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WO2025093812A1 - Formulation de dose imprimable - Google Patents

Formulation de dose imprimable Download PDF

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Publication number
WO2025093812A1
WO2025093812A1 PCT/FI2024/050568 FI2024050568W WO2025093812A1 WO 2025093812 A1 WO2025093812 A1 WO 2025093812A1 FI 2024050568 W FI2024050568 W FI 2024050568W WO 2025093812 A1 WO2025093812 A1 WO 2025093812A1
Authority
WO
WIPO (PCT)
Prior art keywords
printable
dose formulation
api
dose
solubilizers
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/FI2024/050568
Other languages
English (en)
Inventor
Julius LAHTINEN
Soumya VERMA
Sari AIRAKSINEN
Niko HASSINEN
Niklas Sandler
Farnaz SHOKRANEH
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Curifylabs Oy
Original Assignee
Curifylabs Oy
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Curifylabs Oy filed Critical Curifylabs Oy
Publication of WO2025093812A1 publication Critical patent/WO2025093812A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2095—Tabletting processes; Dosage units made by direct compression of powders or specially processed granules, by eliminating solvents, by melt-extrusion, by injection molding, by 3D printing
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/436—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having oxygen as a ring hetero atom, e.g. rapamycin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/4365—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system having sulfur as a ring hetero atom, e.g. ticlopidine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/554—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one sulfur as ring hetero atoms, e.g. clothiapine, diltiazem
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
    • A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
    • A61K31/585—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin containing lactone rings, e.g. oxandrolone, bufalin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/63—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide
    • A61K31/635—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide having a heterocyclic ring, e.g. sulfadiazine
    • 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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • 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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/2031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers
    • 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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
    • A61K9/2077—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C64/00—Additive manufacturing, i.e. manufacturing of three-dimensional [3D] objects by additive deposition, additive agglomeration or additive layering, e.g. by 3D printing, stereolithography or selective laser sintering
    • B29C64/10—Processes of additive manufacturing
    • B29C64/106—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B33—ADDITIVE MANUFACTURING TECHNOLOGY
    • B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
    • B33Y10/00—Processes of additive manufacturing
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B33—ADDITIVE MANUFACTURING TECHNOLOGY
    • B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
    • B33Y70/00—Materials specially adapted for additive manufacturing
    • B33Y70/10—Composites of different types of material, e.g. mixtures of ceramics and polymers or mixtures of metals and biomaterials

Definitions

  • the present disclosure relates to printable dose formulations comprising an active pharmaceutical ingredient and one or more solubilizers of hydrophilic-lipophilic balance (HLB) value of at least 8.
  • the disclosure also relates to methods for preparing medicament dosages using the printable dose formulations using 3D printers.
  • HLB hydrophilic-lipophilic balance
  • 3D printing enables pharmacists to create precise and accurate patient-tailored pharmacy preparations.
  • the 3D printing technology allows for the deposition of pharmaceutical materials very accurately, ensuring that each dose meets exact specifications. High level of precision minimizes the risk of dosing errors and enhances patient safety. 3D printing ensures consistent and reproducible results, eliminating batch-to-batch variations common in manual compounding.
  • the technology also facilitates stringent quality control measures, reducing the likelihood of contamination or inconsistencies in the final product.
  • a dose formulation to be printable by semisolid extrusion technology needs to be a homogenous paste, liquid or gel formed by solvents or heat and extrudable through a nozzle on a printing substrate such as on a blister package. This could be cumbersome in particular for formulations including active pharmaceutical ingredients (APIs) of low solubility. Also, the final pharmacy preparations must be easily removable from the printing substrate.
  • APIs active pharmaceutical ingredients
  • API active pharmaceutical ingredient
  • excipients include one or more solubilizers of hydrophilic-lipophilic balance value of at least 8, and wherein the printable dose formulation includes 0.1 - 10 wt.-% of said one or more solubilizers.
  • Figure 1 shows release (%) of an exemplary dose formulation including 2.5 wt-% prednisolone and 2.5 wt.-% polysorbate as a function of time. Dissolution was performed using USP II (paddle) apparatus. Media: 500 mL Milli Q water at 37 °C ⁇ 0.5 °C; number of samples analyzed: 4 tablets; paddle rpm:50.
  • the present disclosure concerns a printable dose formulation comprising
  • API active pharmaceutical ingredient
  • the excipients include one or more solubilizers of HLB value at least 8, preferably 8-18, more preferably 11-18, and wherein the printable dose formulation includes 0.1-10 wt.-%, preferably 0.25-5 wt.-%, such as 2.5-3 wt.-% of said one or more solubilizers.
  • solubilizer is an excipient used in dose formulations to assist solubility of poorly soluble drugs.
  • the dose formulations of the present disclosure include at least 40 wt.-% water, such as 40-50 wt.-% water. Contents of the solubilizers exceeding 10 wt.-% of the total mass of the formulation should be avoided since too high content could deteriorate printing properties of the dose formulation by significantly changing viscosity and/or density of the formulation.
  • the one or more solubilizers are preferably selected from polyethylene glycols, polysorbates, and polyoxyl stearate, more preferably from polyoxyl stearate and polysorbates, most preferably polysorbates.
  • Polysorbates are preferred since they have a well-defined safety limits for daily use.
  • solubilizers suitable for the present disclosure are listed in table 1 .
  • solubilizer ratio (w/w) in the formulation is preferably from 1 :2 to 1.3:1 , such as is 1 :1. These ratios ensure the formation of homogeneous dose formulations.
  • Exemplary APIs of BCS Class II suitable for the present disclosure are furosemide, hydrocortisone, spironolactone, hydrochlorothiazide, clopidogrel bisulfate, ramipril, quetiapine, tacrolimus, omeprazole, and prednisolone.
  • An exemplary APIs of BCS Class I suitable for the present disclosure are metoprolol, propranolol, and captopril.
  • the formulations were printed using a commercial 3D printer equipped with ink supply cartridges, heating elements, printheads (nozzle size 1.5 mm), control software, and a printing platform.
  • An exemplary base formulation used in the experiments i.e. a formulation including water but excluding the solubilizers of HLB value of at least 8 and the API is shown in Table 2. Table 2.
  • Prednisolone (1 wt.-%) was added to the formulation of table 2 with continuous mixing at 45 °C for 30 min. Homogenous admixture could not be obtained. Then the admixture was sonicated for 15 min in 45°C and mixed until seemingly homogenous. The formulation was printed on a plastic blister using the printing parameters shown above. The dose sticked and adhered on the blister. Examples
  • formulations including solubilizers were homogenous, and when printed, the printed dose did not adhere to the blister package.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Composite Materials (AREA)
  • Civil Engineering (AREA)
  • Ceramic Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Structural Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Inorganic Chemistry (AREA)
  • Medicinal Preparation (AREA)

