EA029224B1 - Бициклические гетероциклические производные в качестве ингибиторов бромодомена - Google Patents

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Publication number

EA029224B1

EA029224B1 EA201691404A EA201691404A EA029224B1 EA 029224 B1 EA029224 B1 EA 029224B1 EA 201691404 A EA201691404 A EA 201691404A EA 201691404 A EA201691404 A EA 201691404A EA 029224 B1 EA029224 B1 EA 029224B1

Authority

EA

Eurasian Patent Office

Prior art keywords

dimethylisoxazol

methoxy

pyridin

ylmethyl

quinolin

Prior art date

2014-01-09

Links

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• 102000001805 Bromodomains Human genes 0.000 title claims abstract description 34
• 108050009021 Bromodomains Proteins 0.000 title claims abstract description 32
• 239000003112 inhibitor Substances 0.000 title abstract description 16
• 125000002618 bicyclic heterocycle group Chemical group 0.000 title abstract description 14
• 150000001875 compounds Chemical class 0.000 claims abstract description 188
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 44
• 201000010099 disease Diseases 0.000 claims abstract description 29
• 150000003839 salts Chemical class 0.000 claims abstract description 24
• 238000011282 treatment Methods 0.000 claims abstract description 20
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
• 239000003937 drug carrier Substances 0.000 claims abstract description 3
• 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 3
• -1 aminoC 1 -C 6 alkyl Chemical group 0.000 claims description 196
• 125000000217 alkyl group Chemical group 0.000 claims description 47
• 125000005842 heteroatom Chemical group 0.000 claims description 25
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
• 229910052739 hydrogen Inorganic materials 0.000 claims description 21
• 239000000203 mixture Substances 0.000 claims description 21
• 239000001257 hydrogen Substances 0.000 claims description 20
• 125000001188 haloalkyl group Chemical group 0.000 claims description 18
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
• 125000001424 substituent group Chemical group 0.000 claims description 15
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
• 229910052757 nitrogen Inorganic materials 0.000 claims description 14
• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 125000000623 heterocyclic group Chemical group 0.000 claims description 13
• 125000002950 monocyclic group Chemical group 0.000 claims description 13
• 229920006395 saturated elastomer Polymers 0.000 claims description 13
• XISPDFMAOWZEQG-UHFFFAOYSA-N 4h-1,4-oxazin-3-one Chemical compound O=C1COC=CN1 XISPDFMAOWZEQG-UHFFFAOYSA-N 0.000 claims description 12
