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DK200100060A - Fremgangsmåde til fremstilling af citalopram - Google Patents

Fremgangsmåde til fremstilling af citalopram Download PDF

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Publication number
DK200100060A
DK200100060A DK200100060A DKPA200100060A DK200100060A DK 200100060 A DK200100060 A DK 200100060A DK 200100060 A DK200100060 A DK 200100060A DK PA200100060 A DKPA200100060 A DK PA200100060A DK 200100060 A DK200100060 A DK 200100060A
Authority
DK
Denmark
Prior art keywords
palladium catalyst
cyanide
citalopram
preparation
comprises reacting
Prior art date
Application number
DK200100060A
Other languages
English (en)
Inventor
Hans Petersen
Michael Harold Rock
Henrik Svane
Original Assignee
Lundbeck & Co As H
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 Lundbeck & Co As H filed Critical Lundbeck & Co As H
Priority to DK200100060A priority Critical patent/DK200100060A/da
Publication of DK200100060A publication Critical patent/DK200100060A/da

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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
    • 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
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/44—Palladium
    • 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
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Psychiatry (AREA)
  • Epidemiology (AREA)
  • Materials Engineering (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)
  • Catalysts (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Steroid Compounds (AREA)

Description

KRAV
1. En fremgangsmåde til fremstilling af citalopram omfattende reaktion af en forbindelse med formlen IV
Figure DK200100060AD00031
hvori R er halogen, eller CF3-(CF2)n-S02-0-, hvori n er et helt tal i området 0-8, med en cyanidkilde i nærvær af en palladiumkatalysator og en katalytisk mængde af Cu+ eller Zn2+, eller med Zn(CN)2 i nærvær af en palladiumkatalysator, og isolering af den tilsvarende 5-cyanoforbindelse, dvs. citalopram
Figure DK200100060AD00032
som basen eller et farmaceutisk acceptabelt salt deraf. 2. Fremgangsmåden ifølge krav 1, hvori cyanidkilden er KCN, NaCN eller (R'4N)CN, hvor R'4 indikerer fire grupper, som kan være ens eller forskellige, og som vælges blandt hydrogen og ligekædet eller forgrenet C,_6 alkyl. 3. Fremgangsmåden ifølge krav 1 eller 2, hvori R er CF3-(CF2)n-S02-0-, hvori n er et helt tal i området 0 to 8, fortrinsvis CF3-S02-0-. 4. Fremgangsmåden ifølge krav 1, 2 eller 3, hvori R er brom eller iod. 5. Fremgangsmaden ifølge et hvilket som helst af kravene 1-4, hvori forbindelsen med formlen IV reageres med ZnCl2 i nærvær af en palladiumkatalysator, fortrinsvis Pd(PPh3)4. 6. Fremgangsmåden ifølge et hvilket som helst af kravene 1 - 5, hvori den anvendte cyanidforbindelse er NaCN, KCN eller Zn(CN)2. 7. Fremgangsmåden ifølge et hvilket som helst af kravene 1 - 4 og 6, hvori palladiumkatalysatoren er Pd(PPh3)4, Pd2(dba)3 eller Pd(PPh)2Cl2. 8. Fremgangsmåden ifølge krav 7, hvori palladiumkatalysatoren er Pd(PPh3)4. 9. Fremgangsmåden ifølge et hvilket som helst af kravene 1-8, hvori reaktionen udføres i nærvær af en katalytisk mængde af Cu+, fortrinsvis i form af Cul. 10. Fremgangsmåden ifølge et hvilket som helst af kravene 1-8, hvori reaktionen udføres i nærvær af en katalytisk mængde af Zn2+, fortrinsvis som Zn(CN)2.
11. En forbindelse med formlen IV
Figure DK200100060AD00041
hvori R er CF3-(CF2)n-S02-0-, hvori n er et helt tal i området 0-8 eller R er iod. 12. Fremgangsmåden ifølge et hvilket som helst af kravene 1 - 10, hvori forbindelsen med formlen IV er S-enantiomeren. 13. En antidepressiv farmaceutisk komposition omfattende citalopram fremstillet ved processen ifølge et hvilket som helst af kravene 1 -10.
DK200100060A 1999-06-25 2001-01-15 Fremgangsmåde til fremstilling af citalopram DK200100060A (da)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DK200100060A DK200100060A (da) 1999-06-25 2001-01-15 Fremgangsmåde til fremstilling af citalopram

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DKPA199900920 1999-06-25
DK200100060A DK200100060A (da) 1999-06-25 2001-01-15 Fremgangsmåde til fremstilling af citalopram

Publications (1)

Publication Number Publication Date
DK200100060A true DK200100060A (da) 2001-04-10

Family

ID=8099035

Family Applications (2)

Application Number Title Priority Date Filing Date
DK99968622T DK1159274T3 (da) 1999-06-25 1999-11-22 Fremgangsmåde til fremstilling af citalopram
DK200100060A DK200100060A (da) 1999-06-25 2001-01-15 Fremgangsmåde til fremstilling af citalopram

Family Applications Before (1)

Application Number Title Priority Date Filing Date
DK99968622T DK1159274T3 (da) 1999-06-25 1999-11-22 Fremgangsmåde til fremstilling af citalopram

Country Status (36)

Country Link
US (2) US20020077353A1 (da)
EP (1) EP1159274B1 (da)
JP (1) JP3447267B2 (da)
KR (1) KR100491368B1 (da)
CN (2) CN1140521C (da)
AR (1) AR020863A1 (da)
AT (3) AT409961B (da)
AU (2) AU2001100440B4 (da)
BG (1) BG65574B1 (da)
BR (1) BR9917368B1 (da)
CA (2) CA2475401A1 (da)
CH (1) CH691305A5 (da)
CZ (1) CZ292198B6 (da)
DE (2) DE69906389T2 (da)
DK (2) DK1159274T3 (da)
EA (1) EA002560B1 (da)
ES (2) ES2194545T3 (da)
FI (1) FI108641B (da)
GB (2) GB2357761B (da)
HK (1) HK1049002B (da)
HU (1) HUP0103235A3 (da)
IL (2) IL145959A0 (da)
IS (1) IS2343B (da)
IT (1) ITMI991581A1 (da)
MX (1) MXPA01010989A (da)
NO (1) NO328542B1 (da)
NZ (1) NZ514979A (da)
PL (1) PL205579B1 (da)
PT (1) PT1159274E (da)
SE (1) SE516690C2 (da)
SI (1) SI1159274T1 (da)
SK (1) SK285813B6 (da)
TR (1) TR200103702T2 (da)
UA (1) UA63034C2 (da)
WO (1) WO2000013648A2 (da)
ZA (1) ZA200108854B (da)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100454008B1 (ko) 1998-12-23 2004-10-20 하. 룬트벡 아크티에 셀스카브 5-시아노프탈리드의 제조방법
AR022329A1 (es) 1999-01-29 2002-09-04 Lundbeck & Co As H Metodo para la preparacion de 5-cianoftalida
ATE237604T1 (de) 1999-04-14 2003-05-15 Lundbeck & Co As H Verfahren zur herstellung von citalopram
ITMI991579A1 (it) 1999-06-25 2001-01-15 Lundbeck & Co As H Metodo per la preparazione di citalopram
HRP20020344B1 (hr) 1999-10-25 2010-10-31 H. Lundbeck A/S Način priprave citaloprama
CH692298A5 (de) 1999-10-25 2002-04-30 Lundbeck & Co As H Verfahren zur Herstellung von Zwischenstufen für die Citalopramsynthese sowie zur Herstellung von Escitalopram.
AR026063A1 (es) 1999-11-01 2002-12-26 Lundbeck & Co As H Metodo para la preparacion de 5-carboxiftalida.
CN1398263A (zh) 1999-12-28 2003-02-19 H·隆德贝克有限公司 制备西酞普兰的方法
KR100653141B1 (ko) 1999-12-30 2006-12-01 하. 룬트벡 아크티에 셀스카브 시탈로프람의 제조 방법
PL197821B1 (pl) 2000-01-14 2008-04-30 Lundbeck & Co As H Sposób wytwarzania 5-cyjanoftalidu
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.
NL1017500C1 (nl) 2000-03-13 2001-04-26 Lundbeck & Co As H Werkwijze voor de bereiding van Citalopram.
WO2001068629A1 (en) 2000-03-13 2001-09-20 H. Lundbeck A/S Stepwise alkylation of 5-substituted 1-(4-fluorophenyl)-1,3-dihydroisobenzofurans
CN1429219A (zh) 2000-03-13 2003-07-09 H·隆德贝克有限公司 制备西酞普兰的方法
GB2357762B (en) 2000-03-13 2002-01-30 Lundbeck & Co As H Crystalline base of citalopram
HRP20020740A2 (en) 2000-03-14 2004-12-31 Lundbeck & Co As H Method for the preparation of citalopram
NZ521059A (en) * 2000-03-16 2004-04-30 H Method for the preparation of 5-cyano-1-(4-fluorophenyl)-1,3-dihydroisobenzofurans
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
WO2002004435A1 (en) * 2000-07-06 2002-01-17 H. Lundbeck A/S Method for the preparation of citalopram
CA2354877C (en) 2000-08-18 2006-05-02 H. Lundbeck A/S Method for the preparation of citalopram
WO2001045483A2 (en) 2000-12-22 2001-06-28 H. Lundbeck A/S Method for the preparation of pure citalopram
JP2003519121A (ja) * 2000-12-28 2003-06-17 ハー・ルンドベック・アクチエゼルスカベット 純粋なシタロプラムの製造方法
EP1355897A1 (en) 2001-01-30 2003-10-29 Orion Corporation Fermion Process for the preparation of 1-(3-dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile
GB0105627D0 (en) * 2001-03-07 2001-04-25 Cipla Ltd Preparation of phthalanes
JP2005500256A (ja) * 2001-03-09 2005-01-06 ランバクシー ラボラトリーズ リミテッド シタロプラム製造方法
US6967259B2 (en) * 2001-09-24 2005-11-22 Pharmachem Technologies Limited Process for the preparation of Citalopram intermediate
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
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
KR101166280B1 (ko) 2004-08-23 2013-11-27 썬 파마 글로벌 에프제트이 시탈로프램 및 에난티오머의 제조 방법
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
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