Abstract

La présente divulgation concerne des formulations de dose imprimables comprenant un ingrédient pharmaceutique actif et des excipients comprenant un ou plusieurs tensioactifs d'équilibre hydrophile-lipophile (HLB) d'au moins 8. La divulgation concerne également une méthode de préparation de dosages de médicament à l'aide des formulations de dose imprimables.
PCT/FI2024/050568 2023-11-02 2024-10-22 Formulation de dose imprimable Pending WO2025093812A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FI20236217A FI20236217A1 (en) 2023-11-02 2023-11-02 Printable dosage form
FI20236217 2023-11-02

Publications (1)

Publication Number Publication Date
WO2025093812A1 true WO2025093812A1 (fr) 2025-05-08

Family

ID=93335144

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FI2024/050568 Pending WO2025093812A1 (fr) 2023-11-02 2024-10-22 Formulation de dose imprimable

Country Status (2)

Country Link
FI (1) FI20236217A1 (fr)
WO (1) WO2025093812A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108175930A (zh) * 2018-01-22 2018-06-19 中国人民解放军军事科学院军事医学研究院 一种3d打印的阴道给药装置
WO2019025857A2 (fr) * 2017-07-31 2019-02-07 Teva Pharmaceuticals Industries Limited Formes galéniques fonctionnelles fabriquées de manière additive
CN109394708B (zh) * 2017-08-17 2021-10-08 西安棣加生物科技有限公司 口腔速崩心脏病急救片及其3d打印方法、用途

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20170202811A1 (en) * 2016-01-20 2017-07-20 Zheng Wang Porous dosage compositions and methods of production
CN113599362A (zh) * 2021-01-15 2021-11-05 中国人民解放军军事科学院军事医学研究院 一种3d打印制剂及其制备方法和其应用
US11253481B1 (en) * 2021-07-12 2022-02-22 King Abdulaziz University Self-nanoemulsifying 3D-printed tablet composition and method of use thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019025857A2 (fr) * 2017-07-31 2019-02-07 Teva Pharmaceuticals Industries Limited Formes galéniques fonctionnelles fabriquées de manière additive
CN109394708B (zh) * 2017-08-17 2021-10-08 西安棣加生物科技有限公司 口腔速崩心脏病急救片及其3d打印方法、用途
CN108175930A (zh) * 2018-01-22 2018-06-19 中国人民解放军军事科学院军事医学研究院 一种3d打印的阴道给药装置

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
ALHIJJAJ MUQDAD ET AL: "An investigation into the use of polymer blends to improve the printability of and regulate drug release from pharmaceutical solid dispersions prepared via fused deposition modeling (FDM) 3D printing", EUROPEAN JOURNAL OF PHARMACEUTICS AND BIOPHARMACEUTICS, vol. 108, 1 November 2016 (2016-11-01), NL, pages 111 - 125, XP055909039, ISSN: 0939-6411, DOI: 10.1016/j.ejpb.2016.08.016 *

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