CA3056030A1 - Novel imidazo[4,5-c]quinoline derivatives as lrrk2 inhibitors - Google Patents
Novel imidazo[4,5-c]quinoline derivatives as lrrk2 inhibitors Download PDFInfo
- 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
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- CA
- Canada
- Prior art keywords
- methyl
- imidazo
- quinoline
- chloro
- pyran
- Prior art date
- 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
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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 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
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- 238000005550 wet granulation Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762469756P | 2017-03-10 | 2017-03-10 | |
| US62/469,756 | 2017-03-10 | ||
| US201862629152P | 2018-02-12 | 2018-02-12 | |
| US62/629,152 | 2018-02-12 | ||
| PCT/IB2018/051439 WO2018163066A1 (en) | 2017-03-10 | 2018-03-06 | Novel imidazo[4,5-c]quinoline derivatives as lrrk2 inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA3056030A1 true CA3056030A1 (en) | 2018-09-13 |
Family
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Family Applications (1)
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| CA3056030A Pending CA3056030A1 (en) | 2017-03-10 | 2018-03-06 | Novel imidazo[4,5-c]quinoline derivatives as lrrk2 inhibitors |
Country Status (13)
| Country | Link |
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| US (1) | US11312713B2 (enExample) |
| EP (1) | EP3592741B1 (enExample) |
| JP (1) | JP7219223B2 (enExample) |
| KR (1) | KR102582626B1 (enExample) |
| CN (1) | CN111051304B (enExample) |
| AU (1) | AU2018230236B2 (enExample) |
| BR (1) | BR112019018688A2 (enExample) |
| CA (1) | CA3056030A1 (enExample) |
| IL (1) | IL269214B (enExample) |
| MX (1) | MX2019010756A (enExample) |
| SG (2) | SG11201908322WA (enExample) |
| TW (1) | TWI701246B (enExample) |
| WO (1) | WO2018163066A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115728413A (zh) * | 2022-11-09 | 2023-03-03 | 内蒙古帕默康创医疗仪器有限公司 | 舍曲林血药浓度的定量分析方法 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PE20230612A1 (es) | 2020-05-06 | 2023-04-13 | Servier Lab | Nuevos inhibidores macrociclicos de la quinasa de lrrk2 |
| JP2023549682A (ja) | 2020-10-29 | 2023-11-29 | メルク・シャープ・アンド・ドーム・エルエルシー | Ｌｒｒｋ２阻害薬としてのｎ－結合イソキノリンアミド、医薬組成物及びその使用 |
| AU2022239815A1 (en) | 2021-03-18 | 2023-09-21 | Les Laboratoires Servier | Macrocyclic lrrk2 kinase inhibitors |
| CA3256816A1 (en) * | 2022-05-12 | 2023-11-16 | Interline Therapeutics, Inc. | LRRK2 INHIBITORS |
| JP2025517688A (ja) * | 2022-05-12 | 2025-06-10 | インターライン セラピューティクス インコーポレイティド | Ｌｒｒｋ２阻害剤 |
| CN116879450A (zh) * | 2023-07-25 | 2023-10-13 | 江苏汉邦科技股份有限公司 | 一种利用超临界流体色谱系统分离纯化芦可替尼前体的方法 |
| CN118440041B (zh) * | 2024-07-02 | 2024-09-27 | 苏州凯瑞医药科技有限公司 | 一种手性4-氨基-3-羟基四氢吡喃的制备方法 |
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2018
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- 2018-03-06 CN CN201880029989.5A patent/CN111051304B/zh active Active
- 2018-03-06 KR KR1020197029735A patent/KR102582626B1/ko active Active
- 2018-03-06 AU AU2018230236A patent/AU2018230236B2/en active Active
- 2018-03-06 MX MX2019010756A patent/MX2019010756A/es unknown
- 2018-03-06 CA CA3056030A patent/CA3056030A1/en active Pending
- 2018-03-06 WO PCT/IB2018/051439 patent/WO2018163066A1/en not_active Ceased
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- 2018-03-06 SG SG11201908322W patent/SG11201908322WA/en unknown
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- 2018-03-06 JP JP2019549462A patent/JP7219223B2/ja active Active
- 2018-03-07 TW TW107107734A patent/TWI701246B/zh active
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2019
- 2019-09-09 IL IL269214A patent/IL269214B/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115728413A (zh) * | 2022-11-09 | 2023-03-03 | 内蒙古帕默康创医疗仪器有限公司 | 舍曲林血药浓度的定量分析方法 |
Also Published As
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|---|---|
| KR20190138793A (ko) | 2019-12-16 |
| CN111051304B (zh) | 2022-12-27 |
| SG10202110112TA (en) | 2021-10-28 |
| TWI701246B (zh) | 2020-08-11 |
| MX2019010756A (es) | 2020-01-20 |
| AU2018230236B2 (en) | 2022-05-19 |
| US11312713B2 (en) | 2022-04-26 |
| NZ757971A (en) | 2024-12-20 |
| WO2018163066A1 (en) | 2018-09-13 |
| JP2020510046A (ja) | 2020-04-02 |
| IL269214B (en) | 2022-03-01 |
| SG11201908322WA (en) | 2019-10-30 |
| KR102582626B1 (ko) | 2023-09-22 |
| EP3592741B1 (en) | 2023-02-15 |
| JP7219223B2 (ja) | 2023-02-07 |
| AU2018230236A1 (en) | 2019-10-31 |
| EP3592741A1 (en) | 2020-01-15 |
| RU2019131727A (ru) | 2021-04-12 |
| US20210355117A1 (en) | 2021-11-18 |
| TW201900642A (zh) | 2019-01-01 |
| RU2019131727A3 (enExample) | 2021-04-26 |
| CN111051304A (zh) | 2020-04-21 |
| BR112019018688A2 (pt) | 2020-04-07 |
| IL269214A (en) | 2019-11-28 |
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