CA2689117A1 - 5-heteroaryl substituted indazoles as kinase inhibitors - Google Patents
5-heteroaryl substituted indazoles as kinase inhibitors Download PDFInfo
- Publication number
- CA2689117A1 CA2689117A1 CA002689117A CA2689117A CA2689117A1 CA 2689117 A1 CA2689117 A1 CA 2689117A1 CA 002689117 A CA002689117 A CA 002689117A CA 2689117 A CA2689117 A CA 2689117A CA 2689117 A1 CA2689117 A1 CA 2689117A1
- Authority
- CA
- Canada
- Prior art keywords
- indazol
- triazol
- benzyl
- carboxamide
- indazole
- 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.)
- Abandoned
Links
- 150000002473 indoazoles Chemical class 0.000 title 1
- 229940043355 kinase inhibitor Drugs 0.000 title 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 468
- 238000000034 method Methods 0.000 claims abstract description 262
- 102000001267 GSK3 Human genes 0.000 claims abstract description 95
- 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 claims abstract description 95
- 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 26
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 26
- 102000020233 phosphotransferase Human genes 0.000 claims abstract description 26
- 108010024121 Janus Kinases Proteins 0.000 claims abstract description 21
- 102000015617 Janus Kinases Human genes 0.000 claims abstract description 21
- 239000011435 rock Substances 0.000 claims abstract description 15
- 102000000568 rho-Associated Kinases Human genes 0.000 claims abstract description 4
- 108010041788 rho-Associated Kinases Proteins 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- 101000987297 Homo sapiens Serine/threonine-protein kinase PAK 4 Proteins 0.000 claims abstract description 3
- 102100027940 Serine/threonine-protein kinase PAK 4 Human genes 0.000 claims abstract description 3
- 101001001642 Xenopus laevis Serine/threonine-protein kinase pim-3 Proteins 0.000 claims abstract description 3
- 239000005441 aurora Substances 0.000 claims abstract description 3
- 101000950695 Homo sapiens Mitogen-activated protein kinase 8 Proteins 0.000 claims abstract 2
- 102100037808 Mitogen-activated protein kinase 8 Human genes 0.000 claims abstract 2
- -1 R j R k N-alkyl- Chemical group 0.000 claims description 167
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 145
- 239000001257 hydrogen Substances 0.000 claims description 144
- 125000000217 alkyl group Chemical group 0.000 claims description 125
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- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 10
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- 230000002159 abnormal effect Effects 0.000 claims description 9
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 9
- GVMDVMPNOAVKJR-UHFFFAOYSA-N 5-(1-benzyltriazol-4-yl)-1h-indazole Chemical compound C1=C(C=2C=C3C=NNC3=CC=2)N=NN1CC1=CC=CC=C1 GVMDVMPNOAVKJR-UHFFFAOYSA-N 0.000 claims description 8
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- LFJAFAATTGXWLI-UHFFFAOYSA-N 1-[3-[5-(3-amino-1h-indazol-5-yl)-3-benzyltriazol-4-yl]phenyl]-3-(3-methylphenyl)urea Chemical compound CC1=CC=CC(NC(=O)NC=2C=C(C=CC=2)C=2N(N=NC=2C=2C=C3C(N)=NNC3=CC=2)CC=2C=CC=CC=2)=C1 LFJAFAATTGXWLI-UHFFFAOYSA-N 0.000 claims description 4
