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HUP0103417A2 - Eljárás citalopram előállítására - Google Patents

Eljárás citalopram előállítására

Info

Publication number
HUP0103417A2
HUP0103417A2 HU0103417A HUP0103417A HUP0103417A2 HU P0103417 A2 HUP0103417 A2 HU P0103417A2 HU 0103417 A HU0103417 A HU 0103417A HU P0103417 A HUP0103417 A HU P0103417A HU P0103417 A2 HUP0103417 A2 HU P0103417A2
Authority
HU
Hungary
Prior art keywords
citalopram
formula
compound
preparation
isobenzofurancarbonitrile
Prior art date
Application number
HU0103417A
Other languages
English (en)
Inventor
Hans Petersen
Michael Harold Rock
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
Application filed by H. Lundbeck A/S filed Critical H. Lundbeck A/S
Publication of HUP0103417A2 publication Critical patent/HUP0103417A2/hu
Publication of HUP0103417A3 publication Critical patent/HUP0103417A3/hu

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic 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
    • C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2282—Unsaturated compounds used as ligands
    • B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic 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
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic 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
    • A61K31/343—Heterocyclic 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/84—Metals of the iron group
    • B01J2531/847—Nickel

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Inorganic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Neurosurgery (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Epidemiology (AREA)
  • Pain & Pain Management (AREA)
  • Psychiatry (AREA)
  • Hospice & Palliative Care (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Furan Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Steroid Compounds (AREA)

Abstract

A találmány tárgya új eljárás a jól ismert antidepresszáns hatásúvegyület, azaz a citalopram vagy kémiai nevén 1-(3-(dimetilamino)propil]-1-(4-fluorfenil)-1,3-dihidro-5-izobenzofuránkarbonitrilelőállítására. A találmány értelmében úgy járnak el, hogy valamely(IV) általános képletű vegyületet - a képletben R jelentése klór- vagybrómatom - cianidforrással reagáltatnak nikkelkatalizátorjelenlétében, majd a kapott 5-ciano-származékot, azaz az (I) képletűcitalopramot bázisként vagy gyógyászatilag elfogadható sókéntelkülönítik. Ó
HU0103417A 1999-06-25 1999-11-19 Method for preparation of citalopram HUP0103417A3 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DKPA199900921 1999-06-25
PCT/DK1999/000643 WO2000011926A2 (en) 1999-06-25 1999-11-19 Method for the preparation of citalopram

Publications (2)

Publication Number Publication Date
HUP0103417A2 true HUP0103417A2 (hu) 2002-01-28
HUP0103417A3 HUP0103417A3 (en) 2003-01-28

Family

ID=8099044

Family Applications (1)

Application Number Title Priority Date Filing Date
HU0103417A HUP0103417A3 (en) 1999-06-25 1999-11-19 Method for preparation of citalopram

Country Status (36)

Country Link
US (1) US6750358B2 (hu)
EP (1) EP1105382B1 (hu)
JP (1) JP3389571B2 (hu)
KR (1) KR100491369B1 (hu)
CN (1) CN1129593C (hu)
AR (1) AR020573A1 (hu)
AT (3) ATE213237T1 (hu)
AU (2) AU2001100433B4 (hu)
BG (1) BG106190A (hu)
BR (1) BR9917367A (hu)
CA (1) CA2290125C (hu)
CH (1) CH691304A5 (hu)
CZ (1) CZ292174B6 (hu)
DE (2) DE19983486C2 (hu)
DK (1) DK1105382T3 (hu)
EA (1) EA002661B1 (hu)
ES (1) ES2172356T3 (hu)
FI (1) FI108538B (hu)
GB (1) GB2354240B (hu)
HK (1) HK1047745B (hu)
HU (1) HUP0103417A3 (hu)
IL (1) IL145960A0 (hu)
IS (1) IS5862A (hu)
IT (1) ITMI991579A1 (hu)
MX (1) MXPA01010986A (hu)
NO (1) NO20010318L (hu)
NZ (1) NZ514982A (hu)
PL (1) PL345971A1 (hu)
PT (1) PT1105382E (hu)
SE (1) SE516689C2 (hu)
SI (1) SI1105382T1 (hu)
SK (1) SK18412001A3 (hu)
TR (1) TR200103700T2 (hu)
UA (1) UA62023C2 (hu)
WO (1) WO2000011926A2 (hu)
ZA (1) ZA200108855B (hu)