• 108090000623 proteins and genes Proteins 0.000 claims description 12
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
• 125000002619 bicyclic group Chemical group 0.000 claims description 10
• 102000004169 proteins and genes Human genes 0.000 claims description 9
• 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 9
• YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 claims description 8
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 8
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
• 125000003118 aryl group Chemical group 0.000 claims description 7
• 229910052736 halogen Inorganic materials 0.000 claims description 7
• MYUKUIKWOQHVEV-UHFFFAOYSA-N 6-(3,5-dimethyl-1,2-oxazol-4-yl)-3-(fluoromethyl)-7-methoxy-1-(pyridin-2-ylmethyl)quinolin-2-one Chemical compound CC1=NOC(=C1C=1C=C2C=C(C(N(C2=CC1OC)CC1=NC=CC=C1)=O)CF)C MYUKUIKWOQHVEV-UHFFFAOYSA-N 0.000 claims description 6
• 150000002367 halogens Chemical class 0.000 claims description 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• LXJALZKCPQXVIU-UHFFFAOYSA-N 6-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(pyridin-2-ylmethyl)-7-(trifluoromethoxy)quinolin-2-one Chemical compound CC1=NOC(=C1C=1C=C2C=CC(N(C2=CC1OC(F)(F)F)CC1=NC=CC=C1)=O)C LXJALZKCPQXVIU-UHFFFAOYSA-N 0.000 claims description 5
• NSXYBKLKNINDDK-UHFFFAOYSA-N 6-(3,5-dimethyl-1,2-oxazol-4-yl)-3-(hydroxymethyl)-7-methoxy-1-(pyridin-2-ylmethyl)quinolin-2-one Chemical compound CC1=NOC(=C1C=1C=C2C=C(C(N(C2=CC1OC)CC1=NC=CC=C1)=O)CO)C NSXYBKLKNINDDK-UHFFFAOYSA-N 0.000 claims description 5
• KORFDBDOHJBIRP-UHFFFAOYSA-N 6-(3,5-dimethyl-1,2-oxazol-4-yl)-7-methoxy-1-(pyridin-2-ylmethyl)-3-(2,2,2-trifluoro-1-hydroxyethyl)quinolin-2-one Chemical compound CC1=NOC(=C1C=1C=C2C=C(C(N(C2=CC1OC)CC1=NC=CC=C1)=O)C(C(F)(F)F)O)C KORFDBDOHJBIRP-UHFFFAOYSA-N 0.000 claims description 5
• YTYKYMMMBPRIIF-UHFFFAOYSA-N 7-methoxy-6-(4-methyl-2-oxo-1H-imidazol-3-yl)-1-(pyridin-2-ylmethyl)quinolin-2-one Chemical compound COC1=C(C=C2C=CC(N(C2=C1)CC1=NC=CC=C1)=O)N1C(NC=C1C)=O YTYKYMMMBPRIIF-UHFFFAOYSA-N 0.000 claims description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
• GAUJOEUMVMWRHY-UHFFFAOYSA-N 1-[(5-bromopyridin-2-yl)methyl]-6-(3,5-dimethyl-1,2-oxazol-4-yl)-7-methoxyquinolin-2-one Chemical compound COC1=CC2=C(C=CC(=O)N2CC2=NC=C(Br)C=C2)C=C1C1=C(C)ON=C1C GAUJOEUMVMWRHY-UHFFFAOYSA-N 0.000 claims description 4
• KPTUFHHCSRDDDG-UHFFFAOYSA-N 2-[1-[2-(4-chlorophenyl)ethyl]-6-(3,5-dimethyl-1,2-oxazol-4-yl)-7-methoxy-2-oxoquinolin-3-yl]acetonitrile Chemical compound ClC1=CC=C(C=C1)CCN1C(C(=CC2=CC(=C(C=C12)OC)C=1C(=NOC1C)C)CC#N)=O KPTUFHHCSRDDDG-UHFFFAOYSA-N 0.000 claims description 4
