HRP20100148T1 - Antagonisti glukagonskog receptora, priprema i terapijska primjena - Google Patents
Antagonisti glukagonskog receptora, priprema i terapijska primjena Download PDFInfo
- Publication number
- HRP20100148T1 HRP20100148T1 HR20100148T HRP20100148T HRP20100148T1 HR P20100148 T1 HRP20100148 T1 HR P20100148T1 HR 20100148 T HR20100148 T HR 20100148T HR P20100148 T HRP20100148 T HR P20100148T HR P20100148 T1 HRP20100148 T1 HR P20100148T1
- Authority
- HR
- Croatia
- Prior art keywords
- benzoylamino
- propionic acid
- yloxy
- biphenyl
- butyl
- Prior art date
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- 229940122904 Glucagon receptor antagonist Drugs 0.000 title abstract 2
- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 28
- 150000003839 salts Chemical class 0.000 claims abstract 20
- 102000051325 Glucagon Human genes 0.000 claims abstract 2
- 108060003199 Glucagon Proteins 0.000 claims abstract 2
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract 2
- MASNOZXLGMXCHN-ZLPAWPGGSA-N glucagon Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 MASNOZXLGMXCHN-ZLPAWPGGSA-N 0.000 claims abstract 2
- 229960004666 glucagon Drugs 0.000 claims abstract 2
- 208000030159 metabolic disease Diseases 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims 52
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 47
- 150000002367 halogens Chemical class 0.000 claims 37
- 229910052757 nitrogen Inorganic materials 0.000 claims 32
- 239000001257 hydrogen Substances 0.000 claims 31
- 229910052739 hydrogen Inorganic materials 0.000 claims 31
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 20
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 19
- -1 1,3-dioxan-2-yl Chemical group 0.000 claims 16
- 125000001424 substituent group Chemical group 0.000 claims 13
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- 125000003342 alkenyl group Chemical group 0.000 claims 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 9
- 229910052799 carbon Inorganic materials 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- CNEOYRMDNHRHPN-UHFFFAOYSA-N 2-hydroxy-3-[[4-[1-[4-[4-(trifluoromethyl)phenyl]phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCC(O)C(O)=O)C=CC=1C(CCCCCC)OC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 CNEOYRMDNHRHPN-UHFFFAOYSA-N 0.000 claims 6
- WSPPXWCAPCGQJQ-UHFFFAOYSA-N 3-[[4-[1-(4-tert-butylphenoxy)-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC1=CC=C(C(C)(C)C)C=C1 WSPPXWCAPCGQJQ-UHFFFAOYSA-N 0.000 claims 6
- FIYNEGAABIBBTB-UHFFFAOYSA-N 3-[[4-[1-[(2,2,3,3-tetrafluoro-1,4-benzodioxin-6-yl)oxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C2OC(F)(F)C(F)(F)OC2=CC=1OC(CCCCCC)C1=CC=C(C(=O)NCCC(O)=O)C=C1 FIYNEGAABIBBTB-UHFFFAOYSA-N 0.000 claims 6
- IWGBSYIRRQHWIL-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)-3,5-dimethylphenoxy]-3,3-dimethylbutyl]benzoyl]amino]-2-hydroxypropanoic acid Chemical compound C=1C(C)=C(C=2C=CC(=CC=2)C(C)(C)C)C(C)=CC=1OC(CC(C)(C)C)C1=CC=C(C(=O)NCC(O)C(O)=O)C=C1 IWGBSYIRRQHWIL-UHFFFAOYSA-N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000001475 halogen functional group Chemical group 0.000 claims 6
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- ALKVRMGAYOQIGX-UHFFFAOYSA-N 3-[[4-[1-[3,5-dimethyl-4-(4-propan-2-ylphenyl)phenoxy]-2-methylpropyl]benzoyl]amino]-2-hydroxypropanoic acid Chemical compound C=1C=C(C(=O)NCC(O)C(O)=O)C=CC=1C(C(C)C)OC(C=C1C)=CC(C)=C1C1=CC=C(C(C)C)C=C1 ALKVRMGAYOQIGX-UHFFFAOYSA-N 0.000 claims 4
- PRJBNBMSKZJJFV-UHFFFAOYSA-N 3-[[4-[1-[3,5-dimethyl-4-[4-(trifluoromethyl)phenyl]phenoxy]-2-methylpropyl]benzoyl]amino]-2-hydroxypropanoic acid Chemical compound C=1C=C(C(=O)NCC(O)C(O)=O)C=CC=1C(C(C)C)OC(C=C1C)=CC(C)=C1C1=CC=C(C(F)(F)F)C=C1 PRJBNBMSKZJJFV-UHFFFAOYSA-N 0.000 claims 4
- YIRJYWUBDGOMAF-UHFFFAOYSA-N 3-[[4-[1-[3,5-dimethyl-4-[4-(trifluoromethyl)phenyl]phenoxy]-4,4-dimethylpentyl]benzoyl]amino]propanoic acid Chemical compound C=1C(C)=C(C=2C=CC(=CC=2)C(F)(F)F)C(C)=CC=1OC(CCC(C)(C)C)C1=CC=C(C(=O)NCCC(O)=O)C=C1 YIRJYWUBDGOMAF-UHFFFAOYSA-N 0.000 claims 4
- COXXDQWZBMCHRT-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)-3,5-dimethylphenoxy]-2-methylpropyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(C(C)C)OC(C=C1C)=CC(C)=C1C1=CC=C(C(C)(C)C)C=C1 COXXDQWZBMCHRT-UHFFFAOYSA-N 0.000 claims 4
- FASLTMSUPQDLIB-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)-3,5-dimethylphenoxy]-4,4,4-trifluorobutyl]benzoyl]amino]propanoic acid Chemical compound C=1C(C)=C(C=2C=CC(=CC=2)C(C)(C)C)C(C)=CC=1OC(CCC(F)(F)F)C1=CC=C(C(=O)NCCC(O)=O)C=C1 FASLTMSUPQDLIB-UHFFFAOYSA-N 0.000 claims 4
- 125000000439 4-methylpentoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 3
- HSLOTHSWKXHUIO-UHFFFAOYSA-N 3-[[3-fluoro-4-[1-[3-methyl-4-[4-(trifluoromethyl)phenyl]phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=C(F)C=1C(CCCCCC)OC(C=C1C)=CC=C1C1=CC=C(C(F)(F)F)C=C1 HSLOTHSWKXHUIO-UHFFFAOYSA-N 0.000 claims 3
- OHGRKGYWSFIXGP-UHFFFAOYSA-N 3-[[3-fluoro-4-[3-methyl-1-[6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]oxybutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=C(F)C=1C(CC(C)C)OC(C=N1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 OHGRKGYWSFIXGP-UHFFFAOYSA-N 0.000 claims 3
- XUWCKRGDJUUNCD-UHFFFAOYSA-N 3-[[4-[1-(3,5-dimethyl-4-phenylphenoxy)-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=C1C)=CC(C)=C1C1=CC=CC=C1 XUWCKRGDJUUNCD-UHFFFAOYSA-N 0.000 claims 3
- UOZNCBXVTQLAFF-UHFFFAOYSA-N 3-[[4-[1-(4-phenylmethoxyphenoxy)hexyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCC)OC(C=C1)=CC=C1OCC1=CC=CC=C1 UOZNCBXVTQLAFF-UHFFFAOYSA-N 0.000 claims 3
- KJYDPCNTADRITI-UHFFFAOYSA-N 3-[[4-[1-[3,5-dimethyl-4-(4-propan-2-ylphenyl)phenoxy]-2-methylpropyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(C(C)C)OC(C=C1C)=CC(C)=C1C1=CC=C(C(C)C)C=C1 KJYDPCNTADRITI-UHFFFAOYSA-N 0.000 claims 3
- INPNTERYXTZXCO-UHFFFAOYSA-N 3-[[4-[1-[3,5-dimethyl-4-(4-propan-2-ylphenyl)phenoxy]-4,4,4-trifluorobutyl]benzoyl]amino]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1C(C(=C1)C)=C(C)C=C1OC(CCC(F)(F)F)C1=CC=C(C(=O)NCCC(O)=O)C=C1 INPNTERYXTZXCO-UHFFFAOYSA-N 0.000 claims 3
- WJQZKZZBMOZYMN-UHFFFAOYSA-N 3-[[4-[1-[3,5-dimethyl-4-(4-propan-2-ylphenyl)phenoxy]-4,4-dimethylpentyl]benzoyl]amino]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1C(C(=C1)C)=C(C)C=C1OC(CCC(C)(C)C)C1=CC=C(C(=O)NCCC(O)=O)C=C1 WJQZKZZBMOZYMN-UHFFFAOYSA-N 0.000 claims 3
- WBYVQJVFAXGBRV-UHFFFAOYSA-N 3-[[4-[1-[3,5-dimethyl-4-(4-propan-2-ylphenyl)phenoxy]-5,5,5-trifluoropentyl]benzoyl]amino]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1C(C(=C1)C)=C(C)C=C1OC(CCCC(F)(F)F)C1=CC=C(C(=O)NCCC(O)=O)C=C1 WBYVQJVFAXGBRV-UHFFFAOYSA-N 0.000 claims 3
- FOIKYCSBGDTHPW-UHFFFAOYSA-N 3-[[4-[1-[3,5-dimethyl-4-[4-(trifluoromethoxy)phenyl]phenoxy]-3,3-dimethylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C(C)=C(C=2C=CC(OC(F)(F)F)=CC=2)C(C)=CC=1OC(CC(C)(C)C)C1=CC=C(C(=O)NCCC(O)=O)C=C1 FOIKYCSBGDTHPW-UHFFFAOYSA-N 0.000 claims 3
- DOBLBOPYLZRYFE-UHFFFAOYSA-N 3-[[4-[1-[3,5-dimethyl-4-[4-(trifluoromethoxy)phenyl]phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1C)=CC(C)=C1C1=CC=C(OC(F)(F)F)C=C1 DOBLBOPYLZRYFE-UHFFFAOYSA-N 0.000 claims 3
- IKVWDUGWPRTGQC-UHFFFAOYSA-N 3-[[4-[1-[3,5-dimethyl-4-[4-(trifluoromethyl)phenyl]phenoxy]-2-methylpropyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(C(C)C)OC(C=C1C)=CC(C)=C1C1=CC=C(C(F)(F)F)C=C1 IKVWDUGWPRTGQC-UHFFFAOYSA-N 0.000 claims 3
- ACGOWLJCWDDVLQ-UHFFFAOYSA-N 3-[[4-[1-[3,5-dimethyl-4-[4-(trifluoromethyl)phenyl]phenoxy]-3,3-dimethylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C(C)=C(C=2C=CC(=CC=2)C(F)(F)F)C(C)=CC=1OC(CC(C)(C)C)C1=CC=C(C(=O)NCCC(O)=O)C=C1 ACGOWLJCWDDVLQ-UHFFFAOYSA-N 0.000 claims 3
