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US 7,410,958 B2Granted
Triterpene quaternary salts as biologically active surfactants
AssigneeRegents of the University of Minnesota
InventorsPavel A. Krasutsky, Dmytro Avilov, Tatiana Sergeeva, Dmytro A. Krasutskyy, Oksana Kolomitsyna
Life of this patent
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Abstract
The invention provides novel compounds that are quaternary amine derivatives of betulin and other triterpenes. The compounds have antibacterial, antifungal, and surfactant properties.
Claims21
A compound of formula (II):
- wherein
- R1, R4, and R7 are each independently absent or (C1-C5)alkylenecarbonyl;
- R3 and R6 are each independently absent or oxy;
- R2, R5, and R8 are each independently hydrogen, hydroxyl, N+-containing heteroaryl, N+-containing heterocyclyl, or —N+RaRbRc;
- provided at least one of R2, R5, and R8 is N+-containing heteroaryl, N+-containing heterocyclyl, or N+RaRbRc;
- Ra, Rb, and Rc are each independently (C1-C24)alkyl;
- any N+-containing heteroaryl, N+-containing heterocyclyl, Ra, Rb, or Rc of R2, R5, and R8 can optionally be substituted on carbon with one or more —NRdRe;
- Rd and Re are each independently hydrogen or alkyl;
- any alkyl or alkylene of R1, R2, R4, R5, R7, or R8 can be optionally substituted on carbon with one or more —NRdRe;
- or a salt thereof.
7 more elements
A compound of formula (IV):
- wherein
- R1, R2, R3, and R4 are together —O—CH2—;
- R5 is absent or oxy;
- R6 is absent or (C1-C5)alkylenecarbonyl;
- R7 is N+-containing heteroaryl, N+-containing heterocyclyl, or —N+RaRbRc;
- Ra, Rb, and Rc are each independently (C1-C24)alkyl;
- any N+-containing heteroaryl, N+-containing heterocyclyl, or Ra, Rb, or Rc of R7 can optionally be substituted on carbon with one or more —NRdRe;
- Rd and Re are each independently hydrogen or alkyl;
- any alkyl or alkylene of R6 or R7 can be optionally substituted on carbon with one or more NRdRe;
- or a salt thereof.
7 more elements
Dependencies are inferred from the claim text.