JP2005534673A5 - - Google Patents
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- JP2005534673A5 JP2005534673A5 JP2004514762A JP2004514762A JP2005534673A5 JP 2005534673 A5 JP2005534673 A5 JP 2005534673A5 JP 2004514762 A JP2004514762 A JP 2004514762A JP 2004514762 A JP2004514762 A JP 2004514762A JP 2005534673 A5 JP2005534673 A5 JP 2005534673A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- amino
- acetic acid
- methylphenoxy
- 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 16
- 125000000217 alkyl group Chemical group 0.000 claims 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- -1 methoxyethyl Chemical group 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- YGHHZEFCBIZSSB-UHFFFAOYSA-N 2-[2-methyl-4-[[n-propylsulfonyl-3-[4-(trifluoromethyl)phenyl]anilino]methyl]phenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=CC=1N(S(=O)(=O)CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 YGHHZEFCBIZSSB-UHFFFAOYSA-N 0.000 claims 2
- 208000000103 Anorexia Nervosa Diseases 0.000 claims 2
- 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
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- UVNNBABQBZZBNO-UHFFFAOYSA-N 2-[2-ethyl-4-[[2-methoxyethyl-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]amino]methyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(CC)=CC(CN(CCOC)C=2N=C(C=CN=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 UVNNBABQBZZBNO-UHFFFAOYSA-N 0.000 claims 1
- KNOPTCHXVXPURE-UHFFFAOYSA-N 2-[2-methyl-4-[[2-methyl-3-(4-methylphenyl)-n-propylanilino]methyl]phenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(C)=CC=2)=C(C)C=1N(CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 KNOPTCHXVXPURE-UHFFFAOYSA-N 0.000 claims 1
- GOPJHQJXIVHRQS-UHFFFAOYSA-N 2-[2-methyl-4-[[2-methyl-n-propyl-3-[4-(trifluoromethyl)phenyl]anilino]methyl]phenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=C(C)C=1N(CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 GOPJHQJXIVHRQS-UHFFFAOYSA-N 0.000 claims 1
- VDKVCJMUCCAMMG-UHFFFAOYSA-N 2-[2-methyl-4-[[[5-methyl-6-(4-methylphenyl)pyrimidin-4-yl]-propylamino]methyl]phenoxy]acetic acid Chemical compound N=1C=NC(C=2C=CC(C)=CC=2)=C(C)C=1N(CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 VDKVCJMUCCAMMG-UHFFFAOYSA-N 0.000 claims 1
- ZDYXOCIDDCFARL-UHFFFAOYSA-N 2-[2-methyl-4-[[[5-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-4-yl]-propylamino]methyl]phenoxy]acetic acid Chemical compound N=1C=NC(C=2C=CC(=CC=2)C(F)(F)F)=C(C)C=1N(CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 ZDYXOCIDDCFARL-UHFFFAOYSA-N 0.000 claims 1
- MJEXFSLFJSRENW-UHFFFAOYSA-N 2-[2-methyl-4-[[n-(2-methylsulfanylethyl)-3-[4-(trifluoromethyl)phenyl]anilino]methyl]phenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=CC=1N(CCSC)CC1=CC=C(OCC(O)=O)C(C)=C1 MJEXFSLFJSRENW-UHFFFAOYSA-N 0.000 claims 1
- PEAWRZYPKVFBPF-UHFFFAOYSA-N 2-[2-methyl-4-[[n-pentyl-3-[4-(trifluoromethyl)phenyl]anilino]methyl]phenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=CC=1N(CCCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 PEAWRZYPKVFBPF-UHFFFAOYSA-N 0.000 claims 1