- DRSKYEQDXXYBKN-UHFFFAOYSA-N 3-[[4-[1-[3,5-dimethyl-4-[4-(trifluoromethyl)phenyl]phenoxy]-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=C1C)=CC(C)=C1C1=CC=C(C(F)(F)F)C=C1 DRSKYEQDXXYBKN-UHFFFAOYSA-N 0.000 claims 3
- CELZMFIKHZGKKC-UHFFFAOYSA-N 3-[[4-[1-[3,5-dimethyl-4-[4-(trifluoromethyl)phenyl]phenoxy]-4,4,4-trifluorobutyl]benzoyl]amino]propanoic acid Chemical compound C=1C(C)=C(C=2C=CC(=CC=2)C(F)(F)F)C(C)=CC=1OC(CCC(F)(F)F)C1=CC=C(C(=O)NCCC(O)=O)C=C1 CELZMFIKHZGKKC-UHFFFAOYSA-N 0.000 claims 3
- ONAYOXKBQUQBSY-UHFFFAOYSA-N 3-[[4-[1-[3,5-dimethyl-4-[4-(trifluoromethyl)phenyl]phenoxy]-5,5,5-trifluoropentyl]benzoyl]amino]propanoic acid Chemical compound C=1C(C)=C(C=2C=CC(=CC=2)C(F)(F)F)C(C)=CC=1OC(CCCC(F)(F)F)C1=CC=C(C(=O)NCCC(O)=O)C=C1 ONAYOXKBQUQBSY-UHFFFAOYSA-N 0.000 claims 3
- IUAGNFGRIGSELP-UHFFFAOYSA-N 3-[[4-[1-[3,5-dimethyl-4-[4-(trifluoromethyl)phenyl]phenoxy]-5-methylhexyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCC(C)C)OC(C=C1C)=CC(C)=C1C1=CC=C(C(F)(F)F)C=C1 IUAGNFGRIGSELP-UHFFFAOYSA-N 0.000 claims 3
- JQUQVTTYPFUUDO-UHFFFAOYSA-N 3-[[4-[1-[3,5-dimethyl-4-[4-(trifluoromethyl)phenyl]phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1C)=CC(C)=C1C1=CC=C(C(F)(F)F)C=C1 JQUQVTTYPFUUDO-UHFFFAOYSA-N 0.000 claims 3
- OSSOGAYWJZEMMA-UHFFFAOYSA-N 3-[[4-[1-[3,5-dimethyl-4-[4-(trifluoromethyl)phenyl]phenyl]sulfanyl-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)SC(C=C1C)=CC(C)=C1C1=CC=C(C(F)(F)F)C=C1 OSSOGAYWJZEMMA-UHFFFAOYSA-N 0.000 claims 3
- UUYKWCRLLJRYBW-UHFFFAOYSA-N 3-[[4-[1-[3-chloro-4-(4-propan-2-ylphenyl)phenoxy]-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=C1Cl)=CC=C1C1=CC=C(C(C)C)C=C1 UUYKWCRLLJRYBW-UHFFFAOYSA-N 0.000 claims 3
- QESGIFTZFFPZAP-UHFFFAOYSA-N 3-[[4-[1-[3-chloro-4-[4-(trifluoromethyl)phenyl]phenoxy]-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=C1Cl)=CC=C1C1=CC=C(C(F)(F)F)C=C1 QESGIFTZFFPZAP-UHFFFAOYSA-N 0.000 claims 3
- QLXBXPSZLACKEE-UHFFFAOYSA-N 3-[[4-[1-[3-cyano-4-(4-propan-2-ylphenyl)phenoxy]-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=C1C#N)=CC=C1C1=CC=C(C(C)C)C=C1 QLXBXPSZLACKEE-UHFFFAOYSA-N 0.000 claims 3
- GNGZNTXDUXYVPR-UHFFFAOYSA-N 3-[[4-[1-[3-ethyl-4-[4-(trifluoromethyl)phenyl]phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1CC)=CC=C1C1=CC=C(C(F)(F)F)C=C1 GNGZNTXDUXYVPR-UHFFFAOYSA-N 0.000 claims 3
- CIBYLWSSHSAOKM-UHFFFAOYSA-N 3-[[4-[1-[3-methoxy-4-(4-propan-2-ylphenyl)phenoxy]-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C(C)C)C(OC)=CC=1OC(CC(C)C)C1=CC=C(C(=O)NCCC(O)=O)C=C1 CIBYLWSSHSAOKM-UHFFFAOYSA-N 0.000 claims 3
- RWXIIIVHWMSEMC-UHFFFAOYSA-N 3-[[4-[1-[3-methyl-4-(4-propan-2-ylphenyl)phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1C)=CC=C1C1=CC=C(C(C)C)C=C1 RWXIIIVHWMSEMC-UHFFFAOYSA-N 0.000 claims 3
- NQIVCQWYJWFRIW-UHFFFAOYSA-N 3-[[4-[1-[3-methyl-4-[4-(trifluoromethyl)phenyl]phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1C)=CC=C1C1=CC=C(C(F)(F)F)C=C1 NQIVCQWYJWFRIW-UHFFFAOYSA-N 0.000 claims 3
- DKQGAAXKMWPUBH-UHFFFAOYSA-N 3-[[4-[1-[4-(2-phenylpropan-2-yl)phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1)=CC=C1C(C)(C)C1=CC=CC=C1 DKQGAAXKMWPUBH-UHFFFAOYSA-N 0.000 claims 3
- HIJGMXCQYWWMSJ-UHFFFAOYSA-N 3-[[4-[1-[4-(4-chlorophenyl)-3,5-dimethylphenoxy]-4,4-dimethylpentyl]benzoyl]amino]propanoic acid Chemical compound C=1C(C)=C(C=2C=CC(Cl)=CC=2)C(C)=CC=1OC(CCC(C)(C)C)C1=CC=C(C(=O)NCCC(O)=O)C=C1 HIJGMXCQYWWMSJ-UHFFFAOYSA-N 0.000 claims 3
- MXWCPKQOLRUIKE-UHFFFAOYSA-N 3-[[4-[1-[4-(4-ethylphenyl)-3,5-dimethylphenoxy]-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C1=CC(CC)=CC=C1C(C(=C1)C)=C(C)C=C1OC(CC(C)C)C1=CC=C(C(=O)NCCC(O)=O)C=C1 MXWCPKQOLRUIKE-UHFFFAOYSA-N 0.000 claims 3
- DDQPFKRDXSKRFY-UHFFFAOYSA-N 3-[[4-[1-[4-(4-ethylphenyl)phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1)=CC=C1C1=CC=C(CC)C=C1 DDQPFKRDXSKRFY-UHFFFAOYSA-N 0.000 claims 3
- OTWHWDRCEMPYSX-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)-3,5-dimethylphenoxy]-3,3-dimethylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C(C)=C(C=2C=CC(=CC=2)C(C)(C)C)C(C)=CC=1OC(CC(C)(C)C)C1=CC=C(C(=O)NCCC(O)=O)C=C1 OTWHWDRCEMPYSX-UHFFFAOYSA-N 0.000 claims 3
- YXCNSMPUDZMRHG-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)-3,5-dimethylphenoxy]-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=C1C)=CC(C)=C1C1=CC=C(C(C)(C)C)C=C1 YXCNSMPUDZMRHG-UHFFFAOYSA-N 0.000 claims 3
- KSTCJQKMQHKIHW-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)-3,5-dimethylphenoxy]-5,5,5-trifluoropentyl]benzoyl]amino]propanoic acid Chemical compound C=1C(C)=C(C=2C=CC(=CC=2)C(C)(C)C)C(C)=CC=1OC(CCCC(F)(F)F)C1=CC=C(C(=O)NCCC(O)=O)C=C1 KSTCJQKMQHKIHW-UHFFFAOYSA-N 0.000 claims 3
- HWFPEDDQCGOTCV-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)-3,5-dimethylphenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1C)=CC(C)=C1C1=CC=C(C(C)(C)C)C=C1 HWFPEDDQCGOTCV-UHFFFAOYSA-N 0.000 claims 3
- LERSGUCLTVBKFU-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)-3,5-dimethylphenyl]sulfanyl-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)SC(C=C1C)=CC(C)=C1C1=CC=C(C(C)(C)C)C=C1 LERSGUCLTVBKFU-UHFFFAOYSA-N 0.000 claims 3
- MDRIPIUBQOIOAU-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)-3,5-dimethylphenyl]sulfanyl-4,4,4-trifluorobutyl]benzoyl]amino]propanoic acid Chemical compound C=1C(C)=C(C=2C=CC(=CC=2)C(C)(C)C)C(C)=CC=1SC(CCC(F)(F)F)C1=CC=C(C(=O)NCCC(O)=O)C=C1 MDRIPIUBQOIOAU-UHFFFAOYSA-N 0.000 claims 3
- ABJCPKIFFABSJV-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)-3-(trifluoromethyl)phenoxy]-2-methylpropyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(C(C)C)OC(C=C1C(F)(F)F)=CC=C1C1=CC=C(C(C)(C)C)C=C1 ABJCPKIFFABSJV-UHFFFAOYSA-N 0.000 claims 3
- YNLUKPGPKVSPME-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)-3-(trifluoromethyl)phenoxy]-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=C1C(F)(F)F)=CC=C1C1=CC=C(C(C)(C)C)C=C1 YNLUKPGPKVSPME-UHFFFAOYSA-N 0.000 claims 3
- KPQXLEDGTXHZSK-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)-3-(trifluoromethyl)phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1C(F)(F)F)=CC=C1C1=CC=C(C(C)(C)C)C=C1 KPQXLEDGTXHZSK-UHFFFAOYSA-N 0.000 claims 3
- TYTKVKWIGOKBNL-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)-3-(trifluoromethyl)phenoxy]pentyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCC)OC(C=C1C(F)(F)F)=CC=C1C1=CC=C(C(C)(C)C)C=C1 TYTKVKWIGOKBNL-UHFFFAOYSA-N 0.000 claims 3
- CURWQRPSQJEVFG-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)-3-methylphenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1C)=CC=C1C1=CC=C(C(C)(C)C)C=C1 CURWQRPSQJEVFG-UHFFFAOYSA-N 0.000 claims 3
- LCQODXISZIEPIJ-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)phenoxy]-3-methylbutyl]-3-fluorobenzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=C(F)C=1C(CC(C)C)OC(C=C1)=CC=C1C1=CC=C(C(C)(C)C)C=C1 LCQODXISZIEPIJ-UHFFFAOYSA-N 0.000 claims 3
- ZTUNIZPAWRAKFQ-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)phenoxy]-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=C1)=CC=C1C1=CC=C(C(C)(C)C)C=C1 ZTUNIZPAWRAKFQ-UHFFFAOYSA-N 0.000 claims 3
- RGCXBKFOWNYUHZ-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)phenoxy]-4,4,4-trifluorobutyl]benzoyl]amino]propanoic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C(C=C1)=CC=C1OC(CCC(F)(F)F)C1=CC=C(C(=O)NCCC(O)=O)C=C1 RGCXBKFOWNYUHZ-UHFFFAOYSA-N 0.000 claims 3
- GDCYCTGVCQJKPW-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)phenoxy]-5,5,5-trifluoropentyl]benzoyl]amino]propanoic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C(C=C1)=CC=C1OC(CCCC(F)(F)F)C1=CC=C(C(=O)NCCC(O)=O)C=C1 GDCYCTGVCQJKPW-UHFFFAOYSA-N 0.000 claims 3