- VUWOSKCPLJROAK-UHFFFAOYSA-N 3,5-bis(1-benzyltriazol-4-yl)-1h-indazole Chemical compound C1=C(C=2C3=CC(=CC=C3NN=2)C=2N=NN(CC=3C=CC=CC=3)C=2)N=NN1CC1=CC=CC=C1 VUWOSKCPLJROAK-UHFFFAOYSA-N 0.000 claims description 4
- CTJAMSGCMYAVCZ-UHFFFAOYSA-N 4-(1h-indazol-5-yl)-n-phenyl-1,3-thiazol-2-amine Chemical compound N=1C(C=2C=C3C=NNC3=CC=2)=CSC=1NC1=CC=CC=C1 CTJAMSGCMYAVCZ-UHFFFAOYSA-N 0.000 claims description 4
- UOOFSEUSROQBBP-UHFFFAOYSA-N 5-(1-benzyl-5-cyclopropyltriazol-4-yl)-1h-indazol-3-amine Chemical compound C1=C2C(N)=NNC2=CC=C1C(=C1C2CC2)N=NN1CC1=CC=CC=C1 UOOFSEUSROQBBP-UHFFFAOYSA-N 0.000 claims description 4
- JXMYIDZREHNPDO-UHFFFAOYSA-N 5-(1-benzyl-5-cyclopropyltriazol-4-yl)-1h-indazole Chemical compound N1=NC(C=2C=C3C=NNC3=CC=2)=C(C2CC2)N1CC1=CC=CC=C1 JXMYIDZREHNPDO-UHFFFAOYSA-N 0.000 claims description 4
- AOBLBPWPSKBHSI-UHFFFAOYSA-N 5-(1-benzyl-5-iodotriazol-4-yl)-1h-indazol-3-amine Chemical compound C1=C2C(N)=NNC2=CC=C1C(=C1I)N=NN1CC1=CC=CC=C1 AOBLBPWPSKBHSI-UHFFFAOYSA-N 0.000 claims description 4
- UTFXYGYVDDLJER-UHFFFAOYSA-N 5-(1-benzyl-5-methyltriazol-4-yl)-1h-indazol-3-amine Chemical compound CC1=C(C=2C=C3C(N)=NNC3=CC=2)N=NN1CC1=CC=CC=C1 UTFXYGYVDDLJER-UHFFFAOYSA-N 0.000 claims description 4
- UYVFHXXGQCYYCU-UHFFFAOYSA-N 5-(1-benzyl-5-methyltriazol-4-yl)-1h-indazole Chemical compound CC1=C(C=2C=C3C=NNC3=CC=2)N=NN1CC1=CC=CC=C1 UYVFHXXGQCYYCU-UHFFFAOYSA-N 0.000 claims description 4
- XSDJOIOVIMPMHD-UHFFFAOYSA-N 5-(1-benzyl-5-phenyltriazol-4-yl)-1h-indazol-3-amine Chemical compound C1=C2C(N)=NNC2=CC=C1C(=C1C=2C=CC=CC=2)N=NN1CC1=CC=CC=C1 XSDJOIOVIMPMHD-UHFFFAOYSA-N 0.000 claims description 4
- IOYGZJJCJBOPDM-UHFFFAOYSA-N 5-(1-benzyl-5-phenyltriazol-4-yl)-1h-indazole Chemical compound N1=NC(C=2C=C3C=NNC3=CC=2)=C(C=2C=CC=CC=2)N1CC1=CC=CC=C1 IOYGZJJCJBOPDM-UHFFFAOYSA-N 0.000 claims description 4
- AGYZUONRISUOIK-UHFFFAOYSA-N 5-(1-benzyltriazol-4-yl)-3-phenyl-1h-indazole Chemical compound C1=C(C=2C=C3C(C=4C=CC=CC=4)=NNC3=CC=2)N=NN1CC1=CC=CC=C1 AGYZUONRISUOIK-UHFFFAOYSA-N 0.000 claims description 4
- PYWUGDQVHDHKLX-UHFFFAOYSA-N 5-(1h-indazol-5-yl)-n-methyl-1,2-oxazole-3-carboxamide Chemical compound O1N=C(C(=O)NC)C=C1C1=CC=C(NN=C2)C2=C1 PYWUGDQVHDHKLX-UHFFFAOYSA-N 0.000 claims description 4
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- FQEODTMNWMDUMD-UHFFFAOYSA-N 5-[3-(2-methylpropyl)-1,2-oxazol-5-yl]-1h-indazol-3-amine Chemical compound O1N=C(CC(C)C)C=C1C1=CC=C(NN=C2N)C2=C1 FQEODTMNWMDUMD-UHFFFAOYSA-N 0.000 claims description 4
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- ZVZCNOQSOULQEK-UHFFFAOYSA-N [5-(1h-indazol-5-yl)-1,2-oxazol-3-yl]-piperidin-1-ylmethanone Chemical compound C1=C(C=2C=C3C=NNC3=CC=2)ON=C1C(=O)N1CCCCC1 ZVZCNOQSOULQEK-UHFFFAOYSA-N 0.000 claims description 4
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- YJSIMMVEIYLSHC-UHFFFAOYSA-N n-benzyl-4-(1h-indazol-5-yl)-5-phenyl-1,3-thiazol-2-amine Chemical compound C=1C=CC=CC=1CNC(S1)=NC(C=2C=C3C=NNC3=CC=2)=C1C1=CC=CC=C1 YJSIMMVEIYLSHC-UHFFFAOYSA-N 0.000 claims description 4
