JP2004506722A5 - - Google Patents
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- JP2004506722A5 JP2004506722A5 JP2002521433A JP2002521433A JP2004506722A5 JP 2004506722 A5 JP2004506722 A5 JP 2004506722A5 JP 2002521433 A JP2002521433 A JP 2002521433A JP 2002521433 A JP2002521433 A JP 2002521433A JP 2004506722 A5 JP2004506722 A5 JP 2004506722A5
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- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- ethoxy
- oxazol
- propionic acid
- 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.)
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 16
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 12
- 125000000753 cycloalkyl group Chemical group 0.000 description 12
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 9
- -1 1,2,3,4-tetrahydronaphthyl Chemical group 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 125000001475 halogen functional group Chemical group 0.000 description 8
- 125000001072 heteroaryl group Chemical group 0.000 description 8
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- BUTJKZPBLVEJNL-UHFFFAOYSA-N 2-(3,4-dimethylphenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(C)C(C)=C1 BUTJKZPBLVEJNL-UHFFFAOYSA-N 0.000 description 2
- 125000004103 aminoalkyl group Chemical group 0.000 description 2
- 125000004438 haloalkoxy group Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- OWGYDBJOWZBKDM-PGUFJCEWSA-N (2r)-2-methyl-2-(4-methylphenoxy)-3-[4-[2-[5-methyl-2-(3-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound O([C@](C)(CC1=CC=C(C=C1)OCCC=1N=C(OC=1C)C=1C=C(C=CC=1)C=1C=CC=CC=1)C(O)=O)C1=CC=C(C)C=C1 OWGYDBJOWZBKDM-PGUFJCEWSA-N 0.000 description 1
- BMQHLQSJYWHFHJ-PGUFJCEWSA-N (2r)-2-methyl-2-(4-methylphenoxy)-3-[4-[2-[5-methyl-2-(4-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound O([C@](C)(CC1=CC=C(C=C1)OCCC=1N=C(OC=1C)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(O)=O)C1=CC=C(C)C=C1 BMQHLQSJYWHFHJ-PGUFJCEWSA-N 0.000 description 1
- MTFUYHMASMLYGY-MGBGTMOVSA-N (2r)-2-methyl-2-(4-methylphenoxy)-3-[4-[2-[5-methyl-2-(4-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound O([C@](C)(CC1=CC=C(C=C1)OCCC=1N=C(OC=1C)C=1C=CC(=CC=1)C=1SC=CC=1)C(O)=O)C1=CC=C(C)C=C1 MTFUYHMASMLYGY-MGBGTMOVSA-N 0.000 description 1
- IYSUFUOZVISENV-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yloxy)-2-methyl-3-[4-[2-[5-methyl-2-(3-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound N=1C(CCOC=2C=CC(CC(C)(OC=3C=C4OCOC4=CC=3)C(O)=O)=CC=2)=C(C)OC=1C(C=1)=CC=CC=1C1=CC=CC=C1 IYSUFUOZVISENV-UHFFFAOYSA-N 0.000 description 1
- SWADNQWYDSAALT-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yloxy)-2-methyl-3-[4-[2-[5-methyl-2-(3-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound N=1C(CCOC=2C=CC(CC(C)(OC=3C=C4OCOC4=CC=3)C(O)=O)=CC=2)=C(C)OC=1C(C=1)=CC=CC=1C1=CC=CS1 SWADNQWYDSAALT-UHFFFAOYSA-N 0.000 description 1
- WYBYEEFGPCCUJQ-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yloxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound N=1C(CCOC=2C=CC(CC(C)(OC=3C=C4OCOC4=CC=3)C(O)=O)=CC=2)=C(C)OC=1C(C=C1)=CC=C1C1=CC=CC=C1 WYBYEEFGPCCUJQ-UHFFFAOYSA-N 0.000 description 1
