US2007259839A1PendingUtilityA1
Triterpene quaternary salts as biologically active surfactants
Est. expiryJan 18, 2022(expired)· nominal 20-yr term from priority
A61P 31/10A61P 31/04C07J 53/00C07J 63/008C07J 63/00
58
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Claims
Abstract
The invention provides novel compounds that are quaternary amine derivatives of betulin and other triterpenes. The compounds have antibacterial, antifungal, and surfactant properties.
Claims
exact text as granted — not AI-modified1 - 115 . (canceled)
116 . A compound of formula (II):
wherein,
R 1 is absent or alkylene;
R 2 is hydrogen, N + -containing heteroaryl, N + -containing heterocycle, or —N + R a R b R c ; provided at least one of R 2 , R 5 , and R 8 is N + -containing heteroaryl, N + -containing heterocycle, or —N + R a R b R c ;
R 3 is absent, or oxy;
R 4 is absent or alkylene;
R 5 is hydrogen, N + -containing heteroaryl, N + -containing heterocycle, or —N + R a R b R c ; provided at least one of R 2 , R 5 , and R 8 is N + -containing heteroaryl, N + -containing heterocycle, or —N + R a R b R c ;
R 6 is absent, oxy, thio, or imino;
R 7 is absent or alkylene;
R 8 is hydrogen, N + -containing heteroaryl, N + -containing heterocycle, or —N + R a R b R c ; provided at least one of R 2 , R 5 , and R 8 is N + -containing heteroaryl, N + -containing heterocycle, or —N + R a R b R c ;
R a , R b , and R c are each independently (C 1 -C 24 )alkyl, aryl, arylalkyl, heteroarylalkly, heterocycle, or heterocylealkyl;
any heteroaryl, heterocycle, or R a , R b , or R c of R 2 , R 5 , and R 8 can optionally be substituted on carbon with one or more alkyl, hydroxyalkyl, arylalkyl, heteroarylalkyl, aryl, heterocycle, heterocyclealkyl, oxo, hydroxy, halo, nitro, cyano, (C 1 -C 6 )alkoxy, trifluoromethyl, —COOR d , —NR d R e , or cycloalkylalkyl;
R d and R e are each independently hydrogen or alkyl;
any alkyl or alkylene of R 1 , R 2 , R 4 , R 5 , R 7 , or R 8 can be optionally substituted on carbon with one or more oxo, hydroxy, halo, nitro, cyano, (C 1 -C 6 )alkoxy, trifluoromethyl, —COOR d , or —NR d R e , and optionally interrupted on carbon with one or more oxy, imino, or thio, and is optionally partially unsaturated;
or an acceptable salt thereof.
117 . The compound of claim 116 , wherein N + -containing heteroaryl is N-pyridinium, N-methyl-2-pyridinium, N-methyl-3-pyridinium, N-methyl-4-pyridinium, N-ethyl-2-pyridinium, N-ethyl-3-pyridinium, N-ethylpyridinium, 3,5-dimethylpyridinium, or 4-(dimethylamino)pyridinium;
wherein any heteroaryl can optionally be substituted on carbon with one or more alkyl, hydroxyalkyl, arylalkyl, heteroarylalkyl, aryl, heterocycle, heterocyclealkyl, oxo, hydroxy, halo, nitro, cyano, (C 1 -C 6 )alkoxy, trifluoromethyl, —COOR d , —NR d R e , or cycloalkylalkyl; wherein R d and R e are each independently hydrogen or alkyl.
118 . The compound of claim 116 , wherein N + -containing heterocycle is N-diazabicyclo[2.2.2]octyl; N-azabicyclo[2.2.2]octyl; N-methyl-N-piperidino; N,N-dimethyl-2-piperidino; N,N-dimethyl-3-piperidino; N,N-dimethyl-4-piperidino; N-methyl-N-morpholino; N,N-dimethyl-2-morpholino; or N,N-dimethyl-3-morpholino;
wherein any heterocycle can optionally be substituted on carbon with one or more alkyl, hydroxyalkyl, arylalkyl, heteroarylalkyl, aryl, heterocycle, heterocyclealkyl, oxo, hydroxy, halo, nitro, cyano, (C 1 -C 6 )alkoxy, trifluoromethyl, —COOR d , —NR d R e , or cycloalkylalkyl; wherein R d and R e are each independently hydrogen or alkyl.
