JP2016526561A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2016526561A5 JP2016526561A5 JP2016524672A JP2016524672A JP2016526561A5 JP 2016526561 A5 JP2016526561 A5 JP 2016526561A5 JP 2016524672 A JP2016524672 A JP 2016524672A JP 2016524672 A JP2016524672 A JP 2016524672A JP 2016526561 A5 JP2016526561 A5 JP 2016526561A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkylene
- nhch
- phenyl
- triazine
- 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
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 180
- 125000002947 alkylene group Chemical group 0.000 claims description 119
- UCDSGVJLGDUWQF-UHFFFAOYSA-N methyl 2-[[1-[4-(cyclopropylamino)-6-(ethylamino)-1,3,5-triazin-2-yl]-1,2,4-triazol-3-yl]sulfanyl]acetate Chemical compound N=1C(N2N=C(SCC(=O)OC)N=C2)=NC(NCC)=NC=1NC1CC1 UCDSGVJLGDUWQF-UHFFFAOYSA-N 0.000 claims description 119
- -1 2-aminoethoxy Chemical group 0.000 claims description 78
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 55
- 230000035772 mutation Effects 0.000 claims description 53
- 150000001875 compounds Chemical class 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- XCBWOFAJTBVSQW-UHFFFAOYSA-N n-[[4-[[[4-(cyclopropylamino)-6-pyridin-2-yl-1,3,5-triazin-2-yl]amino]methyl]cyclohexyl]methyl]-4-fluorobenzenesulfonamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)NCC1CCC(CNC=2N=C(N=C(NC3CC3)N=2)C=2N=CC=CC=2)CC1 XCBWOFAJTBVSQW-UHFFFAOYSA-N 0.000 claims description 37
- 229910052799 carbon Inorganic materials 0.000 claims description 34
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 29
- WJDUCVZJAKHDOA-UHFFFAOYSA-N 2-[[1-[4-(cyclopropylamino)-6-(ethylamino)-1,3,5-triazin-2-yl]-1,2,4-triazol-3-yl]sulfanyl]acetamide Chemical compound N=1C(N2N=C(SCC(N)=O)N=C2)=NC(NCC)=NC=1NC1CC1 WJDUCVZJAKHDOA-UHFFFAOYSA-N 0.000 claims description 28
- 206010028980 Neoplasm Diseases 0.000 claims description 26
- 201000011510 cancer Diseases 0.000 claims description 24
- 125000005843 halogen group Chemical group 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
- BADKRWJBDCZDGE-UHFFFAOYSA-N 2-chloro-n-[4-(cyclopropylamino)-6-pyridin-2-yl-1,3,5-triazin-2-yl]-4-methylsulfonylbenzamide Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)NC1=NC(NC2CC2)=NC(C=2N=CC=CC=2)=N1 BADKRWJBDCZDGE-UHFFFAOYSA-N 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 101001042041 Bos taurus Isocitrate dehydrogenase [NAD] subunit beta, mitochondrial Proteins 0.000 claims description 19
- 101000960234 Homo sapiens Isocitrate dehydrogenase [NADP] cytoplasmic Proteins 0.000 claims description 19
- 102100039905 Isocitrate dehydrogenase [NADP] cytoplasmic Human genes 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 125000004076 pyridyl group Chemical group 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 claims description 10
- 230000001419 dependent effect Effects 0.000 claims description 10
- 102000004190 Enzymes Human genes 0.000 claims description 9
- 108090000790 Enzymes Proteins 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
- 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001475 halogen functional group Chemical group 0.000 claims description 6
- MISVBCMQSJUHMH-UHFFFAOYSA-N pyrimidine-4,6-diamine Chemical compound NC1=CC(N)=NC=N1 MISVBCMQSJUHMH-UHFFFAOYSA-N 0.000 claims description 6
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 5
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 4
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- DAHUIPUHTPGWLB-UHFFFAOYSA-N 2-(oxan-4-ylimino)-6-phenyl-4-propan-2-yl-1,3-dihydro-1,3,5-triazin-4-amine Chemical compound C(C)(C)C1(NC(=NC(=N1)NC1CCOCC1)C1=CC=CC=C1)N DAHUIPUHTPGWLB-UHFFFAOYSA-N 0.000 claims description 4
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims description 4
- LITAUKSSPWVCRT-UHFFFAOYSA-N 4-[2-[[4-(5-aminopentylamino)-6-(3-fluorophenyl)-1,3,5-triazin-2-yl]amino]ethyl]phenol Chemical compound N=1C(C=2C=C(F)C=CC=2)=NC(NCCCCCN)=NC=1NCCC1=CC=C(O)C=C1 LITAUKSSPWVCRT-UHFFFAOYSA-N 0.000 claims description 4
- SLOLUFRSDBPPPI-UHFFFAOYSA-N 4-[2-[[4-(5-aminopentylamino)-6-(4-fluorophenyl)-1,3,5-triazin-2-yl]amino]ethyl]phenol Chemical compound N=1C(C=2C=CC(F)=CC=2)=NC(NCCCCCN)=NC=1NCCC1=CC=C(O)C=C1 SLOLUFRSDBPPPI-UHFFFAOYSA-N 0.000 claims description 4
- UQZXEHZIVCMLSE-UHFFFAOYSA-N COC1=CC=C(C=C1)CNC1=NC(=NC(=N1)NCC1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC(F)(F)F Chemical compound COC1=CC=C(C=C1)CNC1=NC(=NC(=N1)NCC1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC(F)(F)F UQZXEHZIVCMLSE-UHFFFAOYSA-N 0.000 claims description 4
- HHDURDUNUHMQJQ-UHFFFAOYSA-N Cc1ccc(NC(=O)Nc2ccc(Cl)c(c2)C(F)(F)F)cc1-c1nc(NCCCCN)nc(NCC(O)=O)n1 Chemical compound Cc1ccc(NC(=O)Nc2ccc(Cl)c(c2)C(F)(F)F)cc1-c1nc(NCCCCN)nc(NCC(O)=O)n1 HHDURDUNUHMQJQ-UHFFFAOYSA-N 0.000 claims description 4
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims description 4
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- LKSCULJAMHWSQK-UHFFFAOYSA-N n-[4-(4,6-diacetamido-1,3,5-triazin-2-yl)-1,2,5-oxadiazol-3-yl]acetamide Chemical compound CC(=O)NC1=NON=C1C1=NC(NC(C)=O)=NC(NC(C)=O)=N1 LKSCULJAMHWSQK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 4
- VMJOXGDGZFSOKX-UHFFFAOYSA-N O=C1C2CCCCC2C(=O)C2C(CCCC12)Nc1nc(NC2CCCC3C2C(=O)C2CCCCC2C3=O)nc(n1)-c1ccccc1 Chemical compound O=C1C2CCCCC2C(=O)C2C(CCCC12)Nc1nc(NC2CCCC3C2C(=O)C2CCCCC2C3=O)nc(n1)-c1ccccc1 VMJOXGDGZFSOKX-UHFFFAOYSA-N 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- JSEZODAYDINJHU-UHFFFAOYSA-N ethyl 2-[5-[4,6-bis(diethylamino)-1,3,5-triazin-2-yl]tetrazol-2-yl]acetate Chemical compound CCOC(=O)CN1N=NC(C=2N=C(N=C(N=2)N(CC)CC)N(CC)CC)=N1 JSEZODAYDINJHU-UHFFFAOYSA-N 0.000 claims description 3
- HNGGQDHOALRLAE-UHFFFAOYSA-N n-[4-(benzylamino)-6-pyridin-2-yl-1,3,5-triazin-2-yl]-2-chloro-4-methylsulfonylbenzamide Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)NC1=NC(NCC=2C=CC=CC=2)=NC(C=2N=CC=CC=2)=N1 HNGGQDHOALRLAE-UHFFFAOYSA-N 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 229940124597 therapeutic agent Drugs 0.000 claims description 3
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- XBCWOPHYAHRFCZ-UHFFFAOYSA-N 3-[[6-(2,3-dihydro-1h-inden-2-ylamino)-2-pyridin-2-ylpyrimidin-4-yl]amino]propanoic acid Chemical compound N=1C(NCCC(=O)O)=CC(NC2CC3=CC=CC=C3C2)=NC=1C1=CC=CC=N1 XBCWOPHYAHRFCZ-UHFFFAOYSA-N 0.000 claims description 2
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 2
- 125000006414 CCl Chemical group ClC* 0.000 claims description 2
- 208000005243 Chondrosarcoma Diseases 0.000 claims description 2
