CA1276560C - Process for producing a sustained release ibuprofen preparation - Google Patents
Process for producing a sustained release ibuprofen preparationInfo
- Publication number
- CA1276560C CA1276560C CA000525825A CA525825A CA1276560C CA 1276560 C CA1276560 C CA 1276560C CA 000525825 A CA000525825 A CA 000525825A CA 525825 A CA525825 A CA 525825A CA 1276560 C CA1276560 C CA 1276560C
- Authority
- CA
- Canada
- Prior art keywords
- mixture
- ibuprofen
- microspheres
- tablets
- cellulose
- 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 - Fee Related
Links
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 title claims abstract description 43
- 229960001680 ibuprofen Drugs 0.000 title claims abstract description 28
- 238000000034 method Methods 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 9
- 238000013268 sustained release Methods 0.000 title claims description 4
- 239000012730 sustained-release form Substances 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims abstract description 21
- 239000004005 microsphere Substances 0.000 claims abstract description 17
- 239000001913 cellulose Substances 0.000 claims abstract description 14
- 235000010980 cellulose Nutrition 0.000 claims abstract description 14
- 229920002678 cellulose Polymers 0.000 claims abstract description 12
- 239000011230 binding agent Substances 0.000 claims abstract description 10
- 239000007884 disintegrant Substances 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 4
- 229920000178 Acrylic resin Polymers 0.000 claims abstract description 4
- 239000004922 lacquer Substances 0.000 claims abstract description 4
- 229920002472 Starch Polymers 0.000 claims description 5
- 239000008107 starch Substances 0.000 claims description 5
- 235000019698 starch Nutrition 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 239000012736 aqueous medium Substances 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 4
- 239000006185 dispersion Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- 239000008240 homogeneous mixture Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000001125 extrusion Methods 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000001814 pectin Substances 0.000 claims description 2
- 235000010987 pectin Nutrition 0.000 claims description 2
- 229920001277 pectin Polymers 0.000 claims description 2
- 238000007493 shaping process Methods 0.000 claims description 2
- 230000008961 swelling Effects 0.000 claims description 2
- 229920003134 Eudragit® polymer Polymers 0.000 claims 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- 125000005395 methacrylic acid group Chemical group 0.000 claims 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims 1
- 239000008108 microcrystalline cellulose Substances 0.000 claims 1
- 229940016286 microcrystalline cellulose Drugs 0.000 claims 1
- 230000003111 delayed effect Effects 0.000 abstract description 7
- 229940106135 cellulose Drugs 0.000 abstract description 2
- 239000003826 tablet Substances 0.000 description 27
- 239000000047 product Substances 0.000 description 17
- 239000002775 capsule Substances 0.000 description 11
- 238000013270 controlled release Methods 0.000 description 8
- -1 acryl Chemical group 0.000 description 4
- 230000036765 blood level Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 230000036470 plasma concentration Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 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 description 1
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 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
