BRPI0806566A2 - Derivados de glicina n-substituída: inibidores de hidroxilase - Google Patents
Derivados de glicina n-substituída: inibidores de hidroxilase Download PDFInfo
- Publication number
- BRPI0806566A2 BRPI0806566A2 BRPI0806566-7A BRPI0806566A BRPI0806566A2 BR PI0806566 A2 BRPI0806566 A2 BR PI0806566A2 BR PI0806566 A BRPI0806566 A BR PI0806566A BR PI0806566 A2 BRPI0806566 A2 BR PI0806566A2
- Authority
- BR
- Brazil
- Prior art keywords
- oxo
- hydroxy
- dihydro
- glycine
- carbonyl
- Prior art date
Links
- 102000008109 Mixed Function Oxygenases Human genes 0.000 title 1
- 108010074633 Mixed Function Oxygenases Proteins 0.000 title 1
- 108010049175 N-substituted Glycines Proteins 0.000 title 1
- 150000002332 glycine derivatives Chemical class 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 61
- -1 -NR5R6 Chemical group 0.000 claims 55
- 125000001072 heteroaryl group Chemical group 0.000 claims 33
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 32
- 125000003118 aryl group Chemical group 0.000 claims 30
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 28
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 26
- 125000000217 alkyl group Chemical group 0.000 claims 19
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 18
- 150000002431 hydrogen Chemical group 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 10
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 10
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 9
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 8
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 125000002877 alkyl aryl group Chemical group 0.000 claims 7
- 125000005842 heteroatom Chemical group 0.000 claims 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 7
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 5
- 125000006725 C1-C10 alkenyl group Chemical group 0.000 claims 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 150000001768 cations Chemical class 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 239000012453 solvate Substances 0.000 claims 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 4
- 241000124008 Mammalia Species 0.000 claims 4
- 208000007502 anemia Diseases 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims 3
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 3
- 125000000267 glycino group Chemical group [H]N([*])C([H])([H])C(=O)O[H] 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims 2
- 102000004079 Prolyl Hydroxylases Human genes 0.000 claims 2
- 108010043005 Prolyl Hydroxylases Proteins 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000005059 halophenyl group Chemical group 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- 229910052717 sulfur Chemical group 0.000 claims 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims 1
- DWRGIUZLXHTJKW-UHFFFAOYSA-N 2-[(2-benzyl-5-hydroxy-3-oxo-6-phenylpyridazine-4-carbonyl)amino]acetic acid Chemical compound O=C1C(C(=O)NCC(=O)O)=C(O)C(C=2C=CC=CC=2)=NN1CC1=CC=CC=C1 DWRGIUZLXHTJKW-UHFFFAOYSA-N 0.000 claims 1
- MTJZXXIGRIUJEU-UHFFFAOYSA-N 2-[(2-benzyl-5-hydroxy-3-oxo-6-propan-2-ylpyridazine-4-carbonyl)amino]acetic acid Chemical compound O=C1C(C(=O)NCC(O)=O)=C(O)C(C(C)C)=NN1CC1=CC=CC=C1 MTJZXXIGRIUJEU-UHFFFAOYSA-N 0.000 claims 1