- 206010009944 Colon cancer Diseases 0.000 claims description 2
- 208000032612 Glial tumor Diseases 0.000 claims description 2
- 206010018338 Glioma Diseases 0.000 claims description 2
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 2
- 201000007224 Myeloproliferative neoplasm Diseases 0.000 claims description 2
- NMELLUXIHPTMON-UHFFFAOYSA-N OCCNc1cc(NC2CC3CCC2C3)nc(n1)-c1ccccc1 Chemical compound OCCNc1cc(NC2CC3CCC2C3)nc(n1)-c1ccccc1 NMELLUXIHPTMON-UHFFFAOYSA-N 0.000 claims description 2
- 206010039491 Sarcoma Diseases 0.000 claims description 2
- 125000002393 azetidinyl group Chemical group 0.000 claims description 2
- 208000006990 cholangiocarcinoma Diseases 0.000 claims description 2
- 208000029742 colonic neoplasm Diseases 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 208000005017 glioblastoma Diseases 0.000 claims description 2
- 201000001441 melanoma Diseases 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- AERQMVYPVMXKOC-UHFFFAOYSA-N 6-(3-benzylsulfanyl-1,2,4-triazol-1-yl)-4-cyclopropyl-2-ethylimino-1,3-dihydro-1,3,5-triazin-4-amine Chemical compound C1(CC1)C1(NC(=NC(=N1)NCC)N1N=C(N=C1)SCC1=CC=CC=C1)N AERQMVYPVMXKOC-UHFFFAOYSA-N 0.000 claims 26
- LJVPQCPZMSVWLX-UHFFFAOYSA-N 4-cyclohexyl-2-cyclohexylimino-6-[3-(4-methoxyphenyl)-5-methylsulfanylpyrazol-1-yl]-1,3-dihydro-1,3,5-triazin-4-amine Chemical compound C1(CCCCC1)C1(NC(=NC(=N1)NC1CCCCC1)N1N=C(C=C1SC)C1=CC=C(C=C1)OC)N LJVPQCPZMSVWLX-UHFFFAOYSA-N 0.000 claims 22
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 9
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 6
- CZTUKRUNAVJHOD-UHFFFAOYSA-N 2-n,2-n,4-n,4-n-tetraethyl-6-(2h-tetrazol-5-yl)-1,3,5-triazine-2,4-diamine Chemical compound CCN(CC)C1=NC(N(CC)CC)=NC(C2=NNN=N2)=N1 CZTUKRUNAVJHOD-UHFFFAOYSA-N 0.000 claims 2
- YJZLSPWOROZXFA-UHFFFAOYSA-N 2-n,4-n-dicyclohexyl-6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound C1CCCCC1NC1=NC(NC2CCCCC2)=NC(C=2C=CC=CC=2)=N1 YJZLSPWOROZXFA-UHFFFAOYSA-N 0.000 claims 2
- XSXCXRISLKQJNC-UHFFFAOYSA-N 4-cyclohexyl-2-cyclohexylimino-6-[3-(3,4-dimethoxyphenyl)-5-methylsulfanylpyrazol-1-yl]-1,3-dihydro-1,3,5-triazin-4-amine Chemical compound C1(CCCCC1)C1(NC(=NC(=N1)NC1CCCCC1)N1N=C(C=C1SC)C1=CC(=C(C=C1)OC)OC)N XSXCXRISLKQJNC-UHFFFAOYSA-N 0.000 claims 2
- YEKATQFXCDVMOM-UHFFFAOYSA-N 4-cyclohexyl-2-cyclohexylimino-6-[5-methylsulfanyl-3-(3,4,5-trimethoxyphenyl)pyrazol-1-yl]-1,3-dihydro-1,3,5-triazin-4-amine Chemical compound C1(CCCCC1)C1(NC(=NC(=N1)NC1CCCCC1)N1N=C(C=C1SC)C1=CC(=C(C(=C1)OC)OC)OC)N YEKATQFXCDVMOM-UHFFFAOYSA-N 0.000 claims 2
- QLORVYPGVIRKJK-UHFFFAOYSA-N CC(C)(C)NC1=NC(N=CN1)(CC2=CC=CC=C2)N Chemical compound CC(C)(C)NC1=NC(N=CN1)(CC2=CC=CC=C2)N QLORVYPGVIRKJK-UHFFFAOYSA-N 0.000 claims 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
- KKXUVEVBRGERMZ-UHFFFAOYSA-N 6-N-benzyl-4-cyclopentyl-2-phenyl-1H-pyrimidine-4,6-diamine Chemical compound C1(CCCC1)C1(NC(=NC(=C1)NCC1=CC=CC=C1)C1=CC=CC=C1)N KKXUVEVBRGERMZ-UHFFFAOYSA-N 0.000 claims 1
- BQDMPXSEKDAUOD-UHFFFAOYSA-N C(C)(CC)NC1=NC(=NC(=N1)NC(C)CC)C1=CC=CC=C1 Chemical compound C(C)(CC)NC1=NC(=NC(=N1)NC(C)CC)C1=CC=CC=C1 BQDMPXSEKDAUOD-UHFFFAOYSA-N 0.000 claims 1
- LAGOKAOEUMWHMF-UHFFFAOYSA-N N1(C=NC=C1)C1=NC(=NC(=N1)NC(C)C)NC(C)C Chemical compound N1(C=NC=C1)C1=NC(=NC(=N1)NC(C)C)NC(C)C LAGOKAOEUMWHMF-UHFFFAOYSA-N 0.000 claims 1
- 108090000854 Oxidoreductases Proteins 0.000 claims 1
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000009826 neoplastic cell growth Effects 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 101000599886 Homo sapiens Isocitrate dehydrogenase [NADP], mitochondrial Proteins 0.000 description 16
- 102100037845 Isocitrate dehydrogenase [NADP], mitochondrial Human genes 0.000 description 16
- 125000001188 haloalkyl group Chemical group 0.000 description 15
- 238000000034 method Methods 0.000 description 12
- HWXBTNAVRSUOJR-UHFFFAOYSA-N 2-hydroxyglutaric acid Chemical compound OC(=O)C(O)CCC(O)=O HWXBTNAVRSUOJR-UHFFFAOYSA-N 0.000 description 11
- 108700028369 Alleles Proteins 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 229940024606 amino acid Drugs 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
- 102200116484 rs121913502 Human genes 0.000 description 4
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 2
- OSYLJQVIKNRXPX-UHFFFAOYSA-N 6-(4-chlorophenyl)-2-N-[4-chloro-3-(trifluoromethyl)phenyl]-4-N-[3-(dimethylamino)propyl]-1,3,5-triazine-2,4-diamine Chemical compound CN(C)CCCNc1nc(Nc2ccc(Cl)c(c2)C(F)(F)F)nc(n1)-c1ccc(Cl)cc1 OSYLJQVIKNRXPX-UHFFFAOYSA-N 0.000 description 2
- CSANMBBDSJFENW-UHFFFAOYSA-N C1(CCCCC1)CNC1=NC(=NC(=N1)N)C1=CC=CC=C1 Chemical compound C1(CCCCC1)CNC1=NC(=NC(=N1)N)C1=CC=CC=C1 CSANMBBDSJFENW-UHFFFAOYSA-N 0.000 description 2
- 0 CC(*=C(C)C(N)=N)=C Chemical compound CC(*=C(C)C(N)=N)=C 0.000 description 2
- ZKLQURKJPPUQQI-UHFFFAOYSA-N CCCNc1nc(Nc2cc(NC(=O)Nc3ccc(Cl)c(c3)C(F)(F)F)ccc2C)nc(n1)-c1ccccc1 Chemical compound CCCNc1nc(Nc2cc(NC(=O)Nc3ccc(Cl)c(c3)C(F)(F)F)ccc2C)nc(n1)-c1ccccc1 ZKLQURKJPPUQQI-UHFFFAOYSA-N 0.000 description 2
- YXDJEDYZJRRTTN-UHFFFAOYSA-N CCN(CC)CCCNc1nc(Nc2cc(cc(c2)C(F)(F)F)C(F)(F)F)nc(n1)-c1ccc(Cl)cc1 Chemical compound CCN(CC)CCCNc1nc(Nc2cc(cc(c2)C(F)(F)F)C(F)(F)F)nc(n1)-c1ccc(Cl)cc1 YXDJEDYZJRRTTN-UHFFFAOYSA-N 0.000 description 2
- KCLBKETVXHZTQK-UHFFFAOYSA-N Cc1ccc(NC(=O)Nc2ccc(Cl)c(c2)C(F)(F)F)cc1Nc1nc(NCC(O)=O)nc(n1)-c1ccncc1 Chemical compound Cc1ccc(NC(=O)Nc2ccc(Cl)c(c2)C(F)(F)F)cc1Nc1nc(NCC(O)=O)nc(n1)-c1ccncc1 KCLBKETVXHZTQK-UHFFFAOYSA-N 0.000 description 2
- ZCUVULNGLKPRBV-UHFFFAOYSA-N Nc1cc(N)nc(n1)-c1ccnc(N)n1 Chemical compound Nc1cc(N)nc(n1)-c1ccnc(N)n1 ZCUVULNGLKPRBV-UHFFFAOYSA-N 0.000 description 2
- JWRUUYZHFGUQRJ-UHFFFAOYSA-N [[4-[[(4-amino-6-pyridin-4-yl-1,3,5-triazin-2-yl)amino]methoxymethylamino]-6-pyridin-4-yl-1,3,5-triazin-2-yl]-(hydroxymethyl)amino]methanol Chemical compound Nc1nc(NCOCNc2nc(nc(n2)-c2ccncc2)N(CO)CO)nc(n1)-c1ccncc1 JWRUUYZHFGUQRJ-UHFFFAOYSA-N 0.000 description 2
- GGYQDUIJPJUTJE-UHFFFAOYSA-N [[4-[[[4-[bis(hydroxymethyl)amino]-6-pyridin-4-yl-1,3,5-triazin-2-yl]amino]methoxymethyl-(hydroxymethyl)amino]-6-pyridin-4-yl-1,3,5-triazin-2-yl]-(hydroxymethyl)amino]methanol Chemical compound OCN(CO)c1nc(NCOCN(CO)c2nc(nc(n2)-c2ccncc2)N(CO)CO)nc(n1)-c1ccncc1 GGYQDUIJPJUTJE-UHFFFAOYSA-N 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- NZGRFUGPKHHITM-UHFFFAOYSA-N n-(2-chloro-6-methylphenyl)-5-[[4-(dimethylamino)-6-pyridin-2-yl-1,3,5-triazin-2-yl]amino]-1,3,4-oxadiazole-2-carboxamide Chemical compound N=1C(C=2N=CC=CC=2)=NC(N(C)C)=NC=1NC(O1)=NN=C1C(=O)NC1=C(C)C=CC=C1Cl NZGRFUGPKHHITM-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000012163 sequencing technique Methods 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 229960004295 valine Drugs 0.000 description 2
