HRP20120697T1 - Derivati aminonikotinske i izonikotinske kiseline kao inhibitori dihidroorotat dehidrogenaze (dhodh) - Google Patents
Derivati aminonikotinske i izonikotinske kiseline kao inhibitori dihidroorotat dehidrogenaze (dhodh) Download PDFInfo
- Publication number
- HRP20120697T1 HRP20120697T1 HRP20120697TT HRP20120697T HRP20120697T1 HR P20120697 T1 HRP20120697 T1 HR P20120697T1 HR P20120697T T HRP20120697T T HR P20120697TT HR P20120697 T HRP20120697 T HR P20120697T HR P20120697 T1 HRP20120697 T1 HR P20120697T1
- Authority
- HR
- Croatia
- Prior art keywords
- ylamino
- nicotinic acid
- groups
- group
- atoms
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title claims 4
- KPIVDNYJNOPGBE-UHFFFAOYSA-N 2-aminonicotinic acid Chemical compound NC1=NC=CC=C1C(O)=O KPIVDNYJNOPGBE-UHFFFAOYSA-N 0.000 title 1
- 101150102768 Dhodh gene Proteins 0.000 title 1
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical class OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 title 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 28
- 125000001424 substituent group Chemical group 0.000 claims abstract 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 21
- 229910052736 halogen Inorganic materials 0.000 claims abstract 19
- 150000002367 halogens Chemical class 0.000 claims abstract 19
- 125000004429 atom Chemical group 0.000 claims abstract 17
- 150000001875 compounds Chemical class 0.000 claims abstract 17
- 125000005843 halogen group Chemical group 0.000 claims abstract 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 9
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract 5
- 150000001204 N-oxides Chemical class 0.000 claims abstract 2
- 150000001768 cations Chemical class 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 7
- -1 2-(3'-(difluoromethoxy)-3-fluorobiphenyl-4-ylamino)nicotinic acid 2-(3'-cyclobutoxy-3-fluorobiphenyl-4-ylamino)nicotinic acid 2-(3-fluoro-3'-(2,2,2-trifluoroethoxy)biphenyl-4-ylamino)nicotinic acid Chemical compound 0.000 claims 6
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 6
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 5
- 229910052731 fluorine Inorganic materials 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 229960003512 nicotinic acid Drugs 0.000 claims 3
- 235000001968 nicotinic acid Nutrition 0.000 claims 3
- 239000011664 nicotinic acid Substances 0.000 claims 3
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 108010057466 NF-kappa B Proteins 0.000 claims 2
- 102100023050 Nuclear factor NF-kappa-B p105 subunit Human genes 0.000 claims 2
- 108010022394 Threonine synthase Proteins 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 102000004419 dihydrofolate reductase Human genes 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 239000011737 fluorine Chemical group 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 230000001575 pathological effect Effects 0.000 claims 2
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 claims 1
- HMLGSIZOMSVISS-ONJSNURVSA-N (7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2,2-dimethylpropanoyloxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N([C@@H]1C(N2C(=C(C=C)CSC21)C(O)=O)=O)C(=O)\C(=N/OCOC(=O)C(C)(C)C)C1=CSC(N)=N1 HMLGSIZOMSVISS-ONJSNURVSA-N 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- BCHNLTZCBVSKBT-UHFFFAOYSA-N 2-[2,5-difluoro-4-(3-methoxyphenyl)anilino]pyridine-3-carboxylic acid 2-[4-(3-ethoxyphenyl)-2-(trifluoromethoxy)anilino]pyridine-3-carboxylic acid 2-[4-(3-methoxyphenyl)-2-(trifluoromethoxy)anilino]pyridine-3-carboxylic acid Chemical compound FC1=C(C=C(C(=C1)NC1=C(C(=O)O)C=CC=N1)F)C1=CC(=CC=C1)OC.COC=1C=C(C=CC1)C1=CC(=C(C=C1)NC1=C(C(=O)O)C=CC=N1)OC(F)(F)F.C(C)OC=1C=C(C=CC1)C1=CC(=C(C=C1)NC1=C(C(=O)O)C=CC=N1)OC(F)(F)F BCHNLTZCBVSKBT-UHFFFAOYSA-N 0.000 claims 1
- ADUJLGYSXJXSKA-UHFFFAOYSA-N 2-[4-(3-ethoxyphenyl)-2-fluoro-5-methylanilino]pyridine-3-carboxylic acid Chemical compound CCOC1=CC=CC(C=2C(=CC(NC=3C(=CC=CN=3)C(O)=O)=C(F)C=2)C)=C1 ADUJLGYSXJXSKA-UHFFFAOYSA-N 0.000 claims 1
- PBHOIGKTJNMGLS-UHFFFAOYSA-N 2-[4-(3-ethoxyphenyl)-2-fluoroanilino]pyridine-3-carboxylic acid;2-[2-fluoro-4-(3-methoxyphenyl)anilino]pyridine-3-carboxylic acid;2-[2-fluoro-4-[3-(trifluoromethoxy)phenyl]anilino]pyridine-3-carboxylic acid Chemical compound COC1=CC=CC(C=2C=C(F)C(NC=3C(=CC=CN=3)C(O)=O)=CC=2)=C1.CCOC1=CC=CC(C=2C=C(F)C(NC=3C(=CC=CN=3)C(O)=O)=CC=2)=C1.OC(=O)C1=CC=CN=C1NC1=CC=C(C=2C=C(OC(F)(F)F)C=CC=2)C=C1F PBHOIGKTJNMGLS-UHFFFAOYSA-N 0.000 claims 1
