Prostaglandin Based Compositions and Method of Use Thereof

• US 20100166841A1
• Filed: 05/13/2009
• Published: 07/01/2010
• Est. Priority Date: 05/14/2008
• Status: Abandoned Application

• Current Assignee: Peter Thomas Roth Labs, LLC
• Original Assignee: Peter Thomas Roth Labs, LLC
• Inventors: Roth, Peter Thomas, Blake, Bridget
• Application Number:
  US12/465,522
• Publication Number:
  US 20100166841A1
• Time in Patent Office: Days
• US Class Current: 424/450
• CPC Class Codes: A61K 8/365 Hydroxycarboxylic acids; Ketocarboxylic acids
• CPC Class Codes: A61K 8/42 Amides
• CPC Class Codes: A61Q 1/10 for eyes, e.g. eyeliner, mascara
• CPC Class Codes: A61Q 5/00 Preparations for care of the hair

Abstract

The present disclosure sets forth particular prostaglandin based compounds that are relatively more stable in aqueous environments than other such compounds; and further that by complexing such a prostaglandin based compound of the disclosure with an agent, such as cyclodextrin, the prostaglandin based compound may be stabilized and provided in a cosmetic composition that can be used to enhance the appearance of hair.

Claims

1. A topical composition for application to mammalian skin, eyebrow or eyelash comprising

an effective amount of a prostaglandin based compound;

and

optionally, a biologically acceptable carrier,

wherein said prostaglandin based compound is

wherein the dashed bonds represent a single or double bond which can be in the cis or trans configuration,

A is an alkylene or alkenylene radical having from two to six carbon atoms, which radical may be interrupted by one or more oxa radicals and substituted with one or more hydroxy, oxo, alkyloxy or alkylcarboxy groups wherein said alkyl radical comprises from one to six carbon atoms;

B is a cycloalkyl radical having from three to seven carbon atoms, or an aryl radical, selected from the group consisting of hydrocarbyl aryl and heteroaryl radicals having from four to ten carbon atoms wherein the heteroatom is selected from the group consisting of nitrogen, oxygen and sulfur atoms;

X is either —

N(H)CH(CH₂OH)₂ or —

OCH(CH₂OH)₂;

Z is ═

O;

one of R₁ and R₂ is ═

O, —

OH or a —

O(CO)R₃ group, and the other one is —

OH or —

O(CO)R₃, or R₁ is ═

O and R₂ is H, wherein R₃ is a saturated or unsaturated acyclic hydrocarbon group having from 1 to about 20 carbon atoms, or —

(CH₂)mR₄ wherein m is 0 or an integer of from 1 to 10, and R₄ is cycloalkyl radical, having from three to seven carbon atoms, or a hydrocarbyl aryl or heteroaryl radical, or a pharmacologically acceptable acid addition salt thereof.

2. The composition of claim 1, wherein said prostaglandin based compound is either [(2-hydroxy-1-hydroxymethypethyl]-9-oxo-11,15-dihydroxy-17-phenyl-18,19,20-trinor-prosta-5Z,13E-dien-1-oate or 17-phenyl trinor prostaglandin E2 serinol amide.

3. The composition of claim 1, further comprising a stabilizing agent.

4. The composition of claim 3, wherein said stabilizing agent is a cyclodextrin.

5. The composition of claim 4, wherein said cyclodextrin is a selected from the group consisting of α

-cyclodextrin, β

-cyclodextrin, a γ

-cyclodextrin, 2-hydroxypropyl-alpha-cyclodextrin, 2-hydroxypropyl-beta-cyclodextrin, sulfobutyl ether-beta-cyclodextrin, and 2,6-dimethyl-beta cyclodextrin.

6. The composition of claim 3, wherein said stabilizing agent is dextran, dextrin, or pullulan.

7. A liposome comprising the composition of claim 1.

8. The liposome of claim 7, wherein said liposome comprises a phospholipid.

9. The liposome of claim 8, wherein said liposome further comprises retinyl palmitate, ascorbyl palmitate, or tocopheryl acetate.

10. The composition of claim 1, wherein said composition further comprises an alkyl benzoate.

11. The composition of claim 10, wherein said prostaglandin based compound and alkyl benzoate are contacted with an alcohol prior to formulation of the composition.

12. The composition of claim 10, wherein said prostaglandin based compound is provided admixed with said alkyl benzoate.

13. The composition of claim 12, wherein said alkyl benzoate is C_12-15 alkyl benzoate (Cetiol AB®

) or FINSOLV®

TN-O.

14. The composition of claim 1, wherein said composition further comprises a preservative.

15. The composition of claim 1, wherein said composition further comprises a moisturizing agent.

16. A method of enhancing the appearance of at least one property of a subject'"'"'s hair selected from the group consisting of:

luster, sheen, brilliance, gloss, glow, shine, patina, length, thickness, and density;

the method comprising contacting a portion of skin of a subject with the composition of claim 1, wherein said skin is associated with hair follicles and said contacting results in the enhancement of the appearance of the at least one property of the hair of the subject.

17. The method of claim 16, wherein the skin to be contacted is selected from the group consisting of skin associated with an eyelash, skin associated with an eyebrow, skin associated with a scalp, and skin associated with a face of the subject.

18. The method of claim 16, wherein said composition is formulated as an aqueous solution, an ointment, a liniments, a cream, a lotion, a paste, jelly, a shampoo, a rinse, a conditioner, an aerosol, or a spray.

19. The method of claim 16, wherein said contacting is performed at least once a day.

20. The method of claim 19, wherein said contacting is performed for at least 3 months.

21. A kit, the kit comprising one or more of the composition of claim 1, a suitable container for storing the composition, packaging, and directions for using the composition.