JP2008520637A5 - - Google Patents
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- Publication number
- JP2008520637A5 JP2008520637A5 JP2007542103A JP2007542103A JP2008520637A5 JP 2008520637 A5 JP2008520637 A5 JP 2008520637A5 JP 2007542103 A JP2007542103 A JP 2007542103A JP 2007542103 A JP2007542103 A JP 2007542103A JP 2008520637 A5 JP2008520637 A5 JP 2008520637A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- phenoxy
- piperazinyl
- acetic acid
- chloro
- 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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- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 150000002367 halogens Chemical class 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000005418 aryl aryl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- -1 C (O) R 9 Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004429 atoms Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000011780 sodium chloride Substances 0.000 claims description 5
- IXGJAVNJRRZJCZ-UHFFFAOYSA-N 2-[2-[4-(benzenesulfonyl)piperazin-1-yl]-4-chlorophenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1N1CCN(S(=O)(=O)C=2C=CC=CC=2)CC1 IXGJAVNJRRZJCZ-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- FYBIPFSMDCQHGL-INIZCTEOSA-N 2-[2-[[(3S)-4-benzylsulfonyl-3-methylpiperazin-1-yl]methyl]-4-chlorophenoxy]acetic acid Chemical compound C([C@@H](N(CC1)S(=O)(=O)CC=2C=CC=CC=2)C)N1CC1=CC(Cl)=CC=C1OCC(O)=O FYBIPFSMDCQHGL-INIZCTEOSA-N 0.000 claims description 2
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- GMFBGMFMMAVODH-INIZCTEOSA-N 2-[4-chloro-2-[[(3S)-3-methyl-4-(2-phenylacetyl)piperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C=CC=CC=2)C)N1CC1=CC(Cl)=CC=C1OCC(O)=O GMFBGMFMMAVODH-INIZCTEOSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- RRWLYFAHCPGELC-HNNXBMFYSA-N (2S)-2-[2-[(4-benzyl-3-oxopiperazin-1-yl)methyl]-4-chlorophenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1CN1CC(=O)N(CC=2C=CC=CC=2)CC1 RRWLYFAHCPGELC-HNNXBMFYSA-N 0.000 claims 1
- YMRIXJPQOSNAOM-INIZCTEOSA-N (2S)-2-[2-[(4-benzylsulfonylpiperazin-1-yl)methyl]-4-fluorophenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(F)C=C1CN1CCN(S(=O)(=O)CC=2C=CC=CC=2)CC1 YMRIXJPQOSNAOM-INIZCTEOSA-N 0.000 claims 1
- HCLYNTYHESHSGT-HNNXBMFYSA-N (2S)-2-[2-[[4-(benzenesulfonyl)piperazin-1-yl]methyl]-4-fluorophenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(F)C=C1CN1CCN(S(=O)(=O)C=2C=CC=CC=2)CC1 HCLYNTYHESHSGT-HNNXBMFYSA-N 0.000 claims 1
- FWYQUEFNBWXQDJ-GJZGRUSLSA-N (2S)-2-[4-chloro-2-[(3S)-4-[2-(4-chlorophenyl)acetyl]-3-methylpiperazin-1-yl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1N1C[C@H](C)N(C(=O)CC=2C=CC(Cl)=CC=2)CC1 FWYQUEFNBWXQDJ-GJZGRUSLSA-N 0.000 claims 1
- SAJAASZXTYEPFC-GJZGRUSLSA-N (2S)-2-[4-chloro-2-[(3S)-4-[2-(4-fluorophenyl)acetyl]-3-methylpiperazin-1-yl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1N1C[C@H](C)N(C(=O)CC=2C=CC(F)=CC=2)CC1 SAJAASZXTYEPFC-GJZGRUSLSA-N 0.000 claims 1
- XPLZJCKZIQZDEA-IRXDYDNUSA-N (2S)-2-[4-chloro-2-[[(3S)-3-methyl-4-(2-phenylacetyl)piperazin-1-yl]methyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1CN1C[C@H](C)N(C(=O)CC=2C=CC=CC=2)CC1 XPLZJCKZIQZDEA-IRXDYDNUSA-N 0.000 claims 1
- HAKFTQCBZVTOQD-ROUUACIJSA-N (2S)-2-[4-chloro-2-[[(3S)-3-methyl-4-[2-(4-methylphenyl)acetyl]piperazin-1-yl]methyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1CN1C[C@H](C)N(C(=O)CC=2C=CC(C)=CC=2)CC1 HAKFTQCBZVTOQD-ROUUACIJSA-N 0.000 claims 1
- BVOOUBNJHVCDSK-OALUTQOASA-N (2S)-2-[4-chloro-2-[[(3S)-3-methyl-4-[2-(4-propan-2-ylphenyl)acetyl]piperazin-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1CC(=O)N1[C@@H](C)CN(CC=2C(=CC=C(Cl)C=2)O[C@@H](C)C(O)=O)CC1 BVOOUBNJHVCDSK-OALUTQOASA-N 0.000 claims 1
- BSPBODBNPCPHLA-HOTGVXAUSA-N (2S)-2-[4-chloro-2-[[(3S)-3-methyl-4-[2-[4-(trifluoromethyl)phenyl]acetyl]piperazin-1-yl]methyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1CN1C[C@H](C)N(C(=O)CC=2C=CC(=CC=2)C(F)(F)F)CC1 BSPBODBNPCPHLA-HOTGVXAUSA-N 0.000 claims 1
- GMXLSOTXSJJEGA-GJZGRUSLSA-N (2S)-2-[4-chloro-2-[[(3S)-4-[2-(2,4-dichlorophenyl)acetyl]-3-methylpiperazin-1-yl]methyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1CN1C[C@H](C)N(C(=O)CC=2C(=CC(Cl)=CC=2)Cl)CC1 GMXLSOTXSJJEGA-GJZGRUSLSA-N 0.000 claims 1
- NFWJBPHMYAFTNG-GJZGRUSLSA-N (2S)-2-[4-chloro-2-[[(3S)-4-[2-(3,4-dichlorophenyl)acetyl]-3-methylpiperazin-1-yl]methyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1CN1C[C@H](C)N(C(=O)CC=2C=C(Cl)C(Cl)=CC=2)CC1 NFWJBPHMYAFTNG-GJZGRUSLSA-N 0.000 claims 1
- CKABBNCZGDZGAN-GJZGRUSLSA-N (2S)-2-[4-chloro-2-[[(3S)-4-[2-(4-chloro-2-fluorophenyl)acetyl]-3-methylpiperazin-1-yl]methyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1CN1C[C@H](C)N(C(=O)CC=2C(=CC(Cl)=CC=2)F)CC1 CKABBNCZGDZGAN-GJZGRUSLSA-N 0.000 claims 1
- NOEKELZJHSRSCX-IRXDYDNUSA-N (2S)-2-[4-chloro-2-[[(3S)-4-[2-(4-methoxyphenyl)acetyl]-3-methylpiperazin-1-yl]methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC)=CC=C1CC(=O)N1[C@@H](C)CN(CC=2C(=CC=C(Cl)C=2)O[C@@H](C)C(O)=O)CC1 NOEKELZJHSRSCX-IRXDYDNUSA-N 0.000 claims 1
