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BR9915158A - Método para preparação de citalopram - Google Patents

Método para preparação de citalopram

Info

Publication number
BR9915158A
BR9915158A BR9915158-8A BR9915158A BR9915158A BR 9915158 A BR9915158 A BR 9915158A BR 9915158 A BR9915158 A BR 9915158A BR 9915158 A BR9915158 A BR 9915158A
Authority
BR
Brazil
Prior art keywords
citalopram
alkyl
hydrogen
preparation
treatment
Prior art date
Application number
BR9915158-8A
Other languages
English (en)
Other versions
BR9915158B1 (pt
Inventor
Leone Dall Asta
Hans Petersen
Umberto Casazza
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
Priority claimed from IT002242 external-priority patent/IT1302700B1/it
Priority claimed from IT1999MI001152 external-priority patent/IT1312319B1/it
Priority claimed from IT1999MI001724 external-priority patent/IT1313587B1/it
Application filed by Lundbeck & Co As H filed Critical Lundbeck & Co As H
Publication of BR9915158A publication Critical patent/BR9915158A/pt
Publication of BR9915158B1 publication Critical patent/BR9915158B1/pt

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic 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
    • C07D263/10—Heterocyclic 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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D263/14—Heterocyclic 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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic 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
    • C07D413/04—Heterocyclic 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 directly linked by a ring-member-to-ring-member bond

Landscapes

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

Abstract

<B>"MéTODO PARA PREPARAçãO DE CITALOPRAM"<D> A presente invenção refere-se a um método para a preparação de citalopram ou qualquer de seus enantiómeros e sais com adição de ácido do mesmo, compreendendo o tratamento de um composto de fórmula IV, onde X é O ou S; R^ 1^ - R^ 2^ são, cada um, independentemente selecionados de hidrogênio e C^ 1-6^ alcil, ou R^ 1^ e R^ 2^ juntos formam uma cadeia de C^ 2-5^ alcileno, deste modo formando um anel espiral; R^ 3^ é selecionado de hidrogênio e C^ 1-6^ alcil, R^ 4^ é selecionado de hidrogênio, C^ 1-6^ alcil, um grupo carbóxi ou um grupo precursor do mesmo, ou R^ 3^ e R^ 4^ são selecionados juntos de uma cadeia de C^ 2-5^ alcileno, deste modo formando um anel espiral; com um agente de desidratação ou, alternativamente, onde X e S, clivagem termal do anel de tiazolina ou tratamento com um iniciador radical, a fim de formar o citalopram. A invenção também refere-se a intermediários usado no novo processo para a preparação de citalopram, bem como citalopram preparado de acordo com o novo processo.
BRPI9915158-8A 1998-10-20 1999-10-19 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. BR9915158B1 (pt)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
ITMI98A002242 1998-10-20
IT002242 IT1302700B1 (it) 1998-10-20 1998-10-20 Procedimento per la preparazione di un derivato dell'isobenzofurano
IT1999MI001152 IT1312319B1 (it) 1999-05-25 1999-05-25 Procedimento per la preparazione del citalopram.
ITMI99A001152 1999-05-25
IT1999MI001724 IT1313587B1 (it) 1999-08-02 1999-08-02 Procedimento per la preparazione di un derivato del5-cianoisobenzofurano.
ITMI99A001724 1999-08-02
PCT/DK1999/000576 WO2000023431A1 (en) 1998-10-20 1999-10-19 Method for the preparation of citalopram

Publications (2)

Publication Number Publication Date
BR9915158A true BR9915158A (pt) 2001-08-07
BR9915158B1 BR9915158B1 (pt) 2012-02-22

Family

ID=27274104

Family Applications (1)

Application Number Title Priority Date Filing Date
BRPI9915158-8A BR9915158B1 (pt) 1998-10-20 1999-10-19 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.

Country Status (25)

Country Link
US (1) US6365747B1 (pt)
EP (1) EP1123284B1 (pt)
JP (1) JP3892667B2 (pt)
KR (1) KR100411505B1 (pt)
CN (1) CN1129592C (pt)
AR (1) AR018693A1 (pt)
AT (1) ATE230738T1 (pt)
AU (1) AU746665B2 (pt)
BG (1) BG64704B1 (pt)
BR (1) BR9915158B1 (pt)
CA (1) CA2291134C (pt)
CZ (1) CZ299920B6 (pt)
DE (1) DE69904853T2 (pt)
DK (1) DK1123284T3 (pt)
EA (1) EA002977B1 (pt)
ES (1) ES2189502T3 (pt)
HK (1) HK1042297B (pt)
HU (1) HU228576B1 (pt)
IL (1) IL142346A0 (pt)
IS (1) IS2256B (pt)
NO (1) NO327038B1 (pt)
NZ (1) NZ510858A (pt)
PL (1) PL199423B1 (pt)
SK (1) SK285719B6 (pt)
WO (1) WO2000023431A1 (pt)

Families Citing this family (50)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1140886B1 (en) 1998-12-23 2003-04-02 H. Lundbeck A/S Method for the preparation of 5-cyanophthalide
AR022329A1 (es) 1999-01-29 2002-09-04 Lundbeck & Co As H Metodo para la preparacion de 5-cianoftalida
KR100604156B1 (ko) 1999-04-14 2006-07-25 하. 룬트벡 아크티에 셀스카브 시탈로프람의 제조방법
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
AR021155A1 (es) * 1999-07-08 2002-06-12 Lundbeck & Co As H Tratamiento de desordenes neuroticos
HK1043129B (zh) 1999-10-25 2004-10-21 H‧隆德贝克有限公司 西酞普蘭的製備方法
EP1228056B1 (en) 1999-10-25 2004-09-22 H. Lundbeck A/S Method for the preparation of citalopram
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
HK1052512B (zh) 1999-12-30 2006-03-03 H. 隆德贝克有限公司 西酞普兰的制备方法
PL197821B1 (pl) * 2000-01-14 2008-04-30 Lundbeck & Co As H Sposób wytwarzania 5-cyjanoftalidu
IT1317729B1 (it) * 2000-01-18 2003-07-15 Norpharma S P A Procedimento per la preparazione della 5-carbossiftalide.
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.
GB0005477D0 (en) 2000-03-07 2000-04-26 Resolution Chemicals Limited Process for the preparation of citalopram
NL1017500C1 (nl) 2000-03-13 2001-04-26 Lundbeck & Co As H Werkwijze voor de bereiding van Citalopram.
TR200202166T2 (tr) 2000-03-13 2002-12-23 H. Lndbeck A/S Sitalopramın preparasyon metodu
NZ521204A (en) * 2000-03-13 2004-03-26 H Stepwise alkylation of 5-substituted 1-(4-fluorophenyl)- 1,3-dihydroisobenzofurans for preparing citalopram, an anti depressant
GB2357762B (en) * 2000-03-13 2002-01-30 Lundbeck & Co As H Crystalline base of citalopram
PT1265882E (pt) 2000-03-14 2004-06-30 Lundbeck & Co As H Metodo para preparacao de citalopram; composto e citalopram
HUP0300134A2 (en) * 2000-03-16 2003-05-28 Lundbeck & Co As H Method for the preparation of 5-cyano-1-(4-fluorophenyl)-1,3-dihydroisobenzofurans
US6977306B2 (en) 2000-05-02 2005-12-20 Sumitomo Chemical Company, Limited Citalopram hydrobromide crystal and method for crystallization thereof
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
IL144817A0 (en) 2000-08-18 2002-06-30 Lundbeck & Co As H Method for the preparation of citalopram
IL147226A (en) * 2000-12-22 2006-04-10 Lundbeck & Co As H Process for the preparation of pure citalopram
SK284418B6 (sk) * 2000-12-28 2005-04-01 H. Lundbeck A/S Spôsob výroby citalopramu
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
JP2004527551A (ja) * 2001-05-01 2004-09-09 ハー・ルンドベック・アクチエゼルスカベット エナンチオ純粋なエスシタロプラムの使用方法
WO2003011278A1 (en) 2001-07-31 2003-02-13 H. Lundbeck A/S Crystalline composition containing escitalopram
IS7239A (is) * 2001-12-14 2004-04-29 H. Lundbeck A/S Aðferð til framleiðslu á essítalóprami
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
AU2003207774A1 (en) * 2002-01-30 2003-09-02 Montana State University Pestalotiopsis microsporia isolates and compounds derived therefrom
CA2381341A1 (en) * 2002-04-09 2003-10-09 Torcan Chemical Ltd. Process and intermediates for preparing escitalopram
TWI306846B (en) 2002-08-12 2009-03-01 Lundbeck & Co As H Method for the separation of intermediates which may be used for the preparation of escitalopram
US6812355B2 (en) 2002-10-22 2004-11-02 Sekhsaria Chemicals Limited Process for the manufacture of citalopram hydrobromide from 5-bromophthalide
EP1578738B1 (en) * 2002-12-23 2008-03-12 H. Lundbeck A/S Escitalopram hydrobromide and a method for the preparation thereof
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
CN100569765C (zh) * 2003-12-19 2009-12-16 杭州民生药业集团有限公司 西酞普兰中间体晶体碱
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
ITMI20040717A1 (it) * 2004-04-09 2004-07-09 Adorkem Technology Spa Procedimento chemo-enzimatico per la preparazione dell'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
EP1797060A2 (en) 2004-08-23 2007-06-20 Sun Pharmaceutical Industries Limited "process for preparation of citalopram and enantiomers"
WO2006090409A1 (en) * 2005-02-28 2006-08-31 Kekule Pharma Ltd., An improved process for the preparation of 5 - carboxyphthalide
GB2442619B (en) * 2005-05-04 2010-05-26 Pharmed Medicare Pvt Ltd Chlorination of sucrose acylates using triphosgene
CN101157674B (zh) * 2005-07-12 2010-04-14 西陇化工股份有限公司 西酞普兰盐的提纯方法
US8258291B2 (en) * 2006-10-25 2012-09-04 Mamtek International Limited Process for the preparation of sucralose by the chlorination of sugar with triphosgene (BTC)
WO2009111031A2 (en) * 2008-03-04 2009-09-11 Intra-Cellular Therapies, Inc. Methods of treating vasomotor symptoms
US9346777B2 (en) * 2012-09-06 2016-05-24 MediSynergics, LLC Antiprotozoal compounds
US9284291B2 (en) * 2014-07-29 2016-03-15 MediSynergies, LLC Kappa opioid receptor compounds

Family Cites Families (15)

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Publication number Priority date Publication date Assignee Title
GB1143703A (pt) 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
SK283309B6 (sk) * 1997-07-08 2003-05-02 H. Lundbeck A/S Spôsob výroby citalopramu a medziprodukty
UA62985C2 (en) * 1997-11-10 2004-01-15 Lunnbeck As H A method for the preparation of citalopram
ES2149734T3 (es) * 1997-11-11 2003-02-16 Lundbeck & Co As H Metodo para la preparacion de citalopram.
EP1140886B1 (en) 1998-12-23 2003-04-02 H. Lundbeck A/S Method for the preparation of 5-cyanophthalide
AR022329A1 (es) 1999-01-29 2002-09-04 Lundbeck & Co As H Metodo para la preparacion de 5-cianoftalida
KR100604156B1 (ko) 1999-04-14 2006-07-25 하. 룬트벡 아크티에 셀스카브 시탈로프람의 제조방법
EP1228056B1 (en) 1999-10-25 2004-09-22 H. Lundbeck A/S Method for the preparation of citalopram
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

Also Published As

Publication number Publication date
CN1324351A (zh) 2001-11-28
NO20011936D0 (no) 2001-04-19
BR9915158B1 (pt) 2012-02-22
JP2002527511A (ja) 2002-08-27
ES2189502T3 (es) 2003-07-01
CZ20011418A3 (cs) 2001-10-17
EA200100457A1 (ru) 2001-10-22
EP1123284B1 (en) 2003-01-08
DE69904853D1 (de) 2003-02-13
HK1042297A1 (en) 2002-08-09
HUP0104128A3 (en) 2003-01-28
HUP0104128A2 (hu) 2002-04-29
ATE230738T1 (de) 2003-01-15
NZ510858A (en) 2003-11-28
BG105457A (en) 2001-12-29
DE69904853T2 (de) 2003-09-04
IS2256B (is) 2007-06-15
SK285719B6 (sk) 2007-07-06
CA2291134C (en) 2006-05-23
EA002977B1 (ru) 2002-12-26
KR100411505B1 (ko) 2003-12-18
EP1123284A1 (en) 2001-08-16
AU746665B2 (en) 2002-05-02
KR20010080236A (ko) 2001-08-22
CN1129592C (zh) 2003-12-03
AU6326099A (en) 2000-05-08
PL199423B1 (pl) 2008-09-30
HU228576B1 (en) 2013-04-29
DK1123284T3 (da) 2003-04-28
IS5911A (is) 2001-03-30
AR018693A1 (es) 2001-11-28
BG64704B1 (bg) 2005-12-30
CA2291134A1 (en) 2000-04-20
CZ299920B6 (cs) 2008-12-29
NO20011936L (no) 2001-06-01
HK1042297B (zh) 2004-09-10
NO327038B1 (no) 2009-04-06
US6365747B1 (en) 2002-04-02
IL142346A0 (en) 2002-03-10
JP3892667B2 (ja) 2007-03-14
WO2000023431A1 (en) 2000-04-27
PL347189A1 (en) 2002-03-25
SK5352001A3 (en) 2002-02-05

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Legal Events

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B07A Application suspended after technical examination (opinion) [chapter 7.1 patent gazette]
B09B Patent application refused [chapter 9.2 patent gazette]
B12B Appeal against refusal [chapter 12.2 patent gazette]
B16A Patent or certificate of addition of invention granted [chapter 16.1 patent gazette]

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B21F Lapse acc. art. 78, item iv - on non-payment of the annual fees in time

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B24J Lapse because of non-payment of annual fees (definitively: art 78 iv lpi, resolution 113/2013 art. 12)

Free format text: EM VIRTUDE DA EXTINCAO PUBLICADA NA RPI 2328 DE 18-08-2015 E CONSIDERANDO AUSENCIA DE MANIFESTACAO DENTRO DOS PRAZOS LEGAIS, INFORMO QUE CABE SER MANTIDA A EXTINCAO DA PATENTE E SEUS CERTIFICADOS, CONFORME O DISPOSTO NO ARTIGO 12, DA RESOLUCAO 113/2013.