CA2523714A1 - Substituted carboxylic acids - Google Patents
Substituted carboxylic acids Download PDFInfo
- Publication number
- CA2523714A1 CA2523714A1 CA002523714A CA2523714A CA2523714A1 CA 2523714 A1 CA2523714 A1 CA 2523714A1 CA 002523714 A CA002523714 A CA 002523714A CA 2523714 A CA2523714 A CA 2523714A CA 2523714 A1 CA2523714 A1 CA 2523714A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- phenyl
- biphenyl
- benzyl
- benzofuran
- 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.)
- Abandoned
Links
- 150000001735 carboxylic acids Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 354
- 238000000034 method Methods 0.000 claims abstract description 86
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 20
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 250
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 240
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 187
- 229910052736 halogen Inorganic materials 0.000 claims description 162
- 150000002367 halogens Chemical class 0.000 claims description 162
- -1 phenyl (C1-C4) alkyl Chemical group 0.000 claims description 128
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 78
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 69
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 68
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 64
- 125000000217 alkyl group Chemical group 0.000 claims description 60
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 60
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 52
- 125000001188 haloalkyl group Chemical group 0.000 claims description 46
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 41
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 39
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 39
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 38
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 37
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 28
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 27
- 125000001041 indolyl group Chemical group 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 21
- 125000002252 acyl group Chemical group 0.000 claims description 21
- 125000004122 cyclic group Chemical group 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000003386 piperidinyl group Chemical group 0.000 claims description 17
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims description 17
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 16
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 15
- 125000005545 phthalimidyl group Chemical group 0.000 claims description 15
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 15
- 125000002757 morpholinyl group Chemical group 0.000 claims description 14
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 13
- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 11
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 9
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 9
- 239000002671 adjuvant Substances 0.000 claims description 8
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 8
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- FOUKSPNWVQXNSE-UHFFFAOYSA-N 4-[4-(4-dibenzofuran-4-ylphenyl)phenyl]-4-oxo-2-[[3-(trifluoromethyl)phenyl]methyl]butanoic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C3=C(C4=CC=CC=C4O3)C=CC=2)C=CC=1C(=O)CC(C(=O)O)CC1=CC=CC(C(F)(F)F)=C1 FOUKSPNWVQXNSE-UHFFFAOYSA-N 0.000 claims description 5
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 5
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 5
- 229960005190 phenylalanine Drugs 0.000 claims description 5
- NQDPPXMOGTWHAA-UHFFFAOYSA-N 2-benzyl-4-[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenyl]-4-oxobutanoic acid Chemical compound C=1C=CC=CC=1CC(C(=O)O)CC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1C(C1=CC=CC=C1O1)=C1CC1=CC=CC=C1 NQDPPXMOGTWHAA-UHFFFAOYSA-N 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- LSKFWNSFOPZXKV-UHFFFAOYSA-N methyl 4-[4-(4-dibenzofuran-4-ylphenyl)phenyl]-4-oxo-2-[[3-(trifluoromethyl)phenyl]methyl]butanoate Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=CC=1C(=O)CC(C(=O)OC)CC1=CC=CC(C(F)(F)F)=C1 LSKFWNSFOPZXKV-UHFFFAOYSA-N 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- BCAPAVNRPJLWBU-UHFFFAOYSA-N 2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenyl]sulfonylamino]butanoic acid Chemical compound C1=CC(S(=O)(=O)NC(CC)C(O)=O)=CC=C1C1=CC=C(C=2C3=CC=CC=C3OC=2CC=2C=CC=CC=2)C=C1 BCAPAVNRPJLWBU-UHFFFAOYSA-N 0.000 claims description 3
