JP2010059162A5 - - Google Patents
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- JP2010059162A5 JP2010059162A5 JP2009229078A JP2009229078A JP2010059162A5 JP 2010059162 A5 JP2010059162 A5 JP 2010059162A5 JP 2009229078 A JP2009229078 A JP 2009229078A JP 2009229078 A JP2009229078 A JP 2009229078A JP 2010059162 A5 JP2010059162 A5 JP 2010059162A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- phenyl
- pyrazolo
- pyridazin
- aryl
- 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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- 150000001875 compounds Chemical class 0.000 claims 96
- 125000003118 aryl group Chemical group 0.000 claims 57
- 125000001072 heteroaryl group Chemical group 0.000 claims 46
- 125000004452 carbocyclyl group Chemical group 0.000 claims 34
- 125000000623 heterocyclic group Chemical group 0.000 claims 34
- 125000001931 aliphatic group Chemical group 0.000 claims 25
- 125000003710 aryl alkyl group Chemical group 0.000 claims 22
- 239000000203 mixture Substances 0.000 claims 15
- 239000003814 drug Substances 0.000 claims 14
- 125000005843 halogen group Chemical group 0.000 claims 14
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 14
- 230000002401 inhibitory effect Effects 0.000 claims 14
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims 12
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 12
- 125000002541 furyl group Chemical group 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 125000004076 pyridyl group Chemical group 0.000 claims 12
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 12
- 125000001544 thienyl group Chemical group 0.000 claims 12
- 239000002671 adjuvant Substances 0.000 claims 11
- 239000003981 vehicle Substances 0.000 claims 11
- 239000003937 drug carrier Substances 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 125000001624 naphthyl group Chemical group 0.000 claims 8
- 238000002360 preparation method Methods 0.000 claims 8
- 102000002254 Glycogen Synthase Kinase 3 Human genes 0.000 claims 6
- 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 claims 6
- 230000000694 effects Effects 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 102000013498 tau Proteins Human genes 0.000 claims 6
- 108010026424 tau Proteins Proteins 0.000 claims 6
- JMAGLEWPHWZICN-UHFFFAOYSA-N 5-(4-fluorophenyl)-4-phenyl-1h-pyrazolo[3,4-c]pyridazin-3-amine Chemical compound C=1C=CC=CC=1C1=C2C(N)=NNC2=NN=C1C1=CC=C(F)C=C1 JMAGLEWPHWZICN-UHFFFAOYSA-N 0.000 claims 4
- 102000015735 Beta-catenin Human genes 0.000 claims 4
- 108060000903 Beta-catenin Proteins 0.000 claims 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 4
- 229920002527 Glycogen Polymers 0.000 claims 4
- 230000015572 biosynthetic process Effects 0.000 claims 4
- 239000008103 glucose Substances 0.000 claims 4
- 229940096919 glycogen Drugs 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 230000026731 phosphorylation Effects 0.000 claims 4
- 238000006366 phosphorylation reaction Methods 0.000 claims 4
- 125000003107 substituted aryl group Chemical group 0.000 claims 4
- 238000003786 synthesis reaction Methods 0.000 claims 4
- -1 (3,4-dimethoxy-phenyl) -5-p-tolyl-1H-pyrazolo [3,4-c] pyridazin-3-ylamine Chemical compound 0.000 claims 3
