Calcium salts of indole derived statins

C - Chemistry – Metallurgy – 07 – D

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C07D 209/24 (2006.01) A61K 31/405 (2006.01) C07D 209/22 (2006.01)

Patent

CA 2486557

The present invention provides calcium salts of indole derived statins of the formula (IA) wherein R1, is alkyl, cycloalkyl or aralkyl; R2, R3 and R4 are independently hydrogen, halogen or alkyl; R5 and R6 are independently hydrogen, halogen, alkyl, cycloalkyl, aralkyl, alkoxy or aralkoxy; and the hydroxyl group at the 3~position is in the R-configuration and at the 5position in the S-configuration; or an enantiomer thereof; or a hydrate thereof; as obtainable by the methods of the present invention. More specifically, the invention provides a calcium salt of formula (IA) wherein R1, is isopropyl, R2 is fluorine and R3, R4 R5 and R6 are hydrogen, designated herein as Fluvastatin calcium, in a highly crystalline form. Furthermore, the present invention is directed to methods for the preparation of the crystalline Fluvastatin calcium, and to pharmaceutical compositions comprising the crystalline form.

La présente invention concerne des sels de calcium de statines dérivées d'indole de formule (IA), dans laquelle R¿1? représente alkyle, cycloalkyle ou aralkyle ; R¿2?, R¿3? et R¿4? désignent indépendamment hydrogène, halogène ou alkyle ; R¿5? et R¿6? désignent indépendamment hydrogène, halogène, alkyle, cycloalkyle, aralkyle, alcoxy ou aralcoxy et le groupe hydroxyle en position 3 est en configuration R et en position 5 en configuration S, ou un énantiomère ou hydrate de ces sels obtenu selon les procédés de la présente invention. Cette invention concerne plus spécifiquement un sel de calcium de formule (IA), dans laquelle R¿1? représente isopropyle, R¿2? représente fluor et R¿3?, R¿4?, R¿5?, et R¿6? représentent hydrogène, appelé calcium de fluvastatine, sous une forme hautement cristalline. La présente invention concerne également des procédés de préparation de calcium de fluvastatine cristallin ainsi que des compositions pharmaceutiques contenant cette forme cristalline.

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