CA2450961C - Crystalline anticholinergic, processes for preparing it and its use for preparing a pharmaceutical composition - Google Patents

Crystalline anticholinergic, processes for preparing it and its use for preparing a pharmaceutical composition Download PDF

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Publication number
CA2450961C
CA2450961C CA2450961A CA2450961A CA2450961C CA 2450961 C CA2450961 C CA 2450961C CA 2450961 A CA2450961 A CA 2450961A CA 2450961 A CA2450961 A CA 2450961A CA 2450961 C CA2450961 C CA 2450961C
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CA
Canada
Prior art keywords
tiotropium bromide
anhydrous
preparing
crystalline
crystalline tiotropium
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.)
Expired - Fee Related
Application number
CA2450961A
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English (en)
French (fr)
Other versions
CA2450961A1 (en
Inventor
Peter Sieger
Ulrike Werthmann
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.)
Boehringer Ingelheim Pharma GmbH and Co KG
Original Assignee
Boehringer Ingelheim Pharma GmbH and Co KG
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 Boehringer Ingelheim Pharma GmbH and Co KG filed Critical Boehringer Ingelheim Pharma GmbH and Co KG
Publication of CA2450961A1 publication Critical patent/CA2450961A1/en
Application granted granted Critical
Publication of CA2450961C publication Critical patent/CA2450961C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D451/00Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
    • C07D451/06Oxygen atoms
    • C07D451/10Oxygen atoms acylated by aliphatic or araliphatic carboxylic acids, e.g. atropine, scopolamine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/468-Azabicyclo [3.2.1] octane; Derivatives thereof, e.g. atropine, cocaine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • A61P11/06Antiasthmatics

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pulmonology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Emergency Medicine (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicinal Preparation (AREA)
  • Steroid Compounds (AREA)
CA2450961A 2001-06-22 2002-06-08 Crystalline anticholinergic, processes for preparing it and its use for preparing a pharmaceutical composition Expired - Fee Related CA2450961C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE10129710 2001-06-22
DE10129710.6 2001-06-22
DE10215436 2002-04-08
DE10215436.8 2002-04-08
PCT/EP2002/006291 WO2003000265A1 (de) 2001-06-22 2002-06-08 Kristallines anticholinergikum, verfahren zu dessen herstellung und dessen verwendung zur herstellung eines arzneimittels

Publications (2)

Publication Number Publication Date
CA2450961A1 CA2450961A1 (en) 2003-01-03
CA2450961C true CA2450961C (en) 2010-03-30

Family

ID=26009556

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2450961A Expired - Fee Related CA2450961C (en) 2001-06-22 2002-06-08 Crystalline anticholinergic, processes for preparing it and its use for preparing a pharmaceutical composition

Country Status (37)

Country Link
EP (1) EP1401445B1 (enExample)
JP (1) JP2005504015A (enExample)
KR (2) KR101011353B1 (enExample)
CN (1) CN100586948C (enExample)
AR (1) AR037491A1 (enExample)
AT (1) ATE337006T1 (enExample)
AU (1) AU2002345016B2 (enExample)
BG (1) BG66303B1 (enExample)
BR (1) BR0210537A (enExample)
CA (1) CA2450961C (enExample)
CO (1) CO5550423A2 (enExample)
CY (1) CY1105223T1 (enExample)
CZ (1) CZ302786B6 (enExample)
DE (1) DE50207943D1 (enExample)
DK (1) DK1401445T3 (enExample)
EA (1) EA005813B1 (enExample)
EE (1) EE05316B1 (enExample)
EG (1) EG24851A (enExample)
ES (1) ES2271280T3 (enExample)
HR (1) HRP20031066B1 (enExample)
HU (1) HUP0400333A3 (enExample)
IL (2) IL159238A0 (enExample)
ME (1) ME00412B (enExample)
MX (1) MXPA03011718A (enExample)
MY (1) MY122779A (enExample)
NO (1) NO334301B1 (enExample)
NZ (1) NZ530690A (enExample)
PE (2) PE20030130A1 (enExample)
PL (1) PL208137B1 (enExample)
PT (1) PT1401445E (enExample)
RS (1) RS50441B (enExample)
SA (1) SA02230255B1 (enExample)
SI (1) SI1401445T1 (enExample)
SK (1) SK287262B6 (enExample)
TW (2) TWI261589B (enExample)
UY (1) UY27342A1 (enExample)
WO (1) WO2003000265A1 (enExample)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10385078B2 (en) 2014-10-21 2019-08-20 Ariad Pharmaceuticals, Inc. Crystalline forms of 5-chloro-N4-[-2-(dimethylphosphoryl)phenyl]-N2-{2-methoxy-4-[4-(4-methylpiperazin-1-YL) piperidin-1-YL]phenyl}pyrimidine-2,4-diamine

Families Citing this family (58)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10212264A1 (de) 2002-03-20 2003-10-02 Boehringer Ingelheim Pharma Kristallines Mikronisat, Verfahren zu dessen Herstellung und dessen Verwendung zur Herstellung eines Arzneimittels
US7056916B2 (en) 2002-11-15 2006-06-06 Boehringer Ingelheim Pharma Gmbh & Co. Kg Medicaments for the treatment of chronic obstructive pulmonary disease
US20050038004A1 (en) * 2003-07-31 2005-02-17 Robinson Cynthia B. Combination of dehydroepiandrosterone or dehydroepiandrosterone-sulfate with an anticholinergic bronchodilator for treatment of asthma or chronic obstructive pulmonary disease
DE502004010602D1 (de) * 2003-11-03 2010-02-11 Boehringer Ingelheim Pharma Neues kristallines anhydrat mit anticholinerger wirksamkeit
DE102004016179A1 (de) * 2004-03-30 2005-10-20 Boehringer Ingelheim Pharma Verbindungen zur Behandlung von proliferativen Prozessen
PL2422786T3 (pl) 2004-04-22 2015-02-27 Boehringer Ingelheim Int Nowe kombinacje środków leczniczych do leczenia chorób dróg oddechowych
US7220742B2 (en) 2004-05-14 2007-05-22 Boehringer Ingelheim International Gmbh Enantiomerically pure beta agonists, process for the manufacture thereof and use thereof as medicaments
DE102004024454A1 (de) 2004-05-14 2005-12-08 Boehringer Ingelheim Pharma Gmbh & Co. Kg Neue Enantiomerenreine Betaagonisten, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel
ATE427108T1 (de) 2004-08-11 2009-04-15 Boehringer Ingelheim Pharma Anticholinergika enthaltende arzneimittel zur behandlung von krankheiten der ableitenden harnwege
US20060079544A1 (en) * 2004-08-13 2006-04-13 Boehringer Ingelheim International Gmbh Medicaments for the prevention or treatment of alveolar pneumonia comprising an anticholinergic
DE102004048389A1 (de) 2004-10-01 2006-04-06 Boehringer Ingelheim Pharma Gmbh & Co. Kg Modifizierung von Oberflächen von Laktose als Hilfsstoff zur Verwendung für Pulverinhalativa
AU2006239389B2 (en) 2005-04-28 2012-06-28 Boehringer Ingelheim International Gmbh Novel compounds for treating inflammatory diseases
RU2417224C2 (ru) * 2005-05-02 2011-04-27 Бёрингер Ингельхайм Интернациональ Гмбх Новые кристаллические формы тиотропийбромида
RU2007144531A (ru) * 2005-05-02 2009-06-10 БЕРИНГЕР ИНГЕЛЬХАЙМ ИНТЕРНАЦИОНАЛЬ ГмбХ (DE) Новые кристаллические формы тиотропийбромида
DE102005030733A1 (de) 2005-07-01 2007-01-04 Boehringer Ingelheim Pharma Gmbh & Co. Kg Neue Arzneimittelkombinationen zur Behandlung von Atemwegserkrankungen enthaltend langwirksame Beta-2-Agonisten und wenigstens einen weiteren Wirkstoff
KR101360803B1 (ko) 2005-08-15 2014-02-11 베링거 인겔하임 인터내셔날 게엠베하 베타모방제의 제조방법
US20070086957A1 (en) * 2005-10-10 2007-04-19 Thierry Bouyssou Combination of medicaments for the treatment of respiratory diseases
US7423146B2 (en) 2005-11-09 2008-09-09 Boehringer Ingelheim International Gmbh Process for the manufacturing of pharmaceutically active 3,1-benzoxazine-2-ones
US9108962B2 (en) 2005-12-19 2015-08-18 Sicor, Inc. Forms of tiotropium bromide and processes for preparation thereof
BRPI0608427A2 (pt) * 2005-12-19 2009-12-29 Sicor Inc novas formas de brometo de tiotrópio e processos para seu preparo
CN100999521B (zh) * 2006-01-13 2010-12-08 江苏正大天晴药业股份有限公司 结晶性抗胆碱药噻托溴铵
MX2007012313A (es) 2006-04-19 2007-11-21 Boehringer Ingelheim Int Dihidrotienopirimidinas para el tratamiento de enfermedades inflamatorias.
EP1847543A1 (de) 2006-04-19 2007-10-24 Boehringer Ingelheim Pharma GmbH & Co. KG Dihydrothienopyrimidine zur Behandlung von entzündlichen Erkrankungen
CA2660186A1 (en) 2006-08-07 2008-02-14 Boehringer Ingelheim International Gmbh Pharmaceutical combinations for the treatment of respiratory diseases
PE20080610A1 (es) 2006-08-22 2008-07-15 Boehringer Ingelheim Int Nuevos beta-agonistas enantiomericamente puros, procedimientos para su preparacion y uso como medicamentos