- RRCPLRUPTKQMHM-UHFFFAOYSA-N 2-[2-methyl-4-[[n-propyl-3-[4-(trifluoromethyl)phenyl]anilino]methyl]phenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=CC=1N(CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 RRCPLRUPTKQMHM-UHFFFAOYSA-N 0.000 claims 1
- HRQANTBARMMGIA-UHFFFAOYSA-N 2-[2-methyl-4-[[prop-2-enyl-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]amino]methyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(CN(CC=C)C=2N=C(C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 HRQANTBARMMGIA-UHFFFAOYSA-N 0.000 claims 1
- XSJSAVYSMORDHC-UHFFFAOYSA-N 2-[2-methyl-4-[[propyl-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]amino]methyl]phenoxy]acetic acid Chemical compound N=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1N(CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 XSJSAVYSMORDHC-UHFFFAOYSA-N 0.000 claims 1
- PRKYXPRHKQIKBQ-UHFFFAOYSA-N 2-[2-methyl-4-[[propyl-[6-[4-(trifluoromethyl)phenyl]pyrazin-2-yl]amino]methyl]phenoxy]acetic acid Chemical compound C=1N=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1N(CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 PRKYXPRHKQIKBQ-UHFFFAOYSA-N 0.000 claims 1
- OGIZWBGYLHQGQE-UHFFFAOYSA-N 2-[2-methyl-4-[pentyl-[3-[4-(trifluoromethyl)phenyl]phenyl]sulfamoyl]phenoxy]acetic acid Chemical compound C=1C=C(OCC(O)=O)C(C)=CC=1S(=O)(=O)N(CCCCC)C(C=1)=CC=CC=1C1=CC=C(C(F)(F)F)C=C1 OGIZWBGYLHQGQE-UHFFFAOYSA-N 0.000 claims 1
- IJYQDIOFQBLRMI-UHFFFAOYSA-N 2-[4-[2-cyclopropylethyl-[3-[4-(trifluoromethyl)phenyl]phenyl]sulfamoyl]-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(S(=O)(=O)N(CCC2CC2)C=2C=C(C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 IJYQDIOFQBLRMI-UHFFFAOYSA-N 0.000 claims 1
- HBFDXJXPMJPDGU-UHFFFAOYSA-N 2-[4-[[2-methoxyethyl-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]amino]methyl]-2-methylphenoxy]acetic acid Chemical compound N=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1N(CCOC)CC1=CC=C(OCC(O)=O)C(C)=C1 HBFDXJXPMJPDGU-UHFFFAOYSA-N 0.000 claims 1
- KNOLRYLXOFIMIC-UHFFFAOYSA-N 2-[4-[[2-methoxyethyl-[6-[4-(trifluoromethyl)phenyl]pyrazin-2-yl]amino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1N=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1N(CCOC)CC1=CC=C(OCC(O)=O)C(C)=C1 KNOLRYLXOFIMIC-UHFFFAOYSA-N 0.000 claims 1
- GJJIZDVLTCBHKV-UHFFFAOYSA-N 2-[4-[[3-(4-chlorophenyl)-2-methyl-n-propylanilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(Cl)=CC=2)=C(C)C=1N(CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 GJJIZDVLTCBHKV-UHFFFAOYSA-N 0.000 claims 1
- WLPNPIDPJYCYBO-UHFFFAOYSA-N 2-[4-[[3-(4-chlorophenyl)-n-(2-methoxyethyl)-2-methylanilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(Cl)=CC=2)=C(C)C=1N(CCOC)CC1=CC=C(OCC(O)=O)C(C)=C1 WLPNPIDPJYCYBO-UHFFFAOYSA-N 0.000 claims 1
- VENARYATHGDLAJ-UHFFFAOYSA-N 2-[4-[[3-(4-cyanophenyl)-2-methyl-n-propylanilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C#N)=C(C)C=1N(CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 VENARYATHGDLAJ-UHFFFAOYSA-N 0.000 claims 1
