IP Library Granted Patent US 9,056,855
Granted Patent B2
US 9,056,855 · App. 13/882,443 · Granted Jun 16, 2015

Metalloenzyme inhibitor compounds

Inventors: William J. Hoekstra (Durham, NC); Robert J. Schotzinger (Raleigh, NC); Stephen W. Rafferty (Durham, NC)
Assignee: Viamet Pharmaceuticals, Inc.
C07D401/06C07D409/14A61K31/505A61K31/506A61K45/06C07D239/26
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Quick Facts
Patent No.
US 9,056,855
App. No.
13/882,443
Granted
Jun 16, 2015
Kind
B2
Abstract

The instant invention describes compounds having metalloenzyme modulating activity, and methods of treating diseases, disorders or symptoms thereof mediated by such metalloenzymes.

Claims (26)

1. A compound of formula (I), or salt thereof, wherein:

R 1 is optionally substituted naphthyl, optionally substituted furanyl, optionally substituted thienyl, optionally substituted pyrrolyl, optionally substituted oxazolyl, optionally substituted oxadiazolyl, optionally substituted imidazolyl, optionally substituted thiazolyl, optionally substituted isoxazolyl, optionally substituted quinolinyl, optionally substituted pyrazolyl, optionally substituted isothiazolyl, optionally substituted pyridazinyl, optionally substituted pyrimidinyl, optionally substituted pyrazinyl, optionally substituted triazinyl, optionally substituted isoquinolinyl, or optionally substituted indazolyl;

R 2 is alkyl; and

R 3 is OH.

2. The compound of claim 1 , wherein R 1 is optionally substituted naphthyl, R 2 is alkyl, and R 3 is OH.

3. The compound of claim 2 , wherein R 1 is substituted naphthyl, R 2 is alkyl, and R 3 is OH.

4. The compound of claim 3 , wherein R 1 is naphthyl substituted with 1, 2, 3 or 4 substituents, independently selected from alkyl, alkoxy, haloalkoxy, cyano, halo, amino, mono-alkylamino, di-alkylamino, or heteroaryl.

5. A compound of formula (III), or salt thereof, wherein:

X is CH or N

R 2 is optionally substituted aryl, optionally substituted naphthyl, optionally substituted heteroaryl, optionally substituted alkyl, optionally substituted aralkyl, optionally substituted cycloalkyl, optionally substituted heterocycloalkyl, optionally substituted heteroaryl-alkyl or optionally substituted heteroaryl-(di)fluoroalkyl;

R 3 is independently H, OH, substituted alkyl, or substituted cycloalkyl; and

R 4 and R 5 are independently H, halogen, alkoxy, fluoroalkoxy containing 1-5 fluorines, cyano, carboxamido, optionally substituted aryl, or optionally substituted heteroaryl.

6. The compound of claim 5 , wherein X=CH.

7. The compound of claim 5 , wherein X=CH and R 3 is OH.

8. The compound of claim 5 , wherein X=N.

9. The compound of claim 5 that is:

1-(6,7-dimethoxynaphthalen-2-yl)-2-methyl-1-(pyrimidin-4-yl) propan-1-ol (1);

2-Methyl-1-(6-(methylthio) quinolin-2-yl)-1-(pyrimidin-4-yl) propan-1-ol (2);

1-(6-(Difluoromethoxy) quinolin-2-yl)-2-methyl-1-(pyrimidin-4-yl) propan-1-ol (3);

2-methyl-1-(pyrimidin-4-yl)-1-(6-(thiophen-2-yl)-5-(trifluoromethyl)quinolin-2-yl)propan-1-ol (4);

1-(6-chloro-5-(trifluoromethyl)quinolin-2-yl)-2-methyl-1-(pyrimidin-4-yl)propan-1-ol (5);

2-methyl-1-(pyrimidin-4-yl)-1-(6-(trifluoromethoxy)quinolin-2-yl)propan-1-ol (6);

1-(6-(difluoromethoxy)-5-(trifluoromethyl)quinolin-2-yl)-2-methyl-1-(pyrimidin-4-yl)propan-1-ol (7);

1-(6-(difluoromethoxy)-5-(thiophen-2-yl)quinolin-2-yl)-2-methyl-1-pyrimidin-4-yl)propan-1-ol (8)

or salt thereof.

10. A composition comprising a compound of claim 5 and a pharmaceutically acceptable carrier.

Assignments (5)
CHANGE OF NAME Recorded Nov 18, 2014
From: VIAMET PHARMACEUTICALS, INC.
To: INNOCRIN PHARMACEUTICALS, INC.
Reel/Frame 034282/0726 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 6, 2014
From: INNOCRIN PHARMACEUTICALS, INC.
To: VPS-1, INC.
Reel/Frame 034120/0337 →
CHANGE OF NAME Recorded Nov 6, 2014
From: VPS-1, INC.
To: VIAMET PHARMACEUTICALS, INC.
Reel/Frame 034181/0568 →
CHANGE OF NAME Recorded Nov 6, 2014
From: VIAMET PHARMACEUTICALS, INC.
To: INNOCRIN PHARMACEUTICALS, INC.
Reel/Frame 034182/0626 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 4, 2013
From: HOEKSTRA, WILLIAM J.; SCHOTZINGER, ROBERT J.; RAFFERTY, STEPHEN W.
To: VIAMET PHARMACEUTICALS, INC.
Reel/Frame 030544/0223 →
Continuity (2)
Provisional Application 61407780 · Oct 28, 2010
Related Publication 20130261135A1 · Oct 3, 2013