US2007244081A1PendingUtilityA1
Triterpene quaternary salts as biologically active surfactants
Est. expiryJan 18, 2022(expired)· nominal 20-yr term from priority
A61P 31/10C07J 63/00C07J 53/00A61P 31/04C07J 63/008
56
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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 - 69 . (canceled)
70 . 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, 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.
71 . The compound of claim 70 , 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.
72 . The compound of claim 70 , 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.
73 . The compound of claim 70 , 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.
74 . The compound of claim 70 , 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
75 . The compound of claim 70 , wherein R 1 is absent and R 2 is hydrogen, N-diazabicyclo[2.2.2]octyl, or N-dimethylamino-N-pyridinium.
76 . The compound of claim 70 , wherein R 3 and R 4 are absent, and R 5 is hydrogen.
77 . The compound of claim 70 , 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.
78 . The compound of claim 70 , 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.
79 . The compound of claim 70 , 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.
80 . The compound of claim 79 , wherein R 1 is absent and R 2 is hydrogen.
81 . The compound of claim 80 , 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.
82 . The compound of claim 70 , 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.
83 . The compound of claim 70 , wherein the 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, R 3 is absent or oxy, R 4 is absent, and R 5 is hydrogen.
84 . The compound of claim 70 , wherein R 6 is oxy, R 7 is absent, and R 8 is hydrogen.
85 . The compound of claim 70 , wherein R 3 is absent, or oxy.
86 . The compound of claim 70 , wherein the R 4 is acetyl.
87 . The compound of claim 70 , 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.
88 . The compound of claim 70 , wherein R 5 is —N + R a R b R c wherein R a and R b are each (C 6 -C 24 )alkyl.
89 . The compound of claim 70 , 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.
90 . The compound of claim 70 , 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.
91 . The compound of claim 70 , wherein R 6 is absent, or oxy.
92 . The compound of claim 70 , wherein R 7 is acetyl.
93 . The compound of claim 70 , 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.
94 . The compound of claim 70 , 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.
95 . The compound of claim 70 , 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.
96 . A pharmaceutical composition comprising a pharmaceutically effective diluent or carrier, and 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, 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;
wherein R d and R e are each independently hydrogen or alkyl;
wherein 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.
97 . A method of killing or inhibiting a bacterium, the method comprising contacting the bacterium with an effective anti-bacterial amount of 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, 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.
98 . The method of claim 97 , wherein the bacterium is antibiotic resistant.
99 . A compound of formula (IV)
wherein
R 1 , R 2 , R 3 and R 4 are together —O—C(═X)—; wherein X is two hydrogens, oxo, or thioxo (═S);
R 5 is absent, oxy, thio, or imino;
R 6 is absent or alkylene;
R 7 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, heteroarylalkyl, heterocycle, or heterocylealkyl;
any heteroaryl, heterocycle, or R a , R b , or R c of R 4 and R 7 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;
any cycloalkylalkyl can optionally be substituted on carbon with one or more hydroxyl, N + -containing heteroaryl, N + -containing heterocycle, —N + R a R b R c , N + -containing heteroarylalkyloxy, N + -containing heterocyclealkyloxy, or —N + R a R b R c oxy;
R d and R e are each independently hydrogen or alkyl;
any alkyl or alkylene of R 3 , R 4 , R 6 , or R 7 can be optionally substituted on carbon with one or more oxo, hydroxy, halo, aryl, 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.
100 . The compound of claim 99 , wherein R 1 , R 2 , R 3 , and R 4 are together —O—CH 2 —.
101 . The compound of claim 99 , wherein R 5 is oxy.
102 . The compound of claim 99 , wherein R 6 is acetyl.
103 . The compound of claim 99 , wherein R 7 is N-diazabicyclo[2.2.2]octyl; N-pyridinium; or —N + (CH 3 ) 3 .
104 . The compound of claim 103 , wherein
R 5 is oxy, thio, or imino; R 6 is alkylene optionally substituted on carbon with one or more oxo, hydroxy, halo, cyano, (C 1 -C 6 )alkoxy, trifluoromethyl, or —NR d R e , and optionally interrupted on carbon with one or more oxy, imino, or thio, and is optionally partially unsaturated; and R 7 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.
105 . The compound of claim 99 , 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-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.
106 . The compound of claim 99 , 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.
107 . The compound of claim 99 , 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.
108 . The compound of claim 99 , wherein R 6 is alkylene optionally substituted with one or more oxo
109 . The compound of claim 99 , wherein R 7 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.
110 . The compound of claim 99 , wherein R 7 is —N + —R a R b R c wherein R a and R b are each (C 6 -C 24 )alkyl.
111 . The compound of claim 99 , wherein R 7 is —N + —R a R b R c , wherein R a and R b are each (C 6 -C 24 )alkyl and R a is (C 6 -C 24 )alkyl.
112 . The compound of claim 99 , wherein R 7 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 6 -C 24 )alkyl.
113 . A pharmaceutical composition comprising a pharmaceutically effective diluent or carrier, and a compound of formula (IV)
wherein
R 1 , R 2 , R 3 and R 4 are together O—C(═X); wherein X is two hydrogens, oxo, or thioxo (═S);
R 5 is absent, oxy, thio, or imino;
R 6 is absent or alkylene;
R 7 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, heteroarylalkyl, heterocycle, or heterocylealkyl;
any heteroaryl, heterocycle, or R a , R b , or R c of R 4 and R 7 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;
any cycloalkylalkyl can optionally be substituted on carbon with one or more hydroxyl, N + -containing heteroaryl, N + -containing heterocycle, —N + R a R b R c , N + -containing heteroarylalkyloxy, N + -containing heterocyclealkyloxy, or —N + R a R b R c oxy;
R d and R e are each independently hydrogen or alkyl;
any alkyl or alkylene of R 3 , R 4 , R 6 , or R 7 can be optionally substituted on carbon with one or more oxo, hydroxy, halo, aryl, 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.
114 . A method of killing or inhibiting a bacterium, the method comprising contacting the bacterium with an effective anti-bacterial amount of a compound of formula (IV)
wherein
R 1 , R 2 , R 3 and R 4 are together O—C(═X); wherein X is two hydrogens, oxo, or thioxo (═S);
R 5 is absent, oxy, thio, or imino;
R 6 is absent or alkylene;
R 7 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, heteroarylalkyl, heterocycle, or heterocylealkyl;
any heteroaryl, heterocycle, or R a , R b , or R c of R 4 and R 7 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;
any cycloalkylalkyl can optionally be substituted on carbon with one or more hydroxyl, N + -containing heteroaryl, N + -containing heterocycle, —N + R a R b R c , N + -containing heteroarylalkyloxy, N + -containing heterocyclealkyloxy, or —N + R a R b R c oxy;
R d and R e are each independently hydrogen or alkyl;
any alkyl or alkylene of R 3 , R 4 , R 6 , or R 7 can be optionally substituted on carbon with one or more oxo, hydroxy, halo, aryl, 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.
115 . The method of claim 114 , wherein the bacterium is antibiotic resistant.Join the waitlist — get patent alerts
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