JP2018504449A5 - - Google Patents
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- Publication number
- JP2018504449A5 JP2018504449A5 JP2017541860A JP2017541860A JP2018504449A5 JP 2018504449 A5 JP2018504449 A5 JP 2018504449A5 JP 2017541860 A JP2017541860 A JP 2017541860A JP 2017541860 A JP2017541860 A JP 2017541860A JP 2018504449 A5 JP2018504449 A5 JP 2018504449A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- fluoro
- bipyridin
- pyrimidin
- bipyridine
- 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
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- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 7
- -1 hydroxy, amino Chemical group 0.000 claims 6
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 3
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims 2
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims 2
- 208000014644 Brain disease Diseases 0.000 claims 2
- MRPWZEBLZITJRD-UHFFFAOYSA-N CN(CC1)CCC1C1=CC(C2=CC=CC(C(C=CN=C3N)=C3F)=N2)=NC(N)=N1 Chemical compound CN(CC1)CCC1C1=CC(C2=CC=CC(C(C=CN=C3N)=C3F)=N2)=NC(N)=N1 MRPWZEBLZITJRD-UHFFFAOYSA-N 0.000 claims 2
- 102000003903 Cyclin-dependent kinases Human genes 0.000 claims 2
- 108090000266 Cyclin-dependent kinases Proteins 0.000 claims 2
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims 2
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 2
- QXRDCVLYOCTQRA-UHFFFAOYSA-N NC1=NC=CC(=C1F)C1=NC(=CC=C1)C1=NC(=NC(=C1C)C1CCN(CC1)C(C)C)N Chemical compound NC1=NC=CC(=C1F)C1=NC(=CC=C1)C1=NC(=NC(=C1C)C1CCN(CC1)C(C)C)N QXRDCVLYOCTQRA-UHFFFAOYSA-N 0.000 claims 2
- HVKXBOWCLHMPRY-UHFFFAOYSA-N NC1=NC=CC(=C1F)C1=NC(=CC=C1)C1=NC(=NC(=C1C)C1CCN(CC1)C)N Chemical compound NC1=NC=CC(=C1F)C1=NC(=CC=C1)C1=NC(=NC(=C1C)C1CCN(CC1)C)N HVKXBOWCLHMPRY-UHFFFAOYSA-N 0.000 claims 2
- XOVJLFUZECUJFT-UHFFFAOYSA-N NC1=NC=CC(=C1F)C1=NC(=CC=C1)C1=NC(=NC(=C1C)C1CCN(CC1)CC)N Chemical compound NC1=NC=CC(=C1F)C1=NC(=CC=C1)C1=NC(=NC(=C1C)C1CCN(CC1)CC)N XOVJLFUZECUJFT-UHFFFAOYSA-N 0.000 claims 2
- IXTJGGRZWJFXNL-UHFFFAOYSA-N NC1=NC=CC(=C1F)C1=NC(=CC=C1)C1=NC(=NC(=C1C)C1CCN(CC1)CCC)N Chemical compound NC1=NC=CC(=C1F)C1=NC(=CC=C1)C1=NC(=NC(=C1C)C1CCN(CC1)CCC)N IXTJGGRZWJFXNL-UHFFFAOYSA-N 0.000 claims 2
