JP2011515462A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2011515462A5 JP2011515462A5 JP2011501736A JP2011501736A JP2011515462A5 JP 2011515462 A5 JP2011515462 A5 JP 2011515462A5 JP 2011501736 A JP2011501736 A JP 2011501736A JP 2011501736 A JP2011501736 A JP 2011501736A JP 2011515462 A5 JP2011515462 A5 JP 2011515462A5
- Authority
- JP
- Japan
- Prior art keywords
- difluoromethyl
- morpholinyl
- triazin
- chloroacetyl
- methoxy
- 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.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 claims 45
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 16
- 239000008194 pharmaceutical composition Substances 0.000 claims 13
- -1 cyano, amino Chemical group 0.000 claims 12
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 12
- 125000001072 heteroaryl group Chemical group 0.000 claims 11
- 125000000623 heterocyclic group Chemical group 0.000 claims 11
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 11
- 125000003118 aryl group Chemical group 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 10
- 239000000203 mixture Substances 0.000 claims 10
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims 8
- 125000003386 piperidinyl group Chemical group 0.000 claims 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 8
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 5
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 239000000651 prodrug Substances 0.000 claims 4
- 229940002612 prodrug Drugs 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 125000005647 linker group Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 102000010400 1-phosphatidylinositol-3-kinase activity proteins Human genes 0.000 claims 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 108091007960 PI3Ks Proteins 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 150000004677 hydrates Chemical class 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 239000006186 oral dosage form Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000004317 1,3,5-triazin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=N1 0.000 claims 1
- SZAXWOHJCJANOJ-UHFFFAOYSA-N 1-[4-[4-(2-aminopyrimidin-5-yl)-6-morpholin-4-yl-1,3,5-triazin-2-yl]piperazin-1-yl]-2-chloroethanone Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=NC(N2CCN(CC2)C(=O)CCl)=N1 SZAXWOHJCJANOJ-UHFFFAOYSA-N 0.000 claims 1
- BLXAMOAYWDXAMQ-UHFFFAOYSA-N 1-[4-[4-(2-aminopyrimidin-5-yl)-6-pyridin-4-yl-1,3,5-triazin-2-yl]piperazin-1-yl]-2-chloroethanone Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCN(CC2)C(=O)CCl)=NC(C=2C=CN=CC=2)=N1 BLXAMOAYWDXAMQ-UHFFFAOYSA-N 0.000 claims 1
- WGILTLOWHNKIHY-UHFFFAOYSA-N 1-[4-[4-(6-aminopyridin-3-yl)-6-morpholin-4-yl-1,3,5-triazin-2-yl]piperazin-1-yl]-2-chloroethanone Chemical compound C1=NC(N)=CC=C1C1=NC(N2CCOCC2)=NC(N2CCN(CC2)C(=O)CCl)=N1 WGILTLOWHNKIHY-UHFFFAOYSA-N 0.000 claims 1
- XRNNCVZJKZOBFY-UHFFFAOYSA-N 1-[4-[4-(6-aminopyridin-3-yl)-6-pyridin-4-yl-1,3,5-triazin-2-yl]piperazin-1-yl]-2-chloroethanone Chemical compound C1=NC(N)=CC=C1C1=NC(N2CCN(CC2)C(=O)CCl)=NC(C=2C=CN=CC=2)=N1 XRNNCVZJKZOBFY-UHFFFAOYSA-N 0.000 claims 1
- BLKITOAQWRRBKL-UHFFFAOYSA-N 2,2,2-trichloro-1-[4-[4-[2-(difluoromethyl)-4-methoxybenzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]piperazin-1-yl]ethanone Chemical compound FC(F)C1=NC=2C(OC)=CC=CC=2N1C(N=1)=NC(N2CCOCC2)=NC=1N1CCN(C(=O)C(Cl)(Cl)Cl)CC1 BLKITOAQWRRBKL-UHFFFAOYSA-N 0.000 claims 1
- VCLOHGYRTQVRPV-UHFFFAOYSA-N 2,2-dichloro-1-[4-[4-[2-(difluoromethyl)-4-methoxybenzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]piperazin-1-yl]ethanone Chemical compound FC(F)C1=NC=2C(OC)=CC=CC=2N1C(N=1)=NC(N2CCOCC2)=NC=1N1CCN(C(=O)C(Cl)Cl)CC1 VCLOHGYRTQVRPV-UHFFFAOYSA-N 0.000 claims 1
- DTBYHKPKFQPMIR-UHFFFAOYSA-N 2-chloro-1-[3-[[4-[2-(difluoromethyl)-4-methoxybenzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]-methylamino]azetidin-1-yl]ethanone Chemical compound FC(F)C1=NC=2C(OC)=CC=CC=2N1C(N=1)=NC(N(C)C2CN(C2)C(=O)CCl)=NC=1N1CCOCC1 DTBYHKPKFQPMIR-UHFFFAOYSA-N 0.000 claims 1