- WAKZELVPMHJKIX-UHFFFAOYSA-N 2-benzyl-4-[2-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenyl]-4-oxobutanoic acid Chemical compound C=1C=CC=CC=1CC(C(=O)O)CC(=O)C1=CC=CC=C1C(C=C1)=CC=C1C(C1=CC=CC=C1O1)=C1CC1=CC=CC=C1 WAKZELVPMHJKIX-UHFFFAOYSA-N 0.000 claims description 3
- VCOJXFLHAWTRFN-UHFFFAOYSA-N 2-benzyl-4-[3-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenyl]-4-oxobutanoic acid Chemical compound C=1C=CC=CC=1CC(C(=O)O)CC(=O)C(C=1)=CC=CC=1C(C=C1)=CC=C1C(C1=CC=CC=C1O1)=C1CC1=CC=CC=C1 VCOJXFLHAWTRFN-UHFFFAOYSA-N 0.000 claims description 3
- MPXRREHOMCUVNZ-UHFFFAOYSA-N 2-benzyl-4-[4-(4-indol-1-ylphenyl)phenyl]-4-oxobutanoic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C=C2)C=CC=1C(=O)CC(C(=O)O)CC1=CC=CC=C1 MPXRREHOMCUVNZ-UHFFFAOYSA-N 0.000 claims description 3
- WLXCNKISKIXXST-UHFFFAOYSA-N 2-benzyl-4-[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]-2,6-dimethylphenyl]-4-oxobutanoic acid Chemical compound CC1=CC(C=2C=CC(=CC=2)C=2C3=CC=CC=C3OC=2CC=2C=CC=CC=2)=CC(C)=C1C(=O)CC(C(O)=O)CC1=CC=CC=C1 WLXCNKISKIXXST-UHFFFAOYSA-N 0.000 claims description 3
- JZUWBNLKHMQGNS-UHFFFAOYSA-N 4-[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenyl]-2-[(4-methylsulfonylphenyl)methyl]-4-oxobutanoic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CC(C(O)=O)CC(=O)C1=CC=C(C=2C=CC(=CC=2)C=2C3=CC=CC=C3OC=2CC=2C=CC=CC=2)C=C1 JZUWBNLKHMQGNS-UHFFFAOYSA-N 0.000 claims description 3
- QNYLAIBEHNOPPA-UHFFFAOYSA-N 4-[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenyl]-2-[2-(1,3-dioxoisoindol-2-yl)ethyl]-4-oxobutanoic acid Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCC(C(=O)O)CC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1C(C1=CC=CC=C1O1)=C1CC1=CC=CC=C1 QNYLAIBEHNOPPA-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 3
- RVJUPLWFUPACJL-JGCGQSQUSA-N (2r)-2-[4-[4-(1-butylindolizin-2-yl)phenyl]phenoxy]-3-phenylpropanoic acid Chemical compound C([C@@H](OC1=CC=C(C=C1)C1=CC=C(C=C1)C=1C(=C2C=CC=CN2C=1)CCCC)C(O)=O)C1=CC=CC=C1 RVJUPLWFUPACJL-JGCGQSQUSA-N 0.000 claims description 2
- ALOFTPNNFBMPOW-MGBGTMOVSA-N (2r)-2-[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]-n-methyl-2-nitroanilino]-3-phenylpropanoic acid Chemical compound C([C@@H](N(C)C=1C(=CC(=CC=1)C=1C=CC(=CC=1)C=1C2=CC=CC=C2OC=1CC=1C=CC=CC=1)[N+]([O-])=O)C(O)=O)C1=CC=CC=C1 ALOFTPNNFBMPOW-MGBGTMOVSA-N 0.000 claims description 2
- QXMNORFCWALUQG-XIFFEERXSA-N (2s)-2-[4-[4-(1-butylindolizin-2-yl)phenyl]phenoxy]-4-phenylbutanoic acid Chemical compound C([C@H](OC1=CC=C(C=C1)C1=CC=C(C=C1)C=1C(=C2C=CC=CN2C=1)CCCC)C(O)=O)CC1=CC=CC=C1 QXMNORFCWALUQG-XIFFEERXSA-N 0.000 claims description 2
- LBHTUNQLUBVJPB-KDXMTYKHSA-N (2s)-2-[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]-2-[(2-phenylacetyl)amino]anilino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1C(=CC(=CC=1)C=1C=CC(=CC=1)C=1C2=CC=CC=C2OC=1CC=1C=CC=CC=1)NC(=O)CC=1C=CC=CC=1)C1=CC=CC=C1 LBHTUNQLUBVJPB-KDXMTYKHSA-N 0.000 claims description 2
- TVGXOXUAFKXOQE-VWLOTQADSA-N (2s)-2-[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]-2-nitroanilino]-3-hydroxypropanoic acid Chemical compound C1=C([N+]([O-])=O)C(N[C@@H](CO)C(O)=O)=CC=C1C1=CC=C(C=2C3=CC=CC=C3OC=2CC=2C=CC=CC=2)C=C1 TVGXOXUAFKXOQE-VWLOTQADSA-N 0.000 claims description 2
- VZQPGBMZSRZGNS-HKBQPEDESA-N (2s)-2-[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]-2-nitroanilino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1C(=CC(=CC=1)C=1C=CC(=CC=1)C=1C2=CC=CC=C2OC=1CC=1C=CC=CC=1)[N+]([O-])=O)C1=CC=CC=C1 VZQPGBMZSRZGNS-HKBQPEDESA-N 0.000 claims description 2
- PLDAFOFKTYIKNJ-MHZLTWQESA-N (2s)-2-[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]-2-nitroanilino]-4-methylsulfanylbutanoic acid Chemical compound C1=C([N+]([O-])=O)C(N[C@@H](CCSC)C(O)=O)=CC=C1C1=CC=C(C=2C3=CC=CC=C3OC=2CC=2C=CC=CC=2)C=C1 PLDAFOFKTYIKNJ-MHZLTWQESA-N 0.000 claims description 2
- QENAYTQFCPCMNZ-IBGZPJMESA-N (2s)-2-[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]-2-nitroanilino]propanoic acid Chemical compound C1=C([N+]([O-])=O)C(N[C@@H](C)C(O)=O)=CC=C1C1=CC=C(C=2C3=CC=CC=C3OC=2CC=2C=CC=CC=2)C=C1 QENAYTQFCPCMNZ-IBGZPJMESA-N 0.000 claims description 2
