JP2013536179A5 - - Google Patents
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- Publication number
- JP2013536179A5 JP2013536179A5 JP2013521954A JP2013521954A JP2013536179A5 JP 2013536179 A5 JP2013536179 A5 JP 2013536179A5 JP 2013521954 A JP2013521954 A JP 2013521954A JP 2013521954 A JP2013521954 A JP 2013521954A JP 2013536179 A5 JP2013536179 A5 JP 2013536179A5
- Authority
- JP
- Japan
- Prior art keywords
- ylamino
- benzo
- oxazol
- methyl
- pyrimidin
- 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.)
- Granted
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- -1 -CF Three Chemical group 0.000 description 68
- 150000001875 compounds Chemical class 0.000 description 28
- 125000000217 alkyl group Chemical group 0.000 description 27
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 26
- 238000000034 method Methods 0.000 description 24
- 125000005605 benzo group Chemical group 0.000 description 18
- 125000004429 atom Chemical group 0.000 description 11
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 8
- 239000008194 pharmaceutical composition Substances 0.000 description 8
- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical compound C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 6
- 102000042838 JAK family Human genes 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- ITDXRIFHDJKTAA-UHFFFAOYSA-N 3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=C2OC(=O)NC2=C1 ITDXRIFHDJKTAA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- 125000002619 bicyclic group Chemical group 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 125000004404 heteroalkyl group Chemical group 0.000 description 4
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 208000023275 Autoimmune disease Diseases 0.000 description 3
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000001404 mediated effect Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- XQCZBXHVTFVIFE-UHFFFAOYSA-N 2-amino-4-hydroxypyrimidine Chemical compound NC1=NC=CC(O)=N1 XQCZBXHVTFVIFE-UHFFFAOYSA-N 0.000 description 2
- QKHQEETZGJUPOR-UHFFFAOYSA-N 2-methoxy-6-methyl-4-[[5-methyl-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidin-2-yl]amino]benzoic acid Chemical compound CC1=C(C(O)=O)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(C)=CN=2)=C1 QKHQEETZGJUPOR-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- BVMWIXWOIGJRGE-UHFFFAOYSA-N NP(O)=O Chemical group NP(O)=O BVMWIXWOIGJRGE-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 229910052805 deuterium Inorganic materials 0.000 description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000005241 heteroarylamino group Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- CQQBUBUDFYGWFV-UHFFFAOYSA-N 2,6-dimethyl-4-[[5-methyl-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidin-2-yl]amino]benzonitrile;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(NC=2C=C3NC(=O)OC3=CC=2)C(C)=CN=C1NC1=CC(C)=C(C#N)C(C)=C1 CQQBUBUDFYGWFV-UHFFFAOYSA-N 0.000 description 1
- HMHIINMUADBISS-UHFFFAOYSA-N 2-[4-[[5-methyl-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidin-2-yl]amino]phenyl]acetaldehyde Chemical compound N1=C(NC=2C=C3NC(=O)OC3=CC=2)C(C)=CN=C1NC1=CC=C(CC=O)C=C1 HMHIINMUADBISS-UHFFFAOYSA-N 0.000 description 1
