EP1539681A2 - Agents antibacteriens non halogenes et procedes permettant de produire ces agents - Google Patents

Agents antibacteriens non halogenes et procedes permettant de produire ces agents

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Publication number
EP1539681A2
EP1539681A2 EP03797920A EP03797920A EP1539681A2 EP 1539681 A2 EP1539681 A2 EP 1539681A2 EP 03797920 A EP03797920 A EP 03797920A EP 03797920 A EP03797920 A EP 03797920A EP 1539681 A2 EP1539681 A2 EP 1539681A2
Authority
EP
European Patent Office
Prior art keywords
substituted
branched
linear
unsubstituted
group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP03797920A
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German (de)
English (en)
Inventor
Gregory Scot Miracle
George Douglas Ii Hiler
David Johnathan Kitko
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Procter and Gamble Co
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Procter and Gamble Co
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Filing date
Publication date
Application filed by Procter and Gamble Co filed Critical Procter and Gamble Co
Publication of EP1539681A2 publication Critical patent/EP1539681A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
    • C07C255/60—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton at least one of the singly-bound nitrogen atoms being acylated
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen

Definitions

  • the present invention relates to non-halogenated salicylanilide antibacterial agents, more particularly nitrile-substituted salicylanilide compositions, and methods of producing 5-acyl salicylamides and using same.
  • multi-halogenated salicylanilides are effective antibacterials when used in a detergent matrix, these compounds have not enjoyed widespread use due to a variety of reasons, including but not limited to problems encountered in formulating these agents. Moreover, such halogenated salicylanilides often give rise to increased concerns regarding human and environmental safety. Applicants recognized that such drawbacks are rooted in the halogenation of salicylanilides and that, if properly synthesized and employed, non-halogenated salicylanilides can be effective antibacterials. Accordingly there remains a need for non-halogenated salicylanilides that are effective antibacterials and a means of economically synthezing and using such compounds.
  • the present invention provides antibacterial compounds, antibacterial compositions, bacteria-reducing methods, bacteria-reduced substrates/articles made by the methods that employ an antibacterial agent comprising a non-halogenated nitrile-substituted salicylanilide, and processes for producing 5-acyl salicylamides.
  • substituted means that the organic composition or radical to which the tennis applied is:
  • At least one hydrogen in the compound or radical is replaced with a moiety containing one or more (i) carbon, (ii) oxygen, (iii) sulfur, or (iv) nitrogen atoms; or
  • Moieties which may replace hydrogen as described in (b) immediately above, that contain only carbon and hydrogen atoms are hydrocarbon moieties including, but not limited to, alkyl, alkenyl, alkynyl, alkyldienyl, cycloalkyl, phenyl, alkyl phenyl, naphthyl, anthryl, phenanthryl, fluoryl, steroid groups, and combinations of these groups with each other and with polyvalent hydrocarbon groups such as alkylene, alkylidene and alkylidyne groups.
  • Moieties containing oxygen atoms that may replace hydrogen as described in (b) immediately above include, but are not limited to, hydroxy, acyl or keto, ether, epoxy, carboxy, and ester containing groups.
  • Moieties containing sulfur atoms that may replace hydrogen as described in (b) immediately above include, but are not limited to, the sulfur-containing acids and acid ester groups, thioether groups, mercapto groups and thioketo groups.
  • Moieties containing nitrogen atoms that may replace hydrogen as described in (b) immediately above include, but are not limited to, amino groups, the nitro group, azo groups, ammonium groups, amide groups, azido groups, isocyanate groups, cyano groups and nitrile groups.