- QRYBMPWFECZDOK-UHFFFAOYSA-N 2-(2-fluorophenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC=C1F QRYBMPWFECZDOK-UHFFFAOYSA-N 0.000 description 1
- CZFLATZIUAZOQD-UHFFFAOYSA-N 2-(3,4-difluorophenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(3-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=C(C=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(F)C(F)=C1 CZFLATZIUAZOQD-UHFFFAOYSA-N 0.000 description 1
- HUYITJFINCZYLA-UHFFFAOYSA-N 2-(3,4-difluorophenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(F)C(F)=C1 HUYITJFINCZYLA-UHFFFAOYSA-N 0.000 description 1
- BRTCMAARHAQWKO-UHFFFAOYSA-N 2-(3,4-difluorophenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(F)C(F)=C1 BRTCMAARHAQWKO-UHFFFAOYSA-N 0.000 description 1
- XCMWTYWPVHKIAX-UHFFFAOYSA-N 2-(3,4-dimethylphenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(C)C(C)=C1 XCMWTYWPVHKIAX-UHFFFAOYSA-N 0.000 description 1
- AZNAZJIOOIFBAI-UHFFFAOYSA-N 2-(3-fluorophenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(3-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=C(C=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC(F)=C1 AZNAZJIOOIFBAI-UHFFFAOYSA-N 0.000 description 1
- OGZVZINWQSIAGE-UHFFFAOYSA-N 2-(3-fluorophenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC(F)=C1 OGZVZINWQSIAGE-UHFFFAOYSA-N 0.000 description 1
- FWHLXGIACRDWAA-UHFFFAOYSA-N 2-(3-fluorophenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC(F)=C1 FWHLXGIACRDWAA-UHFFFAOYSA-N 0.000 description 1
- HVBYJDCQVVOJCA-UHFFFAOYSA-N 2-(3-methoxyphenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(3-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound COC1=CC=CC(OC(C)(CC=2C=CC(OCCC3=C(OC(=N3)C=3C=C(C=CC=3)C=3C=CC=CC=3)C)=CC=2)C(O)=O)=C1 HVBYJDCQVVOJCA-UHFFFAOYSA-N 0.000 description 1
- OSCFHDZVHVHBFJ-UHFFFAOYSA-N 2-(3-methoxyphenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound COC1=CC=CC(OC(C)(CC=2C=CC(OCCC3=C(OC(=N3)C=3C=CC(=CC=3)C=3C=CC=CC=3)C)=CC=2)C(O)=O)=C1 OSCFHDZVHVHBFJ-UHFFFAOYSA-N 0.000 description 1
- AGXLJFIKDPNOSP-UHFFFAOYSA-N 2-(3-tert-butylphenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC(C(C)(C)C)=C1 AGXLJFIKDPNOSP-UHFFFAOYSA-N 0.000 description 1
- XRHXQUISMYJHRH-UHFFFAOYSA-N 2-(3-tert-butylphenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC(C(C)(C)C)=C1 XRHXQUISMYJHRH-UHFFFAOYSA-N 0.000 description 1
- UNBMYBLYWTUOST-UHFFFAOYSA-N 2-(4-chlorophenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(3-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=C(C=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(Cl)C=C1 UNBMYBLYWTUOST-UHFFFAOYSA-N 0.000 description 1
- ZIPDTULWNLDTGL-UHFFFAOYSA-N 2-(4-chlorophenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(3-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=C(C=CC=2)C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(Cl)C=C1 ZIPDTULWNLDTGL-UHFFFAOYSA-N 0.000 description 1
- IWPWLTHKDQSYRC-UHFFFAOYSA-N 2-(4-chlorophenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(Cl)C=C1 IWPWLTHKDQSYRC-UHFFFAOYSA-N 0.000 description 1
