JP2008520637A5 - - Google Patents

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Publication number: JP2008520637A5
Authority: JP; Japan
Prior art keywords: methyl; phenoxy; piperazinyl; acetic acid; chloro
Prior art date: 2005-11-22
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

Application number

JP2007542103A

Other languages

English (en)

Japanese (ja)

Other versions

JP5208510B2 (ja

JP2008520637A (ja

Filing date

2005-11-22

Publication date

2009-01-15

2004-11-23 Priority claimed from GB0425673A external-priority patent/GB0425673D0/en

2005-04-30 Priority claimed from GB0508923A external-priority patent/GB0508923D0/en

2005-11-22 Application filed filed Critical

2005-11-22 Priority claimed from PCT/GB2005/004464 external-priority patent/WO2006056752A1/en

2008-06-19 Publication of JP2008520637A publication Critical patent/JP2008520637A/ja

2009-01-15 Publication of JP2008520637A5 publication Critical patent/JP2008520637A5/ja

2013-06-12 Application granted granted Critical

2013-06-12 Publication of JP5208510B2 publication Critical patent/JP5208510B2/ja

2025-11-22 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

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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
SNWISXHDGOBZCF-UHFFFAOYSA-N 2-[2-[[4-(benzenesulfonyl)piperazin-1-yl]methyl]-4-fluorophenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(F)C=C1CN1CCN(S(=O)(=O)C=2C=CC=CC=2)CC1 SNWISXHDGOBZCF-UHFFFAOYSA-N 0.000 claims 1
COQXOABONQWPHS-UHFFFAOYSA-N 2-[2-[[4-(benzenesulfonyl)piperazin-1-yl]methyl]-4-propan-2-ylphenoxy]acetic acid Chemical compound CC(C)C1=CC=C(OCC(O)=O)C(CN2CCN(CC2)S(=O)(=O)C=2C=CC=CC=2)=C1 COQXOABONQWPHS-UHFFFAOYSA-N 0.000 claims 1
ZMNFGTRQTBDMOW-UHFFFAOYSA-N 2-[2-[[[1-(benzenesulfonyl)pyrrolidin-3-yl]-methylamino]methyl]-4-chlorophenoxy]acetic acid Chemical compound C1CN(S(=O)(=O)C=2C=CC=CC=2)CC1N(C)CC1=CC(Cl)=CC=C1OCC(O)=O ZMNFGTRQTBDMOW-UHFFFAOYSA-N 0.000 claims 1
DJERRLOJXBPOPO-UHFFFAOYSA-N 2-[2-[[[1-(benzenesulfonyl)pyrrolidin-3-yl]amino]methyl]-4-chlorophenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1CNC1CN(S(=O)(=O)C=2C=CC=CC=2)CC1 DJERRLOJXBPOPO-UHFFFAOYSA-N 0.000 claims 1
KTAAWZKEPNPWTK-UHFFFAOYSA-N 2-[3-chloro-2-[[4-[2-(4-chlorophenyl)acetyl]piperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=CC(Cl)=C1CN1CCN(C(=O)CC=2C=CC(Cl)=CC=2)CC1 KTAAWZKEPNPWTK-UHFFFAOYSA-N 0.000 claims 1
HXEJGACBYOEVOX-HNNXBMFYSA-N 2-[3-methyl-2-[(3s)-3-methyl-4-(2-phenylacetyl)piperazin-1-yl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound C([C@@H]1C)N(C=2C(=CC=C(C=2C)C(F)(F)F)OCC(O)=O)CCN1C(=O)CC1=CC=CC=C1 HXEJGACBYOEVOX-HNNXBMFYSA-N 0.000 claims 1
KZWUJVNNRAMFCJ-UHFFFAOYSA-N 2-[4-chloro-2-[4-(2-phenylacetyl)piperazin-1-yl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1N1CCN(C(=O)CC=2C=CC=CC=2)CC1 KZWUJVNNRAMFCJ-UHFFFAOYSA-N 0.000 claims 1
GMFBGMFMMAVODH-MRXNPFEDSA-N 2-[4-chloro-2-[[(3r)-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-MRXNPFEDSA-N 0.000 claims 1