  • any of the above moieties (b)(i) through (b)(iv) can be substituted into each other in either a monovalent substitution or by loss of hydrogen in a polyvalent substitution to form another monovalent moiety that can replace hydrogen in the organic compound or radical.
  • perfume means a fragrance raw material or mixture of fragrance raw materials that impart a scent, odor, essence, or fragrance characteristic.
  • fragment raw materials are compounds having a molecular weight of at least 100 g/mol and are useful in imparting an odor, fragrance, essence, or scent either alone or in combination with other "fragrance raw materials".
  • C log P of a perfume, (C log P)neig is calculated as the weighted average of the C log P values of the n individual fragrance raw materials, (C log P) , that comprise the perfume, according to the formula:
  • w is the weight of the nth fragrance raw material and wmony, the weight of the perfume, is the sum of the weights of the n individual fragrance raw materials according to the formula:
  • fragrance raw materials present in an amount such that (WJ / whyroid) > 0.01 constitute the n fragrance raw materials of the perfume for the purpose of determining (C log P) flick.
  • composition of the present invention comprises a non-halogenated nitrile-substituted salicylanilide compound of formula I.
  • R.1 for said radical is independently selected from the group consisting of: i) H; ii) Cj-Cjg linear or branched, substituted or unsubstituted alkyl; iii) C2-Cjg linear or branched, substituted or unsubstituted alkenyl; iv) C2-C16 linear or branched, substituted or unsubstituted alkynyl; v) C3-C16 linear or branched, substituted or unsubstituted cycloalkyl; vi) C3-C16 linear or branched, substituted or unsubstituted cycloalkenyl; vii) C7-C16 linear or branched,
  • (X')g-, R! for said radical may be further selected from the group consisting of CN, an amine oxide moiety, NO2 and mixtures thereof; g.) X and X', when present, are selected from O, S, and NR ⁇ ; h.) each R ⁇ is independently selected from the group consisting of: i) H; ii) C ⁇ -C j g linear or branched, substituted or unsubstituted alkyl; iii) C2-C1 g linear or branched, substituted or unsubstituted alkenyl; iv) C2-C16 linear or branched, substituted or unsubstituted alkynyl; v) C3-C16 linear or branched, substituted or unsubstituted cycloalkyl; vi) C3-C16 linear or branched, substituted or unsubstituted cycloalkenyl; vii) C -C16 linear or branched, substituted
  • the composition comprises at least one additional component selected from the group consisting of: a) a surfactant wherein either:
  • the ratio of the weight of the surfactant divided by the weight of the substituted salicylanilide compound of formula I is greater than or equal to 1.0 and further provided that the surfactant is 1 wt% or greater of the composition; or (ii) the composition comprises at least 1 wt% of a cationic surfactant, wherein the ratio of the weight of the surfactant divided by the weight of said compound I is greater than or equal to 1.0; and wherein a 10 wt% aqueous solution of this composition has a pH less than or equal to 7.0; b) from 0.5% to 90% by weight of a solvent said solvent having Hildebrand solubility parameter d ⁇ (cal/cm 3 ) 1 2 meeting the following criterion: 5 ⁇ d ⁇ ⁇ 20, wherein a 10 wt% aqueous solution of this composition has a pH ⁇ (pKa - 1) where pKa is the calculated pKa of the O-G phenol of formula I, or when G is not
  • the enzyme is selected from the group consisting of: proteases, amylases, cellulases, mannanases, xyloglucanases, pectinases, lipases, laccases, peroxidases and mixtures thereof.
  • the composition comprises at least two of said additional components.
  • the composition comprises a liquid detergent.
  • the composition comprises a compound of Formula I above wherein m is 0 or 1; t is 0 or 1; a, b and g are all 0; G is H and R 1 , when present, is not H.
  • the composition comprises a compound of Formula I above wherein m is 0 or 1; t is 0 or 1; and G is H.
  • the composition comprises a compound of Formula I above wherein m is 0 or 1; t is 0; and G is H.
  • the composition comprises a compound of Formula I above wherein m is 0 or 1; t is 0; all a, b and g are 0, and G is H.
  • the composition comprises a compound of Formula I above wherein m is 0; t is 0; all a, b and g are 0, and G is H.