- XREIJTDAGVIUTJ-UHFFFAOYSA-N NC1=NC=CC(=C1F)C1=NC(=CC=C1)C1=NC(=NC(=C1C)C1CN(CCC1)C(C)C)N Chemical compound NC1=NC=CC(=C1F)C1=NC(=CC=C1)C1=NC(=NC(=C1C)C1CN(CCC1)C(C)C)N XREIJTDAGVIUTJ-UHFFFAOYSA-N 0.000 claims 2
- LQAIGLHYAGUIEN-UHFFFAOYSA-N NC1=NC=CC(=C1F)C1=NC(=CC=C1)C1=NC(=NC(=C1C)C1CN(CCC1)CCC)N Chemical compound NC1=NC=CC(=C1F)C1=NC(=CC=C1)C1=NC(=NC(=C1C)C1CN(CCC1)CCC)N LQAIGLHYAGUIEN-UHFFFAOYSA-N 0.000 claims 2
- AMDCZTGQWVIMSH-UHFFFAOYSA-N NC1=NC=CC(=C1F)C1=NC(=CC=C1)N1C(N=C(C(=C1)C)C1CN(CCC1)C)N Chemical compound NC1=NC=CC(=C1F)C1=NC(=CC=C1)N1C(N=C(C(=C1)C)C1CN(CCC1)C)N AMDCZTGQWVIMSH-UHFFFAOYSA-N 0.000 claims 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims 2
- BPEGJWRSRHCHSN-UHFFFAOYSA-N Temozolomide Chemical compound O=C1N(C)N=NC2=C(C(N)=O)N=CN21 BPEGJWRSRHCHSN-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 230000003412 degenerative effect Effects 0.000 claims 2
- ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 claims 2
- ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 claims 2
- 229910052736 halogen Chemical group 0.000 claims 2
- 150000002367 halogens Chemical group 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 229960004964 temozolomide Drugs 0.000 claims 2
- WYDUSKDSKCASEF-LJQANCHMSA-N (1s)-1-cyclohexyl-1-phenyl-3-pyrrolidin-1-ylpropan-1-ol Chemical compound C([C@](O)(C1CCCCC1)C=1C=CC=CC=1)CN1CCCC1 WYDUSKDSKCASEF-LJQANCHMSA-N 0.000 claims 1
- MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 claims 1
- VFVAQKKPFOPZEA-UHFFFAOYSA-N 2,6-bis(2-aminopyrimidin-4-yl)pyridin-3-ol Chemical compound NC1=NC=CC(=N1)C1=NC(=CC=C1O)C1=NC(=NC=C1)N VFVAQKKPFOPZEA-UHFFFAOYSA-N 0.000 claims 1
- VBKVZSGLBSHDDY-UHFFFAOYSA-N 2-(2-amino-5,6-dimethylpyrimidin-4-yl)-6-(2-amino-3-fluoropyridin-4-yl)pyridin-3-ol Chemical compound NC1=NC=CC(=C1F)C1=NC(=C(C=C1)O)C1=NC(=NC(=C1C)C)N VBKVZSGLBSHDDY-UHFFFAOYSA-N 0.000 claims 1
- CDXHEZRZLZUFTF-UHFFFAOYSA-N 2-(2-amino-5-ethylpyrimidin-4-yl)-6-(2-amino-3-fluoropyridin-4-yl)pyridin-3-ol Chemical compound NC1=NC=CC(=C1F)C1=NC(=C(C=C1)O)C1=NC(=NC=C1CC)N CDXHEZRZLZUFTF-UHFFFAOYSA-N 0.000 claims 1
- ULKJKOOARLOSTC-UHFFFAOYSA-N 2-(2-amino-6-chloropyrimidin-4-yl)-6-pyridin-4-ylpyridin-3-ol Chemical compound NC1=NC(=CC(=N1)C1=C(C=CC(=N1)C1=CC=NC=C1)O)Cl ULKJKOOARLOSTC-UHFFFAOYSA-N 0.000 claims 1
