JP2008510778A5 - - Google Patents
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- Publication number
- JP2008510778A5 JP2008510778A5 JP2007528960A JP2007528960A JP2008510778A5 JP 2008510778 A5 JP2008510778 A5 JP 2008510778A5 JP 2007528960 A JP2007528960 A JP 2007528960A JP 2007528960 A JP2007528960 A JP 2007528960A JP 2008510778 A5 JP2008510778 A5 JP 2008510778A5
- Authority
- JP
- Japan
- Prior art keywords
- biphenyl
- oxy
- chloro
- fluoro
- propanoic acid
- 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 18
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 9
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- KOUOVRBERGDLTB-NSHDSACASA-N (2s)-2-[4-chloro-2-(2,5-difluoro-4-morpholin-4-ylsulfonylphenyl)phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1C1=CC(F)=C(S(=O)(=O)N2CCOCC2)C=C1F KOUOVRBERGDLTB-NSHDSACASA-N 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 3
- 235000019260 propionic acid Nutrition 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- QLAVPSXZYRYIPC-JTQLQIEISA-N (2s)-2-[2-[4-ethylsulfonyl-3-(trifluoromethyl)phenyl]-4-(trifluoromethyl)phenoxy]propanoic acid Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)CC)=CC=C1C1=CC(C(F)(F)F)=CC=C1O[C@@H](C)C(O)=O QLAVPSXZYRYIPC-JTQLQIEISA-N 0.000 claims description 2
- WRQIRYJIAFFXPN-VIFPVBQESA-N (2s)-2-[2-[4-methylsulfonyl-3-(trifluoromethyl)phenyl]-4-(trifluoromethyl)phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(C(F)(F)F)C=C1C1=CC=C(S(C)(=O)=O)C(C(F)(F)F)=C1 WRQIRYJIAFFXPN-VIFPVBQESA-N 0.000 claims description 2
- GOZQWZLHIJSPTD-VIFPVBQESA-N (2s)-2-[4-chloro-2-(3-chloro-4-methylsulfonylphenyl)phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1C1=CC=C(S(C)(=O)=O)C(Cl)=C1 GOZQWZLHIJSPTD-VIFPVBQESA-N 0.000 claims description 2
- DEFJYXNDIROMLR-UHFFFAOYSA-N 2-[2-(3-fluoro-4-propan-2-ylsulfonylphenyl)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound C1=C(F)C(S(=O)(=O)C(C)C)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O DEFJYXNDIROMLR-UHFFFAOYSA-N 0.000 claims description 2
- COTOHMPVXMBOHX-UHFFFAOYSA-N 2-[2-[4-ethylsulfonyl-3-(trifluoromethyl)phenyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)CC)=CC=C1C1=CC(C(F)(F)F)=CC=C1OCC(O)=O COTOHMPVXMBOHX-UHFFFAOYSA-N 0.000 claims description 2
- RTPLFCSOWYFWOG-UHFFFAOYSA-N 2-[4-chloro-2-(3-chloro-4-methylsulfinylphenyl)phenoxy]acetic acid Chemical compound C1=C(Cl)C(S(=O)C)=CC=C1C1=CC(Cl)=CC=C1OCC(O)=O RTPLFCSOWYFWOG-UHFFFAOYSA-N 0.000 claims description 2
- PUKFXDCWBBYHTL-UHFFFAOYSA-N 2-[4-chloro-2-(3-chloro-4-methylsulfonylphenyl)phenoxy]acetic acid Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1C1=CC(Cl)=CC=C1OCC(O)=O PUKFXDCWBBYHTL-UHFFFAOYSA-N 0.000 claims description 2
