JPWO2019233457A5 - - Google Patents
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- JPWO2019233457A5 JPWO2019233457A5 JP2020568258A JP2020568258A JPWO2019233457A5 JP WO2019233457 A5 JPWO2019233457 A5 JP WO2019233457A5 JP 2020568258 A JP2020568258 A JP 2020568258A JP 2020568258 A JP2020568258 A JP 2020568258A JP WO2019233457 A5 JPWO2019233457 A5 JP WO2019233457A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxymethyl
- benzyl
- pyrazine
- fluoro
- chloro
- 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.)
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- -1 5-Chloro-2- (isopropylamino) pyridin-4-yl Chemical group 0.000 claims 126
- 125000000623 heterocyclic group Chemical group 0.000 claims 31
- 150000001875 compounds Chemical class 0.000 claims 28
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 17
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 16
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 14
- 229910052736 halogen Inorganic materials 0.000 claims 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 150000002367 halogens Chemical class 0.000 claims 12
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 11
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 11
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 7
- 125000006713 (C5-C10) cycloalkyl group Chemical group 0.000 claims 5
- 206010028980 Neoplasm Diseases 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 4
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 4
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 4
- 125000003277 amino group Chemical group 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 201000009030 Carcinoma Diseases 0.000 claims 3
- 102100024193 Mitogen-activated protein kinase 1 Human genes 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims 2
- YXKIXCPSKHVEJS-UHFFFAOYSA-N 8-[5-chloro-2-(propan-2-ylamino)pyridin-4-yl]-2-[[2-(hydroxymethyl)phenyl]methyl]spiro[3,5-dihydropyrrolo[1,2-a][1,4]diazepine-4,3'-azetidine]-1-one Chemical compound ClC=1C(=CC(=NC=1)NC(C)C)C=1C=C2N(CC3(CN(C2=O)CC2=C(C=CC=C2)CO)CNC3)C=1 YXKIXCPSKHVEJS-UHFFFAOYSA-N 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 108010007457 Extracellular Signal-Regulated MAP Kinases Proteins 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 2
- 239000000463 material Substances 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- FYGJEYKUZTXBHD-XMMPIXPASA-N (3R)-2-[[5-fluoro-2-(hydroxymethyl)phenyl]methyl]-3-(methoxymethyl)-7-[2-(oxan-4-ylamino)pyridin-4-yl]-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound FC=1C=CC(=C(CN2C(C=3N(C[C@@H]2COC)C=C(C=3)C2=CC(=NC=C2)NC2CCOCC2)=O)C=1)CO FYGJEYKUZTXBHD-XMMPIXPASA-N 0.000 claims 1
