HRP20040164A2 - Oral antidiabetic agents - Google Patents
Oral antidiabetic agents Download PDFInfo
- Publication number
- HRP20040164A2 HRP20040164A2 HR20040164A HRP20040164A HRP20040164A2 HR P20040164 A2 HRP20040164 A2 HR P20040164A2 HR 20040164 A HR20040164 A HR 20040164A HR P20040164 A HRP20040164 A HR P20040164A HR P20040164 A2 HRP20040164 A2 HR P20040164A2
- Authority
- HR
- Croatia
- Prior art keywords
- phenyl
- methyl
- oxazol
- propionic acid
- ethoxy
- Prior art date
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- 239000003538 oral antidiabetic agent Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 278
- -1 (S)-3,3,3-trifluoromethyl-2-{4-[2-(methyl-pyridin-2-yl-amino)-ethoxy]-benzyl}-2-pyrrol-1-yl-propionic acid Chemical compound 0.000 claims description 203
- 125000001072 heteroaryl group Chemical group 0.000 claims description 183
- 150000004702 methyl esters Chemical class 0.000 claims description 166
- 238000000034 method Methods 0.000 claims description 162
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 118
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 64
- 125000003118 aryl group Chemical group 0.000 claims description 51
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 46
- 150000002148 esters Chemical group 0.000 claims description 41
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 38
- 125000003107 substituted aryl group Chemical group 0.000 claims description 38
- 125000005843 halogen group Chemical group 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 35
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 35
- 241000124008 Mammalia Species 0.000 claims description 34
- 238000002360 preparation method Methods 0.000 claims description 31
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 30
- 125000004429 atom Chemical group 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 230000007062 hydrolysis Effects 0.000 claims description 29
- 238000006460 hydrolysis reaction Methods 0.000 claims description 29
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 26
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 22
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- PQZYHRIRPYDIKV-LJAQVGFWSA-N (2s)-2-(2-benzoylpyrrol-1-yl)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound N1([C@H](C(O)=O)CC2=CC=C(C=C2)OCCC=2N=C(OC=2C)C=2C=CC=CC=2)C=CC=C1C(=O)C1=CC=CC=C1 PQZYHRIRPYDIKV-LJAQVGFWSA-N 0.000 claims description 18
- OCWDFPOKWYMLGH-QHCPKHFHSA-N (2s)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-pyrrol-1-ylpropanoic acid Chemical compound N1([C@H](C(O)=O)CC2=CC=C(C=C2)OCCC=2N=C(OC=2C)C=2C=CC=CC=2)C=CC=C1 OCWDFPOKWYMLGH-QHCPKHFHSA-N 0.000 claims description 18
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 18
- ZHXIOHVUENYDOL-LJAQVGFWSA-N (2s)-2-(3-benzoylpyrrol-1-yl)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound C=1N([C@H](C(O)=O)CC2=CC=C(C=C2)OCCC=2N=C(OC=2C)C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 ZHXIOHVUENYDOL-LJAQVGFWSA-N 0.000 claims description 17
- NJCBDXLIRAJPLS-SANMLTNESA-N (2s)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-[3-(2-methylpropanoyl)pyrrol-1-yl]propanoic acid Chemical compound C1=C(C(=O)C(C)C)C=CN1[C@H](C(O)=O)CC(C=C1)=CC=C1OCCC1=C(C)OC(C=2C=CC=CC=2)=N1 NJCBDXLIRAJPLS-SANMLTNESA-N 0.000 claims description 17
- 230000000694 effects Effects 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 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 15
- 239000008103 glucose Substances 0.000 claims description 15
- ZUBRBWGGRARQRI-LJAQVGFWSA-N (2s)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-(3-phenylpyrrol-1-yl)propanoic acid Chemical compound C=1N([C@H](C(O)=O)CC2=CC=C(C=C2)OCCC=2N=C(OC=2C)C=2C=CC=CC=2)C=CC=1C1=CC=CC=C1 ZUBRBWGGRARQRI-LJAQVGFWSA-N 0.000 claims description 13
- UJRNFRMHECOQQV-QHCPKHFHSA-N (2s)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-[2-(2,2,2-trifluoroacetyl)pyrrol-1-yl]propanoic acid Chemical compound N1([C@H](C(O)=O)CC2=CC=C(C=C2)OCCC=2N=C(OC=2C)C=2C=CC=CC=2)C=CC=C1C(=O)C(F)(F)F UJRNFRMHECOQQV-QHCPKHFHSA-N 0.000 claims description 12
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 12
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 12
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims description 11
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims description 11
- 125000005862 (C1-C6)alkanoyl group Chemical group 0.000 claims description 10
- LBIXXUITJJTXPF-UHFFFAOYSA-N 3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-phenylpropanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C(O)=O)C1=CC=CC=C1 LBIXXUITJJTXPF-UHFFFAOYSA-N 0.000 claims description 10
- LVDYSMJSMKIUSK-SANMLTNESA-N methyl (2s)-2-[3-(cyclohexanecarbonyl)pyrrol-1-yl]-3-[4-[(2-fluorophenyl)methoxy]phenyl]propanoate Chemical compound C([C@@H](C(=O)OC)N1C=C(C=C1)C(=O)C1CCCCC1)C(C=C1)=CC=C1OCC1=CC=CC=C1F LVDYSMJSMKIUSK-SANMLTNESA-N 0.000 claims description 10
- XQBDBMQFQDQOCN-DEOSSOPVSA-N methyl (2s)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-pyrrol-1-ylpropanoate Chemical compound C([C@@H](C(=O)OC)N1C=CC=C1)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 XQBDBMQFQDQOCN-DEOSSOPVSA-N 0.000 claims description 10
- KGGDVVRRHQSPJL-VWLOTQADSA-N (2s)-2-(2-acetylpyrrol-1-yl)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound CC(=O)C1=CC=CN1[C@H](C(O)=O)CC(C=C1)=CC=C1OCCC1=C(C)OC(C=2C=CC=CC=2)=N1 KGGDVVRRHQSPJL-VWLOTQADSA-N 0.000 claims description 9
- MNCGKFJYPWUOPJ-LJAQVGFWSA-N (2s)-2-[3-(cyclohexanecarbonyl)pyrrol-1-yl]-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound C=1N([C@H](C(O)=O)CC2=CC=C(C=C2)OCCC=2N=C(OC=2C)C=2C=CC=CC=2)C=CC=1C(=O)C1CCCCC1 MNCGKFJYPWUOPJ-LJAQVGFWSA-N 0.000 claims description 9
- QUYJNEATEFDHGD-UHFFFAOYSA-N 3-[4-[2-(2-phenylbenzimidazol-1-yl)ethoxy]phenyl]-2-pyrrol-1-ylpropanoic acid Chemical compound C1=CC=CN1C(C(=O)O)CC(C=C1)=CC=C1OCCN(C1=CC=CC=C1N=1)C=1C1=CC=CC=C1 QUYJNEATEFDHGD-UHFFFAOYSA-N 0.000 claims description 9
- JAWOTKBIMSEVQH-UHFFFAOYSA-N 3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propanoyl]phenyl]-2-pyrrol-1-ylpropanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCC(=O)C(C=C1)=CC=C1CC(C(O)=O)N1C=CC=C1 JAWOTKBIMSEVQH-UHFFFAOYSA-N 0.000 claims description 9
- AHEFRDNJOUWPAR-NRFANRHFSA-N methyl (2s)-2-pyrrol-1-yl-3-[4-[2-[2-(trifluoromethyl)phenyl]ethoxy]phenyl]propanoate Chemical compound C([C@@H](C(=O)OC)N1C=CC=C1)C(C=C1)=CC=C1OCCC1=CC=CC=C1C(F)(F)F AHEFRDNJOUWPAR-NRFANRHFSA-N 0.000 claims description 9
- TYQHTSFEWNTEJR-SANMLTNESA-N (2s)-2-(3-acetyl-2,5-dimethylpyrrol-1-yl)-3-[4-[2-(4-methyl-2-phenyl-1,3-oxazol-5-yl)ethoxy]phenyl]propanoic acid Chemical compound CC1=C(C(=O)C)C=C(C)N1[C@H](C(O)=O)CC(C=C1)=CC=C1OCCC1=C(C)N=C(C=2C=CC=CC=2)O1 TYQHTSFEWNTEJR-SANMLTNESA-N 0.000 claims description 8
- FXVLTJPOZJQCCD-VWLOTQADSA-N (2s)-2-[2,5-dimethyl-3-(2,2,2-trifluoroacetyl)pyrrol-1-yl]-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound CC1=CC(C(=O)C(F)(F)F)=C(C)N1[C@H](C(O)=O)CC(C=C1)=CC=C1OCCC1=C(C)OC(C=2C=CC=CC=2)=N1 FXVLTJPOZJQCCD-VWLOTQADSA-N 0.000 claims description 8
- UBBHVGYLWGNGBH-UHFFFAOYSA-N 3,3,3-trifluoro-2-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methyl]-2-pyrrol-1-ylpropanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C(O)=O)(C(F)(F)F)N1C=CC=C1 UBBHVGYLWGNGBH-UHFFFAOYSA-N 0.000 claims description 8
- JVGJXYAYHPIKNP-UHFFFAOYSA-N 3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-phenylprop-2-enoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1C=C(C(O)=O)C1=CC=CC=C1 JVGJXYAYHPIKNP-UHFFFAOYSA-N 0.000 claims description 8
- OSSJMBVEKCHVPM-UHFFFAOYSA-N 3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]phenyl]-2-phenylpropanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCCC(C=C1)=CC=C1CC(C(O)=O)C1=CC=CC=C1 OSSJMBVEKCHVPM-UHFFFAOYSA-N 0.000 claims description 8
- 101100134922 Gallus gallus COR5 gene Proteins 0.000 claims description 8
- 210000004369 blood Anatomy 0.000 claims description 8
- 239000008280 blood Substances 0.000 claims description 8
