WO1995028148A1 - Pharmaceutical formulation - Google Patents
Pharmaceutical formulation Download PDFInfo
- Publication number
- WO1995028148A1 WO1995028148A1 PCT/EP1995/001269 EP9501269W WO9528148A1 WO 1995028148 A1 WO1995028148 A1 WO 1995028148A1 EP 9501269 W EP9501269 W EP 9501269W WO 9528148 A1 WO9528148 A1 WO 9528148A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- core
- tablet
- tablet formulation
- clavulanate
- formulation according
- 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
- A61K9/20—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
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
- A61K31/43—Compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula, e.g. penicillins, penems
Definitions
- This invention relates to tablet formulations for oral administration, particularly to formulations, which comprise a ⁇ -lactam antibiotic, optionally together with a ⁇ -lactamase inhibitor.
- a tablet formulation comprises a core which includes a first pharmaceutically active material, the core being coated with a release retarding coating, the coated core being itself surrounded by a casing layer which includes a second pharmaceutically active material.
- the tablet formulation of the invention is suitable for oral administration, and provides a sustained and/or delayed release as a result of initial quick release of the second active material from the casing layer, and a sustained or delayed release of first active material from the coated core.
- the casing layer may serve to protect the core from the ingress of air and atmospheric moisture.
- coating of a single relatively large core in the tablet of the invention with a release-retarding coating requires less coating material than is required to coat a large number of smaller granules, and can therefore lead to a relatively low tablet weight.
- the first and second pharmaceutically active materials in the tablet formulation may each individually, and/or together, comprise a ⁇ -lactam antibiotic optionally together with a ⁇ -lactamase inhibitor.
- the ⁇ -lactam antibiotic may be amoxycillin, e.g. in the form of its trihydrate, optionally together in combination with the ⁇ -lactamase inhibitor clavulanate, (the term "clavulanate” used herein, unless otherwise identified, refers both to clavulanic acid and its salts) e.g. in particular potassium clavulanate.
- the first and second active materials may both comprise the same active material, for example both comprising a ⁇ -lactam antibiotic optionally in combination with a ⁇ -lactamase inhibitor.
- the relative ratios of amoxycillin: clavulanate may be different in the core and the casing layer, making up the overall ratio in the tablet.
- amoxycillin: clavulanate ratios in the core and casing layer and the overall ratio may each vary between broad limits, e.g. between 30:1 to 1:1, typically 12:1 to 2:1.
- a preferred ratio is around 8:1 to 4:1 . ⁇ 25%.
- the quantity of active material(s) in the tablet may vary up to the maximum allowed daily dose, and may typically be around a nominal single unit dose.
- a single tablet may contain around 125, 250, 500, 750 or 875 mg of amoxycillin, and 62.5, 125 or 250 mg of clavulanate, both sets of weights being expressed in terms of the respective free acids.
- the overall tablet may contain nominally 500mg amoxycillin and 125 mg clavulanate, or 875mg amoxycillin and 125 mg of clavulanate. Alternatively these weights may be divided between two or more tablets.
- the core may contain 25-75% of the total weight of the first and second components, and the casing layer may contain 75-25% thereof.
- both the core and the casing layer may contain clavulanate and amoxycillin.
- the core may contain 25-75% of the clavulanate and 25-75% of the amoxycillin, the balance being contained in the casing layer.
- the core may contain 100-400mg of amoxycillin and 30-95mg of clavulanate, expressed as the respective free acids.
- all of the clavulanate may be contained in the casing layer, e.g.
- clavulanate in a rapid release form, with none of the clavulanate contained in the core.
- Such an embodiment may assist in maximising the clavulanate plasma level peak.
- all of the clavulanate may be contained in the core, with none of the clavulanate contained in the casing layer.
- the core may be any convenient shape and need not necessarily be directly related to the shape of the overall tablet, typically the core may be spherical, ellipsoidal, or oblate spheroidal, within any suitable or convenient, e.g. a conventional, tablet shape.
- the core and the casing layer may both comprise a compact of compressed ingredients including the respective active materials such as amoxycillin trihydrate optionally combined with potassium clavulanate.
- the active material(s) in the core may be present in a micronised or solubilised form.
- the core and casing layer may contain additives conventional to the art of compressed tablets.
- Appropriate additives in such a tablet may comprise diluents such as calcium carbonate, magnesium carbonate, dicalcium phosphate or mixtures thereof, binders such as microcrystalline cellulose hydroxypropylmethylcellulose, hydroxypropyl- cellulose, polyvinylpyrrolidone, pre-gelatinised starch or gum acacia or mixtures thereof, disintegrants such as microcrystalline cellulose (fulfilling both binder and disintegrant functions) cross-linked polyvinylpyrrolidone, sodium starch glycollate, croscarmellose sodium or mixtures thereof, lubricants, .such as magnesium stearate or stearic acid, glidants or flow aids, such as colloidal silica, talc or starch, and stabilisers such as desiccating amorphous silica, colouring agents, flavours etc.
- the core and casing layer may contain the same or different additives, in the same or different proportions.
- the core may be made from a compacted mixture of its components, suitably in the form of granules, which may be made by a conventional granulating process as known in the art.
- the granules are made by a procedure of dry granulation of the granule components, for example milling, blending, slugging then milling, or by milling, blending or roller compaction then milling.
- the granules may include conventional additives introduced as a result of the granulation process, e.g. lubricants such as magnesium stearate, in conventional quantities, e.g. ca. 0.5 - 1 wt% of magnesium stearate.
- the granules are of 10 - 80 mesh size, suitably 10-40 mesh size, for example 16 - 30 mesh size.
- the release-retarding coating may be a polymeric material, for example an enteric polymer (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).
- 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).
- An enteric coating may be an essentially conventional coating material, for example enteric polymers such as cellulose acetate phthalate, cellulose acetate succinate, methylcellulose phthalate, ethylhydroxycellulose phthalate, polyvinyl- acetatephthalate, polyvinylbutyrate acetate, vinyl acetate-maleic anhydride copolymer, styrene-maleic mono-ester copolymer, methyl acrylate-methacrylic acid copolymer, methacrylate-methacrylic acid-octyl acrylate copolymer, etc. These may be used either alone or in combination, or together with other polymers than those mentioned above.
