JP2016516817A5 - - Google Patents
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- Publication number
- JP2016516817A5 JP2016516817A5 JP2016509054A JP2016509054A JP2016516817A5 JP 2016516817 A5 JP2016516817 A5 JP 2016516817A5 JP 2016509054 A JP2016509054 A JP 2016509054A JP 2016509054 A JP2016509054 A JP 2016509054A JP 2016516817 A5 JP2016516817 A5 JP 2016516817A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydropyrazino
- pyrazin
- methyl
- pyridin
- triazol
- 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 18
- 206010028980 Neoplasm Diseases 0.000 claims 8
- 201000011510 cancer Diseases 0.000 claims 8
- -1 5-Fluoro-2-methyl-4- (1H-1,2,4-triazol-3-yl) phenyl Chemical group 0.000 claims 7
- 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 claims 7
- 102000013530 TOR Serine-Threonine Kinases Human genes 0.000 claims 7
- 229940043355 kinase inhibitor Drugs 0.000 claims 6
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims 6
- 208000028564 B-cell non-Hodgkin lymphoma Diseases 0.000 claims 5
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims 5
- 206010025323 Lymphomas Diseases 0.000 claims 5
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims 5
- HUTNOYOBQPAKIA-UHFFFAOYSA-N 1h-pyrazin-2-one Chemical compound OC1=CN=CC=N1 HUTNOYOBQPAKIA-UHFFFAOYSA-N 0.000 claims 4
- 239000002955 immunomodulating agent Substances 0.000 claims 4
- 229940121354 immunomodulator Drugs 0.000 claims 4
- 230000002584 immunomodulator Effects 0.000 claims 4
- 208000003950 B-cell lymphoma Diseases 0.000 claims 3
- 208000025205 Mantle-Cell Lymphoma Diseases 0.000 claims 3
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 201000003444 follicular lymphoma Diseases 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims 2
- 208000011691 Burkitt lymphomas Diseases 0.000 claims 2
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 208000013210 hematogenous Diseases 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 2
- 229960004942 lenalidomide Drugs 0.000 claims 2
- GOTYRUGSSMKFNF-UHFFFAOYSA-N lenalidomide Chemical group C1C=2C(N)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O GOTYRUGSSMKFNF-UHFFFAOYSA-N 0.000 claims 2
- 210000003800 pharynx Anatomy 0.000 claims 2
- 229960000688 pomalidomide Drugs 0.000 claims 2
- UVSMNLNDYGZFPF-UHFFFAOYSA-N pomalidomide Chemical compound O=C1C=2C(N)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O UVSMNLNDYGZFPF-UHFFFAOYSA-N 0.000 claims 2
- ZRGPQVFLCQCXGM-CQSZACIVSA-N (2r)-6-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-2-methyl-4-[2-(oxan-4-yl)ethyl]-1,2-dihydropyrazino[2,3-b]pyrazin-3-one Chemical compound N([C@@H](C1=O)C)C2=NC=C(C=3C=NC(=CC=3)C(C)(C)O)N=C2N1CCC1CCOCC1 ZRGPQVFLCQCXGM-CQSZACIVSA-N 0.000 claims 1
- ZRGPQVFLCQCXGM-AWEZNQCLSA-N (2s)-6-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-2-methyl-4-[2-(oxan-4-yl)ethyl]-1,2-dihydropyrazino[2,3-b]pyrazin-3-one Chemical compound N([C@H](C1=O)C)C2=NC=C(C=3C=NC(=CC=3)C(C)(C)O)N=C2N1CCC1CCOCC1 ZRGPQVFLCQCXGM-AWEZNQCLSA-N 0.000 claims 1
- DZTGDFKHOGKAQD-UHFFFAOYSA-N 3-(1h-benzimidazol-4-yl)-5-[2-(oxan-4-yl)ethyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound O=C1CNC2=NC=C(C=3C=4N=CNC=4C=CC=3)N=C2N1CCC1CCOCC1 DZTGDFKHOGKAQD-UHFFFAOYSA-N 0.000 claims 1
