US20040029813A1 - Novel $g(beta crystalline form of perindopril tert-butylamine salt, preparation method, and pharmaceutical compositions containing same - Google Patents

Novel $g(beta crystalline form of perindopril tert-butylamine salt, preparation method, and pharmaceutical compositions containing same Download PDF

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Publication number
US20040029813A1
US20040029813A1 US10/312,902 US31290202A US2004029813A1 US 20040029813 A1 US20040029813 A1 US 20040029813A1 US 31290202 A US31290202 A US 31290202A US 2004029813 A1 US2004029813 A1 US 2004029813A1
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US
United States
Prior art keywords
compound
formula
crystalline form
preparation
pharmaceutical composition
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.)
Abandoned
Application number
US10/312,902
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English (en)
Inventor
Bruno Pfeiffer
Yves-Michel Ginot
Gerard Coquerel
Stephane Beilles
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.)
Laboratoires Servier SAS
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Laboratoires Servier SAS
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 Laboratoires Servier SAS filed Critical Laboratoires Servier SAS
Assigned to LES LABORATOIRES SERVIER reassignment LES LABORATOIRES SERVIER ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BEILLES, STEPHANE, COQUEREL, GERARD, GINOT, YVES-MICHEL, PFEIFFER, BRUNO
Publication of US20040029813A1 publication Critical patent/US20040029813A1/en
Priority to US11/052,489 priority Critical patent/US7259181B2/en
Abandoned legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/10—Antioedematous agents; Diuretics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives

Definitions

  • the present invention relates to a new ⁇ crystalline form of perindopril tert-butylamine salt of formula (I:
  • the present invention relates to the ⁇ crystalline form of the compound of formula (I), characterised by the following powder X-ray diffraction diagram, measured using a Siemens D5005 diffractometer (copper anticathode) and expressed in terms of inter-planar distance d, Bragg's angle 2 theta, intensity and relative intensity (expressed as a percentage of the most intense ray): Angle 2 theta Inter-planar Relative intensity (°) distance d ( ⁇ ) Intensity (%) 5.169 17.08 523 16.5 8.379 10.54 1001 31.5 9.350 9.45 3175 100 14.746 6.00 236 7.4 15.411 5.74 753 23.7 15.931 5.56 279 8.8 16.711 5.30 113 3.6 18.161 4.88 122 3.8 20.564 4.32 1198 37.7 21.285 4.17 330 10.4 21.781 4.08 317 10 22.632 3.93 190 6 23.308 3.81 133 4.2 23.797 3.74 427 13.
  • the invention relates also to a process for the preparation of the ⁇ crystalline form of the compound of formula (I), which process is characterised in that:
  • a solution of perindoprtil tert-butylamine salt in ethyl acetate is heated at reflux and is then rapidly cooled to 5° C. and the solid obtained is collected by filtration.
  • the concentration of the compound of formula (I) in the dichloromethane is preferably from 100 to 200 g/litre.
  • the concentration of the compound of formula (I) in the ethyl acetate is preferably from 70 to 90 g/litre.
  • the invention relates also to pharmaceutical compositions comprising as active ingredient the ⁇ crystalline form of the compound of formula (1) together with one or more appropriate, inert, non-toxic excipients.
  • pharmaceutical compositions according to the invention there may be mentioned more especially those that are suitable for oral, parenteral (intravenous or subcutaneous) or nasal administration, tablets or drages, sublingual tablets, gelatin capsules, lozenges, suppositories, creams, ointments, dermal gels, injectable preparations, drinkable suspensions etc.
  • the useful dosage can be varied according to the nature and severity of the disorder, the administration route and the age and weight of the patient. It varies from 1 to 500 mg per day in one or more administrations.
  • compositions according to the invention may also comprise a diuretic such as indapamide.
  • variable slits v6
  • Preparation formula for 1000 tablets each containing 4 mg of active ingredient Preparation formula for 1000 tablets each containing 4 mg of active ingredient: Compound of Example 1 4 g Hydroxypropylcellulose 2 g Wheat starch 10 g Lactose 100 g Magnesium stearate 3 g Talc 3 g

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Epidemiology (AREA)
  • Urology & Nephrology (AREA)
  • Hospice & Palliative Care (AREA)
  • Hematology (AREA)
  • Diabetes (AREA)
  • Vascular Medicine (AREA)
  • Peptides Or Proteins (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Indole Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
US10/312,902 2000-07-06 2001-07-06 Novel $g(beta crystalline form of perindopril tert-butylamine salt, preparation method, and pharmaceutical compositions containing same Abandoned US20040029813A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US11/052,489 US7259181B2 (en) 2000-07-06 2005-02-04 β crystalline form of perindopril tert-butylamine salt