- PXPDMILZOQXUSI-UHFFFAOYSA-N 2-(2-amino-6-methylpyrimidin-4-yl)-6-(2,3-difluoro-4-hydroxyphenyl)pyridin-3-ol Chemical compound NC1=NC(=CC(=N1)C1=NC(=CC=C1O)C1=C(C(=C(C=C1)O)F)F)C PXPDMILZOQXUSI-UHFFFAOYSA-N 0.000 claims 1
- CJUCXVYWERHIBR-UHFFFAOYSA-N 2-(2-amino-6-methylpyrimidin-4-yl)-6-(2-fluoro-4-hydroxyphenyl)pyridin-3-ol Chemical compound NC1=NC(=CC(=N1)C1=NC(=CC=C1O)C1=C(C=C(C=C1)O)F)C CJUCXVYWERHIBR-UHFFFAOYSA-N 0.000 claims 1
- IWPJRURSBORDGS-UHFFFAOYSA-N 2-(2-amino-6-methylpyrimidin-4-yl)-6-(3-aminophenyl)pyridin-3-ol Chemical compound NC1=NC(=CC(=N1)C1=NC(=CC=C1O)C1=CC(=CC=C1)N)C IWPJRURSBORDGS-UHFFFAOYSA-N 0.000 claims 1
- MWTAGVAWBLPBMP-UHFFFAOYSA-N 2-(2-amino-6-methylpyrimidin-4-yl)-6-(3-fluoropyridin-4-yl)pyridin-3-ol Chemical compound NC1=NC(=CC(=N1)C1=C(C=CC(=N1)C1=C(C=NC=C1)F)O)C MWTAGVAWBLPBMP-UHFFFAOYSA-N 0.000 claims 1
- BDSAWBGLYKUYDH-UHFFFAOYSA-N 2-(2-amino-6-methylpyrimidin-4-yl)-6-(4-hydroxyphenyl)pyridin-3-ol Chemical compound NC1=NC(=CC(=N1)C1=NC(=CC=C1O)C1=CC=C(C=C1)O)C BDSAWBGLYKUYDH-UHFFFAOYSA-N 0.000 claims 1
- QYVXMISLDOLJLZ-UHFFFAOYSA-N 2-(2-amino-6-methylpyrimidin-4-yl)-6-pyridin-4-ylpyridin-3-ol Chemical compound NC1=NC(=CC(=N1)C1=C(C=CC(=N1)C1=CC=NC=C1)O)C QYVXMISLDOLJLZ-UHFFFAOYSA-N 0.000 claims 1
- IUURGEAKIXULKZ-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-6-(2,3-difluoro-4-hydroxyphenyl)pyridin-3-ol Chemical compound NC1=NC=CC(=N1)C1=NC(=CC=C1O)C1=C(C(=C(C=C1)O)F)F IUURGEAKIXULKZ-UHFFFAOYSA-N 0.000 claims 1
- XVKXFIJMBDLXDL-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-6-(2-fluoro-4-hydroxyphenyl)pyridin-3-ol Chemical compound NC1=NC=CC(=N1)C1=NC(=CC=C1O)C1=C(C=C(C=C1)O)F XVKXFIJMBDLXDL-UHFFFAOYSA-N 0.000 claims 1
- ZGWYJFSRHJXDKB-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-6-(3-fluoro-4-hydroxyphenyl)pyridin-3-ol Chemical compound NC1=NC=CC(=N1)C1=NC(=CC=C1O)C1=CC(=C(C=C1)O)F ZGWYJFSRHJXDKB-UHFFFAOYSA-N 0.000 claims 1
- AHUDUDDFNZTMJJ-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-6-(3-fluoropyridin-4-yl)pyridin-3-ol Chemical compound NC1=NC=CC(=N1)C1=C(C=CC(=N1)C1=C(C=NC=C1)F)O AHUDUDDFNZTMJJ-UHFFFAOYSA-N 0.000 claims 1
- IXMABNBCBJZVRT-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-6-(3-hydroxyphenyl)pyridin-3-ol Chemical compound NC1=NC=CC(=N1)C1=NC(=CC=C1O)C1=CC(=CC=C1)O IXMABNBCBJZVRT-UHFFFAOYSA-N 0.000 claims 1