- DKGIDOYCDBRQFD-GJZGRUSLSA-N (2S)-2-[4-chloro-2-[[(3S)-4-[2-[2-fluoro-4-(trifluoromethyl)phenyl]acetyl]-3-methylpiperazin-1-yl]methyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1CN1C[C@H](C)N(C(=O)CC=2C(=CC(=CC=2)C(F)(F)F)F)CC1 DKGIDOYCDBRQFD-GJZGRUSLSA-N 0.000 claims 1
- ZFHRZQDJPFXIRE-INIZCTEOSA-N (2S)-2-[4-fluoro-2-[[4-(2-phenylacetyl)piperazin-1-yl]methyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(F)C=C1CN1CCN(C(=O)CC=2C=CC=CC=2)CC1 ZFHRZQDJPFXIRE-INIZCTEOSA-N 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical group CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims 1
- VTDIWMPYBAVEDY-UHFFFAOYSA-N 1-propylpiperidine Chemical compound CCCN1CCCCC1 VTDIWMPYBAVEDY-UHFFFAOYSA-N 0.000 claims 1
- SXJOQQNGWCJIHX-UHFFFAOYSA-N 2-[2-(4-benzylsulfonylpiperazin-1-yl)-4-chlorophenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1N1CCN(S(=O)(=O)CC=2C=CC=CC=2)CC1 SXJOQQNGWCJIHX-UHFFFAOYSA-N 0.000 claims 1
- ORSWDXYDKIPVGD-UHFFFAOYSA-N 2-[2-[(4-benzoyl-3-methylpiperazin-1-yl)methyl]-4-chlorophenoxy]acetic acid Chemical compound C1CN(C(=O)C=2C=CC=CC=2)C(C)CN1CC1=CC(Cl)=CC=C1OCC(O)=O ORSWDXYDKIPVGD-UHFFFAOYSA-N 0.000 claims 1
- OBMZISABHBNQKD-UHFFFAOYSA-N 2-[2-[(4-benzoylpiperazin-1-yl)methyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1CN1CCN(C(=O)C=2C=CC=CC=2)CC1 OBMZISABHBNQKD-UHFFFAOYSA-N 0.000 claims 1
- FSYMRBYJPOBPII-UHFFFAOYSA-N 2-[2-[(4-benzylsulfonyl-1,4-diazepan-1-yl)methyl]-4-chlorophenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1CN1CCN(S(=O)(=O)CC=2C=CC=CC=2)CCC1 FSYMRBYJPOBPII-UHFFFAOYSA-N 0.000 claims 1
- SRIBGUFBFRUANK-UHFFFAOYSA-N 2-[2-[(4-benzylsulfonyl-2-methylpiperazin-1-yl)methyl]-4-chlorophenoxy]acetic acid Chemical compound CC1CN(S(=O)(=O)CC=2C=CC=CC=2)CCN1CC1=CC(Cl)=CC=C1OCC(O)=O SRIBGUFBFRUANK-UHFFFAOYSA-N 0.000 claims 1
- FYBIPFSMDCQHGL-UHFFFAOYSA-N 2-[2-[(4-benzylsulfonyl-3-methylpiperazin-1-yl)methyl]-4-chlorophenoxy]acetic acid Chemical compound C1CN(S(=O)(=O)CC=2C=CC=CC=2)C(C)CN1CC1=CC(Cl)=CC=C1OCC(O)=O FYBIPFSMDCQHGL-UHFFFAOYSA-N 0.000 claims 1
- JBBOMVFXXYZQQP-UHFFFAOYSA-N 2-[2-[(4-benzylsulfonylpiperazin-1-yl)methyl]-4-chlorophenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1CN1CCN(S(=O)(=O)CC=2C=CC=CC=2)CC1 JBBOMVFXXYZQQP-UHFFFAOYSA-N 0.000 claims 1
- WLFOCYYTIVOUSE-UHFFFAOYSA-N 2-[2-[(4-benzylsulfonylpiperazin-1-yl)methyl]-4-fluorophenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(F)C=C1CN1CCN(S(=O)(=O)CC=2C=CC=CC=2)CC1 WLFOCYYTIVOUSE-UHFFFAOYSA-N 0.000 claims 1
- HMIPQKCYIJRCFK-UHFFFAOYSA-N 2-[2-[1-(4-benzoylpiperazin-1-yl)ethyl]-4-chlorophenoxy]acetic acid Chemical compound C=1C(Cl)=CC=C(OCC(O)=O)C=1C(C)N(CC1)CCN1C(=O)C1=CC=CC=C1 HMIPQKCYIJRCFK-UHFFFAOYSA-N 0.000 claims 1
- YFYBEPKDKMHPHF-UHFFFAOYSA-N 2-[2-[1-[4-(benzenesulfonyl)piperazin-1-yl]ethyl]-4-chlorophenoxy]acetic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C(Cl)=CC=C(OCC(O)=O)C=1C(C)N(CC1)CCN1S(=O)(=O)C1=CC=CC=C1 YFYBEPKDKMHPHF-UHFFFAOYSA-N 0.000 claims 1
- WENXBDQAWPNUHF-UHFFFAOYSA-N 2-[2-[4-(4-fluorophenyl)sulfonylpiperazin-1-yl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1N1CCN(S(=O)(=O)C=2C=CC(F)=CC=2)CC1 WENXBDQAWPNUHF-UHFFFAOYSA-N 0.000 claims 1
- YLPKAFLLNDMZDA-UHFFFAOYSA-N 2-[2-[[(1-benzylsulfonylpyrrolidin-3-yl)amino]methyl]-4-chlorophenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1CNC1CN(S(=O)(=O)CC=2C=CC=CC=2)CC1 YLPKAFLLNDMZDA-UHFFFAOYSA-N 0.000 claims 1
- KQVTZYFUHDWJOQ-OAHLLOKOSA-N 2-[2-[[(2R)-4-(benzenesulfonyl)-2-methylpiperazin-1-yl]methyl]-4-chlorophenoxy]acetic acid Chemical compound C([C@H]1C)N(S(=O)(=O)C=2C=CC=CC=2)CCN1CC1=CC(Cl)=CC=C1OCC(O)=O KQVTZYFUHDWJOQ-OAHLLOKOSA-N 0.000 claims 1
- OVNWHOGUZJEKAS-OAHLLOKOSA-N 2-[2-[[(3R)-4-(benzenesulfonyl)-3-methylpiperazin-1-yl]methyl]-4-chlorophenoxy]acetic acid Chemical compound C([C@H](N(CC1)S(=O)(=O)C=2C=CC=CC=2)C)N1CC1=CC(Cl)=CC=C1OCC(O)=O OVNWHOGUZJEKAS-OAHLLOKOSA-N 0.000 claims 1
- FYBIPFSMDCQHGL-MRXNPFEDSA-N 2-[2-[[(3R)-4-benzylsulfonyl-3-methylpiperazin-1-yl]methyl]-4-chlorophenoxy]acetic acid Chemical compound C([C@H](N(CC1)S(=O)(=O)CC=2C=CC=CC=2)C)N1CC1=CC(Cl)=CC=C1OCC(O)=O FYBIPFSMDCQHGL-MRXNPFEDSA-N 0.000 claims 1
- ZIZVDEBHXJKPLF-INIZCTEOSA-N 2-[2-[[(3S)-3-methyl-4-(2-phenylacetyl)piperazin-1-yl]methyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C=CC=CC=2)C)N1CC1=CC(C(F)(F)F)=CC=C1OCC(O)=O ZIZVDEBHXJKPLF-INIZCTEOSA-N 0.000 claims 1
- RYDKHFBYSXPMIC-SFHVURJKSA-N 2-[2-[[(3S)-4-(benzenesulfonyl)-3-ethylpiperazin-1-yl]methyl]-4-chlorophenoxy]acetic acid Chemical compound C([C@@H](N(CC1)S(=O)(=O)C=2C=CC=CC=2)CC)N1CC1=CC(Cl)=CC=C1OCC(O)=O RYDKHFBYSXPMIC-SFHVURJKSA-N 0.000 claims 1
- SNMDUARWLPWWOD-INIZCTEOSA-N 2-[2-[[(3S)-4-(benzenesulfonyl)-3-methylpiperazin-1-yl]methyl]-4-chlorophenoxy]-2-methylpropanoic acid Chemical compound C([C@@H](N(CC1)S(=O)(=O)C=2C=CC=CC=2)C)N1CC1=CC(Cl)=CC=C1OC(C)(C)C(O)=O SNMDUARWLPWWOD-INIZCTEOSA-N 0.000 claims 1
- OVNWHOGUZJEKAS-HNNXBMFYSA-N 2-[2-[[(3S)-4-(benzenesulfonyl)-3-methylpiperazin-1-yl]methyl]-4-chlorophenoxy]acetic acid Chemical compound C([C@@H](N(CC1)S(=O)(=O)C=2C=CC=CC=2)C)N1CC1=CC(Cl)=CC=C1OCC(O)=O OVNWHOGUZJEKAS-HNNXBMFYSA-N 0.000 claims 1
