WO2015092638A1 - Formes polymorphes de n-carbamoylméthyl-4(r)-phényl-2-pyrrolidone - Google Patents

Formes polymorphes de n-carbamoylméthyl-4(r)-phényl-2-pyrrolidone Download PDF

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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
Application number
PCT/IB2014/066849
Other languages
English (en)
Inventor
Vilnis LIEPINS
Galina KUHAREVA
Mihails KOVALSKIS
Raimonds TERENTJEVS
Original Assignee
Jsc Olainfarm
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 Jsc Olainfarm filed Critical Jsc Olainfarm
Priority to EA201691191A priority Critical patent/EA029298B1/ru
Publication of WO2015092638A1 publication Critical patent/WO2015092638A1/fr

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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)

Abstract

Cette invention concerne des formes polymorphes cristallines de N-carbamoylméthyl-4(R)-phényl-2-pyrrolidone et leurs procédés de production, ainsi que l'utilisation de ces formes polymorphes pour la production de compositions pharmaceutiques.
PCT/IB2014/066849 2013-12-18 2014-12-12 Formes polymorphes de n-carbamoylméthyl-4(r)-phényl-2-pyrrolidone WO2015092638A1 (fr)

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-13-215A LV15016B (lv) 2013-12-18 2013-12-18 N-karbamoilmetil-4(R)-fenil-2-pirolidinona polimorfās formas
LVP-13-215 2013-12-18

Publications (1)

Publication Number Publication Date
WO2015092638A1 true WO2015092638A1 (fr) 2015-06-25

Family

ID=52462347

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2014/066849 WO2015092638A1 (fr) 2013-12-18 2014-12-12 Formes polymorphes de n-carbamoylméthyl-4(r)-phényl-2-pyrrolidone

Country Status (3)

Country Link
EA (1) EA029298B1 (fr)
LV (1) LV15016B (fr)
WO (1) WO2015092638A1 (fr)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007104780A2 (fr) 2006-03-16 2007-09-20 Akciju Sabiedriba 'olainfarm' Procédé de préparation et d'utilisation de n-carbamoylmethyl-4(r)-phenyl-2-pyrrolidinone pharmacologiquement actif

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007104780A2 (fr) 2006-03-16 2007-09-20 Akciju Sabiedriba 'olainfarm' Procédé de préparation et d'utilisation de n-carbamoylmethyl-4(r)-phenyl-2-pyrrolidinone pharmacologiquement actif
EP2013166A2 (fr) 2006-03-16 2009-01-14 Akciju Sabiedriba "Olainfarm" N-carbamoylmethyl-4(r)phenyl-2-pyrrolidinone, procedes de preparation et utilisation pharmaceutique
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)

* Cited by examiner, † Cited by third party
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
EA029298B1 (ru) 2018-03-30
LV15016B (lv) 2016-01-20
EA201691191A1 (ru) 2016-12-30
LV15016A (lv) 2015-06-20

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