JP2012515787A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2012515787A5 JP2012515787A5 JP2011548107A JP2011548107A JP2012515787A5 JP 2012515787 A5 JP2012515787 A5 JP 2012515787A5 JP 2011548107 A JP2011548107 A JP 2011548107A JP 2011548107 A JP2011548107 A JP 2011548107A JP 2012515787 A5 JP2012515787 A5 JP 2012515787A5
- Authority
- JP
- Japan
- Prior art keywords
- benzyl
- oxadiazol
- carboxylic acid
- azetidine
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 150000003839 salts Chemical class 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 13
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 208000023275 Autoimmune disease Diseases 0.000 claims 3
- 102000004127 Cytokines Human genes 0.000 claims 3
- 108090000695 Cytokines Proteins 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 208000037976 chronic inflammation Diseases 0.000 claims 3
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims 3
- 125000001188 haloalkyl group Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 102000037865 fusion proteins Human genes 0.000 claims 2
- 108020001507 fusion proteins Proteins 0.000 claims 2
- 239000003102 growth factor Substances 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- WDBHIEGVHFPYLZ-UHFFFAOYSA-N 1-[[2-fluoro-4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C=2N=C(ON=2)C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)C=C1F WDBHIEGVHFPYLZ-UHFFFAOYSA-N 0.000 claims 1
- DJMPVRMOKNBPOD-UHFFFAOYSA-N 1-[[2-methyl-4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound CC1=CC(C=2N=C(ON=2)C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)=CC=C1CN1CC(C(O)=O)C1 DJMPVRMOKNBPOD-UHFFFAOYSA-N 0.000 claims 1
- ZEYFXLMLYUQDRA-UHFFFAOYSA-N 1-[[3-chloro-4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1Cl)=CC=C1C1=NOC(C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)=N1 ZEYFXLMLYUQDRA-UHFFFAOYSA-N 0.000 claims 1
- BWKUVASDAJWATN-UHFFFAOYSA-N 1-[[4-[5-(3-phenyl-4-propyl-1,2-oxazol-5-yl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound CCCC=1C(C=2C=CC=CC=2)=NOC=1C(ON=1)=NC=1C(C=C1)=CC=C1CN1CC(C(O)=O)C1 BWKUVASDAJWATN-UHFFFAOYSA-N 0.000 claims 1
- YIBLFOJWBHUMCJ-UHFFFAOYSA-N 1-[[4-[5-(4,5-diphenyl-1,2-oxazol-3-yl)-1,2,4-oxadiazol-3-yl]-3-(trifluoromethyl)phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1C(F)(F)F)=CC=C1C1=NOC(C=2C(=C(ON=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 YIBLFOJWBHUMCJ-UHFFFAOYSA-N 0.000 claims 1
- HZHVXSADFVTJOJ-UHFFFAOYSA-N 1-[[4-[5-(4,5-diphenyl-1,2-oxazol-3-yl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C=2N=C(ON=2)C=2C(=C(ON=2)C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 HZHVXSADFVTJOJ-UHFFFAOYSA-N 0.000 claims 1
- LFGUWCCYLFPFKJ-UHFFFAOYSA-N 1-[[4-[5-(4-butyl-5-phenyl-1,2-oxazol-3-yl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound CCCCC=1C(C=2ON=C(N=2)C=2C=CC(CN3CC(C3)C(O)=O)=CC=2)=NOC=1C1=CC=CC=C1 LFGUWCCYLFPFKJ-UHFFFAOYSA-N 0.000 claims 1