- WFJRAFKYOTVRJI-UHFFFAOYSA-N 2-[4-(3-ethoxyphenyl)anilino]pyridine-3-carboxylic acid 2-[2-fluoro-5-methyl-4-[3-(trifluoromethoxy)phenyl]anilino]pyridine-3-carboxylic acid 3-[2-fluoro-4-[3-(trifluoromethoxy)phenyl]anilino]pyridine-4-carboxylic acid Chemical compound FC=1C(=CC(=C(C1)C1=CC(=CC=C1)OC(F)(F)F)C)NC1=C(C(=O)O)C=CC=N1.C(C)OC=1C=C(C=CC1)C1=CC=C(C=C1)NC1=C(C(=O)O)C=CC=N1.FC=1C=C(C=CC1NC1=C(C(=O)O)C=CN=C1)C1=CC(=CC=C1)OC(F)(F)F WFJRAFKYOTVRJI-UHFFFAOYSA-N 0.000 claims 1
- JBNWDYGOTHQHOZ-UHFFFAOYSA-N 2-[5-[4-[(4-fluorophenyl)methyl]piperidine-1-carbonyl]-6-methoxy-1-methylindol-3-yl]-n,n-dimethyl-2-oxoacetamide Chemical compound COC1=CC=2N(C)C=C(C(=O)C(=O)N(C)C)C=2C=C1C(=O)N(CC1)CCC1CC1=CC=C(F)C=C1 JBNWDYGOTHQHOZ-UHFFFAOYSA-N 0.000 claims 1
- RQVKVJIRFKVPBF-VWLOTQADSA-N 2-[[(2s)-2-amino-3-phenylpropyl]amino]-3-methyl-5-naphthalen-2-yl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C([C@H](N)CNC=1N(C(C(C=2C=C3C=CC=CC3=CC=2)=C(C=2C=CN=CC=2)N=1)=O)C)C1=CC=CC=C1 RQVKVJIRFKVPBF-VWLOTQADSA-N 0.000 claims 1
- NAWXUBYGYWOOIX-UHFFFAOYSA-N 2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)NC(CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-UHFFFAOYSA-N 0.000 claims 1
- CYHGOYZERGCKJC-UHFFFAOYSA-N 3-[4-(3-cyclopropyloxyphenyl)-2-fluoroanilino]pyridine-4-carboxylic acid;2-[2,6-difluoro-4-(2-methylphenyl)anilino]pyridine-3-carboxylic acid;2-[2,3,5,6-tetrafluoro-4-(3-methoxyphenyl)anilino]pyridine-3-carboxylic acid Chemical compound CC1=CC=CC=C1C(C=C1F)=CC(F)=C1NC1=NC=CC=C1C(O)=O.OC(=O)C1=CC=NC=C1NC1=CC=C(C=2C=C(OC3CC3)C=CC=2)C=C1F.COC1=CC=CC(C=2C(=C(F)C(NC=3C(=CC=CN=3)C(O)=O)=C(F)C=2F)F)=C1 CYHGOYZERGCKJC-UHFFFAOYSA-N 0.000 claims 1
- QSUSKMBNZQHHPA-UHFFFAOYSA-N 4-[4-(4-fluorophenyl)-1-(3-phenylpropyl)-5-pyridin-4-ylimidazol-2-yl]but-3-yn-1-ol Chemical compound C=1C=CC=CC=1CCCN1C(C#CCCO)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=NC=C1 QSUSKMBNZQHHPA-UHFFFAOYSA-N 0.000 claims 1
- TVZGACDUOSZQKY-LBPRGKRZSA-N 4-aminofolic acid Chemical compound C1=NC2=NC(N)=NC(N)=C2N=C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 TVZGACDUOSZQKY-LBPRGKRZSA-N 0.000 claims 1
- IFGWYHGYNVGVRB-UHFFFAOYSA-N 5-(2,4-difluorophenoxy)-n-[2-(dimethylamino)ethyl]-1-(2-methylpropyl)indazole-6-carboxamide Chemical compound CN(C)CCNC(=O)C=1C=C2N(CC(C)C)N=CC2=CC=1OC1=CC=C(F)C=C1F IFGWYHGYNVGVRB-UHFFFAOYSA-N 0.000 claims 1
- ZCMLDRXBGGOAPZ-UHFFFAOYSA-N 5-bromo-2-[2-fluoro-4-[3-(trifluoromethoxy)phenyl]anilino]pyridine-3-carboxylic acid 2-[2-fluoro-4-[3-(trifluoromethoxy)phenyl]anilino]-5-methylpyridine-3-carboxylic acid Chemical compound FC=1C=C(C=CC1NC1=C(C(=O)O)C=C(C=N1)C)C1=CC(=CC=C1)OC(F)(F)F.BrC=1C=NC(=C(C(=O)O)C1)NC1=C(C=C(C=C1)C1=CC(=CC=C1)OC(F)(F)F)F ZCMLDRXBGGOAPZ-UHFFFAOYSA-N 0.000 claims 1
- LMBRAWXFEYTROA-UHFFFAOYSA-N 5-chloro-2-[2,6-difluoro-4-(3-methoxyphenyl)anilino]pyridine-3-carboxylic acid Chemical compound COC1=CC=CC(C=2C=C(F)C(NC=3C(=CC(Cl)=CN=3)C(O)=O)=C(F)C=2)=C1 LMBRAWXFEYTROA-UHFFFAOYSA-N 0.000 claims 1
- JUFWWKDBQNPWJI-UHFFFAOYSA-N 5-cyclopropyl-2-[2,6-difluoro-4-[3-(trifluoromethoxy)phenyl]anilino]pyridine-3-carboxylic acid 2-[2,3,6-trifluoro-4-(3-methoxyphenyl)anilino]pyridine-3-carboxylic acid Chemical compound FC1=C(C=C(C(=C1F)NC1=C(C(=O)O)C=CC=N1)F)C1=CC(=CC=C1)OC.C1(CC1)C=1C=NC(=C(C(=O)O)C1)NC1=C(C=C(C=C1F)C1=CC(=CC=C1)OC(F)(F)F)F JUFWWKDBQNPWJI-UHFFFAOYSA-N 0.000 claims 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 1
- JMPGFABCOMUHGX-UHFFFAOYSA-N BrC=1C=NC(=C(C(=O)O)C1)NC1=C(C=C(C=C1F)C1=CC(=CC=C1)OC)F.BrC=1C=NC(=C(C(=O)O)C1)NC1=C(C=C(C=C1)C1=CC(=CC=C1)OC)F Chemical compound BrC=1C=NC(=C(C(=O)O)C1)NC1=C(C=C(C=C1F)C1=CC(=CC=C1)OC)F.BrC=1C=NC(=C(C(=O)O)C1)NC1=C(C=C(C=C1)C1=CC(=CC=C1)OC)F JMPGFABCOMUHGX-UHFFFAOYSA-N 0.000 claims 1
- RHFOKNXIKABGNE-UHFFFAOYSA-N BrC=1C=NC(=C(C(=O)O)C1)NC1=CC(=C(C=C1F)C1=CC(=CC=C1)OCC)F.FC=1C=C(C=C(C1NC1=C(C(=O)O)C=C(C=N1)CC)F)C1=CC(=CC=C1)OC Chemical compound BrC=1C=NC(=C(C(=O)O)C1)NC1=CC(=C(C=C1F)C1=CC(=CC=C1)OCC)F.FC=1C=C(C=C(C1NC1=C(C(=O)O)C=C(C=N1)CC)F)C1=CC(=CC=C1)OC RHFOKNXIKABGNE-UHFFFAOYSA-N 0.000 claims 1
- UKFJCCOIDYIESK-UHFFFAOYSA-N C1(CC1)C=1C=NC(=C(C(=O)O)C1)NC1=C(C=C(C=C1F)C1=CC(=CC=C1)OCC)F.C(C)OC=1C=C(C=CC1)C1=CC(=C(C(=C1)F)NC1=C(C(=O)O)C=C(C=N1)C)F Chemical compound C1(CC1)C=1C=NC(=C(C(=O)O)C1)NC1=C(C=C(C=C1F)C1=CC(=CC=C1)OCC)F.C(C)OC=1C=C(C=CC1)C1=CC(=C(C(=C1)F)NC1=C(C(=O)O)C=C(C=N1)C)F UKFJCCOIDYIESK-UHFFFAOYSA-N 0.000 claims 1