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0008792 2000-07-06
FR0008792A FR2811319B1 (fr) 2000-07-06 2000-07-06 Nouvelle forme cristalline beta du sel de tert-butylamine du perindopril, son procede de preparation et les compositions pharmaceutiques qui la contiennent
PCT/FR2001/002168 WO2001087836A1 (fr) 2000-07-06 2001-07-06 Nouvelle forme cristalline $g(b) du sel de tert-butylamine du perindopril, son procede de preparation, et les compositions pharmaceutiques qui la contiennent

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US11/052,489 Continuation US7259181B2 (en) 2000-07-06 2005-02-04 β crystalline form of perindopril tert-butylamine salt

Publications (1)

Publication Number Publication Date
US20040029813A1 true US20040029813A1 (en) 2004-02-12

Family

ID=8852171

Family Applications (2)

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US10/312,902 Abandoned US20040029813A1 (en) 2000-07-06 2001-07-06 Novel $g(beta crystalline form of perindopril tert-butylamine salt, preparation method, and pharmaceutical compositions containing same
US11/052,489 Expired - Fee Related US7259181B2 (en) 2000-07-06 2005-02-04 β crystalline form of perindopril tert-butylamine salt

Family Applications After (1)

Application Number Title Priority Date Filing Date
US11/052,489 Expired - Fee Related US7259181B2 (en) 2000-07-06 2005-02-04 β crystalline form of perindopril tert-butylamine salt

Country Status (36)

Country Link
US (2) US20040029813A1 (ja)
EP (2) EP1294689B1 (ja)
JP (2) JP3592297B2 (ja)
KR (1) KR100513571B1 (ja)
CN (1) CN1328260C (ja)
AP (1) AP1407A (ja)
AR (1) AR029571A1 (ja)
AT (1) ATE324367T1 (ja)
AU (2) AU7641901A (ja)
BG (1) BG66131B1 (ja)
BR (1) BR0112244A (ja)
CA (1) CA2415442C (ja)
CZ (1) CZ301765B6 (ja)
DE (1) DE60119107T2 (ja)
DK (1) DK1294689T3 (ja)
EA (1) EA004874B1 (ja)
EE (1) EE05285B1 (ja)
ES (1) ES2262666T3 (ja)
FR (1) FR2811319B1 (ja)
GE (1) GEP20043360B (ja)
HK (1) HK1058200A1 (ja)
HR (2) HRP20030079B8 (ja)
HU (1) HU227673B1 (ja)
ME (1) ME00440B (ja)
MX (1) MXPA02012921A (ja)
NO (1) NO323446B1 (ja)
NZ (1) NZ523234A (ja)
OA (1) OA12305A (ja)
PL (1) PL348493A1 (ja)
PT (1) PT1294689E (ja)
RS (1) RS51717B (ja)
SI (1) SI1294689T1 (ja)
SK (1) SK286918B6 (ja)
UA (1) UA57189C2 (ja)
WO (1) WO2001087836A1 (ja)
ZA (1) ZA200300024B (ja)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040248817A1 (en) * 2000-07-06 2004-12-09 Bruno Pfeiffer Gamma crystalline form of perindopril tert-butylamine salt
US20050059609A1 (en) * 2000-07-06 2005-03-17 Bruno Pfeiffer New alpha crystalline form of perindopril tert-butylamine salt
US20070135512A1 (en) * 2003-06-24 2007-06-14 Christoph Strassler Novel crystalline forms of perindopril erbumine
US20070172524A1 (en) * 2004-03-29 2007-07-26 Krka, Tovarna Zdravil, D.D., Novo Mesto Process for preparing a solid pharmaceutical composition
WO2007092758A2 (en) * 2006-02-03 2007-08-16 Dr. Reddy's Laboratories Ltd. Crystalline forms of perindopril erbumine
US20080051584A1 (en) * 2004-05-14 2008-02-28 Les Laboratoires Servier Process For The Preparation Of Perindopril And Salts Thereof
US20100016614A1 (en) * 2005-08-12 2010-01-21 Lek Pharmaceuticals D.D Process for the preparation of perindopril erbumine
AU2007220434B2 (en) * 2006-02-28 2010-10-14 Les Laboratoires Servier Beta-crystalline form of perindopril arginine salt, method for making same, and pharmaceutical compositions containing same
AU2007220435B2 (en) * 2006-02-28 2010-11-04 Les Laboratoires Servier Alpha crystalline form of the arginine salt of perindopril, process for preparing it, and pharmaceutical compositions comprising it
US8470869B2 (en) 2007-06-27 2013-06-25 Krka, Tovarna Zdravil D.D. Novo Mesto Salts of perindopril

