IL126477A - Controlled Release Drugs Containing Amylose and Hydroxypropylmethylcellulose Based Substance - Google Patents
Controlled Release Drugs Containing Amylose and Hydroxypropylmethylcellulose Based SubstanceInfo
- Publication number
- IL126477A IL126477A IL12647797A IL12647797A IL126477A IL 126477 A IL126477 A IL 126477A IL 12647797 A IL12647797 A IL 12647797A IL 12647797 A IL12647797 A IL 12647797A IL 126477 A IL126477 A IL 126477A
- Authority
- IL
- Israel
- Prior art keywords
- hpmc
- tablet
- carrier
- cross
- amylose
- Prior art date
Links
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 title claims abstract description 90
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 title claims abstract description 88
- 229920000856 Amylose Polymers 0.000 title claims abstract description 46
- 238000013270 controlled release Methods 0.000 title claims abstract description 19
- 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 title claims description 86
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 title claims description 85
- 239000004480 active ingredient Substances 0.000 claims abstract description 40
- 102000004190 Enzymes Human genes 0.000 claims abstract description 24
- 108090000790 Enzymes Proteins 0.000 claims abstract description 24
- 230000000694 effects Effects 0.000 claims abstract description 11
- 239000002671 adjuvant Substances 0.000 claims abstract description 10
- 239000003431 cross linking reagent Substances 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 10
- 239000011159 matrix material Substances 0.000 claims description 7
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 5
- 230000000181 anti-adherent effect Effects 0.000 claims description 3
- -1 glidants Substances 0.000 claims description 3
- 239000004615 ingredient Substances 0.000 claims description 3
- 239000003911 antiadherent Substances 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 239000007884 disintegrant Substances 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- 239000000314 lubricant Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 229940088598 enzyme Drugs 0.000 abstract description 23
- 102000004139 alpha-Amylases Human genes 0.000 abstract description 5
- 108090000637 alpha-Amylases Proteins 0.000 abstract description 5
- 230000000968 intestinal effect Effects 0.000 abstract description 5
- 229940024171 alpha-amylase Drugs 0.000 abstract description 3
- 239000003826 tablet Substances 0.000 description 54
- TVYLLZQTGLZFBW-ZBFHGGJFSA-N (R,R)-tramadol Chemical compound COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-ZBFHGGJFSA-N 0.000 description 20
- 239000007891 compressed tablet Substances 0.000 description 17
- 239000002609 medium Substances 0.000 description 14
- 238000004090 dissolution Methods 0.000 description 11
- 230000002255 enzymatic effect Effects 0.000 description 10
- 239000008363 phosphate buffer Substances 0.000 description 9
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 4
- 239000000017 hydrogel Substances 0.000 description 4
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 4
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- QWVCIORZLNBIIC-UHFFFAOYSA-N 2,3-dibromopropan-1-ol Chemical compound OCC(Br)CBr QWVCIORZLNBIIC-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 229960001631 carbomer Drugs 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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
- 239000004382 Amylase Substances 0.000 description 1
- 102000013142 Amylases Human genes 0.000 description 1
- 108010065511 Amylases Proteins 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- 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 1
- 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 1
- 229920000715 Mucilage Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 235000019418 amylase Nutrition 0.000 description 1
- 229940069428 antacid Drugs 0.000 description 1
