PT1828137E - Derivados de tetra-hidroquinolina substituídos com 4- cicloalquilo e sua utilização enquanto medicamentos - Google Patents

Info

Publication number

PT1828137E

PT1828137E PT05820528T PT05820528T PT1828137E PT 1828137 E PT1828137 E PT 1828137E PT 05820528 T PT05820528 T PT 05820528T PT 05820528 T PT05820528 T PT 05820528T PT 1828137 E PT1828137 E PT 1828137E

Authority

PT

Portugal

Prior art keywords

compound

formula

inhibitors

solvates

salts

Prior art date

2004-12-18

Links

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• 239000003814 drug Substances 0.000 title claims description 13
• 125000000147 tetrahydroquinolinyl group Chemical class N1(CCCC2=CC=CC=C12)* 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 185
• 239000003112 inhibitor Substances 0.000 claims description 35
• 238000000034 method Methods 0.000 claims description 34
• 239000012453 solvate Chemical group 0.000 claims description 23
• 150000003839 salts Chemical group 0.000 claims description 22
• 238000011282 treatment Methods 0.000 claims description 22
• 102000004895 Lipoproteins Human genes 0.000 claims description 20
• 108090001030 Lipoproteins Proteins 0.000 claims description 20
• 239000002904 solvent Substances 0.000 claims description 20
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
• 238000002360 preparation method Methods 0.000 claims description 16
• 230000002265 prevention Effects 0.000 claims description 12
• 230000009467 reduction Effects 0.000 claims description 11
• 238000006722 reduction reaction Methods 0.000 claims description 11
• 239000005557 antagonist Substances 0.000 claims description 10
• 239000002253 acid Substances 0.000 claims description 9
• HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims description 8
• 201000001320 Atherosclerosis Diseases 0.000 claims description 8
• 239000003613 bile acid Substances 0.000 claims description 8
• 238000011917 diastereoselective reduction Methods 0.000 claims description 7
• 229940127470 Lipase Inhibitors Drugs 0.000 claims description 6
• 208000029078 coronary artery disease Diseases 0.000 claims description 6
• 230000008569 process Effects 0.000 claims description 6
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
• 208000032928 Dyslipidaemia Diseases 0.000 claims description 5
• 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 5
• 208000035150 Hypercholesterolemia Diseases 0.000 claims description 5
• 208000008589 Obesity Diseases 0.000 claims description 5
• 150000007513 acids Chemical class 0.000 claims description 5
• 239000000556 agonist Substances 0.000 claims description 5
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• 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 5
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• YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 claims description 3
• 229940127291 Calcium channel antagonist Drugs 0.000 claims description 3
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• 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims description 3
• BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 claims description 3
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• PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 claims description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 231100000252 nontoxic Toxicity 0.000 claims description 3
• 230000003000 nontoxic effect Effects 0.000 claims description 3
• 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 claims description 3
• 229940031439 squalene Drugs 0.000 claims description 3
• TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 claims description 3
• 208000023516 stroke disease Diseases 0.000 claims description 3
• ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 claims description 2
• 208000006011 Stroke Diseases 0.000 claims description 2
• 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 claims description 2
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
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• 125000006239 protecting group Chemical group 0.000 claims 2
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• 229960000258 corticotropin Drugs 0.000 claims 1
• 108010017796 epoxidase Proteins 0.000 claims 1
• 239000000106 platelet aggregation inhibitor Substances 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 84
• 239000000203 mixture Substances 0.000 description 65
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• 102000012336 Cholesterol Ester Transfer Proteins Human genes 0.000 description 49
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• 238000012360 testing method Methods 0.000 description 49
• -1 (5S) -4-cyclopentyl-3 - {(S) -fluoro- [4- (trifluoromethyl) phenyl] methyl} -4-isopropyl -7,7-dimethyl-5,6,7,8-tetrahydroquinoline-5-ol Chemical compound 0.000 description 34
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 33
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• AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 30
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• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
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• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 16
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