HUP0300212A2 - Eljárás citalopram előállítására - Google Patents
Eljárás citalopram előállításáraInfo
- Publication number
- HUP0300212A2 HUP0300212A2 HU0300212A HUP0300212A HUP0300212A2 HU P0300212 A2 HUP0300212 A2 HU P0300212A2 HU 0300212 A HU0300212 A HU 0300212A HU P0300212 A HUP0300212 A HU P0300212A HU P0300212 A2 HUP0300212 A2 HU P0300212A2
- Authority
- HU
- Hungary
- Prior art keywords
- group
- formula
- alkyl
- compound
- citalopram
- Prior art date
Links
- 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 title abstract 3
- 229960001653 citalopram Drugs 0.000 title abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 2
- 125000006239 protecting group Chemical group 0.000 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 abstract 1
- 101100439663 Arabidopsis thaliana CHR7 gene Proteins 0.000 abstract 1
- 125000003158 alcohol group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 230000001430 anti-depressive effect Effects 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 229940005513 antidepressants Drugs 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 abstract 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 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
- A61P25/24—Antidepressants
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Neurology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Steroid Compounds (AREA)
Abstract
A találmány tárgya eljárás a jól ismert antidepresszáns hatásúcitalopram, azaz 1-[3-(dimetilamino)propil]-1-(4-fluorfenil)-1,3-dihidro-5-izobenzofuránkarbonitril előállítására. A találmányértelmében úgy járnak el, hogy az (I) képletű vegyületet valamely (II)általános képletű vegyülettel - a képletben X jelentése alkalmaskilépőcsoport, továbbá R jelentése -CH2-O-Pg, -CH2-NPg1Pg2, -CH2-NMePg1, -CO-N(CH3)2, -CH(OR1)(OR2), -C(OR4)(OR5)(OR6), -COOR3, -CH2-CO-NH2, -CH=CHR7 vagy -CO-NHR8 általános képletű csoport, melycsoportokban Pg jelentése az alkoholcsoport vonatkozásábanvédőcsoport, Pg1 és Pg2 jelentése az aminocsoport vonatkozásábanvédőcsoport, R1 és R2 egymástól függetlenül alkil-, alkenil-, alkinil-vagy adott esetben alkilcsoporttal szubsztituált aril- vagyaralkilcsoportokat jelentenek vagy R1 és R2 együtt 2-4 szénatomottartalmazó láncot képeznek, R3, R4, R5, R6 és R7 egymástól függetlenülalkil-, alkenil-, alkinil- vagy adott esetben alkilcsoporttal adottesetben szubsztituált aril- vagy aralkilcsoportot jelent és R8jelentése hidrogénatom vagy metilcsoport - reagáltatnak, majd egy ígykapott (III) általános képletű vegyület - a képletben R jelentése akorábban megadott - R csoportját dimetilaminometilcsoporttá alakítják,végül a citalopramot szabad bázisként vagy gyógyászatilag elfogadhatósóként elkülönítik. Ó
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200000296 | 2000-02-24 | ||
| DKPA200000401 | 2000-03-13 | ||
| PCT/DK2001/000123 WO2001043525A2 (en) | 2000-02-24 | 2001-02-22 | Method for the preparation of citalopram |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HUP0300212A2 true HUP0300212A2 (hu) | 2003-06-28 |
Family
ID=26068779
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0300212A HUP0300212A2 (hu) | 2000-02-24 | 2001-02-22 | Eljárás citalopram előállítására |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US6420574B2 (hu) |
| EP (1) | EP1259501A2 (hu) |
| JP (1) | JP2003523955A (hu) |
| KR (1) | KR20020081355A (hu) |
| CN (1) | CN1608057A (hu) |
| AR (1) | AR029658A1 (hu) |
| AU (1) | AU2001235358A1 (hu) |
| BE (1) | BE1011177A6 (hu) |
| BG (1) | BG107061A (hu) |
| BR (1) | BR0108937A (hu) |
| CA (1) | CA2401236A1 (hu) |
| EA (1) | EA005315B1 (hu) |
| FR (1) | FR2805812A1 (hu) |
| GR (1) | GR1004073B (hu) |
| HR (1) | HRP20020660A2 (hu) |
| HU (1) | HUP0300212A2 (hu) |
| IE (1) | IES20010163A2 (hu) |
| IL (1) | IL151059A0 (hu) |
| IS (1) | IS6487A (hu) |
| IT (1) | ITMI20010386A1 (hu) |
| MX (1) | MXPA02008228A (hu) |
| NL (1) | NL1017415C1 (hu) |
| NO (1) | NO20023928D0 (hu) |
| PL (1) | PL363119A1 (hu) |
| SK (1) | SK13672002A3 (hu) |
| WO (1) | WO2001043525A2 (hu) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR022329A1 (es) | 1999-01-29 | 2002-09-04 | Lundbeck & Co As H | Metodo para la preparacion de 5-cianoftalida |
| CN1142926C (zh) * | 1999-04-14 | 2004-03-24 | H·隆德贝克有限公司 | 制备西酞普兰的方法 |
| ITMI991581A1 (it) * | 1999-06-25 | 2001-01-15 | Lundbeck & Co As H | Metodo per la preparazione di citalopram |
| PT1298124E (pt) | 1999-10-25 | 2007-05-31 | Lundbeck & Co As H | Método para a preparação 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 |
| AR026063A1 (es) | 1999-11-01 | 2002-12-26 | Lundbeck & Co As H | Metodo para la preparacion de 5-carboxiftalida. |
| PT1246812E (pt) | 1999-12-28 | 2004-08-31 | Lundbeck & Co As H | Metodo para a preparacao de citalopram |
| EP1246813B1 (en) | 1999-12-30 | 2003-11-05 | H. Lundbeck A/S | Method for the preparation of citalopram |
| ATE252570T1 (de) * | 2000-01-14 | 2003-11-15 | Lundbeck & Co As H | Verfahren zur herstellung von 5-cyanophthalid |
| US6433196B1 (en) * | 2000-02-17 | 2002-08-13 | Sumika Fine Chemicals Co., Ltd. | Production method of citalopram, intermediate therefor and production method of the intermediate |
| NL1017417C1 (nl) * | 2000-03-03 | 2001-03-16 | Lundbeck & Co As H | Werkwijze voor de bereiding van Citalopram. |
| NZ521201A (en) | 2000-03-13 | 2004-02-27 | H | Method for the preparation of citalopram |
| IES20010206A2 (en) | 2000-03-13 | 2002-03-06 | Lundbeck & Co As H | Method for the preparation of citalopram |
| EP1265881A1 (en) * | 2000-03-13 | 2002-12-18 | H. Lundbeck A/S | Stepwise alkylation of 5-substituted 1-(4-fluorophenyl)-1,3-dihydroisobenzofurans |
| IL151488A0 (en) | 2000-03-14 | 2003-04-10 | Lundbeck & Co As H | Method for the preparation of citalopram |
| EA200200982A1 (ru) * | 2000-03-16 | 2003-02-27 | Х.Лундбекк А/С | Способ получения 5-циано-1-(4-фторфенил)-1,3-дигидроизобензофуранов |
| 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 |
| IL144816A (en) | 2000-08-18 | 2005-09-25 | 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 |
| AR034759A1 (es) * | 2001-07-13 | 2004-03-17 | Lundbeck & Co As H | Metodo para la preparacion de escitalopram |
| KR20050043776A (ko) * | 2001-11-08 | 2005-05-11 | 세프라코 아이엔시. | 거울상 이성질체로 농축된, 시탈로프람의 데스메틸 및디데스메틸 대사물을 이용한 우울증 및 다른 중추신경계질환 치료방법 |
| PE20040991A1 (es) | 2002-08-12 | 2004-12-27 | Lundbeck & Co As H | Separacion de intermediarios para la preparacion de escitalopram |
| TR200504022T1 (tr) * | 2003-03-24 | 2006-08-21 | Hetero Drugs Limited | (S)-sitalopram oksalatın yeni sıvı kristal formları. |
| WO2005047274A1 (en) * | 2003-11-12 | 2005-05-26 | Dr. Reddy's Laboratories, Inc. | Preparation of escitalopram |
| 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 |
| CA2685424A1 (en) * | 2007-05-18 | 2008-11-27 | Cipla Limited | Process for the preparation of escitalopram via desmethylcitalopram, optical resolution and methylation of the s-isomer |
| WO2009111031A2 (en) * | 2008-03-04 | 2009-09-11 | Intra-Cellular Therapies, Inc. | Methods of treating vasomotor symptoms |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1143702A (hu) | 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 |
| US5296007A (en) | 1986-11-17 | 1994-03-22 | Ensci Inc. | Process for removing sulfur from coal |
| GB8814057D0 (en) | 1988-06-14 | 1988-07-20 | Lundbeck & Co As H | New enantiomers & their isolation |
| 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 |
| DE1015416T1 (de) | 1997-07-08 | 2000-10-05 | Lundbeck A S Kobenhavn Valby H | Verfahren zur herstellung von 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 |
| WO2000023431A1 (en) | 1998-10-20 | 2000-04-27 | H. Lundbeck A/S | Method for the preparation of citalopram |
| EA003057B1 (ru) | 1998-12-23 | 2002-12-26 | Х.Лундбекк А/С | Способ получения 5-цианофталида |
| AR022329A1 (es) | 1999-01-29 | 2002-09-04 | Lundbeck & Co As H | Metodo para la preparacion de 5-cianoftalida |
| CN1142926C (zh) | 1999-04-14 | 2004-03-24 | H·隆德贝克有限公司 | 制备西酞普兰的方法 |
| 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 |
| EP1228056B1 (en) | 1999-10-25 | 2004-09-22 | H. Lundbeck A/S | Method for the preparation of 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 |
-
2001
- 2001-02-21 NL NL1017415A patent/NL1017415C1/nl not_active IP Right Cessation
- 2001-02-21 FR FR0102339A patent/FR2805812A1/fr active Pending
- 2001-02-22 SK SK1367-2002A patent/SK13672002A3/sk not_active Application Discontinuation
- 2001-02-22 MX MXPA02008228A patent/MXPA02008228A/es unknown
- 2001-02-22 HU HU0300212A patent/HUP0300212A2/hu unknown
- 2001-02-22 IL IL15105901A patent/IL151059A0/xx unknown
- 2001-02-22 WO PCT/DK2001/000123 patent/WO2001043525A2/en not_active Application Discontinuation
- 2001-02-22 AU AU2001235358A patent/AU2001235358A1/en not_active Abandoned
- 2001-02-22 BR BR0108937-4A patent/BR0108937A/pt not_active IP Right Cessation
- 2001-02-22 KR KR1020027011111A patent/KR20020081355A/ko not_active Application Discontinuation
- 2001-02-22 CN CNA018055567A patent/CN1608057A/zh active Pending
- 2001-02-22 GR GR20010100098A patent/GR1004073B/el unknown
- 2001-02-22 EP EP01907389A patent/EP1259501A2/en not_active Withdrawn
- 2001-02-22 EA EA200200898A patent/EA005315B1/ru not_active IP Right Cessation
- 2001-02-22 PL PL01363119A patent/PL363119A1/xx not_active Application Discontinuation
- 2001-02-22 JP JP2001544478A patent/JP2003523955A/ja not_active Withdrawn
- 2001-02-22 CA CA002401236A patent/CA2401236A1/en not_active Abandoned
- 2001-02-22 IE IE20010163A patent/IES20010163A2/en not_active IP Right Cessation
- 2001-02-23 AR ARP010100836A patent/AR029658A1/es not_active Application Discontinuation
- 2001-02-23 BE BE2001/0126A patent/BE1011177A6/fr not_active IP Right Cessation
- 2001-02-26 US US09/794,762 patent/US6420574B2/en not_active Expired - Lifetime
- 2001-02-26 IT IT2001MI000386A patent/ITMI20010386A1/it unknown
-
2002
- 2002-07-29 IS IS6487A patent/IS6487A/is unknown
- 2002-08-09 HR HRP20020660 patent/HRP20020660A2/hr not_active Application Discontinuation
- 2002-08-19 NO NO20023928A patent/NO20023928D0/no not_active Application Discontinuation
- 2002-09-04 BG BG107061A patent/BG107061A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL1017415C1 (nl) | 2001-05-18 |
| WO2001043525A3 (en) | 2002-01-31 |
| NO20023928L (no) | 2002-08-19 |
| IS6487A (is) | 2002-07-29 |
| IES20010163A2 (en) | 2002-03-06 |
| EA005315B1 (ru) | 2004-12-30 |
| MXPA02008228A (es) | 2004-04-05 |
| NO20023928D0 (no) | 2002-08-19 |
| SK13672002A3 (sk) | 2003-03-04 |
| US6420574B2 (en) | 2002-07-16 |
| BE1011177A6 (fr) | 2001-07-03 |
| BG107061A (en) | 2003-05-30 |
| WO2001043525A2 (en) | 2001-06-21 |
| FR2805812A1 (fr) | 2001-09-07 |
| JP2003523955A (ja) | 2003-08-12 |
| IL151059A0 (en) | 2003-04-10 |
| AR029658A1 (es) | 2003-07-10 |
| GR1004073B (el) | 2002-11-26 |
| ITMI20010386A1 (it) | 2002-08-26 |
| CN1608057A (zh) | 2005-04-20 |
| GR20010100098A (el) | 2001-10-31 |
| BR0108937A (pt) | 2003-06-17 |
| EA200200898A1 (ru) | 2003-02-27 |
| CA2401236A1 (en) | 2001-06-21 |
| KR20020081355A (ko) | 2002-10-26 |
| EP1259501A2 (en) | 2002-11-27 |
| PL363119A1 (en) | 2004-11-15 |
| US20010027256A1 (en) | 2001-10-04 |
| HRP20020660A2 (en) | 2004-12-31 |
| AU2001235358A1 (en) | 2001-06-25 |
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