JP2004518702A5 - - Google Patents
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- Publication number
- JP2004518702A5 JP2004518702A5 JP2002562729A JP2002562729A JP2004518702A5 JP 2004518702 A5 JP2004518702 A5 JP 2004518702A5 JP 2002562729 A JP2002562729 A JP 2002562729A JP 2002562729 A JP2002562729 A JP 2002562729A JP 2004518702 A5 JP2004518702 A5 JP 2004518702A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- thiazol
- phenoxy
- propionic acid
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 26
- -1 4- (1- [2- (2-Fluoro-4-trifluoromethyl-phenyl) -4-methyl-thiazol-5-yl] -ethoxy) -2-methylphenoxy Chemical group 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 101000741788 Homo sapiens Peroxisome proliferator-activated receptor alpha Proteins 0.000 claims 4
- 102100038831 Peroxisome proliferator-activated receptor alpha Human genes 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 208000022531 anorexia Diseases 0.000 claims 3
- 206010061428 decreased appetite Diseases 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 3
- ZUGQWAYOWCBWGM-UHFFFAOYSA-N 2-[4-[[2-[2-fluoro-4-(trifluoromethyl)phenyl]-4-methyl-1,3-thiazol-5-yl]methylsulfanyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound CC=1N=C(C=2C(=CC(=CC=2)C(F)(F)F)F)SC=1CSC1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 ZUGQWAYOWCBWGM-UHFFFAOYSA-N 0.000 claims 2
- RRDUKUBKIRKLQP-OAHLLOKOSA-N 2-methyl-2-[2-methyl-4-[(1r)-1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethoxy]phenoxy]propanoic acid Chemical compound O([C@H](C)C1=C(N=C(S1)C=1C=CC(=CC=1)C(F)(F)F)C)C1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 RRDUKUBKIRKLQP-OAHLLOKOSA-N 0.000 claims 2
- RRDUKUBKIRKLQP-HNNXBMFYSA-N 2-methyl-2-[2-methyl-4-[(1s)-1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethoxy]phenoxy]propanoic acid Chemical compound O([C@@H](C)C1=C(N=C(S1)C=1C=CC(=CC=1)C(F)(F)F)C)C1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 RRDUKUBKIRKLQP-HNNXBMFYSA-N 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 2
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 2
- 206010022489 Insulin Resistance Diseases 0.000 claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 125000004494 ethyl ester group Chemical group 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- AOUIGDBKRLOZRQ-UHFFFAOYSA-N 2-[2-methyl-4-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethoxy]phenoxy]acetic acid Chemical compound S1C(C=2C=CC(=CC=2)C(F)(F)F)=NC(C)=C1C(C)OC1=CC=C(OCC(O)=O)C(C)=C1 AOUIGDBKRLOZRQ-UHFFFAOYSA-N 0.000 claims 1
- ACNJQJVNIHENMJ-UHFFFAOYSA-N 2-[4-[1-[2-(3,4-dichlorophenyl)-4-methyl-1,3-thiazol-5-yl]ethoxy]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound S1C(C=2C=C(Cl)C(Cl)=CC=2)=NC(C)=C1C(C)OC1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 ACNJQJVNIHENMJ-UHFFFAOYSA-N 0.000 claims 1
- JDJCZGMWUDTZHP-UHFFFAOYSA-N 2-[4-[1-[2-(4-chlorophenyl)-4-methyl-1,3-thiazol-5-yl]ethoxy]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound S1C(C=2C=CC(Cl)=CC=2)=NC(C)=C1C(C)OC1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 JDJCZGMWUDTZHP-UHFFFAOYSA-N 0.000 claims 1
- GALPDOKVVGMRBH-UHFFFAOYSA-N 2-[4-[1-[2-(4-ethylphenyl)-4-methyl-1,3-thiazol-5-yl]ethoxy]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound C1=CC(CC)=CC=C1C1=NC(C)=C(C(C)OC=2C=C(C)C(OC(C)(C)C(O)=O)=CC=2)S1 GALPDOKVVGMRBH-UHFFFAOYSA-N 0.000 claims 1