- BUYUGUABRGPIGI-UHFFFAOYSA-N CC1=C(C=CC(=C1)NC1=C(C(=O)O)C=CC=N1)C1=CC(=CC=C1)OC(F)(F)F.FC1=C(C=CC=C1OC)C1=CC(=C(C=C1)NC1=C(C(=O)O)C=CC=N1)F.C(C)OC=1C=C(C=CC1)C1=C(C=C(C(=C1)F)NC1=C(C(=O)O)C=CC=N1)F Chemical compound CC1=C(C=CC(=C1)NC1=C(C(=O)O)C=CC=N1)C1=CC(=CC=C1)OC(F)(F)F.FC1=C(C=CC=C1OC)C1=CC(=C(C=C1)NC1=C(C(=O)O)C=CC=N1)F.C(C)OC=1C=C(C=CC1)C1=C(C=C(C(=C1)F)NC1=C(C(=O)O)C=CC=N1)F BUYUGUABRGPIGI-UHFFFAOYSA-N 0.000 claims 1
- CZQRELPNFXSSNC-UHFFFAOYSA-N CC=1C=C(C=CC1NC1=C(C(=O)O)C=CC=N1)C1=CC(=CC=C1)OC(F)(F)F.ClC=1C=C(C=CC1NC1=C(C(=O)O)C=CC=N1)C1=CC(=CC=C1)OCC.ClC=1C=C(C=CC1NC1=C(C(=O)O)C=CC=N1)C1=CC(=CC=C1)OC(F)(F)F Chemical compound CC=1C=C(C=CC1NC1=C(C(=O)O)C=CC=N1)C1=CC(=CC=C1)OC(F)(F)F.ClC=1C=C(C=CC1NC1=C(C(=O)O)C=CC=N1)C1=CC(=CC=C1)OCC.ClC=1C=C(C=CC1NC1=C(C(=O)O)C=CC=N1)C1=CC(=CC=C1)OC(F)(F)F CZQRELPNFXSSNC-UHFFFAOYSA-N 0.000 claims 1
- 229940124292 CD20 monoclonal antibody Drugs 0.000 claims 1
- PCLITLDOTJTVDJ-UHFFFAOYSA-N Chlormethiazole Chemical compound CC=1N=CSC=1CCCl PCLITLDOTJTVDJ-UHFFFAOYSA-N 0.000 claims 1
- ZJHUDRCXYPHTHG-UHFFFAOYSA-N ClC=1C=NC(=C(C(=O)O)C1)NC1=C(C=C(C=C1F)C1=C(C=CC=C1)Cl)F.ClC=1C=NC(=C(C(=O)O)C1)NC1=C(C=C(C=C1F)C1=CC=CC=C1)F.ClC1=C(C=CC=C1)C1=C(C(=C(C(=C1)F)NC1=C(C(=O)O)C=CC=N1)F)C Chemical compound ClC=1C=NC(=C(C(=O)O)C1)NC1=C(C=C(C=C1F)C1=C(C=CC=C1)Cl)F.ClC=1C=NC(=C(C(=O)O)C1)NC1=C(C=C(C=C1F)C1=CC=CC=C1)F.ClC1=C(C=CC=C1)C1=C(C(=C(C(=C1)F)NC1=C(C(=O)O)C=CC=N1)F)C ZJHUDRCXYPHTHG-UHFFFAOYSA-N 0.000 claims 1
- 229930105110 Cyclosporin A Natural products 0.000 claims 1
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims 1
- 108010036949 Cyclosporine Proteins 0.000 claims 1
- 108010052167 Dihydroorotate Dehydrogenase Proteins 0.000 claims 1
- 102100032823 Dihydroorotate dehydrogenase (quinone), mitochondrial Human genes 0.000 claims 1
- 108010008165 Etanercept Proteins 0.000 claims 1
- WBGTWMHBAYCTFN-UHFFFAOYSA-N FC=1C(=C(C=C(C1NC1=C(C(=O)O)C=CC=N1)F)C1=CC(=CC=C1)OC)C.ClC1=C(C=CC=C1)C1=CC(=C(C(=C1)F)NC1=C(C(=O)O)C=C(C=N1)C1CC1)F Chemical compound FC=1C(=C(C=C(C1NC1=C(C(=O)O)C=CC=N1)F)C1=CC(=CC=C1)OC)C.ClC1=C(C=CC=C1)C1=CC(=C(C(=C1)F)NC1=C(C(=O)O)C=C(C=N1)C1CC1)F WBGTWMHBAYCTFN-UHFFFAOYSA-N 0.000 claims 1
- UURNJCOUGYTVBS-UHFFFAOYSA-N FC=1C(=CC(=C(C1)C1=CC(=CC=C1)OC)C)NC1=C(C(=O)O)C=C(C=N1)C.C1(CC1)C=1C=NC(=C(C(=O)O)C1)NC1=CC(=C(C=C1F)C1=CC(=CC=C1)OCC)F Chemical compound FC=1C(=CC(=C(C1)C1=CC(=CC=C1)OC)C)NC1=C(C(=O)O)C=C(C=N1)C.C1(CC1)C=1C=NC(=C(C(=O)O)C1)NC1=CC(=C(C=C1F)C1=CC(=CC=C1)OCC)F UURNJCOUGYTVBS-UHFFFAOYSA-N 0.000 claims 1
- DUAUHUHEPZOEBH-UHFFFAOYSA-N FC=1C=C(C=C(C1NC1=C(C(=O)O)C=C(C=N1)C)F)C1=CC(=CC=C1)OC.C1(CC1)C=1C=NC(=C(C(=O)O)C1)NC1=C(C=C(C=C1)C1=CC(=CC=C1)OC)F Chemical compound FC=1C=C(C=C(C1NC1=C(C(=O)O)C=C(C=N1)C)F)C1=CC(=CC=C1)OC.C1(CC1)C=1C=NC(=C(C(=O)O)C1)NC1=C(C=C(C=C1)C1=CC(=CC=C1)OC)F DUAUHUHEPZOEBH-UHFFFAOYSA-N 0.000 claims 1
- SVJUJOOCJUBPRQ-UHFFFAOYSA-N FC=1C=C(C=C(C1NC1=C(C(=O)O)C=CC=N1)F)C1=CC(=CC=C1)O.FC=1C=C(C=CC1NC1=C(C(=O)O)C=C(C=N1)C)C1=CC(=CC=C1)OC.FC1=C(C=C(C=C1)OC(C)C)C1=CC(=C(C=C1)NC1=C(C(=O)O)C=CC=N1)F Chemical compound FC=1C=C(C=C(C1NC1=C(C(=O)O)C=CC=N1)F)C1=CC(=CC=C1)O.FC=1C=C(C=CC1NC1=C(C(=O)O)C=C(C=N1)C)C1=CC(=CC=C1)OC.FC1=C(C=C(C=C1)OC(C)C)C1=CC(=C(C=C1)NC1=C(C(=O)O)C=CC=N1)F SVJUJOOCJUBPRQ-UHFFFAOYSA-N 0.000 claims 1
- 206010072579 Granulomatosis with polyangiitis Diseases 0.000 claims 1
- 101150006655 INS gene Proteins 0.000 claims 1
- ANMATWQYLIFGOK-UHFFFAOYSA-N Iguratimod Chemical compound CS(=O)(=O)NC1=CC=2OC=C(NC=O)C(=O)C=2C=C1OC1=CC=CC=C1 ANMATWQYLIFGOK-UHFFFAOYSA-N 0.000 claims 1
- 108050006617 Interleukin-1 receptor Proteins 0.000 claims 1
- 102000019223 Interleukin-1 receptor Human genes 0.000 claims 1
- 102000051628 Interleukin-1 receptor antagonist Human genes 0.000 claims 1
- 108700021006 Interleukin-1 receptor antagonist Proteins 0.000 claims 1
- UETNIIAIRMUTSM-UHFFFAOYSA-N Jacareubin Natural products CC1(C)OC2=CC3Oc4c(O)c(O)ccc4C(=O)C3C(=C2C=C1)O UETNIIAIRMUTSM-UHFFFAOYSA-N 0.000 claims 1
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims 1
- 239000012826 P38 inhibitor Substances 0.000 claims 1
- 108010027220 PEGylated soluble tumor necrosis factor receptor I Proteins 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 108700042805 TRU-015 Proteins 0.000 claims 1
- QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 claims 1
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims 1
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims 1
- VJDNZZNMNFGABO-UHFFFAOYSA-N [Li].FC=1C=C(C=C(C1NC1=C(C(=O)O)C=CC=N1)F)C1=CC(=CC=C1)OC Chemical compound [Li].FC=1C=C(C=C(C1NC1=C(C(=O)O)C=CC=N1)F)C1=CC(=CC=C1)OC VJDNZZNMNFGABO-UHFFFAOYSA-N 0.000 claims 1
