UA82108C2 - Похідні пірол-2,5-дитіону як модулятори х-рецептора печінки - Google Patents

Info

Publication number

UA82108C2

UA82108C2 UAA200600270A UAA200600270A UA82108C2 UA 82108 C2 UA82108 C2 UA 82108C2 UA A200600270 A UAA200600270 A UA A200600270A UA A200600270 A UAA200600270 A UA A200600270A UA 82108 C2 UA82108 C2 UA 82108C2

Authority

UA

Ukraine

Prior art keywords

phenyl

treatment

amino

compound

methoxyphenyl

Prior art date

2003-07-11

Links

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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
• DVUZQONFTJKFPV-UHFFFAOYSA-N pyrrole-2,5-dithione Chemical class S=C1NC(=S)C=C1 DVUZQONFTJKFPV-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 292
• 238000000034 method Methods 0.000 claims abstract description 57
• 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 16
• 208000032928 Dyslipidaemia Diseases 0.000 claims abstract description 14
• 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 9
• 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 239
• 239000012453 solvate Substances 0.000 claims description 239
• 238000011282 treatment Methods 0.000 claims description 116
• 230000002265 prevention Effects 0.000 claims description 74
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 72
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 68
• -1 3-pyridylmethyl Chemical group 0.000 claims description 53
• 239000003814 drug Substances 0.000 claims description 51
• 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 48
• 238000004519 manufacturing process Methods 0.000 claims description 43
• 241000124008 Mammalia Species 0.000 claims description 30
• 239000003153 chemical reaction reagent Substances 0.000 claims description 25
• 235000012000 cholesterol Nutrition 0.000 claims description 24
• 125000000217 alkyl group Chemical group 0.000 claims description 18
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
• 238000006243 chemical reaction Methods 0.000 claims description 14
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 11
• 239000007788 liquid Substances 0.000 claims description 11
• 208000035150 Hypercholesterolemia Diseases 0.000 claims description 10
• 208000017170 Lipid metabolism disease Diseases 0.000 claims description 9
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 8
• 206010003210 Arteriosclerosis Diseases 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 208000011775 arteriosclerosis disease Diseases 0.000 claims description 7
• 239000003795 chemical substances by application Substances 0.000 claims description 7
• 239000003085 diluting agent Substances 0.000 claims description 7
• 229940079593 drug Drugs 0.000 claims description 7
• 230000004968 inflammatory condition Effects 0.000 claims description 7
• 230000031891 intestinal absorption Effects 0.000 claims description 7
• 108010028554 LDL Cholesterol Proteins 0.000 claims description 6
• 238000008214 LDL Cholesterol Methods 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
• 102000005962 receptors Human genes 0.000 claims description 6
• 108020003175 receptors Proteins 0.000 claims description 6
• 230000004141 reverse cholesterol transport Effects 0.000 claims description 6
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
• 206010061218 Inflammation Diseases 0.000 claims description 5
• 125000001072 heteroaryl group Chemical group 0.000 claims description 5
• 230000004054 inflammatory process Effects 0.000 claims description 5
• 238000002560 therapeutic procedure Methods 0.000 claims description 5
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
• 102000007399 Nuclear hormone receptor Human genes 0.000 claims description 4
• 108020005497 Nuclear hormone receptor Proteins 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
• 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
• 125000001424 substituent group Chemical group 0.000 claims description 4
• 229940124597 therapeutic agent Drugs 0.000 claims description 4
• 206010020772 Hypertension Diseases 0.000 claims description 3
• 239000002671 adjuvant Substances 0.000 claims description 3
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
• 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 2
• 239000004480 active ingredient Substances 0.000 claims description 2
• 125000003545 alkoxy group Chemical group 0.000 claims description 2
• 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 229940088597 hormone Drugs 0.000 claims description 2
• 239000005556 hormone Substances 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
• 229910052757 nitrogen Inorganic materials 0.000 claims description 2
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 239000000969 carrier Substances 0.000 claims 1
• 125000001153 fluoro group Chemical group F* 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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• 239000000203 mixture Substances 0.000 description 56
• 229940002612 prodrug Drugs 0.000 description 49
• 239000000651 prodrug Substances 0.000 description 49
• 241001465754 Metazoa Species 0.000 description 48
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
• 239000000872 buffer Substances 0.000 description 27
• 239000003112 inhibitor Substances 0.000 description 27
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 26
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 24
• 239000005695 Ammonium acetate Substances 0.000 description 24
• 229940043376 ammonium acetate Drugs 0.000 description 24
• 235000019257 ammonium acetate Nutrition 0.000 description 24
• 238000004128 high performance liquid chromatography Methods 0.000 description 23
• 230000002829 reductive effect Effects 0.000 description 21
• 239000002904 solvent Substances 0.000 description 21
• 102100031051 Cysteine and glycine-rich protein 1 Human genes 0.000 description 16
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
• 239000011541 reaction mixture Substances 0.000 description 15
• 210000004027 cell Anatomy 0.000 description 11
• 239000003480 eluent Substances 0.000 description 11
• 238000004587 chromatography analysis Methods 0.000 description 10
• 238000001816 cooling Methods 0.000 description 10
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
• 201000010099 disease Diseases 0.000 description 9
• 239000000047 product Substances 0.000 description 9
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
• 230000000694 effects Effects 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
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• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
• UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 5
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• 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 5
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• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
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• FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 5
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• BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 5
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• XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 3
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