- AWNGCPZBQKAEIN-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)phenoxy]butyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCC)OC(C=C1)=CC=C1C1=CC=C(C(C)(C)C)C=C1 AWNGCPZBQKAEIN-UHFFFAOYSA-N 0.000 claims 3
- QNYCDPWHSVGLPR-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)phenoxy]heptyl]-3-fluorobenzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=C(F)C=1C(CCCCCC)OC(C=C1)=CC=C1C1=CC=C(C(C)(C)C)C=C1 QNYCDPWHSVGLPR-UHFFFAOYSA-N 0.000 claims 3
- QUZPFKQOPXCRBE-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1)=CC=C1C1=CC=C(C(C)(C)C)C=C1 QUZPFKQOPXCRBE-UHFFFAOYSA-N 0.000 claims 3
- IVFLFFPRMYSUFU-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)phenoxy]hexyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCC)OC(C=C1)=CC=C1C1=CC=C(C(C)(C)C)C=C1 IVFLFFPRMYSUFU-UHFFFAOYSA-N 0.000 claims 3
- IELFAHBBOBEISU-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)phenoxy]pentyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCC)OC(C=C1)=CC=C1C1=CC=C(C(C)(C)C)C=C1 IELFAHBBOBEISU-UHFFFAOYSA-N 0.000 claims 3
- WOJVUYQOVGOLRN-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)phenoxy]propyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC)OC(C=C1)=CC=C1C1=CC=C(C(C)(C)C)C=C1 WOJVUYQOVGOLRN-UHFFFAOYSA-N 0.000 claims 3
- VSDWYNZZCAQBMP-UHFFFAOYSA-N 3-[[4-[1-[4-[4-(trifluoromethyl)phenoxy]phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 VSDWYNZZCAQBMP-UHFFFAOYSA-N 0.000 claims 3
- MJHPKPASKRCFIQ-UHFFFAOYSA-N 3-[[4-[1-[4-[4-(trifluoromethyl)phenyl]phenoxy]butyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCC)OC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 MJHPKPASKRCFIQ-UHFFFAOYSA-N 0.000 claims 3
- CGSXJYZTNRHKGD-UHFFFAOYSA-N 3-[[4-[1-[4-[4-(trifluoromethyl)phenyl]phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 CGSXJYZTNRHKGD-UHFFFAOYSA-N 0.000 claims 3
- FXPOAKWHMWZYBQ-UHFFFAOYSA-N 3-[[4-[1-[4-[4-(trifluoromethyl)phenyl]phenoxy]hexyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCC)OC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 FXPOAKWHMWZYBQ-UHFFFAOYSA-N 0.000 claims 3
- DKLSRPMMGWIUNK-UHFFFAOYSA-N 3-[[4-[1-[4-[4-(trifluoromethyl)phenyl]phenoxy]nonyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCCCC)OC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 DKLSRPMMGWIUNK-UHFFFAOYSA-N 0.000 claims 3
- FDRUCLWJOXILLM-UHFFFAOYSA-N 3-[[4-[1-[4-[4-(trifluoromethyl)phenyl]phenoxy]pentyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCC)OC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 FDRUCLWJOXILLM-UHFFFAOYSA-N 0.000 claims 3
- LWEWOQRMSZEKEG-UHFFFAOYSA-N 3-[[4-[1-[4-[4-(trifluoromethyl)phenyl]phenoxy]propyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC)OC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 LWEWOQRMSZEKEG-UHFFFAOYSA-N 0.000 claims 3
- RPZRSVXFJCWLFU-UHFFFAOYSA-N 3-[[4-[1-[4-[4-(trifluoromethyl)phenyl]phenyl]sulfanylheptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)SC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 RPZRSVXFJCWLFU-UHFFFAOYSA-N 0.000 claims 3
- ZETXYZGLMGUTJH-UHFFFAOYSA-N 3-[[4-[1-[6-(4-tert-butylphenyl)pyridin-3-yl]oxy-4,4,4-trifluorobutyl]benzoyl]amino]propanoic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N=C1)=CC=C1OC(CCC(F)(F)F)C1=CC=C(C(=O)NCCC(O)=O)C=C1 ZETXYZGLMGUTJH-UHFFFAOYSA-N 0.000 claims 3
- XHGOIDVSPHIYNL-UHFFFAOYSA-N 3-[[4-[1-[6-(4-tert-butylphenyl)pyridin-3-yl]oxy-5-methylhexyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCC(C)C)OC(C=N1)=CC=C1C1=CC=C(C(C)(C)C)C=C1 XHGOIDVSPHIYNL-UHFFFAOYSA-N 0.000 claims 3
- WRNIHDZHAXIBEQ-UHFFFAOYSA-N 3-[[4-[1-[6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]oxyheptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=N1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 WRNIHDZHAXIBEQ-UHFFFAOYSA-N 0.000 claims 3
- OBQLWFKMHHRMSV-UHFFFAOYSA-N 3-[[4-[1-[6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]oxypentyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCC)OC(C=N1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 OBQLWFKMHHRMSV-UHFFFAOYSA-N 0.000 claims 3
- SZYNDWGNTAMRBF-UHFFFAOYSA-N 3-[[4-[2-methyl-1-[3-methyl-4-[4-(trifluoromethyl)phenyl]phenoxy]propyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(C(C)C)OC(C=C1C)=CC=C1C1=CC=C(C(F)(F)F)C=C1 SZYNDWGNTAMRBF-UHFFFAOYSA-N 0.000 claims 3
- VLRYCPJEKYSWGO-UHFFFAOYSA-N 3-[[4-[2-methyl-1-[4-[4-(trifluoromethyl)phenyl]phenoxy]propyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(C(C)C)OC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 VLRYCPJEKYSWGO-UHFFFAOYSA-N 0.000 claims 3
- LNOCEPXFUSPVPQ-UHFFFAOYSA-N 3-[[4-[3-methyl-1-[3-methyl-4-(4-propan-2-ylphenyl)phenoxy]butyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=C1C)=CC=C1C1=CC=C(C(C)C)C=C1 LNOCEPXFUSPVPQ-UHFFFAOYSA-N 0.000 claims 3
- CGXMXHJCUOGLIT-UHFFFAOYSA-N 3-[[4-[3-methyl-1-[4-[5-(trifluoromethyl)pyridin-2-yl]phenoxy]butyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=N1 CGXMXHJCUOGLIT-UHFFFAOYSA-N 0.000 claims 3
- ULRCQLQEOGGTKV-UHFFFAOYSA-N 3-[[4-[3-methyl-1-[4-[6-(trifluoromethyl)pyridin-3-yl]phenoxy]butyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)N=C1 ULRCQLQEOGGTKV-UHFFFAOYSA-N 0.000 claims 3
- MLLJABZIDYCYAI-UHFFFAOYSA-N 3-[[4-[3-methyl-1-[5-methyl-6-(4-propan-2-ylphenyl)pyridin-3-yl]oxybutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=C1C)=CN=C1C1=CC=C(C(C)C)C=C1 MLLJABZIDYCYAI-UHFFFAOYSA-N 0.000 claims 3
- KCNFWUROXNHKKB-UHFFFAOYSA-N 3-[[4-[3-methyl-1-[5-methyl-6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]oxybutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=C1C)=CN=C1C1=CC=C(C(F)(F)F)C=C1 KCNFWUROXNHKKB-UHFFFAOYSA-N 0.000 claims 3
- QHYKBQUUDBQJBW-UHFFFAOYSA-N 3-[[4-[4,4,4-trifluoro-1-[4-[4-(trifluoromethyl)phenyl]phenoxy]butyl]benzoyl]amino]propanoic acid Chemical compound C1=CC(C(=O)NCCC(=O)O)=CC=C1C(CCC(F)(F)F)OC1=CC=C(C=2C=CC(=CC=2)C(F)(F)F)C=C1 QHYKBQUUDBQJBW-UHFFFAOYSA-N 0.000 claims 3
- SSDDUKTYNVZKEK-UHFFFAOYSA-N 3-[[4-[4,4,4-trifluoro-1-[6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]oxybutyl]benzoyl]amino]propanoic acid Chemical compound C1=CC(C(=O)NCCC(=O)O)=CC=C1C(CCC(F)(F)F)OC1=CC=C(C=2C=CC(=CC=2)C(F)(F)F)N=C1 SSDDUKTYNVZKEK-UHFFFAOYSA-N 0.000 claims 3
- MHUAHZSMEDSRLE-UHFFFAOYSA-N 3-[[4-[4,4-dimethyl-1-[4-[4-(trifluoromethyl)phenyl]phenoxy]pentyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCC(C)(C)C)OC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 MHUAHZSMEDSRLE-UHFFFAOYSA-N 0.000 claims 3
- BMTRKUBQCQJDTL-UHFFFAOYSA-N 3-[[4-[5,5,5-trifluoro-1-[4-(4-propan-2-ylphenyl)phenoxy]pentyl]benzoyl]amino]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1C(C=C1)=CC=C1OC(CCCC(F)(F)F)C1=CC=C(C(=O)NCCC(O)=O)C=C1 BMTRKUBQCQJDTL-UHFFFAOYSA-N 0.000 claims 3
- KKEHRXCIOKTICI-UHFFFAOYSA-N 3-[[4-[5,5,5-trifluoro-1-[4-[4-(trifluoromethyl)phenyl]phenoxy]pentyl]benzoyl]amino]propanoic acid Chemical compound C1=CC(C(=O)NCCC(=O)O)=CC=C1C(CCCC(F)(F)F)OC1=CC=C(C=2C=CC(=CC=2)C(F)(F)F)C=C1 KKEHRXCIOKTICI-UHFFFAOYSA-N 0.000 claims 3
- PDOXOYNDORRESQ-UHFFFAOYSA-N 3-[[4-[5,5,5-trifluoro-1-[5-methyl-6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]oxypentyl]benzoyl]amino]propanoic acid Chemical compound C=1N=C(C=2C=CC(=CC=2)C(F)(F)F)C(C)=CC=1OC(CCCC(F)(F)F)C1=CC=C(C(=O)NCCC(O)=O)C=C1 PDOXOYNDORRESQ-UHFFFAOYSA-N 0.000 claims 3
- PLWSFHKKEUETGX-UHFFFAOYSA-N 3-[[4-[5-methyl-1-[4-[4-(trifluoromethyl)phenyl]phenoxy]hexyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCC(C)C)OC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 PLWSFHKKEUETGX-UHFFFAOYSA-N 0.000 claims 3
