JP2010520875A5 - - Google Patents
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- JP2010520875A5 JP2010520875A5 JP2009552762A JP2009552762A JP2010520875A5 JP 2010520875 A5 JP2010520875 A5 JP 2010520875A5 JP 2009552762 A JP2009552762 A JP 2009552762A JP 2009552762 A JP2009552762 A JP 2009552762A JP 2010520875 A5 JP2010520875 A5 JP 2010520875A5
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- Japan
- Prior art keywords
- methyl
- oxo
- hydroxy
- dihydro
- ethyl
- 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.)
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 34
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 201000010099 disease Diseases 0.000 claims description 16
- 230000001404 mediated effect Effects 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- -1 hydroxy, amino Chemical group 0.000 claims description 14
- 208000037765 diseases and disorders Diseases 0.000 claims description 12
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
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- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 8
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- 125000003118 aryl group Chemical group 0.000 claims description 6
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
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- 150000003839 salts Chemical class 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
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- VIFCIENBDYQQDX-LLVKDONJSA-N (2r)-2-[6-chloro-1-oxo-5-[[2-[4-(trifluoromethyl)phenyl]acetyl]amino]isoquinolin-2-yl]propanamide Chemical compound ClC1=CC=C2C(=O)N([C@@H](C(N)=O)C)C=CC2=C1NC(=O)CC1=CC=C(C(F)(F)F)C=C1 VIFCIENBDYQQDX-LLVKDONJSA-N 0.000 claims description 4
- OPGCMPGPBPRTCR-SNVBAGLBSA-N (2r)-2-[6-chloro-5-[[2-(4-chloro-2-fluorophenyl)acetyl]amino]-1-oxoisoquinolin-2-yl]propanamide Chemical compound ClC1=CC=C2C(=O)N([C@@H](C(N)=O)C)C=CC2=C1NC(=O)CC1=CC=C(Cl)C=C1F OPGCMPGPBPRTCR-SNVBAGLBSA-N 0.000 claims description 4
- MZMRGDSURPETPD-SNVBAGLBSA-N (2r)-2-[6-chloro-5-[[2-[2-fluoro-3-(trifluoromethyl)phenyl]acetyl]amino]-1-oxoisoquinolin-2-yl]propanamide Chemical compound ClC1=CC=C2C(=O)N([C@@H](C(N)=O)C)C=CC2=C1NC(=O)CC1=CC=CC(C(F)(F)F)=C1F MZMRGDSURPETPD-SNVBAGLBSA-N 0.000 claims description 4
- KGUURNWYZWNORB-GFCCVEGCSA-N (2r)-2-[6-methoxy-1-oxo-5-[[2-[4-(trifluoromethyl)phenyl]acetyl]amino]isoquinolin-2-yl]propanamide Chemical compound COC1=CC=C(C(N([C@H](C)C(N)=O)C=C2)=O)C2=C1NC(=O)CC1=CC=C(C(F)(F)F)C=C1 KGUURNWYZWNORB-GFCCVEGCSA-N 0.000 claims description 4
- VIFCIENBDYQQDX-NSHDSACASA-N (2s)-2-[6-chloro-1-oxo-5-[[2-[4-(trifluoromethyl)phenyl]acetyl]amino]isoquinolin-2-yl]propanamide Chemical compound ClC1=CC=C2C(=O)N([C@H](C(N)=O)C)C=CC2=C1NC(=O)CC1=CC=C(C(F)(F)F)C=C1 VIFCIENBDYQQDX-NSHDSACASA-N 0.000 claims description 4
