Lipid-drug conjugates for drug delivery

• US 20100240883A1
• Filed: 03/17/2010
• Published: 09/23/2010
• Est. Priority Date: 03/18/2009
• Status: Abandoned Application

• Current Assignee: Brian Charles Keller, Nian Wu
• Original Assignee: Brian Charles Keller, Nian Wu
• Inventors: Keller, Brian Charles, Wu, Nian
• Application Number:
  US12/661,465
• Publication Number:
  US 20100240883A1
• Time in Patent Office: Days
• US Class Current: 536/28.510
• CPC Class Codes: C07C 237/04 the carbon skeleton being acyclic and saturated
• CPC Class Codes: C07C 237/22 having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated peptides C07K
• CPC Class Codes: C07C 257/20 having nitrogen atoms of amidino groups acylated
• CPC Class Codes: C07C 2601/14 The ring being saturated
• CPC Class Codes: C07C 2603/74 Adamantanes
• CPC Class Codes: C07D 207/46 with hetero atoms directly attached to the ring nitrogen atom
• CPC Class Codes: C07D 411/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07H 13/04 having the esterifying carboxyl radicals attached to acyclic carbon atoms
• CPC Class Codes: C07H 13/06 Fatty acids
• CPC Class Codes: C07H 15/24 Condensed ring systems having three or more rings
• CPC Class Codes: C07H 19/073 with 2-deoxyribosyl as the saccharide radical
• CPC Class Codes: C07H 5/06 Aminosugars

Abstract

New prodrugs are derived from highly water soluble parent drugs that exist as primary or secondary amines in their parent form. Lipophilic carrier groups are bonded to the parent drug via an amide linkage with additional linker elements between the amide group and the carrier group.

Claims

1. A prodrug of a parent drug having either a primary or secondary amine, the prodrug represented by the formula:

2. The prodrug of claim 1, where the parent drug has an octanol-water distribution coefficient less than about 0.

3. The prodrug of claim 1, where the conjugate has an octanol-water distribution coefficient greater than about 0.5.

4. The prodrug of claim 1, where the conjugate has an octanol-water distribution coefficient between about 0.5 and 3.0.

5. The prodrug of claim 1, where the diacyl carrier group has a molecular weight between about 110 and 740.

6. The prodrug of claim 1, where the diacyl carrier group comprises two oleic acid chains.

7. The prodrug of claim 1, where the parent drug is voglibose.