- KCEFBLYMOFFYQK-HXUWFJFHSA-N (3R)-2-[[5-fluoro-2-(hydroxymethyl)phenyl]methyl]-3-(methoxymethyl)-7-[2-(propan-2-ylamino)pyrimidin-4-yl]-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound FC=1C=CC(=C(CN2C(C=3N(C[C@@H]2COC)C=C(C=3)C2=NC(=NC=C2)NC(C)C)=O)C=1)CO KCEFBLYMOFFYQK-HXUWFJFHSA-N 0.000 claims 1
- SJILUKLBRRWIJH-LJQANCHMSA-N (3R)-2-[[5-fluoro-2-(hydroxymethyl)phenyl]methyl]-3-(methoxymethyl)-7-[2-[(2-methylpyrazol-3-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound FC=1C=CC(=C(CN2C(C=3N(C[C@@H]2COC)C=C(C=3)C2=NC(=NC=C2C(F)(F)F)NC2=CC=NN2C)=O)C=1)CO SJILUKLBRRWIJH-LJQANCHMSA-N 0.000 claims 1
- SWKNIAWICMQSQS-OAQYLSRUSA-N (3R)-2-[[5-fluoro-2-(hydroxymethyl)phenyl]methyl]-3-(methoxymethyl)-7-[5-methyl-2-(propan-2-ylamino)pyrimidin-4-yl]-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound CC1=CN=C(N=C1C2=CN3C[C@@H](N(C(=O)C3=C2)CC4=C(C=CC(=C4)F)CO)COC)NC(C)C SWKNIAWICMQSQS-OAQYLSRUSA-N 0.000 claims 1
- IYEJMASQKZQPQU-HXUWFJFHSA-N (3R)-2-[[5-fluoro-2-(hydroxymethyl)phenyl]methyl]-7-[2-(2-methoxyethylamino)pyrimidin-4-yl]-3-(methoxymethyl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound FC=1C=CC(=C(CN2C(C=3N(C[C@@H]2COC)C=C(C=3)C2=NC(=NC=C2)NCCOC)=O)C=1)CO IYEJMASQKZQPQU-HXUWFJFHSA-N 0.000 claims 1
- XVLDBVVMKMORJB-HXUWFJFHSA-N (3R)-2-[[5-fluoro-2-(hydroxymethyl)phenyl]methyl]-7-[5-fluoro-2-(propan-2-ylamino)pyridin-4-yl]-3-(methoxymethyl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound FC=1C=CC(=C(CN2C(C=3N(C[C@@H]2COC)C=C(C=3)C2=CC(=NC=C2F)NC(C)C)=O)C=1)CO XVLDBVVMKMORJB-HXUWFJFHSA-N 0.000 claims 1
- ZAWLDGJWSZLFSH-HXUWFJFHSA-N (3R)-7-[2-(tert-butylamino)-5-chloropyridin-4-yl]-2-[[5-fluoro-2-(hydroxymethyl)phenyl]methyl]-3-(methoxymethyl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound C(C)(C)(C)NC1=NC=C(C(=C1)C=1C=C2N(C[C@@H](N(C2=O)CC2=C(C=CC(=C2)F)CO)COC)C=1)Cl ZAWLDGJWSZLFSH-HXUWFJFHSA-N 0.000 claims 1
- YCAUFIYMHHFWGG-HXUWFJFHSA-N (3R)-7-[5-chloro-2-(6,7-dihydro-4H-pyrano[4,3-d][1,3]thiazol-2-ylamino)pyridin-4-yl]-2-[[5-fluoro-2-(hydroxymethyl)phenyl]methyl]-3-(methoxymethyl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound ClC=1C(=CC(=NC=1)NC=1SC2=C(N=1)CCOC2)C=1C=C2N(C[C@@H](N(C2=O)CC2=C(C=CC(=C2)F)CO)COC)C=1 YCAUFIYMHHFWGG-HXUWFJFHSA-N 0.000 claims 1
- IKWJITVBAJYHEW-OAQYLSRUSA-N (3R)-7-[5-chloro-2-(cyclobutylamino)pyridin-4-yl]-2-[[5-fluoro-2-(hydroxymethyl)phenyl]methyl]-3-(methoxymethyl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound ClC=1C(=CC(=NC=1)NC1CCC1)C=1C=C2N(C[C@@H](N(C2=O)CC2=C(C=CC(=C2)F)CO)COC)C=1 IKWJITVBAJYHEW-OAQYLSRUSA-N 0.000 claims 1
