RU2001134899A - Pyrroltriazine kinase inhibitors - Google Patents
Pyrroltriazine kinase inhibitorsInfo
- Publication number
- RU2001134899A RU2001134899A RU2001134899/04A RU2001134899A RU2001134899A RU 2001134899 A RU2001134899 A RU 2001134899A RU 2001134899/04 A RU2001134899/04 A RU 2001134899/04A RU 2001134899 A RU2001134899 A RU 2001134899A RU 2001134899 A RU2001134899 A RU 2001134899A
- Authority
- RU
- Russia
- Prior art keywords
- triazine
- amino
- carboxylic acid
- pyrrolo
- methylpyrrolo
- Prior art date
Links
- 239000003757 phosphotransferase inhibitor Substances 0.000 title 1
- -1 3-hydroxy-4-methylphenyl Chemical group 0.000 claims 58
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 31
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 9
- 239000000203 mixture Substances 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- LCGLNKUTAGEVQW-UHFFFAOYSA-N dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 150000004702 methyl esters Chemical class 0.000 claims 5
- 125000003107 substituted aryl group Chemical group 0.000 claims 5
- RDOXTESZEPMUJZ-UHFFFAOYSA-N Anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 230000000694 effects Effects 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims 3
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims 3
- 239000004202 carbamide Substances 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- NFILHPVBZNKVNP-UHFFFAOYSA-N ethyl 4,6-dichloro-3-formyl-1H-indole-2-carboxylate Chemical compound ClC1=CC(Cl)=C2C(C=O)=C(C(=O)OCC)NC2=C1 NFILHPVBZNKVNP-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 230000002401 inhibitory effect Effects 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- WNWVKZTYMQWFHE-UHFFFAOYSA-N 4-ethylmorpholine Chemical group [CH2]CN1CCOCC1 WNWVKZTYMQWFHE-UHFFFAOYSA-N 0.000 claims 2
- 206010003816 Autoimmune disease Diseases 0.000 claims 2
- 102000009465 Growth Factor Receptors Human genes 0.000 claims 2
- 108010009202 Growth Factor Receptors Proteins 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 239000002246 antineoplastic agent Substances 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbamate Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 2
- 239000002254 cytotoxic agent Substances 0.000 claims 2
- 231100000599 cytotoxic agent Toxicity 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- BLAYJEOQFIIFQQ-UHFFFAOYSA-N methyl 1,2,4-triazine-6-carboxylate Chemical compound COC(=O)C1=CN=CN=N1 BLAYJEOQFIIFQQ-UHFFFAOYSA-N 0.000 claims 2
- XFQMHQALFSWUAC-UHFFFAOYSA-N methyl 4-[5-(methanesulfonamido)-2-oxo-1,3-dihydroindol-3-yl]-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound O=C1NC2=CC=C(NS(C)(=O)=O)C=C2C1C1=NC=NN2C=C(C(=O)OC)C(C)=C21 XFQMHQALFSWUAC-UHFFFAOYSA-N 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 230000002062 proliferating Effects 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000011780 sodium chloride Substances 0.000 claims 2
- CFCUWKMKBJTWLW-BGLFSJPPSA-N (2S,3S)-2-[(2S,4R,5R,6R)-4-[(2S,4R,5R,6R)-4-[(2S,4S,5R,6R)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-3-[(1S,3S,4R)-3,4-dihydroxy-1-methoxy-2-oxopentyl]-6-[(2S,4R,5S,6R)-4-[(2S,4R,5S,6R)-4,5-dih Chemical compound O([C@@H]1C[C@@H](O[C@H](C)[C@@H]1O)OC=1C=C2C=C3C[C@H]([C@@H](C(=O)C3=C(O)C2=C(O)C=1C)O[C@@H]1O[C@H](C)[C@@H](O)[C@H](O[C@@H]2O[C@H](C)[C@@H](O)[C@H](O[C@@H]3O[C@H](C)[C@@H](O)[C@@](C)(O)C3)C2)C1)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)[C@H]1C[C@@H](O)[C@H](O)[C@@H](C)O1 CFCUWKMKBJTWLW-BGLFSJPPSA-N 0.000 claims 1
- XOZIUKBZLSUILX-GIQCAXHBSA-N (4S,7R,8S,9S,13Z,16S)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione Chemical compound O1C(=O)C[C@H](O)C(C)(C)C(=O)[C@H](C)[C@@H](O)[C@@H](C)CCC\C(C)=C/C[C@H]1C(\C)=C\C1=CSC(C)=N1 XOZIUKBZLSUILX-GIQCAXHBSA-N 0.000 claims 1
- NRUKOCRGYNPUPR-QBPJDGROSA-N (5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-thiophen-2-yl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 claims 1
- COVZYZSDYWQREU-UHFFFAOYSA-N 1,4-Butanediol, dimethanesulfonate Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims 1
- NPIISCWCOBHJGF-UHFFFAOYSA-N 1-[6-(pyrrolo[2,1-f][1,2,4]triazin-4-ylamino)-2,3-dihydroindol-1-yl]ethanone Chemical compound C1=NN2C=CC=C2C(NC2=CC=C3CCN(C3=C2)C(=O)C)=N1 NPIISCWCOBHJGF-UHFFFAOYSA-N 0.000 claims 1
- QOUDIMIOLOWYDU-UHFFFAOYSA-N 2-hydroxy-4-[(6-methoxycarbonyl-5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yl)amino]benzoic acid Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC1=CC=C(C(O)=O)C(O)=C1 QOUDIMIOLOWYDU-UHFFFAOYSA-N 0.000 claims 1
- QWKFRPBJBADCAF-UHFFFAOYSA-N 2-hydroxy-5-[(6-methoxycarbonyl-5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yl)amino]benzoic acid Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC1=CC=C(O)C(C(O)=O)=C1 QWKFRPBJBADCAF-UHFFFAOYSA-N 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- QVHFAUADDZADAN-UHFFFAOYSA-N 2-methyl-5-(pyrrolo[2,1-f][1,2,4]triazin-4-ylamino)phenol Chemical compound C1=C(O)C(C)=CC=C1NC1=NC=NN2C1=CC=C2 QVHFAUADDZADAN-UHFFFAOYSA-N 0.000 claims 1
