US 2010/0137349 A1Published application

Antimicrobial oxazolidinone, hydantoin and imidazolidinone compositions

AssigneeNovaBay Pharmaceuticals, Inc.

InventorsRakesh K. Jain, Eddy Low, Charles Francavilla, Timothy P. Shiau, Bum Kim, Satheesh K. Nair

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Abstract

The present application relates to N-chlorinated oxazolidinone, hydantoin and imidazolidinone compounds of Formula I or pharmaceutically acceptable salts thereof, and associated compositions and methods of use as antimicrobial agents.

Claims21

Dependent claims

A compound of Formula I

or a salt thereof, wherein:
n is 0 or 1;
W is NR4, O, S, S(═O) or S(═O)2;
R1 is H, Cl, Br, -L-X or optionally substituted alkyl or heteroalkyl;
R2 and R3 are each independently H, -L-X or optionally substituted alkyl or heteroalkyl, or R2 and R3 together with the carbon to which they are attached form a carbonyl, -L-X or an optionally substituted cycloalkyl or heterocycloalkyl group;
R4 is H, Cl, Br, -L-X or optionally substituted alkyl or heteroalkyl;
R5 and R6 are each independently H, -L-X or optionally substituted alkyl or heteroalkyl;
or R5 and R6 together with the carbon to which they are attached form a carbonyl, -L-X, or an optionally substituted cycloalkyl or heterocycloalkyl group;
R7 and R8 are each independently H, -L-X or optionally substituted alkyl or heteroalkyl;
or R7 and R8 together with the carbon to which they are attached form a carbonyl, -L-X or an optionally substituted cycloalkyl or heterocycloalkyl group;
R9 and R10 are each independently H, -L-X or optionally substituted alkyl or heteroalkyl;
or R9 and R10 together with the carbon to which they are attached form a carbonyl, -L-X or an optionally substituted cycloalkyl or heterocycloalkyl group;
each L is independently an optionally substituted C1-6 alkyl, heteroalkyl, cycloalkyl or heterocycloalkyl group;
and
each X is independently —SO3H, —N+RaRbRc, —B(OH)2, —CO2H, —PO3H2 or —PO3HRa and Ra, Rb, and/or Rc are independently a bond or an optionally substituted alkyl or heteroalkyl groups, or may form, together with the N to which they are attached, a heterocycloalkyl group
with the provisos that:
at least one of R1, R2, R3, R4, R5, R6, R7, R8, R9 or R10 is -L-X;
and
at least one of R2 and R3, R5 and R6, or R7 and R8, together with the carbon to which they are attached, form a carbonyl;
provided that (i) R5, R6 and the carbon to which they are attached, and R7, R8 and the carbon to which they are attached, are not both carbonyl;
and (ii) R7, R8 and the carbon to which they are attached, and R9, R10 and the carbon to which they are attached, are not both carbonyl.

18 more elements

A compound selected from the group consisting of:

