Corning S.a.

Flamel Technologies

Corning Incorporated

Other

Flamel Ireland Limited

Corning Sas

Olivier Breyne

You-Ping Chan

Patrick Jean

Cécile Bonnet-Gonnet

Stéphanie Angot

Gérard Soula

Rémi Soula

Frédéric Checot

David Henry

Olivier Soula

Remi Meyrueix

Rémi Meyrueix

Rafael Jorda

Gauthier Pouliquen

Xavier Gerard Lafosse

Konstantine Bourchteine

Jean Patrick

Stephanie Angot

The present invention relates to a composition comprising at least one active ingredient with low aqueous solubility, said active ingredient being present therein in a form noncovalently associated with nanoparticles formed by at least one POM polymer of formula (I), and in which said active ingredient is present in a proportion of at least 5 &#x3bc;mol/g of POM. It is also directed towards the use of such nanoparticles, noncovalently associated with an active ingredient, with a view to increasing the aqueous solubilization of said active ingredient.

Composition comprising an active agent with low aqueous solubility

The present invention relates to novel biodegradable materials based on modified polyamino acids that are useful in particular in the vectorization of active principle(s) (APs). The invention is also directed to novel pharmaceutical, cosmetic, health-food or plant-protection compositions based on these polyamino acids. The aim of the invention is to provide a novel polymeric starting material which can be used for AP vectorization and which satisfy all the requirements: biocompatibility, biodegradability, ability to easily associate with or dissolve numerous active principles and to release these active principles in vivo. This goal is achieved by the present invention, which relates to novel polyglutamates modified by cationic groups, which, if they can be deprotonated, exhibit a pKa equal to or greater than 7, and by hydrophobic groups comprising from 8 to 30 carbon atoms. These polyglutamates modified by cationic groups are easily and economically converted into particles for the vectorization of active principles, these particles being themselves capable of forming stable aqueous colloidal suspensions. These modified polyglutamates exhibit the advantage of being less viscous than other analogous polymers while retaining an ability to associate proteins, such as insulin. Some are soluble in water at acidic pH and become insoluble at physiological pH (7.4) and should thus, during subcutaneous injection, precipitate on the site of injection.

Polyglutamic acids functionalized by cationic groups and hydrophobic groups and applications thereof, in particular therapeutic applications thereof

The present invention relates to novel particles comprising polyelectrolyte polymers which are transporters of active principle (AP), in particular protein and peptide active principle, and to novel modified-release pharmaceutical formulations comprising said AP microparticles. These novel particles loaded with AP release the AP over a prolonged period of time of several days, or even several weeks. The invention relates, in a first aspect, to particles comprising: The invention also relates to the process for the preparation of these particles, to a pharmaceutical formulation comprising such particles and to a process for the preparation of medicaments.

Modified-release particles of polyelectrolytes and pharmaceutical formulations thereof

The invention relates to novel biodegradable materials based on modified polyamino acids and suitable, in particular, for vectoring active substance(s) (AS). Said invention also relates to novel pharmaceutical, cosmetic, dietary or plant protective compositions which are based on said polyamino acids. The aim of said invention is to provide a novel polymer raw material usable for vectoring the AS and capable to optimally meet all specification in this area: biocompatibility, biodegradability, ability to become easily associated with many active substances or to solubilize them and to release said active substances in vivo. The aim is attained to 30 carbon atoms. Said polyglutamates modified by histidine derivatives are soluble with pH lower than 5 and are easily and economically convertible into active substance vectorization particles which are able to form stable aqueous colloidal suspensions. On the contrary, said modified polyglutamates are insoluble in water with a physiological pH (7.4), and thereby have to be precipitated on an injection site in the case of a subcutaneous injection.

Polyglutamic acids functionalised by histidine derivatives and hydrophobic groups and the uses thereof, in particular for therapeutic purposes

The present invention relates to pharmaceutical formulations for the release of an active principle (AP) over a sustained period of time. The invention relates to a liquid formulation comprising at least one active principle (AP) and an aqueous suspension based on colloidal particles of a polymer (PO), wherein said formulation satisfies the following four conditions: (a) the PO is a polyamino acid comprising glutamic residues, wherein some glutamic residues each carry a pendant cationic group (CG), said CG being identical or different from one another, and other glutamic residues each carry a pendent hydrophobic group (GH), said GH being identical or different from one another, (b) the pHf value of the pH of said formulation is between 3.0 and 6.5; (c) at the pHf value, the PO forms a colloidal solution which associates spontaneously and noncovalently with the AP; (d) 1 ml of said formulation precipitates during mixing with a volume of 1 ml of a test buffer solution Tp.

