SG176311A1 - Methods of treating or preventing autoimmune diseases with 2,4-pyrimidinediamine compounds - Google Patents
Methods of treating or preventing autoimmune diseases with 2,4-pyrimidinediamine compounds Download PDFInfo
- Publication number
- SG176311A1 SG176311A1 SG2007044290A SG2007044290A SG176311A1 SG 176311 A1 SG176311 A1 SG 176311A1 SG 2007044290 A SG2007044290 A SG 2007044290A SG 2007044290 A SG2007044290 A SG 2007044290A SG 176311 A1 SG176311 A1 SG 176311A1
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- SG
- Singapore
- Prior art keywords
- fluoro
- pyrimidinediamine
- oxazin
- chloro
- benz
- Prior art date
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- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical class NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 title claims abstract description 93
- 208000023275 Autoimmune disease Diseases 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title abstract description 60
- 150000001875 compounds Chemical class 0.000 claims abstract description 228
- -1 (indol-6-yl)-2,4-pyrimidinediamine Chemical compound 0.000 claims description 144
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 62
- 150000003839 salts Chemical class 0.000 claims description 43
- 150000001204 N-oxides Chemical class 0.000 claims description 21
- 239000012453 solvate Substances 0.000 claims description 19
- 239000003814 drug Substances 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 6
- GMMWNTHAIOJBSD-UHFFFAOYSA-N 6-chloro-4-n-(2,3-dimethylphenyl)-2-n,2-n-dimethylpyrimidine-2,4-diamine Chemical compound CN(C)C1=NC(Cl)=CC(NC=2C(=C(C)C=CC=2)C)=N1 GMMWNTHAIOJBSD-UHFFFAOYSA-N 0.000 claims 2
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims 2
- HBQIGSXHEATPCO-NSHDSACASA-N (2s)-6-[[2-(3,5-dimethoxyanilino)-5-fluoropyrimidin-4-yl]amino]-2-methyl-4h-1,4-benzoxazin-3-one Chemical compound COC1=CC(OC)=CC(NC=2N=C(NC=3C=C4NC(=O)[C@H](C)OC4=CC=3)C(F)=CN=2)=C1 HBQIGSXHEATPCO-NSHDSACASA-N 0.000 claims 1
- URHOGOHPMZITGZ-JTQLQIEISA-N (2s)-6-[[2-(3-chloro-4-methoxyanilino)-5-fluoropyrimidin-4-yl]amino]-2-methyl-4h-1,4-benzoxazin-3-one Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=NC=C(F)C(NC=2C=C3NC(=O)[C@H](C)OC3=CC=2)=N1 URHOGOHPMZITGZ-JTQLQIEISA-N 0.000 claims 1
