Lipid soluble steroid prodrugs

• US 6,444,660 B1
• Filed: 02/03/2000
• Issued: 09/03/2002
• Est. Priority Date: 05/06/1997
• Status: Expired due to Fees

• Current Assignee: Cerevast Therapeutics, Inc.
• Original Assignee: Imarx Therapeutics, Inc. (Sycamore Entertainment Group, Inc.)
• Inventors: Shen, DeKang, Unger, Evan C.
• Primary Examiner(s): Badio, Barbara P.
• Application Number:
  US09/496,761
• Time in Patent Office: 943 Days
• Field of Search: 552/574, 514/180
• US Class Current: 514/180
• CPC Class Codes: A61K 41/0028 Disruption, e.g. by heat or ultrasounds, sonophysical or sonochemical activation, e.g. thermosensitive or heat-sensitive liposomes, disruption of calculi with a medicinal preparation and ultrasounds
• CPC Class Codes: A61K 47/544 Phospholipids
• CPC Class Codes: A61K 49/223 Microbubbles, hollow microspheres, free gas bubbles, gas microspheres
• CPC Class Codes: A61K 9/1271 Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers liposome as conjugate A61K47/6911

Abstract

The present invention is directed to novel lipid soluble steroid prodrugs, compositions comprising steroid prodrugs, and uses of the same.

Claims

1. A method of delivering a steroid to a patient in need thereof comprising administering to a patient a composition comprising a gas, a gaseous precursor, or a gas and a gaseous precursor, and a compound of formula (I):

2. A method of claim 1, wherein said administration is intravenous.

3. A method of claim 1, wherein said administration is topical.

4. A method of claim 1, wherein said lipid moiety forms a vesicle.

5. A method of claim 1, wherein said lipid moiety is non-vesicular.

6. A method of claim 1, wherein said composition further comprises a fluorinated liquid.

7. A method of claim 6, wherein said fluorinated liquid is selected from the group consisting of perfluorooctylbromide, perfluorooctyliodide, perfluorotripropylamine, perfluorotributylamine, perfluorodecalin and perfluorododecalin.

8. A method of claim 1, wherein the gas or gaseous precursor is selected from the group consisting of nitrogen, sulfur hexafluoride, a perfluorocarbon and a perfluoroether.

9. A method of claim 8, wherein the perfluorocarbon is selected from the group consisting of perfluoromethane, perfluoroethane, perfluoropropane, perfluorobutane, perfluoropentane, perfluorohexane, perfluoroheptane, perfluorooctane, perfluorononane, perfluorocyclobutane, perfluorocyclopropane and perfluorocyclopentane.

10. A method of claim 8, wherein the pertluoroether is selected from the group consisting of perfluorobutylmethylether, perfluoromethylpentylether, perfluorotetrahydropyran and pertluoromethyltetrahydrofuiran.

11. A method of claim 1, wherein X is succinate.

12. A method of claim 1, where L is dipalmitoylglyceryl.

13. A method of claim 1, wherein said compound of formula (I) is: