SI2850070T1 - Benzo (1,3) dioxin derivatives and their use as LPAR5 antagonists - Google Patents
Benzo (1,3) dioxin derivatives and their use as LPAR5 antagonists Download PDFInfo
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- SI2850070T1 SI2850070T1 SI201330853T SI201330853T SI2850070T1 SI 2850070 T1 SI2850070 T1 SI 2850070T1 SI 201330853 T SI201330853 T SI 201330853T SI 201330853 T SI201330853 T SI 201330853T SI 2850070 T1 SI2850070 T1 SI 2850070T1
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- alkyl
- benzo
- group
- carboxylic acid
- dicyclohexyl
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- 239000005557 antagonist Substances 0.000 title claims abstract 3
- TWSIYGATPWEKBK-UHFFFAOYSA-N 4h-1,3-benzodioxine Chemical class C1=CC=C2OCOCC2=C1 TWSIYGATPWEKBK-UHFFFAOYSA-N 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims abstract 17
- 101001038037 Homo sapiens Lysophosphatidic acid receptor 5 Proteins 0.000 claims abstract 8
- 230000005764 inhibitory process Effects 0.000 claims abstract 5
- 208000001435 Thromboembolism Diseases 0.000 claims abstract 4
- 230000004913 activation Effects 0.000 claims abstract 3
- 210000003630 histaminocyte Anatomy 0.000 claims abstract 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract 2
- 102100040404 Lysophosphatidic acid receptor 5 Human genes 0.000 claims abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 2
- 239000003814 drug Substances 0.000 claims abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 44
- 125000001424 substituent group Chemical group 0.000 claims 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 19
- 229910052757 nitrogen Inorganic materials 0.000 claims 17
- 125000001153 fluoro group Chemical group F* 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 16
- 229910052736 halogen Inorganic materials 0.000 claims 14
- 229910052731 fluorine Inorganic materials 0.000 claims 13
- 239000011737 fluorine Substances 0.000 claims 13
- 125000005842 heteroatom Chemical group 0.000 claims 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 11
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 11
- 229910052760 oxygen Inorganic materials 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- 229910052717 sulfur Inorganic materials 0.000 claims 11
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 8
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 229920006395 saturated elastomer Polymers 0.000 claims 6
- -1 (C1-C5) -alkyl Chemical group 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- LXOHISCRPIDIIG-UHFFFAOYSA-N 1,4-dioxine-2-carboxylic acid Chemical compound OC(=O)C1=COC=CO1 LXOHISCRPIDIIG-UHFFFAOYSA-N 0.000 claims 3
- 208000005189 Embolism Diseases 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000002837 carbocyclic group Chemical group 0.000 claims 3
- 150000001924 cycloalkanes Chemical class 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 230000009467 reduction Effects 0.000 claims 3
- 210000003462 vein Anatomy 0.000 claims 3
- KDKJWPODDXVGNR-UHFFFAOYSA-N 6-bromo-4,4-dicyclohexyl-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C(Br)C=C2C1(C1CCCCC1)C1CCCCC1 KDKJWPODDXVGNR-UHFFFAOYSA-N 0.000 claims 2
- WETJKOLTAUGJRY-UHFFFAOYSA-N 6-chloro-4,4-dicyclohexyl-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C(Cl)C=C2C1(C1CCCCC1)C1CCCCC1 WETJKOLTAUGJRY-UHFFFAOYSA-N 0.000 claims 2
- AVMYLGNHPBELGC-UHFFFAOYSA-N 6-chloro-4-cyclohexyl-4-phenyl-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C(Cl)C=C2C1(C=1C=CC=CC=1)C1CCCCC1 AVMYLGNHPBELGC-UHFFFAOYSA-N 0.000 claims 2
- 206010065390 Inflammatory pain Diseases 0.000 claims 2
- 229910019854 Ru—N Inorganic materials 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 208000032109 Transient ischaemic attack Diseases 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 206010000891 acute myocardial infarction Diseases 0.000 claims 2
- 230000033115 angiogenesis Effects 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 201000010875 transient cerebral ischemia Diseases 0.000 claims 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- CGKINPBJKARFLP-UHFFFAOYSA-N 1,1-dicyclohexyl-7,8,9,10-tetrahydrobenzo[f][1,3]benzodioxine-3-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C3CCCCC3=C2C1(C1CCCCC1)C1CCCCC1 CGKINPBJKARFLP-UHFFFAOYSA-N 0.000 claims 1
- YUCIBCCPUGNTDT-UHFFFAOYSA-N 10-benzyl-4,4-dicyclohexylbenzo[g][1,3]benzodioxine-2-carboxylic acid Chemical compound C12=CC=CC=C2C=C2C(C3CCCCC3)(C3CCCCC3)OC(C(=O)O)OC2=C1CC1=CC=CC=C1 YUCIBCCPUGNTDT-UHFFFAOYSA-N 0.000 claims 1
- BIGWXAGEQONZGD-UHFFFAOYSA-N 2h-oxadiazol-5-one Chemical compound O=C1C=NNO1 BIGWXAGEQONZGD-UHFFFAOYSA-N 0.000 claims 1
- WAXRDOOISKVDOT-UHFFFAOYSA-N 4,4-di(cycloheptyl)-6-(trifluoromethoxy)-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C(OC(F)(F)F)C=C2C1(C1CCCCCC1)C1CCCCCC1 WAXRDOOISKVDOT-UHFFFAOYSA-N 0.000 claims 1
- MBUCGUYVKGSEHA-UHFFFAOYSA-N 4,4-dicyclohexyl-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=CC=C2C1(C1CCCCC1)C1CCCCC1 MBUCGUYVKGSEHA-UHFFFAOYSA-N 0.000 claims 1
- JOJGLFXLBYZKGB-UHFFFAOYSA-N 4,4-dicyclohexyl-5,7-difluoro-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC(F)=CC(F)=C2C1(C1CCCCC1)C1CCCCC1 JOJGLFXLBYZKGB-UHFFFAOYSA-N 0.000 claims 1
- PVUPGOUGVPNXRU-UHFFFAOYSA-N 4,4-dicyclohexyl-5-ethoxy-1,3-benzodioxine-2-carboxylic acid Chemical compound C1=2C(OCC)=CC=CC=2OC(C(O)=O)OC1(C1CCCCC1)C1CCCCC1 PVUPGOUGVPNXRU-UHFFFAOYSA-N 0.000 claims 1
- QDVMDMANAAENOD-UHFFFAOYSA-N 4,4-dicyclohexyl-5-methyl-1,3-benzodioxine-2-carboxylic acid Chemical compound C1=2C(C)=CC=CC=2OC(C(O)=O)OC1(C1CCCCC1)C1CCCCC1 QDVMDMANAAENOD-UHFFFAOYSA-N 0.000 claims 1
