CA3056030A1 - Novel imidazo[4,5-c]quinoline derivatives as lrrk2 inhibitors - Google Patents

Info

Publication number

CA3056030A1

CA3056030A1 CA3056030A CA3056030A CA3056030A1 CA 3056030 A1 CA3056030 A1 CA 3056030A1 CA 3056030 A CA3056030 A CA 3056030A CA 3056030 A CA3056030 A CA 3056030A CA 3056030 A1 CA3056030 A1 CA 3056030A1

Authority

CA

Canada

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.)

Pending

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 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 abstract description 6
• 229940124786 LRRK2 inhibitor Drugs 0.000 title description 6
• 150000001875 compounds Chemical class 0.000 claims abstract description 238
• 150000003839 salts Chemical class 0.000 claims abstract description 59
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 45
• 208000018737 Parkinson disease Diseases 0.000 claims abstract description 29
• 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 24
• 201000010099 disease Diseases 0.000 claims abstract description 20
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
• 208000011231 Crohn disease Diseases 0.000 claims abstract description 11
• 206010024229 Leprosy Diseases 0.000 claims abstract description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 121
• -1 2,2-difluoropropyl Chemical group 0.000 claims description 102
• 238000000034 method Methods 0.000 claims description 89
• 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 71
• CIIFKVFOVFJZDM-UHFFFAOYSA-N quinoline-8-carbonitrile Chemical compound C1=CN=C2C(C#N)=CC=CC2=C1 CIIFKVFOVFJZDM-UHFFFAOYSA-N 0.000 claims description 26
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 22
• 208000035475 disorder Diseases 0.000 claims description 20
• 206010012289 Dementia Diseases 0.000 claims description 12
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 201000011240 Frontotemporal dementia Diseases 0.000 claims description 7
• 208000009829 Lewy Body Disease Diseases 0.000 claims description 7
• 201000002832 Lewy body dementia Diseases 0.000 claims description 7
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 6
• 201000002212 progressive supranuclear palsy Diseases 0.000 claims description 6
• 208000032859 Synucleinopathies Diseases 0.000 claims description 5
• 208000034799 Tauopathies Diseases 0.000 claims description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
• 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 4
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 4
• 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 2
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
• 125000001153 fluoro group Chemical group F* 0.000 claims description 2
• XRPDDDRNQJNHLQ-UHFFFAOYSA-N 2-ethyl-1h-pyrrole Chemical compound CCC1=CC=CN1 XRPDDDRNQJNHLQ-UHFFFAOYSA-N 0.000 claims 8
• 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 6
• 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 6
• 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 5
• 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 4
• 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 4
• 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 3
• 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 3
• 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 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• QYANNJBVADZUDN-UHFFFAOYSA-N 5-hydroxymethyl-2-methylpyrazine Natural products CC1=CN=C(CO)C=N1 QYANNJBVADZUDN-UHFFFAOYSA-N 0.000 claims 2
