AU659691B2 - Pharmaceutical compositions for oral use and method of preparing them - Google Patents
Pharmaceutical compositions for oral use and method of preparing them Download PDFInfo
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- AU659691B2 AU659691B2 AU28391/92A AU2839192A AU659691B2 AU 659691 B2 AU659691 B2 AU 659691B2 AU 28391/92 A AU28391/92 A AU 28391/92A AU 2839192 A AU2839192 A AU 2839192A AU 659691 B2 AU659691 B2 AU 659691B2
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- 238000000034 method Methods 0.000 title claims abstract description 34
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 19
- 239000000203 mixture Substances 0.000 claims abstract description 69
- 150000001875 compounds Chemical class 0.000 claims abstract description 60
- 239000000126 substance Substances 0.000 claims abstract description 58
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 45
- 238000002844 melting Methods 0.000 claims abstract description 28
- 230000008018 melting Effects 0.000 claims abstract description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 21
- 150000001450 anions Chemical class 0.000 claims abstract description 16
- 102000005862 Angiotensin II Human genes 0.000 claims abstract description 15
- 101800000733 Angiotensin-2 Proteins 0.000 claims abstract description 15
- 229950006323 angiotensin ii Drugs 0.000 claims abstract description 15
- CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 claims abstract description 14
- 230000003042 antagnostic effect Effects 0.000 claims abstract description 13
- 238000000465 moulding Methods 0.000 claims abstract description 12
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 10
- 125000006850 spacer group Chemical group 0.000 claims abstract 2
- -1 fatty acid ester Chemical class 0.000 claims description 91
- 229910052799 carbon Inorganic materials 0.000 claims description 45
- 150000001721 carbon Chemical class 0.000 claims description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 36
- 125000005842 heteroatom Chemical class 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 26
- 239000000194 fatty acid Substances 0.000 claims description 26
- 229930195729 fatty acid Natural products 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000002947 alkylene group Chemical group 0.000 claims description 16
- 150000005846 sugar alcohols Polymers 0.000 claims description 14
- 229920000642 polymer Polymers 0.000 claims description 13
- 150000002430 hydrocarbons Chemical class 0.000 claims description 12
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 12
- 229910052757 nitrogen Chemical class 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 150000004665 fatty acids Chemical class 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical group 0.000 claims description 10
- 125000004433 nitrogen atom Chemical class N* 0.000 claims description 10
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 10
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 8
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- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 6
- FLOKGHWIQFCIJW-UHFFFAOYSA-N 2-butyl-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylic acid Chemical compound CCCCC1=NC2=CC=CC(C(O)=O)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 FLOKGHWIQFCIJW-UHFFFAOYSA-N 0.000 claims 2
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims 2
- NQZDOSXQAGAIAB-UHFFFAOYSA-N 2-cyclohexyloxycarbonyloxyethyl 2-ethoxy-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylate Chemical compound C=12N(CC=3C=CC(=CC=3)C=3C(=CC=CC=3)C=3NN=NN=3)C(OCC)=NC2=CC=CC=1C(=O)OCCOC(=O)OC1CCCCC1 NQZDOSXQAGAIAB-UHFFFAOYSA-N 0.000 claims 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 22
- 238000009472 formulation Methods 0.000 description 12
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 11
- 125000002252 acyl group Chemical group 0.000 description 11
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 11
- 229940093429 polyethylene glycol 6000 Drugs 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 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 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 239000008187 granular material Substances 0.000 description 8
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 8
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 8
- 239000008101 lactose Substances 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 239000000600 sorbitol Substances 0.000 description 8
- VVQNAFBGAWCMLU-UHFFFAOYSA-N 1h-benzimidazole-4-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=C1N=CN2 VVQNAFBGAWCMLU-UHFFFAOYSA-N 0.000 description 7
- 229920002261 Corn starch Polymers 0.000 description 7
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 7
- 229930006000 Sucrose Natural products 0.000 description 7
- 239000008120 corn starch Substances 0.000 description 7
- 238000001727 in vivo Methods 0.000 description 7
- 229920001451 polypropylene glycol Polymers 0.000 description 7
- 239000005720 sucrose Substances 0.000 description 7
