CA2520251A1

CA2520251A1 - Substituted 4-amino[1,2,4]triazolo[4,3-a]quinoxalines

Substituted 4-amino[1,2,4]triazolo[4,3-a]quinoxalines Download PDF

Info

Publication number: CA2520251A1
Authority: CA; Canada
Prior art keywords: triazolo; quinoxaline; fluoro; ylamino; ethylamino
Prior art date: 2003-03-27
Legal status : Abandoned

Application number

CA002520251A

Other languages

English (en)

French (fr)

Inventor

John William Benbow

Margaret Yuhua Chu-Moyer

Daniel Wei-Shung Kung

Current Assignee

Pfizer Products Inc

Original Assignee

Individual

Priority date

2003-03-27

Filing date

2004-03-15

Publication date

2004-10-07

2004-03-15 Application filed by Individual filed Critical Individual

2004-10-07 Publication of CA2520251A1 publication Critical patent/CA2520251A1/en

Status Abandoned legal-status Critical Current

Links

JQHGLMJLABTXOL-UHFFFAOYSA-N [1,2,4]triazolo[4,3-a]quinoxalin-4-amine Chemical class NC1=NC2=CC=CC=C2N2C1=NN=C2 JQHGLMJLABTXOL-UHFFFAOYSA-N 0.000 title abstract description 3
150000001875 compounds Chemical class 0.000 claims abstract description 128
239000000203 mixture Substances 0.000 claims abstract description 74
239000000651 prodrug Substances 0.000 claims abstract description 48
229940002612 prodrug Drugs 0.000 claims abstract description 48
150000003839 salts Chemical class 0.000 claims abstract description 27
108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 claims abstract description 24
239000003112 inhibitor Substances 0.000 claims abstract description 21
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 16
201000010099 disease Diseases 0.000 claims abstract description 13
206010012601 diabetes mellitus Diseases 0.000 claims abstract description 10
208000024891 symptom Diseases 0.000 claims abstract description 10
201000004384 Alopecia Diseases 0.000 claims abstract description 6
208000020925 Bipolar disease Diseases 0.000 claims abstract description 6
206010028980 Neoplasm Diseases 0.000 claims abstract description 6
201000011510 cancer Diseases 0.000 claims abstract description 6
208000024963 hair loss Diseases 0.000 claims abstract description 6
230000003676 hair loss Effects 0.000 claims abstract description 6
206010012289 Dementia Diseases 0.000 claims abstract description 5
208000006011 Stroke Diseases 0.000 claims abstract description 5
201000000980 schizophrenia Diseases 0.000 claims abstract description 5
238000000034 method Methods 0.000 claims description 39
229910052739 hydrogen Inorganic materials 0.000 claims description 35
239000001257 hydrogen Substances 0.000 claims description 35
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 34
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 28
125000001072 heteroaryl group Chemical group 0.000 claims description 27
125000003118 aryl group Chemical group 0.000 claims description 22
229910052736 halogen Inorganic materials 0.000 claims description 20
150000002367 halogens Chemical class 0.000 claims description 20
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
125000000753 cycloalkyl group Chemical group 0.000 claims description 13
239000008194 pharmaceutical composition Substances 0.000 claims description 13
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
241000124008 Mammalia Species 0.000 claims description 11
230000000694 effects Effects 0.000 claims description 11