- 230000004913 activation Effects 0.000 claims 1
- 229960002964 adalimumab Drugs 0.000 claims 1
- 229960003896 aminopterin Drugs 0.000 claims 1
- 229960004238 anakinra Drugs 0.000 claims 1
- 239000005557 antagonist Substances 0.000 claims 1
- 229940046731 calcineurin inhibitors Drugs 0.000 claims 1
- 229960003115 certolizumab pegol Drugs 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229960004414 clomethiazole Drugs 0.000 claims 1
- MVCOAUNKQVWQHZ-UHFFFAOYSA-N doramapimod Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCCN3CCOCC3)=CC=2)=CC(C(C)(C)C)=N1 MVCOAUNKQVWQHZ-UHFFFAOYSA-N 0.000 claims 1
- 229950005521 doramapimod Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229960000403 etanercept Drugs 0.000 claims 1
- 230000014509 gene expression Effects 0.000 claims 1
- 229960001743 golimumab Drugs 0.000 claims 1
- 229950003909 iguratimod Drugs 0.000 claims 1
- 229960000598 infliximab Drugs 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 229950007278 lenercept Drugs 0.000 claims 1
- 229960000485 methotrexate Drugs 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 229950005751 ocrelizumab Drugs 0.000 claims 1
- 229960002450 ofatumumab Drugs 0.000 claims 1
- 229950010444 onercept Drugs 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 229950000867 pegsunercept Drugs 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 239000002464 receptor antagonist Substances 0.000 claims 1
- 229940044551 receptor antagonist Drugs 0.000 claims 1
- 108010003189 recombinant human tumor necrosis factor-binding protein-1 Proteins 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 229960004641 rituximab Drugs 0.000 claims 1
- 201000000306 sarcoidosis Diseases 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- NCEXYHBECQHGNR-QZQOTICOSA-N sulfasalazine Chemical compound C1=C(O)C(C(=O)O)=CC(\N=N\C=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-QZQOTICOSA-N 0.000 claims 1
- 229960001940 sulfasalazine Drugs 0.000 claims 1
- NCEXYHBECQHGNR-UHFFFAOYSA-N sulfasalazine Natural products C1=C(O)C(C(=O)O)=CC(N=NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-UHFFFAOYSA-N 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- 229960001967 tacrolimus Drugs 0.000 claims 1
- QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 claims 1
- ZMELOYOKMZBMRB-DLBZAZTESA-N talmapimod Chemical compound C([C@@H](C)N(C[C@@H]1C)C(=O)C=2C(=CC=3N(C)C=C(C=3C=2)C(=O)C(=O)N(C)C)Cl)N1CC1=CC=C(F)C=C1 ZMELOYOKMZBMRB-DLBZAZTESA-N 0.000 claims 1
- NGOCTERTZUXBOM-UHFFFAOYSA-K trilithium 3-[2-fluoro-4-(3-methoxyphenyl)anilino]pyridine-4-carboxylate 3-[4-(3-methoxyphenyl)-2-(trifluoromethoxy)anilino]pyridine-4-carboxylate pyridine-4-carboxylate Chemical compound [Li+].COC=1C=C(C=CC1)C1=CC(=C(C=C1)NC1=C(C(=O)[O-])C=CN=C1)OC(F)(F)F.[Li+].FC=1C=C(C=CC1NC1=C(C(=O)[O-])C=CN=C1)C1=CC(=CC=C1)OC.[Li+].C(C1=CC=NC=C1)(=O)[O-] NGOCTERTZUXBOM-UHFFFAOYSA-K 0.000 claims 1
- 229960005289 voclosporin Drugs 0.000 claims 1
- 108010057559 voclosporin Proteins 0.000 claims 1
- BICRTLVBTLFLRD-PTWUADNWSA-N voclosporin Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C=C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O BICRTLVBTLFLRD-PTWUADNWSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/465—Nicotine; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Dermatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES200603250A ES2319596B1 (es) | 2006-12-22 | 2006-12-22 | Nuevos derivados de los acidos amino-nicotinico y amino-isonicotinico. |
ES200701086A ES2327372B1 (es) | 2007-04-23 | 2007-04-23 | Nuevos derivados de los acidos amino-nicotinico y amino-isonicotinico. |
PCT/EP2007/011401 WO2008077639A1 (en) | 2006-12-22 | 2007-12-21 | Amino nicotinic and isonicotinic acid derivatives as dhodh inhibitors |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20120697T1 true HRP20120697T1 (hr) | 2012-09-30 |
Family
ID=39319647
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HRP20120697TT HRP20120697T1 (hr) | 2006-12-22 | 2012-09-04 | Derivati aminonikotinske i izonikotinske kiseline kao inhibitori dihidroorotat dehidrogenaze (dhodh) |
Country Status (32)
Country | Link |
---|---|
US (2) | US8258308B2 (pt) |
EP (1) | EP2121614B1 (pt) |
JP (1) | JP5318776B2 (pt) |
KR (1) | KR101435233B1 (pt) |
CN (1) | CN101589025B (pt) |
AR (1) | AR064444A1 (pt) |
AU (1) | AU2007338321B2 (pt) |
BR (1) | BRPI0717697B1 (pt) |
CA (1) | CA2674512C (pt) |
CL (1) | CL2007003666A1 (pt) |
CY (1) | CY1113687T1 (pt) |
DK (1) | DK2121614T3 (pt) |
EC (1) | ECSP099395A (pt) |
ES (2) | ES2319596B1 (pt) |
HK (1) | HK1133014A1 (pt) |
HR (1) | HRP20120697T1 (pt) |
IL (1) | IL199188A (pt) |
ME (1) | ME01475B (pt) |
MX (1) | MX2009006408A (pt) |
MY (1) | MY153393A (pt) |
NO (1) | NO341991B1 (pt) |
NZ (1) | NZ577017A (pt) |
PE (1) | PE20081846A1 (pt) |
PL (1) | PL2121614T3 (pt) |
PT (1) | PT2121614E (pt) |
RS (1) | RS52514B (pt) |
RU (1) | RU2469024C2 (pt) |
SI (1) | SI2121614T1 (pt) |
TW (1) | TWI405572B (pt) |
UY (1) | UY30794A1 (pt) |
WO (1) | WO2008077639A1 (pt) |
ZA (1) | ZA200903335B (pt) |
Families Citing this family (70)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7407955B2 (en) | 2002-08-21 | 2008-08-05 | Boehringer Ingelheim Pharma Gmbh & Co., Kg | 8-[3-amino-piperidin-1-yl]-xanthines, the preparation thereof and their use as pharmaceutical compositions |
CN102838599A (zh) | 2006-05-04 | 2012-12-26 | 贝林格尔.英格海姆国际有限公司 | 多晶型 |
PE20080251A1 (es) | 2006-05-04 | 2008-04-25 | Boehringer Ingelheim Int | Usos de inhibidores de dpp iv |
EP1852108A1 (en) | 2006-05-04 | 2007-11-07 | Boehringer Ingelheim Pharma GmbH & Co.KG | DPP IV inhibitor formulations |
ES2319596B1 (es) | 2006-12-22 | 2010-02-08 | Laboratorios Almirall S.A. | Nuevos derivados de los acidos amino-nicotinico y amino-isonicotinico. |
ES2327372B1 (es) * | 2007-04-23 | 2010-08-24 | Laboratorios Almirall S.A. | Nuevos derivados de los acidos amino-nicotinico y amino-isonicotinico. |
UY31272A1 (es) * | 2007-08-10 | 2009-01-30 | Almirall Lab | Nuevos derivados de ácido azabifenilaminobenzoico |
AR071175A1 (es) | 2008-04-03 | 2010-06-02 | Boehringer Ingelheim Int | Composicion farmaceutica que comprende un inhibidor de la dipeptidil-peptidasa-4 (dpp4) y un farmaco acompanante |
EP2135610A1 (en) * | 2008-06-20 | 2009-12-23 | Laboratorios Almirall, S.A. | Combination comprising DHODH inhibitors and methotrexate |
KR20200118243A (ko) | 2008-08-06 | 2020-10-14 | 베링거 인겔하임 인터내셔날 게엠베하 | 메트포르민 요법이 부적합한 환자에서의 당뇨병 치료 |
US20200155558A1 (en) | 2018-11-20 | 2020-05-21 | Boehringer Ingelheim International Gmbh | Treatment for diabetes in patients with insufficient glycemic control despite therapy with an oral antidiabetic drug |
US20120028985A1 (en) * | 2008-11-07 | 2012-02-02 | 4Sc Ag | Combinational therapy for treating autoimmune disease |
EP2196465A1 (en) | 2008-12-15 | 2010-06-16 | Almirall, S.A. | (3-oxo)pyridazin-4-ylurea derivatives as PDE4 inhibitors |
EP2226323A1 (en) | 2009-02-27 | 2010-09-08 | Almirall, S.A. | New tetrahydropyrazolo[3,4-c]isoquinolin-5-amine derivatives |
EP2228367A1 (en) * | 2009-03-13 | 2010-09-15 | Almirall, S.A. | Addition salts of amines containing hydroxyl and/or carboxylic groups with amino nicotinic acid derivatives as DHODH inhibitors |
EP2239256A1 (en) * | 2009-03-13 | 2010-10-13 | Almirall, S.A. | Sodium salt of 5-cyclopropyl-2-{[2-(2,6-difluorophenyl)pyrimidin-5-yl]amino}benzoic acid as DHODH inhibitor |
TWI530286B (zh) | 2009-05-04 | 2016-04-21 | 帕納特斯製藥格斯有限公司 | 作為抑制病毒化合物之抗發炎劑 |
EP2314577A1 (en) * | 2009-10-16 | 2011-04-27 | Almirall, S.A. | Process for manufacturing 2-[(3,5-difluoro-3'-methoxy-1,1'-biphenyl-4-yl)amino]nicotinic acid |
JP2013512229A (ja) | 2009-11-27 | 2013-04-11 | 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 | 遺伝子型が同定された糖尿病患者のリナグリプチン等のddp−iv阻害薬による治療 |
EP2338888A1 (en) | 2009-12-24 | 2011-06-29 | Almirall, S.A. | Imidazopyridine derivatives as JAK inhibitors |
EP2360158A1 (en) | 2010-02-18 | 2011-08-24 | Almirall, S.A. | Pyrazole derivatives as jak inhibitors |
UY33213A (es) | 2010-02-18 | 2011-09-30 | Almirall Sa | Derivados de pirazol como inhibidores de jak |
EP2380890A1 (en) | 2010-04-23 | 2011-10-26 | Almirall, S.A. | New 7,8-dihydro-1,6-naphthyridin-5(6h)-one-derivatives as PDE4 inhibitors |
US8686048B2 (en) | 2010-05-06 | 2014-04-01 | Rhizen Pharmaceuticals Sa | Immunomodulator and anti-inflammatory compounds |
EP2394998A1 (en) | 2010-05-31 | 2011-12-14 | Almirall, S.A. | 3-(5-Amino-6-oxo-1,6-dihydropyridazin-3-yl)-biphenyl derivatives as PDE4 inhibitors |
EP2397482A1 (en) | 2010-06-15 | 2011-12-21 | Almirall, S.A. | Heteroaryl imidazolone derivatives as jak inhibitors |
EP2441755A1 (en) | 2010-09-30 | 2012-04-18 | Almirall, S.A. | Pyridine- and isoquinoline-derivatives as Syk and JAK kinase inhibitors |
EP2444088A1 (en) | 2010-10-22 | 2012-04-25 | Almirall, S.A. | Amino derivatives for the treatment of proliferative skin disorders |