- LTPUWBBEPNBCSK-UHFFFAOYSA-N 2-(4-cyclohexylphenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(3-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=C(C=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC(C=C1)=CC=C1C1CCCCC1 LTPUWBBEPNBCSK-UHFFFAOYSA-N 0.000 description 1
- MROJJKRXUSSSTL-UHFFFAOYSA-N 2-(4-cyclohexylphenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC(C=C1)=CC=C1C1CCCCC1 MROJJKRXUSSSTL-UHFFFAOYSA-N 0.000 description 1
- SLFXWPXDNFZHBG-UHFFFAOYSA-N 2-(4-fluorophenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(3-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=C(C=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(F)C=C1 SLFXWPXDNFZHBG-UHFFFAOYSA-N 0.000 description 1
- BOZAAQICFMIWTE-UHFFFAOYSA-N 2-(4-fluorophenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(F)C=C1 BOZAAQICFMIWTE-UHFFFAOYSA-N 0.000 description 1
- HAKDKTDSJACAOA-UHFFFAOYSA-N 2-(4-fluorophenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(F)C=C1 HAKDKTDSJACAOA-UHFFFAOYSA-N 0.000 description 1
- KKJOYXBGTOKKBA-UHFFFAOYSA-N 2-(4-tert-butylphenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(3-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=C(C=CC=2)C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(C(C)(C)C)C=C1 KKJOYXBGTOKKBA-UHFFFAOYSA-N 0.000 description 1
- XBODSIUAAXUZHG-UHFFFAOYSA-N 2-(4-tert-butylphenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(3-thiophen-3-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=C(C=CC=2)C2=CSC=C2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(C(C)(C)C)C=C1 XBODSIUAAXUZHG-UHFFFAOYSA-N 0.000 description 1
- VTWJKQYXKKKFOF-UHFFFAOYSA-N 2-(4-tert-butylphenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(C(C)(C)C)C=C1 VTWJKQYXKKKFOF-UHFFFAOYSA-N 0.000 description 1
- WGXNKBOJGSHXSX-UHFFFAOYSA-N 2-[[4-[2-[5-methyl-2-(3-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]methyl]-2-phenoxybutanoic acid Chemical compound C=1C=CC=CC=1OC(C(O)=O)(CC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C(C=1)=CC=CC=1C1=CC=CC=C1 WGXNKBOJGSHXSX-UHFFFAOYSA-N 0.000 description 1
- UBIXGNKRQAIXQL-UHFFFAOYSA-N 2-[[4-[2-[5-methyl-2-(3-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]methyl]-2-phenoxyhexanoic acid Chemical compound C=1C=CC=CC=1OC(C(O)=O)(CCCC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C(C=1)=CC=CC=1C1=CC=CC=C1 UBIXGNKRQAIXQL-UHFFFAOYSA-N 0.000 description 1
- DFDQRLJVQNNCQG-UHFFFAOYSA-N 2-[[4-[2-[5-methyl-2-(3-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]methyl]-2-phenoxybutanoic acid Chemical compound C=1C=CC=CC=1OC(C(O)=O)(CC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C(C=1)=CC=CC=1C1=CC=CS1 DFDQRLJVQNNCQG-UHFFFAOYSA-N 0.000 description 1
- CBIGYLQUUACDNX-UHFFFAOYSA-N 2-[[4-[2-[5-methyl-2-(3-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]methyl]-2-phenoxyhexanoic acid Chemical compound C=1C=CC=CC=1OC(C(O)=O)(CCCC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C(C=1)=CC=CC=1C1=CC=CS1 CBIGYLQUUACDNX-UHFFFAOYSA-N 0.000 description 1