- BAUXXSVMIREAEM-UHFFFAOYSA-N 6-n-(5-methyl-1h-pyrazol-3-yl)-4-n-(oxan-4-yl)-2-pyridin-2-ylpyrimidine-4,6-diamine Chemical compound N1C(C)=CC(NC=2N=C(N=C(NC3CCOCC3)C=2)C=2N=CC=CC=2)=N1 BAUXXSVMIREAEM-UHFFFAOYSA-N 0.000 description 1
- RZVUFMDUHKOGEP-UHFFFAOYSA-N C1(=CC=CC=C1)CC1(C=C(N=CN1)N)N Chemical compound C1(=CC=CC=C1)CC1(C=C(N=CN1)N)N RZVUFMDUHKOGEP-UHFFFAOYSA-N 0.000 description 1
- RTBIZGNUMBKVBQ-UHFFFAOYSA-N FCCCC(CCCF)Nc1nc(-c2c(C(F)(F)F)[nH]nc2)nc(NC(CC2)CCC2(F)F)n1 Chemical compound FCCCC(CCCF)Nc1nc(-c2c(C(F)(F)F)[nH]nc2)nc(NC(CC2)CCC2(F)F)n1 RTBIZGNUMBKVBQ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 210000001185 bone marrow Anatomy 0.000 description 1
- 208000035269 cancer or benign tumor Diseases 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNPCT/CN2013/079200 | 2013-07-11 | ||
| PCT/CN2013/079200 WO2015003360A2 (en) | 2013-07-11 | 2013-07-11 | Therapeutically active compounds and their methods of use |
| PCT/CN2014/081957 WO2015003640A1 (en) | 2013-07-11 | 2014-07-10 | Therapeutically active compounds and their methods of use |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019105001A Division JP2019163326A (ja) | 2013-07-11 | 2019-06-05 | 治療活性化合物およびそれらの使用方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016526561A JP2016526561A (ja) | 2016-09-05 |
| JP2016526561A5 true JP2016526561A5 (https=) | 2017-08-17 |
| JP6538037B2 JP6538037B2 (ja) | 2019-07-03 |
Family
ID=52279361
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016524672A Active JP6538037B2 (ja) | 2013-07-11 | 2014-07-10 | 治療活性化合物およびそれらの使用方法 |
| JP2019105001A Pending JP2019163326A (ja) | 2013-07-11 | 2019-06-05 | 治療活性化合物およびそれらの使用方法 |
| JP2021087457A Active JP7450581B2 (ja) | 2013-07-11 | 2021-05-25 | 治療活性化合物およびそれらの使用方法 |
| JP2024032681A Pending JP2024057088A (ja) | 2013-07-11 | 2024-03-05 | 治療活性化合物およびそれらの使用方法 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019105001A Pending JP2019163326A (ja) | 2013-07-11 | 2019-06-05 | 治療活性化合物およびそれらの使用方法 |
| JP2021087457A Active JP7450581B2 (ja) | 2013-07-11 | 2021-05-25 | 治療活性化合物およびそれらの使用方法 |
| JP2024032681A Pending JP2024057088A (ja) | 2013-07-11 | 2024-03-05 | 治療活性化合物およびそれらの使用方法 |
Country Status (39)
Families Citing this family (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120121515A1 (en) | 2009-03-13 | 2012-05-17 | Lenny Dang | Methods and compositions for cell-proliferation-related disorders |
| TWI598337B (zh) | 2009-06-29 | 2017-09-11 | 阿吉歐斯製藥公司 | 治療化合物及組成物 |
| WO2011050210A1 (en) | 2009-10-21 | 2011-04-28 | Agios Pharmaceuticals, Inc. | Methods and compositions for cell-proliferation-related disorders |
| SMT202400081T1 (it) | 2011-05-03 | 2024-03-13 | Agios Pharmaceuticals Inc | Attivatori della piruvato chinasi per uso in terapia |
| CN102827073A (zh) | 2011-06-17 | 2012-12-19 | 安吉奥斯医药品有限公司 | 治疗活性组合物和它们的使用方法 |
| CN102827170A (zh) | 2011-06-17 | 2012-12-19 | 安吉奥斯医药品有限公司 | 治疗活性组合物和它们的使用方法 |
| PE20142098A1 (es) | 2012-01-06 | 2015-01-08 | Agios Pharmaceuticals Inc | Compuestos terapeuticamente activos y sus metodos de uso |
| US9474779B2 (en) | 2012-01-19 | 2016-10-25 | Agios Pharmaceuticals, Inc. | Therapeutically active compositions and their methods of use |
| EP2906212A4 (en) | 2012-10-15 | 2016-06-08 | Agios Pharmaceuticals Inc | THERAPEUTIC COMPOUNDS AND COMPOSITIONS |
| US9447026B2 (en) | 2013-03-14 | 2016-09-20 | Kalyra Pharmaceuticals, Inc. | Bicyclic analgesic compounds |
| WO2015003360A2 (en) * | 2013-07-11 | 2015-01-15 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| CN105593215B (zh) | 2013-07-11 | 2019-01-15 | 安吉奥斯医药品有限公司 | 用于治疗癌症的作为idh2突变体抑制剂的2,4-或4,6-二氨基嘧啶化合物 |
| AU2014287122B9 (en) | 2013-07-11 | 2018-11-01 | Les Laboratoires Servier | N,6-bis(aryl or heteroaryl)-1,3,5-triazine-2,4-diamine compounds as IDH2 mutants inhibitors for the treatment of cancer |
| WO2015003355A2 (en) | 2013-07-11 | 2015-01-15 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| WO2015010297A1 (en) | 2013-07-25 | 2015-01-29 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| AU2014295938B2 (en) | 2013-08-02 | 2018-07-19 | Les Laboratoires Servier | Therapeutically active compounds and their methods of use |
| CA2932039A1 (en) | 2013-12-12 | 2015-06-18 | Kalyra Pharmaceuticals, Inc. | Bicyclic alkyl compounds and synthesis |
| CN113336653A (zh) | 2014-03-07 | 2021-09-03 | 里科瑞尔姆Ip控股有限责任公司 | 螺桨烷衍生物及合成 |
| NZ723859A (en) | 2014-03-14 | 2023-01-27 | Servier Lab | Pharmaceutical compositions of therapeutically active compounds and their uses |
| US10308609B2 (en) | 2014-09-17 | 2019-06-04 | Zeno Royalties & Milestones, LLC | Bicyclic compounds |
| JP2017529382A (ja) | 2014-09-29 | 2017-10-05 | アギオス ファーマシューティカルス，インコーポレーテッド | 治療活性を有する化合物及びその使用方法 |
| CN104672093B (zh) * | 2015-03-22 | 2016-04-13 | 成都塞恩斯医药科技有限公司 | 一种双环丙基甲胺的制备方法 |
| CA2989111C (en) | 2015-06-11 | 2023-10-03 | Agios Pharmaceuticals, Inc. | Methods of using pyruvate kinase activators |
| DK3330258T3 (da) * | 2015-07-30 | 2021-08-16 | Chia Tai Tianqing Pharmaceutical Group Co Ltd | 1, 3, 5-triazinderivat og fremgangsmåde til anvendelse af samme |
| US9751863B2 (en) * | 2015-08-05 | 2017-09-05 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| KR102699521B1 (ko) | 2015-10-15 | 2024-08-26 | 르 라보레또레 쎄르비에르 | 악성 종양의 치료를 위한 조합물 요법 |
| FI3362065T3 (fi) | 2015-10-15 | 2024-06-19 | Servier Lab | Ivosidenibiä, sytarabiinia ja daunorubisiinia tai idarubisiinia käsittävä yhdistelmähoito akuutin myelooisen leukemian hoitamiseksi |
| CA3002531C (en) | 2015-10-21 | 2020-08-18 | NeuForm Pharmaceuticals, Inc. | Deuterated compounds for treating hematologic malignancies, and compositions and methods thereof |
| WO2017140758A1 (en) | 2016-02-19 | 2017-08-24 | Debiopharm International S.A. | Derivatives of 2-amino-4-(2-oxazolidinon-3-yl)-pyrimidine fused with a five-membered heteroaromatic ring in 5,6-position which are useful for the treatment of various cancers |
| US20190060257A1 (en) * | 2016-03-16 | 2019-02-28 | Zeno Royalties & Milestones, LLC | Analgesic compounds |
| CA3026149A1 (en) * | 2016-06-02 | 2017-12-07 | Cadent Therapeutics, Inc. | Potassium channel modulators |
| KR102232614B1 (ko) * | 2016-07-21 | 2021-03-29 | 난징 산홈 팔마세우티칼 컴퍼니 리미티드 | 이소시트레이트 탈수소효소 억제제의 화학적 화합물 및 이의 적용 |