- ATRMGRIXDIZXRO-UHFFFAOYSA-N 2-methyl-5-[(5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yl)amino]phenol Chemical compound C12=C(C)C=CN2N=CN=C1NC1=CC=C(C)C(O)=C1 ATRMGRIXDIZXRO-UHFFFAOYSA-N 0.000 claims 1
- BNJHLXRPLVJJDL-UHFFFAOYSA-N 2-methyl-5-[(6-methylpyrrolo[2,1-f][1,2,4]triazin-4-yl)amino]phenol Chemical compound N=1C=NN2C=C(C)C=C2C=1NC1=CC=C(C)C(O)=C1 BNJHLXRPLVJJDL-UHFFFAOYSA-N 0.000 claims 1
- QFAYCQKPUDKQJB-UHFFFAOYSA-N 2-methyl-5-[(7-methylpyrrolo[2,1-f][1,2,4]triazin-4-yl)amino]phenol Chemical compound N=1C=NN2C(C)=CC=C2C=1NC1=CC=C(C)C(O)=C1 QFAYCQKPUDKQJB-UHFFFAOYSA-N 0.000 claims 1
- QYRNAEKFMGWIGG-UHFFFAOYSA-N 2-methyl-5-[[5-methyl-6-[3-(triazol-2-yl)propoxy]pyrrolo[2,1-f][1,2,4]triazin-4-yl]amino]phenol Chemical compound C=1N2N=CN=C(NC=3C=C(O)C(C)=CC=3)C2=C(C)C=1OCCCN1N=CC=N1 QYRNAEKFMGWIGG-UHFFFAOYSA-N 0.000 claims 1
- LYYDMOGYPIFQMC-UHFFFAOYSA-N 2-methyl-N-[5-methyl-4-(2-oxo-1,3-dihydroindol-3-yl)pyrrolo[2,1-f][1,2,4]triazin-6-yl]propanamide Chemical compound O=C1NC2=CC=CC=C2C1C1=NC=NN2C=C(NC(=O)C(C)C)C(C)=C21 LYYDMOGYPIFQMC-UHFFFAOYSA-N 0.000 claims 1
- JWPIMONRZARAIM-UHFFFAOYSA-N 3-(6-amino-5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yl)-1,3-dihydroindol-2-one Chemical compound O=C1NC2=CC=CC=C2C1C1=NC=NN2C=C(N)C(C)=C12 JWPIMONRZARAIM-UHFFFAOYSA-N 0.000 claims 1
- XADKGZIXOCUEGH-UHFFFAOYSA-N 3-[(6-methoxycarbonyl-5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yl)amino]benzenesulfonic acid Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC1=CC=CC(S(O)(=O)=O)=C1 XADKGZIXOCUEGH-UHFFFAOYSA-N 0.000 claims 1
- SSFNNFZQSCHTQA-UHFFFAOYSA-N 3-[(6-methoxycarbonyl-5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yl)amino]benzoic acid Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC1=CC=CC(C(O)=O)=C1 SSFNNFZQSCHTQA-UHFFFAOYSA-N 0.000 claims 1
- ZBBJKMQQUJNSPU-UHFFFAOYSA-N 3-[5-methoxy-6-(4-morpholin-4-ylbutylamino)pyrrolo[2,1-f][1,2,4]triazin-4-yl]-1,3-dihydroindol-2-one Chemical compound C=1N2N=CN=C(C3C4=CC=CC=C4NC3=O)C2=C(OC)C=1NCCCCN1CCOCC1 ZBBJKMQQUJNSPU-UHFFFAOYSA-N 0.000 claims 1
- UBEBWXMRDPAVIQ-UHFFFAOYSA-N 3-[5-methoxy-6-[4-(4-methylpiperazin-1-yl)butylamino]pyrrolo[2,1-f][1,2,4]triazin-4-yl]-1,3-dihydroindol-2-one Chemical compound C=1N2N=CN=C(C3C4=CC=CC=C4NC3=O)C2=C(OC)C=1NCCCCN1CCN(C)CC1 UBEBWXMRDPAVIQ-UHFFFAOYSA-N 0.000 claims 1
- ZGOADNFNATWGMR-UHFFFAOYSA-N 3-[5-methyl-6-(3-morpholin-4-yl-3-oxopropyl)pyrrolo[2,1-f][1,2,4]triazin-4-yl]-1,3-dihydroindol-2-one Chemical compound C=1N2N=CN=C(C3C4=CC=CC=C4NC3=O)C2=C(C)C=1CCC(=O)N1CCOCC1 ZGOADNFNATWGMR-UHFFFAOYSA-N 0.000 claims 1
- XGDZJYDCZVXFOW-UHFFFAOYSA-N 3-[5-methyl-6-[2-(1,2,4-triazol-1-yl)ethoxy]pyrrolo[2,1-f][1,2,4]triazin-4-yl]-1,3-dihydroindol-2-one Chemical compound C=1N2N=CN=C(C3C4=CC=CC=C4NC3=O)C2=C(C)C=1OCCN1C=NC=N1 XGDZJYDCZVXFOW-UHFFFAOYSA-N 0.000 claims 1
- YHASGHHGYLHBOM-UHFFFAOYSA-N 3-[5-methyl-6-[3-(1,2,4-triazol-1-yl)propoxy]pyrrolo[2,1-f][1,2,4]triazin-4-yl]-1,3-dihydroindol-2-one Chemical compound C=1N2N=CN=C(C3C4=CC=CC=C4NC3=O)C2=C(C)C=1OCCCN1C=NC=N1 YHASGHHGYLHBOM-UHFFFAOYSA-N 0.000 claims 1
- NHOXNBJEWCXHFU-UHFFFAOYSA-N 3-[5-methyl-6-[3-(4-methylpiperazin-1-yl)-3-oxopropyl]pyrrolo[2,1-f][1,2,4]triazin-4-yl]-1,3-dihydroindol-2-one Chemical compound C1CN(C)CCN1C(=O)CCC1=CN(N=CN=C2C3C4=CC=CC=C4NC3=O)C2=C1C NHOXNBJEWCXHFU-UHFFFAOYSA-N 0.000 claims 1
- FLROJJGKUKLCAE-UHFFFAOYSA-N 3-amino-2-methylphenol Chemical compound CC1=C(N)C=CC=C1O FLROJJGKUKLCAE-UHFFFAOYSA-N 0.000 claims 1
- LFRGUQOMDVBCQH-UHFFFAOYSA-N 4-(1H-indazol-6-ylamino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid Chemical compound C1=C2C=NNC2=CC(NC2=NC=NN3C=C(C(=C23)C)C(O)=O)=C1 LFRGUQOMDVBCQH-UHFFFAOYSA-N 0.000 claims 1
- NOBMPTSPMNQKBV-UHFFFAOYSA-N 4-(2-oxo-1,3-dihydroindol-3-yl)pyrrolo[2,1-f][1,2,4]triazine-5,6-dicarboxylic acid Chemical compound O=C1NC2=CC=CC=C2C1C1=NC=NN2C=C(C(=O)O)C(C(O)=O)=C21 NOBMPTSPMNQKBV-UHFFFAOYSA-N 0.000 claims 1
- KNBCTKMWYMAHKB-UHFFFAOYSA-N 4-(3-hydroxy-4-methylanilino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid Chemical compound C12=C(C)C(C(O)=O)=CN2N=CN=C1NC1=CC=C(C)C(O)=C1 KNBCTKMWYMAHKB-UHFFFAOYSA-N 0.000 claims 1
- RWCFRRIJDJBQND-UHFFFAOYSA-N 4-(3-hydroxy-4-methylanilino)-N,5-dimethylpyrrolo[2,1-f][1,2,4]triazine-6-carboxamide Chemical compound C12=C(C)C(C(=O)NC)=CN2N=CN=C1NC1=CC=C(C)C(O)=C1 RWCFRRIJDJBQND-UHFFFAOYSA-N 0.000 claims 1
- JDAIVEQWIJZUDL-UHFFFAOYSA-N 4-(3-hydroxy-4-methylanilino)-N-(3-methoxypropyl)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxamide Chemical compound C12=C(C)C(C(=O)NCCCOC)=CN2N=CN=C1NC1=CC=C(C)C(O)=C1 JDAIVEQWIJZUDL-UHFFFAOYSA-N 0.000 claims 1