- VMQYMEKAPSRKMX-UHFFFAOYSA-N 2-[(4-hydroxy-6-oxo-3-phenyl-1h-pyridazine-5-carbonyl)amino]acetic acid Chemical compound N1C(=O)C(C(=O)NCC(=O)O)=C(O)C(C=2C=CC=CC=2)=N1 VMQYMEKAPSRKMX-UHFFFAOYSA-N 0.000 claims 1
- WRENSAXIPQHRGH-UHFFFAOYSA-N 2-[(6-tert-butyl-2-cyclohexyl-5-hydroxy-3-oxopyridazine-4-carbonyl)amino]acetic acid Chemical compound O=C1C(C(=O)NCC(O)=O)=C(O)C(C(C)(C)C)=NN1C1CCCCC1 WRENSAXIPQHRGH-UHFFFAOYSA-N 0.000 claims 1
- JSKPGEWZEVXBIQ-UHFFFAOYSA-N 2-[[2-(1,3-benzothiazol-2-ylmethyl)-5-hydroxy-3-oxo-6-propan-2-ylpyridazine-4-carbonyl]amino]acetic acid Chemical compound O=C1C(C(=O)NCC(O)=O)=C(O)C(C(C)C)=NN1CC1=NC2=CC=CC=C2S1 JSKPGEWZEVXBIQ-UHFFFAOYSA-N 0.000 claims 1
- FNSMXFOXZPNJEP-UHFFFAOYSA-N 2-[[2-(2-cyclopropylethyl)-5-hydroxy-3-oxo-6-phenylpyridazine-4-carbonyl]amino]acetic acid Chemical compound O=C1C(C(=O)NCC(=O)O)=C(O)C(C=2C=CC=CC=2)=NN1CCC1CC1 FNSMXFOXZPNJEP-UHFFFAOYSA-N 0.000 claims 1
- VDVLEQVPLSQREQ-UHFFFAOYSA-N 2-[[2-[(2-bromophenyl)methyl]-5-hydroxy-3-oxo-6-propan-2-ylpyridazine-4-carbonyl]amino]acetic acid Chemical compound O=C1C(C(=O)NCC(O)=O)=C(O)C(C(C)C)=NN1CC1=CC=CC=C1Br VDVLEQVPLSQREQ-UHFFFAOYSA-N 0.000 claims 1
- KDXBFIQIWOGQMC-UHFFFAOYSA-N 2-[[2-[(2-chlorophenyl)methyl]-6-cyclohexyl-5-hydroxy-3-oxopyridazine-4-carbonyl]amino]acetic acid Chemical compound O=C1C(C(=O)NCC(=O)O)=C(O)C(C2CCCCC2)=NN1CC1=CC=CC=C1Cl KDXBFIQIWOGQMC-UHFFFAOYSA-N 0.000 claims 1
- IMQPYVPFWOAQOP-UHFFFAOYSA-N 2-[[2-[(3-bromophenyl)methyl]-5-hydroxy-3-oxo-6-propan-2-ylpyridazine-4-carbonyl]amino]acetic acid Chemical compound O=C1C(C(=O)NCC(O)=O)=C(O)C(C(C)C)=NN1CC1=CC=CC(Br)=C1 IMQPYVPFWOAQOP-UHFFFAOYSA-N 0.000 claims 1
- ROFGRXZLIAMOFL-UHFFFAOYSA-N 2-[[2-[(3-cyanophenyl)methyl]-5-hydroxy-3-oxo-6-propan-2-ylpyridazine-4-carbonyl]amino]acetic acid Chemical compound O=C1C(C(=O)NCC(O)=O)=C(O)C(C(C)C)=NN1CC1=CC=CC(C#N)=C1 ROFGRXZLIAMOFL-UHFFFAOYSA-N 0.000 claims 1
- BPFLAJJDOYQJEP-UHFFFAOYSA-N 2-[[2-[(4-bromophenyl)methyl]-5-hydroxy-3-oxo-6-propan-2-ylpyridazine-4-carbonyl]amino]acetic acid Chemical compound O=C1C(C(=O)NCC(O)=O)=C(O)C(C(C)C)=NN1CC1=CC=C(Br)C=C1 BPFLAJJDOYQJEP-UHFFFAOYSA-N 0.000 claims 1
- JBVRDBFRATUHDD-UHFFFAOYSA-N 2-[[2-[(4-tert-butylphenyl)methyl]-6-cyclohexyl-5-hydroxy-3-oxopyridazine-4-carbonyl]amino]acetic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1CN1C(=O)C(C(=O)NCC(O)=O)=C(O)C(C2CCCCC2)=N1 JBVRDBFRATUHDD-UHFFFAOYSA-N 0.000 claims 1
- WSVNXZBCYPWRCQ-UHFFFAOYSA-N 2-[[2-[[2-(4-fluorophenyl)phenyl]methyl]-5-hydroxy-3-oxo-6-propan-2-ylpyridazine-4-carbonyl]amino]acetic acid Chemical compound O=C1C(C(=O)NCC(O)=O)=C(O)C(C(C)C)=NN1CC1=CC=CC=C1C1=CC=C(F)C=C1 WSVNXZBCYPWRCQ-UHFFFAOYSA-N 0.000 claims 1
- QBYVUMGLQABSAD-UHFFFAOYSA-N 2-[[2-[[2-fluoro-4-(4-nitrophenyl)phenyl]methyl]-5-hydroxy-3-oxo-6-propan-2-ylpyridazine-4-carbonyl]amino]acetic acid Chemical compound O=C1C(C(=O)NCC(O)=O)=C(O)C(C(C)C)=NN1CC1=CC=C(C=2C=CC(=CC=2)[N+]([O-])=O)C=C1F QBYVUMGLQABSAD-UHFFFAOYSA-N 0.000 claims 1
- SZKPZWMBMGCDDY-UHFFFAOYSA-N 2-[[2-[[2-fluoro-4-[4-(trifluoromethyl)phenyl]phenyl]methyl]-5-hydroxy-3-oxo-6-propan-2-ylpyridazine-4-carbonyl]amino]acetic acid Chemical compound O=C1C(C(=O)NCC(O)=O)=C(O)C(C(C)C)=NN1CC1=CC=C(C=2C=CC(=CC=2)C(F)(F)F)C=C1F SZKPZWMBMGCDDY-UHFFFAOYSA-N 0.000 claims 1