| WO2018019693A1 (de) * | 2016-07-28 | 2018-02-01 | Bayer Cropscience Aktiengesellschaft | Verfahren zur herstellung von fluoralkylnitrilen und den entsprechenden fluoralkyltetrazolen |
| SI3571193T1 (sl) | 2017-01-23 | 2022-04-29 | Cadent Therapeutics, Inc. | Modulatorji kalijevega kanalčka |
| US11242327B2 (en) | 2017-05-15 | 2022-02-08 | Recurium Ip Holdings, Llc | Analgesic compounds |
| CA3067035A1 (en) | 2017-06-12 | 2018-12-20 | Agios Pharmaceuticals, Inc. | Methods of treating brain tumors using combination therapy |
| US12064436B2 (en) | 2017-06-12 | 2024-08-20 | Servier Pharmaceuticals Llc | Methods of treating brain tumors using combination therapy |
| KR20200020899A (ko) | 2017-06-30 | 2020-02-26 | 셀진 코포레이션 | 2-(4-클로로페닐)-n-((2-(2,6-디옥소피페리딘-3-일)-1-옥소이소인돌린-5-일)메틸)-2,2-디플루오로아세트아미드의 조성물 및 사용 방법 |
| CN109265444B (zh) * | 2017-07-17 | 2022-03-11 | 南京圣和药业股份有限公司 | 取代的三嗪类idh抑制剂的光学异构体及其应用 |
| CN109467538A (zh) | 2017-09-07 | 2019-03-15 | 和记黄埔医药（上海）有限公司 | 环烯烃取代的杂芳环类化合物及其用途 |
| CN118359585A (zh) * | 2017-11-02 | 2024-07-19 | 法国施维雅药厂 | 共晶体、其药物组合物以及涉及其的治疗方法 |
| US10980788B2 (en) | 2018-06-08 | 2021-04-20 | Agios Pharmaceuticals, Inc. | Therapy for treating malignancies |
| US11407717B2 (en) | 2018-06-26 | 2022-08-09 | Kpc Pharmaceuticals, Inc. | Benzimidazole derivatives and use thereof as IDH1 inhibitors |
| CA3116339A1 (en) | 2018-10-22 | 2020-04-30 | Cadent Therapeutics, Inc. | Crystalline forms of potassium channel modulators |
| JP7736678B2 (ja) | 2019-10-16 | 2025-09-09 | ケモセントリックス，インコーポレイティド | Ｐｄ－ｌ１疾患の処置のためのヘテロアリール－ビフェニルアミド |
| US20200085832A1 (en) | 2019-11-22 | 2020-03-19 | Agios Pharmaceuticals, Inc. | Deuterated analogs of an organic compound |
| EP4186525A4 (en) | 2020-07-21 | 2024-04-03 | Daiichi Sankyo Company, Limited | COMBINATION OF TEMOZOLOMIDE AND INHIBITOR OF THE MUTANT IDH1 ENZYME |
| CN112321571B (zh) * | 2020-10-27 | 2022-06-03 | 浙江工业大学 | 2-呋喃-喹啉-4-甲酰胺类化合物及其应用 |
| KR20230145402A (ko) * | 2021-02-12 | 2023-10-17 | 르 라보레또레 쎄르비에르 | 치료적 활성 화합물 및 이의 사용 방법 |
| US11865079B2 (en) * | 2021-02-12 | 2024-01-09 | Servier Pharmaceuticals Llc | Therapeutically active compounds and their methods of use |
| CN113461660B (zh) * | 2021-06-11 | 2022-08-02 | 浙江大学 | 2,4,6-三取代-1,3,5-均三嗪类化合物及制备和应用 |
| CN118355008A (zh) * | 2022-01-11 | 2024-07-16 | 正大天晴药业集团股份有限公司 | 一种1,3,5-三嗪衍生物的制备方法 |
| CN118786119A (zh) * | 2022-03-15 | 2024-10-15 | 贝达药业股份有限公司 | 突变型idh1和idh2抑制剂及其应用 |
| WO2023192565A1 (en) | 2022-03-31 | 2023-10-05 | Servier Pharmaceuticals Llc | Methods of treating enhancing brain tumors using combination therapy |
| CN114773320A (zh) * | 2022-05-29 | 2022-07-22 | 重庆医科大学 | 1,3,5-三嗪化合物及其制备方法和用途 |
| CN116102509A (zh) * | 2022-12-16 | 2023-05-12 | 浙江工业大学 | 一种二氟甲基硫醚类化合物及其制备方法和应用 |
| WO2024137979A2 (en) * | 2022-12-23 | 2024-06-27 | University Of Pittsburgh - Of The Commonwealth System Of Higher Education | Foxm1 inhibitors and their use in treating cancers |
| AR133332A1 (es) | 2023-07-25 | 2025-09-17 | Servier Lab | Sales, cocristales, composiciones farmacéuticas de los mismos, y métodos de tratamiento que implican los mismos |
| EP4538262A1 (en) | 2023-10-12 | 2025-04-16 | Sandoz Ag | Cocrystals of vorasidenib |
| CN117586228A (zh) * | 2023-12-01 | 2024-02-23 | 上海彩迩文生化科技有限公司 | 一种三嗪类药物的制备方法 |
| US20250257050A1 (en) | 2024-02-09 | 2025-08-14 | Les Laboratoires Servier | Process for the preparation of vorasidenib |
Family Cites Families (186)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2390529A (en) | 1942-02-03 | 1945-12-11 | Ernst A H Friedheim | Hydrazino-1,3,5-triazino derivatives of substituted phenylarsenic compounds |
| NL125847C (https=) * | 1963-02-15 | |||
| BE754242A (fr) * | 1970-07-15 | 1971-02-01 | Geigy Ag J R | Diamino-s-triazines et dinitro-s-triazines |
| US3867383A (en) * | 1971-03-29 | 1975-02-18 | Ciba Geigy Corp | Monoanthranilatoanilino-s-triazines |
| US3681332A (en) * | 1971-04-13 | 1972-08-01 | Lilly Industries Ltd | Dihalo-s-triazine compounds |
| BE793501A (fr) * | 1971-12-31 | 1973-06-29 | Ciba Geigy | Composes heterocycliques et produits phytopharmaceutiques qui en contiennent |
| CH606334A5 (https=) * | 1974-06-21 | 1978-10-31 | Ciba Geigy Ag | |
| JPS5170779A (ja) * | 1974-12-17 | 1976-06-18 | Nippon Shinyaku Co Ltd | Shinkinaguanamidoruino seiho |
| DE2715984A1 (de) | 1977-04-09 | 1978-10-26 | Basf Ag | Farbstoffzubereitungen fuer cellulose und cellulosehaltiges textilmaterial |
| DE2737984A1 (de) | 1977-08-23 | 1979-03-08 | Lentia Gmbh | Verfahren zur herstellung von lagerstabilen und vergilbungsfrei einbrennbaren lackharzen |
| DE2928485A1 (de) | 1979-07-14 | 1981-01-29 | Bayer Ag | Verwendung von harnstoffderivaten als arzneimittel bei der behandlung von fettstoffwechselstoerungen |
| JPS5655302A (en) * | 1979-10-15 | 1981-05-15 | Hokko Chem Ind Co Ltd | Fungicide for agriculture and horticulture |
| DE3103110A1 (de) * | 1981-01-30 | 1982-08-26 | Basf Ag, 6700 Ludwigshafen | Triazingruppenhaltige verbindungen |
| JPS58186682A (ja) | 1982-04-27 | 1983-10-31 | 日本化薬株式会社 | セルロ−ス又はセルロ−ス含有繊維材料の染色法 |
| DE3512630A1 (de) | 1985-04-06 | 1986-10-23 | Hoechst Ag, 6230 Frankfurt | Verfahren zum faerben oder bedrucken von cellulosefasern oder cellulosemischfasern |
| US5041443A (en) | 1989-02-21 | 1991-08-20 | Dainippon Pharmaceutical Co., Ltd. | Medicament for treating cerebral insufficiency diseases, novel 2-(1-piperazinyl)-4-phenylcycloalkanopyrimidine derivatives, and process for the production thereof |
| DK0385237T3 (da) | 1989-03-03 | 1994-07-25 | Dainippon Pharmaceutical Co | 2-(1-Piperazinyl)-4-phenylcycloalkanopyridinderivater, fremgangsmåde til fremstilling deraf og farmaceutisk præparat indeholdende dem |
| DE3922735A1 (de) * | 1989-07-11 | 1991-01-24 | Hoechst Ag | Aminopyrimidin-derivate, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung als fungizide |
| JPH0491034A (ja) | 1990-08-02 | 1992-03-24 | Fujimoto Daiagunosuteitsukusu:Kk | 中枢神経保護剤 |
| JPH0499768A (ja) | 1990-08-17 | 1992-03-31 | Dainippon Pharmaceut Co Ltd | ４―（４―フェニルピリジン―２―イル）ピペラジン―１―オキシド誘導体 |
| JPH05140126A (ja) * | 1991-11-26 | 1993-06-08 | Hokko Chem Ind Co Ltd | トリアゾール誘導体および除草剤 |
| CA2131004A1 (en) * | 1992-02-28 | 1993-09-02 | Hideshi Kobayashi | S-triazine derivative and remedy for estrogen-dependent disease containing said derivative as effective component |
| US5441563A (en) | 1993-07-06 | 1995-08-15 | Armstrong World Industries, Inc. | Highly insoluble azole embossing inhibitor and the use thereof |
| IL115420A0 (en) | 1994-09-26 | 1995-12-31 | Zeneca Ltd | Aminoheterocyclic derivatives |
