JP7219223B2 - ＬＲＲＫ２阻害剤としての新規のイミダゾ［４，５－ｃ］キノリン誘導体 - Google Patents

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Publication number

JP7219223B2

JP7219223B2 JP2019549462A JP2019549462A JP7219223B2 JP 7219223 B2 JP7219223 B2 JP 7219223B2 JP 2019549462 A JP2019549462 A JP 2019549462A JP 2019549462 A JP2019549462 A JP 2019549462A JP 7219223 B2 JP7219223 B2 JP 7219223B2

Authority

JP

Japan

Prior art keywords

methyl

imidazo

quinoline

chloro

pyran

Prior art date

2017-03-10

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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• ITIRVXDSMXFTPW-UHFFFAOYSA-N 1H-imidazo[4,5-c]quinoline Chemical class C1=CC=CC2=C(NC=N3)C3=CN=C21 ITIRVXDSMXFTPW-UHFFFAOYSA-N 0.000 title description 7
• 229940124786 LRRK2 inhibitor Drugs 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims description 247
• -1 2,2-difluoropropyl Chemical group 0.000 claims description 89
• 150000003839 salts Chemical class 0.000 claims description 79
• 125000004429 atom Chemical group 0.000 claims description 49
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 42
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
• 208000018737 Parkinson disease Diseases 0.000 claims description 27
• 208000024827 Alzheimer disease Diseases 0.000 claims description 22
• 208000011231 Crohn disease Diseases 0.000 claims description 21
• 201000010099 disease Diseases 0.000 claims description 21
• 208000035475 disorder Diseases 0.000 claims description 20
• 239000008194 pharmaceutical composition Substances 0.000 claims description 14
• 206010012289 Dementia Diseases 0.000 claims description 13
• VDSACXZRWKTZKA-UHFFFAOYSA-N 8-chloro-1-(3,3-difluorooxan-4-yl)-2-[(5-methylpyrazin-2-yl)methyl]imidazo[4,5-c]quinoline Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3C1C(COCC1)(F)F)CC1=NC=C(N=C1)C VDSACXZRWKTZKA-UHFFFAOYSA-N 0.000 claims description 11
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
• GKXUIOCXHLDEQL-HOTGVXAUSA-N 2-[(2R,4S)-4-(8-chloro-2-cyclobutylimidazo[4,5-c]quinolin-1-yl)oxan-2-yl]acetonitrile Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3[C@@H]1C[C@@H](OCC1)CC#N)C1CCC1 GKXUIOCXHLDEQL-HOTGVXAUSA-N 0.000 claims description 10
• KIMFZTFAVICDGC-UHFFFAOYSA-N 8-chloro-1-(4,4-difluoro-1-methylpyrrolidin-3-yl)-2-(1,2,4-triazol-1-ylmethyl)imidazo[4,5-c]quinoline Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3C1CN(CC1(F)F)C)CN1N=CN=C1 KIMFZTFAVICDGC-UHFFFAOYSA-N 0.000 claims description 10
