ZA200403928B - Pharmaceutical containing 3-(3-dimethylamino-1-ethyl-2-methyl-propyl)phenol and providing delayed release of the active ingredient - Google Patents
Pharmaceutical containing 3-(3-dimethylamino-1-ethyl-2-methyl-propyl)phenol and providing delayed release of the active ingredient Download PDFInfo
- Publication number
- ZA200403928B ZA200403928B ZA2004/03928A ZA200403928A ZA200403928B ZA 200403928 B ZA200403928 B ZA 200403928B ZA 2004/03928 A ZA2004/03928 A ZA 2004/03928A ZA 200403928 A ZA200403928 A ZA 200403928A ZA 200403928 B ZA200403928 B ZA 200403928B
- Authority
- ZA
- South Africa
- Prior art keywords
- weight
- ethyl
- methyl
- dimethylamino
- propyl
- Prior art date
Links
- 239000004480 active ingredient Substances 0.000 title claims description 93
- KWTWDQCKEHXFFR-UHFFFAOYSA-N 3-[1-(dimethylamino)-2-methylpentan-3-yl]phenol Chemical compound CN(C)CC(C)C(CC)C1=CC=CC(O)=C1 KWTWDQCKEHXFFR-UHFFFAOYSA-N 0.000 title claims description 41
- 230000003111 delayed effect Effects 0.000 title description 3
- 239000011159 matrix material Substances 0.000 claims description 63
- 239000008194 pharmaceutical composition Substances 0.000 claims description 40
- 239000003795 chemical substances by application Substances 0.000 claims description 30
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 24
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 18
- KWTWDQCKEHXFFR-SMDDNHRTSA-N tapentadol Chemical compound CN(C)C[C@H](C)[C@@H](CC)C1=CC=CC(O)=C1 KWTWDQCKEHXFFR-SMDDNHRTSA-N 0.000 claims description 12
- 238000000338 in vitro Methods 0.000 claims description 11
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 10
- 229920002678 cellulose Polymers 0.000 claims description 8
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 8
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 7
- 229920001477 hydrophilic polymer Polymers 0.000 claims description 7
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 229920003086 cellulose ether Polymers 0.000 claims description 6
- 229920001600 hydrophobic polymer Polymers 0.000 claims description 6
- KWTWDQCKEHXFFR-RISCZKNCSA-N 3-[(2s,3s)-1-(dimethylamino)-2-methylpentan-3-yl]phenol Chemical compound CN(C)C[C@@H](C)[C@H](CC)C1=CC=CC(O)=C1 KWTWDQCKEHXFFR-RISCZKNCSA-N 0.000 claims description 5
- 230000036470 plasma concentration Effects 0.000 claims description 4
- 238000001727 in vivo Methods 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 2
- 235000010944 ethyl methyl cellulose Nutrition 0.000 claims description 2
- 229920000609 methyl cellulose Polymers 0.000 claims description 2
- 235000010981 methylcellulose Nutrition 0.000 claims description 2
- 229920003087 methylethyl cellulose Polymers 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- 239000000203 mixture Substances 0.000 description 64
- 238000009472 formulation Methods 0.000 description 29
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 16
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 16
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 14
- 229940016286 microcrystalline cellulose Drugs 0.000 description 14
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 14
- 239000008108 microcrystalline cellulose Substances 0.000 description 14
- 239000002775 capsule Substances 0.000 description 12
- 238000000576 coating method Methods 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000011248 coating agent Substances 0.000 description 11
- 230000008569 process Effects 0.000 description 11
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
- 239000000377 silicon dioxide Substances 0.000 description 10
- 235000012239 silicon dioxide Nutrition 0.000 description 10
- 208000002193 Pain Diseases 0.000 description 8
