JP2018520170A5 - - Google Patents

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Publication number

JP2018520170A5

JP2018520170A5 JP2018500737A JP2018500737A JP2018520170A5 JP 2018520170 A5 JP2018520170 A5 JP 2018520170A5 JP 2018500737 A JP2018500737 A JP 2018500737A JP 2018500737 A JP2018500737 A JP 2018500737A JP 2018520170 A5 JP2018520170 A5 JP 2018520170A5

Authority

JP

Japan

Prior art keywords

pyrrolo

pyridin

ethanone

methyl

fluoro

Prior art date

2016-07-07

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.)

Granted

Links

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• -1 3-azabicyclo [3.1.0] hexan-3-yl Chemical group 0.000 claims description 156
• 125000000217 alkyl group Chemical group 0.000 claims description 76
• 125000005843 halogen group Chemical group 0.000 claims description 64
• 150000001875 compounds Chemical class 0.000 claims description 52
• 125000001188 haloalkyl group Chemical group 0.000 claims description 50
• 150000003839 salts Chemical class 0.000 claims description 39
• 239000012453 solvate Substances 0.000 claims description 38
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 31
• 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 30
• 150000001204 N-oxides Chemical class 0.000 claims description 26
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 26
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 22
• 208000035475 disorder Diseases 0.000 claims description 17
• 125000001544 thienyl group Chemical group 0.000 claims description 17
• 125000003545 alkoxy group Chemical group 0.000 claims description 16
• 201000010099 disease Diseases 0.000 claims description 13
• 125000004076 pyridyl group Chemical group 0.000 claims description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 10
• 230000001404 mediated effect Effects 0.000 claims description 10
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 9
• 108010038912 Retinoid X Receptors Proteins 0.000 claims description 8
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 8
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 8
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
• 208000026106 cerebrovascular disease Diseases 0.000 claims description 8
• 230000000694 effects Effects 0.000 claims description 8
• 238000000034 method Methods 0.000 claims description 8
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 206010015037 epilepsy Diseases 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 4
• 208000012902 Nervous system disease Diseases 0.000 claims description 4
• 208000002193 Pain Diseases 0.000 claims description 4
• 208000027520 Somatoform disease Diseases 0.000 claims description 4
• 208000028552 Treatment-Resistant Depressive disease Diseases 0.000 claims description 4
• 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 4
• 125000002393 azetidinyl group Chemical group 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 4
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• 208000024714 major depressive disease Diseases 0.000 claims description 4
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
• 230000000926 neurological effect Effects 0.000 claims description 4
• 125000002971 oxazolyl group Chemical group 0.000 claims description 4
• 125000003566 oxetanyl group Chemical group 0.000 claims description 4
• 125000000466 oxiranyl group Chemical group 0.000 claims description 4
• 125000003386 piperidinyl group Chemical group 0.000 claims description 4
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• QGKLPGKXAVVPOJ-UHFFFAOYSA-N pyrrolidin-3-one Chemical compound O=C1CCNC1 QGKLPGKXAVVPOJ-UHFFFAOYSA-N 0.000 claims description 4
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
• 125000000335 thiazolyl group Chemical group 0.000 claims description 4
• FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims description 3
• 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 claims description 3
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 3
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
• DCPBVEYVXTZNEJ-UHFFFAOYSA-N 1-(2,2-dimethylmorpholin-4-yl)-2-[6-(4-fluoro-3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.CC1(CN(CCO1)C(CN1C=CC2=NC=C(C=C21)C2=CC(=C(C=C2)F)C)=O)C DCPBVEYVXTZNEJ-UHFFFAOYSA-N 0.000 claims description 2
• PKZJNWXWVVQEFU-UHFFFAOYSA-N 1-(2,2-dimethylpyrrolidin-1-yl)-2-[6-(4-fluoro-3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.CC1(N(CCC1)C(CN1C=CC2=NC=C(C=C21)C2=CC(=C(C=C2)F)C)=O)C PKZJNWXWVVQEFU-UHFFFAOYSA-N 0.000 claims description 2
• CMNRQPGGPJMOGZ-UHFFFAOYSA-N 1-(3,3-difluoroazetidin-1-yl)-2-(3-methyl-6-phenylpyrrolo[3,2-b]pyridin-1-yl)ethanone Chemical compound FC1(CN(C1)C(CN1C=C(C2=NC=C(C=C21)C1=CC=CC=C1)C)=O)F CMNRQPGGPJMOGZ-UHFFFAOYSA-N 0.000 claims description 2
• CQRSDPAZLOMIRL-UHFFFAOYSA-N 1-(3,3-difluoroazetidin-1-yl)-2-[3-methyl-6-(2,3,4-trifluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1(CN(C1)C(CN1C=C(C2=NC=C(C=C21)C1=C(C(=C(C=C1)F)F)F)C)=O)F CQRSDPAZLOMIRL-UHFFFAOYSA-N 0.000 claims description 2
• MUJRUDODDGFWKK-UHFFFAOYSA-N 1-(3,3-difluoroazetidin-1-yl)-2-[3-methyl-6-(5-methylthiophen-2-yl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1(CN(C1)C(CN1C=C(C2=NC=C(C=C21)C=1SC(=CC=1)C)C)=O)F MUJRUDODDGFWKK-UHFFFAOYSA-N 0.000 claims description 2
• BGUXDQINFLODFI-UHFFFAOYSA-N 1-(3,3-difluoroazetidin-1-yl)-2-[3-methyl-6-[3-(trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1(CN(C1)C(CN1C=C(C2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)C)=O)F BGUXDQINFLODFI-UHFFFAOYSA-N 0.000 claims description 2
• UBGLTLOEHIVLML-UHFFFAOYSA-N 1-(3,3-difluoroazetidin-1-yl)-2-[6-(2-fluoro-3-methylphenyl)-3-methylpyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1(CN(C1)C(CN1C=C(C2=NC=C(C=C21)C1=C(C(=CC=C1)C)F)C)=O)F UBGLTLOEHIVLML-UHFFFAOYSA-N 0.000 claims description 2
• PBWKVBBVCJCVPC-UHFFFAOYSA-N 1-(3,3-difluoroazetidin-1-yl)-2-[6-(2-fluorophenyl)-3-methylpyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1(CN(C1)C(CN1C=C(C2=NC=C(C=C21)C1=C(C=CC=C1)F)C)=O)F PBWKVBBVCJCVPC-UHFFFAOYSA-N 0.000 claims description 2
• YGPPKMMFUIUIKA-UHFFFAOYSA-N 1-(3,3-difluoroazetidin-1-yl)-2-[6-(3,4,5-trifluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1(CN(C1)C(CN1C=CC2=NC=C(C=C21)C1=CC(=C(C(=C1)F)F)F)=O)F YGPPKMMFUIUIKA-UHFFFAOYSA-N 0.000 claims description 2
• AQQBWBWFYLOFKU-UHFFFAOYSA-N 1-(3,3-difluoroazetidin-1-yl)-2-[6-(3,4-difluorophenyl)-3-methylpyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1(CN(C1)C(CN1C=C(C2=NC=C(C=C21)C1=CC(=C(C=C1)F)F)C)=O)F AQQBWBWFYLOFKU-UHFFFAOYSA-N 0.000 claims description 2
• HJYZEQRCJLUDGQ-UHFFFAOYSA-N 1-(3,3-difluoroazetidin-1-yl)-2-[6-(3,4-difluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1(CN(C1)C(CN1C=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)F)=O)F HJYZEQRCJLUDGQ-UHFFFAOYSA-N 0.000 claims description 2
• BJJKDBZTSJAUDR-UHFFFAOYSA-N 1-(3,3-difluoroazetidin-1-yl)-2-[6-(3,5-difluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1(CN(C1)C(CN1C=CC2=NC=C(C=C21)C1=CC(=CC(=C1)F)F)=O)F BJJKDBZTSJAUDR-UHFFFAOYSA-N 0.000 claims description 2
• VFKJSDMHSMUVIZ-UHFFFAOYSA-N 1-(3,3-difluoroazetidin-1-yl)-2-[6-(3-ethylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.FC1(CN(C1)C(CN1C=CC2=NC=C(C=C21)C2=CC(=CC=C2)CC)=O)F VFKJSDMHSMUVIZ-UHFFFAOYSA-N 0.000 claims description 2
• AZXMMNRKJQHWTQ-UHFFFAOYSA-N 1-(3,3-difluoroazetidin-1-yl)-2-[6-(3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1(CN(C1)C(CN1C=CC2=NC=C(C=C21)C=1C=C(C=CC=1)C)=O)F AZXMMNRKJQHWTQ-UHFFFAOYSA-N 0.000 claims description 2
• DKMPPDOTEKTSAO-UHFFFAOYSA-N 1-(3,3-difluoroazetidin-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.FC1(CN(C1)C(CN1C=CC2=NC=C(C=C21)C2=C(C=C(C=C2)F)C)=O)F DKMPPDOTEKTSAO-UHFFFAOYSA-N 0.000 claims description 2
• WEUPNUGVXQAOBV-UHFFFAOYSA-N 1-(3,3-difluoroazetidin-1-yl)-2-[6-(4-fluoro-3-methylphenyl)-3-methylpyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1(CN(C1)C(CN1C=C(C2=NC=C(C=C21)C1=CC(=C(C=C1)F)C)C)=O)F WEUPNUGVXQAOBV-UHFFFAOYSA-N 0.000 claims description 2
• LTNGUKKQBIBDFG-UHFFFAOYSA-N 1-(3,3-difluoroazetidin-1-yl)-2-[6-(4-fluoro-3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.FC1(CN(C1)C(CN1C=CC2=NC=C(C=C21)C2=CC(=C(C=C2)F)C)=O)F LTNGUKKQBIBDFG-UHFFFAOYSA-N 0.000 claims description 2
• BSEZSCVASXCHDZ-UHFFFAOYSA-N 1-(3,3-difluoroazetidin-1-yl)-2-[6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1(CN(C1)C(CN1C=CC2=NC=C(C=C21)C1=CC=C(C=C1)F)=O)F BSEZSCVASXCHDZ-UHFFFAOYSA-N 0.000 claims description 2
• GSMMLKDMNBANQU-UHFFFAOYSA-N 1-(3,3-difluoroazetidin-1-yl)-2-[6-(4-methylthiophen-2-yl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1(CN(C1)C(CN1C=CC2=NC=C(C=C21)C=1SC=C(C=1)C)=O)F GSMMLKDMNBANQU-UHFFFAOYSA-N 0.000 claims description 2
• PKUGPBCEVLNXHD-UHFFFAOYSA-N 1-(3,3-difluoroazetidin-1-yl)-2-[6-(5-ethylthiophen-2-yl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1(CN(C1)C(CN1C=CC2=NC=C(C=C21)C=1SC(=CC=1)CC)=O)F PKUGPBCEVLNXHD-UHFFFAOYSA-N 0.000 claims description 2
• VBZBRBPLXUIBHY-UHFFFAOYSA-N 1-(3,3-difluoroazetidin-1-yl)-2-[6-(5-methylthiophen-2-yl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1(CN(C1)C(CN1C=CC2=NC=C(C=C21)C=1SC(=CC=1)C)=O)F VBZBRBPLXUIBHY-UHFFFAOYSA-N 0.000 claims description 2
• KKVQLZYWHUHLFH-UHFFFAOYSA-N 1-(3,3-difluoroazetidin-1-yl)-2-[6-[4-fluoro-3-(trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1(CN(C1)C(CN1C=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C(F)(F)F)=O)F KKVQLZYWHUHLFH-UHFFFAOYSA-N 0.000 claims description 2
• MPKCFBHRFRMHGV-UHFFFAOYSA-N 1-(3,3-difluoroazetidin-1-yl)-2-[6-[6-(trifluoromethyl)pyridin-2-yl]pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1(CN(C1)C(CN1C=CC2=NC=C(C=C21)C1=NC(=CC=C1)C(F)(F)F)=O)F MPKCFBHRFRMHGV-UHFFFAOYSA-N 0.000 claims description 2
• ZVVBCUSNXGXCEG-UHFFFAOYSA-N 1-(3,3-difluoropyrrolidin-1-yl)-2-[6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1(CN(CC1)C(CN1C=CC2=NC=C(C=C21)C1=CC=C(C=C1)F)=O)F ZVVBCUSNXGXCEG-UHFFFAOYSA-N 0.000 claims description 2
• TVCJIMSDKOKGBQ-UHFFFAOYSA-N 1-(3,3-dimethylazetidin-1-yl)-2-[6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound CC1(CN(C1)C(CN1C=CC2=NC=C(C=C21)C1=CC=C(C=C1)F)=O)C TVCJIMSDKOKGBQ-UHFFFAOYSA-N 0.000 claims description 2