- UDOJUYSSRYDBNP-UHFFFAOYSA-N 2-[[2-[[4-(2,6-difluoropyridin-4-yl)phenyl]methyl]-5-hydroxy-3-oxo-6-propan-2-ylpyridazine-4-carbonyl]amino]acetic acid Chemical compound O=C1C(C(=O)NCC(O)=O)=C(O)C(C(C)C)=NN1CC1=CC=C(C=2C=C(F)N=C(F)C=2)C=C1 UDOJUYSSRYDBNP-UHFFFAOYSA-N 0.000 claims 1
- WEYGUQCGUQEXPD-UHFFFAOYSA-N 2-[[2-[[4-(4-fluorophenyl)phenyl]methyl]-5-hydroxy-3-oxo-6-propan-2-ylpyridazine-4-carbonyl]amino]acetic acid Chemical compound O=C1C(C(=O)NCC(O)=O)=C(O)C(C(C)C)=NN1CC1=CC=C(C=2C=CC(F)=CC=2)C=C1 WEYGUQCGUQEXPD-UHFFFAOYSA-N 0.000 claims 1
- INCXVGPAXTUQID-UHFFFAOYSA-N 2-[[2-benzyl-5-hydroxy-3-oxo-6-(trifluoromethyl)pyridazine-4-carbonyl]amino]acetic acid Chemical compound O=C1C(C(=O)NCC(=O)O)=C(O)C(C(F)(F)F)=NN1CC1=CC=CC=C1 INCXVGPAXTUQID-UHFFFAOYSA-N 0.000 claims 1
- PBPXHPGOPGLQCP-UHFFFAOYSA-N 2-[[5-hydroxy-2-[(2-nitrophenyl)methyl]-3-oxo-6-propan-2-ylpyridazine-4-carbonyl]amino]acetic acid Chemical compound O=C1C(C(=O)NCC(O)=O)=C(O)C(C(C)C)=NN1CC1=CC=CC=C1[N+]([O-])=O PBPXHPGOPGLQCP-UHFFFAOYSA-N 0.000 claims 1
- AHVSZWUPCCNAOZ-UHFFFAOYSA-N 2-[[5-hydroxy-2-[[2-(2-methoxyphenyl)phenyl]methyl]-3-oxo-6-propan-2-ylpyridazine-4-carbonyl]amino]acetic acid Chemical compound COC1=CC=CC=C1C1=CC=CC=C1CN1C(=O)C(C(=O)NCC(O)=O)=C(O)C(C(C)C)=N1 AHVSZWUPCCNAOZ-UHFFFAOYSA-N 0.000 claims 1
- ULIQJGDMWQPTAA-UHFFFAOYSA-N 2-[[5-hydroxy-2-[[2-(4-nitrophenyl)phenyl]methyl]-3-oxo-6-propan-2-ylpyridazine-4-carbonyl]amino]acetic acid Chemical compound O=C1C(C(=O)NCC(O)=O)=C(O)C(C(C)C)=NN1CC1=CC=CC=C1C1=CC=C([N+]([O-])=O)C=C1 ULIQJGDMWQPTAA-UHFFFAOYSA-N 0.000 claims 1
- ZVPVOVAZTUWNQD-UHFFFAOYSA-N 2-[[5-hydroxy-2-[[4-(2-methoxyphenyl)phenyl]methyl]-3-oxo-6-propan-2-ylpyridazine-4-carbonyl]amino]acetic acid Chemical compound COC1=CC=CC=C1C(C=C1)=CC=C1CN1C(=O)C(C(=O)NCC(O)=O)=C(O)C(C(C)C)=N1 ZVPVOVAZTUWNQD-UHFFFAOYSA-N 0.000 claims 1
- HEWKEZWYAMOPPW-UHFFFAOYSA-N 2-[[5-hydroxy-2-[[4-(4-nitrophenyl)phenyl]methyl]-3-oxo-6-propan-2-ylpyridazine-4-carbonyl]amino]acetic acid Chemical compound O=C1C(C(=O)NCC(O)=O)=C(O)C(C(C)C)=NN1CC1=CC=C(C=2C=CC(=CC=2)[N+]([O-])=O)C=C1 HEWKEZWYAMOPPW-UHFFFAOYSA-N 0.000 claims 1
- RWILEBQJSWJTJX-UHFFFAOYSA-N 2-[[5-hydroxy-3-oxo-2-[(2-phenylphenyl)methyl]-6-propan-2-ylpyridazine-4-carbonyl]amino]acetic acid Chemical compound O=C1C(C(=O)NCC(O)=O)=C(O)C(C(C)C)=NN1CC1=CC=CC=C1C1=CC=CC=C1 RWILEBQJSWJTJX-UHFFFAOYSA-N 0.000 claims 1
- NSFWBMSBBUIWNN-UHFFFAOYSA-N 2-[[5-hydroxy-3-oxo-2-[(3-phenylphenyl)methyl]-6-propan-2-ylpyridazine-4-carbonyl]amino]acetic acid Chemical compound O=C1C(C(=O)NCC(O)=O)=C(O)C(C(C)C)=NN1CC1=CC=CC(C=2C=CC=CC=2)=C1 NSFWBMSBBUIWNN-UHFFFAOYSA-N 0.000 claims 1
- SQXILEOCASCMHB-UHFFFAOYSA-N 2-[[5-hydroxy-3-oxo-2-[[2-(2-piperazin-1-ylpyridin-4-yl)phenyl]methyl]-6-propan-2-ylpyridazine-4-carbonyl]amino]acetic acid Chemical compound O=C1C(C(=O)NCC(O)=O)=C(O)C(C(C)C)=NN1CC1=CC=CC=C1C1=CC=NC(N2CCNCC2)=C1 SQXILEOCASCMHB-UHFFFAOYSA-N 0.000 claims 1
- USQQRSHNDHDDAD-UHFFFAOYSA-N 2-[[5-hydroxy-3-oxo-2-[[3-(2-piperazin-1-ylpyridin-4-yl)phenyl]methyl]-6-propan-2-ylpyridazine-4-carbonyl]amino]acetic acid Chemical compound O=C1C(C(=O)NCC(O)=O)=C(O)C(C(C)C)=NN1CC1=CC=CC(C=2C=C(N=CC=2)N2CCNCC2)=C1 USQQRSHNDHDDAD-UHFFFAOYSA-N 0.000 claims 1
