EP2920200A1 - Substituierte anionische verbindungen aus einem rückgrat aus einer diskreten anzahl von saccharideinheiten - Google Patents

Substituierte anionische verbindungen aus einem rückgrat aus einer diskreten anzahl von saccharideinheiten

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Publication number
EP2920200A1
EP2920200A1 EP13801655.5A EP13801655A EP2920200A1 EP 2920200 A1 EP2920200 A1 EP 2920200A1 EP 13801655 A EP13801655 A EP 13801655A EP 2920200 A1 EP2920200 A1 EP 2920200A1
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EP
European Patent Office
Prior art keywords
function
radical
anionic compounds
chosen
substituted
Prior art date
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Application number
EP13801655.5A
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English (en)
French (fr)
Inventor
Gérard Soula
Emmanuel DAUTY
Richard Charvet
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Adocia SAS
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Adocia SAS
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Publication date
Priority claimed from FR1260808A external-priority patent/FR2997952B1/fr
Priority claimed from FR1260855A external-priority patent/FR2997857B1/fr
Priority claimed from FR1351199A external-priority patent/FR3001895B1/fr
Application filed by Adocia SAS filed Critical Adocia SAS
Publication of EP2920200A1 publication Critical patent/EP2920200A1/de
Withdrawn legal-status Critical Current

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    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • A61K38/22—Hormones
    • A61K38/28—Insulins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
    • A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • 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
    • C07H15/18—Acyclic radicals, substituted by carbocyclic rings
    • 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
    • C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof

Definitions

  • Substituted anionic compounds consisting of a backbone formed of a discrete number of saccharide units
  • the present invention relates to anionic compounds for therapeutic and / or prophylactic use, for the administration of principle (s) active (s) to humans or animals.
  • anionic compounds according to the invention whose skeleton consists of saccharide units containing carboxyl groups have, because of their structure and their biocompatibility, a certain interest for the pharmaceutical industry, especially for the stabilization of principles. active for example protein.
  • polymers or oligomers are defined by their degree of polymerization DP which is the average number of repeating units (monomers) per polymer chain. It is calculated by dividing the number average molar mass by the average mass of the repeating unit. They are also defined by the chain length distribution, also called polydispersity index (Ip).
  • polymers are therefore compounds consisting of chains whose lengths are statistically variable which have a great wealth of possible interaction sites with protein active ingredients. This potential for multiple interactions could lead to a lack of specificity in terms of interaction, whereas a smaller and better defined molecule could be more specific in this respect.
  • a polymer chain can interact with different sites present on a protein principle but can also because of the length of the chain interact with several protein principles resulting in a bridging phenomenon.
  • This bridging phenomenon may for example lead to the aggregation of proteins or an increase in viscosity.
  • the use of a small molecule with a well-defined skeleton makes it possible to minimize these bridging phenomena.
  • a molecule with a well-defined skeleton is generally more easily traceable (MS / MS for example) in biological media during pharmacokinetic or ADME experiments (administration, distribution, metabolism, elimination) by compared to a polymer that generally gives a very diffuse and noisy signal in mass spectrometry.
  • the anionic compounds according to the invention consist of a skeleton formed of a discrete number u between 1 and 8
  • identical or different saccharide units also have the property of creating interactions with active principles, for example protein.
  • the present invention thus aims to provide anionic compounds for stabilization, administration and delivery of active ingredients, which can be prepared by relatively simple methods to implement.
  • the present invention is thus intended to provide anionic compounds capable of allowing the stabilization, administration and delivery of active ingredients of great diversity.
  • the invention also aims at obtaining anionic compounds which may have sufficiently fast biodegradability and suitable for their use in the preparation of a broad category of pharmaceutical formulations, including for medicaments intended for chronic administration and / or high frequency.
  • the invention aims to provide anionic compounds meeting the constraints established by the pharmaceutical industry, particularly in terms of stability under normal conditions of storage and storage and especially in solution.
  • the substituted anionic compounds according to the invention make it possible to prepare non-turbid solutions in the presence of certain "model" proteins for the formulation such as lysozyme, which is not possible with certain compounds. polymers, but are nevertheless able to interact with model proteins such as albumin. This duality makes it possible to modulate their properties and to obtain good excipient candidates for the formulation of proteinaceous active principles without the disadvantages presented by some of the compounds described in the prior art.
  • the present invention relates to substituted anionic compounds, in the solute or mixed state, consisting of a skeleton formed of a discrete number u inclusive of 1 and 8 (1 u ⁇ 8) of identical saccharide units or different, bonded by identical or different glycosidic moieties, said saccharide units being selected from the group consisting of pentoses, hexoses, uronic acids, N-acetyl hexosamines cyclic form or open reduced form, characterized in that they are substituted with: a) at least one substituent of general formula I;
  • the radical - [Q] - is derived from a C3-C15 carbon chain, optionally branched or substituted, optionally saturated and / or optionally comprising one or more rings and / or comprising at least one heteroatom selected from O, N and S and at least one L function selected from amine and alcohol functions, said radical - [Q] - being attached to the backbone of the compound via a linker arm R x to which it is linked by a function T or directly linked to the skeleton by a function G,
  • the radical - [Q] - is derived from a C2-C15 carbon chain, optionally branched or substituted, optionally unsaturated and / or optionally comprising one or more rings and / or or comprising at least one heteroatom selected from O, IM and S and at least one L function selected from amine and alcohol functions and bearing n radical (s) R 2 , said radical - [Q] - being attached to the backbone of the compound via a link arm Ri to which it is linked by a function T or directly linked to the backbone by a function G,
  • radical -Rj- being:
  • a 1, C2 to C15 optionally substituted and / or comprising at least one heteroatom chosen from O, N and S and at least one acid function before the reaction with the radical - [Q] -, said chain being linked to the radical - [Q] - by a function T resulting from the reaction of the acid function of the radical -R with an alcohol or amine function of the precursor of the radical - [Q] -, and said radical Ri is attached to the backbone by means of a function F resulting from a reaction between a hydroxyl function or an acid function carboxylic acid borne by the backbone and a function or substituent carried by the radical precursor -Ri,
  • the radical -R 2 is a C1 to C30 carbon chain, optionally branched or substituted, optionally unsaturated and / or optionally comprising one or more rings and / or one or more heteroatoms selected from O, N and S; it forms with the radical - [Q] - a function Z resulting from a reaction between the alcohol, amine or acid functions carried by the precursors of the radical -R 2 and the radical - [Q] -.
  • F is a function chosen from ether, ester, amide or carbamate functions
  • T is a function chosen from amide or ester functions
  • Z is a function chosen from ester, carbamate, amide or ether functions
  • G is a function chosen from the ester, amide or carbamate functions
  • N 0, 1 or 2
  • M is equal to 1 or 2
  • u is between 3 and 8
  • u is between 3 and 5
  • u is equal to 3.
  • L is an amine function
  • L is an alcohol function
  • 0.5 ⁇ i + j ⁇ 3.
  • m 2.
  • m 1.
  • n 2.
  • n 1.
  • n-0 In one embodiment, n-0.
  • the anionic compounds according to the invention are characterized in that the radical - [Qj- is derived from an alpha-amino acid.
  • the anionic compounds according to the invention are characterized in that the alpha-amino acid is chosen from the group comprising alpha-methyl-phenylalanine, alpha-methyl-tyrosine, O-methyl tyrosine, alpha-phenylglycine, 4-hydroxyphenylglycine, 3,5-dihydroxyphenylglycine, in their L, D or racemic forms.
  • the anionic compounds according to the invention are characterized in that the alpha amino acid is chosen from alpha natural amino acids.
  • the anionic compounds according to the invention are characterized in that the natural alpha amino acid is chosen from the hydrophobic amino acids chosen from the group comprising tryptophan, leucine and alanine. isoleucine, glycine, phenylalanine, tyrosine, valine, in their L, D or racemic forms.
  • the anionic compounds according to the invention are characterized in that the natural alpha amino acid is chosen from polar amino acids chosen from the group comprising aspartic acid, glutamic acid, lysine, serine, threonine, in their L, D or racemic forms.
  • the precursor of the radical - [Q] - is chosen from diamines.
  • the diamines are chosen from the group consisting of ethylene diamine and lysine and its derivatives.
  • the diamines are chosen from the group consisting of diethyleneglycoldiamine and triethyleneglycoldiamine.
  • the precursor of the radical - [Q] - is chosen from aminoalcohols.
  • the aminoalcohols are chosen from the group consisting of ethanolamine, 2-aminopropanol, isopropanolamine, 3-amino-1,2-propanediol, diethanolamine and diisopropanolamine. , tromethamine (Tris) and 2- (2-aminoethoxy) ethanol.
  • the precursor of the radical - [Q] - is chosen from dialcohols.
  • dialcohols are chosen from the group consisting of glycerol, diglycerol and triglycerol.
  • the dialcohol is triethanolamine.
  • dialcohols are chosen from the group consisting of diethylene glycol and triethylene glycol.
  • the dialcohols are selected from the group consisting of polyethylene glycols.
  • the precursor of the radical - [Q] - is chosen from among the trialcools.
  • the trihydric alcohol is triethanolamine.
  • the present invention when the radical - [Q] - is chosen from amino acids, the present invention relates to substituted anionic compounds, in the isolated state or in a mixture, consisting of a skeleton formed of a discrete number u of between 1 and 8 (1 ⁇ u ⁇ 8) of identical or different saccharide units, linked by identical or different glycoside bonds, said saccharide units being chosen from the group consisting of pentoses, hexoses, uronic acids, N-acetylhexosamines in cyclic form or in open reduced form, characterized in that they are substituted by: a) at least one substituent of general formula II ⁇
  • radical - [AA] - denotes an amino acid residue comprising a C3-C15 carbon chain directly linked to the backbone by a function G '
  • radical - [AA] - denotes an amino acid residue comprising a C2-C15 carbon chain bearing n -R 2 radical (s) attached to the backbone of the compound by via a linker R 1 to which it is bound by an amide function or directly linked to the backbone by a function G ', the radical -Ri being:
  • radical -R 2 is a carbon chain C1 to C30, optionally branched or substituted, optionally unsaturated and / or optionally comprising one or more rings and / or one or more heteroatom (s) selected from O, N and S; with the amino acid residue - [AA] - it forms a Z 'function resulting from a reaction between a hydroxyl, acidic or amine functional group carried by the precursor of the radical - R ? and an acid,
  • F is a function selected from ether, ester, amide or carbamate functions
  • G ' is a function selected from ester, amide or carbamate functions
  • Z' is a function chosen from ester, amide or carbamate functions
  • n is equal to 0 , 1 or 2
  • n 1 or 2
  • the degree of substitution of the saccharide units, j, in - [Ri] a - [[AA] - [R 2 ] n ] m being between 0.01 and 6, 0.01 ⁇ j ⁇ 6 and, optionally, or more substituents -R'i, the substituent -R being a C2-C15 carbon chain, optionally substituted and / or comprising at least one heteroatom selected from O, N and S and at least one acid function in the form of cation salt said chain being linked to the backbone by a function F 'resulting from a reaction between a hydroxyl function or a carboxylic acid function carried by the backbone and a function or a substituent carried by the precursor of the substituent -R, the degree of substitution of the saccharide units, i, -R'i being between 0 and 6-j , 0 ⁇ i ⁇ 6-j and,
  • F ' is an ether, ester, amide or carbamate function
  • u is between 3 and 8
  • u is between 3 and 5
  • u is equal to 3.
  • 0 05 ⁇ j ⁇ 6 0 05 ⁇ j ⁇ 6.
  • 0 s ⁇ j 0 s ⁇ j ⁇ 1, 2.
  • 0 ⁇ i 3.
  • m 2.
  • m 1.
  • n 2.
  • n 1.
  • n 0.
  • the present invention relates to substituted anionic compounds consisting of a backbone formed of a discrete number u of between 1 and 8 (1 u ⁇ 8) of identical or different saccharide units, linked by identical or different glycoside bonds, said saccharide units being chosen from the group consisting of pentoses, hexoses, uronic acids, N-acetylhaxoamines in cyclic form or in open reduced form, characterized in that they are substituted, of statistically by:
  • radical - [AA] - denotes an amino acid residue optionally bearing n radical (aux) R 2 attached to the backbone of the compound via a linking arm i or directly linked to the backbone by a function G '
  • a 1 in C2 to C15 optionally substituted and / or comprising at least one heteroatom chosen from O, N and S and at least one acid function before the reaction with the amino acid, said chain forming with the amino acid residue - [AA] - an amide bond, and is attached to the backbone using a function F resulting from a reaction between a hydroxyl function or a carboxylic acid function carried by the backbone and a function carried by the precursor of -Ri-,
  • the radical -R 2 is a C1 to C30 carbon chain, optionally branched or substituted, optionally unsaturated and / or optionally comprising one or more rings and / or one or more heteroatoms selected from O, N and S; it forms with the amino acid residue - [AA] - an ester, carbamate, amide, ether bond resulting from a reaction between a function carried by -R 2 and a function carried by the precursor of the radical - [AA] ] -,
  • F is an ether, ester, amide or carbamate function
  • G ' is an ester, amide or carbamate function
  • N 0, 1 or 2
  • M is equal to 1 or 2
  • R 1 being a carbon chain C2 to C15, optionally substituted and / or comprising at least one heteroatom selected from O, N and S and at least one acidic function in the form of alkali metal salt, said chain being linked to the skeleton by a function F 'resulting from a reaction between a hydroxyl function or a carboxylic acid functional group carried by the backbone and a function carried by the precursor of -R' t ,
  • the salt-forming acid functions li fibers carried by R are as alkali cation salts
  • F ' is an ether, ester, amide or carbamate function
  • u is between 3 and 5
  • u is equal to 3.
  • 0.05 ⁇ j ⁇ 6 In one embodiment, 0.05 ⁇ j ⁇ 4.
  • m 2.
  • m 1.
  • n 2.
  • n 1.
  • n 0.
  • the substituted anionic compound is chosen from substituted anionic compounds, in the isolated state or in a mixture, consisting of a backbone formed of a discrete number u of between 1 and 8 (1 ⁇ u ⁇ 8) identical or different saccharide units, linked by identical or different glycoside bonds, said saccharide units being chosen from the group consisting of hexoses, in cyclic form or in open reduced form, characterized in that they are substituted with: a) at least one substituent of general formula V
  • a 1, C2 to C15 optionally substituted and / or comprising at least one heteroatom chosen from O, N and S and at least one acid function before the reaction with the amino acid, said chain forming with the amino acid residue - [AA] an amide function, and is attached to the backbone using a function F a resulting from a reaction between a hydroxyl function carried by the backbone and a function or a substituent carried by the precursor of the radical -Ri ⁇ ,
  • F a is a function chosen from ether, ester or carbamate functions
  • G a is a carbamate function
  • n 1 or 2
  • the degree of substitution of the saccharide units, j, in - [Ri] a - [AA] m being strictly greater than 0 and less than or equal to 6, 0 ⁇ j ⁇ 6 and, optionally, one or more substituents -R'i , the substituent -R being a C2-C15 carbon chain, optionally substituted and / or comprising at least one heteroatom selected from O, N and S and at least one acidic function in the form of alkali metal salt, said chain being linked to backbone by a function F ' a resulting from a reaction between a hydroxyl function or a carboxylic acid function carried by the backbone and a function or substituent carried by the precursor of the substituent -R' lf
  • F ' a is an ether, ester or carbamate function, the degree of substitution of the saccharide units, i, in -R, being between 0 and 6-j, 0 ⁇ i ⁇ 6-j and,
  • F 3 and G 3 are identical or different
  • glycosidic bonds being chosen from the group consisting of glycoside bonds of (1,1), (1,2), (1,3), (1,4) or (1,6) type, in an alpha or beta geometry,
  • the anionic compounds according to the invention are characterized in that the radical - [AA] - is derived from an alpha-amino acid.
  • the anionic compounds according to the invention are characterized in that the alpha-amino acid is chosen from the group comprising alpha-methyl-phenylalanine, alpha-methyl-tyrosine, O-methyl tyrosine, alpha-phenylglycine, 4-hydroxyphenylglycine, 3,5-dihydroxyphenylglycine, in their L, D or racemic forms.
  • the anionic compounds according to the invention are characterized in that the alpha amino acid is chosen from natural alpha amino acids.
  • the anionic compounds according to the invention are characterized in that the natural alpha amino acid is chosen from the hydrophobic amino acids chosen from the group comprising tryptophan, leucine and alanine. isoleucine, glycine, phenylalanine, tyrosine, valine, in their L, D or racemic forms.
  • the anionic compounds according to the invention are characterized in that the natural alpha amino acid is chosen from polar amino acids chosen from the group comprising aspartic acid and glutamic acid. lysine, serine, threonine, in their L, D or racemic forms.
  • the substituted anionic compounds are characterized in that they are chosen from substituted anionic compounds with substituents of formulas I, II or V in which a is equal to 0.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted by substituents of formula I in which G is an ester function.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted by substituents of formula I in which G is an amide function. In one embodiment, the substituted anionic compounds are characterized in that they are chosen from substituted anionic compounds with substituents of formula I in which G is a carbamate function.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula II in which G 'is an ester function.
  • the substituted anionic compounds are characterized in that they are chosen from substituted anionic compounds with substituents of formula II in which G 'is an amide function.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula II in which G 'is a carbamate function.
  • the substituted anionic compounds are characterized in that they are chosen from substituted anionic compounds with substituents of formula I, II or V in which a is equal to 1.
  • the substituted anionic compounds are characterized in that they are chosen from substituted anionic compounds with substituents of formula I or II in which F is an ether function.
  • the substituted anionic compounds are characterized in that they are chosen from substituted anionic compounds with substituents of formula I or II in which F is an ester function.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula I or II in which F is an amide function.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula I or II in which F is a carbamate function.
  • the substituted anionic compounds are characterized in that they are chosen from anionic compounds substituted with substituents of formula V in which F a is an ether function.
  • the substituted anionic compounds are characterized in that they are chosen from anionic compounds substituted with substituents of formula V in which F a is an ester function.
  • the substituted anionic compounds are characterized in that they are chosen from substituent compounds substituted by substituents of formula V in which F a is a carbamate function. In one embodiment, the substituted anionic compounds are characterized in that they are chosen from substituted anionic compounds with substituents of formula I in which T is an amide function.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formulas I in which T is an ester function.
  • the substituted anionic compounds are characterized in that they are chosen from the substituted anionic compounds with substituents of formulas I in which T is an amide function, and F is an ether function.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted by substituents of formulas I in which T is an amide function, and F is an ester function.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted with substituents of the formulas I in which T is an amide function, and F is a ca rbamate function.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted by substituents of formulas I in which T is an amide function, and F is an amide function.
  • the substituted anionic compounds are characterized in that they are chosen from substituted anionic compounds with substituents of formulas I in which T is an ester function, and F is an ether function.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted with substituents of formulas I in which T is an ester function, and F is an ester function.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted by substituents of formulas I in which T is an ester function, and F is a carbamate function. In one embodiment, the substituted anionic compounds are characterized in that they are selected from anionic compounds substituted with substituents of formulas I in which T is an ester function, and F is an amide function.
  • the substituted anionic compounds are characterized in that they are chosen from substituted anionic compounds with substituents of formula I or II in which F 'is an ether function.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula I or II in which F is an ester function.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula I or II in which F 'is an amide function.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted by substituents of formula I or II wherein F 'is a carbamate function.
  • the substituted anionic compounds are characterized in that they are chosen from substituted anionic compounds with substituents of formula I or II in which F a is an ether function.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula I or II in which F a is an ester function.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula I or II in which F a is a carbamate function.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula I or II in which F a 'is an ether function.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula I or II in which F a 'is an ester function.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula I or II in which F a 'is a carbamate function. In one embodiment, the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula I or II in which F and F 'are identical.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula I or II in which F and F 'are ether functions.
  • the substituted anionic compounds are characterized in that they are chosen from substituted anionic compounds with substituents of formula I or II in which F and F 'are ester functions.
  • the substituted anionic compounds are characterized in that they are chosen from substituted anionic compounds with substituents of formula I or II in which F and F 'are amide functions.
  • the substituted anionic compounds are characterized in that they are chosen from the substituted anionic compounds with substituents of formula I or II in which F and F 'are carbamate functions.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula I or II or V in which when the radical -Ri is a carbon chain it optionally comprises a heteroatom selected from the group consisting of O, N and S.
  • the substituted anionic compounds are characterized in that they are chosen from anionic compounds substituted with substituents of formula I or II or V in which the radical -Ftr is chosen from radicals of formulas III and IV below:
  • O and p are the same or different, greater than or equal to 1 and less than or equal to 12, and,
  • R 3; R 3, R 4 and R ' which are identical or different, are chosen from the group consisting of a hydrogen atom, a linear, branched, saturated or unsaturated alkyl; or cyclic C1 to C6, benzyl, C7 to C10 alkylaryl and optionally having heteroatoms selected from the group consisting of O, N and / or S, or functions selected from the group consisting of carboxylic acid functions , amine, alcohol or thiol,
  • the substituted anionic compounds are characterized in that they are chosen from anionic compounds substituted with substituents of formula I or II or V in which the radical -Ri before attachment to the radical - [- AA] - or to the radical - [Q] - is -CH 2 -COOH, and after attachment is -CH 2 -.
  • the substituted compounds are characterized in that they are chosen from substituted anionic compounds with substituents of formula I or II or V in which the radical -RI- before attachment to the radical - [AA] ] - or to the radical - [Q] -, is a carbon chain C2 to C10 carrying a carboxylic acid group and after attachment is a carbon chain C2 to C10.
  • the substituted compounds are characterized in that they are chosen from substituted anionic compounds with substituents of formula I or II or V in which the radical -RI- before attachment to the radical - [AA] ] - or to the radical - [Q] -, is a carbon chain C2 to C10 carrying a carboxylic acid group and after attachment is a carbon chain C2 to C10.
  • the substituted compounds are characterized in that they are chosen from substituted anionic compounds with substituents of formula I or II or V in which the radical -RI- before attachment to the radical - [AA] ] - or to the radical - [Q] -, is a C2 to C5 carbon chain carrying a carboxylic acid group and after attachment is a C2 to C5 carbon chain.
  • the substituted compounds are characterized in that they are chosen from substituted anionic compounds with substituents of formula I or II or V in which the radical -RI- before attachment to the radical - [AA] ] - or to the radical - [Q] -, is a C2 to C5 carbon chain carrying a carboxylic acid group and after attachment is a C2 to C5 carbon chain.
  • the substituted anionic compounds are characterized in that they are chosen from anionic compounds substituted with substituents of formula I or II or V in which the radical - i - before attachment to the radical - [ AA] - or to the radical - [Q] -, is chosen from the following groups, in which * represents the site of attachment to F:
  • alkali metal salt salts selected from the group consisting of Na + or K + .
  • the substituted anionic compounds are characterized in that they are chosen from anionic compounds substituted with substituents of formula I or II or V in which the radical -R t - before attachment to the radical - [AA] - or radical - [Q] -, is derived from citric acid.
  • the substituted anionic compounds are characterized in that they are chosen from anionic compounds substituted with substituents of formula I or II or V in which the radical - i - before attachment to the radical - [ AA] - or radical - [Q] -, is derived from malic acid.
  • the substituted anionic compounds are characterized in that they are chosen from substituted anionic compounds with substituents of formula I or II or V and are not substituted with substituents -R'I
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula I or II or V in which when the substituent -R is a carbon chain it comprises optionally a heteroatom selected from the group consisting of O, N and S.
  • the substituted anionic compounds are characterized in that they are chosen from substituted anionic compounds with substituents of formula I or II or V in which the substituent -R is chosen from radicals of formulas III and IV following
  • O and p are the same or different, greater than or equal to 1 and less than or equal to 12, and, R 3 , R 3, R and R ', which are identical or different, are chosen from the group consisting of a hydrogen atom, a saturated or unsaturated, linear, branched or cyclic C1 to C6 alkyl, a benzyl, an alkyl-aryl and optionally comprising heteroatoms selected from the group consisting of O, IM and / or S, or functions selected from the group consisting of carboxylic acid, amine, alcohol or thiol functions,
  • the substituted compounds are characterized in that they are chosen from anionic compounds substituted with substituents of
  • the substituted compounds are characterized in that they are chosen from anionic compounds substituted with substituents of
  • [AA] - or radical - [Q] - is a C2 to C10 carbon chain carrying a carboxylic acid group and after attachment is a C2 to C10 carbon chain.
  • the substituted compounds are characterized in that they are chosen from anionic compounds substituted with substituents of formula I or II or V in which the radical -R'I- before attachment to the radical -
  • [AA] - or radical - [Q] - is a C2 to C10 carbon chain carrying a carboxylic acid group and after attachment is a C2 to C10 carbon chain.
  • the substituted compounds are characterized in that they are chosen from anionic compounds substituted with substituents of formula I or II or V in which the radical -R'I- before attachment to the radical -
  • [AA] - or radical - [Q] - is a C2 to C5 carbon chain carrying a carboxylic acid group and after attachment is a C2 to C5 carbon chain.
  • the substituted compounds are characterized in that they are chosen from anionic compounds substituted with substituents of formula I or II or V in which the radical -R'I- before attachment to the radical -
  • [AA] - or radical - [Q] - is a C2 to C5 carbon chain carrying a carboxylic acid group and after attachment is a C2 to C5 carbon chain.
  • the substituted anionic compounds are characterized in that they are chosen from substituent compounds substituted by substituents of formula I or II in which the substituent -R'i is chosen from the following groups, in which * represents the site of attachment to F: or their alkali metal salt salts selected from the group consisting of Na + or K + .
  • the substituted anionic compounds are characterized in that they are chosen from substituent compounds substituted with substituents of formula V in which the -R substituent is chosen from the following groups, in which * represents the site of attachment to F has :
  • alkaline cation salts selected from the group consisting of Na + or K ⁇
  • the substituted anionic compounds are characterized in that they are chosen from anionic compounds substituted with substituents of formula I or II or V in which the -R substituent is derived from citric acid. .
  • the substituted anionic compounds are characterized in that they are chosen from substituted anionic compounds with substituents of formula I or II or V in which the -R substituent is derived from malic acid. .
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted by substituents of formula I in which Z is an ester function.
  • the substituted anionic compounds are characterized in that they are chosen from substituted anionic compounds with substituents of formula I in which Z is an amide function.
  • the substituted anionic compounds are characterized in that they are selected from the substituted anionic compounds with substituents of formula I wherein Z is a carbamate function. [000191] In one embodiment, the substituted anionic compounds are: characterized in that they are selected from substituted anionic compounds with substituents of formula II wherein Z 'is an ester function.
  • the substituted anionic compounds are: characterized in that they are selected from the anionic compounds substituted by substituents of formula II in which Z 'is an amide function.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula II in which Z 'is a carbamate function.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted with substituents of formula I in which Z is an ester function, T is an amide function, and F is an ether function.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted by substituents of formula I in which Z is an ester function, T is an amide function, and F is an ester function.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted by substituents of formula I in which Z is an ester function, T is an amide function, and F is a carbamate function.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted with substituents of formula I in which Z is an ester function, T is an amide function, and F is an amide function.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted by substituents of formula I in which Z is an ester function, T is an ester function, and F is an ether function.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula I in which Z is an ester function, T is an ester function, and F is an ester function.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula I wherein Z is an ester function, T is an ester function, and F is a carbamate function.
  • the substituted anionic compounds are characterized in that they are chosen from substituted anionic compounds with substituents of formula I in which Z is an ester function, T is an ester function, and F is an amide function.
  • the substituted anionic compounds are characterized in that they are selected from substituted anionic compounds with substituents of formula I in which Z is an amide function, T is an amide function, and F is an ether function.
  • the substituted anionic compounds are characterized in that they are chosen from substituted anionic compounds with substituents of formula I in which Z is an amide function, T is an amide function, and F is an ester function.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula I in which Z is an amide function, T is an amide function, and F is a carbamate function.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted by substituents of formulas I in which Z is an amide function, T is an amide function, and F is an amide function.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted by substituents of formula I in which Z is an amide function, T is an ester function, and F is an ether function.
  • the substituted anionic compounds are characterized in that they are chosen from substituent compounds substituted by substituents of formula I in which Z is an amide function, T is an ester function, and F is an ester function.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted with substituents of formulas I in which Z is an amide function, T is an ester function, and F is a carbamate function. In one embodiment, the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted by substituents of formulas I in which Z is an amide function, T is an ester function, and F is an amide function.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formulas I in which Z is a carbamate function, T is an amide function, and F is an ether function.
  • the substituted anionic compounds are characterized in that they are chosen from substituent compounds substituted by substituents of formula I in which Z is a carbamate function, T is an amide function, and F is an ester function.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula I in which Z is a carbamate function, T is an amide function, and F is a carbamate function.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula I in which Z is a carbamate function, T is an amide function, and F is an amide function.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted with substituents of formula I in which Z is a carbamate function, T is an ester function, and F is an ether function.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted with substituents of formulas I in which Z is a carbamate function, T is an ester function, and F is an ester function.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formulas I in which Z is a carbamate function, T is an ester function, and F is a carbamate function.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted by substituents of formulas I wherein Z is a carbamate function, T is an ester function, and F is an amide function.
  • the substituted anionic compounds are characterized in that they are selected from anionic compounds substituted with substituents of formula I wherein G is an ester function and Z is an ester function.
  • the substituted anionic compounds are characterized in that they are selected from anionic compounds substituted with substituents of formula I in which G is an amide function and Z is an ester function.
  • the substituted anionic compounds are characterized in that they are selected from anionic compounds substituted with substituents of formula I in which G is a carbamate function and Z is an ester function.
  • the substituted anionic compounds are characterized in that they are selected from anionic compounds substituted with substituents of formula I in which G is an ester function and Z is an amide function.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted by substituents of formula I in which G is an amide function and Z is an amide function.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted with substituents of formula I in which G is a carbamate function and Z is an amide function.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula I in which G is an ester function and Z is a carbamate function.
  • the substituted anionic compounds are characterized in that they are chosen from anionic compounds substituted with substituents of formula I in which G is an amide function and Z is a carbamate function.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted by substituents of formula I wherein G is a carbamate function and Z is a carbamate function.
  • the substituted anionic compounds are characterized in that they are selected from anionic compounds substituted with substituents of formula II in which G 'is an ester function and Z' is an ester function.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted by substituents of formula II in which G 'is an amide function and Z' is an ester function.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted by substituents of formula II in which G 'is a carbamate function and Z' is an ester function.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula II in which G 'is an ester function and Z' is an amide function.
  • the substituted anionic compounds are characterized in that they are chosen from substituted anionic compounds with substituents of formula II in which G 'is an amide function and Z' is an amide function.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted by substituents of formula II in which G 'is a carbamate function and Z' is an amide function.
  • the substituted anionic compounds are characterized in that they are chosen from anionic compounds substituted with substituents of formula II in which G 'is an ester function and Z' is a carbamate function.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula II in which G 'is an amide function and Z' is a carbamate function.
  • the substituted anionic compounds are characterized in that they are chosen from anionic compounds substituted with substituents of formula II wherein G 'is a carbamate function and Z' is a carbamate function.
  • the substituted anionic compounds are characterized in that they are chosen from substituted anionic compounds with substituents of formula I or II in which the radical -R 2 is a benzyl radical.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula I or II in which the radical -R 2 is derived from a hydrophobic alcohol.
  • the anionic compounds according to the invention are characterized in that the hydrophobic alcohol is chosen from alcohols consisting of an unsaturated and / or saturated, branched or unbranched alkyl chain, comprising 4 to 18 carbons.
  • the anionic compounds according to the invention are characterized in that the hydrophobic alcohol is chosen from alcohols consisting of an unsaturated and / or saturated, branched or unbranched alkyl chain comprising 6 to 18 carbons.
  • the anionic compounds according to the invention are characterized in that the hydrophobic alcohol is chosen from alcohols consisting of an unsaturated and / or saturated, branched or unbranched alkyl chain comprising 8 to 16 carbons.