- LQAGUDSBCGFOHU-UHFFFAOYSA-N 2-[4-[1-[2-[2-fluoro-4-(trifluoromethyl)phenyl]-4-methyl-1,3-thiazol-5-yl]ethoxy]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound S1C(C=2C(=CC(=CC=2)C(F)(F)F)F)=NC(C)=C1C(C)OC1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 LQAGUDSBCGFOHU-UHFFFAOYSA-N 0.000 claims 1
- SDXLGWSTXLUGHO-UHFFFAOYSA-N 2-[4-[1-[2-[3-fluoro-4-(trifluoromethyl)phenyl]-4-methyl-1,3-thiazol-5-yl]ethoxy]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound S1C(C=2C=C(F)C(=CC=2)C(F)(F)F)=NC(C)=C1C(C)OC1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 SDXLGWSTXLUGHO-UHFFFAOYSA-N 0.000 claims 1
- ISQOFVFXEZIWTH-UHFFFAOYSA-N 2-[4-[cyclopentyl-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methoxy]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1C(C1CCCC1)OC1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 ISQOFVFXEZIWTH-UHFFFAOYSA-N 0.000 claims 1
- GPDKHYMYBCWQSD-LJQANCHMSA-N 2-methyl-2-[2-methyl-4-[(1r)-1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]propoxy]phenoxy]propanoic acid Chemical compound O([C@H](CC)C1=C(N=C(S1)C=1C=CC(=CC=1)C(F)(F)F)C)C1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 GPDKHYMYBCWQSD-LJQANCHMSA-N 0.000 claims 1
- GPDKHYMYBCWQSD-IBGZPJMESA-N 2-methyl-2-[2-methyl-4-[(1s)-1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]propoxy]phenoxy]propanoic acid Chemical compound O([C@@H](CC)C1=C(N=C(S1)C=1C=CC(=CC=1)C(F)(F)F)C)C1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 GPDKHYMYBCWQSD-IBGZPJMESA-N 0.000 claims 1
- IZCWEGLTGIXGEK-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[1-[2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethoxy]phenoxy]propanoic acid Chemical compound C=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1C(C)OC1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 IZCWEGLTGIXGEK-UHFFFAOYSA-N 0.000 claims 1
- TUXGYOGLJLNSLC-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]-2-phenylethoxy]phenoxy]propanoic acid Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1C(OC=1C=C(C)C(OC(C)(C)C(O)=O)=CC=1)CC1=CC=CC=C1 TUXGYOGLJLNSLC-UHFFFAOYSA-N 0.000 claims 1
- ACLIMENRFRVCSU-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]but-3-enoxy]phenoxy]propanoic acid Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1C(CC=C)OC1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 ACLIMENRFRVCSU-UHFFFAOYSA-N 0.000 claims 1
- DOYOGUXJFXYZPD-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]butoxy]phenoxy]propanoic acid Chemical compound S1C(C=2C=CC(=CC=2)C(F)(F)F)=NC(C)=C1C(CCC)OC1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 DOYOGUXJFXYZPD-UHFFFAOYSA-N 0.000 claims 1
- RRDUKUBKIRKLQP-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethoxy]phenoxy]propanoic acid Chemical compound S1C(C=2C=CC(=CC=2)C(F)(F)F)=NC(C)=C1C(C)OC1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 RRDUKUBKIRKLQP-UHFFFAOYSA-N 0.000 claims 1
- MEAQHQOZORFODX-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethylsulfanyl]phenoxy]propanoic acid Chemical compound S1C(C=2C=CC(=CC=2)C(F)(F)F)=NC(C)=C1C(C)SC1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 MEAQHQOZORFODX-UHFFFAOYSA-N 0.000 claims 1
- ZOLXTFMSCKSTOO-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]pentoxy]phenoxy]propanoic acid Chemical compound S1C(C=2C=CC(=CC=2)C(F)(F)F)=NC(C)=C1C(CCCC)OC1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 ZOLXTFMSCKSTOO-UHFFFAOYSA-N 0.000 claims 1
