+

WO1998034943A1 - Amines et glycosides tensio-actifs - Google Patents

Amines et glycosides tensio-actifs Download PDF

Info

Publication number
WO1998034943A1
WO1998034943A1 PCT/NL1998/000077 NL9800077W WO9834943A1 WO 1998034943 A1 WO1998034943 A1 WO 1998034943A1 NL 9800077 W NL9800077 W NL 9800077W WO 9834943 A1 WO9834943 A1 WO 9834943A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
alkyl
chor
represent
formula
Prior art date
Application number
PCT/NL1998/000077
Other languages
English (en)
Inventor
Piet Marc Paul Bogaert
Patrick Simon Georges Tassignon
Theodoor Maximiliaan Slaghek
Original Assignee
Instituut Voor Agrotechnilogisch Onderzoek (Ato-Dlo)
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Instituut Voor Agrotechnilogisch Onderzoek (Ato-Dlo) filed Critical Instituut Voor Agrotechnilogisch Onderzoek (Ato-Dlo)
Publication of WO1998034943A1 publication Critical patent/WO1998034943A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/56—Glucosides; Mucilage; Saponins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • C07H15/10—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical containing unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
    • C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C07C229/12—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of acyclic carbon skeletons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/89—Carboxylic acid amides having nitrogen atoms of carboxamide groups quaternised
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
    • C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/18—Quaternary ammonium compounds

