# US 7,410,958 B2 · Triterpene quaternary salts as biologically active surfactants > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 7,410,958 B2 - Document ID: US7410958B2 - Status: Granted - Kind: B2 - Application number: 11/612,423 - Filed: 2006-12-18 - Published: 2007-04-19 - Granted: 2008-08-12 - Earliest claimed: 2002-01-18 - Assignees: Regents of the University of Minnesota - Inventors: Pavel A. Krasutsky; Dmytro Avilov; Tatiana Sergeeva; Dmytro A. Krasutskyy; Oksana Kolomitsyna - Web page: https://patentgrep.com/patent/US7410958B2 ## CPC - C07J 53/00: Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, {including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class} - A61P 31/04: Antibacterial agents - A61P 31/10: Antimycotics - C07J 63/00: Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms - C07J 63/008: {Expansion of ring D by one atom, e.g. D homo steroids} - C07J: STEROIDS (seco-steroids C07C) - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS ## 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 ### Claim 1 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. ### Claim 2 (depends on 1) The compound of claim 1 wherein R2, R5, and R8 are each independently hydrogen, hydroxyl, N-diazabicyclo[2.2.2]octyl, N-pyridinium, or —N+RaRbRc; provided at least one of R2, R5, and R8 is N-diazabicyclo[2.2.2]octyl, N-pyridinium, or —N+RaRbRc; wherein N-diazabicyclo[2.2.2]octyl or N-pyridinium can optionally be substituted on one or more suitable carbon atoms with one or more —NRdRe; wherein any alkyl or alkylene of R1, R2, R4, R5, R7, or R8 can be optionally substituted on carbon with one or more —NRdRe. ### Claim 3 (depends on 1) The compound of claim 1 wherein R1 is absent and R2 is hydrogen, N-diazabicyclo[2.2.2]octyl, N-pyridinium, or N-dimethylamino-N-pyridinium. ### Claim 4 (depends on 1) The compound of claim 1 wherein R3 is oxy; R4 is absent or (C1-C5)alkylenecarbonyl; and R5 is hydrogen, N-diazabicyclo[2.2.2]octyl, N-pyridinium, 4-dimethylamino-N-pyridinium, or —N+RaRbRc. ### Claim 5 (depends on 1) The compound of claim 1 wherein R6 is oxy; R7 is absent or (C1-C5)alkylenecarbonyl; and R8 is hydrogen, N-diazabicyclo[2.2.2]octyl, N-pyridinium, 4-dimethylamino-N-pyridinium, or —N+RaRbRc. ### Claim 6 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. ### Claim 7 (depends on 6) The compound of claim 6 wherein R5 is absent or oxy; R6 is absent or (C1-C5)alkylenecarbonyl; R7 is N-pyridinium or —N+RaRbRc; where N-pyridinium can optionally be substituted on carbon with one or more NRdRe; Ra, Rb, and Rc are each independently (C1-C24)alkyl; Rd and Re are each independently hydrogen or alkyl; and wherein any alkyl or alkylene of R6 or R7 can be optionally substituted on carbon with one or more NRdRe. ### Claim 8 (depends on 6) The compound of claim 6 wherein R5 is oxy. ### Claim 9 (depends on 6) The compound of claim 6 wherein R6 is acetyl. ### Claim 10 (depends on 6) The compound of claim 6 wherein R7 is N-pyridinium or —N+RaRbRc. ### Claim 11 (depends on 6) The compound of claim 6 wherein the compound is 3β-1-(N′,N′-dimethylaminopyridinium)-N-acetyloxy-19β,28-epoxy-18α-oleanan chloride, 3β-[N,N-dimethyl-N-(2-hydroxyethyl)aminoacetyloxy]-19β,28-epoxy-18α-oleanan chloride, 3β-[(N,N-dimethyl-N-octyl)aminoacetyloxy]-19β,28-epoxy-18α-oleanan chloride, 3β-[(N,N-dimethyl-N-tetradecyl)aminoacetyloxy]-19β,28-epoxy-18α-oleanan chloride, or 3β-[(N-methyl-N,N-didecyl)aminoacetyloxy]-19β,28-epoxy-18α-oleanan chloride. ### Claim 12 (depends on 1) A pharmaceutical composition comprising a compound of claim 1, and a pharmaceutically acceptable diluent or carrier. ### Claim 13 (depends on 6) A pharmaceutical composition comprising a compound of claim 6, and a pharmaceutically acceptable diluent or carrier. ### Claim 14 (depends on 1) A fungicidal composition comprising a compound of claim 1 and a fungicidal excipient. ### Claim 15 (depends on 7) A fungicidal composition comprising a compound of claim 7 and a fungicidal excipient. ### Claim 16 (depends on 1) A method of inhibiting or killing a fungus or bacterium comprising contacting the fungus or bacterium with an effective amount of a compound of claim 1, wherein the contacting is in vitro, or is on or in a plant. ### Claim 17 (depends on 16) The method of claim 16 wherein the bacterium is an antibiotic resistant bacterium. ### Claim 18 (depends on 16) The method of claim 16 wherein the fungus is growing on turf grass and the fungus causes the disease dollar spot or brown patch. ### Claim 19 (depends on 6) A method of inhibiting or killing a fungus or bacterium comprising contacting the fungus or bacterium with an effective amount of a compound of claim 6, wherein the contacting is in vitro, or is on or in a plant. ### Claim 20 (depends on 19) The method of claim 19 wherein the bacterium is an antibiotic resistant bacterium. ### Claim 21 (depends on 19) The method of claim 19 wherein the fungus is growing on turf grass and the fungus causes the disease dollar spot or brown patch.