KR20060035748A - 간 ｘ 수용체 조절물질로서 피롤-2,5-디온 유도체 - Google Patents

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Publication number

KR20060035748A

KR20060035748A KR1020067000712A KR20067000712A KR20060035748A KR 20060035748 A KR20060035748 A KR 20060035748A KR 1020067000712 A KR1020067000712 A KR 1020067000712A KR 20067000712 A KR20067000712 A KR 20067000712A KR 20060035748 A KR20060035748 A KR 20060035748A

Authority

KR

South Korea

Prior art keywords

phenyl

treatment

amino

pyrrole

dione

Prior art date

2003-07-11

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.)

Withdrawn

Links

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• 102000005962 receptors Human genes 0.000 title description 6
• 108020003175 receptors Proteins 0.000 title description 6
• PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical class O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 title description 3
• 230000002440 hepatic effect Effects 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 284
• 238000011282 treatment Methods 0.000 claims abstract description 117
• 238000000034 method Methods 0.000 claims abstract description 85
• 102000004311 liver X receptors Human genes 0.000 claims abstract description 41
• 108090000865 liver X receptors Proteins 0.000 claims abstract description 41
• 208000024891 symptom Diseases 0.000 claims abstract description 39
• 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 29
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 20
• 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 18
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 18
• 208000032928 Dyslipidaemia Diseases 0.000 claims abstract description 16
• 208000017170 Lipid metabolism disease Diseases 0.000 claims abstract description 14
• 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 12
• 238000002560 therapeutic procedure Methods 0.000 claims abstract description 9
• 230000002757 inflammatory effect Effects 0.000 claims abstract description 8
• 206010022489 Insulin Resistance Diseases 0.000 claims abstract description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
• 150000002632 lipids Chemical class 0.000 claims abstract description 5
• 239000012453 solvate Substances 0.000 claims description 244
• 150000003839 salts Chemical class 0.000 claims description 226
• -1 2-methylthioethyl Chemical group 0.000 claims description 109
• 230000002265 prevention Effects 0.000 claims description 65
• 239000003814 drug Substances 0.000 claims description 52
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 50
• 238000004519 manufacturing process Methods 0.000 claims description 47
• 238000011321 prophylaxis Methods 0.000 claims description 38
• 241000124008 Mammalia Species 0.000 claims description 31
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
• 125000000217 alkyl group Chemical group 0.000 claims description 16
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 16
• 108010010234 HDL Lipoproteins Proteins 0.000 claims description 14
• 230000006872 improvement Effects 0.000 claims description 14
• 230000009467 reduction Effects 0.000 claims description 14