  • composition comprises a compound selected from the group consisting of Formula ⁇ , Formula m or mixtures thereof:
  • R 2 for Formula II and Formula HI is selected from the group consisting of: i) H; ii) C ⁇ -C ⁇ g linear or branched, substituted or unsubstituted alkyl; iii) j-Cig linear or branched, substituted or unsubstituted alkenyl; iv) C2-C16 linear or branched, substituted or unsubstituted alkynyl; v) C3-C16 linear or branched, substituted or unsubstituted cycloalkyl; vi) C3 ⁇ C ⁇ g linear or branched, substituted or unsubstituted cycloalkenyl; vii) C7-C16 linear or branched, substituted or unsubstituted alkaryl; viii) C ⁇ -Cig linear or branched, substituted or unsubstituted aralkyl; ix) Cg-Cjg substituted or unsubstituted or unsubstit
  • R ⁇ is selected from the group consisting of C ⁇ -C ⁇ g linear or branched, substituted or unsubstituted alkyl; and Cg-C ⁇ g substituted or unsubstituted aryl.
  • Suitable surfactants for use in the compositions disclosed herein include, but are not limited to, nonionic, anionic, amphoteric, amphophilic, zwitterionic, cationic, semi-polar nonionic, and mixtures thereof.
  • Non-limiting examples of such surfactants are disclosed in U.S. Patent Nos. 3,664,961, 5,707,950 and 5,576,282.
  • said compositions comprise nonionic surfactants and/or mixtures of nonionic surfactants with other surfactants, especially anionic surfactants.
  • Suitable surfactants include, but are not limited to, linear alkylbenzene sulfonate, sodium salt (Sodium LAS), available from Huntsman Surface Sciences, 3040 Post Oak Boulevard, Houston, Texas U.S.A. 77056; Neodol 25-9 ® , available from Shell Chemical LP, PO Box 2463, Houston, Texas U.S.A. 77252; Dimethyl hydroxyethyl lauryl ammonium chloride, available from Clariant Corporation, 4331 Chesapeake Drive, Charlotte, NC U.S.A. 28216.
  • Sodium LAS linear alkylbenzene sulfonate
  • Neodol 25-9 ® available from Shell Chemical LP, PO Box 2463, Houston, Texas U.S.A. 77252
  • Dimethyl hydroxyethyl lauryl ammonium chloride available from Clariant Corporation, 4331 Chesapeake Drive, Charlotte, NC U.S.A. 28216.
  • Suitable perfumes include, but are not limited to fragrance raw materials that typically comprise alcohols, ketones, aldehydes, esters, ethers, nitriles, and cyclic and acyclic alkenes such as terpenes.
  • fragrance raw materials that are useful in the compositions of the present invention include, but are not limited to, hexyl cinnamic aldehyde; amyl cinnamic aldehyde; amyl salicylate; hexyl salicylate; terpineol; 3,7-dimethyl-cis-2,6-octadien-l-ol; 2,6- dimethyl-2-octanol; 2,6-dimethyl-7-octen-2-ol; 3,7-dimethyl-3-octanol; 3,7-dimethyl-trans-2,6- octadien-1-ol; 3,7-dimethyl-6-octen-l-ol; 3,
  • Suitable solvents for incorporation in the compositions of the present invention include propylene glycol derivatives such as n-butoxypropanol or n-butoxypropoxypropanol, water- soluble CARB ⁇ TOL® solvents or water-soluble CELLOSOLNE® solvents.
  • Water-soluble CARB ⁇ L® solvents are compounds of the 2-(2-alkoxyethoxy)ethanol class wherein the alkoxy group is derived from ethyl, propyl or butyl.
  • Water-soluble CELLOSOLNE® solvents are compounds of the 2-alkoxyethoxyethanol class, such as 2-butoxyethoxyethanol.
  • Suitable solvents include ethanolamines and alcohols such as n-butoxypropoxypropanol, butyl carbitol®, monoethanolamine (MEA), diethanolamine, triethanolamine, benzyl alcohol, methanol, ethanol, isopropyl alcohol and diols such as 2-ethyl-l,3-hexanediol and 2,2,4-trimethyl-l,3-pentanediol and mixtures thereof.
  • Suitable solvents such as CARBITOL® solvents or water-soluble CELLOSOLNE® can be obtained from The Dow Chemical Company, 40 Veronica Avenue, Somerset, New Jersey U.S.A. 08873.
  • Suitable poly(alkylene glycol) alkyl ethers for use herein include poly(propylene glycol) mono butyl ether, poly(ethylene glycol-co-propylene glycol) mono butyl ether, poly(ethylene glycol) dimethyl ether, poly(ethylene glycol-co-propylene glycol) dimethyl ether, poly(ethylene glycol) stearate or mixtures thereof.
  • Poly(propylene glycol) mono butyl ether (average molecular weight 340) is commercially available from Aldrich, P.O. Box 2060, Milwaukee, Wisconsin U.S.A. 53201.