Definitions

  • the invention relates to novel surface-active secondary amine compounds and glycosides.
  • GB 2237018 discloses the use of methyl 12- and 9-aminooctadecanoate as components of pharmaceutical compositions which modify the lipid structure of cell membranes.
  • US patents 2,312,967 and 2,610,212 describe the preparation of 12-amino- octadecanoic acid by reductive amination of 12-oxo-octadecanoic acid.
  • Alkyl glycosides having a long aliphatic chain are known from Biermann et al, Starch/St ⁇ rke, 45 (1993) 281-288, Balzer, Tenside Surf. Det. 28 (1991) 419-427, and others. It has been found now that polar derivatives of certain secondary aminoalkyl compounds, as well as certain alkyl glycosides, have a more useful combination of surfactant properties and critical micelle concentration.
  • novel secondary amine surfactant derivatives comply with formula 1
  • A represents a C ⁇ -C ⁇ alkylene group, in particular a decamethylene group
  • R 1 represents hydroxymethyl, carbamoyl, carboxyl or C ⁇ -C alkoxycarbonyl
  • R represents a C 5 -C 9 alkyl group, in particular a hexyl group
  • R and R each represent hydrogen or a C j - t alkyl group, in particular a methyl group, or R 10 and R 11 together with the nitrogen atom represent a pyrrolidino, piperidino or morpholino group; R can also be absent (neutral amine);
  • R represents a C ⁇ - 2Q alkyl, alkenyl, alkynyl, cycloalkyl(alkyl), aralkyl or acyl group, which group may be interrupted by one or more oxygen atoms or imino groups, or a
  • R 12 may also represent a group having the formula Sac-(Z-A )n-, wherein
  • A represents a C 2 -C 6 alkylene group optionally substituted by hydroxy
  • Z represents an oxygen atom or an imino group optionally substituted by a alkyl, hydroxyalkyl or acyl group; n is an integer of 0-4; and
  • Sac represents a sugar residue
  • These compounds can be cationic and anionic as well as non-ionic or zwitterionic.
  • these surface-active amine compounds are 9- and 12-trimethyl- ammonio-, -benzyldimethylammonio-, -(carboxymethyl)dimethylammonio-, -(3- sulphopropyl)dimethylammonio-, -acetyldimethylammonio-, -phosphomethylamino- and - ⁇ -sulphosuccinoylamino-stearic acid and esters thereof, as well as analogues wherein one or more ethyleneimino groups are bound to the amine nitrogen, such as in
  • the sugar residue represented by Sac has the formula:
  • R 3 , R 4 , R and R each represent hydrogen, a C j -C ⁇ alkyl, alkenyl, aralkyl or acyl group or a C j -03 alkyl or C 2 -C alkanoyl group substituted by a carboxyl, phospho and/or sulpho group;
  • R 7 represents hydrogen, a carboxyl group or a group CH 2 OR ;
  • R 8 represents hydrogen or together with one of the symbols R and R 6 forms a direct bond; wherein one of the symbols R 3 , R 4 , R 5 and R may also represent a sugar residue [R 6 OCHR 7 -CHOR 5 -CHOR 4 -CHOR 3 -CHR 8 -].
  • glycoside derivatives of the amine compounds include 12- and 9-(galactosylamino)stearic acid and 12- and 9-(glucosylamino)stearic acid and esters thereof and the corresponding stearic alcohol derivatives.
  • Other possible sugar residues are described below.
  • the sugar residue can be a reducing monosaccharide, disaccharide or oligosaccharide.
  • Suitable sugars include the monosaccharides glucose (Glc), galactose (Gal), mannose (Man), fructose, xylose (Xyl) and arabinose, the disaccharides maltose (Glc-l ⁇ 4-Glc), isomaltose (Glc-l ⁇ 6-Glc), cellobiose (Glc-l ⁇ 4-Glc), gentio- biose (Glc-l ⁇ 6-Glc), laminaribiose (Glc-l ⁇ 3-Glc), melibiose (Gal-l ⁇ 6-Glc), lactose (Gal-l ⁇ 4-Glc), epilactose (Gal-l ⁇ 4-Man), primeverose (Xyl-1 ⁇ 6-Glu) and xylobiose (Xyl-l ⁇ 4-Xyl) and the corresponding trisaccharides such as maltotriose, galacto
  • Di- and higher saccharides wherein the second sugar group is attached to the 2 position of the first sugar are somewhat less useful. Pentasaccharides and higher are also less important. Preference is given to aldoses, in particular non-expensive sugars such as glucose, galactose, lactose and maltose. Examples of groups forming part of the C j -C ⁇ alkyl groups interrupted by one
  • oxygen atoms or imino groups represented by R examples include alkyleneoxy or alkyleneimino groups, such as ethyleneoxy, 1,2-propyleneoxy, 2-hydroxy- 1,3-propyleneoxy, 2,2-bis(hydroxy- methyl)- 1,3-propyleneoxy, ethyleneimino, 1,3-propyleneimino, hexamethyleneimino,
  • the secondary amines can be prepared from the corresponding unsaturated compounds, halogen compounds, ketones or alcohols.
  • a mixture of methyl-9- and -10-aminooctadecanoic acid can be obtained by treatment of methyl oleate with 70% nitric acid and hydrogenation with Raney nickel
  • 12-aminooctadecanoic acid can be obtained from 12-oxooctadecanoic acid by reductive amination with ammonia and a catalyst, of, advantageously, by oximation with anhydrous hydroxylamine in methanol followed by hydrogenation, such as illustrated in the examples.
  • the same procedure can be followed for the corresponding 1-hydroxy compounds, starting from l-hydroxy-9- or -12-octadecanone, respectively.
  • the oximation of oxoalkanoic acids and oxoalkanols is preferably performed using neutral hydroxylamine in a C j -C 3 alcohol, in particular methanol.