- LMYZHOYELPVYPT-UHFFFAOYSA-N 4,4-dicyclohexyl-6-(3-methoxyphenoxy)-1,3-benzodioxine-2-carboxylic acid Chemical compound COC1=CC=CC(OC=2C=C3C(C4CCCCC4)(C4CCCCC4)OC(OC3=CC=2)C(O)=O)=C1 LMYZHOYELPVYPT-UHFFFAOYSA-N 0.000 claims 1
- OJZKUQVZXKOGDE-UHFFFAOYSA-N 4,4-dicyclohexyl-6-(trifluoromethoxy)-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C(OC(F)(F)F)C=C2C1(C1CCCCC1)C1CCCCC1 OJZKUQVZXKOGDE-UHFFFAOYSA-N 0.000 claims 1
- ZOLCCSWVSQMFBG-UHFFFAOYSA-N 4,4-dicyclohexyl-6-(trifluoromethyl)-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C(C(F)(F)F)C=C2C1(C1CCCCC1)C1CCCCC1 ZOLCCSWVSQMFBG-UHFFFAOYSA-N 0.000 claims 1
- JUGCDSDJNBWLJX-UHFFFAOYSA-N 4,4-dicyclohexyl-6-fluoro-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C(F)C=C2C1(C1CCCCC1)C1CCCCC1 JUGCDSDJNBWLJX-UHFFFAOYSA-N 0.000 claims 1
- UNPSUVUWCYRLAV-UHFFFAOYSA-N 4,4-dicyclohexyl-6-iodo-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C(I)C=C2C1(C1CCCCC1)C1CCCCC1 UNPSUVUWCYRLAV-UHFFFAOYSA-N 0.000 claims 1
- APFALXFHUMONES-UHFFFAOYSA-N 4,4-dicyclohexyl-6-methoxy-1,3-benzodioxine-2-carboxylic acid Chemical compound C12=CC(OC)=CC=C2OC(C(O)=O)OC1(C1CCCCC1)C1CCCCC1 APFALXFHUMONES-UHFFFAOYSA-N 0.000 claims 1
- DCMVRCLSDLQDJL-UHFFFAOYSA-N 4,4-dicyclohexyl-6-methyl-1,3-benzodioxine-2-carboxylic acid Chemical compound C12=CC(C)=CC=C2OC(C(O)=O)OC1(C1CCCCC1)C1CCCCC1 DCMVRCLSDLQDJL-UHFFFAOYSA-N 0.000 claims 1
- UYEBYMXVPXATKI-UHFFFAOYSA-N 4,4-dicyclohexyl-6-phenyl-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C(C=3C=CC=CC=3)C=C2C1(C1CCCCC1)C1CCCCC1 UYEBYMXVPXATKI-UHFFFAOYSA-N 0.000 claims 1
- VUGKJOIJENCQHI-UHFFFAOYSA-N 4,4-dicyclohexyl-6-pyridin-3-yloxy-1,3-benzodioxine-2-carboxylic acid Chemical compound C1=C2C(C3CCCCC3)(C3CCCCC3)OC(C(=O)O)OC2=CC=C1OC1=CC=CN=C1 VUGKJOIJENCQHI-UHFFFAOYSA-N 0.000 claims 1
- PQKIXWFIZHKPGF-UHFFFAOYSA-N 4,4-dicyclohexyl-6-pyrrolidin-1-ylsulfonyl-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C(S(=O)(=O)N3CCCC3)C=C2C1(C1CCCCC1)C1CCCCC1 PQKIXWFIZHKPGF-UHFFFAOYSA-N 0.000 claims 1
- ZTMLYBVFVDTKGY-UHFFFAOYSA-N 4,4-dicyclohexyl-7-(diethylamino)-1,3-benzodioxine-2-carboxylic acid Chemical compound C=1C(N(CC)CC)=CC=C2C=1OC(C(O)=O)OC2(C1CCCCC1)C1CCCCC1 ZTMLYBVFVDTKGY-UHFFFAOYSA-N 0.000 claims 1
- ISFWOCTVLCBYSR-UHFFFAOYSA-N 4,4-dicyclohexyl-7-(dimethylamino)-1,3-benzodioxine-2-carboxylic acid Chemical compound C=1C(N(C)C)=CC=C2C=1OC(C(O)=O)OC2(C1CCCCC1)C1CCCCC1 ISFWOCTVLCBYSR-UHFFFAOYSA-N 0.000 claims 1
- ZYHRODKZKDHELH-UHFFFAOYSA-N 4,4-dicyclohexyl-7-methoxy-1,3-benzodioxine-2-carboxylic acid Chemical compound C=1C(OC)=CC=C2C=1OC(C(O)=O)OC2(C1CCCCC1)C1CCCCC1 ZYHRODKZKDHELH-UHFFFAOYSA-N 0.000 claims 1
- CBGGTXULLJKPGU-UHFFFAOYSA-N 4,4-dicyclohexyl-7-methoxy-5-methyl-1,3-benzodioxine-2-carboxylic acid Chemical compound C=1C(OC)=CC(C)=C2C=1OC(C(O)=O)OC2(C1CCCCC1)C1CCCCC1 CBGGTXULLJKPGU-UHFFFAOYSA-N 0.000 claims 1
