IP Library Granted Patent US 12,458,594
Granted Patent B2
US 12,458,594 · App. 16/630,456 · Granted Nov 4, 2025

Injectable water-in-oil emulsions and uses thereof

Inventors: Frédéric Deschamps (Paris, FR); Thierry De Baere (Chevilly Larue, FR); Lambros Tselikas (Charenton Le Pont, FR); Thomas Isoardo (Bourg-La-Reine, FR); Nicolas Huang (Paris, FR); Laurence Moine (Saint Cloud, FR); Nicolas Tsapis (Paris, FR); Elias Fattal (Paris, FR)
Assignees: Institut Gustave Roussy; Centre National de la Recherche Scientifique; Université Paris-Saclay
A61K9/107A61K31/4745A61K31/555A61K31/704A61K47/44B82Y5/00
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Quick Facts
Patent No.
US 12,458,594
App. No.
16/630,456
Granted
Nov 4, 2025
Kind
B2
Abstract

The present invention relates to a water-in-oil emulsion comprising a continuous oil phase and an aqueous phase dispersed in the form of drops, the said aqueous phase comprising polyester-based nanoparticles and at least one therapeutic agent.

Claims (17)

1 . A water-in-oil emulsion comprising:

(a) a continuous oily phase comprising a material selected from the group consisting of ethyl esters of iodized fatty acids from poppy seed oil, medium chain length (MCL) triglycerides having chain lengths between 8 and 12 carbon atoms, and squalene;

(b) an aqueous phase dispersed in the form of droplets, said aqueous phase comprising biodegradable solid polyester-based nanoparticles, said biodegradable solid polyester-based nanoparticles comprising a polyester selected from the group consisting of polylactic acid (polylactide), polyglycolic acid (polyglycolide), lactide-glycolide copolymers, poly (lactide-co-glycolide), lactide-glycolide-co-polyethylene glycol copolymers, polyorthoesters, polyanhydrides, polybutylacetone, polyvalerolactone, polymalic acid, polylactones, and mixtures thereof, said biodegradable solid polyester-based nanoparticles having a size between 100 nm and 300 nm; and

(c) at least one therapeutic agent encapsulated inside said droplets;

wherein the water-in-oil emulsion is a Pickering emulsion;

wherein the size of the droplets of the aqueous phase is between 10 μm and 100 μm;

wherein the biodegradable solid polyester-based nanoparticles form a physical barrier between the droplets encapsulating the therapeutic agent and the continuous oily phase in order to stabilize water-oil interface and

wherein said water-in-oil emulsion is stable for at least 24 hours.

2 . The water-in-oil emulsion according to claim 1 , wherein the continuous oily phase comprises squalene.

3 . The water-in-oil emulsion according to claim 1 , wherein the continuous oily phase comprises ethyl esters of iodized fatty acids from poppy seed.

4 . The water-in-oil emulsion according to claim 1 , in which the therapeutic agent is selected from the group consisting of immunomodulators, anticancer medicinal products, anti-angiogenic medicinal products, anti-infectious medicinal products, anti-inflammatory medicinal products, imaging contrast agents, radioactive agents, and infectious agents.

5 . The water-in-oil emulsion according to claim 4 , in which the anticancer medicinal product is selected from the group consisting of: an alkylating agent selected from the group consisting of cyclophosphamide, melphalan, ifosfamide, chlorambucil, busulfan, thiotepa, prednimustine, carmustine, lomustine, semustine, steptozotocin, decarbazine, temozolomide, procarbazine and hexamethylmelamine, a platinum derivative selected from the group consisting of cisplatin, carboplatin and oxaliplatin, cytotoxic antibiotic agents, antimicrotubule agents, anthracyclines, topoisomerase type I and II inhibitors, fluoropyrimidines, cytidine analogues, adenosine analogues, methotrexate, folinic acid, enzymes, antivascular agents, anti-angiogenic agents, antimitotic agents, kinase inhibitors, hormones, monoclonal antibodies, radioelements, oncolytic viruses, and mixtures thereof.

6 . The water-in-oil emulsion according to claim 1 , in which the therapeutic agent is an anticancer medicinal product selected from the group consisting of: doxorubicin, irinotecan, oxaliplatin, and mixtures thereof.

7 . The water-in-oil emulsion according to claim 1 , wherein the therapeutic agent is selected from the group consisting of anti-angiogenic monoclonal antibodies, anti-CTLA-4 monoclonal antibodies, anti-PD-1 monoclonal antibodies, anti-PD-L1 monoclonal antibodies, and mixtures thereof.

8 . The water-in-oil emulsion according to claim 1 , in which the polyester-based nanoparticles further comprise iron oxide particles.

9 . A medicinal product comprising the water-in-oil emulsion according to claim 1 .

10 . A pharmaceutical composition comprising the water-in-oil emulsion according to claim 1 , and at least one pharmaceutically acceptable excipient.

Assignments (2)
CHANGE OF ADDRESS Recorded Oct 21, 2022
From: UNIVERSITE PARIS-SACLAY
To: UNIVERSITE PARIS-SACLAY
Reel/Frame 061736/0969 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 3, 2020
From: DESCHAMPS, FREDERIC; DE BAERE, THIERRY; TSELIKAS, LAMBROS; ISOARDO, THOMAS; HUANG, NICOLAS; MOINE, LAURENCE; TSAPIS, NICOLAS; FATTAL, ELIAS
To: INSTITUT GUSTAVE ROUSSY; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE PARIS-SACLAY
Reel/Frame 051986/0815 →