JP2015523387A5 - - Google Patents
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- Publication number
- JP2015523387A5 JP2015523387A5 JP2015523172A JP2015523172A JP2015523387A5 JP 2015523387 A5 JP2015523387 A5 JP 2015523387A5 JP 2015523172 A JP2015523172 A JP 2015523172A JP 2015523172 A JP2015523172 A JP 2015523172A JP 2015523387 A5 JP2015523387 A5 JP 2015523387A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazol
- ylmethyl
- phenoxy
- yloxy
- pyridin
- 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.)
- Granted
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- -1 = O Chemical group 0.000 claims 33
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 24
- 125000000623 heterocyclic group Chemical group 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000001475 halogen functional group Chemical group 0.000 claims 5
- 125000005647 linker group Chemical group 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- IFVFOBKPWWNHFY-UHFFFAOYSA-N (1-hydroxycyclopropyl)-[4-[[6-[4-(1h-pyrazol-5-yl)phenoxy]quinolin-2-yl]methyl]piperazin-1-yl]methanone Chemical compound C1CN(CC=2N=C3C=CC(OC=4C=CC(=CC=4)C=4NN=CC=4)=CC3=CC=2)CCN1C(=O)C1(O)CC1 IFVFOBKPWWNHFY-UHFFFAOYSA-N 0.000 claims 1
- ZCHQIMVQVKLHBO-GOTSBHOMSA-N (1s,2s)-2-[methyl-[[6-[4-(1h-pyrazol-5-yl)phenoxy]-1h-benzimidazol-2-yl]methyl]amino]cyclohexan-1-ol Chemical compound CN([C@@H]1[C@H](CCCC1)O)CC(NC1=CC=2)=NC1=CC=2OC(C=C1)=CC=C1C1=CC=NN1 ZCHQIMVQVKLHBO-GOTSBHOMSA-N 0.000 claims 1
- QQBNHIPXAMSXDB-OALUTQOASA-N (1s,5s)-3-[[6-[4-(1h-pyrazol-5-yl)phenoxy]-1h-benzimidazol-2-yl]methyl]-8-oxa-3-azabicyclo[3.2.1]octane Chemical compound C([C@@]1(CC[C@@](C2)(O1)[H])[H])N2CC(NC1=CC=2)=NC1=CC=2OC(C=C1)=CC=C1C1=CC=NN1 QQBNHIPXAMSXDB-OALUTQOASA-N 0.000 claims 1
- VQSPDJXKRNSSRK-SFHVURJKSA-N (2s)-2-hydroxy-1-[4-[[6-[4-(1h-pyrazol-5-yl)phenoxy]quinolin-2-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=CC=C(C=C(OC=2C=CC(=CC=2)C=2NN=CC=2)C=C2)C2=N1 VQSPDJXKRNSSRK-SFHVURJKSA-N 0.000 claims 1
- PZILIWJLCPPYMG-VWLOTQADSA-N (2s)-2-phenyl-2-[[6-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-2-yl]methylamino]acetamide Chemical compound N([C@H](C(=O)N)C=1C=CC=CC=1)CC(N=C1C=C2)=CC=C1C=C2OC(N=C1)=CC=C1C1=CC=NN1 PZILIWJLCPPYMG-VWLOTQADSA-N 0.000 claims 1
- HSTMOISBVYSKBD-INIZCTEOSA-N (2s)-n-ethyl-1-methoxy-n-[[6-[4-(1h-pyrazol-5-yl)phenoxy]-1h-benzimidazol-2-yl]methyl]propan-2-amine Chemical compound C=1C=C2NC(CN(CC)[C@@H](C)COC)=NC2=CC=1OC(C=C1)=CC=C1C1=CC=NN1 HSTMOISBVYSKBD-INIZCTEOSA-N 0.000 claims 1