- SZXBYKZAJAJDDC-IBGZPJMESA-N 2-[2-[[(3S)-4-(benzenesulfonyl)-3-propylpiperazin-1-yl]methyl]-4-chlorophenoxy]acetic acid Chemical compound C([C@@H](N(CC1)S(=O)(=O)C=2C=CC=CC=2)CCC)N1CC1=CC(Cl)=CC=C1OCC(O)=O SZXBYKZAJAJDDC-IBGZPJMESA-N 0.000 claims 1
- AUSHVDGRGPFHLF-HNNXBMFYSA-N 2-[2-[[(3S)-4-[2-(4-chlorophenyl)acetyl]-3-methylpiperazin-1-yl]methyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C=CC(Cl)=CC=2)C)N1CC1=CC(C(F)(F)F)=CC=C1OCC(O)=O AUSHVDGRGPFHLF-HNNXBMFYSA-N 0.000 claims 1
- TWPPHHVXBDKGSK-HNNXBMFYSA-N 2-[2-[[(3S)-4-[2-(4-fluorophenyl)acetyl]-3-methylpiperazin-1-yl]methyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C=CC(F)=CC=2)C)N1CC1=CC(C(F)(F)F)=CC=C1OCC(O)=O TWPPHHVXBDKGSK-HNNXBMFYSA-N 0.000 claims 1
- FLIBQBISMSABGY-UHFFFAOYSA-N 2-[2-[[4-(2-fluorophenyl)sulfonylpiperazin-1-yl]methyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1CN1CCN(S(=O)(=O)C=2C(=CC=CC=2)F)CC1 FLIBQBISMSABGY-UHFFFAOYSA-N 0.000 claims 1
- HAOLKUKLONSUFT-UHFFFAOYSA-N 2-[2-[[4-(2-methylphenyl)sulfonylpiperazin-1-yl]methyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound CC1=CC=CC=C1S(=O)(=O)N1CCN(CC=2C(=CC=C(C=2)C(F)(F)F)OCC(O)=O)CC1 HAOLKUKLONSUFT-UHFFFAOYSA-N 0.000 claims 1
- ULOFDAOEEZQONI-UHFFFAOYSA-N 2-[2-[[4-(2-phenylacetyl)piperazin-1-yl]methyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1CN1CCN(C(=O)CC=2C=CC=CC=2)CC1 ULOFDAOEEZQONI-UHFFFAOYSA-N 0.000 claims 1
- BZSFCWBYHPUSIP-UHFFFAOYSA-N 2-[2-[[4-(2-thiophen-2-ylacetyl)piperazin-1-yl]methyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1CN1CCN(C(=O)CC=2SC=CC=2)CC1 BZSFCWBYHPUSIP-UHFFFAOYSA-N 0.000 claims 1
- HBHJUOTUSQCINC-UHFFFAOYSA-N 2-[2-[[4-(4-cyanophenyl)sulfonyl-1,4-diazepan-1-yl]methyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1CN1CCN(S(=O)(=O)C=2C=CC(=CC=2)C#N)CCC1 HBHJUOTUSQCINC-UHFFFAOYSA-N 0.000 claims 1
- NICXRKSDXYULRK-UHFFFAOYSA-N 2-[2-[[4-(4-fluorophenyl)sulfonyl-1,4-diazepan-1-yl]methyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1CN1CCN(S(=O)(=O)C=2C=CC(F)=CC=2)CCC1 NICXRKSDXYULRK-UHFFFAOYSA-N 0.000 claims 1
- LSKNVKUQIOUJKU-UHFFFAOYSA-N 2-[2-[[4-(4-nitrophenyl)sulfonylpiperazin-1-yl]methyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1CN1CCN(S(=O)(=O)C=2C=CC(=CC=2)[N+]([O-])=O)CC1 LSKNVKUQIOUJKU-UHFFFAOYSA-N 0.000 claims 1
- QLFDFEFQMOQFGD-UHFFFAOYSA-N 2-[2-[[4-(benzenesulfonyl)-1,4-diazepan-1-yl]methyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C(F)(F)F)C=C1CN1CCN(S(=O)(=O)C=2C=CC=CC=2)CCC1 QLFDFEFQMOQFGD-UHFFFAOYSA-N 0.000 claims 1