  • Non-aqueous, low- polarity solvents such as the non-vicinal C ⁇ -Cg branched or straight chain alkylene glycols.
  • Solvents of this type include hexylene glycol (4-methyl-2,4-pentanediol), 1,6-hexanediol, 1,3- butylene glycol and 1,4-butylene glycol.
  • Other low-polarity solvent for use herein comprises the mono-, di-, tri-, or tetra- C2-C3 alkylene glycol mono C2-Cg alkyl ethers.
  • Non-limiting examples of such compounds include diethylene glycol monobutyl ether, tetraethylene glycol monobutyl ether, dipropolyene glycol monoethyl ether, and dipropylene glycol monobutyl ether.
  • Another solvent useful herein comprises the lower molecular weight polyethylene glycols (PEGs). Such materials are those having molecular weights of at least about 150 grams/mole.
  • Suitable enzymes for incorporation in the compositions of the present invention include, but are not limited to, chondriotinase, hemicellulases, endoglucanase, peroxidases, proteases, pectolyase, cellulases, xylanases, lipases, phospholipases, esterases, cutinases, isopeptidase, pectinases, pectin lyases free from other pectic enzymes, keratanases, reductases, oxidases, oxidoreductases, phenoloxidases, lipoxygenases, ligninases, pullulanases, tannases, pentosanases, malanases, ⁇ -glucanases, arabinosidases, hyaluronidase, chondroitinase, laccase, mannanases, xylanase, keratinase, polygal
  • WO 98/28400 A2 WO 98/39403 A; WO 98/06808 A; WO 98/06805 Al; WO 98/06807 Al; WO 98/39404 A; WO 98/39402 A; WO 98/16604 A; WO 98/40473 A; WO 96/16153 A; WO 96/12004 A; WO 96/16154 A; WO 96/27649 A; WO 98/03640 A; WO 98/15633 A; WO 98/06809 A; WO 98/13457 A; WO 96/28558 A; WO 98/28394 A; WO 97/09431 Al; WO 97/31090 Al; WO 97/11164; WO 99/09126; WO 98/50513; WO 99/02663; WO 98/38287 Al; WO 98/382
  • Examples of commercial ⁇ -amylases products are Purafect Ox Am® from Genencor and
  • Termamyl®, Ban®, Fungamyl® and Duramyl® all available from Novo Nordisk A/S Denmark.
  • WO 95/26397 describes other suitable amylases: ⁇ -amylases characterized by having a specific activity at least 25% higher than the specific activity of Termamyl® at a temperature range of
  • compositions of the present invention may comprise suitable adjunct ingredients including, but not limited to, builders, bleaches, bleach activators, bleach catalysts, catalytic metal complexes, enzyme stabilizing systems, chelants, optical brighteners, soil release polymers, dye transfer agents, dispersants, suds suppressors, dyes, colorants, filler salts, hydrotropes, photoactivators, fluorescers, fabric conditioners, hydrolyzable surfactants, preservatives, anti- oxidants, anti-shrinkage agents, anti-wrinkle agents, germicides, fungicides, color speckles, silvercare, anti-tarnish and/or anti-corrosion agents, alkalinity sources, solubilizing agents, carriers, processing aids, pigments and pH control agents as described in U.S.
  • suitable adjunct ingredients including, but not limited to, builders, bleaches, bleach activators, bleach catalysts, catalytic metal complexes, enzyme stabilizing systems, chelants, optical brighteners, soil release polymers, dye transfer agents
  • Patent Nos. 5,705,464, 5,710,115, 5,698,504, 5,695,679, 5,686,014 and 5,646,101 A sufficient number and amount of such adjunct ingredients may be added to form a cleaning or other consumer composition, including but not limited to, liquid detergent compositions, heavy duty detergent compositions, automatic or hand dishwashing compositions, hard surface cleaning compositions, home care compositions, fabric care compositions and dryer-added compositions.
  • compositions and compounds of the present invention can be incorporated into or include a range of different products including, but not limited to, liquid detergent compositions, heavy duty detergent compositions, automatic or hand dishwashing compositions, hard surface cleaning compositions, home care compositions, fabric care compositions and dryer-added compositions.
  • liquid detergent compositions heavy duty detergent compositions, automatic or hand dishwashing compositions, hard surface cleaning compositions, home care compositions, fabric care compositions and dryer-added compositions.
