JP2015509543A5 - - Google Patents
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- Publication number
- JP2015509543A5 JP2015509543A5 JP2014561149A JP2014561149A JP2015509543A5 JP 2015509543 A5 JP2015509543 A5 JP 2015509543A5 JP 2014561149 A JP2014561149 A JP 2014561149A JP 2014561149 A JP2014561149 A JP 2014561149A JP 2015509543 A5 JP2015509543 A5 JP 2015509543A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- amino
- carbonyl
- isoquinoline
- cyano
- 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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- 150000001875 compounds Chemical class 0.000 claims description 51
- 125000003118 aryl group Chemical group 0.000 claims description 47
- -1 amino, substituted amino Chemical group 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 125000001475 halogen functional group Chemical group 0.000 claims description 23
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- 102100037248 Prolyl hydroxylase EGLN2 Human genes 0.000 claims description 15
- 101710170760 Prolyl hydroxylase EGLN2 Proteins 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 13
- 102100037249 Egl nine homolog 1 Human genes 0.000 claims description 11
- 101710111663 Egl nine homolog 1 Proteins 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 102000004190 Enzymes Human genes 0.000 claims description 9
- 108090000790 Enzymes Proteins 0.000 claims description 9
- 125000004442 acylamino group Chemical group 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 239000000651 prodrug Substances 0.000 claims description 9
- 229940002612 prodrug Drugs 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 150000003857 carboxamides Chemical group 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000005110 aryl thio group Chemical group 0.000 claims description 6
- 102100037247 Prolyl hydroxylase EGLN3 Human genes 0.000 claims description 5
- 101710170720 Prolyl hydroxylase EGLN3 Proteins 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 4
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 claims description 4
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- PNTSTXDGTUPCTD-GOSISDBHSA-N (2r)-2-acetamido-4-[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]butanoic acid Chemical compound C1=CC2=C(O)C(C(=O)NCC[C@@H](NC(=O)C)C(O)=O)=NC(C#N)=C2C=C1OC1=CC=CC=C1 PNTSTXDGTUPCTD-GOSISDBHSA-N 0.000 claims description 2
- UBEYTGBZRYCLOZ-GFCCVEGCSA-N (2r)-3-[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]-2-methylpropanoic acid Chemical compound C1=CC2=C(O)C(C(=O)NC[C@@H](C)C(O)=O)=NC(C#N)=C2C=C1OC1=CC=CC=C1 UBEYTGBZRYCLOZ-GFCCVEGCSA-N 0.000 claims description 2
- TTYWGSQNECYLRX-CHWSQXEVSA-N (2r,3r)-3-[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]-2-methylbutanoic acid Chemical compound C1=CC2=C(O)C(C(=O)N[C@H](C)[C@@H](C)C(O)=O)=NC(C#N)=C2C=C1OC1=CC=CC=C1 TTYWGSQNECYLRX-CHWSQXEVSA-N 0.000 claims description 2