  • the anionic compounds according to the invention are characterized in that the hydrophobic alcohol is octane !.
  • the anionic compounds according to the invention are characterized in that the hydrophobic alcohol is 2-ethylbutanol.
  • the anionic compounds according to the invention are characterized in that the hydrophobic alcohol is chosen from myristyl alcohol, cetyl alcohol, stearyl alcohol and cetearyl alcohol, butyl alcohol, oleyl alcohol.
  • the anionic compounds according to the invention are characterized in that the hydrophobic alcohol is chosen from the group consisting of cholesterol and its derivatives.
  • the anionic compounds according to the invention are characterized in that the hydrophobic alcohol is cholesterol.
  • the anionic compounds according to the invention are characterized in that the hydrophobic alcohol is chosen from menthol derivatives.
  • the anionic compounds according to the invention are characterized in that the hydrophobic alcohol is menthol in its racemic form. [000248] In one embodiment, the anionic compounds according to the invention are characterized in that the hydrophobic alcohol is the menthol isomer D.
  • the anionic compounds according to the invention are characterized in that the hydrophobic alcohol is the L-isomer of menthol.
  • the anionic compounds according to the invention are characterized in that the hydrophobic alcohol is chosen from tocopherols.
  • the anionic compounds according to the invention are characterized in that the tocopherol is alpha tocopherol.
  • the anionic compounds according to the invention are characterized in that the alpha tocopherol is the racemic alpha tocopherol.
  • the anionic compounds according to the invention are characterized in that tocopherol is the D isomer of alpha tocopherol.
  • the anionic compounds according to the invention are characterized in that the tocopherol is the L isomer of alpha tocopherol.
  • the anionic compounds according to the invention are characterized in that the hydrophobic alcohol is chosen from alcohols bearing an aryl group.
  • the anionic compounds according to the invention are characterized in that the aryl group-bearing alcohol is chosen from the group consisting of benzyl alcohol and phenethyl alcohol.
  • the substituted anionic compounds are characterized in that they are chosen from anionic compounds substituted with substituents of formula I or II in which the radical -R 2 is derived from a hydrophobic acid.
  • the anionic compounds according to the invention are characterized in that the hydrophobic acid is chosen from fatty acids.
  • the anionic compounds according to the invention are characterized in that the fatty acids are chosen from the group consisting of acids consisting of an unsaturated or saturated, branched or unbranched alkyl chain, comprising: from 6 to 30 carbons.
  • the anionic compounds according to the invention are characterized in that the fatty acids are chosen from the group consisting of linear fatty acids.
  • the anionic compounds according to the invention are characterized in that the linear fatty acids are chosen from the group consisting of caproic acid, oenanthic acid, caprylic acid, capric acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, acid ⁇ Mystic, stearic acid, arachidic acid, behenic acid, tricosanoic acid, lignoceric acid, heptacosanoic acid, octacosanoic acid and melissic acid.
  • the linear fatty acids are chosen from the group consisting of caproic acid, oenanthic acid, caprylic acid, capric acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, acid ⁇ Mystic, stearic acid, arachidic acid, behenic acid, tricosanoic acid, lignoceric acid, heptacosanoic acid,
  • the anionic compounds according to the invention are characterized in that the fatty acids are chosen from the group consisting of unsaturated fatty acids.
  • the anionic compounds according to the invention are characterized in that the saturated fatty acids are chosen from the group consisting of myristoleic acid, palmitoleic acid and oleic acid, elaidic acid, linoleic acid, alpha-linoleic acid, arachidonic acid, eicosapentaenoic acid, erucic acid and docosahexaenoic acid.
  • the anionic compounds according to the invention are characterized in that the fatty acids are chosen from the group consisting of bile acids and their derivatives.
  • the anionic compounds according to the invention are characterized in that the acids of the bile and their derivatives are selected from the group consisting of cholic acid, dehydrocholic acid, deoxycholic acid and chenodeoxycholic acid.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula II in which n is 0, the radical -Ri and the substituent - R'i, identical are carbon chains.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted with substituents of formula II in which n is 0, and the radical - [AA] - is an amino acid residue.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted with substituents of formula II in which n is equal to 0, the radical -Ri and the substituent - R'i, identical are carbon chains and the radical - [AA] - is a residue of phenylalanine.
  • the substituted anionic compounds are characterized in that they are chosen from substituted anionic compounds with substituents of formula II in which n is 0, the radical -R and the substituent - R identical are carbon chains linked to the backbone by an ether function and the radical - [AA] - is a residue of phenylalanine.
  • the substituted anionic compounds are characterized in that they are selected from His anionic substituted compounds of Formula II wherein substituents n is 0 f the -Ri- radical and the substituent - R'i, identical are carbon chains linked to the backbone by a carbamate function and the radical - [?] - is a residue of phenylalanine.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula II in which n is equal to 0, the radical -Ri and the substituent - R'i, identical are carbon chains linked to the backbone by an ether function and the radical - [AA] - is a residue of tryptophan.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula II in which n is equal to 0, the radical -R ⁇ - and the substituent - R'i, identical are carbon chains linked to the backbone by an ether function and the radical - [AA] - is a residue of leucine,
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula II in which n is 0, the radical -Ri - and the substituent - R'i, identical are carbon chains linked to the backbone by an ether function and the radical - [AA] - is a residue of alpha-phenylglycine.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted by substituents of formula II wherein n is 0, the radical -R 5 - and the substituent - R'i, identical are carbon chains linked to the backbone by an ether function and the radical - [AA] - is a residue of tyrosine.
  • the substituted anionic compounds are characterized in that they are chosen from substituted anionic compounds with substituents of formula II in which n and a are equal to 0,
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted by substituents of formula II in which n and a are equal to 0 and the radical - [AA] - is a phenylalanine residue directly linked to the backbone by a carbamate function.
  • the substituted anionic compounds are characterized in that they are chosen from anionic compounds substituted with substituents of formula I in which n is equal to 1, the radical -R 1 and the substituent - i, identical are carbon chains.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula I in which n is equal to 1, the radical -Ri and the substituent - R'i, identical are carbon chains and the radical - [Q] - is derived from a diamine.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula I in which n is equal to 1, the radical -R x - and the substituent - R'i, identical are carbon chains, the radical - [Q] - is derived from a diamine and the radical -R 2 is derived from a linear fatty acid.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula I in which n is equal to 1, the radical -R 1 and the substituent - R'i, identical are carbon chains linked to the backbone by an ether function, the radical - [Q] - is derived from a diamine and the radical -R 2 is derived from a linear fatty acid.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula I in which n is equal to 1, the radical -Rx- and the substituent - R'i, identical are carbon chains linked to the backbone by an ether function, the radical - [Q] - is derived from ethylenediamine and the radical -R 2 is derived from a linear fatty acid.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula I in which n is equal to 1, the radical -Ri and the substituent - R'i, identical are carbon chains linked to the backbone by an ether function, the radical - [Q] - is derived from ethylenediamine and the radical -R 2 is derived from dodecanoic acid.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted with substituents of formula I in which n is 1, the radical -Ri and the substituent - 'i, identical are carbon chains linked to the backbone by an ether function, the radical - [Q] - is derived from a diamine and the radical -R 2 is derived from a hydrophobic alcohol.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula I in which n is equal to 1, the radical - i - and the substituent - R'i, identical are carbon chains linked to the backbone by an ether function, the radical - [Q] - is derived from a diamine and the radical -R 2 is derived from cholesterol.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted with substituents of formula I in which n is equal to 1, the radical -Ri and the substituent - R'i, identical are carbon chains linked to the backbone by an ether function, the radical - [Q] - is derived from ethylenediamine and the radical -R 2 is derived from cholesterol.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted with substituents of formula I in which n is equal to 1, the radical -Ri and the substituent - R'i, identical are carbon chains, the radical - [Q] - is derived from an aminoalcohol and the radical -R 2 is derived from a linear fatty acid.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted with substituents of formula I wherein n is 1, the radical - r and the substituent - R i, identical are carbon chains linked to the backbone by an ether function, the radical - [Q] - is derived from an aminoalcohol and the radical -R 2 is derived from a linear fatty acid.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted with substituents of formula I in which n is equal to 1, the radical -Ri and the substituent - R'i, identical are carbon chains linked to the backbone by an ether function, the radical - [Q] - is derived from ethanolamine and the radical -R 2 is derived from a linear fatty acid.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula I in which n is equal to 1, the radical -Rr and the substituent -R , identical are carbon chains linked to the backbone by an ether function, the radical - [Q] - is derived from ethanolamine and the radical -R 2 is derived from dodecanoic acid.
  • the substituted anionic compounds are: characterized in that they are chosen from the anionic compounds substituted by substituents of formula II in which n is equal to 1, the radical -Ri and the substituent The same are carbon chains.
  • the substituted anionic compounds are: characterized in that they are chosen from the anionic compounds substituted with substituents of formula II in which n is equal to 1, the radical -R t - and the substituent - R'i, identical are carbon chains and the radical -R 2 is derived from an intial fatty acid.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted with substituents of formula II in which n is equal to 1, the radical -Ri and the substituent - R'i, identical are carbon chains linked to the backbone by an ether function and the radical -R 2 is derived from a linear fatty acid.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula II in which n is equal to 1, the radical -Ri ⁇ and the substituent - R'i, identical are carbon chains linked to the backbone by an ether function, the radical - [AA] - is a residue of lysine and the radical -R 2 is derived from a linear fatty acid.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted by substituents of formula II in which n is 1, the radical -Ri and the substituent - R'i, identical are carbon chains linked to the backbone by an ether function, the radical - [AA] - is a residue of lysine and the radical -R 2 is derived from dodecanoic acid.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted with substituents of formula II wherein n is 1, the radical -R x - and the substituent - R'i, identical are carbon chains and the radical -R 2 is derived from a hydrophobic alcohol.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula II in which n is equal to 1, the radical -Ri and the substituent - R'i, identical are carbon chains attached to the backbone by an ether function and the radical -R 2 is derived from a hydrophobic alcohol.
  • the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted with substituents of formula I wherein n is 1, the radical -Ri and the substituent - R'i, identical are carbon chains linked to the backbone by an ether function, the radical - [A] - is a residue of leucine and the radical -R 2 is derived from a hydrophobic alcohol,
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula II in which n is equal to 1, the radical - i - and the substituent - R'i, identical are carbon chains linked to the backbone by an ether function, the radical - [AA] - is a residue of leucine and the radical -R 2 is derived from cholesterol.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula II in which n is equal to 1, the radical -Ri and the substituent - R'i, identical are carbon chains linked to the backbone by an ether function, the radical - [AA] - is a residue of aspartic acid and the radical -R 2 is derived from the benzyialcohol,
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula II in which n is equal to 1, the radical -Ri and the substituent - R'i, identical are carbon chains linked to the backbone by an ether function, the radical - [AA] - is a residue of glycine and the radical -R 2 is derived from decanol.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula II in which n is equal to 1, the radical - i - and the substituent - R'i, identical are carbon chains linked to the backbone by an ether function, the radical - [A] - is a residue of phenyalanine and the radical -R 2 is derived from 3,7-dimethyloctanol.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula II in which n is equal to 1 and a is equal to 0. In one embodiment, the substituted anionic compounds are characterized in that they are selected from the anionic compounds substituted with substituents of formula II in which n is 1 and a is 0 and 2 is a carbon chain.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted with substituents of formula II in which n is equal to 1 and a is equal to 0, the radical - [AA] - is a residue of phenylalanine directly linked to the backbone by an amide function and R 2 is a carbon chain.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula II in which n is equal to 1 and a is equal to 0, the radical - [AA] - is a residue of phenylalanine directly linked to the backbone by an amide function and R 2 is derived from methanol.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula I in which n is equal to 2, the radical -Ri and the substituent - R'i, identical are carbon chains.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted with substituents of formula I in which n is equal to 2, the radical -R t - and the substituent - R'i, identical are carbon chains linked to the backbone by an ether function and the radical - [Q] - is derived from a diamine coupled to an amino acid.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula I in which n is equal to 2, the radical -Ri and the substituent - R'i, identical are carbon chains linked to the backbone by an ether function, the radical - [Q] - is derived from a diamine coupled to an amino acid and the radical R 2 is derived from a linear fatty acid.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted with substituents of formula I in which n is equal to 2, the radical -R and the substituent - R'i, identical are carbon chains, the radical - [Q] ⁇ is derived from ethylenediamine coupled to an amino acid and the radical R 2 is derived from a linear fatty acid.
  • the substituted anionic compounds are characterized in that they are chosen from the group consisting of substituents of formula I in which n is equal to 2, the radical -Ri and the substituent - R'i, identical are carbon chains linked to the backbone by an ether function, the radical - [Qj- is derived from ethylenediamine coupled to a lysine and the radical R 2 is derived from a linear fatty acid.
  • the substituted anionic compounds are characterized in that they are selected from anionic compounds substituted by substituents of the formula I wherein n is 2, ie 3 ⁇ 4 -Ri- radical and the substituent - R ' lf identical are carbon chains linked to the backbone by an ether function, the radical - [Q] - is derived from ethylenediamine coupled to a lysine and the radical R 2 is derived from dodecanoic acid,
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted with substituents of formula I in which n is equal to 2, the radical -Ri and the substituent - R'i, identical are carbon chains linked to the backbone by an ether function, the radical - [Q] - is derived from ethylenediamine coupled to a lysine and the radical R 2 is derived from decanoic acid,
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula I in which rs is equal to 2, the radical -Ri and the substituent - R'i, identical are carbon chains linked to the backbone by an ether function, the radical - [Q] - is derived from ethylenediamine coupled to a lysine and the radical R 2 is derived from octanoic acid.
  • the substituted anionic compounds are characterized in that they are chosen from anionic compounds substituted with substituents of formula II in which n is equal to 2, the radical -R x - and Substituting R'i, identical are carbon chains,
  • the substituted anionic compounds are characterized in that they are chosen from ionic compounds substituted with substituents of formula II wherein n is 2, the radical - i - and the substituent - R ' 1f are carbon chains linked to the backbone by an ether function and the radical - R 2 is derived from a hydrophobic alcohol.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula II in which n is equal to 2, the radical - i - and the substituent - R't, identical are carbon chains l backed to the backbone by an ether function, the radical - [AA] - is an aspartic acid residue and the radical -R 2 is derived from a hydrophobic alcohol.
  • the substituted anionic compounds are characterized in that they are selected from His anionic compounds substituted with substituents of formula II wherein n is 2, the radical -R, and the substituent - R'i, identical are carbon chains linked to the backbone by an ether function, the radical - [AA] - is an aspartic acid residue and the radical -R 2 is derived from dodecanoi,
  • the substituted anionic compounds are characterized in that they are selected from among its anionic compounds substituted with substituents of formula II in which n is 2, the radical -Ri and the substituent - R'i, identical are carbon chains linked to the backbone by an ester function and the radical -R 2 is derived from a hydrophobic alcohol,
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted by substituents of formula II in which n is equal to 2, the radical -R 1 - and the substituent - R 1, identical are carbon chains backed to the backbone by an ester function, the radical - [AA] - is an aspartic acid residue and the radical -R 2 is derived from a hydrophobic alcohol.
  • the substituted anionic compounds are characterized in that they are chosen from the anionic compounds substituted with substituents of formula H in which n is equal to 2, the radical -Ri and the substituent - R 1, identical are carbon chains backed to the backbone by an ester function, the radical - [AA] - is an aspartic acid residue and the radical - R 2 is derived from dodecanoi.
  • the anionic compound substituted in the isolated state carries a substituent of general formula I or II or V. In one embodiment, the substituted anionic compound in the isolated state carries two substituents of general formula I or II or V.
  • the substituted anionic compound in the isolated state carries three substituents of general formula I or II or V.
  • the substituted anionic compound in the isolated state carries four substituents of general formula I or II or V.
  • the anionic compound substituted in the isolated state carries five substituents of general formula I or II or V,
  • the substituted anionic compound in the isolated state carries six substituents of the general formula I or II or V.
  • the substituted anionic compound in the isolated state carries a substituent of general formula I or II or V per saccharide unit.
  • the substituted anionic compound in the isolated state carries two substituents of general formula I or II or V per saccharide unit.
  • the anionic compound substituted in the isolated state carries three substituents of general formula I or II or V per saccharide unit.
  • the substituted anionic compound in the isolated state carries four substituents of general formula I or II or V per saccharide unit.
  • the anionic compounds according to the invention are characterized in that at least one saccharide unit is in cyclic form.
  • the anionic compounds according to the invention are characterized in that at least one saccharide unit is in open reduced or open oxidized form.
  • the anionic compounds according to the invention are characterized in that at least one saccharide unit is chosen from the group of pentoses.
  • the anionic compounds according to the invention are characterized in that the pentoses are chosen from the group consisting of arabinose, ribulose, xylulose, lyxose, ribose and xylose. deoxyribose, arabitol, xylitol and ribitol.
  • the anionic compounds according to the invention are characterized in that at least one saccharide unit is chosen from the group of hexoses.
  • the anionic compounds according to the invention are characterized in that the hexoses are chosen from the group consisting of mannose, glucose, fructose, sorbose, tagatose, psicose and galactose. , allosis, altrose, talose, idose, gulose, fucose, fuculose, rhamnose, mannitol, xylitol, sorbitol and galactitol (dulcitol).
  • the hexoses are chosen from the group consisting of mannose, glucose, fructose, sorbose, tagatose, psicose and galactose. , allosis, altrose, talose, idose, gulose, fucose, fuculose, rhamnose, mannitol, xylitol, sorbitol and galactitol (dulcitol).
  • the anionic compounds according to the invention are characterized in that at least one saccharide unit is chosen from the group of uronic acids.
  • the anionic compounds according to the invention are characterized in that the uronic acids are chosen from the group consisting of glucuronic acid, iduronic acid, galacturonic acid, gluconic acid, mucic acid, glucaric acid and galactonic acid.
  • the anionic compounds according to the invention are characterized in that at least one saccharide unit is an N-acetylhexosamine.
  • the anionic compounds according to the invention are characterized in that the N-acetylhexosamine is chosen from the group consisting of N-acetylgalactosamine, N-acetylglucosamine and N-acetylmannosamine.
  • the anionic compounds according to the invention are characterized in that the saccharide unit is chosen from the group consisting of hexoses in cyclic form or in open form.
  • the anionic compounds according to the invention are characterized in that the saccharide unit is chosen from the group consisting of glucose, mannose, mannitol, xylitol or sorbitol.
  • the anionic compounds according to the invention are characterized in that the saccharide unit is chosen from the group consisting of fructose and arabinose.
  • the anionic compounds according to the invention are characterized in that the saccharide unit is N-acetylglucosamine.
  • the anionic compounds according to the invention are characterized in that the saccharide unit is N-acetylgalactosamine.
  • the anionic compounds according to the invention are characterized in that the saccharide unit is chosen from the group consisting of uronic acids.
  • the anionic compounds according to the invention are characterized in that the saccharide units are chosen from the group consisting of glucose, mannose, mannitol, xylitol or sorbitol. In one embodiment, the anionic compounds according to the invention are characterized in that the saccharide units are chosen from the group consisting of fructose and arabinose.
  • the anionic compounds according to the invention are characterized in that at least one of the saccharide units is N-acetylglucosamine.
  • the anionic compounds according to the invention are characterized in that at least one of the saccharide units is N-acetylgalactosamine.
  • the anionic compounds according to the invention are characterized in that the backbone is formed of a discrete number 2 ⁇ u ⁇ 8 of identical or different saccharide units.
  • the anionic compounds according to the invention are characterized in that the identical or different saccharide units, which make up the skeleton formed of a discrete number 2 ⁇ u ⁇ 8 of saccharide units, are selected from the group of pentoses in cyclic form and / or in open form.
  • the anionic compounds according to the invention are characterized in that the identical or different saccharide units, which make up the skeleton formed of a discrete number 2 ⁇ u ⁇ 8 of saccharide units, are selected from the group of hexoses in cyclic form and / or in open form.
  • the anionic compounds according to the invention are characterized in that the identical or different saccharide units, which make up the skeleton formed of a discrete number 2 ⁇ u ⁇ 8 of saccharide units, are selected from the group consisting of uronic acids in cyclic form and / or in open form.
  • the anionic compounds according to the invention are characterized in that the identical or different saccharide units, which make up the skeleton formed of a discrete number 2 ⁇ u ⁇ 8 of saccharide units, are chosen from the group of hexoses and pentoses.
  • the anionic compounds according to the invention are characterized in that the identical or different saccharide units, which make up the skeleton formed of a discrete number 2 ⁇ u ⁇ 8 of saccharide units, are chosen from the group of hexoses.
  • the anionic compounds according to the invention are characterized in that the two saccharide units are identical.
  • the anionic compounds according to the invention are characterized in that the two saccharide units are different.
  • the anionic compounds according to the invention are characterized in that the identical or different saccharide units are chosen from hexoses and / or pentoses and linked by a glycoside bond of the type (1,1). ).
  • the anionic compounds according to the invention are characterized in that the identical or different saccharide units are chosen from hexoses and / or pentoses and linked by a glycoside bond of the type (1,2). ).
  • the anionic compounds according to the invention are characterized in that the identical or different saccharide units are chosen from hexoses and / or pentoses and linked by a glycoside linkage of the type (1,3). ).
  • the anionic compounds according to the invention are characterized in that the identical or different saccharide units are chosen from hexoses and / or pentoses and linked by a glycoside bond of type (1,4). ).
