CA2418134A1 - Oxazolyl-arylpropionic acid derivatives and their use as ppar agonists - Google Patents

Info

Publication number

CA2418134A1

CA2418134A1 CA002418134A CA2418134A CA2418134A1 CA 2418134 A1 CA2418134 A1 CA 2418134A1 CA 002418134 A CA002418134 A CA 002418134A CA 2418134 A CA2418134 A CA 2418134A CA 2418134 A1 CA2418134 A1 CA 2418134A1

Authority

CA

Canada

Prior art keywords

methyl

phenyl

oxazol

ethoxy

alkyl

Prior art date

2000-08-23

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
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• 239000002253 acid Substances 0.000 title claims description 18
• 101150014691 PPARA gene Proteins 0.000 title description 10
• 239000000556 agonist Substances 0.000 title description 6
• 150000001875 compounds Chemical class 0.000 claims abstract description 188
• 238000000034 method Methods 0.000 claims abstract description 57
• 150000003839 salts Chemical class 0.000 claims abstract description 46
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 26
• 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims abstract description 23
• 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims abstract description 23
• 239000012453 solvate Substances 0.000 claims abstract description 17
• 150000004677 hydrates Chemical class 0.000 claims abstract description 16
• -1 1,2,3,4-tetrahydronaphthyl Chemical group 0.000 claims description 96
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 83
• 125000003118 aryl group Chemical group 0.000 claims description 70
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 67
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 66
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 56
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 55
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 47
• 125000001475 halogen functional group Chemical group 0.000 claims description 45
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 39
• 125000001072 heteroaryl group Chemical group 0.000 claims description 37
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 30
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 29
• 239000008103 glucose Substances 0.000 claims description 29
• 229910000029 sodium carbonate Inorganic materials 0.000 claims description 20
• 238000011282 treatment Methods 0.000 claims description 20
• 241000124008 Mammalia Species 0.000 claims description 19
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 18
• 229910000024 caesium carbonate Inorganic materials 0.000 claims description 18
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
• 239000002585 base Substances 0.000 claims description 16
• 125000000623 heterocyclic group Chemical group 0.000 claims description 16
• 125000001624 naphthyl group Chemical group 0.000 claims description 16
• 102000005962 receptors Human genes 0.000 claims description 16
• 108020003175 receptors Proteins 0.000 claims description 16
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 16
