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)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Dermatology (AREA)
- Pain & Pain Management (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 (fr) | 2006-12-22 | 2007-12-21 | Dérivés d'acides amino nicotinique et isonicotinique comme inhibiteurs de la dhodh |
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 (fr) |
EP (1) | EP2121614B1 (fr) |
JP (1) | JP5318776B2 (fr) |
KR (1) | KR101435233B1 (fr) |
CN (1) | CN101589025B (fr) |
AR (1) | AR064444A1 (fr) |
AU (1) | AU2007338321B2 (fr) |
BR (1) | BRPI0717697B1 (fr) |
CA (1) | CA2674512C (fr) |
CL (1) | CL2007003666A1 (fr) |
CY (1) | CY1113687T1 (fr) |
DK (1) | DK2121614T3 (fr) |
EC (1) | ECSP099395A (fr) |
ES (2) | ES2319596B1 (fr) |
HK (1) | HK1133014A1 (fr) |
HR (1) | HRP20120697T1 (fr) |
IL (1) | IL199188A (fr) |
ME (1) | ME01475B (fr) |
MX (1) | MX2009006408A (fr) |
MY (1) | MY153393A (fr) |
NO (1) | NO341991B1 (fr) |
NZ (1) | NZ577017A (fr) |
PE (1) | PE20081846A1 (fr) |
PL (1) | PL2121614T3 (fr) |
PT (1) | PT2121614E (fr) |
RS (1) | RS52514B (fr) |
RU (1) | RU2469024C2 (fr) |
SI (1) | SI2121614T1 (fr) |
TW (1) | TWI405572B (fr) |
UY (1) | UY30794A1 (fr) |
WO (1) | WO2008077639A1 (fr) |
ZA (1) | ZA200903335B (fr) |
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 |
PE20110235A1 (es) | 2006-05-04 | 2011-04-14 | Boehringer Ingelheim Int | Combinaciones farmaceuticas que comprenden linagliptina y metmorfina |
CA2810839A1 (fr) | 2006-05-04 | 2007-11-15 | Boehringer Ingelheim International Gmbh | Polymorphes |
EP1852108A1 (fr) | 2006-05-04 | 2007-11-07 | Boehringer Ingelheim Pharma GmbH & Co.KG | Compositions d'inhibiteurs de la DPP IV |
ES2327372B1 (es) * | 2007-04-23 | 2010-08-24 | Laboratorios Almirall S.A. | Nuevos derivados de los acidos amino-nicotinico y amino-isonicotinico. |
ES2319596B1 (es) | 2006-12-22 | 2010-02-08 | 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 |
PE20091730A1 (es) | 2008-04-03 | 2009-12-10 | Boehringer Ingelheim Int | Formulaciones que comprenden un inhibidor de dpp4 |
EP2135610A1 (fr) * | 2008-06-20 | 2009-12-23 | Laboratorios Almirall, S.A. | Combinaison comportant des inhibiteurs DHODH et de la méthotrexate |
BRPI0916997A2 (pt) | 2008-08-06 | 2020-12-15 | Boehringer Ingelheim International Gmbh | Inibidor de dpp-4 e seu uso |
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 |
BRPI0921258A2 (pt) * | 2008-11-07 | 2018-10-23 | 4Sc Ag | terapia combinatória compreendendo inibidor de dhodh e metotrexato para o tratamento de doença autoimune |
EP2196465A1 (fr) | 2008-12-15 | 2010-06-16 | Almirall, S.A. | Dérivés de (3-oxo)pyridazin-4-ylurée comme inhibiteurs de PDE4 |
EP2226323A1 (fr) | 2009-02-27 | 2010-09-08 | Almirall, S.A. | Nouveaux dérivés de tétrahydropyrazolo [3,4-c]isoquinoléine-5-amine |
EP2239256A1 (fr) * | 2009-03-13 | 2010-10-13 | Almirall, S.A. | Sel de sodium de l'acide 5-cyclopropyl-2-{[2-(2,6-difluorophényl)pyrimidin-5-yl]amino}benzoïque en tant qu'inhibiteurs de la DHOD |
EP2228367A1 (fr) | 2009-03-13 | 2010-09-15 | Almirall, S.A. | Sels adjuvants d'amines contenant des groupes hydroxyle et/ou carbonyle avec des dérivés d'acides aminonicotiques en tant qu'inhibiteurs de la DHODH |
