyskinesia Diseases 0.000 claims description 6
• 125000002393 azetidinyl group Chemical group 0.000 claims description 6
• 206010008118 cerebral infarction Diseases 0.000 claims description 6
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
• 125000002541 furyl group Chemical group 0.000 claims description 6
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 6
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 6
• 125000002971 oxazolyl group Chemical group 0.000 claims description 6
• 125000003566 oxetanyl group Chemical group 0.000 claims description 6
• 125000000466 oxiranyl group Chemical group 0.000 claims description 6
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 6
• QGKLPGKXAVVPOJ-UHFFFAOYSA-N pyrrolidin-3-one Chemical compound O=C1CCNC1 QGKLPGKXAVVPOJ-UHFFFAOYSA-N 0.000 claims description 6
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 6
• 125000001425 triazolyl group Chemical group 0.000 claims description 6
• 208000028552 Treatment-Resistant Depressive disease Diseases 0.000 claims description 5
• 208000024714 major depressive disease Diseases 0.000 claims description 5
• 125000005936 piperidyl group Chemical group 0.000 claims description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
• QFXYCGGWYMINDD-UHFFFAOYSA-N 1-[6-(3,5-difluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]-3-methylbutan-2-one Chemical compound FC=1C=C(C=C(C=1)F)C=1C=C2C(=NC=1)C=CN2CC(C(C)C)=O QFXYCGGWYMINDD-UHFFFAOYSA-N 0.000 claims description 4
• MGOYXMNOVHUQCC-UHFFFAOYSA-N 2-[6-(4-fluoro-3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]acetic acid Chemical compound FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)C=CN2CC(=O)O)C MGOYXMNOVHUQCC-UHFFFAOYSA-N 0.000 claims description 4
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 4
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
• 208000024827 Alzheimer disease Diseases 0.000 claims description 4
• 208000023105 Huntington disease Diseases 0.000 claims description 4
• 208000012902 Nervous system 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
• 229910052794 bromium Inorganic materials 0.000 claims description 4
• 230000001667 episodic effect Effects 0.000 claims description 4
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 4
• 201000006417 multiple sclerosis Diseases 0.000 claims description 4
• 230000001314 paroxysmal effect Effects 0.000 claims description 4
• 125000003386 piperidinyl group Chemical group 0.000 claims description 4
• 208000020016 psychiatric disease Diseases 0.000 claims description 4
• 201000000980 schizophrenia Diseases 0.000 claims description 4
• ORCPXMQHRXZIPY-UHFFFAOYSA-N 1-(3-fluoroazetidin-1-yl)-2-[3-fluoro-6-(2-fluoro-3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1CN(C1)C(CN1C=C(C2=NC=C(C=C21)C1=C(C(=CC=C1)C)F)F)=O ORCPXMQHRXZIPY-UHFFFAOYSA-N 0.000 claims description 3
• IRCSHIHKAKVUQW-UHFFFAOYSA-N 1-(3-fluoroazetidin-1-yl)-2-[6-(2-fluoro-3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1CN(C1)C(CN1C=CC2=NC=C(C=C21)C1=C(C(=CC=C1)C)F)=O IRCSHIHKAKVUQW-UHFFFAOYSA-N 0.000 claims description 3
