AU2008241490B2 - Substituted biphenyl phenoxy-, thiophenyl- and aminophenylpropanoic acid GPR40 modulators - Google Patents
Substituted biphenyl phenoxy-, thiophenyl- and aminophenylpropanoic acid GPR40 modulators Download PDFInfo
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- AU2008241490B2 AU2008241490B2 AU2008241490A AU2008241490A AU2008241490B2 AU 2008241490 B2 AU2008241490 B2 AU 2008241490B2 AU 2008241490 A AU2008241490 A AU 2008241490A AU 2008241490 A AU2008241490 A AU 2008241490A AU 2008241490 B2 AU2008241490 B2 AU 2008241490B2
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- 101000912510 Homo sapiens Free fatty acid receptor 1 Proteins 0.000 title claims description 80
- 102100026148 Free fatty acid receptor 1 Human genes 0.000 title claims description 63
- -1 biphenyl phenoxy- Chemical class 0.000 title description 84
- HTCSFFGLRQDZDE-UHFFFAOYSA-N 2-azaniumyl-2-phenylpropanoate Chemical compound OC(=O)C(N)(C)C1=CC=CC=C1 HTCSFFGLRQDZDE-UHFFFAOYSA-N 0.000 title description 2
- 235000010290 biphenyl Nutrition 0.000 title description 2
- 239000004305 biphenyl Substances 0.000 title description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 358
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- 238000000034 method Methods 0.000 claims abstract description 91
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 40
- 239000003814 drug Substances 0.000 claims abstract description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 111
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 64
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 55
- 201000010099 disease Diseases 0.000 claims description 48
- 150000003839 salts Chemical class 0.000 claims description 43
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- 125000003545 alkoxy group Chemical group 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 26
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- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 14
- 206010018429 Glucose tolerance impaired Diseases 0.000 claims description 14
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- 206010023379 Ketoacidosis Diseases 0.000 claims description 14
- 208000007976 Ketosis Diseases 0.000 claims description 14
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 14
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- 229910052731 fluorine Inorganic materials 0.000 claims description 14
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- 239000003085 diluting agent Substances 0.000 claims description 8
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical group CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 6
- 229960003105 metformin Drugs 0.000 claims description 6
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical group O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims description 5
- 229940123464 Thiazolidinedione Drugs 0.000 claims description 5
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 5
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 230000003247 decreasing effect Effects 0.000 claims description 3
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 2
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- 230000000052 comparative effect Effects 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 443
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 317
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- 239000000243 solution Substances 0.000 description 147
