JP2007508290A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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 (enExample) | 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 (enExample) |
| EP (1) | EP1678180B1 (enExample) |
| JP (1) | JP2007508290A (enExample) |
| AT (1) | ATE369370T1 (enExample) |
| BR (1) | BRPI0415185A (enExample) |
| CA (1) | CA2541832C (enExample) |
| DE (1) | DE602004008098T8 (enExample) |
| ES (1) | ES2288270T3 (enExample) |
| MX (1) | MXPA06004043A (enExample) |
| WO (1) | WO2005035532A1 (enExample) |
Families Citing this family (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007510649A (ja) | 2003-11-04 | 2007-04-26 | メルク エンド カムパニー インコーポレーテッド | 置換ナフチリジノン誘導体 |
| EP2258359A3 (en) | 2005-08-26 | 2011-04-06 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation with sabcomelin |
| US7678363B2 (en) | 2005-08-26 | 2010-03-16 | Braincells Inc | Methods of treating psychiatric conditions comprising administration of muscarinic agents in combination with SSRIs |
| WO2007047978A2 (en) | 2005-10-21 | 2007-04-26 | Braincells, Inc. | Modulation of neurogenesis by pde inhibition |
| AU2006308889A1 (en) | 2005-10-31 | 2007-05-10 | Braincells, Inc. | GABA receptor mediated modulation of neurogenesis |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| CA2651813A1 (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 |
| DE102007012645A1 (de) * | 2007-03-16 | 2008-09-18 | Bayer Healthcare Ag | Substituierte Imidazo- und Triazolopyrimidine |
| DE102007032349A1 (de) * | 2007-07-11 | 2009-01-15 | Bayer Healthcare Ag | Imidazo-, Pyrazolopyrazine und Imidazotriazine und ihre Verwendung |
| WO2009017453A1 (en) * | 2007-07-30 | 2009-02-05 | Astrazeneca Ab | New therapeutic combination of an antipsychotic and a gsk3 inhibitor 958 |
| PE20091074A1 (es) * | 2007-12-13 | 2009-07-26 | Bayer Healthcare Ag | Triazolotriazinas y triazolopirazinas y su uso |
| DE102008023801A1 (de) * | 2008-05-15 | 2009-11-19 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Imidazo- und Triazolopyrimidine, Imidazo- und Pyrazolopyrazine und Imidazotriazine |
| WO2010099217A1 (en) | 2009-02-25 | 2010-09-02 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| JP5559604B2 (ja) * | 2009-05-27 | 2014-07-23 | 富山化学工業株式会社 | ３，６−ジクロロ−２−ピラジンカルボニトリルの製造法 |
| CA2787714C (en) | 2010-01-22 | 2019-04-09 | Joaquin Pastor Fernandez | Inhibitors of pi3 kinase |
| WO2011141713A1 (en) | 2010-05-13 | 2011-11-17 | Centro Nacional De Investigaciones Oncologicas (Cnio) | New bicyclic compounds as pi3-k and mtor inhibitors |
| HUE048859T2 (hu) | 2010-08-10 | 2020-08-28 | Rempex Pharmaceuticals Inc | Gyûrûs bórsavészter származékok, eljárás elõállításukra, és terápiás alkalmazásuk |
| WO2013033461A1 (en) | 2011-08-31 | 2013-03-07 | Rempex Pharmaceuticals, Inc. | Heterocyclic boronic acid ester derivatives and therapeutic uses thereof |
| US9156858B2 (en) | 2012-05-23 | 2015-10-13 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| US10561675B2 (en) | 2012-06-06 | 2020-02-18 | Rempex Pharmaceuticals, Inc. | Cyclic boronic acid ester derivatives and therapeutic uses thereof |
| CN103121970B (zh) * | 2012-12-04 | 2015-04-29 | 中国科学院昆明植物研究所 | 苯并咪唑及其衍生物，其药物组合物及其在制备抗抑郁药物中的应用 |
| CN103121969A (zh) * | 2012-12-04 | 2013-05-29 | 中国科学院昆明植物研究所 | 苯并咪唑及其衍生物，其药物组合物及其应用 |
| BR112015016002A2 (pt) | 2013-01-04 | 2017-07-11 | Rempex Pharmaceuticals Inc | compostos, composições farmacêuticas, complexos químicos e respectivos usos e método para tratar ou prevenir infecção bacteriana |
| CA2894891A1 (en) | 2013-01-04 | 2014-07-10 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| US9101638B2 (en) | 2013-01-04 | 2015-08-11 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| US9241947B2 (en) | 2013-01-04 | 2016-01-26 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| KR102421235B1 (ko) | 2014-02-13 | 2022-07-15 | 인사이트 코포레이션 | Lsd1 저해제로서 사이클로프로필아민 |