- UIYDDCFSHZHMLI-UHFFFAOYSA-N 2-chloro-1-[3-[[4-[2-(difluoromethyl)-4-methoxybenzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]amino]azetidin-1-yl]ethanone Chemical compound FC(F)C1=NC=2C(OC)=CC=CC=2N1C(N=C(N=1)N2CCOCC2)=NC=1NC1CN(C(=O)CCl)C1 UIYDDCFSHZHMLI-UHFFFAOYSA-N 0.000 claims 1
- UABFLXOFYDMLQA-UHFFFAOYSA-N 2-chloro-1-[4-[4-(1h-indazol-4-yl)-6-morpholin-4-yl-1,3,5-triazin-2-yl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)CCl)CCN1C1=NC(N2CCOCC2)=NC(C=2C=3C=NNC=3C=CC=2)=N1 UABFLXOFYDMLQA-UHFFFAOYSA-N 0.000 claims 1
- JACRHFNBXLLWGC-UHFFFAOYSA-N 2-chloro-1-[4-[4-(1h-indazol-4-yl)-6-pyridin-4-yl-1,3,5-triazin-2-yl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)CCl)CCN1C1=NC(C=2C=CN=CC=2)=NC(C=2C=3C=NNC=3C=CC=2)=N1 JACRHFNBXLLWGC-UHFFFAOYSA-N 0.000 claims 1
- QATBQFBTMUNHLA-UHFFFAOYSA-N 2-chloro-1-[4-[4-(3-hydroxyphenyl)-6-morpholin-4-yl-1,3,5-triazin-2-yl]piperazin-1-yl]ethanone Chemical compound OC1=CC=CC(C=2N=C(N=C(N=2)N2CCOCC2)N2CCN(CC2)C(=O)CCl)=C1 QATBQFBTMUNHLA-UHFFFAOYSA-N 0.000 claims 1
- NTAWEQHYZARGKO-UHFFFAOYSA-N 2-chloro-1-[4-[4-(3-hydroxyphenyl)-6-pyridin-4-yl-1,3,5-triazin-2-yl]piperazin-1-yl]ethanone Chemical compound OC1=CC=CC(C=2N=C(N=C(N=2)N2CCN(CC2)C(=O)CCl)C=2C=CN=CC=2)=C1 NTAWEQHYZARGKO-UHFFFAOYSA-N 0.000 claims 1
- CXXCZJFWDZWVTM-UHFFFAOYSA-N 2-chloro-1-[4-[4-[2-(difluoromethyl)-4-ethoxybenzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]piperazin-1-yl]ethanone Chemical compound FC(F)C1=NC=2C(OCC)=CC=CC=2N1C(N=1)=NC(N2CCOCC2)=NC=1N1CCN(C(=O)CCl)CC1 CXXCZJFWDZWVTM-UHFFFAOYSA-N 0.000 claims 1
- SPADOUNWWMPTEU-UHFFFAOYSA-N 2-chloro-1-[4-[4-[2-(difluoromethyl)-4-ethoxybenzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]piperidin-1-yl]ethanone Chemical compound FC(F)C1=NC=2C(OCC)=CC=CC=2N1C(N=1)=NC(C2CCN(CC2)C(=O)CCl)=NC=1N1CCOCC1 SPADOUNWWMPTEU-UHFFFAOYSA-N 0.000 claims 1
- RWLWZTIQTOPOJI-UHFFFAOYSA-N 2-chloro-1-[4-[4-[2-(difluoromethyl)-4-ethoxybenzimidazol-1-yl]-6-pyridin-4-yl-1,3,5-triazin-2-yl]piperazin-1-yl]ethanone Chemical compound FC(F)C1=NC=2C(OCC)=CC=CC=2N1C(N=1)=NC(N2CCN(CC2)C(=O)CCl)=NC=1C1=CC=NC=C1 RWLWZTIQTOPOJI-UHFFFAOYSA-N 0.000 claims 1
- VPXOGZBTJSRFTJ-UHFFFAOYSA-N 2-chloro-1-[4-[4-[2-(difluoromethyl)-4-hydroxybenzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]piperazin-1-yl]ethanone Chemical compound FC(F)C1=NC=2C(O)=CC=CC=2N1C(N=1)=NC(N2CCOCC2)=NC=1N1CCN(C(=O)CCl)CC1 VPXOGZBTJSRFTJ-UHFFFAOYSA-N 0.000 claims 1
- ASTLEWBNLRJQNE-UHFFFAOYSA-N 2-chloro-1-[4-[4-[2-(difluoromethyl)-4-hydroxybenzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]piperidin-1-yl]ethanone Chemical compound FC(F)C1=NC=2C(O)=CC=CC=2N1C(N=1)=NC(C2CCN(CC2)C(=O)CCl)=NC=1N1CCOCC1 ASTLEWBNLRJQNE-UHFFFAOYSA-N 0.000 claims 1
- GJKRWQWQISVTQV-UHFFFAOYSA-N 2-chloro-1-[4-[4-[2-(difluoromethyl)-4-hydroxybenzimidazol-1-yl]-6-pyridin-4-yl-1,3,5-triazin-2-yl]piperazin-1-yl]ethanone Chemical compound FC(F)C1=NC=2C(O)=CC=CC=2N1C(N=1)=NC(N2CCN(CC2)C(=O)CCl)=NC=1C1=CC=NC=C1 GJKRWQWQISVTQV-UHFFFAOYSA-N 0.000 claims 1
- IWNARFWONWBMKS-UHFFFAOYSA-N 2-chloro-1-[4-[4-[2-(difluoromethyl)-4-methoxybenzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]piperazin-1-yl]ethanone Chemical compound FC(F)C1=NC=2C(OC)=CC=CC=2N1C(N=1)=NC(N2CCOCC2)=NC=1N1CCN(C(=O)CCl)CC1 IWNARFWONWBMKS-UHFFFAOYSA-N 0.000 claims 1
- CMZZOPPGQGMPJV-UHFFFAOYSA-N 2-chloro-1-[4-[4-[2-(difluoromethyl)-4-methoxybenzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]piperazin-1-yl]propan-1-one Chemical compound FC(F)C1=NC=2C(OC)=CC=CC=2N1C(N=1)=NC(N2CCOCC2)=NC=1N1CCN(C(=O)C(C)Cl)CC1 CMZZOPPGQGMPJV-UHFFFAOYSA-N 0.000 claims 1
- JMECLBWPUPUUTM-UHFFFAOYSA-N 2-chloro-1-[4-[4-[2-(difluoromethyl)-4-methoxybenzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]piperidin-1-yl]ethanone Chemical compound FC(F)C1=NC=2C(OC)=CC=CC=2N1C(N=1)=NC(C2CCN(CC2)C(=O)CCl)=NC=1N1CCOCC1 JMECLBWPUPUUTM-UHFFFAOYSA-N 0.000 claims 1
- QMZAEEDKGAKPCW-UHFFFAOYSA-N 2-chloro-1-[4-[4-[2-(difluoromethyl)-4-methoxybenzimidazol-1-yl]-6-pyridin-4-yl-1,3,5-triazin-2-yl]piperazin-1-yl]ethanone Chemical compound FC(F)C1=NC=2C(OC)=CC=CC=2N1C(N=1)=NC(N2CCN(CC2)C(=O)CCl)=NC=1C1=CC=NC=C1 QMZAEEDKGAKPCW-UHFFFAOYSA-N 0.000 claims 1
- KHMXRDQDFBYNSH-UHFFFAOYSA-N 2-chloro-1-[4-[4-[2-(difluoromethyl)benzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]piperazin-1-yl]ethanone Chemical compound FC(F)C1=NC2=CC=CC=C2N1C(N=1)=NC(N2CCOCC2)=NC=1N1CCN(C(=O)CCl)CC1 KHMXRDQDFBYNSH-UHFFFAOYSA-N 0.000 claims 1
- NEVBIZOZXWSJNB-UHFFFAOYSA-N 2-chloro-1-[4-[4-[2-(difluoromethyl)benzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]piperidin-1-yl]ethanone Chemical compound FC(F)C1=NC2=CC=CC=C2N1C(N=1)=NC(C2CCN(CC2)C(=O)CCl)=NC=1N1CCOCC1 NEVBIZOZXWSJNB-UHFFFAOYSA-N 0.000 claims 1
- IEPGTHZLNFULRN-UHFFFAOYSA-N 2-chloro-1-[4-[4-[2-(difluoromethyl)benzimidazol-1-yl]-6-pyridin-4-yl-1,3,5-triazin-2-yl]piperazin-1-yl]ethanone Chemical compound FC(F)C1=NC2=CC=CC=C2N1C(N=1)=NC(N2CCN(CC2)C(=O)CCl)=NC=1C1=CC=NC=C1 IEPGTHZLNFULRN-UHFFFAOYSA-N 0.000 claims 1
- IAOWQVXUCSALQR-UHFFFAOYSA-N 2-chloro-1-[4-[4-[3-(hydroxymethyl)phenyl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]piperazin-1-yl]ethanone Chemical compound OCC1=CC=CC(C=2N=C(N=C(N=2)N2CCOCC2)N2CCN(CC2)C(=O)CCl)=C1 IAOWQVXUCSALQR-UHFFFAOYSA-N 0.000 claims 1
- BSAYQQGQUQTDMI-UHFFFAOYSA-N 2-chloro-1-[4-[4-[3-(hydroxymethyl)phenyl]-6-pyridin-4-yl-1,3,5-triazin-2-yl]piperazin-1-yl]ethanone Chemical compound OCC1=CC=CC(C=2N=C(N=C(N=2)N2CCN(CC2)C(=O)CCl)C=2C=CN=CC=2)=C1 BSAYQQGQUQTDMI-UHFFFAOYSA-N 0.000 claims 1
- HZRNSPCMNNVYDW-UHFFFAOYSA-N 2-chloro-1-[4-[[4-[2-(difluoromethyl)-4-[3-(dimethylamino)propoxy]benzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]-methylamino]piperidin-1-yl]ethanone Chemical compound FC(F)C1=NC=2C(OCCCN(C)C)=CC=CC=2N1C(N=1)=NC(N(C)C2CCN(CC2)C(=O)CCl)=NC=1N1CCOCC1 HZRNSPCMNNVYDW-UHFFFAOYSA-N 0.000 claims 1
- BJAYOLPEZVHSLS-UHFFFAOYSA-N 2-chloro-1-[4-[[4-[2-(difluoromethyl)-4-[3-(dimethylamino)propoxy]benzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]oxy]piperidin-1-yl]ethanone Chemical compound FC(F)C1=NC=2C(OCCCN(C)C)=CC=CC=2N1C(N=C(N=1)N2CCOCC2)=NC=1OC1CCN(C(=O)CCl)CC1 BJAYOLPEZVHSLS-UHFFFAOYSA-N 0.000 claims 1
- NNTHRMICRYVDHU-UHFFFAOYSA-N 2-chloro-1-[4-[[4-[2-(difluoromethyl)-4-ethoxybenzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]amino]piperidin-1-yl]ethanone Chemical compound FC(F)C1=NC=2C(OCC)=CC=CC=2N1C(N=C(N=1)N2CCOCC2)=NC=1NC1CCN(C(=O)CCl)CC1 NNTHRMICRYVDHU-UHFFFAOYSA-N 0.000 claims 1
- LRCBDVDTAQXAGK-UHFFFAOYSA-N 2-chloro-1-[4-[[4-[2-(difluoromethyl)-4-ethoxybenzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]oxy]piperidin-1-yl]ethanone Chemical compound FC(F)C1=NC=2C(OCC)=CC=CC=2N1C(N=C(N=1)N2CCOCC2)=NC=1OC1CCN(C(=O)CCl)CC1 LRCBDVDTAQXAGK-UHFFFAOYSA-N 0.000 claims 1
- HYXCVABMVKHIFU-UHFFFAOYSA-N 2-chloro-1-[4-[[4-[2-(difluoromethyl)-4-ethoxybenzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]sulfanyl]piperidin-1-yl]ethanone Chemical compound FC(F)C1=NC=2C(OCC)=CC=CC=2N1C(N=C(N=1)N2CCOCC2)=NC=1SC1CCN(C(=O)CCl)CC1 HYXCVABMVKHIFU-UHFFFAOYSA-N 0.000 claims 1
- YUYDCDNKFLONHQ-UHFFFAOYSA-N 2-chloro-1-[4-[[4-[2-(difluoromethyl)-4-hydroxybenzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]amino]piperidin-1-yl]ethanone Chemical compound FC(F)C1=NC=2C(O)=CC=CC=2N1C(N=C(N=1)N2CCOCC2)=NC=1NC1CCN(C(=O)CCl)CC1 YUYDCDNKFLONHQ-UHFFFAOYSA-N 0.000 claims 1
- MWNAUJJGVXRPSG-UHFFFAOYSA-N 2-chloro-1-[4-[[4-[2-(difluoromethyl)-4-hydroxybenzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]oxy]piperidin-1-yl]ethanone Chemical compound FC(F)C1=NC=2C(O)=CC=CC=2N1C(N=C(N=1)N2CCOCC2)=NC=1OC1CCN(C(=O)CCl)CC1 MWNAUJJGVXRPSG-UHFFFAOYSA-N 0.000 claims 1
- GVYXSNQIENQZFV-UHFFFAOYSA-N 2-chloro-1-[4-[[4-[2-(difluoromethyl)-4-hydroxybenzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]sulfanyl]piperidin-1-yl]ethanone Chemical compound FC(F)C1=NC=2C(O)=CC=CC=2N1C(N=C(N=1)N2CCOCC2)=NC=1SC1CCN(C(=O)CCl)CC1 GVYXSNQIENQZFV-UHFFFAOYSA-N 0.000 claims 1
- CSICSMWCXFHVKK-UHFFFAOYSA-N 2-chloro-1-[4-[[4-[2-(difluoromethyl)-4-methoxybenzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]-methylamino]piperidin-1-yl]ethanone Chemical compound FC(F)C1=NC=2C(OC)=CC=CC=2N1C(N=1)=NC(N(C)C2CCN(CC2)C(=O)CCl)=NC=1N1CCOCC1 CSICSMWCXFHVKK-UHFFFAOYSA-N 0.000 claims 1