- 230000000202 analgesic effect Effects 0.000 description 8
- ZELFLGGRLLOERW-YECZQDJWSA-N 3-[(2r,3r)-1-(dimethylamino)-2-methylpentan-3-yl]phenol;hydrochloride Chemical compound Cl.CN(C)C[C@H](C)[C@@H](CC)C1=CC=CC(O)=C1 ZELFLGGRLLOERW-YECZQDJWSA-N 0.000 description 7
- 239000000945 filler Substances 0.000 description 7
- 229920003084 Avicel® PH-102 Polymers 0.000 description 6
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 6
- 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 5
- 239000006185 dispersion Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 239000012729 immediate-release (IR) formulation Substances 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000008101 lactose Substances 0.000 description 5
- 229960001375 lactose Drugs 0.000 description 5
- 235000019359 magnesium stearate Nutrition 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000008188 pellet Substances 0.000 description 5
- 210000002381 plasma Anatomy 0.000 description 5
- 239000008298 dragée Substances 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 210000001035 gastrointestinal tract Anatomy 0.000 description 4
- -1 hydroxypropyl Chemical group 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000012216 screening Methods 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- 229910002012 Aerosil® Inorganic materials 0.000 description 2
- 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 2
- 241001440269 Cutina Species 0.000 description 2
- 239000001856 Ethyl cellulose Substances 0.000 description 2
- 241000275031 Nica Species 0.000 description 2
- 229920003110 Primojel Polymers 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 235000019700 dicalcium phosphate Nutrition 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229920001249 ethyl cellulose Polymers 0.000 description 2
- 235000019325 ethyl cellulose Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229960001021 lactose monohydrate Drugs 0.000 description 2
- 230000005923 long-lasting effect Effects 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920000193 polymethacrylate Polymers 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 238000004088 simulation Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- AYTRQOLWFRRPKZ-UHFFFAOYSA-N 3-[1-(dimethylamino)-2-methylpentan-3-yl]phenol;lead Chemical compound [Pb].CN(C)CC(C)C(CC)C1=CC=CC(O)=C1 AYTRQOLWFRRPKZ-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound 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 GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 208000000094 Chronic Pain Diseases 0.000 description 1
- 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 1
- 229920003134 Eudragit® polymer Polymers 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 101000921780 Solanum tuberosum Cysteine synthase Proteins 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000012738 dissolution medium Substances 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000010579 first pass effect Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229940031703 low substituted hydroxypropyl cellulose Drugs 0.000 description 1
- 230000002879 macerating effect Effects 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229940043348 myristyl alcohol Drugs 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000012430 stability testing Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229940012831 stearyl alcohol Drugs 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 238000005550 wet granulation Methods 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
- A61K9/20—Pills, tablets, discs, rods