- XKJMNBXQXFINKX-UHFFFAOYSA-N 2-fluoro-3-[[5-methyl-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidin-2-yl]amino]benzonitrile;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(NC=2C=C3NC(=O)OC3=CC=2)C(C)=CN=C1NC1=CC=CC(C#N)=C1F XKJMNBXQXFINKX-UHFFFAOYSA-N 0.000 description 1
- BLOBGYACHNZQHW-UHFFFAOYSA-N 2-methyl-6-[[5-methyl-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidin-2-yl]amino]pyridine-3-carbonitrile Chemical compound N1=C(NC=2C=C3NC(=O)OC3=CC=2)C(C)=CN=C1NC1=CC=C(C#N)C(C)=N1 BLOBGYACHNZQHW-UHFFFAOYSA-N 0.000 description 1
- PEWAIWRUUGVRFE-UHFFFAOYSA-N 3-[[5-chloro-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidin-2-yl]amino]-2-fluorobenzonitrile;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=C(C#N)C(F)=C1NC1=NC=C(Cl)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 PEWAIWRUUGVRFE-UHFFFAOYSA-N 0.000 description 1
- IANOZUTZODAJSM-UHFFFAOYSA-N 3-methyl-5-[[5-methyl-2-(3,4,5-trimethylanilino)pyrimidin-4-yl]amino]-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=C(C)C(C)=CC(NC=2N=C(NC=3C=C4N(C)C(=O)OC4=CC=3)C(C)=CN=2)=C1 IANOZUTZODAJSM-UHFFFAOYSA-N 0.000 description 1
- NZVKTUYSHCWKCL-UHFFFAOYSA-N 3h-1,3-oxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound O=C1NC=CO1.OC(=O)C(F)(F)F NZVKTUYSHCWKCL-UHFFFAOYSA-N 0.000 description 1
- KCUSGANGRWSONG-UHFFFAOYSA-N 4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]-2-(3,4,5-trimethylanilino)pyrimidine-5-carboxylic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=C(C)C(C)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(C(O)=O)=CN=2)=C1 KCUSGANGRWSONG-UHFFFAOYSA-N 0.000 description 1
- TZBLQBRLXLNABA-UHFFFAOYSA-N 4-[[5-fluoro-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidin-2-yl]amino]-2,6-dimethylbenzonitrile Chemical compound CC1=C(C#N)C(C)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(F)=CN=2)=C1 TZBLQBRLXLNABA-UHFFFAOYSA-N 0.000 description 1
- ICIDGNQYUIUUBW-UHFFFAOYSA-N 4-[[5-fluoro-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidin-2-yl]amino]-n-propan-2-ylbenzamide;formic acid Chemical compound OC=O.C1=CC(C(=O)NC(C)C)=CC=C1NC1=NC=C(F)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 ICIDGNQYUIUUBW-UHFFFAOYSA-N 0.000 description 1
- ZRTGMWRBMGQKKE-UHFFFAOYSA-N 4-methyl-6-[[5-methyl-4-[(2-oxo-3h-1,3-benzoxazol-5-yl)amino]pyrimidin-2-yl]amino]pyridine-3-carbonitrile Chemical compound N1=C(NC=2C=C3NC(=O)OC3=CC=2)C(C)=CN=C1NC1=CC(C)=C(C#N)C=N1 ZRTGMWRBMGQKKE-UHFFFAOYSA-N 0.000 description 1
- YLLIKDNBCSMBDD-UHFFFAOYSA-N 5-[(2-amino-5-fluoro-6-phenylpyrimidin-4-yl)amino]-3H-1,3-benzoxazol-2-one Chemical compound C1(=CC=CC=C1)C1=C(C(=NC(=N1)N)NC=1C=CC2=C(NC(O2)=O)C=1)F YLLIKDNBCSMBDD-UHFFFAOYSA-N 0.000 description 1
- BOKOUDYMWNXLGH-UHFFFAOYSA-N 5-[(2-anilino-5-chloropyrimidin-4-yl)amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(NC=2C=C3NC(=O)OC3=CC=2)C(Cl)=CN=C1NC1=CC=CC=C1 BOKOUDYMWNXLGH-UHFFFAOYSA-N 0.000 description 1
- BLKCWNVNVANBHP-UHFFFAOYSA-N 5-[(2-anilino-5-nitropyrimidin-4-yl)amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(NC=2C=C3NC(=O)OC3=CC=2)C([N+](=O)[O-])=CN=C1NC1=CC=CC=C1 BLKCWNVNVANBHP-UHFFFAOYSA-N 0.000 description 1