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2395195A (en) 2002-11-18 2004-05-19 Cipla Ltd Preparation of perindopril from carboxy-protected precursor, & perindopril monohydrates for use as angiotensin converting enzyme (ACE) inhibitors
WO2005037788A1 (en) * 2003-10-21 2005-04-28 Lupin Ltd. Novel method for preparation of crystalline perindopril erbumine
SI21703A (en) 2004-01-14 2005-08-31 Lek Farmacevtska Druzba Dd Inclusion complexes of perindopril, procedure of their preparation, pharmaceutical compositions containing these complexes and their application in treatment of hypertensia
SI21881A (sl) 2004-10-15 2006-04-30 Diagen, Smartno Pri Ljubljani, D.O.O. Nove kristalne oblike perindopril erbumin hidratov, postopek za njihovo pripravo in farmacevtske oblike, ki vsebujejo te spojine
SG125976A1 (en) * 2005-03-11 2006-10-30 Servier Lab New gama crystalline form of perindopril tert-butylamine salt, a process for its preparation and pharmaceutical compositions containing it
SG125975A1 (en) * 2005-03-11 2006-10-30 Servier Lab New alpha crystalline form of perindopril tert-butylamine salt, a process for its preparation and pharmaceutical compositions containing it
JP2006290825A (ja) * 2005-04-13 2006-10-26 Shiono Chemical Co Ltd アルファ型ペリンドプリルエルブミンの製造法
WO2007017894A2 (en) * 2005-05-05 2007-02-15 Arch Pharmalabs Limited PREPARATION OF NOVEL CRYSTALLINE η(ETA) FORM OF PERINDOPRIL ERBUMINE
MX2008002066A (es) * 2005-08-12 2008-04-16 Sandoz Ag Neuva forma cristalina de perindopril-erbumina.
EP1815857A1 (en) 2006-02-02 2007-08-08 LEK Pharmaceuticals D.D. A pharmaceutical composition comprising perindopril
WO2008050185A2 (en) * 2006-10-26 2008-05-02 Glenmark Pharmaceuticals Limited Novel polymorphs of perindopril erbumine
WO2008120241A2 (en) * 2007-03-29 2008-10-09 Ipca Laboratories Limited Novel alcohol solvates of perindopril erbumine
SI2318365T1 (sl) * 2008-06-24 2016-01-29 Mylan Laboratories Limited Nove polimorfne oblike perindopril (l) - arginina in postopek za pripravo
SI23149A (sl) 2009-09-21 2011-03-31 Silverstone Pharma Nove benzatinske soli ACE inhibitorjev, postopek za njihovo pripravo in njihova uporaba za zdravljenje kardiovaskularnih bolezni
PT105315B (pt) 2010-09-29 2013-01-16 Inst Superior Tecnico Uma nova forma cristalina hidratada de erbumina de perindopril, métodos para a sua preparação e sua utilização em preparações farmacêuticas
CN106432042A (zh) * 2015-08-13 2017-02-22 南京华威医药科技开发有限公司 尼达尼布乙磺酸水合物的药物新晶型
EP3842035A1 (en) 2019-12-23 2021-06-30 KRKA, d.d., Novo mesto Composition for the preparation of perindopril arginine granules, a method for their preparation and pharmaceutical composition comprising the granules

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4914214A (en) * 1987-09-17 1990-04-03 Adir Et Cie Process for the industrial synthesis of perindopril

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2771010B1 (fr) * 1997-11-19 2003-08-15 Adir Utilisation d'une combinaison d'un inhibiteur de l'enzyme de conversion de l'angiotensine et d'un diuretique pour le traitement des desordres microcirculatoires
FR2811320B1 (fr) * 2000-07-06 2002-08-23 Adir Nouvelle forme cristalline alpha du sel de tert-butylamine du perindopril, son procede de preparation et les compositions pharmaceutiques qui la contiennent
FR2811318B1 (fr) * 2000-07-06 2002-08-23 Adir Nouvelle forme cristalline gamma du sel de tert-butylamine du perindopril, son procede de preparation et les compositions pharmaceutiques qui la contiennent

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4914214A (en) * 1987-09-17 1990-04-03 Adir Et Cie Process for the industrial synthesis of perindopril