- enteric polymers such as cellulose acetate phthalate, cellulose acetate succinate, methylcellulose phthalate, ethylhydroxycellulose phthalate, polyvinyl- acetatephthalate, polyvinylbutyrate acetate, vinyl acetate-maleic anhydride copolymer,
- the enteric coating may also include insoluble substances which are neither decomposed nor solubilized in living bodies, such as alkyl cellulose derivatives such as ethyl cellulose, crosslinked polymers such as styrene- divinylbenzene copolymer, polysaccharides having hydroxyl groups such as dextran, cellulose derivatives which are treated with bifunctional crosslinking agents such as epichlorohydrin, dichlorohydrin, 1, 2-, 3, 4-diepoxybutane, etc.
- the enteric coating may also include starch and/or dextrin.
- Preferred coating materials are the pharmaceutically acceptable methacrylic acid copolymer 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 for example having a solubility in aqueous media at pH 5.5 and above, such as the commercially available "Eudragit” (Trade Mark) enteric polymers, such as “Eudragit L 30" (Trade Mark) i.e. a cationic polymer synthesised from dimemylaminoethyl methacrylate, "Eudragit S” (Trade Mark) and “Eudragit NE” (Trade Mark).
- enteric polymers such as "Eudragit L 30" (Trade Mark) i.e. a cationic polymer synthesised from dimemylaminoethyl methacrylate, "Eudragit S” (Trade Mark) and “Eudragit NE” (Trade Mark).
- enteric polymers such as "Eudragit L 30" (Trade Mark) i.e. a cationic polymer synthesised from dimemylaminoethyl methacrylate, "E
- Aqueous plasticisers include propylene glycol or "Citroflex” or Citroflex A2" (Trade Marks) (mainly triethyl citrate or acetyl triethyl citrate).
- Non-aqueous plasticisers include these, and also diethyl and dibutyl phthalate and dibutyl sebacate.
- the quantity of plasticiser included will be apparent to those skilled in the art.
- the enteric coating may also include an anti-tack agent such as talc, silica or glyceryl monostearate.
- the quantity of plasticiser and anti-tack agent may be generally conventional to the art.
- the coating may include around 10 - 25 wt. % plasticiser and up to around 50 wt% of anti tack agent, e.g. 5 - 20 wt. % of anti-tack agent.
- An enteric coating may be applied to the core by dissolving or suspending the enteric coating materials in a suitable medium, such as water, methanol, ethanol, isopropanol, acetone, methyl ethyl ketone, methylene chloride, ethylene chloride, ethyl acetate, etc. or mixtures thereof, and the resultant solution or suspension may be sprayed on the core to coat them, followed by drying sufficiently with an air flow and screening.
- a suitable medium such as water, methanol, ethanol, isopropanol, acetone, methyl ethyl ketone, methylene chloride, ethylene chloride, ethyl acetate, etc. or mixtures thereof.
- the enteric coating material may be dissolved or suspended in a solvent for example water and coated onto the core using a fluidised bed system. If water is used, preferably an anti-foaming agent such as activated polymethylsiloxane is also included.
- Suitable sub-coat materials include hydroxypropylmethyl cellulose, for example of the known types E5 and E15 (Trade Marks) in mixture. It may also be desirable to apply one or more over-coats after application of the release retarding coating layer, the over-coat consequently lying over the release retarding coating.
- Suitable over ⁇ coat materials include copolymers of methacrylic acid and methyl methacrylate, and hydroxypropylmethyl cellulose. The over-coat may be of the same material as the sub-coat. Typically such coatings may be applied by known techniques of aqueous film coating.
- the casing layer may be applied to the coated core by a generally conventional process in which the coated core is encased in a mass of the powdered or granulated casing material components.
- the granules of such a casing material may be made by a conventional granulating process as known in the art, and as discussed above with reference to the manufacture of the core granules.
- the casing layer itself may be coated with a final outer coating, for example of hydroxypropyl methyl cellulose, which may be applied by known film coating techniques in a similar manner to the way in which the sub-and over-coats may be applied to the core.
- the tablet of the invention offers the advantages effect that the active material in the casing layer is released initially in the stomach, and the coated core releases its active material content more slowly. In this way as in vivo decay of the initially released material occurs, active material is subsequently released from the core to provide an extended blood level profile. If the release-retarding coating on the core is an enteric coating the release of active material from the core may occur in the intestine.
- the invention therefore also provides a method of preparing a pharmaceutical formulation as described herein, comprising the steps of forming a core which includes a first pharmaceutically active material, the core being coated with a release-retarding coating, then coating the core with a casing layer which includes a second pharmaceutically active material.
- Clavulanic acid and its derivatives e.g. salts such as potassium clavulanate are extremely moisture sensitive, and all operations carried out to prepare granules and formulations of this invention which contain clavulanate should be carried out under conditions of low relative humidity, e.g. less than 30% RH, ideally as low as practical.
- the present invention also provides a pharmaceutical formulation as described herein for use as an active therapeutic substance.
- the present invention also provides a pharmaceutical formulation as described herein for use in the treatment of bacterial infections.
- the present invention also provides the use of a formulation as described herein in the manufacture of a medicament for use in the treatment of bacterial infections.
- the present invention also provides a method of treatment of bacterial infections in humans or animals which comprises the administration of an effective amount of a pharmaceutical formulation as described herein.
- a tablet (overall (1)) comprises a core (2), which is coated with successively a sub-coat (3), an enteric coat (4), and an over-coat (5).
- the coated core (2-5) is itself encased within a casing layer (6) forming the overall shape of the tablet (1), and the casing layer (6) is itself coated with a protective film coat (7).
- the relative sizes of the core (2) and tablet (1), and the thickness of the coating layers (3), (4), (5), (6), (7) are not to scale but merely illustrative.
- Example 1 Example 1
- Tablets 1 and 2 were prepared respectively being tablets containing nominally 500mg and 875mg of amoxycillin as the trihydrate, both tablets containing 125mg of clavulanate, as potassium clavulanate.
- the core for tablets 1 and 2 had the same composition and was made by the same procedure. Their formulation was as below: Component mg % % Range*
- the Polyplasdone XL dried is present as a disintegrant.
- the Syloid AL1 is a desiccant to prevent hydrolytic degradation of the actives.
- the magnesium stearate is present as a lubricant.
- the microcrystalline cellulose is a tablet binder and disintegrant.
- the % range column suggests suitable % ranges for the components listed.