- PGEUUOYZXAXZAZ-UHFFFAOYSA-N 2-[4-[[3-(4-fluorophenyl)-2-methyl-n-propylanilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(F)=CC=2)=C(C)C=1N(CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 PGEUUOYZXAXZAZ-UHFFFAOYSA-N 0.000 claims 1
- MUMOEDHFUPBHAZ-UHFFFAOYSA-N 2-[4-[[3-(4-methoxyphenyl)-2-methyl-n-propylanilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(OC)=CC=2)=C(C)C=1N(CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 MUMOEDHFUPBHAZ-UHFFFAOYSA-N 0.000 claims 1
- YSMHQYZKUOJMKJ-UHFFFAOYSA-N 2-[4-[[[4-(4-chlorophenyl)pyrimidin-2-yl]-(2-methoxyethyl)amino]methyl]-2-methylphenoxy]acetic acid Chemical compound N=1C=CC(C=2C=CC(Cl)=CC=2)=NC=1N(CCOC)CC1=CC=C(OCC(O)=O)C(C)=C1 YSMHQYZKUOJMKJ-UHFFFAOYSA-N 0.000 claims 1
- MXNYXSHIAHNYNW-UHFFFAOYSA-N 2-[4-[[[6-(4-chlorophenyl)-5-methylpyrimidin-4-yl]-propylamino]methyl]-2-methylphenoxy]acetic acid Chemical compound N=1C=NC(C=2C=CC(Cl)=CC=2)=C(C)C=1N(CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 MXNYXSHIAHNYNW-UHFFFAOYSA-N 0.000 claims 1
- YMCNXXXIEVJJAB-UHFFFAOYSA-N 2-[4-[[[6-(4-chlorophenyl)pyrazin-2-yl]-(2-methoxyethyl)amino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1N=CC(C=2C=CC(Cl)=CC=2)=NC=1N(CCOC)CC1=CC=C(OCC(O)=O)C(C)=C1 YMCNXXXIEVJJAB-UHFFFAOYSA-N 0.000 claims 1
- KGCILICKONKQJI-UHFFFAOYSA-N 2-[4-[[[6-(4-methoxyphenyl)-5-methylpyrimidin-4-yl]-propylamino]methyl]-2-methylphenoxy]acetic acid Chemical compound N=1C=NC(C=2C=CC(OC)=CC=2)=C(C)C=1N(CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 KGCILICKONKQJI-UHFFFAOYSA-N 0.000 claims 1
- HKXPKBPNHDYJCY-UHFFFAOYSA-N 2-[4-[[butyl-[4-(4-chlorophenyl)pyrimidin-2-yl]amino]methyl]-2-methylphenoxy]acetic acid Chemical compound N=1C=CC(C=2C=CC(Cl)=CC=2)=NC=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 HKXPKBPNHDYJCY-UHFFFAOYSA-N 0.000 claims 1
- QURKGEHGLGJPRN-UHFFFAOYSA-N 2-[4-[[butyl-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]amino]methyl]-2-methylphenoxy]acetic acid Chemical compound N=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 QURKGEHGLGJPRN-UHFFFAOYSA-N 0.000 claims 1
- HPOJZOUKBUUIFU-UHFFFAOYSA-N 2-[4-[[butyl-[5-methyl-6-(4-methylphenyl)pyrimidin-4-yl]amino]methyl]-2-ethylphenoxy]acetic acid Chemical compound N=1C=NC(C=2C=CC(C)=CC=2)=C(C)C=1N(CCCC)CC1=CC=C(OCC(O)=O)C(CC)=C1 HPOJZOUKBUUIFU-UHFFFAOYSA-N 0.000 claims 1
- KJJUOYZUPWKUFR-UHFFFAOYSA-N 2-[4-[[butyl-[5-methyl-6-(4-methylphenyl)pyrimidin-4-yl]amino]methyl]-2-methylphenoxy]acetic acid Chemical compound N=1C=NC(C=2C=CC(C)=CC=2)=C(C)C=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 KJJUOYZUPWKUFR-UHFFFAOYSA-N 0.000 claims 1
- ZGSKFRBNMTYPHR-UHFFFAOYSA-N 2-[4-[[butyl-[5-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-4-yl]amino]methyl]-2-ethylphenoxy]acetic acid Chemical compound N=1C=NC(C=2C=CC(=CC=2)C(F)(F)F)=C(C)C=1N(CCCC)CC1=CC=C(OCC(O)=O)C(CC)=C1 ZGSKFRBNMTYPHR-UHFFFAOYSA-N 0.000 claims 1
- MPYIHZGPRROZIR-UHFFFAOYSA-N 2-[4-[[butyl-[5-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-4-yl]amino]methyl]-2-methylphenoxy]acetic acid Chemical compound N=1C=NC(C=2C=CC(=CC=2)C(F)(F)F)=C(C)C=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 MPYIHZGPRROZIR-UHFFFAOYSA-N 0.000 claims 1
