AR075436A1 - Produccion y purificacion de 1-[2-(2,4-dimetilfenilsulfanil)fenil] piperazina - Google Patents
Produccion y purificacion de 1-[2-(2,4-dimetilfenilsulfanil)fenil] piperazinaInfo
- Publication number
- AR075436A1 AR075436A1 ARP100100441A ARP100100441A AR075436A1 AR 075436 A1 AR075436 A1 AR 075436A1 AR P100100441 A ARP100100441 A AR P100100441A AR P100100441 A ARP100100441 A AR P100100441A AR 075436 A1 AR075436 A1 AR 075436A1
- Authority
- AR
- Argentina
- Prior art keywords
- piperazine
- dimethylphenylsulfanyl
- phenyl
- hbr
- solution
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 title 2
- 238000000746 purification Methods 0.000 title 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 15
- VNGRUFUIHGGOOM-UHFFFAOYSA-N vortioxetine hydrobromide Chemical compound Br.CC1=CC(C)=CC=C1SC1=CC=CC=C1N1CCNCC1 VNGRUFUIHGGOOM-UHFFFAOYSA-N 0.000 abstract 12
- 239000012453 solvate Substances 0.000 abstract 8
- 239000002904 solvent Substances 0.000 abstract 5
- 238000000034 method Methods 0.000 abstract 4
- 239000002244 precipitate Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- HTZGBJSGEVLJID-UHFFFAOYSA-N 1-[2-(2,4-dimethylphenyl)sulfanylphenyl]piperazine;propan-2-ol;hydrobromide Chemical compound Br.CC(C)O.CC1=CC(C)=CC=C1SC1=CC=CC=C1N1CCNCC1 HTZGBJSGEVLJID-UHFFFAOYSA-N 0.000 abstract 1
- -1 2,4-dimethylphenylsulfanyl Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 239000012535 impurity Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- RYHBGVSBFUOHAE-UHFFFAOYSA-N piperazin-1-ium;bromide Chemical compound Br.C1CNCCN1 RYHBGVSBFUOHAE-UHFFFAOYSA-N 0.000 abstract 1
- 230000001376 precipitating effect Effects 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- YQNWZWMKLDQSAC-UHFFFAOYSA-N vortioxetine Chemical compound CC1=CC(C)=CC=C1SC1=CC=CC=C1N1CCNCC1 YQNWZWMKLDQSAC-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (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)
- Neurology (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Reivindicacion 1: Un proceso para la produccion de de 1-[2-(2,4-dimetilfenilsulfanil)fenil]piperazina o su sal aceptable para uso farmacéutico que comprende el paso de obtener una solucion disolviendo la sal 1-[2-(2,4-dimetilfenilsulfanil)fenil]piperazina-HBr en un solvente que comprende más del 65% (v/v) de isopropanol. Reivindicacion 15: El proceso de acuerdo con la reivindicacion 1 que comprende el paso de a) obtener, una solucion disolviendo 1-[2-(2,4-dimetilfenilsulfanil)fenil]piperazina-HBr en un solvente que comprende más del 65% (v/v) de isopropanol; b) precipitar isopropanol solvato de 1-[2-(2,4-dimetilfenilsulfanil)fenil]piperazina-HBr a partir de dicha solucion obtenida; c) disolver isopropanol solvato de 1-[2-(2,4-dimetilfenilsulfanil)fenil]piperazina-HBr en un solvente que no forma solvatos; y d) precipitar 1-[2-(2,4-dimetilfenilsulfanil)fenil]piperazina-HBr a partir de la solucion obtenida en c). Reivindicacion 19: Un proceso para eliminar o reducir una impureza de la sal 1-[2-(2,4-dimetilfenilsulfanil)fenil]piperazina-HBr solida o una solucion de 1-[2-(2,4-dimetilfenilsulfanil)fenil]piperazina-HBr, comprendiendo el proceso los pasos de: a) mezclar un solvente que comprende más del 65% (v/v) de isopropanol con 1-2-(2,4-dimetilfenilsulfanil)fenil]piperazina-HBr o con una solucion de 1-[2-(2,4-dimetilfenilsulfanil)fenil]piperazina-HBr para obtener una solucion de 1-[2-(2,4-dimetilfenilsulfanil)fenil]piperazina-HBr; y b) enfriar dicha solucion obtenida para precipitar isopropanol solvato de 1-(2-(2,4-dimetilfenilsulfanil)fenil]piperazina-HBr isopropanol solvato; c) disolver isopropanol solvato de 1-[2-(2,4-dimetilfenilsulfanil) fenil]piperazina-HBr, en un solvente que no forma solvatos; y d) precipitar 1-[2-(2,4-dimetilfenilsulfanil)fenil]piperazina-HBr a partir de la solucion que se obtuvo en el paso c). Reivindicacion 22: Un compuestos que es isopropanol solvato de 1-[2-(2,4-dimetilfenilsulfanil)fenil]piperazina-HBr.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200900223 | 2009-02-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR075436A1 true AR075436A1 (es) | 2011-03-30 |
Family
ID=42101395
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP100100441A AR075436A1 (es) | 2009-02-17 | 2010-02-16 | Produccion y purificacion de 1-[2-(2,4-dimetilfenilsulfanil)fenil] piperazina |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US8598348B2 (es) |
| EP (1) | EP2398785B1 (es) |
| JP (1) | JP5738774B2 (es) |
| KR (1) | KR101639833B1 (es) |
| CN (1) | CN102317272B (es) |
| AR (1) | AR075436A1 (es) |
| AU (1) | AU2010214956B2 (es) |
| BR (1) | BRPI1006975B1 (es) |
| CA (1) | CA2751498C (es) |
| CL (1) | CL2011001992A1 (es) |
| CO (1) | CO6400224A2 (es) |
| DK (1) | DK2398785T3 (es) |
| EA (1) | EA020473B1 (es) |
| ES (1) | ES2441079T3 (es) |
| HR (1) | HRP20131236T1 (es) |
| IL (1) | IL214178A (es) |
| MX (1) | MX2011008661A (es) |
| NZ (1) | NZ594658A (es) |
| PL (1) | PL2398785T3 (es) |
| PT (1) | PT2398785E (es) |
| RS (1) | RS53074B (es) |
| SG (1) | SG173735A1 (es) |
| SI (1) | SI2398785T1 (es) |
| SM (1) | SMT201400010B (es) |
| TW (1) | TW201033181A (es) |
| WO (1) | WO2010094285A1 (es) |
| ZA (1) | ZA201105992B (es) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013102573A1 (en) | 2012-01-03 | 2013-07-11 | H. Lundbeck A/S | Process for the manufacture of 1-[2-(2,4-dimethyl-phenylsulfanyl)-phenyl]-piperazine |
| BR112015006075B1 (pt) | 2012-09-19 | 2022-10-04 | Sandoz Ag | Composto cristalino, composição farmacêutica, uso do composto cristalino, hidrato cristalino do bromidrato de vortioxetina, método para a preparação do hidrato cristalino de bromidrato de vortioxetina, método para a preparação do composto cristalino e uso do hidrato cristalino de bromidrato de vortioxetina |
| WO2014090929A1 (en) | 2012-12-13 | 2014-06-19 | H. Lundbeck A/S | Compositions comprising vortioxetine and donepezil |