• 150000003626 triacylglycerols Chemical class 0.000 claims description 14
• 210000002966 serum Anatomy 0.000 claims description 13
• BUTJKZPBLVEJNL-UHFFFAOYSA-N 2-(3,4-dimethylphenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(C)C(C)=C1 BUTJKZPBLVEJNL-UHFFFAOYSA-N 0.000 claims description 12
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 12
• 210000004369 blood Anatomy 0.000 claims description 12
• 239000008280 blood Substances 0.000 claims description 12
• 206010012601 diabetes mellitus Diseases 0.000 claims description 12
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
• 125000000217 alkyl group Chemical group 0.000 claims description 11
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 11
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 9
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 9
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 9
• WGZHWUKBNXYGQV-UHFFFAOYSA-N 2-methyl-3-[4-[2-[5-methyl-2-(4-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]-2-[4-(trifluoromethoxy)phenoxy]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(OC(F)(F)F)C=C1 WGZHWUKBNXYGQV-UHFFFAOYSA-N 0.000 claims description 8
• 208000011580 syndromic disease Diseases 0.000 claims description 8
• IWPWLTHKDQSYRC-UHFFFAOYSA-N 2-(4-chlorophenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(Cl)C=C1 IWPWLTHKDQSYRC-UHFFFAOYSA-N 0.000 claims description 7
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 7
• 108010007622 LDL Lipoproteins Proteins 0.000 claims description 7
• 102000007330 LDL Lipoproteins Human genes 0.000 claims description 7
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 7
• IYSUFUOZVISENV-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yloxy)-2-methyl-3-[4-[2-[5-methyl-2-(3-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound N=1C(CCOC=2C=CC(CC(C)(OC=3C=C4OCOC4=CC=3)C(O)=O)=CC=2)=C(C)OC=1C(C=1)=CC=CC=1C1=CC=CC=C1 IYSUFUOZVISENV-UHFFFAOYSA-N 0.000 claims description 6
• WYBYEEFGPCCUJQ-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yloxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound N=1C(CCOC=2C=CC(CC(C)(OC=3C=C4OCOC4=CC=3)C(O)=O)=CC=2)=C(C)OC=1C(C=C1)=CC=C1C1=CC=CC=C1 WYBYEEFGPCCUJQ-UHFFFAOYSA-N 0.000 claims description 6
• QRYBMPWFECZDOK-UHFFFAOYSA-N 2-(2-fluorophenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC=C1F QRYBMPWFECZDOK-UHFFFAOYSA-N 0.000 claims description 6
• HUYITJFINCZYLA-UHFFFAOYSA-N 2-(3,4-difluorophenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(F)C(F)=C1 HUYITJFINCZYLA-UHFFFAOYSA-N 0.000 claims description 6
• BRTCMAARHAQWKO-UHFFFAOYSA-N 2-(3,4-difluorophenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(F)C(F)=C1 BRTCMAARHAQWKO-UHFFFAOYSA-N 0.000 claims description 6
• XCMWTYWPVHKIAX-UHFFFAOYSA-N 2-(3,4-dimethylphenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(C)C(C)=C1 XCMWTYWPVHKIAX-UHFFFAOYSA-N 0.000 claims description 6
• BOZAAQICFMIWTE-UHFFFAOYSA-N 2-(4-fluorophenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(F)C=C1 BOZAAQICFMIWTE-UHFFFAOYSA-N 0.000 claims description 6