- QGIFMOBTYJUZDF-UHFFFAOYSA-N 3-(1h-imidazo[4,5-b]pyridin-6-yl)-5-[2-(oxan-4-yl)ethyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound O=C1CNC2=NC=C(C=3C=C4NC=NC4=NC=3)N=C2N1CCC1CCOCC1 QGIFMOBTYJUZDF-UHFFFAOYSA-N 0.000 claims 1
- ZGSASUQYKCYWOH-UHFFFAOYSA-N 3-(1h-indazol-4-yl)-5-(2-methoxyethyl)-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CCOC)C(=O)CNC2=NC=C1C1=CC=CC2=C1C=NN2 ZGSASUQYKCYWOH-UHFFFAOYSA-N 0.000 claims 1
- KEHLMISTGOWRBK-UHFFFAOYSA-N 3-(1h-indazol-4-yl)-5-[2-(oxan-4-yl)ethyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound O=C1CNC2=NC=C(C=3C=4C=NNC=4C=CC=3)N=C2N1CCC1CCOCC1 KEHLMISTGOWRBK-UHFFFAOYSA-N 0.000 claims 1
- GFRLZMVZCPDWRI-UHFFFAOYSA-N 3-(1h-indazol-5-yl)-5-[2-(oxan-4-yl)ethyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound O=C1CNC2=NC=C(C=3C=C4C=NNC4=CC=3)N=C2N1CCC1CCOCC1 GFRLZMVZCPDWRI-UHFFFAOYSA-N 0.000 claims 1
- SKIWQHRZDIRSSR-UHFFFAOYSA-N 3-(1h-indazol-6-yl)-5-(2-methoxyethyl)-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=C2C=NNC2=CC(C2=CN=C3NCC(=O)N(C3=N2)CCOC)=C1 SKIWQHRZDIRSSR-UHFFFAOYSA-N 0.000 claims 1
- JSQUAMCOBUROON-UHFFFAOYSA-N 3-(1h-indazol-6-yl)-5-[2-(oxan-4-yl)ethyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound O=C1CNC2=NC=C(C=3C=C4NN=CC4=CC=3)N=C2N1CCC1CCOCC1 JSQUAMCOBUROON-UHFFFAOYSA-N 0.000 claims 1
- LGPLNSCXMJYALD-UHFFFAOYSA-N 3-(1h-indol-4-yl)-5-[2-(oxan-4-yl)ethyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound O=C1CNC2=NC=C(C=3C=4C=CNC=4C=CC=3)N=C2N1CCC1CCOCC1 LGPLNSCXMJYALD-UHFFFAOYSA-N 0.000 claims 1
- HODBKAKOJZVOEF-UHFFFAOYSA-N 3-(1h-indol-5-yl)-5-[2-(oxan-4-yl)ethyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound O=C1CNC2=NC=C(C=3C=C4C=CNC4=CC=3)N=C2N1CCC1CCOCC1 HODBKAKOJZVOEF-UHFFFAOYSA-N 0.000 claims 1
- PLAKARKZIOKICJ-UHFFFAOYSA-N 3-(1h-indol-6-yl)-5-[2-(oxan-4-yl)ethyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound O=C1CNC2=NC=C(C=3C=C4NC=CC4=CC=3)N=C2N1CCC1CCOCC1 PLAKARKZIOKICJ-UHFFFAOYSA-N 0.000 claims 1
- MQPPZKPGGLJZKL-UHFFFAOYSA-N 3-(2-amino-7-methyl-3h-benzimidazol-5-yl)-5-(oxan-4-ylmethyl)-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C=1C=2NC(N)=NC=2C(C)=CC=1C(N=C12)=CN=C1NCC(=O)N2CC1CCOCC1 MQPPZKPGGLJZKL-UHFFFAOYSA-N 0.000 claims 1
- DKWHGLUBDUEFJU-UHFFFAOYSA-N 3-(2-amino-7-methyl-3h-benzimidazol-5-yl)-5-[2-(oxan-4-yl)ethyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C=1C=2NC(N)=NC=2C(C)=CC=1C(N=C12)=CN=C1NCC(=O)N2CCC1CCOCC1 DKWHGLUBDUEFJU-UHFFFAOYSA-N 0.000 claims 1
- UJPSHKFRYPVGNA-UHFFFAOYSA-N 3-(2-aminopyridin-4-yl)-5-[2-(oxan-4-yl)ethyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=NC(N)=CC(C=2N=C3N(CCC4CCOCC4)C(=O)CNC3=NC=2)=C1 UJPSHKFRYPVGNA-UHFFFAOYSA-N 0.000 claims 1
- MHYJMKMYZAYBRD-UHFFFAOYSA-N 3-(2-aminopyrimidin-5-yl)-5-[2-(oxan-4-yl)ethyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=NC(N)=NC=C1C1=CN=C(NCC(=O)N2CCC3CCOCC3)C2=N1 MHYJMKMYZAYBRD-UHFFFAOYSA-N 0.000 claims 1
- XUUDRYNLHCRUEM-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-5-[(3-methoxyphenyl)methyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical group COC1=CC=CC(CN2C3=NC(=CN=C3NCC2=O)C=2C=CC(O)=CC=2)=C1 XUUDRYNLHCRUEM-UHFFFAOYSA-N 0.000 claims 1