- TTYWGSQNECYLRX-OLZOCXBDSA-N (2r,3s)-3-[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]-2-methylbutanoic acid Chemical compound C1=CC2=C(O)C(C(=O)N[C@@H](C)[C@@H](C)C(O)=O)=NC(C#N)=C2C=C1OC1=CC=CC=C1 TTYWGSQNECYLRX-OLZOCXBDSA-N 0.000 claims description 2
- NNUUDWBQBNSVGR-HNNXBMFYSA-N (2s)-2-amino-3-[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]propanoic acid Chemical compound C1=CC2=C(O)C(C(=O)NC[C@H](N)C(O)=O)=NC(C#N)=C2C=C1OC1=CC=CC=C1 NNUUDWBQBNSVGR-HNNXBMFYSA-N 0.000 claims description 2
- LKKMGZPSABYQKE-HNNXBMFYSA-N (2s)-2-amino-3-[(4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]propanoic acid Chemical compound C1=CC2=C(O)C(C(=O)NC[C@H](N)C(O)=O)=NC=C2C=C1OC1=CC=CC=C1 LKKMGZPSABYQKE-HNNXBMFYSA-N 0.000 claims description 2
- GUSZHYVWIFSYBU-SFHVURJKSA-N (2s)-2-benzyl-3-[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]propanoic acid Chemical compound C([C@@H](C(=O)O)CC=1C=CC=CC=1)NC(=O)C(C(=C1C=C2)O)=NC(C#N)=C1C=C2OC1=CC=CC=C1 GUSZHYVWIFSYBU-SFHVURJKSA-N 0.000 claims description 2
- GXDHDFVYIIBWGX-HNNXBMFYSA-N (2s)-2-hydroxy-3-[(4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]propanoic acid Chemical compound C1=CC2=C(O)C(C(=O)NC[C@H](O)C(O)=O)=NC=C2C=C1OC1=CC=CC=C1 GXDHDFVYIIBWGX-HNNXBMFYSA-N 0.000 claims description 2
- HBPBZJAYBQVBDY-INIZCTEOSA-N (2s)-2-hydroxy-3-[[4-hydroxy-7-(4-methoxyphenoxy)isoquinoline-3-carbonyl]amino]propanoic acid Chemical compound C1=CC(OC)=CC=C1OC1=CC=C(C(O)=C(N=C2)C(=O)NC[C@H](O)C(O)=O)C2=C1 HBPBZJAYBQVBDY-INIZCTEOSA-N 0.000 claims description 2
- XNRNJKKKWOCNLH-HNNXBMFYSA-N (2s)-2-hydroxy-3-[[4-hydroxy-7-(phenylcarbamoylamino)isoquinoline-3-carbonyl]amino]propanoic acid Chemical compound C1=CC2=C(O)C(C(=O)NC[C@H](O)C(O)=O)=NC=C2C=C1NC(=O)NC1=CC=CC=C1 XNRNJKKKWOCNLH-HNNXBMFYSA-N 0.000 claims description 2
- IGBKLAZQWUSTAU-INIZCTEOSA-N (2s)-2-hydroxy-4-[(4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]butanoic acid Chemical compound C1=CC2=C(O)C(C(=O)NCC[C@H](O)C(O)=O)=NC=C2C=C1OC1=CC=CC=C1 IGBKLAZQWUSTAU-INIZCTEOSA-N 0.000 claims description 2
- GAXREOLLPRQLNE-QHCPKHFHSA-N (2s)-3-[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]-2-(phenylmethoxycarbonylamino)propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)OCC=1C=CC=CC=1)NC(=O)C(C(=C1C=C2)O)=NC(C#N)=C1C=C2OC1=CC=CC=C1 GAXREOLLPRQLNE-QHCPKHFHSA-N 0.000 claims description 2
- UOUOUOFRJQINNR-IBGZPJMESA-N (2s)-3-[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound C1=CC2=C(O)C(C(=O)NC[C@H](NC(=O)OC(C)(C)C)C(O)=O)=NC(C#N)=C2C=C1OC1=CC=CC=C1 UOUOUOFRJQINNR-IBGZPJMESA-N 0.000 claims description 2
- OTQFWKODLCHMMB-INIZCTEOSA-N (2s)-3-[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]-2-hydroxypropanoic acid Chemical compound C1=CC2=C(O)C(C(=O)NC[C@H](O)C(O)=O)=NC(C#N)=C2C=C1OC1=CC=CC=C1 OTQFWKODLCHMMB-INIZCTEOSA-N 0.000 claims description 2
- UBEYTGBZRYCLOZ-LBPRGKRZSA-N (2s)-3-[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]-2-methylpropanoic acid Chemical compound C1=CC2=C(O)C(C(=O)NC[C@H](C)C(O)=O)=NC(C#N)=C2C=C1OC1=CC=CC=C1 UBEYTGBZRYCLOZ-LBPRGKRZSA-N 0.000 claims description 2