• BAJLKKDCRRARCS-UHFFFAOYSA-N 1-(4-fluorophenyl)-2-[6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1=CC=C(C=C1)C(CN1C=CC2=NC=C(C=C21)C1=CC=C(C=C1)F)=O BAJLKKDCRRARCS-UHFFFAOYSA-N 0.000 claims description 3
• BWSPUXIOIFPRIH-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-bromo-6-(4-fluoro-3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=CC(=C(C=C1)F)C)Br)=O BWSPUXIOIFPRIH-UHFFFAOYSA-N 0.000 claims description 3
• CODXZAGFAGSNLR-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-chloro-6-(4-fluoro-3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=CC(=C(C=C1)F)C)Cl)=O CODXZAGFAGSNLR-UHFFFAOYSA-N 0.000 claims description 3
• GUOMQVIAGVWUGW-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-chloro-6-[3-(trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)Cl)=O GUOMQVIAGVWUGW-UHFFFAOYSA-N 0.000 claims description 3
• SIOSWSXGBLWCHY-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=CC2=NC=C(C=C21)C1=CC=C(C=C1)F)=O SIOSWSXGBLWCHY-UHFFFAOYSA-N 0.000 claims description 3
• NNWNAHVVXRDDEN-UHFFFAOYSA-N 1-(pyridazin-3-ylmethyl)-6-[3-(trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridine Chemical compound N1=NC(=CC=C1)CN1C=CC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F NNWNAHVVXRDDEN-UHFFFAOYSA-N 0.000 claims description 3
• RAIQMPVQGITNBA-UHFFFAOYSA-N 1-[3-fluoro-6-(3-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]-3-methylbutan-2-one Chemical compound FC1=CN(C=2C1=NC=C(C=2)C1=CC(=CC=C1)F)CC(C(C)C)=O RAIQMPVQGITNBA-UHFFFAOYSA-N 0.000 claims description 3
• WPJPMOGYAKUTFH-UHFFFAOYSA-N 1-[3-fluoro-6-(4-fluoro-3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]-3-methylbutan-2-one Chemical compound FC1=CN(C=2C1=NC=C(C=2)C1=CC(=C(C=C1)F)C)CC(C(C)C)=O WPJPMOGYAKUTFH-UHFFFAOYSA-N 0.000 claims description 3
• HCYVXBRHOUIWSP-UHFFFAOYSA-N 1-[3-fluoro-6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]butan-2-one Chemical compound FC1=CN(C=2C1=NC=C(C=2)C1=CC=C(C=C1)F)CC(CC)=O HCYVXBRHOUIWSP-UHFFFAOYSA-N 0.000 claims description 3
• YZONMQPDOQAGQI-UHFFFAOYSA-N 1-[6-(3-ethylphenyl)-3-fluoropyrrolo[3,2-b]pyridin-1-yl]-3-methylbutan-2-one Chemical compound C(C)C=1C=C(C=CC=1)C=1C=C2C(=NC=1)C(=CN2CC(C(C)C)=O)F YZONMQPDOQAGQI-UHFFFAOYSA-N 0.000 claims description 3
• DSICMCNZSSQYOX-UHFFFAOYSA-N 1-[6-(3-ethylphenyl)pyrrolo[3,2-b]pyridin-1-yl]-3,3-dimethylbutan-2-one Chemical compound C(C)C=1C=C(C=CC=1)C=1C=C2C(=NC=1)C=CN2CC(C(C)(C)C)=O DSICMCNZSSQYOX-UHFFFAOYSA-N 0.000 claims description 3
• XUTNGXNXSZOSFF-UHFFFAOYSA-N 1-[6-(5-chlorothiophen-2-yl)-3-fluoropyrrolo[3,2-b]pyridin-1-yl]-3-methylbutan-2-one Chemical compound ClC1=CC=C(S1)C=1C=C2C(=NC=1)C(=CN2CC(C(C)C)=O)F XUTNGXNXSZOSFF-UHFFFAOYSA-N 0.000 claims description 3
• AYNZKPMWQUXKCK-UHFFFAOYSA-N 1-[6-[3-(difluoromethyl)phenyl]-3-fluoropyrrolo[3,2-b]pyridin-1-yl]butan-2-one Chemical compound FC(C=1C=C(C=CC=1)C=1C=C2C(=NC=1)C(=CN2CC(CC)=O)F)F AYNZKPMWQUXKCK-UHFFFAOYSA-N 0.000 claims description 3
