CA2500663C - Enteric composition for the manufacture of soft capsule wall - Google Patents
Enteric composition for the manufacture of soft capsule wall Download PDFInfo
- Publication number
- CA2500663C CA2500663C CA2500663A CA2500663A CA2500663C CA 2500663 C CA2500663 C CA 2500663C CA 2500663 A CA2500663 A CA 2500663A CA 2500663 A CA2500663 A CA 2500663A CA 2500663 C CA2500663 C CA 2500663C
- Authority
- CA
- Canada
- Prior art keywords
- soft capsule
- capsule shell
- enteric
- enteric soft
- film
- 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
- 239000007901 soft capsule Substances 0.000 title claims abstract description 62
- 239000000203 mixture Substances 0.000 title claims description 36
- 238000004519 manufacturing process Methods 0.000 title abstract description 18
- 239000000499 gel Substances 0.000 claims description 75
- 229920000642 polymer Polymers 0.000 claims description 71
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 51
- 108010010803 Gelatin Proteins 0.000 claims description 25
- 229920000159 gelatin Polymers 0.000 claims description 25
- 239000008273 gelatin Substances 0.000 claims description 25
- 235000019322 gelatine Nutrition 0.000 claims description 25
- 235000011852 gelatine desserts Nutrition 0.000 claims description 25
- 239000003513 alkali Substances 0.000 claims description 22
- 239000004014 plasticizer Substances 0.000 claims description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 claims description 17
- 239000001069 triethyl citrate Substances 0.000 claims description 17
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 claims description 17
- 235000013769 triethyl citrate Nutrition 0.000 claims description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 12
- 229920003169 water-soluble polymer Polymers 0.000 claims description 12
- 239000002202 Polyethylene glycol Substances 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 10
- 229920001223 polyethylene glycol Polymers 0.000 claims description 10
- 210000000988 bone and bone Anatomy 0.000 claims description 9
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 7
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- 239000003125 aqueous solvent Substances 0.000 claims description 5
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 5
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 5
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 5
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 4
- 229920003145 methacrylic acid copolymer Polymers 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 229960004418 trolamine Drugs 0.000 claims description 4
- 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 claims description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims 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 claims description 3
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 claims description 3
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 claims description 3
- 239000000600 sorbitol Substances 0.000 claims description 3
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 claims description 2
- 229920002126 Acrylic acid copolymer Polymers 0.000 claims description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 2
- 150000001720 carbohydrates Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229920002301 cellulose acetate Polymers 0.000 claims description 2
- 150000005846 sugar alcohols Polymers 0.000 claims description 2
- 125000000837 carbohydrate group Chemical group 0.000 claims 1
- 238000000576 coating method Methods 0.000 abstract description 18
- 239000011248 coating agent Substances 0.000 abstract description 14
- 239000007902 hard capsule Substances 0.000 abstract description 8
- 239000002775 capsule Substances 0.000 description 43
- 239000003921 oil Substances 0.000 description 35
- 235000019198 oils Nutrition 0.000 description 35
- 238000004090 dissolution Methods 0.000 description 25
- 238000005538 encapsulation Methods 0.000 description 24
- 238000004458 analytical method Methods 0.000 description 22
- 238000000034 method Methods 0.000 description 20
