KR20200034818A - Tor 키나제 억제제를 사용한 암의 치료 - Google Patents
Tor 키나제 억제제를 사용한 암의 치료 Download PDFInfo
- Publication number
- KR20200034818A KR20200034818A KR1020207008188A KR20207008188A KR20200034818A KR 20200034818 A KR20200034818 A KR 20200034818A KR 1020207008188 A KR1020207008188 A KR 1020207008188A KR 20207008188 A KR20207008188 A KR 20207008188A KR 20200034818 A KR20200034818 A KR 20200034818A
- Authority
- KR
- South Korea
- Prior art keywords
- substituted
- unsubstituted
- pyrazin
- tor kinase
- methyl
- 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.)
- Ceased
Links
- 206010028980 Neoplasm Diseases 0.000 title claims description 81
- 238000011282 treatment Methods 0.000 title claims description 36
- 229940043355 kinase inhibitor Drugs 0.000 title abstract description 356
- 239000003757 phosphotransferase inhibitor Substances 0.000 title abstract description 356
- 201000011510 cancer Diseases 0.000 title description 13
- 102000013530 TOR Serine-Threonine Kinases Human genes 0.000 claims abstract description 374
- 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 claims abstract description 374
- 208000006168 Ewing Sarcoma Diseases 0.000 claims abstract description 75
- 238000000034 method Methods 0.000 claims abstract description 31
- -1 6- (2-hydroxypropan-2-yl) pyridin-3-yl Chemical group 0.000 claims description 199
- HUTNOYOBQPAKIA-UHFFFAOYSA-N 1h-pyrazin-2-one Chemical compound OC1=CN=CC=N1 HUTNOYOBQPAKIA-UHFFFAOYSA-N 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 33
- 230000037361 pathway Effects 0.000 claims description 15
- 230000004044 response Effects 0.000 claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 108091007960 PI3Ks Proteins 0.000 claims description 10
- 230000002018 overexpression Effects 0.000 claims description 7
- 239000002552 dosage form Substances 0.000 claims description 5
- 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 claims description 4
- 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 claims description 4
- 238000011156 evaluation Methods 0.000 claims description 4
- 230000035772 mutation Effects 0.000 claims description 4
- YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 claims description 4
- 102000014160 PTEN Phosphohydrolase Human genes 0.000 claims description 3
- 108010011536 PTEN Phosphohydrolase Proteins 0.000 claims description 3
- 102000010400 1-phosphatidylinositol-3-kinase activity proteins Human genes 0.000 claims 4
- UFKLYTOEMRFKAD-UHFFFAOYSA-N 3-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-5-(4-methoxycyclohexyl)-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1CC(OC)CCC1N1C2=NC(C=3C=NC(=CC=3)C(C)(C)O)=CN=C2NCC1=O UFKLYTOEMRFKAD-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 description 214
- 125000003118 aryl group Chemical group 0.000 description 129
- 150000001875 compounds Chemical class 0.000 description 113
- 125000000753 cycloalkyl group Chemical group 0.000 description 96
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 78
- 125000001072 heteroaryl group Chemical group 0.000 description 77
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 77
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 42
- 229940125904 compound 1 Drugs 0.000 description 36
- 125000000623 heterocyclic group Chemical group 0.000 description 33
- 239000000203 mixture Substances 0.000 description 33
- 125000001424 substituent group Chemical group 0.000 description 32
- 108010006124 DNA-Activated Protein Kinase Proteins 0.000 description 31
- 102000005768 DNA-Activated Protein Kinase Human genes 0.000 description 31
- 210000004027 cell Anatomy 0.000 description 29
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 24
- 239000003814 drug Substances 0.000 description 24
- 230000005764 inhibitory process Effects 0.000 description 23
- 239000000651 prodrug Substances 0.000 description 23
- 229940002612 prodrug Drugs 0.000 description 23
- 125000003107 substituted aryl group Chemical group 0.000 description 23
- 125000003545 alkoxy group Chemical group 0.000 description 22
- 229940079593 drug Drugs 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 22
- 125000004093 cyano group Chemical group *C#N 0.000 description 21
- 239000012453 solvate Substances 0.000 description 20
- 230000000694 effects Effects 0.000 description 19
- 229910052736 halogen Inorganic materials 0.000 description 18
- 150000002367 halogens Chemical class 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 18
- 150000003222 pyridines Chemical class 0.000 description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 17
- 238000004458 analytical method Methods 0.000 description 16
- 201000010099 disease Diseases 0.000 description 16
- 229910052760 oxygen Inorganic materials 0.000 description 15
- 125000004076 pyridyl group Chemical group 0.000 description 15
- 102000001253 Protein Kinase Human genes 0.000 description 14
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 14
- 229910052739 hydrogen Inorganic materials 0.000 description 14
- 108060006633 protein kinase Proteins 0.000 description 14
- 150000003248 quinolines Chemical class 0.000 description 14
- 208000011581 secondary neoplasm Diseases 0.000 description 14
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 13
- 125000003342 alkenyl group Chemical group 0.000 description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- 125000001624 naphthyl group Chemical group 0.000 description 13
- 208000024891 symptom Diseases 0.000 description 13
- 125000004429 atom Chemical group 0.000 description 12
- 238000001574 biopsy Methods 0.000 description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 12
- 102100022466 Eukaryotic translation initiation factor 4E-binding protein 1 Human genes 0.000 description 11
- 108050000946 Eukaryotic translation initiation factor 4E-binding protein 1 Proteins 0.000 description 11
- 239000002775 capsule Substances 0.000 description 11
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 11
- 239000000523 sample Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000003826 tablet Substances 0.000 description 11
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 10
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 125000003226 pyrazolyl group Chemical group 0.000 description 10
- 150000003254 radicals Chemical group 0.000 description 10
- 230000009467 reduction Effects 0.000 description 10
- 108091000080 Phosphotransferase Proteins 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 9
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 9
- 238000001802 infusion Methods 0.000 description 9
- 230000002401 inhibitory effect Effects 0.000 description 9
- 102000020233 phosphotransferase Human genes 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 8
- 239000012472 biological sample Substances 0.000 description 8
- 230000037396 body weight Effects 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 238000011161 development Methods 0.000 description 8
- 230000018109 developmental process Effects 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- 108090000623 proteins and genes Proteins 0.000 description 8
- 150000003230 pyrimidines Chemical class 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- 229930192474 thiophene Natural products 0.000 description 8
- 150000003577 thiophenes Chemical class 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 229920002472 Starch Polymers 0.000 description 7
- 125000003710 aryl alkyl group Chemical group 0.000 description 7
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 7
- 230000003111 delayed effect Effects 0.000 description 7
- 231100000371 dose-limiting toxicity Toxicity 0.000 description 7
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 7
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 7
- 230000026731 phosphorylation Effects 0.000 description 7
- 238000006366 phosphorylation reaction Methods 0.000 description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 239000008107 starch Substances 0.000 description 7
- 235000019698 starch Nutrition 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 125000001425 triazolyl group Chemical group 0.000 description 7
- 230000004614 tumor growth Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 6
- VTSCFUAJBOFZEI-UHFFFAOYSA-N 8-oxo-9-phenyl-2-pyridin-3-yl-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=NC=CC=3)=NC=2N1C1=CC=CC=C1 VTSCFUAJBOFZEI-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 102000038030 PI3Ks Human genes 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 6
- 150000002475 indoles Chemical class 0.000 description 6
- 125000001041 indolyl group Chemical group 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 230000036961 partial effect Effects 0.000 description 6
- 230000002265 prevention Effects 0.000 description 6
- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical class C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 6
- 230000004083 survival effect Effects 0.000 description 6
- 239000003981 vehicle Substances 0.000 description 6
- 0 *c(nc1N2C3C(C*=C)CC2)cnc1NC3=O Chemical compound *c(nc1N2C3C(C*=C)CC2)cnc1NC3=O 0.000 description 5
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 230000005778 DNA damage Effects 0.000 description 5
- 231100000277 DNA damage Toxicity 0.000 description 5
- 108010035196 Mechanistic Target of Rapamycin Complex 1 Proteins 0.000 description 5
- 102000008135 Mechanistic Target of Rapamycin Complex 1 Human genes 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 239000001913 cellulose Substances 0.000 description 5
- 206010012601 diabetes mellitus Diseases 0.000 description 5
- 125000001188 haloalkyl group Chemical group 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 230000000155 isotopic effect Effects 0.000 description 5
- 230000027405 negative regulation of phosphorylation Effects 0.000 description 5
- 150000003053 piperidines Chemical class 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
- 125000006413 ring segment Chemical group 0.000 description 5
- 235000000346 sugar Nutrition 0.000 description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 4
- QEVNUSASORPKFA-UHFFFAOYSA-N 9-benzyl-2-methylpurine-6-carboxamide Chemical compound C12=NC(C)=NC(C(N)=O)=C2N=CN1CC1=CC=CC=C1 QEVNUSASORPKFA-UHFFFAOYSA-N 0.000 description 4
- OCXWDXMLAQPCKK-UHFFFAOYSA-N 9-benzylpurine-2,6-dicarboxamide Chemical compound C12=NC(C(=O)N)=NC(C(N)=O)=C2N=CN1CC1=CC=CC=C1 OCXWDXMLAQPCKK-UHFFFAOYSA-N 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- 229920000936 Agarose Polymers 0.000 description 4
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 4
- 206010061818 Disease progression Diseases 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- 229930195725 Mannitol Natural products 0.000 description 4
- 108010034057 Mechanistic Target of Rapamycin Complex 2 Proteins 0.000 description 4
- 102000009308 Mechanistic Target of Rapamycin Complex 2 Human genes 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 102100023421 Nuclear receptor ROR-gamma Human genes 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 235000010443 alginic acid Nutrition 0.000 description 4
- 229920000615 alginic acid Polymers 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 239000000090 biomarker Substances 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 235000010980 cellulose Nutrition 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 230000005750 disease progression Effects 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 108020001507 fusion proteins Proteins 0.000 description 4
- 102000037865 fusion proteins Human genes 0.000 description 4
- 125000002883 imidazolyl group Chemical group 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- 239000000594 mannitol Substances 0.000 description 4
- 235000010355 mannitol Nutrition 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 229920000609 methyl cellulose Polymers 0.000 description 4
- 239000001923 methylcellulose Substances 0.000 description 4
- 235000010981 methylcellulose Nutrition 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 231100000252 nontoxic Toxicity 0.000 description 4
- 230000003000 nontoxic effect Effects 0.000 description 4
- 125000005936 piperidyl group Chemical group 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 125000000168 pyrrolyl group Chemical group 0.000 description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 4
- 238000001959 radiotherapy Methods 0.000 description 4
- ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 4
- 230000009291 secondary effect Effects 0.000 description 4
- 210000002966 serum Anatomy 0.000 description 4
- 229960002930 sirolimus Drugs 0.000 description 4
- 238000011255 standard chemotherapy Methods 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 238000001356 surgical procedure Methods 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- 210000004881 tumor cell Anatomy 0.000 description 4
- LAQJGAKLLZAETL-UHFFFAOYSA-N 2h-pyrazin-3-one Chemical compound O=C1CN=CC=N1 LAQJGAKLLZAETL-UHFFFAOYSA-N 0.000 description 3
- GCXKRALLDQJMGT-UHFFFAOYSA-N 5-[3-methyl-4-(1h-1,2,4-triazol-5-yl)phenyl]-3-(oxan-4-ylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound CC1=CC(C=2N=C3N(CC4CCOCC4)C(=O)NC3=NC=2)=CC=C1C=1N=CNN=1 GCXKRALLDQJMGT-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- 206010027476 Metastases Diseases 0.000 description 3
- 206010061309 Neoplasm progression Diseases 0.000 description 3
- 102000007399 Nuclear hormone receptor Human genes 0.000 description 3
- 108020005497 Nuclear hormone receptor Proteins 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 102100023085 Serine/threonine-protein kinase mTOR Human genes 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- 230000002159 abnormal effect Effects 0.000 description 3
- 230000005856 abnormality Effects 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 125000004442 acylamino group Chemical group 0.000 description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 230000033115 angiogenesis Effects 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 210000000601 blood cell Anatomy 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 239000007853 buffer solution Substances 0.000 description 3
- 239000001506 calcium phosphate Substances 0.000 description 3
- 235000011010 calcium phosphates Nutrition 0.000 description 3
- 230000004663 cell proliferation Effects 0.000 description 3
- 230000005754 cellular signaling Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 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 3
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 239000007884 disintegrant Substances 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 229940088597 hormone Drugs 0.000 description 3
- 239000005556 hormone Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 3
- 210000004072 lung Anatomy 0.000 description 3
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
- 230000003211 malignant effect Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 206010061289 metastatic neoplasm Diseases 0.000 description 3
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 3
- 125000002971 oxazolyl group Chemical group 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 235000018102 proteins Nutrition 0.000 description 3
- 125000002098 pyridazinyl group Chemical group 0.000 description 3
- 238000007390 skin biopsy Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- 150000008163 sugars Chemical class 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- 125000000335 thiazolyl group Chemical group 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 238000002877 time resolved fluorescence resonance energy transfer Methods 0.000 description 3
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 3
- 230000005751 tumor progression Effects 0.000 description 3
- 231100000402 unacceptable toxicity Toxicity 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- ZAEAHBWLSUALDG-MRXNPFEDSA-N (3r)-3-(cyclohexylmethyl)-6-[4-(1h-1,2,4-triazol-5-yl)phenyl]-3,4-dihydro-1h-pyrazino[2,3-b]pyrazin-2-one Chemical compound C([C@H]1NC2=NC(=CN=C2NC1=O)C=1C=CC(=CC=1)C=1NN=CN=1)C1CCCCC1 ZAEAHBWLSUALDG-MRXNPFEDSA-N 0.000 description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 2
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 2
- YMTNFIVNOUHQSD-UHFFFAOYSA-N 2-(4-cyanophenyl)-8-oxo-9-phenyl-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=CC(=CC=3)C#N)=NC=2N1C1=CC=CC=C1 YMTNFIVNOUHQSD-UHFFFAOYSA-N 0.000 description 2
- IZBPPYCCPMSLQI-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-8-[(3-methoxyphenyl)methyl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound COC1=CC=CC(CN2C3=NC(=CN=C3NC(=O)C2)C=2C=CC(O)=CC=2)=C1 IZBPPYCCPMSLQI-UHFFFAOYSA-N 0.000 description 2
- VVBJUWBGVSHSFS-UHFFFAOYSA-N 2-(4-nitrophenyl)-8-oxo-9-phenyl-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=CC(=CC=3)[N+]([O-])=O)=NC=2N1C1=CC=CC=C1 VVBJUWBGVSHSFS-UHFFFAOYSA-N 0.000 description 2
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- CZUXUTZOEIRAGY-UHFFFAOYSA-N 2-methyl-8-oxo-9-phenyl-7h-purine-6-carboxamide Chemical compound C12=NC(C)=NC(C(N)=O)=C2NC(=O)N1C1=CC=CC=C1 CZUXUTZOEIRAGY-UHFFFAOYSA-N 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
- XUUDRYNLHCRUEM-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-5-[(3-methoxyphenyl)methyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound COC1=CC=CC(CN2C3=NC(=CN=C3NCC2=O)C=2C=CC(O)=CC=2)=C1 XUUDRYNLHCRUEM-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
- ZAEAHBWLSUALDG-UHFFFAOYSA-N 3-(cyclohexylmethyl)-6-[4-(1h-1,2,4-triazol-5-yl)phenyl]-3,4-dihydro-1h-pyrazino[2,3-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=CC(=CC=3)C=3NN=CN=3)N=C2NC1CC1CCCCC1 ZAEAHBWLSUALDG-UHFFFAOYSA-N 0.000 description 2
- FTMIABDXGIBHQJ-CYBMUJFWSA-N 3-[(1r)-1-phenylethyl]-5-[4-(1h-1,2,4-triazol-5-yl)phenyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1([C@@H](C)N2C(NC3=NC=C(N=C32)C=2C=CC(=CC=2)C2=NNC=N2)=O)=CC=CC=C1 FTMIABDXGIBHQJ-CYBMUJFWSA-N 0.000 description 2
- FTMIABDXGIBHQJ-ZDUSSCGKSA-N 3-[(1s)-1-phenylethyl]-5-[4-(1h-1,2,4-triazol-5-yl)phenyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1([C@H](C)N2C(NC3=NC=C(N=C32)C=2C=CC(=CC=2)C=2NC=NN=2)=O)=CC=CC=C1 FTMIABDXGIBHQJ-ZDUSSCGKSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 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
- UQWCGQMOZDHUNF-UHFFFAOYSA-N 5-[4-(1h-imidazol-2-yl)phenyl]-3-[2-(oxan-4-yl)ethyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=CC(=CC=3)C=3NC=CN=3)N=C2N1CCC1CCOCC1 UQWCGQMOZDHUNF-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
- DXHKTHGKGVIGTC-UHFFFAOYSA-N 9-(2-hydroxyethyl)-2-(trifluoromethyl)purine-6-carboxamide Chemical compound NC(=O)C1=NC(C(F)(F)F)=NC2=C1N=CN2CCO DXHKTHGKGVIGTC-UHFFFAOYSA-N 0.000 description 2
- MWKDGWKQVQCNGG-UHFFFAOYSA-N 9-(2-hydroxyethyl)-2-phenylpurine-6-carboxamide Chemical compound N=1C=2N(CCO)C=NC=2C(C(=O)N)=NC=1C1=CC=CC=C1 MWKDGWKQVQCNGG-UHFFFAOYSA-N 0.000 description 2
- FBECNQNZSXSUKI-UHFFFAOYSA-N 9-(2-hydroxyethyl)-2-prop-1-enylpurine-6-carboxamide Chemical compound CC=CC1=NC(C(N)=O)=C2N=CN(CCO)C2=N1 FBECNQNZSXSUKI-UHFFFAOYSA-N 0.000 description 2
- QVVNOYDJHDGIMD-UHFFFAOYSA-N 9-(3-hydroxypropyl)-2-(trifluoromethyl)purine-6-carboxamide Chemical compound NC(=O)C1=NC(C(F)(F)F)=NC2=C1N=CN2CCCO QVVNOYDJHDGIMD-UHFFFAOYSA-N 0.000 description 2
- FPQGZRGCTSQXCL-UHFFFAOYSA-N 9-(3-hydroxypropyl)-2-methylpurine-6-carboxamide Chemical compound CC1=NC(C(N)=O)=C2N=CN(CCCO)C2=N1 FPQGZRGCTSQXCL-UHFFFAOYSA-N 0.000 description 2
- FPIZONCOBWJNNC-JJNLEZRASA-N 9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-methylpurine-6-carboxamide Chemical compound C12=NC(C)=NC(C(N)=O)=C2N=CN1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O FPIZONCOBWJNNC-JJNLEZRASA-N 0.000 description 2
- GNCVUNHMILWMNF-UHFFFAOYSA-N 9-benzyl-2-(4-methoxyphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=NC(C(N)=O)=C(NC(=O)N2CC=3C=CC=CC=3)C2=N1 GNCVUNHMILWMNF-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-OUBTZVSYSA-N Ammonia-15N Chemical compound [15NH3] QGZKDVFQNNGYKY-OUBTZVSYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 206010007270 Carcinoid syndrome Diseases 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- HKVAMNSJSFKALM-GKUWKFKPSA-N Everolimus Chemical compound C1C[C@@H](OCCO)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 HKVAMNSJSFKALM-GKUWKFKPSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 229930091371 Fructose Natural products 0.000 description 2
