OA12653A - Oral antidiabetic agents. - Google Patents
Oral antidiabetic agents. Download PDFInfo
- Publication number
- OA12653A OA12653A OA1200400053A OA1200400053A OA12653A OA 12653 A OA12653 A OA 12653A OA 1200400053 A OA1200400053 A OA 1200400053A OA 1200400053 A OA1200400053 A OA 1200400053A OA 12653 A OA12653 A OA 12653A
- Authority
- OA
- OAPI
- Prior art keywords
- phenyl
- methyl
- propionic acid
- oxazol
- ethoxy
- Prior art date
Links
- 239000003538 oral antidiabetic agent Substances 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 326
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 29
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 325
- 229940095574 propionic acid Drugs 0.000 claims description 299
- 125000001072 heteroaryl group Chemical group 0.000 claims description 166
- -1 (Cj-C^alkyl Chemical group 0.000 claims description 137
- 150000002148 esters Chemical class 0.000 claims description 132
- 125000000217 alkyl group Chemical group 0.000 claims description 61
- 150000004702 methyl esters Chemical class 0.000 claims description 56
- 239000002253 acid Substances 0.000 claims description 54
- 125000003118 aryl group Chemical group 0.000 claims description 50
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 42
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 42
- 125000005843 halogen group Chemical group 0.000 claims description 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- 125000003107 substituted aryl group Chemical group 0.000 claims description 32
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 claims description 29
- 241000124008 Mammalia Species 0.000 claims description 29
- 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 28
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 28
- 239000008103 glucose Substances 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 125000004429 atom Chemical group 0.000 claims description 26
- 235000019260 propionic acid Nutrition 0.000 claims description 26
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 22
- 102000004877 Insulin Human genes 0.000 claims description 21
- 108090001061 Insulin Proteins 0.000 claims description 21
- 230000000694 effects Effects 0.000 claims description 21
- 229940125396 insulin Drugs 0.000 claims description 21
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 20
- 125000001589 carboacyl group Chemical group 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 16
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 15
- 229960000583 acetic acid Drugs 0.000 claims description 14
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 14
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 10
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 9
- FNIFVUOVNBTWEC-UHFFFAOYSA-N 5-methyl-2-phenyl-4-prop-2-enyl-1,3-oxazole Chemical compound C=CCC1=C(C)OC(C=2C=CC=CC=2)=N1 FNIFVUOVNBTWEC-UHFFFAOYSA-N 0.000 claims description 9
- 239000008280 blood Substances 0.000 claims description 9
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 9
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 claims description 8
- 210000004369 blood Anatomy 0.000 claims description 8
- 101100134922 Gallus gallus COR5 gene Proteins 0.000 claims description 7
- 210000001789 adipocyte Anatomy 0.000 claims description 7
- 201000001421 hyperglycemia Diseases 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 229960003424 phenylacetic acid Drugs 0.000 claims description 7
- 239000003279 phenylacetic acid Substances 0.000 claims description 7
- MTHRJNLVFAQKOG-UHFFFAOYSA-N 2-pyrrol-1-ylpropanoic acid Chemical compound OC(=O)C(C)N1C=CC=C1 MTHRJNLVFAQKOG-UHFFFAOYSA-N 0.000 claims description 5
- 201000001320 Atherosclerosis Diseases 0.000 claims description 5
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 5
- 208000008589 Obesity Diseases 0.000 claims description 5
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims description 5
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 230000003301 hydrolyzing effect Effects 0.000 claims description 5
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims description 5
- 201000008980 hyperinsulinism Diseases 0.000 claims description 5
- 235000020824 obesity Nutrition 0.000 claims description 5
- 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 claims description 5