- FCJLQPPOORVTIP-UHFFFAOYSA-N 3-[[4-[cyclohexyl-[4-[4-(trifluoromethyl)phenyl]phenoxy]methyl]benzoyl]amino]propanoic acid Chemical compound C1=CC(C(=O)NCCC(=O)O)=CC=C1C(C1CCCCC1)OC1=CC=C(C=2C=CC(=CC=2)C(F)(F)F)C=C1 FCJLQPPOORVTIP-UHFFFAOYSA-N 0.000 claims 3
- VLSLVIDWWHRHOT-UHFFFAOYSA-N 3-[[4-[cyclopropyl-[4-[4-(trifluoromethyl)phenyl]phenoxy]methyl]benzoyl]amino]propanoic acid Chemical compound C1=CC(C(=O)NCCC(=O)O)=CC=C1C(C1CC1)OC1=CC=C(C=2C=CC(=CC=2)C(F)(F)F)C=C1 VLSLVIDWWHRHOT-UHFFFAOYSA-N 0.000 claims 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- QNVKUZCYKVLYFG-UHFFFAOYSA-N 3-[[4-[1-(4-bromo-3,5-dimethylphenyl)sulfanyl-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)SC1=CC(C)=C(Br)C(C)=C1 QNVKUZCYKVLYFG-UHFFFAOYSA-N 0.000 claims 2
- TZMBAAOTXXIBMA-UHFFFAOYSA-N 3-[[4-[1-(4-bromo-3,5-dimethylphenyl)sulfanyl-4,4,4-trifluorobutyl]benzoyl]amino]propanoic acid Chemical compound CC1=C(Br)C(C)=CC(SC(CCC(F)(F)F)C=2C=CC(=CC=2)C(=O)NCCC(O)=O)=C1 TZMBAAOTXXIBMA-UHFFFAOYSA-N 0.000 claims 2
- SYQCOSNUILKHCI-UHFFFAOYSA-N 3-[[4-[1-(4-pentylphenoxy)heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC1=CC=C(CCCCC)C=C1 SYQCOSNUILKHCI-UHFFFAOYSA-N 0.000 claims 2
- PYALZTPVPPLSBC-UHFFFAOYSA-N 3-[[4-[1-[3,5-dimethyl-4-(4-propan-2-ylphenyl)phenoxy]-3,3-dimethylbutyl]benzoyl]amino]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1C(C(=C1)C)=C(C)C=C1OC(CC(C)(C)C)C1=CC=C(C(=O)NCCC(O)=O)C=C1 PYALZTPVPPLSBC-UHFFFAOYSA-N 0.000 claims 2
- UQQRJSRQSUIPNF-UHFFFAOYSA-N 3-[[4-[1-[3,5-dimethyl-4-[4-(trifluoromethyl)phenyl]phenoxy]-3,3-dimethylbutyl]benzoyl]amino]-2-hydroxypropanoic acid Chemical compound C=1C(C)=C(C=2C=CC(=CC=2)C(F)(F)F)C(C)=CC=1OC(CC(C)(C)C)C1=CC=C(C(=O)NCC(O)C(O)=O)C=C1 UQQRJSRQSUIPNF-UHFFFAOYSA-N 0.000 claims 2
- ZEISKDBZKMNDHL-UHFFFAOYSA-N 3-[[4-[1-[3,5-dimethyl-4-[4-(trifluoromethyl)phenyl]phenoxy]-3-methylbutyl]benzoyl]amino]-2-hydroxypropanoic acid Chemical compound C=1C=C(C(=O)NCC(O)C(O)=O)C=CC=1C(CC(C)C)OC(C=C1C)=CC(C)=C1C1=CC=C(C(F)(F)F)C=C1 ZEISKDBZKMNDHL-UHFFFAOYSA-N 0.000 claims 2
- TYLGMIXJGSNRMC-UHFFFAOYSA-N 3-[[4-[1-[3,5-dimethyl-4-[4-(trifluoromethyl)phenyl]phenyl]sulfanyl-5,5,5-trifluoropentyl]benzoyl]amino]propanoic acid Chemical compound C=1C(C)=C(C=2C=CC(=CC=2)C(F)(F)F)C(C)=CC=1SC(CCCC(F)(F)F)C1=CC=C(C(=O)NCCC(O)=O)C=C1 TYLGMIXJGSNRMC-UHFFFAOYSA-N 0.000 claims 2
- IPYRFSITBNNVLJ-UHFFFAOYSA-N 3-[[4-[1-[3-chloro-4-(2,4-dichlorophenyl)phenoxy]-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=C1Cl)=CC=C1C1=CC=C(Cl)C=C1Cl IPYRFSITBNNVLJ-UHFFFAOYSA-N 0.000 claims 2
- POGVUXMKUUSCKD-UHFFFAOYSA-N 3-[[4-[1-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC1=CC=C(C(C)(C)CC(C)(C)C)C=C1 POGVUXMKUUSCKD-UHFFFAOYSA-N 0.000 claims 2
- PAOZBRUYJCCRNA-UHFFFAOYSA-N 3-[[4-[1-[4-(3,5-dichlorophenyl)phenoxy]butyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCC)OC(C=C1)=CC=C1C1=CC(Cl)=CC(Cl)=C1 PAOZBRUYJCCRNA-UHFFFAOYSA-N 0.000 claims 2
- BLSPWGNEOOPLDC-UHFFFAOYSA-N 3-[[4-[1-[4-(4-ethylphenyl)-3-methylphenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1C)=CC=C1C1=CC=C(CC)C=C1 BLSPWGNEOOPLDC-UHFFFAOYSA-N 0.000 claims 2
- SVBQFTLVCNHVTP-UHFFFAOYSA-N 3-[[4-[1-[4-(4-fluorophenyl)-3-methylphenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1C)=CC=C1C1=CC=C(F)C=C1 SVBQFTLVCNHVTP-UHFFFAOYSA-N 0.000 claims 2
- GNGNGQFAWZUWOW-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)-3-methylphenoxy]-3-methylbutyl]-3-fluorobenzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=C(F)C=1C(CC(C)C)OC(C=C1C)=CC=C1C1=CC=C(C(C)(C)C)C=C1 GNGNGQFAWZUWOW-UHFFFAOYSA-N 0.000 claims 2
- MYZUFCORAKGKIG-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)phenoxy]-2-methylpropyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(C(C)C)OC(C=C1)=CC=C1C1=CC=C(C(C)(C)C)C=C1 MYZUFCORAKGKIG-UHFFFAOYSA-N 0.000 claims 2
- WWBALOFZYQSVEB-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)phenoxy]-3-methylbutyl]benzoyl]amino]-2-hydroxypropanoic acid Chemical compound C=1C=C(C(=O)NCC(O)C(O)=O)C=CC=1C(CC(C)C)OC(C=C1)=CC=C1C1=CC=C(C(C)(C)C)C=C1 WWBALOFZYQSVEB-UHFFFAOYSA-N 0.000 claims 2
- UHAYYLBMJJBVBJ-UHFFFAOYSA-N 3-[[4-[1-[4-[3,5-bis(trifluoromethyl)phenyl]phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1)=CC=C1C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 UHAYYLBMJJBVBJ-UHFFFAOYSA-N 0.000 claims 2
- CQEKRBPMWCGVSX-UHFFFAOYSA-N 3-[[4-[1-[4-[4-(2-fluoropropan-2-yl)phenyl]phenyl]sulfanyl-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)SC(C=C1)=CC=C1C1=CC=C(C(C)(C)F)C=C1 CQEKRBPMWCGVSX-UHFFFAOYSA-N 0.000 claims 2
- ZKPDHCPHRBCINE-UHFFFAOYSA-N 3-[[4-[1-[4-[4-(trifluoromethoxy)phenyl]phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 ZKPDHCPHRBCINE-UHFFFAOYSA-N 0.000 claims 2
- SSZANYZSCVMDPS-UHFFFAOYSA-N 3-[[4-[1-[6-(4-tert-butylphenyl)pyridin-3-yl]oxy-4,4-dimethylpentyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCC(C)(C)C)OC(C=N1)=CC=C1C1=CC=C(C(C)(C)C)C=C1 SSZANYZSCVMDPS-UHFFFAOYSA-N 0.000 claims 2
- XGZTYLPEIFJNOF-UHFFFAOYSA-N 3-[[4-[1-[6-(4-tert-butylphenyl)pyridin-3-yl]oxy-5,5,5-trifluoropentyl]benzoyl]amino]propanoic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N=C1)=CC=C1OC(CCCC(F)(F)F)C1=CC=C(C(=O)NCCC(O)=O)C=C1 XGZTYLPEIFJNOF-UHFFFAOYSA-N 0.000 claims 2
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- DZAPAPSYNXKNBU-UHFFFAOYSA-N 3-[[4-[2-methyl-1-[3-methyl-4-[4-(trifluoromethoxy)phenyl]phenoxy]propyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(C(C)C)OC(C=C1C)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 DZAPAPSYNXKNBU-UHFFFAOYSA-N 0.000 claims 2
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- WOURGEDULKUVQF-UHFFFAOYSA-N 3-[[4-[[4-(4-tert-butylphenyl)-3,5-dimethylphenoxy]methyl]benzoyl]amino]propanoic acid Chemical compound C=1C(C)=C(C=2C=CC(=CC=2)C(C)(C)C)C(C)=CC=1OCC1=CC=C(C(=O)NCCC(O)=O)C=C1 WOURGEDULKUVQF-UHFFFAOYSA-N 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- WWBALOFZYQSVEB-QXPUDEPPSA-N (2r)-3-[[4-[1-[4-(4-tert-butylphenyl)phenoxy]-3-methylbutyl]benzoyl]amino]-2-hydroxypropanoic acid Chemical compound C=1C=C(C(=O)NC[C@@H](O)C(O)=O)C=CC=1C(CC(C)C)OC(C=C1)=CC=C1C1=CC=C(C(C)(C)C)C=C1 WWBALOFZYQSVEB-QXPUDEPPSA-N 0.000 claims 1
- WWBALOFZYQSVEB-MBMZGMDYSA-N (2s)-3-[[4-[1-[4-(4-tert-butylphenyl)phenoxy]-3-methylbutyl]benzoyl]amino]-2-hydroxypropanoic acid Chemical compound C=1C=C(C(=O)NC[C@H](O)C(O)=O)C=CC=1C(CC(C)C)OC(C=C1)=CC=C1C1=CC=C(C(C)(C)C)C=C1 WWBALOFZYQSVEB-MBMZGMDYSA-N 0.000 claims 1
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- KDLFARVPZQGALH-UHFFFAOYSA-N 3-[[4-[1-(3,5-dimethylphenoxy)-5,5,5-trifluoropentyl]benzoyl]amino]propanoic acid Chemical compound CC1=CC(C)=CC(OC(CCCC(F)(F)F)C=2C=CC(=CC=2)C(=O)NCCC(O)=O)=C1 KDLFARVPZQGALH-UHFFFAOYSA-N 0.000 claims 1
- OVFHXNHVPNOYFD-UHFFFAOYSA-N 3-[[4-[1-(3-chloro-4-methylphenoxy)-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC1=CC=C(C)C(Cl)=C1 OVFHXNHVPNOYFD-UHFFFAOYSA-N 0.000 claims 1
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- MSUJUQBALMJDFI-UHFFFAOYSA-N 3-[[4-[1-(4-bromo-3,5-dimethylphenyl)sulfanyl-5,5,5-trifluoropentyl]benzoyl]amino]propanoic acid Chemical compound CC1=C(Br)C(C)=CC(SC(CCCC(F)(F)F)C=2C=CC(=CC=2)C(=O)NCCC(O)=O)=C1 MSUJUQBALMJDFI-UHFFFAOYSA-N 0.000 claims 1
- GBYRAAGJBBHMRA-UHFFFAOYSA-N 3-[[4-[1-(4-bromophenoxy)-5,5,5-trifluoropentyl]benzoyl]amino]propanoic acid Chemical compound C1=CC(C(=O)NCCC(=O)O)=CC=C1C(CCCC(F)(F)F)OC1=CC=C(Br)C=C1 GBYRAAGJBBHMRA-UHFFFAOYSA-N 0.000 claims 1
- AFUCYKHHOFWDTQ-UHFFFAOYSA-N 3-[[4-[1-(4-cyclohexylphenoxy)hexyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCC)OC(C=C1)=CC=C1C1CCCCC1 AFUCYKHHOFWDTQ-UHFFFAOYSA-N 0.000 claims 1
