US 7,094,900 B2Granted

N-Aryl-2-oxazolidinones and their derivatives

AssigneePharmacia & Upjohn Company

InventorsRobert C. Gadwood, Jason M. Ochoada

Life of this patent

Estimating the term…

Abstract

The present invention provides antibacterial agents of formula I described herein.

Claims18

Dependent claims

A compound of formula I

or a pharmaceutically acceptable salt thereof wherein:
A is
X1 and Y1 together form the group —C(═O)N(R5)— wherein X1 is NR5 and Y1 is C(═O)
Z1 is
(a) NHC(═O)R1, or
(b) NHC(═S)R1;
R1 is
(a) NH2,
(b) NHC1-4alkyl,
(c) C1-4alkyl,
(d) C2-4alkenyl,
(e) —CH2C(═O)C1-4alkyl,
(f) OC1-4alkyl,
(g) SC1-4alkyl, or
(h) C3-6cycloalkyl;
Each X, Y, and Z is independently selected from
(a) H,
(b) Cl,
(c) F, or
(d) CH3
R4 is
(a) H,
(b) C1-4alkyl,
(c) OC1-4alkyl,
(d) SC1-4alkyl, or
(e) NHC1-4alkyl;
R5 is
(a) H,
(b) C1-4alkyl, or
(c) —(CH2)n—W1—(CH2)n-Z3;
W1 is
(a) —CH2—,
(b) —CH═CH—,
(c) —C≡C—, or
Z3 is
W2 is
(a) —O—,
(b) —N(R25)—, or
(c) —C(═O)—N(R25)—, wherein either the carbon or the nitrogen atom of the amide may be bound to a carbon atom of the phenyl ring of Z3;
R22 is (CH2)tNR23R24, H, halo, C1-4alkyl, —CN, —OH, —O—C1-4alkyl, —S(O)uC1-4alkyl, and —C(═O)NH2
R23 is H or C1-4 alkyl;
R24 is is H, C1-4 alkyl, —S(O)2—C1-4alkyl, —C(═O)—C1-4 alkyl, —C(═NH)—NH2, —C(═O)—C(HR26)—NR27R28;
R25 is H or C1-4 alkyl;
R26 is H, C1-4 alkyl which can be optionally substituted by —OH, —NH2, —NH—C(═NH)—NH2, —SH, —SCH3, —COOH, —C(O)NH2, and phenyl which can be optionally substituted with —OH, imidazole, indole;
R27 is H or C1-4 alkyl;
R28 is H, C1-4 alkyl, —S(O)2—C1-4alkyl, —C(═O)-C1-4 alkyl, —C(═NH)—NH2, —C(═O)—C(HR26)—NR27R27
t is 0, 1;
u is 0, 1, 2;
n is 1 or 2;
and
at each occurrence, alkyl, alkenyl, or cycloalkyl is optionally substituted with 1–3 halo, —OH, —OC1-4alkyl.

48 more elements

A compound selected from the group consisting of

N-({(5S)-3-[3-fluoro-4-(6-oxopiperidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide;
N-({(5S)-3-[3-fluoro-4-(6-oxopiperidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)propanamide;
2,2-dichloro-N-({(5S)-3-[3-fluoro-4-(6-oxopiperidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide;
2,2-difluoro-N-({(5S)-3-[3-fluoro-4-(6-oxopiperidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)ethanethioamide;
2,2-difluoro-N-({(5S)-3-[3-fluoro-4-(6-oxopiperidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide;
N-({(5S)-3-[3,5-difluoro-4-(6-oxopiperidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide;
2,2-dichloro-N-({(5S)-3-[3,5-difluoro-4-(6-oxopiperidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide;
N-({(5S)-3-[3,5-difluoro-4-(6-oxopiperidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)-2,2-difluoroethanethioamide;
N-({(5S)-3-[3,5-difluoro-4-(6-oxopiperidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)-2,2-difluoroacetamide;
N-({(5S)-2-oxo-3-[4-(6-oxopiperidin-3-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)acetamide;
N-({(5S)-2-oxo-3-[4-(6-oxopiperidin-3-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)propanamide;
2,2-dichloro-N-({(5S)-2-oxo-3-[4-(6-oxopiperidin-3-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)acetamide;
2,2-difluoro-N-({(5S)-2-oxo-3-[4-(6-oxopiperidin-3-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)ethanethioamide;
2,2-difluoro-N-({(5S)-2-oxo-3-[4-(6-oxopiperidin-3-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)ethanethioamide;
({(5S)-3-[4-(1-methyl-6-oxopiperidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide;
N-({(5S)-3-[3-fluoro-4-(2-oxopiperidin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide;
N-({(5S)-3-[3-fluoro-4-(2-oxopiperidin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)propanamide;
2,2-difluoro-N-({(5S)-3-[3-fluoro-4-(2-oxopiperidin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)ethanethioamide;
N-({(5S)-3-[3,5-difluoro-4-(2-oxopiperidin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide;
N-({(5S)-3-[3,5-difluoro-4-(2-oxopiperidin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)propanamide;
N-({(5S)-3-[3,5-difluoro-4-(2-oxopiperidin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)-2,2-difluoroethanethioamide;
N-({(5S)-2-oxo-3-[4-(2-oxopiperidin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)acetamide;
2,2-difluoro-N-({(5S)-2-oxo-3-[4-(2-oxopiperidin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)ethanethioamide;
N-({(5S)-2-oxo-3-[4-(2-oxopiperidin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)propanamide;
and
N-({(5S)-3-[4-(1-methyl-2-oxopiperidin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide.

23 more elements

Dependencies are inferred from the claim text.

Facts

Application: 10/632,742Filed 1 Aug 2003 · us provisional application
Priority: 12 Aug 2002
Published: US 2004/0072873 A115 Apr 2004
Granted: 22 Aug 2006
Term ends: Not estimatedThe source records don’t support an estimate.

Classification5 codes

C07D 405/10
Containing two hetero rings: linked by a carbon chain containing aromatic rings
A61P 31/04
Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics: antibacterial agents
C07D 413/10
Containing two hetero rings: linked by a carbon chain containing aromatic rings
C07D
Heterocyclic compounds

Family

Application60/402,783Us provisional application · filed 12 Aug 2002
US 2004/0072873 A1Pre-grant publication · published 15 Apr 2004
US 7,094,900 B2This patent

From the US filing history. Foreign family members aren’t listed.

Timeline

Citations

Open elsewhere

patentgrep

Loading patent…

Facts

Application

10/632,742Filed 1 Aug 2003 · us provisional application

Priority

12 Aug 2002

Published

US 2004/0072873 A115 Apr 2004

Granted

22 Aug 2006

Term ends

Not estimatedThe source records don’t support an estimate.

Classification5 codes

C07D 405/10
Containing two hetero rings: linked by a carbon chain containing aromatic rings
A61P 31/04
Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics: antibacterial agents
C07D 413/10
Containing two hetero rings: linked by a carbon chain containing aromatic rings
C07D
Heterocyclic compounds