- QPKLSOHWYXCVTB-UHFFFAOYSA-N 2-[2-[[4-(benzenesulfonyl)-1,4-diazepan-1-yl]methyl]-4-chlorophenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1CN1CCN(S(=O)(=O)C=2C=CC=CC=2)CCC1 QPKLSOHWYXCVTB-UHFFFAOYSA-N 0.000 claims 1
- KQVTZYFUHDWJOQ-UHFFFAOYSA-N 2-[2-[[4-(benzenesulfonyl)-2-methylpiperazin-1-yl]methyl]-4-chlorophenoxy]acetic acid Chemical compound CC1CN(S(=O)(=O)C=2C=CC=CC=2)CCN1CC1=CC(Cl)=CC=C1OCC(O)=O KQVTZYFUHDWJOQ-UHFFFAOYSA-N 0.000 claims 1
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- WIQVWABSIRJASR-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[3-(trifluoromethoxy)phenyl]sulfonylpiperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1CN1CCN(S(=O)(=O)C=2C=C(OC(F)(F)F)C=CC=2)CC1 WIQVWABSIRJASR-UHFFFAOYSA-N 0.000 claims 1
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| PT1817282E (pt) | 2004-11-23 | 2011-09-19 | Astrazeneca Ab | Derivados do ácido fenoxiacético úteis para tratar doenças respiratórias |
| RU2405770C2 (ru) * | 2005-09-27 | 2010-12-10 | Сионоги Энд Ко., Лтд. | Производное сульфонамида, обладающее антагонистической активностью в отношении рецептора pgd2 |
| SI1928457T1 (sl) * | 2005-09-30 | 2013-06-28 | Pulmagen Therapeutics (Asthma) Limited | Kuinolilni in njihova terapevtska raba |
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| US8148572B2 (en) | 2005-10-06 | 2012-04-03 | Astrazeneca Ab | Compounds |
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| 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 |
| SI2229358T1 (sl) | 2007-12-14 | 2011-10-28 | Pulmagen Therapeutics Asthma Ltd | Indoli in njihova terapevtska uporaba |
| BRPI0922880A2 (pt) * | 2008-12-09 | 2018-07-24 | Univ Florida | compostos inibidores de quinase |
| US8461078B2 (en) | 2009-01-14 | 2013-06-11 | Dow Agrosciences Llc | Fungicidal compositions including hydrazone derivatives and copper |
| RU2013104506A (ru) | 2010-07-05 | 2014-08-10 | Актелион Фармасьютиклз Лтд | 1-фенилзамещенные производные гетероциклила и их применение в качестве модуляторов рецептора простагландина d2 |
| EP2457900A1 (en) | 2010-11-25 | 2012-05-30 | Almirall, S.A. | New pyrazole derivatives having CRTh2 antagonistic behaviour |
| 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 |
| KR20140107550A (ko) | 2011-12-21 | 2014-09-04 | 액테리온 파마슈티칼 리미티드 | 헤테로시클릴 유도체 및 프로스타글란딘 ｄ2 수용체 조절제로서의 그의 용도 |
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| EP3288527B1 (en) | 2015-04-28 | 2020-02-19 | Unilever PLC, a company registered in England and Wales under company no. 41424 of | N-aralkylcarbonyldiamine compounds and personal care compositions comprising the same |