- USQBYAXALATVIP-UHFFFAOYSA-N 1-[[4-[5-(4-cyclopropyl-5-phenyl-1,2-oxazol-3-yl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C=2N=C(ON=2)C=2C(=C(ON=2)C=2C=CC=CC=2)C2CC2)C=C1 USQBYAXALATVIP-UHFFFAOYSA-N 0.000 claims 1
- GTOHVIRIULGSEK-UHFFFAOYSA-N 1-[[4-[5-(4-ethyl-5-phenyl-1,2-oxazol-3-yl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound CCC=1C(C=2ON=C(N=2)C=2C=CC(CN3CC(C3)C(O)=O)=CC=2)=NOC=1C1=CC=CC=C1 GTOHVIRIULGSEK-UHFFFAOYSA-N 0.000 claims 1
- IADDFFVVBQCWHU-UHFFFAOYSA-N 1-[[4-[5-(4-methoxycarbonyl-3-phenyl-1,2-oxazol-5-yl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound COC(=O)C=1C(C=2C=CC=CC=2)=NOC=1C(ON=1)=NC=1C(C=C1)=CC=C1CN1CC(C(O)=O)C1 IADDFFVVBQCWHU-UHFFFAOYSA-N 0.000 claims 1
- HRPSBHVSFBEQRU-UHFFFAOYSA-N 1-[[4-[5-(4-tert-butyl-5-phenyl-1,2-oxazol-3-yl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound CC(C)(C)C=1C(C=2ON=C(N=2)C=2C=CC(CN3CC(C3)C(O)=O)=CC=2)=NOC=1C1=CC=CC=C1 HRPSBHVSFBEQRU-UHFFFAOYSA-N 0.000 claims 1
- MDZNZQOVDXPWCN-UHFFFAOYSA-N 1-[[4-[5-[3-phenyl-4-(2,2,2-trifluoroethylcarbamoyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C=2N=C(ON=2)C2=C(C(=NO2)C=2C=CC=CC=2)C(=O)NCC(F)(F)F)C=C1 MDZNZQOVDXPWCN-UHFFFAOYSA-N 0.000 claims 1
- IFBHAJWNBNJWRY-UHFFFAOYSA-N 1-[[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]-3-(trifluoromethyl)phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1C(F)(F)F)=CC=C1C1=NOC(C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)=N1 IFBHAJWNBNJWRY-UHFFFAOYSA-N 0.000 claims 1
- RRPYZEWVBYBTJC-UHFFFAOYSA-N 1-[[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C=2N=C(ON=2)C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)C=C1 RRPYZEWVBYBTJC-UHFFFAOYSA-N 0.000 claims 1
- VRKIBLMQZSLKNF-UHFFFAOYSA-N 1-[[4-[5-[4-(1,1-difluoroethyl)-5-phenyl-1,2-oxazol-3-yl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound CC(F)(F)C=1C(C=2ON=C(N=2)C=2C=CC(CN3CC(C3)C(O)=O)=CC=2)=NOC=1C1=CC=CC=C1 VRKIBLMQZSLKNF-UHFFFAOYSA-N 0.000 claims 1
- KDJYQIKYVXNAMT-UHFFFAOYSA-N 1-[[4-[5-[4-(1,1-difluoropropyl)-5-phenyl-1,2-oxazol-3-yl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound CCC(F)(F)C=1C(C=2ON=C(N=2)C=2C=CC(CN3CC(C3)C(O)=O)=CC=2)=NOC=1C1=CC=CC=C1 KDJYQIKYVXNAMT-UHFFFAOYSA-N 0.000 claims 1
- FIQMYTYVSJKMNV-UHFFFAOYSA-N 1-[[4-[5-[4-(2-methylpropyl)-5-phenyl-1,2-oxazol-3-yl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound CC(C)CC=1C(C=2ON=C(N=2)C=2C=CC(CN3CC(C3)C(O)=O)=CC=2)=NOC=1C1=CC=CC=C1 FIQMYTYVSJKMNV-UHFFFAOYSA-N 0.000 claims 1
- SETXXIRDLHEUGQ-UHFFFAOYSA-N 1-[[4-[5-[4-(2-methylpropyl)-5-propyl-1,2-oxazol-3-yl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound CC(C)CC1=C(CCC)ON=C1C1=NC(C=2C=CC(CN3CC(C3)C(O)=O)=CC=2)=NO1 SETXXIRDLHEUGQ-UHFFFAOYSA-N 0.000 claims 1