- JHXDLIAMKPRADS-UHFFFAOYSA-N 4-(3-fluorophenyl)-5-phenyl-1h-pyrazolo[3,4-c]pyridazin-3-amine Chemical compound C=1C=CC(F)=CC=1C1=C2C(N)=NNC2=NN=C1C1=CC=CC=C1 JHXDLIAMKPRADS-UHFFFAOYSA-N 0.000 claims 3
- SEXDCZOTUATPCJ-UHFFFAOYSA-N 5-(3-fluorophenyl)-4-phenyl-1h-pyrazolo[3,4-c]pyridazin-3-amine Chemical compound C=1C=CC=CC=1C1=C2C(N)=NNC2=NN=C1C1=CC=CC(F)=C1 SEXDCZOTUATPCJ-UHFFFAOYSA-N 0.000 claims 3
- 230000036765 blood level Effects 0.000 claims 3
- AKNGRUGMIBUNNX-UHFFFAOYSA-N 3-(3-amino-4-phenyl-2h-pyrazolo[3,4-c]pyridazin-5-yl)benzamide Chemical compound NC(=O)C1=CC=CC(C=2C(=C3C(N)=NNC3=NN=2)C=2C=CC=CC=2)=C1 AKNGRUGMIBUNNX-UHFFFAOYSA-N 0.000 claims 2
- IDFNMLSYDALSTJ-UHFFFAOYSA-N 3-[3-amino-4-(2-methylphenyl)-2h-pyrazolo[3,4-c]pyridazin-5-yl]benzamide Chemical compound CC1=CC=CC=C1C1=C(C=2C=C(C=CC=2)C(N)=O)N=NC2=C1C(N)=NN2 IDFNMLSYDALSTJ-UHFFFAOYSA-N 0.000 claims 2
- JODDKWLYLYBWIZ-UHFFFAOYSA-N 3-[3-amino-5-(3-nitrophenyl)-1h-pyrazolo[3,4-c]pyridazin-4-yl]benzonitrile Chemical compound C=1C=CC(C#N)=CC=1C1=C2C(N)=NNC2=NN=C1C1=CC=CC([N+]([O-])=O)=C1 JODDKWLYLYBWIZ-UHFFFAOYSA-N 0.000 claims 2
- LQJWCMRWFCJIQE-UHFFFAOYSA-N 3-[3-amino-5-(3-phenoxyphenyl)-1h-pyrazolo[3,4-c]pyridazin-4-yl]benzonitrile Chemical compound C=1C=CC(C#N)=CC=1C1=C2C(N)=NNC2=NN=C1C(C=1)=CC=CC=1OC1=CC=CC=C1 LQJWCMRWFCJIQE-UHFFFAOYSA-N 0.000 claims 2
- AFUYIFQOSMYFMM-UHFFFAOYSA-N 4-(2,6-difluorophenyl)-5-(3-methoxyphenyl)-1h-pyrazolo[3,4-c]pyridazin-3-amine Chemical compound COC1=CC=CC(C=2C(=C3C(N)=NNC3=NN=2)C=2C(=CC=CC=2F)F)=C1 AFUYIFQOSMYFMM-UHFFFAOYSA-N 0.000 claims 2
- XBVVEHAQBBQDGO-UHFFFAOYSA-N 4-(2-methylphenyl)-5-(3-nitrophenyl)-2h-pyrazolo[3,4-c]pyridazin-3-amine Chemical compound CC1=CC=CC=C1C1=C(C=2C=C(C=CC=2)[N+]([O-])=O)N=NC2=C1C(N)=NN2 XBVVEHAQBBQDGO-UHFFFAOYSA-N 0.000 claims 2
- XTGMKRNEWFOUIR-UHFFFAOYSA-N 4-(2-methylphenyl)-5-(3-phenoxyphenyl)-2h-pyrazolo[3,4-c]pyridazin-3-amine Chemical compound CC1=CC=CC=C1C1=C(C=2C=C(OC=3C=CC=CC=3)C=CC=2)N=NC2=C1C(N)=NN2 XTGMKRNEWFOUIR-UHFFFAOYSA-N 0.000 claims 2
- LVEJQOZXZPSRLV-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(3-methylphenyl)-2h-pyrazolo[3,4-c]pyridazin-3-amine Chemical compound CC1=CC=CC(C=2C(=C3C(N)=NNC3=NN=2)C=2C=CC(Cl)=CC=2)=C1 LVEJQOZXZPSRLV-UHFFFAOYSA-N 0.000 claims 2
- AVDISOMQMOJXHY-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(3-phenoxyphenyl)-2h-pyrazolo[3,4-c]pyridazin-3-amine Chemical compound C=1C=C(Cl)C=CC=1C1=C2C(N)=NNC2=NN=C1C(C=1)=CC=CC=1OC1=CC=CC=C1 AVDISOMQMOJXHY-UHFFFAOYSA-N 0.000 claims 2
- FNXMBCWYAGWKSG-UHFFFAOYSA-N 4-[3-amino-4-(2-methylphenyl)-2h-pyrazolo[3,4-c]pyridazin-5-yl]benzamide Chemical compound CC1=CC=CC=C1C1=C(C=2C=CC(=CC=2)C(N)=O)N=NC2=C1C(N)=NN2 FNXMBCWYAGWKSG-UHFFFAOYSA-N 0.000 claims 2
- HSVROBQENKSWQY-UHFFFAOYSA-N 4-[3-amino-4-(3-methoxyphenyl)-2h-pyrazolo[3,4-c]pyridazin-5-yl]benzonitrile Chemical compound COC1=CC=CC(C=2C=3C(N)=NNC=3N=NC=2C=2C=CC(=CC=2)C#N)=C1 HSVROBQENKSWQY-UHFFFAOYSA-N 0.000 claims 2
- REFIMIGHWYMMPC-UHFFFAOYSA-N 4-[3-amino-5-(2-chlorophenyl)-1h-pyrazolo[3,4-c]pyridazin-4-yl]benzonitrile Chemical compound C=1C=C(C#N)C=CC=1C1=C2C(N)=NNC2=NN=C1C1=CC=CC=C1Cl REFIMIGHWYMMPC-UHFFFAOYSA-N 0.000 claims 2
- JWVJFQWLTBIMEV-UHFFFAOYSA-N 4-phenyl-5-pyridin-4-yl-1h-pyrazolo[3,4-c]pyridazin-3-amine Chemical compound C=1C=CC=CC=1C1=C2C(N)=NNC2=NN=C1C1=CC=NC=C1 JWVJFQWLTBIMEV-UHFFFAOYSA-N 0.000 claims 2
