FI90393B - Förfarande för framställning av en oral farmaceutisk beredning som är stabil mot missfärgning - Google Patents
Förfarande för framställning av en oral farmaceutisk beredning som är stabil mot missfärgning Download PDFInfo
- Publication number
- FI90393B FI90393B FI871913A FI871913A FI90393B FI 90393 B FI90393 B FI 90393B FI 871913 A FI871913 A FI 871913A FI 871913 A FI871913 A FI 871913A FI 90393 B FI90393 B FI 90393B
- Authority
- FI
- Finland
- Prior art keywords
- omeprazole
- alkaline
- pills
- process according
- magnesium
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 30
- 238000002845 discoloration Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title description 55
- 239000008203 oral pharmaceutical composition Substances 0.000 title 1
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 claims description 181
- 229960000381 omeprazole Drugs 0.000 claims description 179
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 55
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 54
- 239000010410 layer Substances 0.000 claims description 50
- 239000002552 dosage form Substances 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 37
- 239000002702 enteric coating Substances 0.000 claims description 35
- 238000009505 enteric coating Methods 0.000 claims description 35
- 238000000576 coating method Methods 0.000 claims description 32
- 239000000395 magnesium oxide Substances 0.000 claims description 29
- 239000011248 coating agent Substances 0.000 claims description 26
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 23
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 23
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 23
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 18
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 16
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 16
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 16
- 239000004480 active ingredient Substances 0.000 claims description 15
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 15
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 15
- 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 claims description 15
- 239000000126 substance Substances 0.000 claims description 15
- 239000011777 magnesium Substances 0.000 claims description 14
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 12
- 229910052749 magnesium Inorganic materials 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 10
- 239000000347 magnesium hydroxide Substances 0.000 claims description 10
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 10
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 claims description 9
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 claims description 9
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 9
- 239000011734 sodium Substances 0.000 claims description 9
- 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 claims description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 8
- 239000011575 calcium Substances 0.000 claims description 8
- 229910052791 calcium Inorganic materials 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- 229920000623 Cellulose acetate phthalate Polymers 0.000 claims description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 7
- 229910052782 aluminium Inorganic materials 0.000 claims description 7
- 239000011591 potassium Substances 0.000 claims description 7
- 229910052700 potassium Inorganic materials 0.000 claims description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 6
- 229940081734 cellulose acetate phthalate Drugs 0.000 claims description 6
- 159000000011 group IA salts Chemical class 0.000 claims description 6
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
- 239000002131 composite material Substances 0.000 claims description 4
- 239000008183 oral pharmaceutical preparation Substances 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 239000011324 bead Substances 0.000 claims description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
- 239000001095 magnesium carbonate Substances 0.000 claims description 2
- 229910000021 magnesium carbonate Inorganic materials 0.000 claims description 2
- 229940100467 polyvinyl acetate phthalate Drugs 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- PPQREHKVAOVYBT-UHFFFAOYSA-H aluminium carbonate Inorganic materials [Al+3].[Al+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O PPQREHKVAOVYBT-UHFFFAOYSA-H 0.000 claims 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 235000011082 potassium citrates Nutrition 0.000 claims 1
- 235000011009 potassium phosphates Nutrition 0.000 claims 1
- 239000008188 pellet Substances 0.000 description 82
- 239000000203 mixture Substances 0.000 description 80
- 239000006187 pill Substances 0.000 description 80
- 238000009472 formulation Methods 0.000 description 54
- 239000011162 core material Substances 0.000 description 52
- 239000003826 tablet Substances 0.000 description 49
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 42
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 235000019441 ethanol Nutrition 0.000 description 24
- 229920000642 polymer Polymers 0.000 description 23
- 238000003860 storage Methods 0.000 description 23
- 229960000541 cetyl alcohol Drugs 0.000 description 22
- 239000000843 powder Substances 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- 239000012153 distilled water Substances 0.000 description 19