| IL117580A0 (en) | 1995-03-29 | 1996-07-23 | Merck & Co Inc | Inhibitors of farnesyl-protein transferase and pharmaceutical compositions containing them |
| JPH08311047A (ja) * | 1995-05-16 | 1996-11-26 | Nissan Chem Ind Ltd | シアノエチルメラミン誘導体およびその製造方法 |
| FR2735127B1 (fr) | 1995-06-09 | 1997-08-22 | Pf Medicament | Nouvelles piperazines heteroaromatiques utiles comme medicaments. |
| AU6015896A (en) | 1995-06-15 | 1997-01-15 | Nissan Chemical Industries Ltd. | Epoxy/acid anhydride composition |
| ES2100129B1 (es) | 1995-10-11 | 1998-02-16 | Medichem Sa | Nuevos compuestos aminopiridinicos policiclicos inhibidores de acetilcolinesterasa, procedimiento para su preparacion y su utilizacion. |
| US6313127B1 (en) | 1996-02-02 | 2001-11-06 | Zeneca Limited | Heterocyclic compounds useful as pharmaceutical agents |
| GB9602166D0 (en) | 1996-02-02 | 1996-04-03 | Zeneca Ltd | Aminoheterocyclic derivatives |
| US5807876A (en) | 1996-04-23 | 1998-09-15 | Vertex Pharmaceuticals Incorporated | Inhibitors of IMPDH enzyme |
| JPH09291034A (ja) | 1996-02-27 | 1997-11-11 | Yoshitomi Pharmaceut Ind Ltd | 縮合ピリジン化合物およびその医薬としての用途 |
| US6262113B1 (en) | 1996-03-20 | 2001-07-17 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| AU722662B2 (en) | 1996-05-20 | 2000-08-10 | Darwin Discovery Limited | Quinoline sulfonamides as TNF inhibitors and as PDE-IV inhibitors |
| US5984882A (en) | 1996-08-19 | 1999-11-16 | Angiosonics Inc. | Methods for prevention and treatment of cancer and other proliferative diseases with ultrasonic energy |
| CA2271744A1 (en) | 1996-11-14 | 1998-05-22 | Isao Hashiba | Cyanoethylmelamine derivatives and process for producing the same |
| US6399358B1 (en) | 1997-03-31 | 2002-06-04 | Thomas Jefferson University | Human gene encoding human chondroitin 6-sulfotransferase |
| JPH11158073A (ja) * | 1997-09-26 | 1999-06-15 | Takeda Chem Ind Ltd | アデノシンａ３拮抗剤 |
| DE69814151T2 (de) * | 1997-12-12 | 2004-03-25 | Abbott Laboratories, Abbott Park | Triazin angiogenese-inhibitoren |
| WO1999032463A1 (en) | 1997-12-22 | 1999-07-01 | Bayer Corporation | INHIBITION OF p38 KINASE USING SYMMETRICAL AND UNSYMMETRICAL DIPHENYL UREAS |
| US7517880B2 (en) | 1997-12-22 | 2009-04-14 | Bayer Pharmaceuticals Corporation | Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas |
| WO2000002864A1 (en) | 1998-07-10 | 2000-01-20 | Martens Juergen | Precusors for pna-monomers |
| US6783965B1 (en) | 2000-02-10 | 2004-08-31 | Mountain View Pharmaceuticals, Inc. | Aggregate-free urate oxidase for preparation of non-immunogenic polymer conjugates |
| ATE498409T1 (de) | 1998-08-06 | 2011-03-15 | Mountain View Pharmaceuticals | Peg-uricase konjugate und verwendung davon |
| WO2000025780A1 (en) | 1998-10-29 | 2000-05-11 | Bristol-Myers Squibb Company | Compounds derived from an amine nucleus that are inhibitors of impdh enzyme |
| UY25842A1 (es) | 1998-12-16 | 2001-04-30 | Smithkline Beecham Corp | Antagonistas de receptores de il-8 |
| AU5379900A (en) | 1999-06-07 | 2000-12-28 | Shire Biochem Inc. | Thiophene integrin inhibitors |
| WO2001016097A1 (en) | 1999-08-27 | 2001-03-08 | Sugen, Inc. | Phosphate mimics and methods of treatment using phosphatase inhibitors |
| CZ2002959A3 (cs) | 1999-09-17 | 2002-07-17 | Millennium Pharmaceuticals, Inc. | Inhibitory faktoru Xa |
| ES2316383T3 (es) | 1999-09-17 | 2009-04-16 | Millennium Pharmaceuticals, Inc. | Benzamidas e inhibidores relacionados del factor xa. |
| EP1246823A1 (en) | 1999-12-28 | 2002-10-09 | Pharmacopeia, Inc. | Pyrimidine and triazine kinase inhibitors |
| WO2001064642A2 (en) | 2000-02-29 | 2001-09-07 | Cor Therapeutics, Inc. | Benzamides and related inhibitors of factor xa |
| EP1301484A2 (en) | 2000-07-20 | 2003-04-16 | Neurogen Corporation | Capsaicin receptor ligands |
| JP4113323B2 (ja) * | 2000-08-07 | 2008-07-09 | 富士フイルム株式会社 | アゾ色素及びそれを含むインクジェット記録用インク、並びにインクジェット記録方法 |
| US6525091B2 (en) | 2001-03-07 | 2003-02-25 | Telik, Inc. | Substituted diarylureas as stimulators for Fas-mediated apoptosis |
| EP1389194A2 (en) | 2001-04-27 | 2004-02-18 | Vertex Pharmaceuticals Incorporated | Inhibitors of bace |
| CN1800185A (zh) | 2001-06-11 | 2006-07-12 | 比奥维特罗姆股份公司 | 取代的磺酰胺化合物、其制备方法及其作为治疗cns疾病、肥胖和ii型糖尿病的药物的应用 |
| CA2450934A1 (en) | 2001-06-19 | 2002-12-27 | Marco Dodier | Pyrimidine inhibitors of phosphodiesterase (pde) 7 |
| DE60238066D1 (de) * | 2001-08-17 | 2010-12-02 | Basf Se | Triazinderivate und deren verwendung als sonnenschutzmittel |
| JP4753336B2 (ja) * | 2001-09-04 | 2011-08-24 | 日本化薬株式会社 | 新規アリル化合物及びその製法 |
| US20060217516A1 (en) | 2001-12-21 | 2006-09-28 | Casati Francois M | Tertiary amine modified polyurethane products made therefrom |
| US6878196B2 (en) | 2002-01-15 | 2005-04-12 | Fuji Photo Film Co., Ltd. | Ink, ink jet recording method and azo compound |
| EP1485381B8 (en) | 2002-03-15 | 2010-05-12 | Vertex Pharmaceuticals Incorporated | Azolylaminoazine as inhibitors of protein kinases |
| TWI319387B (en) * | 2002-04-05 | 2010-01-11 | Astrazeneca Ab | Benzamide derivatives |
| US20040067234A1 (en) | 2002-07-11 | 2004-04-08 | Paz Einat | Isocitrate dehydrogenase and uses thereof |
| EP2256108B1 (en) | 2002-07-18 | 2016-03-23 | Janssen Pharmaceutica NV | Substituted triazine kinase inhibitors |
| JP2004083610A (ja) * | 2002-08-22 | 2004-03-18 | Fuji Photo Film Co Ltd | インクセット、インクカートリッジ、記録方法、プリンター及び記録物 |
| JP2004107220A (ja) * | 2002-09-13 | 2004-04-08 | Mitsubishi Pharma Corp | ＴＮＦ−α産生抑制剤 |
| TWI335913B (en) | 2002-11-15 | 2011-01-11 | Vertex Pharma | Diaminotriazoles useful as inhibitors of protein kinases |
| WO2004050033A2 (en) | 2002-12-02 | 2004-06-17 | Arqule, Inc. | Method of treating cancers |
| NZ541050A (en) | 2002-12-16 | 2010-06-25 | Genmab As | Human monoclonal antibodies against interleukin 8 (IL-8) |
| WO2004062604A2 (en) | 2003-01-10 | 2004-07-29 | Threshold Pharmaceuticals, Inc. | Treatment of cancer with 2-deoxyglucose |
| US7358262B2 (en) | 2003-01-29 | 2008-04-15 | Whitehead Institute For Biomedical Research | Identification of genotype-selective anti-tumor agents |
| WO2004073619A2 (en) | 2003-02-14 | 2004-09-02 | Smithkline Beecham Corporation | Ccr8 antagonists |
| WO2004074438A2 (en) | 2003-02-14 | 2004-09-02 | Smithkline Beecham Corporation | Ccr8 antagonists |
| ATE482747T1 (de) | 2003-04-11 | 2010-10-15 | High Point Pharmaceuticals Llc | Neue amide derivate und deren pharmazeutische verwendungen |
| WO2004099163A1 (en) | 2003-05-05 | 2004-11-18 | New York University | Solid phase synthesis of biaryl triazine library by suzuki cross-coupling reaction |
