IP Library Granted Patent US 9,045,428
Granted Patent B2
US 9,045,428 · App. 13/960,636 · Granted Jun 2, 2015

Substituted heterocyclic compounds

Inventors: Matthew Abelman (Mill Valley, CA); Robert H. Jiang (Cupertino, CA); Jeff Zablocki (Los Altos, CA)
Assignee: Gilead Sciences, Inc.
C07D213/80A61K31/435C07D211/90C07D215/54C07D311/74C07D311/94C07D401/04C07D405/04C07D407/04C07D409/04C07D471/04C07D487/04C07D491/147
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Quick Facts
Patent No.
US 9,045,428
App. No.
13/960,636
Granted
Jun 2, 2015
Kind
B2
Abstract

The present invention relates to novel heterocyclic compounds and to their use in the treatment of various disease states, including cardiovascular diseases and diabetes. In particular embodiments, the structure of the compounds is given by Formula (I): wherein Q1, Q2, R2, R3, R4, R5, and R6 are as described herein. The invention also relates to methods for the preparation of the compounds, and to pharmaceutical compositions containing such compounds.

Claims (28)

1. A compound selected from the group consisting of:

diethyl 4-(2,3 dihydrobenzo[b][1,4]dioxin-6-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate,

5-(3,5-bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridin-4-yl)thiophene-2-carboxylic acid,

diethyl 4-(5-ethylthiophen-2-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate,

diethyl 2,6-dimethyl-4-(3-methylbenzo[b]thiophen-2-yl)-1,4-dihydropyridine-3,5-dicarboxylate,

diethyl 2,6-dimethyl-4-(3-methylbenzo[b]thiophen-2-yl)pyridine-3,5-dicarboxylate,

diethyl 2,6-dimethyl-4-(5-(2-(trifluoromethyl)phenyl)furan-2-yl)-1,4-dihydropyridine-3,5-dicarboxylate,

diethyl 4-(furan-3-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate,

diethyl 4-(5-ethylfuran-2-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate,

diethyl 4-(benzofuran-2-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate,

diisopropyl 4-(5-bromothiophen-2-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate,

bis(2-methoxyethyl) 4-(3-bromothiophen-2-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate,

diisopropyl 4-(5-(4-chlorophenyl)furan-2-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate,

diisopropyl 4-(1-(4-fluorophenyl)-5-methyl-1H-pyrazol-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate,

diisopropyl 4-(3-(4-fluorophenyl)-1H-pyrazol-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5 dicarboxylate,

dibenzyl 2,6-dimethyl-4-(naphthalen-2-yl)-1,4-dihydropyridine-3,5-dicarboxylate,

bis(3,4-dimethoxybenzyl) 2,6-dimethyl-4-(naphthalen-2-yl)-1,4-dihydropyridine-3,5-dicarboxylate,

diethyl 4-(5-bromothiophen-2-yl)-2,6-diethyl-1,4-dihydropyridine-3,5-dicarboxylate,

diethyl 4-(5-bromothiophen-2-yl)-2,6-dipropyl-1,4-dihydropyridine-3,5-dicarboxylate,

diethyl 4-(5-bromothiophen-2-yl)-2,6-diisopropyl-1,4-dihydropyridine-3,5-dicarboxylate,

diethyl 4-(2-cyano-4-methoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate,

diethyl 4-(2-fluoro-4-methoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate,

diethyl 4-(2-methoxy-4-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate,

diethyl 4-(4-(dimethylamino)-2-methoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate,

diethyl 4-(4-(dimethylamino)-2-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate,

diethyl 4-(biphenyl-2-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, and

diethyl 4-(biphenyl-3-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, or a pharmaceutically acceptable salt thereof.

2. A pharmaceutical formulation comprising a compound according to claim 1 or a pharmaceutically acceptable salt or tautomeric form thereof, and at least one pharmaceutically acceptable excipient.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 12, 2014
From: GILEAD PALO ALTO, INC.
To: GILEAD SCIENCES, INC.
Reel/Frame 032868/0364 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 25, 2013
From: ABELMAN, MATTHEW; JIANG, ROBERT; ZABLOCKI, JEFF
To: CV THERAPEUTICS, INC.
Reel/Frame 031274/0579 →
MERGER Recorded Sep 25, 2013
From: CV THERAPEUTICS, INC.; APEX MERGER SUB, INC.
To: GILEAD PALO ALTO, INC.
Reel/Frame 031274/0619 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 25, 2013
From: GILEAD PALO ALTO, INC.
To: GILEAD SCIENCES, INC.
Reel/Frame 031274/0638 →
Continuity (4)
Continuation 12702825 · Feb 9, 2010
Continuation 12167558 · Jul 3, 2008
Provisional Application 60958632 · Jul 5, 2007
Related Publication 20130324525A1 · Dec 5, 2013