• WYJBFPHJIUFSJH-UHFFFAOYSA-N 8-chloro-1-(4,4-difluoro-1-methylpyrrolidin-3-yl)-2-[[4-(methoxymethyl)triazol-1-yl]methyl]imidazo[4,5-c]quinoline Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3C1CN(CC1(F)F)C)CN1N=NC(=C1)COC WYJBFPHJIUFSJH-UHFFFAOYSA-N 0.000 claims description 10
• JJHOHPOGCOEIHB-ZIAGYGMSSA-N 2-[(2S,4R)-4-(8-chloro-2-ethylimidazo[4,5-c]quinolin-1-yl)oxan-2-yl]acetonitrile Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3[C@H]1C[C@H](OCC1)CC#N)CC JJHOHPOGCOEIHB-ZIAGYGMSSA-N 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• SXIUZTAWZDYLBB-UHFFFAOYSA-N 1-(4,4-difluoro-1-methylpyrrolidin-3-yl)-2-[(4-methyltriazol-2-yl)methyl]imidazo[4,5-c]quinoline-8-carbonitrile Chemical compound FC1(C(CN(C1)C)N1C(=NC=2C=NC=3C=CC(=CC=3C=21)C#N)CN1N=CC(=N1)C)F SXIUZTAWZDYLBB-UHFFFAOYSA-N 0.000 claims description 8
• YDUTZRUUPJSWMS-KRWDZBQOSA-N 3-[[8-chloro-1-[(4S)-3,3-difluorooxan-4-yl]imidazo[4,5-c]quinolin-2-yl]methyl]-5-methyl-1,2-oxazole Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3[C@@H]1C(COCC1)(F)F)CC1=NOC(=C1)C YDUTZRUUPJSWMS-KRWDZBQOSA-N 0.000 claims description 8
• JWHNZKQHRKBAGP-UHFFFAOYSA-N 1-(4,4-difluoro-1-methylpyrrolidin-3-yl)-8-fluoro-2-[(5-methylpyrazin-2-yl)methyl]imidazo[4,5-c]quinoline Chemical compound FC1(C(CN(C1)C)N1C(=NC=2C=NC=3C=CC(=CC=3C=21)F)CC1=NC=C(N=C1)C)F JWHNZKQHRKBAGP-UHFFFAOYSA-N 0.000 claims description 7
• AJDNMIPYMHZCKI-IUODEOHRSA-N 1-[(2R,4R)-2-methyloxan-4-yl]-2-[(1-methyltriazol-4-yl)methyl]-8-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C[C@H]1OCC[C@H](C1)N1C(=NC=2C=NC=3C=CC(=CC=3C=21)C(F)(F)F)CC=1N=NN(C=1)C AJDNMIPYMHZCKI-IUODEOHRSA-N 0.000 claims description 7
• CBRMMIOJKMMQMI-RHSMWYFYSA-N 8-(difluoromethyl)-1-[(2R,4R)-2-methyloxan-4-yl]-2-[(5-methylpyrazin-2-yl)methyl]imidazo[4,5-c]quinoline Chemical compound FC(C1=CC=2C3=C(C=NC=2C=C1)N=C(N3[C@H]1C[C@H](OCC1)C)CC1=NC=C(N=C1)C)F CBRMMIOJKMMQMI-RHSMWYFYSA-N 0.000 claims description 7
• NHIUYAPDFWHHHY-UKRRQHHQSA-N 8-(difluoromethyl)-2-[(4-methoxypyrazol-1-yl)methyl]-1-[(2R,4R)-2-methyloxan-4-yl]imidazo[4,5-c]quinoline Chemical compound FC(C1=CC=2C3=C(C=NC=2C=C1)N=C(N3[C@H]1C[C@H](OCC1)C)CN1N=CC(=C1)OC)F NHIUYAPDFWHHHY-UKRRQHHQSA-N 0.000 claims description 7
• NJVPFRKLPUCXFR-ZRNDULBVSA-N [8-chloro-1-[(2R,4R)-2-methyloxan-4-yl]imidazo[4,5-c]quinolin-2-yl]-(5-methylpyrazin-2-yl)methanol Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3[C@H]1C[C@H](OCC1)C)C(O)C1=NC=C(N=C1)C NJVPFRKLPUCXFR-ZRNDULBVSA-N 0.000 claims description 7
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
• NZGUBUFNKSWTBS-QGZVFWFLSA-N 2-[(6-methylpyrimidin-4-yl)methyl]-1-[(3R)-1-methylpyrrolidin-3-yl]imidazo[4,5-c]quinoline-8-carbonitrile Chemical compound CC1=CC(=NC=N1)CC=1N(C2=C(C=NC=3C=CC(=CC2=3)C#N)N=1)[C@H]1CN(CC1)C NZGUBUFNKSWTBS-QGZVFWFLSA-N 0.000 claims description 6
• 206010024229 Leprosy Diseases 0.000 claims description 6
• 208000009829 Lewy Body Disease Diseases 0.000 claims description 6
• 201000002832 Lewy body dementia Diseases 0.000 claims description 6
• HSTKJGNVNYHXRI-CXAGYDPISA-N [5-[[8-fluoro-1-[(2R,4R)-2-methyloxan-4-yl]imidazo[4,5-c]quinolin-2-yl]methyl]pyrazin-2-yl]methanol Chemical compound C[C@H](C1)OCC[C@H]1N1C(C2=CC(F)=CC=C2N=C2)=C2N=C1CC1=CN=C(CO)C=N1 HSTKJGNVNYHXRI-CXAGYDPISA-N 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• CQCUMBBPDPDNLF-UHFFFAOYSA-N 1-(4,4-difluoro-1-methylpyrrolidin-3-yl)-8-fluoro-2-(1,2,4-triazol-1-ylmethyl)imidazo[4,5-c]quinoline Chemical compound FC1(C(CN(C1)C)N1C(=NC=2C=NC=3C=CC(=CC=3C=21)F)CN1N=CN=C1)F CQCUMBBPDPDNLF-UHFFFAOYSA-N 0.000 claims description 5
• FVNAQFOFKZUYGE-UHFFFAOYSA-N 1-(4,4-difluoro-1-methylpyrrolidin-3-yl)-8-fluoro-2-[(4-methyltriazol-1-yl)methyl]imidazo[4,5-c]quinoline Chemical compound FC1(C(CN(C1)C)N1C(=NC=2C=NC=3C=CC(=CC=3C=21)F)CN1N=NC(=C1)C)F FVNAQFOFKZUYGE-UHFFFAOYSA-N 0.000 claims description 5
• JJHOHPOGCOEIHB-KBPBESRZSA-N 2-[(2R,4S)-4-(8-chloro-2-ethylimidazo[4,5-c]quinolin-1-yl)oxan-2-yl]acetonitrile Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3[C@@H]1C[C@@H](OCC1)CC#N)CC JJHOHPOGCOEIHB-KBPBESRZSA-N 0.000 claims description 5
• 201000011240 Frontotemporal dementia Diseases 0.000 claims description 5
• UEOIDXNOHZNZQY-UHFFFAOYSA-N 1-(4,4-difluoro-1-methylpyrrolidin-3-yl)-2-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]imidazo[4,5-c]quinoline-8-carbonitrile Chemical compound FC1(C(CN(C1)C)N1C(=NC=2C=NC=3C=CC(=CC=3C=21)C#N)CC1=NOC(=N1)C)F UEOIDXNOHZNZQY-UHFFFAOYSA-N 0.000 claims description 4
• YVFMOFCDPODUPW-UHFFFAOYSA-N 3-[[8-chloro-1-(4,4-difluoro-1-methylpyrrolidin-3-yl)imidazo[4,5-c]quinolin-2-yl]methyl]-5-methyl-1,2,4-oxadiazole Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3C1CN(CC1(F)F)C)CC1=NOC(=N1)C YVFMOFCDPODUPW-UHFFFAOYSA-N 0.000 claims description 4
• UDXAXCRORVOLCH-UHFFFAOYSA-N 3-[[8-chloro-1-(4,4-difluoro-1-methylpyrrolidin-3-yl)imidazo[4,5-c]quinolin-2-yl]methyl]-5-methyl-1,2-oxazole Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3C1CN(CC1(F)F)C)CC1=NOC(=C1)C UDXAXCRORVOLCH-UHFFFAOYSA-N 0.000 claims description 4
