JP2007522178A5 - - Google Patents
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- JP2007522178A5 JP2007522178A5 JP2006552575A JP2006552575A JP2007522178A5 JP 2007522178 A5 JP2007522178 A5 JP 2007522178A5 JP 2006552575 A JP2006552575 A JP 2006552575A JP 2006552575 A JP2006552575 A JP 2006552575A JP 2007522178 A5 JP2007522178 A5 JP 2007522178A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- oxy
- benzothien
- acetic acid
- trifluoromethyl
- 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.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims 15
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 101000741788 Homo sapiens Peroxisome proliferator-activated receptor alpha Proteins 0.000 claims 2
- 102100038831 Peroxisome proliferator-activated receptor alpha Human genes 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- -1 (methyloxy) ethylpropyloxy Chemical group 0.000 claims 1
- WHXIFNNKMPBSRB-UHFFFAOYSA-N 2-[2-(trifluoromethyl)-4-[3-[6-(trifluoromethyl)-1-benzothiophen-2-yl]heptylsulfanyl]phenoxy]acetic acid Chemical compound C=1C2=CC=C(C(F)(F)F)C=C2SC=1C(CCCC)CCSC1=CC=C(OCC(O)=O)C(C(F)(F)F)=C1 WHXIFNNKMPBSRB-UHFFFAOYSA-N 0.000 claims 1
- VQASCLSPACGZQA-UHFFFAOYSA-N 2-[2-(trifluoromethyl)-4-[3-[6-(trifluoromethyl)-1-benzothiophen-2-yl]propylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(C(F)(F)F)C(OCC(=O)O)=CC=C1SCCCC1=CC2=CC=C(C(F)(F)F)C=C2S1 VQASCLSPACGZQA-UHFFFAOYSA-N 0.000 claims 1
- YRZCISGCWQPMOS-UHFFFAOYSA-N 2-[2-[3-(3,6-dimethyl-1-benzofuran-2-yl)heptylsulfanyl]-4-methyl-1,3-thiazol-5-yl]acetic acid Chemical compound O1C2=CC(C)=CC=C2C(C)=C1C(CCCC)CCSC1=NC(C)=C(CC(O)=O)S1 YRZCISGCWQPMOS-UHFFFAOYSA-N 0.000 claims 1
- VGXJHTHNYSRSHN-UHFFFAOYSA-N 2-[2-[3-(6-methoxy-3-methyl-1-benzothiophen-2-yl)heptylsulfanyl]-1,3-thiazol-4-yl]acetic acid Chemical compound S1C2=CC(OC)=CC=C2C(C)=C1C(CCCC)CCSC1=NC(CC(O)=O)=CS1 VGXJHTHNYSRSHN-UHFFFAOYSA-N 0.000 claims 1
- FXJJDFJCUSKROR-UHFFFAOYSA-N 2-[2-[3-[3-methyl-6-(trifluoromethyl)-1-benzothiophen-2-yl]heptylsulfanyl]-1,3-thiazol-4-yl]acetic acid Chemical compound S1C2=CC(C(F)(F)F)=CC=C2C(C)=C1C(CCCC)CCSC1=NC(CC(O)=O)=CS1 FXJJDFJCUSKROR-UHFFFAOYSA-N 0.000 claims 1
- VOWULFOXILZTAV-UHFFFAOYSA-N 2-[2-[5-methoxy-3-[3-methyl-6-(trifluoromethyl)-1-benzothiophen-2-yl]pentyl]sulfanyl-4-methyl-1,3-thiazol-5-yl]acetic acid Chemical compound S1C2=CC(C(F)(F)F)=CC=C2C(C)=C1C(CCOC)CCSC1=NC(C)=C(CC(O)=O)S1 VOWULFOXILZTAV-UHFFFAOYSA-N 0.000 claims 1
- AUSOXBAQFBKANU-UHFFFAOYSA-N 2-[2-ethyl-4-[3-[3-ethyl-6-(trifluoromethyl)-1-benzothiophen-2-yl]propylsulfanyl]phenoxy]acetic acid Chemical compound S1C2=CC(C(F)(F)F)=CC=C2C(CC)=C1CCCSC1=CC=C(OCC(O)=O)C(CC)=C1 AUSOXBAQFBKANU-UHFFFAOYSA-N 0.000 claims 1
- NUBYEMQTGIPNOH-UHFFFAOYSA-N 2-[2-ethyl-4-[3-[3-methyl-5-(trifluoromethyl)-1-benzothiophen-2-yl]propylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(CC)=CC(SCCCC2=C(C3=CC(=CC=C3S2)C(F)(F)F)C)=C1 NUBYEMQTGIPNOH-UHFFFAOYSA-N 0.000 claims 1
- OJVUVIXYAHGQPV-UHFFFAOYSA-N 2-[2-ethyl-4-[3-[3-methyl-6-(trifluoromethyl)-1-benzothiophen-2-yl]heptoxy]phenoxy]acetic acid Chemical compound S1C2=CC(C(F)(F)F)=CC=C2C(C)=C1C(CCCC)CCOC1=CC=C(OCC(O)=O)C(CC)=C1 OJVUVIXYAHGQPV-UHFFFAOYSA-N 0.000 claims 1
- YYGXSXXJQJNXKQ-UHFFFAOYSA-N 2-[2-ethyl-4-[3-[3-methyl-6-(trifluoromethyl)-1-benzothiophen-2-yl]hexoxy]phenoxy]acetic acid Chemical compound S1C2=CC(C(F)(F)F)=CC=C2C(C)=C1C(CCC)CCOC1=CC=C(OCC(O)=O)C(CC)=C1 YYGXSXXJQJNXKQ-UHFFFAOYSA-N 0.000 claims 1
- DZNZTCUSFBLLSQ-UHFFFAOYSA-N 2-[2-ethyl-4-[3-[3-methyl-6-(trifluoromethyl)-1-benzothiophen-2-yl]propylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(CC)=CC(SCCCC2=C(C3=CC=C(C=C3S2)C(F)(F)F)C)=C1 DZNZTCUSFBLLSQ-UHFFFAOYSA-N 0.000 claims 1
- DFJCXQJTYVAQDE-UHFFFAOYSA-N 2-[2-ethyl-4-[3-[5-(trifluoromethyl)-1-benzothiophen-2-yl]heptoxy]phenoxy]acetic acid Chemical compound C=1C2=CC(C(F)(F)F)=CC=C2SC=1C(CCCC)CCOC1=CC=C(OCC(O)=O)C(CC)=C1 DFJCXQJTYVAQDE-UHFFFAOYSA-N 0.000 claims 1
- YUCAPDVZOIZTIO-UHFFFAOYSA-N 2-[2-ethyl-4-[3-[6-(trifluoromethyl)-1-benzothiophen-2-yl]propylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(CC)=CC(SCCCC=2SC3=CC(=CC=C3C=2)C(F)(F)F)=C1 YUCAPDVZOIZTIO-UHFFFAOYSA-N 0.000 claims 1
- VYGAYXVFXNMYAS-UHFFFAOYSA-N 2-[2-ethyl-4-[5-methoxy-3-[3-methyl-6-(trifluoromethyl)-1-benzothiophen-2-yl]pentoxy]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(CC)=CC(OCCC(CCOC)C2=C(C3=CC=C(C=C3S2)C(F)(F)F)C)=C1 VYGAYXVFXNMYAS-UHFFFAOYSA-N 0.000 claims 1
- GMKXJFUYVOVIJS-ONEGZZNKSA-N 2-[2-methyl-4-[(e)-3-[3-methyl-5-(trifluoromethyl)-1-benzothiophen-2-yl]prop-2-enyl]sulfanylphenoxy]acetic acid Chemical compound S1C2=CC=C(C(F)(F)F)C=C2C(C)=C1\C=C\CSC1=CC=C(OCC(O)=O)C(C)=C1 GMKXJFUYVOVIJS-ONEGZZNKSA-N 0.000 claims 1
- JERJVQFCGWSTMH-UHFFFAOYSA-N 2-[2-methyl-4-[3-[3-methyl-5-(trifluoromethyl)-1-benzothiophen-2-yl]heptylsulfanyl]phenoxy]acetic acid Chemical compound S1C2=CC=C(C(F)(F)F)C=C2C(C)=C1C(CCCC)CCSC1=CC=C(OCC(O)=O)C(C)=C1 JERJVQFCGWSTMH-UHFFFAOYSA-N 0.000 claims 1