| US9527835B2 (en) | 2014-02-13 | 2016-12-27 | Incyte Corporation | Cyclopropylamines as LSD1 inhibitors |
| US9493442B2 (en) | 2014-02-13 | 2016-11-15 | Incyte Corporation | Cyclopropylamines as LSD1 inhibitors |
| TWI720451B (zh) | 2014-02-13 | 2021-03-01 | 美商英塞特控股公司 | 作為lsd1抑制劑之環丙胺 |
| WO2015155738A2 (en) | 2014-04-09 | 2015-10-15 | Christopher Rudd | Use of gsk-3 inhibitors or activators which modulate pd-1 or t-bet expression to modulate t cell immunity |
| WO2015171398A1 (en) | 2014-05-05 | 2015-11-12 | Rempex Pharmaceuticals, Inc. | Salts and polymorphs of cyclic boronic acid ester derivatives and therapeutic uses thereof |
| ES2750805T3 (es) | 2014-05-05 | 2020-03-27 | Rempex Pharmaceuticals Inc | Síntesis de sales de boronato y usos de las mismas |
| EA201691988A1 (ru) | 2014-05-19 | 2017-06-30 | Ремпекс Фармасьютикалз, Инк. | Производные бороновой кислоты и их терапевтическое применение |
| RU2658912C1 (ru) * | 2014-06-17 | 2018-06-26 | Шанхай Цзя Тань Фарматек Ко. Лтд. | АНАЛОГ ПИРИДИНО[1,2-А]ПИРИМИДОНА, ИСПОЛЬЗУЕМЫЙ В КАЧЕСТВЕ ИНГИБИТОРА mTOR/PI3K |
| KR102495840B1 (ko) * | 2014-06-17 | 2023-02-03 | 치아타이 티안큉 파마수티컬 그룹 주식회사 | PI3K 억제제로 사용되는 피리디노[1,2-a]피리미돈 유사체 |
| US10206937B2 (en) | 2014-07-01 | 2019-02-19 | Qpex Biopharma, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| US9758523B2 (en) | 2014-07-10 | 2017-09-12 | Incyte Corporation | Triazolopyridines and triazolopyrazines as LSD1 inhibitors |
| TW201613925A (en) | 2014-07-10 | 2016-04-16 | Incyte Corp | Imidazopyrazines as LSD1 inhibitors |
| WO2016007722A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Triazolopyridines and triazolopyrazines as lsd1 inhibitors |
| TWI687419B (zh) | 2014-07-10 | 2020-03-11 | 美商英塞特公司 | 作為ｌｓｄ１抑制劑之咪唑并吡啶及咪唑并吡嗪 |
| WO2016081297A1 (en) | 2014-11-18 | 2016-05-26 | Rempex Pharmaceuticals, Inc. | Cyclic boronic acid ester derivatives and therapeutic uses thereof |
| WO2016149393A1 (en) | 2015-03-17 | 2016-09-22 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| SG11201708047UA (en) | 2015-04-03 | 2017-10-30 | Incyte Corp | Heterocyclic compounds as lsd1 inhibitors |
| CN110402244B (zh) | 2015-08-12 | 2023-02-03 | 因赛特公司 | Lsd1抑制剂的盐 |
| SG10202010414QA (en) | 2016-04-22 | 2020-11-27 | Incyte Corp | Formulations of an lsd1 inhibitor |
| AU2017290060B2 (en) | 2016-06-30 | 2021-07-22 | Qpex Biopharma, Inc | Boronic acid derivatives and therapeutic uses thereof |
| CN107602446B (zh) * | 2016-07-12 | 2020-04-07 | 中国科学院上海药物研究所 | 1,4-双取代-1,2,3,6-四氢吡啶类化合物、其制备方法、药物组合物及其应用 |
| MY199046A (en) | 2016-07-12 | 2023-10-11 | Revolution Medicines Inc | 2,5-disubstituted 3-methyl pyrazines and 2,5,6-trisubstituted 3-methyl pyrazines as allosteric shp2 inhibitors |
| AU2018210196B2 (en) | 2017-01-23 | 2022-06-02 | Revolution Medicines, Inc. | Pyridine compounds as allosteric SHP2 inhibitors |
| SG11201906209SA (en) | 2017-01-23 | 2019-08-27 | Revolution Medicines Inc | Bicyclic compounds as allosteric shp2 inhibitors |
| BR112020007138B1 (pt) | 2017-10-11 | 2023-03-21 | Qpex Biopharma, Inc | Derivados de ácido borônico, métodos de síntese, composição farmacêutica e uso dos mesmos |
| CN111212834B (zh) | 2017-10-12 | 2024-01-19 | 锐新医药公司 | 作为变构shp2抑制剂的吡啶、吡嗪和三嗪化合物 |
| BR112020009757A2 (pt) | 2017-12-15 | 2020-11-03 | Revolution Medicines, Inc. | compostos policíclicos como inibidores alostéricos de shp2 |
| WO2019156989A1 (en) * | 2018-02-06 | 2019-08-15 | Ideaya Biosciences, Inc. | COMPOUNDS AND METHODS FOR THE MODULATION OF AhR |