• DZLMSOUHOZYOGY-UHFFFAOYSA-N 1-cyclopropyl-2-[3-fluoro-6-(4-fluoro-3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound C1(CC1)C(CN1C=C(C2=NC=C(C=C21)C1=CC(=C(C=C1)F)C)F)=O DZLMSOUHOZYOGY-UHFFFAOYSA-N 0.000 claims description 3
• OZVRPPLQVAASBC-UHFFFAOYSA-N 1-cyclopropyl-2-[6-(3-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound C1(CC1)C(CN1C=CC2=NC=C(C=C21)C1=CC(=CC=C1)F)=O OZVRPPLQVAASBC-UHFFFAOYSA-N 0.000 claims description 3
• IJOBPBAGYVHKKH-UHFFFAOYSA-N 1-cyclopropyl-2-[6-(3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound C1(CC1)C(CN1C=CC2=NC=C(C=C21)C=1C=C(C=CC=1)C)=O IJOBPBAGYVHKKH-UHFFFAOYSA-N 0.000 claims description 3
• GJKJZTUHYIDBNX-UHFFFAOYSA-N 1-cyclopropyl-2-[6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound C1(CC1)C(CN1C=CC2=NC=C(C=C21)C1=CC=C(C=C1)F)=O GJKJZTUHYIDBNX-UHFFFAOYSA-N 0.000 claims description 3
• WTNZRORTZPDRLP-UHFFFAOYSA-N 1-morpholin-4-yl-2-[6-(2,3,4-trifluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound O1CCN(CC1)C(CN1C=CC2=NC=C(C=C21)C1=C(C(=C(C=C1)F)F)F)=O WTNZRORTZPDRLP-UHFFFAOYSA-N 0.000 claims description 3
• JJIHOASQUBGCOO-UHFFFAOYSA-N 1-morpholin-4-yl-2-[6-(3,4,5-trifluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound O1CCN(CC1)C(CN1C=CC2=NC=C(C=C21)C1=CC(=C(C(=C1)F)F)F)=O JJIHOASQUBGCOO-UHFFFAOYSA-N 0.000 claims description 3
• AZUGKBZRBXGDML-UHFFFAOYSA-N 2-(3-chloro-6-phenylpyrrolo[3,2-b]pyridin-1-yl)-N,N-dimethylacetamide Chemical compound ClC1=CN(C=2C1=NC=C(C=2)C1=CC=CC=C1)CC(=O)N(C)C AZUGKBZRBXGDML-UHFFFAOYSA-N 0.000 claims description 3
• PDLYXBYCQYDPEK-UHFFFAOYSA-N 2-(3-chloro-6-phenylpyrrolo[3,2-b]pyridin-1-yl)-N-cyclopropylacetamide Chemical compound ClC1=CN(C=2C1=NC=C(C=2)C1=CC=CC=C1)CC(=O)NC1CC1 PDLYXBYCQYDPEK-UHFFFAOYSA-N 0.000 claims description 3
• LSMVSOSKGALZBD-UHFFFAOYSA-N 2-(3-fluoro-6-phenylpyrrolo[3,2-b]pyridin-1-yl)-N,N-dimethylacetamide Chemical compound FC1=CN(C=2C1=NC=C(C=2)C1=CC=CC=C1)CC(=O)N(C)C LSMVSOSKGALZBD-UHFFFAOYSA-N 0.000 claims description 3
• JGKSTUVYINBGDM-UHFFFAOYSA-N 2-[3-bromo-6-(3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]-1-morpholin-4-ylethanone Chemical compound BrC1=CN(C=2C1=NC=C(C=2)C=1C=C(C=CC=1)C)CC(=O)N1CCOCC1 JGKSTUVYINBGDM-UHFFFAOYSA-N 0.000 claims description 3
• UPLAXCIZZZJACT-UHFFFAOYSA-N 2-[3-bromo-6-(3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]-N-cyclopropylacetamide Chemical compound BrC1=CN(C=2C1=NC=C(C=2)C=1C=C(C=CC=1)C)CC(=O)NC1CC1 UPLAXCIZZZJACT-UHFFFAOYSA-N 0.000 claims description 3
• VHBCQVCPDLUWFR-UHFFFAOYSA-N 2-[3-chloro-6-(2-fluoro-3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]-N,N-dimethylacetamide Chemical compound ClC1=CN(C=2C1=NC=C(C=2)C1=C(C(=CC=C1)C)F)CC(=O)N(C)C VHBCQVCPDLUWFR-UHFFFAOYSA-N 0.000 claims description 3
• FLUISDBXJMAPMF-UHFFFAOYSA-N 2-[3-chloro-6-(4-fluoro-3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]-1-cyclobutylethanone Chemical compound ClC1=CN(C=2C1=NC=C(C=2)C1=CC(=C(C=C1)F)C)CC(=O)C1CCC1 FLUISDBXJMAPMF-UHFFFAOYSA-N 0.000 claims description 3