- WMCKBCJWRQYWFS-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-5-[2-(oxan-4-yl)ethyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=NC(N)=CC=C1C1=CN=C(NCC(=O)N2CCC3CCOCC3)C2=N1 WMCKBCJWRQYWFS-UHFFFAOYSA-N 0.000 claims 1
- YIBNAOSYIXQTJW-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-5-[2-(oxan-4-yl)ethyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=NC(OC)=CC=C1C1=CN=C(NCC(=O)N2CCC3CCOCC3)C2=N1 YIBNAOSYIXQTJW-UHFFFAOYSA-N 0.000 claims 1
- PMDUGGRRKRONFN-UHFFFAOYSA-N 3-(7-methyl-2-oxo-1,3-dihydrobenzimidazol-5-yl)-5-(oxan-4-ylmethyl)-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C=1C=2NC(=O)NC=2C(C)=CC=1C(N=C12)=CN=C1NCC(=O)N2CC1CCOCC1 PMDUGGRRKRONFN-UHFFFAOYSA-N 0.000 claims 1
- WVSLRWFLPGLENR-UHFFFAOYSA-N 3-[2-methyl-4-(1h-1,2,4-triazol-5-yl)phenyl]-5-[2-(oxan-4-yl)ethyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound CC1=CC(C2=NNC=N2)=CC=C1C(N=C12)=CN=C1NCC(=O)N2CCC1CCOCC1 WVSLRWFLPGLENR-UHFFFAOYSA-N 0.000 claims 1
- HYNXATWPOPIBJD-UHFFFAOYSA-N 3-[2-methyl-4-(1h-1,2,4-triazol-5-yl)phenyl]-7,8-dihydro-5h-pyrazino[2,3-b]pyrazin-6-one Chemical compound C=1C=C(C=2N=C3NC(=O)CNC3=NC=2)C(C)=CC=1C1=NN=CN1 HYNXATWPOPIBJD-UHFFFAOYSA-N 0.000 claims 1
- SXJWIRIRCLXOIF-UHFFFAOYSA-N 3-[2-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-5-(2-morpholin-4-ylethyl)-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound CC1=NC(C=2NC=NN=2)=CC=C1C(N=C12)=CN=C1NCC(=O)N2CCN1CCOCC1 SXJWIRIRCLXOIF-UHFFFAOYSA-N 0.000 claims 1
- YXNXKPZWTPLWQK-UHFFFAOYSA-N 3-[2-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-5-(oxan-4-yl)-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound CC1=NC(C=2NC=NN=2)=CC=C1C(N=C12)=CN=C1NCC(=O)N2C1CCOCC1 YXNXKPZWTPLWQK-UHFFFAOYSA-N 0.000 claims 1
- GSZOKDIAJHWSJC-UHFFFAOYSA-N 3-[2-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-5-(oxan-4-ylmethyl)-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound CC1=NC(C=2NC=NN=2)=CC=C1C(N=C12)=CN=C1NCC(=O)N2CC1CCOCC1 GSZOKDIAJHWSJC-UHFFFAOYSA-N 0.000 claims 1
- VLSSMLSPCKXABU-UHFFFAOYSA-N 3-[2-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-5-[2-(oxan-4-yl)ethyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound CC1=NC(C=2NC=NN=2)=CC=C1C(N=C12)=CN=C1NCC(=O)N2CCC1CCOCC1 VLSSMLSPCKXABU-UHFFFAOYSA-N 0.000 claims 1
- PYBNTHVXUJFNOG-UHFFFAOYSA-N 3-[2-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-5-propan-2-yl-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(C(C)C)C(=O)CNC2=NC=C1C(C(=N1)C)=CC=C1C1=NN=CN1 PYBNTHVXUJFNOG-UHFFFAOYSA-N 0.000 claims 1
- IEICKBNZQSCLBX-UHFFFAOYSA-N 3-[3-fluoro-2-methyl-4-(1h-1,2,4-triazol-5-yl)phenyl]-5-(2-methoxyethyl)-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CCOC)C(=O)CNC2=NC=C1C(C(=C1F)C)=CC=C1C=1N=CNN=1 IEICKBNZQSCLBX-UHFFFAOYSA-N 0.000 claims 1
- BATASGNNQUEPGG-UHFFFAOYSA-N 3-[3-fluoro-2-methyl-4-(1h-1,2,4-triazol-5-yl)phenyl]-5-[2-(oxan-4-yl)ethyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound CC1=C(F)C(C2=NNC=N2)=CC=C1C(N=C12)=CN=C1NCC(=O)N2CCC1CCOCC1 BATASGNNQUEPGG-UHFFFAOYSA-N 0.000 claims 1
