JP2013518890A5 - - Google Patents

Info

Publication number

JP2013518890A5

JP2013518890A5 JP2012552068A JP2012552068A JP2013518890A5 JP 2013518890 A5 JP2013518890 A5 JP 2013518890A5 JP 2012552068 A JP2012552068 A JP 2012552068A JP 2012552068 A JP2012552068 A JP 2012552068A JP 2013518890 A5 JP2013518890 A5 JP 2013518890A5

Authority

JP

Japan

Prior art keywords

pyrazin

dihydropyrazino

pyridin

methyl

triazol

Prior art date

2011-02-03

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Granted

Links

• Espacenet
• Global Dossier
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• -1 2-methyl-6- (4H-1,2,4-triazol-3-yl) pyridin-3-yl Chemical group 0.000 claims description 104
• 229940043355 kinase inhibitor Drugs 0.000 claims description 39
• 239000003757 phosphotransferase inhibitor Substances 0.000 claims description 39
• 102000013530 TOR Serine-Threonine Kinases Human genes 0.000 claims description 38
• 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 claims description 38
• HUTNOYOBQPAKIA-UHFFFAOYSA-N 1h-pyrazin-2-one Chemical group OC1=CN=CC=N1 HUTNOYOBQPAKIA-UHFFFAOYSA-N 0.000 claims description 27
• 150000003839 salts Chemical class 0.000 claims description 17
• 239000012453 solvate Substances 0.000 claims description 17
• 239000003814 drug Substances 0.000 claims description 11
• 208000011580 syndromic disease Diseases 0.000 claims 23
• 101000783681 Homo sapiens 5'-AMP-activated protein kinase catalytic subunit alpha-2 Proteins 0.000 claims 21
• 206010008342 Cervix carcinoma Diseases 0.000 claims 19
• 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 19
• 201000010881 cervical cancer Diseases 0.000 claims 19
• 101710181599 Serine/threonine-protein kinase STK11 Proteins 0.000 claims 18
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 17
• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 17
• 102100036009 5'-AMP-activated protein kinase catalytic subunit alpha-2 Human genes 0.000 claims 14
• UFKLYTOEMRFKAD-SHTZXODSSA-N C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C=NC(=CC=3)C(C)(C)O)=CN=C2NCC1=O Chemical group C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C=NC(=CC=3)C(C)(C)O)=CN=C2NCC1=O UFKLYTOEMRFKAD-SHTZXODSSA-N 0.000 claims 13
• 206010028980 Neoplasm Diseases 0.000 claims 11
• 201000011510 cancer Diseases 0.000 claims 11
• 238000004519 manufacturing process Methods 0.000 claims 10
• 102100026715 Serine/threonine-protein kinase STK11 Human genes 0.000 claims 9
• 230000000694 effects Effects 0.000 claims 7
• 108090000623 proteins and genes Proteins 0.000 claims 7
• 102000004169 proteins and genes Human genes 0.000 claims 7
• 238000012216 screening Methods 0.000 claims 6
• 239000008194 pharmaceutical composition Substances 0.000 claims 4
• 201000009030 Carcinoma Diseases 0.000 claims 3
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims 2
• 239000003153 chemical reaction reagent Substances 0.000 claims 2
• 239000003795 chemical substances by application Substances 0.000 claims 2
• 230000004153 glucose metabolism Effects 0.000 claims 2
• 230000004190 glucose uptake Effects 0.000 claims 2
• 201000005202 lung cancer Diseases 0.000 claims 2