- ROUBXFAVLIQQFT-UHFFFAOYSA-N 4,4-dicyclohexyl-7-methyl-1,3-benzodioxine-2-carboxylic acid Chemical compound C=1C(C)=CC=C2C=1OC(C(O)=O)OC2(C1CCCCC1)C1CCCCC1 ROUBXFAVLIQQFT-UHFFFAOYSA-N 0.000 claims 1
- JQUBLGPIULPKCS-UHFFFAOYSA-N 4,4-dicyclohexyl-7-phenylmethoxy-1,3-benzodioxine-2-carboxylic acid Chemical compound C=1C=C2C(C3CCCCC3)(C3CCCCC3)OC(C(=O)O)OC2=CC=1OCC1=CC=CC=C1 JQUBLGPIULPKCS-UHFFFAOYSA-N 0.000 claims 1
- DBQKLTSTMBXCTA-UHFFFAOYSA-N 4,4-dicyclohexyl-7-pyrrol-1-yl-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC(N3C=CC=C3)=CC=C2C1(C1CCCCC1)C1CCCCC1 DBQKLTSTMBXCTA-UHFFFAOYSA-N 0.000 claims 1
- WYEOQDHXVWKTDD-UHFFFAOYSA-N 4,4-dicyclohexyl-8-(trifluoromethoxy)-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=C(OC(F)(F)F)C=CC=C2C1(C1CCCCC1)C1CCCCC1 WYEOQDHXVWKTDD-UHFFFAOYSA-N 0.000 claims 1
- NTAQXGSXPPBJFK-UHFFFAOYSA-N 4,4-dicyclohexyl-8-fluoro-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=C(F)C=CC=C2C1(C1CCCCC1)C1CCCCC1 NTAQXGSXPPBJFK-UHFFFAOYSA-N 0.000 claims 1
- IXDXBIUPFXTVBB-UHFFFAOYSA-N 4,4-dicyclohexyl-8-methoxy-1,3-benzodioxine-2-carboxylic acid Chemical compound COC1=CC=CC2=C1OC(C(O)=O)OC2(C1CCCCC1)C1CCCCC1 IXDXBIUPFXTVBB-UHFFFAOYSA-N 0.000 claims 1
- YFKGJAVKSKZPSC-UHFFFAOYSA-N 4,4-dicyclohexyl-8-methyl-1,3-benzodioxine-2-carboxylic acid Chemical compound CC1=CC=CC2=C1OC(C(O)=O)OC2(C1CCCCC1)C1CCCCC1 YFKGJAVKSKZPSC-UHFFFAOYSA-N 0.000 claims 1
- CNOGCZUOGVSHQT-UHFFFAOYSA-N 4,4-dicyclohexylbenzo[g][1,3]benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC3=CC=CC=C3C=C2C1(C1CCCCC1)C1CCCCC1 CNOGCZUOGVSHQT-UHFFFAOYSA-N 0.000 claims 1
- DZTYTOKNBZNHIB-UHFFFAOYSA-N 5-(6-chloro-4,4-dicyclohexyl-1,3-benzodioxin-2-yl)-2h-tetrazole Chemical compound C12=CC(Cl)=CC=C2OC(C2=NNN=N2)OC1(C1CCCCC1)C1CCCCC1 DZTYTOKNBZNHIB-UHFFFAOYSA-N 0.000 claims 1
- DHKAHPFOIXOWHE-UHFFFAOYSA-N 5-(6-chloro-4,4-dicyclohexyl-1,3-benzodioxin-2-yl)-3h-1,3,4-oxadiazol-2-one Chemical compound C12=CC(Cl)=CC=C2OC(C=2OC(=O)NN=2)OC1(C1CCCCC1)C1CCCCC1 DHKAHPFOIXOWHE-UHFFFAOYSA-N 0.000 claims 1
- QIFNMQAHOULZJM-UHFFFAOYSA-N 6,8-dichloro-4,4-dicyclohexyl-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=C(Cl)C=C(Cl)C=C2C1(C1CCCCC1)C1CCCCC1 QIFNMQAHOULZJM-UHFFFAOYSA-N 0.000 claims 1
- NRWJQWMWMQRUNW-UHFFFAOYSA-N 6-(3-chlorophenoxy)-4,4-dicyclohexyl-1,3-benzodioxine-2-carboxylic acid Chemical compound C1=C2C(C3CCCCC3)(C3CCCCC3)OC(C(=O)O)OC2=CC=C1OC1=CC=CC(Cl)=C1 NRWJQWMWMQRUNW-UHFFFAOYSA-N 0.000 claims 1
- TWDRWHNYDGJARY-UHFFFAOYSA-N 6-(4-chlorophenoxy)-4,4-dicyclohexyl-1,3-benzodioxine-2-carboxylic acid Chemical compound C1=C2C(C3CCCCC3)(C3CCCCC3)OC(C(=O)O)OC2=CC=C1OC1=CC=C(Cl)C=C1 TWDRWHNYDGJARY-UHFFFAOYSA-N 0.000 claims 1
- MEVCCTSZUVOZOO-UHFFFAOYSA-N 6-bromo-4,4-di(cycloheptyl)-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C(Br)C=C2C1(C1CCCCCC1)C1CCCCCC1 MEVCCTSZUVOZOO-UHFFFAOYSA-N 0.000 claims 1