- HEWDOJXIUNGZRD-UHFFFAOYSA-N 2-[2-methyl-4-[3-[3-methyl-5-(trifluoromethyl)-1-benzothiophen-2-yl]propylsulfanyl]phenoxy]acetic acid Chemical compound S1C2=CC=C(C(F)(F)F)C=C2C(C)=C1CCCSC1=CC=C(OCC(O)=O)C(C)=C1 HEWDOJXIUNGZRD-UHFFFAOYSA-N 0.000 claims 1
- OMDUQLMNEWOCDA-UHFFFAOYSA-N 2-[2-methyl-4-[3-[3-methyl-6-(trifluoromethyl)-1-benzofuran-2-yl]heptoxy]phenoxy]acetic acid Chemical compound O1C2=CC(C(F)(F)F)=CC=C2C(C)=C1C(CCCC)CCOC1=CC=C(OCC(O)=O)C(C)=C1 OMDUQLMNEWOCDA-UHFFFAOYSA-N 0.000 claims 1
- NFTFENDUJTZGLE-UHFFFAOYSA-N 2-[2-methyl-4-[3-[3-methyl-6-(trifluoromethyl)-1-benzofuran-2-yl]heptylsulfanyl]phenoxy]acetic acid Chemical compound O1C2=CC(C(F)(F)F)=CC=C2C(C)=C1C(CCCC)CCSC1=CC=C(OCC(O)=O)C(C)=C1 NFTFENDUJTZGLE-UHFFFAOYSA-N 0.000 claims 1
- POPBXZUTOLKDDX-UHFFFAOYSA-N 2-[2-methyl-4-[3-[3-methyl-6-(trifluoromethyl)-1-benzothiophen-2-yl]-3-propoxypropoxy]phenoxy]acetic acid Chemical compound S1C2=CC(C(F)(F)F)=CC=C2C(C)=C1C(OCCC)CCOC1=CC=C(OCC(O)=O)C(C)=C1 POPBXZUTOLKDDX-UHFFFAOYSA-N 0.000 claims 1
- ZRROAQMJVLVQBL-UHFFFAOYSA-N 2-[2-methyl-4-[3-[3-methyl-6-(trifluoromethyl)-1-benzothiophen-2-yl]-3-propoxypropyl]sulfanylphenoxy]acetic acid Chemical compound S1C2=CC(C(F)(F)F)=CC=C2C(C)=C1C(OCCC)CCSC1=CC=C(OCC(O)=O)C(C)=C1 ZRROAQMJVLVQBL-UHFFFAOYSA-N 0.000 claims 1
- OEVMGZTXXMKIRO-UHFFFAOYSA-N 2-[2-methyl-4-[3-[3-methyl-6-(trifluoromethyl)-1-benzothiophen-2-yl]heptoxy]phenoxy]acetic acid Chemical compound S1C2=CC(C(F)(F)F)=CC=C2C(C)=C1C(CCCC)CCOC1=CC=C(OCC(O)=O)C(C)=C1 OEVMGZTXXMKIRO-UHFFFAOYSA-N 0.000 claims 1
- IYEZGOGEQUYVGH-UHFFFAOYSA-N 2-[2-methyl-4-[3-[3-methyl-6-(trifluoromethyl)-1-benzothiophen-2-yl]heptylsulfanyl]phenoxy]acetic acid Chemical compound S1C2=CC(C(F)(F)F)=CC=C2C(C)=C1C(CCCC)CCSC1=CC=C(OCC(O)=O)C(C)=C1 IYEZGOGEQUYVGH-UHFFFAOYSA-N 0.000 claims 1
- XUFQWLWCCYYKAM-UHFFFAOYSA-N 2-[2-methyl-4-[3-[3-methyl-6-(trifluoromethyl)-1-benzothiophen-2-yl]hexoxy]phenoxy]acetic acid Chemical compound S1C2=CC(C(F)(F)F)=CC=C2C(C)=C1C(CCC)CCOC1=CC=C(OCC(O)=O)C(C)=C1 XUFQWLWCCYYKAM-UHFFFAOYSA-N 0.000 claims 1
- QPQNULSDWKKYAM-UHFFFAOYSA-N 2-[2-methyl-4-[3-[3-methyl-6-(trifluoromethyl)-1-benzothiophen-2-yl]hexylsulfanyl]phenoxy]acetic acid Chemical compound S1C2=CC(C(F)(F)F)=CC=C2C(C)=C1C(CCC)CCSC1=CC=C(OCC(O)=O)C(C)=C1 QPQNULSDWKKYAM-UHFFFAOYSA-N 0.000 claims 1
