Ester Derivatives of Bimatoprost Compositions and Methods

• US 20130324606A1
• Filed: 02/13/2012
• Published: 12/05/2013
• Est. Priority Date: 02/14/2011
• Status: Abandoned Application

• Current Assignee: Allergan, Inc. (Canada) (Abbvie Incorporated)
• Original Assignee: Allergan, Inc. (Canada) (Abbvie Incorporated)
• Inventors: Woodward, David F., Wang, Jenny W., Poloso, Neil J., Gac, Todd S., Burk, Robert M., Garst, Michael E.
• Application Number:
  US13/985,263
• Publication Number:
  US 20130324606A1
• Time in Patent Office: Days
• US Class Current: 514/546
• CPC Class Codes: A61K 8/42 Amides
• CPC Class Codes: A61P 17/14 for baldness or alopecia
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: A61Q 7/00 Preparations for affecting hair growth
• CPC Class Codes: C07C 235/34 having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
• CPC Class Codes: C07C 2601/08 the ring being saturated
• CPC Class Codes: C07C 405/00 Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
• CPC Class Codes: C07C 405/0041 containing nitrogen

Abstract

Provided herein, inter alia, are prodrugs of bimatoprost, methods of using the same and compositions including the same.

Claims

1. A compound with structure of Formula (I):

2. The compound of claim 1, wherein R^1a, R^2a and R^3a are independently substituted or unsubstituted C₁-C₆ alkyl.

3. The compound of claim 2, wherein R^1a, R^2a and R^3a are independently substituted or unsubstituted C₁-C₃ alkyl.

4. The compound of claim 3, wherein R^1a, R^2a and R^3a are independently substituted or unsubstituted C₁ alkyl.

5. The compound of claim 4, wherein R^1a, R^2a and R^3a are independently methyl.

6. The compound of claim 1, wherein R^1a, R^2a and R^3a are independently substituted or unsubstituted C₃-C₈ cycloalkyl.

7. The compound of claim 6, wherein R^1a, R^2a and R^3a are independently unsubstituted C₃-C₈ cycloalkyl.

8. The compound of claim 1, wherein R^1a, R^2a and R^3a are independently substituted or unsubstituted aryl.

9. The compound of claim 8, wherein R^1a, R^2a and R^3a are independently aryl.

10. The compound of claim 1, wherein R^1a, R^2a and R^3a are independently phenyl.

11. The compound of claim 1, wherein R⁴ is substituted or unsubstituted C₁-C₁₀ alkyl, or substituted or unsubstituted C₃-C₈ cycloalkyl.

12. The compound of claim 11, wherein R⁴ is substituted or unsubstituted C₁-C₆ alkyl.

13. The compound of claim 12, wherein R⁴ is substituted or unsubstituted C₁-C₃ alkyl.

14. The compound of claim 13, wherein R⁴ is substituted or unsubstituted C₂ alkyl.

15. The compound of claim 14, wherein R⁴ is ethyl.

16. The compound of claim 11, wherein R⁴ is substituted or unsubstituted C₃-C₈ cycloalkyl.

17. The compound of claim 1, wherein R⁵ is hydrogen.

18. The compound of claim 1, having the structure of Formula (IVa):

19. The compound of claim 1, having the structure of Formula (IIIb):

20. The compound of claim 1, having the structure of Formula (IVb):

21. A method for inducing hair growth in a human comprising administering to a subject in need thereof a therapeutically effective amount of a compound with structure of Formula (I):

22. The method of claim 21, wherein said subject suffers from alopecia.

23. The method of claim 21, wherein said subject is in need of hair growth of the cilia, the supercilia, scalp pili, or body pili.

24. The method of claim 21, wherein said administering is topical administering.

25. The method of claim 24, wherein said administering is topical epidermal administering.

26. The method of claim 21, wherein said compound is