- 125000001589 carboacyl group Chemical group 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- VSCASHDOESJRRJ-SANMLTNESA-N (2s)-3-[4-[2-[1,3-benzoxazol-2-yl(methyl)amino]ethoxy]phenyl]-2-[3-(cyclohexanecarbonyl)pyrrol-1-yl]propanoic acid Chemical compound C=1N([C@H](C(O)=O)CC2=CC=C(C=C2)OCCN(C)C=2OC3=CC=CC=C3N=2)C=CC=1C(=O)C1CCCCC1 VSCASHDOESJRRJ-SANMLTNESA-N 0.000 claims description 7
- YOGDGDDDJHDKLI-UHFFFAOYSA-N 2,2-dimethyl-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-n-methylsulfonylpropanamide Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC1=CC=C(CC(C)(C)C(=O)NS(C)(=O)=O)C=C1 YOGDGDDDJHDKLI-UHFFFAOYSA-N 0.000 claims description 7
- UUVNRTQCORFXQY-UHFFFAOYSA-N 5-methyl-4-[2-[4-[2-(2-methyltetrazol-5-yl)-2-phenylethyl]phenoxy]ethyl]-2-phenyl-1,3-oxazole Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C=1C=CC=CC=1)C=1N=NN(C)N=1 UUVNRTQCORFXQY-UHFFFAOYSA-N 0.000 claims description 7
- 210000001789 adipocyte Anatomy 0.000 claims description 7
- 201000001421 hyperglycemia Diseases 0.000 claims description 7
- SIBSMTONDYSJBO-PMERELPUSA-N (2s)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-(2-methyl-5-phenylpyrrol-1-yl)propanoic acid Chemical compound N1([C@@H](CC=2C=CC(OCCC3=C(OC(=N3)C=3C=CC=CC=3)C)=CC=2)C(O)=O)C(C)=CC=C1C1=CC=CC=C1 SIBSMTONDYSJBO-PMERELPUSA-N 0.000 claims description 6
- VRGLNXQOUDDYNQ-QHCPKHFHSA-N (2s)-3-[4-[2-(5-methyl-2-phenyl-1,3-thiazol-4-yl)ethoxy]phenyl]-2-pyrrol-1-ylpropanoic acid Chemical compound N1([C@H](C(O)=O)CC2=CC=C(C=C2)OCCC=2N=C(SC=2C)C=2C=CC=CC=2)C=CC=C1 VRGLNXQOUDDYNQ-QHCPKHFHSA-N 0.000 claims description 6
- QEHMZPKOFNABFC-SANMLTNESA-N (2s)-3-[4-[2-[1,3-benzoxazol-2-yl(methyl)amino]ethoxy]phenyl]-2-(3-phenylpyrrol-1-yl)propanoic acid Chemical compound C=1N([C@H](C(O)=O)CC2=CC=C(C=C2)OCCN(C)C=2OC3=CC=CC=C3N=2)C=CC=1C1=CC=CC=C1 QEHMZPKOFNABFC-SANMLTNESA-N 0.000 claims description 6
- XUQKEXRPNOKPQU-HKBQPEDESA-N (2s)-3-[4-[[benzyl-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethyl]amino]methyl]phenyl]-2-pyrrol-1-ylpropanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCN(CC=1C=CC(C[C@@H](C(O)=O)N2C=CC=C2)=CC=1)CC1=CC=CC=C1 XUQKEXRPNOKPQU-HKBQPEDESA-N 0.000 claims description 6
- YXCMAAXKGPSTAR-UHFFFAOYSA-N 2-(3-bromopyrrol-1-yl)-2-methyl-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)N1C=CC(Br)=C1 YXCMAAXKGPSTAR-UHFFFAOYSA-N 0.000 claims description 6
- PYXZGFORPUEYGM-UHFFFAOYSA-N 2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)-3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCCC(C=C1)=CC=C1CC(C(O)=O)C(=C(O1)C)N=C1C1=CC=CC=C1 PYXZGFORPUEYGM-UHFFFAOYSA-N 0.000 claims description 6
- XDVYBSONSPJXRD-VWLOTQADSA-N 2-ethyl-5-[(1s)-2-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-1-pyrrol-1-ylethyl]-1,3,4-oxadiazole Chemical compound O1C(CC)=NN=C1[C@@H](N1C=CC=C1)CC(C=C1)=CC=C1OCCC1=C(C)OC(C=2C=CC=CC=2)=N1 XDVYBSONSPJXRD-VWLOTQADSA-N 0.000 claims description 6
- XGEWRQLHGONYJS-UHFFFAOYSA-N 3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-pyridin-3-ylpropanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C(O)=O)C1=CC=CN=C1 XGEWRQLHGONYJS-UHFFFAOYSA-N 0.000 claims description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
- ZSQAVXHIBPNGHG-UHFFFAOYSA-N methyl 2-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methylamino]-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C(=O)OC)NCC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 ZSQAVXHIBPNGHG-UHFFFAOYSA-N 0.000 claims description 6
- BZNSKKDWJQESLV-VWLOTQADSA-N (2s)-2-(2,5-dimethylpyrrol-1-yl)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound CC1=CC=C(C)N1[C@H](C(O)=O)CC(C=C1)=CC=C1OCCC1=C(C)OC(C=2C=CC=CC=2)=N1 BZNSKKDWJQESLV-VWLOTQADSA-N 0.000 claims description 5
- HBEXJSSFQLDYEW-VWLOTQADSA-N (2s)-2-(3-chloro-2,5-dimethylpyrrol-1-yl)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound CC1=CC(Cl)=C(C)N1[C@H](C(O)=O)CC(C=C1)=CC=C1OCCC1=C(C)OC(C=2C=CC=CC=2)=N1 HBEXJSSFQLDYEW-VWLOTQADSA-N 0.000 claims description 5
- ZHJNXKYRCPWMQI-FQEVSTJZSA-N (2s)-2-pyrrol-1-yl-3-[4-[2-[2-(trifluoromethyl)phenyl]ethoxy]phenyl]propanoic acid Chemical compound C([C@@H](C(=O)O)N1C=CC=C1)C(C=C1)=CC=C1OCCC1=CC=CC=C1C(F)(F)F ZHJNXKYRCPWMQI-FQEVSTJZSA-N 0.000 claims description 5
- PPCMBFLHKRFGQJ-UHFFFAOYSA-N 2-(1-methylindol-3-yl)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound N=1C(CCOC=2C=CC(CC(C(O)=O)C=3C4=CC=CC=C4N(C)C=3)=CC=2)=C(C)OC=1C1=CC=CC=C1 PPCMBFLHKRFGQJ-UHFFFAOYSA-N 0.000 claims description 5
- ZLQQPRZPAXDWKJ-UHFFFAOYSA-N 2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C(O)=O)C(=C(O1)C)N=C1C1=CC=CC=C1 ZLQQPRZPAXDWKJ-UHFFFAOYSA-N 0.000 claims description 5
- AKIGVDRXHAKLLX-SANMLTNESA-N 2-[(1s)-2-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-1-pyrrol-1-ylethyl]-5-propyl-1,3,4-oxadiazole Chemical compound O1C(CCC)=NN=C1[C@@H](N1C=CC=C1)CC(C=C1)=CC=C1OCCC1=C(C)OC(C=2C=CC=CC=2)=N1 AKIGVDRXHAKLLX-SANMLTNESA-N 0.000 claims description 5
- VODXFLFSOCGHDO-UHFFFAOYSA-N 3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-thiophen-2-ylpropanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C(O)=O)C1=CC=CS1 VODXFLFSOCGHDO-UHFFFAOYSA-N 0.000 claims description 5
- JACDSBBKKTUZFY-UHFFFAOYSA-N 3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]phenyl]-n-methylsulfonyl-2-pyrrol-1-ylpropanamide Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCCC(C=C1)=CC=C1CC(C(=O)NS(C)(=O)=O)N1C=CC=C1 JACDSBBKKTUZFY-UHFFFAOYSA-N 0.000 claims description 5
- WRDXRBNZWHJVDL-UHFFFAOYSA-N 3-[5-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]indol-1-yl]propanoic acid Chemical compound N=1C(CCOC=2C=C3C=CN(CCC(O)=O)C3=CC=2)=C(C)OC=1C1=CC=CC=C1 WRDXRBNZWHJVDL-UHFFFAOYSA-N 0.000 claims description 5
- BBYKCSILQYJRIP-UHFFFAOYSA-N 3-[6-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]pyridin-3-yl]-2-phenylpropanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(N=C1)=CC=C1CC(C(O)=O)C1=CC=CC=C1 BBYKCSILQYJRIP-UHFFFAOYSA-N 0.000 claims description 5
- 201000001320 Atherosclerosis Diseases 0.000 claims description 5
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 5
- 230000024245 cell differentiation Effects 0.000 claims description 5
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims description 5
- 201000008980 hyperinsulinism Diseases 0.000 claims description 5
- MATLGFQYRJSJTP-MHZLTWQESA-N methyl (2s)-2-methyl-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-pyrrol-1-ylpropanoate Chemical compound C([C@@](C)(C(=O)OC)N1C=CC=C1)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 MATLGFQYRJSJTP-MHZLTWQESA-N 0.000 claims description 5
- DNVJSLRFAMRVQU-UHFFFAOYSA-N methyl 3-[1-[[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]phenyl]methyl]pyrrol-2-yl]propanoate Chemical compound COC(=O)CCC1=CC=CN1CC(C=C1)=CC=C1CCCC1=C(C)OC(C=2C=CC=CC=2)=N1 DNVJSLRFAMRVQU-UHFFFAOYSA-N 0.000 claims description 5
- WOWQWNPNCQWFLR-UHFFFAOYSA-N methyl 3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]phenyl]-2-phenylpropanoate Chemical compound C=1C=CC=CC=1C(C(=O)OC)CC(C=C1)=CC=C1CCCC(=C(O1)C)N=C1C1=CC=CC=C1 WOWQWNPNCQWFLR-UHFFFAOYSA-N 0.000 claims description 5
- LWYUQFVNNCPIGM-DEOSSOPVSA-N (2s)-3-[4-[2-(4-phenylpiperazin-1-yl)ethoxy]phenyl]-2-pyrrol-1-ylpropanoic acid Chemical compound C([C@@H](C(=O)O)N1C=CC=C1)C(C=C1)=CC=C1OCCN(CC1)CCN1C1=CC=CC=C1 LWYUQFVNNCPIGM-DEOSSOPVSA-N 0.000 claims description 4
- SKCIGOUTCJBAPL-PMERELPUSA-N (2s)-3-[4-[[benzoyl-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethyl]amino]methyl]phenyl]-2-pyrrol-1-ylpropanoic acid Chemical compound N1([C@H](C(O)=O)CC2=CC=C(C=C2)CN(CCC=2N=C(OC=2C)C=2C=CC=CC=2)C(=O)C=2C=CC=CC=2)C=CC=C1 SKCIGOUTCJBAPL-PMERELPUSA-N 0.000 claims description 4
- XKPVWQAFWNIURI-UHFFFAOYSA-N 2-[1-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethyl]indol-5-yl]oxy-2-phenylacetic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCN(C1=CC=2)C=CC1=CC=2OC(C(O)=O)C1=CC=CC=C1 XKPVWQAFWNIURI-UHFFFAOYSA-N 0.000 claims description 4
- ADDVMYLGBJGTNM-UHFFFAOYSA-N 2-fluoro-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-n-methylsulfonyl-2-phenylpropanamide Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(F)(C(=O)NS(C)(=O)=O)C1=CC=CC=C1 ADDVMYLGBJGTNM-UHFFFAOYSA-N 0.000 claims description 4
