SK285604B6 - Spôsob prípravy citalopramu, farmaceutický prostriedok s obsahom citalopramu, medziprodukt a jeho použitie - Google Patents

Spôsob prípravy citalopramu, farmaceutický prostriedok s obsahom citalopramu, medziprodukt a jeho použitie Download PDF

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Publication number
SK285604B6
SK285604B6 SK1440-2001A SK14402001A SK285604B6 SK 285604 B6 SK285604 B6 SK 285604B6 SK 14402001 A SK14402001 A SK 14402001A SK 285604 B6 SK285604 B6 SK 285604B6
Authority
SK
Slovakia
Prior art keywords
formula
citalopram
compound
process according
acid
Prior art date
Application number
SK1440-2001A
Other languages
English (en)
Slovak (sk)
Other versions
SK14402001A3 (sk
Inventor
Hans Petersen
Original Assignee
H. Lundbeck A/S
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=8156954&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=SK285604(B6) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by H. Lundbeck A/S filed Critical H. Lundbeck A/S
Publication of SK14402001A3 publication Critical patent/SK14402001A3/sk
Publication of SK285604B6 publication Critical patent/SK285604B6/sk

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/87Benzo [c] furans; Hydrogenated benzo [c] furans
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/335Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A61K31/343Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/24Antidepressants
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D263/00Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/18Oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Neurology (AREA)
  • Pain & Pain Management (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Psychiatry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Steroid Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
SK1440-2001A 1999-04-14 1999-04-14 Spôsob prípravy citalopramu, farmaceutický prostriedok s obsahom citalopramu, medziprodukt a jeho použitie SK285604B6 (sk)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/DK1999/000210 WO1999030548A2 (fr) 1999-04-14 1999-04-14 Procede de preparation de la citaloprame

Publications (2)

Publication Number Publication Date
SK14402001A3 SK14402001A3 (sk) 2002-04-04
SK285604B6 true SK285604B6 (sk) 2007-04-05

Family

ID=8156954

Family Applications (1)

Application Number Title Priority Date Filing Date
SK1440-2001A SK285604B6 (sk) 1999-04-14 1999-04-14 Spôsob prípravy citalopramu, farmaceutický prostriedok s obsahom citalopramu, medziprodukt a jeho použitie

Country Status (29)

Country Link
US (2) US6849749B2 (fr)
EP (1) EP1173431B2 (fr)
JP (1) JP3798940B2 (fr)
KR (1) KR100604156B1 (fr)
CN (1) CN1142926C (fr)
AR (1) AR018204A1 (fr)
AT (1) ATE237604T1 (fr)
AU (1) AU759716B2 (fr)
BR (1) BR9917346A (fr)
CA (1) CA2291129C (fr)
CZ (1) CZ296537B6 (fr)
DE (1) DE69907037T3 (fr)
DK (1) DK1173431T4 (fr)
EA (1) EA004033B1 (fr)
ES (1) ES2195554T5 (fr)
HK (1) HK1048122B (fr)
HU (1) HU227473B1 (fr)
IL (1) IL145615A0 (fr)
IS (1) IS2697B (fr)
IT (1) ITMI991580A1 (fr)
MX (1) MXPA01010134A (fr)
NO (1) NO327719B1 (fr)
NZ (1) NZ514671A (fr)
PL (1) PL198024B1 (fr)
PT (1) PT1173431E (fr)
SI (1) SI1173431T2 (fr)
SK (1) SK285604B6 (fr)
TR (1) TR200102957T2 (fr)
WO (1) WO1999030548A2 (fr)