- JWXMUUZCFGXCRK-UHFFFAOYSA-N 2-[[5-hydroxy-3-oxo-2-[[4-(2-piperazin-1-ylpyridin-4-yl)phenyl]methyl]-6-propan-2-ylpyridazine-4-carbonyl]amino]acetic acid Chemical compound O=C1C(C(=O)NCC(O)=O)=C(O)C(C(C)C)=NN1CC1=CC=C(C=2C=C(N=CC=2)N2CCNCC2)C=C1 JWXMUUZCFGXCRK-UHFFFAOYSA-N 0.000 claims 1
- UIKSNTQBBOLXKX-UHFFFAOYSA-N 2-[[5-hydroxy-3-oxo-6-phenyl-2-(2-phenylethyl)pyridazine-4-carbonyl]amino]acetic acid Chemical compound O=C1C(C(=O)NCC(=O)O)=C(O)C(C=2C=CC=CC=2)=NN1CCC1=CC=CC=C1 UIKSNTQBBOLXKX-UHFFFAOYSA-N 0.000 claims 1
- HGYSLVHGPRECQQ-UHFFFAOYSA-N 2-[[5-hydroxy-3-oxo-6-propan-2-yl-2-[(4-pyridin-4-ylphenyl)methyl]pyridazine-4-carbonyl]amino]acetic acid Chemical compound O=C1C(C(=O)NCC(O)=O)=C(O)C(C(C)C)=NN1CC1=CC=C(C=2C=CN=CC=2)C=C1 HGYSLVHGPRECQQ-UHFFFAOYSA-N 0.000 claims 1
- TZXVCSJGARFVLZ-UHFFFAOYSA-N 2-[[5-hydroxy-3-oxo-6-propan-2-yl-2-[[2-[4-(trifluoromethyl)phenyl]phenyl]methyl]pyridazine-4-carbonyl]amino]acetic acid Chemical compound O=C1C(C(=O)NCC(O)=O)=C(O)C(C(C)C)=NN1CC1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 TZXVCSJGARFVLZ-UHFFFAOYSA-N 0.000 claims 1
- JSVCSRRGEWVMFF-UHFFFAOYSA-N 2-[[5-hydroxy-6-methyl-2-[(2-nitrophenyl)methyl]-3-oxopyridazine-4-carbonyl]amino]acetic acid Chemical compound O=C1C(C(=O)NCC(O)=O)=C(O)C(C)=NN1CC1=CC=CC=C1[N+]([O-])=O JSVCSRRGEWVMFF-UHFFFAOYSA-N 0.000 claims 1
- BMEBRCIDAGDITE-UHFFFAOYSA-N 2-[[6-(carboxymethylcarbamoyl)-2-[(2-chlorophenyl)methyl]-5-hydroxy-3-oxopyridazine-4-carbonyl]amino]acetic acid Chemical compound O=C1C(C(=O)NCC(O)=O)=C(O)C(C(=O)NCC(=O)O)=NN1CC1=CC=CC=C1Cl BMEBRCIDAGDITE-UHFFFAOYSA-N 0.000 claims 1
- PYFJJMYGWHYEDN-UHFFFAOYSA-N 2-[[6-cyclohexyl-5-hydroxy-2-[(2-methylphenyl)methyl]-3-oxopyridazine-4-carbonyl]amino]acetic acid Chemical compound CC1=CC=CC=C1CN1C(=O)C(C(=O)NCC(O)=O)=C(O)C(C2CCCCC2)=N1 PYFJJMYGWHYEDN-UHFFFAOYSA-N 0.000 claims 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- PFKITESTTSWHMP-UHFFFAOYSA-N 3-fluoro-4-phenylbenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 PFKITESTTSWHMP-UHFFFAOYSA-N 0.000 claims 1
- 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 claims 1
- 239000004471 Glycine Substances 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims 1
- 150000005215 alkyl ethers Chemical class 0.000 claims 1
- 235000008206 alpha-amino acids Nutrition 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 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 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- 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 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Enzymes And Modification Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88471007P | 2007-01-12 | 2007-01-12 | |
| US60/884.710 | 2007-01-12 | ||
| PCT/US2008/050833 WO2008089052A2 (en) | 2007-01-12 | 2008-01-11 | N-substituted glycine derivatives: hydroxylase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BRPI0806566A2 true BRPI0806566A2 (pt) | 2014-05-06 |
Family
ID=39636631
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0806566-7A BRPI0806566A2 (pt) | 2007-01-12 | 2008-01-11 | Derivados de glicina n-substituída: inibidores de hidroxilase |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US7608621B2 (enExample) |