- YNQOFUZDWZHACO-UHFFFAOYSA-N 2-chloro-1-[4-[[4-[2-(difluoromethyl)-4-methoxybenzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]amino]piperidin-1-yl]ethanone Chemical compound FC(F)C1=NC=2C(OC)=CC=CC=2N1C(N=C(N=1)N2CCOCC2)=NC=1NC1CCN(C(=O)CCl)CC1 YNQOFUZDWZHACO-UHFFFAOYSA-N 0.000 claims 1
- FSUBAMNDPWSDIV-UHFFFAOYSA-N 2-chloro-1-[4-[[4-[2-(difluoromethyl)-4-methoxybenzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]oxy]piperidin-1-yl]ethanone Chemical compound FC(F)C1=NC=2C(OC)=CC=CC=2N1C(N=C(N=1)N2CCOCC2)=NC=1OC1CCN(C(=O)CCl)CC1 FSUBAMNDPWSDIV-UHFFFAOYSA-N 0.000 claims 1
- QRVYVXUHSGIUEZ-UHFFFAOYSA-N 2-chloro-1-[4-[[4-[2-(difluoromethyl)-4-methoxybenzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]sulfanyl]piperidin-1-yl]ethanone Chemical compound FC(F)C1=NC=2C(OC)=CC=CC=2N1C(N=C(N=1)N2CCOCC2)=NC=1SC1CCN(C(=O)CCl)CC1 QRVYVXUHSGIUEZ-UHFFFAOYSA-N 0.000 claims 1
- MNCSXHRJHLLTRA-UHFFFAOYSA-N 2-chloro-1-[4-[[4-[2-(difluoromethyl)benzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]amino]piperidin-1-yl]ethanone Chemical compound FC(F)C1=NC2=CC=CC=C2N1C(N=C(N=1)N2CCOCC2)=NC=1NC1CCN(C(=O)CCl)CC1 MNCSXHRJHLLTRA-UHFFFAOYSA-N 0.000 claims 1
- IJGYXSYURNITFC-UHFFFAOYSA-N 2-chloro-1-[4-[[4-[2-(difluoromethyl)benzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]oxy]piperidin-1-yl]ethanone Chemical compound FC(F)C1=NC2=CC=CC=C2N1C(N=C(N=1)N2CCOCC2)=NC=1OC1CCN(C(=O)CCl)CC1 IJGYXSYURNITFC-UHFFFAOYSA-N 0.000 claims 1
- UFLKYTBJELJXNA-UHFFFAOYSA-N 2-chloro-1-[4-[[4-[2-(difluoromethyl)benzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]sulfanyl]piperidin-1-yl]ethanone Chemical compound FC(F)C1=NC2=CC=CC=C2N1C(N=C(N=1)N2CCOCC2)=NC=1SC1CCN(C(=O)CCl)CC1 UFLKYTBJELJXNA-UHFFFAOYSA-N 0.000 claims 1
- WFGXGZFUBZKGDT-UHFFFAOYSA-N 2-chloro-n-[1-[4-[2-(difluoromethyl)-4-methoxybenzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]azetidin-3-yl]-n-methylacetamide Chemical compound FC(F)C1=NC=2C(OC)=CC=CC=2N1C(N=1)=NC(N2CC(C2)N(C)C(=O)CCl)=NC=1N1CCOCC1 WFGXGZFUBZKGDT-UHFFFAOYSA-N 0.000 claims 1
- FJILIOHMVAFTDV-UHFFFAOYSA-N 2-chloro-n-[1-[4-[2-(difluoromethyl)-4-methoxybenzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]piperidin-4-yl]-n-methylacetamide Chemical compound FC(F)C1=NC=2C(OC)=CC=CC=2N1C(N=1)=NC(N2CCOCC2)=NC=1N1CCC(N(C)C(=O)CCl)CC1 FJILIOHMVAFTDV-UHFFFAOYSA-N 0.000 claims 1
- DXXWJNJCSUHILR-UHFFFAOYSA-N 3-[1-[4-[4-(chloromethylsulfonyl)piperazin-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]-2-(difluoromethyl)benzimidazol-4-yl]oxy-n,n-dimethylpropan-1-amine Chemical compound FC(F)C1=NC=2C(OCCCN(C)C)=CC=CC=2N1C(N=1)=NC(N2CCOCC2)=NC=1N1CCN(S(=O)(=O)CCl)CC1 DXXWJNJCSUHILR-UHFFFAOYSA-N 0.000 claims 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 1
- ZQTSFAONGDKHCD-UHFFFAOYSA-N 4-[1-[1-(chloromethylsulfonyl)piperidin-4-yl]-6-[2-(difluoromethyl)-4-methoxybenzimidazol-1-yl]pyrazolo[3,4-d]pyrimidin-4-yl]morpholine Chemical compound FC(F)C1=NC=2C(OC)=CC=CC=2N1C(N=C1N(C2CCN(CC2)S(=O)(=O)CCl)N=CC1=1)=NC=1N1CCOCC1 ZQTSFAONGDKHCD-UHFFFAOYSA-N 0.000 claims 1
- AILLDYHYJOFYDK-UHFFFAOYSA-N 4-[2-[4-(chloromethylsulfonyl)piperazin-1-yl]-6-[2-(difluoromethyl)-4-methoxybenzimidazol-1-yl]pyrimidin-4-yl]morpholine Chemical compound FC(F)C1=NC=2C(OC)=CC=CC=2N1C(N=1)=CC(N2CCOCC2)=NC=1N1CCN(S(=O)(=O)CCl)CC1 AILLDYHYJOFYDK-UHFFFAOYSA-N 0.000 claims 1
- WYCPOEIUUCAPMV-UHFFFAOYSA-N 4-[4-[4-(bromomethylsulfonyl)piperazin-1-yl]-6-[2-(difluoromethyl)-4-methoxybenzimidazol-1-yl]-1,3,5-triazin-2-yl]morpholine Chemical compound FC(F)C1=NC=2C(OC)=CC=CC=2N1C(N=1)=NC(N2CCOCC2)=NC=1N1CCN(S(=O)(=O)CBr)CC1 WYCPOEIUUCAPMV-UHFFFAOYSA-N 0.000 claims 1
- FSFGWLJCEFUATQ-UHFFFAOYSA-N 4-[4-[4-(chloromethylsulfonyl)piperazin-1-yl]-6-[2-(difluoromethyl)-4-methoxybenzimidazol-1-yl]-1,3,5-triazin-2-yl]morpholine Chemical compound FC(F)C1=NC=2C(OC)=CC=CC=2N1C(N=1)=NC(N2CCOCC2)=NC=1N1CCN(S(=O)(=O)CCl)CC1 FSFGWLJCEFUATQ-UHFFFAOYSA-N 0.000 claims 1