• HAKDKTDSJACAOA-UHFFFAOYSA-N 2-(4-fluorophenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(F)C=C1 HAKDKTDSJACAOA-UHFFFAOYSA-N 0.000 claims description 6
• UBIXGNKRQAIXQL-UHFFFAOYSA-N 2-[[4-[2-[5-methyl-2-(3-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]methyl]-2-phenoxyhexanoic acid Chemical compound C=1C=CC=CC=1OC(C(O)=O)(CCCC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C(C=1)=CC=CC=1C1=CC=CC=C1 UBIXGNKRQAIXQL-UHFFFAOYSA-N 0.000 claims description 6
• XEBAZFCWDSVERF-UHFFFAOYSA-N 2-[[4-[2-[5-methyl-2-(4-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]methyl]-2-phenoxyhexanoic acid Chemical compound C=1C=CC=CC=1OC(C(O)=O)(CCCC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C(C=C1)=CC=C1C1=CC=CC=C1 XEBAZFCWDSVERF-UHFFFAOYSA-N 0.000 claims description 6
• LAQQWWJAYLBUGN-UHFFFAOYSA-N 2-methyl-2-(3-methylphenoxy)-3-[4-[2-[5-methyl-2-(4-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC(C)=C1 LAQQWWJAYLBUGN-UHFFFAOYSA-N 0.000 claims description 6
• OSOCRAKEOIFNIR-UHFFFAOYSA-N 2-methyl-3-[4-[2-[5-methyl-2-(4-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]-2-[3-(trifluoromethyl)phenoxy]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC(C(F)(F)F)=C1 OSOCRAKEOIFNIR-UHFFFAOYSA-N 0.000 claims description 6
• ARIJJRAOPWDBMS-UHFFFAOYSA-N 2-methyl-3-[4-[2-[5-methyl-2-(4-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]-2-[4-(trifluoromethoxy)phenoxy]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(OC(F)(F)F)C=C1 ARIJJRAOPWDBMS-UHFFFAOYSA-N 0.000 claims description 6
• 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 6
• 150000001543 aryl boronic acids Chemical class 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• SWADNQWYDSAALT-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yloxy)-2-methyl-3-[4-[2-[5-methyl-2-(3-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound N=1C(CCOC=2C=CC(CC(C)(OC=3C=C4OCOC4=CC=3)C(O)=O)=CC=2)=C(C)OC=1C(C=1)=CC=CC=1C1=CC=CS1 SWADNQWYDSAALT-UHFFFAOYSA-N 0.000 claims description 5
• CZFLATZIUAZOQD-UHFFFAOYSA-N 2-(3,4-difluorophenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(3-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=C(C=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(F)C(F)=C1 CZFLATZIUAZOQD-UHFFFAOYSA-N 0.000 claims description 5
• OGZVZINWQSIAGE-UHFFFAOYSA-N 2-(3-fluorophenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC(F)=C1 OGZVZINWQSIAGE-UHFFFAOYSA-N 0.000 claims description 5
• FWHLXGIACRDWAA-UHFFFAOYSA-N 2-(3-fluorophenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC(F)=C1 FWHLXGIACRDWAA-UHFFFAOYSA-N 0.000 claims description 5
• OSCFHDZVHVHBFJ-UHFFFAOYSA-N 2-(3-methoxyphenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound COC1=CC=CC(OC(C)(CC=2C=CC(OCCC3=C(OC(=N3)C=3C=CC(=CC=3)C=3C=CC=CC=3)C)=CC=2)C(O)=O)=C1 OSCFHDZVHVHBFJ-UHFFFAOYSA-N 0.000 claims description 5
• SRDVWJUOPXZFNK-UHFFFAOYSA-N 2-(3-methoxyphenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound COC1=CC=CC(OC(C)(CC=2C=CC(OCCC3=C(OC(=N3)C=3C=CC(=CC=3)C=3SC=CC=3)C)=CC=2)C(O)=O)=C1 SRDVWJUOPXZFNK-UHFFFAOYSA-N 0.000 claims description 5
