RU2016102313A - Биарильные производные в качестве агонистов gpr120 - Google Patents
Биарильные производные в качестве агонистов gpr120 Download PDFInfo
- Publication number
- RU2016102313A RU2016102313A RU2016102313A RU2016102313A RU2016102313A RU 2016102313 A RU2016102313 A RU 2016102313A RU 2016102313 A RU2016102313 A RU 2016102313A RU 2016102313 A RU2016102313 A RU 2016102313A RU 2016102313 A RU2016102313 A RU 2016102313A
- Authority
- RU
- Russia
- Prior art keywords
- butyric acid
- difluoro
- difluorophenoxy
- acid
- pyridyl
- Prior art date
Links
- 102100040134 Free fatty acid receptor 4 Human genes 0.000 title claims 2
- 101000890672 Homo sapiens Free fatty acid receptor 4 Proteins 0.000 title claims 2
- 239000000556 agonist Substances 0.000 title claims 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 123
- -1 C 1 -C 6 -alkylaryl Chemical group 0.000 claims 29
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 26
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 9
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 7
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 7
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 206010012601 diabetes mellitus Diseases 0.000 claims 4
- 239000003937 drug carrier Substances 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 208000004930 Fatty Liver Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 208000001132 Osteoporosis Diseases 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 230000001476 alcoholic effect Effects 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 208000019423 liver disease Diseases 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 1
- 125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 claims 1
- KMWPUGUAAXTHMI-UHFFFAOYSA-N 4-[2,6-difluoro-4-(2-phenoxypyridin-3-yl)phenoxy]butanoic acid Chemical compound C1=C(F)C(OCCCC(=O)O)=C(F)C=C1C1=CC=CN=C1OC1=CC=CC=C1 KMWPUGUAAXTHMI-UHFFFAOYSA-N 0.000 claims 1
- KLVBRQILWOVSPD-UHFFFAOYSA-N 4-[2,6-difluoro-4-(2-piperidin-1-ylpyridin-3-yl)phenoxy]butanoic acid Chemical compound C1=C(F)C(OCCCC(=O)O)=C(F)C=C1C1=CC=CN=C1N1CCCCC1 KLVBRQILWOVSPD-UHFFFAOYSA-N 0.000 claims 1
- BXXLQGOAKQHBAC-UHFFFAOYSA-N 4-[2,6-difluoro-4-(2-propan-2-yloxypyridin-3-yl)phenoxy]butanoic acid Chemical compound CC(C)OC1=NC=CC=C1C1=CC(F)=C(OCCCC(O)=O)C(F)=C1 BXXLQGOAKQHBAC-UHFFFAOYSA-N 0.000 claims 1
- JMCYEEQKCPWZMR-UHFFFAOYSA-N 4-[2,6-difluoro-4-(2-propan-2-ylsulfanylpyridin-3-yl)phenoxy]butanoic acid Chemical compound CC(C)SC1=NC=CC=C1C1=CC(F)=C(OCCCC(O)=O)C(F)=C1 JMCYEEQKCPWZMR-UHFFFAOYSA-N 0.000 claims 1
- SOFZIAPXSKIEDV-UHFFFAOYSA-N 4-[2,6-difluoro-4-(2-propan-2-ylsulfanylpyridin-4-yl)phenoxy]butanoic acid Chemical compound C1=NC(SC(C)C)=CC(C=2C=C(F)C(OCCCC(O)=O)=C(F)C=2)=C1 SOFZIAPXSKIEDV-UHFFFAOYSA-N 0.000 claims 1
- AERWSLMEUPKZGJ-UHFFFAOYSA-N 4-[2,6-difluoro-4-(2-propoxypyridin-3-yl)phenyl]sulfanylbutanoic acid Chemical compound CCCOC1=NC=CC=C1C1=CC(F)=C(SCCCC(O)=O)C(F)=C1 AERWSLMEUPKZGJ-UHFFFAOYSA-N 0.000 claims 1
- PBLGMTWAKXMYQN-UHFFFAOYSA-N 4-[2,6-difluoro-4-(2-pyrrol-1-ylpyridin-3-yl)phenoxy]butanoic acid Chemical compound C1=C(F)C(OCCCC(=O)O)=C(F)C=C1C1=CC=CN=C1N1C=CC=C1 PBLGMTWAKXMYQN-UHFFFAOYSA-N 0.000 claims 1
- OHWQPOTYNFYYRK-UHFFFAOYSA-N 4-[2,6-difluoro-4-(3-pyrrolidin-1-ylphenyl)phenoxy]butanoic acid Chemical compound C1=C(F)C(OCCCC(=O)O)=C(F)C=C1C1=CC=CC(N2CCCC2)=C1 OHWQPOTYNFYYRK-UHFFFAOYSA-N 0.000 claims 1
- PDBLRYUXTKQEGJ-UHFFFAOYSA-N 4-[2,6-difluoro-4-(6-phenoxypyridin-2-yl)phenoxy]butanoic acid Chemical compound C1=C(F)C(OCCCC(=O)O)=C(F)C=C1C1=CC=CC(OC=2C=CC=CC=2)=N1 PDBLRYUXTKQEGJ-UHFFFAOYSA-N 0.000 claims 1
- WYLABCOHBNVGEO-UHFFFAOYSA-N 4-[2,6-difluoro-4-(6-piperidin-1-ylpyridin-2-yl)phenoxy]butanoic acid Chemical compound C1=C(F)C(OCCCC(=O)O)=C(F)C=C1C1=CC=CC(N2CCCCC2)=N1 WYLABCOHBNVGEO-UHFFFAOYSA-N 0.000 claims 1
- CZSAKXHXKVRTDE-UHFFFAOYSA-N 4-[2,6-difluoro-4-(6-propan-2-yloxypyridin-2-yl)phenoxy]butanoic acid Chemical compound CC(C)OC1=CC=CC(C=2C=C(F)C(OCCCC(O)=O)=C(F)C=2)=N1 CZSAKXHXKVRTDE-UHFFFAOYSA-N 0.000 claims 1
- WIJJZFZCPZQFJS-UHFFFAOYSA-N 4-[2,6-difluoro-4-(6-propan-2-yloxypyridin-2-yl)phenyl]sulfanylbutanoic acid Chemical compound CC(C)OC1=CC=CC(C=2C=C(F)C(SCCCC(O)=O)=C(F)C=2)=N1 WIJJZFZCPZQFJS-UHFFFAOYSA-N 0.000 claims 1
- ACZJQBYYNLEVGN-UHFFFAOYSA-N 4-[2,6-difluoro-4-(6-propan-2-ylsulfanylpyridin-2-yl)phenoxy]butanoic acid Chemical compound CC(C)SC1=CC=CC(C=2C=C(F)C(OCCCC(O)=O)=C(F)C=2)=N1 ACZJQBYYNLEVGN-UHFFFAOYSA-N 0.000 claims 1
- YGZWRCUODFLRAQ-UHFFFAOYSA-N 4-[2,6-difluoro-4-(6-propan-2-ylsulfanylpyridin-2-yl)phenyl]sulfanylbutanoic acid Chemical compound CC(C)SC1=CC=CC(C=2C=C(F)C(SCCCC(O)=O)=C(F)C=2)=N1 YGZWRCUODFLRAQ-UHFFFAOYSA-N 0.000 claims 1
- JXYMUMUAOMQMSE-UHFFFAOYSA-N 4-[2,6-difluoro-4-(6-propoxypyridin-2-yl)phenoxy]butanoic acid Chemical compound CCCOC1=CC=CC(C=2C=C(F)C(OCCCC(O)=O)=C(F)C=2)=N1 JXYMUMUAOMQMSE-UHFFFAOYSA-N 0.000 claims 1
- DVKJIPDJNXCILR-UHFFFAOYSA-N 4-[2,6-difluoro-4-(6-propylsulfanylpyridin-2-yl)phenoxy]butanoic acid Chemical compound CCCSC1=CC=CC(C=2C=C(F)C(OCCCC(O)=O)=C(F)C=2)=N1 DVKJIPDJNXCILR-UHFFFAOYSA-N 0.000 claims 1
- FBOGZGNTJUZQMN-UHFFFAOYSA-N 4-[2,6-difluoro-4-(6-pyrrolidin-1-ylpyridin-2-yl)phenoxy]butanoic acid Chemical compound C1=C(F)C(OCCCC(=O)O)=C(F)C=C1C1=CC=CC(N2CCCC2)=N1 FBOGZGNTJUZQMN-UHFFFAOYSA-N 0.000 claims 1
- RTLNGKFMXIZGPB-UHFFFAOYSA-N 4-[2,6-difluoro-4-[2-(3-methylbutylsulfanyl)pyridin-3-yl]phenoxy]butanoic acid Chemical compound CC(C)CCSC1=NC=CC=C1C1=CC(F)=C(OCCCC(O)=O)C(F)=C1 RTLNGKFMXIZGPB-UHFFFAOYSA-N 0.000 claims 1
- JCOSQDQBDIPRRL-UHFFFAOYSA-N 4-[2,6-difluoro-4-[2-(oxan-4-yloxy)pyridin-3-yl]phenoxy]butanoic acid Chemical compound C1=C(F)C(OCCCC(=O)O)=C(F)C=C1C1=CC=CN=C1OC1CCOCC1 JCOSQDQBDIPRRL-UHFFFAOYSA-N 0.000 claims 1
- AZRHGJZPYNBGQY-UHFFFAOYSA-N 4-[2,6-difluoro-4-[2-(oxolan-3-yloxy)pyridin-3-yl]phenoxy]butanoic acid Chemical compound C1=C(F)C(OCCCC(=O)O)=C(F)C=C1C1=CC=CN=C1OC1COCC1 AZRHGJZPYNBGQY-UHFFFAOYSA-N 0.000 claims 1
- MJIHTXRLLGJVAM-UHFFFAOYSA-N 4-[2,6-difluoro-4-[2-(propan-2-ylamino)phenyl]phenoxy]butanoic acid Chemical compound CC(C)NC1=CC=CC=C1C1=CC(F)=C(OCCCC(O)=O)C(F)=C1 MJIHTXRLLGJVAM-UHFFFAOYSA-N 0.000 claims 1
- CSMDUYWPCYKTJO-UHFFFAOYSA-N 4-[2,6-difluoro-4-[2-(propan-2-ylamino)pyridin-3-yl]phenoxy]butanoic acid Chemical compound CC(C)NC1=NC=CC=C1C1=CC(F)=C(OCCCC(O)=O)C(F)=C1 CSMDUYWPCYKTJO-UHFFFAOYSA-N 0.000 claims 1
- VMTBUEUMVCQQLP-UHFFFAOYSA-N 4-[2,6-difluoro-4-[2-(propylamino)phenyl]phenoxy]butanoic acid Chemical compound CCCNC1=CC=CC=C1C1=CC(F)=C(OCCCC(O)=O)C(F)=C1 VMTBUEUMVCQQLP-UHFFFAOYSA-N 0.000 claims 1
- NOSCEBMDURNFBP-UHFFFAOYSA-N 4-[2,6-difluoro-4-[3-(propan-2-ylamino)phenyl]phenoxy]butanoic acid Chemical compound CC(C)NC1=CC=CC(C=2C=C(F)C(OCCCC(O)=O)=C(F)C=2)=C1 NOSCEBMDURNFBP-UHFFFAOYSA-N 0.000 claims 1
- WAFNLWDUHGNVKF-UHFFFAOYSA-N 4-[2,6-difluoro-4-[6-(2-methylprop-1-enyl)pyridin-2-yl]phenoxy]butanoic acid Chemical compound CC(C)=CC1=CC=CC(C=2C=C(F)C(OCCCC(O)=O)=C(F)C=2)=N1 WAFNLWDUHGNVKF-UHFFFAOYSA-N 0.000 claims 1
- YHAGNJOQFLWTGV-UHFFFAOYSA-N 4-[2-chloro-4-(6-propan-2-ylsulfanylpyridin-2-yl)phenoxy]butanoic acid Chemical compound CC(C)SC1=CC=CC(C=2C=C(Cl)C(OCCCC(O)=O)=CC=2)=N1 YHAGNJOQFLWTGV-UHFFFAOYSA-N 0.000 claims 1
- WYPQOWUULRYVKG-UHFFFAOYSA-N 4-[2-fluoro-4-(2-propan-2-ylsulfanylpyridin-3-yl)phenyl]sulfanylbutanoic acid Chemical compound CC(C)SC1=NC=CC=C1C1=CC=C(SCCCC(O)=O)C(F)=C1 WYPQOWUULRYVKG-UHFFFAOYSA-N 0.000 claims 1
- WCLNOCHKVLKKLU-UHFFFAOYSA-N 4-[2-fluoro-4-(2-pyrrolidin-1-ylpyridin-3-yl)phenyl]sulfanylbutanoic acid Chemical compound C1=C(F)C(SCCCC(=O)O)=CC=C1C1=CC=CN=C1N1CCCC1 WCLNOCHKVLKKLU-UHFFFAOYSA-N 0.000 claims 1
- PVXAGWVYHONRHT-UHFFFAOYSA-N 4-[2-fluoro-4-(6-propan-2-yloxypyridin-2-yl)phenyl]sulfanylbutanoic acid Chemical compound CC(C)OC1=CC=CC(C=2C=C(F)C(SCCCC(O)=O)=CC=2)=N1 PVXAGWVYHONRHT-UHFFFAOYSA-N 0.000 claims 1
- IUMIFTQFMHFVIR-UHFFFAOYSA-N 4-[2-fluoro-4-(6-propan-2-ylsulfanylpyridin-2-yl)phenoxy]butanoic acid Chemical compound CC(C)SC1=CC=CC(C=2C=C(F)C(OCCCC(O)=O)=CC=2)=N1 IUMIFTQFMHFVIR-UHFFFAOYSA-N 0.000 claims 1
- FRGFSMCTULBWMX-UHFFFAOYSA-N 4-[4-(2-cyclobutyloxypyridin-3-yl)-2-fluorophenyl]sulfanylbutanoic acid Chemical compound C1=C(F)C(SCCCC(=O)O)=CC=C1C1=CC=CN=C1OC1CCC1 FRGFSMCTULBWMX-UHFFFAOYSA-N 0.000 claims 1
- MMMBHIOHEYRKLI-UHFFFAOYSA-N 4-[4-(2-cyclobutyloxypyridin-3-yl)phenyl]sulfanylbutanoic acid Chemical compound C1=CC(SCCCC(=O)O)=CC=C1C1=CC=CN=C1OC1CCC1 MMMBHIOHEYRKLI-UHFFFAOYSA-N 0.000 claims 1
- UVYNFKHFRVOFHR-UHFFFAOYSA-N 4-[4-(2-cyclobutylsulfanylpyridin-3-yl)-2,5-difluorophenoxy]butanoic acid Chemical compound C1=C(F)C(OCCCC(=O)O)=CC(F)=C1C1=CC=CN=C1SC1CCC1 UVYNFKHFRVOFHR-UHFFFAOYSA-N 0.000 claims 1