- DDGXHRREFJTKDQ-UHFFFAOYSA-N 4-[4-[4-(chloromethylsulfonyl)piperazin-1-yl]-6-[2-(difluoromethyl)-4-methoxybenzimidazol-1-yl]pyrimidin-2-yl]morpholine Chemical compound FC(F)C1=NC=2C(OC)=CC=CC=2N1C(N=1)=CC(N2CCN(CC2)S(=O)(=O)CCl)=NC=1N1CCOCC1 DDGXHRREFJTKDQ-UHFFFAOYSA-N 0.000 claims 1
- HJGPEOFMUDMIRJ-UHFFFAOYSA-N 4-[6-[4-(chloromethylsulfonyl)piperazin-1-yl]-2-[2-(difluoromethyl)-4-methoxybenzimidazol-1-yl]pyrimidin-4-yl]morpholine Chemical compound FC(F)C1=NC=2C(OC)=CC=CC=2N1C(N=1)=NC(N2CCOCC2)=CC=1N1CCN(S(=O)(=O)CCl)CC1 HJGPEOFMUDMIRJ-UHFFFAOYSA-N 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- SOWBFZRMHSNYGE-UHFFFAOYSA-N Monoamide-Oxalic acid Natural products NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- UPCVEYWTLBPVMH-UHFFFAOYSA-N [2-[4-[4-[2-(difluoromethyl)-4-methoxybenzimidazol-1-yl]-6-morpholin-4-yl-1,3,5-triazin-2-yl]piperazin-1-yl]-2-oxoethyl] methanesulfonate Chemical compound FC(F)C1=NC=2C(OC)=CC=CC=2N1C(N=1)=NC(N2CCOCC2)=NC=1N1CCN(C(=O)COS(C)(=O)=O)CC1 UPCVEYWTLBPVMH-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 239000006207 intravenous dosage form Substances 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- IHAVJVYHVXTMCI-UHFFFAOYSA-N n-[1-(chloromethylsulfonyl)piperidin-4-yl]-4-[2-(difluoromethyl)-4-methoxybenzimidazol-1-yl]-n-methyl-6-morpholin-4-yl-1,3,5-triazin-2-amine Chemical compound FC(F)C1=NC=2C(OC)=CC=CC=2N1C(N=1)=NC(N(C)C2CCN(CC2)S(=O)(=O)CCl)=NC=1N1CCOCC1 IHAVJVYHVXTMCI-UHFFFAOYSA-N 0.000 claims 1
- 239000006201 parenteral dosage form Substances 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4006408P | 2008-03-27 | 2008-03-27 | |
| US61/040,064 | 2008-03-27 | ||
| PCT/NZ2009/000038 WO2009120094A2 (en) | 2008-03-27 | 2009-03-26 | Substituted pyrimidines and triazines and their use in cancer therapy |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011515462A JP2011515462A (ja) | 2011-05-19 |
| JP2011515462A5 true JP2011515462A5 (enExample) | 2012-05-17 |
Family
ID=40810252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011501736A Abandoned JP2011515462A (ja) | 2008-03-27 | 2009-03-26 | 置換されたピリミジン、及びトリアジン、並びに癌療法におけるこれらの使用 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US20110053907A1 (enExample) |
| EP (1) | EP2276750A2 (enExample) |
| JP (1) | JP2011515462A (enExample) |
| WO (1) | WO2009120094A2 (enExample) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008128088A1 (en) | 2007-04-13 | 2008-10-23 | The Regents Of The University Of Michigan | Systems and methods for tissue imaging |
| EP2282672A4 (en) * | 2008-02-29 | 2013-03-20 | Univ Michigan | SYSTEMS AND METHOD FOR ILLUSTRATING TISSUE CHANGES |
| US20120165309A1 (en) * | 2009-02-12 | 2012-06-28 | Astellas Pharma Inc. | Hetero ring derivative |
| MX2011009796A (es) | 2009-03-20 | 2011-12-14 | Amgen Inc | Inhibidores de la cinasa pi3. |
| WO2010110686A1 (en) * | 2009-03-27 | 2010-09-30 | Pathway Therapeutics Limited | Pyrimidinyl and 1,3,5 triazinyl benzimidazoles and their use in cancer therapy |
| TW201038567A (en) * | 2009-03-27 | 2010-11-01 | Pathway Therapeutics Ltd | Pyrimidinyl and 1,3,5-triazinyl benzimidazole sulfonamides and their use in cancer therapy |
| UY32582A (es) | 2009-04-28 | 2010-11-30 | Amgen Inc | Inhibidores de fosfoinositida 3 cinasa y/u objetivo mamífero |
| TW201105662A (en) | 2009-07-07 | 2011-02-16 | Pathway Therapeutics Ltd | Pyrimidinyl and 1,3,5-triazinyl benzimidazoles and their use in cancer therapy |
| CA2775942A1 (en) * | 2009-09-29 | 2011-04-07 | Xcovery Holding Company Llc | Pi3k (delta) selective inhibitors |
| WO2011049625A1 (en) | 2009-10-20 | 2011-04-28 | Mansour Samadpour | Method for aflatoxin screening of products |
| JP5889795B2 (ja) | 2009-11-05 | 2016-03-22 | ライゼン・ファーマシューティカルズ・エスアー | 新規キナーゼモジュレーター |
| GB201007227D0 (en) * | 2010-04-30 | 2010-06-16 | Univ Basel | Piperazinotriazines |
| EP2604601B1 (en) * | 2010-08-10 | 2016-02-24 | Astellas Pharma Inc. | Hetero ring compound |
| WO2012044641A1 (en) | 2010-09-29 | 2012-04-05 | Pathway Therapeutics Inc. | 1,3,5-triazinyl benzimidazole sulfonamides and their use in cancer therapy |
