JP2006521343A5 - - Google Patents
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- Publication number
- JP2006521343A5 JP2006521343A5 JP2006506368A JP2006506368A JP2006521343A5 JP 2006521343 A5 JP2006521343 A5 JP 2006521343A5 JP 2006506368 A JP2006506368 A JP 2006506368A JP 2006506368 A JP2006506368 A JP 2006506368A JP 2006521343 A5 JP2006521343 A5 JP 2006521343A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- triazolo
- quinoxalin
- fluoro
- ylamino
- 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.)
- Withdrawn
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 21
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 239000001257 hydrogen Substances 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 12
- 239000000651 prodrug Substances 0.000 claims 12
- 229940002612 prodrug Drugs 0.000 claims 12
- 125000001072 heteroaryl group Chemical group 0.000 claims 11
- 125000005843 halogen group Chemical group 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 201000010099 disease Diseases 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- -1 -COR 5 Chemical group 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 239000003112 inhibitor Substances 0.000 claims 5
- 208000024891 symptom Diseases 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 206010012601 diabetes mellitus Diseases 0.000 claims 4
- 201000000980 schizophrenia Diseases 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 201000004384 Alopecia Diseases 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- 206010012289 Dementia Diseases 0.000 claims 2
- 208000007530 Essential hypertension Diseases 0.000 claims 2
- 102000001267 GSK3 Human genes 0.000 claims 2
- 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 claims 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 2
- 208000013016 Hypoglycemia Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 208000019022 Mood disease Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 2
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 2
- 230000005856 abnormality Effects 0.000 claims 2
- 231100000360 alopecia Toxicity 0.000 claims 2
- 239000004037 angiogenesis inhibitor Substances 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 239000000544 cholinesterase inhibitor Substances 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 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 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 230000035558 fertility Effects 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 201000001421 hyperglycemia Diseases 0.000 claims 2
- 230000002218 hypoglycaemic effect Effects 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 208000028867 ischemia Diseases 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 230000016273 neuron death Effects 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 230000002611 ovarian Effects 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 claims 2
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 claims 2
- 230000011664 signaling Effects 0.000 claims 2
- 230000019100 sperm motility Effects 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 230000009529 traumatic brain injury Effects 0.000 claims 2
- 230000003313 weakening effect Effects 0.000 claims 2
- 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 1
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims 1
- 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 1
- 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 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
