WO1997009036A2 - Improved pharmaceutical ion exchange resin composition - Google Patents
Improved pharmaceutical ion exchange resin composition Download PDFInfo
- Publication number
- WO1997009036A2 WO1997009036A2 PCT/GB1996/002156 GB9602156W WO9709036A2 WO 1997009036 A2 WO1997009036 A2 WO 1997009036A2 GB 9602156 W GB9602156 W GB 9602156W WO 9709036 A2 WO9709036 A2 WO 9709036A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- sugar
- sugar alcohol
- process according
- ion exchange
- exchange resin
- Prior art date
Links
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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/58—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. poly[meth]acrylate, polyacrylamide, polystyrene, polyvinylpyrrolidone, polyvinylalcohol or polystyrene sulfonic acid resin
- A61K47/585—Ion exchange resins, e.g. polystyrene sulfonic acid resin
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1617—Organic compounds, e.g. phospholipids, fats
- A61K9/1623—Sugars or sugar alcohols, e.g. lactose; Derivatives thereof; Homeopathic globules
Definitions
- the present invention relates to a process of preparing pharmaceutical ion exchange resin compositions
- European Patent Application Publication No 368682 describes a process for the preparation of a pharmaceutical ion exchange resin composition that is readily dispersible in water comprising granulating an ion exchange resin having a pharmacologically active ingredient bound thereto with a sugar or a sugar alcohol in the presence of sufficient water to facilitate granulation
- Unit doses are prepared by filling e g capsules, sachets or other suitable containers with the granules
- the product of EP 368682 is satisfactory when made at pilot scale of manufacture (ca 10-12 kg), it has been found at production scale of manufacture (ca 100kg or more), that a variable level of pharmaceutically active ingredient is obtained in unit doses prepared from a single batch of granulate
- unit doses prepared from one batch of granulate and with a desired morphine content of 20mg may have morphine contents in the range of 18 5 to 23 5 mg and a mean content of 21 5 mg (coefficient of variations 8 3
- One aim of the present invention is to provide a process for preparing a pharmaceutical ion exchange resin composition which can be used to prepare unit doses having a reduced inter- unit dose variability of the content of active ingredient This has, surprisingly, been achieved by using an aqueous solution of a sugar or sugar alcohol as a granulating medium instead of water
- a process for preparing a granular pharmaceutical ion exchange resin composition that is readily dispersible in water by granulating an ion exchange resin, having a pharmacologically active ingredient bound thereto, with a particulate sugar or sugar alcohol, characterised by the use of an aqueous solution of a sugar or sugar alcohol as a granulating medium
- compositions prepared by the process of this invention disperse readily in water
- dispersion readily occurs inside a minute upon stirring in sufficient water
- a composition of this invention disperses with stirring with 60 seconds in at least 5. for instance 20 times its own weight in water
- the aqueous solution of sugar or sugar alcohol is conveniently added to a mixture of resin and particulate sugar or sugar alcohol during granulation.
- the sugar or sugar alcohol in the granulating fluid is identical to the sugar or sugar alcohol with which the resin is granulated.
- the sugar or the sugar alcohol present in the solution and present as solid has a molecular weight of from 90 to 550, especially from 150 to 370.
- the preferred sugars are mono- or di-saccharides and the preferred sugar alcohols are reduced mono- or di ⁇ saccharides.
- Suitable sugars/sugar alcohols are sucrose, dextrose, maltose, fructose, lactose, mannitol, sorbitol or, which is preferred, xylitol.
- the particulate sugar/sugar alcohol granules is preferably finely divided, preferably having particle sizes of 600 microns or less. In a particularly preferred embodiment of the present process, at least 90% (by weight) of the particulate sugar/sugar alcohol granules will have particle sizes of 250 microns or less.
- the sugar or sugar alcohol is present in the solution at a concentration of 40% w/w to 60%) w/w, e.g. 45%o w/w to 55% w/w most preferably about 50% w/w
- the amount of granulating medium employed is from 1 to 20%, especially from 4 to 15%), by weight of the weight of the final dry weight of the complex/sugar, sugar alcohol mix.
- the granules formed are then dried, preferably, until their water content is below 0.35%> (by weight) (when measured by the Karl Fischer method of moisture analysis).
- Any acidic or basic drug may be bound to the ion exchange resin.
- active ingredients having a biological half life of 8 hours or less are used.
- Suitable ingredients include
- Narcotic analgesics such as codeine, dihydrocodeine, hydromorphone, morphine, pentazocine and propoxyphene,
- Syrnpathomimetics such as norephedrine and pseudoephedrine
- Antitussives such as dextromethorphan
- Analgesics such as aspirin and tramadol
- Anticholinergics such as atropine, lpratropium bromide and scopolamine
- vu Muscle relaxants such as cyclobenzap ⁇ ne and papave ⁇ ne
- vm Bronchodilators such as salbutamol, terbutalme and theophylline
- Antibiotics such as amoxycillin, ampicillin, azlocil n, bacampicil n, cefamandole, cefomcid, cefotaxime, cefotetan, cefoxitin, ceft ⁇ axone, mezlocillin and piperacilhn,
- Antidepressants such as bupropion, nomifensine and nort ⁇ ptyhne
- xi Antiasthmatics such as cromolyn
- xii Antineoplastics such as tamoxifen
- xi ⁇ Antiepileptics such as valproic acid and phenvtoin
- Cardiovascular agents such as propranolol
- ion exchange resins have acrylic, methacrylic, phenol-formaldehyde or dextran matrices
- a preferred cationic ion exchange resin is a gel styrene-divinyl benzene sulphonic acid resin, such as Amberlite IR P69 (Trade Mark) and Dowex 50W-8 100-200 (Trade Mark)
- the particle size and the degree of cross linking of the resin is determined by amongst other factors, the drug employed and the rate of drug release required
- the resin has a particle size of from 0 045 to 1mm, especially from 0 045 to 0 5mm
- the preferred degree of cross-linking is from 2% to 16%, especially from 8%> to 12%
- the amount of drug bound to the resin is also determined by the choice of drug, as well as by the resin employed.
- the weight ratio of bound drug to resin is from 1 :3 to 2: 1, especially from 2:3 to 3:2.
- Adsorption of the drug onto the ion exchange resin particles is a well known technique as shown in GB 824337, GB 1218102 and US 2990332 and demonstrated in the examples of EP-A 368682.
- the drug is mixed with an aqueous suspension of the resin and the complex is then dried. Adsorption of the drug onto the resin is detected by an assay of the suspending fluid.
- the process of the present invention provides drug resin complexes or granules which upon oral administration result in adsorption of the active ingredient from the gastro-intestinal tract enabling therapeutically effective blood levels of the active ingredient to be achieved: suitably the compositions are controlled release compositions and in their most preferred form enable therapeutically effective blood levels to be maintained upon dosing in at least 12 hourly intervals.
- the drug-resin complex or the granules may be film coated with a material that permits release ofthe drug from the composition at a controlled rate.
- the film coat will generally include a water insoluble material such as
- the film coat comprises a mixture of the water insoluble material and a water soluble material.
- the ratio of water insoluble to water soluble material is determined by, amongst other factors, the release rate required and the solubility characteristics of the materials selected.
- the water soluble material may be, for example, triacetin, propylene glycol, polyethylene glycol, polyvinylpyrrolidone or, which is preferred, a water soluble cellulose, such as hydroxypropyl cellulose, or especially, hydroxypropylmethyl cellulose
- Suitable combinations of water insoluble and water soluble materials for the film coat include shellac and polyvinylpyrrolidone or, which is preferred, ethyl cellulose and hydroxypropylmethyl cellulose
- composition may then be presented in a suitable dosage form, such as a capsule or a sachet This is done simply by filling the capsule/sachet with the finished composition
- a morphine sulphate controlled release resin was prepared as described in Example 1 of EP- A 368682
- Comparative Example 1 The process of Comparative Example 1 was repeated three times except that the amount of milled xylitol added to the mixer granulator was 52.98 kg and 8kg of a 50% w/w solution of xylitol was gradually added to the blend of morphine resin complex and milled xylitol over 18 minutes.