- MSJJLHUUPSIOAU-UHFFFAOYSA-N 2-[4-chloro-2-[4-methylsulfonyl-3-(trifluoromethyl)phenyl]phenoxy]acetic acid Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)C)=CC=C1C1=CC(Cl)=CC=C1OCC(O)=O MSJJLHUUPSIOAU-UHFFFAOYSA-N 0.000 claims description 2
- VZBLMOJEAFVHIR-UHFFFAOYSA-N 2-[4-fluoro-2-[4-methylsulfonyl-3-(trifluoromethyl)phenyl]phenoxy]acetic acid Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)C)=CC=C1C1=CC(F)=CC=C1OCC(O)=O VZBLMOJEAFVHIR-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 230000001404 mediated effect Effects 0.000 claims 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 208000023504 respiratory system disease Diseases 0.000 claims 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 229940094443 oxytocics prostaglandins Drugs 0.000 claims 2
- 239000001294 propane Substances 0.000 claims 2
- 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 2
- 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 2
- 150000003180 prostaglandins Chemical class 0.000 claims 2
- 206010039083 rhinitis Diseases 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- ZWKNQWODTHIBQF-NSHDSACASA-N (2s)-2-[2-[3-fluoro-4-(propan-2-ylcarbamoyl)phenyl]-4-(trifluoromethyl)phenoxy]propanoic acid Chemical compound C1=C(F)C(C(=O)NC(C)C)=CC=C1C1=CC(C(F)(F)F)=CC=C1O[C@@H](C)C(O)=O ZWKNQWODTHIBQF-NSHDSACASA-N 0.000 claims 1
- PTPMTVQCUHVDCM-LBPRGKRZSA-N (2s)-2-[2-[3-fluoro-4-(pyrrolidine-1-carbonyl)phenyl]-4-(trifluoromethyl)phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(C(F)(F)F)C=C1C(C=C1F)=CC=C1C(=O)N1CCCC1 PTPMTVQCUHVDCM-LBPRGKRZSA-N 0.000 claims 1
- CPZCOSTWUZZEBG-AWEZNQCLSA-N (2s)-2-[2-[3-methyl-4-(pyrrolidine-1-carbonyl)phenyl]-4-(trifluoromethyl)phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(C(F)(F)F)C=C1C(C=C1C)=CC=C1C(=O)N1CCCC1 CPZCOSTWUZZEBG-AWEZNQCLSA-N 0.000 claims 1
- PNAULFGEKWYPEQ-LBPRGKRZSA-N (2s)-2-[2-[4-(cyclopentylcarbamoyl)-3-fluorophenyl]-4-(trifluoromethyl)phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(C(F)(F)F)C=C1C(C=C1F)=CC=C1C(=O)NC1CCCC1 PNAULFGEKWYPEQ-LBPRGKRZSA-N 0.000 claims 1
- DUZZYBVTBREVEA-JTQLQIEISA-N (2s)-2-[2-[4-(ethylcarbamoyl)-3-fluorophenyl]-4-(trifluoromethyl)phenoxy]propanoic acid Chemical compound C1=C(F)C(C(=O)NCC)=CC=C1C1=CC(C(F)(F)F)=CC=C1O[C@@H](C)C(O)=O DUZZYBVTBREVEA-JTQLQIEISA-N 0.000 claims 1
- INJYVJAMXPSKEC-NSHDSACASA-N (2s)-2-[2-[4-(tert-butylcarbamoyl)-3-fluorophenyl]-4-(trifluoromethyl)phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(C(F)(F)F)C=C1C1=CC=C(C(=O)NC(C)(C)C)C(F)=C1 INJYVJAMXPSKEC-NSHDSACASA-N 0.000 claims 1