• SRAXNVFAMZBEBS-UHFFFAOYSA-N 3-[7-methoxy-2-oxo-1-(pyridin-2-ylmethyl)quinolin-6-yl]-4-methylpyrrole-2,5-dione Chemical compound COC1=CC2=C(C=CC(=O)N2CC2=NC=CC=C2)C=C1C1=C(C)C(=O)NC1=O SRAXNVFAMZBEBS-UHFFFAOYSA-N 0.000 claims description 4
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
• 125000005843 halogen group Chemical group 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 239000011593 sulfur Chemical group 0.000 claims description 4
• XWXWBZCBJCMSGC-UHFFFAOYSA-N 4-[1-(4-chlorophenyl)ethyl]-7-(3,5-dimethyl-1,2-oxazol-4-yl)-6-methoxy-1,4-benzoxazin-3-one Chemical compound ClC1=CC=C(C=C1)C(C)N1C2=C(OCC1=O)C=C(C(=C2)OC)C=2C(=NOC2C)C XWXWBZCBJCMSGC-UHFFFAOYSA-N 0.000 claims description 3
• MZQKAAFGKZDPDH-UHFFFAOYSA-N 6-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(2-piperazin-1-ylethoxy)-1-(pyridin-2-ylmethyl)quinolin-2-one Chemical compound CC1=NOC(=C1C=1C=C2C=CC(N(C2=CC=1OCCN1CCNCC1)CC1=NC=CC=C1)=O)C MZQKAAFGKZDPDH-UHFFFAOYSA-N 0.000 claims description 3
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
• 241001465754 Metazoa Species 0.000 claims description 3
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
• 125000004043 oxo group Chemical group O=* 0.000 claims description 3
• 229910052760 oxygen Inorganic materials 0.000 claims description 3
• 239000001301 oxygen Substances 0.000 claims description 3
• 125000003367 polycyclic group Chemical group 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• OKVJHDWHLOJXTR-UHFFFAOYSA-N 1-[(5-chloropyridin-2-yl)methyl]-6-(3,5-dimethyl-1,2-oxazol-4-yl)-7-methoxyquinolin-2-one Chemical compound COC1=C(C=C2C=CC(=O)N(CC3=NC=C(Cl)C=C3)C2=C1)C1=C(C)ON=C1C OKVJHDWHLOJXTR-UHFFFAOYSA-N 0.000 claims description 2
• CPFLWFFGELPZFS-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)ethyl]-6-(3,5-dimethyl-1,2-oxazol-4-yl)-7-methoxy-3-methyl-2-oxoquinoline-4-carbonitrile Chemical compound COC1=CC2=C(C=C1C1=C(C)ON=C1C)C(C#N)=C(C)C(=O)N2CCC1=CC=C(Cl)C=C1 CPFLWFFGELPZFS-UHFFFAOYSA-N 0.000 claims description 2
• PYOIYVGUPRUWBY-UHFFFAOYSA-N 3-cyclohexyl-6-(3,5-dimethyl-1,2-oxazol-4-yl)-7-methoxy-1-(pyridin-2-ylmethyl)quinolin-2-one Chemical compound COC1=C(C=C2C=C(C3CCCCC3)C(=O)N(CC3=NC=CC=C3)C2=C1)C1=C(C)ON=C1C PYOIYVGUPRUWBY-UHFFFAOYSA-N 0.000 claims description 2
• CZGFZOISWNSMHZ-UHFFFAOYSA-N 3-cyclohexyl-6-(3,5-dimethyl-1,2-oxazol-4-yl)-7-methoxy-1-(pyridin-3-ylmethyl)quinolin-2-one Chemical compound COC1=C(C=C2C=C(C3CCCCC3)C(=O)N(CC3=CN=CC=C3)C2=C1)C1=C(C)ON=C1C CZGFZOISWNSMHZ-UHFFFAOYSA-N 0.000 claims description 2
• GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 2
• 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims description 2
• XITXXHLWJQJXKF-UHFFFAOYSA-N 4-cyclopropyl-6-(3,5-dimethyl-1,2-oxazol-4-yl)-7-methoxy-1-(pyridin-2-ylmethyl)quinolin-2-one Chemical compound COC1=C(C=C2C(=CC(=O)N(CC3=NC=CC=C3)C2=C1)C1CC1)C1=C(C)ON=C1C XITXXHLWJQJXKF-UHFFFAOYSA-N 0.000 claims description 2
• QWHGJLDTLAGCNH-UHFFFAOYSA-N 6-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(pyridin-2-ylmethyl)-7-(2,2,2-trifluoroethoxy)quinolin-2-one Chemical compound CC1=C(C(C)=NO1)C1=C(OCC(F)(F)F)C=C2N(CC3=NC=CC=C3)C(=O)C=CC2=C1 QWHGJLDTLAGCNH-UHFFFAOYSA-N 0.000 claims description 2
• XBYHJLCRRMNGBC-UHFFFAOYSA-N 6-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(pyridin-2-ylmethyl)-7-(2-pyrrolidin-1-ylethoxy)quinolin-2-one Chemical compound CC1=C(C(C)=NO1)C1=C(OCCN2CCCC2)C=C2N(CC3=NC=CC=C3)C(=O)C=CC2=C1 XBYHJLCRRMNGBC-UHFFFAOYSA-N 0.000 claims description 2
• VIXRXOAGVCUAQA-UHFFFAOYSA-N 6-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(pyridin-2-ylmethyl)-7-(2-pyrrolidin-3-ylethoxy)quinolin-2-one hydrochloride Chemical compound Cl.Cc1noc(C)c1-c1cc2ccc(=O)n(Cc3ccccn3)c2cc1OCCC1CCNC1 VIXRXOAGVCUAQA-UHFFFAOYSA-N 0.000 claims description 2
• VPTNNSOPNCOHQZ-UHFFFAOYSA-N 6-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(5-fluoropyridin-2-yl)methyl]-7-methoxyquinolin-2-one Chemical compound COC1=C(C=C2C=CC(=O)N(CC3=NC=C(F)C=C3)C2=C1)C1=C(C)ON=C1C VPTNNSOPNCOHQZ-UHFFFAOYSA-N 0.000 claims description 2
• SHVRLTFEMRFZEX-UHFFFAOYSA-N 6-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[[5-(3,5-dimethyl-1H-pyrazol-4-yl)pyridin-2-yl]methyl]-7-methoxyquinolin-2-one Chemical compound CC1=NNC(=C1C=1C=CC(=NC=1)CN1C(C=CC2=CC(=C(C=C12)OC)C=1C(=NOC=1C)C)=O)C SHVRLTFEMRFZEX-UHFFFAOYSA-N 0.000 claims description 2
• SHZKPBLWFXRUTL-UHFFFAOYSA-N 6-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[[5-(3-hydroxypyrrolidin-1-yl)pyridin-2-yl]methyl]-7-methoxyquinolin-2-one Chemical compound CC1=NOC(=C1C=1C=C2C=CC(N(C2=CC=1OC)CC1=NC=C(C=C1)N1CC(CC1)O)=O)C SHZKPBLWFXRUTL-UHFFFAOYSA-N 0.000 claims description 2
• RINBISSAHMWINJ-UHFFFAOYSA-N 6-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(2-morpholin-4-ylethoxy)-1-(pyridin-2-ylmethyl)quinolin-2-one Chemical compound CC1=C(C(C)=NO1)C1=C(OCCN2CCOCC2)C=C2N(CC3=NC=CC=C3)C(=O)C=CC2=C1 RINBISSAHMWINJ-UHFFFAOYSA-N 0.000 claims description 2
• JMMFLKGFUBNAKA-UHFFFAOYSA-N 6-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(2-piperidin-4-ylethoxy)-1-(pyridin-2-ylmethyl)quinolin-2-one Chemical compound CC1=NOC(=C1C=1C=C2C=CC(N(C2=CC=1OCCC1CCNCC1)CC1=NC=CC=C1)=O)C JMMFLKGFUBNAKA-UHFFFAOYSA-N 0.000 claims description 2