- FOYUJKGHIROOLZ-UHFFFAOYSA-N 4-[2-(1H-benzimidazol-2-yl)propylamino]-8-fluoro-2H-[1,2,4]triazolo[4,3-a]quinoxalin-1-one Chemical compound N1C(=NC2=C1C=CC=C2)C(CNC=1C=2N(C3=CC(=CC=C3N=1)F)C(NN=2)=O)C FOYUJKGHIROOLZ-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
- KKYULXJAUKKHEL-UHFFFAOYSA-N 4-[2-(1h-benzimidazol-2-yl)ethylamino]-8-fluoro-2h-[1,2,4]triazolo[4,3-a]quinoxalin-1-one Chemical compound C1=CC=C2NC(CCNC3=NC4=CC=C(C=C4N4C(=O)NN=C43)F)=NC2=C1 KKYULXJAUKKHEL-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
- KDJDNKRVSXCFMP-UHFFFAOYSA-N 8-bromo-4-(propan-2-ylamino)-2h-[1,2,4]triazolo[4,3-a]quinoxalin-1-one Chemical compound C1=C(Br)C=C2N3C(=O)NN=C3C(NC(C)C)=NC2=C1 KDJDNKRVSXCFMP-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
- BPVGPMPKZVREPE-UHFFFAOYSA-N 8-fluoro-4-(oxan-4-ylamino)-2h-[1,2,4]triazolo[4,3-a]quinoxalin-1-one Chemical compound C12=NNC(=O)N2C2=CC(F)=CC=C2N=C1NC1CCOCC1 BPVGPMPKZVREPE-UHFFFAOYSA-N 0.000 claims 1
- RGVOOFCKJSQMCZ-UHFFFAOYSA-N 8-fluoro-4-(piperidin-4-ylamino)-2h-[1,2,4]triazolo[4,3-a]quinoxalin-1-one Chemical compound C12=NNC(=O)N2C2=CC(F)=CC=C2N=C1NC1CCNCC1 RGVOOFCKJSQMCZ-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
- RZEAENJTKZGXAT-UHFFFAOYSA-N 8-fluoro-4-[2-[[4-(trifluoromethyl)pyrimidin-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(C(F)(F)F)=N1 RZEAENJTKZGXAT-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- SMEIINRASDQSPP-UHFFFAOYSA-N 8-fluoro-4-[2-[[5-(trifluoromethyl)pyridin-2-yl]amino]propylamino]-2h-[1,2,4]triazolo[4,3-a]quinoxalin-1-one Chemical compound N=1C2=CC=C(F)C=C2N(C(NN=2)=O)C=2C=1NCC(C)NC1=CC=C(C(F)(F)F)C=N1 SMEIINRASDQSPP-UHFFFAOYSA-N 0.000 claims 1
- MXOLAIHWSZXTGJ-UHFFFAOYSA-N 8-fluoro-4-[2-[[7-(trifluoromethyl)quinolin-4-yl]amino]ethylamino]-2h-[1,2,4]triazolo[4,3-a]quinoxalin-1-one Chemical compound FC(F)(F)C1=CC=C2C(NCCNC3=NC4=CC=C(C=C4N4C(=O)NN=C43)F)=CC=NC2=C1 MXOLAIHWSZXTGJ-UHFFFAOYSA-N 0.000 claims 1
- YDWXKRYQVHPCAL-UHFFFAOYSA-N 8-fluoro-4-[2-[[8-(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=NC2=C1C(F)(F)F YDWXKRYQVHPCAL-UHFFFAOYSA-N 0.000 claims 1
- OMVLNJOUIXGGHJ-UHFFFAOYSA-N 8-fluoro-4-[3-[[5-(trifluoromethyl)pyridin-2-yl]amino]propylamino]-2h-[1,2,4]triazolo[4,3-a]quinoxalin-1-one Chemical compound C12=NNC(=O)N2C2=CC(F)=CC=C2N=C1NCCCNC1=CC=C(C(F)(F)F)C=N1 OMVLNJOUIXGGHJ-UHFFFAOYSA-N 0.000 claims 1
- LNQISVURZIFKIP-UHFFFAOYSA-N 8-fluoro-4-propan-2-yl-2h-[1,2,4]triazolo[4,3-a]quinoxalin-1-one Chemical compound C1=C(F)C=C2N3C(=O)NN=C3C(C(C)C)=NC2=C1 LNQISVURZIFKIP-UHFFFAOYSA-N 0.000 claims 1
- 229940100578 Acetylcholinesterase inhibitor Drugs 0.000 claims 1
- 102000001301 EGF receptor Human genes 0.000 claims 1
- 108060006698 EGF receptor Proteins 0.000 claims 1
- 229940099433 NMDA receptor antagonist Drugs 0.000 claims 1
- 102000002002 Neurokinin-1 Receptors Human genes 0.000 claims 1
- 108010040718 Neurokinin-1 Receptors Proteins 0.000 claims 1
- AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 claims 1
- 102000001938 Plasminogen Activators Human genes 0.000 claims 1
- 108010001014 Plasminogen Activators Proteins 0.000 claims 1
- 102000004257 Potassium Channel Human genes 0.000 claims 1
- 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 claims 1
- 101710100968 Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 claims 1
- 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 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 239000005557 antagonist Substances 0.000 claims 1
- 230000001028 anti-proliverative effect Effects 0.000 claims 1
- 230000000561 anti-psychotic effect Effects 0.000 claims 1
- 239000000164 antipsychotic agent Substances 0.000 claims 1
- 229940005529 antipsychotics Drugs 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 229960001058 bupropion Drugs 0.000 claims 1
