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
- 229960001653 citalopram Drugs 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 4
- 150000001875 compounds Chemical class 0.000 title abstract 3
- 238000002360 preparation method Methods 0.000 title abstract 3
- WSEQXVZVJXJVFP-UHFFFAOYSA-N 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile Chemical class O1CC2=CC(C#N)=CC=C2C1(CCCN(C)C)C1=CC=C(F)C=C1 WSEQXVZVJXJVFP-UHFFFAOYSA-N 0.000 title 1
- 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 4
- 150000002923 oximes Chemical class 0.000 abstract 4
- -1 4-fluorophenylmagnesium halide Chemical class 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 150000002825 nitriles Chemical class 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- DBSGLQIKLWDTTD-UHFFFAOYSA-N 1-oxo-3h-2-benzofuran-5-carbaldehyde Chemical compound O=CC1=CC=C2C(=O)OCC2=C1 DBSGLQIKLWDTTD-UHFFFAOYSA-N 0.000 abstract 1
- VLQBZZYXIIHJIP-UHFFFAOYSA-N CN(C)CCC[Mg] Chemical compound CN(C)CCC[Mg] VLQBZZYXIIHJIP-UHFFFAOYSA-N 0.000 abstract 1
- 238000003747 Grignard reaction Methods 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 150000002009 diols Chemical class 0.000 abstract 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 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
-
- 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 (22)
| 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) |
| 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 |
| WO2004026855A1 (en) * | 2002-09-20 | 2004-04-01 | H. Lundbeck A/S | Method for manufacture of dihydroisobenzofuran derivatives |
| GB0601286D0 (en) * | 2006-01-23 | 2006-03-01 | Sandoz Ag | Asymmetric synthesis |
| CN101932325B (zh) | 2007-11-30 | 2014-05-28 | 新联基因公司 | Ido抑制剂 |
| 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 |
| CN113784945A (zh) * | 2018-12-22 | 2021-12-10 | 马拉迪制药有限公司 | 制备R-苯基乙酰基甲醇和β-氨基醇的新方法 |
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 |
| TR200000066T2 (tr) * | 1997-07-08 | 2000-11-21 | H. Lundbeck A/S | Sitalopram hazırlanması için yöntem. |
| NZ514671A (en) * | 1999-04-14 | 2003-10-31 | H | Method for the preparation of citalopram |
| 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 PT PT01830517T patent/PT1281707E/pt unknown
- 2001-08-02 ES ES01830517T patent/ES2234797T3/es not_active Expired - Lifetime
- 2001-08-02 DK DK01830517T patent/DK1281707T3/da active
- 2001-08-02 DE DE60108105T patent/DE60108105T2/de not_active Expired - Fee Related
- 2001-08-02 AT AT01830517T patent/ATE286037T1/de not_active IP Right Cessation
- 2001-08-02 EP EP01830517A patent/EP1281707B1/en not_active Expired - Lifetime
-
2002
- 2002-07-29 AU AU2002325385A patent/AU2002325385B2/en not_active Ceased
- 2002-07-29 PL PL02368320A patent/PL368320A1/xx not_active Application Discontinuation
- 2002-07-29 CN CNB028183231A patent/CN1298713C/zh not_active Expired - Fee Related
- 2002-07-29 KR KR10-2004-7001616A patent/KR20040043176A/ko not_active Ceased
- 2002-07-29 MX MXPA04001030A patent/MXPA04001030A/es active IP Right Grant
- 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 WO PCT/EP2002/008550 patent/WO2003011846A2/en not_active Ceased
- 2002-07-29 RO ROA200400084A patent/RO122147B1/ro unknown
- 2002-07-29 HU HU0401166A patent/HUP0401166A3/hu unknown
- 2002-07-29 JP JP2003517038A patent/JP2005501056A/ja active Pending
- 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
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003011846B1 (en) | 2003-12-24 |
| HK1070357A1 (zh) | 2005-06-17 |
| US7166729B2 (en) | 2007-01-23 |
| BG108554A (bg) | 2005-03-31 |
| HUP0401166A2 (hu) | 2004-09-28 |
| WO2003011846A2 (en) | 2003-02-13 |
| AU2002325385B8 (en) | 2003-02-17 |
| CN1298713C (zh) | 2007-02-07 |
| DE60108105T2 (de) | 2005-12-08 |
| CA2456004A1 (en) | 2003-02-13 |
| DK1281707T3 (da) | 2005-05-02 |
| EP1281707A1 (en) | 2003-02-05 |
| BR0211858A (pt) | 2004-09-21 |
| TWI225055B (en) | 2004-12-11 |
| MXPA04001030A (es) | 2004-12-03 |
| EP1281707B1 (en) | 2004-12-29 |
| US20040230065A1 (en) | 2004-11-18 |
| JP2005501056A (ja) | 2005-01-13 |
| PT1281707E (pt) | 2005-04-29 |
| PL368320A1 (en) | 2005-03-21 |
| ATE286037T1 (de) | 2005-01-15 |
| KR20040043176A (ko) | 2004-05-22 |
| DE60108105D1 (de) | 2005-02-03 |
| ES2234797T3 (es) | 2005-07-01 |
| AU2002325385B2 (en) | 2007-07-05 |
| CN1555370A (zh) | 2004-12-15 |
| HUP0401166A3 (en) | 2007-05-29 |
| ZA200400841B (en) | 2005-02-02 |
| WO2003011846A3 (en) | 2003-11-27 |
| RO122147B1 (ro) | 2009-01-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FB | Suspension of granting procedure |