CA2563162C - Forme posologique contenant du pantoprazole en tant qu'ingredient actif - Google Patents
Forme posologique contenant du pantoprazole en tant qu'ingredient actif Download PDFInfo
- Publication number
- CA2563162C CA2563162C CA2563162A CA2563162A CA2563162C CA 2563162 C CA2563162 C CA 2563162C CA 2563162 A CA2563162 A CA 2563162A CA 2563162 A CA2563162 A CA 2563162A CA 2563162 C CA2563162 C CA 2563162C
- Authority
- CA
- Canada
- Prior art keywords
- dosage form
- molecular weight
- pantoprazole
- tablet
- form according
- 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 - Lifetime
Links
- 239000002552 dosage form Substances 0.000 title claims abstract description 89
- 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 title claims abstract description 74
- 229960005019 pantoprazole Drugs 0.000 title claims abstract description 70
- 239000004480 active ingredient Substances 0.000 title description 18
- 239000008188 pellet Substances 0.000 claims description 125
- 239000003826 tablet Substances 0.000 claims description 113
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 112
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 109
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 105
- 239000010410 layer Substances 0.000 claims description 82
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 66
- 239000002702 enteric coating Substances 0.000 claims description 41
- 238000009505 enteric coating Methods 0.000 claims description 41
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 35
- RDRUTBCDIVCMMX-UHFFFAOYSA-N magnesium;5-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]benzimidazol-1-ide Chemical compound [Mg+2].COC1=CC=NC(CS(=O)C=2[N-]C3=CC=C(OC(F)F)C=C3N=2)=C1OC.COC1=CC=NC(CS(=O)C=2[N-]C3=CC=C(OC(F)F)C=C3N=2)=C1OC RDRUTBCDIVCMMX-UHFFFAOYSA-N 0.000 claims description 34
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 33
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 32
- 239000000725 suspension Substances 0.000 claims description 30
- 238000009498 subcoating Methods 0.000 claims description 27
- 239000011230 binding agent Substances 0.000 claims description 22
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 22
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 21
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 20
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 20
- 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 19
- 210000004051 gastric juice Anatomy 0.000 claims description 19
- -1 pantoprazole magne-sium dihydrate Chemical class 0.000 claims description 19
- 229930195725 Mannitol Natural products 0.000 claims description 18
- 239000000594 mannitol Substances 0.000 claims description 18
- 235000010355 mannitol Nutrition 0.000 claims description 18
- 239000007864 aqueous solution Substances 0.000 claims description 17
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 16
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 16
- 235000019333 sodium laurylsulphate Nutrition 0.000 claims description 16
- 238000002156 mixing Methods 0.000 claims description 15
- 239000002775 capsule Substances 0.000 claims description 14
- 238000001035 drying Methods 0.000 claims description 14
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 14
- 229940083575 sodium dodecyl sulfate Drugs 0.000 claims description 14
- 229960000913 crospovidone Drugs 0.000 claims description 13
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 13
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 claims description 13
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 claims description 13
- 229920000881 Modified starch Polymers 0.000 claims description 12
- 229920002472 Starch Polymers 0.000 claims description 12
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 claims description 12
- 235000013539 calcium stearate Nutrition 0.000 claims description 12
- 239000008116 calcium stearate Substances 0.000 claims description 12
- 229940078456 calcium stearate Drugs 0.000 claims description 12
- 208000000718 duodenal ulcer Diseases 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- 241000590002 Helicobacter pylori Species 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 11
- 229940037467 helicobacter pylori Drugs 0.000 claims description 11
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 11
- 229940001593 sodium carbonate Drugs 0.000 claims description 11
- 235000019698 starch Nutrition 0.000 claims description 11
- 239000008107 starch Substances 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
- 239000012055 enteric layer Substances 0.000 claims description 10
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 10
- 239000004408 titanium dioxide Substances 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
- 230000002496 gastric effect Effects 0.000 claims description 9
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 9
- 239000007858 starting material Substances 0.000 claims description 9
- 208000007107 Stomach Ulcer Diseases 0.000 claims description 8
- 201000005917 gastric ulcer Diseases 0.000 claims description 8
- 238000011321 prophylaxis Methods 0.000 claims description 8
- 235000019359 magnesium stearate Nutrition 0.000 claims description 7
- 210000000813 small intestine Anatomy 0.000 claims description 7
- 229930006000 Sucrose Natural products 0.000 claims description 6
- 239000000945 filler Substances 0.000 claims description 6
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 6
- 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 6
- 229940126409 proton pump inhibitor Drugs 0.000 claims description 6
- 239000000612 proton pump inhibitor Substances 0.000 claims description 6
- 239000005720 sucrose Substances 0.000 claims 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 claims description 5
- 239000003242 anti bacterial agent Substances 0.000 claims description 5
- 229940088710 antibiotic agent Drugs 0.000 claims description 5
- 230000003111 delayed effect Effects 0.000 claims description 5
- 238000005507 spraying Methods 0.000 claims description 5
- 201000008629 Zollinger-Ellison syndrome Diseases 0.000 claims description 4
- 238000002648 combination therapy Methods 0.000 claims description 4
- 230000008029 eradication Effects 0.000 claims description 4
- 201000000052 gastrinoma Diseases 0.000 claims description 4
- 229960001855 mannitol Drugs 0.000 claims description 4
- 230000007935 neutral effect Effects 0.000 claims description 4
- 229920006316 polyvinylpyrrolidine Polymers 0.000 claims description 4
- 239000000080 wetting agent Substances 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 238000011049 filling Methods 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 235000017550 sodium carbonate Nutrition 0.000 claims 7
- 150000002484 inorganic compounds Chemical class 0.000 claims 4
- 229910010272 inorganic material Inorganic materials 0.000 claims 4