- YYKVKWDQSHNKPS-NSHDSACASA-N (2s)-2-[2-[4-(tert-butylcarbamoyl)-3-fluorophenyl]-4-chlorophenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1C1=CC=C(C(=O)NC(C)(C)C)C(F)=C1 YYKVKWDQSHNKPS-NSHDSACASA-N 0.000 claims 1
- QYLONNMSQMJJNU-ZDUSSCGKSA-N (2s)-2-[2-[4-(tert-butylcarbamoyl)-3-methylphenyl]-4-chlorophenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1C1=CC=C(C(=O)NC(C)(C)C)C(C)=C1 QYLONNMSQMJJNU-ZDUSSCGKSA-N 0.000 claims 1
- VKPNMMZWRIRSPJ-VIFPVBQESA-N (2s)-2-[4-chloro-2-(3-fluoro-4-methylsulfonylphenyl)phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1C1=CC=C(S(C)(=O)=O)C(F)=C1 VKPNMMZWRIRSPJ-VIFPVBQESA-N 0.000 claims 1
- QAZFELYFRXBYRC-LBPRGKRZSA-N (2s)-2-[4-chloro-2-[3-chloro-4-(pyrrolidine-1-carbonyl)phenyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1C(C=C1Cl)=CC=C1C(=O)N1CCCC1 QAZFELYFRXBYRC-LBPRGKRZSA-N 0.000 claims 1
- LYJDDJHDTLWGTQ-LBPRGKRZSA-N (2s)-2-[4-chloro-2-[3-fluoro-4-(2-methylbutan-2-ylcarbamoyl)phenyl]phenoxy]propanoic acid Chemical compound C1=C(F)C(C(=O)NC(C)(C)CC)=CC=C1C1=CC(Cl)=CC=C1O[C@@H](C)C(O)=O LYJDDJHDTLWGTQ-LBPRGKRZSA-N 0.000 claims 1
- QUNTXHCQSHNMJD-LBPRGKRZSA-N (2s)-2-[4-chloro-2-[3-fluoro-4-(2-methylpropylcarbamoyl)phenyl]phenoxy]propanoic acid Chemical compound C1=C(F)C(C(=O)NCC(C)C)=CC=C1C1=CC(Cl)=CC=C1O[C@@H](C)C(O)=O QUNTXHCQSHNMJD-LBPRGKRZSA-N 0.000 claims 1
- UXVQKIOREWHLPH-ABLWVSNPSA-N (2s)-2-[4-chloro-2-[3-fluoro-4-(2-methylpyrrolidine-1-carbonyl)phenyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1C(C=C1F)=CC=C1C(=O)N1C(C)CCC1 UXVQKIOREWHLPH-ABLWVSNPSA-N 0.000 claims 1
- WLSSFRAXKAMBSN-ZDUSSCGKSA-N (2s)-2-[4-chloro-2-[3-fluoro-4-(3-methylbutylcarbamoyl)phenyl]phenoxy]propanoic acid Chemical compound C1=C(F)C(C(=O)NCCC(C)C)=CC=C1C1=CC(Cl)=CC=C1O[C@@H](C)C(O)=O WLSSFRAXKAMBSN-ZDUSSCGKSA-N 0.000 claims 1
- KKGVTNLDRRNPIP-VIFPVBQESA-N (2s)-2-[4-chloro-2-[3-fluoro-4-(methylcarbamoyl)phenyl]phenoxy]propanoic acid Chemical compound C1=C(F)C(C(=O)NC)=CC=C1C1=CC(Cl)=CC=C1O[C@@H](C)C(O)=O KKGVTNLDRRNPIP-VIFPVBQESA-N 0.000 claims 1
- KJBFQNMNZYJLRO-LBPRGKRZSA-N (2s)-2-[4-chloro-2-[3-fluoro-4-(pentan-3-ylcarbamoyl)phenyl]phenoxy]propanoic acid Chemical compound C1=C(F)C(C(=O)NC(CC)CC)=CC=C1C1=CC(Cl)=CC=C1O[C@@H](C)C(O)=O KJBFQNMNZYJLRO-LBPRGKRZSA-N 0.000 claims 1
- ZGDSPOGGCVOJNC-LBPRGKRZSA-N (2s)-2-[4-chloro-2-[3-fluoro-4-(pyrrolidine-1-carbonyl)phenyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1C(C=C1F)=CC=C1C(=O)N1CCCC1 ZGDSPOGGCVOJNC-LBPRGKRZSA-N 0.000 claims 1