- 230000008569 process Effects 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000002552 dosage form Substances 0.000 description 12
- 229920000623 Cellulose acetate phthalate Polymers 0.000 description 10
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 10
- 239000003826 tablet Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000010408 film Substances 0.000 description 9
- KHOITXIGCFIULA-UHFFFAOYSA-N Alophen Chemical compound C1=CC(OC(=O)C)=CC=C1C(C=1N=CC=CC=1)C1=CC=C(OC(C)=O)C=C1 KHOITXIGCFIULA-UHFFFAOYSA-N 0.000 description 8
- 235000011114 ammonium hydroxide Nutrition 0.000 description 8
- 229960000503 bisacodyl Drugs 0.000 description 8
- 239000003549 soybean oil Substances 0.000 description 8
- 235000012424 soybean oil Nutrition 0.000 description 8
- OGSPWJRAVKPPFI-UHFFFAOYSA-N Alendronic Acid Chemical compound NCCCC(O)(P(O)(O)=O)P(O)(O)=O OGSPWJRAVKPPFI-UHFFFAOYSA-N 0.000 description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 7
- 235000011941 Tilia x europaea Nutrition 0.000 description 7
- 239000000908 ammonium hydroxide Substances 0.000 description 7
- 239000004571 lime Substances 0.000 description 7
- 239000003981 vehicle Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 229960004343 alendronic acid Drugs 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 229920003139 Eudragit® L 100 Polymers 0.000 description 5
- 229920003134 Eudragit® polymer Polymers 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 238000009505 enteric coating Methods 0.000 description 5
- 239000002702 enteric coating Substances 0.000 description 5
- 229940012017 ethylenediamine Drugs 0.000 description 5
- 239000008173 hydrogenated soybean oil Substances 0.000 description 5
- 238000004904 shortening Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 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 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- 229920001800 Shellac Polymers 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 4
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 4
- 229960000907 methylthioninium chloride Drugs 0.000 description 4
- 229960000381 omeprazole Drugs 0.000 description 4
- 239000004208 shellac Substances 0.000 description 4
- 235000013874 shellac Nutrition 0.000 description 4
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 4
- 229940113147 shellac Drugs 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 235000013311 vegetables Nutrition 0.000 description 4
- 240000002234 Allium sativum Species 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 235000004611 garlic Nutrition 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 235000011118 potassium hydroxide Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000006000 Garlic extract Substances 0.000 description 2
- 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 2
- 229920002690 Polyoxyl 40 HydrogenatedCastorOil Polymers 0.000 description 2
- AOBORMOPSGHCAX-UHFFFAOYSA-N Tocophersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-UHFFFAOYSA-N 0.000 description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 235000013871 bee wax Nutrition 0.000 description 2
- 239000012166 beeswax Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 235000020706 garlic extract Nutrition 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000006186 oral dosage form Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 235000010413 sodium alginate Nutrition 0.000 description 2
- 239000000661 sodium alginate Substances 0.000 description 2
- 238000009498 subcoating Methods 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- MUZDXNQOSGWMJJ-UHFFFAOYSA-N 2-methylprop-2-enoic acid;prop-2-enoic acid Chemical compound OC(=O)C=C.CC(=C)C(O)=O MUZDXNQOSGWMJJ-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 229940062527 alendronate Drugs 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000009507 drug disintegration testing Methods 0.000 description 1
- 238000009506 drug dissolution testing Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000008184 oral solid dosage form Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 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
