WO2015044963A1 - An amorphous vortioxetine and salts thereof - Google Patents

An amorphous vortioxetine and salts thereof Download PDF

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Publication number
WO2015044963A1
WO2015044963A1 PCT/IN2014/000633 IN2014000633W WO2015044963A1 WO 2015044963 A1 WO2015044963 A1 WO 2015044963A1 IN 2014000633 W IN2014000633 W IN 2014000633W WO 2015044963 A1 WO2015044963 A1 WO 2015044963A1
Authority
WO
WIPO (PCT)
Prior art keywords
vortioxetine
amorphous
less
hydrobromide
vortioxetine hydrobromide
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/IN2014/000633
Other languages
English (en)
French (fr)
Other versions
WO2015044963A9 (en
Inventor
Shri Prakash Dhar Dwivedi
Brij Khera
Kumar Kamlesh SINGH
Jitendra Maganbhai Gajera
Dinesh Kumar RAIKWAR
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Zydus Lifesciences Ltd
Original Assignee
Cadila Healthcare Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cadila Healthcare Ltd filed Critical Cadila Healthcare Ltd
Priority to US14/916,075 priority Critical patent/US10414741B2/en
Publication of WO2015044963A1 publication Critical patent/WO2015044963A1/en
Publication of WO2015044963A9 publication Critical patent/WO2015044963A9/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • 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
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/36—Opioid-abuse

Definitions

  • the field of the invention relates to an amorphous vortioxetine and salts thereof.
  • the invention relates to a process for the preparation of an amorphous vortioxetine hydrobromide.
  • the invention also relates to a process for preparation of amorphous vortioxetine free base.
  • the invention also relates to pharmaceutical compositions comprising an amorphous vortioxetine or hydrobromide salt thereof for oral administration for treatment of major depressive disorder (MDD) and generalized anxiety disorder (GAD).
  • MDD major depressive disorder
  • GAD generalized anxiety disorder
  • amorphous vortioxetine or salts thereof and hydrates thereof is at least stable under ordinary stability conditions with respect to purity, storage and is free flowing powder.
  • the amorphous vortioxetine hydrobromide having a purity by HPLC of greater than 98% and residual solvent less than 0.5%.
  • Step b) involves removal of the solvent to obtain an amorphous vortioxetine hydrobromide.
  • the isolation may be affected by removing solvent.
  • Techniques which may be used for the removal of solvent include distillation, distillation under vacuum, spray drying, agitated thin film dyring ("ATFD”), and freeze drying (lyophilization).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Psychiatry (AREA)
  • Medicinal Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Addiction (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
PCT/IN2014/000633 2013-09-30 2014-09-30 An amorphous vortioxetine and salts thereof Ceased WO2015044963A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US14/916,075 US10414741B2 (en) 2013-09-30 2014-09-30 Amorphous vortioxetine and salts thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN3121/MUM/2013 2013-09-30
IN3121MU2013 IN2013MU03121A (enExample) 2013-09-30 2014-09-30

Publications (2)

Publication Number Publication Date
WO2015044963A1 true WO2015044963A1 (en) 2015-04-02
WO2015044963A9 WO2015044963A9 (en) 2015-05-07

Family

ID=52117938

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2014/000633 Ceased WO2015044963A1 (en) 2013-09-30 2014-09-30 An amorphous vortioxetine and salts thereof

Country Status (3)