- LRIFWORMZLCUQS-UHFFFAOYSA-N 1-[[4-[5-[4-(difluoromethyl)-3-phenyl-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C=2N=C(ON=2)C2=C(C(=NO2)C=2C=CC=CC=2)C(F)F)C=C1 LRIFWORMZLCUQS-UHFFFAOYSA-N 0.000 claims 1
- OVVVIWLJHPDLFO-UHFFFAOYSA-N 1-[[4-[5-[4-(methylcarbamoyl)-3-phenyl-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound CNC(=O)C=1C(C=2C=CC=CC=2)=NOC=1C(ON=1)=NC=1C(C=C1)=CC=C1CN1CC(C(O)=O)C1 OVVVIWLJHPDLFO-UHFFFAOYSA-N 0.000 claims 1
- KKZAKGKOIPIRBJ-UHFFFAOYSA-N 1-[[4-[5-[5-(2-methylpropyl)-4-(trifluoromethyl)-1,2-oxazol-3-yl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound FC(F)(F)C1=C(CC(C)C)ON=C1C1=NC(C=2C=CC(CN3CC(C3)C(O)=O)=CC=2)=NO1 KKZAKGKOIPIRBJ-UHFFFAOYSA-N 0.000 claims 1
- SDVLOQHJJPNZLT-UHFFFAOYSA-N 1-[[4-[5-[5-(2-methylpropyl)-4-propyl-1,2-oxazol-3-yl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound CCCC1=C(CC(C)C)ON=C1C1=NC(C=2C=CC(CN3CC(C3)C(O)=O)=CC=2)=NO1 SDVLOQHJJPNZLT-UHFFFAOYSA-N 0.000 claims 1
- IEIGSGQMSWIYKE-UHFFFAOYSA-N 1-[[4-[5-[5-phenyl-4-(3,3,3-trifluoropropyl)-1,2-oxazol-3-yl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C=2N=C(ON=2)C=2C(=C(ON=2)C=2C=CC=CC=2)CCC(F)(F)F)C=C1 IEIGSGQMSWIYKE-UHFFFAOYSA-N 0.000 claims 1
- MVGGESVLDQUSPU-UHFFFAOYSA-N 1-[[4-[5-[5-phenyl-4-(trifluoromethyl)-1,2-oxazol-3-yl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C=2N=C(ON=2)C=2C(=C(ON=2)C=2C=CC=CC=2)C(F)(F)F)C=C1 MVGGESVLDQUSPU-UHFFFAOYSA-N 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- -1 4-substituted imidazo [1,2-A] quinoxalines Chemical class 0.000 claims 1
- NXMSHDWOJXUEQH-UHFFFAOYSA-N 5-[3-[4-[(3-carboxyazetidin-1-yl)methyl]phenyl]-1,2,4-oxadiazol-5-yl]-3-phenyl-1,2-oxazole-4-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C=2N=C(ON=2)C2=C(C(=NO2)C=2C=CC=CC=2)C(O)=O)C=C1 NXMSHDWOJXUEQH-UHFFFAOYSA-N 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
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 229940124599 anti-inflammatory drug Drugs 0.000 claims 1
- 230000001028 anti-proliverative effect Effects 0.000 claims 1
- 239000003443 antiviral agent Substances 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000003246 corticosteroid Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 229940127089 cytotoxic agent Drugs 0.000 claims 1
- 239000002254 cytotoxic agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000003862 glucocorticoid Substances 0.000 claims 1
- XXSMGPRMXLTPCZ-UHFFFAOYSA-N hydroxychloroquine Chemical compound ClC1=CC=C2C(NC(C)CCCN(CCO)CC)=CC=NC2=C1 XXSMGPRMXLTPCZ-UHFFFAOYSA-N 0.000 claims 1
- 229960004171 hydroxychloroquine Drugs 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 102000006495 integrins Human genes 0.000 claims 1
- 108010044426 integrins Proteins 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 claims 1