- SBAZZTXQGDFQLR-UHFFFAOYSA-N 2-[4-[[butyl-[6-(4-chlorophenyl)-5-methylpyrimidin-4-yl]amino]methyl]-2-ethylphenoxy]acetic acid Chemical compound N=1C=NC(C=2C=CC(Cl)=CC=2)=C(C)C=1N(CCCC)CC1=CC=C(OCC(O)=O)C(CC)=C1 SBAZZTXQGDFQLR-UHFFFAOYSA-N 0.000 claims 1
- YURCSFYCXRYRBB-UHFFFAOYSA-N 2-[4-[[butyl-[6-(4-chlorophenyl)-5-methylpyrimidin-4-yl]amino]methyl]-2-methylphenoxy]acetic acid Chemical compound N=1C=NC(C=2C=CC(Cl)=CC=2)=C(C)C=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 YURCSFYCXRYRBB-UHFFFAOYSA-N 0.000 claims 1
- FBZXXHOWTFOFRV-UHFFFAOYSA-N 2-[4-[[butyl-[6-(4-methoxyphenyl)-5-methylpyrimidin-4-yl]amino]methyl]-2-methylphenoxy]acetic acid Chemical compound N=1C=NC(C=2C=CC(OC)=CC=2)=C(C)C=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 FBZXXHOWTFOFRV-UHFFFAOYSA-N 0.000 claims 1
- ASRAFPYPVQCHCA-UHFFFAOYSA-N 2-[4-[[butyl-[6-(4-methylphenyl)pyrazin-2-yl]amino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1N=CC(C=2C=CC(C)=CC=2)=NC=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 ASRAFPYPVQCHCA-UHFFFAOYSA-N 0.000 claims 1
- MENHQMYKCSUBHI-UHFFFAOYSA-N 2-[4-[[butyl-[6-[4-(trifluoromethyl)phenyl]pyrazin-2-yl]amino]methyl]-2-ethylphenoxy]acetic acid Chemical compound C=1N=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1N(CCCC)CC1=CC=C(OCC(O)=O)C(CC)=C1 MENHQMYKCSUBHI-UHFFFAOYSA-N 0.000 claims 1
- SBOOXZMRYAEKJJ-UHFFFAOYSA-N 2-[4-[[butyl-[6-[4-(trifluoromethyl)phenyl]pyrazin-2-yl]amino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1N=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 SBOOXZMRYAEKJJ-UHFFFAOYSA-N 0.000 claims 1
- IJHBSKLFWNWLAT-UHFFFAOYSA-N 2-[4-[[butyl-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]amino]methyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1N(CCCC)CC1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 IJHBSKLFWNWLAT-UHFFFAOYSA-N 0.000 claims 1
- CBCQOWIYROCGPP-UHFFFAOYSA-N 2-[4-[[butyl-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]amino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=NC=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 CBCQOWIYROCGPP-UHFFFAOYSA-N 0.000 claims 1
- LNIZHEWUDRFHHK-UHFFFAOYSA-N 2-[4-[[n-(2-cyclopropylethyl)-3-[4-(trifluoromethyl)phenyl]anilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(CN(CCC2CC2)C=2C=C(C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 LNIZHEWUDRFHHK-UHFFFAOYSA-N 0.000 claims 1
- XQADWKSWAZXWCW-UHFFFAOYSA-N 2-[4-[[n-(2-methoxyethyl)-2-methyl-3-(4-methylphenyl)anilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(C)=CC=2)=C(C)C=1N(CCOC)CC1=CC=C(OCC(O)=O)C(C)=C1 XQADWKSWAZXWCW-UHFFFAOYSA-N 0.000 claims 1
- VAYOMOVBKJCJNQ-UHFFFAOYSA-N 2-[4-[[n-(2-methoxyethyl)-2-methyl-3-[4-(trifluoromethyl)phenyl]anilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=C(C)C=1N(CCOC)CC1=CC=C(OCC(O)=O)C(C)=C1 VAYOMOVBKJCJNQ-UHFFFAOYSA-N 0.000 claims 1
- UGSMMDAQHBSSAD-UHFFFAOYSA-N 2-[4-[[n-(2-methoxyethyl)-3-[4-(trifluoromethyl)phenyl]anilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=CC=1N(CCOC)CC1=CC=C(OCC(O)=O)C(C)=C1 UGSMMDAQHBSSAD-UHFFFAOYSA-N 0.000 claims 1
