CA2718753A1 - Nouvelles formulations pharmaceutiques orales a liberation controlee - Google Patents
Nouvelles formulations pharmaceutiques orales a liberation controlee Download PDFInfo
- Publication number
- CA2718753A1 CA2718753A1 CA2718753A CA2718753A CA2718753A1 CA 2718753 A1 CA2718753 A1 CA 2718753A1 CA 2718753 A CA2718753 A CA 2718753A CA 2718753 A CA2718753 A CA 2718753A CA 2718753 A1 CA2718753 A1 CA 2718753A1
- Authority
- CA
- Canada
- Prior art keywords
- layer
- controlled
- water
- tolterodine
- release
- 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.)
- Abandoned
Links
- 238000013270 controlled release Methods 0.000 title claims abstract description 70
- 239000008194 pharmaceutical composition Substances 0.000 title description 7
- 239000011324 bead Substances 0.000 claims abstract description 95
- 239000004480 active ingredient Substances 0.000 claims abstract description 60
- 229920000642 polymer Polymers 0.000 claims abstract description 30
- 229920003169 water-soluble polymer Polymers 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 10
- 239000002775 capsule Substances 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims description 58
- 229960004045 tolterodine Drugs 0.000 claims description 46
- BDIAUFOIMFAIPU-UHFFFAOYSA-N valepotriate Natural products CC(C)CC(=O)OC1C=C(C(=COC2OC(=O)CC(C)C)COC(C)=O)C2C11CO1 BDIAUFOIMFAIPU-UHFFFAOYSA-N 0.000 claims description 46
- OOGJQPCLVADCPB-HXUWFJFHSA-N tolterodine Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C)C=2)O)=CC=CC=C1 OOGJQPCLVADCPB-HXUWFJFHSA-N 0.000 claims description 44
- 238000009472 formulation Methods 0.000 claims description 25
- 229920003176 water-insoluble polymer Polymers 0.000 claims description 20
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims description 19
- 229940016286 microcrystalline cellulose Drugs 0.000 claims description 19
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims description 19
- 239000008108 microcrystalline cellulose Substances 0.000 claims description 19
- 239000000651 prodrug Chemical group 0.000 claims description 18
- 229940002612 prodrug Drugs 0.000 claims description 18
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 16
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 16
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 16
- 239000001856 Ethyl cellulose Substances 0.000 claims description 14
- 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 claims description 14
- 229920001249 ethyl cellulose Polymers 0.000 claims description 14
- 235000019325 ethyl cellulose Nutrition 0.000 claims description 14
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 9
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 9
- 229940069328 povidone Drugs 0.000 claims description 9
- 229920003086 cellulose ether Polymers 0.000 claims description 8
- 229920001531 copovidone Polymers 0.000 claims description 8
- 235000010980 cellulose Nutrition 0.000 claims description 6
- 229920002678 cellulose Polymers 0.000 claims description 6
- 239000001913 cellulose Substances 0.000 claims description 6
- 229920001577 copolymer Polymers 0.000 claims description 6
- 239000006185 dispersion Substances 0.000 claims description 6
- 238000000338 in vitro Methods 0.000 claims description 4
- 238000009506 drug dissolution testing Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 16
- 239000000463 material Substances 0.000 abstract description 15
- 239000002552 dosage form Substances 0.000 abstract description 2
- 239000003814 drug Substances 0.000 description 35
- 229940079593 drug Drugs 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 239000008213 purified water Substances 0.000 description 22
- 239000012530 fluid Substances 0.000 description 13
- 238000000576 coating method Methods 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 11
- 238000004090 dissolution Methods 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 239000007921 spray Substances 0.000 description 9
- 239000002207 metabolite Substances 0.000 description 7
- TWHNMSJGYKMTRB-KXYUELECSA-N (2r,3r)-2,3-dihydroxybutanedioic acid;2-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-methylphenol Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C)C=2)O)=CC=CC=C1 TWHNMSJGYKMTRB-KXYUELECSA-N 0.000 description 6
- 229920003114 HPC-L Polymers 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 4
- 229960000935 dehydrated alcohol Drugs 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000001069 triethyl citrate Substances 0.000 description 4
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 4
- 235000013769 triethyl citrate Nutrition 0.000 description 4
- 230000008901 benefit Effects 0.000 description 3
- 239000012876 carrier material Substances 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 229920001477 hydrophilic polymer Polymers 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000008363 phosphate buffer Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 229940105356 tolterodine tartrate 4 mg Drugs 0.000 description 3
- YYSCJLLOWOUSHH-UHFFFAOYSA-N 4,4'-disulfanyldibutanoic acid Chemical compound OC(=O)CCCSSCCCC(O)=O YYSCJLLOWOUSHH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229940127022 high-dose drug Drugs 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229960003553 tolterodine tartrate Drugs 0.000 description 2
- 230000001131 transforming effect Effects 0.000 description 2
- DUXZAXCGJSBGDW-FQEVSTJZSA-N 2-[(1s)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-(hydroxymethyl)phenol Chemical compound C1([C@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(CO)C=2)O)=CC=CC=C1 DUXZAXCGJSBGDW-FQEVSTJZSA-N 0.000 description 1