- CTHQHLFBRGKYCW-PMERELPUSA-N (2s)-2-[4-[4-(2-benzyl-4-fluoro-1-benzofuran-3-yl)phenyl]-2-nitroanilino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1C(=CC(=CC=1)C=1C=CC(=CC=1)C=1C2=C(F)C=CC=C2OC=1CC=1C=CC=CC=1)[N+]([O-])=O)C1=CC=CC=C1 CTHQHLFBRGKYCW-PMERELPUSA-N 0.000 claims description 2
- JIZSLXVSDDGOQR-DHUJRADRSA-N (2s)-2-[4-[4-[(2-benzyl-7-ethoxy-1-benzofuran-4-yl)methyl]phenyl]-2-nitroanilino]-3-phenylpropanoic acid Chemical compound C([C@H](NC1=CC=C(C=C1[N+]([O-])=O)C1=CC=C(C=C1)CC1=CC=C(C=2OC(CC=3C=CC=CC=3)=CC=21)OCC)C(O)=O)C1=CC=CC=C1 JIZSLXVSDDGOQR-DHUJRADRSA-N 0.000 claims description 2
- SKVKSLAIKOIQDV-HKBQPEDESA-N (2s)-2-[[4-[4-(1-butylindolizin-2-yl)phenyl]benzoyl]amino]-3-phenylpropanoic acid Chemical compound C([C@H](NC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)C=1C(=C2C=CC=CN2C=1)CCCC)C(O)=O)C1=CC=CC=C1 SKVKSLAIKOIQDV-HKBQPEDESA-N 0.000 claims description 2
- YAMKTWOCIRVYGC-HKBQPEDESA-N (2s)-2-[[4-[4-(1-butylindolizin-2-yl)phenyl]phenyl]sulfonylamino]-3-phenylpropanoic acid Chemical compound C([C@H](NS(=O)(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)C=1C(=C2C=CC=CN2C=1)CCCC)C(O)=O)C1=CC=CC=C1 YAMKTWOCIRVYGC-HKBQPEDESA-N 0.000 claims description 2
- JBPANPVYVLBQAD-YTTGMZPUSA-N (2s)-2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]-2-fluorophenyl]sulfonyl-methylamino]-3-phenylpropanoic acid Chemical compound C([C@H](N(C)S(=O)(=O)C=1C(=CC(=CC=1)C=1C=CC(=CC=1)C=1C2=CC=CC=C2OC=1CC=1C=CC=CC=1)F)C(O)=O)C1=CC=CC=C1 JBPANPVYVLBQAD-YTTGMZPUSA-N 0.000 claims description 2
- LJPVNLNUYKHZES-HKBQPEDESA-N (2s)-2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]-2-fluorophenyl]sulfonylamino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NS(=O)(=O)C=1C(=CC(=CC=1)C=1C=CC(=CC=1)C=1C2=CC=CC=C2OC=1CC=1C=CC=CC=1)F)C1=CC=CC=C1 LJPVNLNUYKHZES-HKBQPEDESA-N 0.000 claims description 2
- YTZDCEHZTQGKTO-YTTGMZPUSA-N (2s)-2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]benzoyl]-methylamino]-3-methylbutanoic acid Chemical compound C1=CC(C(=O)N(C)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=C(C=2C3=CC=CC=C3OC=2CC=2C=CC=CC=2)C=C1 YTZDCEHZTQGKTO-YTTGMZPUSA-N 0.000 claims description 2
- QEYCNFONUGAJSK-XIFFEERXSA-N (2s)-2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]benzoyl]-methylamino]-3-phenylpropanoic acid Chemical compound C([C@H](N(C)C(=O)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1C2=CC=CC=C2OC=1CC=1C=CC=CC=1)C(O)=O)C1=CC=CC=C1 QEYCNFONUGAJSK-XIFFEERXSA-N 0.000 claims description 2
- DBWYMVBSMCVXFS-YTTGMZPUSA-N (2s)-2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]benzoyl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1C2=CC=CC=C2OC=1CC=1C=CC=CC=1)C1=CC=CC=C1 DBWYMVBSMCVXFS-YTTGMZPUSA-N 0.000 claims description 2
- FCMQUHSEXDYETR-BHVANESWSA-N (2s)-2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenyl]sulfonyl-[[3-(trifluoromethyl)phenyl]methyl]amino]-4-methylpentanoic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C3=CC=CC=C3OC=2CC=2C=CC=CC=2)C=CC=1S(=O)(=O)N([C@@H](CC(C)C)C(O)=O)CC1=CC=CC(C(F)(F)F)=C1 FCMQUHSEXDYETR-BHVANESWSA-N 0.000 claims description 2
- NNFVGFXSJCCBRK-XIFFEERXSA-N (2s)-2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenyl]sulfonyl-methylamino]-3-(3-fluorophenyl)propanoic acid Chemical compound C([C@H](N(C)S(=O)(=O)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1C2=CC=CC=C2OC=1CC=1C=CC=CC=1)C(O)=O)C1=CC=CC(F)=C1 NNFVGFXSJCCBRK-XIFFEERXSA-N 0.000 claims description 2
- ZRECXQDSNGZOPR-XIFFEERXSA-N (2s)-2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenyl]sulfonyl-methylamino]-3-(4-fluorophenyl)propanoic acid Chemical compound C([C@H](N(C)S(=O)(=O)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1C2=CC=CC=C2OC=1CC=1C=CC=CC=1)C(O)=O)C1=CC=C(F)C=C1 ZRECXQDSNGZOPR-XIFFEERXSA-N 0.000 claims description 2
- DUJKEHAVYGLFTH-XIFFEERXSA-N (2s)-2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenyl]sulfonyl-methylamino]-3-phenylpropanoic acid Chemical compound C([C@H](N(C)S(=O)(=O)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1C2=CC=CC=C2OC=1CC=1C=CC=CC=1)C(O)=O)C1=CC=CC=C1 DUJKEHAVYGLFTH-XIFFEERXSA-N 0.000 claims description 2
