JP2013525369A5 - - Google Patents
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- Publication number
- JP2013525369A5 JP2013525369A5 JP2013506294A JP2013506294A JP2013525369A5 JP 2013525369 A5 JP2013525369 A5 JP 2013525369A5 JP 2013506294 A JP2013506294 A JP 2013506294A JP 2013506294 A JP2013506294 A JP 2013506294A JP 2013525369 A5 JP2013525369 A5 JP 2013525369A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- hydroxy
- trifluoromethyl
- acetamide
- oxadiazol
- 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.)
- Granted
Links
- -1 -CH 2 CH 2 - phenyl Chemical group 0.000 claims 81
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 36
- 125000000217 alkyl group Chemical group 0.000 claims 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 20
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 13
- 125000001424 substituent group Chemical group 0.000 claims 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 11
- 239000003814 drug Substances 0.000 claims 9
- 125000004076 pyridyl group Chemical group 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 7
- OZHGEHHYTPOPTJ-UHFFFAOYSA-N 2-hydroxy-n-[2-(methylamino)-2-oxoethyl]-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]acetamide Chemical compound C1=CC(C(O)C(=O)NCC(=O)NC)=CC=C1C1=NOC(C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)=N1 OZHGEHHYTPOPTJ-UHFFFAOYSA-N 0.000 claims 7
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 7
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 6
- 229940124597 therapeutic agent Drugs 0.000 claims 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 5
- KORQHSDMFVWUTA-UHFFFAOYSA-N N-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]acetamide Chemical compound C(C)(=O)NC1=CC=C(C=C1)C1=NOC(=N1)C1=C(C(=NO1)C1=CC=CC=C1)C(F)(F)F KORQHSDMFVWUTA-UHFFFAOYSA-N 0.000 claims 5
- 125000004965 chloroalkyl group Chemical group 0.000 claims 5
- 125000002883 imidazolyl group Chemical group 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 5
- SGYUYTMWRNCIFM-UHFFFAOYSA-N 2-hydroxy-n-(1,3-oxazol-5-ylmethyl)-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]acetamide Chemical compound C=1C=C(C=2N=C(ON=2)C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)C=CC=1C(O)C(=O)NCC1=CN=CO1 SGYUYTMWRNCIFM-UHFFFAOYSA-N 0.000 claims 4
- RXWTZGGOXAYIKE-UHFFFAOYSA-N 2-hydroxy-n-(2-methylsulfonylethyl)-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]acetamide Chemical compound C1=CC(C(O)C(=O)NCCS(=O)(=O)C)=CC=C1C1=NOC(C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)=N1 RXWTZGGOXAYIKE-UHFFFAOYSA-N 0.000 claims 4
- QDGWCMREKSAGTM-UHFFFAOYSA-N 2-hydroxy-n-[(3-methyl-1,2-oxazol-5-yl)methyl]-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]acetamide Chemical compound O1N=C(C)C=C1CNC(=O)C(O)C1=CC=C(C=2N=C(ON=2)C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)C=C1 QDGWCMREKSAGTM-UHFFFAOYSA-N 0.000 claims 4
- FFXCEEXMUIBSJL-UHFFFAOYSA-N 2-hydroxy-n-[(5-methyl-1,2-oxazol-3-yl)methyl]-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]acetamide Chemical compound O1C(C)=CC(CNC(=O)C(O)C=2C=CC(=CC=2)C=2N=C(ON=2)C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)=N1 FFXCEEXMUIBSJL-UHFFFAOYSA-N 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- WVRKHFSDURCGFL-RSXQAXDFSA-N n-[(1s)-1-cyanoethyl]-2-hydroxy-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]acetamide Chemical compound C1=CC(C(O)C(=O)N[C@@H](C)C#N)=CC=C1C1=NOC(C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)=N1 WVRKHFSDURCGFL-RSXQAXDFSA-N 0.000 claims 4
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 208000023275 Autoimmune disease Diseases 0.000 claims 3
- 208000037976 chronic inflammation Diseases 0.000 claims 3
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- 125000003944 tolyl group Chemical group 0.000 claims 3
- 125000000979 2-amino-2-oxoethyl group Chemical group [H]C([*])([H])C(=O)N([H])[H] 0.000 claims 2
- YXCQSMKIRXQDHI-UHFFFAOYSA-N 2-cyano-2-[[2-hydroxy-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]acetyl]amino]acetamide Chemical compound C1=CC(C(O)C(=O)NC(C(=O)N)C#N)=CC=C1C1=NOC(C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)=N1 YXCQSMKIRXQDHI-UHFFFAOYSA-N 0.000 claims 2
- LWFVBBWRJTULST-UHFFFAOYSA-N 2-hydroxy-2-[4-[5-[1-phenyl-5-(trifluoromethyl)pyrazol-4-yl]-1,2,4-oxadiazol-3-yl]phenyl]-n-propylacetamide Chemical compound C1=CC(C(O)C(=O)NCCC)=CC=C1C1=NOC(C2=C(N(N=C2)C=2C=CC=CC=2)C(F)(F)F)=N1 LWFVBBWRJTULST-UHFFFAOYSA-N 0.000 claims 2
- IXSXWQNCSHUPFE-RSXQAXDFSA-N 2-hydroxy-n-[(2s)-2-hydroxypropyl]-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]acetamide Chemical compound C1=CC(C(O)C(=O)NC[C@@H](O)C)=CC=C1C1=NOC(C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)=N1 IXSXWQNCSHUPFE-RSXQAXDFSA-N 0.000 claims 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 2
- BJMGUFWYMKENNN-UHFFFAOYSA-N 5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazole Chemical compound C1(=CC=CC=C1)C1=NOC(=C1C(F)(F)F)C1=NC=NO1 BJMGUFWYMKENNN-UHFFFAOYSA-N 0.000 claims 2
- 102000004127 Cytokines Human genes 0.000 claims 2
- 108090000695 Cytokines Proteins 0.000 claims 2
- XCJLXFIGEMUOEE-UHFFFAOYSA-N acetamide;2,2,2-trifluoroacetic acid Chemical compound CC(N)=O.OC(=O)C(F)(F)F XCJLXFIGEMUOEE-UHFFFAOYSA-N 0.000 claims 2
- GFZWHAAOIVMHOI-UHFFFAOYSA-N azetidine-3-carboxylic acid Chemical compound OC(=O)C1CNC1 GFZWHAAOIVMHOI-UHFFFAOYSA-N 0.000 claims 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- XRHOJVCCAZUTIN-UHFFFAOYSA-N ethyl 5-[[[2-hydroxy-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]acetyl]amino]methyl]-1h-1,2,4-triazole-3-carboxylate Chemical compound CCOC(=O)C1=NNC(CNC(=O)C(O)C=2C=CC(=CC=2)C=2N=C(ON=2)C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)=N1 XRHOJVCCAZUTIN-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 102000037865 fusion proteins Human genes 0.000 claims 2
- 108020001507 fusion proteins Proteins 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- ORJHDSZAMVIOBT-UHFFFAOYSA-N n-(1,3-dihydroxypropan-2-yl)-2-hydroxy-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]acetamide Chemical compound C1=CC(C(O)C(=O)NC(CO)CO)=CC=C1C1=NOC(C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)=N1 ORJHDSZAMVIOBT-UHFFFAOYSA-N 0.000 claims 2
- LDGOTHYJHKJQQI-UHFFFAOYSA-N n-(1-cyanocyclopropyl)-2-hydroxy-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]acetamide Chemical compound C=1C=C(C=2N=C(ON=2)C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)C=CC=1C(O)C(=O)NC1(C#N)CC1 LDGOTHYJHKJQQI-UHFFFAOYSA-N 0.000 claims 2
- ZZEUBKKBTKTRSV-UHFFFAOYSA-N n-(2-cyanopropan-2-yl)-2-hydroxy-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]acetamide Chemical compound C1=CC(C(O)C(=O)NC(C)(C)C#N)=CC=C1C1=NOC(C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)=N1 ZZEUBKKBTKTRSV-UHFFFAOYSA-N 0.000 claims 2
- BOGJFNQCPQYQRT-DIMJTDRSSA-N n-[(1r)-1-cyano-2-methylpropyl]-2-hydroxy-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]acetamide Chemical compound C1=CC(C(O)C(=O)N[C@H](C(C)C)C#N)=CC=C1C1=NOC(C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)=N1 BOGJFNQCPQYQRT-DIMJTDRSSA-N 0.000 claims 2
- WVRKHFSDURCGFL-GKOGFXNCSA-N n-[(1r)-1-cyanoethyl]-2-hydroxy-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]acetamide Chemical compound C1=CC(C(O)C(=O)N[C@H](C)C#N)=CC=C1C1=NOC(C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)=N1 WVRKHFSDURCGFL-GKOGFXNCSA-N 0.000 claims 2
- BOGJFNQCPQYQRT-DIAVIDTQSA-N n-[(1s)-1-cyano-2-methylpropyl]-2-hydroxy-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]acetamide Chemical compound C1=CC(C(O)C(=O)N[C@@H](C(C)C)C#N)=CC=C1C1=NOC(C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)=N1 BOGJFNQCPQYQRT-DIAVIDTQSA-N 0.000 claims 2
- XTUJICMPBUFOPE-UHFFFAOYSA-N n-[cyano(phenyl)methyl]-2-hydroxy-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]acetamide Chemical compound C=1C=C(C=2N=C(ON=2)C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)C=CC=1C(O)C(=O)NC(C#N)C1=CC=CC=C1 XTUJICMPBUFOPE-UHFFFAOYSA-N 0.000 claims 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000001425 triazolyl group Chemical group 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
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- SOBILORTDNTINR-UHFFFAOYSA-N 2-hydroxy-2-[4-[5-[3-phenyl-4-(trifluoromethyl)-1,2-oxazol-5-yl]-1,2,4-oxadiazol-3-yl]phenyl]-n-(2-pyrazin-2-ylethyl)acetamide Chemical compound C=1C=C(C=2N=C(ON=2)C2=C(C(=NO2)C=2C=CC=CC=2)C(F)(F)F)C=CC=1C(O)C(=O)NCCC1=CN=CC=N1 SOBILORTDNTINR-UHFFFAOYSA-N 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 125000006291 3-hydroxybenzyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])* 0.000 claims 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims 1
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 1