| EP (2) | EP2889289B1 (enExample) |
| JP (1) | JP5313925B2 (enExample) |
| KR (1) | KR101458655B1 (enExample) |
| CN (1) | CN101626685B (enExample) |
| AR (1) | AR064878A1 (enExample) |
| AU (1) | AU2008206441B2 (enExample) |
| BR (1) | BRPI0806566A2 (enExample) |
| CA (1) | CA2675252C (enExample) |
| CL (1) | CL2008000066A1 (enExample) |
| DK (1) | DK2124565T3 (enExample) |
| EA (1) | EA017112B1 (enExample) |
| ES (2) | ES2614355T3 (enExample) |
| HR (1) | HRP20150119T1 (enExample) |
| MX (1) | MX2009007548A (enExample) |
| PL (1) | PL2124565T3 (enExample) |
| PT (1) | PT2124565E (enExample) |
| SI (1) | SI2124565T1 (enExample) |
| TW (1) | TW200845991A (enExample) |
| WO (1) | WO2008089052A2 (enExample) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR040672A1 (es) * | 2002-07-25 | 2005-04-13 | Glaxo Group Ltd | Forma de dosificacion farmaceutica multicomponenete, cuerpo apropiado para ser utilizado en la misma y procedimiento para prepararla |
| CN101212967A (zh) | 2005-05-10 | 2008-07-02 | 因塞特公司 | 吲哚胺2,3-双加氧酶调节剂及其用法 |
| ITMI20051085A1 (it) * | 2005-06-10 | 2006-12-11 | Acs Dobfar Spa | Metodo di purificazione del cefotetan |
| ES2540561T3 (es) | 2005-12-20 | 2015-07-10 | Incyte Corporation | N-hidroxiamidinoheterociclos como moduladores de indolamina 2,3-dioxigenasa |
| US7588924B2 (en) | 2006-03-07 | 2009-09-15 | Procter & Gamble Company | Crystal of hypoxia inducible factor 1 alpha prolyl hydroxylase |
| AU2007265460B2 (en) | 2006-06-26 | 2011-03-03 | Akebia Therapeutics Inc. | Prolyl hydroxylase inhibitors and methods of use |
| CA2663057C (en) * | 2006-09-19 | 2015-12-08 | Incyte Corporation | N-hydroxyamidinoheterocycles as modulators of indoleamine 2,3-dioxygenase |
| CL2007002650A1 (es) | 2006-09-19 | 2008-02-08 | Incyte Corp | Compuestos derivados de heterociclo n-hidroxiamino; composicion farmaceutica, util para tratar cancer, infecciones virales y desordenes neurodegenerativos entre otras. |
| US8952160B2 (en) | 2008-01-11 | 2015-02-10 | Fibrogen, Inc. | Isothiazole-pyridine derivatives as modulators of HIF (hypoxia inducible factor) activity |
| WO2009100250A1 (en) | 2008-02-05 | 2009-08-13 | Fibrogen, Inc. | Chromene derivatives and use thereof as hif hydroxylase activity inhibitors |
| PT2294066E (pt) | 2008-04-28 | 2014-11-21 | Janssen Pharmaceutica Nv | Benzoimidazoles como inibidores da prolil-hidroxilase |
| CN104042611B (zh) | 2008-07-08 | 2019-05-14 | 因塞特控股公司 | 作为吲哚胺2，3-双加氧酶的抑制剂的1，2，5-噁二唑 |
| EP2334682B1 (en) | 2008-08-20 | 2017-10-04 | Fibrogen, Inc. | Pyrrolo [ 1, 2 -b] pyridazine derivatives and their use as hif modulators |
| EP2326179A4 (en) * | 2008-08-25 | 2011-08-17 | Smithkline Beecham Corp | PROLYLHYDROXYLASEHEMMER |
| JP5631741B2 (ja) * | 2008-11-13 | 2014-11-26 | 日本農薬株式会社 | ピラジン誘導体類の製造方法及びその中間体類 |
| CN105037323A (zh) | 2008-11-14 | 2015-11-11 | 菲布罗根有限公司 | 作为hif羟化酶抑制剂的苯并噻喃衍生物 |
| DE102009004061A1 (de) * | 2009-01-08 | 2010-07-15 | Merck Patent Gmbh | Pyridazinonderivate |
| AR077417A1 (es) * | 2009-07-17 | 2011-08-24 | Japan Tobacco Inc | Compuesto triazolopiridina y su accion como inhibidor de prolil hidroxilasa o agente inductor de la produccion de eritropoyetina |