| CZ305457B6 (cs) | 2011-02-28 | 2015-09-30 | Ústav organické chemie a biochemie, Akademie věd ČR v. v. i. | Pyrimidinové sloučeniny inhibující tvorbu oxidu dusnatého a prostaglandinu E2, způsob výroby a použití |
| AU2012236834B2 (en) | 2011-03-28 | 2015-12-10 | Mei Pharma, Inc | (alpha- substituted aralkylamino and heteroarylalkylamino) pyrimidinyl and 1,3,5 -triazinyl benzimidazoles, pharmaceutical compositions containing them, and these compounds for use in treating proliferative diseases |
| PH12013502240B1 (en) | 2011-05-04 | 2018-06-27 | Rhizen Pharmaceuticals Sa | Novel compounds as modulators of protein kinase |
| US9773311B2 (en) | 2011-06-29 | 2017-09-26 | The Regents Of The University Of Michigan | Tissue phasic classification mapping system and method |
| JP6026544B2 (ja) | 2011-09-27 | 2016-11-16 | ノバルティス アーゲー | 変異体ｉｄｈの阻害剤としての３−ピリミジン−４−イル−オキサゾリジン−２−オン類 |
| CA2851082A1 (en) * | 2011-10-06 | 2013-04-11 | Merck Sharp & Dohme Corp. | 1,3-substituted azetidine pde10 inhibitors |
| WO2013078370A1 (en) | 2011-11-23 | 2013-05-30 | The Regents Of The University Of Michigan | Voxel-based approach for disease detection and evolution |
| PL2790705T3 (pl) | 2011-12-15 | 2018-06-29 | Novartis Ag | Zastosowanie inhibitorów czynności lub funkcji PI3K |
| UY34632A (es) | 2012-02-24 | 2013-05-31 | Novartis Ag | Compuestos de oxazolidin- 2- ona y usos de los mismos |
| US9851426B2 (en) | 2012-05-04 | 2017-12-26 | The Regents Of The University Of Michigan | Error analysis and correction of MRI ADC measurements for gradient nonlinearity |
| KR102216606B1 (ko) | 2012-07-04 | 2021-02-17 | 리젠 파마슈티컬스 소시에떼 아노님 | 선택적 pi3k 델타 억제제 |
| WO2014055647A1 (en) * | 2012-10-03 | 2014-04-10 | Mei Pharma, Inc. | (sulfinyl and sulfonyl benzimidazolyl) pyrimidines and triazines, pharmaceutical compositions thereof, and their use for treating proliferative diseases |
| US9296733B2 (en) | 2012-11-12 | 2016-03-29 | Novartis Ag | Oxazolidin-2-one-pyrimidine derivative and use thereof for the treatment of conditions, diseases and disorders dependent upon PI3 kinases |
| EP2968345B1 (en) | 2013-03-13 | 2017-12-13 | The Regents of The University of Michigan | Dual mek/pi3k inhibitors and their application in the treatment of cancer diseases |
| GEP201706699B (en) | 2013-03-14 | 2017-07-10 | Novartis Ag | 3-pyrimidin-4-yl-oxazolidin-2-ones as inhibitors of mutant idh |
| CA3026149A1 (en) | 2016-06-02 | 2017-12-07 | Cadent Therapeutics, Inc. | Potassium channel modulators |
| US10650512B2 (en) | 2016-06-14 | 2020-05-12 | The Regents Of The University Of Michigan | Systems and methods for topographical characterization of medical image data |
| JP2019519593A (ja) | 2016-07-06 | 2019-07-11 | ザ・リージェンツ・オブ・ザ・ユニバーシティ・オブ・ミシガンＴｈｅ Ｒｅｇｅｎｔｓ Ｏｆ Ｔｈｅ Ｕｎｉｖｅｒｓｉｔｙ Ｏｆ Ｍｉｃｈｉｇａｎ | ＭＥＫ／ＰＩ３Ｋ及びｍＴＯＲ／ＭＥＫ／ＰＩ３Ｋ生物学的経路の多官能性阻害剤、並びに同多官能性阻害剤を用いた治療方法 |
| BR112019014814B1 (pt) | 2017-01-23 | 2024-03-12 | Novartis Ag | Compostos, composições farmacêuticas dos mesmos e seus usos no tratamento de doenças associadas à disfunção de canais iônicos de potássio |
| CN117860758A (zh) | 2017-05-23 | 2024-04-12 | 梅制药公司 | 联合疗法 |
| US11311624B2 (en) | 2017-08-11 | 2022-04-26 | The Regents Of The University Of Michigan | Inhibitors of MEK/PI3K, JAK/MEK, JAK/PI3K/mTOR and MEK/PI3K/mTOR biological pathways and methods for improving lymphatic uptake, bioavailability, and solubility of therapeutic compounds |
| MX2020001727A (es) | 2017-08-14 | 2020-03-20 | Mei Pharma Inc | Terapia de combinacion. |
| WO2019119206A1 (en) * | 2017-12-18 | 2019-06-27 | Merck Sharp & Dohme Corp. | Purine inhibitors of human phosphatidylinositol 3-kinase delta |
| CA3116339A1 (en) | 2018-10-22 | 2020-04-30 | Cadent Therapeutics, Inc. | Crystalline forms of potassium channel modulators |
| CN113004246B (zh) * | 2021-02-22 | 2022-02-01 | 广西医科大学 | 1，3，5-三嗪-2-胺-4，6取代衍生物或其药学上可接受的盐和用途 |
| EP4320110A1 (en) * | 2021-04-09 | 2024-02-14 | Universität Basel | Triazine derivative as covalent inhibitors of pi3k |
| CN117751127A (zh) * | 2021-08-20 | 2024-03-22 | 南京大美生物制药有限公司 | 一种五元含氮杂环并杂芳基类衍生物及其用途 |