- 206010020772 Hypertension Diseases 0.000 description 6
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 235000019359 magnesium stearate Nutrition 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000013112 stability test Methods 0.000 description 6
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 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 5
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 4
- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 239000008116 calcium stearate Substances 0.000 description 4
- 235000013539 calcium stearate Nutrition 0.000 description 4
- 229960000541 cetyl alcohol Drugs 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 4
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 4
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 4
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 4
- KAKQVSNHTBLJCH-UHFFFAOYSA-N trifluoromethanesulfonimidic acid Chemical compound NS(=O)(=O)C(F)(F)F KAKQVSNHTBLJCH-UHFFFAOYSA-N 0.000 description 4
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 3
- 239000005541 ACE inhibitor Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
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- 238000006243 chemical reaction Methods 0.000 description 3
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- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 3
- 238000004898 kneading Methods 0.000 description 3
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- 229940055577 oleyl alcohol Drugs 0.000 description 3
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 3
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- ZMPAPJBFYQSNFM-UHFFFAOYSA-N 1-sulfanylimidazole Chemical compound SN1C=CN=C1 ZMPAPJBFYQSNFM-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- YQEMORVAKMFKLG-UHFFFAOYSA-N 2-stearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
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- XQKRPEDJRVOOAA-UHFFFAOYSA-J [Mg+2].[Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O Chemical compound [Mg+2].[Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XQKRPEDJRVOOAA-UHFFFAOYSA-J 0.000 description 2
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- 125000003302 alkenyloxy group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
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- 229910052794 bromium Inorganic materials 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
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- 125000004093 cyano group Chemical group *C#N 0.000 description 2
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- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
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- HOWGUJZVBDQJKV-UHFFFAOYSA-N docosane Chemical compound CCCCCCCCCCCCCCCCCCCCCC HOWGUJZVBDQJKV-UHFFFAOYSA-N 0.000 description 2
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- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- LQERIDTXQFOHKA-UHFFFAOYSA-N nonadecane Chemical compound CCCCCCCCCCCCCCCCCCC LQERIDTXQFOHKA-UHFFFAOYSA-N 0.000 description 2
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
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- 235000019271 petrolatum Nutrition 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
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- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
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- 150000003839 salts Chemical class 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/2031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Cardiology (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30492491 | 1991-11-20 | ||
| JP3-304924 | 1991-11-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2839192A AU2839192A (en) | 1993-05-27 |
| AU659691B2 true AU659691B2 (en) | 1995-05-25 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU28391/92A Expired AU659691B2 (en) | 1991-11-20 | 1992-11-13 | Pharmaceutical compositions for oral use and method of preparing them |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5534534A (enExample) |
| EP (3) | EP0782852B1 (enExample) |
| KR (1) | KR100256633B1 (enExample) |
| CN (1) | CN1047518C (enExample) |
| AT (2) | ATE157248T1 (enExample) |
| AU (1) | AU659691B2 (enExample) |
| BR (1) | BR1100336A (enExample) |
| CA (1) | CA2083305C (enExample) |
| DE (2) | DE69233424T2 (enExample) |
| DK (1) | DK0546358T3 (enExample) |
| ES (1) | ES2104797T3 (enExample) |
| FI (2) | FI111604B (enExample) |
| GR (1) | GR3025338T3 (enExample) |
| HU (1) | HU211608A9 (enExample) |
| MX (1) | MX9206634A (enExample) |
| NO (1) | NO304408B1 (enExample) |
| NZ (1) | NZ245175A (enExample) |
| TW (1) | TW284688B (enExample) |
Families Citing this family (51)
| Publication number | Priority date | Publication date | Assignee | Title |
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| TW284688B (enExample) * | 1991-11-20 | 1996-09-01 | Takeda Pharm Industry Co Ltd | |
| TW272942B (enExample) * | 1993-02-10 | 1996-03-21 | Takeda Pharm Industry Co Ltd | |