  • the reduction thereof is preferably performed using mild temperatures, preferably about room temperature (10-30°C) and using hydrogen under a pressure of e.g. 1.5-5 bar in the presence of a transition metal catalyst, especially palladium on carbon.
  • a transition metal catalyst especially palladium on carbon.
  • the groups R 10 , R 11 and R 12 can be introduced in a manner known per se. If R 10 , R 11 (and R 12 ) are alkyl groups, these can be introduced by reaction of the secondary amine with the corresponding alkyl halide, s ⁇ lphonate, sulphate or the like, such as methyl iodide, diethyl sulphate, butyl bromide. Similarly, groups such as alkenyl (e.g. allyl or octadienyl), alkynyl (e.g. propargyl), benzyl, cycloalkylalkyl, represented by R 12 , can be introduced using the corresponding halide, (methane)sulphonate etc.. Hydroxy- alkyl groups can be introduced using halides or epoxides, such as epichlorohydrine. Acyl groups R such as acetyl are introduced using the appropriate acid anhydride or acid halide.
  • Alkyl or alkanoyl groups substituted by a carboxyl, phospho and/or sulpho group as R 12 include alkyl and alkanoyl groups substituted by one or more acid groups -COOH, -PO(R 9 )(OH), -PO(OR 9 )(OH), -OPO(R 9 )(OH), -OPO(OR 9 )(OH), -SO 3 H or -OSO3H, while the group -PO(R 9 )(OH), -PO(OR 9 )(OH), -SO 3 H can also be directly bound to the nitrogen atom.
  • R represents a hydrogen atom or a C j -Cy hydrocarbon group, such as methyl, ethyl, allyl, butyl, phenyl, cyclohexyl or benzyl.
  • the acid groups can of course be present in ionised form, and in particular as part of zwitter- ions.
  • These compounds can be prepared for example by reaction of the amine, for example: a haloacetic acid resulting in a carboxymethyl derivative; acrylonitrile followed by saponification resulting in a carboxyethyl derivative; a halomethylphosphonic acid resulting in a phosphonomethyl derivative; formaldehyde and an alkylphosphinic acid resulting in an ethylphosphinicomethyl) derivative; hydroxymethylsulphonic acid resulting in a sulphomethyl derivative; chloroethanesulphonic acid resulting in a sulpho- ethyl derivative; ethyleneoxide and chlorosulphonic acid resulting in a sulphatoethyl derivative; chlorosulphonic acid or chlorophosphonic acid resulting in an sulphato or phosphato derivative; succinic anhydride resulting in a succinoyl derivative; or maleic anhydride and sulphite resulting in a ⁇ -sulphosuccino
  • the invention also relates to novel glycosides complying with formula 2,
  • the sugar residue Sac of the glycoside can be a reducing monosaccharide, disaccharide or oligosaccharide as described above.
  • the glycosides according to the invention are obtained from a secondary alcohol or a secondary amine.
  • the secondary alcohol or the secondary amine which, together with the sugar, forms the surface-active glycoside according to the invention, contains at least 9, in particular 12-24 carbon atoms, the hydroxyl group and the amino group, respectively, being located at a distance of at least 4 atoms from the chain ends, such as in 9-octadecanol.
  • the secondary alcohol can optionally contain a second, secondary hydroxyl group.
  • the secondary alcohol contains a carboxyl-derived function such as an alkyl ester, an amide or a mono- or di-alkylamide.
  • one of the two groups R 13 and R in the formulae 1 and 2 is preferably substituted in the manner as indicated, especially by carboxyl or alkoxycarbonyl.
  • suitable hydroxy carboxylic acids are 10-hydroxy ⁇ almitic acid, 9-hydroxystearic acid, 12-hydroxystearic acid, ricinoleic acid (12-hydroxyoleic acid) and dimo ⁇ hecolic acid (9-hydroxy-10,12-octadecadienoic acid).
  • saturated acids such as the amino- and hydroxystearic acids.
  • Starting materials that are most suitable are the alkyl esters and dialkylamides of the hydroxy acids.
  • alkyl means C 1 -C -alkyl, in particular methyl and ethyl.
  • the esters and amides can be reduced afterwards to alcohols and amines, respectively, if desired.
  • the secondary amine can optionally also contain a hydroxyl group.
  • suitable amines are 9- and 12-amino-octadecanoic esters and amides and 9- and 12- amino-octadecanol.
  • the alcohols and amines can optionally contain one or more alkyleneoxy or alkyleneimino groups between the aliphatic residue and the sugar residue, as described above.
  • novel alkyl glycosides can be prepared for example using the Koenigs- Knorr synthesis (Adv. Carbohydr. Chem. Biochem., 34 (1977) 243), starting with a glycosyl halide and the secondary alcohol in the presence of a heavy metal compound such as a silver or mercury compound, in particular a mercury(II) halide with a cata- lytically active amount of iodide ions in an anhydrous solvent such as dichloromethane and a water-binding agent such as molecular sieves.
  • a heavy metal compound such as a silver or mercury compound, in particular a mercury(II) halide with a cata- lytically active amount of iodide ions in an anhydrous solvent such as dichloromethane and a water-binding agent such as molecular sieves.
  • the other hydroxyl groups of the glycoside should be protected as an ester (for example an acetate) or ether (for example a benz