- FSDIHQFPBKXMSF-UHFFFAOYSA-N 4-[4-(2-cyclobutylsulfanylpyridin-3-yl)-2,6-difluorophenoxy]pentanoic acid Chemical compound C1=C(F)C(OC(CCC(O)=O)C)=C(F)C=C1C1=CC=CN=C1SC1CCC1 FSDIHQFPBKXMSF-UHFFFAOYSA-N 0.000 claims 1
- ROGWZXKOVQRUHY-UHFFFAOYSA-N 4-[4-(2-cyclobutylsulfanylpyridin-3-yl)-2,6-difluorophenyl]sulfanylbutanoic acid Chemical compound C1=C(F)C(SCCCC(=O)O)=C(F)C=C1C1=CC=CN=C1SC1CCC1 ROGWZXKOVQRUHY-UHFFFAOYSA-N 0.000 claims 1
- QLPDCAJRIYTJCR-UHFFFAOYSA-N 4-[4-(2-cyclobutylsulfanylpyridin-3-yl)-2,6-dimethylphenoxy]butanoic acid Chemical compound CC1=C(OCCCC(O)=O)C(C)=CC(C=2C(=NC=CC=2)SC2CCC2)=C1 QLPDCAJRIYTJCR-UHFFFAOYSA-N 0.000 claims 1
- REXQXPBBKTVIDR-UHFFFAOYSA-N 4-[4-(2-cyclobutylsulfanylpyridin-3-yl)-2-fluorophenyl]sulfanylbutanoic acid Chemical compound C1=C(F)C(SCCCC(=O)O)=CC=C1C1=CC=CN=C1SC1CCC1 REXQXPBBKTVIDR-UHFFFAOYSA-N 0.000 claims 1
- MJVJUFOAXBQFHZ-UHFFFAOYSA-N 4-[4-(2-cyclobutylsulfanylpyridin-3-yl)-2-methoxyphenoxy]butanoic acid Chemical compound C1=C(OCCCC(O)=O)C(OC)=CC(C=2C(=NC=CC=2)SC2CCC2)=C1 MJVJUFOAXBQFHZ-UHFFFAOYSA-N 0.000 claims 1
- RBISTJBOAXIOLE-UHFFFAOYSA-N 4-[4-(2-cyclobutylsulfanylpyridin-3-yl)phenoxy]butanoic acid Chemical compound C1=CC(OCCCC(=O)O)=CC=C1C1=CC=CN=C1SC1CCC1 RBISTJBOAXIOLE-UHFFFAOYSA-N 0.000 claims 1
- ZBJHSBYKGYSPAI-UHFFFAOYSA-N 4-[4-(2-cyclobutylsulfanylpyridin-3-yl)phenyl]sulfanylbutanoic acid Chemical compound C1=CC(SCCCC(=O)O)=CC=C1C1=CC=CN=C1SC1CCC1 ZBJHSBYKGYSPAI-UHFFFAOYSA-N 0.000 claims 1
- XZLQOQQREACVLP-UHFFFAOYSA-N 4-[4-(2-cyclopentylphenyl)-2,6-difluorophenoxy]butanoic acid Chemical compound C1=C(F)C(OCCCC(=O)O)=C(F)C=C1C1=CC=CC=C1C1CCCC1 XZLQOQQREACVLP-UHFFFAOYSA-N 0.000 claims 1
- DFIHFGOZBHEOCY-UHFFFAOYSA-N 4-[4-(2-cyclopentylsulfanylpyridin-3-yl)-2,6-difluorophenoxy]butanoic acid Chemical compound C1=C(F)C(OCCCC(=O)O)=C(F)C=C1C1=CC=CN=C1SC1CCCC1 DFIHFGOZBHEOCY-UHFFFAOYSA-N 0.000 claims 1
- IYSAIKRRLYIHHV-UHFFFAOYSA-N 4-[4-(2-cyclopentylsulfanylpyridin-3-yl)phenyl]sulfanylbutanoic acid Chemical compound C1=CC(SCCCC(=O)O)=CC=C1C1=CC=CN=C1SC1CCCC1 IYSAIKRRLYIHHV-UHFFFAOYSA-N 0.000 claims 1
- SXJXCPBCENEYIU-UHFFFAOYSA-N 4-[4-(2-propan-2-yloxypyridin-3-yl)phenyl]sulfanylbutanoic acid Chemical compound CC(C)OC1=NC=CC=C1C1=CC=C(SCCCC(O)=O)C=C1 SXJXCPBCENEYIU-UHFFFAOYSA-N 0.000 claims 1
- QBPMSZJWIBFZOV-UHFFFAOYSA-N 4-[4-(2-propan-2-ylsulfanylpyridin-3-yl)phenoxy]butanoic acid Chemical compound CC(C)SC1=NC=CC=C1C1=CC=C(OCCCC(O)=O)C=C1 QBPMSZJWIBFZOV-UHFFFAOYSA-N 0.000 claims 1
- ALJFQNXHRIXUDJ-UHFFFAOYSA-N 4-[4-(2-propylsulfanylpyridin-3-yl)phenoxy]butanoic acid Chemical compound CCCSC1=NC=CC=C1C1=CC=C(OCCCC(O)=O)C=C1 ALJFQNXHRIXUDJ-UHFFFAOYSA-N 0.000 claims 1
- IQZVIWUZGWJZRY-UHFFFAOYSA-N 4-[4-(3-cyclopentyloxyphenyl)-2,3-difluorophenoxy]butanoic acid Chemical compound FC1=C(F)C(OCCCC(=O)O)=CC=C1C1=CC=CC(OC2CCCC2)=C1 IQZVIWUZGWJZRY-UHFFFAOYSA-N 0.000 claims 1
- LJCXBGOVJBEFJN-UHFFFAOYSA-N 4-[4-(3-cyclopentyloxyphenyl)-2,6-difluorophenoxy]butanoic acid Chemical compound C1=C(F)C(OCCCC(=O)O)=C(F)C=C1C1=CC=CC(OC2CCCC2)=C1 LJCXBGOVJBEFJN-UHFFFAOYSA-N 0.000 claims 1
- MJOYMHGPUMCYKV-UHFFFAOYSA-N 4-[4-(6-anilinopyridin-2-yl)-2,6-difluorophenoxy]butanoic acid Chemical compound C1=C(F)C(OCCCC(=O)O)=C(F)C=C1C1=CC=CC(NC=2C=CC=CC=2)=N1 MJOYMHGPUMCYKV-UHFFFAOYSA-N 0.000 claims 1
- GABHFAKWFDYXGZ-UHFFFAOYSA-N 4-[4-(6-cyclobutyloxypyridin-2-yl)-2,6-difluorophenoxy]butanoic acid Chemical compound C1=C(F)C(OCCCC(=O)O)=C(F)C=C1C1=CC=CC(OC2CCC2)=N1 GABHFAKWFDYXGZ-UHFFFAOYSA-N 0.000 claims 1
- KGCHJYQUKOCYLY-UHFFFAOYSA-N 4-[4-(6-cyclobutyloxypyridin-2-yl)-2,6-difluorophenoxy]pentanoic acid Chemical compound C1=C(F)C(OC(CCC(O)=O)C)=C(F)C=C1C1=CC=CC(OC2CCC2)=N1 KGCHJYQUKOCYLY-UHFFFAOYSA-N 0.000 claims 1
- YFIDHWIOSWGBNX-UHFFFAOYSA-N 4-[4-(6-cyclobutyloxypyridin-2-yl)-2,6-difluorophenyl]sulfanylbutanoic acid Chemical compound C1=C(F)C(SCCCC(=O)O)=C(F)C=C1C1=CC=CC(OC2CCC2)=N1 YFIDHWIOSWGBNX-UHFFFAOYSA-N 0.000 claims 1
- IOSBNYCOGFROCD-UHFFFAOYSA-N 4-[4-(6-cyclobutyloxypyridin-2-yl)-2-(trifluoromethyl)phenoxy]butanoic acid Chemical compound C1=C(C(F)(F)F)C(OCCCC(=O)O)=CC=C1C1=CC=CC(OC2CCC2)=N1 IOSBNYCOGFROCD-UHFFFAOYSA-N 0.000 claims 1
- CTALMPONZJZWBR-UHFFFAOYSA-N 4-[4-(6-cyclobutyloxypyridin-2-yl)-2-methylphenoxy]butanoic acid Chemical compound C1=C(OCCCC(O)=O)C(C)=CC(C=2N=C(OC3CCC3)C=CC=2)=C1 CTALMPONZJZWBR-UHFFFAOYSA-N 0.000 claims 1
- CZSVDGKNXJMVON-UHFFFAOYSA-N 4-[4-(6-cyclobutylsulfanylpyridin-2-yl)-2,5-difluorophenoxy]butanoic acid Chemical compound C1=C(F)C(OCCCC(=O)O)=CC(F)=C1C1=CC=CC(SC2CCC2)=N1 CZSVDGKNXJMVON-UHFFFAOYSA-N 0.000 claims 1
- VDZUSUSIKCIACM-UHFFFAOYSA-N 4-[4-(6-cyclobutylsulfanylpyridin-2-yl)phenyl]sulfanylbutanoic acid Chemical compound C1=CC(SCCCC(=O)O)=CC=C1C1=CC=CC(SC2CCC2)=N1 VDZUSUSIKCIACM-UHFFFAOYSA-N 0.000 claims 1
- NFMRDXVZHHGAJL-UHFFFAOYSA-N 4-[4-(6-cyclopentyloxypyridin-2-yl)-2,6-difluorophenoxy]butanoic acid Chemical compound C1=C(F)C(OCCCC(=O)O)=C(F)C=C1C1=CC=CC(OC2CCCC2)=N1 NFMRDXVZHHGAJL-UHFFFAOYSA-N 0.000 claims 1
- MYKQLQNPGMHYIH-UHFFFAOYSA-N 4-[4-(6-cyclopentyloxypyridin-2-yl)-2,6-difluorophenyl]sulfanylbutanoic acid Chemical compound C1=C(F)C(SCCCC(=O)O)=C(F)C=C1C1=CC=CC(OC2CCCC2)=N1 MYKQLQNPGMHYIH-UHFFFAOYSA-N 0.000 claims 1
- ZQWMADBEEHVLNM-UHFFFAOYSA-N 4-[4-(6-cyclopentylsulfanylpyridin-2-yl)-2,6-difluorophenoxy]butanoic acid Chemical compound C1=C(F)C(OCCCC(=O)O)=C(F)C=C1C1=CC=CC(SC2CCCC2)=N1 ZQWMADBEEHVLNM-UHFFFAOYSA-N 0.000 claims 1
- UPZJSXRITNBXGU-UHFFFAOYSA-N 4-[4-(6-cyclopentylsulfanylpyridin-2-yl)-2,6-difluorophenyl]sulfanylbutanoic acid Chemical compound C1=C(F)C(SCCCC(=O)O)=C(F)C=C1C1=CC=CC(SC2CCCC2)=N1 UPZJSXRITNBXGU-UHFFFAOYSA-N 0.000 claims 1
- CBGUPONMMXOXLL-UHFFFAOYSA-N 4-[4-(6-cyclopentylsulfanylpyridin-2-yl)phenyl]sulfanylbutanoic acid Chemical compound C1=CC(SCCCC(=O)O)=CC=C1C1=CC=CC(SC2CCCC2)=N1 CBGUPONMMXOXLL-UHFFFAOYSA-N 0.000 claims 1
- KGRQZDVXKJZHQU-UHFFFAOYSA-N 4-[4-(6-phenoxypyridin-2-yl)phenoxy]butanoic acid Chemical compound C1=CC(OCCCC(=O)O)=CC=C1C1=CC=CC(OC=2C=CC=CC=2)=N1 KGRQZDVXKJZHQU-UHFFFAOYSA-N 0.000 claims 1
- INNXXKGBSIOZPA-UHFFFAOYSA-N 4-[4-(6-propan-2-yloxypyridin-2-yl)phenyl]sulfanylbutanoic acid Chemical compound CC(C)OC1=CC=CC(C=2C=CC(SCCCC(O)=O)=CC=2)=N1 INNXXKGBSIOZPA-UHFFFAOYSA-N 0.000 claims 1
- GQNRQRLRKADICD-UHFFFAOYSA-N 4-[4-(6-propoxypyridin-2-yl)phenyl]sulfanylbutanoic acid Chemical compound CCCOC1=CC=CC(C=2C=CC(SCCCC(O)=O)=CC=2)=N1 GQNRQRLRKADICD-UHFFFAOYSA-N 0.000 claims 1
- XXKSYMIJJQHLKE-UHFFFAOYSA-N 4-[4-[2-(cyclopentylamino)-5-fluorophenyl]-2,6-difluorophenoxy]butanoic acid Chemical compound C1=C(F)C(OCCCC(=O)O)=C(F)C=C1C1=CC(F)=CC=C1NC1CCCC1 XXKSYMIJJQHLKE-UHFFFAOYSA-N 0.000 claims 1
- SBNRGSPPAIDBQJ-UHFFFAOYSA-N 4-[4-[2-(cyclopentylmethyl)pyridin-3-yl]-2,6-difluorophenoxy]butanoic acid Chemical compound C1=C(F)C(OCCCC(=O)O)=C(F)C=C1C1=CC=CN=C1CC1CCCC1 SBNRGSPPAIDBQJ-UHFFFAOYSA-N 0.000 claims 1
- SPZXMLVKWNIZLO-UHFFFAOYSA-N 4-[4-[2-(cyclopropylamino)pyridin-3-yl]-2,6-difluorophenoxy]butanoic acid Chemical compound C1=C(F)C(OCCCC(=O)O)=C(F)C=C1C1=CC=CN=C1NC1CC1 SPZXMLVKWNIZLO-UHFFFAOYSA-N 0.000 claims 1
- LSXTZFGBXVQPBK-UHFFFAOYSA-N 4-[4-[2-(cyclopropylmethoxy)pyridin-3-yl]-2,6-difluorophenoxy]butanoic acid Chemical compound C1=C(F)C(OCCCC(=O)O)=C(F)C=C1C1=CC=CN=C1OCC1CC1 LSXTZFGBXVQPBK-UHFFFAOYSA-N 0.000 claims 1
- MJOVZDZTOYKFRI-UHFFFAOYSA-N 4-[4-[2-(cyclopropylmethylamino)phenyl]-2,6-difluorophenoxy]butanoic acid Chemical compound C1=C(F)C(OCCCC(=O)O)=C(F)C=C1C1=CC=CC=C1NCC1CC1 MJOVZDZTOYKFRI-UHFFFAOYSA-N 0.000 claims 1
- LANGLCYXUFQAMF-UHFFFAOYSA-N 4-[4-[2-(cyclopropylmethylsulfanyl)pyridin-3-yl]-2,6-difluorophenoxy]butanoic acid Chemical compound C1=C(F)C(OCCCC(=O)O)=C(F)C=C1C1=CC=CN=C1SCC1CC1 LANGLCYXUFQAMF-UHFFFAOYSA-N 0.000 claims 1
- ZOEGUEDUJXAOGN-UHFFFAOYSA-N 4-[4-[2-(cyclopropylmethylsulfanyl)pyridin-3-yl]phenoxy]butanoic acid Chemical compound C1=CC(OCCCC(=O)O)=CC=C1C1=CC=CN=C1SCC1CC1 ZOEGUEDUJXAOGN-UHFFFAOYSA-N 0.000 claims 1
- BZAIEPJJTFZOPW-UHFFFAOYSA-N 4-[4-[3-(cyclobutylamino)phenyl]-2,6-difluorophenoxy]butanoic acid Chemical compound C1=C(F)C(OCCCC(=O)O)=C(F)C=C1C1=CC=CC(NC2CCC2)=C1 BZAIEPJJTFZOPW-UHFFFAOYSA-N 0.000 claims 1
- NGUVOERLGAXDSO-UHFFFAOYSA-N 4-[4-[6-(cyclobutylmethyl)pyridin-2-yl]-2,6-difluorophenoxy]butanoic acid Chemical compound C1=C(F)C(OCCCC(=O)O)=C(F)C=C1C1=CC=CC(CC2CCC2)=N1 NGUVOERLGAXDSO-UHFFFAOYSA-N 0.000 claims 1
- YAAJVDLEFZODPP-UHFFFAOYSA-N 4-[4-[6-(cyclopropylmethoxy)pyridin-2-yl]-2,6-difluorophenoxy]butanoic acid Chemical compound C1=C(F)C(OCCCC(=O)O)=C(F)C=C1C1=CC=CC(OCC2CC2)=N1 YAAJVDLEFZODPP-UHFFFAOYSA-N 0.000 claims 1
