DE60315603T2 - Modulatoren von peroxisome proliferator-aktivierten rezeptoren - Google Patents
Modulatoren von peroxisome proliferator-aktivierten rezeptoren Download PDFInfo
- Publication number
- DE60315603T2 DE60315603T2 DE60315603T DE60315603T DE60315603T2 DE 60315603 T2 DE60315603 T2 DE 60315603T2 DE 60315603 T DE60315603 T DE 60315603T DE 60315603 T DE60315603 T DE 60315603T DE 60315603 T2 DE60315603 T2 DE 60315603T2
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- DE
- Germany
- Prior art keywords
- methyl
- phenyl
- thiazol
- trifluoromethylphenyl
- propionic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 title description 33
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 title description 33
- 150000001875 compounds Chemical class 0.000 claims abstract description 233
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 47
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 125000003118 aryl group Chemical group 0.000 claims abstract description 17
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 10
- 125000005110 aryl thio group Chemical group 0.000 claims abstract description 9
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 58
- -1 2-chloro-6-fluorophenyl Chemical group 0.000 claims description 48
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
- 238000011282 treatment Methods 0.000 claims description 38
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
- 241000124008 Mammalia Species 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 11
- 208000011580 syndromic disease Diseases 0.000 claims description 11
- 206010012601 diabetes mellitus Diseases 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 201000001320 Atherosclerosis Diseases 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 7
- 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 5
- YNHDIWFFCZAIOJ-UHFFFAOYSA-N 3-[2-methyl-4-[2-[5-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]propoxy]phenyl]propanoic acid Chemical compound N1=C(C=2C=CC(=CC=2)C(F)(F)F)OC(C)=C1C(C)COC1=CC=C(CCC(O)=O)C(C)=C1 YNHDIWFFCZAIOJ-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- FQDZPJAAONFQSD-LJQANCHMSA-N 2-[2-methyl-4-[(1r)-1-[4-(2-phenylethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethoxy]phenoxy]acetic acid Chemical compound O([C@H](C)C1=C(N=C(S1)C=1C=CC(=CC=1)C(F)(F)F)CCC=1C=CC=CC=1)C1=CC=C(OCC(O)=O)C(C)=C1 FQDZPJAAONFQSD-LJQANCHMSA-N 0.000 claims description 4
- WYWYSSDSZATLTG-UHFFFAOYSA-N 2-[4-[1-[4-[(2-chloro-6-fluorophenoxy)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound S1C(C=2C=CC(=CC=2)C(F)(F)F)=NC(COC=2C(=CC=CC=2F)Cl)=C1C(C)SC1=CC=C(OCC(O)=O)C(C)=C1 WYWYSSDSZATLTG-UHFFFAOYSA-N 0.000 claims description 4
- RMDYKBXFBHFGJV-UHFFFAOYSA-N 2-[4-[1-[4-[2-(2-chloro-6-fluorophenyl)ethyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound S1C(C=2C=CC(=CC=2)C(F)(F)F)=NC(CCC=2C(=CC=CC=2F)Cl)=C1C(C)SC1=CC=C(OCC(O)=O)C(C)=C1 RMDYKBXFBHFGJV-UHFFFAOYSA-N 0.000 claims description 4
- XGYOUMVNQVZLBY-UHFFFAOYSA-N 2-[4-[1-[4-ethyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-5-yl]ethylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound CCC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)OC=1C(C)SC1=CC=C(OCC(O)=O)C(C)=C1 XGYOUMVNQVZLBY-UHFFFAOYSA-N 0.000 claims description 4
