Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
  • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
  • C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
  • C08G69/10—Alpha-amino-carboxylic acids
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
  • A61K8/88—Polyamides
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
  • C08G69/48—Polymers modified by chemical after-treatment
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
  • A61K2800/57—Compounds covalently linked to a(n inert) carrier molecule, e.g. conjugates, pro-fragrances

Definitions

• polymers of the polylactic, polylactic-glycolic, polyoxyethylene-oxypropylene, polyamino acid or polysaccharide type are raw materials for manufacturing, for example, mass implants, microparticles, nanoparticles, vesicles, micelles or gels.
• these polymers must be suitable for the manufacture of such systems, they must also be biocompatible, non-toxic, non-immunogenic, economical and they must be easily removable. body and / or be biodegradable. On this last aspect, it is moreover essential that the biodegradation in the organism generates non-toxic products.
• the -X- binding motif of the hydrophobic graft (I) -X-GH-Y may also be described as a "spacer" or patella pattern, making it possible to connect the hydrophobic group GH to a main chain of the polyamino acid .
• -X- may comprise, eg at least one direct covalent bond and / or at least one amide bond and / or at least one ester bond.
• -X- may be a unit of the type belonging to the group comprising: the "amino acid” units different from the constituent monomeric unit of the polyamino acid, aminoalcohol derivatives, diamine derivatives, diol derivatives and hydroxy acid derivatives.
• the polyamino acid is characterized in that -X- and / or -Y is (are) free of residue (s) of alpha amino acid (s). More preferably still -X-, -GH- and -Y are free of alpha amino acids.
• the ionizable function (s) of Y capable of giving rise to at least one anionic charge is (are) chosen from the group of functions including: carboxylic / carboxylate function, sulfonic / sulfonate function, sulfuric / sulfate function and phosphoric / phosphate function.
• linear or branched C8 to C30 alkyls which may optionally comprise at least one unsaturation and / or at least one heteroatom,
• polyamino acids according to the invention correspond to the following general formula (II):
• cations based on residue (s) of amino acid (s) advantageously chosen from the class comprising cations based on lysine or arginine,
• hydrophobic grafts of formula (I): -X-GH-Y is, for example, chosen from the group comprising the following species:
• the polyamino acids of the invention are likely to be used in several ways depending on the nature of the hydrophobic groups and the degree of polymerization of the polyamino acid.
• Methods for shaping a polymer for the encapsulation of an active ingredient in the various forms contemplated by the invention are known to those skilled in the art.
• the polymers of the invention are for example obtained by methods known to those skilled in the art.
• the random polyamino acids can be obtained by grafting the hydrophobic graft formed by a -GH or a -GH-Y previously functionalized with a -X- bonding unit comprising for example at least one amino acid, directly on the polymer by a conventional reaction of coupling.
• the binding motif -X- may initially belong to the main chain of the polyamino acid.
• the block or mulitiblock polyamino acids can be obtained by sequential polymerization of the corresponding N-carboxyamino acid anhydrides (NCA).
• a polyamino acid, homopolyglutamate, homopolyaspartate or a block, multiblock, random or linear glutamate / aspartate copolymer is prepared by conventional methods.
• PA that may be associated with the polyamino acids according to the invention, whether or not in the form of (nano or micro) particles, mention may be made of: o proteins such as insulin, interferons, hormones growth, interleukins, erythropoietin or cytokines; peptides such as leuprolide or cyclosporine; o small molecules such as those belonging to the family of anthracyclines, taxoids or camptothecins; o and their mixtures.
• proteins such as insulin, interferons, hormones growth, interleukins, erythropoietin or cytokines
• peptides such as leuprolide or cyclosporine
• small molecules such as those belonging to the family of anthracyclines, taxoids or camptothecins
• o and their mixtures o proteins such as insulin, interferons, hormones growth, interleukins, erythropoietin or cytokines
• composition according to the invention is formulated so that it is capable of forming a deposit on the injection site.
• Medicaments in particular for oral, nasal, vaginal, ocular, subcutaneous, intravenous, intramuscular, intradermal, intraperitoneal or intracerebral administration, the active principles of these medicinal products being, in particular, proteins, glycoproteins, proteins bound to one or more polyalkylene glycol chains (for example PolyEthyleneGlycol (PEG), referred to as "PEGylated” proteins ⁇ , peptides, polysaccharides, liposaccharides, oligonucleotides, polynucleotides and hydrophobic, hydrophilic or amphiphilic organic small molecules;
• PEG PolyEthyleneGlycol
• the invention relates to a process for the preparation of: • medicaments, in particular for oral, nasal, vaginal, ocular, subcutaneous, intravenous, intramuscular, intradermal, intraperitoneal or intracerebral administration, the active principles these drugs can be, in particular, proteins, glycoproteins, proteins linked to one or more polyalkylene glycol chains (for example PolyEthyleneGlycol (PEG), so-called "PEGylated” proteins, peptides, polysaccharides, liposaccharides, hydrophobic, hydrophilic or amphiphilic oligonucleotides, polynucleotides and small organic molecules; • and / or nutrients;
• PEG PolyEthyleneGlycol
• aqueous solution containing a defined amount of polymer per milliliter at pH 7.4 and 200 IU insulin (7.4 mg) is prepared.
• the solutions are incubated for two hours at room temperature and free insulin is separated from the associated insulin by ultrafiltration (threshold at 100 KDa, 15 minutes under 10000G at 18 ° C).
• the free insulin recovered in the filtrate is then assayed by HPLC (High Performance Liquid Chromatography) and the amount of insulin associated is deduced.
• HPLC High Performance Liquid Chromatography

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• Health & Medical Sciences (AREA)
• Chemical & Material Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Animal Behavior & Ethology (AREA)
• General Health & Medical Sciences (AREA)
• Polymers & Plastics (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Medicinal Chemistry (AREA)
• Veterinary Medicine (AREA)
• Public Health (AREA)
• Birds (AREA)
• General Chemical & Material Sciences (AREA)
• Epidemiology (AREA)
• Dermatology (AREA)
• Medicinal Preparation (AREA)
• Polyamides (AREA)
• Cosmetics (AREA)
• Coloring Foods And Improving Nutritive Qualities (AREA)
• Materials For Medical Uses (AREA)
• Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

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Publications (1)

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• 2004
  • 2004-07-30 FR FR0408478A patent/FR2873704B1/fr not_active Expired - Fee Related
• 2005
  • 2005-07-25 DE DE602005017903T patent/DE602005017903D1/de not_active Expired - Lifetime
  • 2005-07-25 US US11/658,803 patent/US20100098656A1/en not_active Abandoned
  • 2005-07-25 CA CA002573612A patent/CA2573612A1/fr not_active Abandoned
  • 2005-07-25 WO PCT/FR2005/050610 patent/WO2006021710A1/fr not_active Ceased
  • 2005-07-25 AT AT05792029T patent/ATE449806T1/de not_active IP Right Cessation
  • 2005-07-25 EP EP05792029A patent/EP1773914B9/fr not_active Expired - Lifetime
  • 2005-07-25 JP JP2007523129A patent/JP5324093B2/ja not_active Expired - Fee Related

Patent Citations (2)

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