- UXVQKIOREWHLPH-OLZOCXBDSA-N (2s)-2-[4-chloro-2-[3-fluoro-4-[(2r)-2-methylpyrrolidine-1-carbonyl]phenyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1C(C=C1F)=CC=C1C(=O)N1[C@H](C)CCC1 UXVQKIOREWHLPH-OLZOCXBDSA-N 0.000 claims 1
- UXVQKIOREWHLPH-STQMWFEESA-N (2s)-2-[4-chloro-2-[3-fluoro-4-[(2s)-2-methylpyrrolidine-1-carbonyl]phenyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1C(C=C1F)=CC=C1C(=O)N1[C@@H](C)CCC1 UXVQKIOREWHLPH-STQMWFEESA-N 0.000 claims 1
- ZEXZISLAHRBLME-AWEZNQCLSA-N (2s)-2-[4-chloro-2-[3-methyl-4-(pyrrolidine-1-carbonyl)phenyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1C(C=C1C)=CC=C1C(=O)N1CCCC1 ZEXZISLAHRBLME-AWEZNQCLSA-N 0.000 claims 1
- ZTQBSOLTFQJYAS-NSHDSACASA-N (2s)-2-[4-chloro-2-[4-(3,3-difluoropyrrolidine-1-carbonyl)-3-fluorophenyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1C(C=C1F)=CC=C1C(=O)N1CC(F)(F)CC1 ZTQBSOLTFQJYAS-NSHDSACASA-N 0.000 claims 1
- VXFPYMJHUQOVKG-NSHDSACASA-N (2s)-2-[4-chloro-2-[4-(cyclobutylcarbamoyl)-3-fluorophenyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1C(C=C1F)=CC=C1C(=O)NC1CCC1 VXFPYMJHUQOVKG-NSHDSACASA-N 0.000 claims 1
- SEMABQFCWXUGNS-LBPRGKRZSA-N (2s)-2-[4-chloro-2-[4-(cyclopentylcarbamoyl)-3-fluorophenyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1C(C=C1F)=CC=C1C(=O)NC1CCCC1 SEMABQFCWXUGNS-LBPRGKRZSA-N 0.000 claims 1
- USAKTMHUVBGRCR-JTQLQIEISA-N (2s)-2-[4-chloro-2-[4-(cyclopropylcarbamoyl)-3-fluorophenyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1C(C=C1F)=CC=C1C(=O)NC1CC1 USAKTMHUVBGRCR-JTQLQIEISA-N 0.000 claims 1
- AZIWOMBYWFIQFP-LBPRGKRZSA-N (2s)-2-[4-chloro-2-[4-(diethylcarbamoyl)-3-fluorophenyl]phenoxy]propanoic acid Chemical compound C1=C(F)C(C(=O)N(CC)CC)=CC=C1C1=CC(Cl)=CC=C1O[C@@H](C)C(O)=O AZIWOMBYWFIQFP-LBPRGKRZSA-N 0.000 claims 1
- URAUYNDQINQGIP-JTQLQIEISA-N (2s)-2-[4-chloro-2-[4-(ethylcarbamoyl)-3-fluorophenyl]phenoxy]propanoic acid Chemical compound C1=C(F)C(C(=O)NCC)=CC=C1C1=CC(Cl)=CC=C1O[C@@H](C)C(O)=O URAUYNDQINQGIP-JTQLQIEISA-N 0.000 claims 1
- QFZICZKRDNEFOM-LBPRGKRZSA-N (2s)-2-[4-chloro-2-[4-(pyrrolidine-1-carbonyl)-3-(trifluoromethyl)phenyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1C(C=C1C(F)(F)F)=CC=C1C(=O)N1CCCC1 QFZICZKRDNEFOM-LBPRGKRZSA-N 0.000 claims 1
- PRQRONVGMWVYFW-NSHDSACASA-N (2s)-2-[4-chloro-2-[4-[ethyl(methyl)carbamoyl]-3-fluorophenyl]phenoxy]propanoic acid Chemical compound C1=C(F)C(C(=O)N(C)CC)=CC=C1C1=CC(Cl)=CC=C1O[C@@H](C)C(O)=O PRQRONVGMWVYFW-NSHDSACASA-N 0.000 claims 1
- PKRAODYTJMIMTC-LBPRGKRZSA-N (2s)-2-[4-chloro-2-[4-morpholin-4-ylsulfonyl-3-(trifluoromethyl)phenyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1C1=CC=C(S(=O)(=O)N2CCOCC2)C(C(F)(F)F)=C1 PKRAODYTJMIMTC-LBPRGKRZSA-N 0.000 claims 1
