KR20180026760A - 치환된 4-아자인돌 및 glun2b 수용체 조절제로서의 이의 용도 - Google Patents

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Publication number

KR20180026760A

KR20180026760A KR1020187003560A KR20187003560A KR20180026760A KR 20180026760 A KR20180026760 A KR 20180026760A KR 1020187003560 A KR1020187003560 A KR 1020187003560A KR 20187003560 A KR20187003560 A KR 20187003560A KR 20180026760 A KR20180026760 A KR 20180026760A

Authority

KR

South Korea

Prior art keywords

pyrrolo

pyridin

ethanone

methyl

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.)

Withdrawn

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• 108010054200 NR2B NMDA receptor Proteins 0.000 title claims 3
• XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical class C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 title abstract description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 774
• 238000000034 method Methods 0.000 claims abstract description 347
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 94
• 208000035475 disorder Diseases 0.000 claims abstract description 61
• 201000010099 disease Diseases 0.000 claims abstract description 33
• 108010038912 Retinoid X Receptors Proteins 0.000 claims abstract description 27
• 230000001404 mediated effect Effects 0.000 claims abstract description 19
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 19
• 230000000694 effects Effects 0.000 claims abstract description 18
• -1 3-azabicyclo [3.1.0] hexan-3-yl Chemical group 0.000 claims description 396
• 125000000217 alkyl group Chemical group 0.000 claims description 183
• 125000005843 halogen group Chemical group 0.000 claims description 95
• 150000003839 salts Chemical class 0.000 claims description 71
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 70
• 125000001188 haloalkyl group Chemical group 0.000 claims description 66
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 62
• 229910052739 hydrogen Inorganic materials 0.000 claims description 50
• 229910052757 nitrogen Inorganic materials 0.000 claims description 49
• 229910052799 carbon Inorganic materials 0.000 claims description 37
• LPIURYDEKDUCPE-UHFFFAOYSA-N acetaldehyde 2,2,2-trifluoroacetic acid Chemical compound CC=O.OC(=O)C(F)(F)F LPIURYDEKDUCPE-UHFFFAOYSA-N 0.000 claims description 35
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 35
• 206010015037 epilepsy Diseases 0.000 claims description 35
• 125000003545 alkoxy group Chemical group 0.000 claims description 32
• 239000012453 solvate Substances 0.000 claims description 30
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 28
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 26
• 102100022630 Glutamate receptor ionotropic, NMDA 2B Human genes 0.000 claims description 26
• 150000001204 N-oxides Chemical class 0.000 claims description 25
• 125000004076 pyridyl group Chemical group 0.000 claims description 25
• 125000001544 thienyl group Chemical group 0.000 claims description 25
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
• OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 23
• 230000001154 acute effect Effects 0.000 claims description 21
• 208000002193 Pain Diseases 0.000 claims description 20
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 18
• 229910052731 fluorine Inorganic materials 0.000 claims description 17
• 208000018737 Parkinson disease Diseases 0.000 claims description 15
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 13
• 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 13
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 13
• 208000011580 syndromic disease Diseases 0.000 claims description 13
• 229910052801 chlorine Inorganic materials 0.000 claims description 12
• 239000007787 solid Substances 0.000 claims description 12
• 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 claims description 11
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 11
• 125000000335 thiazolyl group Chemical group 0.000 claims description 11
• 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 10
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 10
• 208000019022 Mood disease Diseases 0.000 claims description 10
• 208000026106 cerebrovascular disease Diseases 0.000 claims description 10