- WKSFDYRQJMJNFR-NWDGAFQWSA-N (2s)-n-[2-[(2r)-1-amino-1-oxopropan-2-yl]-6-chloro-1-oxoisoquinolin-5-yl]-2-(4-chlorophenyl)propanamide Chemical compound C1([C@@H](C(=O)NC=2C3=C(C(N([C@H](C)C(N)=O)C=C3)=O)C=CC=2Cl)C)=CC=C(Cl)C=C1 WKSFDYRQJMJNFR-NWDGAFQWSA-N 0.000 claims description 4
- UFSZNGPKJWFSHR-CYBMUJFWSA-N 2-(4-chloro-3-fluorophenyl)-n-[2-[(2r)-1-hydroxypropan-2-yl]-6-methyl-1-oxoisoquinolin-5-yl]acetamide Chemical compound CC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(Cl)C(F)=C1 UFSZNGPKJWFSHR-CYBMUJFWSA-N 0.000 claims description 4
- NNKBOZOTRMTPFO-LLVKDONJSA-N 2-(4-chloro-3-fluorophenyl)-n-[6-chloro-2-[(2r)-1-hydroxypropan-2-yl]-1-oxoisoquinolin-5-yl]acetamide Chemical compound ClC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(Cl)C(F)=C1 NNKBOZOTRMTPFO-LLVKDONJSA-N 0.000 claims description 4
- OHYAXGAMZSGPOJ-UHFFFAOYSA-N 2-[2-fluoro-3-(trifluoromethyl)phenyl]-n-[2-(2-hydroxyethyl)-6-(2-hydroxyethylamino)-1-oxoisoquinolin-5-yl]acetamide Chemical compound OCCNC1=CC=C(C(N(CCO)C=C2)=O)C2=C1NC(=O)CC1=CC=CC(C(F)(F)F)=C1F OHYAXGAMZSGPOJ-UHFFFAOYSA-N 0.000 claims description 4
- LKZDPAFXWXYVCK-UHFFFAOYSA-N 2-[2-fluoro-3-(trifluoromethyl)phenyl]-n-[2-(2-hydroxyethyl)-6-methyl-1-oxoisoquinolin-5-yl]acetamide Chemical compound CC1=CC=C(C(N(CCO)C=C2)=O)C2=C1NC(=O)CC1=CC=CC(C(F)(F)F)=C1F LKZDPAFXWXYVCK-UHFFFAOYSA-N 0.000 claims description 4
- VSGLANORJMNZRC-CYBMUJFWSA-N 2-[2-fluoro-3-(trifluoromethyl)phenyl]-n-[2-[(2r)-1-hydroxypropan-2-yl]-6-methyl-1-oxoisoquinolin-5-yl]acetamide Chemical compound CC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=CC(C(F)(F)F)=C1F VSGLANORJMNZRC-CYBMUJFWSA-N 0.000 claims description 4
- BDROBZBNYQZUKM-GFCCVEGCSA-N 2-[3-fluoro-4-(trifluoromethyl)phenyl]-n-[2-[(2r)-1-hydroxypropan-2-yl]-6-methoxy-1-oxoisoquinolin-5-yl]acetamide Chemical compound COC1=CC=C(C(N([C@H](C)CO)C=C2)=O)C2=C1NC(=O)CC1=CC=C(C(F)(F)F)C(F)=C1 BDROBZBNYQZUKM-GFCCVEGCSA-N 0.000 claims description 4
- JECILOFRRYCNDH-CYBMUJFWSA-N 2-[3-fluoro-4-(trifluoromethyl)phenyl]-n-[2-[(2r)-1-hydroxypropan-2-yl]-6-methyl-1-oxoisoquinolin-5-yl]acetamide Chemical compound CC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(C(F)(F)F)C(F)=C1 JECILOFRRYCNDH-CYBMUJFWSA-N 0.000 claims description 4
- QGYFHOFGDBIVEE-HNNXBMFYSA-N 2-[3-fluoro-4-(trifluoromethyl)phenyl]-n-[6-methyl-1-oxo-2-[(3s)-pyrrolidin-3-yl]isoquinolin-5-yl]acetamide Chemical compound C=1C=C(C(F)(F)F)C(F)=CC=1CC(=O)NC=1C(C)=CC=C(C2=O)C=1C=CN2[C@H]1CCNC1 QGYFHOFGDBIVEE-HNNXBMFYSA-N 0.000 claims description 4
- UTSFTJWRTXSFSI-CYBMUJFWSA-N 2-[4-fluoro-3-(trifluoromethyl)phenyl]-n-[2-[(2r)-1-hydroxypropan-2-yl]-6-methyl-1-oxoisoquinolin-5-yl]acetamide Chemical compound CC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(F)C(C(F)(F)F)=C1 UTSFTJWRTXSFSI-CYBMUJFWSA-N 0.000 claims description 4
- BHWBPMXJZHATJD-HNNXBMFYSA-N 2-[4-fluoro-3-(trifluoromethyl)phenyl]-n-[6-methyl-1-oxo-2-[(3s)-pyrrolidin-3-yl]isoquinolin-5-yl]acetamide Chemical compound C=1C=C(F)C(C(F)(F)F)=CC=1CC(=O)NC=1C(C)=CC=C(C2=O)C=1C=CN2[C@H]1CCNC1 BHWBPMXJZHATJD-HNNXBMFYSA-N 0.000 claims description 4