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 (fr) * | 2009-10-16 | 2011-04-27 | Almirall, S.A. | Procédé de fabrication de l'acide 2-[(3,5-difluoro-3'-méthoxy-1,1'-biphényl-4-yl)amino]nicotinique |
CN107115530A (zh) | 2009-11-27 | 2017-09-01 | 勃林格殷格翰国际有限公司 | 基因型糖尿病患者利用dpp‑iv抑制剂例如利拉利汀的治疗 |
EP2338888A1 (fr) | 2009-12-24 | 2011-06-29 | Almirall, S.A. | Dérivés d'imidazopyridine en tant qu'inhibiteurs JAK |
EP2360158A1 (fr) | 2010-02-18 | 2011-08-24 | Almirall, S.A. | Dérivés de pyrazole en tant qu'inhibiteurs de JAK |
UY33213A (es) | 2010-02-18 | 2011-09-30 | Almirall Sa | Derivados de pirazol como inhibidores de jak |
EP2380890A1 (fr) | 2010-04-23 | 2011-10-26 | Almirall, S.A. | Nouveaux dérivés de 7,8-dihydro-1,6-naphthyridin-5(6h)-one comme PDE4 inhibiteurs |
US8686048B2 (en) | 2010-05-06 | 2014-04-01 | Rhizen Pharmaceuticals Sa | Immunomodulator and anti-inflammatory compounds |
EP2394998A1 (fr) | 2010-05-31 | 2011-12-14 | Almirall, S.A. | Dérivés de 3-(5-Amino-6-oxo-1,6-dihydropyridazin-3-yl)-biphenyl en tant qu'inhibiteurs de la PDE4 |
EP2397482A1 (fr) | 2010-06-15 | 2011-12-21 | Almirall, S.A. | Dérivés d'imidazolone d'hétéroaryle en tant qu'inhibiteurs de JAK |
EP2441755A1 (fr) | 2010-09-30 | 2012-04-18 | Almirall, S.A. | Dérivés de pyridine et isoquinoline comme inhibiteurs des kinases Syk et JAK |
EP2444088A1 (fr) | 2010-10-22 | 2012-04-25 | Almirall, S.A. | Dérivés amino pour le traitement de troubles prolifératifs de la peau |
EP2444086A1 (fr) | 2010-10-22 | 2012-04-25 | Almirall, S.A. | Combinaisons comportant des inhibiteurs de DHODH et de COX |
US9034883B2 (en) | 2010-11-15 | 2015-05-19 | Boehringer Ingelheim International Gmbh | Vasoprotective and cardioprotective antidiabetic therapy |
EP2455080A1 (fr) | 2010-11-23 | 2012-05-23 | Almirall, S.A. | Agonistes de récepteur S1P1 à utiliser dans le traitement de la sclérose en plaques |
EP2455081A1 (fr) | 2010-11-23 | 2012-05-23 | Almirall, S.A. | Agonistes de récepteur S1P1 à utiliser dans le traitement de la maladie de Crohn |
EP2457900A1 (fr) | 2010-11-25 | 2012-05-30 | Almirall, S.A. | Nouveaux dérivés de pyrazole présentant un comportement antagoniste CRTH2 |
EP2463289A1 (fr) | 2010-11-26 | 2012-06-13 | Almirall, S.A. | Dérivés imidazo[1,2-b]pyridazine en tant qu'inhibiteur JAK |
US10016402B2 (en) | 2011-02-08 | 2018-07-10 | Children's Medical Center Corporation | Methods for treatment of melanoma |
US20140031383A1 (en) | 2011-02-08 | 2014-01-30 | Dana-Farber Cancer Institute, Inc. | Methods for treatment of melanoma |
EP2489663A1 (fr) | 2011-02-16 | 2012-08-22 | Almirall, S.A. | Composés en tant qu'inhibiteurs de la syk kinase |
EP2518070A1 (fr) | 2011-04-29 | 2012-10-31 | Almirall, S.A. | Dérivés de pyrrolotriazinon en tant qu'inhibiteurs PI3K |
EP2518071A1 (fr) | 2011-04-29 | 2012-10-31 | Almirall, S.A. | Dérivés d'imidazopyridine en tant qu'inhibiteurs PI3K |