Self-precipitating pharmaceutical formulations for the modified release of an active principle

The invention relates to novel materials based on biodegradable polyamino acids, particularly useful for the vectorisation of active principals (PA). The invention further relates to novel, pharmaceutical, cosmetic, dietary or phytosanitary compositions. The invention provides novel polymeric raw material, for use in the vectorisation of PA and with an optimal match for all the requirements of the type: biocompatibility, biodegradability, stability, ability to easily associate with numerous active principals or to solubilise the same and to liberate said active principals in vivo. Said aim is achieved with polyamino acids comprising aspartic and/or glutamate units, some of which carry at least one graft, characterised in that at least one of said grafts is bonded to an aspartic or glutamate unit by means of an amino acids spacer based on Leu, and/or Ileu, and/or Val, and/or Phe and a hydrophobic group with C6-C30 is connected by an ester bond to the spacer.

Polyamino acids functionalised with at least one hydrophobic group and applications thereof particularly therapeutic applications

The invention concerns novel biodegradable polyaminoacid materials, useful in particular for vectoring active principle(s). The invention also concerns novel pharmaceutical, cosmetic dietetic or phytosanitary compositions based on said polyaminoacids. The invention aims at providing a novel polymer raw material, capable of being used for vectoring active principles and enabling optimal fulfillment of all specified requirements: biocompatibility, biodegradability, easy and inexpensive transformation into particles vectoring active principles, the particles being themselves capable of forming colloidal suspensions, of being easily associated with numerous active principles, and of releasing said active principles in vivo. Therefor, the present invention concerns first of all amphiphilic polyaminoacids comprising aspartic acid units and/or glutamic acid units, characterized in that at least part of said units carry grafts, including at least one alpha-tocopherol motif, for example (polyglutamate or polyaspartate grafted with alpha-tocopherol of synthetic or natural origin).

Polyaminoacids functionalized by alpha tocopherol and uses thereof, particular for therapeutic applications

The invention relates to novel materials based on biodegradable polyamino acids that are useful for vectorizing active principle(s)(AP). The aim of the invention is to supply a new polymeric raw material that is used for vectorizing AP and optimally fulfills all requirements concerning biocompatibility, biodegradability, the ability to be easily associated with numerous active principles or solubilize the active principles and to release the active principles in vivo. Such polymers can also be readily and economically transformed into particles vectorizing active principles according to the grafting rate of the hydrophobic groups, said particles being able to form stable aqueous colloidal suspensions. The aim of the invention is achieved by the inventive amphiphile polyamino acids comprising aspartic and/or glutamic units that carry grafts which encompass at least one hydrophobic unit and are linked to the aspartic and/or glutamic units via a rotula containing two amide functions, more particularly via a spacer of the lysine or ornithine type. The amide functions ensure better stability during hydrolysis than comparable products known in prior art. The invention also relates to new pharmaceutical, cosmetic, dietetic, or phytosanitary compositions based on the inventive polyamino acids.

Polyamino acids functionalized by at least one hydrophobic group and the therapeutic application thereof

The invention relates to novel materials based on biodegradable homopolyamino acids and which can be used for the vectorization of (an) active ingredient(s) (AI). The invention also relates to novel pharmaceutical, cosmetic, dietetic or phytosanitaty compositions based on homopolyamino acids. The invention can produce a novel polymer raw material which can be used for the vectoiization of Al that can optimally be: biocompatible, biodegradable, capable of becoming easily associated with a large number of active ingredients or solubilizing them and releasing the active ingredients in vivo. According to the present invention, which primarily relates to linear homopolyamino acids having aspartic or glutamic units and whose attachments can include hydrophobic groups having 8-30 carbon atoms. The homopolymers are amphiphilic and anionic and can easily be transformed at low cost into particles for the vectorization of active ingredients. The particles can form stable aqueous colloidal suspensions.

Telechelic homopolyamino acids functionalized with hydrophobic groups, and their applications, especially therapeutic applications

The present invention relates to novel compounds of the naphthopyran type which have an annelated carbocycle in position 5,6. These compounds are of formula (I) given below: in which A is an alicyclic ring which is optionally annelated with an aromatic ring and in which two adjacent Rcan together form at least one ring, for example a benzo group. These compounds (I) possess interesting photochromic properties. The invention also relates to the method of preparing these compounds (I), as well as their applications as photochromes and compositions and (co)polymer matrices comprising them.

Naphthopyrans annelated in C5-C6, their preparation and compositions and (CO)polymer matrices containing them

Disclosed are novel benzo-, naphtho- and phenanthrochromenes substituted by carbamated or ureated phenyls having the following general formula (I): wherein Rrepresents a group their preparation, photochromic compositions and articles containing them. This family of compounds have interesting and useful photochromic properties, especially in terms of absorption band and discoloration speed.

Benzo-, naphtho- and phenanthrochromene substituted by carbamated or ureated phenyls, preparation thereof and compositions and articles containing them

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Lyons, France

Olivier Breyne