  • the process starts with an imidate ester of the sugar, in particular a trichloroacetic imidate, obtained by reaction of the sugar with trichloroacetonitrile (scc Angew. Chem., Int. Ed. Engl, 25 (1986) 212; Adv. Carbohydr. Chem. Biochem., 50 (1994) 21).
  • imidate ester of the sugar in particular a trichloroacetic imidate
  • the novel alkyl glycosides can be obtained in an advantageous manner by reaction of the glycosyl halide with a hindered amine, such as triethylamine or diisopropylamine, in a polar aprotic solvent such as acetonitrile, propiononitrile, tetrahydrofuran, nitromethane or dimethylformamide, in the presence of a water-binding agent. Yield in the order of 50% can be obtained in this way.
  • any protecting groups such as acetate groups or benzyl groups can be removed, if desired, by hydrolysis or reduction, in a manner known per se.
  • the amine can react with the sugar as such, producing a glycosylamine.
  • this glycosylamine is reduced to the more stabile glycitylamine, the direct bond between R 8 and R 5 /R 6 in formula 2 being hydrogenated.
  • the reduction can for example be performed with sodium borohydride or with hydrogen and a metal catalyst, such as nickel, palladium, platinum, ruthenium or another group VIII metal, optionally on a support such as carbon.
  • the amination and reduction can be carried out in distinct steps. However, higher yields are obtained, when the reductive amination is carried out in a single step, preferably with hydrogen and a catalyst.
  • Solvents to be used include, for example, water, an alcohol or an alcohol-water mixture. It was found that if a slightly less than equivalent amount of alkylamine with respect to sugar is used, the sugar is not reduced and thus the product can be further processed in a more simple manner.
  • the alkyl glycosylamine can also, advantageously, be acylated, resulting in more stabile derivatives, which moreover have useful surfactant properties; in formula 2, Z represents acylimino for these derivatives.
  • the acylation can be effected by treating the alkylglycosylamine with a C j -C 3 carboxylic acid anhydride or halide in a suitable solvent, preferably with a base.
  • the amination of the sugar and the acylation can also be performed by "reactive processing” (see e.g. Tomasik et al., Starch/St ⁇ rke 47 (1995), 96-99, and Narkrugsa et al. Starch/St ⁇ rke 44 (1992), 81-90), i.e. without or with low levels of solvents with mechanical agitation, for example in an extruder.
  • one or more of the primary alcohol groups in the alkyl glycosides or alkyl glycosylamines can be converted to a carboxylic acid group, for example by oxidation with hypochlorite in the presence of 2,2,6,6-tetramethylpiperidine-l-oxyl (TEMPO), or by oxidation with oxygen and a transition metal catalyst.
  • TEMPO 2,2,6,6-tetramethylpiperidine-l-oxyl
  • a further aspect of the invention pertains to surfactant glycosyl amines and glycosides bearing an alkyl group or alkanoyl group having 1-4 carbon atoms substituted by one or more acid groups -COOH, -PO(R 9 )(OH), -PO(OR 9 )(OH), -OPO(R 9 )(OH), -OPO(OR 9 )(OH), -SO 3 H or -OSO 3 H on one or more of the oxygen- (and, if applicable, nitrogen) atoms, while the group -PO(R 9 )(OH), -PO(OR 9 )(OH), -SO 3 H can also be directly bound to an oxygen atom.
  • R represents hydrogen or a hydrocarbon group as defined above.
  • the invention also relates to the use of the derivatives described above as an emulsifier in foodstuffs, as a detergent as an am emulsifier in washing compositions, dish-washing compositions, body care compositions, cosmetics, shampoos, or as a dis- persant for e.g. pesticides etc.
  • Methyl 12-(hydroxyimino)-octadecarioate (example 1) (3.27 g) was hydrogenated during 48 hours in methanol (100 ml) with 10% palladium on activated coal (200 mg), at room temperature and 2.1-2.8 bar of hydrogen pressure. Then the catalyst was removed from the reaction mixture by filtration over Celite . The Celite layer was washed with a total of 150 ml warm (50°C) methanol, and the filtrate was evaporated to dryness. The residue was redissolved in 30 ml hot methanol and this solution was added to 120 ml of distilled water.
  • Methyl 12-aminooctadecanoate was extracted from the aqueous methanol phase with a total of 150 ml of hexane.
  • the organic phase was dried (MgSO 4 ), filtered, and the solvent was evaporated, yielding the title product (3.0 g, 95%).
  • Example 6 Methyl 9-aminooctadecanoate The methods as described in example 5 were used starting with the 9-oxime of example 2. Yield: 3.0 g (96%). 1H (3.150 s, 1H, H-9) and 13 C NMR, FT-IR, MS spectral and analysis data are in accordance with the structure.
  • Example 9 1 -Hydroxy -9- (trimethylammonio)octadecane
  • the product of example 8 is dissolved in dichloromethane and reacted with methyl iodide (6 equivalents) to produce the title product after evaporation.
  • Example 10 Methyl 12-(peracetylgalactosylamino)stearate via Koenings -Knorr reaction
  • Example 11 Methyl 12-galactosylaminostearate
  • the product of the previous example is deacetylated with sodium methoxide in methanol with reflux for 4 h.
  • IR (cm -1 ) 3365 (w); 2936 (s); 2359 (s); 2337 (s); 1651 (s); 1447 (s,w); 1354 (s).
  • Examples 12-15 1 -0-(ll -Methoxycarbonyl-1 -hexylundecyl) - ⁇ -D-glucose,