- HENXDAXZQIPSPS-UHFFFAOYSA-N n-cyclohexyl-6-(1h-indazol-5-yl)imidazo[2,1-b][1,3]thiazol-5-amine Chemical compound C1CCCCC1NC1=C(C=2C=C3C=NNC3=CC=2)N=C2N1C=CS2 HENXDAXZQIPSPS-UHFFFAOYSA-N 0.000 claims description 4
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- ZTUKHYNMEWPBNZ-UHFFFAOYSA-N 5-(1h-indazol-5-yl)-3-(piperidin-1-ylmethyl)-1,2-oxazole Chemical compound C1=C(C=2C=C3C=NNC3=CC=2)ON=C1CN1CCCCC1 ZTUKHYNMEWPBNZ-UHFFFAOYSA-N 0.000 claims description 3
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- AKADPZBTZLFVEZ-UHFFFAOYSA-N 5-[3-benzyl-5-(4-fluorophenyl)imidazol-4-yl]-1h-indazole Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=C3C=NNC3=CC=2)N(CC=2C=CC=CC=2)C=N1 AKADPZBTZLFVEZ-UHFFFAOYSA-N 0.000 claims description 3
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- KZZVBKVGYMMMIZ-UHFFFAOYSA-N 5-[5-(4-fluorophenyl)-3-[2-(1-methylpyrrolidin-2-yl)ethyl]imidazol-4-yl]-1h-indazole Chemical compound CN1CCCC1CCN1C(C=2C=C3C=NNC3=CC=2)=C(C=2C=CC(F)=CC=2)N=C1 KZZVBKVGYMMMIZ-UHFFFAOYSA-N 0.000 claims description 3
- HODXDVJXGUEBPT-UHFFFAOYSA-N 5-[5-(4-fluorophenyl)-3-[2-(4-methylpiperidin-1-yl)ethyl]imidazol-4-yl]-1h-indazole Chemical compound C1CC(C)CCN1CCN1C(C=2C=C3C=NNC3=CC=2)=C(C=2C=CC(F)=CC=2)N=C1 HODXDVJXGUEBPT-UHFFFAOYSA-N 0.000 claims description 3
- AJIYAKYSKXQNCQ-UHFFFAOYSA-N 5-[5-(4-fluorophenyl)-3-[3-(4-methylpiperazin-1-yl)propyl]imidazol-4-yl]-1h-indazole Chemical compound C1CN(C)CCN1CCCN1C(C=2C=C3C=NNC3=CC=2)=C(C=2C=CC(F)=CC=2)N=C1 AJIYAKYSKXQNCQ-UHFFFAOYSA-N 0.000 claims description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 3
- GNZPMJDEUIVORU-GFCCVEGCSA-N [(3r)-3-hydroxypiperidin-1-yl]-[5-(1h-indazol-5-yl)-1,2-oxazol-3-yl]methanone Chemical compound C1[C@H](O)CCCN1C(=O)C1=NOC(C=2C=C3C=NNC3=CC=2)=C1 GNZPMJDEUIVORU-GFCCVEGCSA-N 0.000 claims description 3
- HWGZXYUOXGVACR-UHFFFAOYSA-N [3-amino-5-(1-benzyltriazol-4-yl)indazol-1-yl]-(1-methylpiperidin-4-yl)methanone Chemical compound C1CN(C)CCC1C(=O)N1C2=CC=C(C=3N=NN(CC=4C=CC=CC=4)C=3)C=C2C(N)=N1 HWGZXYUOXGVACR-UHFFFAOYSA-N 0.000 claims description 3
- MCQYVXXUIQXRTH-UHFFFAOYSA-N [4-[2-(2-hydroxyethoxy)ethyl]piperazin-1-yl]-[5-(1h-indazol-5-yl)-1,2-oxazol-3-yl]methanone Chemical compound C1CN(CCOCCO)CCN1C(=O)C1=NOC(C=2C=C3C=NNC3=CC=2)=C1 MCQYVXXUIQXRTH-UHFFFAOYSA-N 0.000 claims description 3
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- WHYJJQGVJCOSBN-UHFFFAOYSA-N 5-[5-(4-fluorophenyl)-3-piperidin-4-ylimidazol-4-yl]-1h-indazole Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=C3C=NNC3=CC=2)N(C2CCNCC2)C=N1 WHYJJQGVJCOSBN-UHFFFAOYSA-N 0.000 claims description 2
- CPXRUHVJQDYEJU-UHFFFAOYSA-N 5-[5-cyclopropyl-1-(oxan-4-ylmethyl)triazol-4-yl]-1h-indazole Chemical compound N1=NC(C=2C=C3C=NNC3=CC=2)=C(C2CC2)N1CC1CCOCC1 CPXRUHVJQDYEJU-UHFFFAOYSA-N 0.000 claims description 2
- KFGBPPDTVSCUKQ-UHFFFAOYSA-N 5-imidazo[1,2-a]pyridin-3-yl-1h-indazol-3-amine Chemical compound C1=CC=CN2C(C3=CC=C4NN=C(C4=C3)N)=CN=C21 KFGBPPDTVSCUKQ-UHFFFAOYSA-N 0.000 claims description 2
- PQXZDCCZRQXJML-UHFFFAOYSA-N 5-pyrazin-2-yl-1h-indazol-3-amine Chemical compound C1=C2C(N)=NNC2=CC=C1C1=CN=CC=N1 PQXZDCCZRQXJML-UHFFFAOYSA-N 0.000 claims description 2