  • these products may be in any form known to those skilled in the art and the compounds and compositions of the present invetion may be incorporated into such detergents by conventional means including but not limited to simple mixing.
  • the products may be in liquid, granular, powder, tablet, paste, foam, gel, spray and bars.
  • These products may be neat or releasably absorbed or adsorbed on to a substrate, such as a woven or non-woven filament substrate.
  • bacteria When bacteria are contacted with the compositions disclosed herein and/or the compounds having Formulae I-N, for the bacteria are reduced and/or their growth is inhibited.
  • bacteria that can be reduced and/or whose growth is inhibited by contact with the compositions disclosed herein and/or the compound having Formulae I-N include, but are not limited to, Staphylococcus aureus, Staphylococcus haemolyticus, Staphylococcus capitis, Staphylococcus saprophyticus, Klebsiella pneumoniae, Proteus mirabilis, Bacillus thuringiensis; Serratia marcescens, Staphylococcus epidermidis, Salmonella typhimurium, Shigella dysenteriae, Streptococcus faecalis, Streptococcus pyogenes, Corynebacterium xerosis, Micrococcus varians, Micrococcus luteus, Peptostreptococcus anaer
  • bacteria that can be reduced and/or whose growth is inhibited by contact with the compositions disclosed herein and/or the compound having Formulae I-N include, but are not limited to, Escherichia coli, Salmonella choleraesius, Listeria monocytogenes, Staphylococcus epidermidis, Staphylococcus saprophyticus, Staphylococcus aureus, Bacillus thuringiensis, Corynebacterium xerosis and mixtures thereof.
  • bacteria that can be reduced and/or whose growth is inhibited by contact with the compositions disclosed herein and/or the compound having Formulae I-N include, but are not limited to, Staphylococcus epidermidis, Staphylococcus aureus , Staphylococcus saprophyticus, Corynebacterium xerosis, Bacillus thurengiensis and mixtures thereof.
  • Bacteria levels on a substrate can be reduced (i.e., rendered inactive, killed, etc.) and/or bacterial growth there on can be inhibited by contacting said substrate with the compositions and/or the compounds disclosed herein.
  • a bacteria-reduced or growth inhibiting substrate/article results from the practice of the method of the present invention.
  • the substrates may include food articles, such as fruits, meats and liquids, such as water.
  • the compounds of present invention include non-halogenated nitrile-substituted salicylanilide compounds having Formulae IN and N below:
  • R ⁇ for Formula IN and N is selected from the group consisting of: i) H; ii) C ⁇ -C ⁇ linear or branched, substituted or unsubstituted alkyl; iii) C2 ⁇ C ⁇ g linear or branched, substituted or unsubstituted alkenyl; iv) C2-C ⁇ linear or branched, substituted or unsubstituted alkynyl; v) Q3-CI6 linear or branched, substituted or unsubstituted cycloalkyl; vi) C3-C ⁇ g linear or branched, substituted or unsubstituted cycloalkenyl; vii) O -Ci linear or branched, substituted or unsubstituted alkaryl; viii) C7-C1 g linear or branched, substituted or unsubstituted aralkyl; ix) Cg-C ⁇ g substituted or unsubstituted aryl; and
  • G is H, a suitable charge balancing counterion (M n+ ) ⁇ y n , or a cleaveable group selected from the group consisting of Si((0)pR 3 )3, where p is independently 0 or 1; C(0)q((0)pR 3 ) r , wherein p is independently 0 or 1 and when q is 1, r is 1, and when q is
  • R 3 is independently selected from the group consisting of C j -C j i g linear or branched, substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkaryl, aralkyl, and aryl, and mixtures thereof.
  • R ⁇ for Formula IN and N is selected from the group consisting of C ⁇ -C ⁇ g linear or branched, substituted or unsubstituted alkyl and Cg-C j g substituted or unsubstituted aryl.
  • R ⁇ for Formula IN and N is selected from the group consisting of C5-C1 ⁇ linear or branched, substituted or unsubstituted alkyl and C -C ] substituted or unsubstituted aryl.
  • 5-acyl substituted salicylamides may be synthesized by obtaining a sahcylamide comprising an acyl group attached to the phenolic oxygen atom at position 2 of said salicylamide, and moving the attachment point of said acyl group from said phenolic oxygen atom to the carbon atom at the 5 position of said salicylamide as illustrated below.
  • moving said acyl group comprises the step of contacting a salicylamide comprising an acyl group attached to the phenolic oxygen atom at position 2 of said salicylamide with a Lewis acid.
  • Suitable Lewis acids include, but are not limited to aluminum chloride, stannic chloride and boron trifluoride all of which can be obtained from Aldrich, P.O. Box 2060 Milwaukee, Wisconsin U.S.A. 53201.
  • said moving step is performed in the presence of a solvent.
  • Suitable solvents include, but are not limited to carbon disulfide which can be obtained from Aldrich, P.O. Box 2060 Milwaukee, Wisconsin U.S.A. 53201.
  • the rearrangement is surprisingly found to be both chemoselective, in that the ester bond breaks in preference to the amide bond, and regioselective, in that the 5-regioisomer is obtained.
  • Any substituent that does not inhibit and/or modify the rearrangement of the acyl group may be covalently bound to the nitrogen atom of the salicylamide.
  • substituents include, but are not limited to, H, linear or branched, substituted or unsubstituted alkyl and/or substituted or unsubstituted aryl.
  • Example I A non-limiting synthesis example for making an antibacterial agent in accordance with the present invention is provided below.
  • 2-(Decanoyloxy) benzoic acid (2) is synthesized as follows: To a flame dried 250 mL three neck round bottomed flask equipped with an argon inlet, addition funnel, magnetic stir bar, and thermometer, is added 10.0 g of salicylic acid, 100 mL benzene, and 5.72 g pyridine. The addition funnel is charged, over a 60 minute period, with 13.81 g decanoyl chloride, while maintaining a temperature ⁇ 35°C. Upon complete addition, the reaction is allowed to stir for 18 hours. The reaction is then quenched with 100 mL of IN HC1 and the organic phase is then separated, dried with sodium sulfate, filtered and the filtrate evaporated to dryness. The resulting solid is dissolved in 15 mL chloroform: formic acid (97.5:2.5) and then chromatographed on silica using the chloroform: formic acid (97.5:2.5). Yield of (2) after purification is 13.8 g.
  • 2-(Decanoyloxy)-N-(4-cyanophenyl)-benzamide (4) is synthesized as follows: To a flame dried 250 mL three neck round bottomed flask, equipped with an argon inlet, magnetic stir bar, oil bath, and thermometer, is added 13.5 g of 2-(decanoyloxy) benzoic acid (2) and 100 mL toluene. The resulting solution is warmed to 90°C and 6.02 g of thionyl chloride is added, then allowed to stir for 2 hours to yield (3). Then 16.3 g of 4-cyanoanline, in 4 x 4 g portions, is added over 30 minutes. Once addition is complete the reaction is stirred for an additional 1 hour.
  • reaction is diluted with 150 mL water and then poured into a separatory funnel along with 500 mL chloroform and 250 mL IN HC1. The contents of the funnel are thoroughly mixed and allowed to separate. The aqueous phase is discarded and organic phase is washed with an additional 3 x 250 mL IN HC1. The organic phase is then dried with sodium sulfate, filtered, and the filtrate evaporated to dryness to produce the crude product as an oil. The oil can be further purified by column chromatography using 4:1 hexanes:ethyl acetate. Yield of (4) after purification is 9.6 g.
  • N-(4-Cyanophenyl)-2-hydroxy-5-(l-oxodecyl)-benzamide, (5) is synthesized as follows: To a flame dried 25 mL three neck round bottomed flask, equipped with an argon inlet, magnetic stir bar, oil bath, condenser, and thermometer, is added 1.0 g of (4) and 15 mL of carbon disulfide. To the reaction mixture is added 0.68 g of aluminum chloride and then the reaction is refluxed for 3 hours, followed by removal of the solvent. The reaction is then heated an additional 2 hours at 90°C without solvent, followed by cooling to room temperature. The residue is treated with 10 mL water and then extracted with 50 mL ethyl acetate.
  • the organic phase is separated, dried with sodium sulfate, filtered and the filtrate evaporated to yield (5).
  • the product can be further purified using column chromatography (72:25 hexanes:ethylacetate) or by crystallization from benzene. All of the aforementioned specified reagents, except (2), (3) and (4) can be obtained from Aldrich, P.O. Box 2060 Milwaukee, Wisconsin U.S.A. 53201.

