PT1313716E - Derivados do ácido oxazolil-arilpropiónico e a sua utilização como agonistas do ppar - Google Patents

Info

Publication number

PT1313716E

PT1313716E PT01963733T PT01963733T PT1313716E PT 1313716 E PT1313716 E PT 1313716E PT 01963733 T PT01963733 T PT 01963733T PT 01963733 T PT01963733 T PT 01963733T PT 1313716 E PT1313716 E PT 1313716E

Authority

PT

Portugal

Prior art keywords

methyl

phenyl

alkyl

oxazol

ethoxy

Prior art date

2000-08-23

Links

• Espacenet
• Global Dossier
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• 239000002253 acid Substances 0.000 title claims description 26
• 239000000556 agonist Substances 0.000 title description 6
• 101150014691 PPARA gene Proteins 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 274
• -1 thiophen-2,5-diyl Chemical group 0.000 claims abstract description 182
• 150000003839 salts Chemical class 0.000 claims abstract description 54
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 33
• 239000012453 solvate Substances 0.000 claims abstract description 26
• 238000011282 treatment Methods 0.000 claims abstract description 24
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 13
• 150000004677 hydrates Chemical class 0.000 claims abstract description 13
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 11
• 125000001624 naphthyl group Chemical group 0.000 claims abstract description 10
• 125000005493 quinolyl group Chemical group 0.000 claims abstract description 9
• 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 7
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 5
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 4
• 125000001188 haloalkyl group Chemical group 0.000 claims abstract 3
• 238000000034 method Methods 0.000 claims description 87
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 64
• 229920006395 saturated elastomer Polymers 0.000 claims description 38
• 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 description 34
• 239000008103 glucose Substances 0.000 claims description 34
• 210000002966 serum Anatomy 0.000 claims description 21
• 125000001544 thienyl group Chemical group 0.000 claims description 20
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 19
• 241000124008 Mammalia Species 0.000 claims description 19
• 210000004369 blood Anatomy 0.000 claims description 19
• 239000008280 blood Substances 0.000 claims description 19
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 18
• 229910052736 halogen Inorganic materials 0.000 claims description 18
• 241001465754 Metazoa Species 0.000 claims description 16
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
• 239000008194 pharmaceutical composition Substances 0.000 claims description 14
• 102000005962 receptors Human genes 0.000 claims description 13
• 108020003175 receptors Proteins 0.000 claims description 13
• 150000003626 triacylglycerols Chemical class 0.000 claims description 13
• 238000004519 manufacturing process Methods 0.000 claims description 11
• 230000000858 peroxisomal effect Effects 0.000 claims description 10
• 230000035755 proliferation Effects 0.000 claims description 10
• 125000003118 aryl group Chemical group 0.000 claims description 9
• 239000003814 drug Substances 0.000 claims description 9
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
• 150000002367 halogens Chemical class 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 7
• 108010010234 HDL Lipoproteins Proteins 0.000 claims description 7
• 102000015779 HDL Lipoproteins Human genes 0.000 claims description 7
• 108010007622 LDL Lipoproteins Proteins 0.000 claims description 7
• 102000007330 LDL Lipoproteins Human genes 0.000 claims description 7
• 125000001424 substituent group Chemical group 0.000 claims description 7
• 208000011580 syndromic disease Diseases 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• 239000001257 hydrogen Substances 0.000 claims description 6
• 229910052739 hydrogen Inorganic materials 0.000 claims description 6
• 229910052799 carbon Inorganic materials 0.000 claims description 5
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
• JSTSZHVRXHMZQK-NDEPHWFRSA-N (2s)-2-methyl-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-phenoxypropanoic acid Chemical compound O([C@@](C)(CC1=CC=C(C=C1)OCCC=1N=C(OC=1C)C=1C=CC=CC=1)C(O)=O)C1=CC=CC=C1 JSTSZHVRXHMZQK-NDEPHWFRSA-N 0.000 claims description 4