- POGJKBIAZPPFAR-KRWDZBQOSA-N (2s)-4-[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]-2-hydroxybutanoic acid Chemical compound C1=CC2=C(O)C(C(=O)NCC[C@H](O)C(O)=O)=NC(C#N)=C2C=C1OC1=CC=CC=C1 POGJKBIAZPPFAR-KRWDZBQOSA-N 0.000 claims description 2
- KFQULEWLVTWOGD-SFHVURJKSA-N (2s)-4-[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]-2-methoxybutanoic acid Chemical compound C1=CC2=C(O)C(C(=O)NCC[C@H](OC)C(O)=O)=NC(C#N)=C2C=C1OC1=CC=CC=C1 KFQULEWLVTWOGD-SFHVURJKSA-N 0.000 claims description 2
- TTYWGSQNECYLRX-QWHCGFSZSA-N (2s,3r)-3-[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]-2-methylbutanoic acid Chemical compound C1=CC2=C(O)C(C(=O)N[C@H](C)[C@H](C)C(O)=O)=NC(C#N)=C2C=C1OC1=CC=CC=C1 TTYWGSQNECYLRX-QWHCGFSZSA-N 0.000 claims description 2
- DGJDZGFFYSIJTN-OAQYLSRUSA-N (3r)-3-[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]-3-phenylpropanoic acid Chemical compound N([C@H](CC(=O)O)C=1C=CC=CC=1)C(=O)C(C(=C1C=C2)O)=NC(C#N)=C1C=C2OC1=CC=CC=C1 DGJDZGFFYSIJTN-OAQYLSRUSA-N 0.000 claims description 2
- BXQLMPYZVJTCLU-HXUWFJFHSA-N (3r)-3-[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]-3-pyridin-3-ylpropanoic acid Chemical compound N([C@H](CC(=O)O)C=1C=NC=CC=1)C(=O)C(C(=C1C=C2)O)=NC(C#N)=C1C=C2OC1=CC=CC=C1 BXQLMPYZVJTCLU-HXUWFJFHSA-N 0.000 claims description 2
- LRKHSAOMPJQUKY-GOSISDBHSA-N (3r)-3-[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]-4-phenylbutanoic acid Chemical compound C([C@H](CC(=O)O)NC(=O)C=1C(=C2C=CC(OC=3C=CC=CC=3)=CC2=C(C#N)N=1)O)C1=CC=CC=C1 LRKHSAOMPJQUKY-GOSISDBHSA-N 0.000 claims description 2
- WZJDYOWVFHSRTF-LJQANCHMSA-N (3r)-3-[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]-5-phenylpentanoic acid Chemical compound C([C@H](CC(=O)O)NC(=O)C=1C(=C2C=CC(OC=3C=CC=CC=3)=CC2=C(C#N)N=1)O)CC1=CC=CC=C1 WZJDYOWVFHSRTF-LJQANCHMSA-N 0.000 claims description 2
- CTADYWAQKGRMMW-GFCCVEGCSA-N (3r)-3-[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]butanoic acid Chemical compound C1=CC2=C(O)C(C(=O)N[C@@H](CC(O)=O)C)=NC(C#N)=C2C=C1OC1=CC=CC=C1 CTADYWAQKGRMMW-GFCCVEGCSA-N 0.000 claims description 2
- XBMFFUGFOFOFEO-CYBMUJFWSA-N (3r)-3-[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]pentanoic acid Chemical compound C1=CC2=C(O)C(C(=O)N[C@@H](CC(O)=O)CC)=NC(C#N)=C2C=C1OC1=CC=CC=C1 XBMFFUGFOFOFEO-CYBMUJFWSA-N 0.000 claims description 2
- LSGSPXIRMZTZQG-NRFANRHFSA-N (3s)-3-[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]-3-(2-fluorophenyl)propanoic acid Chemical compound N([C@@H](CC(=O)O)C=1C(=CC=CC=1)F)C(=O)C(C(=C1C=C2)O)=NC(C#N)=C1C=C2OC1=CC=CC=C1 LSGSPXIRMZTZQG-NRFANRHFSA-N 0.000 claims description 2
- GIOAJCVNRUNIID-QFIPXVFZSA-N (3s)-3-[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]-3-(2-methylphenyl)propanoic acid Chemical compound CC1=CC=CC=C1[C@H](CC(O)=O)NC(=O)C1=NC(C#N)=C(C=C(OC=2C=CC=CC=2)C=C2)C2=C1O GIOAJCVNRUNIID-QFIPXVFZSA-N 0.000 claims description 2
- PBGXTOQPTZOOLG-QFIPXVFZSA-N (3s)-3-[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]-3-(4-cyanophenyl)propanoic acid Chemical compound N([C@@H](CC(=O)O)C=1C=CC(=CC=1)C#N)C(=O)C(C(=C1C=C2)O)=NC(C#N)=C1C=C2OC1=CC=CC=C1 PBGXTOQPTZOOLG-QFIPXVFZSA-N 0.000 claims description 2