- 239000005715 Fructose Substances 0.000 description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 241000287828 Gallus gallus Species 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- 208000008839 Kidney Neoplasms Diseases 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 2
- 150000001204 N-oxides Chemical class 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
- 241001494479 Pecora Species 0.000 description 2
- 241000286209 Phasianidae Species 0.000 description 2
- 108010064218 Poly (ADP-Ribose) Polymerase-1 Proteins 0.000 description 2
- 102100023712 Poly [ADP-ribose] polymerase 1 Human genes 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- 206010038389 Renal cancer Diseases 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- JEIVYJHYJKISIY-UHFFFAOYSA-N [2-(benzoyloxymethyl)-3-(6-carbamoyl-2-methylpurin-9-yl)cyclobutyl]methyl benzoate Chemical compound C12=NC(C)=NC(C(N)=O)=C2N=CN1C(C1COC(=O)C=2C=CC=CC=2)CC1COC(=O)C1=CC=CC=C1 JEIVYJHYJKISIY-UHFFFAOYSA-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
- 230000009471 action Effects 0.000 description 2
- 125000005426 adeninyl group Chemical group N1=C(N=C2N=CNC2=C1N)* 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000000783 alginic acid Substances 0.000 description 2
- 229960001126 alginic acid Drugs 0.000 description 2
- 150000004781 alginic acids Chemical class 0.000 description 2
- 125000005262 alkoxyamine group Chemical group 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000001409 amidines Chemical class 0.000 description 2
- 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000005602 azabenzimidazolyl group Chemical group 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000005872 benzooxazolyl group Chemical group 0.000 description 2
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 210000000988 bone and bone Anatomy 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 229910000389 calcium phosphate Inorganic materials 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000033077 cellular process Effects 0.000 description 2
- 239000007910 chewable tablet Substances 0.000 description 2
- 229940110456 cocoa butter Drugs 0.000 description 2
- 235000019868 cocoa butter Nutrition 0.000 description 2
- 238000003927 comet assay Methods 0.000 description 2
- DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 229910052805 deuterium Inorganic materials 0.000 description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000004064 dysfunction Effects 0.000 description 2
- 150000002081 enamines Chemical class 0.000 description 2
- 229960005167 everolimus Drugs 0.000 description 2
- 230000005713 exacerbation Effects 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 230000037406 food intake Effects 0.000 description 2
- 235000012631 food intake Nutrition 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 229920001903 high density polyethylene Polymers 0.000 description 2
- 239000004700 high-density polyethylene Substances 0.000 description 2
- 150000007857 hydrazones Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 125000002632 imidazolidinyl group Chemical group 0.000 description 2
- 125000002636 imidazolinyl group Chemical group 0.000 description 2
- 125000005945 imidazopyridyl group Chemical group 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 201000010982 kidney cancer Diseases 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 230000001394 metastastic effect Effects 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 125000002757 morpholinyl group Chemical group 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 2
- 239000002777 nucleoside Substances 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 125000000394 phosphonato group Chemical group [O-]P([O-])(*)=O 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 208000029340 primitive neuroectodermal tumor Diseases 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 239000003909 protein kinase inhibitor Substances 0.000 description 2
- 230000009822 protein phosphorylation Effects 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000006085 pyrrolopyridyl group Chemical group 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 230000002285 radioactive effect Effects 0.000 description 2
- 230000000306 recurrent effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000002271 resection Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 230000003248 secreting effect Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000011301 standard therapy Methods 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 239000002511 suppository base Substances 0.000 description 2
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 2
- 125000004927 thianaphthalenyl group Chemical group S1C(C=CC2=CC=CC=C12)* 0.000 description 2
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- 230000003442 weekly effect Effects 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- 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
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- 108091032973 (ribonucleotides)n+m Proteins 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
- RAMUKMWOTXRIBZ-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-(2-oxo-1,3-dihydroimidazo[4,5-b]pyridin-6-yl)naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CN=C(NC(=O)N2)C2=C1 RAMUKMWOTXRIBZ-UHFFFAOYSA-N 0.000 description 1
- RGIRAMBPYYWIFF-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-(2-oxo-3,4-dihydro-1h-pyrido[2,3-b]pyrazin-7-yl)naphthalen-1-yl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1C1=CN=C(NCC(=O)N2)C2=C1 RGIRAMBPYYWIFF-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
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 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
- PDYMCBRGMDRAPX-UHFFFAOYSA-N 1-methyl-6-phenyl-3h-imidazo[4,5-b]pyridin-2-one Chemical compound C=1N=C2NC(=O)N(C)C2=CC=1C1=CC=CC=C1 PDYMCBRGMDRAPX-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-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
- CKFTYQGQPXAMLA-UHFFFAOYSA-N 1h-pyrazino[2,3-b]pyrazin-2-one Chemical compound C1=CN=C2NC(=O)C=NC2=N1 CKFTYQGQPXAMLA-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 class 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 class 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
- CTTXAKKCMQVQOY-UHFFFAOYSA-N 2-(3-carbamoylphenyl)-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(C=CC=3)C(N)=O)N=C21 CTTXAKKCMQVQOY-UHFFFAOYSA-N 0.000 description 1
- XSPKQLPEYNLKJR-UHFFFAOYSA-N 2-(3-cyanophenyl)-8-oxo-9-phenyl-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=C(C=CC=3)C#N)=NC=2N1C1=CC=CC=C1 XSPKQLPEYNLKJR-UHFFFAOYSA-N 0.000 description 1
- GFOPGIMPJRXOJI-UHFFFAOYSA-N 2-(3-cyanophenyl)-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(C=CC=3)C#N)N=C21 GFOPGIMPJRXOJI-UHFFFAOYSA-N 0.000 description 1
- QLYCEOLYVLXKTJ-UHFFFAOYSA-N 2-(3-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=C(O)C=CC=3)N=C21 QLYCEOLYVLXKTJ-UHFFFAOYSA-N 0.000 description 1
- VKBNVPXLCNOFDA-UHFFFAOYSA-N 2-(3-hydroxyanilino)-9-(2-methoxyphenyl)purine-6-carboxamide Chemical compound COC1=CC=CC=C1N1C2=NC(NC=3C=C(O)C=CC=3)=NC(C(N)=O)=C2N=C1 VKBNVPXLCNOFDA-UHFFFAOYSA-N 0.000 description 1
- VHSIMIJLYOSVGV-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-8-oxo-9-(2-phenoxyphenyl)-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=C(O)C=CC=3)=NC=2N1C1=CC=CC=C1OC1=CC=CC=C1 VHSIMIJLYOSVGV-UHFFFAOYSA-N 0.000 description 1
- SYSDHTKNMONKFW-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-8-oxo-9-(2-phenylphenyl)-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=C(O)C=CC=3)=NC=2N1C1=CC=CC=C1C1=CC=CC=C1 SYSDHTKNMONKFW-UHFFFAOYSA-N 0.000 description 1
- TTZKZDUNODWIBB-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-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=C(O)C=CC=3)N=C21 TTZKZDUNODWIBB-UHFFFAOYSA-N 0.000 description 1
- LPMDNFVSAQNCQG-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-8-oxo-9-(5,6,7,8-tetrahydronaphthalen-1-yl)-7h-purine-6-carboxamide Chemical compound N=1C=2N(C=3C=4CCCCC=4C=CC=3)C(=O)NC=2C(C(=O)N)=NC=1C1=CC=CC(O)=C1 LPMDNFVSAQNCQG-UHFFFAOYSA-N 0.000 description 1
- YMGAPOQTCLXGMJ-SECBINFHSA-N 2-(3-hydroxyphenyl)-8-oxo-9-[(3r)-oxolan-3-yl]-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=C(O)C=CC=3)=NC=2N1[C@@H]1CCOC1 YMGAPOQTCLXGMJ-SECBINFHSA-N 0.000 description 1
- YMGAPOQTCLXGMJ-VIFPVBQESA-N 2-(3-hydroxyphenyl)-8-oxo-9-[(3s)-oxolan-3-yl]-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=C(O)C=CC=3)=NC=2N1[C@H]1CCOC1 YMGAPOQTCLXGMJ-VIFPVBQESA-N 0.000 description 1
- LQFLMRXTJJJEHH-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-8-oxo-9-[2-(trifluoromethoxy)phenyl]-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=C(O)C=CC=3)=NC=2N1C1=CC=CC=C1OC(F)(F)F LQFLMRXTJJJEHH-UHFFFAOYSA-N 0.000 description 1
- NRHZZSMMYHWNAH-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-8-oxo-9-[2-(trifluoromethyl)phenyl]-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=C(O)C=CC=3)=NC=2N1C1=CC=CC=C1C(F)(F)F NRHZZSMMYHWNAH-UHFFFAOYSA-N 0.000 description 1
- QGZDJMKGWDHOEG-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-8-oxo-9-[4-(trifluoromethyl)phenyl]-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=C(O)C=CC=3)=NC=2N1C1=CC=C(C(F)(F)F)C=C1 QGZDJMKGWDHOEG-UHFFFAOYSA-N 0.000 description 1
- GTXXPRDATLNTGI-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-8-oxo-9-piperidin-4-yl-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=C(O)C=CC=3)=NC=2N1C1CCNCC1 GTXXPRDATLNTGI-UHFFFAOYSA-N 0.000 description 1
- AIOXKFRBCMOLSO-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-8-oxo-9-propan-2-yl-7h-purine-6-carboxamide Chemical compound N=1C(C(N)=O)=C2NC(=O)N(C(C)C)C2=NC=1C1=CC=CC(O)=C1 AIOXKFRBCMOLSO-UHFFFAOYSA-N 0.000 description 1
- LCASKMOOXITUEC-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-9-(1h-indol-4-yl)-8-oxo-7h-purine-6-carboxamide Chemical compound N=1C=2N(C=3C=4C=CNC=4C=CC=3)C(=O)NC=2C(C(=O)N)=NC=1C1=CC=CC(O)=C1 LCASKMOOXITUEC-UHFFFAOYSA-N 0.000 description 1
- REKXWQDSPQOUAG-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-9-(2-methoxyphenyl)purine-6-carboxamide Chemical compound COC1=CC=CC=C1N1C2=NC(C=3C=C(O)C=CC=3)=NC(C(N)=O)=C2N=C1 REKXWQDSPQOUAG-UHFFFAOYSA-N 0.000 description 1
- HQQCFXVFWQOFEI-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-9-(2-methylphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound CC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C(O)C=CC=3)N=C21 HQQCFXVFWQOFEI-UHFFFAOYSA-N 0.000 description 1
- UCIWKRFNWOZMJV-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-9-(2-methylpropyl)-8-oxo-7h-purine-6-carboxamide Chemical compound N=1C(C(N)=O)=C2NC(=O)N(CC(C)C)C2=NC=1C1=CC=CC(O)=C1 UCIWKRFNWOZMJV-UHFFFAOYSA-N 0.000 description 1
- HCNZVXYIFJUNLB-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-9-(4-methoxy-2-methylphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound CC1=CC(OC)=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C(O)C=CC=3)N=C21 HCNZVXYIFJUNLB-UHFFFAOYSA-N 0.000 description 1
- ODUHNOHLJKOZSD-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-9-(4-methoxyphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound C1=CC(OC)=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C(O)C=CC=3)N=C21 ODUHNOHLJKOZSD-UHFFFAOYSA-N 0.000 description 1
- DPVDUYVOIBIITN-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-9-(oxan-4-yl)-8-oxo-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=C(O)C=CC=3)=NC=2N1C1CCOCC1 DPVDUYVOIBIITN-UHFFFAOYSA-N 0.000 description 1
- XGGDQIKSONBGRL-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-9-(oxan-4-ylmethyl)-8-oxo-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=C(O)C=CC=3)=NC=2N1CC1CCOCC1 XGGDQIKSONBGRL-UHFFFAOYSA-N 0.000 description 1
- WNCITCOJMDPTFX-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-9-[2-(2-methylpropyl)phenyl]-8-oxo-7h-purine-6-carboxamide Chemical compound CC(C)CC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C(O)C=CC=3)N=C21 WNCITCOJMDPTFX-UHFFFAOYSA-N 0.000 description 1
- XRNLNXMBIPHBES-UHFFFAOYSA-N 2-(3h-benzimidazol-5-yl)-3h-benzimidazole-5-carboxamide Chemical compound C1=C2NC=NC2=CC(C=2NC3=CC=C(C=C3N=2)C(=O)N)=C1 XRNLNXMBIPHBES-UHFFFAOYSA-N 0.000 description 1
- UOIKQIVKKRHYNK-UHFFFAOYSA-N 2-(3h-benzimidazol-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=C4NC=NC4=CC=3)N=C21 UOIKQIVKKRHYNK-UHFFFAOYSA-N 0.000 description 1
- CUKNHBIKUAOGMV-UHFFFAOYSA-N 2-(3h-benzimidazol-5-yl)-9-(2-fluorophenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=C4NC=NC4=CC=3)=NC=2N1C1=CC=CC=C1F CUKNHBIKUAOGMV-UHFFFAOYSA-N 0.000 description 1
- SYPYBDBWXVNCMN-UHFFFAOYSA-N 2-(3h-benzimidazol-5-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=CC=3)N=C21 SYPYBDBWXVNCMN-UHFFFAOYSA-N 0.000 description 1
- FMVQDRMKUKTEHK-UHFFFAOYSA-N 2-(3h-benzimidazol-5-yl)-9-cyclohexyl-8-oxo-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=C4NC=NC4=CC=3)=NC=2N1C1CCCCC1 FMVQDRMKUKTEHK-UHFFFAOYSA-N 0.000 description 1
- VRDNYMBILTXNLL-UHFFFAOYSA-N 2-(4-carbamoylphenyl)-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=CC(=CC=3)C(N)=O)N=C21 VRDNYMBILTXNLL-UHFFFAOYSA-N 0.000 description 1
- IXSSFPKPRMAVNQ-UHFFFAOYSA-N 2-(4-chloropyridin-3-yl)-8-oxo-9-[2-(trifluoromethyl)phenyl]-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C(=CC=NC=3)Cl)=NC=2N1C1=CC=CC=C1C(F)(F)F IXSSFPKPRMAVNQ-UHFFFAOYSA-N 0.000 description 1
- YGKQCJUCIVSDMR-UHFFFAOYSA-N 2-(4-cyanophenyl)-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=CC(=CC=3)C#N)N=C21 YGKQCJUCIVSDMR-UHFFFAOYSA-N 0.000 description 1
- PFLNNBRHCLLGHO-UHFFFAOYSA-N 2-(4-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(O)=CC=3)N=C21 PFLNNBRHCLLGHO-UHFFFAOYSA-N 0.000 description 1
- XIHROTCGKRDGKR-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-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=CC(O)=CC=3)N=C21 XIHROTCGKRDGKR-UHFFFAOYSA-N 0.000 description 1
- AIDNXLGIWLGQDQ-UHFFFAOYSA-N 2-(4-imidazol-1-ylphenyl)-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=CC(=CC=3)N3C=NC=C3)N=C21 AIDNXLGIWLGQDQ-UHFFFAOYSA-N 0.000 description 1
- OYKNWIDIIHMSKR-UHFFFAOYSA-N 2-(5-chloropyridin-3-yl)-8-oxo-9-[2-(trifluoromethyl)phenyl]-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=C(Cl)C=NC=3)=NC=2N1C1=CC=CC=C1C(F)(F)F OYKNWIDIIHMSKR-UHFFFAOYSA-N 0.000 description 1
- RDMDYUQDKJPRED-UHFFFAOYSA-N 2-(5-fluoropyridin-3-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=C(F)C=NC=3)N=C21 RDMDYUQDKJPRED-UHFFFAOYSA-N 0.000 description 1
- JWGOSMIWSZNTEA-UHFFFAOYSA-N 2-(7-methyl-3h-benzimidazol-5-yl)-8-[2-(oxan-4-yl)ethyl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C=1C=2NC=NC=2C(C)=CC=1C(N=C12)=CN=C1NC(=O)CN2CCC1CCOCC1 JWGOSMIWSZNTEA-UHFFFAOYSA-N 0.000 description 1
- RSIHMCRNLBDGEN-UHFFFAOYSA-N 2-(8-oxo-2-phenyl-7h-purin-9-yl)acetic acid Chemical compound N=1C=C2NC(=O)N(CC(=O)O)C2=NC=1C1=CC=CC=C1 RSIHMCRNLBDGEN-UHFFFAOYSA-N 0.000 description 1
- FMZCZAVHZRAHRB-UHFFFAOYSA-N 2-(benzimidazol-1-yl)-9-(2-methoxyphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(N3C4=CC=CC=C4N=C3)N=C21 FMZCZAVHZRAHRB-UHFFFAOYSA-N 0.000 description 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
- KQTHSEWLOBJIOZ-UHFFFAOYSA-N 2-[2-(hydroxymethyl)anilino]-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)CO)N=C21 KQTHSEWLOBJIOZ-UHFFFAOYSA-N 0.000 description 1
- UZUWXKYUGWKVFP-UHFFFAOYSA-N 2-[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=C3NCC(=O)NC3=NC=2)C(C)=CC=1C1=NN=CN1 UZUWXKYUGWKVFP-UHFFFAOYSA-N 0.000 description 1
- MQKOPINQZVDCFE-UHFFFAOYSA-N 2-[2-methyl-4-(1h-1,2,4-triazol-5-yl)phenyl]-8-[2-(oxan-4-yl)ethyl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound CC1=CC(C=2NC=NN=2)=CC=C1C(N=C12)=CN=C1NC(=O)CN2CCC1CCOCC1 MQKOPINQZVDCFE-UHFFFAOYSA-N 0.000 description 1
- MLEUAHJZHFABNI-UHFFFAOYSA-N 2-[2-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-8-(oxan-4-ylmethyl)-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound CC1=NC(C=2NC=NN=2)=CC=C1C(N=C12)=CN=C1NC(=O)CN2CC1CCOCC1 MLEUAHJZHFABNI-UHFFFAOYSA-N 0.000 description 1
- RBLRRVZXUXIHNG-UHFFFAOYSA-N 2-[2-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-8-[2-(oxan-4-yl)ethyl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound CC1=NC(C=2NC=NN=2)=CC=C1C(N=C12)=CN=C1NC(=O)CN2CCC1CCOCC1 RBLRRVZXUXIHNG-UHFFFAOYSA-N 0.000 description 1
- BGTLIODMWIWDTM-UHFFFAOYSA-N 2-[3-(aminomethyl)phenyl]-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(CN)C=CC=3)N=C21 BGTLIODMWIWDTM-UHFFFAOYSA-N 0.000 description 1
- RLVWQYYMNVREPW-UHFFFAOYSA-N 2-[3-(hydroxymethyl)anilino]-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=C(CO)C=CC=3)N=C21 RLVWQYYMNVREPW-UHFFFAOYSA-N 0.000 description 1
- RPFKJQXAUBYMLL-UHFFFAOYSA-N 2-[3-fluoro-2-methyl-4-(1h-1,2,4-triazol-5-yl)phenyl]-8-(oxan-4-yl)-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound CC1=C(F)C(C2=NNC=N2)=CC=C1C(N=C12)=CN=C1NC(=O)CN2C1CCOCC1 RPFKJQXAUBYMLL-UHFFFAOYSA-N 0.000 description 1
- KDNANMZVIXBBHI-UHFFFAOYSA-N 2-[3-fluoro-2-methyl-4-(1h-1,2,4-triazol-5-yl)phenyl]-8-[2-(oxan-4-yl)ethyl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound CC1=C(F)C(C=2NC=NN=2)=CC=C1C(N=C12)=CN=C1NC(=O)CN2CCC1CCOCC1 KDNANMZVIXBBHI-UHFFFAOYSA-N 0.000 description 1
- XCAKYWRPAFRUKL-UHFFFAOYSA-N 2-[3-fluoro-4-(1h-1,2,4-triazol-5-yl)phenyl]-8-(2-methoxyethyl)-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CCOC)CC(=O)NC2=NC=C1C(C=C1F)=CC=C1C1=NN=CN1 XCAKYWRPAFRUKL-UHFFFAOYSA-N 0.000 description 1
- VQOJDNXHKRRVKG-UHFFFAOYSA-N 2-[3-fluoro-4-(1h-1,2,4-triazol-5-yl)phenyl]-8-[2-(oxan-4-yl)ethyl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound FC1=CC(C=2N=C3N(CCC4CCOCC4)CC(=O)NC3=NC=2)=CC=C1C1=NN=CN1 VQOJDNXHKRRVKG-UHFFFAOYSA-N 0.000 description 1
- OSCZBKPQIHRLCX-UHFFFAOYSA-N 2-[4-(1h-1,2,4-triazol-5-yl)phenyl]-8-[[3-(trifluoromethyl)phenyl]methyl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound FC(F)(F)C1=CC=CC(CN2C3=NC(=CN=C3NC(=O)C2)C=2C=CC(=CC=2)C=2NC=NN=2)=C1 OSCZBKPQIHRLCX-UHFFFAOYSA-N 0.000 description 1
- MLZCJYBETXZLIO-UHFFFAOYSA-N 2-[4-(1h-imidazol-2-yl)phenyl]-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=CC(=CC=3)C=3NC=CN=3)N=C21 MLZCJYBETXZLIO-UHFFFAOYSA-N 0.000 description 1
- BPXGEUALTFPZOM-UHFFFAOYSA-N 2-[4-(2-hydroxypropan-2-yl)phenyl]-8-(oxan-4-ylmethyl)-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=CC(C(C)(O)C)=CC=C1C1=CN=C(NC(=O)CN2CC3CCOCC3)C2=N1 BPXGEUALTFPZOM-UHFFFAOYSA-N 0.000 description 1
- NJXKFIOLXCRUCQ-UHFFFAOYSA-N 2-[4-(2-hydroxypropan-2-yl)phenyl]-8-[2-(oxan-4-yl)ethyl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=CC(C(C)(O)C)=CC=C1C1=CN=C(NC(=O)CN2CCC3CCOCC3)C2=N1 NJXKFIOLXCRUCQ-UHFFFAOYSA-N 0.000 description 1
- WVOFKVNZEAXIKU-UHFFFAOYSA-N 2-[4-(5-methyl-1h-1,2,4-triazol-3-yl)phenyl]-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=CC(=CC=3)C=3NC(C)=NN=3)N=C21 WVOFKVNZEAXIKU-UHFFFAOYSA-N 0.000 description 1
- BVNVZYCZFQGDFQ-UHFFFAOYSA-N 2-[4-(aminomethyl)phenyl]-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=CC(CN)=CC=3)N=C21 BVNVZYCZFQGDFQ-UHFFFAOYSA-N 0.000 description 1
- YTXQZTBVBLMJBQ-UHFFFAOYSA-N 2-[4-[3-(cyclohexylmethyl)-2-oxo-1h-imidazo[4,5-b]pyrazin-5-yl]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1C1=CN=C(NC(=O)N2CC3CCCCC3)C2=N1 YTXQZTBVBLMJBQ-UHFFFAOYSA-N 0.000 description 1
- BDYYRVQPWCHOGW-UHFFFAOYSA-N 2-[4-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-8-(oxan-4-ylmethyl)-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound CC1=CC(C2=NNC=N2)=NC=C1C(N=C12)=CN=C1NC(=O)CN2CC1CCOCC1 BDYYRVQPWCHOGW-UHFFFAOYSA-N 0.000 description 1
- MGLOYVHEYOOETR-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-4-(1h-1,2,4-triazol-5-yl)phenyl]-8-(oxan-4-yl)-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound FC=1C=C(C=2N=C3N(C4CCOCC4)CC(=O)NC3=NC=2)C(C)=CC=1C=1N=CNN=1 MGLOYVHEYOOETR-UHFFFAOYSA-N 0.000 description 1
- HLKYWXBABQWMDJ-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-4-(1h-1,2,4-triazol-5-yl)phenyl]-8-propan-2-yl-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(C(C)C)CC(=O)NC2=NC=C1C(C(=C1)C)=CC(F)=C1C=1N=CNN=1 HLKYWXBABQWMDJ-UHFFFAOYSA-N 0.000 description 1
- KQVBDNFZBDBYCA-UHFFFAOYSA-N 2-[6-(2-hydroxypropan-2-yl)-2-methylpyridin-3-yl]-8-(oxan-4-ylmethyl)-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound CC1=NC(C(C)(C)O)=CC=C1C1=CN=C(NC(=O)CN2CC3CCOCC3)C2=N1 KQVBDNFZBDBYCA-UHFFFAOYSA-N 0.000 description 1
- DAAFDFKJLGHFBQ-UHFFFAOYSA-N 2-[6-(2-hydroxypropan-2-yl)-4-methylpyridin-3-yl]-8-(oxan-4-ylmethyl)-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound CC1=CC(C(C)(C)O)=NC=C1C1=CN=C(NC(=O)CN2CC3CCOCC3)C2=N1 DAAFDFKJLGHFBQ-UHFFFAOYSA-N 0.000 description 1