- ZVKRFSNAJWLMPK-YTTGMZPUSA-N (2s)-2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenyl]sulfonylamino]-3-(3-fluorophenyl)propanoic acid Chemical compound C([C@@H](C(=O)O)NS(=O)(=O)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1C2=CC=CC=C2OC=1CC=1C=CC=CC=1)C1=CC=CC(F)=C1 ZVKRFSNAJWLMPK-YTTGMZPUSA-N 0.000 claims description 2
- MXGLLBXKUZEPRM-YTTGMZPUSA-N (2s)-2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenyl]sulfonylamino]-3-(4-fluorophenyl)propanoic acid Chemical compound C([C@@H](C(=O)O)NS(=O)(=O)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1C2=CC=CC=C2OC=1CC=1C=CC=CC=1)C1=CC=C(F)C=C1 MXGLLBXKUZEPRM-YTTGMZPUSA-N 0.000 claims description 2
- POXAPKDSOPLBBL-YTTGMZPUSA-N (2s)-2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenyl]sulfonylamino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NS(=O)(=O)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1C2=CC=CC=C2OC=1CC=1C=CC=CC=1)C1=CC=CC=C1 POXAPKDSOPLBBL-YTTGMZPUSA-N 0.000 claims description 2
- RSVSZFODKAFGLI-LJAQVGFWSA-N (2s)-2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenyl]sulfonylamino]-4-methylpentanoic acid Chemical compound C1=CC(S(=O)(=O)N[C@@H](CC(C)C)C(O)=O)=CC=C1C1=CC=C(C=2C3=CC=CC=C3OC=2CC=2C=CC=CC=2)C=C1 RSVSZFODKAFGLI-LJAQVGFWSA-N 0.000 claims description 2
- XYZCEZUHZMQLDP-FQEVSTJZSA-N (2s)-2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenyl]sulfonylamino]propanoic acid Chemical compound C1=CC(S(=O)(=O)N[C@@H](C)C(O)=O)=CC=C1C1=CC=C(C=2C3=CC=CC=C3OC=2CC=2C=CC=CC=2)C=C1 XYZCEZUHZMQLDP-FQEVSTJZSA-N 0.000 claims description 2
- NOCKIGVUZLZBOZ-NDEPHWFRSA-N (2s)-2-[[4-[4-(5-methylindol-1-yl)phenyl]benzoyl]amino]-3-phenylpropanoic acid Chemical compound C([C@H](NC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)N1C2=CC=C(C=C2C=C1)C)C(O)=O)C1=CC=CC=C1 NOCKIGVUZLZBOZ-NDEPHWFRSA-N 0.000 claims description 2
- QVQXHODTLOOOCB-YTTGMZPUSA-N (2s)-2-[[4-[4-[(2-butyl-1-benzofuran-3-yl)methyl]phenyl]benzoyl]-methylamino]-3-phenylpropanoic acid Chemical compound C([C@H](N(C)C(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)CC=1C2=CC=CC=C2OC=1CCCC)C(O)=O)C1=CC=CC=C1 QVQXHODTLOOOCB-YTTGMZPUSA-N 0.000 claims description 2
- JYDNEWUUQHTPMP-YTTGMZPUSA-N (2s)-2-[[4-[4-[(2-butyl-1-benzofuran-3-yl)methyl]phenyl]phenyl]sulfonyl-methylamino]-3-phenylpropanoic acid Chemical compound C([C@H](N(C)S(=O)(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)CC=1C2=CC=CC=C2OC=1CCCC)C(O)=O)C1=CC=CC=C1 JYDNEWUUQHTPMP-YTTGMZPUSA-N 0.000 claims description 2
- LHKBJCSEDWDFQU-UHFFFAOYSA-N 2-[3-chloro-4-(4-dibenzofuran-4-ylphenyl)phenoxy]-2-phenylacetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C3=C(C4=CC=CC=C4O3)C=CC=2)C(Cl)=CC=1OC(C(=O)O)C1=CC=CC=C1 LHKBJCSEDWDFQU-UHFFFAOYSA-N 0.000 claims description 2
- UHAOLYKGVURGHY-UHFFFAOYSA-N 2-[4-(1-benzylindol-6-yl)phenoxy]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OC(C=C1)=CC=C1C(C=C12)=CC=C1C=CN2CC1=CC=CC=C1 UHAOLYKGVURGHY-UHFFFAOYSA-N 0.000 claims description 2
- QQYFRIAAVHUCJW-UHFFFAOYSA-N 2-[4-(4-dibenzofuran-4-ylphenyl)-3-(trifluoromethyl)phenoxy]-2-phenylacetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C3=C(C4=CC=CC=C4O3)C=CC=2)C(C(F)(F)F)=CC=1OC(C(=O)O)C1=CC=CC=C1 QQYFRIAAVHUCJW-UHFFFAOYSA-N 0.000 claims description 2
- OZTCLTRYZGGMDA-UHFFFAOYSA-N 2-[4-(4-dibenzofuran-4-ylphenyl)phenoxy]-2-phenylacetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C3=C(C4=CC=CC=C4O3)C=CC=2)C=CC=1OC(C(=O)O)C1=CC=CC=C1 OZTCLTRYZGGMDA-UHFFFAOYSA-N 0.000 claims description 2
- RKZNTKWULWPQCU-UHFFFAOYSA-N 2-[4-(4-dibenzothiophen-4-ylphenyl)phenoxy]-2-phenylacetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C3=C(C4=CC=CC=C4S3)C=CC=2)C=CC=1OC(C(=O)O)C1=CC=CC=C1 RKZNTKWULWPQCU-UHFFFAOYSA-N 0.000 claims description 2
- PVFRKJHMBYMZRC-UHFFFAOYSA-N 2-[4-(4-indol-1-ylphenyl)phenoxy]-2-phenylacetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C=C2)C=CC=1OC(C(=O)O)C1=CC=CC=C1 PVFRKJHMBYMZRC-UHFFFAOYSA-N 0.000 claims description 2
- SQMLYPGVSZMVOH-UHFFFAOYSA-N 2-[4-[4-(1-benzofuran-2-yl)phenyl]phenoxy]-2-phenylacetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2OC3=CC=CC=C3C=2)C=CC=1OC(C(=O)O)C1=CC=CC=C1 SQMLYPGVSZMVOH-UHFFFAOYSA-N 0.000 claims description 2