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- MGVLXIBGTVHBLI-UHFFFAOYSA-N 3-[[4-[1-(4-hydroxyphenoxy)heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC1=CC=C(O)C=C1 MGVLXIBGTVHBLI-UHFFFAOYSA-N 0.000 claims 1
- LYMSWYYRHDBEDT-UHFFFAOYSA-N 3-[[4-[1-(4-pentoxyphenoxy)heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC1=CC=C(OCCCCC)C=C1 LYMSWYYRHDBEDT-UHFFFAOYSA-N 0.000 claims 1
- FSDIXLPRCIYLHG-UHFFFAOYSA-N 3-[[4-[1-(6-chloropyridin-3-yl)oxy-4,4,4-trifluorobutyl]benzoyl]amino]propanoic acid Chemical compound C1=CC(C(=O)NCCC(=O)O)=CC=C1C(CCC(F)(F)F)OC1=CC=C(Cl)N=C1 FSDIXLPRCIYLHG-UHFFFAOYSA-N 0.000 claims 1
- OGCIQWIOSUXCET-UHFFFAOYSA-N 3-[[4-[1-(6-chloropyridin-3-yl)oxy-5-methylhexyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCC(C)C)OC1=CC=C(Cl)N=C1 OGCIQWIOSUXCET-UHFFFAOYSA-N 0.000 claims 1
- YQNDZZHMCSBCMW-UHFFFAOYSA-N 3-[[4-[1-[2,6-dimethyl-4-[4-(trifluoromethyl)phenyl]phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C(=C1)C)=C(C)C=C1C1=CC=C(C(F)(F)F)C=C1 YQNDZZHMCSBCMW-UHFFFAOYSA-N 0.000 claims 1
- YHAQSWNDFRLZJZ-UHFFFAOYSA-N 3-[[4-[1-[3,5-difluoro-4-(4-propan-2-ylphenyl)phenoxy]-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=C1F)=CC(F)=C1C1=CC=C(C(C)C)C=C1 YHAQSWNDFRLZJZ-UHFFFAOYSA-N 0.000 claims 1
- CZDHVNSLRYMWLO-UHFFFAOYSA-N 3-[[4-[1-[3,5-difluoro-4-[4-(trifluoromethyl)phenyl]phenoxy]-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=C1F)=CC(F)=C1C1=CC=C(C(F)(F)F)C=C1 CZDHVNSLRYMWLO-UHFFFAOYSA-N 0.000 claims 1
- UFJBQCFCCCNZHU-UHFFFAOYSA-N 3-[[4-[1-[3,5-dimethyl-4-(4-propan-2-ylphenyl)phenoxy]-3,3-dimethylbutyl]benzoyl]amino]-2-hydroxypropanoic acid Chemical compound C1=CC(C(C)C)=CC=C1C(C(=C1)C)=C(C)C=C1OC(CC(C)(C)C)C1=CC=C(C(=O)NCC(O)C(O)=O)C=C1 UFJBQCFCCCNZHU-UHFFFAOYSA-N 0.000 claims 1
- AKOSUTGNWSCMRH-UHFFFAOYSA-N 3-[[4-[1-[3,5-dimethyl-4-(4-propan-2-ylphenyl)phenoxy]-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=C1C)=CC(C)=C1C1=CC=C(C(C)C)C=C1 AKOSUTGNWSCMRH-UHFFFAOYSA-N 0.000 claims 1
- VMVYXTHWQQUOPC-UHFFFAOYSA-N 3-[[4-[1-[3,5-dimethyl-4-(4-propan-2-ylphenyl)phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1C)=CC(C)=C1C1=CC=C(C(C)C)C=C1 VMVYXTHWQQUOPC-UHFFFAOYSA-N 0.000 claims 1
- IZXFUNIKQAOYQG-UHFFFAOYSA-N 3-[[4-[1-[3,5-dimethyl-4-[4-(trifluoromethoxy)phenyl]phenoxy]-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=C1C)=CC(C)=C1C1=CC=C(OC(F)(F)F)C=C1 IZXFUNIKQAOYQG-UHFFFAOYSA-N 0.000 claims 1
- PQJIGAAJZBRKRT-UHFFFAOYSA-N 3-[[4-[1-[3,5-dimethyl-4-[4-(trifluoromethyl)phenyl]phenoxy]ethyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(C)OC(C=C1C)=CC(C)=C1C1=CC=C(C(F)(F)F)C=C1 PQJIGAAJZBRKRT-UHFFFAOYSA-N 0.000 claims 1
- MIDGESQDAOXHOT-UHFFFAOYSA-N 3-[[4-[1-[3,5-dimethyl-4-[4-(trifluoromethyl)phenyl]phenyl]sulfanyl-4,4,4-trifluorobutyl]benzoyl]amino]propanoic acid Chemical compound C=1C(C)=C(C=2C=CC(=CC=2)C(F)(F)F)C(C)=CC=1SC(CCC(F)(F)F)C1=CC=C(C(=O)NCCC(O)=O)C=C1 MIDGESQDAOXHOT-UHFFFAOYSA-N 0.000 claims 1
- MXYSKYLHXBGDDM-UHFFFAOYSA-N 3-[[4-[1-[3-(1,3-dioxan-2-yl)-4-(4-propan-2-ylphenyl)phenoxy]-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=C1C2OCCCO2)=CC=C1C1=CC=C(C(C)C)C=C1 MXYSKYLHXBGDDM-UHFFFAOYSA-N 0.000 claims 1
- NFODFMRQQSTPRP-UHFFFAOYSA-N 3-[[4-[1-[3-(4-tert-butylphenyl)-4-methylphenoxy]-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=1)=CC=C(C)C=1C1=CC=C(C(C)(C)C)C=C1 NFODFMRQQSTPRP-UHFFFAOYSA-N 0.000 claims 1
- FSXSAMJCILXVNK-UHFFFAOYSA-N 3-[[4-[1-[3-(4-tert-butylphenyl)phenoxy]-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=1)=CC=CC=1C1=CC=C(C(C)(C)C)C=C1 FSXSAMJCILXVNK-UHFFFAOYSA-N 0.000 claims 1
- ZLYLTQQBXFIPTR-UHFFFAOYSA-N 3-[[4-[1-[3-(hydroxymethyl)-4-(4-propan-2-ylphenyl)phenoxy]-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=C1CO)=CC=C1C1=CC=C(C(C)C)C=C1 ZLYLTQQBXFIPTR-UHFFFAOYSA-N 0.000 claims 1
- FVHSFLKLLBIJOO-UHFFFAOYSA-N 3-[[4-[1-[3-chloro-4-[4-(trifluoromethyl)phenyl]phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1Cl)=CC=C1C1=CC=C(C(F)(F)F)C=C1 FVHSFLKLLBIJOO-UHFFFAOYSA-N 0.000 claims 1
- HBGSXAIOXKRWPL-UHFFFAOYSA-N 3-[[4-[1-[3-formyl-4-(4-propan-2-ylphenyl)phenoxy]-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=C1C=O)=CC=C1C1=CC=C(C(C)C)C=C1 HBGSXAIOXKRWPL-UHFFFAOYSA-N 0.000 claims 1
- MTBKDJNRJHHVPI-UHFFFAOYSA-N 3-[[4-[1-[3-hydroxy-4-(4-propan-2-ylphenyl)phenoxy]-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=C1O)=CC=C1C1=CC=C(C(C)C)C=C1 MTBKDJNRJHHVPI-UHFFFAOYSA-N 0.000 claims 1
- IWDRHEYABDPRBE-UHFFFAOYSA-N 3-[[4-[1-[3-methyl-4-[4-(trifluoromethoxy)phenyl]phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1C)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 IWDRHEYABDPRBE-UHFFFAOYSA-N 0.000 claims 1
- WTISSISDZLSPAV-UHFFFAOYSA-N 3-[[4-[1-[4-(2,3,4-trifluorophenyl)phenoxy]butyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCC)OC(C=C1)=CC=C1C1=CC=C(F)C(F)=C1F WTISSISDZLSPAV-UHFFFAOYSA-N 0.000 claims 1
- RBEXAEJFLZBHCM-UHFFFAOYSA-N 3-[[4-[1-[4-(2,3-dimethylphenyl)phenyl]sulfanylheptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)SC(C=C1)=CC=C1C1=CC=CC(C)=C1C RBEXAEJFLZBHCM-UHFFFAOYSA-N 0.000 claims 1
- JJRRVRMZEPVOOO-UHFFFAOYSA-N 3-[[4-[1-[4-(2,4,6-trimethylphenyl)phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1)=CC=C1C1=C(C)C=C(C)C=C1C JJRRVRMZEPVOOO-UHFFFAOYSA-N 0.000 claims 1
- LTQIIHTUZFNRDV-UHFFFAOYSA-N 3-[[4-[1-[4-(2,4-dimethoxyphenyl)phenoxy]butyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCC)OC(C=C1)=CC=C1C1=CC=C(OC)C=C1OC LTQIIHTUZFNRDV-UHFFFAOYSA-N 0.000 claims 1
- GLQSHAZYLJSUQU-UHFFFAOYSA-N 3-[[4-[1-[4-(2,6-dimethylphenyl)phenyl]sulfanylheptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)SC(C=C1)=CC=C1C1=C(C)C=CC=C1C GLQSHAZYLJSUQU-UHFFFAOYSA-N 0.000 claims 1
- GQSLKSSTHUALIB-UHFFFAOYSA-N 3-[[4-[1-[4-(3,4-dimethylphenyl)phenyl]sulfanyl-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)SC(C=C1)=CC=C1C1=CC=C(C)C(C)=C1 GQSLKSSTHUALIB-UHFFFAOYSA-N 0.000 claims 1
- HUDOVIFINRSGKH-UHFFFAOYSA-N 3-[[4-[1-[4-(3,4-dimethylphenyl)phenyl]sulfanylheptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)SC(C=C1)=CC=C1C1=CC=C(C)C(C)=C1 HUDOVIFINRSGKH-UHFFFAOYSA-N 0.000 claims 1
- HVRWSODVFYFCEO-UHFFFAOYSA-N 3-[[4-[1-[4-(3-acetylphenyl)phenyl]sulfanylheptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)SC(C=C1)=CC=C1C1=CC=CC(C(C)=O)=C1 HVRWSODVFYFCEO-UHFFFAOYSA-N 0.000 claims 1
- IVIVGORLNXPDEM-UHFFFAOYSA-N 3-[[4-[1-[4-(3-propan-2-ylphenyl)phenyl]sulfanylheptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)SC(C=C1)=CC=C1C1=CC=CC(C(C)C)=C1 IVIVGORLNXPDEM-UHFFFAOYSA-N 0.000 claims 1
- HDZOQCNGBQELOB-UHFFFAOYSA-N 3-[[4-[1-[4-(4-acetylphenyl)-3,5-dimethylphenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1C)=CC(C)=C1C1=CC=C(C(C)=O)C=C1 HDZOQCNGBQELOB-UHFFFAOYSA-N 0.000 claims 1
- UXUGPCFZRIPJHB-UHFFFAOYSA-N 3-[[4-[1-[4-(4-acetylphenyl)-3-methylphenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1C)=CC=C1C1=CC=C(C(C)=O)C=C1 UXUGPCFZRIPJHB-UHFFFAOYSA-N 0.000 claims 1
- VYXZQXBBROCOJY-UHFFFAOYSA-N 3-[[4-[1-[4-(4-acetylphenyl)phenoxy]butyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCC)OC(C=C1)=CC=C1C1=CC=C(C(C)=O)C=C1 VYXZQXBBROCOJY-UHFFFAOYSA-N 0.000 claims 1
- RLSBQTJHAPFEMH-UHFFFAOYSA-N 3-[[4-[1-[4-(4-acetylphenyl)phenyl]sulfanylheptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)SC(C=C1)=CC=C1C1=CC=C(C(C)=O)C=C1 RLSBQTJHAPFEMH-UHFFFAOYSA-N 0.000 claims 1
- WCEFMYWZBITPGX-UHFFFAOYSA-N 3-[[4-[1-[4-(4-chlorophenyl)-2,6-dimethylphenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C(=C1)C)=C(C)C=C1C1=CC=C(Cl)C=C1 WCEFMYWZBITPGX-UHFFFAOYSA-N 0.000 claims 1
- PJMBEKUCFILVFZ-UHFFFAOYSA-N 3-[[4-[1-[4-(4-chlorophenyl)-2-methylphenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C(=C1)C)=CC=C1C1=CC=C(Cl)C=C1 PJMBEKUCFILVFZ-UHFFFAOYSA-N 0.000 claims 1