- RZEFLUHNSFPPIH-UHFFFAOYSA-N 2-[2-methyl-4-[3-[5-(trifluoromethyl)-1-benzothiophen-2-yl]heptoxy]phenoxy]acetic acid Chemical compound C=1C2=CC(C(F)(F)F)=CC=C2SC=1C(CCCC)CCOC1=CC=C(OCC(O)=O)C(C)=C1 RZEFLUHNSFPPIH-UHFFFAOYSA-N 0.000 claims 1
- OSEBYFMDZGWTQN-UHFFFAOYSA-N 2-[2-methyl-4-[3-[5-(trifluoromethyl)-1-benzothiophen-2-yl]heptylsulfanyl]phenoxy]acetic acid Chemical compound C=1C2=CC(C(F)(F)F)=CC=C2SC=1C(CCCC)CCSC1=CC=C(OCC(O)=O)C(C)=C1 OSEBYFMDZGWTQN-UHFFFAOYSA-N 0.000 claims 1
- ZNNFMQMFSKGLKH-UHFFFAOYSA-N 2-[2-methyl-4-[3-[6-(trifluoromethyl)-1-benzothiophen-2-yl]heptylsulfanyl]phenoxy]acetic acid Chemical compound C=1C2=CC=C(C(F)(F)F)C=C2SC=1C(CCCC)CCSC1=CC=C(OCC(O)=O)C(C)=C1 ZNNFMQMFSKGLKH-UHFFFAOYSA-N 0.000 claims 1
- YFBWSQVLWVDVAI-UHFFFAOYSA-N 2-[2-methyl-4-[3-[6-(trifluoromethyl)-1-benzothiophen-2-yl]propylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(SCCCC=2SC3=CC(=CC=C3C=2)C(F)(F)F)=C1 YFBWSQVLWVDVAI-UHFFFAOYSA-N 0.000 claims 1
- HDIYLWYUCPDJDY-UHFFFAOYSA-N 2-[3-chloro-4-[3-[3-methyl-6-(trifluoromethyl)-1-benzothiophen-2-yl]heptoxy]phenyl]acetic acid Chemical compound S1C2=CC(C(F)(F)F)=CC=C2C(C)=C1C(CCCC)CCOC1=CC=C(CC(O)=O)C=C1Cl HDIYLWYUCPDJDY-UHFFFAOYSA-N 0.000 claims 1
- XCHRMFXHHRIWKD-UHFFFAOYSA-N 2-[3-methoxy-4-[3-(6-methoxy-3-methyl-1-benzothiophen-2-yl)heptoxy]phenyl]acetic acid Chemical compound S1C2=CC(OC)=CC=C2C(C)=C1C(CCCC)CCOC1=CC=C(CC(O)=O)C=C1OC XCHRMFXHHRIWKD-UHFFFAOYSA-N 0.000 claims 1
- ZNMQOXPLRKBIES-UHFFFAOYSA-N 2-[3-methoxy-4-[3-[3-methyl-6-(trifluoromethyl)-1-benzothiophen-2-yl]heptoxy]phenyl]acetic acid Chemical compound S1C2=CC(C(F)(F)F)=CC=C2C(C)=C1C(CCCC)CCOC1=CC=C(CC(O)=O)C=C1OC ZNMQOXPLRKBIES-UHFFFAOYSA-N 0.000 claims 1
- RXMKASBTNBTGGN-UHFFFAOYSA-N 2-[4-[3-(3,6-dimethyl-1-benzofuran-2-yl)heptoxy]-2-methylphenoxy]acetic acid Chemical compound O1C2=CC(C)=CC=C2C(C)=C1C(CCCC)CCOC1=CC=C(OCC(O)=O)C(C)=C1 RXMKASBTNBTGGN-UHFFFAOYSA-N 0.000 claims 1
- VIJPVPMCLKQJMY-UHFFFAOYSA-N 2-[4-[3-(3,6-dimethyl-1-benzofuran-2-yl)heptylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound O1C2=CC(C)=CC=C2C(C)=C1C(CCCC)CCSC1=CC=C(OCC(O)=O)C(C)=C1 VIJPVPMCLKQJMY-UHFFFAOYSA-N 0.000 claims 1
- XGGUGNHNYYURFC-UHFFFAOYSA-N 2-[4-[3-(5-bromo-3-methyl-1-benzothiophen-2-yl)propylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound S1C2=CC=C(Br)C=C2C(C)=C1CCCSC1=CC=C(OCC(O)=O)C(C)=C1 XGGUGNHNYYURFC-UHFFFAOYSA-N 0.000 claims 1
