IP Library Granted Patent US 8,962,600
Granted Patent B2
US 8,962,600 · App. 13/266,659 · Granted Feb 24, 2015

Neuroprotective compounds and their use

Inventors: Balaraman Kalyanaraman (Wauwatosa, WI); Joy Joseph (New Berlin, WI); Anumantha Kanthasamy (Ames, IA)
Assignee: The Medical College of Wisconsin, Inc.
C07C69/34C07C69/017C07F9/5407C07F9/5442
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Quick Facts
Patent No.
US 8,962,600
App. No.
13/266,659
Granted
Feb 24, 2015
Kind
B2
Abstract

Apocynin derivative compounds, active pharmaceutical ingredients, dosage forms, and methods of use thereof as neuroprotectants in the brain of mammals.

Claims (23)

1. An apocyanin derivative or apocyanin derivative dimer selected from the group consisting of:

wherein R 1 is C═O, (CH═CH) or CH 2 ,

wherein R 2 is O, NH or COO,

wherein R 3 is H, COCH 3 or CO(CH 2 ) m CH 3 ,

wherein X − is Cl − , Br − , or I − ,

wherein n is 2-16, and

wherein m is 1-16;

wherein R 1 is H, COCH 3 , or CO(CH 2 ) m CH 3 ,

wherein R 2 is O or NH,

wherein X − is Cl − , Br − , or I − ,

wherein n is 2-16, and

wherein m is 1-16;

and a prodrug, solvate or hydrate of any of structures (a)-(b).

2. A pharmaceutical dosage form comprising the apocynin derivative or apocynin derivative dimer of claim 1 and a pharmaceutically suitable carrier system.

3. The pharmaceutical dosage form of claim 2 , wherein the dosage form comprises an oral, injection, infusion, inhalation, transdermal, or implant dosage form.

4. A method of administering a therapeutically effective amount of an apocyanin derivative or apocyanin derivative dimer of claim 1 to a mammal, to obtain an increase in the amount of dopamine in the brain of the mammal or an increase in the amount of dihydroxyphenylacetic acid (DOPAC) in the mitochondria of the mammalian brain cell.

5. The method of claim 4 , wherein the apocynin derivative or apocynin derivative dimer is orally administered.

6. The apocynin derivative according to claim 1 , wherein the apocynin derivative has any one of the following structures:

or wherein the apocynin derivative is a prodrug, solvate or hydrate of any of the preceding structures.

7. The apocynin derivative of claim 1 having the structure:

wherein R 1 is H, COCH 3 , or CO(CH 2 ) m CH 3 , wherein R 2 is O or NH, wherein X − is Br − , wherein n is 2-16, and wherein m is 1-16, or a prodrug, salt, solvate or hydrate thereof.

8. The method of claim 4 , wherein the apocynin derivative further includes a pharmaceutically suitable carrier system.

9. The method of claim 8 , wherein the pharmaceutically suitable carrier system comprises an oral, injection, infusion, inhalation, transdermal, or implant dosage form.

Assignments (3)
CONFIRMATORY LICENSE Recorded Dec 6, 2018
From: MEDICAL COLLEGE OF WISCONSIN
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 047733/0484 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 13, 2012
From: KANTHASAMY, ANUMANTHA
To: IOWA STATE UNIVERSITY RESEARCH FOUNDATION, INC.
Reel/Frame 027528/0557 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 13, 2012
From: KALYANARAMAN, BALARAMAN; JOSEPH, JOY
To: MEDICAL COLLEGE OF WISCONSIN, INC.
Reel/Frame 027528/0648 →
Continuity (2)
Provisional Application 61172842 · Apr 27, 2009
Related Publication 20120108549A1 · May 3, 2012