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Saccharide Compounds (AREA)

Abstract

La présente invention concerne des amines tensio-actifs représentés par la formule générale (1) R?10R11R12N+-CHR2-A1-R1¿. Dans cette formule, A1 est un groupe C¿5?-C11 alkylène. R?1¿ est hydroxyméthyl, carbamoyl, carboxy ou (C¿1?-C4) alcoxycarbonyl. R?2¿ est un groupe C¿5?-C9 alkyl. R?10 et R11¿ représentent chacun un hydrogène ou un groupe C¿1?-C4 alkyl, mais R?10 et R11¿ peuvent aussi, avec l'atome azote, représenter un groupe pyrrolidino, pipéridino ou porpholino. R12 est un C¿1?-C20 alkyl, alcényl, alkynyl, cycloalkyl(alkyl) ou acyl, lequel groupe peut être interrompu par un ou plusieurs atomes d'oxygène ou groupes imino, un groupe C1-C3 alkyl ou C2-C3 alcanoyl substitué par un groupe carboxyl, phospho et/ou sulfo ou un radical sucre. En outre, lorsque R?10¿ est hydrogène, l'atome azote peut également être déprotoné. L'invention concerne également desalkylglucosides tensio-actifs. Ces composés conviennent comme émulsifiants, en composition dans les détergents, et analogues.
PCT/NL1998/000077 1997-02-10 1998-02-10 Amines et glycosides tensio-actifs WO1998034943A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NL1005244A NL1005244C2 (nl) 1997-02-10 1997-02-10 Oppervlakte-actieve aminen en glycosiden.
NL1005244 1997-02-10

Publications (1)

Publication Number Publication Date
WO1998034943A1 true WO1998034943A1 (fr) 1998-08-13

Family

ID=19764397

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/NL1998/000077 WO1998034943A1 (fr) 1997-02-10 1998-02-10 Amines et glycosides tensio-actifs

Country Status (2)

Country Link
NL (1) NL1005244C2 (fr)
WO (1) WO1998034943A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000057698A1 (fr) * 1999-03-29 2000-10-05 Cognis Deutschland Gmbh Emulsions
CN103910771A (zh) * 2014-04-18 2014-07-09 武汉理工大学 一种七-O-乙酰基-1-巯基-β-D-麦芽糖的合成方法
US10472364B2 (en) 2016-09-09 2019-11-12 Calithera Biosciences, Inc. Ectonucleotidase inhibitors and methods of use thereof
US10570167B2 (en) 2016-12-22 2020-02-25 Calithera Biosciences, Inc. Ectonucleotidase inhibitors and methods of use thereof
US11078228B2 (en) 2018-06-21 2021-08-03 Calithera Biosciences, Inc. Ectonucleotidase inhibitors and methods of use thereof

