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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| MX2010003621A (es) * | 2007-10-01 | 2010-04-14 | Hoffmann La Roche | N-heterociclil biaril carboxamidas como antagonistas del receptor ccr. |
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| CN104114169A (zh) | 2011-12-16 | 2014-10-22 | 阿托佩斯治疗有限公司 | 用于治疗嗜酸细胞性食管炎的crth2拮抗剂和质子泵抑制剂的组合物 |
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| EP2885307A1 (en) | 2012-07-05 | 2015-06-24 | Actelion Pharmaceuticals Ltd. | 1-phenyl-substituted heterocyclyl derivatives and their use as prostaglandin d2 receptor modulators |
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| US10513504B2 (en) | 2018-03-08 | 2019-12-24 | Apotex Inc. | Processes for the preparation of apalutamide and intermediates thereof |
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Family Cites Families (73)
| 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 |
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| SE419538B (sv) * | 1973-10-29 | 1981-08-10 | Eisai Co Ltd | Analogiforfaranden for framstellning av 2-(n-fenoxfenyl)-propionsyraderivat |
| 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 |
| 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 |
| CN1200106A (zh) | 1995-08-28 | 1998-11-25 | 美国家用产品公司 | 苯氧基乙酸类化合物用作醛糖还原酶抑制剂和抗高血糖药 |
| DE19544828A1 (de) * | 1995-12-01 | 1997-06-05 | Hoechst Ag | Hochmolekulare Copolymere |
| ATE233552T1 (de) | 1996-07-22 | 2003-03-15 | Monsanto Co | Thiol-sulfonen als metalloproteinaseinhibitoren |
| 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 |
| 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 |
| ES2226167T3 (es) | 1997-09-12 | 2005-03-16 | MERCK FROSST CANADA & CO. | Piridinas 2,3,5-sustituidas como inhibidores de ciclooxigenasa 2. |
| CA2304713C (en) * | 1997-10-14 | 2003-06-10 | Asahi Kasei Kogyo Kabushiki Kaisha | Biphenyl-5-alkanoic acid derivatives and use thereof |
| ATE315230T1 (de) | 1999-08-23 | 2006-02-15 | Bml Inc | Verfahren zum identifizieren von prostaglandin d2 rezeptor modulatoren |
| WO2001016120A1 (en) | 1999-08-27 | 2001-03-08 | Eli Lilly And Company | Biaryl-oxa(thia)zole derivatives and their use as ppars modulators |
| JP2003523336A (ja) | 2000-02-18 | 2003-08-05 | メルク エンド カムパニー インコーポレーテッド | 糖尿病及び脂質障害のためのアリールオキシ酢酸 |
| AU2001254555A1 (en) | 2000-04-24 | 2001-11-07 | Merck Frosst Canada & Co | Method of treatment using phenyl and biaryl derivatives as prostaglandin E inhibitors and compounds useful therefore |
| BR0111230A (pt) | 2000-05-31 | 2003-06-10 | Astrazeneca Ab | Composto, e, uso e processo para a preparação do mesmo |
| CA2413702A1 (en) * | 2000-06-28 | 2002-01-03 | Teva Pharmaceuticals Industries Ltd. | Carvedilol |
| 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 |
| EP1395257A1 (en) * | 2001-06-12 | 2004-03-10 | Elan Pharmaceuticals, Inc. | Macrocycles useful in the treatment of alzheimer's disease |
| EP1424335A4 (en) | 2001-09-07 | 2005-11-16 | Ono Pharmaceutical Co | INDOLE DERIVATIVES |
| PL373410A1 (en) | 2002-02-01 | 2005-08-22 | F.Hoffman-La Roche Ag | Substituted indoles as alpha-1 agonists |
| 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 |
| MXPA04009040A (es) | 2002-03-20 | 2005-01-25 | Metabolex Inc | Acidos fenilaceticos sustituidos. |
| EP2423190A1 (en) | 2002-05-16 | 2012-02-29 | Shionogi&Co., Ltd. | Compounds Exhibiting PGD 2 Receptor Antagonism |
| WO2003097042A1 (en) | 2002-05-16 | 2003-11-27 | Shionogi & Co., Ltd. | Pgd2 receptor antagonist |
| 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 |
| ES2401079T3 (es) | 2002-12-20 | 2013-04-16 | Amgen Inc. | Moduladores del asma y de la inflamación alérgica |
| BRPI0408353A (pt) | 2003-03-28 | 2006-03-21 | Lilly Co Eli | composto, composição farmacêutica, métodos para o tratamento de neoplasias suscetìveis e para o tratamento de infecções virais, e, uso de um composto |
| SE0301009D0 (sv) | 2003-04-07 | 2003-04-07 | Astrazeneca Ab | Novel compounds |
| SE0301010D0 (sv) * | 2003-04-07 | 2003-04-07 | Astrazeneca Ab | Novel compounds |
| DE60303238T2 (de) | 2003-04-25 | 2006-09-14 | Actimis Pharmaceuticals, Inc., La Jolla | 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 |
| EP1758579A1 (en) | 2004-05-29 | 2007-03-07 | 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 |
| EP1817282B1 (en) | 2004-11-23 | 2011-07-20 | AstraZeneca AB | Phenoxyacetic acid derivatives useful for treating respiratory diseases |
| GB0510584D0 (en) | 2005-05-24 | 2005-06-29 | Novartis Ag | Organic compounds |
| TW200745003A (en) * | 2005-10-06 | 2007-12-16 | Astrazeneca Ab | Novel compounds |
| EP1937632A1 (en) | 2005-10-06 | 2008-07-02 | Astra Zeneca AB | Novel compounds |
| US20080255150A1 (en) * | 2005-11-05 | 2008-10-16 | Astrazeneca Ab | Novel Compounds |
| ES2380683T3 (es) | 2005-12-15 | 2012-05-17 | Astrazeneca Ab | Difenil-éteres, -amidas, -sulfuros y - metanos sustituidos para el tratamiento de la enfermedad respiratoria |
| 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 AT AT05773308T patent/ATE447551T1/de not_active IP Right Cessation
- 2005-08-22 EP EP05773308A patent/EP1784388B3/en not_active Expired - Lifetime
- 2005-08-22 RU RU2007106039/04A patent/RU2007106039A/ru unknown
- 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 KR KR1020077004365A patent/KR20070047319A/ko not_active Withdrawn
- 2005-08-22 US US11/574,076 patent/US7737135B2/en not_active Expired - Fee Related
- 2005-08-22 CN CN2005800364721A patent/CN101048369B/zh not_active Expired - Fee Related
- 2005-08-22 DE DE602005017503T patent/DE602005017503D1/de not_active Expired - Lifetime
- 2005-08-22 BR BRPI0514448-5A patent/BRPI0514448A/pt not_active Application Discontinuation
- 2005-08-22 MX MX2007002095A patent/MX2007002095A/es not_active Application Discontinuation
- 2005-08-22 CA CA002575200A patent/CA2575200A1/en not_active Abandoned
- 2005-08-22 ES ES05773308T patent/ES2335425T7/es active Active
- 2005-08-22 WO PCT/GB2005/003255 patent/WO2006021759A1/en not_active Ceased
- 2005-08-23 UY UY29079A patent/UY29079A1/es not_active Application Discontinuation
- 2005-08-23 TW TW094128765A patent/TW200621690A/zh unknown
-
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
-
2009
- 2009-12-18 US US12/642,244 patent/US8163727B2/en not_active Expired - Fee Related
-
2011
- 2011-12-06 US US13/311,647 patent/US8722741B2/en not_active Expired - Fee Related
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