- KSKAMSSJHOSHJP-UHFFFAOYSA-N 2-[4-[4-(1-benzothiophen-3-yl)phenyl]phenoxy]-2-phenylacetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C3=CC=CC=C3SC=2)C=CC=1OC(C(=O)O)C1=CC=CC=C1 KSKAMSSJHOSHJP-UHFFFAOYSA-N 0.000 claims description 2
- HHLFYYQYYWYHRW-UHFFFAOYSA-N 2-[4-[4-(1-benzylindol-5-yl)phenyl]phenoxy]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OC(C=C1)=CC=C1C(C=C1)=CC=C1C(C=C1C=C2)=CC=C1N2CC1=CC=CC=C1 HHLFYYQYYWYHRW-UHFFFAOYSA-N 0.000 claims description 2
- QCVMHQBNRWYXOD-UHFFFAOYSA-N 2-[4-[4-(1-butylindolizin-2-yl)phenyl]anilino]-2-phenylacetic acid Chemical compound C=1N2C=CC=CC2=C(CCCC)C=1C(C=C1)=CC=C1C(C=C1)=CC=C1NC(C(O)=O)C1=CC=CC=C1 QCVMHQBNRWYXOD-UHFFFAOYSA-N 0.000 claims description 2
- QJPDJMOOIBYJFT-UHFFFAOYSA-N 2-[4-[4-(1-butylindolizin-2-yl)phenyl]phenoxy]-2-phenylacetic acid Chemical compound C=1N2C=CC=CC2=C(CCCC)C=1C(C=C1)=CC=C1C(C=C1)=CC=C1OC(C(O)=O)C1=CC=CC=C1 QJPDJMOOIBYJFT-UHFFFAOYSA-N 0.000 claims description 2
- DTLZRYDPCAKNOU-UHFFFAOYSA-N 2-[4-[4-(1-butylindolizin-2-yl)phenyl]phenoxy]propanoic acid Chemical compound C=1N2C=CC=CC2=C(CCCC)C=1C(C=C1)=CC=C1C1=CC=C(OC(C)C(O)=O)C=C1 DTLZRYDPCAKNOU-UHFFFAOYSA-N 0.000 claims description 2
- FESFWYIPANZSEP-UHFFFAOYSA-N 2-[4-[4-(1-butylindolizin-2-yl)phenyl]phenyl]sulfonyl-2-phenylacetic acid Chemical compound C=1N2C=CC=CC2=C(CCCC)C=1C(C=C1)=CC=C1C(C=C1)=CC=C1S(=O)(=O)C(C(O)=O)C1=CC=CC=C1 FESFWYIPANZSEP-UHFFFAOYSA-N 0.000 claims description 2
- VZQPGBMZSRZGNS-UHFFFAOYSA-N 2-[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]-2-nitroanilino]-3-phenylpropanoic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C3=CC=CC=C3OC=2CC=2C=CC=CC=2)C=C([N+]([O-])=O)C=1NC(C(=O)O)CC1=CC=CC=C1 VZQPGBMZSRZGNS-UHFFFAOYSA-N 0.000 claims description 2
- CBAKPPAEHFOGJA-UHFFFAOYSA-N 2-[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenoxy]-3-phenylpropanoic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C3=CC=CC=C3OC=2CC=2C=CC=CC=2)C=CC=1OC(C(=O)O)CC1=CC=CC=C1 CBAKPPAEHFOGJA-UHFFFAOYSA-N 0.000 claims description 2
- PUBMZUOBSIJWOM-UHFFFAOYSA-N 2-[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1C1=CC=C(C=2C3=CC=CC=C3OC=2CC=2C=CC=CC=2)C=C1 PUBMZUOBSIJWOM-UHFFFAOYSA-N 0.000 claims description 2
- CPNWIHWVKIGEIY-UHFFFAOYSA-N 2-[4-[4-(5-chloroindol-1-yl)phenyl]phenoxy]-2-phenylacetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)N2C3=CC=C(Cl)C=C3C=C2)C=CC=1OC(C(=O)O)C1=CC=CC=C1 CPNWIHWVKIGEIY-UHFFFAOYSA-N 0.000 claims description 2
- ZNNQOHFMKNTICX-UHFFFAOYSA-N 2-[4-[4-(5-methylindol-1-yl)phenyl]phenoxy]-2-phenylacetic acid Chemical compound C1=CC2=CC(C)=CC=C2N1C(C=C1)=CC=C1C(C=C1)=CC=C1OC(C(O)=O)C1=CC=CC=C1 ZNNQOHFMKNTICX-UHFFFAOYSA-N 0.000 claims description 2
- QQNUVDFADZMUMM-UHFFFAOYSA-N 2-[4-[4-[(9-oxofluoren-1-yl)oxymethyl]phenyl]phenoxy]-2-phenylacetic acid Chemical compound C=1C=C(C=2C=CC(COC=3C=4C(=O)C5=CC=CC=C5C=4C=CC=3)=CC=2)C=CC=1OC(C(=O)O)C1=CC=CC=C1 QQNUVDFADZMUMM-UHFFFAOYSA-N 0.000 claims description 2
- WHASZUKPNPIWMA-UHFFFAOYSA-N 2-[4-[4-[2-(1,3-benzoxazol-2-yl)phenyl]phenyl]phenoxy]-2-phenylacetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C(=CC=CC=2)C=2OC3=CC=CC=C3N=2)C=CC=1OC(C(=O)O)C1=CC=CC=C1 WHASZUKPNPIWMA-UHFFFAOYSA-N 0.000 claims description 2
- YPIRSCGUZYBDQH-UHFFFAOYSA-N 2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenyl]sulfonyl-[[3-(trifluoromethyl)phenyl]methyl]amino]butanoic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C3=CC=CC=C3OC=2CC=2C=CC=CC=2)C=CC=1S(=O)(=O)N(C(CC)C(O)=O)CC1=CC=CC(C(F)(F)F)=C1 YPIRSCGUZYBDQH-UHFFFAOYSA-N 0.000 claims description 2
- XYEFJDMJYCPCII-UHFFFAOYSA-N 2-[benzyl-[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenyl]sulfonylamino]acetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C3=CC=CC=C3OC=2CC=2C=CC=CC=2)C=CC=1S(=O)(=O)N(CC(=O)O)CC1=CC=CC=C1 XYEFJDMJYCPCII-UHFFFAOYSA-N 0.000 claims description 2
- CNEKYBTXUMIHHG-UHFFFAOYSA-N 3-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]benzoyl]amino]butanoic acid Chemical compound C1=CC(C(=O)NC(CC(O)=O)C)=CC=C1C1=CC=C(C=2C3=CC=CC=C3OC=2CC=2C=CC=CC=2)C=C1 CNEKYBTXUMIHHG-UHFFFAOYSA-N 0.000 claims description 2
- XWPMVHQMDVXBDB-UHFFFAOYSA-N 4-(4-dibenzofuran-4-ylphenyl)-4-oxo-2-[[3-(trifluoromethyl)phenyl]methyl]butanoic acid Chemical compound C=1C=C(C=2C3=C(C4=CC=CC=C4O3)C=CC=2)C=CC=1C(=O)CC(C(=O)O)CC1=CC=CC(C(F)(F)F)=C1 XWPMVHQMDVXBDB-UHFFFAOYSA-N 0.000 claims description 2
