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US 9,248,117 B2Granted
Substituted N,N-dihaloamines as antimicrobials
AssigneeNovaBay Pharmaceuticals, Inc.
InventorsRakesh K. Jain, Timothy Shiau, Charles Francavilla, Eddy Low, Eric Douglas Turtle, Donogh John Roger O'Mahony
Life of this patent
Estimating the term…
Abstract
The present application describes compounds of Formula I: which are antimicrobial agents, including antibacterial, disinfectant, antifungal, germicidal and/or antiviral agents.
Claims7
A compound of Formula I
- or a pharmaceutically acceptable salt thereof,
- wherein
- Z is
- T1 is —Cl or —Br;
- T2 is —Cl or —Br;
- Ra and Rb are each independently H or alkyl, wherein each alkyl may be optionally substituted by alkoxy, halo or hydroxy;
- Y is —S(═O)2—, —S(═O)2CH2—, —S(═O)2NR5— or —N+(R1)(R2)—;
- W is —S(═O)2—, —S(═O)2CH2—, —S(═O)2NR5—, —N+(R1)(R2)— or absent;
- Q is —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 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49 or 50;
- V is H, acyl, alkyl, Z, or —SO3H;
- n is 1, 2 or 3;
- m, k and j are each independently 0, 1, 2 or 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 by alkoxy, halo and hydroxy;
- 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 by alkoxy, halo and hydroxy;
- each R3 is independently H, alkyl, acyl, aryl, heteroalkyl, heteroaryl, or heterocycloalkyl, each of which may be optionally substituted by alkoxy, halo and hydroxy;
- each R4 is independently H or alkyl;
- R5 is H or alkyl;
- and P is a counterion or absent, wherein the counterion is selected from the group consisting of sodium, potassium, tetramethylammonium, tetrabutylphosphonium, acetate, phosphate, sulfonate and citrate.
17 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, and
- 4-(3-(dichloroamino)-3-methylbutylsulfonyl)butane-1,2-diol.
26 more elements
Dependencies are inferred from the claim text.