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 208000012659 Joint disease Diseases 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229940035564 duration Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000010248 fenbid Substances 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 229940071826 hydroxyethyl cellulose Drugs 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 125000005641 methacryl group Chemical group 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
- 229960002900 methylcellulose Drugs 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
- 229940071117 starch glycolate Drugs 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- 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
- 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)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Control Of El Displays (AREA)
- Manufacturing Of Tubular Articles Or Embedded Moulded Articles (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH2553/86A CH669523A5 (en, 2012) | 1986-06-25 | 1986-06-25 | |
| CH2553/86 | 1986-06-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1276560C true CA1276560C (en) | 1990-11-20 |
Family
ID=4236387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000525825A Expired - Fee Related CA1276560C (en) | 1986-06-25 | 1986-12-19 | Process for producing a sustained release ibuprofen preparation |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4867987A (en, 2012) |
| EP (1) | EP0250648B1 (en, 2012) |
| JP (1) | JPS635020A (en, 2012) |
| KR (1) | KR930008956B1 (en, 2012) |
| CN (1) | CN1023191C (en, 2012) |
| AT (1) | ATE66370T1 (en, 2012) |
| AU (1) | AU590370B2 (en, 2012) |
| CA (1) | CA1276560C (en, 2012) |
| CH (1) | CH669523A5 (en, 2012) |
| DE (1) | DE3681031D1 (en, 2012) |
| DK (1) | DK616186A (en, 2012) |
| ES (1) | ES2029228T3 (en, 2012) |
| FI (1) | FI88580C (en, 2012) |
| GR (1) | GR3002579T3 (en, 2012) |
| IL (1) | IL81045A (en, 2012) |
| NO (1) | NO173081C (en, 2012) |
| NZ (1) | NZ218734A (en, 2012) |
| ZA (1) | ZA869586B (en, 2012) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8705083D0 (en) * | 1987-03-04 | 1987-04-08 | Euro Celtique Sa | Spheroids |
| US4970081A (en) * | 1989-01-03 | 1990-11-13 | Sterling Drug Inc. | Controlled-release, low-dose aspirin formulation and method of treating vascular occlusive disease therewith |
| US5213807A (en) * | 1990-05-03 | 1993-05-25 | Chemburkar Pramod B | Pharmaceutical composition containing ibuprofen and a prostaglandin |
| JPH04230625A (ja) * | 1990-12-27 | 1992-08-19 | Standard Chem & Pharmaceut Corp Ltd | 噴霧乾燥したジクロフェナクナトリウムを含み腸溶性の被覆を有するマイクロカプセルからなる微分散した錠剤組成物の製造方法 |
| US5605930A (en) * | 1991-10-21 | 1997-02-25 | The United States Of America As Represented By The Department Of Health And Human Services | Compositions and methods for treating and preventing pathologies including cancer |
| US5773031A (en) * | 1996-02-27 | 1998-06-30 | L. Perrigo Company | Acetaminophen sustained-release formulation |
| US5637625A (en) * | 1996-03-19 | 1997-06-10 | Research Triangle Pharmaceuticals Ltd. | Propofol microdroplet formulations |
| FR2766089B1 (fr) * | 1997-07-21 | 2000-06-02 | Prographarm Lab | Comprime multiparticulaire perfectionne a delitement rapide |
| AU2002217647A1 (en) * | 2000-11-28 | 2002-06-11 | Irina Alekseevna Komissarova | Pharmaceutical composition, the use thereof and method for producing said composition |
| WO2004026283A1 (en) | 2002-09-20 | 2004-04-01 | Alpharma, Inc. | Sequestering subunit and related compositions and metohds |
| CN101115409B (zh) * | 2005-02-04 | 2013-03-27 | 菲利普莫里斯生产公司 | 具有纤维质滋味添加剂的香烟及过滤嘴 |