• LYEXXUNMTISGPU-UHFFFAOYSA-N 1-(3-fluoroazetidin-1-yl)-2-(3-fluoro-6-phenylpyrrolo[3,2-b]pyridin-1-yl)ethanone Chemical compound FC1CN(C1)C(CN1C=C(C2=NC=C(C=C21)C1=CC=CC=C1)F)=O LYEXXUNMTISGPU-UHFFFAOYSA-N 0.000 claims description 2
• XZYQNWDQUPAZSK-UHFFFAOYSA-N 1-(3-fluoroazetidin-1-yl)-2-(3-methyl-6-phenylpyrrolo[3,2-b]pyridin-1-yl)ethanone Chemical compound FC1CN(C1)C(CN1C=C(C2=NC=C(C=C21)C1=CC=CC=C1)C)=O XZYQNWDQUPAZSK-UHFFFAOYSA-N 0.000 claims description 2
• RDFMUAWCPGKYAV-UHFFFAOYSA-N 1-(3-fluoroazetidin-1-yl)-2-(6-phenylpyrrolo[3,2-b]pyridin-1-yl)ethanone Chemical compound FC1CN(C1)C(CN1C=CC2=NC=C(C=C21)C1=CC=CC=C1)=O RDFMUAWCPGKYAV-UHFFFAOYSA-N 0.000 claims description 2
• 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
• YDCUFXYAQJDIKV-UHFFFAOYSA-N 1-(3-fluoroazetidin-1-yl)-2-[3-fluoro-6-(2,3,4-trifluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1CN(C1)C(CN1C=C(C2=NC=C(C=C21)C1=C(C(=C(C=C1)F)F)F)F)=O YDCUFXYAQJDIKV-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• JPDNXDCYHCBLFD-UHFFFAOYSA-N 1-(3-fluoroazetidin-1-yl)-2-[3-fluoro-6-(2-fluorophenyl)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)F)F)=O JPDNXDCYHCBLFD-UHFFFAOYSA-N 0.000 claims description 2
• ADIYNWKRGQNXOO-UHFFFAOYSA-N 1-(3-fluoroazetidin-1-yl)-2-[3-fluoro-6-(3,4,5-trifluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1CN(C1)C(CN1C=C(C2=NC=C(C=C21)C1=CC(=C(C(=C1)F)F)F)F)=O ADIYNWKRGQNXOO-UHFFFAOYSA-N 0.000 claims description 2
• VPCYAHHOKUCVPM-UHFFFAOYSA-N 1-(3-fluoroazetidin-1-yl)-2-[3-fluoro-6-(3-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1CN(C1)C(CN1C=C(C2=NC=C(C=C21)C1=CC(=CC=C1)F)F)=O VPCYAHHOKUCVPM-UHFFFAOYSA-N 0.000 claims description 2
• AYENDJLOFDGTHU-UHFFFAOYSA-N 1-(3-fluoroazetidin-1-yl)-2-[3-fluoro-6-(3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1CN(C1)C(CN1C=C(C2=NC=C(C=C21)C=1C=C(C=CC=1)C)F)=O AYENDJLOFDGTHU-UHFFFAOYSA-N 0.000 claims description 2
• ZMGLZGZOOCMGEJ-UHFFFAOYSA-N 1-(3-fluoroazetidin-1-yl)-2-[3-fluoro-6-(4-fluoro-3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1CN(C1)C(CN1C=C(C2=NC=C(C=C21)C1=CC(=C(C=C1)F)C)F)=O ZMGLZGZOOCMGEJ-UHFFFAOYSA-N 0.000 claims description 2
• XHPKSXUNSNVDEI-UHFFFAOYSA-N 1-(3-fluoroazetidin-1-yl)-2-[3-fluoro-6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1CN(C1)C(CN1C=C(C2=NC=C(C=C21)C1=CC=C(C=C1)F)F)=O XHPKSXUNSNVDEI-UHFFFAOYSA-N 0.000 claims description 2
• AOVTWZGWBFGFMZ-UHFFFAOYSA-N 1-(3-fluoroazetidin-1-yl)-2-[3-fluoro-6-(4-methylthiophen-2-yl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1CN(C1)C(CN1C=C(C2=NC=C(C=C21)C=1SC=C(C=1)C)F)=O AOVTWZGWBFGFMZ-UHFFFAOYSA-N 0.000 claims description 2
• AWBWNWSOGLTKOF-UHFFFAOYSA-N 1-(3-fluoroazetidin-1-yl)-2-[3-fluoro-6-[2-fluoro-3-(trifluoromethyl)phenyl]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)F)F)F)=O AWBWNWSOGLTKOF-UHFFFAOYSA-N 0.000 claims description 2
• DPZTVNFZBXUOHX-UHFFFAOYSA-N 1-(3-fluoroazetidin-1-yl)-2-[3-fluoro-6-[3-(trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1CN(C1)C(CN1C=C(C2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)F)=O DPZTVNFZBXUOHX-UHFFFAOYSA-N 0.000 claims description 2
• VXOAEPYUOOYTKE-UHFFFAOYSA-N 1-(3-fluoroazetidin-1-yl)-2-[3-fluoro-6-[4-fluoro-3-(trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1CN(C1)C(CN1C=C(C2=NC=C(C=C21)C1=CC(=C(C=C1)F)C(F)(F)F)F)=O VXOAEPYUOOYTKE-UHFFFAOYSA-N 0.000 claims description 2
