ZA200110179B - Process for the preparation of pure citalopram. - Google Patents

Process for the preparation of pure citalopram.

Info

Publication number: ZA200110179B
Authority: ZA; South Africa
Prior art keywords: preparation; pure citalopram; citalopram; pure
Prior art date: 2000-12-22

Application number

ZA200110179A

Other languages

English (en)

Inventor

Marco Villa

Federico Sbrogio

Robert Dancer

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.)

2000-12-22

Filing date

2001-12-11

Publication date

2002-12-11

2001-12-11 Application filed by Lundbeck & Co As H filed Critical Lundbeck & Co As H

2002-12-11 Publication of ZA200110179B publication Critical patent/ZA200110179B/xx

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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Psychiatry (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Pain & Pain Management (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

ZA200110179A 2000-12-22 2001-12-11 Process for the preparation of pure citalopram. ZA200110179B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DKPA200001929		2000-12-22

Publications (1)

Publication Number	Publication Date
ZA200110179B true ZA200110179B (en)	2002-12-11

Family

ID=8159922

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200110179A ZA200110179B (en)	2000-12-22	2001-12-11	Process for the preparation of pure citalopram.

Country Status (43)

Country	Link
US (1)	US6455710B1 (de)
EP (2)	EP1462447A3 (de)
JP (1)	JP3798982B2 (de)
KR (1)	KR100439329B1 (de)
CN (1)	CN1282648C (de)
AR (1)	AR030056A1 (de)
AT (2)	ATE277920T1 (de)
AU (2)	AU2001100405B4 (de)
BE (2)	BE1013212A6 (de)
BG (1)	BG65131B1 (de)
BR (1)	BR0106272A (de)
CA (1)	CA2360303C (de)
CH (1)	CH691535A5 (de)
CZ (1)	CZ292200B6 (de)
DE (2)	DE60105926T2 (de)
DK (1)	DK1181713T3 (de)
EA (1)	EA003581B1 (de)
ES (2)	ES2228824T3 (de)
FI (2)	FI108639B (de)
FR (1)	FR2812877B1 (de)
GB (1)	GB2357763B (de)
GR (1)	GR1003874B (de)
HK (1)	HK1048812B (de)
HR (1)	HRP20020004A2 (de)
HU (2)	HU0101029D0 (de)
IE (1)	IES20010254A2 (de)
IL (1)	IL147226A (de)
IS (1)	IS2060B (de)
IT (1)	ITMI20010602A1 (de)
MX (1)	MXPA01013151A (de)
NL (2)	NL1017525C1 (de)
NO (1)	NO20011271A (de)
NZ (1)	NZ516298A (de)
PL (1)	PL205724B1 (de)
PT (1)	PT1181713E (de)
SE (1)	SE517623C2 (de)
SG (1)	SG167655A1 (de)
SI (1)	SI1181713T1 (de)
SK (2)	SK284428B6 (de)
TR (1)	TR200201166T1 (de)
UA (1)	UA71634C2 (de)
WO (1)	WO2001045483A2 (de)
ZA (1)	ZA200110179B (de)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
ITMI991581A1 (it) *	1999-06-25	2001-01-15	Lundbeck & Co As H	Metodo per la preparazione di citalopram
GB2360281B (en)	1999-10-25	2002-01-16	Lundbeck & Co As H	Method for the preparation of citalopram
WO2001047909A1 (en)	1999-12-28	2001-07-05	H. Lundbeck A/S	Method for the preparation of citalopram
PL198803B1 (pl)	1999-12-30	2008-07-31	Lundbeck & Co As H	Sposób wytwarzania 5-cyjano-3H-izobenzofuran-1-onu
ES2206177T3 (es)	2000-01-14	2004-05-16	H. Lundbeck A/S	Metodo para la preparacion de 5-cianoftalida.
IES20010157A2 (en)	2000-03-03	2002-03-06	Lundbeck & Co As H	Method for the preparation of citalopram
CA2402553A1 (en)	2000-03-13	2001-09-20	H. Lundbeck A/S	Stepwise alkylation of 5-substituted 1-(4-fluorophenyl)-1,3-dihydroisobenzofurans
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
IL151488A0 (en)	2000-03-14	2003-04-10	Lundbeck & Co As H	Method for the preparation of citalopram
EP1274699A1 (de) *	2000-03-16	2003-01-15	H. Lundbeck A/S	Verfahren zur herstellung von 5-cyano-1-(4-fluorophenyl)-1,3-dihydroisobenzofuranen
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
CA2354880C (en)	2000-08-18	2003-06-03	H. Lundbeck A/S	Method for the preparation of citalopram
PT1181272E (pt)	2000-12-28	2003-01-31	Lundbeck & Co As H	Processo para a preparacao de citalopram puro
GB0105627D0 (en) *	2001-03-07	2001-04-25	Cipla Ltd	Preparation of phthalanes
RU2003130073A (ru) *	2001-03-09	2005-04-10	Ранбакси Лабораторис Лимитед (In)	Способ получения циталопрама
US6967259B2 (en) *	2001-09-24	2005-11-22	Pharmachem Technologies Limited	Process for the preparation of Citalopram intermediate
MXPA04004368A (es) *	2001-11-08	2004-08-11	Sepracor Inc	Metodos para tratar depresion y otros transtornos del sistema nervioso central utilizando desmetil-y didesmetil-metabolitos del citalopram enantiomericamente enriquecidos.
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
GB0204607D0 (en) *	2002-02-27	2002-04-10	Matrix Lab Ltd	Process
BR0316217B1 (pt) *	2002-11-15	2013-10-01		tratamento de purificaÇço/descoloraÇço para nitrilas graxas
US20050154052A1 (en) *	2003-03-24	2005-07-14	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
CA2546422A1 (en) *	2003-10-28	2005-05-12	Wockhardt Limited	Improved process for the manufacture of citalopram hydrobromide
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
TWI347942B (en) *	2005-06-22	2011-09-01	Lundbeck & Co As H	Crystalline base of escitalopram and orodispersible tablets comprising escitalopram base
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 (32)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE536169C (de) *	1926-08-21	1931-10-20	British Dyestuffs Corp Ltd	Verfahren zur Gewinnung von tertiaeren aromatischen Aminen aus ihren Gemischen mit sekundaeren und primaeren aromatischen Aminen
US1992111A (en) *	1931-06-20	1935-02-19	Du Pont	Separation of secondary and tertiary amines
DE1032261B (de) *	1955-03-08	1958-06-19	Leda Chemicals Ltd	Verfahren zur Abtrennung sekundaerer Amine aus einer primaeres und sekundaeres Amin enthaltenden Mischung
GB1143702A (de)	1965-03-18
GB1526331A (en) *	1976-01-14	1978-09-27	Kefalas As	Phthalanes
US4302399A (en) *	1978-09-28	1981-11-24	Dynapol	Acetylation of crude reaction products containing polymeric colorants
GB8419963D0 (en)	1984-08-06	1984-09-12	Lundbeck & Co As H	Intermediate compound and method
US4943591A (en)	1984-10-17	1990-07-24	Glaxo Group Limited	Dichloroaniline derivatives
DE3926765A1 (de) *	1989-08-12	1991-02-14	Hoechst Ag	Verfahren zur verminderung von primaerem und sekundaerem amin in einem tertiaeren amin
US5296507A (en)	1990-09-06	1994-03-22	H.Lundbeck A/S	Treatment of cerbrovascular disorders
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
EP0993524B1 (de) *	1997-06-30	2002-11-20	Beloit Technologies, Inc.	Verfahren und vorrichtung zum auftragen einer beschichtung auf eine bei hoher geschwindigkeit laufende papierbahn
JP3526581B2 (ja)	1997-07-08	2004-05-17	ハー・ルンドベック・アクティーゼルスカブ	シタロプラムの製造方法
UA62985C2 (en)	1997-11-10	2004-01-15	Lunnbeck As H	A method for the preparation of citalopram
CZ292911B6 (cs)	1997-11-11	2004-01-14	H. Lundbeck A/S	Způsob výroby citalopramu
PL199423B1 (pl) *	1998-10-20	2008-09-30	Lundbeck & Co As H	Sposób wytwarzania citalopramu
TR200101796T2 (tr)	1998-12-23	2001-11-21	H. Lundbeck A/S	5-Siyanofitalitin preparasyonuna yönelik metot
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
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
GB2360281B (en)	1999-10-25	2002-01-16	Lundbeck & Co As H	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
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
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
CA2354880C (en)	2000-08-18	2003-06-03	H. Lundbeck A/S	Method for the preparation of citalopram
PT1181272E (pt)	2000-12-28	2003-01-31	Lundbeck & Co As H	Processo para a preparacao de citalopram puro

2001
- 2001-03-07 IL IL147226A patent/IL147226A/en not_active IP Right Cessation
- 2001-03-07 BR BR0106272-7A patent/BR0106272A/pt not_active Application Discontinuation
- 2001-03-07 SK SK1848-2001A patent/SK284428B6/sk not_active IP Right Cessation
- 2001-03-07 AU AU2001100405A patent/AU2001100405B4/en not_active Ceased
- 2001-03-07 EA EA200200018A patent/EA003581B1/ru not_active IP Right Cessation
- 2001-03-07 CN CNB018011225A patent/CN1282648C/zh not_active Expired - Lifetime
- 2001-03-07 KR KR10-2001-7016686A patent/KR100439329B1/ko not_active IP Right Cessation
- 2001-03-07 EP EP04004482A patent/EP1462447A3/de not_active Withdrawn
- 2001-03-07 AT AT01913726T patent/ATE277920T1/de not_active IP Right Cessation
- 2001-03-07 DK DK01913726T patent/DK1181713T3/da active
- 2001-03-07 TR TR2002/01166T patent/TR200201166T1/xx unknown
- 2001-03-07 NL NL1017525A patent/NL1017525C1/nl not_active IP Right Cessation
- 2001-03-07 ES ES01913726T patent/ES2228824T3/es not_active Expired - Lifetime
- 2001-03-07 CA CA002360303A patent/CA2360303C/en not_active Expired - Fee Related
- 2001-03-07 MX MXPA01013151A patent/MXPA01013151A/es active IP Right Grant
- 2001-03-07 EP EP01913726A patent/EP1181713B1/de not_active Expired - Lifetime
- 2001-03-07 SK SK4-2005A patent/SK286283B6/sk not_active IP Right Cessation
- 2001-03-07 WO PCT/DK2001/000147 patent/WO2001045483A2/en active Application Filing
- 2001-03-07 SG SG200504030-8A patent/SG167655A1/en unknown
- 2001-03-07 JP JP2001546230A patent/JP3798982B2/ja not_active Expired - Fee Related
- 2001-03-07 AU AU39201/01A patent/AU3920101A/en active Pending
- 2001-03-07 PT PT01913726T patent/PT1181713E/pt unknown
- 2001-03-07 SI SI200130238T patent/SI1181713T1/xx unknown
- 2001-03-07 PL PL353398A patent/PL205724B1/pl not_active IP Right Cessation
- 2001-03-07 DE DE60105926T patent/DE60105926T2/de not_active Expired - Lifetime
- 2001-03-09 IS IS5883A patent/IS2060B/xx unknown
- 2001-03-09 HU HU0101029A patent/HU0101029D0/hu unknown
- 2001-03-12 GB GB0105983A patent/GB2357763B/en not_active Revoked
- 2001-03-12 CZ CZ2001890A patent/CZ292200B6/cs not_active IP Right Cessation
- 2001-03-13 NO NO20011271A patent/NO20011271A/no not_active IP Right Cessation
- 2001-03-13 FI FI20010500A patent/FI108639B/fi not_active IP Right Cessation
- 2001-03-14 FR FR0103455A patent/FR2812877B1/fr not_active Expired - Fee Related
- 2001-03-15 AR ARP010101209A patent/AR030056A1/es not_active Application Discontinuation
- 2001-03-15 IE IE20010254A patent/IES20010254A2/en not_active IP Right Cessation
- 2001-03-16 DE DE10112829A patent/DE10112829C1/de not_active Expired - Fee Related
- 2001-03-16 GR GR20010100132A patent/GR1003874B/el not_active IP Right Cessation
- 2001-03-21 AT AT0020801U patent/AT4367U1/de not_active IP Right Cessation
- 2001-03-22 BE BE2001/0188A patent/BE1013212A6/fr not_active IP Right Cessation
- 2001-03-22 IT IT2001MI000602A patent/ITMI20010602A1/it unknown
- 2001-03-22 CH CH00545/01A patent/CH691535A5/de not_active IP Right Cessation
- 2001-06-22 NL NL1018360A patent/NL1018360C1/nl not_active IP Right Cessation
- 2001-06-26 BE BE2001/0435A patent/BE1013213A6/fr not_active IP Right Cessation
- 2001-07-03 UA UA2002021552A patent/UA71634C2/uk unknown
- 2001-07-05 HU HU0102817A patent/HUP0102817A3/hu unknown
- 2001-07-26 FI FI20011577A patent/FI20011577A0/fi unknown
- 2001-07-27 ES ES200101762A patent/ES2170732B2/es not_active Expired - Fee Related
- 2001-09-14 SE SE0103045A patent/SE517623C2/sv not_active IP Right Cessation
- 2001-12-10 BG BG106203A patent/BG65131B1/bg unknown
- 2001-12-11 ZA ZA200110179A patent/ZA200110179B/xx unknown
- 2001-12-20 NZ NZ516298A patent/NZ516298A/xx unknown
2002
- 2002-01-04 HR HR20020004A patent/HRP20020004A2/hr not_active Application Discontinuation
- 2002-01-08 US US10/046,126 patent/US6455710B1/en not_active Expired - Fee Related
2003
- 2003-02-10 HK HK03100966.7A patent/HK1048812B/zh not_active IP Right Cessation

Also Published As

Publication number	Publication date
SK286283B6 (sk)	2008-06-06
ES2170732B2 (es)	2003-09-16
BG65131B1 (bg)	2007-03-30
SI1181713T1 (en)	2005-02-28
CA2360303A1 (en)	2001-06-28
CZ292200B6 (cs)	2003-08-13
SG167655A1 (en)	2011-01-28
FI20011577A0 (fi)	2001-07-26
AT4367U1 (de)	2001-06-25
BG106203A (en)	2002-08-30
BE1013213A6 (fr)	2001-10-02
SK284428B6 (sk)	2005-04-01
GR1003874B (el)	2002-04-24
HUP0102817A3 (en)	2003-07-28
PL205724B1 (pl)	2010-05-31
EP1462447A3 (de)	2004-11-17
KR100439329B1 (ko)	2004-07-07
BE1013212A6 (fr)	2001-10-02
HU0102817D0 (en)	2001-09-28
GB0105983D0 (en)	2001-05-02
NL1017525C1 (nl)	2001-04-26
ATE277920T1 (de)	2004-10-15
CN1366525A (zh)	2002-08-28
NZ516298A (en)	2002-12-20
AU3920101A (en)	2001-07-03
IL147226A0 (en)	2002-08-14
SE0103045L (sv)	2002-06-23
HK1048812B (zh)	2007-06-01
ES2228824T3 (es)	2005-04-16
WO2001045483A3 (en)	2001-12-27
AU2001100405B4 (en)	2002-03-21
IS2060B (is)	2005-11-15
SK18482001A3 (sk)	2002-05-09
HRP20020004A2 (en)	2003-04-30
US6455710B1 (en)	2002-09-24
HU0101029D0 (en)	2001-05-28
US20020120005A1 (en)	2002-08-29
GB2357763A (en)	2001-07-04
SE517623C2 (sv)	2002-06-25
EA003581B1 (ru)	2003-06-26
IES20010254A2 (en)	2002-03-06
NO312462B1 (no)	2002-05-13
FR2812877A1 (fr)	2002-02-15
SE0103045D0 (sv)	2001-09-14
EP1462447A2 (de)	2004-09-29
FR2812877B1 (fr)	2003-04-04
DE60105926T2 (de)	2005-11-24
TR200201166T1 (tr)	2002-10-21
DK1181713T3 (da)	2005-01-31
AR030056A1 (es)	2003-08-13
KR20020065345A (ko)	2002-08-13
HK1048812A1 (en)	2003-04-17
CA2360303C (en)	2003-08-12
MXPA01013151A (es)	2002-08-12
ITMI20010602A0 (it)	2001-03-22
DE10112829C1 (de)	2002-07-25
EA200200018A1 (ru)	2002-04-25
EP1181713A2 (de)	2002-02-27
NO20011271A (no)	2002-05-13
WO2001045483A2 (en)	2001-06-28
PL353398A1 (en)	2003-11-17
PT1181713E (pt)	2005-02-28
DE60105926D1 (de)	2004-11-04
IL147226A (en)	2006-04-10
FI108639B (fi)	2002-02-28
CH691535A5 (de)	2001-08-15
GB2357763B (en)	2002-01-16
JP2003517484A (ja)	2003-05-27
FI20010500A0 (fi)	2001-03-13
BR0106272A (pt)	2004-06-15
HUP0102817A2 (hu)	2001-12-28
ES2170732A1 (es)	2002-08-01
JP3798982B2 (ja)	2006-07-19
CZ2001890A3 (cs)	2002-08-14
AU2001100405A4 (en)	2001-11-01
IS5883A (is)	2001-06-20
UA71634C2 (uk)	2004-12-15
NO20011271D0 (no)	2001-03-13
NL1018360C1 (nl)	2001-10-04
EP1181713B1 (de)	2004-09-29
ITMI20010602A1 (it)	2002-09-22
CN1282648C (zh)	2006-11-01

Publication	Publication Date	Title
ZA200110179B (en)	2002-12-11	Process for the preparation of pure citalopram.
GB2356199B (en)	2001-10-03	Process for the preparation of pure citalopram
HU0103291D0 (en)	2001-10-28	Process for the preparation of citalopram
ZA200206699B (en)	2003-11-21	Method for the preparation of citalopram.
IL151059A0 (en)	2003-04-10	Method for the preparation of citalopram
IL161026A0 (en)	2004-08-31	Process for the preparation of citalopram
MXPA03001800A (es)	2003-06-24	Proceso para la preparacion de fenilacetonitrilos sustituidos.
IL151467A0 (en)	2003-04-10	Method for the preparation of citalopram
HK1056171A1 (en)	2004-02-06	Method for the preparation of citalopram
HK1040984A1 (zh)	2002-06-28	製備d，l-薄荷醇的方法
IL148525A0 (en)	2002-09-12	Method for the preparation of citalopram
IL151489A0 (en)	2003-04-10	Method for the preparation of citalopram
IL137364A (en)	2005-08-31	Process for the preparation of 6,6-dimethylhept-1-en-4-yn-3-ol
MXPA03005933A (es)	2003-09-10	Proceso para la fabricacion de formulaciones solidas.
GB2359811B (en)	2003-03-05	Process for the preparation of pure citalopram
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