Lipophilic derivatives of chelate monoamides

• US 7,504,088 B2
• Filed: 06/07/2005
• Issued: 03/17/2009
• Est. Priority Date: 06/09/2004
• Status: Expired due to Fees

• Current Assignee: Kereos, Inc.
• Original Assignee: Kereos, Inc.
• Inventors: Riley, Dennis Patrick, McGhee, William D.
• Primary Examiner(s): Hartley; Michael G.
• Assistant Examiner(s): ROGERS, JAMES WILLIAM
• Application Number:
  US11/146,651
• Publication Number:
  US 20060008417A1
• Time in Patent Office: 1,379 Days
• Field of Search: 424/9.36, 424/9.363, 424/9.321, 514/124
• US Class Current: 424/9.36
• CPC Class Codes: A61K 49/085 conjugated systems
• CPC Class Codes: A61K 49/10 Organic compounds
• CPC Class Codes: A61K 49/1806 Suspensions, emulsions, colloids, dispersions
• CPC Class Codes: C07F 9/5537 the heteroring containing the structure -C(=O)-N-C(=O)- (both carbon atoms belong to the heteroring)
• CPC Class Codes: C07F 9/6524 having four or more nitrogen atoms as the only ring hetero atoms
• CPC Class Codes: C07F 9/65583 each of the hetero rings containing nitrogen as ring hetero atom

Abstract

Compounds useful for associating with nanoparticle or microparticle emulsions to obtain magnetic resonance images permit control of the relaxivity of the signal and readily associate with the particulate components. The compounds are conveniently prepared from achiral derivatives of chelating moieties.

Claims

1. A compound of the formula:

2. The compound of claim 1, wherein spacer² is CH₂CH₂.

3. The compound of claim 1, wherein spacer¹ is ethylene, tetramethylene, or hexamethylene.

4. The compound of claim 3, wherein said spacer¹ is hexamethylene.

5. The compound of claim 1, wherein Ch′

is a residue of 1,4,7,10-tetra-azacyclododecane-N,N′

,N″

,N′

″

-tetraacetic acid (DOTA) having one less carboxyl group than DOTA.

6. The compound of claim 1, wherein each R¹ is H.

7. The compound of claim 1, which further comprising a paramagnetic metal chelated to Ch′

.

8. The compound of claim 7, wherein said paramagnetic metal ion is nonradioactive.

9. The compound of claim 1, wherein said compound has the following formula

10. The compound of claim 7, wherein the paramagnetic metal ion is Gd(3+).

11. The compound of claim 10, wherein Ch′

is a residue of DOTA having one less carboxyl group than DOTA.