Families Citing this family (45)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BR9915158B1 (pt) 1998-10-20 2012-02-22 método para preparação de citalopram, e, compostos da fórmula geral viii, ix e iv, ou qualquer de seus enantiÈmeros e sais com adição de ácido do mesmo.
DK1140886T3 (da) 1998-12-23 2003-07-28 Lundbeck & Co As H Fremgangsmåde til fremstilling af 5-cyanophtalid
AR022329A1 (es) 1999-01-29 2002-09-04 Lundbeck & Co As H Metodo para la preparacion de 5-cianoftalida
CZ296537B6 (cs) 1999-04-14 2006-04-12 H. Lundbeck A/S Zpusob výroby citalopramu a meziprodukty
ITMI991581A1 (it) * 1999-06-25 2001-01-15 Lundbeck & Co As H Metodo per la preparazione di citalopram
ITMI991579A1 (it) 1999-06-25 2001-01-15 Lundbeck & Co As H Metodo per la preparazione di citalopram
AR021155A1 (es) * 1999-07-08 2002-06-12 Lundbeck & Co As H Tratamiento de desordenes neuroticos
EP1228056B1 (fr) 1999-10-25 2004-09-22 H. Lundbeck A/S Procede de preparation de citaloprame
TR200401456T1 (tr) * 1999-10-25 2005-04-21 H. Lundbeck A/S Sitalopram hazırlanması için yöntem.
US6310222B1 (en) 1999-11-01 2001-10-30 Sumika Fine Chemicals Co., Ltd. Production method of 5-phthalancarbonitrile compound, intermediate therefor and production method of the intermediate
AR026063A1 (es) 1999-11-01 2002-12-26 Lundbeck & Co As H Metodo para la preparacion de 5-carboxiftalida.
HUP0203635A3 (en) 1999-12-28 2005-02-28 Lundbeck & Co As H Method for the preparation of citalopram
CN1211377C (zh) 1999-12-30 2005-07-20 H.隆德贝克有限公司 西酞普兰的制备方法
ATE252570T1 (de) 2000-01-14 2003-11-15 Lundbeck & Co As H Verfahren zur herstellung von 5-cyanophthalid
US6433196B1 (en) 2000-02-17 2002-08-13 Sumika Fine Chemicals Co., Ltd. Production method of citalopram, intermediate therefor and production method of the intermediate
NL1017415C1 (nl) 2000-02-24 2001-05-18 Lundbeck & Co As H Werkwijze voor de bereiding van Citalopram.
IES20010143A2 (en) * 2000-02-24 2001-07-25 Lundbeck & Co As H Method for the preparation of citalopram
NL1017417C1 (nl) 2000-03-03 2001-03-16 Lundbeck & Co As H Werkwijze voor de bereiding van Citalopram.
GB0005477D0 (en) * 2000-03-07 2000-04-26 Resolution Chemicals Limited Process for the preparation of citalopram
HUP0300273A2 (hu) 2000-03-13 2003-06-28 H. Lundbeck A/S Eljárás 5-szubsztituált 1-(4-fluorfenil)-1,3-dihidroizobenzofurán-származékok lépésenkénti alkilezésére
IES20010206A2 (en) 2000-03-13 2002-03-06 Lundbeck & Co As H Method for the preparation of citalopram
BR0109176A (pt) 2000-03-13 2003-04-22 Lundbeck & Co As H Método para preparação de citalopram e composto da fórmula
GB2357762B (en) 2000-03-13 2002-01-30 Lundbeck & Co As H Crystalline base of citalopram
DK1265882T3 (da) 2000-03-14 2004-06-01 Lundbeck & Co As H Fremgangsmåde til fremstilling af citalopram
TR200202168T2 (tr) * 2000-03-16 2002-12-23 H. Lundbeck A/S 5-Siyano-1-(4-Florofenil)-1,3-Dihidroizobenzofuranların preparasyon metodu
AR032455A1 (es) 2000-05-12 2003-11-12 Lundbeck & Co As H Metodo para la preparacion de citalopram, un intermediario empleado en el metodo, un metodo para la preparacion del intermediario empleado en el metodo y composicion farmaceutica antidepresiva
FI20011622A (fi) 2000-08-18 2002-02-19 Lundbeck & Co As H Menetelmä sitalopraamin valmistamiseksi
IT1319686B1 (it) * 2000-12-12 2003-10-23 C D Farmasint S R L Procedimento di preparazione di citalopram.
CA2360303C (fr) 2000-12-22 2003-08-12 Marco Villa Procede de preparation de citalopram pur
SK284418B6 (sk) 2000-12-28 2005-04-01 H. Lundbeck A/S Spôsob výroby citalopramu
EP1355897A1 (fr) 2001-01-30 2003-10-29 Orion Corporation Fermion Procede de preparation de 1-(3-dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile
GB0105627D0 (en) * 2001-03-07 2001-04-25 Cipla Ltd Preparation of phthalanes
CN1509169A (zh) * 2001-05-01 2004-06-30 H��¡�±������޹�˾ 对映体纯艾司西酞普兰的用途
JP2005525993A (ja) 2001-07-31 2005-09-02 ハー・ルンドベック・アクチエゼルスカベット エスシタロプラムを含む結晶性組成物
DE60108105T2 (de) * 2001-08-02 2005-12-08 Infosint Sa Verfahren zur Herstellung von 5-substituierten Isobenzofuranen
IS7239A (is) * 2001-12-14 2004-04-29 H. Lundbeck A/S Aðferð til framleiðslu á essítalóprami
US7148364B2 (en) 2002-01-07 2006-12-12 Sun Pharmaceutical Industries Process for the preparation of 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofuran carbonitrile
PE20040991A1 (es) 2002-08-12 2004-12-27 Lundbeck & Co As H Separacion de intermediarios para la preparacion de escitalopram
GB2385051B (en) * 2002-08-29 2003-12-24 Max India Ltd Improved process for the preparation of 5-substituted-1 (4-fluorophenyl)-1,3-dihydro isobenzofurans
US6812355B2 (en) 2002-10-22 2004-11-02 Sekhsaria Chemicals Limited Process for the manufacture of citalopram hydrobromide from 5-bromophthalide
TR200504022T1 (tr) * 2003-03-24 2006-08-21 Hetero Drugs Limited (S)-sitalopram oksalatın yeni sıvı kristal formları.
EP1486492A3 (fr) 2003-06-10 2005-02-23 Sun Pharmaceuticals Industries Ltd. Un procédé de hydrogenolyse de [1-(3-dimethylamino)propyl)]-1-(4-fluorophenyl)-1,3-dihydro-5-halo-isobenzofurane
EP1797060A2 (fr) 2004-08-23 2007-06-20 Sun Pharmaceutical Industries Limited Procede de preparation de citalopram et d'enantiomeres
CN111533662B (zh) * 2020-04-07 2022-08-23 福建海西新药创制有限公司 一种西酞普兰中间体的合成方法
CN114763343A (zh) * 2021-01-14 2022-07-19 浙江华海药业股份有限公司 一种西酞普兰或s-西酞普兰的纯化方法