WPTNBMSBMRYYKO-FQEVSTJZSA-N 2-[4-chloro-2-[[(3s)-3-ethyl-4-(2-phenylacetyl)piperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C=CC=CC=2)CC)N1CC1=CC(Cl)=CC=C1OCC(O)=O WPTNBMSBMRYYKO-FQEVSTJZSA-N 0.000 claims 1
YUXPRRHTMUOHMI-KRWDZBQOSA-N 2-[4-chloro-2-[[(3s)-3-methyl-4-[2-(4-methylphenyl)acetyl]piperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C=CC(C)=CC=2)C)N1CC1=CC(Cl)=CC=C1OCC(O)=O YUXPRRHTMUOHMI-KRWDZBQOSA-N 0.000 claims 1
VIFCTABXRRMWCE-HNNXBMFYSA-N 2-[4-chloro-2-[[(3s)-3-methyl-4-[2-[4-(trifluoromethoxy)phenyl]acetyl]piperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C=CC(OC(F)(F)F)=CC=2)C)N1CC1=CC(Cl)=CC=C1OCC(O)=O VIFCTABXRRMWCE-HNNXBMFYSA-N 0.000 claims 1
ULQJVTFUHXKALQ-HNNXBMFYSA-N 2-[4-chloro-2-[[(3s)-3-methyl-4-[2-[4-(trifluoromethyl)phenyl]acetyl]piperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C=CC(=CC=2)C(F)(F)F)C)N1CC1=CC(Cl)=CC=C1OCC(O)=O ULQJVTFUHXKALQ-HNNXBMFYSA-N 0.000 claims 1
PFXOFTISOIWABY-OAQYLSRUSA-N 2-[4-chloro-2-[[(3s)-4-(2-phenylacetyl)-3-propan-2-ylpiperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C=CC=CC=2)C(C)C)N1CC1=CC(Cl)=CC=C1OCC(O)=O PFXOFTISOIWABY-OAQYLSRUSA-N 0.000 claims 1
LRZJRQDAHZPEFU-NRFANRHFSA-N 2-[4-chloro-2-[[(3s)-4-(2-phenylacetyl)-3-propylpiperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C=CC=CC=2)CCC)N1CC1=CC(Cl)=CC=C1OCC(O)=O LRZJRQDAHZPEFU-NRFANRHFSA-N 0.000 claims 1
LVRRECMHGPOQTQ-AWEZNQCLSA-N 2-[4-chloro-2-[[(3s)-4-[2-(2,4-dichlorophenyl)acetyl]-3-methylpiperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C(=CC(Cl)=CC=2)Cl)C)N1CC1=CC(Cl)=CC=C1OCC(O)=O LVRRECMHGPOQTQ-AWEZNQCLSA-N 0.000 claims 1
QGRXYDKCNSWGEB-AWEZNQCLSA-N 2-[4-chloro-2-[[(3s)-4-[2-(2,4-difluorophenyl)acetyl]-3-methylpiperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C(=CC(F)=CC=2)F)C)N1CC1=CC(Cl)=CC=C1OCC(O)=O QGRXYDKCNSWGEB-AWEZNQCLSA-N 0.000 claims 1
KVMMUHZNDVGFAI-HNNXBMFYSA-N 2-[4-chloro-2-[[(3s)-4-[2-(2-chlorophenyl)acetyl]-3-methylpiperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C(=CC=CC=2)Cl)C)N1CC1=CC(Cl)=CC=C1OCC(O)=O KVMMUHZNDVGFAI-HNNXBMFYSA-N 0.000 claims 1
BRNHNKARNMEPCH-AWEZNQCLSA-N 2-[4-chloro-2-[[(3s)-4-[2-(3,4-dichlorophenyl)acetyl]-3-methylpiperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C=C(Cl)C(Cl)=CC=2)C)N1CC1=CC(Cl)=CC=C1OCC(O)=O BRNHNKARNMEPCH-AWEZNQCLSA-N 0.000 claims 1
AKGCSSSQGMHLQE-HNNXBMFYSA-N 2-[4-chloro-2-[[(3s)-4-[2-(3-chlorophenyl)acetyl]-3-methylpiperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C=C(Cl)C=CC=2)C)N1CC1=CC(Cl)=CC=C1OCC(O)=O AKGCSSSQGMHLQE-HNNXBMFYSA-N 0.000 claims 1
UMUOBHUONSSGBG-INIZCTEOSA-N 2-[4-chloro-2-[[(3s)-4-[2-(3-fluoro-4-methylphenyl)acetyl]-3-methylpiperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C=C(F)C(C)=CC=2)C)N1CC1=CC(Cl)=CC=C1OCC(O)=O UMUOBHUONSSGBG-INIZCTEOSA-N 0.000 claims 1
NRJBFDZWXPHYJR-HNNXBMFYSA-N 2-[4-chloro-2-[[(3s)-4-[2-(3-fluorophenyl)acetyl]-3-methylpiperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C=C(F)C=CC=2)C)N1CC1=CC(Cl)=CC=C1OCC(O)=O NRJBFDZWXPHYJR-HNNXBMFYSA-N 0.000 claims 1
VVYXFODKAOCOFT-AWEZNQCLSA-N 2-[4-chloro-2-[[(3s)-4-[2-(4-chloro-2-fluorophenyl)acetyl]-3-methylpiperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C(=CC(Cl)=CC=2)F)C)N1CC1=CC(Cl)=CC=C1OCC(O)=O VVYXFODKAOCOFT-AWEZNQCLSA-N 0.000 claims 1