- MCBRYUMNYSUPNR-IYBDPMFKSA-N (2s,6r)-2,6-dimethyl-4-[[6-[4-(1h-pyrazol-5-yl)phenoxy]-1h-benzimidazol-2-yl]methyl]morpholine Chemical compound C1[C@@H](C)O[C@@H](C)CN1CC1=NC2=CC(OC=3C=CC(=CC=3)C=3NN=CC=3)=CC=C2N1 MCBRYUMNYSUPNR-IYBDPMFKSA-N 0.000 claims 1
- CFMJYWFFWOMPKU-IRXDYDNUSA-N (2s,6s)-2,6-dimethyl-4-[[6-[[4-(1h-pyrazol-5-yl)phenyl]methyl]-1h-benzimidazol-2-yl]methyl]morpholine Chemical compound C1[C@H](C)O[C@@H](C)CN1CC(NC1=C2)=NC1=CC=C2CC1=CC=C(C=2NN=CC=2)C=C1 CFMJYWFFWOMPKU-IRXDYDNUSA-N 0.000 claims 1
- WIKGOYCAOBBNTN-INIZCTEOSA-N (3r)-1-[[6-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-2-yl]methyl]pyrrolidine-3-carbonitrile Chemical compound C1[C@H](C#N)CCN1CC1=CC=C(C=C(OC=2N=CC(=CC=2)C=2NN=CC=2)C=C2)C2=N1 WIKGOYCAOBBNTN-INIZCTEOSA-N 0.000 claims 1
- NLICEIZLJIPMOZ-MRXNPFEDSA-N (3r)-n-methyl-n-[[6-[4-(1h-pyrazol-5-yl)phenoxy]-1h-benzimidazol-2-yl]methyl]oxolan-3-amine Chemical compound CN([C@H]1COCC1)CC(NC1=CC=2)=NC1=CC=2OC(C=C1)=CC=C1C1=CC=NN1 NLICEIZLJIPMOZ-MRXNPFEDSA-N 0.000 claims 1
- DMCBYAJTPSLYRF-HNNXBMFYSA-N (3s)-1-[[6-[4-(1h-pyrazol-5-yl)phenoxy]-1h-benzimidazol-2-yl]methyl]pyrrolidin-3-ol Chemical compound C1[C@@H](O)CCN1CC(NC1=C2)=NC1=CC=C2OC1=CC=C(C=2NN=CC=2)C=C1 DMCBYAJTPSLYRF-HNNXBMFYSA-N 0.000 claims 1
- CBXSVYDQRXUHOZ-SFHVURJKSA-N (3s)-1-[[6-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-2-yl]methyl]pyrrolidin-3-ol Chemical compound C1[C@@H](O)CCN1CC1=CC=C(C=C(OC=2N=CC(=CC=2)C=2NN=CC=2)C=C2)C2=N1 CBXSVYDQRXUHOZ-SFHVURJKSA-N 0.000 claims 1
- QHOWKGIBWNFMGZ-FQEVSTJZSA-N (3s)-3-[[6-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-2-yl]methylamino]pyrrolidin-2-one Chemical compound O=C1NCC[C@@H]1NCC1=CC=C(C=C(OC=2N=CC(=CC=2)C=2NN=CC=2)C=C2)C2=N1 QHOWKGIBWNFMGZ-FQEVSTJZSA-N 0.000 claims 1
- DDNDGMWWIBXYCG-SANMLTNESA-N (3s)-3-hydroxy-1-[1-[[6-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxynaphthalen-2-yl]methyl]piperidin-4-yl]pyrrolidin-2-one Chemical compound O=C1[C@@H](O)CCN1C1CCN(CC=2C=C3C=CC(OC=4N=CC(=CC=4)C=4NN=CC=4)=CC3=CC=2)CC1 DDNDGMWWIBXYCG-SANMLTNESA-N 0.000 claims 1
- GTJLDVVTURSXGH-HNNXBMFYSA-N (3s)-3-methyl-4-[[6-[4-(1h-pyrazol-5-yl)phenoxy]-1h-benzimidazol-2-yl]methyl]morpholine Chemical compound C[C@H]1COCCN1CC1=NC2=CC(OC=3C=CC(=CC=3)C=3NN=CC=3)=CC=C2N1 GTJLDVVTURSXGH-HNNXBMFYSA-N 0.000 claims 1
- AEKZLAYERXIEPV-HNNXBMFYSA-N (3s)-n-[[6-[4-(1h-pyrazol-5-yl)phenoxy]-1h-benzimidazol-2-yl]methyl]oxolan-3-amine Chemical compound N=1C2=CC(OC=3C=CC(=CC=3)C=3NN=CC=3)=CC=C2NC=1CN[C@H]1CCOC1 AEKZLAYERXIEPV-HNNXBMFYSA-N 0.000 claims 1
- NLICEIZLJIPMOZ-INIZCTEOSA-N (3s)-n-methyl-n-[[6-[4-(1h-pyrazol-5-yl)phenoxy]-1h-benzimidazol-2-yl]methyl]oxolan-3-amine Chemical compound CN([C@@H]1COCC1)CC(NC1=CC=2)=NC1=CC=2OC(C=C1)=CC=C1C1=CC=NN1 NLICEIZLJIPMOZ-INIZCTEOSA-N 0.000 claims 1
- VHPMVZBCNHLNDN-HOTGVXAUSA-N (3s,5s)-3,5-dimethyl-4-[[6-[4-(1h-pyrazol-5-yl)phenoxy]-1h-benzimidazol-2-yl]methyl]morpholine Chemical compound C[C@H]1COC[C@H](C)N1CC1=NC2=CC(OC=3C=CC(=CC=3)C=3NN=CC=3)=CC=C2N1 VHPMVZBCNHLNDN-HOTGVXAUSA-N 0.000 claims 1
- LSTZAADQVYMEGP-GOSISDBHSA-N (5r)-5-[[6-[4-(1h-pyrazol-5-yl)phenoxy]imidazo[1,2-a]pyridin-2-yl]methoxy]piperidin-2-one Chemical compound C1NC(=O)CC[C@H]1OCC1=CN(C=C(OC=2C=CC(=CC=2)C=2NN=CC=2)C=C2)C2=N1 LSTZAADQVYMEGP-GOSISDBHSA-N 0.000 claims 1
- GICNMVGQMHRWML-IBGZPJMESA-N (5s)-5-[6-[4-(1h-pyrazol-5-yl)phenoxy]quinolin-2-yl]oxypiperidin-2-one Chemical compound C1NC(=O)CC[C@@H]1OC1=CC=C(C=C(OC=2C=CC(=CC=2)C=2NN=CC=2)C=C2)C2=N1 GICNMVGQMHRWML-IBGZPJMESA-N 0.000 claims 1
- ZPECYVOUACBRAL-INIZCTEOSA-N (5s)-5-[[5-[4-(1h-pyrazol-5-yl)phenoxy]indazol-2-yl]methyl]pyrrolidin-2-one Chemical compound N1C(=O)CC[C@H]1CN1N=C2C=CC(OC=3C=CC(=CC=3)C=3NN=CC=3)=CC2=C1 ZPECYVOUACBRAL-INIZCTEOSA-N 0.000 claims 1
- LWIVKWCGQULCQD-HNNXBMFYSA-N (5s)-5-[[5-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyindazol-1-yl]methyl]pyrrolidin-2-one Chemical compound N1C(=O)CC[C@H]1CN1C2=CC=C(OC=3N=CC(=CC=3)C=3NN=CC=3)C=C2C=N1 LWIVKWCGQULCQD-HNNXBMFYSA-N 0.000 claims 1
- GHKGGIKBGMUWIS-KRWDZBQOSA-N (5s)-5-[[6-[4-(1h-pyrazol-5-yl)phenoxy]isoquinolin-1-yl]oxymethyl]pyrrolidin-2-one Chemical compound N1C(=O)CC[C@H]1COC1=NC=CC2=CC(OC=3C=CC(=CC=3)C=3NN=CC=3)=CC=C12 GHKGGIKBGMUWIS-KRWDZBQOSA-N 0.000 claims 1
- 125000005960 1,4-diazepanyl group Chemical group 0.000 claims 1
- 125000005962 1,4-oxazepanyl group Chemical group 0.000 claims 1
- WDXWPPAHOUXELJ-UHFFFAOYSA-N 1-(1,4-dioxan-2-yl)-n-methyl-n-[[6-[4-(1h-pyrazol-5-yl)phenoxy]-1h-benzimidazol-2-yl]methyl]methanamine Chemical compound N=1C2=CC(OC=3C=CC(=CC=3)C=3NN=CC=3)=CC=C2NC=1CN(C)CC1COCCO1 WDXWPPAHOUXELJ-UHFFFAOYSA-N 0.000 claims 1
- DZAOREJXYFNBJA-UHFFFAOYSA-N 1-(oxan-4-yl)-n-[[6-[4-(1h-pyrazol-5-yl)phenoxy]-1h-benzimidazol-2-yl]methyl]methanamine Chemical compound C1COCCC1CNCC(NC1=CC=2)=NC1=CC=2OC(C=C1)=CC=C1C1=CC=NN1 DZAOREJXYFNBJA-UHFFFAOYSA-N 0.000 claims 1
- FVKPKLGUBVWBLT-UHFFFAOYSA-N 1-(oxolan-2-yl)-n-[[6-[4-(1h-pyrazol-5-yl)phenoxy]-1h-benzimidazol-2-yl]methyl]methanamine Chemical compound C1CCOC1CNCC(NC1=CC=2)=NC1=CC=2OC(C=C1)=CC=C1C1=CC=NN1 FVKPKLGUBVWBLT-UHFFFAOYSA-N 0.000 claims 1