EP2527344A1 (fr) | 2011-05-25 | 2012-11-28 | Almirall, S.A. | Dérivés de pyridin-2(1h)-one utiles comme médicaments pour le traitement de maladies myeloproliferatives, de rejets de greffe, de maladies a médiation immune et de maladies inflammatoires |
EP2526945A1 (fr) | 2011-05-25 | 2012-11-28 | Almirall, S.A. | Nouveaux antagonistes de CRTH2 |
EP2548876A1 (fr) | 2011-07-18 | 2013-01-23 | Almirall, S.A. | Nouveaux antagonistes de CRTH2 |
EP2548863A1 (fr) | 2011-07-18 | 2013-01-23 | Almirall, S.A. | Nouveaux antagonistes de CRTH2 |
EP2554544A1 (fr) | 2011-08-01 | 2013-02-06 | Almirall, S.A. | Dérivés de pyridin-2(1h)-one en tant qu'inhibiteurs de JAK |
EP2594271A1 (fr) | 2011-11-21 | 2013-05-22 | Almirall, S.A. | Acide 2-[(3,5-difluoro-3'-méthoxy-1,1'-biphényl-4-YL)aminonicotinique pour le traitement du psoriasis |
US20130303462A1 (en) | 2012-05-14 | 2013-11-14 | Boehringer Ingelheim International Gmbh | Use of a dpp-4 inhibitor in podocytes related disorders and/or nephrotic syndrome |
WO2014060431A1 (fr) | 2012-10-16 | 2014-04-24 | Almirall, S.A. | Dérivés de pyrrolotriazinone en tant qu'inhibiteurs des pi3k |
JP6466171B2 (ja) | 2012-10-31 | 2019-02-06 | 富士フイルム富山化学株式会社 | 新規アミン誘導体またはその塩 |
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 |
AU2014352920A1 (en) | 2013-11-22 | 2016-06-23 | Genzyme Corporation | Novel methods for treating neurodegenerative diseases |
KR102265277B1 (ko) | 2014-04-11 | 2021-06-16 | 판옵테스 파르마 게스.엠.베.하. | 바이러스 억제 화합물로서의 항-염증제 |
US11730716B2 (en) | 2014-05-08 | 2023-08-22 | Kiora Pharmaceuticals Gmbh | Compounds for treating ophthalmic diseases and disorders |
WO2016200778A1 (fr) * | 2015-06-08 | 2016-12-15 | Children's Medical Center Corporation | Procédés de traitement de mélanome |
WO2016202800A1 (fr) | 2015-06-16 | 2016-12-22 | Almirall, S.A. | Dérivés de pyrrolotriazinone en tant qu'inhibiteurs de pi3k |
CA3022202A1 (fr) | 2016-06-10 | 2017-12-14 | Boehringer Ingelheim International Gmbh | Combinaisons de linagliptine et de metformine |
WO2018136009A1 (fr) | 2017-01-20 | 2018-07-26 | Aslan Pharmaceuticals Pte Ltd | Polythérapie |
WO2018136010A1 (fr) | 2017-01-20 | 2018-07-26 | Aslan Pharmaceuticals Pte Ltd | Polythérapie |
TW201834649A (zh) | 2017-03-02 | 2018-10-01 | 新加坡商亞獅康私人有限公司 | 癌症療法 |
CN108530310A (zh) * | 2017-03-02 | 2018-09-14 | 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 |
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 |
WO2018222135A1 (fr) | 2017-06-02 | 2018-12-06 | Aslan Pharmaceuticals Pte Ltd | Cancérothérapie |
WO2018222134A1 (fr) | 2017-06-02 | 2018-12-06 | Aslan Pharmaceuticals Pte Ltd | Cancérothérapie |
JP7126556B2 (ja) | 2018-09-28 | 2022-08-26 | 富士フイルム株式会社 | シタラビンを含む抗腫瘍剤、シタラビンと併用される抗腫瘍効果増強剤、抗腫瘍用キット、およびシタラビンと併用される抗腫瘍剤 |
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 (fr) | 2019-06-14 | 2020-12-16 | Yerevan State University | Nouveaux dérivés substitués de 5-cyclopropyl-furo[3,4-c]pyridine-3,4(1h,5h)-dione 1,1' et leurs utilisations |
JP7288074B2 (ja) * | 2019-10-31 | 2023-06-06 | 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 |
CN116056766A (zh) * | 2020-07-30 | 2023-05-02 | 富士胶片株式会社 | 含氮杂环化合物或其盐、其利用以及其中间体 |