119 . The compound of claim 116 , wherein —N + —R a R b R c is N′-benzyl-N,N,N′,N′-tetramethylethylenediamine-N-yl; N,N,N′,N′-tetramethylethylenediamine-N-yl; octyldimethylammonium; tetradecyldimethylammonium; trimethylammonium; triethylammonium, or tri(hydroxymethyl)ammonium.
120 . The compound of claim 116 , wherein R 2 , R 5 , and R 8 are each independently absent, hydroxyl, N-diazabicyclo[2.2.2]octyl, N-pyridinium, N-alkyl-N-piperidino, N-alkyl-N-morpholino, N-azabicyclo[2.2.2]octyl, or —N + R a R b R c ; provided at least one of R 2 , R 5 , and R 8 is N + -containing heteroaryl, N + -containing heterocycle, or —N + R a R b R c ;
wherein N-diazabicyclo[2.2.2]octyl; N-pyridinium; N-alkyl-N-piperidino; N-alkyl-N-morpholino; and N-azabicyclo[2.2.2]octyl can optionally be substituted on one or more suitable carbon atoms with one or more oxo, hydroxy, mercapto, alkyl, hydroxyalkyl, halo, nitro, cyano, (C 1 -C 6 )alkoxy, —COOR d , or —NR d R e ; wherein any alkyl or alkylene of R 1 , R 2 , R 4 , R 5 , R 7 , or R 8 can optionally be substituted with one or more oxo or —NR d R e , and optionally interrupted with one or more oxy, imino, or thio, and can optionally be partially unsaturated; wherein R d and R e are each independently hydrogen or alkyl
121 . The compound of claim 116 , wherein R 1 is absent and R 2 is hydrogen, N-diazabicyclo[2.2.2]octyl, or N-dimethylamino-N-pyridinium.
122 . The compound of claim 116 , wherein R 3 and R 4 are absent, and R 5 is hydrogen.
123 . The compound of claim 116 , wherein R 3 is oxy; R 4 is absent or (C 1 -C 5 )alkylenecarbonyl; and R 5 is hydrogen, N-diazabicyclo[2.2.2]octyl; 4-dimethylamino-N-pyridinium; 4-hydroxybutyl-N-diazabicyclo[2.2.2]octyl; 4-benzyl-N-diazabicyclo[2.2.2]octyl; tetramethylethylenediamine-N-yl; N′-benzyl-N,N,N′,N′-tetramethylethylenediamine-N-yl; N-pyridinium; 4-hydroxymethyl-N-pyridinium; 2,4-dimethyl-N-pyridinium; 3,5-dimethyl-N-pyridinium; octyldimethylammonium; or tetradecyldimethylammonium.
124 . The compound of claim 116 , wherein R 6 is oxy; R 7 is absent or (C 1 -C 5 )alkylenecarbonyl; and R 8 is hydrogen, N-diazabicyclo[2.2.2]octyl; 4-dimethylamino-N-pyridinium; N′-(4-hydroxybutyl)-N-diazabicyclo[2.2.2]octyl; N′-benzyl-N-diazabicyclo[2.2.2]octyl; N,N,N′,N′-tetramethylethylenediamine-N-yl; N′-benzyl-N,N,N′,N′-tetramethylethylenediamine-N-yl; N-pyridinium; 4-hydroxymethyl-N-pyridinium; 2,4-dimethyl-N-pyridinium; 3,5-dimethyl-N-pyridinium; octyldimethylammonium; tetradecyldimethylammonium; 2-methyl-N-pyridinium; 4-hydroxy-N-methyl-N-piperidinium; or N-methyl-N-morpholino.
125 . The compound of claim 116 , wherein at least one of R 2 , R 5 , and R 8 is —N + R a R b R c wherein R a and R b are each independently (C 6 -C 24 )alkyl optionally substituted on carbon with one or more oxo, hydroxy, halo, cyano, (C 1 -C 6 )alkoxy, trifluoromethyl, —COOR d , or —NR d R e , and optionally interrupted on carbon with one or more oxy, imino, or thio, and optionally partially unsaturated; wherein R d and R e are each independently hydrogen or alkyl.