- BCTNHAUKHDCNGB-UHFFFAOYSA-N 5-(1,3-benzodioxol-5-yl)-4-(4-chlorophenyl)-1h-pyrazolo[3,4-c]pyridazin-3-amine Chemical compound C=12C(N)=NNC2=NN=C(C=2C=C3OCOC3=CC=2)C=1C1=CC=C(Cl)C=C1 BCTNHAUKHDCNGB-UHFFFAOYSA-N 0.000 claims 2
- LLWXDAQULUCWDC-UHFFFAOYSA-N 5-(1,3-benzodioxol-5-yl)-4-phenyl-1h-pyrazolo[3,4-c]pyridazin-3-amine Chemical compound C=12C(N)=NNC2=NN=C(C=2C=C3OCOC3=CC=2)C=1C1=CC=CC=C1 LLWXDAQULUCWDC-UHFFFAOYSA-N 0.000 claims 2
- YYGUSAHCDWSGJE-UHFFFAOYSA-N 5-(3-chlorophenyl)-4-phenyl-1h-pyrazolo[3,4-c]pyridazin-3-amine Chemical compound C=1C=CC=CC=1C1=C2C(N)=NNC2=NN=C1C1=CC=CC(Cl)=C1 YYGUSAHCDWSGJE-UHFFFAOYSA-N 0.000 claims 2
- BNMDZRIGIQLJGI-UHFFFAOYSA-N 5-(3-nitrophenyl)-4-phenyl-1h-pyrazolo[3,4-c]pyridazin-3-amine Chemical compound C=1C=CC=CC=1C1=C2C(N)=NNC2=NN=C1C1=CC=CC([N+]([O-])=O)=C1 BNMDZRIGIQLJGI-UHFFFAOYSA-N 0.000 claims 2
- YTBPMMBYXWEXTC-UHFFFAOYSA-N 5-(3-phenoxyphenyl)-4-phenyl-2h-pyrazolo[3,4-c]pyridazin-3-amine Chemical compound C=1C=CC=CC=1C1=C2C(N)=NNC2=NN=C1C(C=1)=CC=CC=1OC1=CC=CC=C1 YTBPMMBYXWEXTC-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 239000012472 biological sample Substances 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 230000006951 hyperphosphorylation Effects 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 claims 1
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 claims 1
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 claims 1
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 claims 1
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 claims 1
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 claims 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 claims 1
- GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 claims 1
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 claims 1
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 claims 1
- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 claims 1
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 claims 1
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 claims 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 claims 1
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 claims 1
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 claims 1
- OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 claims 1
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 claims 1
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 claims 1
- OMBVEVHRIQULKW-DNQXCXABSA-M (3r,5r)-7-[3-(4-fluorophenyl)-8-oxo-7-phenyl-1-propan-2-yl-5,6-dihydro-4h-pyrrolo[2,3-c]azepin-2-yl]-3,5-dihydroxyheptanoate Chemical compound O=C1C=2N(C(C)C)C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C=3C=CC(F)=CC=3)C=2CCCN1C1=CC=CC=C1 OMBVEVHRIQULKW-DNQXCXABSA-M 0.000 claims 1
- YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 claims 1
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| MXPA04007697A (es) * | 2002-02-06 | 2004-11-10 | Vertex Pharma | Compuestos de heteroarilo utiles como inhibidores de gsk-3. |
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| BRPI0415185A (pt) * | 2003-10-10 | 2006-11-28 | Pfizer Prod Inc | 2h-[1,2,4]triazol[4,3-a]pirazinas substituìdas como inibidores da gsk-3 |