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 230000002496 gastric effect Effects 0.000 description 13
- 239000000725 suspension Substances 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 12
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 12
- 239000002775 capsule Substances 0.000 description 12
- 239000003814 drug Substances 0.000 description 12
- 239000007903 gelatin capsule Substances 0.000 description 12
- 239000008101 lactose Substances 0.000 description 12
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 11
- 229940079593 drug Drugs 0.000 description 11
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 239000012530 fluid Substances 0.000 description 10
- 230000000968 intestinal effect Effects 0.000 description 10
- 230000007935 neutral effect Effects 0.000 description 10
- GUBGYTABKSRVRQ-DCSYEGIMSA-N Beta-Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-DCSYEGIMSA-N 0.000 description 9
- 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 9
- 229930195725 Mannitol Natural products 0.000 description 9
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 9
- -1 hydrogen ions Chemical class 0.000 description 9
- 239000000594 mannitol Substances 0.000 description 9
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- 229940016286 microcrystalline cellulose Drugs 0.000 description 9
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 9
- 239000008108 microcrystalline cellulose Substances 0.000 description 9
- 239000006174 pH buffer Substances 0.000 description 9
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- 210000000813 small intestine Anatomy 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 235000012254 magnesium hydroxide Nutrition 0.000 description 8
- 159000000003 magnesium salts Chemical class 0.000 description 8
- 235000019359 magnesium stearate Nutrition 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 230000036470 plasma concentration Effects 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- 159000000000 sodium salts Chemical class 0.000 description 8
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 8
- 230000033228 biological regulation Effects 0.000 description 7
- 229910000397 disodium phosphate Inorganic materials 0.000 description 7
- 235000019800 disodium phosphate Nutrition 0.000 description 7
- 238000004090 dissolution Methods 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- 230000007774 longterm Effects 0.000 description 7
- 239000008194 pharmaceutical composition Substances 0.000 description 7
- 239000004141 Sodium laurylsulphate Substances 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- 230000015556 catabolic process Effects 0.000 description 6
- 229920001688 coating polymer Polymers 0.000 description 6
- 238000006731 degradation reaction Methods 0.000 description 6
- 238000009792 diffusion process Methods 0.000 description 6
- 239000006186 oral dosage form Substances 0.000 description 6
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- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 230000028327 secretion Effects 0.000 description 6
- 239000001488 sodium phosphate Substances 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
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- 239000007788 liquid Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- RYXPMWYHEBGTRV-UHFFFAOYSA-N Omeprazole sodium Chemical compound [Na+].N=1C2=CC(OC)=CC=C2[N-]C=1S(=O)CC1=NC=C(C)C(OC)=C1C RYXPMWYHEBGTRV-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 4
- 230000003139 buffering effect Effects 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
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- 235000013773 glyceryl triacetate Nutrition 0.000 description 4
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- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 210000000936 intestine Anatomy 0.000 description 4
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- 210000002784 stomach Anatomy 0.000 description 4
- 229960002622 triacetin Drugs 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- 229920003135 Eudragit® L 100-55 Polymers 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical class [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- 238000004061 bleaching Methods 0.000 description 3
- 239000007853 buffer solution Substances 0.000 description 3
- 239000000920 calcium hydroxide Substances 0.000 description 3
- 235000011116 calcium hydroxide Nutrition 0.000 description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 3
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- 239000011247 coating layer Substances 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000002662 enteric coated tablet Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- HQPMKSGTIOYHJT-UHFFFAOYSA-N ethane-1,2-diol;propane-1,2-diol Chemical compound OCCO.CC(O)CO HQPMKSGTIOYHJT-UHFFFAOYSA-N 0.000 description 3
- 210000004211 gastric acid Anatomy 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
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- 230000006641 stabilisation Effects 0.000 description 3
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- 230000000087 stabilizing effect Effects 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
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- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 2