- TWADJUPZVIGCJH-UHFFFAOYSA-N 4-(3-hydroxy-4-methylanilino)-N-(3-morpholin-4-ylpropyl)-5-propylpyrrolo[2,1-f][1,2,4]triazine-6-carboxamide Chemical compound C12=C(CCC)C(C(=O)NCCCN3CCOCC3)=CN2N=CN=C1NC1=CC=C(C)C(O)=C1 TWADJUPZVIGCJH-UHFFFAOYSA-N 0.000 claims 1
- ACOVWOHMXFTDJN-UHFFFAOYSA-N 4-(5-fluoro-2-oxo-1,3-dihydroindol-3-yl)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid Chemical compound O=C1NC2=CC=C(F)C=C2C1C1=NC=NN2C=C(C(O)=O)C(C)=C12 ACOVWOHMXFTDJN-UHFFFAOYSA-N 0.000 claims 1
- UBEUEPPIGJRBFK-UHFFFAOYSA-N 4-(6-cyano-2-oxo-1,3-dihydroindol-3-yl)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid Chemical compound O=C1NC2=CC(C#N)=CC=C2C1C1=NC=NN2C=C(C(O)=O)C(C)=C12 UBEUEPPIGJRBFK-UHFFFAOYSA-N 0.000 claims 1
- RIRPTJAQAUIJHD-UHFFFAOYSA-N 4-[(1-benzylindazol-5-yl)amino]-5-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid Chemical compound C12=C(C(C)C)C(C(O)=O)=CN2N=CN=C1NC(C=C1C=N2)=CC=C1N2CC1=CC=CC=C1 RIRPTJAQAUIJHD-UHFFFAOYSA-N 0.000 claims 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- NSSREJILCYZENK-UHFFFAOYSA-N 5-[(5,6-dimethylpyrrolo[2,1-f][1,2,4]triazin-4-yl)amino]-2-methylphenol Chemical compound C12=C(C)C(C)=CN2N=CN=C1NC1=CC=C(C)C(O)=C1 NSSREJILCYZENK-UHFFFAOYSA-N 0.000 claims 1
- FLYWWNDDXORVRE-UHFFFAOYSA-N 5-[(5,7-dimethylpyrrolo[2,1-f][1,2,4]triazin-4-yl)amino]-2-methylphenol Chemical compound C12=C(C)C=C(C)N2N=CN=C1NC1=CC=C(C)C(O)=C1 FLYWWNDDXORVRE-UHFFFAOYSA-N 0.000 claims 1
- KNVIJRHUKKOQEA-UHFFFAOYSA-N 5-[(5-ethylpyrrolo[2,1-f][1,2,4]triazin-4-yl)amino]-2-methylphenol Chemical compound C12=C(CC)C=CN2N=CN=C1NC1=CC=C(C)C(O)=C1 KNVIJRHUKKOQEA-UHFFFAOYSA-N 0.000 claims 1
- BIMDIEZNVGZTCY-UHFFFAOYSA-N 5-[(6-amino-5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yl)amino]-2-methylphenol Chemical compound C12=C(C)C(N)=CN2N=CN=C1NC1=CC=C(C)C(O)=C1 BIMDIEZNVGZTCY-UHFFFAOYSA-N 0.000 claims 1
- WQLIOGMNMDBAAX-UHFFFAOYSA-N 5-[(6-ethyl-5,7-dimethylpyrrolo[2,1-f][1,2,4]triazin-4-yl)amino]-2-methylphenol Chemical compound N=1C=NN2C(C)=C(CC)C(C)=C2C=1NC1=CC=C(C)C(O)=C1 WQLIOGMNMDBAAX-UHFFFAOYSA-N 0.000 claims 1
- OYWONCFUNIWAQD-UHFFFAOYSA-N 5-[[2-(dimethylamino)pyrrolo[2,1-f][1,2,4]triazin-4-yl]amino]-2-methylphenol Chemical compound C12=CC=CN2N=C(N(C)C)N=C1NC1=CC=C(C)C(O)=C1 OYWONCFUNIWAQD-UHFFFAOYSA-N 0.000 claims 1
- FTGMAZNZVBHTAD-UHFFFAOYSA-N 5-[[6-(hydroxymethyl)-5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yl]amino]-2-methylphenol Chemical compound C12=C(C)C(CO)=CN2N=CN=C1NC1=CC=C(C)C(O)=C1 FTGMAZNZVBHTAD-UHFFFAOYSA-N 0.000 claims 1
- SSEICAMCKGJKRN-UHFFFAOYSA-N 5-ethyl-4-[(6-methoxypyridin-3-yl)amino]pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid Chemical compound C12=C(CC)C(C(O)=O)=CN2N=CN=C1NC1=CC=C(OC)N=C1 SSEICAMCKGJKRN-UHFFFAOYSA-N 0.000 claims 1
- GHASVSINZRGABV-UHFFFAOYSA-N 5-flurouricil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims 1
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- 125000005418 aryl aryl group Chemical group 0.000 claims 1
- DVQHYTBCTGYNNN-UHFFFAOYSA-N azane;cyclobutane-1,1-dicarboxylic acid;platinum Chemical compound N.N.[Pt].OC(=O)C1(C(O)=O)CCC1 DVQHYTBCTGYNNN-UHFFFAOYSA-N 0.000 claims 1
- SDPZKXVWIGGJLK-UHFFFAOYSA-N benzyl N-[5-ethyl-4-[(6-methoxypyridin-3-yl)amino]pyrrolo[2,1-f][1,2,4]triazin-6-yl]carbamate Chemical compound C=1N2N=CN=C(NC=3C=NC(OC)=CC=3)C2=C(CC)C=1NC(=O)OCC1=CC=CC=C1 SDPZKXVWIGGJLK-UHFFFAOYSA-N 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 229960002092 busulfan Drugs 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229960004316 cisplatin Drugs 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 229960003668 docetaxel Drugs 0.000 claims 1
- 229930013356 epothilones Natural products 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- WHADXHLLRBBLRM-UHFFFAOYSA-N ethyl 4-(3,4-dihydro-1H-isoquinolin-2-yl)-5-ethylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C1CC2=CC=CC=C2CN1C1=NC=NN2C=C(C(=O)OCC)C(CC)=C21 WHADXHLLRBBLRM-UHFFFAOYSA-N 0.000 claims 1
- WBUUAEHGIKTMDW-UHFFFAOYSA-N ethyl 4-(3,4-dihydro-2H-quinolin-1-yl)-5-ethylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C1CCC2=CC=CC=C2N1C1=NC=NN2C=C(C(=O)OCC)C(CC)=C21 WBUUAEHGIKTMDW-UHFFFAOYSA-N 0.000 claims 1
- ZCKGARDCKJFLRH-UHFFFAOYSA-N ethyl 4-(3-bromoanilino)-5-ethylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(CC)C(C(=O)OCC)=CN2N=CN=C1NC1=CC=CC(Br)=C1 ZCKGARDCKJFLRH-UHFFFAOYSA-N 0.000 claims 1
- DCVODVBLQRXBMG-UHFFFAOYSA-N ethyl 4-(3-chloro-4-fluoroanilino)-5-ethylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(CC)C(C(=O)OCC)=CN2N=CN=C1NC1=CC=C(F)C(Cl)=C1 DCVODVBLQRXBMG-UHFFFAOYSA-N 0.000 claims 1
- LGLWDJYPRLNVEM-UHFFFAOYSA-N ethyl 4-(3-hydroxy-4-methylanilino)-5-methoxypyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(OC)C(C(=O)OCC)=CN2N=CN=C1NC1=CC=C(C)C(O)=C1 LGLWDJYPRLNVEM-UHFFFAOYSA-N 0.000 claims 1
