HRP20110636T1 - Postupak za dobijanje escitaloprama - Google Patents
Postupak za dobijanje escitaloprama Download PDFInfo
- Publication number
- HRP20110636T1 HRP20110636T1 HR20110636T HRP20110636T HRP20110636T1 HR P20110636 T1 HRP20110636 T1 HR P20110636T1 HR 20110636 T HR20110636 T HR 20110636T HR P20110636 T HRP20110636 T HR P20110636T HR P20110636 T1 HRP20110636 T1 HR P20110636T1
- Authority
- HR
- Croatia
- Prior art keywords
- hydroxybutyl
- fluorophenyl
- hydroxymethyl
- benzonitrile
- dimethylamino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 24
- WSEQXVZVJXJVFP-FQEVSTJZSA-N escitalopram Chemical compound C1([C@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-FQEVSTJZSA-N 0.000 title claims 4
- 229960004341 escitalopram Drugs 0.000 title claims 4
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000002904 solvent Substances 0.000 claims abstract 14
- RVGFHORHCHHPCZ-UHFFFAOYSA-N 4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile;hydrobromide Chemical compound Br.C=1C=C(C#N)C=C(CO)C=1C(O)(CCCN(C)C)C1=CC=C(F)C=C1 RVGFHORHCHHPCZ-UHFFFAOYSA-N 0.000 claims abstract 11
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims abstract 9
- 150000003839 salts Chemical class 0.000 claims abstract 7
- 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 class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract 5
- 239000000203 mixture Substances 0.000 claims abstract 4
- 238000001640 fractional crystallisation Methods 0.000 claims abstract 2
- 239000002253 acid Substances 0.000 claims 4
- OGODKNYCTJYXFF-HZPDHXFCSA-N bis(4-methylbenzoyl) (2r,3r)-2,3-dihydroxybutanedioate Chemical compound C1=CC(C)=CC=C1C(=O)OC(=O)[C@H](O)[C@@H](O)C(=O)OC(=O)C1=CC=C(C)C=C1 OGODKNYCTJYXFF-HZPDHXFCSA-N 0.000 claims 4
- 238000001816 cooling Methods 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 238000010992 reflux Methods 0.000 claims 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- OGODKNYCTJYXFF-HOTGVXAUSA-N bis(4-methylbenzoyl) (2s,3s)-2,3-dihydroxybutanedioate Chemical compound C1=CC(C)=CC=C1C(=O)OC(=O)[C@@H](O)[C@H](O)C(=O)OC(=O)C1=CC=C(C)C=C1 OGODKNYCTJYXFF-HOTGVXAUSA-N 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000012452 mother liquor Substances 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 230000000707 stereoselective effect Effects 0.000 claims 1
- 230000009466 transformation Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 238000000926 separation method Methods 0.000 abstract 1
Classifications
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- 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
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/53—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton
Abstract
Postupak za razdvajanje 4-[4-(dimetilamino)-1-(4'-fluorofenil)-1-hidroksibutil]-3-(hidroksimetil)-benzonitrila u obliku racemske ili neracemske smjese enantiomera na njegove izolirane enantiomere, naznačen time, što spomenuti postupak sadrži korak frakcijske kristalizacije 4-[4-(dimetilamino)-1-(4'-fluorofenil)-1-hidroksibutil]-3-(hidroksimetil)-benzonitrila u obliku soli sa (+)-(S,S) ili (-)-(R,R)-enantiomerom O,O'-di-p-toluoil-vinske kiseline u sustavu otapala, pri čemu 1-propanol sačinjava najmanje 50% sustava otapala. Patent sadrži još 18 patentnih zahtjeva.
Claims (19)
1. Postupak za razdvajanje 4-[4-(dimetilamino)-1-(4'-fluorofenil)-1-hidroksibutil]-3-(hidroksimetil)-benzonitrila u obliku racemske ili neracemske smjese enantiomera na njegove izolirane enantiomere, naznačen time, što spomenuti postupak sadrži korak frakcijske kristalizacije 4-[4-(dimetilamino)-1-(4'-fluorofenil)-1-hidroksibutil]-3-(hidroksimetil)-benzonitrila u obliku soli sa (+)-(S,S) ili (-)-(R,R)-enantiomerom O,O’-di-p-toluoil-vinske kiseline u sustavu otapala, pri čemu 1-propanol sačinjava najmanje 50% sustava otapala.
2. Postupak prema zahtjevu 1, naznačen time što se ne upotrebljava više od 1 mol (+)-(S,S) ili (-)-(R,R)-enantiomera O,O’-di-p-toluoil-vinske kiseline po molu 4-[4-(dimetilamino)-1-(4’-fluorofenil)-1-hidroksibutil]-3-(hidroksimetil)-benzonitrila.