- 229960004963 mesalazine Drugs 0.000 claims 1
- 230000005937 nuclear translocation Effects 0.000 claims 1
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims 1
- 229960001639 penicillamine Drugs 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 claims 1
- 239000002464 receptor antagonist Substances 0.000 claims 1
- 229940044551 receptor antagonist Drugs 0.000 claims 1
- 102000005962 receptors Human genes 0.000 claims 1
- 108020003175 receptors Proteins 0.000 claims 1
- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 claims 1
- 229960002930 sirolimus Drugs 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
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14682709P | 2009-01-23 | 2009-01-23 | |
| US61/146,827 | 2009-01-23 | ||
| PCT/US2010/021693 WO2010085581A1 (en) | 2009-01-23 | 2010-01-22 | Substituted oxadiazole derivatives as s1p agonists in the treatment of autoimmune and inflammatory diseases |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012515787A JP2012515787A (ja) | 2012-07-12 |
| JP2012515787A5 true JP2012515787A5 (enExample) | 2013-01-10 |
Family
ID=41820292
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011548107A Ceased JP2012515787A (ja) | 2009-01-23 | 2010-01-22 | 自己免疫疾患および炎症性疾患の処置におけるｓ１ｐアゴニストとしての置換オキサジアゾール誘導体 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8354398B2 (enExample) |
| EP (1) | EP2382212B1 (enExample) |
| JP (1) | JP2012515787A (enExample) |
| CN (1) | CN102361867A (enExample) |
| WO (1) | WO2010085581A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012515788A (ja) | 2009-01-23 | 2012-07-12 | ブリストル−マイヤーズ スクイブ カンパニー | 自己免疫疾患および炎症性疾患の処置における、ｓ１ｐアゴニストとしての置換オキサジアゾール誘導体 |
| ES2405054T3 (es) | 2009-01-23 | 2013-05-30 | Bristol-Myers Squibb Company | Derivados de pirazol-1,2,4-oxadiazol como agonistas de esfingosina-1-fosfato |
| US8399451B2 (en) | 2009-08-07 | 2013-03-19 | Bristol-Myers Squibb Company | Heterocyclic compounds |
| WO2011133734A1 (en) * | 2010-04-23 | 2011-10-27 | Bristol-Myers Squibb Company | 4 - (5 - isoxazolyl or 5 - pyrrazolyl -1,2,4- oxadiazol - 3 - yl) -mandelic acid amides as sphingosin- 1 - phosphate 1 rreceptor agonists |
| ES2539256T3 (es) | 2010-07-20 | 2015-06-29 | Bristol-Myers Squibb Company | Compuestos de 3-fenil-1,2,4-oxadiazol sustituidos |
| US9187437B2 (en) | 2010-09-24 | 2015-11-17 | Bristol-Myers Squibb Company | Substituted oxadiazole compounds |
| ES2525298T3 (es) | 2010-11-03 | 2014-12-19 | Bristol-Myers Squibb Company | Compuestos heterocíclicos como agonistas del S1P1 para el tratamiento de enfermedades autoinmunes y vasculares |
| JP2013544831A (ja) * | 2010-12-03 | 2013-12-19 | アラーガン インコーポレイテッド | スフィンゴシン−１−リン酸（ｓ１ｐ）受容体モジュレーターとしての新規アゼチジン誘導体 |
| US8354436B2 (en) * | 2011-01-28 | 2013-01-15 | 4Sc Discovery Gmbh | IL17 and IFN-gamma inhibition for the treatment of autoimmune inflammation |