- 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 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
- 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 4
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- VNTMTYITVOQQIR-UHFFFAOYSA-N methyl 2-pyrrol-1-ylpropanoate Chemical compound COC(=O)C(C)N1C=CC=C1 VNTMTYITVOQQIR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 208000011580 syndromic disease Diseases 0.000 claims description 4
- 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
- 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 3
- 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 3
- IEXPHZCNSAFOEU-UHFFFAOYSA-N 5-methyl-4-[2-[4-[2-(1-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)C1=NN=NN1C IEXPHZCNSAFOEU-UHFFFAOYSA-N 0.000 claims description 3
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 3
- QDHFHIQKOVNCNC-UHFFFAOYSA-N butane-1-sulfonic acid Chemical compound CCCCS(O)(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000004494 ethyl ester group Chemical group 0.000 claims description 3
- 208000006575 hypertriglyceridemia Diseases 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
- 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 3
- ZAXQRWRRNPKBNK-UHFFFAOYSA-N methyl butane-1-sulfonate Chemical compound CCCCS(=O)(=O)OC ZAXQRWRRNPKBNK-UHFFFAOYSA-N 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 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
- 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 2
- 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 2
- 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 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
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- KTKWUKAYWFMQSO-UHFFFAOYSA-N 2-thiophen-2-ylpropanoic acid Chemical compound OC(=O)C(C)C1=CC=CS1 KTKWUKAYWFMQSO-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- RDGUPGNPYHNTOP-UHFFFAOYSA-N 3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]phenyl]-2-pyrrol-1-ylpropanamide Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCCC(C=C1)=CC=C1CC(C(N)=O)N1C=CC=C1 RDGUPGNPYHNTOP-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
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 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
- ZDCRPTFQQADKKD-SANMLTNESA-N methyl (2s)-2-(2-acetylpyrrol-1-yl)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoate Chemical compound C([C@@H](C(=O)OC)N1C(=CC=C1)C(C)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 ZDCRPTFQQADKKD-SANMLTNESA-N 0.000 claims description 2
- ZHJVRXSCJHSGSY-VWLOTQADSA-N methyl (2s)-3-[4-[2-(4-phenylpiperazin-1-yl)ethoxy]phenyl]-2-pyrrol-1-ylpropanoate Chemical compound C([C@@H](C(=O)OC)N1C=CC=C1)C(C=C1)=CC=C1OCCN(CC1)CCN1C1=CC=CC=C1 ZHJVRXSCJHSGSY-VWLOTQADSA-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
- GQTXKEVAUZYHGE-UHFFFAOYSA-N methyl 2-phenylprop-2-enoate Chemical compound COC(=O)C(=C)C1=CC=CC=C1 GQTXKEVAUZYHGE-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- 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 2
- HUJCWGNXDRFPQZ-UHFFFAOYSA-N methyl 3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethylamino]phenyl]-2-pyrrol-1-ylpropanoate Chemical compound C1=CC=CN1C(C(=O)OC)CC(C=C1)=CC=C1NCCC(=C(O1)C)N=C1C1=CC=CC=C1 HUJCWGNXDRFPQZ-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 3
- 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 2
- 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 2
- NNCKMTGSQFYRCO-UHFFFAOYSA-N methyl 2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)-3-[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]phenyl]propanoate Chemical compound N1=C(C=2C=CC=CC=2)OC(C)=C1C(C(=O)OC)CC(C=C1)=CC=C1CCCC(=C(O1)C)N=C1C1=CC=CC=C1 NNCKMTGSQFYRCO-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 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 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- WASVXFPJDLYXSY-UHFFFAOYSA-N 2-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methylamino]-2-phenylacetic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CNC(C(O)=O)C1=CC=CC=C1 WASVXFPJDLYXSY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 claims 1
- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 claims 1
- 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 1
