EP1333807A2 - Derives d'erythromycine a liberation prolongee - Google Patents

Derives d'erythromycine a liberation prolongee

Info

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Withdrawn
Application number
EP01986972A
Other languages
German (de)
English (en)
Other versions
EP1333807A4 (fr
Inventor
Sandra E. Wassink
Donald J. Treacy, Jr.
Edward M. Rudnic
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
MiddleBrook Pharmaceuticals Inc
Original Assignee
Advancis Pharmaceutical Corp
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 Pharmaceutical Corp filed Critical Advancis Pharmaceutical Corp
Publication of EP1333807A2 publication Critical patent/EP1333807A2/fr
Publication of EP1333807A4 publication Critical patent/EP1333807A4/fr
Withdrawn legal-status Critical Current

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

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Oncology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Communicable Diseases (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (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.
EP01986972A 2000-10-13 2001-10-12 Derives d'erythromycine a liberation prolongee Withdrawn EP1333807A4 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US689988 1991-04-23
US68998800A 2000-10-13 2000-10-13
PCT/US2001/032055 WO2002038577A2 (fr) 2000-10-13 2001-10-12 Derives d'erythromycine a liberation prolongee

Publications (2)

Publication Number Publication Date
EP1333807A2 true EP1333807A2 (fr) 2003-08-13
EP1333807A4 EP1333807A4 (fr) 2005-06-29

Family

ID=24770642

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01986972A Withdrawn EP1333807A4 (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)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
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
CA2535398C (fr) 2003-08-12 2013-11-12 Advancis Pharmaceuticals Corporation Antibiotique, utilisation et formulation associees
CN102429882B (zh) * 2004-11-04 2015-03-25 什诺波特有限公司 加巴喷丁前体药物持续释放口服剂型

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991019486A1 (fr) * 1990-06-14 1991-12-26 Kalmo Enterprises, Inc. Suspensions de medicaments aqueuses stables
US5707646A (en) * 1992-03-12 1998-01-13 Taisho Pharmaceutical Co., Ltd. Taste masking pharmaceutical composition
EP0826376A1 (fr) * 1995-05-02 1998-03-04 Taisho Pharmaceutical Co. Ltd Composition s'administrant par voie orale
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 (fr) * 1999-03-17 2000-09-21 Daiichi Pharmaceutical Co., Ltd. Compositions medicamenteuses
WO2000069415A2 (fr) * 1999-05-19 2000-11-23 LEK, tovarna farmacevtskih in kemičnih izdelkov, d.d. Granulation par fusion

Family Cites Families (7)

* 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
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
US6010718A (en) * 1997-04-11 2000-01-04 Abbott Laboratories Extended release formulations of erythromycin derivatives
JP2000169364A (ja) * 1998-09-30 2000-06-20 Taisho Pharmaceut Co Ltd 経口製剤用粒子

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991019486A1 (fr) * 1990-06-14 1991-12-26 Kalmo Enterprises, Inc. Suspensions de medicaments aqueuses stables
US5707646A (en) * 1992-03-12 1998-01-13 Taisho Pharmaceutical Co., Ltd. Taste masking pharmaceutical composition
EP0826376A1 (fr) * 1995-05-02 1998-03-04 Taisho Pharmaceutical Co. Ltd Composition s'administrant par voie orale
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 (fr) * 1999-03-17 2000-09-21 Daiichi Pharmaceutical Co., Ltd. Compositions medicamenteuses
WO2000069415A2 (fr) * 1999-05-19 2000-11-23 LEK, tovarna farmacevtskih in kemičnih izdelkov, d.d. Granulation par fusion

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO0238577A2 *

Also Published As

Publication number Publication date
WO2002038577A3 (fr) 2002-09-19
JP2004528272A (ja) 2004-09-16
MXPA03003146A (es) 2004-12-06
WO2002038577A2 (fr) 2002-05-16
CA2425688A1 (fr) 2002-05-16
EP1333807A4 (fr) 2005-06-29
AU2002239232A1 (en) 2002-05-21

Similar Documents

Publication Publication Date Title
US8633241B2 (en) Nebivolol and its pharmaceutically acceptable salts, process for preparation and pharmaceutical compositions of nebivolol
US4562069A (en) Two-phase formulation
EP1858514B1 (fr) Comprimes pharmaceutiques de forme cristalline d'aripiprazole ii
EP2041084B1 (fr) Co-cristaux de pyrrolidinones
AU775946B2 (en) Stable pharmaceutical formulation comprising a HMG-CoA reductase inhibitor
EP1901736B1 (fr) Composition pharmaceutique comprenant de la simvastatine et de l'ézétimibe
CN101528262A (zh) 药物组合物
RU2349306C2 (ru) Лекарственные средства, содержащие тригидрат гидрохлорида варденафила
KR20040010681A (ko) 신규한 약학 조성물
AU2000249434A1 (en) Stabilized pharmaceutically effective composition and pharmaceutical formulation comprising the same
JP2004501121A (ja) 安定した医薬効果を有する合成物、及びそれを含む医薬製剤
EP1080721B1 (fr) Dispersant solide noncristallin comprenant du céfuroxime axétil
CN107397732A (zh) 提高依折麦布片溶出度的方法
KR100988233B1 (ko) 클로피도그렐 1,5-나프탈렌 다이술폰산 염 또는 이의수화물의 약학 조성물 및 제제
WO2002038577A2 (fr) Derives d'erythromycine a liberation prolongee
EP1296672B1 (fr) Produit et preparation pharmaceutiques stables
JP2001527047A (ja) 超水和シチコリン、プロセスおよび使用
KR20000018902A (ko) 생체이용률이 증가된 이트라코나졸 함유 항진균용 조성물
AU3940999A (en) Novel formulation containing paroxetine
CN117695279A (zh) 氯雷他定组合物及氯雷他定药物
CN102805745A (zh) 一种伊潘立酮组合物及其制备方法
MXPA00011154A (en) Novel formulation containing paroxetine

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