- DGJDZGFFYSIJTN-NRFANRHFSA-N (3s)-3-[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]-3-phenylpropanoic acid Chemical compound N([C@@H](CC(=O)O)C=1C=CC=CC=1)C(=O)C(C(=C1C=C2)O)=NC(C#N)=C1C=C2OC1=CC=CC=C1 DGJDZGFFYSIJTN-NRFANRHFSA-N 0.000 claims description 2
- BXQLMPYZVJTCLU-FQEVSTJZSA-N (3s)-3-[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]-3-pyridin-3-ylpropanoic acid Chemical compound N([C@@H](CC(=O)O)C=1C=NC=CC=1)C(=O)C(C(=C1C=C2)O)=NC(C#N)=C1C=C2OC1=CC=CC=C1 BXQLMPYZVJTCLU-FQEVSTJZSA-N 0.000 claims description 2
- LRKHSAOMPJQUKY-SFHVURJKSA-N (3s)-3-[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]-4-phenylbutanoic acid Chemical compound C([C@@H](CC(=O)O)NC(=O)C=1C(=C2C=CC(OC=3C=CC=CC=3)=CC2=C(C#N)N=1)O)C1=CC=CC=C1 LRKHSAOMPJQUKY-SFHVURJKSA-N 0.000 claims description 2
- CTADYWAQKGRMMW-LBPRGKRZSA-N (3s)-3-[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]butanoic acid Chemical compound C1=CC2=C(O)C(C(=O)N[C@H](CC(O)=O)C)=NC(C#N)=C2C=C1OC1=CC=CC=C1 CTADYWAQKGRMMW-LBPRGKRZSA-N 0.000 claims description 2
- WHDBRPBRHPLOCJ-UHFFFAOYSA-N 1-[[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]methyl]cyclobutane-1-carboxylic acid Chemical compound N=1C(C#N)=C2C=C(OC=3C=CC=CC=3)C=CC2=C(O)C=1C(=O)NCC1(C(=O)O)CCC1 WHDBRPBRHPLOCJ-UHFFFAOYSA-N 0.000 claims description 2
- JSYWJICQZNCWHF-UHFFFAOYSA-N 1-[[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]methyl]cyclopentane-1-carboxylic acid Chemical compound N=1C(C#N)=C2C=C(OC=3C=CC=CC=3)C=CC2=C(O)C=1C(=O)NCC1(C(=O)O)CCCC1 JSYWJICQZNCWHF-UHFFFAOYSA-N 0.000 claims description 2
- PDBNVENXRSQVKB-UHFFFAOYSA-N 1-[[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]methyl]cyclopropane-1-carboxylic acid Chemical compound N=1C(C#N)=C2C=C(OC=3C=CC=CC=3)C=CC2=C(O)C=1C(=O)NCC1(C(=O)O)CC1 PDBNVENXRSQVKB-UHFFFAOYSA-N 0.000 claims description 2
- WZEVEULDNFXEFI-UHFFFAOYSA-N 1-[[(1-cyano-4-hydroxy-7-phenylsulfanylisoquinoline-3-carbonyl)amino]methyl]cyclobutane-1-carboxylic acid Chemical compound N=1C(C#N)=C2C=C(SC=3C=CC=CC=3)C=CC2=C(O)C=1C(=O)NCC1(C(=O)O)CCC1 WZEVEULDNFXEFI-UHFFFAOYSA-N 0.000 claims description 2
- NYIXYQZNDODKLM-UHFFFAOYSA-N 1-[[(1-cyano-4-hydroxy-7-pyridin-3-yloxyisoquinoline-3-carbonyl)amino]methyl]cyclobutane-1-carboxylic acid Chemical compound N=1C(C#N)=C2C=C(OC=3C=NC=CC=3)C=CC2=C(O)C=1C(=O)NCC1(C(=O)O)CCC1 NYIXYQZNDODKLM-UHFFFAOYSA-N 0.000 claims description 2
- IVNASAIOJNMRBM-UHFFFAOYSA-N 1-[[(1-cyano-7-cyclohexyloxy-4-hydroxyisoquinoline-3-carbonyl)amino]methyl]cyclobutane-1-carboxylic acid Chemical compound N=1C(C#N)=C2C=C(OC3CCCCC3)C=CC2=C(O)C=1C(=O)NCC1(C(=O)O)CCC1 IVNASAIOJNMRBM-UHFFFAOYSA-N 0.000 claims description 2
- RBUHJNXKWHHZST-UHFFFAOYSA-N 1-[[(1-cyano-7-cyclohexylsulfonyl-4-hydroxyisoquinoline-3-carbonyl)amino]methyl]cyclobutane-1-carboxylic acid Chemical compound N=1C(C#N)=C2C=C(S(=O)(=O)C3CCCCC3)C=CC2=C(O)C=1C(=O)NCC1(C(=O)O)CCC1 RBUHJNXKWHHZST-UHFFFAOYSA-N 0.000 claims description 2
