EP1333807A2 - Extended release erythromycin derivatives - Google Patents
Extended release erythromycin derivativesInfo
- Publication number
- EP1333807A2 EP1333807A2 EP01986972A EP01986972A EP1333807A2 EP 1333807 A2 EP1333807 A2 EP 1333807A2 EP 01986972 A EP01986972 A EP 01986972A EP 01986972 A EP01986972 A EP 01986972A EP 1333807 A2 EP1333807 A2 EP 1333807A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- composition
- long chain
- host
- treating
- bacterial infection
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Definitions
- the invention relates to a pharmaceutical composition of erythromycin derivatives with an extended release profile.
- Erythromycin as well as derivatives thereof, have been used as an antibacterial agent, and are generally provided as an immediate release composition.
- U.S. Patent 6,010,718 discloses a pharmaceutical composition having extended release characteristics wherein erythromycin or a derivative thereof is employed in a pharmaceutical composition wherein the pharmaceutically acceptable carrier for the erythromycin or derivative thereof is a polymer, with such polymer generally being in an amount from about 5% to about 50% by weight of the composition.
- a pharmaceutical composition for extended release of an erythromycin derivative wherein such erythromycin derivative is combined with a non-polymer hydrophobic material.
- a non-polymer hydrophobic material provides for extended release of the erythromycin derivative and is preferably at least one of a clay, a long chain hydrocarbon, a long chain alcohol, a long chain ester or a long chain acid. More particularly, the extended release characteristics for the erythromycin derivative are provided by coating the erythromycin derivative with a clay, a long chain hydrocarbon, a long chain alcohol, a long chain ester, or a long chain acid.
- a long chain hydrocarbon is a hydrocarbon that contains at least 12 carbon atoms, and in general, such a hydrocarbon contains from about 12 to 22 carbon atoms.
- the hydrocarbon may be branched or unbranched, or may be saturated or unsaturated, and, when unsaturated, may contain one or more double bonds.
- a long chain carboxylic acid and/or long chain carboxylic acid ester and/or a long chain alcohol also preferably contains at least 12 carbon atoms, and more preferably, contains from 12 to 22 carbon atoms.
- such hydrocarbons are aliphatic hydrocarbons, and may be saturated or unsaturated and may be branched or unbranched. If unsaturated, the hydrocarbon portion may contain one or more double bonds.
- such long chain alcohols, esters and acids may contain three carbon rings or hydroxyl groups.
- a long chain alcohol is represented by an aliphatic hydrocarbon alcohol that preferably contains at least 12 carbon atoms, and may contain one or more hydroxyl groups.
- long chain carboxylic acids there may be mentioned: n-dodecanoic acid, ⁇ -tetradecanoic acid, ⁇ -hexadecanoic acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, montanic acid and melissic acid.
- unsaturated monoolefinic straight chain monocarboxylic acids examples of these are oleic acid, gadoleic acid and erucic acid.
- unsaturated (polyolefinic) straight chain monocarboxyilic acid examples of these are linoleic acid, ricinoleic acid, linolenic acid, arachidonic acid and behenolic acid.
- Useful branched acids include, for example, diacetyl tartaric acid.
- glyceryl monostearates As representative examples of long chain carboxylic acid esters, there may be mentioned: glyceryl monostearates; glyceryl monopalmitates; mixtures of glyceryl monostearate and glyceryl monopalmitate (Myvaplex 600.
- glyceryl monolinoleate glyceryl monooleate; mixtures of glyceryl monopalmitate, glyceryl monostearate, glyceryl monooleate and glyceryl monolinoleate (Myverol 18-92, Eastman Fine Chemical Company); glyceryl onolinolenate; glyceryl monogadoleate; mixtures of glyceryl monopalmitate, glyceryl monostearate, glyceryl monooleate, glyceryl monolinoleate, glyceryl monolinolenate and glyceryl monogadoleate (Myverol 18-99, Eastman Fine Chemical Company); acetylated glycerides such as distilled acetylated monoglycerides (Myvacet 5-07, 7-07 and 9-45, Eastman Fine Chemical Company); mixtures of propylene glycol onoesters, distilled monoglycer
- clays there may be mentioned: Kaolin, Bentonite, magnesium aluminum silicate, magnesium trisilicate, talc, or calcium silicate.
- the erythromycin derivative is coated with a material as hereinabove described to provide for sustained release of the erythromycin derivative.
- the extended released material is generally employed in an amount of from about 1% to about 60%, by weight of the composition, and preferably from about 5% to about 50% of the composition.
- composition may further include pharmaceutically acceptable excipients and/or fillers and extenders such as lactose, starches, dicalcium phosphate, calcium sulfate, calcium carbonate, glucose, sucrose, mannitol and silicic acid, lubricants such as talc, calcium stearate, magnesium stearate, etc.
- excipients and/or fillers and extenders such as lactose, starches, dicalcium phosphate, calcium sulfate, calcium carbonate, glucose, sucrose, mannitol and silicic acid, lubricants such as talc, calcium stearate, magnesium stearate, etc.