GB0716026D0 (en) 2007-08-16 2007-09-26 Norton Healthcare Ltd An inhalable medicament
PT2215092E (pt) 2007-10-19 2012-04-10 Boehringer Ingelheim Int Piperidino-di-hidrotienopirimidinas substituídas
EP2093219A1 (de) 2008-02-22 2009-08-26 Boehringer Ingelheim International Gmbh Kristalline, enantiomerenreine Salzform eines Betamimetikums und dessen Verwendung als Arzneimittel
CN102256963B (zh) 2008-12-19 2014-06-11 贝林格尔.英格海姆国际有限公司 作为ccr2受体拮抗剂用于治疗炎症、哮喘和copd的环状嘧啶-4-甲酰胺
EP2403851B1 (en) 2009-03-06 2015-06-17 Mahmut Bilgic New crystalline forms of tiotropium bromide
US20130143905A1 (en) 2009-12-17 2013-06-06 Boehringer Ingelheim International Gmbh Novel antagonists for ccr2 and uses thereof
PL2513093T3 (pl) 2009-12-17 2015-03-31 Centrexion Therapeutics Corp Nowi antagoniści receptora CCR2 i ich zastosowanie
BR112012018865A2 (pt) 2010-01-29 2016-04-12 Boehringer Ingelheim Int naftiridinas substituídas e seu uso como inibidores de quinase syk
JP2013526507A (ja) 2010-05-12 2013-06-24 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング 新規ccr2受容体アンタゴニスト、その製造方法及び薬物としてのその使用
WO2011141477A1 (en) 2010-05-12 2011-11-17 Boehringer Ingelheim International Gmbh New ccr2 receptor antagonists, method for producing the same, and use thereof as medicaments
JP5647339B2 (ja) 2010-05-17 2014-12-24 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング Ccr2アンタゴニスト及びこれらの使用
WO2011147772A1 (en) 2010-05-25 2011-12-01 Boehringer Ingelheim International Gmbh Ccr2 receptor antagonists
JP5721242B2 (ja) 2010-06-01 2015-05-20 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング 新規ccr2アンタゴニスト
TR201007108A2 (tr) * 2010-08-25 2012-03-21 B�Lg�� Mahmut Yeni tiotropyum bromür kristali ve üretim yöntemi.@
JP5959537B2 (ja) 2011-01-28 2016-08-02 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング 置換ピリジニル−ピリミジン及び医薬としてのその使用
TR201101897A2 (tr) 2011-02-28 2012-09-21 Bi̇lgi̇ç Mahmut Tiotropyum bromür içeren kristal madde
TR201102068A2 (tr) 2011-03-03 2012-09-21 Bi̇lgi̇ç Mahmut Tiotropyum bromür içeren kristal maddeler
TR201111589A2 (tr) * 2011-03-03 2012-09-21 Bi̇lgi̇ç Mahmut Tiotropyum bromür susuz kristal formu.
WO2012171863A1 (en) 2011-06-16 2012-12-20 Boehringer Ingelheim International Gmbh New selective ccr2 antagonists
EP2731941B1 (en) 2011-07-15 2019-05-08 Boehringer Ingelheim International GmbH Novel and selective ccr2 antagonists
JP5860960B2 (ja) 2011-07-26 2016-02-16 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング 置換キノリン類及び医薬としてのそれらの使用
US20130059866A1 (en) 2011-08-24 2013-03-07 Boehringer Ingelheim International Gmbh Novel piperidino-dihydrothienopyrimidine sulfoxides and their use for treating copd and asthma
PL2782914T3 (pl) 2011-11-25 2019-01-31 Adverio Pharma Gmbh Sposób wytwarzania podstawionych 5-fluoro-1H-pirazolopirydyn
CZ304368B6 (cs) 2011-11-28 2014-04-02 Zentiva, K.S. Směsný solvát tiotropium bromidu a způsob jeho přípravy
GB201200525D0 (en) 2011-12-19 2012-02-29 Teva Branded Pharmaceutical Prod R & D Inc An inhalable medicament
PT106142B (pt) * 2012-02-10 2014-07-18 Hovione Farmaci Ncia S A Processo para a preparação de brometo de tiotrópio
US9096579B2 (en) 2012-04-20 2015-08-04 Boehringer Ingelheim International Gmbh Amino-indolyl-substituted imidazolyl-pyrimidines and their use as medicaments
EP2897955B1 (en) * 2012-09-11 2019-11-06 Bilgic, Mahmut New tiotropium bromide crystalline form
ME02679B (me) 2012-11-05 2017-06-20 Zentiva Ks Stabilizacija tiotropij solvata
CN104341412A (zh) * 2013-07-29 2015-02-11 天津金耀集团有限公司 一种无水噻托溴铵结晶的制备方法
WO2015140051A1 (en) 2014-03-19 2015-09-24 Boehringer Ingelheim International Gmbh Heteroaryl sik inhibitors
US10034866B2 (en) 2014-06-19 2018-07-31 Teva Branded Pharmaceutical Products R&D, Inc. Inhalable medicament comprising tiotropium
WO2017138896A1 (en) * 2016-02-11 2017-08-17 Sima Patent Ve Lisanslama Hizmetleri Ltd. Şti Crystalline form of tiotropium bromide anhydrate

