KR20140014133A - Bace1 및/또는 bace2 억제제로서의 1,4 옥사진 - Google Patents

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Publication number

KR20140014133A

KR20140014133A KR1020137021420A KR20137021420A KR20140014133A KR 20140014133 A KR20140014133 A KR 20140014133A KR 1020137021420 A KR1020137021420 A KR 1020137021420A KR 20137021420 A KR20137021420 A KR 20137021420A KR 20140014133 A KR20140014133 A KR 20140014133A

Authority

KR

South Korea

Prior art keywords

methyl

phenyl

dihydro

alkyl

fluoro

Prior art date

2011-01-18

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.)

Withdrawn

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• 239000003112 inhibitor Substances 0.000 title claims description 17
• 150000004896 1,4-oxazines Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 232
• 238000000034 method Methods 0.000 claims abstract description 66
• 102100021277 Beta-secretase 2 Human genes 0.000 claims abstract description 35
• 101000894883 Homo sapiens Beta-secretase 2 Proteins 0.000 claims abstract description 34
• 238000011282 treatment Methods 0.000 claims abstract description 33
• 102100021257 Beta-secretase 1 Human genes 0.000 claims abstract description 32
• 101000894895 Homo sapiens Beta-secretase 1 Proteins 0.000 claims abstract description 31
• 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 25
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 22
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 17
• 239000013543 active substance Substances 0.000 claims abstract description 12
• 230000002265 prevention Effects 0.000 claims abstract description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
• -1 -C 1 -6 - alkyl Chemical group 0.000 claims description 189
• 229910052736 halogen Inorganic materials 0.000 claims description 116
• 150000002367 halogens Chemical class 0.000 claims description 116
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 54
• 125000001424 substituent group Chemical group 0.000 claims description 47
• 125000000217 alkyl group Chemical group 0.000 claims description 41
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 38
• 125000001072 heteroaryl group Chemical group 0.000 claims description 34
• 125000003118 aryl group Chemical group 0.000 claims description 29
• 108010090849 Amyloid beta-Peptides Proteins 0.000 claims description 28
• 102000013455 Amyloid beta-Peptides Human genes 0.000 claims description 28
• 230000000694 effects Effects 0.000 claims description 27
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 25
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
• 125000000623 heterocyclic group Chemical group 0.000 claims description 24
• 201000010099 disease Diseases 0.000 claims description 23
• 150000003839 salts Chemical class 0.000 claims description 19
• 238000004519 manufacturing process Methods 0.000 claims description 16
• 238000002360 preparation method Methods 0.000 claims description 16
• 208000037259 Amyloid Plaque Diseases 0.000 claims description 14
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
• 239000003814 drug Substances 0.000 claims description 13
• 229910052739 hydrogen Inorganic materials 0.000 claims description 13
• 239000001257 hydrogen Substances 0.000 claims description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• 206010012601 diabetes mellitus Diseases 0.000 claims description 12