- CFAHVXGDJQKFAM-UHFFFAOYSA-N 4-[4-[6-(cyclopropylmethylamino)pyridin-2-yl]-2,6-difluorophenoxy]butanoic acid Chemical compound C1=C(F)C(OCCCC(=O)O)=C(F)C=C1C1=CC=CC(NCC2CC2)=N1 CFAHVXGDJQKFAM-UHFFFAOYSA-N 0.000 claims 1
- XPYSWZHGVRFILU-UHFFFAOYSA-N 4-[5-(2-cyclobutylsulfanylpyridin-3-yl)pyridin-2-yl]oxypentanoic acid Chemical compound C1=NC(OC(CCC(O)=O)C)=CC=C1C1=CC=CN=C1SC1CCC1 XPYSWZHGVRFILU-UHFFFAOYSA-N 0.000 claims 1
- DMAJWTXAOKRXPZ-UHFFFAOYSA-N 5-[2-fluoro-4-(2-propan-2-yloxypyridin-3-yl)phenoxy]pentanoic acid Chemical compound CC(C)OC1=NC=CC=C1C1=CC=C(OCCCCC(O)=O)C(F)=C1 DMAJWTXAOKRXPZ-UHFFFAOYSA-N 0.000 claims 1
- XXHSVPLDPVGTHF-UHFFFAOYSA-N 5-[4-(2-cyclopentylsulfanylpyridin-3-yl)-2-fluorophenoxy]pentanoic acid Chemical compound C1=C(F)C(OCCCCC(=O)O)=CC=C1C1=CC=CN=C1SC1CCCC1 XXHSVPLDPVGTHF-UHFFFAOYSA-N 0.000 claims 1
- YUANCYFDXNJEKW-UHFFFAOYSA-N 6-[2,6-difluoro-4-(2-propylsulfanylpyridin-3-yl)phenoxy]hexanoic acid Chemical compound CCCSC1=NC=CC=C1C1=CC(F)=C(OCCCCCC(O)=O)C(F)=C1 YUANCYFDXNJEKW-UHFFFAOYSA-N 0.000 claims 1
- RFHKEVIUFPMOGG-UHFFFAOYSA-N C#CSC1=C(C=CC=N1)C2=CC(=C(C(=C2)F)OCCCC(=O)O)F Chemical compound C#CSC1=C(C=CC=N1)C2=CC(=C(C(=C2)F)OCCCC(=O)O)F RFHKEVIUFPMOGG-UHFFFAOYSA-N 0.000 claims 1
- ZKDCWIQCGIUFDZ-UHFFFAOYSA-N C(C#CC)OC1=NC=CC=C1C1=CC(=C(OCCCC(=O)O)C(=C1)F)F Chemical compound C(C#CC)OC1=NC=CC=C1C1=CC(=C(OCCCC(=O)O)C(=C1)F)F ZKDCWIQCGIUFDZ-UHFFFAOYSA-N 0.000 claims 1
- JMRUOOKQDMCBAW-UHFFFAOYSA-N C(C)(C)(C)SC1=NC=CC=C1C1=CC(=C(OCCCC(=O)O)C(=C1)F)F Chemical compound C(C)(C)(C)SC1=NC=CC=C1C1=CC(=C(OCCCC(=O)O)C(=C1)F)F JMRUOOKQDMCBAW-UHFFFAOYSA-N 0.000 claims 1
- ULGCEMPXGMCGJS-UHFFFAOYSA-N C(C)(C)NC1=C(C=CC=C1)C1=CC=C(OCCCC(=O)O)C=C1 Chemical compound C(C)(C)NC1=C(C=CC=C1)C1=CC=C(OCCCC(=O)O)C=C1 ULGCEMPXGMCGJS-UHFFFAOYSA-N 0.000 claims 1
- NNDSBJFAXIQWRM-UHFFFAOYSA-N C(C)(C)OC1=NC=CC=C1C1=CC=C(C=C1)SC(CCC(=O)O)C Chemical compound C(C)(C)OC1=NC=CC=C1C1=CC=C(C=C1)SC(CCC(=O)O)C NNDSBJFAXIQWRM-UHFFFAOYSA-N 0.000 claims 1
- QAZARCQYAYGSCI-UHFFFAOYSA-N C(C)(C)OC1=NC=CC=C1C1=CC=C(C=C1)SCCCCC(=O)O Chemical compound C(C)(C)OC1=NC=CC=C1C1=CC=C(C=C1)SCCCCC(=O)O QAZARCQYAYGSCI-UHFFFAOYSA-N 0.000 claims 1
- XSMVITSQILLGJC-UHFFFAOYSA-N C(C)(C)SC1=CC=CC(=N1)C1=CC=C(OCCCC(=O)O)C=C1 Chemical compound C(C)(C)SC1=CC=CC(=N1)C1=CC=C(OCCCC(=O)O)C=C1 XSMVITSQILLGJC-UHFFFAOYSA-N 0.000 claims 1
- BPCFIEZEMULLQK-UHFFFAOYSA-N C(C)(C)SC1=NC=CC=C1C1=CC=C(C=C1)SCCCC(=O)O Chemical compound C(C)(C)SC1=NC=CC=C1C1=CC=C(C=C1)SCCCC(=O)O BPCFIEZEMULLQK-UHFFFAOYSA-N 0.000 claims 1
- GINGROLQJMREFT-UHFFFAOYSA-N C(CC)NC1=C(C=CC=C1)C1=CC=C(OCCCC(=O)O)C=C1 Chemical compound C(CC)NC1=C(C=CC=C1)C1=CC=C(OCCCC(=O)O)C=C1 GINGROLQJMREFT-UHFFFAOYSA-N 0.000 claims 1
- NMEAMTYWUAVPPP-UHFFFAOYSA-N C(CCC)SC1=NC=CC=C1C1=CC(=C(OCCCC(=O)O)C(=C1)F)F Chemical compound C(CCC)SC1=NC=CC=C1C1=CC(=C(OCCCC(=O)O)C(=C1)F)F NMEAMTYWUAVPPP-UHFFFAOYSA-N 0.000 claims 1
- GVFBISVPUDKWML-UHFFFAOYSA-N C1(CC1)CNC1=C(C=CC=C1)C1=CC=C(OCCCC(=O)O)C=C1 Chemical compound C1(CC1)CNC1=C(C=CC=C1)C1=CC=C(OCCCC(=O)O)C=C1 GVFBISVPUDKWML-UHFFFAOYSA-N 0.000 claims 1
- MBEDVVJPCMIDKN-UHFFFAOYSA-N C1(CC1)CNC1=NC=CC=C1C1=CC(=C(OCCCC(=O)O)C(=C1)F)F Chemical compound C1(CC1)CNC1=NC=CC=C1C1=CC(=C(OCCCC(=O)O)C(=C1)F)F MBEDVVJPCMIDKN-UHFFFAOYSA-N 0.000 claims 1
- OAIDWRNGRAXPIJ-UHFFFAOYSA-N C1(CC1)CNC=1C=C(C=CC1)C1=CC(=C(OCCCC(=O)O)C(=C1)F)F Chemical compound C1(CC1)CNC=1C=C(C=CC1)C1=CC(=C(OCCCC(=O)O)C(=C1)F)F OAIDWRNGRAXPIJ-UHFFFAOYSA-N 0.000 claims 1
- DVWCRJXYQWYXSR-UHFFFAOYSA-N C1(CC1)COC1=CC=CC(=N1)C1=CC(=C(C(=C1)F)SCCCC(=O)O)F Chemical compound C1(CC1)COC1=CC=CC(=N1)C1=CC(=C(C(=C1)F)SCCCC(=O)O)F DVWCRJXYQWYXSR-UHFFFAOYSA-N 0.000 claims 1
- BYCNLHJICUABTM-UHFFFAOYSA-N C1(CC1)COC1=NC=CC=C1C1=CC(=C(C(=C1)F)SCCCC(=O)O)F Chemical compound C1(CC1)COC1=NC=CC=C1C1=CC(=C(C(=C1)F)SCCCC(=O)O)F BYCNLHJICUABTM-UHFFFAOYSA-N 0.000 claims 1
- HDHUJXFWXWZVFM-UHFFFAOYSA-N C1(CC1)COC1=NC=CC=C1C1=CC=C(C=C1)SCCCC(=O)O Chemical compound C1(CC1)COC1=NC=CC=C1C1=CC=C(C=C1)SCCCC(=O)O HDHUJXFWXWZVFM-UHFFFAOYSA-N 0.000 claims 1
- FDKQYNJDRATRBJ-UHFFFAOYSA-N C1(CC1)CSC1=CC=CC(=N1)C1=CC(=C(OCCCC(=O)O)C(=C1)F)F Chemical compound C1(CC1)CSC1=CC=CC(=N1)C1=CC(=C(OCCCC(=O)O)C(=C1)F)F FDKQYNJDRATRBJ-UHFFFAOYSA-N 0.000 claims 1
- XNUSYMIFYJLPPW-UHFFFAOYSA-N C1(CC1)OC1=NC=CC=C1C1=CC(=C(OCCCCC(=O)O)C(=C1)F)F Chemical compound C1(CC1)OC1=NC=CC=C1C1=CC(=C(OCCCCC(=O)O)C(=C1)F)F XNUSYMIFYJLPPW-UHFFFAOYSA-N 0.000 claims 1
- HERXCDFUOCTTBE-UHFFFAOYSA-N C1(CC1)SC1=NC=CC=C1C1=CC(=C(OCCCC(=O)O)C(=C1)F)F Chemical compound C1(CC1)SC1=NC=CC=C1C1=CC(=C(OCCCC(=O)O)C(=C1)F)F HERXCDFUOCTTBE-UHFFFAOYSA-N 0.000 claims 1
- WSZOGZYQCOYMOV-UHFFFAOYSA-N C1(CCC1)CC1=C(C=CC=C1)C1=CC(=C(OCCCC(=O)O)C(=C1)F)F Chemical compound C1(CCC1)CC1=C(C=CC=C1)C1=CC(=C(OCCCC(=O)O)C(=C1)F)F WSZOGZYQCOYMOV-UHFFFAOYSA-N 0.000 claims 1
- UDKVYFSSBAUEQX-UHFFFAOYSA-N C1(CCC1)CC=1C=C(C=CC1)C1=CC(=C(OCCCC(=O)O)C(=C1)F)F Chemical compound C1(CCC1)CC=1C=C(C=CC1)C1=CC(=C(OCCCC(=O)O)C(=C1)F)F UDKVYFSSBAUEQX-UHFFFAOYSA-N 0.000 claims 1
- CELWJCYTGIQOSA-UHFFFAOYSA-N C1(CCC1)COC1=NC=CC=C1C1=CC(=C(C(=C1)F)SCCCCC(=O)O)F Chemical compound C1(CCC1)COC1=NC=CC=C1C1=CC(=C(C(=C1)F)SCCCCC(=O)O)F CELWJCYTGIQOSA-UHFFFAOYSA-N 0.000 claims 1
- MAKFOXBSQMOZQJ-UHFFFAOYSA-N C1(CCC1)COC1=NC=CC=C1C1=CC(=C(OCCCCC(=O)O)C(=C1)F)F Chemical compound C1(CCC1)COC1=NC=CC=C1C1=CC(=C(OCCCCC(=O)O)C(=C1)F)F MAKFOXBSQMOZQJ-UHFFFAOYSA-N 0.000 claims 1
- JEGXYDADDATKRF-UHFFFAOYSA-N C1(CCC1)CSC1=NC=CC=C1C1=CC(=C(OCCCC(=O)O)C(=C1)F)F Chemical compound C1(CCC1)CSC1=NC=CC=C1C1=CC(=C(OCCCC(=O)O)C(=C1)F)F JEGXYDADDATKRF-UHFFFAOYSA-N 0.000 claims 1
- PIAAQHKJXLDWMR-UHFFFAOYSA-N C1(CCC1)NC1=C(C=CC=C1)C1=CC(=C(OCCCC(=O)O)C(=C1)F)F Chemical compound C1(CCC1)NC1=C(C=CC=C1)C1=CC(=C(OCCCC(=O)O)C(=C1)F)F PIAAQHKJXLDWMR-UHFFFAOYSA-N 0.000 claims 1
- VNOXIQLTHAKMBA-UHFFFAOYSA-N C1(CCC1)NC1=C(C=CC=C1)C1=CC=C(OCCCC(=O)O)C=C1 Chemical compound C1(CCC1)NC1=C(C=CC=C1)C1=CC=C(OCCCC(=O)O)C=C1 VNOXIQLTHAKMBA-UHFFFAOYSA-N 0.000 claims 1
- JVSUHNLAUYTHNG-UHFFFAOYSA-N C1(CCC1)OC1=CC=CC(=N1)C1=CC=C(C=C1)SCCCC(=O)O Chemical compound C1(CCC1)OC1=CC=CC(=N1)C1=CC=C(C=C1)SCCCC(=O)O JVSUHNLAUYTHNG-UHFFFAOYSA-N 0.000 claims 1
- JSFAWTBNWDYZEO-UHFFFAOYSA-N C1(CCC1)OC1=NC=CC=C1C1=CC(=C(C(=C1)F)SCCCC(=O)O)F Chemical compound C1(CCC1)OC1=NC=CC=C1C1=CC(=C(C(=C1)F)SCCCC(=O)O)F JSFAWTBNWDYZEO-UHFFFAOYSA-N 0.000 claims 1
- ZUNFJHWCPUBVNV-UHFFFAOYSA-N C1(CCC1)OC1=NC=CC=C1C1=CC(=C(C(=C1)F)SCCCCC(=O)O)F Chemical compound C1(CCC1)OC1=NC=CC=C1C1=CC(=C(C(=C1)F)SCCCCC(=O)O)F ZUNFJHWCPUBVNV-UHFFFAOYSA-N 0.000 claims 1
- LYFDVDVGNVZSCK-UHFFFAOYSA-N C1(CCC1)OC1=NC=CC=C1C1=CC(=C(OCCCC(=O)O)C(=C1)F)F Chemical compound C1(CCC1)OC1=NC=CC=C1C1=CC(=C(OCCCC(=O)O)C(=C1)F)F LYFDVDVGNVZSCK-UHFFFAOYSA-N 0.000 claims 1
- HRUNVYWWYVNTPO-UHFFFAOYSA-N C1(CCC1)OC1=NC=CC=C1C1=CC(=C(OCCCCCC(=O)O)C(=C1)F)F Chemical compound C1(CCC1)OC1=NC=CC=C1C1=CC(=C(OCCCCCC(=O)O)C(=C1)F)F HRUNVYWWYVNTPO-UHFFFAOYSA-N 0.000 claims 1
- HQRDXRVRNFFTJR-UHFFFAOYSA-N C1(CCC1)OC=1C=C(C=CC1)C1=CC=C(C=N1)OCCCC(=O)O Chemical compound C1(CCC1)OC=1C=C(C=CC1)C1=CC=C(C=N1)OCCCC(=O)O HQRDXRVRNFFTJR-UHFFFAOYSA-N 0.000 claims 1
- AQYZYKGRYNGALN-UHFFFAOYSA-N C1(CCC1)SC1=CC=CC(=N1)C1=CC(=C(C(=C1)F)SCCCC(=O)O)F Chemical compound C1(CCC1)SC1=CC=CC(=N1)C1=CC(=C(C(=C1)F)SCCCC(=O)O)F AQYZYKGRYNGALN-UHFFFAOYSA-N 0.000 claims 1
- NVEYDINNXSQLES-UHFFFAOYSA-N C1(CCC1)SC1=CC=CC(=N1)C1=CC(=C(C=C1)SCCCC(=O)O)F Chemical compound C1(CCC1)SC1=CC=CC(=N1)C1=CC(=C(C=C1)SCCCC(=O)O)F NVEYDINNXSQLES-UHFFFAOYSA-N 0.000 claims 1
- YISCBKKBETZYGJ-UHFFFAOYSA-N C1(CCC1)SC1=NC=CC=C1C1=C(C=C(OCCCC(=O)O)C=C1F)F Chemical compound C1(CCC1)SC1=NC=CC=C1C1=C(C=C(OCCCC(=O)O)C=C1F)F YISCBKKBETZYGJ-UHFFFAOYSA-N 0.000 claims 1
- WMRRMHRPPNHOBV-UHFFFAOYSA-N C1(CCC1)SC1=NC=CC=C1C1=CC(=C(C(=C1)F)SCCCCCC(=O)O)F Chemical compound C1(CCC1)SC1=NC=CC=C1C1=CC(=C(C(=C1)F)SCCCCCC(=O)O)F WMRRMHRPPNHOBV-UHFFFAOYSA-N 0.000 claims 1
- UFSJYNCHOSVKOY-UHFFFAOYSA-N C1(CCC1)SC1=NC=CC=C1C1=CC(=C(OCC2C(C2)C(=O)O)C(=C1)F)F Chemical compound C1(CCC1)SC1=NC=CC=C1C1=CC(=C(OCC2C(C2)C(=O)O)C(=C1)F)F UFSJYNCHOSVKOY-UHFFFAOYSA-N 0.000 claims 1
- UHWRRMOHVHHUJL-UHFFFAOYSA-N C1(CCC1)SC1=NC=CC=C1C1=CC(=C(OCCC(C(=O)O)C)C(=C1)F)F Chemical compound C1(CCC1)SC1=NC=CC=C1C1=CC(=C(OCCC(C(=O)O)C)C(=C1)F)F UHWRRMOHVHHUJL-UHFFFAOYSA-N 0.000 claims 1
- CYABGDCQUJSUIV-UHFFFAOYSA-N C1(CCC1)SC1=NC=CC=C1C1=CC(=C(OCCCCC(=O)O)C=C1)F Chemical compound C1(CCC1)SC1=NC=CC=C1C1=CC(=C(OCCCCC(=O)O)C=C1)F CYABGDCQUJSUIV-UHFFFAOYSA-N 0.000 claims 1
- JSIKEOKHJKPVJG-UHFFFAOYSA-N C1(CCC1)SC1=NC=CC=C1C1=CC(=C(OCCCCCC(=O)O)C(=C1)F)F Chemical compound C1(CCC1)SC1=NC=CC=C1C1=CC(=C(OCCCCCC(=O)O)C(=C1)F)F JSIKEOKHJKPVJG-UHFFFAOYSA-N 0.000 claims 1