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GB8419963D0 (en) * 1984-08-06 1984-09-12 Lundbeck & Co As H Intermediate compound and method
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DK213290D0 (da) * 1990-09-06 1990-09-06 Lundbeck & Co As H Treatment of cerebrovascular disorders
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EP1015416B1 (en) * 1997-07-08 2001-09-19 H. Lundbeck A/S Method for the preparation of citalopram
UA62985C2 (en) * 1997-11-10 2004-01-15 Lunnbeck As H A method for the preparation of citalopram
UA62984C2 (en) * 1997-11-11 2004-01-15 Lunnbeck As H A method for the preparation of citalopram
CN1129592C (zh) * 1998-10-20 2003-12-03 H·隆德贝克有限公司 制备西酞普兰的方法
KR100454008B1 (ko) * 1998-12-23 2004-10-20 하. 룬트벡 아크티에 셀스카브 5-시아노프탈리드의 제조방법
AR022329A1 (es) * 1999-01-29 2002-09-04 Lundbeck & Co As H Metodo para la preparacion de 5-cianoftalida
ATE237604T1 (de) * 1999-04-14 2003-05-15 Lundbeck & Co As H Verfahren zur herstellung von citalopram
ITMI991579A1 (it) * 1999-06-25 2001-01-15 Lundbeck & Co As H Metodo per la preparazione di citalopram
CH692298A5 (de) * 1999-10-25 2002-04-30 Lundbeck & Co As H Verfahren zur Herstellung von Zwischenstufen für die Citalopramsynthese sowie zur Herstellung von Escitalopram.
AR026063A1 (es) * 1999-11-01 2002-12-26 Lundbeck & Co As H Metodo para la preparacion de 5-carboxiftalida.
IES20010143A2 (en) * 2000-02-24 2001-07-25 Lundbeck & Co As H Method for the preparation of citalopram
FR2805812A1 (fr) * 2000-02-24 2001-09-07 Lundbeck & Co As H Procede de preparation du citalopram
CA2354877C (en) * 2000-08-18 2006-05-02 H. Lundbeck A/S Method for the preparation of citalopram
WO2001045483A2 (en) * 2000-12-22 2001-06-28 H. Lundbeck A/S Method for the preparation of pure citalopram
JP2003519121A (ja) * 2000-12-28 2003-06-17 ハー・ルンドベック・アクチエゼルスカベット 純粋なシタロプラムの製造方法