• 125000001153 fluoro group Chemical group F* 0.000 claims description 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
• 108010043324 Amyloid Precursor Protein Secretases Proteins 0.000 claims description 11
• 102000002659 Amyloid Precursor Protein Secretases Human genes 0.000 claims description 11
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
• 208000037765 diseases and disorders Diseases 0.000 claims description 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
• 238000011321 prophylaxis Methods 0.000 claims description 10
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 10
• 201000008319 inclusion body myositis Diseases 0.000 claims description 8
• 125000003545 alkoxy group Chemical group 0.000 claims description 7
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
• 206010008025 Cerebellar ataxia Diseases 0.000 claims description 6
• 201000010374 Down Syndrome Diseases 0.000 claims description 6
• 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 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• SNBVGRNXFMZUNZ-INIZCTEOSA-N (5r)-5-[5-(cyclopentylamino)-2-fluorophenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine Chemical compound C=1C(NC2CCCC2)=CC=C(F)C=1[C@]1(C)COCC(N)=N1 SNBVGRNXFMZUNZ-INIZCTEOSA-N 0.000 claims description 5
• 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• 206010006187 Breast cancer Diseases 0.000 claims description 5
• 208000026310 Breast neoplasm Diseases 0.000 claims description 5
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 5
• 206010028980 Neoplasm Diseases 0.000 claims description 5
• 125000003368 amide group Chemical group 0.000 claims description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 5
• 230000006806 disease prevention Effects 0.000 claims description 5
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 5
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
• 125000003107 substituted aryl group Chemical group 0.000 claims description 5
• MCRHAPLPANRVQW-UHFFFAOYSA-N 5-[3-[(1,2-dimethylbenzimidazol-5-yl)amino]phenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine Chemical compound C=1C=C2N(C)C(C)=NC2=CC=1NC(C=1)=CC=CC=1C1(C)COCC(N)=N1 MCRHAPLPANRVQW-UHFFFAOYSA-N 0.000 claims description 4
• BIQLWJAOBRCFDO-UHFFFAOYSA-N 5-[3-[(5-chloro-2,3-dihydro-1h-inden-1-yl)amino]phenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine Chemical compound C=1C=CC(NC2C3=CC=C(Cl)C=C3CC2)=CC=1C1(C)COCC(N)=N1 BIQLWJAOBRCFDO-UHFFFAOYSA-N 0.000 claims description 4
• 208000023275 Autoimmune disease Diseases 0.000 claims description 4
• 208000023328 Basedow disease Diseases 0.000 claims description 4
• 201000004624 Dermatitis Diseases 0.000 claims description 4
• 206010016228 Fasciitis Diseases 0.000 claims description 4
• 208000015023 Graves' disease Diseases 0.000 claims description 4
• 208000002972 Hepatolenticular Degeneration Diseases 0.000 claims description 4
• 208000023105 Huntington disease Diseases 0.000 claims description 4
• 208000003456 Juvenile Arthritis Diseases 0.000 claims description 4
• 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims description 4
• 208000007766 Kaposi sarcoma Diseases 0.000 claims description 4
• 208000034578 Multiple myelomas Diseases 0.000 claims description 4
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 4
• 208000006011 Stroke Diseases 0.000 claims description 4
• 208000018839 Wilson disease Diseases 0.000 claims description 4
• 239000002671 adjuvant Substances 0.000 claims description 4