- QKVXJSLRWANCGT-UHFFFAOYSA-N 2-[4-[3-(5-fluoro-3-methyl-1-benzothiophen-2-yl)heptoxy]-2-methylphenoxy]acetic acid Chemical compound S1C2=CC=C(F)C=C2C(C)=C1C(CCCC)CCOC1=CC=C(OCC(O)=O)C(C)=C1 QKVXJSLRWANCGT-UHFFFAOYSA-N 0.000 claims 1
- AZAKALCUEVRNDX-UHFFFAOYSA-N 2-[4-[3-(6-bromo-3-methyl-1-benzothiophen-2-yl)propoxy]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound S1C2=CC(Br)=CC=C2C(C)=C1CCCOC1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 AZAKALCUEVRNDX-UHFFFAOYSA-N 0.000 claims 1
- PEPWPAKMSHIYKY-UHFFFAOYSA-N 2-[4-[3-(6-bromo-3-methyl-1-benzothiophen-2-yl)propylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound S1C2=CC(Br)=CC=C2C(C)=C1CCCSC1=CC=C(OCC(O)=O)C(C)=C1 PEPWPAKMSHIYKY-UHFFFAOYSA-N 0.000 claims 1
- AICUJBWVKWNGFS-UHFFFAOYSA-N 2-[4-[3-(6-fluoro-1-benzothiophen-2-yl)heptoxy]-2-methylphenoxy]acetic acid Chemical compound C=1C2=CC=C(F)C=C2SC=1C(CCCC)CCOC1=CC=C(OCC(O)=O)C(C)=C1 AICUJBWVKWNGFS-UHFFFAOYSA-N 0.000 claims 1
- ZCBJYMXDUWHPQA-UHFFFAOYSA-N 2-[4-[3-(6-fluoro-3-methyl-1-benzothiophen-2-yl)heptoxy]-2-methylphenoxy]acetic acid Chemical compound S1C2=CC(F)=CC=C2C(C)=C1C(CCCC)CCOC1=CC=C(OCC(O)=O)C(C)=C1 ZCBJYMXDUWHPQA-UHFFFAOYSA-N 0.000 claims 1
- FLDOOVATKOXQMV-UHFFFAOYSA-N 2-[4-[3-(6-fluoro-3-methyl-1-benzothiophen-2-yl)heptylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound S1C2=CC(F)=CC=C2C(C)=C1C(CCCC)CCSC1=CC=C(OCC(O)=O)C(C)=C1 FLDOOVATKOXQMV-UHFFFAOYSA-N 0.000 claims 1
- UGRIRRAVVNVIJK-UHFFFAOYSA-N 2-[4-[3-(6-methoxy-3-methyl-1-benzothiophen-2-yl)heptoxy]-2-methylphenoxy]acetic acid Chemical compound S1C2=CC(OC)=CC=C2C(C)=C1C(CCCC)CCOC1=CC=C(OCC(O)=O)C(C)=C1 UGRIRRAVVNVIJK-UHFFFAOYSA-N 0.000 claims 1
- YZVSXGYNRHQZAZ-UHFFFAOYSA-N 2-[4-[3-[3-ethyl-5-(trifluoromethyl)-1-benzothiophen-2-yl]heptoxy]-2-methylphenoxy]acetic acid Chemical compound S1C2=CC=C(C(F)(F)F)C=C2C(CC)=C1C(CCCC)CCOC1=CC=C(OCC(O)=O)C(C)=C1 YZVSXGYNRHQZAZ-UHFFFAOYSA-N 0.000 claims 1
- YQULHHOIJRHBSQ-UHFFFAOYSA-N 2-[4-[3-[3-ethyl-6-(trifluoromethyl)-1-benzothiophen-2-yl]propylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound S1C2=CC(C(F)(F)F)=CC=C2C(CC)=C1CCCSC1=CC=C(OCC(O)=O)C(C)=C1 YQULHHOIJRHBSQ-UHFFFAOYSA-N 0.000 claims 1
- UIZGMDMTDDLUPV-UHFFFAOYSA-N 2-[4-[3-[3-methyl-6-(trifluoromethyl)-1-benzothiophen-2-yl]heptoxy]phenyl]acetic acid Chemical compound S1C2=CC(C(F)(F)F)=CC=C2C(C)=C1C(CCCC)CCOC1=CC=C(CC(O)=O)C=C1 UIZGMDMTDDLUPV-UHFFFAOYSA-N 0.000 claims 1