EP2444086A1 (en) | 2010-10-22 | 2012-04-25 | Almirall, S.A. | Combinations comprising DHODH inhibitors and COX inhibitors |
AR083878A1 (es) | 2010-11-15 | 2013-03-27 | Boehringer Ingelheim Int | Terapia antidiabetica vasoprotectora y cardioprotectora, linagliptina, metodo de tratamiento |
EP2455080A1 (en) | 2010-11-23 | 2012-05-23 | Almirall, S.A. | S1P1 receptor agonists for use in the treatment of multiple sclerosis |
EP2455081A1 (en) | 2010-11-23 | 2012-05-23 | Almirall, S.A. | S1P1 receptor agonists for use in the treatment of crohn's disease |
EP2457900A1 (en) | 2010-11-25 | 2012-05-30 | Almirall, S.A. | New pyrazole derivatives having CRTh2 antagonistic behaviour |
EP2463289A1 (en) | 2010-11-26 | 2012-06-13 | Almirall, S.A. | Imidazo[1,2-b]pyridazine derivatives as JAK inhibitors |
US10016402B2 (en) * | 2011-02-08 | 2018-07-10 | Children's Medical Center Corporation | Methods for treatment of melanoma |
EP2672963A4 (en) | 2011-02-08 | 2015-06-24 | Childrens Medical Center | METHOD FOR THE TREATMENT OF MELANOMA |
EP2489663A1 (en) | 2011-02-16 | 2012-08-22 | Almirall, S.A. | Compounds as syk kinase inhibitors |
EP2518070A1 (en) | 2011-04-29 | 2012-10-31 | Almirall, S.A. | Pyrrolotriazinone derivatives as PI3K inhibitors |
EP2518071A1 (en) | 2011-04-29 | 2012-10-31 | Almirall, S.A. | Imidazopyridine derivatives as PI3K inhibitors |
EP2527344A1 (en) | 2011-05-25 | 2012-11-28 | Almirall, S.A. | Pyridin-2(1H)-one derivatives useful as medicaments for the treatment of myeloproliferative disorders, transplant rejection, immune-mediated and inflammatory diseases |
EP2526945A1 (en) | 2011-05-25 | 2012-11-28 | Almirall, S.A. | New CRTH2 Antagonists |
EP2548876A1 (en) | 2011-07-18 | 2013-01-23 | Almirall, S.A. | New CRTh2 antagonists |
EP2548863A1 (en) | 2011-07-18 | 2013-01-23 | Almirall, S.A. | New CRTh2 antagonists. |
EP2554544A1 (en) | 2011-08-01 | 2013-02-06 | Almirall, S.A. | Pyridin-2(1h)-one derivatives as jak inhibitors |
EP2594271A1 (en) | 2011-11-21 | 2013-05-22 | Almirall, S.A. | 2-[(3,5-difluoro-3'-methoxy-1,1'-biphenyl-4-yl)amino]nicotinic acid for the treatment of psoriasis. |
WO2013171167A1 (en) | 2012-05-14 | 2013-11-21 | Boehringer Ingelheim International Gmbh | A xanthine derivative as dpp -4 inhibitor for use in the treatment of podocytes related disorders and/or nephrotic syndrome |
WO2014060431A1 (en) | 2012-10-16 | 2014-04-24 | Almirall, S.A. | Pyrrolotriazinone derivatives as pi3k inhibitors |
BR112015009777A2 (pt) * | 2012-10-31 | 2017-07-11 | Fujifilm Corp | derivado de amina ou sal do mesmo |
TW201446767A (zh) | 2013-02-15 | 2014-12-16 | Almirall Sa | 作為磷脂肌醇3-激酶抑製劑之吡咯並三嗪衍生物 |
KR20160079123A (ko) | 2013-11-22 | 2016-07-05 | 젠자임 코포레이션 | 신경변성 질병을 치료하기 위한 신규한 방법 |
CA2944570A1 (en) | 2014-04-11 | 2015-10-15 | Panoptes Pharma Gmbh | Anti-inflammatory agents as virostatic compounds |
WO2015169944A1 (en) * | 2014-05-08 | 2015-11-12 | Panoptes Pharma Ges.M.B.H. | Compounds for treating ophthalmic diseases and disorders |
WO2016200778A1 (en) * | 2015-06-08 | 2016-12-15 | Children's Medical Center Corporation | Methods for treatment of melanoma |
WO2016202800A1 (en) | 2015-06-16 | 2016-12-22 | Almirall, S.A. | Pyrrolotriazinone derivatives as pi3k inhibitors |
AU2017276758A1 (en) | 2016-06-10 | 2018-11-08 | Boehringer Ingelheim International Gmbh | Combinations of Linagliptin and metformin |
WO2018136009A1 (en) | 2017-01-20 | 2018-07-26 | Aslan Pharmaceuticals Pte Ltd | Combination therapy |
WO2018136010A1 (en) | 2017-01-20 | 2018-07-26 | Aslan Pharmaceuticals Pte Ltd | Combination therapy |
WO2018157843A1 (zh) * | 2017-03-02 | 2018-09-07 | 中国科学院上海药物研究所 | 2-(取代苯杂基)芳香甲酸类fto抑制剂,其制备方法及其应用 |
WO2018160138A1 (en) | 2017-03-02 | 2018-09-07 | Aslan Pharmaceuticals Pte Ltd | Dhodh inhibitor for treating haematological cancer |
US11311548B2 (en) | 2017-03-02 | 2022-04-26 | Aslan Pharmaceuticals Pte. Ltd. | Cancer therapy |
JP6978251B2 (ja) * | 2017-03-03 | 2021-12-08 | アスラン ファーマシューティカルズ ピーティーイー リミテッド | がん治療 |
WO2018222134A1 (en) | 2017-06-02 | 2018-12-06 | Aslan Pharmaceuticals Pte Ltd | Cancer therapy |
WO2018222135A1 (en) | 2017-06-02 | 2018-12-06 | Aslan Pharmaceuticals Pte Ltd | Cancer therapy |
EP3858361A4 (en) | 2018-09-28 | 2021-12-01 | FUJIFILM Corporation | ANTITUMOR AGENT CONTAINING CYTARABINE, ANTITUMOR ACTIVATOR USED IN COMBINATION WITH CYTARABINE, ANTITUMOR KIT, AND ANTITUMOR AGENT USED IN COMBINATION WITH CYTARABINE |