- BRTFMXXYTUZGKY-OAHLLOKOSA-N 3-[2-methyl-4-[(1r)-1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-5-yl]ethoxy]phenyl]propanoic acid Chemical compound O([C@H](C)C1=C(N=C(O1)C=1C=CC(=CC=1)C(F)(F)F)C)C1=CC=C(CCC(O)=O)C(C)=C1 BRTFMXXYTUZGKY-OAHLLOKOSA-N 0.000 claims description 4
- JEUYRMGHAGJHBW-UHFFFAOYSA-N 3-[2-methyl-4-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-5-yl]but-3-enoxy]phenyl]propanoic acid Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)OC=1C(CC=C)OC1=CC=C(CCC(O)=O)C(C)=C1 JEUYRMGHAGJHBW-UHFFFAOYSA-N 0.000 claims description 4
- MWRUOVTUHNCAPT-UHFFFAOYSA-N 3-[2-methyl-4-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-5-yl]butoxy]phenyl]propanoic acid Chemical compound O1C(C=2C=CC(=CC=2)C(F)(F)F)=NC(C)=C1C(CCC)OC1=CC=C(CCC(O)=O)C(C)=C1 MWRUOVTUHNCAPT-UHFFFAOYSA-N 0.000 claims description 4
- BRTFMXXYTUZGKY-UHFFFAOYSA-N 3-[2-methyl-4-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-5-yl]ethoxy]phenyl]propanoic acid Chemical compound O1C(C=2C=CC(=CC=2)C(F)(F)F)=NC(C)=C1C(C)OC1=CC=C(CCC(O)=O)C(C)=C1 BRTFMXXYTUZGKY-UHFFFAOYSA-N 0.000 claims description 4
- JURDPNPQVAXTQS-UHFFFAOYSA-N 3-[4-[1-[2-(3-cyclopentyloxyphenyl)-4-propan-2-yl-1,3-oxazol-5-yl]ethoxy]-2-methylphenyl]propanoic acid Chemical compound CC(C)C=1N=C(C=2C=C(OC3CCCC3)C=CC=2)OC=1C(C)OC1=CC=C(CCC(O)=O)C(C)=C1 JURDPNPQVAXTQS-UHFFFAOYSA-N 0.000 claims description 4
- WNPISDSTXJLULM-UHFFFAOYSA-N 3-[4-[1-[4-ethyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-5-yl]ethoxy]-2-methylphenyl]propanoic acid Chemical compound CCC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)OC=1C(C)OC1=CC=C(CCC(O)=O)C(C)=C1 WNPISDSTXJLULM-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 125000006726 (C1-C5) alkenyl group Chemical group 0.000 claims description 3
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- LLWUFBCWJUVEQD-GOSISDBHSA-N 2-[2-methyl-4-[(1r)-1-[4-(phenylsulfanylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethyl]sulfanylphenoxy]acetic acid Chemical compound S([C@H](C)C1=C(N=C(S1)C=1C=CC(=CC=1)C(F)(F)F)CSC=1C=CC=CC=1)C1=CC=C(OCC(O)=O)C(C)=C1 LLWUFBCWJUVEQD-GOSISDBHSA-N 0.000 claims description 3
- OWDQZVUICOQNRV-OAHLLOKOSA-N 2-[2-methyl-4-[(1r)-1-[4-propan-2-yl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethyl]sulfanylphenoxy]acetic acid Chemical compound S([C@H](C)C=1SC(=NC=1C(C)C)C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(OCC(O)=O)C(C)=C1 OWDQZVUICOQNRV-OAHLLOKOSA-N 0.000 claims description 3
- LLWUFBCWJUVEQD-SFHVURJKSA-N 2-[2-methyl-4-[(1s)-1-[4-(phenylsulfanylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethyl]sulfanylphenoxy]acetic acid Chemical compound S([C@@H](C)C1=C(N=C(S1)C=1C=CC(=CC=1)C(F)(F)F)CSC=1C=CC=CC=1)C1=CC=C(OCC(O)=O)C(C)=C1 LLWUFBCWJUVEQD-SFHVURJKSA-N 0.000 claims description 3
- OWDQZVUICOQNRV-HNNXBMFYSA-N 2-[2-methyl-4-[(1s)-1-[4-propan-2-yl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethyl]sulfanylphenoxy]acetic acid Chemical compound S([C@@H](C)C=1SC(=NC=1C(C)C)C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(OCC(O)=O)C(C)=C1 OWDQZVUICOQNRV-HNNXBMFYSA-N 0.000 claims description 3
- FQDZPJAAONFQSD-UHFFFAOYSA-N 2-[2-methyl-4-[1-[4-(2-phenylethyl)-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(CCC=2C=CC=CC=2)=C1C(C)OC1=CC=C(OCC(O)=O)C(C)=C1 FQDZPJAAONFQSD-UHFFFAOYSA-N 0.000 claims description 3
