US20080113020A1 - Solid pharmaceutical composition comprising telithromycin - Google Patents

Solid pharmaceutical composition comprising telithromycin Download PDF

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Publication number
US20080113020A1
US20080113020A1 US11/839,719 US83971907A US2008113020A1 US 20080113020 A1 US20080113020 A1 US 20080113020A1 US 83971907 A US83971907 A US 83971907A US 2008113020 A1 US2008113020 A1 US 2008113020A1
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Prior art keywords
weight
telithromycin
composition
povidone
tablets
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Abandoned
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US11/839,719
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English (en)
Inventor
Christian Desesquelle
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.)
Sanofi Aventis France
Aventis Pharma SA
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Sanofi Aventis France
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Application filed by Sanofi Aventis France filed Critical Sanofi Aventis France
Assigned to AVENTIS PHARMA S.A.. reassignment AVENTIS PHARMA S.A.. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: DESESQUELLE, CHRISTIAN
Publication of US20080113020A1 publication Critical patent/US20080113020A1/en
Priority to US14/014,677 priority Critical patent/US8962021B2/en
Assigned to AVENTIS PHARMA S.A. reassignment AVENTIS PHARMA S.A. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: DESESQUELLE, CHRISTIAN
Abandoned legal-status Critical Current

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    • 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
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
    • A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
    • 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
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
    • 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
    • A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
    • A61K9/2806—Coating materials
    • A61K9/2833—Organic macromolecular compounds
    • A61K9/286—Polysaccharides, e.g. gums; Cyclodextrin
    • A61K9/2866—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
    • 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
    • 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 novel solid pharmaceutical composition of telithromycin that in particular allows facilitated swallowing by the patient.
  • the unit amount of active ingredient to be administered orally via a solid pharmaceutical composition often makes it necessary to prepare tablets that are of a size such that the swallowing thereof can give many patients, children of course, but not only children, difficulties.
  • the nature of the active ingredient makes it necessary to add thereto a certain number of excipients that are sometimes themselves in considerable amount in order to ensure the cohesion of the formulation, but also to perform an important, or even essential, function, for example when masking of the taste of the active ingredient is desired. This is most particularly the case for compounds of macrolide/ketolide type, such as telithromycin.
  • FIG. 1 is a graph that shows tablet hardness vs. compression force for tablets prepared in accordance with Example 1.
  • telithromycin or 11,12-dideoxy-3-de((2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl)oxy)-6-O-methyl-3-oxo-12,11-(oxycarbonyl-((4-(4-(3-pyridinyl)- 1 H-imidazol-1-yl)butylimino))erythromycin, is described in European Patent EP 0 680 967. Oral administration is a favoured administration form for this active ingredient having antibiotic properties.
  • Telithromycin tablets containing a dose of 400 mg and 300 mg are thus currently sold. These tablets contain a proportion of active ingredient of 50% by weight, relative to the total weight of the tablet before coating, and also a considerable proportion of excipient for granulation (close to 30% by weight of lactose), a mixture of excipients for disintegration (close to 13% by weight of a mixture of corn starch in a very high proportion and of sodium croscarmellose in a very low proportion), a low percentage of diluent (between 4 and 5% by weight of microcrystalline cellulose), and a low percentage of binder (less than 2% by weight) and of lubricant (less than 1% by weight), these tablets being coated with a film-coating.
  • excipient for granulation close to 30% by weight of lactose
  • a mixture of excipients for disintegration close to 13% by weight of a mixture of corn starch in a very high proportion and of sodium croscarmellose in a very low
  • These tablets containing 400 mg and 300 mg of telithromycin thus have a total mass, respectively, of 800 and 600 mg (not including the film-coating) and have an oblong shape with large dimensions, respectively of (18 mm ⁇ 9 mm) and (13.9 mm ⁇ 8.7 mm). It can therefore readily be seen that the swallowing of such tablets by patients is sometimes difficult.
  • telithromycin active ingredient has specific mechanical properties such that this is not possible for the tablets currently sold: the proportion of 50% by weight of telithromycin in the compositions before coating for the tablets sold, as indicated above, constitutes a maximum.