JP7409670B2 (ja) | 2018-12-21 | 2024-01-09 | 国立大学法人北海道大学 | 多能性幹細胞を除去するための組成物、及び多能性幹細胞の除去方法 |
EP3750892A1 (en) | 2019-06-14 | 2020-12-16 | Yerevan State University | Novel 5-cyclopropyl-furo[3,4-c]pyridine-3,4(1h,5h)-dione 1,1' substituted derivatives and their uses |
WO2021085582A1 (ja) * | 2019-10-31 | 2021-05-06 | 富士フイルム株式会社 | ピラジン誘導体またはその塩およびその利用 |
JPWO2022025174A1 (pt) * | 2020-07-30 | 2022-02-03 | ||
US20230390276A1 (en) * | 2020-10-15 | 2023-12-07 | Aslan Pharmaceuticals Pte. Ltd. | Treatment of autoimmune diseases with a dihydroorotate hehydrogenase (dhodh) inhibitor |
US20230242558A1 (en) * | 2022-01-31 | 2023-08-03 | New Frontier Bio, Inc. | Nicotinate and nicotinamide riboside-based compounds and derivatives thereof |
Family Cites Families (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US529490A (en) * | 1894-11-20 | hegg-em | ||
EP0008532B1 (en) * | 1978-08-22 | 1983-07-20 | Sumitomo Chemical Company, Limited | Synthesis of amines |
JPH05331163A (ja) * | 1991-03-26 | 1993-12-14 | Kumiai Chem Ind Co Ltd | ピリジン誘導体及び除草剤 |
CA2148928C (en) * | 1993-10-01 | 2005-10-18 | Jurg Zimmermann | Pharmacologically active pyridine derivatives and processes for the preparation thereof |
PL182198B1 (en) | 1995-06-21 | 2001-11-30 | Asta Medica Ag | Pharmaceutic powder holding container with integrated measuring device and powdered |
DE19547648A1 (de) | 1995-12-20 | 1997-06-26 | Hoechst Ag | Zubereitung, enthaltend High Density Lipoproteine und Crotonsäureamidderivate |
DE19610955A1 (de) | 1996-03-20 | 1997-09-25 | Hoechst Ag | Kombinationspräparat, enthaltend 5-Methylisoxazol-4-carbonsäure-(4-trifluormethyl)- anilid und N-(4-Trifluormethylphenyl)-2-cyan-3- hydroxycrotonsäureamid |
GB9804343D0 (en) | 1998-02-27 | 1998-04-22 | Univ Cardiff | Chemical compounds |
PL352430A1 (en) * | 1999-06-10 | 2003-08-25 | Warner Lambert Co | Method of inhibiting agreggation of amyloid proteins and visualising amyloid deposits |
EP1381356B1 (en) | 2001-04-05 | 2008-05-28 | Aventis Pharmaceuticals Inc. | Use of (z)-2-cyano-3-hydroxy-but-2-enoic acid-(4'-trifluoromethylphenyl)-amide for treating multiple sclerosis |
PE20030120A1 (es) | 2001-06-19 | 2003-02-12 | Merck & Co Inc | Sal amina de un antagonista de receptor de integrin |
DE10129703A1 (de) | 2001-06-22 | 2003-01-02 | Sofotec Gmbh & Co Kg | Zerstäubungssystem für eine Pulvermischung und Verfahren für Trockenpulverinhalatoren |
WO2003006424A1 (en) * | 2001-07-10 | 2003-01-23 | 4Sc Ag | Novel compounds as anti-inflammatory, immunomodulatory and anti-proliferatory agents |
DE10202940A1 (de) | 2002-01-24 | 2003-07-31 | Sofotec Gmbh & Co Kg | Patrone für einen Pulverinhalator |
US7258118B2 (en) | 2002-01-24 | 2007-08-21 | Sofotec Gmbh & Co, Kg | Pharmaceutical powder cartridge, and inhaler equipped with same |
PE20040844A1 (es) | 2002-11-26 | 2004-12-30 | Novartis Ag | Acidos fenilaceticos y derivados como inhibidores de la cox-2 |
WO2004056747A1 (en) * | 2002-12-23 | 2004-07-08 | 4Sc Ag | Dhodh-inhibitors and method for their identification |
WO2004056746A1 (en) | 2002-12-23 | 2004-07-08 | 4Sc Ag | Cycloalkene dicarboxylic acid compounds as anti-inflammatory, immunomodulatory and anti-proliferatory agents |
SE0400234D0 (sv) | 2004-02-06 | 2004-02-06 | Active Biotech Ab | New compounds, methods for their preparation and use thereof |
US20070219224A1 (en) | 2004-05-21 | 2007-09-20 | Uab Research Foundation, The | Compositions and Methods Relating to Pyrimidine Synthesis Inhibitors |
WO2006022442A1 (ja) * | 2004-08-24 | 2006-03-02 | Santen Pharmaceutical Co., Ltd. | ジヒドロオロテートデヒドロゲナーゼ阻害活性を有する新規複素環アミド誘導体 |
KR20070065888A (ko) | 2004-10-19 | 2007-06-25 | 아벤티스 파마슈티칼스 인크. | 염증성 장질환을 치료하기 위한(z)-2-시아노-3-하이드록시-부트-2-엔산-(4'-트리플루오로메틸페닐)-아미드의 용도 |
PT1802579E (pt) * | 2004-10-20 | 2014-02-17 | Merck Serono Sa | Derivados da 3-arilaminopiridina |
ES2265276B1 (es) | 2005-05-20 | 2008-02-01 | Laboratorios Almirall S.A. | Derivados de 4-(2-amino-1-hidroxietil)fenol como agonistas del receptor beta2 adrenergico. |
ES2319596B1 (es) | 2006-12-22 | 2010-02-08 | Laboratorios Almirall S.A. | Nuevos derivados de los acidos amino-nicotinico y amino-isonicotinico. |
KR20090110931A (ko) | 2007-02-06 | 2009-10-23 | 첼시 쎄라퓨틱스, 인코포레이티드 | 신규한 화합물, 이의 제조방법 및 이의 용도 |
UY31272A1 (es) | 2007-08-10 | 2009-01-30 | Almirall Lab | Nuevos derivados de ácido azabifenilaminobenzoico |
EP2135610A1 (en) | 2008-06-20 | 2009-12-23 | Laboratorios Almirall, S.A. | Combination comprising DHODH inhibitors and methotrexate |