- SGJRZXJGUKOVKK-UHFFFAOYSA-N 2-methyl-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-thiophen-2-ylpropanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)C1=CC=CS1 SGJRZXJGUKOVKK-UHFFFAOYSA-N 0.000 claims description 4
- INUCJURLBTYGAV-UHFFFAOYSA-N 3-[3-ethyl-4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-pyrrol-1-ylpropanoic acid Chemical compound C=1C=C(OCCC2=C(OC(=N2)C=2C=CC=CC=2)C)C(CC)=CC=1CC(C(O)=O)N1C=CC=C1 INUCJURLBTYGAV-UHFFFAOYSA-N 0.000 claims description 4
- ZZEOCBJBHZBZQW-UHFFFAOYSA-N 3-[3-methoxy-4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-pyrrol-1-ylpropanoic acid Chemical compound C=1C=C(OCCC2=C(OC(=N2)C=2C=CC=CC=2)C)C(OC)=CC=1CC(C(O)=O)N1C=CC=C1 ZZEOCBJBHZBZQW-UHFFFAOYSA-N 0.000 claims description 4
- BVOHTKZRVSWGFE-UHFFFAOYSA-N 3-[3-methoxy-4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)prop-1-enyl]phenyl]-2-pyrrol-1-ylpropanoic acid Chemical compound C=1C=C(C=CCC2=C(OC(=N2)C=2C=CC=CC=2)C)C(OC)=CC=1CC(C(O)=O)N1C=CC=C1 BVOHTKZRVSWGFE-UHFFFAOYSA-N 0.000 claims description 4
- STZBJCYNBNMLDB-UHFFFAOYSA-N 3-[3-methoxy-4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]phenyl]-2-pyrrol-1-ylpropanoic acid Chemical compound C=1C=C(CCCC2=C(OC(=N2)C=2C=CC=CC=2)C)C(OC)=CC=1CC(C(O)=O)N1C=CC=C1 STZBJCYNBNMLDB-UHFFFAOYSA-N 0.000 claims description 4
- HQCQFXTVZFEPAA-UHFFFAOYSA-N 3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-3-phenylphenyl]-2-pyrrol-1-ylpropanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C(=C1)C=2C=CC=CC=2)=CC=C1CC(C(O)=O)N1C=CC=C1 HQCQFXTVZFEPAA-UHFFFAOYSA-N 0.000 claims description 4
- YEGWEDCREQUCMX-UHFFFAOYSA-N 3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-3-prop-1-ynylphenyl]-2-pyrrol-1-ylpropanoic acid Chemical compound C=1C=C(OCCC2=C(OC(=N2)C=2C=CC=CC=2)C)C(C#CC)=CC=1CC(C(O)=O)N1C=CC=C1 YEGWEDCREQUCMX-UHFFFAOYSA-N 0.000 claims description 4
- GFUJQCXKDXZMLJ-UHFFFAOYSA-N 3-[4-[2-[2-(trifluoromethyl)phenyl]ethoxy]indol-1-yl]propanoic acid Chemical compound C1=CC=C2N(CCC(=O)O)C=CC2=C1OCCC1=CC=CC=C1C(F)(F)F GFUJQCXKDXZMLJ-UHFFFAOYSA-N 0.000 claims description 4
- PWCJRVHHEVIVSL-UHFFFAOYSA-N 3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)prop-1-ynyl]phenyl]-2-(3-phenylphenyl)propanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CC#CC(C=C1)=CC=C1CC(C(O)=O)C(C=1)=CC=CC=1C1=CC=CC=C1 PWCJRVHHEVIVSL-UHFFFAOYSA-N 0.000 claims description 4
- XKEQYIWVQUGPSH-UHFFFAOYSA-N 3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]phenyl]-2-(triazol-1-yl)propanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCCC(C=C1)=CC=C1CC(C(O)=O)N1C=CN=N1 XKEQYIWVQUGPSH-UHFFFAOYSA-N 0.000 claims description 4
- FBTLXMKHTKDMQC-UHFFFAOYSA-N 3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]phenyl]-2-pyridin-3-ylpropanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCCC(C=C1)=CC=C1CC(C(O)=O)C1=CC=CN=C1 FBTLXMKHTKDMQC-UHFFFAOYSA-N 0.000 claims description 4
- RQLMPQLPTSPYLH-UHFFFAOYSA-N 4-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]phenyl]-2-pyrrol-1-ylbutanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCCC(C=C1)=CC=C1CCC(C(O)=O)N1C=CC=C1 RQLMPQLPTSPYLH-UHFFFAOYSA-N 0.000 claims description 4
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 4
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 4
- 208000008589 Obesity Diseases 0.000 claims description 4
- 208000006575 hypertriglyceridemia Diseases 0.000 claims description 4
- SETPALXCWJNZDY-UHFFFAOYSA-N methyl 2-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methylamino]-2-phenylpropanoate Chemical compound C=1C=CC=CC=1C(C)(C(=O)OC)NCC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 SETPALXCWJNZDY-UHFFFAOYSA-N 0.000 claims description 4
- IJWXLTHSXSLDOL-UHFFFAOYSA-N methyl 2-pyrrol-1-yl-4-[4-(trifluoromethylsulfonyl)phenyl]butanoate Chemical compound C1=CC=CN1C(C(=O)OC)CCC1=CC=C(S(=O)(=O)C(F)(F)F)C=C1 IJWXLTHSXSLDOL-UHFFFAOYSA-N 0.000 claims description 4
- UEHLTCXGEXEQDX-UHFFFAOYSA-N methyl 3-[1-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]piperidin-4-yl]-2-pyrrol-1-ylpropanoate Chemical compound C1=CC=CN1C(C(=O)OC)CC(CC1)CCN1CCCC(=C(O1)C)N=C1C1=CC=CC=C1 UEHLTCXGEXEQDX-UHFFFAOYSA-N 0.000 claims description 4
- VZUXNGLWGYCLIR-UHFFFAOYSA-N methyl 3-[3-ethyl-4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-pyrrol-1-ylpropanoate Chemical compound C=1C=C(OCCC2=C(OC(=N2)C=2C=CC=CC=2)C)C(CC)=CC=1CC(C(=O)OC)N1C=CC=C1 VZUXNGLWGYCLIR-UHFFFAOYSA-N 0.000 claims description 4
- FTJOBRYFSLVOHL-UHFFFAOYSA-N methyl 3-[3-iodo-4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-pyrrol-1-ylpropanoate Chemical compound C1=CC=CN1C(C(=O)OC)CC(C=C1I)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 FTJOBRYFSLVOHL-UHFFFAOYSA-N 0.000 claims description 4
- VYCKIMGGWRJYHF-UHFFFAOYSA-N methyl 3-[3-methoxy-4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-pyrrol-1-ylpropanoate Chemical compound C1=CC=CN1C(C(=O)OC)CC(C=C1OC)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 VYCKIMGGWRJYHF-UHFFFAOYSA-N 0.000 claims description 4
- RHTZRKQHEOXKTH-UHFFFAOYSA-N methyl 3-[3-methoxy-4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]phenyl]-2-pyrrol-1-ylpropanoate Chemical compound C1=CC=CN1C(C(=O)OC)CC(C=C1OC)=CC=C1CCCC(=C(O1)C)N=C1C1=CC=CC=C1 RHTZRKQHEOXKTH-UHFFFAOYSA-N 0.000 claims description 4
- LWNOMJSKJHDWSX-UHFFFAOYSA-N methyl 3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-3-phenylphenyl]-2-pyrrol-1-ylpropanoate Chemical compound C1=CC=CN1C(C(=O)OC)CC(C=C1C=2C=CC=CC=2)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 LWNOMJSKJHDWSX-UHFFFAOYSA-N 0.000 claims description 4
- XTOVFZWWPYZKQZ-UHFFFAOYSA-N methyl 3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-3-prop-1-ynylphenyl]-2-pyrrol-1-ylpropanoate Chemical compound C1=CC=CN1C(C(=O)OC)CC(C=C1C#CC)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 XTOVFZWWPYZKQZ-UHFFFAOYSA-N 0.000 claims description 4
- JLIWNAJXMOPWMH-UHFFFAOYSA-N methyl 3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-phenylpropanoate Chemical compound C=1C=CC=CC=1C(C(=O)OC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 JLIWNAJXMOPWMH-UHFFFAOYSA-N 0.000 claims description 4
- MEISTNYFGXNIBT-UHFFFAOYSA-N methyl 3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-pyridin-3-ylpropanoate Chemical compound C=1C=CN=CC=1C(C(=O)OC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 MEISTNYFGXNIBT-UHFFFAOYSA-N 0.000 claims description 4
- UVVIIXCVYIGBAN-UHFFFAOYSA-N methyl 3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-pyridin-4-ylpropanoate Chemical compound C=1C=NC=CC=1C(C(=O)OC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 UVVIIXCVYIGBAN-UHFFFAOYSA-N 0.000 claims description 4
- OHBAGACJQPEIPT-UHFFFAOYSA-N methyl 3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]phenyl]-2-pyridin-3-ylpropanoate Chemical compound C=1C=CN=CC=1C(C(=O)OC)CC(C=C1)=CC=C1CCCC(=C(O1)C)N=C1C1=CC=CC=C1 OHBAGACJQPEIPT-UHFFFAOYSA-N 0.000 claims description 4
- CCTLXYUWGJRZMN-UHFFFAOYSA-N methyl 3-[6-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]pyridin-3-yl]-2-phenylpropanoate Chemical compound C=1C=CC=CC=1C(C(=O)OC)CC(C=N1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 CCTLXYUWGJRZMN-UHFFFAOYSA-N 0.000 claims description 4
- RZCHTUWMMFWYBX-UHFFFAOYSA-N methyl 4-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]phenyl]-2-pyrrol-1-ylbutanoate Chemical compound C1=CC=CN1C(C(=O)OC)CCC(C=C1)=CC=C1CCCC(=C(O1)C)N=C1C1=CC=CC=C1 RZCHTUWMMFWYBX-UHFFFAOYSA-N 0.000 claims description 4
- ZAXQRWRRNPKBNK-UHFFFAOYSA-N methyl butane-1-sulfonate Chemical compound CCCCS(=O)(=O)OC ZAXQRWRRNPKBNK-UHFFFAOYSA-N 0.000 claims description 4
- 235000020824 obesity Nutrition 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- LBIXXUITJJTXPF-XMMPIXPASA-N (2r)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-phenylpropanoic acid Chemical compound C1([C@H](C(O)=O)CC2=CC=C(C=C2)OCCC=2N=C(OC=2C)C=2C=CC=CC=2)=CC=CC=C1 LBIXXUITJJTXPF-XMMPIXPASA-N 0.000 claims description 3
- SIAWVFNXECNOFD-NRFANRHFSA-N (2s)-2-(2,5-dimethylpyrrol-1-yl)-3-[4-[(2-fluorophenyl)methoxy]phenyl]propanoic acid Chemical compound CC1=CC=C(C)N1[C@H](C(O)=O)CC(C=C1)=CC=C1OCC1=CC=CC=C1F SIAWVFNXECNOFD-NRFANRHFSA-N 0.000 claims description 3