• SSZMZSYBOMQHAA-UHFFFAOYSA-N 2-[3-chloro-6-(4-fluoro-3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]-N,N-dimethylacetamide Chemical compound ClC1=CN(C=2C1=NC=C(C=2)C1=CC(=C(C=C1)F)C)CC(=O)N(C)C SSZMZSYBOMQHAA-UHFFFAOYSA-N 0.000 claims description 3
• GACQXHYZJOIPTE-UHFFFAOYSA-N 2-[3-chloro-6-(4-fluoro-3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]-N-cyclopropylacetamide 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.Cc1cc(ccc1F)-c1cnc2c(Cl)cn(CC(=O)NC3CC3)c2c1 GACQXHYZJOIPTE-UHFFFAOYSA-N 0.000 claims description 3
• YFABUVMCGFODFQ-UHFFFAOYSA-N 2-[3-chloro-6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]-1-morpholin-4-ylethanone Chemical compound ClC1=CN(C=2C1=NC=C(C=2)C1=CC=C(C=C1)F)CC(=O)N1CCOCC1 YFABUVMCGFODFQ-UHFFFAOYSA-N 0.000 claims description 3
• AYRXUZJFVMEMDD-UHFFFAOYSA-N 2-[3-chloro-6-(5-chloro-4-methylthiophen-2-yl)pyrrolo[3,2-b]pyridin-1-yl]-N,N-dimethylacetamide Chemical compound ClC1=CN(C=2C1=NC=C(C=2)C=1SC(=C(C=1)C)Cl)CC(=O)N(C)C AYRXUZJFVMEMDD-UHFFFAOYSA-N 0.000 claims description 3
• CBRPZDUTQPJAHS-UHFFFAOYSA-N 2-[3-chloro-6-(5-chlorothiophen-2-yl)pyrrolo[3,2-b]pyridin-1-yl]-N,N-dimethylacetamide Chemical compound ClC1=CN(C=2C1=NC=C(C=2)C=1SC(=CC=1)Cl)CC(=O)N(C)C CBRPZDUTQPJAHS-UHFFFAOYSA-N 0.000 claims description 3
• MXZCLWVFDFERQK-UHFFFAOYSA-N 2-[3-chloro-6-[5-(trifluoromethyl)thiophen-2-yl]pyrrolo[3,2-b]pyridin-1-yl]-N,N-dimethylacetamide Chemical compound ClC1=CN(C=2C1=NC=C(C=2)C=1SC(=CC=1)C(F)(F)F)CC(=O)N(C)C MXZCLWVFDFERQK-UHFFFAOYSA-N 0.000 claims description 3
• PIDQIGNSFDCHKF-UHFFFAOYSA-N 2-[3-fluoro-6-(4-fluoro-3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]-N,N-dimethylacetamide Chemical compound FC1=CN(C=2C1=NC=C(C=2)C1=CC(=C(C=C1)F)C)CC(=O)N(C)C PIDQIGNSFDCHKF-UHFFFAOYSA-N 0.000 claims description 3
• VYQAAMBBRDZTLU-UHFFFAOYSA-N 2-[3-fluoro-6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]-1-morpholin-4-ylethanone Chemical compound FC1=CN(C=2C1=NC=C(C=2)C1=CC=C(C=C1)F)CC(=O)N1CCOCC1 VYQAAMBBRDZTLU-UHFFFAOYSA-N 0.000 claims description 3
• IUNAXXOGRFMFOP-UHFFFAOYSA-N 2-[3-fluoro-6-(4-methylthiophen-2-yl)pyrrolo[3,2-b]pyridin-1-yl]-N,N-dimethylacetamide Chemical compound FC1=CN(C=2C1=NC=C(C=2)C=1SC=C(C=1)C)CC(=O)N(C)C IUNAXXOGRFMFOP-UHFFFAOYSA-N 0.000 claims description 3
• BVPZFCFQMATRFR-UHFFFAOYSA-N 2-[3-fluoro-6-(5-methylthiophen-2-yl)pyrrolo[3,2-b]pyridin-1-yl]-N,N-dimethylacetamide Chemical compound FC1=CN(C=2C1=NC=C(C=2)C=1SC(=CC=1)C)CC(=O)N(C)C BVPZFCFQMATRFR-UHFFFAOYSA-N 0.000 claims description 3
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• VQQVMPBMCSOUDZ-UHFFFAOYSA-N 1-(3-fluoroazetidin-1-yl)-2-[6-(2-fluorophenyl)-3-methylpyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1CN(C1)C(CN1C=C(C2=NC=C(C=C21)C1=C(C=CC=C1)F)C)=O VQQVMPBMCSOUDZ-UHFFFAOYSA-N 0.000 claims 1
• CKALXNVJTHAMFW-UHFFFAOYSA-N 1-(3-fluoroazetidin-1-yl)-2-[6-(4-fluoro-2-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.FC1CN(C1)C(CN1C=CC2=NC=C(C=C21)C2=C(C=C(C=C2)F)C)=O CKALXNVJTHAMFW-UHFFFAOYSA-N 0.000 claims 1