• ANOWTTPTSYCZOA-UHFFFAOYSA-N 1-(3-fluoroazetidin-1-yl)-2-[3-methyl-6-(2,3,4-trifluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1CN(C1)C(CN1C=C(C2=NC=C(C=C21)C1=C(C(=C(C=C1)F)F)F)C)=O ANOWTTPTSYCZOA-UHFFFAOYSA-N 0.000 claims description 2
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• 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 description 2
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• PMNZKYBCYXDRKO-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-chloro-6-[5-(trifluoromethyl)pyridin-3-yl]pyrrolo[3,2-b]pyridin-1-yl]ethanone 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC(F)(F)c1cncc(c1)-c1cnc2c(Cl)cn(CC(=O)N3CCC3)c2c1 PMNZKYBCYXDRKO-UHFFFAOYSA-N 0.000 claims description 2
• NHZNCICGAROOPP-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-chloro-6-[6-(trifluoromethyl)pyridin-2-yl]pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound N1(CCC1)C(CN1C=C(C2=NC=C(C=C21)C1=NC(=CC=C1)C(F)(F)F)Cl)=O NHZNCICGAROOPP-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• LCUVIKDMHWKRAU-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-fluoro-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)F)=O LCUVIKDMHWKRAU-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
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• TUJKUJMVVRPGEU-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-fluoro-6-[2-fluoro-3-(trifluoromethyl)phenyl]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)(F)F)F)F)=O TUJKUJMVVRPGEU-UHFFFAOYSA-N 0.000 claims description 2
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• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• JRBCFPFQISNNJA-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(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=CS1)=O JRBCFPFQISNNJA-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
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• FFGVQKZODWNRJH-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(2,4-difluoro-3-methylphenyl)-3-methylpyrrolo[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)C)=O FFGVQKZODWNRJH-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
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• 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 description 2
• RQRZOYDXCOXSQB-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(2-fluoro-3-methylphenyl)-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)C)F)C)=O RQRZOYDXCOXSQB-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
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• 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
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• 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 description 2
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• 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 description 2
• WNPWTKLGTMIMGU-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[6-(3-chloro-4-fluorophenyl)-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)Cl)F)=O WNPWTKLGTMIMGU-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
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• 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 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
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
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