CA2258918C - Stable drug form for oral administration with benzimidazole derivatives as active ingredient and process for the preparation thereof - Google Patents
Stable drug form for oral administration with benzimidazole derivatives as active ingredient and process for the preparation thereof Download PDFInfo
- Publication number
- CA2258918C CA2258918C CA002258918A CA2258918A CA2258918C CA 2258918 C CA2258918 C CA 2258918C CA 002258918 A CA002258918 A CA 002258918A CA 2258918 A CA2258918 A CA 2258918A CA 2258918 C CA2258918 C CA 2258918C
- Authority
- CA
- Canada
- Prior art keywords
- medicament according
- gastric juice
- intermediate layer
- layer
- medicament
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000003814 drug Substances 0.000 title claims abstract description 90
- 239000004480 active ingredient Substances 0.000 title claims abstract description 51
- 238000000034 method Methods 0.000 title claims abstract description 17
- 229940079593 drug Drugs 0.000 title abstract description 7
- 238000002360 preparation method Methods 0.000 title abstract description 5
- 230000008569 process Effects 0.000 title abstract description 3
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title description 3
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 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 abstract description 94
- 229960000381 omeprazole Drugs 0.000 claims abstract description 80
- 210000004051 gastric juice Anatomy 0.000 claims abstract description 57
- 239000000463 material Substances 0.000 claims abstract description 31
- IQPSEEYGBUAQFF-UHFFFAOYSA-N Pantoprazole Chemical compound COC1=CC=NC(CS(=O)C=2NC3=CC=C(OC(F)F)C=C3N=2)=C1OC IQPSEEYGBUAQFF-UHFFFAOYSA-N 0.000 claims abstract description 12
- MJIHNNLFOKEZEW-UHFFFAOYSA-N lansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1 MJIHNNLFOKEZEW-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229960003174 lansoprazole Drugs 0.000 claims abstract description 11
- 229960005019 pantoprazole Drugs 0.000 claims abstract description 11
- 238000005341 cation exchange Methods 0.000 claims abstract description 6
- 239000010410 layer Substances 0.000 claims description 144
- 239000000543 intermediate Substances 0.000 claims description 50
- 239000008188 pellet Substances 0.000 claims description 49
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
- 239000012048 reactive intermediate Substances 0.000 claims description 22
- 229920000642 polymer Polymers 0.000 claims description 18
- 239000002671 adjuvant Substances 0.000 claims description 17
- 239000006185 dispersion Substances 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 16
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims description 15
- 229960001259 diclofenac Drugs 0.000 claims description 15
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical group OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 13
- 239000003513 alkali Substances 0.000 claims description 13
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 claims description 13
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 claims description 13
- 235000010355 mannitol Nutrition 0.000 claims description 13
- 239000002775 capsule Substances 0.000 claims description 12
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 11
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 claims description 10
- 239000008187 granular material Substances 0.000 claims description 10
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 10
- 239000000454 talc Substances 0.000 claims description 10
- 235000012222 talc Nutrition 0.000 claims description 10
- 229910052623 talc Inorganic materials 0.000 claims description 10
- 239000001069 triethyl citrate Substances 0.000 claims description 10
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 claims description 10
- 235000013769 triethyl citrate Nutrition 0.000 claims description 10
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 8
- 235000019333 sodium laurylsulphate Nutrition 0.000 claims description 8
- 229920000623 Cellulose acetate phthalate Polymers 0.000 claims description 7
- 229940081734 cellulose acetate phthalate Drugs 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 230000035515 penetration Effects 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- -1 sorbitan fatty acid ester Chemical class 0.000 claims description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- 229920003135 Eudragit® L 100-55 Polymers 0.000 claims description 5
- 208000007107 Stomach Ulcer Diseases 0.000 claims description 5
- 208000000718 duodenal ulcer Diseases 0.000 claims description 5
- 239000003974 emollient agent Substances 0.000 claims description 5
- 238000009472 formulation Methods 0.000 claims description 5
- 201000005917 gastric ulcer Diseases 0.000 claims description 5
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 5
- 208000000689 peptic esophagitis Diseases 0.000 claims description 5
- 208000011580 syndromic disease Diseases 0.000 claims description 5
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- 230000027119 gastric acid secretion Effects 0.000 claims description 4
- 230000005764 inhibitory process Effects 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 3
- 239000007963 capsule composition Substances 0.000 claims description 3