• WFCPRJXUOBJBNG-UHFFFAOYSA-N 1-(3-fluoroazetidin-1-yl)-2-[6-(4-fluoro-3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1CN(C1)C(CN1C=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C)=O WFCPRJXUOBJBNG-UHFFFAOYSA-N 0.000 claims 1
• ISABPYRXZSTPIF-UHFFFAOYSA-N 1-(3-fluoroazetidin-1-yl)-2-[6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1CN(C1)C(CN1C=CC2=NC=C(C=C21)C1=CC=C(C=C1)F)=O ISABPYRXZSTPIF-UHFFFAOYSA-N 0.000 claims 1
• ZPCQZCWZFXVGNI-UHFFFAOYSA-N 1-(3-fluoroazetidin-1-yl)-2-[6-(4-methylthiophen-2-yl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1CN(C1)C(CN1C=CC2=NC=C(C=C21)C=1SC=C(C=1)C)=O ZPCQZCWZFXVGNI-UHFFFAOYSA-N 0.000 claims 1
• XMYYXKVBKRCNSM-UHFFFAOYSA-N 1-(3-fluoroazetidin-1-yl)-2-[6-[2-fluoro-3-(trifluoromethyl)phenyl]-3-methylpyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1CN(C1)C(CN1C=C(C2=NC=C(C=C21)C1=C(C(=CC=C1)C(F)(F)F)F)C)=O XMYYXKVBKRCNSM-UHFFFAOYSA-N 0.000 claims 1
• LXZZTHBQWMYMIU-UHFFFAOYSA-N 1-(3-fluoroazetidin-1-yl)-2-[6-[2-fluoro-3-(trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1CN(C1)C(=O)CN1C=CC2=NC=C(C=C12)C1=CC=CC(=C1F)C(F)(F)F LXZZTHBQWMYMIU-UHFFFAOYSA-N 0.000 claims 1
• IJXVSBAQOGNXTN-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-(6-phenylpyrrolo[3,2-b]pyridin-1-yl)ethanone Chemical compound N1(CCC1)C(CN1C=CC2=NC=C(C=C21)C1=CC=CC=C1)=O IJXVSBAQOGNXTN-UHFFFAOYSA-N 0.000 claims 1
• GHEPHHYAAKFKOD-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[2-methyl-6-(3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C(=CC2=NC=C(C=C21)C=1C=C(C=CC=1)C)C)=O GHEPHHYAAKFKOD-UHFFFAOYSA-N 0.000 claims 1
• BGBYJFQGRKPFMA-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-bromo-6-(3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C=1C=C(C=CC=1)C)Br)=O BGBYJFQGRKPFMA-UHFFFAOYSA-N 0.000 claims 1
• GDTJBAZUWDUJCA-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-bromo-6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=CC=C(C=C1)F)Br)=O GDTJBAZUWDUJCA-UHFFFAOYSA-N 0.000 claims 1
• ZYKFBRUNVPGZSG-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-chloro-6-(2,3,4-trifluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=C(C(=C(C=C1)F)F)F)Cl)=O ZYKFBRUNVPGZSG-UHFFFAOYSA-N 0.000 claims 1
• VXXWEFWANDGLTP-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-chloro-6-(2,4-difluoro-3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=C(C(=C(C=C1)F)C)F)Cl)=O VXXWEFWANDGLTP-UHFFFAOYSA-N 0.000 claims 1
• UFSKYTGDHOCFBX-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-chloro-6-(2-fluoro-3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=C(C(=CC=C1)C)F)Cl)=O UFSKYTGDHOCFBX-UHFFFAOYSA-N 0.000 claims 1
• JXPDOILCMKBFLY-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-chloro-6-(2-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=C(C=CC=C1)F)Cl)=O JXPDOILCMKBFLY-UHFFFAOYSA-N 0.000 claims 1