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/136—Amines having aromatic rings, e.g. ketamine, nortriptyline having the amino group directly attached to the aromatic ring, e.g. benzeneamine
-
- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- 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
- A61K9/5005—Wall or coating material
- A61K9/5021—Organic macromolecular compounds
- A61K9/5036—Polysaccharides, e.g. gums, alginate; Cyclodextrin
- A61K9/5042—Cellulose; Cellulose derivatives, e.g. phthalate or acetate succinate esters of hydroxypropyl methylcellulose
- A61K9/5047—Cellulose ethers containing no ester groups, e.g. hydroxypropyl methylcellulose
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Emergency Medicine (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Nutrition Science (AREA)
- Physiology (AREA)
- Rheumatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10152469A DE10152469A1 (de) | 2001-10-24 | 2001-10-24 | 3-(3-Dimethylamino-1-ethyl-2-methyl-propyl)phenol enthaltendes Arzneimittel mit verzögerter Wirkstofffreisetzung |
| DE2002148309 DE10248309A1 (de) | 2002-10-16 | 2002-10-16 | 3-(3- Dimethylamino-1-ethyl-2-methyl-propyl) phenol enthaltendes Arzeimittel mit verzögerter Wirkstofffreisetzung |
| PCT/EP2002/011809 WO2003035053A1 (de) | 2001-10-24 | 2002-10-22 | 3-(3-dimethylamino-1-ethyl-2-methyl-propyl)phenol enthaltendes arzneimittel mit verzögerter wirkstofffreisetzung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200403928B true ZA200403928B (en) | 2005-07-27 |
Family
ID=26010444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA2004/03928A ZA200403928B (en) | 2001-10-24 | 2004-05-20 | Pharmaceutical containing 3-(3-dimethylamino-1-ethyl-2-methyl-propyl)phenol and providing delayed release of the active ingredient |
Country Status (28)
| Country | Link |
|---|---|
| US (7) | US20050058706A1 (https=) |
| EP (1) | EP1439829B1 (https=) |
| JP (2) | JP4758064B2 (https=) |
| KR (1) | KR100958045B1 (https=) |
| CN (1) | CN100402021C (https=) |
| AR (1) | AR036943A1 (https=) |
| AT (1) | ATE303802T1 (https=) |
| AU (1) | AU2002349001C1 (https=) |
| BR (1) | BRPI0213653B8 (https=) |
| CA (1) | CA2464578C (https=) |
| CO (1) | CO5570662A2 (https=) |
| CY (1) | CY2012022I2 (https=) |
| DE (1) | DE50204198D1 (https=) |
| DK (1) | DK1439829T3 (https=) |
| EC (1) | ECSP045102A (https=) |
| ES (1) | ES2248622T3 (https=) |
| HU (1) | HU230161B1 (https=) |
| IL (2) | IL161587A0 (https=) |
| MX (1) | MXPA04003742A (https=) |
| MY (1) | MY127797A (https=) |
| NO (2) | NO331896B1 (https=) |
| NZ (1) | NZ532999A (https=) |
| PE (1) | PE20030527A1 (https=) |
| PL (1) | PL216535B1 (https=) |
| PT (1) | PT1439829E (https=) |
| SI (1) | SI1439829T1 (https=) |
| WO (2) | WO2003035053A1 (https=) |
| ZA (1) | ZA200403928B (https=) |
Families Citing this family (78)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7776314B2 (en) | 2002-06-17 | 2010-08-17 | Grunenthal Gmbh | Abuse-proofed dosage system |
| PT1562567T (pt) | 2002-11-22 | 2017-08-24 | Gruenenthal Gmbh | Combinação de analgésicos selecionados e inibidores da cox-ii |
| DE102004020220A1 (de) * | 2004-04-22 | 2005-11-10 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten, festen Darreichungsform |
| DE102004032051A1 (de) | 2004-07-01 | 2006-01-19 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten, festen Darreichungsform |
| US20070048228A1 (en) | 2003-08-06 | 2007-03-01 | Elisabeth Arkenau-Maric | Abuse-proofed dosage form |
| DE10336400A1 (de) | 2003-08-06 | 2005-03-24 | Grünenthal GmbH | Gegen Missbrauch gesicherte Darreichungsform |
| US8075872B2 (en) | 2003-08-06 | 2011-12-13 | Gruenenthal Gmbh | Abuse-proofed dosage form |
| DE102005005446A1 (de) * | 2005-02-04 | 2006-08-10 | Grünenthal GmbH | Bruchfeste Darreichungsformen mit retardierter Freisetzung |