- AQOVLSUINZASEY-UHFFFAOYSA-N ethyl 4-(3-hydroxy-4-methylanilino)-5-phenylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C=3C=CC=CC=3)C(C(=O)OCC)=CN2N=CN=C1NC1=CC=C(C)C(O)=C1 AQOVLSUINZASEY-UHFFFAOYSA-N 0.000 claims 1
- MKTNMOUKLPKCQG-UHFFFAOYSA-N ethyl 4-(3-hydroxy-4-methylanilino)-5-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C(C)C)C(C(=O)OCC)=CN2N=CN=C1NC1=CC=C(C)C(O)=C1 MKTNMOUKLPKCQG-UHFFFAOYSA-N 0.000 claims 1
- LPNBNAQAHDDXSW-UHFFFAOYSA-N ethyl 4-(3-hydroxy-4-methylanilino)-5-propylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(CCC)C(C(=O)OCC)=CN2N=CN=C1NC1=CC=C(C)C(O)=C1 LPNBNAQAHDDXSW-UHFFFAOYSA-N 0.000 claims 1
- UUQGIFBMQJPEQA-UHFFFAOYSA-N ethyl 4-(4-bromo-2-fluoroanilino)-5-methoxypyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(OC)C(C(=O)OCC)=CN2N=CN=C1NC1=CC=C(Br)C=C1F UUQGIFBMQJPEQA-UHFFFAOYSA-N 0.000 claims 1
- JVTHYYYQGGDVNO-UHFFFAOYSA-N ethyl 4-(4-bromoanilino)-5-ethylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(CC)C(C(=O)OCC)=CN2N=CN=C1NC1=CC=C(Br)C=C1 JVTHYYYQGGDVNO-UHFFFAOYSA-N 0.000 claims 1
- FKTDPTZOFGBLDH-UHFFFAOYSA-N ethyl 4-(benzylamino)-5-ethylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(CC)C(C(=O)OCC)=CN2N=CN=C1NCC1=CC=CC=C1 FKTDPTZOFGBLDH-UHFFFAOYSA-N 0.000 claims 1
- TZLBLRKRBRAYOL-UHFFFAOYSA-N ethyl 4-(butylamino)-5-ethylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound CCCCNC1=NC=NN2C=C(C(=O)OCC)C(CC)=C12 TZLBLRKRBRAYOL-UHFFFAOYSA-N 0.000 claims 1
- QSJBBGOHKRYXKH-UHFFFAOYSA-N ethyl 4-(cyclohexylmethylamino)-5-ethylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(CC)C(C(=O)OCC)=CN2N=CN=C1NCC1CCCCC1 QSJBBGOHKRYXKH-UHFFFAOYSA-N 0.000 claims 1
- QVZVMXGTYYWUFV-UHFFFAOYSA-N ethyl 4-[(1-benzylindazol-4-yl)amino]-5-ethylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(CC)C(C(=O)OCC)=CN2N=CN=C1NC(C=1C=N2)=CC=CC=1N2CC1=CC=CC=C1 QVZVMXGTYYWUFV-UHFFFAOYSA-N 0.000 claims 1
- DLQGOUYSCARQKO-UHFFFAOYSA-N ethyl 4-[(1-benzylindazol-5-yl)amino]-5-ethylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(CC)C(C(=O)OCC)=CN2N=CN=C1NC(C=C1C=N2)=CC=C1N2CC1=CC=CC=C1 DLQGOUYSCARQKO-UHFFFAOYSA-N 0.000 claims 1
- VRGOWRHHJHLAFC-UHFFFAOYSA-N ethyl 4-[(1-benzylindazol-5-yl)amino]-5-propylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(CCC)C(C(=O)OCC)=CN2N=CN=C1NC(C=C1C=N2)=CC=C1N2CC1=CC=CC=C1 VRGOWRHHJHLAFC-UHFFFAOYSA-N 0.000 claims 1
- WKNMCKTVXYANAJ-UHFFFAOYSA-N ethyl 4-[(3-chloro-4-fluorophenyl)methyl]-5-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C(C)C)C(C(=O)OCC)=CN2N=CN=C1CC1=CC=C(F)C(Cl)=C1 WKNMCKTVXYANAJ-UHFFFAOYSA-N 0.000 claims 1
- LHNLSKWJYGRCPC-UHFFFAOYSA-N ethyl 4-[(4-bromophenyl)methylamino]-5-ethylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(CC)C(C(=O)OCC)=CN2N=CN=C1NCC1=CC=C(Br)C=C1 LHNLSKWJYGRCPC-UHFFFAOYSA-N 0.000 claims 1
- NSVYODQZBAKEGH-UHFFFAOYSA-N ethyl 4-[(4-cyanocyclohexyl)methylamino]-5-ethylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(CC)C(C(=O)OCC)=CN2N=CN=C1NCC1CCC(C#N)CC1 NSVYODQZBAKEGH-UHFFFAOYSA-N 0.000 claims 1
- ZTOVINQRRLDIIS-UHFFFAOYSA-N ethyl 4-[(6-methoxypyridin-3-yl)amino]-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OCC)=CN2N=CN=C1NC1=CC=C(OC)N=C1 ZTOVINQRRLDIIS-UHFFFAOYSA-N 0.000 claims 1
- QAMAVCQMYQCHAK-UHFFFAOYSA-N ethyl 4-anilino-5-ethylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(CC)C(C(=O)OCC)=CN2N=CN=C1NC1=CC=CC=C1 QAMAVCQMYQCHAK-UHFFFAOYSA-N 0.000 claims 1
- ZJHZBQMSMSBKSE-UHFFFAOYSA-N ethyl 5-benzyl-4-(3-chloro-4-fluoroanilino)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(CC=3C=CC=CC=3)C(C(=O)OCC)=CN2N=CN=C1NC1=CC=C(F)C(Cl)=C1 ZJHZBQMSMSBKSE-UHFFFAOYSA-N 0.000 claims 1
- KFIAKLFWWRYIIL-UHFFFAOYSA-N ethyl 5-benzyl-4-(3-hydroxy-4-methylanilino)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(CC=3C=CC=CC=3)C(C(=O)OCC)=CN2N=CN=C1NC1=CC=C(C)C(O)=C1 KFIAKLFWWRYIIL-UHFFFAOYSA-N 0.000 claims 1
- MVZAPDAYTFZUSI-UHFFFAOYSA-N ethyl 5-benzyl-4-[(1-benzylindazol-5-yl)amino]pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(CC=3C=CC=CC=3)C(C(=O)OCC)=CN2N=CN=C1NC(C=C1C=N2)=CC=C1N2CC1=CC=CC=C1 MVZAPDAYTFZUSI-UHFFFAOYSA-N 0.000 claims 1
- SQLZRYUJCRVACR-UHFFFAOYSA-N ethyl 5-ethoxy-4-(2-oxo-1,3-dihydroindol-3-yl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound O=C1NC2=CC=CC=C2C1C1=NC=NN2C=C(C(=O)OCC)C(OCC)=C21 SQLZRYUJCRVACR-UHFFFAOYSA-N 0.000 claims 1
- KBNYAHIDLSFPOR-UHFFFAOYSA-N ethyl 5-ethoxy-4-(3-hydroxy-4-methylanilino)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(OCC)C(C(=O)OCC)=CN2N=CN=C1NC1=CC=C(C)C(O)=C1 KBNYAHIDLSFPOR-UHFFFAOYSA-N 0.000 claims 1
- JLRNNJCMROTZGX-UHFFFAOYSA-N ethyl 5-ethyl-4-(1H-indazol-6-ylamino)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C1=C2C=NNC2=CC(NC2=NC=NN3C=C(C(=C32)CC)C(=O)OCC)=C1 JLRNNJCMROTZGX-UHFFFAOYSA-N 0.000 claims 1
