IP Library Granted Patent US 7,332,485
Granted Patent B2
US 7,332,485 · App. 10/563,777 · Granted Feb 19, 2008

Peptide deformylase inhibitors

Assignee: SmithKline Beecham Corp
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Quick Facts
Patent No.
US 7,332,485
App. No.
10/563,777
Granted
Feb 19, 2008
Kind
B2
Abstract

Novel PDF inhibitors and novel methods for their use are provided.

Claims (40)

1. A compound according to Formula (1):

wherein:

A is an optionally substituted 3 to 8 membered carbocycle ring;

Y is a bond except when X is carbonyl Y is a bond or CH 2 ;

X is a carbonyl, CH 2 or a bond;

R is selected from the group consisting of aryl and heteroaryl; or a pharmaceutically acceptable salt thereof.

2. A compound according to claim 1 selected from the group consisting of:

N-Hydroxy-N-{cis-4-methyl-1-[N′-(4-trifluoromethyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cyclohexylmethyl}-formamide;

N-Hydroxy-N-{cis-4-methyl-1-[N′-(4-methyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cyclohexylmethyl}-formamide;

N-Hydroxy-N-{cis-4-methyl-1-[N′-(4-morpholin-4-yl-6-trifluoromethyl-pyrimidin-2-yl) -hydrazinocarbonyl]-cyclohexylmethyl}-formamide;

N-Hydroxy-N-{cis-4-methyl-1-[N′-(7-methyl-benzo[1,2,4]triazin-3-yl)-hydrazinocarbonyl]-cyclohexylmethyl}-formamide;

N-Hydroxy-N-{cis-4-methyl-1-[N′-(5-methyl-benzo[1,2,4]triazin-3-yl)-hydrazinocarbonyl]-cyclohexylmethyl}-formamide;

N-Hydroxy-N-{cis-4-methyl-1-[N′-(5,7-dimethyl-benzo[1,2,4]triazin-3-yl)-hydrazinocarbonyl]-cyclohexylmethyl}-formamide;

Benzofuran-2-carboxylic acid {[(cis-1-{1-](formyl-hydroxy-amino)-methyl]-4-methyl-cyclohexyl}-methanoyl)-amino]-methyl}-amide;

N-Hydroxy-N-(cis-1-{N′-[1-(7-methoxy-benzofuran-2-yl)-methanoyl]-hydrazinocarbonyl}-4-methyl-cyclohexylmethyl)-formamide;

N-Hydroxy-N-{1-[N′-(4-trifluoromethyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cyclopentylmethyl}-formamide;

N-Hydroxy-N-{1-[N′-(7-methoxy-benzofuran-2-carbonyl)-hydrazinocarbonyl]-cyclopentylmethyl}-formamide;

N-Hydroxy-N-{1-[N′-(4-trifluoromethyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cyclohexylmethyl}-formamide;

N-Hydroxy-N-{1-[N′-(7-methoxy-benzofuran-2-carbonyl)-hydrazinocarbonyl]-cyclohexylmethyl}-formamide;

N-Hydroxy-N-{1-[N′-(5-methoxy-benzo[1,2,4triazin-3-yl)-hydrazinocarbonyl]-cyclohexylmethyl}-formamide;

N-Hydroxy-N-{1-[N′-(7-methyl-benzo[1,2,4triazin-3-yl)-hydrazinocarbonyl]-cyclohexylmethyl}-formamide;

N-{4,4-Dimethyl-1-[N′-(4-trifluoromethyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cyclohexylmethyl}-N-hydroxy-formamide;

N-{4,4-Dimethyl-1-[N′-(4-methyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cyclohexylmethyl}-N-hydroxy-formamide;

N-{4,4-Dimethyl-1-[N′-(4-methyl-6-morpholin-4-yl-pyrimidin-2-yl)-hydrazinocarbonyl]-cyclohexylmethyl}-N-hydroxy-formamide;

N-{4,4-Dimethyl-1-[N′-(4-trifluoromethyl-6-morpholin-4-yl-pyrimidin-2-yl)-hydrazinocarbonyl]-cyclohexylmethyl}-N-hydroxy-formamide;

N-{4,4-Dimethyl-1-[N′-(7-methyl-benzo[1,2,4]triazin-3-yl)-hydrazinocarbonyl]-cyclohexylmethyl}-N-hydroxy-formamide;

N-{4,4-Dimethyl-1-[N′-(5-methyl-benzo[1,2,4]triazin-3-yl)-hydrazinocarbonyl]-cyclohexylmethyl}-N-hydroxy-formamide;

N-{4,4-Dimethyl-1-[N′-(4-methyl-pyridin-2-yl)-hydrazinocarbonyl]-cyclohexylmethyl}-N-hydroxy-formamide;

N-{1-[N′-(Dimethylamino-ethyl-[1,3,5]triazin-2-yl)-hydrazinocarbonyl]-4,4-dimethyl-cyclohexylmethyl}-N-hydroxy-formamide;

Benzofuran-2-carboxylic acid {[(1-{-[(formyl-hydroxy-amino)-methyl]-4,4-dimethyl-cyclohexyl}-methanoyl)-amino]-methyl}-amide;

N-Hydroxy-N-{1-[N′-(4-trifluoromethyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cycloheptylmethyl}-formamide;

N-Hydroxy-N-{1-[N′-(4-methyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cycloheptylmethyl}-formamide;

N-Hydroxy-N-{1-[N′-(4-methyl-6-morpholin-4-yl-pyrimidin-2-yl)-hydrazinocarbonyl]-cycloheptylmethyl}-formamide;

N-(1-{N′-A[4-(4-Lthyl-piperazin-1-yl)-6-methyl-pyrimidin-2-yl]-hydrazinocarbonyl}-cycloheptylmethyl)-N-hydroxy-formamide;

N-Hydroxy-N-{1-[N′-(4-methyl-pyridin-2-yl)-hydrazinocarbonyl]-cycloheptylmethyl}-formamide;

N-Hydroxy-N-{1-[N′-(5-methyl-benzo[1,2,4]triazin-3-yl)-hydrazinocarbonyl]-cycloheptylmethyl}-formamide;

N-Hydroxy-N-{1-[N′-(7-methyl-benzo[1,2,4]triazin-3-yl)-hydrazinocarbonyl]-cycloheptylmethyl}-formamide;

N-Hydroxy-N-{1-[N′-(7-methoxy-benzofuran-2-carbonyl)-hydrazinocarbonyl]-cycloheptylmethyl}-formamide; and

Benzofuran-2-carboxylic acid {[(1-{-[(formyl-hydroxy-amino)-methyl]-cycloheptyl}-methanoyl)-amino]-methyl}-amide; or a pharmaceutically acceptable salt thereof.

3. A pharmaceutical composition comprising a compound according to claim 1 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

Assignments (3)
CHANGE OF NAME Recorded Jan 8, 2010
From: SMITHKLINE BEECHAM CORPORATION
To: GLAXOSMITHKLINE LLC
Reel/Frame 023750/0387 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 17, 2006
From: GLAXO GROUP LIMITED
To: SMITHKLINE BEECHAM CORPORATION
Reel/Frame 018128/0563 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 8, 2006
From: AUBART, KELLY M.; CHRISTENSEN, IV, SIEGFRIED BENJAMIN; DURAISWAMI, CHAYA; KARPINSKI, JOSEPH M.
To: GLAXO GROUP LIMITED
Reel/Frame 018067/0194 →
Continuity (2)
Provisional Application 6048551000 · Jul 8, 2003
Related Publication 20060160802A1 · Jul 20, 2006