| CA2125251C (en) * | 1993-06-07 | 2005-04-26 | Yoshiyuki Inada | A pharmaceutical composition for angiotensin ii-mediated diseases |
| US5753672A (en) * | 1994-04-19 | 1998-05-19 | Tanabe Seiyaku Co., Ltd. | Imidazopyridine derivatives and process for preparing the same |
| AU679616B2 (en) * | 1994-04-19 | 1997-07-03 | Tanabe Seiyaku Co., Ltd. | Imidazopyridine derivatives and process for preparing the same |
| TW418204B (en) * | 1997-03-28 | 2001-01-11 | Dev Center Biotechnology | Novel 1,2,4-triazine-5-ketonyl benzene derivatives and the analogs, the preparation, and the pharmaceutical compositions as angiotension II receptor antogonists |
| US6297239B1 (en) | 1997-10-08 | 2001-10-02 | Merck & Co., Inc. | Inhibitors of prenyl-protein transferase |
| IL137979A0 (en) * | 1998-03-04 | 2001-10-31 | Takeda Chemical Industries Ltd | Production, release preparation for aii antagonist-sustained and use thereof |
| US7115644B2 (en) * | 2002-09-13 | 2006-10-03 | Boehringer Ingelheim Pharmaceuticals Inc. | Heterocyclic compounds |
| US20050031683A1 (en) * | 2003-08-04 | 2005-02-10 | Ashish Kapoor | Solid pharmaceutical composition |
| ES2284068T3 (es) * | 2003-10-16 | 2007-11-01 | Teva Pharmaceutical Industries Limited | Preparacion de candesartan cilexetilo. |
| US20050175689A1 (en) * | 2003-10-27 | 2005-08-11 | Yamanouchi Pharmaceutical Co., Ltd. | Coated fine particles containing drug for intrabuccally fast disintegrating tablet |
| WO2005070398A2 (en) * | 2004-01-23 | 2005-08-04 | Ranbaxy Laboratories Limited | Pharmaceutical compositions of candesartan cilexetil stabilized with co-solvents |
| EP1711168A2 (en) * | 2004-01-23 | 2006-10-18 | Ranbaxy Laboratories Limited | Oral pharmaceutical compositions of candesartan cilexetil |
| EP1713795A2 (en) * | 2004-02-11 | 2006-10-25 | Teva Pharmaceutical Industries Ltd. | Candesartan cilexetil polymorphs |
| WO2005084670A1 (en) | 2004-03-01 | 2005-09-15 | Lek Pharmaceuticals D.D. | Pharmaceutical formulation |
| CZ23088U1 (cs) * | 2004-03-25 | 2011-12-19 | Astellas Pharma Inc. | Kompozice pevného farmaceutického prípravku solifenacinu nebo jeho soli |
| KR100908308B1 (ko) * | 2004-05-05 | 2009-07-17 | 테바 파마슈티컬 인더스트리즈 리미티드 | 순도가 높은 칸데사르탄 실렉세틸의 제조 |
| US7588779B2 (en) * | 2004-05-28 | 2009-09-15 | Andrx Labs, Llc | Pharmaceutical formulation containing a biguanide and an angiotensin antagonist |
| CA2591761A1 (en) * | 2004-12-27 | 2006-07-06 | Astellas Pharma Inc. | Stable particulate pharmaceutical composition of solifenacin or salt thereof |
| EP1835890A2 (en) * | 2005-01-06 | 2007-09-26 | Elan Pharma International Limited | Nanoparticulate candesartan formulations |
| US20060194858A1 (en) * | 2005-01-14 | 2006-08-31 | Omer Malachi | Preparation of crude candesartan cilexetil |
| WO2006079496A1 (en) * | 2005-01-26 | 2006-08-03 | Lek Pharmaceuticals D.D. | New pharmaceutical composition containing candesartan cilexetil as lipophilic crystalline substance |
| WO2006122254A2 (en) * | 2005-05-10 | 2006-11-16 | Teva Pharmaceutical Industries Ltd. | Stable micronized candesartan cilexetil and methods for preparing thereof |
| US7815939B2 (en) * | 2005-07-20 | 2010-10-19 | Astellas Pharma Inc. | Coated fine particles containing drug for intrabuccally fast disintegrating dosage forms |
| WO2007126135A1 (en) * | 2006-04-27 | 2007-11-08 | Takeda Pharmaceutical Company Limited | Pharmaceutical composition of angiotensin ii antagonists with pioglitazone hcl |
| GEP20125420B (en) * | 2006-08-10 | 2012-03-26 | Takeda Pharmaceutical | Solid pharmaceutical composition comprising benzimidazole compound |
| WO2008045006A1 (en) * | 2006-10-11 | 2008-04-17 | Fako Ilaclari A. S. | Formulations of candesartan |
| ES2301401B1 (es) * | 2006-11-28 | 2009-06-08 | Laboratorios Liconsa S.A. | Composicion farmaceutica solida estabilizada de candesartan cilexetilo. |
| EP1952806A1 (en) | 2007-02-01 | 2008-08-06 | Helm AG | Process for the preparation of adsorbates of candesartan |
| ES2351542T3 (es) * | 2007-03-08 | 2011-02-07 | Teva Pharmaceutical Industries Ltd. | Composición farmacéutica que comprende candesartan cilexetilo. |
| PE20130210A1 (es) * | 2007-03-28 | 2013-03-11 | Takeda Pharmaceutical | Composicion farmaceutica solida que comprende un derivado de bencimidazol y un agente de control de ph |
| JP5139515B2 (ja) | 2007-04-25 | 2013-02-06 | テバ ファーマシューティカル インダストリーズ リミティド | 医薬賦形剤複合体 |
| WO2008149338A2 (en) * | 2007-06-06 | 2008-12-11 | Dexcel Ltd. | Process for forming solid oral dosage forms of angiotensin ii receptor antagonists |
| DE102007052070A1 (de) | 2007-10-30 | 2009-05-07 | Tiefenbacher Pharmachemikalien Alfred E. Tiefenbacher Gmbh & Co. Kg | Candesartancilexetil |
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- 1992-11-20 KR KR1019920021902A patent/KR100256633B1/ko not_active Expired - Lifetime
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| SU1653780A1 (ru) * | 1988-07-25 | 1991-06-07 | Piskov Vyacheslav B | Способ получени жидкой формы антгельминтика из группы бензимидазолов с использованием органического растворител |
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