- OQOXJBVVGBWCDS-UHFFFAOYSA-N ethyl 5-ethyl-4-(2-methoxyethylamino)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound N1=CN=C(NCCOC)C2=C(CC)C(C(=O)OCC)=CN21 OQOXJBVVGBWCDS-UHFFFAOYSA-N 0.000 claims 1
- NQZYJVINZHXZMK-UHFFFAOYSA-N ethyl 5-ethyl-4-(2-phenylethylamino)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(CC)C(C(=O)OCC)=CN2N=CN=C1NCCC1=CC=CC=C1 NQZYJVINZHXZMK-UHFFFAOYSA-N 0.000 claims 1
- QCROBTKWHAJCOW-UHFFFAOYSA-N ethyl 5-ethyl-4-(2-pyridin-2-ylethylamino)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(CC)C(C(=O)OCC)=CN2N=CN=C1NCCC1=CC=CC=N1 QCROBTKWHAJCOW-UHFFFAOYSA-N 0.000 claims 1
- VPJQAWXLRDNIOY-UHFFFAOYSA-N ethyl 5-ethyl-4-(3-hydroxy-4-methylanilino)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(CC)C(C(=O)OCC)=CN2N=CN=C1NC1=CC=C(C)C(O)=C1 VPJQAWXLRDNIOY-UHFFFAOYSA-N 0.000 claims 1
- WRSMVQYIQPKKKQ-UHFFFAOYSA-N ethyl 5-ethyl-4-(3-imidazol-1-ylpropylamino)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(CC)C(C(=O)OCC)=CN2N=CN=C1NCCCN1C=CN=C1 WRSMVQYIQPKKKQ-UHFFFAOYSA-N 0.000 claims 1
- HYOYJSGEYGAFEY-UHFFFAOYSA-N ethyl 5-ethyl-4-(4-hydroxyanilino)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(CC)C(C(=O)OCC)=CN2N=CN=C1NC1=CC=C(O)C=C1 HYOYJSGEYGAFEY-UHFFFAOYSA-N 0.000 claims 1
- RWKPDEKRLJTWNV-UHFFFAOYSA-N ethyl 5-ethyl-4-(4-methoxyanilino)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(CC)C(C(=O)OCC)=CN2N=CN=C1NC1=CC=C(OC)C=C1 RWKPDEKRLJTWNV-UHFFFAOYSA-N 0.000 claims 1
- SXUTWMUWKOLBDA-UHFFFAOYSA-N ethyl 5-ethyl-4-(4-phenoxyanilino)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(CC)C(C(=O)OCC)=CN2N=CN=C1NC(C=C1)=CC=C1OC1=CC=CC=C1 SXUTWMUWKOLBDA-UHFFFAOYSA-N 0.000 claims 1
- HSABUOAGWDLQKB-UHFFFAOYSA-N ethyl 5-ethyl-4-(N-methylanilino)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(CC)C(C(=O)OCC)=CN2N=CN=C1N(C)C1=CC=CC=C1 HSABUOAGWDLQKB-UHFFFAOYSA-N 0.000 claims 1
- XCQDPYJEWKGTIW-UHFFFAOYSA-N ethyl 5-ethyl-4-[(1-hydroxycyclohexyl)methylamino]pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(CC)C(C(=O)OCC)=CN2N=CN=C1NCC1(O)CCCCC1 XCQDPYJEWKGTIW-UHFFFAOYSA-N 0.000 claims 1
- LNPPOAXMBAPSIN-UHFFFAOYSA-N ethyl 5-ethyl-4-[(6-methoxypyridin-3-yl)amino]pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(CC)C(C(=O)OCC)=CN2N=CN=C1NC1=CC=C(OC)N=C1 LNPPOAXMBAPSIN-UHFFFAOYSA-N 0.000 claims 1
- OKYDIKYNMQSXSY-UHFFFAOYSA-N ethyl 5-ethyl-4-[3-(methanesulfonamido)-4-methylanilino]pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(CC)C(C(=O)OCC)=CN2N=CN=C1NC1=CC=C(C)C(NS(C)(=O)=O)=C1 OKYDIKYNMQSXSY-UHFFFAOYSA-N 0.000 claims 1
- IKFNDVGENZZACI-CYBMUJFWSA-N ethyl 5-ethyl-4-[[(1R)-1-phenylethyl]amino]pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C1([C@@H](C)NC2=NC=NN3C=C(C(=C32)CC)C(=O)OCC)=CC=CC=C1 IKFNDVGENZZACI-CYBMUJFWSA-N 0.000 claims 1
- IKFNDVGENZZACI-ZDUSSCGKSA-N ethyl 5-ethyl-4-[[(1S)-1-phenylethyl]amino]pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C1([C@H](C)NC2=NC=NN3C=C(C(=C32)CC)C(=O)OCC)=CC=CC=C1 IKFNDVGENZZACI-ZDUSSCGKSA-N 0.000 claims 1
- LQUCEAAOKJQHLM-UHFFFAOYSA-N ethyl 5-ethyl-4-morpholin-4-ylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(CC)C(C(=O)OCC)=CN2N=CN=C1N1CCOCC1 LQUCEAAOKJQHLM-UHFFFAOYSA-N 0.000 claims 1
- WLWRWKLPBOHPRF-UHFFFAOYSA-N ethyl 5-methoxy-4-(2-oxo-1,3-dihydroindol-3-yl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound O=C1NC2=CC=CC=C2C1C1=NC=NN2C=C(C(=O)OCC)C(OC)=C21 WLWRWKLPBOHPRF-UHFFFAOYSA-N 0.000 claims 1
- DZFAYRAOTGSFBC-UHFFFAOYSA-N ethyl 5-methoxy-4-[(6-methoxypyridin-3-yl)amino]pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(OC)C(C(=O)OCC)=CN2N=CN=C1NC1=CC=C(OC)N=C1 DZFAYRAOTGSFBC-UHFFFAOYSA-N 0.000 claims 1
- RBQPHKXLBOYQFO-UHFFFAOYSA-N ethyl 5-methoxy-4-oxo-1H-pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound N1=CN=C(O)C2=C(OC)C(C(=O)OCC)=CN21 RBQPHKXLBOYQFO-UHFFFAOYSA-N 0.000 claims 1
- 229960000255 exemestane Drugs 0.000 claims 1
- 229960004039 finasteride Drugs 0.000 claims 1
- 229960002074 flutamide Drugs 0.000 claims 1
- 239000003102 growth factor Substances 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 229960004768 irinotecan Drugs 0.000 claims 1
- 229960003881 letrozole Drugs 0.000 claims 1
- 229960000485 methotrexate Drugs 0.000 claims 1
- CPPIXUWCTAJFMS-UHFFFAOYSA-N methyl 3-[5-methyl-4-(2-oxo-1,3-dihydroindol-3-yl)pyrrolo[2,1-f][1,2,4]triazin-6-yl]propanoate Chemical compound O=C1NC2=CC=CC=C2C1C1=NC=NN2C=C(CCC(=O)OC)C(C)=C21 CPPIXUWCTAJFMS-UHFFFAOYSA-N 0.000 claims 1
- GZOLPVDOLYQBMB-UHFFFAOYSA-N methyl 4-(1H-indol-6-ylamino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C1=C2C=CNC2=CC(NC2=NC=NN3C=C(C(=C32)C)C(=O)OC)=C1 GZOLPVDOLYQBMB-UHFFFAOYSA-N 0.000 claims 1
- CRIXUQMXXYMARY-UHFFFAOYSA-N methyl 4-(2,3-dihydro-1H-indol-6-ylamino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C1=C2CCNC2=CC(NC2=NC=NN3C=C(C(=C32)C)C(=O)OC)=C1 CRIXUQMXXYMARY-UHFFFAOYSA-N 0.000 claims 1
