JP2017501174A5 - - Google Patents
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- JP2017501174A5 JP2017501174A5 JP2016540956A JP2016540956A JP2017501174A5 JP 2017501174 A5 JP2017501174 A5 JP 2017501174A5 JP 2016540956 A JP2016540956 A JP 2016540956A JP 2016540956 A JP2016540956 A JP 2016540956A JP 2017501174 A5 JP2017501174 A5 JP 2017501174A5
- Authority
- JP
- Japan
- Prior art keywords
- oxazol
- chloro
- propanoic acid
- oxobenzo
- ethoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 9
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- -1 5-chloro-2-oxobenzo [d] oxazol-3 (2H) -yl Chemical group 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 3
- QPMPFAMMRAXUAV-UHFFFAOYSA-N 3-(5-chloro-6-methyl-2-oxo-1,3-benzoxazol-3-yl)propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)C QPMPFAMMRAXUAV-UHFFFAOYSA-N 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims 3
- NHCIPHVVYOECGF-JHJMLUEUSA-N (2R)-3-[5-chloro-6-[1-(5-methylpyridin-2-yl)ethoxy]-2-oxo-1,3-benzoxazol-3-yl]-2-methylpropanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)C[C@H](C(=O)O)C)C1)OC(C)C1=NC=C(C=C1)C NHCIPHVVYOECGF-JHJMLUEUSA-N 0.000 claims 2
- NHCIPHVVYOECGF-PXYINDEMSA-N (2S)-3-[5-chloro-6-[1-(5-methylpyridin-2-yl)ethoxy]-2-oxo-1,3-benzoxazol-3-yl]-2-methylpropanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)C[C@@H](C(=O)O)C)C1)OC(C)C1=NC=C(C=C1)C NHCIPHVVYOECGF-PXYINDEMSA-N 0.000 claims 2
- ODWSXTKSQNMMMQ-UHFFFAOYSA-N 3-(5-chloro-2-oxo-1,3-benzoxazol-3-yl)propanoic acid Chemical compound ClC1=CC=C2OC(=O)N(CCC(=O)O)C2=C1 ODWSXTKSQNMMMQ-UHFFFAOYSA-N 0.000 claims 2
- PVGOQRJICUIPTG-SNVBAGLBSA-N 3-[5-chloro-2-oxo-6-[(1R)-1-pyridin-2-ylethoxy]-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)O[C@H](C)C1=NC=CC=C1 PVGOQRJICUIPTG-SNVBAGLBSA-N 0.000 claims 2
- 206010051379 Systemic Inflammatory Response Syndrome Diseases 0.000 claims 2
- 230000001154 acute effect Effects 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 2
- 235000019260 propionic acid Nutrition 0.000 claims 2
- WSGJLXFMKJGHCQ-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;propanoic acid Chemical compound CCC(O)=O.OCC(N)(CO)CO WSGJLXFMKJGHCQ-UHFFFAOYSA-N 0.000 claims 1
- MIGAKMWKMLYGJX-UHFFFAOYSA-N 3-(5,6-dichloro-2-oxo-1,3-benzoxazol-3-yl)propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)Cl MIGAKMWKMLYGJX-UHFFFAOYSA-N 0.000 claims 1
- GTJRCPBOWQKMQU-UHFFFAOYSA-N 3-(5-chloro-2-oxo-6-phenylmethoxy-1,3-benzoxazol-3-yl)propanoic acid Chemical compound C(C1=CC=CC=C1)OC1=CC2=C(N(C(O2)=O)CCC(=O)O)C=C1Cl GTJRCPBOWQKMQU-UHFFFAOYSA-N 0.000 claims 1
- GDPGLNQAEBZRGB-UHFFFAOYSA-N 3-(5-chloro-2-oxo-6-propan-2-yloxy-1,3-benzoxazol-3-yl)propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)OC(C)C GDPGLNQAEBZRGB-UHFFFAOYSA-N 0.000 claims 1