126 . The compound of claim 125 , wherein R 1 is absent and R 2 is hydrogen.
127 . The compound of claim 116 , wherein at least one of R 2 , R 5 , and R 8 is —N + R a R b R c wherein R a and R b are each independently (C 6 -C 24 )alkyl optionally substituted on carbon with one or more oxo, hydroxy, halo, cyano, (C 1 -C 6 )alkoxy, trifluoromethyl, —COOR d , or —NR d R e , and optionally interrupted on carbon with one or more oxy, imino, or thio, and optionally partially unsaturated; wherein R d and R e are each independently hydrogen or alkyl;
R 1 is absent and R 2 is hydrogen.
128 . The compound of claim 116 , wherein R 6 is oxy, R 7 is absent, and R 8 is hydrogen.
129 . The compound of claim 116 , wherein the R 4 is acetyl.
130 . The compound of claim 116 , wherein R 5 is —N + R a R b R c , wherein R a and R b are each (C 6 -C 24 )alkyl optionally substituted on carbon with one or more oxo, hydroxy, halo, cyano, (C 1 -C 6 )alkoxy, trifluoromethyl, —COOR d , or —NR d R e , and optionally interrupted on carbon with one or more oxy, imino, or thio, and optionally partially unsaturated;
wherein R d and R e are each independently hydrogen or alkyl.
131 . The compound of claim 116 , wherein R 5 is —N + R a R b R c wherein R a and R b are each (C 6 -C 24 )alkyl.
132 . The compound of claim 116 , wherein R 4 is —N + R a R b R c wherein R a and R b are each (C 6 -C 24 )alkyl and R d is (C 1 -C 24 )alkyl.
133 . The compound of claim 116 , wherein R 5 is —N + R a R b R d wherein R a and R b are each (C 6 -C 24 )alkyl and R c is (C 1 -C 6 )alkyl.
134 . The compound of claim 116 , wherein R 6 is absent, or oxy.
135 . The compound of claim 116 , wherein R 7 is acetyl.
136 . The compound of claim 116 , wherein R 8 is —N + R a R b R d , wherein R a and R b are each (C 6 -C 24 )alkyl optionally substituted on carbon with one or more oxo, hydroxy, halo, cyano, (C 1 -C 6 )alkoxy, trifluoromethyl, —COOR d , or —NR d R e , and optionally interrupted on carbon with one or more oxy, imino, or thio, and optionally partially unsaturated;
wherein R d and R e are each independently hydrogen or alkyl.
137 . The compound of claim 116 , wherein the R 8 is —N + R a R b R c wherein R a and R b are each (C 6 -C 24 )alkyl.
138 . The compound of claim 116 , wherein the R 8 is —N + R a R b R c wherein R a and R b are each (C 6 -C 24 )alkyl and R c is (C 1 -C 6 )alkyl.
139 . A compound of formula (II):
wherein,
R 1 is absent or alkylene;
R 2 is hydrogen, N + -containing heteroaryl, N′-containing heterocycle, or —N + R a R b R c ; provided at least one of R 2 , R 5 , and R 8 is N + -containing heteroaryl, N + -containing heterocycle, or —N + R a R b R c ;
R 3 is absent, oxy, thio, or imino;
R 4 is absent or alkylene;
R 5 is hydrogen, N + -containing heteroaryl, N + -containing heterocycle, or —N + R a R b R c ; provided at least one of R 2 , R 5 , and R 8 is N + -containing heteroaryl, N-containing heterocycle, or —N + R a R b R c ;
R 6 is absent, or oxy;
R 7 is absent or alkylene;
R 8 is hydrogen, N + -containing heteroaryl, N + -containing heterocycle, or —N + R a R b R c ; provided at least one of R 2 , R 5 , and R 8 is N + -containing heteroaryl, N + -containing heterocycle, or —N + R a R b R c ;
R a , R b , and R c are each independently (C 1 -C 24 )alkyl, aryl, arylalkyl, heteroarylalkly, heterocycle, or heterocylealkyl;
any heteroaryl, heterocycle, or R a , R b , or R c of R 2 , R 5 , and R 8 can optionally be substituted on carbon with one or more alkyl, hydroxyalkyl, arylalkyl, heteroarylalkyl, aryl, heterocycle, heterocyclealkyl, oxo, hydroxy, halo, nitro, cyano, (C 1 -C 6 )alkoxy, trifluoromethyl, —COOR d , —NR d R e , or cycloalkylalkyl;
R d and R e are each independently hydrogen or alkyl;
any alkyl or alkylene of R 1 , R 2 , R 4 , R 5 , R 7 , or R 8 can be optionally substituted on carbon with one or more oxo, hydroxy, halo, nitro, cyano, (C 1 -C 6 )alkoxy, trifluoromethyl, —COOR d , or —NR d R e , and optionally interrupted on carbon with one or more oxy, imino, or thio, and is optionally partially unsaturated;
or an acceptable salt thereof.