- CTTUZLCFYRLJOD-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-6-(4-hydroxyphenyl)pyridin-3-ol Chemical compound NC1=NC=CC(=N1)C1=NC(=CC=C1O)C1=CC=C(C=C1)O CTTUZLCFYRLJOD-UHFFFAOYSA-N 0.000 claims 1
- CNJSKIQGLFEHSM-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-6-pyridin-3-ylpyridin-3-ol Chemical compound NC1=NC=CC(=N1)C1=C(C=CC(=N1)C=1C=NC=CC=1)O CNJSKIQGLFEHSM-UHFFFAOYSA-N 0.000 claims 1
- BGGFKMXFAFRLKE-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-6-pyridin-4-ylpyridin-3-ol Chemical compound NC1=NC=CC(=N1)C1=C(C=CC(=N1)C1=CC=NC=C1)O BGGFKMXFAFRLKE-UHFFFAOYSA-N 0.000 claims 1
- KOCDBXMUNMZOFD-UHFFFAOYSA-N 2-[2-amino-6-(1-ethylpiperidin-3-yl)pyrimidin-4-yl]-6-(2-amino-3-fluoropyridin-4-yl)pyridin-3-ol Chemical compound NC1=NC=CC(=C1F)C1=NC(=C(C=C1)O)C1=NC(=NC(=C1)C1CN(CCC1)CC)N KOCDBXMUNMZOFD-UHFFFAOYSA-N 0.000 claims 1
- JVFWWWWRIZOYBC-UHFFFAOYSA-N 2-[2-amino-6-(1-ethylpiperidin-4-yl)pyrimidin-4-yl]-6-(2-amino-3-fluoropyridin-4-yl)pyridin-3-ol Chemical compound NC1=NC=CC(=C1F)C1=NC(=C(C=C1)O)C1=NC(=NC(=C1)C1CCN(CC1)CC)N JVFWWWWRIZOYBC-UHFFFAOYSA-N 0.000 claims 1
- KHITZQQFUDDYOY-UHFFFAOYSA-N 2-[2-amino-6-(dimethylamino)pyrimidin-4-yl]-6-(2-amino-3-fluoropyridin-4-yl)pyridin-3-ol Chemical compound NC1=NC=CC(=C1F)C1=NC(=C(C=C1)O)C1=NC(=NC(=C1)N(C)C)N KHITZQQFUDDYOY-UHFFFAOYSA-N 0.000 claims 1
- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 claims 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- FKVHEFZQWCSWPF-UHFFFAOYSA-N 6-(2-amino-3-fluoropyridin-4-yl)-2-(2-amino-5-methylpyrimidin-4-yl)pyridin-3-ol Chemical compound NC1=NC=CC(=C1F)C1=NC(=C(C=C1)O)C1=NC(=NC=C1C)N FKVHEFZQWCSWPF-UHFFFAOYSA-N 0.000 claims 1
- ZPIBLZXCXVBUFZ-UHFFFAOYSA-N 6-(2-amino-3-fluoropyridin-4-yl)-2-(2-amino-5-propylpyrimidin-4-yl)pyridin-3-ol Chemical compound NC1=NC=CC(=C1F)C1=NC(=C(C=C1)O)C1=NC(=NC=C1CCC)N ZPIBLZXCXVBUFZ-UHFFFAOYSA-N 0.000 claims 1
- UQHDKUFLWKTTDL-UHFFFAOYSA-N 6-(2-amino-3-fluoropyridin-4-yl)-2-(2-amino-6-methylpyrimidin-4-yl)pyridin-3-ol Chemical compound NC1=NC=CC(=C1F)C1=NC(=C(C=C1)O)C1=NC(=NC(=C1)C)N UQHDKUFLWKTTDL-UHFFFAOYSA-N 0.000 claims 1