- GOSORROHNFUEQN-UHFFFAOYSA-N 3-(5-chloro-2-oxo-6-propoxy-1,3-benzoxazol-3-yl)propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)OCCC GOSORROHNFUEQN-UHFFFAOYSA-N 0.000 claims 1
- LEJTWJZGMMVIOQ-UHFFFAOYSA-N 3-(5-chloro-6-cyano-2-oxo-1,3-benzoxazol-3-yl)propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)C#N LEJTWJZGMMVIOQ-UHFFFAOYSA-N 0.000 claims 1
- HKSMABARBFQPBS-UHFFFAOYSA-N 3-(5-chloro-6-cyclobutyloxy-2-oxo-1,3-benzoxazol-3-yl)propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)OC1CCC1 HKSMABARBFQPBS-UHFFFAOYSA-N 0.000 claims 1
- AYXQPTCYJAJHBG-UHFFFAOYSA-N 3-(5-chloro-6-cyclopropyloxy-2-oxo-1,3-benzoxazol-3-yl)propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)OC1CC1 AYXQPTCYJAJHBG-UHFFFAOYSA-N 0.000 claims 1
- KPOKXAQERBEAHE-UHFFFAOYSA-N 3-(5-chloro-6-ethoxy-2-oxo-1,3-benzoxazol-3-yl)propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)OCC KPOKXAQERBEAHE-UHFFFAOYSA-N 0.000 claims 1
- ZHMLSGOGTNVURP-UHFFFAOYSA-N 3-(5-chloro-6-ethyl-2-oxo-1,3-benzoxazol-3-yl)propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)CC ZHMLSGOGTNVURP-UHFFFAOYSA-N 0.000 claims 1
- HOFDARMYNOYQIW-UHFFFAOYSA-N 3-(5-chloro-6-fluoro-2-oxo-1,3-benzoxazol-3-yl)propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)F HOFDARMYNOYQIW-UHFFFAOYSA-N 0.000 claims 1
- ULGMFNQVPOXZSJ-UHFFFAOYSA-N 3-(5-chloro-6-methoxy-2-oxo-1,3-benzoxazol-3-yl)propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)OC ULGMFNQVPOXZSJ-UHFFFAOYSA-N 0.000 claims 1
- PJFPMJFITAPUHB-UHFFFAOYSA-N 3-(6-bromo-5-chloro-2-oxo-1,3-benzoxazol-3-yl)propanoic acid Chemical compound BrC1=CC2=C(N(C(O2)=O)CCC(=O)O)C=C1Cl PJFPMJFITAPUHB-UHFFFAOYSA-N 0.000 claims 1
- PVGOQRJICUIPTG-UHFFFAOYSA-N 3-[5-chloro-2-oxo-6-(1-pyridin-2-ylethoxy)-1,3-benzoxazol-3-yl]propanoic acid Chemical compound C=1C=2OC(=O)N(CCC(O)=O)C=2C=C(Cl)C=1OC(C)C1=CC=CC=N1 PVGOQRJICUIPTG-UHFFFAOYSA-N 0.000 claims 1
- LEGCGTRFFZCTEQ-UHFFFAOYSA-N 3-[5-chloro-2-oxo-6-(1-pyrimidin-2-ylethoxy)-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)OC(C)C1=NC=CC=N1 LEGCGTRFFZCTEQ-UHFFFAOYSA-N 0.000 claims 1
- ULNMFTNEJCPEQH-UHFFFAOYSA-N 3-[5-chloro-2-oxo-6-(2,2,2-trifluoroethoxy)-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)OCC(F)(F)F ULNMFTNEJCPEQH-UHFFFAOYSA-N 0.000 claims 1
- GVDOFIUAXZUKHH-UHFFFAOYSA-N 3-[5-chloro-2-oxo-6-(3,3,3-trifluoropropoxy)-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)OCCC(F)(F)F GVDOFIUAXZUKHH-UHFFFAOYSA-N 0.000 claims 1
- MOQVGEWGYXWBBJ-UHFFFAOYSA-N 3-[5-chloro-2-oxo-6-(pyridazin-3-ylmethoxy)-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)OCC=1N=NC=CC1 MOQVGEWGYXWBBJ-UHFFFAOYSA-N 0.000 claims 1