- QPVIYPPRTZGLTH-LBAQZLPGSA-N 1-[(1s)-5-[[6-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-2-yl]methyl]-2,5-diazabicyclo[2.2.1]heptan-2-yl]ethanone Chemical compound C([C@](N(C1)C(C)=O)(C2)[H])C1N2CC(N=C1C=C2)=CC=C1C=C2OC(N=C1)=CC=C1C=1C=CNN=1 QPVIYPPRTZGLTH-LBAQZLPGSA-N 0.000 claims 1
- FVKPKLGUBVWBLT-GOSISDBHSA-N 1-[(2r)-oxolan-2-yl]-n-[[6-[4-(1h-pyrazol-5-yl)phenoxy]-1h-benzimidazol-2-yl]methyl]methanamine Chemical compound C([C@@H]1OCCC1)NCC(NC1=CC=2)=NC1=CC=2OC(C=C1)=CC=C1C1=CC=NN1 FVKPKLGUBVWBLT-GOSISDBHSA-N 0.000 claims 1
- FVKPKLGUBVWBLT-SFHVURJKSA-N 1-[(2s)-oxolan-2-yl]-n-[[6-[4-(1h-pyrazol-5-yl)phenoxy]-1h-benzimidazol-2-yl]methyl]methanamine Chemical compound C([C@H]1OCCC1)NCC(NC1=CC=2)=NC1=CC=2OC(C=C1)=CC=C1C1=CC=NN1 FVKPKLGUBVWBLT-SFHVURJKSA-N 0.000 claims 1
- YJQOQHAGGJOSAV-NRFANRHFSA-N 1-[(3s)-3-(hydroxymethyl)-4-[[6-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-2-yl]methyl]piperazin-1-yl]ethanone Chemical compound OC[C@@H]1CN(C(=O)C)CCN1CC1=CC=C(C=C(OC=2N=CC(=CC=2)C=2NN=CC=2)C=C2)C2=N1 YJQOQHAGGJOSAV-NRFANRHFSA-N 0.000 claims 1
- SDNRQYIHEQYIAQ-UHFFFAOYSA-N 1-[1-[2-[5-[4-(1h-pyrazol-5-yl)phenoxy]indazol-1-yl]ethyl]piperidin-4-yl]pyrrolidin-2-one Chemical compound O=C1CCCN1C1CCN(CCN2C3=CC=C(OC=4C=CC(=CC=4)C=4NN=CC=4)C=C3C=N2)CC1 SDNRQYIHEQYIAQ-UHFFFAOYSA-N 0.000 claims 1
- KTVJPFLVEAFOBJ-UHFFFAOYSA-N 1-[1-[[6-[4-(1h-pyrazol-5-yl)phenoxy]-2,3-dihydro-1-benzofuran-2-yl]methyl]piperidin-4-yl]pyrrolidin-2-one Chemical compound O=C1CCCN1C1CCN(CC2OC3=CC(OC=4C=CC(=CC=4)C=4NN=CC=4)=CC=C3C2)CC1 KTVJPFLVEAFOBJ-UHFFFAOYSA-N 0.000 claims 1
- IFPGAJVLPUNQML-UHFFFAOYSA-N 1-[1-[[6-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxy-2,3-dihydro-1-benzofuran-2-yl]methyl]piperidin-4-yl]pyrrolidin-2-one Chemical compound O=C1CCCN1C1CCN(CC2OC3=CC(OC=4N=CC(=CC=4)C=4NN=CC=4)=CC=C3C2)CC1 IFPGAJVLPUNQML-UHFFFAOYSA-N 0.000 claims 1
- AQVYQCGFNDJTDQ-UHFFFAOYSA-N 1-[2-[[6-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-2-yl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-5-yl]ethanone Chemical compound C1C2CN(C(=O)C)CC2CN1CC(N=C1C=C2)=CC=C1C=C2OC(N=C1)=CC=C1C1=CC=NN1 AQVYQCGFNDJTDQ-UHFFFAOYSA-N 0.000 claims 1
- FYFQGZWOBIQLKI-UHFFFAOYSA-N 1-[3-[[methyl-[[6-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-2-yl]methyl]amino]methyl]azetidin-1-yl]ethanone Chemical compound C=1C=C2C=C(OC=3N=CC(=CC=3)C=3NN=CC=3)C=CC2=NC=1CN(C)CC1CN(C(C)=O)C1 FYFQGZWOBIQLKI-UHFFFAOYSA-N 0.000 claims 1