- FIVYBSPPKFZCNQ-UHFFFAOYSA-N 1-[[(4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]methyl]cyclobutane-1-carboxylic acid Chemical compound N=1C=C2C=C(OC=3C=CC=CC=3)C=CC2=C(O)C=1C(=O)NCC1(C(=O)O)CCC1 FIVYBSPPKFZCNQ-UHFFFAOYSA-N 0.000 claims description 2
- UFVTYNUQLCVARJ-UHFFFAOYSA-N 1-[[[1-cyano-7-(2,6-difluorophenoxy)-4-hydroxyisoquinoline-3-carbonyl]amino]methyl]cyclobutane-1-carboxylic acid Chemical compound N=1C(C#N)=C2C=C(OC=3C(=CC=CC=3F)F)C=CC2=C(O)C=1C(=O)NCC1(C(=O)O)CCC1 UFVTYNUQLCVARJ-UHFFFAOYSA-N 0.000 claims description 2
- SLBHGGUKXNMPNZ-UHFFFAOYSA-N 2-[1-[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]cyclohexyl]acetic acid Chemical compound N=1C(C#N)=C2C=C(OC=3C=CC=CC=3)C=CC2=C(O)C=1C(=O)NC1(CC(=O)O)CCCCC1 SLBHGGUKXNMPNZ-UHFFFAOYSA-N 0.000 claims description 2
- IOROJGTUVPLIBU-UHFFFAOYSA-N 2-[1-[[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]methyl]cyclohexyl]acetic acid Chemical compound N=1C(C#N)=C2C=C(OC=3C=CC=CC=3)C=CC2=C(O)C=1C(=O)NCC1(CC(=O)O)CCCCC1 IOROJGTUVPLIBU-UHFFFAOYSA-N 0.000 claims description 2
- XTXDQXMSFMWGFF-UHFFFAOYSA-N 2-[4-[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]-1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]acetic acid Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1(CC(O)=O)NC(=O)C1=NC(C#N)=C(C=C(OC=2C=CC=CC=2)C=C2)C2=C1O XTXDQXMSFMWGFF-UHFFFAOYSA-N 0.000 claims description 2
- NXMYGAXOCIIGFJ-UHFFFAOYSA-N 2-[[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]methyl]-2-methylbutanoic acid Chemical compound C1=CC2=C(O)C(C(=O)NCC(C)(CC)C(O)=O)=NC(C#N)=C2C=C1OC1=CC=CC=C1 NXMYGAXOCIIGFJ-UHFFFAOYSA-N 0.000 claims description 2
- PDDZFEWPTAIYGL-UHFFFAOYSA-N 2-[[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]methyl]-2-propylpentanoic acid Chemical compound C1=CC2=C(O)C(C(=O)NCC(CCC)(CCC)C(O)=O)=NC(C#N)=C2C=C1OC1=CC=CC=C1 PDDZFEWPTAIYGL-UHFFFAOYSA-N 0.000 claims description 2
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| NZ592741A (en) | 2008-11-14 | 2013-03-28 | Fibrogen Inc | Thiochromene derivatives as hif hydroxylase inhibitors |
| PL2872488T3 (pl) | 2012-07-16 | 2019-01-31 | Fibrogen, Inc. | Postacie krystaliczne inhibitora hydroksylazy prolilowej |
| US8883823B2 (en) | 2012-07-16 | 2014-11-11 | Fibrogen, Inc. | Crystalline forms of a prolyl hydroxylase inhibitor |
| CN103435546B (zh) | 2012-07-16 | 2016-08-10 | 菲布罗根有限公司 | 制备异喹啉化合物的方法 |
| IL296484B2 (en) | 2013-06-06 | 2025-03-01 | Fibrogen Inc | Pharmaceutical formulations of HIF hydroxylase inhibitor |
| WO2015054579A1 (en) * | 2013-10-11 | 2015-04-16 | Isis Pharmaceuticals, Inc. | Treatment of acute kidney injury with phd1 modulators |
| EP3190104B1 (en) | 2014-09-02 | 2021-10-27 | Sunshine Lake Pharma Co., Ltd. | Quinolinone compound and use thereof |
| CN106146395B (zh) | 2015-03-27 | 2019-01-01 | 沈阳三生制药有限责任公司 | 3-羟基吡啶化合物、其制备方法及其制药用途 |
| CN106146490B (zh) * | 2015-03-27 | 2018-10-23 | 沈阳三生制药有限责任公司 | 被芳氧基或杂芳氧基取代的5-羟基-1,7-萘啶化合物、其制备方法及其制药用途 |
| CN105367435A (zh) * | 2015-12-03 | 2016-03-02 | 张伟 | 一种β-丙氨酸叔丁酯盐酸盐的制备方法 |
| CN107188875B (zh) * | 2016-03-15 | 2020-11-10 | 联化科技股份有限公司 | 一种取代苯酞类化合物的制备方法及其中间体 |