- the cores were made by the following process:
- the milled amoxycillin trihydrate was mixed with the potassium clavulanate, Polyplasdone, Syloid AL1, part of the magnesium stearate, and part of the microcrystalline cellulose.
- Microcrystalline Cellulose 5.0 2.1 Granules from 1.4 were blended with remaining Magnesium Stearate and remaining Microcrystalline cellulose. -
- the cores were manufactured from the compression mix prepared in 2.1 to a core weight of 450mg, and a hardness of 15-20Kp Schleuniger. 2.3 The cores were then film sub-coated with an aqueous suspension of hydroxypropyl methyl cellulose, further coated with an Eudragit enteric coating and finally, with a ftirther over-coating of hydroxypropyl methyl cellulose.
- An enteric coat weight of 21.2mg was applied to the core.
- a 5mg/tablet final over-coat of the cores with a hydroxypropyl methyl cellulose coating was applied.
- the three film coats were applied to the core using low humidity conditions to effect rapid drying, in a coating drum (Accelacota, Driam or Hicota), using an intermittent air spray process.
- the casing layer was applied to the cores by the following process: 1. Granulation of casing material.
- amoxycillin trihydrate was milled using a swing hammer mill at fast speed through an 0.063 inch screen with knives forward.
- amoxycillin trihydrate was blended with the potassium clavulanate, Polyplasdone, Syloid AL1 and part of the magnesium stearate and part of the microcrystalline cellulose.
- the cores were fed to a specially designed tablet press, e.g. a Kilian RX machine adapted for core tablet manufacture, which dosed the compression mix 'tablet casing' and a core into the tablet die followed by a further quantity of compression mix 'tablet casing' and the total core/compression mix was compressed to form a 1130mg tablet.
- the tablet press was designed to reject tablets which do not contain a core. Alternatively individual tablets could be made by hand.
- the tablet was aqueous film coated using a Hydroxypropl Methyl Cellulose aqueous film coat, applying 27mg of coat to the tablet.
- This process was carried out in a coating drum, e.g. Accelacota, Driam or Hicota, using an air spray process.
- the casing layer material was prepared by a slugging or roller compaction process as described with respect to Tablet 1 above.
- the compression mix and cores were fed to a designed core tablet press equipped to reject tablets which do not contain a core.
- tablets could be made individually by a hand press.
- the tablets each containing a core were aqueous film coated in a drum coating unit, e.g. an Accelacota, Driam or Hicota with a Hydroxypropl Methyl Cellulose Suspension to a film coat weight of 32mg.
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP7526673A JPH09511994A (en) | 1994-04-14 | 1995-04-07 | Pharmaceutical prescription |
DE69525148T DE69525148T2 (en) | 1994-04-14 | 1995-04-07 | PHARMACEUTICAL FORMULATION |
US08/718,550 US6136345A (en) | 1994-04-14 | 1995-04-07 | Tablet containing a coated core |
EP95915856A EP0752850B1 (en) | 1994-04-14 | 1995-04-07 | Pharmaceutical formulation |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9407386A GB9407386D0 (en) | 1994-04-14 | 1994-04-14 | Pharmaceutical formulation |
GB9407386.3 | 1994-04-14 |
Related Child Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US08/718,550 A-371-Of-International US6136345A (en) | 1994-04-14 | 1995-04-07 | Tablet containing a coated core |
US08718550 A-371-Of-International | 1995-04-07 | ||
US09/640,823 Division US6358528B1 (en) | 1994-04-14 | 2000-08-17 | Pharmaceutical formulation |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1995028148A1 true WO1995028148A1 (en) | 1995-10-26 |
Family
ID=10753514
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1995/001269 WO1995028148A1 (en) | 1994-04-14 | 1995-04-07 | Pharmaceutical formulation |
Country Status (6)
Country | Link |
---|---|
US (3) | US6136345A (en) |
EP (1) | EP0752850B1 (en) |
JP (1) | JPH09511994A (en) |
DE (1) | DE69525148T2 (en) |
GB (1) | GB9407386D0 (en) |
WO (1) | WO1995028148A1 (en) |
Cited By (24)
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 |
EP1025841A1 (en) * | 1994-02-04 | 2000-08-09 | Smithkline Beecham Plc | Bilayered amoxycillin tablets |
EP1044680A1 (en) * | 1999-04-13 | 2000-10-18 | Beecham Pharmaceuticals (Pte) Limited | Novel method of treatment using a high dosage regimen of amoxycillin and potassium clavulanate |
US6294199B1 (en) | 1999-04-13 | 2001-09-25 | Beecham Pharmaceuticals (Pte) Limited | Method of treating a bacterial infection comprising administering amoxycillin |
US6299903B1 (en) * | 1994-08-17 | 2001-10-09 | Smithkline Beecham P.L.C. | Delayed release pharmaceutical formulation containing a β-lactam antibiotic |
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 |
WO2005030179A1 (en) * | 2003-09-29 | 2005-04-07 | Cj Corporation | Sustained-release formulations |
KR100502478B1 (en) * | 1997-06-13 | 2005-12-02 | 동아제약주식회사 | Pharmaceutical composition for treating bacterial infections containing clavulanic acid and betalactam antibiotics |
US7011849B2 (en) | 2000-10-12 | 2006-03-14 | Beecham Pharmaceuticals (Pte) Limited | Second release phase formulation |
