Prodrugs comprising fluorinated amphiphiles

• US 6,028,066 A
• Filed: 07/02/1997
• Issued: 02/22/2000
• Est. Priority Date: 05/06/1997
• Status: Expired due to Fees

• Current Assignee: Imarx Therapeutics, Inc. (Sycamore Entertainment Group, Inc.)
• Original Assignee: Imarx Pharmaceutical Corp. (Sycamore Entertainment Group, Inc.)
• Inventors: Unger, Evan C.
• Primary Examiner(s): Dees, Jose' G.
• Assistant Examiner(s): BADIO, BARBARA P
• Application Number:
  US08/887,215
• Time in Patent Office: 965 Days
• Field of Search: 552/506, 552/507, 552/566, 514/169, 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 describes, inter alia, novel prodrugs comprising fluorinated amphiphiles, compositions comprising the novel prodrugs, and methods of use of the prodrugs and compositions.

Claims

1. A compound of the formula (I):

space="preserve" listing-type="equation">R--(X).sub.p --D (I)

wherein;

R is a fluorinated amphiphilic moiety having the formula ##STR21## X is a linking group having a carbonyl moiety;

m is an integer of from 0 to 18 and n is an integer of from 1 to 12;

p is 1; and

D is a steroid, wherein X is attached to R via the --OP(O₂^-)O-- moiety.

2. The compound of claim 1, wherein the steroid is dexamethasone.

3. The compound of claim 1 wherein m is 7 and n is 6.

4. A composition comprising, in an aqueous carrier, a compound of the formula (I):

space="preserve" listing-type="equation">R--(X).sub.p --D (I)

wherein;

R is a fluorinated amphiphilic moiety having the formula ##STR22## X is a linking group having a carbonyl moiety;

m is an integer of from 0 to 18 and n is an integer of from 1 to 12;

p is 1; and

D is a steroid, wherein X is attached to R via the --OP(O₂^-)O-- moiety.

5. The composition of claim 4 wherein m is 7 and n is 6.

6. The composition of claim 4 wherein the steroid is dexamethasone.

7. The composition of claim 4, wherein said fluorinated amphiphilic moiety forms a vesicle.

8. The composition of claim 4, wherein said fluorinated amphiphilic moiety is non-vesicular.