• KWSPYUOBNIMILB-UHFFFAOYSA-N 2-methyl-3-[4-[2-(5-methyl-2-thiophen-2-yl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-phenoxypropanoic acid Chemical compound CC=1OC(C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC=C1 KWSPYUOBNIMILB-UHFFFAOYSA-N 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• KWSPYUOBNIMILB-SANMLTNESA-N (2s)-2-methyl-3-[4-[2-(5-methyl-2-thiophen-2-yl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-phenoxypropanoic acid Chemical compound O([C@@](C)(CC1=CC=C(C=C1)OCCC=1N=C(OC=1C)C=1SC=CC=1)C(O)=O)C1=CC=CC=C1 KWSPYUOBNIMILB-SANMLTNESA-N 0.000 claims description 3
• JSTSZHVRXHMZQK-UHFFFAOYSA-N 2-methyl-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-phenoxypropanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC=C1 JSTSZHVRXHMZQK-UHFFFAOYSA-N 0.000 claims description 3
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• UCNGNXHBTZPMDE-LJAQVGFWSA-N (2s)-3-[4-[2-(2-cyclohexyl-5-methyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-methyl-2-(4-methylphenoxy)propanoic acid Chemical compound O([C@@](C)(CC1=CC=C(C=C1)OCCC=1N=C(OC=1C)C1CCCCC1)C(O)=O)C1=CC=C(C)C=C1 UCNGNXHBTZPMDE-LJAQVGFWSA-N 0.000 claims description 2
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• GYDYGMALAVXYJR-UHFFFAOYSA-N 2-methyl-2-(2-methylphenoxy)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC=C1C GYDYGMALAVXYJR-UHFFFAOYSA-N 0.000 claims description 2
• XNNSVDBLAAWIHF-UHFFFAOYSA-N 2-methyl-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-quinolin-6-yloxypropanoic acid Chemical compound N=1C(CCOC=2C=CC(CC(C)(OC=3C=C4C=CC=NC4=CC=3)C(O)=O)=CC=2)=C(C)OC=1C1=CC=CC=C1 XNNSVDBLAAWIHF-UHFFFAOYSA-N 0.000 claims description 2
• UYZRCSAVQYPXAQ-UHFFFAOYSA-N 2-methyl-3-[4-[2-[5-methyl-2-(1-methylcyclohexyl)-1,3-oxazol-4-yl]ethoxy]phenyl]-2-(2-methylphenoxy)propanoic acid Chemical compound CC=1OC(C2(C)CCCCC2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC=C1C UYZRCSAVQYPXAQ-UHFFFAOYSA-N 0.000 claims description 2
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• KLYSGRRZNYRRDA-UHFFFAOYSA-N 3-[4-[2-(2-cyclohexyl-5-methyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-(2-methoxyphenoxy)-2-methylpropanoic acid Chemical compound COC1=CC=CC=C1OC(C)(C(O)=O)CC(C=C1)=CC=C1OCCC1=C(C)OC(C2CCCCC2)=N1 KLYSGRRZNYRRDA-UHFFFAOYSA-N 0.000 claims description 2
• ZJASNYLZHSZJRM-UHFFFAOYSA-N 3-[4-[2-(2-cyclohexyl-5-methyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-methyl-2-(2-methylphenoxy)propanoic acid Chemical compound CC=1OC(C2CCCCC2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC=C1C ZJASNYLZHSZJRM-UHFFFAOYSA-N 0.000 claims description 2
• UCNGNXHBTZPMDE-UHFFFAOYSA-N 3-[4-[2-(2-cyclohexyl-5-methyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-methyl-2-(4-methylphenoxy)propanoic acid Chemical compound CC=1OC(C2CCCCC2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=C(C)C=C1 UCNGNXHBTZPMDE-UHFFFAOYSA-N 0.000 claims description 2
• AOMGCCNQPCIIJP-UHFFFAOYSA-N 3-[4-[2-(2-cyclohexyl-5-methyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-methyl-2-quinolin-6-yloxypropanoic acid Chemical compound N=1C(CCOC=2C=CC(CC(C)(OC=3C=C4C=CC=NC4=CC=3)C(O)=O)=CC=2)=C(C)OC=1C1CCCCC1 AOMGCCNQPCIIJP-UHFFFAOYSA-N 0.000 claims description 2
• 125000005843 halogen group Chemical group 0.000 claims 8
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 4
• 238000002560 therapeutic procedure Methods 0.000 claims 2
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
• QYHAWNLDQLOSNT-UHFFFAOYSA-N 2-(3-chlorophenoxy)-3-[4-[2-(2-cyclohexyl-5-methyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-methylpropanoic acid Chemical compound CC=1OC(C2CCCCC2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC(Cl)=C1 QYHAWNLDQLOSNT-UHFFFAOYSA-N 0.000 claims 1
• UGFDMEAQMIZMJH-UHFFFAOYSA-N 2-methyl-2-(2-methylphenoxy)-3-[4-[2-(5-methyl-2-thiophen-2-yl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC=C1C UGFDMEAQMIZMJH-UHFFFAOYSA-N 0.000 claims 1
• 238000003745 diagnosis Methods 0.000 claims 1
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• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract description 3
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• 235000002639 sodium chloride Nutrition 0.000 description 75
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 74
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 70
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• 239000012074 organic phase Substances 0.000 description 66
• 235000019439 ethyl acetate Nutrition 0.000 description 65
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 64
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