- INTLHCRDSOODCG-UHFFFAOYSA-N 3-[[4-[1-[4-(4-chlorophenyl)-3,5-dimethylphenoxy]-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=C1C)=CC(C)=C1C1=CC=C(Cl)C=C1 INTLHCRDSOODCG-UHFFFAOYSA-N 0.000 claims 1
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- SNOUPZOYUZQTPX-UHFFFAOYSA-N 3-[[4-[1-[4-(4-cyanophenyl)phenyl]sulfanyl-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)SC(C=C1)=CC=C1C1=CC=C(C#N)C=C1 SNOUPZOYUZQTPX-UHFFFAOYSA-N 0.000 claims 1
- YAOZYTRKIOLLSW-UHFFFAOYSA-N 3-[[4-[1-[4-(4-cyclohexylphenyl)phenyl]sulfanylheptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)SC(C=C1)=CC=C1C(C=C1)=CC=C1C1CCCCC1 YAOZYTRKIOLLSW-UHFFFAOYSA-N 0.000 claims 1
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- NWXMTMFMGKTAAA-UHFFFAOYSA-N 3-[[4-[1-[4-(4-fluoro-2-methylphenyl)phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1)=CC=C1C1=CC=C(F)C=C1C NWXMTMFMGKTAAA-UHFFFAOYSA-N 0.000 claims 1
- PEDVHVQIIZHKJZ-UHFFFAOYSA-N 3-[[4-[1-[4-(4-fluorophenyl)-3,5-dimethylphenoxy]-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=C1C)=CC(C)=C1C1=CC=C(F)C=C1 PEDVHVQIIZHKJZ-UHFFFAOYSA-N 0.000 claims 1
- XHLXLHIMCCBTMZ-UHFFFAOYSA-N 3-[[4-[1-[4-(4-fluorophenyl)phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1)=CC=C1C1=CC=C(F)C=C1 XHLXLHIMCCBTMZ-UHFFFAOYSA-N 0.000 claims 1
- GOKUZEASLNWATR-UHFFFAOYSA-N 3-[[4-[1-[4-(4-methylpentoxy)phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC1=CC=C(OCCCC(C)C)C=C1 GOKUZEASLNWATR-UHFFFAOYSA-N 0.000 claims 1
- KDKZLBJRVQJBPE-UHFFFAOYSA-N 3-[[4-[1-[4-(4-methylsulfonylphenyl)phenyl]sulfanylheptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)SC(C=C1)=CC=C1C1=CC=C(S(C)(=O)=O)C=C1 KDKZLBJRVQJBPE-UHFFFAOYSA-N 0.000 claims 1
- MWVNWODAOABXKL-UHFFFAOYSA-N 3-[[4-[1-[4-(4-pentylphenyl)phenoxy]butyl]benzoyl]amino]propanoic acid Chemical compound C1=CC(CCCCC)=CC=C1C(C=C1)=CC=C1OC(CCC)C1=CC=C(C(=O)NCCC(O)=O)C=C1 MWVNWODAOABXKL-UHFFFAOYSA-N 0.000 claims 1
- RRVIYPUYMQQECZ-UHFFFAOYSA-N 3-[[4-[1-[4-(4-pentylphenyl)phenyl]sulfanylheptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)SC(C=C1)=CC=C1C1=CC=C(CCCCC)C=C1 RRVIYPUYMQQECZ-UHFFFAOYSA-N 0.000 claims 1
- FZLRTMAYVMDJHU-UHFFFAOYSA-N 3-[[4-[1-[4-(4-propan-2-ylphenyl)-3-(trifluoromethyl)phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1C(F)(F)F)=CC=C1C1=CC=C(C(C)C)C=C1 FZLRTMAYVMDJHU-UHFFFAOYSA-N 0.000 claims 1
- BVECIJGLVZNUFA-UHFFFAOYSA-N 3-[[4-[1-[4-(4-propan-2-ylphenyl)phenyl]sulfanylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCC)SC(C=C1)=CC=C1C1=CC=C(C(C)C)C=C1 BVECIJGLVZNUFA-UHFFFAOYSA-N 0.000 claims 1
- LUFLZOXJYOTZMN-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)-3,5-dimethylphenoxy]ethyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(C)OC(C=C1C)=CC(C)=C1C1=CC=C(C(C)(C)C)C=C1 LUFLZOXJYOTZMN-UHFFFAOYSA-N 0.000 claims 1
- RIIOFYLNJOASDG-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)-3,5-dimethylphenyl]sulfanyl-5,5,5-trifluoropentyl]benzoyl]amino]propanoic acid Chemical compound C=1C(C)=C(C=2C=CC(=CC=2)C(C)(C)C)C(C)=CC=1SC(CCCC(F)(F)F)C1=CC=C(C(=O)NCCC(O)=O)C=C1 RIIOFYLNJOASDG-UHFFFAOYSA-N 0.000 claims 1
- SCSFYEZTWGPPNE-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)-3-chlorophenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1Cl)=CC=C1C1=CC=C(C(C)(C)C)C=C1 SCSFYEZTWGPPNE-UHFFFAOYSA-N 0.000 claims 1
- USCYPIVBBRGAMD-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)phenoxy]-4,4-dimethylpentyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCC(C)(C)C)OC(C=C1)=CC=C1C1=CC=C(C(C)(C)C)C=C1 USCYPIVBBRGAMD-UHFFFAOYSA-N 0.000 claims 1
- JKTIMSMYDIUSJQ-UHFFFAOYSA-N 3-[[4-[1-[4-(4-tert-butylphenyl)phenoxy]-5-methylhexyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCC(C)C)OC(C=C1)=CC=C1C1=CC=C(C(C)(C)C)C=C1 JKTIMSMYDIUSJQ-UHFFFAOYSA-N 0.000 claims 1
- STOGGVRPNFBULU-UHFFFAOYSA-N 3-[[4-[1-[4-(6-methoxypyridin-3-yl)phenyl]sulfanyl-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C1=NC(OC)=CC=C1C(C=C1)=CC=C1SC(CC(C)C)C1=CC=C(C(=O)NCCC(O)=O)C=C1 STOGGVRPNFBULU-UHFFFAOYSA-N 0.000 claims 1
- ZCAKTCXRYMXNHM-UHFFFAOYSA-N 3-[[4-[1-[4-[(3,4-dimethylphenyl)methoxy]phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1)=CC=C1OCC1=CC=C(C)C(C)=C1 ZCAKTCXRYMXNHM-UHFFFAOYSA-N 0.000 claims 1
- HDBMACOBKNPOHM-UHFFFAOYSA-N 3-[[4-[1-[4-[(3-chlorophenyl)methoxy]phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1)=CC=C1OCC1=CC=CC(Cl)=C1 HDBMACOBKNPOHM-UHFFFAOYSA-N 0.000 claims 1
- RQNNZARUEYJIKX-UHFFFAOYSA-N 3-[[4-[1-[4-[(4-bromophenyl)methoxy]phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1)=CC=C1OCC1=CC=C(Br)C=C1 RQNNZARUEYJIKX-UHFFFAOYSA-N 0.000 claims 1
- OQRLYBFQMYXQJD-UHFFFAOYSA-N 3-[[4-[1-[4-[(4-chlorophenyl)methoxy]phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1)=CC=C1OCC1=CC=C(Cl)C=C1 OQRLYBFQMYXQJD-UHFFFAOYSA-N 0.000 claims 1
- IVNLBUMFCAOKKZ-UHFFFAOYSA-N 3-[[4-[1-[4-[(4-ethylphenyl)methoxy]phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1)=CC=C1OCC1=CC=C(CC)C=C1 IVNLBUMFCAOKKZ-UHFFFAOYSA-N 0.000 claims 1
- WTUUDOASCWBWJC-UHFFFAOYSA-N 3-[[4-[1-[4-[(4-fluorophenyl)methoxy]phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1)=CC=C1OCC1=CC=C(F)C=C1 WTUUDOASCWBWJC-UHFFFAOYSA-N 0.000 claims 1
- HRNWPMZTZKIFIQ-UHFFFAOYSA-N 3-[[4-[1-[4-[(4-phenylphenyl)methoxy]phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1)=CC=C1OCC(C=C1)=CC=C1C1=CC=CC=C1 HRNWPMZTZKIFIQ-UHFFFAOYSA-N 0.000 claims 1
- GKTIFOPYEVIOFO-UHFFFAOYSA-N 3-[[4-[1-[4-[(4-propan-2-ylphenyl)methoxy]phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1)=CC=C1OCC1=CC=C(C(C)C)C=C1 GKTIFOPYEVIOFO-UHFFFAOYSA-N 0.000 claims 1
- FKRFJCQJOPVQPH-UHFFFAOYSA-N 3-[[4-[1-[4-[(4-tert-butylphenyl)methoxy]phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1)=CC=C1OCC1=CC=C(C(C)(C)C)C=C1 FKRFJCQJOPVQPH-UHFFFAOYSA-N 0.000 claims 1
- HEHYOJBGQKEKCC-UHFFFAOYSA-N 3-[[4-[1-[4-[2,4-bis(trifluoromethyl)phenyl]-3-chlorophenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1Cl)=CC=C1C1=CC=C(C(F)(F)F)C=C1C(F)(F)F HEHYOJBGQKEKCC-UHFFFAOYSA-N 0.000 claims 1
- QQTKQARDQWZQIM-UHFFFAOYSA-N 3-[[4-[1-[4-[3-(trifluoromethyl)phenyl]phenyl]sulfanylheptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)SC(C=C1)=CC=C1C1=CC=CC(C(F)(F)F)=C1 QQTKQARDQWZQIM-UHFFFAOYSA-N 0.000 claims 1
- ADCVFNYILFHTQH-UHFFFAOYSA-N 3-[[4-[1-[4-[4-(2-methylpropyl)phenyl]phenoxy]butyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCC)OC(C=C1)=CC=C1C1=CC=C(CC(C)C)C=C1 ADCVFNYILFHTQH-UHFFFAOYSA-N 0.000 claims 1
- KXQVDGBNLDYZNE-UHFFFAOYSA-N 3-[[4-[1-[4-[4-(trifluoromethoxy)phenyl]phenoxy]hexyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCC)OC(C=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 KXQVDGBNLDYZNE-UHFFFAOYSA-N 0.000 claims 1
- DQLAKVPTMALBQV-UHFFFAOYSA-N 3-[[4-[1-[4-[[3,5-bis(trifluoromethyl)phenyl]methoxy]phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1)=CC=C1OCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 DQLAKVPTMALBQV-UHFFFAOYSA-N 0.000 claims 1
- CVPOALVIVYOGME-UHFFFAOYSA-N 3-[[4-[1-[4-[[4-(trifluoromethyl)phenyl]methoxy]phenoxy]heptyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCCCC)OC(C=C1)=CC=C1OCC1=CC=C(C(F)(F)F)C=C1 CVPOALVIVYOGME-UHFFFAOYSA-N 0.000 claims 1
- MBNZTMWWENMYLS-UHFFFAOYSA-N 3-[[4-[1-[4-bromo-3-(1,3-dioxan-2-yl)phenoxy]-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=1)=CC=C(Br)C=1C1OCCCO1 MBNZTMWWENMYLS-UHFFFAOYSA-N 0.000 claims 1
- HYUARFFZIMRSIR-UHFFFAOYSA-N 3-[[4-[1-[4-chloro-3-(trifluoromethyl)phenoxy]heptyl]benzoyl]amino]-2-hydroxypropanoic acid Chemical compound C=1C=C(C(=O)NCC(O)C(O)=O)C=CC=1C(CCCCCC)OC1=CC=C(Cl)C(C(F)(F)F)=C1 HYUARFFZIMRSIR-UHFFFAOYSA-N 0.000 claims 1
