HUT73422A

HUT73422A - Pharmaceutical composition of antihypertriglyceridemic activity containing benzoxazepine derivatives

Pharmaceutical composition of antihypertriglyceridemic activity containing benzoxazepine derivatives Download PDF

Info

Publication number: HUT73422A
Authority: HU; Hungary
Prior art keywords: optionally substituted; group; antihypertriglyceridemic; composition; optionally
Prior art date: 1994-10-07

Application number

HU9502918A

Other languages

English (en)

Hungarian (hu)

Other versions

HU9502918D0 (en

Inventor

Yasuo Sugiyama

Hidefumi Yukimasa

Original Assignee

Takeda Chemical Industries Ltd

Priority date

1994-10-07

Filing date

1995-10-05

Publication date

1996-07-29

1995-10-05 Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd

1995-11-28 Publication of HU9502918D0 publication Critical patent/HU9502918D0/hu

1996-07-29 Publication of HUT73422A publication Critical patent/HUT73422A/hu

Links

230000001346 anti-hypertriglyceridemic effect Effects 0.000 title claims abstract description 40
239000008194 pharmaceutical composition Substances 0.000 title description 3
ZCXLTWVZYXBHJS-UHFFFAOYSA-N 1,2-benzoxazepine Chemical class O1N=CC=CC2=CC=CC=C12 ZCXLTWVZYXBHJS-UHFFFAOYSA-N 0.000 title 1
125000001424 substituent group Chemical group 0.000 claims abstract description 86
150000001875 compounds Chemical class 0.000 claims abstract description 65
239000000203 mixture Substances 0.000 claims abstract description 60
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 38
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 26
238000011282 treatment Methods 0.000 claims abstract description 26
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 25
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 25
125000003277 amino group Chemical group 0.000 claims abstract description 24
125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 24
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 23
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 20
150000003839 salts Chemical class 0.000 claims abstract description 19
125000005842 heteroatom Chemical group 0.000 claims abstract description 11
208000006575 hypertriglyceridemia Diseases 0.000 claims abstract description 10
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 6
-1 2,4-dimethoxyphenyl Chemical group 0.000 claims description 158
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 97
125000000217 alkyl group Chemical group 0.000 claims description 49
229910052739 hydrogen Inorganic materials 0.000 claims description 20
239000001257 hydrogen Substances 0.000 claims description 20
208000031226 Hyperlipidaemia Diseases 0.000 claims description 17
WHLFSPLJCRQWJQ-UHFFFAOYSA-N 2-(oxazepin-3-yl)acetic acid Chemical compound OC(=O)CC1=NOC=CC=C1 WHLFSPLJCRQWJQ-UHFFFAOYSA-N 0.000 claims description 15
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 12
230000002265 prevention Effects 0.000 claims description 12
238000000034 method Methods 0.000 claims description 11
125000002947 alkylene group Chemical group 0.000 claims description 10
125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
150000001555 benzenes Chemical group 0.000 claims description 7
159000000000 sodium salts Chemical group 0.000 claims description 6
125000004122 cyclic group Chemical group 0.000 claims description 4
239000000546 pharmaceutical excipient Substances 0.000 claims description 4
125000000547 substituted alkyl group Chemical group 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims 5
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 1
239000003937 drug carrier Substances 0.000 claims 1
239000008024 pharmaceutical diluent Substances 0.000 claims 1
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 abstract description 19
230000000694 effects Effects 0.000 abstract description 6
201000005577 familial hyperlipidemia Diseases 0.000 abstract description 5
239000000470 constituent Substances 0.000 abstract 1
238000011321 prophylaxis Methods 0.000 abstract 1
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 description 50
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 29
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 27
239000003826 tablet Substances 0.000 description 25
235000012000 cholesterol Nutrition 0.000 description 23
125000003118 aryl group Chemical group 0.000 description 21
229910052801 chlorine Inorganic materials 0.000 description 19
239000008187 granular material Substances 0.000 description 19
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 19
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
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 16
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 16
229910052794 bromium Inorganic materials 0.000 description 16
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 15
125000003710 aryl alkyl group Chemical group 0.000 description 15
239000002775 capsule Substances 0.000 description 15
239000000460 chlorine Chemical group 0.000 description 15
229910052731 fluorine Inorganic materials 0.000 description 15
239000011737 fluorine Substances 0.000 description 15
235000019359 magnesium stearate Nutrition 0.000 description 15
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 14
229910052736 halogen Inorganic materials 0.000 description 14
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 13
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
239000008101 lactose Substances 0.000 description 13
229940016286 microcrystalline cellulose Drugs 0.000 description 13
235000019813 microcrystalline cellulose Nutrition 0.000 description 13
239000008108 microcrystalline cellulose Substances 0.000 description 13
239000011734 sodium Substances 0.000 description 13
229910052708 sodium Inorganic materials 0.000 description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
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
239000004480 active ingredient Substances 0.000 description 12
125000003545 alkoxy group Chemical group 0.000 description 12
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
150000002367 halogens Chemical class 0.000 description 12
125000002252 acyl group Chemical group 0.000 description 11
125000004432 carbon atom Chemical group C* 0.000 description 11