Country Link
US (1) US10414741B2 (enExample)
IN (1) IN2013MU03121A (enExample)
WO (1) WO2015044963A1 (enExample)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016116077A1 (en) * 2015-01-21 2016-07-28 Zentiva, K.S. Polymer-stabilized amorphous forms of vortioxetine
WO2016125190A2 (en) 2015-02-04 2016-08-11 Mylan Laboratories Limited Novel crystalline forms of vortioxetine, premixes, and processes for the preparation thereof
CN106491604A (zh) * 2015-09-07 2017-03-15 常州方楠医药技术有限公司 一种无定型沃替西汀或其盐与药用辅料的组合物及其制备方法
WO2017041680A1 (zh) * 2015-09-07 2017-03-16 常州方楠医药技术有限公司 一种沃替西汀或其盐的药用组合物及其制备方法
WO2017045655A1 (en) * 2015-09-16 2017-03-23 Zentiva, K.S. An amorphous form of vortioxetine hydrobromide stabilized by a cyclodextrin
CN106556663A (zh) * 2015-09-30 2017-04-05 成都弘达药业有限公司 一种1-[2-(2,4-二甲基苯基硫烷基)苯基]哌嗪或其盐的检测方法
WO2017125504A1 (en) * 2016-01-20 2017-07-27 Amneal Pharmaceuticals Company Gmbh Polymorphic forms of vortioxetine hydrobromide tert-butanolate
WO2018042168A1 (en) * 2016-08-29 2018-03-08 King, Lawrence Stable pharmaceutical composition of vortioxetine hydrobromide
WO2018150344A1 (en) 2017-02-17 2018-08-23 Unichem Laboratories Ltd Bioequivalent pharmaceutical composition of vortioxetine hydrobromide
US10519121B2 (en) 2016-12-30 2019-12-31 Apicore Us Llc Process and novel polymorphic form of vortioxetine and its pharmaceutically acceptable salts
WO2021043227A1 (zh) * 2019-09-04 2021-03-11 普济生物科技（台州）有限公司 用于口腔掩味的含氢溴酸沃替西汀的包衣颗粒、固体分散体和制剂
WO2021150188A1 (en) * 2020-01-23 2021-07-29 Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi Crystalline form c of vortioxetine hydrobromide
WO2025132869A1 (en) * 2023-12-21 2025-06-26 H. Lundbeck A/S Method for the preparation of vortioxetine pharmaceutical compositions with low amounts of nitrosamine impurities
JP2025109162A (ja) * 2024-01-11 2025-07-24 Cbc株式会社 ボルチオキセチン臭化水素酸塩の非晶質体からなる固形物

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106518807A (zh) * 2016-09-17 2017-03-22 北京万全德众医药生物技术有限公司 乳酸沃替西汀晶型的制备方法
WO2020087031A1 (en) 2018-10-26 2020-04-30 The Research Foundation For The State University Of New York Combination serotonin specific reuptake inhibitor and serotonin 1a receptor partial agonist for reducing l-dopa-induced dyskinesia
CN112830906B (zh) * 2020-12-31 2022-05-13 微研优仿医药科技(江苏)有限公司 一种伏硫西汀氢溴酸盐α晶型的制备方法
CN113143886A (zh) * 2021-05-07 2021-07-23 苏州康恒研新药物技术有限公司 一种氢溴酸伏硫西汀微丸缓释制剂的制备方法
CN115160258B (zh) * 2022-06-24 2023-11-17 辰欣药业股份有限公司 一种氢溴酸沃替西汀γ晶型的制备方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003029232A1 (en) 2001-10-04 2003-04-10 H. Lundbeck A/S Phenyl-piperazine derivatives as serotonin reuptake inhibitors
WO2007144005A1 (en) * 2006-06-16 2007-12-21 H. Lundbeck A/S 1- [2- (2, 4-dimethylphenylsulfanyl) -phenyl] piperazine as a compound with combined serotonin reuptake, 5-ht3 and 5-ht1a activity for the treatment of cognitive impairment
WO2010094285A1 (en) * 2009-02-17 2010-08-26 H. Lundbeck A/S Purification of 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine
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
WO2014177491A1 (en) * 2013-04-29 2014-11-06 Lek Pharmaceuticals D.D. New solid form of 1-(2-((2,4-dimethylphenyl)thio)phenyl)piperazine hydrobromide

Family Cites Families (3)

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US119521A (en) * 1871-10-03 Improvement in machines for rolling tapering forms
EP2897943B1 (en) * 2012-09-19 2019-04-24 Sandoz AG Crystalline form of vortioxetine hydrobromide
US20170333424A1 (en) * 2014-10-24 2017-11-23 Hexal Ag Amorphous Vortioxetine Hydrobromide

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003029232A1 (en) 2001-10-04 2003-04-10 H. Lundbeck A/S Phenyl-piperazine derivatives as serotonin reuptake inhibitors
US7144884B2 (en) 2001-10-04 2006-12-05 H. Lundbeck A/S Phenyl-piperazine derivatives as serotonin reuptake inhibitors
WO2007144005A1 (en) * 2006-06-16 2007-12-21 H. Lundbeck A/S 1- [2- (2, 4-dimethylphenylsulfanyl) -phenyl] piperazine as a compound with combined serotonin reuptake, 5-ht3 and 5-ht1a activity for the treatment of cognitive impairment
US20100297240A1 (en) 2006-06-16 2010-11-25 H. Lundbeck A/S 1- [2- (2,4-dimethylphenylsulfanyl)-phenyl] piperazine as a compound with combined serotonin reuptake, 5-ht3 and 5-ht1a activity for the treatment of cognitive impairment
WO2010094285A1 (en) * 2009-02-17 2010-08-26 H. Lundbeck A/S Purification of 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine
US20120004409A1 (en) 2009-02-17 2012-01-05 H. Lundbeck A/S Purification of 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine
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
WO2014177491A1 (en) * 2013-04-29 2014-11-06 Lek Pharmaceuticals D.D. New solid form of 1-(2-((2,4-dimethylphenyl)thio)phenyl)piperazine hydrobromide

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
ECONNO T., CHEM. PHARM. BULL., vol. 38, 1990, pages 2003 - 2007

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016116077A1 (en) * 2015-01-21 2016-07-28 Zentiva, K.S. Polymer-stabilized amorphous forms of vortioxetine
WO2016125190A2 (en) 2015-02-04 2016-08-11 Mylan Laboratories Limited Novel crystalline forms of vortioxetine, premixes, and processes for the preparation thereof
WO2016125190A3 (en) * 2015-02-04 2016-09-29 Mylan Laboratories Limited Novel crystalline forms of vortioxetine, premixes, and processes for the preparation thereof
CN106491604A (zh) * 2015-09-07 2017-03-15 常州方楠医药技术有限公司 一种无定型沃替西汀或其盐与药用辅料的组合物及其制备方法
WO2017041680A1 (zh) * 2015-09-07 2017-03-16 常州方楠医药技术有限公司 一种沃替西汀或其盐的药用组合物及其制备方法
WO2017045655A1 (en) * 2015-09-16 2017-03-23 Zentiva, K.S. An amorphous form of vortioxetine hydrobromide stabilized by a cyclodextrin
CN106556663A (zh) * 2015-09-30 2017-04-05 成都弘达药业有限公司 一种1-[2-(2,4-二甲基苯基硫烷基)苯基]哌嗪或其盐的检测方法
WO2017125504A1 (en) * 2016-01-20 2017-07-27 Amneal Pharmaceuticals Company Gmbh Polymorphic forms of vortioxetine hydrobromide tert-butanolate
WO2018042168A1 (en) * 2016-08-29 2018-03-08 King, Lawrence Stable pharmaceutical composition of vortioxetine hydrobromide
US10519121B2 (en) 2016-12-30 2019-12-31 Apicore Us Llc Process and novel polymorphic form of vortioxetine and its pharmaceutically acceptable salts
WO2018150344A1 (en) 2017-02-17 2018-08-23 Unichem Laboratories Ltd Bioequivalent pharmaceutical composition of vortioxetine hydrobromide
WO2021043227A1 (zh) * 2019-09-04 2021-03-11 普济生物科技（台州）有限公司 用于口腔掩味的含氢溴酸沃替西汀的包衣颗粒、固体分散体和制剂
WO2021150188A1 (en) * 2020-01-23 2021-07-29 Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi Crystalline form c of vortioxetine hydrobromide
WO2025132869A1 (en) * 2023-12-21 2025-06-26 H. Lundbeck A/S Method for the preparation of vortioxetine pharmaceutical compositions with low amounts of nitrosamine impurities
JP2025109162A (ja) * 2024-01-11 2025-07-24 Cbc株式会社 ボルチオキセチン臭化水素酸塩の非晶質体からなる固形物

Also Published As

Publication number Publication date
US20160214949A1 (en) 2016-07-28
IN2013MU03121A (enExample) 2015-07-17
WO2015044963A9 (en) 2015-05-07
US10414741B2 (en) 2019-09-17

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