| WO2005003103A2 (en) | 2003-06-30 | 2005-01-13 | Astrazeneca Ab | 2, 4, 6-tri-substituted 6-membered heterocycles and their use in the treatment of neurodegenerative diseases |
| WO2005013982A1 (en) | 2003-08-06 | 2005-02-17 | Vertex Pharmaceuticals Incorporated | Aminotriazole compounds useful as inhibitors of protein kinases |
| WO2005035507A2 (en) | 2003-10-10 | 2005-04-21 | Bayer Pharmaceuticals Corporation | 4-aminopyrimidine derivatives for treatment of hyperproliferative disorders |
| JP4099768B2 (ja) | 2003-11-10 | 2008-06-11 | 富士電機デバイステクノロジー株式会社 | 電子写真感光体および該電子写真感光体に起因する干渉縞有無の判定方法 |
| US20070196395A1 (en) | 2003-12-12 | 2007-08-23 | Mackerell Alexander | Immunomodulatory compounds that target and inhibit the py'binding site of tyrosene kinase p56 lck sh2 domain |
| MXPA06008157A (es) | 2003-12-24 | 2007-09-07 | Johnson & Johnson | Tratamiento de gliomas malignos con inhibidores de factor de crecimiento transformante-beta. |
| JP2005264016A (ja) * | 2004-03-19 | 2005-09-29 | Fuji Photo Film Co Ltd | インクジェット記録用インク、インクセット及びインクジェット記録方法 |
| US7335770B2 (en) | 2004-03-24 | 2008-02-26 | Reddy U5 Therapeutics, Inc. | Triazine compounds and their analogs, compositions, and methods |
| GB0412526D0 (en) | 2004-06-05 | 2004-07-14 | Leuven K U Res & Dev | Type 2 diabetes |
| BRPI0515500A (pt) | 2004-09-20 | 2008-07-29 | Xenon Pharmaceuticals Inc | derivados piridazina para inibição de estearoil-coa-desaturase |
| CA2581454A1 (en) | 2004-09-23 | 2006-03-30 | Reddy Us Therapeutics, Inc. | Novel pyrimidine compounds, process for their preparation and compositions containing them |
| WO2006038594A1 (ja) | 2004-10-04 | 2006-04-13 | Ono Pharmaceutical Co., Ltd. | Ｎ型カルシウムチャネル阻害薬 |
| WO2006070198A1 (en) | 2004-12-30 | 2006-07-06 | Astex Therapeutics Limited | Pyrazole derivatives as that modulate the activity of cdk, gsk and aurora kinases |
| CN101146789A (zh) | 2005-01-25 | 2008-03-19 | 阿斯利康(瑞典)有限公司 | 化合物 |
| MX2007012548A (es) | 2005-04-11 | 2008-03-11 | Savient Pharmaceuticals Inc | Formas variantes de urato oxidasa y uso de las mismas. |
| ES2624863T3 (es) | 2005-06-08 | 2017-07-17 | Millennium Pharmaceuticals, Inc. | Métodos para identificación, evaluación, y tratamiento de pacientes con terapia de cáncer |
| GB0513702D0 (en) | 2005-07-04 | 2005-08-10 | Sterix Ltd | Compound |
| US8071597B2 (en) | 2005-08-26 | 2011-12-06 | Merck Serono Sa | Pyrazine compounds and uses as PI3K inhibitors |
| US8133900B2 (en) | 2005-11-01 | 2012-03-13 | Targegen, Inc. | Use of bi-aryl meta-pyrimidine inhibitors of kinases |
| JP4753363B2 (ja) | 2005-12-28 | 2011-08-24 | 株式会社ジョイコシステムズ | 遊技媒体貸出装置用設定アダプタ、遊技媒体貸出装置用設定アダプタ付き接続ケーブルおよび遊技媒体貸出システム |
| WO2007095812A1 (en) | 2006-02-27 | 2007-08-30 | Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences | Substituted [1,3,5] triazine compounds, their processes for preparation and uses thereof |
| TW200815426A (en) | 2006-06-28 | 2008-04-01 | Astrazeneca Ab | New pyridine analogues II 333 |
| US20100297673A1 (en) | 2006-09-20 | 2010-11-25 | Reddy Us Therapeutics | Methods and compositions for upregulation of peroxiredoxin activity |
| US7906555B2 (en) | 2006-10-26 | 2011-03-15 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Aquaporin modulators and methods of using them for the treatment of edema and fluid imbalance |
| HUP0600810A3 (en) | 2006-10-27 | 2008-09-29 | Richter Gedeon Nyrt | New sulfonamide derivatives as bradykinin antagonists, process and intermediates for their preparation and pharmaceutical compositions containing them |
| PE20081229A1 (es) | 2006-12-01 | 2008-08-28 | Merck & Co Inc | Antagonistas de receptor de orexina de diazepam sustituido |
| JP2010511727A (ja) | 2006-12-04 | 2010-04-15 | ニューロクライン バイオサイエンシーズ，インコーポレイテッド | アデノシン受容体アンタゴニストとしての置換ピリミジン |
| KR101472765B1 (ko) | 2006-12-08 | 2014-12-15 | 밀레니엄 파머슈티컬스 인코퍼레이티드 | 경구용 Ｘａ 인자 억제제를 포함하는 단위 용량 제형 및 경구용 Ｘａ 인자 억제제를 사용하는 혈전증의 치료 방법 |
| WO2008076883A2 (en) * | 2006-12-15 | 2008-06-26 | Abraxis Bioscience, Inc. | Triazine derivatives and their therapeutical applications |
| JP5450381B2 (ja) | 2007-04-30 | 2014-03-26 | プロメティック・バイオサイエンスィズ・インコーポレーテッド | 化合物、そのような化合物を含有する組成物、及びそのような化合物を用いるがん及び自己免疫疾患の治療法 |
| EP2166849A4 (en) | 2007-06-11 | 2010-09-15 | Miikana Therapeutics Inc | SUBSTITUTED PYRAZOL COMPOUNDS |
| PT2176231T (pt) | 2007-07-20 | 2016-12-09 | Nerviano Medical Sciences Srl | Derivados de indazol substituídos activos como inibidores de quinases |
| US8415340B2 (en) | 2007-07-25 | 2013-04-09 | Bristol-Myers Squibb Company | Triazine kinase inhibitors |
| TW200906818A (en) | 2007-07-31 | 2009-02-16 | Astrazeneca Ab | Chemical compounds |
| WO2009048101A1 (ja) | 2007-10-10 | 2009-04-16 | Takeda Pharmaceutical Company Limited | アミド化合物 |
| WO2009049157A1 (en) | 2007-10-11 | 2009-04-16 | Smithkline Beecham Corporation | Novel seh inhibitors and their use |
| WO2009091388A2 (en) | 2007-12-21 | 2009-07-23 | Progenics Pharmaceuticals, Inc. | Triazines and related compounds having antiviral activity, compositions and methods thereof |
| WO2009086303A2 (en) | 2007-12-21 | 2009-07-09 | University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
| GB0805477D0 (en) | 2008-03-26 | 2008-04-30 | Univ Nottingham | Pyrimidines triazines and their use as pharmaceutical agents |
| JP5277685B2 (ja) * | 2008-03-26 | 2013-08-28 | 富士ゼロックス株式会社 | 電子写真感光体、画像形成装置、プロセスカートリッジ及び画像形成方法 |
| US20090281089A1 (en) | 2008-04-11 | 2009-11-12 | Genentech, Inc. | Pyridyl inhibitors of hedgehog signalling |
| CN101575408B (zh) | 2008-05-09 | 2013-10-30 | Mca技术有限公司 | 用作阻燃剂和光稳定剂的聚三嗪基化合物 |
| KR20110017445A (ko) | 2008-06-11 | 2011-02-21 | 아스트라제네카 아베 | 암 및 골수증식성 장애의 치료에 유용한 트리시클릭 2,4-디아미노-ｌ,3,5-트리아진 유도체 |
| FR2932483A1 (fr) | 2008-06-13 | 2009-12-18 | Cytomics Systems | Composes utiles pour le traitement des cancers. |
| CN101307029B (zh) | 2008-07-08 | 2011-04-13 | 浙江大学 | 2,4,6-三取代-1,3,5-三嗪类衍生物库及制备方法 |
| WO2010007756A1 (ja) | 2008-07-14 | 2010-01-21 | 塩野義製薬株式会社 | Ｔｔｋ阻害作用を有するピリジン誘導体 |
| US20100144722A1 (en) | 2008-09-03 | 2010-06-10 | Dr. Reddy's Laboratories Ltd. | Novel heterocyclic compounds as gata modulators |
| US8685660B2 (en) | 2008-09-03 | 2014-04-01 | The Johns Hopkins University | Genetic alterations in isocitrate dehydrogenase and other genes in malignant glioma |
| JP2010079130A (ja) * | 2008-09-29 | 2010-04-08 | Fuji Xerox Co Ltd | 電子写真感光体、プロセスカートリッジ、及び画像形成装置 |
| JP2012509321A (ja) | 2008-11-21 | 2012-04-19 | ミレニアム ファーマシューティカルズ， インコーポレイテッド | 癌および他の疾患または障害の処置のための、４−［６−メトキシ−７−（３−ピペリジン−１−イル−プロポキシ）キナゾリン−４−イル］ピペラジン−１−カルボン酸（４−イソプロポキシフェニル）−アミドの乳酸塩およびその薬学的組成物 |
