CA2160092A1 - Antihypertriglyceridemic composition - Google Patents

Info

Publication number

CA2160092A1

CA2160092A1 CA002160092A CA2160092A CA2160092A1 CA 2160092 A1 CA2160092 A1 CA 2160092A1 CA 002160092 A CA002160092 A CA 002160092A CA 2160092 A CA2160092 A CA 2160092A CA 2160092 A1 CA2160092 A1 CA 2160092A1

Authority

CA

Canada

Prior art keywords

substituted

group

ring

composition

antihypertriglyceridemic

Prior art date

1994-10-07

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 239000000203 mixture Substances 0.000 title claims abstract description 64
• 230000001346 anti-hypertriglyceridemic effect Effects 0.000 title claims abstract description 45
• 125000001424 substituent group Chemical group 0.000 claims abstract description 90
• 150000001875 compounds Chemical class 0.000 claims abstract description 67
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 56
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 42
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 35
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 30
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 26
• 150000003839 salts Chemical class 0.000 claims abstract description 24
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 22
• 238000011282 treatment Methods 0.000 claims abstract description 18
• UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims abstract description 18
• 201000005577 familial hyperlipidemia Diseases 0.000 claims abstract description 17
• 238000011321 prophylaxis Methods 0.000 claims abstract description 15
• 125000003277 amino group Chemical group 0.000 claims abstract description 13
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 12
• 208000006575 hypertriglyceridemia Diseases 0.000 claims abstract description 12
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims abstract description 7
• 125000005330 8 membered heterocyclic group Chemical group 0.000 claims abstract description 7
• 239000000470 constituent Substances 0.000 claims abstract description 7
• 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 12
• -1 1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid compound Chemical class 0.000 claims description 96
• 125000000217 alkyl group Chemical group 0.000 claims description 68
• 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 37
• 229910052736 halogen Inorganic materials 0.000 claims description 22
• 150000002367 halogens Chemical class 0.000 claims description 22
• 235000012000 cholesterol Nutrition 0.000 claims description 19
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• 238000000034 method Methods 0.000 claims description 13
• 239000002552 dosage form Substances 0.000 claims description 12
• 125000002947 alkylene group Chemical group 0.000 claims description 10
• 150000002632 lipids Chemical class 0.000 claims description 10
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 9
• 230000015572 biosynthetic process Effects 0.000 claims description 8
• 239000003112 inhibitor Substances 0.000 claims description 7
• 159000000000 sodium salts Chemical group 0.000 claims description 7
• 239000003085 diluting agent Substances 0.000 claims description 6
• 239000001257 hydrogen Substances 0.000 claims description 6
• 229910052739 hydrogen Inorganic materials 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• KNWJPGLBKMPTEW-TZIWHRDSSA-N 2-[(3r,5s)-7-chloro-5-(2,3-dimethoxyphenyl)-1-(2,2-dimethylpropyl)-2-oxo-5h-4,1-benzoxazepin-3-yl]acetic acid Chemical compound COC1=CC=CC([C@@H]2C3=CC(Cl)=CC=C3N(CC(C)(C)C)C(=O)[C@@H](CC(O)=O)O2)=C1OC KNWJPGLBKMPTEW-TZIWHRDSSA-N 0.000 claims description 5
• LNLKTCJADHSICK-IFMALSPDSA-N 2-[(3r,5s)-7-chloro-5-(2,4-dimethoxyphenyl)-1-(2,2-dimethylpropyl)-2-oxo-5h-4,1-benzoxazepin-3-yl]acetic acid Chemical compound COC1=CC(OC)=CC=C1[C@@H]1C2=CC(Cl)=CC=C2N(CC(C)(C)C)C(=O)[C@@H](CC(O)=O)O1 LNLKTCJADHSICK-IFMALSPDSA-N 0.000 claims description 5
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
• 238000002156 mixing Methods 0.000 claims description 5
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• ARHDATYUGGRDEW-FYYLOGMGSA-N 2-[(3r,5s)-7-chloro-1-(2,2-dimethylpropyl)-5-(4-ethoxy-2-methoxyphenyl)-2-oxo-5h-4,1-benzoxazepin-3-yl]acetic acid Chemical compound COC1=CC(OCC)=CC=C1[C@@H]1C2=CC(Cl)=CC=C2N(CC(C)(C)C)C(=O)[C@@H](CC(O)=O)O1 ARHDATYUGGRDEW-FYYLOGMGSA-N 0.000 claims description 4
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 4
• 125000004122 cyclic group Chemical group 0.000 claims description 4
• 238000004898 kneading Methods 0.000 claims description 4
• 239000003529 anticholesteremic agent Substances 0.000 claims description 3
• 229940127226 anticholesterol agent Drugs 0.000 claims description 3
• 229910021645 metal ion Inorganic materials 0.000 claims description 3
• 239000000829 suppository Substances 0.000 claims description 3
• 125000000464 thioxo group Chemical group S=* 0.000 claims description 3
• 102000005782 Squalene Monooxygenase Human genes 0.000 claims description 2
• 108020003891 Squalene monooxygenase Proteins 0.000 claims description 2
• 239000003524 antilipemic agent Substances 0.000 claims description 2
• 229920000080 bile acid sequestrant Polymers 0.000 claims description 2
• 230000001906 cholesterol absorption Effects 0.000 claims description 2
• 229940125753 fibrate Drugs 0.000 claims description 2
• 229960003512 nicotinic acid Drugs 0.000 claims description 2
• 235000001968 nicotinic acid Nutrition 0.000 claims description 2
