US 2012/0129793 A1Published application

Antimicrobial Polyether and Polyol Compounds

AssigneeNovaBay Pharmaceuticals, Inc.

InventorsRakesh K. Jain, Timothy Shiau, Charles Francavilla, Eddy Low, Eric Douglas Turtle, Donogh John Roger O'Mahony

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Abstract

The present application describes compounds of Formula I and Formula IA and as disclosed herein, that are useful as anti-microbial agents, including as antibacterial, disinfectant, antifungal, germicidal or antiviral agents.

Claims15

Dependent claims

A compound of Formula I

wherein
Z is
T1 is —Cl or —Br;
T2 is hydrogen, —Cl, —Br, alkyl, heteroalkyl, —SO2Rc, —CORc—, —C(═O)NHRc, or —C(═O)ORc;
A and B are each independently —CRaRb—, —(C═O)O—, —CH2—, —SO2— or absent;
G and E are each independently, —(C═O)—, —CRaRb—, —CH2CH2— or absent;
D is N, —N+Ra—, or —CRa—;
each Ra and Rb is independently hydrogen or optionally substituted alkyl;
Rc is an alkyl, aryl, heteroalkyl or heteroaryl;
Y and W are each independently a —O—, —SO2—, —SO2CH2—, —SO2NR5—, —N+(R1R2)—, —OC(═O)—, —NR5C(═O)—, —NR5C(═O)NR6—, —NR5C(═O)O—, —OC(═O)O—, —CF2—, —CHF—, —CH(CF3)— or absent;
Q is —CH—, —CH2— or absent;
X is —(CHR4—O)h—, —(CH2—CHR4—O)h—, —(CHOR3)h—, —(CH(CH2OR3))h—, —(CH2—CR4(OR3))h—, or a combination thereof;
h is independently an integer from about 1 to about 1000;
V is hydrogen, acyl, alkyl, Z, —SO3H, —O— or a single bond;
n is an integer from 1 to 3;
m, k and j are each independently 0 or an integer from 1 to 3;
R1 and R2 are each independently selected from the group consisting of alkyl, aryl, heteroalkyl, and heteroaryl, each of which may be optionally substituted;
or
R1 and R2 together with the nitrogen atom to which they are attached form a heterocycloalkyl group, each of which may be optionally substituted;
each R3 is independently hydrogen, alkyl, acyl, aryl, heteroalkyl, heteroaryl, or heterocycloalkyl, each of which may be optionally substituted;
each R4 is independently hydrogen or alkyl;
R5 and R6 are each independently hydrogen or alkyl;
and P is a counterion or absent;
with the provisos that (1) if Q is —CH— and V is —O— or a single bond, then V and Q are directly attached (i.e. bonded) to each other to form, together with the other groups to which they are attached, a cycloalkyl or a heterocycloalkyl, and (2) that compounds of Formula I do not include 2-(dichloroamino)-2-methylpropan-1-ol, 2-(chloroamino)-2-methylpropan-1-ol, 2-(dibromoamino)-2-methylpropan-1-ol, and 2-(bromoamino)-2-methylpropan-1-ol;
or a pharmaceutically acceptable salt thereof.

22 more elements

A compound selected from the group consisting of:

4-(2-(2-(2-methoxy)ethoxy)ethoxy)ethylsulfonyl)-N,N-dichloro-2-methylbutan-2-amine, 4-(3-(dichloroamino)-3-methylbutylsulfonyl)butane-1,2,3-triol, 3-(3-(dichloroamino)-3-methylbutylsulfonyl)propane-1,2-diol, 2-(3-(dichloroamino)-3-methylbutylsulfonyl)ethanol, 2-(2-(2-(3-(dichloroamino)-3-methylbutylsulfonyl)ethoxy)ethoxy)ethanol, 2-(2-(2-(3-(dichloroamino)-3-methylbutylsulfonyl)ethoxy)ethoxy)ethyl acetate, 3-(dichloroamino)-N-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-N,N,3-trimethylbutan-1-aminium 4-methylbenzenesulfonate, 3-(3-(dichloroamino)-3-methylbutylsulfonyl)propane-1,2-diyl diacetate, 3-(3-(dichloroamino)-3-methylbutylsulfonyl)-2-hydroxypropyl acetate, 3-(dichloroamino)-N-(2-methoxyethyl)-N,N,3-trimethylbutan-1-aminium chloride, 3-(dichloroamino)-N-(3-hydroxypropyl)-N,N,3-trimethylbutan-1-aminium chloride, N-(2-butoxyethyl)-3-(dichloroamino)-N,N,3-trimethylbutan-1-aminium chloride, 4-((1,4,7,10-tetraoxacyclododecan-2-yl)methylsulfonyl)-N,N-dichloro-2-methylbutan-2-amine, 3-(dichloroamino)-N-(2-(hexyloxy)ethyl)-N,N,3-trimethylbutan-1-aminium 4-methylbenzenesulfonate, 3-(dichloroamino)-N-(3-methoxypropyl)-N,N,3-trimethylbutan-1-aminium chloride, 3-(3-(dichloroamino)-3-methylbutylsulfonyl)butane-1,2,4-triol, N,N-Dichloro-4-(2-(2-(2-tert-butoxyethoxy)ethoxy)ethylsulfonyl)-2-methylbutan-2-amine, N,N-dichloro-4-(2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)ethylsulfonyl)-2-methylbutan-2-amine, 3-(dichloroamino)-N-(3-hydroxypropyl)-N,3-dimethylbutane-1-sulfonamide, (2S,3S,4S,5R,6S)-2-((3-(dichloroamino)-3-methylbutylsulfonyl)methyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol, N,N-dichloro-4-(2-(2-(2-ethoxyethoxy)ethoxy)ethylsulfonyl)-2-methylbutan-2-amine, N,N-dichloro-4-(2-methoxyethylsulfonyl)-2-methylbutan-2-amine, N,N-dichloro-4-(2-(2-methoxyethoxy)ethylsulfonyl)-2-methylbutan-2-amine, 3-(dichloroamino)-N-(2-hydroxyethyl)-N,3-dimethylbutane-1-sulfonamide, 8-((3-(dichloroamino)-3-methylbutyl)sulfonyl)octan-1-ol, 2-((2-(dichloroamino)-2-methylpropyl)sulfonyl)ethanol, 3-((3-(dichloroamino)-3-methylbutyl)sulfonyl)propan-1-ol, N,N-dichloro-2-methyl-4-(tetrahydrofuran-3-ylsulfonyl)butan-2-amine, 4-(3-(dichloroamino)-3-methylbutylsulfonyl)butane-1,2-diol, 1-chloro-3-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-2,2,5,5-tetramethylimidazolidin-4-one, 3-chloro-5-(hydroxymethyl)-4,4-dimethyloxazolidin-2-one, 4-chloro-1-(2-hydroxyethyl)-3,3-dimethylpiperazine-2,5-dione, 1-chloro-3-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-5,5-dimethylimidazolidine-2,4-dione, 1-chloro-3-(2-(2-(2-methoxyethoxy)ethoxy)ethylsulfonyl)ethyl)-5,5-dimethylimidazolidine-2,4-dione, 3-chloro-1-(2-(2-(2-(2-methoxyethoxy)ethoxy)ethylsulfonyl)ethyl)-4,4-dimethylimidazolidin-2-one, 4-chloro-1-(2-hydroxyethyl)-3,3,5,5-tetramethylpiperazin-2-one, 3-chloro-4-methyl-4-((2,3,4-trihydroxybutylsulfonyl)methyl)oxazolidin-2-one, 2-(3-chloro-4,4-dimethyl-2-oxoimidazolidin-1-yl)-N-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-N,N-dimethylethanaminium 4-methylbenzenesulfonate, 3,3′-(2,2′-(2,2′-oxybis(ethane-2,1-diyl)bis(oxy))bis(ethane-2,1-diyl))bis(1-chloro-2,2,5,5-tetramethylimidazolidin-4-one), 1-chloro-3-(2-(2-methoxyethoxy)ethyl)-2,2,5,5-tetramethylimidazolidin-4-one, 1-chloro-2,2,5,5-tetramethyl-3-(2,5,8,11-tetraoxamidecan-13-yl)imidazolidin-4-one, 1-chloro-3-(2-methoxyethyl)-2,2,5,5-tetramethylimidazolidin-4-one, 1-chloro-3-(3-(2-(2-methoxyethoxy)ethoxy)propyl)-2,2,5,5-tetramethylimidazolidin-4-one, 3-chloro-4-(hydroxymethyl)-1,4-dimethylimidazolidin-2-one, 1-chloro-3-(2-hydroxyethyl)imidazolidin-2-one, 1-chloro-3-(2-hydroxyethyl)-2,2,5,5-tetramethylimidazolidin-4-one, 1-chloro-3-(4-hydroxybutyl)-2,2,5,5-tetramethylimidazolidin-4-one, 1-chloro-3-(2,3-dihydroxypropyl)-2,2,5,5-tetramethylimidazolidin-4-one, 1-chloro-5-(hydroxymethyl)-5-methylpyrrolidin-2-one, 3-chloro-4-(2-(2-(methoxyethoxy)ethoxy)ethylsulfonylmethyl)-4-methyloxazolidin-2-one, 3-chloro-4,4-bis(hydroxymethyl)oxazolidin-2-one, and 7-chloro-14-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-7,14-diazadispiro[5.1.58.26]pentadecan-15-one.

Dependencies are inferred from the claim text.

Facts

Application: 13/276,145Filed 18 Oct 2011
Priority: 19 Oct 2010
Published: 24 May 2012
Term ends: Not estimatedThe source records don’t support an estimate.

Classification14 codes

A61K 31/4166
1,3-Diazoles: having oxo groups directly attached to the heterocyclic ring, e.g. phenytoin
A61P 17/00
Drugs for dermatological disorders
A61P 31/00
Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
A61P 31/02
Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics: local antiseptics

Family

Application61/394,697Us provisional application · filed 19 Oct 2010
Application61/418,334Us provisional application · filed 30 Nov 2010
US 9,248,117 B2Related patent
US 2012/0129793 A1This patent

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

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Abstract

A compound of Formula I

wherein
Z is
T1 is —Cl or —Br;
T2 is hydrogen, —Cl, —Br, alkyl, heteroalkyl, —SO2Rc, —CORc—, —C(═O)NHRc, or —C(═O)ORc;
A and B are each independently —CRaRb—, —(C═O)O—, —CH2—, —SO2— or absent;
G and E are each independently, —(C═O)—, —CRaRb—, —CH2CH2— or absent;
D is N, —N+Ra—, or —CRa—;
each Ra and Rb is independently hydrogen or optionally substituted alkyl;
Rc is an alkyl, aryl, heteroalkyl or heteroaryl;
Y and W are each independently a —O—, —SO2—, —SO2CH2—, —SO2NR5—, —N+(R1R2)—, —OC(═O)—, —NR5C(═O)—, —NR5C(═O)NR6—, —NR5C(═O)O—, —OC(═O)O—, —CF2—, —CHF—, —CH(CF3)— or absent;
Q is —CH—, —CH2— or absent;
X is —(CHR4—O)h—, —(CH2—CHR4—O)h—, —(CHOR3)h—, —(CH(CH2OR3))h—, —(CH2—CR4(OR3))h—, or a combination thereof;
h is independently an integer from about 1 to about 1000;
V is hydrogen, acyl, alkyl, Z, —SO3H, —O— or a single bond;
n is an integer from 1 to 3;
m, k and j are each independently 0 or an integer from 1 to 3;
R1 and R2 are each independently selected from the group consisting of alkyl, aryl, heteroalkyl, and heteroaryl, each of which may be optionally substituted;
or
R1 and R2 together with the nitrogen atom to which they are attached form a heterocycloalkyl group, each of which may be optionally substituted;
each R3 is independently hydrogen, alkyl, acyl, aryl, heteroalkyl, heteroaryl, or heterocycloalkyl, each of which may be optionally substituted;
each R4 is independently hydrogen or alkyl;
R5 and R6 are each independently hydrogen or alkyl;
and P is a counterion or absent;
with the provisos that (1) if Q is —CH— and V is —O— or a single bond, then V and Q are directly attached (i.e. bonded) to each other to form, together with the other groups to which they are attached, a cycloalkyl or a heterocycloalkyl, and (2) that compounds of Formula I do not include 2-(dichloroamino)-2-methylpropan-1-ol, 2-(chloroamino)-2-methylpropan-1-ol, 2-(dibromoamino)-2-methylpropan-1-ol, and 2-(bromoamino)-2-methylpropan-1-ol;
or a pharmaceutically acceptable salt thereof.

22 more elements

Facts

Application

13/276,145Filed 18 Oct 2011

Priority

19 Oct 2010

Published

24 May 2012

Term ends

Not estimatedThe source records don’t support an estimate.

Classification14 codes

A61K 31/4166
1,3-Diazoles: having oxo groups directly attached to the heterocyclic ring, e.g. phenytoin
A61P 17/00
Drugs for dermatological disorders
A61P 31/00
Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
A61P 31/02
Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics: local antiseptics