- ZIKUPLGQIWYEJB-UHFFFAOYSA-N 1-[4-[2-[5-[4-(1h-pyrazol-5-yl)phenoxy]indazol-1-yl]ethyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CCN1C2=CC=C(OC=3C=CC(=CC=3)C=3NN=CC=3)C=C2C=N1 ZIKUPLGQIWYEJB-UHFFFAOYSA-N 0.000 claims 1
- GOQUUIMJQZQXCY-UHFFFAOYSA-N 1-[4-[2-[5-[4-(1h-pyrazol-5-yl)phenoxy]indazol-2-yl]ethyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CCN1N=C2C=CC(OC=3C=CC(=CC=3)C=3NN=CC=3)=CC2=C1 GOQUUIMJQZQXCY-UHFFFAOYSA-N 0.000 claims 1
- DODRESGUWBQESN-UHFFFAOYSA-N 1-[4-[2-[5-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyindazol-1-yl]ethyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CCN1C2=CC=C(OC=3N=CC(=CC=3)C=3NN=CC=3)C=C2C=N1 DODRESGUWBQESN-UHFFFAOYSA-N 0.000 claims 1
- HNCQIANMHNFLCL-UHFFFAOYSA-N 1-[4-[2-[5-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyindol-1-yl]ethyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CCN1C2=CC=C(OC=3N=CC(=CC=3)C=3NN=CC=3)C=C2C=C1 HNCQIANMHNFLCL-UHFFFAOYSA-N 0.000 claims 1
- RCTXHOZAIVHGFY-UHFFFAOYSA-N 1-[4-[2-[6-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxy-1-benzofuran-3-yl]ethyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CCC1=COC2=CC(OC=3N=CC(=CC=3)C=3NN=CC=3)=CC=C12 RCTXHOZAIVHGFY-UHFFFAOYSA-N 0.000 claims 1
- AKQQLRQDMZSMFD-UHFFFAOYSA-N 1-[4-[2-[6-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxy-2,3-dihydro-1-benzofuran-3-yl]ethyl]-1,4-diazepan-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCCN1CCC1C2=CC=C(OC=3N=CC(=CC=3)C=3NN=CC=3)C=C2OC1 AKQQLRQDMZSMFD-UHFFFAOYSA-N 0.000 claims 1
- RRFUTHNPFJQDMH-UHFFFAOYSA-N 1-[4-[2-[6-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxy-2,3-dihydro-1-benzofuran-3-yl]ethyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CCC1C2=CC=C(OC=3N=CC(=CC=3)C=3NN=CC=3)C=C2OC1 RRFUTHNPFJQDMH-UHFFFAOYSA-N 0.000 claims 1
- WSAAKOOUCHELIF-UHFFFAOYSA-N 1-[4-[3-[5-[4-(1h-pyrazol-5-yl)phenoxy]indazol-2-yl]propyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CCCN1N=C2C=CC(OC=3C=CC(=CC=3)C=3NN=CC=3)=CC2=C1 WSAAKOOUCHELIF-UHFFFAOYSA-N 0.000 claims 1
- DWNTUXDWDNLLIM-UHFFFAOYSA-N 1-[4-[6-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-2-yl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C1=CC=C(C=C(OC=2N=CC(=CC=2)C=2NN=CC=2)C=C2)C2=N1 DWNTUXDWDNLLIM-UHFFFAOYSA-N 0.000 claims 1
- IZCIVWZHDWJIBQ-UHFFFAOYSA-N 1-[4-[[5-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxy-1h-indol-2-yl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CC1=CC2=CC(OC=3N=CC(=CC=3)C=3NN=CC=3)=CC=C2N1 IZCIVWZHDWJIBQ-UHFFFAOYSA-N 0.000 claims 1
- GYSHNLMYPVECDD-UHFFFAOYSA-N 1-[4-[[6-[4-(1h-pyrazol-5-yl)phenoxy]quinolin-2-yl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CC1=CC=C(C=C(OC=2C=CC(=CC=2)C=2NN=CC=2)C=C2)C2=N1 GYSHNLMYPVECDD-UHFFFAOYSA-N 0.000 claims 1