- FRVNFDUZXBYFTE-UHFFFAOYSA-N 2-[[4-[2-[5-methyl-2-(4-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]methyl]-2-phenoxybutanoic acid Chemical compound C=1C=CC=CC=1OC(C(O)=O)(CC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C(C=C1)=CC=C1C1=CC=CC=C1 FRVNFDUZXBYFTE-UHFFFAOYSA-N 0.000 description 1
- XEBAZFCWDSVERF-UHFFFAOYSA-N 2-[[4-[2-[5-methyl-2-(4-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]methyl]-2-phenoxyhexanoic acid Chemical compound C=1C=CC=CC=1OC(C(O)=O)(CCCC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C(C=C1)=CC=C1C1=CC=CC=C1 XEBAZFCWDSVERF-UHFFFAOYSA-N 0.000 description 1
- AKMKLBMKLLQGBK-UHFFFAOYSA-N 2-methyl-2-(3-methylphenoxy)-3-[4-[2-[5-methyl-2-(3-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=C(C=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC(C)=C1 AKMKLBMKLLQGBK-UHFFFAOYSA-N 0.000 description 1
- NTPWLXYSCVDGHT-UHFFFAOYSA-N 2-methyl-2-(3-methylphenoxy)-3-[4-[2-[5-methyl-2-(4-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC(C)=C1 NTPWLXYSCVDGHT-UHFFFAOYSA-N 0.000 description 1
- LAQQWWJAYLBUGN-UHFFFAOYSA-N 2-methyl-2-(3-methylphenoxy)-3-[4-[2-[5-methyl-2-(4-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC(C)=C1 LAQQWWJAYLBUGN-UHFFFAOYSA-N 0.000 description 1
- UMUZXAUEVJEFEJ-UHFFFAOYSA-N 2-methyl-3-[4-[2-[5-methyl-2-(3-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]-3-propylphenyl]-2-phenoxypropanoic acid Chemical compound C=1C=C(OCCC2=C(OC(=N2)C=2C=C(C=CC=2)C=2C=CC=CC=2)C)C(CCC)=CC=1CC(C)(C(O)=O)OC1=CC=CC=C1 UMUZXAUEVJEFEJ-UHFFFAOYSA-N 0.000 description 1
- MCQPNYOFBNCZCN-UHFFFAOYSA-N 2-methyl-3-[4-[2-[5-methyl-2-(3-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]naphthalen-1-yl]-2-phenoxypropanoic acid Chemical compound CC=1OC(C=2C=C(C=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C1=CC=CC=C11)=CC=C1CC(C)(C(O)=O)OC1=CC=CC=C1 MCQPNYOFBNCZCN-UHFFFAOYSA-N 0.000 description 1
- FHUMZVOUCPWGBH-UHFFFAOYSA-N 2-methyl-3-[4-[2-[5-methyl-2-(3-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]-2-[4-(trifluoromethoxy)phenoxy]propanoic acid Chemical compound CC=1OC(C=2C=C(C=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(OC(F)(F)F)C=C1 FHUMZVOUCPWGBH-UHFFFAOYSA-N 0.000 description 1
- QUFDAJDYOPXGGD-UHFFFAOYSA-N 2-methyl-3-[4-[2-[5-methyl-2-(3-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]-2-phenoxypropanoic acid Chemical compound CC=1OC(C=2C=C(C=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC=C1 QUFDAJDYOPXGGD-UHFFFAOYSA-N 0.000 description 1
- JKUYHUMOGXWLCU-UHFFFAOYSA-N 2-methyl-3-[4-[2-[5-methyl-2-(3-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]-2-phenoxypropanoic acid Chemical compound CC=1OC(C=2C=C(C=CC=2)C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC=C1 JKUYHUMOGXWLCU-UHFFFAOYSA-N 0.000 description 1
- RIXXENNLVMJOJD-UHFFFAOYSA-N 2-methyl-3-[4-[2-[5-methyl-2-(3-thiophen-3-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]-2-phenoxypropanoic acid Chemical compound CC=1OC(C=2C=C(C=CC=2)C2=CSC=C2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC=C1 RIXXENNLVMJOJD-UHFFFAOYSA-N 0.000 description 1