140 . The compound of claim 139 , wherein N + -containing heteroaryl is N-pyridinium, N-methyl-2-pyridinium, N-methyl-3-pyridinium, N-methylpyridinium, N-ethyl-2-pyridinium, N-ethyl-3-pyridinium, N-ethylpyridinium, 3,5-dimethylpyridinium, or 4-(dimethylamino)pyridinium;
wherein any heteroaryl can optionally be substituted on carbon with one or more alkyl, hydroxyalkyl, arylalkyl, heteroarylalkyl, aryl, heterocycle, heterocyclealkyl, oxo, hydroxy, halo, nitro, cyano, (C 1 -C 6 )alkoxy, trifluoromethyl, —COOR d , —N d R e , or cycloalkylalkyl; wherein R d and R e are each independently hydrogen or alkyl.
141 . The compound of claim 139 , wherein N + -containing heterocycle is N-diazabicyclo[2.2.2]octyl; N-azabicyclo[2.2.2]octyl; N-methyl-N-piperidino; N,N-dimethyl-2-piperidino; N,N-dimethyl-3-piperidino; N,N-dimethylpiperidino; N-methyl-N-morpholino; N,N-dimethyl-2-morpholino; or N,N-dimethyl-3-morpholino;
wherein any heterocycle can optionally be substituted on carbon with one or more alkyl, hydroxyalkyl, arylalkyl, heteroarylalkyl, aryl, heterocycle, heterocyclealkyl, oxo, hydroxy, halo, nitro, cyano, (C 1 -C 6 )alkoxy, trifluoromethyl, —COOR d , —NR d R e , or cycloalkylalkyl; wherein R d and R e are each independently hydrogen or alkyl.
142 . The compound of claim 139 , wherein —N + R a R b R c is N′-benzyl-N,N,N′,N′-tetramethylethylenediamine-N-yl; N,N,N′,N′-tetramethylethylenediamine-N-yl; octyldimethylammonium; tetradecyldimethylammonium; trimethylammonium; triethylammonium, or tri(hydroxymethyl)ammonium.
143 . The compound of claim 139 , wherein R 2 , R 5 , and R 8 are each independently absent, hydroxyl, N-diazabicyclo[2.2.2]octyl, N-pyridinium, N-alkyl-N-piperidino, N-alkyl-N-morpholino, N-azabicyclo[2.2.2]octyl, or —N + R a R b R c ; provided at least one of R 2 , R 5 , and R 8 is N + -containing heteroaryl, N + -containing heterocycle, or —N + R a R b R c ;
wherein N-diazabicyclo[2.2.2]octyl; N-pyridinium; N-alkyl-N-piperidino; N-alkyl-N-morpholino; and N-azabicyclo[2.2.2]octyl can optionally be substituted on one or more suitable carbon atoms with one or more oxo, hydroxy, mercapto, alkyl, hydroxyalkyl, halo, nitro, cyano, (C 1 -C 6 )alkoxy, —COOR d , or —NR d R e ; wherein any alkyl or alkylene of R 1 , R 2 , R 4 , R 5 , R 7 , or R 8 can optionally be substituted with one or more oxo or —NR d R e , and optionally interrupted with one or more oxy, imino, or thio, and can optionally be partially unsaturated; wherein R d and R e are each independently hydrogen or alkyl
144 . The compound of claim 139 , wherein R 1 is absent and R 2 is hydrogen, N-diazabicyclo[2.2.2]octyl, or N-dimethylamino-N-pyridinium.
145 . The compound of claim 139 , wherein R 3 and R 4 are absent, and R 5 is hydrogen.