- VIXQYKRJXFZDNN-UHFFFAOYSA-N 3-[5-chloro-2-oxo-6-(pyridin-2-ylmethoxy)-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)OCC1=NC=CC=C1 VIXQYKRJXFZDNN-UHFFFAOYSA-N 0.000 claims 1
- KQASKXOQZUOUPF-UHFFFAOYSA-N 3-[5-chloro-2-oxo-6-(pyrimidin-2-ylmethoxy)-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)OCC1=NC=CC=N1 KQASKXOQZUOUPF-UHFFFAOYSA-N 0.000 claims 1
- NEIWTLNQTVXJFF-SECBINFHSA-N 3-[5-chloro-2-oxo-6-[(1R)-1-pyridazin-3-ylethoxy]-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)O[C@H](C)C=1N=NC=CC1 NEIWTLNQTVXJFF-SECBINFHSA-N 0.000 claims 1
- OHNCPBZDEWTOQI-CQSZACIVSA-N 3-[5-chloro-2-oxo-6-[(1R)-1-pyridin-2-ylpropoxy]-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)O[C@H](CC)C1=NC=CC=C1 OHNCPBZDEWTOQI-CQSZACIVSA-N 0.000 claims 1
- NEIWTLNQTVXJFF-VIFPVBQESA-N 3-[5-chloro-2-oxo-6-[(1S)-1-pyridazin-3-ylethoxy]-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)O[C@@H](C)C=1N=NC=CC1 NEIWTLNQTVXJFF-VIFPVBQESA-N 0.000 claims 1
- PVGOQRJICUIPTG-JTQLQIEISA-N 3-[5-chloro-2-oxo-6-[(1S)-1-pyridin-2-ylethoxy]-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)O[C@@H](C)C1=NC=CC=C1 PVGOQRJICUIPTG-JTQLQIEISA-N 0.000 claims 1
- CGBDDTMTJSBJRF-UHFFFAOYSA-N 3-[5-chloro-6-(1-methoxypropan-2-yloxy)-2-oxo-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)OC(COC)C CGBDDTMTJSBJRF-UHFFFAOYSA-N 0.000 claims 1
- KNFPPVGKNXFCPJ-UHFFFAOYSA-N 3-[5-chloro-6-(1H-imidazol-2-ylmethoxy)-2-oxo-1,3-benzoxazol-3-yl]propanoic acid Chemical compound N1C(=NC=C1)COC1=CC2=C(N(C(O2)=O)CCC(=O)O)C=C1Cl KNFPPVGKNXFCPJ-UHFFFAOYSA-N 0.000 claims 1
- JKHHENDLKYIXQJ-UHFFFAOYSA-N 3-[5-chloro-6-(2-methoxyethoxy)-2-oxo-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)OCCOC JKHHENDLKYIXQJ-UHFFFAOYSA-N 0.000 claims 1
- ZVIIDZJVPGJYEL-UHFFFAOYSA-N 3-[5-chloro-6-(2-methylpropoxy)-2-oxo-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)OCC(C)C ZVIIDZJVPGJYEL-UHFFFAOYSA-N 0.000 claims 1
- OGZMEMUZINOQKM-UHFFFAOYSA-N 3-[5-chloro-6-(2-methylpropyl)-2-oxo-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)CC(C)C OGZMEMUZINOQKM-UHFFFAOYSA-N 0.000 claims 1
- VZSAISDQEBTHJE-UHFFFAOYSA-N 3-[5-chloro-6-(cyclobutylmethoxy)-2-oxo-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)OCC1CCC1 VZSAISDQEBTHJE-UHFFFAOYSA-N 0.000 claims 1
- HRLUJVVPOYIXCE-UHFFFAOYSA-N 3-[5-chloro-6-(cyclopropylmethoxy)-2-oxo-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)OCC1CC1 HRLUJVVPOYIXCE-UHFFFAOYSA-N 0.000 claims 1
- SMEUJSDVNBGJTB-UHFFFAOYSA-N 3-[5-chloro-6-(oxetan-3-ylmethoxy)-2-oxo-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)OCC1COC1 SMEUJSDVNBGJTB-UHFFFAOYSA-N 0.000 claims 1