| DE10361596A1 (de) | 2003-12-24 | 2005-09-29 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform |
| NZ545202A (en) * | 2003-08-06 | 2010-03-26 | Gruenenthal Chemie | Abuse-proofed dosage form comprising opiods and a high molecular weight polyethylene oxide |
| DE602004007905T2 (de) * | 2004-06-28 | 2008-05-08 | Grünenthal GmbH | Kristalline Formen von (-)-(1R,2R)-3-(3-Dimethylamino-1-ethyl-2-methylpropyl)-phenol hydrochlorid |
| DE102004032049A1 (de) | 2004-07-01 | 2006-01-19 | Grünenthal GmbH | Gegen Missbrauch gesicherte, orale Darreichungsform |
| BRPI0513300B1 (pt) * | 2004-07-01 | 2018-11-06 | Gruenenthal Gmbh | forma farmacêutica oral, protegida frente ao abuso, contendo (1r, 2r)-3-(3-dimetilamino-1-etil-2- metil-lpropil)-fenol |
| DE102004032103A1 (de) * | 2004-07-01 | 2006-01-19 | Grünenthal GmbH | Gegen Missbrauch gesicherte, orale Darreichungsform |
| DE102005005449A1 (de) * | 2005-02-04 | 2006-08-10 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform |
| RU2442576C2 (ru) * | 2006-04-28 | 2012-02-20 | Грюненталь Гмбх | Фармацевтическая комбинация, содержащая 3-(3-диметиламино-1-этил-2-метилпропил)фенол и парацетамол |
| CN105561311B (zh) * | 2006-04-28 | 2019-07-16 | 格吕伦塔尔有限公司 | 包含3-(3-二甲基氨基-1-乙基-2-甲基-丙基)-苯酚和nsaid的药物组合物 |
| CN101091725A (zh) * | 2006-06-23 | 2007-12-26 | 天津天士力制药股份有限公司 | 一种中药颗粒及其制备方法 |
| SA07280459B1 (ar) | 2006-08-25 | 2011-07-20 | بيورديو فارما إل. بي. | أشكال جرعة صيدلانية للتناول عن طريق الفم مقاومة للعبث تشتمل على مسكن شبه أفيوني |
| DE102007011485A1 (de) * | 2007-03-07 | 2008-09-11 | Grünenthal GmbH | Darreichungsform mit erschwertem Missbrauch |
| EP1985292A1 (en) * | 2007-04-23 | 2008-10-29 | Grünenthal GmbH | Titration of tapentadol |
| DE102007019417A1 (de) | 2007-04-23 | 2008-11-13 | Grünenthal GmbH | Tapentadol zur Schmerzbehandlung bei Arthrose |
| CN102908339A (zh) * | 2007-11-23 | 2013-02-06 | 格吕伦塔尔有限公司 | 他喷他多组合物 |
| WO2009071310A1 (de) * | 2007-12-07 | 2009-06-11 | Grünenthal GmbH | Kristalline modifikationen von (1r,2r)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol |
| KR101616246B1 (ko) | 2008-01-25 | 2016-05-02 | 그뤼넨탈 게엠베하 | 약제학적 투여형 |
| AU2009243681B2 (en) | 2008-05-09 | 2013-12-19 | Grunenthal Gmbh | Process for the preparation of an intermediate powder formulation and a final solid dosage form under usage of a spray congealing step |
| US20100190752A1 (en) | 2008-09-05 | 2010-07-29 | Gruenenthal Gmbh | Pharmaceutical Combination |
| BRPI0921725A2 (pt) | 2008-10-30 | 2016-01-05 | Grüenthal GmbH | formas de dosagem potentes do tapentadol |
| WO2011009602A1 (en) | 2009-07-22 | 2011-01-27 | Grünenthal GmbH | Hot-melt extruded controlled release dosage form |
| TWI473628B (zh) | 2009-07-22 | 2015-02-21 | 用於對氧化敏感之類鴉片藥劑之抗破壞劑型 | |
| US9579285B2 (en) * | 2010-02-03 | 2017-02-28 | Gruenenthal Gmbh | Preparation of a powdery pharmaceutical composition by means of an extruder |
| JP5905872B2 (ja) * | 2010-04-07 | 2016-04-20 | ルピン・リミテッド | タペンタドールの制御放出医薬組成物 |
| EP2566461A2 (de) * | 2010-05-05 | 2013-03-13 | Ratiopharm GmbH | Festes tapentadol in nicht-kristalliner form |
| SI2582366T1 (sl) * | 2010-06-15 | 2016-02-29 | Gruenenthal Gmbh | Farmacevtska kombinacija za zdravljenje bolečine |
| PL2588093T3 (pl) | 2010-06-30 | 2017-07-31 | Grünenthal GmbH | Tapentadol do zastosowania w leczeniu zespołu jelita drażliwego |
| EP3597628A1 (en) | 2010-07-23 | 2020-01-22 | Grünenthal GmbH | Salts or co-crystals of 3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol |
| WO2012028318A1 (en) | 2010-09-02 | 2012-03-08 | Grünenthal GmbH | Tamper resistant dosage form comprising an anionic polymer |
| CA2808219C (en) | 2010-09-02 | 2019-05-14 | Gruenenthal Gmbh | Tamper resistant dosage form comprising inorganic salt |