- FNWFDFRPNIDEFX-UHFFFAOYSA-N 5-thiophen-2-yl-1h-indazol-3-amine Chemical compound C1=C2C(N)=NNC2=CC=C1C1=CC=CS1 FNWFDFRPNIDEFX-UHFFFAOYSA-N 0.000 claims description 2
- IZSNWWGBQTUPOV-UHFFFAOYSA-N [3-amino-5-(1-benzyltriazol-4-yl)indazol-1-yl]-(1-methylpiperidin-2-yl)methanone Chemical compound CN1CCCCC1C(=O)N1C2=CC=C(C=3N=NN(CC=4C=CC=CC=4)C=3)C=C2C(N)=N1 IZSNWWGBQTUPOV-UHFFFAOYSA-N 0.000 claims description 2
- KTWAXVSMJRXRJR-UHFFFAOYSA-N [3-benzyl-5-(1h-indazol-5-yl)triazol-4-yl]-(2,6-dimethylmorpholin-4-yl)methanone Chemical compound C1C(C)OC(C)CN1C(=O)C1=C(C=2C=C3C=NNC3=CC=2)N=NN1CC1=CC=CC=C1 KTWAXVSMJRXRJR-UHFFFAOYSA-N 0.000 claims description 2
- OPEJZAYIBYIDHY-UHFFFAOYSA-N [3-benzyl-5-(1h-indazol-5-yl)triazol-4-yl]-(3-chlorophenyl)methanone Chemical compound ClC1=CC=CC(C(=O)C=2N(N=NC=2C=2C=C3C=NNC3=CC=2)CC=2C=CC=CC=2)=C1 OPEJZAYIBYIDHY-UHFFFAOYSA-N 0.000 claims description 2
- SSJZTZBXBGQNGK-UHFFFAOYSA-N [3-benzyl-5-(1h-indazol-5-yl)triazol-4-yl]-(4-hydroxypiperidin-1-yl)methanone Chemical compound C1CC(O)CCN1C(=O)C1=C(C=2C=C3C=NNC3=CC=2)N=NN1CC1=CC=CC=C1 SSJZTZBXBGQNGK-UHFFFAOYSA-N 0.000 claims description 2
- OSHNQBILLKPIDC-UHFFFAOYSA-N [3-benzyl-5-(1h-indazol-5-yl)triazol-4-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=C(C=2C=C3C=NNC3=CC=2)N=NN1CC1=CC=CC=C1 OSHNQBILLKPIDC-UHFFFAOYSA-N 0.000 claims description 2
- RTNQZCCYFMHHEN-UHFFFAOYSA-N [3-benzyl-5-(1h-indazol-5-yl)triazol-4-yl]-(4-phenylpiperazin-1-yl)methanone Chemical compound C=1C=C2NN=CC2=CC=1C=1N=NN(CC=2C=CC=CC=2)C=1C(=O)N(CC1)CCN1C1=CC=CC=C1 RTNQZCCYFMHHEN-UHFFFAOYSA-N 0.000 claims description 2
- BUFKVWVQPNNOJQ-GOSISDBHSA-N [3-benzyl-5-(1h-indazol-5-yl)triazol-4-yl]-[(3r)-3-hydroxypiperidin-1-yl]methanone Chemical compound C1[C@H](O)CCCN1C(=O)C1=C(C=2C=C3C=NNC3=CC=2)N=NN1CC1=CC=CC=C1 BUFKVWVQPNNOJQ-GOSISDBHSA-N 0.000 claims description 2
- LUDGJIGCNAUXKE-UHFFFAOYSA-N [3-benzyl-5-(1h-indazol-5-yl)triazol-4-yl]-cyclopropylmethanone Chemical compound C=1C=C2NN=CC2=CC=1C=1N=NN(CC=2C=CC=CC=2)C=1C(=O)C1CC1 LUDGJIGCNAUXKE-UHFFFAOYSA-N 0.000 claims description 2
- JIFKOKHSLOPKOQ-UHFFFAOYSA-N [3-benzyl-5-(1h-indazol-5-yl)triazol-4-yl]-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1=C(C=2C=C3C=NNC3=CC=2)N=NN1CC1=CC=CC=C1 JIFKOKHSLOPKOQ-UHFFFAOYSA-N 0.000 claims description 2
- QKILYTZWSKQLLU-UHFFFAOYSA-N [3-benzyl-5-(1h-indazol-5-yl)triazol-4-yl]-piperidin-1-ylmethanone Chemical compound C=1C=C2NN=CC2=CC=1C=1N=NN(CC=2C=CC=CC=2)C=1C(=O)N1CCCCC1 QKILYTZWSKQLLU-UHFFFAOYSA-N 0.000 claims description 2
- OSUXLDVAHXPXIW-UHFFFAOYSA-N [5-(1h-indazol-5-yl)-1,2-oxazol-3-yl]-(2-phenylpiperidin-1-yl)methanone Chemical compound C1=C(C=2C=C3C=NNC3=CC=2)ON=C1C(=O)N1CCCCC1C1=CC=CC=C1 OSUXLDVAHXPXIW-UHFFFAOYSA-N 0.000 claims description 2
- ZODGMGRCDFEGPD-UHFFFAOYSA-N [5-(1h-indazol-5-yl)-1,2-oxazol-3-yl]-(2-phenylpyrrolidin-1-yl)methanone Chemical compound C1=C(C=2C=C3C=NNC3=CC=2)ON=C1C(=O)N1CCCC1C1=CC=CC=C1 ZODGMGRCDFEGPD-UHFFFAOYSA-N 0.000 claims description 2
