IP Library Granted Patent US 6,897,233
Granted Patent B2
US 6,897,233 · App. 10/469,560 · Granted May 24, 2005

Peptide deformylase inhibitors

Assignee: SmithKline Beecham Corporation
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Quick Facts
Patent No.
US 6,897,233
App. No.
10/469,560
Granted
May 24, 2005
Kind
B2
Abstract

PDF inhibitors and novel methods for their use are provided.

Claims (22)

1. A compound according to formula (1):

wherein:

R1 is selected from the group consisting of C 1-6 alkyl, —C 1-2 alkylAr, and Ar;

R2 is selected from the group consisting of hydrogen, C 1-6 alkyl, —(CH 2 ) m OH, —(CH 2 ) n Ar′, —(CH 2 ) n Het, —Ar′, —SO 2 R3, —C(O)R3, —C(O)NHR3, —C(O)OR3, —CH(R4)CONR5R6, and —CH(R4)CO 2 R7;

R3 is selected from the group consisting of C 1-6 alkyl, —C 1-2 alkylAr′, and Ar′;

R4 is hydrogen, or C 1-6 alkyl;

R5 and R6 are independently selected from the group consisting of hydrogen, C 1-6 alkyl, —C 1-2 alkylAr′, and Ar′; or R5, R6 together form a five or six membered cycloalkyl ring which is optionally mono-substituted by —CH 2 OR7;

R7 is selected from the group consisting of hydrogen, and C 1-3 alkyl;

Ar is selected from the group consisting of phenyl, furyl, and thienyl, all of which may be optionally substituted by one or more Z 1 groups;

Ar′ is selected from the group consisting of phenyl, naphthyl, furyl, pyridyl, thienyl, thiazolyl, isothiazolyl, pyrazolyl, triazolyl, tetrazolyl, imidazolyl, imidazolidinyl, benzofuranyl, indolyl, thiazolidinyl, isoxazolyl, oxadiazolyl, thiadiazolyl, morpholinyl, piperidinyl, piperazinyl, pyrrolyl, and pyrimidyl, all of which may be optionally substituted by one or more Z 2 groups;

Het is selected from the group consisting of tetrahydrofuranyl and piperidinyl;

Z 1 is independently selected from the group consisting of C 1-3 alkyl, —CN, F, Cl, Br, and I;

Z 2 is independently selected from the group consisting of C 1-6 alkyl, —OR2,

—(CH 2 ) n CO 2 R4, —C(O)NR5R6, —CN, —(CH 2 ) n OH, —NO 2 , F, Cl, Br, I, —NR5R6, and —NHC(O)R1;

m is 2 to 5;

and

n is 0 to 5.

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

2-[4-Butyl-1-(5-hydroxypentyl)-2-oxopyrrolidin-3-yl]-N-hydroxyacetamide;

2-[(3R,4R)-4-Butyl-1-(5-hydroxypentyl)-2-oxopyrrolidin-3-yl]-N-hydroxyacetamide; and

2-[(3S,4S)-4-Butyl-1-(5-hydroxypentyl)-2-oxopyrrolidin-3-yl]-N-hydroxyacetamide.

3. A method of treating a bacterial infection by administering to a subject in need of treatment a compound according to claim 1 .

Assignments (2)
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 29, 2003
From: XIANG, JIA-NING; CHRISTENSEN, SIEGFRIED B. IV; LIAO, XIANGMIN; CUMMINGS, MAXWELL D.
To: SMITHKLINE BEECHAM CORPORATION
Reel/Frame 014813/0392 →
Continuity (2)
Provisional Application 6027256900 · Mar 1, 2001
Related Publication 20040077856A1 · Apr 22, 2004