US20230390276A1 (en) * | 2020-10-15 | 2023-12-07 | Aslan Pharmaceuticals Pte. Ltd. | Treatment of autoimmune diseases with a dihydroorotate hehydrogenase (dhodh) inhibitor |
WO2023147161A2 (fr) * | 2022-01-31 | 2023-08-03 | New Frontier Bio, Inc. | Composés à base de nicotinate riboside et de nicotinamide riboside et leurs dérivés |
Family Cites Families (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US529490A (en) * | 1894-11-20 | hegg-em | ||
EP0040896B1 (fr) * | 1978-08-22 | 1984-04-25 | Sumitomo Chemical Company, Limited | Synthèse d'amides |
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 |
KR100330553B1 (ko) * | 1993-10-01 | 2002-11-27 | 노파르티스 아게 | 약물학적활성피리딘유도체및그의제조방법 |
CA2378713C (fr) | 1995-06-21 | 2003-08-12 | Asta Medica Aktiengesellschaft | Cartouche de poudre pharmaceutique avec appareil de dosage integre et inhalateur pour medicaments en poudre |
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 |
NZ515621A (en) * | 1999-06-10 | 2004-05-28 | Warner Lambert Co | Medicaments for inhibiting amyloid protein aggregation and methods of imaging amyloid deposits |
EP1935416A3 (fr) | 2001-04-05 | 2008-10-22 | Aventis Pharma Inc | Utilisation de l'acide (Z)-2-cyano-3-hydroxy-but-2-enoïque-(4'-trifluorromethylphenyl)-amide pour traiter la sclérose en plaques |
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 (fr) * | 2001-07-10 | 2003-01-23 | 4Sc Ag | Nouveaux composes utilises comme agents anti-inflammatoires, immunomodulateurs et anti-proliferatoires |
US7258118B2 (en) | 2002-01-24 | 2007-08-21 | Sofotec Gmbh & Co, Kg | Pharmaceutical powder cartridge, and inhaler equipped with same |
DE10202940A1 (de) | 2002-01-24 | 2003-07-31 | Sofotec Gmbh & Co Kg | Patrone für einen Pulverinhalator |
AR042206A1 (es) | 2002-11-26 | 2005-06-15 | Novartis Ag | Acidos fenilaceticos y derivados |
WO2004056746A1 (fr) | 2002-12-23 | 2004-07-08 | 4Sc Ag | Composes d'acide dicarboxylique de cycloalcene servant d'agents anti-inflammatoires, d'immunomodulation et anti-proliferation |
EP1581478A1 (fr) * | 2002-12-23 | 2005-10-05 | 4Sc Ag | Inhibiteurs de l'enzyme dhodh et leur procede d'identification |
SE0400234D0 (sv) | 2004-02-06 | 2004-02-06 | Active Biotech Ab | New compounds, methods for their preparation and use thereof |
CN1993125A (zh) | 2004-05-21 | 2007-07-04 | Uab研究基金会 | 涉及嘧啶合成抑制剂的组合物和方法 |
WO2006022442A1 (fr) * | 2004-08-24 | 2006-03-02 | Santen Pharmaceutical Co., Ltd. | Nouveaux derives d’amides heterocycliques ayant une activite d’inhibition de la dihydroorotate deshydrogenase |
CN101043883A (zh) | 2004-10-19 | 2007-09-26 | 安万特药物公司 | (z)-2-氰基-3-羟基-丁-2-烯酸-(4'-三氟甲基苯基)-酰胺用于治疗炎症性肠病的用途 |
EP1802579B1 (fr) * | 2004-10-20 | 2013-11-20 | Merck Serono SA | Dérivés de 3-arylaminopyridine |
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. |
DE602008006679D1 (de) | 2007-02-06 | 2011-06-16 | Chelsea Therapeutics Inc | Neue verbindungen, verfahren zu deren herstellung und deren verwendung |
UY31272A1 (es) | 2007-08-10 | 2009-01-30 | Almirall Lab | Nuevos derivados de ácido azabifenilaminobenzoico |
EP2135610A1 (fr) | 2008-06-20 | 2009-12-23 | Laboratorios Almirall, S.A. | Combinaison comportant des inhibiteurs DHODH et de la méthotrexate |
