JP2006522118A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2006522118A5 JP2006522118A5 JP2006508007A JP2006508007A JP2006522118A5 JP 2006522118 A5 JP2006522118 A5 JP 2006522118A5 JP 2006508007 A JP2006508007 A JP 2006508007A JP 2006508007 A JP2006508007 A JP 2006508007A JP 2006522118 A5 JP2006522118 A5 JP 2006522118A5
- Authority
- JP
- Japan
- Prior art keywords
- oxy
- acetic acid
- biphenyl
- trifluoromethyl
- methyl
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 5
- HLHVPJVNRURVNK-UHFFFAOYSA-N 2-(4-cyano-2-phenylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(C#N)C=C1C1=CC=CC=C1 HLHVPJVNRURVNK-UHFFFAOYSA-N 0.000 claims description 3
- AWOLOLKCVZPBPS-UHFFFAOYSA-N 2-(4-nitro-2-phenylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C([N+]([O-])=O)C=C1C1=CC=CC=C1 AWOLOLKCVZPBPS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 17
- 150000002367 halogens Chemical class 0.000 claims 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 10
- 125000001424 substituent group Chemical group 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 5
- 235000010290 biphenyl Nutrition 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 208000023504 respiratory system disease Diseases 0.000 claims 2
- 239000011734 sodium Chemical class 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- UTDANZPJNOWLLZ-GFCCVEGCSA-N (2r)-2-[2-(4-ethylsulfonyl-2-methylphenyl)-4-(trifluoromethyl)phenoxy]propanoic acid Chemical compound CC1=CC(S(=O)(=O)CC)=CC=C1C1=CC(C(F)(F)F)=CC=C1O[C@H](C)C(O)=O UTDANZPJNOWLLZ-GFCCVEGCSA-N 0.000 claims 1
- UVUBPIDMHFSLPL-QMMMGPOBSA-N (2s)-2-[2-(2,4-dichlorophenyl)-4-fluorophenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(F)C=C1C1=CC=C(Cl)C=C1Cl UVUBPIDMHFSLPL-QMMMGPOBSA-N 0.000 claims 1
- GBVPNEKWRGIPPU-JTQLQIEISA-N (2s)-2-[2-(2-chloro-4-ethylsulfonylphenyl)-4-(trifluoromethyl)phenoxy]propanoic acid Chemical compound ClC1=CC(S(=O)(=O)CC)=CC=C1C1=CC(C(F)(F)F)=CC=C1O[C@@H](C)C(O)=O GBVPNEKWRGIPPU-JTQLQIEISA-N 0.000 claims 1
- LJIYOGZCGKFGDT-VIFPVBQESA-N (2s)-2-[2-(2-chloro-4-methylsulfonylphenyl)-4-(trifluoromethyl)phenoxy]propanoic acid Chemical class OC(=O)[C@H](C)OC1=CC=C(C(F)(F)F)C=C1C1=CC=C(S(C)(=O)=O)C=C1Cl LJIYOGZCGKFGDT-VIFPVBQESA-N 0.000 claims 1
- CUQMQTKLLBWIKJ-VIFPVBQESA-N (2s)-2-[2-(2-chloro-4-methylsulfonylphenyl)-4-fluorophenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(F)C=C1C1=CC=C(S(C)(=O)=O)C=C1Cl CUQMQTKLLBWIKJ-VIFPVBQESA-N 0.000 claims 1
- DQZYOGMMSWYWDD-VIFPVBQESA-N (2s)-2-[2-(2-fluoro-4-methylsulfonylphenyl)-4-(trifluoromethyl)phenoxy]propanoic acid Chemical class OC(=O)[C@H](C)OC1=CC=C(C(F)(F)F)C=C1C1=CC=C(S(C)(=O)=O)C=C1F DQZYOGMMSWYWDD-VIFPVBQESA-N 0.000 claims 1
- NGANXYIPATXYJN-JTQLQIEISA-N (2s)-2-[2-(3-cyanophenyl)-4-(trifluoromethyl)phenoxy]propanoic acid Chemical class OC(=O)[C@H](C)OC1=CC=C(C(F)(F)F)C=C1C1=CC=CC(C#N)=C1 NGANXYIPATXYJN-JTQLQIEISA-N 0.000 claims 1
- RHKNWNBFQHQDBE-JTQLQIEISA-N (2s)-2-[2-(3-cyanophenyl)-4-fluorophenoxy]propanoic acid Chemical class OC(=O)[C@H](C)OC1=CC=C(F)C=C1C1=CC=CC(C#N)=C1 RHKNWNBFQHQDBE-JTQLQIEISA-N 0.000 claims 1
- UTDANZPJNOWLLZ-LBPRGKRZSA-N (2s)-2-[2-(4-ethylsulfonyl-2-methylphenyl)-4-(trifluoromethyl)phenoxy]propanoic acid Chemical compound CC1=CC(S(=O)(=O)CC)=CC=C1C1=CC(C(F)(F)F)=CC=C1O[C@@H](C)C(O)=O UTDANZPJNOWLLZ-LBPRGKRZSA-N 0.000 claims 1
- PTMHUXOQMHNGBN-VIFPVBQESA-N (2s)-2-[2-[2-(methanesulfonamido)-4-methylpyrimidin-5-yl]-4-(trifluoromethyl)phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(C(F)(F)F)C=C1C1=CN=C(NS(C)(=O)=O)N=C1C PTMHUXOQMHNGBN-VIFPVBQESA-N 0.000 claims 1
- MQOYNPDGKWDYIJ-JTQLQIEISA-N (2s)-2-[2-[2-chloro-4-(dimethylsulfamoyl)phenyl]-4-(trifluoromethyl)phenoxy]propanoic acid Chemical class OC(=O)[C@H](C)OC1=CC=C(C(F)(F)F)C=C1C1=CC=C(S(=O)(=O)N(C)C)C=C1Cl MQOYNPDGKWDYIJ-JTQLQIEISA-N 0.000 claims 1
- QSQNIRJFLSUFBA-QMMMGPOBSA-N (2s)-2-[2-[2-chloro-5-(trifluoromethyl)phenyl]-4-fluorophenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(F)C=C1C1=CC(C(F)(F)F)=CC=C1Cl QSQNIRJFLSUFBA-QMMMGPOBSA-N 0.000 claims 1
- CHXYIRRYVLPDQC-LBPRGKRZSA-N (2s)-2-[2-[4-(azetidin-1-ylsulfonyl)phenyl]-4-chlorophenoxy]propanoic acid Chemical class OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1C1=CC=C(S(=O)(=O)N2CCC2)C=C1 CHXYIRRYVLPDQC-LBPRGKRZSA-N 0.000 claims 1
- GEAGOTGYCOZVOX-NSHDSACASA-N (2s)-2-[2-[4-(dimethylsulfamoyl)phenyl]-4-(trifluoromethyl)phenoxy]propanoic acid Chemical class OC(=O)[C@H](C)OC1=CC=C(C(F)(F)F)C=C1C1=CC=C(S(=O)(=O)N(C)C)C=C1 GEAGOTGYCOZVOX-NSHDSACASA-N 0.000 claims 1
- RASODJKPCNUMHP-JTQLQIEISA-N (2s)-2-[4-chloro-2-(2-chloro-4-ethylsulfonylphenyl)phenoxy]propanoic acid Chemical compound ClC1=CC(S(=O)(=O)CC)=CC=C1C1=CC(Cl)=CC=C1O[C@@H](C)C(O)=O RASODJKPCNUMHP-JTQLQIEISA-N 0.000 claims 1
- UAVDEXAEZZZLQK-VIFPVBQESA-N (2s)-2-[4-chloro-2-(2-chloro-4-methylsulfonylphenyl)phenoxy]propanoic acid Chemical class OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1C1=CC=C(S(C)(=O)=O)C=C1Cl UAVDEXAEZZZLQK-VIFPVBQESA-N 0.000 claims 1
- JAYZYFGLBVYVHG-VIFPVBQESA-N (2s)-2-[4-chloro-2-(2-fluoro-4-methylsulfonylphenyl)phenoxy]propanoic acid Chemical class OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1C1=CC=C(S(C)(=O)=O)C=C1F JAYZYFGLBVYVHG-VIFPVBQESA-N 0.000 claims 1
- SKDYMYFZHGVKDB-JTQLQIEISA-N (2s)-2-[4-chloro-2-(3-cyanophenyl)phenoxy]propanoic acid Chemical class OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1C1=CC=CC(C#N)=C1 SKDYMYFZHGVKDB-JTQLQIEISA-N 0.000 claims 1
- UIRDWYDLVOOGNI-ZDUSSCGKSA-N (2s)-2-[4-chloro-2-(4-morpholin-4-ylsulfonylphenyl)phenoxy]propanoic acid Chemical class OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1C1=CC=C(S(=O)(=O)N2CCOCC2)C=C1 UIRDWYDLVOOGNI-ZDUSSCGKSA-N 0.000 claims 1
- ZCMHFUQOLQDEDX-JTQLQIEISA-N (2s)-2-[4-chloro-2-[2-chloro-4-(dimethylsulfamoyl)phenyl]phenoxy]propanoic acid Chemical class OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1C1=CC=C(S(=O)(=O)N(C)C)C=C1Cl ZCMHFUQOLQDEDX-JTQLQIEISA-N 0.000 claims 1
- YYHSIEMPTBADSK-AWEZNQCLSA-N (2s)-2-[4-chloro-2-[2-methyl-4-(pyrrolidine-1-carbonyl)phenyl]phenoxy]propanoic acid Chemical class OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1C1=CC=C(C(=O)N2CCCC2)C=C1C YYHSIEMPTBADSK-AWEZNQCLSA-N 0.000 claims 1
- XMIUMZJUOMARHB-JTQLQIEISA-N (2s)-2-[4-chloro-2-[4-(dimethylsulfamoyl)-2-fluorophenyl]phenoxy]propanoic acid Chemical class OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1C1=CC=C(S(=O)(=O)N(C)C)C=C1F XMIUMZJUOMARHB-JTQLQIEISA-N 0.000 claims 1
- KSVZIQPZNUTVLS-NSHDSACASA-N (2s)-2-[4-chloro-2-[4-(dimethylsulfamoyl)phenyl]phenoxy]propanoic acid Chemical class OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1C1=CC=C(S(=O)(=O)N(C)C)C=C1 KSVZIQPZNUTVLS-NSHDSACASA-N 0.000 claims 1
- IKSINXPRXZPOQV-NSHDSACASA-N (2s)-2-[4-chloro-2-[4-methyl-6-[methyl(methylsulfonyl)amino]pyridin-3-yl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1C1=CN=C(N(C)S(C)(=O)=O)C=C1C IKSINXPRXZPOQV-NSHDSACASA-N 0.000 claims 1
- XUEHXEQKCGHAON-VIFPVBQESA-N (2s)-2-[4-cyano-2-(2,4-dichlorophenyl)phenoxy]propanoic acid Chemical class OC(=O)[C@H](C)OC1=CC=C(C#N)C=C1C1=CC=C(Cl)C=C1Cl XUEHXEQKCGHAON-VIFPVBQESA-N 0.000 claims 1