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WO2000013648A2 (en) 2000-03-16
NO328542B1 (no) 2010-03-15
NZ514979A (en) 2004-01-30
ITMI991581A1 (it) 2001-01-15
CH691305A5 (de) 2001-06-29
IS5861A (is) 2001-02-23
PL205579B1 (pl) 2010-05-31
AU1374500A (en) 2000-03-27
SE516690C2 (sv) 2002-02-12
EA200101072A1 (ru) 2002-02-28
EA002560B1 (ru) 2002-06-27
AT409961B (de) 2002-12-27
SI1159274T1 (en) 2003-10-31
HUP0103235A3 (en) 2003-01-28
NO20010319L (no) 2001-02-23
PT1159274E (pt) 2003-08-29
GB0105182D0 (en) 2001-04-18
AU2001100440B4 (en) 2002-01-24
CZ292198B6 (cs) 2003-08-13
GB2357761A (en) 2001-07-04
BR9917368A (pt) 2002-03-05
BR9917368B1 (pt) 2010-02-09
US20090088469A1 (en) 2009-04-02
ZA200108854B (en) 2002-08-28
KR20020012204A (ko) 2002-02-15
IL145959A0 (en) 2002-07-25
SE0100193L (sv) 2001-04-25
FI20010155L (fi) 2001-02-09
CA2290127A1 (en) 2000-12-25
DK1159274T3 (da) 2003-07-21
EP1159274A2 (en) 2001-12-05
CZ2001320A3 (en) 2001-05-16
KR100491368B1 (ko) 2005-05-24
BG106191A (en) 2002-08-30
IS2343B (is) 2008-02-15
AR020863A1 (es) 2002-05-29
HK1049002B (zh) 2004-12-31
ATE235478T1 (de) 2003-04-15
WO2000013648B1 (en) 2001-03-15
US20020077353A1 (en) 2002-06-20
NO20010319D0 (no) 2001-01-19
GB0101504D0 (en) 2001-03-07
GB2357761B (en) 2001-09-05
ITMI991581A0 (it) 1999-07-15
AU2001100440A4 (en) 2001-11-01
HUP0103235A2 (hu) 2002-01-28
HK1049002A1 (en) 2003-04-25
CA2290127C (en) 2005-01-25
MXPA01010989A (es) 2002-06-04
UA63034C2 (en) 2004-01-15
EP1159274B1 (en) 2003-03-26
GB2354239A (en) 2001-03-21
DE69906389T2 (de) 2003-10-30
AT4365U1 (de) 2001-06-25
WO2000013648A8 (en) 2000-05-11
BG65574B1 (bg) 2009-01-30
FI108641B (fi) 2002-02-28
ES2194545T3 (es) 2003-11-16
ATA904199A (de) 2002-05-15
SE0100193D0 (sv) 2001-01-24
JP3447267B2 (ja) 2003-09-16
CN1140521C (zh) 2004-03-03
GB2354239B (en) 2001-06-06
CA2475401A1 (en) 2000-12-25
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TR200103702T2 (tr) 2002-06-21
SK18402001A3 (sk) 2002-06-04
DE69906389D1 (de) 2003-04-30
IL145959A (en) 2007-07-24
DE19983487C1 (de) 2002-07-25
JP2002526386A (ja) 2002-08-20
WO2000013648A3 (en) 2000-07-13
PL346237A1 (en) 2002-01-28
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