- LRGPFBCSWCOXRN-UHFFFAOYSA-N 2-[4-[[n-butanoyl-3-[4-(trifluoromethyl)phenyl]anilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=CC=1N(C(=O)CCC)CC1=CC=C(OCC(O)=O)C(C)=C1 LRGPFBCSWCOXRN-UHFFFAOYSA-N 0.000 claims 1
- IADOHFNPFBVSGF-UHFFFAOYSA-N 2-[4-[[n-butyl-2-methyl-3-(4-methylphenyl)anilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(C)=CC=2)=C(C)C=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 IADOHFNPFBVSGF-UHFFFAOYSA-N 0.000 claims 1
- WFZQERNBKRHAIN-UHFFFAOYSA-N 2-[4-[[n-butyl-2-methyl-3-[4-(trifluoromethyl)phenyl]anilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=C(C)C=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 WFZQERNBKRHAIN-UHFFFAOYSA-N 0.000 claims 1
- XYUNARUZUYIHQQ-UHFFFAOYSA-N 2-[4-[[n-butyl-3-(4-chlorophenyl)-2-methylanilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(Cl)=CC=2)=C(C)C=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 XYUNARUZUYIHQQ-UHFFFAOYSA-N 0.000 claims 1
- PCZJCGPQUZKIRC-UHFFFAOYSA-N 2-[4-[[n-butyl-3-(4-cyanophenyl)-2-methylanilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C#N)=C(C)C=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 PCZJCGPQUZKIRC-UHFFFAOYSA-N 0.000 claims 1
- NQSRVOZQRCJMFK-UHFFFAOYSA-N 2-[4-[[n-butyl-3-(4-fluorophenyl)-2-methylanilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(F)=CC=2)=C(C)C=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 NQSRVOZQRCJMFK-UHFFFAOYSA-N 0.000 claims 1
- QPYMSJJYJSJLDH-UHFFFAOYSA-N 2-[4-[[n-butyl-3-(4-methoxyphenyl)-2-methylanilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(OC)=CC=2)=C(C)C=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 QPYMSJJYJSJLDH-UHFFFAOYSA-N 0.000 claims 1
- PKSVTAGTVUPRTI-UHFFFAOYSA-N 2-[4-[[n-butyl-3-[4-(trifluoromethyl)phenyl]anilino]methyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=CC(C=2C=CC(=CC=2)C(F)(F)F)=CC=1N(CCCC)CC1=CC=C(OCC(O)=O)C(C)=C1 PKSVTAGTVUPRTI-UHFFFAOYSA-N 0.000 claims 1
- DJPKXZIMROQBTG-UHFFFAOYSA-N 2-[4-[butyl-[2-methyl-3-[4-(trifluoromethyl)phenyl]phenyl]sulfamoyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=C(OCC(O)=O)C(C)=CC=1S(=O)(=O)N(CCCC)C(C=1C)=CC=CC=1C1=CC=C(C(F)(F)F)C=C1 DJPKXZIMROQBTG-UHFFFAOYSA-N 0.000 claims 1
- IBRDZTWPODVPSV-UHFFFAOYSA-N 2-[4-[butyl-[3-[4-(trifluoromethyl)phenyl]phenyl]sulfamoyl]-2-methylphenoxy]acetic acid Chemical compound C=1C=C(OCC(O)=O)C(C)=CC=1S(=O)(=O)N(CCCC)C(C=1)=CC=CC=1C1=CC=C(C(F)(F)F)C=C1 IBRDZTWPODVPSV-UHFFFAOYSA-N 0.000 claims 1
- KXEDACREUUFVAI-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[4-(trifluoromethyl)phenyl]methyl-[6-[4-(trifluoromethyl)phenyl]pyridin-2-yl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CN(CC=2C=CC(=CC=2)C(F)(F)F)C=2N=C(C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 KXEDACREUUFVAI-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- 125000006164 6-membered heteroaryl group Chemical group 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
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| PCT/EP2003/006416 WO2004000762A2 (en) | 2002-06-20 | 2003-06-18 | Propionic acid derivatives and their use as hppars activators |