- OJPRZGDPRAOMOZ-SANMLTNESA-N (2s)-2-(2-butanoylpyrrol-1-yl)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound CCCC(=O)C1=CC=CN1[C@H](C(O)=O)CC(C=C1)=CC=C1OCCC1=C(C)OC(C=2C=CC=CC=2)=N1 OJPRZGDPRAOMOZ-SANMLTNESA-N 0.000 claims description 3
- NEUYSXKUUOQMJX-DEOSSOPVSA-N (2s)-3-[4-[2-[(7-chloroquinolin-4-yl)-methylamino]ethoxy]phenyl]-2-pyrrol-1-ylpropanoic acid Chemical compound N1([C@H](C(O)=O)CC2=CC=C(C=C2)OCCN(C)C=2C3=CC=C(Cl)C=C3N=CC=2)C=CC=C1 NEUYSXKUUOQMJX-DEOSSOPVSA-N 0.000 claims description 3
- FEPCXOMAEYJSAM-UHFFFAOYSA-N 2,2-dimethyl-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC1=CC=C(CC(C)(C)C(O)=O)C=C1 FEPCXOMAEYJSAM-UHFFFAOYSA-N 0.000 claims description 3
- BUEFGQKLHLISPZ-UHFFFAOYSA-N 2-(2-bromopyrrol-1-yl)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C(O)=O)N1C=CC=C1Br BUEFGQKLHLISPZ-UHFFFAOYSA-N 0.000 claims description 3
- HDHSCZQBSKWNDL-UHFFFAOYSA-N 2-(2-chloropyrrol-1-yl)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C(O)=O)N1C=CC=C1Cl HDHSCZQBSKWNDL-UHFFFAOYSA-N 0.000 claims description 3
- BLEXBLKEOIMMPG-UHFFFAOYSA-N 2-(4-phenylmethoxyindol-1-yl)propanoic acid Chemical compound C1=CC=C2N(C(C(O)=O)C)C=CC2=C1OCC1=CC=CC=C1 BLEXBLKEOIMMPG-UHFFFAOYSA-N 0.000 claims description 3
- XWSXEFNSBJDUIT-UHFFFAOYSA-N 2-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]indol-1-yl]propanoic acid Chemical compound C1=CC=C2N(C(C(O)=O)C)C=CC2=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 XWSXEFNSBJDUIT-UHFFFAOYSA-N 0.000 claims description 3
- VKIGBCJHOFIPDQ-UHFFFAOYSA-N 2-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propoxy]indol-1-yl]acetic acid Chemical compound N=1C(CCCOC=2C=3C=CN(CC(O)=O)C=3C=CC=2)=C(C)OC=1C1=CC=CC=C1 VKIGBCJHOFIPDQ-UHFFFAOYSA-N 0.000 claims description 3
- VAPOJLGRWDJCJM-UHFFFAOYSA-N 2-fluoro-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-phenylpropanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(F)(C(O)=O)C1=CC=CC=C1 VAPOJLGRWDJCJM-UHFFFAOYSA-N 0.000 claims description 3
- DQLIENRAYDIVSX-UHFFFAOYSA-N 2-methyl-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-phenylpropanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)C1=CC=CC=C1 DQLIENRAYDIVSX-UHFFFAOYSA-N 0.000 claims description 3
- HQWCDOBDGLODMW-UHFFFAOYSA-N 3-[1-[[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]phenyl]methyl]pyrrol-2-yl]propanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCCC(C=C1)=CC=C1CN1C=CC=C1CCC(O)=O HQWCDOBDGLODMW-UHFFFAOYSA-N 0.000 claims description 3
- KUBUJDCOEBHZLL-UHFFFAOYSA-N 3-[3-iodo-4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-pyrrol-1-ylpropanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C(=C1)I)=CC=C1CC(C(O)=O)N1C=CC=C1 KUBUJDCOEBHZLL-UHFFFAOYSA-N 0.000 claims description 3
- VCFPQLHOIOFLPQ-UHFFFAOYSA-N 3-[4-[2-(1,3-benzothiazol-2-ylsulfanyl)ethoxy]phenyl]-2-pyrrol-1-ylpropanoic acid Chemical compound C=1C=C(OCCSC=2SC3=CC=CC=C3N=2)C=CC=1CC(C(=O)O)N1C=CC=C1 VCFPQLHOIOFLPQ-UHFFFAOYSA-N 0.000 claims description 3
- JLTALXAYGXMGCK-UHFFFAOYSA-N 3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-(2-oxopyrrolidin-1-yl)propanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C(O)=O)N1CCCC1=O JLTALXAYGXMGCK-UHFFFAOYSA-N 0.000 claims description 3
- KBDKOZLJSLJSMV-UHFFFAOYSA-N 3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-pyridin-4-ylpropanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C(O)=O)C1=CC=NC=C1 KBDKOZLJSLJSMV-UHFFFAOYSA-N 0.000 claims description 3
- HBGMBWWOCFYKFE-UHFFFAOYSA-N 3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethylamino]phenyl]-2-pyrrol-1-ylpropanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCNC(C=C1)=CC=C1CC(C(O)=O)N1C=CC=C1 HBGMBWWOCFYKFE-UHFFFAOYSA-N 0.000 claims description 3
- GRQYLQLTEPYGJJ-UHFFFAOYSA-N 3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propoxy]indol-1-yl]propanoic acid Chemical compound N=1C(CCCOC=2C=3C=CN(CCC(O)=O)C=3C=CC=2)=C(C)OC=1C1=CC=CC=C1 GRQYLQLTEPYGJJ-UHFFFAOYSA-N 0.000 claims description 3
- ZPKXDXUAUWDYLI-UHFFFAOYSA-N 3-[6-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]pyridin-3-yl]-2-thiophen-2-ylpropanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(N=C1)=CC=C1CC(C(O)=O)C1=CC=CS1 ZPKXDXUAUWDYLI-UHFFFAOYSA-N 0.000 claims description 3
- 208000031773 Insulin resistance syndrome Diseases 0.000 claims description 3
- FKEBBTHFISDMIS-UHFFFAOYSA-N methyl 2-(1-methylindol-3-yl)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoate Chemical compound C=1N(C)C2=CC=CC=C2C=1C(C(=O)OC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 FKEBBTHFISDMIS-UHFFFAOYSA-N 0.000 claims description 3
- SWJPGJWUTWNRBQ-UHFFFAOYSA-N methyl 3-[4-[2-(1,3-benzothiazol-2-ylsulfanyl)ethoxy]phenyl]-2-pyrrol-1-ylpropanoate Chemical compound C=1C=C(OCCSC=2SC3=CC=CC=C3N=2)C=CC=1CC(C(=O)OC)N1C=CC=C1 SWJPGJWUTWNRBQ-UHFFFAOYSA-N 0.000 claims description 3
- CIGXQPVLJIJZMK-UHFFFAOYSA-N methyl 3-[4-[2-(2-phenylbenzimidazol-1-yl)ethoxy]phenyl]-2-pyrrol-1-ylpropanoate Chemical compound C1=CC=CN1C(C(=O)OC)CC(C=C1)=CC=C1OCCN(C1=CC=CC=C1N=1)C=1C1=CC=CC=C1 CIGXQPVLJIJZMK-UHFFFAOYSA-N 0.000 claims description 3
- MSIHRBPUGKTHGE-UHFFFAOYSA-N methyl 3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]indol-1-yl]propanoate Chemical compound C1=CC=C2N(CCC(=O)OC)C=CC2=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 MSIHRBPUGKTHGE-UHFFFAOYSA-N 0.000 claims description 3
- NUSDXWCCEQWSLA-UHFFFAOYSA-N methyl 3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propanoyl]phenyl]-2-pyrrol-1-ylpropanoate Chemical compound C1=CC=CN1C(C(=O)OC)CC(C=C1)=CC=C1C(=O)CCC(=C(O1)C)N=C1C1=CC=CC=C1 NUSDXWCCEQWSLA-UHFFFAOYSA-N 0.000 claims description 3
- HRIVQGJYYQOKAS-RUZDIDTESA-N (2R)-2-(4-methoxyphenyl)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound COC1=CC=C(C=C1)[C@H](C(=O)O)CC1=CC=C(C=C1)OCCC=1N=C(OC1C)C1=CC=CC=C1 HRIVQGJYYQOKAS-RUZDIDTESA-N 0.000 claims description 2
- YXCMAAXKGPSTAR-AREMUKBSSA-N (2r)-2-(3-bromopyrrol-1-yl)-2-methyl-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound N1([C@@](C)(C(O)=O)CC2=CC=C(C=C2)OCCC=2N=C(OC=2C)C=2C=CC=CC=2)C=CC(Br)=C1 YXCMAAXKGPSTAR-AREMUKBSSA-N 0.000 claims description 2
- CKSWHCPYUWCGNO-LJQANCHMSA-N (2r)-2-(3-bromopyrrol-1-yl)-3-[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]propanoic acid Chemical compound N1([C@@H](C(O)=O)CC2=CC=C(C=C2)OCCN(C)C=2N=CC=CC=2)C=CC(Br)=C1 CKSWHCPYUWCGNO-LJQANCHMSA-N 0.000 claims description 2
- ZEFOVCSPEBJQKA-RUZDIDTESA-N (2r)-2-(3-bromopyrrol-1-yl)-3-[4-[[4-[4-(trifluoromethyl)phenyl]phenyl]methoxy]phenyl]propanoic acid Chemical compound C([C@H](C(=O)O)N1C=C(Br)C=C1)C(C=C1)=CC=C1OCC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 ZEFOVCSPEBJQKA-RUZDIDTESA-N 0.000 claims description 2
- OAAOTHLNRQKEHS-XMMPIXPASA-N (2r)-2-[[4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl]methyl]-2-pyrrol-1-ylbutanoic acid Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1C[C@](CC)(C(O)=O)N1C=CC=C1 OAAOTHLNRQKEHS-XMMPIXPASA-N 0.000 claims description 2
- MIFUUPIHFXOOSP-RUZDIDTESA-N (2r)-2-[[4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl]methyl]-2-pyrrol-1-ylpentanoic acid Chemical compound C([C@](CCC)(C(O)=O)N1C=CC=C1)C(C=C1)=CC=C1OCCC1=CC=C(CC)C=N1 MIFUUPIHFXOOSP-RUZDIDTESA-N 0.000 claims description 2
- WUTIPJUZRSMSAI-QHCPKHFHSA-N (2r)-2-[[4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl]methyl]-3-fluoro-2-pyrrol-1-ylpropanoic acid Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1C[C@](CF)(C(O)=O)N1C=CC=C1 WUTIPJUZRSMSAI-QHCPKHFHSA-N 0.000 claims description 2
- SMRFDNLAHZMZAS-HHHXNRCGSA-N (2r)-2-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methyl]-2-pyrrol-1-ylbutanoic acid Chemical compound C([C@](CC)(C(O)=O)N1C=CC=C1)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 SMRFDNLAHZMZAS-HHHXNRCGSA-N 0.000 claims description 2
- JVRLWDBNZIZBSD-MUUNZHRXSA-N (2r)-2-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methyl]-2-pyrrol-1-ylpentanoic acid Chemical compound C([C@](CCC)(C(O)=O)N1C=CC=C1)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 JVRLWDBNZIZBSD-MUUNZHRXSA-N 0.000 claims description 2
- WUSDIWKLWOXXFM-HSZRJFAPSA-N (2r)-2-[[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]methyl]-2-pyrrol-1-ylbutanoic acid Chemical compound C([C@](CC)(C(O)=O)N1C=CC=C1)C(C=C1)=CC=C1OCCN(C)C1=CC=CC=N1 WUSDIWKLWOXXFM-HSZRJFAPSA-N 0.000 claims description 2
- VYRMZENBWWQWHY-XMMPIXPASA-N (2r)-2-[[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]methyl]-2-pyrrol-1-ylpentanoic acid Chemical compound C([C@](CCC)(C(O)=O)N1C=CC=C1)C(C=C1)=CC=C1OCCN(C)C1=CC=CC=N1 VYRMZENBWWQWHY-XMMPIXPASA-N 0.000 claims description 2
- VHGAQAIHABYFJG-HHHXNRCGSA-N (2r)-2-methyl-2-pyrrol-1-yl-3-[4-[[4-[4-(trifluoromethyl)phenyl]phenyl]methoxy]phenyl]propanoic acid Chemical compound C([C@](C)(C(O)=O)N1C=CC=C1)C(C=C1)=CC=C1OCC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 VHGAQAIHABYFJG-HHHXNRCGSA-N 0.000 claims description 2
- MZEGPXNEXGOJLT-AREMUKBSSA-N (2r)-2-methyl-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-pyrrol-1-ylpropanoic acid Chemical compound N1([C@@](C)(C(O)=O)CC2=CC=C(C=C2)OCCC=2N=C(OC=2C)C=2C=CC=CC=2)C=CC=C1 MZEGPXNEXGOJLT-AREMUKBSSA-N 0.000 claims description 2
- IIAVZJUPQZQTPL-JOCHJYFZSA-N (2r)-2-methyl-3-[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]-2-pyrrol-1-ylpropanoic acid Chemical compound N1([C@@](C)(C(O)=O)CC2=CC=C(C=C2)OCCN(C)C=2N=CC=CC=2)C=CC=C1 IIAVZJUPQZQTPL-JOCHJYFZSA-N 0.000 claims description 2
- UDWLTZGGRKCHPQ-MUUNZHRXSA-N (2r)-2-pyrrol-1-yl-2-[[4-[[4-[4-(trifluoromethyl)phenyl]phenyl]methoxy]phenyl]methyl]butanoic acid Chemical compound C([C@](CC)(C(O)=O)N1C=CC=C1)C(C=C1)=CC=C1OCC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 UDWLTZGGRKCHPQ-MUUNZHRXSA-N 0.000 claims description 2
- GLMGRVOPHFBLPO-GDLZYMKVSA-N (2r)-2-pyrrol-1-yl-2-[[4-[[4-[4-(trifluoromethyl)phenyl]phenyl]methoxy]phenyl]methyl]pentanoic acid Chemical compound C([C@](CCC)(C(O)=O)N1C=CC=C1)C(C=C1)=CC=C1OCC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 GLMGRVOPHFBLPO-GDLZYMKVSA-N 0.000 claims description 2
- IJXRZBCKTMSDBJ-RUZDIDTESA-N (2r)-2-pyrrol-1-yl-3-[4-[[4-[4-(trifluoromethyl)phenyl]phenyl]methoxy]phenyl]propanoic acid Chemical compound C([C@H](C(=O)O)N1C=CC=C1)C(C=C1)=CC=C1OCC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 IJXRZBCKTMSDBJ-RUZDIDTESA-N 0.000 claims description 2
- UBBHVGYLWGNGBH-RUZDIDTESA-N (2r)-3,3,3-trifluoro-2-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methyl]-2-pyrrol-1-ylpropanoic acid Chemical compound N1([C@@](C(O)=O)(CC2=CC=C(C=C2)OCCC=2N=C(OC=2C)C=2C=CC=CC=2)C(F)(F)F)C=CC=C1 UBBHVGYLWGNGBH-RUZDIDTESA-N 0.000 claims description 2
- UAQLCIDHMJBKQS-OAQYLSRUSA-N (2r)-3,3,3-trifluoro-2-[[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]methyl]-2-pyrrol-1-ylpropanoic acid Chemical compound N1([C@@](C(O)=O)(CC2=CC=C(C=C2)OCCN(C)C=2N=CC=CC=2)C(F)(F)F)C=CC=C1 UAQLCIDHMJBKQS-OAQYLSRUSA-N 0.000 claims description 2
- NSWKLDQCWRZABS-AREMUKBSSA-N (2r)-3,3,3-trifluoro-2-pyrrol-1-yl-2-[[4-[[4-[4-(trifluoromethyl)phenyl]phenyl]methoxy]phenyl]methyl]propanoic acid Chemical compound C([C@](C(=O)O)(N1C=CC=C1)C(F)(F)F)C(C=C1)=CC=C1OCC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 NSWKLDQCWRZABS-AREMUKBSSA-N 0.000 claims description 2
- XQUZDXTWRQNTSX-OAQYLSRUSA-N (2r)-3-[4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl]-2-pyrrol-1-ylpropanoic acid Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1C[C@H](C(O)=O)N1C=CC=C1 XQUZDXTWRQNTSX-OAQYLSRUSA-N 0.000 claims description 2
- LMMPCESAYKTJSG-NRFANRHFSA-N (2s)-2-(3-bromopyrrol-1-yl)-3-[4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl]propanoic acid Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1C[C@@H](C(O)=O)N1C=C(Br)C=C1 LMMPCESAYKTJSG-NRFANRHFSA-N 0.000 claims description 2
- CKSWHCPYUWCGNO-IBGZPJMESA-N (2s)-2-(3-bromopyrrol-1-yl)-3-[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]propanoic acid Chemical compound N1([C@H](C(O)=O)CC2=CC=C(C=C2)OCCN(C)C=2N=CC=CC=2)C=CC(Br)=C1 CKSWHCPYUWCGNO-IBGZPJMESA-N 0.000 claims description 2
- OAAOTHLNRQKEHS-DEOSSOPVSA-N (2s)-2-[[4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl]methyl]-2-pyrrol-1-ylbutanoic acid Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1C[C@@](CC)(C(O)=O)N1C=CC=C1 OAAOTHLNRQKEHS-DEOSSOPVSA-N 0.000 claims description 2
- MIFUUPIHFXOOSP-VWLOTQADSA-N (2s)-2-[[4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl]methyl]-2-pyrrol-1-ylpentanoic acid Chemical compound C([C@@](CCC)(C(O)=O)N1C=CC=C1)C(C=C1)=CC=C1OCCC1=CC=C(CC)C=N1 MIFUUPIHFXOOSP-VWLOTQADSA-N 0.000 claims description 2
- WUTIPJUZRSMSAI-HSZRJFAPSA-N (2s)-2-[[4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl]methyl]-3-fluoro-2-pyrrol-1-ylpropanoic acid Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1C[C@@](CF)(C(O)=O)N1C=CC=C1 WUTIPJUZRSMSAI-HSZRJFAPSA-N 0.000 claims description 2
- SMRFDNLAHZMZAS-MHZLTWQESA-N (2s)-2-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methyl]-2-pyrrol-1-ylbutanoic acid Chemical compound C([C@@](CC)(C(O)=O)N1C=CC=C1)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 SMRFDNLAHZMZAS-MHZLTWQESA-N 0.000 claims description 2
- JVRLWDBNZIZBSD-NDEPHWFRSA-N (2s)-2-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methyl]-2-pyrrol-1-ylpentanoic acid Chemical compound C([C@@](CCC)(C(O)=O)N1C=CC=C1)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 JVRLWDBNZIZBSD-NDEPHWFRSA-N 0.000 claims description 2
- WUSDIWKLWOXXFM-QHCPKHFHSA-N (2s)-2-[[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]methyl]-2-pyrrol-1-ylbutanoic acid Chemical compound C([C@@](CC)(C(O)=O)N1C=CC=C1)C(C=C1)=CC=C1OCCN(C)C1=CC=CC=N1 WUSDIWKLWOXXFM-QHCPKHFHSA-N 0.000 claims description 2
- VHGAQAIHABYFJG-MHZLTWQESA-N (2s)-2-methyl-2-pyrrol-1-yl-3-[4-[[4-[4-(trifluoromethyl)phenyl]phenyl]methoxy]phenyl]propanoic acid Chemical compound C([C@@](C)(C(O)=O)N1C=CC=C1)C(C=C1)=CC=C1OCC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 VHGAQAIHABYFJG-MHZLTWQESA-N 0.000 claims description 2
- IIAVZJUPQZQTPL-QFIPXVFZSA-N (2s)-2-methyl-3-[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]-2-pyrrol-1-ylpropanoic acid Chemical compound N1([C@](C)(C(O)=O)CC2=CC=C(C=C2)OCCN(C)C=2N=CC=CC=2)C=CC=C1 IIAVZJUPQZQTPL-QFIPXVFZSA-N 0.000 claims description 2
- UDWLTZGGRKCHPQ-NDEPHWFRSA-N (2s)-2-pyrrol-1-yl-2-[[4-[[4-[4-(trifluoromethyl)phenyl]phenyl]methoxy]phenyl]methyl]butanoic acid Chemical compound C([C@@](CC)(C(O)=O)N1C=CC=C1)C(C=C1)=CC=C1OCC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 UDWLTZGGRKCHPQ-NDEPHWFRSA-N 0.000 claims description 2
- GLMGRVOPHFBLPO-LJAQVGFWSA-N (2s)-2-pyrrol-1-yl-2-[[4-[[4-[4-(trifluoromethyl)phenyl]phenyl]methoxy]phenyl]methyl]pentanoic acid Chemical compound C([C@@](CCC)(C(O)=O)N1C=CC=C1)C(C=C1)=CC=C1OCC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 GLMGRVOPHFBLPO-LJAQVGFWSA-N 0.000 claims description 2
- IJXRZBCKTMSDBJ-VWLOTQADSA-N (2s)-2-pyrrol-1-yl-3-[4-[[4-[4-(trifluoromethyl)phenyl]phenyl]methoxy]phenyl]propanoic acid Chemical compound C([C@@H](C(=O)O)N1C=CC=C1)C(C=C1)=CC=C1OCC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 IJXRZBCKTMSDBJ-VWLOTQADSA-N 0.000 claims description 2
- UBBHVGYLWGNGBH-VWLOTQADSA-N (2s)-3,3,3-trifluoro-2-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methyl]-2-pyrrol-1-ylpropanoic acid Chemical compound N1([C@](C(O)=O)(CC2=CC=C(C=C2)OCCC=2N=C(OC=2C)C=2C=CC=CC=2)C(F)(F)F)C=CC=C1 UBBHVGYLWGNGBH-VWLOTQADSA-N 0.000 claims description 2
- UAQLCIDHMJBKQS-NRFANRHFSA-N (2s)-3,3,3-trifluoro-2-[[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]methyl]-2-pyrrol-1-ylpropanoic acid Chemical compound N1([C@](C(O)=O)(CC2=CC=C(C=C2)OCCN(C)C=2N=CC=CC=2)C(F)(F)F)C=CC=C1 UAQLCIDHMJBKQS-NRFANRHFSA-N 0.000 claims description 2
- NSWKLDQCWRZABS-SANMLTNESA-N (2s)-3,3,3-trifluoro-2-pyrrol-1-yl-2-[[4-[[4-[4-(trifluoromethyl)phenyl]phenyl]methoxy]phenyl]methyl]propanoic acid Chemical compound C([C@@](C(=O)O)(N1C=CC=C1)C(F)(F)F)C(C=C1)=CC=C1OCC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 NSWKLDQCWRZABS-SANMLTNESA-N 0.000 claims description 2