(3-chloro-4-methyl-2-oxooxazolidin-4-yl)methanesulfonic acid;
3-bromo-4-methyl-2-oxooxazolidin-4-yl)methanesulfonic acid;
(3-chloro-4-methyl-2-oxooxazolidin-4-yl)methanephosphonic acid;
1-(3-chloro-4-methyl-2-oxooxazolidin-4-yl)-N,N,N-trimethylmethanaminium chloride;
(3-chloro-4-ethyl-2-oxooxazolidin-4-yl)methanesulfonic acid;
(4R,5S)-(3-chloro-4,5-dimethyl-2-oxooxazolidin-4-yl)methanesulfonic acid;
(4R,5R)-(3-chloro-4,5-dimethyl-2-oxooxazolidin-4-yl)methanesulfonic acid;
(3-chloro-4,5,5-trimethyl-2-oxooxazolidin-4-yl)methanesulfonic acid;
2-(3-chloro-4-methyl-2-oxooxazolidin-4-yl)ethanesulfonic acid;
(3-chloro-4-methyl-2-oxoimidazolidin-4-yl)methanesulfonic acid;
(1-chloro-4,5,5-trimethyl-2-oxoimidazolidin-4-yl)methanesulfonic acid;
(3-chloro-2-oxooxazolidine-4,4-diyl)dimethanesulfonic acid;
(3-chloro-2-oxo-4-((trimethylammonio)methyl)oxazolidin-4-yl)methanesulfonic acid;
(3-dichloro-4-methyl-2-oxoimidazolidin-4-yl)methanesulfonic acid;
(3-bromo-1-chloro-4-methyl-2-oxoimidazolidin-4-yl)methanesulfonic acid;
(1-bromo-3-chloro-4-methyl-2-oxoimidazolidin-4-yl)methanesulfonic acid;
(3-dichloro-4-methyl-2-oxo-1,3-diazaspiro[4.4]nonan-4-yl)methanesulfonic acid;
(3-chloro-5-methyl-2-oxooxazolidin-5-yl)methanesulfonic acid;
(3-chloro-4,4,5-trimethyl-2-oxooxazolidin-5-yl)methanesulfonic acid;
(1-chloro-4-methyl-2-oxoimidazolidin-4-yl)methanesulfonic acid;
(3-chloro-1,4-dimethyl-2,5-dioxoimidazolidin-4-yl)methanesulfonic acid;
(3-dichloro-4-methyl-2,5-dioxoimidazolidin-4-yl)methanesulfonic acid;
2-(3-chloro-4,4,5,5-tetramethyl-2-oxoimidazolidin-1-yl)ethanesulfonic acid;
2-(3-chloro-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)ethanesulfonic acid;
2-(1,8-dichloro-7,7,9,9-tetramethyl-2,4-dioxo-1,3,8-triazaspiro[4.5]decan-3-yl)ethanesulfonic acid;
2-(3-chloro-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl)ethanesulfonic acid;
1-(3-chloro-1,4-dimethyl-2,5-dioxoimidazolidin-4-yl)-N,N,N-trimethylmethanaminium chloride;
2-(3-chloro-1,2,2,4-tetramethyl-5-oxoimidazolidin-4-yl)ethanesulfonic acid;
2-(1,3-dichloro-2,2,4-trimethyl-5-oxoimidazolidin-4-yl)ethanesulfonic acid;
2-(1-chloro-1,2,2,4-tetramethyl-5-oxoimidazolidin-4-yl)ethanesulfonic acid;
2-(3-chloro-2,2,4,4-tetramethyl-5-oxoimidazolidin-1-yl)ethanesulfonic acid;
2-(3-chloro-1,2,4,4-tetramethyl-5-oxoimidazolidin-2-yl)ethanesulfonic acid;
2-(1,3-dichloro-2,4,4-trimethyl-5-oxoimidazolidin-2-yl)ethanesulfonic acid;
2-(3-chloro-2,2,5,5-tetramethyl-4-oxoimidazolidin-1-yl)ethanesulfonic acid;
1-(3-chloro-2-oxooxazolidin-5-yl)-N,N,N-trimethylmethanaminium chloride;
3-chloro-8,8-dimethyl-2-oxo-1-oxa-3-aza-8-azoniaspiro[4.5]decane chloride;
1,3-dichloro-8,8-dimethyl-2,4-dioxo-1,3-diaza-8-azoniaspiro[4.5]decane;
N-((3-chloro-4-methyl-2-oxooxazolidin-4-yl)methyl)-N,N-dimethylethanaminium chloride;
2-((3-Chloro-4-methyl-2-oxooxazolidin-4-yl)methylsulfonyl)ethanesulfonic acid;
1-((3-chloro-4-methyl-2-oxooxazolidin-4-yl)methyl)-1-methylpyrrolidinium chloride;
3-(3-chloro-2,2,4,4-tetramethyl-5-oxoimidazolidin-1-yl)-N,N,N-trimethylpropan-1-aminium chloride;
3-(3-chloro-2,2,5,5-tetramethyl-4-oxoimidazolidin-1-yl)-N,N,N-trimethylpropan-1-aminium chloride;
3-(3-chloro-2,2,4,4-tetramethyl-5-oxoimidazolidin-1-yl)propane-1-sulfonic acid;
3-(3-chloro-2,2,5,5-tetramethyl-4-oxoimidazolidin-1-yl)propane-1-sulfonic acid;
2-(3-chloro-4,4-dimethyl-2-oxooxazolidin-5-ye-N,N,N-trimethylethanaminium chloride;
2-(3-chloro-4,4-dimethyl-2-oxooxazolidin-5-yl)ethanesulfonic acid;
2-(3-chloro-4,4-dimethyl-2-oxooxazolidin-5-yl)-N,N,N-trimethylethanaminium chloride;
2-(3-chloro-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl)-N,N,N-trimethylethanaminium chloride;
2-(3-Chloro-4,4-dimethyl-2-oxoimidazolidin-1-yl)-N,N,N-trimethylethanaminium acetate;
and
1-chloro-8,8-dimethyl-2-(N,N-dimethyl-piperidin-4-ium)-4-oxo-1,3-diaza-8-azoniaspiro[4.5]decane dichloride,
or a salt thereof.

