JP2006522118A5 - - Google Patents
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- 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
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- 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
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| KR101920090B1 (ko) | 2010-07-05 | 2018-11-19 | 이도르시아 파마슈티컬스 리미티드 | 1-페닐-치환된 헤테로시클릴 유도체 및 프로스타글란딘 ｄ２ 수용체 조절자로서 이의 용도 |
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| 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 |
| EP2790696A1 (en) | 2011-12-16 | 2014-10-22 | Atopix Therapeutics Limited | Combination of crth2 antagonist and a proton pump inhibitor for the treatment of eosinophilic esophagitis |
| ES2624379T3 (es) | 2011-12-21 | 2017-07-14 | Idorsia Pharmaceuticals Ltd | Derivados de heterociclilo y su uso como moduladores del receptor de prostaglandina D2 |
| CN104428305A (zh) * | 2012-07-05 | 2015-03-18 | 埃科特莱茵药品有限公司 | 1-苯基-取代的杂环衍生物及其作为前列腺素d2受体调节剂的用途 |
| DK3013796T3 (da) | 2013-06-27 | 2020-03-16 | Lg Chemical Ltd | Biarylderivater som gpr120-agonister |
| 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 |
| UA117254C2 (uk) * | 2013-09-17 | 2018-07-10 | Вектус Байосистемз Лімітед | Композиція (варіанти) для лікування гіпертензії та/або фіброзу |
| WO2015163435A1 (ja) * | 2014-04-24 | 2015-10-29 | 田辺三菱製薬株式会社 | 新規２－アミノ－ピリジン及び２－アミノ－ピリミジン誘導体及びその医薬用途 |
| 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 |
| CA2986611C (en) | 2015-06-15 | 2023-10-03 | Nmd Pharma Aps | Compounds for use in treating neuromuscular disorders |
| US12440477B2 (en) | 2017-12-14 | 2025-10-14 | 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 |
| US11730714B2 (en) | 2017-12-14 | 2023-08-22 | 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 |
| US10385028B2 (en) | 2017-12-14 | 2019-08-20 | 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 |
| PL3986878T3 (pl) * | 2019-06-19 | 2025-01-20 | Nmd Pharma A/S | Sposób wytwarzania inhibitorów kanału chlorkowego clc-1 |
| CN117142949A (zh) * | 2023-08-31 | 2023-12-01 | 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 | ||
| ES431425A1 (es) | 1973-10-29 | 1977-01-16 | Eisai Co Ltd | Un procedimiento para la preparacion de derivados del acido 2-(m-fenoxifenil)-propionico. |
| 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 |
| WO1996000212A1 (en) * | 1994-06-27 | 1996-01-04 | Cytomed, Inc. | Compounds and methods for the treatment of cardiovascular, inflammatory and immune disorders |
| 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 |
| CN1230884A (zh) | 1996-07-22 | 1999-10-06 | 孟山都公司 | 硫羟砜金属蛋白酶抑制剂 |
| EP0839808A1 (en) * | 1996-10-29 | 1998-05-06 | Novartis AG | Pyrazole derivatives, processes for their preparation, and their use as 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 |
| ATE273279T1 (de) | 1997-09-12 | 2004-08-15 | Merck Frosst Canada Inc | 2,3,5-trisubstituierte pyridine als inhibitoren von cyclooxygenase-2 |
| AU735737B2 (en) | 1997-10-14 | 2001-07-12 | Asahi Kasei Kabushiki Kaisha | Biphenyl-5-alkanoic acid derivatives and use thereof |
| 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 |
| EP1211513B1 (en) | 1999-08-23 | 2006-01-04 | BML, Inc. | Method of identifying modulators of prostaglandin d2 receptors |
| AU7073400A (en) | 1999-08-27 | 2001-03-26 | Eli Lilly And Company | Biaryl-oxa(thia)zole derivatives and their use as ppars modulators |
| CA2400021A1 (en) * | 2000-02-18 | 2001-08-23 | Merck & Co., Inc. | Aryloxyacetic acids for diabetes and lipid disorders |
| EP1278734A2 (en) | 2000-04-24 | 2003-01-29 | Merck Frosst Canada & Co. | Method of treatment using phenyl and biaryl derivatives as prostaglandin e inhibitors and compounds useful therefore |
| IL152682A0 (en) | 2000-05-31 | 2003-06-24 | Astrazeneca Ab | Indole derivatives with vascular damaging activity |
| IL153688A0 (en) | 2000-06-28 | 2003-07-06 | Teva Pharma | Carvedilol |
| 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 |
| CA2410562A1 (en) | 2000-07-07 | 2002-01-31 | Angiogene Pharmaceuticals Limited | Colchinol derivatives as angiogenesis inhibitors |