- Example 1 The process of Example 1 was repeated four times using the relative amounts of ingredients given below to provide Batches 10 to 13 respectively which were then used to prepare sachets having nominal strengths of mo ⁇ hine in the range of 30 mg (Batch 10), 60 mg (Batch 1 1) 100 mg (Batch 12) and 200 mg (Batch 13). mg Mo ⁇ hine sulphate/Dowex W50 x 8 100-200 (Trade Mark) resin complex 63.0 Xylitol USNF milled 458.0
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP96928628A EP0847273B1 (en) | 1995-09-01 | 1996-09-02 | Improved pharmaceutical ion exchange resin composition |
AT96928628T ATE213152T1 (en) | 1995-09-01 | 1996-09-02 | IMPROVED DRUGS USING AN ION EXCHANGE RESIN |
US09/029,151 US6077532A (en) | 1995-09-01 | 1996-09-02 | Pharmaceutical ion exchange resin composition |
AU68347/96A AU6834796A (en) | 1995-09-01 | 1996-09-02 | Improved pharmaceutical ion exchange resin composition |
DE69619250T DE69619250T2 (en) | 1995-09-01 | 1996-09-02 | IMPROVED MEDICINES WITH AN ION EXCHANGE RESIN |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9517883.6 | 1995-09-01 | ||
GBGB9517883.6A GB9517883D0 (en) | 1995-09-01 | 1995-09-01 | Improved pharmaceutical ion exchange resin composition |
Publications (2)
Publication Number | Publication Date |
---|---|
WO1997009036A2 true WO1997009036A2 (en) | 1997-03-13 |
WO1997009036A3 WO1997009036A3 (en) | 1997-04-24 |
Family
ID=10780065
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB1996/002156 WO1997009036A2 (en) | 1995-09-01 | 1996-09-02 | Improved pharmaceutical ion exchange resin composition |
Country Status (9)
Country | Link |
---|---|
US (1) | US6077532A (en) |
EP (1) | EP0847273B1 (en) |
AT (1) | ATE213152T1 (en) |
AU (1) | AU6834796A (en) |
DE (1) | DE69619250T2 (en) |
ES (1) | ES2170258T3 (en) |
GB (1) | GB9517883D0 (en) |
PT (1) | PT847273E (en) |
WO (1) | WO1997009036A2 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1998050018A1 (en) * | 1997-05-06 | 1998-11-12 | Xiao Yu Wu | Drug delivery system |
WO2001062236A2 (en) * | 2000-02-24 | 2001-08-30 | Pharmacia & Upjohn Company | New drug combinations comprising a norepinephrine reuptake inhibitor and an antimuscarinic agent |
EP1834634A2 (en) * | 2006-03-08 | 2007-09-19 | Rentschler Pharma GmbH | Pharmaceutical multiple-unit composition |
Families Citing this family (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999032119A1 (en) * | 1997-12-22 | 1999-07-01 | Euro-Celtique, S.A. | Opioid agonist/antagonist combinations |
UA53774C2 (en) * | 1997-12-22 | 2003-02-17 | Еро-Селтік, С.А. | Method of reducing abuse potential of an oral dosage form of opioid analgesic |
US6221308B1 (en) * | 1999-04-20 | 2001-04-24 | Corning Incorporated | Method of making fired bodies |
HU229705B1 (en) * | 2000-02-08 | 2014-05-28 | Euro Celtique Sa | Tamper-resistant oral opioid agonist formulations |
ATE493130T1 (en) | 2001-05-11 | 2011-01-15 | Endo Pharmaceuticals Inc | MEDICINAL FORM CONTAINING OPIOID AGAINST ABUSE |
DE60230632D1 (en) * | 2001-07-18 | 2009-02-12 | Euro Celtique Sa | PHARMACEUTICAL COMBINATIONS OF OXYCODONE AND NALOXONE |
WO2003013433A2 (en) | 2001-08-06 | 2003-02-20 | Euro-Celtique S.A. | Sequestered antagonist formulations |
ATE431738T1 (en) | 2001-08-06 | 2009-06-15 | Euro Celtique Sa | OPIOID AGONIST FORMULATIONS WITH RELEASABLE AND SEQUESTRED ANTAGONIST |
US20030044458A1 (en) | 2001-08-06 | 2003-03-06 | Curtis Wright | Oral dosage form comprising a therapeutic agent and an adverse-effect agent |
US8128957B1 (en) | 2002-02-21 | 2012-03-06 | Valeant International (Barbados) Srl | Modified release compositions of at least one form of tramadol |
US20040067216A1 (en) * | 2002-02-22 | 2004-04-08 | Karki Shyam B. | Hiv protease inhibitors supported on cation exchange resins for oral administration |
EP2243471A1 (en) | 2002-04-05 | 2010-10-27 | Euro-Celtique S.A. | Matrix for sustained, invariant and independent release of active compounds |
DK1551372T3 (en) | 2002-09-20 | 2018-07-23 | Alpharma Pharmaceuticals Llc | SEQUERATION SUBSTANCES AND RELATED COMPOSITIONS AND PROCEDURES |
