Acid addition salts of benzimidazole derivative
The present invention relates to a pidolate salt and malate salt of a compound represented by a formula 1 with an excellent liquid-phase stability, solid-phase stability, water solubility, precipitation stability and hygroscopicity all together as a compound for preventing and treating diseases mediated by an acid pump antagonistic activity, as well as a method for preparing the same.
1. A pidolate salt of a compound represented by Formula 1, prepared by a process comprising:
a) dissolving a compound represented by Formula 1 and pyroglutamic acid in an organic solvent, thereby creating a solution;
b) concentrating the solution under decompression to precipitate a solid, then adding a co-solvent and stirring; and
c) filtering out and drying the precipitated solid:
2. The method of 1 , wherein the organic solvent is added in a volume 5 to 20 times (volume/weight) compared to the amount of compound represented by Formula 1.
3. The method of claim 1 , wherein the organic solvent is methanol.
4. The method of claim 3 , wherein the methanol is added in a volume 5 to 20 times (volume/weight) compared to the amount of compound represented by Formula 1.
5. The method of claim 4 , wherein the methanol is added in a volume 10 times (volume/weight) compared to the amount of compound represented by Formula 1.
6. The method of claim 1 , wherein the co-solvent is a mixed solution of acetone and ethyl acetate.
7. The method of claim 6 , wherein the ratio of acetone to ethyl acetate is 1:4 (v/v).
8. The method of claim 6 , wherein the mixed solution of acetone and ethyl acetate is added in a volume 5 to 20 times (volume/weight) compared to the amount of compound represented by Formula 1.
9. The method of claim 8 , wherein the mixed solution of acetone and ethyl acetate is added in a volume 5 times (volume/weight) compared to the amount of compound represented by Formula 1.
10. The method of claim 1 , wherein the pyroglutamic acid is L-pyroglutamic acid.
11. A malate salt of a compound represented by Formula 1, prepared by a process comprising:
a) dissolving a compound represented by Formula 1 and malic acid in an organic solvent, thereby creating a solution;
b) concentrating the solution under decompression to precipitate a solid, then adding a co-solvent and stirring; and
c) filtering out and drying the precipitated solid:
12. The method of 11 , wherein the organic solvent is added in a volume 5 to 20 times (volume/weight) compared to the amount of compound represented by Formula 1.
13. The method of claim 11 , wherein the organic solvent is methanol.
14. The method of claim 13 , wherein the methanol is added in a volume 5 to 20 times (volume/weight) compared to the amount of compound represented by Formula 1.
15. The method of claim 14 , wherein the methanol is added in a volume 10 times (volume/weight) compared to the amount of compound represented by Formula 1.
16. The method of claim 11 , wherein the co-solvent is a mixed solution of acetone and ethyl acetate.
17. The method of claim 16 , wherein the ratio of acetone to ethyl acetate is 1:4 (v/v).
18. The method of claim 16 , wherein the mixed solution of acetone and ethyl acetate is added in a volume 5 to 20 times (volume/weight) compared to the amount of compound represented by Formula 1.
19. The method of claim 18 , wherein the mixed solution of acetone and ethyl acetate is added in a volume 5 times (volume/weight) compared to the amount of compound represented by Formula 1.
20. The method of claim 11 , wherein the malic acid is L-malic acid.