49 more elements

Dependencies are inferred from the claim text.

Facts

Application: 12/612,572Filed 4 Nov 2009
Priority: 7 Nov 2008
Published: 3 Jun 2010
Term ends: Not estimatedThe source records don’t support an estimate.

Classification20 codes

A01N 43/76
Five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3: 1,3-Oxazoles; Hydrogenated 1,3-oxazoles
A01N 35/02
Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to…:…
A01N 43/90
Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds: having two or more relevant hetero rings,…
A01N 59/00
Biocides, pest repellants or attractants, or plant growth regulators containing elements or

Family

Application61/112,681Us provisional application · filed 7 Nov 2008
US 8,722,715 B2Related patent
US 2010/0137349 A1This patent

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

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Abstract

A compound of Formula I

or a salt thereof, wherein:
n is 0 or 1;
W is NR4, O, S, S(═O) or S(═O)2;
R1 is H, Cl, Br, -L-X or optionally substituted alkyl or heteroalkyl;
R2 and R3 are each independently H, -L-X or optionally substituted alkyl or heteroalkyl, or R2 and R3 together with the carbon to which they are attached form a carbonyl, -L-X or an optionally substituted cycloalkyl or heterocycloalkyl group;
R4 is H, Cl, Br, -L-X or optionally substituted alkyl or heteroalkyl;
R5 and R6 are each independently H, -L-X or optionally substituted alkyl or heteroalkyl;
or R5 and R6 together with the carbon to which they are attached form a carbonyl, -L-X, or an optionally substituted cycloalkyl or heterocycloalkyl group;
R7 and R8 are each independently H, -L-X or optionally substituted alkyl or heteroalkyl;
or R7 and R8 together with the carbon to which they are attached form a carbonyl, -L-X or an optionally substituted cycloalkyl or heterocycloalkyl group;
R9 and R10 are each independently H, -L-X or optionally substituted alkyl or heteroalkyl;
or R9 and R10 together with the carbon to which they are attached form a carbonyl, -L-X or an optionally substituted cycloalkyl or heterocycloalkyl group;
each L is independently an optionally substituted C1-6 alkyl, heteroalkyl, cycloalkyl or heterocycloalkyl group;
and
each X is independently —SO3H, —N+RaRbRc, —B(OH)2, —CO2H, —PO3H2 or —PO3HRa and Ra, Rb, and/or Rc are independently a bond or an optionally substituted alkyl or heteroalkyl groups, or may form, together with the N to which they are attached, a heterocycloalkyl group
with the provisos that:
at least one of R1, R2, R3, R4, R5, R6, R7, R8, R9 or R10 is -L-X;
and
at least one of R2 and R3, R5 and R6, or R7 and R8, together with the carbon to which they are attached, form a carbonyl;
provided that (i) R5, R6 and the carbon to which they are attached, and R7, R8 and the carbon to which they are attached, are not both carbonyl;
and (ii) R7, R8 and the carbon to which they are attached, and R9, R10 and the carbon to which they are attached, are not both carbonyl.

18 more elements

Facts

Application

12/612,572Filed 4 Nov 2009

Priority

7 Nov 2008

Published

3 Jun 2010

Term ends

Not estimatedThe source records don’t support an estimate.

Classification20 codes

A01N 43/76
Five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3: 1,3-Oxazoles; Hydrogenated 1,3-oxazoles
A01N 35/02
Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to…:…
A01N 43/90
Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds: having two or more relevant hetero rings,…
A01N 59/00
Biocides, pest repellants or attractants, or plant growth regulators containing elements or