• 208000020816 lung neoplasm Diseases 0.000 claims 2
• 230000003938 response to stress Effects 0.000 claims 2
• 239000003085 diluting agent Substances 0.000 claims 1
• 239000003937 drug carrier Substances 0.000 claims 1
• 239000000546 pharmaceutical excipient Substances 0.000 claims 1
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 27
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
• LAQJGAKLLZAETL-UHFFFAOYSA-N 2h-pyrazin-3-one Chemical compound O=C1CN=CC=N1 LAQJGAKLLZAETL-UHFFFAOYSA-N 0.000 description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 5
• 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 5
• 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
• 239000000651 prodrug Substances 0.000 description 3
• 229940002612 prodrug Drugs 0.000 description 3
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
• NRRUPCJJALELBB-UHFFFAOYSA-N 3-(2-morpholin-4-yl-2-oxoethyl)-5-[4-(1h-1,2,4-triazol-5-yl)phenyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1COCCN1C(=O)CN(C(NC1=NC=2)=O)C1=NC=2C(C=C1)=CC=C1C1=NN=CN1 NRRUPCJJALELBB-UHFFFAOYSA-N 0.000 description 2
• FWVUGLOSPMVGRD-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NC(=O)N2CC3CCCCC3)C2=N1 FWVUGLOSPMVGRD-UHFFFAOYSA-N 0.000 description 2
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
• DAERFROLXKHWOB-UHFFFAOYSA-N 5-(2-aminopyrimidin-5-yl)-3-(cyclohexylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=NC(N)=NC=C1C1=CN=C(NC(=O)N2CC3CCCCC3)C2=N1 DAERFROLXKHWOB-UHFFFAOYSA-N 0.000 description 2
• FELWYCRJYMPKOR-UHFFFAOYSA-N 5-(3h-benzimidazol-5-yl)-3-[2-(oxan-4-yl)ethyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=C4N=CNC4=CC=3)N=C2N1CCC1CCOCC1 FELWYCRJYMPKOR-UHFFFAOYSA-N 0.000 description 2
• HVUORIHKFKVNQF-UHFFFAOYSA-N 5-[4-(5-methyl-1h-1,2,4-triazol-3-yl)phenyl]-3-[2-(oxan-4-yl)ethyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound N1C(C)=NC(C=2C=CC(=CC=2)C=2N=C3N(CCC4CCOCC4)C(=O)NC3=NC=2)=N1 HVUORIHKFKVNQF-UHFFFAOYSA-N 0.000 description 2
• JSVFMHAWBTVCIZ-UHFFFAOYSA-N 5-[4-[5-(aminomethyl)-1h-1,2,4-triazol-3-yl]phenyl]-3-[2-(oxan-4-yl)ethyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound N1C(CN)=NC(C=2C=CC(=CC=2)C=2N=C3N(CCC4CCOCC4)C(=O)NC3=NC=2)=N1 JSVFMHAWBTVCIZ-UHFFFAOYSA-N 0.000 description 2
• WVFYKPHMSAZPQO-UHFFFAOYSA-N 5-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-3-(oxan-4-ylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NC(=O)N2CC3CCOCC3)C2=N1 WVFYKPHMSAZPQO-UHFFFAOYSA-N 0.000 description 2
• ONDJQRZDLSDOJA-UHFFFAOYSA-N 5-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-3-[2-(oxan-4-yl)ethyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NC(=O)N2CCC3CCOCC3)C2=N1 ONDJQRZDLSDOJA-UHFFFAOYSA-N 0.000 description 2
• LWYDBGXNFDMNFN-XYPYZODXSA-N O=C1NC=2C(C(=O)N)=NC(C=3C=C(O)C=CC=3)=NC=2N1[C@H]1CC[C@H](O)CC1 Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=C(O)C=CC=3)=NC=2N1[C@H]1CC[C@H](O)CC1 LWYDBGXNFDMNFN-XYPYZODXSA-N 0.000 description 2
• SHLJSRZKHPHFBY-XYPYZODXSA-N O=C1NC=2C(C(=O)N)=NC(C=3C=NC=CC=3)=NC=2N1[C@H]1CC[C@H](O)CC1 Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=NC=CC=3)=NC=2N1[C@H]1CC[C@H](O)CC1 SHLJSRZKHPHFBY-XYPYZODXSA-N 0.000 description 2
• ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 description 2
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 2
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
• 210000003000 inclusion body Anatomy 0.000 description 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 description 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 description 1
• ONKMZNCONQBICO-AWEZNQCLSA-N (3s)-6-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-3-methyl-4-[2-(oxan-4-yl)ethyl]-1,3-dihydropyrazino[2,3-b]pyrazin-2-one Chemical compound N1([C@H](C(NC2=NC=C(N=C21)C=1C=NC(=CC=1)C(C)(C)O)=O)C)CCC1CCOCC1 ONKMZNCONQBICO-AWEZNQCLSA-N 0.000 description 1
• CEPWLUZYNCRCNS-UHFFFAOYSA-N 1-(1-phenylethyl)-6-quinolin-5-yl-3h-imidazo[4,5-b]pyridin-2-one Chemical compound C12=CC(C=3C4=CC=CN=C4C=CC=3)=CN=C2NC(=O)N1C(C)C1=CC=CC=C1 CEPWLUZYNCRCNS-UHFFFAOYSA-N 0.000 description 1
• CEPWLUZYNCRCNS-OAHLLOKOSA-N 1-[(1r)-1-phenylethyl]-6-quinolin-5-yl-3h-imidazo[4,5-b]pyridin-2-one Chemical compound C1([C@@H](C)N2C(NC3=NC=C(C=C32)C=2C3=CC=CN=C3C=CC=2)=O)=CC=CC=C1 CEPWLUZYNCRCNS-OAHLLOKOSA-N 0.000 description 1
• JUAFWVKWYASFPF-OAHLLOKOSA-N 1-[(1r)-1-phenylethyl]-6-quinolin-5-yl-3h-imidazo[4,5-c]pyridin-2-one Chemical compound C1([C@@H](C)N2C(NC3=CN=C(C=C32)C=2C3=CC=CN=C3C=CC=2)=O)=CC=CC=C1 JUAFWVKWYASFPF-OAHLLOKOSA-N 0.000 description 1
• JUAFWVKWYASFPF-HNNXBMFYSA-N 1-[(1s)-1-phenylethyl]-6-quinolin-5-yl-3h-imidazo[4,5-c]pyridin-2-one Chemical compound C1([C@H](C)N2C(NC3=CN=C(C=C32)C=2C3=CC=CN=C3C=CC=2)=O)=CC=CC=C1 JUAFWVKWYASFPF-HNNXBMFYSA-N 0.000 description 1
• YMZQKMJPDBPOCQ-UHFFFAOYSA-N 1-[2-(oxan-4-yl)ethyl]-6-[4-(1h-1,2,4-triazol-5-yl)phenyl]-3h-imidazo[4,5-b]pyridin-2-one Chemical compound O=C1NC2=NC=C(C=3C=CC(=CC=3)C3=NNC=N3)C=C2N1CCC1CCOCC1 YMZQKMJPDBPOCQ-UHFFFAOYSA-N 0.000 description 1
• JBDILTKRCGFYLW-OAHLLOKOSA-N 1-methyl-3-[(1r)-1-phenylethyl]-5-quinolin-5-ylimidazo[4,5-b]pyrazin-2-one Chemical compound C1([C@@H](C)N2C(N(C)C3=NC=C(N=C32)C=2C3=CC=CN=C3C=CC=2)=O)=CC=CC=C1 JBDILTKRCGFYLW-OAHLLOKOSA-N 0.000 description 1
• JBDILTKRCGFYLW-HNNXBMFYSA-N 1-methyl-3-[(1s)-1-phenylethyl]-5-quinolin-5-ylimidazo[4,5-b]pyrazin-2-one Chemical compound C1([C@H](C)N2C(N(C)C3=NC=C(N=C32)C=2C3=CC=CN=C3C=CC=2)=O)=CC=CC=C1 JBDILTKRCGFYLW-HNNXBMFYSA-N 0.000 description 1
• NGQIDWQPIXGRGH-UHFFFAOYSA-N 1h-pyrazin-2-one;dihydrochloride Chemical compound Cl.Cl.O=C1C=NC=CN1 NGQIDWQPIXGRGH-UHFFFAOYSA-N 0.000 description 1
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 1
• XPHACYRJTQQTDD-UHFFFAOYSA-N 2-(1-benzylpiperidin-4-yl)-9-(2-methoxyphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C3CCN(CC=4C=CC=CC=4)CC3)N=C21 XPHACYRJTQQTDD-UHFFFAOYSA-N 0.000 description 1
• HVTVWALTSMUFLO-UHFFFAOYSA-N 2-(1h-benzimidazol-4-yl)-9-(2-methoxyphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=4N=CNC=4C=CC=3)N=C21 HVTVWALTSMUFLO-UHFFFAOYSA-N 0.000 description 1
• JGVQLNHQPVSEMZ-UHFFFAOYSA-N 2-(1h-imidazo[4,5-b]pyridin-6-yl)-8-[2-(oxan-4-yl)ethyl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C12=NC(C=3C=C4NC=NC4=NC=3)=CN=C2NC(=O)CN1CCC1CCOCC1 JGVQLNHQPVSEMZ-UHFFFAOYSA-N 0.000 description 1
