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
Links
- 229960001653 citalopram Drugs 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- WSEQXVZVJXJVFP-UHFFFAOYSA-N 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile Chemical compound O1CC2=CC(C#N)=CC=C2C1(CCCN(C)C)C1=CC=C(F)C=C1 WSEQXVZVJXJVFP-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 4
- WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 abstract 2
- 239000007818 Grignard reagent Substances 0.000 abstract 2
- 150000004795 grignard reagents Chemical class 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/38—Compounds 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic 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
- C07C235/84—Carboxylic 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic 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
- C07C237/30—Carboxylic 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
-
- 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
- C07D307/88—Benzo [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)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (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.
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) | DE1015416T1 (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)
| 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 |
| CA2291134C (en) | 1998-10-20 | 2006-05-23 | H. Lundbeck A/S | Method for the preparation of citalopram |
| 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 |
| AU759716B2 (en) * | 1999-04-14 | 2003-04-17 | H. Lundbeck A/S | 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 |
| 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 |
| 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. |
| TR200401456T1 (tr) * | 1999-10-25 | 2005-04-21 | H. Lundbeck A/S | Sitalopram hazırlanması için yöntem. |
| 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 |
| BR9917604A (pt) | 1999-12-30 | 2002-12-31 | Lundbeck & Co As H | Método para preparação de citalopram |
| HUP0300343A2 (hu) | 2000-01-14 | 2003-06-28 | H. Lundbeck A/S | Eljárás 5-cianoftalid előállítására |
| 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. |
| IES20010157A2 (en) | 2000-03-03 | 2002-03-06 | 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 |
| NL1017500C1 (nl) | 2000-03-13 | 2001-04-26 | Lundbeck & Co As H | Werkwijze voor de bereiding van Citalopram. |
| CN1427835A (zh) * | 2000-03-13 | 2003-07-02 | H·隆德贝克有限公司 | 5－取代的1－(4－氟苯基)－1,3－二氢异苯并呋喃的分步烷基化 |
| PL360110A1 (en) | 2000-03-13 | 2004-09-06 | H.Lundbeck A/S | Method for the preparation of citalopram |
| TR200202155T2 (tr) | 2000-03-14 | 2002-12-23 | H. Lundbeck A/S | Sitalopramin preparasyon metodu |
| 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 |
| CA2354877C (en) * | 2000-08-18 | 2006-05-02 | H. Lundbeck A/S | 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. |
| NL1017525C1 (nl) * | 2000-12-22 | 2001-04-26 | Lundbeck & Co As H | Werkwijze voor de bereiding van zuiver Citalopram |
| ATE222899T1 (de) * | 2000-12-28 | 2002-09-15 | Lundbeck & Co As H | Verfahren zur herstellung von reinem 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 | |
| BR0206164A (pt) | 2001-07-31 | 2003-10-28 | Lundbeck & Co As H | Partìculas cristalinas de oxalato de escitalopram, método para a produção de partìculas cristalinas de oxalato de escitalopram, e, forma de dosagem unitária sólida |
| DE60108105T2 (de) * | 2001-08-02 | 2005-12-08 | Infosint Sa | Verfahren zur Herstellung von 5-substituierten Isobenzofuranen |
| 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 |
| 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 |
| 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. |
| US7687645B2 (en) | 2003-03-21 | 2010-03-30 | H. Lundbeck A/S | Intermediates for the preparation of citalopram and escitalopram |
| 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 |
| ES2240931T3 (es) * | 2003-10-28 | 2005-10-16 | Adorkem Technology Spa | Procedimiento para la preparacion de citalopram. |
| US7790935B2 (en) | 2004-08-23 | 2010-09-07 | Sun Pharma Global Fze | Process for preparation of citalopram and enantiomers |
| TWI358407B (en) | 2005-06-22 | 2012-02-21 | Lundbeck & Co As H | Crystalline base of escitalopram and orodispersibl |
| US7834201B2 (en) | 2005-06-22 | 2010-11-16 | H. Lundbeck A/S | Crystalline base of escitalopram and orodispersible tablets comprising escitalopram base |
| US9339500B2 (en) * | 2008-03-04 | 2016-05-17 | Intra-Cellular Therapies, Inc. | Methods of treating vasomotor symptoms |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1143702A (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 |
-
1998
- 1998-03-03 WO PCT/DK1998/000081 patent/WO1998019513A2/en not_active Ceased
- 1998-03-03 KR KR1020007000063A patent/KR100357975B1/ko not_active Expired - Fee Related
- 1998-03-03 DE DE1015416T patent/DE1015416T1/de active Pending
- 1998-03-03 SK SK3-2000A patent/SK283309B6/sk not_active IP Right Cessation
- 1998-03-03 CZ CZ200062A patent/CZ291440B6/cs not_active IP Right Cessation
- 1998-03-03 AU AU66098/98A patent/AU737610B2/en not_active Ceased
- 1998-03-03 IL IL13351198A patent/IL133511A/en not_active IP Right Cessation
- 1998-03-03 CA CA002291067A patent/CA2291067C/en not_active Expired - Fee Related
- 1998-03-03 CN CNB2003101164072A patent/CN1206207C/zh not_active Expired - Fee Related
- 1998-03-03 NZ NZ501737A patent/NZ501737A/en unknown
- 1998-03-03 JP JP52097198A patent/JP3526581B2/ja not_active Expired - Fee Related
- 1998-03-03 HU HU0003177A patent/HU228744B1/hu not_active IP Right Cessation
- 1998-03-03 AT AT98905125T patent/ATE205824T1/de active
- 1998-03-03 ES ES98905125T patent/ES2148120T3/es not_active Expired - Lifetime
- 1998-03-03 EP EP98905125A patent/EP1015416B1/en not_active Expired - Lifetime
- 1998-03-03 DK DK98905125T patent/DK1015416T3/da active
- 1998-03-03 PT PT98905125T patent/PT1015416E/pt unknown
- 1998-03-03 TR TR2000/00066T patent/TR200000066T2/xx unknown
- 1998-03-03 EA EA200000102A patent/EA001728B1/ru not_active IP Right Cessation
- 1998-03-03 DE DE69801764T patent/DE69801764T2/de not_active Expired - Lifetime
-
1999
- 1999-12-14 IS IS5300A patent/IS2023B/is unknown
-
2000
- 2000-01-03 NO NO20000008A patent/NO322146B1/no not_active IP Right Cessation
- 2000-01-07 US US09/479,832 patent/US6229026B1/en not_active Expired - Lifetime
- 2000-01-31 BG BG104116A patent/BG64823B1/bg unknown
-
2002
- 2002-11-27 IL IL153125A patent/IL153125A/en not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG2A | Definitive protection |
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