- UEQAUTJJFKOVRO-LBPRGKRZSA-N (2s)-2-[4-fluoro-2-[3-fluoro-4-(pyrrolidine-1-carbonyl)phenyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(F)C=C1C(C=C1F)=CC=C1C(=O)N1CCCC1 UEQAUTJJFKOVRO-LBPRGKRZSA-N 0.000 claims 1
- QGHTWZBBNYERQW-UHFFFAOYSA-N 2-[2-[3-fluoro-4-(pyrrolidine-1-carbonyl)phenyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1C(C=C1F)=CC=C1C(=O)N1CCCC1 QGHTWZBBNYERQW-UHFFFAOYSA-N 0.000 claims 1
- IYXPIDVTZHPTIN-UHFFFAOYSA-N 2-[2-[3-methyl-4-(piperidine-1-carbonyl)phenyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=CC(C=2C(=CC=C(C=2)C(F)(F)F)OCC(O)=O)=CC=C1C(=O)N1CCCCC1 IYXPIDVTZHPTIN-UHFFFAOYSA-N 0.000 claims 1
- ZMAIHUBEOTZHBC-UHFFFAOYSA-N 2-[2-[3-methyl-4-(pyrrolidine-1-carbonyl)phenyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=CC(C=2C(=CC=C(C=2)C(F)(F)F)OCC(O)=O)=CC=C1C(=O)N1CCCC1 ZMAIHUBEOTZHBC-UHFFFAOYSA-N 0.000 claims 1
- UKUAESGBUKHDFJ-UHFFFAOYSA-N 2-[4-chloro-2-[3-chloro-4-(1,2-oxazolidine-2-carbonyl)phenyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1C(C=C1Cl)=CC=C1C(=O)N1OCCC1 UKUAESGBUKHDFJ-UHFFFAOYSA-N 0.000 claims 1
- NPWJPUJPPKVZSJ-UHFFFAOYSA-N 2-[4-chloro-2-[3-chloro-4-(2-methylpyrrolidine-1-carbonyl)phenyl]phenoxy]acetic acid Chemical compound CC1CCCN1C(=O)C1=CC=C(C=2C(=CC=C(Cl)C=2)OCC(O)=O)C=C1Cl NPWJPUJPPKVZSJ-UHFFFAOYSA-N 0.000 claims 1
- FNJRYAYRFWBZRU-UHFFFAOYSA-N 2-[4-chloro-2-[3-chloro-4-(morpholine-4-carbonyl)phenyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1C(C=C1Cl)=CC=C1C(=O)N1CCOCC1 FNJRYAYRFWBZRU-UHFFFAOYSA-N 0.000 claims 1
- IUQBGJLTSZXBBC-UHFFFAOYSA-N 2-[4-chloro-2-[3-chloro-4-(pyrrolidine-1-carbonyl)phenyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1C(C=C1Cl)=CC=C1C(=O)N1CCCC1 IUQBGJLTSZXBBC-UHFFFAOYSA-N 0.000 claims 1
- FBTAKDCLJGEXIA-OKILXGFUSA-N 2-[4-chloro-2-[3-chloro-4-[(2r,6s)-2,6-dimethylpiperidine-1-carbonyl]phenyl]phenoxy]acetic acid Chemical compound C[C@H]1CCC[C@@H](C)N1C(=O)C1=CC=C(C=2C(=CC=C(Cl)C=2)OCC(O)=O)C=C1Cl FBTAKDCLJGEXIA-OKILXGFUSA-N 0.000 claims 1
- UINIKFHCWUZECM-UHFFFAOYSA-N 2-[4-chloro-2-[3-fluoro-4-(methylcarbamoyl)phenyl]phenoxy]acetic acid Chemical compound C1=C(F)C(C(=O)NC)=CC=C1C1=CC(Cl)=CC=C1OCC(O)=O UINIKFHCWUZECM-UHFFFAOYSA-N 0.000 claims 1
- YVTWRMXSPMKKFQ-UHFFFAOYSA-N 2-[4-chloro-2-[3-fluoro-4-(pentan-3-ylcarbamoyl)phenyl]phenoxy]acetic acid Chemical compound C1=C(F)C(C(=O)NC(CC)CC)=CC=C1C1=CC(Cl)=CC=C1OCC(O)=O YVTWRMXSPMKKFQ-UHFFFAOYSA-N 0.000 claims 1