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2312967A (en) * 1940-07-18 1943-03-02 Du Pont Chemical process and product
US2610212A (en) * 1950-04-24 1952-09-09 Gen Mills Inc Synthesis of amino acids
GB2237018A (en) * 1989-08-18 1991-04-24 Medeva Plc Secondary alcohols and compositions containing fatty acids or esters
WO1994021655A1 (fr) * 1993-03-23 1994-09-29 Berol Nobel Ab Glucoside d'alkyle et son utilisation
WO1995021182A1 (fr) * 1994-02-03 1995-08-10 Henkel Kommanditgesellschaft Auf Aktien Pseudoceramides
EP0705599A1 (fr) * 1994-09-29 1996-04-10 L'oreal Utilisation de N-(hydroxyalkyl) carbamates d'alkyle dans une composition cosmétique en tant que tensioactifs
EP0745608A2 (fr) * 1995-05-29 1996-12-04 Hoechst Aktiengesellschaft Nouveaux lipides du glucose et sophorose, procédé de leur préparation et leur utilisation

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2312967A (en) * 1940-07-18 1943-03-02 Du Pont Chemical process and product
US2610212A (en) * 1950-04-24 1952-09-09 Gen Mills Inc Synthesis of amino acids
GB2237018A (en) * 1989-08-18 1991-04-24 Medeva Plc Secondary alcohols and compositions containing fatty acids or esters
WO1994021655A1 (fr) * 1993-03-23 1994-09-29 Berol Nobel Ab Glucoside d'alkyle et son utilisation
WO1995021182A1 (fr) * 1994-02-03 1995-08-10 Henkel Kommanditgesellschaft Auf Aktien Pseudoceramides
EP0705599A1 (fr) * 1994-09-29 1996-04-10 L'oreal Utilisation de N-(hydroxyalkyl) carbamates d'alkyle dans une composition cosmétique en tant que tensioactifs
EP0745608A2 (fr) * 1995-05-29 1996-12-04 Hoechst Aktiengesellschaft Nouveaux lipides du glucose et sophorose, procédé de leur préparation et leur utilisation

Non-Patent Citations (12)

* Cited by examiner, † Cited by third party
Title
APPL. MICROBIOL., vol. 14, no. 3, 1966, pages 308 - 319 *
CHEMICAL ABSTRACTS, vol. 112, no. 4, 22 January 1990, Columbus, Ohio, US; abstract no. 23747u, Q.YUAN ET AL.: "Extraction of Tungsten and Molybdenum by Various Organic Compounds as Extractants." XP002067134 *
CHEMICAL ABSTRACTS, vol. 113, no. 9, 27 August 1990, Columbus, Ohio, US; abstract no. 77641u, C.LIU: "Synthesis of Some Secondary Amine Ligands." page 717; column 2; XP002067135 *
CHEMICAL ABSTRACTS, vol. 118, no. 1, 4 January 1993, Columbus, Ohio, US; abstract no. 6597b, N.G.ZHUKOVA ET AL.: "Anion-Exchange Extractants With Regulable Selectivity." page 703; column 1; XP002067133 *
CHEMICAL ABSTRACTS, vol. 54, no. 8, 25 April 1960, Columbus, Ohio, US; abstract no. 7975e, K.HOWORKA ET AL.: "Determination of Organic Nitrogen Bases. I. Quaternary Ammonium Salts." XP002067132 *
CHEMICAL ABSTRACTS, vol. 64, no. 13, 20 June 1966, Columbus, Ohio, US; abstract no. 20545b, H.J.HUECK ET AL.: "Bacteriostatic, Fungistatic, and Algistatic Activity of Fatty Nitrogen Compounds." XP002067131 *
HUAXUE SHIJI, vol. 11, no. 6, 1989, pages 369 - 371 *
M.BAH: "Isolation and Structural Characterization of New Glycolipid Ester Type Dimers from the Resin of Ipomoea Tricolor (Convolvulaceae).", TETRAHEDRON., vol. 53, no. 27, 7 July 1997 (1997-07-07), OXFORD GB, pages 9007 - 9022, XP002052096 *
PHARM. ZENTRALHALLE, vol. 98, 1959, pages 538 - 545 *
S.LECLERCQ ET AL.: "Biosynthesis of hte Solenposins, Venom Alkaloids of the Fire Ants.", NATURWISSENSCHAFTEN, vol. 83, no. 5, 1996, pages 222 - 225, XP002067130 *
TSVETN. MET., no. 3, 1991, pages 47 - 48 *
XIYOU JINSHU, vol. 8, no. 3, 1989, pages 15 - 19 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000057698A1 (fr) * 1999-03-29 2000-10-05 Cognis Deutschland Gmbh Emulsions
CN103910771A (zh) * 2014-04-18 2014-07-09 武汉理工大学 一种七-O-乙酰基-1-巯基-β-D-麦芽糖的合成方法
US10472364B2 (en) 2016-09-09 2019-11-12 Calithera Biosciences, Inc. Ectonucleotidase inhibitors and methods of use thereof
US11208414B2 (en) 2016-09-09 2021-12-28 Calithera Biosciences, Inc. Ectonucleotidase inhibitors and methods of use thereof
US10570167B2 (en) 2016-12-22 2020-02-25 Calithera Biosciences, Inc. Ectonucleotidase inhibitors and methods of use thereof
US11034715B2 (en) 2016-12-22 2021-06-15 Calithera Biosciences, Inc. Ectonucleotidase inhibitors and methods of use thereof
US11078228B2 (en) 2018-06-21 2021-08-03 Calithera Biosciences, Inc. Ectonucleotidase inhibitors and methods of use thereof

