# US 11,998,634 B2 · Micro- or nano emulsions including anticancer drugs > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,998,634 B2 - Document ID: US11998634B2 - Status: Granted - Kind: B2 - Application number: 17/414,065 - Filed: 2019-12-06 - Published: 2022-02-24 - Granted: 2024-06-04 - Earliest claimed: 2018-12-19 - Assignees: Capnopharm GmbH - Applicants: Capnopharm GmbH - Inventors: Ranjita Sahoo - Web page: https://patentgrep.com/patent/US11998634B2 ## CPC - A61K 9/107: Emulsions {; Emulsion preconcentrates; Micelles (composition of emulsions A61K47/00)} - A61K 9/1075: {Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers (A61K9/0026 takes precedence)} - A61K 9/0019: {Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner (non-active ingredients are additionally classified in A61K47/00)} - A61K 31/12: Ketones - A61K 31/282: Platinum compounds - A61K 31/337: having four-membered rings, e.g. taxol - A61K 31/704: attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin {(digitoxin A61K31/7048)} - A61K 33/243: Platinum; Compounds thereof - A61K 47/10: Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers - A61K 47/14: Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters - A61K 47/26: 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 - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) ## Abstract The invention relates to new emulsion formulations comprising polyethylene glycol (15)-hydroxystearate, polyglyceryl-3 oleate and one, two, three or more anti-cancer drugs as well as such emulsion formulations for use in the treatment of cancer and a method for producing such emulsion formulations. Preferably, the emulsion formulation can further comprise one or more immunomodulatory drugs or adjuvant. ## Claims ### Claim 1 An emulsion formulation comprising: (a) 1 to 15 wt. % of polyethylene glycol (15)-hydroxystearate, (b) 0.3 to 10 wt. % of polyglyceryl-3 oleate, (c) at least one anti-cancer drug selected from oxaliplatin, cisplatin, doxorubicin, or paclitaxel, (d) optionally, polysorbate, and (e) water, wherein the emulsion is an oil-in-water micro- or nanoemulsion and all percentages by weight are based on a total weight of the emulsion formulation. ### Claim 2 (depends on 1) The emulsion formulation according to claim 1, wherein (a) and (b) are in a weight ratio of 1:1 to 15:1 ((a):(b)). ### Claim 3 (depends on 1) The emulsion formulation according to claim 1, wherein the at least one anti-cancer drug is oxaliplatin in an amount of 0.005 to 1.5 wt. %, cisplatin in an amount of 0.001 to 1.5 wt. %, doxorubicin in an amount of 0.001 to 3.0 wt. %, paclitaxel in an amount of 0.00001 to 2 wt. %, or a combination thereof. ### Claim 4 (depends on 1) The emulsion formulation according to claim 1, wherein the average particle size of the oil-in-water emulsion is from 10 to 1000 nm. ### Claim 5 (depends on 1) The emulsion formulation according to claim 1, wherein the formulation is a liquid or an aerosol. ### Claim 6 (depends on 1) The emulsion formulation according to claim 1, wherein the formulation is prepared by or producible by a process comprising: providing the polyethylene glycol (15)-hydroxystearate, providing the polyglyceryl-3 oleate, providing the at least one anti-cancer drug, optionally, providing further components, adding the provided components to each other, and optionally, homogenising the provided compounds. ### Claim 7 (depends on 6) The emulsion formulation according to claim 6, wherein the homogenisation is performed: at 50 to 80° C., and/or by using low shear mixing, and/or by using medium shear mixing, and/or by using high shear mixing, and/or by using high pressure homogenisation. ### Claim 8 (depends on 1) A method for preparing the emulsion formulation of claim 1 comprising: providing polyethylene glycol (15)-hydroxystearate, providing polyglyceryl-3 oleate, providing the at least one anti-cancer drug, optionally, providing further components, adding the provided components to each other, and optionally, homogenising the provided compounds. ### Claim 9 (depends on 8) The method according to claim 8, wherein the homogenisation is performed: at 50 to 80° C., and/or by using low shear mixing, and/or by using medium shear mixing, and/or by using high shear mixing, and/or by using high pressure homogenisation. ### Claim 10 (depends on 8) The method according to claim 8, wherein the homogenising is performed simultaneously with the adding. ### Claim 11 (depends on 1) A method for treating cancer in a patient suffering from cancer comprising administering the emulsion formulation according to claim 1 to the patient. ### Claim 12 (depends on 11) The method of claim 11, wherein the emulsion formulation is administered to the patient by intraperitoneal administration. ### Claim 13 (depends on 12) The method of claim 12, wherein the emulsion formulation is administered using an assisting tool chosen from microneedles, spray devices, angioinjectors, or a combination thereof. ### Claim 14 (depends on 1) The emulsion formulation according to claim 1, wherein the polyethylene glycol (15)-hydroxystearate is in an amount of from 1 to 5 wt. % and the polyglyceryl-3 oleate is in an amount of 0.3 to 1 wt. %, based on the total weight of the formulation. ### Claim 15 (depends on 1) The emulsion formulation according to claim 1, wherein the weight ratio of (a) to (b) is 2:1 to 10:1 ((a):(b)). ### Claim 16 A method for treating cancer in a patient suffering from cancer comprising intraperitoneally administering to the patient an emulsion formulation comprising: (a) 1 to 15 wt. % of polyethylene glycol (15)-hydroxystearate, (b) 0.3 to 10 wt. % of polyglyceryl-3 oleate, (c) at least one anti-cancer drugs selected from oxaliplatin, cisplatin, doxorubicin, or paclitaxel, (d) optionally, polysorbate, and (e) water, wherein the emulsion is an oil-in-water micro- or nanoemulsion, the average particle size of the oil-in-water emulsion is from 10 to 1000 nm, and all percentages by weight are based on a total weight of the emulsion formulation. ### Claim 17 (depends on 16) The method of claim 16, wherein the emulsion formulation comprises oxaliplatin in an amount of 0.005 to 1.5 wt. %. ### Claim 18 (depends on 16) The method of claim 16, wherein the emulsion formulation comprises cisplatin in an amount of 0.001 to 1.5 wt. %. ### Claim 19 (depends on 16) The method of claim 16, wherein the emulsion formulation comprises doxorubicin in an amount of 0.001 to 3.0 wt. %. ### Claim 20 (depends on 16) The method of claim 16, wherein the emulsion formulation comprises paclitaxel in an amount of 0.00001 to 2 wt. %.