- FSDIHQFPBKXMSF-GFCCVEGCSA-N C1(CCC1)SC1=NC=CC=C1C1=CC(=C(O[C@@H](CCC(=O)O)C)C(=C1)F)F Chemical compound C1(CCC1)SC1=NC=CC=C1C1=CC(=C(O[C@@H](CCC(=O)O)C)C(=C1)F)F FSDIHQFPBKXMSF-GFCCVEGCSA-N 0.000 claims 1
- GPFHICAQEISDMF-UHFFFAOYSA-N C1(CCC1)SC1=NC=CC=C1C1=CC=C(C=C1)SCCCCC(=O)O Chemical compound C1(CCC1)SC1=NC=CC=C1C1=CC=C(C=C1)SCCCCC(=O)O GPFHICAQEISDMF-UHFFFAOYSA-N 0.000 claims 1
- AIBOLCZOQGCAHH-UHFFFAOYSA-N C1(CCCC1)C1=CC=CC(=N1)C1=CC(=C(OCCCC(=O)O)C(=C1)F)F Chemical compound C1(CCCC1)C1=CC=CC(=N1)C1=CC(=C(OCCCC(=O)O)C(=C1)F)F AIBOLCZOQGCAHH-UHFFFAOYSA-N 0.000 claims 1
- JXHHAFHQIXPNSZ-UHFFFAOYSA-N C1(CCCC1)C1=NC=CC=C1C1=CC(=C(OCCCC(=O)O)C(=C1)F)F Chemical compound C1(CCCC1)C1=NC=CC=C1C1=CC(=C(OCCCC(=O)O)C(=C1)F)F JXHHAFHQIXPNSZ-UHFFFAOYSA-N 0.000 claims 1
- XPXLCGWSOAGCMR-UHFFFAOYSA-N C1(CCCC1)CC1=C(C=CC=C1)C1=CC(=C(OCCCC(=O)O)C(=C1)F)F Chemical compound C1(CCCC1)CC1=C(C=CC=C1)C1=CC(=C(OCCCC(=O)O)C(=C1)F)F XPXLCGWSOAGCMR-UHFFFAOYSA-N 0.000 claims 1
- DMKXMMPWFSGDGR-UHFFFAOYSA-N C1(CCCC1)CC1=CC=CC(=N1)C1=CC(=C(OCCCC(=O)O)C(=C1)F)F Chemical compound C1(CCCC1)CC1=CC=CC(=N1)C1=CC(=C(OCCCC(=O)O)C(=C1)F)F DMKXMMPWFSGDGR-UHFFFAOYSA-N 0.000 claims 1
- MFHAMKZNDYQDCH-UHFFFAOYSA-N C1(CCCC1)NC1=C(C=CC=C1)C1=CC(=C(OCCCC(=O)O)C(=C1)F)F Chemical compound C1(CCCC1)NC1=C(C=CC=C1)C1=CC(=C(OCCCC(=O)O)C(=C1)F)F MFHAMKZNDYQDCH-UHFFFAOYSA-N 0.000 claims 1
- DPZAUVQLOSLBRJ-UHFFFAOYSA-N C1(CCCC1)NC1=C(C=CC=C1)C1=CC=C(OCCCC(=O)O)C=C1 Chemical compound C1(CCCC1)NC1=C(C=CC=C1)C1=CC=C(OCCCC(=O)O)C=C1 DPZAUVQLOSLBRJ-UHFFFAOYSA-N 0.000 claims 1
- NXUKMQCBXOBNLM-UHFFFAOYSA-N C1(CCCC1)NC1=CC=CC(=N1)C1=CC(=C(OCCCC(=O)O)C(=C1)F)F Chemical compound C1(CCCC1)NC1=CC=CC(=N1)C1=CC(=C(OCCCC(=O)O)C(=C1)F)F NXUKMQCBXOBNLM-UHFFFAOYSA-N 0.000 claims 1
- VGHGDBOAXXCHLZ-UHFFFAOYSA-N C1(CCCC1)NC1=NC=CC=C1C1=CC(=C(C=C1)SCCCC(=O)O)F Chemical compound C1(CCCC1)NC1=NC=CC=C1C1=CC(=C(C=C1)SCCCC(=O)O)F VGHGDBOAXXCHLZ-UHFFFAOYSA-N 0.000 claims 1
- FFLDQGGDRNPRRT-UHFFFAOYSA-N C1(CCCC1)NC=1C=C(C=CC1)C1=CC(=C(OCCCC(=O)O)C(=C1)F)F Chemical compound C1(CCCC1)NC=1C=C(C=CC1)C1=CC(=C(OCCCC(=O)O)C(=C1)F)F FFLDQGGDRNPRRT-UHFFFAOYSA-N 0.000 claims 1
- SBRLTDUZTVTFOW-UHFFFAOYSA-N C1(CCCC1)OC1=CC=CC(=N1)C1=CC=C(C=C1)SCCCC(=O)O Chemical compound C1(CCCC1)OC1=CC=CC(=N1)C1=CC=C(C=C1)SCCCC(=O)O SBRLTDUZTVTFOW-UHFFFAOYSA-N 0.000 claims 1
- DZCVKGSYHVBNCV-UHFFFAOYSA-N C1(CCCC1)OC1=NC(=CC=C1C1=CC(=C(C=C1)SCCCC(=O)O)F)C Chemical compound C1(CCCC1)OC1=NC(=CC=C1C1=CC(=C(C=C1)SCCCC(=O)O)F)C DZCVKGSYHVBNCV-UHFFFAOYSA-N 0.000 claims 1
- RTFBQUAJECGYPI-UHFFFAOYSA-N C1(CCCC1)OC1=NC=C(C=C1C1=CC(=C(C(=C1)F)SCCCC(=O)O)F)C Chemical compound C1(CCCC1)OC1=NC=C(C=C1C1=CC(=C(C(=C1)F)SCCCC(=O)O)F)C RTFBQUAJECGYPI-UHFFFAOYSA-N 0.000 claims 1
- KLFHDBDAXFJGBH-UHFFFAOYSA-N C1(CCCC1)OC1=NC=C(C=C1C1=CC(=C(C=C1)SCCCC(=O)O)F)C Chemical compound C1(CCCC1)OC1=NC=C(C=C1C1=CC(=C(C=C1)SCCCC(=O)O)F)C KLFHDBDAXFJGBH-UHFFFAOYSA-N 0.000 claims 1
- KSCHYCNDOMEWRW-UHFFFAOYSA-N C1(CCCC1)OC1=NC=C(C=C1C1=CC(=C(OCCCC(=O)O)C(=C1)F)F)C Chemical compound C1(CCCC1)OC1=NC=C(C=C1C1=CC(=C(OCCCC(=O)O)C(=C1)F)F)C KSCHYCNDOMEWRW-UHFFFAOYSA-N 0.000 claims 1
- YRSQUTQDMVUUNL-UHFFFAOYSA-N C1(CCCC1)OC1=NC=C(C=C1C1=CC=C(C=C1)SCCCC(=O)O)C Chemical compound C1(CCCC1)OC1=NC=C(C=C1C1=CC=C(C=C1)SCCCC(=O)O)C YRSQUTQDMVUUNL-UHFFFAOYSA-N 0.000 claims 1
- DDWWJXGSBFASMA-UHFFFAOYSA-N C1(CCCC1)OC1=NC=CC=C1C1=CC(=C(C(=C1)F)SC(CCC(=O)O)C)F Chemical compound C1(CCCC1)OC1=NC=CC=C1C1=CC(=C(C(=C1)F)SC(CCC(=O)O)C)F DDWWJXGSBFASMA-UHFFFAOYSA-N 0.000 claims 1
- LSOXASSMFCHZKH-UHFFFAOYSA-N C1(CCCC1)OC1=NC=CC=C1C1=CC(=C(C(=C1)F)SCCCC(=O)O)F Chemical compound C1(CCCC1)OC1=NC=CC=C1C1=CC(=C(C(=C1)F)SCCCC(=O)O)F LSOXASSMFCHZKH-UHFFFAOYSA-N 0.000 claims 1
- OFGHWNDIFVOGSO-UHFFFAOYSA-N C1(CCCC1)OC1=NC=CC=C1C1=CC(=C(C(=C1)F)SCCCCC(=O)O)F Chemical compound C1(CCCC1)OC1=NC=CC=C1C1=CC(=C(C(=C1)F)SCCCCC(=O)O)F OFGHWNDIFVOGSO-UHFFFAOYSA-N 0.000 claims 1
- NWDPJWVZWBUVFS-UHFFFAOYSA-N C1(CCCC1)OC1=NC=CC=C1C1=CC(=C(C(=C1)F)SCCCCCC(=O)O)F Chemical compound C1(CCCC1)OC1=NC=CC=C1C1=CC(=C(C(=C1)F)SCCCCCC(=O)O)F NWDPJWVZWBUVFS-UHFFFAOYSA-N 0.000 claims 1
- VMAKNNZITDPJJV-UHFFFAOYSA-N C1(CCCC1)OC1=NC=CC=C1C1=CC(=C(C=C1)SCCCC(=O)O)F Chemical compound C1(CCCC1)OC1=NC=CC=C1C1=CC(=C(C=C1)SCCCC(=O)O)F VMAKNNZITDPJJV-UHFFFAOYSA-N 0.000 claims 1
- IXMLSBAXBRVKOZ-UHFFFAOYSA-N C1(CCCC1)OC1=NC=CC=C1C1=CC(=C(OCCCC(=O)O)C(=C1)F)F Chemical compound C1(CCCC1)OC1=NC=CC=C1C1=CC(=C(OCCCC(=O)O)C(=C1)F)F IXMLSBAXBRVKOZ-UHFFFAOYSA-N 0.000 claims 1
- MHYCPXIBIJUBOZ-UHFFFAOYSA-N C1(CCCC1)OC1=NC=CC=C1C1=CC(=C(OCCCCC(=O)O)C=C1)F Chemical compound C1(CCCC1)OC1=NC=CC=C1C1=CC(=C(OCCCCC(=O)O)C=C1)F MHYCPXIBIJUBOZ-UHFFFAOYSA-N 0.000 claims 1
- BYPFGXVGBNDXEX-UHFFFAOYSA-N C1(CCCC1)OC1=NC=CC=C1C1=CC(=C(OCCCCCC(=O)O)C(=C1)F)F Chemical compound C1(CCCC1)OC1=NC=CC=C1C1=CC(=C(OCCCCCC(=O)O)C(=C1)F)F BYPFGXVGBNDXEX-UHFFFAOYSA-N 0.000 claims 1
- SSAGMLQQTDKVAR-UHFFFAOYSA-N C1(CCCC1)OC1=NC=CC=C1C1=CC(=C(OCCCCCCC(=O)O)C(=C1)F)F Chemical compound C1(CCCC1)OC1=NC=CC=C1C1=CC(=C(OCCCCCCC(=O)O)C(=C1)F)F SSAGMLQQTDKVAR-UHFFFAOYSA-N 0.000 claims 1
- ZVRWCBOLUCMNPF-UHFFFAOYSA-N C1(CCCC1)OC1=NC=CC=C1C1=CC=C(C=C1)SC(CCC(=O)O)C Chemical compound C1(CCCC1)OC1=NC=CC=C1C1=CC=C(C=C1)SC(CCC(=O)O)C ZVRWCBOLUCMNPF-UHFFFAOYSA-N 0.000 claims 1
- DNQNJGFJCLXKPI-UHFFFAOYSA-N C1(CCCC1)OC1=NC=CC=C1C1=CC=C(C=C1)SCCCC(=O)O Chemical compound C1(CCCC1)OC1=NC=CC=C1C1=CC=C(C=C1)SCCCC(=O)O DNQNJGFJCLXKPI-UHFFFAOYSA-N 0.000 claims 1
- CVDPJAXSOPHNKP-UHFFFAOYSA-N C1(CCCC1)SC1=NC=CC=C1C1=CC(=C(C(=C1)F)SC(CCC(=O)O)C)F Chemical compound C1(CCCC1)SC1=NC=CC=C1C1=CC(=C(C(=C1)F)SC(CCC(=O)O)C)F CVDPJAXSOPHNKP-UHFFFAOYSA-N 0.000 claims 1
- PNTQOXIHMGFZSF-UHFFFAOYSA-N C1(CCCC1)SC1=NC=CC=C1C1=CC(=C(C(=C1)F)SCCCC(=O)O)F Chemical compound C1(CCCC1)SC1=NC=CC=C1C1=CC(=C(C(=C1)F)SCCCC(=O)O)F PNTQOXIHMGFZSF-UHFFFAOYSA-N 0.000 claims 1
- ARSLGTHGRQHSTI-UHFFFAOYSA-N C1(CCCC1)SC1=NC=CC=C1C1=CC(=C(C(=C1)F)SCCCCC(=O)O)F Chemical compound C1(CCCC1)SC1=NC=CC=C1C1=CC(=C(C(=C1)F)SCCCCC(=O)O)F ARSLGTHGRQHSTI-UHFFFAOYSA-N 0.000 claims 1
- SJSRGDOHGUDRQN-UHFFFAOYSA-N C1(CCCC1)SC1=NC=CC=C1C1=CC(=C(C(=C1)F)SCCCCCC(=O)O)F Chemical compound C1(CCCC1)SC1=NC=CC=C1C1=CC(=C(C(=C1)F)SCCCCCC(=O)O)F SJSRGDOHGUDRQN-UHFFFAOYSA-N 0.000 claims 1
- OCVKTLJGQOETQE-UHFFFAOYSA-N C1(CCCC1)SC1=NC=CC=C1C1=CC(=C(C=C1)SCCCC(=O)O)F Chemical compound C1(CCCC1)SC1=NC=CC=C1C1=CC(=C(C=C1)SCCCC(=O)O)F OCVKTLJGQOETQE-UHFFFAOYSA-N 0.000 claims 1
- TVFAXLLRFCUKMD-UHFFFAOYSA-N C1(CCCC1)SC1=NC=CC=C1C1=CC(=C(OCCCCCC(=O)O)C(=C1)F)F Chemical compound C1(CCCC1)SC1=NC=CC=C1C1=CC(=C(OCCCCCC(=O)O)C(=C1)F)F TVFAXLLRFCUKMD-UHFFFAOYSA-N 0.000 claims 1
- GCBDODGWYWRTFC-CYBMUJFWSA-N C1(CCCC1)SC1=NC=CC=C1C1=CC(=C(O[C@@H](CCC(=O)O)C)C(=C1)F)F Chemical compound C1(CCCC1)SC1=NC=CC=C1C1=CC(=C(O[C@@H](CCC(=O)O)C)C(=C1)F)F GCBDODGWYWRTFC-CYBMUJFWSA-N 0.000 claims 1
- ZDIWOYHKKHFLIZ-UHFFFAOYSA-N C1(CCCC1)SC1=NC=CC=C1C1=CC=C(C=C1)SCCCCC(=O)O Chemical compound C1(CCCC1)SC1=NC=CC=C1C1=CC=C(C=C1)SCCCCC(=O)O ZDIWOYHKKHFLIZ-UHFFFAOYSA-N 0.000 claims 1
- IFNSJZCCQQTDMQ-UHFFFAOYSA-N C1(CCCC1)SC1=NC=CC=C1C1=CC=C(OCCCC(=O)O)C=C1 Chemical compound C1(CCCC1)SC1=NC=CC=C1C1=CC=C(OCCCC(=O)O)C=C1 IFNSJZCCQQTDMQ-UHFFFAOYSA-N 0.000 claims 1
- SCRBIHAODMCBIG-UHFFFAOYSA-N CCC(C)SC1=C(C=CC=N1)C2=CC(=C(C(=C2)C)OCCCC(=O)O)C Chemical compound CCC(C)SC1=C(C=CC=N1)C2=CC(=C(C(=C2)C)OCCCC(=O)O)C SCRBIHAODMCBIG-UHFFFAOYSA-N 0.000 claims 1
- SXAJORRZXORHKJ-UHFFFAOYSA-N CN(C1CN(CC1)C1=CC=CC(=N1)C1=CC(=C(OCCCC(=O)O)C(=C1)F)F)C Chemical compound CN(C1CN(CC1)C1=CC=CC(=N1)C1=CC(=C(OCCCC(=O)O)C(=C1)F)F)C SXAJORRZXORHKJ-UHFFFAOYSA-N 0.000 claims 1
- HAIIHJRSWNVKOI-UHFFFAOYSA-N CN(CCOC1=NC=CC=C1C1=CC(=C(OCCCC(=O)O)C(=C1)F)F)C Chemical compound CN(CCOC1=NC=CC=C1C1=CC(=C(OCCCC(=O)O)C(=C1)F)F)C HAIIHJRSWNVKOI-UHFFFAOYSA-N 0.000 claims 1
- YNKDCLJEWRHYGU-UHFFFAOYSA-N ClC=1C=CC(=C(C1)C1=CC(=C(OCCCC(=O)O)C(=C1)F)F)NC1CCCC1 Chemical compound ClC=1C=CC(=C(C1)C1=CC(=C(OCCCC(=O)O)C(=C1)F)F)NC1CCCC1 YNKDCLJEWRHYGU-UHFFFAOYSA-N 0.000 claims 1
- ZBXFYLPCGDLYCT-UHFFFAOYSA-N FC1=C(C(=CC(=C1)C1=NC(=CC=C1)OCCC)F)SCCCC(=O)O Chemical compound FC1=C(C(=CC(=C1)C1=NC(=CC=C1)OCCC)F)SCCCC(=O)O ZBXFYLPCGDLYCT-UHFFFAOYSA-N 0.000 claims 1
- UKEOKAUKHBZZGU-UHFFFAOYSA-N FC1=C(C(=CC(=C1)C1=NC(=CC=C1)SCCC)F)SCCCC(=O)O Chemical compound FC1=C(C(=CC(=C1)C1=NC(=CC=C1)SCCC)F)SCCCC(=O)O UKEOKAUKHBZZGU-UHFFFAOYSA-N 0.000 claims 1
- AZWKOKDHOGQYEV-UHFFFAOYSA-N FC1=C(C(=CC(=C1)C=1C(=NC=CC1)OC(C)C)F)SCCCC(=O)O Chemical compound FC1=C(C(=CC(=C1)C=1C(=NC=CC1)OC(C)C)F)SCCCC(=O)O AZWKOKDHOGQYEV-UHFFFAOYSA-N 0.000 claims 1
- LKONJPJHXBTOTJ-UHFFFAOYSA-N FC1=C(C(=CC(=C1)C=1C(=NC=CC1)OC(C)C)F)SCCCCC(=O)O Chemical compound FC1=C(C(=CC(=C1)C=1C(=NC=CC1)OC(C)C)F)SCCCCC(=O)O LKONJPJHXBTOTJ-UHFFFAOYSA-N 0.000 claims 1
- WHIHDUPXASLPQO-UHFFFAOYSA-N FC1=C(C(=CC(=C1)C=1C(=NC=CC1)SC(C)C)F)SCCCC(=O)O Chemical compound FC1=C(C(=CC(=C1)C=1C(=NC=CC1)SC(C)C)F)SCCCC(=O)O WHIHDUPXASLPQO-UHFFFAOYSA-N 0.000 claims 1
- WBHTVVQWQXDBJP-UHFFFAOYSA-N FC1=C(C(=CC(=C1)C=1C(=NC=CC1)SCCC)F)SCCCC(=O)O Chemical compound FC1=C(C(=CC(=C1)C=1C(=NC=CC1)SCCC)F)SCCCC(=O)O WBHTVVQWQXDBJP-UHFFFAOYSA-N 0.000 claims 1
- VZSRICJBSKBLSO-UHFFFAOYSA-N FC1=C(C(=CC(=C1)C=1C(=NC=CC1)SCCC)F)SCCCCC(=O)O Chemical compound FC1=C(C(=CC(=C1)C=1C(=NC=CC1)SCCC)F)SCCCCC(=O)O VZSRICJBSKBLSO-UHFFFAOYSA-N 0.000 claims 1
- IKQYEDGLNKBFLE-UHFFFAOYSA-N FC1=C(C(=CC(=C1)C=1C(=NC=CC1)SCCC)F)SCCCCCC(=O)O Chemical compound FC1=C(C(=CC(=C1)C=1C(=NC=CC1)SCCC)F)SCCCCCC(=O)O IKQYEDGLNKBFLE-UHFFFAOYSA-N 0.000 claims 1
- BZSSPYKGBNJMMH-UHFFFAOYSA-N FC1=C(C=CC(=C1)C=1C(=NC=C(C1)C)OC(C)C)SCCCC(=O)O Chemical compound FC1=C(C=CC(=C1)C=1C(=NC=C(C1)C)OC(C)C)SCCCC(=O)O BZSSPYKGBNJMMH-UHFFFAOYSA-N 0.000 claims 1
- BVISHEDQRHTIIX-UHFFFAOYSA-N FC1=C(C=CC(=C1)C=1C(=NC=CC1)NC(C)C)SCCCC(=O)O Chemical compound FC1=C(C=CC(=C1)C=1C(=NC=CC1)NC(C)C)SCCCC(=O)O BVISHEDQRHTIIX-UHFFFAOYSA-N 0.000 claims 1
- VOPOFCCMXIBNSU-UHFFFAOYSA-N FC1=C(C=CC(=C1)C=1C(=NC=CC1)OC(C)C)SCCCC(=O)O Chemical compound FC1=C(C=CC(=C1)C=1C(=NC=CC1)OC(C)C)SCCCC(=O)O VOPOFCCMXIBNSU-UHFFFAOYSA-N 0.000 claims 1
- BRRPDCHQPZFRKQ-UHFFFAOYSA-N FC1=C(OC(CCC(=O)O)C)C(=CC(=C1)C1=CC(=CC=C1)OC1=CC=CC=C1)F Chemical compound FC1=C(OC(CCC(=O)O)C)C(=CC(=C1)C1=CC(=CC=C1)OC1=CC=CC=C1)F BRRPDCHQPZFRKQ-UHFFFAOYSA-N 0.000 claims 1
- UCKHAJKUHNWNDU-UHFFFAOYSA-N FC1=C(OCCCC(=O)O)C(=CC(=C1)C1=CC(=CC=C1)NCCC)F Chemical compound FC1=C(OCCCC(=O)O)C(=CC(=C1)C1=CC(=CC=C1)NCCC)F UCKHAJKUHNWNDU-UHFFFAOYSA-N 0.000 claims 1
- LUGGTJYLJDJEHK-UHFFFAOYSA-N FC1=C(OCCCC(=O)O)C(=CC(=C1)C1=CC(=CC=C1)OC1=CC=CC=C1)F Chemical compound FC1=C(OCCCC(=O)O)C(=CC(=C1)C1=CC(=CC=C1)OC1=CC=CC=C1)F LUGGTJYLJDJEHK-UHFFFAOYSA-N 0.000 claims 1
- CADASFOYFZKSMR-UHFFFAOYSA-N FC1=C(OCCCC(=O)O)C(=CC(=C1)C1=NC(=CC=C1)CC(C)C)F Chemical compound FC1=C(OCCCC(=O)O)C(=CC(=C1)C1=NC(=CC=C1)CC(C)C)F CADASFOYFZKSMR-UHFFFAOYSA-N 0.000 claims 1
- LLIXPYGPXLJZCP-UHFFFAOYSA-N FC1=C(OCCCC(=O)O)C(=CC(=C1)C1=NC(=CC=C1)N(C1=CC=CC=C1)C)F Chemical compound FC1=C(OCCCC(=O)O)C(=CC(=C1)C1=NC(=CC=C1)N(C1=CC=CC=C1)C)F LLIXPYGPXLJZCP-UHFFFAOYSA-N 0.000 claims 1
- MYLLLHTXCVHDAO-UHFFFAOYSA-N FC1=C(OCCCC(=O)O)C(=CC(=C1)C1=NC(=CC=C1)NC(C)C)F Chemical compound FC1=C(OCCCC(=O)O)C(=CC(=C1)C1=NC(=CC=C1)NC(C)C)F MYLLLHTXCVHDAO-UHFFFAOYSA-N 0.000 claims 1
- DVYSDSDTLDAOIE-UHFFFAOYSA-N FC1=C(OCCCC(=O)O)C(=CC(=C1)C=1C(=NC=CC1)CC(C)C)F Chemical compound FC1=C(OCCCC(=O)O)C(=CC(=C1)C=1C(=NC=CC1)CC(C)C)F DVYSDSDTLDAOIE-UHFFFAOYSA-N 0.000 claims 1
- ABBNRGGURCARHX-UHFFFAOYSA-N FC1=C(OCCCC(=O)O)C(=CC(=C1)C=1C(=NC=CC1)N1CCCC1)F Chemical compound FC1=C(OCCCC(=O)O)C(=CC(=C1)C=1C(=NC=CC1)N1CCCC1)F ABBNRGGURCARHX-UHFFFAOYSA-N 0.000 claims 1
- BUQFGOXUVMGXDT-UHFFFAOYSA-N FC1=C(OCCCC(=O)O)C(=CC(=C1)C=1C(=NC=CC1)N1CCN(CC1)C)F Chemical compound FC1=C(OCCCC(=O)O)C(=CC(=C1)C=1C(=NC=CC1)N1CCN(CC1)C)F BUQFGOXUVMGXDT-UHFFFAOYSA-N 0.000 claims 1
- VNCIOYQMCCZXDM-UHFFFAOYSA-N FC1=C(OCCCC(=O)O)C(=CC(=C1)C=1C(=NC=CC1)N1N=CC(=C1)C)F Chemical compound FC1=C(OCCCC(=O)O)C(=CC(=C1)C=1C(=NC=CC1)N1N=CC(=C1)C)F VNCIOYQMCCZXDM-UHFFFAOYSA-N 0.000 claims 1
- GGAAUOLWUVUZKW-UHFFFAOYSA-N FC1=C(OCCCC(=O)O)C(=CC(=C1)C=1C(=NC=CC1)NCC1CCOCC1)F Chemical compound FC1=C(OCCCC(=O)O)C(=CC(=C1)C=1C(=NC=CC1)NCC1CCOCC1)F GGAAUOLWUVUZKW-UHFFFAOYSA-N 0.000 claims 1
- UUIPLSGTNANJOR-UHFFFAOYSA-N FC1=C(OCCCC(=O)O)C(=CC(=C1)C=1C(=NC=CC1)OC)F Chemical compound FC1=C(OCCCC(=O)O)C(=CC(=C1)C=1C(=NC=CC1)OC)F UUIPLSGTNANJOR-UHFFFAOYSA-N 0.000 claims 1
- ZFZFVVITHXVLCP-UHFFFAOYSA-N FC1=C(OCCCC(=O)O)C(=CC(=C1)C=1C(=NC=CC1)OC1=NOC(=C1)C)F Chemical compound FC1=C(OCCCC(=O)O)C(=CC(=C1)C=1C(=NC=CC1)OC1=NOC(=C1)C)F ZFZFVVITHXVLCP-UHFFFAOYSA-N 0.000 claims 1
- KFSOKMGCEDDKEI-UHFFFAOYSA-N FC1=C(OCCCC(=O)O)C(=CC(=C1)C=1C(=NC=CC1)OC1CC(CC1)O)F Chemical compound FC1=C(OCCCC(=O)O)C(=CC(=C1)C=1C(=NC=CC1)OC1CC(CC1)O)F KFSOKMGCEDDKEI-UHFFFAOYSA-N 0.000 claims 1
- AXLPPNLIRCHIAV-UHFFFAOYSA-N FC1=C(OCCCC(=O)O)C(=CC(=C1)C=1C(=NC=CC1)OCC1=COC=C1)F Chemical compound FC1=C(OCCCC(=O)O)C(=CC(=C1)C=1C(=NC=CC1)OCC1=COC=C1)F AXLPPNLIRCHIAV-UHFFFAOYSA-N 0.000 claims 1
- QFEKHLMRMGXOIO-UHFFFAOYSA-N FC1=C(OCCCC(=O)O)C(=CC(=C1)C=1C(=NC=CC1)OCC1COCC1)F Chemical compound FC1=C(OCCCC(=O)O)C(=CC(=C1)C=1C(=NC=CC1)OCC1COCC1)F QFEKHLMRMGXOIO-UHFFFAOYSA-N 0.000 claims 1
- IXFOVPWYTFXOLU-UHFFFAOYSA-N FC1=C(OCCCC(=O)O)C(=CC(=C1)C=1C(=NC=CC1)OCC1OCCC1)F Chemical compound FC1=C(OCCCC(=O)O)C(=CC(=C1)C=1C(=NC=CC1)OCC1OCCC1)F IXFOVPWYTFXOLU-UHFFFAOYSA-N 0.000 claims 1
- WSMDZRYGIZESLJ-UHFFFAOYSA-N FC1=C(OCCCC(=O)O)C(=CC(=C1)C=1C(=NC=CC1)OCCOC)F Chemical compound FC1=C(OCCCC(=O)O)C(=CC(=C1)C=1C(=NC=CC1)OCCOC)F WSMDZRYGIZESLJ-UHFFFAOYSA-N 0.000 claims 1
- APUZADOJKNMBCX-UHFFFAOYSA-N FC1=C(OCCCC(=O)O)C(=CC(=C1)C=1C(=NC=CC1)SCCC)F Chemical compound FC1=C(OCCCC(=O)O)C(=CC(=C1)C=1C(=NC=CC1)SCCC)F APUZADOJKNMBCX-UHFFFAOYSA-N 0.000 claims 1
- CXSUHNWHODYORG-UHFFFAOYSA-N FC1=C(OCCCCC(=O)O)C(=CC(=C1)C=1C(=NC=CC1)OC(C)C)F Chemical compound FC1=C(OCCCCC(=O)O)C(=CC(=C1)C=1C(=NC=CC1)OC(C)C)F CXSUHNWHODYORG-UHFFFAOYSA-N 0.000 claims 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 1
- QAPXQGBQAUOWLW-UHFFFAOYSA-N N1(CC1)CCOC1=NC=CC=C1C1=CC(=C(OCCCC(=O)O)C(=C1)F)F Chemical compound N1(CC1)CCOC1=NC=CC=C1C1=CC(=C(OCCCC(=O)O)C(=C1)F)F QAPXQGBQAUOWLW-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- 210000004369 blood Anatomy 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000008103 glucose Substances 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
Classifications
-
- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4412—Non condensed pyridines; Hydrogenated derivatives thereof having oxo groups directly attached to the heterocyclic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
-
- 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
- C07C323/52—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 the carbon skeleton being acyclic and saturated
-
- 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
- C07C323/53—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 the carbon skeleton being saturated and containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/72—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings and other rings
-
- 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
-
- 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
-
- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
-
- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
-
- 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pain & Pain Management (AREA)
- Child & Adolescent Psychology (AREA)
- Gastroenterology & Hepatology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Metal-Oxide And Bipolar Metal-Oxide Semiconductor Integrated Circuits (AREA)
Claims (292)
1. Диарильные производные формулы 1 или их фармацевтически приемлемые соли или изомеры:
[Формула 1]
в которой А и В независимо представляют собой фенил или пиридин,
любой из R1-D и R2-Е не может существовать, D и Е независимо представляют собой углерод, азот, кислорода или серу, или представляют собой непосредственную связь, и любой из R1 и R2 может не существовать, или R1 и R2 независимо представляют собой водород, галоген, необязательно замещенный С1-С6-алкил, С3-С10-циклоалкил, С2-С6-алкенил, С2-С6-алкинил, С3-С10-гетероциклоалкил, С1-С6-алкил-С3-С10-циклоалкил, С1-С6-алкил-С3-С10-гетероциклоалкил, арил, С1-С6-алкиларил, гетероарил или С1-С6-алкил-С5-С6-гетероалкил, и когда D и Е представляют собой азот или углерод, R1 и R2 могут представлять собой два или три необязательно замещенных С1-С6-алкила, С3-С10-циклоалкила, С2-С6-алкенила, С2-С6-алкинила, С1-С6-алкил-С3-С10-циклоалкила, арила или С1-С6-алкиларила, которые могут быть одинаковыми или различными,
G представляет собой -J-(CR5C6)p, где J представляет собой кислород или серу, R5 и R6 независимо представляют собой водород, галоген, необязательно замещенный алкил или циклоалкил, гидроксид или амин, и R5 и R6, замещенные по одному и тому же или различным атомам углерода, могут быть связаны между собой с образованием необязательно замещенного циклоалкила или гетероциклоалкила,
R1 и R4 не могут существовать независимо друг от друга в зависимости от числа m или n, или независимо представляют собой водород, галоген или необязательно замещенный С1-С6-алкил или С1-С6-алкокси,
R7 представляет собой водород, алкил или циклоалкил,
m и n независимо представляют собой целое число от 0 до 5, а
р представляет собой целое число от 1 до 6.
2. Диарильные производные или их фармацевтически приемлемые соли или изомеры по п. 1, выбранные из следующих соединений:
4-[4-(6-фенокси-2-пиридил)фенокси]масляная кислота,
4-[2,6-дифтор-4-(6-изопропилсульфанил-2-пиридил)фенокси]масляная кислота,
4-[2,6-дифтор-4-(6-фенокси-2-пиридил)фенокси]масляная кислота,
4-[2-хлор-4-(6-изопропилсульфанил-2-пиридил)фенокси]масляная кислота,
4-[2-фтор-4-(6-изопропилсульфанил-2-пиридил)фенокси]масляная кислота,
4-[4-(6-циклопентилсульфанил-2-пиридил)-2,6-дифторфенокси]масляная кислота,
4-[4-(2-циклобутилсульфанилпиридин-3-ил)-2-метоксифенокси]масляная кислота,
4-[2,6-дифтор-4-(2-изопропилсульфанил-4-пиридил)фенокси]масляная кислота,
4-[4-[6-(циклопентокси)-2-пиридил]-2,6-дифторфенокси]масляная кислота,
4-[4-(2-циклобутилсульфанилпиридин-3-ил)-2,6-диметилфенокси]масляная кислота,
4-[4-[3-(циклопентокси)фенил]-2,6-дифторфенокси]масляная кислота,
4-[2,6-дифтор-4-(6-пирролидин-1-ил-2-пиридил)фенокси]масляная кислота,
4-[4-(2-вторбутилсульфанилпиридин-3-ил)-2,6-диметилфенокси]масляная кислота,
4-[4-[3-(циклопентокси)фенил]-2,3-дифторфенокси]масляная кислота,
4-[2,6-дифтор-4-[6-(1-пиперидил)-2-пиридил]фенокси]масляная кислота,
4-[4-(6-анилино-2-пиридил)-2,6-дифторфенокси]масляная кислота,
4-[2,6-дифтор-4-[6-(N-метиланилино)-2-пиридил]фенокси]масляная кислота,
4-[4-[6-(циклопентиламино)-2-пиридил]-2,6-дифторфенокси]масляная кислота,
4-[4-[6-(циклопропилметилсульфанил)-2-пиридил]-2,6-дифторфенокси]масляная кислота,
4-[2,6-дифтор-4-(6-пропилсульфанил-2-пиридил)фенокси]масляная кислота,
4-[2,6-дифтор-4-(6-изопропокси-2-пиридил)фенокси]масляная кислота,
4-[2,6-дифтор-4-(6-пропокси-2-пиридил)фенокси]масляная кислота,
4-[4-[6-(циклопропилметокси)-2-пиридил]-2,6-дифторфенокси]масляная кислота,
4-[4-[6-(циклобутокси)-2-пиридил]-2,6-дифторфенокси]масляная кислота,
4-[4-[6-(циклобутокси)-2-пиридил]-2-метилфенокси]масляная кислота,
4-[4-[6-(циклобутокси)-2-пиридил]-2-(трифторметил)фенокси]масляная кислота,
4-[4-(2-циклобутилсульфанил-3-пиридил)-2,6-дифторфенокси]пентановая кислота,
4-[4-[6-(циклобутокси)-2-пиридил]-2,6-дифторфенокси]пентановая кислота,
4-[[5-(2-циклобутилсульфанил-3-пиридил)-2-пиридил]окси]пентановая кислота,
4-{2,6-дифтор-4-[2-(3-метилбутилсульфанил)пиридин-3-ил]фенокси}масляная кислота,
4-{2,6-дифтор-4-[2-фторэтокси)пиридин-3-ил]фенокси}масляная кислота,
2-[1-[[4-(2-циклобутилсульфанил-3-пиридил)-2,6-дифторфенокси]метил]циклопропил]уксусная кислота,
2-[1-[[4-(3-циклобутокси)фенил]-2,6-дифторфенокси]метил]циклопропил]уксусная кислота,
4-[[6-[3-(циклобутокси)фенил]-3-пиридил]окси]масляная кислота,
4-[[6-[3-(циклопентокси)фенил]-3-пиридил]окси]масляная кислота,
4-(2'-феноксидифенил-4-илокси)масляная кислота,
4-[4-(2-изопропилсульфанилпиридин-3-ил)фенокси]масляная кислота,
4-(3,5-дифтор-2’-феноксидифенил-4-илокси)масляная кислота,
4-[4-(2-циклопентилсульфанилпиридин-3-ил)фенокси]масляная кислота,
4-[2,6-дифтор-4-(2-изопропилсульфанилпиридин-3-ил)фенокси]масляная кислота,
4-[2,6-дифтор-4-(2-феноксипиридин-3-ил)фенокси]масляная кислота,
4-[2,6-дифтор-4-(2-изопропоксипиридин-3-ил)фенокси]масляная кислота,
4-[4-(2-циклопентилоксипиридин-3-ил)-2,6-дифторфенокси]масляная кислота,
4-[4-(2-циклопентилсульфанилпиридин-3-ил)-2,6-дифторфенокси]масляная кислота,
4-[4-(2-циклопропилметоксипиридин-3-ил)-2,6-дифторфенокси]масляная кислота,
4-[4-(2-циклопропилметилсульфанилпиридин-3-ил)-2,6-дифторфенокси]масляная кислота,
4-[4-(2-циклобутилсульфанилпиридин-3-ил)фенокси]масляная кислота,
4-[4-(2-циклопропилметилсульфанилпиридин-3-ил)фенокси]масляная кислота,
4-[4-(2-циклобутилметилсульфанилпиридин-3-ил)-2,6-дифторфенокси]масляная кислота,
4-[4-(2-пропилсульфанилпиридин-3-ил)фенокси]масляная кислота,
4-(3,5-дифтор-2’-изопропоксидифенил-4-илокси)масляная кислота,
4-(2’-циклобутокси-3,5-дифтордифенил-4-илокси)масляная кислота,
4-(2’-циклопропилметокси-3,5-дифтордифенил-4-илокси)масляная кислота,
4-(2’-циклопентилокси-3,5-дифтордифенил-4-илокси)масляная кислота,
4-(2’-циклопентилоксидифенил-4-илокси)масляная кислота,
4-(2’-изопропоксидифенил-4-илокси)масляная кислота,
4-(2’-циклопропилметоксидифенил-4-илокси)масляная кислота,
4-[4-(2-циклобутилсульфанилпиридин-3-ил)-2,6-дифторфенокси]-2-метилмасляная кислота,
2-[4-(2-циклобутилсульфанилпиридин-3-ил)-2,6-дифторфеноксиметил]циклопропанкарбоновая кислота,
4-[4-(2-циклобутилсульфанилпиридин-3-ил)-2,5-дифторфенокси]масляная кислота,
4-[4-(6-циклобутилсульфанилпиридин-2-ил)-2,5-дифторфенокси]масляная кислота,
4-[4-(2-третбутилсульфанилпиридин-3-ил)-2,6-дифторфенокси]масляная кислота,
6-[2,6-дифтор-4-(2-пропилсульфанил-3-пиридил)фенокси]гексановая кислота,
4-{2,6-дифтор-4-[6-(2-метилпропенил)пиридин-2-ил]фенокси}масляная кислота,
4-[2,6-дифтор-4-(6-изобутилпиридин-2-ил)фенокси]масляная кислота,
4-[4-(2-циклобутилсульфанилпиридин-3-ил)-3,5-дифторфенокси]масляная кислота,
4-{2,6-дифтор-4-[2-(тетрагидропиран-4-илокси)пиридин-3-ил]фенокси}масляная кислота,
4-{2,6-дифтор-4-[2-(тетрагидрофуран-3-илокси)пиридин-3-ил]фенокси}масляная кислота,
4-[4-(2-циклобутоксипиридин-3-ил)-2,6-дифторфенокси]масляная кислота,
4-{2,6-дифтор-4-[2-(2-метоксиэтокси)пиридин-3-ил]фенокси}масляная кислота,
4-[2,6-дифтор-4-(2-пирролидин-1-ил-3-пиридил)фенокси]масляная кислота,
4-[4-[2-циклопентиламино)-3-пиридил]-2,6-дифтор-фенокси]масляная кислота,
4-[4-[2-(циклопропилметиламино)-3-пиридил]-2,6-дифторфенокси]масляная кислота,
4-[4-[6-(циклопропилметиламино)-2-пиридил]-2,6-дифторфенокси]масляная кислота,
4-[2,6-дифтор-4-[2-(изопропиламино)-3-пиридил] фенокси]масляная кислота,
4-[4-[2-(циклопропиламино)-3-пиридил]-2,6-дифторфенокси]масляная кислота,
4-[2,6-дифтор-4-[6-(изопропиламино)-2-пиридил]фенокси]масляная кислота,
4-[4-[2-(циклопентиламино)фенил]-2,6-дифторфенокси]масляная кислота,
4-[4-[3-(циклопентиламино)фенил]-2,6-дифторфенокси]масляная кислота,
4-[2,6-дифтор-4-[2-(пропиламино)фенил]фенокси]масляная кислота,
4-[4-[2-(циклопропилметиламино)фенил]-2,6-дифторфенокси]масляная кислота,
4-[2,6-дифтор-4-[2-(изопропиламино)фенил]фенокси]масляная кислота,
4-[4-[2-(циклопентиламино)фенил]фенокси]масляная кислота,
4-[4-[2-(циклопропилметиламино)фенил]фенокси]масляная кислота,
4-[4-[2-(пропиламино)фенил]фенокси]масляная кислота,
4-[4-[2-(изопропиламино)фенил]фенокси]масляная кислота,
4-[4-[2-(циклобутиламино)фенил]фенокси]масляная кислота,
4-[4-[2-(циклобутиламино)фенил]-2,6-дифторфенокси]масляная кислота,
4-[4-[3-(циклопропилметиламино)фенил]-2,6-дифторфенокси]масляная кислота,
4-[2,6-дифтор-4-[3-(изопропиламино)фенил]фенокси]масляная кислота,
4-[2,6-дифтор-4-(3-пирролидин-1-илфенил)фенокси]масляная кислота,
4-[4-[3-(циклобутиламино)фенил]-2,6-дифторфенокси]масляная кислота,
4-[2,6-дифтор-4-[3-(пропиламино)фенил]фенокси]масляная кислота,
4-[4-[5-хлор-2-(циклопентиламино)фенил]-2,6-дифторфенокси]масляная кислота,
4-[4-[2-(циклопентиламино)-5-фторфенил]-2,6-дифторфенокси]масляная кислота,
4-[4-[3-(циклопентилфенил]-2,6-дифторфенокси]масляная кислота,
4-[4-[2-(циклопентилметил)фенил]-2,6-дифторфенокси]масляная кислота,
4-[4-[6-(циклопентилметил)-2-пиридил]-2,6-дифторфенокси]масляная кислота,
4-[4-[2-(циклобутилметил)фенил]-2,6-дифторфенокси]масляная кислота,
4-[4-[3-(циклобутилметил)фенил]-2,6-дифторфенокси]масляная кислота,
4-[4-[6-(циклобутилметил)-2-пиридил]-2,6-дифторфенокси]масляная кислота,
4-[4-(2-циклопентилфенил)-2,6-дифторфенокси]масляная кислота,
4-[4-(6-циклопентил-2-пиридил)-2,6-дифторфенокси]масляная кислота,
4-[2,6-дифтор-4-(2-изобутил-3-пиридил)фенокси]масляная кислота,
4-[4-(2-циклопентил-3-пиридил)-2,6-дифторфенокси]масляная кислота,
4-[4-[2-(циклопентилметил)-3-пиридил]-2,6-дифторфенокси]масляная кислота,
4-[2,6-дифтор-4-(2-пиррол-1-ил-3-пиридил)фенокси]масляная кислота,
4-[2,6-дифтор-4-[2-(4-метилпиразол-1-ил)-3-пиридил]фенокси]масляная кислота,
4-[2,6-дифтор-4-(2-морфолино-3-пиридил)фенокси]масляная кислота,
4-[2,6-дифтор-4-[2-(тетрагидропиран-4-илметиламино)-3-пиридил]фенокси]масляная кислота,
4-[2,6-дифтор-4-[2-(1-пиперидил)-3-пиридил]фенокси]масляная кислота,
(4C)-4-[4-(2-циклобутилсульфанил-3-пиридил)-2,6-дифторфенокси]пентановая кислота,
(4R)-4-[4-(2-циклобутилсульфанил-3-пиридил)-2,6-дифторфенокси]пентановая кислота,
(4R)-4-[4-[3-циклобутокси)фенил]-2,6-дифторфенокси]пентановая кислота,
(4R)-4-[4-(2-циклопентилсульфанил-3-пиридил)-2,6-дифторфенокси]пентановая кислота,
4-[2,6-дифтор-4-(3-феноксифенил)фенокси]пентановая кислота,
4-(3'-циклобутоксидифенил-4-илсульфанил)масляная кислота,
4-(3'-изопропоксидифенил-4-илсульфанил)масляная кислота,
[1-(3,5-дифтор-3'-изопропоксидифенил-4-илсульфанил)циклопропил]уксусная кислота,
4-(3'-циклопентокси-3,5-дифтордифенил-4-илсульфанил)масляная кислота,
4-[4-(2-циклопентоксипиридин-3-ил)фенилсульфанил]масляная кислота,
4-[4-(2-циклопропилметоксипиридин-3-ил)фенилсульфанил]масляная кислота,
4-(3'-феноксидифенил-4-илсульфанил)масляная кислота,
4-(3'-циклопентоксидифенил-4-илсульфанил)масляная кислота,
4-(3'-пропоксидифенил-4-илсульфанил)масляная кислота,
4-[4-(6-циклобутоксипиридин-2-ил)фенилсульфанил]масляная кислота,
4-[4-(6-циклопентоксипиридин-2-ил)фенилсульфанил]масляная кислота,
4-[4-(6-изопропоксипиридин-2-ил)фенилсульфанил]масляная кислота,
4-[4-(2-изопропоксипиридин-3-ил)фенилсульфанил]масляная кислота,
4-[4-(6-пропоксипиридин-2-ил)фенилсульфанил]масляная кислота,
4-[4-(6-циклопентилсульфанилпиридин-2-ил)фенилсульфанил]масляная кислота,
4-(3'-циклобутокси-3,5-дифтордифенил-4-илсульфанил)масляная кислота,
4-(3,5-дифтор-3'-изопропоксидифенил-4-илсульфанил)масляная кислота,
4-[2,6-дифтор-4-(6-пропоксипиридин-2-ил)фенилсульфанил]масляная кислота,
4-[2,6-дифтор-4-(6-изопропоксипиридин-2-ил)фенилсульфанил]масляная кислота,
4-[2,6-дифтор-4-(2-изопропоксипиридин-3-ил)фенилсульфанил]масляная кислота,
4-[2,6-дифтор-4-(2-пропоксипиридин-3-ил)фенилсульфанил]масляная кислота,
4-[2,6-дифтор-4-(6-изопропилсульфанил-пиридин-2-ил)фенилсульфанил]масляная кислота,
4-[2,6-дифтор-4-(6-пропилсульфанил-пиридин-2-ил)фенилсульфанил]масляная кислота,
4-[4-(2-циклобутилсульфанил-пиридин-3-ил)-2,6-дифторфенилсульфанил]масляная кислота,
4-[4-(2-циклобутоксипиридин-3-ил)фенилсульфанил]масляная кислота,
4-[4-(2-циклобутоксипиридин-3-ил)-2,6-дифторфенилсульфанил]масляная кислота,
4-[4-(2-циклопентоксипиридин-3-ил)-2,6-дифторфенилсульфанил]масляная кислота,
4-[2,6-дифтор-4-(2-изопропилсульфанилпиридин-3-ил)фенилсульфанил]масляная кислота,
4-[4-(2-циклопентилсульфанилпиридин-3-ил)-2,6-дифторфенилсульфанил]масляная кислота,
4-[4-(2-изопропилсульфанилпиридин-3-ил)фенилсульфанил]масляная кислота,
4-[4-(2-циклопентилсульфанилпиридин-3-ил)фенилсульфанил]масляная кислота,
4-[2-фтор-4-(6-изопропоксипиридин-2-ил)фенилсульфанил]масляная кислота,
4-[4-(2-циклопентоксипиридин-3-ил)-2-фторфенилсульфанил]масляная кислота,
4-[4-(2-циклобутилсульфанилпиридин-3-ил)-2-фторфенилсульфанил]масляная кислота,
4-[4-(2-циклобутилсульфанилпиридин-3-ил)фенилсульфанил]масляная кислота,
4-[4-(6-циклобутоксипиридин-2-ил)-2,6-дифторфенилсульфанил]масляная кислота,
4-[4-(6-циклопентоксипиридин-2-ил)-2,6-дифторфенилсульфанил]масляная кислота,
4-[4-(6-циклобутилсульфанилпиридин-2-ил)фенилсульфанил]масляная кислота,
4-[4-(6-циклопропилметоксипиридин-2-ил)-2,6-дифторфенилсульфанил]масляная кислота,
4-[4-(6-циклобутилсульфанилпиридин-2-ил)-2,6-дифторфенилсульфанил]масляная кислота,
4-[4-(6-циклопентилсульфанилпиридин-2-ил)-2,6-дифторфенилсульфанил]масляная кислота,
4-(2'-циклопентиламино-3-фтордифенил-4-илсульфанил)масляная кислота,
4-(2'-циклопентиламино-3,5-дифтордифенил-4-илсульфанил)масляная кислота,
4-[2’-(циклопропилметиламино)-3,5-дифтордифенил-4-илсульфанил]масляная кислота,
4-[2-фтор-4-(2-изопропилсульфанилпиридин-3-ил)фенилсульфанил]масляная кислота,
4-[4-(2-циклопентилсульфанилпиридин-3-ил)-2-фторфенилсульфанил]масляная кислота,
4-(3,5-дифтор-2'-изопропиламинодифенил-4-илсульфанил)масляная кислота,
4-(3,5-дифтор-2'-пропиламинодифенил-4-илсульфанил)масляная кислота,
4-[4-(2-циклопропилметоксипиридин-3-ил)-2,6-дифторфенилсульфанил]масляная кислота,
4-[2,6-дифтор-4-(2-пропилсульфанилпиридин-3-ил)фенилсульфанил]масляная кислота,
4-[4-(6-циклобутилсульфанилпиридин-2-ил)-2-фторфенилсульфанил]масляная кислота,
4-[4-(2-циклопентиламинопиридин-3-ил)-2-фторфенилсульфанил]масляная кислота,
4-[2-фтор-4-(2-изопропоксипиридин-3-ил)фенилсульфанил]масляная кислота,
4-[4-(2-циклобутоксипиридин-3-ил)-2-фторфенилсульфанил]масляная кислота,
4-[2-фтор-4-(2-пирролидин-1-илпиридин-3-ил)фенилсульфанил]масляная кислота,
4-[2-фтор-4-(2-изопропиламинопиридин-3-ил)фенилсульфанил]масляная кислота,
4-(2’-циклопентиламино-3,5’-дифтордифенил-4-илсульфанил)масляная кислота,
4-(2’-циклопентиламино-5’-фтордифенил-4-илсульфанил)масляная кислота,
4-(2’-циклопентокси-5’-метилдифенил-4-илсульфанил)масляная кислота,
4-(2’-циклопентокси-4’-метоксидифенил-4-илсульфанил)масляная кислота,
масляную кислоту4-(2’-циклопентокси-5’-фтордифенил-4-илсульфанил)масляная кислота,
4-(2’-циклопентокси-3,5’-дифтордифенил-4-илсульфанил)масляная кислота,
4-[4-(2-циклопентокси-5-метилпиридин-3-ил)фенилсульфанил]масляная кислота,
4-(2’-циклопентокси-3,5,5’-трифтордифенил-4-илсульфанил)масляная кислота,
4-(2’-циклопентокси-3-фтор-4’-метоксидифенил-4-илсульфанил)масляная кислота,
4-(2’-циклопентокси-3,5-дифтор-4’-метоксидифенил-4-илсульфанил)масляная кислота,
4-(3-фтор-2’-изопропокси-4’-метоксидифенил-4-илсульфанил)масляная кислота,
4-[4-(2-циклопентокси-5-метилпиридин-3-ил)-2-фторфенилсульфанил]масляная кислота,
4-[2-фтор-4-(2-изопропокси-5-метилпиридин-3-ил)фенилсульфанил]масляная кислота,
4-(3,5'-дифтор-2'-изопропоксидифенил-4-илсульфанил)масляная кислота,
4-[4-(2-циклопентокси-6-метилпиридин-3-ил)-2-фторфенилсульфанил]масляная кислота,
4-(3,3'-дифтор-2’-изопропокси-5'-метилдифенил-4-илсульфанил)масляная кислота,
4-(3,3'-дифтор-5'-метил-2’-пропоксидифенил-4-илсульфанил)масляная кислота,
4-(3-фтор-2',4'-дипропоксидифенил-4-илсульфанил)масляная кислота,
4-(6'-циклопентокси-3,2'-дифтор-3'-метилдифенил-4-илсульфанил)масляная кислота,
4-(2'-циклопентокси-3,3'-дифтордифенил-4-илсульфанил)масляная кислота,
4-(2'-циклопентокси-3,3'-дифтордифенил-5'-метилдифенил-4-илсульфанил)масляная кислота,
5-[4-(2-циклобутилметоксипиридин-3-ил)-2,6-дифторфенокси]пентановая кислота,
5-[4-(2-циклопропоксипиридин-3-ил)-2,6-дифторфенокси]пентановая кислота,
4-[4-(2-циклопентокси-5-метилпиридин-3-ил)-2,6-дифторфенилсульфанил]масляная кислота,
4-[4-(2-циклопентоксипиридин-3-ил)фенилсульфанил]пентановая кислота,
4-[4-(2-изопропоксипиридин-3-ил)фенилсульфанил]пентановая кислота,
4-[4-(2-циклопентоксипиридин-3-ил)-2,6-дифторфенилсульфанил]пентановая кислота,
4-[4-(2-циклопентилсульфанилпиридин-3-ил)-2,6-дифторфенилсульфанил]пентановая кислота,
4-[4-[2-(2-диметиламиноэтокси)-3-пиридил]-2,6-дифторфенокси]масляная кислота,
4-[2,6-дифтор-4-(2-пропилсульфанилпиридин-3-ил)фенокси]масляная кислота,
4-[4-(2-циклопропилсульфанилпиридин-3-ил)-2,6-дифторфенокси]масляная кислота,
4-[4-(2-этинилсульфанилпиридин-3-ил)-2,6-дифторфенокси]масляная кислота,
4-[4-(2-бутилсульфанилпиридин-3-ил)-2,6-дифторфенокси]масляная кислота,
4-(2'-циклопентиламинодифенил-4-илсульфанил)масляная кислота,
4-[4-(2-циклопентокси-5-метилпиридин-3-ил)-2,6-дифторфенокси]масляная кислота,
4-[4-(6-изопропилсульфанил-2-пиридил)фенокси]масляная кислота,
4-[2,6-дифтор-4-(3-феноксифенил)фенокси]масляная кислота,
4-[4-[6-[3-(диметиламино)пирролидин-1-ил]2-пиридил]-2,6-дифторфенокси]масляная кислота,
5-[2,6-дифтор-4-(2-изопропоксипиридин-3-ил)фенокси]пентановая кислота,
5-[4-(2-циклобутоксипиридин-3-ил)-2,6-дифторфенокси]масляная кислота,
4-[2,6-дифтор-4-[2-(4-метилпиперазин-1-ил)-3-пиридил]фенокси]масляная кислота,
4-[2,6-дифтор-4-[2-(5-метилизоксазол-3-ил)окси-3-пиридил]фенокси]масляная кислота,
4-[4-[2-[2-(азиридин-1-ил)этокси]3-пиридил]-2,6-дифторфенокси]масляная кислота,
4-[2,6-дифтор-4-[2-(3-фурилметокси)-3-пиридил]фенокси]масляная кислота,
4-[2,6-дифтор-4-[2-(2-фурилметокси)-3-пиридил]фенокси]масляная кислота,
4-[2,6-дифтор-4-[2-(3-метилоксетан-3-ил)метокси]-3-пиридил]фенокси]масляная кислота,
4-[2,6-дифтор-4-[2-(тетрагидрофуран-3-илметокси)-3-пиридил]фенокси]масляная кислота,
4-[2,6-дифтор-4-[2-(тетрагидрофуран-2-илметокси)-3-пиридил]фенокси]масляная кислота,
4-[4-[2-циклобутилметоксипиридин-3-ил)-2,6-дифторфенокси]масляная кислота,
4-[4-[2-циклопропоксипиридин-3-ил)-2,6-дифторфенокси]масляная кислота,
4-[4-{2-[3-третбутилдиметилсиланокси)циклопентокси]пиридин-3-ил}-2,6-дифторфенокси]масляная кислота,
4-{2,6-дифтор-4-[2-(3-гидроксициклопентокси)пиридин-3-ил]фенокси}масляная кислота,
4-[4-[2-циклогексилоксипиридин-3-ил)-2,6-дифторфенокси]масляная кислота,
4-[4-[2-циклопентилметоксипиридин-3-ил)-2,6-дифторфенокси]масляная кислота,
4-[2,6-дифтор-4-(2-изобутоксипиридин-3-ил)фенокси]масляная кислота,
4-{4-[2-(2,2-диметилпропокси)пиридин-3-ил]-2,6-дифторфенокси}масляная кислота,
5-[4-(2-циклопентоксипиридин-3-ил)-2,6-дифторфенокси]масляная кислота,
5-[4-(2-циклобутилсульфанил-3-пиридил)-2,6-дифторфенокси]пентановая кислота,
5-[4-(2-циклопентилсульфанил-3-пиридил)-2,6-дифторфенокси]пентановая кислота,
5-[2,6-дифтор-4-(2-изопропилсульфанил-3-пиридил)фенокси]пентановая кислота,
5-[2,6-дифтор-4-(2-пропилсульфанил-3-пиридил)фенокси]пентановая кислота,
5-[2,6-дифтор-4-(6-изопропилсульфанил-2-пиридил)фенокси]пентановая кислота,
5-[2,6-дифтор-4-(6-изопропокси-2-пиридил)фенокси]пентановая кислота,
5-[4-(2-циклопропилметокси-3-пиридил)-2,6-дифторфенокси]пентановая кислота,
5-[2,6-дифтор-4-(2-тетрагидрофуран-3-илокси-3-пиридил)фенокси]пентановая кислота,
5-[2,6-дифтор-4-(2-тетрагидропиран-4-илокси-3-пиридил)фенокси]пентановая кислота,
4-[2,6-дифтор-4-(2-изопропоксипиридин-3-ил)фенилсульфанил]пентановая кислота,
5-[4-(2-циклопентилсульфанилпиридин-3-ил)фенилсульфанил]пентановая кислота,
4-{2-фтор-4-[2-(тетрагидропиран-4-илокси)пиридин-3-ил]фенилсульфанил}масляная кислота,
4-{2-фтор-4-[2-(тетрагидрофуран-3-илокси)пиридин-3-ил]фенилсульфанил}масляная кислота,
4-[4-(2-циклобутилметоксипиридин-3-ил)-2-фторфенилсульфанил]масляная кислота,
4-{2,6-дифтор-4-[2-(2,2,2-трифторэтокси)пиридин-3-ил]фенилсульфанил}масляная кислота,
4-[4-(2-циклобутилметоксипиридин-3-ил)-2,6-дифторфенилсульфанил]масляная кислота,
4-[4-(2-циклопентиламинопиридин-3-ил)-2,6-дифторфенилсульфанил]масляная кислота,
4-[2,6-дифтор-4-(2-изопропиламинопиридин-3-ил)фенилсульфанил]масляная кислота,
4-[4-(2-циклопропилметиламино)пиридин-3-ил]-2,6-дифторфенилсульфанил]масляная кислота,
5-[4-(2-циклопентоксипиридин-3-ил)-2,6-дифторфенилсульфанил]пентановая кислота,
5-[2,6-дифтор-4-(2-изопропоксипиридин-3-ил)фенилсульфанил]пентановая кислота,
5-[4-(2-циклопентоксипиридин-3-ил)фенилсульфанил]пентановая кислота,
5-[4-(2-изопропоксипиридин-3-ил)фенилсульфанил]пентановая кислота,
5-[4-(2-циклопентилсульфанилпиридин-3-ил)-2,6-дифторфенилсульфанил]пентановая кислота,
5-[2,6-дифтор-4-(2-пропилсульфанилпиридин-3-ил)фенилсульфанил]пентановая кислота,
5-[4-(2-циклопентилсульфанилпиридин-3-ил)фенилсульфанил]пентановая кислота,
5-[4-(2-циклобутилсульфанилпиридин-3-ил)фенилсульфанил]пентановая кислота,
5-[4-(2-циклобутилметоксипиридин-3-ил)-2,6-дифторфенилсульфанил]пентановая кислота,
5-[4-(2-циклобутоксипиридин-3-ил)-2,6-дифторфенилсульфанил]пентановая кислота,
6-[4-(2-циклопентилоксипиридин-3-ил)-2,6-дифторфенокси]гексановая кислота,
7-[4-(2-циклопентилоксипиридин-3-ил)-2,6-дифторфенокси]гептановая кислота,
5-[2-фтор-4-(2-изопропоксипиридин-3-ил)фенокси]пентановая кислота,
5-[4-(2-циклопентилсульфанилпиридин-3-ил)-2-фторфенокси]пентановая кислота,
5-[4-(2-циклобутилсульфанилпиридин-3-ил)-2-фторфенокси] пентановая кислота,
5-[4-(2-циклопентоксипиридин-3-ил)-2-фторфенокси] пентановая кислота,
4-[2,6-дифтор-4-(2-метоксипиридин-3-ил)фенокси]масляная кислота,
4-[4-(2-аллилоксипиридин-3-ил)-2,6-дифторфенокси]масляная кислота,
4-[4-(2-бут-2-инилоксипиридин-3-ил)-2,6-дифторфенокси]масляная кислота,
6-[4-(2-циклобутокси-3-пиридил)-2,6-дифторфенокси]гексановая кислота,
6-[4-[2-циклобутилметокси)-3-пиридил]-2,6-дифторфенокси]гексановая кислота,
6-[4-[2-циклопропилметокси)-3-пиридил]-2,6-дифторфенокси]гексановая кислота,
6-[4-(2-циклобутилсульфанил-3-пиридил)-2,6-дифторфенокси]гексановая кислота,
6-[4-(2-циклопентилсульфанил-3-пиридил)-2,6-дифторфенокси]гексановая кислота,
6-[4-(2-циклопентоксипиридин-3-ил)-2,6-дифторфенилсульфанил]гексановая кислота,
6-[4-(2-циклопентилсульфанилпиридин-3-ил)-2,6-дифторфенилсульфанил]гексановая кислота,
6-[4-(2-циклобутилсульфанилпиридин-3-ил)-2,6-дифторфенилсульфанил]гексановая кислота,
и
6-[2,6-дифтор-4-(2-пропилсульфанилпиридин-3-ил)фенилсульфанил]гексановая кислота.
3. Фармацевтическая композиция в качестве агонистов GPR120, содержащая диарильные производные, их фармацевтически приемлемые соли или изомеры по п. 1, и фармацевтически приемлемый носитель.
4. Фармацевтическая композиция для предупреждения или лечения диабета, осложнений диабета, ожирения, неалкогольного жирового гепатоза, стеатогепатита, остеопороза или воспаления, содержащая диарильные производные, их фармацевтически приемлемые соли или изомеры по п. 1, и фармацевтически приемлемый носитель.
5. Композиция для снижения уровня глюкозы в крови, содержащая диарильные производные, их фармацевтически приемлемые соли или изомеры по п. 1, и фармацевтически приемлемый носитель.