• ZIPDTULWNLDTGL-UHFFFAOYSA-N 2-(4-chlorophenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(3-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=C(C=CC=2)C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(Cl)C=C1 ZIPDTULWNLDTGL-UHFFFAOYSA-N 0.000 claims description 5
• LTPUWBBEPNBCSK-UHFFFAOYSA-N 2-(4-cyclohexylphenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(3-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=C(C=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC(C=C1)=CC=C1C1CCCCC1 LTPUWBBEPNBCSK-UHFFFAOYSA-N 0.000 claims description 5
• MROJJKRXUSSSTL-UHFFFAOYSA-N 2-(4-cyclohexylphenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC(C=C1)=CC=C1C1CCCCC1 MROJJKRXUSSSTL-UHFFFAOYSA-N 0.000 claims description 5
• FRVNFDUZXBYFTE-UHFFFAOYSA-N 2-[[4-[2-[5-methyl-2-(4-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]methyl]-2-phenoxybutanoic acid Chemical compound C=1C=CC=CC=1OC(C(O)=O)(CC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C(C=C1)=CC=C1C1=CC=CC=C1 FRVNFDUZXBYFTE-UHFFFAOYSA-N 0.000 claims description 5
• AKMKLBMKLLQGBK-UHFFFAOYSA-N 2-methyl-2-(3-methylphenoxy)-3-[4-[2-[5-methyl-2-(3-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=C(C=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC(C)=C1 AKMKLBMKLLQGBK-UHFFFAOYSA-N 0.000 claims description 5
• NTPWLXYSCVDGHT-UHFFFAOYSA-N 2-methyl-2-(3-methylphenoxy)-3-[4-[2-[5-methyl-2-(4-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC(C)=C1 NTPWLXYSCVDGHT-UHFFFAOYSA-N 0.000 claims description 5
• UMUZXAUEVJEFEJ-UHFFFAOYSA-N 2-methyl-3-[4-[2-[5-methyl-2-(3-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]-3-propylphenyl]-2-phenoxypropanoic acid Chemical compound C=1C=C(OCCC2=C(OC(=N2)C=2C=C(C=CC=2)C=2C=CC=CC=2)C)C(CCC)=CC=1CC(C)(C(O)=O)OC1=CC=CC=C1 UMUZXAUEVJEFEJ-UHFFFAOYSA-N 0.000 claims description 5
• JKUYHUMOGXWLCU-UHFFFAOYSA-N 2-methyl-3-[4-[2-[5-methyl-2-(3-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]-2-phenoxypropanoic acid Chemical compound CC=1OC(C=2C=C(C=CC=2)C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC=C1 JKUYHUMOGXWLCU-UHFFFAOYSA-N 0.000 claims description 5
• RIXXENNLVMJOJD-UHFFFAOYSA-N 2-methyl-3-[4-[2-[5-methyl-2-(3-thiophen-3-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]-2-phenoxypropanoic acid Chemical compound CC=1OC(C=2C=C(C=CC=2)C2=CSC=C2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC=C1 RIXXENNLVMJOJD-UHFFFAOYSA-N 0.000 claims description 5
• UYHJZSKFRUDZLC-UHFFFAOYSA-N 2-methyl-3-[4-[2-[5-methyl-2-(4-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]-2-[4-(trifluoromethyl)phenoxy]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(C(F)(F)F)C=C1 UYHJZSKFRUDZLC-UHFFFAOYSA-N 0.000 claims description 5
• OUDVQFHXCHLCBP-UHFFFAOYSA-N 3-[4-[2-[2-[3-(4-fluorophenyl)phenyl]-5-methyl-1,3-oxazol-4-yl]ethoxy]phenyl]-2-methyl-2-phenoxypropanoic acid Chemical compound CC=1OC(C=2C=C(C=CC=2)C=2C=CC(F)=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC=C1 OUDVQFHXCHLCBP-UHFFFAOYSA-N 0.000 claims description 5
