JP2007508290A5 - - Google Patents
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- Publication number
- JP2007508290A5 JP2007508290A5 JP2006530734A JP2006530734A JP2007508290A5 JP 2007508290 A5 JP2007508290 A5 JP 2007508290A5 JP 2006530734 A JP2006530734 A JP 2006530734A JP 2006530734 A JP2006530734 A JP 2006530734A JP 2007508290 A5 JP2007508290 A5 JP 2007508290A5
- Authority
- JP
- Japan
- Prior art keywords
- independently
- alkyl
- optionally substituted
- substituted
- triazolo
- 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.)
- Pending
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 27
- 229910052736 halogen Inorganic materials 0.000 claims 27
- 150000002367 halogens Chemical class 0.000 claims 21
- 125000003118 aryl group Chemical group 0.000 claims 18
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 18
- 125000001072 heteroaryl group Chemical group 0.000 claims 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims 15
- 125000003545 alkoxy group Chemical group 0.000 claims 13
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 11
- 239000000651 prodrug Substances 0.000 claims 11
- 229940002612 prodrug Drugs 0.000 claims 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- -1 methylenedioxy Chemical group 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000003107 substituted aryl group Chemical group 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 239000003112 inhibitor Substances 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims 3
- 102000001267 GSK3 Human genes 0.000 claims 3
- 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 208000024891 symptom Diseases 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
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- 206010012289 Dementia Diseases 0.000 claims 2
- 208000007530 Essential hypertension Diseases 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
- 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
- 208000006011 Stroke Diseases 0.000 claims 2
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 2
- 239000004037 angiogenesis inhibitor Substances 0.000 claims 2
- 239000000164 antipsychotic agent Substances 0.000 claims 2
- 230000036506 anxiety Effects 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
- 206010012601 diabetes mellitus Diseases 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
- BNKVGZXDUVAYFS-UHFFFAOYSA-N ethyl 4-[(6-tert-butyl-3-oxo-2h-[1,2,4]triazolo[4,3-a]pyrazin-8-yl)amino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1NC1=NC(C(C)(C)C)=CN2C(=O)NN=C12 BNKVGZXDUVAYFS-UHFFFAOYSA-N 0.000 claims 2
- 230000035558 fertility Effects 0.000 claims 2
- 208000024963 hair loss Diseases 0.000 claims 2
- 230000003676 hair loss Effects 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
- 239000000203 mixture Substances 0.000 claims 2
- 230000016273 neuron death Effects 0.000 claims 2
- 239000004090 neuroprotective agent Substances 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 208000015124 ovarian disease Diseases 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 239000002464 receptor antagonist Substances 0.000 claims 2
- 229940044551 receptor antagonist Drugs 0.000 claims 2
- 201000000980 schizophrenia Diseases 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
- 239000011593 sulfur Substances 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 230000009529 traumatic brain injury 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
