Derivatives of mesalazine, process of their preparation and their use in the treatment of intestinal inflammatory diseases
AssigneeSofar SPA
InventorCarla Labruzzo
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Abstract
The present invention refers to the compounds corresponding to the following general formulas (I) and (Ia): wherein: R═C4-C8 alkanoyl; and X═NH—R1 where R1═H, or an amine protecting group; and/or the pharmaceutically acceptable salts thereof. A further object of the present invention is represented by the use of the compounds of formula (Ia), in particular 5-amino-2-(butyryloxy)benzoic acid and/or pharmaceutically acceptable salts thereof, as a medicament and by the use thereof for the treatment of intestinal inflammatory diseases.
Claims58
A compound of formula (I):
- wherein:
- R═C4-C8 alkanoyl;
- and
- X═NH—R1
- where R1═H, or an amine protecting group;
- and/or the pharmaceutically acceptable salts thereof.
5-amino-2-(butyryloxy)benzoic acid and/or pharmaceutically acceptable salts thereof.
A process for the preparation of the compound of formula (Ia)
- comprising the following steps:
- a) protection of 5-ASA with an amine protecting group to obtain the compound of formula (II′);
- b) acylation of the hydroxyl group of the compound of formula (II′) to obtain the compound of formula (III′);
- and
- c) deprotection of the amino group of the compound of formula (III′);
- wherein:
- R═C4-C8 alkanoyl;
- and R1 is an amine protecting group.
A process for the preparation of 5-amino-2-(butyryloxy)benzoic acid hydrochloride comprising the following steps:
- a) protection of 5-ASA as a Boc-derivative to obtain the compound (II);
- b) butyrylation of the hydroxyl group of the compound (II) to obtain the compound (III);
- and
- c) deprotection of the amino group of the compound (III).
A process for the preparation of the compound of formula (Ia)
- comprising the following steps:
- a) acylation of the hydroxyl group of the compound of formula (V′)
- to obtain the compound of formula (VI′);
- and
- b) hydrogenation of the nitro group of the compound of formula (VI′);
- wherein:
- R═C4-C8 alkanoyl.
A process for the synthesis of 5-amino-2-(butyryloxy)benzoic acid comprising the following steps:
- a) butyrylation of the compound of formula (V′)
- to obtain the compound (VI);
- and
- b) hydrogenation of the compound (VI).
A compound of formula (Ib):
Dependencies are inferred from the claim text.