- KEDFQSCEPKFXHI-UHFFFAOYSA-N methyl 4-(2,3-dihydroindol-1-yl)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C1CC2=CC=CC=C2N1C1=NC=NN2C=C(C(=O)OC)C(C)=C21 KEDFQSCEPKFXHI-UHFFFAOYSA-N 0.000 claims 1
- AGAAWXGEIGAJBE-UHFFFAOYSA-N methyl 4-(2-oxo-1,3-dihydroindol-3-yl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound O=C1NC2=CC=CC=C2C1C1=NC=NN2C1=CC(C(=O)OC)=C2 AGAAWXGEIGAJBE-UHFFFAOYSA-N 0.000 claims 1
- FFOHMEIHKYAANS-UHFFFAOYSA-N methyl 4-(2H-benzotriazol-5-ylamino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C1=C2NN=NC2=CC(NC2=NC=NN3C=C(C(=C32)C)C(=O)OC)=C1 FFOHMEIHKYAANS-UHFFFAOYSA-N 0.000 claims 1
- UEMMUOLAXAGUOE-UHFFFAOYSA-N methyl 4-(3,4-dimethoxyanilino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC1=CC=C(OC)C(OC)=C1 UEMMUOLAXAGUOE-UHFFFAOYSA-N 0.000 claims 1
- JMSXXXONKQOXOT-UHFFFAOYSA-N methyl 4-(3,4-dimethylanilino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC1=CC=C(C)C(C)=C1 JMSXXXONKQOXOT-UHFFFAOYSA-N 0.000 claims 1
- CJHLDECNXNRHRZ-UHFFFAOYSA-N methyl 4-(3-amino-4-methylanilino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC1=CC=C(C)C(N)=C1 CJHLDECNXNRHRZ-UHFFFAOYSA-N 0.000 claims 1
- AQCROJDWLBTFHG-UHFFFAOYSA-N methyl 4-(3-chloro-4-fluoroanilino)-5-(3-phenylmethoxypropyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(CCCOCC=3C=CC=CC=3)C(C(=O)OC)=CN2N=CN=C1NC1=CC=C(F)C(Cl)=C1 AQCROJDWLBTFHG-UHFFFAOYSA-N 0.000 claims 1
- DTQZNYIRCFAEAW-UHFFFAOYSA-N methyl 4-(3-chloro-4-fluoroanilino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC1=CC=C(F)C(Cl)=C1 DTQZNYIRCFAEAW-UHFFFAOYSA-N 0.000 claims 1
- QRLJHZCWMRXNAP-UHFFFAOYSA-N methyl 4-(3-chloro-4-fluoroanilino)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound N=1C=NN2C=C(C(=O)OC)C=C2C=1NC1=CC=C(F)C(Cl)=C1 QRLJHZCWMRXNAP-UHFFFAOYSA-N 0.000 claims 1
- PTUUWGDLJHYULO-UHFFFAOYSA-N methyl 4-(3-cyano-4-methylanilino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC1=CC=C(C)C(C#N)=C1 PTUUWGDLJHYULO-UHFFFAOYSA-N 0.000 claims 1
- QNYCTGJEBPXCTG-UHFFFAOYSA-N methyl 4-(3-hydroxy-2-methylanilino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC1=CC=CC(O)=C1C QNYCTGJEBPXCTG-UHFFFAOYSA-N 0.000 claims 1
- YFGKHNXPJPMCFJ-UHFFFAOYSA-N methyl 4-(3-hydroxy-4-methoxyanilino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC1=CC=C(OC)C(O)=C1 YFGKHNXPJPMCFJ-UHFFFAOYSA-N 0.000 claims 1
- DWVFNSMCXULVNR-UHFFFAOYSA-N methyl 4-(3-hydroxy-4-methylanilino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC1=CC=C(C)C(O)=C1 DWVFNSMCXULVNR-UHFFFAOYSA-N 0.000 claims 1
- ZCTXKJKSADHBTO-UHFFFAOYSA-N methyl 4-(3-hydroxy-4-propylanilino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C1=C(O)C(CCC)=CC=C1NC1=NC=NN2C1=C(C)C(C(=O)OC)=C2 ZCTXKJKSADHBTO-UHFFFAOYSA-N 0.000 claims 1
- HDUYYHXMLYTCAI-UHFFFAOYSA-N methyl 4-(3-hydroxyanilino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC1=CC=CC(O)=C1 HDUYYHXMLYTCAI-UHFFFAOYSA-N 0.000 claims 1
- HGLFWYTYWBQLDW-UHFFFAOYSA-N methyl 4-(3-hydroxyphenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1OC1=CC=CC(O)=C1 HGLFWYTYWBQLDW-UHFFFAOYSA-N 0.000 claims 1
- UUJOHQIBEVTNOG-UHFFFAOYSA-N methyl 4-(3-methoxy-4-methylanilino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC1=CC=C(C)C(OC)=C1 UUJOHQIBEVTNOG-UHFFFAOYSA-N 0.000 claims 1
- WTYMKSGNONMYRW-UHFFFAOYSA-N methyl 4-(4-bromo-2-fluoroanilino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC1=CC=C(Br)C=C1F WTYMKSGNONMYRW-UHFFFAOYSA-N 0.000 claims 1
- PCZMZPUXORFNIP-UHFFFAOYSA-N methyl 4-(4-bromo-3-hydroxyanilino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC1=CC=C(Br)C(O)=C1 PCZMZPUXORFNIP-UHFFFAOYSA-N 0.000 claims 1
- MNNKPBFQXFETNB-UHFFFAOYSA-N methyl 4-(4-bromo-3-methylanilino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC1=CC=C(Br)C(C)=C1 MNNKPBFQXFETNB-UHFFFAOYSA-N 0.000 claims 1
- QHTGLKFZLNWNJC-UHFFFAOYSA-N methyl 4-(4-butyl-3-hydroxyanilino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C1=C(O)C(CCCC)=CC=C1NC1=NC=NN2C1=C(C)C(C(=O)OC)=C2 QHTGLKFZLNWNJC-UHFFFAOYSA-N 0.000 claims 1
- MNXPSLVOIQHJAN-UHFFFAOYSA-N methyl 4-(4-chloro-3-nitroanilino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC1=CC=C(Cl)C([N+]([O-])=O)=C1 MNXPSLVOIQHJAN-UHFFFAOYSA-N 0.000 claims 1
- OGMXRFDQJBXQMX-UHFFFAOYSA-N methyl 4-(4-cyano-3-hydroxyanilino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC1=CC=C(C#N)C(O)=C1 OGMXRFDQJBXQMX-UHFFFAOYSA-N 0.000 claims 1
- GVERDVRZRGMLFU-UHFFFAOYSA-N methyl 4-(4-methoxyanilino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC1=CC=C(OC)C=C1 GVERDVRZRGMLFU-UHFFFAOYSA-N 0.000 claims 1
- FJRJHNCPMQHVRO-UHFFFAOYSA-N methyl 4-[(1-acetyl-2,3-dihydroindol-6-yl)amino]-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C1=C2CCN(C(C)=O)C2=CC(NC2=NC=NN3C=C(C(=C32)C)C(=O)OC)=C1 FJRJHNCPMQHVRO-UHFFFAOYSA-N 0.000 claims 1