• 208000035150 Hypercholesterolemia Diseases 0.000 claims description 12
• 239000007788 liquid Substances 0.000 claims description 11
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 10
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 10
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 10
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 10
• 230000004141 reverse cholesterol transport Effects 0.000 claims description 10
• 108010028554 LDL Cholesterol Proteins 0.000 claims description 9
• 238000008214 LDL Cholesterol Methods 0.000 claims description 9
• 230000033227 intestinal cholesterol absorption Effects 0.000 claims description 9
• 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 8
• 108010023302 HDL Cholesterol Proteins 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 239000003085 diluting agent Substances 0.000 claims description 7
• FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 claims description 7
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 6
• FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 claims description 6
• 208000035475 disorder Diseases 0.000 claims description 6
• 125000001153 fluoro group Chemical group F* 0.000 claims description 6
• 206010061218 Inflammation Diseases 0.000 claims description 5
• 229910052794 bromium Inorganic materials 0.000 claims description 5
• 229910052801 chlorine Inorganic materials 0.000 claims description 5
• 238000011161 development Methods 0.000 claims description 5
• 125000001072 heteroaryl group Chemical group 0.000 claims description 5
• 230000004054 inflammatory process Effects 0.000 claims description 5
• 229910052740 iodine Inorganic materials 0.000 claims description 5
• 229910052757 nitrogen Inorganic materials 0.000 claims description 5
• 229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
• 229940124597 therapeutic agent Drugs 0.000 claims description 5
• 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 4
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
• 208000008589 Obesity Diseases 0.000 claims description 4
• DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims description 4
• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
• 125000004414 alkyl thio group Chemical group 0.000 claims description 4
• 235000020824 obesity Nutrition 0.000 claims description 4
• YARVSNLAHFZJKN-UHFFFAOYSA-N 1-(2-methoxyethyl)-3-(4-morpholin-4-ylanilino)-4-phenylpyrrole-2,5-dione Chemical compound C=1C=CC=CC=1C=1C(=O)N(CCOC)C(=O)C=1NC(C=C1)=CC=C1N1CCOCC1 YARVSNLAHFZJKN-UHFFFAOYSA-N 0.000 claims description 3
• YDUSKSCVRROBON-UHFFFAOYSA-N 1-(furan-3-ylmethyl)-3-(4-methoxyanilino)-4-phenylpyrrole-2,5-dione Chemical compound C1=CC(OC)=CC=C1NC(C1=O)=C(C=2C=CC=CC=2)C(=O)N1CC1=COC=C1 YDUSKSCVRROBON-UHFFFAOYSA-N 0.000 claims description 3
• NMRHBQAKGYVFQZ-UHFFFAOYSA-N 1-[(6-aminopyridin-3-yl)methyl]-3-(4-methoxyanilino)-4-phenylpyrrole-2,5-dione Chemical compound C1=CC(OC)=CC=C1NC(C1=O)=C(C=2C=CC=CC=2)C(=O)N1CC1=CC=C(N)N=C1 NMRHBQAKGYVFQZ-UHFFFAOYSA-N 0.000 claims description 3