6. Способ получения композиции для предупреждения или лечения диабета, осложнений диабета, ожирения, неалкогольного жирового гепатоза, стеатогепатита, остеопороза или воспаления, включающий в себя стадию смешивания диарильных производных, их фармацевтически приемлемых солей или изомеров по п. 1 с фармацевтически приемлемым носителем.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20130074927 | 2013-06-27 | ||
| KR10-2013-0074927 | 2013-06-27 | ||
| PCT/KR2014/005688 WO2014209034A1 (en) | 2013-06-27 | 2014-06-26 | Biaryl derivatives as gpr120 agonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2016102313A true RU2016102313A (ru) | 2017-08-01 |
| RU2641003C2 RU2641003C2 (ru) | 2018-01-15 |
Family
ID=52142283
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2016102313A RU2641003C2 (ru) | 2013-06-27 | 2014-06-26 | Биарильные производные в качестве агонистов gpr120 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US10221138B2 (ru) |
| EP (2) | EP3013796B9 (ru) |
| JP (1) | JP6322704B2 (ru) |
| KR (1) | KR101662217B1 (ru) |
| CN (1) | CN105392777B (ru) |
| AU (2) | AU2014299457B2 (ru) |
| BR (1) | BR112015032370B1 (ru) |
| CA (1) | CA2912747C (ru) |
| CY (1) | CY1122742T1 (ru) |
| DK (1) | DK3013796T3 (ru) |
| ES (1) | ES2784489T3 (ru) |
| HR (1) | HRP20200386T1 (ru) |
| HU (1) | HUE049425T2 (ru) |
| LT (1) | LT3013796T (ru) |
| MX (1) | MX378007B (ru) |
| PL (1) | PL3013796T3 (ru) |
| PT (1) | PT3013796T (ru) |
| RS (1) | RS60128B9 (ru) |
| RU (1) | RU2641003C2 (ru) |
| SI (1) | SI3013796T1 (ru) |
| WO (1) | WO2014209034A1 (ru) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101942752B1 (ko) * | 2012-11-05 | 2019-01-28 | 주식회사 엘지화학 | Gpr120 효능제로서의 티오아릴 유도체 |
| CN115925679A (zh) | 2014-12-24 | 2023-04-07 | 株式会社Lg化学 | 作为gpr120激动剂的联芳基衍生物 |
| EP3253745B1 (en) * | 2015-02-05 | 2021-09-29 | Piramal Enterprises Limited | Compounds containing carbon-carbon linker as gpr120 agonists |
| EP3281937A1 (en) | 2016-08-09 | 2018-02-14 | Dompé farmaceutici S.p.A. | Sulfonamides as gpr40- and gpr120-agonists |
| EP3509588B1 (en) | 2016-09-12 | 2023-06-07 | Integral Health,Inc. | Bicyclic compounds useful as gpr120 modulators |
| WO2018049324A1 (en) | 2016-09-12 | 2018-03-15 | Numerate, Inc. | Monocyclic compounds useful as gpr120 modulators |
| AU2018287777B2 (en) * | 2017-06-20 | 2020-05-21 | Shandong Danhong Pharmaceutical Co., Ltd. | SSAO inhibitor |
| CN112074505B (zh) | 2018-03-08 | 2024-04-05 | 因赛特公司 | 作为PI3K-γ抑制剂的氨基吡嗪二醇化合物 |
| EP3765446A1 (en) | 2018-03-15 | 2021-01-20 | AXXAM S.p.A. | Substituted pyrazoles ffa4/gpr120 receptor agonists |
| US11046658B2 (en) | 2018-07-02 | 2021-06-29 | Incyte Corporation | Aminopyrazine derivatives as PI3K-γ inhibitors |
| KR102275536B1 (ko) | 2021-02-16 | 2021-07-09 | 주식회사 듀오백 | 의자 좌판의 레그 서포터 구조 |
| AR128613A1 (es) | 2022-02-25 | 2024-05-29 | Lhotse Bio Inc | Compuestos y composiciones para el tratamiento de afecciones asociadas con la actividad del receptor de lpa |
Family Cites Families (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE586247A (ru) * | 1959-01-07 | |||
| US4181729A (en) * | 1979-03-21 | 1980-01-01 | Pfizer Inc. | Phenyl or phenoxy substituted spiro-imidazolidinedione derivatives |
| IT1211135B (it) * | 1981-11-24 | 1989-09-29 | Ausonia Farma Srl | Composti ad attivita'analgesica e antiinfiammatoria, processo per la loro preparazione e relative composizioni farmaceutiche. |
| JPH01128958A (ja) * | 1987-11-13 | 1989-05-22 | Chisso Corp | α−アリールオキシプロピオン酸エステル類 |
| US5145790A (en) * | 1990-05-04 | 1992-09-08 | Abbott Laboratories | Reagents and method for detecting polychlorinated biphenyls |
| FR2665159B1 (fr) * | 1990-07-24 | 1992-11-13 | Rhone Poulenc Sante | Nouveaux derives de la pyridine et de la quinoleine, leur preparation et les compositions pharmaceutiques qui les contiennent. |
| DE4323916A1 (de) * | 1993-07-16 | 1995-01-19 | Basf Ag | Substituierte 2-Phenylpyridine |
| US5665777A (en) | 1995-11-14 | 1997-09-09 | Abbott Laboratories | Biphenyl hydroxamate inhibitors of matrix metalloproteinases |
| US6566384B1 (en) | 1996-08-07 | 2003-05-20 | Darwin Discovery Ltd. | Hydroxamic and carboxylic acid derivatives having MMP and TNF inhibitory activity |
| US6300514B1 (en) | 1997-06-25 | 2001-10-09 | Ono Pharmaceutical Co., Ltd. | Aryl (sulfide, sulfoxide and sulfone) derivatives and drugs containing the same as the active ingredient |
| HUP0100812A3 (en) | 1997-11-21 | 2002-11-28 | Upjohn Co | Alpha-hydroxy, -amino and -fluoro derivatives of betha-sulphonyl hydroxamic acids as matrix metalloproteinases inhibitors |
| US6232322B1 (en) | 1998-05-12 | 2001-05-15 | American Home Products Corporation | Biphenyl oxo-acetic acids useful in the treatment of insulin resistance and hyperglycemia |
| JP2002514635A (ja) | 1998-05-12 | 2002-05-21 | アメリカン・ホーム・プロダクツ・コーポレイション | インスリン耐性および高血糖の処置に有用なビフェニルオキソ−酢酸 |
| US6699896B1 (en) | 1998-05-12 | 2004-03-02 | Wyeth | Oxazole-aryl-carboxylic acids useful in the treatment of insulin resistance and hyperglycemia |
| FR2780402B1 (fr) * | 1998-06-30 | 2001-04-27 | Adir | Nouveaux composes acides carboxyliques et hydroxamiques inhibiteurs de metalloproteases, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2791982B1 (fr) * | 1999-04-06 | 2002-12-27 | Inst Nat Sante Rech Med | Inhibiteurs de lta4 hydrolase et leurs applications therapeutiques. |
| MXPA03001136A (es) * | 2000-08-11 | 2003-06-24 | Eisai Co Ltd | Compuesto de 2-aminopiridina y uso medico del mismo. |
| JP2002128731A (ja) * | 2000-10-25 | 2002-05-09 | Fujirebio Inc | フェノキシ化合物 |
| JP2002175617A (ja) * | 2000-12-06 | 2002-06-21 | Sony Corp | 磁気記録媒体 |
| CA2436535A1 (en) * | 2001-01-31 | 2002-08-08 | Prizer Products Inc. | Nicotinamide biaryl derivatives useful as inhibitors of pde4 isozymes |
| US7109354B2 (en) * | 2002-05-28 | 2006-09-19 | 3-Dimensional Pharmaceuticals, Inc. | Thiophene amidines, compositions thereof, and methods of treating complement-mediated diseases and conditions |
| WO2004000814A1 (en) * | 2002-06-25 | 2003-12-31 | Merck Frosst Canada & Co. | 8-(biaryl) quinoline pde4 inhibitors |
| WO2004010996A1 (ja) * | 2002-07-29 | 2004-02-05 | Shizuoka Coffein Co., Ltd. | 1,3アゾール誘導体及び同誘導体を含む血栓症治療のための医薬組成物 |
| DE10250743A1 (de) * | 2002-10-31 | 2004-05-19 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Amid-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
| WO2004072016A1 (ja) | 2003-02-14 | 2004-08-26 | Kissei Pharmaceutical Co., Ltd. | アミノアルコール誘導体、それを含有する医薬組成物およびそれらの用途 |
| SE0301010D0 (sv) * | 2003-04-07 | 2003-04-07 | Astrazeneca Ab | Novel compounds |
| EA200501713A1 (ru) * | 2003-04-30 | 2006-06-30 | ДЗЕ ИНСТИТЬЮТС ФОР ФАРМАСЬЮТИКАЛ ДИСКАВЕРИ, ЭлЭлСи | Фенилзамещённые карбоновые кислоты |
| ITRM20030305A1 (it) | 2003-06-20 | 2004-12-21 | Sigma Tau Ind Farmaceuti | Preparazione di nuovi derivati di acidi fenil o fenossialchil mono e dicarbossilici utili nel trattamento dell'iperglicemia e dell'ipertrigliceridemia tipiche del diabete del tipo ii. |
| WO2005051373A1 (ja) * | 2003-11-26 | 2005-06-09 | Takeda Pharmaceutical Company Limited | 受容体機能調節剤 |
| JP2005247822A (ja) * | 2004-02-04 | 2005-09-15 | Horiba Biotechnology Co Ltd | コプラナーpcbハプテン、コプラナーpcbに対する抗体およびそれを用いる免疫学的測定方法 |
| CN1922151A (zh) | 2004-02-12 | 2007-02-28 | 特兰斯泰克制药公司 | 取代的吡咯衍生物、组合物和使用方法 |
| FR2869611B1 (fr) * | 2004-05-03 | 2006-07-28 | Merck Sante Soc Par Actions Si | Derives de l'acide hexenoique, procedes pour leur preparation, compositions pharmaceutiques les contenant et applications en therapeutique |
| ES2564167T3 (es) * | 2004-07-08 | 2016-03-18 | Novo Nordisk A/S | Conjugados de polipéptidos de acción prolongada que contienen una fracción tetrazol |
| GB0422057D0 (en) | 2004-10-05 | 2004-11-03 | Astrazeneca Ab | Novel compounds |
| US20090130344A1 (en) * | 2005-11-10 | 2009-05-21 | Masaki Okazaki | Composition, film and liquid crystal display |
| CA2656564C (en) * | 2006-06-29 | 2015-06-16 | Kinex Pharmaceuticals, Llc | Biaryl compositions and methods for modulating a kinase cascade |
| DK2041071T3 (da) | 2006-06-29 | 2014-09-01 | Kinex Pharmaceuticals Llc | Biarylsammensætninger og fremgangsmåder til modulering af en kinasekaskade |
| FR2903984B1 (fr) | 2006-07-24 | 2008-10-03 | Genfit Sa | Derives d'imidazolones substitues, preparation et utilisations |
| AU2007299261A1 (en) | 2006-09-21 | 2008-03-27 | Novartis Ag | Pyrrole derivatives useful for the treatment of cytokine-mediated diseases |
| WO2008066131A1 (en) | 2006-12-01 | 2008-06-05 | Banyu Pharmaceutical Co., Ltd. | Novel phenyl-isoxazol-3-ol derivative |
| BRPI0807637A2 (pt) * | 2007-02-22 | 2014-06-03 | Irm Llc | Derivados de tiazol como moduladores de receptores acoplados à proteína g |
| US20100274022A1 (en) | 2007-04-26 | 2010-10-28 | Pharmafrontier Co., Ltd. | G protein-coupled receptor inhibitor and pharmaceutical product |
| WO2008139987A1 (ja) * | 2007-04-26 | 2008-11-20 | Japan Science And Technology Agency | Gタンパク質共役型レセプタ-作動剤 |
| WO2009011285A1 (ja) * | 2007-07-13 | 2009-01-22 | Taisho Pharmaceutical Co., Ltd. | ヘテロアリールベンゼン化合物 |
| WO2009151800A1 (en) * | 2008-05-07 | 2009-12-17 | Merck & Co., Inc. | Soluble epoxide hydrolase inhibitors, compositions containing such compounds and methods of treatment |
| CA2725316A1 (en) | 2008-06-02 | 2009-12-10 | Banyu Pharmaceutical Co., Ltd. | Novel isoxazole derivative |
| AU2009254547A1 (en) * | 2008-06-04 | 2009-12-10 | Astrazeneca Ab (Publ) | New compounds V |
| KR20100022592A (ko) * | 2008-08-20 | 2010-03-03 | 주식회사 코리아티슈뱅크 | 골형성단백질이 코팅된 골이식재 |
| WO2010048149A2 (en) * | 2008-10-20 | 2010-04-29 | Kalypsys, Inc. | Heterocyclic modulators of gpr119 for treatment of disease |
| WO2010048207A2 (en) | 2008-10-21 | 2010-04-29 | Metabolex, Inc. | Aryl gpr120 receptor agonists and uses thereof |
| AR074760A1 (es) | 2008-12-18 | 2011-02-09 | Metabolex Inc | Agonistas del receptor gpr120 y usos de los mismos en medicamentos para el tratamiento de diabetes y el sindrome metabolico. |
| AU2010221980A1 (en) * | 2009-03-11 | 2011-10-13 | Msd K.K. | Novel isoindolin-1-one derivative |
| JP5730190B2 (ja) | 2009-03-31 | 2015-06-03 | 株式会社レナサイエンス | プラスミノーゲンアクチベーターインヒビター−1阻害剤 |
| US20120035196A1 (en) | 2009-04-22 | 2012-02-09 | Kenji Negoro | Carboxylic acid compound |
| US8586776B2 (en) * | 2009-11-05 | 2013-11-19 | Fibrostatin, S.L. | GPBP inhibition using Q2 peptidomimetics |
| CA2801182A1 (en) * | 2010-06-16 | 2011-12-22 | Metabolex, Inc. | Gpr120 receptor agonists and uses thereof |
| AR081930A1 (es) | 2010-06-16 | 2012-10-31 | Ardea Biosciences Inc | Compuestos de tioacetato |
| EA201390404A1 (ru) * | 2010-09-24 | 2013-09-30 | Ранбакси Лабораториз Лимитед | Ингибиторы матричной металлопротеиназы |
| PH12013501268A1 (en) | 2010-12-17 | 2016-04-01 | Mitsubishi Tanabe Pharma Corp | Continuous arycyclic compound |
| WO2012120415A1 (en) * | 2011-03-04 | 2012-09-13 | Novartis Ag | Tetrasubstituted cyclohexyl compounds as kinase inhibitors |
| WO2013056679A1 (en) | 2011-10-21 | 2013-04-25 | Beijing Hanmi Pharmaceutical Co., Ltd | Novel heteroaryl-amino derivatives |
| US9546155B2 (en) * | 2012-06-15 | 2017-01-17 | Mitsubishi Tanabe Pharma Corporation | Aromatic heterocyclic compound |
-
2014
- 2014-06-26 BR BR112015032370-7A patent/BR112015032370B1/pt active IP Right Grant
- 2014-06-26 DK DK14818620.8T patent/DK3013796T3/da active
- 2014-06-26 US US14/894,928 patent/US10221138B2/en active Active
- 2014-06-26 WO PCT/KR2014/005688 patent/WO2014209034A1/en not_active Ceased
- 2014-06-26 EP EP14818620.8A patent/EP3013796B9/en active Active
- 2014-06-26 CA CA2912747A patent/CA2912747C/en active Active
- 2014-06-26 HU HUE14818620A patent/HUE049425T2/hu unknown
- 2014-06-26 KR KR1020140078807A patent/KR101662217B1/ko active Active
- 2014-06-26 HR HRP20200386TT patent/HRP20200386T1/hr unknown
- 2014-06-26 CN CN201480036409.7A patent/CN105392777B/zh active Active
- 2014-06-26 PT PT148186208T patent/PT3013796T/pt unknown
- 2014-06-26 JP JP2016523650A patent/JP6322704B2/ja active Active
- 2014-06-26 RS RS20200286A patent/RS60128B9/sr unknown
- 2014-06-26 RU RU2016102313A patent/RU2641003C2/ru active
- 2014-06-26 SI SI201431518T patent/SI3013796T1/sl unknown
- 2014-06-26 AU AU2014299457A patent/AU2014299457B2/en active Active
- 2014-06-26 MX MX2015016543A patent/MX378007B/es unknown
- 2014-06-26 EP EP19207933.3A patent/EP3628661A1/en active Pending
- 2014-06-26 PL PL14818620T patent/PL3013796T3/pl unknown
- 2014-06-26 ES ES14818620T patent/ES2784489T3/es active Active
- 2014-06-26 LT LTEP14818620.8T patent/LT3013796T/lt unknown
-
2017
- 2017-05-19 AU AU2017203392A patent/AU2017203392B2/en active Active
-
2020
- 2020-03-12 CY CY20201100218T patent/CY1122742T1/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2016102313A (ru) | Биарильные производные в качестве агонистов gpr120 | |
| RU2017126199A (ru) | Биарильное производное в качестве агониста gpr120 | |
| JP2020023577A5 (ru) | ||
| RU2500673C2 (ru) | Гетероциклические ингибиторы мек и способы их применения | |
| FI3555076T3 (fi) | Uusia fenyylipropionihappojohdannaisia ja niiden käyttötapoja | |
| JP2013523803A5 (ru) | ||
| RU2489148C2 (ru) | Ингибитор активации stat3/5 | |
| JP2017511329A5 (ru) | ||
| RU2010110829A (ru) | Производные бензилбензола и способы их применения | |
| JP2013507350A5 (ru) | ||
| JP2011502958A5 (ru) | ||
| RU2019132254A (ru) | Гетероциклические соединения, пригодные в качестве дуальных ингибиторов atx/ca | |
| RU2009115830A (ru) | Пиридинкарбоксамиды в качестве ингибиторов 11-бета-hsd1 | |
| RU2016123449A (ru) | Октагидро конденсированные азадекалиновые модуляторы глюкокортикоидного рецептора | |
| RU2011147069A (ru) | НОВЫЙ АГОНИСТ β РЕЦЕПТОРА ТИРЕОИДНОГО ГОРМОНА | |
| RU2008108984A (ru) | Терапевтический агент от диабета | |
| IL161493A (en) | Pyrimidine derivatives and pharmaceutical compositions containing the same | |
| JP2018500360A5 (ru) | ||
| JP2008533137A5 (ru) | ||
| JP6413032B2 (ja) | 新規dgat2阻害剤 | |
| JP2019518036A5 (ru) | ||
| JP2008513405A5 (ru) | ||
| CN101203220A (zh) | 新用途 | |
| RU2019133530A (ru) | ПРОИЗВОДНЫЕ АМИДА В КАЧЕСТВЕ БЛОКАТОРОВ Nav1.7 И Nav1.8 | |
| JP2008516902A5 (ru) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HZ9A | Changing address for correspondence with an applicant |