| CA2828635C (en) | 2011-03-04 | 2020-01-14 | Grunenthal Gmbh | Parenteral administration of tapentadol |
| KR101946790B1 (ko) | 2011-03-04 | 2019-02-13 | 그뤼넨탈 게엠베하 | 경구 투여를 위한 타펜타돌의 수성 약제학적 제형 |
| RS56692B1 (sr) | 2011-03-04 | 2018-03-30 | Gruenenthal Gmbh | Polučvrsta vodena farmaceutska kompozicija koja sadrži tapentadol |
| US20120309840A1 (en) | 2011-04-05 | 2012-12-06 | Gruenenthal Gmbh | Treatment of Pain Associated with Trigeminal Neuralgia |
| RS58064B1 (sr) | 2011-04-05 | 2019-02-28 | Gruenenthal Gmbh | Tapentadol za sprečavanje hronifikacije bola |
| LT3272343T (lt) | 2011-04-29 | 2020-05-11 | Grünenthal GmbH | Tapentadolis, skirtas depresijos ir nerimo prevencijai ir gydymui |
| EP2736501B1 (en) * | 2011-07-29 | 2017-12-20 | Grünenthal GmbH | Intrathecal or epidural administration of 3-[(1s,2s)-3-(dimethylamino)-1-ethyl-2-methylpropyl]phenol |
| ES2648129T3 (es) | 2011-07-29 | 2017-12-28 | Grünenthal GmbH | Pastilla a prueba de manipulación que proporciona una liberación inmediata de un medicamento |
| AU2012289764B2 (en) | 2011-07-29 | 2017-03-02 | Grünenthal GmbH | Tamper-resistant tablet providing immediate drug release |
| EP2606879A1 (en) | 2011-12-21 | 2013-06-26 | Hexal AG | Multiple unit pellet tablet formulation comprising an opioid |
| US20130225697A1 (en) | 2012-02-28 | 2013-08-29 | Grunenthal Gmbh | Tamper-resistant dosage form comprising pharmacologically active compound and anionic polymer |
| PL2838512T3 (pl) | 2012-04-18 | 2018-12-31 | Grünenthal GmbH | Farmaceutyczna postać dawkowania odporna na niewłaściwe użycie i odporna na uderzeniowe uwalnianie dawki |
| US10064945B2 (en) | 2012-05-11 | 2018-09-04 | Gruenenthal Gmbh | Thermoformed, tamper-resistant pharmaceutical dosage form containing zinc |
| JP6466417B2 (ja) | 2013-05-29 | 2019-02-06 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 二峰性放出プロファイルを有する改変防止（ｔａｍｐｅｒ−ｒｅｓｉｓｔａｎｔ）剤形 |
| AU2014273227B2 (en) | 2013-05-29 | 2019-08-15 | Grunenthal Gmbh | Tamper-resistant dosage form containing one or more particles |
| EP2808319A1 (en) | 2013-05-31 | 2014-12-03 | Arevipharma GmbH | 3-[3-(Dimethylamino)-1-ethyl-2-methylpropyl]phenol resin complex |
| JP6449871B2 (ja) | 2013-07-12 | 2019-01-09 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | エチレン−酢酸ビニルポリマーを含有する改変防止剤形 |
| EP2845625A1 (en) | 2013-09-04 | 2015-03-11 | Grünenthal GmbH | Tapentadol for use in the treatment of fibromyalgia and chronic fatigue syndrome |
| WO2015071248A1 (en) | 2013-11-15 | 2015-05-21 | Synthon B.V. | Abuse-proofed extended release pharmaceutical composition comprising tapentadol |
| EP3073994A1 (en) | 2013-11-26 | 2016-10-05 | Grünenthal GmbH | Preparation of a powdery pharmaceutical composition by means of cryo-milling |
| EP2942054A1 (en) * | 2014-05-09 | 2015-11-11 | G.L. Pharma GmbH | Slow-release pharmaceutical formulation |
| EP3142646A1 (en) | 2014-05-12 | 2017-03-22 | Grünenthal GmbH | Tamper resistant immediate release capsule formulation comprising tapentadol |
| EA201692388A1 (ru) | 2014-05-26 | 2017-05-31 | Грюненталь Гмбх | Лекарственная форма в виде множества частиц, защищенная от вызываемого этанолом сброса дозы |
| EP3273953B1 (en) | 2015-03-27 | 2019-01-02 | Grünenthal GmbH | Stable formulation for parenteral administration of tapentadol |
| BR112017021475A2 (pt) | 2015-04-24 | 2018-07-10 | Gruenenthal Gmbh | forma de dosagem resistente à adulteração (tamper) com liberação imediata e resistência contra extração de solvente |
| WO2017042325A1 (en) | 2015-09-10 | 2017-03-16 | Grünenthal GmbH | Protecting oral overdose with abuse deterrent immediate release formulations |