• 108010010234 HDL Lipoproteins Proteins 0.000 claims description 5
• 102000015779 HDL Lipoproteins Human genes 0.000 claims description 5
• 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 5
• 150000008041 alkali metal carbonates Chemical class 0.000 claims description 5
• WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 5
• AZNAZJIOOIFBAI-UHFFFAOYSA-N 2-(3-fluorophenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(3-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=C(C=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC(F)=C1 AZNAZJIOOIFBAI-UHFFFAOYSA-N 0.000 claims description 4
• HVBYJDCQVVOJCA-UHFFFAOYSA-N 2-(3-methoxyphenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(3-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound COC1=CC=CC(OC(C)(CC=2C=CC(OCCC3=C(OC(=N3)C=3C=C(C=CC=3)C=3C=CC=CC=3)C)=CC=2)C(O)=O)=C1 HVBYJDCQVVOJCA-UHFFFAOYSA-N 0.000 claims description 4
• AGXLJFIKDPNOSP-UHFFFAOYSA-N 2-(3-tert-butylphenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(4-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC(C(C)(C)C)=C1 AGXLJFIKDPNOSP-UHFFFAOYSA-N 0.000 claims description 4
• UNBMYBLYWTUOST-UHFFFAOYSA-N 2-(4-chlorophenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(3-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=C(C=CC=2)C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(Cl)C=C1 UNBMYBLYWTUOST-UHFFFAOYSA-N 0.000 claims description 4
• GJYSQPFITVPKRL-UHFFFAOYSA-N 2-(4-cyclohexylphenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(3-thiophen-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=C(C=CC=2)C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC(C=C1)=CC=C1C1CCCCC1 GJYSQPFITVPKRL-UHFFFAOYSA-N 0.000 claims description 4
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• CTSUQBKLKYJCJL-UHFFFAOYSA-N ethyl 2-[(4-hydroxyphenyl)methyl]-2-phenoxybutanoate;ethyl 2-phenoxy-2-[(4-phenylmethoxyphenyl)methyl]butanoate Chemical compound C=1C=CC=CC=1OC(CC)(C(=O)OCC)CC1=CC=C(O)C=C1.C=1C=CC=CC=1OC(CC)(C(=O)OCC)CC(C=C1)=CC=C1OCC1=CC=CC=C1 CTSUQBKLKYJCJL-UHFFFAOYSA-N 0.000 description 1
• UIOPFTQQCQTAJN-UHFFFAOYSA-N ethyl 2-[(4-hydroxyphenyl)methyl]-2-phenoxyhexanoate;ethyl 2-phenoxy-2-[(4-phenylmethoxyphenyl)methyl]-3-(2,2,2-trifluoroacetyl)oxyhexanoate Chemical compound C=1C=CC=CC=1OC(C(=O)OCC)(CCCC)CC1=CC=C(O)C=C1.C=1C=CC=CC=1OC(C(=O)OCC)(C(OC(=O)C(F)(F)F)CCC)CC(C=C1)=CC=C1OCC1=CC=CC=C1 UIOPFTQQCQTAJN-UHFFFAOYSA-N 0.000 description 1
• MHHPLJDSWJLCBU-UHFFFAOYSA-N ethyl 2-[3-(trifluoromethyl)phenoxy]propanoate Chemical compound CCOC(=O)C(C)OC1=CC=CC(C(F)(F)F)=C1 MHHPLJDSWJLCBU-UHFFFAOYSA-N 0.000 description 1
• SVMJFQZYTMJDRT-UHFFFAOYSA-N ethyl 2-[3-(trifluoromethyl)phenoxy]propanoate;3-(trifluoromethyl)phenol Chemical compound OC1=CC=CC(C(F)(F)F)=C1.CCOC(=O)C(C)OC1=CC=CC(C(F)(F)F)=C1 SVMJFQZYTMJDRT-UHFFFAOYSA-N 0.000 description 1
• VNMRLWCWQJUHGZ-UHFFFAOYSA-N ethyl 2-[4-(trifluoromethoxy)phenoxy]propanoate Chemical compound CCOC(=O)C(C)OC1=CC=C(OC(F)(F)F)C=C1 VNMRLWCWQJUHGZ-UHFFFAOYSA-N 0.000 description 1