JP2007126478A (en) * | 1997-05-30 | 2007-05-24 | Osmotica Corp | Multi-layered permeation device |
WO2007059916A2 (en) * | 2005-11-23 | 2007-05-31 | Sandoz Ag | Pharmaceutical composition |
US7838032B2 (en) | 2000-04-28 | 2010-11-23 | Reckitt Benckiser Inc. | Sustained release of guaifenesin |
US7985421B2 (en) | 2000-04-28 | 2011-07-26 | Reckitt Benckiser Inc. | Sustained release formulations of guaifenesin and additional drug ingredients |
US7985420B2 (en) | 2000-04-28 | 2011-07-26 | Reckitt Benckiser Inc. | Sustained release of guaifenesin combination drugs |
US8012504B2 (en) | 2000-04-28 | 2011-09-06 | Reckitt Benckiser Inc. | Sustained release of guaifenesin combination drugs |
WO2013057569A3 (en) * | 2011-10-19 | 2013-07-04 | Micro Labs Limited | Extended release pharmaceutical composition containing amoxicillin and clavulanic acid |
US8889187B2 (en) * | 2000-02-24 | 2014-11-18 | Shionogi Inc. | Once a day amoxicillin product comprising immediate and delayed release dosage forms |
US9801827B2 (en) | 2006-03-06 | 2017-10-31 | Pozen Inc. | Dosage forms for administering combinations of drugs |
US11020402B2 (en) | 2018-10-15 | 2021-06-01 | Axsome Therapeutics, Inc. | Use of reboxetine to treat narcolepsy |
US11278506B2 (en) | 2015-10-09 | 2022-03-22 | Rb Health (Us) Llc | Pharmaceutical formulation |
US11351175B2 (en) | 2018-10-15 | 2022-06-07 | Axsome Therapeutics, Inc. | Use of reboxetine to treat narcolepsy |
Families Citing this family (81)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20030109503A1 (en) * | 1995-06-06 | 2003-06-12 | Smithkline Beecham P.L.C. | Pharmaceutical formulations comprising clavulanic acid alone or in combination with other beta-lactam antibiotics |
US8071128B2 (en) | 1996-06-14 | 2011-12-06 | Kyowa Hakko Kirin Co., Ltd. | Intrabuccally rapidly disintegrating tablet and a production method of the tablets |
AUPS270602A0 (en) | 2002-05-31 | 2002-06-20 | Baron, Peter | Drink flavouring straw |
US20030087005A1 (en) * | 1996-10-10 | 2003-05-08 | Peter Baron | Drink flavouring straw |
US20030124187A1 (en) * | 1997-02-14 | 2003-07-03 | Smithkline Beecham Laboratoires Pharmaceutiques, | Pharmaceutical formulations comprising amoxycillin and clavulanate |
EP1265599A4 (en) * | 2000-02-24 | 2006-01-18 | Advancis Pharmaceutical Corp | Antibiotic composition with inhibitor |
AU2001239869B2 (en) * | 2000-02-24 | 2005-12-15 | Shionogi, Inc. | Antibiotic composition with inhibitor |
US6565882B2 (en) * | 2000-02-24 | 2003-05-20 | Advancis Pharmaceutical Corp | Antibiotic composition with inhibitor |
US20020068078A1 (en) | 2000-10-13 | 2002-06-06 | Rudnic Edward M. | Antifungal product, use and formulation thereof |
US6541014B2 (en) * | 2000-10-13 | 2003-04-01 | Advancis Pharmaceutical Corp. | Antiviral product, use and formulation thereof |
GB0025208D0 (en) * | 2000-10-13 | 2000-11-29 | Euro Celtique Sa | Delayed release pharmaceutical formulations |
US20020197314A1 (en) * | 2001-02-23 | 2002-12-26 | Rudnic Edward M. | Anti-fungal composition |
US20030143272A1 (en) * | 2001-03-14 | 2003-07-31 | Waterman Kenneth C. | Pharmaceutical tablet and process for making thereof |
DE60212475T2 (en) * | 2001-03-14 | 2007-07-05 | Pfizer Products Inc., Groton | Pharmaceutical tablet and a process for its preparation |
US9358214B2 (en) | 2001-10-04 | 2016-06-07 | Adare Pharmaceuticals, Inc. | Timed, sustained release systems for propranolol |
US7560123B2 (en) | 2004-08-12 | 2009-07-14 | Everett Laboratories, Inc. | Compositions and methods for nutrition supplementation |
KR100540035B1 (en) * | 2002-02-01 | 2005-12-29 | 주식회사 태평양 | Multi-stage oral drug controlled-release system |
WO2003096874A2 (en) * | 2002-05-15 | 2003-11-27 | Sun Pharmaceutical Industries Limited | Coated sustained release tablets of a hygroscopic compound for once-a-day therapy |
KR100456833B1 (en) * | 2002-08-01 | 2004-11-10 | 주식회사 대웅 | Cored tablets containing amoxycillin and clavulanate |
SI1894562T1 (en) * | 2002-08-15 | 2011-04-29 | Euro Celtique Sa | Pharmaceutical compositions comprising an opioid antagonist |
US6803046B2 (en) | 2002-08-16 | 2004-10-12 | Bracco International B.V. | Sincalide formulations |
US6814983B2 (en) * | 2002-12-10 | 2004-11-09 | Everett Laboratories, Inc. | Compositions and methods for nutrition supplementation |
US8617617B2 (en) * | 2002-12-10 | 2013-12-31 | Everett Laboratories, Inc. | Methods and kits for co-administration of nutritional supplements |
US8367111B2 (en) | 2002-12-31 | 2013-02-05 | Aptalis Pharmatech, Inc. | Extended release dosage forms of propranolol hydrochloride |
EP1596841B1 (en) * | 2003-02-21 | 2008-10-08 | LEK Pharmaceuticals D.D. | Therapeutic system comprising amoxicillin and clavulanic acid |
MXPA05011724A (en) * | 2003-05-02 | 2006-01-23 | Warner Lambert Co | Confectionery products for delivery of pharmaceutically active agents to the throat. |
AU2004258949B2 (en) * | 2003-07-21 | 2011-02-10 | Shionogi, Inc. | Antibiotic product, use and formulation thereof |
EP1648418A4 (en) * | 2003-07-21 | 2011-11-16 | Middlebrook Pharmaceuticals Inc | Antibiotic product, use and formulation thereof |
CA2533292C (en) * | 2003-07-21 | 2013-12-31 | Advancis Pharmaceutical Corporation | Antibiotic product, use and formulation thereof |
JP2007502296A (en) * | 2003-08-11 | 2007-02-08 | アドバンシス ファーマスーティカル コーポレイション | Robust pellet |