• JDHWLVUZCIEPGC-UHFFFAOYSA-N 1-[(6-aminopyridin-3-yl)methyl]-3-(4-morpholin-4-ylanilino)-4-phenylpyrrole-2,5-dione Chemical compound C1=NC(N)=CC=C1CN1C(=O)C(C=2C=CC=CC=2)=C(NC=2C=CC(=CC=2)N2CCOCC2)C1=O JDHWLVUZCIEPGC-UHFFFAOYSA-N 0.000 claims description 3
• CUEFJLIVXWUITG-UHFFFAOYSA-N 1-[[4-(dimethylamino)phenyl]methyl]-3-(4-methoxyanilino)-4-phenylpyrrole-2,5-dione Chemical compound C1=CC(OC)=CC=C1NC(C1=O)=C(C=2C=CC=CC=2)C(=O)N1CC1=CC=C(N(C)C)C=C1 CUEFJLIVXWUITG-UHFFFAOYSA-N 0.000 claims description 3
• IJDRKXJGEDBBKZ-UHFFFAOYSA-N 3-(4-methoxyanilino)-1-(2-methoxyethyl)-4-phenylpyrrole-2,5-dione Chemical compound C=1C=CC=CC=1C=1C(=O)N(CCOC)C(=O)C=1NC1=CC=C(OC)C=C1 IJDRKXJGEDBBKZ-UHFFFAOYSA-N 0.000 claims description 3
• VWDGCBRPFUNZBZ-UHFFFAOYSA-N 3-(4-methoxyanilino)-1-(2-methylsulfanylethyl)-4-phenylpyrrole-2,5-dione Chemical compound C1=CC(OC)=CC=C1NC1=C(C=2C=CC=CC=2)C(=O)N(CCSC)C1=O VWDGCBRPFUNZBZ-UHFFFAOYSA-N 0.000 claims description 3
• LGKWEWTVEPDUAV-UHFFFAOYSA-N 3-(4-methoxyanilino)-1-(3-methoxypropyl)-4-phenylpyrrole-2,5-dione Chemical compound C=1C=CC=CC=1C=1C(=O)N(CCCOC)C(=O)C=1NC1=CC=C(OC)C=C1 LGKWEWTVEPDUAV-UHFFFAOYSA-N 0.000 claims description 3
• YMJWBXIXSZYSHH-UHFFFAOYSA-N 3-(4-methoxyanilino)-1-[(5-methyl-1,2-oxazol-3-yl)methyl]-4-phenylpyrrole-2,5-dione Chemical compound C1=CC(OC)=CC=C1NC(C1=O)=C(C=2C=CC=CC=2)C(=O)N1CC1=NOC(C)=C1 YMJWBXIXSZYSHH-UHFFFAOYSA-N 0.000 claims description 3
• OYBLWUWJHPWMTA-UHFFFAOYSA-N 3-(4-methoxyanilino)-4-phenyl-1-(2,2,2-trifluoroethyl)pyrrole-2,5-dione Chemical compound C1=CC(OC)=CC=C1NC1=C(C=2C=CC=CC=2)C(=O)N(CC(F)(F)F)C1=O OYBLWUWJHPWMTA-UHFFFAOYSA-N 0.000 claims description 3
• PIAPWUIDIJHWFZ-UHFFFAOYSA-N 3-(4-methoxyanilino)-4-phenyl-1-(3,3,3-trifluoropropyl)pyrrole-2,5-dione Chemical compound C1=CC(OC)=CC=C1NC1=C(C=2C=CC=CC=2)C(=O)N(CCC(F)(F)F)C1=O PIAPWUIDIJHWFZ-UHFFFAOYSA-N 0.000 claims description 3
• WMNVVLNVJBKEMR-UHFFFAOYSA-N 3-(4-methoxyanilino)-4-phenyl-1-(pyridin-2-ylmethyl)pyrrole-2,5-dione Chemical compound C1=CC(OC)=CC=C1NC(C1=O)=C(C=2C=CC=CC=2)C(=O)N1CC1=CC=CC=N1 WMNVVLNVJBKEMR-UHFFFAOYSA-N 0.000 claims description 3
• UUADKLHVJWMDLF-UHFFFAOYSA-N 3-(4-methoxyanilino)-4-phenyl-1-(pyridin-3-ylmethyl)pyrrole-2,5-dione Chemical compound C1=CC(OC)=CC=C1NC(C1=O)=C(C=2C=CC=CC=2)C(=O)N1CC1=CC=CN=C1 UUADKLHVJWMDLF-UHFFFAOYSA-N 0.000 claims description 3
• BWABNEHKDRQBPP-UHFFFAOYSA-N 3-(4-methoxyanilino)-4-phenyl-1-(pyridin-4-ylmethyl)pyrrole-2,5-dione Chemical compound C1=CC(OC)=CC=C1NC(C1=O)=C(C=2C=CC=CC=2)C(=O)N1CC1=CC=NC=C1 BWABNEHKDRQBPP-UHFFFAOYSA-N 0.000 claims description 3
• CGAORHFPTNYUGA-UHFFFAOYSA-N 3-(4-morpholin-4-ylanilino)-4-phenyl-1-(pyridin-3-ylmethyl)pyrrole-2,5-dione Chemical compound O=C1C(C=2C=CC=CC=2)=C(NC=2C=CC(=CC=2)N2CCOCC2)C(=O)N1CC1=CC=CN=C1 CGAORHFPTNYUGA-UHFFFAOYSA-N 0.000 claims description 3
• RPTBJJNNXVXBKM-UHFFFAOYSA-N 3-[(2-acetyl-1-benzofuran-5-yl)amino]-1-(2-methoxyethyl)-4-phenylpyrrole-2,5-dione Chemical compound O=C1N(CCOC)C(=O)C(NC=2C=C3C=C(OC3=CC=2)C(C)=O)=C1C1=CC=CC=C1 RPTBJJNNXVXBKM-UHFFFAOYSA-N 0.000 claims description 3
• QNMXSSQGJHJCLI-UHFFFAOYSA-N 3-[(2-acetyl-1-benzofuran-5-yl)amino]-4-phenyl-1-(pyridin-3-ylmethyl)pyrrole-2,5-dione Chemical compound C=1C=C2OC(C(=O)C)=CC2=CC=1NC(C1=O)=C(C=2C=CC=CC=2)C(=O)N1CC1=CC=CN=C1 QNMXSSQGJHJCLI-UHFFFAOYSA-N 0.000 claims description 3