- GCYZPAGJCPRDKP-UHFFFAOYSA-N 3-[[4-[1-[6-(4-tert-butylphenyl)pyridin-3-yl]oxy-3-methylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=N1)=CC=C1C1=CC=C(C(C)(C)C)C=C1 GCYZPAGJCPRDKP-UHFFFAOYSA-N 0.000 claims 1
- AREUABAZAWIIIU-UHFFFAOYSA-N 3-[[4-[1-[6-[4-(2-methylpropyl)phenyl]pyridin-3-yl]oxybutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCC)OC(C=N1)=CC=C1C1=CC=C(CC(C)C)C=C1 AREUABAZAWIIIU-UHFFFAOYSA-N 0.000 claims 1
- FVCJNQVBCUCIFX-UHFFFAOYSA-N 3-[[4-[1-[6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]butoxy]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C=2C=CC(=CC=2)C(F)(F)F)N=CC=1C(CCC)OC1=CC=C(C(=O)NCCC(O)=O)C=C1 FVCJNQVBCUCIFX-UHFFFAOYSA-N 0.000 claims 1
- SSLGXDRBOGQNRR-UHFFFAOYSA-N 3-[[4-[2-methyl-1-[3-methyl-4-(4-propan-2-ylphenyl)phenoxy]propyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(C(C)C)OC(C=C1C)=CC=C1C1=CC=C(C(C)C)C=C1 SSLGXDRBOGQNRR-UHFFFAOYSA-N 0.000 claims 1
- ZWBQWVUPRRRSGF-UHFFFAOYSA-N 3-[[4-[2-methyl-1-[4-[6-(trifluoromethyl)pyridin-3-yl]phenoxy]propyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(C(C)C)OC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)N=C1 ZWBQWVUPRRRSGF-UHFFFAOYSA-N 0.000 claims 1
- QRGYAYCZQLFSFZ-UHFFFAOYSA-N 3-[[4-[3-methyl-1-[3-(4-propan-2-ylphenyl)phenoxy]butyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=1)=CC=CC=1C1=CC=C(C(C)C)C=C1 QRGYAYCZQLFSFZ-UHFFFAOYSA-N 0.000 claims 1
- HAKHWGFXWQIUOJ-UHFFFAOYSA-N 3-[[4-[3-methyl-1-[3-(morpholin-4-ylmethyl)-4-(4-propan-2-ylphenyl)phenoxy]butyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=1)=CC=C(C=2C=CC(=CC=2)C(C)C)C=1CN1CCOCC1 HAKHWGFXWQIUOJ-UHFFFAOYSA-N 0.000 claims 1
- GRDJPRRZSOPVOB-UHFFFAOYSA-N 3-[[4-[3-methyl-1-[3-[4-(trifluoromethoxy)phenyl]phenoxy]butyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=1)=CC=CC=1C1=CC=C(OC(F)(F)F)C=C1 GRDJPRRZSOPVOB-UHFFFAOYSA-N 0.000 claims 1
- NPLBHNZZYSHKIL-UHFFFAOYSA-N 3-[[4-[3-methyl-1-[3-[4-(trifluoromethyl)phenyl]phenoxy]butyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=1)=CC=CC=1C1=CC=C(C(F)(F)F)C=C1 NPLBHNZZYSHKIL-UHFFFAOYSA-N 0.000 claims 1
- PZZSELYPURUIEC-UHFFFAOYSA-N 3-[[4-[3-methyl-1-[4-[4-(2-methylpropyl)phenyl]phenyl]sulfanylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)SC(C=C1)=CC=C1C1=CC=C(CC(C)C)C=C1 PZZSELYPURUIEC-UHFFFAOYSA-N 0.000 claims 1
- HDSYLSRMIZVVKJ-UHFFFAOYSA-N 3-[[4-[3-methyl-1-[4-[4-(trifluoromethoxy)phenyl]phenyl]sulfanylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)SC(C=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 HDSYLSRMIZVVKJ-UHFFFAOYSA-N 0.000 claims 1
- YZQKSXAWPACRMR-UHFFFAOYSA-N 3-[[4-[3-methyl-1-[4-[4-(trifluoromethyl)phenyl]phenyl]sulfanylbutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)SC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 YZQKSXAWPACRMR-UHFFFAOYSA-N 0.000 claims 1
- VIAVYRUYEQMYSU-UHFFFAOYSA-N 3-[[4-[3-methyl-1-[4-methyl-3-[4-(trifluoromethyl)phenyl]phenoxy]butyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=1)=CC=C(C)C=1C1=CC=C(C(F)(F)F)C=C1 VIAVYRUYEQMYSU-UHFFFAOYSA-N 0.000 claims 1
- DUSMKNIBGJHCQA-UHFFFAOYSA-N 3-[[4-[3-methyl-1-[6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]oxybutyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CC(C)C)OC(C=N1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 DUSMKNIBGJHCQA-UHFFFAOYSA-N 0.000 claims 1
- GXEBEZLLOMPJSE-UHFFFAOYSA-N 3-[[4-[4,4,4-trifluoro-1-[5-methyl-6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]oxybutyl]benzoyl]amino]propanoic acid Chemical compound C=1N=C(C=2C=CC(=CC=2)C(F)(F)F)C(C)=CC=1OC(CCC(F)(F)F)C1=CC=C(C(=O)NCCC(O)=O)C=C1 GXEBEZLLOMPJSE-UHFFFAOYSA-N 0.000 claims 1
- QZYOKYQTCDICPH-UHFFFAOYSA-N 3-[[4-[4,4,4-trifluoro-1-[6-(4-propan-2-ylphenyl)pyridin-3-yl]oxybutyl]benzoyl]amino]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1C(N=C1)=CC=C1OC(CCC(F)(F)F)C1=CC=C(C(=O)NCCC(O)=O)C=C1 QZYOKYQTCDICPH-UHFFFAOYSA-N 0.000 claims 1
- BCKRDEAWLBJXHY-UHFFFAOYSA-N 3-[[4-[4,4-dimethyl-1-[5-methyl-6-(4-propan-2-ylphenyl)pyridin-3-yl]oxypentyl]benzoyl]amino]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1C(C(=C1)C)=NC=C1OC(CCC(C)(C)C)C1=CC=C(C(=O)NCCC(O)=O)C=C1 BCKRDEAWLBJXHY-UHFFFAOYSA-N 0.000 claims 1
- JTPNGWNNXBIWSD-UHFFFAOYSA-N 3-[[4-[4,4-dimethyl-1-[5-methyl-6-[4-(trifluoromethoxy)phenyl]pyridin-3-yl]oxypentyl]benzoyl]amino]propanoic acid Chemical compound C=1N=C(C=2C=CC(OC(F)(F)F)=CC=2)C(C)=CC=1OC(CCC(C)(C)C)C1=CC=C(C(=O)NCCC(O)=O)C=C1 JTPNGWNNXBIWSD-UHFFFAOYSA-N 0.000 claims 1
- UVJYJGMJTBKPCD-UHFFFAOYSA-N 3-[[4-[4,4-dimethyl-1-[6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]oxypentyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCC(C)(C)C)OC(C=N1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 UVJYJGMJTBKPCD-UHFFFAOYSA-N 0.000 claims 1
- ONIOCCUQOUWFOB-UHFFFAOYSA-N 3-[[4-[5,5,5-trifluoro-1-(2,3,4,5,6-pentamethylphenoxy)pentyl]benzoyl]amino]propanoic acid Chemical compound CC1=C(C)C(C)=C(C)C(C)=C1OC(CCCC(F)(F)F)C1=CC=C(C(=O)NCCC(O)=O)C=C1 ONIOCCUQOUWFOB-UHFFFAOYSA-N 0.000 claims 1
- VENCGBJGFCLCDM-UHFFFAOYSA-N 3-[[4-[5,5,5-trifluoro-1-[2,4,6-tri(propan-2-yl)phenoxy]pentyl]benzoyl]amino]propanoic acid Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1OC(CCCC(F)(F)F)C1=CC=C(C(=O)NCCC(O)=O)C=C1 VENCGBJGFCLCDM-UHFFFAOYSA-N 0.000 claims 1
- GHMFUGAPLAZDCD-UHFFFAOYSA-N 3-[[4-[5,5,5-trifluoro-1-[4-[3-fluoro-4-(trifluoromethyl)phenyl]phenoxy]pentyl]benzoyl]amino]propanoic acid Chemical compound C1=CC(C(=O)NCCC(=O)O)=CC=C1C(CCCC(F)(F)F)OC1=CC=C(C=2C=C(F)C(=CC=2)C(F)(F)F)C=C1 GHMFUGAPLAZDCD-UHFFFAOYSA-N 0.000 claims 1
- NLPUVYDZFPEQHO-UHFFFAOYSA-N 3-[[4-[5,5,5-trifluoro-1-[6-(4-propan-2-ylphenyl)pyridin-3-yl]oxypentyl]benzoyl]amino]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1C(N=C1)=CC=C1OC(CCCC(F)(F)F)C1=CC=C(C(=O)NCCC(O)=O)C=C1 NLPUVYDZFPEQHO-UHFFFAOYSA-N 0.000 claims 1
- WLMMHIKPPIDITF-UHFFFAOYSA-N 3-[[4-[5,5,5-trifluoro-1-[6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]oxypentyl]benzoyl]amino]propanoic acid Chemical compound C1=CC(C(=O)NCCC(=O)O)=CC=C1C(CCCC(F)(F)F)OC1=CC=C(C=2C=CC(=CC=2)C(F)(F)F)N=C1 WLMMHIKPPIDITF-UHFFFAOYSA-N 0.000 claims 1
- FYBAVDHCIGWHNI-UHFFFAOYSA-N 3-[[4-[5-methyl-1-[6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]oxyhexyl]benzoyl]amino]propanoic acid Chemical compound C=1C=C(C(=O)NCCC(O)=O)C=CC=1C(CCCC(C)C)OC(C=N1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 FYBAVDHCIGWHNI-UHFFFAOYSA-N 0.000 claims 1
- JZBNLXCTSZQOGV-UHFFFAOYSA-N 3-[[4-[[4-(4-tert-butylphenyl)-3,5-dimethylphenoxy]-cyclohexylmethyl]benzoyl]amino]propanoic acid Chemical compound C=1C(C)=C(C=2C=CC(=CC=2)C(C)(C)C)C(C)=CC=1OC(C=1C=CC(=CC=1)C(=O)NCCC(O)=O)C1CCCCC1 JZBNLXCTSZQOGV-UHFFFAOYSA-N 0.000 claims 1
- DGYHJQOAPFGKIL-UHFFFAOYSA-N 3-[[4-[[4-(4-tert-butylphenyl)phenoxy]-cyclohexylmethyl]benzoyl]amino]propanoic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C(C=C1)=CC=C1OC(C=1C=CC(=CC=1)C(=O)NCCC(O)=O)C1CCCCC1 DGYHJQOAPFGKIL-UHFFFAOYSA-N 0.000 claims 1
- YLKKRAUGZCBWOE-UHFFFAOYSA-N 3-[[4-[[6-(4-tert-butylphenyl)pyridin-3-yl]oxy-cyclohexylmethyl]benzoyl]amino]propanoic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N=C1)=CC=C1OC(C=1C=CC(=CC=1)C(=O)NCCC(O)=O)C1CCCCC1 YLKKRAUGZCBWOE-UHFFFAOYSA-N 0.000 claims 1
- OMYNTJCMDVPXLH-UHFFFAOYSA-N 3-[[4-[cyclohexyl-[3,5-dimethyl-4-(4-propan-2-ylphenyl)phenoxy]methyl]benzoyl]amino]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1C(C(=C1)C)=C(C)C=C1OC(C=1C=CC(=CC=1)C(=O)NCCC(O)=O)C1CCCCC1 OMYNTJCMDVPXLH-UHFFFAOYSA-N 0.000 claims 1