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| JP2005534673A JP2005534673A (ja) | 2005-11-17 |
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| DE602004009295T2 (de) | 2003-01-14 | 2008-07-03 | Arena Pharmaceuticals, Inc., San Diego | 1,2,3-trisubstituierte aryl- und heteroarylderivate als modulatoren des metabolismus zur vorbeugung und behandlung von metabolismus-bedingten krankheiten wie diabetes oder hyperglykämie |
| WO2004083597A1 (en) | 2003-03-19 | 2004-09-30 | Varco I/P, Inc. | Apparatus and method for moving drilled cuttings |
| US7244763B2 (en) | 2003-04-17 | 2007-07-17 | Warner Lambert Company Llc | Compounds that modulate PPAR activity and methods of preparation |
| AR045047A1 (es) * | 2003-07-11 | 2005-10-12 | Arena Pharm Inc | Derivados arilo y heteroarilo trisustituidos como moduladores del metabolismo y de la profilaxis y tratamiento de desordenes relacionados con los mismos |
| EP2292620A3 (en) | 2003-07-14 | 2011-06-22 | Arena Pharmaceuticals, Inc. | Fused-aryl and heteroaryl derivatives as modulators of metabolism and the prohylaxis and treatment of disorders related thereto |
| WO2005007627A1 (ja) * | 2003-07-18 | 2005-01-27 | Nihon Nohyaku Co., Ltd. | フェニルピリジン誘導体、その中間体及びこれを有効成分とする除草剤 |
| US8053598B2 (en) | 2004-05-05 | 2011-11-08 | High Point Pharmaceuticals, Llc | Compounds, their preparation and use |
| ATE486055T1 (de) | 2004-05-05 | 2010-11-15 | High Point Pharmaceuticals Llc | Neue verbindungen, ihre herstellung und verwendung |
| CA2571665C (en) | 2004-06-22 | 2010-08-31 | Varco I/P, Inc. | Apparatus and method for moving drill cuttings |
| DE102004046623A1 (de) * | 2004-09-25 | 2006-03-30 | Bayer Healthcare Ag | Neue Pyrimidin-Derivate und ihre Verwendung |
| MY148521A (en) | 2005-01-10 | 2013-04-30 | Arena Pharm Inc | Substituted pyridinyl and pyrimidinyl derivatives as modulators of metabolism and the treatment of disorders related thereto |
| US7301033B2 (en) | 2005-01-27 | 2007-11-27 | Kowa Co., Ltd. | PPAR-activating compound |
| JP5052511B2 (ja) | 2005-06-30 | 2012-10-17 | ハイ ポイント ファーマシューティカルズ，エルエルシー | Ｐｐａｒデルタ活性化因子としてのフェノキシ酢酸 |
| CA2631390C (en) | 2005-12-22 | 2014-03-11 | Per Sauerberg | Phenoxy acetic acids as ppar delta activators |
| JP2009529512A (ja) | 2006-03-09 | 2009-08-20 | ハイ ポイント ファーマシューティカルズ，リミティド ライアビリティ カンパニー | 新規な化合物、それらの製造法、及び使用法 |
| RU2538276C2 (ru) * | 2009-04-23 | 2015-01-10 | Пирамал Имэджинг СА | Новые прекурсорные молекулы для меченных f-18 пэт радиоактивных индикаторов |
| WO2011002814A2 (en) * | 2009-06-30 | 2011-01-06 | Ligand Pharmaceuticals Inc. | Biaryl oxyacetic acid compounds |
| JP2012041325A (ja) | 2010-08-23 | 2012-03-01 | Bayer Cropscience Ag | オキサジアゾリノン誘導体およびその有害生物の防除用途 |
| PH12013500547A1 (en) | 2010-09-22 | 2013-06-10 | Arena Pharm Inc | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| EP3043789B1 (en) | 2013-09-09 | 2020-07-08 | vTv Therapeutics LLC | Use of a ppar-delta agonists for treating muscle atrophy |
| ES2995737T3 (en) | 2015-01-06 | 2025-02-11 | Arena Pharm Inc | Compound for use in treating conditions related to the s1p1 receptor |