  • Telithromycin is in fact an active ingredient which is difficult to compress. The result is that the mechanical characteristics of the tablets obtained are not satisfactory, especially for allowing high-throughput production. During the compression process, a tendency for the tablets to split can appear, which results in a high rejection rate of tablets declared to be non-conform due to a defect in appearance related to a lack of cohesion and, consequently, a notable economic loss.
  • telithromycin tablets have now been found, entirely surprisingly and unexpectedly, by virtue of which it is possible to simultaneously remedy the major drawbacks mentioned above, in particular, firstly, to be able to include a much higher proportion of the telithromycin active ingredient, ranging up to 80% by weight of the tablet excluding film-coating and, consequently, at an equal dosage of active principle, to provide tablets whose size is very substantially reduced and, secondly, to be able to quite significantly increase the breaking strength of the tablet before coating and, consequently, to very substantially reduce, on the industrial scale, the rejection rate of tablets for a defect in appearance related to a lack of cohesion.
  • a subject of the present invention is thus a solid pharmaceutical composition comprising telithromycin or an addition salt thereof with a pharmaceutically acceptable acid, as an active ingredient, characterized in that it comprises, relative to the total weight of the composition:
  • the proportions indicated by weight relative to the total weight of the composition are understood to mean relative to the total weight of the composition without taking into account any possible coating of the latter, in particular with a film-coating.
  • the proportions by weight indicated for the telithromycin active ingredient, whether or not it is present in the form of an addition salt thereof with a pharmaceutically acceptable acid are proportions calculated by weight of the telithromycin compound relative to the total weight of the composition without taking into account any possible coating of the latter, in particular with a film-coating.
  • addition salt of telithromycin with a pharmaceutically acceptable acid mention may in particular be made of addition salts with inorganic or organic acids, especially the salts formed with acetic acid, propionic acid, trifluoroacetic acid, maleic acid, tartaric acid, methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid or phosphoric acid, and more particularly stearic acid, ethylsuccinic acid or laurylsulfuric acid.
  • the composition according to the invention preferably comprises telithromycin, or an addition salt thereof with a pharmaceutically acceptable acid, in a proportion of telithromycin of between 50 and 80% by weight, more particularly between 60 and 80% by weight, and even more particularly between 60 and 70% by weight, relative to the total weight of the composition.
  • the present invention it has in particular been noted, surprisingly, that, by very substantially increasing the proportion of one of the excipients in the composition already sold for telithromycin tablets, indicated above, to the detriment of two other specific excipients of this same already known composition, it is possible both to increase the proportion of the telithromycin active ingredient, up to at least 80% by weight, while at the same time improving the breaking strength of the tablets, in particular during the composition compression process.
  • this specific excipient i.e. the diluent, in particular microcrystalline cellulose
  • diotin having a plastic behaviour is thus intended to mean, according to the invention, any excipient known to those skilled in the art that exhibits both this function of diluent and, at a proportion by weight of between 10 and 50% by weight, this plasticizing function with respect to the telithromycin composition, in particular during the compression thereof. p It has, moreover, been possible to note that this result, which is as advantageous as it is unexpected, is further improved by acting on the other excipients also present in the composition of the tablets sold.
  • the pharmaceutical composition according to the invention also comprises, relative to the total weight of the composition:
  • the diluent having a plastic behaviour is present in a proportion of between 20 and 30% by weight, relative to the total weight of the composition according to the invention.
  • composition according to the present invention is characterized in that it comprises, relative to the total weight of the composition:
  • the diluent having a plastic behaviour as defined above is microcrystalline cellulose.
  • the pharmaceutical composition according to the invention is characterized in that:
  • composition according to the invention is characterized in that:
  • the pharmaceutical composition according to the invention is characterized in that it comprises, relative to the total weight of the composition:
  • the solid composition according to the invention can, of course, consist of the composition intended to be subjected to the compression process, i.e. the composition resulting from this process.
  • the pharmaceutical composition according to the invention is characterized in that it is in the form of a tablet.