| JP2010181540A (ja) * | 2009-02-04 | 2010-08-19 | Fuji Xerox Co Ltd | 電子写真感光体、プロセスカートリッジ、及び画像形成装置 |
| US8673891B2 (en) | 2009-02-06 | 2014-03-18 | Nippon Shinyaku Co., Ltd. | Aminopyrazine derivative and medicine |
| US20120121515A1 (en) | 2009-03-13 | 2012-05-17 | Lenny Dang | Methods and compositions for cell-proliferation-related disorders |
| CA2760363C (en) | 2009-05-04 | 2015-10-20 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Selective access to cryopreserved samples |
| DK2427441T3 (en) | 2009-05-04 | 2017-03-20 | Agios Pharmaceuticals Inc | PKM2 Activators for use in the treatment of cancer |
| WO2010130638A1 (en) | 2009-05-14 | 2010-11-18 | Evotec Ag | Sulfonamide compounds, pharmaceutical compositions and uses thereof |
| BRPI1010887A2 (pt) | 2009-06-08 | 2016-12-27 | California Capital Equity Llc | derivados de triazina e suas aplicações terapêuticas. |
| WO2010144338A1 (en) * | 2009-06-08 | 2010-12-16 | Abraxis Bioscience, Llc | Triazine derivatives and their therapeutical applications |
| WO2010144522A1 (en) | 2009-06-09 | 2010-12-16 | Abraxis Bioscience, Llc | Ureidophenyl substituted triazine derivatives and their therapeutical applications |
| EP2440053A4 (en) | 2009-06-09 | 2012-10-31 | California Capital Equity Llc | BENZYL SUBSTITUTED TRIAZINE DERIVATIVES AND THERAPEUTIC APPLICATIONS THEREOF |
| JP2012529518A (ja) | 2009-06-09 | 2012-11-22 | アブラクシス バイオサイエンス リミテッド ライアビリティー カンパニー | ヘッジホッグシグナル伝達のピリジル−トリアジン阻害剤 |
| TWI598337B (zh) | 2009-06-29 | 2017-09-11 | 阿吉歐斯製藥公司 | 治療化合物及組成物 |
| ES2582535T3 (es) | 2009-07-10 | 2016-09-13 | Kirk Promotion Ltd. | Dispositivo de articulación de la rodilla |
| EP3103452A1 (en) * | 2009-08-25 | 2016-12-14 | Abraxis BioScience, LLC | Combination therapy with nanoparticle compositions of taxane and hedgehog inhibitors |
| JP2013503846A (ja) | 2009-09-01 | 2013-02-04 | ファイザー・インク | ベンズイミダゾール誘導体 |
| WO2011032169A2 (en) | 2009-09-14 | 2011-03-17 | Phusis Therapeutics Inc. | Pharmaceutical compositions and formulations including inhibitors of the pleckstrin homology domain and methods for using same |
| JP5473851B2 (ja) * | 2009-09-30 | 2014-04-16 | 富士フイルム株式会社 | 高分子フィルム、位相差フィルム、偏光板及び液晶表示装置 |
| US8652534B2 (en) | 2009-10-14 | 2014-02-18 | Berry Pharmaceuticals, LLC | Compositions and methods for treatment of mammalian skin |
| EP2525790B1 (en) | 2009-10-21 | 2020-05-27 | Agios Pharmaceuticals, Inc. | Methods and compositions for cell-proliferation-related disorders |
| WO2011050210A1 (en) | 2009-10-21 | 2011-04-28 | Agios Pharmaceuticals, Inc. | Methods and compositions for cell-proliferation-related disorders |
| CN102574843B (zh) | 2009-10-22 | 2015-06-17 | 法博太科制药有限公司 | 抗纤维化剂的稠环类似物 |
| ES2642109T3 (es) * | 2009-12-09 | 2017-11-15 | Agios Pharmaceuticals, Inc. | Compuestos terapéuticamente activos para su uso en el tratamiento de cáncer caracterizados por tener una mutación de IDH |
| NZ578968A (en) | 2010-02-10 | 2011-03-31 | Allans Sheetmetal And Engineering Services | Fuel feed system for a pellet fire |
| US20130197106A1 (en) | 2010-04-01 | 2013-08-01 | Agios Pharmaceuticals, Inc | Methods of identifying a candidate compound |
| WO2011143160A2 (en) | 2010-05-10 | 2011-11-17 | The Johns Hopkins University | Metabolic inhibitor against tumors having an idh mutation |
| US10064885B2 (en) | 2010-07-09 | 2018-09-04 | Massachusetts Institute Of Technology | Metabolic gene, enzyme, and flux targets for cancer therapy |
| CN103097340B (zh) | 2010-07-16 | 2018-03-16 | 安吉奥斯医药品有限公司 | 治疗活性组合物及其使用方法 |
| KR20190120458A (ko) | 2010-10-21 | 2019-10-23 | 메디베이션 테크놀로지즈 엘엘씨 | 결정질의 (8s,9r)-5-플루오로-8-(4-플루오로페닐)-9-(1-메틸-1h-1,2,4-트리아졸-5-일)-8,9-디하이드로-2h-피리도[4,3,2-de]프탈라진-3(7h)-온 토실레이트 염 |
| AU2011336764B2 (en) * | 2010-11-29 | 2017-02-23 | Galleon Pharmaceuticals, Inc. | Novel compounds as respiratory stimulants for treatment of breathing control disorders or diseases |
| TWI549947B (zh) | 2010-12-29 | 2016-09-21 | 阿吉歐斯製藥公司 | 治療化合物及組成物 |
| WO2012173682A2 (en) | 2011-03-29 | 2012-12-20 | The Broad Institute, Inc. | Compounds and methods for the treatment of isocitrate dehydrognase related diseases |
| CN103608016A (zh) | 2011-05-03 | 2014-02-26 | 安吉奥斯医药品有限公司 | 丙酮酸激酶激活剂在治疗中的用途 |
| TWI555737B (zh) | 2011-05-24 | 2016-11-01 | 拜耳知識產權公司 | 含有硫醯亞胺基團之４－芳基－ｎ－苯基－１，３，５－三氮雜苯－２－胺 |
| CN102827170A (zh) | 2011-06-17 | 2012-12-19 | 安吉奥斯医药品有限公司 | 治疗活性组合物和它们的使用方法 |
| CN102827073A (zh) * | 2011-06-17 | 2012-12-19 | 安吉奥斯医药品有限公司 | 治疗活性组合物和它们的使用方法 |
| CA2840883C (en) * | 2011-07-07 | 2019-07-16 | Merck Patent Gmbh | Substituted azaheterocycles |
| EP3111937B1 (en) | 2011-07-08 | 2020-06-17 | Helmholtz-Zentrum für Infektionsforschung GmbH | Medicament for treatment of liver cancer |
| AU2012287103B2 (en) * | 2011-07-22 | 2017-03-30 | University Of Louisville Research Foundation, Inc. | Anti-biofilm compounds |
| BR112014007310A2 (pt) * | 2011-09-27 | 2017-04-04 | Novartis Ag | 3-pirimidin-4-il-oxazolidin-2-onas como inibidores de idh mutante |
| CN102659765B (zh) * | 2011-12-31 | 2014-09-10 | 沈阳药科大学 | 嘧啶及三嗪类化合物的制备方法和应用 |
| PE20142098A1 (es) * | 2012-01-06 | 2015-01-08 | Agios Pharmaceuticals Inc | Compuestos terapeuticamente activos y sus metodos de uso |
| US9474779B2 (en) | 2012-01-19 | 2016-10-25 | Agios Pharmaceuticals, Inc. | Therapeutically active compositions and their methods of use |
| US20150087600A1 (en) | 2012-01-19 | 2015-03-26 | Agios Pharmaceuticals, Inc | Therapeutically active compounds and their methods of use |
| EP2634259A1 (en) | 2012-03-01 | 2013-09-04 | Deutsches Krebsforschungszentrum | Means and methods for the determination of (D)-2-hydroxyglutarate (D2HG) |
| KR20140131955A (ko) | 2012-03-09 | 2014-11-14 | 카나 바이오사이언스 인코포레이션 | 신규 트리아진 유도체 |
| WO2014015422A1 (en) | 2012-07-27 | 2014-01-30 | Ontario Institute For Cancer Research | Cellulose-based nanoparticles for drug delivery |
| EP2906212A4 (en) | 2012-10-15 | 2016-06-08 | Agios Pharmaceuticals Inc | THERAPEUTIC COMPOUNDS AND COMPOSITIONS |
| NZ746607A (en) | 2012-11-21 | 2019-11-29 | Ptc Therapeutics Inc | Substituted reverse pyrimidine bmi-1 inhibitors |
| WO2015003355A2 (en) | 2013-07-11 | 2015-01-15 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| AU2014287122B9 (en) | 2013-07-11 | 2018-11-01 | Les Laboratoires Servier | N,6-bis(aryl or heteroaryl)-1,3,5-triazine-2,4-diamine compounds as IDH2 mutants inhibitors for the treatment of cancer |
| CN105593215B (zh) | 2013-07-11 | 2019-01-15 | 安吉奥斯医药品有限公司 | 用于治疗癌症的作为idh2突变体抑制剂的2,4-或4,6-二氨基嘧啶化合物 |