| EP3781576B1 (en) | 2018-04-20 | 2024-06-12 | Qpex Biopharma, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| WO2020047198A1 (en) | 2018-08-31 | 2020-03-05 | Incyte Corporation | Salts of an lsd1 inhibitor and processes for preparing the same |
| AR131541A1 (es) | 2023-01-07 | 2025-04-09 | Syngenta Crop Protection Ag | Compuestos de carboxamida novedosos |
| WO2025032129A1 (en) | 2023-08-08 | 2025-02-13 | Syngenta Crop Protection Ag | Novel aminoindane and aminotetraline compounds |
| WO2025109114A1 (en) | 2023-11-24 | 2025-05-30 | Syngenta Crop Protection Ag | Novel carboxamide compounds |
| WO2025149629A1 (en) | 2024-01-12 | 2025-07-17 | Syngenta Crop Protection Ag | Novel carboxamide compounds |
| WO2025149637A1 (en) | 2024-01-12 | 2025-07-17 | Syngenta Crop Protection Ag | Novel carboxamide compounds |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1235910A (en) * | 1968-12-10 | 1971-06-16 | Ici Ltd | Pharmaceutical compositions |
| FR2662163A1 (fr) * | 1990-05-16 | 1991-11-22 | Lipha | Nouvelles 8-amino-1,2,4-triazolo(4,3-a) pyrazines, procedes de preparation et medicaments les contenant. |
| JP2002297477A (ja) * | 2001-03-28 | 2002-10-11 | Sony Computer Entertainment Inc | 配信システム及び配信方法 |
| EP2295550A3 (en) * | 2001-04-30 | 2011-12-14 | Vertex Pharmaceuticals Incorporated | Crystal structures of GSK-3beta protein and protein complexes and their use |
| EP1340759A1 (en) * | 2002-02-28 | 2003-09-03 | Sanofi-Synthelabo | 1-[alkyl], 1-[(heteroaryl)alkyl] and 1-[(aryl)alkyl]-7-(pyrimidin-4-yl)-imidazo[1,2-a]pyrimidin-5(1H)-one derivatives |
| CA2520251A1 (en) * | 2003-03-27 | 2004-10-07 | Pfizer Products Inc. | Substituted 4-amino[1,2,4]triazolo[4,3-a]quinoxalines |
-
2004
- 2004-09-27 US US10/575,395 patent/US7709473B2/en not_active Expired - Fee Related
- 2004-09-27 MX MXPA06004043A patent/MXPA06004043A/es not_active Application Discontinuation
- 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 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 ES ES04769486T patent/ES2288270T3/es not_active Expired - Lifetime
- 2004-09-27 DE DE602004008098T patent/DE602004008098T8/de active Active
- 2004-09-27 BR BRPI0415185-2A patent/BRPI0415185A/pt not_active IP Right Cessation
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2007508290A5 (enExample) | ||
| JP2006521343A5 (enExample) | ||
| CA2541832A1 (en) | Substituted 2h-[1,2,4]triazolo[4,3-a]pyrazines as gsk-3 inhibitors | |
| CN102171204B (zh) | 8位取代异喹啉衍生物及其用途 | |
| EP2114917B1 (en) | Pyrrole compounds | |
| JP4882748B2 (ja) | トリアゾール誘導体またはその塩 | |
| DK2432765T3 (en) | Isoquinolin-1 (2H) -ONE DERIVATIVES AS PARP-1 inhibitors | |
| CA2621181C (en) | 5-isoquinolinesulfonamide compounds | |
| WO2010114881A1 (en) | Anti-neoplastic compounds, compositions and methods | |
| ZA200406275B (en) | Substituted pyridinones as modulators of p38 map kinase | |
| JP2011506480A5 (enExample) | ||
| JP2013532692A5 (enExample) | ||
| JP2011511001A5 (enExample) | ||
| JP5922128B2 (ja) | ヒスタミンｈ４受容体リガンドとしてのベンザゾール誘導体 | |
| WO2007043457A1 (ja) | トリアリールカルボン酸誘導体 | |
| TW200813070A (en) | Antiviral agents | |
| JP2008519087A5 (enExample) | ||
| US8765972B2 (en) | 3-oxo-2,3-dihydro-1H-isoindole-4-carboxamides with selective PARP-1 inhibition | |
| WO2016118565A1 (en) | Quinazoline and quinoline compounds and uses thereof | |
| US20250179013A1 (en) | Inhibitors of rna helicase dhx9 and uses thereof | |
| AU4373600A (en) | Combination therapy for the treatment of migraine | |
| US9073893B2 (en) | 3-Oxo-2,3-dihydro-1H-indazole-4-carboxamide derivatives as PARP-1 inhibitors | |
| JP2010520917A5 (enExample) | ||
| WO2006135839A2 (en) | Piperazine-piperidine antagonists and agonists of the 5-ht1a receptor | |
| ME00952B (me) | Derivati pirazolona kao pde4 inhibitori |