| US20040097555A1 (en) | 2000-12-26 | 2004-05-20 | Shinegori Ohkawa | Concomitant drugs |
| US7067507B2 (en) | 2001-06-12 | 2006-06-27 | Pharmacia & Upjohn Company | Macrocycles useful in the treatment of Alzheimer's disease |
| MXPA04007414A (es) | 2002-02-01 | 2004-10-11 | Hoffmann La Roche | Indoles sustituidos como agonistas alfa-1. |
| SE0200411D0 (sv) | 2002-02-05 | 2002-02-05 | Astrazeneca Ab | Novel use |
| AU2003211427A1 (en) | 2002-02-18 | 2003-09-04 | Ishihara Sangyo Kaisha, Ltd. | Pyridine derivatives or salts thereof and cytokine production inhibitors containing the same |
| AU2003237787B2 (en) | 2002-03-20 | 2008-12-18 | Metabolex, Inc. | Substituted phenylacetic acids |
| WO2003097042A1 (en) * | 2002-05-16 | 2003-11-27 | Shionogi & Co., Ltd. | Pgd2 receptor antagonist |
| US7534897B2 (en) | 2002-05-16 | 2009-05-19 | Shionogi & Co., Ltd. | Indole arylsulfonaimide compounds exhibiting PGD 2 receptor antagonism |
| SE0201635D0 (sv) | 2002-05-30 | 2002-05-30 | Astrazeneca Ab | Novel compounds |
| SE0202241D0 (sv) | 2002-07-17 | 2002-07-17 | Astrazeneca Ab | Novel Compounds |
| PE20040844A1 (es) | 2002-11-26 | 2004-12-30 | Novartis Ag | Acidos fenilaceticos y derivados como inhibidores de la cox-2 |
| CA2511214C (en) | 2002-12-20 | 2012-12-18 | Tularik, Inc. | Asthma and allergic inflammation modulators |
| CN1768040A (zh) * | 2003-03-28 | 2006-05-03 | 伊莱利利公司 | 作为akt(蛋白激酶b)抑制剂的异喹啉－5－磺酸酰胺 |
| SE0301010D0 (sv) | 2003-04-07 | 2003-04-07 | Astrazeneca Ab | Novel compounds |
| SE0301009D0 (sv) | 2003-04-07 | 2003-04-07 | Astrazeneca Ab | Novel compounds |
| ES2257616T3 (es) | 2003-04-25 | 2006-08-01 | Actimis Pharmaceuticals, Inc. | Derivados del acido pirimidinilacetico utiles para el tratamiento de enfermedades mediadas por crth2. |
| 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 |
| AR051966A1 (es) | 2004-11-23 | 2007-02-21 | Astrazeneca Ab | Derivados de acido fenoxiacetico utiles para el tratamiento de enfermedades respiratorias |
| GB0510584D0 (en) | 2005-05-24 | 2005-06-29 | Novartis Ag | Organic compounds |
| TW200745003A (en) | 2005-10-06 | 2007-12-16 | Astrazeneca Ab | Novel compounds |
| WO2007039736A1 (en) | 2005-10-06 | 2007-04-12 | Astrazeneca Ab | Novel compounds |
| JP2009514935A (ja) | 2005-11-05 | 2009-04-09 | アストラゼネカ・アクチエボラーグ | 新規化合物 |
| EP2305640A3 (en) | 2005-12-15 | 2011-07-20 | AstraZeneca AB | Substituted diphenyl-ethers, -amines, -sulfides and -methanes for the treatment of respiratory diseases |
| 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
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- 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 PL PL04726044T patent/PL1611091T3/pl unknown
- 2004-04-06 MX MXPA05010682A patent/MXPA05010682A/es active IP Right Grant
- 2004-04-06 KR KR1020057018996A patent/KR101061339B1/ko not_active Expired - Fee Related
- 2004-04-06 DK DK04726044.3T patent/DK1611091T3/en active
- 2004-04-06 SI SI200432206T patent/SI1611091T1/sl unknown
- 2004-04-06 PT PT47260443T patent/PT1611091E/pt unknown
- 2004-04-06 US US10/551,783 patent/US8158820B2/en not_active Expired - Fee Related
- 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 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 NZ NZ542972A patent/NZ542972A/en not_active IP Right Cessation
- 2004-04-06 AU AU2004228599A patent/AU2004228599B2/en not_active Ceased
- 2004-04-06 ES ES04726044.3T patent/ES2525763T3/es not_active Expired - Lifetime
- 2004-04-06 BR BRPI0409109-4A patent/BRPI0409109A/pt not_active IP Right Cessation
- 2004-04-06 JP JP2006508007A patent/JP4898428B2/ja not_active Expired - Fee Related
- 2004-04-06 EP EP04726044.3A patent/EP1611091B1/en not_active Expired - Lifetime
- 2004-04-07 AR ARP040101180A patent/AR043998A1/es unknown
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- 2005-10-06 ZA ZA200508088A patent/ZA200508088B/en unknown
- 2005-10-31 IS IS8108A patent/IS8108A/is unknown
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-
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- 2014-12-17 CY CY20141101063T patent/CY1115940T1/el unknown
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