  • the telithromycin can in particular be present in the composition according to the invention in the form of granulated material obtained by granulation, in particular by wet granulation, the pharmaceutical composition according to the invention thus comprising telithromycin granulated material dispersed in an external phase comprising other components of the composition, before or after the compression process.
  • the telithromycin granulated material also comprises said binder and the external phase comprises said disintegrating agent and lubricant. It has been possible to observe that the diluent having a plastic behaviour can be present in said telithromycin granulated material and said external phase.
  • the tablet which results therefrom can also be subjected in particular to a coating operation, in particular with a film-coating according to operating conditions well known to those skilled in the art.
  • the pharmaceutical composition according to the invention is characterized in that it is in the form of a tablet and in that it is coated with a film-coating.
  • this film-coating can comprise at least one component chosen from the group consisting of hypromellose, polyethylene glycol, titanium dioxide, talc, yellow iron oxide and red iron oxide, and mixtures thereof.
  • the pharmaceutical composition according to the invention preferably comprises from 50 mg to 600 mg of telithromycin, in particular 400 mg or alternatively 300 mg of telithromycin.
  • the novel composition according to the invention thus makes it possible, for dosages of telithromycin active ingredient of 400 and 300 mg, i.e. identical to that of the existing tablets, to have reduced dimensions.
  • the tablets according to the invention have sizes which are, respectively, (13.9 mm ⁇ 8.7 mm) and (12.5 mm ⁇ 7.8 mm).
  • the composition according to the invention can therefore advantageously have a reduced size, in the form of a tablet, at a telithromycin dosage that is nevertheless equal, compared to the tablets of the composition sold, which in itself provides a very important advantage both in terms of patient adherence and in terms of reduction of the production costs of the finished pharmaceutical product.
  • these reduced-size tablets exhibit better hardness, which, on the industrial scale, is reflected by a very advantageous decrease in the rejection rate of tablets for a defect in appearance related to a lack of cohesion, for example from 2% to 0.02% for 300 mg telithromycin tablets.
  • FIG. 1 represents three dashed curves showing the hardness (in N) of three tablets as a function of the compression force (in kN) according to the breaking strength test described hereinafter.
  • the curve with the smallest dashes corresponds to the test on the composition according to the invention prepared in Example 1.1 (before compression and film-coating), the curve with the largest dashes corresponds to the test on the composition of the tablets sold (before compression and film-coating), and the curve with intermediate-sized dashes corresponds to the test on the powder of telithromycin active ingredient.
  • Telithromycin-based tablets the composition of which is reported in the following Table 1 (composition according to the invention, coated with a film-coating), are prepared.
  • the wet granulated material thus obtained is broken up using a CoMil rotary calibrating device equipped with a screen having a 9.5 mm mesh size, and the broken up granulated material is then transferred into a drying tank. It is maintained therein at 60° C. in a fluidized air bed dryer until a residual salvation of less than 2% is obtained.
  • the dried granulated material is then sieved using a calibrating device equipped with a screen having a 1.6 mm mesh size.
  • the granulated material thus obtained is then compressed using a compression press having the equipment required for the desired dosage of 400 mg.
  • a film-coating solution is prepared as follows.
  • the suspension obtained is used to film-coat the tablets obtained above, in an Accela Cota film-coating pan.
  • telithromycin tablets Proportion Component (% by weight; with film-coating) Active ingredient telithromycin 65.20% (400 mg) Excipients microcrystalline cellulose 1 25.10% Sodium croscarmellose 2 3.91% povidone K25 3 2.93% magnesium stearate 0.65% Film-coating hypromellose 6 cP 4 1.62% polyethylene glycol 8000 5 0.07% titanium dioxide 0.34% talc 0.12% yellow iron oxide 0.05% red iron oxide 0.01% Total (with film-coating) 100.00% 1 Avicel PH 1001 sold by FMC 2 Ac-Di-Sol sold by FMC 3 Kollidon 25 sold by BASF 4 Pharmacoat 606 sold by Shin-Etsu 5 Polyglycol 8000P sold by Hoechst
  • the compressibility of a powder is evaluated by its ability to form a compact when it is subjected to a pressure. This is carried out in the context of the method illustrated above, using an alternating compression press equipped with punches bearing strain gauges. An amplification system and a converter make it possible to register, at any moment, the forces applied during the compression cycle. At the end of the process, the breaking strength of the tablet formed is measured by means of a hardness bench. A measurement of breaking strength or “hardness” of the tablet (in N) is thus obtained for a given compression force (in kN). For a powder to be tested, this process is repeated several times so as to be able to plot a curve such as those of FIG. 1 .