• 239000011664 nicotinic acid Substances 0.000 claims description 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
• BHDQOMHFEOHAQK-AZUAARDMSA-N 2-[(3s,5s)-7-chloro-5-(2-chlorophenyl)-1-(2,2-dimethylpropyl)-2-oxo-5h-4,1-benzoxazepin-3-yl]acetic acid Chemical compound C1([C@@H]2C3=CC(Cl)=CC=C3N(C([C@H](CC(O)=O)O2)=O)CC(C)(C)C)=CC=CC=C1Cl BHDQOMHFEOHAQK-AZUAARDMSA-N 0.000 claims 1
• 241000124008 Mammalia Species 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• 230000000694 effects Effects 0.000 abstract description 14
• 125000003118 aryl group Chemical group 0.000 description 31
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 30
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 28
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 27
• 239000000460 chlorine Substances 0.000 description 26
• 239000003826 tablet Substances 0.000 description 25
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 24
• 229910052801 chlorine Inorganic materials 0.000 description 24
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 20
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 20
• 229910052794 bromium Inorganic materials 0.000 description 20
• 150000002430 hydrocarbons Chemical group 0.000 description 20
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 19
• 239000011737 fluorine Substances 0.000 description 19
• 229910052731 fluorine Inorganic materials 0.000 description 19
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 19
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 18
• 239000011630 iodine Substances 0.000 description 18
• 229910052740 iodine Inorganic materials 0.000 description 18
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 18
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 17
• 125000003710 aryl alkyl group Chemical group 0.000 description 16
• 125000003545 alkoxy group Chemical group 0.000 description 15
• 235000019359 magnesium stearate Nutrition 0.000 description 15
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 15
• 239000002775 capsule Substances 0.000 description 14
• 238000005469 granulation Methods 0.000 description 14
• 230000003179 granulation Effects 0.000 description 14
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 13
• 229920000168 Microcrystalline cellulose Polymers 0.000 description 13
• 125000002252 acyl group Chemical group 0.000 description 13
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
• 125000000753 cycloalkyl group Chemical group 0.000 description 13
• 239000008101 lactose Substances 0.000 description 13
• 235000019813 microcrystalline cellulose Nutrition 0.000 description 13
• 239000008108 microcrystalline cellulose Substances 0.000 description 13
• 229940016286 microcrystalline cellulose Drugs 0.000 description 13
• 229940126062 Compound A Drugs 0.000 description 12
• NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 12
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
• 239000007924 injection Substances 0.000 description 11
• 238000002347 injection Methods 0.000 description 11
• 201000010099 disease Diseases 0.000 description 10
• 238000012360 testing method Methods 0.000 description 10
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
• 229920002261 Corn starch Polymers 0.000 description 9
• 108010023302 HDL Cholesterol Proteins 0.000 description 9
• 239000008120 corn starch Substances 0.000 description 9
• 229940079593 drug Drugs 0.000 description 9
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 9
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
• 125000000392 cycloalkenyl group Chemical group 0.000 description 8
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
• 239000000243 solution Substances 0.000 description 8
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 7
• 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 7
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 7
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 7
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• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
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• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
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• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
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• DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 4
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
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• IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 description 4
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• 150000003573 thiols Chemical class 0.000 description 4
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• 102000004877 Insulin Human genes 0.000 description 3
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• 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 3
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• 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 3
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• 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
• 125000001589 carboacyl group Chemical group 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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• 235000014113 dietary fatty acids Nutrition 0.000 description 3
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• 239000000194 fatty acid Substances 0.000 description 3
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