| WO2011048611A1 (en) * | 2009-10-07 | 2011-04-28 | Torrent Pharmaceuticals Limited | Novel fused pyridazine derivatives |
| RS54323B1 (sr) * | 2009-10-21 | 2016-02-29 | Daiichi Sankyo Company, Limited | Derivat 5-hidroksipirimidin-4-karboksamida |
| PH12012500788A1 (en) | 2009-11-06 | 2016-07-27 | Aerpio Therapeutics Inc | Compositions and methods for treating colitis |
| WO2011115687A2 (en) * | 2010-03-19 | 2011-09-22 | Northwestern University | Alkylated sp-b peptoid compounds and related lung surfactant compositions |
| CN103608346B (zh) | 2011-02-02 | 2016-06-15 | 菲布罗根有限公司 | 作为缺氧诱导因子(hif)羟化酶抑制剂的萘啶衍生物 |
| GB201102659D0 (en) | 2011-02-15 | 2011-03-30 | Isis Innovation | Assay |
| US8865748B2 (en) | 2011-06-06 | 2014-10-21 | Akebia Therapeutics Inc. | Compounds and compositions for stabilizing hypoxia inducible factor-2 alpha as a method for treating cancer |
| NO2686520T3 (enExample) | 2011-06-06 | 2018-03-17 | ||
| GB201113101D0 (en) | 2011-07-28 | 2011-09-14 | Isis Innovation | Assay |
| BR112014009910B1 (pt) | 2011-10-25 | 2020-06-30 | Janssen Pharmaceutica N.V. | sal di-hidrato de meglumina de ácido 1-(5,6-dicloro-1h-benzo[d]imidazol-2-il)-1h-pirazol-4-carboxílico, composição farmacêuticae pomada tópica |
| IN2015DN01035A (enExample) | 2012-07-30 | 2015-06-26 | Taisho Pharmaceutical Co Ltd | |
| MY204336A (en) | 2013-06-13 | 2024-08-23 | Akebia Therapeutics Inc | Compositions and methods for treating anemia |
| MY174254A (en) | 2013-11-08 | 2020-04-01 | Incyte Holdings Corp | Process for the synthesis of an indoleamine 2,3-dioxygenase inhibitor |
| CN114890943A (zh) | 2013-11-15 | 2022-08-12 | 阿克比治疗有限公司 | {[5-(3-氯苯基)-3-羟基吡啶-2-羰基]氨基}乙酸固体形式，组合物和用途 |
| EP3190104B1 (en) | 2014-09-02 | 2021-10-27 | Sunshine Lake Pharma Co., Ltd. | Quinolinone compound and use thereof |
| AU2016209126A1 (en) | 2015-01-23 | 2017-08-10 | Akebia Therapeutics, Inc. | Solid forms of 2-(5-(3-fluorophenyl)-3-hydroxypicolinamido)acetic acid, compositions, and uses thereof |
| UA123308C2 (uk) | 2015-04-01 | 2021-03-17 | Екебіа Терапьютікс, Інк. | Композиції і способи для лікування анемії |
| CN105130888A (zh) * | 2015-10-09 | 2015-12-09 | 中国药科大学 | 炔基吡啶类脯氨酰羟化酶抑制剂、其制备方法和医药用途 |
| CA3001065A1 (en) | 2015-10-14 | 2017-04-20 | Xiaoxi WEI | Compositions and methods for reducing ice crystal formation |
| MX2020011845A (es) | 2018-05-09 | 2021-01-15 | Akebia Therapeutics Inc | Proceso para preparar acido 2-[[5-(3-clorofenil)-3-hidroxipiridina -2-carbonil]amino]acetico. |
| US11524939B2 (en) | 2019-11-13 | 2022-12-13 | Akebia Therapeutics, Inc. | Solid forms of {[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino} acetic acid |
| WO2021127273A1 (en) * | 2019-12-20 | 2021-06-24 | Gb004, Inc. | 1 -((6-oxo-1,6-dihydropyridazin-4-yl)methyl)piperazine and 1 -((6-oxo-1,6-dihydropyrimidin-4-yl)methyl)piperazine derivatives as prolyl hydroxylase, hif-1 alpha and pgk modulators for use in treating inflammatory diseases, cancer or infections |
| WO2022179967A1 (en) | 2021-02-23 | 2022-09-01 | Glaxosmithkline Intellectual Property (No.2) Limited | Vadadustat for treating covid-19 in a hospitalized subject |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0650960B1 (de) | 1993-11-02 | 1997-03-05 | Hoechst Aktiengesellschaft | Substituierte heterocyclische Carbonsäureamidester, 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 |