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  • Health & Medical Sciences (AREA)
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  • Animal Behavior & Ethology (AREA)
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  • Communicable Diseases (AREA)
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US11/839,719 2005-02-25 2007-08-16 Solid pharmaceutical composition comprising telithromycin Abandoned US20080113020A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US14/014,677 US8962021B2 (en) 2005-02-25 2013-08-30 Solid pharmaceutical composition comprising telithromycin

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0501936A FR2882522B1 (fr) 2005-02-25 2005-02-25 Composition pharmaceutique solide comprenant de la telithromycine
FR0501936 2005-02-25
PCT/FR2006/000411 WO2006090067A1 (fr) 2005-02-25 2006-02-23 Composition pharmaceutique solide comprenant de la telithromycine

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PCT/FR2006/000411 Continuation WO2006090067A1 (fr) 2005-02-25 2006-02-23 Composition pharmaceutique solide comprenant de la telithromycine

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US14/014,677 Continuation US8962021B2 (en) 2005-02-25 2013-08-30 Solid pharmaceutical composition comprising telithromycin

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US14/014,677 Expired - Fee Related US8962021B2 (en) 2005-02-25 2013-08-30 Solid pharmaceutical composition comprising telithromycin

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US (2) US20080113020A1 (de)
EP (1) EP1855695B1 (de)
JP (1) JP5063368B2 (de)
KR (1) KR101346453B1 (de)
CN (1) CN101180064B (de)
AR (1) AR053144A1 (de)
AT (1) ATE486633T1 (de)
AU (1) AU2006217814B2 (de)
BR (1) BRPI0608395A2 (de)
CA (1) CA2598210A1 (de)
CY (1) CY1111129T1 (de)
DE (1) DE602006017975D1 (de)
DK (1) DK1855695T3 (de)
ES (1) ES2354906T3 (de)
FR (1) FR2882522B1 (de)
HK (1) HK1120412A1 (de)
HR (1) HRP20110089T1 (de)
IL (1) IL185251A (de)
ME (1) ME01936B (de)
MX (1) MX2007010405A (de)
MY (1) MY145394A (de)
PL (1) PL1855695T3 (de)
PT (1) PT1855695E (de)
RS (1) RS51578B (de)
RU (1) RU2371184C2 (de)
SI (1) SI1855695T1 (de)
TW (1) TWI371280B (de)
UY (1) UY29403A1 (de)
WO (1) WO2006090067A1 (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20180028548A1 (en) * 2016-01-12 2018-02-01 Wockhardt Limited Pharmaceutical compositions

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2882522B1 (fr) 2005-02-25 2007-04-13 Aventis Pharma Sa Composition pharmaceutique solide comprenant de la telithromycine
CN102499936B (zh) * 2011-12-01 2013-06-26 西北农林科技大学 一种复方泰利霉素纳米乳口服液及其制备方法
JP6112696B1 (ja) * 2015-10-05 2017-04-12 富山化学工業株式会社 ソリスロマイシンを含む錠剤
WO2020021574A1 (en) * 2018-07-27 2020-01-30 Wockhardt Limited Pharmaceutical compositions and methods

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US20040013737A1 (en) * 2002-07-19 2004-01-22 Philippe Becourt Taste masked oral composition of telithromycin
US20040018737A1 (en) * 2002-07-12 2004-01-29 Kwak Noh Yeal Method of manufacturing semiconductor devices
US20040091536A1 (en) * 2001-03-09 2004-05-13 Julien Meisonnier Telithromycin suspension with masked taste
US20040228915A1 (en) * 2003-04-04 2004-11-18 Noack Robert M. Oral extended release compressed tablets of multiparticulates
US20050037983A1 (en) * 2003-03-11 2005-02-17 Timothy Dinan Compositions and methods for the treatment of depression and other affective disorders
US20060099266A1 (en) * 2002-12-23 2006-05-11 Rohra Rakhi H Slow release formulation of clarithromycin