- 229920003139 Eudragit® L 100 Polymers 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
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- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
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- 230000001143 conditioned effect Effects 0.000 description 2
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- 238000000354 decomposition reaction Methods 0.000 description 2
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 2
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- FYFFGSSZFBZTAH-UHFFFAOYSA-N methylaminomethanetriol Chemical compound CNC(O)(O)O FYFFGSSZFBZTAH-UHFFFAOYSA-N 0.000 description 2
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- 229910000403 monosodium phosphate Inorganic materials 0.000 description 2
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- 230000003389 potentiating effect Effects 0.000 description 2
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- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 2
- RRFCKCAQHRITRG-UHFFFAOYSA-N sodium;5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]benzimidazol-3-ide;hydrate Chemical compound O.[Na+].N=1C2=CC(OC)=CC=C2[N-]C=1S(=O)CC1=NC=C(C)C(OC)=C1C RRFCKCAQHRITRG-UHFFFAOYSA-N 0.000 description 2
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- 206010002368 Anger Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 101100283604 Caenorhabditis elegans pigk-1 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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- YUXIBTJKHLUKBD-UHFFFAOYSA-N Dibutyl succinate Chemical compound CCCCOC(=O)CCC(=O)OCCCC YUXIBTJKHLUKBD-UHFFFAOYSA-N 0.000 description 1
- 101100326341 Drosophila melanogaster brun gene Proteins 0.000 description 1
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- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- GAMPNQJDUFQVQO-UHFFFAOYSA-N acetic acid;phthalic acid Chemical compound CC(O)=O.OC(=O)C1=CC=CC=C1C(O)=O GAMPNQJDUFQVQO-UHFFFAOYSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
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- 150000001447 alkali salts Chemical class 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
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- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
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- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
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- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
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- 238000003818 flash chromatography Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 230000027119 gastric acid secretion Effects 0.000 description 1
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- 239000008273 gelatin Substances 0.000 description 1
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- 229910052739 hydrogen Inorganic materials 0.000 description 1
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- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
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- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- 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
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
-
- 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
- A61K31/435—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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1611—Inorganic compounds
-
- 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
- A61K9/2009—Inorganic compounds
-
- 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
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2886—Dragees; Coated pills or tablets, e.g. with film or compression coating having two or more different drug-free coatings; Tablets of the type inert core-drug layer-inactive layer
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5073—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Claims (9)
1. Förfarande för framstäilning av en oral, farmaceutisk be-redning som är stabil mot missfärgning och som innehäller omeprazol som den aktiva ingrediensen, kännetecknat av att omeprazol blandad med en aikaiiskt reagerande förening, el-ler ett alkaliskt sait av omeprazol eventuellt blandat med en alkaliskt reagerande förening, formas till kärnor och dessa kärnor, vilka är i form av smä pärlor eller tabletter, drageras med ett eller flera inert reagerande underskyddande drageringsskikt innehällande tablettfyllnadsmedel, vilka är lösliga eller snabbt sönderfallande i vatten eller polymera, vattenlösliga, filmbildande föreningar eventuellt innehällande pH-buffrande alkaliska föreningar mellan den alkaliskt reagerande kärnan och ett yttre skikt, som är ett magsaft-resistent drageringsskikt, varefter de underskyddsdragerade kärnorna drageras ytterligare med nämnda yttre magsaftresis-tenta drageringsskikt.
2. Förfarande enligt patentkravet 1, kännetecknat av att den använda underskyddande drageringen innehäller hydroxi-propylmetylcellulosa, hydroxipropylcellulosa eller poly-vinylpyrrolidon.
3. Förfarande enligt patentkravet 1, kännetecknat av att den använda underskyddande drageringen innefattar tvä eller flera underskikt och att det inre underskiktet innehäller en eller flera av magnesiumoxid, magnesiumhydroxid eller kom-positsubstans AI203 · 6MgO · C02· 121^0 eller MgO· A1203· 2Si02-nH20, väri n inte är ett heltal och mindre än 2.
4. Förfarande enligt patentkravet 1, kännetecknat av att omeprazol är blandad med pH-buffrande aikaiisk förening, vilken ger omeprazolens mikroomgivning ett pH av 7-12 för bildande av den alkaliska kärnan.
5. Förfarande enligt patentkravet 4, kännetecknat av att den alkaliska föreningen med vilken omeprazol är blandad innefattar en eller flera av magnesiumoxid, -hydroxid el- si 90395 ler -karbonat, aluminiumhydroxid, aluminium-, kalcium-, natrium- eller kaliumkarbonat, -fosfat eller -citrat, alu-minium/magnesiumkompositföreningarna Α1203· 6Mg0-C02· 12H20 eller Mg0-Al203-Si02-nH20, där n inte är ett heltal och mindre an 2 .
6. Förfarande enligt patentkravet 1, kännetecknat av att ett alkaliskt salt av omeprazol, säsom natrium-, kalium-, magnesium-, kalcium- eller ammoniumsaltet, är bildat och inkluderat i den alkaliska kärnan.
7. Förfarande enligt patentkravet 6, kannetecknat av att det alkaliska saltet av omeprazol är blandat med en aikaiisk förening för bildande av den alkaliska kärnan.
8. Förfarande enligt patentkravet 1, kannetecknat av att man använder en magsaftsresistent dragering innefattande hydroxipropylmetylcellulosaftaiat, cellulosaacetatftaiat, sampolymeriserad metakrylsyra/metakrylsyrametylester eller polyvinylacetatftaiat, eventuellt innehällande en mjukgöra-re.
9. Förfarande enligt patentkravet 1, kännetecknat av att man framställer en omeprazolinnehällande doseringsform, vars vatteninnehäll inte överstiger 1,5 vikts-%.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8610572 | 1986-04-30 | ||
| GB08610572A GB2189698A (en) | 1986-04-30 | 1986-04-30 | Coated omeprazole tablets |
| SG154294A SG154294G (en) | 1986-04-30 | 1994-10-21 | New pharmaceutical preparation for oral use |
| SG154294 | 1994-10-21 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI871913A0 FI871913A0 (sv) | 1987-04-29 |
| FI871913L FI871913L (sv) | 1987-10-31 |
| FI90393B true FI90393B (sv) | 1993-10-29 |
| FI90393C FI90393C (sv) | 1994-02-10 |
Family
ID=26290693
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI871913A FI90393C (sv) | 1986-04-30 | 1987-04-29 | Förfarande för framställning av en oral farmaceutisk beredning som är stabil mot missfärgning |
Country Status (35)
| Country | Link |
|---|---|
| US (1) | US4786505A (sv) |
| EP (3) | EP0567201B1 (sv) |
| JP (2) | JPS62258320A (sv) |
| KR (1) | KR910004579B1 (sv) |
| CN (1) | CN1020852C (sv) |
| AR (1) | AR240250A1 (sv) |
| AT (3) | ATE140387T1 (sv) |
| CA (1) | CA1292693C (sv) |
| CY (1) | CY1810A (sv) |
| DD (1) | DD273197A5 (sv) |
| DE (3) | DE3751860T2 (sv) |
| DK (1) | DK169988B1 (sv) |
| DZ (1) | DZ1077A1 (sv) |
| ES (3) | ES2135443T3 (sv) |
| FI (1) | FI90393C (sv) |
| GB (1) | GB2189698A (sv) |
| GR (4) | GR890300058T1 (sv) |
| HK (2) | HK135294A (sv) |
| HR (1) | HRP920854B1 (sv) |
| HU (1) | HU196708B (sv) |
| IE (1) | IE61416B1 (sv) |
| IL (1) | IL82911A (sv) |
| IS (1) | IS1917B (sv) |
| LT (1) | LT3699B (sv) |
| LV (2) | LV10357B (sv) |
| NO (1) | NO174239C (sv) |
| NZ (1) | NZ220096A (sv) |
| PH (1) | PH25701A (sv) |
| PL (1) | PL151631B1 (sv) |
| PT (1) | PT84785B (sv) |