  • the anionic compounds according to the invention are characterized in that the identical or different saccharide units are chosen from hexoses and / or pentoses and linked by a glycoside bond of type (1,6 ).
  • the anionic compounds according to the invention are characterized in that the backbone is formed of a discrete number 3 ⁇ u ⁇ 8 of identical or different saccharide units.
  • the anionic compounds according to the invention are characterized in that at least one of the same or different saccharide units, which make up the skeleton formed of a discrete number 3 ⁇ u ⁇ S d saccharide units, is selected from the group consisting of hexose and / or pentose units linked by identical or different glycoside bonds.
  • the anionic compounds according to the invention are characterized in that the identical or different saccharide units, which make up the skeleton formed of a discrete number 3 ⁇ u ⁇ 8 of saccharide units, are selected from hexoses and / or pentoses and linked by at least one glycoside bond of (1,2) type.
  • the anionic compounds according to the invention are characterized in that the identical or different saccharide units, which make up the skeleton formed of a discrete number 3 ⁇ u ⁇ 8 of saccharide units, are selected from hexoses and / or pentoses and linked by at least one glycoside linkage of (1,3) type.
  • the anionic compounds according to the invention are characterized in that the identical or different saccharide units, which make up the skeleton formed of a discrete number 3 ⁇ u ⁇ 8 of saccharide units, are selected from hexoses and / or pentoses and linked by at least one glycoside bond of (1,4) type.
  • the anionic compounds according to the invention are characterized in that the identical or different saccharide units, which make up the skeleton formed of a discrete number 3 ⁇ u ⁇ 8 of saccharide units, are selected from hexoses and / or pentoses and linked by at least one glycoside bond of (1,6) type.
  • the anionic compounds according to the invention are characterized in that they comprise at least one saccharide unit chosen from group consisting of hexoses in cyclic form and at least one saccharide unit selected from the group consisting of hexoses in open form.
  • the anionic compounds according to the invention are characterized in that the three saccharide units are identical.
  • the anionic compounds according to the invention are characterized in that two of the three saccharide units are identical.
  • the anionic compounds according to the invention are characterized in that the identical saccharide units are chosen from hexoses, two of which are in cyclic form and one in open reduced form and linked by glycosidic linkages. type (1,4).
  • the anionic compounds according to the invention are characterized in that the identical saccharide units are chosen from hexoses, two of which are in cyclic form and one in open reduced form and linked by glycosidic linkages. type (1.6).
  • the anionic compounds according to the invention are characterized in that the identical or different saccharide units are chosen from hexoses and that the central hexose is linked by a glycosidic bond of the following type:
  • the anionic compounds according to the invention are characterized in that the identical or different saccharide units are chosen from hexoses and that the central hexose is linked by a glycosidic bond of the following type:
  • the anionic compounds according to the invention are characterized in that the identical or different saccharide units are chosen from hexoses and that the central hexose is linked by a glycoside bond of the type (1, 2) and a glycoside bond of type (1,6).
  • the anionic compounds according to the invention are characterized in that the identical or different saccharide units are chosen from hexoses and that the central hexose is linked by a glycoside bond of the type (1, 2) and a glycoside linkage of (1,3) type.
  • the anionic compounds according to the invention are characterized in that the identical or different saccharide units are chosen from hexoses and that the central hexose is linked by a glycosidic bond of the following type:
  • the anionic compounds according to the invention are characterized in that the skeleton is erlose. In one embodiment, the anionic compounds according to the invention are characterized in that the three identical or different saccharide units are hexose units selected from the group consisting of mannose and glucose.
  • the anionic compound according to the invention is characterized in that the backbone is maltotriose.
  • the anionic compound according to the invention is characterized in that the backbone is isomaltotriose.
  • the anionic compounds according to the invention are characterized in that the four saccharide units are identical.
  • the anionic compounds according to the invention are characterized in that three of the four saccharide units are identical.
  • the anionic compounds according to the invention are characterized in that the four saccharide units are hexose units selected from the group consisting of mannose and glucose.
  • the anionic compound according to the invention is characterized in that the backbone is maltotetraose.
  • the anionic compounds according to the invention are characterized in that the identical or different saccharide units are chosen from hexoses and that a terminal hexose is linked by a glycoside bond of the type (1, 2) and that the others are linked together by a glycoside bond of type (1,6).
  • the anionic compounds according to the invention are characterized in that the identical or different saccharide units are chosen from hexoses and linked by a glycoside bond of (1,6) type.
  • the anionic compounds according to the invention are characterized in that the five saccharide units are identical.
  • the anionic compounds according to the invention are characterized in that the five saccharide units are hexose units selected from the group consisting of mannose and glucose. In one embodiment, the anionic compounds according to the invention are characterized in that the identical or different saccharide units are chosen from hexoses and linked by a glycoside bond of (1,4) type.
  • the anionic compound according to the invention is characterized in that the backbone is maltopentaose.
  • the anionic compounds according to the invention are characterized in that the six saccharide units are identical.
  • the anionic compounds according to the invention are characterized in that the identical or different saccharide units are chosen from hexoses and linked by a glycoside bond of (1,4) type.
  • the anionic compounds according to the invention are characterized in that the six identical or different saccharide units are hexose units selected from the group consisting of mannose and glucose.
  • the anionic compound according to the invention is characterized in that the backbone is maltohexaose.
  • the anionic compounds according to the invention are characterized in that the seven saccharide units are identical.
  • the anionic compounds according to the invention are characterized in that the identical or different saccharide units are chosen from hexoses and linked by a glycoside bond of (1,4) type.
  • the anionic compounds according to the invention are characterized in that the seven saccharide units are hexose units selected from the group consisting of mannose and glucose.
  • the anionic compound according to the invention is characterized in that the backbone is maltoheptaose.
  • the anionic compounds according to the invention are N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-oethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl
  • the anionic compounds according to the invention are N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-oethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl
  • the eight saccharide units are hexose units selected from the group consisting of mannose and glucose.
  • the anionic compound according to the invention is: characterized in that the skeleton is maltooctaose.
  • the anionic compound comprising a discrete number of saccharide units is a natural compound.
  • the anionic compound having a discrete number of saccharide units is a synthetic compound.
  • the anionic compounds according to the invention are: characterized in that they are obtained by enzymatic degradation of a polysaccharide followed by purification.
  • the anionic compounds according to the invention are: characterized in that they are obtained by chemical degradation of a polysaccharide followed by purification.
  • the anionic compounds according to the invention are characterized in that they are obtained chemically, by covalent coupling of 3 recursors of lower molecular weight.
  • the anionic compounds according to the invention are characterized in that the skeleton is sophorose.
  • the anionic compounds according to the invention are characterized in that they are chosen from anionic compounds whose backbone is sucrose.
  • the anionic compounds according to the invention are characterized in that they are chosen from anionic compounds whose skeleton is lactulose.
  • the anionic compounds according to the invention are characterized in that they are chosen from anionic compounds whose skeleton is maltulose.
  • the anionic compounds according to the invention are characterized in that they are chosen from anionic compounds whose skeleton is leucrose. In one embodiment, the anionic compounds according to the invention are characterized in that they are chosen from anionic compounds whose backbone is N-acetyl lactosamine.
  • the anionic compounds according to the invention are characterized in that they are chosen from anionic compounds whose backbone is N-acetylallolactosamine.
  • the anionic compounds according to the invention are characterized in that they are chosen from anionic compounds whose skeleton is rutinose.
  • the anionic compounds according to the invention are characterized in that they are chosen from anionic compounds whose backbone is isomaltulose.
  • the anionic compounds according to the invention are characterized in that they are chosen from anionic compounds whose backbone is fucosyllactose.
  • the anionic compounds according to the invention are characterized in that they are chosen from anionic compounds whose skeleton is gentianose.
  • the anionic compounds according to the invention are characterized in that they are chosen from anionic compounds whose backbone is raffinose.
  • the anionic compounds according to the invention are characterized in that they are chosen from anionic compounds whose skeleton is melezitose.
  • the anionic compounds according to the invention are characterized in that they are chosen from anionic compounds whose skeleton is panose.
  • the anionic compounds according to the invention are characterized in that they are chosen from anionic compounds whose skeleton is kestosis.
  • the anionic compounds according to the invention are characterized in that they are chosen from anionic compounds whose skeleton is stachyose.
  • the invention also relates to the processes for producing substituted anionic compounds, in the isolated state or in a mixture, chosen from anionic compounds substituted with substituents of formula I or II.
  • the substituted anionic compounds selected from the anionic compounds substituted with substituents of formula I or II are characterized in that they can be obtained by random grafting of the substituents on the saccharide backbone.
  • the substituted anionic compounds selected from the anionic compounds substituted with substituents of formula I or II are characterized in that they can be obtained by grafting substituents at precise positions on the saccharide units by a method implementing steps of protection / deprotection of the alcohol or carboxylic acid groups naturally carried by the backbone. This strategy leads to a selective grafting, in particular regioselective, of the substituents on the skeleton.
  • Protecting groups include, without limitation, those described in the work (Wuts, PGM et al., Greene's Protective Groups in Organic Synthesis 2007).
  • the saccharide backbone can be obtained by degradation of a high molecular weight polysaccharide.
  • the degradation pathways include, without imitation, chemical degradation and / or enzymatic degradation.
  • the saccharide backbone can also be obtained by forming glycosidic interactions between monosaccharide or oligosaccharide molecules by using a chemical or enzymatic coupling strategy.
  • the coupling strategies include those described in the publication (Smooth, JT et al., Advances in Carbohydrate Chemistry and Biochemistry 2009, 62, 162-236) and in the book (Lindhorst, TK, Essentials of Carbohydrate Chemistry and Biochemistry 2007, 157-209).
  • the coupling reactions can be carried out in solution or on solid support.
  • the saccharide molecules before coupling may carry substituents of interest and / or be functionalized when they are coupled together in a statistical or regioselective manner.
  • the compounds according to the invention can be obtained according to one of the following methods:
  • the compounds according to the invention isolated or in a mixture, can be separated and / or purified in various ways after obtaining them, in particular by the processes described above.
  • HPLC High performance liquid chromatography
  • RP-HPLH reverse phase HPLC
  • the invention also relates to the use of the anionic compounds according to the invention for the preparation of pharmaceutical compositions.
  • the invention also relates to a pharmaceutical composition
  • a pharmaceutical composition comprising one of the anionic compounds according to the invention as described above and at least one active ingredient.
  • the invention also relates to a pharmaceutical composition characterized in that the active ingredient is selected from the group consisting of proteins, glycoproteins, peptides and non-peptide therapeutic molecules.
  • Active ingredient means a product in the form of a single chemical entity and / or in the form of a combination having a physiological activity.
  • Said active ingredient may be exogenous, that is to say that it is provided by the composition according to the invention. It may also be endogenous, for example the growth factors that will be secreted in a wound during the first healing phase and that may be retained on said wound by the composition according to the invention.
