EP 0471820 A1 19920226 - DIASTEREOISOMERIC COMPOUNDS DERIVED FROM TETRAHYDROFOLIC ACID, PROCESS FOR THEIR PREPARATION AND USE IN THE SYNTHESIS OF DIASTEREOISOMERS 6S AND 6R OF REDUCED FOLATES.
Title (en)
DIASTEREOISOMERIC COMPOUNDS DERIVED FROM TETRAHYDROFOLIC ACID, PROCESS FOR THEIR PREPARATION AND USE IN THE SYNTHESIS OF DIASTEREOISOMERS 6S AND 6R OF REDUCED FOLATES.
Title (de)
VON TETRAHYDROFOLSÄURE ABGELEITETE DIASTEREOMERE VERBINDUNGEN, VERFAHREN ZU IHRER HERSTELLUNG UND VERWENDUNG IN DER SYNTHESE VON 6S- UND 6R-DIASTEREOMEREN VON REDUZIERTEN FOLATEN.
Title (fr)
COMPOSES DIASTEREOISOMERES DERIVANT DE L'ACIDE TETRAHYDROFOLIQUE, PROCEDE DE PREPARATION ET UTILISATION DANS LA SYNTHESE DE DIASTEREOISOMERES 6S ET 6R DE FOLATES REDUITS.
Publication
Application
Priority
FR 9003032 A 19900309
Abstract (en)
[origin: WO9113890A2] The present invention concerns a new process for preparing diastereoisomers derived from tetrahydrofolic acid. By the reaction of (i) (6RS)-folinic acid or one of its salts or (ii) 5,10-methenyl-5,6,7,8-tetrahydrofolic acid with HCOOH at a pH of 2.0-2.6, a precipitate is obtained consisting of a mixture of two diastereoisomers with an orthoamide structure and the formulae (III) and (IV) where R is the p-benzoyl-(L)-glutamic radical, in a molar ratio (IV/III) of about 7/3, with compound (III) of "natural" configuration and compound (IV) of "non-natural" configuration. Pure compound (IV) is isolated from said precipitate and pure compound (III) from the corresponding filtrate. From compound (III) and (IV) are prepared the diastereoisomers of the reduced folates and their natural and non-natural configuraton salts.
Abstract (fr)
La présente invention à trait à un nouveau procédé de préparation de diastéréoisomères dérivant de l'acide tétrahydrofolique. Par réaction de (i) l'acide (6RS)-folinique ou de l'un de ses sels, ou (ii) de l'acide 5,10-méthényl-5,6,7,8-tétrahydrofolique, avec HCOOH à pH 2,0-2,6 on obtient un précipité constitué par un mélange de deux diastéréoisomères de structure orthoamide et de formules: (III) et (IV) où R représente le reste p-benzoyl-(L)-glutamique, dans un rapport molaire (IV/III) d'environ 7/3, le composé (III) étant de configuration dite naturelle et le composé (IV) de configuration dite non-naturelle. On isole le composé (IV) pur dudit précipité, et le composé (III) pur du filtrat correspondant. A partir du composé (III) et respectivement (IV) on prépare les diastéréoisomères des folates réduits et de leurs sels de configuration naturelle, et respectivement non-naturelle.
IPC 1-7
IPC 8 full level
A61K 31/495 (2006.01); A61P 35/00 (2006.01); C07D 475/04 (2006.01); C07D 487/14 (2006.01); C07D 498/22 (2006.01)
CPC (source: EP US)
A61P 35/00 (2017.12 - EP); C07D 475/04 (2013.01 - EP US); C07D 487/14 (2013.01 - EP US)
Citation (search report)
See references of WO 9113890A2
Designated contracting state (EPC)
AT BE CH DE DK ES FR GB GR IT LI LU NL SE
DOCDB simple family (publication)
WO 9113890 A2 19910919; WO 9113890 A3 19911114; AU 7492591 A 19911010; CA 2056433 A1 19910910; EP 0471820 A1 19920226; FI 915254 A0 19911107; FR 2659330 A1 19910913; FR 2659330 B1 19940211; JP H04507103 A 19921210; US 5239074 A 19930824
DOCDB simple family (application)
FR 9100185 W 19910308; AU 7492591 A 19910308; CA 2056433 A 19910308; EP 91905831 A 19910308; FI 915254 A 19911107; FR 9003032 A 19900309; JP 50578991 A 19910308; US 78442291 A 19911106