HIGHLY FLUORINATED OILS AND SURFACTANTS AND METHODS OF MAKING AND USING SAME

• US 20090264397A1
• Filed: 03/26/2007
• Published: 10/22/2009
• Est. Priority Date: 03/24/2006
• Status: Active Grant

• Current Assignee: University of Utah Research Foundation (State of Utah)
• Original Assignee: University of Utah Research Foundation (State of Utah)
• Inventors: Yu, Yihua, Jiang, Zhong-Xing
• Granted Patent: US 8,252,778 B2
• Time in Patent Office: Days
• US Class Current: 514/183
• CPC Class Codes: A61K 41/0038 Radiosensitizing, i.e. administration of pharmaceutical agents that enhance the effect of radiotherapy radiotherapy per se A61N5/10
• CPC Class Codes: A61K 47/6905 the form being a colloid or an emulsion
• CPC Class Codes: A61K 47/6953 the form being a fibre, a textile, a slab or a sheet
• CPC Class Codes: A61K 49/0002 General or multifunctional contrast agents, e.g. chelated agents
• CPC Class Codes: A61K 49/085 conjugated systems
• CPC Class Codes: A61K 49/124 dendrimers, dendrons, hyperbranched compounds
• CPC Class Codes: A61K 49/14 Peptides, e.g. proteins
• CPC Class Codes: A61K 49/1809 Micelles, e.g. phospholipidic or polymeric micelles
• CPC Class Codes: A61K 49/1818 particles, e.g. uncoated or non-functionalised microparticles or nanoparticles
• CPC Class Codes: A61K 51/065 conjugates with carriers being macromolecules
• CPC Class Codes: A61K 51/122 Microemulsions, nanoemulsions
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: B82Y 5/00 Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
• CPC Class Codes: C08G 83/003 Dendrimers
• CPC Class Codes: C08G 83/004 After treatment of dendrimers

Abstract

Disclosed are compounds comprising the structure:

In one aspect, the compounds exhibit maximum symmetric branching. Also disclosed are bilayers, micelles, coatings, and nanoparticles comprising the disclosed compounds. Also disclosed are processes for the preparation of the disclosed compounds and methods of using the disclosed compounds. Also disclosed are highly fluorinated dendrons and methods for making same. Also disclosed are methods for Fluorous Mixture Synthesis and tagging. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

Claims

1. A compound comprising the structure:

2. A compound of claim 1, wherein p is 2, 3, 4, or 5.

3. A compound of claim 1, wherein R₁₁, R₁₂, R₁₃, R₂₁, R₂₂, R₂₃, R₃₁, R₃₂, and R₃₃ are CF₃.

55. The method of claim 101, comprising the steps of:

a. complexing a radionuclide with a compound of claim 1; and

b. administering the complex to a mammal in an amount effective for radiotherapy.

57. The method of claim 101, comprising the steps of:

a. complexing a metal ion with a compound of claim 1; and

b. administering the complex to a subject in an amount effective for detection by ¹H MRI.

65. The compound of claim 1, comprising the structure:

101. A delivery method comprising the steps of:

a. complexing a payload with one or more compounds of claim 1; and

b. administering the complex to a mammal in an effective amount.

4. A compound of claim 0, comprising the structure:

5. A compound of claim 0, wherein R₁₁, R₁₂, R₁₃, R₂₁, R₂₂, R₂₃, R₃₁, R₃₂, and R₃₃ are CF₃.

6. A compound of claim 0, comprising the structure:

10. A compound of claim 6, wherein R₁₁, R₁₂, R₁₃, R₂₁, R₂₂, R₂₃, R₃₁, R₃₂, and R₃₃ are CF₃.

11. A compound of claim 6, wherein the compound is a surfactant.

12. A compound of claim 6, comprising the structure:

13. A compound of claim 6, wherein the compound is an oil.

14. A compound of claim 6, comprising the structure:

7-9. -9. (canceled)

15. A compound of claim 0, wherein the compound exhibits maximum symmetric branching.

16-20. -20. (canceled)

21. A process for the preparation of a compound comprising the structure:

34. The process of claim 21, wherein the compound comprises the structure:

22-33. -33. (canceled)

35. The process of claim 0, wherein R is CF₃.

36. The process of claim 0, wherein n is an integer from 4 to 12.

37-54. -54. (canceled)

56. (canceled)

58-64. -64. (canceled)

66-100. -100. (canceled)