Families Citing this family (39)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SK285530B6 (sk) 1998-12-23 2007-03-01 H. Lundbeck A/S Spôsob prípravy 5-kyanoftalidu
AR022329A1 (es) 1999-01-29 2002-09-04 Lundbeck & Co As H Metodo para la preparacion de 5-cianoftalida
CA2291129C (en) 1999-04-14 2002-10-22 H. Lundbeck A/S Method for the preparation of citalopram
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
DE19983836C1 (de) 1999-10-25 2003-10-23 Lundbeck As Valby H Verfahren zur Herstellung von Citalopram, 4-[1-(4- Fluorphenyl)-methanoyl]-benzonitril-Derivate und Verfahren zu deren Herstellung und deren Verwendung
TR200101874T1 (tr) 1999-10-25 2002-02-21 H. Lundbeck A/S Sitalopram hazırlanması için yöntem
AR026063A1 (es) 1999-11-01 2002-12-26 Lundbeck & Co As H Metodo para la preparacion de 5-carboxiftalida.
CA2395404A1 (en) 1999-12-28 2001-07-05 H. Lundbeck A/S Method for the preparation of citalopram
DK1246813T3 (da) 1999-12-30 2004-03-01 Lundbeck & Co As H Fremgangsmåde til fremstilling af Citalopram
HUP0300343A2 (hu) 2000-01-14 2003-06-28 H. Lundbeck A/S Eljárás 5-cianoftalid előállítására
FR2805812A1 (fr) 2000-02-24 2001-09-07 Lundbeck & Co As H Procede de preparation du 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
KR20020080481A (ko) 2000-03-13 2002-10-23 하. 룬트벡 아크티에 셀스카브 시탈로프람의 제조 방법
GB2357762B (en) * 2000-03-13 2002-01-30 Lundbeck & Co As H Crystalline base of citalopram
JP2003527385A (ja) 2000-03-13 2003-09-16 ハー・ルンドベック・アクチエゼルスカベット ５−置換された１−（４−フルオロフェニル）−１，３−ジヒドロイソベンゾフランの段階的アルキル化法
IES20010206A2 (en) 2000-03-13 2002-03-06 Lundbeck & Co As H Method for the preparation of citalopram
AU2001239213A1 (en) 2000-03-14 2001-09-24 H Lundbeck A/S Method for the preparation of citalopram
AT5093U1 (de) * 2000-03-16 2002-03-25 Lundbeck & Co As H Verfahren zur herstellung von
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
SK3362002A3 (en) * 2000-07-06 2002-08-06 Lundbeck & Co As H Method for the preparation of citalopram
FI20011622L (fi) * 2000-08-18 2002-02-19 Lundbeck & Co As H Menetelmä sitalopraamin valmistamiseksi
BR0106272A (pt) * 2000-12-22 2004-06-15 Lundbeck & Co As H Processo para preparação de citalopram puro
DK1181272T3 (da) * 2000-12-28 2002-12-30 Lundbeck & Co As H Fremgangsmåde til fremstilling af rent citalopram
WO2002060886A1 (en) 2001-01-30 2002-08-08 Orion Corporation, Fermion Process for the preparation of 1-(3-dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile
RU2003130073A (ru) * 2001-03-09 2005-04-10 Ранбакси Лабораторис Лимитед (In) Способ получения циталопрама
DE60217932T2 (de) 2001-07-31 2007-08-30 H. Lundbeck A/S, Valby Kristalline Zusammensetzung enthaltend Escitalopram
AU2003222435A1 (en) 2002-01-07 2003-07-24 Sun Pharmaceutical Industries Limited 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
AU2003223105A1 (en) * 2003-03-24 2004-10-18 Hetero Drugs Limited Novel crystalline forms of (s)-citalopram oxalate
US7019153B2 (en) 2003-06-10 2006-03-28 Sun Pharmaceutical Industries Limited Process for hydrogenolysis of [1-(3-dimethylamino)propyl)]-1-(4-fluorophenyl)-1,3-dihydro-5-halo-isobenzofuran acetamido-3-substituted-3-cephem-4-carboxylic acid
TWI339651B (en) 2004-02-12 2011-04-01 Lundbeck & Co As H Method for the separation of intermediates which may be used for the preparation of escitalopram
JP2006008603A (ja) * 2004-06-25 2006-01-12 Sumitomo Chemical Co Ltd 光学活性シタロプラムの製造方法、その中間体およびその製造方法
EP2141156A1 (en) 2004-08-23 2010-01-06 Sun Pharma Global FZE Process for Preparation of Citalopram and Enantiomers
WO2006103550A1 (en) * 2005-03-31 2006-10-05 Ranbaxy Laboratories Limited Processes for the preparation of citalopram and its intermediate 5-aminophthalide
US7834201B2 (en) 2005-06-22 2010-11-16 H. Lundbeck A/S Crystalline base of escitalopram and orodispersible tablets comprising escitalopram base
TWI347942B (en) 2005-06-22 2011-09-01 Lundbeck & Co As H Crystalline base of escitalopram and orodispersible tablets comprising escitalopram base
EP2017271A1 (en) 2007-07-06 2009-01-21 Aurobindo Pharma Limited Process for the preparation of escitalopram

