OA13035A - 3-(2-phenyl-oxazol-4-ylmethoxy)-cyclohexylmethoxy acetic acid derivatives and related compounds usedas PPAR modulators for treating type 2 diabetes a nd atherosclerosis. - Google Patents

Info

Publication number

OA13035A

OA13035A OA1200500248A OA1200500248A OA13035A OA 13035 A OA13035 A OA 13035A OA 1200500248 A OA1200500248 A OA 1200500248A OA 1200500248 A OA1200500248 A OA 1200500248A OA 13035 A OA13035 A OA 13035A

Authority

OA

OAPI

Prior art keywords

cis

alkyl

methyl

tert

phenyl

Prior art date

2003-02-27

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 185
• 208000001072 type 2 diabetes mellitus Diseases 0.000 title abstract 2
• 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 title description 29
• 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 title description 29
• 201000001320 Atherosclerosis Diseases 0.000 title description 5
• CQWYYUYAROQPOK-UHFFFAOYSA-N 2-[[3-[(2-phenyl-1,3-oxazol-4-yl)methoxy]cyclohexyl]methoxy]acetic acid Chemical class C1(=CC=CC=C1)C=1OC=C(N1)COC1CC(CCC1)COCC(=O)O CQWYYUYAROQPOK-UHFFFAOYSA-N 0.000 title description 2
• 150000003839 salts Chemical class 0.000 claims abstract description 20
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 16
• 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 abstract description 6
• 239000008103 glucose Substances 0.000 claims abstract description 6
• 238000004519 manufacturing process Methods 0.000 claims abstract description 3
• 230000004129 fatty acid metabolism Effects 0.000 claims abstract 2
• 239000000203 mixture Substances 0.000 claims description 149
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 59
• -1 (C1-C3)-alkyl-phenyl Chemical group 0.000 claims description 50
• 239000002253 acid Substances 0.000 claims description 29
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
• 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 20
• 238000011282 treatment Methods 0.000 claims description 17
• 229910052739 hydrogen Inorganic materials 0.000 claims description 16
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• 102000004877 Insulin Human genes 0.000 claims description 11
• 108090001061 Insulin Proteins 0.000 claims description 11
• 229940125396 insulin Drugs 0.000 claims description 10
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 9
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• 125000004432 carbon atom Chemical group C* 0.000 claims description 7
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
• 238000002156 mixing Methods 0.000 claims description 5
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 4
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
• 150000003254 radicals Chemical class 0.000 claims description 4
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
• 125000004429 atom Chemical group 0.000 claims description 3
• 125000002619 bicyclic group Chemical group 0.000 claims description 3
• 230000002349 favourable effect Effects 0.000 claims description 3
• 125000001072 heteroaryl group Chemical group 0.000 claims description 3
• 208000030159 metabolic disease Diseases 0.000 claims description 3
• 230000004060 metabolic process Effects 0.000 claims description 3
• 125000001624 naphthyl group Chemical group 0.000 claims description 3
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 2
• 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 2
• 235000019256 formaldehyde Nutrition 0.000 claims description 2
• 229930192474 thiophene Natural products 0.000 claims description 2
• 101100518413 Caenorhabditis elegans orc-2 gene Proteins 0.000 claims 1
• 208000001145 Metabolic Syndrome Diseases 0.000 claims 1
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 33
• 206010022489 Insulin Resistance Diseases 0.000 abstract 1
• 150000001242 acetic acid derivatives Chemical class 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 237
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 130
• 239000000243 solution Substances 0.000 description 120
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 90
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 88
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
• 229940093499 ethyl acetate Drugs 0.000 description 79
• 235000019439 ethyl acetate Nutrition 0.000 description 79
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 75
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 57
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 54
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 53
• 239000012074 organic phase Substances 0.000 description 50
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 49
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 48
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 44
• 235000019341 magnesium sulphate Nutrition 0.000 description 44
• 230000002829 reductive effect Effects 0.000 description 43
• 230000015572 biosynthetic process Effects 0.000 description 42
• 238000003786 synthesis reaction Methods 0.000 description 41
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 40