- XIDQRQSMCPWFBE-UHFFFAOYSA-N 2-[2-methyl-4-[1-[4-(2-phenylethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethylsulfanyl]phenoxy]acetic acid Chemical compound S1C(C=2C=CC(=CC=2)C(F)(F)F)=NC(CCC=2C=CC=CC=2)=C1C(C)SC1=CC=C(OCC(O)=O)C(C)=C1 XIDQRQSMCPWFBE-UHFFFAOYSA-N 0.000 claims description 3
- LLWUFBCWJUVEQD-UHFFFAOYSA-N 2-[2-methyl-4-[1-[4-(phenylsulfanylmethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethylsulfanyl]phenoxy]acetic acid Chemical compound S1C(C=2C=CC(=CC=2)C(F)(F)F)=NC(CSC=2C=CC=CC=2)=C1C(C)SC1=CC=C(OCC(O)=O)C(C)=C1 LLWUFBCWJUVEQD-UHFFFAOYSA-N 0.000 claims description 3
- UHZSDVNOWGZQIJ-UHFFFAOYSA-N 2-[2-methyl-4-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]-2-phenylethyl]sulfanylphenoxy]acetic acid Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1C(SC=1C=C(C)C(OCC(O)=O)=CC=1)CC1=CC=CC=C1 UHZSDVNOWGZQIJ-UHFFFAOYSA-N 0.000 claims description 3
- CJEZMYDRYWKBOK-UHFFFAOYSA-N 2-[2-methyl-4-[1-[4-phenyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethylsulfanyl]phenoxy]acetic acid Chemical compound S1C(C=2C=CC(=CC=2)C(F)(F)F)=NC(C=2C=CC=CC=2)=C1C(C)SC1=CC=C(OCC(O)=O)C(C)=C1 CJEZMYDRYWKBOK-UHFFFAOYSA-N 0.000 claims description 3
- XWQCYQDOPREOJB-UHFFFAOYSA-N 2-[2-methyl-4-[1-[4-propan-2-yl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethoxy]phenoxy]acetic acid Chemical compound CC(C)C=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1C(C)OC1=CC=C(OCC(O)=O)C(C)=C1 XWQCYQDOPREOJB-UHFFFAOYSA-N 0.000 claims description 3
- OWDQZVUICOQNRV-UHFFFAOYSA-N 2-[2-methyl-4-[1-[4-propan-2-yl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethylsulfanyl]phenoxy]acetic acid Chemical compound CC(C)C=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1C(C)SC1=CC=C(OCC(O)=O)C(C)=C1 OWDQZVUICOQNRV-UHFFFAOYSA-N 0.000 claims description 3
- RMDYKBXFBHFGJV-QGZVFWFLSA-N 2-[4-[(1r)-1-[4-[2-(2-chloro-6-fluorophenyl)ethyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethyl]sulfanyl-2-methylphenoxy]acetic acid Chemical compound S([C@H](C)C1=C(N=C(S1)C=1C=CC(=CC=1)C(F)(F)F)CCC=1C(=CC=CC=1F)Cl)C1=CC=C(OCC(O)=O)C(C)=C1 RMDYKBXFBHFGJV-QGZVFWFLSA-N 0.000 claims description 3
- ZZYLGJYIVHRQFK-UHFFFAOYSA-N 2-[4-[1-[4-[2-(2-chloro-6-fluorophenyl)ethyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethoxy]-2-methylphenoxy]acetic acid Chemical compound S1C(C=2C=CC(=CC=2)C(F)(F)F)=NC(CCC=2C(=CC=CC=2F)Cl)=C1C(C)OC1=CC=C(OCC(O)=O)C(C)=C1 ZZYLGJYIVHRQFK-UHFFFAOYSA-N 0.000 claims description 3
- YUFHWCWFVMXCKR-UHFFFAOYSA-N 2-[4-[1-[4-[[3,5-bis(trifluoromethyl)phenoxy]methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethylsulfanyl]-2-methylphenoxy]acetic acid Chemical compound S1C(C=2C=CC(=CC=2)C(F)(F)F)=NC(COC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C1C(C)SC1=CC=C(OCC(O)=O)C(C)=C1 YUFHWCWFVMXCKR-UHFFFAOYSA-N 0.000 claims description 3
- FCLKUFWAJLXFFO-UHFFFAOYSA-N 2-[4-[1-[4-ethyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-5-yl]ethoxy]-2-methylphenoxy]acetic acid Chemical compound CCC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)OC=1C(C)OC1=CC=C(OCC(O)=O)C(C)=C1 FCLKUFWAJLXFFO-UHFFFAOYSA-N 0.000 claims description 3
- BVTYBSWFFUGGOH-RUZDIDTESA-N 3-[2-methyl-4-[(1r)-1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-5-yl]-2-phenylethoxy]phenyl]propanoic acid Chemical compound C([C@H](C=1OC(=NC=1C)C=1C=CC(=CC=1)C(F)(F)F)OC=1C=C(C)C(CCC(O)=O)=CC=1)C1=CC=CC=C1 BVTYBSWFFUGGOH-RUZDIDTESA-N 0.000 claims description 3
