IP Library Granted Patent US 9,156,822
Granted Patent B2
US 9,156,822 · App. 13/807,347 · Granted Oct 13, 2015

Functionally selective ligands of dopamine D

Inventors: Jian Jin (Chapel Hill, NC); Bryan Roth (Durham, NC); Stephen Frye (Chapel Hill, NC)
Assignee: The University of North Carolina at Chapel Hill
C07D403/12A61K31/454A61K31/4725A61K31/496A61K31/4965A61K31/538A61K31/55A61K45/00C07D215/20C07D217/24C07D231/56C07D235/26C07D241/04C07D277/62C07D295/088C07D401/12C07D405/12C07D405/14C07D413/12C07D413/14C07D417/12C07D471/04
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Quick Facts
Patent No.
US 9,156,822
App. No.
13/807,347
Granted
Oct 13, 2015
Kind
B2
Abstract

The present invention relates to novel functionally selective ligands of dopamine D 2 receptors, including agonists, antagonists, and inverse agonists. The invention further relates to the use of these compounds for treating central nervous system disorders related to D 2 receptors.

Claims (28)

1. A compound of formula I:

wherein m is 1;

n is 0, 1, or 2;

q is 1 or 2;

X is O, NH, or CH 2 ;

Y is N;

Z is C, CH, CH 2 , cycloalkyl, aryl, or heteroaryl;

is a single, double, or triple bond as valencies permit;

Ar 1 is a substituted monocyclic or an unsubstituted or substituted bicyclic aryl or an unsubstituted or substituted monocyclic or bicyclic heteroaryl; and

Ar 2 is 3,4-dihydroquinolin-2(1H)-one, 3,4-dihydro-1,8-naphthyridin-2(1H)-one, quinolin-2(1H)-one, 3,4-dihydroisoquinolin-1(2H)-one, benzo[d]thiazole, 1H-benzo[d]imidazol-2(3H)-one, 1H-indazole, or benzo[d]oxazol-2(3H)-one;

or a pharmaceutically acceptable salt or optical isomer thereof.

2. The compound of claim 1 , having the structure of formula III:

wherein n is 0, 1, or 2;

X is O, NH, or CH 2 ;

Y is N;

Ar 1 is a substituted monocyclic or an unsubstituted or substituted bicyclic aryl or an unsubstituted or substituted heteroaryl; and

Ar 2 is 3,4-dihydroquinolin-2(1H)-one, 3,4-dihydro-1,8-naphthyridin-2(1H)-one, quinolin-2(1H)-one, 3,4-dihydroisoquinolin-1(2H)-one, benzo[d]thiazole, 1H-benzo[d]imidazol-2(3H)-one, 1H-indazole, or benzo[d]oxazol-2(3H)-one;

or a pharmaceutically acceptable salt or optical isomer thereof.

3. The compound of claim 1 , having the structure of formula V:

or a pharmaceutically acceptable salt or optical isomer thereof.

4. The compound of claim 1 , selected from the group consisting of:

5. The compound of claim 1 , selected from the group consisting of:

6. The compound of claim 1 , wherein n is 1.

7. The compound of claim 1 , wherein X is O.

8. The compound of claim 1 wherein Ar 2 is:

9. A pharmaceutical composition comprising the compound of claim 1 and a pharmaceutically acceptable carrier.

10. A method of treating a central nervous system disorder associated with D 2 dopamine receptors in a subject, comprising delivering to the subject a therapeutically effective amount of the compound of claim 1 , wherein the disorder associated with D 2 dopamine receptors is a disorder having a psychosis component, Parkinson's disease, pituitary adenoma, prolactinoma, or galactorrhea.

11. The method of claim 10 , wherein the disorder associated with D 2 dopamine receptors is selected from the group consisting of schizophrenia, schizoaffective disorder, schizophreniform disorder, bipolar disorder, mania, manic psychosis, Tourette's syndrome and Tourette-like disorders, obsessive-compulsive disorder, depression with psychotic features, and psychosis not otherwise specified (Psychosis NOS).

Assignments (2)
CONFIRMATORY LICENSE Recorded Jul 16, 2013
From: THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 030804/0844 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 15, 2013
From: JIN, JIAN; ROTH, BRYAN; FRYE, STEPHEN
To: THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL
Reel/Frame 029817/0047 →
Continuity (2)
Provisional Application 61360951 · Jul 2, 2010
Related Publication 20130137679A1 · May 30, 2013