UA82109C2 - Похідні пірол-2,5-дитіону як модулятори х-рецептора печінки - Google Patents

Info

Publication number

UA82109C2

UA82109C2 UAA200600272A UAA200600272A UA82109C2 UA 82109 C2 UA82109 C2 UA 82109C2 UA A200600272 A UAA200600272 A UA A200600272A UA A200600272 A UAA200600272 A UA A200600272A UA 82109 C2 UA82109 C2 UA 82109C2

Authority

UA

Ukraine

Prior art keywords

phenyl

treatment

amino

pyrrole

dione

Prior art date

2003-07-11

Links

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• Global Dossier
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• 102000004311 liver X receptors Human genes 0.000 title abstract 5
• 108090000865 liver X receptors Proteins 0.000 title abstract 5
• PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical class O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 288
• 238000000034 method Methods 0.000 claims abstract description 59
• 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 22
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 19
• 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 16
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 15
• 208000032928 Dyslipidaemia Diseases 0.000 claims abstract description 14
• 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 10
• 206010022489 Insulin Resistance Diseases 0.000 claims abstract description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
• 150000002632 lipids Chemical class 0.000 claims abstract description 6
• 150000003839 salts Chemical class 0.000 claims description 241
• 239000012453 solvate Substances 0.000 claims description 240
• 238000011282 treatment Methods 0.000 claims description 117
• -1 2-methylthioethyl Chemical group 0.000 claims description 93
• 230000002265 prevention Effects 0.000 claims description 74
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 59
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 54
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 52
• 239000003814 drug Substances 0.000 claims description 52
• 238000004519 manufacturing process Methods 0.000 claims description 44
• 241000282414 Homo sapiens Species 0.000 claims description 42
• 241000124008 Mammalia Species 0.000 claims description 30
• 235000012000 cholesterol Nutrition 0.000 claims description 27
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
• 125000000217 alkyl group Chemical group 0.000 claims description 18
• 238000006243 chemical reaction Methods 0.000 claims description 16
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 15
• 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
• 208000035150 Hypercholesterolemia Diseases 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
• 208000017170 Lipid metabolism disease Diseases 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
• 206010003210 Arteriosclerosis Diseases 0.000 claims description 8
• FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 claims description 8
• 229940079593 drug Drugs 0.000 claims description 8
• FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 208000011775 arteriosclerosis disease Diseases 0.000 claims description 7
• 239000003085 diluting agent Substances 0.000 claims description 7
• 230000004968 inflammatory condition Effects 0.000 claims description 7
• 230000031891 intestinal absorption Effects 0.000 claims description 7
• 206010061218 Inflammation Diseases 0.000 claims description 6
• 208000035475 disorder Diseases 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• 239000011737 fluorine Substances 0.000 claims description 6
• 230000004054 inflammatory process Effects 0.000 claims description 6
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
• 108010028554 LDL Cholesterol Proteins 0.000 claims description 5
• 238000008214 LDL Cholesterol Methods 0.000 claims description 5
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000001072 heteroaryl group Chemical group 0.000 claims description 5
• 229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
• 238000002560 therapeutic procedure Methods 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
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 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
• 125000004414 alkyl thio group Chemical group 0.000 claims description 4
• 125000001589 carboacyl group Chemical group 0.000 claims description 4
• 238000011161 development Methods 0.000 claims description 4
• 235000020824 obesity Nutrition 0.000 claims description 4
• 230000002441 reversible effect Effects 0.000 claims description 4
• 125000001424 substituent group Chemical group 0.000 claims description 4
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• 239000002671 adjuvant Substances 0.000 claims description 3
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
• METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 3
• 229940088597 hormone Drugs 0.000 claims description 3
• 239000005556 hormone Substances 0.000 claims description 3
• 229910052757 nitrogen Inorganic materials 0.000 claims description 3
• 230000004141 reverse cholesterol transport Effects 0.000 claims description 3
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 2
• 239000004480 active ingredient Substances 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
• 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
• 239000000969 carrier Substances 0.000 claims 1
• 230000033227 intestinal cholesterol absorption Effects 0.000 claims 1
• 238000012876 topography Methods 0.000 claims 1
• 208000001145 Metabolic Syndrome Diseases 0.000 abstract description 7
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 abstract description 7
• 230000001225 therapeutic effect Effects 0.000 abstract description 4
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• 239000000651 prodrug Substances 0.000 description 54
• 229940002612 prodrug Drugs 0.000 description 54
• 241001465754 Metazoa Species 0.000 description 48
• 239000011541 reaction mixture Substances 0.000 description 40
• 239000000203 mixture Substances 0.000 description 35
• 239000000872 buffer Substances 0.000 description 29
• 239000003112 inhibitor Substances 0.000 description 28
• 238000004128 high performance liquid chromatography Methods 0.000 description 27
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 26
• 239000005695 Ammonium acetate Substances 0.000 description 26
• 229940043376 ammonium acetate Drugs 0.000 description 26
• 235000019257 ammonium acetate Nutrition 0.000 description 26
• 238000001816 cooling Methods 0.000 description 22
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
• 238000005481 NMR spectroscopy Methods 0.000 description 20
• 102100031051 Cysteine and glycine-rich protein 1 Human genes 0.000 description 18
• 239000000243 solution Substances 0.000 description 18
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• 238000010438 heat treatment Methods 0.000 description 12
• 210000004027 cell Anatomy 0.000 description 11
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• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
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• 201000010099 disease Diseases 0.000 description 8
• 239000012362 glacial acetic acid Substances 0.000 description 8
• XTFROYHLJUHJII-UHFFFAOYSA-N 3-chloro-4-phenylfuran-2,5-dione Chemical compound O=C1OC(=O)C(Cl)=C1C1=CC=CC=C1 XTFROYHLJUHJII-UHFFFAOYSA-N 0.000 description 7
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• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
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• ZTADJGZYOQARLX-UHFFFAOYSA-N 3-chloro-4-phenyl-1-(pyridin-3-ylmethyl)pyrrole-2,5-dione Chemical compound O=C1C(Cl)=C(C=2C=CC=CC=2)C(=O)N1CC1=CC=CN=C1 ZTADJGZYOQARLX-UHFFFAOYSA-N 0.000 description 5
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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 description 5
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• 102100030988 Angiotensin-converting enzyme Human genes 0.000 description 4
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
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