| EP3231420A1 (en) | 2016-02-29 | 2017-10-18 | G.L. Pharma GmbH | Abuse-deterrent pharmaceutical compositions |
| CN109996533A (zh) | 2016-09-23 | 2019-07-09 | 格吕伦塔尔有限公司 | 用于肠胃外施用他喷他多的稳定制剂 |
| WO2018153947A1 (en) | 2017-02-23 | 2018-08-30 | Grünenthal GmbH | Tapentadol as local anesthetic |
| US20180369151A1 (en) * | 2017-05-29 | 2018-12-27 | Grünenthal GmbH | Multiparticulate oral dosage form providing prolonged release of tapentadol |
| PE20230105A1 (es) | 2020-03-02 | 2023-01-25 | Gruenenthal Chemie | Forma de dosificacion que proporciona liberacion prolongada de sal de acido fosforico de tapentadol |
| EP3875079A1 (en) | 2020-03-02 | 2021-09-08 | Grünenthal GmbH | Dosage form providing prolonged release of tapentadol phosphoric acid salt |
| PL3875077T3 (pl) * | 2020-03-02 | 2024-03-11 | Grünenthal GmbH | Postać dawkowania zapewniająca przedłużone uwalnianie soli kwasu fosforowego tapentadolu |
| ES3060121T3 (en) * | 2020-03-02 | 2026-03-25 | Gruenenthal Gmbh | Dosage form providing prolonged release of tapentadol phosphoric acid salt |
| AU2020100442B4 (en) * | 2020-03-02 | 2020-06-18 | Grünenthal GmbH | Dosage form providing prolonged release of tapentadol phosphoric acid salt |
| ES3010208T3 (en) * | 2020-03-16 | 2025-04-01 | Gruenenthal Gmbh | Scored tablet comprising tapentadol |
| DE202020104285U1 (de) | 2020-07-24 | 2020-12-18 | Grünenthal GmbH | Ethylcellulose-beschichtete Partikel enthaltend ein Salz aus Tapentadol und Phosphorsäure |
| HUE059465T2 (hu) * | 2020-11-10 | 2022-11-28 | Gruenenthal Gmbh | A tapentadol L-(+)- borkõsav-só késleltetett felszabadulású adagolási formája |
| PE20240113A1 (es) | 2020-11-10 | 2024-01-22 | Gruenenthal Chemie | Formas de dosificacion de liberacion sostenida de una sal de tapentadol con acido l-(+)-tartarico |
| DE202020005470U1 (de) | 2020-11-10 | 2022-01-25 | Grünenthal GmbH | Darreichungsformen mit verlängerter Freisetzung eines Salzes von Tapentadol mit L-(+)-Weinsäure |
Family Cites Families (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3870790A (en) * | 1970-01-22 | 1975-03-11 | Forest Laboratories | Solid pharmaceutical formulations containing hydroxypropyl methyl cellulose |
| DE2117239A1 (de) | 1971-04-08 | 1972-11-16 | König, Wilhelm, 4712 Werne | Verfahren zum Erstellen von Wänden aus Schalungssteinen |
| US4126672A (en) * | 1976-02-04 | 1978-11-21 | Hoffmann-La Roche Inc. | Sustained release pharmaceutical capsules |
| US4389393A (en) | 1982-03-26 | 1983-06-21 | Forest Laboratories, Inc. | Sustained release therapeutic compositions based on high molecular weight hydroxypropylmethylcellulose |
| US4443428A (en) * | 1982-06-21 | 1984-04-17 | Euroceltique, S.A. | Extended action controlled release compositions |
| US5641631A (en) | 1983-01-10 | 1997-06-24 | Gen-Probe Incorporated | Method for detecting, identifying, and quantitating organisms and viruses |
| US4783337A (en) * | 1983-05-11 | 1988-11-08 | Alza Corporation | Osmotic system comprising plurality of members for dispensing drug |
| US4612008A (en) * | 1983-05-11 | 1986-09-16 | Alza Corporation | Osmotic device with dual thermodynamic activity |
| US4765989A (en) * | 1983-05-11 | 1988-08-23 | Alza Corporation | Osmotic device for administering certain drugs |
| GB8519310D0 (en) | 1985-07-31 | 1985-09-04 | Zyma Sa | Granular active substances |
| GB8626098D0 (en) * | 1986-10-31 | 1986-12-03 | Euro Celtique Sa | Controlled release hydromorphone composition |
| US5126145A (en) * | 1989-04-13 | 1992-06-30 | Upsher Smith Laboratories Inc | Controlled release tablet containing water soluble medicament |
| US5266331A (en) * | 1991-11-27 | 1993-11-30 | Euroceltique, S.A. | Controlled release oxycodone compositions |