• 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 2
• 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 2
• 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 2
• 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 claims 2
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• DVYRQIFEQFMRCS-GDBMZVCRSA-N 2-[(4-methoxypyrazol-1-yl)methyl]-1-[(2R,4R)-2-methyloxan-4-yl]imidazo[4,5-c]quinoline-8-carbonitrile Chemical compound COC=1C=NN(C1)CC=1N(C2=C(C=NC=3C=CC(=CC23)C#N)N1)[C@H]1C[C@H](OCC1)C DVYRQIFEQFMRCS-GDBMZVCRSA-N 0.000 claims 1
• VKBQZVKBWYNNAD-OAHLLOKOSA-N 2-[(4-methoxypyrazol-1-yl)methyl]-1-[(3R)-1-methylpyrrolidin-3-yl]imidazo[4,5-c]quinoline-8-carbonitrile Chemical compound COC=1C=NN(C=1)CC=1N(C2=C(C=NC=3C=CC(=CC2=3)C#N)N=1)[C@H]1CN(CC1)C VKBQZVKBWYNNAD-OAHLLOKOSA-N 0.000 claims 1
• DIQWEXIWVFAHMH-CQSZACIVSA-N 2-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]-1-[(3R)-1-(2,2,2-trifluoroethyl)pyrrolidin-3-yl]imidazo[4,5-c]quinoline-8-carbonitrile Chemical compound Cc1nc(Cc2nc3cnc4ccc(cc4c3n2[C@@H]2CCN(CC(F)(F)F)C2)C#N)no1 DIQWEXIWVFAHMH-CQSZACIVSA-N 0.000 claims 1
• GSGVNUZARKZDHD-OAHLLOKOSA-N 2-[(5-methyl-1,3-oxazol-2-yl)methyl]-1-[(3R)-1-methylpyrrolidin-3-yl]imidazo[4,5-c]quinoline-8-carbonitrile Chemical compound CC1=CN=C(O1)CC=1N(C2=C(C=NC=3C=CC(=CC2=3)C#N)N=1)[C@H]1CN(CC1)C GSGVNUZARKZDHD-OAHLLOKOSA-N 0.000 claims 1
• PQZGQUILUHPZHY-UHFFFAOYSA-N 2-[4-(8-chloro-2-methylimidazo[4,5-c]quinolin-1-yl)oxan-2-yl]acetonitrile Chemical compound C1(Cl)=CC2=C3N(C(=NC3=CN=C2C=C1)C)C1CCOC(C1)CC#N PQZGQUILUHPZHY-UHFFFAOYSA-N 0.000 claims 1
• RCGGAUIZOACTAZ-UHFFFAOYSA-N 2-[[8-chloro-1-(3,3-difluorooxan-4-yl)imidazo[4,5-c]quinolin-2-yl]methyl]-5-methyl-1,3,4-thiadiazole Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3C1C(COCC1)(F)F)CC=1SC(=NN=1)C RCGGAUIZOACTAZ-UHFFFAOYSA-N 0.000 claims 1
• HDRPMBPBBIFQPM-UHFFFAOYSA-N 2-[[8-chloro-1-(4,4-difluoro-1-methylpyrrolidin-3-yl)imidazo[4,5-c]quinolin-2-yl]methyl]-5-methyl-1,3,4-thiadiazole Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3C1CN(CC1(F)F)C)CC=1SC(=NN=1)C HDRPMBPBBIFQPM-UHFFFAOYSA-N 0.000 claims 1
• HUMKEKKKLFSBGD-TZMCWYRMSA-N 2-[[8-chloro-1-[(2R,4R)-2-methyloxan-4-yl]imidazo[4,5-c]quinolin-2-yl]methyl]-1,3-thiazole Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3[C@H]1C[C@H](OCC1)C)CC=1SC=CN=1 HUMKEKKKLFSBGD-TZMCWYRMSA-N 0.000 claims 1
• XZPDNSLAJUCFOU-TZMCWYRMSA-N 2-[[8-fluoro-1-[(2R,4R)-2-methyloxan-4-yl]imidazo[4,5-c]quinolin-2-yl]methyl]-1,3-thiazole Chemical compound FC1=CC=2C3=C(C=NC=2C=C1)N=C(N3[C@H]1C[C@H](OCC1)C)CC=1SC=CN=1 XZPDNSLAJUCFOU-TZMCWYRMSA-N 0.000 claims 1
• 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 1
• ZMQFKDFYMNVLLO-BXUZGUMPSA-N 2-methyl-5-[[1-[(2R,4R)-2-methyloxan-4-yl]-8-(trifluoromethyl)imidazo[4,5-c]quinolin-2-yl]methyl]-1,3,4-oxadiazole Chemical compound CC1=NN=C(O1)CC=1N(C2=C(C=NC=3C=CC(=CC2=3)C(F)(F)F)N=1)[C@H]1C[C@H](OCC1)C ZMQFKDFYMNVLLO-BXUZGUMPSA-N 0.000 claims 1
• WIROEAKAQSKZGH-BXUZGUMPSA-N 2-methyl-5-[[1-[(2R,4R)-2-methyloxan-4-yl]-8-(trifluoromethyl)imidazo[4,5-c]quinolin-2-yl]methyl]-1,3,4-thiadiazole Chemical compound C[C@H]1OCC[C@H](C1)N1C(=NC=2C=NC=3C=CC(=CC=3C=21)C(F)(F)F)CC=1SC(=NN=1)C WIROEAKAQSKZGH-BXUZGUMPSA-N 0.000 claims 1
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