AR036212A1 - Proceso para la preparacion de citalopram y compuestos intermediarios usados en dicho proceso - Google Patents
Proceso para la preparacion de citalopram y compuestos intermediarios usados en dicho procesoInfo
- Publication number
- AR036212A1 AR036212A1 ARP020102955A ARP020102955A AR036212A1 AR 036212 A1 AR036212 A1 AR 036212A1 AR P020102955 A ARP020102955 A AR P020102955A AR P020102955 A ARP020102955 A AR P020102955A AR 036212 A1 AR036212 A1 AR 036212A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- citalopram
- group
- defined above
- oxime
- Prior art date
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
-
- 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
- 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)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Pain & Pain Management (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Proceso para la preparación de citalopram que comprende: (a) tratar una 5-formilftalida de fórmula (1) con una hidroxilamina de fórmula R-O-NH2 (2) donde R representa un átomo de hidrógeno o un sustituyente R'' inerte bajo las condiciones de una reacción Grignard; (b) hacer reaccionar la oxima obtenida de esa manera de fórmula (3) donde R tiene los valores definidos anteriormente; con un halogenuro de 4-fluorofenilmagnesio, directamente cuando R = R' o por sustitución de R por R' cuando R = H; (c) hacer reaccionar la cetona intermediaria de fórmula (4) donde R' tiene los valores definidos anteriormente y R'' representa MgHal donde Hal es halógeno, o hidrógeno, con un halogenuro de [3-(dimetilamino) propil] magnesio; (d) ciclizar el diol intermediario de fórmula (5) donde R' tiene los valores definidos anteriormente; (e) eliminar el grupo R' de la oxima sustituida de fórmula (6) donde R' se definió anteriormente; y (f) convertir el grupo oxiimino sustituido de la oxima de fórmula (7) en nitrilo, para dar citalopram o una de sus sales aceptables para uso farmacéutico; o (c') opcionalmente, si R' es trifenilmetilo o difenilmetilo, convertir directamente el grupo oxiimino sustituido de la oxima de fórmula (6) en nitrilo por tratamiento con un anhídrido mixto de formula H-CO-O-CO-R''' (8) donde R''' representa un grupo alquilo C1-6, un grupo aralquilo o un grupo arilo, para dar citalopram (A) o una sal farmacéuticamente aceptable del mismo. También se revelan los compuestos de fórmulas (3), (4), (5) y (6) y su uso como intermediarios en el proceso de síntesis de Citalopram que es un compuesto utilizado en la preparación de composiciones farmacéuticas indicadas para el tratamiento de la depresión.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01830517A EP1281707B1 (en) | 2001-08-02 | 2001-08-02 | Process for the preparation of 5-subtituted isobenzofurans |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR036212A1 true AR036212A1 (es) | 2004-08-18 |
Family
ID=8184643
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP020102955A AR036212A1 (es) | 2001-08-02 | 2002-08-02 | Proceso para la preparacion de citalopram y compuestos intermediarios usados en dicho proceso |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US7166729B2 (es) |
| EP (1) | EP1281707B1 (es) |
| JP (1) | JP2005501056A (es) |
| KR (1) | KR20040043176A (es) |
| CN (1) | CN1298713C (es) |
| AR (1) | AR036212A1 (es) |
| AT (1) | ATE286037T1 (es) |
| AU (1) | AU2002325385B2 (es) |
| BG (1) | BG108554A (es) |
| BR (1) | BR0211858A (es) |
| CA (1) | CA2456004A1 (es) |
| DE (1) | DE60108105T2 (es) |
| DK (1) | DK1281707T3 (es) |
| ES (1) | ES2234797T3 (es) |
| HK (1) | HK1070357A1 (es) |
| HU (1) | HUP0401166A3 (es) |
| MX (1) | MXPA04001030A (es) |
| PL (1) | PL368320A1 (es) |
| PT (1) | PT1281707E (es) |
| RO (1) | RO122147B1 (es) |
| TW (1) | TWI225055B (es) |
| WO (1) | WO2003011846A2 (es) |
| ZA (1) | ZA200400841B (es) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IS7239A (is) * | 2001-12-14 | 2004-04-29 | H. Lundbeck A/S | Aðferð til framleiðslu á essítalóprami |