- NJPJPESOUGQOMJ-UHFFFAOYSA-N 2-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-8-(2-methoxyethyl)-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CCOC)CC(=O)NC2=NC=C1C1=CC=C(C(C)(C)O)N=C1 NJPJPESOUGQOMJ-UHFFFAOYSA-N 0.000 description 1
- TYAMMNKVQSFFRX-UHFFFAOYSA-N 2-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-8-(2-methylpropyl)-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CC(C)C)CC(=O)NC2=NC=C1C1=CC=C(C(C)(C)O)N=C1 TYAMMNKVQSFFRX-UHFFFAOYSA-N 0.000 description 1
- GXKVTFYWASGFEH-UHFFFAOYSA-N 2-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-8-(2-morpholin-4-ylethyl)-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NC(=O)CN2CCN3CCOCC3)C2=N1 GXKVTFYWASGFEH-UHFFFAOYSA-N 0.000 description 1
- BLYAPPOKCOQUMX-UHFFFAOYSA-N 2-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-8-(2-phenylethyl)-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NC(=O)CN2CCC=3C=CC=CC=3)C2=N1 BLYAPPOKCOQUMX-UHFFFAOYSA-N 0.000 description 1
- CBIIYNCVOYUQDQ-UHFFFAOYSA-N 2-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-8-(3-methoxypropyl)-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CCCOC)CC(=O)NC2=NC=C1C1=CC=C(C(C)(C)O)N=C1 CBIIYNCVOYUQDQ-UHFFFAOYSA-N 0.000 description 1
- IBHHJGZOOHWZKC-UHFFFAOYSA-N 2-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-8-(oxan-4-yl)-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NC(=O)CN2C3CCOCC3)C2=N1 IBHHJGZOOHWZKC-UHFFFAOYSA-N 0.000 description 1
- UWUPKVZQISLSSA-UHFFFAOYSA-N 2-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-8-(oxan-4-ylmethyl)-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NC(=O)CN2CC3CCOCC3)C2=N1 UWUPKVZQISLSSA-UHFFFAOYSA-N 0.000 description 1
- RRSHKGLMZARSTK-UHFFFAOYSA-N 2-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-8-(oxolan-3-ylmethyl)-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NC(=O)CN2CC3COCC3)C2=N1 RRSHKGLMZARSTK-UHFFFAOYSA-N 0.000 description 1
- CXWODWYNTIZYON-ZIAGYGMSSA-N 2-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-8-[(1r,3r)-3-methoxycyclopentyl]-5,7-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=C2NC(=O)C1 CXWODWYNTIZYON-ZIAGYGMSSA-N 0.000 description 1
- CXWODWYNTIZYON-KGLIPLIRSA-N 2-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-8-[(1r,3s)-3-methoxycyclopentyl]-5,7-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=C2NC(=O)C1 CXWODWYNTIZYON-KGLIPLIRSA-N 0.000 description 1
- CXWODWYNTIZYON-UONOGXRCSA-N 2-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-8-[(1s,3r)-3-methoxycyclopentyl]-5,7-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=C2NC(=O)C1 CXWODWYNTIZYON-UONOGXRCSA-N 0.000 description 1
- CXWODWYNTIZYON-KBPBESRZSA-N 2-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-8-[(1s,3s)-3-methoxycyclopentyl]-5,7-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=C2NC(=O)C1 CXWODWYNTIZYON-KBPBESRZSA-N 0.000 description 1
- TUHJKXZTDPWLDV-GFCCVEGCSA-N 2-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-8-[(3r)-oxolan-3-yl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NC(=O)CN2[C@H]3COCC3)C2=N1 TUHJKXZTDPWLDV-GFCCVEGCSA-N 0.000 description 1
- TUHJKXZTDPWLDV-LBPRGKRZSA-N 2-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-8-[(3s)-oxolan-3-yl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NC(=O)CN2[C@@H]3COCC3)C2=N1 TUHJKXZTDPWLDV-LBPRGKRZSA-N 0.000 description 1
- VGYOLLKVSKNHQS-CYBMUJFWSA-N 2-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-8-[[(2r)-oxolan-2-yl]methyl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NC(=O)CN2C[C@@H]3OCCC3)C2=N1 VGYOLLKVSKNHQS-CYBMUJFWSA-N 0.000 description 1
- VGYOLLKVSKNHQS-ZDUSSCGKSA-N 2-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-8-[[(2s)-oxolan-2-yl]methyl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NC(=O)CN2C[C@H]3OCCC3)C2=N1 VGYOLLKVSKNHQS-ZDUSSCGKSA-N 0.000 description 1
- NUFDTTCJPSICSY-UHFFFAOYSA-N 2-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-8-[[3-(trifluoromethyl)phenyl]methyl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NC(=O)CN2CC=3C=C(C=CC=3)C(F)(F)F)C2=N1 NUFDTTCJPSICSY-UHFFFAOYSA-N 0.000 description 1
- KWZWONSVPZJSDW-UHFFFAOYSA-N 2-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-8-phenyl-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NC(=O)CN2C=3C=CC=CC=3)C2=N1 KWZWONSVPZJSDW-UHFFFAOYSA-N 0.000 description 1
- XBTBXISVXWQPKC-UHFFFAOYSA-N 2-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-8-piperidin-4-yl-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NC(=O)CN2C3CCNCC3)C2=N1 XBTBXISVXWQPKC-UHFFFAOYSA-N 0.000 description 1
- KYDBWAOQRGEKAM-UHFFFAOYSA-N 2-[7-methyl-2-(methylamino)-3h-benzimidazol-5-yl]-8-[2-(oxan-4-yl)ethyl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=C2NC(NC)=NC2=C(C)C=C1C(N=C12)=CN=C1NC(=O)CN2CCC1CCOCC1 KYDBWAOQRGEKAM-UHFFFAOYSA-N 0.000 description 1
- OSBLTNPMIGYQGY-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetic acid;boric acid Chemical compound OB(O)O.OCC(N)(CO)CO.OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O OSBLTNPMIGYQGY-UHFFFAOYSA-N 0.000 description 1
- PPDPUIRKDSCCFN-UHFFFAOYSA-N 2-benzofuran-1,3-diimine Chemical compound C1=CC=C2C(=N)OC(=N)C2=C1 PPDPUIRKDSCCFN-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- UTPWCJLLRNTPEU-UHFFFAOYSA-N 2-cyclopentyl-9-(2-methoxyphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C3CCCC3)N=C21 UTPWCJLLRNTPEU-UHFFFAOYSA-N 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- DZNQOAQRVHCHDP-UHFFFAOYSA-N 2-phenyl-5h-pyrrolo[3,2-d]pyrimidine-4-carboxamide Chemical compound N=1C=2C=CNC=2C(C(=O)N)=NC=1C1=CC=CC=C1 DZNQOAQRVHCHDP-UHFFFAOYSA-N 0.000 description 1
- NVMATPIZWPTLIH-UHFFFAOYSA-N 2-phenyl-7,9-dihydropurin-8-one Chemical compound N1C=C2NC(=O)N=C2N=C1C1=CC=CC=C1 NVMATPIZWPTLIH-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- JQDISYRIHPZMLX-UHFFFAOYSA-N 3,3-dimethyl-6-[2-methyl-4-(1h-1,2,4-triazol-5-yl)phenyl]-1,4-dihydropyrazino[2,3-b]pyrazin-2-one Chemical compound C=1C=C(C=2N=C3NC(C)(C)C(=O)NC3=NC=2)C(C)=CC=1C1=NN=CN1 JQDISYRIHPZMLX-UHFFFAOYSA-N 0.000 description 1
- FIUYRRXZRKTKGS-UHFFFAOYSA-N 3,3-dimethyl-6-[2-methyl-4-(1h-1,2,4-triazol-5-yl)phenyl]-4-(oxan-4-ylmethyl)-1h-pyrazino[2,3-b]pyrazin-2-one Chemical compound CC1=CC(C=2NC=NN=2)=CC=C1C(N=C12)=CN=C1NC(=O)C(C)(C)N2CC1CCOCC1 FIUYRRXZRKTKGS-UHFFFAOYSA-N 0.000 description 1
- HPSIHXPEEQAULT-UHFFFAOYSA-N 3,3-dimethyl-6-[2-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-4-(oxan-4-ylmethyl)-1h-pyrazino[2,3-b]pyrazin-2-one Chemical compound CC1=NC(C=2NC=NN=2)=CC=C1C(N=C12)=CN=C1NC(=O)C(C)(C)N2CC1CCOCC1 HPSIHXPEEQAULT-UHFFFAOYSA-N 0.000 description 1
- KQFYZQKLUAHDHM-UHFFFAOYSA-N 3,3-dimethyl-6-[2-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-4-[2-(oxan-4-yl)ethyl]-1h-pyrazino[2,3-b]pyrazin-2-one Chemical compound CC1=NC(C=2NC=NN=2)=CC=C1C(N=C12)=CN=C1NC(=O)C(C)(C)N2CCC1CCOCC1 KQFYZQKLUAHDHM-UHFFFAOYSA-N 0.000 description 1
- SYHZXWIXJYELOD-UHFFFAOYSA-N 3,3-dimethyl-6-[4-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-4-(oxan-4-ylmethyl)-1h-pyrazino[2,3-b]pyrazin-2-one Chemical compound CC1=CC(C=2NC=NN=2)=NC=C1C(N=C12)=CN=C1NC(=O)C(C)(C)N2CC1CCOCC1 SYHZXWIXJYELOD-UHFFFAOYSA-N 0.000 description 1
- OQGUGVNMHJIMDB-UHFFFAOYSA-N 3-(1-morpholin-4-ylpropan-2-yl)-5-[4-(1h-1,2,4-triazol-5-yl)phenyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C12=NC(C=3C=CC(=CC=3)C=3NC=NN=3)=CN=C2NC(=O)N1C(C)CN1CCOCC1 OQGUGVNMHJIMDB-UHFFFAOYSA-N 0.000 description 1
- ZVFGWGFVLZSMCX-UHFFFAOYSA-N 3-(1-phenylethyl)-5-[4-(trifluoromethyl)phenyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C12=NC(C=3C=CC(=CC=3)C(F)(F)F)=CN=C2NC(=O)N1C(C)C1=CC=CC=C1 ZVFGWGFVLZSMCX-UHFFFAOYSA-N 0.000 description 1
- NUPHYZNYMCUIFJ-UHFFFAOYSA-N 3-(1-phenylethyl)-5-quinolin-4-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C12=NC(C=3C4=CC=CC=C4N=CC=3)=CN=C2NC(=O)N1C(C)C1=CC=CC=C1 NUPHYZNYMCUIFJ-UHFFFAOYSA-N 0.000 description 1
- KHUDFKOMPUTJHV-UHFFFAOYSA-N 3-(1-phenylethyl)-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C12=NC(C=3C4=CC=CN=C4C=CC=3)=CN=C2NC(=O)N1C(C)C1=CC=CC=C1 KHUDFKOMPUTJHV-UHFFFAOYSA-N 0.000 description 1
- LFUAZCRRROSASB-UHFFFAOYSA-N 3-(1-phenylethyl)-5-quinolin-5-yl-1h-imidazo[4,5-b]pyridin-2-one Chemical compound C12=NC(C=3C4=CC=CN=C4C=CC=3)=CC=C2NC(=O)N1C(C)C1=CC=CC=C1 LFUAZCRRROSASB-UHFFFAOYSA-N 0.000 description 1
- UBBKJGNWZDGODY-UHFFFAOYSA-N 3-(1-phenylethyl)-5-quinolin-5-yl-[1,3]oxazolo[4,5-b]pyrazin-2-one Chemical compound C12=NC(C=3C4=CC=CN=C4C=CC=3)=CN=C2OC(=O)N1C(C)C1=CC=CC=C1 UBBKJGNWZDGODY-UHFFFAOYSA-N 0.000 description 1
- KTEZHJVSVXJQGB-UHFFFAOYSA-N 3-(1-phenylethyl)-5-quinolin-6-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C12=NC(C=3C=C4C=CC=NC4=CC=3)=CN=C2NC(=O)N1C(C)C1=CC=CC=C1 KTEZHJVSVXJQGB-UHFFFAOYSA-N 0.000 description 1
- ZXWLCRFHAVKECN-UHFFFAOYSA-N 3-(1-pyridin-2-ylethyl)-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C12=NC(C=3C4=CC=CN=C4C=CC=3)=CN=C2NC(=O)N1C(C)C1=CC=CC=N1 ZXWLCRFHAVKECN-UHFFFAOYSA-N 0.000 description 1
- YGOQGSKPVMZXPJ-UHFFFAOYSA-N 3-(1-pyridin-3-ylethyl)-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C12=NC(C=3C4=CC=CN=C4C=CC=3)=CN=C2NC(=O)N1C(C)C1=CC=CN=C1 YGOQGSKPVMZXPJ-UHFFFAOYSA-N 0.000 description 1
- BOKZGMLRHMVLAI-UHFFFAOYSA-N 3-(1-pyridin-4-ylethyl)-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C12=NC(C=3C4=CC=CN=C4C=CC=3)=CN=C2NC(=O)N1C(C)C1=CC=NC=C1 BOKZGMLRHMVLAI-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 1
- UJLAXZVIDWPWRA-UHFFFAOYSA-N 3-(2,2-dimethylpropyl)-5-(2-methoxy-5-propan-2-ylphenyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound COC1=CC=C(C(C)C)C=C1C1=CN=C(NC(=O)N2CC(C)(C)C)C2=N1 UJLAXZVIDWPWRA-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 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 description 1
- HTOCMIQLIPPYMM-UHFFFAOYSA-N 3-(2-hydroxyethyl)-5-(2-methoxy-5-propan-2-ylphenyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound COC1=CC=C(C(C)C)C=C1C1=CN=C(NC(=O)N2CCO)C2=N1 HTOCMIQLIPPYMM-UHFFFAOYSA-N 0.000 description 1
- UWGGCVWPZPWUJI-UHFFFAOYSA-N 3-(2-hydroxyethyl)-5-(4-hydroxyphenyl)-1H-imidazo[4,5-b]pyrazin-2-one Chemical compound C=1N=C2NC(=O)N(CCO)C2=NC=1C1=CC=C(O)C=C1 UWGGCVWPZPWUJI-UHFFFAOYSA-N 0.000 description 1
- BMCKDBYGFGKYJJ-UHFFFAOYSA-N 3-(2-methyl-2-morpholin-4-ylpropyl)-5-[4-(1h-1,2,4-triazol-5-yl)phenyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1COCCN1C(C)(C)CN(C(NC1=NC=2)=O)C1=NC=2C(C=C1)=CC=C1C1=NN=CN1 BMCKDBYGFGKYJJ-UHFFFAOYSA-N 0.000 description 1
- BXACHSUDXJSFOJ-UHFFFAOYSA-N 3-(2-piperidin-1-ylethyl)-5-[4-(1h-1,2,4-triazol-5-yl)phenyl]-1h-imidazo[4,5-b]pyrazin-2-one;hydrochloride Chemical compound Cl.O=C1NC2=NC=C(C=3C=CC(=CC=3)C=3NC=NN=3)N=C2N1CCN1CCCCC1 BXACHSUDXJSFOJ-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 1
- XXHQSBYZXVKKML-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-(1h-indazol-5-yl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=C4C=NNC4=CC=3)N=C2N1CC1CCCCC1 XXHQSBYZXVKKML-UHFFFAOYSA-N 0.000 description 1
- QGZGXGGLQSWROG-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-(1h-indol-5-yl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=C4C=CNC4=CC=3)N=C2N1CC1CCCCC1 QGZGXGGLQSWROG-UHFFFAOYSA-N 0.000 description 1
- CVVQIXYCZOMPBT-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-(1h-indol-6-yl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=C4NC=CC4=CC=3)N=C2N1CC1CCCCC1 CVVQIXYCZOMPBT-UHFFFAOYSA-N 0.000 description 1
- CMPWOMDQTRVXFB-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-(1h-pyrazol-4-yl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C3=CNN=C3)N=C2N1CC1CCCCC1 CMPWOMDQTRVXFB-UHFFFAOYSA-N 0.000 description 1
- WLGSCAIGYWPKMK-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-(1h-pyrazol-5-yl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3NN=CC=3)N=C2N1CC1CCCCC1 WLGSCAIGYWPKMK-UHFFFAOYSA-N 0.000 description 1
- MDCNFFXUJKMFRH-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-(2-methoxy-5-propan-2-ylphenyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound COC1=CC=C(C(C)C)C=C1C1=CN=C(NC(=O)N2CC3CCCCC3)C2=N1 MDCNFFXUJKMFRH-UHFFFAOYSA-N 0.000 description 1
- BWYPXDIMFQJVTN-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-(2-methoxypyridin-4-yl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=NC(OC)=CC(C=2N=C3N(CC4CCCCC4)C(=O)NC3=NC=2)=C1 BWYPXDIMFQJVTN-UHFFFAOYSA-N 0.000 description 1
- SZUGKOACIOLZEX-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-(2-oxo-1,3-dihydroindol-5-yl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C=1C=C2NC(=O)CC2=CC=1C(N=C12)=CN=C1NC(=O)N2CC1CCCCC1 SZUGKOACIOLZEX-UHFFFAOYSA-N 0.000 description 1
- JMLNCVGLQXECPM-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-(2-oxo-1,3-dihydroindol-6-yl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=C2NC(=O)CC2=CC=C1C(N=C12)=CN=C1NC(=O)N2CC1CCCCC1 JMLNCVGLQXECPM-UHFFFAOYSA-N 0.000 description 1
- VYQWSLNATWQZNQ-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-(2-oxo-1h-pyridin-4-yl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=NC(O)=CC(C=2N=C3N(CC4CCCCC4)C(=O)NC3=NC=2)=C1 VYQWSLNATWQZNQ-UHFFFAOYSA-N 0.000 description 1
- KKNIQSPXTAJAKL-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-(4-hydroxy-2-methylphenyl)-1H-imidazo[4,5-b]pyrazin-2-one Chemical compound CC1=CC(O)=CC=C1C1=CN=C(NC(=O)N2CC3CCCCC3)C2=N1 KKNIQSPXTAJAKL-UHFFFAOYSA-N 0.000 description 1
- HHPDRWBCLDJWTP-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-(4-imidazol-1-ylphenyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=CC(=CC=3)N3C=NC=C3)N=C2N1CC1CCCCC1 HHPDRWBCLDJWTP-UHFFFAOYSA-N 0.000 description 1
- NCTXOQVCFIYCSU-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-(6-methoxypyridin-3-yl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=NC(OC)=CC=C1C1=CN=C(NC(=O)N2CC3CCCCC3)C2=N1 NCTXOQVCFIYCSU-UHFFFAOYSA-N 0.000 description 1
- HXOPCOVPPFSMFA-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-(6-oxo-1h-pyridin-3-yl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=NC(O)=CC=C1C1=CN=C(NC(=O)N2CC3CCCCC3)C2=N1 HXOPCOVPPFSMFA-UHFFFAOYSA-N 0.000 description 1
- BWFBLSMKLIDEEE-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-[2-(2-methoxyethylamino)pyrimidin-5-yl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=NC(NCCOC)=NC=C1C1=CN=C(NC(=O)N2CC3CCCCC3)C2=N1 BWFBLSMKLIDEEE-UHFFFAOYSA-N 0.000 description 1
- CGSJJFWISCGFKU-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-[2-(methylamino)pyrimidin-5-yl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=NC(NC)=NC=C1C1=CN=C(NC(=O)N2CC3CCCCC3)C2=N1 CGSJJFWISCGFKU-UHFFFAOYSA-N 0.000 description 1
- GJLLXBAFMTVTAF-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-[3-(1h-1,2,4-triazol-5-yl)phenyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=C(C=CC=3)C3=NNC=N3)N=C2N1CC1CCCCC1 GJLLXBAFMTVTAF-UHFFFAOYSA-N 0.000 description 1
- JKTKEDFHRYPXFY-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-[3-(2h-tetrazol-5-yl)phenyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=C(C=CC=3)C=3NN=NN=3)N=C2N1CC1CCCCC1 JKTKEDFHRYPXFY-UHFFFAOYSA-N 0.000 description 1
- BDYXMDOMPQWGPR-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-[3-(2h-triazol-4-yl)phenyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=C(C=CC=3)C3=NNN=C3)N=C2N1CC1CCCCC1 BDYXMDOMPQWGPR-UHFFFAOYSA-N 0.000 description 1
- FBUAMMUFCNRJOI-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-[4-(1,3-oxazol-5-yl)phenyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=CC(=CC=3)C=3OC=NC=3)N=C2N1CC1CCCCC1 FBUAMMUFCNRJOI-UHFFFAOYSA-N 0.000 description 1
- CFMIKFFITYIZAA-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-[4-(1h-1,2,4-triazol-5-yl)phenyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=CC(=CC=3)C3=NNC=N3)N=C2N1CC1CCCCC1 CFMIKFFITYIZAA-UHFFFAOYSA-N 0.000 description 1
- WOMACFLNSYTUOO-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-[4-(1h-imidazol-2-yl)phenyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=CC(=CC=3)C=3NC=CN=3)N=C2N1CC1CCCCC1 WOMACFLNSYTUOO-UHFFFAOYSA-N 0.000 description 1
- PYCNDDRHPKYGKP-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-[4-(1h-pyrazol-4-yl)phenyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=CC(=CC=3)C3=CNN=C3)N=C2N1CC1CCCCC1 PYCNDDRHPKYGKP-UHFFFAOYSA-N 0.000 description 1
- NLUSWVMGTCCSDX-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-[4-(1h-pyrazol-5-yl)phenyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=CC(=CC=3)C3=NNC=C3)N=C2N1CC1CCCCC1 NLUSWVMGTCCSDX-UHFFFAOYSA-N 0.000 description 1
- BHPWHRPVZOWBAN-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-[4-(2-hydroxypropan-2-yl)phenyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=CC(C(C)(O)C)=CC=C1C1=CN=C(NC(=O)N2CC3CCCCC3)C2=N1 BHPWHRPVZOWBAN-UHFFFAOYSA-N 0.000 description 1
- NNGMJGUIHOKDNH-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-[4-(2h-tetrazol-5-yl)phenyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=CC(=CC=3)C3=NNN=N3)N=C2N1CC1CCCCC1 NNGMJGUIHOKDNH-UHFFFAOYSA-N 0.000 description 1
- VWMRRGITEQHWJA-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-[4-(5-methyl-1h-1,2,4-triazol-3-yl)phenyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound N1C(C)=NC(C=2C=CC(=CC=2)C=2N=C3N(CC4CCCCC4)C(=O)NC3=NC=2)=N1 VWMRRGITEQHWJA-UHFFFAOYSA-N 0.000 description 1
- XERLYFQBPNSINL-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-[4-(hydroxymethyl)phenyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=CC(CO)=CC=C1C1=CN=C(NC(=O)N2CC3CCCCC3)C2=N1 XERLYFQBPNSINL-UHFFFAOYSA-N 0.000 description 1
- RQSUJEWZKKTMQG-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-[4-(triazol-1-yl)phenyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=CC(=CC=3)N3N=NC=C3)N=C2N1CC1CCCCC1 RQSUJEWZKKTMQG-UHFFFAOYSA-N 0.000 description 1
- YZDJFWPJJBQFGI-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-[4-[5-(trifluoromethyl)-1h-1,2,4-triazol-3-yl]phenyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound N1C(C(F)(F)F)=NC(C=2C=CC(=CC=2)C=2N=C3N(CC4CCCCC4)C(=O)NC3=NC=2)=N1 YZDJFWPJJBQFGI-UHFFFAOYSA-N 0.000 description 1
- DYPAWPXIWPUQON-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-phenyl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=CC=CC=3)N=C2N1CC1CCCCC1 DYPAWPXIWPUQON-UHFFFAOYSA-N 0.000 description 1
- BRPKRMNEDQAYAY-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-pyridin-2-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3N=CC=CC=3)N=C2N1CC1CCCCC1 BRPKRMNEDQAYAY-UHFFFAOYSA-N 0.000 description 1
- VLDWUBVXCBQALE-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=NC=CC=3)N=C2N1CC1CCCCC1 VLDWUBVXCBQALE-UHFFFAOYSA-N 0.000 description 1
- FUCYFCCSZXARSC-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-pyridin-4-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=CN=CC=3)N=C2N1CC1CCCCC1 FUCYFCCSZXARSC-UHFFFAOYSA-N 0.000 description 1
- RSCAAFNQCCFNMP-UHFFFAOYSA-N 3-(cyclohexylmethyl)-5-pyrimidin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=NC=NC=3)N=C2N1CC1CCCCC1 RSCAAFNQCCFNMP-UHFFFAOYSA-N 0.000 description 1
- PDADHBZGJTZQCN-UHFFFAOYSA-N 3-(cyclopentylmethyl)-5-(2-methoxy-5-propan-2-ylphenyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound COC1=CC=C(C(C)C)C=C1C1=CN=C(NC(=O)N2CC3CCCC3)C2=N1 PDADHBZGJTZQCN-UHFFFAOYSA-N 0.000 description 1
- HENVKNQFRDGZLT-UHFFFAOYSA-N 3-(cyclopentylmethyl)-5-(4-hydroxyphenyl)-1H-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=CC(O)=CC=C1C1=CN=C(NC(=O)N2CC3CCCC3)C2=N1 HENVKNQFRDGZLT-UHFFFAOYSA-N 0.000 description 1
- SDSKKSXAVZBIAN-UHFFFAOYSA-N 3-(cyclopentylmethyl)-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C4=CC=CN=C4C=CC=3)N=C2N1CC1CCCC1 SDSKKSXAVZBIAN-UHFFFAOYSA-N 0.000 description 1
- DPLBRXNWXNJZRA-UHFFFAOYSA-N 3-(cyclopropylmethyl)-5-(2-methoxy-5-propan-2-ylphenyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound COC1=CC=C(C(C)C)C=C1C1=CN=C(NC(=O)N2CC3CC3)C2=N1 DPLBRXNWXNJZRA-UHFFFAOYSA-N 0.000 description 1
- USIZAOCKUYIISW-UHFFFAOYSA-N 3-(oxan-3-yl)-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C4=CC=CN=C4C=CC=3)N=C2N1C1CCCOC1 USIZAOCKUYIISW-UHFFFAOYSA-N 0.000 description 1
- IJGOUGXLJVQAIN-UHFFFAOYSA-N 3-(oxan-4-yl)-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C4=CC=CN=C4C=CC=3)N=C2N1C1CCOCC1 IJGOUGXLJVQAIN-UHFFFAOYSA-N 0.000 description 1
- ILBAZYQADSYRJP-UHFFFAOYSA-N 3-(oxan-4-ylmethyl)-5-(1h-pyrazol-4-yl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C3=CNN=C3)N=C2N1CC1CCOCC1 ILBAZYQADSYRJP-UHFFFAOYSA-N 0.000 description 1
- UTQXEWRMPWTKGV-UHFFFAOYSA-N 3-(oxan-4-ylmethyl)-5-(3,4,5-trimethoxyphenyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3N(CC4CCOCC4)C(=O)NC3=NC=2)=C1 UTQXEWRMPWTKGV-UHFFFAOYSA-N 0.000 description 1