- WPSSXCXNCVBYRY-UHFFFAOYSA-N 1-[6-[[2-(3,5-dimethylanilino)-5-fluoropyrimidin-4-yl]amino]pyridin-2-yl]-3-methylurea Chemical compound CNC(=O)NC1=CC=CC(NC=2C(=CN=C(NC=3C=C(C)C=C(C)C=3)N=2)F)=N1 WPSSXCXNCVBYRY-UHFFFAOYSA-N 0.000 claims 1
- WWHHRSQFDJQJLL-UHFFFAOYSA-N 2,2-difluoro-6-[[5-fluoro-2-(1h-indol-6-ylamino)pyrimidin-4-yl]amino]-4h-1,4-benzoxazin-3-one Chemical compound O1C(F)(F)C(=O)NC2=CC(NC3=NC(NC=4C=C5NC=CC5=CC=4)=NC=C3F)=CC=C21 WWHHRSQFDJQJLL-UHFFFAOYSA-N 0.000 claims 1
- RAYTVMVTRSGXIE-UHFFFAOYSA-N 2,6-dichloro-4-[[4-(3-chloro-4-methoxyanilino)-5-fluoropyrimidin-2-yl]amino]phenol Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=NC(NC=2C=C(Cl)C(O)=C(Cl)C=2)=NC=C1F RAYTVMVTRSGXIE-UHFFFAOYSA-N 0.000 claims 1
- BIKPIKFJMIQPEH-UHFFFAOYSA-N 2,6-dichloro-4-[[4-[3-chloro-4-(trifluoromethoxy)anilino]-5-fluoropyrimidin-2-yl]amino]phenol Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1NC1=NC=C(F)C(NC=2C=C(Cl)C(OC(F)(F)F)=CC=2)=N1 BIKPIKFJMIQPEH-UHFFFAOYSA-N 0.000 claims 1
- WRKXZNVSWQTPJR-UHFFFAOYSA-N 2-chloro-4-[[4-(3-chloro-4-methoxyanilino)-5-fluoropyrimidin-2-yl]amino]-6-methylphenol Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=NC(NC=2C=C(Cl)C(O)=C(C)C=2)=NC=C1F WRKXZNVSWQTPJR-UHFFFAOYSA-N 0.000 claims 1
- QTBFLDJCDPVLMN-UHFFFAOYSA-N 2-n,4-n-bis(3-chloro-4-phenylmethoxyphenyl)-5-fluoropyrimidine-2,4-diamine Chemical compound N1=C(NC=2C=C(Cl)C(OCC=3C=CC=CC=3)=CC=2)C(F)=CN=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=C1 QTBFLDJCDPVLMN-UHFFFAOYSA-N 0.000 claims 1
- VLWMEHPZIQUQQA-UHFFFAOYSA-N 2-n-(3,5-dichloro-4-methoxyphenyl)-4-n-(3,4-dichlorophenyl)-5-fluoropyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(OC)=C(Cl)C=C1NC1=NC=C(F)C(NC=2C=C(Cl)C(Cl)=CC=2)=N1 VLWMEHPZIQUQQA-UHFFFAOYSA-N 0.000 claims 1
- UERNMQOBADDFJZ-UHFFFAOYSA-N 2-n-(3,5-dimethoxyphenyl)-5-fluoro-4-n-(1h-indol-6-yl)pyrimidine-2,4-diamine Chemical compound COC1=CC(OC)=CC(NC=2N=C(NC=3C=C4NC=CC4=CC=3)C(F)=CN=2)=C1 UERNMQOBADDFJZ-UHFFFAOYSA-N 0.000 claims 1
- SNAIRQQSNZJNFU-UHFFFAOYSA-N 2-n-(3-chloro-4-methoxy-5-methylphenyl)-4-n-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-fluoropyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(OC)=C(C)C=C1NC1=NC=C(F)C(NC=2C=C3OCCOC3=CC=2)=N1 SNAIRQQSNZJNFU-UHFFFAOYSA-N 0.000 claims 1
- GJUTVWMOCFOTDW-UHFFFAOYSA-N 2-n-(3-chloro-4-methoxy-5-methylphenyl)-4-n-(3-chloro-4-methoxyphenyl)-5-fluoropyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=NC(NC=2C=C(Cl)C(OC)=C(C)C=2)=NC=C1F GJUTVWMOCFOTDW-UHFFFAOYSA-N 0.000 claims 1
