NO330171B1 - Kirale oksazol-arylpropionsyrederivater, fremgangsmate for fremstilling av slike, farmasoytisk preparat inneholdende slike, slike forbindelser for anvendelse som terapeutisk aktive substanser samt slike forbindelser for behandling og/eller forbygging av sykdom - Google Patents

Info

Publication number

NO330171B1

NO330171B1 NO20051011A NO20051011A NO330171B1 NO 330171 B1 NO330171 B1 NO 330171B1 NO 20051011 A NO20051011 A NO 20051011A NO 20051011 A NO20051011 A NO 20051011A NO 330171 B1 NO330171 B1 NO 330171B1

Authority

NO

Norway

Prior art keywords

phenyl

methyl

ethoxy

propionic acid

oxazol

Prior art date

2002-10-07

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 153
• 238000011282 treatment Methods 0.000 title claims abstract description 45
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• 238000000034 method Methods 0.000 title claims description 210
• 238000002360 preparation method Methods 0.000 title claims description 18
• 239000013543 active substance Substances 0.000 title claims description 5
• 239000002253 acid Substances 0.000 title description 19
• 239000008194 pharmaceutical composition Substances 0.000 title 1
• 150000003839 salts Chemical class 0.000 claims abstract description 49
• 150000002148 esters Chemical class 0.000 claims abstract description 36
• 102000000536 PPAR gamma Human genes 0.000 claims abstract description 16
• 108010016731 PPAR gamma Proteins 0.000 claims abstract description 15
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 14
• 102000023984 PPAR alpha Human genes 0.000 claims abstract description 13
• 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 claims abstract description 13
• 239000000556 agonist Substances 0.000 claims abstract description 7
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 69
• 239000001257 hydrogen Substances 0.000 claims description 37
• 229910052739 hydrogen Inorganic materials 0.000 claims description 37
• -1 4-isopropoxy-phenyl Chemical group 0.000 claims description 34
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
• 125000000217 alkyl group Chemical group 0.000 claims description 26
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
• 229910052736 halogen Inorganic materials 0.000 claims description 13
• 201000010099 disease Diseases 0.000 claims description 12
• 150000002367 halogens Chemical class 0.000 claims description 12
• 125000006239 protecting group Chemical group 0.000 claims description 12
• 125000003545 alkoxy group Chemical group 0.000 claims description 11
• 125000004432 carbon atom Chemical group C* 0.000 claims description 10
• 239000003814 drug Substances 0.000 claims description 10