- 239000003159 antacid agent Substances 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 230000003474 anti-emetic effect Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 239000000924 antiasthmatic agent Substances 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 239000002111 antiemetic agent Substances 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 229940125716 antipyretic agent Drugs 0.000 description 1
- 229940124575 antispasmodic agent Drugs 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
- 239000000850 decongestant Substances 0.000 description 1
- 229940124581 decongestants Drugs 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 102000038379 digestive enzymes Human genes 0.000 description 1
- 108091007734 digestive enzymes Proteins 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 230000007515 enzymatic degradation Effects 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000012631 food intake Nutrition 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000003345 hyperglycaemic effect Effects 0.000 description 1
- 229940126904 hypoglycaemic agent Drugs 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- KWGRBVOPPLSCSI-WCBMZHEXSA-N pseudoephedrine Chemical compound CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WCBMZHEXSA-N 0.000 description 1
- 229960003908 pseudoephedrine Drugs 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent 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
- A61K9/20—Pills, tablets, discs, rods
-
- 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
- A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin
-
- 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
- A61K9/20—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
- A61K9/2086—Layered tablets, e.g. bilayer tablets; Tablets of the type inert core-active coat
- A61K9/209—Layered tablets, e.g. bilayer tablets; Tablets of the type inert core-active coat containing drug in at least two layers or in the core and in at least one outer layer
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002173818A CA2173818A1 (fr) | 1996-04-10 | 1996-04-10 | Comprime pharmaceutique a liberation controlee contenant un support a base d'amylose reticule et d'hydroxypropylmethylcellulose |
| PCT/CA1997/000229 WO1997037639A1 (fr) | 1996-04-10 | 1997-04-04 | Comprime pharmaceutique a liberation controlee contenant un support a base d'amylose reticule et d'hydroxypropylmethylcellulose |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL126477A0 IL126477A0 (en) | 1999-08-17 |
| IL126477A true IL126477A (en) | 2001-10-31 |
Family
ID=4157953
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL12647797A IL126477A (en) | 1996-04-10 | 1997-04-04 | Controlled Release Drugs Containing Amylose and Hydroxypropylmethylcellulose Based Substance |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US5885615A (xx) |
| EP (1) | EP0954290B1 (xx) |
| JP (1) | JP4166278B2 (xx) |
| KR (1) | KR100439614B1 (xx) |
| CN (1) | CN1218396A (xx) |
| AT (1) | ATE240719T1 (xx) |
| AU (1) | AU711089B2 (xx) |
| BR (1) | BR9708772A (xx) |
| CA (1) | CA2173818A1 (xx) |
| CZ (1) | CZ294342B6 (xx) |
| DE (1) | DE69722247T2 (xx) |
| DK (1) | DK0954290T3 (xx) |
| ES (1) | ES2200166T3 (xx) |
| IL (1) | IL126477A (xx) |
| MY (1) | MY115535A (xx) |
| NO (1) | NO321862B1 (xx) |
| NZ (1) | NZ332576A (xx) |
| PL (1) | PL187764B1 (xx) |
| PT (1) | PT954290E (xx) |
| TR (1) | TR199802034T2 (xx) |
| WO (1) | WO1997037639A1 (xx) |
| ZA (1) | ZA973054B (xx) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ260408A (en) | 1993-05-10 | 1996-05-28 | Euro Celtique Sa | Controlled release preparation comprising tramadol |
| US6197339B1 (en) * | 1997-09-30 | 2001-03-06 | Pharmacia & Upjohn Company | Sustained release tablet formulation to treat Parkinson's disease |
| US6284273B1 (en) * | 1998-02-24 | 2001-09-04 | Vincent Lenaerts | Cross-linked high amylose starch resistant to amylase as a matrix for the slow release of biologically active compounds |
| US6416786B1 (en) | 1998-12-11 | 2002-07-09 | Nostrum Pharmaceuticals, Inc. | Sustained release tablet containing hydrocolloid and cellulose ether |
| US6555139B2 (en) | 1999-06-28 | 2003-04-29 | Wockhardt Europe Limited | Preparation of micron-size pharmaceutical particles by microfluidization |