MSSLADGIBICRTQ-INIZCTEOSA-N 2-[4-chloro-2-[[(3s)-4-[2-(4-chlorophenyl)-2-methylpropanoyl]-3-methylpiperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)C(C)(C)C=2C=CC(Cl)=CC=2)C)N1CC1=CC(Cl)=CC=C1OCC(O)=O MSSLADGIBICRTQ-INIZCTEOSA-N 0.000 claims 1
BHZNGMOMDQDTGT-HNNXBMFYSA-N 2-[4-chloro-2-[[(3s)-4-[2-(4-chlorophenyl)acetyl]-3-methylpiperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C=CC(Cl)=CC=2)C)N1CC1=CC(Cl)=CC=C1OCC(O)=O BHZNGMOMDQDTGT-HNNXBMFYSA-N 0.000 claims 1
HETDCNLHSCWGNG-HNNXBMFYSA-N 2-[4-chloro-2-[[(3s)-4-[2-(4-fluorophenyl)acetyl]-3-methylpiperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C=CC(F)=CC=2)C)N1CC1=CC(Cl)=CC=C1OCC(O)=O HETDCNLHSCWGNG-HNNXBMFYSA-N 0.000 claims 1
UIEALAUEQXQKKJ-INIZCTEOSA-N 2-[4-chloro-2-[[(3s)-4-[2-(4-methoxyphenyl)acetyl]-3-methylpiperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound C1=CC(OC)=CC=C1CC(=O)N1[C@@H](C)CN(CC=2C(=CC=C(Cl)C=2)OCC(O)=O)CC1 UIEALAUEQXQKKJ-INIZCTEOSA-N 0.000 claims 1
KPCVQXUUGXXCCD-AWEZNQCLSA-N 2-[4-chloro-2-[[(3s)-4-[2-[2-fluoro-4-(trifluoromethyl)phenyl]acetyl]-3-methylpiperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C(=CC(=CC=2)C(F)(F)F)F)C)N1CC1=CC(Cl)=CC=C1OCC(O)=O KPCVQXUUGXXCCD-AWEZNQCLSA-N 0.000 claims 1
DHPMQWCGCDLZMZ-AWEZNQCLSA-N 2-[4-chloro-2-[[(3s)-4-[2-[3-fluoro-4-(trifluoromethyl)phenyl]acetyl]-3-methylpiperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound C([C@@H](N(CC1)C(=O)CC=2C=C(F)C(=CC=2)C(F)(F)F)C)N1CC1=CC(Cl)=CC=C1OCC(O)=O DHPMQWCGCDLZMZ-AWEZNQCLSA-N 0.000 claims 1
AFHZNYOZSHABDK-CALCHBBNSA-N 2-[4-chloro-2-[[(3s,5r)-3,5-dimethyl-4-(2-phenylacetyl)piperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound C([C@@H](N([C@H](C)C1)C(=O)CC=2C=CC=CC=2)C)N1CC1=CC(Cl)=CC=C1OCC(O)=O AFHZNYOZSHABDK-CALCHBBNSA-N 0.000 claims 1
JTNMVEBSCUDNMB-UHFFFAOYSA-N 2-[4-chloro-2-[[2,5-dimethyl-4-(2-phenylacetyl)piperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound CC1CN(C(=O)CC=2C=CC=CC=2)C(C)CN1CC1=CC(Cl)=CC=C1OCC(O)=O JTNMVEBSCUDNMB-UHFFFAOYSA-N 0.000 claims 1
GMFBGMFMMAVODH-UHFFFAOYSA-N 2-[4-chloro-2-[[3-methyl-4-(2-phenylacetyl)piperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound C1CN(C(=O)CC=2C=CC=CC=2)C(C)CN1CC1=CC(Cl)=CC=C1OCC(O)=O GMFBGMFMMAVODH-UHFFFAOYSA-N 0.000 claims 1
QMELTJDCTLMGCP-UHFFFAOYSA-N 2-[4-chloro-2-[[4-(2-phenylacetyl)-1,4-diazepan-1-yl]methyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1CN1CCN(C(=O)CC=2C=CC=CC=2)CCC1 QMELTJDCTLMGCP-UHFFFAOYSA-N 0.000 claims 1
NZMAJXVEGBZEEC-UHFFFAOYSA-N 2-[4-chloro-2-[[4-(2-phenylpropanoyl)piperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound C=1C=CC=CC=1C(C)C(=O)N(CC1)CCN1CC1=CC(Cl)=CC=C1OCC(O)=O NZMAJXVEGBZEEC-UHFFFAOYSA-N 0.000 claims 1
LFQMJSQLJKPHCR-UHFFFAOYSA-N 2-[4-chloro-2-[[4-(2-pyridin-3-ylacetyl)piperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1CN1CCN(C(=O)CC=2C=NC=CC=2)CC1 LFQMJSQLJKPHCR-UHFFFAOYSA-N 0.000 claims 1
UGHQMGMBAHIYMH-UHFFFAOYSA-N 2-[4-chloro-2-[[4-(3,4-dichlorophenyl)sulfonylpiperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1CN1CCN(S(=O)(=O)C=2C=C(Cl)C(Cl)=CC=2)CC1 UGHQMGMBAHIYMH-UHFFFAOYSA-N 0.000 claims 1