- UYHJRNVVRSAPDJ-UHFFFAOYSA-N 3-(oxan-4-ylmethyl)-5-(4-pyrazol-1-ylphenyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=CC(=CC=3)N3N=CC=C3)N=C2N1CC1CCOCC1 UYHJRNVVRSAPDJ-UHFFFAOYSA-N 0.000 description 1
- NHRWVYXOCMJUIS-UHFFFAOYSA-N 3-(oxan-4-ylmethyl)-5-[4-(1h-1,2,4-triazol-5-yl)phenyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=CC(=CC=3)C=3NC=NN=3)N=C2N1CC1CCOCC1 NHRWVYXOCMJUIS-UHFFFAOYSA-N 0.000 description 1
- BROBXPCIVOWKSY-UHFFFAOYSA-N 3-(oxan-4-ylmethyl)-5-[6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=NC(=CC=3)C3=NNC=N3)N=C2N1CC1CCOCC1 BROBXPCIVOWKSY-UHFFFAOYSA-N 0.000 description 1
- RPYCPMGUICEQGN-UHFFFAOYSA-N 3-(piperidin-4-ylmethyl)-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C4=CC=CN=C4C=CC=3)N=C2N1CC1CCNCC1 RPYCPMGUICEQGN-UHFFFAOYSA-N 0.000 description 1
- GXTJPCRFZLLAQY-SECBINFHSA-N 3-[(1r)-1-phenylethyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1([C@@H](C)N2C(NC3=NC=CN=C32)=O)=CC=CC=C1 GXTJPCRFZLLAQY-SECBINFHSA-N 0.000 description 1
- KHUDFKOMPUTJHV-CQSZACIVSA-N 3-[(1r)-1-phenylethyl]-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1([C@@H](C)N2C(NC3=NC=C(N=C32)C=2C3=CC=CN=C3C=CC=2)=O)=CC=CC=C1 KHUDFKOMPUTJHV-CQSZACIVSA-N 0.000 description 1
- LFUAZCRRROSASB-OAHLLOKOSA-N 3-[(1r)-1-phenylethyl]-5-quinolin-5-yl-1h-imidazo[4,5-b]pyridin-2-one Chemical compound C1([C@@H](C)N2C(NC3=CC=C(N=C32)C=2C3=CC=CN=C3C=CC=2)=O)=CC=CC=C1 LFUAZCRRROSASB-OAHLLOKOSA-N 0.000 description 1
- DIZWAEYOHSAAHB-HXUWFJFHSA-N 3-[(1r)-1-phenylpropyl]-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1([C@@H](CC)N2C(NC3=NC=C(N=C32)C=2C3=CC=CN=C3C=CC=2)=O)=CC=CC=C1 DIZWAEYOHSAAHB-HXUWFJFHSA-N 0.000 description 1
- LPHOVUYRCJSZPO-IBGZPJMESA-N 3-[(1r)-2-hydroxy-1-phenylethyl]-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1([C@H](CO)N2C(NC3=NC=C(N=C32)C=2C3=CC=CN=C3C=CC=2)=O)=CC=CC=C1 LPHOVUYRCJSZPO-IBGZPJMESA-N 0.000 description 1
- GXTJPCRFZLLAQY-VIFPVBQESA-N 3-[(1s)-1-phenylethyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1([C@H](C)N2C(NC3=NC=CN=C32)=O)=CC=CC=C1 GXTJPCRFZLLAQY-VIFPVBQESA-N 0.000 description 1
- KHUDFKOMPUTJHV-AWEZNQCLSA-N 3-[(1s)-1-phenylethyl]-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1([C@H](C)N2C(NC3=NC=C(N=C32)C=2C3=CC=CN=C3C=CC=2)=O)=CC=CC=C1 KHUDFKOMPUTJHV-AWEZNQCLSA-N 0.000 description 1
- DIZWAEYOHSAAHB-FQEVSTJZSA-N 3-[(1s)-1-phenylpropyl]-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1([C@H](CC)N2C(NC3=NC=C(N=C32)C=2C3=CC=CN=C3C=CC=2)=O)=CC=CC=C1 DIZWAEYOHSAAHB-FQEVSTJZSA-N 0.000 description 1
- LPHOVUYRCJSZPO-LJQANCHMSA-N 3-[(1s)-2-hydroxy-1-phenylethyl]-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1([C@@H](CO)N2C(NC3=NC=C(N=C32)C=2C3=CC=CN=C3C=CC=2)=O)=CC=CC=C1 LPHOVUYRCJSZPO-LJQANCHMSA-N 0.000 description 1
- TWFWQSRQIAZZLO-INIZCTEOSA-N 3-[(2r)-1-hydroxy-3-methylbutan-2-yl]-5-(2-methoxy-5-propan-2-ylphenyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound COC1=CC=C(C(C)C)C=C1C1=CN=C(NC(=O)N2[C@@H](CO)C(C)C)C2=N1 TWFWQSRQIAZZLO-INIZCTEOSA-N 0.000 description 1
- IHTQPANSAMUORS-ZDUSSCGKSA-N 3-[(2r)-1-hydroxy-3-methylbutan-2-yl]-5-phenyl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C=1N=C2NC(=O)N([C@@H](CO)C(C)C)C2=NC=1C1=CC=CC=C1 IHTQPANSAMUORS-ZDUSSCGKSA-N 0.000 description 1
- RJIVOEPSWUCCQO-INIZCTEOSA-N 3-[(2r)-1-hydroxy-3-methylbutan-2-yl]-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=CC=C2C(C=3N=C4N(C(NC4=NC=3)=O)[C@@H](CO)C(C)C)=CC=CC2=N1 RJIVOEPSWUCCQO-INIZCTEOSA-N 0.000 description 1
- TWFWQSRQIAZZLO-MRXNPFEDSA-N 3-[(2s)-1-hydroxy-3-methylbutan-2-yl]-5-(2-methoxy-5-propan-2-ylphenyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound COC1=CC=C(C(C)C)C=C1C1=CN=C(NC(=O)N2[C@H](CO)C(C)C)C2=N1 TWFWQSRQIAZZLO-MRXNPFEDSA-N 0.000 description 1
- OWGBICBGEABZQX-GOSISDBHSA-N 3-[(2s)-1-hydroxy-3-methylbutan-2-yl]-5-(2-methoxy-5-propan-2-ylphenyl)-1h-imidazo[4,5-b]pyridin-2-one Chemical compound COC1=CC=C(C(C)C)C=C1C1=CC=C(NC(=O)N2[C@H](CO)C(C)C)C2=N1 OWGBICBGEABZQX-GOSISDBHSA-N 0.000 description 1
- IHTQPANSAMUORS-CYBMUJFWSA-N 3-[(2s)-1-hydroxy-3-methylbutan-2-yl]-5-phenyl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C=1N=C2NC(=O)N([C@H](CO)C(C)C)C2=NC=1C1=CC=CC=C1 IHTQPANSAMUORS-CYBMUJFWSA-N 0.000 description 1
- RJIVOEPSWUCCQO-MRXNPFEDSA-N 3-[(2s)-1-hydroxy-3-methylbutan-2-yl]-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=CC=C2C(C=3N=C4N(C(NC4=NC=3)=O)[C@H](CO)C(C)C)=CC=CC2=N1 RJIVOEPSWUCCQO-MRXNPFEDSA-N 0.000 description 1
- ADDMRECUTDRQOF-UHFFFAOYSA-N 3-[(3-methoxyphenyl)methyl]-5-(4-methylsulfonylphenyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound COC1=CC=CC(CN2C(NC3=NC=C(N=C32)C=2C=CC(=CC=2)S(C)(=O)=O)=O)=C1 ADDMRECUTDRQOF-UHFFFAOYSA-N 0.000 description 1
- RDQFTZRINMKEJH-UHFFFAOYSA-N 3-[(3-methoxyphenyl)methyl]-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound COC1=CC=CC(CN2C(NC3=NC=C(N=C32)C=2C3=CC=CN=C3C=CC=2)=O)=C1 RDQFTZRINMKEJH-UHFFFAOYSA-N 0.000 description 1
- PECMGNBHBQZGMY-UHFFFAOYSA-N 3-[(4-methoxyphenyl)methyl]-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)NC2=NC=C(C=3C4=CC=CN=C4C=CC=3)N=C21 PECMGNBHBQZGMY-UHFFFAOYSA-N 0.000 description 1
- UNIWWTRBQQAYEN-UHFFFAOYSA-N 3-[1-(2-fluorophenyl)ethyl]-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C12=NC(C=3C4=CC=CN=C4C=CC=3)=CN=C2NC(=O)N1C(C)C1=CC=CC=C1F UNIWWTRBQQAYEN-UHFFFAOYSA-N 0.000 description 1
- ZSQGOJJYLYQHLY-UHFFFAOYSA-N 3-[1-(3-fluorophenyl)ethyl]-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C12=NC(C=3C4=CC=CN=C4C=CC=3)=CN=C2NC(=O)N1C(C)C1=CC=CC(F)=C1 ZSQGOJJYLYQHLY-UHFFFAOYSA-N 0.000 description 1
- QTHBKIPNRPDTTR-UHFFFAOYSA-N 3-[1-(3-methoxyphenyl)ethyl]-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound COC1=CC=CC(C(C)N2C(NC3=NC=C(N=C32)C=2C3=CC=CN=C3C=CC=2)=O)=C1 QTHBKIPNRPDTTR-UHFFFAOYSA-N 0.000 description 1
- CNUDCVPOVFWLOM-UHFFFAOYSA-N 3-[1-(4-chlorophenyl)ethyl]-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C12=NC(C=3C4=CC=CN=C4C=CC=3)=CN=C2NC(=O)N1C(C)C1=CC=C(Cl)C=C1 CNUDCVPOVFWLOM-UHFFFAOYSA-N 0.000 description 1
- WJRYESMMRGRJSN-UHFFFAOYSA-N 3-[1-(4-fluorophenyl)ethyl]-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C12=NC(C=3C4=CC=CN=C4C=CC=3)=CN=C2NC(=O)N1C(C)C1=CC=C(F)C=C1 WJRYESMMRGRJSN-UHFFFAOYSA-N 0.000 description 1
- FVTLLYFQCANCPM-UHFFFAOYSA-N 3-[1-(4-methoxyphenyl)ethyl]-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=CC(OC)=CC=C1C(C)N1C(=O)NC2=NC=C(C=3C4=CC=CN=C4C=CC=3)N=C21 FVTLLYFQCANCPM-UHFFFAOYSA-N 0.000 description 1
- AARQHDYJCCUDOH-UHFFFAOYSA-N 3-[1-(4-methylsulfonylphenyl)ethyl]-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C12=NC(C=3C4=CC=CN=C4C=CC=3)=CN=C2NC(=O)N1C(C)C1=CC=C(S(C)(=O)=O)C=C1 AARQHDYJCCUDOH-UHFFFAOYSA-N 0.000 description 1
- IWZKSXBUIHRIPH-UHFFFAOYSA-N 3-[2-(2,2-dimethyloxan-4-yl)ethyl]-5-(4-hydroxyphenyl)-1H-imidazo[4,5-b]pyrazin-2-one Chemical compound C1COC(C)(C)CC1CCN1C(=O)NC2=NC=C(C=3C=CC(O)=CC=3)N=C21 IWZKSXBUIHRIPH-UHFFFAOYSA-N 0.000 description 1
- OPRKTEWQXOJCMR-UHFFFAOYSA-N 3-[2-(2-oxopyrrolidin-1-yl)ethyl]-5-[4-(1h-1,2,4-triazol-5-yl)phenyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1CCCN1CCN1C(=O)NC2=NC=C(C=3C=CC(=CC=3)C3=NNC=N3)N=C21 OPRKTEWQXOJCMR-UHFFFAOYSA-N 0.000 description 1
- WAFIIPCUXMSTHV-UHFFFAOYSA-N 3-[2-(dimethylamino)ethyl]-5-(3,4,5-trimethoxyphenyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C3N(CCN(C)C)C(=O)NC3=NC=2)=C1 WAFIIPCUXMSTHV-UHFFFAOYSA-N 0.000 description 1
- FLJFLRPENIKSPA-UHFFFAOYSA-N 3-[2-(oxan-4-yl)ethyl]-5-(4-pyrrolidin-2-ylphenyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=CC(=CC=3)C3NCCC3)N=C2N1CCC1CCOCC1 FLJFLRPENIKSPA-UHFFFAOYSA-N 0.000 description 1
- KPLIWPOLIXIVDS-UHFFFAOYSA-N 3-[2-(oxan-4-yl)ethyl]-5-(4-pyrrolidin-3-ylphenyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=CC(=CC=3)C3CNCC3)N=C2N1CCC1CCOCC1 KPLIWPOLIXIVDS-UHFFFAOYSA-N 0.000 description 1
- FFGUSRSMWFYKGK-UHFFFAOYSA-N 3-[2-(oxan-4-yl)ethyl]-5-[4-(1h-1,2,4-triazol-5-yl)phenyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=CC(=CC=3)C3=NNC=N3)N=C2N1CCC1CCOCC1 FFGUSRSMWFYKGK-UHFFFAOYSA-N 0.000 description 1
- OIOIEFYEDXUNPK-UHFFFAOYSA-N 3-[2-(oxan-4-yl)ethyl]-5-[4-(5-oxopyrrolidin-2-yl)phenyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound N1C(=O)CCC1C1=CC=C(C=2N=C3N(CCC4CCOCC4)C(=O)NC3=NC=2)C=C1 OIOIEFYEDXUNPK-UHFFFAOYSA-N 0.000 description 1
- TXHWEKWQOGLTEL-UHFFFAOYSA-N 3-[2-(oxan-4-yl)ethyl]-5-[4-(5-oxopyrrolidin-3-yl)phenyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1NC(=O)CC1C1=CC=C(C=2N=C3N(CCC4CCOCC4)C(=O)NC3=NC=2)C=C1 TXHWEKWQOGLTEL-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 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 description 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 description 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 description 1
- HMKFODIYOZGFHZ-UHFFFAOYSA-N 3-[2-oxo-3-(pyridin-4-ylmethyl)-1h-imidazo[4,5-b]pyrazin-5-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2N=C3N(CC=4C=CN=CC=4)C(=O)NC3=NC=2)=C1 HMKFODIYOZGFHZ-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 1
- GGXBOWLHTYZICB-UHFFFAOYSA-N 3-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-5-[[3-(trifluoromethyl)phenyl]methyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NCC(=O)N2CC=3C=C(C=CC=3)C(F)(F)F)C2=N1 GGXBOWLHTYZICB-UHFFFAOYSA-N 0.000 description 1
- FTWKDRGLXUXFIA-UHFFFAOYSA-N 3-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-5-[[4-(trifluoromethyl)phenyl]methyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NCC(=O)N2CC=3C=CC(=CC=3)C(F)(F)F)C2=N1 FTWKDRGLXUXFIA-UHFFFAOYSA-N 0.000 description 1
- RTEGTQQTUYNWRY-UHFFFAOYSA-N 3-[6-(methylamino)pyridin-3-yl]-5-[2-(oxan-4-yl)ethyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=NC(NC)=CC=C1C1=CN=C(NCC(=O)N2CCC3CCOCC3)C2=N1 RTEGTQQTUYNWRY-UHFFFAOYSA-N 0.000 description 1
- WEVYNIUIFUYDGI-UHFFFAOYSA-N 3-[6-[4-(trifluoromethoxy)anilino]-4-pyrimidinyl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2N=CN=C(NC=3C=CC(OC(F)(F)F)=CC=3)C=2)=C1 WEVYNIUIFUYDGI-UHFFFAOYSA-N 0.000 description 1
- UZZACWMLVMJSQP-UHFFFAOYSA-N 3-[6-carbamoyl-9-(2-methoxyphenyl)-8-oxo-7h-purin-2-yl]benzoic acid Chemical compound COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C(C=CC=3)C(O)=O)N=C21 UZZACWMLVMJSQP-UHFFFAOYSA-N 0.000 description 1
- XRNYWLDXBHUCBM-UHFFFAOYSA-N 3-[7-methyl-2-(methylamino)-3h-benzimidazol-5-yl]-5-(oxan-4-ylmethyl)-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=C2NC(NC)=NC2=C(C)C=C1C(N=C12)=CN=C1NCC(=O)N2CC1CCOCC1 XRNYWLDXBHUCBM-UHFFFAOYSA-N 0.000 description 1
- AIIZSXHNWBDUIY-UHFFFAOYSA-N 3-[[3-[2-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-6-oxo-7,8-dihydropyrazino[2,3-b]pyrazin-5-yl]methyl]benzonitrile Chemical compound CC1=NC(C=2NC=NN=2)=CC=C1C(N=C12)=CN=C1NCC(=O)N2CC1=CC=CC(C#N)=C1 AIIZSXHNWBDUIY-UHFFFAOYSA-N 0.000 description 1
- KGKGEMANEQVBIB-UHFFFAOYSA-N 3-[[3-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-6-oxo-7,8-dihydropyrazino[2,3-b]pyrazin-5-yl]methyl]benzonitrile Chemical compound C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NCC(=O)N2CC=3C=C(C=CC=3)C#N)C2=N1 KGKGEMANEQVBIB-UHFFFAOYSA-N 0.000 description 1
- ZPKIIKLGZKVLEC-UHFFFAOYSA-N 3-benzhydryl-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C4=CC=CN=C4C=CC=3)N=C2N1C(C=1C=CC=CC=1)C1=CC=CC=C1 ZPKIIKLGZKVLEC-UHFFFAOYSA-N 0.000 description 1
- ZWWBXPOEHMOTPD-UHFFFAOYSA-N 3-benzyl-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C4=CC=CN=C4C=CC=3)N=C2N1CC1=CC=CC=C1 ZWWBXPOEHMOTPD-UHFFFAOYSA-N 0.000 description 1
- HOVCVDFQAJNOQH-UHFFFAOYSA-N 3-cyclohexyl-5-(2-methoxy-5-propan-2-ylphenyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound COC1=CC=C(C(C)C)C=C1C1=CN=C(NC(=O)N2C3CCCCC3)C2=N1 HOVCVDFQAJNOQH-UHFFFAOYSA-N 0.000 description 1
- PDAFTNNESCEUPA-UHFFFAOYSA-N 3-cyclopentyl-5-(2-methoxy-5-propan-2-ylphenyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound COC1=CC=C(C(C)C)C=C1C1=CN=C(NC(=O)N2C3CCCC3)C2=N1 PDAFTNNESCEUPA-UHFFFAOYSA-N 0.000 description 1
- ICFDZIRYJSCARC-UHFFFAOYSA-N 3-cyclopentyl-5-(4-hydroxyphenyl)-1H-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=CC(O)=CC=C1C1=CN=C(NC(=O)N2C3CCCC3)C2=N1 ICFDZIRYJSCARC-UHFFFAOYSA-N 0.000 description 1
- COTHFRRHLOLRAQ-UHFFFAOYSA-N 3-cyclopentyl-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C4=CC=CN=C4C=CC=3)N=C2N1C1CCCC1 COTHFRRHLOLRAQ-UHFFFAOYSA-N 0.000 description 1
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 1
- QIUBCQAHVFJLRL-UHFFFAOYSA-N 3-methyl-6-[2-methyl-4-(1h-1,2,4-triazol-5-yl)phenyl]-4-[2-(oxan-4-yl)ethyl]-1,3-dihydropyrazino[2,3-b]pyrazin-2-one Chemical compound C12=NC(C=3C(=CC(=CC=3)C=3NC=NN=3)C)=CN=C2NC(=O)C(C)N1CCC1CCOCC1 QIUBCQAHVFJLRL-UHFFFAOYSA-N 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- AGQNEMOWEJPJEC-UHFFFAOYSA-N 3-phenyl-5,7-dihydroimidazo[4,5-e][1,2,4]triazin-6-one Chemical compound N1NC2=NC(=O)N=C2N=C1C1=CC=CC=C1 AGQNEMOWEJPJEC-UHFFFAOYSA-N 0.000 description 1
- VCUQYGADRBYVIF-UHFFFAOYSA-N 3-phenyl-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C4=CC=CN=C4C=CC=3)N=C2N1C1=CC=CC=C1 VCUQYGADRBYVIF-UHFFFAOYSA-N 0.000 description 1
- MYLKYFVBOPOJNX-UHFFFAOYSA-N 3-propan-2-yl-5-(3-propan-2-ylphenyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound CC(C)C1=CC=CC(C=2N=C3N(C(C)C)C(=O)NC3=NC=2)=C1 MYLKYFVBOPOJNX-UHFFFAOYSA-N 0.000 description 1
- FNCKQRKZSWHIST-UHFFFAOYSA-N 3-propan-2-yl-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=CC=C2C(C=3N=C4N(C(NC4=NC=3)=O)C(C)C)=CC=CC2=N1 FNCKQRKZSWHIST-UHFFFAOYSA-N 0.000 description 1
- UYDXGEDUFCQCKY-UHFFFAOYSA-N 4-(2-methoxyethyl)-3,3-dimethyl-6-[2-methyl-4-(1h-1,2,4-triazol-5-yl)phenyl]-1h-pyrazino[2,3-b]pyrazin-2-one Chemical compound C=1N=C2NC(=O)C(C)(C)N(CCOC)C2=NC=1C(C(=C1)C)=CC=C1C1=NN=CN1 UYDXGEDUFCQCKY-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- NYAJAFUYXKIHES-UHFFFAOYSA-N 4-[3-(cyclohexylmethyl)-2-oxo-1h-imidazo[4,5-b]pyrazin-5-yl]-3-methylbenzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1C1=CN=C(NC(=O)N2CC3CCCCC3)C2=N1 NYAJAFUYXKIHES-UHFFFAOYSA-N 0.000 description 1
- ZAZJFMPIJWEKBY-UHFFFAOYSA-N 4-[3-(cyclohexylmethyl)-2-oxo-1h-imidazo[4,5-b]pyrazin-5-yl]-n-ethylbenzamide Chemical compound C1=CC(C(=O)NCC)=CC=C1C1=CN=C(NC(=O)N2CC3CCCCC3)C2=N1 ZAZJFMPIJWEKBY-UHFFFAOYSA-N 0.000 description 1
- UHCHHHXYTUSMOL-UHFFFAOYSA-N 4-[3-(cyclohexylmethyl)-2-oxo-1h-imidazo[4,5-b]pyrazin-5-yl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=CN=C(NC(=O)N2CC3CCCCC3)C2=N1 UHCHHHXYTUSMOL-UHFFFAOYSA-N 0.000 description 1
- VRGFVCKRPYEAQX-UHFFFAOYSA-N 4-[3-(cyclohexylmethyl)-2-oxo-1h-imidazo[4,5-b]pyrazin-5-yl]-n-propan-2-ylbenzamide Chemical compound C1=CC(C(=O)NC(C)C)=CC=C1C1=CN=C(NC(=O)N2CC3CCCCC3)C2=N1 VRGFVCKRPYEAQX-UHFFFAOYSA-N 0.000 description 1
- JQICHLGPNKWAQP-UHFFFAOYSA-N 4-[3-(cyclohexylmethyl)-2-oxo-1h-imidazo[4,5-b]pyrazin-5-yl]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=CN=C(NC(=O)N2CC3CCCCC3)C2=N1 JQICHLGPNKWAQP-UHFFFAOYSA-N 0.000 description 1
- LQYQBSQPJJZUBK-UHFFFAOYSA-N 4-[3-(cyclohexylmethyl)-2-oxo-1h-imidazo[4,5-b]pyrazin-5-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CN=C(NC(=O)N2CC3CCCCC3)C2=N1 LQYQBSQPJJZUBK-UHFFFAOYSA-N 0.000 description 1
- FMTCJUPVXLEVLA-UHFFFAOYSA-N 4-[3-(cyclohexylmethyl)-2-oxo-1h-imidazo[4,5-b]pyrazin-5-yl]benzonitrile Chemical compound O=C1NC2=NC=C(C=3C=CC(=CC=3)C#N)N=C2N1CC1CCCCC1 FMTCJUPVXLEVLA-UHFFFAOYSA-N 0.000 description 1
- RPMAINMFJQKYRB-UHFFFAOYSA-N 4-[3-[2-(oxan-4-yl)ethyl]-2-oxo-1h-imidazo[4,5-b]pyrazin-5-yl]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=CN=C(NC(=O)N2CCC3CCOCC3)C2=N1 RPMAINMFJQKYRB-UHFFFAOYSA-N 0.000 description 1
- AIKYLWPUJLUTTF-UHFFFAOYSA-N 4-[6-carbamoyl-9-(2-methoxyphenyl)-8-oxo-7h-purin-2-yl]benzoic acid Chemical compound COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=CC(=CC=3)C(O)=O)N=C21 AIKYLWPUJLUTTF-UHFFFAOYSA-N 0.000 description 1
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 1
- GHGBFKSWXMVGCZ-UHFFFAOYSA-N 4-ethyl-3,3-dimethyl-6-[2-methyl-4-(1h-1,2,4-triazol-5-yl)phenyl]-1h-pyrazino[2,3-b]pyrazin-2-one Chemical compound C=1N=C2NC(=O)C(C)(C)N(CC)C2=NC=1C(C(=C1)C)=CC=C1C1=NN=CN1 GHGBFKSWXMVGCZ-UHFFFAOYSA-N 0.000 description 1
- FBBNTTOMEWSAAE-UHFFFAOYSA-N 4-methyl-5-(6-oxo-5-propan-2-yl-7,8-dihydropyrazino[2,3-b]pyrazin-3-yl)pyridine-2-carboxamide Chemical compound N1=C2N(C(C)C)C(=O)CNC2=NC=C1C1=CN=C(C(N)=O)C=C1C FBBNTTOMEWSAAE-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- MSXKZSYIJSJAEO-UHFFFAOYSA-N 5-(1-hydroxypropan-2-yl)-3-[2-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(C(CO)C)C(=O)CNC2=NC=C1C(C(=N1)C)=CC=C1C=1N=CNN=1 MSXKZSYIJSJAEO-UHFFFAOYSA-N 0.000 description 1
- FZWCKMZSFGGKEH-UHFFFAOYSA-N 5-(1h-imidazo[4,5-b]pyridin-6-yl)-3-(oxan-4-ylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=C4N=CNC4=NC=3)N=C2N1CC1CCOCC1 FZWCKMZSFGGKEH-UHFFFAOYSA-N 0.000 description 1
- JPMOMDVUKVSFMP-UHFFFAOYSA-N 5-(1h-indol-5-yl)-3-(oxan-4-ylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=C4C=CNC4=CC=3)N=C2N1CC1CCOCC1 JPMOMDVUKVSFMP-UHFFFAOYSA-N 0.000 description 1
- MZPQLVIOWGARGY-UHFFFAOYSA-N 5-(2-amino-3h-benzimidazol-5-yl)-3-(oxan-4-ylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one;dihydrochloride Chemical compound Cl.Cl.C=1C=C2NC(N)=NC2=CC=1C(N=C12)=CN=C1NC(=O)N2CC1CCOCC1 MZPQLVIOWGARGY-UHFFFAOYSA-N 0.000 description 1
- SYIJRJBXBTYBEZ-UHFFFAOYSA-N 5-(2-fluorophenyl)-3-(1-phenylethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C12=NC(C=3C(=CC=CC=3)F)=CN=C2NC(=O)N1C(C)C1=CC=CC=C1 SYIJRJBXBTYBEZ-UHFFFAOYSA-N 0.000 description 1
- FTQZASSPTVRUKQ-UHFFFAOYSA-N 5-(2-hydroxyethyl)-3-[2-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C=1C=C(C=2N=C3N(CCO)C(=O)CNC3=NC=2)C(C)=NC=1C=1N=CNN=1 FTQZASSPTVRUKQ-UHFFFAOYSA-N 0.000 description 1
- LJGJRIKXZVCGDN-UHFFFAOYSA-N 5-(2-methoxy-5-propan-2-ylphenyl)-3-(2-methylpropyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound COC1=CC=C(C(C)C)C=C1C1=CN=C(NC(=O)N2CC(C)C)C2=N1 LJGJRIKXZVCGDN-UHFFFAOYSA-N 0.000 description 1
- QIFAYNJRYMIRJN-UHFFFAOYSA-N 5-(2-methoxy-5-propan-2-ylphenyl)-3-(oxan-3-yl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound COC1=CC=C(C(C)C)C=C1C1=CN=C(NC(=O)N2C3COCCC3)C2=N1 QIFAYNJRYMIRJN-UHFFFAOYSA-N 0.000 description 1
- MQMVOXVEDSUHQI-UHFFFAOYSA-N 5-(2-methoxy-5-propan-2-ylphenyl)-3-(oxan-4-yl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound COC1=CC=C(C(C)C)C=C1C1=CN=C(NC(=O)N2C3CCOCC3)C2=N1 MQMVOXVEDSUHQI-UHFFFAOYSA-N 0.000 description 1
- KESYHKLQEITDQJ-CYBMUJFWSA-N 5-(2-methoxy-5-propan-2-ylphenyl)-3-[(2r)-3-methylbutan-2-yl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound COC1=CC=C(C(C)C)C=C1C1=CN=C(NC(=O)N2[C@H](C)C(C)C)C2=N1 KESYHKLQEITDQJ-CYBMUJFWSA-N 0.000 description 1
- KESYHKLQEITDQJ-ZDUSSCGKSA-N 5-(2-methoxy-5-propan-2-ylphenyl)-3-[(2s)-3-methylbutan-2-yl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound COC1=CC=C(C(C)C)C=C1C1=CN=C(NC(=O)N2[C@@H](C)C(C)C)C2=N1 KESYHKLQEITDQJ-ZDUSSCGKSA-N 0.000 description 1
- JLQWEBMTAPURRM-CYBMUJFWSA-N 5-(2-methoxy-5-propan-2-ylphenyl)-3-[(3r)-oxolan-3-yl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound COC1=CC=C(C(C)C)C=C1C1=CN=C(NC(=O)N2[C@H]3COCC3)C2=N1 JLQWEBMTAPURRM-CYBMUJFWSA-N 0.000 description 1
- JLQWEBMTAPURRM-ZDUSSCGKSA-N 5-(2-methoxy-5-propan-2-ylphenyl)-3-[(3s)-oxolan-3-yl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound COC1=CC=C(C(C)C)C=C1C1=CN=C(NC(=O)N2[C@@H]3COCC3)C2=N1 JLQWEBMTAPURRM-ZDUSSCGKSA-N 0.000 description 1
- OMPIISLASYMVQK-UHFFFAOYSA-N 5-(2-methoxy-5-propan-2-ylphenyl)-3-propan-2-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound COC1=CC=C(C(C)C)C=C1C1=CN=C(NC(=O)N2C(C)C)C2=N1 OMPIISLASYMVQK-UHFFFAOYSA-N 0.000 description 1
- NVSABGFUPYOXBC-UHFFFAOYSA-N 5-(2-methoxyethyl)-3-[2-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CCOC)C(=O)CNC2=NC=C1C(C(=N1)C)=CC=C1C1=NN=CN1 NVSABGFUPYOXBC-UHFFFAOYSA-N 0.000 description 1
- NFQHGHLEMBPSNM-UHFFFAOYSA-N 5-(2-methoxyethyl)-3-[4-(1h-pyrazol-5-yl)phenyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CCOC)C(=O)CNC2=NC=C1C(C=C1)=CC=C1C=1C=CNN=1 NFQHGHLEMBPSNM-UHFFFAOYSA-N 0.000 description 1
- NUJKYWRSJNHBNP-UHFFFAOYSA-N 5-(2-methoxyethyl)-3-[4-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CCOC)C(=O)CNC2=NC=C1C(C(=C1)C)=CN=C1C=1N=CNN=1 NUJKYWRSJNHBNP-UHFFFAOYSA-N 0.000 description 1
- ZPSNIJRHIXWNJC-UHFFFAOYSA-N 5-(2-methoxyethyl)-3-[6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CCOC)C(=O)CNC2=NC=C1C(C=N1)=CC=C1C=1N=CNN=1 ZPSNIJRHIXWNJC-UHFFFAOYSA-N 0.000 description 1
- INRMHRKIRHNHFX-UHFFFAOYSA-N 5-(2-methoxyethyl)-3-[7-methyl-2-(methylamino)-3h-benzimidazol-5-yl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1CC(=O)N(CCOC)C2=NC(C3=CC(C)=C4N=C(NC4=C3)NC)=CN=C21 INRMHRKIRHNHFX-UHFFFAOYSA-N 0.000 description 1