- BVVWCVAFOUVSLH-UHFFFAOYSA-N C=1C=C(C=2C=CC(=CC=2)C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=CC=1CON=C(CC(=O)O)C1=CC=CC=C1 Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=CC=1CON=C(CC(=O)O)C1=CC=CC=C1 BVVWCVAFOUVSLH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- SSAQFHYJPWVVMQ-XIFFEERXSA-N ethyl (2s)-2-[[4-[4-(1-butylindolizin-2-yl)phenyl]benzoyl]amino]-3-phenylpropanoate Chemical compound C([C@H](NC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)C=1C(=C2C=CC=CN2C=1)CCCC)C(=O)OCC)C1=CC=CC=C1 SSAQFHYJPWVVMQ-XIFFEERXSA-N 0.000 claims description 2
- JVRMASRCOAIISL-DHUJRADRSA-N ethyl (2s)-2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenyl]sulfonyl-methylamino]-3-phenylpropanoate Chemical compound C([C@@H](C(=O)OCC)N(C)S(=O)(=O)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1C2=CC=CC=C2OC=1CC=1C=CC=CC=1)C1=CC=CC=C1 JVRMASRCOAIISL-DHUJRADRSA-N 0.000 claims description 2
- YYKVWSSLOPRIFV-UHFFFAOYSA-N ethyl 2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenyl]sulfonylamino]-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)NS(=O)(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1C(C1=CC=CC=C1O1)=C1CC1=CC=CC=C1 YYKVWSSLOPRIFV-UHFFFAOYSA-N 0.000 claims description 2
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 2
- GOJVWLJXXMZQMI-UHFFFAOYSA-N methyl 2-(4-naphtho[3,2-b][1]benzofuran-11-ylphenoxy)propanoate Chemical compound C1=CC(OC(C)C(=O)OC)=CC=C1C1=C2C3=CC=CC=C3OC2=CC2=CC=CC=C12 GOJVWLJXXMZQMI-UHFFFAOYSA-N 0.000 claims description 2
- BXTZNECSSGCFGY-UHFFFAOYSA-N methyl 2-[4-[4-(1-benzofuran-2-yl)phenyl]phenoxy]-2-phenylacetate Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2OC3=CC=CC=C3C=2)C=CC=1OC(C(=O)OC)C1=CC=CC=C1 BXTZNECSSGCFGY-UHFFFAOYSA-N 0.000 claims description 2
- AZRGQGBUQRSTGD-UHFFFAOYSA-N methyl 2-[4-[4-(1-benzylindol-5-yl)phenyl]phenoxy]-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C(=O)OC)OC(C=C1)=CC=C1C(C=C1)=CC=C1C(C=C1C=C2)=CC=C1N2CC1=CC=CC=C1 AZRGQGBUQRSTGD-UHFFFAOYSA-N 0.000 claims description 2
- RMWMMNSXLJCHAU-UHFFFAOYSA-N methyl 2-[4-[4-(1-benzylindol-6-yl)phenyl]phenoxy]-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C(=O)OC)OC(C=C1)=CC=C1C(C=C1)=CC=C1C(C=C12)=CC=C1C=CN2CC1=CC=CC=C1 RMWMMNSXLJCHAU-UHFFFAOYSA-N 0.000 claims description 2
- KIQNHLZNRDWUMP-UHFFFAOYSA-N methyl 2-[4-[4-(1-butylindolizin-2-yl)phenyl]phenyl]sulfonyl-2-phenylacetate Chemical compound C=1N2C=CC=CC2=C(CCCC)C=1C(C=C1)=CC=C1C(C=C1)=CC=C1S(=O)(=O)C(C(=O)OC)C1=CC=CC=C1 KIQNHLZNRDWUMP-UHFFFAOYSA-N 0.000 claims description 2
- SGPSKBLLMIGOLM-UHFFFAOYSA-N methyl 2-[4-[4-[(2-benzoylphenoxy)methyl]phenyl]phenoxy]-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C(=O)OC)OC(C=C1)=CC=C1C(C=C1)=CC=C1COC1=CC=CC=C1C(=O)C1=CC=CC=C1 SGPSKBLLMIGOLM-UHFFFAOYSA-N 0.000 claims description 2
- GPNPPRXNPRQBAM-UHFFFAOYSA-N methyl 2-[4-[4-[(2-benzylphenoxy)methyl]phenyl]phenoxy]-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C(=O)OC)OC(C=C1)=CC=C1C(C=C1)=CC=C1COC1=CC=CC=C1CC1=CC=CC=C1 GPNPPRXNPRQBAM-UHFFFAOYSA-N 0.000 claims description 2
- 125000002071 phenylalkoxy group Chemical group 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- NHIMACVYYZIWJC-UMSFTDKQSA-N (2s)-2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]phenyl]sulfonyl-ethylamino]-3-(4-fluorophenyl)propanoic acid Chemical compound C([C@H](N(CC)S(=O)(=O)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1C2=CC=CC=C2OC=1CC=1C=CC=CC=1)C(O)=O)C1=CC=C(F)C=C1 NHIMACVYYZIWJC-UMSFTDKQSA-N 0.000 claims 1
- CPYOVRVBMTZDAG-SANMLTNESA-N (2s)-5-amino-2-[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]-2-nitroanilino]-5-oxopentanoic acid Chemical compound C1=C([N+]([O-])=O)C(N[C@@H](CCC(=O)N)C(O)=O)=CC=C1C1=CC=C(C=2C3=CC=CC=C3OC=2CC=2C=CC=CC=2)C=C1 CPYOVRVBMTZDAG-SANMLTNESA-N 0.000 claims 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
- LIKQUXALWNYQST-UHFFFAOYSA-N 2-[2-chloro-4-(4-dibenzofuran-4-ylphenyl)phenoxy]-2-phenylacetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C3=C(C4=CC=CC=C4O3)C=CC=2)C=C(Cl)C=1OC(C(=O)O)C1=CC=CC=C1 LIKQUXALWNYQST-UHFFFAOYSA-N 0.000 claims 1
