IP Library Granted Patent US 10,806,803
Granted Patent B2
US 10,806,803 · App. 15/326,985 · Granted Oct 20, 2020

Compositions for targeting macrophages and other CD206 high expressing cells and methods of treating and diagnosis

Inventors: Larry Schlesinger (Powell, OH); Eric Bachelder (Dublin, OH); Frederick O. Cope (Dublin, OH)
Assignees: OHIO STATE INNOVATION FOUNDATION; CARDINAL HEALTH 414, LLC
A61K49/0032A61K31/4409A61K31/704A61K47/61A61K49/0054C08B37/0021
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Quick Facts
Patent No.
US 10,806,803
App. No.
15/326,985
Granted
Oct 20, 2020
Kind
B2
Abstract

Provided are compounds and compositions for targeting macrophages and other CD206 high expressing cells.

Claims (26)

1. A compound of Formula (II):

wherein

each X is independently H, L 1 -A, or L 2 -R;

each L 1 and L 2 are independently linkers;

each A independently comprises one selected from the group consisting of a therapeutic agent, a detection label, and H;

each R independently comprises one selected from the group consisting of a CD206 targeting moiety and H;

and

n is an integer greater than zero; and

wherein at least one X is L 1 -A wherein L 1 comprises a hydrazone and at least one X is L 2 -R wherein at least one L 2 comprises —(CH 2 )pS(CH 2 )qNH—, wherein p and q independently are integers from 0 to 5.

2. A compound according to claim 1 , wherein at least one R is selected from mannose, fucose, and n-acetylglucosamine.

3. A compound according to claim 1 , wherein at least one A is selected from a chemotherapeutic agent; an antibiotic; an immunological adjuvant; a compounds useful for treating tuberculosis; a steroid; a nucleotide; a peptide; a protein; microRNA; siRNA; an antiviral; an antigens; or a metal.

4. A compound according to claim 1 , wherein at least one A is a compound useful for treating tuberculosis.

5. A compound according to claim 1 , wherein at least one A is doxorubicin, isoniazid, gadolinium, gallium, silver, or a silver antibiotic.

6. A compound according to claim 1 wherein at least one L 1 is a C 2-12 hydrocarbon chain optionally interrupted by up to three heteroatoms selected from the group consisting of O, S and N.

7. A compound according to claim 1 wherein at least one L 1 comprises (CH 2 ) p S(CH 2 ) q NH, wherein p and q are integers from 0 to 5.

8. A compound according to claim 1 wherein at least one L 2 is a C 2-12 hydrocarbon chain optionally interrupted by up to three heteroatoms selected from the group consisting of O, S and N.

9. A compound according to claim 1 , wherein at least one L 1 -A comprises a chelator.

10. A compound of Formula (4):

wherein

R is mannose,

n is an integer greater than zero, and

11. A compound of Formula (7):

wherein

R is mannose,

R′ is H or CH 3 ,

n is an integer greater than zero, and

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 9, 2020
From: SCHLESINGER, LARRY
To: OHIO STATE INNOVATION FOUNDATION
Reel/Frame 053720/0247 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 1, 2020
From: THE OHIO STATE UNIVERSITY
To: OHIO STATE INNOVATION FOUNDATION
Reel/Frame 053661/0639 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 10, 2020
From: COPE, FREDERICK O.
To: NAVIDEA BIOPHARMACEUTICALS, INC.
Reel/Frame 053173/0784 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 22, 2020
From: BACHELDER, ERIC
To: OHIO STATE INNOVATION FOUNDATION
Reel/Frame 052470/0897 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 12, 2017
From: NAVIDEA BIOPHARMACEUTICALS, INC.
To: CARDINAL HEALTH 414, LLC
Reel/Frame 042680/0431 →
Continuity (5)
Provisional Application 62027733 · Jul 22, 2014
Provisional Application 62027220 · Jul 21, 2014
Provisional Application 62027193 · Jul 21, 2014
Provisional Application 62025991 · Jul 17, 2014
Related Publication 20170209584A1 · Jul 27, 2017