- GPDKHYMYBCWQSD-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]propoxy]phenoxy]propanoic acid Chemical compound S1C(C=2C=CC(=CC=2)C(F)(F)F)=NC(C)=C1C(CC)OC1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 GPDKHYMYBCWQSD-UHFFFAOYSA-N 0.000 claims 1
- SINFYHIOGKADPP-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]propylsulfanyl]phenoxy]propanoic acid Chemical compound S1C(C=2C=CC(=CC=2)C(F)(F)F)=NC(C)=C1C(CC)SC1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 SINFYHIOGKADPP-UHFFFAOYSA-N 0.000 claims 1
- UNSKNEREBDWKII-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[2-[2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]propan-2-yloxy]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(OC(C)(C)C=2SC(=NC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 UNSKNEREBDWKII-UHFFFAOYSA-N 0.000 claims 1
- HQHRFQAEWBBOAE-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[2-[2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]propan-2-ylsulfanyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(SC(C)(C)C=2SC(=NC=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 HQHRFQAEWBBOAE-UHFFFAOYSA-N 0.000 claims 1
- YIJZPRXQAKJHNE-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[2-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]propan-2-yloxy]phenoxy]propanoic acid Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1C(C)(C)OC1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 YIJZPRXQAKJHNE-UHFFFAOYSA-N 0.000 claims 1
- MNYRVRCNVSMQRM-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[2-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]propan-2-ylsulfanyl]phenoxy]propanoic acid Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1C(C)(C)SC1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 MNYRVRCNVSMQRM-UHFFFAOYSA-N 0.000 claims 1
- IVPLIRNRYVHYOT-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]cyclohexa-2,4-dien-1-yl]methoxy]phenoxy]propanoic acid Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1C1(COC=2C=C(C)C(OC(C)(C)C(O)=O)=CC=2)CC=CC=C1 IVPLIRNRYVHYOT-UHFFFAOYSA-N 0.000 claims 1
- LQLKLIQPTDBTIF-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methoxy]phenoxy]propanoic acid Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1COC1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 LQLKLIQPTDBTIF-UHFFFAOYSA-N 0.000 claims 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 1
- 206010006550 Bulimia nervosa Diseases 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 206010020710 Hyperphagia Diseases 0.000 claims 1
- 206010029216 Nervousness Diseases 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 239000000556 agonist Substances 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- ZXHJTFHHPIOPGB-UHFFFAOYSA-N ethyl 2-[2-methyl-4-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethoxy]phenoxy]acetate Chemical compound C1=C(C)C(OCC(=O)OCC)=CC=C1OC(C)C1=C(C)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 ZXHJTFHHPIOPGB-UHFFFAOYSA-N 0.000 claims 1
- DBURNDRLWVLANW-UHFFFAOYSA-N ethyl 2-[4-[1-[2-(3,4-dichlorophenyl)-4-methyl-1,3-thiazol-5-yl]ethoxy]-2-methylphenoxy]-2-methylpropanoate Chemical compound C1=C(C)C(OC(C)(C)C(=O)OCC)=CC=C1OC(C)C1=C(C)N=C(C=2C=C(Cl)C(Cl)=CC=2)S1 DBURNDRLWVLANW-UHFFFAOYSA-N 0.000 claims 1