- QBXSUGIMUCOYBG-UHFFFAOYSA-N methyl 4-[(1-benzylindazol-5-yl)amino]-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC(C=C1C=N2)=CC=C1N2CC1=CC=CC=C1 QBXSUGIMUCOYBG-UHFFFAOYSA-N 0.000 claims 1
- WFERCNIAFVRWIY-UHFFFAOYSA-N methyl 4-[(1-benzylindazol-5-yl)amino]pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound N=1C=NN2C=C(C(=O)OC)C=C2C=1NC(C=C1C=N2)=CC=C1N2CC1=CC=CC=C1 WFERCNIAFVRWIY-UHFFFAOYSA-N 0.000 claims 1
- INVMEKIXYDZXNQ-UHFFFAOYSA-N methyl 4-[(3-hydroxy-4-methylphenyl)methylamino]-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NCC1=CC=C(C)C(O)=C1 INVMEKIXYDZXNQ-UHFFFAOYSA-N 0.000 claims 1
- VDUJRYXQQGCALE-UHFFFAOYSA-N methyl 4-[(4-hydroxynaphthalen-2-yl)amino]-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C1=CC=CC2=CC(NC3=NC=NN4C=C(C(=C43)C)C(=O)OC)=CC(O)=C21 VDUJRYXQQGCALE-UHFFFAOYSA-N 0.000 claims 1
- DVQZXKDRIWJVMP-UHFFFAOYSA-N methyl 4-[(6-methoxypyridin-3-yl)amino]-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC1=CC=C(OC)N=C1 DVQZXKDRIWJVMP-UHFFFAOYSA-N 0.000 claims 1
- VRUJTYVCDDGRAT-UHFFFAOYSA-N methyl 4-[3-(butylsulfamoyl)anilino]-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound CCCCNS(=O)(=O)C1=CC=CC(NC=2C3=C(C)C(C(=O)OC)=CN3N=CN=2)=C1 VRUJTYVCDDGRAT-UHFFFAOYSA-N 0.000 claims 1
- GYHKNUWTEFVSCN-UHFFFAOYSA-N methyl 4-[3-(hydrazinecarbonyl)anilino]-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC1=CC=CC(C(=O)NN)=C1 GYHKNUWTEFVSCN-UHFFFAOYSA-N 0.000 claims 1
- FBQMXMWCIZVMNC-UHFFFAOYSA-N methyl 4-[3-(hydroxymethyl)anilino]-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC1=CC=CC(CO)=C1 FBQMXMWCIZVMNC-UHFFFAOYSA-N 0.000 claims 1
- RFKITCWUSFYHIA-UHFFFAOYSA-N methyl 4-[3-(methanesulfonamido)-4-methylanilino]-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC1=CC=C(C)C(NS(C)(=O)=O)=C1 RFKITCWUSFYHIA-UHFFFAOYSA-N 0.000 claims 1
- KYLFAIGRMTXKCK-UHFFFAOYSA-N methyl 4-[4-(benzenesulfonamido)-3-hydroxyanilino]-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC(C=C1O)=CC=C1NS(=O)(=O)C1=CC=CC=C1 KYLFAIGRMTXKCK-UHFFFAOYSA-N 0.000 claims 1
- AIMDSXKCSQCTRF-UHFFFAOYSA-N methyl 4-[5-(dimethylsulfamoyl)-2-oxo-1,3-dihydroindol-3-yl]-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound O=C1NC2=CC=C(S(=O)(=O)N(C)C)C=C2C1C1=NC=NN2C=C(C(=O)OC)C(C)=C21 AIMDSXKCSQCTRF-UHFFFAOYSA-N 0.000 claims 1
- ACBLGNYVHXMIRT-UHFFFAOYSA-N methyl 4-[5-(methanesulfonamido)-2-methylanilino]-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC1=CC(NS(C)(=O)=O)=CC=C1C ACBLGNYVHXMIRT-UHFFFAOYSA-N 0.000 claims 1
- GRYZPPAQXDGZTR-UHFFFAOYSA-N methyl 5,6-dimethoxy-4-(2-oxo-1,3-dihydroindol-3-yl)pyrrolo[2,1-f][1,2,4]triazine-7-carboxylate Chemical compound O=C1NC2=CC=CC=C2C1C1=NC=NN2C(C(=O)OC)=C(OC)C(OC)=C21 GRYZPPAQXDGZTR-UHFFFAOYSA-N 0.000 claims 1
- RQLQWLJKCZHOIM-UHFFFAOYSA-N methyl 5-ethyl-4-[(6-methoxypyridin-3-yl)amino]pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(CC)C(C(=O)OC)=CN2N=CN=C1NC1=CC=C(OC)N=C1 RQLQWLJKCZHOIM-UHFFFAOYSA-N 0.000 claims 1
- QYEALBQJKRHZQW-UHFFFAOYSA-N methyl 5-methyl-4-(1H-pyrazol-5-ylamino)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC=1C=CNN=1 QYEALBQJKRHZQW-UHFFFAOYSA-N 0.000 claims 1
- MJBVBHIMQBVWOJ-UHFFFAOYSA-N methyl 5-methyl-4-(2-oxo-1,3-dihydroindol-3-yl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound O=C1NC2=CC=CC=C2C1C1=NC=NN2C=C(C(=O)OC)C(C)=C21 MJBVBHIMQBVWOJ-UHFFFAOYSA-N 0.000 claims 1
- DJKXWQNKGUHXMA-UHFFFAOYSA-N methyl 5-methyl-4-(2-oxo-3H-benzimidazol-1-yl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=CC=CC=C2NC(=O)N1C1=NC=NN2C=C(C(=O)OC)C(C)=C21 DJKXWQNKGUHXMA-UHFFFAOYSA-N 0.000 claims 1
- FULKGEZKAZEMGJ-UHFFFAOYSA-N methyl 5-methyl-4-(2-sulfamoylanilino)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC1=CC=CC=C1S(N)(=O)=O FULKGEZKAZEMGJ-UHFFFAOYSA-N 0.000 claims 1
- CJPKZAUMMYLARG-UHFFFAOYSA-N methyl 5-methyl-4-(3-oxo-1H-indazol-2-yl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound N1C2=CC=CC=C2C(=O)N1C1=NC=NN2C=C(C(=O)OC)C(C)=C21 CJPKZAUMMYLARG-UHFFFAOYSA-N 0.000 claims 1
- WQQASJBTDWIWDV-UHFFFAOYSA-N methyl 5-methyl-4-(3-oxo-2H-indazol-1-yl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound N1C(=O)C2=CC=CC=C2N1C1=NC=NN2C=C(C(=O)OC)C(C)=C21 WQQASJBTDWIWDV-UHFFFAOYSA-N 0.000 claims 1
- OHBZGSVBLWSOOC-UHFFFAOYSA-N methyl 5-methyl-4-(3-sulfamoylanilino)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC1=CC=CC(S(N)(=O)=O)=C1 OHBZGSVBLWSOOC-UHFFFAOYSA-N 0.000 claims 1
- RRFQIXSTCQXRJH-UHFFFAOYSA-N methyl 5-methyl-4-(4-methyl-3-nitroanilino)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC1=CC=C(C)C([N+]([O-])=O)=C1 RRFQIXSTCQXRJH-UHFFFAOYSA-N 0.000 claims 1
- CMHKTCZJLHLZPT-UHFFFAOYSA-N methyl 5-methyl-4-(4-methyl-3-sulfamoylanilino)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC1=CC=C(C)C(S(N)(=O)=O)=C1 CMHKTCZJLHLZPT-UHFFFAOYSA-N 0.000 claims 1