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050059609A1 (en) * 2000-07-06 2005-03-17 Bruno Pfeiffer New alpha crystalline form of perindopril tert-butylamine salt
US20040248817A1 (en) * 2000-07-06 2004-12-09 Bruno Pfeiffer Gamma crystalline form of perindopril tert-butylamine salt
US7981921B2 (en) 2003-06-24 2011-07-19 Les Laboratoires Servier Crystalline forms of perindopril erbumine
US20070135512A1 (en) * 2003-06-24 2007-06-14 Christoph Strassler Novel crystalline forms of perindopril erbumine
US7705046B2 (en) 2003-06-24 2010-04-27 Les Laboratoires Servier Crystalline forms of perindopril erbumine
US20100160404A1 (en) * 2003-06-24 2010-06-24 Christoph Strassler New crystalline forms of perindopril erbumine
US20070172524A1 (en) * 2004-03-29 2007-07-26 Krka, Tovarna Zdravil, D.D., Novo Mesto Process for preparing a solid pharmaceutical composition
EP1729739B1 (en) 2004-03-29 2016-09-28 Les Laboratoires Servier Process for preparing a solid pharmaceutical composition
US20100172995A1 (en) * 2004-03-29 2010-07-08 Les Laboratoires Servier Process For Preparing A Solid Pharmaceutical Composition
US20080051584A1 (en) * 2004-05-14 2008-02-28 Les Laboratoires Servier Process For The Preparation Of Perindopril And Salts Thereof
US7674814B2 (en) 2004-05-14 2010-03-09 Les Laboratoires Servier Process for the preparation of perindopril and salts thereof
US20100016614A1 (en) * 2005-08-12 2010-01-21 Lek Pharmaceuticals D.D Process for the preparation of perindopril erbumine
WO2007092758A2 (en) * 2006-02-03 2007-08-16 Dr. Reddy's Laboratories Ltd. Crystalline forms of perindopril erbumine
WO2007092758A3 (en) * 2006-02-03 2008-06-19 Reddys Lab Ltd Dr Crystalline forms of perindopril erbumine
AU2007220435B2 (en) * 2006-02-28 2010-11-04 Les Laboratoires Servier Alpha crystalline form of the arginine salt of perindopril, process for preparing it, and pharmaceutical compositions comprising it
AU2007220434B2 (en) * 2006-02-28 2010-10-14 Les Laboratoires Servier Beta-crystalline form of perindopril arginine salt, method for making same, and pharmaceutical compositions containing same
US8470869B2 (en) 2007-06-27 2013-06-25 Krka, Tovarna Zdravil D.D. Novo Mesto Salts of perindopril

Also Published As

Publication number Publication date
NZ523234A (en) 2005-01-28
UA57189C2 (uk) 2003-06-16
EA004874B1 (ru) 2004-08-26
JP3592297B2 (ja) 2004-11-24
EE200300002A (et) 2004-08-16
HUP0102813A2 (hu) 2002-03-28
WO2001087836A1 (fr) 2001-11-22
EP1294689B1 (fr) 2006-04-26
FR2811319A1 (fr) 2002-01-11
ME00440B (me) 2011-10-10
DE60119107D1 (de) 2006-06-01
FR2811319B1 (fr) 2002-08-23
ATE324367T1 (de) 2006-05-15
CZ2003356A3 (cs) 2003-05-14
AU7641901A (en) 2001-11-26
OA12305A (en) 2003-12-29
US7259181B2 (en) 2007-08-21
AP2002002710A0 (en) 2002-12-31
EP1676839A2 (fr) 2006-07-05
GEP20043360B (en) 2004-06-10
PT1294689E (pt) 2006-07-31
KR20030016368A (ko) 2003-02-26
MXPA02012921A (es) 2004-07-30
HU227673B1 (hu) 2011-11-28
EE05285B1 (et) 2010-04-15
CZ301765B6 (cs) 2010-06-16
HU0102813D0 (en) 2001-09-28
CA2415442C (fr) 2009-01-27
US20050203165A1 (en) 2005-09-15
SK1482003A3 (en) 2003-06-03
JP2003533508A (ja) 2003-11-11
CA2415442A1 (fr) 2001-11-22
NO323446B1 (no) 2007-05-07
HUP0102813A3 (en) 2003-12-29
ES2262666T3 (es) 2006-12-01
NO20030050L (no) 2003-01-06
PL348493A1 (en) 2002-01-14
EP1676839A3 (fr) 2006-11-08
AU2001276419B2 (en) 2006-11-16
KR100513571B1 (ko) 2005-09-09
HRP20060361A2 (en) 2008-06-30
YU100502A (sh) 2003-08-29
RS51717B (sr) 2011-10-31
DK1294689T3 (da) 2006-08-28
EA200300103A1 (ru) 2003-06-26
CN1440388A (zh) 2003-09-03
HRP20030079B1 (en) 2007-12-31
SK286918B6 (sk) 2009-07-06
HRP20030079A2 (en) 2003-04-30
DE60119107T2 (de) 2006-12-07
HK1058200A1 (en) 2004-05-07
BR0112244A (pt) 2003-06-24
ZA200300024B (en) 2004-02-05
AP1407A (en) 2005-05-30
AR029571A1 (es) 2003-07-02
BG107533A (bg) 2003-11-28
CN1328260C (zh) 2007-07-25
HRP20060361A8 (en) 2008-07-31
EP1294689A1 (fr) 2003-03-26
SI1294689T1 (sl) 2006-08-31
NO20030050D0 (no) 2003-01-06
HRP20030079B8 (en) 2008-09-30
BG66131B1 (bg) 2011-06-30
JP2005002121A (ja) 2005-01-06

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