- HFOMNFSKPLSQCE-UHFFFAOYSA-N ethyl 2-[4-[1-[2-(4-chlorophenyl)-4-methyl-1,3-thiazol-5-yl]ethoxy]-2-methylphenoxy]-2-methylpropanoate Chemical compound C1=C(C)C(OC(C)(C)C(=O)OCC)=CC=C1OC(C)C1=C(C)N=C(C=2C=CC(Cl)=CC=2)S1 HFOMNFSKPLSQCE-UHFFFAOYSA-N 0.000 claims 1
- LWZJOPATGVBMKD-UHFFFAOYSA-N ethyl 2-[4-[1-[2-(4-ethylphenyl)-4-methyl-1,3-thiazol-5-yl]ethoxy]-2-methylphenoxy]-2-methylpropanoate Chemical compound C1=C(C)C(OC(C)(C)C(=O)OCC)=CC=C1OC(C)C1=C(C)N=C(C=2C=CC(CC)=CC=2)S1 LWZJOPATGVBMKD-UHFFFAOYSA-N 0.000 claims 1
- MOCCWJXYISRYQO-UHFFFAOYSA-N ethyl 2-[4-[1-[2-[3-fluoro-4-(trifluoromethyl)phenyl]-4-methyl-1,3-thiazol-5-yl]ethoxy]-2-methylphenoxy]-2-methylpropanoate Chemical compound C1=C(C)C(OC(C)(C)C(=O)OCC)=CC=C1OC(C)C1=C(C)N=C(C=2C=C(F)C(=CC=2)C(F)(F)F)S1 MOCCWJXYISRYQO-UHFFFAOYSA-N 0.000 claims 1
- WZLKBWUOLKNURJ-UHFFFAOYSA-N ethyl 2-[4-[cyclopentyl-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methoxy]-2-methylphenoxy]-2-methylpropanoate Chemical compound C1=C(C)C(OC(C)(C)C(=O)OCC)=CC=C1OC(C1=C(N=C(S1)C=1C=CC(=CC=1)C(F)(F)F)C)C1CCCC1 WZLKBWUOLKNURJ-UHFFFAOYSA-N 0.000 claims 1
- VVSDRJWDUWKJEQ-QGZVFWFLSA-N ethyl 2-methyl-2-[2-methyl-4-[(1r)-1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethoxy]phenoxy]propanoate Chemical compound C1=C(C)C(OC(C)(C)C(=O)OCC)=CC=C1O[C@H](C)C1=C(C)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 VVSDRJWDUWKJEQ-QGZVFWFLSA-N 0.000 claims 1
- DUHMSMHVKCZPHW-OAQYLSRUSA-N ethyl 2-methyl-2-[2-methyl-4-[(1r)-1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]propoxy]phenoxy]propanoate Chemical compound C1=C(C)C(OC(C)(C)C(=O)OCC)=CC=C1O[C@H](CC)C1=C(C)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 DUHMSMHVKCZPHW-OAQYLSRUSA-N 0.000 claims 1
- VVSDRJWDUWKJEQ-KRWDZBQOSA-N ethyl 2-methyl-2-[2-methyl-4-[(1s)-1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethoxy]phenoxy]propanoate Chemical compound C1=C(C)C(OC(C)(C)C(=O)OCC)=CC=C1O[C@@H](C)C1=C(C)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 VVSDRJWDUWKJEQ-KRWDZBQOSA-N 0.000 claims 1
- DUHMSMHVKCZPHW-NRFANRHFSA-N ethyl 2-methyl-2-[2-methyl-4-[(1s)-1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]propoxy]phenoxy]propanoate Chemical compound C1=C(C)C(OC(C)(C)C(=O)OCC)=CC=C1O[C@@H](CC)C1=C(C)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 DUHMSMHVKCZPHW-NRFANRHFSA-N 0.000 claims 1
- NEMPFGQAFNBACF-UHFFFAOYSA-N ethyl 2-methyl-2-[2-methyl-4-[1-[2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethoxy]phenoxy]propanoate Chemical compound C1=C(C)C(OC(C)(C)C(=O)OCC)=CC=C1OC(C)C1=CN=C(C=2C=CC(=CC=2)C(F)(F)F)S1 NEMPFGQAFNBACF-UHFFFAOYSA-N 0.000 claims 1
- QTURWFQIKQVYCZ-UHFFFAOYSA-N ethyl 2-methyl-2-[2-methyl-4-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]-2-phenylethoxy]phenoxy]propanoate Chemical compound C1=C(C)C(OC(C)(C)C(=O)OCC)=CC=C1OC(C1=C(N=C(S1)C=1C=CC(=CC=1)C(F)(F)F)C)CC1=CC=CC=C1 QTURWFQIKQVYCZ-UHFFFAOYSA-N 0.000 claims 1
- OZAASIUSAUEJBC-UHFFFAOYSA-N ethyl 2-methyl-2-[2-methyl-4-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]but-3-enoxy]phenoxy]propanoate Chemical compound C1=C(C)C(OC(C)(C)C(=O)OCC)=CC=C1OC(CC=C)C1=C(C)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 OZAASIUSAUEJBC-UHFFFAOYSA-N 0.000 claims 1