• KTBGJOHKUJURCT-UHFFFAOYSA-N 8-chloro-1-(3,3-difluorooxan-4-yl)-2-(1,2,4-triazol-1-ylmethyl)imidazo[4,5-c]quinoline Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3C1C(COCC1)(F)F)CN1N=CN=C1 KTBGJOHKUJURCT-UHFFFAOYSA-N 0.000 claims description 4
• HRDKCILPIGUZSW-UHFFFAOYSA-N 8-chloro-1-(3,3-difluorooxan-4-yl)-2-[(4-methoxypyrazol-1-yl)methyl]imidazo[4,5-c]quinoline Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3C1C(COCC1)(F)F)CN1N=CC(=C1)OC HRDKCILPIGUZSW-UHFFFAOYSA-N 0.000 claims description 4
• PZOOYRZEJBBJQG-UHFFFAOYSA-N 8-chloro-1-(4,4-difluoro-1-methylpyrrolidin-3-yl)-2-(tetrazol-1-ylmethyl)imidazo[4,5-c]quinoline Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3C1CN(CC1(F)F)C)CN1N=NN=C1 PZOOYRZEJBBJQG-UHFFFAOYSA-N 0.000 claims description 4
• DTYXHKYEGPKZBD-UHFFFAOYSA-N 8-chloro-1-(4,4-difluoro-1-methylpyrrolidin-3-yl)-2-[(4-methyltriazol-1-yl)methyl]imidazo[4,5-c]quinoline Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3C1CN(CC1(F)F)C)CN1N=NC(=C1)C DTYXHKYEGPKZBD-UHFFFAOYSA-N 0.000 claims description 4
• 208000032859 Synucleinopathies Diseases 0.000 claims description 4
• 201000002212 progressive supranuclear palsy Diseases 0.000 claims description 4
• CITRKOBJFDHRPV-RHSMWYFYSA-N 1-[(2R,4R)-2-methyloxan-4-yl]-2-[(5-methylpyrazin-2-yl)methyl]-8-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound CC=1N=CC(=NC=1)CC=1N(C2=C(C=NC=3C=CC(=CC2=3)C(F)(F)F)N=1)[C@H]1C[C@H](OCC1)C CITRKOBJFDHRPV-RHSMWYFYSA-N 0.000 claims description 3
• CXFQDUVAIHZTLN-CQSZACIVSA-N 1-[(3R)-1-methylpyrrolidin-3-yl]-2-[(5-methyl-1,3,4-thiadiazol-2-yl)methyl]imidazo[4,5-c]quinoline-8-carbonitrile Chemical compound CN1C[C@@H](CC1)N1C(=NC=2C=NC=3C=CC(=CC=3C=21)C#N)CC=1SC(=NN=1)C CXFQDUVAIHZTLN-CQSZACIVSA-N 0.000 claims description 3
• CVIKJUDYOSLROL-CQSZACIVSA-N 1-[(3R)-1-methylpyrrolidin-3-yl]-2-[(5-methyltetrazol-2-yl)methyl]imidazo[4,5-c]quinoline-8-carbonitrile Chemical compound CN1C[C@@H](CC1)N1C(=NC=2C=NC=3C=CC(=CC=3C=21)C#N)CN1N=C(N=N1)C CVIKJUDYOSLROL-CQSZACIVSA-N 0.000 claims description 3
• PQZGQUILUHPZHY-KBPBESRZSA-N 2-[(2R,4S)-4-(8-chloro-2-methylimidazo[4,5-c]quinolin-1-yl)oxan-2-yl]acetonitrile Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3[C@@H]1C[C@@H](OCC1)CC#N)C PQZGQUILUHPZHY-KBPBESRZSA-N 0.000 claims description 3