- POAVHKPQBMVIAU-UHFFFAOYSA-N 3-[[4-[cyclohexyl-[6-(4-propan-2-ylphenyl)pyridin-3-yl]oxymethyl]benzoyl]amino]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1C(N=C1)=CC=C1OC(C=1C=CC(=CC=1)C(=O)NCCC(O)=O)C1CCCCC1 POAVHKPQBMVIAU-UHFFFAOYSA-N 0.000 claims 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000005336 allyloxy group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- BIZGMTWBKDPTLH-UHFFFAOYSA-N propan-2-yl hypochlorite Chemical compound CC(C)OCl BIZGMTWBKDPTLH-UHFFFAOYSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract 1
- 229940125425 inverse agonist Drugs 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000002469 receptor inverse agonist Substances 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
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- A—HUMAN NECESSITIES
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/54—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/64—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton
- C07C323/65—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton containing sulfur atoms of sulfone or sulfoxide groups bound to the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
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- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
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PCT/US2005/019901 WO2005123668A1 (en) | 2004-06-14 | 2005-06-08 | Glucagon receptor antagonists, preparation and therapeutic uses |
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HRP20100148T1 true HRP20100148T1 (hr) | 2010-04-30 |
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HR20100148T HRP20100148T1 (hr) | 2004-06-14 | 2010-03-15 | Antagonisti glukagonskog receptora, priprema i terapijska primjena |
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EP (2) | EP1758853B1 (el) |
JP (1) | JP5000492B2 (el) |
KR (1) | KR100835496B1 (el) |
CN (1) | CN1968921B (el) |
AT (1) | ATE455756T1 (el) |
AU (2) | AU2005254950B2 (el) |
BR (1) | BRPI0512058A (el) |
CA (1) | CA2569459C (el) |
CY (1) | CY1109787T1 (el) |
DE (1) | DE602005019043D1 (el) |
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EA (1) | EA013003B1 (el) |
EC (1) | ECSP067082A (el) |
ES (1) | ES2337596T3 (el) |
HK (1) | HK1104174A1 (el) |
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SI (1) | SI1758853T1 (el) |
UA (1) | UA86621C2 (el) |
WO (1) | WO2005123668A1 (el) |
ZA (1) | ZA200610298B (el) |
Families Citing this family (24)
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PL1758853T3 (pl) * | 2004-06-14 | 2010-06-30 | Lilly Co Eli | Antagoniści receptora glukagonu, wytwarzanie i zastosowania terapeutyczne |
US7524870B2 (en) * | 2004-12-03 | 2009-04-28 | Hoffmann-La Roche Inc. | Biaryloxymethylarenecarboxylic acids as glycogen synthase activators |
KR20070104409A (ko) * | 2005-02-11 | 2007-10-25 | 일라이 릴리 앤드 캄파니 | 글루카곤 수용체 길항제로서의 치환된 티오펜 유도체, 제법및 치료 용도 |
CA2600159A1 (en) * | 2005-03-21 | 2006-09-28 | Merck & Co., Inc. | Substituted aryl and heteroaryl derivatives, compositions containing such compounds and methods of use |
BRPI0618140A2 (pt) * | 2005-11-22 | 2011-08-16 | Lilly Co Eli | composto ou sal farmaceuticamente aceitável do mesmo, composição farmacêutica, e, uso de um composto ou um sal do mesmo |
WO2007136577A2 (en) | 2006-05-16 | 2007-11-29 | Merck & Co., Inc. | Glucagon receptor antagonist compounds, compositions containing such compounds and methods of use |
KR101538810B1 (ko) | 2007-02-09 | 2015-07-22 | 메타베이시스 테라퓨틱스, 인크. | 글루카곤 수용체의 길항제 |
CA2770298C (en) | 2008-08-13 | 2017-06-20 | Metabasis Therapeutics, Inc. | Glucagon antagonists |
US8809579B2 (en) | 2009-02-13 | 2014-08-19 | Merck Sharp & Dohme Corp. | Glucagon receptor antagonist compounds, compositions containing such compounds and methods of use |
US8039495B2 (en) * | 2009-11-16 | 2011-10-18 | Hoffman-La Roche Inc. | Biphenyl carboxylic acids and bioisosteres as glycogen synthase activators |
MX2013006768A (es) | 2010-12-23 | 2013-07-22 | Pfizer | Moduladores de receptor de glucagon. |
IL227559A (en) | 2011-02-08 | 2016-04-21 | Pfizer | Glucagon receptor modulator |
KR20140023441A (ko) | 2011-07-22 | 2014-02-26 | 화이자 인코포레이티드 | 퀴놀린일 글루카곤 수용체 조절제 |
JP2015505828A (ja) | 2011-12-02 | 2015-02-26 | イーライ リリー アンド カンパニー | 抗グルカゴン抗体およびその使用 |
US20140210770A1 (en) * | 2012-10-04 | 2014-07-31 | Corning Incorporated | Pressure sensing touch systems and methods |
TW201427658A (zh) | 2012-12-10 | 2014-07-16 | Merck Sharp & Dohme | 藉由投予升糖素受體拮抗劑及膽固醇吸收抑制劑治療糖尿病之方法 |
EP3065736B1 (en) | 2013-11-04 | 2018-11-14 | Merck Sharp & Dohme Corp. | Glucagon receptor antagonist compounds, compositions thereof, and methods of use |
JP2017519000A (ja) | 2014-06-12 | 2017-07-13 | リガンド・ファーマシューティカルズ・インコーポレイテッド | グルカゴンアンタゴニスト |
WO2017093167A1 (en) | 2015-12-01 | 2017-06-08 | Basf Se | Pyridine compounds as fungicides |
CN108290839A (zh) | 2015-12-01 | 2018-07-17 | 巴斯夫欧洲公司 | 作为杀真菌剂的吡啶化合物 |
CR20190580A (es) | 2017-05-30 | 2020-02-10 | Basf Se | Compuestos de piridina y pirazina |
WO2019160940A1 (en) | 2018-02-13 | 2019-08-22 | Ligand Pharmaceuticals Incorporated | Glucagon receptor antagonists |
CN111184706B (zh) * | 2020-03-05 | 2020-11-17 | 牡丹江医学院 | 一种防治胆囊炎的活性药物及其用途 |
KR102606541B1 (ko) * | 2021-04-23 | 2023-11-29 | 가천대학교 산학협력단 | 바이페닐설폰아마이드 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 글루카곤 수용체 활성 관련 질환의 예방 또는 치료용 약학적 조성물 |
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US4973731A (en) | 1987-04-23 | 1990-11-27 | Riker Laboratories, Inc. | Di-t-butylphenyl alkyl and benzyl ether nitriles |
GB9420557D0 (en) * | 1994-10-12 | 1994-11-30 | Zeneca Ltd | Aromatic compounds |
JP2003504301A (ja) * | 1998-04-01 | 2003-02-04 | ブリストル−マイヤーズ スクイブ ファーマ カンパニー | インテグリンアンタゴニスト |
ES2250128T3 (es) * | 1999-05-17 | 2006-04-16 | Novo Nordisk A/S | Antagonistas/agonistas inversos de glucagon. |
CN1437581A (zh) * | 2000-06-23 | 2003-08-20 | 诺沃挪第克公司 | 胰高血糖素拮抗剂/反向激动剂 |
US6706744B2 (en) * | 2000-11-17 | 2004-03-16 | Novo Nordisk A/S | Glucagon antagonists/inverse agonists |
EP1463715A1 (en) * | 2001-12-03 | 2004-10-06 | Novo Nordisk A/S | Novel glucagon antagonists |
AU2003233780A1 (en) * | 2002-06-27 | 2004-01-19 | Novo Nordisk A/S | Novel glucagon antagonists/inverse agonists |
AU2003291959A1 (en) | 2002-12-20 | 2004-07-14 | Novo Nordisk A/S | Novel glucagon antagonists |
US20080254182A1 (en) | 2004-04-26 | 2008-10-16 | Laurens Last | Packaged Flowable Ice Product, Such as a Milk Shake |
US7989457B2 (en) * | 2004-05-28 | 2011-08-02 | Eli Lilly And Company | Glucagon receptor antagonists, preparation and therapeutic uses |
PL1758853T3 (pl) * | 2004-06-14 | 2010-06-30 | Lilly Co Eli | Antagoniści receptora glukagonu, wytwarzanie i zastosowania terapeutyczne |
KR20070104409A (ko) * | 2005-02-11 | 2007-10-25 | 일라이 릴리 앤드 캄파니 | 글루카곤 수용체 길항제로서의 치환된 티오펜 유도체, 제법및 치료 용도 |
CA2600159A1 (en) | 2005-03-21 | 2006-09-28 | Merck & Co., Inc. | Substituted aryl and heteroaryl derivatives, compositions containing such compounds and methods of use |
ES2391109T3 (es) * | 2005-11-17 | 2012-11-21 | Eli Lilly And Company | Antagonistas del receptor de glucagón, preparación y usos terapéuticos |
JP5198280B2 (ja) * | 2005-11-17 | 2013-05-15 | イーライ リリー アンド カンパニー | グルカゴン受容体アンタゴニスト、並びにその調製及び治療への使用 |
AU2006341392B2 (en) * | 2005-11-18 | 2012-05-17 | Eli Lilly And Company | Glucagon receptor antagonists, preparation and therapeutic uses |
BRPI0618140A2 (pt) * | 2005-11-22 | 2011-08-16 | Lilly Co Eli | composto ou sal farmaceuticamente aceitável do mesmo, composição farmacêutica, e, uso de um composto ou um sal do mesmo |
CA2629311C (en) * | 2005-11-23 | 2014-05-06 | Eli Lilly And Company | Glucagon receptor antagonists, preparation and therapeutic uses |
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- 2005-06-08 AT AT05757998T patent/ATE455756T1/de active
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