Lercanidipine salts
AssigneeRecordati Ireland Limited
InventorsAmedeo Leonardi, Gianni Motta, Markus von Raumer
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Abstract
The present invention relates to new addition salts of lercanidipine comprising lercanidipine and an acid counterion wherein the acid counterion is selected from the group consisting of: (i) inorganic acids, (ii) sulfonic acids, (iii) monocarboxylic acids, (iv) dicarboxylic acids, (v) tricarboxylic acids, and (vi) aromatic sulfonimides, with the proviso that said acid counterion is not hydrochloric acid.
Claims34
An acid addition salt of:
- (a) lercanidipine, and
- (b) an acid counterion of an acid selected from the group consisting of:
- (i) sulfonic acids, (ii) monocarboxylic acids, and (iii) aromatic sulfonimides, wherein the sulfonic acids are selected from the group consisting of benzenesulfonic acid and naphthalene-1,5-disulfonic acid.
An acid addition salt of:
- (a) lercanidipine, and
- (b) an acid counterion of an acid selected from the group consisting of:
- (i) benzenesulfonic acid, and (ii) napthalene-1,5-disulfonic acid.
A crystalline lercanidipine napadisylate having a x-ray diffraction pattern comprising four or more peaks with a 2θ value selected from the group consisting of:
- 8.35, 10.12, 11.14, 11.81, 14.29, 15.60, 16.75, 20.98, 21.34, 21.62, 22.44, 23.21, 24.19, 28.82 and 29.52.
A crystalline lercanidipine besylate having a x-ray diffraction pattern comprising four or more peaks with a 2θ value selected from the group consisting of:
- 6.31, 10.92, 12.31, 12.77, 13.50, 13.73, 14.23, 15.52, 16.40, 17.12, 17.92, 18.30, 18.55, 19.00, 19.78, 20.08, 20.35, 21.24, 22.07, 22.47, 23.22, 23.45, 24.05, and 28.73.
A method for preparing lercanidipine crystalline salts, comprising the steps of:
- (b) reacting methyl 1,1,N-trimethyl-N-(3,3-diphenylpropyl)-2-aminoethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3,5-dicarboxylate, with an acid counterion in an organic solvent to form a lercanidipine salt, wherein said acid counterion is selected from the group consisting of:
- L-lactic acid, cinnamic acid, benzenesulphonic acid, and naphthalene- 1,5-disulphonic acid;
- (c) removing said organic solvent, thereby isolating the resultant lercanidipine salt;
- and
- (d) recrystallizing said lercanidipine salt in at least one of two successive steps, regardless of sequence, from a solution of said lercanidipine salt in;
- (i) an aprotic solvent;
- and
- (ii) a protic solvent;
- thereby isolating methyl 1,1, N-trimethyl-N-(3,3-diphenylpropyl)-2-aminoethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3,5-dicarboxylate as a substantially pure crystalline salt.
Dependencies are inferred from the claim text.