- GBOYHTOPFLOCHU-UHFFFAOYSA-N 2-methyl-3-[4-[2-[5-methyl-2-(4-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]naphthalen-1-yl]-2-phenoxypropanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C1=CC=CC=C11)=CC=C1CC(C)(C(O)=O)OC1=CC=CC=C1 GBOYHTOPFLOCHU-UHFFFAOYSA-N 0.000 description 1
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- FBVJKDCUAUJHRQ-UHFFFAOYSA-N 2-methyl-3-[4-[2-[5-methyl-2-(4-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]-3-propylphenyl]-2-phenoxypropanoic acid Chemical compound C=1C=C(OCCC2=C(OC(=N2)C=2C=CC(=CC=2)C=2SC=CC=2)C)C(CCC)=CC=1CC(C)(C(O)=O)OC1=CC=CC=C1 FBVJKDCUAUJHRQ-UHFFFAOYSA-N 0.000 description 1
- KHRYKWRQHQIPEU-UHFFFAOYSA-N 2-methyl-3-[4-[2-[5-methyl-2-(4-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]naphthalen-1-yl]-2-phenoxypropanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2SC=CC=2)=NC=1CCOC(C1=CC=CC=C11)=CC=C1CC(C)(C(O)=O)OC1=CC=CC=C1 KHRYKWRQHQIPEU-UHFFFAOYSA-N 0.000 description 1
- OSOCRAKEOIFNIR-UHFFFAOYSA-N 2-methyl-3-[4-[2-[5-methyl-2-(4-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]-2-[3-(trifluoromethyl)phenoxy]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC(C(F)(F)F)=C1 OSOCRAKEOIFNIR-UHFFFAOYSA-N 0.000 description 1
- ARIJJRAOPWDBMS-UHFFFAOYSA-N 2-methyl-3-[4-[2-[5-methyl-2-(4-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]-2-[4-(trifluoromethoxy)phenoxy]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(OC(F)(F)F)C=C1 ARIJJRAOPWDBMS-UHFFFAOYSA-N 0.000 description 1
- UYHJZSKFRUDZLC-UHFFFAOYSA-N 2-methyl-3-[4-[2-[5-methyl-2-(4-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]-2-[4-(trifluoromethyl)phenoxy]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(C(F)(F)F)C=C1 UYHJZSKFRUDZLC-UHFFFAOYSA-N 0.000 description 1
- HFRGYXNORQFOJZ-UHFFFAOYSA-N 2-methyl-3-[4-[2-[5-methyl-2-(4-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]-2-phenoxypropanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC=C1 HFRGYXNORQFOJZ-UHFFFAOYSA-N 0.000 description 1
- QYQNLKZSJZBWEQ-UHFFFAOYSA-N 3-[3-methoxy-4-[2-[5-methyl-2-(3-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]-2-methyl-2-phenoxypropanoic acid Chemical compound C=1C=C(OCCC2=C(OC(=N2)C=2C=C(C=CC=2)C=2C=CC=CC=2)C)C(OC)=CC=1CC(C)(C(O)=O)OC1=CC=CC=C1 QYQNLKZSJZBWEQ-UHFFFAOYSA-N 0.000 description 1
- ZYVNJLAJWFFCBV-UHFFFAOYSA-N 3-[3-methoxy-4-[2-[5-methyl-2-(4-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]-2-methyl-2-phenoxypropanoic acid Chemical compound C=1C=C(OCCC2=C(OC(=N2)C=2C=CC(=CC=2)C=2C=CC=CC=2)C)C(OC)=CC=1CC(C)(C(O)=O)OC1=CC=CC=C1 ZYVNJLAJWFFCBV-UHFFFAOYSA-N 0.000 description 1
- LSGXPXMAVLVZQK-UHFFFAOYSA-N 3-[3-methoxy-4-[2-[5-methyl-2-(4-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]-2-methyl-2-phenoxypropanoic acid Chemical compound C=1C=C(OCCC2=C(OC(=N2)C=2C=CC(=CC=2)C=2SC=CC=2)C)C(OC)=CC=1CC(C)(C(O)=O)OC1=CC=CC=C1 LSGXPXMAVLVZQK-UHFFFAOYSA-N 0.000 description 1
- OUDVQFHXCHLCBP-UHFFFAOYSA-N 3-[4-[2-[2-[3-(4-fluorophenyl)phenyl]-5-methyl-1,3-oxazol-4-yl]ethoxy]phenyl]-2-methyl-2-phenoxypropanoic acid Chemical compound CC=1OC(C=2C=C(C=CC=2)C=2C=CC(F)=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC=C1 OUDVQFHXCHLCBP-UHFFFAOYSA-N 0.000 description 1
