JP2006521343A - 置換４−アミノ［１，２，４］トリアゾロ［４，３−ａ］キノキサリン - Google Patents
置換４−アミノ［１，２，４］トリアゾロ［４，３−ａ］キノキサリン Download PDFInfo
- Publication number
- JP2006521343A JP2006521343A JP2006506368A JP2006506368A JP2006521343A JP 2006521343 A JP2006521343 A JP 2006521343A JP 2006506368 A JP2006506368 A JP 2006506368A JP 2006506368 A JP2006506368 A JP 2006506368A JP 2006521343 A JP2006521343 A JP 2006521343A
- 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- Withdrawn
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- 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 122
- 239000000203 mixture Substances 0.000 claims abstract description 78
- 239000000651 prodrug Substances 0.000 claims abstract description 49
- 229940002612 prodrug Drugs 0.000 claims abstract description 49
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 239000003112 inhibitor Substances 0.000 claims abstract description 26
- 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 claims abstract description 23
- 201000010099 disease Diseases 0.000 claims abstract description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 14
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 10
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- 208000024827 Alzheimer disease 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
- 231100000360 alopecia Toxicity 0.000 claims abstract description 6
- 201000011510 cancer Diseases 0.000 claims abstract description 6
- 206010012289 Dementia Diseases 0.000 claims abstract description 5
- 208000006011 Stroke Diseases 0.000 claims abstract description 3
- 102000001267 GSK3 Human genes 0.000 claims abstract 5
- -1 -COR 5 Chemical group 0.000 claims description 52
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 41
- 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
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 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 14
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 14
- 241000124008 Mammalia Species 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 230000000694 effects Effects 0.000 claims description 11
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 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
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 claims description 6
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- 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
- 239000004037 angiogenesis inhibitor 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
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 claims description 5
- 159000000000 sodium salts Chemical class 0.000 claims description 5
- 229940100578 Acetylcholinesterase inhibitor Drugs 0.000 claims description 4
- 102000001301 EGF receptor Human genes 0.000 claims description 4
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- 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
- 208000006673 asthma Diseases 0.000 claims description 4
- 230000004054 inflammatory process Effects 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000004090 neuroprotective agent Substances 0.000 claims description 4
- 235000020824 obesity Nutrition 0.000 claims description 4
- 108020001213 potassium channel Proteins 0.000 claims description 4
- 230000011664 signaling Effects 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
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 3
- 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 3
- 208000019901 Anxiety disease Diseases 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 208000007530 Essential hypertension Diseases 0.000 claims description 3
- 206010019280 Heart failures Diseases 0.000 claims description 3
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- 208000013016 Hypoglycemia Diseases 0.000 claims description 3
- 208000021384 Obsessive-Compulsive disease 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
- 230000005856 abnormality Effects 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 230000001028 anti-proliverative effect Effects 0.000 claims description 3
- 230000000561 anti-psychotic effect Effects 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 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 3
- 230000035558 fertility Effects 0.000 claims description 3
- 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
- 230000016273 neuron death Effects 0.000 claims description 3
- 210000000440 neutrophil Anatomy 0.000 claims description 3
- 230000002611 ovarian Effects 0.000 claims description 3
- 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 3
- 229960000371 rofecoxib Drugs 0.000 claims description 3
- 230000019100 sperm motility Effects 0.000 claims description 3
- 230000009529 traumatic brain injury Effects 0.000 claims description 3
- 230000003313 weakening effect Effects 0.000 claims description 3
- MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound 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
- 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 description 2
- 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 description 2
- 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 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
- 229920002527 Glycogen Polymers 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
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 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
- 229960003530 donepezil Drugs 0.000 claims description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 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
- 229940096919 glycogen Drugs 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229960005017 olanzapine Drugs 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