• OCNSZVQUZYVHSE-UHFFFAOYSA-N 6-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(3-hydroxypropoxy)-1-(pyridin-2-ylmethyl)quinolin-2-one Chemical compound CC1=C(C(C)=NO1)C1=C(OCCCO)C=C2N(CC3=NC=CC=C3)C(=O)C=CC2=C1 OCNSZVQUZYVHSE-UHFFFAOYSA-N 0.000 claims description 2
• MSECAQWKZQGRFJ-UHFFFAOYSA-N 6-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(piperidin-4-ylmethoxy)-1-(pyridin-2-ylmethyl)quinolin-2-one Chemical compound CC1=C(C(C)=NO1)C1=C(OCC2CCNCC2)C=C2N(CC3=NC=CC=C3)C(=O)C=CC2=C1 MSECAQWKZQGRFJ-UHFFFAOYSA-N 0.000 claims description 2
• LRQMTAYPCJYDQT-UHFFFAOYSA-N 6-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(pyridin-4-ylmethoxy)-1-(pyridin-2-ylmethyl)quinolin-2-one Chemical compound CC1=C(C(C)=NO1)C1=C(OCC2=CC=NC=C2)C=C2N(CC3=NC=CC=C3)C(=O)C=CC2=C1 LRQMTAYPCJYDQT-UHFFFAOYSA-N 0.000 claims description 2
• UZFVAOBKSOQXCJ-UHFFFAOYSA-N 6-(3,5-dimethyl-1,2-oxazol-4-yl)-7-hydroxy-1-(pyridin-2-ylmethyl)quinolin-2-one Chemical compound CC1=C(C(C)=NO1)C1=C(O)C=C2N(CC3=NC=CC=C3)C(=O)C=CC2=C1 UZFVAOBKSOQXCJ-UHFFFAOYSA-N 0.000 claims description 2
• PTHHHBOKUUKKCL-UHFFFAOYSA-N 6-(3,5-dimethyl-1,2-oxazol-4-yl)-7-methoxy-1-(pyridin-2-ylmethyl)quinolin-2-one Chemical compound CC1=NOC(=C1C=1C=C2C=CC(N(C2=CC1OC)CC1=NC=CC=C1)=O)C PTHHHBOKUUKKCL-UHFFFAOYSA-N 0.000 claims description 2
• PJPGHCWTFMIYNV-UHFFFAOYSA-N 6-(3,5-dimethyl-1,2-oxazol-4-yl)-7-methoxy-1-[[5-(trifluoromethyl)pyridin-2-yl]methyl]quinolin-2-one Chemical compound CC1=NOC(=C1C=1C=C2C=CC(N(C2=CC1OC)CC1=NC=C(C=C1)C(F)(F)F)=O)C PJPGHCWTFMIYNV-UHFFFAOYSA-N 0.000 claims description 2
• WEDXMVNSVVPHTD-UHFFFAOYSA-N 6-(3,5-dimethyl-1,2-oxazol-4-yl)-7-methoxy-3,3-dimethyl-1-(pyridin-2-ylmethyl)-4H-quinolin-2-one Chemical compound COC1=C(C=C2CC(C)(C)C(=O)N(CC3=NC=CC=C3)C2=C1)C1=C(C)ON=C1C WEDXMVNSVVPHTD-UHFFFAOYSA-N 0.000 claims description 2
• YVGWSVHZXWFLIT-UHFFFAOYSA-N 6-(3,5-dimethyl-1,2-oxazol-4-yl)-7-methoxy-3-methyl-1-(pyridin-2-ylmethyl)quinolin-2-one Chemical compound COC1=C(C=C2C=C(C)C(=O)N(CC3=NC=CC=C3)C2=C1)C1=C(C)ON=C1C YVGWSVHZXWFLIT-UHFFFAOYSA-N 0.000 claims description 2
• QDBBNYPSXUHFNP-UHFFFAOYSA-N 6-(3,5-dimethyl-1,2-oxazol-4-yl)-7-methoxy-4,4-dimethyl-1-(pyridin-2-ylmethyl)-3H-quinolin-2-one Chemical compound COC1=C(C=C2C(=C1)N(CC1=NC=CC=C1)C(=O)CC2(C)C)C1=C(C)ON=C1C QDBBNYPSXUHFNP-UHFFFAOYSA-N 0.000 claims description 2
• QSUNKZHBZDXQPH-UHFFFAOYSA-N 6-(3,5-dimethyl-1H-pyrazol-4-yl)-7-methoxy-1-(pyridin-2-ylmethyl)quinolin-2-one Chemical compound COC1=C(C=C2C=CC(=O)N(CC3=NC=CC=C3)C2=C1)C1=C(C)NN=C1C QSUNKZHBZDXQPH-UHFFFAOYSA-N 0.000 claims description 2