AU2004264356B2 (en) | 2003-08-12 | 2011-01-27 | Shionogi, Inc. | Antibiotic product, use and formulation thereof |
US8246996B2 (en) * | 2003-08-29 | 2012-08-21 | Shionogi Inc. | Antibiotic product, use and formulation thereof |
US8460710B2 (en) * | 2003-09-15 | 2013-06-11 | Shionogi, Inc. | Antibiotic product, use and formulation thereof |
EP1708684A2 (en) | 2003-09-26 | 2006-10-11 | Alza Corporation | Drug coating providing high drug loading and methods for providing the same |
NZ546183A (en) * | 2003-09-26 | 2011-04-29 | Alza Corp | Controlled release formulations exhibiting an ascending rate of release |
US20050142187A1 (en) * | 2003-12-24 | 2005-06-30 | Treacy Donald J.Jr. | Enhanced absorption of modified release dosage forms |
TW200534879A (en) * | 2004-03-25 | 2005-11-01 | Bristol Myers Squibb Co | Coated tablet formulation and method |
US7829720B2 (en) * | 2004-05-04 | 2010-11-09 | Bristol-Myers Squibb Company | Process for preparing atazanavir bisulfate and novel forms |
US20050256314A1 (en) * | 2004-05-04 | 2005-11-17 | Soojin Kim | Process employing controlled crystallization in forming crystals of a pharmaceutical |
US20050288343A1 (en) * | 2004-05-19 | 2005-12-29 | Andrew Rusowicz | Process of preparing substituted carbamates and intermediates thereof |
TWI354569B (en) | 2004-05-28 | 2011-12-21 | Bristol Myers Squibb Co | Coated tablet formulation and method |
EP1771158A4 (en) * | 2004-07-02 | 2008-03-12 | Advancis Pharmaceutical Corp | Tablet for pulsed delivery |
KR100638315B1 (en) * | 2004-07-23 | 2006-10-25 | 주식회사 대웅제약 | Cored tablets comprising clavulanate and amoxycilin with multiple film coated core layer |
DE102004035938A1 (en) * | 2004-07-23 | 2006-02-16 | Röhm GmbH & Co. KG | Process for the preparation of coated drug forms with stable drug release profile |
US8101587B2 (en) | 2004-08-12 | 2012-01-24 | Everett Laboratories, Inc. | Kits for nutrition supplementation |
US8747895B2 (en) | 2004-09-13 | 2014-06-10 | Aptalis Pharmatech, Inc. | Orally disintegrating tablets of atomoxetine |
US8541026B2 (en) | 2004-09-24 | 2013-09-24 | Abbvie Inc. | Sustained release formulations of opioid and nonopioid analgesics |
US9884014B2 (en) | 2004-10-12 | 2018-02-06 | Adare Pharmaceuticals, Inc. | Taste-masked pharmaceutical compositions |
ES2409347T3 (en) | 2004-10-21 | 2013-06-26 | Aptalis Pharmatech, Inc. | Pharmaceutical compositions of masked flavor with gastro-soluble porogenic agents |
EP1681050A1 (en) * | 2005-01-13 | 2006-07-19 | Strides Arcolab Limited | Dispersible sustained release pharmaceutical compositions |
US9161918B2 (en) | 2005-05-02 | 2015-10-20 | Adare Pharmaceuticals, Inc. | Timed, pulsatile release systems |
ATE438381T1 (en) * | 2005-11-18 | 2009-08-15 | Synhton B V | ZOLPIDEME TABLETS |
US8357394B2 (en) | 2005-12-08 | 2013-01-22 | Shionogi Inc. | Compositions and methods for improved efficacy of penicillin-type antibiotics |
US8778924B2 (en) * | 2006-12-04 | 2014-07-15 | Shionogi Inc. | Modified release amoxicillin products |
AR060029A1 (en) | 2006-03-02 | 2008-05-21 | Unistraw Patent Holdings Ltd | DRINK STRAW ADAPTED FOR PROGRESSIVELY CONDITIONING AN ACTIVE INGREDIENT AND METHOD OF MANUFACTURING SUCH PAJILLA |
EA020867B1 (en) * | 2006-03-06 | 2015-02-27 | Поузен Инк. | Dosage forms for administering combinations of drugs |
US8299052B2 (en) | 2006-05-05 | 2012-10-30 | Shionogi Inc. | Pharmaceutical compositions and methods for improved bacterial eradication |
US8765178B2 (en) * | 2006-07-19 | 2014-07-01 | Watson Laboratories, Inc. | Controlled release formulations and associated methods |
WO2008029351A2 (en) * | 2006-09-04 | 2008-03-13 | Ranbaxy Laboratories Limited | A modified release formulation comprising amoxicillin and clavulanate |
BRPI0719280A2 (en) | 2006-11-27 | 2014-03-11 | Lundbeck & Co As H | COMPOUND, PHARMACEUTICAL COMPOSITION, METHODS FOR MODULATING THE ACTIVITY OF A P2X7 IN VITRO RECEIVER AND IN A PATIENT, TO TREAT A CONDITION RESPONSIBLE FOR P2X7 RECEIVER MODULATION IN A PATIENT, TO INHIBIT THE DEVELOPMENT OF A GALLULLE CELL IN A PITCH TO DETERMINE THE PRESENCE OR ABSENCE OF P2X7 RECEIVER IN A SAMPLE, PACKAGED PHARMACEUTICAL PREPARATION, METHOD FOR TREATING OR PREVENTING CIRROSIS IN A PATIENT, AND USING A COMPOUND. |
KR20100033379A (en) * | 2007-06-22 | 2010-03-29 | 브리스톨-마이어스 스큅 컴퍼니 | Tableted compositions containing atazanavir |
EP2170292B1 (en) * | 2007-06-22 | 2014-01-08 | Bristol-Myers Squibb Holdings Ireland | Tableted compositions containing atazanavir |
KR20100033378A (en) * | 2007-06-22 | 2010-03-29 | 브리스톨-마이어스 스큅 컴퍼니 | Tableted compositions containing atazanavir |
PT2178513E (en) * | 2007-06-22 | 2011-05-31 | Bristol Myers Squibb Co | Tableted compositions containing atazanavir |
US8807070B2 (en) * | 2008-08-07 | 2014-08-19 | Vector Corporation | Rotor processor for dry powders |
US20100034968A1 (en) * | 2008-08-07 | 2010-02-11 | Vector Corporation | Polymer coating process using dry glidant in a rotor processor |
CA3121471A1 (en) | 2009-05-12 | 2010-11-18 | The Government Of The United States Of America, As Represented By The Secretary, Department Of Health And Human Services, Centers For Disease Control And Prevention | New human rotavirus strains and vaccines |