- LPNTUHKHJYRYCM-UHFFFAOYSA-N 2-[4-[3-[3-methyl-6-(trifluoromethyl)-1-benzothiophen-2-yl]propylsulfanyl]-2-(trifluoromethyl)phenoxy]acetic acid Chemical compound S1C2=CC(C(F)(F)F)=CC=C2C(C)=C1CCCSC1=CC=C(OCC(O)=O)C(C(F)(F)F)=C1 LPNTUHKHJYRYCM-UHFFFAOYSA-N 0.000 claims 1
- IOJUPKZESHJIMF-UHFFFAOYSA-N 2-[4-[5-methoxy-3-[3-methyl-6-(trifluoromethyl)-1-benzothiophen-2-yl]pentoxy]-2-methylphenoxy]acetic acid Chemical compound S1C2=CC(C(F)(F)F)=CC=C2C(C)=C1C(CCOC)CCOC1=CC=C(OCC(O)=O)C(C)=C1 IOJUPKZESHJIMF-UHFFFAOYSA-N 0.000 claims 1
- AWMNUQGDRDMGNG-UHFFFAOYSA-N 2-[4-[5-methoxy-3-[3-methyl-6-(trifluoromethyl)-1-benzothiophen-2-yl]pentyl]sulfanyl-2-methylphenoxy]acetic acid Chemical compound S1C2=CC(C(F)(F)F)=CC=C2C(C)=C1C(CCOC)CCSC1=CC=C(OCC(O)=O)C(C)=C1 AWMNUQGDRDMGNG-UHFFFAOYSA-N 0.000 claims 1
- NIVUSNITPYAXDD-UHFFFAOYSA-N 2-[4-methyl-2-[3-[3-methyl-6-(trifluoromethyl)-1-benzofuran-2-yl]heptylsulfanyl]-1,3-thiazol-5-yl]acetic acid Chemical compound O1C2=CC(C(F)(F)F)=CC=C2C(C)=C1C(CCCC)CCSC1=NC(C)=C(CC(O)=O)S1 NIVUSNITPYAXDD-UHFFFAOYSA-N 0.000 claims 1
- HQBOQKZRRLZKPO-UHFFFAOYSA-N 2-[4-methyl-2-[3-[3-methyl-6-(trifluoromethyl)-1-benzothiophen-2-yl]heptylsulfanyl]-1,3-thiazol-5-yl]acetic acid Chemical compound S1C2=CC(C(F)(F)F)=CC=C2C(C)=C1C(CCCC)CCSC1=NC(C)=C(CC(O)=O)S1 HQBOQKZRRLZKPO-UHFFFAOYSA-N 0.000 claims 1
- KBQXDCQBSNHIBG-UHFFFAOYSA-N 2-[4-methyl-2-[3-[3-methyl-6-(trifluoromethyl)-1-benzothiophen-2-yl]hexylsulfanyl]-1,3-thiazol-5-yl]acetic acid Chemical compound S1C2=CC(C(F)(F)F)=CC=C2C(C)=C1C(CCC)CCSC1=NC(C)=C(CC(O)=O)S1 KBQXDCQBSNHIBG-UHFFFAOYSA-N 0.000 claims 1
- UVOVHRPTMQWDGV-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[3-[3-methyl-5-(trifluoromethyl)-1-benzothiophen-2-yl]propoxy]phenoxy]propanoic acid Chemical compound S1C2=CC=C(C(F)(F)F)C=C2C(C)=C1CCCOC1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 UVOVHRPTMQWDGV-UHFFFAOYSA-N 0.000 claims 1
- WQOCGSFXMKPGQF-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[3-[3-methyl-6-(trifluoromethyl)-1-benzothiophen-2-yl]propoxy]phenoxy]propanoic acid Chemical compound S1C2=CC(C(F)(F)F)=CC=C2C(C)=C1CCCOC1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 WQOCGSFXMKPGQF-UHFFFAOYSA-N 0.000 claims 1
- SOTMPMXBOUSVEC-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[3-[3-methyl-6-(trifluoromethyl)-1-benzothiophen-2-yl]propylsulfanyl]phenoxy]propanoic acid Chemical compound S1C2=CC(C(F)(F)F)=CC=C2C(C)=C1CCCSC1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 SOTMPMXBOUSVEC-UHFFFAOYSA-N 0.000 claims 1