| EP1174127A1 (en) * | 2000-07-21 | 2002-01-23 | Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno | Composition for targeted release of an actvie substance and process for producing such a composition |
| WO2003017981A1 (en) * | 2001-08-29 | 2003-03-06 | Ranbaxy Laboratories Limited | Controlled release formulation of clarithromycin or tinidazol |
| ES2399880T3 (es) * | 2002-03-15 | 2013-04-04 | Cypress Bioscience, Inc. | Milnaciprán para el tratamiento del síndrome del intestino irritable |
| US20040132826A1 (en) * | 2002-10-25 | 2004-07-08 | Collegium Pharmaceutical, Inc. | Modified release compositions of milnacipran |
| US8487002B2 (en) * | 2002-10-25 | 2013-07-16 | Paladin Labs Inc. | Controlled-release compositions |
| TWI319713B (en) * | 2002-10-25 | 2010-01-21 | Sustained-release tramadol formulations with 24-hour efficacy | |
| US20060003004A1 (en) * | 2002-10-25 | 2006-01-05 | Collegium Pharmaceutical, Inc. | Pulsatile release compositions of milnacipran |
| RU2333745C2 (ru) * | 2002-10-25 | 2008-09-20 | Лабофарм Инк. | Композиции с контролируемым высвобождением |
| MY142195A (en) * | 2002-10-25 | 2010-10-15 | Labopharm Inc | Controlled-release compositions |
| WO2004047651A2 (en) * | 2002-11-25 | 2004-06-10 | Boston Scientific Limited | Injection device for treating mammalian body |
| WO2004067039A1 (en) * | 2003-01-28 | 2004-08-12 | Collegium Pharmaceutical, Inc. | Multiparticulate compositions of milnacipran for oral administration |
| US20060172006A1 (en) * | 2003-10-10 | 2006-08-03 | Vincent Lenaerts | Sustained-release tramadol formulations with 24-hour clinical efficacy |
| AR051654A1 (es) * | 2004-11-04 | 2007-01-31 | Astrazeneca Ab | Nuevas formulaciones de pellets de liberacion modificada para inhibidores de la bomba de protones |
| CA2491665A1 (fr) * | 2004-12-24 | 2006-06-24 | Louis Cartilier | Formulation de comprime pour liberation soutenue de principe actif |
| CN101242856A (zh) * | 2005-09-09 | 2008-08-13 | 莱博法姆公司 | 持续药物释放的组合物 |
| DK1931346T3 (da) * | 2005-09-09 | 2012-10-22 | Angelini Labopharm Llc | Trazodonsammensætning til indgivelse en gang om dagen |
| WO2007040557A1 (en) * | 2005-09-21 | 2007-04-12 | Surmodics, Inc. | Coatings and articles including natural biodegradable polysaccharides |
| WO2007038126A1 (en) * | 2005-09-21 | 2007-04-05 | Surmodics, Inc. | In vivo formed matrices including natural biodegradable polysaccharides and ophthalmic uses thereof |
| EP1946780B1 (en) * | 2005-11-11 | 2012-01-11 | Asahi Kasei Chemicals Corporation | Controlled release solid preparation |
| WO2008073295A2 (en) * | 2006-12-07 | 2008-06-19 | Surmodics, Inc. | Latent stabilization of bioactive agents releasable from implantable medical articles |
| CA2723192A1 (en) | 2008-05-07 | 2009-11-12 | Surmodics, Inc. | Delivery of nucleic acid complexes from particles |
| US20100056540A1 (en) * | 2008-09-04 | 2010-03-04 | Bristol-Myers Squibb Company | Stable pharmaceutical composition for optimized delivery of an hiv attachment inhibitor |
| CA2741751C (en) * | 2008-10-27 | 2017-05-09 | Alza Corporation | Extended release oral acetaminophen/tramadol dosage form |
| US20100260842A1 (en) * | 2009-04-06 | 2010-10-14 | Rashmi Nair | Pseudoephedrine pharmaceutical formulations |
| US8901092B2 (en) | 2010-12-29 | 2014-12-02 | Surmodics, Inc. | Functionalized polysaccharides for active agent delivery |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3065143A (en) * | 1960-04-19 | 1962-11-20 | Richardson Merrell Inc | Sustained release tablet |
| US4167558A (en) * | 1976-02-13 | 1979-09-11 | Hoffmann-La Roche Inc. | Novel sustained release tablet formulations |
| US4389393A (en) * | 1982-03-26 | 1983-06-21 | Forest Laboratories, Inc. | Sustained release therapeutic compositions based on high molecular weight hydroxypropylmethylcellulose |
| US4610870A (en) * | 1984-10-05 | 1986-09-09 | E. R. Squibb & Sons, Inc. | Controlled release formulation |
| US4734285A (en) * | 1985-10-28 | 1988-03-29 | The Dow Chemical Company | Sustained release compositions |