US20040202717A1 (en) | 2003-04-08 | 2004-10-14 | Mehta Atul M. | Abuse-resistant oral dosage forms and method of use thereof |
TWI347201B (en) | 2003-04-21 | 2011-08-21 | Euro Celtique Sa | Pharmaceutical products,uses thereof and methods for preparing the same |
AU2004270188B8 (en) * | 2003-09-03 | 2010-04-29 | Mallinckrodt Inc. | Granular sustained release preparation and production thereof |
US20050181050A1 (en) * | 2004-01-28 | 2005-08-18 | Collegium Pharmaceutical, Inc. | Dosage forms using drug-loaded ion exchange resins |
US20070232695A1 (en) * | 2004-01-28 | 2007-10-04 | Collegium Pharmaceutical, Inc. | Gelled Periodontal Anesthetic Preparation |
EP1604666A1 (en) * | 2004-06-08 | 2005-12-14 | Euro-Celtique S.A. | Opioids for the treatment of the Chronic Obstructive Pulmonary Disease (COPD) |
WO2006081518A2 (en) * | 2005-01-28 | 2006-08-03 | Collegium Pharmaceutical, Inc. | Non-ionic non-aqueous vehicles for topical and oral administration of carrier-complexed active agents |
EP1702558A1 (en) * | 2005-02-28 | 2006-09-20 | Euro-Celtique S.A. | Method and device for the assessment of bowel function |
US8343546B2 (en) * | 2005-09-13 | 2013-01-01 | Coating Place, Inc. | Ion exchange resin treated to control swelling |
CN101677963B (en) | 2006-06-19 | 2012-05-30 | 奥尔制药公司 | Pharmaceutical compositions |
EP2120945A1 (en) * | 2007-02-28 | 2009-11-25 | Collegium Pharmaceutical, Inc. | Antihistamine combination |
US8623418B2 (en) | 2007-12-17 | 2014-01-07 | Alpharma Pharmaceuticals Llc | Pharmaceutical composition |
DK2405915T3 (en) | 2009-03-10 | 2019-02-11 | Euro Celtique Sa | PHARMACEUTICAL COMPOSITIONS WITH IMMEDIATE RELEASE INCLUDING OXYCODON AND NALOXON |
KR20180037074A (en) | 2013-07-23 | 2018-04-10 | 유로-셀티큐 에스.에이. | A combination of oxycodone and naloxone for use in treating pain in patients suffering from pain and a disease resulting in intestinal dysbiosis and/or increasing the risk for intestinal bacterial translocation |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0200252A1 (en) * | 1985-05-02 | 1986-12-10 | Yamanouchi Europe B.V. | Tablets comprising trimethoprim and a sulfonamide |
EP0329977A2 (en) * | 1988-02-25 | 1989-08-30 | Xyrofin Oy | A xylitol-based binding and diluting agent and a process for the production thereof |
EP0368682A1 (en) * | 1988-11-11 | 1990-05-16 | Euroceltique S.A. | Pharmaceutical ion exchange resin composition |
WO1992016209A1 (en) * | 1991-03-14 | 1992-10-01 | Reanal Finomvegyszergyár | Granules and veterinary compositions comprising a water-soluble complex of flumequine |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3627583A (en) * | 1969-04-29 | 1971-12-14 | Sucrest Corp | Direct compression vehicles |
EP0328877A1 (en) * | 1988-02-18 | 1989-08-23 | Oerlikon-Contraves AG | Projectile with a fragmenting shell |
-
1995
- 1995-09-01 GB GBGB9517883.6A patent/GB9517883D0/en active Pending
-
1996
- 1996-09-02 DE DE69619250T patent/DE69619250T2/en not_active Expired - Lifetime
- 1996-09-02 ES ES96928628T patent/ES2170258T3/en not_active Expired - Lifetime
- 1996-09-02 EP EP96928628A patent/EP0847273B1/en not_active Expired - Lifetime
- 1996-09-02 AU AU68347/96A patent/AU6834796A/en not_active Abandoned
- 1996-09-02 AT AT96928628T patent/ATE213152T1/en active
- 1996-09-02 WO PCT/GB1996/002156 patent/WO1997009036A2/en active IP Right Grant
- 1996-09-02 US US09/029,151 patent/US6077532A/en not_active Expired - Lifetime
- 1996-09-02 PT PT96928628T patent/PT847273E/en unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0200252A1 (en) * | 1985-05-02 | 1986-12-10 | Yamanouchi Europe B.V. | Tablets comprising trimethoprim and a sulfonamide |
EP0329977A2 (en) * | 1988-02-25 | 1989-08-30 | Xyrofin Oy | A xylitol-based binding and diluting agent and a process for the production thereof |
EP0368682A1 (en) * | 1988-11-11 | 1990-05-16 | Euroceltique S.A. | Pharmaceutical ion exchange resin composition |
WO1992016209A1 (en) * | 1991-03-14 | 1992-10-01 | Reanal Finomvegyszergyár | Granules and veterinary compositions comprising a water-soluble complex of flumequine |
