Crystalline forms of the di-sodium salt of N-(5-Chlorosalicyloyl)-8-aminocaprylic acid
View Patent ↗The present invention relates to crystalline polymorphic forms of the di-sodium salt of N-(5-chlorosalicyloyl)-8-aminocaprylic acid, pharmaceutical compositions containing the same, methods of preparing the same, and methods for facilitating the delivery of active agents with the same.
1. A crystalline monohydrate of the disodium salt of N-(5-chlorosalicyloyl)-8-aminocaprylic acid exhibiting an X-ray powder diffraction pattern having at least one peak in degrees 2θ±0.2° 2θ selected from 7.2, 18.2, and 24.7.
2. A pharmaceutical composition comprising the crystalline monohydrate of claim 1 and a biologically active agent.
3. The pharmaceutical composition of claim 2 , wherein the biologically active agent is calcitonin.
4. The pharmaceutical composition of claim 2 , wherein the biologically active agent is parathyroid hormone.
5. The pharmaceutical composition of claim 2 , wherein the biologically active agent is insulin.
6. The pharmaceutical composition of claim 2 , wherein the biologically active agent is a growth hormone.
7. A process for preparing the disodium salt of N-(5-chlorosalicyloyl)-8-aminocaprylic acid according to claim 1 comprising the steps of:
(a) dissolving the disodium salt of N-(5-chlorosalicyloyl)-8-aminocaprylic acid in methyl ethyl ketone at an elevated temperature; and
(b) cooling the methyl ethyl ketone solution of step (a) to yield the disodium salt of N-(5-chlorosalicyloyl)-8-aminocaprylic acid of claim 1 .
8. A crystalline monohydrate of the disodium salt of N-(5-chlorosalicyloyl)-8-aminocaprylic acid exhibiting an X-ray powder diffraction pattern having peaks in degrees 2θ±0.2° 2θ at 7.2 and 18.2.
9. A pharmaceutical composition comprising the crystalline monohydrate of claim 8 and a biologically active agent.
10. The pharmaceutical composition of claim 9 , wherein the biologically active agent is calcitonin.
11. The pharmaceutical composition of claim 9 , wherein the biologically active agent is parathyroid hormone.
12. The pharmaceutical composition of claim 9 , wherein the biologically active agent is insulin.
13. The pharmaceutical composition of claim 9 , wherein the biologically active agent is a growth hormone.
14. A crystalline monohydrate of the disodium salt of N-(5-chlorosalicyloyl)-8-aminocaprylic acid exhibiting an X-ray powder diffraction pattern having peaks in degrees 2θ±0.2° 2θ at 7.2, 18.2, and 24.7.
15. A pharmaceutical composition comprising the crystalline monohydrate of claim 14 and a biologically active agent.
16. The pharmaceutical composition of claim 15 , wherein the biologically active agent is calcitonin.
17. The pharmaceutical composition of claim 15 , wherein the biologically active agent is parathyroid hormone.
18. The pharmaceutical composition of claim 15 , wherein the biologically active agent is insulin.
19. The pharmaceutical composition of claim 15 , wherein the biologically active agent is a growth hormone.