- SFMPGAKXIHSIGO-UHFFFAOYSA-N 6-(2-amino-3-fluoropyridin-4-yl)-2-(2-amino-6-morpholin-4-ylpyrimidin-4-yl)pyridin-3-ol Chemical compound NC1=NC=CC(=C1F)C1=NC(=C(C=C1)O)C1=NC(=NC(=C1)N1CCOCC1)N SFMPGAKXIHSIGO-UHFFFAOYSA-N 0.000 claims 1
- ICLXIERULPGRLV-UHFFFAOYSA-N 6-(2-amino-3-fluoropyridin-4-yl)-2-(2-amino-6-piperidin-4-ylpyrimidin-4-yl)pyridin-3-ol Chemical compound NC1=NC=CC(=C1F)C1=NC(=C(C=C1)O)C1=NC(=NC(=C1)C1CCNCC1)N ICLXIERULPGRLV-UHFFFAOYSA-N 0.000 claims 1
- DJRWECZCVWWHFC-UHFFFAOYSA-N 6-(2-amino-3-fluoropyridin-4-yl)-2-(2-amino-6-propan-2-ylpyrimidin-4-yl)pyridin-3-ol Chemical compound NC1=NC=CC(=C1F)C1=NC(=C(C=C1)O)C1=NC(=NC(=C1)C(C)C)N DJRWECZCVWWHFC-UHFFFAOYSA-N 0.000 claims 1
- LWMNKYLPBXRTDQ-UHFFFAOYSA-N 6-(2-amino-3-fluoropyridin-4-yl)-2-[2-amino-6-(1-methylpiperidin-3-yl)pyrimidin-4-yl]pyridin-3-ol Chemical compound NC1=NC=CC(=C1F)C1=NC(=C(C=C1)O)C1=NC(=NC(=C1)C1CN(CCC1)C)N LWMNKYLPBXRTDQ-UHFFFAOYSA-N 0.000 claims 1
- AQTUVYRUTYHIJX-UHFFFAOYSA-N 6-(2-amino-3-fluoropyridin-4-yl)-2-[2-amino-6-(1-methylpiperidin-4-yl)pyrimidin-4-yl]pyridin-3-ol Chemical compound NC1=NC=CC(=C1F)C1=NC(=C(C=C1)O)C1=NC(=NC(=C1)C1CCN(CC1)C)N AQTUVYRUTYHIJX-UHFFFAOYSA-N 0.000 claims 1
- YVSZJKLHXVFEQB-UHFFFAOYSA-N 6-(2-amino-3-fluoropyridin-4-yl)-2-[2-amino-6-(1-propan-2-ylpiperidin-3-yl)pyrimidin-4-yl]pyridin-3-ol Chemical compound NC1=NC=CC(=C1F)C1=NC(=C(C=C1)O)C1=NC(=NC(=C1)C1CN(CCC1)C(C)C)N YVSZJKLHXVFEQB-UHFFFAOYSA-N 0.000 claims 1
- DFUJTWCORWDBOJ-UHFFFAOYSA-N 6-(2-amino-3-fluoropyridin-4-yl)-2-[2-amino-6-(1-propan-2-ylpiperidin-4-yl)pyrimidin-4-yl]pyridin-3-ol Chemical compound NC1=NC=CC(=C1F)C1=NC(=C(C=C1)O)C1=NC(=NC(=C1)C1CCN(CC1)C(C)C)N DFUJTWCORWDBOJ-UHFFFAOYSA-N 0.000 claims 1
- JYTCKBDBQPIRRN-UHFFFAOYSA-N 6-(2-amino-3-fluoropyridin-4-yl)-2-[2-amino-6-(1-propylpiperidin-3-yl)pyrimidin-4-yl]pyridin-3-ol Chemical compound NC1=NC=CC(=C1F)C1=NC(=C(C=C1)O)C1=NC(=NC(=C1)C1CN(CCC1)CCC)N JYTCKBDBQPIRRN-UHFFFAOYSA-N 0.000 claims 1
- XUJAXYRASNBVNZ-UHFFFAOYSA-N 6-(2-amino-3-fluoropyridin-4-yl)-2-[2-amino-6-(1-propylpiperidin-4-yl)pyrimidin-4-yl]pyridin-3-ol Chemical compound NC1=NC=CC(=C1F)C1=NC(=C(C=C1)O)C1=NC(=NC(=C1)C1CCN(CC1)CCC)N XUJAXYRASNBVNZ-UHFFFAOYSA-N 0.000 claims 1
