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WO2002038577A2 - Derives d'erythromycine a liberation prolongee - Google Patents

Derives d'erythromycine a liberation prolongee Download PDF

Info

Publication number
WO2002038577A2
WO2002038577A2 PCT/US2001/032055 US0132055W WO0238577A2 WO 2002038577 A2 WO2002038577 A2 WO 2002038577A2 US 0132055 W US0132055 W US 0132055W WO 0238577 A2 WO0238577 A2 WO 0238577A2
Authority
WO
WIPO (PCT)
Prior art keywords
composition
long chain
host
treating
bacterial infection
Prior art date
Application number
PCT/US2001/032055
Other languages
English (en)
Other versions
WO2002038577A3 (fr
Inventor
Sandra E. Wassink
Donald J. Treacy, Jr.
Edward M. Rudnic
Original Assignee
Advancis Pharmaceuticals
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Advancis Pharmaceuticals filed Critical Advancis Pharmaceuticals
Priority to JP2002541109A priority Critical patent/JP2004528272A/ja
Priority to AU2002239232A priority patent/AU2002239232A1/en
Priority to EP01986972A priority patent/EP1333807A4/fr
Priority to CA002425688A priority patent/CA2425688A1/fr
Publication of WO2002038577A2 publication Critical patent/WO2002038577A2/fr
Publication of WO2002038577A3 publication Critical patent/WO2002038577A3/fr

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

La présente invention concerne une composition pharmaceutique constituée d'un dérivé d'érythromycine et d'un matériau non polymère assurant la libération prolongée, plus particulièrement un élément sélectionné dans le groupe formé par les argiles, les hydrocarbures à longue chaîne, les acides carboxyliques à longue chaîne, les esters d'acide carboxylique à longue chaîne, les alcools à longue chaîne et les mélanges de ces derniers; ledit élément étant présent suivant une quantité suffisante pour assurer la libération prolongée du dérivé d'érythromycine.
PCT/US2001/032055 2000-10-13 2001-10-12 Derives d'erythromycine a liberation prolongee WO2002038577A2 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP2002541109A JP2004528272A (ja) 2000-10-13 2001-10-12 持続型放出エリスロマイシン誘導体
AU2002239232A AU2002239232A1 (en) 2000-10-13 2001-10-12 Extended release erythromycin derivatives
EP01986972A EP1333807A4 (fr) 2000-10-13 2001-10-12 Derives d'erythromycine a liberation prolongee
CA002425688A CA2425688A1 (fr) 2000-10-13 2001-10-12 Derives d'erythromycine a liberation prolongee

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US68998800A 2000-10-13 2000-10-13
US06/689,988 2000-10-13

Publications (2)

Publication Number Publication Date
WO2002038577A2 true WO2002038577A2 (fr) 2002-05-16
WO2002038577A3 WO2002038577A3 (fr) 2002-09-19

Family

ID=24770642

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2001/032055 WO2002038577A2 (fr) 2000-10-13 2001-10-12 Derives d'erythromycine a liberation prolongee

Country Status (6)

Country Link
EP (1) EP1333807A4 (fr)
JP (1) JP2004528272A (fr)
AU (1) AU2002239232A1 (fr)
CA (1) CA2425688A1 (fr)
MX (1) MXPA03003146A (fr)
WO (1) WO2002038577A2 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008518971A (ja) * 2004-11-04 2008-06-05 ゼノポート，インコーポレイティド ガバペンチンプロドラッグ持続放出経口薬剤
US8303988B2 (en) 2000-10-13 2012-11-06 Shionogi Inc. Antifungal once-a-day product, use and formulation thereof

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6565882B2 (en) 2000-02-24 2003-05-20 Advancis Pharmaceutical Corp Antibiotic composition with inhibitor
US6544555B2 (en) 2000-02-24 2003-04-08 Advancis Pharmaceutical Corp. Antibiotic product, use and formulation thereof
US6541014B2 (en) 2000-10-13 2003-04-01 Advancis Pharmaceutical Corp. Antiviral product, use and formulation thereof
EP1653924A4 (fr) 2003-08-12 2009-09-09 Middlebrook Pharmaceuticals In Antibiotique, utilisation et formulation associees

Family Cites Families (14)

* Cited by examiner, † Cited by third party
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 (fr) * 1973-02-03 1974-10-14
JP2528652B2 (ja) * 1987-03-30 1996-08-28 エスエス製薬株式会社 持効性セフラジン製剤
US4808411A (en) * 1987-06-05 1989-02-28 Abbott Laboratories Antibiotic-polymer compositions
CA2085342A1 (fr) * 1990-06-14 1991-12-15 Milton R. Kaplan Suspension aqueuse stable de medicament
JP3265680B2 (ja) * 1992-03-12 2002-03-11 大正製薬株式会社 経口製剤用組成物
JPH07267850A (ja) * 1994-03-28 1995-10-17 Eisai Co Ltd 不快味を防止した医薬組成物及びその製造方法
KR100404293B1 (ko) * 1995-05-02 2004-02-18 다이쇼 세이야꾸 가부시끼가이샤 경구투여용조성물
US5858986A (en) * 1996-07-29 1999-01-12 Abbott Laboratories Crystal form I of clarithromycin
US6010718A (en) * 1997-04-11 2000-01-04 Abbott Laboratories Extended release formulations of erythromycin derivatives
US5780604A (en) * 1997-09-26 1998-07-14 Abbott Laboratories 11,12-cyclic phosphite or phosphate derivatives of erythromycin and related macrolides
JP2000169364A (ja) * 1998-09-30 2000-06-20 Taisho Pharmaceut Co Ltd 経口製剤用粒子
EP1161956A4 (fr) * 1999-03-17 2005-03-16 Daiichi Seiyaku Co Compositions medicamenteuses
SI20244A (sl) * 1999-05-19 2000-12-31 LEK, tovarna farmacevtskih in kemi�nih izdelkov, d.d. Granulacija v talini

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8303988B2 (en) 2000-10-13 2012-11-06 Shionogi Inc. Antifungal once-a-day product, use and formulation thereof
JP2008518971A (ja) * 2004-11-04 2008-06-05 ゼノポート，インコーポレイティド ガバペンチンプロドラッグ持続放出経口薬剤
JP2013107900A (ja) * 2004-11-04 2013-06-06 Xenoport Inc ガバペンチンプロドラッグ持続放出経口薬剤
US8795725B2 (en) 2004-11-04 2014-08-05 Xenoport, Inc. GABA analog prodrug sustained release oral dosage forms
US8906412B2 (en) 2004-11-04 2014-12-09 Xenoport, Inc. GABA analog prodrug sustained release oral dosage forms

Also Published As

Publication number Publication date
AU2002239232A1 (en) 2002-05-21
CA2425688A1 (fr) 2002-05-16
JP2004528272A (ja) 2004-09-16
MXPA03003146A (es) 2004-12-06
WO2002038577A3 (fr) 2002-09-19
EP1333807A2 (fr) 2003-08-13
EP1333807A4 (fr) 2005-06-29

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