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 10
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
• 230000001225 therapeutic effect Effects 0.000 claims description 8
• AINOTODHGHVTEE-UHFFFAOYSA-N 3-fluoroazetidin-2-one Chemical compound FC1CNC1=O AINOTODHGHVTEE-UHFFFAOYSA-N 0.000 claims description 7
• 208000019901 Anxiety disease Diseases 0.000 claims description 7
• 208000020706 Autistic disease Diseases 0.000 claims description 7
• 208000027520 Somatoform disease Diseases 0.000 claims description 7
• 125000002541 furyl group Chemical group 0.000 claims description 7
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 7
• 125000002971 oxazolyl group Chemical group 0.000 claims description 7
• 125000003566 oxetanyl group Chemical group 0.000 claims description 7
• 125000000466 oxiranyl group Chemical group 0.000 claims description 7
• 125000003386 piperidinyl group Chemical group 0.000 claims description 7
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 7
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
• 125000001412 tetrahydropyranyl 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 6
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
• 206010003805 Autism Diseases 0.000 claims description 6
• 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 6
• 230000001684 chronic effect Effects 0.000 claims description 6
• 125000002496 methyl group Chemical group [H]C([H])([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 5
• ZLFHWHHHXXMPEY-UHFFFAOYSA-N 3-methyl-1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CN=C2C(C)=CNC2=C1 ZLFHWHHHXXMPEY-UHFFFAOYSA-N 0.000 claims description 5
• 208000012239 Developmental disease Diseases 0.000 claims description 5
• 208000019430 Motor disease Diseases 0.000 claims description 5
• 208000006011 Stroke Diseases 0.000 claims description 5
• 208000024714 major depressive disease Diseases 0.000 claims description 5
• 230000004770 neurodegeneration Effects 0.000 claims description 5
• 238000002360 preparation method Methods 0.000 claims description 5
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 4
• 208000020925 Bipolar disease Diseases 0.000 claims description 4
• 208000012661 Dyskinesia Diseases 0.000 claims description 4
• 159000000021 acetate salts Chemical class 0.000 claims description 4
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 4
• 230000003542 behavioural effect Effects 0.000 claims description 4
• 229910052794 bromium Inorganic materials 0.000 claims description 4
• 206010014599 encephalitis Diseases 0.000 claims description 4
• 230000015654 memory Effects 0.000 claims description 4
• 201000006417 multiple sclerosis Diseases 0.000 claims description 4
• 230000000926 neurological effect Effects 0.000 claims description 4
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 4
• 239000001301 oxygen Substances 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 230000036407 pain Effects 0.000 claims description 4
• 201000000980 schizophrenia Diseases 0.000 claims description 4
• BGPISVGEPLIPAP-UHFFFAOYSA-N 1-morpholin-4-yl-2-(6-phenylpyrrolo[3,2-b]pyridin-1-yl)ethanone Chemical compound O1CCN(CC1)C(CN1C=CC2=NC=C(C=C21)C1=CC=CC=C1)=O BGPISVGEPLIPAP-UHFFFAOYSA-N 0.000 claims description 3
• VDSCYBRUGKEJAI-UHFFFAOYSA-N 2-(3-bromo-6-phenylpyrrolo[3,2-b]pyridin-1-yl)-N-cyclopropylacetamide Chemical compound BrC1=CN(C=2C1=NC=C(C=2)C1=CC=CC=C1)CC(=O)NC1CC1 VDSCYBRUGKEJAI-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
• NGLLRIOSKTZPSP-UHFFFAOYSA-N 2-(6-phenylpyrrolo[3,2-b]pyridin-1-yl)-1-pyrrolidin-1-ylethanone Chemical compound C1(=CC=CC=C1)C=1C=C2C(=NC=1)C=CN2CC(=O)N1CCCC1 NGLLRIOSKTZPSP-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• IBMIJAYYMKMULD-UHFFFAOYSA-N 2-[6-(4-fluorophenyl)-2-methylpyrrolo[3,2-b]pyridin-1-yl]-1-morpholin-4-ylethanone Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=1)C=C(N2CC(=O)N1CCOCC1)C IBMIJAYYMKMULD-UHFFFAOYSA-N 0.000 claims description 3
• KYNVTOIPYGYOEL-UHFFFAOYSA-N 2-[6-(4-fluorophenyl)-3-methylpyrrolo[3,2-b]pyridin-1-yl]-1-pyrrolidin-1-ylethanone Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=1)C(=CN2CC(=O)N1CCCC1)C KYNVTOIPYGYOEL-UHFFFAOYSA-N 0.000 claims description 3