| US20070043509A1 (en) * | 2003-11-03 | 2007-02-22 | Carter Daniel C | Albumin binding sites for evaluating drug interactions and methods of evaluating or designing drugs based on their albumin binding properties |
| EP1723427A2 (en) * | 2004-02-26 | 2006-11-22 | Bayer HealthCare AG | Diagnostics and therapeutics for diseases associated with glycogen synthase kinase 3 beta (gsk3b) |
| DE602005013670D1 (de) * | 2004-05-21 | 2009-05-14 | Inst Systems Biology | Zusammensetzungen und verfahren zur quantifizierung von serumglykoproteinen |
| MX2007005120A (es) | 2004-10-29 | 2007-07-16 | Abbott Lab | Nuevos inhibidores de cinasa. |
| WO2009126335A2 (en) * | 2008-04-08 | 2009-10-15 | University Of Florida Research Foundation, Inc. | Ant2 inhibitor compounds and methods of use thereof |
| US20100016247A1 (en) * | 2008-07-21 | 2010-01-21 | Florida State University Research Foundation | Using budding yeast to screen for inhibitors of aurora kinases |
| WO2010014253A2 (en) * | 2008-08-01 | 2010-02-04 | University Of Florida Research Foundation, Inc. | Ant4 inhibitor compounds and methods of use thereof |
| US8492344B2 (en) * | 2008-09-02 | 2013-07-23 | University Of Florida Research Foundation | PDK inhibitor compounds and methods of use thereof |
| WO2010075551A1 (en) * | 2008-12-24 | 2010-07-01 | Massachusetts Institute Of Technology | Compositions of modulators of the wnt/beta-catenin pathway and benzamide and/or hydroxamic acid derivatives to treat bipolar disorder |
| WO2011019648A1 (en) * | 2009-08-10 | 2011-02-17 | Epitherix, Llc | Indazoles as wnt/b-catenin signaling pathway inhibitors and therapeutic uses thereof |
| ES2835553T3 (es) | 2009-08-10 | 2021-06-22 | Biosplice Therapeutics Inc | Inhibidores de indazol de la vía de señalización de Wnt y sus usos terapéuticos |
| EP2464647B1 (en) | 2009-08-11 | 2016-09-21 | Bristol-Myers Squibb Company | Azaindazoles as btk kinase modulators and use thereof |
| CN102821607B (zh) * | 2009-12-21 | 2014-12-17 | 萨穆梅德有限公司 | 1H-吡唑并[3，4-b]吡啶及其治疗应用 |
| SI3311666T1 (sl) | 2010-08-18 | 2021-09-30 | Biosplice Therapeutics, Inc. | Diketoni in hidroksiketoni, kot aktivatorji signalne poti katenina |
| EP2701510B1 (en) | 2011-04-25 | 2017-02-15 | Usher III Initiative | Pyrazolopyridazines and methods for treating retinal-degenerative diseases and hearing loss associated with usher syndrome |
| US20130018026A1 (en) | 2011-07-14 | 2013-01-17 | Latham Keith R | Halogenated phenols for diagnostics, antioxidant protection and drug delivery |
| HRP20190281T1 (hr) | 2011-09-14 | 2019-05-31 | Samumed, Llc | Indazol-3-karboksamidi i njihova uporaba kao inhibitora signalizacijskog puta wnt/b-katenin |
| EP2825886A4 (en) * | 2012-03-14 | 2015-11-18 | Stephen Marx | MEDIUM AND METHODS OF DIAGNOSIS AND THERAPY OF ILLNESSES |
| PH12017500997A1 (en) | 2012-04-04 | 2018-02-19 | Samumed Llc | Indazole inhibitors of the wnt signal pathway and therapeutic uses thereof |
| PL2770994T3 (pl) | 2012-05-04 | 2020-03-31 | Samumed, Llc | 1H-Pirazolo[3,4-b]pirydyny i ich zastosowania terapeutyczne |
| US8765762B2 (en) | 2012-10-25 | 2014-07-01 | Usher III, Initiative, Inc. | Pyrazolopyridazines and methods for treating retinal-degerative diseases and hearing loss associated with usher syndrome |