- RGFOOWPEWNYPBZ-HSZRJFAPSA-N (3R)-7-[5-chloro-2-(cyclohexylamino)pyridin-4-yl]-2-[[5-fluoro-2-(hydroxymethyl)phenyl]methyl]-3-(methoxymethyl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound ClC=1C(=CC(=NC=1)NC1CCCCC1)C=1C=C2N(C[C@@H](N(C2=O)CC2=C(C=CC(=C2)F)CO)COC)C=1 RGFOOWPEWNYPBZ-HSZRJFAPSA-N 0.000 claims 1
- FZGAVPAHNQGDCT-JOCHJYFZSA-N (3R)-7-[5-chloro-2-(cyclopentylamino)pyridin-4-yl]-2-[[5-fluoro-2-(hydroxymethyl)phenyl]methyl]-3-(methoxymethyl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound ClC=1C(=CC(=NC=1)NC1CCCC1)C=1C=C2N(C[C@@H](N(C2=O)CC2=C(C=CC(=C2)F)CO)COC)C=1 FZGAVPAHNQGDCT-JOCHJYFZSA-N 0.000 claims 1
- KJDANSHIIORTDQ-HXUWFJFHSA-N (3R)-7-[5-chloro-2-(cyclopropylamino)pyridin-4-yl]-2-[[5-fluoro-2-(hydroxymethyl)phenyl]methyl]-3-(methoxymethyl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound ClC=1C(=CC(=NC=1)NC1CC1)C=1C=C2N(C[C@@H](N(C2=O)CC2=C(C=CC(=C2)F)CO)COC)C=1 KJDANSHIIORTDQ-HXUWFJFHSA-N 0.000 claims 1
- VMEQMKKLHWYOPQ-GOSISDBHSA-N (3R)-7-[5-chloro-2-(ethylamino)pyrimidin-4-yl]-2-[[5-fluoro-2-(hydroxymethyl)phenyl]methyl]-3-(methoxymethyl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound ClC=1C(=NC(=NC=1)NCC)C=1C=C2N(C[C@@H](N(C2=O)CC2=C(C=CC(=C2)F)CO)COC)C=1 VMEQMKKLHWYOPQ-GOSISDBHSA-N 0.000 claims 1
- JIOJEFNDCGLQEY-LJQANCHMSA-N (3R)-7-[5-chloro-2-(propan-2-ylamino)pyridin-4-yl]-2-[[5-fluoro-2-(hydroxymethyl)phenyl]methyl]-3-(hydroxymethyl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound ClC=1C(=CC(=NC=1)NC(C)C)C=1C=C2N(C[C@@H](N(C2=O)CC2=C(C=CC(=C2)F)CO)CO)C=1 JIOJEFNDCGLQEY-LJQANCHMSA-N 0.000 claims 1
- PLAYZCWFHSPTTP-HXUWFJFHSA-N (3R)-7-[5-chloro-2-(propan-2-ylamino)pyridin-4-yl]-2-[[5-fluoro-2-(hydroxymethyl)phenyl]methyl]-3-(methoxymethyl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound ClC=1C(=CC(=NC=1)NC(C)C)C=1C=C2N(C[C@@H](N(C2=O)CC2=C(C=CC(=C2)F)CO)COC)C=1 PLAYZCWFHSPTTP-HXUWFJFHSA-N 0.000 claims 1
- FXEAGPGQXCEWPE-OAQYLSRUSA-N (3R)-7-[5-chloro-2-[(1,3-dimethylpyrazol-4-yl)amino]pyridin-4-yl]-2-[[5-fluoro-2-(hydroxymethyl)phenyl]methyl]-3-(methoxymethyl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound ClC=1C(=CC(=NC=1)NC=1C(=NN(C=1)C)C)C=1C=C2N(C[C@@H](N(C2=O)CC2=C(C=CC(=C2)F)CO)COC)C=1 FXEAGPGQXCEWPE-OAQYLSRUSA-N 0.000 claims 1
- IZQRRCFLSVZTSP-HSZRJFAPSA-N (3R)-7-[5-chloro-2-[(1-methylpiperidin-4-yl)amino]pyridin-4-yl]-2-[[5-fluoro-2-(hydroxymethyl)phenyl]methyl]-3-(methoxymethyl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound ClC=1C(=CC(=NC=1)NC1CCN(CC1)C)C=1C=C2N(C[C@@H](N(C2=O)CC2=C(C=CC(=C2)F)CO)COC)C=1 IZQRRCFLSVZTSP-HSZRJFAPSA-N 0.000 claims 1
- HVCNUSNKWWXILG-OAQYLSRUSA-N (3R)-7-[5-chloro-2-[(2,4-dimethylpyrazol-3-yl)amino]pyridin-4-yl]-2-[[5-fluoro-2-(hydroxymethyl)phenyl]methyl]-3-(methoxymethyl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound ClC=1C(=CC(=NC1)NC1=C(C=NN1C)C)C=1C=C2N(C[C@@H](N(C2=O)CC2=C(C=CC(=C2)F)CO)COC)C1 HVCNUSNKWWXILG-OAQYLSRUSA-N 0.000 claims 1