229910052757 nitrogen Inorganic materials 0.000 description 11
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
201000010099 disease Diseases 0.000 description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
239000007924 injection Substances 0.000 description 10
238000002347 injection Methods 0.000 description 10
229910052740 iodine Inorganic materials 0.000 description 10
229910052760 oxygen Inorganic materials 0.000 description 10
239000001301 oxygen Substances 0.000 description 10
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
229920002261 Corn starch Polymers 0.000 description 9
239000002552 dosage form Substances 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
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 8
125000004429 atom Chemical group 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
125000000392 cycloalkenyl group Chemical group 0.000 description 8
125000005843 halogen group Chemical group 0.000 description 8
239000011630 iodine Substances 0.000 description 8
239000000243 solution Substances 0.000 description 8
238000012360 testing method Methods 0.000 description 8
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
108010010234 HDL Lipoproteins Proteins 0.000 description 7
102000015779 HDL Lipoproteins Human genes 0.000 description 7
235000019759 Maize starch Nutrition 0.000 description 7
229910052799 carbon Inorganic materials 0.000 description 7
125000001309 chloro group Chemical group Cl* 0.000 description 7
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 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
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 7
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 7
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
239000000126 substance Substances 0.000 description 7
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 6
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
239000003708 ampul Substances 0.000 description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
125000000753 cycloalkyl group Chemical group 0.000 description 6
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
239000003112 inhibitor Substances 0.000 description 6
150000002632 lipids Chemical class 0.000 description 6
229910052717 sulfur Inorganic materials 0.000 description 6
239000011593 sulfur Chemical group 0.000 description 6
125000001544 thienyl group Chemical group 0.000 description 6
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 5
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 5
108010062497 VLDL Lipoproteins Proteins 0.000 description 5
210000004369 blood Anatomy 0.000 description 5
239000008280 blood Substances 0.000 description 5
125000002541 furyl group Chemical group 0.000 description 5
239000007903 gelatin capsule Substances 0.000 description 5
125000001041 indolyl group Chemical group 0.000 description 5
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
125000004433 nitrogen atom Chemical group N* 0.000 description 5
125000004043 oxo group Chemical group O=* 0.000 description 5
125000004076 pyridyl group Chemical group 0.000 description 5
239000000725 suspension Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
125000006273 (C1-C3) alkyl group Chemical group 0.000 description 4
241000700159 Rattus Species 0.000 description 4
208000007536 Thrombosis Diseases 0.000 description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
125000002723 alicyclic group Chemical group 0.000 description 4
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
125000001589 carboacyl group Chemical group 0.000 description 4
235000014113 dietary fatty acids Nutrition 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
229960002768 dipyridamole Drugs 0.000 description 4
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
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 4
239000000194 fatty acid Substances 0.000 description 4
229930195729 fatty acid Natural products 0.000 description 4
150000004665 fatty acids Chemical class 0.000 description 4
125000001153 fluoro group Chemical group F* 0.000 description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
125000002883 imidazolyl group Chemical group 0.000 description 4
235000010355 mannitol Nutrition 0.000 description 4
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
239000003755 preservative agent Substances 0.000 description 4
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 4
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 4
125000003373 pyrazinyl group Chemical group 0.000 description 4
125000000714 pyrimidinyl group Chemical group 0.000 description 4
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
125000003396 thiol group Chemical class [H]S* 0.000 description 4
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
241000282693 Cercopithecidae Species 0.000 description 3
229920002785 Croscarmellose sodium Polymers 0.000 description 3
108010007622 LDL Lipoproteins Proteins 0.000 description 3
102000007330 LDL Lipoproteins Human genes 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
206010029164 Nephrotic syndrome Diseases 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 3
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 3
239000000654 additive Substances 0.000 description 3
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
239000007864 aqueous solution Substances 0.000 description 3
235000019445 benzyl alcohol Nutrition 0.000 description 3
125000001246 bromo group Chemical group Br* 0.000 description 3
150000001721 carbon 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
230000000875 corresponding effect Effects 0.000 description 3
229960001681 croscarmellose sodium Drugs 0.000 description 3
235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 3
125000004093 cyano group Chemical group *C#N 0.000 description 3
125000001485 cycloalkadienyl group Chemical group 0.000 description 3
206010012601 diabetes mellitus Diseases 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
239000003814 drug Substances 0.000 description 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
238000001802 infusion Methods 0.000 description 3
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