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
- 208000008589 Obesity Diseases 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Applications Claiming Priority (2)
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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 |
Publications (2)
| Publication Number | Publication Date |
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| JP2007522178A JP2007522178A (ja) | 2007-08-09 |
| JP2007522178A5 true JP2007522178A5 (https=) | 2007-11-15 |
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| JP2006552575A Pending JP2007522178A (ja) | 2004-02-12 | 2005-02-10 | 心臓血管疾患の治療に有用なベンゾフランおよびベンゾチオフェン誘導体 |
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| US (1) | US20070155805A1 (https=) |
| EP (1) | EP1740568B1 (https=) |
| JP (1) | JP2007522178A (https=) |
| AT (1) | ATE415395T1 (https=) |
| DE (1) | DE602005011267D1 (https=) |
| ES (1) | ES2317192T3 (https=) |
| GB (1) | GB0403148D0 (https=) |
| WO (1) | WO2005077926A2 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US20090163481A1 (en) * | 2007-12-13 | 2009-06-25 | Murphy Brian J | Ppar-delta ligands and methods of their use |
| MX2010011252A (es) | 2008-04-15 | 2010-11-30 | Nippon Chemiphar Co | Activador para el receptor activado por el proliferador de peroxisoma. |
| AU2010282399A1 (en) * | 2009-08-14 | 2012-03-01 | Cerenis Therapeutics Holding S.A. | Use of PPAR delta ligands for the treatment or prevention of inflammation or energy metabolism/production related diseases |
| 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 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU1856997A (en) * | 1996-02-02 | 1997-08-22 | Merck & Co., Inc. | Method for raising hdl cholesterol levels |
| US5859051A (en) * | 1996-02-02 | 1999-01-12 | Merck & Co., Inc. | Antidiabetic agents |
| EP1011651B1 (en) * | 1996-02-02 | 2005-04-27 | Merck & Co., Inc. | Method of treating diabetes and related disease states |
| WO1998027974A1 (en) * | 1996-12-23 | 1998-07-02 | Merck & Co., Inc. | Antidiabetic agents |
| AU2831901A (en) * | 2000-01-28 | 2001-08-07 | Novo Nordisk A/S | Propionic acid derivatives and their use in the treatment of diabetes and obesity |
| 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 |
| CA2491733A1 (en) * | 2002-07-30 | 2004-02-05 | Merck & Co., Inc. | Ppar alpha selective compounds for the treatment of dyslipidemia and other lipid disorders |
| JP4584714B2 (ja) * | 2002-10-28 | 2010-11-24 | ハイ・ポイント・ファーマスーティカルズ、エルエルシー | 新規化合物、その調製および使用 |
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2004
- 2004-02-12 GB GBGB0403148.0A patent/GB0403148D0/en not_active Ceased
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2005
- 2005-02-10 AT AT05707417T patent/ATE415395T1/de not_active IP Right Cessation
- 2005-02-10 WO PCT/EP2005/001540 patent/WO2005077926A2/en not_active Ceased
- 2005-02-10 JP JP2006552575A patent/JP2007522178A/ja active Pending
- 2005-02-10 EP EP05707417A patent/EP1740568B1/en not_active Expired - Lifetime
- 2005-02-10 DE DE602005011267T patent/DE602005011267D1/de not_active Expired - Fee Related
- 2005-02-10 ES ES05707417T patent/ES2317192T3/es not_active Expired - Lifetime
- 2005-02-10 US US10/597,870 patent/US20070155805A1/en not_active Abandoned
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