US8709477B2 (en) * | 2009-08-13 | 2014-04-29 | Kremers Urban Pharmaceuticals, Inc` | Pharmaceutical dosage form |
US9173860B2 (en) * | 2009-11-04 | 2015-11-03 | Susan Park Perrine | S isomers of α-methyl hydrocinnamic acid for the treatment of blood disorders |
EP2506836B1 (en) | 2009-12-02 | 2018-02-14 | Adare Pharmaceuticals S.R.L. | Fexofenadine microcapsules and compositions containing them |
CA2780347A1 (en) * | 2009-12-07 | 2011-06-16 | Mcneil-Ppc, Inc. | Partial dip coating of dosage forms for modified release |
US9682132B2 (en) | 2010-01-26 | 2017-06-20 | Banyan Biomarkers, Inc | Compositions and methods relating to argininosucccinate synthetase |
RS60186B1 (en) | 2011-04-29 | 2020-06-30 | Penn State Res Found | Small molecule trail gene induction by normal and tumor cells as an anticancer therapy |
US8889672B2 (en) | 2011-04-29 | 2014-11-18 | The Regents Of The University Of Michigan | Compounds, formulations, and methods of protein kinase C inhibition |
US8183227B1 (en) | 2011-07-07 | 2012-05-22 | Chemo S. A. France | Compositions, kits and methods for nutrition supplementation |
US8168611B1 (en) | 2011-09-29 | 2012-05-01 | Chemo S.A. France | Compositions, kits and methods for nutrition supplementation |
WO2013149258A2 (en) | 2012-03-30 | 2013-10-03 | Charles Drew University of Medicine and Science | Compositions and methods for treating or preventing metabolic syndrome disorders |
KR20150099588A (en) | 2012-12-20 | 2015-08-31 | 더 펜 스테이트 리서어치 파운데이션 | Methods and compositions relating to treatment of cancer |
US20140271923A1 (en) | 2013-03-14 | 2014-09-18 | Christopher Brian Reid | Compositions & formulations for preventing and treating chronic diseases that cluster in patients such as cardiovascular disease, diabetes, obesity, polycystic ovary syndrome, hyperlipidemia and hypertension, as well as for preventing and treating other diseases and conditions |
WO2015089416A1 (en) | 2013-12-12 | 2015-06-18 | Cornell University | Prolylhydroxylase/atf4 inhibitors for treating neural cell injury |
US11110063B2 (en) | 2017-08-25 | 2021-09-07 | MAIA Pharmaceuticals, Inc. | Storage stable sincalide formulations |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3279997A (en) * | 1963-10-22 | 1966-10-18 | Herbert D Schneyer | Enteric coated calcium lactate tablets containing an antihistamine and thiamine chloride |
WO1994006416A1 (en) * | 1992-09-24 | 1994-03-31 | Jagotec Ag | Pharmaceutical tablet capable of liberating one or more drugs at different release rates |
Family Cites Families (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2470599A1 (en) | 1979-12-07 | 1981-06-12 | Panoz Donald | IMPROVEMENTS IN PROCESSES FOR THE PREPARATION OF GALENIC SHAPES WITH DELAYED ACTION AND PROGRAMMED RELEASE AND GALENIC FORMS OF MEDICAMENTS THUS OBTAINED |
US4525339A (en) * | 1982-10-15 | 1985-06-25 | Hoffmann-La Roche Inc. | Enteric coated oral dosage form |
US4775536A (en) * | 1986-02-24 | 1988-10-04 | Bristol-Myers Company | Enteric coated tablet and process for making |
US5277916A (en) * | 1988-02-01 | 1994-01-11 | F. H. Faulding & Co., Ltd. | Tetracycline dosage form |
DE3814532A1 (en) * | 1988-04-29 | 1989-11-09 | Bayer Ag | DHP-RETARD-PREPARATION |
US5158777A (en) * | 1990-02-16 | 1992-10-27 | E. R. Squibb & Sons, Inc. | Captopril formulation providing increased duration of activity |
FI93924C (en) | 1991-09-17 | 1995-06-26 | Martti Lauri Antero Marvola | A method of preparing a controlled release formulation |
US5407686A (en) * | 1991-11-27 | 1995-04-18 | Sidmak Laboratories, Inc. | Sustained release composition for oral administration of active ingredient |
IL109770A0 (en) | 1993-05-29 | 1994-11-28 | Smithkline Beecham Corp | Thermal infusion process for preparing controlled release solid dosage forms of medicaments for oral administration and controlled release solid dosage forms of medicaments prepared thereby |
IT1264517B1 (en) | 1993-05-31 | 1996-09-24 | Ekita Investments Nv | PHARMACEUTICAL TABLET SUITABLE FOR THE RELEASE IN SUBSEQUENT TIMES OF THE ACTIVE PRINCIPLES CARRIED THEREIN |
IT1264696B1 (en) | 1993-07-09 | 1996-10-04 | Applied Pharma Res | PHARMACEUTICAL FORMS INTENDED FOR ORAL ADMINISTRATION ABLE TO RELEASE ACTIVE SUBSTANCES AT A CONTROLLED AND DIFFERENTIATED SPEED |
US6183778B1 (en) | 1993-09-21 | 2001-02-06 | Jagotec Ag | Pharmaceutical tablet capable of liberating one or more drugs at different release rates |
US6210714B1 (en) | 1993-11-23 | 2001-04-03 | Euro-Celtique S.A. | Immediate release tablet cores of acetaminophen having sustained-release coating |
US5500227A (en) | 1993-11-23 | 1996-03-19 | Euro-Celtique, S.A. | Immediate release tablet cores of insoluble drugs having sustained-release coating |
GB9402203D0 (en) | 1994-02-04 | 1994-03-30 | Smithkline Beecham Plc | Pharmaceutical formulation |
GB9408117D0 (en) | 1994-04-23 | 1994-06-15 | Smithkline Beecham Corp | Pharmaceutical formulations |
GB9416599D0 (en) | 1994-08-17 | 1994-10-12 | Smithkline Beecham Plc | Pharmaceutical formulation |
GB9416600D0 (en) | 1994-08-17 | 1994-10-12 | Smithkline Beecham Plc | Pharmaceutical formulation |
IL139728A (en) | 1995-01-09 | 2003-06-24 | Penwest Pharmaceuticals Compan | Aqueous slurry composition containing microcrystalline cellulose for preparing a pharmaceutical excipient |