- DVEZYXONCGOUMF-VIFPVBQESA-N (2s)-2-[4-cyano-2-[2-fluoro-4-(trifluoromethyl)phenyl]phenoxy]propanoic acid Chemical class OC(=O)[C@H](C)OC1=CC=C(C#N)C=C1C1=CC=C(C(F)(F)F)C=C1F DVEZYXONCGOUMF-VIFPVBQESA-N 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- FUNQKWCUODOEJV-UHFFFAOYSA-N 2-(2,4-dibromo-6-phenylphenoxy)acetic acid Chemical compound OC(=O)COc1c(Br)cc(Br)cc1-c1ccccc1 FUNQKWCUODOEJV-UHFFFAOYSA-N 0.000 claims 1
- PXZGZXHJYIRBHW-UHFFFAOYSA-N 2-(4-bromo-2-phenylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C1=CC=CC=C1 PXZGZXHJYIRBHW-UHFFFAOYSA-N 0.000 claims 1
- UPWDVXOBZKNLLM-UHFFFAOYSA-N 2-(4-chloro-2-phenylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1C1=CC=CC=C1 UPWDVXOBZKNLLM-UHFFFAOYSA-N 0.000 claims 1
- ZGHICFNXOMIPLL-UHFFFAOYSA-N 2-(4-chloro-2-pyrimidin-5-ylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1C1=CN=CN=C1 ZGHICFNXOMIPLL-UHFFFAOYSA-N 0.000 claims 1
- DVEWANDODNREOY-UHFFFAOYSA-N 2-(4-chloro-2-quinolin-8-ylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1C1=CC=CC2=CC=CN=C12 DVEWANDODNREOY-UHFFFAOYSA-N 0.000 claims 1
- LCJVVYSSLAXKAG-UHFFFAOYSA-N 2-[2-(1,3-benzodioxol-5-yl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=C(OCO2)C2=C1 LCJVVYSSLAXKAG-UHFFFAOYSA-N 0.000 claims 1
- DVJPCOUAHFSSQB-UHFFFAOYSA-N 2-[2-(1-benzofuran-2-yl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC2=CC=CC=C2O1 DVJPCOUAHFSSQB-UHFFFAOYSA-N 0.000 claims 1
- UQRPLKIQZIEQGJ-UHFFFAOYSA-N 2-[2-(2,3-dichlorophenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=CC(Cl)=C1Cl UQRPLKIQZIEQGJ-UHFFFAOYSA-N 0.000 claims 1
- VBHCWDSHNIZODI-UHFFFAOYSA-N 2-[2-(2,4-dimethoxypyrimidin-5-yl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound COC1=NC(OC)=NC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O VBHCWDSHNIZODI-UHFFFAOYSA-N 0.000 claims 1
- LQJBEGARCXFPSB-UHFFFAOYSA-N 2-[2-(2,4-dimethylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=CC(C)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O LQJBEGARCXFPSB-UHFFFAOYSA-N 0.000 claims 1
- WONKNXVWKHKONP-UHFFFAOYSA-N 2-[2-(2,5-difluoro-4-methoxyphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound C1=C(F)C(OC)=CC(F)=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O WONKNXVWKHKONP-UHFFFAOYSA-N 0.000 claims 1
- HLUNPAVUYDODGZ-UHFFFAOYSA-N 2-[2-(2,5-difluoro-4-sulfamoylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound C1=C(F)C(S(=O)(=O)N)=CC(F)=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O HLUNPAVUYDODGZ-UHFFFAOYSA-N 0.000 claims 1
- JLSZZPIHSYZCJJ-UHFFFAOYSA-N 2-[2-(2,5-difluorophenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC(F)=CC=C1F JLSZZPIHSYZCJJ-UHFFFAOYSA-N 0.000 claims 1
- IETUONZSRMMZDK-UHFFFAOYSA-N 2-[2-(2,5-dimethylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=CC=C(C)C(C=2C(=CC=C(C=2)C(F)(F)F)OCC(O)=O)=C1 IETUONZSRMMZDK-UHFFFAOYSA-N 0.000 claims 1
- WVZDLNVAAOUNAU-UHFFFAOYSA-N 2-[2-(2-amino-4-methylpyrimidin-5-yl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=NC(N)=NC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O WVZDLNVAAOUNAU-UHFFFAOYSA-N 0.000 claims 1
- AWGSBBHCTCZVLR-UHFFFAOYSA-N 2-[2-(2-amino-5-methylpyridin-3-yl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=CN=C(N)C(C=2C(=CC=C(C=2)C(F)(F)F)OCC(O)=O)=C1 AWGSBBHCTCZVLR-UHFFFAOYSA-N 0.000 claims 1
- MOZQWBBHCHQDKF-UHFFFAOYSA-N 2-[2-(2-aminopyrimidin-5-yl)-4-chlorophenoxy]acetic acid Chemical compound C1=NC(N)=NC=C1C1=CC(Cl)=CC=C1OCC(O)=O MOZQWBBHCHQDKF-UHFFFAOYSA-N 0.000 claims 1
- BKMNDIUYMMHTDG-UHFFFAOYSA-N 2-[2-(2-chloro-4-ethylsulfonylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound ClC1=CC(S(=O)(=O)CC)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O BKMNDIUYMMHTDG-UHFFFAOYSA-N 0.000 claims 1
- GIMXNRWYMAQJKM-UHFFFAOYSA-N 2-[2-(2-chloro-4-hydroxyphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=C(O)C=C1Cl GIMXNRWYMAQJKM-UHFFFAOYSA-N 0.000 claims 1
- VAGPAMSZTPVNES-UHFFFAOYSA-N 2-[2-(2-chloro-5-methylpyridin-4-yl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=CN=C(Cl)C=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O VAGPAMSZTPVNES-UHFFFAOYSA-N 0.000 claims 1
- AKJMJSFQGHRPDO-UHFFFAOYSA-N 2-[2-(2-chloro-5-sulfamoylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound NS(=O)(=O)C1=CC=C(Cl)C(C=2C(=CC=C(C=2)C(F)(F)F)OCC(O)=O)=C1 AKJMJSFQGHRPDO-UHFFFAOYSA-N 0.000 claims 1
- CFRYRSBIQVJEGG-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=CC=C1Cl CFRYRSBIQVJEGG-UHFFFAOYSA-N 0.000 claims 1
- KPHTWLNCCIROCQ-UHFFFAOYSA-N 2-[2-(2-fluoro-4-methylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound FC1=CC(C)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O KPHTWLNCCIROCQ-UHFFFAOYSA-N 0.000 claims 1
- AGZAFCWQOAMYMA-UHFFFAOYSA-N 2-[2-(2-fluoro-5-methylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=CC=C(F)C(C=2C(=CC=C(C=2)C(F)(F)F)OCC(O)=O)=C1 AGZAFCWQOAMYMA-UHFFFAOYSA-N 0.000 claims 1
- CZRPYQXMJTVZCL-UHFFFAOYSA-N 2-[2-(2-fluoro-6-methylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=CC=CC(F)=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O CZRPYQXMJTVZCL-UHFFFAOYSA-N 0.000 claims 1
- NOCGXOCSBRTPOH-UHFFFAOYSA-N 2-[2-(2-fluorophenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=CC=C1F NOCGXOCSBRTPOH-UHFFFAOYSA-N 0.000 claims 1
- XKTKOCMSPJGZND-UHFFFAOYSA-N 2-[2-(2-methoxyphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound COC1=CC=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O XKTKOCMSPJGZND-UHFFFAOYSA-N 0.000 claims 1
- ARVXRFKSNMBAQY-UHFFFAOYSA-N 2-[2-(2-methyl-5-methylsulfonylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=CC=C(S(C)(=O)=O)C=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O ARVXRFKSNMBAQY-UHFFFAOYSA-N 0.000 claims 1
- GYUZBMREOWMBQM-UHFFFAOYSA-N 2-[2-(2-methyl-5-sulfamoylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O GYUZBMREOWMBQM-UHFFFAOYSA-N 0.000 claims 1
- JKGLEWXFVSHOTN-UHFFFAOYSA-N 2-[2-(2-methylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=CC=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O JKGLEWXFVSHOTN-UHFFFAOYSA-N 0.000 claims 1
- UUBPKAKFFTVBKJ-UHFFFAOYSA-N 2-[2-(2-nitrophenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=CC=C1[N+]([O-])=O UUBPKAKFFTVBKJ-UHFFFAOYSA-N 0.000 claims 1
- MCRYGBNSJLPWDC-UHFFFAOYSA-N 2-[2-(3,4-difluorophenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=C(F)C(F)=C1 MCRYGBNSJLPWDC-UHFFFAOYSA-N 0.000 claims 1
- GLSYUPIIWSOLAV-UHFFFAOYSA-N 2-[2-(3-chloro-2-methylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=C(Cl)C=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O GLSYUPIIWSOLAV-UHFFFAOYSA-N 0.000 claims 1
- YQPVFQSSUIRJBC-UHFFFAOYSA-N 2-[2-(3-cyanophenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=CC(C#N)=C1 YQPVFQSSUIRJBC-UHFFFAOYSA-N 0.000 claims 1
- RBCQYGNISLBEGG-UHFFFAOYSA-N 2-[2-(3-ethylsulfonylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CCS(=O)(=O)C1=CC=CC(C=2C(=CC=C(C=2)C(F)(F)F)OCC(O)=O)=C1 RBCQYGNISLBEGG-UHFFFAOYSA-N 0.000 claims 1
- AUTBLYGEKWAZEP-UHFFFAOYSA-N 2-[2-(3-fluoro-2,4-dimethylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=C(F)C(C)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O AUTBLYGEKWAZEP-UHFFFAOYSA-N 0.000 claims 1
- UTWFMLJSSASQLN-UHFFFAOYSA-N 2-[2-(3-fluoro-2-methylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=C(F)C=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O UTWFMLJSSASQLN-UHFFFAOYSA-N 0.000 claims 1