- LPHCLCMKBSJBDO-UHFFFAOYSA-N 5-[[2-(1,3-dihydro-2-benzofuran-5-ylamino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound C1=C2OC(=O)NC2=CC(NC2=NC(NC=3C=C4COCC4=CC=3)=NC=C2C)=C1 LPHCLCMKBSJBDO-UHFFFAOYSA-N 0.000 description 1
- DIKGXTRGYVCEIP-UHFFFAOYSA-N 5-[[2-(2,4-difluoro-3-methoxyanilino)-5-fluoropyrimidin-4-yl]amino]-7-fluoro-3h-1,3-benzoxazol-2-one Chemical compound COC1=C(F)C=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=C(F)C=3)C(F)=CN=2)=C1F DIKGXTRGYVCEIP-UHFFFAOYSA-N 0.000 description 1
- AYPFNIHHENCZOS-UHFFFAOYSA-N 5-[[2-(2,4-difluoro-3-methoxyanilino)-5-fluoropyrimidin-4-yl]amino]-7-methyl-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=C(F)C=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=C(C)C=3)C(F)=CN=2)=C1F AYPFNIHHENCZOS-UHFFFAOYSA-N 0.000 description 1
- BROZPOZIIOBNNZ-UHFFFAOYSA-N 5-[[2-(2,4-difluoro-3-methoxyanilino)-5-nitropyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=C(F)C=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(=CN=2)[N+]([O-])=O)=C1F BROZPOZIIOBNNZ-UHFFFAOYSA-N 0.000 description 1
- HWOSGLSHLHGNBR-UHFFFAOYSA-N 5-[[2-(2,4-difluoro-3-propan-2-yloxyanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound CC(C)OC1=C(F)C=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(C)=CN=2)=C1F HWOSGLSHLHGNBR-UHFFFAOYSA-N 0.000 description 1
- WQMZENQZLBGFSR-UHFFFAOYSA-N 5-[[2-(2-fluoro-3,4-dimethoxyanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound FC1=C(OC)C(OC)=CC=C1NC1=NC=C(C)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 WQMZENQZLBGFSR-UHFFFAOYSA-N 0.000 description 1
- VYAOXGKPFCICGJ-UHFFFAOYSA-N 5-[[2-(2-fluoro-3-methoxy-4-methylanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=C(C)C=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(C)=CN=2)=C1F VYAOXGKPFCICGJ-UHFFFAOYSA-N 0.000 description 1
- OKSYUCSOWVGFFQ-UHFFFAOYSA-N 5-[[2-(2-fluoro-3-methoxyanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound COC1=CC=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(C)=CN=2)=C1F OKSYUCSOWVGFFQ-UHFFFAOYSA-N 0.000 description 1
- KSCNGRQEMCGODB-UHFFFAOYSA-N 5-[[2-(2-fluoro-3-methoxyanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound COC1=CC=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C=CN=2)=C1F KSCNGRQEMCGODB-UHFFFAOYSA-N 0.000 description 1
- GVJPNCTVCUNHMF-UHFFFAOYSA-N 5-[[2-(2-fluoro-4-methoxyanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC1=CC(OC)=CC=C1NC1=NC=C(C)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 GVJPNCTVCUNHMF-UHFFFAOYSA-N 0.000 description 1
- WKJGVCNCTBQCBE-UHFFFAOYSA-N 5-[[2-(2-fluoro-5-methoxy-4-methylanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(C)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(C)=CN=2)=C1F WKJGVCNCTBQCBE-UHFFFAOYSA-N 0.000 description 1
- NEMMTUDMKUIEIH-UHFFFAOYSA-N 5-[[2-(3,4-diethoxy-2-fluoroanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound FC1=C(OCC)C(OCC)=CC=C1NC1=NC=C(C)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 NEMMTUDMKUIEIH-UHFFFAOYSA-N 0.000 description 1
- HUWBZBKNHFFQRB-UHFFFAOYSA-N 5-[[2-(3,4-dimethoxy-5-methylanilino)-5-fluoropyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=C(OC)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(F)=CN=2)=C1 HUWBZBKNHFFQRB-UHFFFAOYSA-N 0.000 description 1