146 . The compound of claim 139 , wherein R 3 is oxy; R 4 is absent or (C 1 -C 5 )alkylenecarbonyl; and R 5 is hydrogen, N-diazabicyclo[2.2.2]octyl; 4-dimethylamino-N-pyridinium; 4-hydroxybutyl-N-diazabicyclo[2.2.2]octyl; 4-benzyl-N-diazabicyclo[2.2.2]octyl; tetramethylethylenediamine-N-yl; N′-benzyl-N,N,N′,N′-tetramethylethylenediamine-N-yl; N-pyridinium; 4-hydroxymethyl-N-pyridinium; 2,4-dimethyl-N-pyridinium; 3,5-dimethyl-N-pyridinium; octyldimethylammonium; or tetradecyldimethylammonium.
147 . The compound of claim 139 , wherein R 6 is oxy; R 7 is absent or (C 1 -C 5 )alkylenecarbonyl; and R 8 is hydrogen, N-diazabicyclo[2.2.2]octyl; 4-dimethylamino-N-pyridinium; N′-(4-hydroxybutyl)-N-diazabicyclo[2.2.2]octyl; N′-benzyl-N-diazabicyclo[2.2.2]octyl; N,N,N′,N′-tetramethylethylenediamine-N-yl; N′-benzyl-N,N,N′,N′-tetramethylethylenediamine-N-yl; N-pyridinium; 4-hydroxymethyl-N-pyridinium; 2,4-dimethyl-N-pyridinium; 3,5-dimethyl-N-pyridinium; octyldimethylammonium; tetradecyldimethylammonium; 2-methyl-N-pyridinium; 4-hydroxy-N-methyl-N-piperidinium; or N-methyl-N-morpholino.
148 . The compound of claim 139 , wherein at least one of R 2 , R 5 , and R 8 is —N + R a R b R c wherein R a and R b are each independently (C 6 -C 24 )alkyl optionally substituted on carbon with one or more oxo, hydroxy, halo, cyano, (C 1 -C 6 )alkoxy, trifluoromethyl, —COOR d , or —NR d R e , and optionally interrupted on carbon with one or more oxy, imino, or thio, and optionally partially unsaturated; wherein R d and R e are each independently hydrogen or alkyl.
149 . The compound of claim 148 , wherein R 1 is absent and R 2 is hydrogen.
150 . The compound of claim 149 , wherein
R 3 is absent or oxy, R 4 is absent, R 5 is hydrogen; or R 6 is oxy, R 7 is absent, and R 8 is hydrogen.
151 . The compound of claim 139 , wherein at least one of R 2 , R 5 , and R 8 is —N + R a R b R c wherein R a and R b are each independently (C 6 -C 24 )alkyl optionally substituted on carbon with one or more oxo, hydroxy, halo, cyano, (C 1 -C 6 )alkoxy, trifluoromethyl, —COOR a , or —NR d R e , and optionally interrupted on carbon with one or more oxy, imino, or thio, and optionally partially unsaturated; wherein R d and R e are each independently hydrogen or alkyl;
R 1 is absent and R 2 is hydrogen.
152 . The compound of claim 139 , wherein the at least one of R 2 , R 5 , and R 8 is —N + R a R b R a wherein R a and R b are each independently (C 6 -C 24 )alkyl optionally substituted on carbon with one or more oxo, hydroxy, halo, cyano, (C 1 -C 6 )alkoxy, trifluoromethyl, —COOR d , or —NR d R a , and optionally interrupted on carbon with one or more oxy, imino, or thio, and optionally partially unsaturated; wherein R d and R e are each independently hydrogen or alkyl;
R 1 is absent and R 2 is hydrogen, R 3 is absent or oxy, R 4 is absent, and R 5 is hydrogen.
153 . The compound of claim 139 , wherein R 6 is oxy, R 7 is absent, and R 8 is hydrogen.
154 . The compound of claim 139 , wherein R 3 is absent, or oxy.
155 . The compound of claim 139 , wherein the R 4 is acetyl.
156 . The compound of claim 139 , wherein R 5 is —N + R a R b R c wherein R a and R b are each (C 6 -C 24 )alkyl optionally substituted on carbon with one or more oxo, hydroxy, halo, cyano, (C 1 -C 6 )alkoxy, trifluoromethyl, —COOR d , or —NR d R e , and optionally interrupted on carbon with one or more oxy, imino, or thio, and optionally partially unsaturated;
wherein R d and R e are each independently hydrogen or alkyl.