Family Cites Families (43)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1143702A (fr) * 1965-03-18
GB1526331A (en) * 1976-01-14 1978-09-27 Kefalas As Phthalanes
GB8419963D0 (en) 1984-08-06 1984-09-12 Lundbeck & Co As H Intermediate compound and method
GB8814057D0 (en) * 1988-06-14 1988-07-20 Lundbeck & Co As H New enantiomers & their isolation
DK213290D0 (da) 1990-09-06 1990-09-06 Lundbeck & Co As H Treatment of cerebrovascular disorders
DE19626659A1 (de) * 1996-07-03 1998-01-08 Basf Ag Verfahren zur Herstellung von Phthaliden
DE19627697A1 (de) * 1996-07-10 1998-01-15 Basf Ag Verfahren zur Herstellung von Phthaliden
ZA9711376B (en) 1996-12-20 1998-07-21 Lundbeck & Co As H Indole or dihydroindole derivatives
DE19706648A1 (de) 1997-02-20 1998-08-27 Bayer Ag Verfahren zur Herstellung von aromatischen Nitrilen
NZ501737A (en) * 1997-07-08 2001-10-26 H Method for the preparation of citalopram using Grignard reagent 4-halogen-fluorophenyl and 3-halogen-N,N-dimethyl-propylamine
UA62985C2 (en) * 1997-11-10 2004-01-15 Lunnbeck As H A method for the preparation of citalopram
SK283907B6 (sk) * 1997-11-11 2004-04-06 H. Lundbeck A/S Spôsob výroby citalopramu a medziprodukty
BR9915158B1 (pt) 1998-10-20 2012-02-22 método para preparação de citalopram, e, compostos da fórmula geral viii, ix e iv, ou qualquer de seus enantiÈmeros e sais com adição de ácido do mesmo.
DK1140886T3 (da) 1998-12-23 2003-07-28 Lundbeck & Co As H Fremgangsmåde til fremstilling af 5-cyanophtalid
AR022329A1 (es) 1999-01-29 2002-09-04 Lundbeck & Co As H Metodo para la preparacion de 5-cianoftalida
US6331628B1 (en) 1999-03-29 2001-12-18 Nissan Chemical Industries, Ltd. Process for the preparation of benzonitrile compounds
CZ296537B6 (cs) 1999-04-14 2006-04-12 H. Lundbeck A/S Zpusob výroby citalopramu a meziprodukty
ITMI991579A1 (it) 1999-06-25 2001-01-15 Lundbeck & Co As H Metodo per la preparazione di citalopram
ITMI991581A1 (it) 1999-06-25 2001-01-15 Lundbeck & Co As H Metodo per la preparazione di citalopram
ITMI991486A1 (it) 1999-07-06 2001-01-06 Vis Farmaceutici S P A Processo per la sintesi di citalopram
EP1228056B1 (fr) * 1999-10-25 2004-09-22 H. Lundbeck A/S Procede de preparation de citaloprame
JP2003512991A (ja) 1999-10-29 2003-04-08 エクソンモービル リサーチ アンド エンジニアリング カンパニー 微粒子触媒を用いる接触部分酸化方法
AR026063A1 (es) 1999-11-01 2002-12-26 Lundbeck & Co As H Metodo para la preparacion de 5-carboxiftalida.
US6310222B1 (en) 1999-11-01 2001-10-30 Sumika Fine Chemicals Co., Ltd. Production method of 5-phthalancarbonitrile compound, intermediate therefor and production method of the intermediate
HUP0203635A3 (en) 1999-12-28 2005-02-28 Lundbeck & Co As H Method for the preparation of citalopram
CN1211377C (zh) 1999-12-30 2005-07-20 H.隆德贝克有限公司 西酞普兰的制备方法
ATE252570T1 (de) 2000-01-14 2003-11-15 Lundbeck & Co As H Verfahren zur herstellung von 5-cyanophthalid
US6433196B1 (en) 2000-02-17 2002-08-13 Sumika Fine Chemicals Co., Ltd. Production method of citalopram, intermediate therefor and production method of the intermediate
IES20010143A2 (en) * 2000-02-24 2001-07-25 Lundbeck & Co As H Method for the preparation of citalopram
NL1017415C1 (nl) * 2000-02-24 2001-05-18 Lundbeck & Co As H Werkwijze voor de bereiding van Citalopram.
NL1017417C1 (nl) 2000-03-03 2001-03-16 Lundbeck & Co As H Werkwijze voor de bereiding van Citalopram.
BR0109176A (pt) 2000-03-13 2003-04-22 Lundbeck & Co As H Método para preparação de citalopram e composto da fórmula
IES20010206A2 (en) 2000-03-13 2002-03-06 Lundbeck & Co As H Method for the preparation of citalopram
HUP0300273A2 (hu) 2000-03-13 2003-06-28 H. Lundbeck A/S Eljárás 5-szubsztituált 1-(4-fluorfenil)-1,3-dihidroizobenzofurán-származékok lépésenkénti alkilezésére
GB2357762B (en) 2000-03-13 2002-01-30 Lundbeck & Co As H Crystalline base of citalopram
DK1265882T3 (da) 2000-03-14 2004-06-01 Lundbeck & Co As H Fremgangsmåde til fremstilling af citalopram
TR200202168T2 (tr) 2000-03-16 2002-12-23 H. Lundbeck A/S 5-Siyano-1-(4-Florofenil)-1,3-Dihidroizobenzofuranların preparasyon metodu
AR032455A1 (es) 2000-05-12 2003-11-12 Lundbeck & Co As H Metodo para la preparacion de citalopram, un intermediario empleado en el metodo, un metodo para la preparacion del intermediario empleado en el metodo y composicion farmaceutica antidepresiva
AU2001272368A1 (en) 2000-07-06 2002-01-21 H. Lundbeck, A/S Method for the preparation of citalopram
FI20011622A (fi) 2000-08-18 2002-02-19 Lundbeck & Co As H Menetelmä sitalopraamin valmistamiseksi
CA2360303C (fr) 2000-12-22 2003-08-12 Marco Villa Procede de preparation de citalopram pur
SK284418B6 (sk) 2000-12-28 2005-04-01 H. Lundbeck A/S Spôsob výroby citalopramu
JP2005525993A (ja) 2001-07-31 2005-09-02 ハー・ルンドベック・アクチエゼルスカベット エスシタロプラムを含む結晶性組成物

