WO2015092638A1 - N-carbamoylmethyl-4(r)-phenyl-2-pyrrolidone polymorphic forms - Google Patents
N-carbamoylmethyl-4(r)-phenyl-2-pyrrolidone polymorphic forms Download PDFInfo
- Publication number
- WO2015092638A1 WO2015092638A1 PCT/IB2014/066849 IB2014066849W WO2015092638A1 WO 2015092638 A1 WO2015092638 A1 WO 2015092638A1 IB 2014066849 W IB2014066849 W IB 2014066849W WO 2015092638 A1 WO2015092638 A1 WO 2015092638A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- carbamoylmethyl
- pyrrolidone
- phenyl
- crystalline form
- polymorph
- 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
Definitions
- Dissolution rate of the Polymorph II is better than that of Polymorph I. This property may positively influence bioavailability of the active ingredient of the dosage form upon dissolution in organism.
- Polymorphs obtained by methods according to this invention are suitable for preparation of pharmaceutical compositions.
- Pharmaceutical composition, comprising N- carbamoylmethyl-4(i?)-phenyl-2-pyrrolidone polymorph and at least one pharmaceutically acceptable excipient is suitable for use as psychometabolic stimulator.
- N-carbamoylmethyl-4(i?)-phenyl-2-pyrrolidone (40 g) was dissolved in isopanol (140 ml) at reflux temperature. Then the solution was slowly cooled down to 50-55 °C and N- carbamoylmethyl-4(i?)-phenyl-2-pyrrolidone polymorph II crystal seeds (0.5 g) were added. The obtained suspension was slowly cooled down to 45-49 °C and kept at this temperature for 30 min. Then the suspension was slowly cooled down to 1 -5 °C and kept at this temperature for 5 h. Then the precipitated crystals were filtered off and washed on filter with isopropanol (40 ml) and then dried at 45-50 °C for 8 h. Yield 35.9-37.5 g (90-94%).
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EA201691191A EA029298B1 (ru) | 2013-12-18 | 2014-12-12 | Полиморфные формы n-карбамоилметил-4(r)-фенил-2-пирролидона |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
LVP-13-215 | 2013-12-18 | ||
LVP-13-215A LV15016B (lv) | 2013-12-18 | 2013-12-18 | N-karbamoilmetil-4(R)-fenil-2-pirolidinona polimorfās formas |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2015092638A1 true WO2015092638A1 (en) | 2015-06-25 |
Family
ID=52462347
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/IB2014/066849 WO2015092638A1 (en) | 2013-12-18 | 2014-12-12 | N-carbamoylmethyl-4(r)-phenyl-2-pyrrolidone polymorphic forms |
Country Status (3)
Country | Link |
---|---|
EA (1) | EA029298B1 (ru) |
LV (1) | LV15016B (ru) |
WO (1) | WO2015092638A1 (ru) |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007104780A2 (en) | 2006-03-16 | 2007-09-20 | Akciju Sabiedriba 'olainfarm' | N- carbamoylmethyl- 4- (r) -phenyl-2-pyrr0lidin0ne, method of its preparation and pharmaceutical use |
-
2013
- 2013-12-18 LV LVP-13-215A patent/LV15016B/lv unknown
-
2014
- 2014-12-12 WO PCT/IB2014/066849 patent/WO2015092638A1/en active Application Filing
- 2014-12-12 EA EA201691191A patent/EA029298B1/ru unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007104780A2 (en) | 2006-03-16 | 2007-09-20 | Akciju Sabiedriba 'olainfarm' | N- carbamoylmethyl- 4- (r) -phenyl-2-pyrr0lidin0ne, method of its preparation and pharmaceutical use |
EP2013166A2 (en) | 2006-03-16 | 2009-01-14 | Akciju Sabiedriba "Olainfarm" | N-carbamoylmethyl-4(r)-phenyl-2-pyrrolidinone, method of its preparation and pharmaceutical use |
US20100022784A1 (en) | 2006-03-16 | 2010-01-28 | Joint Stock Company "Olainfarm" | N-Carbamoylmethyl-4-(R)-Phenyl-2-Pyrrolidinone, Method of its Preparation and Pharmaceutical Use |
Non-Patent Citations (4)
Title |
---|
"CRYSTALLINE FORM OF N-(CARBAMOYLMETHYL-4-PHENYL-2-PYRROLIDINONE AND INTERMEDIATES THEREOF", IP.COM JOURNAL, IP.COM INC., WEST HENRIETTA, NY, US, 17 November 2011 (2011-11-17), XP013148057, ISSN: 1533-0001 * |
J. MED. CHEM, 1984 |
M VORONA ET AL: "NOVEL METHODS FOR THE SYNTHESIS OF 2-[(4R)-2-OXO-4-PHENYLPYRROLIDIN-1-YL]- ACETAMIDE ((R)-PHENOTROPIL)", CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 1 January 2012 (2012-01-01), pages 720 - 723, XP055177579, Retrieved from the Internet <URL:http://rd.springer.com/content/pdf/10.1007/s10593-012-1050-y.pdf> [retrieved on 20150318] * |
PHARM. CHEM. JOURNAL, vol. 14, no. 11, 1980, pages 776 |
Also Published As
Publication number | Publication date |
---|---|
LV15016B (lv) | 2016-01-20 |
EA029298B1 (ru) | 2018-03-30 |
EA201691191A1 (ru) | 2016-12-30 |
LV15016A (lv) | 2015-06-20 |
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