Family Cites Families (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1143702A (hu) 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
CA2010159A1 (en) 1989-02-21 1990-08-21 James J. Maul Cyanation of haloaromatics utilizing catalysts generated in situ starting with nic1 or nic1 6h 0
US5296507A (en) 1990-09-06 1994-03-22 H.Lundbeck A/S Treatment of cerbrovascular 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
DE19706648A1 (de) 1997-02-20 1998-08-27 Bayer Ag Verfahren zur Herstellung von aromatischen Nitrilen
ES2148120T3 (es) 1997-07-08 2002-01-16 Lundbeck & Co As H Metodo para la preparacion de citalopram.
UA62985C2 (en) 1997-11-10 2004-01-15 Lunnbeck As H A method for the preparation of citalopram
TR200001341T2 (tr) 1997-11-11 2000-11-21 H. Lundbeck A/S Sitalopramın hazırlandığı metot
JP3892667B2 (ja) 1998-10-20 2007-03-14 ハー・ルンドベック・アクチエゼルスカベット シタロプラムの製造方法
SK285530B6 (sk) 1998-12-23 2007-03-01 H. Lundbeck A/S Spôsob prípravy 5-kyanoftalidu
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
CA2291129C (en) 1999-04-14 2002-10-22 H. Lundbeck A/S Method for the preparation of citalopram
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
TR200101874T1 (tr) 1999-10-25 2002-02-21 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
GB0005477D0 (en) 2000-03-07 2000-04-26 Resolution Chemicals Limited Process for the preparation of citalopram
BR0106272A (pt) 2000-12-22 2004-06-15 Lundbeck & Co As H Processo para preparação de citalopram puro
DK1181272T3 (da) 2000-12-28 2002-12-30 Lundbeck & Co As H Fremgangsmåde til fremstilling af rent citalopram

Also Published As

Publication number Publication date
HUP0103417A3 (en) 2003-01-28
WO2000011926A2 (en) 2000-03-09
FI20010154L (fi) 2001-02-09
IL145960A0 (en) 2002-07-25
BG106190A (en) 2002-08-30
EA200101071A1 (ru) 2002-02-28
ITMI991579A0 (it) 1999-07-15
AU2001100433B4 (en) 2002-01-17
JP2002523432A (ja) 2002-07-30
DE69900891D1 (de) 2002-03-21
AT409960B (de) 2002-12-27
FI108538B (fi) 2002-02-15
GB2354240A (en) 2001-03-21
ITMI991579A1 (it) 2001-01-15
EP1105382B1 (en) 2002-02-13
HK1047745B (zh) 2004-09-10
NZ514982A (en) 2004-01-30
SE516689C2 (sv) 2002-02-12
DE19983486C2 (de) 2002-09-05
PL345971A1 (en) 2002-01-14
CA2290125C (en) 2004-08-10
BR9917367A (pt) 2002-03-05
TR200103700T2 (tr) 2002-05-21
KR20020011982A (ko) 2002-02-09
DK1105382T3 (da) 2002-05-27
ES2172356T3 (es) 2002-09-16
NO20010318L (no) 2001-02-20
IS5862A (is) 2001-02-23
CH691304A5 (de) 2001-06-29
PT1105382E (pt) 2002-07-31
ZA200108855B (en) 2002-08-28
CN1356993A (zh) 2002-07-03
CN1129593C (zh) 2003-12-03
GB0101508D0 (en) 2001-03-07
SI1105382T1 (en) 2002-06-30
JP3389571B2 (ja) 2003-03-24
CZ292174B6 (cs) 2003-08-13
SE0100194L (sv) 2001-04-25
AU2001100433A4 (en) 2001-11-01
DE19983486T1 (de) 2001-10-18
AR020573A1 (es) 2002-05-15
CZ2001319A3 (en) 2001-05-16
EP1105382A2 (en) 2001-06-13
HK1047745A1 (en) 2003-03-07
NO20010318D0 (no) 2001-01-19
AT4366U1 (de) 2001-06-25
WO2000011926A3 (en) 2000-06-29
CA2290125A1 (en) 2000-12-25
US6750358B2 (en) 2004-06-15
GB2354240B (en) 2001-05-23
KR100491369B1 (ko) 2005-05-24
US20020061925A1 (en) 2002-05-23
MXPA01010986A (es) 2002-06-04
EA002661B1 (ru) 2002-08-29
ATA904099A (de) 2002-05-15
UA62023C2 (en) 2003-12-15
SK18412001A3 (sk) 2002-05-09
AU1374800A (en) 2000-03-21
ATE213237T1 (de) 2002-02-15
SE0100194D0 (sv) 2001-01-24

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