Also Published As

Publication number Publication date
TR200102957T2 (tr) 2004-12-21
DE69907037D1 (de) 2003-05-22
US20050124817A1 (en) 2005-06-09
CN1359382A (zh) 2002-07-17
MXPA01010134A (es) 2002-04-15
HK1048122B (zh) 2005-01-14
JP3798940B2 (ja) 2006-07-19
SK14402001A3 (sk) 2002-04-04
NZ514671A (en) 2003-10-31
DE69907037T2 (de) 2004-01-29
DE69907037T3 (de) 2010-02-18
IS6091A (is) 2001-09-28
AR018204A1 (es) 2001-10-31
WO1999030548B1 (fr) 2000-03-16
KR100604156B1 (ko) 2006-07-25
NO20015017L (no) 2001-10-15
AU759716B2 (en) 2003-04-17
AU3137899A (en) 1999-07-05
ATE237604T1 (de) 2003-05-15
HUP0200678A2 (hu) 2002-07-29
WO1999030548A3 (fr) 2000-02-10
US7030252B2 (en) 2006-04-18
NO20015017D0 (no) 2001-10-15
ES2195554T3 (es) 2003-12-01
BR9917346A (pt) 2002-02-26
PT1173431E (pt) 2003-09-30
CZ296537B6 (cs) 2006-04-12
JP2002509864A (ja) 2002-04-02
EA004033B1 (ru) 2003-12-25
DK1173431T4 (da) 2010-01-04
EP1173431B1 (fr) 2003-04-16
PL350803A1 (en) 2003-02-10
EP1173431B2 (fr) 2009-08-26
HU227473B1 (en) 2011-07-28
US20020040153A1 (en) 2002-04-04
CA2291129A1 (fr) 1999-06-24
DK1173431T3 (da) 2003-08-04
ITMI991580A0 (it) 1999-07-15
IL145615A0 (en) 2002-06-30
PL198024B1 (pl) 2008-05-30
CN1142926C (zh) 2004-03-24
WO1999030548A2 (fr) 1999-06-24
KR20010112421A (ko) 2001-12-20
CZ20013693A3 (cs) 2002-02-13
HUP0200678A3 (en) 2002-09-30
EA200101081A1 (ru) 2002-04-25
US6849749B2 (en) 2005-02-01
ITMI991580A1 (it) 2001-01-15
CA2291129C (fr) 2002-10-22
SI1173431T2 (sl) 2009-12-31
IS2697B (is) 2010-11-15
SI1173431T1 (en) 2003-08-31
HK1048122A1 (en) 2003-03-21
ES2195554T5 (es) 2010-02-02
NO327719B1 (no) 2009-09-14
EP1173431A2 (fr) 2002-01-23

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Legal Events

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MM4A Patent lapsed due to non-payment of maintenance fees

Effective date: 20140414