• QOWLNGATIZGHPT-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-chloro-6-(3,4,5-trifluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=CC(=C(C(=C1)F)F)F)Cl)=O QOWLNGATIZGHPT-UHFFFAOYSA-N 0.000 claims 1
• JVAASQADCGGFNG-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-chloro-6-(3,4-difluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=CC(=C(C=C1)F)F)Cl)=O JVAASQADCGGFNG-UHFFFAOYSA-N 0.000 claims 1
• QKPLYEIYNJHDNI-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-chloro-6-(3,5-dimethylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=CC(=CC(=C1)C)C)Cl)=O QKPLYEIYNJHDNI-UHFFFAOYSA-N 0.000 claims 1
• QLKZOKSTSHZSAV-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-chloro-6-(3-chloro-2-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=C(C(=CC=C1)Cl)F)Cl)=O QLKZOKSTSHZSAV-UHFFFAOYSA-N 0.000 claims 1
• VPAYMQHMNORWOM-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-chloro-6-(3-chloro-4-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=CC(=C(C=C1)F)Cl)Cl)=O VPAYMQHMNORWOM-UHFFFAOYSA-N 0.000 claims 1
• WHTZHMMCYNEKSK-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-chloro-6-(3-chlorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=CC(=CC=C1)Cl)Cl)=O WHTZHMMCYNEKSK-UHFFFAOYSA-N 0.000 claims 1
• APBMYHJBJAIEAV-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-chloro-6-(3-ethylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=CC(=CC=C1)CC)Cl)=O APBMYHJBJAIEAV-UHFFFAOYSA-N 0.000 claims 1
• HRRRJAMZNIIXMP-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-chloro-6-(3-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=CC(=CC=C1)F)Cl)=O HRRRJAMZNIIXMP-UHFFFAOYSA-N 0.000 claims 1
• GAEZLRYKLBRVGZ-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-chloro-6-(3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C=1C=C(C=CC=1)C)Cl)=O GAEZLRYKLBRVGZ-UHFFFAOYSA-N 0.000 claims 1
• KJMJZRGVFRRAFE-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-chloro-6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=CC=C(C=C1)F)Cl)=O KJMJZRGVFRRAFE-UHFFFAOYSA-N 0.000 claims 1
• VCWZBXFSYKLOIL-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-chloro-6-(5-chlorothiophen-2-yl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C=1SC(=CC=1)Cl)Cl)=O VCWZBXFSYKLOIL-UHFFFAOYSA-N 0.000 claims 1
• BFIXEJMWJMSWJZ-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-fluoro-6-(2,3,4-trifluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=C(C(=C(C=C1)F)F)F)F)=O BFIXEJMWJMSWJZ-UHFFFAOYSA-N 0.000 claims 1
• HSJZEHSJRVMHSJ-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-fluoro-6-(3,4,5-trifluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=CC(=C(C(=C1)F)F)F)F)=O HSJZEHSJRVMHSJ-UHFFFAOYSA-N 0.000 claims 1
• ASOWYWMVMNWJGM-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-fluoro-6-(3-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=CC(=CC=C1)F)F)=O ASOWYWMVMNWJGM-UHFFFAOYSA-N 0.000 claims 1
• CAZNUSSNKAWVID-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-fluoro-6-(3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C=1C=C(C=CC=1)C)F)=O CAZNUSSNKAWVID-UHFFFAOYSA-N 0.000 claims 1