| US9227976B2 (en) | 2012-10-25 | 2016-01-05 | Usher Iii Initiative, Inc. | Pyrazolopyridazines and methods for treating retinal-degenerative diseases and hearing loss associated with usher syndrome |
| PL2912038T3 (pl) * | 2012-10-25 | 2019-02-28 | Usher Iii Initiative, Inc. | Pirazolopirydazyny oraz sposoby leczenia zwyrodnieniowych chorób siatkówki i utraty słuchu związanych z zespołem ushera |
| EP2943198B1 (en) | 2013-01-08 | 2019-07-17 | Samumed, LLC | 3-(benzoimidazol-2-yl)-indazole inhibitors of the wnt signaling pathway and therapeutic uses thereof |
| PL2968249T3 (pl) | 2013-02-22 | 2019-06-28 | Samumed, Llc | Gamma-diketony jako aktywatory szlaku sygnałowego Wnt/beta-kateniny |
| CA2945263A1 (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 |
| RS59797B1 (sr) | 2014-08-20 | 2020-02-28 | Samumed Llc | Gama-diketoni za tretman i prevenciju starenja kože i bora |
| WO2016040188A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(3h-imidazo[4,5-c]pyridin-2-yl)-1h-pyrazolo[3,4-c]pyridine and therapeutic uses thereof |
| WO2016040181A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(1h-imidazo[4,5-c]pyridin-2-yl)-1h-pyrazolo[3,4-c]pyridine and therapeutic uses thereof |
| WO2016040185A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 2-(1h-indazol-3-yl)-3h-imidazo[4,5-b]pyridine and therapeutic uses thereof |
| WO2016040180A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(1h-benzo[d]imidazol-2-yl)-1h-pyrazolo[3,4-c]pyridine and therapeutic uses thereof |
| WO2016040182A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 2-(1h-indazol-3-yl)-1h-imidazo[4,5-c]pyridine and therapeutic uses thereof |
| WO2016040193A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(1h-imidazo[4,5-c]pyridin-2-yl)-1h-pyrazolo[3,4-b]pyridine and therapeutic uses thereof |
| WO2016040190A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(3h-imidazo[4,5-b]pyridin-2-yl)-1h-pyrazolo[3,4-b]pyridine and therapeutic uses thereof |
| WO2016040184A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(3h-imidazo[4,5-b]pyridin-2-yl)-1h-pyrazolo[3,4-c]pyridine and therapeutic uses thereof |
| WO2017024010A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-pyrrolo[3,2-c]pyridin-2-yl)-1h-indazoles and therapeutic uses thereof |
| WO2017024015A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(3h-imidazo[4,5-b]pyridin-2-yl)-1h-pyrazolo[4,3-b]pyridines and therapeutic uses thereof |
| WO2017023993A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-indol-2-yl)-1h-pyrazolo[4,3-b]pyridines and therapeutic uses thereof |
| WO2017023986A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc | 3-(1h-indol-2-yl)-1h-indazoles and therapeutic uses thereof |
| US10350199B2 (en) | 2015-08-03 | 2019-07-16 | Samumed, Llc | 3-(1h-pyrrolo[2,3-b]pyridin-2-yl)-1h-indazoles and therapeutic uses thereof |
| US10188634B2 (en) | 2015-08-03 | 2019-01-29 | Samumed, Llc | 3-(3H-imidazo[4,5-C]pyridin-2-yl)-1 H-pyrazolo[4,3-B]pyridines and therapeutic uses thereof |
| WO2017023972A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-imidazo[4,5-c]pyridin-2-yl)-1h-pyrazolo[4,3-b]pyridines and therapeutic uses thereof |
| US10285983B2 (en) | 2015-08-03 | 2019-05-14 | Samumed, Llc | 3-(1H-pyrrolo[2,3-B]pyridin-2-yl)-1H-pyrazolo[3,4-B] pyridines and therapeutic uses thereof |