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- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
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- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
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- XJRFFZIYWHIBPY-UHFFFAOYSA-N n-[6-chloro-2-(2-hydroxyethyl)-1-oxoisoquinolin-5-yl]-2-[2-fluoro-3-(trifluoromethyl)phenyl]acetamide Chemical compound ClC1=CC=C2C(=O)N(CCO)C=CC2=C1NC(=O)CC1=CC=CC(C(F)(F)F)=C1F XJRFFZIYWHIBPY-UHFFFAOYSA-N 0.000 claims description 4
- ZXOKHTSAKAOOLZ-UHFFFAOYSA-N n-[6-chloro-2-(2-hydroxyethyl)-1-oxoisoquinolin-5-yl]-2-[3-fluoro-4-(trifluoromethyl)phenyl]acetamide Chemical compound ClC1=CC=C2C(=O)N(CCO)C=CC2=C1NC(=O)CC1=CC=C(C(F)(F)F)C(F)=C1 ZXOKHTSAKAOOLZ-UHFFFAOYSA-N 0.000 claims description 4
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- OTKCYGCETOSQLA-LLVKDONJSA-N n-[6-chloro-2-[(2r)-1-hydroxypropan-2-yl]-1-oxoisoquinolin-5-yl]-2-(3,4-dichlorophenyl)acetamide Chemical compound ClC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(Cl)C(Cl)=C1 OTKCYGCETOSQLA-LLVKDONJSA-N 0.000 claims description 4
- LAUUQYWKAHXBPX-LLVKDONJSA-N n-[6-chloro-2-[(2r)-1-hydroxypropan-2-yl]-1-oxoisoquinolin-5-yl]-2-[2-fluoro-4-(trifluoromethyl)phenyl]acetamide Chemical compound ClC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(C(F)(F)F)C=C1F LAUUQYWKAHXBPX-LLVKDONJSA-N 0.000 claims description 4
- FMOOSLMLRAUSBH-LLVKDONJSA-N n-[6-chloro-2-[(2r)-1-hydroxypropan-2-yl]-1-oxoisoquinolin-5-yl]-2-[3-fluoro-4-(trifluoromethyl)phenyl]acetamide Chemical compound ClC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(C(F)(F)F)C(F)=C1 FMOOSLMLRAUSBH-LLVKDONJSA-N 0.000 claims description 4
- SOXLIWHVZZQEKK-LLVKDONJSA-N n-[6-chloro-2-[(2r)-1-hydroxypropan-2-yl]-1-oxoisoquinolin-5-yl]-2-[4-fluoro-3-(trifluoromethyl)phenyl]acetamide Chemical compound ClC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(F)C(C(F)(F)F)=C1 SOXLIWHVZZQEKK-LLVKDONJSA-N 0.000 claims description 4
- GFMGLRZDRMQUJJ-CYBMUJFWSA-N n-[6-cyclopropyl-2-[(2r)-1-hydroxypropan-2-yl]-1-oxoisoquinolin-5-yl]-2-[3-fluoro-4-(trifluoromethyl)phenyl]acetamide Chemical compound C1CC1C1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(C(F)(F)F)C(F)=C1 GFMGLRZDRMQUJJ-CYBMUJFWSA-N 0.000 claims description 4
- 230000003959 neuroinflammation Effects 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- AYLWRSUFLVTPDR-UHFFFAOYSA-N 2-[3-fluoro-4-(trifluoromethyl)phenyl]-n-[2-(2-hydroxyethyl)-6-methyl-1-oxoisoquinolin-5-yl]acetamide Chemical compound CC1=CC=C(C(N(CCO)C=C2)=O)C2=C1NC(=O)CC1=CC=C(C(F)(F)F)C(F)=C1 AYLWRSUFLVTPDR-UHFFFAOYSA-N 0.000 claims description 3
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- NPYWIUPZYUTEAK-GFCCVEGCSA-N (2r)-2-[5-[[2-[3-fluoro-4-(trifluoromethyl)phenyl]acetyl]amino]-6-methyl-1-oxoisoquinolin-2-yl]propanamide Chemical compound CC1=CC=C2C(=O)N([C@@H](C(N)=O)C)C=CC2=C1NC(=O)CC1=CC=C(C(F)(F)F)C(F)=C1 NPYWIUPZYUTEAK-GFCCVEGCSA-N 0.000 claims description 2