- SNPPWIUOZRMYNY-UHFFFAOYSA-N bupropion Chemical compound CC(C)(C)NC(C)C(=O)C1=CC=CC(Cl)=C1 SNPPWIUOZRMYNY-UHFFFAOYSA-N 0.000 claims 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 1
- 229960000590 celecoxib Drugs 0.000 claims 1
- 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 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229960003530 donepezil Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 229960002464 fluoxetine Drugs 0.000 claims 1
- 229960004038 fluvoxamine Drugs 0.000 claims 1
- 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 1
- 229960000647 gepirone Drugs 0.000 claims 1
- 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 1
- 239000003102 growth factor Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 230000003340 mental effect Effects 0.000 claims 1
- PHZVRRSCRSXGHD-UHFFFAOYSA-N methyl 1-oxo-4-[2-[[4-(trifluoromethyl)pyridin-2-yl]amino]ethylamino]-2h-[1,2,4]triazolo[4,3-a]quinoxaline-7-carboxylate Chemical compound C=1C(C(=O)OC)=CC=C(N2C(=O)NN=C22)C=1N=C2NCCNC1=CC(C(F)(F)F)=CC=N1 PHZVRRSCRSXGHD-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000003703 n methyl dextro aspartic acid receptor blocking agent Substances 0.000 claims 1
- XWFXKXYAFRWLTG-UHFFFAOYSA-N n,n-dimethyl-1-oxo-4-(propan-2-ylamino)-2h-[1,2,4]triazolo[4,3-a]quinoxaline-8-carboxamide Chemical compound C1=C(C(=O)N(C)C)C=C2N3C(=O)NN=C3C(NC(C)C)=NC2=C1 XWFXKXYAFRWLTG-UHFFFAOYSA-N 0.000 claims 1
- PHMQDMJLAIPHEE-UHFFFAOYSA-N n-(2-methoxyethyl)-1-oxo-4-(propan-2-ylamino)-2h-[1,2,4]triazolo[4,3-a]quinoxaline-8-carboxamide Chemical compound N1=C(NC(C)C)C2=NNC(=O)N2C2=CC(C(=O)NCCOC)=CC=C21 PHMQDMJLAIPHEE-UHFFFAOYSA-N 0.000 claims 1
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- 239000004090 neuroprotective agent Substances 0.000 claims 1
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- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
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| US45850003P | 2003-03-27 | 2003-03-27 | |
| PCT/IB2004/000835 WO2004085439A1 (en) | 2003-03-27 | 2004-03-15 | Substituted 4-amino[1,2,4]triazolo[4,3-a]quinoxalines |
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| ATE369370T1 (de) | 2003-10-10 | 2007-08-15 | Pfizer Prod Inc | Substituierte 2h-(1,2,4)triazolo(4,3-a)pyrazine als gsk-3-inhibitoren |
| WO2005074917A1 (en) * | 2004-01-30 | 2005-08-18 | Axonyx, Inc. | Methods for treatment of complications of diabetes |
| US7453002B2 (en) * | 2004-06-15 | 2008-11-18 | Bristol-Myers Squibb Company | Five-membered heterocycles useful as serine protease inhibitors |
| CA2620333A1 (en) | 2005-08-26 | 2007-03-01 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation |
| EP2258357A3 (en) | 2005-08-26 | 2011-04-06 | Braincells, Inc. | Neurogenesis with acetylcholinesterase inhibitor |
| ES2273599B1 (es) * | 2005-10-14 | 2008-06-01 | Universidad De Barcelona | Compuestos para el tratamiento de la fibrilacion auricular. |
| JP2009512711A (ja) | 2005-10-21 | 2009-03-26 | ブレインセルス，インコーポレイティド | Ｐｄｅ阻害による神経新生の調節 |
| US20070112017A1 (en) | 2005-10-31 | 2007-05-17 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| CA2636043A1 (en) * | 2006-01-23 | 2007-08-02 | Amira Pharmaceuticals, Inc. | Tricyclic inhibitors of 5-lipoxygenase |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| EP2382975A3 (en) | 2006-05-09 | 2012-02-29 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| EP2535336A1 (en) * | 2006-10-21 | 2012-12-19 | Abbott GmbH & Co. KG | Heterocyclic compounds and their use as glycogen synthase kinase 3 inhibitors |