- YLWDHISOLHDLNW-UHFFFAOYSA-N 3-[3-methoxy-4-[3-[3-methyl-6-(trifluoromethyl)-1-benzothiophen-2-yl]heptoxy]phenyl]propanoic acid Chemical compound S1C2=CC(C(F)(F)F)=CC=C2C(C)=C1C(CCCC)CCOC1=CC=C(CCC(O)=O)C=C1OC YLWDHISOLHDLNW-UHFFFAOYSA-N 0.000 claims 1
- IRZOSBKFGJKJDZ-UHFFFAOYSA-N 3-[4-[3-[3-methyl-6-(trifluoromethyl)-1-benzothiophen-2-yl]heptoxy]phenyl]propanoic acid Chemical compound S1C2=CC(C(F)(F)F)=CC=C2C(C)=C1C(CCCC)CCOC1=CC=C(CCC(O)=O)C=C1 IRZOSBKFGJKJDZ-UHFFFAOYSA-N 0.000 claims 1
- 208000000103 Anorexia Nervosa Diseases 0.000 claims 1
- 206010006550 Bulimia nervosa Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000032928 Dyslipidaemia Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 1
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 1
- 206010022489 Insulin Resistance Diseases 0.000 claims 1
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 1
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- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
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| GBGB0403148.0A GB0403148D0 (en) | 2004-02-12 | 2004-02-12 | Chemical compounds |
| PCT/EP2005/001540 WO2005077926A2 (en) | 2004-02-12 | 2005-02-10 | Benzofuran and benzothiophene derivatives useful for the treatment of cardiovascular disease |
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| JP2007522178A JP2007522178A (ja) | 2007-08-09 |
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| EP (1) | EP1740568B1 (https=) |
| JP (1) | JP2007522178A (https=) |
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| ES (1) | ES2317192T3 (https=) |
| GB (1) | GB0403148D0 (https=) |
| WO (1) | WO2005077926A2 (https=) |
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| CN1980891B (zh) * | 2004-05-03 | 2011-03-09 | 詹森药业有限公司 | 作为选择性雄激素受体调节剂(sarms)的吲哚、苯并呋喃和苯并噻吩衍生物 |
| TWI359810B (en) * | 2004-11-04 | 2012-03-11 | Mitsubishi Tanabe Pharma Corp | Carboxylic acid derivative containing thiazole rin |
| WO2006101454A1 (en) * | 2005-03-21 | 2006-09-28 | S*Bio Pte Ltd | Benzothiophene derivatives: preparation and pharmaceutical applications |
| CN101466687B (zh) | 2006-04-18 | 2012-04-11 | 日本化学医药株式会社 | 过氧化物酶体增殖剂激活受体δ的激活剂 |
| AU2008338963A1 (en) * | 2007-12-13 | 2009-06-25 | Sri International | PPAR-delta ligands and methods of their use |