- BNESUYMLWRMWOQ-UHFFFAOYSA-N 5-[[2-(3,4-dimethoxy-5-methylanilino)-5-fluoropyrimidin-4-yl]amino]-7-fluoro-3h-1,3-benzoxazol-2-one Chemical compound CC1=C(OC)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=C(F)C=3)C(F)=CN=2)=C1 BNESUYMLWRMWOQ-UHFFFAOYSA-N 0.000 description 1
- KEDJNSAGZCTYBO-UHFFFAOYSA-N 5-[[2-(3,4-dimethoxy-5-methylanilino)-5-fluoropyrimidin-4-yl]amino]-7-methyl-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=C(OC)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=C(C)C=3)C(F)=CN=2)=C1 KEDJNSAGZCTYBO-UHFFFAOYSA-N 0.000 description 1
- JMQUFKAINVANSW-UHFFFAOYSA-N 5-[[2-(3,5-difluoroanilino)pyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC1=CC(F)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C=CN=2)=C1 JMQUFKAINVANSW-UHFFFAOYSA-N 0.000 description 1
- GLCKZUYTFKFAMK-UHFFFAOYSA-N 5-[[2-(3,5-dimethoxy-4-methylanilino)-5-fluoropyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=C(C)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(F)=CN=2)=C1 GLCKZUYTFKFAMK-UHFFFAOYSA-N 0.000 description 1
- JVBYWYIIGLWBAS-UHFFFAOYSA-N 5-[[2-(3-amino-4-methoxyanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one Chemical compound C1=C(N)C(OC)=CC=C1NC1=NC=C(C)C(NC=2C=C3NC(=O)OC3=CC=2)=N1 JVBYWYIIGLWBAS-UHFFFAOYSA-N 0.000 description 1
- NTGRYWTYJPJSFJ-UHFFFAOYSA-N 5-[[2-(3-chloro-4,5-dimethoxyanilino)-5-fluoropyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.ClC1=C(OC)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(F)=CN=2)=C1 NTGRYWTYJPJSFJ-UHFFFAOYSA-N 0.000 description 1
- QHDWBLMOMGHAKK-UHFFFAOYSA-N 5-[[2-(3-ethenylanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(NC=2C=C3NC(=O)OC3=CC=2)C(C)=CN=C1NC1=CC=CC(C=C)=C1 QHDWBLMOMGHAKK-UHFFFAOYSA-N 0.000 description 1
- JJYGXMMABJKTPH-UHFFFAOYSA-N 5-[[2-(3-ethoxy-4,5-dimethylanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.CC1=C(C)C(OCC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(C)=CN=2)=C1 JJYGXMMABJKTPH-UHFFFAOYSA-N 0.000 description 1
- KUVHOKHWQZUWKO-UHFFFAOYSA-N 5-[[2-(3-fluoro-5-methoxy-4-methylanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC1=C(C)C(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(C)=CN=2)=C1 KUVHOKHWQZUWKO-UHFFFAOYSA-N 0.000 description 1
- AVKXPBUFMRDXEH-UHFFFAOYSA-N 5-[[2-(3-hydroxy-4,5-dimethylanilino)-5-methylpyrimidin-4-yl]amino]-3h-1,3-benzoxazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC1=C(C)C(C)=CC(NC=2N=C(NC=3C=C4NC(=O)OC4=CC=3)C(C)=CN=2)=C1 AVKXPBUFMRDXEH-UHFFFAOYSA-N 0.000 description 1
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| WO2016100452A2 (en) * | 2014-12-17 | 2016-06-23 | Celgene Avilomics Research, Inc. | Heteroaryl compounds and uses thereof |
| WO2017007658A1 (en) * | 2015-07-07 | 2017-01-12 | Rigel Pharmaceuticals, Inc. | A combination for immune mediated cancer treatment |
| WO2019040706A1 (en) * | 2017-08-24 | 2019-02-28 | Aclaris Therapeutics, Inc. | COMPOSITIONS AND METHODS FOR TREATING VITILIGO |
| JP7167146B2 (ja) * | 2017-11-06 | 2022-11-08 | ブリストル－マイヤーズ スクイブ カンパニー | Ｈｐｋ１阻害剤として有用なイソフラノン化合物 |
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