| CN106478503A (zh) * | 2016-09-29 | 2017-03-08 | 上海勋和医药科技有限公司 | Roxadustat中间体的制备方法 |
| JP2019529522A (ja) | 2016-10-10 | 2019-10-17 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | ＲＯＲγ調節因子としての三環式スルホン類 |
| CN107954931B (zh) * | 2016-10-17 | 2021-06-22 | 上海医药集团青岛国风药业股份有限公司 | 一种诺得司他的制备方法 |
| WO2018140186A1 (en) | 2017-01-28 | 2018-08-02 | Kingchem Life Science Llc | A process for preparing 5-phenoxy-1(3h)isobenzofuranone |
| TW201920108A (zh) * | 2017-09-25 | 2019-06-01 | 日商武田藥品工業有限公司 | N-(氰基取代之苄基或吡啶基甲基)-3-羥基吡啶醯胺衍生物 |
| CN108084090B (zh) * | 2017-12-20 | 2020-03-17 | 北京六合宁远科技有限公司 | 一种药物中间体含氮杂环的溴代化合物的合成方法 |
| WO2021073623A1 (zh) * | 2019-10-18 | 2021-04-22 | 上海迪赛诺化学制药有限公司 | 一种制备异喹啉酮类化合物的方法 |
| CN112679430B (zh) * | 2019-10-18 | 2023-05-05 | 上海迪赛诺化学制药有限公司 | 一种制备异喹啉酮类化合物的方法 |
| CN112679431B (zh) * | 2019-10-18 | 2023-05-05 | 上海迪赛诺化学制药有限公司 | 一种制备异喹啉酮类化合物的方法 |
| CN113754569B (zh) * | 2020-06-04 | 2024-07-02 | 四川国为制药有限公司 | 一种中间体化合物及其制备方法和用途 |
| AU2022378858A1 (en) * | 2021-10-28 | 2024-05-02 | Insilico Medicine Ip Limited | Prolyl hydroxylase domain-containing protein (phd) inhibitors and uses thereof |
| WO2023111990A1 (en) * | 2021-12-17 | 2023-06-22 | Akebia Therapeutics, Inc. | Selective phd1 inhibitor compounds, compositions, and methods of use |
| EP4448493A1 (en) * | 2021-12-17 | 2024-10-23 | Akebia Therapeutics, Inc. | Picolinamide compounds as selective phd1 inhibitors, compositions, and methods of use |
| EP4463160A1 (en) * | 2022-01-13 | 2024-11-20 | Fibrogen, Inc. | Treatment for congestive heart failure |
| WO2024138317A1 (zh) * | 2022-12-26 | 2024-07-04 | 中国科学院广州生物医药与健康研究院 | 一种甲状腺激素受体β激动剂化合物及其制备方法和应用 |
| WO2024222893A1 (en) * | 2023-04-28 | 2024-10-31 | Insilico Medicine Ip Limited | Crystalline prolyl hydroxylase domain-containing protein (phd) inhibitor and uses thereof |
| CN121127469A (zh) * | 2023-04-28 | 2025-12-12 | 英矽智能科技知识产权有限公司 | 含脯氨酰羟化酶结构域的蛋白质(phd)抑制剂结晶及其用途 |
| AU2024261389A1 (en) * | 2023-04-28 | 2025-10-30 | Insilico Medicine Ip Limited | Prolyl hydroxylase domain-containing protein (phd) inhibitors, combinations and uses thereof |
| CN117486797A (zh) * | 2023-11-23 | 2024-02-02 | 传健生物医药(厦门)有限公司 | 一种罗沙司他关键中间体及罗沙司他的制备方法 |
| WO2025252553A1 (en) | 2024-06-04 | 2025-12-11 | Syngenta Crop Protection Ag | Pesticidally-active 2,2-dihalocyclopropyl compounds |
Family Cites Families (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4036964A (en) | 1973-10-11 | 1977-07-19 | Beecham Group Limited | Isocarbostyril-3-carboxylic acid derivatives for the prophylaxis of asthma, hayfever and rhinitis |
| US3989704A (en) | 1973-10-30 | 1976-11-02 | Sandoz, Inc. | 3-Substituted-4-aryl isoquinolines |
| DE2818423A1 (de) | 1978-04-27 | 1979-11-08 | Hoechst Ag | Neue isochinolinderivate und verfahren zu ihrer herstellung |
| DE3233424A1 (de) | 1982-09-09 | 1984-03-15 | Hoechst Ag, 6230 Frankfurt | Isochinolinderivate, verfahren zu ihrer herstellung, pharmazeutische praeparate auf basis dieser verbindungen und ihre verwendung |