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| JP6097765B2 (ja) | 2011-12-21 | 2017-03-15 | 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 | 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 |
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| WO2007052023A2 (en) | 2005-11-05 | 2007-05-10 | Astrazeneca Ab | Novel compounds |
| ATE545637T1 (de) | 2005-12-15 | 2012-03-15 | Astrazeneca Ab | Substituierte diphenylether, -amine, -sulfide und methane zur behandlung von atemwegserkrankungen |
| UA100983C2 (ru) | 2007-07-05 | 2013-02-25 | Астразенека Аб | Бифенилоксипропановая кислота как модулятор crth2 и интермедиаты |
-
2004
- 2004-08-24 GB GBGB0418830.6A patent/GB0418830D0/en not_active Ceased
-
2005
- 2005-08-19 AR ARP050103487A patent/AR053092A1/es unknown
- 2005-08-22 CA CA002575200A patent/CA2575200A1/en not_active Abandoned
- 2005-08-22 MX MX2007002095A patent/MX2007002095A/es not_active Application Discontinuation
- 2005-08-22 EP EP05773308A patent/EP1784388B3/en not_active Expired - Lifetime
- 2005-08-22 CN CN2005800364721A patent/CN101048369B/zh not_active Expired - Fee Related
- 2005-08-22 BR BRPI0514448-5A patent/BRPI0514448A/pt not_active Application Discontinuation
- 2005-08-22 RU RU2007106039/04A patent/RU2007106039A/ru unknown
- 2005-08-22 AT AT05773308T patent/ATE447551T1/de not_active IP Right Cessation
- 2005-08-22 DE DE602005017503T patent/DE602005017503D1/de not_active Expired - Lifetime
- 2005-08-22 US US11/574,076 patent/US7737135B2/en not_active Expired - Fee Related
- 2005-08-22 WO PCT/GB2005/003255 patent/WO2006021759A1/en not_active Ceased
- 2005-08-22 KR KR1020077004365A patent/KR20070047319A/ko not_active Withdrawn
- 2005-08-22 AU AU2005276281A patent/AU2005276281A1/en not_active Abandoned
- 2005-08-22 JP JP2007528960A patent/JP4990773B2/ja not_active Expired - Fee Related
- 2005-08-22 ES ES05773308T patent/ES2335425T7/es active Active
- 2005-08-23 UY UY29079A patent/UY29079A1/es not_active Application Discontinuation
- 2005-08-23 TW TW094128765A patent/TW200621690A/zh unknown
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2007
- 2007-01-29 IL IL181049A patent/IL181049A0/en unknown
- 2007-02-22 ZA ZA200701584A patent/ZA200701584B/xx unknown
- 2007-03-26 NO NO20071577A patent/NO20071577L/no not_active Application Discontinuation
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2009
- 2009-12-18 US US12/642,244 patent/US8163727B2/en not_active Expired - Fee Related
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2011
- 2011-12-06 US US13/311,647 patent/US8722741B2/en not_active Expired - Fee Related
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