- MYPWXSGXJQAYEH-OAHLLOKOSA-N 3-[2-methyl-4-[(1r)-1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethoxy]phenyl]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(CCC(O)=O)C(C)=C1 MYPWXSGXJQAYEH-OAHLLOKOSA-N 0.000 claims description 3
- AWPKQIVBUIVRCN-INIZCTEOSA-N 3-[2-methyl-4-[(1s)-1-[4-propan-2-yl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethoxy]phenyl]propanoic acid Chemical compound O([C@@H](C)C=1SC(=NC=1C(C)C)C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(CCC(O)=O)C(C)=C1 AWPKQIVBUIVRCN-INIZCTEOSA-N 0.000 claims description 3
- BVFSSXGJVXHYQD-HNNXBMFYSA-N 3-[2-methyl-4-[(2r)-2-[5-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-4-yl]propyl]sulfanylphenyl]propanoic acid Chemical compound C([C@H](C)C1=C(SC(=N1)C=1C=CC(=CC=1)C(F)(F)F)C)SC1=CC=C(CCC(O)=O)C(C)=C1 BVFSSXGJVXHYQD-HNNXBMFYSA-N 0.000 claims description 3
- HRTBEAMEOCUEHU-UHFFFAOYSA-N 3-[2-methyl-4-[1-[2-(3-morpholin-4-ylphenyl)-4-propan-2-yl-1,3-oxazol-5-yl]ethoxy]phenyl]propanoic acid Chemical compound CC(C)C=1N=C(C=2C=C(C=CC=2)N2CCOCC2)OC=1C(C)OC1=CC=C(CCC(O)=O)C(C)=C1 HRTBEAMEOCUEHU-UHFFFAOYSA-N 0.000 claims description 3
- KTZLIPGEIYQWJU-UHFFFAOYSA-N 3-[2-methyl-4-[1-[2-(3-piperidin-1-ylphenyl)-4-propan-2-yl-1,3-oxazol-5-yl]ethoxy]phenyl]propanoic acid Chemical compound CC(C)C=1N=C(C=2C=C(C=CC=2)N2CCCCC2)OC=1C(C)OC1=CC=C(CCC(O)=O)C(C)=C1 KTZLIPGEIYQWJU-UHFFFAOYSA-N 0.000 claims description 3
- ZEFPIRIYJAPQPG-UHFFFAOYSA-N 3-[2-methyl-4-[1-[2-(4-piperidin-1-ylphenyl)-4-propan-2-yl-1,3-oxazol-5-yl]ethoxy]phenyl]propanoic acid Chemical compound CC(C)C=1N=C(C=2C=CC(=CC=2)N2CCCCC2)OC=1C(C)OC1=CC=C(CCC(O)=O)C(C)=C1 ZEFPIRIYJAPQPG-UHFFFAOYSA-N 0.000 claims description 3
- LDVIIFIFYVZYKG-UHFFFAOYSA-N 3-[2-methyl-4-[1-[4-(2-phenylethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethoxy]phenyl]propanoic acid Chemical compound S1C(C=2C=CC(=CC=2)C(F)(F)F)=NC(CCC=2C=CC=CC=2)=C1C(C)OC1=CC=C(CCC(O)=O)C(C)=C1 LDVIIFIFYVZYKG-UHFFFAOYSA-N 0.000 claims description 3
- KZCSYBFKHPXVLC-UHFFFAOYSA-N 3-[2-methyl-4-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-5-yl]pentoxy]phenyl]propanoic acid Chemical compound O1C(C=2C=CC(=CC=2)C(F)(F)F)=NC(C)=C1C(CCCC)OC1=CC=C(CCC(O)=O)C(C)=C1 KZCSYBFKHPXVLC-UHFFFAOYSA-N 0.000 claims description 3
- ULVMSXUCWAUANG-UHFFFAOYSA-N 3-[2-methyl-4-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-5-yl]propoxy]phenyl]propanoic acid Chemical compound O1C(C=2C=CC(=CC=2)C(F)(F)F)=NC(C)=C1C(CC)OC1=CC=C(CCC(O)=O)C(C)=C1 ULVMSXUCWAUANG-UHFFFAOYSA-N 0.000 claims description 3
- GYFJTUCUQQROME-UHFFFAOYSA-N 3-[2-methyl-4-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]-2-phenylethoxy]phenyl]propanoic acid Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1C(OC=1C=C(C)C(CCC(O)=O)=CC=1)CC1=CC=CC=C1 GYFJTUCUQQROME-UHFFFAOYSA-N 0.000 claims description 3
- MYPWXSGXJQAYEH-UHFFFAOYSA-N 3-[2-methyl-4-[1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethoxy]phenyl]propanoic acid Chemical compound S1C(C=2C=CC(=CC=2)C(F)(F)F)=NC(C)=C1C(C)OC1=CC=C(CCC(O)=O)C(C)=C1 MYPWXSGXJQAYEH-UHFFFAOYSA-N 0.000 claims description 3
- XFNTVTMUDBEFQP-UHFFFAOYSA-N 3-[2-methyl-4-[1-[4-phenyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethoxy]phenyl]propanoic acid Chemical compound S1C(C=2C=CC(=CC=2)C(F)(F)F)=NC(C=2C=CC=CC=2)=C1C(C)OC1=CC=C(CCC(O)=O)C(C)=C1 XFNTVTMUDBEFQP-UHFFFAOYSA-N 0.000 claims description 3