- FSPTUMMDZLMOBH-UHFFFAOYSA-N 5-(2-methoxyphenyl)-3-propan-2-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound COC1=CC=CC=C1C1=CN=C(NC(=O)N2C(C)C)C2=N1 FSPTUMMDZLMOBH-UHFFFAOYSA-N 0.000 description 1
- JIXAPXSEURQWSR-UHFFFAOYSA-N 5-(2-methyl-3h-benzimidazol-5-yl)-3-(oxan-4-ylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one;hydrochloride Chemical compound Cl.C=1C=C2NC(C)=NC2=CC=1C(N=C12)=CN=C1NC(=O)N2CC1CCOCC1 JIXAPXSEURQWSR-UHFFFAOYSA-N 0.000 description 1
- UJKVMWYLCRUHPM-UHFFFAOYSA-N 5-(3-aminophenyl)-3-(1-phenylethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C12=NC(C=3C=C(N)C=CC=3)=CN=C2NC(=O)N1C(C)C1=CC=CC=C1 UJKVMWYLCRUHPM-UHFFFAOYSA-N 0.000 description 1
- PWWWAFNIOCQDNC-UHFFFAOYSA-N 5-(3-fluorophenyl)-3-(1-phenylethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C12=NC(C=3C=C(F)C=CC=3)=CN=C2NC(=O)N1C(C)C1=CC=CC=C1 PWWWAFNIOCQDNC-UHFFFAOYSA-N 0.000 description 1
- SXFSVQGLVPFKRK-UHFFFAOYSA-N 5-(3-hydroxyphenyl)-3-(2-methoxyphenyl)-1h-imidazo[4,5-b]pyridin-2-one Chemical compound COC1=CC=CC=C1N1C(=O)NC2=CC=C(C=3C=C(O)C=CC=3)N=C21 SXFSVQGLVPFKRK-UHFFFAOYSA-N 0.000 description 1
- ILSXODFJMXMIPP-UHFFFAOYSA-N 5-(3-methylsulfonylphenyl)-3-(1-phenylethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C12=NC(C=3C=C(C=CC=3)S(C)(=O)=O)=CN=C2NC(=O)N1C(C)C1=CC=CC=C1 ILSXODFJMXMIPP-UHFFFAOYSA-N 0.000 description 1
- ARAFZLNEXXVYMQ-UHFFFAOYSA-N 5-(3h-benzimidazol-5-yl)-3-(cyclohexylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=C4N=CNC4=CC=3)N=C2N1CC1CCCCC1 ARAFZLNEXXVYMQ-UHFFFAOYSA-N 0.000 description 1
- JZKBZHHHTWFSEL-UHFFFAOYSA-N 5-(4-hydroxyphenyl)-3-(2-morpholin-4-ylethyl)-1H-imidazo[4,5-b]pyrazin-2-one hydrochloride Chemical compound Cl.C1=CC(O)=CC=C1C1=CN=C(NC(=O)N2CCN3CCOCC3)C2=N1 JZKBZHHHTWFSEL-UHFFFAOYSA-N 0.000 description 1
- RYQIOZIGGZLCGI-UHFFFAOYSA-N 5-(4-hydroxyphenyl)-3-(3-methoxypropyl)-1H-imidazo[4,5-b]pyrazin-2-one Chemical compound C=1N=C2NC(=O)N(CCCOC)C2=NC=1C1=CC=C(O)C=C1 RYQIOZIGGZLCGI-UHFFFAOYSA-N 0.000 description 1
- AYLGJAHVVVLNQM-UHFFFAOYSA-N 5-(4-hydroxyphenyl)-3-(oxan-3-ylmethyl)-1H-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=CC(O)=CC=C1C1=CN=C(NC(=O)N2CC3COCCC3)C2=N1 AYLGJAHVVVLNQM-UHFFFAOYSA-N 0.000 description 1
- CCIYOKFLOBWGJQ-UHFFFAOYSA-N 5-(4-hydroxyphenyl)-3-(oxolan-2-ylmethyl)-1H-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=CC(O)=CC=C1C1=CN=C(NC(=O)N2CC3OCCC3)C2=N1 CCIYOKFLOBWGJQ-UHFFFAOYSA-N 0.000 description 1
- ANBMVHOESRWVJC-UHFFFAOYSA-N 5-(4-hydroxyphenyl)-3-(oxolan-3-ylmethyl)-1H-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=CC(O)=CC=C1C1=CN=C(NC(=O)N2CC3COCC3)C2=N1 ANBMVHOESRWVJC-UHFFFAOYSA-N 0.000 description 1
- PCEXVGQHWNHDQF-UHFFFAOYSA-N 5-(4-hydroxyphenyl)-3-(piperidin-3-ylmethyl)-1H-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=CC(O)=CC=C1C1=CN=C(NC(=O)N2CC3CNCCC3)C2=N1 PCEXVGQHWNHDQF-UHFFFAOYSA-N 0.000 description 1
- OZUOHCRZQNREBX-UHFFFAOYSA-N 5-(4-hydroxyphenyl)-3-(piperidin-4-ylmethyl)-1H-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=CC(O)=CC=C1C1=CN=C(NC(=O)N2CC3CCNCC3)C2=N1 OZUOHCRZQNREBX-UHFFFAOYSA-N 0.000 description 1
- YUAGNXNKUXHFTR-UHFFFAOYSA-N 5-(4-hydroxyphenyl)-3-(pyrrolidin-2-ylmethyl)-1H-imidazo[4,5-b]pyrazin-2-one hydrochloride Chemical compound Cl.C1=CC(O)=CC=C1C1=CN=C(NC(=O)N2CC3NCCC3)C2=N1 YUAGNXNKUXHFTR-UHFFFAOYSA-N 0.000 description 1
- AYQNJVRBVRIMCX-UHFFFAOYSA-N 5-(4-hydroxyphenyl)-3-[(1-methylpiperidin-2-yl)methyl]-1H-imidazo[4,5-b]pyrazin-2-one hydrochloride Chemical compound Cl.CN1CCCCC1CN1C(=O)NC2=NC=C(C=3C=CC(O)=CC=3)N=C21 AYQNJVRBVRIMCX-UHFFFAOYSA-N 0.000 description 1
- UWQROPYNVNJYIY-UHFFFAOYSA-N 5-(4-hydroxyphenyl)-3-[(1-methylpiperidin-3-yl)methyl]-1H-imidazo[4,5-b]pyrazin-2-one Chemical compound C1N(C)CCCC1CN1C(=O)NC2=NC=C(C=3C=CC(O)=CC=3)N=C21 UWQROPYNVNJYIY-UHFFFAOYSA-N 0.000 description 1
- NRWLHIDMPLEBJR-UHFFFAOYSA-N 5-(4-hydroxyphenyl)-3-[(5-oxopyrrolidin-2-yl)methyl]-1H-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=CC(O)=CC=C1C1=CN=C(NC(=O)N2CC3NC(=O)CC3)C2=N1 NRWLHIDMPLEBJR-UHFFFAOYSA-N 0.000 description 1
- SVABQAKNYVESNJ-UHFFFAOYSA-N 5-(4-hydroxyphenyl)-3-[2-(oxan-4-yl)ethyl]-1H-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=CC(O)=CC=C1C1=CN=C(NC(=O)N2CCC3CCOCC3)C2=N1 SVABQAKNYVESNJ-UHFFFAOYSA-N 0.000 description 1
- RLWYZEUPRNRMHI-UHFFFAOYSA-N 5-(4-hydroxyphenyl)-3-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=CC(O)=CC=C1C1=CN=C(NC(=O)N2CCCN3C(CCC3)=O)C2=N1 RLWYZEUPRNRMHI-UHFFFAOYSA-N 0.000 description 1
- KMLAVKBRMYAFKM-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-3-(1-phenylethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C12=NC(C=3C=CC(=CC=3)S(C)(=O)=O)=CN=C2NC(=O)N1C(C)C1=CC=CC=C1 KMLAVKBRMYAFKM-UHFFFAOYSA-N 0.000 description 1
- POKQVDAKDKKZFZ-UHFFFAOYSA-N 5-(6-aminopyridin-3-yl)-3-(oxan-4-ylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=NC(N)=CC=C1C1=CN=C(NC(=O)N2CC3CCOCC3)C2=N1 POKQVDAKDKKZFZ-UHFFFAOYSA-N 0.000 description 1
- CWIXLTRPVKXNRI-UHFFFAOYSA-N 5-(6-fluoropyridin-3-yl)-3-(oxan-4-ylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=NC(F)=CC=C1C1=CN=C(NC(=O)N2CC3CCOCC3)C2=N1 CWIXLTRPVKXNRI-UHFFFAOYSA-N 0.000 description 1
- JZXXYQZWXCXZJY-CHWSQXEVSA-N 5-[(1r,3r)-3-methoxycyclopentyl]-3-[2-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-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=3NC=NN=3)C)=CN=C2NCC1=O JZXXYQZWXCXZJY-CHWSQXEVSA-N 0.000 description 1
- JZXXYQZWXCXZJY-OLZOCXBDSA-N 5-[(1r,3s)-3-methoxycyclopentyl]-3-[2-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-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=3NC=NN=3)C)=CN=C2NCC1=O JZXXYQZWXCXZJY-OLZOCXBDSA-N 0.000 description 1
- JZXXYQZWXCXZJY-QWHCGFSZSA-N 5-[(1s,3r)-3-methoxycyclopentyl]-3-[2-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-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=3NC=NN=3)C)=CN=C2NCC1=O JZXXYQZWXCXZJY-QWHCGFSZSA-N 0.000 description 1
- JZXXYQZWXCXZJY-STQMWFEESA-N 5-[(1s,3s)-3-methoxycyclopentyl]-3-[2-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-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=3NC=NN=3)C)=CN=C2NCC1=O JZXXYQZWXCXZJY-STQMWFEESA-N 0.000 description 1
- SUDJJCJRFLFLDF-UHFFFAOYSA-N 5-[2-(dimethylamino)-3h-benzimidazol-5-yl]-3-(oxan-4-ylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C=1C=C2NC(N(C)C)=NC2=CC=1C(N=C12)=CN=C1NC(=O)N2CC1CCOCC1 SUDJJCJRFLFLDF-UHFFFAOYSA-N 0.000 description 1
- RGGDWENTCRAFSY-UHFFFAOYSA-N 5-[2-(oxan-4-yl)ethyl]-3-(1h-pyrazol-4-yl)-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound O=C1CNC2=NC=C(C3=CNN=C3)N=C2N1CCC1CCOCC1 RGGDWENTCRAFSY-UHFFFAOYSA-N 0.000 description 1
- YKVLWVMMPGATFA-UHFFFAOYSA-N 5-[2-(oxan-4-yl)ethyl]-3-(1h-pyrrolo[2,3-b]pyridin-3-yl)-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound O=C1CNC2=NC=C(C=3C4=CC=CN=C4NC=3)N=C2N1CCC1CCOCC1 YKVLWVMMPGATFA-UHFFFAOYSA-N 0.000 description 1
- SPLZOLLOHZXLCV-UHFFFAOYSA-N 5-[2-(oxan-4-yl)ethyl]-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound O=C1CNC2=NC=C(C=3C=4C=CNC=4N=CC=3)N=C2N1CCC1CCOCC1 SPLZOLLOHZXLCV-UHFFFAOYSA-N 0.000 description 1
- XLONNVXPSUTRBD-UHFFFAOYSA-N 5-[2-(oxan-4-yl)ethyl]-3-(1h-pyrrolo[2,3-b]pyridin-5-yl)-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound O=C1CNC2=NC=C(C=3C=C4C=CNC4=NC=3)N=C2N1CCC1CCOCC1 XLONNVXPSUTRBD-UHFFFAOYSA-N 0.000 description 1
- OURMEBMAEXJYKX-UHFFFAOYSA-N 5-[2-(oxan-4-yl)ethyl]-3-(2-oxo-1h-pyridin-4-yl)-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=NC(O)=CC(C=2N=C3N(CCC4CCOCC4)C(=O)CNC3=NC=2)=C1 OURMEBMAEXJYKX-UHFFFAOYSA-N 0.000 description 1
- FRJAQAFSPPSOKO-UHFFFAOYSA-N 5-[2-(oxan-4-yl)ethyl]-3-(6-oxo-1h-pyridin-3-yl)-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=NC(O)=CC=C1C1=CN=C(NCC(=O)N2CCC3CCOCC3)C2=N1 FRJAQAFSPPSOKO-UHFFFAOYSA-N 0.000 description 1
- MRVNZUNWYGONNW-UHFFFAOYSA-N 5-[2-(oxan-4-yl)ethyl]-3-[4-(1h-1,2,4-triazol-5-yl)phenyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound O=C1CNC2=NC=C(C=3C=CC(=CC=3)C=3NN=CN=3)N=C2N1CCC1CCOCC1 MRVNZUNWYGONNW-UHFFFAOYSA-N 0.000 description 1
- VRFQFZUAZKJJNU-UHFFFAOYSA-N 5-[2-(oxan-4-yl)ethyl]-3-pyridin-3-yl-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound O=C1CNC2=NC=C(C=3C=NC=CC=3)N=C2N1CCC1CCOCC1 VRFQFZUAZKJJNU-UHFFFAOYSA-N 0.000 description 1
- MGQSNZBPSZSJIQ-UHFFFAOYSA-N 5-[2-(oxan-4-yl)ethyl]-3-pyridin-4-yl-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound O=C1CNC2=NC=C(C=3C=CN=CC=3)N=C2N1CCC1CCOCC1 MGQSNZBPSZSJIQ-UHFFFAOYSA-N 0.000 description 1
- HKGGGINKRDOBEB-UHFFFAOYSA-N 5-[2-methyl-4-(1h-1,2,4-triazol-5-yl)phenyl]-3-[2-(oxan-4-yl)ethyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound CC1=CC(C2=NNC=N2)=CC=C1C(N=C12)=CN=C1NC(=O)N2CCC1CCOCC1 HKGGGINKRDOBEB-UHFFFAOYSA-N 0.000 description 1
- SYPJBUDABPWWFC-UHFFFAOYSA-N 5-[3-(dimethylamino)phenyl]-3-(1-phenylethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C12=NC(C=3C=C(C=CC=3)N(C)C)=CN=C2NC(=O)N1C(C)C1=CC=CC=C1 SYPJBUDABPWWFC-UHFFFAOYSA-N 0.000 description 1
- FJICUYATBKVLIM-UHFFFAOYSA-N 5-[3-(hydroxymethyl)thiophen-2-yl]-3-(oxan-4-ylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=CSC(C=2N=C3N(CC4CCOCC4)C(=O)NC3=NC=2)=C1CO FJICUYATBKVLIM-UHFFFAOYSA-N 0.000 description 1
- DXLPGBVBSDHEMM-UHFFFAOYSA-N 5-[4-(1h-benzimidazol-2-yl)phenyl]-3-(oxan-4-ylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=CC(=CC=3)C=3NC4=CC=CC=C4N=3)N=C2N1CC1CCOCC1 DXLPGBVBSDHEMM-UHFFFAOYSA-N 0.000 description 1
- SDOHYCHQUHBZND-UHFFFAOYSA-N 5-[4-(1h-imidazol-2-yl)phenyl]-3-(oxan-4-ylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one;hydrochloride Chemical compound Cl.O=C1NC2=NC=C(C=3C=CC(=CC=3)C=3NC=CN=3)N=C2N1CC1CCOCC1 SDOHYCHQUHBZND-UHFFFAOYSA-N 0.000 description 1
- OWRKLIBQVXFYJC-UHFFFAOYSA-N 5-[4-(1h-imidazol-5-yl)phenyl]-3-(oxan-4-ylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one;hydrochloride Chemical compound Cl.O=C1NC2=NC=C(C=3C=CC(=CC=3)C=3NC=NC=3)N=C2N1CC1CCOCC1 OWRKLIBQVXFYJC-UHFFFAOYSA-N 0.000 description 1
- IIMPGCAGKKFHHU-UHFFFAOYSA-N 5-[4-(2-hydroxypropan-2-yl)phenyl]-3-(oxan-4-ylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=CC(C(C)(O)C)=CC=C1C1=CN=C(NC(=O)N2CC3CCOCC3)C2=N1 IIMPGCAGKKFHHU-UHFFFAOYSA-N 0.000 description 1
- LWMCMSODYURSSU-UHFFFAOYSA-N 5-[4-(2-hydroxypropan-2-yl)phenyl]-3-[2-(oxan-4-yl)ethyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=CC(C(C)(O)C)=CC=C1C1=CN=C(NC(=O)N2CCC3CCOCC3)C2=N1 LWMCMSODYURSSU-UHFFFAOYSA-N 0.000 description 1
- RXGMTZODXXTWTD-UHFFFAOYSA-N 5-[4-(4,5-dimethyl-1h-imidazol-2-yl)phenyl]-3-(2-morpholin-4-ylethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound N1C(C)=C(C)N=C1C1=CC=C(C=2N=C3N(CCN4CCOCC4)C(=O)NC3=NC=2)C=C1 RXGMTZODXXTWTD-UHFFFAOYSA-N 0.000 description 1
- FDOGTFDCNZSVTD-UHFFFAOYSA-N 5-[4-(4,5-dimethyl-1h-imidazol-2-yl)phenyl]-3-(oxan-4-ylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound N1C(C)=C(C)N=C1C1=CC=C(C=2N=C3N(CC4CCOCC4)C(=O)NC3=NC=2)C=C1 FDOGTFDCNZSVTD-UHFFFAOYSA-N 0.000 description 1
- NHZWXPJUJBIXRA-UHFFFAOYSA-N 5-[4-(5-methyl-1h-1,2,4-triazol-3-yl)phenyl]-3-(2-morpholin-4-ylethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound N1C(C)=NC(C=2C=CC(=CC=2)C=2N=C3N(CCN4CCOCC4)C(=O)NC3=NC=2)=N1 NHZWXPJUJBIXRA-UHFFFAOYSA-N 0.000 description 1
- HBRKFNWZRWRDJR-UHFFFAOYSA-N 5-[4-(5-methyl-1h-1,2,4-triazol-3-yl)phenyl]-3-[2-(2-oxopyrrolidin-1-yl)ethyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound N1C(C)=NC(C=2C=CC(=CC=2)C=2N=C3N(CCN4C(CCC4)=O)C(=O)NC3=NC=2)=N1 HBRKFNWZRWRDJR-UHFFFAOYSA-N 0.000 description 1
- GSTUHFZAOYZORN-UHFFFAOYSA-N 5-[4-(5-methyl-1h-imidazol-2-yl)phenyl]-3-(oxan-4-ylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound N1C(C)=CN=C1C1=CC=C(C=2N=C3N(CC4CCOCC4)C(=O)NC3=NC=2)C=C1 GSTUHFZAOYZORN-UHFFFAOYSA-N 0.000 description 1
- UMRHEAFJGPOZGL-UHFFFAOYSA-N 5-[4-(aminomethyl)phenyl]-3-(cyclohexylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=CC(CN)=CC=C1C1=CN=C(NC(=O)N2CC3CCCCC3)C2=N1 UMRHEAFJGPOZGL-UHFFFAOYSA-N 0.000 description 1
- ABIYZEMGQIMMFY-UHFFFAOYSA-N 5-[4-(hydroxymethyl)thiophen-2-yl]-3-(oxan-4-ylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound OCC1=CSC(C=2N=C3N(CC4CCOCC4)C(=O)NC3=NC=2)=C1 ABIYZEMGQIMMFY-UHFFFAOYSA-N 0.000 description 1
- KGPWZRDBBWIJEV-UHFFFAOYSA-N 5-[4-[5-(2-hydroxypropan-2-yl)-1h-1,2,4-triazol-3-yl]phenyl]-3-(oxan-4-ylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound N1C(C(C)(O)C)=NC(C=2C=CC(=CC=2)C=2N=C3N(CC4CCOCC4)C(=O)NC3=NC=2)=N1 KGPWZRDBBWIJEV-UHFFFAOYSA-N 0.000 description 1
- QNVNKNMDTJDSKG-UHFFFAOYSA-N 5-[4-[5-(aminomethyl)-1h-1,2,4-triazol-3-yl]phenyl]-3-(cyclohexylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one;hydrochloride Chemical compound Cl.N1C(CN)=NC(C=2C=CC(=CC=2)C=2N=C3N(CC4CCCCC4)C(=O)NC3=NC=2)=N1 QNVNKNMDTJDSKG-UHFFFAOYSA-N 0.000 description 1
- ZLALIOFJRPWMTM-UHFFFAOYSA-N 5-[4-[5-(hydroxymethyl)-1h-1,2,4-triazol-3-yl]phenyl]-3-(oxan-4-ylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound N1C(CO)=NC(C=2C=CC(=CC=2)C=2N=C3N(CC4CCOCC4)C(=O)NC3=NC=2)=N1 ZLALIOFJRPWMTM-UHFFFAOYSA-N 0.000 description 1
- AADJANFGUOIFGV-UHFFFAOYSA-N 5-[4-[5-(methoxymethyl)-1h-1,2,4-triazol-3-yl]phenyl]-3-(oxan-4-ylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound N1C(COC)=NC(C=2C=CC(=CC=2)C=2N=C3N(CC4CCOCC4)C(=O)NC3=NC=2)=N1 AADJANFGUOIFGV-UHFFFAOYSA-N 0.000 description 1
- ZIFHJWSXCVZLDX-UHFFFAOYSA-N 5-[4-[5-(methylaminomethyl)-1h-1,2,4-triazol-3-yl]phenyl]-3-(oxan-4-ylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound N1C(CNC)=NC(C=2C=CC(=CC=2)C=2N=C3N(CC4CCOCC4)C(=O)NC3=NC=2)=N1 ZIFHJWSXCVZLDX-UHFFFAOYSA-N 0.000 description 1
- ZHYZCNVSJGVOPC-UHFFFAOYSA-N 5-[4-[5-(morpholin-4-ylmethyl)-1h-1,2,4-triazol-3-yl]phenyl]-3-(oxan-4-ylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound O=C1NC2=NC=C(C=3C=CC(=CC=3)C=3N=C(CN4CCOCC4)NN=3)N=C2N1CC1CCOCC1 ZHYZCNVSJGVOPC-UHFFFAOYSA-N 0.000 description 1
- CJCHYUPQYXHQLL-UHFFFAOYSA-N 5-[4-[5-[(dimethylamino)methyl]-1h-1,2,4-triazol-3-yl]phenyl]-3-(oxan-4-ylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound N1C(CN(C)C)=NC(C=2C=CC(=CC=2)C=2N=C3N(CC4CCOCC4)C(=O)NC3=NC=2)=N1 CJCHYUPQYXHQLL-UHFFFAOYSA-N 0.000 description 1
- SZMOTAFHAMLZDP-UHFFFAOYSA-N 5-[5-(2-hydroxyethyl)thiophen-2-yl]-3-(oxan-4-ylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound S1C(CCO)=CC=C1C1=CN=C(NC(=O)N2CC3CCOCC3)C2=N1 SZMOTAFHAMLZDP-UHFFFAOYSA-N 0.000 description 1
- PLWDQSKPAOOXAW-UHFFFAOYSA-N 5-[5-(hydroxymethyl)thiophen-2-yl]-3-(oxan-4-ylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound S1C(CO)=CC=C1C1=CN=C(NC(=O)N2CC3CCOCC3)C2=N1 PLWDQSKPAOOXAW-UHFFFAOYSA-N 0.000 description 1
- FPOJUEVZPINGBY-UHFFFAOYSA-N 5-[6-(methylamino)pyridin-3-yl]-3-(oxan-4-ylmethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1=NC(NC)=CC=C1C1=CN=C(NC(=O)N2CC3CCOCC3)C2=N1 FPOJUEVZPINGBY-UHFFFAOYSA-N 0.000 description 1
- WYOUELOPRDHRFN-UHFFFAOYSA-N 5-[8-(2-methoxyethyl)-6-oxo-5,7-dihydropyrazino[2,3-b]pyrazin-2-yl]-4-methylpyridine-2-carboxamide Chemical compound N1=C2N(CCOC)CC(=O)NC2=NC=C1C1=CN=C(C(N)=O)C=C1C WYOUELOPRDHRFN-UHFFFAOYSA-N 0.000 description 1
- VXXIEBRDQDDWJJ-UHFFFAOYSA-N 5-benzyl-3-[2-methyl-4-(1h-1,2,4-triazol-5-yl)phenyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound CC1=CC(C=2NC=NN=2)=CC=C1C(N=C12)=CN=C1NCC(=O)N2CC1=CC=CC=C1 VXXIEBRDQDDWJJ-UHFFFAOYSA-N 0.000 description 1
- WYLXUTPYMYKVJF-UHFFFAOYSA-N 5-ethyl-3-(1h-indazol-4-yl)-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CC)C(=O)CNC2=NC=C1C1=CC=CC2=C1C=NN2 WYLXUTPYMYKVJF-UHFFFAOYSA-N 0.000 description 1
- GZPJUEHGNHAVKF-UHFFFAOYSA-N 5-ethyl-3-(1h-pyrrolo[2,3-b]pyridin-5-yl)-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2NC=CC2=CC(C2=CN=C3NCC(=O)N(C3=N2)CC)=C1 GZPJUEHGNHAVKF-UHFFFAOYSA-N 0.000 description 1
- UYCWOEZHBUCWAC-UHFFFAOYSA-N 5-ethyl-3-(1h-pyrrolo[3,2-b]pyridin-5-yl)-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1=C2NC=CC2=NC(C2=CN=C3NCC(=O)N(C3=N2)CC)=C1 UYCWOEZHBUCWAC-UHFFFAOYSA-N 0.000 description 1
- GMYLVKUGJMYTFB-UHFFFAOYSA-N 5-ethyl-3-[2-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CC)C(=O)CNC2=NC=C1C(C(=N1)C)=CC=C1C1=NN=CN1 GMYLVKUGJMYTFB-UHFFFAOYSA-N 0.000 description 1
- ZZQICLYBVODNQP-UHFFFAOYSA-N 5-ethyl-3-[5-fluoro-2-methyl-4-(1h-1,2,4-triazol-5-yl)phenyl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CC)C(=O)CNC2=NC=C1C(C(=C1)C)=CC(F)=C1C=1N=CNN=1 ZZQICLYBVODNQP-UHFFFAOYSA-N 0.000 description 1
- UAIVVAVQNKLODW-UHFFFAOYSA-N 5-ethyl-3-[6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CC)C(=O)CNC2=NC=C1C(C=N1)=CC=C1C=1N=CNN=1 UAIVVAVQNKLODW-UHFFFAOYSA-N 0.000 description 1
- XEPYGEAUHALMSW-UHFFFAOYSA-N 5-isoquinolin-5-yl-3-(1-phenylethyl)-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C12=NC(C=3C4=CC=NC=C4C=CC=3)=CN=C2NC(=O)N1C(C)C1=CC=CC=C1 XEPYGEAUHALMSW-UHFFFAOYSA-N 0.000 description 1
- YYVCGFXRDDLIIQ-UHFFFAOYSA-N 5-methyl-3-[2-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(C)C(=O)CNC2=NC=C1C(C(=N1)C)=CC=C1C1=NN=CN1 YYVCGFXRDDLIIQ-UHFFFAOYSA-N 0.000 description 1
- GADSZCNZUXIWAA-OAHLLOKOSA-N 5-naphthalen-1-yl-3-[(1r)-1-phenylethyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1([C@@H](C)N2C(NC3=NC=C(N=C32)C=2C3=CC=CC=C3C=CC=2)=O)=CC=CC=C1 GADSZCNZUXIWAA-OAHLLOKOSA-N 0.000 description 1
- GADSZCNZUXIWAA-HNNXBMFYSA-N 5-naphthalen-1-yl-3-[(1s)-1-phenylethyl]-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1([C@H](C)N2C(NC3=NC=C(N=C32)C=2C3=CC=CC=C3C=CC=2)=O)=CC=CC=C1 GADSZCNZUXIWAA-HNNXBMFYSA-N 0.000 description 1
- DQWKXJYJKDPLMT-UHFFFAOYSA-N 5-phenoxy-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound N1=C2NC(=O)NC2=CC=C1OC1=CC=CC=C1 DQWKXJYJKDPLMT-UHFFFAOYSA-N 0.000 description 1
- HMOJZFVMIKFVAQ-UHFFFAOYSA-N 5-phenyl-1,3-dihydroimidazo[4,5-b]pyrazin-2-one Chemical compound N1=C2NC(=O)NC2=NC=C1C1=CC=CC=C1 HMOJZFVMIKFVAQ-UHFFFAOYSA-N 0.000 description 1
- RPVUSNPGWPFBMC-UHFFFAOYSA-N 5-propan-2-yl-3-[6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(C(C)C)C(=O)CNC2=NC=C1C(C=N1)=CC=C1C=1N=CNN=1 RPVUSNPGWPFBMC-UHFFFAOYSA-N 0.000 description 1
- PIZRDBDKCZOJFX-UHFFFAOYSA-N 5-quinolin-5-yl-1,3-dihydroimidazo[4,5-b]pyrazin-2-one Chemical compound C1=CC=C2C(C3=CN=C4NC(NC4=N3)=O)=CC=CC2=N1 PIZRDBDKCZOJFX-UHFFFAOYSA-N 0.000 description 1
- ILNOEDXAWIRCKH-UHFFFAOYSA-N 6-[2-methyl-4-(1h-1,2,4-triazol-5-yl)phenyl]-4-(oxan-4-ylmethyl)spiro[1h-pyrazino[2,3-b]pyrazine-3,1'-cyclobutane]-2-one Chemical compound CC1=CC(C=2NC=NN=2)=CC=C1C(N=C1N2CC3CCOCC3)=CN=C1NC(=O)C12CCC1 ILNOEDXAWIRCKH-UHFFFAOYSA-N 0.000 description 1
- PJQVEQKFGGSAEV-UHFFFAOYSA-N 6-[2-methyl-4-(1h-1,2,4-triazol-5-yl)phenyl]-4-(oxan-4-ylmethyl)spiro[1h-pyrazino[2,3-b]pyrazine-3,1'-cyclopentane]-2-one Chemical compound CC1=CC(C=2NC=NN=2)=CC=C1C(N=C1N2CC3CCOCC3)=CN=C1NC(=O)C12CCCC1 PJQVEQKFGGSAEV-UHFFFAOYSA-N 0.000 description 1
- STXPSSAFZHNAFA-UHFFFAOYSA-N 6-[2-methyl-4-(1h-1,2,4-triazol-5-yl)phenyl]spiro[1,4-dihydropyrazino[2,3-b]pyrazine-3,1'-cyclobutane]-2-one Chemical compound CC1=CC(C=2NC=NN=2)=CC=C1C(N=C1N2)=CN=C1NC(=O)C12CCC1 STXPSSAFZHNAFA-UHFFFAOYSA-N 0.000 description 1
- CSGDQYPPEGPFMJ-UHFFFAOYSA-N 6-[2-methyl-4-(1h-1,2,4-triazol-5-yl)phenyl]spiro[1,4-dihydropyrazino[2,3-b]pyrazine-3,1'-cyclopentane]-2-one Chemical compound CC1=CC(C=2NC=NN=2)=CC=C1C(N=C1N2)=CN=C1NC(=O)C12CCCC1 CSGDQYPPEGPFMJ-UHFFFAOYSA-N 0.000 description 1
- VKHASUACNKVOCT-UHFFFAOYSA-N 6-[2-methyl-4-(1h-1,2,4-triazol-5-yl)phenyl]spiro[1,4-dihydropyrazino[2,3-b]pyrazine-3,1'-cyclopropane]-2-one Chemical compound CC1=CC(C=2NC=NN=2)=CC=C1C(N=C1N2)=CN=C1NC(=O)C12CC1 VKHASUACNKVOCT-UHFFFAOYSA-N 0.000 description 1
- VWKCUHUGNGSMKP-UHFFFAOYSA-N 6-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-2,2-dimethyl-4-[2-(oxan-4-yl)ethyl]-1h-pyrazino[2,3-b]pyrazin-3-one Chemical compound C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NC(C)(C)C(=O)N2CCC3CCOCC3)C2=N1 VWKCUHUGNGSMKP-UHFFFAOYSA-N 0.000 description 1
- AUOAXJCFODXAQR-UHFFFAOYSA-N 6-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-3,3-dimethyl-4-[2-(oxan-4-yl)ethyl]-1h-pyrazino[2,3-b]pyrazin-2-one Chemical compound C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NC(=O)C(C)(C)N2CCC3CCOCC3)C2=N1 AUOAXJCFODXAQR-UHFFFAOYSA-N 0.000 description 1
- MBJIUZPUSZUURH-OAHLLOKOSA-N 6-methyl-3-[(1r)-1-phenylethyl]-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1([C@@H](C)N2C(NC3=NC(C)=C(N=C32)C=2C3=CC=CN=C3C=CC=2)=O)=CC=CC=C1 MBJIUZPUSZUURH-OAHLLOKOSA-N 0.000 description 1
- MBJIUZPUSZUURH-HNNXBMFYSA-N 6-methyl-3-[(1s)-1-phenylethyl]-5-quinolin-5-yl-1h-imidazo[4,5-b]pyrazin-2-one Chemical compound C1([C@H](C)N2C(NC3=NC(C)=C(N=C32)C=2C3=CC=CN=C3C=CC=2)=O)=CC=CC=C1 MBJIUZPUSZUURH-HNNXBMFYSA-N 0.000 description 1