- 125000004191 (C1-C6) alkoxy 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
- POLAUOGHQIDJOL-UHFFFAOYSA-N 3-[(6-tert-butyl-3-oxo-2h-[1,2,4]triazolo[4,3-a]pyrazin-8-yl)amino]propanenitrile Chemical compound N#CCCNC1=NC(C(C)(C)C)=CN2C(=O)NN=C21 POLAUOGHQIDJOL-UHFFFAOYSA-N 0.000 claims 1
- ZVICCLKJAFIQPK-UHFFFAOYSA-N 5-methyl-6-propan-2-yl-8-(2-pyridin-3-ylethylamino)-2h-[1,2,4]triazolo[4,3-a]pyrazin-3-one Chemical compound C12=NNC(=O)N2C(C)=C(C(C)C)N=C1NCCC1=CC=CN=C1 ZVICCLKJAFIQPK-UHFFFAOYSA-N 0.000 claims 1
- AGKIGFGRCKEUIU-UHFFFAOYSA-N 6-tert-butyl-8-(1-hydroxypropan-2-ylamino)-2h-[1,2,4]triazolo[4,3-a]pyrazin-3-one Chemical compound OCC(C)NC1=NC(C(C)(C)C)=CN2C(=O)NN=C12 AGKIGFGRCKEUIU-UHFFFAOYSA-N 0.000 claims 1
- BDHXUVFUQBVLKW-UHFFFAOYSA-N 6-tert-butyl-8-(2-ethylsulfanylethylamino)-2h-[1,2,4]triazolo[4,3-a]pyrazin-3-one Chemical compound CCSCCNC1=NC(C(C)(C)C)=CN2C(=O)NN=C12 BDHXUVFUQBVLKW-UHFFFAOYSA-N 0.000 claims 1
- RGSWWBAMGAFCQA-UHFFFAOYSA-N 6-tert-butyl-8-(2-methoxyethylamino)-2h-[1,2,4]triazolo[4,3-a]pyrazin-3-one Chemical compound COCCNC1=NC(C(C)(C)C)=CN2C(=O)NN=C12 RGSWWBAMGAFCQA-UHFFFAOYSA-N 0.000 claims 1
- QXUHWSNAOLAIHF-UHFFFAOYSA-N 6-tert-butyl-8-(2-pyridin-3-yloxyethylamino)-2h-[1,2,4]triazolo[4,3-a]pyrazin-3-one Chemical compound N=1C(C(C)(C)C)=CN(C(NN=2)=O)C=2C=1NCCOC1=CC=CN=C1 QXUHWSNAOLAIHF-UHFFFAOYSA-N 0.000 claims 1
- OCDKRJXMBSTSLF-UHFFFAOYSA-N 6-tert-butyl-8-(2-pyridin-4-yloxyethylamino)-2h-[1,2,4]triazolo[4,3-a]pyrazin-3-one Chemical compound N=1C(C(C)(C)C)=CN(C(NN=2)=O)C=2C=1NCCOC1=CC=NC=C1 OCDKRJXMBSTSLF-UHFFFAOYSA-N 0.000 claims 1
- MADZBIDQNUJHGS-UHFFFAOYSA-N 6-tert-butyl-8-(3-imidazol-1-ylpropylamino)-2h-[1,2,4]triazolo[4,3-a]pyrazin-3-one Chemical compound N=1C(C(C)(C)C)=CN(C(NN=2)=O)C=2C=1NCCCN1C=CN=C1 MADZBIDQNUJHGS-UHFFFAOYSA-N 0.000 claims 1
- OVWGZKPAZNUTCZ-UHFFFAOYSA-N 6-tert-butyl-8-(3-methoxypropylamino)-2h-[1,2,4]triazolo[4,3-a]pyrazin-3-one Chemical compound COCCCNC1=NC(C(C)(C)C)=CN2C(=O)NN=C12 OVWGZKPAZNUTCZ-UHFFFAOYSA-N 0.000 claims 1
- NSRHZPWFEUPBDQ-UHFFFAOYSA-N 6-tert-butyl-8-(3-morpholin-4-ylpropylamino)-2h-[1,2,4]triazolo[4,3-a]pyrazin-3-one Chemical compound N=1C(C(C)(C)C)=CN(C(NN=2)=O)C=2C=1NCCCN1CCOCC1 NSRHZPWFEUPBDQ-UHFFFAOYSA-N 0.000 claims 1
- KXZONCXHEBLIPF-UHFFFAOYSA-N 6-tert-butyl-8-(6-hydroxyhexylamino)-2h-[1,2,4]triazolo[4,3-a]pyrazin-3-one Chemical compound OCCCCCCNC1=NC(C(C)(C)C)=CN2C(=O)NN=C21 KXZONCXHEBLIPF-UHFFFAOYSA-N 0.000 claims 1
- GYXFKTYCDZYNGD-UHFFFAOYSA-N 6-tert-butyl-8-(oxolan-2-ylmethylamino)-2h-[1,2,4]triazolo[4,3-a]pyrazin-3-one Chemical compound N=1C(C(C)(C)C)=CN(C(NN=2)=O)C=2C=1NCC1CCCO1 GYXFKTYCDZYNGD-UHFFFAOYSA-N 0.000 claims 1
- CYENWPOUSLGVMZ-UHFFFAOYSA-N 6-tert-butyl-8-(pyridin-3-ylmethylamino)-2h-[1,2,4]triazolo[4,3-a]pyrazin-3-one Chemical compound N=1C(C(C)(C)C)=CN(C(NN=2)=O)C=2C=1NCC1=CC=CN=C1 CYENWPOUSLGVMZ-UHFFFAOYSA-N 0.000 claims 1
- QUHBCBXUVIHAIR-UHFFFAOYSA-N 6-tert-butyl-8-(pyridin-4-ylmethylamino)-2h-[1,2,4]triazolo[4,3-a]pyrazin-3-one Chemical compound N=1C(C(C)(C)C)=CN(C(NN=2)=O)C=2C=1NCC1=CC=NC=C1 QUHBCBXUVIHAIR-UHFFFAOYSA-N 0.000 claims 1
- BGUMMDJJAIJMCP-UHFFFAOYSA-N 6-tert-butyl-8-[(4-nitrophenyl)methylamino]-2h-[1,2,4]triazolo[4,3-a]pyrazin-3-one Chemical compound N=1C(C(C)(C)C)=CN(C(NN=2)=O)C=2C=1NCC1=CC=C([N+]([O-])=O)C=C1 BGUMMDJJAIJMCP-UHFFFAOYSA-N 0.000 claims 1