• FDRYHDAOQMSCEU-QGZVFWFLSA-N 2-[(5-methylpyrazin-2-yl)methyl]-1-[(3R)-1-methylpyrrolidin-3-yl]imidazo[4,5-c]quinoline-8-carbonitrile Chemical compound CC=1N=CC(=NC=1)CC=1N(C2=C(C=NC=3C=CC(=CC2=3)C#N)N=1)[C@H]1CN(CC1)C FDRYHDAOQMSCEU-QGZVFWFLSA-N 0.000 claims description 3
• WTOAYUFZFCMTRI-RHSMWYFYSA-N 2-cyclopentyl-1-[(2R,4R)-2-methyloxan-4-yl]imidazo[4,5-c]quinoline-8-carbonitrile Chemical compound C1(CCCC1)C=1N(C2=C(C=NC=3C=CC(=CC2=3)C#N)N=1)[C@H]1C[C@H](OCC1)C WTOAYUFZFCMTRI-RHSMWYFYSA-N 0.000 claims description 3
• WLCCPOUANYCQHN-JYRZLJSNSA-N 3-[8-chloro-1-[(2R,4R)-2-methyloxan-4-yl]imidazo[4,5-c]quinolin-2-yl]-2-methylpropanenitrile Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3[C@H]1C[C@H](OCC1)C)CC(C#N)C WLCCPOUANYCQHN-JYRZLJSNSA-N 0.000 claims description 3
• ZQACZSXJTKLCDC-TZMCWYRMSA-N 3-[8-chloro-1-[(2R,4R)-2-methyloxan-4-yl]imidazo[4,5-c]quinolin-2-yl]propanenitrile Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3[C@H]1C[C@H](OCC1)C)CCC#N ZQACZSXJTKLCDC-TZMCWYRMSA-N 0.000 claims description 3
• FSBLOKSQGJCUQX-MLGOLLRUSA-N 6-[[8-fluoro-1-[(2R,4R)-2-methyloxan-4-yl]imidazo[4,5-c]quinolin-2-yl]methyl]-2-methylimidazo[2,1-b][1,3,4]thiadiazole Chemical compound FC1=CC=2C3=C(C=NC=2C=C1)N=C(N3[C@H]1C[C@H](OCC1)C)CC=1N=C2SC(=NN2C=1)C FSBLOKSQGJCUQX-MLGOLLRUSA-N 0.000 claims description 3
• YYSUHJMDOKKANR-VEDWFQBFSA-N 8-chloro-1-[(2R,4R)-2-methyloxan-4-yl]-2-[[5-(trideuteriomethyl)pyrazin-2-yl]methyl]imidazo[4,5-c]quinoline Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3[C@H]1C[C@H](OCC1)C)CC1=NC=C(N=C1)C([2H])([2H])[2H] YYSUHJMDOKKANR-VEDWFQBFSA-N 0.000 claims description 3
• FVVSTEPFOKNPBB-NCZHRSJASA-N ClC1=CC=2C3=C(C=NC2C=C1)N=C(N3[C@H]3C[C@H](OCC3)C)CC=3N=CC(=NC3)C(O)([2H])[2H] Chemical compound ClC1=CC=2C3=C(C=NC2C=C1)N=C(N3[C@H]3C[C@H](OCC3)C)CC=3N=CC(=NC3)C(O)([2H])[2H] FVVSTEPFOKNPBB-NCZHRSJASA-N 0.000 claims description 3
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• 125000001153 fluoro group Chemical group F* 0.000 claims description 3
• CIIFKVFOVFJZDM-UHFFFAOYSA-N quinoline-8-carbonitrile Chemical compound C1=CN=C2C(C#N)=CC=CC2=C1 CIIFKVFOVFJZDM-UHFFFAOYSA-N 0.000 claims description 3
• ATAOFFIDVVYZBN-UHFFFAOYSA-N 1-(4,4-difluoro-1-methylpyrrolidin-3-yl)-8-fluoro-2-[[4-(methoxymethyl)triazol-1-yl]methyl]imidazo[4,5-c]quinoline Chemical compound FC1(C(CN(C1)C)N1C(=NC=2C=NC=3C=CC(=CC=3C=21)F)CN1N=NC(=C1)COC)F ATAOFFIDVVYZBN-UHFFFAOYSA-N 0.000 claims description 2