• MOHLKOBIHZUNKX-UHFFFAOYSA-N 2-(1h-imidazo[4,5-b]pyridin-6-yl)-8-oxo-9-(2-propan-2-ylphenyl)-7h-purine-6-carboxamide Chemical compound CC(C)C1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C4NC=NC4=NC=3)N=C21 MOHLKOBIHZUNKX-UHFFFAOYSA-N 0.000 description 1
• DSCRDWSEOUIYPX-UHFFFAOYSA-N 2-(1h-imidazo[4,5-b]pyridin-6-yl)-8-oxo-9-[2-(trifluoromethyl)phenyl]-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=C4NC=NC4=NC=3)=NC=2N1C1=CC=CC=C1C(F)(F)F DSCRDWSEOUIYPX-UHFFFAOYSA-N 0.000 description 1
• NZOGAZZMGKUWIK-UHFFFAOYSA-N 2-(1h-imidazo[4,5-b]pyridin-6-yl)-9-(2-methoxyphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C4NC=NC4=NC=3)N=C21 NZOGAZZMGKUWIK-UHFFFAOYSA-N 0.000 description 1
• DMGNAUXWHPUTBF-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-9-(2-methoxyphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=4C=NNC=4C=CC=3)N=C21 DMGNAUXWHPUTBF-UHFFFAOYSA-N 0.000 description 1
• ZWGFWBUSBXEMAU-UHFFFAOYSA-N 2-(1h-indazol-5-yl)-8-[2-(oxan-4-yl)ethyl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C12=NC(C=3C=C4C=NNC4=CC=3)=CN=C2NC(=O)CN1CCC1CCOCC1 ZWGFWBUSBXEMAU-UHFFFAOYSA-N 0.000 description 1
• GPRUOGSZNIVNIG-UHFFFAOYSA-N 2-(1h-indazol-6-yl)-8-[2-(oxan-4-yl)ethyl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C12=NC(C=3C=C4NN=CC4=CC=3)=CN=C2NC(=O)CN1CCC1CCOCC1 GPRUOGSZNIVNIG-UHFFFAOYSA-N 0.000 description 1
• RATVQEQIHJFCQV-UHFFFAOYSA-N 2-(1h-indol-4-yl)-9-(2-methoxyphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=4C=CNC=4C=CC=3)N=C21 RATVQEQIHJFCQV-UHFFFAOYSA-N 0.000 description 1
• FLGMERISMNGPIM-UHFFFAOYSA-N 2-(1h-indol-5-yl)-8-[2-(oxan-4-yl)ethyl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C12=NC(C=3C=C4C=CNC4=CC=3)=CN=C2NC(=O)CN1CCC1CCOCC1 FLGMERISMNGPIM-UHFFFAOYSA-N 0.000 description 1
• UENIQAATCHHLCZ-UHFFFAOYSA-N 2-(1h-indol-5-yl)-8-oxo-9-(2-propan-2-ylphenyl)-7h-purine-6-carboxamide Chemical compound CC(C)C1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C4C=CNC4=CC=3)N=C21 UENIQAATCHHLCZ-UHFFFAOYSA-N 0.000 description 1
• UCNUXNCLAQVMMR-UHFFFAOYSA-N 2-(1h-indol-6-yl)-8-[2-(oxan-4-yl)ethyl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C12=NC(C=3C=C4NC=CC4=CC=3)=CN=C2NC(=O)CN1CCC1CCOCC1 UCNUXNCLAQVMMR-UHFFFAOYSA-N 0.000 description 1
• FVSMXVFQKIUDHE-UHFFFAOYSA-N 2-(1h-indol-6-yl)-9-(2-methoxyphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C4NC=CC4=CC=3)N=C21 FVSMXVFQKIUDHE-UHFFFAOYSA-N 0.000 description 1
• OVPLJWRLASUHJY-UHFFFAOYSA-N 2-(2-amino-7-methyl-3h-benzimidazol-5-yl)-8-[[3-(trifluoromethyl)phenyl]methyl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C=1C=2N=C(N)NC=2C(C)=CC=1C(N=C12)=CN=C1NC(=O)CN2CC1=CC=CC(C(F)(F)F)=C1 OVPLJWRLASUHJY-UHFFFAOYSA-N 0.000 description 1
• JAFHXNUYZPIAGR-UHFFFAOYSA-N 2-(2-chloropyridin-3-yl)-8-oxo-9-phenyl-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C(=NC=CC=3)Cl)=NC=2N1C1=CC=CC=C1 JAFHXNUYZPIAGR-UHFFFAOYSA-N 0.000 description 1
• TXLODQIAISBTAV-UHFFFAOYSA-N 2-(2-hydroxyanilino)-9-(2-methoxyphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(NC=3C(=CC=CC=3)O)N=C21 TXLODQIAISBTAV-UHFFFAOYSA-N 0.000 description 1