- WVZMHVPOOSNVDH-UHFFFAOYSA-N 6-pyridin-4-yl-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound C=1N=C2NC(=O)NC2=CC=1C1=CC=NC=C1 WVZMHVPOOSNVDH-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- SZAHUEISOMFYRT-UHFFFAOYSA-N 8-(2,2-dimethylpropyl)-2-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CC(C)(C)C)CC(=O)NC2=NC=C1C1=CC=C(C(C)(C)O)N=C1 SZAHUEISOMFYRT-UHFFFAOYSA-N 0.000 description 1
- LBQBMEVXMVNFHK-UHFFFAOYSA-N 8-(2-methoxyethyl)-2-[2-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CCOC)CC(=O)NC2=NC=C1C(C(=N1)C)=CC=C1C1=NN=CN1 LBQBMEVXMVNFHK-UHFFFAOYSA-N 0.000 description 1
- KFVVAZHOBVROKG-UHFFFAOYSA-N 8-(2-methoxyethyl)-2-[4-(1h-1,2,4-triazol-5-yl)phenyl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CCOC)CC(=O)NC2=NC=C1C(C=C1)=CC=C1C1=NN=CN1 KFVVAZHOBVROKG-UHFFFAOYSA-N 0.000 description 1
- GSTUONVZFWSEFP-UHFFFAOYSA-N 8-(2-methoxyethyl)-2-[4-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CCOC)CC(=O)NC2=NC=C1C(C(=C1)C)=CN=C1C=1N=CNN=1 GSTUONVZFWSEFP-UHFFFAOYSA-N 0.000 description 1
- NRHQSISFDUSJJZ-UHFFFAOYSA-N 8-(2-methoxyethyl)-2-[6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CCOC)CC(=O)NC2=NC=C1C(C=N1)=CC=C1C=1N=CNN=1 NRHQSISFDUSJJZ-UHFFFAOYSA-N 0.000 description 1
- BXQHXEPMIVXXOS-UHFFFAOYSA-N 8-(cyclopentylmethyl)-2-[2-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound CC1=NC(C=2NC=NN=2)=CC=C1C(N=C12)=CN=C1NC(=O)CN2CC1CCCC1 BXQHXEPMIVXXOS-UHFFFAOYSA-N 0.000 description 1
- LYLMERCWTSHTGW-UHFFFAOYSA-N 8-(oxan-4-yl)-2-[6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C12=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NC(=O)CN1C1CCOCC1 LYLMERCWTSHTGW-UHFFFAOYSA-N 0.000 description 1
- GHZNTMVDONIJMJ-UHFFFAOYSA-N 8-(oxan-4-ylmethyl)-2-[4-(1h-1,2,4-triazol-5-yl)phenyl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C12=NC(C=3C=CC(=CC=3)C=3NC=NN=3)=CN=C2NC(=O)CN1CC1CCOCC1 GHZNTMVDONIJMJ-UHFFFAOYSA-N 0.000 description 1
- PRRWMVAYVIIEBP-CHWSQXEVSA-N 8-[(1r,3r)-3-methoxycyclopentyl]-2-[2-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1[C@H](OC)CC[C@H]1N1C2=NC(C=3C(=NC(=CC=3)C=3NC=NN=3)C)=CN=C2NC(=O)C1 PRRWMVAYVIIEBP-CHWSQXEVSA-N 0.000 description 1
- PRRWMVAYVIIEBP-OLZOCXBDSA-N 8-[(1r,3s)-3-methoxycyclopentyl]-2-[2-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1[C@@H](OC)CC[C@H]1N1C2=NC(C=3C(=NC(=CC=3)C=3NC=NN=3)C)=CN=C2NC(=O)C1 PRRWMVAYVIIEBP-OLZOCXBDSA-N 0.000 description 1
- PRRWMVAYVIIEBP-QWHCGFSZSA-N 8-[(1s,3r)-3-methoxycyclopentyl]-2-[2-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1[C@H](OC)CC[C@@H]1N1C2=NC(C=3C(=NC(=CC=3)C=3NC=NN=3)C)=CN=C2NC(=O)C1 PRRWMVAYVIIEBP-QWHCGFSZSA-N 0.000 description 1
- PRRWMVAYVIIEBP-STQMWFEESA-N 8-[(1s,3s)-3-methoxycyclopentyl]-2-[2-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C(=NC(=CC=3)C=3NC=NN=3)C)=CN=C2NC(=O)C1 PRRWMVAYVIIEBP-STQMWFEESA-N 0.000 description 1
- PVPHLPKWACCKHK-UHFFFAOYSA-N 8-[2-(oxan-4-yl)ethyl]-2-(1h-pyrrolo[2,3-b]pyridin-3-yl)-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C12=NC(C=3C4=CC=CN=C4NC=3)=CN=C2NC(=O)CN1CCC1CCOCC1 PVPHLPKWACCKHK-UHFFFAOYSA-N 0.000 description 1
- SWRPWGNFTYMVQO-UHFFFAOYSA-N 8-[2-(oxan-4-yl)ethyl]-2-(1h-pyrrolo[2,3-b]pyridin-5-yl)-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C12=NC(C=3C=C4C=CNC4=NC=3)=CN=C2NC(=O)CN1CCC1CCOCC1 SWRPWGNFTYMVQO-UHFFFAOYSA-N 0.000 description 1
- WGVBIPHUSCOSGR-UHFFFAOYSA-N 8-[2-(oxan-4-yl)ethyl]-2-[3-(1h-1,2,4-triazol-5-yl)phenyl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C12=NC(C=3C=C(C=CC=3)C=3NN=CN=3)=CN=C2NC(=O)CN1CCC1CCOCC1 WGVBIPHUSCOSGR-UHFFFAOYSA-N 0.000 description 1
- MLNSAGOBCFMEKI-UHFFFAOYSA-N 8-[2-(oxan-4-yl)ethyl]-2-[4-(1h-1,2,4-triazol-5-yl)phenyl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C12=NC(C=3C=CC(=CC=3)C=3NN=CN=3)=CN=C2NC(=O)CN1CCC1CCOCC1 MLNSAGOBCFMEKI-UHFFFAOYSA-N 0.000 description 1
- RBCVZOQQBMCWAL-UHFFFAOYSA-N 8-[2-(oxan-4-yl)ethyl]-2-[6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C12=NC(C=3C=NC(=CC=3)C=3NC=NN=3)=CN=C2NC(=O)CN1CCC1CCOCC1 RBCVZOQQBMCWAL-UHFFFAOYSA-N 0.000 description 1
- IKJNTZVWDMXCEA-KGLIPLIRSA-N 8-[[(1r,3s)-3-methoxycyclopentyl]methyl]-2-[2-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1[C@@H](OC)CC[C@H]1CN1C2=NC(C=3C(=NC(=CC=3)C=3NC=NN=3)C)=CN=C2NC(=O)C1 IKJNTZVWDMXCEA-KGLIPLIRSA-N 0.000 description 1
- IKJNTZVWDMXCEA-UONOGXRCSA-N 8-[[(1s,3r)-3-methoxycyclopentyl]methyl]-2-[2-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound C1[C@H](OC)CC[C@@H]1CN1C2=NC(C=3C(=NC(=CC=3)C=3NC=NN=3)C)=CN=C2NC(=O)C1 IKJNTZVWDMXCEA-UONOGXRCSA-N 0.000 description 1
- RGGGKLOHVQCLKI-UHFFFAOYSA-N 8-ethyl-2-[2-methyl-6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CC)CC(=O)NC2=NC=C1C(C(=N1)C)=CC=C1C1=NN=CN1 RGGGKLOHVQCLKI-UHFFFAOYSA-N 0.000 description 1
- ZSMPGGSXRQZDSI-UHFFFAOYSA-N 8-ethyl-2-[4-(1h-1,2,4-triazol-5-yl)phenyl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CC)CC(=O)NC2=NC=C1C(C=C1)=CC=C1C1=NN=CN1 ZSMPGGSXRQZDSI-UHFFFAOYSA-N 0.000 description 1
- KIMIJUKZUGPJLW-UHFFFAOYSA-N 8-ethyl-2-[5-fluoro-2-methyl-4-(1h-1,2,4-triazol-5-yl)phenyl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CC)CC(=O)NC2=NC=C1C(C(=C1)C)=CC(F)=C1C=1N=CNN=1 KIMIJUKZUGPJLW-UHFFFAOYSA-N 0.000 description 1
- IJPDTFGHINPMDZ-UHFFFAOYSA-N 8-ethyl-2-[6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CC)CC(=O)NC2=NC=C1C(C=N1)=CC=C1C=1N=CNN=1 IJPDTFGHINPMDZ-UHFFFAOYSA-N 0.000 description 1
- DHVFFGOHZVFRTC-UHFFFAOYSA-N 8-methyl-6-(2-oxo-1,3-dihydroimidazo[4,5-b]pyridin-6-yl)-1h-quinolin-2-one Chemical compound N1=C2NC(=O)NC2=CC(C=2C=C(C=3NC(=O)C=CC=3C=2)C)=C1 DHVFFGOHZVFRTC-UHFFFAOYSA-N 0.000 description 1
- RYBVPTYSQORCOP-UHFFFAOYSA-N 8-oxo-2-(2-oxo-1h-pyridin-3-yl)-9-[2-(trifluoromethyl)phenyl]-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C(=NC=CC=3)O)=NC=2N1C1=CC=CC=C1C(F)(F)F RYBVPTYSQORCOP-UHFFFAOYSA-N 0.000 description 1
- ZIWRQUWKNJXBCS-UHFFFAOYSA-N 8-oxo-2-(4-oxo-1h-pyridin-3-yl)-9-[2-(trifluoromethyl)phenyl]-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C(=CC=NC=3)O)=NC=2N1C1=CC=CC=C1C(F)(F)F ZIWRQUWKNJXBCS-UHFFFAOYSA-N 0.000 description 1
- HVDQDMFALGVFGZ-UHFFFAOYSA-N 8-oxo-2-(6-oxo-1h-pyridin-3-yl)-9-[2-(trifluoromethyl)phenyl]-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=NC(O)=CC=3)=NC=2N1C1=CC=CC=C1C(F)(F)F HVDQDMFALGVFGZ-UHFFFAOYSA-N 0.000 description 1
- UVSJNMXGMPBRPB-UHFFFAOYSA-N 8-oxo-9-(2-propan-2-ylphenyl)-2-(1h-pyrrolo[2,3-b]pyridin-5-yl)-7h-purine-6-carboxamide Chemical class CC(C)C1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C4C=CNC4=NC=3)N=C21 UVSJNMXGMPBRPB-UHFFFAOYSA-N 0.000 description 1
- GKXCVPWPQLVDEH-UHFFFAOYSA-N 8-oxo-9-(2-propan-2-ylphenyl)-2-[4-(1h-1,2,4-triazol-5-yl)phenyl]-7h-purine-6-carboxamide Chemical compound CC(C)C1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=CC(=CC=3)C3=NNC=N3)N=C21 GKXCVPWPQLVDEH-UHFFFAOYSA-N 0.000 description 1
- PBUPUHCPBXBSKQ-UHFFFAOYSA-N 8-oxo-9-(2-propan-2-ylphenyl)-2-[4-(2h-triazol-4-yl)phenyl]-7h-purine-6-carboxamide Chemical compound CC(C)C1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=CC(=CC=3)C=3NN=NC=3)N=C21 PBUPUHCPBXBSKQ-UHFFFAOYSA-N 0.000 description 1
- JBGQNBLMGAVHRY-UHFFFAOYSA-N 8-oxo-9-phenyl-2-pyridin-2-yl-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3N=CC=CC=3)=NC=2N1C1=CC=CC=C1 JBGQNBLMGAVHRY-UHFFFAOYSA-N 0.000 description 1
- SPXZOEYWZLMLNF-UHFFFAOYSA-N 8-propan-2-yl-2-[6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(C(C)C)CC(=O)NC2=NC=C1C(C=N1)=CC=C1C=1N=CNN=1 SPXZOEYWZLMLNF-UHFFFAOYSA-N 0.000 description 1
- FQRXLNIVEFVHSE-UHFFFAOYSA-N 9-(2,3-dihydro-1h-inden-1-yl)-2-(3-hydroxyphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound N=1C=2N(C3C4=CC=CC=C4CC3)C(=O)NC=2C(C(=O)N)=NC=1C1=CC=CC(O)=C1 FQRXLNIVEFVHSE-UHFFFAOYSA-N 0.000 description 1
- NINLEEBDKKNBKP-UHFFFAOYSA-N 9-(2,4-dichlorophenyl)-2-(3-hydroxyphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=C(O)C=CC=3)=NC=2N1C1=CC=C(Cl)C=C1Cl NINLEEBDKKNBKP-UHFFFAOYSA-N 0.000 description 1
- RIWTVOMGWCAJRC-UHFFFAOYSA-N 9-(2,6-difluorophenyl)-2-(3-hydroxyphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=C(O)C=CC=3)=NC=2N1C1=C(F)C=CC=C1F RIWTVOMGWCAJRC-UHFFFAOYSA-N 0.000 description 1
- AOWMFNDNCWMSIW-UHFFFAOYSA-N 9-(2-chlorophenyl)-2-(3-hydroxyphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=C(O)C=CC=3)=NC=2N1C1=CC=CC=C1Cl AOWMFNDNCWMSIW-UHFFFAOYSA-N 0.000 description 1
- BQXDSXFAOYLSPZ-UHFFFAOYSA-N 9-(2-cyclohexylphenyl)-2-(3-hydroxyphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=C(O)C=CC=3)=NC=2N1C1=CC=CC=C1C1CCCCC1 BQXDSXFAOYLSPZ-UHFFFAOYSA-N 0.000 description 1
- MPZHAQZONBYNJF-UHFFFAOYSA-N 9-(2-cyclopentylphenyl)-2-(3-hydroxyphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=C(O)C=CC=3)=NC=2N1C1=CC=CC=C1C1CCCC1 MPZHAQZONBYNJF-UHFFFAOYSA-N 0.000 description 1
- ZIZGILIJVGTDJQ-UHFFFAOYSA-N 9-(2-ethylphenyl)-2-(3-hydroxyphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound CCC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C(O)C=CC=3)N=C21 ZIZGILIJVGTDJQ-UHFFFAOYSA-N 0.000 description 1
- WSSVXPRSPXJJEL-UHFFFAOYSA-N 9-(2-fluoro-3-methoxyphenyl)-2-(3-hydroxyphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound COC1=CC=CC(N2C(NC3=C(C(N)=O)N=C(N=C32)C=2C=C(O)C=CC=2)=O)=C1F WSSVXPRSPXJJEL-UHFFFAOYSA-N 0.000 description 1
- IFZDVZPSOCXLNA-UHFFFAOYSA-N 9-(2-fluoro-4-methoxyphenyl)-2-(3-hydroxyphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound FC1=CC(OC)=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C(O)C=CC=3)N=C21 IFZDVZPSOCXLNA-UHFFFAOYSA-N 0.000 description 1
- LHKPMCROXDKVPM-UHFFFAOYSA-N 9-(2-fluoro-5-methoxyphenyl)-2-(3-hydroxyphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound COC1=CC=C(F)C(N2C(NC3=C(C(N)=O)N=C(N=C32)C=2C=C(O)C=CC=2)=O)=C1 LHKPMCROXDKVPM-UHFFFAOYSA-N 0.000 description 1
- SUAKGCQXZJVTLK-UHFFFAOYSA-N 9-(2-fluorophenyl)-2-(3-hydroxyphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=C(O)C=CC=3)=NC=2N1C1=CC=CC=C1F SUAKGCQXZJVTLK-UHFFFAOYSA-N 0.000 description 1
- SEBCRFUXBLJQHQ-UHFFFAOYSA-N 9-(2-hydroxyethyl)-2-methylpurine-6-carboxamide Chemical compound CC1=NC(C(N)=O)=C2N=CN(CCO)C2=N1 SEBCRFUXBLJQHQ-UHFFFAOYSA-N 0.000 description 1
- YHAKLGLSQXIZCK-UHFFFAOYSA-N 9-(2-methoxyphenyl)-2-(2-methyl-3h-benzimidazol-5-yl)-8-oxo-7h-purine-6-carboxamide Chemical class COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C4NC(C)=NC4=CC=3)N=C21 YHAKLGLSQXIZCK-UHFFFAOYSA-N 0.000 description 1
- MLKIZPXRZCMNCL-UHFFFAOYSA-N 9-(2-methoxyphenyl)-2-(2-methylsulfanyl-3h-benzimidazol-5-yl)-8-oxo-7h-purine-6-carboxamide Chemical compound COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C4N=C(SC)NC4=CC=3)N=C21 MLKIZPXRZCMNCL-UHFFFAOYSA-N 0.000 description 1
- UGRQLZSVBQNWHA-UHFFFAOYSA-N 9-(2-methoxyphenyl)-2-(3-nitrophenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C(C=CC=3)[N+]([O-])=O)N=C21 UGRQLZSVBQNWHA-UHFFFAOYSA-N 0.000 description 1
- QMZSCBSIWQMGJK-UHFFFAOYSA-N 9-(2-methoxyphenyl)-2-(6-methoxypyridin-3-yl)-8-oxo-7h-purine-6-carboxamide Chemical compound C1=NC(OC)=CC=C1C1=NC(C(N)=O)=C(NC(=O)N2C=3C(=CC=CC=3)OC)C2=N1 QMZSCBSIWQMGJK-UHFFFAOYSA-N 0.000 description 1
- ZUHQUPKTMOTRHQ-UHFFFAOYSA-N 9-(2-methoxyphenyl)-8-oxo-2-(2-oxo-1h-pyridin-4-yl)-7h-purine-6-carboxamide Chemical compound COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C(O)N=CC=3)N=C21 ZUHQUPKTMOTRHQ-UHFFFAOYSA-N 0.000 description 1
- AUBKNUIKWUJWLF-UHFFFAOYSA-N 9-(2-methoxyphenyl)-8-oxo-2-[2-(trifluoromethyl)-3h-benzimidazol-5-yl]-7h-purine-6-carboxamide Chemical compound COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C4NC(=NC4=CC=3)C(F)(F)F)N=C21 AUBKNUIKWUJWLF-UHFFFAOYSA-N 0.000 description 1
- JZBHHJDVNJKBQT-UHFFFAOYSA-N 9-(2-methoxyphenyl)-8-oxo-2-[2-(trifluoromethyl)phenyl]-7h-purine-6-carboxamide Chemical compound COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C=3C(=CC=CC=3)C(F)(F)F)N=C21 JZBHHJDVNJKBQT-UHFFFAOYSA-N 0.000 description 1
- RKNLFSHHRWRJMY-UHFFFAOYSA-N 9-(2-methoxyphenyl)-8-oxo-2-[3-(trifluoromethoxy)phenyl]-7h-purine-6-carboxamide Chemical compound COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C(OC(F)(F)F)C=CC=3)N=C21 RKNLFSHHRWRJMY-UHFFFAOYSA-N 0.000 description 1
- GOIHNAWCURLHMV-UHFFFAOYSA-N 9-(2-methoxyphenyl)-8-oxo-2-[3-(trifluoromethyl)phenyl]-7h-purine-6-carboxamide Chemical compound COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C(C=CC=3)C(F)(F)F)N=C21 GOIHNAWCURLHMV-UHFFFAOYSA-N 0.000 description 1
- XIDQEHKOCLLHLJ-SNVBAGLBSA-N 9-(2-methoxyphenyl)-8-oxo-2-[[(2r)-pyrrolidin-2-yl]methylamino]-7h-purine-6-carboxamide Chemical compound COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(NC[C@@H]3NCCC3)N=C21 XIDQEHKOCLLHLJ-SNVBAGLBSA-N 0.000 description 1
- XIDQEHKOCLLHLJ-JTQLQIEISA-N 9-(2-methoxyphenyl)-8-oxo-2-[[(2s)-pyrrolidin-2-yl]methylamino]-7h-purine-6-carboxamide Chemical compound COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(NC[C@H]3NCCC3)N=C21 XIDQEHKOCLLHLJ-JTQLQIEISA-N 0.000 description 1
- FQWFCAUCLSFKSV-SECBINFHSA-N 9-(2-methoxyphenyl)-8-oxo-2-[[(3r)-pyrrolidin-3-yl]amino]-7h-purine-6-carboxamide Chemical compound COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(N[C@H]3CNCC3)N=C21 FQWFCAUCLSFKSV-SECBINFHSA-N 0.000 description 1
- FQWFCAUCLSFKSV-VIFPVBQESA-N 9-(2-methoxyphenyl)-8-oxo-2-[[(3s)-pyrrolidin-3-yl]amino]-7h-purine-6-carboxamide Chemical compound COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(N[C@@H]3CNCC3)N=C21 FQWFCAUCLSFKSV-VIFPVBQESA-N 0.000 description 1
- AGLIYPCDJKUNQG-UHFFFAOYSA-N 9-(2-methoxyphenyl)-8-oxo-2-pyridin-4-yl-7h-purine-6-carboxamide Chemical compound COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=CN=CC=3)N=C21 AGLIYPCDJKUNQG-UHFFFAOYSA-N 0.000 description 1
- BCPJYICCAMLZSA-UHFFFAOYSA-N 9-(2-methoxyphenyl)-8-oxo-2-quinolin-5-yl-7h-purine-6-carboxamide Chemical compound COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(C=3C4=CC=CN=C4C=CC=3)N=C21 BCPJYICCAMLZSA-UHFFFAOYSA-N 0.000 description 1
- HMCPWRONXIQANG-UHFFFAOYSA-N 9-(3-fluorophenyl)-2-(3-hydroxyphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=C(O)C=CC=3)=NC=2N1C1=CC=CC(F)=C1 HMCPWRONXIQANG-UHFFFAOYSA-N 0.000 description 1
- YJFVREULJVJAFG-UHFFFAOYSA-N 9-(cyclohexylmethyl)-2-(3-hydroxyphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=C(O)C=CC=3)=NC=2N1CC1CCCCC1 YJFVREULJVJAFG-UHFFFAOYSA-N 0.000 description 1
- OTYVVIIBUQVJFU-UHFFFAOYSA-N 9-benzyl-2-(3-hydroxyphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=C(O)C=CC=3)=NC=2N1CC1=CC=CC=C1 OTYVVIIBUQVJFU-UHFFFAOYSA-N 0.000 description 1
- JRCFAROYAPNJQJ-UHFFFAOYSA-N 9-benzyl-8-oxo-2-pyridin-3-yl-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=NC=CC=3)=NC=2N1CC1=CC=CC=C1 JRCFAROYAPNJQJ-UHFFFAOYSA-N 0.000 description 1
- KSDCBHGJKJWKKW-UHFFFAOYSA-N 9-cycloheptyl-8-oxo-2-pyridin-3-yl-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=NC=CC=3)=NC=2N1C1CCCCCC1 KSDCBHGJKJWKKW-UHFFFAOYSA-N 0.000 description 1
- TZEFXCMQGLWLKS-UHFFFAOYSA-N 9-cyclohexyl-2-(1h-imidazo[4,5-b]pyridin-6-yl)-8-oxo-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=C4NC=NC4=NC=3)=NC=2N1C1CCCCC1 TZEFXCMQGLWLKS-UHFFFAOYSA-N 0.000 description 1
- IDOABCJJJSSICD-UHFFFAOYSA-N 9-cyclohexyl-2-(3-hydroxyphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=C(O)C=CC=3)=NC=2N1C1CCCCC1 IDOABCJJJSSICD-UHFFFAOYSA-N 0.000 description 1
- OMKVBXCEVLUFAK-UHFFFAOYSA-N 9-cyclohexyl-8-oxo-2-[4-(1h-1,2,4-triazol-5-yl)phenyl]-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=CC(=CC=3)C3=NNC=N3)=NC=2N1C1CCCCC1 OMKVBXCEVLUFAK-UHFFFAOYSA-N 0.000 description 1
- OWYNYCCFQVSEKU-UHFFFAOYSA-N 9-cyclopentyl-2-(3-hydroxyphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N)=NC(C=3C=C(O)C=CC=3)=NC=2N1C1CCCC1 OWYNYCCFQVSEKU-UHFFFAOYSA-N 0.000 description 1
- DKWQALXHTVXPHP-UHFFFAOYSA-N 9-methyl-8-oxo-2-pyridin-3-yl-7h-purine-6-carboxamide Chemical compound N=1C(C(N)=O)=C2NC(=O)N(C)C2=NC=1C1=CC=CN=C1 DKWQALXHTVXPHP-UHFFFAOYSA-N 0.000 description 1
- AENLBSGSASHWDU-UHFFFAOYSA-N 9-phenyl-2-pyridin-3-ylpurine-6-carboxamide Chemical compound C1=NC=2C(C(=O)N)=NC(C=3C=NC=CC=3)=NC=2N1C1=CC=CC=C1 AENLBSGSASHWDU-UHFFFAOYSA-N 0.000 description 1
- REZHZXQCNPZUFE-UHFFFAOYSA-N 9-tert-butyl-2-(3-hydroxyphenyl)-8-oxo-7h-purine-6-carboxamide Chemical compound N=1C(C(N)=O)=C2NC(=O)N(C(C)(C)C)C2=NC=1C1=CC=CC(O)=C1 REZHZXQCNPZUFE-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 208000031261 Acute myeloid leukaemia Diseases 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 108010082126 Alanine transaminase Proteins 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 208000017925 Askin tumor Diseases 0.000 description 1
- 108010003415 Aspartate Aminotransferases Proteins 0.000 description 1
- 102000004625 Aspartate Aminotransferases Human genes 0.000 description 1
- 206010003571 Astrocytoma Diseases 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 229940122361 Bisphosphonate Drugs 0.000 description 1
- 206010005949 Bone cancer Diseases 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BUANBFSHTYULTI-UHFFFAOYSA-N C1(CCCCC1)CN1C(NC=2C1=NC(=CN2)C=2C=C1C=NC(C1=CC2)=O)=O Chemical compound C1(CCCCC1)CN1C(NC=2C1=NC(=CN2)C=2C=C1C=NC(C1=CC2)=O)=O BUANBFSHTYULTI-UHFFFAOYSA-N 0.000 description 1
- DWLJVUMDUSLYKR-HDJSIYSDSA-N C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NC(=O)CN2[C@@H]3CC[C@@H](O)CC3)C2=N1 Chemical compound C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NC(=O)CN2[C@@H]3CC[C@@H](O)CC3)C2=N1 DWLJVUMDUSLYKR-HDJSIYSDSA-N 0.000 description 1
- DWLJVUMDUSLYKR-OKILXGFUSA-N C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NC(=O)CN2[C@H]3CC[C@@H](O)CC3)C2=N1 Chemical compound C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NC(=O)CN2[C@H]3CC[C@@H](O)CC3)C2=N1 DWLJVUMDUSLYKR-OKILXGFUSA-N 0.000 description 1
- KTLFTPMXQQIXMP-HDJSIYSDSA-N C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NCC(=O)N2[C@@H]3CC[C@@H](O)CC3)C2=N1 Chemical compound C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NCC(=O)N2[C@@H]3CC[C@@H](O)CC3)C2=N1 KTLFTPMXQQIXMP-HDJSIYSDSA-N 0.000 description 1
- KTLFTPMXQQIXMP-OKILXGFUSA-N C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NCC(=O)N2[C@H]3CC[C@@H](O)CC3)C2=N1 Chemical compound C1=NC(C(C)(O)C)=CC=C1C1=CN=C(NCC(=O)N2[C@H]3CC[C@@H](O)CC3)C2=N1 KTLFTPMXQQIXMP-OKILXGFUSA-N 0.000 description 1
- ZLNBWRIUBYDYQS-BJHJDKERSA-N C1C[C@@H](COC)CC[C@H]1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C(O)C=CC=3)N=C21 Chemical compound C1C[C@@H](COC)CC[C@H]1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C(O)C=CC=3)N=C21 ZLNBWRIUBYDYQS-BJHJDKERSA-N 0.000 description 1
- XMLNCNLPPWLQFT-XYPYZODXSA-N C1C[C@@H](N)CC[C@@H]1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C(O)C=CC=3)N=C21 Chemical compound C1C[C@@H](N)CC[C@@H]1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C(O)C=CC=3)N=C21 XMLNCNLPPWLQFT-XYPYZODXSA-N 0.000 description 1
- TZHUXNWOSOSEOU-MQMHXKEQSA-N C1C[C@@H](O)CC[C@@H]1CN1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NC(=O)C1 Chemical compound C1C[C@@H](O)CC[C@@H]1CN1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NC(=O)C1 TZHUXNWOSOSEOU-MQMHXKEQSA-N 0.000 description 1
- HNRUHUMESXAVSX-MQMHXKEQSA-N C1C[C@@H](O)CC[C@@H]1CN1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NCC1=O Chemical compound C1C[C@@H](O)CC[C@@H]1CN1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NCC1=O HNRUHUMESXAVSX-MQMHXKEQSA-N 0.000 description 1
- ABLFRLHGLALIJS-JOCQHMNTSA-N C1C[C@@H](O)CC[C@@H]1N1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NC(=O)C1 Chemical compound C1C[C@@H](O)CC[C@@H]1N1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NC(=O)C1 ABLFRLHGLALIJS-JOCQHMNTSA-N 0.000 description 1
- ZADHRFJEWSWHTM-JOCQHMNTSA-N C1C[C@@H](O)CC[C@@H]1N1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NCC1=O Chemical compound C1C[C@@H](O)CC[C@@H]1N1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NCC1=O ZADHRFJEWSWHTM-JOCQHMNTSA-N 0.000 description 1
- TZHUXNWOSOSEOU-XBXGTLAGSA-N C1C[C@@H](O)CC[C@H]1CN1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NC(=O)C1 Chemical compound C1C[C@@H](O)CC[C@H]1CN1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NC(=O)C1 TZHUXNWOSOSEOU-XBXGTLAGSA-N 0.000 description 1
- HNRUHUMESXAVSX-XBXGTLAGSA-N C1C[C@@H](O)CC[C@H]1CN1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NCC1=O Chemical compound C1C[C@@H](O)CC[C@H]1CN1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NCC1=O HNRUHUMESXAVSX-XBXGTLAGSA-N 0.000 description 1
- ABLFRLHGLALIJS-BETUJISGSA-N C1C[C@@H](O)CC[C@H]1N1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NC(=O)C1 Chemical compound C1C[C@@H](O)CC[C@H]1N1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NC(=O)C1 ABLFRLHGLALIJS-BETUJISGSA-N 0.000 description 1