- PLJTUDBAKXBITC-UHFFFAOYSA-N 6-tert-butyl-8-[2-(2-methylpyridin-3-yl)ethylamino]-2h-[1,2,4]triazolo[4,3-a]pyrazin-3-one Chemical compound CC1=NC=CC=C1CCNC1=NC(C(C)(C)C)=CN2C(=O)NN=C12 PLJTUDBAKXBITC-UHFFFAOYSA-N 0.000 claims 1
- HIWMBFPGVAHHPE-UHFFFAOYSA-N 6-tert-butyl-8-[2-(2-methylpyridin-3-yl)oxyethylamino]-2h-[1,2,4]triazolo[4,3-a]pyrazin-3-one Chemical compound CC1=NC=CC=C1OCCNC1=NC(C(C)(C)C)=CN2C(=O)NN=C12 HIWMBFPGVAHHPE-UHFFFAOYSA-N 0.000 claims 1
- HYQVWXMXOTZEPD-UHFFFAOYSA-N 6-tert-butyl-8-[2-(4-methoxyphenoxy)ethylamino]-2h-[1,2,4]triazolo[4,3-a]pyrazin-3-one Chemical compound C1=CC(OC)=CC=C1OCCNC1=NC(C(C)(C)C)=CN2C(=O)NN=C12 HYQVWXMXOTZEPD-UHFFFAOYSA-N 0.000 claims 1
- JWOZTMKXSCELPG-UHFFFAOYSA-N 6-tert-butyl-8-[2-(4-methyl-1h-benzimidazol-2-yl)ethylamino]-2h-[1,2,4]triazolo[4,3-a]pyrazin-3-one Chemical compound CC(C)(C)C1=CN2C(=O)NN=C2C(NCCC2=NC=3C=CC=C(C=3N2)C)=N1 JWOZTMKXSCELPG-UHFFFAOYSA-N 0.000 claims 1
- SXHAFJZKPXLKGL-UHFFFAOYSA-N 6-tert-butyl-8-[2-(6-methoxypyridin-3-yl)ethylamino]-2h-[1,2,4]triazolo[4,3-a]pyrazin-3-one Chemical compound C1=NC(OC)=CC=C1CCNC1=NC(C(C)(C)C)=CN2C(=O)NN=C12 SXHAFJZKPXLKGL-UHFFFAOYSA-N 0.000 claims 1
- HXZQTJWJZWAEFZ-UHFFFAOYSA-N 6-tert-butyl-8-[2-(6-methylpyridin-3-yl)ethylamino]-2h-[1,2,4]triazolo[4,3-a]pyrazin-3-one Chemical compound C1=NC(C)=CC=C1CCNC1=NC(C(C)(C)C)=CN2C(=O)NN=C12 HXZQTJWJZWAEFZ-UHFFFAOYSA-N 0.000 claims 1
- KYWIRYJDXDTYTP-UHFFFAOYSA-N 6-tert-butyl-8-[3-(2-oxopyrrolidin-1-yl)propylamino]-2h-[1,2,4]triazolo[4,3-a]pyrazin-3-one Chemical compound N=1C(C(C)(C)C)=CN(C(NN=2)=O)C=2C=1NCCCN1CCCC1=O KYWIRYJDXDTYTP-UHFFFAOYSA-N 0.000 claims 1
- RJFYCUAWRSFYHY-UHFFFAOYSA-N 6-tert-butyl-8-[3-(3,5-dimethylpyrazol-1-yl)propylamino]-2h-[1,2,4]triazolo[4,3-a]pyrazin-3-one Chemical compound N1=C(C)C=C(C)N1CCCNC1=NC(C(C)(C)C)=CN2C(=O)NN=C12 RJFYCUAWRSFYHY-UHFFFAOYSA-N 0.000 claims 1
- IMRPZUHUKOZYAK-UHFFFAOYSA-N 8-[2-(1,3-benzothiazol-2-ylamino)ethylamino]-6-tert-butyl-2h-[1,2,4]triazolo[4,3-a]pyrazin-3-one Chemical compound C1=CC=C2SC(NCCNC=3C=4N(C(NN=4)=O)C=C(N=3)C(C)(C)C)=NC2=C1 IMRPZUHUKOZYAK-UHFFFAOYSA-N 0.000 claims 1
- WVLKZLVPJXMADI-UHFFFAOYSA-N 8-[2-(3-aminopyridin-2-yl)oxyethylamino]-6-tert-butyl-2h-[1,2,4]triazolo[4,3-a]pyrazin-3-one Chemical compound N=1C(C(C)(C)C)=CN(C(NN=2)=O)C=2C=1NCCOC1=NC=CC=C1N WVLKZLVPJXMADI-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
- 208000036119 Frailty Diseases 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
- PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Natural products C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-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
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 230000001028 anti-proliverative effect Effects 0.000 claims 1
- 229940005529 antipsychotics Drugs 0.000 claims 1
- 206010003549 asthenia Diseases 0.000 claims 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 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
- 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
- 229960003530 donepezil Drugs 0.000 claims 1
- 230000000694 effects Effects 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
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 229960001952 metrifonate Drugs 0.000 claims 1
- 229960001800 nefazodone Drugs 0.000 claims 1
