TWI701246B - 作為ＬＲＲＫ２抑制劑之新穎咪唑並［４，５－ｃ］喹啉衍生物 - Google Patents

Info

Publication number

TWI701246B

TWI701246B TW107107734A TW107107734A TWI701246B TW I701246 B TWI701246 B TW I701246B TW 107107734 A TW107107734 A TW 107107734A TW 107107734 A TW107107734 A TW 107107734A TW I701246 B TWI701246 B TW I701246B

Authority

TW

Taiwan

Prior art keywords

methyl

imidazo

quinoline

chloro

pyran

Prior art date

2017-03-10

Links

• Espacenet
• Global Dossier
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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 4
• 229940124786 LRRK2 inhibitor Drugs 0.000 title description 6
• 150000001875 compounds Chemical class 0.000 claims abstract description 241
• 150000003839 salts Chemical class 0.000 claims abstract description 65
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 58
• 208000018737 Parkinson disease Diseases 0.000 claims abstract description 38
• 201000010099 disease Diseases 0.000 claims abstract description 38
• 208000011231 Crohn disease Diseases 0.000 claims abstract description 25
• 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 23
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 16
• 206010024229 Leprosy Diseases 0.000 claims abstract description 9
• -1 2,2-difluoropropyl Chemical group 0.000 claims description 186
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 141
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 127
• 239000000460 chlorine Substances 0.000 claims description 41
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 39
• 229910052801 chlorine Inorganic materials 0.000 claims description 39
• CIIFKVFOVFJZDM-UHFFFAOYSA-N quinoline-8-carbonitrile Chemical compound C1=CN=C2C(C#N)=CC=CC2=C1 CIIFKVFOVFJZDM-UHFFFAOYSA-N 0.000 claims description 34
• ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims description 19
• 206010012289 Dementia Diseases 0.000 claims description 15
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 14
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
• 239000003814 drug Substances 0.000 claims description 12
• 230000000750 progressive effect Effects 0.000 claims description 9
• 208000009829 Lewy Body Disease Diseases 0.000 claims description 8
• 201000002832 Lewy body dementia Diseases 0.000 claims description 8
• 229940079593 drug Drugs 0.000 claims description 8
• 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 claims description 8
• 201000011240 Frontotemporal dementia Diseases 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 7
• 206010033799 Paralysis Diseases 0.000 claims description 6
• 208000021090 palsy Diseases 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• 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 5
• 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 5
• 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 5
• 230000001054 cortical effect Effects 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 102000013498 tau Proteins Human genes 0.000 claims description 5
• 108010026424 tau Proteins Proteins 0.000 claims description 5
• 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
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
• 208000032859 Synucleinopathies Diseases 0.000 claims description 4
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
• HYOBIUULDPLKIE-UHFFFAOYSA-N (5-methylpyridin-2-yl)methanol Chemical compound CC1=CC=C(CO)N=C1 HYOBIUULDPLKIE-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
• 102000003802 alpha-Synuclein Human genes 0.000 claims description 3
• 108090000185 alpha-Synuclein Proteins 0.000 claims description 3
• 239000011737 fluorine Substances 0.000 claims description 3
• 229910052731 fluorine Inorganic materials 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• RONWGALEIBILOG-VMJVVOMYSA-N quinine sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 RONWGALEIBILOG-VMJVVOMYSA-N 0.000 claims description 3
• 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
• FVNAQFOFKZUYGE-INIZCTEOSA-N 1-[(3S)-4,4-difluoro-1-methylpyrrolidin-3-yl]-8-fluoro-2-[(4-methyltriazol-1-yl)methyl]imidazo[4,5-c]quinoline Chemical compound CC1=CN(CC2=NC(C=NC(C=C3)=C4C=C3F)=C4N2[C@@H](CN(C)C2)C2(F)F)N=N1 FVNAQFOFKZUYGE-INIZCTEOSA-N 0.000 claims description 2
• 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 description 2
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
• UCEKGUYEHHVQOO-UHFFFAOYSA-N 8-chloro-1-(2,2-difluoropropyl)-2-[(4-methoxypyrazol-1-yl)methyl]imidazo[4,5-c]quinoline Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3CC(C)(F)F)CN1N=CC(=C1)OC UCEKGUYEHHVQOO-UHFFFAOYSA-N 0.000 claims description 2
• JDBRPIUNCRNMES-UHFFFAOYSA-N 8-chloro-1-(2,2-dimethyloxan-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(N3C1CC(OCC1)(C)C)CN1N=CN=C1 JDBRPIUNCRNMES-UHFFFAOYSA-N 0.000 claims description 2
• KYZSJHQQVQXDRZ-CQSZACIVSA-N 8-chloro-1-[(3R)-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(N3[C@H]1CN(CC1)C)CN1N=NC(=C1)C KYZSJHQQVQXDRZ-CQSZACIVSA-N 0.000 claims description 2
• AFSJECQGCYZDGF-UHFFFAOYSA-N 8-chloro-2-[(4-cyclopropyltriazol-1-yl)methyl]-1-(3,3-difluorooxan-4-yl)imidazo[4,5-c]quinoline Chemical compound C1(=CC=C2N=CC3=C(N(C(=N3)CN3C=C(N=N3)C3CC3)C3CCOCC3(F)F)C2=C1)Cl AFSJECQGCYZDGF-UHFFFAOYSA-N 0.000 claims description 2
• KDPDGZZURNTOPN-MRXNPFEDSA-N 8-chloro-2-[(6-methylpyrimidin-4-yl)methyl]-1-[(3R)-1-methylpyrrolidin-3-yl]imidazo[4,5-c]quinoline Chemical compound ClC1=CC=2C3=C(C=NC=2C=C1)N=C(N3[C@H]1CN(CC1)C)CC1=NC=NC(=C1)C KDPDGZZURNTOPN-MRXNPFEDSA-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
• WYJBFPHJIUFSJH-KRWDZBQOSA-N 8-chloro-1-[(3S)-4,4-difluoro-1-methylpyrrolidin-3-yl]-2-[[4-(methoxymethyl)triazol-1-yl]methyl]imidazo[4,5-c]quinoline Chemical compound CN(C[C@@H]1N2C(C(C=C(C=C3)Cl)=C3N=C3)=C3N=C2CN2N=NC(COC)=C2)CC1(F)F WYJBFPHJIUFSJH-KRWDZBQOSA-N 0.000 claims 5
• KIMFZTFAVICDGC-HNNXBMFYSA-N 8-chloro-1-[(3S)-4,4-difluoro-1-methylpyrrolidin-3-yl]-2-(1,2,4-triazol-1-ylmethyl)imidazo[4,5-c]quinoline Chemical compound CN(C[C@@H]1N2C(C(C=C(C=C3)Cl)=C3N=C3)=C3N=C2CN2N=CN=C2)CC1(F)F KIMFZTFAVICDGC-HNNXBMFYSA-N 0.000 claims 4
• SXIUZTAWZDYLBB-KRWDZBQOSA-N 1-[(3S)-4,4-difluoro-1-methylpyrrolidin-3-yl]-2-[(4-methyltriazol-2-yl)methyl]imidazo[4,5-c]quinoline-8-carbonitrile Chemical compound CC1=NN(CC2=NC(C=NC(C=C3)=C4C=C3C#N)=C4N2[C@@H](CN(C)C2)C2(F)F)N=C1 SXIUZTAWZDYLBB-KRWDZBQOSA-N 0.000 claims 3
• CQCUMBBPDPDNLF-HNNXBMFYSA-N 1-[(3S)-4,4-difluoro-1-methylpyrrolidin-3-yl]-8-fluoro-2-(1,2,4-triazol-1-ylmethyl)imidazo[4,5-c]quinoline Chemical compound CN(C[C@@H]1N2C(C(C=C(C=C3)F)=C3N=C3)=C3N=C2CN2N=CN=C2)CC1(F)F CQCUMBBPDPDNLF-HNNXBMFYSA-N 0.000 claims 2
• XHJAOEKASUFHHN-UHFFFAOYSA-N 5-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=C=NC=C[CH]1 XHJAOEKASUFHHN-UHFFFAOYSA-N 0.000 claims 2
• WFTSBRRDDDLDRN-CRAIPNDOSA-N 8-chloro-1-[(2R,4R)-2-methyloxan-4-yl]-2-[(5-methylpyridin-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(C=C1)C WFTSBRRDDDLDRN-CRAIPNDOSA-N 0.000 claims 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 1
• 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 1
• 208000034799 Tauopathies Diseases 0.000 claims 1
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 1
• 102000009784 Leucine-Rich Repeat Serine-Threonine Protein Kinase-2 Human genes 0.000 abstract description 54
• 108010020246 Leucine-Rich Repeat Serine-Threonine Protein Kinase-2 Proteins 0.000 abstract description 54
• 208000015122 neurodegenerative disease Diseases 0.000 abstract description 6
• 206010028980 Neoplasm Diseases 0.000 abstract description 4
• 230000004770 neurodegeneration Effects 0.000 abstract description 3
• 201000011510 cancer Diseases 0.000 abstract description 2
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 266
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 245
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 236
• 239000000203 mixture Substances 0.000 description 133
• 239000000047 product Substances 0.000 description 117
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 114
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 107
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• 230000015572 biosynthetic process Effects 0.000 description 95
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• 238000005481 NMR spectroscopy Methods 0.000 description 88
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• 238000006243 chemical reaction Methods 0.000 description 65
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• 239000000908 ammonium hydroxide Substances 0.000 description 61
• 239000012044 organic layer Substances 0.000 description 59
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 58
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 58
• 229910002092 carbon dioxide Inorganic materials 0.000 description 55
• 239000001569 carbon dioxide Substances 0.000 description 54
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
• 238000005516 engineering process Methods 0.000 description 51
• 239000002904 solvent Substances 0.000 description 45
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 44
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• 229910052938 sodium sulfate Inorganic materials 0.000 description 39
• 235000011152 sodium sulphate Nutrition 0.000 description 39
• 238000004808 supercritical fluid chromatography Methods 0.000 description 39
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• 235000017557 sodium bicarbonate Nutrition 0.000 description 32
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