- ZADHRFJEWSWHTM-BETUJISGSA-N C1C[C@@H](O)CC[C@H]1N1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NCC1=O Chemical compound C1C[C@@H](O)CC[C@H]1N1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NCC1=O ZADHRFJEWSWHTM-BETUJISGSA-N 0.000 description 1
- SPGRJRJDZVPGOT-SHTZXODSSA-N C1C[C@@H](OC)CC[C@@H]1CN1C2=NC(C=3C(=CC(=C(F)C=3)C3=NNC=N3)C)=CN=C2NC(=O)C1 Chemical compound C1C[C@@H](OC)CC[C@@H]1CN1C2=NC(C=3C(=CC(=C(F)C=3)C3=NNC=N3)C)=CN=C2NC(=O)C1 SPGRJRJDZVPGOT-SHTZXODSSA-N 0.000 description 1
- ZNYMSBFVLLHDJP-SHTZXODSSA-N C1C[C@@H](OC)CC[C@@H]1CN1C2=NC(C=3C(=CC(=C(F)C=3)C3=NNC=N3)C)=CN=C2NCC1=O Chemical compound C1C[C@@H](OC)CC[C@@H]1CN1C2=NC(C=3C(=CC(=C(F)C=3)C3=NNC=N3)C)=CN=C2NCC1=O ZNYMSBFVLLHDJP-SHTZXODSSA-N 0.000 description 1
- KTKQRDMDJDFELL-HDJSIYSDSA-N C1C[C@@H](OC)CC[C@@H]1CN1C2=NC(C=3C(=CC(=NC=3)C(N)=O)C)=CN=C2NCC1=O Chemical compound C1C[C@@H](OC)CC[C@@H]1CN1C2=NC(C=3C(=CC(=NC=3)C(N)=O)C)=CN=C2NCC1=O KTKQRDMDJDFELL-HDJSIYSDSA-N 0.000 description 1
- NRKHRXABMIBGEW-SHTZXODSSA-N C1C[C@@H](OC)CC[C@@H]1CN1C2=NC(C=3C(=CC(=NC=3)C3=NNC=N3)C)=CN=C2NCC1=O Chemical compound C1C[C@@H](OC)CC[C@@H]1CN1C2=NC(C=3C(=CC(=NC=3)C3=NNC=N3)C)=CN=C2NCC1=O NRKHRXABMIBGEW-SHTZXODSSA-N 0.000 description 1
- KVEPKTYZFVUHKX-SHTZXODSSA-N C1C[C@@H](OC)CC[C@@H]1CN1C2=NC(C=3C(=NC(=CC=3)C3=NNC=N3)C)=CN=C2NCC1=O Chemical compound C1C[C@@H](OC)CC[C@@H]1CN1C2=NC(C=3C(=NC(=CC=3)C3=NNC=N3)C)=CN=C2NCC1=O KVEPKTYZFVUHKX-SHTZXODSSA-N 0.000 description 1
- CXTSHKNYOVLEJT-RZDIXWSQSA-N C1C[C@@H](OC)CC[C@@H]1CN1C2=NC(C=3C=CC(=CC=3)C(C)(C)O)=CN=C2NC(=O)C1 Chemical compound C1C[C@@H](OC)CC[C@@H]1CN1C2=NC(C=3C=CC(=CC=3)C(C)(C)O)=CN=C2NC(=O)C1 CXTSHKNYOVLEJT-RZDIXWSQSA-N 0.000 description 1
- NPBANVRWVVVQJV-KOMQPUFPSA-N C1C[C@@H](OC)CC[C@@H]1CN1C2=NC(C=3C=NC(=CC=3)C(C)(C)O)=CN=C2NC(=O)C1 Chemical compound C1C[C@@H](OC)CC[C@@H]1CN1C2=NC(C=3C=NC(=CC=3)C(C)(C)O)=CN=C2NC(=O)C1 NPBANVRWVVVQJV-KOMQPUFPSA-N 0.000 description 1
- KXDXRGGNJRTDPF-KOMQPUFPSA-N C1C[C@@H](OC)CC[C@@H]1CN1C2=NC(C=3C=NC(=CC=3)C(C)(C)O)=CN=C2NCC1=O Chemical compound C1C[C@@H](OC)CC[C@@H]1CN1C2=NC(C=3C=NC(=CC=3)C(C)(C)O)=CN=C2NCC1=O KXDXRGGNJRTDPF-KOMQPUFPSA-N 0.000 description 1
- IEJOOKMBLTZCSH-CTYIDZIISA-N C1C[C@@H](OC)CC[C@@H]1CN1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NC(=O)C1 Chemical compound C1C[C@@H](OC)CC[C@@H]1CN1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NC(=O)C1 IEJOOKMBLTZCSH-CTYIDZIISA-N 0.000 description 1
- ZNBIWMFZTYSTHE-CTYIDZIISA-N C1C[C@@H](OC)CC[C@@H]1CN1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NCC1=O Chemical compound C1C[C@@H](OC)CC[C@@H]1CN1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NCC1=O ZNBIWMFZTYSTHE-CTYIDZIISA-N 0.000 description 1
- FKEBCODXEMZWJX-AULYBMBSSA-N C1C[C@@H](OC)CC[C@@H]1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C(O)C=CC=3)N=C21 Chemical compound C1C[C@@H](OC)CC[C@@H]1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C(O)C=CC=3)N=C21 FKEBCODXEMZWJX-AULYBMBSSA-N 0.000 description 1
- LWEANEUUPMFOAV-HDJSIYSDSA-N C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C(=C(F)C(C4=NNC=N4)=CC=3)C)=CN=C2NC(=O)C1 Chemical compound C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C(=C(F)C(C4=NNC=N4)=CC=3)C)=CN=C2NC(=O)C1 LWEANEUUPMFOAV-HDJSIYSDSA-N 0.000 description 1
- PEQCVXULHGVULI-HDJSIYSDSA-N C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C(=CC(=C(F)C=3)C3=NNC=N3)C)=CN=C2NC(=O)C1 Chemical compound C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C(=CC(=C(F)C=3)C3=NNC=N3)C)=CN=C2NC(=O)C1 PEQCVXULHGVULI-HDJSIYSDSA-N 0.000 description 1
- IQBLMUACDDUKHT-HDJSIYSDSA-N C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C(=CC(=C(F)C=3)C3=NNC=N3)C)=CN=C2NCC1=O Chemical compound C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C(=CC(=C(F)C=3)C3=NNC=N3)C)=CN=C2NCC1=O IQBLMUACDDUKHT-HDJSIYSDSA-N 0.000 description 1
- OKXFJZPFOWVLJA-SHTZXODSSA-N C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C(=CC(=NC=3)C(C)(C)O)C)=CN=C2NC(=O)C1 Chemical compound C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C(=CC(=NC=3)C(C)(C)O)C)=CN=C2NC(=O)C1 OKXFJZPFOWVLJA-SHTZXODSSA-N 0.000 description 1
- FUXWSETYLSIMOM-HDJSIYSDSA-N C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C(=CC(=NC=3)C3=NNC=N3)C)=CN=C2NCC1=O Chemical compound C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C(=CC(=NC=3)C3=NNC=N3)C)=CN=C2NCC1=O FUXWSETYLSIMOM-HDJSIYSDSA-N 0.000 description 1
- JKTYSPNFRTWOKB-SHTZXODSSA-N C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C(=NC(=CC=3)C(C)(C)O)C)=CN=C2NC(=O)C1 Chemical compound C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C(=NC(=CC=3)C(C)(C)O)C)=CN=C2NC(=O)C1 JKTYSPNFRTWOKB-SHTZXODSSA-N 0.000 description 1
- AHTXWEHJMLNLGH-HDJSIYSDSA-N C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C(=NC(=CC=3)C=3NC=NN=3)C)=CN=C2NC(=O)C1 Chemical compound C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C(=NC(=CC=3)C=3NC=NN=3)C)=CN=C2NC(=O)C1 AHTXWEHJMLNLGH-HDJSIYSDSA-N 0.000 description 1
- DXYGEHPPAYSYLJ-HDJSIYSDSA-N C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C(=NC(=CC=3)C=3NC=NN=3)C)=CN=C2NCC1=O Chemical compound C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C(=NC(=CC=3)C=3NC=NN=3)C)=CN=C2NCC1=O DXYGEHPPAYSYLJ-HDJSIYSDSA-N 0.000 description 1
- ZDJQARYZMONTRY-QAQDUYKDSA-N C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C=CC(=CC=3)C(C)(C)O)=CN=C2NC(=O)C1 Chemical compound C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C=CC(=CC=3)C(C)(C)O)=CN=C2NC(=O)C1 ZDJQARYZMONTRY-QAQDUYKDSA-N 0.000 description 1
- BQWNQORJQWSVMS-QAQDUYKDSA-N C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C=CC(=CC=3)C(C)(C)O)=CN=C2NCC1=O Chemical compound C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C=CC(=CC=3)C(C)(C)O)=CN=C2NCC1=O BQWNQORJQWSVMS-QAQDUYKDSA-N 0.000 description 1
- ZGLONRFJOSBXER-SHTZXODSSA-N C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C=NC(=CC=3)C(C)(C)O)=CN=C2NC(=O)C1 Chemical compound C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C=NC(=CC=3)C(C)(C)O)=CN=C2NC(=O)C1 ZGLONRFJOSBXER-SHTZXODSSA-N 0.000 description 1
- 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 compound 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 description 1
- ZEGQEBXPUDXWGO-HDJSIYSDSA-N C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NC(=O)C1 Chemical compound C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NC(=O)C1 ZEGQEBXPUDXWGO-HDJSIYSDSA-N 0.000 description 1
- MVBGDSJVWDIFQJ-HDJSIYSDSA-N C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NCC1=O Chemical compound C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NCC1=O MVBGDSJVWDIFQJ-HDJSIYSDSA-N 0.000 description 1
- XTQFYGUDDGJCCH-SHTZXODSSA-N C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C=[N+]([O-])C(=CC=3)C(C)(C)O)=CN=C2NCC1=O Chemical compound C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C=[N+]([O-])C(=CC=3)C(C)(C)O)=CN=C2NCC1=O XTQFYGUDDGJCCH-SHTZXODSSA-N 0.000 description 1
- FKEBCODXEMZWJX-BJHJDKERSA-N C1C[C@@H](OC)CC[C@H]1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C(O)C=CC=3)N=C21 Chemical compound C1C[C@@H](OC)CC[C@H]1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C(O)C=CC=3)N=C21 FKEBCODXEMZWJX-BJHJDKERSA-N 0.000 description 1
- OACQOYQOCHYLIO-TXEJJXNPSA-N C1C[C@@H](OC)CC[C@H]1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C4NC=NC4=CC=3)N=C21 Chemical compound C1C[C@@H](OC)CC[C@H]1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C4NC=NC4=CC=3)N=C21 OACQOYQOCHYLIO-TXEJJXNPSA-N 0.000 description 1
- MWYUHAJVGBDBLW-PHIMTYICSA-N C1C[C@@H](OC)CC[C@H]1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C4NC=NC4=NC=3)N=C21 Chemical compound C1C[C@@H](OC)CC[C@H]1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=C4NC=NC4=NC=3)N=C21 MWYUHAJVGBDBLW-PHIMTYICSA-N 0.000 description 1
- XAKGVAYWWIGJRU-OKILXGFUSA-N C1C[C@@H](OC)CC[C@H]1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=CC(=CC=3)C3=NNC=N3)N=C21 Chemical compound C1C[C@@H](OC)CC[C@H]1N1C(=O)NC2=C(C(N)=O)N=C(C=3C=CC(=CC=3)C3=NNC=N3)N=C21 XAKGVAYWWIGJRU-OKILXGFUSA-N 0.000 description 1
- LWEANEUUPMFOAV-OKILXGFUSA-N C1C[C@@H](OC)CC[C@H]1N1C2=NC(C=3C(=C(F)C(C4=NNC=N4)=CC=3)C)=CN=C2NC(=O)C1 Chemical compound C1C[C@@H](OC)CC[C@H]1N1C2=NC(C=3C(=C(F)C(C4=NNC=N4)=CC=3)C)=CN=C2NC(=O)C1 LWEANEUUPMFOAV-OKILXGFUSA-N 0.000 description 1
- PEQCVXULHGVULI-OKILXGFUSA-N C1C[C@@H](OC)CC[C@H]1N1C2=NC(C=3C(=CC(=C(F)C=3)C3=NNC=N3)C)=CN=C2NC(=O)C1 Chemical compound C1C[C@@H](OC)CC[C@H]1N1C2=NC(C=3C(=CC(=C(F)C=3)C3=NNC=N3)C)=CN=C2NC(=O)C1 PEQCVXULHGVULI-OKILXGFUSA-N 0.000 description 1
- AHTXWEHJMLNLGH-OKILXGFUSA-N C1C[C@@H](OC)CC[C@H]1N1C2=NC(C=3C(=NC(=CC=3)C=3NC=NN=3)C)=CN=C2NC(=O)C1 Chemical compound C1C[C@@H](OC)CC[C@H]1N1C2=NC(C=3C(=NC(=CC=3)C=3NC=NN=3)C)=CN=C2NC(=O)C1 AHTXWEHJMLNLGH-OKILXGFUSA-N 0.000 description 1
- ZGLONRFJOSBXER-GASCZTMLSA-N C1C[C@@H](OC)CC[C@H]1N1C2=NC(C=3C=NC(=CC=3)C(C)(C)O)=CN=C2NC(=O)C1 Chemical compound C1C[C@@H](OC)CC[C@H]1N1C2=NC(C=3C=NC(=CC=3)C(C)(C)O)=CN=C2NC(=O)C1 ZGLONRFJOSBXER-GASCZTMLSA-N 0.000 description 1
- ZEGQEBXPUDXWGO-OKILXGFUSA-N C1C[C@@H](OC)CC[C@H]1N1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NC(=O)C1 Chemical compound C1C[C@@H](OC)CC[C@H]1N1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NC(=O)C1 ZEGQEBXPUDXWGO-OKILXGFUSA-N 0.000 description 1
- MVBGDSJVWDIFQJ-OKILXGFUSA-N C1C[C@@H](OC)CC[C@H]1N1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NCC1=O Chemical compound C1C[C@@H](OC)CC[C@H]1N1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NCC1=O MVBGDSJVWDIFQJ-OKILXGFUSA-N 0.000 description 1
- SPGRJRJDZVPGOT-GASCZTMLSA-N C1C[C@H](OC)CC[C@@H]1CN1C2=NC(C=3C(=CC(=C(F)C=3)C3=NNC=N3)C)=CN=C2NC(=O)C1 Chemical compound C1C[C@H](OC)CC[C@@H]1CN1C2=NC(C=3C(=CC(=C(F)C=3)C3=NNC=N3)C)=CN=C2NC(=O)C1 SPGRJRJDZVPGOT-GASCZTMLSA-N 0.000 description 1
- ZNYMSBFVLLHDJP-GASCZTMLSA-N C1C[C@H](OC)CC[C@@H]1CN1C2=NC(C=3C(=CC(=C(F)C=3)C3=NNC=N3)C)=CN=C2NCC1=O Chemical compound C1C[C@H](OC)CC[C@@H]1CN1C2=NC(C=3C(=CC(=C(F)C=3)C3=NNC=N3)C)=CN=C2NCC1=O ZNYMSBFVLLHDJP-GASCZTMLSA-N 0.000 description 1
- KTKQRDMDJDFELL-OKILXGFUSA-N C1C[C@H](OC)CC[C@@H]1CN1C2=NC(C=3C(=CC(=NC=3)C(N)=O)C)=CN=C2NCC1=O Chemical compound C1C[C@H](OC)CC[C@@H]1CN1C2=NC(C=3C(=CC(=NC=3)C(N)=O)C)=CN=C2NCC1=O KTKQRDMDJDFELL-OKILXGFUSA-N 0.000 description 1
- KVEPKTYZFVUHKX-GASCZTMLSA-N C1C[C@H](OC)CC[C@@H]1CN1C2=NC(C=3C(=NC(=CC=3)C3=NNC=N3)C)=CN=C2NCC1=O Chemical compound C1C[C@H](OC)CC[C@@H]1CN1C2=NC(C=3C(=NC(=CC=3)C3=NNC=N3)C)=CN=C2NCC1=O KVEPKTYZFVUHKX-GASCZTMLSA-N 0.000 description 1
- NPBANVRWVVVQJV-FZNQNYSPSA-N C1C[C@H](OC)CC[C@@H]1CN1C2=NC(C=3C=NC(=CC=3)C(C)(C)O)=CN=C2NC(=O)C1 Chemical compound C1C[C@H](OC)CC[C@@H]1CN1C2=NC(C=3C=NC(=CC=3)C(C)(C)O)=CN=C2NC(=O)C1 NPBANVRWVVVQJV-FZNQNYSPSA-N 0.000 description 1
- KXDXRGGNJRTDPF-FZNQNYSPSA-N C1C[C@H](OC)CC[C@@H]1CN1C2=NC(C=3C=NC(=CC=3)C(C)(C)O)=CN=C2NCC1=O Chemical compound C1C[C@H](OC)CC[C@@H]1CN1C2=NC(C=3C=NC(=CC=3)C(C)(C)O)=CN=C2NCC1=O KXDXRGGNJRTDPF-FZNQNYSPSA-N 0.000 description 1
- IEJOOKMBLTZCSH-OTVXOJSOSA-N C1C[C@H](OC)CC[C@@H]1CN1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NC(=O)C1 Chemical compound C1C[C@H](OC)CC[C@@H]1CN1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NC(=O)C1 IEJOOKMBLTZCSH-OTVXOJSOSA-N 0.000 description 1
- ZNBIWMFZTYSTHE-OTVXOJSOSA-N C1C[C@H](OC)CC[C@@H]1CN1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NCC1=O Chemical compound C1C[C@H](OC)CC[C@@H]1CN1C2=NC(C=3C=NC(=CC=3)C3=NNC=N3)=CN=C2NCC1=O ZNBIWMFZTYSTHE-OTVXOJSOSA-N 0.000 description 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 1
- BIYXBMJPSRSLCH-BETUJISGSA-N CC1=NC(C=2NC=NN=2)=CC=C1C(N=C12)=CN=C1NCC(=O)N2[C@@H]1CC[C@H](O)CC1 Chemical compound CC1=NC(C=2NC=NN=2)=CC=C1C(N=C12)=CN=C1NCC(=O)N2[C@@H]1CC[C@H](O)CC1 BIYXBMJPSRSLCH-BETUJISGSA-N 0.000 description 1
- BIYXBMJPSRSLCH-JOCQHMNTSA-N CC1=NC(C=2NC=NN=2)=CC=C1C(N=C12)=CN=C1NCC(=O)N2[C@H]1CC[C@H](O)CC1 Chemical compound CC1=NC(C=2NC=NN=2)=CC=C1C(N=C12)=CN=C1NCC(=O)N2[C@H]1CC[C@H](O)CC1 BIYXBMJPSRSLCH-JOCQHMNTSA-N 0.000 description 1
- XMJYDDXJBNFUMN-XYPYZODXSA-N COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(N[C@@H]3CC[C@@H](O)CC3)N=C21 Chemical compound COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(N[C@@H]3CC[C@@H](O)CC3)N=C21 XMJYDDXJBNFUMN-XYPYZODXSA-N 0.000 description 1
- XMJYDDXJBNFUMN-PHIMTYICSA-N COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(N[C@H]3CC[C@@H](O)CC3)N=C21 Chemical compound COC1=CC=CC=C1N1C(=O)NC2=C(C(N)=O)N=C(N[C@H]3CC[C@@H](O)CC3)N=C21 XMJYDDXJBNFUMN-PHIMTYICSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000000419 Chronic Hepatitis B Diseases 0.000 description 1
- 208000000668 Chronic Pancreatitis Diseases 0.000 description 1
- 208000006154 Chronic hepatitis C Diseases 0.000 description 1
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 108020004414 DNA Proteins 0.000 description 1
- 230000004568 DNA-binding Effects 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 102100039563 ETS translocation variant 1 Human genes 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- DFHJIYKBSFMGTL-HDJSIYSDSA-N FC=1C=C(C=2N=C3N(C[C@@H]4CC[C@@H](O)CC4)C(=O)CNC3=NC=2)C(C)=CC=1C=1N=CNN=1 Chemical compound FC=1C=C(C=2N=C3N(C[C@@H]4CC[C@@H](O)CC4)C(=O)CNC3=NC=2)C(C)=CC=1C=1N=CNN=1 DFHJIYKBSFMGTL-HDJSIYSDSA-N 0.000 description 1
- PDWFKNLSEZQKMO-HDJSIYSDSA-N FC=1C=C(C=2N=C3N(C[C@@H]4CC[C@@H](O)CC4)CC(=O)NC3=NC=2)C(C)=CC=1C=1N=CNN=1 Chemical compound FC=1C=C(C=2N=C3N(C[C@@H]4CC[C@@H](O)CC4)CC(=O)NC3=NC=2)C(C)=CC=1C=1N=CNN=1 PDWFKNLSEZQKMO-HDJSIYSDSA-N 0.000 description 1
- DFHJIYKBSFMGTL-OKILXGFUSA-N FC=1C=C(C=2N=C3N(C[C@H]4CC[C@@H](O)CC4)C(=O)CNC3=NC=2)C(C)=CC=1C=1N=CNN=1 Chemical compound FC=1C=C(C=2N=C3N(C[C@H]4CC[C@@H](O)CC4)C(=O)CNC3=NC=2)C(C)=CC=1C=1N=CNN=1 DFHJIYKBSFMGTL-OKILXGFUSA-N 0.000 description 1
- PDWFKNLSEZQKMO-OKILXGFUSA-N FC=1C=C(C=2N=C3N(C[C@H]4CC[C@@H](O)CC4)CC(=O)NC3=NC=2)C(C)=CC=1C=1N=CNN=1 Chemical compound FC=1C=C(C=2N=C3N(C[C@H]4CC[C@@H](O)CC4)CC(=O)NC3=NC=2)C(C)=CC=1C=1N=CNN=1 PDWFKNLSEZQKMO-OKILXGFUSA-N 0.000 description 1
- BVPODDRJFGBSDV-JOCQHMNTSA-N FC=1C=C(C=2N=C3N([C@@H]4CC[C@@H](O)CC4)C(=O)CNC3=NC=2)C(C)=CC=1C=1N=CNN=1 Chemical compound FC=1C=C(C=2N=C3N([C@@H]4CC[C@@H](O)CC4)C(=O)CNC3=NC=2)C(C)=CC=1C=1N=CNN=1 BVPODDRJFGBSDV-JOCQHMNTSA-N 0.000 description 1
- NCYPXMZZCBFOHU-JOCQHMNTSA-N FC=1C=C(C=2N=C3N([C@@H]4CC[C@@H](O)CC4)CC(=O)NC3=NC=2)C(C)=CC=1C=1N=CNN=1 Chemical compound FC=1C=C(C=2N=C3N([C@@H]4CC[C@@H](O)CC4)CC(=O)NC3=NC=2)C(C)=CC=1C=1N=CNN=1 NCYPXMZZCBFOHU-JOCQHMNTSA-N 0.000 description 1
- BVPODDRJFGBSDV-BETUJISGSA-N FC=1C=C(C=2N=C3N([C@H]4CC[C@@H](O)CC4)C(=O)CNC3=NC=2)C(C)=CC=1C=1N=CNN=1 Chemical compound FC=1C=C(C=2N=C3N([C@H]4CC[C@@H](O)CC4)C(=O)CNC3=NC=2)C(C)=CC=1C=1N=CNN=1 BVPODDRJFGBSDV-BETUJISGSA-N 0.000 description 1
- NCYPXMZZCBFOHU-BETUJISGSA-N FC=1C=C(C=2N=C3N([C@H]4CC[C@@H](O)CC4)CC(=O)NC3=NC=2)C(C)=CC=1C=1N=CNN=1 Chemical compound FC=1C=C(C=2N=C3N([C@H]4CC[C@@H](O)CC4)CC(=O)NC3=NC=2)C(C)=CC=1C=1N=CNN=1 NCYPXMZZCBFOHU-BETUJISGSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 102100030334 Friend leukemia integration 1 transcription factor Human genes 0.000 description 1
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 1
- 101001077417 Gallus gallus Potassium voltage-gated channel subfamily H member 6 Proteins 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 229920002907 Guar gum Polymers 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 208000031886 HIV Infections Diseases 0.000 description 1
- 208000037357 HIV infectious disease Diseases 0.000 description 1
- 102000001554 Hemoglobins Human genes 0.000 description 1
- 108010054147 Hemoglobins Proteins 0.000 description 1
- 206010019695 Hepatic neoplasm Diseases 0.000 description 1
- 208000005176 Hepatitis C Diseases 0.000 description 1
- 208000017605 Hodgkin disease nodular sclerosis Diseases 0.000 description 1
- 101000813729 Homo sapiens ETS translocation variant 1 Proteins 0.000 description 1
- 101001062996 Homo sapiens Friend leukemia integration 1 transcription factor Proteins 0.000 description 1
- 101000623857 Homo sapiens Serine/threonine-protein kinase mTOR Proteins 0.000 description 1
- 101001010792 Homo sapiens Transcriptional regulator ERG Proteins 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 description 1
- 206010023439 Kidney transplant rejection Diseases 0.000 description 1
- SKCKOFZKJLZSFA-UHFFFAOYSA-N L-Gulomethylit Natural products CC(O)C(O)C(O)C(O)CO SKCKOFZKJLZSFA-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- 125000002842 L-seryl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])O[H] 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 206010025476 Malabsorption Diseases 0.000 description 1
- 208000004155 Malabsorption Syndromes Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- 206010028289 Muscle atrophy Diseases 0.000 description 1
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 description 1
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 description 1
- HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 1
- BKAYIFDRRZZKNF-VIFPVBQESA-N N-acetylcarnosine Chemical compound CC(=O)NCCC(=O)N[C@H](C(O)=O)CC1=CN=CN1 BKAYIFDRRZZKNF-VIFPVBQESA-N 0.000 description 1
- 150000007945 N-acyl ureas Chemical class 0.000 description 1
- 206010052399 Neuroendocrine tumour Diseases 0.000 description 1
- 206010029333 Neurosis Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IQPZOVAOFOKTPD-UHFFFAOYSA-N OC1=CC=C(C=C1)C1=CN=C2C(=N1)N(C(N2)=O)C(C)C2=CC=CC=C2 Chemical compound OC1=CC=C(C=C1)C1=CN=C2C(=N1)N(C(N2)=O)C(C)C2=CC=CC=C2 IQPZOVAOFOKTPD-UHFFFAOYSA-N 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 108700020796 Oncogene Proteins 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 206010033645 Pancreatitis Diseases 0.000 description 1
- 206010033647 Pancreatitis acute Diseases 0.000 description 1
- 206010033649 Pancreatitis chronic Diseases 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 206010073144 Peripheral primitive neuroectodermal tumour of soft tissue Diseases 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 102100022807 Potassium voltage-gated channel subfamily H member 2 Human genes 0.000 description 1
- 206010057846 Primitive neuroectodermal tumour Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 108700020978 Proto-Oncogene Proteins 0.000 description 1
- 102000052575 Proto-Oncogene Human genes 0.000 description 1
- 108010018070 Proto-Oncogene Proteins c-ets Proteins 0.000 description 1
- 102000004053 Proto-Oncogene Proteins c-ets Human genes 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 101710088998 Response regulator inhibitor for tor operon Proteins 0.000 description 1
- 238000011579 SCID mouse model Methods 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 101710142052 Serine/threonine-protein kinase mTOR Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 108020004459 Small interfering RNA Proteins 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-AKLPVKDBSA-N Sulfur-35 Chemical compound [35S] NINIDFKCEFEMDL-AKLPVKDBSA-N 0.000 description 1
- 239000008051 TBE buffer Substances 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- CBPNZQVSJQDFBE-FUXHJELOSA-N Temsirolimus Chemical compound C1C[C@@H](OC(=O)C(C)(CO)CO)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 CBPNZQVSJQDFBE-FUXHJELOSA-N 0.000 description 1
- 238000008050 Total Bilirubin Reagent Methods 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 239000013504 Triton X-100 Substances 0.000 description 1
- 229920004890 Triton X-100 Polymers 0.000 description 1
- 108700025716 Tumor Suppressor Genes Proteins 0.000 description 1
- 102000044209 Tumor Suppressor Genes Human genes 0.000 description 1
- 229940127538 Vascular Endothelial Growth Factor Receptor Inhibitors Drugs 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- PNDPGZBMCMUPRI-XXSWNUTMSA-N [125I][125I] Chemical compound [125I][125I] PNDPGZBMCMUPRI-XXSWNUTMSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 201000003229 acute pancreatitis Diseases 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- IAJILQKETJEXLJ-RSJOWCBRSA-N aldehydo-D-galacturonic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-RSJOWCBRSA-N 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 229940063655 aluminum stearate Drugs 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-M anthranilate Chemical compound NC1=CC=CC=C1C([O-])=O RWZYAGGXGHYGMB-UHFFFAOYSA-M 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 235000015197 apple juice Nutrition 0.000 description 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- 125000002393 azetidinyl group Chemical group 0.000 description 1