| GB9507318D0 (en) * | 1995-04-07 | 1995-05-31 | Zeneca Ltd | Alpha substituted pyridazino quinoline compounds |
| US6972296B2 (en) * | 1999-05-07 | 2005-12-06 | Encysive Pharmaceuticals Inc. | Carboxylic acid derivatives that inhibit the binding of integrins to their receptors |
| DE10059418A1 (de) | 2000-11-30 | 2002-06-20 | Aventis Pharma Gmbh | Ortho, meta-substituierte Bisarylverbindungen, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament sowie sie enthaltende pharmazeutische Zubereitungen |
| US20030176317A1 (en) | 2001-12-06 | 2003-09-18 | Volkmar Guenzler-Pukall | Stabilization of hypoxia inducible factor (HIF) alpha |
| US6878709B2 (en) * | 2002-01-04 | 2005-04-12 | Schering Corporation | 3,4-di-substituted pyridazinediones as CXC chemokine receptor antagonists |
| WO2003088917A2 (en) | 2002-04-19 | 2003-10-30 | Vertex Pharmaceuticals Incorporated | Regulation of tnf-alpha |
| US8614204B2 (en) | 2003-06-06 | 2013-12-24 | Fibrogen, Inc. | Enhanced erythropoiesis and iron metabolism |
| US7718624B2 (en) | 2004-09-01 | 2010-05-18 | Sitkovsky Michail V | Modulation of immune response and inflammation by targeting hypoxia inducible factors |
| EP1655283A1 (en) | 2004-11-08 | 2006-05-10 | Evotec OAI AG | 11beta-HSD1 Inhibitors |
| 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 |
| 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 |
| WO2008013838A2 (en) | 2006-07-25 | 2008-01-31 | Cephalon, Inc. | Pyridizinone derivatives |
| US20090011051A1 (en) | 2006-09-28 | 2009-01-08 | Roth Mark B | Methods, Compositions and Articles of Manufacture for HIF Modulating Compounds |
| WO2008073292A2 (en) | 2006-12-08 | 2008-06-19 | Caritas St. Elizabeth's Medical Center Of Boston, Inc. | Method for protecting renal tubular epithelial cells from radiocontrast nephro parhy (rcn) |
| EP2328586A2 (en) | 2008-05-20 | 2011-06-08 | Cephalon, Inc. | Substituted pyridazinone derivatives as histamine-3 (h3) receptor ligands |
-
2008
- 2008-01-10 TW TW097100936A patent/TW200845991A/zh unknown
- 2008-01-10 CL CL200800066A patent/CL2008000066A1/es unknown
- 2008-01-11 PL PL08727581T patent/PL2124565T3/pl unknown
- 2008-01-11 US US11/972,702 patent/US7608621B2/en not_active Ceased
- 2008-01-11 ES ES14196983.2T patent/ES2614355T3/es active Active
- 2008-01-11 EA EA200970680A patent/EA017112B1/ru not_active IP Right Cessation
- 2008-01-11 EP EP14196983.2A patent/EP2889289B1/en active Active
- 2008-01-11 MX MX2009007548A patent/MX2009007548A/es active IP Right Grant
- 2008-01-11 AU AU2008206441A patent/AU2008206441B2/en not_active Ceased
- 2008-01-11 HR HRP20150119TT patent/HRP20150119T1/hr unknown
- 2008-01-11 BR BRPI0806566-7A patent/BRPI0806566A2/pt not_active IP Right Cessation
- 2008-01-11 DK DK08727581.4T patent/DK2124565T3/en active
- 2008-01-11 CN CN2008800073024A patent/CN101626685B/zh not_active Expired - Fee Related
- 2008-01-11 PT PT08727581T patent/PT2124565E/pt unknown
- 2008-01-11 EP EP08727581.4A patent/EP2124565B1/en active Active