  • the modes of administration are intravenous, subcutaneous, intradermal, transdermal, intramuscular, oral, nasal, vaginal, ocular, oral, pulmonary etc.
  • compositions according to the invention are either in liquid form, in aqueous solution, or in powder, implant or film form. They further comprise conventional pharmaceutical excipients well known to those skilled in the art.
  • compositions may advantageously comprise, in addition, excipients for formulating them in the form of gel, sponge, injectable solution, oral solution, lyoc etc.
  • the invention also relates to a pharmaceutical composition, characterized in that it is administrable as a stent, film or "coating" of implantable biomaterials, implant.
  • the mixture After heating for 1 h, the mixture is diluted with water, neutralized with acetic acid and then purified by ultrafiltration on a 1 kDa PES membrane against water.
  • the compound concentration of the final solution is determined by dry extract, then an acid / base assay in a 50/50 water / acetone (V / V) mixture is performed to determine the degree of methylcarboxylate substitution.
  • the degree of substitution in methylcarboxylate is 1.65 per glucosidic unit.
  • the solution of sodium maltotriosemethylcarboxylate is acidified on a Purolite resin (anionic) to obtain maltotriosemethylcarboxylic acid which is then lyophilized for 18 hours.
  • aqueous solution of imidazole (340 g / l) is added and the mixture is heated to 30 ° C.
  • the medium is diluted with water and then the solution obtained is purified by ultrafiltration on PES membrane of 1 kDa against 0.1N NaOH, NaCl 0.9% and water.
  • the compound concentration of the final solution is determined by dry extract.
  • a solution sample is freeze-dried and analyzed by 1H NMR in D20 to determine the degree of substitution of methylcarboxylates functionalized with phenylalanine.
  • the degree of substitution of methylcarboxylates functionalized with phenylalanine per glucoside unit is 0.65.
  • the degree of substitution of methylcarboxylates functionalized with phenylalanine per glucoside unit is 1.0.
  • the degree of substitution of methylcarboxylates of sodium sodi per glucoside unit is 0.65.
  • the degree of substitution of methylcarboxylate is 1.0 per glucosidic unit.
  • the solution of sodium maltotriosemethylcarboxylate is acidified on a Purolite resin (anionic) to obtain maltotriosemethylcarboxylic acid which is then lyophilized for 18 hours.
  • the degree of substitution of methylcarboxylates functionalized with phenylalanine per glucoside unit is 0.65.
  • the mixture is diluted with water and the resulting solution is purified by ultrafiltration on 1 kDa PES membrane against 0.9% NaCl, 0.01 N NaOH, and water.
  • the compound concentration of the final solution is determined by dry extract.
  • a solution sample is lyophilized and analyzed by 1 H NMR in D 2 0 to determine the degree of substitution of tryptophan-functional methylcarboxylates.
  • the degree of substitution with tryptophan functionalized methylcarboxylates per glucosidic unit is 1.0.
  • the degree of substitution of sodium methylcarboxylates per glucoside unit is 0.65.
  • Cholesteryl eugenate, paratoluenesulfonic acid salt is prepared from cholesterol and leucine according to the process described in US Pat. No. 4,826,818 (Kenji M., et al.).
  • the degree of substitution of methylcarboxylates grafted with cholesteryl leucinate per glucoside unit is 0.09.
  • the degree of substitution of sodium methylcarboxylates per glucoside unit is 1.56.
  • the solid is filtered and saponified in an OH / THF mixture to which 265 ml of 1N NaOH are added at room temperature.
  • the solution is stirred overnight at room temperature and then concentrated on an evaporation evaporator
  • the aqueous residue is acidified on a Purolite resin (anionic) to obtain mannitol N-methylcarboxylic acid
  • the compound concentration of the final solution determined by dry extract, then an acid / base assay in a water / acetone 50/50 (V / V) mixture is carried out to determine the degree of substitution in methylcarboxylate.
  • N-methylcarboxylic acid mannitol solution is then lyophilized for 18 hours.
  • the ethyl phenylalaninate solution is added and the mixture is stirred at 10 ° C.
  • An aqueous solution of midazole (340 g / L) is added.
  • the solution is then heated to 30 ° C and then diluted by adding water.
  • the solution obtained is purified by ultrafiltration on a 1 kDa PES membrane against 0.1N NaOH, 0.9% NaCl and water.
  • the compound concentration of the final solution is determined by dry extract.
  • a solution sample is lyophilized and analyzed by H-NMR in D 2 0 to determine the degree of substitution of phenylalanine functionalized N-methylcarboxylates.
  • the degree of substitution in functionalized N-methylcarboxylates by phenylalanine per molecule of mannitol is 0.35.
  • the degree of substitution of sodium N-methylcarboxylates per molecule of mannitol is 3.95.
  • the isocyanate of ethyl L-phenylalaninate is obtained according to the method described in the publication (Tsai, JH et al, Organic Syntheses 2004, 10, 544-545) from ethyl L-phenylalanine hydrochloride. (Bachem) and triphosgene (Sigma).
  • N-phenylalanine mannitol hexacarbamate acid is dissolved in water (50 g / l) and neutralized by gradual addition of ION sodium hydroxide to give an aqueous solution of sodium N-phenylalaninate mannitol hexacarbamate which is then lyophilized.
  • the degree of substitution of sodium methylcarboxylates per glucoside unit is 1.25.
  • the degree of substitution in methylcarboxylate is 1.45 per glucosidic unit.
  • the solution of sodium maitotriosemethylcarboxylate is acidified on a Purolite resin (anionic) to obtain maltotriosemethylcarboxylic acid which is then lyophilized for 18 hours.
  • the degree of substitution of sodium methylcarboxylates per glucosidic unit is 0.8.
  • the degree of substitution in sodium methylcarboxylate is 3.30.
  • the sodium maitotriosemethylcarboxylate solution is acidified on a Purolite (anionic) resin to obtain maltotriosemethylcarboxylic acid which is then lyophilized for 18 hours.
  • the degree of substitution of methylcarboxylates onctionnalised by phenylalanine per glucoside unit is 0.65.
  • the degree of substitution of sodium methylcarboxylates per glucoside unit is 2.65.
  • Lompose il MaitopentaosemetnyicarDoxyate oe sooium functionalized by L-phenyiaianine
  • the degree of substitution of sodium methylcarboxylates per glucoside unit is 1.0.
  • the degree of substitution of functionalized methylcarboxylates by phenylalanine per glucoside unit is 0.65.
  • the degree of substitution of sodium methylcarboxylates per glucoside unit is 1.0.
  • sodium maltotriosemethylcarboxylate characterized by a degree of substitution of sodium methylcarboxylate of 1.84, is functionalized by cholesteryl leucinate.
  • NMR 1 the degree of substitution of methylcarboxylates functionalized with cholesteryl leucinate is 0.08.
  • sodium maltotriosemethylcarboxylate characterized by a degree of substitution of sodium methylcarboxylate of 1.62, is functionalized by cholesteryl leucinate.
  • the degree of substitution of methylcarboxylates functionalized with cholesteryl leucinate is 0.29.
  • the degree of substitution of sodium methylcarboxylates per glucoside unit is 1.33.
  • sodium maltotriosemethylcarboxylate characterized by a degree of substitution of sodium methylcarboxylate of 3.30 is functionalized by cholesteryl leucinate.
  • the degree of substitution of methylcarboxylates functionalized with cholesteryl leucinate is 0.29.
  • the degree of substitution of sodium methylcarboxylates per glucoside unit is 3.01.
  • the degree of substitution of methylcarboxylates functionalized with cholesteryl leucinate is 0.14.
  • the degree of substitution of sodium methylcarboxylates per glucoside unit is 1, 11.
  • aqueous solution of midazole (340 g / L) is added after 90 minutes.
  • the medium is diluted with water and then the solution obtained is purified by ultrafiltration on a 1 kDa PES membrane against a NaHC0 3 / Na 2 CO 3 pH 10.4 150 mM, NaCl 0.9% and water .
  • the compound concentration of the final solution is determined by dry extract.
  • a solution sample is lyophilized and analyzed by RN 1 H in D 2 0 to determine the degree of substitution of methylcarboxylates functionalized with ⁇ -benzyl aspartate.
  • the degree of substitution of methylcarboxylates functionalized with ⁇ -benzyl aspartate per glucosidic unit is 0.53.
  • the dilauryl aspartate, paratoluenesulfonic acid salt is prepared from dodecanol and aspartic acid according to the process described in US Patent 4,826,818 (Kenji M., et al.).
  • sodium maltotriosemethylcarboxylate characterized by a degree of substitution of sodium methylcarboxylate of 2.73 is functionalized by dilauryl aspartate in DF.
  • the medium is diluted with water and the resulting solution is purified by dialysis on a cellulose membrane of 3.5 kDa against a NaHCO 3 / Na 2 CO 3 pH 10.4 150 m buffer, NaCl 0.9% and water.
  • the compound concentration of the final solution is determined by dry extract.
  • a sample solution is lyophilized and analyzed by NMR in D 2 X H 0 to determine the degree of substitution in chroniclylcarboxyiates functionalized aspartate dilauryl.
  • the degree of substitution of methylcarboxyiates functionalized with dilauryl aspartate is 0.36.
  • the degree of substitution of sodium methylcarboxyiates per glucoside unit is 2.37.
  • methyl ester of N, N-bis (dodecanoyl) lysine is obtained according to the process described in the publication (Pal, A et al., Tetrahedron 2007, 63, 7334-7348) from the methyl ester of the L-lysine, hydrochloric acid salt (Bachem) and dodecanoic acid (Sigma).
  • 2 - [(2-dodecanoylamino-6-dodecanoylamino) hexanoylamino] ethanamine is obtained according to the method described in US Pat. No. 2,387,201 (Weiner et al.) From the methyl ester of ⁇ , ⁇ -bis (dodecanoyl) lysine. and ethylenediamine (Roth).
  • a sodium maltotriosemethylcarboxylate characterized by a degree of substitution in sodium methylcarboxylate of 2.73 is functionalized by 2 - [(2-dodecanoylamino-6-jodecanoylamino) hexanoylamino] ethanamine.
  • NMR 1 the degree of substitution of methylcarboxylates functionalized with 2 - [(2-dodecanoylamino-6-jodecanoylamino) hexanoylamino] ethanamine is 0.21.
  • the degree of substitution of methylcarboxylates of sodiu m per glucoside unit is 2.52.
  • N- (2-aminoethyl) dodecanamide is obtained according to the process described in US Pat. No. 2,387,201 (Weiner et al.) From the methyl ester of dodecanoic acid [Sigma) and ethylenediamine ( Roth).
  • sodium maltotriosemethylcarboxylate characterized by a degree of substitution of sodium methylcarboxylate of 1.64 is functionalized by N- (2-3minoethyl) dodecanamide.