- ILHZCBQKNBPRKK-UHFFFAOYSA-N 3-[5-chloro-6-(oxetan-3-yloxy)-2-oxo-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)OC1COC1 ILHZCBQKNBPRKK-UHFFFAOYSA-N 0.000 claims 1
- CBHVUTHBEDBHJJ-UHFFFAOYSA-N 3-[5-chloro-6-[(1-methylimidazol-2-yl)methoxy]-2-oxo-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)OCC=1N(C=CN1)C CBHVUTHBEDBHJJ-UHFFFAOYSA-N 0.000 claims 1
- DVJIQSJUTRTQEY-LLVKDONJSA-N 3-[5-chloro-6-[(1R)-1-(4-methylpyridin-2-yl)ethoxy]-2-oxo-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)O[C@H](C)C1=NC=CC(=C1)C DVJIQSJUTRTQEY-LLVKDONJSA-N 0.000 claims 1
- KLSVQSBBWJOTAB-SECBINFHSA-N 3-[5-chloro-6-[(1R)-1-(5-chloropyridin-2-yl)ethoxy]-2-oxo-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)O[C@H](C)C1=NC=C(C=C1)Cl KLSVQSBBWJOTAB-SECBINFHSA-N 0.000 claims 1
- XRWTZEXUDFQKOZ-SECBINFHSA-N 3-[5-chloro-6-[(1R)-1-(5-fluoropyridin-2-yl)ethoxy]-2-oxo-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)O[C@H](C)C1=NC=C(C=C1)F XRWTZEXUDFQKOZ-SECBINFHSA-N 0.000 claims 1
- PJHHNILPPKWMGT-LLVKDONJSA-N 3-[5-chloro-6-[(1R)-1-(5-methylpyridin-2-yl)ethoxy]-2-oxo-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)O[C@H](C)C1=NC=C(C=C1)C PJHHNILPPKWMGT-LLVKDONJSA-N 0.000 claims 1
- WGPMVXCSHVIAAV-OAHLLOKOSA-N 3-[5-chloro-6-[(1R)-1-(5-methylpyridin-2-yl)propoxy]-2-oxo-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)O[C@H](CC)C1=NC=C(C=C1)C WGPMVXCSHVIAAV-OAHLLOKOSA-N 0.000 claims 1
- NGFOKSNTKAZYEB-SNVBAGLBSA-N 3-[5-chloro-6-[(1R)-1-(6-methylpyridazin-3-yl)ethoxy]-2-oxo-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)O[C@H](C)C=1N=NC(=CC1)C NGFOKSNTKAZYEB-SNVBAGLBSA-N 0.000 claims 1
- UPKBFTHCVKDUPD-LLVKDONJSA-N 3-[5-chloro-6-[(1R)-1-(6-methylpyridin-2-yl)ethoxy]-2-oxo-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)O[C@H](C)C1=NC(=CC=C1)C UPKBFTHCVKDUPD-LLVKDONJSA-N 0.000 claims 1
- YNMJGONRZKCIGL-QMMMGPOBSA-N 3-[5-chloro-6-[(1S)-1-(1,3-oxazol-2-yl)ethoxy]-2-oxo-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)O[C@@H](C)C=1OC=CN1 YNMJGONRZKCIGL-QMMMGPOBSA-N 0.000 claims 1
- NGFOKSNTKAZYEB-JTQLQIEISA-N 3-[5-chloro-6-[(1S)-1-(6-methylpyridazin-3-yl)ethoxy]-2-oxo-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)O[C@@H](C)C=1N=NC(=CC1)C NGFOKSNTKAZYEB-JTQLQIEISA-N 0.000 claims 1
- NIOBGDAGNQWJON-UHFFFAOYSA-N 3-[5-chloro-6-[(2-methyl-1,3-oxazol-5-yl)methoxy]-2-oxo-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)OCC1=CN=C(O1)C NIOBGDAGNQWJON-UHFFFAOYSA-N 0.000 claims 1
- AQRWVYDBYNMRNQ-UHFFFAOYSA-N 3-[5-chloro-6-[(2-methylpyridin-3-yl)methoxy]-2-oxo-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)OCC=1C(=NC=CC1)C AQRWVYDBYNMRNQ-UHFFFAOYSA-N 0.000 claims 1
- HOMLHTCVJYGVBE-UHFFFAOYSA-N 3-[5-chloro-6-[(2-methylpyridin-4-yl)methoxy]-2-oxo-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)OCC1=CC(=NC=C1)C HOMLHTCVJYGVBE-UHFFFAOYSA-N 0.000 claims 1
