ES2148120T1 - Metodo para la preparacion de citalopram. - Google Patents

Metodo para la preparacion de citalopram.

Info

Publication number
ES2148120T1
ES2148120T1 ES98905125T ES98905125T ES2148120T1 ES 2148120 T1 ES2148120 T1 ES 2148120T1 ES 98905125 T ES98905125 T ES 98905125T ES 98905125 T ES98905125 T ES 98905125T ES 2148120 T1 ES2148120 T1 ES 2148120T1
Authority
ES
Spain
Prior art keywords
formula
citalopram
defined above
compound
preparation
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.)
Granted
Application number
ES98905125T
Other languages
English (en)
Other versions
ES2148120T3 (es
Inventor
Hans Petersen
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.)
H Lundbeck AS
Original Assignee
H Lundbeck AS
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 AS filed Critical H Lundbeck AS
Publication of ES2148120T1 publication Critical patent/ES2148120T1/es
Application granted granted Critical
Publication of ES2148120T3 publication Critical patent/ES2148120T3/es
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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
    • 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
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/38Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/70Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/84Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/28Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
    • C07C237/30Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to hydrogen atoms or to acyclic carbon atoms
    • 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
    • C07D307/88Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3

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)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pain & Pain Management (AREA)
  • Psychiatry (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Steroid Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Furan Compounds (AREA)

Abstract

Un método para la preparación de citalopram que comprende los pasos de hacer reaccionar un compuesto de Fórmula IV en la cual R 1 es alquilo C1-C6 y X es O o NH, en forma sucesiva con un reactivo de Grignard de 4-halógenofluorofenilo, con lo que se obtiene un compuesto de Fórmula IVa en la cual R 1 y X son como se define anteriormente, y un reactivo de Grignard de 3-halógeno-N,N-dimetilpropilamina, efectuar el cierre de anillo del compuesto resultante de Fórmula V en la cual R 1 y X son como se define anteriormente, y convertir el compuesto resultante de Fórmula VI donde R 1 y X son como se define anteriormente, en el correspondiente derivado 5-ciano, es decir citalopram, el cual se aísla como la base o como una de sus sales farmacéuticamente aceptables.
ES98905125T 1997-07-08 1998-03-03 Metodo para la preparacion de citalopram. Expired - Lifetime ES2148120T3 (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US5278897P 1997-07-08 1997-07-08
DK82697 1997-07-08

Publications (2)

Publication Number Publication Date
ES2148120T1 true ES2148120T1 (es) 2000-10-16
ES2148120T3 ES2148120T3 (es) 2002-01-16

Family

ID=26064729

Family Applications (1)

Application Number Title Priority Date Filing Date
ES98905125T Expired - Lifetime ES2148120T3 (es) 1997-07-08 1998-03-03 Metodo para la preparacion de citalopram.

Country Status (23)

Country Link
US (1) US6229026B1 (es)
EP (1) EP1015416B1 (es)
JP (1) JP3526581B2 (es)
KR (1) KR100357975B1 (es)
CN (1) CN1206207C (es)
AT (1) ATE205824T1 (es)
AU (1) AU737610B2 (es)
BG (1) BG64823B1 (es)
CA (1) CA2291067C (es)
CZ (1) CZ291440B6 (es)
DE (2) DE69801764T2 (es)
DK (1) DK1015416T3 (es)
EA (1) EA001728B1 (es)
ES (1) ES2148120T3 (es)
HU (1) HU228744B1 (es)
IL (2) IL133511A (es)
IS (1) IS2023B (es)
NO (1) NO322146B1 (es)
NZ (1) NZ501737A (es)
PT (1) PT1015416E (es)
SK (1) SK283309B6 (es)
TR (1) TR200000066T2 (es)
WO (1) WO1998019513A2 (es)