IAPIBKHPGNYMIM-UHFFFAOYSA-N 2-[4-chloro-2-[[4-(3,4-difluorophenyl)sulfonylpiperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1CN1CCN(S(=O)(=O)C=2C=C(F)C(F)=CC=2)CC1 IAPIBKHPGNYMIM-UHFFFAOYSA-N 0.000 claims 1
QMYOIVSLXDKWKJ-UHFFFAOYSA-N 2-[4-chloro-2-[[4-(3-chloro-4-fluorophenyl)sulfonylpiperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1CN1CCN(S(=O)(=O)C=2C=C(Cl)C(F)=CC=2)CC1 QMYOIVSLXDKWKJ-UHFFFAOYSA-N 0.000 claims 1
HFLNBDKNUXVONC-UHFFFAOYSA-N 2-[4-chloro-2-[[4-(3-chlorophenyl)sulfonylpiperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1CN1CCN(S(=O)(=O)C=2C=C(Cl)C=CC=2)CC1 HFLNBDKNUXVONC-UHFFFAOYSA-N 0.000 claims 1
ZCMJPFSXDXFBES-UHFFFAOYSA-N 2-[4-chloro-2-[[4-(3-fluorophenyl)sulfonylpiperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1CN1CCN(S(=O)(=O)C=2C=C(F)C=CC=2)CC1 ZCMJPFSXDXFBES-UHFFFAOYSA-N 0.000 claims 1
HXEHNYOADQYQOC-UHFFFAOYSA-N 2-[4-chloro-2-[[4-(3-phenylpropanoyl)piperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1CN1CCN(C(=O)CCC=2C=CC=CC=2)CC1 HXEHNYOADQYQOC-UHFFFAOYSA-N 0.000 claims 1
MJFMIEXSNLSKBA-UHFFFAOYSA-N 2-[4-chloro-2-[[4-(4-chlorophenyl)sulfonylpiperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1CN1CCN(S(=O)(=O)C=2C=CC(Cl)=CC=2)CC1 MJFMIEXSNLSKBA-UHFFFAOYSA-N 0.000 claims 1
YEPKGHKIZDVJEY-UHFFFAOYSA-N 2-[4-chloro-2-[[4-(4-fluorophenyl)sulfonylpiperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1CN1CCN(S(=O)(=O)C=2C=CC(F)=CC=2)CC1 YEPKGHKIZDVJEY-UHFFFAOYSA-N 0.000 claims 1
SVKSSVSQZRWBMW-UHFFFAOYSA-N 2-[4-chloro-2-[[4-(pyridin-2-ylmethylsulfonyl)piperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1CN1CCN(S(=O)(=O)CC=2N=CC=CC=2)CC1 SVKSSVSQZRWBMW-UHFFFAOYSA-N 0.000 claims 1
MFNQNQUCCFZGBC-UHFFFAOYSA-N 2-[4-chloro-2-[[4-(pyridin-3-ylmethylsulfonyl)piperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1CN1CCN(S(=O)(=O)CC=2C=NC=CC=2)CC1 MFNQNQUCCFZGBC-UHFFFAOYSA-N 0.000 claims 1
HJYFIAQSJJSCJD-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[(2-nitrophenyl)methylsulfonyl]piperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1CN1CCN(S(=O)(=O)CC=2C(=CC=CC=2)[N+]([O-])=O)CC1 HJYFIAQSJJSCJD-UHFFFAOYSA-N 0.000 claims 1
TVAOVFSSAKYBGM-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[(3-chlorophenyl)methylsulfonyl]piperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1CN1CCN(S(=O)(=O)CC=2C=C(Cl)C=CC=2)CC1 TVAOVFSSAKYBGM-UHFFFAOYSA-N 0.000 claims 1
JQZCNXVAHYQALK-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[(3-methylphenyl)methylsulfonyl]piperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound CC1=CC=CC(CS(=O)(=O)N2CCN(CC=3C(=CC=C(Cl)C=3)OCC(O)=O)CC2)=C1 JQZCNXVAHYQALK-UHFFFAOYSA-N 0.000 claims 1
CWVJXMDXAIQPKJ-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[(4-chlorophenyl)methylsulfonyl]piperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1CN1CCN(S(=O)(=O)CC=2C=CC(Cl)=CC=2)CC1 CWVJXMDXAIQPKJ-UHFFFAOYSA-N 0.000 claims 1
QDSPXLFDGHZUJJ-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[(4-fluorophenyl)methylsulfonyl]piperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1CN1CCN(S(=O)(=O)CC=2C=CC(F)=CC=2)CC1 QDSPXLFDGHZUJJ-UHFFFAOYSA-N 0.000 claims 1