- WBMZDAQGXFDTBQ-UHFFFAOYSA-N ethyl 2-methyl-2-[2-methyl-4-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]butoxy]phenoxy]propanoate Chemical compound S1C(C=2C=CC(=CC=2)C(F)(F)F)=NC(C)=C1C(CCC)OC1=CC=C(OC(C)(C)C(=O)OCC)C(C)=C1 WBMZDAQGXFDTBQ-UHFFFAOYSA-N 0.000 claims 1
- VVSDRJWDUWKJEQ-UHFFFAOYSA-N ethyl 2-methyl-2-[2-methyl-4-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethoxy]phenoxy]propanoate Chemical compound C1=C(C)C(OC(C)(C)C(=O)OCC)=CC=C1OC(C)C1=C(C)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 VVSDRJWDUWKJEQ-UHFFFAOYSA-N 0.000 claims 1
- UXFXXVKVEXOMHE-UHFFFAOYSA-N ethyl 2-methyl-2-[2-methyl-4-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethylsulfanyl]phenoxy]propanoate Chemical compound C1=C(C)C(OC(C)(C)C(=O)OCC)=CC=C1SC(C)C1=C(C)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 UXFXXVKVEXOMHE-UHFFFAOYSA-N 0.000 claims 1
- JOZKDSFBDDGHOS-UHFFFAOYSA-N ethyl 2-methyl-2-[2-methyl-4-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]pentoxy]phenoxy]propanoate Chemical compound S1C(C=2C=CC(=CC=2)C(F)(F)F)=NC(C)=C1C(CCCC)OC1=CC=C(OC(C)(C)C(=O)OCC)C(C)=C1 JOZKDSFBDDGHOS-UHFFFAOYSA-N 0.000 claims 1
- DUHMSMHVKCZPHW-UHFFFAOYSA-N ethyl 2-methyl-2-[2-methyl-4-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]propoxy]phenoxy]propanoate Chemical compound C1=C(C)C(OC(C)(C)C(=O)OCC)=CC=C1OC(CC)C1=C(C)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 DUHMSMHVKCZPHW-UHFFFAOYSA-N 0.000 claims 1
- JBQDPMDKMBYJDD-UHFFFAOYSA-N ethyl 2-methyl-2-[2-methyl-4-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]propylsulfanyl]phenoxy]propanoate Chemical compound C1=C(C)C(OC(C)(C)C(=O)OCC)=CC=C1SC(CC)C1=C(C)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 JBQDPMDKMBYJDD-UHFFFAOYSA-N 0.000 claims 1
- WZJRDOUGNQVPHT-UHFFFAOYSA-N ethyl 2-methyl-2-[2-methyl-4-[2-[2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]propan-2-yloxy]phenoxy]propanoate Chemical compound C1=C(C)C(OC(C)(C)C(=O)OCC)=CC=C1OC(C)(C)C1=CN=C(C=2C=CC(=CC=2)C(F)(F)F)S1 WZJRDOUGNQVPHT-UHFFFAOYSA-N 0.000 claims 1
- WYKFKUGBMNNIEZ-UHFFFAOYSA-N ethyl 2-methyl-2-[2-methyl-4-[2-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]propan-2-ylsulfanyl]phenoxy]propanoate Chemical compound C1=C(C)C(OC(C)(C)C(=O)OCC)=CC=C1SC(C)(C)C1=C(C)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 WYKFKUGBMNNIEZ-UHFFFAOYSA-N 0.000 claims 1
- WBCQUDYYSJMYGF-UHFFFAOYSA-N ethyl 2-methyl-2-[2-methyl-4-[[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]cyclohexa-2,4-dien-1-yl]methoxy]phenoxy]propanoate Chemical compound C1=C(C)C(OC(C)(C)C(=O)OCC)=CC=C1OCC1(C2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)C)C=CC=CC1 WBCQUDYYSJMYGF-UHFFFAOYSA-N 0.000 claims 1
- NCNIULXXTBGJFD-UHFFFAOYSA-N ethyl 2-methyl-2-[2-methyl-4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methoxy]phenoxy]propanoate Chemical compound C1=C(C)C(OC(C)(C)C(=O)OCC)=CC=C1OCC1=C(C)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 NCNIULXXTBGJFD-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 235000020830 overeating Nutrition 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
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| US7041691B1 (en) | 1999-06-30 | 2006-05-09 | Amgen Inc. | Compounds for the modulation of PPARγ activity |
| CA2410382A1 (en) | 2000-05-26 | 2002-11-25 | Nippon Shinyaku Co., Ltd. | Heterocyclic compounds |