| MA42807A (fr) | 2015-06-22 | 2018-07-25 | Arena Pharm Inc | Sel l-arginine cristallin d'acide (r)-2-(7-(4-cyclopentyl-3-(trifluorométhyl)benzyloxy)-1,2,3,4-tétrahydrocyclo-penta[b]indol-3-yl)acétique (composé 1) pour une utilisation dans des troubles associés au récepteur de s1p1 |
| WO2018151873A1 (en) | 2017-02-16 | 2018-08-23 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of primary biliary cholangitis |
| EP3801459B1 (en) | 2018-06-06 | 2024-08-07 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the s1p1 receptor |
| WO2023147309A1 (en) | 2022-01-25 | 2023-08-03 | Reneo Pharmaceuticals, Inc. | Use of ppar-delta agonists in the treatment of disease |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2320387A1 (de) * | 1973-04-21 | 1974-10-31 | Boehringer Mannheim Gmbh | Phenoxyalkylcarbonsaeurederivate und verfahren zur herstellung derselben |
| GB1503953A (en) * | 1974-06-04 | 1978-03-15 | Fujisawa Pharmaceutical Co | Substituted-phenyl substituted-alkyl ethers and the preparation thereof |
| US4214094A (en) * | 1977-03-30 | 1980-07-22 | Fujisawa Pharmaceutical Co., Ltd. | Substituted-phenyl substituted-alkyl ethers and the preparation thereof |
| GB9306453D0 (en) * | 1993-03-29 | 1993-05-19 | Zeneca Ltd | Heterocyclic derivatives |
| US6506757B1 (en) * | 1998-03-10 | 2003-01-14 | Ono Pharmaceutical Co., Ltd. | Carboxylic acid derivatives and drugs containing the same as the active ingredient |
| GB9822473D0 (en) * | 1998-10-16 | 1998-12-09 | Glaxo Group Ltd | Chemical compounds |
| HUP0302306A3 (en) * | 2000-10-05 | 2005-02-28 | Bayer Ag | Propionic acid derivatives with ppar-alpha activating properties |
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2002
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2003
- 2003-06-18 IL IL16547703A patent/IL165477A0/xx unknown
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- 2003-06-18 MX MXPA04012858A patent/MXPA04012858A/es active IP Right Grant
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- 2003-06-18 CA CA002489359A patent/CA2489359A1/en not_active Abandoned
- 2003-06-18 WO PCT/EP2003/006416 patent/WO2004000762A2/en not_active Ceased
- 2003-06-18 NZ NZ537209A patent/NZ537209A/en unknown
- 2003-06-18 US US10/518,778 patent/US7199239B2/en not_active Expired - Fee Related
- 2003-06-18 JP JP2004514762A patent/JP2005534673A/ja active Pending
- 2003-06-18 AU AU2003245963A patent/AU2003245963C1/en not_active Ceased
- 2003-06-18 PL PL03375075A patent/PL375075A1/xx not_active Application Discontinuation
- 2003-06-18 CN CNB038193221A patent/CN100349856C/zh not_active Expired - Fee Related
- 2003-06-18 BR BR0311935-1A patent/BR0311935A/pt not_active IP Right Cessation
- 2003-06-18 EP EP03738057A patent/EP1513795A2/en not_active Withdrawn
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2004
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- 2004-12-03 NO NO20045327A patent/NO20045327L/no not_active Application Discontinuation
- 2004-12-13 ZA ZA200410054A patent/ZA200410054B/xx unknown
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