WO1995025516A1 - Pharmaceutical formulations containing beta-lactam antibiotics and an alkyl sulphate surfactant - Google Patents
Pharmaceutical formulations containing beta-lactam antibiotics and an alkyl sulphate surfactant Download PDFInfo
- Publication number
- WO1995025516A1 WO1995025516A1 PCT/EP1995/001039 EP9501039W WO9525516A1 WO 1995025516 A1 WO1995025516 A1 WO 1995025516A1 EP 9501039 W EP9501039 W EP 9501039W WO 9525516 A1 WO9525516 A1 WO 9525516A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- beta
- granule
- pharmaceutical
- granules
- group
- 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
- A61K9/1617—Organic compounds, e.g. phospholipids, fats
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5005—Wall or coating material
- A61K9/5021—Organic macromolecular compounds
- A61K9/5026—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
Definitions
- This invention relates to pharmaceutical formulations, in particular to beta-lactam antibiotic formulations in the form of substantially spherical granules.
- the active ingredient comprises a beta-lactam antibiotic and/or beta-lactamase inhibitor
- it is frequently necessary to provide the formulation in the form of granules for example for making up into tablets, capsules or sachet formulations etc.
- it is desirable that the granules are substantially spherical.
- substantially spherical as used herein is intended to include spherical, ellipsoidal, e.g. of eccentricity up to no more than 2, preferably up to no more than 1.5, oblate spheroidal, e.g. having its longest axes up to no more than 2 times, preferably up to no more than 1.5 times longer than its shortest axis, polyhedral with at least 12 faces having predominantly curved rather than angular edges, and substantially equiaxial.
- the term also includes the shape of what are known in the art as "maru s".
- the terms "spheronised” and “spheronisation” are terms of the art.
- substantially spherical granules when granules of relatively water soluble antibiotics, and of beta-lactamase inhibitors such as salts of clavulanic acid such as potassium clavulanate are to be coated, as the angles of angular granules can present weak points in the coat via which the antibiotic or inhibitor may be leached out. Problems have been encountered in providing such antibiotics and beta-lactamase inhibitors in the form of granules, particularly in the form of substantially spherical granules.
- a pharmaceutical granule comprising: an active ingredient which comprises one or more beta-lactam antibiotics and/or one or more beta-lactamase inhibitors; and one or more surfactants which are Group I or Group II metal (CJO-17) alkyl sulphates.
- the invention further provides a process for the preparation of a pharmaceutical granule, comprising admixing one or more beta-lactam antibiotics, and/or one or more beta-lactamase inhibitors with one or more surfactants which are Group I or Group ⁇ metal (C ⁇ o-17) alkyl sulphates, and then granulating the mixture.
- a pharmaceutical granule comprising admixing one or more beta-lactam antibiotics, and/or one or more beta-lactamase inhibitors with one or more surfactants which are Group I or Group ⁇ metal (C ⁇ o-17) alkyl sulphates, and then granulating the mixture.
- the granule is primarily intended for oral administration, and consequently preferred antibiotics are orally absorbed penicillins (which term includes penicillins penems, penams, carbapenems etc.) or cephalosporins.
- Preferred beta-lactam antibiotics are amoxyc ⁇ lin, for example as its trihydrate, and ampicillin.
- a preferred beta-lactamase inhibitor is a salt of clavulanic acid, especially group I metal salts thereof such as potassium clavulanate.
- a preferred combination of beta-lactamase inhibitor and antibiotic is potassium clavulanate : amoxycillin, as amoxycillin trihydrate or sodium amoxycillin, for example as crystalline anhydrous sodium amoxycillin as described in EP 0131147.
- a preferred ratio of clavulanate : amoxycillin is in the range 1 : 1 to 1 : 12 inclusive, particularly 1 : 2 to 1: 8, expressed in terms of weight ratios of the free acids.
- the Group I or Group ⁇ metal alkyl sulphate has a formula
- the surfactant(s) is preferably a sodium alkyl sulphate, for example sodium lauryl sulphate.
- the granule may also comprise conventional granulating aids such as polyvinylpyrrolidone such as KoUidon K12-30 (Trade Mark) or the proprietary hydroxymethyl cellulose material "Pha ⁇ nacoat 603" (Trade Mark), fillers / spheronising aids such as colloidal silica such as Aerosil 200 (Trade Mark) and/or cellulose derivatives such as microcrystalline cellulose, e.g. Avicel (Trade Mark).