- JLDUWYSFYXJSOJ-UHFFFAOYSA-N 6-chloro-4,4-di(cycloheptyl)-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C(Cl)C=C2C1(C1CCCCCC1)C1CCCCCC1 JLDUWYSFYXJSOJ-UHFFFAOYSA-N 0.000 claims 1
- MIJGJCGTZZGABX-UHFFFAOYSA-N 6-chloro-4,4-di(cycloheptyl)-7-methyl-1,3-benzodioxine-2-carboxylic acid Chemical compound C1=2C=C(Cl)C(C)=CC=2OC(C(O)=O)OC1(C1CCCCCC1)C1CCCCCC1 MIJGJCGTZZGABX-UHFFFAOYSA-N 0.000 claims 1
- PSQPVSZHYMTKTM-UHFFFAOYSA-N 6-chloro-4,4-di(cyclooctyl)-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C(Cl)C=C2C1(C1CCCCCCC1)C1CCCCCCC1 PSQPVSZHYMTKTM-UHFFFAOYSA-N 0.000 claims 1
- KOLNJYAVUKRGBP-UHFFFAOYSA-N 6-chloro-4,4-dicyclohexyl-2-methyl-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C)(C(O)=O)OC2=CC=C(Cl)C=C2C1(C1CCCCC1)C1CCCCC1 KOLNJYAVUKRGBP-UHFFFAOYSA-N 0.000 claims 1
- UNRMFSCCXVRPDR-UHFFFAOYSA-N 6-chloro-4,4-dicyclohexyl-5-fluoro-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C(Cl)C(F)=C2C1(C1CCCCC1)C1CCCCC1 UNRMFSCCXVRPDR-UHFFFAOYSA-N 0.000 claims 1
- NQYVUFAEKZROKZ-UHFFFAOYSA-N 6-chloro-4,4-dicyclohexyl-7-fluoro-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC(F)=C(Cl)C=C2C1(C1CCCCC1)C1CCCCC1 NQYVUFAEKZROKZ-UHFFFAOYSA-N 0.000 claims 1
- WYYPLKWWWOBYMJ-UHFFFAOYSA-N 6-chloro-4,4-dicyclohexyl-7-methoxy-1,3-benzodioxine-2-carboxylic acid Chemical compound C1=2C=C(Cl)C(OC)=CC=2OC(C(O)=O)OC1(C1CCCCC1)C1CCCCC1 WYYPLKWWWOBYMJ-UHFFFAOYSA-N 0.000 claims 1
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- OIUMBTSKKUFBAL-UHFFFAOYSA-N 6-chloro-4-cycloheptyl-4h-1,3-benzodioxine-2-carboxylic acid Chemical compound C12=CC(Cl)=CC=C2OC(C(=O)O)OC1C1CCCCCC1 OIUMBTSKKUFBAL-UHFFFAOYSA-N 0.000 claims 1
- KKJUPNGICOCCDW-UHFFFAOYSA-N 7-N,N-Dimethylamino-1,2,3,4,5-pentathiocyclooctane Chemical compound CN(C)C1CSSSSSC1 KKJUPNGICOCCDW-UHFFFAOYSA-N 0.000 claims 1
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- CSBYNSJIKIGCGU-UHFFFAOYSA-N 7-chloro-4,4-dicyclohexyl-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC(Cl)=CC=C2C1(C1CCCCC1)C1CCCCC1 CSBYNSJIKIGCGU-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 230000002025 microglial effect Effects 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 208000008795 neuromyelitis optica Diseases 0.000 claims 1
- 230000001575 pathological effect Effects 0.000 claims 1
- 230000002093 peripheral effect Effects 0.000 claims 1
- 210000001428 peripheral nervous system Anatomy 0.000 claims 1
- 201000011461 pre-eclampsia Diseases 0.000 claims 1
- 230000002035 prolonged effect Effects 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 208000037803 restenosis Diseases 0.000 claims 1
- 230000036303 septic shock Effects 0.000 claims 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims 1
- 230000009885 systemic effect Effects 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 230000002537 thrombolytic effect Effects 0.000 claims 1
- 201000005060 thrombophlebitis Diseases 0.000 claims 1