- MYYCKTHREXMOSE-UHFFFAOYSA-N 2-[2-(3-fluoro-4-phenylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=C(C=2C=CC=CC=2)C(F)=C1 MYYCKTHREXMOSE-UHFFFAOYSA-N 0.000 claims 1
- WRGYOKCBTYMNRQ-UHFFFAOYSA-N 2-[2-(3-fluorophenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=CC(F)=C1 WRGYOKCBTYMNRQ-UHFFFAOYSA-N 0.000 claims 1
- NTNLYYSHGOOZJP-UHFFFAOYSA-N 2-[2-(3-methoxyphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound COC1=CC=CC(C=2C(=CC=C(C=2)C(F)(F)F)OCC(O)=O)=C1 NTNLYYSHGOOZJP-UHFFFAOYSA-N 0.000 claims 1
- BIUAREGRQYRRGE-UHFFFAOYSA-N 2-[2-(3-methylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=CC=CC(C=2C(=CC=C(C=2)C(F)(F)F)OCC(O)=O)=C1 BIUAREGRQYRRGE-UHFFFAOYSA-N 0.000 claims 1
- HUCYOFYKRABGKI-UHFFFAOYSA-N 2-[2-(3-phenylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=CC(C=2C=CC=CC=2)=C1 HUCYOFYKRABGKI-UHFFFAOYSA-N 0.000 claims 1
- FDZVOMRKVVCYDG-UHFFFAOYSA-N 2-[2-(3-propan-2-ylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC(C)C1=CC=CC(C=2C(=CC=C(C=2)C(F)(F)F)OCC(O)=O)=C1 FDZVOMRKVVCYDG-UHFFFAOYSA-N 0.000 claims 1
- OJEAFCUSGJTYSF-UHFFFAOYSA-N 2-[2-(3-propoxyphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CCCOC1=CC=CC(C=2C(=CC=C(C=2)C(F)(F)F)OCC(O)=O)=C1 OJEAFCUSGJTYSF-UHFFFAOYSA-N 0.000 claims 1
- RSOBBGUVGICCMX-UHFFFAOYSA-N 2-[2-(4-acetylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound C1=CC(C(=O)C)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O RSOBBGUVGICCMX-UHFFFAOYSA-N 0.000 claims 1
- SCODQYQCZTWJOI-UHFFFAOYSA-N 2-[2-(4-amino-2-chlorophenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound ClC1=CC(N)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O SCODQYQCZTWJOI-UHFFFAOYSA-N 0.000 claims 1
- KOUGDDUBEWGVBY-UHFFFAOYSA-N 2-[2-(4-amino-2-methylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=CC(N)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O KOUGDDUBEWGVBY-UHFFFAOYSA-N 0.000 claims 1
- DVGJFVHFKUCXDH-UHFFFAOYSA-N 2-[2-(4-carbamoyl-2-methylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=CC(C(N)=O)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O DVGJFVHFKUCXDH-UHFFFAOYSA-N 0.000 claims 1
- GULJYUHSEUMMKX-UHFFFAOYSA-N 2-[2-(4-chloro-2-fluorophenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=C(Cl)C=C1F GULJYUHSEUMMKX-UHFFFAOYSA-N 0.000 claims 1
- KUOMSMSJYBWETF-UHFFFAOYSA-N 2-[2-(4-chloro-2-methylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=CC(Cl)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O KUOMSMSJYBWETF-UHFFFAOYSA-N 0.000 claims 1
- DIPRPJOBKLUDNB-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=C(Cl)C=C1 DIPRPJOBKLUDNB-UHFFFAOYSA-N 0.000 claims 1
- ZBTMWUJKAJEFTA-UHFFFAOYSA-N 2-[2-(4-cyano-2-methylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=CC(C#N)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O ZBTMWUJKAJEFTA-UHFFFAOYSA-N 0.000 claims 1
- MMMCNTGAJNCTHW-UHFFFAOYSA-N 2-[2-(4-cyanophenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=C(C#N)C=C1 MMMCNTGAJNCTHW-UHFFFAOYSA-N 0.000 claims 1
- CRSYCCHZQQRCAE-UHFFFAOYSA-N 2-[2-(4-ethylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound C1=CC(CC)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O CRSYCCHZQQRCAE-UHFFFAOYSA-N 0.000 claims 1
- BAEUVFVUAABNHC-UHFFFAOYSA-N 2-[2-(4-ethylsulfanylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound C1=CC(SCC)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O BAEUVFVUAABNHC-UHFFFAOYSA-N 0.000 claims 1
- KKRCWFMPEDXLBG-UHFFFAOYSA-N 2-[2-(4-ethylsulfonyl-2-fluorophenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound FC1=CC(S(=O)(=O)CC)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O KKRCWFMPEDXLBG-UHFFFAOYSA-N 0.000 claims 1
- FGIIAOOHNWYDFE-UHFFFAOYSA-N 2-[2-(4-ethylsulfonyl-2-methylphenyl)-4,5-difluorophenoxy]acetic acid Chemical compound CC1=CC(S(=O)(=O)CC)=CC=C1C1=CC(F)=C(F)C=C1OCC(O)=O FGIIAOOHNWYDFE-UHFFFAOYSA-N 0.000 claims 1
- ZDIAQFROROOGTE-UHFFFAOYSA-N 2-[2-(4-ethylsulfonyl-2-methylphenyl)-4,6-difluorophenoxy]acetic acid Chemical compound CC1=CC(S(=O)(=O)CC)=CC=C1C1=CC(F)=CC(F)=C1OCC(O)=O ZDIAQFROROOGTE-UHFFFAOYSA-N 0.000 claims 1
- PUFLNZXJKBHKDC-UHFFFAOYSA-N 2-[2-(4-ethylsulfonyl-2-methylphenyl)-4-(trifluoromethyl)phenoxy]-2-methylpropanoic acid Chemical compound CC1=CC(S(=O)(=O)CC)=CC=C1C1=CC(C(F)(F)F)=CC=C1OC(C)(C)C(O)=O PUFLNZXJKBHKDC-UHFFFAOYSA-N 0.000 claims 1
- KDOSMMYSHYZFQE-UHFFFAOYSA-N 2-[2-(4-ethylsulfonyl-2-methylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=CC(S(=O)(=O)CC)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O KDOSMMYSHYZFQE-UHFFFAOYSA-N 0.000 claims 1
- GCJIORHCPZEYFY-UHFFFAOYSA-N 2-[2-(4-ethylsulfonyl-2-methylphenyl)-4-(trifluoromethyl)phenoxy]butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=C(C(F)(F)F)C=C1C1=CC=C(S(=O)(=O)CC)C=C1C GCJIORHCPZEYFY-UHFFFAOYSA-N 0.000 claims 1
- QYSGYFIHQFOVNL-UHFFFAOYSA-N 2-[2-(4-ethylsulfonyl-2-methylphenyl)-4-fluorophenoxy]acetic acid Chemical compound CC1=CC(S(=O)(=O)CC)=CC=C1C1=CC(F)=CC=C1OCC(O)=O QYSGYFIHQFOVNL-UHFFFAOYSA-N 0.000 claims 1
- YMWRKLXZFIOALJ-UHFFFAOYSA-N 2-[2-(4-ethylsulfonylphenyl)-3-methyl-4-nitrophenoxy]acetic acid Chemical compound C1=CC(S(=O)(=O)CC)=CC=C1C1=C(C)C([N+]([O-])=O)=CC=C1OCC(O)=O YMWRKLXZFIOALJ-UHFFFAOYSA-N 0.000 claims 1
- MMJDGBUBTCBQDJ-UHFFFAOYSA-N 2-[2-(4-fluoro-2-methylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=CC(F)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O MMJDGBUBTCBQDJ-UHFFFAOYSA-N 0.000 claims 1
- PHPDEUQWPOBTAS-UHFFFAOYSA-N 2-[2-(4-fluorophenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=C(F)C=C1 PHPDEUQWPOBTAS-UHFFFAOYSA-N 0.000 claims 1
- ANMWINDRGQGGFO-UHFFFAOYSA-N 2-[2-(4-methoxy-2-methylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=CC(OC)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O ANMWINDRGQGGFO-UHFFFAOYSA-N 0.000 claims 1
- BAGKZNKMTKKDNL-UHFFFAOYSA-N 2-[2-(4-methoxyphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound C1=CC(OC)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O BAGKZNKMTKKDNL-UHFFFAOYSA-N 0.000 claims 1
- QDLWRCBHMLSQJJ-UHFFFAOYSA-N 2-[2-(4-methyl-2-pyrrolidin-1-ylpyrimidin-5-yl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical class CC1=NC(N2CCCC2)=NC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O QDLWRCBHMLSQJJ-UHFFFAOYSA-N 0.000 claims 1
- FFFLUOSGLPCFTD-UHFFFAOYSA-N 2-[2-(4-methylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O FFFLUOSGLPCFTD-UHFFFAOYSA-N 0.000 claims 1
- WHTYKOHLCWHQTF-UHFFFAOYSA-N 2-[2-(4-methylsulfanylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound C1=CC(SC)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O WHTYKOHLCWHQTF-UHFFFAOYSA-N 0.000 claims 1
- VMUQWDZAQHHYDS-UHFFFAOYSA-N 2-[2-(4-methylsulfonylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O VMUQWDZAQHHYDS-UHFFFAOYSA-N 0.000 claims 1
- ZEJULYNCPGLFIJ-UHFFFAOYSA-N 2-[2-(4-nitrophenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=C([N+]([O-])=O)C=C1 ZEJULYNCPGLFIJ-UHFFFAOYSA-N 0.000 claims 1
- QQSVTHQOIZCVPI-UHFFFAOYSA-N 2-[2-(4-phenylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=C(C=2C=CC=CC=2)C=C1 QQSVTHQOIZCVPI-UHFFFAOYSA-N 0.000 claims 1
- NKLVTKVKOCLLTC-UHFFFAOYSA-N 2-[2-(4-propoxyphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound C1=CC(OCCC)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O NKLVTKVKOCLLTC-UHFFFAOYSA-N 0.000 claims 1
- GHUDEUFPHWIEAW-UHFFFAOYSA-N 2-[2-(4-pyrrolidin-1-ylsulfonylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=C(S(=O)(=O)N2CCCC2)C=C1 GHUDEUFPHWIEAW-UHFFFAOYSA-N 0.000 claims 1
- YQYNPTBSUOSKJJ-UHFFFAOYSA-N 2-[2-(4-sulfamoylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O YQYNPTBSUOSKJJ-UHFFFAOYSA-N 0.000 claims 1
- USTPLZUEVJPAOK-UHFFFAOYSA-N 2-[2-(5-chloro-2-methylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=CC=C(Cl)C=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O USTPLZUEVJPAOK-UHFFFAOYSA-N 0.000 claims 1
- QZCCJJYAYCXVQE-UHFFFAOYSA-N 2-[2-(5-cyano-2-methoxyphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound COC1=CC=C(C#N)C=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O QZCCJJYAYCXVQE-UHFFFAOYSA-N 0.000 claims 1
- GVLJKSQNHNBZLD-UHFFFAOYSA-N 2-[2-(5-fluoro-2-methoxyphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound COC1=CC=C(F)C=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O GVLJKSQNHNBZLD-UHFFFAOYSA-N 0.000 claims 1
- KUDYEHATENWNQI-UHFFFAOYSA-N 2-[2-(5-fluoro-2-methylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=CC=C(F)C=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O KUDYEHATENWNQI-UHFFFAOYSA-N 0.000 claims 1
- DKPKWQHAPUIMRV-UHFFFAOYSA-N 2-[2-(6-methoxynaphthalen-2-yl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound C1=CC2=CC(OC)=CC=C2C=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O DKPKWQHAPUIMRV-UHFFFAOYSA-N 0.000 claims 1
- VHAZRWFMWGGLOQ-UHFFFAOYSA-N 2-[2-(carboxymethoxy)-5-(trifluoromethyl)phenyl]benzoic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=CC=C1C(O)=O VHAZRWFMWGGLOQ-UHFFFAOYSA-N 0.000 claims 1
- ADPZYLWZWQESCJ-UHFFFAOYSA-N 2-[2-[2-(3-hydroxyazetidin-1-yl)-4-methylpyrimidin-5-yl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical class CC1=NC(N2CC(O)C2)=NC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O ADPZYLWZWQESCJ-UHFFFAOYSA-N 0.000 claims 1
- GHQDVORWQCOBID-UHFFFAOYSA-N 2-[2-[2-(benzylamino)pyrimidin-5-yl]-4-chlorophenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1C(C=N1)=CN=C1NCC1=CC=CC=C1 GHQDVORWQCOBID-UHFFFAOYSA-N 0.000 claims 1
- BQGVWBRZFZKGGW-UHFFFAOYSA-N 2-[2-[2-(dimethylamino)-4-methylpyrimidin-5-yl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical class CC1=NC(N(C)C)=NC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O BQGVWBRZFZKGGW-UHFFFAOYSA-N 0.000 claims 1
- CDONMHDUEUHIHY-UHFFFAOYSA-N 2-[2-[2-(dimethylsulfamoylamino)-4-methylpyrimidin-5-yl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical class CC1=NC(NS(=O)(=O)N(C)C)=NC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O CDONMHDUEUHIHY-UHFFFAOYSA-N 0.000 claims 1
- HMXXWRJIYARKNH-UHFFFAOYSA-N 2-[2-[2-[acetyl(benzyl)amino]pyrimidin-5-yl]-4-chlorophenoxy]acetic acid Chemical compound N=1C=C(C=2C(=CC=C(Cl)C=2)OCC(O)=O)C=NC=1N(C(=O)C)CC1=CC=CC=C1 HMXXWRJIYARKNH-UHFFFAOYSA-N 0.000 claims 1
- RWLYACBVYQZDRY-UHFFFAOYSA-N 2-[2-[2-[benzyl(ethylsulfonyl)amino]pyrimidin-5-yl]-4-chlorophenoxy]acetic acid Chemical compound N=1C=C(C=2C(=CC=C(Cl)C=2)OCC(O)=O)C=NC=1N(S(=O)(=O)CC)CC1=CC=CC=C1 RWLYACBVYQZDRY-UHFFFAOYSA-N 0.000 claims 1
- MOZXRNUYFZBRMH-UHFFFAOYSA-N 2-[2-[2-[benzyl(methylsulfonyl)amino]pyrimidin-5-yl]-4-chlorophenoxy]acetic acid Chemical compound N=1C=C(C=2C(=CC=C(Cl)C=2)OCC(O)=O)C=NC=1N(S(=O)(=O)C)CC1=CC=CC=C1 MOZXRNUYFZBRMH-UHFFFAOYSA-N 0.000 claims 1
- PFXDIMQUORBMIW-UHFFFAOYSA-N 2-[2-[2-chloro-4-(methoxycarbonylamino)phenyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical class ClC1=CC(NC(=O)OC)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O PFXDIMQUORBMIW-UHFFFAOYSA-N 0.000 claims 1
- HPOGFARAIVTDNZ-UHFFFAOYSA-N 2-[2-[2-methyl-4-(methylcarbamoylamino)phenyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=CC(NC(=O)NC)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O HPOGFARAIVTDNZ-UHFFFAOYSA-N 0.000 claims 1
- NGEKZOBZIIFXHG-UHFFFAOYSA-N 2-[2-[2-methyl-4-(propylcarbamoylamino)phenyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=CC(NC(=O)NCCC)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O NGEKZOBZIIFXHG-UHFFFAOYSA-N 0.000 claims 1
- GMRGXCVUEIAYOU-UHFFFAOYSA-N 2-[2-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC=C(C=2C(=CC=C(C=2)C(F)(F)F)OCC(O)=O)C=C1 GMRGXCVUEIAYOU-UHFFFAOYSA-N 0.000 claims 1
- PRKBZOPLGFNBAV-UHFFFAOYSA-N 2-[2-[4-(benzylsulfamoyl)phenyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=C(S(=O)(=O)NCC=2C=CC=CC=2)C=C1 PRKBZOPLGFNBAV-UHFFFAOYSA-N 0.000 claims 1
- LIGKBEYTORUBMT-UHFFFAOYSA-N 2-[2-[4-(cyclopropylcarbamoylamino)-2-methylphenyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound C=1C=C(C=2C(=CC=C(C=2)C(F)(F)F)OCC(O)=O)C(C)=CC=1NC(=O)NC1CC1 LIGKBEYTORUBMT-UHFFFAOYSA-N 0.000 claims 1
- CIAPJPXVLYXLOB-UHFFFAOYSA-N 2-[2-[4-(cyclopropylsulfamoyl)phenyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=C(S(=O)(=O)NC2CC2)C=C1 CIAPJPXVLYXLOB-UHFFFAOYSA-N 0.000 claims 1
- AJOOJNSIVXELDW-UHFFFAOYSA-N 2-[2-[4-(diethylsulfamoyl)phenyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound C1=CC(S(=O)(=O)N(CC)CC)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O AJOOJNSIVXELDW-UHFFFAOYSA-N 0.000 claims 1
- OANKMNXZOGOYMB-UHFFFAOYSA-N 2-[2-[4-(dimethylsulfamoyl)phenyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O OANKMNXZOGOYMB-UHFFFAOYSA-N 0.000 claims 1
- YCMGCJFATYIZQM-UHFFFAOYSA-N 2-[2-[4-(ethylcarbamoylamino)-2-methylphenyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=CC(NC(=O)NCC)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O YCMGCJFATYIZQM-UHFFFAOYSA-N 0.000 claims 1
- DQPFWLDCGJVBBT-UHFFFAOYSA-N 2-[2-[4-(methylsulfamoyl)phenyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O DQPFWLDCGJVBBT-UHFFFAOYSA-N 0.000 claims 1
- UNAVKCWSILQPIL-UHFFFAOYSA-N 2-[2-[4-(phenylsulfamoyl)phenyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=C(S(=O)(=O)NC=2C=CC=CC=2)C=C1 UNAVKCWSILQPIL-UHFFFAOYSA-N 0.000 claims 1
- QDRHXWFWVUXZGP-UHFFFAOYSA-N 2-[2-[4-(trifluoromethoxy)phenyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=C(OC(F)(F)F)C=C1 QDRHXWFWVUXZGP-UHFFFAOYSA-N 0.000 claims 1
- PSWXZHGXDFCOSA-UHFFFAOYSA-N 2-[2-[4-[(5-methyl-1,3-thiazol-2-yl)sulfamoyl]phenyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound S1C(C)=CN=C1NS(=O)(=O)C1=CC=C(C=2C(=CC=C(C=2)C(F)(F)F)OCC(O)=O)C=C1 PSWXZHGXDFCOSA-UHFFFAOYSA-N 0.000 claims 1
- YSLZKBHEGZCEHQ-UHFFFAOYSA-N 2-[2-[4-methyl-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical class C1CN(C)CCN1C1=NC=C(C=2C(=CC=C(C=2)C(F)(F)F)OCC(O)=O)C(C)=N1 YSLZKBHEGZCEHQ-UHFFFAOYSA-N 0.000 claims 1
- ARHHSLIBEBKDKV-UHFFFAOYSA-N 2-[2-[4-methyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=NC(N(C)S(C)(=O)=O)=NC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O ARHHSLIBEBKDKV-UHFFFAOYSA-N 0.000 claims 1
- MVWUOTAYDROAOL-UHFFFAOYSA-N 2-[2-[4-methyl-6-[methyl(methylsulfonyl)amino]pyridin-3-yl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound C1=NC(N(C)S(C)(=O)=O)=CC(C)=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O MVWUOTAYDROAOL-UHFFFAOYSA-N 0.000 claims 1
- JUAOESKHXKLGQM-UHFFFAOYSA-N 2-[2-[4-methylsulfonyl-2-(trifluoromethyl)phenyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound FC(F)(F)C1=CC(S(=O)(=O)C)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O JUAOESKHXKLGQM-UHFFFAOYSA-N 0.000 claims 1
- JBYIDESLXQQPLX-UHFFFAOYSA-N 2-[2-[5-methyl-2-[methyl(methylsulfonyl)amino]pyrimidin-4-yl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical class CS(=O)(=O)N(C)C1=NC=C(C)C(C=2C(=CC=C(C=2)C(F)(F)F)OCC(O)=O)=N1 JBYIDESLXQQPLX-UHFFFAOYSA-N 0.000 claims 1
- FHDNJPNYTQSYKW-UHFFFAOYSA-N 2-[2-naphthalen-2-yl-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=C(C=CC=C2)C2=C1 FHDNJPNYTQSYKW-UHFFFAOYSA-N 0.000 claims 1
- RYVXTJPPKQDBGU-UHFFFAOYSA-N 2-[2-pyridin-3-yl-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=CN=C1 RYVXTJPPKQDBGU-UHFFFAOYSA-N 0.000 claims 1
- XCCVYEJDWRXGTG-UHFFFAOYSA-N 2-[2-quinolin-8-yl-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=CC2=CC=CN=C12 XCCVYEJDWRXGTG-UHFFFAOYSA-N 0.000 claims 1
- DRNAANNKSLRCDH-UHFFFAOYSA-N 2-[4-(trifluoromethyl)-2-[2-(trifluoromethyl)phenyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=CC=C1C(F)(F)F DRNAANNKSLRCDH-UHFFFAOYSA-N 0.000 claims 1
- UXQQMMDXZWYPBJ-UHFFFAOYSA-N 2-[4-(trifluoromethyl)-2-[3-(trifluoromethylsulfanyl)phenyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=CC(SC(F)(F)F)=C1 UXQQMMDXZWYPBJ-UHFFFAOYSA-N 0.000 claims 1
- FSKULNUBHRBBGE-UHFFFAOYSA-N 2-[4-(trifluoromethyl)-2-[4-(trifluoromethyl)phenyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=C(C(F)(F)F)C=C1 FSKULNUBHRBBGE-UHFFFAOYSA-N 0.000 claims 1
- ZAKWIDLWLJSHAX-UHFFFAOYSA-N 2-[4-(trifluoromethyl)-2-[4-(trifluoromethylsulfanyl)phenyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=C(SC(F)(F)F)C=C1 ZAKWIDLWLJSHAX-UHFFFAOYSA-N 0.000 claims 1
- CNMBRSATMDIDOG-UHFFFAOYSA-N 2-[4-chloro-2-(2-chloro-4-ethylsulfonylphenyl)phenoxy]acetic acid Chemical compound ClC1=CC(S(=O)(=O)CC)=CC=C1C1=CC(Cl)=CC=C1OCC(O)=O CNMBRSATMDIDOG-UHFFFAOYSA-N 0.000 claims 1
- QRRGBYUQOHJQJK-UHFFFAOYSA-N 2-[4-chloro-2-(2-morpholin-4-ylpyrimidin-5-yl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1C1=CN=C(N2CCOCC2)N=C1 QRRGBYUQOHJQJK-UHFFFAOYSA-N 0.000 claims 1
- RGODETFFIUHCPB-UHFFFAOYSA-N 2-[4-chloro-2-(2-piperidin-1-ylpyrimidin-5-yl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1C1=CN=C(N2CCCCC2)N=C1 RGODETFFIUHCPB-UHFFFAOYSA-N 0.000 claims 1
- ZCFFMTCERKTYFB-UHFFFAOYSA-N 2-[4-chloro-2-(3,4-dimethoxyphenyl)phenoxy]acetic acid Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(Cl)=CC=C1OCC(O)=O ZCFFMTCERKTYFB-UHFFFAOYSA-N 0.000 claims 1
- LKVOYKPVSRJIAP-UHFFFAOYSA-N 2-[4-chloro-2-(3-cyanophenyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1C1=CC=CC(C#N)=C1 LKVOYKPVSRJIAP-UHFFFAOYSA-N 0.000 claims 1
- MMVMFRJPPGRYKS-UHFFFAOYSA-N 2-[4-chloro-2-(4-chlorophenyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1C1=CC=C(Cl)C=C1 MMVMFRJPPGRYKS-UHFFFAOYSA-N 0.000 claims 1
- JUKQBUGEOLGQHR-UHFFFAOYSA-N 2-[4-chloro-2-(4-cyanophenyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1C1=CC=C(C#N)C=C1 JUKQBUGEOLGQHR-UHFFFAOYSA-N 0.000 claims 1
- XEOTZAFNMGKWMV-UHFFFAOYSA-N 2-[4-chloro-2-(4-ethylsulfanylphenyl)phenoxy]acetic acid Chemical compound C1=CC(SCC)=CC=C1C1=CC(Cl)=CC=C1OCC(O)=O XEOTZAFNMGKWMV-UHFFFAOYSA-N 0.000 claims 1
- MNOSYFBXUCZGCA-UHFFFAOYSA-N 2-[4-chloro-2-(4-ethylsulfonyl-2-fluorophenyl)phenoxy]acetic acid Chemical compound FC1=CC(S(=O)(=O)CC)=CC=C1C1=CC(Cl)=CC=C1OCC(O)=O MNOSYFBXUCZGCA-UHFFFAOYSA-N 0.000 claims 1
- LTELLSHJEKDTRM-UHFFFAOYSA-N 2-[4-chloro-2-(4-ethylsulfonyl-2-methylphenyl)phenoxy]acetic acid Chemical compound CC1=CC(S(=O)(=O)CC)=CC=C1C1=CC(Cl)=CC=C1OCC(O)=O LTELLSHJEKDTRM-UHFFFAOYSA-N 0.000 claims 1
- YRVWJRVZOAQHTC-UHFFFAOYSA-N 2-[4-chloro-2-(4-ethylsulfonylphenyl)-3-methylphenoxy]acetic acid Chemical compound C1=CC(S(=O)(=O)CC)=CC=C1C1=C(C)C(Cl)=CC=C1OCC(O)=O YRVWJRVZOAQHTC-UHFFFAOYSA-N 0.000 claims 1
- MREHKHMPXVGCAP-UHFFFAOYSA-N 2-[4-chloro-2-(4-ethylsulfonylphenyl)phenoxy]acetic acid Chemical compound C1=CC(S(=O)(=O)CC)=CC=C1C1=CC(Cl)=CC=C1OCC(O)=O MREHKHMPXVGCAP-UHFFFAOYSA-N 0.000 claims 1
- GEVIBUAPNOFYBW-UHFFFAOYSA-N 2-[4-chloro-2-(4-ethylsulfonylphenyl)phenoxy]propanoic acid Chemical compound C1=CC(S(=O)(=O)CC)=CC=C1C1=CC(Cl)=CC=C1OC(C)C(O)=O GEVIBUAPNOFYBW-UHFFFAOYSA-N 0.000 claims 1
- VRRDLQCATXLPSY-UHFFFAOYSA-N 2-[4-chloro-2-(4-methoxyphenyl)phenoxy]acetic acid Chemical compound C1=CC(OC)=CC=C1C1=CC(Cl)=CC=C1OCC(O)=O VRRDLQCATXLPSY-UHFFFAOYSA-N 0.000 claims 1
- PVQZLNPEACVEOJ-UHFFFAOYSA-N 2-[4-chloro-2-(4-methyl-2-morpholin-4-ylpyrimidin-5-yl)phenoxy]acetic acid Chemical compound CC1=NC(N2CCOCC2)=NC=C1C1=CC(Cl)=CC=C1OCC(O)=O PVQZLNPEACVEOJ-UHFFFAOYSA-N 0.000 claims 1
- HFTNPRKIHDBKQL-UHFFFAOYSA-N 2-[4-chloro-2-(4-methylsulfonylphenyl)phenoxy]acetic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC(Cl)=CC=C1OCC(O)=O HFTNPRKIHDBKQL-UHFFFAOYSA-N 0.000 claims 1
- WXRFORXMBFHLNA-UHFFFAOYSA-N 2-[4-chloro-2-(5-sulfamoylpyridin-2-yl)phenoxy]acetic acid Chemical compound N1=CC(S(=O)(=O)N)=CC=C1C1=CC(Cl)=CC=C1OCC(O)=O WXRFORXMBFHLNA-UHFFFAOYSA-N 0.000 claims 1
- HBKROLVJGLUKMO-UHFFFAOYSA-N 2-[4-chloro-2-[2-(dimethylamino)pyrimidin-5-yl]phenoxy]acetic acid Chemical compound C1=NC(N(C)C)=NC=C1C1=CC(Cl)=CC=C1OCC(O)=O HBKROLVJGLUKMO-UHFFFAOYSA-N 0.000 claims 1
- SPVSATLUZHWGPD-UHFFFAOYSA-N 2-[4-chloro-2-[2-(methylamino)pyrimidin-5-yl]phenoxy]acetic acid Chemical compound C1=NC(NC)=NC=C1C1=CC(Cl)=CC=C1OCC(O)=O SPVSATLUZHWGPD-UHFFFAOYSA-N 0.000 claims 1
- TUNVNOMUIZAZHD-UHFFFAOYSA-N 2-[4-chloro-2-[2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl]phenoxy]acetic acid Chemical compound C1=NC(N(C)S(C)(=O)=O)=NC=C1C1=CC(Cl)=CC=C1OCC(O)=O TUNVNOMUIZAZHD-UHFFFAOYSA-N 0.000 claims 1
- PZPVQKKTULQJKR-UHFFFAOYSA-N 2-[4-chloro-2-[4-ethylsulfonyl-2-(trifluoromethyl)phenyl]phenoxy]acetic acid Chemical compound FC(F)(F)C1=CC(S(=O)(=O)CC)=CC=C1C1=CC(Cl)=CC=C1OCC(O)=O PZPVQKKTULQJKR-UHFFFAOYSA-N 0.000 claims 1
- HTIWEICBKFSCKK-UHFFFAOYSA-N 3-[2-(carboxymethoxy)-5-(trifluoromethyl)phenyl]benzoic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=CC(C(O)=O)=C1 HTIWEICBKFSCKK-UHFFFAOYSA-N 0.000 claims 1
- SIHNZQIPHJIVEM-UHFFFAOYSA-N 4-[2-(carboxymethoxy)-5-(trifluoromethyl)phenyl]benzoic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C1=CC=C(C(O)=O)C=C1 SIHNZQIPHJIVEM-UHFFFAOYSA-N 0.000 claims 1
- JPOYSNBDUKQLRR-UHFFFAOYSA-N 4-[2-(carboxymethoxy)-5-chlorophenyl]benzoic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1C1=CC=C(C(O)=O)C=C1 JPOYSNBDUKQLRR-UHFFFAOYSA-N 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- BHMBVRSPMRCCGG-OUTUXVNYSA-N prostaglandin D2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O BHMBVRSPMRCCGG-OUTUXVNYSA-N 0.000 claims 1
- BHMBVRSPMRCCGG-UHFFFAOYSA-N prostaglandine D2 Natural products CCCCCC(O)C=CC1C(CC=CCCCC(O)=O)C(O)CC1=O BHMBVRSPMRCCGG-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000005493 quinolyl group Chemical group 0.000 claims 1
- 206010039083 rhinitis Diseases 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
- 0 *C(C(O)=O)(N)Oc1ccc(*)cc1N Chemical compound *C(C(O)=O)(N)Oc1ccc(*)cc1N 0.000 description 1
- HLHNOIAOWQFNGW-UHFFFAOYSA-N 3-bromo-4-hydroxybenzonitrile Chemical compound OC1=CC=C(C#N)C=C1Br HLHNOIAOWQFNGW-UHFFFAOYSA-N 0.000 description 1
- DCIPFSYBGTWYCR-UHFFFAOYSA-N 5847-59-6 Chemical compound OC1=CC=C([N+]([O-])=O)C=C1Br DCIPFSYBGTWYCR-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0301010A SE0301010D0 (sv) | 2003-04-07 | 2003-04-07 | Novel compounds |
