DE60128239T2 - Oxazolylarylpropionsäure derivate und ihre verwendung als ppar agonisten - Google Patents

Info

Publication number

DE60128239T2

DE60128239T2 DE60128239T DE60128239T DE60128239T2 DE 60128239 T2 DE60128239 T2 DE 60128239T2 DE 60128239 T DE60128239 T DE 60128239T DE 60128239 T DE60128239 T DE 60128239T DE 60128239 T2 DE60128239 T2 DE 60128239T2

Authority

DE

Germany

Prior art keywords

methyl

phenyl

alkyl

ethoxy

acid

Prior art date

2000-08-23

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Lifetime

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• 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 title claims abstract description 19
• 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 title claims abstract description 19
• 239000002253 acid Substances 0.000 title claims description 26
• 239000000556 agonist Substances 0.000 title description 7
• 150000001875 compounds Chemical class 0.000 claims abstract description 260
• -1 thiophen-2,5-diyl Chemical group 0.000 claims abstract description 101
• 150000003839 salts Chemical class 0.000 claims abstract description 53
• 238000011282 treatment Methods 0.000 claims abstract description 34
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 32
• 239000012453 solvate Substances 0.000 claims abstract description 25
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 12
• 150000004677 hydrates Chemical class 0.000 claims abstract description 12
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
• 125000001624 naphthyl group Chemical group 0.000 claims abstract description 10
• 125000005493 quinolyl group Chemical group 0.000 claims abstract description 9
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
• 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
• 238000000034 method Methods 0.000 claims description 83
• 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 32
• 239000008103 glucose Substances 0.000 claims description 32
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 25
• 229910052739 hydrogen Inorganic materials 0.000 claims description 24
• 241000124008 Mammalia Species 0.000 claims description 21
• 229910052799 carbon Inorganic materials 0.000 claims description 21
• 210000004369 blood Anatomy 0.000 claims description 18
• 239000008280 blood Substances 0.000 claims description 18
• 210000002966 serum Anatomy 0.000 claims description 17
• 125000001544 thienyl group Chemical group 0.000 claims description 17
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 16
• 241001465754 Metazoa Species 0.000 claims description 16
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
• 239000003814 drug Substances 0.000 claims description 14
• 239000008194 pharmaceutical composition Substances 0.000 claims description 13
• 150000003626 triacylglycerols Chemical class 0.000 claims description 13
• 125000003118 aryl group Chemical group 0.000 claims description 12
• 238000004519 manufacturing process Methods 0.000 claims description 11
• 230000002265 prevention Effects 0.000 claims description 11
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 10
• 229910052736 halogen Inorganic materials 0.000 claims description 9
• 150000002367 halogens Chemical class 0.000 claims description 8
• 102000005962 receptors Human genes 0.000 claims description 8
• 108020003175 receptors Proteins 0.000 claims description 8
• 229920006395 saturated elastomer Polymers 0.000 claims description 8
• 208000011580 syndromic disease Diseases 0.000 claims description 8
• 102000015779 HDL Lipoproteins Human genes 0.000 claims description 7
• 108010010234 HDL Lipoproteins Proteins 0.000 claims description 7
• 102000007330 LDL Lipoproteins Human genes 0.000 claims description 7
• 108010007622 LDL Lipoproteins Proteins 0.000 claims description 7
• 238000002360 preparation method Methods 0.000 claims description 7
• 125000001424 substituent group Chemical group 0.000 claims description 7
• 241000282414 Homo sapiens Species 0.000 claims description 6
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
• 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
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• 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 4
• 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 description 3
• 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 3
• 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 3
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
• 238000002560 therapeutic procedure Methods 0.000 claims description 3
• TYWOJTKDVPFCLY-UHFFFAOYSA-N 2-(2-methoxyphenoxy)-2-methyl-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound COC1=CC=CC=C1OC(C)(C(O)=O)CC(C=C1)=CC=C1OCCC1=C(C)OC(C=2C=CC=CC=2)=N1 TYWOJTKDVPFCLY-UHFFFAOYSA-N 0.000 claims description 2
• 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
• 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 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
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• 239000003614 peroxisome proliferator Substances 0.000 claims description 2
• 125000001475 halogen functional group Chemical group 0.000 claims 5
• 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 2
• PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 claims 1
• SHUMAHDDIVFREX-UHFFFAOYSA-N 2-(3-chlorophenoxy)-2-methyl-3-[4-[2-[5-methyl-2-(1-methylcyclohexyl)-1,3-oxazol-4-yl]ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C2(C)CCCCC2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC(Cl)=C1 SHUMAHDDIVFREX-UHFFFAOYSA-N 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
• WRCNGANXBIBTMQ-UHFFFAOYSA-N 2-(3-thiophen-3-ylphenoxy)propanoic acid Chemical compound S1C=C(C=C1)C=1C=C(OC(C(=O)O)C)C=CC=1 WRCNGANXBIBTMQ-UHFFFAOYSA-N 0.000 claims 1
• 238000003745 diagnosis Methods 0.000 claims 1
• 230000002526 effect on cardiovascular system Effects 0.000 claims 1
• 125000001072 heteroaryl group Chemical group 0.000 abstract description 5
• 125000000592 heterocycloalkyl group Chemical group 0.000 abstract description 2
• 125000001188 haloalkyl group Chemical group 0.000 abstract 2
• 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 1
• 125000004446 heteroarylalkyl group Chemical group 0.000 abstract 1
• 125000003107 substituted aryl group Chemical group 0.000 abstract 1
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 172
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 162
• 238000005481 NMR spectroscopy Methods 0.000 description 152
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 133
• 239000000203 mixture Substances 0.000 description 118
• 239000000243 solution Substances 0.000 description 104
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 78
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 72
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 72
• 235000019439 ethyl acetate Nutrition 0.000 description 69
• 239000012074 organic phase Substances 0.000 description 65
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 61
• 239000000460 chlorine Substances 0.000 description 55
• 238000006243 chemical reaction Methods 0.000 description 54
• 235000002639 sodium chloride Nutrition 0.000 description 50
• 239000011541 reaction mixture Substances 0.000 description 47
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 46
• 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 description 46
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• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 44
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 44
• 239000011734 sodium Substances 0.000 description 41
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• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 31
• 239000012267 brine Substances 0.000 description 30
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 30
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 29
• 239000000047 product Substances 0.000 description 29
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 29
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• 239000004480 active ingredient Substances 0.000 description 28
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• 239000002904 solvent Substances 0.000 description 26
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• 238000010561 standard procedure Methods 0.000 description 24
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• 229940125396 insulin Drugs 0.000 description 23
• 239000003921 oil Substances 0.000 description 23
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• 239000003826 tablet Substances 0.000 description 21
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 20
• 239000012299 nitrogen atmosphere Substances 0.000 description 20
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 19
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 19
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
• 241000699670 Mus sp. Species 0.000 description 17
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• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
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• 125000004494 ethyl ester group Chemical group 0.000 description 13
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