WO2007104780A2 - N- carbamoylmethyl- 4- (r) -phenyl-2-pyrr0lidin0ne, method of its preparation and pharmaceutical use - Google Patents
N- carbamoylmethyl- 4- (r) -phenyl-2-pyrr0lidin0ne, method of its preparation and pharmaceutical use Download PDFInfo
- Publication number
- WO2007104780A2 WO2007104780A2 PCT/EP2007/052424 EP2007052424W WO2007104780A2 WO 2007104780 A2 WO2007104780 A2 WO 2007104780A2 EP 2007052424 W EP2007052424 W EP 2007052424W WO 2007104780 A2 WO2007104780 A2 WO 2007104780A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- phenyl
- pyrrolidinone
- carphedon
- carbamoylmethyl
- compound
- 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
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- 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
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Definitions
- the invention relates to the discovery of the biologically active i?-enantiomer of N- carbamoylmethyl-4-aryl-2-pyrrolidinone and easy and effective method of its preparation.
- N- carbamoylmethyl-4-aryl-2-pyrrolidinone (Carphedon, INN) could be regarded as a much more perspective psycho-stimulator due to the less pronounced side effects.
- the invention relates to the i?-enantiomer of 4-phenyl-l-pyrrolidineacetic acid amide. More particularly, the invention relates to N-carbamoylmethyl-4(i?)-phenyl-2-pyrrolidinone of the formula:
- i?-Carphedon 4 the same as S-Carphedon 4a can be easily achieved by the means of the N-alkylation of available 4(i?)-phenyl-2- pyrrolidinone (1) or 4(5)-phenyl-2-pyrrolidinone (Ia) with ethyl bromoacetate (2) in the presence of a strong base and by the following transformation of ethoxycarbonyl group in the intermediate 2-pyrrolidinones 3 and 3a into carbamoyl function by the treatment with ammonia.
- Example 1 N-Carbamoylmethyl-4(R)-phenyl-2-pyrrolidinone (4).
- the solution of 4(i?)-phenyl-2- pyrrolidinone (1) (345 mg, 2.14 mM) in 1,4-dioxane (30 ml) was added to the suspension of sodium hydride (56 mg, 2.35 mM) in 1,4-dioxane (30 ml).
- the mixture was heated at 80 ⁇ 90°C during 30 min and then cooled to room temperature.
- Ethyl bromoacetate (393 mg, 2.37 mM) was added and the reaction mixture was refluxed at 110 ⁇ 120°C for 6 hours. Obtained mixture was concentrated under reduced pressure.
Abstract
Description
Claims
Priority Applications (13)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DK07726915.7T DK2013166T3 (en) | 2006-03-16 | 2007-03-15 | N-carbamoylmethyl-4 (R) -phenyl-2-pyrrolidone, process for its preparation and pharmaceutical use |
SI200730253T SI2013166T1 (en) | 2006-03-16 | 2007-03-15 | N-carbamoylmethyl-4(r)-phenyl-2-pyrrolidinone, method of its preparation and pharmaceutical use |
EA200801978A EA014668B1 (en) | 2006-03-16 | 2007-03-15 | Method for manufacturing and use of pharmacologically active n-carbamoylmethyl-4(r)-phenyl-2-pyrrolidone |
MEP-2009-293A ME01192B (en) | 2006-03-16 | 2007-03-15 | N- carbamoylmethyl- 4- (r) -phenyl-2-pyrr0lidin0ne, method of its preparation and pharmaceutical use |
CA2647206A CA2647206C (en) | 2006-03-16 | 2007-03-15 | N-carbamoylmethyl-4-(r)-phenyl-2-pyrrolidinone, method of its preparation and pharmaceutical use |
EEP200800063A EE05536B1 (en) | 2006-03-16 | 2007-03-15 | N-Carbamoylmethyl-4- (R) -phenyl-2-pyrrolidinone, process for its preparation and pharmaceutical use |
PL07726915T PL2013166T3 (en) | 2006-03-16 | 2007-03-15 | N-carbamoylmethyl-4(r)-phenyl-2-pyrrolidinone, method of its preparation and pharmaceutical use |
EP07726915A EP2013166B1 (en) | 2006-03-16 | 2007-03-15 | N-carbamoylmethyl-4(r)-phenyl-2-pyrrolidinone, method of its preparation and pharmaceutical use |
AT07726915T ATE460396T1 (en) | 2006-03-16 | 2007-03-15 | N-CARBAMOYLMETHYL-4-(R)-PHENYL-2-PYRROLIDINONE, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL USE |
US12/226,332 US9102615B2 (en) | 2006-03-16 | 2007-03-15 | N-Carbamoylmethy1-4-(R)-phenyl-2-pyrrolidinone, method of its preparation and pharmaceutical use |
DE602007005244T DE602007005244D1 (en) | 2006-03-16 | 2007-03-15 | N-CARBAMOYLMETHYL-4- (R) -PHENYL-2-PYRROLIDINONE, METHOD FOR ITS PREPARATION AND PHARMACEUTICAL USE |
HRP20090524AA HRP20090524C1 (en) | 2006-03-16 | 2009-09-30 | Method of preparation and use pharmacologically active n-carbamoylmethyl-4(r)-phenyl-2-pyrrolidinone |
US14/688,633 US9382203B2 (en) | 2006-03-16 | 2015-04-16 | N-carbamoylmethyl-4-(R)-phenyl-2-pyrrolidinone, method of its preparation and pharmaceutical use |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
LVP-06-45A LV13630B (en) | 2006-03-16 | 2006-03-16 | Method of preparation and use of pharmaceutically active n-carbamoylmethyl-4(r)-phenyl-2-pyrrolidinone |
LVP-06-45 | 2006-03-16 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/226,332 A-371-Of-International US9102615B2 (en) | 2006-03-16 | 2007-03-15 | N-Carbamoylmethy1-4-(R)-phenyl-2-pyrrolidinone, method of its preparation and pharmaceutical use |
US14/688,633 Division US9382203B2 (en) | 2006-03-16 | 2015-04-16 | N-carbamoylmethyl-4-(R)-phenyl-2-pyrrolidinone, method of its preparation and pharmaceutical use |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2007104780A2 true WO2007104780A2 (en) | 2007-09-20 |
WO2007104780A3 WO2007104780A3 (en) | 2007-11-29 |
Family
ID=38461010
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2007/052424 WO2007104780A2 (en) | 2006-03-16 | 2007-03-15 | N- carbamoylmethyl- 4- (r) -phenyl-2-pyrr0lidin0ne, method of its preparation and pharmaceutical use |
Country Status (21)
Country | Link |
---|---|
US (2) | US9102615B2 (en) |
EP (1) | EP2013166B1 (en) |
CN (1) | CN101448786A (en) |
AT (1) | ATE460396T1 (en) |
CA (1) | CA2647206C (en) |
CY (1) | CY1110170T1 (en) |
DE (1) | DE602007005244D1 (en) |
DK (1) | DK2013166T3 (en) |
EA (1) | EA014668B1 (en) |
EE (1) | EE05536B1 (en) |
ES (1) | ES2342024T3 (en) |
GE (1) | GEP20104915B (en) |
HR (1) | HRP20090524C1 (en) |
LT (1) | LT5589B (en) |
LV (1) | LV13630B (en) |
ME (1) | ME01192B (en) |
PL (1) | PL2013166T3 (en) |
PT (1) | PT2013166E (en) |
SI (1) | SI2013166T1 (en) |
UA (1) | UA96440C2 (en) |
WO (1) | WO2007104780A2 (en) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011054888A1 (en) * | 2009-11-05 | 2011-05-12 | Grindeks, A Joint Stock Company | 4r,5s-enantiomer of 2-(5-methyl-2-oxo-4-phenyl-pyrrolidin-1-yl)-acetamide with nootropic activity |
WO2012123358A1 (en) * | 2011-03-11 | 2012-09-20 | Grindeks | 4r,5r-enantiomer of 2-(5-methyl-2-oxo-4-phenyl-pyrrolidin-1-yl)-acetamide with nootropic activity |
WO2013043085A1 (en) | 2011-09-22 | 2013-03-28 | Akhapkina Valentina Ivanovna | Pharmaceutical substance (variants) and compositions based thereon which exhibit modulatory activity with a commensurate effect |
WO2014005721A1 (en) | 2012-07-05 | 2014-01-09 | Merz Pharma Gmbh & Co. Kgaa | Use of (r)-phenylpiracetam for the treatment of parkinson's disease |
WO2014005720A1 (en) | 2012-07-05 | 2014-01-09 | Merz Pharma Gmbh & Co. Kgaa | Use of (r)-phenylpiracetam for the treatment of disease-associated fatigue |
WO2015060702A1 (en) * | 2013-10-22 | 2015-04-30 | Latvian Institute Of Organic Synthesis | Pharmaceutical composition for controlling body mass gain comprising s-phenotropil |
WO2015087291A1 (en) | 2013-12-13 | 2015-06-18 | Jsc Olainfarm | 3-carboxy-4-(r)-phenylpyrrolydine-2-one salt and its use |
WO2015092638A1 (en) | 2013-12-18 | 2015-06-25 | Jsc Olainfarm | N-carbamoylmethyl-4(r)-phenyl-2-pyrrolidone polymorphic forms |