EP2210615A1 (en) | 2009-01-21 | 2010-07-28 | Almirall, S.A. | Combinations comprising methotrexate and DHODH inhibitors |
EP2230232A1 (en) | 2009-03-13 | 2010-09-22 | Almirall, S.A. | Addition salts of tromethamine with azabiphenylaminobenzoic acid derivatives as DHODH inhibitors |
EP2228367A1 (en) | 2009-03-13 | 2010-09-15 | Almirall, S.A. | Addition salts of amines containing hydroxyl and/or carboxylic groups with amino nicotinic acid derivatives as DHODH inhibitors |
EP2239256A1 (en) | 2009-03-13 | 2010-10-13 | Almirall, S.A. | Sodium salt of 5-cyclopropyl-2-{[2-(2,6-difluorophenyl)pyrimidin-5-yl]amino}benzoic acid as DHODH inhibitor |
EP2314577A1 (en) | 2009-10-16 | 2011-04-27 | Almirall, S.A. | Process for manufacturing 2-[(3,5-difluoro-3'-methoxy-1,1'-biphenyl-4-yl)amino]nicotinic acid |
-
2006
- 2006-12-22 ES ES200603250A patent/ES2319596B1/es not_active Withdrawn - After Issue
-
2007
- 2007-12-13 UY UY30794A patent/UY30794A1/es active IP Right Grant
- 2007-12-17 TW TW096148215A patent/TWI405572B/zh active
- 2007-12-17 CL CL200703666A patent/CL2007003666A1/es unknown
- 2007-12-19 AR ARP070105721A patent/AR064444A1/es active IP Right Grant
- 2007-12-21 AU AU2007338321A patent/AU2007338321B2/en active Active
- 2007-12-21 MY MYPI20092607A patent/MY153393A/en unknown
- 2007-12-21 RU RU2009127847/04A patent/RU2469024C2/ru active
- 2007-12-21 KR KR1020097012714A patent/KR101435233B1/ko active IP Right Grant
- 2007-12-21 ES ES07866261T patent/ES2389785T3/es active Active
- 2007-12-21 RS RS20120388A patent/RS52514B/en unknown
- 2007-12-21 JP JP2009541921A patent/JP5318776B2/ja active Active
- 2007-12-21 SI SI200731012T patent/SI2121614T1/sl unknown
- 2007-12-21 DK DK07866261.6T patent/DK2121614T3/da active
- 2007-12-21 MX MX2009006408A patent/MX2009006408A/es active IP Right Grant
- 2007-12-21 NZ NZ577017A patent/NZ577017A/en unknown
- 2007-12-21 CA CA2674512A patent/CA2674512C/en active Active
- 2007-12-21 EP EP07866261A patent/EP2121614B1/en active Active
- 2007-12-21 BR BRPI0717697-0A patent/BRPI0717697B1/pt active IP Right Grant
- 2007-12-21 WO PCT/EP2007/011401 patent/WO2008077639A1/en active Application Filing
- 2007-12-21 PL PL07866261T patent/PL2121614T3/pl unknown
- 2007-12-21 PT PT07866261T patent/PT2121614E/pt unknown
- 2007-12-21 CN CN200780047756XA patent/CN101589025B/zh active Active
- 2007-12-21 US US12/520,237 patent/US8258308B2/en active Active
- 2007-12-21 ME MEP-2012-104A patent/ME01475B/me unknown
-
2008
- 2008-01-02 PE PE2008000062A patent/PE20081846A1/es active IP Right Grant
-
2009
- 2009-05-14 ZA ZA200903333A patent/ZA200903335B/xx unknown
- 2009-06-04 IL IL199188A patent/IL199188A/en active IP Right Grant
- 2009-06-09 EC EC2009009395A patent/ECSP099395A/es unknown
- 2009-06-22 NO NO20092380A patent/NO341991B1/no unknown
- 2009-12-31 HK HK09112354.6A patent/HK1133014A1/xx unknown
-
2012
- 2012-08-06 US US13/567,437 patent/US8691852B2/en active Active
- 2012-09-04 HR HRP20120697TT patent/HRP20120697T1/hr unknown
- 2012-09-04 CY CY20121100791T patent/CY1113687T1/el unknown
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
HRP20120697T1 (hr) | Derivati aminonikotinske i izonikotinske kiseline kao inhibitori dihidroorotat dehidrogenaze (dhodh) | |
AR072174A1 (es) | Combinaciones que comprenden inhibidores de dhodh (dihidroorotato deshidrogenasa) y metotrexato. uso. producto. kit. metodo. | |
RU2481334C2 (ru) | Производные азабифениламинобензойной кислоты в качестве ингибиторов dhodh | |
AR075036A1 (es) | Combinaciones que comprenden metotrexato e inhibidores de dhodh | |
AU2011249546B9 (en) | Novel immunomodulator and anti inflammatory compounds | |
AU2011249546C1 (en) | Novel immunomodulator and anti inflammatory compounds | |
RU2006146985A (ru) | Модуляторы мускариновых рецепторов | |
JP2009518338A (ja) | バニロイドアンタゴニストとしての三置換キナゾリノン誘導体 | |
NZ594492A (en) | Sodium salt of 5-cyclopropyl-2-{ [2-(2,6- difluorophenyl)pyrimidin-5-yl]amino} benzoic acid as dhodh inhibitor | |
Yang et al. | Discovery and lead identification of quinazoline-based BRD4 inhibitors | |
ES2327372B1 (es) | Nuevos derivados de los acidos amino-nicotinico y amino-isonicotinico. | |
Harrington et al. | Research and development of an efficient process for the construction of the 2, 4, 5-substituted pyridines of NK-1 receptor antagonists | |
Singh et al. | Insilico proteomics and genomics studies on thyx of mycobacterium tuberculosis | |
ES2315185B1 (es) | Nuevos derivados del acido azabifenilaminobenzoico. |