- SKUBGEIEZBPSFJ-UHFFFAOYSA-N FC(F)(F)c1c(cnn1-c1ccccc1)-c1ncno1 Chemical compound FC(F)(F)c1c(cnn1-c1ccccc1)-c1ncno1 SKUBGEIEZBPSFJ-UHFFFAOYSA-N 0.000 claims 1
- 102000003688 G-Protein-Coupled Receptors Human genes 0.000 claims 1
- 108090000045 G-Protein-Coupled Receptors Proteins 0.000 claims 1
- 229940127449 Integrin Receptor Antagonists Drugs 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
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 229940124599 anti-inflammatory drug Drugs 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 claims 1
- 230000001028 anti-proliverative effect Effects 0.000 claims 1
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000003246 corticosteroid Substances 0.000 claims 1
- 229960001334 corticosteroids Drugs 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 231100000433 cytotoxic Toxicity 0.000 claims 1
- 230000001472 cytotoxic effect Effects 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 239000003862 glucocorticoid Substances 0.000 claims 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 1
- 239000010931 gold Substances 0.000 claims 1
- 229910052737 gold Inorganic materials 0.000 claims 1
- 239000003102 growth factor 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 229940043355 kinase inhibitor Drugs 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
- 239000000203 mixture Substances 0.000 claims 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims 1
- 229940021182 non-steroidal anti-inflammatory drug 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
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims 1
- 125000001325 propanoyl group Chemical group O=C([*])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
- 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
- 230000003637 steroidlike Effects 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
- 229940037128 systemic glucocorticoids Drugs 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32731510P | 2010-04-23 | 2010-04-23 | |
| US61/327,315 | 2010-04-23 | ||
| PCT/US2011/033364 WO2011133734A1 (en) | 2010-04-23 | 2011-04-21 | 4 - (5 - isoxazolyl or 5 - pyrrazolyl -1,2,4- oxadiazol - 3 - yl) -mandelic acid amides as sphingosin- 1 - phosphate 1 rreceptor agonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013525369A JP2013525369A (ja) | 2013-06-20 |
| JP2013525369A5 true JP2013525369A5 (https=) | 2014-05-22 |
| JP5735634B2 JP5735634B2 (ja) | 2015-06-17 |
Family
ID=44069927
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013506294A Expired - Fee Related JP5735634B2 (ja) | 2010-04-23 | 2011-04-21 | スフィンゴシン−１−リン酸受容体１アゴニストとしての４−（５−イソオキサゾリルまたは５−ピラゾリル−１，２，４−オキサジアゾール−３−イル）−マンデル酸アミド化合物 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8835470B2 (https=) |
| EP (1) | EP2560969B1 (https=) |
| JP (1) | JP5735634B2 (https=) |
| CN (1) | CN103119038B (https=) |
| ES (1) | ES2548683T3 (https=) |
| WO (1) | WO2011133734A1 (https=) |
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| US8822510B2 (en) | 2010-07-20 | 2014-09-02 | Bristol-Myers Squibb Company | Substituted 3-phenyl-1,2,4-Oxadiazole compounds |
| EP2619190B1 (en) | 2010-09-24 | 2015-08-12 | Bristol-Myers Squibb Company | Substituted oxadiazole compounds and their use as s1p1 agonists |
| EP2635573B1 (en) | 2010-11-03 | 2014-10-01 | Bristol-Myers Squibb Company | Heterocyclic compounds as s1p1 agonists for the treatment of autoimmune and vascular diseases |
| US9115054B2 (en) | 2013-02-21 | 2015-08-25 | Bristol-Myers Squibb Company | Tetrahydronaphthalenyl compounds useful as sipi agonists |
| MX2015014688A (es) * | 2013-04-22 | 2016-02-19 | Abbvie Inc | Tiazoles y usos de los mismos. |
| EP2878339A1 (en) * | 2013-12-02 | 2015-06-03 | Siena Biotech S.p.A. | SIP3 antagonists |
| MA40082B1 (fr) | 2014-08-20 | 2019-09-30 | Bristol Myers Squibb Co | Nouveau compose de substitution sphingosine phosphate utile traitement maladie rhumatisme |
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-
2011
- 2011-04-21 ES ES11717430.0T patent/ES2548683T3/es active Active
- 2011-04-21 US US13/642,755 patent/US8835470B2/en active Active
- 2011-04-21 CN CN201180031281.1A patent/CN103119038B/zh not_active Expired - Fee Related
- 2011-04-21 JP JP2013506294A patent/JP5735634B2/ja not_active Expired - Fee Related
- 2011-04-21 EP EP11717430.0A patent/EP2560969B1/en not_active Not-in-force
- 2011-04-21 WO PCT/US2011/033364 patent/WO2011133734A1/en not_active Ceased
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