- XNIYTDCYFRYSBN-UHFFFAOYSA-N 2-[4-(4-dibenzofuran-4-ylphenyl)-2-fluorophenoxy]-2-phenylacetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C3=C(C4=CC=CC=C4O3)C=CC=2)C=C(F)C=1OC(C(=O)O)C1=CC=CC=C1 XNIYTDCYFRYSBN-UHFFFAOYSA-N 0.000 claims 1
- GSUCSJIGNHMJKC-UHFFFAOYSA-N 2-[4-(4-dibenzofuran-4-ylphenyl)-3-methylphenoxy]-2-phenylacetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C3=C(C4=CC=CC=C4O3)C=CC=2)C(C)=CC=1OC(C(O)=O)C1=CC=CC=C1 GSUCSJIGNHMJKC-UHFFFAOYSA-N 0.000 claims 1
- UTEAUCDPBZAWGI-UHFFFAOYSA-N 2-[4-[4-(1-benzothiophen-2-yl)phenyl]phenoxy]-2-phenylacetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2SC3=CC=CC=C3C=2)C=CC=1OC(C(=O)O)C1=CC=CC=C1 UTEAUCDPBZAWGI-UHFFFAOYSA-N 0.000 claims 1
- OQDDQVVATCIZAD-UHFFFAOYSA-N 2-[4-[4-(1-benzylindol-6-yl)phenyl]phenoxy]-2-phenylacetic acid 4-[4-(4-dibenzofuran-4-ylphenyl)phenyl]-4-oxo-2-[[3-(trifluoromethyl)phenyl]methyl]butanoic acid Chemical compound C(C1=CC=CC=C1)N1C=CC2=CC=C(C=C12)C1=CC=C(C=C1)C1=CC=C(C=C1)OC(C(=O)O)C1=CC=CC=C1.C1=CC=C(C=2OC3=C(C21)C=CC=C3)C3=CC=C(C=C3)C3=CC=C(C=C3)C(CC(C(=O)O)CC3=CC(=CC=C3)C(F)(F)F)=O OQDDQVVATCIZAD-UHFFFAOYSA-N 0.000 claims 1
- QECPNSUUEYVMAI-UHFFFAOYSA-N 2-[[4-(2-dibenzofuran-4-yl-1,3-thiazol-4-yl)phenyl]sulfonyl-ethylamino]-3-phenylpropanoic acid Chemical compound C=1C=C(C=2N=C(SC=2)C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=CC=1S(=O)(=O)N(CC)C(C(O)=O)CC1=CC=CC=C1 QECPNSUUEYVMAI-UHFFFAOYSA-N 0.000 claims 1
- FYGNDRLHDRXPDZ-UHFFFAOYSA-N 2-[[4-(4-dibenzofuran-4-ylphenyl)phenyl]methoxyimino]-2-phenylacetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=CC=1CON=C(C(=O)O)C1=CC=CC=C1 FYGNDRLHDRXPDZ-UHFFFAOYSA-N 0.000 claims 1
- YGUFREKTZUPJMX-UHFFFAOYSA-N 2-[[4-(4-dibenzofuran-4-ylphenyl)phenyl]sulfonylamino]-2-phenylacetic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C3=C(C4=CC=CC=C4O3)C=CC=2)C=CC=1S(=O)(=O)NC(C(=O)O)C1=CC=CC=C1 YGUFREKTZUPJMX-UHFFFAOYSA-N 0.000 claims 1
- IPAXGSIXWVRGDU-UHFFFAOYSA-N 2-[[4-(4-dibenzofuran-4-ylphenyl)phenyl]sulfonylamino]-3-phenylpropanoic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C3=C(C4=CC=CC=C4O3)C=CC=2)C=CC=1S(=O)(=O)NC(C(=O)O)CC1=CC=CC=C1 IPAXGSIXWVRGDU-UHFFFAOYSA-N 0.000 claims 1
- JBPANPVYVLBQAD-UHFFFAOYSA-N 2-[[4-[4-(2-benzyl-1-benzofuran-3-yl)phenyl]-2-fluorophenyl]sulfonyl-methylamino]-3-phenylpropanoic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2C3=CC=CC=C3OC=2CC=2C=CC=CC=2)C=C(F)C=1S(=O)(=O)N(C)C(C(O)=O)CC1=CC=CC=C1 JBPANPVYVLBQAD-UHFFFAOYSA-N 0.000 claims 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers
- C07C69/736—Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/92—Naphthofurans; Hydrogenated naphthofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46705703P | 2003-04-30 | 2003-04-30 | |
| US60/467,057 | 2003-04-30 | ||
| PCT/US2004/011371 WO2004099168A2 (en) | 2003-04-30 | 2004-04-14 | Substituted carboxylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2523714A1 true CA2523714A1 (en) | 2004-11-18 |
Family
ID=33435014
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002523714A Abandoned CA2523714A1 (en) | 2003-04-30 | 2004-04-14 | Substituted carboxylic acids |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US7358364B2 (enExample) |
| EP (1) | EP1620420A2 (enExample) |
| JP (1) | JP2006525329A (enExample) |
| KR (1) | KR20060006953A (enExample) |
| CN (1) | CN1812977A (enExample) |
| AU (1) | AU2004236173B2 (enExample) |
| BR (1) | BRPI0409914A (enExample) |
| CA (1) | CA2523714A1 (enExample) |
| EA (1) | EA200501710A1 (enExample) |
| MX (1) | MXPA05011524A (enExample) |
| NO (1) | NO20054957L (enExample) |
| WO (1) | WO2004099168A2 (enExample) |
| ZA (1) | ZA200509631B (enExample) |
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| JP2006525329A (ja) | 2003-04-30 | 2006-11-09 | ジ インスチチュート フォー ファーマシューティカル ディスカバリー、エルエルシー | 置換カルボン酸類 |
| US7582773B2 (en) * | 2003-09-25 | 2009-09-01 | Wyeth | Substituted phenyl indoles |
| FR2869615B1 (fr) * | 2004-05-03 | 2007-11-16 | Merck Sante Soc Par Actions Si | Derives de l'acide butanoique, procedes pour leur preparation, compositions pharmaceutiques les contenant et leurs applications therapeutiques |
| JP2008506702A (ja) | 2004-07-14 | 2008-03-06 | ピーティーシー セラピューティクス，インコーポレーテッド | Ｃ型肝炎を治療するための方法 |