Family Cites Families (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1222049B (it) * | 1987-07-16 | 1990-08-31 | Ciba Geygi Spa | Composti piperidin triazinici utilizzabili come stabilizzanti per polimeri sintetici |
| US5244948A (en) * | 1988-06-30 | 1993-09-14 | Ciba-Geigy Corporation | Process for the stabilization of polyolefins |
| US5306495A (en) * | 1988-08-04 | 1994-04-26 | Ciba-Geigy Corporation | Compounds containing substituted piperidine groups for use as stabilizers for organic materials |
| IT1237126B (it) * | 1989-11-07 | 1993-05-18 | Ciba Geigy Spa | Stabilizzanti polimerici contenenti gruppi amminici impediti e gruppi idrossilamminici |
| US5258138A (en) * | 1990-07-20 | 1993-11-02 | Ciba-Geigy Corporation | Process for stabilizing ethylenically unsaturated compounds and stabilized monomer compositions |
| TW224983B (enExample) * | 1991-08-28 | 1994-06-11 | Hoechst Ag | |
| AU665238B2 (en) * | 1992-02-28 | 1995-12-21 | Zenyaku Kogyo Kabushiki Kaisha | S-triazine derivative and remedy for estrogen-dependent diseases containing the same as active ingredient |
| HU209678B (en) * | 1992-06-09 | 1994-10-28 | Richter Gedeon Vegyeszet | Process for producing biologically active eburnamenin-14-carbonyl-amino derivatives and pharmaceutical compositions containing them |
| IT1263993B (it) * | 1993-04-05 | 1996-09-06 | Ciba Geigy Spa | Composti piperidin-triazinici atti all'impiego come stabilizzanti per materiali organici |
| IT1270975B (it) * | 1993-06-03 | 1997-05-26 | Ciba Geigy Spa | Composti piperidin-triazinici atti all'impiego come stabilizzanti allaluce, al calore e alla ossidazione per materiali organici |
| ATE180283T1 (de) * | 1994-01-19 | 1999-06-15 | Ciba Geigy Ag | Stabilisieren von leder gegen thermische und photochemische zersetzung |
| EP0707035B1 (de) * | 1994-10-12 | 1999-01-13 | Ciba SC Holding AG | HALS-Phosphorinane als Stabilisatoren |
| EP0711804A3 (de) * | 1994-11-14 | 1999-09-22 | Ciba SC Holding AG | Kryptolichtschutzmittel |
| DE19522137A1 (de) * | 1995-06-19 | 1997-01-02 | Hoechst Schering Agrevo Gmbh | 2-Amino-1,3,5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| JP3512911B2 (ja) * | 1995-07-11 | 2004-03-31 | 富士写真フイルム株式会社 | 紫外線吸収剤前駆体化合物、それを含有する感光性樹脂組成物及び画像形成方法 |
| US6046304A (en) * | 1995-12-04 | 2000-04-04 | Ciba Specialty Chemicals Corporation | Block oligomers containing 2,2,6,6-tetramethyl-4-piperidyl groups as stabilizers for organic materials |
| US6432947B1 (en) * | 1997-02-19 | 2002-08-13 | Berlex Laboratories, Inc. | N-heterocyclic derivatives as NOS inhibitors |
| DE69821633T2 (de) * | 1997-07-24 | 2004-12-16 | Zenyaku Kogyo K.K. | Heterozyklische verbindungen und antitumormittel, das diese als aktiven wirkstoff enthält |
| JPH11174638A (ja) * | 1997-12-08 | 1999-07-02 | Konica Corp | ハロゲン化銀カラー写真感光材料 |
| US6150362A (en) * | 1997-12-12 | 2000-11-21 | Henkin; Jack | Triazine angiogenesis inhibitors |
| US5990208A (en) * | 1997-12-15 | 1999-11-23 | Ciba Specialty Chemicals Corporation | Stabilization of polycarbonate/ABS blends with mixtures of hindered amines and UV absorbers |
| CA2359678A1 (en) * | 1999-01-13 | 2000-07-20 | Miles Hacker | Use of s-triazines for treating apicomplexan parasitic infections |
| ATE361917T1 (de) * | 1999-04-22 | 2007-06-15 | Lundbeck & Co As H | Selektive npy(y5)-antagonisten |
| KR100551853B1 (ko) * | 2000-07-19 | 2006-02-13 | 에프. 호프만-라 로슈 아게 | 피리미딘 유도체 |
| US6465645B1 (en) * | 2001-04-17 | 2002-10-15 | Ciba Specialty Chemicals Corporation | Long chain hindered amines and compositions stabilized therewith |
| PT1389617E (pt) * | 2001-04-27 | 2007-04-30 | Zenyaku Kogyo Kk | Composto heterocíclico e agente antitumoral contendo o mesmo como igrediente activo |
| AU2003275630B2 (en) * | 2002-10-25 | 2010-02-18 | Zenyaku Kogyo Kabushiki Kaisha | Heterocyclic compounds and antitumor agent comprising the same as effective component |
| WO2005028467A1 (en) * | 2003-09-15 | 2005-03-31 | Anadys Pharmaceuticals, Inc. | Antibacterial 3,5-diaminopiperidine-substitute aromatic and heteroaromatic compounds |
| ES2400056T3 (es) * | 2004-03-31 | 2013-04-05 | Zenyaku Kogyo Kabushikikaisha | Compuesto heterocíclico y agente anti tumores malignos que comprende el mismo como componente eficaz |