- 125000004069 aziridinyl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000004663 bisphosphonates Chemical class 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 235000001465 calcium Nutrition 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- FNAQSUUGMSOBHW-UHFFFAOYSA-H calcium citrate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O FNAQSUUGMSOBHW-UHFFFAOYSA-H 0.000 description 1
- 239000001354 calcium citrate Substances 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 230000021164 cell adhesion Effects 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000006369 cell cycle progression Effects 0.000 description 1
- 230000030833 cell death Effects 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000004709 cell invasion Effects 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 210000003679 cervix uteri Anatomy 0.000 description 1
- CBQPVWSEQWAVRJ-UHFFFAOYSA-N chembl1945495 Chemical compound C1=CC(O)=CC=C1C1=CN=C(NC(=O)N2CC3CCCCC3)C2=N1 CBQPVWSEQWAVRJ-UHFFFAOYSA-N 0.000 description 1
- YLSGPZCOKJCDKJ-UHFFFAOYSA-N chembl1945496 Chemical compound C=1N=C2NC(=O)N(C(C)C)C2=NC=1C1=CC=C(O)C=C1 YLSGPZCOKJCDKJ-UHFFFAOYSA-N 0.000 description 1
- HNDNYBMXRPPOJM-UHFFFAOYSA-N chembl1945787 Chemical compound C=1N=C2NC(=O)N(CCOC)C2=NC=1C1=CC=C(O)C=C1 HNDNYBMXRPPOJM-UHFFFAOYSA-N 0.000 description 1
- 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
- 235000013330 chicken meat Nutrition 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- VDANGULDQQJODZ-UHFFFAOYSA-N chloroprocaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1Cl VDANGULDQQJODZ-UHFFFAOYSA-N 0.000 description 1
- 229960002023 chloroprocaine Drugs 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 230000002759 chromosomal effect Effects 0.000 description 1
- 208000037976 chronic inflammation Diseases 0.000 description 1
- 208000037893 chronic inflammatory disorder Diseases 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000003021 clonogenic effect Effects 0.000 description 1
- 231100000170 comet assay Toxicity 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000011443 conventional therapy Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 229940109239 creatinine Drugs 0.000 description 1
- 108010073357 cyanoginosin LR Proteins 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000004367 cycloalkylaryl group Chemical group 0.000 description 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
- 125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000002380 cytological effect Effects 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- 125000005433 dihydrobenzodioxinyl group Chemical group O1C(COC2=C1C=CC=C2)* 0.000 description 1
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 description 1
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 1
- 238000007907 direct compression Methods 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000007876 drug discovery Methods 0.000 description 1
- 239000003596 drug target Substances 0.000 description 1
- 238000007908 dry granulation Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000008482 dysregulation Effects 0.000 description 1
- 230000005014 ectopic expression Effects 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 229940012017 ethylenediamine Drugs 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000002376 fluorescence recovery after photobleaching Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000001046 green dye Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- 229920000591 gum Polymers 0.000 description 1
- 235000015220 hamburgers Nutrition 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 208000002672 hepatitis B Diseases 0.000 description 1
- 208000010710 hepatitis C virus infection Diseases 0.000 description 1
- 125000005844 heterocyclyloxy group Chemical group 0.000 description 1
- 231100000171 higher toxicity Toxicity 0.000 description 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 1
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- 239000001341 hydroxy propyl starch Substances 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 235000013828 hydroxypropyl starch Nutrition 0.000 description 1
- 239000012216 imaging agent Substances 0.000 description 1
- JXXWJMUPNZDILL-UHFFFAOYSA-N imidazo[4,5-b]pyridin-2-one Chemical compound C1=CC=NC2=NC(=O)N=C21 JXXWJMUPNZDILL-UHFFFAOYSA-N 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011503 in vivo imaging Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229940044173 iodine-125 Drugs 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229960003299 ketamine Drugs 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229960000448 lactic acid Drugs 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 229940124302 mTOR inhibitor Drugs 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098895 maleic acid Drugs 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229940099690 malic acid Drugs 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 208000021644 malignant soft tissue neoplasm Diseases 0.000 description 1
- 239000003628 mammalian target of rapamycin inhibitor Substances 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 108010082117 matrigel Proteins 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 229960003194 meglumine Drugs 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 230000009401 metastasis Effects 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
- LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- ZYZCGGRZINLQBL-GWRQVWKTSA-N microcystin-LR Chemical compound C([C@H](OC)[C@@H](C)\C=C(/C)\C=C\[C@H]1[C@@H](C(=O)N[C@H](CCC(=O)N(C)C(=C)C(=O)N[C@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H]([C@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1)C(O)=O)C(O)=O)C)C1=CC=CC=C1 ZYZCGGRZINLQBL-GWRQVWKTSA-N 0.000 description 1
- DIDLWIPCWUSYPF-UHFFFAOYSA-N microcystin-LR Natural products COC(Cc1ccccc1)C(C)C=C(/C)C=CC2NC(=O)C(NC(CCCNC(=N)N)C(=O)O)NC(=O)C(C)C(NC(=O)C(NC(CC(C)C)C(=O)O)NC(=O)C(C)NC(=O)C(=C)N(C)C(=O)CCC(NC(=O)C2C)C(=O)O)C(=O)O DIDLWIPCWUSYPF-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- BBMQXKKIXBUFQV-UHFFFAOYSA-N n,n-dimethyl-8-oxo-9-phenyl-2-pyridin-3-yl-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)N(C)C)=NC(C=3C=NC=CC=3)=NC=2N1C1=CC=CC=C1 BBMQXKKIXBUFQV-UHFFFAOYSA-N 0.000 description 1
- 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
- GZVYFKDVVRDWRO-UHFFFAOYSA-N n-methyl-8-oxo-9-phenyl-2-pyridin-3-yl-7h-purine-6-carboxamide Chemical compound O=C1NC=2C(C(=O)NC)=NC(C=3C=NC=CC=3)=NC=2N1C1=CC=CC=C1 GZVYFKDVVRDWRO-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 208000016065 neuroendocrine neoplasm Diseases 0.000 description 1
- 201000011519 neuroendocrine tumor Diseases 0.000 description 1
- 208000027831 neuroepithelial neoplasm Diseases 0.000 description 1
- 208000015238 neurotic disease Diseases 0.000 description 1
- 210000000440 neutrophil Anatomy 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 231100000590 oncogenic Toxicity 0.000 description 1
- 230000002246 oncogenic effect Effects 0.000 description 1
- 235000015205 orange juice Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 150000002921 oxetanes Chemical class 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 229940055726 pantothenic acid Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 238000009520 phase I clinical trial Methods 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 238000011518 platinum-based chemotherapy Methods 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 229920003124 powdered cellulose Polymers 0.000 description 1
- 235000019814 powdered cellulose Nutrition 0.000 description 1
- 239000012254 powdered material Substances 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 238000009597 pregnancy test Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000004393 prognosis Methods 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 108010043671 prostatic acid phosphatase Proteins 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical group OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000022983 regulation of cell cycle Effects 0.000 description 1
- 230000016515 regulation of signal transduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 231100000279 safety data Toxicity 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000010206 sensitivity analysis Methods 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 201000008261 skin carcinoma Diseases 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229960003885 sodium benzoate Drugs 0.000 description 1
- 229910001467 sodium calcium phosphate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010268 sodium methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 201000004059 subependymal giant cell astrocytoma Diseases 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000009747 swallowing Effects 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000007885 tablet disintegrant Substances 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 229960000235 temsirolimus Drugs 0.000 description 1
- QFJCIRLUMZQUOT-UHFFFAOYSA-N temsirolimus Natural products C1CC(O)C(OC)CC1CC(C)C1OC(=O)C2CCCCN2C(=O)C(=O)C(O)(O2)C(C)CCC2CC(OC)C(C)=CC=CC=CC(C)CC(C)C(=O)C(OC)C(O)C(C)=CC(C)C(=O)C1 QFJCIRLUMZQUOT-UHFFFAOYSA-N 0.000 description 1
- 125000005944 tetrahydroimidazopyridyl group Chemical group 0.000 description 1
- 125000005888 tetrahydroindolyl group Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 210000000779 thoracic wall Anatomy 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 235000013337 tricalcium citrate Nutrition 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 230000005748 tumor development Effects 0.000 description 1
- 230000002100 tumorsuppressive effect Effects 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- BPICBUSOMSTKRF-UHFFFAOYSA-N xylazine Chemical compound CC1=CC=CC(C)=C1NC1=NCCCS1 BPICBUSOMSTKRF-UHFFFAOYSA-N 0.000 description 1
- 229960001600 xylazine Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
- A61K31/522—Purines, e.g. adenine having oxo groups directly attached to the heterocyclic ring, e.g. hypoxanthine, guanine, acyclovir
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/574—Immunoassay; Biospecific binding assay; Materials therefor for cancer
- G01N33/57407—Specifically defined cancers
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Hematology (AREA)
- Physical Education & Sports Medicine (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Oncology (AREA)
- Cell Biology (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Hospice & Palliative Care (AREA)
- Food Science & Technology (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261611370P | 2012-03-15 | 2012-03-15 | |
| US61/611,370 | 2012-03-15 | ||
| US201261715329P | 2012-10-18 | 2012-10-18 | |
| US61/715,329 | 2012-10-18 | ||
| PCT/US2013/031202 WO2013138556A1 (en) | 2012-03-15 | 2013-03-14 | Treatment of cancer with tor kinase inhibitors |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020197014135A Division KR20190058673A (ko) | 2012-03-15 | 2013-03-14 | Tor 키나제 억제제를 사용한 암의 치료 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20200034818A true KR20200034818A (ko) | 2020-03-31 |
Family
ID=47998542
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020207008188A Ceased KR20200034818A (ko) | 2012-03-15 | 2013-03-14 | Tor 키나제 억제제를 사용한 암의 치료 |
| KR1020147028710A Active KR102057358B1 (ko) | 2012-03-15 | 2013-03-14 | Tor 키나제 억제제를 사용한 암의 치료 |
| KR1020197014135A Ceased KR20190058673A (ko) | 2012-03-15 | 2013-03-14 | Tor 키나제 억제제를 사용한 암의 치료 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020147028710A Active KR102057358B1 (ko) | 2012-03-15 | 2013-03-14 | Tor 키나제 억제제를 사용한 암의 치료 |
| KR1020197014135A Ceased KR20190058673A (ko) | 2012-03-15 | 2013-03-14 | Tor 키나제 억제제를 사용한 암의 치료 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US20130245029A1 (enExample) |
| EP (1) | EP2825168B1 (enExample) |
| JP (2) | JP2015516375A (enExample) |
| KR (3) | KR20200034818A (enExample) |
| CN (2) | CN107137402A (enExample) |
| AU (1) | AU2013203156C1 (enExample) |
| BR (1) | BR112014022697A2 (enExample) |
| CA (1) | CA2867349A1 (enExample) |
| EA (1) | EA028434B1 (enExample) |
| ES (1) | ES2677908T3 (enExample) |
| IL (2) | IL234640B (enExample) |
| MX (1) | MX360877B (enExample) |
| MY (1) | MY182650A (enExample) |
| NI (1) | NI201400109A (enExample) |
| NZ (1) | NZ628421A (enExample) |
| PH (2) | PH12014502048B1 (enExample) |
| SG (1) | SG11201405706TA (enExample) |
| TW (2) | TWI600428B (enExample) |
| WO (1) | WO2013138556A1 (enExample) |
| ZA (1) | ZA201406709B (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2013203714B2 (en) | 2012-10-18 | 2015-12-03 | Signal Pharmaceuticals, Llc | Inhibition of phosphorylation of PRAS40, GSK3-beta or P70S6K1 as a marker for TOR kinase inhibitory activity |
| EP2945636B1 (en) | 2013-01-16 | 2017-06-28 | Signal Pharmaceuticals, LLC | Substituted pyrrolopyrimidine compounds, compositions thereof, and methods of treatment therewith |
| BR112015026257B1 (pt) | 2013-04-17 | 2022-12-20 | Signal Pharmaceuticals, Llc | Uso de um composto dihidropirazino-pirazina e enzalutamida, composição farmacêutica que os compreende, e kit |
| SG11201508527VA (en) | 2013-04-17 | 2015-11-27 | Signal Pharm Llc | Pharmaceutical formulations, processes, solid forms and methods of use relating to 1-ethyl-7-(2-methyl-6-(1h-1,2,4-triazol-3-yl) pyridin-3-yl) -3,4-dihydropyrazino[2,3-b]pyrazin-2(1h)-one |
| ES2944478T3 (es) | 2013-04-17 | 2023-06-21 | Signal Pharm Llc | 1-etil-7-(2-metil-6-(1H-1,2,4-triazol-3-il)piridin-3-il)-3,4-dihidropirazino[2,3-b]pirazin-2(1H)-ona para tratar el glioblastoma multiforme |
| NZ629411A (en) | 2013-04-17 | 2017-06-30 | Signal Pharm Llc | Treatment of cancer with dihydropyrazino-pyrazines |
| AU2014254057A1 (en) | 2013-04-17 | 2015-11-05 | Signal Pharmaceuticals, Llc | Combination therapy comprising a TOR kinase inhibitor and N-(3-(5-fluoro-2-(4-(2-methoxyethoxy)phenylamino)pyrimidin-4-ylamino)phenyl)acrylamide for treating cancer |
| MX368286B (es) | 2013-04-17 | 2019-09-27 | Signal Pharm Llc | Terapia de combinacion que comprende un inhibidor de tor cinasa y un compuesto de quinazolinona 5-sustituida para tratar cancer. |
| KR102242505B1 (ko) | 2013-04-17 | 2021-04-20 | 시그날 파마소티칼 엘엘씨 | 암 치료용 tor 키나제 억제제 및 시티딘 유사체를 포함하는 병용 요법 |
| JP6401250B2 (ja) | 2013-05-29 | 2018-10-10 | シグナル ファーマシューティカルズ，エルエルシー | ７−（６−（２−ヒドロキシプロパン−２−イル）ピリジン−３−イル）−１−（（ｔｒａｎｓ）−４−メトキシシクロヘキシル）−３，４−ジヒドロピラジノ［２，３−ｂ］ピラジン−２（１Ｈ）−オン、その固体形態の医薬組成物、及びその使用方法 |
| NZ714742A (en) | 2014-04-16 | 2017-04-28 | Signal Pharm Llc | Solid forms of 1-ethyl-7-(2-methyl-6-(1h-1,2,4-triazol-3-yl)pyridin-3-yl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1h)-one, compositions thereof and methods of their use |
| US9718824B2 (en) | 2014-04-16 | 2017-08-01 | Signal Pharmaceuticals, Llc | Solid forms comprising 7-(6-(2-hydroxypropan-2-yl)pyridin-3-yl)-1-((trans)-4-methoxycyclohexyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one, and a coformer, compositions and methods of use thereof |
| US9737535B2 (en) | 2014-04-16 | 2017-08-22 | Signal Pharmaceuticals, Llc | Methods for treating cancer using TOR kinase inhibitor combination therapy comprising administering substituted pyrazino[2,3-b]pyrazines |
| US9512129B2 (en) | 2014-04-16 | 2016-12-06 | Signal Pharmaceuticals, Llc | Solid forms comprising 1-ethyl-7-(2-methyl-6-(1H-1,2,4-triazol-3-yl)pyridin-3-yl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one and a coformer |
| AU2015289929A1 (en) | 2014-07-14 | 2017-03-02 | Signal Pharmaceuticals, Llc | Methods of treating a cancer using substituted pyrrolopyrimidine compounds, compositions thereof |
| NZ629796A (en) | 2014-07-14 | 2015-12-24 | Signal Pharm Llc | Amorphous form of 4-((4-(cyclopentyloxy)-5-(2-methylbenzo[d]oxazol-6-yl)-7h-pyrrolo[2,3-d]pyrimidin-2-yl)amino)-3-methoxy-n-methylbenzamide, compositions thereof and methods of their use |
| HUE054548T2 (hu) * | 2016-12-20 | 2021-09-28 | Astrazeneca Ab | Amino-triazolopiridin vegyületek és azok alkalmazása rák kezelésében |
| EP3641772B1 (en) | 2017-06-22 | 2023-08-02 | Celgene Corporation | Treatment of hepatocellular carcinoma characterized by hepatitis b virus infection |
| JP7466450B2 (ja) | 2018-03-01 | 2024-04-12 | エシロール・アンテルナシオナル | レンズ要素 |
| CN113493471B (zh) * | 2020-04-03 | 2024-06-11 | 山东轩竹医药科技有限公司 | 杂芳环类激酶抑制剂 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2383370T3 (es) | 2006-10-19 | 2012-06-20 | Signal Pharmaceuticals Llc | Compuestos de heteroarilo, sus composiciones y uso de los mismos como inhibidores de proteína quinasa |
| EP2457913B1 (en) * | 2006-10-19 | 2017-04-19 | Signal Pharmaceuticals, LLC | Heteroaryl compounds, compositions thereof, and methods of treatment therewith |
| US8110578B2 (en) * | 2008-10-27 | 2012-02-07 | Signal Pharmaceuticals, Llc | Pyrazino[2,3-b]pyrazine mTOR kinase inhibitors for oncology indications and diseases associated with the mTOR/PI3K/Akt pathway |
| JP2013508456A (ja) | 2009-10-26 | 2013-03-07 | シグナル ファーマシューティカルズ， エルエルシー | ヘテロアリール化合物の合成方法および精製方法 |
| WO2011133668A2 (en) * | 2010-04-20 | 2011-10-27 | President And Fellows Of Harvard College | Methods and compositions for the treatment of cancer |
-
2013
- 2013-03-14 KR KR1020207008188A patent/KR20200034818A/ko not_active Ceased
- 2013-03-14 EP EP13712647.0A patent/EP2825168B1/en active Active
- 2013-03-14 JP JP2015500595A patent/JP2015516375A/ja active Pending
- 2013-03-14 US US13/803,323 patent/US20130245029A1/en not_active Abandoned
- 2013-03-14 MY MYPI2014702606A patent/MY182650A/en unknown
- 2013-03-14 ES ES13712647.0T patent/ES2677908T3/es active Active
- 2013-03-14 TW TW102109153A patent/TWI600428B/zh active
- 2013-03-14 KR KR1020147028710A patent/KR102057358B1/ko active Active
- 2013-03-14 CN CN201710422322.9A patent/CN107137402A/zh active Pending
- 2013-03-14 CA CA2867349A patent/CA2867349A1/en not_active Abandoned
- 2013-03-14 MX MX2014011117A patent/MX360877B/es active IP Right Grant
- 2013-03-14 TW TW106122809A patent/TWI664968B/zh active
- 2013-03-14 AU AU2013203156A patent/AU2013203156C1/en not_active Ceased
- 2013-03-14 SG SG11201405706TA patent/SG11201405706TA/en unknown
- 2013-03-14 WO PCT/US2013/031202 patent/WO2013138556A1/en not_active Ceased
- 2013-03-14 KR KR1020197014135A patent/KR20190058673A/ko not_active Ceased
- 2013-03-14 BR BR112014022697-0A patent/BR112014022697A2/pt not_active Application Discontinuation
- 2013-03-14 CN CN201380025102.2A patent/CN104302295B/zh active Active
- 2013-03-14 EA EA201491694A patent/EA028434B1/ru not_active IP Right Cessation
- 2013-03-14 NZ NZ628421A patent/NZ628421A/en not_active IP Right Cessation
-
2014
- 2014-09-12 ZA ZA2014/06709A patent/ZA201406709B/en unknown
- 2014-09-12 NI NI201400109A patent/NI201400109A/es unknown
- 2014-09-14 IL IL234640A patent/IL234640B/en active IP Right Grant
- 2014-09-15 PH PH12014502048A patent/PH12014502048B1/en unknown
-
2017
- 2017-11-13 JP JP2017218364A patent/JP6470821B2/ja active Active
-
2018
- 2018-10-18 PH PH12018502234A patent/PH12018502234B1/en unknown
-
2020
- 2020-04-28 IL IL274318A patent/IL274318A/en unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR102057358B1 (ko) | Tor 키나제 억제제를 사용한 암의 치료 | |
| KR102057357B1 (ko) | Tor 키나제 억제제를 사용한 암의 치료 | |
| KR102122617B1 (ko) | Tor 키나제 억제자를 사용하는 암의 치료 | |
| KR102057359B1 (ko) | Tor 키나아제 억제제를 사용하는 암 치료법 | |
| KR102157914B1 (ko) | Tor 키나제 억제제를 사용한 전립선암의 치료 | |
| HK1239543A1 (en) | Treatment of cancer with tor kinase inhibitors | |
| HK1201755B (en) | Treatment of cancer with tor kinase inhibitors | |
| HK1202247B (en) | Treatment of cancer with tor kinase inhibitors | |
| HK1201750B (en) | Treatment of cancer with tor kinase inhibitors |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A107 | Divisional application of patent | ||
| PA0104 | Divisional application for international application |
Comment text: Divisional Application for International Patent Patent event code: PA01041R01D Patent event date: 20200320 Application number text: 1020197014135 Filing date: 20190516 |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20200406 Comment text: Request for Examination of Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20200424 Patent event code: PE09021S01D |
|
| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent |
Patent event date: 20220804 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 20200424 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |