PE20050065A1 - A PROCESS FOR THE PREPARATION OF CITALOPRAM RACEMIC DIOL OR CITALOPRAM S O R DIOLES - Google Patents
A PROCESS FOR THE PREPARATION OF CITALOPRAM RACEMIC DIOL OR CITALOPRAM S O R DIOLESInfo
- Publication number
- PE20050065A1 PE20050065A1 PE2004000033A PE2004000033A PE20050065A1 PE 20050065 A1 PE20050065 A1 PE 20050065A1 PE 2004000033 A PE2004000033 A PE 2004000033A PE 2004000033 A PE2004000033 A PE 2004000033A PE 20050065 A1 PE20050065 A1 PE 20050065A1
- Authority
- PE
- Peru
- Prior art keywords
- diol
- citalopram
- racemic
- preparation
- base
- Prior art date
Links
- 150000002009 diols Chemical class 0.000 title abstract 11
- 229960001653 citalopram Drugs 0.000 title abstract 10
- 238000000034 method Methods 0.000 title abstract 5
- 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 abstract 3
- 238000002360 preparation method Methods 0.000 title abstract 3
- 150000003839 salts Chemical class 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 abstract 2
- 239000012458 free base Substances 0.000 abstract 2
- 238000002955 isolation Methods 0.000 abstract 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical compound C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000002244 precipitate Substances 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/32—Separation; Purification; Stabilisation; Use of additives
- C07C253/34—Separation; Purification
-
- 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
- A61K31/275—Nitriles; Isonitriles
- A61K31/277—Nitriles; Isonitriles having a ring, e.g. verapamil
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
SE REFIERE A UN PROCESO PARA LA PREPARACION DE UNA BASE LIBRE DIOL RACEMICA DEL CITALOPRAM (CON DENOMINACION QUIMICA: 4-[4-(DIMETILAMINO)-1-(4'-FLUORFENIL)-1-HIDROXIBUTIL]-3-(HIDROXIMETIL)-BENZONITRILO) Y/O SAL DE ADICION DE ACIDO Y/O BASE LIBRE DIOL R O S Y/O SAL DE ADICION DE ACIDO, QUE COMPRENDE LA SEPARACION DE UNA MEZCLA INICIAL NO RACEMICA DEL DIOL R Y S-CITALOPRAM CON MAS DE 50% DE UNO DE LOS ENANTIOMEROS EN UNA FRACCION QUE ES ENRIQUECIDAS CON EL DIOL DEL S O R-CITALOPRAM Y UNA FRACCION QUE COMPRENDE DIOL DE RS-CITALOPRAM, EN DONDE LA RELACION DE DIOL R:DIOL S ES IGUAL 1:1 O MAS CERCANA A 1:1 QUE EN LA MEZCLA INICIAL DE DIOL R Y S. EL METODO SE CARACTERIZA EN QUE i) EL DIOL DE RS-CITALOPRAM ESTA PRECIPITADO DE UNA SOLUCION DE LA MEZCLA INICIAL NO-RACEMICA, O EL DIOL DE R O S-CITALOPRAM SE DISUELVE EN UN SOLVENTE DE LA MEZCLA INICIAL NO RACEMICA, SALIENDO DE UN RESIDUO DEL DIOL DE RS-CITALOPRAM Y EN QUE ii) EL RESIDUO /PRECIPITADO SE SEPARA DE LA FASE DE SOLUCION FINAL; SEGUIDA POR PASOS OPCIONALES DE LA REPETICION, DE LA RECRISTALIZACION, DE LA PURIFICACION, AISLAMIENTO, DEL AISLAMIENTO Y DE LA CONVERSION ENTRE LA BASE Y LAS SALES LIBRES. TAMBIEN SE REFIERE CON UN PROCESO PARA LA PREPARACION DE RS-, S-, O R- CITALOPRAM (TODO COMO BASE Y/O SAL LIBRES DE LA ADICION DE ACIDO) ABARCANDO EL METODO DESCRITO Y SEGUIDO POR EL ENCIERRO DEL ANILLOIT REFERS TO A PROCESS FOR THE PREPARATION OF A RACEMIC DIOL FREE BASE OF CITALOPRAM (WITH CHEMICAL NAME: 4- [4- (DIMETHYLAMINE) -1- (4'-FLUORPHENIL) -1-HYDROXIBUTYL] -3- (HYDROXIMETHYL) - BENZONITRILE) AND / OR ACID ADDITION SALT AND / OR DIOL ROSY FREE BASE / OR ACID ADDITION SALT, WHICH INCLUDES THE SEPARATION OF AN INITIAL NON-RACEMIC MIXTURE OF DIOL RY S-CITALOPRAM WITH MORE THAN 50% OF ONE OF THE ENANTIOMERS IN A FRACTION THAT IS ENRICHED WITH THE DIOL OF SO R-CITALOPRAM AND A FRACTION THAT INCLUDES DIOL OF RS-CITALOPRAM, WHERE THE RATIO OF DIOL R: DIOL S IS EQUAL 1: 1 OR CLOSER TO 1: 1 THAN IN THE INITIAL MIX OF DIOL RY S. THE METHOD IS CHARACTERIZED IN THAT i) THE DIOL OF RS-CITALOPRAM IS PRECIPITATED FROM A SOLUTION OF THE INITIAL NON-RACEMIC MIXTURE, OR THE DIOL OF RO S-CITALOPRAM IS DISSOLVES IN A SOLVENT OF THE INITIAL MIXTURE NOT RACEMIC, COMING OUT OF A RESIDUE OF RS-CITALOPRAM DIOL AND IN WHICH ii) THE RESIDUE / PRECIPITATE IS SEPARATED FROM THE FINAL SOLUTION PHASE; FOLLOWED BY OPTIONAL STEPS OF REPETITION, RECRYSTALIZATION, PURIFICATION, ISOLATION, ISOLATION AND CONVERSION BETWEEN BASE AND FREE SALTS. IT ALSO REFERS TO A PROCESS FOR THE PREPARATION OF RS-, S-, OR R- CITALOPRAM (ALL AS BASE AND / OR SALT FREE FROM THE ADDITION OF ACID) INCLUDING THE METHOD DESCRIBED AND FOLLOWED BY THE ENCLOSURE OF THE RING
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200202004 | 2002-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE20050065A1 true PE20050065A1 (en) | 2005-02-18 |
Family
ID=35423357
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2004000033A PE20050065A1 (en) | 2002-12-23 | 2004-01-05 | A PROCESS FOR THE PREPARATION OF CITALOPRAM RACEMIC DIOL OR CITALOPRAM S O R DIOLES |
Country Status (17)
| Country | Link |
|---|---|
| KR (1) | KR101076640B1 (en) |
| CN (1) | CN100334071C (en) |
| AR (1) | AR042655A1 (en) |
| BR (1) | BR0317629A (en) |
| DK (1) | DK1581483T3 (en) |
| EA (1) | EA009061B1 (en) |
| ES (1) | ES2385975T3 (en) |
| ME (1) | MEP5708A (en) |
| MY (1) | MY142404A (en) |
| PE (1) | PE20050065A1 (en) |
| PT (1) | PT1581483E (en) |
| RS (1) | RS52152B (en) |
| SI (1) | SI1581483T1 (en) |
| TW (1) | TWI331605B (en) |
| UA (1) | UA84859C2 (en) |
| UY (1) | UY28146A1 (en) |
| ZA (1) | ZA200504715B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA95199U (en) | 2014-07-09 | 2014-12-10 | PRECISION DISPOSER WITH ACCURATE DOSAGE FOR Bulk Products | |
| CN110590602B (en) * | 2019-09-25 | 2022-04-05 | 浙江海森药业股份有限公司 | Resolution refining method of racemic citalopram diol |
| CN114763329A (en) * | 2021-01-14 | 2022-07-19 | 浙江华海药业股份有限公司 | Method for purifying citalopram key intermediate |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8814057D0 (en) * | 1988-06-14 | 1988-07-20 | Lundbeck & Co As H | New enantiomers & their isolation |
| AR034612A1 (en) * | 2001-06-25 | 2004-03-03 | Lundbeck & Co As H | PROCESS FOR THE PREPARATION OF RACEMIC CITALOPRAM AND / OR OF THE S- OR R-CITALOPRAM THROUGH THE SEPARATION OF A MIXING OF R- AND S-CITALOPRAM |
-
2003
- 2003-12-18 KR KR1020057011898A patent/KR101076640B1/en not_active Expired - Fee Related
- 2003-12-18 RS YU20050488A patent/RS52152B/en unknown
- 2003-12-18 BR BR0317629-0A patent/BR0317629A/en not_active Application Discontinuation
- 2003-12-18 DK DK03767476.9T patent/DK1581483T3/en active
- 2003-12-18 PT PT03767476T patent/PT1581483E/en unknown
- 2003-12-18 CN CNB200380107283XA patent/CN100334071C/en not_active Expired - Lifetime
- 2003-12-18 ES ES03767476T patent/ES2385975T3/en not_active Expired - Lifetime
- 2003-12-18 SI SI200332174T patent/SI1581483T1/en unknown
- 2003-12-18 EA EA200501042A patent/EA009061B1/en not_active IP Right Cessation
- 2003-12-18 UA UAA200506921A patent/UA84859C2/en unknown
- 2003-12-18 ME MEP-57/08A patent/MEP5708A/en unknown
- 2003-12-18 TW TW092135925A patent/TWI331605B/en not_active IP Right Cessation
- 2003-12-22 UY UY28146A patent/UY28146A1/en not_active Application Discontinuation
- 2003-12-22 AR ARP030104781A patent/AR042655A1/en unknown
- 2003-12-22 MY MYPI20034948A patent/MY142404A/en unknown
-
2004
- 2004-01-05 PE PE2004000033A patent/PE20050065A1/en not_active Application Discontinuation
-
2005
- 2005-06-09 ZA ZA200504715A patent/ZA200504715B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RS20050488A (en) | 2007-06-04 |
| CN100334071C (en) | 2007-08-29 |
| KR101076640B1 (en) | 2011-10-27 |
| ZA200504715B (en) | 2006-08-30 |
| EA009061B1 (en) | 2007-10-26 |
| CN1729164A (en) | 2006-02-01 |
| DK1581483T3 (en) | 2012-07-23 |
| SI1581483T1 (en) | 2012-09-28 |
| AR042655A1 (en) | 2005-06-29 |
| RS52152B (en) | 2012-08-31 |
| BR0317629A (en) | 2005-11-29 |
| UA84859C2 (en) | 2008-12-10 |
| PT1581483E (en) | 2012-07-24 |
| KR20050093801A (en) | 2005-09-23 |
| TWI331605B (en) | 2010-10-11 |
| UY28146A1 (en) | 2004-07-30 |
| ES2385975T3 (en) | 2012-08-06 |
| EA200501042A1 (en) | 2005-12-29 |
| ME00034B (en) | 2010-02-10 |
| TW200512202A (en) | 2005-04-01 |
| MEP5708A (en) | 2010-02-10 |
| MY142404A (en) | 2010-11-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant, registration | ||
| FD | Application declared void or lapsed |