157 . The compound of claim 139 , wherein R 5 is —NR a R b R c wherein R a and R b are each (C 6 -C 24 )alkyl.
158 . The compound of claim 139 , wherein R 4 is —N + R a R b R c wherein R a and R b are each (C 6 -C 24 )alkyl and R e is (C 1 -C 24 )alkyl.
159 . The compound of claim 139 , wherein R 5 is —N + R a R b R c wherein R a and R b are each (C 6 -C 24 )alkyl and R c is (C 1 -C 6 )alkyl.
160 . The compound of claim 139 , wherein R 7 is acetyl.
161 . The compound of claim 139 , wherein R 8 is —N + R a R b R c wherein R a and R b are each (C 6 -C 24 )alkyl optionally substituted on carbon with one or more oxo, hydroxy, halo, cyano, (C 1 -C 6 )alkoxy, trifluoromethyl, —COOR d , or —NR d R e , and optionally interrupted on carbon with one or more oxy, imino, or thio, and optionally partially unsaturated;
wherein R d and R e are each independently hydrogen or alkyl.
162 . The compound of claim 139 , wherein the R 8 is —N + R a R b R c wherein R a and R b are each (C 6 -C 24 )alkyl.
163 . The compound of claim 139 , wherein the R 8 is —N + R a R b R c wherein R a and R b are each (C 6 -C 24 )alkyl and R e is (C 1 -C 6 )alkyl.
164 . A compound of formula (II):
wherein,
R 1 is absent or alkylene;
R 2 is hydrogen, N + -containing heteroaryl, N + -containing heterocycle, or —N + R a R b R c ; provided at least one of R 2 , R 5 , and R 8 is N + -containing heteroaryl, N + -containing heterocycle, or —N + R a R b R c ;
R 3 is absent, or oxy;
R 4 is absent or alkylene;
R 5 is hydrogen, N + -containing heteroaryl, N + -containing heterocycle, or —N + R a R b R c ; provided at least one of R 2 , R 5 , and R 8 is N + -containing heteroaryl, N + -containing heterocycle, or —N + R a R b R c ;
R 6 is absent, or oxy;
R 7 is absent or alkylene;
R 8 is hydrogen, N + -containing heteroaryl, N + -containing heterocycle, or —N + R a R b R c ; provided at least one of R 2 , R 5 , and R 8 is N + -containing heteroaryl, N + -containing heterocycle, or —N + R a R b R c ;
R a , R b , and R c are each independently (C 1 -C 24 )alkyl, aryl, arylalkyl, heteroarylalkly, heterocycle, or heterocylealkyl;
any heteroaryl, heterocycle, or R a , R b , or R c of R 2 , R 5 , and R 8 can optionally be substituted on carbon with one or more alkyl, hydroxyalkyl, arylalkyl, heteroarylalkyl, aryl, heterocycle, heterocyclealkyl, oxo, hydroxy, halo, nitro, cyano, (C 1 -C 6 )alkoxy, trifluoromethyl, —COOR d , —NR d R e , or cycloalkylalkyl;
R d and R e are each independently hydrogen or alkyl;
any alkyl or alkylene of R 1 , R 2 , R 4 , R 5 , R 7 , or R 8 can be optionally substituted on carbon with one or more oxo, hydroxy, halo, nitro, cyano, (C 1 -C 6 )alkoxy, trifluoromethyl, —COOR d , or —NR d R e , and optionally interrupted on carbon with one or more oxy, imino, or thio, and is optionally partially unsaturated;
or an acceptable salt thereof.
165 . The compound of claim 164 , wherein N + -containing heteroaryl is N-pyridinium, N-methyl-2-pyridinium, N-methyl-3-pyridinium, N-methyl-4-pyridinium, N-ethyl-2-pyridinium, N-ethyl-3-pyridinium, N-ethyl-4-pyridinium, 3,5-dimethylpyridinium, or 4-(dimethylamino)pyridinium;
wherein any heteroaryl can optionally be substituted on carbon with one or more alkyl, hydroxyalkyl, arylalkyl, heteroarylalkyl, aryl, heterocycle, heterocyclealkyl, oxo, hydroxy, halo, nitro, cyano, (C 1 -C 6 )alkoxy, trifluoromethyl, —COOR d , —NR d R e , or cycloalkylalkyl; wherein R d and R e are each independently hydrogen or alkyl.