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 40
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 40
• 239000012071 phase Substances 0.000 description 39
• 239000003921 oil Substances 0.000 description 38
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 37
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 37
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 36
• 210000004027 cell Anatomy 0.000 description 35
• 239000002904 solvent Substances 0.000 description 34
• 239000000741 silica gel Substances 0.000 description 28
• 229910002027 silica gel Inorganic materials 0.000 description 28
• 229960001866 silicon dioxide Drugs 0.000 description 28
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
• 125000000062 cyclohexylmethoxy group Chemical group [H]C([H])(O*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 27
• 230000008569 process Effects 0.000 description 27
• 229920006395 saturated elastomer Polymers 0.000 description 27
• 239000008346 aqueous phase Substances 0.000 description 26
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 25
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 25
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 23
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 23
• 239000000556 agonist Substances 0.000 description 22
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 22
• 239000000725 suspension Substances 0.000 description 22
• 102000023984 PPAR alpha Human genes 0.000 description 21
• BNCNAQNTIYCMGB-UHFFFAOYSA-N 4-(iodomethyl)-2-(4-methylphenyl)-5-phenyl-1,3-oxazole Chemical compound C1=CC(C)=CC=C1C1=NC(CI)=C(C=2C=CC=CC=2)O1 BNCNAQNTIYCMGB-UHFFFAOYSA-N 0.000 description 20
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
• 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 description 20
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 19
• 239000013612 plasmid Substances 0.000 description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 18
• 239000011541 reaction mixture Substances 0.000 description 18
• 239000000047 product Substances 0.000 description 17
• 239000007787 solid Substances 0.000 description 17
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 16
• 238000007792 addition Methods 0.000 description 16
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 16
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 16
• 238000003556 assay Methods 0.000 description 15
• 229960004132 diethyl ether Drugs 0.000 description 15
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
• 238000003756 stirring Methods 0.000 description 15
• FSEUPUDHEBLWJY-HWKANZROSA-N diacetylmonoxime Chemical compound CC(=O)C(\C)=N\O FSEUPUDHEBLWJY-HWKANZROSA-N 0.000 description 14
• 238000004128 high performance liquid chromatography Methods 0.000 description 14
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 14
• YMKJZUSBDODQIC-NWDGAFQWSA-N tert-butyl 2-[[(1s,3r)-3-hydroxycyclohexyl]methoxy]-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)OC[C@H]1CCC[C@@H](O)C1 YMKJZUSBDODQIC-NWDGAFQWSA-N 0.000 description 14
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 13
• 229960000583 acetic acid Drugs 0.000 description 13
• 230000000694 effects Effects 0.000 description 13
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 12
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• 239000000126 substance Substances 0.000 description 12
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• 235000011054 acetic acid Nutrition 0.000 description 11
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 11
• 235000019260 propionic acid Nutrition 0.000 description 11
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• 239000005089 Luciferase Substances 0.000 description 10
• 102100038825 Peroxisome proliferator-activated receptor gamma Human genes 0.000 description 10
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
• 238000006243 chemical reaction Methods 0.000 description 10
• 239000001257 hydrogen Substances 0.000 description 10
• 229910000104 sodium hydride Inorganic materials 0.000 description 10
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• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
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• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 9
• NHGZEJHJHUHZDI-UHFFFAOYSA-N methyl 2-sulfanylbutanoate Chemical compound CCC(S)C(=O)OC NHGZEJHJHUHZDI-UHFFFAOYSA-N 0.000 description 9
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• SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 8
• 239000003112 inhibitor Substances 0.000 description 8
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• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
• CPGISPNRQJPVBR-OLZOCXBDSA-N tert-butyl 2-[[(1s,3r)-3-(hydroxymethyl)cyclohexyl]methoxy]-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)OC[C@H]1CCC[C@@H](CO)C1 CPGISPNRQJPVBR-OLZOCXBDSA-N 0.000 description 8
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• 102000040945 Transcription factor Human genes 0.000 description 5
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