- SIZYTGIBDRZVJL-UHFFFAOYSA-N [5-(1h-indazol-5-yl)-1,2-oxazol-3-yl]-(3-phenylmorpholin-4-yl)methanone Chemical compound C1=C(C=2C=C3C=NNC3=CC=2)ON=C1C(=O)N1CCOCC1C1=CC=CC=C1 SIZYTGIBDRZVJL-UHFFFAOYSA-N 0.000 claims description 2
- QOFVKPKZWLBUJA-UHFFFAOYSA-N [5-(1h-indazol-5-yl)-1,2-oxazol-3-yl]-(3-phenylpyrrolidin-1-yl)methanone Chemical compound C1=C(C=2C=C3C=NNC3=CC=2)ON=C1C(=O)N(C1)CCC1C1=CC=CC=C1 QOFVKPKZWLBUJA-UHFFFAOYSA-N 0.000 claims description 2
- QQMYTHUROLXTJD-UHFFFAOYSA-N [5-(1h-indazol-5-yl)-1,2-oxazol-3-yl]-(4-methyl-1,4-diazepan-1-yl)methanone Chemical compound C1CN(C)CCCN1C(=O)C1=NOC(C=2C=C3C=NNC3=CC=2)=C1 QQMYTHUROLXTJD-UHFFFAOYSA-N 0.000 claims description 2
- DMBILIHTXKNZCJ-UHFFFAOYSA-N [5-(1h-indazol-5-yl)-1,2-oxazol-3-yl]-(4-methyl-2-phenylpiperazin-1-yl)methanone Chemical compound C1N(C)CCN(C(=O)C2=NOC(=C2)C=2C=C3C=NNC3=CC=2)C1C1=CC=CC=C1 DMBILIHTXKNZCJ-UHFFFAOYSA-N 0.000 claims description 2
- SNUFUWLUARRPOI-UHFFFAOYSA-N [5-(1h-indazol-5-yl)-3-(oxan-4-ylmethyl)triazol-4-yl]-(oxan-4-yl)methanone Chemical compound C=1C=C2NN=CC2=CC=1C=1N=NN(CC2CCOCC2)C=1C(=O)C1CCOCC1 SNUFUWLUARRPOI-UHFFFAOYSA-N 0.000 claims description 2
- HMKYTNQOYPRIIL-UHFFFAOYSA-N cyclopentyl-[5-(1h-indazol-5-yl)-3-(oxan-4-ylmethyl)triazol-4-yl]methanone Chemical compound C=1C=C2NN=CC2=CC=1C=1N=NN(CC2CCOCC2)C=1C(=O)C1CCCC1 HMKYTNQOYPRIIL-UHFFFAOYSA-N 0.000 claims description 2
- DZPUKFPQRIUXAV-UHFFFAOYSA-N ethyl 2-[4-[3-[[2-(dimethylamino)acetyl]amino]-1h-indazol-5-yl]triazol-1-yl]acetate Chemical compound N1=NN(CC(=O)OCC)C=C1C1=CC=C(NN=C2NC(=O)CN(C)C)C2=C1 DZPUKFPQRIUXAV-UHFFFAOYSA-N 0.000 claims description 2
- KZFZICKJGNNQJC-UHFFFAOYSA-N methyl 3-[4-(3-amino-1h-indazol-5-yl)pyrazol-1-yl]propanoate Chemical compound C1=NN(CCC(=O)OC)C=C1C1=CC=C(NN=C2N)C2=C1 KZFZICKJGNNQJC-UHFFFAOYSA-N 0.000 claims description 2
- DNOFVHLNUCBASP-UHFFFAOYSA-N methyl 3-[[4-(1h-indazol-5-yl)triazol-1-yl]methyl]benzoate Chemical compound COC(=O)C1=CC=CC(CN2N=NC(=C2)C=2C=C3C=NNC3=CC=2)=C1 DNOFVHLNUCBASP-UHFFFAOYSA-N 0.000 claims description 2
- JAGLRLYFXRNUEY-UHFFFAOYSA-N n,3-dibenzyl-5-(1h-indazol-5-yl)triazole-4-carboxamide Chemical compound C=1C=C2NN=CC2=CC=1C=1N=NN(CC=2C=CC=CC=2)C=1C(=O)NCC1=CC=CC=C1 JAGLRLYFXRNUEY-UHFFFAOYSA-N 0.000 claims description 2
- KEIZGXGINCGVRL-UHFFFAOYSA-N n,3-dibenzyl-n-(2-hydroxyethyl)-5-(1h-indazol-5-yl)triazole-4-carboxamide Chemical compound C=1C=C2NN=CC2=CC=1C=1N=NN(CC=2C=CC=CC=2)C=1C(=O)N(CCO)CC1=CC=CC=C1 KEIZGXGINCGVRL-UHFFFAOYSA-N 0.000 claims description 2
- VLMMUIFKJFEWLL-UHFFFAOYSA-N n,3-dibenzyl-n-ethyl-5-(1h-indazol-5-yl)triazole-4-carboxamide Chemical compound C=1C=C2NN=CC2=CC=1C=1N=NN(CC=2C=CC=CC=2)C=1C(=O)N(CC)CC1=CC=CC=C1 VLMMUIFKJFEWLL-UHFFFAOYSA-N 0.000 claims description 2
- KILOJIWDWVSWOX-UHFFFAOYSA-N n-(2,3-dihydro-1,4-benzodioxin-5-ylmethyl)-5-(1h-indazol-5-yl)-1,2-oxazole-3-carboxamide Chemical compound C1=C2NN=CC2=CC(C2=CC(=NO2)C(NCC=2C=3OCCOC=3C=CC=2)=O)=C1 KILOJIWDWVSWOX-UHFFFAOYSA-N 0.000 claims description 2
- BSWFQKXORDDMEH-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-1-yl)-5-(1h-indazol-5-yl)-1,2-oxazole-3-carboxamide Chemical compound C1=C2NN=CC2=CC(C2=CC(=NO2)C(NC2C3=CC=CC=C3CC2)=O)=C1 BSWFQKXORDDMEH-UHFFFAOYSA-N 0.000 claims description 2