• NJCMAUCBBZGMEM-UHFFFAOYSA-N 2-(2-hydroxyethylamino)-9-(2-methoxyphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(NCCO)N=C21 NJCMAUCBBZGMEM-UHFFFAOYSA-N 0.000 description 1
• SAPUJGILULUQBA-UHFFFAOYSA-N 2-(2-hydroxyphenyl)-9-(2-methoxyphenyl)purine-6-carboxamide Chemical compound COC1=CC=CC=C1N1C2=NC(C=3C(=CC=CC=3)O)=NC(C(N)=O)=C2N=C1 SAPUJGILULUQBA-UHFFFAOYSA-N 0.000 description 1
• RIABHLXVSQJTOF-UHFFFAOYSA-N 2-(2-methoxypyridin-3-yl)-8-oxo-9-phenyl-7h-purine-6-carboxamide Chemical compound COC1=NC=CC=C1C1=NC(C(N)=O)=C(NC(=O)N2C=3C=CC=CC=3)C2=N1 RIABHLXVSQJTOF-UHFFFAOYSA-N 0.000 description 1
• HHLBMTJZXCKTAO-UHFFFAOYSA-N 2-(3-aminophenyl)-9-(2-methoxyphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C(N)C=CC=3)N=C21 HHLBMTJZXCKTAO-UHFFFAOYSA-N 0.000 description 1
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• FMIYVWZLZNGVQL-UHFFFAOYSA-N chembl1945788 Chemical compound C=1N=C2NC(=O)N(CC(C)C)C2=NC=1C1=CC=C(O)C=C1 FMIYVWZLZNGVQL-UHFFFAOYSA-N 0.000 description 1
• WYZYMIDBGQLLNH-UHFFFAOYSA-N chembl1945789 Chemical compound C1=CC(O)=CC=C1C1=CN=C(NC(=O)N2CC3CCOCC3)C2=N1 WYZYMIDBGQLLNH-UHFFFAOYSA-N 0.000 description 1
• OHAICBOAUVKDLU-UHFFFAOYSA-N chembl1945790 Chemical compound C1CN(C)CCC1CN1C(=O)NC2=NC=C(C=3C=CC(O)=CC=3)N=C21 OHAICBOAUVKDLU-UHFFFAOYSA-N 0.000 description 1
• WZORNRLHVWJBIW-UHFFFAOYSA-N chembl1945791 Chemical compound C1=CC(O)=CC=C1C1=CN=C(NC(=O)N2C3CCCCC3)C2=N1 WZORNRLHVWJBIW-UHFFFAOYSA-N 0.000 description 1
• FZEOTRKKKZKSFM-UHFFFAOYSA-N chembl1945792 Chemical compound C1=CC(O)=CC=C1C1=CN=C(NC(=O)N2C3CCOCC3)C2=N1 FZEOTRKKKZKSFM-UHFFFAOYSA-N 0.000 description 1
• FQJZWXRBDFNVOX-UHFFFAOYSA-N methyl 4-[3-(cyclohexylmethyl)-2-oxo-1h-imidazo[4,5-b]pyrazin-5-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CN=C(NC(=O)N2CC3CCCCC3)C2=N1 FQJZWXRBDFNVOX-UHFFFAOYSA-N 0.000 description 1
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
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• VHCVFIPXRYKNHG-UHFFFAOYSA-N n-[3-[2-oxo-3-(1-phenylethyl)-1h-imidazo[4,5-b]pyrazin-5-yl]phenyl]methanesulfonamide Chemical compound C12=NC(C=3C=C(NS(C)(=O)=O)C=CC=3)=CN=C2NC(=O)N1C(C)C1=CC=CC=C1 VHCVFIPXRYKNHG-UHFFFAOYSA-N 0.000 description 1
• HDJQSVHBEAPTEU-UHFFFAOYSA-N n-[4-[2-oxo-3-(1-phenylethyl)-1h-imidazo[4,5-b]pyrazin-5-yl]phenyl]methanesulfonamide Chemical compound C12=NC(C=3C=CC(NS(C)(=O)=O)=CC=3)=CN=C2NC(=O)N1C(C)C1=CC=CC=C1 HDJQSVHBEAPTEU-UHFFFAOYSA-N 0.000 description 1
• KLWFNAQFZRJTAU-UHFFFAOYSA-N n-[5-[2-(oxan-4-yl)ethyl]-6-oxo-7,8-dihydropyrazino[2,3-b]pyrazin-3-yl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(N=C12)=CN=C1NCC(=O)N2CCC1CCOCC1 KLWFNAQFZRJTAU-UHFFFAOYSA-N 0.000 description 1
• MBAYAFKPPQIRLP-UHFFFAOYSA-N n-methyl-4-[3-(oxan-4-ylmethyl)-2-oxo-1h-imidazo[4,5-b]pyrazin-5-yl]benzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=CN=C(NC(=O)N2CC3CCOCC3)C2=N1 MBAYAFKPPQIRLP-UHFFFAOYSA-N 0.000 description 1
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• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
• IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 1
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1