| US4704285A (en) * | 1985-11-18 | 1987-11-03 | The Dow Chemical Company | Sustained release compositions comprising hydroxypropyl cellulose ethers |
| US4775535A (en) * | 1986-04-04 | 1988-10-04 | Hans Lowey | Method of preparing controlled long-acting pharmaceutical formulations in unit dosage form having uniform and comparable bioavailability characteristics |
| US4855143A (en) * | 1986-04-04 | 1989-08-08 | Hans Lowey | Method of preparing controlled long-acting pharmaceutical formulations in unit dosage form having uniform and comparable bioavailability characteristics |
| US5603956A (en) * | 1990-11-27 | 1997-02-18 | Labopharm Inc. | Cross-linked enzymatically controlled drug release |
| CA2041774C (en) * | 1990-11-27 | 1994-04-19 | Mircea A. Mateescu | Use of cross-linked amylose as a matrix for the slow release of biologically active compounds |
| NL9201196A (nl) * | 1992-07-03 | 1994-02-01 | Tno | Preparaat voor de gereguleerde afgifte van een werkzame stof en werkwijze ter bereiding van een dergelijk preparaat. |
| RU2136270C1 (ru) * | 1992-07-24 | 1999-09-10 | Лабофарм Инк. | Твердая фармацевтическая форма |
| US5616343A (en) * | 1993-03-25 | 1997-04-01 | Labopharm, Inc. | Cross-linked amylose as a binder/disintegrant in tablets |
| IT1282650B1 (it) * | 1996-02-19 | 1998-03-31 | Jagotec Ag | Compressa farmaceutica,caratterizzata da elevato aumento di volume a contatto con liquidi biologici |
-
1996
- 1996-04-10 CA CA002173818A patent/CA2173818A1/fr not_active Abandoned
- 1996-08-19 US US08/699,611 patent/US5885615A/en not_active Expired - Lifetime
-
1997
- 1997-04-04 TR TR1998/02034T patent/TR199802034T2/xx unknown
- 1997-04-04 CN CN97194638A patent/CN1218396A/zh active Pending
- 1997-04-04 AT AT97915220T patent/ATE240719T1/de active
- 1997-04-04 DK DK97915220T patent/DK0954290T3/da active
- 1997-04-04 CZ CZ19983254A patent/CZ294342B6/cs not_active IP Right Cessation
- 1997-04-04 AU AU22832/97A patent/AU711089B2/en not_active Ceased
- 1997-04-04 JP JP53470597A patent/JP4166278B2/ja not_active Expired - Fee Related
- 1997-04-04 ES ES97915220T patent/ES2200166T3/es not_active Expired - Lifetime
- 1997-04-04 EP EP97915220A patent/EP0954290B1/fr not_active Expired - Lifetime
- 1997-04-04 BR BR9708772-6A patent/BR9708772A/pt not_active IP Right Cessation
- 1997-04-04 IL IL12647797A patent/IL126477A/en not_active IP Right Cessation
- 1997-04-04 WO PCT/CA1997/000229 patent/WO1997037639A1/fr not_active Ceased
- 1997-04-04 PT PT97915220T patent/PT954290E/pt unknown
- 1997-04-04 KR KR10-1998-0708056A patent/KR100439614B1/ko not_active Expired - Fee Related
- 1997-04-04 DE DE69722247T patent/DE69722247T2/de not_active Expired - Lifetime
- 1997-04-04 NZ NZ332576A patent/NZ332576A/xx not_active IP Right Cessation
- 1997-04-04 PL PL32928597A patent/PL187764B1/pl unknown
- 1997-04-10 ZA ZA9703054A patent/ZA973054B/xx unknown
- 1997-04-10 MY MYPI97001576A patent/MY115535A/en unknown
-
1998
- 1998-10-08 NO NO19984703A patent/NO321862B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PL329285A1 (en) | 1999-03-15 |
| WO1997037639A1 (fr) | 1997-10-16 |
| DE69722247T2 (de) | 2004-04-01 |
| NO984703D0 (no) | 1998-10-08 |
| CZ294342B6 (cs) | 2004-12-15 |
| ES2200166T3 (es) | 2004-03-01 |
| BR9708772A (pt) | 2000-01-04 |
| NZ332576A (en) | 2000-03-27 |
| CZ325498A3 (cs) | 1999-03-17 |
| EP0954290B1 (fr) | 2003-05-21 |
| ZA973054B (en) | 1998-06-01 |
| DE69722247D1 (de) | 2003-06-26 |
| PL187764B1 (pl) | 2004-10-29 |
| KR100439614B1 (ko) | 2004-10-14 |
| AU711089B2 (en) | 1999-10-07 |
| JP2000507561A (ja) | 2000-06-20 |
| EP0954290A1 (fr) | 1999-11-10 |
| AU2283297A (en) | 1997-10-29 |
| CN1218396A (zh) | 1999-06-02 |
| TR199802034T2 (xx) | 1999-02-22 |
| NO321862B1 (no) | 2006-07-17 |
| CA2173818A1 (fr) | 1997-10-11 |
| MY115535A (en) | 2003-07-31 |
| ATE240719T1 (de) | 2003-06-15 |
| KR20000005337A (ko) | 2000-01-25 |
| PT954290E (pt) | 2003-10-31 |
| DK0954290T3 (da) | 2003-09-22 |
| NO984703L (no) | 1998-12-08 |
| US5885615A (en) | 1999-03-23 |
| IL126477A0 (en) | 1999-08-17 |
| JP4166278B2 (ja) | 2008-10-15 |
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