EP2891491A1 (en) | 2014-01-03 | 2015-07-08 | Merz Pharma GmbH & Co. KGaA | Use of (r)-phenylpiracetam for the treatment of sleep disorders |
WO2015173763A1 (en) | 2014-05-14 | 2015-11-19 | Akciju Sabiedriba "Olainfarm" | Pharmaceutical composition for the prevention and treatment of diseases associated with elevated inducible nitric oxide synthase |
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 |
Families Citing this family (1)
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---|---|---|---|---|
HUE050993T2 (en) | 2012-05-08 | 2021-01-28 | Nicox Ophthalmics Inc | Polymorphic form of fluticasone propionate |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1619182A1 (en) | 2003-04-10 | 2006-01-25 | Akhapkina, Valentina Ivanova | Substance exhibiting antidepressant property |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB0004297D0 (en) * | 2000-02-23 | 2000-04-12 | Ucb Sa | 2-oxo-1 pyrrolidine derivatives process for preparing them and their uses |
RU2289404C1 (en) * | 2005-04-06 | 2006-12-20 | ГОУ ВПО "Московский государственный медико-стоматологический университет Министерства здравоохранения РФ" | Method for premedication in patients with mean level of psychoemotional stress in ambulatory stomatological surgery |
-
2006
- 2006-03-16 LV LVP-06-45A patent/LV13630B/en unknown
-
2007
- 2007-03-15 PT PT07726915T patent/PT2013166E/en unknown
- 2007-03-15 UA UAA200812099A patent/UA96440C2/en unknown
- 2007-03-15 ME MEP-2009-293A patent/ME01192B/en unknown
- 2007-03-15 EA EA200801978A patent/EA014668B1/en not_active IP Right Cessation
- 2007-03-15 US US12/226,332 patent/US9102615B2/en not_active Expired - Fee Related
- 2007-03-15 DE DE602007005244T patent/DE602007005244D1/en active Active
- 2007-03-15 AT AT07726915T patent/ATE460396T1/en active
- 2007-03-15 CA CA2647206A patent/CA2647206C/en not_active Expired - Fee Related
- 2007-03-15 ES ES07726915T patent/ES2342024T3/en active Active
- 2007-03-15 WO PCT/EP2007/052424 patent/WO2007104780A2/en active Application Filing
- 2007-03-15 SI SI200730253T patent/SI2013166T1/en unknown
- 2007-03-15 GE GEAP200710934A patent/GEP20104915B/en unknown
- 2007-03-15 DK DK07726915.7T patent/DK2013166T3/en active
- 2007-03-15 CN CNA2007800177832A patent/CN101448786A/en active Pending
- 2007-03-15 PL PL07726915T patent/PL2013166T3/en unknown
- 2007-03-15 EE EEP200800063A patent/EE05536B1/en not_active IP Right Cessation
- 2007-03-15 EP EP07726915A patent/EP2013166B1/en active Active
-
2008
- 2008-09-22 LT LT2008075A patent/LT5589B/en not_active IP Right Cessation
-
2009
- 2009-09-30 HR HRP20090524AA patent/HRP20090524C1/en not_active IP Right Cessation
-
2010
- 2010-06-08 CY CY20101100506T patent/CY1110170T1/en unknown
-
2015
- 2015-04-16 US US14/688,633 patent/US9382203B2/en active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1619182A1 (en) | 2003-04-10 | 2006-01-25 | Akhapkina, Valentina Ivanova | Substance exhibiting antidepressant property |
Cited By (20)
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JP2013510081A (en) * | 2009-11-05 | 2013-03-21 | グリンデクス,ア ジョイント ストック カンパニー | 4R, 5S-enantiomer of 2- (5-methyl-2-oxo-4-phenyl-pyrrolidin-1-yl) -acetamide with nootropic effect |
US8791273B2 (en) | 2009-11-05 | 2014-07-29 | Jsc Grindeks | 4R,5S-enantiomer of 2-(5-methyl-2-oxo-4-phenyl-pyrrolidin-1-yl)-acetamide with nootropic activity |
EA019890B1 (en) * | 2009-11-05 | 2014-07-30 | Гриндекс, Джоинт Сток Кампани | 4r,5s-enantiomer of 2-(5-methyl-2-oxo-4-phenylpyrrolidin-1-yl)acetamide with nootropic activity |
WO2011054888A1 (en) * | 2009-11-05 | 2011-05-12 | Grindeks, A Joint Stock Company | 4r,5s-enantiomer of 2-(5-methyl-2-oxo-4-phenyl-pyrrolidin-1-yl)-acetamide with nootropic activity |
WO2012123358A1 (en) * | 2011-03-11 | 2012-09-20 | Grindeks | 4r,5r-enantiomer of 2-(5-methyl-2-oxo-4-phenyl-pyrrolidin-1-yl)-acetamide with nootropic activity |
EP2762138A4 (en) * | 2011-09-22 | 2015-12-02 | Valentina Ivanovna Akhapkina | Pharmaceutical substance (variants) and compositions based thereon which exhibit modulatory activity with a commensurate effect |
WO2013043085A1 (en) | 2011-09-22 | 2013-03-28 | Akhapkina Valentina Ivanovna | Pharmaceutical substance (variants) and compositions based thereon which exhibit modulatory activity with a commensurate effect |
MD20140042A2 (en) * | 2011-09-22 | 2014-09-30 | Akhapkina Valentina Ivanovna | (RS)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide compound which exhibits modulatory activity with a commensurable effect, pharmaceutical substance (variants) and use thereof, composition (variants) |
WO2014005721A1 (en) | 2012-07-05 | 2014-01-09 | Merz Pharma Gmbh & Co. Kgaa | Use of (r)-phenylpiracetam for the treatment of parkinson's disease |
WO2014005720A1 (en) | 2012-07-05 | 2014-01-09 | Merz Pharma Gmbh & Co. Kgaa | Use of (r)-phenylpiracetam for the treatment of disease-associated fatigue |
WO2015060702A1 (en) * | 2013-10-22 | 2015-04-30 | Latvian Institute Of Organic Synthesis | Pharmaceutical composition for controlling body mass gain comprising s-phenotropil |
WO2015087291A1 (en) | 2013-12-13 | 2015-06-18 | Jsc Olainfarm | 3-carboxy-4-(r)-phenylpyrrolydine-2-one salt and its use |
WO2015092638A1 (en) | 2013-12-18 | 2015-06-25 | Jsc Olainfarm | N-carbamoylmethyl-4(r)-phenyl-2-pyrrolidone polymorphic forms |
EA029298B1 (en) * | 2013-12-18 | 2018-03-30 | Акционерное Общество "Олайнфарм" | N-carbamoylmethyl-4(r)-phenyl-2-pyrrolidone polymorphic forms |
EP2891491A1 (en) | 2014-01-03 | 2015-07-08 | Merz Pharma GmbH & Co. KGaA | Use of (r)-phenylpiracetam for the treatment of sleep disorders |
WO2015173763A1 (en) | 2014-05-14 | 2015-11-19 | Akciju Sabiedriba "Olainfarm" | Pharmaceutical composition for the prevention and treatment of diseases associated with elevated inducible nitric oxide synthase |
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 |
WO2017021881A1 (en) * | 2015-08-03 | 2017-02-09 | Latvian Institute Of Organic Synthesis | Use of 2-(5s-methyl-2-oxo-4r-phenyl-pyrrolidin-1-yl)-acetamide in the treatment of seizures |
US10105348B2 (en) | 2015-08-03 | 2018-10-23 | Latvian Institute Of Organic Synthesis | Use of 2-(5S-methyl-2-oxo-4R-phenyl-pyrrolidin-1-yl)-acetamide in the treatment of seizures |
EA036085B1 (en) * | 2015-08-03 | 2020-09-24 | Латвийский Институт Органического Синтеза | Use of 2-(5s-methyl-2-oxo-4r-phenyl-pyrrolidin-1-yl)acetamide in the treatment of seizures |
Also Published As
Publication number | Publication date |
---|---|
US9102615B2 (en) | 2015-08-11 |
UA96440C2 (en) | 2011-11-10 |
PT2013166E (en) | 2010-06-09 |
EP2013166A2 (en) | 2009-01-14 |
CA2647206A1 (en) | 2007-09-20 |
DK2013166T3 (en) | 2010-07-05 |
LT2008075A (en) | 2009-06-25 |
GEP20104915B (en) | 2010-03-10 |
ES2342024T3 (en) | 2010-06-30 |
WO2007104780A3 (en) | 2007-11-29 |
EP2013166B1 (en) | 2010-03-10 |
DE602007005244D1 (en) | 2010-04-22 |
EA200801978A1 (en) | 2009-04-28 |
LT5589B (en) | 2009-08-25 |
HRP20090524C1 (en) | 2017-03-10 |
US9382203B2 (en) | 2016-07-05 |
CN101448786A (en) | 2009-06-03 |
HRPK20090524B3 (en) | 2012-12-31 |
EE200800063A (en) | 2008-12-15 |
PL2013166T3 (en) | 2010-08-31 |
ME01192B (en) | 2012-12-20 |
HRP20090524A2 (en) | 2009-12-31 |
CA2647206C (en) | 2011-09-27 |
SI2013166T1 (en) | 2010-07-30 |
EA014668B1 (en) | 2010-12-30 |
ATE460396T1 (en) | 2010-03-15 |
US20100022784A1 (en) | 2010-01-28 |
US20150216846A1 (en) | 2015-08-06 |
LV13630B (en) | 2007-12-20 |
EE05536B1 (en) | 2012-04-16 |
CY1110170T1 (en) | 2015-01-14 |
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