- 229920003134 Eudragit® polymer Polymers 0.000 claims 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 229940057948 magnesium stearate Drugs 0.000 claims 1
- 239000007909 solid dosage form Substances 0.000 claims 1
- 159000000003 magnesium salts Chemical class 0.000 abstract description 48
- 239000011162 core material Substances 0.000 description 74
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
- 229940053326 magnesium salt Drugs 0.000 description 46
- 238000000576 coating method Methods 0.000 description 45
- 239000011248 coating agent Substances 0.000 description 42
- 238000000034 method Methods 0.000 description 35
- 239000000203 mixture Substances 0.000 description 30
- 150000001875 compounds Chemical class 0.000 description 27
- 230000008569 process Effects 0.000 description 24
- 239000006186 oral dosage form Substances 0.000 description 23
- 150000004683 dihydrates Chemical class 0.000 description 22
- 239000008187 granular material Substances 0.000 description 21
- 239000011777 magnesium Substances 0.000 description 19
- 238000001125 extrusion Methods 0.000 description 16
- 239000006185 dispersion Substances 0.000 description 14
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 13
- 239000008108 microcrystalline cellulose Substances 0.000 description 13
- 229940016286 microcrystalline cellulose Drugs 0.000 description 13
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 13
- 239000008213 purified water Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 239000000126 substance Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 238000005563 spheronization Methods 0.000 description 9
- WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 description 8
- 239000001828 Gelatine Substances 0.000 description 8
- 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 8
- 229920000159 gelatin Polymers 0.000 description 8
- 235000019322 gelatine Nutrition 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 8
- 229960001021 lactose monohydrate Drugs 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 239000000314 lubricant Substances 0.000 description 7
- 229940032147 starch Drugs 0.000 description 7
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- 239000000454 talc Substances 0.000 description 5
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- 229910052623 talc Inorganic materials 0.000 description 5
- PWWDEIMGEBPTJL-UHFFFAOYSA-N 1-(pyridin-2-ylmethylsulfinyl)benzimidazole Chemical class C1=NC2=CC=CC=C2N1S(=O)CC1=CC=CC=N1 PWWDEIMGEBPTJL-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
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- 229910052708 sodium Inorganic materials 0.000 description 4
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- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 4
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- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 229960003022 amoxicillin Drugs 0.000 description 3
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229960002626 clarithromycin Drugs 0.000 description 3
- AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@](C)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 description 3
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229960000282 metronidazole Drugs 0.000 description 3
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 3
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- 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 description 2
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- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
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- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
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- NBFNMSULHIODTC-CYJZLJNKSA-N cefadroxil monohydrate Chemical compound O.C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=C(O)C=C1 NBFNMSULHIODTC-CYJZLJNKSA-N 0.000 description 2
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- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 2
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- 239000000796 flavoring agent Substances 0.000 description 2
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- 235000003599 food sweetener Nutrition 0.000 description 2
- 235000013773 glyceryl triacetate Nutrition 0.000 description 2
- 230000035876 healing Effects 0.000 description 2
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- 239000004407 iron oxides and hydroxides Substances 0.000 description 2
- 229960001375 lactose Drugs 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- QWDJLDTYWNBUKE-UHFFFAOYSA-L magnesium bicarbonate Chemical compound [Mg+2].OC([O-])=O.OC([O-])=O QWDJLDTYWNBUKE-UHFFFAOYSA-L 0.000 description 2
- DHRRIBDTHFBPNG-UHFFFAOYSA-L magnesium dichloride hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[Cl-].[Cl-] DHRRIBDTHFBPNG-UHFFFAOYSA-L 0.000 description 2
- CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- YNWDKZIIWCEDEE-UHFFFAOYSA-N pantoprazole sodium Chemical compound [Na+].COC1=CC=NC(CS(=O)C=2[N-]C3=CC=C(OC(F)F)C=C3N=2)=C1OC YNWDKZIIWCEDEE-UHFFFAOYSA-N 0.000 description 2
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- 239000000049 pigment Substances 0.000 description 2
- 229940069328 povidone Drugs 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
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Landscapes
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Des formes posologiques destinées à l'administration orale du sel de magnésium de pantoprazole sont divulguées.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP03010328.7 | 2003-05-08 | ||
EP03010328 | 2003-05-08 | ||
EP04001754.3 | 2004-01-28 | ||
EP04001754 | 2004-01-28 | ||
CA002489140A CA2489140C (fr) | 2003-05-08 | 2004-05-07 | Forme posologique contenant du pantoprazole en tant qu'ingredient actif |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002489140A Division CA2489140C (fr) | 2003-05-08 | 2004-05-07 | Forme posologique contenant du pantoprazole en tant qu'ingredient actif |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2563162A1 CA2563162A1 (fr) | 2004-11-18 |
CA2563162C true CA2563162C (fr) | 2012-07-10 |
Family
ID=37480467
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA2563162A Expired - Lifetime CA2563162C (fr) | 2003-05-08 | 2004-05-07 | Forme posologique contenant du pantoprazole en tant qu'ingredient actif |
Country Status (1)
Country | Link |
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CA (1) | CA2563162C (fr) |
-
2004
- 2004-05-07 CA CA2563162A patent/CA2563162C/fr not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
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CA2563162A1 (fr) | 2004-11-18 |
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Legal Events
Date | Code | Title | Description |
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EEER | Examination request |