- 229920006254 polymer film Polymers 0.000 description 1
- 231100000683 possible toxicity Toxicity 0.000 description 1
- 235000010408 potassium alginate Nutrition 0.000 description 1
- 239000000737 potassium alginate Substances 0.000 description 1
- MZYRDLHIWXQJCQ-YZOKENDUSA-L potassium alginate Chemical compound [K+].[K+].O1[C@@H](C([O-])=O)[C@@H](OC)[C@H](O)[C@H](O)[C@@H]1O[C@@H]1[C@@H](C([O-])=O)O[C@@H](O)[C@@H](O)[C@H]1O MZYRDLHIWXQJCQ-YZOKENDUSA-L 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- -1 tri-ethyl citrate Chemical compound 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 239000011240 wet gel 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
- A61K9/4816—Wall or shell material
- A61K9/4825—Proteins, e.g. gelatin
-
- 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
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
- A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
- A61K31/355—Tocopherols, e.g. vitamin E
-
- 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
- A61K31/4402—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 2, e.g. pheniramine, bisacodyl
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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
- A61K31/435—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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/60—Salicylic acid; Derivatives thereof
- A61K31/612—Salicylic acid; Derivatives thereof having the hydroxy group in position 2 esterified, e.g. salicylsulfuric acid
- A61K31/616—Salicylic acid; Derivatives thereof having the hydroxy group in position 2 esterified, e.g. salicylsulfuric acid by carboxylic acids, e.g. acetylsalicylic acid
-
- 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
- A61K31/66—Phosphorus compounds
- A61K31/662—Phosphorus acids or esters thereof having P—C bonds, e.g. foscarnet, trichlorfon
- A61K31/663—Compounds having two or more phosphorus acid groups or esters thereof, e.g. clodronic acid, pamidronic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/88—Liliopsida (monocotyledons)
- A61K36/896—Liliaceae (Lily family), e.g. daylily, plantain lily, Hyacinth or narcissus
- A61K36/8962—Allium, e.g. garden onion, leek, garlic or chives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
-
- 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
- A61K9/4816—Wall or shell material
-
- 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
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- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/10—Laxatives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- 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
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4866—Organic macromolecular compounds
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Alternative & Traditional Medicine (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Inorganic Chemistry (AREA)
- Medical Informatics (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41518702P | 2002-10-01 | 2002-10-01 | |
| US60/415,187 | 2002-10-01 | ||
| PCT/US2003/020579 WO2004030658A1 (en) | 2002-10-01 | 2003-06-27 | Enteric composition for the manufacture of soft capsule wall |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2500663A1 CA2500663A1 (en) | 2004-04-15 |
| CA2500663C true CA2500663C (en) | 2013-05-28 |
Family
ID=32069824
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| CA2500663A Expired - Lifetime CA2500663C (en) | 2002-10-01 | 2003-06-27 | Enteric composition for the manufacture of soft capsule wall |
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| Country | Link |
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| US (2) | US8685445B2 (enExample) |
| EP (2) | EP1545475B1 (enExample) |
| JP (1) | JP5248739B2 (enExample) |
| CN (1) | CN1688294A (enExample) |
| AU (1) | AU2003299191A1 (enExample) |
| CA (1) | CA2500663C (enExample) |
| CY (1) | CY1118258T1 (enExample) |
| DK (2) | DK1545475T3 (enExample) |
| ES (2) | ES2609059T3 (enExample) |
| HU (1) | HUE031650T2 (enExample) |
| MX (1) | MXPA05003524A (enExample) |
| PT (2) | PT2772250T (enExample) |
| SI (2) | SI2772250T1 (enExample) |
| WO (1) | WO2004030658A1 (enExample) |
Families Citing this family (56)
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| US20070082046A1 (en) * | 2005-10-11 | 2007-04-12 | Banner Pharmacaps, Inc. | Enteric valproic acid |
| JP5406529B2 (ja) | 2005-10-26 | 2014-02-05 | バナー ファーマキャプス， インコーポレイテッド | カプセル充墳物としての親油性ベヒクルに基づく二重制御された放出マトリクスシステム |
| CN101360485B (zh) | 2005-10-26 | 2013-04-17 | 班纳制药公司 | 作为胶囊填充物的基于亲水性载体的双重控释基质系统 |
| US20070148248A1 (en) * | 2005-12-22 | 2007-06-28 | Banner Pharmacaps, Inc. | Gastric reflux resistant dosage forms |
| JP5183104B2 (ja) * | 2006-06-19 | 2013-04-17 | 森下仁丹株式会社 | 口臭除去用多重ソフトカプセル |
| GB0706178D0 (en) * | 2007-03-29 | 2007-05-09 | Univ Aston | Enteric pharmaceutical capsules |
| US20090253808A1 (en) | 2007-11-12 | 2009-10-08 | Pharmaceutics International, Inc. | Tri-molecular complexes and their use in drug delivery systems |
| EP2223685A4 (en) * | 2007-11-13 | 2013-08-21 | Shanghai Huiyuan Vegetal Capsule Co Ltd | HARD-GEL CELLULAR, GASTRORESISTANT AND GELATIN-FREE ENVELOPE AND PROCESS FOR PREPARING THE SAME |
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| WO2010117873A2 (en) | 2009-04-06 | 2010-10-14 | Banner Pharmacaps, Inc. | Progesterone solutions for increased bioavailability |
| WO2011100643A1 (en) * | 2010-02-12 | 2011-08-18 | Sensient Colors Inc. | Enteric coating compositions and methods of making and using the same |
| KR101900966B1 (ko) | 2010-10-26 | 2018-09-20 | 캡슈겔 벨지엄 엔브이 | 벌크한 장용성 캡슐 쉘 |
| EP2844296B1 (en) | 2012-05-02 | 2019-03-13 | Capsugel Belgium NV | Aqueous dispersions of hydroxypropyl methylcellulose acetate succinate (hpmcas) |
| CA2905367A1 (en) * | 2013-03-15 | 2014-09-25 | Banner Life Sciences Llc | Non-gelatin enteric soft capsules |
| HUE042996T2 (hu) * | 2013-04-23 | 2019-07-29 | Zx Pharma Llc | Bélben oldódó bevonatú, fehérjetartalmú alapbevonattal ellátott, több részecskét tartalmazó készítmény |
| US9504656B2 (en) | 2013-10-21 | 2016-11-29 | Banner Life Sciences, LLC | Pharmaceutical compositions for poorly soluble active ingredients |
| MX2016004487A (es) | 2013-10-30 | 2016-11-10 | Banner Life Sciences Llc | Capsulas blandas de capa entérica que constan de ácidos grasos poli insaturados. |
| EP3065720A1 (en) | 2013-11-04 | 2016-09-14 | Capsugel Belgium NV | Methods and systems for improved bioavailability of active pharmaceutical ingredients including esomeprazole |
| US9636318B2 (en) | 2015-08-31 | 2017-05-02 | Banner Life Sciences Llc | Fumarate ester dosage forms |
| US9326947B1 (en) | 2014-02-28 | 2016-05-03 | Banner Life Sciences Llc | Controlled release fumarate esters |
| EP3501510B1 (en) | 2014-02-28 | 2020-07-01 | Banner Life Sciences LLC | Controlled release enteric soft capsules of fumarate esters |
| US10098863B2 (en) | 2014-02-28 | 2018-10-16 | Banner Life Sciences Llc | Fumarate esters |
| US10182992B2 (en) | 2014-04-07 | 2019-01-22 | Patheon Softgels Inc. | Abuse-deterrent controlled release formulations |
| US10772842B2 (en) | 2015-01-09 | 2020-09-15 | Patheon Softgels Inc. | Abuse-deterrent opioids |
| CA2950203C (en) | 2014-06-20 | 2019-09-03 | Banner Life Sciences Llc | Enteric soft capsule compositions |
| US20150366814A1 (en) | 2014-06-23 | 2015-12-24 | Banner Life Sciences Llc | All-natural enteric soft capsules comprising active ingredients |
| WO2015200563A1 (en) * | 2014-06-26 | 2015-12-30 | Banner Life Sciences Llc | Enhanced bioavailability of polysaturated fatty acids |
| US9895333B2 (en) | 2014-06-26 | 2018-02-20 | Patheon Softgels Inc. | Enhanced bioavailability of polyunsaturated fatty acids |
| US10471152B2 (en) | 2014-08-29 | 2019-11-12 | Capsugel Belgium Nv | Colloidal dispersion comprising HPMCAS |
| SG11201702752RA (en) | 2014-10-06 | 2017-06-29 | Fuji Capsule Co Ltd | Method of Manufacturing Enteric Seamless Soft Capsule |
| WO2016056230A1 (ja) | 2014-10-06 | 2016-04-14 | 富士カプセル株式会社 | 腸溶性ソフトカプセルの製造方法 |
| AU2015328676B2 (en) * | 2014-10-08 | 2017-07-20 | Banner Life Sciences Llc | Controlled release enteric soft capsules of fumarate esters |
| WO2016161125A1 (en) * | 2015-03-31 | 2016-10-06 | University Of Vermont And State Agricultural College | Methods for treating cryptosporidiosis using triazolopyridazines |
| US10182993B2 (en) | 2015-04-06 | 2019-01-22 | Patheon Softgels Inc. | Compositions for colonic delivery of drugs |
| KR102851614B1 (ko) | 2016-02-04 | 2025-08-29 | 신돔 파마, 인크. | 장애 치료를 위한 중수소화된 돔페리돈 조성물 및 방법 |
| PL239878B1 (pl) | 2016-03-30 | 2022-01-24 | Gdanski Univ Medyczny | Wodna kompozycja oraz sposób wytwarzania dojelitowych elastycznych filmów do sporządzania kapsułek z wodnej kompozycji oraz dojelitowy elastyczny film do sporządzania kapsułek miękkich |
| NL2017219B1 (en) * | 2016-07-22 | 2018-01-30 | Rousselot B V | Low cross-linking gelatine |
| ES2958616T3 (es) | 2017-03-08 | 2024-02-12 | Cinrx Pharma Llc | Formulaciones farmacéuticas de floroglucinol y trimetilfloroglucinol |
| KR20240125702A (ko) | 2017-06-30 | 2024-08-19 | 신돔 파마, 인크. | 중수소화 돔페리돈 조성물, 방법, 및 제조 |
| US12478612B2 (en) | 2017-06-30 | 2025-11-25 | Cindome Pharma, Inc. | Deuterated domperidone compositions, methods, and preparation |
| WO2019178444A1 (en) | 2018-03-15 | 2019-09-19 | R.P. Scherer Technologies, Llc | Enteric softgel capsules |
| CN108619523B (zh) * | 2018-03-23 | 2020-06-30 | 浙江工业大学 | 一种可用于快速热塑包衣制剂的包衣膜片及其制备方法 |
| WO2020144591A2 (en) * | 2019-01-09 | 2020-07-16 | Antony Benny | Preparation of purified withanoside x from withania somnifera plant materials and its medicinal use for the treatment of health disorders |
| CN109566829A (zh) * | 2019-02-11 | 2019-04-05 | 广东国方医药科技有限公司 | 牡丹籽油肠溶凝胶糖果及其制备方法 |
| US11547714B2 (en) | 2020-02-05 | 2023-01-10 | Epalex Corporation | Fospropofol salts, methods and compositions |
| US11478490B1 (en) | 2021-03-30 | 2022-10-25 | Epalex Corporation | Fospropofol formulations |
| US11439653B1 (en) | 2021-03-30 | 2022-09-13 | Epalex Corporation | Fospropofol formulations |
| US11628178B2 (en) | 2019-03-26 | 2023-04-18 | Epalex Corporation | Fospropofol methods and compositions |
| MX2021013488A (es) | 2019-05-07 | 2021-12-10 | Bausch Health Ireland Ltd | Formulaciones liquidas de dosis oral de metilnaltrexona. |
| WO2021011177A1 (en) * | 2019-07-15 | 2021-01-21 | R.P. Scherer Technologies, Llc | Enteric proton pump inhibitor softgel capsule |
| WO2021142062A1 (en) | 2020-01-10 | 2021-07-15 | Banner Life Sciences Llc | Fumarate ester dosage forms with enhanced gastrointestinal tolerability |
| EP4142727A1 (en) | 2020-05-02 | 2023-03-08 | Bausch Health Ireland Limited | Methods of reducing mortality risk in subjects suffering from an underlying disease or condition by administration of methylnaltrexone |
| CA3119012C (en) * | 2021-05-18 | 2023-10-17 | Gelentroceutics Inc. | Formulation of intrinsically acid-resistant vegetarian-based and gelatin-based soft gel capsules for pharmaceutical/nutraceutical products |
| KR20250026264A (ko) | 2022-06-21 | 2025-02-25 | 뉴트리션 ＆ 바이오사이언시즈 유에스에이 1, 엘엘씨 | 경질 셸 캡슐, 막 및 코팅을 위한 막 형성 지연형/장용 제형 |
| WO2024254058A1 (en) * | 2023-06-06 | 2024-12-12 | R.P. Scherer Technologies, Llc | Ambroxol liquid formulation |
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| US3826666A (en) * | 1972-07-20 | 1974-07-30 | Parke Davis & Co | Enteric capsules |
| DE2340060A1 (de) * | 1973-08-08 | 1975-02-20 | Scherer Gmbh R P | Magensaftresistente gelatinekapseln und verfahren zu deren herstellung |
| US4138013A (en) * | 1976-08-27 | 1979-02-06 | Parke, Davis & Company | Enteric capsules |
| GR78492B (enExample) * | 1982-03-26 | 1984-09-27 | Warner Lambert Co | |
| US4790881A (en) * | 1982-03-26 | 1988-12-13 | Warner-Lambert Company | Molded hydrophilic polymer |
| DE3222476A1 (de) | 1982-06-15 | 1983-12-15 | Warner-Lambert Co., 07950 Morris Plains, N.J. | Magensaftresistente weichgelatinekapseln und verfahren zu ihrer herstellung |
| US4518433A (en) | 1982-11-08 | 1985-05-21 | Fmc Corporation | Enteric coating for pharmaceutical dosage forms |
| US4500453A (en) * | 1984-06-29 | 1985-02-19 | Dynagel Incorporated | Cross-linked protein composition using aluminum salts of acetic acid |