| CN107531655B (zh) | 2015-04-28 | 2021-03-12 | 荷兰联合利华有限公司 | N-芳烷基羰基-哌嗪和n-芳烷基羰基-高哌嗪化合物以及包含它们的个人护理组合物 |
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| 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 |
| IL152682A0 (en) | 2000-05-31 | 2003-06-24 | Astrazeneca Ab | Indole derivatives with vascular damaging activity |
| CN1245974C (zh) * | 2000-06-28 | 2006-03-22 | 特瓦制药工业有限公司 | 卡维地洛 |
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| 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 |
| ATE340792T1 (de) | 2002-02-01 | 2006-10-15 | Hoffmann La Roche | Substituierte indole als alpha-1 agonisten |
| SE0200411D0 (sv) | 2002-02-05 | 2002-02-05 | Astrazeneca Ab | Novel use |
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| US7119200B2 (en) * | 2002-09-04 | 2006-10-10 | Schering Corporation | Pyrazolopyrimidines as cyclin dependent kinase inhibitors |
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| PT1817282E (pt) | 2004-11-23 | 2011-09-19 | Astrazeneca Ab | Derivados do ácido fenoxiacético úteis para tratar doenças respiratórias |
| GB0510584D0 (en) | 2005-05-24 | 2005-06-29 | Novartis Ag | Organic compounds |
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| US8148572B2 (en) | 2005-10-06 | 2012-04-03 | Astrazeneca Ab | 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 |
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| UA100983C2 (ru) | 2007-07-05 | 2013-02-25 | Астразенека Аб | Бифенилоксипропановая кислота как модулятор crth2 и интермедиаты |
-
2005
- 2005-11-22 PT PT05807437T patent/PT1817282E/pt unknown
- 2005-11-22 PL PL05807437T patent/PL1817282T3/pl unknown
- 2005-11-22 SI SI200531361T patent/SI1817282T1/sl unknown
- 2005-11-22 AT AT05807437T patent/ATE517085T1/de active
- 2005-11-22 UY UY29223A patent/UY29223A1/es not_active Application Discontinuation
- 2005-11-22 US US11/719,832 patent/US8524715B2/en not_active Expired - Fee Related
- 2005-11-22 EP EP05807437A patent/EP1817282B1/en not_active Not-in-force
- 2005-11-22 WO PCT/GB2005/004464 patent/WO2006056752A1/en active Application Filing
- 2005-11-22 AR ARP050104896A patent/AR051966A1/es unknown
- 2005-11-22 DK DK05807437.8T patent/DK1817282T3/da active
- 2005-11-22 JP JP2007542103A patent/JP5208510B2/ja not_active Expired - Fee Related
- 2005-11-23 TW TW094141046A patent/TW200630336A/zh unknown
- 2005-11-23 SA SA05260362A patent/SA05260362B1/ar unknown
-
2011
- 2011-09-15 CY CY20111100891T patent/CY1112115T1/el unknown
-
2012
- 2012-12-21 JP JP2012280027A patent/JP2013082729A/ja active Pending
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