| US4559403A (en) | 1983-05-19 | 1985-12-17 | Hoffmann-La Roche Inc. | Substituted isoquinolines |
| US4584379A (en) | 1985-01-22 | 1986-04-22 | Merrell Dow Pharmaceuticals Inc. | Isoquinoline thromboxane synthetase inhibitors |
| US4822800A (en) | 1986-06-09 | 1989-04-18 | Ortho Pharmaceutical Corporation | Isoquinolinol compounds having cardiotonic and phosphodiesterase fraction III inhibiting properties and/or renal vasodilating properties |
| US4966906A (en) | 1987-11-27 | 1990-10-30 | Hoechst-Roussel Pharmaceuticals Inc. | 1-aryl-3-isoquinolinecarboxamides |
| US4952588A (en) | 1987-11-27 | 1990-08-28 | Hoechst-Roussel Pharmaceuticals Inc. | 1-aryl-3-quinoline-and 1-aryl-3-isoquinoline-carboxamides |
| DE59401923D1 (de) | 1993-11-02 | 1997-04-10 | Hoechst Ag | Substituierte heterocyclische Carbonsäureamidester, ihre Herstellung und ihre Verwendung als Arzneimittel |
| DE59401924D1 (de) | 1993-11-02 | 1997-04-10 | Hoechst Ag | Substituierte heterocyclische Carbonsäureamide, ihre Herstellung und ihre Verwendung als Arzneimittel |
| NZ270267A (en) | 1993-12-30 | 1997-03-24 | Hoechst Ag | 3-hydroxypyridin-2yl (and -quinolin-2-yl) carboxamide derivatives and pharmaceutical compositions |
| WO1996018616A1 (en) | 1994-12-12 | 1996-06-20 | Merck & Co., Inc. | Substituted 2-aminopyridines as inhibitors of nitric oxide synthase |
| IL135495A (en) | 1995-09-28 | 2002-12-01 | Hoechst Ag | Intermediate compounds for the preparation of quinoline-converted amines - 2 - carboxylic acid |
| ATE342262T1 (de) | 1996-11-27 | 2006-11-15 | Bristol Myers Squibb Pharma Co | Neue integrin rezeptor antagonisten |
| DE19746287A1 (de) | 1997-10-20 | 1999-04-22 | Hoechst Marion Roussel De Gmbh | Substituierte Isochinolin-2-Carbonsäureamide, ihre Herstellung und ihre Verwendung als Arzneimittel |
| FR2779963A1 (fr) | 1998-06-22 | 1999-12-24 | Centre Nat Rech Scient | Utilisation d'un compose possedant une affinite pour le recepteur mitochondrial des benzodiazepines en therapie du cancer |
| IT1302677B1 (it) | 1998-10-15 | 2000-09-29 | Zambon Spa | Derivati benzazinici inibitori della fosfodiesterasi 4 |
| WO2000064877A1 (en) | 1999-04-26 | 2000-11-02 | Neurogen Corporation | 2-aminoquinolinecarboxamides: neurokinin receptor ligands |
| IT1320162B1 (it) | 2000-02-09 | 2003-11-18 | Rotta Research Lab | Derivati della tirosina ad attivita' anti leucotrienica, procedimentoper la loro preparazione e loro uso farmaceutico. |
| FI20002044A0 (fi) | 2000-09-15 | 2000-09-15 | Orion Yhtymae Oyj | Comt-entsyymiä estäviä naftaleenijohdannaisia |
| DE10110750A1 (de) | 2001-03-07 | 2002-09-12 | Bayer Ag | Neuartige Aminodicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| WO2002101073A2 (en) | 2001-06-13 | 2002-12-19 | Genesoft Pharmaceuticals, Inc. | Aryl-benzimidazole compounds having antiinfective activity |
| JP2005505507A (ja) | 2001-06-13 | 2005-02-24 | ジーンソフト ファーマシューティカルズ インコーポレイテッド | 抗感染活性を有するイソキノリン化合物 |
| US6762318B2 (en) | 2001-12-03 | 2004-07-13 | Novo Nordisk A/S | Glucagon antagonists |