- 239000002356 single layer Substances 0.000 claims description 3
- 239000003086 colorant Substances 0.000 claims description 2
- 239000000049 pigment Substances 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 230000007704 transition Effects 0.000 claims description 2
- WEAPVABOECTMGR-UHFFFAOYSA-N triethyl 2-acetyloxypropane-1,2,3-tricarboxylate Chemical compound CCOC(=O)CC(C(=O)OCC)(OC(C)=O)CC(=O)OCC WEAPVABOECTMGR-UHFFFAOYSA-N 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 229920003139 Eudragit® L 100 Polymers 0.000 claims 2
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims 1
- 239000004698 Polyethylene Substances 0.000 claims 1
- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- 238000010030 laminating Methods 0.000 claims 1
- 229920000573 polyethylene Polymers 0.000 claims 1
- 239000004615 ingredient Substances 0.000 abstract description 2
- 239000011162 core material Substances 0.000 description 45
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 33
- 229920003134 Eudragit® polymer Polymers 0.000 description 32
- 238000003860 storage Methods 0.000 description 30
- 230000002378 acidificating effect Effects 0.000 description 16
- 238000000576 coating method Methods 0.000 description 16
- 239000000126 substance Substances 0.000 description 15
- 239000011248 coating agent Substances 0.000 description 14
- 239000007857 degradation product Substances 0.000 description 10
- 239000002609 medium Substances 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 9
- 230000015556 catabolic process Effects 0.000 description 8
- 238000006731 degradation reaction Methods 0.000 description 8
- 239000012055 enteric layer Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 230000006870 function Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000002845 discoloration Methods 0.000 description 6
- 229910000397 disodium phosphate Inorganic materials 0.000 description 6
- 210000000813 small intestine Anatomy 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 210000002784 stomach Anatomy 0.000 description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000006172 buffering agent Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 230000000968 intestinal effect Effects 0.000 description 5
- 210000000936 intestine Anatomy 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 238000001665 trituration Methods 0.000 description 5
- 208000025865 Ulcer Diseases 0.000 description 4
- 230000004888 barrier function Effects 0.000 description 4
- 239000011247 coating layer Substances 0.000 description 4
- 238000010276 construction Methods 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 4
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 206010061218 Inflammation Diseases 0.000 description 3
- 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 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 150000001556 benzimidazoles Chemical class 0.000 description 3
- 230000003139 buffering effect Effects 0.000 description 3
- 239000013065 commercial product Substances 0.000 description 3
- 150000004679 hydroxides Chemical class 0.000 description 3
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 3
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 239000002861 polymer material Substances 0.000 description 3
- 230000004224 protection Effects 0.000 description 3
- 239000011241 protective layer Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000013112 stability test Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 231100000397 ulcer Toxicity 0.000 description 3
- 239000001828 Gelatine Substances 0.000 description 2
- 238000012404 In vitro experiment Methods 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 description 2
- 230000003113 alkalizing effect Effects 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 238000002144 chemical decomposition reaction Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012792 core layer Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 210000001198 duodenum Anatomy 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 159000000011 group IA salts Chemical class 0.000 description 2
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 2
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 2
- OJLOPKGSLYJEMD-URPKTTJQSA-N methyl 7-[(1r,2r,3r)-3-hydroxy-2-[(1e)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoate Chemical compound CCCCC(C)(O)C\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC OJLOPKGSLYJEMD-URPKTTJQSA-N 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 229960005249 misoprostol Drugs 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 230000000149 penetrating effect Effects 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 238000005464 sample preparation method Methods 0.000 description 2
- 230000035882 stress Effects 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- OJLOPKGSLYJEMD-LNQMSSPSSA-N Cyotec Chemical compound CCCCC(C)(O)CC=C[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC OJLOPKGSLYJEMD-LNQMSSPSSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 206010061459 Gastrointestinal ulcer Diseases 0.000 description 1
- 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 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940097776 arthrotec Drugs 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 229940099371 diacetylated monoglycerides Drugs 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940076247 disodium hydrogen phosphate dehydrate Drugs 0.000 description 1
- 239000002702 enteric coating Substances 0.000 description 1
- 238000009505 enteric coating Methods 0.000 description 1
- GDCRSXZBSIRSFR-UHFFFAOYSA-N ethyl prop-2-enoate;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CCOC(=O)C=C GDCRSXZBSIRSFR-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000010579 first pass effect Methods 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 210000004211 gastric acid Anatomy 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 238000010874 in vitro model Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000009993 protective function Effects 0.000 description 1
- 230000009979 protective mechanism Effects 0.000 description 1
- 210000001187 pylorus Anatomy 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 239000004554 water soluble tablet Substances 0.000 description 1
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
- A61K9/48—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
- 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
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
-
- 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
- A61K9/5084—Mixtures of one or more drugs in different galenical forms, at least one of which being granules, microcapsules or (coated) microparticles according to A61K9/16 or A61K9/50, e.g. for obtaining a specific release pattern or for combining different drugs
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19626045.0 | 1996-06-28 | ||
| DE19626045A DE19626045C2 (de) | 1996-06-28 | 1996-06-28 | Stabile Arzneiform zur oralen Verabreichung, welche Omeprazol als aktiven Wirkstoff enthält, sowie Verfahren zur Herstellung derselben |
| PCT/EP1997/003387 WO1998000114A2 (de) | 1996-06-28 | 1997-06-27 | Stabile arzneiform mit benzimidazolderivaten als wirkstoff zur oralen verabreichung und verfahren zu ihrer herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2258918A1 CA2258918A1 (en) | 1998-01-08 |
| CA2258918C true CA2258918C (en) | 2005-11-22 |
Family
ID=7798347
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002258918A Expired - Fee Related CA2258918C (en) | 1996-06-28 | 1997-06-27 | Stable drug form for oral administration with benzimidazole derivatives as active ingredient and process for the preparation thereof |
Country Status (11)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10537530B2 (en) | 2007-05-07 | 2020-01-21 | Evonik Operations Gmbh | Solid dosage forms comprising an enteric coating with accelerated drug release |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5840737A (en) | 1996-01-04 | 1998-11-24 | The Curators Of The University Of Missouri | Omeprazole solution and method for using same |
| US6489346B1 (en) | 1996-01-04 | 2002-12-03 | The Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and method of using same |
| SE9704869D0 (sv) * | 1997-12-22 | 1997-12-22 | Astra Ab | New pharmaceutical formulaton II |
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| SE9302395D0 (sv) * | 1993-07-09 | 1993-07-09 | Ab Astra | New pharmaceutical formulation |
-
1996
- 1996-06-28 DE DE19626045A patent/DE19626045C2/de not_active Expired - Fee Related
-
1997
- 1997-06-27 PT PT97929304T patent/PT934058E/pt unknown
- 1997-06-27 AU AU33451/97A patent/AU3345197A/en not_active Abandoned
- 1997-06-27 ES ES97929304T patent/ES2205243T3/es not_active Expired - Lifetime
- 1997-06-27 CA CA002258918A patent/CA2258918C/en not_active Expired - Fee Related
- 1997-06-27 AU AU34388/97A patent/AU3438897A/en not_active Abandoned
- 1997-06-27 JP JP50383698A patent/JP4641075B2/ja not_active Expired - Fee Related
- 1997-06-27 WO PCT/EP1997/003387 patent/WO1998000114A2/de active IP Right Grant
- 1997-06-27 WO PCT/EP1997/003388 patent/WO1998000115A2/de active Application Filing
- 1997-06-27 AT AT97929304T patent/ATE247457T1/de active
- 1997-06-27 DK DK97929304T patent/DK0934058T3/da active
- 1997-06-27 EP EP97929304A patent/EP0934058B1/de not_active Expired - Lifetime
- 1997-06-27 DE DE59710629T patent/DE59710629D1/de not_active Expired - Lifetime
- 1997-06-30 ZA ZA9705827A patent/ZA975827B/xx unknown
- 1997-06-30 ZA ZA9705828A patent/ZA975828B/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10537530B2 (en) | 2007-05-07 | 2020-01-21 | Evonik Operations Gmbh | Solid dosage forms comprising an enteric coating with accelerated drug release |
Also Published As
| Publication number | Publication date |
|---|---|
| PT934058E (pt) | 2004-01-30 |
| EP0934058B1 (de) | 2003-08-20 |
| WO1998000114A3 (de) | 1998-02-26 |
| DE59710629D1 (de) | 2003-09-25 |
| WO1998000115A3 (de) | 1998-02-26 |
| JP4641075B2 (ja) | 2011-03-02 |
| ATE247457T1 (de) | 2003-09-15 |
| WO1998000114A2 (de) | 1998-01-08 |
| CA2258918A1 (en) | 1998-01-08 |
| DE19626045C2 (de) | 1998-12-03 |
| AU3438897A (en) | 1998-01-21 |
| DK0934058T3 (da) | 2003-12-01 |
| WO1998000115A2 (de) | 1998-01-08 |
| ES2205243T3 (es) | 2004-05-01 |
| JP2000514051A (ja) | 2000-10-24 |
| DE19626045A1 (de) | 1998-01-08 |
| ZA975828B (en) | 1998-01-30 |
| AU3345197A (en) | 1998-01-21 |
| EP0934058A2 (de) | 1999-08-11 |
| ZA975827B (en) | 1998-01-30 |
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