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
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- -1 C (O) R 9 Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004429 atom 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 atom 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
- 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
- 238000000034 method Methods 0.000 claims description 4
- 125000000882 C2-C6 alkenyl 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 8
- 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 4
- 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
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 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
- 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
- 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
- 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
- OVNWHOGUZJEKAS-UHFFFAOYSA-N 2-[2-[[4-(benzenesulfonyl)-3-methylpiperazin-1-yl]methyl]-4-chlorophenoxy]acetic acid Chemical compound C1CN(S(=O)(=O)C=2C=CC=CC=2)C(C)CN1CC1=CC(Cl)=CC=C1OCC(O)=O OVNWHOGUZJEKAS-UHFFFAOYSA-N 0.000 claims 1
- MNRULTNYMVKEMA-UHFFFAOYSA-N 2-[2-[[4-(benzenesulfonyl)piperazin-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)CC1 MNRULTNYMVKEMA-UHFFFAOYSA-N 0.000 claims 1
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- IAQXQPWNIYKQDL-SFHVURJKSA-N 2-[4-methyl-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(C)=CC=C1OCC(O)=O IAQXQPWNIYKQDL-SFHVURJKSA-N 0.000 claims 1
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| 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 |
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| US8993763B2 (en) | 2005-09-27 | 2015-03-31 | Shionogi & Co., Ltd. | Sulfonamide derivative having PGD2 receptor antagonistic activity |
| PL1928457T3 (pl) * | 2005-09-30 | 2013-04-30 | Pulmagen Therapeutics Asthma Ltd | Chinoliny i ich zastosowanie terapeutyczne |
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| US20080255150A1 (en) * | 2005-11-05 | 2008-10-16 | 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 |
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| US20110301159A1 (en) * | 2008-12-09 | 2011-12-08 | University Of South Florida | Kinase inhibitor compounds |
| WO2010083318A2 (en) | 2009-01-14 | 2010-07-22 | Dow Agrosciences Llc | Fungicidal compositions including hydrazone derivatives and copper |
| EP2590944B1 (en) | 2010-07-05 | 2015-09-30 | Actelion Pharmaceuticals Ltd. | 1-phenyl-substituted heterocyclyl derivatives and their use as prostaglandin d2 receptor modulators |
| EP2457900A1 (en) | 2010-11-25 | 2012-05-30 | Almirall, S.A. | New pyrazole derivatives having CRTh2 antagonistic behaviour |
| 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 |
| US9255090B2 (en) | 2011-12-21 | 2016-02-09 | Actelion Pharmaceuticals Ltd. | Heterocyclyl derivatives and their use as prostaglandin D2 receptor modulators |
| US9169270B2 (en) | 2012-07-05 | 2015-10-27 | Actelion Pharmaceuticals Ltd. | 1-phenyl-substituted heterocyclyl derivatives and their use as prostaglandin D2 receptor modulators |
| WO2016173817A1 (en) | 2015-04-28 | 2016-11-03 | Unilever Plc | N-aralkylcarbonyl-piperazine and -homopiperazine compounds and personal care compositions comprising the same |
| US10307355B2 (en) | 2015-04-28 | 2019-06-04 | Conopco, Inc. | N-aralkylcarbonyldiamine compounds and personal care compositions comprising the same |
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-
2005
- 2005-11-22 UY UY29223A patent/UY29223A1/es not_active Application Discontinuation
- 2005-11-22 WO PCT/GB2005/004464 patent/WO2006056752A1/en not_active Ceased
- 2005-11-22 PT PT05807437T patent/PT1817282E/pt unknown
- 2005-11-22 DK DK05807437.8T patent/DK1817282T3/da active
- 2005-11-22 AR ARP050104896A patent/AR051966A1/es unknown
- 2005-11-22 PL PL05807437T patent/PL1817282T3/pl unknown
- 2005-11-22 EP EP05807437A patent/EP1817282B1/en not_active Expired - Lifetime
- 2005-11-22 JP JP2007542103A patent/JP5208510B2/ja not_active Expired - Fee Related
- 2005-11-22 SI SI200531361T patent/SI1817282T1/sl unknown
- 2005-11-22 AT AT05807437T patent/ATE517085T1/de active
- 2005-11-22 US US11/719,832 patent/US8524715B2/en 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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