| RU (2) | RU1820837C (sv) |
| SG (1) | SG154294G (sv) |
| SI (1) | SI8710681A8 (sv) |
| YU (1) | YU46192B (sv) |
| ZA (1) | ZA872378B (sv) |
Families Citing this family (366)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5433959A (en) * | 1986-02-13 | 1995-07-18 | Takeda Chemical Industries, Ltd. | Stabilized pharmaceutical composition |
| US6749864B2 (en) | 1986-02-13 | 2004-06-15 | Takeda Chemical Industries, Ltd. | Stabilized pharmaceutical composition |
| GB2189699A (en) * | 1986-04-30 | 1987-11-04 | Haessle Ab | Coated acid-labile medicaments |
| US5026560A (en) * | 1987-01-29 | 1991-06-25 | Takeda Chemical Industries, Ltd. | Spherical granules having core and their production |
| GB8724763D0 (en) * | 1987-10-22 | 1987-11-25 | Aps Research Ltd | Sustained-release formulations |
| US5160743A (en) * | 1988-04-28 | 1992-11-03 | Alza Corporation | Annealed composition for pharmaceutically acceptable drug |
| US5006346A (en) * | 1988-04-28 | 1991-04-09 | Alza Corporation | Delivery system |
| JPH0768125B2 (ja) * | 1988-05-18 | 1995-07-26 | エーザイ株式会社 | 酸不安定化合物の内服用製剤 |
| JPH0737383B2 (ja) * | 1988-07-11 | 1995-04-26 | エーザイ株式会社 | 胃酸分泌抑制剤含有固型製剤 |
| US5202128A (en) * | 1989-01-06 | 1993-04-13 | F. H. Faulding & Co. Limited | Sustained release pharmaceutical composition |
| US5540945A (en) * | 1989-05-11 | 1996-07-30 | Chugai Seiyaku Kabushiki Kaisha | Pharmaceutical preparations for oral administration that are adapted to release the drug at appropriate sites in the intestines |
| JP2967492B2 (ja) * | 1989-05-11 | 1999-10-25 | 中外製薬株式会社 | 腸内適所放出経口製剤 |
| FI94339C (sv) | 1989-07-21 | 1995-08-25 | Warner Lambert Co | Förfarande för framställning av farmaceutiskt användbar /R-(R*,R*)/-2-(4-fluorfenyl)- , -dihydroxi-5-(1-metyletyl)-3-fenyl-4-/(fenylamino)karbonyl/-1H-pyrrol-1-heptansyra och farmaceutiskt användbara salter därav |
| PH27186A (en) * | 1989-09-07 | 1993-04-16 | Ciba Geigy Ag | Double-coated granules of disodium pamidronate |
| US5204118A (en) * | 1989-11-02 | 1993-04-20 | Mcneil-Ppc, Inc. | Pharmaceutical compositions and methods for treating the symptoms of overindulgence |
| KR930000861B1 (ko) * | 1990-02-27 | 1993-02-08 | 한미약품공업 주식회사 | 오메프라졸 직장투여 조성물 |
| CA2052698A1 (en) * | 1990-10-11 | 1992-04-12 | Roger G. Berlin | Treatment of peptic ulcer |
| US5316772A (en) * | 1990-12-19 | 1994-05-31 | Solvay & Cie, S.A. (Societe Anonyme) | Bilayered oral pharmaceutical composition with pH dependent release |
| US5232706A (en) * | 1990-12-31 | 1993-08-03 | Esteve Quimica, S.A. | Oral pharmaceutical preparation containing omeprazol |
| YU48263B (sh) * | 1991-06-17 | 1997-09-30 | Byk Gulden Lomberg Chemische Fabrik Gmbh. | Postupak za dobijanje farmaceutskog preparata na bazi pantoprazola |
| DE69127275T2 (de) * | 1991-06-21 | 1998-03-12 | Ilsan Ilac Ve Hammaddeleri San | Neues galenisches Verfahren für Omeprazol enthaltende Pellets |
| US6764697B1 (en) * | 1991-06-27 | 2004-07-20 | Alza Corporation | System for delaying drug delivery up to seven hours |