| SE0301010-5 | 2003-04-07 | ||
| PCT/SE2004/000535 WO2004089885A1 (en) | 2003-04-07 | 2004-04-06 | Novel compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006522118A JP2006522118A (ja) | 2006-09-28 |
| JP2006522118A5 true JP2006522118A5 (enExample) | 2009-06-04 |
| JP4898428B2 JP4898428B2 (ja) | 2012-03-14 |
Family
ID=20290949
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006508007A Expired - Fee Related JP4898428B2 (ja) | 2003-04-07 | 2004-04-06 | 新規化合物 |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US8158820B2 (enExample) |
| EP (1) | EP1611091B1 (enExample) |
| JP (1) | JP4898428B2 (enExample) |
| KR (1) | KR101061339B1 (enExample) |
| CN (1) | CN100575330C (enExample) |
| AR (1) | AR043998A1 (enExample) |
| AU (1) | AU2004228599B2 (enExample) |
| BR (1) | BRPI0409109A (enExample) |
| CA (1) | CA2521425C (enExample) |
| CO (1) | CO5640047A2 (enExample) |
| CY (1) | CY1115940T1 (enExample) |
| DK (1) | DK1611091T3 (enExample) |
| ES (1) | ES2525763T3 (enExample) |
| IS (1) | IS8108A (enExample) |
| MX (1) | MXPA05010682A (enExample) |
| MY (1) | MY149463A (enExample) |
| NO (1) | NO20055219L (enExample) |
| NZ (1) | NZ542972A (enExample) |
| PL (1) | PL1611091T3 (enExample) |
| PT (1) | PT1611091E (enExample) |
| RU (1) | RU2372330C2 (enExample) |
| SE (1) | SE0301010D0 (enExample) |
| SI (1) | SI1611091T1 (enExample) |
| TW (1) | TWI336322B (enExample) |
| WO (1) | WO2004089885A1 (enExample) |
| ZA (1) | ZA200508088B (enExample) |
Families Citing this family (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE0301009D0 (sv) * | 2003-04-07 | 2003-04-07 | Astrazeneca Ab | Novel compounds |
| SE0301010D0 (sv) | 2003-04-07 | 2003-04-07 | Astrazeneca Ab | Novel compounds |
| SA04250253B1 (ar) | 2003-08-21 | 2009-11-10 | استرازينيكا ايه بي | احماض فينوكسي اسيتيك مستبدلة باعتبارها مركبات صيدلانية لعلاج الامراض التنفسية مثل الربو ومرض الانسداد الرئوي المزمن |
| RU2387652C2 (ru) | 2004-03-11 | 2010-04-27 | Актелион Фармасьютиклз Лтд | Производные тетрагидропиридоиндола |
| GB0409921D0 (en) * | 2004-05-04 | 2004-06-09 | Novartis Ag | Organic compounds |
| US8022063B2 (en) * | 2004-05-29 | 2011-09-20 | 7Tm Pharma A/S | CRTH2 receptor ligands for medicinal uses |
| WO2005115374A1 (en) * | 2004-05-29 | 2005-12-08 | 7Tm Pharma A/S | Crth2 receptor ligands for therapeutic use |
| GB0415320D0 (en) | 2004-07-08 | 2004-08-11 | Astrazeneca Ab | Novel compounds |
| GB0418830D0 (en) | 2004-08-24 | 2004-09-22 | Astrazeneca Ab | Novel compounds |
| GB0422057D0 (en) * | 2004-10-05 | 2004-11-03 | Astrazeneca Ab | Novel compounds |
| JP5208510B2 (ja) * | 2004-11-23 | 2013-06-12 | アストラゼネカ・アクチエボラーグ | 呼吸器疾患の処置に有用なフェノキシ酢酸誘導体 |
| GB0427381D0 (en) * | 2004-12-14 | 2005-01-19 | Novartis Ag | Organic compounds |
| GB0510584D0 (en) * | 2005-05-24 | 2005-06-29 | Novartis Ag | Organic compounds |
| GB0510585D0 (en) * | 2005-05-24 | 2005-06-29 | Novartis Ag | Organic compounds |
| KR101289995B1 (ko) | 2005-09-27 | 2013-07-26 | 시오노기 앤드 컴파니, 리미티드 | Ｐｇｄ2 수용체 길항제 활성을 갖는 설폰아마이드 유도체 |
| EA015358B1 (ru) * | 2005-09-30 | 2011-06-30 | Пульмаджен Терапьютикс (Эсме) Лимитед | Хинолины и их терапевтическое применение |
| TW200745003A (en) * | 2005-10-06 | 2007-12-16 | Astrazeneca Ab | Novel compounds |
| JP5155171B2 (ja) | 2005-10-06 | 2013-02-27 | アストラゼネカ・アクチエボラーグ | 新規化合物 |
| GB0520324D0 (en) * | 2005-10-06 | 2005-11-16 | Astrazeneca Ab | Novel compounds |
| RU2424229C2 (ru) * | 2005-10-06 | 2011-07-20 | Астразенека Аб | Производные бифенилоксиуксусной кислоты, их применение для изготовления лекарственного средства и промежуточные соединения |
| US20080255150A1 (en) * | 2005-11-05 | 2008-10-16 | Astrazeneca Ab | Novel Compounds |
| GB0524428D0 (en) | 2005-11-30 | 2006-01-11 | 7Tm Pharma As | Medicinal use of receptor ligands |
| EP1963259B1 (en) * | 2005-12-15 | 2012-02-15 | AstraZeneca AB | Substituted diphenylethers, -amines, -sulfides and -methanes for the treatment of respiratory disease |
| JP2009528273A (ja) * | 2006-01-25 | 2009-08-06 | シンタ ファーマシューティカルズ コーポレーション | 炎症および免疫関連使用用の置換ビアリール化合物 |
| AU2007208239B2 (en) | 2006-01-25 | 2013-04-18 | Synta Pharmaceuticals Corp. | Substituted aromatic compounds for inflammation and immune-related uses |
| GB0611695D0 (en) * | 2006-06-13 | 2006-07-26 | Novartis Ag | Organic compounds |
| PE20090213A1 (es) | 2007-05-04 | 2009-02-28 | Bristol Myers Squibb Co | Agonistas del receptor acoplado a la proteina g gpr119 [6,5]-biciclicos |
| WO2008137435A1 (en) | 2007-05-04 | 2008-11-13 | Bristol-Myers Squibb Company | [6,6] and [6,7]-bicyclic gpr119 g protein-coupled receptor agonists |
| UA100983C2 (ru) | 2007-07-05 | 2013-02-25 | Астразенека Аб | Бифенилоксипропановая кислота как модулятор crth2 и интермедиаты |
| EA018709B1 (ru) | 2007-07-17 | 2013-10-30 | Бристол-Маерс Сквибб Компани | Пиридоновые агонисты сопряженного с g-белком рецептора gpr119 |
| WO2009013348A2 (en) * | 2007-07-26 | 2009-01-29 | Novartis Ag | Pyrimidine derivatives useful for the treatment of inflammatory or allergic conditions |
| JP2010536839A (ja) * | 2007-08-17 | 2010-12-02 | アストラゼネカ アクチボラグ | 化合物９７９ |
| CA2707785C (en) | 2007-12-14 | 2015-11-03 | Pulmagen Therapeutics (Asthma) Limited | Indoles and their therapeutic use |
| WO2009089192A1 (en) * | 2008-01-07 | 2009-07-16 | Ligand Pharmaceuticals Inc. | 2-phenyl phenoxyacetic acids useful for treating inflammatory disorders |
| WO2009151910A2 (en) * | 2008-05-25 | 2009-12-17 | Wyeth | Combination product of receptor tyrosine kinase inhibitor and fatty acid synthase inhibitor for treating cancer |
| TW201006821A (en) | 2008-07-16 | 2010-02-16 | Bristol Myers Squibb Co | Pyridone and pyridazone analogues as GPR119 modulators |
| GB0913345D0 (en) | 2009-07-31 | 2009-09-16 | Astrazeneca Ab | New combination 802 |
| WO2011061527A1 (en) | 2009-11-17 | 2011-05-26 | Astrazeneca Ab | Combinations comprising a glucocorticoid receptor modulator for the treatment of respiratory diseases |
| MX2012011460A (es) | 2010-04-08 | 2012-11-23 | Squibb Bristol Myers Co | Analogos de pirimidinilpiperidiniloxipiridinona como moduladores de gpr119. |
| JP5800898B2 (ja) | 2010-07-05 | 2015-10-28 | アクテリオン ファーマシューティカルズ リミテッドＡｃｔｅｌｉｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｌｔｄ | １−フェニル−置換ヘテロシクリル誘導体及びプロスタグランジンｄ２受容体調節剤としてのそれらの使用 |
| EP2457900A1 (en) | 2010-11-25 | 2012-05-30 | Almirall, S.A. | New pyrazole derivatives having CRTh2 antagonistic behaviour |
| GB201021992D0 (en) | 2010-12-23 | 2011-02-02 | Astrazeneca Ab | Compound |
| GB201021979D0 (en) | 2010-12-23 | 2011-02-02 | Astrazeneca Ab | New compound |
| TWI550071B (zh) | 2011-03-25 | 2016-09-21 | 捷恩智股份有限公司 | 原酸酯化合物、液晶組成物及液晶顯示元件 |
| CN102408286B (zh) * | 2011-09-14 | 2013-11-13 | 浙江工业大学 | 一种n,n-二取代磺酰胺类化合物的制备方法 |
| SG11201402796SA (en) | 2011-12-16 | 2014-06-27 | Atopix Therapeutics Ltd | Combination of crth2 antagonist and a proton pump inhibitor for the treatment of eosinophilic esophagitis |
| RU2014129613A (ru) | 2011-12-21 | 2016-02-10 | Актелион Фармасьютиклз Лтд | Гетероциклильные производные и их применение в качестве модуляторов рецептора простагландина d2 |