- 230000001732 thrombotic effect Effects 0.000 claims 1
- 208000009174 transverse myelitis Diseases 0.000 claims 1
- 230000002792 vascular Effects 0.000 claims 1
- 238000007891 venous angioplasty Methods 0.000 claims 1
- 208000004043 venous thromboembolism Diseases 0.000 claims 1
- 230000009385 viral infection Effects 0.000 claims 1
- 210000000274 microglia Anatomy 0.000 abstract 2
- 239000004480 active ingredient Substances 0.000 abstract 1
- 210000001772 blood platelet Anatomy 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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]
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P37/08—Antiallergic agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4245—Oxadiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Cardiology (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12305553 | 2012-05-18 | ||
| PCT/EP2013/060172 WO2013171318A1 (en) | 2012-05-18 | 2013-05-16 | Benzo[1,3]dioxine derivatives and their use as lpar5 antagonists |
| EP13723767.3A EP2850070B1 (en) | 2012-05-18 | 2013-05-16 | Benzo[1,3]dioxine derivatives and their use as lpar5 antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SI2850070T1 true SI2850070T1 (en) | 2018-01-31 |
Family
ID=48468297
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI201330853T SI2850070T1 (en) | 2012-05-18 | 2013-05-16 | Benzo (1,3) dioxin derivatives and their use as LPAR5 antagonists |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US9221784B2 (enExample) |
| EP (1) | EP2850070B1 (enExample) |
| JP (1) | JP6238970B2 (enExample) |
| KR (1) | KR20150016304A (enExample) |
| CN (1) | CN104302633B (enExample) |
| AU (1) | AU2013261719B2 (enExample) |
| BR (1) | BR112014028189A2 (enExample) |
| CA (1) | CA2871545A1 (enExample) |
| ES (1) | ES2649438T3 (enExample) |
| IL (1) | IL235219A (enExample) |
| MX (1) | MX354521B (enExample) |
| PL (1) | PL2850070T3 (enExample) |
| RU (1) | RU2647727C2 (enExample) |
| SG (1) | SG11201407216YA (enExample) |
| SI (1) | SI2850070T1 (enExample) |
| WO (1) | WO2013171318A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20200215085A1 (en) * | 2017-07-19 | 2020-07-09 | Uti Limited Partnership | Method to Abate Acute Airway Hypersensitivity and Asthma Attacks |
| KR20250140741A (ko) | 2024-03-19 | 2025-09-26 | 경북대학교 산학협력단 | 알룰로스를 포함하는 혈전 예방 또는 개선용 조성물 및 이의 이용 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4056540A (en) | 1974-01-01 | 1977-11-01 | Bristol-Myers Company | 4-Phenyl-1,3-benzodioxans |
| US4056450A (en) | 1975-06-30 | 1977-11-01 | M & T Chemicals Inc. | Continuous detinning system |
| FR2424914A2 (fr) * | 1978-05-03 | 1979-11-30 | Roussel Uclaf | Nouveaux derives de (1-3) benzodioxine, un procede pour leur preparation et leur application comme medicaments |
| SE445553B (sv) * | 1978-05-03 | 1986-06-30 | Roussel Uclaf | /4h/-1,3-bensodioxan-2-karboxylsyraderivat |