| US4816259A (en) * | 1987-02-12 | 1989-03-28 | Chase Chemical Company, L.P. | Process for coating gelatin capsules |
| US5194464A (en) * | 1988-09-27 | 1993-03-16 | Takeda Chemical Industries, Ltd. | Enteric film and preparatoin thereof |
| US6482516B1 (en) | 1993-07-20 | 2002-11-19 | Banner Pharmacaps, Inc. | Enrobed tablet |
| US5146730A (en) | 1989-09-20 | 1992-09-15 | Banner Gelatin Products Corp. | Film-enrobed unitary-core medicament and the like |
| US5330759A (en) | 1992-08-26 | 1994-07-19 | Sterling Winthrop Inc. | Enteric coated soft capsules and method of preparation thereof |
| AU7375598A (en) | 1997-05-09 | 1998-11-27 | Sage Pharmaceuticals, Inc. | Stable oral pharmaceutical dosage forms |
| US7122207B2 (en) * | 1998-05-22 | 2006-10-17 | Bristol-Myers Squibb Company | High drug load acid labile pharmaceutical composition |
| UA73092C2 (uk) * | 1998-07-17 | 2005-06-15 | Брістол-Майерс Сквібб Компані | Таблетка з ентеросолюбільним покриттям і спосіб її приготування |
| US6193999B1 (en) * | 1999-03-01 | 2001-02-27 | Banner Pharmacaps, Inc. | Gum acacia substituted soft gelatin capsules |
| DE19922537A1 (de) | 1999-05-10 | 2000-11-16 | Roland Bodmeier | Darreichungsform zur Applikation in Körperöffnungen |
| AU2878801A (en) | 1999-10-01 | 2001-05-10 | Natco Pharma Limited | An improved pharmaceutical composition and a process for its preparation |
| EP1184033A1 (en) | 2000-09-01 | 2002-03-06 | Warner-Lambert Company | Pectin film compositions |
| WO2004012701A2 (en) * | 2002-08-02 | 2004-02-12 | Scitech Centre | NOVEL pH DEPENDENT ROBUST ENTERIC POLYMERIC CONTAINER, AN IMPROVEMENT OVER EXISTING ENTERIC DOSAGE FORMS. |
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2003
- 2003-06-27 DK DK03742336.5T patent/DK1545475T3/da active
- 2003-06-27 JP JP2004541451A patent/JP5248739B2/ja not_active Expired - Lifetime
- 2003-06-27 PT PT141704924T patent/PT2772250T/pt unknown
- 2003-06-27 EP EP03742336.5A patent/EP1545475B1/en not_active Expired - Lifetime
- 2003-06-27 AU AU2003299191A patent/AU2003299191A1/en not_active Abandoned
- 2003-06-27 US US10/529,984 patent/US8685445B2/en active Active
- 2003-06-27 PT PT37423365T patent/PT1545475E/pt unknown
- 2003-06-27 HU HUE14170492A patent/HUE031650T2/en unknown
- 2003-06-27 SI SI200332504A patent/SI2772250T1/sl unknown
- 2003-06-27 ES ES14170492.4T patent/ES2609059T3/es not_active Expired - Lifetime
- 2003-06-27 EP EP14170492.4A patent/EP2772250B1/en not_active Expired - Lifetime
- 2003-06-27 CN CNA038235579A patent/CN1688294A/zh active Pending
- 2003-06-27 WO PCT/US2003/020579 patent/WO2004030658A1/en not_active Ceased
- 2003-06-27 DK DK14170492.4T patent/DK2772250T3/en active
- 2003-06-27 SI SI200332379T patent/SI1545475T1/sl unknown
- 2003-06-27 MX MXPA05003524A patent/MXPA05003524A/es active IP Right Grant
- 2003-06-27 CA CA2500663A patent/CA2500663C/en not_active Expired - Lifetime
- 2003-06-27 ES ES03742336.5T patent/ES2500316T3/es not_active Expired - Lifetime
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2014
- 2014-03-28 US US14/228,387 patent/US9433585B2/en not_active Expired - Fee Related
-
2016
- 2016-11-21 CY CY20161101198T patent/CY1118258T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SI1545475T1 (sl) | 2014-10-30 |
| ES2609059T3 (es) | 2017-04-18 |
| DK1545475T3 (da) | 2014-07-28 |
| EP1545475B1 (en) | 2014-07-16 |
| ES2500316T3 (es) | 2014-09-30 |
| US8685445B2 (en) | 2014-04-01 |
| EP2772250A1 (en) | 2014-09-03 |
| US20140348879A1 (en) | 2014-11-27 |
| DK2772250T3 (en) | 2016-12-05 |
| CY1118258T1 (el) | 2017-06-28 |
| WO2004030658A1 (en) | 2004-04-15 |
| SI2772250T1 (sl) | 2017-03-31 |
| PT2772250T (pt) | 2017-01-02 |
| HUE031650T2 (en) | 2017-07-28 |
| JP2006505542A (ja) | 2006-02-16 |
| MXPA05003524A (es) | 2005-10-04 |
| EP2772250B1 (en) | 2016-09-28 |
| CN1688294A (zh) | 2005-10-26 |
| JP5248739B2 (ja) | 2013-07-31 |
| PT1545475E (pt) | 2014-09-16 |
| EP1545475A1 (en) | 2005-06-29 |
| US20060165778A1 (en) | 2006-07-27 |
| CA2500663A1 (en) | 2004-04-15 |
| US9433585B2 (en) | 2016-09-06 |
| AU2003299191A1 (en) | 2004-04-23 |
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