Malate salts, and polymorphs of (3S,5S)-7-[3-amino-5-methyl-piperidinyl]-1-cyclopropyl-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
View Patent ↗The present invention is directed to malate salts of (3S,5S)-7-[3-amino-5-methyl-piperidinyl]-1-cyclopropyl-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid, and its polymorphs. The present invention is also directed to pharmaceutical compositions comprising the described salts and polymorphs.
1. A D,L-malate hemi-hydrate salt of (3S,5S)-7-[3-amino-5-methyl-piperidinyl]-1-cyclopropyl-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid.
2. The D,L-malate hemi-hydrate salt according to claim 1 , having an X-ray diffraction pattern substantially in accordance with the pattern of FIG. 1 .
3. The D,L-malate hemi-hydrate salt according to claim 1 , having a solid-state 13 C NMR spectrum substantially in accordance with the pattern of FIG. 4 .
4. The D,L-malate hemi-hydrate salt according to claim 1 , having an infrared spectrum pattern substantially in accordance with the pattern of FIG. 9 .
5. The D,L-malate hemi-hydrate salt according to claim 2 , having characteristic X-ray diffraction peaks at about 10.7, about 11.98 and about 12.5 degrees 2 theta.
6. A D-malate hydrate salt of (3S,5S)-7-[3-amino-5-methyl-piperidinyl]-1-cyclopropyl-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid having an X-ray diffraction pattern substantially in accordance with the pattern of FIG. 2 .
7. An L-malate hydrate salt of (3S,5S)-7-[3-amino-5-methyl-piperidinyl]-1-cyclopropyl-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid having an X-ray diffraction pattern substantially in accordance with the pattern of FIG. 3 .
8. A D-malate anhydrate salt of (3S,5S)-7-[3-amino-5-methyl-piperidinyl]-1-cyclopropyl-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid having a solid-state 13 C NMR spectrum substantially in accordance with the pattern of FIG. 7 .
9. An L-malate anhydrate salt of (3S,5S)-7-[3-amino-5-methyl-piperidinyl]-1-cyclopropyl-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid having a solid-state 13 C NMR spectrum substantially in accordance with the pattern of FIG. 8 .
10. The D-malate hydrate salt according to claim 6 , having a solid-state 13 C NMR spectrum substantially in accordance with the pattern of FIG. 5 .
11. The D-malate hydrate salt according to claim 6 , having an infrared spectrum pattern substantially in accordance with the pattern of FIG. 10 .
12. The D-malate hydrate salt according to claim 6 , having characteristic X-ray diffraction peaks at about 9.3, about 12.1 and about 22.6 degrees 2 theta.
13. The L-malate hydrate salt according to claim 7 , having a solid-state 13 C NMR spectrum substantially in accordance with the pattern of FIG. 6 .
14. The L-malate hydrate salt according to claim 7 , having an infrared spectrum pattern substantially in accordance with the pattern of FIG. 11 .
15. The L-malate hydrate salt according to claim 7 , having characteristic X-ray diffraction peaks at about 9.5, about 11.7 and about 12.3 degrees 2 theta.
16. The D-malate anhydrate salt according to claim 8 , having an infrared spectrum pattern substantially in accordance with the pattern of FIG. 12 .
17. The L-malate anhydrate salt according to claim 9 , having an infrared spectrum pattern substantially in accordance with the pattern of FIG. 13 .