| US9169270B2 (en) | 2012-07-05 | 2015-10-27 | Actelion Pharmaceuticals Ltd. | 1-phenyl-substituted heterocyclyl derivatives and their use as prostaglandin D2 receptor modulators |
| ES2784489T3 (es) | 2013-06-27 | 2020-09-28 | Lg Chemical Ltd | Derivados de biarilo como agonistas de GPR120 |
| JP2015051936A (ja) * | 2013-09-06 | 2015-03-19 | 株式会社日本触媒 | ホウ素化合物の製造方法 |
| US9630935B2 (en) * | 2013-09-17 | 2017-04-25 | Vectus Biosystems Limited | Compositions for the treatment of hypertension and/or fibrosis |
| US9783522B2 (en) | 2014-04-24 | 2017-10-10 | Mitsubishi Tanabe Pharma Corporation | 2-amino-pyridine and 2-amino-pyrimidine derivatives and medicinal use thereof |
| CN105439946B (zh) * | 2014-08-13 | 2018-02-02 | 益方生物科技（上海）有限公司 | 羧酸化合物及其制备方法和用途 |
| CA2970011C (en) | 2014-12-24 | 2021-08-03 | Lg Chem, Ltd. | Biaryl derivative as gpr120 agonist |
| DK3307262T3 (da) | 2015-06-15 | 2021-08-09 | Nmd Pharma As | Forbindelser til anvendelse ved behandling af neuromuskulære lidelser |
| US11730714B2 (en) | 2017-12-14 | 2023-08-22 | Nmd Pharma A/S | Compounds for the treatment of neuromuscular disorders |
| US11147788B2 (en) | 2017-12-14 | 2021-10-19 | Nmd Pharma A/S | Compounds for the treatment of neuromuscular disorders |
| US11591284B2 (en) | 2017-12-14 | 2023-02-28 | Nmd Pharma A/S | Compounds for the treatment of neuromuscular disorders |
| US10385028B2 (en) | 2017-12-14 | 2019-08-20 | Nmd Pharma A/S | Compounds for the treatment of neuromuscular disorders |
| US12440477B2 (en) | 2017-12-14 | 2025-10-14 | Nmd Pharma A/S | Compounds for the treatment of neuromuscular disorders |
| TWI780281B (zh) * | 2017-12-14 | 2022-10-11 | 丹麥商Ｎｍｄ藥品公司 | 用於治療神經肌肉病症的化合物 |
| KR102900834B1 (ko) * | 2019-06-19 | 2025-12-16 | 엔엠디 파마 에이/에스 | Clc-1 클로라이드 채널 억제제의 제조 방법 |
| CN117142949B (zh) * | 2023-08-31 | 2026-03-17 | 上海应用技术大学 | 一种联苯类3cl蛋白酶抑制剂及其制备方法与应用 |
Family Cites Families (77)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB690816A (en) | 1950-01-02 | 1953-04-29 | British Drug Houses Ltd | Improvements in or relating to the manufacture of substituted phenoxy acetic acids |
| US3278524A (en) | 1962-03-13 | 1966-10-11 | Beecham Group Ltd | Penicillins and their production |
| CH432119A (de) | 1963-02-22 | 1967-03-15 | Geigy Ag J R | Verwendung von Halogen-o-hydroxy-diphenyläthern als antimikrobielle Mittel |
| BE790679A (fr) * | 1971-11-03 | 1973-04-27 | Ici Ltd | Derives de l'indole |
| DD113545A5 (enExample) | 1973-03-30 | 1975-06-12 | ||
| JPS5239888B2 (enExample) | 1973-05-28 | 1977-10-07 | ||
| CA1041531A (en) | 1973-10-29 | 1978-10-31 | Eisai Co. Ltd. | M-phenoxyphenyl propionic acid derivatives and preparation thereof |
| CH582476A5 (enExample) | 1973-10-29 | 1976-12-15 | Ciba Geigy Ag | |
| GB1585963A (en) | 1976-10-14 | 1981-03-11 | Lilly Industries Ltd | Aryl sulphur compounds |
| US4248618A (en) | 1977-05-06 | 1981-02-03 | Ici Australia Limited | Derivatives of (pyrimidyloxy)phenoxy-alkanecarboxylic acid and herbicidal compositions thereof |
| FR2428629A1 (fr) | 1978-06-14 | 1980-01-11 | Hexachimie | Nouveaux composes bis(aryloxycarboxyliques), leur preparation et leur utilisation en therapeutique |
| JPS5951943B2 (ja) | 1978-08-21 | 1984-12-17 | キツセイ薬品工業株式会社 | 新規なイミダゾ−ル誘導体 |
| GB2041363B (en) | 1979-01-19 | 1982-10-06 | Pfizer Ltd | N-benzyl-imidazoles |
| US4670566A (en) | 1979-07-12 | 1987-06-02 | A. H. Robins Company, Incorporated | 3-methyl-hio-4-(5-, 6-, or 7-)phenylindolindolin-2-ones |
| US4486593A (en) | 1983-01-19 | 1984-12-04 | The Upjohn Company | 2-,3-, or 4-Pyridinylmethylamino arylic acids as thromboxane A2 synthetase and 5-lipoxygenase inhibitors |
| US5006542A (en) | 1988-10-31 | 1991-04-09 | E. R. Squibb & Sons, Inc. | Arylthioalkylphenyl carboxylic acids, derivatives thereof, compositions containing same and method of use |
| US5145790A (en) | 1990-05-04 | 1992-09-08 | Abbott Laboratories | Reagents and method for detecting polychlorinated biphenyls |
| NL9001752A (nl) * | 1990-08-02 | 1992-03-02 | Cedona Pharm Bv | Nieuwe 1,4-dihydropyridinederivaten. |
| EP0540165A1 (en) | 1991-10-03 | 1993-05-05 | Zeneca Limited | Alkanoic acid derivatives |
| WO1993012086A1 (fr) | 1991-12-11 | 1993-06-24 | Ss Pharmaceutical Co., Ltd. | Derive d'arylamide |
| CA2090283A1 (en) | 1992-02-28 | 1993-08-29 | Nobuyuki Hamanaka | Phenoxyacetic acid derivatives |
| DE69329894T2 (de) | 1992-12-08 | 2001-05-03 | Ss Pharmaceutical Co., Ltd. | Arylamidderivate |
| JPH06313995A (ja) * | 1993-04-28 | 1994-11-08 | Hodogaya Chem Co Ltd | 静電荷像現像用トナー |
| DE69411803T2 (de) | 1993-04-30 | 1998-12-03 | Kabushiki Kaisha Meidensha, Tokio/Tokyo | Elektrode und Verfahren zur Herstellung eines Elektrodenmaterials |
| JPH07140725A (ja) * | 1993-06-25 | 1995-06-02 | Hodogaya Chem Co Ltd | 負帯電性トナー用摩擦帯電付与部材 |
| EE9600184A (et) * | 1994-06-27 | 1997-06-16 | Cytomed, Inc. | Kardiovaskulaar-, inflammatoor- ja immuunhaiguste raviühendid ja -meetodid |
| NZ313896A (en) | 1995-08-28 | 2000-08-25 | American Home Prod | 4-formyl-2-(naphthalenylmethyl)phenoxyacetic acids or salts and antihyperglycemic agents for the treatment of diabetes mellitus |
| PT939628E (pt) | 1996-07-22 | 2003-07-31 | Monsanto Co | Inibidores tiolsulfona de metaloproteases |
| CA2219269A1 (en) * | 1996-10-29 | 1998-04-29 | Novartis Ag | Novel herbicides |
| FR2763588B1 (fr) | 1997-05-23 | 1999-07-09 | Cird Galderma | Composes triaromatiques, compositions les contenant et utilisations |
| GB9714249D0 (en) | 1997-07-08 | 1997-09-10 | Angiogene Pharm Ltd | Vascular damaging agents |
| CO4960662A1 (es) | 1997-08-28 | 2000-09-25 | Novartis Ag | Ciertos acidos 5-alquil-2-arilaminofenilaceticos y sus derivados |
| US5942532A (en) | 1997-09-05 | 1999-08-24 | Ortho Pharmaceutical Corporation | 2-substituted phenyl-benzimidazole antibacterial agents |
| WO1999014194A1 (en) | 1997-09-12 | 1999-03-25 | Merck Frosst Canada & Co. | 2,3,5-trisubstituted pyridines as inhibitors of cyclooxygenase-2 |
| KR100340273B1 (ko) | 1997-10-14 | 2002-06-14 | 야마모토 카즈모토 | 비페닐-5-알칸산 유도체 및 이의 용도 |
| GB9900334D0 (en) | 1999-01-07 | 1999-02-24 | Angiogene Pharm Ltd | Tricylic vascular damaging agents |
| GB9900752D0 (en) | 1999-01-15 | 1999-03-03 | Angiogene Pharm Ltd | Benzimidazole vascular damaging agents |
| DE60025368T2 (de) | 1999-08-23 | 2006-09-14 | Bml Inc. | Verfahren zum identifizieren von prostaglandin d2 rezeptor modulatoren |
| AU7073400A (en) | 1999-08-27 | 2001-03-26 | Eli Lilly And Company | Biaryl-oxa(thia)zole derivatives and their use as ppars modulators |
| WO2001060807A1 (en) * | 2000-02-18 | 2001-08-23 | Merck & Co. Inc. | Aryloxyacetic acids for diabetes and lipid disorders |
| WO2001081312A2 (en) | 2000-04-24 | 2001-11-01 | Merck Frosst Canada & Co. | Method of treatment using phenyl and biaryl derivatives as prostaglandin e inhibitors and compounds useful therefore |
| NZ522074A (en) | 2000-05-31 | 2004-06-25 | Astrazeneca Ab | Indole derivatives with vascular damaging activity |
| US6699997B2 (en) | 2000-06-28 | 2004-03-02 | Teva Pharmaceutical Industries Ltd. | Carvedilol |
| CA2410562A1 (en) | 2000-07-07 | 2002-01-31 | Angiogene Pharmaceuticals Limited | Colchinol derivatives as angiogenesis inhibitors |
| JP2004502766A (ja) | 2000-07-07 | 2004-01-29 | アンギオジェン・ファーマシューティカルズ・リミテッド | 血管損傷剤としてのコルヒノール誘導体 |