- LRSKXLDJOWWFSP-UHFFFAOYSA-N 3-[2-methyl-4-[1-[4-propan-2-yl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-5-yl]ethoxy]phenyl]propanoic acid Chemical compound CC(C)C=1N=C(C=2C=CC(=CC=2)C(F)(F)F)OC=1C(C)OC1=CC=C(CCC(O)=O)C(C)=C1 LRSKXLDJOWWFSP-UHFFFAOYSA-N 0.000 claims description 3
- AWPKQIVBUIVRCN-UHFFFAOYSA-N 3-[2-methyl-4-[1-[4-propan-2-yl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]ethoxy]phenyl]propanoic acid Chemical compound CC(C)C=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1C(C)OC1=CC=C(CCC(O)=O)C(C)=C1 AWPKQIVBUIVRCN-UHFFFAOYSA-N 0.000 claims description 3
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- 238000000338 in vitro Methods 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
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- OGLKSERFOPMWLR-UHFFFAOYSA-N methyl 2,2-dimethyl-3-oxopentanoate Chemical compound CCC(=O)C(C)(C)C(=O)OC OGLKSERFOPMWLR-UHFFFAOYSA-N 0.000 description 2
- AMDDOQIUPAINLH-UHFFFAOYSA-N methyl 2-(3-hydroxyphenyl)acetate Chemical compound COC(=O)CC1=CC=CC(O)=C1 AMDDOQIUPAINLH-UHFFFAOYSA-N 0.000 description 2
- DHYNFZGEMZIEIO-UHFFFAOYSA-N methyl 2-[2-(4-bromophenyl)-5-methyl-1,3-oxazol-4-yl]acetate Chemical compound O1C(C)=C(CC(=O)OC)N=C1C1=CC=C(Br)C=C1 DHYNFZGEMZIEIO-UHFFFAOYSA-N 0.000 description 2
- OYJIOMARRSXPCH-UHFFFAOYSA-N methyl 2-[2-(6-chloropyridin-3-yl)-5-methyl-1,3-oxazol-4-yl]acetate Chemical compound O1C(C)=C(CC(=O)OC)N=C1C1=CC=C(Cl)N=C1 OYJIOMARRSXPCH-UHFFFAOYSA-N 0.000 description 2
- YQKWPCOQXLSTAF-UHFFFAOYSA-N methyl 2-[5-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]propanoate Chemical compound O1C(C)=C(C(C)C(=O)OC)N=C1C1=CC=C(C(F)(F)F)C=C1 YQKWPCOQXLSTAF-UHFFFAOYSA-N 0.000 description 2
- SFOCIAVIILTCPM-UHFFFAOYSA-N methyl 2-methyl-2-[5-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]propanoate Chemical compound O1C(C)=C(C(C)(C)C(=O)OC)N=C1C1=CC=C(C(F)(F)F)C=C1 SFOCIAVIILTCPM-UHFFFAOYSA-N 0.000 description 2
- CFZLIDDGVAVFLM-UHFFFAOYSA-N methyl 2-methyl-2-[5-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-4-yl]propanoate Chemical compound S1C(C)=C(C(C)(C)C(=O)OC)N=C1C1=CC=C(C(F)(F)F)C=C1 CFZLIDDGVAVFLM-UHFFFAOYSA-N 0.000 description 2
- AVNZOGNVFGETNQ-UHFFFAOYSA-N methyl 2-methyl-3-oxopentanoate Chemical compound CCC(=O)C(C)C(=O)OC AVNZOGNVFGETNQ-UHFFFAOYSA-N 0.000 description 2
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- PFUCHFQQAZBFDR-UHFFFAOYSA-N methyl 3-(4-amino-2-methylphenyl)propanoate Chemical compound COC(=O)CCC1=CC=C(N)C=C1C PFUCHFQQAZBFDR-UHFFFAOYSA-N 0.000 description 2
- HVVMSAIGSLGZCS-UHFFFAOYSA-N methyl 3-[(4-bromobenzoyl)amino]-4-oxopentanoate Chemical compound COC(=O)CC(C(C)=O)NC(=O)C1=CC=C(Br)C=C1 HVVMSAIGSLGZCS-UHFFFAOYSA-N 0.000 description 2
- RINRGCNMBFHEMJ-UHFFFAOYSA-N methyl 3-[(6-chloropyridine-3-carbonyl)amino]-4-oxopentanoate Chemical compound COC(=O)CC(C(C)=O)NC(=O)C1=CC=C(Cl)N=C1 RINRGCNMBFHEMJ-UHFFFAOYSA-N 0.000 description 2
- IVVKJOHAKNPIEU-UHFFFAOYSA-N methyl 3-[2-methyl-4-[2-[5-methyl-2-(4-pyridin-2-ylphenyl)-1,3-oxazol-4-yl]propoxy]phenyl]propanoate Chemical compound C1=C(C)C(CCC(=O)OC)=CC=C1OCC(C)C1=C(C)OC(C=2C=CC(=CC=2)C=2N=CC=CC=2)=N1 IVVKJOHAKNPIEU-UHFFFAOYSA-N 0.000 description 2