- VRBKIVRKKCLPHA-UHFFFAOYSA-N nefazodone Chemical compound O=C1N(CCOC=2C=CC=CC=2)C(CC)=NN1CCCN(CC1)CCN1C1=CC=CC(Cl)=C1 VRBKIVRKKCLPHA-UHFFFAOYSA-N 0.000 claims 1
- 210000000440 neutrophil Anatomy 0.000 claims 1
- 229960002296 paroxetine Drugs 0.000 claims 1
- 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 1
- 229960001697 physostigmine Drugs 0.000 claims 1
- 229940127126 plasminogen activator Drugs 0.000 claims 1
- 108020001213 potassium channel Proteins 0.000 claims 1
- 229960004136 rivastigmine Drugs 0.000 claims 1
- 229960000371 rofecoxib Drugs 0.000 claims 1
- 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 1
- 239000004001 serotonin 1D antagonist Substances 0.000 claims 1
- 229960002073 sertraline Drugs 0.000 claims 1
- 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 1
- 229960001685 tacrine Drugs 0.000 claims 1
- YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 claims 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 claims 1
- 229960002004 valdecoxib Drugs 0.000 claims 1
- 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 1
- 239000002525 vasculotropin inhibitor Substances 0.000 claims 1
- 229960004688 venlafaxine Drugs 0.000 claims 1
- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 claims 1
- 230000003313 weakening effect Effects 0.000 claims 1
- 0 *C(N(C1=NN2)C2=O)=C(*)N=C1N(*)* Chemical compound *C(N(C1=NN2)C2=O)=C(*)N=C1N(*)* 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51022403P | 2003-10-10 | 2003-10-10 | |
| PCT/IB2004/003137 WO2005035532A1 (en) | 2003-10-10 | 2004-09-27 | Substituted 2h-[1,2,4]triazolo[4,3-a]pyrazines as gsk-3 inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007508290A JP2007508290A (ja) | 2007-04-05 |
| JP2007508290A5 true JP2007508290A5 (https=) | 2007-10-11 |
Family
ID=34435073
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006530734A Pending JP2007508290A (ja) | 2003-10-10 | 2004-09-27 | ＧＳＫ−３阻害剤としての置換２Ｈ−［１，２，４］トリアゾロ［４，３−ａ］ピラジン |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7709473B2 (https=) |
| EP (1) | EP1678180B1 (https=) |
| JP (1) | JP2007508290A (https=) |
| AT (1) | ATE369370T1 (https=) |
| BR (1) | BRPI0415185A (https=) |
| CA (1) | CA2541832C (https=) |
| DE (1) | DE602004008098T8 (https=) |
| ES (1) | ES2288270T3 (https=) |
| MX (1) | MXPA06004043A (https=) |
| WO (1) | WO2005035532A1 (https=) |
Families Citing this family (65)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1875021A (zh) | 2003-11-04 | 2006-12-06 | 默克公司 | 取代的萘啶酮衍生物 |
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-
2004
- 2004-09-27 BR BRPI0415185-2A patent/BRPI0415185A/pt not_active IP Right Cessation
- 2004-09-27 ES ES04769486T patent/ES2288270T3/es not_active Expired - Lifetime
- 2004-09-27 MX MXPA06004043A patent/MXPA06004043A/es not_active Application Discontinuation
- 2004-09-27 US US10/575,395 patent/US7709473B2/en not_active Expired - Fee Related
- 2004-09-27 EP EP04769486A patent/EP1678180B1/en not_active Expired - Lifetime
- 2004-09-27 AT AT04769486T patent/ATE369370T1/de not_active IP Right Cessation
- 2004-09-27 WO PCT/IB2004/003137 patent/WO2005035532A1/en not_active Ceased
- 2004-09-27 CA CA002541832A patent/CA2541832C/en not_active Expired - Fee Related
- 2004-09-27 JP JP2006530734A patent/JP2007508290A/ja active Pending
- 2004-09-27 DE DE602004008098T patent/DE602004008098T8/de active Active
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