230000002401 inhibitory effect Effects 0.000 claims description 11
125000004093 cyano group Chemical group *C#N 0.000 claims description 10
239000003085 diluting agent Substances 0.000 claims description 10
239000003981 vehicle Substances 0.000 claims description 10
239000003795 chemical substances by application Substances 0.000 claims description 9
125000005842 heteroatom Chemical group 0.000 claims description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
239000003937 drug carrier Substances 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 7
229940124834 selective serotonin reuptake inhibitor Drugs 0.000 claims description 7
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ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical group O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
229940044551 receptor antagonist Drugs 0.000 claims description 6
239000002464 receptor antagonist Substances 0.000 claims description 6
208000024827 Alzheimer disease Diseases 0.000 claims description 5
102000001301 EGF receptor Human genes 0.000 claims description 5
108060006698 EGF receptor Proteins 0.000 claims description 5
102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 claims description 5
101710100968 Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 claims description 5
102000003978 Tissue Plasminogen Activator Human genes 0.000 claims description 5
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239000004037 angiogenesis inhibitor Substances 0.000 claims description 5
239000000164 antipsychotic agent Substances 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
239000000544 cholinesterase inhibitor Substances 0.000 claims description 5
125000001153 fluoro group Chemical group F* 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
230000019491 signal transduction Effects 0.000 claims description 5
159000000000 sodium salts Chemical class 0.000 claims description 5
229960000187 tissue plasminogen activator Drugs 0.000 claims description 5
125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 4
229940100578 Acetylcholinesterase inhibitor Drugs 0.000 claims description 4
206010061218 Inflammation Diseases 0.000 claims description 4
208000019022 Mood disease Diseases 0.000 claims description 4
208000008589 Obesity Diseases 0.000 claims description 4
102000004257 Potassium Channel Human genes 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
230000001028 anti-proliverative effect Effects 0.000 claims description 4
208000006673 asthma Diseases 0.000 claims description 4
230000004054 inflammatory process Effects 0.000 claims description 4
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125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
230000016273 neuron death Effects 0.000 claims description 4
235000020824 obesity Nutrition 0.000 claims description 4
108020001213 potassium channel Proteins 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
208000011580 syndromic disease Diseases 0.000 claims description 4
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206010019280 Heart failures Diseases 0.000 claims description 3
208000031226 Hyperlipidaemia Diseases 0.000 claims description 3
208000013016 Hypoglycemia Diseases 0.000 claims description 3
102000002002 Neurokinin-1 Receptors Human genes 0.000 claims description 3
108010040718 Neurokinin-1 Receptors Proteins 0.000 claims description 3
208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 3
206010036049 Polycystic ovaries Diseases 0.000 claims description 3
XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 claims description 3
208000030886 Traumatic Brain injury Diseases 0.000 claims description 3
230000036506 anxiety Effects 0.000 claims description 3
125000001246 bromo group Chemical group Br* 0.000 claims description 3
208000035475 disorder Diseases 0.000 claims description 3
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201000001421 hyperglycemia Diseases 0.000 claims description 3
230000002218 hypoglycaemic effect Effects 0.000 claims description 3
208000028867 ischemia Diseases 0.000 claims description 3
230000001404 mediated effect Effects 0.000 claims description 3
201000010065 polycystic ovary syndrome Diseases 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
230000019100 sperm motility Effects 0.000 claims description 3
230000009529 traumatic brain injury Effects 0.000 claims description 3
239000002525 vasculotropin inhibitor Substances 0.000 claims description 3
MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical group C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 claims description 3
AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 claims description 2
RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 claims description 2
PXZMKEFFLJITPC-UHFFFAOYSA-N 1-oxo-4-(propan-2-ylamino)-2h-[1,2,4]triazolo[4,3-a]quinoxaline-8-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2N3C(=O)NN=C3C(NC(C)C)=NC2=C1 PXZMKEFFLJITPC-UHFFFAOYSA-N 0.000 claims description 2
UQZWDYHEEVPFDP-UHFFFAOYSA-N 8-fluoro-4-[2-[[5-(trifluoromethyl)pyridin-2-yl]amino]ethylamino]-2h-[1,2,4]triazolo[4,3-a]quinoxalin-1-one Chemical compound C12=NNC(=O)N2C2=CC(F)=CC=C2N=C1NCCNC1=CC=C(C(F)(F)F)C=N1 UQZWDYHEEVPFDP-UHFFFAOYSA-N 0.000 claims description 2
AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 claims description 2
PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Natural products C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-UHFFFAOYSA-N 0.000 claims description 2
SNPPWIUOZRMYNY-UHFFFAOYSA-N bupropion Chemical compound CC(C)(C)NC(C)C(=O)C1=CC=CC(Cl)=C1 SNPPWIUOZRMYNY-UHFFFAOYSA-N 0.000 claims description 2
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 2
229960000590 celecoxib Drugs 0.000 claims description 2
RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 claims description 2
229960003530 donepezil Drugs 0.000 claims description 2
229960002464 fluoxetine Drugs 0.000 claims description 2
229960004038 fluvoxamine Drugs 0.000 claims description 2
CJOFXWAVKWHTFT-XSFVSMFZSA-N fluvoxamine Chemical compound COCCCC\C(=N/OCCN)C1=CC=C(C(F)(F)F)C=C1 CJOFXWAVKWHTFT-XSFVSMFZSA-N 0.000 claims description 2
229960000647 gepirone Drugs 0.000 claims description 2
QOIGKGMMAGJZNZ-UHFFFAOYSA-N gepirone Chemical compound O=C1CC(C)(C)CC(=O)N1CCCCN1CCN(C=2N=CC=CN=2)CC1 QOIGKGMMAGJZNZ-UHFFFAOYSA-N 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
229960001952 metrifonate Drugs 0.000 claims description 2
MNPWTSPVEBLRLC-UHFFFAOYSA-N n-(2-methoxyethyl)-n-methyl-1-oxo-4-(propan-2-ylamino)-2h-[1,2,4]triazolo[4,3-a]quinoxaline-7-carboxamide Chemical compound N1=C(NC(C)C)C2=NNC(=O)N2C2=CC=C(C(=O)N(C)CCOC)C=C21 MNPWTSPVEBLRLC-UHFFFAOYSA-N 0.000 claims description 2
210000000440 neutrophil Anatomy 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 claims description 2
229960005017 olanzapine Drugs 0.000 claims description 2
229960002296 paroxetine Drugs 0.000 claims description 2
PIJVFDBKTWXHHD-HIFRSBDPSA-N physostigmine Chemical compound C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C PIJVFDBKTWXHHD-HIFRSBDPSA-N 0.000 claims description 2
229960001697 physostigmine Drugs 0.000 claims description 2
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229960001534 risperidone Drugs 0.000 claims description 2
RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 claims description 2
229960004136 rivastigmine Drugs 0.000 claims description 2
RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 claims description 2
229960000371 rofecoxib Drugs 0.000 claims description 2
229960002073 sertraline Drugs 0.000 claims description 2
VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 claims description 2
WNUQCGWXPNGORO-NRFANRHFSA-N sonepiprazole Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1CCN(CC[C@H]2C3=CC=CC=C3CCO2)CC1 WNUQCGWXPNGORO-NRFANRHFSA-N 0.000 claims description 2
229950001013 sonepiprazole Drugs 0.000 claims description 2
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NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 claims description 2
LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 claims description 2
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102000001267 GSK3 Human genes 0.000 claims 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
KFXAGPAFAZACTF-UHFFFAOYSA-N 2-[2-[(8-fluoro-1-oxo-2h-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl)amino]ethylamino]pyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC(NCCNC=2C=3N(C(NN=3)=O)C3=CC(F)=CC=C3N=2)=C1 KFXAGPAFAZACTF-UHFFFAOYSA-N 0.000 claims 1
ZUTGWLVWEXAZFZ-UHFFFAOYSA-N 4-(cyclohexylamino)-8-fluoro-2h-[1,2,4]triazolo[4,3-a]quinoxalin-1-one Chemical compound C12=NNC(=O)N2C2=CC(F)=CC=C2N=C1NC1CCCCC1 ZUTGWLVWEXAZFZ-UHFFFAOYSA-N 0.000 claims 1
GCTIPTOILDRCTQ-UHFFFAOYSA-N 4-[2-(1,3-benzothiazol-2-ylamino)ethylamino]-8-bromo-2h-[1,2,4]triazolo[4,3-a]quinoxalin-1-one Chemical compound C1=CC=C2SC(NCCNC3=NC4=CC=C(C=C4N4C(=O)NN=C43)Br)=NC2=C1 GCTIPTOILDRCTQ-UHFFFAOYSA-N 0.000 claims 1
DQLKJLTVCGYPMN-UHFFFAOYSA-N 4-[2-(1,3-benzothiazol-2-ylamino)ethylamino]-8-chloro-2h-[1,2,4]triazolo[4,3-a]quinoxalin-1-one Chemical compound C1=CC=C2SC(NCCNC3=NC4=CC=C(C=C4N4C(=O)NN=C43)Cl)=NC2=C1 DQLKJLTVCGYPMN-UHFFFAOYSA-N 0.000 claims 1
DTCPCLVJEXZDMV-UHFFFAOYSA-N 4-[2-(1,3-benzothiazol-2-ylamino)ethylamino]-8-fluoro-2h-[1,2,4]triazolo[4,3-a]quinoxalin-1-one Chemical compound C1=CC=C2SC(NCCNC3=NC4=CC=C(C=C4N4C(=O)NN=C43)F)=NC2=C1 DTCPCLVJEXZDMV-UHFFFAOYSA-N 0.000 claims 1
XWHQYWHAGZHMTP-UHFFFAOYSA-N 4-[2-(1,3-benzoxazol-2-ylamino)ethylamino]-8-chloro-2h-[1,2,4]triazolo[4,3-a]quinoxalin-1-one Chemical compound C1=CC=C2OC(NCCNC3=NC4=CC=C(C=C4N4C(=O)NN=C43)Cl)=NC2=C1 XWHQYWHAGZHMTP-UHFFFAOYSA-N 0.000 claims 1
WQEHXWXAQIXUGH-UHFFFAOYSA-N 4-[2-(1h-benzimidazol-2-yl)butylamino]-8-fluoro-2h-[1,2,4]triazolo[4,3-a]quinoxalin-1-one Chemical compound C1=CC=C2NC(C(CNC=3C=4N(C(NN=4)=O)C4=CC(F)=CC=C4N=3)CC)=NC2=C1 WQEHXWXAQIXUGH-UHFFFAOYSA-N 0.000 claims 1
MTSWFWHZXIJPHN-UHFFFAOYSA-N 4-[2-(1h-benzimidazol-2-ylamino)ethylamino]-8-fluoro-2h-[1,2,4]triazolo[4,3-a]quinoxalin-1-one Chemical compound C1=CC=C2NC(NCCNC3=NC4=CC=C(C=C4N4C(=O)NN=C43)F)=NC2=C1 MTSWFWHZXIJPHN-UHFFFAOYSA-N 0.000 claims 1
ZOROJULRSKJKDG-UHFFFAOYSA-N 4-[2-[(6-methoxy-1,3-benzothiazol-2-yl)amino]ethylamino]-2h-[1,2,4]triazolo[4,3-a]quinoxalin-1-one Chemical compound C1=CC=C2N3C(=O)NN=C3C(NCCNC3=NC4=CC=C(C=C4S3)OC)=NC2=C1 ZOROJULRSKJKDG-UHFFFAOYSA-N 0.000 claims 1
VYDTXMSIVVYJGU-UHFFFAOYSA-N 6-[2-[(8-fluoro-1-oxo-2h-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl)amino]ethylamino]pyridine-3-carbonitrile Chemical compound C12=NNC(=O)N2C2=CC(F)=CC=C2N=C1NCCNC1=CC=C(C#N)C=N1 VYDTXMSIVVYJGU-UHFFFAOYSA-N 0.000 claims 1
REOJYBIYCXOOTG-UHFFFAOYSA-N 8-bromo-4-[2-(1h-indol-3-yl)ethylamino]-2h-[1,2,4]triazolo[4,3-a]quinoxalin-1-one Chemical compound C1=CC=C2C(CCNC3=NC4=CC=C(C=C4N4C(=O)NN=C43)Br)=CNC2=C1 REOJYBIYCXOOTG-UHFFFAOYSA-N 0.000 claims 1
XJJIOJZYYCLMTI-UHFFFAOYSA-N 8-chloro-4-(propan-2-ylamino)-2h-[1,2,4]triazolo[4,3-a]quinoxalin-1-one Chemical compound C1=C(Cl)C=C2N3C(=O)NN=C3C(NC(C)C)=NC2=C1 XJJIOJZYYCLMTI-UHFFFAOYSA-N 0.000 claims 1
KWALIVPUAKSPCP-UHFFFAOYSA-N 8-fluoro-4-[2-(1h-indol-3-yl)ethylamino]-2h-[1,2,4]triazolo[4,3-a]quinoxalin-1-one Chemical compound C1=CC=C2C(CCNC3=NC4=CC=C(C=C4N4C(=O)NN=C43)F)=CNC2=C1 KWALIVPUAKSPCP-UHFFFAOYSA-N 0.000 claims 1
YRCPHZWTKSGHSS-UHFFFAOYSA-N 8-fluoro-4-[2-(pyridin-2-ylamino)ethylamino]-2h-[1,2,4]triazolo[4,3-a]quinoxalin-1-one Chemical compound C12=NNC(=O)N2C2=CC(F)=CC=C2N=C1NCCNC1=CC=CC=N1 YRCPHZWTKSGHSS-UHFFFAOYSA-N 0.000 claims 1
MLEFTFDTWUPPDY-UHFFFAOYSA-N 8-fluoro-4-[2-(pyrimidin-2-ylamino)ethylamino]-2h-[1,2,4]triazolo[4,3-a]quinoxalin-1-one Chemical compound C12=NNC(=O)N2C2=CC(F)=CC=C2N=C1NCCNC1=NC=CC=N1 MLEFTFDTWUPPDY-UHFFFAOYSA-N 0.000 claims 1
XVKOTFSLWHIFFH-UHFFFAOYSA-N 8-fluoro-4-[2-(quinolin-2-ylamino)ethylamino]-2h-[1,2,4]triazolo[4,3-a]quinoxalin-1-one Chemical compound C1=CC=CC2=NC(NCCNC3=NC4=CC=C(C=C4N4C(=O)NN=C43)F)=CC=C21 XVKOTFSLWHIFFH-UHFFFAOYSA-N 0.000 claims 1
HMCVHHBRBPYOPP-UHFFFAOYSA-N 8-fluoro-4-[2-[(6-methyl-7,8-dihydro-5h-1,6-naphthyridin-2-yl)amino]ethylamino]-2h-[1,2,4]triazolo[4,3-a]quinoxalin-1-one Chemical compound C1=C(F)C=C2N3C(=O)NN=C3C(NCCNC=3N=C4CCN(CC4=CC=3)C)=NC2=C1 HMCVHHBRBPYOPP-UHFFFAOYSA-N 0.000 claims 1
ANVDTASCIIMUAR-UHFFFAOYSA-N 8-fluoro-4-[2-[[2-(trifluoromethyl)quinolin-4-yl]amino]ethylamino]-2h-[1,2,4]triazolo[4,3-a]quinoxalin-1-one Chemical compound C1=CC=C2C(NCCNC3=NC4=CC=C(C=C4N4C(=O)NN=C43)F)=CC(C(F)(F)F)=NC2=C1 ANVDTASCIIMUAR-UHFFFAOYSA-N 0.000 claims 1
ZIPINCGXMGLYQS-UHFFFAOYSA-N 8-fluoro-4-[2-[[3-(trifluoromethyl)pyridin-2-yl]amino]ethylamino]-2h-[1,2,4]triazolo[4,3-a]quinoxalin-1-one Chemical compound C12=NNC(=O)N2C2=CC(F)=CC=C2N=C1NCCNC1=NC=CC=C1C(F)(F)F ZIPINCGXMGLYQS-UHFFFAOYSA-N 0.000 claims 1
LZZOFKAICDKLAU-UHFFFAOYSA-N 8-fluoro-4-[2-[[4-(morpholin-4-ylmethyl)pyridin-2-yl]amino]ethylamino]-2h-[1,2,4]triazolo[4,3-a]quinoxalin-1-one Chemical compound C12=NNC(=O)N2C2=CC(F)=CC=C2N=C1NCCNC(N=CC=1)=CC=1CN1CCOCC1 LZZOFKAICDKLAU-UHFFFAOYSA-N 0.000 claims 1
FEUUGOAXQVQTAU-UHFFFAOYSA-N 8-fluoro-4-[2-[[4-(trifluoromethyl)pyridin-2-yl]amino]ethylamino]-2h-[1,2,4]triazolo[4,3-a]quinoxalin-1-one Chemical compound C12=NNC(=O)N2C2=CC(F)=CC=C2N=C1NCCNC1=CC(C(F)(F)F)=CC=N1 FEUUGOAXQVQTAU-UHFFFAOYSA-N 0.000 claims 1
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