- 0 C*c(c(*)c(*)c(*)c1*)c1OC(*)(Cc(c(*)c1*)c(*)c(*)c1O*(C)C*(C)c1c(*)[o]c(-c(c(*)c2*)c(*)c(*)c2N)n1)C(*)=O Chemical compound C*c(c(*)c(*)c(*)c1*)c1OC(*)(Cc(c(*)c1*)c(*)c(*)c1O*(C)C*(C)c1c(*)[o]c(-c(c(*)c2*)c(*)c(*)c2N)n1)C(*)=O 0.000 description 1
- HWFYMUXPMKXPQV-UHFFFAOYSA-N CC(C(O)=O)C(C=C1)=CC=C1OCCC1=C(C)OC(C(C=C2)=CC=C2C2=CC=CS2)=N1 Chemical compound CC(C(O)=O)C(C=C1)=CC=C1OCCC1=C(C)OC(C(C=C2)=CC=C2C2=CC=CS2)=N1 HWFYMUXPMKXPQV-UHFFFAOYSA-N 0.000 description 1
- ROEXYNAIBIIVEY-UHFFFAOYSA-N CC(C(O)=O)C(C=C1)=CC=C1OCCC1=C(C)OC(C2=CC(C3=CC=CS3)=CC=C2)=N1 Chemical compound CC(C(O)=O)C(C=C1)=CC=C1OCCC1=C(C)OC(C2=CC(C3=CC=CS3)=CC=C2)=N1 ROEXYNAIBIIVEY-UHFFFAOYSA-N 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22745600P | 2000-08-23 | 2000-08-23 | |
| PCT/US2001/022617 WO2002016332A1 (en) | 2000-08-23 | 2001-08-23 | Oxazolyl-arylpropionic acid derivatives and their use as ppar agonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004506722A JP2004506722A (ja) | 2004-03-04 |
| JP2004506722A5 true JP2004506722A5 (enExample) | 2008-10-09 |
Family
ID=22853183
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002521433A Withdrawn JP2004506722A (ja) | 2000-08-23 | 2001-08-23 | ペルオキシソーム増殖因子活性化受容体の調節方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7176224B2 (enExample) |
| EP (1) | EP1313717B1 (enExample) |
| JP (1) | JP2004506722A (enExample) |
| AT (1) | ATE375985T1 (enExample) |
| AU (1) | AU2001284660A1 (enExample) |
| CA (1) | CA2418134A1 (enExample) |
| DE (1) | DE60131001T2 (enExample) |
| ES (1) | ES2295200T3 (enExample) |
| MX (1) | MXPA03001610A (enExample) |
| WO (1) | WO2002016332A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA03001558A (es) | 2000-08-23 | 2003-06-06 | Lilly Co Eli | Agonistas del receptor activado del proliferador de peroxisoma. |
| CA2420178A1 (en) | 2000-08-23 | 2002-03-07 | Eli Lilly And Company | Oxazolyl-aryloxyacetic acid derivatives and their use as ppar agonists |
| IL158873A0 (en) * | 2001-06-07 | 2004-05-12 | Lilly Co Eli | Modulators of peroxisome proliferator activated receptors |
| IL159002A0 (en) * | 2001-06-07 | 2004-05-12 | Lilly Co Eli | Modulators of peroxisome proliferator activated receptors (ppar) |
| ES2326411T3 (es) * | 2001-10-12 | 2009-10-09 | Nippon Chemiphar Co., Ltd. | Activador del receptor delta activado por proliferadores de peroxisomas. |
| US20050080115A1 (en) * | 2002-10-28 | 2005-04-14 | Lone Jeppesen | Novel compounds, their preparation and use |
| CA2503117C (en) * | 2002-11-08 | 2010-12-21 | F. Hoffmann-La Roche Ag | Substituted 4-alkoxyoxazol derivatives as ppar agonists |
| US7192970B2 (en) * | 2002-11-26 | 2007-03-20 | Chipscreen Biosciences, Ltd. | Noncyclic 1,3-dicarbonyl compounds as dual PPAR agonists with potent antihyperglycemic and antihyperlipidemic activity |
| BRPI0407180A (pt) | 2003-02-14 | 2006-02-07 | Lilly Co Eli | Composto, composição farmacêutica, métodos para modular um receptor ativado pelo proliferador de peroxissoma, para tratar ou prevenir uma doença ou condição, para diminuir a glicose no sangue em um mamìfero, para tratar ou prevenir diabetes mellitus, doença cardiovascular e sìndrome x em um mamìfero, e, uso de um composto |