- LDEZRVLKWVZQOR-UHFFFAOYSA-N 3-[5-chloro-6-[(5-chloropyridin-2-yl)methoxy]-2-oxo-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)OCC1=NC=C(C=C1)Cl LDEZRVLKWVZQOR-UHFFFAOYSA-N 0.000 claims 1
- FMXFYXGRASQAQU-UHFFFAOYSA-N 3-[5-chloro-6-[(5-fluoropyridin-2-yl)methoxy]-2-oxo-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)OCC1=NC=C(C=C1)F FMXFYXGRASQAQU-UHFFFAOYSA-N 0.000 claims 1
- DGUZBUHMURJOLJ-UHFFFAOYSA-N 3-[5-chloro-6-[(5-methyl-1,3-oxazol-2-yl)methoxy]-2-oxo-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)OCC=1OC(=CN1)C DGUZBUHMURJOLJ-UHFFFAOYSA-N 0.000 claims 1
- MDYORKPRKZMDLE-UHFFFAOYSA-N 3-[5-chloro-6-[(5-methylpyridin-2-yl)methoxy]-2-oxo-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)OCC1=NC=C(C=C1)C MDYORKPRKZMDLE-UHFFFAOYSA-N 0.000 claims 1
- NZOJDAVPZLTEHR-UHFFFAOYSA-N 3-[5-chloro-6-[(6-methylpyridazin-3-yl)methoxy]-2-oxo-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)OCC=1N=NC(=CC1)C NZOJDAVPZLTEHR-UHFFFAOYSA-N 0.000 claims 1
- ONUJCJYLICOYKC-UHFFFAOYSA-N 3-[5-chloro-6-[(6-methylpyridin-3-yl)methoxy]-2-oxo-1,3-benzoxazol-3-yl]propanoic acid Chemical compound ClC=1C(=CC2=C(N(C(O2)=O)CCC(=O)O)C1)OCC=1C=NC(=CC1)C ONUJCJYLICOYKC-UHFFFAOYSA-N 0.000 claims 1
- 206010065040 AIDS dementia complex Diseases 0.000 claims 1
- 208000000197 Acute Cholecystitis Diseases 0.000 claims 1
- 208000009304 Acute Kidney Injury Diseases 0.000 claims 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 102000014461 Ataxins Human genes 0.000 claims 1
- 108010078286 Ataxins Proteins 0.000 claims 1
- 206010008025 Cerebellar ataxia Diseases 0.000 claims 1
- 206010008614 Cholecystitis acute Diseases 0.000 claims 1
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- 206010022680 Intestinal ischaemia Diseases 0.000 claims 1
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| NZ732002A (en) * | 2014-12-19 | 2023-07-28 | Univ Court Univ Of Edinburgh | 3-(6-alkoxy-5-chlorobenzo[d]isoxazol-3-yl)propanoic acid useful as kynurenine monooxygenase inhibitors |
| GB201508857D0 (en) | 2015-05-22 | 2015-07-01 | Glaxosmithkline Ip Dev Ltd | Compounds |
| GB201508864D0 (en) | 2015-05-22 | 2015-07-01 | Glaxosmithkline Ip Dev Ltd | Compounds |
| CN106810463A (zh) * | 2016-12-29 | 2017-06-09 | 沈阳绿洲制药有限责任公司 | 一种盐酸奥布卡因的制备方法 |
| GB2568549A (en) * | 2017-11-21 | 2019-05-22 | Univ Leicester | New compounds and uses |
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| JPS5498330A (en) * | 1978-01-17 | 1979-08-03 | Nippon Nohyaku Co Ltd | Agricultural and horticultural fungicide |
| JPS55167282A (en) * | 1979-06-12 | 1980-12-26 | Fujisawa Pharmaceut Co Ltd | Piperazine derivative or its salt and its preparation |