| EP1824490A4 (en) * | 2004-12-13 | 2008-06-04 | Neurogen Corp | PIPERAZINYL-PYRIDINE ANALOGS |
| CA2590586A1 (en) * | 2004-12-13 | 2006-07-06 | Neurogen Corporation | Substituted biaryl analogues |
| GB0503962D0 (en) * | 2005-02-25 | 2005-04-06 | Kudos Pharm Ltd | Compounds |
| TWI381841B (zh) * | 2005-03-11 | 2013-01-11 | Zenyaku Kogyo Kk | An immunosuppressive agent and an antitumor agent containing a heterocyclic compound as an active ingredient |
| ES2401192T3 (es) * | 2005-09-30 | 2013-04-17 | Vertex Pharmceuticals Incorporated | Deazapurinas útiles como inhibidores de janus cinasas |
| JO2660B1 (en) * | 2006-01-20 | 2012-06-17 | نوفارتيس ايه جي | Pi-3 inhibitors and methods of use |
| US20070244110A1 (en) * | 2006-04-14 | 2007-10-18 | Zenyaku Kogyo Kabushiki Kaisha | Treatment of prostate cancer, melanoma or hepatic cancer |
| WO2007127175A2 (en) * | 2006-04-26 | 2007-11-08 | F. Hoffmann-La Roche Ag | Pharmaceutical compounds |
| WO2008032072A1 (en) * | 2006-09-14 | 2008-03-20 | Astrazeneca Ab | 2-benzimidaz0lyl-6-m0rph0lin0-4-piperidin-4-ylpyrimidine derivatives as pi3k and mtor inhibitors for the treatment of proliferative disorders |
| US20090325954A1 (en) * | 2006-09-14 | 2009-12-31 | Sam Butterworth | 2-benzimidazolyl-6-morpholino-4-phenylpyrimidine derivatives as pi3k and mtor inhibitors for the treatment of proliferative disorders |
| JP2010503649A (ja) * | 2006-09-14 | 2010-02-04 | アストラゼネカ アクチボラグ | ピリミジン誘導体 |
| WO2008032028A1 (en) * | 2006-09-14 | 2008-03-20 | Astrazeneca Ab | 2 -benzimidazolyl- 6 -morpholino-4- (azetidine, pyrrolidine, piperidine or azepine) pyrimidine derivatives as pi3k and mtor inhibitors for the treatment of proliferative disorders |
| WO2008072850A1 (en) * | 2006-12-11 | 2008-06-19 | Amorepacific Corporation | Triazine derivatives having inhibitory activity against acetyl-coa carboxylase |
| EA201001017A1 (ru) * | 2008-01-15 | 2011-02-28 | ВАЙЕТ ЭлЭлСи | 3h-[1,2,3]триазоло[4,5-d]пиримидиновые соединения, их применение в качестве ингибиторов киназы mtor и киназы pi3 и их синтезы |
| US20090192176A1 (en) * | 2008-01-30 | 2009-07-30 | Wyeth | 1H-PYRAZOLO[3,4-D]PYRIMIDINE, PURINE, 7H-PURIN-8(9H)-ONE, 3H-[1,2,3]TRIAZOLO[4,5-D]PYRIMIDINE, AND THIENO[3,2-D]PYRIMIDINE COMPOUNDS, THEIR USE AS mTOR KINASE AND PI3 KINASE INHIBITORS, AND THEIR SYNTHESES |
-
2009
- 2009-03-26 EP EP09724191A patent/EP2276750A2/en not_active Withdrawn
- 2009-03-26 JP JP2011501736A patent/JP2011515462A/ja not_active Abandoned
- 2009-03-26 WO PCT/NZ2009/000038 patent/WO2009120094A2/en not_active Ceased
- 2009-03-26 US US12/934,616 patent/US20110053907A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2011515462A5 (enExample) | ||
| US10576080B2 (en) | Compounds and compositions as protein kinase inhibitors | |
| RU2011143359A (ru) | Примидинил- и 1,3,5-триазинилбензимидазолсульфонамиды и их применение в терапии рака | |
| CN106170288B (zh) | 药物化合物 | |
| JP2008517926A5 (enExample) | ||
| JP2005533803A5 (enExample) | ||
| JP5938038B2 (ja) | ピラゾロフェニル−ベンゼンスルホンアミド化合物の誘導体及びその抗腫瘍薬としての使用 | |
| JP2009541268A5 (enExample) | ||
| JP2009541311A5 (enExample) | ||
| JP2017510555A5 (enExample) | ||
| CA2984259A1 (en) | Combinations of inhibitors of irak4 with inhibitors of btk | |
| JP2005530722A5 (enExample) | ||
| HUE033177T2 (en) | Pyrazine carboxamide compound | |
| JP2004534010A5 (enExample) | ||
| JP2008513514A5 (enExample) | ||
| CA2585053A1 (en) | Substituted n-acyl (hetero)aryl compounds as c-fms kinase inhibitors | |
| RU2011127232A (ru) | Апоптоз-индуцирующие средства для лечения рака и иммунных и аутоиммунных заболеваний | |
| JP2014511869A5 (enExample) | ||
| CN114430740A (zh) | Egfr抑制剂、组合物及其制备方法 | |
| JP2014531436A5 (enExample) | ||
| AU2016317806A1 (en) | Heteroaryl compounds and their use as therapeutic drugs | |
| JP2006507247A5 (enExample) | ||
| EP3585365A1 (en) | Combination of atr kinase inhibitors with parp inhibitors | |
| JP2008513405A5 (enExample) | ||
| JP2025509895A (ja) | Ｔｅａドメインファミリーメンバーの小分子阻害薬 |