| DE102004060227B3 (de) * | 2004-12-15 | 2006-07-20 | Sanofi-Aventis Deutschland Gmbh | Verfahren zur Herstellung von Oxazolen durch Kondensation von aromatischen Aldehyden mit α-Ketoximen zu N-Oxiden und nachfolgende Reaktion mit aktivierten Säurederivaten |
| WO2007013694A1 (ja) * | 2005-07-29 | 2007-02-01 | Takeda Pharmaceutical Company Limited | フェノキシアルカン酸化合物 |
| MY156174A (en) | 2009-08-05 | 2016-01-15 | Daiichi Sankyo Co Ltd | 4-(1,2,4-dioxazol-3-yl)benzamides for the treatment of diabetes and obesity |
| PL2628733T3 (pl) * | 2010-10-14 | 2015-05-29 | Daiichi Sankyo Co Ltd | Pochodna acylobenzenu |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5089514A (en) * | 1990-06-14 | 1992-02-18 | Pfizer Inc. | 3-coxazolyl [phenyl, chromanyl or benzofuranyl]-2-hydroxypropionic acid derivatives and analogs as hypoglycemic agents |
| US5232945A (en) * | 1992-07-20 | 1993-08-03 | Pfizer Inc. | 3-aryl-2-hydroxypropionic acid derivatives and analogs as antihypertensives |
| US5902726A (en) * | 1994-12-23 | 1999-05-11 | Glaxo Wellcome Inc. | Activators of the nuclear orphan receptor peroxisome proliferator-activated receptor gamma |
| WO1997028115A1 (en) | 1996-02-02 | 1997-08-07 | Merck & Co., Inc. | Antidiabetic agents |
| GB9604242D0 (en) | 1996-02-28 | 1996-05-01 | Glaxo Wellcome Inc | Chemical compounds |
| CZ53699A3 (cs) * | 1996-08-19 | 1999-07-14 | Japan Tobacco Inc. | Deriváty propionové kyseliny a jejich použití |
| KR100620337B1 (ko) | 1998-03-10 | 2006-09-13 | 오노 야꾸힝 고교 가부시키가이샤 | 카르복실산 유도체와 그 유도체를 유효 성분으로서함유하는 약제 |
| AU7073400A (en) * | 1999-08-27 | 2001-03-26 | Eli Lilly And Company | Biaryl-oxa(thia)zole derivatives and their use as ppars modulators |
| JP4316787B2 (ja) | 2000-01-11 | 2009-08-19 | 壽製薬株式会社 | エーテル又はアミド誘導体、その製法並びにそれを含有する糖尿病治療剤、 |
| MXPA03001558A (es) * | 2000-08-23 | 2003-06-06 | Lilly Co Eli | Agonistas del receptor activado del proliferador de peroxisoma. |
| CA2420178A1 (en) | 2000-08-23 | 2002-03-07 | Eli Lilly And Company | Oxazolyl-aryloxyacetic acid derivatives and their use as ppar agonists |
-
2001
- 2001-08-23 US US10/343,187 patent/US7176224B2/en not_active Expired - Fee Related
- 2001-08-23 JP JP2002521433A patent/JP2004506722A/ja not_active Withdrawn
- 2001-08-23 EP EP01963734A patent/EP1313717B1/en not_active Expired - Lifetime
- 2001-08-23 ES ES01963734T patent/ES2295200T3/es not_active Expired - Lifetime
- 2001-08-23 AU AU2001284660A patent/AU2001284660A1/en not_active Abandoned
- 2001-08-23 DE DE60131001T patent/DE60131001T2/de not_active Expired - Lifetime
- 2001-08-23 WO PCT/US2001/022617 patent/WO2002016332A1/en not_active Ceased
- 2001-08-23 AT AT01963734T patent/ATE375985T1/de not_active IP Right Cessation
- 2001-08-23 MX MXPA03001610A patent/MXPA03001610A/es active IP Right Grant
- 2001-08-23 CA CA002418134A patent/CA2418134A1/en not_active Abandoned
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