- JOHFSMPXICYLLT-UHFFFAOYSA-N methyl 5-methyl-4-(4-phenoxyanilino)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC(C=C1)=CC=C1OC1=CC=CC=C1 JOHFSMPXICYLLT-UHFFFAOYSA-N 0.000 claims 1
- HBINEOLOJHIXFU-UHFFFAOYSA-N methyl 5-methyl-4-(5-morpholin-4-ylsulfonyl-2-oxo-1,3-dihydroindol-3-yl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1C(C1=C2)C(=O)NC1=CC=C2S(=O)(=O)N1CCOCC1 HBINEOLOJHIXFU-UHFFFAOYSA-N 0.000 claims 1
- LRFKLXQCKKTUKG-UHFFFAOYSA-N methyl 5-methyl-4-(quinolin-5-ylamino)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C1=CC=C2C(NC3=NC=NN4C=C(C(=C43)C)C(=O)OC)=CC=CC2=N1 LRFKLXQCKKTUKG-UHFFFAOYSA-N 0.000 claims 1
- CKYTZCXEVIEESK-UHFFFAOYSA-N methyl 5-methyl-4-[(4-methyl-2-oxo-1H-quinolin-7-yl)amino]pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound CC1=CC(=O)NC2=CC(NC3=NC=NN4C=C(C(=C43)C)C(=O)OC)=CC=C21 CKYTZCXEVIEESK-UHFFFAOYSA-N 0.000 claims 1
- HSGHODFJKOHCLO-UHFFFAOYSA-N methyl 5-methyl-4-[(5-methyl-1H-pyrazol-3-yl)amino]pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC=1C=C(C)NN=1 HSGHODFJKOHCLO-UHFFFAOYSA-N 0.000 claims 1
- UQWPABVGTSYMKX-UHFFFAOYSA-N methyl 5-methyl-4-[(5-methylpyridin-2-yl)amino]pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1NC1=CC=C(C)C=N1 UQWPABVGTSYMKX-UHFFFAOYSA-N 0.000 claims 1
- VOUNLYITVOORCX-UHFFFAOYSA-N methyl 5-methyl-4-[2-oxo-5-(2-pyrrolidin-1-ylethylsulfamoyl)-1,3-dihydroindol-3-yl]pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1C(C1=C2)C(=O)NC1=CC=C2S(=O)(=O)NCCN1CCCC1 VOUNLYITVOORCX-UHFFFAOYSA-N 0.000 claims 1
- OGRZUAZSYFSVDR-UHFFFAOYSA-N methyl 5-methyl-4-[5-(2-morpholin-4-ylethylsulfamoyl)-2-oxo-1,3-dihydroindol-3-yl]pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C12=C(C)C(C(=O)OC)=CN2N=CN=C1C(C1=C2)C(=O)NC1=CC=C2S(=O)(=O)NCCN1CCOCC1 OGRZUAZSYFSVDR-UHFFFAOYSA-N 0.000 claims 1
- BHTATNLRPITTOG-UHFFFAOYSA-N methyl 5-methyl-4-[5-(methylsulfamoyl)-2-oxo-1,3-dihydroindol-3-yl]pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate Chemical compound C1=NN2C=C(C(=O)OC)C(C)=C2C(C2C(=O)NC3=CC=C(C=C32)S(=O)(=O)NC)=N1 BHTATNLRPITTOG-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 229960002653 nilutamide Drugs 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 230000037361 pathway Effects 0.000 claims 1
- 230000035699 permeability Effects 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrugs Drugs 0.000 claims 1
- RLNCTIUJEJXMBZ-UHFFFAOYSA-N pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide Chemical compound C1=NC=NN2C=C(C(=O)N)C=C21 RLNCTIUJEJXMBZ-UHFFFAOYSA-N 0.000 claims 1
- 230000019491 signal transduction Effects 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 1
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 229930003347 taxol Natural products 0.000 claims 1
- 229960000303 topotecan Drugs 0.000 claims 1
- 229960005026 toremifene Drugs 0.000 claims 1
- LXZZYRPGZAFOLE-UHFFFAOYSA-L transplatin Chemical compound [H][N]([H])([H])[Pt](Cl)(Cl)[N]([H])([H])[H] LXZZYRPGZAFOLE-UHFFFAOYSA-L 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 230000002792 vascular Effects 0.000 claims 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 claims 1
Claims (18)
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AU (1) | AU770377B2 (en) |
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CA (1) | CA2373990C (en) |
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EG (1) | EG24027A (en) |
ES (2) | ES2328269T3 (en) |
HK (1) | HK1041599B (en) |
HU (1) | HUP0301005A3 (en) |
IL (2) | IL144977A0 (en) |
MX (1) | MXPA01011832A (en) |
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TW (1) | TWI238163B (en) |
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ES2328269T3 (en) * | 1999-05-21 | 2009-11-11 | Bristol-Myers Squibb Company | PIRROLOTRIAZINAS AS INHIBIRES OF KINASES. |
JP4623483B2 (en) * | 1999-08-23 | 2011-02-02 | 塩野義製薬株式会社 | Pyrrotriazine derivative having sPLA2 inhibitory action |
MXPA03000874A (en) * | 2000-08-09 | 2003-06-06 | Astrazeneca Ab | Chemical compounds. |
ES2334641T3 (en) | 2000-09-01 | 2010-03-15 | Novartis Vaccines And Diagnostics, Inc. | AZA HETEROCICLIC DERIVATIVES AND THERAPEUTIC USE. |
ES2302106T3 (en) | 2000-09-11 | 2008-07-01 | Novartis Vaccines And Diagnostics, Inc. | PROCEDURE FOR PREPARATION OF BENCIMIDAZOL-2-IL QUINOLINE DERIVATIVES. |
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DK0682027T3 (en) * | 1994-05-03 | 1998-05-04 | Ciba Geigy Ag | Pyrrolopyrimidine derivatives with antiproliferative action |
GB9604361D0 (en) * | 1996-02-29 | 1996-05-01 | Pharmacia Spa | 4-Substituted pyrrolopyrimidine compounds as tyrosine kinase inhibitors |
ES2328269T3 (en) * | 1999-05-21 | 2009-11-11 | Bristol-Myers Squibb Company | PIRROLOTRIAZINAS AS INHIBIRES OF KINASES. |
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