166 . The compound of claim 164 , wherein N + -containing heterocycle is N-diazabicyclo[2.2.2]octyl; N-azabicyclo[2.2.2]octyl; N-methyl-N-piperidino; N,N-dimethyl-2-piperidino; N,N-dimethyl-3-piperidino; N,N-dimethylpiperidino; N-methyl-N-morpholino; N,N-dimethyl-2-morpholino; or N,N-dimethyl-3-morpholino;
wherein any heterocycle can optionally be substituted on carbon with one or more alkyl, hydroxyalkyl, arylalkyl, heteroarylalkyl, aryl, heterocycle, heterocyclealkyl, oxo, hydroxy, halo, nitro, cyano, (C 1 -C 6 )alkoxy, trifluoromethyl, —COOR d , —NR d R e , or cycloalkylalkyl; wherein R d and R e are each independently hydrogen or alkyl.
167 . The compound of claim 164 , wherein —N + —R a R b R c is N′-benzyl-N,N,N′,N′-tetramethylethylenediamine-N-yl; N,N,N′,N′-tetramethylethylenediamine-N-yl; octyldimethylammonium; tetradecyldimethylammonium; trimethylammonium; triethylammonium, or tri(hydroxymethyl)ammonium.
168 . The compound of claim 164 , wherein R 2 , R 5 , and R 8 are each independently absent, hydroxyl, N-diazabicyclo[2.2.2]octyl, N-pyridinium, N-alkyl-N-piperidino, N-alkyl-N-morpholino, N-azabicyclo[2.2.2]octyl, or —N + R a R b R c ; provided at least one of R 2 , R 5 , and R 8 is N + -containing heteroaryl, N + -containing heterocycle, or —N + R a R b R c ;
wherein N-diazabicyclo[2.2.2]octyl; N-pyridinium; N-alkyl-N-piperidino; N-alkyl-N-morpholino; and N-azabicyclo[2.2.2]octyl can optionally be substituted on one or more suitable carbon atoms with one or more oxo, hydroxy, mercapto, alkyl, hydroxyalkyl, halo, nitro, cyano, (C 1 -C 6 )alkoxy, —COOR d , or —NR d R e ; wherein any alkyl or alkylene of R 1 , R 2 , R 4 , R 5 , R 7 , or R 8 can optionally be substituted with one or more oxo or —NR d R e , and optionally interrupted with one or more oxy, imino, or thio, and can optionally be partially unsaturated; wherein R d and R e are each independently hydrogen or alkyl
169 . The compound of claim 164 , wherein R 1 is absent and R 2 is hydrogen, N-diazabicyclo[2.2.2]octyl, or N-dimethylamino-N-pyridinium.
170 . The compound of claim 164 , wherein R 3 and R 4 are absent, and R 5 is hydrogen.
171 . The compound of claim 164 , wherein R 3 is oxy; R 4 is absent or (C 1 -C 5 )alkylenecarbonyl; and R 5 is hydrogen, N-diazabicyclo[2.2.2]octyl; 4-dimethylamino-N-pyridinium; 4-hydroxybutyl-N-diazabicyclo[2.2.2]octyl; 4-benzyl-N-diazabicyclo[2.2.2]octyl; tetramethylethylenediamine-N-yl; N′-benzyl-N,N,N′,N′-tetramethylethylenediamine-N-yl; N-pyridinium; 4-hydroxymethyl-N-pyridinium; 2,4-dimethyl-N-pyridinium; 3,5-dimethyl-N-pyridinium; octyldimethylammonium; or tetradecyldimethylammonium.