| US8859598B2 (en) * | 2012-10-04 | 2014-10-14 | Allergan, Inc. | 1, 2, 4-oxadiazoles azetidine derivatives as sphingosine-1 phosphate receptors modulators |
| CN102977046B (zh) * | 2012-11-30 | 2016-01-20 | 石家庄诚志永华显示材料有限公司 | 1,2,4-噁二唑类化合物及其制备方法与应用 |
| UY35338A (es) | 2013-02-21 | 2014-08-29 | Bristol Myers Squibb Company Una Corporación Del Estado De Delaware | Compuestos bicíclicos moduladores de la actividad de s1p1 y composiciones farmacéuticas que los contienen |
| CN103450171B (zh) * | 2013-09-22 | 2015-07-08 | 苏州康乃德生物医药有限公司 | 一种免疫调节化合物、其用途和包含其的药物组合物 |
| UY36274A (es) | 2014-08-20 | 2016-02-29 | Bristol Myers Squibb Company Una Corporación Del Estado De Delaware | Compuestos bicíclicos sustituidos como agonistas selectivos de la actividad del receptor s1p1 acoplado a la proteína g |
| UY37062A (es) * | 2016-01-08 | 2017-08-31 | Syngenta Participations Ag | Derivados de aryl oxadiazol fungicidas |
| AR109304A1 (es) | 2016-08-10 | 2018-11-21 | Sumitomo Chemical Co | Compuesto de oxadiazol y su uso |
| CN112079791A (zh) * | 2020-08-21 | 2020-12-15 | 宁夏农林科学院农业资源与环境研究所（宁夏土壤与植物营养重点实验室） | 单环β-内酰胺类抗生素侧链酸及其酯、其制备方法和应用 |
| CN115233243B (zh) * | 2022-06-27 | 2025-05-16 | 台州学院 | 一种电催化下2,4,5-三取代噁唑衍生物的制备方法 |
Family Cites Families (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4200750A (en) | 1977-01-07 | 1980-04-29 | Westwood Pharmaceuticals Inc. | 4-Substituted imidazo [1,2-a]quinoxalines |
| ATE441654T1 (de) * | 2002-01-18 | 2009-09-15 | Merck & Co Inc | Edg-rezeptoragonisten |
| CA2472680A1 (en) | 2002-01-18 | 2003-07-31 | Merck & Co., Inc. | Selective s1p1/edg1 receptor agonists |
| ATE448193T1 (de) | 2002-01-18 | 2009-11-15 | Merck & Co Inc | ßN-(BENZYL)AMINOALKYL CARBOXYLATE, PHOSPHINATE, PHOSPHONATE UND TETRAZOLE ALS EDG REZEPTORAGONISTENß |
| WO2003073986A2 (en) | 2002-03-01 | 2003-09-12 | Merck & Co., Inc. | Aminoalkylphosphonates and related compounds as edg receptor agonists |
| CA2488117A1 (en) | 2002-06-17 | 2003-12-24 | Merck & Co., Inc. | 1-((5-aryl-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylates and 1-((5-aryl-1,2,4-oxadiazol-3-yl)benzyl)pyrrolidine-3-carboxylates as edg receptor agonists |
| BR0316209A (pt) | 2002-11-15 | 2005-09-27 | Tibotec Pharm Ltd | Indolpiridìnio substituìdo como compostos antiinfecciosos |
| CA2509218C (en) | 2002-12-20 | 2010-09-07 | Merck & Co., Inc. | 1-(amino)indanes and (1,2-dihydro-3-amino)-benzofurans, benzothiophenes and indoles as edg receptor agonists |
| JP2006528980A (ja) * | 2003-05-15 | 2006-12-28 | メルク エンド カムパニー インコーポレーテッド | Ｓ１ｐ受容体作働薬としての３−（２−アミノ−１−アザシクロ）−５−アリール−１，２，４−オキサジアゾール類 |
| BRPI0410439A (pt) | 2003-05-19 | 2006-06-06 | Irm Llc | compostos e composições imunossupressoras |
| AU2004299456B2 (en) | 2003-12-17 | 2010-10-07 | Merck Sharp & Dohme Corp. | (3,4-disubstituted)propanoic carboxylates as S1P (Edg) receptor agonists |