• FMAMGYIAROUURS-UHFFFAOYSA-N 6-(3-cyclopropyl-5-methyl-1,2-oxazol-4-yl)-7-methoxy-1-(pyridin-2-ylmethyl)quinolin-2-one Chemical compound COC1=CC2=C(C=CC(=O)N2CC2=NC=CC=C2)C=C1C1=C(C)ON=C1C1CC1 FMAMGYIAROUURS-UHFFFAOYSA-N 0.000 claims description 2
• MVIRVQRPJWFQFE-UHFFFAOYSA-N 7-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(2-methoxyethoxy)-4-(pyridin-4-ylmethyl)-1,4-benzoxazin-3-one Chemical compound COCCOC1=CC2=C(OCC(=O)N2CC2=CC=NC=C2)C=C1C1=C(C)ON=C1C MVIRVQRPJWFQFE-UHFFFAOYSA-N 0.000 claims description 2
• QBTPRMLUXFBHHQ-UHFFFAOYSA-N 7-methoxy-6-(3-methyl-1,2-oxazol-4-yl)-1-(pyridin-2-ylmethyl)quinolin-2-one Chemical compound COC1=C(C=C2C=CC(N(C2=C1)CC1=NC=CC=C1)=O)C=1C(=NOC1)C QBTPRMLUXFBHHQ-UHFFFAOYSA-N 0.000 claims description 2
• PVYLWRLORWMUAF-UHFFFAOYSA-N 7-methoxy-6-(5-methyl-1,2-oxazol-4-yl)-1-(pyridin-2-ylmethyl)quinolin-2-one Chemical compound COC1=C(C=C2C=CC(N(C2=C1)CC1=NC=CC=C1)=O)C=1C=NOC1C PVYLWRLORWMUAF-UHFFFAOYSA-N 0.000 claims description 2
• 125000005336 allyloxy group Chemical group 0.000 claims description 2
• 238000002560 therapeutic procedure Methods 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 4
• HCKXDBNROSNPBE-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-6-(3,5-dimethyl-1,2-oxazol-4-yl)-7-methoxyquinolin-2-one Chemical compound COC1=CC2=C(C=CC(=O)N2CC2=CC=C(Cl)C=C2)C=C1C1=C(C)ON=C1C HCKXDBNROSNPBE-UHFFFAOYSA-N 0.000 claims 1
• FICAQKBMCKEFDI-UHFFFAOYSA-N 3,5-dimethyl-1,2-oxazole Chemical compound CC=1C=C(C)ON=1 FICAQKBMCKEFDI-UHFFFAOYSA-N 0.000 claims 1
• OAVYHERNZVHDFP-UHFFFAOYSA-N 6-(3,5-dimethyl-1,2-oxazol-4-yl)-7-(2-hydroxyethoxy)-1-(pyridin-2-ylmethyl)quinolin-2-one Chemical compound CC1=C(C(C)=NO1)C1=C(OCCO)C=C2N(CC3=NC=CC=C3)C(=O)C=CC2=C1 OAVYHERNZVHDFP-UHFFFAOYSA-N 0.000 claims 1
• CKUYRCCSVXHUOC-UHFFFAOYSA-N 6-(3,5-dimethyl-1,2-oxazol-4-yl)-7-methoxy-1-(pyridin-2-ylmethyl)-3-(2,2,2-trifluoro-1,1-dihydroxyethyl)quinolin-2-one Chemical compound COC1=CC2=C(C=C1C1=C(C)ON=C1C)C=C(C(=O)N2CC1=NC=CC=C1)C(O)(O)C(F)(F)F CKUYRCCSVXHUOC-UHFFFAOYSA-N 0.000 claims 1
• NYUQSBMYDSDDRN-UHFFFAOYSA-N 6-(3,5-dimethyl-1,2-oxazol-4-yl)-7-methoxy-1-[[5-(1-methylpyrazol-4-yl)pyridin-2-yl]methyl]quinolin-2-one Chemical compound CC1=NOC(=C1C=1C=C2C=CC(N(C2=CC=1OC)CC1=NC=C(C=C1)C=1C=NN(C=1)C)=O)C NYUQSBMYDSDDRN-UHFFFAOYSA-N 0.000 claims 1
• DPUPISKTXKGYQU-UHFFFAOYSA-N 6-(3,5-dimethyl-1,2-oxazol-4-yl)-7-piperidin-4-yloxy-1-(pyridin-2-ylmethyl)quinolin-2-one Chemical compound CC1=NOC(=C1C=1C=C2C=CC(N(C2=CC=1OC1CCNCC1)CC1=NC=CC=C1)=O)C DPUPISKTXKGYQU-UHFFFAOYSA-N 0.000 claims 1
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