| HU9202318D0 (en) * | 1991-07-22 | 1992-10-28 | Bristol Myers Squibb Co | Method for preparing medical preparatives containing didesoxi-purine nucleoside |
| CA2122479C (en) * | 1991-11-22 | 1998-08-25 | Richard John Dansereau | Risedronate delayed-release compositions |
| HU9203780D0 (en) * | 1991-12-12 | 1993-03-29 | Sandoz Ag | Stabilized pharmaceutical products of hmg-coa reductase inhibitor and method for producing them |
| US5681585A (en) * | 1991-12-24 | 1997-10-28 | Euro-Celtique, S.A. | Stabilized controlled release substrate having a coating derived from an aqueous dispersion of hydrophobic polymer |
| US5968551A (en) * | 1991-12-24 | 1999-10-19 | Purdue Pharma L.P. | Orally administrable opioid formulations having extended duration of effect |
| US5472712A (en) * | 1991-12-24 | 1995-12-05 | Euroceltique, S.A. | Controlled-release formulations coated with aqueous dispersions of ethylcellulose |
| US5580578A (en) * | 1992-01-27 | 1996-12-03 | Euro-Celtique, S.A. | Controlled release formulations coated with aqueous dispersions of acrylic polymers |
| US7070806B2 (en) * | 1992-01-27 | 2006-07-04 | Purdue Pharma Lp | Controlled release formulations coated with aqueous dispersions of acrylic polymers |
| FR2692146B1 (fr) * | 1992-06-16 | 1995-06-02 | Ethypharm Sa | Compositions stables de microgranules d'omeprazole gastro-protégés et leur procédé d'obtention. |
| AU4513393A (en) * | 1992-07-17 | 1994-02-14 | Astra Aktiebolag | Pharmaceutical composition containing antiulcer agent |
| GB9223702D0 (en) | 1992-11-12 | 1992-12-23 | Lucas Ind Plc | Improvements in hydraulic braking systems for vehicles |
| DE69425453T2 (de) * | 1993-04-23 | 2001-04-12 | Novartis Ag, Basel | Wirkstoffabgabevorrichtung mit gesteuerter Freigabe |
| SE9301489D0 (sv) * | 1993-04-30 | 1993-04-30 | Ab Astra | Veterinary composition |
| SE9301830D0 (sv) * | 1993-05-28 | 1993-05-28 | Ab Astra | New compounds |
| US6875872B1 (en) | 1993-05-28 | 2005-04-05 | Astrazeneca | Compounds |
| SE9302396D0 (sv) * | 1993-07-09 | 1993-07-09 | Ab Astra | A novel compound form |
| SE9302395D0 (sv) * | 1993-07-09 | 1993-07-09 | Ab Astra | New pharmaceutical formulation |
| TW397686B (en) * | 1993-08-11 | 2000-07-11 | Takeda Chemical Industries Ltd | Antacid compositions and pharmaceutical compositions |
| TW280770B (sv) | 1993-10-15 | 1996-07-11 | Takeda Pharm Industry Co Ltd | |
| US5714505A (en) * | 1994-01-05 | 1998-02-03 | Astra Aktiebolag | Method for treatment of psoriasis, by omeprazole or related compounds |
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-
1986
- 1986-04-30 GB GB08610572A patent/GB2189698A/en not_active Withdrawn
-
1987
- 1987-04-01 ZA ZA872378A patent/ZA872378B/xx unknown
- 1987-04-15 YU YU68187A patent/YU46192B/sh unknown
- 1987-04-15 SI SI8710681A patent/SI8710681A8/sl unknown
- 1987-04-16 ES ES93201611T patent/ES2135443T3/es not_active Expired - Lifetime
- 1987-04-16 AT AT92107179T patent/ATE140387T1/de not_active IP Right Cessation
- 1987-04-16 EP EP93201611A patent/EP0567201B1/en not_active Revoked
- 1987-04-16 ES ES92107179T patent/ES2091971T3/es not_active Expired - Lifetime