- UJZIDMOAVRUZRG-UHFFFAOYSA-N 1-[4-[[6-[4-(1h-pyrazol-5-yl)phenoxy]quinolin-2-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)CC)CCN1CC1=CC=C(C=C(OC=2C=CC(=CC=2)C=2NN=CC=2)C=C2)C2=N1 UJZIDMOAVRUZRG-UHFFFAOYSA-N 0.000 claims 1
- XBBJVLRSZZVPDG-UHFFFAOYSA-N 1-[4-[[6-[4-(1h-pyrazol-5-yl)phenoxy]quinoxalin-2-yl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CC1=CN=C(C=C(OC=2C=CC(=CC=2)C=2NN=CC=2)C=C2)C2=N1 XBBJVLRSZZVPDG-UHFFFAOYSA-N 0.000 claims 1
- OCELLLYRRBLAMV-UHFFFAOYSA-N 1-[4-[[6-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxy-1-benzofuran-3-yl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CC1=COC2=CC(OC=3N=CC(=CC=3)C=3NN=CC=3)=CC=C12 OCELLLYRRBLAMV-UHFFFAOYSA-N 0.000 claims 1
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- VZOSALFYAXVAPX-UHFFFAOYSA-N n-methyl-1-(oxolan-3-yl)-n-[[6-[4-(1h-pyrazol-5-yl)phenoxy]-1h-benzimidazol-2-yl]methyl]methanamine Chemical compound N=1C2=CC(OC=3C=CC(=CC=3)C=3NN=CC=3)=CC=C2NC=1CN(C)CC1CCOC1 VZOSALFYAXVAPX-UHFFFAOYSA-N 0.000 claims 1
- NQEDXMFIEOOFND-LJQANCHMSA-N n-methyl-1-[(2r)-oxolan-2-yl]-n-[[6-[4-(1h-pyrazol-5-yl)phenoxy]-1h-benzimidazol-2-yl]methyl]methanamine Chemical class N=1C2=CC(OC=3C=CC(=CC=3)C=3NN=CC=3)=CC=C2NC=1CN(C)C[C@H]1CCCO1 NQEDXMFIEOOFND-LJQANCHMSA-N 0.000 claims 1
- NQEDXMFIEOOFND-IBGZPJMESA-N n-methyl-1-[(2s)-oxolan-2-yl]-n-[[6-[4-(1h-pyrazol-5-yl)phenoxy]-1h-benzimidazol-2-yl]methyl]methanamine Chemical class N=1C2=CC(OC=3C=CC(=CC=3)C=3NN=CC=3)=CC=C2NC=1CN(C)C[C@@H]1CCCO1 NQEDXMFIEOOFND-IBGZPJMESA-N 0.000 claims 1
- JBXGMBUMJFGUEK-UHFFFAOYSA-N n-methyl-1-[2-[6-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxy-1-benzofuran-3-yl]ethyl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)NC)CCN1CCC1=COC2=CC(OC=3N=CC(=CC=3)C=3NN=CC=3)=CC=C12 JBXGMBUMJFGUEK-UHFFFAOYSA-N 0.000 claims 1
- GMHGSKAFBBCBPG-UHFFFAOYSA-N n-methyl-1-[6-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-2-yl]methanamine Chemical compound C1=CC2=NC(CNC)=CC=C2C=C1OC(N=C1)=CC=C1C1=CC=NN1 GMHGSKAFBBCBPG-UHFFFAOYSA-N 0.000 claims 1
- CVSQXIMBBJFSPS-UHFFFAOYSA-N n-methyl-1-[[6-[4-(1h-pyrazol-5-yl)phenoxy]-2,3-dihydro-1-benzofuran-2-yl]methyl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)NC)CCN1CC1OC2=CC(OC=3C=CC(=CC=3)C=3NN=CC=3)=CC=C2C1 CVSQXIMBBJFSPS-UHFFFAOYSA-N 0.000 claims 1
- SEOXJTRNMQSPFQ-UHFFFAOYSA-N n-methyl-n-[1-[[6-[5-(1h-pyrazol-5-yl)pyridin-2-yl]oxyquinolin-2-yl]methyl]piperidin-4-yl]acetamide Chemical compound C1CC(N(C)C(C)=O)CCN1CC1=CC=C(C=C(OC=2N=CC(=CC=2)C=2NN=CC=2)C=C2)C2=N1 SEOXJTRNMQSPFQ-UHFFFAOYSA-N 0.000 claims 1
- CRJOFMIHOFVOGJ-UHFFFAOYSA-N n-methyl-n-[[6-[4-(1h-pyrazol-5-yl)phenoxy]-1h-benzimidazol-2-yl]methyl]cyclopentanamine Chemical compound C1CCCC1N(C)CC(NC1=CC=2)=NC1=CC=2OC(C=C1)=CC=C1C1=CC=NN1 CRJOFMIHOFVOGJ-UHFFFAOYSA-N 0.000 claims 1
- LZIHOFZRBZYAMN-UHFFFAOYSA-N n-methyl-n-[[6-[4-(1h-pyrazol-5-yl)phenoxy]-1h-benzimidazol-2-yl]methyl]cyclopropanamine Chemical compound C1CC1N(C)CC(NC1=CC=2)=NC1=CC=2OC(C=C1)=CC=C1C1=CC=NN1 LZIHOFZRBZYAMN-UHFFFAOYSA-N 0.000 claims 1
- CFJNOQHDULUVAH-UHFFFAOYSA-N n-methyl-n-[[6-[4-(1h-pyrazol-5-yl)phenoxy]-1h-benzimidazol-2-yl]methyl]oxan-4-amine Chemical compound C1COCCC1N(C)CC(NC1=CC=2)=NC1=CC=2OC(C=C1)=CC=C1C1=CC=NN1 CFJNOQHDULUVAH-UHFFFAOYSA-N 0.000 claims 1
- 125000000160 oxazolidinyl group Chemical group 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 229940080818 propionamide Drugs 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
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| EP2822942B1 (en) | 2012-03-06 | 2017-05-10 | Boehringer Ingelheim International GmbH | Benzodioxanes for inhibiting leukotriene production |
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| EP2885285B1 (en) | 2012-07-17 | 2016-10-19 | Boehringer Ingelheim International GmbH | Pyrazole drivatives which inhibit leukotriene production |
| US9573957B2 (en) | 2013-07-15 | 2017-02-21 | Boehringer Ingelheim International Gmbh | Inhibitors of leukotriene production |
| JP6353899B2 (ja) * | 2013-07-15 | 2018-07-04 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ロイコトリエン生成の阻害剤 |
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| EP2822942B1 (en) | 2012-03-06 | 2017-05-10 | Boehringer Ingelheim International GmbH | Benzodioxanes for inhibiting leukotriene production |
| JP6080226B2 (ja) | 2012-03-06 | 2017-02-15 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 他の活性物質と組み合わせたロイコトリエン産生阻害用ベンゾジオキサン |
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-
2013
- 2013-07-16 EP EP13740484.4A patent/EP2885285B1/en active Active
- 2013-07-16 TW TW102125428A patent/TW201416354A/zh unknown
- 2013-07-16 AR ARP130102537 patent/AR091786A1/es unknown
- 2013-07-16 US US13/942,988 patent/US9403830B2/en active Active
- 2013-07-16 JP JP2015523172A patent/JP6256467B2/ja active Active
- 2013-07-16 WO PCT/US2013/050624 patent/WO2014014874A1/en not_active Ceased
- 2013-07-17 UY UY0001034917A patent/UY34917A/es unknown
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