- UKFAWRFNJGQYHV-UHFFFAOYSA-N methyl 3-[4-[1-[2-(4-bromophenyl)-4-propan-2-yl-1,3-oxazol-5-yl]ethoxy]-2-methylphenyl]propanoate Chemical compound C1=C(C)C(CCC(=O)OC)=CC=C1OC(C)C1=C(C(C)C)N=C(C=2C=CC(Br)=CC=2)O1 UKFAWRFNJGQYHV-UHFFFAOYSA-N 0.000 description 2
- XOEYEQKHXMESFA-UHFFFAOYSA-N methyl 3-[4-[1-[4-ethyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-5-yl]ethoxy]-2-methylphenyl]propanoate Chemical compound CCC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)OC=1C(C)OC1=CC=C(CCC(=O)OC)C(C)=C1 XOEYEQKHXMESFA-UHFFFAOYSA-N 0.000 description 2
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
- 229960001641 troglitazone Drugs 0.000 description 1
- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/26—Radicals substituted by sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Diabetes (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Medicinal Preparation (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35980802P | 2002-02-25 | 2002-02-25 | |
| US359808P | 2002-02-25 | ||
| PCT/US2003/002679 WO2003072100A1 (en) | 2002-02-25 | 2003-02-13 | Peroxisome proliferator activated receptor modulators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60315603D1 DE60315603D1 (de) | 2007-09-27 |
| DE60315603T2 true DE60315603T2 (de) | 2008-05-21 |
Family
ID=27766138
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60315603T Expired - Fee Related DE60315603T2 (de) | 2002-02-25 | 2003-02-13 | Modulatoren von peroxisome proliferator-aktivierten rezeptoren |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7153878B2 (enExample) |
| EP (1) | EP1480640B1 (enExample) |
| JP (1) | JP2005529077A (enExample) |
| AT (1) | ATE369855T1 (enExample) |
| AU (1) | AU2003217274A1 (enExample) |
| DE (1) | DE60315603T2 (enExample) |
| ES (1) | ES2290439T3 (enExample) |
| WO (1) | WO2003072100A1 (enExample) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040072838A1 (en) * | 2000-12-20 | 2004-04-15 | Pierette Banker | Thiazole and oxazole derivatives as activators of human peroxisome proliferator activated receptors |
| US7105551B2 (en) * | 2000-12-20 | 2006-09-12 | Smithkline Beecham Corporation | Thiazole derivatives for treating PPAR related disorders |
| JP2005529077A (ja) | 2002-02-25 | 2005-09-29 | イーライ・リリー・アンド・カンパニー | ペルオキシソーム増殖因子活性化受容体調節物質 |
| JP2006527175A (ja) | 2003-06-06 | 2006-11-30 | エフ.ホフマン−ラ ロシュ アーゲー | アニリン誘導体 |
| US7560475B2 (en) * | 2003-09-22 | 2009-07-14 | Ono Pharmaceutical Co., Ltd. | Phenylacetic acid derivative, process for producing the same, and use |
| BRPI0416284A (pt) * | 2003-11-05 | 2007-01-23 | Hoffmann La Roche | compostos, processo para a manufatura dos mesmos, composições farmacêuticas que os contêm, método para o tratamento e/ou prevenção de enfermidades que são moduladas por agonistas ppar(delta) e/ou ppar(alfa) e sua utilização |
| JP4745244B2 (ja) * | 2003-11-05 | 2011-08-10 | エフ.ホフマン−ラ ロシュ アーゲー | Pparアゴニストとしてのフェニル誘導体 |
| WO2005060958A1 (en) * | 2003-12-19 | 2005-07-07 | Kalypsys, Inc. | (5- (2-phenyl)-thiazol-5-ylmethoxy)-indol-1-yl) -acetic acid derivatives and related compounds as modulators of the human ppar-delta receptor for the treatment of metabolic disorders such as type 2 diabetes |
| WO2005087710A1 (ja) * | 2004-03-15 | 2005-09-22 | Takeda Pharmaceutical Company Limited | アミノフェニルプロパン酸誘導体 |
| EP1745014B1 (en) | 2004-05-05 | 2011-07-06 | High Point Pharmaceuticals, LLC | Novel compounds, their preparation and use |