• FUUHTMVXHFPIBV-NRFANRHFSA-N (2s)-2-ethoxy-3-[4-[[2-(2-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]methoxy]-2-methylphenyl]propanoic acid Chemical compound C1=C(C)C(C[C@H](OCC)C(O)=O)=CC=C1OCC1=C(C)OC(C=2C(=CC=CC=2)F)=N1 FUUHTMVXHFPIBV-NRFANRHFSA-N 0.000 claims description 7
• 239000011737 fluorine Substances 0.000 claims description 7
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• 150000002431 hydrogen Chemical class 0.000 claims description 7
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 6
• 206010012601 diabetes mellitus Diseases 0.000 claims description 6
• 125000001424 substituent group Chemical group 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• YYGRAHKNGNSNKN-QHCPKHFHSA-N (2s)-2-ethoxy-3-[2-ethyl-4-[[2-(4-fluoro-3-methylphenyl)-5-methyl-1,3-oxazol-4-yl]methoxy]phenyl]propanoic acid Chemical compound C1=C(CC)C(C[C@H](OCC)C(O)=O)=CC=C1OCC1=C(C)OC(C=2C=C(C)C(F)=CC=2)=N1 YYGRAHKNGNSNKN-QHCPKHFHSA-N 0.000 claims description 5
• RQVZIUMDNYUGBX-FQEVSTJZSA-N (2s)-2-ethoxy-3-[2-fluoro-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]propanoic acid Chemical compound C1=C(F)C(C[C@H](OCC)C(O)=O)=CC=C1OCC1=C(C)OC(C=2C=CC=CC=2)=N1 RQVZIUMDNYUGBX-FQEVSTJZSA-N 0.000 claims description 5
• LRPJSHRTQQCJNQ-DEOSSOPVSA-N (2s)-2-ethoxy-3-[2-methoxy-4-[[5-methyl-2-(4-propan-2-ylphenyl)-1,3-oxazol-4-yl]methoxy]phenyl]propanoic acid Chemical compound C1=C(OC)C(C[C@H](OCC)C(O)=O)=CC=C1OCC1=C(C)OC(C=2C=CC(=CC=2)C(C)C)=N1 LRPJSHRTQQCJNQ-DEOSSOPVSA-N 0.000 claims description 5
• VRKSVSMXWDYEDJ-NRFANRHFSA-N (2s)-2-ethoxy-3-[2-methyl-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]propanoic acid Chemical compound C1=C(C)C(C[C@H](OCC)C(O)=O)=CC=C1OCC1=C(C)OC(C=2C=CC=CC=2)=N1 VRKSVSMXWDYEDJ-NRFANRHFSA-N 0.000 claims description 5
• YNUGWKSUQZIINS-DEOSSOPVSA-N (2s)-2-ethoxy-3-[2-methyl-4-[[5-methyl-2-(4-propan-2-yloxyphenyl)-1,3-oxazol-4-yl]methoxy]phenyl]propanoic acid Chemical compound C1=C(C)C(C[C@H](OCC)C(O)=O)=CC=C1OCC1=C(C)OC(C=2C=CC(OC(C)C)=CC=2)=N1 YNUGWKSUQZIINS-DEOSSOPVSA-N 0.000 claims description 5
• KQCDKDDDEAUKIZ-FQEVSTJZSA-N (2s)-2-ethoxy-3-[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]-2-(trifluoromethyl)phenyl]propanoic acid Chemical compound C1=C(C(F)(F)F)C(C[C@H](OCC)C(O)=O)=CC=C1OCC1=C(C)OC(C=2C=CC=CC=2)=N1 KQCDKDDDEAUKIZ-FQEVSTJZSA-N 0.000 claims description 5
• CWMCHIQKNCEDFP-QFIPXVFZSA-N (2s)-2-ethoxy-3-[4-[[2-(4-fluoro-3-methylphenyl)-5-methyl-1,3-oxazol-4-yl]methoxy]-2-methylphenyl]propanoic acid Chemical compound C1=C(C)C(C[C@H](OCC)C(O)=O)=CC=C1OCC1=C(C)OC(C=2C=C(C)C(F)=CC=2)=N1 CWMCHIQKNCEDFP-QFIPXVFZSA-N 0.000 claims description 5
• BYQJTFRDTUYQOC-QFIPXVFZSA-N (2s)-3-[2,6-dimethyl-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=C(C)C(C[C@H](OCC)C(O)=O)=C(C)C=C1OCC1=C(C)OC(C=2C=CC=CC=2)=N1 BYQJTFRDTUYQOC-QFIPXVFZSA-N 0.000 claims description 5