• HIPMQNZRIDKJFA-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-fluoro-6-(4-fluoro-3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=CC(=C(C=C1)F)C)F)=O HIPMQNZRIDKJFA-UHFFFAOYSA-N 0.000 claims 1
• RTZJHSPXRNKTIS-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-fluoro-6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=CC=C(C=C1)F)F)=O RTZJHSPXRNKTIS-UHFFFAOYSA-N 0.000 claims 1
• KKQSFMXBXCOGOC-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-fluoro-6-(4-methylthiophen-2-yl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C=1SC=C(C=1)C)F)=O KKQSFMXBXCOGOC-UHFFFAOYSA-N 0.000 claims 1
• AFCZXHULRUDASA-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-fluoro-6-[3-(trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)F)=O AFCZXHULRUDASA-UHFFFAOYSA-N 0.000 claims 1
• PTCIRQZELHQLJH-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-methyl-6-(3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C=1C=C(C=CC=1)C)C)=O PTCIRQZELHQLJH-UHFFFAOYSA-N 0.000 claims 1
• BAFLKDXDZXIENT-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-methyl-6-(5-methylthiophen-2-yl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C=1SC(=CC=1)C)C)=O BAFLKDXDZXIENT-UHFFFAOYSA-N 0.000 claims 1
• IKULXLSBUQXWRJ-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-methyl-6-[3-(trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)C)=O IKULXLSBUQXWRJ-UHFFFAOYSA-N 0.000 claims 1
• AITCJMKMFKKUQE-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(2,3,4-trifluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=CC2=NC=C(C=C21)C1=C(C(=C(C=C1)F)F)F)=O AITCJMKMFKKUQE-UHFFFAOYSA-N 0.000 claims 1
• VHPVZCCATOMNAI-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(2,4-difluoro-3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=CC2=NC=C(C=C21)C1=C(C(=C(C=C1)F)C)F)=O VHPVZCCATOMNAI-UHFFFAOYSA-N 0.000 claims 1
• FVRDCAWWXPEYEC-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(2-fluoro-3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=CC2=NC=C(C=C21)C1=C(C(=CC=C1)C)F)=O FVRDCAWWXPEYEC-UHFFFAOYSA-N 0.000 claims 1
• AODQLLMCKBWLJK-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(2-fluorophenyl)-3-methylpyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=C(C=CC=C1)F)C)=O AODQLLMCKBWLJK-UHFFFAOYSA-N 0.000 claims 1
• CETKFEIBWAFBQM-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(3,4,5-trifluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=CC2=NC=C(C=C21)C1=CC(=C(C(=C1)F)F)F)=O CETKFEIBWAFBQM-UHFFFAOYSA-N 0.000 claims 1
• WEYZIUWUTVLJAG-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(3,4-difluorophenyl)-3-methylpyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=CC(=C(C=C1)F)F)C)=O WEYZIUWUTVLJAG-UHFFFAOYSA-N 0.000 claims 1
• LFDLOIYSPXYQTM-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(3,5-difluorophenyl)-3-fluoropyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=CC(=CC(=C1)F)F)F)=O LFDLOIYSPXYQTM-UHFFFAOYSA-N 0.000 claims 1