IOTNAJLLTFNQOL-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[(4-methylphenyl)methylsulfonyl]piperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound C1=CC(C)=CC=C1CS(=O)(=O)N1CCN(CC=2C(=CC=C(Cl)C=2)OCC(O)=O)CC1 IOTNAJLLTFNQOL-UHFFFAOYSA-N 0.000 claims 1
ULYCVFZPMWVYCG-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[2-(4-chlorophenyl)acetyl]piperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1CN1CCN(C(=O)CC=2C=CC(Cl)=CC=2)CC1 ULYCVFZPMWVYCG-UHFFFAOYSA-N 0.000 claims 1
GESQXXWZMKUSRO-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[2-(4-cyanophenyl)acetyl]piperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1CN1CCN(C(=O)CC=2C=CC(=CC=2)C#N)CC1 GESQXXWZMKUSRO-UHFFFAOYSA-N 0.000 claims 1
JKYOGZWGUBGRIF-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[2-(4-fluorophenyl)acetyl]piperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1CN1CCN(C(=O)CC=2C=CC(F)=CC=2)CC1 JKYOGZWGUBGRIF-UHFFFAOYSA-N 0.000 claims 1
SYNYMOOIHRQYQN-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[2-(4-methoxyphenyl)acetyl]piperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound C1=CC(OC)=CC=C1CC(=O)N1CCN(CC=2C(=CC=C(Cl)C=2)OCC(O)=O)CC1 SYNYMOOIHRQYQN-UHFFFAOYSA-N 0.000 claims 1
YFJRJSADALDRPD-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[2-(4-methylphenyl)acetyl]piperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound C1=CC(C)=CC=C1CC(=O)N1CCN(CC=2C(=CC=C(Cl)C=2)OCC(O)=O)CC1 YFJRJSADALDRPD-UHFFFAOYSA-N 0.000 claims 1
CWVWNDSQBGNNDK-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[3-(difluoromethoxy)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)C=CC=2)CC1 CWVWNDSQBGNNDK-UHFFFAOYSA-N 0.000 claims 1
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
QDMXZTDDAPAHGD-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[3-(trifluoromethyl)phenyl]sulfonylpiperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1CN1CCN(S(=O)(=O)C=2C=C(C=CC=2)C(F)(F)F)CC1 QDMXZTDDAPAHGD-UHFFFAOYSA-N 0.000 claims 1
SKIALVHXEPTEDB-KRWDZBQOSA-N 2-[4-cyano-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#N)=CC=C1OCC(O)=O SKIALVHXEPTEDB-KRWDZBQOSA-N 0.000 claims 1
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
NUUKCZHOQCNSMN-UHFFFAOYSA-N 2-[6-chloro-6-[[4-[2-(4-chlorophenyl)acetyl]piperazin-1-yl]methyl]cyclohexa-2,4-dien-1-yl]oxyacetic acid Chemical compound OC(=O)COC1C=CC=CC1(Cl)CN1CCN(C(=O)CC=2C=CC(Cl)=CC=2)CC1 NUUKCZHOQCNSMN-UHFFFAOYSA-N 0.000 claims 1
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
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WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims 1
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208000006673 asthma Diseases 0.000 claims 1
BDIIXJCOXLQTKD-UHFFFAOYSA-N azetidin-1-amine Chemical compound NN1CCC1 BDIIXJCOXLQTKD-UHFFFAOYSA-N 0.000 claims 1
150000004985 diamines Chemical class 0.000 claims 1
VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 claims 1
230000001404 mediated effect Effects 0.000 claims 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims 1
LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 claims 1
150000003053 piperidines Chemical class 0.000 claims 1
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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 1
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208000023504 respiratory system disease Diseases 0.000 claims 1
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VXVIICNFYDEOJG-UHFFFAOYSA-N 2-(4-chloro-2-formylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1C=O VXVIICNFYDEOJG-UHFFFAOYSA-N 0.000 description 1
GGXHNHALEKSOAT-UHFFFAOYSA-N 2-(4-chloro-2-piperazin-1-ylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1N1CCNCC1 GGXHNHALEKSOAT-UHFFFAOYSA-N 0.000 description 1
ZOUYZUHVCHDANN-UHFFFAOYSA-N 2-[4-chloro-2-(piperazin-1-ylmethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1CN1CCNCC1 ZOUYZUHVCHDANN-UHFFFAOYSA-N 0.000 description 1
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YVCIXOUQKBWCPW-UHFFFAOYSA-N Cl.OC1=CC=C(Cl)C=C1N1CCNCC1.COC1=CC=C(Cl)C=C1N1CCNCC1 Chemical compound Cl.OC1=CC=C(Cl)C=C1N1CCNCC1.COC1=CC=C(Cl)C=C1N1CCNCC1 YVCIXOUQKBWCPW-UHFFFAOYSA-N 0.000 description 1
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ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
RCBWGBZOCSJUEI-UHFFFAOYSA-N [1-(benzenesulfonyl)pyrrolidin-3-yl]-methylcarbamic acid Chemical compound C1C(N(C)C(O)=O)CCN1S(=O)(=O)C1=CC=CC=C1 RCBWGBZOCSJUEI-UHFFFAOYSA-N 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
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INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
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239000011541 reaction mixture Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
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239000000725 suspension Substances 0.000 description 1
FMLPQHJYUZTHQS-QMMMGPOBSA-N tert-butyl (3s)-3-methylpiperazine-1-carboxylate Chemical compound C[C@H]1CN(C(=O)OC(C)(C)C)CCN1 FMLPQHJYUZTHQS-QMMMGPOBSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1

JP2007542103A 2004-11-23 2005-11-22 呼吸器疾患の処置に有用なフェノキシ酢酸誘導体 Expired - Fee Related JP5208510B2 (ja)

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2005
- 2005-11-22 UY UY29223A patent/UY29223A1/es not_active Application Discontinuation
- 2005-11-22 SI SI200531361T patent/SI1817282T1/sl unknown
- 2005-11-22 AT AT05807437T patent/ATE517085T1/de active
- 2005-11-22 EP EP05807437A patent/EP1817282B1/en not_active Expired - Lifetime
- 2005-11-22 AR ARP050104896A patent/AR051966A1/es unknown
- 2005-11-22 PT PT05807437T patent/PT1817282E/pt unknown
- 2005-11-22 PL PL05807437T patent/PL1817282T3/pl unknown
- 2005-11-22 US US11/719,832 patent/US8524715B2/en not_active Expired - Fee Related
- 2005-11-22 WO PCT/GB2005/004464 patent/WO2006056752A1/en not_active Ceased
- 2005-11-22 JP JP2007542103A patent/JP5208510B2/ja not_active Expired - Fee Related
- 2005-11-22 DK DK05807437.8T patent/DK1817282T3/da active
- 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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