- DAIUKXQHJQJQBH-UHFFFAOYSA-N 2-n-(3-chloro-4-methoxyphenyl)-4-n-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-fluoropyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=NC=C(F)C(NC=2C=C3OCCOC3=CC=2)=N1 DAIUKXQHJQJQBH-UHFFFAOYSA-N 0.000 claims 1
- SYHCSAGALBGSSH-UHFFFAOYSA-N 2-n-(3-chloro-4-methoxyphenyl)-4-n-(3,3-dimethyl-2,4-dihydro-1,4-benzoxazin-6-yl)-5-fluoropyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=NC=C(F)C(NC=2C=C3NC(C)(C)COC3=CC=2)=N1 SYHCSAGALBGSSH-UHFFFAOYSA-N 0.000 claims 1
- MFKPORXMKXGEOY-UHFFFAOYSA-N 2-n-(3-chloro-4-methoxyphenyl)-5-fluoro-4-n-(1h-indol-6-yl)pyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=NC=C(F)C(NC=2C=C3NC=CC3=CC=2)=N1 MFKPORXMKXGEOY-UHFFFAOYSA-N 0.000 claims 1
- ZYFAAKXOOJLAIZ-UHFFFAOYSA-N 2-n-(4-amino-2h-chromen-6-yl)-4-n-(3,4-dichlorophenyl)-5-fluoropyrimidine-2,4-diamine Chemical compound C1=C2C(N)=CCOC2=CC=C1NC(N=1)=NC=C(F)C=1NC1=CC=C(Cl)C(Cl)=C1 ZYFAAKXOOJLAIZ-UHFFFAOYSA-N 0.000 claims 1
- MUFBXMIWSBRWHL-UHFFFAOYSA-N 2-n-(4-chloro-3,5-dimethylphenyl)-4-n-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-fluoropyrimidine-2,4-diamine Chemical compound CC1=C(Cl)C(C)=CC(NC=2N=C(NC=3C=C4OCCOC4=CC=3)C(F)=CN=2)=C1 MUFBXMIWSBRWHL-UHFFFAOYSA-N 0.000 claims 1
- ZIMQYCFCHZCBLR-UHFFFAOYSA-N 2-n-[3-chloro-4-(trifluoromethoxy)phenyl]-4-n-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-fluoropyrimidine-2,4-diamine Chemical compound N1=C(NC=2C=C3OCCOC3=CC=2)C(F)=CN=C1NC1=CC=C(OC(F)(F)F)C(Cl)=C1 ZIMQYCFCHZCBLR-UHFFFAOYSA-N 0.000 claims 1
- ZDNLTUPJWOIZSC-UHFFFAOYSA-N 3-[[4-[(6-aminopyridin-2-yl)amino]-5-fluoropyrimidin-2-yl]amino]phenol Chemical compound NC1=CC=CC(NC=2C(=CN=C(NC=3C=C(O)C=CC=3)N=2)F)=N1 ZDNLTUPJWOIZSC-UHFFFAOYSA-N 0.000 claims 1
- JKRPBXSHTPXRIL-UHFFFAOYSA-N 4-n-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-fluoro-2-n-(4-methoxy-3,5-dimethylphenyl)pyrimidine-2,4-diamine Chemical compound C1=C(C)C(OC)=C(C)C=C1NC1=NC=C(F)C(NC=2C=C3OCCOC3=CC=2)=N1 JKRPBXSHTPXRIL-UHFFFAOYSA-N 0.000 claims 1
- BIRXWUQTFPFRNE-UHFFFAOYSA-N 4-n-(3,3-dimethyl-2,4-dihydro-1,4-benzoxazin-6-yl)-2-n-(3,5-dimethylphenyl)-5-fluoropyrimidine-2,4-diamine Chemical compound CC1=CC(C)=CC(NC=2N=C(NC=3C=C4NC(C)(C)COC4=CC=3)C(F)=CN=2)=C1 BIRXWUQTFPFRNE-UHFFFAOYSA-N 0.000 claims 1