• HWUTXRMOPBTVIA-UHFFFAOYSA-N ethyl 2-[4-(trifluoromethoxy)phenoxy]propanoate 4-(trifluoromethoxy)phenol Chemical compound FC(OC1=CC=C(C=C1)O)(F)F.C(C)OC(C(C)OC1=CC=C(C=C1)OC(F)(F)F)=O HWUTXRMOPBTVIA-UHFFFAOYSA-N 0.000 description 1
• BRSNOFNEGYMYKW-UHFFFAOYSA-N ethyl 2-[4-(trifluoromethyl)phenoxy]propanoate Chemical compound CCOC(=O)C(C)OC1=CC=C(C(F)(F)F)C=C1 BRSNOFNEGYMYKW-UHFFFAOYSA-N 0.000 description 1
• UUCUWXICPLNEBB-UHFFFAOYSA-N ethyl 2-[4-(trifluoromethyl)phenoxy]propanoate 4-(trifluoromethyl)phenol Chemical compound FC(C1=CC=C(C=C1)O)(F)F.C(C)OC(C(C)OC1=CC=C(C=C1)C(F)(F)F)=O UUCUWXICPLNEBB-UHFFFAOYSA-N 0.000 description 1
• XIMFCGSNSKXPBO-UHFFFAOYSA-N ethyl 2-bromobutanoate Chemical compound CCOC(=O)C(Br)CC XIMFCGSNSKXPBO-UHFFFAOYSA-N 0.000 description 1
• KSBUFFBSHVFVPJ-UHFFFAOYSA-N ethyl 2-methyl-2-phenoxy-3-(4-phenylmethoxynaphthalen-1-yl)propanoate Chemical compound C=1C=CC=CC=1OC(C)(C(=O)OCC)CC(C1=CC=CC=C11)=CC=C1OCC1=CC=CC=C1 KSBUFFBSHVFVPJ-UHFFFAOYSA-N 0.000 description 1
• YNPUGZZMBLXSRC-UHFFFAOYSA-N ethyl 2-methyl-3-[4-[2-[5-methyl-2-(3-thiophen-3-ylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]-2-phenoxypropanoate Chemical compound C=1C=CC=CC=1OC(C)(C(=O)OCC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C(C=1)=CC=CC=1C=1C=CSC=1 YNPUGZZMBLXSRC-UHFFFAOYSA-N 0.000 description 1
• SGKGBGFCUCHARM-UHFFFAOYSA-N ethyl 2-methyl-3-[4-[2-[5-methyl-2-(4-phenylphenyl)-1,3-oxazol-4-yl]ethoxy]phenyl]-2-phenoxypropanoate Chemical compound C=1C=CC=CC=1OC(C)(C(=O)OCC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C(C=C1)=CC=C1C1=CC=CC=C1 SGKGBGFCUCHARM-UHFFFAOYSA-N 0.000 description 1
• XMSXBKFQIRYRMD-UHFFFAOYSA-N ethyl 2-methyl-3-naphthalen-1-yl-2-phenoxypropanoate;ethyl 2-methyl-2-phenoxy-3-(4-phenylmethoxynaphthalen-1-yl)propanoate Chemical compound C=1C=CC2=CC=CC=C2C=1CC(C)(C(=O)OCC)OC1=CC=CC=C1.C=1C=CC=CC=1OC(C)(C(=O)OCC)CC(C1=CC=CC=C11)=CC=C1OCC1=CC=CC=C1 XMSXBKFQIRYRMD-UHFFFAOYSA-N 0.000 description 1
• IHASFDBVENKSHI-UHFFFAOYSA-N ethyl 2-phenoxybutanoate Chemical compound CCOC(=O)C(CC)OC1=CC=CC=C1 IHASFDBVENKSHI-UHFFFAOYSA-N 0.000 description 1
• QRFZJOXTFXKLGB-UHFFFAOYSA-N ethyl 2-phenoxyhexanoate Chemical compound CCCCC(C(=O)OCC)OC1=CC=CC=C1 QRFZJOXTFXKLGB-UHFFFAOYSA-N 0.000 description 1
• QKEXRNJCFDGBNV-UHFFFAOYSA-N ethyl 3-(4-hydroxy-3-prop-2-enylphenyl)-2-methyl-2-phenoxypropanoate Chemical compound C=1C=CC=CC=1OC(C)(C(=O)OCC)CC1=CC=C(O)C(CC=C)=C1 QKEXRNJCFDGBNV-UHFFFAOYSA-N 0.000 description 1
• MGZWVUCOTBYLAP-UHFFFAOYSA-N ethyl 3-(4-hydroxyphenyl)-2-(3-methoxyphenoxy)-2-methylpropanoate Chemical compound C=1C=CC(OC)=CC=1OC(C)(C(=O)OCC)CC1=CC=C(O)C=C1 MGZWVUCOTBYLAP-UHFFFAOYSA-N 0.000 description 1
• ZVDYEIHGOSPQET-UHFFFAOYSA-N ethyl 3-(4-hydroxyphenyl)-2-methyl-2-(2-methylphenoxy)propanoate Chemical compound C=1C=CC=C(C)C=1OC(C)(C(=O)OCC)CC1=CC=C(O)C=C1 ZVDYEIHGOSPQET-UHFFFAOYSA-N 0.000 description 1
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