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FR2719587B1 (fr) 1994-05-03 1996-07-12 Roussel Uclaf Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments.
AR024353A1 (es) * 1999-06-15 2002-10-02 He Chunhong Audifono y equipo auxiliar interactivo con relacion de voz a audio remanente
FR2826274B1 (fr) * 2001-06-21 2003-09-26 Aventis Pharma Sa Formulation pharmaceutique au gout masque et son procede de preparation
WO2004009059A1 (en) * 2002-07-19 2004-01-29 Aventis Pharma S.A. Taste masked oral composition of telithromycin
AU2003274927A1 (en) * 2002-08-23 2004-03-11 Genome Therapeutics Corporation Methods and reagents for preventing bacteremias
ATE448775T1 (de) * 2002-08-29 2009-12-15 Activbiotics Pharma Llc Rifalazil zur behandlung von infektionen mit clostridium difficile
FR2882522B1 (fr) 2005-02-25 2007-04-13 Aventis Pharma Sa Composition pharmaceutique solide comprenant de la telithromycine

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US20040091536A1 (en) * 2001-03-09 2004-05-13 Julien Meisonnier Telithromycin suspension with masked taste
US20040018737A1 (en) * 2002-07-12 2004-01-29 Kwak Noh Yeal Method of manufacturing semiconductor devices
US20040013737A1 (en) * 2002-07-19 2004-01-22 Philippe Becourt Taste masked oral composition of telithromycin
US20060099266A1 (en) * 2002-12-23 2006-05-11 Rohra Rakhi H Slow release formulation of clarithromycin
US20050037983A1 (en) * 2003-03-11 2005-02-17 Timothy Dinan Compositions and methods for the treatment of depression and other affective disorders
US20040228915A1 (en) * 2003-04-04 2004-11-18 Noack Robert M. Oral extended release compressed tablets of multiparticulates

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Handbook of Pharm. Excip. (1988); pg. 53 (microcrystalline cellulose) *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20180028548A1 (en) * 2016-01-12 2018-02-01 Wockhardt Limited Pharmaceutical compositions
US10857171B2 (en) * 2016-01-12 2020-12-08 Wockhardt Limited Pharmaceutical compositions

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KR20070106581A (ko) 2007-11-01
KR101346453B1 (ko) 2014-01-02
ME01936B (en) 2016-10-19
HK1120412A1 (en) 2009-04-03
EP1855695B1 (de) 2010-11-03
DE602006017975D1 (de) 2010-12-16
RU2371184C2 (ru) 2009-10-27
HRP20110089T1 (hr) 2011-03-31
AU2006217814A1 (en) 2006-08-31
FR2882522A1 (fr) 2006-09-01
CN101180064A (zh) 2008-05-14
RU2007135367A (ru) 2009-03-27
IL185251A (en) 2012-10-31
AU2006217814B2 (en) 2011-08-11
PT1855695E (pt) 2011-01-19
BRPI0608395A2 (pt) 2009-12-29
CY1111129T1 (el) 2015-06-11
ES2354906T3 (es) 2011-03-21
DK1855695T3 (da) 2011-02-21
MX2007010405A (es) 2007-10-17
PL1855695T3 (pl) 2011-04-29
ATE486633T1 (de) 2010-11-15
FR2882522B1 (fr) 2007-04-13
MY145394A (en) 2012-02-15
RS51578B (en) 2011-08-31
WO2006090067A1 (fr) 2006-08-31
EP1855695A1 (de) 2007-11-21
AR053144A1 (es) 2007-04-25
IL185251A0 (en) 2008-02-09
UY29403A1 (es) 2006-10-02
SI1855695T1 (sl) 2011-02-28
JP5063368B2 (ja) 2012-10-31
TW200640472A (en) 2006-12-01
TWI371280B (en) 2012-09-01
CA2598210A1 (fr) 2006-08-31
US8962021B2 (en) 2015-02-24
CN101180064B (zh) 2010-09-22
US20130344151A1 (en) 2013-12-26
JP2008531529A (ja) 2008-08-14

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