- 229960002296 paroxetine Drugs 0.000 claims description 2
- 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
- 239000004001 serotonin 1D antagonist Substances 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
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- 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
- 229960001685 tacrine Drugs 0.000 claims description 2
- YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-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
- 229960002004 valdecoxib Drugs 0.000 claims description 2
- 229960000607 ziprasidone Drugs 0.000 claims description 2
- 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
- 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
- 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
- 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
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Classifications
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Diabetes (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Obesity (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Hospice & Palliative Care (AREA)
- Pulmonology (AREA)
- Child & Adolescent Psychology (AREA)
- Rheumatology (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006521343A true JP2006521343A (ja) | 2006-09-21 |
| JP2006521343A5 JP2006521343A5 (https=) | 2007-04-05 |
Family
ID=33098270
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006506368A Withdrawn JP2006521343A (ja) | 2003-03-27 | 2004-03-15 | 置換４−アミノ［１，２，４］トリアゾロ［４，３−ａ］キノキサリン |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7202245B2 (https=) |
| EP (1) | EP1613629A1 (https=) |
| JP (1) | JP2006521343A (https=) |
| BR (1) | BRPI0407926A (https=) |
| CA (1) | CA2520251A1 (https=) |
| MX (1) | MXPA05010293A (https=) |
| WO (1) | WO2004085439A1 (https=) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010507575A (ja) * | 2006-10-21 | 2010-03-11 | アボット ゲーエムベーハー ウント カンパニー カーゲー | 複素環化合物およびそれらのグリコーゲンシンターゼキナーゼ３阻害薬としての使用 |
| JP2025516926A (ja) * | 2022-08-03 | 2025-05-30 | アビスコ セラピューティクス カンパニー リミテッド | 窒素含有三縮合環ｐｒｍｔ５阻害剤、その製造方法および薬学上の用途 |
| JP2025533677A (ja) * | 2022-09-26 | 2025-10-07 | 上海湃隆生物科技有限公司 | 新型ｐｒｍｔ５阻害剤およびその使用 |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2541832C (en) | 2003-10-10 | 2009-11-24 | Pfizer Products Inc. | Substituted 2h-[1,2,4]triazolo[4,3-a]pyrazines as gsk-3 inhibitors |
| 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 |
| EP1928437A2 (en) | 2005-08-26 | 2008-06-11 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation |
| EP2258358A3 (en) | 2005-08-26 | 2011-09-07 | 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. |
| EP1940389A2 (en) | 2005-10-21 | 2008-07-09 | Braincells, Inc. | Modulation of neurogenesis by pde inhibition |
| US20070112017A1 (en) | 2005-10-31 | 2007-05-17 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| JP2009523820A (ja) * | 2006-01-23 | 2009-06-25 | アミラ ファーマシューティカルス，インコーポレーテッド | ５−リポキシゲナーゼの三環系抑制剤 |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| AU2007249399A1 (en) | 2006-05-09 | 2007-11-22 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| 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 |
| WO2010101230A1 (ja) | 2009-03-05 | 2010-09-10 | アステラス製薬株式会社 | キノキサリン化合物 |
| US8481547B2 (en) * | 2009-12-18 | 2013-07-09 | Janssen Pharmaceutica Nv | Substituted benzothiazole and benzoxazole derivatives useful as inhibitors of DPP-1 |
| BR112013005439A2 (pt) | 2010-09-07 | 2017-09-19 | Astellas Pharma Inc | compostos de quinoxalina |
| 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 |
| TWI551600B (zh) | 2011-09-30 | 2016-10-01 | Ｃ＆Ｃ新藥研究所 | 新穎雜環衍生物及其用途 |
| US20140045856A1 (en) | 2012-07-31 | 2014-02-13 | Boehringer Ingelheim International Gmbh | 4-Methyl-2,3,5,9,9b-pentaaza-cyclopenta[a]naphthalenes |
| US20140206667A1 (en) | 2012-11-14 | 2014-07-24 | Michela Gallagher | 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 |
| IL280212B2 (en) * | 2018-07-20 | 2023-09-01 | Gruenenthal Chemie | Transmuted triazoloquinoxaline histories |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US103185A (en) * | 1870-05-17 | Improvement in combined rake and reel for harvesters | ||
| CN1285834A (zh) * | 1997-11-11 | 2001-02-28 | 小野药品工业株式会社 | 稠合吡嗪化合物 |
| EP1345941A1 (fr) * | 2000-12-20 | 2003-09-24 | Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S.) | Inhibiteurs de kinases dependantes des cylines (cdk) et de la glycogene synthase kinase-3 (gsk-3) |
| 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 |
-
2004
- 2004-03-15 BR BRPI0407926-4A patent/BRPI0407926A/pt not_active IP Right Cessation
- 2004-03-15 MX MXPA05010293A patent/MXPA05010293A/es unknown
- 2004-03-15 EP EP04720674A patent/EP1613629A1/en not_active Withdrawn
- 2004-03-15 WO PCT/IB2004/000835 patent/WO2004085439A1/en not_active Ceased
- 2004-03-15 CA CA002520251A patent/CA2520251A1/en not_active Abandoned
- 2004-03-15 JP JP2006506368A patent/JP2006521343A/ja not_active Withdrawn
- 2004-03-22 US US10/805,885 patent/US7202245B2/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010507575A (ja) * | 2006-10-21 | 2010-03-11 | アボット ゲーエムベーハー ウント カンパニー カーゲー | 複素環化合物およびそれらのグリコーゲンシンターゼキナーゼ３阻害薬としての使用 |
| JP2025516926A (ja) * | 2022-08-03 | 2025-05-30 | アビスコ セラピューティクス カンパニー リミテッド | 窒素含有三縮合環ｐｒｍｔ５阻害剤、その製造方法および薬学上の用途 |
| JP2025533677A (ja) * | 2022-09-26 | 2025-10-07 | 上海湃隆生物科技有限公司 | 新型ｐｒｍｔ５阻害剤およびその使用 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1613629A1 (en) | 2006-01-11 |
| MXPA05010293A (es) | 2005-11-17 |
| US20040192698A1 (en) | 2004-09-30 |
| BRPI0407926A (pt) | 2006-02-21 |
| CA2520251A1 (en) | 2004-10-07 |
| US7202245B2 (en) | 2007-04-10 |
| WO2004085439A1 (en) | 2004-10-07 |
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