US5558879A (en) * | 1995-04-28 | 1996-09-24 | Andrx Pharmaceuticals, Inc. | Controlled release formulation for water soluble drugs in which a passageway is formed in situ |
IT1289160B1 (en) | 1997-01-08 | 1998-09-29 | Jagotec Ag | FULLY COATED PHARMACEUTICAL TABLET FOR THE CONTROLLED RELEASE OF ACTIVE INGREDIENTS WHICH PRESENT PROBLEMS OF |
FR2772615B1 (en) | 1997-12-23 | 2002-06-14 | Lipha | MULTILAYER TABLET FOR INSTANT RELEASE THEN PROLONGED ACTIVE SUBSTANCES |
US6099859A (en) | 1998-03-20 | 2000-08-08 | Andrx Pharmaceuticals, Inc. | Controlled release oral tablet having a unitary core |
FR2784583B1 (en) | 1998-10-16 | 2002-01-25 | Synthelabo | PHARMACEUTICAL COMPOSITION WITH GASTRIC RESIDENCE AND CONTROLLED RELEASE |
US6294199B1 (en) | 1999-04-13 | 2001-09-25 | Beecham Pharmaceuticals (Pte) Limited | Method of treating a bacterial infection comprising administering amoxycillin |
AP1806A (en) | 1999-04-13 | 2007-12-14 | Beecham Pharmaceuticals Pte Ltd | The use of a high dosage regimen of amoxycillin and potassium chavulate for the treatment of bacterial infections. |
-
1994
- 1994-04-14 GB GB9407386A patent/GB9407386D0/en active Pending
-
1995
- 1995-04-07 US US08/718,550 patent/US6136345A/en not_active Expired - Lifetime
- 1995-04-07 DE DE69525148T patent/DE69525148T2/en not_active Expired - Fee Related
- 1995-04-07 JP JP7526673A patent/JPH09511994A/en not_active Ceased
- 1995-04-07 EP EP95915856A patent/EP0752850B1/en not_active Expired - Lifetime
- 1995-04-07 WO PCT/EP1995/001269 patent/WO1995028148A1/en active IP Right Grant
-
2000
- 2000-08-17 US US09/640,823 patent/US6358528B1/en not_active Expired - Lifetime
-
2001
- 2001-12-18 US US10/023,614 patent/US6838094B2/en not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3279997A (en) * | 1963-10-22 | 1966-10-18 | Herbert D Schneyer | Enteric coated calcium lactate tablets containing an antihistamine and thiamine chloride |
WO1994006416A1 (en) * | 1992-09-24 | 1994-03-31 | Jagotec Ag | Pharmaceutical tablet capable of liberating one or more drugs at different release rates |
Cited By (47)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1025841A1 (en) * | 1994-02-04 | 2000-08-09 | Smithkline Beecham Plc | Bilayered amoxycillin tablets |
US6299903B1 (en) * | 1994-08-17 | 2001-10-09 | Smithkline Beecham P.L.C. | Delayed release pharmaceutical formulation containing a β-lactam antibiotic |
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 |
AU728526B2 (en) * | 1997-02-14 | 2001-01-11 | Smithkline Beecham Corporation | Pharmaceutical formulations comprising amoxocyllin and clavulanate |
EP1142574A1 (en) * | 1997-02-14 | 2001-10-10 | Smithkline Beecham Laboratoires Pharmaceutiques | Pharmaceutical formulations comprising amoxycillin and clavulanate |
JP2007126478A (en) * | 1997-05-30 | 2007-05-24 | Osmotica Corp | Multi-layered permeation device |
KR100502478B1 (en) * | 1997-06-13 | 2005-12-02 | 동아제약주식회사 | Pharmaceutical composition for treating bacterial infections containing clavulanic acid and betalactam antibiotics |
JP2002541187A (en) * | 1999-04-13 | 2002-12-03 | ビーチャム・ファーマシューティカルズ・(プライベイト)・リミテッド | New treatment |
US6746692B2 (en) | 1999-04-13 | 2004-06-08 | Beecham Pharmaceuticals (Pte) Limited | Modified release pharmaceutical formulation comprising amoxycillin |
GR1003560B (en) * | 1999-04-13 | 2001-03-16 | Beecham Pharmaceuticals (Pte) Limited | Modified release formulations of amoxycillin and potassium clavulanate |
GB2351661B (en) * | 1999-04-13 | 2001-10-10 | Beecham Pharma | Novel method of treatment |
NL1014915C2 (en) * | 1999-04-13 | 2001-02-12 | Beecham Pharm Pte Ltd | New treatment method. |
BE1013309A5 (en) * | 1999-04-13 | 2001-11-06 | Beecham Pharm Pte Ltd | Pharmaceutical Formulations NEWS INCLUDING THE CLAVULANATE amoxycillin and Potassium. |
US7250176B1 (en) | 1999-04-13 | 2007-07-31 | Beecham Pharmaceuticals (Pte) Limited | Method of treating a bacterial infection |
ES2190692A1 (en) * | 1999-04-13 | 2003-08-01 | Beecham Pharm Pte Ltd | Novel method of treatment using a high dosage regimen of amoxycillin and potassium clavulanate |
AU767177B2 (en) * | 1999-04-13 | 2003-11-06 | Beecham Pharmaceuticals (Pte) Limited | Novel method of treatment |
US6660299B2 (en) | 1999-04-13 | 2003-12-09 | Beecham Pharmaceuticals Limited | Modified release pharmaceutical formulation comprising amoxycillin |
WO2000061116A3 (en) * | 1999-04-13 | 2001-02-01 | Beecham Pharm Pte Ltd | Pharmaceutical formulation comprising amoxycillin and clavulanate |
US6294199B1 (en) | 1999-04-13 | 2001-09-25 | Beecham Pharmaceuticals (Pte) Limited | Method of treating a bacterial infection comprising administering amoxycillin |
AP1806A (en) * | 1999-04-13 | 2007-12-14 | Beecham Pharmaceuticals Pte Ltd | The use of a high dosage regimen of amoxycillin and potassium chavulate for the treatment of bacterial infections. |
US6783773B1 (en) | 1999-04-13 | 2004-08-31 | Beecham Pharmaceuticals (Pte) Limited | Composition comprising amoxicillin and potassium clavulanate |
JP4880125B2 (en) * | 1999-04-13 | 2012-02-22 | ビーチャム・ファーマシューティカルズ・(プライベイト)・リミテッド | New treatment |
US6878386B1 (en) | 1999-04-13 | 2005-04-12 | Beecham Pharmaceuticals (Pte) Limited | Method of treating a bacterial infection comprising amoxycillin and potassium clavulanate |