Families Citing this family (52)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
UA62985C2 (en) 1997-11-10 2004-01-15 Lunnbeck As H A method for the preparation of citalopram
PL199423B1 (pl) * 1998-10-20 2008-09-30 Lundbeck & Co As H Sposób wytwarzania citalopramu
CN1149208C (zh) 1998-12-23 2004-05-12 H.隆德贝克有限公司 制备5-氰基2-苯并[c]呋喃酮的方法
AR022329A1 (es) 1999-01-29 2002-09-04 Lundbeck & Co As H Metodo para la preparacion de 5-cianoftalida
NZ514671A (en) * 1999-04-14 2003-10-31 H Method for the preparation of citalopram
US6245782B1 (en) 1999-05-17 2001-06-12 Heartdrug Research L.L.C. Methods of inhibiting platelet activation with selective serotonin reuptake inhibitors
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
ITMI991486A1 (it) * 1999-07-06 2001-01-06 Vis Farmaceutici S P A Processo per la sintesi di citalopram
EP1298124B1 (en) 1999-10-25 2007-02-28 H. Lundbeck A/S Method For the Preparation of 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.
EA004742B1 (ru) 1999-12-28 2004-08-26 Х.Лундбекк А/С Способ получения циталопрама
WO2001049672A1 (en) * 1999-12-30 2001-07-12 H. Lundbeck A/S Method for the preparation of citalopram
TR200201783T2 (tr) 2000-01-14 2002-12-23 H. Lundbeck A/S 5-Siyanofatalid hazırlamak için yöntem
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
GB2357762B (en) 2000-03-13 2002-01-30 Lundbeck & Co As H Crystalline base of citalopram
NL1017500C1 (nl) 2000-03-13 2001-04-26 Lundbeck & Co As H Werkwijze voor de bereiding van Citalopram.
CZ20023100A3 (cs) * 2000-03-13 2003-02-12 H. Lundbeck A/S Způsob výroby citalopramu
KR20020080481A (ko) 2000-03-13 2002-10-23 하. 룬트벡 아크티에 셀스카브 시탈로프람의 제조 방법
SK14512002A3 (sk) 2000-03-14 2003-03-04 H. Lundbeck A/S Spôsob výroby citalopramu, medziprodukt a citalopram výrobený týmto spôsobom
EP1274699A1 (en) * 2000-03-16 2003-01-15 H. Lundbeck A/S 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
IL144817A0 (en) * 2000-08-18 2002-06-30 Lundbeck & Co As H Method for the preparation of citalopram
IT1319686B1 (it) * 2000-12-12 2003-10-23 C D Farmasint S R L Procedimento di preparazione di citalopram.
JP3798982B2 (ja) 2000-12-22 2006-07-19 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
CA2359810C (en) 2000-12-28 2002-11-05 H. Lundbeck A/S Process for the preparation of pure citalopram
DE10112828C1 (de) * 2000-12-28 2002-11-21 Lundbeck & Co As H Verfahren zur Herstellung von Citalopram
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
BG65271B1 (bg) * 2001-06-18 2007-11-30 H. Lundbeck A/S Метод за получаване на циталопрам
IN192057B (es) * 2001-07-19 2004-02-14 Ranbaxy Lab Ltd
HRP20031073A2 (en) 2001-07-31 2004-04-30 Lundbeck & Co As H Crystalline composition containing escitalopram
PT1281707E (pt) * 2001-08-02 2005-04-29 Infosint Sa Processo para a preparacao de isobenzofuranos 5-substituidos
GR1004635B (el) * 2001-08-14 2004-07-14 H@Αlundbeckαa@Sαα Μεθοδοσαπαρασκευησατησασιταλοπραμης@αα
EP1288211A1 (en) * 2001-08-28 2003-03-05 Sekhsaria Chemicals Ltd. Improved process for the manufacture of citalopram hydrobromide from 5-bromophthalide
WO2003057132A2 (en) 2002-01-07 2003-07-17 Sun Pharmaceutical Industries Limited Process for the preparation of 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)- 1,3-dihydro-5-isobenzofuran carbonitrile
GB2387844B (en) * 2002-02-27 2005-05-11 Matrix Lab Ltd Separation of impurities from a crude mixture of citalopram
HU0200980D0 (es) * 2002-03-14 2002-05-29 Gabor S Pal Dr
BG65515B1 (bg) * 2002-07-26 2008-10-31 H. Lundbeck A/S Метод за получаване на 5-цианофталид
AU2002330730A1 (en) * 2002-08-14 2004-03-03 Natco Pharma Limited Process for the preparation of high purity citalopram and its pharmaceutically acceptable salts
US6812355B2 (en) 2002-10-22 2004-11-02 Sekhsaria Chemicals Limited Process for the manufacture of citalopram hydrobromide from 5-bromophthalide
ITMI20030479A1 (it) * 2003-03-13 2004-09-14 Adorkem Technology S P A Procedimento per la preparazione di un ciano-isobenzofurano.
CN101362743A (zh) * 2003-03-21 2009-02-11 H.隆德贝克有限公司 用于制备西酞普兰和依他普仑的中间体
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
DE60300502T2 (de) * 2003-10-28 2006-02-23 Adorkem Technology S.P.A., Costa Volpino Verfahren zur Herstellung von Citalopram
KR101166280B1 (ko) 2004-08-23 2013-11-27 썬 파마 글로벌 에프제트이 시탈로프램 및 에난티오머의 제조 방법
TWI347942B (en) 2005-06-22 2011-09-01 Lundbeck & Co As H Crystalline base of escitalopram and orodispersible tablets comprising escitalopram base
US7834201B2 (en) 2005-06-22 2010-11-16 H. Lundbeck A/S Crystalline base of escitalopram and orodispersible tablets comprising escitalopram base
WO2009111031A2 (en) * 2008-03-04 2009-09-11 Intra-Cellular Therapies, Inc. Methods of treating vasomotor symptoms

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1143703A (es) 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
DK213290D0 (da) * 1990-09-06 1990-09-06 Lundbeck & Co As H Treatment of cerebrovascular disorders
NZ243065A (en) 1991-06-13 1995-07-26 Lundbeck & Co As H Piperidine derivatives and pharmaceutical compositions

Also Published As

Publication number Publication date
CZ291440B6 (cs) 2003-03-12
US6229026B1 (en) 2001-05-08
IS5300A (is) 1999-12-14
NZ501737A (en) 2001-10-26
ATE205824T1 (de) 2001-10-15
IL133511A0 (en) 2001-04-30
CN1206207C (zh) 2005-06-15
NO20000008L (no) 2000-01-03
EA001728B1 (ru) 2001-08-27
NO20000008D0 (no) 2000-01-03
IL153125A (en) 2008-11-03
SK32000A3 (en) 2000-07-11
KR20010021516A (ko) 2001-03-15
ES2148120T3 (es) 2002-01-16
BG104116A (en) 2000-12-29
EA200000102A1 (ru) 2000-06-26
AU737610B2 (en) 2001-08-23
CN1495157A (zh) 2004-05-12
DK1015416T3 (da) 2001-11-05
HUP0003177A3 (en) 2002-12-28
AU6609898A (en) 1998-05-29
NO322146B1 (no) 2006-08-21
HUP0003177A2 (hu) 2001-04-28
IS2023B (is) 2005-08-15
BG64823B1 (bg) 2006-05-31
PT1015416E (pt) 2002-03-28
DE1015416T1 (de) 2000-10-05
KR100357975B1 (ko) 2002-10-25
WO1998019513A2 (en) 1998-05-14
EP1015416A2 (en) 2000-07-05
HU228744B1 (en) 2013-05-28
WO1998019513A3 (en) 2000-05-04
DE69801764T2 (de) 2002-07-04
JP3526581B2 (ja) 2004-05-17
DE69801764D1 (de) 2001-10-25
IL133511A (en) 2004-05-12
CA2291067C (en) 2002-07-30
SK283309B6 (sk) 2003-05-02
CA2291067A1 (en) 1998-05-14
TR200000066T2 (tr) 2000-11-21
JP2002509526A (ja) 2002-03-26
EP1015416B1 (en) 2001-09-19
CZ200062A3 (cs) 2000-07-12

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