3. Postupak prema zahtjevu 1 ili 2, naznačen time što se upotrebljava (+)-O,O’-di-p-toluoil-(S,S)-vinska kiselina.
4. Postupak prema zahtjevu 1 ili 2, naznačen time, što se upotrebljava (-)-O,O’-di-p-toluoil- (R,R)-vinska kiselina.
5. Postupak prema bilo kojem od zahtjeva 1-4, naznačen time što sustav otapala sadrži jedan ili više organskih kootapala.
6. Postupak prema bilo kojem od zahtjeva 1-5, naznačen time što sustav otapala sadrži vodu.
7. Postupak prema bilo kojem od zahtjeva 1-6, naznačen time što sustav otapala sadrži ahiralnu kiselinu koja može protonirati 4-[4-(dimetil-amino)-1-(4'-fluorofenil)-1-hidroksibutil]-3-(hidroksimetil)-benzonitril, ali ne može istaložiti 4-[4-(dimetilamino)-1-(4'-fluorofenil)-1-hidroksibutil]-3-(hidroksimetil)-benzonitril u obliku soli u aktuelnim uvjetima.
8. Postupak prema zahtjevu 7, naznačen time što je ahiralna kiselina izabrana iz grupe koja se sastoji od organskih kiselina.
9. Postupak prema bilo kojem od zahtjeva 1-8, naznačen time što se sustav otapala zajedno sa otopljenim 4-[4-(dimetilamino)-1-(4'-fluorofenil)-1-hidroksibutil]-3-(hidroksimetil)-benzonitrilom i (+)-(S,S)- ili (-)-(R,R)-O,O’-di-p-toluoil-vinskom kiselinom hladi sa prve temperature u opsegu od do temperature refluksa za sustav otapala na drugu temperaturu u opsegu od do .
10. Postupak prema zahtjevu 10, naznačen time što se smjesa 4-[4-(dimetilamino)-1-(4'-fluorofenil)-1-hidroksibutil]-3-(hidroksimetil)-benzonitrila, (+)-(S,S)- ili (-)-(R,R)-O,O’-di-p-toluoil-vinske kiseline i sustava otapala održava na prvoj temperaturi tokom perioda u opsegu od 0-4 sati prije hlađenja.
11. Postupak prema zahtjevu 9 ili 10, naznačen time što se smjesa 4-[4-(dimetilamino)-1-(4'-fluorofenil)-1-hidroksibutil]-3-(hidroksimetil)-benzonitrila, (+)-(S,S)- ili (-)-(R,R)-O,O’-di-p-toluoil-vinske kiseline i sustava otapala zasijava kristalima željene soli na prvoj temperaturi ili tokom hlađenja.
12. Postupak prema bilo kojem od zahtjeva 9-11, naznačen time što se hlađenje vrši tokom 8 sati.
13. Postupak prema bilo kojem od zahtjeva 1-12, naznačen time što se istaložena sol izdvaja iz matične lužine tokom 8 sati poslije početka taloženja.
14. Postupak prema bilo kojem od zahtjeva 1-13, naznačen time što se izdvojena sol ispire tokom 4 sata.
15. Postupak prema bilo kojem od zahtjeva 1-14, naznačen time što se izdvojena sol ponovo suspendira ili rekristalizira jednom ili više puta u sustavu otapala koji sadrži 1-propanol ili etanol zagrijanjem do temperature u opsegu od do temperature refluksa otapala.
16. Postupak za dobijanje escitaloprama, naznačen time što sadrži postupak prema bilo kojem od zahtjeva 1-15.
17. Postupak prema zahtjevu 16, naznačen time što sadrži stereoselektivnu transformaciju jednog od izoliranih enantiomera 4-[4-(dimetilamino)-1-(4'-fluorofenil)-1-hidroksibutil]-3-(hidroksimetil)-benzonitrila u escitalopram.
18. Postupak prema zahtjevu 17, naznačen time što se S-4-[4-(dimetilamino)-1-(4'-fluorofenil)-1-hidroksibutil]-3-(hidroksimetil)-benzonitril stereoselektivno transformira u escitalopram.
19. Postupak prema zahtjevu 18, naznačen time, što S-4-[4-(dimetilamino)-1-(4'-fluorofenil)-1-hidroksibutil]-3-(hidroksimetil)-benzonitril reagira sa derivatom reaktivne kiseline kao što je kiseli klorid ili kiseli anhidrid, u prisustvu baze.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200701314 | 2007-09-11 | ||
| PCT/DK2008/050222 WO2009033488A1 (en) | 2007-09-11 | 2008-09-10 | Method for manufacture of escitalopram |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20110636T1 true HRP20110636T1 (hr) | 2011-10-31 |
Family
ID=39735675
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20080425A HRP20080425A2 (hr) | 2007-09-11 | 2008-09-02 | Postupak za proizvodnju escitaloprama |
| HR20110636T HRP20110636T1 (hr) | 2007-09-11 | 2011-09-07 | Postupak za dobijanje escitaloprama |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20080425A HRP20080425A2 (hr) | 2007-09-11 | 2008-09-02 | Postupak za proizvodnju escitaloprama |
Country Status (52)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007012954A1 (en) | 2005-07-27 | 2007-02-01 | Aurobindo Pharma Limited | An improved process for the preparation of escitalopram |
| CN102796065A (zh) * | 2011-05-27 | 2012-11-28 | 江苏豪森医药集团连云港宏创医药有限公司 | 一种制备光学纯度高的艾司西酞普兰的方法 |
| CN104119240A (zh) * | 2013-04-23 | 2014-10-29 | 中国人民解放军军事医学科学院毒物药物研究所 | (S)-(-)-α-甲胺基苯丙酮的制备方法 |
| CN103497145B (zh) * | 2013-10-10 | 2016-01-27 | 南昌大学 | 一种光学纯多奈哌齐的制备工艺 |
| CN104119248A (zh) * | 2014-08-08 | 2014-10-29 | 广东东阳光药业有限公司 | S-西酞普兰的制备方法 |
| WO2016074225A1 (zh) * | 2014-11-14 | 2016-05-19 | 浙江华海药业股份有限公司 | 一种拆分西酞普兰中间体5-氰二醇的方法 |
Family Cites Families (9)
| 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 (es) | 2001-06-25 | 2004-03-03 | Lundbeck & Co As H | Proceso para la preparacion del citalopram racemico y/o del s- o r-citalopram mediante la separacion de una mezcla de r- y s-citalopram |
| AR034759A1 (es) * | 2001-07-13 | 2004-03-17 | Lundbeck & Co As H | Metodo para la preparacion de escitalopram |
| IS7239A (is) * | 2001-12-14 | 2004-04-29 | H. Lundbeck A/S | Aðferð til framleiðslu á essítalóprami |
| JP4505335B2 (ja) | 2002-12-23 | 2010-07-21 | ハー・ルンドベック・アクチエゼルスカベット | ラセミ体シタロプラムジオール（ｒａｃｅｍｉｃｃｉｔａｌｏｐｒａｍｄｉｏｌ）および／またはＳ−もしくはＲ−シタロプラムジオールの製造方法、およびラセミ体シタロプラム、Ｒ−シタロプラムおよび／またはＳ−シタロプラムを製造するために、上記ジオールを使用する方法。 |
| AU2003242990A1 (en) * | 2003-01-17 | 2004-08-13 | Pulla Reddy Muddasani | Processes for the preparation of escitalopram and its precursor |
| US20090018351A1 (en) * | 2003-11-12 | 2009-01-15 | Dr. Reddy's Laboratories, Inc. | Preparation of escitalopram |
| EP1877394A1 (en) * | 2005-04-04 | 2008-01-16 | Jubilant Organosys Limited | Process for the preparation of escitalopram or its acid addition salts |
| WO2007012954A1 (en) * | 2005-07-27 | 2007-02-01 | Aurobindo Pharma Limited | An improved process for the preparation of escitalopram |
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2008
- 2008-08-29 FI FI20085807A patent/FI121570B/fi not_active IP Right Cessation
- 2008-08-29 NZ NZ570884A patent/NZ570884A/en not_active IP Right Cessation
- 2008-09-01 IE IE20080708A patent/IES20080708A2/en not_active IP Right Cessation
- 2008-09-01 TW TW097133379A patent/TWI391383B/zh active
- 2008-09-01 NO NO20083756A patent/NO20083756L/no unknown
- 2008-09-01 GB GB0815773A patent/GB2448848B/en not_active Expired - Fee Related
- 2008-09-02 IL IL193845A patent/IL193845A/en active IP Right Grant
- 2008-09-02 HR HR20080425A patent/HRP20080425A2/hr not_active Application Discontinuation
- 2008-09-02 BG BG110206A patent/BG110206A/en unknown
- 2008-09-02 LV LVP-08-154A patent/LV13813B/lv unknown
- 2008-09-02 IS IS8758A patent/IS8758A/is unknown
- 2008-09-02 EA EA200801797A patent/EA012787B1/ru not_active IP Right Cessation
- 2008-09-02 JP JP2008224435A patent/JP4966933B2/ja active Active
- 2008-09-03 LT LT2008068A patent/LT5577B/lt not_active IP Right Cessation
- 2008-09-03 ME MEP-2008-101A patent/ME00176B/me unknown
- 2008-09-03 AR ARP080103832A patent/AR068174A1/es active IP Right Grant
- 2008-09-04 CZ CZ20080537A patent/CZ2008537A3/cs unknown
- 2008-09-04 RS RSP-2008/0401A patent/RS20080401A/sr unknown
- 2008-09-04 MY MYPI20083415A patent/MY144210A/en unknown
- 2008-09-04 PL PL386026A patent/PL386026A1/pl unknown
- 2008-09-04 NL NL2001953A patent/NL2001953C2/en not_active IP Right Cessation
- 2008-09-05 HU HU0800549A patent/HUP0800549A2/hu unknown
- 2008-09-05 SI SI200800207A patent/SI22567A2/sl not_active IP Right Cessation
- 2008-09-08 MX MX2008011451A patent/MX2008011451A/es active IP Right Grant
- 2008-09-08 AU AU2008212055A patent/AU2008212055C1/en active Active
- 2008-09-09 PT PT104169A patent/PT104169A/pt not_active IP Right Cessation
- 2008-09-09 EE EEU200800091U patent/EE00864U1/xx not_active IP Right Cessation
- 2008-09-09 SE SE0801929A patent/SE533041C2/sv not_active IP Right Cessation
- 2008-09-09 ZA ZA200807753A patent/ZA200807753B/en unknown
- 2008-09-10 PT PT08801398T patent/PT2061753E/pt unknown
- 2008-09-10 ES ES08801398T patent/ES2368294T3/es active Active
- 2008-09-10 SG SG200806650-8A patent/SG151195A1/en unknown
- 2008-09-10 DE DE102008046530A patent/DE102008046530A1/de not_active Withdrawn
- 2008-09-10 PL PL08801398T patent/PL2061753T3/pl unknown
- 2008-09-10 CY CY0800015A patent/CY2600B1/xx unknown
- 2008-09-10 EP EP11172640A patent/EP2397461A1/en not_active Withdrawn
- 2008-09-10 CL CL2008002686A patent/CL2008002686A1/es unknown
- 2008-09-10 UA UAU200811050U patent/UA43461U/uk unknown
- 2008-09-10 WO PCT/DK2008/050222 patent/WO2009033488A1/en active Application Filing
- 2008-09-10 RS RS20110394A patent/RS51909B/en unknown
- 2008-09-10 GR GR20080100581A patent/GR1006595B/el not_active IP Right Cessation
- 2008-09-10 AT AT08801398T patent/ATE518829T1/de active
- 2008-09-10 SK SK50030-2008A patent/SK500302008A3/sk unknown
- 2008-09-10 UA UAU200901635U patent/UA41919U/uk unknown
- 2008-09-10 CO CO08095718A patent/CO6140012A1/es not_active Application Discontinuation
- 2008-09-10 CA CA2638499A patent/CA2638499C/en not_active Expired - Fee Related
- 2008-09-10 CN CNA2008101686272A patent/CN101386583A/zh active Pending
- 2008-09-10 EP EP08801398A patent/EP2061753B1/en active Active
- 2008-09-10 ES ES200802582A patent/ES2334875B1/es not_active Expired - Fee Related
- 2008-09-10 FR FR0856077A patent/FR2920766A1/fr active Pending
- 2008-09-10 DK DK08801398.2T patent/DK2061753T3/da active
- 2008-09-10 SI SI200830361T patent/SI2061753T1/sl unknown
- 2008-09-10 DK DKPA200801265A patent/DK177075B1/da not_active IP Right Cessation
- 2008-09-11 TR TR2009/07629A patent/TR200907629A2/xx unknown
- 2008-09-11 LU LU91479A patent/LU91479B1/fr active
- 2008-09-11 TR TR2008/06903A patent/TR200806903A2/xx unknown
- 2008-09-11 BR BRPI0804121-0A patent/BRPI0804121B1/pt active IP Right Grant
- 2008-09-11 KR KR1020080090058A patent/KR101054224B1/ko active IP Right Grant
- 2008-09-11 AT AT0048708U patent/AT10984U1/de not_active IP Right Cessation
- 2008-09-11 RO ROA200800706A patent/RO125301A2/ro unknown
- 2008-09-11 BE BE2008/0498A patent/BE1017548A6/fr not_active IP Right Cessation
- 2008-09-11 CH CH01450/08A patent/CH697885B1/de not_active IP Right Cessation
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2011
- 2011-09-07 HR HR20110636T patent/HRP20110636T1/hr unknown
- 2011-10-07 CY CY20111100963T patent/CY1111924T1/el unknown
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2017
- 2017-06-26 AR ARP170101761A patent/AR108885A2/es unknown
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