Also Published As

Publication number Publication date
NL1005244C2 (nl) 1998-08-18

Similar Documents

Publication Publication Date Title
US9309276B2 (en) Synthetic lipid A derivative
EP0192296B1 (fr) Dérivés de disaccharides et trisaccharides du type "Lipid A"
US6624190B2 (en) 2-acylamino-2-deoxy-glucono-1,5-lactones, a method for the production thereof, compositions containing them, and uses thereof
EP1674476B1 (fr) Glycoside de carbonate de glycerol
EP0212400B1 (fr) Méthode de préparation de dérivés de la sphingosine
WO1998034943A1 (fr) Amines et glycosides tensio-actifs
E. Aly et al. The Dimethylmaleoyl Group as Amino Protective Group–Application to the Synthesis of Glucosamine‐Containing Oligosaccharides
Suhr et al. Synthesis of glycosyl glycerols and related glycolipids
Ross et al. Parasite glycoconjugates. Part 11. 1 Preparation of phosphodisaccharide synthetic probes, substrate analogues for the elongating α-D-mannopyranosylphosphate transferase in the Leishmania
US5541341A (en) Nonionic glycasuccinimide surfactants and a process for their manufacture
JP2923309B2 (ja) ガングリオシド類
Yamanoi et al. BF3· OEt2 Enhanced Yb (OTf) 3-Promoted Glycosidation of 1-O-Acyl-D-Glucopyranose
Venkannababu et al. Regulosides A–C: glycosphingolipids from the starfish Pentaceraster regulus
Seifert et al. Syntheses of α-dystroglycan derived glycosyl amino acids carrying a novel mannosyl serine/threonine linkage
US5864022A (en) Process for the manufacture of 3-amino-substituted glycosylated bile acids
Laurent et al. Syntheses of α-D-galactosamine neoglycolipids
Wessel et al. Selectively Deoxygenated Derivatives of β-Maltosyl-(1→ 4)-Trehalose as Biological Probes
JPH10324694A (ja) リピッドａ１位カルボン酸誘導体
Lafont et al. Syntheses of d-Glucosaminyl Bolaamphiphiles1
JP4162739B2 (ja) グリコシド誘導体の製造法
JPH03264595A (ja) 新規なグリコシル化方法
Walczak et al. Synthesis of 1‐[2, 3‐dideoxy‐3‐(3‐hydroxypropyl)‐d‐pentofuranosyl] thymines
Bogaert et al. Non‐reductive coupling of branched amino fatty acid esters with mono and disaccharides: synthesis of a new class of alkyl glycosylamines
Ogawa et al. [9] Chemical synthesis of glycosylamide and cerebroside analogs composed of carba sugars
Qiu et al. Design and Synthesis of Gentiohexaosyl Derivatives for an ANP Receptor Antagonist, HS-142–1

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): JP US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FI FR GB GR IE IT LU MC NL PT SE

121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase
点击 这是indexloc提供的php浏览器服务，不要输入任何密码和下载