| WO2005105726A1 (en) | 2004-05-05 | 2005-11-10 | Novo Nordisk A/S | Novel compounds, their preparation and use |
| DE102004040736B4 (de) * | 2004-08-23 | 2007-01-11 | Sanofi-Aventis Deutschland Gmbh | Verfahren zur Herstellung von Diarylcycloalkylderivaten |
| WO2006091047A1 (en) | 2005-02-25 | 2006-08-31 | Heonjoong Kang | Thiazole derivatives as ppar delta ligands and their manufacturing process |
| US20090054493A1 (en) * | 2005-02-25 | 2009-02-26 | Heonjoong Kang Kang | Thiazole derivatives as ppar delta ligands and their manufacturing process |
| EP2298742B1 (en) | 2005-06-30 | 2014-01-08 | High Point Pharmaceuticals, LLC | phenoxy acetic acids as PPAR delta activators |
| WO2007039172A1 (en) * | 2005-09-29 | 2007-04-12 | Sanofi-Aventis | Phenyl- and pyridyl-i, 2 , 4 -oxadiazolone derivatives with phenyl group, processes for their preparation and their use as pharmaceuticals |
| EP2386540A1 (en) | 2005-12-22 | 2011-11-16 | High Point Pharmaceuticals, LLC | Novel compounds, their preparation and use |
| EP1999119A2 (en) | 2006-02-15 | 2008-12-10 | Abbott Laboratories | Novel acetyl-coa carboxylase (acc) inhibitors and their use in diabetes, obesity and metabolic syndrome |
| CA2641766A1 (en) | 2006-02-15 | 2007-08-23 | Abbott Laboratories | Novel acetyl-coa carboxylase (acc) inhibitors and their use in diabetes, obesity and metabolic syndrome |
| CA2645719A1 (en) | 2006-03-09 | 2007-09-13 | High Point Pharmaceuticals, Llc | Compounds that modulate ppar activity, their preparation and use |
| AU2007239283B2 (en) * | 2006-04-18 | 2013-02-07 | Nippon Chemiphar Co., Ltd. | Activating agent for peroxisome proliferator activated receptor delta |
| WO2008066356A1 (en) | 2006-12-02 | 2008-06-05 | Seoul National University Industry Foundation | Aryl compounds as ppar ligands and their use |
| US8236831B2 (en) | 2007-01-08 | 2012-08-07 | Seoul National University Industry Foundation | Thiazole compound (as PPARδ) ligand and pharmaceutical, cosmetic and health food comprised thereof |
| WO2008154023A1 (en) * | 2007-06-11 | 2008-12-18 | Cerenis Therapeutics S.A. | Novel uses of ppar delta agonists |
| CA2741125A1 (en) | 2008-10-22 | 2010-04-29 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| CN102271509A (zh) | 2008-10-31 | 2011-12-07 | 默沙东公司 | 用于抗糖尿病药的新型环苯并咪唑衍生物 |
| AU2011218830B2 (en) | 2010-02-25 | 2014-07-24 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| CA2789458A1 (en) * | 2010-02-25 | 2011-09-01 | Heonjoong Kang | Selenalzole derivative having ligand which activates peroxisome proliferator activated receptor (ppar), preparing method thereof and usage of the chemical compounds |
| BR112013004882A2 (pt) | 2010-08-31 | 2016-05-03 | Snu R&Db Foundation | utilização de reprogramação fetal de agonista ppar delta |
| KR101668514B1 (ko) | 2011-02-25 | 2016-10-21 | 머크 샤프 앤드 돔 코포레이션 | 항당뇨병제로서 유용한 신규 시클릭 아자벤즈이미다졸 유도체 |
| US9688673B2 (en) | 2011-03-08 | 2017-06-27 | The Regents Of The University Of California | Deoxycytidine kinase binding compounds |
| EP2880028B1 (en) | 2012-08-02 | 2020-09-30 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| US20150307459A1 (en) | 2012-11-27 | 2015-10-29 | Basf Se | Substituted 2-[phenoxy-phenyl]-1-[1,2,4]triazol-1-yl-ethanol Compounds and Their Use as Fungicides |