| DE102005037630A1 (de) | 2005-08-09 | 2007-02-15 | Glatt Gmbh | Verfahren zur Herstellung von Teilchen aus pharmazeutischen Substanzen, Teilchen aus pharmazeutischen Substanzen sowie deren Verwendung |
| CA2633266C (en) * | 2005-12-16 | 2011-08-02 | Hanmi Pharm. Co., Ltd. | Solid dispersion comprising an active ingredient having a low melting point and tablet for oral administration comprising same |
| SI2484346T1 (sl) | 2006-06-19 | 2017-05-31 | Alpharma Pharmaceuticals Llc | Farmacevtski sestavki |
| CA2665726C (en) * | 2006-10-11 | 2016-04-19 | Alpharma, Inc. | Pharmaceutical compositions |
| US8623418B2 (en) | 2007-12-17 | 2014-01-07 | Alpharma Pharmaceuticals Llc | Pharmaceutical composition |
| WO2009079521A1 (en) * | 2007-12-17 | 2009-06-25 | Alpharma Pharmaceuticals, Llc | Pharmaceutical composition |
| JP5953646B2 (ja) * | 2009-11-24 | 2016-07-20 | 大正製薬株式会社 | イブプロフェン含有固形製剤 |
| JP5819329B2 (ja) * | 2010-03-09 | 2015-11-24 | アルカーメス ファーマ アイルランド リミテッド | アルコール耐性腸溶性医薬組成物 |
| CA2936741C (en) | 2014-10-31 | 2018-11-06 | Purdue Pharma | Methods and compositions particularly for treatment of attention deficit disorder |
| US10722473B2 (en) | 2018-11-19 | 2020-07-28 | Purdue Pharma L.P. | Methods and compositions particularly for treatment of attention deficit disorder |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1228757B (de) * | 1962-06-28 | 1966-11-17 | Haessle Ab | Verfahren zur Herstellung eines in Wasser und Magensaft rasch zerfallenden UEberzuges auf festen Arzneiformen |
| JPS51127041A (en) * | 1975-04-23 | 1976-11-05 | Toyama Chem Co Ltd | A process for preparing novel 2-( substituted phenyl) alkane acids and their salts. |
| US4447454A (en) * | 1977-04-01 | 1984-05-08 | The Upjohn Company | Analgetic compounds, compositions and process of treatment |
| CA1125698A (en) * | 1978-03-09 | 1982-06-15 | Masaru Yoshida | Process for preparing a polymer composition |
| JPS6028809B2 (ja) * | 1979-08-21 | 1985-07-06 | 日本原子力研究所 | イブプロフエン徐放剤組成物の製造方法 |
| EP0052075A1 (de) * | 1980-11-12 | 1982-05-19 | Ciba-Geigy Ag | Körnige Arzneimittel-Retardform |
| IT1144911B (it) * | 1981-03-19 | 1986-10-29 | Pharmatec Spa | Composizione farmaceutica a rilascio controllato contenente ibuprofen |
| US4713249A (en) * | 1981-11-12 | 1987-12-15 | Schroeder Ulf | Crystallized carbohydrate matrix for biologically active substances, a process of preparing said matrix, and the use thereof |
| DK150008C (da) * | 1981-11-20 | 1987-05-25 | Benzon As Alfred | Fremgangsmaade til fremstilling af et farmaceutisk oralt polydepotpraeparat |
| DE3205504C2 (de) * | 1982-02-16 | 1983-12-01 | Dolorgiet Gmbh & Co Kg, 5300 Bonn | Äußerlich anwendbares, Ibuprofen enthaltendes Arzneimittel |
| US4587249A (en) * | 1982-07-22 | 1986-05-06 | Analgesic Associates | Analgesic and anti-inflammatory compositions comprising caffeine and methods of using same |
| US4486436A (en) * | 1982-07-22 | 1984-12-04 | Analgesic Associates | Analgesic and anti-inflammatory compositions comprising caffeine and methods of using same |
| NL191432C (nl) * | 1982-07-22 | 1995-07-04 | Vicks Richardson | Farmaceutisch preparaat omvattende naproxen en een andere werkzame verbinding. |
| GB2132887A (en) * | 1982-11-15 | 1984-07-18 | Procter & Gamble | Enteric-coated anti-inflammatory compositions |
| JPS59122425A (ja) * | 1982-12-27 | 1984-07-14 | Kaken Pharmaceut Co Ltd | 持続性製剤およびその製造法 |
| US4567183A (en) * | 1983-03-11 | 1986-01-28 | Analgesic Associates | Analgesic and anti-inflammatory compositions comprising xanthines and methods of using same |