- 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 1
- JMNKVXIPKMARAJ-PMERELPUSA-N methyl (2s)-2-(2-benzoylpyrrol-1-yl)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoate Chemical compound C([C@@H](C(=O)OC)N1C(=CC=C1)C(=O)C=1C=CC=CC=1)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 JMNKVXIPKMARAJ-PMERELPUSA-N 0.000 claims 1
- BQJMTYVZAXYRHA-MHZLTWQESA-N methyl (2s)-2-(2-butanoylpyrrol-1-yl)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoate Chemical compound CCCC(=O)C1=CC=CN1[C@H](C(=O)OC)CC(C=C1)=CC=C1OCCC1=C(C)OC(C=2C=CC=CC=2)=N1 BQJMTYVZAXYRHA-MHZLTWQESA-N 0.000 claims 1
- UGEUADWKHJNFOR-DEOSSOPVSA-N methyl (2s)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-[2-(2,2,2-trifluoroacetyl)pyrrol-1-yl]propanoate Chemical compound C([C@@H](C(=O)OC)N1C(=CC=C1)C(=O)C(F)(F)F)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 UGEUADWKHJNFOR-DEOSSOPVSA-N 0.000 claims 1
- 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 1
- IEOWWQFTVVSQQN-YTTGMZPUSA-N methyl (2s)-3-[4-[[benzyl-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethyl]amino]methyl]phenyl]-2-pyrrol-1-ylpropanoate Chemical compound C([C@@H](C(=O)OC)N1C=CC=C1)C(C=C1)=CC=C1CN(CC=1C=CC=CC=1)CCC(=C(O1)C)N=C1C1=CC=CC=C1 IEOWWQFTVVSQQN-YTTGMZPUSA-N 0.000 claims 1
- KYMPDBIAIPVJMX-UHFFFAOYSA-N methyl 2-(3-bromopyrrol-1-yl)-2-methyl-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoate Chemical compound C1=CC(Br)=CN1C(C)(C(=O)OC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 KYMPDBIAIPVJMX-UHFFFAOYSA-N 0.000 claims 1
- CTUXXNKWTPOUDN-UHFFFAOYSA-N methyl 2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoate Chemical compound N1=C(C=2C=CC=CC=2)OC(C)=C1C(C(=O)OC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 CTUXXNKWTPOUDN-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 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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- 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
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- 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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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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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
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- 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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- 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
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- 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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- 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
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- 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
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Landscapes
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- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| PA8594401A1 (es) * | 2003-02-21 | 2004-09-16 | Pfizer | Acidos carboxilicos de heteroarilo condensado como agonista del ppar |
| EP1620088A4 (en) * | 2003-04-28 | 2007-08-29 | Bayer Pharmaceuticals Corp | ACETIC INDOLE ACID DERIVATIVES AND THEIR USE AS PHARMACEUTICAL AGENTS |
| WO2005000841A1 (en) * | 2003-06-27 | 2005-01-06 | Warner-Lambert Company Llc | Preparation of n2-alkylated 1,2,3-triazoles |
| BRPI0412236A (pt) * | 2003-07-02 | 2006-09-12 | Hoffmann La Roche | compostos, processo para a sua manufatura, composições farmacêuticas que compreendem os mesmos, método para o tratamento e/ou prevenção de enfermidades que são moduladas por agonistas ppar(delta) e/ou ppar(alfa), e utilização desses compostos |
| AU2004259738B2 (en) * | 2003-07-17 | 2011-11-17 | Plexxikon, Inc. | PPAR active compounds |
| CN100509802C (zh) * | 2003-11-05 | 2009-07-08 | 霍夫曼-拉罗奇有限公司 | 作为ppar激活剂的杂芳基衍生物 |
| CN1886133B (zh) | 2003-12-04 | 2010-12-01 | 财团法人卫生研究院 | 吲哚化合物 |
| ES2285554T3 (es) | 2003-12-11 | 2007-11-16 | GALDERMA RESEARCH & DEVELOPMENT | Nuevos compuestos que son moduladores de receptores de tipo ppar y su uso en composiciones cosmeticas o farmaceuticas. |
| 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 |
| WO2005063729A1 (en) | 2003-12-25 | 2005-07-14 | Takeda Pharmaceutical Company Limited | 3-(4-benzyloxyphenyl)propanoic acid derivatives |