| TW200538433A (en) | 2004-02-24 | 2005-12-01 | Irm Llc | Immunosuppressant compounds and compositiions |
| JP2008517915A (ja) | 2004-10-22 | 2008-05-29 | メルク エンド カムパニー インコーポレーテッド | Ｓ１ｐ受容体アゴニストとしての２−（アリール）アザシクリルメチルカルボキシレート、スルホネート、ホスホネート、ホスフィネート及びヘテロ環 |
| BRPI0607435A2 (pt) | 2005-02-14 | 2010-04-06 | Univ Virginia | composto ou um sal ou éster farmaceuticamente aceitável do mesmo, e, uso de um composto |
| ATE413874T1 (de) | 2005-03-23 | 2008-11-15 | Actelion Pharmaceuticals Ltd | Neue thiophen-derivate als sphingosin-1-phosphat- 1-rezeptorantagonisten |
| WO2006100631A1 (en) | 2005-03-23 | 2006-09-28 | Actelion Pharmaceuticals Ltd | Hydrogenated benzo (c) thiophene derivatives as immunomodulators |
| WO2006115188A1 (ja) | 2005-04-22 | 2006-11-02 | Daiichi Sankyo Company, Limited | ヘテロ環化合物 |
| GB0511684D0 (en) * | 2005-06-08 | 2005-07-13 | Novartis Ag | Organic compounds |
| WO2006131336A1 (en) | 2005-06-08 | 2006-12-14 | Novartis Ag | POLYCYCLIC OXADIAZOLES OR I SOXAZOLES AND THEIR USE AS SlP RECEPTOR LIGANDS |
| MX2008002540A (es) | 2005-08-23 | 2008-03-14 | Irm Llc | Compuestos inmunosupresores y composiciones. |
| JP2009520688A (ja) | 2005-11-23 | 2009-05-28 | エピックス デラウェア， インコーポレイテッド | Ｓ１ｐ受容体調節化合物およびそれらの使用 |
| GB0601744D0 (en) | 2006-01-27 | 2006-03-08 | Novartis Ag | Organic compounds |
| JP5099005B2 (ja) | 2006-04-03 | 2012-12-12 | アステラス製薬株式会社 | ヘテロ化合物 |
| JP2009269819A (ja) | 2006-08-25 | 2009-11-19 | Asahi Kasei Pharma Kk | アミン化合物 |
| TWI408139B (zh) | 2006-09-07 | 2013-09-11 | Actelion Pharmaceuticals Ltd | 新穎噻吩衍生物 |
| PL2069336T3 (pl) | 2006-09-07 | 2013-05-31 | Idorsia Pharmaceuticals Ltd | Pochodne pirydyn-4-ylu jako środki immunomodulujące |
| ES2393412T3 (es) | 2006-09-21 | 2012-12-21 | Actelion Pharmaceuticals Ltd. | Derivados de fenilo y su uso como inmunomoduladores |
| MX2009006304A (es) * | 2006-12-15 | 2009-06-23 | Abbott Lab | Nuevos compuestos de oxadiazol. |
| GB0625648D0 (en) | 2006-12-21 | 2007-01-31 | Glaxo Group Ltd | Compounds |
| CL2007003784A1 (es) | 2006-12-21 | 2008-06-27 | Abbott Lab | Compuestos derivados de 1-amino-3-fenilciclopentano, que son agonistas o antagonistas de uno o mas receptores de la familia s1p; composicion farmaceutica que comprende a dichos compuestos; y su uso para tratar la esclerosis multiple, artritis reumato |
| JP5191497B2 (ja) | 2007-03-21 | 2013-05-08 | エピックス ファーマシューティカルズ，インコーポレイテッド | Ｓ１ｐ受容体調節化合物およびその使用 |
| AU2008253311A1 (en) | 2007-05-18 | 2008-11-27 | Bayer Schering Pharma Aktiengesellshaft | Inhibitors of hypoxia inducible factor (HIF) useful for treating hyper-proliferative disorders and diseases associated with angiogenesis |
| US20090069288A1 (en) | 2007-07-16 | 2009-03-12 | Breinlinger Eric C | Novel therapeutic compounds |