• ZKPUTZIBAWOQDX-VWLOTQADSA-N (2s)-3-[2,6-dimethyl-4-[[5-methyl-2-(4-propan-2-ylphenyl)-1,3-oxazol-4-yl]methoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=C(C)C(C[C@H](OCC)C(O)=O)=C(C)C=C1OCC1=C(C)OC(C=2C=CC(=CC=2)C(C)C)=N1 ZKPUTZIBAWOQDX-VWLOTQADSA-N 0.000 claims description 5
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 5
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 5
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
• DTWMPESKZJOAMA-NRFANRHFSA-N (2s)-2-ethoxy-3-[4-[[2-(3-methoxyphenyl)-1,3-oxazol-4-yl]methoxy]-2-methylphenyl]propanoic acid Chemical compound C1=C(C)C(C[C@H](OCC)C(O)=O)=CC=C1OCC1=COC(C=2C=C(OC)C=CC=2)=N1 DTWMPESKZJOAMA-NRFANRHFSA-N 0.000 claims description 4
• APZWKRKCKQRLAW-VWLOTQADSA-N (2s)-3-[4-[[2-(4-tert-butylphenyl)-5-methyl-1,3-oxazol-4-yl]methoxy]-2-ethoxyphenyl]-2-ethoxypropanoic acid Chemical compound C1=C(OCC)C(C[C@H](OCC)C(O)=O)=CC=C1OCC1=C(C)OC(C=2C=CC(=CC=2)C(C)(C)C)=N1 APZWKRKCKQRLAW-VWLOTQADSA-N 0.000 claims description 4
• RDFAZCQKJPQUQU-SANMLTNESA-N (2s)-3-[4-[[2-(4-tert-butylphenyl)-5-methyl-1,3-oxazol-4-yl]methoxy]-2-propan-2-yloxyphenyl]-2-ethoxypropanoic acid Chemical compound C1=C(OC(C)C)C(C[C@H](OCC)C(O)=O)=CC=C1OCC1=C(C)OC(C=2C=CC(=CC=2)C(C)(C)C)=N1 RDFAZCQKJPQUQU-SANMLTNESA-N 0.000 claims description 4
• 239000000460 chlorine Substances 0.000 claims description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
• 150000002632 lipids Chemical class 0.000 claims description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
• 208000032928 Dyslipidaemia Diseases 0.000 claims description 3
• 206010048554 Endothelial dysfunction Diseases 0.000 claims description 3
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• 229910052801 chlorine Inorganic materials 0.000 claims description 3
• 230000008694 endothelial dysfunction Effects 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
• 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
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• XYWQYWCMEQSIHR-IWIPYMOSSA-N ethyl (z)-2-ethoxy-3-[2-methyl-4-[[5-methyl-2-(2-methylphenyl)-1,3-oxazol-4-yl]methoxy]phenyl]prop-2-enoate Chemical compound C1=C(C)C(/C=C(\OCC)C(=O)OCC)=CC=C1OCC1=C(C)OC(C=2C(=CC=CC=2)C)=N1 XYWQYWCMEQSIHR-IWIPYMOSSA-N 0.000 description 2
• VTVSKONUESVWMN-UCQKPKSFSA-N ethyl (z)-2-ethoxy-3-[4-[[2-(2-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]methoxy]-2-methylphenyl]prop-2-enoate Chemical compound C1=C(C)C(/C=C(\OCC)C(=O)OCC)=CC=C1OCC1=C(C)OC(C=2C(=CC=CC=2)F)=N1 VTVSKONUESVWMN-UCQKPKSFSA-N 0.000 description 2
• CKSRFHWWBKRUKA-UHFFFAOYSA-N ethyl 2-ethoxyacetate Chemical compound CCOCC(=O)OCC CKSRFHWWBKRUKA-UHFFFAOYSA-N 0.000 description 2
• 238000002474 experimental method Methods 0.000 description 2
• 239000013613 expression plasmid Substances 0.000 description 2
• 239000003925 fat Substances 0.000 description 2
• 238000001914 filtration Methods 0.000 description 2
• 238000003818 flash chromatography Methods 0.000 description 2
• 125000001153 fluoro group Chemical group F* 0.000 description 2
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
• 125000002541 furyl group Chemical group 0.000 description 2
• 230000014509 gene expression Effects 0.000 description 2
• 125000005456 glyceride group Chemical group 0.000 description 2
• VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
• GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
• 230000001771 impaired effect Effects 0.000 description 2
• 239000004615 ingredient Substances 0.000 description 2
• HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
• AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 2
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
• GTBBGSMCSYZDPA-FQEVSTJZSA-N methyl (2s)-2-ethoxy-3-(2-ethyl-4-phenylmethoxyphenyl)propanoate Chemical compound C1=C(CC)C(C[C@H](OCC)C(=O)OC)=CC=C1OCC1=CC=CC=C1 GTBBGSMCSYZDPA-FQEVSTJZSA-N 0.000 description 2
• OTNSQUGJEAYJHI-SFHVURJKSA-N methyl (2s)-2-ethoxy-3-(2-fluoro-4-phenylmethoxyphenyl)propanoate Chemical compound C1=C(F)C(C[C@H](OCC)C(=O)OC)=CC=C1OCC1=CC=CC=C1 OTNSQUGJEAYJHI-SFHVURJKSA-N 0.000 description 2
• OUMWQDHMTMPXRX-QHCPKHFHSA-N methyl (2s)-2-ethoxy-3-[2-ethyl-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]propanoate Chemical compound C1=C(CC)C(C[C@H](OCC)C(=O)OC)=CC=C1OCC1=C(C)OC(C=2C=CC=CC=2)=N1 OUMWQDHMTMPXRX-QHCPKHFHSA-N 0.000 description 2
• NMKPGURKSFRYKM-QHCPKHFHSA-N methyl (2s)-2-ethoxy-3-[2-ethyl-4-[[2-(2-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]methoxy]phenyl]propanoate Chemical compound C1=C(CC)C(C[C@H](OCC)C(=O)OC)=CC=C1OCC1=C(C)OC(C=2C(=CC=CC=2)F)=N1 NMKPGURKSFRYKM-QHCPKHFHSA-N 0.000 description 2
• SETZDDGCADZRGC-DEOSSOPVSA-N methyl (2s)-2-ethoxy-3-[2-ethyl-4-[[2-(4-fluoro-3-methylphenyl)-5-methyl-1,3-oxazol-4-yl]methoxy]phenyl]propanoate Chemical compound C1=C(CC)C(C[C@H](OCC)C(=O)OC)=CC=C1OCC1=C(C)OC(C=2C=C(C)C(F)=CC=2)=N1 SETZDDGCADZRGC-DEOSSOPVSA-N 0.000 description 2
• JREAFSUVOYZNRH-DEOSSOPVSA-N methyl (2s)-2-ethoxy-3-[2-ethyl-4-[[5-methyl-2-(2-methylphenyl)-1,3-oxazol-4-yl]methoxy]phenyl]propanoate Chemical compound C1=C(CC)C(C[C@H](OCC)C(=O)OC)=CC=C1OCC1=C(C)OC(C=2C(=CC=CC=2)C)=N1 JREAFSUVOYZNRH-DEOSSOPVSA-N 0.000 description 2
• NBZPKILWWSTLRE-SANMLTNESA-N methyl (2s)-2-ethoxy-3-[2-ethyl-4-[[5-methyl-2-(4-propan-2-yloxyphenyl)-1,3-oxazol-4-yl]methoxy]phenyl]propanoate Chemical compound C1=C(CC)C(C[C@H](OCC)C(=O)OC)=CC=C1OCC1=C(C)OC(C=2C=CC(OC(C)C)=CC=2)=N1 NBZPKILWWSTLRE-SANMLTNESA-N 0.000 description 2
• CAKLAEBWCCTFRD-NRFANRHFSA-N methyl (2s)-2-ethoxy-3-[2-fluoro-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]propanoate Chemical compound C1=C(F)C(C[C@H](OCC)C(=O)OC)=CC=C1OCC1=C(C)OC(C=2C=CC=CC=2)=N1 CAKLAEBWCCTFRD-NRFANRHFSA-N 0.000 description 2
• YRQFQHINICOCFK-NRFANRHFSA-N methyl (2s)-2-ethoxy-3-[2-fluoro-4-[[2-(2-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]methoxy]phenyl]propanoate Chemical compound C1=C(F)C(C[C@H](OCC)C(=O)OC)=CC=C1OCC1=C(C)OC(C=2C(=CC=CC=2)F)=N1 YRQFQHINICOCFK-NRFANRHFSA-N 0.000 description 2
• HJKNISVVONZNFB-QFIPXVFZSA-N methyl (2s)-2-ethoxy-3-[2-fluoro-4-[[5-methyl-2-(2-methylphenyl)-1,3-oxazol-4-yl]methoxy]phenyl]propanoate Chemical compound C1=C(F)C(C[C@H](OCC)C(=O)OC)=CC=C1OCC1=C(C)OC(C=2C(=CC=CC=2)C)=N1 HJKNISVVONZNFB-QFIPXVFZSA-N 0.000 description 2
• ABYUHWFKQUZRRP-QFIPXVFZSA-N methyl (2s)-2-ethoxy-3-[2-methoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]propanoate Chemical compound C1=C(OC)C(C[C@H](OCC)C(=O)OC)=CC=C1OCC1=C(C)OC(C=2C=CC=CC=2)=N1 ABYUHWFKQUZRRP-QFIPXVFZSA-N 0.000 description 2
• WVQYGNPHTBBLOV-VWLOTQADSA-N methyl (2s)-2-ethoxy-3-[2-methoxy-4-[[5-methyl-2-(4-propan-2-yloxyphenyl)-1,3-oxazol-4-yl]methoxy]phenyl]propanoate Chemical compound C1=C(OC)C(C[C@H](OCC)C(=O)OC)=CC=C1OCC1=C(C)OC(C=2C=CC(OC(C)C)=CC=2)=N1 WVQYGNPHTBBLOV-VWLOTQADSA-N 0.000 description 2
• AUMHYCAOOYXRFS-VWLOTQADSA-N methyl (2s)-2-ethoxy-3-[2-methoxy-4-[[5-methyl-2-(4-propan-2-ylphenyl)-1,3-oxazol-4-yl]methoxy]phenyl]propanoate Chemical compound C1=C(OC)C(C[C@H](OCC)C(=O)OC)=CC=C1OCC1=C(C)OC(C=2C=CC(=CC=2)C(C)C)=N1 AUMHYCAOOYXRFS-VWLOTQADSA-N 0.000 description 2
• QZQDKZVCQLLVPF-NRFANRHFSA-N methyl (2s)-2-ethoxy-3-[2-methyl-4-[(2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]propanoate Chemical compound C1=C(C)C(C[C@H](OCC)C(=O)OC)=CC=C1OCC1=COC(C=2C=CC=CC=2)=N1 QZQDKZVCQLLVPF-NRFANRHFSA-N 0.000 description 2
• GEKIQLPAKNTPKH-QFIPXVFZSA-N methyl (2s)-2-ethoxy-3-[2-methyl-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]propanoate Chemical compound C1=C(C)C(C[C@H](OCC)C(=O)OC)=CC=C1OCC1=C(C)OC(C=2C=CC=CC=2)=N1 GEKIQLPAKNTPKH-QFIPXVFZSA-N 0.000 description 2
• QCPPDMGDUQQRJU-VWLOTQADSA-N methyl (2s)-2-ethoxy-3-[2-methyl-4-[[5-methyl-2-(4-propan-2-yloxyphenyl)-1,3-oxazol-4-yl]methoxy]phenyl]propanoate Chemical compound C1=C(C)C(C[C@H](OCC)C(=O)OC)=CC=C1OCC1=C(C)OC(C=2C=CC(OC(C)C)=CC=2)=N1 QCPPDMGDUQQRJU-VWLOTQADSA-N 0.000 description 2
• ZMCJTFKZZFYHOE-NRFANRHFSA-N methyl (2s)-2-ethoxy-3-[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]-2-(trifluoromethyl)phenyl]propanoate Chemical compound C1=C(C(F)(F)F)C(C[C@H](OCC)C(=O)OC)=CC=C1OCC1=C(C)OC(C=2C=CC=CC=2)=N1 ZMCJTFKZZFYHOE-NRFANRHFSA-N 0.000 description 2
• QGGUKNFUIPDNJX-NRFANRHFSA-N methyl (2s)-2-ethoxy-3-[4-[[2-(2-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]methoxy]-2-(trifluoromethyl)phenyl]propanoate Chemical compound C1=C(C(F)(F)F)C(C[C@H](OCC)C(=O)OC)=CC=C1OCC1=C(C)OC(C=2C(=CC=CC=2)F)=N1 QGGUKNFUIPDNJX-NRFANRHFSA-N 0.000 description 2
• ASMMBPCWWTWBQL-QFIPXVFZSA-N methyl (2s)-2-ethoxy-3-[4-[[2-(2-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]methoxy]-2-methylphenyl]propanoate Chemical compound C1=C(C)C(C[C@H](OCC)C(=O)OC)=CC=C1OCC1=C(C)OC(C=2C(=CC=CC=2)F)=N1 ASMMBPCWWTWBQL-QFIPXVFZSA-N 0.000 description 2
• CPPZNXHLSHWEMB-QHCPKHFHSA-N methyl (2s)-2-ethoxy-3-[4-[[2-(4-fluoro-3-methylphenyl)-5-methyl-1,3-oxazol-4-yl]methoxy]-2-methoxyphenyl]propanoate Chemical compound C1=C(OC)C(C[C@H](OCC)C(=O)OC)=CC=C1OCC1=C(C)OC(C=2C=C(C)C(F)=CC=2)=N1 CPPZNXHLSHWEMB-QHCPKHFHSA-N 0.000 description 2
• UUARENYMZLGMIU-QHCPKHFHSA-N methyl (2s)-2-ethoxy-3-[4-[[2-(4-fluoro-3-methylphenyl)-5-methyl-1,3-oxazol-4-yl]methoxy]-2-methylphenyl]propanoate Chemical compound C1=C(C)C(C[C@H](OCC)C(=O)OC)=CC=C1OCC1=C(C)OC(C=2C=C(C)C(F)=CC=2)=N1 UUARENYMZLGMIU-QHCPKHFHSA-N 0.000 description 2
• UFWVFXMXXKAUTP-SFHVURJKSA-N methyl (2s)-2-ethoxy-3-[4-phenylmethoxy-2-(trifluoromethyl)phenyl]propanoate Chemical compound C1=C(C(F)(F)F)C(C[C@H](OCC)C(=O)OC)=CC=C1OCC1=CC=CC=C1 UFWVFXMXXKAUTP-SFHVURJKSA-N 0.000 description 2
• VUBMGFARWRVWEQ-FQEVSTJZSA-N methyl (2s)-3-(2,6-dimethyl-4-phenylmethoxyphenyl)-2-ethoxypropanoate Chemical compound C1=C(C)C(C[C@H](OCC)C(=O)OC)=C(C)C=C1OCC1=CC=CC=C1 VUBMGFARWRVWEQ-FQEVSTJZSA-N 0.000 description 2
• QSPTZAARDRZJOB-QHCPKHFHSA-N methyl (2s)-3-[2,6-dimethyl-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=C(C)C(C[C@H](OCC)C(=O)OC)=C(C)C=C1OCC1=C(C)OC(C=2C=CC=CC=2)=N1 QSPTZAARDRZJOB-QHCPKHFHSA-N 0.000 description 2
• NEXDVXGHQDKOBT-SANMLTNESA-N methyl (2s)-3-[2,6-dimethyl-4-[[5-methyl-2-(4-propan-2-yloxyphenyl)-1,3-oxazol-4-yl]methoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=C(C)C(C[C@H](OCC)C(=O)OC)=C(C)C=C1OCC1=C(C)OC(C=2C=CC(OC(C)C)=CC=2)=N1 NEXDVXGHQDKOBT-SANMLTNESA-N 0.000 description 2
• WUEDLBADBZVYDH-SANMLTNESA-N methyl (2s)-3-[2,6-dimethyl-4-[[5-methyl-2-(4-propan-2-ylphenyl)-1,3-oxazol-4-yl]methoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=C(C)C(C[C@H](OCC)C(=O)OC)=C(C)C=C1OCC1=C(C)OC(C=2C=CC(=CC=2)C(C)C)=N1 WUEDLBADBZVYDH-SANMLTNESA-N 0.000 description 2
• NPZBEUMUMDKCHM-NRFANRHFSA-N methyl (2s)-3-[2-chloro-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=C(Cl)C(C[C@H](OCC)C(=O)OC)=CC=C1OCC1=C(C)OC(C=2C=CC=CC=2)=N1 NPZBEUMUMDKCHM-NRFANRHFSA-N 0.000 description 2
• UEFMZASQBVAUKO-NRFANRHFSA-N methyl (2s)-3-[2-chloro-4-[[2-(2-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]methoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=C(Cl)C(C[C@H](OCC)C(=O)OC)=CC=C1OCC1=C(C)OC(C=2C(=CC=CC=2)F)=N1 UEFMZASQBVAUKO-NRFANRHFSA-N 0.000 description 2
• VDYHOFRRFFOTJP-QFIPXVFZSA-N methyl (2s)-3-[2-chloro-4-[[2-(2-methoxyphenyl)-5-methyl-1,3-oxazol-4-yl]methoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=C(Cl)C(C[C@H](OCC)C(=O)OC)=CC=C1OCC1=C(C)OC(C=2C(=CC=CC=2)OC)=N1 VDYHOFRRFFOTJP-QFIPXVFZSA-N 0.000 description 2
• GZPMVXBEMOVYDV-QFIPXVFZSA-N methyl (2s)-3-[2-chloro-4-[[2-(4-fluoro-3-methylphenyl)-5-methyl-1,3-oxazol-4-yl]methoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=C(Cl)C(C[C@H](OCC)C(=O)OC)=CC=C1OCC1=C(C)OC(C=2C=C(C)C(F)=CC=2)=N1 GZPMVXBEMOVYDV-QFIPXVFZSA-N 0.000 description 2
• NNYUOWBAZPRWPU-QFIPXVFZSA-N methyl (2s)-3-[2-chloro-4-[[5-methyl-2-(2-methylphenyl)-1,3-oxazol-4-yl]methoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=C(Cl)C(C[C@H](OCC)C(=O)OC)=CC=C1OCC1=C(C)OC(C=2C(=CC=CC=2)C)=N1 NNYUOWBAZPRWPU-QFIPXVFZSA-N 0.000 description 2
• QDYLDGAXZAUHGL-DEOSSOPVSA-N methyl (2s)-3-[2-chloro-4-[[5-methyl-2-(4-propan-2-yloxyphenyl)-1,3-oxazol-4-yl]methoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=C(Cl)C(C[C@H](OCC)C(=O)OC)=CC=C1OCC1=C(C)OC(C=2C=CC(OC(C)C)=CC=2)=N1 QDYLDGAXZAUHGL-DEOSSOPVSA-N 0.000 description 2
• NPDJTYQABHRXJU-DEOSSOPVSA-N methyl (2s)-3-[4-[[2-(3,5-dimethoxyphenyl)-5-methyl-1,3-oxazol-4-yl]methoxy]-2-methylphenyl]-2-ethoxypropanoate Chemical compound C1=C(C)C(C[C@H](OCC)C(=O)OC)=CC=C1OCC1=C(C)OC(C=2C=C(OC)C=C(OC)C=2)=N1 NPDJTYQABHRXJU-DEOSSOPVSA-N 0.000 description 2
• RENIRDDUQBYEPY-QHCPKHFHSA-N methyl (2s)-3-[4-[[2-(3-chlorophenyl)-5-methyl-1,3-oxazol-4-yl]methoxy]-2,6-dimethylphenyl]-2-ethoxypropanoate Chemical compound C1=C(C)C(C[C@H](OCC)C(=O)OC)=C(C)C=C1OCC1=C(C)OC(C=2C=C(Cl)C=CC=2)=N1 RENIRDDUQBYEPY-QHCPKHFHSA-N 0.000 description 2
• CUIIFBKVFVXOLS-QFIPXVFZSA-N methyl (2s)-3-[4-[[2-(3-chlorophenyl)-5-methyl-1,3-oxazol-4-yl]methoxy]-2-methoxyphenyl]-2-ethoxypropanoate Chemical compound C1=C(OC)C(C[C@H](OCC)C(=O)OC)=CC=C1OCC1=C(C)OC(C=2C=C(Cl)C=CC=2)=N1 CUIIFBKVFVXOLS-QFIPXVFZSA-N 0.000 description 2
• FMFXYYXUSAJMQH-UXHICEINSA-N methyl (2s,3r)-2-ethoxy-3-(2-ethyl-4-phenylmethoxyphenyl)-3-hydroxypropanoate Chemical compound C1=C(CC)C([C@@H](O)[C@H](OCC)C(=O)OC)=CC=C1OCC1=CC=CC=C1 FMFXYYXUSAJMQH-UXHICEINSA-N 0.000 description 2
• PJQUFHBXHMZCDH-MSOLQXFVSA-N methyl (2s,3r)-2-ethoxy-3-(2-fluoro-4-phenylmethoxyphenyl)-3-hydroxypropanoate Chemical compound C1=C(F)C([C@@H](O)[C@H](OCC)C(=O)OC)=CC=C1OCC1=CC=CC=C1 PJQUFHBXHMZCDH-MSOLQXFVSA-N 0.000 description 2
• YDIVROVFFHTBIJ-MOPGFXCFSA-N methyl (2s,3r)-2-ethoxy-3-hydroxy-3-(2-methoxy-4-phenylmethoxyphenyl)propanoate Chemical compound C1=C(OC)C([C@@H](O)[C@H](OCC)C(=O)OC)=CC=C1OCC1=CC=CC=C1 YDIVROVFFHTBIJ-MOPGFXCFSA-N 0.000 description 2
• OANPODAAWMFYGH-MSOLQXFVSA-N methyl (2s,3r)-2-ethoxy-3-hydroxy-3-[4-phenylmethoxy-2-(trifluoromethyl)phenyl]propanoate Chemical compound C1=C(C(F)(F)F)C([C@@H](O)[C@H](OCC)C(=O)OC)=CC=C1OCC1=CC=CC=C1 OANPODAAWMFYGH-MSOLQXFVSA-N 0.000 description 2
• JFFKMVOMSULECI-UXHICEINSA-N methyl (2s,3r)-3-(2,6-dimethyl-4-phenylmethoxyphenyl)-2-ethoxy-3-hydroxypropanoate Chemical compound C1=C(C)C([C@@H](O)[C@H](OCC)C(=O)OC)=C(C)C=C1OCC1=CC=CC=C1 JFFKMVOMSULECI-UXHICEINSA-N 0.000 description 2
• WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 2
• 150000002825 nitriles Chemical class 0.000 description 2
• 229910052757 nitrogen Inorganic materials 0.000 description 2
• 231100000252 nontoxic Toxicity 0.000 description 2
• 230000003000 nontoxic effect Effects 0.000 description 2
• BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 2
• GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 2
• 239000001301 oxygen Substances 0.000 description 2
• 229910052760 oxygen Inorganic materials 0.000 description 2
• 210000000496 pancreas Anatomy 0.000 description 2
• 239000000546 pharmaceutical excipient Substances 0.000 description 2
• ICZHJFWIOPYQCA-UHFFFAOYSA-N pirkle's alcohol Chemical compound C1=CC=C2C(C(O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 ICZHJFWIOPYQCA-UHFFFAOYSA-N 0.000 description 2
• 239000013600 plasmid vector Substances 0.000 description 2
• 239000002798 polar solvent Substances 0.000 description 2
• 230000002265 prevention Effects 0.000 description 2
• 102000004169 proteins and genes Human genes 0.000 description 2
• 108090000623 proteins and genes Proteins 0.000 description 2
• 239000002287 radioligand Substances 0.000 description 2
• 230000009257 reactivity Effects 0.000 description 2
• 229960004586 rosiglitazone Drugs 0.000 description 2
• 238000002821 scintillation proximity assay Methods 0.000 description 2
• 230000007017 scission Effects 0.000 description 2
• 230000008313 sensitization Effects 0.000 description 2
• 239000002002 slurry Substances 0.000 description 2
• 238000010561 standard procedure Methods 0.000 description 2
• 239000007858 starting material Substances 0.000 description 2
• 229910052717 sulfur Inorganic materials 0.000 description 2
• 239000011593 sulfur Substances 0.000 description 2
• 239000000829 suppository Substances 0.000 description 2
• 208000011580 syndromic disease Diseases 0.000 description 2
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
• 230000001225 therapeutic effect Effects 0.000 description 2
• 125000001544 thienyl group Chemical group 0.000 description 2
• XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
• 238000001890 transfection Methods 0.000 description 2
• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
• 235000015112 vegetable and seed oil Nutrition 0.000 description 2
• 239000008158 vegetable oil Substances 0.000 description 2
• 238000005406 washing Methods 0.000 description 2
• FCRDIJHLAPKHSP-UHFFFAOYSA-M (1,2-dimethoxy-2-oxoethyl)-triphenylphosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C(C(=O)OC)OC)C1=CC=CC=C1 FCRDIJHLAPKHSP-UHFFFAOYSA-M 0.000 description 1
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