Crystalline solid and amorphous forms of (−)-halofenate and methods related thereto

Patent metadata

Field	Value
Publication number	US-9845285-B2
Application number	US-201514957962-A
Country	US
Kind code	B2
Filing date	Dec 3, 2015
Priority date	Apr 20, 2005
Publication date	Dec 19, 2017
Grant date	Dec 19, 2017

Abstract

The present invention provides crystalline solid and amorphous forms of (−)-halofenate. The crystalline solid forms may be used in various pharmaceutical compositions, and are particularly effective for the prevention and/or treatment of conditions associated with blood lipid deposition in a mammal, particularly those diseases related to Type 2 diabetes and hyperlipidemia. The invention also relates to a method for preventing or treating Type 2 diabetes and hyperlipidemia in a mammal comprising the step of administering a therapeutically effective amount of crystalline solid and amorphous forms of (−)-halofenate.

First claim

What is claimed is:

1. A pharmaceutical composition comprising a pharmaceutically acceptable excipient and a therapeutically effective amount of the compound (−)-halofenate in a crystalline solid form A characterized by an X-ray powder diffraction pattern comprising a peak at about 10.8° 2θ and an infrared spectrum comprising at least one peak selected from at about 3322 cm −1 and at about 2886 cm −1 .

2. The pharmaceutical composition of claim 1 where the crystalline solid form A consists of greater than 95% by weight (−)-halofenate and less than 5% by weight of other non-solvent compounds.

3. The pharmaceutical composition of claim 1 where the composition is a solid oral composition.

4. The pharmaceutical composition of claim 3 where the composition is a tablet or capsule.

5. A pharmaceutical composition comprising a pharmaceutically acceptable excipient and a therapeutically effective amount of the compound (−)-halofenate in a crystalline solid form A characterized by an X-ray powder diffraction pattern comprising a peak at about 10.8° 2θ and a Raman spectrum comprising at least one peak selected from at about 3087 cm −1 and at about 1663 cm −1 .

6. The pharmaceutical composition of claim 5 where the crystalline solid form A consists of greater than 95% by weight (−)-halofenate and less than 5% by weight of other non-solvent compounds.

7. The pharmaceutical composition of claim 5 where the composition is a solid oral composition.

8. The pharmaceutical composition of claim 7 where the composition is a tablet or capsule.

9. A pharmaceutical composition comprising a pharmaceutically acceptable excipient and a therapeutically effective amount of the compound (−)-halofenate in a crystalline solid form A characterized by an X-ray powder diffraction pattern comprising a peak at about 10.8° 2θ, an infrared spectrum comprising at least one peak selected from at about 3322 cm −1 and at about 2886 cm −1 , and a Raman spectrum comprising at least one peak selected from at about 3087 cm −1 and at about 1663 cm −1 .

10. The pharmaceutical composition of claim 9 where the crystalline solid form A consists of greater than 95% by weight (−)-halofenate and less than 5% by weight of other non-solvent compounds.

11. The pharmaceutical composition of claim 9 where the composition is a solid oral composition.

12. The pharmaceutical composition of claim 11 where the composition is a tablet or capsule.

13. A pharmaceutical composition comprising a pharmaceutically acceptable excipient and a therapeutically effective amount of the compound (−)-halofenate in a crystalline solid form A characterized by an X-ray powder diffraction pattern comprising peaks at about 10.8° 2θ, about 22.0° 2θ, and about 29.3° 2θ; and an infrared spectrum comprising peaks at about 3322 cm −1 and about 2886 cm −1 .

14. The pharmaceutical composition of claim 13 where the crystalline solid form A consists of greater than 95% by weight (−)-halofenate and less than 5% by weight of other non-solvent compounds.

15. The pharmaceutical composition of claim 13 where the composition is a solid oral composition.

16. The pharmaceutical composition of claim 15 where the composition is a tablet or capsule.

17. A pharmaceutical composition comprising a pharmaceutically acceptable excipient and a therapeutically effective amount of the compound (−)-halofenate in a crystalline solid form A characterized by an X-ray powder diffraction pattern comprising peaks at about 10.8° 2θ, about 22.0° 2θ, and about 29.3° 2θ; and a Raman spectrum comprising peaks at about 3087 cm −1 and about 1663 cm −1 .

18. The pharmaceutical composition of claim 17 where the crystalline solid form A consists of greater than 95% by weight (−)-halofenate and less than 5% by weight of other non-solvent compounds.

19. The pharmaceutical composition of claim 17 where the composition is a solid oral composition.

20. The pharmaceutical composition of claim 19 where the composition is a tablet or capsule.

Assignees

• Cymabay Therapeutics Inc
• Diatex Inc

Inventors

• Daugs Edward D
• Hagen Eric J
• Hanko Jason A
• Louks David H

Classifications

• A61K31/216

  of acids having aromatic rings, e.g. benactizyne, clofibrate · CPC title

• A61P3/06

  Antihyperlipidemics · CPC title

• A61P9/00

  Drugs for disorders of the cardiovascular system · CPC title

• C07C235/78

  the carbon skeleton containing rings · CPC title

• C07B2200/07

  Optical isomers · CPC title