- OOGJQPCLVADCPB-FQEVSTJZSA-N 2-[(1s)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-methylphenol Chemical compound C1([C@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C)C=2)O)=CC=CC=C1 OOGJQPCLVADCPB-FQEVSTJZSA-N 0.000 description 1
- DUXZAXCGJSBGDW-HXUWFJFHSA-N Desfesoterodine Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(CO)C=2)O)=CC=CC=C1 DUXZAXCGJSBGDW-HXUWFJFHSA-N 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000012738 dissolution medium Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 229960003883 furosemide Drugs 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000002536 noncholinergic effect Effects 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
Classifications
-
- 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
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
- A61K9/2077—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets
- A61K9/2081—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets with microcapsules or coated microparticles according to A61K9/50
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5073—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings
- A61K9/5078—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings with drug-free core
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Emergency Medicine (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
La présente invention concerne une bille à libération contrôlée contenant un principe pharmaceutiquement actif. La bille à libération contrôlée comprend un noyau constitué dun matériau inerte sensiblement insoluble dans leau. Une première couche est placée sur le noyau, la première couche comprenant un polymère sensiblement hydrosoluble. Une deuxième couche est placée sur la première couche, la deuxième couche comprenant le principe pharmaceutiquement actif et un polymère. Enfin, une troisième couche est placée sur la deuxième couche, la troisième couche comprenant un système polymère de contrôle de la libération. La présente invention concerne également des formes pharmaceutiques, telles que des comprimés et des gélules, comprenant les billes à libération contrôlée, et des procédés de fabrication des billes à libération contrôlée.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2718753A CA2718753A1 (fr) | 2008-04-01 | 2009-04-01 | Nouvelles formulations pharmaceutiques orales a liberation controlee |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2,629,099 | 2008-04-01 | ||
| CA002629099A CA2629099A1 (fr) | 2008-04-01 | 2008-04-01 | Nouvelles formulations pharmaceutiques orales a liberation controlee |
| PCT/CA2009/000418 WO2009121178A1 (fr) | 2008-04-01 | 2009-04-01 | Nouvelles formulations pharmaceutiques orales à libération contrôlée |
| CA2718753A CA2718753A1 (fr) | 2008-04-01 | 2009-04-01 | Nouvelles formulations pharmaceutiques orales a liberation controlee |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2718753A1 true CA2718753A1 (fr) | 2009-10-08 |
Family
ID=41134776
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002629099A Abandoned CA2629099A1 (fr) | 2008-04-01 | 2008-04-01 | Nouvelles formulations pharmaceutiques orales a liberation controlee |
| CA2718753A Abandoned CA2718753A1 (fr) | 2008-04-01 | 2009-04-01 | Nouvelles formulations pharmaceutiques orales a liberation controlee |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002629099A Abandoned CA2629099A1 (fr) | 2008-04-01 | 2008-04-01 | Nouvelles formulations pharmaceutiques orales a liberation controlee |
Country Status (2)
| Country | Link |
|---|---|
| CA (2) | CA2629099A1 (fr) |
| WO (1) | WO2009121178A1 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9078830B2 (en) | 2009-07-31 | 2015-07-14 | Ranbaxy Laboratories Limited | Multi-layered, multiple unit pharmaceutical compositions |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009019599A2 (fr) | 2007-08-08 | 2009-02-12 | Themis Laboratories Private Limited | Compositions à libération prolongée comprenant de la toltérodine |
| US20150086626A1 (en) * | 2012-04-17 | 2015-03-26 | Mylan, Inc | Stable dosage forms of skeletal muscle relaxants with extended release coating |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9402422D0 (sv) * | 1994-07-08 | 1994-07-08 | Astra Ab | New beads for controlled release and a pharmaceutical preparation containing the same |
| SE9803871D0 (sv) * | 1998-11-11 | 1998-11-11 | Pharmacia & Upjohn Ab | Therapeutic method and formulation |
| WO2004105735A1 (fr) * | 2003-05-30 | 2004-12-09 | Ranbaxy Laboratories Limited | Compositions pharmaceutiques de tolterodine a liberation controlee et leurs procedes de preparation |
| WO2007122015A1 (fr) * | 2006-04-21 | 2007-11-01 | Synthon B.V. | Perles de tolterodine |
| US20090017111A1 (en) * | 2007-07-03 | 2009-01-15 | Van Den Heuvel Dennie J M | Tolterodine bead |
-
2008
- 2008-04-01 CA CA002629099A patent/CA2629099A1/fr not_active Abandoned
-
2009
- 2009-04-01 CA CA2718753A patent/CA2718753A1/fr not_active Abandoned
- 2009-04-01 WO PCT/CA2009/000418 patent/WO2009121178A1/fr active Application Filing
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9078830B2 (en) | 2009-07-31 | 2015-07-14 | Ranbaxy Laboratories Limited | Multi-layered, multiple unit pharmaceutical compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2629099A1 (fr) | 2009-10-01 |
| WO2009121178A1 (fr) | 2009-10-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20140228 |
|
| FZDE | Discontinued |
Effective date: 20170403 |
|
| FZDE | Discontinued |
Effective date: 20170403 |