| US5286493A (en) * | 1992-01-27 | 1994-02-15 | Euroceltique, S.A. | Stabilized controlled release formulations having acrylic polymer coating |
| US5478577A (en) * | 1993-11-23 | 1995-12-26 | Euroceltique, S.A. | Method of treating pain by administering 24 hour oral opioid formulations exhibiting rapid rate of initial rise of plasma drug level |
| JP3140465B2 (ja) * | 1992-09-18 | 2001-03-05 | 山之内製薬株式会社 | ハイドロゲル徐放性製剤 |
| NZ260408A (en) | 1993-05-10 | 1996-05-28 | Euro Celtique Sa | Controlled release preparation comprising tramadol |
| IL110014A (en) * | 1993-07-01 | 1999-11-30 | Euro Celtique Sa | Solid controlled-release oral dosage forms of opioid analgesics |
| DE4329794C2 (de) * | 1993-09-03 | 1997-09-18 | Gruenenthal Gmbh | Tramadolsalz enthaltende Arzneimittel mit verzögerter Wirkstofffreisetzung |
| CA2149408C (en) | 1993-11-17 | 2008-04-01 | Kinuko Oku | Compositions for curing affected abnormal tissues, method for the preparation thereof, and usage thereof |
| US5891471A (en) * | 1993-11-23 | 1999-04-06 | Euro-Celtique, S.A. | Pharmaceutical multiparticulates |
| US5843480A (en) * | 1994-03-14 | 1998-12-01 | Euro-Celtique, S.A. | Controlled release diamorphine formulation |
| DE4426245A1 (de) * | 1994-07-23 | 1996-02-22 | Gruenenthal Gmbh | 1-Phenyl-3-dimethylamino-propanverbindungen mit pharmakologischer Wirkung |
| US5478572A (en) * | 1994-09-06 | 1995-12-26 | Bristol-Myers Squibb Co. | Gepirone dosage form |
| CN1125572A (zh) * | 1994-12-28 | 1996-07-03 | 顺德市广容制药厂 | 一种罗通定痛释片的制作方法 |
| IL116674A (en) * | 1995-01-09 | 2003-05-29 | Mendell Co Inc Edward | Microcrystalline cellulose-based excipient having improved compressibility, pharmaceutical compositions containing the same and methods for the preparation of said excipient and of solid dosage form thereof |
| DE19525137C2 (de) | 1995-07-11 | 2003-02-27 | Gruenenthal Gmbh | 6-Dimethylaminomethyl-1-phenyl-cyclohexanverbin -dungen als Zwischenprodukte zur Herstellung pharmazeutischer Wirkstoffe |
| DE19609847A1 (de) | 1996-03-13 | 1997-09-18 | Gruenenthal Gmbh | Dimethyl-(3-aryl-but-3-enyl)-aminverbindungen als pharmazeutische Wirkstoffe |
| US6096339A (en) | 1997-04-04 | 2000-08-01 | Alza Corporation | Dosage form, process of making and using same |
| IL123505A (en) * | 1996-07-08 | 2004-12-15 | Penwest Pharmaceuticals Compan | Sustained release matrix for high-dose insoluble drugs |
| DE19630035A1 (de) | 1996-07-25 | 1998-01-29 | Asta Medica Ag | Tramadol Multiple Unit Formulierungen |
| CA2290624C (en) * | 1997-06-06 | 2006-12-05 | John W. Shell | Gastric-retentive oral drug dosage forms for controlled release of highly soluble drugs |
| US6245357B1 (en) * | 1998-03-06 | 2001-06-12 | Alza Corporation | Extended release dosage form |
| US6106862A (en) * | 1998-08-13 | 2000-08-22 | Andrx Corporation | Once daily analgesic tablet |
| DE19901683B4 (de) | 1999-01-18 | 2005-07-21 | Grünenthal GmbH | Analgetikum mit kontrollierter Wirkstofffreisetzung |
| AU764453B2 (en) * | 1999-10-29 | 2003-08-21 | Euro-Celtique S.A. | Controlled release hydrocodone formulations |
| DE10109763A1 (de) | 2001-02-28 | 2002-09-05 | Gruenenthal Gmbh | Pharmazeutische Salze |
| DE10248309A1 (de) | 2002-10-16 | 2004-04-29 | Grünenthal GmbH | 3-(3- Dimethylamino-1-ethyl-2-methyl-propyl) phenol enthaltendes Arzeimittel mit verzögerter Wirkstofffreisetzung |
-
2002
- 2002-10-18 PE PE2002001030A patent/PE20030527A1/es active IP Right Grant
- 2002-10-22 ES ES02781278T patent/ES2248622T3/es not_active Expired - Lifetime
- 2002-10-22 WO PCT/EP2002/011809 patent/WO2003035053A1/de not_active Ceased
- 2002-10-22 PL PL369756A patent/PL216535B1/pl unknown
- 2002-10-22 HU HU0402104A patent/HU230161B1/hu unknown
- 2002-10-22 AT AT02781278T patent/ATE303802T1/de active