| US10231956B2 (en) | 2015-08-03 | 2019-03-19 | Samumed, Llc | 3-(1H-pyrrolo[3,2-C]pyridin-2-YL)-1 H-pyrazolo[4,3-B]pyridines and therapeutic uses thereof |
| US10519169B2 (en) | 2015-08-03 | 2019-12-31 | Samumed, Llc | 3-(1H-pyrrolo[2,3-C]pyridin-2-yl)-1 H-pyrazolo[4,3-B]pyridines and therapeutic uses thereof |
| US10206909B2 (en) | 2015-08-03 | 2019-02-19 | Samumed, Llc | 3-(1H-pyrrolo[2,3-B]pyridin-2-yl)-1H-pyrazolo[4,3-B]pyridines and therapeutic uses thereof |
| US10285982B2 (en) | 2015-08-03 | 2019-05-14 | Samumed, Llc | 3-(1H-pyrrolo[2,3-B]pyridin-2-yl)-1H-pyrazolo[3,4-C]pyridines and therapeutic uses thereof |
| US10166218B2 (en) | 2015-08-03 | 2019-01-01 | Samumed, Llc | 3-(1H-indol-2-yl)-1H-pyrazolo[3,4-C]pyridines and therapeutic uses thereof |
| WO2017023984A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-pyrrolo[3,2-c]pyridin-2-yl)-1h-pyrazolo[3,4-c]pyridines and therapeutic uses thereof |
| WO2017023987A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-pyrrolo[3,2-c]pyridin-2-yl)-1h-pyrazolo[3,4-b]pyridines and therapeutic uses thereof |
| US10392383B2 (en) | 2015-08-03 | 2019-08-27 | Samumed, Llc | 3-(1H-benzo[d]imidazol-2-yl)-1H-pyrazolo[4,3-b]pyridines and therapeutic uses thereof |
| WO2017023975A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-pyrrolo[2,3-c]pyridin-2-yl)-1h-pyrazolo[3,4-c]pyridines and therapeutic uses thereof |
| EP3341397B1 (en) * | 2015-08-25 | 2024-12-18 | Histide AG | Compounds for inducing tissue formation and uses thereof |
| WO2017032857A2 (en) * | 2015-08-25 | 2017-03-02 | Histide Ag | Compounds for inducing tissue formation and uses thereof |
| WO2017032856A2 (en) * | 2015-08-25 | 2017-03-02 | Histide Ag | Compounds for inducing tissue formation and uses thereof |
| KR20180080262A (ko) | 2015-11-06 | 2018-07-11 | 사뮤메드, 엘엘씨 | 골관절염의 치료 |
| ES2933109T3 (es) | 2016-06-01 | 2023-02-02 | Biosplice Therapeutics Inc | Proceso para preparar N-(5-(3-(7-(3-fluorofenil)-3h-imidazo[4,5-c]piridin-2-il)-1h-indazol-5-il)piridin-3-il)-3-metilbutanamida |
| CN110709082A (zh) | 2016-10-21 | 2020-01-17 | 萨穆梅德有限公司 | 吲唑-3-甲酰胺的使用方法及其作为Wnt/β-连环蛋白信号传导途径抑制剂的用途 |
| KR102558716B1 (ko) | 2016-11-07 | 2023-07-21 | 사뮤메드, 엘엘씨 | 단일-투여량, 즉시-사용가능한 주사용 제제 |
| CN110914265B (zh) * | 2017-05-15 | 2022-12-23 | 密歇根大学董事会 | 作为lsd-1抑制剂的吡咯并[2,3-c]吡啶和相关类似物 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4009022A (en) | 1975-10-30 | 1977-02-22 | Rohm And Haas Company | Selective antagonists for triazine herbicides |
| US4886646A (en) | 1988-03-23 | 1989-12-12 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Hanging drop crystal growth apparatus and method |
| US5096676A (en) | 1989-01-27 | 1992-03-17 | Mcpherson Alexander | Crystal growing apparatus |
| US5130105A (en) * | 1990-10-23 | 1992-07-14 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Protein crystal growth tray assembly |
| US5200910A (en) | 1991-01-30 | 1993-04-06 | The Board Of Trustees Of The Leland Stanford University | Method for modelling the electron density of a crystal |
| AU3320193A (en) | 1991-07-22 | 1993-02-23 | Regents Of The University Of California, The | Methods of designing specific affectors using three-dimensional conformation of enzyme/affector complex |
| US5221410A (en) * | 1991-10-09 | 1993-06-22 | Schering Corporation | Crystal forming device |