Abstract

L'invention concerne des composés antibactériens, des compositions antibactériennes, des procédés permettant de réduire le taux de bactéries, des substrats/articles présentant un taux réduit de bactéries, obtenus par des procédés comprenant l'utilisation d'un agent antibactérien qui contient un salicylanilide non halogéné à substitution nitrile, ainsi que des procédés permettant de produire des 5-acyl salicylamides.
EP03797920A 2002-09-18 2003-09-18 Agents antibacteriens non halogenes et procedes permettant de produire ces agents Withdrawn EP1539681A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US41181202P 2002-09-18 2002-09-18
US411812P 2002-09-18
PCT/US2003/029837 WO2004026821A2 (fr) 2002-09-18 2003-09-18 Agents antibacteriens non halogenes et procedes permettant de produire ces agents

Publications (1)

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EP1539681A2 true EP1539681A2 (fr) 2005-06-15

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EP03797920A Withdrawn EP1539681A2 (fr) 2002-09-18 2003-09-18 Agents antibacteriens non halogenes et procedes permettant de produire ces agents

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EP (1) EP1539681A2 (fr)
JP (1) JP2006511477A (fr)
AU (1) AU2003276906A1 (fr)
MX (1) MXPA05002977A (fr)
WO (1) WO2004026821A2 (fr)

Families Citing this family (3)

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Publication number Priority date Publication date Assignee Title
WO2007104316A1 (fr) * 2006-03-16 2007-09-20 Aalborg Universitet Enrobage de matières glucidiques
RU2691100C9 (ru) 2014-09-10 2019-10-11 Басф Се Инкапсулированная очищающая композиция
KR20180117701A (ko) 2016-03-09 2018-10-29 바스프 에스이 캡슐형 세탁용 세정 조성물

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Publication number Priority date Publication date Assignee Title
MXPA03002891A (es) * 2000-10-02 2003-10-15 Univ New York State Res Found Naftilsalicilaniluros como agentes antiinflamatorios y antimicrobianos.

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2004026821A3 *

Also Published As

Publication number Publication date
AU2003276906A8 (en) 2004-04-08
WO2004026821A3 (fr) 2004-08-05
MXPA05002977A (es) 2005-06-22
AU2003276906A1 (en) 2004-04-08
WO2004026821A2 (fr) 2004-04-01
JP2006511477A (ja) 2006-04-06

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