| US6878522B2 (en) * | 2000-07-07 | 2005-04-12 | Baiyong Li | Methods for the identification of compounds useful for the treatment of disease states mediated by prostaglandin D2 |
| US20040097555A1 (en) | 2000-12-26 | 2004-05-20 | Shinegori Ohkawa | Concomitant drugs |
| BR0210391A (pt) | 2001-06-12 | 2004-06-15 | Elan Pharm Inc | Composto, métodos de tratar um paciente que tenha ou de prevenir um paciente de contrair uma doença ou condição e de preparar um composto, e, uso de um composto |
| BR0307406A (pt) | 2002-02-01 | 2004-12-28 | Hoffmann La Roche | Indóis substituìdos como agonistas alfa-1 |
| SE0200411D0 (sv) | 2002-02-05 | 2002-02-05 | Astrazeneca Ab | Novel use |
| WO2003068744A1 (en) | 2002-02-18 | 2003-08-21 | Ishihara Sangyo Kaisha, Ltd. | Pyridine derivatives or salts thereof and cytokine production inhibitors containing the same |
| NZ535603A (en) | 2002-03-20 | 2007-10-26 | Metabolex Inc | Substituted phenylacetic acids |
| JPWO2003097042A1 (ja) * | 2002-05-16 | 2005-09-15 | 塩野義製薬株式会社 | Ｐｇｄ２受容体拮抗剤 |
| JP4484108B2 (ja) | 2002-05-16 | 2010-06-16 | 塩野義製薬株式会社 | Ｐｇｄ２受容体拮抗作用を有する化合物 |
| SE0201635D0 (sv) | 2002-05-30 | 2002-05-30 | Astrazeneca Ab | Novel compounds |
| SE0202241D0 (sv) | 2002-07-17 | 2002-07-17 | Astrazeneca Ab | Novel Compounds |
| AR042206A1 (es) | 2002-11-26 | 2005-06-15 | Novartis Ag | Acidos fenilaceticos y derivados |
| AU2003297398B2 (en) | 2002-12-20 | 2009-09-24 | Amgen Inc. | Asthma and allergic inflammation modulators |
| AU2004232682B2 (en) | 2003-03-28 | 2006-12-07 | Eli Lilly And Company | Isoquinoline-5-sulfonic acid amides as inhibitors of Akt (protein kinase B) |
| SE0301010D0 (sv) | 2003-04-07 | 2003-04-07 | Astrazeneca Ab | Novel compounds |
| SE0301009D0 (sv) * | 2003-04-07 | 2003-04-07 | Astrazeneca Ab | Novel compounds |
| ATE316077T1 (de) | 2003-04-25 | 2006-02-15 | Actimis Pharmaceuticals Inc | Pyrimidin-essigsäure derivate geeignet zur behandlung von crth2-bedingten krankheiten |
| SA04250253B1 (ar) | 2003-08-21 | 2009-11-10 | استرازينيكا ايه بي | احماض فينوكسي اسيتيك مستبدلة باعتبارها مركبات صيدلانية لعلاج الامراض التنفسية مثل الربو ومرض الانسداد الرئوي المزمن |
| GB0324763D0 (en) | 2003-10-23 | 2003-11-26 | Oxagen Ltd | Use of compounds in therapy |
| US7166738B2 (en) | 2004-04-23 | 2007-01-23 | Roche Palo Alto Llc | Non-nucleoside reverse transcriptase inhibitors |
| GB0409921D0 (en) | 2004-05-04 | 2004-06-09 | Novartis Ag | Organic compounds |
| US8022063B2 (en) | 2004-05-29 | 2011-09-20 | 7Tm Pharma A/S | CRTH2 receptor ligands for medicinal uses |
| GB0415320D0 (en) | 2004-07-08 | 2004-08-11 | Astrazeneca Ab | Novel compounds |
| GB0418830D0 (en) | 2004-08-24 | 2004-09-22 | Astrazeneca Ab | Novel compounds |
| GB0422057D0 (en) | 2004-10-05 | 2004-11-03 | Astrazeneca Ab | Novel compounds |
| JP5208510B2 (ja) | 2004-11-23 | 2013-06-12 | アストラゼネカ・アクチエボラーグ | 呼吸器疾患の処置に有用なフェノキシ酢酸誘導体 |
| GB0510584D0 (en) | 2005-05-24 | 2005-06-29 | Novartis Ag | Organic compounds |
| TW200745003A (en) | 2005-10-06 | 2007-12-16 | Astrazeneca Ab | Novel compounds |
| JP5155171B2 (ja) | 2005-10-06 | 2013-02-27 | アストラゼネカ・アクチエボラーグ | 新規化合物 |
| US20080255150A1 (en) | 2005-11-05 | 2008-10-16 | Astrazeneca Ab | Novel Compounds |
| EP1963259B1 (en) | 2005-12-15 | 2012-02-15 | AstraZeneca AB | Substituted diphenylethers, -amines, -sulfides and -methanes for the treatment of respiratory disease |
| UA100983C2 (ru) | 2007-07-05 | 2013-02-25 | Астразенека Аб | Бифенилоксипропановая кислота как модулятор crth2 и интермедиаты |
-
2003
- 2003-04-07 SE SE0301010A patent/SE0301010D0/xx unknown
-
2004
- 2004-03-26 TW TW093108313A patent/TWI336322B/zh not_active IP Right Cessation
- 2004-04-05 MY MYPI20041241A patent/MY149463A/en unknown
- 2004-04-06 NZ NZ542972A patent/NZ542972A/en not_active IP Right Cessation
- 2004-04-06 EP EP04726044.3A patent/EP1611091B1/en not_active Expired - Lifetime
- 2004-04-06 MX MXPA05010682A patent/MXPA05010682A/es active IP Right Grant
- 2004-04-06 JP JP2006508007A patent/JP4898428B2/ja not_active Expired - Fee Related
- 2004-04-06 DK DK04726044.3T patent/DK1611091T3/en active
- 2004-04-06 BR BRPI0409109-4A patent/BRPI0409109A/pt not_active IP Right Cessation
- 2004-04-06 CN CN200480013447A patent/CN100575330C/zh not_active Expired - Fee Related
- 2004-04-06 CA CA2521425A patent/CA2521425C/en not_active Expired - Fee Related
- 2004-04-06 SI SI200432206T patent/SI1611091T1/sl unknown
- 2004-04-06 PL PL04726044T patent/PL1611091T3/pl unknown
- 2004-04-06 US US10/551,783 patent/US8158820B2/en not_active Expired - Fee Related
- 2004-04-06 WO PCT/SE2004/000535 patent/WO2004089885A1/en not_active Ceased
- 2004-04-06 RU RU2005131732/04A patent/RU2372330C2/ru not_active IP Right Cessation
- 2004-04-06 KR KR1020057018996A patent/KR101061339B1/ko not_active Expired - Fee Related
- 2004-04-06 PT PT47260443T patent/PT1611091E/pt unknown
- 2004-04-06 AU AU2004228599A patent/AU2004228599B2/en not_active Ceased
- 2004-04-06 ES ES04726044.3T patent/ES2525763T3/es not_active Expired - Lifetime
- 2004-04-07 AR ARP040101180A patent/AR043998A1/es unknown
-
2005
- 2005-10-04 CO CO05100592A patent/CO5640047A2/es not_active Application Discontinuation
- 2005-10-06 ZA ZA200508088A patent/ZA200508088B/en unknown
- 2005-10-31 IS IS8108A patent/IS8108A/is unknown
- 2005-11-04 NO NO20055219A patent/NO20055219L/no not_active Application Discontinuation
-
2010
- 2010-12-30 US US12/982,435 patent/US20110166117A1/en not_active Abandoned
-
2014
- 2014-12-17 CY CY20141101063T patent/CY1115940T1/el unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2006522118A5 (enExample) | ||
| RU2005131732A (ru) | Новые соединения | |
| RU2309946C2 (ru) | Новые соединения в качестве противовоспалительных, иммуномодулирующих и противопролиферативных агентов | |
| RU2353616C2 (ru) | Производные 2-пиридона в качестве ингибиторов эластазы нейтрофилов и их применение | |
| RU2006107653A (ru) | Связующее вспомогательное вещество и приготовленная на его основе таблетка в форме капли | |
| RU2012131840A (ru) | Новое производное 3-гидрокси-5-арилизотиазола | |
| RU2007132262A (ru) | Соединения и композиции в качестве ингибиторов протеинкиназ | |
| JP6294277B2 (ja) | Ｈｅｃ１活性の調節因子およびそのための方法 | |
| JP2010517946A5 (enExample) | ||
| JP2011502956A5 (enExample) | ||
| RU2001132139A (ru) | Имидазохинолины с сульфонамидными или сульфамидным замещением | |
| JP2006506439A5 (enExample) | ||
| RU2012125372A (ru) | Производные пиразола в качестве ингибиторов 11-бета-hsd1 | |
| JP2019509276A5 (enExample) | ||
| ZA200306991B (en) | Anthranilic acid amides, method for the production thereof, their use as antiarrhythmia agents, and pharmaceutical preparations thereof. | |
| JP2017502940A5 (enExample) | ||
| JP2010524942A5 (enExample) | ||
| RU2007107189A (ru) | Производные арилпиридина | |
| CA2490888A1 (en) | Diaminopyrimidinecarboxamide derivative | |
| JP2008110984A5 (enExample) | ||
| RU2004126936A (ru) | Производные хинолина в качестве антагонистов npv | |
| RU2007121507A (ru) | Соединения аминохиназолинов | |
| RU2007101236A (ru) | Новые гидантоиновые производные для лечения обструктивных заболеваний дыхательных путей | |
| JP2009515949A5 (enExample) | ||
| JP2005526696A5 (enExample) |