- 2002-10-22 MX MXPA04003742A patent/MXPA04003742A/es active IP Right Grant
- 2002-10-22 DK DK02781278T patent/DK1439829T3/da active
- 2002-10-22 NZ NZ532999A patent/NZ532999A/en not_active IP Right Cessation
- 2002-10-22 BR BRPI0213653A patent/BRPI0213653B8/pt active IP Right Grant
- 2002-10-22 DE DE50204198T patent/DE50204198D1/de not_active Expired - Lifetime
- 2002-10-22 CA CA2464578A patent/CA2464578C/en not_active Expired - Lifetime
- 2002-10-22 EP EP02781278A patent/EP1439829B1/de not_active Expired - Lifetime
- 2002-10-22 SI SI200230224T patent/SI1439829T1/sl unknown
- 2002-10-22 AU AU2002349001A patent/AU2002349001C1/en not_active Expired
- 2002-10-22 CN CNB028259769A patent/CN100402021C/zh not_active Expired - Lifetime
- 2002-10-22 WO PCT/EP2002/011806 patent/WO2003035054A1/de not_active Ceased
- 2002-10-22 IL IL16158702A patent/IL161587A0/xx unknown
- 2002-10-22 KR KR1020047006113A patent/KR100958045B1/ko not_active Expired - Lifetime
- 2002-10-22 JP JP2003537620A patent/JP4758064B2/ja not_active Expired - Lifetime
- 2002-10-22 PT PT02781278T patent/PT1439829E/pt unknown
- 2002-10-23 AR ARP020104010A patent/AR036943A1/es not_active Application Discontinuation
- 2002-10-24 MY MYPI20023979A patent/MY127797A/en unknown
-
2004
- 2004-04-22 IL IL161587A patent/IL161587A/en active IP Right Grant
- 2004-04-22 CO CO04037005A patent/CO5570662A2/es not_active Application Discontinuation
- 2004-04-26 US US10/831,368 patent/US20050058706A1/en not_active Abandoned
- 2004-05-11 NO NO20041924A patent/NO331896B1/no not_active IP Right Cessation
- 2004-05-12 EC EC2004005102A patent/ECSP045102A/es unknown
- 2004-05-20 ZA ZA2004/03928A patent/ZA200403928B/en unknown
-
2010
- 2010-08-05 JP JP2010176084A patent/JP2010280697A/ja active Pending
-
2011
- 2011-09-23 US US13/242,800 patent/US20120034304A1/en not_active Abandoned
-
2012
- 2012-05-08 NO NO2012007C patent/NO2012007I2/no unknown
- 2012-08-13 CY CY2012022C patent/CY2012022I2/el unknown
-
2013
- 2013-04-23 US US13/868,635 patent/US20130237608A1/en not_active Abandoned
-
2016
- 2016-02-08 US US15/018,529 patent/US20160151309A1/en not_active Abandoned
- 2016-12-13 US US15/377,628 patent/US20170087103A1/en not_active Abandoned
-
2018
- 2018-04-02 US US15/943,175 patent/US20180221308A1/en not_active Abandoned
-
2019
- 2019-10-14 US US16/600,974 patent/US11007156B2/en not_active Expired - Fee Related
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US11007156B2 (en) | Prolonged release pharmaceutical composition containing 3-(3-dimethylamino-1-ethyl-2-methyl-propyl)phenol | |
| US20090220593A1 (en) | Extended release dosage forms of quetiapine | |
| US20040197404A1 (en) | Extended release oral dosage form | |
| CA2739611C (en) | Pharmaceutical containing 3-(3-dimethylamino-1-ethyl-2-methyl-propyl)phenol and providing delayed release of the active ingredient | |
| US7410965B2 (en) | Delayed release pharmaceutical composition containing 1-dimethyl-amino-3-(3-methoxyphenyl)-2-methyl-pentan-3-ol | |
| AU2006291422B2 (en) | 3-(2-dimethylaminomethyl cyclohexyl) phenol retard formulation | |
| CA2488220C (en) | Medicament with delayed active constituent release containing 1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol | |
| WO2003017984A1 (en) | A new extended release oral dosage form | |
| HK1068539B (en) | Pharmaceutical containing 3-(3-dimethylamino-1-ethyl-2-methyl-propyl)phenol and providing delayed release of the active ingredient | |
| NZ531437A (en) | Extended release oral dosage form of a pharmaceutically active substance, (R)-3-N,N-dicyclobutylamino-8-fluoro-3,4-dihydro-2H-1-benzopyran-5-carboxamide | |
| AU2002327992A1 (en) | a new extended release oral dosage form |