| US20030171399A1 (en) | 2000-06-28 | 2003-09-11 | Tularik Inc. | Quinolinyl and benzothiazolyl modulators |
| GB0031109D0 (en) | 2000-12-20 | 2001-01-31 | Glaxo Group Ltd | Chemical compounds |
| US20040072838A1 (en) | 2000-12-20 | 2004-04-15 | Pierette Banker | Thiazole and oxazole derivatives as activators of human peroxisome proliferator activated receptors |
| US7138403B2 (en) * | 2001-08-13 | 2006-11-21 | Janssen Pharmaceutica N.V. | 2,4,5-trisubstituted thiazolyl derivatives and their antiinflammatory activity |
| AU2003214932A1 (en) | 2002-02-25 | 2003-09-09 | Eli Lilly And Company | Peroxisome proliferator activated receptor modulators |
| DE60315603T2 (de) | 2002-02-25 | 2008-05-21 | Eli Lilly And Co., Indianapolis | Modulatoren von peroxisome proliferator-aktivierten rezeptoren |
| US20030207924A1 (en) * | 2002-03-07 | 2003-11-06 | Xue-Min Cheng | Compounds that modulate PPAR activity and methods of preparation |
| US6833380B2 (en) | 2002-03-07 | 2004-12-21 | Warner-Lambert Company, Llc | Compounds that modulate PPAR activity and methods of preparation |
| US6875780B2 (en) | 2002-04-05 | 2005-04-05 | Warner-Lambert Company | Compounds that modulate PPAR activity and methods for their preparation |
| US7244763B2 (en) | 2003-04-17 | 2007-07-17 | Warner Lambert Company Llc | Compounds that modulate PPAR activity and methods of preparation |
| US6987118B2 (en) | 2003-05-21 | 2006-01-17 | Pfizer Inc. | Tetrahydroisoquinoline derivatives as PPAR-alpha activators |
| MXPA05013146A (es) | 2003-06-06 | 2006-03-17 | Hoffmann La Roche | Derivados de anilina. |
| AU2004255580B2 (en) | 2003-07-02 | 2009-10-08 | F. Hoffmann-La Roche Ag | Indolyl derivatives substituted with a thiazole ring and their use as PPAR modulators |
| ATE542793T1 (de) | 2003-09-19 | 2012-02-15 | Janssen Pharmaceutica Nv | 4-((phenoxyalkyl)thio)-phenoxyessigsäuren und analoga |
| US7223761B2 (en) | 2003-10-03 | 2007-05-29 | Amgen Inc. | Salts and polymorphs of a potent antidiabetic compound |
| KR20070004769A (ko) * | 2004-02-27 | 2007-01-09 | 암젠 인코포레이션 | 대사 장애의 치료에 사용되는 화합물, 약제학적 조성물 및그 사용방법 |
| US7968723B2 (en) | 2004-05-05 | 2011-06-28 | High Point Pharmaceuticals, Llc | Compounds, their preparation and use |
| EP1745014B1 (en) | 2004-05-05 | 2011-07-06 | High Point Pharmaceuticals, LLC | Novel compounds, their preparation and use |
| MY147518A (en) * | 2004-09-15 | 2012-12-31 | Janssen Pharmaceutica Nv | 4-((phenoxyalkyl)thio)-phenoxyacetic acids and analogs |
| MY145712A (en) | 2004-09-15 | 2012-03-30 | Janssen Pharmaceutica Nv | 4-((phenoxyalkyl)thio)-phenoxyacetic acids and analogs |
| CA2598821C (en) * | 2004-12-31 | 2011-05-31 | Heonjoong Kang | Organoselenium containing compounds and their use |
| BRPI0606232A2 (pt) * | 2005-02-25 | 2009-06-09 | Kang Heonjoong | derivados de tiazole como os ligantes delta ppar e seus processos de produção |
| WO2006091047A1 (en) | 2005-02-25 | 2006-08-31 | Heonjoong Kang | Thiazole derivatives as ppar delta ligands and their manufacturing process |
| US7465804B2 (en) | 2005-05-20 | 2008-12-16 | Amgen Inc. | Compounds, pharmaceutical compositions and methods for their use in treating metabolic disorders |
| CA2613365C (en) | 2005-06-30 | 2013-08-13 | Novo-Nordisk A/S | Phenoxy acetic acids as ppar delta activators |
| JO3006B1 (ar) | 2005-09-14 | 2016-09-05 | Janssen Pharmaceutica Nv | املاح ليسين مبتكرة من مشتقات حامض 4-((فينوكسي الكيل)ثيو) فينوكسي الخليك |
| AU2006291234A1 (en) | 2005-09-14 | 2007-03-22 | Amgen Inc. | Conformationally constrained 3- (4-hydroxy-phenyl) - substituted-propanoic acids useful for treating metabolic disorders |
| NZ568488A (en) | 2005-12-22 | 2011-07-29 | High Point Pharmaceuticals Llc | Phenoxy acetic acids as PPAR delta activators |
| CN101007790B (zh) * | 2006-01-27 | 2011-03-30 | 北京摩力克科技有限公司 | 草氨酸衍生物、其制备方法和医药用途 |
| US7943612B2 (en) | 2006-03-09 | 2011-05-17 | High Point Pharmaceuticals, Llc | Compounds that modulate PPAR activity, their preparation and use |
| UY30288A1 (es) | 2006-04-18 | 2007-08-31 | Janssen Pharmaceutica Nv | Derivados del ácido benzoazepin-oxi-acético como agonistas de ppar-delta usados para aumentar hdl-c. reducir ldl-c y reducir colesterol |
| US7687526B2 (en) | 2006-09-07 | 2010-03-30 | Amgen Inc. | Benzo-fused compounds for use in treating metabolic disorders |
| WO2008030520A1 (en) | 2006-09-07 | 2008-03-13 | Amgen Inc. | Heterocyclic gpr40 modulators |
| KR100951653B1 (ko) | 2006-12-02 | 2010-04-07 | 재단법인서울대학교산학협력재단 | 퍼록시솜 증식자 활성화 수용체 리간드 아릴 화합물 및이들 화합물의 용도 |
| KR100954237B1 (ko) | 2007-01-08 | 2010-04-21 | 재단법인서울대학교산학협력재단 | 퍼록시솜 증식자 활성화 수용체 델타 리간드 티아졸 화합물및 이를 함유하는 의약, 화장품 및 건강식품 조성물 |
| PE20090159A1 (es) | 2007-03-08 | 2009-02-21 | Plexxikon Inc | COMPUESTOS DERIVADOS DE ACIDO INDOL-PROPIONICO COMO MODULADORES PPARs |
| WO2008130514A1 (en) | 2007-04-16 | 2008-10-30 | Amgen Inc. | Substituted biphenyl phenoxy-, thiophenyl- and aminophenylpropanoic acid gpr40 modulators |
| BRPI0818253A2 (pt) | 2007-10-10 | 2015-04-07 | Amgen Inc | Moduladores de gpr40 bifenil substituídos |
| EP2260017A1 (en) | 2008-03-06 | 2010-12-15 | Amgen, Inc | Conformationally constrained carboxylic acid derivatives useful for treating metabolic disorders |
| ES2450567T3 (es) | 2008-10-15 | 2014-03-25 | Amgen, Inc | Moduladores de GPR40 espirocíclicos |
| US20120316346A1 (en) * | 2010-02-25 | 2012-12-13 | Snu R & Db Foundation | Selenalzole derivative having ligand which activates peroxisome proliferator activated receptor (ppar), preparing method thereof and usage of the chemical compounds |
| US20120094959A1 (en) | 2010-10-19 | 2012-04-19 | Bonnie Blazer-Yost | Treatment of cystic diseases |
| EP3043789B1 (en) | 2013-09-09 | 2020-07-08 | vTv Therapeutics LLC | Use of a ppar-delta agonists for treating muscle atrophy |
| WO2023147309A1 (en) | 2022-01-25 | 2023-08-03 | Reneo Pharmaceuticals, Inc. | Use of ppar-delta agonists in the treatment of disease |
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| US4434164A (en) * | 1981-06-01 | 1984-02-28 | Pfizer Inc. | Crystalline benzothiazine dioxide salts |
| US4623486A (en) * | 1985-05-29 | 1986-11-18 | Pfizer Inc. | [4-substituted benzoyloxy]-N-substituted-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxides having anti-arthritic activity |
| GB9914977D0 (en) * | 1999-06-25 | 1999-08-25 | Glaxo Group Ltd | Chemical compounds |
| PE20011010A1 (es) * | 1999-12-02 | 2001-10-18 | Glaxo Group Ltd | Oxazoles y tiazoles sustituidos como agonista del receptor activado por el proliferador de peroxisomas humano |
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- 2001-12-19 EP EP01994305A patent/EP1343773B1/en not_active Expired - Lifetime
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