• GBFUOUAJDDZYON-UHFFFAOYSA-N 2-[6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]-1-phenylethanone Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=1)C=CN2CC(=O)C1=CC=CC=C1 GBFUOUAJDDZYON-UHFFFAOYSA-N 0.000 claims description 3
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• QUHVRXKSQHIZNV-UHFFFAOYSA-N 3,3-difluoroazetidine Chemical compound FC1(F)CNC1 QUHVRXKSQHIZNV-UHFFFAOYSA-N 0.000 claims description 3
• MUAWFFRNASLULC-UHFFFAOYSA-N 6-(3,4-difluorophenyl)-1-[(5-fluoropyrimidin-2-yl)methyl]pyrrolo[3,2-b]pyridine Chemical compound FC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=CN2CC1=NC=C(C=N1)F MUAWFFRNASLULC-UHFFFAOYSA-N 0.000 claims description 3
• NLSAPISKMYKKKS-UHFFFAOYSA-N 6-(4-methylthiophen-2-yl)-1-(pyridazin-3-ylmethyl)pyrrolo[3,2-b]pyridine Chemical compound CC=1C=C(SC=1)C=1C=C2C(=NC=1)C=CN2CC=1N=NC=CC=1 NLSAPISKMYKKKS-UHFFFAOYSA-N 0.000 claims description 3
• 208000024827 Alzheimer disease Diseases 0.000 claims description 3
• 208000023105 Huntington disease Diseases 0.000 claims description 3
• 208000018300 basal ganglia disease Diseases 0.000 claims description 3
• 206010008118 cerebral infarction Diseases 0.000 claims description 3
• 239000012230 colorless oil Substances 0.000 claims description 3
• 239000013078 crystal Substances 0.000 claims description 3
• 230000000626 neurodegenerative effect Effects 0.000 claims description 3
• FTKAKNPCUQUWQA-UHFFFAOYSA-N 1-(3-fluoroazetidin-1-yl)-2-(6-thiophen-2-ylpyrrolo[3,2-b]pyridin-1-yl)ethanone Chemical compound FC1CN(C1)C(CN1C=CC2=NC=C(C=C21)C=1SC=CC=1)=O FTKAKNPCUQUWQA-UHFFFAOYSA-N 0.000 claims description 2
• ZGABRCPGLRVDQL-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-(3-chloro-6-thiophen-2-ylpyrrolo[3,2-b]pyridin-1-yl)ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C=1SC=CC=1)Cl)=O ZGABRCPGLRVDQL-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• YKIWEUCLGQRMNC-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-(6-thiophen-2-ylpyrrolo[3,2-b]pyridin-1-yl)ethanone Chemical compound N1(CCC1)C(CN1C=CC2=NC=C(C=C21)C=1SC=CC=1)=O YKIWEUCLGQRMNC-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• XHZQBINWYJHYIZ-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(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)F)=O XHZQBINWYJHYIZ-UHFFFAOYSA-N 0.000 claims description 2
• IHSLMVCZWACYGF-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(2-methyl-1,3-thiazol-5-yl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=CC2=NC=C(C=C21)C1=CN=C(S1)C)=O IHSLMVCZWACYGF-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• JHZCAEXICAAXCT-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(3,5-difluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=CC2=NC=C(C=C21)C1=CC(=CC(=C1)F)F)=O JHZCAEXICAAXCT-UHFFFAOYSA-N 0.000 claims description 2
• HLZYXZSGZOMORR-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(3-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=1Cl)=O HLZYXZSGZOMORR-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 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 description 2
• VNISWBAIIKGROK-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(5-methylthiophen-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)C)=O VNISWBAIIKGROK-UHFFFAOYSA-N 0.000 claims description 2
• WULXPALUHGSGCY-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(6-fluoropyridin-3-yl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=CC2=NC=C(C=C21)C=1C=NC(=CC=1)F)=O WULXPALUHGSGCY-UHFFFAOYSA-N 0.000 claims description 2
• KAKJDCJMDMWKQS-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(6-methylpyridin-3-yl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=CC2=NC=C(C=C21)C=1C=NC(=CC=1)C)=O KAKJDCJMDMWKQS-UHFFFAOYSA-N 0.000 claims description 2
• VQPILDBFKHSXKZ-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-[3-(difluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=CC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)F)=O VQPILDBFKHSXKZ-UHFFFAOYSA-N 0.000 claims description 2
• ZOQKLKUOEXHOMB-UHFFFAOYSA-N 1-(cyclobutylmethyl)-6-(4-fluoro-3-methylphenyl)pyrrolo[3,2-b]pyridine 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.C1(CCC1)CN1C=CC2=NC=C(C=C21)C2=CC(=C(C=C2)F)C ZOQKLKUOEXHOMB-UHFFFAOYSA-N 0.000 claims description 2
• LLNDWQBNIZRFOB-UHFFFAOYSA-N 1-(cyclopropylmethyl)-6-(4-fluoro-3-methylphenyl)pyrrolo[3,2-b]pyridine 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.C1(CC1)CN1C=CC2=NC=C(C=C21)C2=CC(=C(C=C2)F)C LLNDWQBNIZRFOB-UHFFFAOYSA-N 0.000 claims description 2
• BSRWBJLTZLKFRD-UHFFFAOYSA-N 1-cyclobutyl-2-[6-(3-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound C1(CCC1)C(CN1C=CC2=NC=C(C=C21)C1=CC(=CC=C1)F)=O BSRWBJLTZLKFRD-UHFFFAOYSA-N 0.000 claims description 2
• IUPPUCRRHXFPFD-UHFFFAOYSA-N 1-cyclobutyl-2-[6-(4-fluoro-3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound C1(CCC1)C(CN1C=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C)=O IUPPUCRRHXFPFD-UHFFFAOYSA-N 0.000 claims description 2
• VYXJIACTCLDDJT-UHFFFAOYSA-N 1-cyclobutyl-2-[6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound C1(CCC1)C(CN1C=CC2=NC=C(C=C21)C1=CC=C(C=C1)F)=O VYXJIACTCLDDJT-UHFFFAOYSA-N 0.000 claims description 2
• COEWRDVSPRCJPD-UHFFFAOYSA-N 1-cyclopropyl-2-[3-fluoro-6-(3,4,5-trifluorophenyl)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)F)F)F)=O COEWRDVSPRCJPD-UHFFFAOYSA-N 0.000 claims description 2
• YKCSSZQLJYXKBF-UHFFFAOYSA-N 1-cyclopropyl-2-[3-fluoro-6-(4-fluorophenyl)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)F)=O YKCSSZQLJYXKBF-UHFFFAOYSA-N 0.000 claims description 2
• ILSYYKIDWBDSRH-UHFFFAOYSA-N 1-cyclopropyl-2-[3-fluoro-6-(4-methylthiophen-2-yl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound C1(CC1)C(CN1C=C(C2=NC=C(C=C21)C=1SC=C(C=1)C)F)=O ILSYYKIDWBDSRH-UHFFFAOYSA-N 0.000 claims description 2
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• DKKTXSJSIPANKY-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-chloro-6-(5-ethylthiophen-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)CC)Cl)=O DKKTXSJSIPANKY-UHFFFAOYSA-N 0.000 claims 1
• VWQQJLMDNMKDDM-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-chloro-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)Cl)=O VWQQJLMDNMKDDM-UHFFFAOYSA-N 0.000 claims 1
• NNULZSTZULXEBN-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-chloro-6-[3-(difluoromethyl)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)Cl)=O NNULZSTZULXEBN-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• QJNWRQXKIWRAOK-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-fluoro-2-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)F)C)=O QJNWRQXKIWRAOK-UHFFFAOYSA-N 0.000 claims 1
• WIXIXLKFGPPAPM-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-fluoro-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)F)=O WIXIXLKFGPPAPM-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
• 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
• NKQVNHJRWYIRHD-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-methyl-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)C)=O NKQVNHJRWYIRHD-UHFFFAOYSA-N 0.000 claims 1
• DEJFFVOEVUCGGT-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-methyl-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)C)=O DEJFFVOEVUCGGT-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
• VSEJIAHEJSBQGB-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-methyl-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)C)=O VSEJIAHEJSBQGB-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
• SSIKZPMJBAJYNA-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(2,3-difluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=CC2=NC=C(C=C21)C1=C(C(=CC=C1)F)F)=O SSIKZPMJBAJYNA-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
• JJONEJJNTYNARQ-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(2,4-difluorophenyl)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)=O JJONEJJNTYNARQ-UHFFFAOYSA-N 0.000 claims 1
• UYXOMWMPYRQPMZ-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(2,5-difluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=CC2=NC=C(C=C21)C1=C(C=CC(=C1)F)F)=O UYXOMWMPYRQPMZ-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
• MNJFWXUQJIOQKG-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(3,4-difluorophenyl)-3-fluoropyrrolo[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)=O MNJFWXUQJIOQKG-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
• REFCQYWYUQKNRR-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(3,4-difluorophenyl)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)=O REFCQYWYUQKNRR-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
