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EA201200536A1 - 4r,5s-энантиомер 2-(5-метил-2-оксо-4-фенилпирролидин-1-ил)ацетамида с ноотропной активностью - Google Patents

4r,5s-энантиомер 2-(5-метил-2-оксо-4-фенилпирролидин-1-ил)ацетамида с ноотропной активностью

Info

Publication number
EA201200536A1
EA201200536A1 EA201200536A EA201200536A EA201200536A1 EA 201200536 A1 EA201200536 A1 EA 201200536A1 EA 201200536 A EA201200536 A EA 201200536A EA 201200536 A EA201200536 A EA 201200536A EA 201200536 A1 EA201200536 A1 EA 201200536A1
Authority
EA
Eurasian Patent Office
Prior art keywords
phenylpyrrolidin
methyl
oxo
enantiomer
acetamide
Prior art date
Application number
EA201200536A
Other languages
English (en)
Other versions
EA019890B1 (ru
Inventor
Иварс Калвиньш
Антон Лебедев
Александр Чернобровый
Мая Дамброва
Лига Звейниеце
Максим Ворона
Григорий Вейнберг
Original Assignee
Гриндекс, Джоинт Сток Кампани
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 Гриндекс, Джоинт Сток Кампани filed Critical Гриндекс, Джоинт Сток Кампани
Publication of EA201200536A1 publication Critical patent/EA201200536A1/ru
Publication of EA019890B1 publication Critical patent/EA019890B1/ru

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/4015—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide
    • 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
    • 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
    • A61P25/28—Drugs 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon 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)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Pyrrole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Изобретение относится к 4R,5S-энантиомеру 2-(5-метил-2-оксо-4-фенилпирролидин-1-ил)ацетамида, усиливающему познавательную способность, что имеет большое фармакологическое значение, и к способу получения энантиомера, который включает синтез 5S-метил-4R-фенилпирролидин-2-она, его N-алкилирование этиловым эфиром галоидуксусной кислоты и обработку промежуточного этилового эфира 2-(5S-метил-2-оксо-4R-фенилпирролидин-1-ил)уксусной кислоты аммиаком.
EA201200536A 2009-11-05 2010-11-04 4r,5s-энантиомер 2-(5-метил-2-оксо-4-фенилпирролидин-1-ил)ацетамида с ноотропной активностью EA019890B1 (ru)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
LVP-09-193A LV14346B (lv) 2009-11-05 2009-11-05 2-(4-Fenil-5-metil-2-oksopirolidin-1-il)-acetamīda 4R,5S-enantiomērs ar nootropo aktivitāti
PCT/EP2010/066767 WO2011054888A1 (en) 2009-11-05 2010-11-04 4r,5s-enantiomer of 2-(5-methyl-2-oxo-4-phenyl-pyrrolidin-1-yl)-acetamide with nootropic activity

Publications (2)

Publication Number Publication Date
EA201200536A1 true EA201200536A1 (ru) 2012-09-28
EA019890B1 EA019890B1 (ru) 2014-07-30

Family

ID=43466928

Family Applications (1)

Application Number Title Priority Date Filing Date
EA201200536A EA019890B1 (ru) 2009-11-05 2010-11-04 4r,5s-энантиомер 2-(5-метил-2-оксо-4-фенилпирролидин-1-ил)ацетамида с ноотропной активностью

Country Status (18)

Country Link
US (2) US8791273B2 (ru)
EP (1) EP2496555B1 (ru)
JP (1) JP2013510081A (ru)
CN (1) CN102596905B (ru)
AR (1) AR078904A1 (ru)
CA (1) CA2780040C (ru)
CY (1) CY1114881T1 (ru)
DK (1) DK2496555T3 (ru)
EA (1) EA019890B1 (ru)
ES (1) ES2434024T3 (ru)
HR (1) HRP20131086T1 (ru)
LV (1) LV14346B (ru)
PL (1) PL2496555T3 (ru)
PT (1) PT2496555E (ru)
RS (1) RS53014B (ru)
SI (1) SI2496555T1 (ru)
UA (1) UA107367C2 (ru)
WO (1) WO2011054888A1 (ru)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3127539A1 (en) * 2015-08-03 2017-02-08 Latvian Institute Of Organic Synthesis Use of 2-(5s-methyl-2-oxo-4r-phenyl-pyrrolidin-1-yl)-acetamide in the treatment of seizures
RU2711655C1 (ru) * 2019-09-13 2020-01-20 Федеральное государственное бюджетное образовательное учреждение высшего образования "Российский национальный исследовательский медицинский университет имени Н.И. Пирогова" Министерства здравоохранения Российской Федерации Способ крупномасштабного синтеза калиевой соли 2-[2-(2-оксо-4-фенилпирролидин-1-ил)ацетамидо]этансульфокислоты

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2186236B1 (ru) * 1972-05-03 1975-08-01 Logeais Labor Jacques
CN1040747C (zh) * 1994-05-07 1998-11-18 中国科学院昆明植物研究所 N－取代基－4－取代苯基－5－烷基－5－取代苄基吡咯烷酮－2,其中间体,其合成方其法及应用
MXPA03005889A (es) * 2000-12-28 2005-02-14 Daiichi Seiyaku Co Agente para tratamiento terapeutico y profilactico del dolor neuropatico.
ATE459350T1 (de) * 2003-12-24 2010-03-15 Hideki Ohyama Behandlung von schwerer aphasie bei chronischen zerebrovaskulären erkrankungen
GB0412019D0 (en) * 2004-05-28 2004-06-30 Novartis Ag Organic compounds
LV13630B (en) * 2006-03-16 2007-12-20 Olainfarm As Method of preparation and use of pharmaceutically active n-carbamoylmethyl-4(r)-phenyl-2-pyrrolidinone

Also Published As

Publication number Publication date
LV14346B (lv) 2011-07-20
SI2496555T1 (sl) 2013-12-31
US20140296317A1 (en) 2014-10-02
PT2496555E (pt) 2013-12-02
HRP20131086T1 (hr) 2013-12-20
CA2780040A1 (en) 2011-05-12
RS53014B (sr) 2014-04-30
JP2013510081A (ja) 2013-03-21
CY1114881T1 (el) 2016-12-14
CA2780040C (en) 2014-04-08
US20120215010A1 (en) 2012-08-23
CN102596905A (zh) 2012-07-18
US8791273B2 (en) 2014-07-29
WO2011054888A1 (en) 2011-05-12
EP2496555A1 (en) 2012-09-12
LV14346A (lv) 2011-05-20
UA107367C2 (xx) 2014-12-25
CN102596905B (zh) 2014-07-16
PL2496555T3 (pl) 2014-01-31
EP2496555B1 (en) 2013-08-28
ES2434024T3 (es) 2013-12-13
EA019890B1 (ru) 2014-07-30
AR078904A1 (es) 2011-12-14
DK2496555T3 (da) 2013-11-11

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