- LPZBSMPSQIHFBU-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-5-(1h-indazol-5-yl)-1,2-oxazole-3-carboxamide Chemical compound C1=C2NN=CC2=CC(C2=CC(=NO2)C(NC2CC3=CC=CC=C3C2)=O)=C1 LPZBSMPSQIHFBU-UHFFFAOYSA-N 0.000 claims description 2
- AUTNKPCXFMABBR-UHFFFAOYSA-N n-(2-hydroxy-2-phenylethyl)-5-(1h-indazol-5-yl)-n-methyl-1,2-oxazole-3-carboxamide Chemical compound C1=C(C=2C=C3C=NNC3=CC=2)ON=C1C(=O)N(C)CC(O)C1=CC=CC=C1 AUTNKPCXFMABBR-UHFFFAOYSA-N 0.000 claims description 2
- GKVMBHXCXNESJY-UHFFFAOYSA-N n-(2-imidazol-1-yl-1-phenylethyl)-5-(1h-indazol-5-yl)-1,2-oxazole-3-carboxamide Chemical compound C1=C(C=2C=C3C=NNC3=CC=2)ON=C1C(=O)NC(C=1C=CC=CC=1)CN1C=CN=C1 GKVMBHXCXNESJY-UHFFFAOYSA-N 0.000 claims description 2
- XKVHLXGEIVAUGA-UHFFFAOYSA-N n-(3,4-dihydro-1h-isochromen-4-yl)-5-(1h-indazol-5-yl)-1,2-oxazole-3-carboxamide Chemical compound C1=C2NN=CC2=CC(C2=CC(=NO2)C(NC2C3=CC=CC=C3COC2)=O)=C1 XKVHLXGEIVAUGA-UHFFFAOYSA-N 0.000 claims description 2
- VCYLFUMELPQTPD-UHFFFAOYSA-N n-(3,4-dihydro-2h-1,5-benzodioxepin-6-ylmethyl)-5-(1h-indazol-5-yl)-1,2-oxazole-3-carboxamide Chemical compound O1CCCOC2=C1C=CC=C2CNC(=O)C1=NOC(C=2C=C3C=NNC3=CC=2)=C1 VCYLFUMELPQTPD-UHFFFAOYSA-N 0.000 claims description 2
- SENUIYRNLCTXDG-UHFFFAOYSA-N n-(4-chlorophenyl)-2-(1h-indazol-5-yl)imidazo[1,2-a]pyrimidin-3-amine Chemical compound C1=CC(Cl)=CC=C1NC1=C(C=2C=C3C=NNC3=CC=2)N=C2N1C=CC=N2 SENUIYRNLCTXDG-UHFFFAOYSA-N 0.000 claims description 2
- VRPYZMCHDCZCIA-UHFFFAOYSA-N n-(cyclohexylmethyl)-5-(1h-indazol-5-yl)-1,2-oxazole-3-carboxamide Chemical compound C1=C(C=2C=C3C=NNC3=CC=2)ON=C1C(=O)NCC1CCCCC1 VRPYZMCHDCZCIA-UHFFFAOYSA-N 0.000 claims description 2
- UKELQCQYBPBEQX-MRXNPFEDSA-N n-[(1r)-3-hydroxy-1-phenylpropyl]-5-(1h-indazol-5-yl)-1,2-oxazole-3-carboxamide Chemical compound C1([C@H](NC(=O)C2=NOC(=C2)C=2C=C3C=NNC3=CC=2)CCO)=CC=CC=C1 UKELQCQYBPBEQX-MRXNPFEDSA-N 0.000 claims description 2
- JYEMPAJMVFZOGQ-QGZVFWFLSA-N n-[(1r)-3-hydroxy-1-phenylpropyl]-5-(3-methyl-2h-indazol-5-yl)-1,2-oxazole-3-carboxamide Chemical compound C1([C@@H](CCO)NC(=O)C=2C=C(ON=2)C2=CC=C3NN=C(C3=C2)C)=CC=CC=C1 JYEMPAJMVFZOGQ-QGZVFWFLSA-N 0.000 claims description 2
- SDQFPSZDXCAAKM-JTQLQIEISA-N n-[(1s)-1-(3,4-difluorophenyl)ethyl]-5-(1h-indazol-5-yl)-1,2-oxazole-3-carboxamide Chemical compound C1([C@@H](NC(=O)C2=NOC(=C2)C=2C=C3C=NNC3=CC=2)C)=CC=C(F)C(F)=C1 SDQFPSZDXCAAKM-JTQLQIEISA-N 0.000 claims description 2
- CUVVFNKLJGANNU-NSHDSACASA-N n-[(1s)-1-(4-bromophenyl)ethyl]-5-(1h-indazol-5-yl)-1,2-oxazole-3-carboxamide Chemical compound C1([C@@H](NC(=O)C2=NOC(=C2)C=2C=C3C=NNC3=CC=2)C)=CC=C(Br)C=C1 CUVVFNKLJGANNU-NSHDSACASA-N 0.000 claims description 2
- DPBRWUCXOIUBGS-NSHDSACASA-N n-[(1s)-1-(4-chlorophenyl)ethyl]-5-(1h-indazol-5-yl)-1,2-oxazole-3-carboxamide Chemical compound C1([C@@H](NC(=O)C2=NOC(=C2)C=2C=C3C=NNC3=CC=2)C)=CC=C(Cl)C=C1 DPBRWUCXOIUBGS-NSHDSACASA-N 0.000 claims description 2
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- UKELQCQYBPBEQX-INIZCTEOSA-N n-[(1s)-3-hydroxy-1-phenylpropyl]-5-(1h-indazol-5-yl)-1,2-oxazole-3-carboxamide Chemical compound C1([C@@H](NC(=O)C2=NOC(=C2)C=2C=C3C=NNC3=CC=2)CCO)=CC=CC=C1 UKELQCQYBPBEQX-INIZCTEOSA-N 0.000 claims description 2