EP2210615A1 (fr) | 2009-01-21 | 2010-07-28 | Almirall, S.A. | Combinaisons comportant des inhibiteurs DHODH et de la méthotrexate |
EP2228367A1 (fr) | 2009-03-13 | 2010-09-15 | Almirall, S.A. | Sels adjuvants d'amines contenant des groupes hydroxyle et/ou carbonyle avec des dérivés d'acides aminonicotiques en tant qu'inhibiteurs de la DHODH |
EP2239256A1 (fr) | 2009-03-13 | 2010-10-13 | Almirall, S.A. | Sel de sodium de l'acide 5-cyclopropyl-2-{[2-(2,6-difluorophényl)pyrimidin-5-yl]amino}benzoïque en tant qu'inhibiteurs de la DHOD |
EP2230232A1 (fr) | 2009-03-13 | 2010-09-22 | Almirall, S.A. | Sels adjuvants de trométhamine dotés de dérivés d'acide azabiphénylaminobenzoïque en tant qu'inhibiteurs de la DHOD |
EP2314577A1 (fr) | 2009-10-16 | 2011-04-27 | Almirall, S.A. | Procédé de fabrication de l'acide 2-[(3,5-difluoro-3'-méthoxy-1,1'-biphényl-4-yl)amino]nicotinique |
-
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 CL CL200703666A patent/CL2007003666A1/es unknown
- 2007-12-17 TW TW096148215A patent/TWI405572B/zh active
- 2007-12-19 AR ARP070105721A patent/AR064444A1/es active IP Right Grant
- 2007-12-21 US US12/520,237 patent/US8258308B2/en active Active
- 2007-12-21 RU RU2009127847/04A patent/RU2469024C2/ru active
- 2007-12-21 NZ NZ577017A patent/NZ577017A/en unknown
- 2007-12-21 RS RS20120388A patent/RS52514B/en unknown
- 2007-12-21 AU AU2007338321A patent/AU2007338321B2/en active Active
- 2007-12-21 ES ES07866261T patent/ES2389785T3/es active Active
- 2007-12-21 DK DK07866261.6T patent/DK2121614T3/da active
- 2007-12-21 BR BRPI0717697-0A patent/BRPI0717697B1/pt active IP Right Grant
- 2007-12-21 ME MEP-2012-104A patent/ME01475B/me unknown
- 2007-12-21 SI SI200731012T patent/SI2121614T1/sl unknown
- 2007-12-21 KR KR1020097012714A patent/KR101435233B1/ko active IP Right Grant
- 2007-12-21 JP JP2009541921A patent/JP5318776B2/ja active Active
- 2007-12-21 CN CN200780047756XA patent/CN101589025B/zh active Active
- 2007-12-21 EP EP07866261A patent/EP2121614B1/fr active Active
- 2007-12-21 MY MYPI20092607A patent/MY153393A/en unknown
- 2007-12-21 PT PT07866261T patent/PT2121614E/pt unknown
- 2007-12-21 PL PL07866261T patent/PL2121614T3/pl unknown
- 2007-12-21 MX MX2009006408A patent/MX2009006408A/es active IP Right Grant
- 2007-12-21 WO PCT/EP2007/011401 patent/WO2008077639A1/fr active Application Filing
- 2007-12-21 CA CA2674512A patent/CA2674512C/fr active Active
-
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 CY CY20121100791T patent/CY1113687T1/el unknown
- 2012-09-04 HR HRP20120697TT patent/HRP20120697T1/hr 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. | |
RU2010108261A (ru) | Производные азабифениламинобензойной кислоты в качестве ингибиторов 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 | |
NZ594491A (en) | Addition salts of tromethamine with azabiphenylaminobenzoic acid derivatives as dhodh 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. | |
Balaswamy et al. | Synthesis, Antimicrobial Activity, and Docking Studies of 2-Mercapto Substituted Quinazolin-4 (3 H)-one and Their Derivatives |