| EP2277874B1 (en) * | 2008-04-15 | 2018-06-27 | Nippon Chemiphar Co., Ltd. | Activator for peroxisome proliferator-activated receptor |
| CN102724978A (zh) * | 2009-08-14 | 2012-10-10 | 塞伦尼斯治疗公司 | 用于治疗或预防炎症或能量代谢/产生相关疾病的PPARδ配体的用途 |
| JP5929483B2 (ja) * | 2011-05-10 | 2016-06-08 | 住友化学株式会社 | 植物の生長を促進する方法 |
| JP5929482B2 (ja) * | 2011-05-10 | 2016-06-08 | 住友化学株式会社 | 植物の生長を促進する方法 |
| CN111393405B (zh) * | 2019-01-02 | 2022-11-25 | 中国科学院上海药物研究所 | 一类含氟取代的苯并噻吩类化合物及其药物组合物及应用 |
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| US5859051A (en) * | 1996-02-02 | 1999-01-12 | Merck & Co., Inc. | Antidiabetic agents |
| WO1997028149A1 (en) * | 1996-02-02 | 1997-08-07 | Merck & Co., Inc. | Method for raising hdl cholesterol levels |
| ATE293963T1 (de) * | 1996-02-02 | 2005-05-15 | Merck & Co Inc | Verfahren zur behandlung von diabetes und verwandter krankheitszustände. |
| EP0948327B1 (en) * | 1996-12-23 | 2006-03-08 | Merck & Co., Inc. | Antidiabetic agents |
| MXPA02007286A (es) * | 2000-01-28 | 2002-11-29 | Novo Nordisk As | Derivados de acido propionico y su uso en el tratamiento de diabetes y obesidad. |
| JP2001261674A (ja) * | 2000-03-22 | 2001-09-26 | Mitsui Chemicals Inc | ベンゾチオフェン誘導体およびそれを有効成分として含有する核内レセプター作動薬 |
| GB0111523D0 (en) * | 2001-05-11 | 2001-07-04 | Glaxo Group Ltd | Chemical compounds |
| US6875780B2 (en) * | 2002-04-05 | 2005-04-05 | Warner-Lambert Company | Compounds that modulate PPAR activity and methods for their preparation |
| JP4475406B2 (ja) * | 2002-07-30 | 2010-06-09 | メルク・シャープ・エンド・ドーム・コーポレイション | 異常脂血症および他の脂質障害の治療用のＰＰＡＲα選択的化合物 |
| DE60332860D1 (de) * | 2002-10-28 | 2010-07-15 | High Point Pharmaceuticals Llc | Neue verbindungen, die sich f r die behandlung von durch ppar vermittelten krankheiten eignen |
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2004
- 2004-02-12 GB GBGB0403148.0A patent/GB0403148D0/en not_active Ceased
-
2005
- 2005-02-10 WO PCT/EP2005/001540 patent/WO2005077926A2/en not_active Ceased
- 2005-02-10 AT AT05707417T patent/ATE415395T1/de not_active IP Right Cessation
- 2005-02-10 ES ES05707417T patent/ES2317192T3/es not_active Expired - Lifetime
- 2005-02-10 DE DE602005011267T patent/DE602005011267D1/de not_active Expired - Fee Related
- 2005-02-10 EP EP05707417A patent/EP1740568B1/en not_active Expired - Lifetime
- 2005-02-10 US US10/597,870 patent/US20070155805A1/en not_active Abandoned
- 2005-02-10 JP JP2006552575A patent/JP2007522178A/ja active Pending