| CN100522946C (zh) | 2001-12-06 | 2009-08-05 | 法布罗根股份有限公司 | 低氧诱导因子(HIF)α的稳定化 |
| US7618940B2 (en) | 2002-12-06 | 2009-11-17 | Fibrogen, Inc. | Fat regulation |
| US8124582B2 (en) | 2002-12-06 | 2012-02-28 | Fibrogen, Inc. | Treatment of diabetes |
| US8614204B2 (en) | 2003-06-06 | 2013-12-24 | Fibrogen, Inc. | Enhanced erythropoiesis and iron metabolism |
| WO2005007192A2 (en) | 2003-06-06 | 2005-01-27 | Fibrogen, Inc. | Cytoprotection through the use of hif hydroxylase inhibitors |
| CN103145616B (zh) | 2003-06-06 | 2015-09-30 | 菲布罗根有限公司 | 含氮杂芳基化合物及其在增加内源性促红细胞生成素中的用途 |
| US20060173046A1 (en) | 2003-07-15 | 2006-08-03 | Bell Ian M | Hydroxypyridine cgrp receptor antagonists |
| EP1658074B1 (en) | 2003-08-01 | 2012-11-07 | Fibrogen, Inc. | Inhibitors of 2-oxoglutarate dioxygenase as gamma globin inducers |
| JP2007501844A (ja) | 2003-08-08 | 2007-02-01 | トランス テック ファーマ，インコーポレイテッド | アリール及びヘテロアリール化合物、組成物並びに使用方法 |
| US7208601B2 (en) | 2003-08-08 | 2007-04-24 | Mjalli Adnan M M | Aryl and heteroaryl compounds, compositions, and methods of use |
| ES2332798T3 (es) | 2004-05-28 | 2010-02-12 | Fibrogen, Inc. | Ensayo de actividad de la prolil hidroxilasa de hif. |
| CN101166745A (zh) | 2005-03-02 | 2008-04-23 | 菲布罗根有限公司 | 噻吩并吡啶化合物和其使用方法 |
| JP5390184B2 (ja) | 2005-06-06 | 2014-01-15 | ファイブローゲン、インコーポレーテッド | 貧血の改良された治療方法 |
| CN101242817B (zh) | 2005-06-15 | 2016-08-31 | 菲布罗根公司 | HIF1α调节剂在治疗癌症中的用途 |
| WO2007082899A1 (en) | 2006-01-17 | 2007-07-26 | Vib Vzw | Inhibitors of prolyl-hydroxylase 1 for the treatment of skeletal muscle degeneration |
| EP2044028B1 (en) | 2006-01-27 | 2012-05-16 | Fibrogen, Inc. | Cyanoisoquinoline compounds that stabilize hypoxia inducible factor (hif) |
| BRPI0710527B8 (pt) | 2006-04-04 | 2021-05-25 | Fibrogen Inc | compostos de pirrolo- e tiazolo-piridina e composição farmacêutica que os compreende |
| US20070293575A1 (en) | 2006-06-15 | 2007-12-20 | Fibrogen, Inc. | Compounds and methods for treatment of cancer-related anemia |
| US7713986B2 (en) | 2006-06-15 | 2010-05-11 | Fibrogen, Inc. | Compounds and methods for treatment of chemotherapy-induced anemia |
| EP2044005B8 (en) * | 2006-06-26 | 2012-12-05 | Warner Chilcott Company, LLC | Prolyl hydroxylase inhibitors and methods of use |
| WO2009073669A1 (en) | 2007-12-03 | 2009-06-11 | Fibrogen, Inc. | Isoxazolopyridine derivatives for use in the treatment of hif-mediated conditions |
| US8952160B2 (en) | 2008-01-11 | 2015-02-10 | Fibrogen, Inc. | Isothiazole-pyridine derivatives as modulators of HIF (hypoxia inducible factor) activity |
| US8324405B2 (en) | 2008-02-05 | 2012-12-04 | Fibrogen, Inc. | Chromene derivatives and use thereof as HIF hydroxylase activity inhibitors |
| US8217043B2 (en) | 2008-08-20 | 2012-07-10 | Fibrogen, Inc. | Compounds and methods for their use |
| NZ592741A (en) | 2008-11-14 | 2013-03-28 | Fibrogen Inc | Thiochromene derivatives as hif hydroxylase inhibitors |
| JP5762971B2 (ja) | 2008-12-03 | 2015-08-12 | プレシディオ ファーマシューティカルズ インコーポレイテッド | Ｈｃｖｎｓ５ａの阻害剤 |
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