- a salt of clavulanic acid e.g. potassium clavulanate either as the sole beta-lactamase inhibitor content or in admixture with other beta-lactamase inhibitors then it is preferred that the granule also contains an amino acid, suitably glycine.
- the relative proportions of the above components in the granule are suitably as follows.
- Antibiotic, beta-lactamase inhibitors or combination thereof 50 wt. % or more e.g. 80% or more.
- Surfactant 0.5 - 5 wt. % e.g. 0.5 - 1.5 wt. %.
- Granulating aid 0 - 7.5 wt. %, typically if the granule comprises or contains a salt of clavulanic acid as the sole or principal active ingredient content or in admixture with another antibiotic 3 - 7.5 wt. %, e.g. 4 ⁇ 1 wt. %.
- Fillers/spheronising aids 0 - 25 wt.
- % e.g. 0 - 10 wt. % . If an amino acid is present in the granule, for example together with a salt of clavulanic acid, then suitably 1 - 50 wt. %, e.g. 5 - 15 wt. %. may be present. These weight percentages are expressed as total granule weight.
- the shape of the granules is preferably substantially spherical, as defined above, with a size range between 10-44 mesh, e.g. 12-30 mesh.
- the invention further provides a process for the preparation of a pharmaceutical granule, comprising admixing one or more beta-lactam antibiotics, and/or one or more beta-lactamase inhibitors with one or more surfactants which are Group I or Group ⁇ metal (CJO- ⁇ ) alkyl sulphates, and then granulating the mixture.
- These granules may be prepared by a granulation process comprising for example mixing the milled ingredients with a suitable liquid, or by mixing the milled ingredients less the granulating aid with a solution or suspension of the granulating aid, followed by extrusion and preferably spheronisation, e.g. "marumerisation".
- the suitable liquid may be an organic liquid or water
- a suitable liquid may be an organic liquid such as an isopropyl alcohol: methylene dichloride mixture, typically in a 1:2-3 volume: volume ratio.
- Salts of clavulanic acid such as potassium clavulanate are extremely water sensitive, so it is important that such salts are handled in extremely dry conditions, suitably 30% RH or less. It has been found that spheronised granules, such as marums may conveniently be prepared using the above formulations and process.
- the granules of this invention are suited to coating, for example with water-resistant or enteric coatings. This is particularly so in the case of granules of the invention in which the active ingredient comprises or includes a salt of clavulanic acid.
- the invention also provides a granule as described above, coated with a coating, which may be an at least partly water-resistant, suitably an enteric, coating.
- the invention also provides a process wherein a granule as described above is coated with a coating, which may be an at least partly water-resistant, suitably an enteric, coating.
- a coating which may be an at least partly water-resistant, suitably an enteric, coating.
- An enteric coating may for example be an essentially conventional enteric coating material known for coating antibiotic granules.
- Suitable coating materials are pharmaceutically acceptable methacrylic acid copolymers such as those described in the USP/NF, and such polymers of types A, B and C as described therein may be suitable.
- Suitable generic classes and specific examples of pharmaceutically acceptable methacrylic acid copolymer are known polymers which are copolymers of acrylic and methacrylic esters with a low content of quaternary ammonium groups, for example having a molar ratio of such ammonium groups : remaining (meth)acrylic esters of 1 : _ ⁇ . 10, for example around 1 : 20 or 1 : 40, and with a mean molecular weight of around 150000.
- Such polymers correspond to USP/NF 2 "Ammonio methacrylate copolymers, Type A and Type B".
- methacrylic acid copolymer examples include polymers which are copolymers, anionic in character, based on methacrylic acid and methyl methacrylate, for example having a ratio of free carboxyl groups : methyl-esterified carboxyl groups of 1 : >3, e.g. around 1 : 1 or 1 : 2, and with a mean molecular weight of 135000.
- Such polymers are sold under the trade name Eudragit TM, such as the Eudragit L series e.g. Eudragit L 12.5 TM, Eudragit L 12.5P TM, Eudragit L100 TM, Eudragit L 100-55 TM, Eudragit L-30 TM, Eudragit L-30 D-55 TM, the Eudragit S TM series e.g. Eudragit S 12.5, Eudragit S 12.5P TM, Eudragit S100 TM, the Eudragit NETM series e.g Eudragit NE 30D TM, the Eudragit RL TM series, e.g.
- enteric polymers the term "enteric polymer” is a term of the art referring to a polymer which is preferentially soluble in the less acid environment of the intestine relative to the more acid environment of the stomach), for example having a solubility in aqueous media at pH 5.5 and above.
- enteric polymers the term "enteric polymer” is a term of the art referring to a polymer which is preferentially soluble in the less acid environment of the intestine relative to the more acid environment of the stomach, for example having a solubility in aqueous media at pH 5.5 and above.
- enteric polymers the term "enteric
- the coating may be applied using either an aqueous medium or a non- aqueous medium such as an organic liquid, for example a methanol: methylene dichloride mixture.
- a non-aqueous medium may be more suitable if the active ingredient comprises or contains a clavulanate salt.
- the choice of plasticiser will depend upon whether an aqueous or non-aqueous medium is used, for example suitable plasticisers for an aqueous medium include propylene glycol, triethyl citrate or acetyl triethyl citrate, and for a non-aqueous medium include these and also dibutyl or diethyl phthalate.
- the coating may also include an anti-tack agent such as talc or silica.
- the enteric coating may be applied using an essentially conventional method, for example dissolving or suspending the enteric coating material in the medium, then spraying the solution or suspension onto the granules, followed by drying and screening.
- the granules of this invention may be made up into pharmaceutical formulations in a conventional manner, e.g. by packing into sachets or other containers, or by tabletting, e.g. by a conventional process of compaction to provide a tablet formulation.
- the invention therefore also provides a tablet which includes the above-described granules.
- the invention also provides a process for the use of a granule as described above in the manufacture of a medicament for the treatment of bacterial infections.
- the invention also provides a method of treatment of bacterial infections in humans and animals which comprises the administration of a therapeutically effective amount of granules as described above.
- the invention also provides pharmaceutical granules as described above for use in the treatment of bacterial infections.
- AerosU 200 1.0 Enteric coat
- the first four ingredients were granulated using water and then enteric coated using methylene dichloride/methanol (60/40 v/v).
- the first four ingredients were granulated using methylene dichloride/methanol (70/30 v/v). and then enteric coated using methanol/methylene dichloride (40/60 v/v).
- Amoxycillin trihydrate 4900g Colloidal silica (Aerosil 200) 25g Sodium lauryl sulphate 50g Granulating solution
- Coating The constituents of the coating suspension are mixed until uniform.
- the vessel of a fluidised bed coater previously fitted with a spray gun for co-current application is loaded with 1kg granules.
- the bed is warmed for a few minutes with warm inlet air. Spray the coating suspension untU sufficient coat is applied.
- the constituents of the coating suspension are mixed unt ⁇ uniform using a high shear mixer (e.g. SUverson).
- a high shear mixer e.g. SUverson
- the vessel of a fluid bed granulator having previously been fitted widi a spray gun for co-current application, is loaded with an appropriate weight of marums.
- the bed of marums is warmed for 5 minutes at an air inlet temperature of 40 °C.
- the coating suspension is sprayed at a flow rate of approximately 3 to 4 L per minute at an atomising pressure of 0.2 bar. Sufficient coat is applied so that the coated marums meet the following dissolution requirements.
- the clavulanate is essentially not released at pH 2 and 4 (preferably less than 10% of the clavulanate content being released of this pH), and achieve almost total release (greater than 80% , and preferably greater than 90%) by the end of the test at pH 7.
- the coated marums are dried for 10-15 minutes at 40°C.
- the dried, coated marums are screened and those between 10 and 12 mesh are retained.
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- Engineering & Computer Science (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP95928859A EP0751771A1 (en) | 1994-03-24 | 1995-03-20 | Pharmaceutical formulations containing beta-lactam antibiotics and an alkyl sulphate surfactant |
JP7524382A JPH09510470A (en) | 1994-03-24 | 1995-03-20 | Pharmaceutical formulations containing beta-lactam antibiotics and alkyl sulphate surfactants |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9405856A GB9405856D0 (en) | 1994-03-24 | 1994-03-24 | Pharmaceutical formulation |
GB9405856.7 | 1994-03-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1995025516A1 true WO1995025516A1 (en) | 1995-09-28 |
Family
ID=10752439
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1995/001039 WO1995025516A1 (en) | 1994-03-24 | 1995-03-20 | Pharmaceutical formulations containing beta-lactam antibiotics and an alkyl sulphate surfactant |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP0751771A1 (en) |
JP (1) | JPH09510470A (en) |
GB (1) | GB9405856D0 (en) |
WO (1) | WO1995025516A1 (en) |
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1998035672A1 (en) * | 1997-02-14 | 1998-08-20 | Smithkline Beecham Laboratoires Pharmaceutiques | Pharmaceutical formulations comprising amoxocyllin and clavulanate |
WO1998040054A1 (en) * | 1997-03-12 | 1998-09-17 | Astra Aktiebolag (Publ) | An enteric coated oral dosage form comprising sodium amoxycillin |
WO2001047499A1 (en) * | 1999-12-23 | 2001-07-05 | Smithkline Beecham P.L.C. | Pharmaceutical formulations comprising sodium amoxycillin and potassium clavulanate |
WO2002083129A2 (en) * | 2001-04-12 | 2002-10-24 | Sandoz Gmbh | Pharmaceutical composition comprising clavulanic acid |
US6660299B2 (en) | 1999-04-13 | 2003-12-09 | Beecham Pharmaceuticals Limited | Modified release pharmaceutical formulation comprising amoxycillin |
US6726908B2 (en) | 1995-09-07 | 2004-04-27 | Smithkline Beecham P.L.C. | Pharmaceutical formulation |
US6746692B2 (en) | 1999-04-13 | 2004-06-08 | Beecham Pharmaceuticals (Pte) Limited | Modified release pharmaceutical formulation comprising amoxycillin |
US6756057B2 (en) | 2000-10-12 | 2004-06-29 | Beecham Pharmaceuticals (Pte) Limited | Amoxicillin and potassium clavulanate dosage form |
US6783773B1 (en) | 1999-04-13 | 2004-08-31 | Beecham Pharmaceuticals (Pte) Limited | Composition comprising amoxicillin and potassium clavulanate |
AT412344B (en) * | 2001-04-12 | 2005-01-25 | Sandoz Ag | Pharmaceutical composition useful for reducing rapid degradation of the active ingredient comprises clavulanate, in the form of granulated and hydrophobised particles, and an active ingredient |
US7011849B2 (en) | 2000-10-12 | 2006-03-14 | Beecham Pharmaceuticals (Pte) Limited | Second release phase formulation |
WO2006072577A1 (en) * | 2005-01-07 | 2006-07-13 | Sandoz Ag | Process for preparing granulates comprising amoxicillin |
AT413983B (en) * | 2001-04-12 | 2006-08-15 | Sandoz Ag | Pharmaceutical composition useful for reducing rapid degradation of the active ingredient comprises clavulanate, in the form of granulated and hydrophobised particles, and an active ingredient |
CN112587481A (en) * | 2020-12-28 | 2021-04-02 | 成都中牧生物药业有限公司 | Alkalescent amoxicillin soluble powder and preparation method thereof |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2459014C (en) * | 2001-09-14 | 2010-08-10 | Scolr, Inc. | Amino acid modulated extended release dosage form |
JP2011500811A (en) * | 2007-10-26 | 2011-01-06 | レクサン ファーマシューティカルズ インコーポレイテッド | Clavulanic acid pharmaceutical formulation |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2523446A1 (en) * | 1982-03-19 | 1983-09-23 | Dietlin Francois | Controlled release pharmaceutical compsns. - for oral admin. contg. konjak mannan(s) and surfactant |
US4602012A (en) * | 1984-01-03 | 1986-07-22 | Glaxo Group Limited | Cephalosporin antibiotics |
EP0293975A1 (en) * | 1987-05-27 | 1988-12-07 | Akzo N.V. | Dry, rapidly soluble, compositions of beta-lactam antibiotics |
EP0411952A2 (en) * | 1989-08-04 | 1991-02-06 | McNEIL-PPC, INC. | Rotogranulations and taste masking coatings for preparation of chewable pharmaceutical tablets |