  • the degree of substitution of sodium methylcarboxylates per glucoside unit is 1.37.
  • the molar fraction of succinic ester formed per glucosidic unit is 2.77 by NMR ⁇ in D 2 0 / NaOD.
  • the solution of sodium maltotriosesuccinate is acidified on a Purolite resin (anionic) to obtain maltotriosuccinic acid which is then lyophilized for 18 hours.
  • a sodium maltotriose succinate characterized by a degree of substitution of sodium succinate of 2.77 is functionalized by dilauryl aspartate.
  • the degree of succinate substitution functionalized with dilauryl aspartate is 0.41.
  • the degree of substitution of sodium methylcarboxylates per glucoside unit is 2.36.
  • Decanoyl glycinate, paratoluenesulfonic acid salt is prepared from decanol and glycine according to the process described in US Pat. No. 4,826,818 (Kenji
  • sodium maltotriosemethylcarboxylate characterized by a degree of substitution of sodium methylcarboxylate of 1.64 is functionalized by decanoyl glycinate.
  • Cholesteryl 2-aminoethylcarbamate a hydrochloric acid salt, is prepared according to the process described in patent WO2010053140 (Akiyoshi, K et al.).
  • a sodium maltotriosemethylcarboxyate characterized by a degree of substitution of sodium methylcarboxylate of 2.73 is functionalized by cholesteryl 2-aminoethylcarbamate.
  • RM 1 the degree of substitution of methylcarboxylates functionalized with 2-aminoethylcarbamate cholesteryl is 0.28.
  • the degree of substitution of sodium methylcarboxylates per glucoside unit is 2.45.
  • sodium maltotriosemethylcarboxyate characterized by a degree of substitution of sodium methylcarboxylate of 1.64 is functionalized by alpha-phenylglycine.
  • the degree of substitution of methylcarboxylates functionalized with alpha-phenylglycine is 0.52.
  • the methyl ester of N, N-bis (octanoyl) lysine is obtained according to the method described in the publication (Pal, A et al., Tetrahedron 2007, 63, 7334-7348) from the methyl ester of the L-lysine, hydrochloric acid salt (Bachem) and octanoic acid (Sigma).
  • 2 - [(2-octanoylamino-6-octanoylamino) hexanoylamino] ethanamine is obtained according to the method described in US Pat. No. 2,387,201 (Weiner et al.) From the methyl ester of N, N-bis (octanoyl) lysine and ethylenediamine (Roth).
  • sodium maltotriosemethylcarboxyate characterized by a degree of substitution of sodium methylcarboxylate of 1.64, is functionalized by 2 - [(2-octanoylamino) -6- octanoylamino) hexanoylamino] ethanamine.
  • the degree of substitution of sodium methylcarboxylates per glucoside unit is 1.36.
  • hydrochloric acid salt (Bachem)
  • a sodium maltotriosemethylcarboxylate characterized by a degree of substitution of sodium methylcarboxylate of 1, 64 is functionalized by tyrosine.
  • the degree of substitution of methylcarboxylates functionalized with L-tyrosine is 0.81.
  • the degree of substitution of sodium methylcarboxylates per glucoside unit is 0.83.
  • sodium maltotriosemethylcarboxylate characterized by a degree of substitution of sodium methylcarboxylate of 1.64 is functionalized by 2-aminoethyl dodecanoate.
  • NMR 1 the degree of substitution of methylcarboxylates functionalized with 2-aminoethyl dodecanoate is 0.27.
  • a sodium tialtotriosemethylcarboxylate characterized by a degree of substitution of sodium 1,64-necylcarboxylate is functionalized with 3,7-dimethyloctanoyl phenylalaninate.
  • the degree of substitution of methylcarboxylates functionalized with 3,7-dimethyloctanoyl phenylalaninate is 0.39.
  • the degree of substitution of sodium methylcarboxylates per glucoside unit is 1.25.
  • a solution of sodium hyaluronate 4-mer (Contipro Biotech) at 30 g / L is acidified on a Purolite resin (anionic) to obtain an aqueous solution of nyaluronic acid whose pH is increased to 7.1 by addition an aqueous solution (40%) of tetrabutylammonium hydroxide (Sigma). The solution is then lyophilized for 18 hours.
  • the degree of substitution of functional carboxylates functionalized with methyl phenylalaninate per saccharide unit is 0.22.
  • Compound 32 Sodium maltotriosemethylcarboxylate functionalized with 2- [(2-decanoylamino-6-decanoylamino) hexanoylamino] ethanamine
  • Sodium tialtotriosemethylcarboxylate characterized by a degree of substitution of sodium methylcarboxylate of 1.64 is functionalized by 2 - [(2-decanoylamino-6-jecanoylamino) hexanoylamino] ethanamine.
  • the degree of substitution of sodium methylcarboxylates per glucoside unit is 1.43.
  • the ethyl ester of N-dodecanoyl-L-lysine, hydrochloric acid salt is prepared from dodecanoic acid (Sigma) and the ethyl ester of L-lysine, a salt of hydrochloric acid (Bachem) according to the method described in US4126628 [AM package).
  • a sodium maltotriosemethylcarboxylate characterized by a degree of substitution of sodium methylcarboxylate of 1.64, is functionalized by N-dodecanoyl-L-. lysine.
  • the degree of substitution of methylcarboxylates functionalized with ⁇ - ⁇ -dodecanoyl-L-lysine is 0.37.
  • the degree of substitution of sodium methylcarboxylates per glucoside unit is 1.27.
  • 1,6-ditriisopropylsilyl mannitol is obtained according to the method described in the publication (Bhaskar, V et al., Journal of Carbohydrate Chemistry 2003, 22 (9), 867-879).
  • a sodium dextranemethylcarboxylate functionalized with L-phenylalanine is synthesized from a dextran with a weight average molar mass of 1 kg / mol (Pharmacosmos, average degree of polymerization of 3.9) according to a process similar to that described in US Pat. described in the application WO2012153070.
  • the degree of substitution of sodium methylcarboxylates per glucoside unit is 1.0.
  • the degree of substitution in methylcarboxylates functionalized with L-phenylalanine per glucoside unit is 0.65.
  • a sodium dextranethylcarboxylate functionalized with L-phenylalanine is synthesized from a dextran with a weight average molar mass of 5 kg / mol (Pharmacosmos, average degree of polymerization of 19) according to a process similar to that described in US Pat. WO2010122385.
  • the degree of substitution of sodium methylcarboxylates per glucoside unit is 0.98.
  • the degree of substitution of methylcarboxylates functionalized with L-phenylalanine per glucoside unit is 0.66.
  • a sodium dextranemethylcarboxylate functionalized with cholesteryl Ieucinate is synthesized from a dextran with a weight average molar mass of 1 kg / mol (Pharmacosmos, average degree of polymerization of 3.9) according to a method similar to that described in the application WO2012153070.
  • the degree of substitution of sodium methylcarboxylates per glucoside unit is 1.64.
  • the degree of substitution of methylcarboxylates functionalized with cholesteryl leucinate per glucoside unit is 0.05.
  • a sodium dextranmethylcarboxylate functionalized with cholesteryl leucinate is synthesized from a dextran with a weight average molar mass of 5 kg / mol (Pharmacosmos, average degree of polymerization of 19) according to a method similar to that described in US Pat. WO2010041119.
  • the degree of substitution of sodium methylcarboxylates per glucoside unit is 1.60.
  • the lysozyme solution is finally added and the final mixture is homogenized on the roller stirrer for 1 minute.
  • the turbidity of the compound 1 / lyzozyme solution is analyzed compared with that of the counter-example Al / lyzozyme and counter-example A2 / lyzozyme solutions.
  • the turbidity of the compound 13 / lyzozyme solution is analyzed compared with that of the counter-example B1 / lyzozyme and counterexample B2 / lyzozyme solutions.
  • the results are shown in the following Table 4.
  • the turbidity of the compound 1 / lyzozyme solution is lower than that of the compound against-example Al / lyzozyme and compound against the A2 / lyzozyme counterexample, whatever the ratio.
  • the turbidity of the compound 13 / lyzozyme solution is lower than that of the compound against-example Bl / lyzozyme and compound against B2 / lyzozyme counterexample, whatever the ratio.
  • an interaction test with albumin has been performed.
  • the test carried out is a so-called fluorescence test with albumin, which makes it possible, by measuring the fluorescence variations of the albumin, to verify whether an interaction exists between the test compound and the albumin.
  • the compound / albumin solutions are prepared from stock solutions of serum albumin and compounds (BSA) by mixing the appropriate volumes to obtain a BSA concentration of 0.5 mg / mL and compound / BSA mass ratios of 1, 5 and 10. These solutions are prepared in PBS buffer at pH 7.4.
  • this ratio is less than 1, it means that the compound induces a partial extinction of the fluorescence of the albumin linked to a change of environment of the tryptophan residues. This change reflects an interaction between the compound and albumin. It has been verified in control that for all the compounds tested, the fluorescence of the compound alone is negligible compared to the fluorescence of albumin (fluorescence (compound) ⁇ 2% fluorescence (albumin)). The results are shown in Table 5.

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FR1260855A FR2997857B1 (fr) 2012-11-14 2012-11-14 Formulation a action rapide d'insuline comprenant un compose anionique substitue
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FR1351199A FR3001895B1 (fr) 2013-02-12 2013-02-12 Solution injectable a ph7 comprenant au moins une insuline basale dont le point isoelectrique est compris en 5,8 et 8,5 et un compose anionique porteur de charges carboxylates et de radicaux hydrophobes
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BR112014016889A8 (pt) 2012-01-09 2017-07-04 Adocia composição sob a forma de uma solução aquosa injetável, sujo ph está compreendido entre 6,0 e 8,0 e, formulação de dose unitária com ph compreendido entre 7 e 7,8
US20150314003A2 (en) 2012-08-09 2015-11-05 Adocia Injectable solution at ph 7 comprising at least one basal insulin the isoelectric point of which is between 5.8 and 8.5 and a hydrophobized anionic polymer
EP2919804B1 (de) 2012-11-13 2018-01-31 Adocia Schnell wirkende insulinformulierung mit einer anionischen substituierten verbindung
WO2018153506A1 (en) 2017-02-22 2018-08-30 Adocia Fast-acting insulin composition comprising a citric acid salt
BR112020011486A2 (pt) 2017-12-07 2020-11-17 Adocia Solução injetável de ph 7 compreendendo pelo menos uma insulina basal comum pi de 5,8 a 8,5 e um copoliaminoácido contendo cargas de carboxilato e radicais hidrofóbicos
CA3084688A1 (fr) 2017-12-07 2019-06-13 Adocia Solution injectable a ph 7 comprenant au moins une insuline basale dont le pi est compris entre 5,8 et 8,5 et un co-polyaminoacide porteur de charges carboxylates et de radicaux hydrophobes
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