| US7772271B2 (en) | 2004-07-14 | 2010-08-10 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| US7781478B2 (en) | 2004-07-14 | 2010-08-24 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| US7868037B2 (en) | 2004-07-14 | 2011-01-11 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| NZ553329A (en) | 2004-07-22 | 2010-09-30 | Ptc Therapeutics Inc | Thienopyridines for treating hepatitis C |
| JP2008518937A (ja) * | 2004-10-28 | 2008-06-05 | ジ インスティチューツ フォー ファーマシューティカル ディスカバリー、エルエルシー | 置換カルボン酸 |
| JP2008520692A (ja) * | 2004-11-18 | 2008-06-19 | ジ インスチチュート フォー ファーマシューティカル ディスカバリー、エルエルシー | 複素環置換カルボン酸 |
| CN102775396B (zh) | 2005-11-08 | 2014-10-08 | 沃泰克斯药物股份有限公司 | Atp-结合弹夹转运蛋白的杂环调控剂 |
| US7671221B2 (en) | 2005-12-28 | 2010-03-02 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-Binding Cassette transporters |
| WO2007109851A1 (en) | 2006-03-29 | 2007-10-04 | Velacor Therapeutics Pty Ltd | Treatment of neurodegenerative diseases |
| US7754739B2 (en) | 2007-05-09 | 2010-07-13 | Vertex Pharmaceuticals Incorporated | Modulators of CFTR |
| WO2008119109A1 (en) | 2007-03-29 | 2008-10-09 | Velacor Therapeutics Pty Ltd | Treatment of neurological disorders |
| JP5497633B2 (ja) | 2007-05-09 | 2014-05-21 | バーテックス ファーマシューティカルズ インコーポレイテッド | Ｃｆｔｒのモジュレーター |
| EP2231606B1 (en) | 2007-12-07 | 2013-02-13 | Vertex Pharmaceuticals Incorporated | Processes for producing cycloalkylcarboxiamido-pyridine benzoic acids |
| NZ614151A (en) | 2007-12-07 | 2015-04-24 | Vertex Pharma | Solid forms of 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid |
| ES2647531T3 (es) | 2008-02-28 | 2017-12-22 | Vertex Pharmaceuticals Incorporated | Derivados de heteroarilo como moduladores de CFTR |
| UA103319C2 (en) | 2008-05-06 | 2013-10-10 | Глаксосмитклайн Ллк | Thiazole- and oxazole-benzene sulfonamide compounds |
| ES3017582T3 (en) | 2010-04-07 | 2025-05-13 | Vertex Pharma | Pharmaceutical compositions of 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyriodin-2-yl)benzoic acid and administration thereof |
| RU2538964C1 (ru) | 2010-12-17 | 2015-01-10 | Мицубиси Танабе Фарма Корпорейшн | Соединение с последовательной арициклической структурой, обладающее активностью ингибирования ацилкофермента а: диацилглицеринацилтрансферазы (dgat1) |
| EP2862856B1 (en) | 2012-06-15 | 2018-08-01 | Mitsubishi Tanabe Pharma Corporation | Imidazole and triazole compounds as dgat-1 inhibitors |
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| CN105848657B (zh) | 2013-11-12 | 2020-05-22 | 沃泰克斯药物股份有限公司 | 制备用于治疗cftr介导的疾病的药物组合物的方法 |
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-
2004
- 2004-04-14 JP JP2006509981A patent/JP2006525329A/ja active Pending
- 2004-04-14 MX MXPA05011524A patent/MXPA05011524A/es not_active Application Discontinuation
- 2004-04-14 EA EA200501710A patent/EA200501710A1/ru unknown
- 2004-04-14 EP EP04760538A patent/EP1620420A2/en not_active Withdrawn
- 2004-04-14 CN CNA2004800184160A patent/CN1812977A/zh active Pending
- 2004-04-14 WO PCT/US2004/011371 patent/WO2004099168A2/en not_active Ceased
- 2004-04-14 AU AU2004236173A patent/AU2004236173B2/en not_active Ceased
- 2004-04-14 KR KR1020057020613A patent/KR20060006953A/ko not_active Withdrawn
- 2004-04-14 CA CA002523714A patent/CA2523714A1/en not_active Abandoned
- 2004-04-14 US US10/823,842 patent/US7358364B2/en not_active Expired - Fee Related
- 2004-04-14 BR BRPI0409914-1A patent/BRPI0409914A/pt not_active IP Right Cessation
-
2005
- 2005-10-25 NO NO20054957A patent/NO20054957L/no not_active Application Discontinuation
- 2005-11-29 ZA ZA200509631A patent/ZA200509631B/en unknown
-
2008
- 2008-04-15 US US12/103,082 patent/US20090082392A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| NO20054957L (no) | 2006-01-23 |
| MXPA05011524A (es) | 2006-03-21 |
| EA200501710A1 (ru) | 2006-06-30 |
| US20090082392A1 (en) | 2009-03-26 |
| WO2004099168A3 (en) | 2005-02-24 |
| AU2004236173B2 (en) | 2008-07-03 |
| BRPI0409914A (pt) | 2006-04-25 |
| WO2004099168A2 (en) | 2004-11-18 |
| NO20054957D0 (no) | 2005-10-25 |
| US20040266788A1 (en) | 2004-12-30 |
| CN1812977A (zh) | 2006-08-02 |
| EP1620420A2 (en) | 2006-02-01 |
| AU2004236173A1 (en) | 2004-11-18 |
| KR20060006953A (ko) | 2006-01-20 |
| ZA200509631B (en) | 2007-02-28 |
| US7358364B2 (en) | 2008-04-15 |
| JP2006525329A (ja) | 2006-11-09 |
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