LV14346A - 2-(4-Fenil-5-metil-2-oksopirolidin-1-il)-acetamīda 4R,5S-enantiomērs ar nootropo aktivitāti - Google Patents
2-(4-Fenil-5-metil-2-oksopirolidin-1-il)-acetamīda 4R,5S-enantiomērs ar nootropo aktivitātiInfo
- Publication number
- LV14346A LV14346A LVP-09-193A LV090193A LV14346A LV 14346 A LV14346 A LV 14346A LV 090193 A LV090193 A LV 090193A LV 14346 A LV14346 A LV 14346A
- Authority
- LV
- Latvia
- Prior art keywords
- pyrrolidin
- oxo
- phenyl
- enantiomer
- acetamide
- Prior art date
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)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (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
Izgudrojums attiecas uz 2-(4-fenil-5-metil-2-okso-pirolidin-1-il)-acetamīda 4R,5S-enantiomēru, kam ir atmiņu uzlabojošas īpašības, un šī savienojuma iegūšanas metodi, kas sastāv no 5S-metil-4R-fenilpirolidin-2-ona sintēzes, tā N-alkilēšanas ar halogēnetiķskābes esteri, un izveidojušās starpprodukta 2-(4-fenil-5-metil-2-okso-pirolidin-1-il)-etiķskābes etilestera apstrādes ar amonjaku.
Priority Applications (19)
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 |
UAA201206776A UA107367C2 (xx) | 2009-11-05 | 2010-04-11 | 4r,5s-енантіомер 2-(5-метил-2-оксо-4-фенілпіролідин-1-іл)ацетамід з ноотропною активністю |
ARP100104073A AR078904A1 (es) | 2009-11-05 | 2010-11-04 | Enantiomero 4r,5s de 2-(5-metil-2-oxo-4-fenil-pirrolidin-1-il)-acetamida con actividad nootropica |
US13/508,184 US8791273B2 (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 |
CN201080050216.9A CN102596905B (zh) | 2009-11-05 | 2010-11-04 | 具有促智活性的2-(5-甲基-2-氧代-4-苯基-吡咯烷-1-基)-乙酰胺的4r, 5s -对映异构体 |
ES10776339T ES2434024T3 (es) | 2009-11-05 | 2010-11-04 | Enantiómero 4R,5S de 2-(5-metil-2-oxo-4-fenil-pirrolidin-1-il)-acetamida con actividad nootrópica |
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 |
SI201030416T SI2496555T1 (sl) | 2009-11-05 | 2010-11-04 | 4r,5s-enantiomer 2-(5-metil-2-okso-4-fenil-pirolidin-1-il)-acetamida z nootropiäśno aktivnostjo |
PL10776339T PL2496555T3 (pl) | 2009-11-05 | 2010-11-04 | Enancjomer 4R,5S 2-(5-metylo-2-okso-4-fenylo-pirolidyn-1-ylo)acetamidu o aktywności nootropowej |
DK10776339.3T DK2496555T3 (da) | 2009-11-05 | 2010-11-04 | 4r,5s-enantiomer af 2-(5-methyl-2-oxo-4-phenyl-pyrrolidin-1-yl)-acetamid med nootropisk aktivitet |
JP2012535876A JP2013510081A (ja) | 2009-11-05 | 2010-11-04 | 向知性作用を有する2−(5−メチル−2−オキソ−4−フェニル−ピロリジン−1−イル)−アセトアミドの4r,5s−エナンチオマー |
EP10776339.3A EP2496555B1 (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 |
CA2780040A CA2780040C (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 |
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 |
RS20130474A RS53014B (en) | 2009-11-05 | 2010-11-04 | 4R, 5S-ENANTIOMER 2- (5-METHYL-2-OXO-4-PHENYL-PYROLIDIN-1-IL) -ACETAMIDE WITH NOOTROPIC ACTIVITY |
PT107763393T PT2496555E (pt) | 2009-11-05 | 2010-11-04 | Enantiómero 4r,5s de -2-(5-metil-2-oxo-4-fenil-pirrolidin- 1-il)-acetamida com actividade nootrópica |
HRP20131086AT HRP20131086T1 (hr) | 2009-11-05 | 2013-11-13 | 4r,5s-enantiomer 2-(5-metil-2-okso-4-fenil-pirolidin-1-il)-acetamida s nootropskim djelovanjem |
CY20131101066T CY1114881T1 (el) | 2009-11-05 | 2013-11-27 | 4r, 5s-εναντιομερες του 2-(5-μεθυλ-2-οξο-4-φαινυλ-πυρρολιδιν-1-υλ)-ακεταμιδιου με νοοτροπο δραστικοτητα |
US14/305,382 US20140296317A1 (en) | 2009-11-05 | 2014-06-16 | 4r,5s-enantiomer of 2-(5-methyl-2-oxo-4-phenyl-pyrrolidin-1-yl)-acetamide with nootropic activity |
Applications Claiming Priority (1)
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 |
Publications (2)
Publication Number | Publication Date |
---|---|
LV14346A true LV14346A (lv) | 2011-05-20 |
LV14346B LV14346B (lv) | 2011-07-20 |
Family
ID=43466928
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
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 |
Country Status (18)
Country | Link |
---|---|
US (2) | US8791273B2 (lv) |
EP (1) | EP2496555B1 (lv) |
JP (1) | JP2013510081A (lv) |
CN (1) | CN102596905B (lv) |
AR (1) | AR078904A1 (lv) |
CA (1) | CA2780040C (lv) |
CY (1) | CY1114881T1 (lv) |
DK (1) | DK2496555T3 (lv) |
EA (1) | EA019890B1 (lv) |
ES (1) | ES2434024T3 (lv) |
HR (1) | HRP20131086T1 (lv) |
LV (1) | LV14346B (lv) |
PL (1) | PL2496555T3 (lv) |
PT (1) | PT2496555E (lv) |
RS (1) | RS53014B (lv) |
SI (1) | SI2496555T1 (lv) |
UA (1) | UA107367C2 (lv) |
WO (1) | WO2011054888A1 (lv) |
Families Citing this family (2)
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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2186236B1 (lv) * | 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 |
JPWO2002053153A1 (ja) * | 2000-12-28 | 2004-04-30 | 第一製薬株式会社 | 神経因性疼痛治療及び予防薬 |
JPWO2005061454A1 (ja) * | 2003-12-24 | 2007-07-12 | 秀樹 大山 | 脳血管障害慢性期の重度失語症に対する治療剤又は治療方法 |
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 |
-
2009
- 2009-11-05 LV LVP-09-193A patent/LV14346B/lv unknown
-
2010
- 2010-04-11 UA UAA201206776A patent/UA107367C2/ru unknown
- 2010-11-04 PT PT107763393T patent/PT2496555E/pt unknown
- 2010-11-04 US US13/508,184 patent/US8791273B2/en not_active Expired - Fee Related
- 2010-11-04 DK DK10776339.3T patent/DK2496555T3/da active
- 2010-11-04 JP JP2012535876A patent/JP2013510081A/ja active Pending
- 2010-11-04 WO PCT/EP2010/066767 patent/WO2011054888A1/en active Application Filing
- 2010-11-04 SI SI201030416T patent/SI2496555T1/sl unknown
- 2010-11-04 CN CN201080050216.9A patent/CN102596905B/zh not_active Expired - Fee Related
- 2010-11-04 AR ARP100104073A patent/AR078904A1/es not_active Application Discontinuation
- 2010-11-04 PL PL10776339T patent/PL2496555T3/pl unknown
- 2010-11-04 RS RS20130474A patent/RS53014B/en unknown
- 2010-11-04 EP EP10776339.3A patent/EP2496555B1/en active Active
- 2010-11-04 EA EA201200536A patent/EA019890B1/ru unknown
- 2010-11-04 CA CA2780040A patent/CA2780040C/en not_active Expired - Fee Related
- 2010-11-04 ES ES10776339T patent/ES2434024T3/es active Active
-
2013
- 2013-11-13 HR HRP20131086AT patent/HRP20131086T1/hr unknown
- 2013-11-27 CY CY20131101066T patent/CY1114881T1/el unknown
-
2014
- 2014-06-16 US US14/305,382 patent/US20140296317A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
US8791273B2 (en) | 2014-07-29 |
LV14346B (lv) | 2011-07-20 |
CY1114881T1 (el) | 2016-12-14 |
CN102596905B (zh) | 2014-07-16 |
CA2780040C (en) | 2014-04-08 |
US20140296317A1 (en) | 2014-10-02 |
DK2496555T3 (da) | 2013-11-11 |
SI2496555T1 (sl) | 2013-12-31 |
HRP20131086T1 (hr) | 2013-12-20 |
PT2496555E (pt) | 2013-12-02 |
CA2780040A1 (en) | 2011-05-12 |
EP2496555A1 (en) | 2012-09-12 |
US20120215010A1 (en) | 2012-08-23 |
CN102596905A (zh) | 2012-07-18 |
UA107367C2 (xx) | 2014-12-25 |
PL2496555T3 (pl) | 2014-01-31 |
ES2434024T3 (es) | 2013-12-13 |
EA019890B1 (ru) | 2014-07-30 |
JP2013510081A (ja) | 2013-03-21 |
WO2011054888A1 (en) | 2011-05-12 |
RS53014B (en) | 2014-04-30 |
AR078904A1 (es) | 2011-12-14 |
EA201200536A1 (ru) | 2012-09-28 |
EP2496555B1 (en) | 2013-08-28 |
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