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5610163A (en) * 1989-09-16 1997-03-11 Boehringer Ingelheim Gmbh Esters of thienyl carboxylic acids and amino alcohols and their quaternization products
DE3931041C2 (de) * 1989-09-16 2000-04-06 Boehringer Ingelheim Kg Ester von Thienylcarbonsäuren mit Aminoalkoholen, ihre Quaternierungsprodukte, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
PL207870B1 (pl) * 2000-10-12 2011-02-28 Boehringer Ingelheim Pharma Krystaliczny monohydrat bromku tiotropium, sposób jego wytwarzania, środek leczniczy i zastosowanie
DE10064816A1 (de) * 2000-12-22 2002-06-27 Boehringer Ingelheim Pharma Verfahren zur Herstellung eines Anticholinergikums

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10385078B2 (en) 2014-10-21 2019-08-20 Ariad Pharmaceuticals, Inc. Crystalline forms of 5-chloro-N4-[-2-(dimethylphosphoryl)phenyl]-N2-{2-methoxy-4-[4-(4-methylpiperazin-1-YL) piperidin-1-YL]phenyl}pyrimidine-2,4-diamine
US10934317B2 (en) 2014-10-21 2021-03-02 Ariad Pharmaceuticals, Inc. Crystalline forms of 5-chloro-N4-[-2-(dimethylphosphoryl) phenyl]-N2-{2-methoxy-4-[4-(4-methylpiperazin-1-yl) piperidin-1-yl] phenyl} pyrimidine-2,4-diamine
US11427605B2 (en) 2014-10-21 2022-08-30 Takeda Pharmaceutical Company Limited Crystalline forms of 5-chloro-N4-[-2-(dimethylphosphoryl) phenyl]-N2-{2-methoxy-4-[4-(4-methylpiperazin-1-yl) piperidin-1-yl] phenyl} pyrimidine-2,4-diamine