- PLVRZSLMWIQVQJ-UHFFFAOYSA-N 4-n-(3,3-dimethyl-2,4-dihydro-1,4-benzoxazin-6-yl)-5-fluoro-2-n-(1-methylindazol-6-yl)pyrimidine-2,4-diamine Chemical compound O1CC(C)(C)NC2=CC(NC=3C(F)=CN=C(N=3)NC3=CC=C4C=NN(C4=C3)C)=CC=C21 PLVRZSLMWIQVQJ-UHFFFAOYSA-N 0.000 claims 1
- WPSFTTARWOUHKK-UHFFFAOYSA-N 4-n-(3,3-dimethyl-2,4-dihydro-1,4-benzoxazin-6-yl)-5-fluoro-2-n-(1h-indazol-6-yl)pyrimidine-2,4-diamine Chemical compound C1=C2C=NNC2=CC(NC=2N=C(C(=CN=2)F)NC2=CC=C3OCC(NC3=C2)(C)C)=C1 WPSFTTARWOUHKK-UHFFFAOYSA-N 0.000 claims 1
- NSYTUXSXAWSORH-UHFFFAOYSA-N 4-n-(3,4-dichlorophenyl)-2-n-(3,5-dimethoxyphenyl)-5-fluoropyrimidine-2,4-diamine Chemical compound COC1=CC(OC)=CC(NC=2N=C(NC=3C=C(Cl)C(Cl)=CC=3)C(F)=CN=2)=C1 NSYTUXSXAWSORH-UHFFFAOYSA-N 0.000 claims 1
- VREFJIBSABYTPP-UHFFFAOYSA-N 4-n-(3,4-dichlorophenyl)-2-n-[2-[(dimethylamino)methyl]-1-benzofuran-5-yl]-5-fluoropyrimidine-2,4-diamine Chemical compound C=1C=C2OC(CN(C)C)=CC2=CC=1NC(N=1)=NC=C(F)C=1NC1=CC=C(Cl)C(Cl)=C1 VREFJIBSABYTPP-UHFFFAOYSA-N 0.000 claims 1
- KBDUTWQLYYBHBJ-UHFFFAOYSA-N 4-n-(3,4-dichlorophenyl)-5-fluoro-2-n-(1h-indol-6-yl)pyrimidine-2,4-diamine Chemical compound FC1=CN=C(NC=2C=C3NC=CC3=CC=2)N=C1NC1=CC=C(Cl)C(Cl)=C1 KBDUTWQLYYBHBJ-UHFFFAOYSA-N 0.000 claims 1
- DRGKEQUVGSOOSE-UHFFFAOYSA-N 4-n-(3-chloro-4-methoxyphenyl)-2-n-(3,5-dichloro-4-methoxyphenyl)-5-fluoropyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=NC(NC=2C=C(Cl)C(OC)=C(Cl)C=2)=NC=C1F DRGKEQUVGSOOSE-UHFFFAOYSA-N 0.000 claims 1
- KUEZYRLCMQCYSZ-UHFFFAOYSA-N 4-n-(3-chloro-4-methoxyphenyl)-2-n-(3,5-dichlorophenyl)-5-fluoropyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=NC(NC=2C=C(Cl)C=C(Cl)C=2)=NC=C1F KUEZYRLCMQCYSZ-UHFFFAOYSA-N 0.000 claims 1
- KPNUYYGPISKAMK-UHFFFAOYSA-N 4-n-(3-chloro-4-methoxyphenyl)-2-n-(3,5-dimethoxyphenyl)-5-fluoropyrimidine-2,4-diamine Chemical compound COC1=CC(OC)=CC(NC=2N=C(NC=3C=C(Cl)C(OC)=CC=3)C(F)=CN=2)=C1 KPNUYYGPISKAMK-UHFFFAOYSA-N 0.000 claims 1
- IIHTZKLORIVJGG-UHFFFAOYSA-N 4-n-(3-chloro-4-methoxyphenyl)-2-n-(3,5-dimethylphenyl)-5-fluoropyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=NC(NC=2C=C(C)C=C(C)C=2)=NC=C1F IIHTZKLORIVJGG-UHFFFAOYSA-N 0.000 claims 1
- PKZRNQOLWIXUAM-UHFFFAOYSA-N 4-n-(3-chloro-4-methoxyphenyl)-2-n-[2-[(dimethylamino)methyl]-1-benzofuran-5-yl]-5-fluoropyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=NC(NC=2C=C3C=C(CN(C)C)OC3=CC=2)=NC=C1F PKZRNQOLWIXUAM-UHFFFAOYSA-N 0.000 claims 1
- RJSRSEQHUZBROZ-UHFFFAOYSA-N 4-n-(3-chloro-4-methoxyphenyl)-5-fluoro-2-n-(1h-indol-6-yl)pyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=NC(NC=2C=C3NC=CC3=CC=2)=NC=C1F RJSRSEQHUZBROZ-UHFFFAOYSA-N 0.000 claims 1
- QNCZYJIUFWEMFB-UHFFFAOYSA-N 4-n-(3-chloro-4-methoxyphenyl)-5-fluoro-2-n-(1h-indol-6-yl)pyrimidine-2,4-diamine;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.C1=C(Cl)C(OC)=CC=C1NC1=NC(NC=2C=C3NC=CC3=CC=2)=NC=C1F QNCZYJIUFWEMFB-UHFFFAOYSA-N 0.000 claims 1
- GWHKEGYADNVCAW-UHFFFAOYSA-N 4-n-(3-chloro-4-methoxyphenyl)-5-fluoro-2-n-(3,4,5-trimethylphenyl)pyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=NC(NC=2C=C(C)C(C)=C(C)C=2)=NC=C1F GWHKEGYADNVCAW-UHFFFAOYSA-N 0.000 claims 1
- DEUUNLAKOKQGDK-UHFFFAOYSA-N 4-n-(3-chloro-4-methoxyphenyl)-5-fluoro-2-n-[2-(methylaminomethylidene)-3h-1-benzofuran-5-yl]pyrimidine-2,4-diamine Chemical compound C=1C=C2OC(=CNC)CC2=CC=1NC(N=1)=NC=C(F)C=1NC1=CC=C(OC)C(Cl)=C1 DEUUNLAKOKQGDK-UHFFFAOYSA-N 0.000 claims 1
- BOSMJAKAMUSUDI-UHFFFAOYSA-N 4-n-(3-chloro-4-methoxyphenyl)-5-fluoro-2-n-[3-methoxy-5-(trifluoromethyl)phenyl]pyrimidine-2,4-diamine Chemical compound FC(F)(F)C1=CC(OC)=CC(NC=2N=C(NC=3C=C(Cl)C(OC)=CC=3)C(F)=CN=2)=C1 BOSMJAKAMUSUDI-UHFFFAOYSA-N 0.000 claims 1
- JNGKLBMWQZMSDB-UHFFFAOYSA-N 4-n-(4-amino-2h-chromen-6-yl)-2-n-(3,4-dichlorophenyl)-5-fluoropyrimidine-2,4-diamine Chemical compound C1=C2C(N)=CCOC2=CC=C1NC(C(=CN=1)F)=NC=1NC1=CC=C(Cl)C(Cl)=C1 JNGKLBMWQZMSDB-UHFFFAOYSA-N 0.000 claims 1
- FCHHDTATGVHMKJ-UHFFFAOYSA-N 4-n-(4-amino-2h-chromen-6-yl)-2-n-(3,5-dichloro-4-methoxyphenyl)-5-fluoropyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(OC)=C(Cl)C=C1NC1=NC=C(F)C(NC=2C=C3C(N)=CCOC3=CC=2)=N1 FCHHDTATGVHMKJ-UHFFFAOYSA-N 0.000 claims 1
- JOJBOWRCLLHSSS-UHFFFAOYSA-N 4-n-(4-amino-2h-chromen-6-yl)-5-fluoro-2-n-(1h-indazol-6-yl)pyrimidine-2,4-diamine Chemical compound C1=C2C=NNC2=CC(NC=2N=C(C(=CN=2)F)NC2=CC=C3OCC=C(C3=C2)N)=C1 JOJBOWRCLLHSSS-UHFFFAOYSA-N 0.000 claims 1
- ZFQPTDCFDMJBAT-UHFFFAOYSA-N 4-n-(6-aminopyridin-2-yl)-2-n-[3-chloro-4-(trifluoromethoxy)phenyl]-5-fluoropyrimidine-2,4-diamine Chemical compound NC1=CC=CC(NC=2C(=CN=C(NC=3C=C(Cl)C(OC(F)(F)F)=CC=3)N=2)F)=N1 ZFQPTDCFDMJBAT-UHFFFAOYSA-N 0.000 claims 1
- SLJZGDNPURJLTF-UHFFFAOYSA-N 4-n-[3-chloro-4-(trifluoromethoxy)phenyl]-2-n-(3,5-dichloro-4-methoxyphenyl)-5-fluoropyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(OC)=C(Cl)C=C1NC1=NC=C(F)C(NC=2C=C(Cl)C(OC(F)(F)F)=CC=2)=N1 SLJZGDNPURJLTF-UHFFFAOYSA-N 0.000 claims 1
- YYVPZVKPGOMUML-UHFFFAOYSA-N 4-n-[3-chloro-4-(trifluoromethoxy)phenyl]-2-n-(3,5-dimethoxyphenyl)-5-fluoropyrimidine-2,4-diamine Chemical compound COC1=CC(OC)=CC(NC=2N=C(NC=3C=C(Cl)C(OC(F)(F)F)=CC=3)C(F)=CN=2)=C1 YYVPZVKPGOMUML-UHFFFAOYSA-N 0.000 claims 1
- YNTUAYXQEZFTOL-UHFFFAOYSA-N 5-[[4-(3-chloro-4-methoxyanilino)-5-fluoropyrimidin-2-yl]amino]-n,n-dimethyl-2,3-dihydro-1-benzofuran-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=NC(NC=2C=C3CC(OC3=CC=2)C(=O)N(C)C)=NC=C1F YNTUAYXQEZFTOL-UHFFFAOYSA-N 0.000 claims 1
- LQWUFGVGTPOXER-UHFFFAOYSA-N 5-[[4-[(2,2-difluoro-3-oxo-4h-1,4-benzoxazin-6-yl)amino]-5-fluoropyrimidin-2-yl]amino]-n-methyl-2,3-dihydro-1-benzofuran-2-carboxamide Chemical compound O1C(F)(F)C(=O)NC2=CC(NC=3C(F)=CN=C(N=3)NC=3C=C4CC(OC4=CC=3)C(=O)NC)=CC=C21 LQWUFGVGTPOXER-UHFFFAOYSA-N 0.000 claims 1
- IPFOCULTTIOACT-UHFFFAOYSA-N 5-[[4-[3-chloro-4-(trifluoromethoxy)anilino]-5-fluoropyrimidin-2-yl]amino]-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C=1C=C2OC(C(=O)O)CC2=CC=1NC(N=1)=NC=C(F)C=1NC1=CC=C(OC(F)(F)F)C(Cl)=C1 IPFOCULTTIOACT-UHFFFAOYSA-N 0.000 claims 1
- HIJGFKCJWYJIEZ-UHFFFAOYSA-N 5-[[4-[3-chloro-4-(trifluoromethoxy)anilino]-5-fluoropyrimidin-2-yl]amino]-n,n-dimethyl-2,3-dihydro-1-benzofuran-2-carboxamide Chemical compound C=1C=C2OC(C(=O)N(C)C)CC2=CC=1NC(N=1)=NC=C(F)C=1NC1=CC=C(OC(F)(F)F)C(Cl)=C1 HIJGFKCJWYJIEZ-UHFFFAOYSA-N 0.000 claims 1
- RZQCMBMDYAEPOW-UHFFFAOYSA-N 5-[[4-[3-chloro-4-(trifluoromethoxy)anilino]-5-fluoropyrimidin-2-yl]amino]-n-(2-hydroxyethyl)-2,3-dihydro-1-benzofuran-2-carboxamide Chemical compound C=1C=C2OC(C(=O)NCCO)CC2=CC=1NC(N=1)=NC=C(F)C=1NC1=CC=C(OC(F)(F)F)C(Cl)=C1 RZQCMBMDYAEPOW-UHFFFAOYSA-N 0.000 claims 1
- APBYTLURVYNTEC-UHFFFAOYSA-N 5-[[4-[3-chloro-4-(trifluoromethoxy)anilino]-5-fluoropyrimidin-2-yl]amino]-n-propan-2-yl-2,3-dihydro-1-benzofuran-2-carboxamide Chemical compound C=1C=C2OC(C(=O)NC(C)C)CC2=CC=1NC(N=1)=NC=C(F)C=1NC1=CC=C(OC(F)(F)F)C(Cl)=C1 APBYTLURVYNTEC-UHFFFAOYSA-N 0.000 claims 1
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