| US5353236A (en) * | 1992-04-23 | 1994-10-04 | The Board Of Trustees Of The Leland Stanford University | High-resolution crystallographic modelling of a macromolecule |
| US5453937A (en) | 1993-04-28 | 1995-09-26 | Immunex Corporation | Method and system for protein modeling |
| US5400741A (en) | 1993-05-21 | 1995-03-28 | Medical Foundation Of Buffalo, Inc. | Device for growing crystals |
| CA2279846C (en) | 1997-02-07 | 2008-06-03 | Princeton University | Engineered protein kinases which can utilize modified nucleotide triphosphate substrates |
| GB9721437D0 (en) * | 1997-10-10 | 1997-12-10 | Glaxo Group Ltd | Heteroaromatic compounds and their use in medicine |
| US6162613A (en) * | 1998-02-18 | 2000-12-19 | Vertex Pharmaceuticals, Inc. | Methods for designing inhibitors of serine/threonine-kinases and tyrosine kinases |
| ATE274510T1 (de) | 1998-06-19 | 2004-09-15 | Chiron Corp | Glycogen synthase kinase 3 inhibitoren |
| US6184226B1 (en) | 1998-08-28 | 2001-02-06 | Scios Inc. | Quinazoline derivatives as inhibitors of P-38 α |
| US6387641B1 (en) * | 1998-12-16 | 2002-05-14 | Vertex Pharmaceuticals Incorporated | Crystallized P38 complexes |
| GB9828640D0 (en) | 1998-12-23 | 1999-02-17 | Smithkline Beecham Plc | Novel method and compounds |
| JP4122216B2 (ja) * | 2000-09-19 | 2008-07-23 | ノバルティス バクシンズ アンド ダイアグノスティックス，インコーポレーテッド | ＧＳＫ−３βタンパク質の特徴づけおよびその使用方法 |
| EP1319001A1 (en) * | 2000-09-22 | 2003-06-18 | Smithkline Beecham Plc | Pyrazolopyridines and pyrazolopyridazines as antidiabetics |
| WO2002050254A2 (en) * | 2000-12-18 | 2002-06-27 | Smithkline Beecham P.L.C. | Crystal structure of glycogen synthase kinase 3 beta |
| JP2005532265A (ja) * | 2002-02-11 | 2005-10-27 | カイロン コーポレイション | ヒトｇｓｋ３を結晶化するための方法およびその新規な結晶構造 |
| GB0206723D0 (en) * | 2002-03-21 | 2002-05-01 | Glaxo Group Ltd | Novel compounds |
-
2002
- 2002-04-29 US US10/135,255 patent/US7390808B2/en not_active Expired - Fee Related
- 2002-04-29 AU AU2002259071A patent/AU2002259071A1/en not_active Abandoned
- 2002-04-29 EP EP10011814A patent/EP2295550A3/en not_active Withdrawn
- 2002-04-29 AT AT02729056T patent/ATE433751T1/de not_active IP Right Cessation
- 2002-04-29 CA CA002444882A patent/CA2444882A1/en not_active Abandoned
- 2002-04-29 DE DE60232669T patent/DE60232669D1/de not_active Expired - Lifetime
- 2002-04-29 MX MXPA03009957A patent/MXPA03009957A/es not_active Application Discontinuation
- 2002-04-29 EP EP02729056A patent/EP1435957B1/en not_active Expired - Lifetime
- 2002-04-29 JP JP2002585380A patent/JP2005504731A/ja not_active Withdrawn
- 2002-04-29 WO PCT/US2002/013511 patent/WO2002088078A2/en not_active Ceased
- 2002-04-29 EP EP09004787A patent/EP2082743A3/en not_active Withdrawn
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2008
- 2008-03-28 US US12/079,917 patent/US7666647B2/en not_active Expired - Fee Related
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2009
- 2009-09-30 JP JP2009229078A patent/JP2010059162A/ja active Pending
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2010
- 2010-01-05 US US12/652,152 patent/US7883881B2/en not_active Expired - Fee Related
- 2010-11-12 US US12/944,909 patent/US8318467B2/en not_active Expired - Fee Related
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