| WO2009017453A1 (en) * | 2007-07-30 | 2009-02-05 | Astrazeneca Ab | New therapeutic combination of an antipsychotic and a gsk3 inhibitor 958 |
| GB0719299D0 (en) | 2007-10-03 | 2007-11-14 | Optinose As | Nasal delivery devices |
| WO2010099217A1 (en) | 2009-02-25 | 2010-09-02 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| MX2011009314A (es) | 2009-03-05 | 2011-10-11 | Astellas Pharma Inc | Compuesto de quinoxalina. |
| US8481547B2 (en) * | 2009-12-18 | 2013-07-09 | Janssen Pharmaceutica Nv | Substituted benzothiazole and benzoxazole derivatives useful as inhibitors of DPP-1 |
| KR20130097178A (ko) | 2010-09-07 | 2013-09-02 | 아스텔라스세이야쿠 가부시키가이샤 | 퀴녹살린 화합물 |
| US9540379B2 (en) * | 2011-01-31 | 2017-01-10 | Boehringer Ingelheim International Gmbh | (1,2,4)triazolo[4,3-A]quinoxaline derivatives as inhibitors of phosphodiesterases |
| HRP20181310T1 (hr) | 2011-09-30 | 2018-10-19 | C&C Research Laboratories | Novi heterociklički derivati i njihova uporaba |
| US20140045856A1 (en) | 2012-07-31 | 2014-02-13 | Boehringer Ingelheim International Gmbh | 4-Methyl-2,3,5,9,9b-pentaaza-cyclopenta[a]naphthalenes |
| US10154988B2 (en) | 2012-11-14 | 2018-12-18 | The Johns Hopkins University | Methods and compositions for treating schizophrenia |
| TW202021969A (zh) * | 2018-05-31 | 2020-06-16 | 南韓商Ｃ＆Ｃ新藥研究所 | 雜環衍生物及其用途 |
| SI3823971T1 (sl) * | 2018-07-20 | 2022-10-28 | Gruenenthal Gmbh | Substituirani derivati triazolokinoksalina |
| CN116462676A (zh) * | 2022-01-20 | 2023-07-21 | 上海和誉生物医药科技有限公司 | 一种多稠环prmt5抑制剂及其制备方法和应用 |
| AU2023319559A1 (en) * | 2022-08-03 | 2024-11-07 | Abbisko Therapeutics Co., Ltd. | Nitrogen-containing fused three ring prmt5 inhibitor, and preparation method therefor and pharmaceutical use thereof |
| WO2024032572A1 (zh) * | 2022-08-09 | 2024-02-15 | 上海湃隆生物科技有限公司 | 新型prmt5抑制剂及其应用 |
| KR20250073451A (ko) * | 2022-09-26 | 2025-05-27 | 상하이 아페이론 테라퓨틱스 컴퍼니 리미티드 | 신형 prmt5 억제제 및 그 응용 |
| WO2025077857A1 (zh) * | 2023-10-13 | 2025-04-17 | 上海湃隆生物科技有限公司 | Prmt5抑制剂在治疗肿瘤或癌症中的用途 |
| WO2025180350A1 (zh) * | 2024-02-26 | 2025-09-04 | 上海湃隆生物科技有限公司 | 化合物盐的晶型及其制备方法和用途 |
| WO2025180349A1 (zh) * | 2024-02-26 | 2025-09-04 | 上海湃隆生物科技有限公司 | 化合物的固体及其制备方法和用途 |
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| US103185A (en) * | 1870-05-17 | Improvement in combined rake and reel for harvesters | ||
| TR200001728T2 (tr) * | 1997-11-11 | 2000-09-21 | Ono Pharmaceutical Co., Ltd. | Birleşik pirazin türevleri |
| AU2509602A (en) * | 2000-12-20 | 2002-07-01 | Sod Conseils Rech Applic | Cyclin-dependent kinase (CDK) and glycolene synthase kinase-3 (GSK-3) inhibitors |
| US20020115635A1 (en) * | 2001-02-21 | 2002-08-22 | Pnina Fishman | Modulation of GSK-3beta activity and its different uses |
| WO2002083140A1 (en) * | 2001-04-10 | 2002-10-24 | Merck & Co., Inc. | Inhibitors of akt activity |
| EP1295885A1 (en) * | 2001-09-21 | 2003-03-26 | Sanofi-Synthelabo | Substituted 2-pyridinyl-6,7,8,9-tetrahydropyrimido(1,2-a)pyrimidin-4-one and 7-pyridinyl-2,3-dihydroimidazo(1,2-a)pyrimidin-5(1H)one derivatives |
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2004
- 2004-03-15 CA CA002520251A patent/CA2520251A1/en not_active Abandoned
- 2004-03-15 JP JP2006506368A patent/JP2006521343A/ja not_active Withdrawn
- 2004-03-15 BR BRPI0407926-4A patent/BRPI0407926A/pt not_active IP Right Cessation
- 2004-03-15 EP EP04720674A patent/EP1613629A1/en not_active Withdrawn
- 2004-03-15 MX MXPA05010293A patent/MXPA05010293A/es unknown
- 2004-03-15 WO PCT/IB2004/000835 patent/WO2004085439A1/en not_active Ceased
- 2004-03-22 US US10/805,885 patent/US7202245B2/en not_active Expired - Fee Related
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