| US20150313229A1 (en) | 2012-11-27 | 2015-11-05 | Basf Se | Substituted [1,2,4] Triazole Compounds |
| EP2928873A1 (en) | 2012-11-27 | 2015-10-14 | Basf Se | Substituted 2-[phenoxy-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds and their use as fungicides |
| CN104994848A (zh) | 2013-02-22 | 2015-10-21 | 默沙东公司 | 抗糖尿病二环化合物 |
| WO2014139388A1 (en) | 2013-03-14 | 2014-09-18 | Merck Sharp & Dohme Corp. | Novel indole derivatives useful as anti-diabetic agents |
| WO2015035171A1 (en) | 2013-09-09 | 2015-03-12 | High Point Pharmaceuticals, Llc | Use of a ppar-delta agonist for treating muscle atrophy |
| WO2015051496A1 (en) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| CN106456614A (zh) | 2014-03-14 | 2017-02-22 | 爱尔皮奥治疗有限公司 | HPTP‑β抑制剂 |
| AR100743A1 (es) | 2014-06-06 | 2016-10-26 | Basf Se | Compuestos de [1,2,4]triazol sustituido |
| US11072602B2 (en) | 2016-12-06 | 2021-07-27 | Merck Sharp & Dohme Corp. | Antidiabetic heterocyclic compounds |
| EP3558298A4 (en) | 2016-12-20 | 2020-08-05 | Merck Sharp & Dohme Corp. | ANTIDIABETIC SPIROCHROMAN COMPOUNDS |
| CN109897013B (zh) * | 2019-03-31 | 2023-04-07 | 无锡科华生物科技有限公司 | 一种选择性PPARδ激动剂GW501516的制备方法 |
| US11634387B2 (en) | 2019-09-26 | 2023-04-25 | Abionyx Pharma Sa | Compounds useful for treating liver diseases |
| CN113912547B (zh) | 2020-07-10 | 2024-04-30 | 成都凡诺西生物医药科技有限公司 | 取代苯丙咪唑类衍生物及其应用 |
| AU2021368138A1 (en) | 2020-11-02 | 2023-06-22 | Trethera Corporation | Crystalline forms of a deoxycytidine kinase inhibitor and uses thereof |
| WO2022189856A1 (en) * | 2021-03-08 | 2022-09-15 | Abionyx Pharma Sa | Compounds useful for treating liver diseases |
| WO2023147309A1 (en) | 2022-01-25 | 2023-08-03 | Reneo Pharmaceuticals, Inc. | Use of ppar-delta agonists in the treatment of disease |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20000068151A (ko) * | 1996-08-19 | 2000-11-25 | 미즈노 마사루 | 프로피온산 유도체 및 그의 용도 |
| GB9914977D0 (en) | 1999-06-25 | 1999-08-25 | Glaxo Group Ltd | Chemical compounds |
| EP1310494B1 (en) * | 2000-08-11 | 2012-01-25 | Nippon Chemiphar Co., Ltd. | PPAR (delta) ACTIVATORS |
| WO2002018355A1 (en) * | 2000-08-23 | 2002-03-07 | Eli Lilly And Company | Oxazolyl-aryloxyacetic acid derivatives and their use as ppar agonists |
| GB0031107D0 (en) | 2000-12-20 | 2001-01-31 | Glaxo Group Ltd | Chemical compounds |
| JP2005529077A (ja) | 2002-02-25 | 2005-09-29 | イーライ・リリー・アンド・カンパニー | ペルオキシソーム増殖因子活性化受容体調節物質 |
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- 2003-02-13 JP JP2003570846A patent/JP2005529077A/ja active Pending
- 2003-02-13 AT AT03713316T patent/ATE369855T1/de not_active IP Right Cessation
- 2003-02-13 ES ES03713316T patent/ES2290439T3/es not_active Expired - Lifetime
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- 2003-02-13 EP EP03713316A patent/EP1480640B1/en not_active Expired - Lifetime
- 2003-02-13 WO PCT/US2003/002679 patent/WO2003072100A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| DE60315603D1 (de) | 2007-09-27 |
| US7153878B2 (en) | 2006-12-26 |
| EP1480640B1 (en) | 2007-08-15 |
| US20050107449A1 (en) | 2005-05-19 |
| ES2290439T3 (es) | 2008-02-16 |
| ATE369855T1 (de) | 2007-09-15 |
| EP1480640A1 (en) | 2004-12-01 |
| JP2005529077A (ja) | 2005-09-29 |
| WO2003072100A1 (en) | 2003-09-04 |
| AU2003217274A1 (en) | 2003-09-09 |
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