- HFEXDTNDWMSLIM-MJGOQNOKSA-N n-[(1s,2r)-2-hydroxy-2,3-dihydro-1h-inden-1-yl]-5-(1h-indazol-5-yl)-1,2-oxazole-3-carboxamide Chemical compound C1=C2NN=CC2=CC(C2=CC(=NO2)C(=O)N[C@H]2C3=CC=CC=C3C[C@H]2O)=C1 HFEXDTNDWMSLIM-MJGOQNOKSA-N 0.000 claims description 2
- TXDOWJLFZWXTCN-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]-5-(1h-indazol-5-yl)-1,2-oxazole-3-carboxamide Chemical compound ClC1=CC=CC=C1CNC(=O)C1=NOC(C=2C=C3C=NNC3=CC=2)=C1 TXDOWJLFZWXTCN-UHFFFAOYSA-N 0.000 claims description 2
- UYGCLUVAUDKCHM-INIZCTEOSA-N n-[(2s)-1-hydroxy-3-phenylpropan-2-yl]-5-(1h-indazol-5-yl)-1,2-oxazole-3-carboxamide Chemical compound C([C@@H](CO)NC(=O)C1=NOC(=C1)C=1C=C2C=NNC2=CC=1)C1=CC=CC=C1 UYGCLUVAUDKCHM-INIZCTEOSA-N 0.000 claims description 2
- IYUCRQKVQWEPKC-UHFFFAOYSA-N n-[(3-chlorophenyl)methyl]-5-(1h-indazol-5-yl)-1,2-oxazole-3-carboxamide Chemical compound ClC1=CC=CC(CNC(=O)C2=NOC(=C2)C=2C=C3C=NNC3=CC=2)=C1 IYUCRQKVQWEPKC-UHFFFAOYSA-N 0.000 claims description 2
- XZOCXJVSXHUNIE-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-5-(1h-indazol-5-yl)-1,2-oxazole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1CNC(=O)C1=NOC(C=2C=C3C=NNC3=CC=2)=C1 XZOCXJVSXHUNIE-UHFFFAOYSA-N 0.000 claims description 2
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- OYJIUOKIGTXNKA-UHFFFAOYSA-N n-[1-(3,5-dichlorophenyl)-2-hydroxyethyl]-5-(1h-indazol-5-yl)-1,2-oxazole-3-carboxamide Chemical compound C1=C(C=2C=C3C=NNC3=CC=2)ON=C1C(=O)NC(CO)C1=CC(Cl)=CC(Cl)=C1 OYJIUOKIGTXNKA-UHFFFAOYSA-N 0.000 claims description 2
- LSRXHUPALIXVOI-UHFFFAOYSA-N n-[1-(4-ethoxyphenyl)-2-hydroxyethyl]-5-(1h-indazol-5-yl)-1,2-oxazole-3-carboxamide Chemical compound C1=CC(OCC)=CC=C1C(CO)NC(=O)C1=NOC(C=2C=C3C=NNC3=CC=2)=C1 LSRXHUPALIXVOI-UHFFFAOYSA-N 0.000 claims description 2
- SAMOBMMKTWKJOS-UHFFFAOYSA-N n-[1-benzoyl-5-(1-benzyl-5-cyclopropyltriazol-4-yl)indazol-3-yl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(C1=CC(=CC=C11)C2=C(N(CC=3C=CC=CC=3)N=N2)C2CC2)=NN1C(=O)C1=CC=CC=C1 SAMOBMMKTWKJOS-UHFFFAOYSA-N 0.000 claims description 2
- LKCQSAXJRCNMOE-UHFFFAOYSA-N n-[2-(2-chlorophenyl)ethyl]-5-(1h-indazol-5-yl)-1,2-oxazole-3-carboxamide Chemical compound ClC1=CC=CC=C1CCNC(=O)C1=NOC(C=2C=C3C=NNC3=CC=2)=C1 LKCQSAXJRCNMOE-UHFFFAOYSA-N 0.000 claims description 2
- OYHFROGUSAVMOQ-UHFFFAOYSA-N n-[2-(3-chlorophenyl)ethyl]-5-(1h-indazol-5-yl)-1,2-oxazole-3-carboxamide Chemical compound ClC1=CC=CC(CCNC(=O)C2=NOC(=C2)C=2C=C3C=NNC3=CC=2)=C1 OYHFROGUSAVMOQ-UHFFFAOYSA-N 0.000 claims description 2
- CZQTUVAXKORGHT-UHFFFAOYSA-N n-[2-(4-chlorophenyl)ethyl]-5-(1h-indazol-5-yl)-1,2-oxazole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1CCNC(=O)C1=NOC(C=2C=C3C=NNC3=CC=2)=C1 CZQTUVAXKORGHT-UHFFFAOYSA-N 0.000 claims description 2
- RCAXGICAXATOFQ-UHFFFAOYSA-N n-[2-hydroxy-1-(2-methoxyphenyl)ethyl]-5-(1h-indazol-5-yl)-1,2-oxazole-3-carboxamide Chemical compound COC1=CC=CC=C1C(CO)NC(=O)C1=NOC(C=2C=C3C=NNC3=CC=2)=C1 RCAXGICAXATOFQ-UHFFFAOYSA-N 0.000 claims description 2
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Applications Claiming Priority (3)