| GB8310407D0 (en) * | 1982-05-12 | 1983-05-25 | Ici Plc | 1 3 - dioxan -5- ylalkenoic acids |
| FR2704857B1 (fr) * | 1993-05-07 | 1995-06-23 | Adir | Nouvelles benzodioxines substituées, leur procédé de préparation et les compositions pharmaceutiques les contenant. |
| EP1636585B2 (en) | 2003-05-20 | 2012-06-13 | Bayer HealthCare LLC | Diaryl ureas with kinase inhibiting activity |
| CN101124226A (zh) * | 2004-05-07 | 2008-02-13 | 记忆药物公司 | 1h-吲唑、苯并噻唑、1,2-苯并异噁唑、1,2-苯并异噻唑和色酮以及它们的制备和用途 |
| WO2010042600A2 (en) * | 2008-10-08 | 2010-04-15 | The Uab Research Foundation | Photo-activatable therapeutic agents and methods of using |
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2013
- 2013-05-16 SG SG11201407216YA patent/SG11201407216YA/en unknown
- 2013-05-16 BR BR112014028189A patent/BR112014028189A2/pt not_active Application Discontinuation
- 2013-05-16 PL PL13723767T patent/PL2850070T3/pl unknown
- 2013-05-16 MX MX2014014012A patent/MX354521B/es active IP Right Grant
- 2013-05-16 WO PCT/EP2013/060172 patent/WO2013171318A1/en not_active Ceased
- 2013-05-16 RU RU2014151240A patent/RU2647727C2/ru not_active IP Right Cessation
- 2013-05-16 AU AU2013261719A patent/AU2013261719B2/en not_active Ceased
- 2013-05-16 SI SI201330853T patent/SI2850070T1/en unknown
- 2013-05-16 EP EP13723767.3A patent/EP2850070B1/en not_active Not-in-force
- 2013-05-16 CN CN201380025938.2A patent/CN104302633B/zh not_active Expired - Fee Related
- 2013-05-16 KR KR20147033844A patent/KR20150016304A/ko not_active Withdrawn
- 2013-05-16 ES ES13723767.3T patent/ES2649438T3/es active Active
- 2013-05-16 CA CA 2871545 patent/CA2871545A1/en not_active Abandoned
- 2013-05-16 US US14/401,041 patent/US9221784B2/en not_active Expired - Fee Related
- 2013-05-16 JP JP2015512073A patent/JP6238970B2/ja not_active Expired - Fee Related
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2014
- 2014-10-20 IL IL235219A patent/IL235219A/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| IL235219A (en) | 2017-03-30 |
| EP2850070B1 (en) | 2017-08-23 |
| KR20150016304A (ko) | 2015-02-11 |
| RU2014151240A (ru) | 2016-07-10 |
| BR112014028189A2 (pt) | 2017-06-27 |
| MX354521B (es) | 2018-03-08 |
| AU2013261719A1 (en) | 2014-12-18 |
| ES2649438T3 (es) | 2018-01-12 |
| WO2013171318A1 (en) | 2013-11-21 |
| MX2014014012A (es) | 2015-02-12 |
| CN104302633B (zh) | 2016-09-07 |
| CA2871545A1 (en) | 2013-11-21 |
| SG11201407216YA (en) | 2014-12-30 |
| PL2850070T3 (pl) | 2018-01-31 |
| JP2015517515A (ja) | 2015-06-22 |
| RU2647727C2 (ru) | 2018-03-19 |
| AU2013261719B2 (en) | 2017-07-27 |
| US20150111889A1 (en) | 2015-04-23 |
| CN104302633A (zh) | 2015-01-21 |
| EP2850070A1 (en) | 2015-03-25 |
| JP6238970B2 (ja) | 2017-11-29 |
| US9221784B2 (en) | 2015-12-29 |
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