Non-Patent Citations (1)
Title |
---|
P.H. LIST ET AL.: "hagers handbuch der pharmazeutischen praxis 4th edition volume 7 part A" 1971 , SPRINGER VERLAG , BERLIN, HEIDELBERG, NEW YORK XP002026431 see page 712 * |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1998050018A1 (en) * | 1997-05-06 | 1998-11-12 | Xiao Yu Wu | Drug delivery system |
WO2001062236A2 (en) * | 2000-02-24 | 2001-08-30 | Pharmacia & Upjohn Company | New drug combinations comprising a norepinephrine reuptake inhibitor and an antimuscarinic agent |
WO2001062236A3 (en) * | 2000-02-24 | 2002-03-07 | Upjohn Co | New drug combinations comprising a norepinephrine reuptake inhibitor and an antimuscarinic agent |
EP1834634A2 (en) * | 2006-03-08 | 2007-09-19 | Rentschler Pharma GmbH | Pharmaceutical multiple-unit composition |
EP1834634A3 (en) * | 2006-03-08 | 2007-10-03 | Rentschler Pharma GmbH | Pharmaceutical multiple-unit composition |
Also Published As
Publication number | Publication date |
---|---|
GB9517883D0 (en) | 1995-11-01 |
ES2170258T3 (en) | 2002-08-01 |
EP0847273B1 (en) | 2002-02-13 |
US6077532A (en) | 2000-06-20 |
ATE213152T1 (en) | 2002-02-15 |
AU6834796A (en) | 1997-03-27 |
DE69619250D1 (en) | 2002-03-21 |
WO1997009036A3 (en) | 1997-04-24 |
EP0847273A2 (en) | 1998-06-17 |
PT847273E (en) | 2002-06-28 |
DE69619250T2 (en) | 2002-08-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US6077532A (en) | Pharmaceutical ion exchange resin composition | |
EP0368682B1 (en) | Pharmaceutical ion exchange resin composition | |
JP5479086B2 (en) | Controlled release formulation containing drug-ion exchange resin complex | |
EP0367746B1 (en) | Sustained release drug-resin complexes | |
AU596804B2 (en) | A granular delayed-release form of pharmaceutically active substances | |
JP4077886B2 (en) | Long-acting heterodisperse hydrogel system of insoluble drugs | |
US5622722A (en) | Spheroid formulation | |
IL147212A (en) | Process for the manufacture of coated granules with masked taste | |
EP1536774A1 (en) | Taste masked dosage forms and processes for their preparation | |
KR100240362B1 (en) | Colestipol hydrochloride high-content tablets | |
JP2000178182A (en) | Disintegrable composition | |
WO2008157228A1 (en) | New methods for taste-masking | |
AU643263B2 (en) | Composition | |
JPH069376A (en) | Coated core pharmaceutical preparation | |
EP0557064B1 (en) | Modified release formulation | |
IE990009A1 (en) | Taste-masked composition | |
WO2009130715A1 (en) | Rapidly disintegrating oral compositions of tramadol | |
JPH09157158A (en) | Preparation compounded with galenical |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A2 Designated state(s): AL AM AT AU AZ BB BG BR BY CA CH CN CU CZ DE DK EE ES FI GB GE HU IL IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK TJ TM TR TT UA UG US UZ VN AM AZ BY KG KZ MD RU TJ TM |
|
AL | Designated countries for regional patents |
Kind code of ref document: A2 Designated state(s): KE LS MW SD SZ UG AT BE CH DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI |
|
AK | Designated states |
Kind code of ref document: A3 Designated state(s): AL AM AT AU AZ BB BG BR BY CA CH CN CU CZ DE DK EE ES FI GB GE HU IL IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK TJ TM TR TT UA UG US UZ VN AM AZ BY KG KZ MD RU TJ TM |
|
AL | Designated countries for regional patents |
Kind code of ref document: A3 Designated state(s): KE LS MW SD SZ UG AT BE CH DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI |
|
DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 1996928628 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 09029151 Country of ref document: US |
|
WWP | Wipo information: published in national office |
Ref document number: 1996928628 Country of ref document: EP |
|
REG | Reference to national code |
Ref country code: DE Ref legal event code: 8642 |
|
NENP | Non-entry into the national phase |
Ref country code: CA |
|
WWG | Wipo information: grant in national office |
Ref document number: 1996928628 Country of ref document: EP |