- 229910052739 hydrogen Inorganic materials 0.000 description 128
- 238000003818 flash chromatography Methods 0.000 description 79
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 76
- 238000006243 chemical reaction Methods 0.000 description 75
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 72
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
- 239000011541 reaction mixture Substances 0.000 description 68
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 66
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- 229910002027 silica gel Inorganic materials 0.000 description 66
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- 239000000047 product Substances 0.000 description 62
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 62
- 239000012044 organic layer Substances 0.000 description 58
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 57
- 239000011734 sodium Substances 0.000 description 46
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 45
- 238000005481 NMR spectroscopy Methods 0.000 description 45
- 239000012230 colorless oil Substances 0.000 description 45
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 44
- 229910000024 caesium carbonate Inorganic materials 0.000 description 43
- 238000003556 assay Methods 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 38
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- 125000003342 alkenyl group Chemical group 0.000 description 28
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 27
- 238000003756 stirring Methods 0.000 description 25
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- 238000007792 addition Methods 0.000 description 24
- 210000004027 cell Anatomy 0.000 description 24
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 24
- 239000001257 hydrogen Substances 0.000 description 21
- 125000001424 substituent group Chemical group 0.000 description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 20
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 13
- 125000000304 alkynyl group Chemical group 0.000 description 13
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 11
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- MBSLQTQCXPHGIZ-SNVBAGLBSA-N ethyl (3s)-3-(4-hydroxyphenyl)pent-4-enoate Chemical compound CCOC(=O)C[C@@H](C=C)C1=CC=C(O)C=C1 MBSLQTQCXPHGIZ-SNVBAGLBSA-N 0.000 description 1
- LYPXTJZNUKHMLN-SNVBAGLBSA-N ethyl (3s)-3-(4-hydroxyphenyl)pent-4-ynoate Chemical compound CCOC(=O)C[C@@H](C#C)C1=CC=C(O)C=C1 LYPXTJZNUKHMLN-SNVBAGLBSA-N 0.000 description 1
- QYWBEPSEIJLPDM-IKJXHCRLSA-N ethyl (3s)-3-[4-(oxan-2-yloxy)phenyl]pent-4-ynoate Chemical compound C1=CC([C@H](C#C)CC(=O)OCC)=CC=C1OC1OCCCC1 QYWBEPSEIJLPDM-IKJXHCRLSA-N 0.000 description 1
- LQTPVHCITMKOGO-SANMLTNESA-N ethyl (3s)-3-[4-[[4-tert-butyl-3-(2-fluoro-5-methoxyphenyl)phenyl]methoxy]phenyl]-4-methylpent-4-enoate Chemical compound C1=CC([C@H](C(C)=C)CC(=O)OCC)=CC=C1OCC1=CC=C(C(C)(C)C)C(C=2C(=CC=C(OC)C=2)F)=C1 LQTPVHCITMKOGO-SANMLTNESA-N 0.000 description 1
- IEDNFTBGMSMNHN-JOCHJYFZSA-N ethyl (3s)-3-[4-[[4-tert-butyl-3-(2-fluoro-5-methoxyphenyl)phenyl]methoxy]phenyl]pent-4-enoate Chemical compound C1=CC([C@H](C=C)CC(=O)OCC)=CC=C1OCC1=CC=C(C(C)(C)C)C(C=2C(=CC=C(OC)C=2)F)=C1 IEDNFTBGMSMNHN-JOCHJYFZSA-N 0.000 description 1
- WBFAYDFXZOJNMW-JOCHJYFZSA-N ethyl (3s)-3-[4-[[4-tert-butyl-3-(2-fluoro-5-methoxyphenyl)phenyl]methoxy]phenyl]pent-4-ynoate Chemical compound C1=CC([C@H](C#C)CC(=O)OCC)=CC=C1OCC1=CC=C(C(C)(C)C)C(C=2C(=CC=C(OC)C=2)F)=C1 WBFAYDFXZOJNMW-JOCHJYFZSA-N 0.000 description 1