- IWVZQMZLHLNEHO-UHFFFAOYSA-N 3-[3-fluoro-4-(1h-1,2,4-triazol-5-yl)phenyl]-5-(2-methoxyethyl)-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CCOC)C(=O)CNC2=NC=C1C(C=C1F)=CC=C1C1=NN=CN1 IWVZQMZLHLNEHO-UHFFFAOYSA-N 0.000 claims 1
- GCVDTBDFHANTQU-UHFFFAOYSA-N 3-[3-fluoro-4-(1h-1,2,4-triazol-5-yl)phenyl]-5-[2-(oxan-4-yl)ethyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound FC1=CC(C=2N=C3N(CCC4CCOCC4)C(=O)CNC3=NC=2)=CC=C1C1=NN=CN1 GCVDTBDFHANTQU-UHFFFAOYSA-N 0.000 claims 1
- DZUZGHMCJFXRHJ-UHFFFAOYSA-N 3-[4-(2-hydroxypropan-2-yl)phenyl]-5-(2-methoxyethyl)-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CCOC)C(=O)CNC2=NC=C1C1=CC=C(C(C)(C)O)C=C1 DZUZGHMCJFXRHJ-UHFFFAOYSA-N 0.000 claims 1
- DHITXWXYWZPVSM-UHFFFAOYSA-N 3-[4-(2-hydroxypropan-2-yl)phenyl]-5-[2-(oxan-4-yl)ethyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=CC(C(C)(O)C)=CC=C1C1=CN=C(NCC(=O)N2CCC3CCOCC3)C2=N1 DHITXWXYWZPVSM-UHFFFAOYSA-N 0.000 claims 1
- ZAPSUJZEAZNSRD-UHFFFAOYSA-N 3-[4-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-5-[2-(oxan-4-yl)ethyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound CC1=CC(C2=NNC=N2)=NC=C1C(N=C12)=CN=C1NCC(=O)N2CCC1CCOCC1 ZAPSUJZEAZNSRD-UHFFFAOYSA-N 0.000 claims 1
- UGKQZBCVFBXDFV-UHFFFAOYSA-N 3-[4-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-5-propan-2-yl-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(C(C)C)C(=O)CNC2=NC=C1C(C(=C1)C)=CN=C1C=1N=CNN=1 UGKQZBCVFBXDFV-UHFFFAOYSA-N 0.000 claims 1
- WRHQICCPKGSXAD-UHFFFAOYSA-N 3-[5-fluoro-2-methyl-4-(1h-1,2,4-triazol-5-yl)phenyl]-5-(2-methoxyethyl)-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CCOC)C(=O)CNC2=NC=C1C(C(=C1)C)=CC(F)=C1C=1N=CNN=1 WRHQICCPKGSXAD-UHFFFAOYSA-N 0.000 claims 1
- JCOCCYPZCGPHBP-UHFFFAOYSA-N 3-[5-fluoro-2-methyl-4-(1h-1,2,4-triazol-5-yl)phenyl]-5-(oxan-4-yl)-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound FC=1C=C(C=2N=C3N(C4CCOCC4)C(=O)CNC3=NC=2)C(C)=CC=1C=1N=CNN=1 JCOCCYPZCGPHBP-UHFFFAOYSA-N 0.000 claims 1
- OUEFEFGOKIPWCD-UHFFFAOYSA-N 3-[5-fluoro-2-methyl-4-(1h-1,2,4-triazol-5-yl)phenyl]-5-[2-(oxan-4-yl)ethyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound FC=1C=C(C=2N=C3N(CCC4CCOCC4)C(=O)CNC3=NC=2)C(C)=CC=1C1=NN=CN1 OUEFEFGOKIPWCD-UHFFFAOYSA-N 0.000 claims 1
- YFZUHPBRXXHHHX-UHFFFAOYSA-N 3-[5-fluoro-2-methyl-4-(1h-1,2,4-triazol-5-yl)phenyl]-5-propan-2-yl-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(C(C)C)C(=O)CNC2=NC=C1C(C(=C1)C)=CC(F)=C1C=1N=CNN=1 YFZUHPBRXXHHHX-UHFFFAOYSA-N 0.000 claims 1
- XSQAJVDTZWOBMX-UHFFFAOYSA-N 3-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-5-(2-methoxyethyl)-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CCOC)C(=O)CNC2=NC=C1C1=CC=C(C(C)(C)O)N=C1 XSQAJVDTZWOBMX-UHFFFAOYSA-N 0.000 claims 1
- TUHIMPAVUZMPBC-UHFFFAOYSA-N 3-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-5-(2-morpholin-4-ylethyl)-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NCC(=O)N2CCN3CCOCC3)C2=N1 TUHIMPAVUZMPBC-UHFFFAOYSA-N 0.000 claims 1
- AEGKAZZRRWFIHV-UHFFFAOYSA-N 3-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-5-(3-methoxypropyl)-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CCCOC)C(=O)CNC2=NC=C1C1=CC=C(C(C)(C)O)N=C1 AEGKAZZRRWFIHV-UHFFFAOYSA-N 0.000 claims 1
- IHCVPLCAIWFKAI-UHFFFAOYSA-N 3-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-5-(oxan-4-yl)-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NCC(=O)N2C3CCOCC3)C2=N1 IHCVPLCAIWFKAI-UHFFFAOYSA-N 0.000 claims 1
- HDJQPSZZAWLLJX-UHFFFAOYSA-N 3-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-5-(oxan-4-ylmethyl)-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NCC(=O)N2CC3CCOCC3)C2=N1 HDJQPSZZAWLLJX-UHFFFAOYSA-N 0.000 claims 1
- IZSFXJSROVCKBE-ZIAGYGMSSA-N 3-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-5-[(1r,3r)-3-methoxycyclopentyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1[C@H](OC)CC[C@H]1N1C2=NC(C=3C=NC(=CC=3)C(C)(C)O)=CN=C2NCC1=O IZSFXJSROVCKBE-ZIAGYGMSSA-N 0.000 claims 1
- IZSFXJSROVCKBE-KGLIPLIRSA-N 3-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-5-[(1r,3s)-3-methoxycyclopentyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1[C@@H](OC)CC[C@H]1N1C2=NC(C=3C=NC(=CC=3)C(C)(C)O)=CN=C2NCC1=O IZSFXJSROVCKBE-KGLIPLIRSA-N 0.000 claims 1
- IZSFXJSROVCKBE-UONOGXRCSA-N 3-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-5-[(1s,3r)-3-methoxycyclopentyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1[C@H](OC)CC[C@@H]1N1C2=NC(C=3C=NC(=CC=3)C(C)(C)O)=CN=C2NCC1=O IZSFXJSROVCKBE-UONOGXRCSA-N 0.000 claims 1
- IZSFXJSROVCKBE-KBPBESRZSA-N 3-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-5-[(1s,3s)-3-methoxycyclopentyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C=NC(=CC=3)C(C)(C)O)=CN=C2NCC1=O IZSFXJSROVCKBE-KBPBESRZSA-N 0.000 claims 1
- SSVPJPIEWYQHJS-UHFFFAOYSA-N 3-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-5-[2-(oxan-4-yl)ethyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NCC(=O)N2CCC3CCOCC3)C2=N1 SSVPJPIEWYQHJS-UHFFFAOYSA-N 0.000 claims 1
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-
2014
- 2014-04-16 CN CN201480034166.3A patent/CN105358177B/zh active Active
- 2014-04-16 JP JP2016509054A patent/JP6389241B2/ja active Active
- 2014-04-16 BR BR112015026006-3A patent/BR112015026006B1/pt active IP Right Grant
- 2014-04-16 CA CA2908954A patent/CA2908954C/en active Active
- 2014-04-16 HK HK16109226.9A patent/HK1221148A1/zh unknown
- 2014-04-16 EP EP14725324.9A patent/EP2986318A1/en not_active Withdrawn
- 2014-04-16 KR KR1020157030055A patent/KR102223060B1/ko active Active
- 2014-04-16 NZ NZ629456A patent/NZ629456A/en unknown
- 2014-04-16 US US14/254,019 patent/US20140314752A1/en not_active Abandoned
- 2014-04-16 TW TW103113965A patent/TW201526897A/zh unknown
- 2014-04-16 KR KR1020217005634A patent/KR102382576B1/ko active Active
- 2014-04-16 AU AU2014254056A patent/AU2014254056B2/en active Active
- 2014-04-16 WO PCT/US2014/034312 patent/WO2014172429A1/en not_active Ceased
- 2014-04-16 MX MX2015014596A patent/MX373803B/es active IP Right Grant
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2015
- 2015-10-08 IL IL241964A patent/IL241964B/en active IP Right Grant
- 2015-10-15 ZA ZA2015/07735A patent/ZA201507735B/en unknown
- 2015-10-16 MX MX2020003174A patent/MX2020003174A/es unknown
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2019
- 2019-12-11 US US16/710,551 patent/US20200113896A1/en not_active Abandoned
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