• KYJCVOSIHXUMPZ-GOEBONIOSA-N 1-[(1R,3S)-3-fluorocyclopentyl]-2-[(5-methyl-1,2-oxazol-3-yl)methyl]imidazo[4,5-c]quinoline-8-carbonitrile Chemical compound F[C@@H]1C[C@@H](CC1)N1C(=NC=2C=NC=3C=CC(=CC=3C=21)C#N)CC1=NOC(=C1)C KYJCVOSIHXUMPZ-GOEBONIOSA-N 0.000 claims description 2
• PYFVAVZYKLONHU-TZMCWYRMSA-N 1-[(2R,4R)-2-methyloxan-4-yl]-2-(1,2,4-triazol-1-ylmethyl)-8-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C[C@H]1OCC[C@H](C1)N1C(=NC=2C=NC=3C=CC(=CC3C21)C(F)(F)F)CN2N=CN=C2 PYFVAVZYKLONHU-TZMCWYRMSA-N 0.000 claims description 2
• DIXGZQBMRWELNZ-UKRRQHHQSA-N 1-[(2R,4R)-2-methyloxan-4-yl]-2-(1,3-thiazol-2-ylmethyl)imidazo[4,5-c]quinoline-8-carbonitrile Chemical compound C[C@H]1OCC[C@H](C1)N1C(=NC=2C=NC=3C=CC(=CC=3C=21)C#N)CC=1SC=CN=1 DIXGZQBMRWELNZ-UKRRQHHQSA-N 0.000 claims description 2
• LBNLEKLWYDFWQU-BXUZGUMPSA-N 1-[(2R,4R)-2-methyloxan-4-yl]-2-[(5-methyltetrazol-2-yl)methyl]-8-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C[C@H]1OCC[C@H](C1)N1C(=NC=2C=NC=3C=CC(=CC=3C=21)C(F)(F)F)CN1N=C(N=N1)C LBNLEKLWYDFWQU-BXUZGUMPSA-N 0.000 claims description 2
• SSMBIZVRZOOHFM-RHSMWYFYSA-N 1-[(2R,4R)-2-methyloxan-4-yl]-2-[(6-methylpyrimidin-4-yl)methyl]-8-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound CC1=CC(=NC=N1)CC=1N(C2=C(C=NC=3C=CC(=CC2=3)C(F)(F)F)N=1)[C@H]1C[C@H](OCC1)C SSMBIZVRZOOHFM-RHSMWYFYSA-N 0.000 claims description 2
• AGXYYXCIONRLQO-CZUORRHYSA-N 1-[(2R,4R)-2-methyloxan-4-yl]-2-[[5-(trifluoromethyl)pyrazin-2-yl]methyl]imidazo[4,5-c]quinoline-8-carbonitrile Chemical compound C[C@H]1OCC[C@H](C1)N1C(=NC=2C=NC=3C=CC(=CC=3C=21)C#N)CC1=NC=C(N=C1)C(F)(F)F AGXYYXCIONRLQO-CZUORRHYSA-N 0.000 claims description 2
• SREKPUHBFRKUNE-JKSUJKDBSA-N 2-(1,3-benzoxazol-2-ylmethyl)-1-[(1R,3S)-3-fluorocyclopentyl]imidazo[4,5-c]quinoline-8-carbonitrile Chemical compound C1=C(C#N)C=C2C=3N(C(=NC=3C=NC2=C1)CC1=NC2=C(O1)C=CC=C2)[C@H]1C[C@@H](F)CC1 SREKPUHBFRKUNE-JKSUJKDBSA-N 0.000 claims description 2
• RFQANWFWGCCBDV-OAHLLOKOSA-N 2-[(3-methyl-1,2-oxazol-5-yl)methyl]-1-[(3R)-1-methylpyrrolidin-3-yl]imidazo[4,5-c]quinoline-8-carbonitrile Chemical compound CC1=NOC(=C1)CC=1N(C2=C(C=NC=3C=CC(=CC2=3)C#N)N=1)[C@H]1CN(CC1)C RFQANWFWGCCBDV-OAHLLOKOSA-N 0.000 claims description 2
• RRPCZAZAUKRYQS-UKRRQHHQSA-N 2-[(4-methoxypyrazol-1-yl)methyl]-1-[(2R,4R)-2-methyloxan-4-yl]-8-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound COC=1C=NN(C=1)CC=1N(C2=C(C=NC=3C=CC(=CC2=3)C(F)(F)F)N=1)[C@H]1C[C@H](OCC1)C RRPCZAZAUKRYQS-UKRRQHHQSA-N 0.000 claims description 2
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