Amorphous ciclesonide

• US 20100120737A1
• Filed: 11/10/2008
• Published: 05/13/2010
• Est. Priority Date: 11/10/2008
• Status: Abandoned Application

• Current Assignee: Takeda GmbH (Takeda Pharmaceutical Company Limited)
• Original Assignee: Takeda GmbH (Takeda Pharmaceutical Company Limited)
• Inventors: Zimmermann, Peter, Volz, Jurgen, Schmidt, Beate, Feth, Martin, Hummel, Rolf-Peter
• Application Number:
  US12/292,045
• Publication Number:
  US 20100120737A1
• Time in Patent Office: Days
• US Class Current: 514/181
• CPC Class Codes: A61P 25/00 Drugs for disorders of the nervous system
• CPC Class Codes: C07D 317/70 condensed with ring systems containing two or more relevant rings

Abstract

The present invention relates to amorphous ciclesonide, methods to prepare the same, pharmaceutical compositions comprising amorphous ciclesonide as active ingredient, and methods of treatment using amorphous ciclesonide.

Claims

1. The compound of formula I

(ciclesonide) or a pharmaceutically acceptable solvate thereof, wherein more than 50% (w/w) of said compound is in amorphous form.

2. The compound according to claim 1, wherein more than 95% (w/w) of said compound is in amorphous form.

3. The compound of claim 1, characterized by an X-ray diffraction pattern devoid of Bragg reflexes at 2Θ

=6.8°

+/−

0.3°

, 14.4°

+/−

0.3°

, 14.9°

+/−

0.3°

, 16.8°

+/−

0.3°

, 17.4°

+/−

0.3°

, and 18.3°

+/−

0.3°

which are present in the powder X-ray diffraction pattern of crystalline ciclesonide obtainable when using the Kα

₁ line with a wavelength of 1.54056 Å

of a copper X-ray tube as radiation source.

4. The compound of claim 1, characterized by a FT-Raman spectrum having a signal intensity ratio of I_{787 cm−}

1/I<sub>803 cm−

1</sub>=1.0+/−

0.2.

5. The compound of claim 1, characterized by a DSC scan having an exothermal recrystallization signals below the melting point of crystalline ciclesonide.

6. The compound of claim 1, characterized by a solubility in water at 37°

C. after 20 min of at least 150 μ

g/l.

7. The compound of claim 1, characterized by a solubility in water at 37°

C. after 20 min of at least 300 μ

g/l.

8. The compound of claim 1, characterized by a solubility in water at 37°

C. after 1 h of at least 150 μ

g/l.

9. The compound of claim 1, characterized by a solubility in water at 37°

C. after 1 h of at least 300 μ

g/l.

10. A process for preparing the compound according to claim 1, comprising the steps of:

a. providing a solution of the compound of formula I or a pharmaceutically acceptable solvate thereof,

b. quench cooling the solution of step (a), and

c. lyophilizing the quench cooled solution.

11. A process for preparing the compound according to claim 1, comprising the steps of:

a. providing a solution of the compound of formula I or a pharmaceutically acceptable solvate thereof, and

b. spray drying the solution of step (a).

12. The process according to claim 10, comprising the use of a solvent for preparing the solution of the compound of formula I or a pharmaceutically acceptable solvate thereof, the solvent being selected from tert-butanol and dioxan.

13. A process for preparing the compound according to claim 1, comprising the step of milling crystalline ciclesonide.

14. Amorphous form of the compound of formula I or a pharmaceutically acceptable solvate thereof, obtainable by a process according to claim 10.

15. Amorphous form of the compound of formula I or a pharmaceutically acceptable solvate thereof, obtained by a process according to claim 10.

16. A pharmaceutical composition, comprising a compound or a pharmaceutically acceptable solvate thereof according to claim 1 as active ingredient.

20. A method of treating a respiratory disease in a patient comprising administering a compound according to claim 1 or a pharmaceutically acceptable solvate thereof to a patient in need thereof.

17. (canceled)

18. (canceled)

19. (canceled)