WO1991016893A1 (en) * | 1990-04-27 | 1991-11-14 | Beecham Group Plc | Pharmaceutical formulation |
-
1994
- 1994-03-24 GB GB9405856A patent/GB9405856D0/en active Pending
-
1995
- 1995-03-20 WO PCT/EP1995/001039 patent/WO1995025516A1/en not_active Application Discontinuation
- 1995-03-20 JP JP7524382A patent/JPH09510470A/en active Pending
- 1995-03-20 EP EP95928859A patent/EP0751771A1/en not_active Withdrawn
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2523446A1 (en) * | 1982-03-19 | 1983-09-23 | Dietlin Francois | Controlled release pharmaceutical compsns. - for oral admin. contg. konjak mannan(s) and surfactant |
US4602012A (en) * | 1984-01-03 | 1986-07-22 | Glaxo Group Limited | Cephalosporin antibiotics |
EP0293975A1 (en) * | 1987-05-27 | 1988-12-07 | Akzo N.V. | Dry, rapidly soluble, compositions of beta-lactam antibiotics |
EP0411952A2 (en) * | 1989-08-04 | 1991-02-06 | McNEIL-PPC, INC. | Rotogranulations and taste masking coatings for preparation of chewable pharmaceutical tablets |
WO1991016893A1 (en) * | 1990-04-27 | 1991-11-14 | Beecham Group Plc | Pharmaceutical formulation |
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6726908B2 (en) | 1995-09-07 | 2004-04-27 | Smithkline Beecham P.L.C. | Pharmaceutical formulation |
WO1998035672A1 (en) * | 1997-02-14 | 1998-08-20 | Smithkline Beecham Laboratoires Pharmaceutiques | Pharmaceutical formulations comprising amoxocyllin and clavulanate |
WO1998040054A1 (en) * | 1997-03-12 | 1998-09-17 | Astra Aktiebolag (Publ) | An enteric coated oral dosage form comprising sodium amoxycillin |
US6878386B1 (en) | 1999-04-13 | 2005-04-12 | Beecham Pharmaceuticals (Pte) Limited | Method of treating a bacterial infection comprising amoxycillin and potassium clavulanate |
US7250176B1 (en) | 1999-04-13 | 2007-07-31 | Beecham Pharmaceuticals (Pte) Limited | Method of treating a bacterial infection |
US7217430B2 (en) | 1999-04-13 | 2007-05-15 | Beecham Pharmaceuticals (Pte) Limited | Compositions and methods of treatment comprising amoxicillin and potassium clavulanate with xanthan |
US6660299B2 (en) | 1999-04-13 | 2003-12-09 | Beecham Pharmaceuticals Limited | Modified release pharmaceutical formulation comprising amoxycillin |
US6746692B2 (en) | 1999-04-13 | 2004-06-08 | Beecham Pharmaceuticals (Pte) Limited | Modified release pharmaceutical formulation comprising amoxycillin |
US6783773B1 (en) | 1999-04-13 | 2004-08-31 | Beecham Pharmaceuticals (Pte) Limited | Composition comprising amoxicillin and potassium clavulanate |
WO2001047499A1 (en) * | 1999-12-23 | 2001-07-05 | Smithkline Beecham P.L.C. | Pharmaceutical formulations comprising sodium amoxycillin and potassium clavulanate |
US7011849B2 (en) | 2000-10-12 | 2006-03-14 | Beecham Pharmaceuticals (Pte) Limited | Second release phase formulation |
US6756057B2 (en) | 2000-10-12 | 2004-06-29 | Beecham Pharmaceuticals (Pte) Limited | Amoxicillin and potassium clavulanate dosage form |
AT412344B (en) * | 2001-04-12 | 2005-01-25 | Sandoz Ag | Pharmaceutical composition useful for reducing rapid degradation of the active ingredient comprises clavulanate, in the form of granulated and hydrophobised particles, and an active ingredient |
AT413983B (en) * | 2001-04-12 | 2006-08-15 | Sandoz Ag | Pharmaceutical composition useful for reducing rapid degradation of the active ingredient comprises clavulanate, in the form of granulated and hydrophobised particles, and an active ingredient |
WO2002083129A3 (en) * | 2001-04-12 | 2003-03-06 | Biochemie Gmbh | Pharmaceutical composition comprising clavulanic acid |
WO2002083129A2 (en) * | 2001-04-12 | 2002-10-24 | Sandoz Gmbh | Pharmaceutical composition comprising clavulanic acid |
WO2006072577A1 (en) * | 2005-01-07 | 2006-07-13 | Sandoz Ag | Process for preparing granulates comprising amoxicillin |
CN112587481A (en) * | 2020-12-28 | 2021-04-02 | 成都中牧生物药业有限公司 | Alkalescent amoxicillin soluble powder and preparation method thereof |
CN112587481B (en) * | 2020-12-28 | 2022-03-15 | 成都中牧生物药业有限公司 | Alkalescent amoxicillin soluble powder and preparation method thereof |
Also Published As
Publication number | Publication date |
---|---|
JPH09510470A (en) | 1997-10-21 |
EP0751771A1 (en) | 1997-01-08 |
GB9405856D0 (en) | 1994-05-11 |
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