- XQUZDXTWRQNTSX-NRFANRHFSA-N (2s)-3-[4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl]-2-pyrrol-1-ylpropanoic acid Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1C[C@@H](C(O)=O)N1C=CC=C1 XQUZDXTWRQNTSX-NRFANRHFSA-N 0.000 claims description 2
- NXIZZTBLFKHJCV-QHCPKHFHSA-N (2s)-3-[4-[[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methylamino]methyl]phenyl]-2-pyrrol-1-ylpropanoic acid Chemical compound N1([C@H](C(O)=O)CC2=CC=C(C=C2)CNCC=2N=C(OC=2C)C=2C=CC=CC=2)C=CC=C1 NXIZZTBLFKHJCV-QHCPKHFHSA-N 0.000 claims description 2
- FGJSMYVPWUZNMM-DEOSSOPVSA-N (2s)-3-[4-[[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethylamino]methyl]phenyl]-2-pyrrol-1-ylpropanoic acid Chemical compound N1([C@H](C(O)=O)CC2=CC=C(C=C2)CNCCC=2N=C(OC=2C)C=2C=CC=CC=2)C=CC=C1 FGJSMYVPWUZNMM-DEOSSOPVSA-N 0.000 claims description 2
- QWVMMWLVLYZWJO-VWLOTQADSA-N (2s)-3-[4-[[acetyl-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methyl]amino]methyl]phenyl]-2-pyrrol-1-ylpropanoic acid Chemical compound C=1C=C(C[C@@H](C(O)=O)N2C=CC=C2)C=CC=1CN(C(=O)C)CC(=C(O1)C)N=C1C1=CC=CC=C1 QWVMMWLVLYZWJO-VWLOTQADSA-N 0.000 claims description 2
- QBSRHWLRYLSOAB-SANMLTNESA-N (2s)-3-[4-[[acetyl-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethyl]amino]methyl]phenyl]-2-pyrrol-1-ylpropanoic acid Chemical compound C=1C=C(C[C@@H](C(O)=O)N2C=CC=C2)C=CC=1CN(C(=O)C)CCC(=C(O1)C)N=C1C1=CC=CC=C1 QBSRHWLRYLSOAB-SANMLTNESA-N 0.000 claims description 2
- FCXQPXFVLDZXHP-DEOSSOPVSA-N (2s)-3-[4-[[methyl-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methyl]amino]methyl]phenyl]-2-pyrrol-1-ylpropanoic acid Chemical compound C=1C=C(C[C@@H](C(O)=O)N2C=CC=C2)C=CC=1CN(C)CC(=C(O1)C)N=C1C1=CC=CC=C1 FCXQPXFVLDZXHP-DEOSSOPVSA-N 0.000 claims description 2
- MFMKMCYXEFZRGM-UHFFFAOYSA-N 2-(3-methyl-1,2-oxazol-5-yl)-3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]phenyl]propanoic acid Chemical compound O1N=C(C)C=C1C(C(O)=O)CC(C=C1)=CC=C1CCCC1=C(C)OC(C=2C=CC=CC=2)=N1 MFMKMCYXEFZRGM-UHFFFAOYSA-N 0.000 claims description 2
- QDBMFRPMKUDTGG-UHFFFAOYSA-N 2-(5-methyl-1,2-oxazol-3-yl)-3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]phenyl]propanoic acid Chemical compound O1C(C)=CC(C(CC=2C=CC(CCCC3=C(OC(=N3)C=3C=CC=CC=3)C)=CC=2)C(O)=O)=N1 QDBMFRPMKUDTGG-UHFFFAOYSA-N 0.000 claims description 2
- AKIGVDRXHAKLLX-AREMUKBSSA-N 2-[(1r)-2-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-1-pyrrol-1-ylethyl]-5-propyl-1,3,4-oxadiazole Chemical compound O1C(CCC)=NN=C1[C@H](N1C=CC=C1)CC(C=C1)=CC=C1OCCC1=C(C)OC(C=2C=CC=CC=2)=N1 AKIGVDRXHAKLLX-AREMUKBSSA-N 0.000 claims description 2
- XDVYBSONSPJXRD-RUZDIDTESA-N 2-ethyl-5-[(1r)-2-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-1-pyrrol-1-ylethyl]-1,3,4-oxadiazole Chemical compound O1C(CC)=NN=C1[C@H](N1C=CC=C1)CC(C=C1)=CC=C1OCCC1=C(C)OC(C=2C=CC=CC=2)=N1 XDVYBSONSPJXRD-RUZDIDTESA-N 0.000 claims description 2
- DEZHCFWQUKTXRE-UHFFFAOYSA-N 3-[1-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]piperidin-4-yl]-2-pyrrol-1-ylpropanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCCN(CC1)CCC1CC(C(O)=O)N1C=CC=C1 DEZHCFWQUKTXRE-UHFFFAOYSA-N 0.000 claims description 2
- OMSPUVWUIHNYCS-UHFFFAOYSA-N 3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]indol-1-yl]propanoic acid Chemical compound N=1C(CCOC=2C=3C=CN(CCC(O)=O)C=3C=CC=2)=C(C)OC=1C1=CC=CC=C1 OMSPUVWUIHNYCS-UHFFFAOYSA-N 0.000 claims description 2
- FKWSTDFHAXMAIN-UHFFFAOYSA-N 3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)prop-1-ynyl]phenyl]-2-(4-phenylphenyl)propanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CC#CC(C=C1)=CC=C1CC(C(O)=O)C(C=C1)=CC=C1C1=CC=CC=C1 FKWSTDFHAXMAIN-UHFFFAOYSA-N 0.000 claims description 2
- XVJXEKYLXFKVRG-UHFFFAOYSA-N 3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]phenyl]-2-(1,2,4-triazol-1-yl)propanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCCC(C=C1)=CC=C1CC(C(O)=O)N1C=NC=N1 XVJXEKYLXFKVRG-UHFFFAOYSA-N 0.000 claims description 2
- QEVQBINBSHZTPY-UHFFFAOYSA-N 3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]phenyl]-2-(3-phenylphenyl)propanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCCC(C=C1)=CC=C1CC(C(O)=O)C(C=1)=CC=CC=1C1=CC=CC=C1 QEVQBINBSHZTPY-UHFFFAOYSA-N 0.000 claims description 2
- YCJCCXANVWILMI-UHFFFAOYSA-N 3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]phenyl]-2-(4-phenylphenyl)propanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCCC(C=C1)=CC=C1CC(C(O)=O)C(C=C1)=CC=C1C1=CC=CC=C1 YCJCCXANVWILMI-UHFFFAOYSA-N 0.000 claims description 2
- RCUTXJICVDHZFT-UHFFFAOYSA-N 3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]phenyl]-2-pyrazol-1-ylpropanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCCC(C=C1)=CC=C1CC(C(O)=O)N1C=CC=N1 RCUTXJICVDHZFT-UHFFFAOYSA-N 0.000 claims description 2
- YMFQNBCCQXQJJS-UHFFFAOYSA-N 3-[5-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]naphthalen-1-yl]-2-pyrrol-1-ylpropanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCCC(C1=CC=C2)=CC=CC1=C2CC(C(O)=O)N1C=CC=C1 YMFQNBCCQXQJJS-UHFFFAOYSA-N 0.000 claims description 2
- AMYJOMVITVSQGG-UHFFFAOYSA-N 3-[6-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]pyridin-3-yl]-2-pyrrol-1-ylpropanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(N=C1)=CC=C1CC(C(O)=O)N1C=CC=C1 AMYJOMVITVSQGG-UHFFFAOYSA-N 0.000 claims description 2
- OVCOTTFEAZSMCD-UHFFFAOYSA-N 6-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]naphthalene-2-carboxylic acid Chemical compound N=1C(CCOC=2C=C3C=CC(=CC3=CC=2)C(O)=O)=C(C)OC=1C1=CC=CC=C1 OVCOTTFEAZSMCD-UHFFFAOYSA-N 0.000 claims description 2
- QDHFHIQKOVNCNC-UHFFFAOYSA-N butane-1-sulfonic acid Chemical compound CCCCS(O)(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- BCAKKAXGSIBALM-HHHXNRCGSA-N ethyl (2r)-3,3,3-trifluoro-2-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methyl]-2-pyrrol-1-ylpropanoate Chemical compound C([C@](C(=O)OCC)(N1C=CC=C1)C(F)(F)F)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 BCAKKAXGSIBALM-HHHXNRCGSA-N 0.000 claims description 2
- JPGOTNABVBACTB-HSZRJFAPSA-N ethyl (2r)-3,3,3-trifluoro-2-[[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]methyl]-2-pyrrol-1-ylpropanoate Chemical compound C([C@](C(=O)OCC)(N1C=CC=C1)C(F)(F)F)C(C=C1)=CC=C1OCCN(C)C1=CC=CC=N1 JPGOTNABVBACTB-HSZRJFAPSA-N 0.000 claims description 2
- BCAKKAXGSIBALM-MHZLTWQESA-N ethyl (2s)-3,3,3-trifluoro-2-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methyl]-2-pyrrol-1-ylpropanoate Chemical compound C([C@@](C(=O)OCC)(N1C=CC=C1)C(F)(F)F)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 BCAKKAXGSIBALM-MHZLTWQESA-N 0.000 claims description 2
- ABHKJODSGFHICX-NDEPHWFRSA-N ethyl (2s)-3,3,3-trifluoro-2-pyrrol-1-yl-2-[[4-[[4-[4-(trifluoromethyl)phenyl]phenyl]methoxy]phenyl]methyl]propanoate Chemical compound C([C@@](C(=O)OCC)(N1C=CC=C1)C(F)(F)F)C(C=C1)=CC=C1OCC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 ABHKJODSGFHICX-NDEPHWFRSA-N 0.000 claims description 2
- MBGKJSSWGKZRCK-UHFFFAOYSA-N ethyl 3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]phenyl]-2-(triazol-1-yl)propanoate Chemical compound C1=CN=NN1C(C(=O)OCC)CC(C=C1)=CC=C1CCCC(=C(O1)C)N=C1C1=CC=CC=C1 MBGKJSSWGKZRCK-UHFFFAOYSA-N 0.000 claims description 2
- BCHZZDZKPFFPAK-AREMUKBSSA-N methyl (2R)-2-(4-methoxyphenyl)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoate Chemical compound COC([C@H](CC1=CC=C(C=C1)OCCC=1N=C(OC1C)C1=CC=CC=C1)C1=CC=C(C=C1)OC)=O BCHZZDZKPFFPAK-AREMUKBSSA-N 0.000 claims description 2
- JLIWNAJXMOPWMH-RUZDIDTESA-N methyl (2r)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-phenylpropanoate Chemical compound C([C@@H](C(=O)OC)C=1C=CC=CC=1)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 JLIWNAJXMOPWMH-RUZDIDTESA-N 0.000 claims description 2
- VSTVBNAOHVNEPR-QFIPXVFZSA-N methyl (2s)-2-(2,5-dimethylpyrrol-1-yl)-3-[4-[(2-fluorophenyl)methoxy]phenyl]propanoate Chemical compound C([C@@H](C(=O)OC)N1C(=CC=C1C)C)C(C=C1)=CC=C1OCC1=CC=CC=C1F VSTVBNAOHVNEPR-QFIPXVFZSA-N 0.000 claims description 2
- JVRDFZDVBRLHCZ-QHCPKHFHSA-N methyl (2s)-3-[3-fluoro-4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-pyrrol-1-ylpropanoate Chemical compound C([C@@H](C(=O)OC)N1C=CC=C1)C(C=C1F)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 JVRDFZDVBRLHCZ-QHCPKHFHSA-N 0.000 claims description 2
- CRXOZEHIXBBDFA-VWLOTQADSA-N methyl (2s)-3-[4-[2-[(7-chloroquinolin-4-yl)-methylamino]ethoxy]phenyl]-2-pyrrol-1-ylpropanoate Chemical compound N1([C@@H](CC=2C=CC(OCCN(C)C=3C4=CC=C(Cl)C=C4N=CC=3)=CC=2)C(=O)OC)C=CC=C1 CRXOZEHIXBBDFA-VWLOTQADSA-N 0.000 claims description 2
- KMWATNKKCRSURJ-MHZLTWQESA-N methyl (2s)-3-[4-[2-[1,3-benzoxazol-2-yl(methyl)amino]ethoxy]phenyl]-2-(3-phenylpyrrol-1-yl)propanoate Chemical compound C=1N([C@@H](CC=2C=CC(OCCN(C)C=3OC4=CC=CC=C4N=3)=CC=2)C(=O)OC)C=CC=1C1=CC=CC=C1 KMWATNKKCRSURJ-MHZLTWQESA-N 0.000 claims description 2
- IVIPYRPBIQZLCX-DEOSSOPVSA-N methyl (2s)-3-[4-[[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methylamino]methyl]phenyl]-2-pyrrol-1-ylpropanoate Chemical compound C([C@@H](C(=O)OC)N1C=CC=C1)C(C=C1)=CC=C1CNCC(=C(O1)C)N=C1C1=CC=CC=C1 IVIPYRPBIQZLCX-DEOSSOPVSA-N 0.000 claims description 2
- IGRARXMIVODCPQ-SANMLTNESA-N methyl (2s)-3-[4-[[acetyl-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methyl]amino]methyl]phenyl]-2-pyrrol-1-ylpropanoate Chemical compound C([C@@H](C(=O)OC)N1C=CC=C1)C(C=C1)=CC=C1CN(C(C)=O)CC(=C(O1)C)N=C1C1=CC=CC=C1 IGRARXMIVODCPQ-SANMLTNESA-N 0.000 claims description 2
- VEKLRMYAYHFKMJ-VWLOTQADSA-N methyl (2s)-3-[4-[[methyl-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methyl]amino]methyl]phenyl]-2-pyrrol-1-ylpropanoate Chemical compound C([C@@H](C(=O)OC)N1C=CC=C1)C(C=C1)=CC=C1CN(C)CC(=C(O1)C)N=C1C1=CC=CC=C1 VEKLRMYAYHFKMJ-VWLOTQADSA-N 0.000 claims description 2
- GDMRHUUVDXUYPB-UHFFFAOYSA-N methyl 2,2-dimethyl-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(C)(C)C(=O)OC)=CC=C1OCCC1=C(C)OC(C=2C=CC=CC=2)=N1 GDMRHUUVDXUYPB-UHFFFAOYSA-N 0.000 claims description 2
- UUEVWSYHVRHFJN-UHFFFAOYSA-N methyl 2-(2-bromopyrrol-1-yl)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoate Chemical compound C1=CC=C(Br)N1C(C(=O)OC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 UUEVWSYHVRHFJN-UHFFFAOYSA-N 0.000 claims description 2
- BBVJCHWZJRWOQS-UHFFFAOYSA-N methyl 2-(3-bromopyrrol-1-yl)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoate Chemical compound C1=CC(Br)=CN1C(C(=O)OC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 BBVJCHWZJRWOQS-UHFFFAOYSA-N 0.000 claims description 2
- ZNSSRQQTBPKTSL-UHFFFAOYSA-N methyl 2-(3-methyl-1,2-oxazol-5-yl)-3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]phenyl]propanoate Chemical compound C=1C(C)=NOC=1C(C(=O)OC)CC(C=C1)=CC=C1CCCC(=C(O1)C)N=C1C1=CC=CC=C1 ZNSSRQQTBPKTSL-UHFFFAOYSA-N 0.000 claims description 2
- HNAHEGWPMXCIOE-UHFFFAOYSA-N methyl 2-(4-phenylmethoxyindol-1-yl)propanoate Chemical compound C1=CC=C2N(C(C)C(=O)OC)C=CC2=C1OCC1=CC=CC=C1 HNAHEGWPMXCIOE-UHFFFAOYSA-N 0.000 claims description 2
- LFTRIEUINWGBIC-UHFFFAOYSA-N methyl 2-(5-methyl-1,2-oxazol-3-yl)-3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]phenyl]propanoate Chemical compound C1=C(C)ON=C1C(C(=O)OC)CC(C=C1)=CC=C1CCCC(=C(O1)C)N=C1C1=CC=CC=C1 LFTRIEUINWGBIC-UHFFFAOYSA-N 0.000 claims description 2
- ZTNCSNCWVUJCMZ-UHFFFAOYSA-N methyl 2-[1-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethyl]indol-5-yl]oxy-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C(=O)OC)OC(C=C1C=C2)=CC=C1N2CCC(=C(O1)C)N=C1C1=CC=CC=C1 ZTNCSNCWVUJCMZ-UHFFFAOYSA-N 0.000 claims description 2
- DWBMCDPFRZRNHM-UHFFFAOYSA-N methyl 2-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]indol-1-yl]propanoate Chemical compound C1=CC=C2N(C(C)C(=O)OC)C=CC2=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 DWBMCDPFRZRNHM-UHFFFAOYSA-N 0.000 claims description 2
- OMSWZTQKOYECEX-UHFFFAOYSA-N methyl 2-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propoxy]indol-1-yl]acetate Chemical compound C1=CC=C2N(CC(=O)OC)C=CC2=C1OCCCC(=C(O1)C)N=C1C1=CC=CC=C1 OMSWZTQKOYECEX-UHFFFAOYSA-N 0.000 claims description 2
- RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 claims description 2
- LXMAJAAIKGSJBS-UHFFFAOYSA-N methyl 2-fluoro-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-phenylpropanoate Chemical compound C=1C=CC=CC=1C(F)(C(=O)OC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 LXMAJAAIKGSJBS-UHFFFAOYSA-N 0.000 claims description 2
- FYPHXZLJZNLRHR-UHFFFAOYSA-N methyl 2-methyl-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-phenylpropanoate Chemical compound C=1C=CC=CC=1C(C)(C(=O)OC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 FYPHXZLJZNLRHR-UHFFFAOYSA-N 0.000 claims description 2
- UIDTYKMUNUBIOI-UHFFFAOYSA-N methyl 2-methyl-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-thiophen-2-ylpropanoate Chemical compound C=1C=CSC=1C(C)(C(=O)OC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 UIDTYKMUNUBIOI-UHFFFAOYSA-N 0.000 claims description 2
- XEKFQBOQHYCZNM-UHFFFAOYSA-N methyl 2-methyl-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-thiophen-3-ylpropanoate Chemical compound C1=CSC=C1C(C)(C(=O)OC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 XEKFQBOQHYCZNM-UHFFFAOYSA-N 0.000 claims description 2
- JTODKZAGWGQVKC-UHFFFAOYSA-N methyl 3,3,3-trifluoro-2-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methyl]-2-pyrrol-1-ylpropanoate Chemical compound C1=CC=CN1C(C(F)(F)F)(C(=O)OC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 JTODKZAGWGQVKC-UHFFFAOYSA-N 0.000 claims description 2
- HYZLZBBTGQHGFY-UHFFFAOYSA-N methyl 3-[3-methoxy-4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)prop-1-enyl]phenyl]-2-pyrrol-1-ylpropanoate Chemical compound C1=CC=CN1C(C(=O)OC)CC(C=C1OC)=CC=C1C=CCC(=C(O1)C)N=C1C1=CC=CC=C1 HYZLZBBTGQHGFY-UHFFFAOYSA-N 0.000 claims description 2
- MVOXUVNEANHPDN-UHFFFAOYSA-N methyl 3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-(2-oxopyrrolidin-1-yl)propanoate Chemical compound C1CCC(=O)N1C(C(=O)OC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 MVOXUVNEANHPDN-UHFFFAOYSA-N 0.000 claims description 2
- XSYBSMOBMQYFPY-UHFFFAOYSA-N methyl 3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C(C(=O)OC)=CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 XSYBSMOBMQYFPY-UHFFFAOYSA-N 0.000 claims description 2
- JEUFTGGGEYUILF-UHFFFAOYSA-N methyl 3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-thiophen-2-ylpropanoate Chemical compound C=1C=CSC=1C(C(=O)OC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 JEUFTGGGEYUILF-UHFFFAOYSA-N 0.000 claims description 2
- AYTVEPOPSWRRCA-UHFFFAOYSA-N methyl 3-[4-[2-[2-(trifluoromethyl)phenyl]ethoxy]indol-1-yl]propanoate Chemical compound C1=CC=C2N(CCC(=O)OC)C=CC2=C1OCCC1=CC=CC=C1C(F)(F)F AYTVEPOPSWRRCA-UHFFFAOYSA-N 0.000 claims description 2
- TZTUBSQVHCTDKP-UHFFFAOYSA-N methyl 3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)prop-1-ynyl]phenyl]-2-(4-phenylphenyl)propanoate Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(C(=O)OC)CC(C=C1)=CC=C1C#CCC(=C(O1)C)N=C1C1=CC=CC=C1 TZTUBSQVHCTDKP-UHFFFAOYSA-N 0.000 claims description 2
- MDAJOKXOBMUDDR-UHFFFAOYSA-N methyl 3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propoxy]indol-1-yl]propanoate Chemical compound C1=CC=C2N(CCC(=O)OC)C=CC2=C1OCCCC(=C(O1)C)N=C1C1=CC=CC=C1 MDAJOKXOBMUDDR-UHFFFAOYSA-N 0.000 claims description 2
- IBKCNJBAZQDTDZ-UHFFFAOYSA-N methyl 3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]phenyl]-2-(1,2,4-triazol-1-yl)propanoate Chemical compound C1=NC=NN1C(C(=O)OC)CC(C=C1)=CC=C1CCCC(=C(O1)C)N=C1C1=CC=CC=C1 IBKCNJBAZQDTDZ-UHFFFAOYSA-N 0.000 claims description 2
- ZDUNLAYLPXIXOI-UHFFFAOYSA-N methyl 3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]phenyl]-2-(3-phenylphenyl)propanoate Chemical compound C=1C=CC(C=2C=CC=CC=2)=CC=1C(C(=O)OC)CC(C=C1)=CC=C1CCCC(=C(O1)C)N=C1C1=CC=CC=C1 ZDUNLAYLPXIXOI-UHFFFAOYSA-N 0.000 claims description 2
- PHHFJDRJOPDJQT-UHFFFAOYSA-N methyl 3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]phenyl]-2-(4-phenylphenyl)propanoate Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(C(=O)OC)CC(C=C1)=CC=C1CCCC(=C(O1)C)N=C1C1=CC=CC=C1 PHHFJDRJOPDJQT-UHFFFAOYSA-N 0.000 claims description 2
- AEURJBHFEQGQIV-UHFFFAOYSA-N methyl 3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]phenyl]-2-(triazol-1-yl)propanoate Chemical compound C1=CN=NN1C(C(=O)OC)CC(C=C1)=CC=C1CCCC(=C(O1)C)N=C1C1=CC=CC=C1 AEURJBHFEQGQIV-UHFFFAOYSA-N 0.000 claims description 2
- LSYODSWEGIBKLB-UHFFFAOYSA-N methyl 3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]phenyl]-2-pyrazol-1-ylpropanoate Chemical compound C1=CC=NN1C(C(=O)OC)CC(C=C1)=CC=C1CCCC(=C(O1)C)N=C1C1=CC=CC=C1 LSYODSWEGIBKLB-UHFFFAOYSA-N 0.000 claims description 2
- KOCSJIQHWZPPQQ-UHFFFAOYSA-N methyl 3-[5-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]naphthalen-1-yl]-2-pyrrol-1-ylpropanoate Chemical compound C1=CC=CN1C(C(=O)OC)CC(C1=CC=C2)=CC=CC1=C2CCCC(=C(O1)C)N=C1C1=CC=CC=C1 KOCSJIQHWZPPQQ-UHFFFAOYSA-N 0.000 claims description 2
- YZCLEXQBHWULKZ-UHFFFAOYSA-N methyl 3-[6-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]pyridin-3-yl]-2-pyrrol-1-ylpropanoate Chemical compound C1=CC=CN1C(C(=O)OC)CC(C=N1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 YZCLEXQBHWULKZ-UHFFFAOYSA-N 0.000 claims description 2
- YEUFJUPSEXWEKQ-UHFFFAOYSA-N methyl 3-[6-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]pyridin-3-yl]-2-thiophen-2-ylpropanoate Chemical compound C=1C=CSC=1C(C(=O)OC)CC(C=N1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 YEUFJUPSEXWEKQ-UHFFFAOYSA-N 0.000 claims description 2
- YZHQTKBVYDAUEM-UHFFFAOYSA-N methyl 4-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]indol-1-yl]butanoate Chemical compound C1=CC=C2N(CCCC(=O)OC)C=CC2=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 YZHQTKBVYDAUEM-UHFFFAOYSA-N 0.000 claims description 2
- WUPNNAHAHBIKKO-UHFFFAOYSA-N methyl 6-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]naphthalene-2-carboxylate Chemical compound C1=CC2=CC(C(=O)OC)=CC=C2C=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 WUPNNAHAHBIKKO-UHFFFAOYSA-N 0.000 claims description 2
- 238000012544 monitoring process Methods 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- PMEZHSWQITXLIB-UHFFFAOYSA-N Cc1oc(nc1CCC(=O)c1ccc(CC(C(O)=O)n2cccc2)cc1)-c1ccccc1.CCc1nnc(o1)C(Cc1ccc(OCCc2nc(oc2C)-c2ccccc2)cc1)c1ccccc1 Chemical compound Cc1oc(nc1CCC(=O)c1ccc(CC(C(O)=O)n2cccc2)cc1)-c1ccccc1.CCc1nnc(o1)C(Cc1ccc(OCCc2nc(oc2C)-c2ccccc2)cc1)c1ccccc1 PMEZHSWQITXLIB-UHFFFAOYSA-N 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
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- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Substances C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 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
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Classifications
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- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- C07D207/327—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
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- 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
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- 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
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/38—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms one oxygen atom in position 2 or 4, e.g. pyrones
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- 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
- C07D403/12—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 chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
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- 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
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- 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
- C07D413/12—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 chain containing hetero atoms as chain links
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- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- 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
- C07D417/12—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 chain containing hetero atoms as chain links
Landscapes
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- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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WO2003059907A1 (fr) * | 2002-01-17 | 2003-07-24 | Takeda Chemical Industries, Ltd. | Composes heterocycliques azotes : procede de preparation et d'utilisation |
PA8594401A1 (es) * | 2003-02-21 | 2004-09-16 | Pfizer | Acidos carboxilicos de heteroarilo condensado como agonista del ppar |
JP4828414B2 (ja) * | 2003-04-28 | 2011-11-30 | ニツポネツクス・インコーポレーテツド | インドール酢酸誘導体および薬剤としてのそれらの使用 |
MXPA05013579A (es) * | 2003-06-27 | 2006-03-09 | Warner Lambert Co | Preparacion de 1,2,3-triazoles alquilados en n2. |
WO2005005423A1 (en) * | 2003-07-02 | 2005-01-20 | F. Hoffmann-La Roche Ag | Indolyl derivatives substituted with a thiazole ring and their use as ppar modulators |
NZ545326A (en) * | 2003-07-17 | 2009-12-24 | Plexxikon Inc | PPAR active compounds |
JP2007509996A (ja) * | 2003-11-05 | 2007-04-19 | エフ.ホフマン−ラ ロシュ アーゲー | Ppar活性化剤としてのヘテロアリール誘導体 |
WO2005056522A2 (en) | 2003-12-04 | 2005-06-23 | National Health Research Institutes | Indole compounds |
FR2863610B1 (fr) * | 2003-12-11 | 2006-01-20 | Galderma Res & Dev | NOUVEAUX COMPOSES MODULATEURS DES RECEPTEURS DE TYPE PPARs ET LEUR UTILISATION DANS DES COMPOSITIONS COSMETIQUES OU PHARMACEUTIQUES |
ATE359284T1 (de) * | 2003-12-11 | 2007-05-15 | Galderma Res & Dev | Neue verbindungen, bei denen es sich um modulatoren von rezeptoren vom ppar-typ handelt, und deren verwendung in kosmetischen oder pharmazeutischen zusammensetzungen |
RU2006126978A (ru) | 2003-12-25 | 2008-01-27 | Такеда Фармасьютикал Компани Лимитед (Jp) | Производные 3-(4-бензилоксифенил)пропановой кислоты |
WO2005085235A1 (en) * | 2004-03-09 | 2005-09-15 | F. Hoffmann-La Roche Ag | Pyrazolyl indolyl derivatives as ppar activators |
US7405236B2 (en) * | 2004-08-16 | 2008-07-29 | Hoffman-La Roche Inc. | Indole derivatives comprising an acetylene group |
TW200724138A (en) * | 2005-03-29 | 2007-07-01 | Sk Corp | Substituted carboxylic acid derivatives for the treatment of diabetes and lipid disorders, their preparation and use |
PE20080188A1 (es) * | 2006-04-18 | 2008-03-10 | Janssen Pharmaceutica Nv | Derivados del acido benzoazepin-oxi-acetico como agonistas de ppar-delta usados para aumentar hdl-c, reducir ldl-c y reducir colesterol |
CN102643248A (zh) | 2006-04-18 | 2012-08-22 | 日本化学医药株式会社 | 过氧化物酶体增殖剂激活受体δ的激活剂 |
AU2013202514B2 (en) * | 2006-04-18 | 2015-09-17 | Nippon Chemiphar Co., Ltd. | Activating agent for peroxisome proliferator activated receptor delta |
CN102083810B (zh) | 2008-04-15 | 2014-10-29 | 日本化学医药株式会社 | 过氧化物酶体增殖剂活化受体的活化剂 |
FR2976943B1 (fr) * | 2011-06-23 | 2013-07-12 | Metabolys | Derives de piperazine, leurs procedes de preparation et leurs utilisations dans le traitement de l'insulinoresistance |
FR2976942B1 (fr) * | 2011-06-23 | 2013-07-12 | Metabolys | Derives de piperazine, leurs procedes de preparation et leurs utilisations dans le traitement de l'insulinoresistance |
WO2013139341A1 (en) * | 2012-03-20 | 2013-09-26 | Syddansk Universitet | Gpr120 receptor modulators |
WO2013185766A1 (en) * | 2012-06-15 | 2013-12-19 | Syddansk Universitet | Gpr120 receptor modulators |
Family Cites Families (6)
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WO1999046232A1 (fr) * | 1998-03-10 | 1999-09-16 | Ono Pharmaceutical Co., Ltd. | Derives d'acide carboxylique et medicaments contenant ces derives comme principe actif |
AU1120599A (en) * | 1998-04-23 | 1999-03-08 | Dr. Reddy's Research Foundation | New heterocyclic compounds and their use in medicine, process for their reparation and pharmaceutical compositions containing them |
WO2000023425A1 (en) * | 1998-10-21 | 2000-04-27 | Novo Nordisk A/S | New compounds, their preparation and use |
US6274608B1 (en) * | 1999-04-20 | 2001-08-14 | Novo Nordisk A/S | Compounds, their preparation and use |
IL146104A0 (en) * | 1999-04-28 | 2002-07-25 | Reddy Research Foundation | Substituted bicyclic heterocyclic compounds, processes for their preparation and pharmaceutical compositions containing the same |
ES2215719T3 (es) * | 1999-09-08 | 2004-10-16 | Glaxo Group Limited | Antagonista ppar oxazol. |
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