- 2008-01-11 ES ES08727581.4T patent/ES2528745T3/es active Active
- 2008-01-11 CA CA2675252A patent/CA2675252C/en active Active
- 2008-01-11 JP JP2009545699A patent/JP5313925B2/ja active Active
- 2008-01-11 KR KR1020097016748A patent/KR101458655B1/ko active Active
- 2008-01-11 WO PCT/US2008/050833 patent/WO2008089052A2/en not_active Ceased
- 2008-01-11 AR ARP080100143A patent/AR064878A1/es active IP Right Grant
- 2008-01-11 SI SI200831409T patent/SI2124565T1/sl unknown
-
2011
- 2011-10-26 US US13/281,965 patent/USRE44613E1/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP2124565B1 (en) | 2015-01-07 |
| KR20090101376A (ko) | 2009-09-25 |
| JP5313925B2 (ja) | 2013-10-09 |
| MX2009007548A (es) | 2009-07-22 |
| US20080214549A1 (en) | 2008-09-04 |
| USRE44613E1 (en) | 2013-11-26 |
| KR101458655B1 (ko) | 2014-11-05 |
| CN101626685A (zh) | 2010-01-13 |
| CL2008000066A1 (es) | 2008-08-01 |
| WO2008089052A3 (en) | 2008-09-18 |
| AU2008206441B2 (en) | 2014-06-19 |
| EP2124565A2 (en) | 2009-12-02 |
| EP2124565A4 (en) | 2011-06-29 |
| EA200970680A1 (ru) | 2010-02-26 |
| EA017112B1 (ru) | 2012-09-28 |
| CA2675252A1 (en) | 2008-07-24 |
| EP2889289A1 (en) | 2015-07-01 |
| AR064878A1 (es) | 2009-04-29 |
| CN101626685B (zh) | 2013-03-13 |
| PL2124565T3 (pl) | 2015-05-29 |
| JP2010515756A (ja) | 2010-05-13 |
| CA2675252C (en) | 2015-05-26 |
| EP2889289B1 (en) | 2016-12-21 |
| US7608621B2 (en) | 2009-10-27 |
| ES2614355T3 (es) | 2017-05-30 |
| PT2124565E (pt) | 2015-03-26 |
| SI2124565T1 (sl) | 2015-04-30 |
| DK2124565T3 (en) | 2015-02-09 |
| TW200845991A (en) | 2008-12-01 |
| WO2008089052A2 (en) | 2008-07-24 |
| HRP20150119T1 (hr) | 2015-05-08 |
| ES2528745T3 (es) | 2015-02-12 |
| AU2008206441A1 (en) | 2008-07-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| BRPI0806566A2 (pt) | Derivados de glicina n-substituída: inibidores de hidroxilase | |
| JP5203361B2 (ja) | プロリルヒドロキシラーゼ阻害剤 | |
| US20110144167A1 (en) | Prolyl Hydroxylase Inhibitors | |
| EP2273879A1 (en) | Prolyl hydroxylase inhibitors | |
| US20110098324A1 (en) | Prolyl hydroxylase inhibitors | |
| SK279472B6 (sk) | Fenoxy- a fenoxyalkylpiperidíny, farmaceutický pro | |
| WO2010059555A1 (en) | Prolyl hydroxylase inhibitors | |
| HK1130671B (en) | Prolyl hydroxylase inhibitors |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B08L | Patent application lapsed because of non payment of annual fee [chapter 8.12 patent gazette] |
Free format text: REFERENTE AO NAO RECOLHIMENTO DAS 5A E 6A ANUIDADES. |
|
| B08I | Publication cancelled [chapter 8.9 patent gazette] |
Free format text: ANULADA A PUBLICACAO CODIGO 8.12 NA RPI NO 2277 DE 26/08/2014 POR TER SIDO INDEVIDA. |
|
| B08F | Application dismissed because of non-payment of annual fees [chapter 8.6 patent gazette] |
Free format text: REFERENTE AS 5A, 6A, 7A, 8A, 9A, 10A, 11A E 12A ANUIDADES. |
|
| B08K | Patent lapsed as no evidence of payment of the annual fee has been furnished to inpi [chapter 8.11 patent gazette] |
Free format text: EM VIRTUDE DO ARQUIVAMENTO PUBLICADO NA RPI 2602 DE 17-11-2020 E CONSIDERANDO AUSENCIA DE MANIFESTACAO DENTRO DOS PRAZOS LEGAIS, INFORMO QUE CABE SER MANTIDO O ARQUIVAMENTO DO PEDIDO DE PATENTE, CONFORME O DISPOSTO NO ARTIGO 12, DA RESOLUCAO 113/2013. |