| AU2003263155A1 (en) * | 2002-09-20 | 2004-04-08 | H. Lundbeck A/S | Method for manufacture of dihydroisobenzofuran derivatives |
| GB0601286D0 (en) | 2006-01-23 | 2006-03-01 | Sandoz Ag | Asymmetric synthesis |
| CA2932121A1 (en) | 2007-11-30 | 2009-06-11 | Newlink Genetics Corporation | Ido inhibitors |
| CN106632182A (zh) * | 2016-12-07 | 2017-05-10 | 万全万特制药（厦门）有限公司 | 草酸艾司西酞普兰脱甲基杂质的制备方法 |
| DE112019006382T8 (de) * | 2018-12-22 | 2021-12-09 | Malladi Drugs And Pharmaceuticals Ltd. | NEUES VERFAHREN ZUR HERSTELLUNG VONR-PHENYLACETYLCARBINOL UND β-AMINOALKOHOLEN |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| NZ501737A (en) * | 1997-07-08 | 2001-10-26 | H | Method for the preparation of citalopram using Grignard reagent 4-halogen-fluorophenyl and 3-halogen-N,N-dimethyl-propylamine |
| CZ296537B6 (cs) * | 1999-04-14 | 2006-04-12 | H. Lundbeck A/S | Zpusob výroby citalopramu a meziprodukty |
| ITMI991486A1 (it) * | 1999-07-06 | 2001-01-06 | Vis Farmaceutici S P A | Processo per la sintesi di citalopram |
| IES20010143A2 (en) * | 2000-02-24 | 2001-07-25 | 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. |
-
2001
- 2001-08-02 DE DE60108105T patent/DE60108105T2/de not_active Expired - Fee Related
- 2001-08-02 DK DK01830517T patent/DK1281707T3/da active
- 2001-08-02 EP EP01830517A patent/EP1281707B1/en not_active Expired - Lifetime
- 2001-08-02 ES ES01830517T patent/ES2234797T3/es not_active Expired - Lifetime
- 2001-08-02 AT AT01830517T patent/ATE286037T1/de not_active IP Right Cessation
- 2001-08-02 PT PT01830517T patent/PT1281707E/pt unknown
-
2002
- 2002-07-29 RO ROA200400084A patent/RO122147B1/ro unknown
- 2002-07-29 KR KR10-2004-7001616A patent/KR20040043176A/ko not_active Application Discontinuation
- 2002-07-29 AU AU2002325385A patent/AU2002325385B2/en not_active Ceased
- 2002-07-29 BR BR0211858-0A patent/BR0211858A/pt not_active IP Right Cessation
- 2002-07-29 CA CA002456004A patent/CA2456004A1/en not_active Abandoned
- 2002-07-29 CN CNB028183231A patent/CN1298713C/zh not_active Expired - Fee Related
- 2002-07-29 MX MXPA04001030A patent/MXPA04001030A/es active IP Right Grant
- 2002-07-29 HU HU0401166A patent/HUP0401166A3/hu unknown
- 2002-07-29 JP JP2003517038A patent/JP2005501056A/ja active Pending
- 2002-07-29 PL PL02368320A patent/PL368320A1/xx not_active Application Discontinuation
- 2002-07-29 WO PCT/EP2002/008550 patent/WO2003011846A2/en active Application Filing
- 2002-07-31 TW TW091117176A patent/TWI225055B/zh active
- 2002-08-02 AR ARP020102955A patent/AR036212A1/es unknown
-
2004
- 2004-01-30 BG BG108554A patent/BG108554A/bg unknown
- 2004-01-31 US US10/776,625 patent/US7166729B2/en not_active Expired - Fee Related
- 2004-02-02 ZA ZA200400841A patent/ZA200400841B/en unknown
-
2005
- 2005-04-08 HK HK05102982A patent/HK1070357A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU2002325385B8 (en) | 2003-02-17 |
| PT1281707E (pt) | 2005-04-29 |
| HK1070357A1 (en) | 2005-06-17 |
| KR20040043176A (ko) | 2004-05-22 |
| EP1281707B1 (en) | 2004-12-29 |
| ES2234797T3 (es) | 2005-07-01 |
| US20040230065A1 (en) | 2004-11-18 |
| DE60108105T2 (de) | 2005-12-08 |
| TWI225055B (en) | 2004-12-11 |
| PL368320A1 (en) | 2005-03-21 |
| WO2003011846A3 (en) | 2003-11-27 |
| AU2002325385B2 (en) | 2007-07-05 |
| DE60108105D1 (de) | 2005-02-03 |
| BG108554A (bg) | 2005-03-31 |
| WO2003011846B1 (en) | 2003-12-24 |
| US7166729B2 (en) | 2007-01-23 |
| BR0211858A (pt) | 2004-09-21 |
| CA2456004A1 (en) | 2003-02-13 |
| DK1281707T3 (da) | 2005-05-02 |
| ATE286037T1 (de) | 2005-01-15 |
| WO2003011846A2 (en) | 2003-02-13 |
| MXPA04001030A (es) | 2004-12-03 |
| EP1281707A1 (en) | 2003-02-05 |
| CN1298713C (zh) | 2007-02-07 |
| ZA200400841B (en) | 2005-02-02 |
| CN1555370A (zh) | 2004-12-15 |
| JP2005501056A (ja) | 2005-01-13 |
| HUP0401166A2 (hu) | 2004-09-28 |
| RO122147B1 (ro) | 2009-01-30 |
| HUP0401166A3 (en) | 2007-05-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FB | Suspension of granting procedure |