| MX2010003614A (es) | 2007-10-04 | 2010-04-21 | Merck Serono Sa | Compuestos de diarilo oxadiazol. |
| EP2193125B1 (en) | 2007-10-04 | 2017-01-11 | Merck Serono S.A. | Oxadiazole derivatives |
| EP2217594B1 (en) | 2007-11-01 | 2014-01-08 | Actelion Pharmaceuticals Ltd. | Novel pyrimidine derivatives |
| WO2009131090A1 (ja) | 2008-04-21 | 2009-10-29 | 旭化成ファーマ株式会社 | アミノ酸化合物 |
| EP2913326B1 (en) | 2008-05-14 | 2020-07-15 | The Scripps Research Institute | Novel modulators of sphingosine phosphate receptors |
| CA2739303A1 (en) | 2008-10-01 | 2010-04-08 | Synta Pharmaceuticals Corp. | Compounds for inflammation and immune-related uses |
| US8314130B2 (en) | 2008-10-01 | 2012-11-20 | Synta Pharmaceuticals Corp. | Compounds inclunding substituted pyridines for inflammation and immune-related uses |
| WO2010065760A1 (en) | 2008-12-04 | 2010-06-10 | Exelixis, Inc. | Imidazo [1,2a] pyridine derivatives, their use as s1p1 agonists and methods for their production |
| ES2405054T3 (es) | 2009-01-23 | 2013-05-30 | Bristol-Myers Squibb Company | Derivados de pirazol-1,2,4-oxadiazol como agonistas de esfingosina-1-fosfato |
| JP2012515788A (ja) | 2009-01-23 | 2012-07-12 | ブリストル−マイヤーズ スクイブ カンパニー | 自己免疫疾患および炎症性疾患の処置における、ｓ１ｐアゴニストとしての置換オキサジアゾール誘導体 |
-
2010
- 2010-01-22 WO PCT/US2010/021693 patent/WO2010085581A1/en not_active Ceased
- 2010-01-22 US US13/145,730 patent/US8354398B2/en active Active
- 2010-01-22 CN CN2010800132551A patent/CN102361867A/zh active Pending
- 2010-01-22 EP EP10701297.3A patent/EP2382212B1/en not_active Not-in-force
- 2010-01-22 JP JP2011548107A patent/JP2012515787A/ja not_active Ceased
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2012515787A5 (enExample) | ||
| JP2012515788A5 (enExample) | ||
| JP2012515789A5 (enExample) | ||
| JP2014526500A5 (enExample) | ||
| JP2006517939A5 (enExample) | ||
| JP2014526501A5 (enExample) | ||
| AU2014372166B2 (en) | Pharmaceutical combinations | |
| JP2007519649A5 (enExample) | ||
| JP2017504611A5 (enExample) | ||
| JP2009514870A5 (enExample) | ||
| JP2012519160A (ja) | Ｐｄｅ４阻害剤及びｎｓａｉｄを含有する組み合わせ薬 | |
| JP2008500992A5 (enExample) | ||
| JP2018528206A5 (enExample) | ||
| US10189813B2 (en) | Formylated N-heterocyclic derivatives as FGFR4 inhibitors | |
| JP2014513110A5 (enExample) | ||
| JP2016523974A5 (enExample) | ||
| JP2004530705A5 (enExample) | ||
| JP2020516671A5 (enExample) | ||
| JP2013543896A5 (enExample) | ||
| HRP20220619T1 (hr) | Postupci za liječenje ar+ raka dojke | |
| RU2020142739A (ru) | Ингибиторы mdm2 и их комбинации | |
| JP2014531449A5 (enExample) | ||
| JP2012522748A5 (enExample) | ||
| HRP20161116T1 (hr) | NOVI DERIVATI CIKLOHEKSILAMINA KOJI DJELUJU KAO AGONISTI β2 ADRENERGIČKOG RECEPTORA I ANTAGONISTI MUSKARINSKOG ACETILKOLINSKOG RECEPTORA M3 | |
| JP2016534124A5 (enExample) |