- 1987-04-16 EP EP92107179A patent/EP0496437B1/en not_active Expired - Lifetime
- 1987-04-16 DE DE3751860T patent/DE3751860T2/de not_active Ceased
- 1987-04-16 EP EP87850127A patent/EP0247983B1/en not_active Expired - Lifetime
- 1987-04-16 AT AT87850127T patent/ATE84215T1/de not_active IP Right Cessation
- 1987-04-16 DE DE198787850127T patent/DE247983T1/de active Pending
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- 1987-04-16 DE DE8787850127T patent/DE3783394T2/de not_active Ceased
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- 1987-04-20 US US07/040,491 patent/US4786505A/en not_active Expired - Lifetime
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- 1987-04-28 DK DK215887A patent/DK169988B1/da not_active IP Right Cessation
- 1987-04-28 IE IE110787A patent/IE61416B1/en not_active IP Right Cessation
- 1987-04-28 DZ DZ870069A patent/DZ1077A1/fr active
- 1987-04-28 IS IS3221A patent/IS1917B/is unknown
- 1987-04-29 KR KR1019870004132A patent/KR910004579B1/ko not_active Expired
- 1987-04-29 PT PT84785A patent/PT84785B/pt unknown
- 1987-04-29 PL PL1987265416A patent/PL151631B1/pl unknown
- 1987-04-29 HU HU871948A patent/HU196708B/hu active IP Right Maintenance
- 1987-04-29 CA CA000535899A patent/CA1292693C/en not_active Expired - Lifetime
- 1987-04-29 FI FI871913A patent/FI90393C/sv not_active IP Right Cessation
- 1987-04-29 RU SU874202525A patent/RU1820837C/ru active
- 1987-04-29 DD DD87302262A patent/DD273197A5/de unknown
- 1987-04-29 NO NO871790A patent/NO174239C/no unknown
- 1987-04-30 CN CN87103284A patent/CN1020852C/zh not_active Expired - Lifetime
- 1987-04-30 JP JP62108762A patent/JPS62258320A/ja active Granted
- 1987-04-30 AR AR307447A patent/AR240250A1/es active
- 1987-06-18 IL IL82911A patent/IL82911A/xx not_active IP Right Cessation
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1989
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-
1991
- 1991-12-20 JP JP3355985A patent/JP2740993B2/ja not_active Expired - Lifetime
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1992
- 1992-04-24 RU SU925011683A patent/RU2095054C1/ru active
- 1992-10-02 HR HRP-681/87A patent/HRP920854B1/xx not_active IP Right Cessation
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1993
- 1993-03-23 GR GR930400621T patent/GR3007434T3/el unknown
- 1993-06-28 LV LVP-93-694A patent/LV10357B/en unknown
- 1993-12-28 LT LTIP1683A patent/LT3699B/lt not_active IP Right Cessation
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1994
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- 1994-12-01 HK HK135294A patent/HK135294A/en not_active IP Right Cessation
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1995
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1996
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1997
- 1997-04-24 HK HK52897A patent/HK52897A/en not_active IP Right Cessation
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1999
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BB | Publication of examined application | ||
| FG | Patent granted |
Owner name: AKTIEBOLAGET HAESSLE |
|
| MA | Patent expired |