| JPS5697268A (en) * | 1979-12-28 | 1981-08-05 | Fujisawa Pharmaceut Co Ltd | Lower alkanoic acid derivative, salt and preparation thereof and preventing agent and remedy for diabetic complication containing the same as active constituent |
| JPS5798330A (en) * | 1980-12-12 | 1982-06-18 | Matsuda Seisakusho:Kk | Plastic material injection apparatus |
| SU1143745A1 (ru) * | 1983-11-23 | 1985-03-07 | Каунасский Политехнический Институт Им.Антанаса Снечкуса | Способ получени производных 3-(3-бензоксазолонил)пропановой кислоты |
| AU2001262711A1 (en) * | 2000-06-08 | 2001-12-17 | Mitsubishi Pharma Corporation | Cytoprotectors |
| EP1424333A1 (en) | 2002-11-28 | 2004-06-02 | Newron Pharmaceuticals S.p.A. | Halothenoyl-cyclopropane-1-carboxylic acid derivatives |
| EP1475385A1 (en) | 2003-05-05 | 2004-11-10 | Newron Pharmaceuticals S.p.A. | Glycoside derivatives of 2-(3,4-dichlorobenzoyl)-cycopropane-1-carboxylic acid |
| BRPI0607469A2 (pt) * | 2005-02-22 | 2009-09-08 | Ranbaxy Lab Ltd | derivados de ácido 5-fenil-pentanóico, seus processos de preparação, composição farmacêutica compreendendo os mesmos e processo de separação dos referidos derivados |
| US8071631B2 (en) | 2006-08-16 | 2011-12-06 | The J. David Gladstone Institutes, A Testamentary Trust Established Under The Will Of J. David Gladstone | Small molecule inhibitors of kynurenine-3-monooxygenase |
| EP2054397B1 (en) | 2006-08-16 | 2015-10-07 | The J. David Gladstone Institutes, A Testamentary Trust Established under The Will of J. David Gladstone | Small molecule inhibitors of kynurenine-3-monooxygenase |
| US20110230428A1 (en) | 2008-07-22 | 2011-09-22 | John Wityak | Certain kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| US8691824B2 (en) | 2008-08-04 | 2014-04-08 | Chdi Foundation, Inc. | Certain kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| AU2009279787B2 (en) | 2008-08-04 | 2014-05-29 | Chdi Foundation, Inc. | Certain kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| NZ601547A (en) | 2010-01-25 | 2014-04-30 | Chdi Foundation Inc | Certain kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| JP5498330B2 (ja) * | 2010-09-17 | 2014-05-21 | 積水化学工業株式会社 | 建築用パネルの輸送用支持材及び建築用パネル |
| EA201490163A1 (ru) | 2011-07-28 | 2014-06-30 | Схди Фаундейшн, Инк. | Ингибиторы кинуренин-3-монооксигеназы, фармацевтические композиции и способы их применения |
| PH12017502049A1 (en) * | 2011-08-30 | 2018-08-29 | Chdi Foundation Inc | Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| EP3130583B1 (en) * | 2012-04-05 | 2024-01-03 | CHDI Foundation, Inc. | Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
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