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US93396007P | 2007-06-08 | 2007-06-08 | |
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PCT/US2008/065727 WO2008154241A1 (en) | 2007-06-08 | 2008-06-04 | 5-heteroaryl substituted indazoles as kinase inhibitors |
Publications (1)
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CA2689117A1 true CA2689117A1 (en) | 2008-12-18 |
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CA002689117A Abandoned CA2689117A1 (en) | 2007-06-08 | 2008-06-04 | 5-heteroaryl substituted indazoles as kinase inhibitors |
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EP (1) | EP2167491A1 (ja) |
JP (2) | JP5451602B2 (ja) |
KR (1) | KR20100032886A (ja) |
CN (1) | CN101790526A (ja) |
AU (1) | AU2008262038A1 (ja) |
BR (1) | BRPI0811065A2 (ja) |
CA (1) | CA2689117A1 (ja) |
IL (1) | IL202318A0 (ja) |
MX (1) | MX2009013213A (ja) |
RU (1) | RU2487873C2 (ja) |
SG (1) | SG182187A1 (ja) |
WO (1) | WO2008154241A1 (ja) |
ZA (1) | ZA200908624B (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11390609B2 (en) | 2017-06-30 | 2022-07-19 | Beijing Tide Pharmaceutical Co., Ltd. | Rho-associated protein kinase inhibitor, pharmaceutical composition comprising same, and preparation method and use thereof |
Families Citing this family (112)
Publication number | Priority date | Publication date | Assignee | Title |
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US8546404B2 (en) | 2005-12-13 | 2013-10-01 | Merck Sharp & Dohme | Compounds that are ERK inhibitors |
EP1984331B1 (en) | 2006-02-16 | 2010-10-20 | Schering Corporation | Pyrrolidine derivatives as erk inhibitors |
US8648069B2 (en) * | 2007-06-08 | 2014-02-11 | Abbvie Inc. | 5-substituted indazoles as kinase inhibitors |
US20110301155A1 (en) * | 2007-06-19 | 2011-12-08 | Tsuneo Yasuma | Indazole compounds for activating glucokinase |
AU2008276512A1 (en) | 2007-07-17 | 2009-01-22 | Amgen Inc. | Thiadiazole modulators of PKB |
AU2008276521B2 (en) | 2007-07-17 | 2011-11-03 | Amgen Inc. | Heterocyclic modulators of PKB |
JPWO2009028543A1 (ja) * | 2007-08-30 | 2010-12-02 | 武田薬品工業株式会社 | 置換ピラゾール誘導体 |
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US11390609B2 (en) | 2017-06-30 | 2022-07-19 | Beijing Tide Pharmaceutical Co., Ltd. | Rho-associated protein kinase inhibitor, pharmaceutical composition comprising same, and preparation method and use thereof |
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Publication number | Publication date |
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EP2167491A1 (en) | 2010-03-31 |
JP2010529137A (ja) | 2010-08-26 |
KR20100032886A (ko) | 2010-03-26 |
JP2014074057A (ja) | 2014-04-24 |
SG182187A1 (en) | 2012-07-30 |
RU2009149696A (ru) | 2011-07-20 |
RU2487873C2 (ru) | 2013-07-20 |
CN101790526A (zh) | 2010-07-28 |
MX2009013213A (es) | 2010-03-30 |
JP5451602B2 (ja) | 2014-03-26 |
WO2008154241A1 (en) | 2008-12-18 |
ZA200908624B (en) | 2015-08-26 |
AU2008262038A1 (en) | 2008-12-18 |
IL202318A0 (en) | 2010-06-30 |
BRPI0811065A2 (pt) | 2014-12-02 |
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