EA201291116A1 - Способ получения метансульфонатных солей ралфинамида или их r-энантиомеров - Google Patents

Способ получения метансульфонатных солей ралфинамида или их r-энантиомеров

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Publication number
EA201291116A1
EA201291116A1 EA201291116A EA201291116A EA201291116A1 EA 201291116 A1 EA201291116 A1 EA 201291116A1 EA 201291116 A EA201291116 A EA 201291116A EA 201291116 A EA201291116 A EA 201291116A EA 201291116 A1 EA201291116 A1 EA 201291116A1
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EA
Eurasian Patent Office
Prior art keywords
water
salt
modification
acetone
carbon atoms
Prior art date
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EA201291116A
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English (en)
Other versions
EA021389B1 (ru
Inventor
Клаудио Джордано
Эрвин Вальдвогель
Original Assignee
Ньюрон Фармасьютикалс С.П.А.
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Application filed by Ньюрон Фармасьютикалс С.П.А. filed Critical Ньюрон Фармасьютикалс С.П.А.
Publication of EA201291116A1 publication Critical patent/EA201291116A1/ru
Publication of EA021389B1 publication Critical patent/EA021389B1/ru

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/04Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C237/08Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/16Amides, e.g. hydroxamic acids
    • A61K31/165Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00Drugs for disorders of the urinary system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00Drugs for genital or sexual disorders; Contraceptives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/04Centrally acting analgesics, e.g. opioids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/06Antimigraine agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/08Antiepileptics; Anticonvulsants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/14Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16Anti-Parkinson drugs
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/18Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/24Antidepressants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/28Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00Preparation of carboxylic acid amides
    • C07C231/22Separation; Purification; Stabilisation; Use of additives
    • C07C231/24Separation; Purification
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/04Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C237/06Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01Sulfonic acids
    • C07C309/02Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/04Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing only one sulfo group

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Pain & Pain Management (AREA)
  • Epidemiology (AREA)
  • Psychiatry (AREA)
  • Hematology (AREA)
  • Urology & Nephrology (AREA)
  • Rheumatology (AREA)
  • Hospice & Palliative Care (AREA)
  • Diabetes (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Obesity (AREA)
  • Psychology (AREA)
  • Cardiology (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Изобретение относится к новому способу получения и/или очистки соли соединения (S)-2-[4-(2-фторбензилокси)бензиламино]пропанамида, то есть ралфинамида, или соответственного R-энантиомера, и метансульфокислоты с высокими выходами и очень высокими энантиомерной и химической степенями чистоты в форме кристаллической безводной полиморфной модификации, идентифицируемой как форма А, где упомянутая соль является в значительной мере свободной от примесей, имеющих генотоксический эффект, таких как (C-C)алканилметансульфонаты, и от остаточных растворителей, известных как их потенциальные вещества-предшественники, таких как (C-C)алканолы или сложные эфиры алканолов и низших алкановых кислот. Способ предусматривает (i) получение и/или кристаллизацию соли из воды, ацетона, алифатического кетона с 4-5 атомами углерода или из их смеси с водой, или (ii) суспендирование твердой соли (а) с водой, (b) со смесью воды с ацетоном или с алифатическим кетоном с 4-5 атомами углерода, (с) с ацетоном, алифатическим кетоном с 4-5 атомами углерода или с их смесью, или (iii) воздействие на твердую соль потока воздуха, имеющего высокую степень относительной влажности, и в том случае, когда полученный продукт состоит полностью или частично из кристаллов с кристаллической полугидратной псевдополиморфной модификацией формы Н, превращение упомянутого продукта в кристаллы безводной формы А путем проведения процесса удаления воды. Кристаллическая полугидратная псевдополиморфная модификация формы Н метансульфоната ралфинамида или его R-энантиомера является полезным промежуточным соединением для получения кристаллической безводной полиморфной модификации формы А, свободной от
EA201291116A 2010-04-27 2011-04-06 Способ получения метансульфонатных солей ралфинамида или их r-энантиомеров EA021389B1 (ru)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP10161207 2010-04-27
PCT/EP2011/055309 WO2011134763A1 (en) 2010-04-27 2011-04-06 Process for the production of ralfinamide methanesulfonate salts or their r-enantiomers

Publications (2)

Publication Number Publication Date
EA201291116A1 true EA201291116A1 (ru) 2013-04-30
EA021389B1 EA021389B1 (ru) 2015-06-30

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Application Number Title Priority Date Filing Date
EA201291116A EA021389B1 (ru) 2010-04-27 2011-04-06 Способ получения метансульфонатных солей ралфинамида или их r-энантиомеров

Country Status (28)

Country Link
US (2) US9505708B2 (ru)
EP (1) EP2563355B1 (ru)
JP (3) JP5808392B2 (ru)
KR (1) KR101851118B1 (ru)
CN (2) CN102858330B (ru)
AR (1) AR085171A1 (ru)
AU (1) AU2011246707B2 (ru)
BR (1) BR112012027623B1 (ru)
CA (1) CA2794389C (ru)
CY (1) CY1117879T1 (ru)
DK (1) DK2563355T3 (ru)
EA (1) EA021389B1 (ru)
ES (1) ES2590128T3 (ru)
HK (2) HK1179881A1 (ru)
HR (1) HRP20161077T1 (ru)
HU (1) HUE030504T2 (ru)
IL (1) IL222532A (ru)
LT (1) LT2563355T (ru)
ME (1) ME02509B (ru)
MX (1) MX342697B (ru)
NZ (2) NZ602648A (ru)
PL (1) PL2563355T3 (ru)
PT (1) PT2563355T (ru)
RS (1) RS55084B1 (ru)
SI (1) SI2563355T1 (ru)
SM (1) SMT201600266B (ru)
TW (1) TWI492919B (ru)
WO (1) WO2011134763A1 (ru)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2011246707B2 (en) * 2010-04-27 2014-11-20 Newron Pharmaceuticals S.P.A. Process for the production of ralfinamide methanesulfonate salts or their R-enantiomers
CN103804341B (zh) * 2012-11-13 2018-04-10 中国人民解放军军事医学科学院毒物药物研究所 酰胺衍生物及其医药用途
CN104761531B (zh) * 2014-01-03 2017-12-01 中国人民解放军军事医学科学院毒物药物研究所 镇痛活性化合物及其医药用途
CN104292128A (zh) * 2014-07-01 2015-01-21 南京正科制药有限公司 一种沙芬酰胺晶型a
CN115368310A (zh) * 2021-05-18 2022-11-22 奥库菲尔医药公司 合成甲磺酸酚妥拉明的方法

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AU2011246707B2 (en) * 2010-04-27 2014-11-20 Newron Pharmaceuticals S.P.A. Process for the production of ralfinamide methanesulfonate salts or their R-enantiomers

Also Published As

Publication number Publication date
CA2794389C (en) 2016-08-23
US9505708B2 (en) 2016-11-29
JP2013528577A (ja) 2013-07-11
EA021389B1 (ru) 2015-06-30
CN105037188B (zh) 2017-06-23
RS55084B1 (sr) 2016-12-30
CA2794389A1 (en) 2011-11-03
JP2017197553A (ja) 2017-11-02
BR112012027623B1 (pt) 2021-07-06
HK1213872A1 (zh) 2016-07-15
US20170029365A1 (en) 2017-02-02
ME02509B (me) 2017-02-20
NZ602648A (en) 2014-10-31
CN102858330B (zh) 2015-07-22
HUE030504T2 (en) 2017-05-29
CN102858330A (zh) 2013-01-02
ES2590128T3 (es) 2016-11-18
WO2011134763A1 (en) 2011-11-03
JP5808392B2 (ja) 2015-11-10
DK2563355T3 (en) 2016-09-12
CN105037188A (zh) 2015-11-11
JP6345154B2 (ja) 2018-06-20
SMT201600266B (it) 2016-08-31
US9856207B2 (en) 2018-01-02
MX2012012093A (es) 2012-12-17
EP2563355B1 (en) 2016-06-08
SI2563355T1 (sl) 2016-10-28
CY1117879T1 (el) 2017-05-17
IL222532A (en) 2017-09-28
AR085171A1 (es) 2013-09-18
IL222532A0 (en) 2012-12-31
US20130039983A1 (en) 2013-02-14
AU2011246707B2 (en) 2014-11-20
TW201139344A (en) 2011-11-16
EP2563355A1 (en) 2013-03-06
KR20130094212A (ko) 2013-08-23
TWI492919B (zh) 2015-07-21
MX342697B (es) 2016-10-10
KR101851118B1 (ko) 2018-04-23
JP6450420B2 (ja) 2019-01-09
HK1179881A1 (en) 2013-10-11
NZ700221A (en) 2016-04-29
LT2563355T (lt) 2016-09-26
PT2563355T (pt) 2016-09-02
BR112012027623A2 (pt) 2016-08-09
HRP20161077T1 (hr) 2016-10-21
PL2563355T3 (pl) 2016-12-30
JP2015180664A (ja) 2015-10-15

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