- extended release properties are achieved in accordance with the invention by using the extended release agents as hereinabove described, whereby it is not necessary to add a polymer to the composition, it is possible to include a polymer in the composition for other purposes.
- a polymer is present in the composition, such polymer is present in an amount of less than 5% by weight, generally in an amount less than 2% by weight, and more preferably in an amount less than 1% by weight. In most cases, the composition is free of a polymer in that a polymer is not required to achieve extended release properties.
- composition is preferably used as an oral dosage form; for example, in the form of a tablet or capsule.
- the oral dosage form of the present invention which provides for extended release of an erythromycin derivative may also be employed in a liquid oral dosage form, which may include an emulsion, a micro-emulsion, a suspension, syrup, etc.
- the pharmaceutical composition of the present invention includes an erythromycin derivative in an amount from about 45% to about 60% by weight, and preferably contains about 50% by weight of the erythromycin derivative.
- the erythromycin derivative is preferably 6-0-methoxy erythromycin A, known as Clarithromycin.
- composition of the invention is administered to a host in an amount effective to treat a bacterial infection.
- a daily dose of the composition of the invention is preferably delivered in a single dose and can range from about 500 mg to 1000 mg per day, with the pharmaceutical generally being administered for periods of from 5 to 14 days.
- a pharmaceutical composition in accordance with the invention can induce a statistically significantly lower mean fluctuation index in the plasma than ah immediate release composition while maintaining a similar bio-availability, or providing for increased bio-availability.
- Method A Melt the glyceryl monostearate and add the clarithromycin. Let cool and then mill through a screen. Blend the mixture with the lactose in a tumble blender for about 20 minutes. Add magnesium stearate and blend for 5 minutes. Compress the blend using a rotary tablet press.
- Method B Granulate lactose, glyceryl monostearate and clarithromycin together using a high shear granulator. Stop granulating when the gylceryl monosterate has completely melted. Screen the granulate. Blend the granulate and magnesium stearate for 5 minutes in a tumble blender. Compress the blend using a rotary tablet press.
- Method A Melt the ATMUL 84S and add the clarithromycin. Let cool and then mill through a screen. Blend the mixture with the lactose in a tumble blender for about 20 minutes. Add magnesium stearate and blend for 5 minutes. Compress the blend using a rotary tablet press.
- Method A Granulate lactose, cetyl alcohol and clarithromycin together using a high shear granulator. Stop granulating when the cetyl alcohol has completely melted. Screen the granulate. Blend the granulate and magnesium stearate for 5 minutes in a tumble blender. Compress the blend using a rotary tablet press.
- Method B Dissolve the cetyl alcohol in ethanol (95%). Granulate the clarithromycin and lactose with the cetyl alcohol solution. Screen the granulate and then dry. Blend the dried granulate and stearic acid in a tumble blend for 5 minutes. Compress the blend using a rotary tablet press.
- Example 8 Clarithromycin 50 Dextrose 34 Kaolin 15 Magnesium Stearate 1
- compositions of Examples 4-8 are formulated in a manner similar to the previous examples.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Communicable Diseases (AREA)
- Medicinal Chemistry (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US68998800A | 2000-10-13 | 2000-10-13 | |
US689988 | 2000-10-13 | ||
PCT/US2001/032055 WO2002038577A2 (en) | 2000-10-13 | 2001-10-12 | Extended release erythromycin derivatives |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1333807A2 true EP1333807A2 (en) | 2003-08-13 |
EP1333807A4 EP1333807A4 (en) | 2005-06-29 |
Family
ID=24770642
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP01986972A Withdrawn EP1333807A4 (en) | 2000-10-13 | 2001-10-12 | Extended release erythromycin derivatives |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP1333807A4 (en) |
JP (1) | JP2004528272A (en) |
AU (1) | AU2002239232A1 (en) |
CA (1) | CA2425688A1 (en) |
MX (1) | MXPA03003146A (en) |
WO (1) | WO2002038577A2 (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6544555B2 (en) | 2000-02-24 | 2003-04-08 | Advancis Pharmaceutical Corp. | Antibiotic product, use and formulation thereof |
US20020068078A1 (en) | 2000-10-13 | 2002-06-06 | Rudnic Edward M. | Antifungal product, use and formulation thereof |
AU2004264356B2 (en) | 2003-08-12 | 2011-01-27 | Shionogi, Inc. | Antibiotic product, use and formulation thereof |
CN101068538A (en) | 2004-11-04 | 2007-11-07 | 什诺波特有限公司 | Gaba analog prodrug sustained release oral dosage forms |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1991019486A1 (en) * | 1990-06-14 | 1991-12-26 | Kalmo Enterprises, Inc. | Stable aqueous drug suspensions |
US5707646A (en) * | 1992-03-12 | 1998-01-13 | Taisho Pharmaceutical Co., Ltd. | Taste masking pharmaceutical composition |
EP0826376A1 (en) * | 1995-05-02 | 1998-03-04 | Taisho Pharmaceutical Co. Ltd | Composition for oral administration |
US5780604A (en) * | 1997-09-26 | 1998-07-14 | Abbott Laboratories | 11,12-cyclic phosphite or phosphate derivatives of erythromycin and related macrolides |
US5858986A (en) * | 1996-07-29 | 1999-01-12 | Abbott Laboratories | Crystal form I of clarithromycin |
WO2000054811A1 (en) * | 1999-03-17 | 2000-09-21 | Daiichi Pharmaceutical Co., Ltd. | Medicinal compositions |
WO2000069415A2 (en) * | 1999-05-19 | 2000-11-23 | LEK, tovarna farmacevtskih in kemičnih izdelkov, d.d. | Melt granulation |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3108046A (en) * | 1960-11-25 | 1963-10-22 | Smith Kline French Lab | Method of preparing high dosage sustained release tablet and product of this method |
JPS49107855A (en) * | 1973-02-03 | 1974-10-14 | ||
JP2528652B2 (en) * | 1987-03-30 | 1996-08-28 | エスエス製薬株式会社 | Long-acting cefradine formulation |
US4808411A (en) * | 1987-06-05 | 1989-02-28 | Abbott Laboratories | Antibiotic-polymer compositions |
JPH07267850A (en) * | 1994-03-28 | 1995-10-17 | Eisai Co Ltd | Medicine composition prevented in unpleasant taste and method for producing the same |
US6010718A (en) * | 1997-04-11 | 2000-01-04 | Abbott Laboratories | Extended release formulations of erythromycin derivatives |
JP2000169364A (en) * | 1998-09-30 | 2000-06-20 | Taisho Pharmaceut Co Ltd | Granule for oral pharmaceutical preparation |
-
2001
- 2001-10-12 MX MXPA03003146A patent/MXPA03003146A/en unknown
- 2001-10-12 CA CA002425688A patent/CA2425688A1/en not_active Abandoned
- 2001-10-12 JP JP2002541109A patent/JP2004528272A/en active Pending
- 2001-10-12 AU AU2002239232A patent/AU2002239232A1/en not_active Abandoned
- 2001-10-12 EP EP01986972A patent/EP1333807A4/en not_active Withdrawn
- 2001-10-12 WO PCT/US2001/032055 patent/WO2002038577A2/en not_active Application Discontinuation
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1991019486A1 (en) * | 1990-06-14 | 1991-12-26 | Kalmo Enterprises, Inc. | Stable aqueous drug suspensions |
US5707646A (en) * | 1992-03-12 | 1998-01-13 | Taisho Pharmaceutical Co., Ltd. | Taste masking pharmaceutical composition |
EP0826376A1 (en) * | 1995-05-02 | 1998-03-04 | Taisho Pharmaceutical Co. Ltd | Composition for oral administration |
US5858986A (en) * | 1996-07-29 | 1999-01-12 | Abbott Laboratories | Crystal form I of clarithromycin |
US5780604A (en) * | 1997-09-26 | 1998-07-14 | Abbott Laboratories | 11,12-cyclic phosphite or phosphate derivatives of erythromycin and related macrolides |
WO2000054811A1 (en) * | 1999-03-17 | 2000-09-21 | Daiichi Pharmaceutical Co., Ltd. | Medicinal compositions |
WO2000069415A2 (en) * | 1999-05-19 | 2000-11-23 | LEK, tovarna farmacevtskih in kemičnih izdelkov, d.d. | Melt granulation |
Non-Patent Citations (1)
Title |
---|
See also references of WO0238577A2 * |
Also Published As
Publication number | Publication date |
---|---|
CA2425688A1 (en) | 2002-05-16 |
EP1333807A4 (en) | 2005-06-29 |
WO2002038577A3 (en) | 2002-09-19 |
MXPA03003146A (en) | 2004-12-06 |
WO2002038577A2 (en) | 2002-05-16 |
AU2002239232A1 (en) | 2002-05-21 |
JP2004528272A (en) | 2004-09-16 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
17P | Request for examination filed |
Effective date: 20030509 |
|
AK | Designated contracting states |
Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE TR |
|
AX | Request for extension of the european patent |
Extension state: AL LT LV MK RO SI |
|
RIN1 | Information on inventor provided before grant (corrected) |
Inventor name: RUDNIC, EDWARD, M. Inventor name: TREACY, DONALD, J., JR. Inventor name: WASSINK, SANDRA, E. |
|
A4 | Supplementary search report drawn up and despatched |
Effective date: 20050518 |
|
RIC1 | Information provided on ipc code assigned before grant |
Ipc: 7A 61K 31/7048 B Ipc: 7A 61K 47/14 B Ipc: 7A 61K 47/10 B Ipc: 7A 61K 47/02 B Ipc: 7A 61K 9/22 B Ipc: 7A 61K 9/20 A |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
18D | Application deemed to be withdrawn |
Effective date: 20050803 |