| JP4599395B2 (ja) * | 2004-03-09 | 2010-12-15 | エフ.ホフマン−ラ ロシュ アーゲー | Ppar活性化剤としてのピラゾリルインドリル誘導体 |
| 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 |
| NZ572268A (en) * | 2006-04-18 | 2011-09-30 | Nippon Chemiphar Co | Activating agent for peroxisome proliferator activated receptor delta (ppar) |
| 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 |
| AU2013202514B2 (en) * | 2006-04-18 | 2015-09-17 | Nippon Chemiphar Co., Ltd. | Activating agent for peroxisome proliferator activated receptor delta |
| PT2277874T (pt) | 2008-04-15 | 2018-08-10 | Nippon Chemiphar Co | Ativador para recetor ativado por proliferador de peroxissoma |
| 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 |
| 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 |
| 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 |
| WO2025141118A1 (en) * | 2023-12-27 | 2025-07-03 | Institut National de la Santé et de la Recherche Médicale | Arylalkyloxyindole compounds and derivatives and their use |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69941777D1 (de) * | 1998-03-10 | 2010-01-21 | Ono Pharmaceutical Co | Carbonsäurederivate und medikamente die diese als aktiven wirkstoff enthalten |
| 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 |
| JP2002527507A (ja) * | 1998-10-21 | 2002-08-27 | ノボ ノルディスク アクティーゼルスカブ | 新規化合物類、それらの調製及び使用 |
| US6274608B1 (en) * | 1999-04-20 | 2001-08-14 | Novo Nordisk A/S | Compounds, their preparation and use |
| NZ515284A (en) * | 1999-04-28 | 2004-12-24 | Dr | Substituted bicyclic heterocycles, process for their preparation and their use as antiobesity and hypocholesterolemic agents |
| EP1210345B1 (en) * | 1999-09-08 | 2004-03-03 | Glaxo Group Limited | Oxazole ppar antagonists |
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2002
- 2002-07-15 EP EP05104581A patent/EP1577305A1/en not_active Withdrawn
- 2002-07-15 ES ES02745739T patent/ES2260456T3/es not_active Expired - Lifetime
- 2002-07-15 EP EP02745739A patent/EP1423363B1/en not_active Expired - Lifetime
- 2002-07-15 EA EA200400140A patent/EA200400140A1/ru unknown
- 2002-07-15 CA CA002458621A patent/CA2458621A1/en not_active Abandoned
- 2002-07-15 CN CNA028216350A patent/CN1558897A/zh active Pending
- 2002-07-15 JP JP2003523217A patent/JP2005504778A/ja not_active Withdrawn
- 2002-07-15 BR BR0212069-0A patent/BR0212069A/pt not_active IP Right Cessation
- 2002-07-15 OA OA1200400053A patent/OA12653A/en unknown
- 2002-07-15 SK SK118-2004A patent/SK1182004A3/sk not_active Application Discontinuation
- 2002-07-15 IL IL15988602A patent/IL159886A0/xx unknown
- 2002-07-15 PL PL02369569A patent/PL369569A1/xx not_active Application Discontinuation
- 2002-07-15 AT AT02745739T patent/ATE323674T1/de not_active IP Right Cessation
- 2002-07-15 HU HU0401620A patent/HUP0401620A2/hu unknown
- 2002-07-15 WO PCT/IB2002/002843 patent/WO2003018553A1/en not_active Ceased
- 2002-07-15 HR HR20040164A patent/HRP20040164A2/hr not_active Application Discontinuation
- 2002-07-15 DE DE60210784T patent/DE60210784T2/de not_active Expired - Fee Related
- 2002-07-15 MX MXPA04001968A patent/MXPA04001968A/es unknown
- 2002-07-15 KR KR10-2004-7003019A patent/KR20040044515A/ko not_active Ceased
- 2002-07-15 EE EEP200400075A patent/EE200400075A/xx unknown
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- 2002-08-27 UY UY27424A patent/UY27424A1/es not_active Application Discontinuation
- 2002-08-27 PA PA20028553701A patent/PA8553701A1/es unknown
- 2002-08-27 AR ARP020103209A patent/AR036301A1/es unknown
- 2002-08-28 SV SV2002001213A patent/SV2003001213A/es not_active Application Discontinuation
- 2002-08-28 GT GT200200175A patent/GT200200175A/es unknown
- 2002-08-29 AP APAP/P/2002/002616A patent/AP2002002616A0/en unknown
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2004
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- 2004-01-16 ZA ZA2004/00374A patent/ZA200400374B/en unknown
- 2004-02-19 MA MA27537A patent/MA27135A1/fr unknown
- 2004-02-24 BG BG108597A patent/BG108597A/bg unknown
- 2004-02-25 TN TNP2004000038A patent/TNSN04038A1/fr unknown
- 2004-02-27 NO NO20040881A patent/NO20040881L/no not_active Application Discontinuation
- 2004-03-03 EC EC2004004999A patent/ECSP044999A/es unknown
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