JP2006519194A - ２型糖尿病およびアテローム性動脈硬化症の治療のためのｐｐａｒモジュレーターとしての３−（２−フェニル−オキサゾール−４−イルメトキシ）シクロヘキシルメトキシ酢酸誘導体および関連化合物 - Google Patents

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Publication number

JP2006519194A

JP2006519194A JP2006501886A JP2006501886A JP2006519194A JP 2006519194 A JP2006519194 A JP 2006519194A JP 2006501886 A JP2006501886 A JP 2006501886A JP 2006501886 A JP2006501886 A JP 2006501886A JP 2006519194 A JP2006519194 A JP 2006519194A

Authority

JP

Japan

Prior art keywords

alkyl

methyl

cis

tert

phenyl

Prior art date

2003-02-27

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.)

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 208
• 208000001072 type 2 diabetes mellitus Diseases 0.000 title claims abstract description 9
• 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 title description 28
• 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 title description 28
• 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 1
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 17
• 230000002265 prevention Effects 0.000 claims abstract description 15
• 150000003839 salts Chemical class 0.000 claims abstract description 13
• 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
• 206010022489 Insulin Resistance Diseases 0.000 claims abstract description 5
• 230000004129 fatty acid metabolism Effects 0.000 claims abstract 3
• 239000000203 mixture Substances 0.000 claims description 133
• -1 (C5-C11) -heteroaryl Chemical group 0.000 claims description 115
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 68
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 52
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
• 230000000694 effects Effects 0.000 claims description 17
• 239000003814 drug Substances 0.000 claims description 16
• 229910052739 hydrogen Inorganic materials 0.000 claims description 16
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 9
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 9
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
• 125000004432 carbon atom Chemical group C* 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
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
• 238000002156 mixing Methods 0.000 claims description 7
• 125000000217 alkyl group Chemical group 0.000 claims description 6
• 208000030159 metabolic disease Diseases 0.000 claims description 6
• 150000002632 lipids Chemical class 0.000 claims description 5
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
• 208000017170 Lipid metabolism disease Diseases 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
• 239000003472 antidiabetic agent Substances 0.000 claims description 4
• 125000003118 aryl group Chemical group 0.000 claims description 4
• 206010012601 diabetes mellitus Diseases 0.000 claims description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
• 208000032928 Dyslipidaemia Diseases 0.000 claims description 3
• 229940125708 antidiabetic agent Drugs 0.000 claims description 3
• 125000001072 heteroaryl group Chemical group 0.000 claims description 3
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 2
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• 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 2
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 2
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
• 229930192474 thiophene Natural products 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 24
• 239000000126 substance Substances 0.000 abstract description 10
• 238000002360 preparation method Methods 0.000 abstract description 6
• 150000001242 acetic acid derivatives Chemical class 0.000 abstract description 2
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 258
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 135
• 239000000243 solution Substances 0.000 description 126
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 123
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 108
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 100
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 95
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 67
• 239000012074 organic phase Substances 0.000 description 57
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 50
• 235000019341 magnesium sulphate Nutrition 0.000 description 50
• 229910001868 water Inorganic materials 0.000 description 50
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 41
• 230000015572 biosynthetic process Effects 0.000 description 41
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 40
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 40
• 239000012071 phase Substances 0.000 description 40
• 239000002904 solvent Substances 0.000 description 40
• 238000003786 synthesis reaction Methods 0.000 description 40
• 239000003921 oil Substances 0.000 description 39
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 38
• 210000004027 cell Anatomy 0.000 description 37
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 33
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 32
• 239000000741 silica gel Substances 0.000 description 31
• 229910002027 silica gel Inorganic materials 0.000 description 31
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
• 239000008346 aqueous phase Substances 0.000 description 29
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 28
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 27
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
• 102000023984 PPAR alpha Human genes 0.000 description 25
• 239000004480 active ingredient Substances 0.000 description 25
• 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 24
• 239000013612 plasmid Substances 0.000 description 24
• 239000000725 suspension Substances 0.000 description 24
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
• 108010016731 PPAR gamma Proteins 0.000 description 22
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• 239000000556 agonist Substances 0.000 description 21
• 239000011541 reaction mixture Substances 0.000 description 21
• 239000007787 solid Substances 0.000 description 21
• 108060001084 Luciferase Proteins 0.000 description 20
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 19
• 230000008569 process Effects 0.000 description 18
• 239000005089 Luciferase Substances 0.000 description 17
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 17
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 17
• 239000000047 product Substances 0.000 description 17
• 238000003756 stirring Methods 0.000 description 17
• 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 17
• 238000003556 assay Methods 0.000 description 16
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 16
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 16
• BCKQCTMFFSSHIB-UHFFFAOYSA-N CC1=CC=C(C=C1)C2=CC(=C(N2)C3=CC=CC=C3)CI Chemical compound CC1=CC=C(C=C1)C2=CC(=C(N2)C3=CC=CC=C3)CI BCKQCTMFFSSHIB-UHFFFAOYSA-N 0.000 description 15
• 102000000536 PPAR gamma Human genes 0.000 description 15
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
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• 229960000583 acetic acid Drugs 0.000 description 14
• FSEUPUDHEBLWJY-HWKANZROSA-N diacetylmonoxime Chemical compound CC(=O)C(\C)=N\O FSEUPUDHEBLWJY-HWKANZROSA-N 0.000 description 14
• 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 12
• 238000006243 chemical reaction Methods 0.000 description 12
• 239000012230 colorless oil Substances 0.000 description 12
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 12
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 11
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
• 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 11
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• 239000008194 pharmaceutical composition Substances 0.000 description 11
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• 239000001257 hydrogen Substances 0.000 description 10
• SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 10
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