| US4684516A (en) * | 1983-08-01 | 1987-08-04 | Alra Laboratories, Inc. | Sustained release tablets and method of making same |
| US4558051A (en) * | 1983-10-11 | 1985-12-10 | Richardson-Vicks, Inc. | Analgesic and anti-inflammatory compositions comprising xanthines and methods of using same |
| US4522826A (en) * | 1984-02-08 | 1985-06-11 | Richardson-Vicks Inc. | Analgesic and anti-inflammatory compositions comprising diphenhydramine and methods of using same |
| US4585783A (en) * | 1984-02-08 | 1986-04-29 | Richardson-Vicks, Inc. | Analgesic and anti-inflammatory compositions comprising diphenhydramine and methods of using same |
| DK62184D0 (da) * | 1984-02-10 | 1984-02-10 | Benzon As Alfred | Diffusionsovertrukket polydepotpraeparat |
| US4609675A (en) * | 1984-08-17 | 1986-09-02 | The Upjohn Company | Stable, high dose, high bulk density ibuprofen granulations for tablet and capsule manufacturing |
| IE58110B1 (en) * | 1984-10-30 | 1993-07-14 | Elan Corp Plc | Controlled release powder and process for its preparation |
| US4666705A (en) * | 1985-06-03 | 1987-05-19 | E. R. Squibb & Sons, Inc. | Controlled release formulation |
| GB8519310D0 (en) * | 1985-07-31 | 1985-09-04 | Zyma Sa | Granular active substances |
-
1986
- 1986-06-25 CH CH2553/86A patent/CH669523A5/de not_active IP Right Cessation
- 1986-12-16 AT AT86117458T patent/ATE66370T1/de not_active IP Right Cessation
- 1986-12-16 EP EP86117458A patent/EP0250648B1/de not_active Expired - Lifetime
- 1986-12-16 ES ES198686117458T patent/ES2029228T3/es not_active Expired - Lifetime
- 1986-12-16 DE DE8686117458T patent/DE3681031D1/de not_active Expired - Lifetime
- 1986-12-19 CN CN86108644A patent/CN1023191C/zh not_active Expired - Fee Related
- 1986-12-19 FI FI865227A patent/FI88580C/fi not_active IP Right Cessation
- 1986-12-19 DK DK616186A patent/DK616186A/da not_active Application Discontinuation
- 1986-12-19 KR KR1019860010971A patent/KR930008956B1/ko not_active Expired - Fee Related
- 1986-12-19 NO NO865195A patent/NO173081C/no unknown
- 1986-12-19 US US06/944,552 patent/US4867987A/en not_active Expired - Fee Related
- 1986-12-19 AU AU66807/86A patent/AU590370B2/en not_active Ceased
- 1986-12-19 NZ NZ218734A patent/NZ218734A/xx unknown
- 1986-12-19 JP JP61303589A patent/JPS635020A/ja active Pending
- 1986-12-19 IL IL81045A patent/IL81045A/xx not_active IP Right Cessation
- 1986-12-19 ZA ZA869586A patent/ZA869586B/xx unknown
- 1986-12-19 CA CA000525825A patent/CA1276560C/en not_active Expired - Fee Related
-
1991
- 1991-08-22 GR GR91401076T patent/GR3002579T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK616186D0 (da) | 1986-12-19 |
| GR3002579T3 (en) | 1993-01-25 |
| DK616186A (da) | 1987-12-26 |
| DE3681031D1 (de) | 1991-09-26 |
| ATE66370T1 (de) | 1991-09-15 |
| CN86108644A (zh) | 1988-01-06 |
| ZA869586B (en) | 1988-07-27 |
| EP0250648A3 (en) | 1988-03-23 |
| US4867987A (en) | 1989-09-19 |
| NO173081C (no) | 1993-10-27 |
| FI88580B (fi) | 1993-02-26 |
| KR880000090A (ko) | 1988-03-23 |
| KR930008956B1 (ko) | 1993-09-17 |
| EP0250648B1 (de) | 1991-08-21 |
| NO173081B (no) | 1993-07-19 |
| CH669523A5 (en, 2012) | 1989-03-31 |
| NO865195D0 (no) | 1986-12-19 |
| FI88580C (fi) | 1993-06-10 |
| EP0250648A2 (de) | 1988-01-07 |
| NZ218734A (en) | 1990-03-27 |
| AU6680786A (en) | 1988-01-07 |
| FI865227A7 (fi) | 1987-12-26 |
| FI865227A0 (fi) | 1986-12-19 |
| IL81045A0 (en) | 1987-03-31 |
| NO865195L (no) | 1987-12-28 |
| AU590370B2 (en) | 1989-11-02 |
| IL81045A (en) | 1990-11-05 |
| ES2029228T3 (es) | 1992-08-01 |
| JPS635020A (ja) | 1988-01-11 |
| CN1023191C (zh) | 1993-12-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |