DK200100959A - Fremgangsmåde til fremstilling af citalopram - Google Patents
Fremgangsmåde til fremstilling af citalopram Download PDFInfo
- Publication number
- DK200100959A DK200100959A DK200100959A DKPA200100959A DK200100959A DK 200100959 A DK200100959 A DK 200100959A DK 200100959 A DK200100959 A DK 200100959A DK PA200100959 A DKPA200100959 A DK PA200100959A DK 200100959 A DK200100959 A DK 200100959A
- Authority
- DK
- Denmark
- Prior art keywords
- formula
- propyl magnesium
- preparation
- citalopram
- dimethylamino
- Prior art date
Links
- 0 *OCc1cc(C#N)ccc1C(c(cc1)ccc1F)=O Chemical compound *OCc1cc(C#N)ccc1C(c(cc1)ccc1F)=O 0.000 description 1
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
-
- 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)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
KRAV
1. En fremgangsmåde til fremstilling af citalopram omfattende reaktion af en forbindelse med formlen IV
hvori R er C,.6 alkyl, acyl, Cu alkylsulfonyl eller arylsulfonyl, roed 3-(N,N-dimethyIarmiio)-propylmagnesiumhalid, fortrinsvis 3-(N,N-dimethylamirto)propylniagiicsiuinchlorid for at opnå citalopram
som isoleres som basen eller et farmaceutisk acceptabelt salt deraf. 1. Fremgangsmåden ifølge krav 1 kendetegnet ved, at mellemproduktet med formlen IV fremstilles ved oxidation af den tilsvarende forbindelse med formlen V:
hvori R er defineret som i krav 1.
3. Fremgangsmåden ifølge krav 2 kendetegnet ved, at forbindelsen med formlen V fremstilles ved beskyttelse af hydroxymetbylalkoholen af (4-cyano-2-hydroxymethylphenylX4-fluoiphenyl)methanol af formel VI
4. Fremgangsmåden ifølge krav 1 kendetegnet ved, at mellemproduktet med formlen IV fremstilles ved oxidadv spaltning af den tilsvarende forbindelse med formlen VH:
hvori R er som defineret som i krav 1. 5. Fremgangsmåden ifølge krav 4 kendetegnet ved at den oxidative spaltning af forbindelen med formlen VII sker ved oxidation fortrinsvis med af MnOf (permanganater), eller ozon, RuClj, OsO«. 6. Fremgangsmåden ifølge et hvilket som helst af kravene 4 - 5 kendetegnet ved, at mellemproduktalkenen med fonnlen ΥΠ fremstilles ved beskyttelse og dehydrering af den tilsvarende forbindelse med formlen ΙΠ:
hvori forbindelsen med formlen III er R-enantiomcren. 7. Fremgangsmåden ifølge krav I kendetegnet ved, at mellemproduktet roed formlen IV fremstilles ved reaktion af 5-cyanophthalid med 4-fluorphenylmagnesiumhalid, fortrinsvis 4-iluorphenylmagnesiumbromid efterfulgt af reaktion med R-X for at fremstille kctonforbindelsen med formlen IV, hvori R er som defineret i krav 1 og X er en leavjng-grnppe, fortrinsvis er R-X pivaloylchlorid, 3,5-dimethoxybenzoylcWorid, methyliodid, cthylbromid, tosylchlorid, Me2S04 eller MeS02Cl. 8. Fremgangsmåde til fremstilling af den racemiske forbindelse med formlen III omfattende de følgende trin
a) afbeskyttelse af en forbindelse med formlen IV
hvori R er som defineret i krav 1
b) reaktion af den opnåede forbindelse med formlen VIII
med 3-(N,N-dimefoylamino)propylmagnesiuinhaUd, fortrinsvis 3-(N,N-dimethyI-amino)propylmagnesiumchlorid, for at fremstille den racemiske forbindelse med formlen m
9. Fremgangsmåden ifølge et hvilket som helst af kravene 1-8 hvori R er acyl, fortrinsvis pivaloyl, acetyl eller eventuelt substitueret benzoyt. JO. En forbindelse med formlen IV:
hvori R er C,.« alkyl, acyl, CM alkylsulfonyl eller arylsulfonyl, fortrinsvis pivaloyl, acetyl eller eventuelt substitueret benzoyl. 11. En antidepressiv farmaceutisk komposition omfattende citalopram fremstillet ved fremgangsmåden ifølge et hvilket om helst af kravene 1-9. 12. Anvendelse af et mellemprodukt ifølge krav 10 til fremstilling af citalopram eller S-citalopram.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK200100959A DK200100959A (da) | 1999-10-25 | 2001-06-20 | Fremgangsmåde til fremstilling af citalopram |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH02004/01A CH692298A5 (de) | 1999-10-25 | 1999-10-25 | Verfahren zur Herstellung von Zwischenstufen für die Citalopramsynthese sowie zur Herstellung von Escitalopram. |
| ES200150056A ES2169709A1 (es) | 1999-10-25 | 1999-10-25 | Metodo para la preparacion de citalopram |
| PCT/DK1999/000581 WO2000012044A2 (en) | 1999-10-25 | 1999-10-25 | Method for the preparation of citalopram |
| CH01179/01A CH692421A5 (de) | 1999-10-25 | 1999-10-25 | Verfahren zur Herstellung von Citalopram. |
| DK200100959A DK200100959A (da) | 1999-10-25 | 2001-06-20 | Fremgangsmåde til fremstilling af citalopram |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK200100959A true DK200100959A (da) | 2001-07-11 |
Family
ID=27429871
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK200100959A DK200100959A (da) | 1999-10-25 | 2001-06-20 | Fremgangsmåde til fremstilling af citalopram |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6407267B1 (da) |
| EP (1) | EP1228056B1 (da) |
| AU (1) | AU742554B2 (da) |
| CH (2) | CH692298A5 (da) |
| DK (1) | DK200100959A (da) |
| ES (2) | ES2169709A1 (da) |
| GB (1) | GB2360281B (da) |
| NO (1) | NO325185B1 (da) |
| SK (1) | SK287139B6 (da) |
| TR (1) | TR200101874T1 (da) |
| WO (1) | WO2000012044A2 (da) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA002977B1 (ru) | 1998-10-20 | 2002-12-26 | Х.Лундбекк А/С | Способ получения циталопрама |
| PT1140886E (pt) | 1998-12-23 | 2003-08-29 | Lundbeck & Co As H | Metodo para a preparacao de 5- cianoftalida |
| AR022329A1 (es) | 1999-01-29 | 2002-09-04 | Lundbeck & Co As H | Metodo para la preparacion de 5-cianoftalida |
| ES2195554T5 (es) | 1999-04-14 | 2010-02-02 | H. Lundbeck A/S | Metodo para la preparacion de 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 |
| ES2169709A1 (es) | 1999-10-25 | 2002-07-01 | Lundbeck & Co As H | Metodo para la preparacion de citalopram |
| AR026063A1 (es) | 1999-11-01 | 2002-12-26 | Lundbeck & Co As H | Metodo para la preparacion de 5-carboxiftalida. |
| AU778751B2 (en) | 1999-12-28 | 2004-12-16 | H. Lundbeck A/S | Method for the preparation of citalopram |
| ATE253568T1 (de) | 1999-12-30 | 2003-11-15 | Lundbeck & Co As H | Verfahren zur herstellung von citalopram |
| WO2001051477A1 (en) | 2000-01-14 | 2001-07-19 | H. Lundbeck A/S | Method for the preparation of 5-cyanophthalide |
| 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. |
| 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 |
| NL1017500C1 (nl) | 2000-03-13 | 2001-04-26 | Lundbeck & Co As H | Werkwijze voor de bereiding van Citalopram. |
| PL360110A1 (en) | 2000-03-13 | 2004-09-06 | H.Lundbeck A/S | Method for the preparation of citalopram |
| PL360107A1 (en) | 2000-03-14 | 2004-09-06 | H.Lundbeck A/S | Method for the preparation of citalopram |
| CZ20023406A3 (cs) * | 2000-03-16 | 2003-01-15 | H. Lundbeck A/S | Způsob výroby 5-kyano-1-(4-fluorfenyl)-1,3-dihydroisobenzofuranu |
| 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 |
| CA2360303C (en) | 2000-12-22 | 2003-08-12 | Marco Villa | Process for the preparation of pure citalopram |
| EP1181272B1 (en) | 2000-12-28 | 2002-08-28 | H. Lundbeck A/S | Process for the preparation of pure citalopram |
| CA2435925A1 (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 |
| FI20021421A0 (fi) * | 2002-07-30 | 2002-07-30 | Orion Corp Fermion | Valmistusmenetelmä |
| 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 |
| 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 |
| GB0601286D0 (en) * | 2006-01-23 | 2006-03-01 | Sandoz Ag | Asymmetric synthesis |
| US9339500B2 (en) * | 2008-03-04 | 2016-05-17 | Intra-Cellular Therapies, Inc. | Methods of treating vasomotor symptoms |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1143702A (da) | 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 |
| 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 |
| DK1015416T3 (da) | 1997-07-08 | 2001-11-05 | Lundbeck & Co As H | Fremgangsmåde til fremstilling af citalopram |
| UA62985C2 (en) * | 1997-11-10 | 2004-01-15 | Lunnbeck As H | A method for the preparation of citalopram |
| JP3813820B2 (ja) | 1997-11-11 | 2006-08-23 | 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 |
| EA002977B1 (ru) | 1998-10-20 | 2002-12-26 | Х.Лундбекк А/С | Способ получения циталопрама |
| PT1140886E (pt) | 1998-12-23 | 2003-08-29 | Lundbeck & Co As H | Metodo para a preparacao de 5- cianoftalida |
| AR022329A1 (es) | 1999-01-29 | 2002-09-04 | Lundbeck & Co As H | Metodo para la preparacion de 5-cianoftalida |
| ES2195554T5 (es) | 1999-04-14 | 2010-02-02 | H. Lundbeck A/S | Metodo para la preparacion de 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 |
| ES2169709A1 (es) | 1999-10-25 | 2002-07-01 | Lundbeck & Co As H | Metodo para la preparacion de 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 |
| JP4025501B2 (ja) | 2000-03-03 | 2007-12-19 | 株式会社ソニー・コンピュータエンタテインメント | 楽音発生装置 |
| CA2360303C (en) | 2000-12-22 | 2003-08-12 | Marco Villa | Process for the preparation of pure citalopram |
| EP1181272B1 (en) | 2000-12-28 | 2002-08-28 | H. Lundbeck A/S | Process for the preparation of pure citalopram |
-
1999
- 1999-10-25 ES ES200150056A patent/ES2169709A1/es active Pending
- 1999-10-25 AU AU63265/99A patent/AU742554B2/en not_active Ceased
- 1999-10-25 TR TR2001/01874T patent/TR200101874T1/xx unknown
- 1999-10-25 CH CH02004/01A patent/CH692298A5/de not_active IP Right Cessation
- 1999-10-25 EP EP99950511A patent/EP1228056B1/en not_active Expired - Lifetime
- 1999-10-25 SK SK924-2001A patent/SK287139B6/sk not_active IP Right Cessation
- 1999-10-25 WO PCT/DK1999/000581 patent/WO2000012044A2/en active Application Filing
- 1999-10-25 ES ES99950511T patent/ES2229774T3/es not_active Expired - Lifetime
- 1999-10-25 GB GB0115030A patent/GB2360281B/en not_active Revoked
- 1999-10-25 CH CH01179/01A patent/CH692421A5/de not_active IP Right Cessation
-
2001
- 2001-06-20 DK DK200100959A patent/DK200100959A/da not_active Application Discontinuation
- 2001-06-25 NO NO20013185A patent/NO325185B1/no not_active IP Right Cessation
- 2001-06-25 US US09/891,874 patent/US6407267B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20020035277A1 (en) | 2002-03-21 |
| SK287139B6 (sk) | 2010-01-07 |
| CH692298A5 (de) | 2002-04-30 |
| TR200101874T1 (tr) | 2002-02-21 |
| AU6326599A (en) | 2000-03-21 |
| NO325185B1 (no) | 2008-02-11 |
| ES2169709A1 (es) | 2002-07-01 |
| GB2360281A (en) | 2001-09-19 |
| CH692421A5 (de) | 2002-06-14 |
| GB2360281B (en) | 2002-01-16 |
| SK9242001A3 (en) | 2001-12-03 |
| GB0115030D0 (en) | 2001-08-08 |
| WO2000012044A3 (en) | 2000-08-03 |
| ES2229774T3 (es) | 2005-04-16 |
| NO20013185L (no) | 2001-08-24 |
| US6407267B1 (en) | 2002-06-18 |
| AU742554B2 (en) | 2002-01-03 |
| WO2000012044A2 (en) | 2000-03-09 |
| NO20013185D0 (no) | 2001-06-25 |
| EP1228056B1 (en) | 2004-09-22 |
| EP1228056A2 (en) | 2002-08-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AHS | Application shelved for other reasons than non-payment |