• 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
• NJQPXRGCJFEHED-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(3-ethylphenyl)-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)CC)F)=O NJQPXRGCJFEHED-UHFFFAOYSA-N 0.000 claims 1
• RZZXEHCEGRZDEV-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(3-ethylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=CC2=NC=C(C=C21)C1=CC(=CC=C1)CC)=O RZZXEHCEGRZDEV-UHFFFAOYSA-N 0.000 claims 1
• CUVLJJXEWXNENH-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(3-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=CC2=NC=C(C=C21)C1=CC(=CC=C1)F)=O CUVLJJXEWXNENH-UHFFFAOYSA-N 0.000 claims 1
• DAUFBMVIIOKPFE-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(4-fluoro-3-methylphenyl)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)C)=O DAUFBMVIIOKPFE-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
• WCULXXDCQDIWLH-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(4-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=CC2=NC=C(C=C21)C1=CC=C(C=C1)C)=O WCULXXDCQDIWLH-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
• WJEONPPCMZEJBT-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(5-ethylthiophen-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)CC)F)=O WJEONPPCMZEJBT-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
• IGRZSMRBKPDTMU-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-[4-fluoro-3-(trifluoromethyl)phenyl]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)C(F)(F)F)=O IGRZSMRBKPDTMU-UHFFFAOYSA-N 0.000 claims 1
• GOOQJQFOTQTVQZ-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-[5-(trifluoromethyl)pyridin-3-yl]pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=CC2=NC=C(C=C21)C=1C=NC=C(C=1)C(F)(F)F)=O GOOQJQFOTQTVQZ-UHFFFAOYSA-N 0.000 claims 1
• QYTBFIOKRPUJOW-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-[6-(trifluoromethyl)pyridin-2-yl]pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=CC2=NC=C(C=C21)C1=NC(=CC=C1)C(F)(F)F)=O QYTBFIOKRPUJOW-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• YWBBNQRFXJOMMA-UHFFFAOYSA-N 1-[2-[6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]acetyl]azetidine-3-carbonitrile Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=1)C=CN2CC(=O)N1CC(C1)C#N YWBBNQRFXJOMMA-UHFFFAOYSA-N 0.000 claims 1
• IXBXEXJWTDZROH-UHFFFAOYSA-N 1-[3-fluoro-6-(3,4,5-trifluorophenyl)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)F)F)CC(C(C)C)=O IXBXEXJWTDZROH-UHFFFAOYSA-N 0.000 claims 1
• QCZVEAJGIWVOKA-UHFFFAOYSA-N 1-[3-fluoro-6-(3,4,5-trifluorophenyl)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)F)F)CC(CC)=O QCZVEAJGIWVOKA-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• IZUICHIJLGXBSD-UHFFFAOYSA-N 1-[3-fluoro-6-(4-fluorophenyl)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)CC(C(C)C)=O IZUICHIJLGXBSD-UHFFFAOYSA-N 0.000 claims 1
• VESZHPBOHOGHOK-UHFFFAOYSA-N 1-[3-fluoro-6-(4-methylthiophen-2-yl)pyrrolo[3,2-b]pyridin-1-yl]-3-methylbutan-2-one Chemical compound FC1=CN(C=2C1=NC=C(C=2)C=1SC=C(C=1)C)CC(C(C)C)=O VESZHPBOHOGHOK-UHFFFAOYSA-N 0.000 claims 1
• AUDZYNIXCICHFM-UHFFFAOYSA-N 1-[3-fluoro-6-(4-methylthiophen-2-yl)pyrrolo[3,2-b]pyridin-1-yl]butan-2-one Chemical compound FC1=CN(C=2C1=NC=C(C=2)C=1SC=C(C=1)C)CC(CC)=O AUDZYNIXCICHFM-UHFFFAOYSA-N 0.000 claims 1
• RETIMMANBJCYIS-UHFFFAOYSA-N 1-[3-fluoro-6-[3-(trifluoromethyl)phenyl]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)C(F)(F)F)CC(C(C)C)=O RETIMMANBJCYIS-UHFFFAOYSA-N 0.000 claims 1
• AEBWOEPBNLQRMQ-UHFFFAOYSA-N 1-[6-(2,3-dimethylphenyl)pyrrolo[3,2-b]pyridin-1-yl]-3-methylbutan-2-one Chemical compound CC1=C(C=CC=C1C)C=1C=C2C(=NC=1)C=CN2CC(C(C)C)=O AEBWOEPBNLQRMQ-UHFFFAOYSA-N 0.000 claims 1
• NPOLXECGCQTCED-UHFFFAOYSA-N 1-[6-[3-(difluoromethyl)phenyl]-3-fluoropyrrolo[3,2-b]pyridin-1-yl]-3-methylbutan-2-one Chemical compound FC(C=1C=C(C=CC=1)C=1C=C2C(=NC=1)C(=CN2CC(C(C)C)=O)F)F NPOLXECGCQTCED-UHFFFAOYSA-N 0.000 claims 1
• WRIRWGXAZZRASO-UHFFFAOYSA-N 1-[6-[3-(difluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1-yl]-3,3-dimethylbutan-2-one Chemical compound FC(C=1C=C(C=CC=1)C=1C=C2C(=NC=1)C=CN2CC(C(C)(C)C)=O)F WRIRWGXAZZRASO-UHFFFAOYSA-N 0.000 claims 1
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