EP 3286168 A1 20180228 - A SOLID FORM OF APREMILAST AND A PROCESS FOR PREPARING THE SAME
Title (en)
A SOLID FORM OF APREMILAST AND A PROCESS FOR PREPARING THE SAME
Title (de)
FESTE FORM VON APREMILAST UND VERFAHREN ZU IHRER HERSTELLUNG
Title (fr)
FORME SOLIDE D'APRÉMILAST ET UN PROCÉDÉ POUR SA PRÉPARATION
Publication
Application
Priority
- CZ 2015277 A 20150424
- CZ 2016226 A 20160419
- CZ 2016000048 W 20160420
Abstract (en)
[origin: WO2016169533A1] The invention relates to a solvate of apremilast with tetrahydrofuran - THF of formula 1, wherein the molar ratio of apremilast and THF is 2:1. The THF solvate of apremilast exhibits the characteristic melting point of 79.4°C. Another aspect provides a process for preparing the THF solvate of apremilast. An alternative process for preparing a solvate of apremilast with tetrahydrofuran comprises a reaction of (S)-1-(3-ethoxy-4-methoxyphenyl)-2- (methylsulfonyl)-ethylamine of formula (S)-3 with 3-acetamidophtalic anhydride of formula 5 in a mixture of tetrahydrofuran and an acid, or a reaction of a diastereoisomeric salt of (S)-1- (3-ethoxy-4-memoxyphenyl)-2-(methylsulfonyl)-ethylamine with tartaric acid or their derivatives of formula (S-6) with a base, producing (S)-1-(3-ethoxy-4-methoxyphenyl)-2- (methylsulfonyl)-ethylamine of formula (S)-3, and its reaction with 3-acetamidophtalic anhydride of formula 5 in a mixture of tetrahydrofuran and an acid. Another aspect provides a pharmaceutical composition comprising the THF solvate of apremilast and at least one pharmaceutically acceptable excipient selected from the group of lactose, microcrystalline cellulose, sodium crosscarmellose, and magnesium stearate.
IPC 8 full level
C07D 209/48 (2006.01); A61K 31/4035 (2006.01); A61P 29/00 (2006.01)
CPC (source: EP)
A61P 29/00 (2017.12); C07D 209/48 (2013.01)
Citation (search report)
See references of WO 2016169533A1
Designated contracting state (EPC)
AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR
Designated extension state (EPC)
BA ME
DOCDB simple family (publication)
DOCDB simple family (application)
CZ 2016000048 W 20160420; EP 16725347 A 20160420