- GCHILWPFWGKQIR-FYWRMAATSA-N ethyl (e)-2-methyl-3-(4-phenylmethoxyphenyl)prop-2-enoate Chemical compound C1=CC(/C=C(\C)C(=O)OCC)=CC=C1OCC1=CC=CC=C1 GCHILWPFWGKQIR-FYWRMAATSA-N 0.000 description 1
- PFBQVGXIMLXCQB-VMPITWQZSA-N ethyl (e)-3-(4-nitrophenyl)prop-2-enoate Chemical compound CCOC(=O)\C=C\C1=CC=C([N+]([O-])=O)C=C1 PFBQVGXIMLXCQB-VMPITWQZSA-N 0.000 description 1
- NUDQJHVCDDPFAW-PYEVWLCESA-N ethyl (e,3r)-3-(4-hydroxyphenyl)hex-4-enoate Chemical compound CCOC(=O)C[C@H](\C=C\C)C1=CC=C(O)C=C1 NUDQJHVCDDPFAW-PYEVWLCESA-N 0.000 description 1
- PONMBLDGBOKUGW-UMESLIDUSA-N ethyl (e,3r)-3-[4-[[4-tert-butyl-3-(2-fluoro-5-methoxyphenyl)phenyl]methoxy]phenyl]hex-4-enoate Chemical compound C1=CC([C@@H](\C=C\C)CC(=O)OCC)=CC=C1OCC1=CC=C(C(C)(C)C)C(C=2C(=CC=C(OC)C=2)F)=C1 PONMBLDGBOKUGW-UMESLIDUSA-N 0.000 description 1
- STQYXULHNXTUBX-URWSZGRFSA-N ethyl (e,3s)-3-(4-hydroxyphenyl)hept-4-enoate Chemical compound CCOC(=O)C[C@@H](\C=C\CC)C1=CC=C(O)C=C1 STQYXULHNXTUBX-URWSZGRFSA-N 0.000 description 1
- MGOKXOQWIZLRLD-SLSCSEFVSA-N ethyl (e,3s)-3-[4-(oxan-2-yloxy)phenyl]-5-tributylstannylpent-4-enoate Chemical compound C1=CC([C@@H](CC(=O)OCC)C=C[Sn](CCCC)(CCCC)CCCC)=CC=C1OC1OCCCC1 MGOKXOQWIZLRLD-SLSCSEFVSA-N 0.000 description 1
- PGDHHLDASYGQOF-NPAMSPFLSA-N ethyl (e,3s)-3-[4-(oxan-2-yloxy)phenyl]hept-4-enoate Chemical compound C1=CC([C@H](\C=C\CC)CC(=O)OCC)=CC=C1OC1OCCCC1 PGDHHLDASYGQOF-NPAMSPFLSA-N 0.000 description 1
- JWVVLPLMVGQAPT-ZJABSEKFSA-N ethyl (e,3s)-3-[4-(oxan-2-yloxy)phenyl]hex-4-enoate Chemical compound C1=CC([C@H](\C=C\C)CC(=O)OCC)=CC=C1OC1OCCCC1 JWVVLPLMVGQAPT-ZJABSEKFSA-N 0.000 description 1
- DELZIBUHINXQOI-DZIAZQJWSA-N ethyl (e,3s)-3-[4-[[3-(2-butoxy-5-methoxyphenyl)-4-tert-butylphenyl]methoxy]phenyl]hex-4-enoate Chemical compound CCCCOC1=CC=C(OC)C=C1C1=CC(COC=2C=CC(=CC=2)[C@@H](CC(=O)OCC)\C=C\C)=CC=C1C(C)(C)C DELZIBUHINXQOI-DZIAZQJWSA-N 0.000 description 1
- ILXAYQYIWSBYQF-PVOYRIJTSA-N ethyl (e,3s)-3-[4-[[4-tert-butyl-3-(2-fluoro-5-methoxyphenyl)phenyl]methoxy]-2-methylphenyl]hex-4-enoate Chemical compound C1=C(C)C([C@H](\C=C\C)CC(=O)OCC)=CC=C1OCC1=CC=C(C(C)(C)C)C(C=2C(=CC=C(OC)C=2)F)=C1 ILXAYQYIWSBYQF-PVOYRIJTSA-N 0.000 description 1
- DELHQKRMPXXYCC-YHZGQTRVSA-N ethyl (e,3s)-3-[4-[[4-tert-butyl-3-(2-fluoro-5-methoxyphenyl)phenyl]methoxy]phenyl]hept-4-enoate Chemical compound C1=CC([C@H](\C=C\CC)CC(=O)OCC)=CC=C1OCC1=CC=C(C(C)(C)C)C(C=2C(=CC=C(OC)C=2)F)=C1 DELHQKRMPXXYCC-YHZGQTRVSA-N 0.000 description 1
- PONMBLDGBOKUGW-RXVLNYDTSA-N ethyl (e,3s)-3-[4-[[4-tert-butyl-3-(2-fluoro-5-methoxyphenyl)phenyl]methoxy]phenyl]hex-4-enoate Chemical compound C1=CC([C@H](\C=C\C)CC(=O)OCC)=CC=C1OCC1=CC=C(C(C)(C)C)C(C=2C(=CC=C(OC)C=2)F)=C1 PONMBLDGBOKUGW-RXVLNYDTSA-N 0.000 description 1
- XGMHPWKGEQZWCJ-XMUPNJDBSA-N ethyl (e,3s)-5-iodo-3-[4-(oxan-2-yloxy)phenyl]pent-4-enoate Chemical compound C1=CC([C@H](\C=C\I)CC(=O)OCC)=CC=C1OC1OCCCC1 XGMHPWKGEQZWCJ-XMUPNJDBSA-N 0.000 description 1
- PGFGDJRYGGZGOE-UHFFFAOYSA-N ethyl 3-(4-hydroxyphenyl)-2-methylpropanoate Chemical compound CCOC(=O)C(C)CC1=CC=C(O)C=C1 PGFGDJRYGGZGOE-UHFFFAOYSA-N 0.000 description 1
- HFAKUEIRAFSKCH-UHFFFAOYSA-N ethyl 3-(4-hydroxyphenyl)-4-methylpent-4-enoate Chemical compound CCOC(=O)CC(C(C)=C)C1=CC=C(O)C=C1 HFAKUEIRAFSKCH-UHFFFAOYSA-N 0.000 description 1
- VRDBGARLKWLHGR-UHFFFAOYSA-N ethyl 3-(4-hydroxyphenyl)butanoate Chemical compound CCOC(=O)CC(C)C1=CC=C(O)C=C1 VRDBGARLKWLHGR-UHFFFAOYSA-N 0.000 description 1
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- QOCJEBYBYIPHGJ-HMLKYZKVSA-N methyl (z,3r)-3-[4-[[4-tert-butyl-3-(2-fluoro-5-methoxyphenyl)phenyl]methoxy]phenyl]hept-4-enoate Chemical compound C1=CC([C@H](CC(=O)OC)\C=C/CC)=CC=C1OCC1=CC=C(C(C)(C)C)C(C=2C(=CC=C(OC)C=2)F)=C1 QOCJEBYBYIPHGJ-HMLKYZKVSA-N 0.000 description 1
- LIGPZXDXIBKQJZ-YLNCNTMDSA-N methyl (z,3r)-3-[4-[[4-tert-butyl-3-(2-fluoro-5-methoxyphenyl)phenyl]methoxy]phenyl]hex-4-enoate Chemical compound C1=CC([C@@H](\C=C/C)CC(=O)OC)=CC=C1OCC1=CC=C(C(C)(C)C)C(C=2C(=CC=C(OC)C=2)F)=C1 LIGPZXDXIBKQJZ-YLNCNTMDSA-N 0.000 description 1
- CICXXUQOZXKEBZ-BKSIFSGMSA-N methyl (z,3s)-3-(4-phenylmethoxyphenyl)hex-4-enoate Chemical compound C1=CC([C@H](\C=C/C)CC(=O)OC)=CC=C1OCC1=CC=CC=C1 CICXXUQOZXKEBZ-BKSIFSGMSA-N 0.000 description 1
- QOCJEBYBYIPHGJ-XXXZYALBSA-N methyl (z,3s)-3-[4-[[4-tert-butyl-3-(2-fluoro-5-methoxyphenyl)phenyl]methoxy]phenyl]hept-4-enoate Chemical compound C1=CC([C@@H](CC(=O)OC)\C=C/CC)=CC=C1OCC1=CC=C(C(C)(C)C)C(C=2C(=CC=C(OC)C=2)F)=C1 QOCJEBYBYIPHGJ-XXXZYALBSA-N 0.000 description 1
- FLYFKSWGNVAERO-UHFFFAOYSA-N methyl 2,2-dimethyl-3-(4-phenylmethoxyphenyl)propanoate Chemical compound C1=CC(CC(C)(C)C(=O)OC)=CC=C1OCC1=CC=CC=C1 FLYFKSWGNVAERO-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
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- Pregnancy & Childbirth (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US92501407P | 2007-04-16 | 2007-04-16 | |
| US60/925,014 | 2007-04-16 | ||
| PCT/US2008/004701 WO2008130514A1 (en) | 2007-04-16 | 2008-04-10 | Substituted biphenyl phenoxy-, thiophenyl- and aminophenylpropanoic acid gpr40 modulators |
Publications (2)
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| AU2008241490A1 AU2008241490A1 (en) | 2008-10-30 |
| AU2008241490B2 true AU2008241490B2 (en) | 2011-07-21 |
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| EP (1) | EP2139843B1 (enExample) |
| JP (1) | JP2010524932A (enExample) |
| AU (1) | AU2008241490B2 (enExample) |
| CA (1) | CA2683751C (enExample) |
| ES (1) | ES2446419T3 (enExample) |
| WO (1) | WO2008130514A1 (enExample) |
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| WO2007136573A2 (en) * | 2006-05-15 | 2007-11-29 | Merck & Co., Inc. | Antidiabetic bicyclic compounds |
| WO2008030618A1 (en) * | 2006-09-07 | 2008-03-13 | Amgen Inc. | Benzo-fused compounds for use in treating metabolic disorders |
| EP2064193A1 (en) * | 2006-09-07 | 2009-06-03 | Amgen, Inc | Heterocyclic gpr40 modulators |
-
2008
- 2008-04-10 ES ES08742774.6T patent/ES2446419T3/es active Active
- 2008-04-10 US US12/082,645 patent/US7572934B2/en not_active Expired - Fee Related
- 2008-04-10 CA CA2683751A patent/CA2683751C/en not_active Expired - Fee Related
- 2008-04-10 WO PCT/US2008/004701 patent/WO2008130514A1/en not_active Ceased
- 2008-04-10 JP JP2010504053A patent/JP2010524932A/ja active Pending
- 2008-04-10 AU AU2008241490A patent/AU2008241490B2/en not_active Ceased
- 2008-04-10 EP EP08742774.6A patent/EP2139843B1/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| ES2446419T3 (es) | 2014-03-07 |
| US20090111859A1 (en) | 2009-04-30 |
| EP2139843B1 (en) | 2013-12-25 |
| US7572934B2 (en) | 2009-08-11 |
| CA2683751A1 (en) | 2008-10-30 |
| WO2008130514A1 (en) | 2008-10-30 |
| AU2008241490A1 (en) | 2008-10-30 |
| EP2139843A1 (en) | 2010-01-06 |
| CA2683751C (en) | 2013-01-08 |
| JP2010524932A (ja) | 2010-07-22 |
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