- MNJURBQBWJJSAF-UHFFFAOYSA-N 6-(2-amino-3-fluoropyridin-4-yl)-2-[2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]pyridin-3-ol Chemical compound NC1=NC=CC(=C1F)C1=NC(=C(C=C1)O)C1=NC(=NC(=C1)N1CCN(CC1)C)N MNJURBQBWJJSAF-UHFFFAOYSA-N 0.000 claims 1
- YWMJCIOQXWGOKM-UHFFFAOYSA-N 6-(2-amino-3-fluoropyridin-4-yl)-2-[2-amino-6-(oxan-4-yl)pyrimidin-4-yl]pyridin-3-ol Chemical compound NC1=NC=CC(=C1F)C1=NC(=C(C=C1)O)C1=NC(=NC(=C1)C1CCOCC1)N YWMJCIOQXWGOKM-UHFFFAOYSA-N 0.000 claims 1
- SGGNFNDFFIZBJK-UHFFFAOYSA-N 6-(2-amino-3-hydroxypyridin-4-yl)-2-(2-aminopyrimidin-4-yl)pyridin-3-ol Chemical compound NC1=NC=CC(=C1O)C1=NC(=C(C=C1)O)C1=NC(=NC=C1)N SGGNFNDFFIZBJK-UHFFFAOYSA-N 0.000 claims 1
- IJDIWAFBPDXFMW-UHFFFAOYSA-N 6-(2-aminopyridin-4-yl)-2-(2-aminopyrimidin-4-yl)pyridin-3-ol Chemical compound NC1=NC=CC(=C1)C1=NC(=C(C=C1)O)C1=NC(=NC=C1)N IJDIWAFBPDXFMW-UHFFFAOYSA-N 0.000 claims 1
- JQZYCLXXQNKVFS-UHFFFAOYSA-N 6-(3-amino-2-fluorophenyl)-2-(2-aminopyrimidin-4-yl)pyridin-3-ol Chemical compound NC=1C(=C(C=CC=1)C1=CC=C(C(=N1)C1=NC(=NC=C1)N)O)F JQZYCLXXQNKVFS-UHFFFAOYSA-N 0.000 claims 1
- CNHZNVAIYWPGGP-UHFFFAOYSA-N 6-(3-aminophenyl)-2-(2-aminopyrimidin-4-yl)pyridin-3-ol Chemical compound NC=1C=C(C=CC=1)C1=CC=C(C(=N1)C1=NC(=NC=C1)N)O CNHZNVAIYWPGGP-UHFFFAOYSA-N 0.000 claims 1
- LBGNAGATQGHENE-UHFFFAOYSA-N 6-(3-fluoropyridin-4-yl)pyridin-3-ol Chemical compound FC=1C=NC=CC=1C1=NC=C(C=C1)O LBGNAGATQGHENE-UHFFFAOYSA-N 0.000 claims 1
- ICMIEIUORHDHSN-UHFFFAOYSA-N 6-(4-amino-2-fluorophenyl)-2-(2-aminopyrimidin-4-yl)pyridin-3-ol Chemical compound NC1=CC(=C(C=C1)C1=CC=C(C(=N1)C1=NC(=NC=C1)N)O)F ICMIEIUORHDHSN-UHFFFAOYSA-N 0.000 claims 1
- WYWHKKSPHMUBEB-UHFFFAOYSA-N 6-Mercaptoguanine Natural products N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
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| KR102443873B1 (ko) * | 2019-09-06 | 2022-09-19 | 비욘드바이오주식회사 | 피리미딘일 바이피리딘 화합물의 제조방법 및 그를 위한 중간체 |
| KR20210029693A (ko) | 2019-09-06 | 2021-03-16 | 비욘드바이오주식회사 | 2,6-비스-(2-아미노피리미딘-4-일)피리딘-3-올 2염산염 및 이를 포함하는 약제학적 조성물 |
| MX2022005991A (es) * | 2019-11-18 | 2022-06-17 | Chugai Pharmaceutical Co Ltd | Farmaco combinado. |
| CN111558044B (zh) * | 2020-06-01 | 2022-02-11 | 中山大学肿瘤防治中心（中山大学附属肿瘤医院、中山大学肿瘤研究所） | 一种包含舒尼替尼的药物组合物及其制剂和应用 |
| CN116082310B (zh) * | 2023-02-17 | 2024-08-20 | 厦门大学 | 联吡啶酰胺类衍生物及其制备和应用 |
| CN116751195B (zh) * | 2023-06-21 | 2025-03-07 | 杭州科兴生物化工有限公司 | 联吡啶类化合物、其可药用的盐以及制备方法和应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6440965B1 (en) | 1997-10-15 | 2002-08-27 | Krenitsky Pharmaceuticals, Inc. | Substituted pyrimidine derivatives, their preparation and their use in the treatment of neurodegenerative or neurological disorders of the central nervous system |
| GB0013655D0 (en) * | 2000-06-05 | 2000-07-26 | Prolifix Ltd | Therapeutic compounds |
| ES2320973T3 (es) * | 2000-06-12 | 2009-06-01 | EISAI R&D MANAGEMENT CO., LTD. | Compuestos de 1,2-dihidropiridina, procedimiento para su preparacion y uso de los mismos. |
| JP2004534779A (ja) * | 2001-05-30 | 2004-11-18 | エルジー ライフサイエンス リミテッド | 疾病治療用プロテインキナーゼ阻害剤 |
| GB0129260D0 (en) * | 2001-12-06 | 2002-01-23 | Eisai London Res Lab Ltd | Pharmaceutical compositions and their uses |
| MXPA05001804A (es) * | 2002-08-14 | 2005-05-27 | Vertex Pharma | Inhibidores de proteinas cinasas y usos de los mismos. |
| CN1742723A (zh) | 2004-09-02 | 2006-03-08 | 天津倍方科技发展有限公司 | 含有替莫唑胺－8－羧酸酯的药物组合物以及该类化合物用于制备抗肿瘤药物的用途 |
| WO2008106202A1 (en) * | 2007-02-27 | 2008-09-04 | Housey Gerard M | Theramutein modulators |
| WO2010018458A2 (en) * | 2008-08-12 | 2010-02-18 | Crystalgenomics, Inc. | Phenol derivatives and methods of use thereof |
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2016
- 2016-02-02 SG SG11201705952SA patent/SG11201705952SA/en unknown
- 2016-02-02 ES ES16746826T patent/ES2854707T3/es active Active
- 2016-02-02 BR BR112017016465-5A patent/BR112017016465B1/pt active IP Right Grant
- 2016-02-02 JP JP2017541860A patent/JP6615899B2/ja active Active
- 2016-02-02 EP EP16746826.3A patent/EP3255042B1/en active Active
- 2016-02-02 DK DK16746826.3T patent/DK3255042T3/da active
- 2016-02-02 KR KR1020160013029A patent/KR101783642B1/ko active Active
- 2016-02-02 US US15/546,714 patent/US10227328B2/en active Active
- 2016-02-02 RU RU2017130825A patent/RU2710743C2/ru active
- 2016-02-02 WO PCT/KR2016/001133 patent/WO2016126085A2/ko not_active Ceased
- 2016-02-02 AU AU2016216253A patent/AU2016216253B2/en active Active
- 2016-02-02 CA CA2974788A patent/CA2974788C/en active Active
- 2016-02-02 CN CN201680008749.8A patent/CN107250130B/zh active Active
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