172 . The compound of claim 164 , wherein R 6 is oxy; R 7 is absent or (C 1 -C 5 )alkylenecarbonyl; and R 8 is hydrogen, N-diazabicyclo[2.2.2]octyl; 4-dimethylamino-N-pyridinium; N′-(4-hydroxybutyl)-N-diazabicyclo[2.2.2]octyl; N′-benzyl-N-diazabicyclo[2.2.2]octyl; N,N,N′,N′-tetramethylethylenediamine-N-yl; N′-benzyl-N,N,N′,N′-tetramethylethylenediamine-N-yl; N-pyridinium; 4-hydroxymethyl-N-pyridinium; 2,4-dimethyl-N-pyridinium; 3,5-dimethyl-N-pyridinium; octyldimethylammonium; tetradecyldimethylammonium; 2-methyl-N-pyridinium; 4-hydroxy-N-methyl-N-piperidinium; or N-methyl-N-morpholino.
173 . The compound of claim 164 , wherein at least one of R 2 , R 5 , and R 8 is —N + R a R b R c wherein R a and R b are each independently (C 6 -C 24 )alkyl optionally substituted on carbon with one or more oxo, hydroxy, halo, cyano, (C 1 -C 6 )alkoxy, trifluoromethyl, —COOR d , or —NR d R e , and optionally interrupted on carbon with one or more oxy, imino, or thio, and optionally partially unsaturated; wherein R d and R e are each independently hydrogen or alkyl.
174 . The compound of claim 173 , wherein R 1 is absent and R 2 is hydrogen.
175 . The compound of claim 164 , wherein at least one of R 2 , R 5 , and R 8 is —N + R a R b R c wherein R a and R b are each independently (C 6 -C 24 )alkyl optionally substituted on carbon with one or more oxo, hydroxy, halo, cyano, (C 1 -C 6 )alkoxy, trifluoromethyl, —COOR d , or —NR d R e , and optionally interrupted on carbon with one or more oxy, imino, or thio, and optionally partially unsaturated; wherein R d and R e are each independently hydrogen or alkyl;
R 1 is absent and R 2 is hydrogen.
176 . The compound of claim 164 , wherein R 6 is oxy, R 7 is absent, and R 8 is hydrogen.
177 . The compound of claim 164 , wherein the R 4 is acetyl.
178 . The compound of claim 164 , wherein R 5 is —N + R a R b R c wherein R a and R b are each (C 6 -C 24 )alkyl optionally substituted on carbon with one or more oxo, hydroxy, halo, cyano, (C 1 -C 6 )alkoxy, trifluoromethyl, —COOR d , or —NR d R e , and optionally interrupted on carbon with one or more oxy, imino, or thio, and optionally partially unsaturated;
wherein R d and R e are each independently hydrogen or alkyl.
179 . The compound of claim 164 , wherein R 5 is —N + R a R b R c wherein R a and R b are each (C 6 -C 24 )alkyl.
180 . The compound of claim 164 , wherein R 4 is —N + R a R b R c wherein R a and R b are each (C 6 -C 24 )alkyl and R c is (C 1 -C 24 )alkyl.
181 . The compound of claim 164 , wherein R 5 is —N + R a R b R c wherein R a and R b are each (C 6 -C 24 )alkyl and R c is (C 1 -C 6 )alkyl.
182 . The compound of claim 164 , wherein R 7 is acetyl.
183 . The compound of claim 164 , wherein R 8 is —N + R a R b R c wherein R a and R b are each (C 6 -C 24 )alkyl optionally substituted on carbon with one or more oxo, hydroxy, halo, cyano, (C 1 -C 6 )alkoxy, trifluoromethyl, —COOR d , or —NR d R e , and optionally interrupted on carbon with one or more oxy, imino, or thio, and optionally partially unsaturated;
wherein R d and R e are each independently hydrogen or alkyl.
184 . The compound of claim 164 , wherein the R 8 is —N + R a R b R c wherein R a and R b are each (C 6 -C 24 )alkyl.
185 . The compound of claim 164 , wherein the R 8 is —N + R a R b R c wherein R a and R b are each (C 6 -C 24 )alkyl and R c is (C 1 -C 6 )alkyl.
186 . A pharmaceutical composition comprising a pharmaceutically effective diluent or carrier, and a compound of any one of claims 116 , 139 and 164 .
187 . A method of inhibiting or killing a fungus, the method comprising contacting the fungus with an effective anti-fungal amount of a compound of any one of claims 116 , 139 and 164 .
188 . A method of inhibiting or killing a bacterium, the method comprising contacting the bacterium with an effective anti-bacterial amount of a compound of any one of claims 116 , 139 and 164 .Join the waitlist — get patent alerts
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