- NCDUEFINTCOUKL-OAQYLSRUSA-N (3R)-7-[5-chloro-2-[(2,5-dimethylpyrazol-3-yl)amino]pyridin-4-yl]-2-[[5-fluoro-2-(hydroxymethyl)phenyl]methyl]-3-(methoxymethyl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound ClC=1C(=CC(=NC=1)NC1=CC(=NN1C)C)C=1C=C2N(C[C@@H](N(C2=O)CC2=C(C=CC(=C2)F)CO)COC)C=1 NCDUEFINTCOUKL-OAQYLSRUSA-N 0.000 claims 1
- DBJCABXBSDNPGJ-NSQNTRMNSA-N (3R)-7-[5-chloro-2-[(4-methoxycyclohexyl)amino]pyridin-4-yl]-2-[[5-fluoro-2-(hydroxymethyl)phenyl]methyl]-3-(methoxymethyl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound ClC=1C(=CC(=NC=1)NC1CCC(CC1)OC)C=1C=C2N(C[C@@H](N(C2=O)CC2=C(C=CC(=C2)F)CO)COC)C=1 DBJCABXBSDNPGJ-NSQNTRMNSA-N 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical compound N1C=CC=NC=C1 POXWDTQUDZUOGP-UHFFFAOYSA-N 0.000 claims 1
- LVXOIHLJIDKFNH-UHFFFAOYSA-N 2-[5-chloro-2-(propan-2-ylamino)pyridin-4-yl]-5-[[4,5-difluoro-2-(hydroxymethyl)phenyl]methyl]-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound ClC=1C(=CC(=NC=1)NC(C)C)C=1SC=2C(N(C=CC=2N=1)CC1=C(C=C(C(=C1)F)F)CO)=O LVXOIHLJIDKFNH-UHFFFAOYSA-N 0.000 claims 1
- VMPUURDQFVMHFB-UHFFFAOYSA-N 2-[[4-chloro-2-(hydroxymethyl)phenyl]methyl]-7-[5-chloro-2-(propan-2-ylamino)pyridin-4-yl]-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound ClC1=CC(=C(CN2C(C=3N(CC2)C=C(C=3)C2=CC(=NC=C2Cl)NC(C)C)=O)C=C1)CO VMPUURDQFVMHFB-UHFFFAOYSA-N 0.000 claims 1
- XFAKFVFJGHHWCZ-UHFFFAOYSA-N 2-[[4-chloro-2-(hydroxymethyl)phenyl]methyl]-8-[5-chloro-2-(propan-2-ylamino)pyridin-4-yl]spiro[3,5-dihydropyrrolo[1,2-a][1,4]diazepine-4,1'-cyclopropane]-1-one Chemical compound ClC1=CC(=C(CN2C(C=3N(CC4(C2)CC4)C=C(C=3)C2=CC(=NC=C2Cl)NC(C)C)=O)C=C1)CO XFAKFVFJGHHWCZ-UHFFFAOYSA-N 0.000 claims 1
- QMCNGDBIWSONHD-UHFFFAOYSA-N 2-[[5-fluoro-2-(hydroxymethyl)phenyl]methyl]-3-(hydroxymethyl)-7-[5-methyl-2-(oxetan-3-ylamino)pyrimidin-4-yl]-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound FC=1C=CC(=C(CN2C(C=3N(CC2CO)C=C(C=3)C2=NC(=NC=C2C)NC2COC2)=O)C=1)CO QMCNGDBIWSONHD-UHFFFAOYSA-N 0.000 claims 1
- NOSGRWUEQLJFDJ-UHFFFAOYSA-N 2-[[5-fluoro-2-(hydroxymethyl)phenyl]methyl]-7-[2-(propan-2-ylamino)-5-(trifluoromethyl)pyridin-4-yl]-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound FC=1C=CC(=C(CN2C(C=3N(CC2)C=C(C=3)C2=CC(=NC=C2C(F)(F)F)NC(C)C)=O)C=1)CO NOSGRWUEQLJFDJ-UHFFFAOYSA-N 0.000 claims 1
- SNSCPZAXJSVQIK-UHFFFAOYSA-N 2-[[5-fluoro-2-(hydroxymethyl)phenyl]methyl]-7-[5-methyl-2-(2-methylanilino)pyrimidin-4-yl]-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound FC=1C=CC(=C(CN2C(C=3N(CC2)C=C(C=3)C2=NC(=NC=C2C)NC2=C(C=CC=C2)C)=O)C=1)CO SNSCPZAXJSVQIK-UHFFFAOYSA-N 0.000 claims 1
- HSADKOSAEFXODI-UHFFFAOYSA-N 2-[[5-fluoro-2-(hydroxymethyl)phenyl]methyl]-7-[5-methyl-2-(oxetan-3-ylamino)pyrimidin-4-yl]-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound FC=1C=CC(=C(CN2C(C=3N(CC2)C=C(C=3)C2=NC(=NC=C2C)NC2COC2)=O)C=1)CO HSADKOSAEFXODI-UHFFFAOYSA-N 0.000 claims 1
- FAZGNDAMFDOISY-UHFFFAOYSA-N 2-[[5-fluoro-2-(hydroxymethyl)phenyl]methyl]-7-[5-methyl-2-(oxolan-3-ylamino)pyrimidin-4-yl]-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound FC=1C=CC(=C(CN2C(C=3N(CC2)C=C(C=3)C2=NC(=NC=C2C)NC2COCC2)=O)C=1)CO FAZGNDAMFDOISY-UHFFFAOYSA-N 0.000 claims 1
- AZHQSONCJYESIO-UHFFFAOYSA-N 2-[[5-fluoro-2-(hydroxymethyl)phenyl]methyl]-7-[5-methyl-2-(propan-2-ylamino)pyrimidin-4-yl]-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound FC=1C=CC(=C(CN2C(C=3N(CC2)C=C(C=3)C2=NC(=NC=C2C)NC(C)C)=O)C=1)CO AZHQSONCJYESIO-UHFFFAOYSA-N 0.000 claims 1
- IZCOKKXKKAWFQI-UHFFFAOYSA-N 2-[[5-fluoro-2-(hydroxymethyl)phenyl]methyl]-7-[5-methyl-2-[(1-methylindazol-4-yl)amino]pyrimidin-4-yl]-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound FC=1C=CC(=C(CN2C(C=3N(CC2)C=C(C=3)C2=NC(=NC=C2C)NC2=C3C=NN(C3=CC=C2)C)=O)C=1)CO IZCOKKXKKAWFQI-UHFFFAOYSA-N 0.000 claims 1
- REFFHZXOUNUVRY-UHFFFAOYSA-N 2-[[5-fluoro-2-(hydroxymethyl)phenyl]methyl]-7-[5-methyl-2-[(1-methylindazol-5-yl)amino]pyrimidin-4-yl]-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound FC=1C=CC(=C(CN2C(C=3N(CC2)C=C(C=3)C2=NC(=NC=C2C)NC=2C=C3C=NN(C3=CC=2)C)=O)C=1)CO REFFHZXOUNUVRY-UHFFFAOYSA-N 0.000 claims 1
- FGGUYAMWARKDAO-UHFFFAOYSA-N 2-[[5-fluoro-2-(hydroxymethyl)phenyl]methyl]-7-[5-methyl-2-[(1-methylindazol-7-yl)amino]pyrimidin-4-yl]-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound FC=1C=CC(=C(CN2C(C=3N(CC2)C=C(C=3)C2=NC(=NC=C2C)NC=2C=CC=C3C=NN(C=23)C)=O)C=1)CO FGGUYAMWARKDAO-UHFFFAOYSA-N 0.000 claims 1
- QFFBJNTYHGFVOA-UHFFFAOYSA-N 2-[[5-fluoro-2-(hydroxymethyl)phenyl]methyl]-7-[5-methyl-2-[(2-methylpyrazol-3-yl)amino]pyridin-4-yl]-3,4-dihydropyrrolo[1,2-a]pyrazin-1-one Chemical compound FC=1C=CC(=C(CN2C(C=3N(CC2)C=C(C=3)C2=CC(=NC=C2C)NC2=CC=NN2C)=O)C=1)CO QFFBJNTYHGFVOA-UHFFFAOYSA-N 0.000 claims 1
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| CN117209485A (zh) * | 2023-08-31 | 2023-12-12 | 四川大学华西医院 | 一种具有抗肿瘤活性的嘧啶骨架类化合物及其制备方法和应用 |
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| WO2016205418A1 (en) | 2015-06-15 | 2016-12-22 | Asana Biosciences, Llc | Heterocyclic inhibitors of erk1 and erk2 and their use in the treatment of cancer |
| WO2017080980A1 (en) * | 2015-11-09 | 2017-05-18 | Astrazeneca Ab | Dihydropyrrolopyrazinone derivatives useful in the treatment of cancer |
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