• GRBPWTWSVBRHIQ-UHFFFAOYSA-N 3-[4-(difluoromethoxy)anilino]-1-(2-methoxyethyl)-4-phenylpyrrole-2,5-dione Chemical compound C=1C=CC=CC=1C=1C(=O)N(CCOC)C(=O)C=1NC1=CC=C(OC(F)F)C=C1 GRBPWTWSVBRHIQ-UHFFFAOYSA-N 0.000 claims description 3
• DIGLAFAKZCPPOA-UHFFFAOYSA-N 3-[4-(difluoromethoxy)anilino]-4-phenyl-1-(pyridin-3-ylmethyl)pyrrole-2,5-dione Chemical compound C1=CC(OC(F)F)=CC=C1NC(C1=O)=C(C=2C=CC=CC=2)C(=O)N1CC1=CC=CN=C1 DIGLAFAKZCPPOA-UHFFFAOYSA-N 0.000 claims description 3
• RAQFUEVZUPBBNT-UHFFFAOYSA-N 3-anilino-4-phenyl-1-(pyridin-3-ylmethyl)pyrrole-2,5-dione Chemical compound O=C1C(C=2C=CC=CC=2)=C(NC=2C=CC=CC=2)C(=O)N1CC1=CC=CN=C1 RAQFUEVZUPBBNT-UHFFFAOYSA-N 0.000 claims description 3
• DGYFPKIMHGNRES-UHFFFAOYSA-N 3-phenyl-1-(2,2,2-trifluoroethyl)-4-[4-(trifluoromethoxy)anilino]pyrrole-2,5-dione Chemical compound C=1C=CC=CC=1C=1C(=O)N(CC(F)(F)F)C(=O)C=1NC1=CC=C(OC(F)(F)F)C=C1 DGYFPKIMHGNRES-UHFFFAOYSA-N 0.000 claims description 3
• NGJSBKOSAZGTJL-UHFFFAOYSA-N 3-phenyl-1-(pyridin-3-ylmethyl)-4-[4-(trifluoromethoxy)anilino]pyrrole-2,5-dione Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(C1=O)=C(C=2C=CC=CC=2)C(=O)N1CC1=CC=CN=C1 NGJSBKOSAZGTJL-UHFFFAOYSA-N 0.000 claims description 3
• 239000002671 adjuvant Substances 0.000 claims description 3
• 230000033228 biological regulation Effects 0.000 claims description 3
• PVYOHJFFADYDDE-UHFFFAOYSA-N ethyl 2-[3-(4-methoxyanilino)-2,5-dioxo-4-phenylpyrrol-1-yl]acetate Chemical compound C=1C=CC=CC=1C=1C(=O)N(CC(=O)OCC)C(=O)C=1NC1=CC=C(OC)C=C1 PVYOHJFFADYDDE-UHFFFAOYSA-N 0.000 claims description 3
• UGTDRLZDYHDNHS-UHFFFAOYSA-N methyl 4-[[3-(4-methoxyanilino)-2,5-dioxo-4-phenylpyrrol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(=O)C(C=2C=CC=CC=2)=C(NC=2C=CC(OC)=CC=2)C1=O UGTDRLZDYHDNHS-UHFFFAOYSA-N 0.000 claims description 3
• FBPNLPUTIKFOLV-UHFFFAOYSA-N n-[4-[[1-(2-methoxyethyl)-2,5-dioxo-4-phenylpyrrol-3-yl]amino]phenyl]acetamide Chemical compound C=1C=CC=CC=1C=1C(=O)N(CCOC)C(=O)C=1NC1=CC=C(NC(C)=O)C=C1 FBPNLPUTIKFOLV-UHFFFAOYSA-N 0.000 claims description 3
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
• YQQHQHXKODBEOZ-UHFFFAOYSA-N 1-(2-methoxyethyl)-3-(4-methylsulfanylanilino)-4-phenylpyrrole-2,5-dione Chemical compound C=1C=CC=CC=1C=1C(=O)N(CCOC)C(=O)C=1NC1=CC=C(SC)C=C1 YQQHQHXKODBEOZ-UHFFFAOYSA-N 0.000 claims description 2
• 206010020772 Hypertension Diseases 0.000 claims description 2
• 125000005604 azodicarboxylate group Chemical group 0.000 claims description 2
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
• 125000001041 indolyl group Chemical group 0.000 claims description 2
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
• 150000003003 phosphines Chemical class 0.000 claims description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
• 125000001589 carboacyl group Chemical group 0.000 claims 2
• 229910052736 halogen Inorganic materials 0.000 claims 1
• 150000002367 halogens Chemical class 0.000 claims 1
• 208000001145 Metabolic Syndrome Diseases 0.000 abstract description 7
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