• NGUYFTRPVOROHN-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(3,5-difluorophenyl)-3-methylpyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=CC(=CC(=C1)F)F)C)=O NGUYFTRPVOROHN-UHFFFAOYSA-N 0.000 claims 1
• HUDUFYULTOHLQZ-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(3-chloro-2-fluorophenyl)-3-fluoropyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=C(C(=CC=C1)Cl)F)F)=O HUDUFYULTOHLQZ-UHFFFAOYSA-N 0.000 claims 1
• ZTWUXNZNCZPYTA-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(3-chloro-2-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=CC2=NC=C(C=C21)C1=C(C(=CC=C1)Cl)F)=O ZTWUXNZNCZPYTA-UHFFFAOYSA-N 0.000 claims 1
• WHVSGZWDSUCTOA-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(3-chloro-4-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)Cl)=O WHVSGZWDSUCTOA-UHFFFAOYSA-N 0.000 claims 1
• NGBWYQCBVBZQKE-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(3-chlorophenyl)-3-fluoropyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=CC(=CC=C1)Cl)F)=O NGBWYQCBVBZQKE-UHFFFAOYSA-N 0.000 claims 1
• LZIYKUJNFOMIHT-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(3-chlorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=CC2=NC=C(C=C21)C1=CC(=CC=C1)Cl)=O LZIYKUJNFOMIHT-UHFFFAOYSA-N 0.000 claims 1
• QGZRQRQVPCZUPG-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(4-fluoro-2,3-dimethylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.N1(CCC1)C(CN1C=CC2=NC=C(C=C21)C2=C(C(=C(C=C2)F)C)C)=O QGZRQRQVPCZUPG-UHFFFAOYSA-N 0.000 claims 1
• COAKUMUNGWFMEY-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(4-fluoro-2-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.N1(CCC1)C(CN1C=CC2=NC=C(C=C21)C2=C(C=C(C=C2)F)C)=O COAKUMUNGWFMEY-UHFFFAOYSA-N 0.000 claims 1
• QDEAMLSUQRZWCI-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(4-fluorophenyl)-2-methylpyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C(=CC2=NC=C(C=C21)C1=CC=C(C=C1)F)C)=O QDEAMLSUQRZWCI-UHFFFAOYSA-N 0.000 claims 1
• WUCYOKPEOYZVIK-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(4-fluorophenyl)-3-methylpyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=CC=C(C=C1)F)C)=O WUCYOKPEOYZVIK-UHFFFAOYSA-N 0.000 claims 1
• FJXRETFWDMKZRA-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(5-chlorothiophen-2-yl)-3-fluoropyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C=1SC(=CC=1)Cl)F)=O FJXRETFWDMKZRA-UHFFFAOYSA-N 0.000 claims 1
• LKLTWPOKHJVUEQ-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(5-chlorothiophen-2-yl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=CC2=NC=C(C=C21)C=1SC(=CC=1)Cl)=O LKLTWPOKHJVUEQ-UHFFFAOYSA-N 0.000 claims 1
• AHLOXMOMKJWPBD-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-[2-(trifluoromethyl)pyridin-4-yl]pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=CC2=NC=C(C=C21)C1=CC(=NC=C1)C(F)(F)F)=O AHLOXMOMKJWPBD-UHFFFAOYSA-N 0.000 claims 1
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• 229910052725 zinc Inorganic materials 0.000 description 1
• 239000011701 zinc Substances 0.000 description 1