| UA116236C2 (uk) * | 2013-02-22 | 2018-02-26 | Х. Луннбек А/С | Спосіб одержання вортіоксетину |
| US20160200698A1 (en) | 2013-09-12 | 2016-07-14 | Hangzhou Pushai Pharmaceutical Technology Co., Ltd | Vortioxetine salt and crystal thereof, their preparation method, pharmaceutical compositions and usage |
| IN2013MU03121A (es) | 2013-09-30 | 2015-07-17 | Cadila Healthcare Ltd | |
| EP2878596A1 (en) * | 2013-11-29 | 2015-06-03 | LEK Pharmaceuticals d.d. | Synthesis of vortioxetine via (2-(piperazine-1-yl)phenyl)lithium intermediates |
| CN103788020B (zh) * | 2014-01-22 | 2015-11-04 | 苏州明锐医药科技有限公司 | 沃替西汀的制备方法 |
| CN103788019B (zh) * | 2014-01-22 | 2015-10-07 | 苏州明锐医药科技有限公司 | 沃替西汀的制备方法 |
| EP3099669A1 (en) | 2014-01-31 | 2016-12-07 | Egis Gyógyszergyár Zrt. | Process for the preparation of vortioxetine salts |
| CN104059030B (zh) * | 2014-05-30 | 2016-05-04 | 镇江圣安医药有限公司 | [(苯硫烷基)-苯基]哌嗪的衍生物及其药物组合物和用途 |
| CN105218482B (zh) * | 2014-06-24 | 2018-04-06 | 杭州和泽医药科技有限公司 | 沃替西汀氢溴酸盐β晶型的制备方法 |
| US9687484B2 (en) | 2014-07-18 | 2017-06-27 | Dipharma Francis S.R.L. | Crystalline forms of an antidepressant compound |
| WO2016079751A2 (en) | 2014-11-17 | 2016-05-26 | Megafine Pharma (P) Ltd. | A process for preparation of vortioxetine and polymorphs thereof |
| CN105669594A (zh) * | 2014-11-19 | 2016-06-15 | 康普药业股份有限公司 | 抗抑郁症药1-[2-(2,4-二甲基苯基硫基)苯基]哌嗪的制备方法 |
| CN105801517A (zh) * | 2014-12-30 | 2016-07-27 | 上海奥博生物医药技术有限公司 | 一种沃替西汀氢溴酸盐新晶型及其制备方法 |
| WO2016125190A2 (en) | 2015-02-04 | 2016-08-11 | Mylan Laboratories Limited | Novel crystalline forms of vortioxetine, premixes, and processes for the preparation thereof |
| EP3274330A1 (en) | 2015-03-26 | 2018-01-31 | Cipla Limited | Method for making serotonin reuptake inhibitors |
| CN105367515B (zh) * | 2015-05-08 | 2017-10-27 | 北京北陆药业股份有限公司 | 一种氢溴酸沃替西汀α晶型的制备方法 |
| CN105439980B (zh) * | 2015-05-08 | 2017-10-24 | 北京北陆药业股份有限公司 | 一种氢溴酸沃替西汀一仲丁醇合物及其制备方法 |
| CN106316985B (zh) * | 2015-06-18 | 2021-11-09 | 郑州深蓝海生物医药科技有限公司 | 一种β型高效氢溴酸沃替西汀转晶方法 |
| WO2017125504A1 (en) * | 2016-01-20 | 2017-07-27 | Amneal Pharmaceuticals Company Gmbh | Polymorphic forms of vortioxetine hydrobromide tert-butanolate |
| TW201806599A (zh) | 2016-07-01 | 2018-03-01 | Ｈ 朗德貝克公司 | 用於快速開始抗抑鬱作用之給藥方案 |
| US10519121B2 (en) | 2016-12-30 | 2019-12-31 | Apicore Us Llc | Process and novel polymorphic form of vortioxetine and its pharmaceutically acceptable salts |
| SMT202200073T1 (it) * | 2017-04-25 | 2022-03-21 | H Lundbeck As | Processo per la produzione di vortioxeti-na hbr di forma alfa |
| CN108017595A (zh) * | 2017-12-20 | 2018-05-11 | 安徽源久源科技有限公司 | 一种1-[2-(2,5-二甲基苯硫基)苯基]哌嗪的制备方法 |
| EP3870292A4 (en) | 2018-10-26 | 2022-11-09 | The Research Foundation for The State University of New York | COMBINATION OF SEROTONIN-SPECIFIC RESUPPUT INHIBITOR AND SEROTONIN 1A RECEPTOR PARTIAL AGONIST TO REDUCE L-DOPA-INDUCED DYSKINESIA |
| CN112125868B (zh) * | 2020-09-25 | 2021-08-03 | 中山万远新药研发有限公司 | 一种氢溴酸伏硫西汀晶型及其制备方法、组合物与用途 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB852974A (en) | 1958-04-17 | 1960-11-02 | Parke Davis & Co | Ethers and means for producing the same |
| FR2186237B1 (es) | 1972-05-03 | 1975-10-31 | Synthelabo | |
| US5576460A (en) | 1994-07-27 | 1996-11-19 | Massachusetts Institute Of Technology | Preparation of arylamines |
| UA81749C2 (uk) | 2001-10-04 | 2008-02-11 | Х. Луннбек А/С | Фенілпіперазинові похідні як інгібітори зворотного захоплення серотоніну |
| CA2656057C (en) * | 2006-06-16 | 2012-10-02 | H. Lundbeck A/S | Crystalline forms of 4-[2-(4-methylphenylsulfanyl)-phenyl]piperidine with combined serotonin and norepinephrine reuptake inhibition for the treatment of neuropathic pain |
| ATE540941T1 (de) * | 2006-06-16 | 2012-01-15 | Lundbeck & Co As H | 1-ä2-(2,4-dimethylphenylsulfanyl)phenylüpiperaz n als verbindung mit kombinierter serotoninwiederaufnahme-, 5-ht3- und 5-ht1a- aktivität zur behandlung kognitiver störungen |
| TW200848411A (en) | 2007-03-20 | 2008-12-16 | Lundbeck & Co As H | Novel therapeutic uses of 1-[2-(2, 4-dimethylphenylsulfanyl)phenyl]-piperazine |
-
2010
- 2010-02-04 TW TW099103300A patent/TW201033181A/zh unknown
- 2010-02-16 WO PCT/DK2010/050039 patent/WO2010094285A1/en not_active Ceased
- 2010-02-16 MX MX2011008661A patent/MX2011008661A/es active IP Right Grant
- 2010-02-16 CA CA2751498A patent/CA2751498C/en not_active Expired - Fee Related
- 2010-02-16 NZ NZ594658A patent/NZ594658A/xx not_active IP Right Cessation
- 2010-02-16 ES ES10704890.2T patent/ES2441079T3/es active Active
- 2010-02-16 HR HRP20131236AT patent/HRP20131236T1/hr unknown
- 2010-02-16 CN CN201080007947.5A patent/CN102317272B/zh active Active
- 2010-02-16 US US13/148,088 patent/US8598348B2/en active Active
- 2010-02-16 BR BRPI1006975-5A patent/BRPI1006975B1/pt active IP Right Grant
- 2010-02-16 AR ARP100100441A patent/AR075436A1/es not_active Application Discontinuation
- 2010-02-16 EP EP10704890.2A patent/EP2398785B1/en active Active
- 2010-02-16 SG SG2011059227A patent/SG173735A1/en unknown
- 2010-02-16 SI SI201030444T patent/SI2398785T1/sl unknown
- 2010-02-16 PL PL10704890T patent/PL2398785T3/pl unknown
- 2010-02-16 DK DK10704890.2T patent/DK2398785T3/da active
- 2010-02-16 RS RS20130554A patent/RS53074B/sr unknown
- 2010-02-16 JP JP2011549435A patent/JP5738774B2/ja active Active
- 2010-02-16 KR KR1020117019067A patent/KR101639833B1/ko active Active
- 2010-02-16 EA EA201171065A patent/EA020473B1/ru not_active IP Right Cessation
- 2010-02-16 PT PT107048902T patent/PT2398785E/pt unknown
- 2010-02-16 AU AU2010214956A patent/AU2010214956B2/en active Active
-
2011
- 2011-07-19 IL IL214178A patent/IL214178A/en active IP Right Grant
- 2011-08-05 CO CO11099111A patent/CO6400224A2/es not_active Application Discontinuation
- 2011-08-16 ZA ZA2011/05992A patent/ZA201105992B/en unknown
- 2011-08-16 CL CL2011001992A patent/CL2011001992A1/es unknown
-
2014
- 2014-01-22 SM SM201400010T patent/SMT201400010B/xx unknown
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