Also Published As

Publication number Publication date
MY122779A (en) 2006-05-31
PE20081305A1 (es) 2008-10-01
PL364489A1 (en) 2004-12-13
EP1401445B1 (de) 2006-08-23
CA2450961A1 (en) 2003-01-03
DK1401445T3 (da) 2006-11-27
NO334301B1 (no) 2014-02-03
SA02230255B1 (ar) 2006-10-31
NO20035696D0 (no) 2003-12-19
HK1068540A1 (zh) 2005-04-29
EA200301293A1 (ru) 2004-08-26
CZ302786B6 (cs) 2011-11-09
KR20040018285A (ko) 2004-03-02
EG24851A (en) 2010-10-27
HUP0400333A3 (en) 2012-10-29
SK287262B6 (sk) 2010-04-07
EE05316B1 (et) 2010-08-16
EP1401445A1 (de) 2004-03-31
PT1401445E (pt) 2006-10-31
EA005813B1 (ru) 2005-06-30
NZ530690A (en) 2005-05-27
BR0210537A (pt) 2004-06-22
KR20090031638A (ko) 2009-03-26
ES2271280T3 (es) 2007-04-16
UY27342A1 (es) 2003-02-28
YU99703A (sh) 2006-05-25
PL208137B1 (pl) 2011-03-31
EE200400029A (et) 2004-04-15
JP2005504015A (ja) 2005-02-10
SI1401445T1 (sl) 2007-02-28
ME00412B (me) 2011-10-10
TW200617007A (en) 2006-06-01
BG66303B1 (bg) 2013-03-29
HRP20031066A2 (en) 2004-04-30
CN100586948C (zh) 2010-02-03
TWI261589B (en) 2006-09-11
AU2002345016B2 (en) 2008-04-17
DE50207943D1 (de) 2006-10-05
CN1520294A (zh) 2004-08-11
CY1105223T1 (el) 2010-03-03
WO2003000265A1 (de) 2003-01-03
IL159238A0 (en) 2004-06-01
PE20030130A1 (es) 2003-04-02
ATE337006T1 (de) 2006-09-15
IL159238A (en) 2010-04-15
HRP20031066B1 (en) 2011-10-31
KR101011353B1 (ko) 2011-01-28
CZ2004120A3 (cs) 2004-05-12
CO5550423A2 (es) 2005-08-31
MEP62008A (en) 2011-05-10
RS50441B (sr) 2010-03-02
HUP0400333A2 (hu) 2004-12-28
AR037491A1 (es) 2004-11-17
KR100971616B1 (ko) 2010-07-22
MXPA03011718A (es) 2004-12-06
BG108440A (bg) 2004-08-31
SK522004A3 (en) 2004-06-08

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