- YMFPTJMPYCNHKO-ASXFNGKXSA-N 2-(1-adamantyl)-n-[2-[(2r)-1-hydroxypropan-2-yl]-6-methyl-1-oxoisoquinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=C2C=CN([C@@H](CO)C)C(=O)C2=CC=C1C YMFPTJMPYCNHKO-ASXFNGKXSA-N 0.000 claims description 2
- IXZKBFCFFLHLOH-CQSZACIVSA-N 2-[(2r)-1-hydroxypropan-2-yl]-6-methyl-1-oxo-n-[[3-(trifluoromethyl)phenyl]methyl]isoquinoline-5-carboxamide Chemical compound CC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1C(=O)NCC1=CC=CC(C(F)(F)F)=C1 IXZKBFCFFLHLOH-CQSZACIVSA-N 0.000 claims description 2
- GVNUVQYGCQUSSM-OAHLLOKOSA-N 2-[3-fluoro-4-(trifluoromethyl)phenyl]-n-[2-[(2r)-1-(3-hydroxyazetidin-1-yl)propan-2-yl]-6-methyl-1-oxoisoquinolin-5-yl]acetamide Chemical compound C([C@@H](C)N1C(C2=CC=C(C)C(NC(=O)CC=3C=C(F)C(=CC=3)C(F)(F)F)=C2C=C1)=O)N1CC(O)C1 GVNUVQYGCQUSSM-OAHLLOKOSA-N 0.000 claims description 2
- JECILOFRRYCNDH-ZDUSSCGKSA-N 2-[3-fluoro-4-(trifluoromethyl)phenyl]-n-[2-[(2s)-1-hydroxypropan-2-yl]-6-methyl-1-oxoisoquinolin-5-yl]acetamide Chemical compound CC1=CC=C2C(=O)N([C@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(C(F)(F)F)C(F)=C1 JECILOFRRYCNDH-ZDUSSCGKSA-N 0.000 claims description 2
- FFEPLNNDVFVTTR-QGZVFWFLSA-N 2-[3-fluoro-4-(trifluoromethyl)phenyl]-n-[6-methyl-1-oxo-2-[(2r)-1-piperazin-1-ylpropan-2-yl]isoquinolin-5-yl]acetamide Chemical compound C([C@@H](C)N1C(C2=CC=C(C)C(NC(=O)CC=3C=C(F)C(=CC=3)C(F)(F)F)=C2C=C1)=O)N1CCNCC1 FFEPLNNDVFVTTR-QGZVFWFLSA-N 0.000 claims description 2
- PSTNSIKFKNCGHB-CQSZACIVSA-N 2-[3-fluoro-4-(trifluoromethyl)phenyl]-n-[6-methyl-2-[(2r)-1-(methylamino)propan-2-yl]-1-oxoisoquinolin-5-yl]acetamide Chemical compound CC1=CC=C2C(=O)N([C@H](C)CNC)C=CC2=C1NC(=O)CC1=CC=C(C(F)(F)F)C(F)=C1 PSTNSIKFKNCGHB-CQSZACIVSA-N 0.000 claims description 2
- CSYHHBNQBKHTNI-UHFFFAOYSA-N 2-[3-fluoro-4-(trifluoromethyl)phenyl]-n-[6-methyl-2-[2-(methylamino)ethyl]-1-oxoisoquinolin-5-yl]acetamide Chemical compound CC1=CC=C2C(=O)N(CCNC)C=CC2=C1NC(=O)CC1=CC=C(C(F)(F)F)C(F)=C1 CSYHHBNQBKHTNI-UHFFFAOYSA-N 0.000 claims description 2
- AAMIKLACARMFCS-UHFFFAOYSA-N 2-[4-fluoro-3-(trifluoromethyl)phenyl]-n-[2-(2-hydroxyethyl)-6-methyl-1-oxoisoquinolin-5-yl]acetamide Chemical compound CC1=CC=C(C(N(CCO)C=C2)=O)C2=C1NC(=O)CC1=CC=C(F)C(C(F)(F)F)=C1 AAMIKLACARMFCS-UHFFFAOYSA-N 0.000 claims description 2
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2008
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- 2008-03-07 CN CN200880014110.6A patent/CN101686680B/zh active Active
- 2008-03-07 DK DK08726672.2T patent/DK2124562T3/en active
- 2008-03-07 JP JP2009552762A patent/JP2010520875A/ja active Pending
- 2008-03-07 WO PCT/US2008/003175 patent/WO2008112205A1/en not_active Ceased
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- 2008-03-07 ES ES08726672.2T patent/ES2576643T3/es active Active
- 2008-03-07 CA CA2680275A patent/CA2680275C/en not_active Expired - Fee Related