FR2792198A1 (en) * | 1999-04-13 | 2000-10-20 | Beecham Pharm Pte Ltd | NOVEL PHARMACEUTICAL FORMULATIONS COMPRISING AMOXYCILLIN AND POTASSIUM CLAVULANATE |
WO2000061116A2 (en) * | 1999-04-13 | 2000-10-19 | Beecham Pharmaceuticals (Pte) Limited | Pharmaceutical formulation comprising amoxycillin and clavulanate |
BG65006B1 (en) * | 1999-04-13 | 2006-12-29 | Beecham Pharmaceuticals (Pte) Limited | Phrmacetical forms containing high amoxylin and potassium clavulant doses |
US7217430B2 (en) | 1999-04-13 | 2007-05-15 | Beecham Pharmaceuticals (Pte) Limited | Compositions and methods of treatment comprising amoxicillin and potassium clavulanate with xanthan |
EP1044680A1 (en) * | 1999-04-13 | 2000-10-18 | Beecham Pharmaceuticals (Pte) Limited | Novel method of treatment using a high dosage regimen of amoxycillin and potassium clavulanate |
US8889187B2 (en) * | 2000-02-24 | 2014-11-18 | Shionogi Inc. | Once a day amoxicillin product comprising immediate and delayed release dosage forms |
US7838032B2 (en) | 2000-04-28 | 2010-11-23 | Reckitt Benckiser Inc. | Sustained release of guaifenesin |
US7985421B2 (en) | 2000-04-28 | 2011-07-26 | Reckitt Benckiser Inc. | Sustained release formulations of guaifenesin and additional drug ingredients |
US8012504B2 (en) | 2000-04-28 | 2011-09-06 | Reckitt Benckiser Inc. | Sustained release of guaifenesin combination drugs |
US7985420B2 (en) | 2000-04-28 | 2011-07-26 | Reckitt Benckiser Inc. | Sustained release of guaifenesin combination drugs |
US6756057B2 (en) | 2000-10-12 | 2004-06-29 | Beecham Pharmaceuticals (Pte) Limited | Amoxicillin and potassium clavulanate dosage form |
US7011849B2 (en) | 2000-10-12 | 2006-03-14 | Beecham Pharmaceuticals (Pte) Limited | Second release phase formulation |
WO2005030179A1 (en) * | 2003-09-29 | 2005-04-07 | Cj Corporation | Sustained-release formulations |
WO2007059916A3 (en) * | 2005-11-23 | 2008-01-10 | Sandoz Ag | Pharmaceutical composition |
WO2007059916A2 (en) * | 2005-11-23 | 2007-05-31 | Sandoz Ag | Pharmaceutical composition |
US9801827B2 (en) | 2006-03-06 | 2017-10-31 | Pozen Inc. | Dosage forms for administering combinations of drugs |
WO2013057569A3 (en) * | 2011-10-19 | 2013-07-04 | Micro Labs Limited | Extended release pharmaceutical composition containing amoxicillin and clavulanic acid |
US11278506B2 (en) | 2015-10-09 | 2022-03-22 | Rb Health (Us) Llc | Pharmaceutical formulation |
US11020402B2 (en) | 2018-10-15 | 2021-06-01 | Axsome Therapeutics, Inc. | Use of reboxetine to treat narcolepsy |
US11135226B2 (en) | 2018-10-15 | 2021-10-05 | Axsome Therapeutics, Inc. | Use of reboxetine to treat narcolepsy |
US11185547B2 (en) | 2018-10-15 | 2021-11-30 | Axsome Therapeutics, Inc. | Use of reboxetine to treat narcolepsy |
US11351175B2 (en) | 2018-10-15 | 2022-06-07 | Axsome Therapeutics, Inc. | Use of reboxetine to treat narcolepsy |
US11364245B2 (en) | 2018-10-15 | 2022-06-21 | Axsome Therapeutics, Inc. | Use of reboxetine to treat narcolepsy |
Also Published As
Publication number | Publication date |
---|---|
US20020086056A1 (en) | 2002-07-04 |
US6838094B2 (en) | 2005-01-04 |
EP0752850B1 (en) | 2002-01-23 |
US6358528B1 (en) | 2002-03-19 |
US6136345A (en) | 2000-10-24 |
DE69525148D1 (en) | 2002-03-14 |
DE69525148T2 (en) | 2002-09-05 |
JPH09511994A (en) | 1997-12-02 |
EP0752850A1 (en) | 1997-01-15 |
GB9407386D0 (en) | 1994-06-08 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP0752850B1 (en) | Pharmaceutical formulation | |
US5910322A (en) | Delayed release pharmaceutical formulation containing amoxycillin and potassium clavulanate | |
US8303988B2 (en) | Antifungal once-a-day product, use and formulation thereof | |
US4798724A (en) | Solid, stable dosage forms with an elastic film coating | |
EP1867326B1 (en) | Enteric coated granule and method for preparing the same | |
EP0742712A1 (en) | Bilayered amoxycillin tablets | |
US20010001658A1 (en) | Granule modulating hydrogel system | |
US20070134327A1 (en) | Compositions and methods for improved efficacy of penicillin-type antibiotics | |
US8299052B2 (en) | Pharmaceutical compositions and methods for improved bacterial eradication | |
WO1996004907A1 (en) | Pharmaceutical formulation | |
CA2533178C (en) | Antibiotic product, use and formulation thereof | |
EP0377439B1 (en) | Controlled-release, low-dose aspirin | |
CA2535398C (en) | Antibiotic product, use and formulation thereof | |
JP2003518488A (en) | Pharmaceutical formulation containing sodium amoxicillin and potassium clavulanate | |
US20040228918A1 (en) | Granule modulating hydrogel system | |
EP1663169A1 (en) | Antibiotic product, use and formulation thereof | |
EP1658034A2 (en) | Antibiotic product, use and formulation thereof | |
EP1968586A2 (en) | Pharmaceutical compositions and methods for improved bacterial eradication |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): JP US |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE |
|
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: 1995915856 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 08718550 Country of ref document: US |
|
WWP | Wipo information: published in national office |
Ref document number: 1995915856 Country of ref document: EP |
|
WWG | Wipo information: grant in national office |
Ref document number: 1995915856 Country of ref document: EP |