• 206010003246 arthritis Diseases 0.000 claims description 4
• 230000001363 autoimmune Effects 0.000 claims description 4
• BVCRERJDOOBZOH-UHFFFAOYSA-N bicyclo[2.2.1]heptanyl Chemical group C1C[C+]2CC[C-]1C2 BVCRERJDOOBZOH-UHFFFAOYSA-N 0.000 claims description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 208000019069 chronic childhood arthritis Diseases 0.000 claims description 4
• 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 208000027866 inflammatory disease Diseases 0.000 claims description 4
• 230000028709 inflammatory response Effects 0.000 claims description 4
• 201000002215 juvenile rheumatoid arthritis Diseases 0.000 claims description 4
• 206010025135 lupus erythematosus Diseases 0.000 claims description 4
• 210000002540 macrophage Anatomy 0.000 claims description 4
• 201000001441 melanoma Diseases 0.000 claims description 4
• 208000010125 myocardial infarction Diseases 0.000 claims description 4
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
• RWCZTUDBYGQJTK-LZWOXQAQSA-N (1r,2s)-2-[3-[(3r)-5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl]-4-fluoroanilino]cyclopentan-1-ol Chemical compound C=1C(N[C@@H]2[C@@H](CCC2)O)=CC=C(F)C=1[C@]1(C)COCC(N)=N1 RWCZTUDBYGQJTK-LZWOXQAQSA-N 0.000 claims description 3
• RWCZTUDBYGQJTK-DZKIICNBSA-N (1s,2s)-2-[3-[(3r)-5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl]-4-fluoroanilino]cyclopentan-1-ol Chemical compound C=1C(N[C@@H]2[C@H](CCC2)O)=CC=C(F)C=1[C@]1(C)COCC(N)=N1 RWCZTUDBYGQJTK-DZKIICNBSA-N 0.000 claims description 3
• QRXTWNWAFMAMIP-AWEZNQCLSA-N (5r)-5-[2-fluoro-5-(1,2-oxazol-3-ylamino)phenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine Chemical compound C=1C(NC2=NOC=C2)=CC=C(F)C=1[C@]1(C)COCC(N)=N1 QRXTWNWAFMAMIP-AWEZNQCLSA-N 0.000 claims description 3
• FOMKAUKZKZNSRI-LBPRGKRZSA-N (5r)-5-[2-fluoro-5-(2,2,2-trifluoroethylamino)phenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine Chemical compound C=1C(NCC(F)(F)F)=CC=C(F)C=1[C@]1(C)COCC(N)=N1 FOMKAUKZKZNSRI-LBPRGKRZSA-N 0.000 claims description 3
• IDIJEPWZHXCJCL-LBPRGKRZSA-N (5r)-5-[2-fluoro-5-(2,2,3,3,3-pentafluoropropylamino)phenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine Chemical compound C=1C(NCC(F)(F)C(F)(F)F)=CC=C(F)C=1[C@]1(C)COCC(N)=N1 IDIJEPWZHXCJCL-LBPRGKRZSA-N 0.000 claims description 3
• YHBCCGYRJHZRIT-ZDUSSCGKSA-N (5r)-5-[2-fluoro-5-(3,3,3-trifluoropropylamino)phenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine Chemical compound C=1C(NCCC(F)(F)F)=CC=C(F)C=1[C@]1(C)COCC(N)=N1 YHBCCGYRJHZRIT-ZDUSSCGKSA-N 0.000 claims description 3
• VEBDOPAMPGWBDV-NBFOKTCDSA-N (5r)-5-[2-fluoro-5-(3-methylbutan-2-ylamino)phenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine Chemical class CC(C)C(C)NC1=CC=C(F)C([C@@]2(C)N=C(N)COC2)=C1 VEBDOPAMPGWBDV-NBFOKTCDSA-N 0.000 claims description 3
• VGSIYGKAKNKCHH-INIZCTEOSA-N (5r)-5-[2-fluoro-5-(3-methylbutylamino)phenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine Chemical compound CC(C)CCNC1=CC=C(F)C([C@@]2(C)N=C(N)COC2)=C1 VGSIYGKAKNKCHH-INIZCTEOSA-N 0.000 claims description 3
• HCGNKVLPKJMANG-HNNXBMFYSA-N (5r)-5-[2-fluoro-5-(3-methylsulfanylpropylamino)phenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine Chemical compound CSCCCNC1=CC=C(F)C([C@@]2(C)N=C(N)COC2)=C1 HCGNKVLPKJMANG-HNNXBMFYSA-N 0.000 claims description 3
• IUECETKEUARTFS-MHTVFEQDSA-N (5r)-5-[2-fluoro-5-(oxolan-3-ylamino)phenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine Chemical compound C=1C(NC2COCC2)=CC=C(F)C=1[C@]1(C)COCC(N)=N1 IUECETKEUARTFS-MHTVFEQDSA-N 0.000 claims description 3
• FZNGSQOVFGNTTD-INIZCTEOSA-N (5r)-5-[2-fluoro-5-(pentan-3-ylamino)phenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine Chemical compound CCC(CC)NC1=CC=C(F)C([C@@]2(C)N=C(N)COC2)=C1 FZNGSQOVFGNTTD-INIZCTEOSA-N 0.000 claims description 3
• FSAJCWVALVMAKW-WBMJQRKESA-N (5r)-5-[2-fluoro-5-[[(2r)-oxolan-2-yl]methylamino]phenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine Chemical compound C=1C(NC[C@@H]2OCCC2)=CC=C(F)C=1[C@]1(C)COCC(N)=N1 FSAJCWVALVMAKW-WBMJQRKESA-N 0.000 claims description 3
• PEKTURXUQVGPEG-NRFANRHFSA-N (5r)-5-[2-fluoro-5-[[3-(2,2,2-trifluoroethoxy)quinolin-8-yl]amino]phenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine Chemical compound C=1C(NC=2C3=NC=C(OCC(F)(F)F)C=C3C=CC=2)=CC=C(F)C=1[C@]1(C)COCC(N)=N1 PEKTURXUQVGPEG-NRFANRHFSA-N 0.000 claims description 3
• BAKRUGCZKCVDEM-QFIPXVFZSA-N (5r)-5-[2-fluoro-5-[[3-(2-fluoroethoxy)quinolin-8-yl]amino]phenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine Chemical compound C=1C(NC=2C3=NC=C(OCCF)C=C3C=CC=2)=CC=C(F)C=1[C@]1(C)COCC(N)=N1 BAKRUGCZKCVDEM-QFIPXVFZSA-N 0.000 claims description 3
• DSRMJUAEYUDBRT-ZDUSSCGKSA-N (5r)-5-[5-(2,2-difluoroethylamino)-2-fluorophenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine Chemical compound C=1C(NCC(F)F)=CC=C(F)C=1[C@]1(C)COCC(N)=N1 DSRMJUAEYUDBRT-ZDUSSCGKSA-N 0.000 claims description 3
• FMVKCRWWNAQUEF-HNNXBMFYSA-N (5r)-5-[5-(butylamino)-2-fluorophenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine Chemical compound CCCCNC1=CC=C(F)C([C@@]2(C)N=C(N)COC2)=C1 FMVKCRWWNAQUEF-HNNXBMFYSA-N 0.000 claims description 3
• KKLMFSIUUFHDAW-HNNXBMFYSA-N (5r)-5-[5-(cyclobutylamino)-2-fluorophenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine Chemical compound C=1C(NC2CCC2)=CC=C(F)C=1[C@]1(C)COCC(N)=N1 KKLMFSIUUFHDAW-HNNXBMFYSA-N 0.000 claims description 3
• MFIGRCBCTKHMRZ-KRWDZBQOSA-N (5r)-5-[5-(cyclohexylamino)-2-fluorophenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine Chemical compound C=1C(NC2CCCCC2)=CC=C(F)C=1[C@]1(C)COCC(N)=N1 MFIGRCBCTKHMRZ-KRWDZBQOSA-N 0.000 claims description 3
• ORNNHNZPHILLPY-HNNXBMFYSA-N (5r)-5-[5-(cyclopropylmethylamino)-2-fluorophenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine Chemical compound C=1C(NCC2CC2)=CC=C(F)C=1[C@]1(C)COCC(N)=N1 ORNNHNZPHILLPY-HNNXBMFYSA-N 0.000 claims description 3
• LBDVFEXBWOROJV-FQEVSTJZSA-N (5r)-5-[5-[(3,6-dichloroquinolin-8-yl)amino]-2-fluorophenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine Chemical compound C=1C(NC=2C3=NC=C(Cl)C=C3C=C(Cl)C=2)=CC=C(F)C=1[C@]1(C)COCC(N)=N1 LBDVFEXBWOROJV-FQEVSTJZSA-N 0.000 claims description 3
• QMXOUBXMBUQGFI-FQEVSTJZSA-N (5r)-5-[5-[(3-chloro-6-fluoroquinolin-8-yl)amino]-2-fluorophenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine Chemical compound C=1C(NC=2C3=NC=C(Cl)C=C3C=C(F)C=2)=CC=C(F)C=1[C@]1(C)COCC(N)=N1 QMXOUBXMBUQGFI-FQEVSTJZSA-N 0.000 claims description 3
• UCGIYSHWKADWCV-BDQAORGHSA-N (5r)-5-[5-[(3-chloro-6-fluoroquinolin-8-yl)amino]-2-fluorophenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine;hydrochloride Chemical compound Cl.C=1C(NC=2C3=NC=C(Cl)C=C3C=C(F)C=2)=CC=C(F)C=1[C@]1(C)COCC(N)=N1 UCGIYSHWKADWCV-BDQAORGHSA-N 0.000 claims description 3
• OSRJQZXSYLZQHL-BDQAORGHSA-N (5r)-5-[5-[(3-chloroquinolin-8-yl)amino]-2-fluorophenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine;hydrochloride Chemical compound Cl.C=1C(NC=2C3=NC=C(Cl)C=C3C=CC=2)=CC=C(F)C=1[C@]1(C)COCC(N)=N1 OSRJQZXSYLZQHL-BDQAORGHSA-N 0.000 claims description 3
• RUMTVFXUGDDVFV-FYZYNONXSA-N (5r)-5-[5-[2-(2,2-difluoroethoxy)anilino]-2-fluorophenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine;hydrochloride Chemical compound Cl.C=1C(NC=2C(=CC=CC=2)OCC(F)F)=CC=C(F)C=1[C@]1(C)COCC(N)=N1 RUMTVFXUGDDVFV-FYZYNONXSA-N 0.000 claims description 3
• XUDAQSPLHDYMTP-ANYOKISRSA-N (5r)-5-[5-[[1-(5-chloropyridin-2-yl)-2-methylpropyl]amino]-2-fluorophenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine Chemical compound C=1C=C(Cl)C=NC=1C(C(C)C)NC(C=1)=CC=C(F)C=1[C@]1(C)COCC(N)=N1 XUDAQSPLHDYMTP-ANYOKISRSA-N 0.000 claims description 3
• HLTYVBBHDLMJQB-DEOSSOPVSA-N (5r)-5-[5-[[3-(cyclopropylmethoxy)-6-fluoroquinolin-8-yl]amino]-2-fluorophenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine Chemical compound C=1C(NC=2C3=NC=C(OCC4CC4)C=C3C=C(F)C=2)=CC=C(F)C=1[C@]1(C)COCC(N)=N1 HLTYVBBHDLMJQB-DEOSSOPVSA-N 0.000 claims description 3
• UWJFBDWADBANMX-INIZCTEOSA-N (5r)-5-[5-[[4-chloro-1-(difluoromethyl)pyrazol-3-yl]methylamino]-2-fluorophenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine Chemical compound C=1C(NCC=2C(=CN(N=2)C(F)F)Cl)=CC=C(F)C=1[C@]1(C)COCC(N)=N1 UWJFBDWADBANMX-INIZCTEOSA-N 0.000 claims description 3
• JXUFFJSEYVIGAA-MLVYHOMMSA-N (5s)-5-[5-[(5-chloro-2,3-dihydro-1h-inden-1-yl)amino]-2-fluorophenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine;hydrochloride Chemical compound Cl.C=1C(NC2C3=CC=C(Cl)C=C3CC2)=CC=C(F)C=1[C@@]1(C)COCC(N)=N1 JXUFFJSEYVIGAA-MLVYHOMMSA-N 0.000 claims description 3
• TWQFDPFLUOXDSO-LJQANCHMSA-N (5s)-5-[5-[(6-chloro-1-methylindazol-3-yl)amino]-2-fluorophenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine Chemical compound C12=CC=C(Cl)C=C2N(C)N=C1NC(C=1)=CC=C(F)C=1[C@@]1(C)COCC(N)=N1 TWQFDPFLUOXDSO-LJQANCHMSA-N 0.000 claims description 3
• 125000005955 1H-indazolyl group Chemical group 0.000 claims description 3
• 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 3
• XIAJXBYPLFZIKS-UHFFFAOYSA-N 5-[3-[(2,4-dichlorophenyl)methylamino]phenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine Chemical compound C=1C=CC(NCC=2C(=CC(Cl)=CC=2)Cl)=CC=1C1(C)COCC(N)=N1 XIAJXBYPLFZIKS-UHFFFAOYSA-N 0.000 claims description 3
• WWCXRNBXEBTLSG-UHFFFAOYSA-N 5-[3-[(3-chloro-6-fluoroquinolin-8-yl)amino]phenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine Chemical compound C=1C=CC(NC=2C3=NC=C(Cl)C=C3C=C(F)C=2)=CC=1C1(C)COCC(N)=N1 WWCXRNBXEBTLSG-UHFFFAOYSA-N 0.000 claims description 3
• MNPQSOIYEJRNIW-UHFFFAOYSA-N 5-[3-[(3-chlorophenyl)methylamino]phenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine Chemical compound C=1C=CC(NCC=2C=C(Cl)C=CC=2)=CC=1C1(C)COCC(N)=N1 MNPQSOIYEJRNIW-UHFFFAOYSA-N 0.000 claims description 3
• MADKDOVWBWXDFY-UHFFFAOYSA-N 5-[3-[(3-chloroquinolin-8-yl)amino]phenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine;hydrochloride Chemical compound Cl.C=1C=CC(NC=2C3=NC=C(Cl)C=C3C=CC=2)=CC=1C1(C)COCC(N)=N1 MADKDOVWBWXDFY-UHFFFAOYSA-N 0.000 claims description 3
• SCTBKUXFMWEWHM-UHFFFAOYSA-N 5-[3-[(3-methoxyquinolin-8-yl)amino]phenyl]-5-methyl-2,6-dihydro-1,4-oxazin-3-amine;hydrochloride Chemical compound Cl.C=1C=CC2=CC(OC)=CN=C2C=1NC(C=1)=CC=CC=1C1(C)COCC(N)=N1 SCTBKUXFMWEWHM-UHFFFAOYSA-N 0.000 claims description 3
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