| WO2015003360A2 (en) * | 2013-07-11 | 2015-01-15 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| WO2015010297A1 (en) | 2013-07-25 | 2015-01-29 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| AU2014295938B2 (en) | 2013-08-02 | 2018-07-19 | Les Laboratoires Servier | Therapeutically active compounds and their methods of use |
| WO2015018060A1 (en) | 2013-08-09 | 2015-02-12 | Agios Pharmaceuticals, Inc. | Crystalline forms of therapeutically active compounds and use thereof |
| KR102699521B1 (ko) | 2015-10-15 | 2024-08-26 | 르 라보레또레 쎄르비에르 | 악성 종양의 치료를 위한 조합물 요법 |
| KR102232614B1 (ko) | 2016-07-21 | 2021-03-29 | 난징 산홈 팔마세우티칼 컴퍼니 리미티드 | 이소시트레이트 탈수소효소 억제제의 화학적 화합물 및 이의 적용 |
| MX392941B (es) | 2016-09-07 | 2025-03-24 | Celgene Corp | Composiciones para comprimidos. |
-
2013
- 2013-07-11 WO PCT/CN2013/079200 patent/WO2015003360A2/en not_active Ceased
-
2014
- 2014-07-09 SM SM20200102T patent/SMT202000102T1/it unknown
- 2014-07-10 CR CR20200479A patent/CR20200479A/es unknown
- 2014-07-10 BR BR112016000561A patent/BR112016000561B8/pt not_active IP Right Cessation
- 2014-07-10 EA EA201890411A patent/EA201890411A1/ru unknown
- 2014-07-10 EA EA201690206A patent/EA030199B9/ru unknown
- 2014-07-10 BR BR122017014843-5A patent/BR122017014843B1/pt active IP Right Grant
- 2014-07-10 NZ NZ754946A patent/NZ754946A/en unknown
- 2014-07-10 EP EP14822106.2A patent/EP3019483B1/en active Active
- 2014-07-10 EP EP19209249.2A patent/EP3686190A1/en active Pending
- 2014-07-10 HU HUE14822106A patent/HUE047782T2/hu unknown
- 2014-07-10 PE PE2016000039A patent/PE20160524A1/es unknown
- 2014-07-10 RS RS20200156A patent/RS59922B1/sr unknown
- 2014-07-10 AU AU2014289744A patent/AU2014289744C1/en active Active
- 2014-07-10 ES ES14822106T patent/ES2773321T3/es active Active
- 2014-07-10 KR KR1020167003499A patent/KR102366734B1/ko active Active
- 2014-07-10 MX MX2016000360A patent/MX369319B/es active IP Right Grant
- 2014-07-10 PT PT148221062T patent/PT3019483T/pt unknown
- 2014-07-10 MY MYPI2019007872A patent/MY196418A/en unknown
- 2014-07-10 MX MX2019013140A patent/MX391858B/es unknown
- 2014-07-10 LT LTEP14822106.2T patent/LT3019483T/lt unknown
- 2014-07-10 PH PH1/2021/551649A patent/PH12021551649A1/en unknown
- 2014-07-10 WO PCT/CN2014/081957 patent/WO2015003640A1/en not_active Ceased
- 2014-07-10 JP JP2016524672A patent/JP6538037B2/ja active Active
- 2014-07-10 KR KR1020227005567A patent/KR102519463B1/ko active Active
- 2014-07-10 MY MYPI2016000020A patent/MY175824A/en unknown
- 2014-07-10 HR HRP20200274TT patent/HRP20200274T1/hr unknown
- 2014-07-10 UA UAA201601119A patent/UA122387C2/uk unknown
- 2014-07-10 SG SG11201600185UA patent/SG11201600185UA/en unknown
- 2014-07-10 SI SI201431492T patent/SI3019483T1/sl unknown
- 2014-07-10 PL PL14822106T patent/PL3019483T3/pl unknown
- 2014-07-10 CA CA2917358A patent/CA2917358C/en active Active
- 2014-07-10 DK DK14822106.2T patent/DK3019483T3/da active
- 2014-07-11 TW TW107138083A patent/TWI756482B/zh active
- 2014-07-11 AR ARP140102587A patent/AR096902A1/es active IP Right Grant
- 2014-07-11 US US14/328,885 patent/US9579324B2/en active Active
- 2014-07-11 TW TW110137062A patent/TWI759251B/zh active
- 2014-07-11 TW TW103123881A patent/TWI692472B/zh active
-
2016
- 2016-01-07 IL IL243494A patent/IL243494B/en active IP Right Grant
- 2016-01-11 PH PH12016500077A patent/PH12016500077B1/en unknown
- 2016-01-11 SA SA516370384A patent/SA516370384B1/ar unknown
- 2016-01-11 SA SA520411465A patent/SA520411465B1/ar unknown
- 2016-01-11 CL CL2016000052A patent/CL2016000052A1/es unknown
- 2016-01-29 ZA ZA2016/00667A patent/ZA201600667B/en unknown
- 2016-02-11 CR CR20160069A patent/CR20160069A/es unknown
- 2016-04-07 US US15/093,345 patent/US10028961B2/en active Active
- 2016-12-28 US US15/392,681 patent/US10172864B2/en active Active
-
2017
- 2017-01-24 ZA ZA2017/00572A patent/ZA201700572B/en unknown
- 2017-03-08 CL CL2017000554A patent/CL2017000554A1/es unknown
-
2018
- 2018-10-23 US US16/167,725 patent/US10946023B2/en active Active
-
2019
- 2019-02-20 AU AU2019201179A patent/AU2019201179B2/en active Active
- 2019-05-30 PH PH12019501197A patent/PH12019501197A1/en unknown
- 2019-06-05 JP JP2019105001A patent/JP2019163326A/ja active Pending
- 2019-06-30 IL IL267743A patent/IL267743B/en unknown
-
2020
- 2020-02-18 CY CY20201100149T patent/CY1122671T1/el unknown
-
2021
- 2021-01-26 US US17/158,867 patent/US11844758B2/en active Active
- 2021-05-25 JP JP2021087457A patent/JP7450581B2/ja active Active
-
2023
- 2023-10-05 US US18/376,981 patent/US12433895B2/en active Active
-
2024
- 2024-01-05 AR ARP240100023A patent/AR131555A2/es unknown
- 2024-03-05 JP JP2024032681A patent/JP2024057088A/ja active Pending
- 2024-04-29 EC ECSENADI202431979A patent/ECSP24031979A/es unknown
-
2026
- 2026-03-04 FR FR26C1011C patent/FR26C1011I1/fr active Active
- 2026-03-04 NO NO2026014C patent/NO2026014I1/no unknown
- 2026-03-04 FI FIC20265008C patent/FIC20265008I1/fi unknown
- 2026-03-05 LT LTPA2026510C patent/LTPA2026510I1/lt unknown
- 2026-03-06 NL NL301370C patent/NL301370I2/nl unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2016526561A5 (https=) | ||
| JP7450581B2 (ja) | 治療活性化合物およびそれらの使用方法 | |
| KR101360621B1 (ko) | 다환식 아미노산 유도체 및 그의 사용 방법 | |
| JP2012517479A5 (https=) | ||
| RU2016110412A (ru) | Некоторые химические соединения, композиции и способы | |
| EA023517B1 (ru) | Модуляторы глюкагонового рецептора | |
| RU2009147733A (ru) | Пиридилпиперидновые антагонисты рецептора орексинов | |
| JP2011500594A5 (https=) | ||
| JP2013510876A5 (https=) | ||
| NZ609955A (en) | Sgc stimulators | |
| JP2010513272A5 (https=) | ||
| CA2432000A1 (en) | Pyrimidineamines as angiogenesis modulators | |
| JP2016523976A5 (https=) | ||
| RU2006126974A (ru) | Амидное производное и лекарственное средство | |
| RU2014117642A (ru) | Способ получения мегакариоцитов и/или тромбоцитов из плюрипотентных стволовых клеток | |
| JP2016523935A5 (https=) | ||
| JP2014531436A5 (https=) | ||
| RU2019123404A (ru) | Производное пиримидина | |
| RU2013130925A (ru) | Оксимовые соединения в качестве средств для повышения уровня холестерина высокой плотности | |
| RU2012147511A (ru) | Применение ингибиторов c-src в комбинации с пиримидиламинобензамидом для лечения лейкоза | |
| RU2005103618A (ru) | Ингибирующие циклооксигеназу-2 (цог-2) производные пиридина | |
| RU2017145929A (ru) | МОДУЛЯТОРЫ ROR ГАММА(RORγ) | |
| JP2020532589A5 (https=) | ||
| CA2387536A1 (en) | Rate-controlled particles | |
| RU2013110324A (ru) | Новые модуляторы trpv3 |