WO2021074403A1 - Kontrolliert freisetzende formulierungen stark lipophiler physiologisch aktiver substanzen - Google Patents

Kontrolliert freisetzende formulierungen stark lipophiler physiologisch aktiver substanzen Download PDF

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Publication number
WO2021074403A1
WO2021074403A1 PCT/EP2020/079248 EP2020079248W WO2021074403A1 WO 2021074403 A1 WO2021074403 A1 WO 2021074403A1 EP 2020079248 W EP2020079248 W EP 2020079248W WO 2021074403 A1 WO2021074403 A1 WO 2021074403A1
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WIPO (PCT)
Prior art keywords
dosage form
physiologically active
form according
active substances
highly lipophilic
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Ceased
Application number
PCT/EP2020/079248
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German (de)
English (en)
French (fr)
Inventor
Mirko Nowak
Jay Jesko NOWAK
Annette Grave
Monika Wentzlaff
Sarah Barthold
Christian Geugelin
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ADD Advanced Drug Delivery Technologies AG
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ADD Advanced Drug Delivery Technologies AG
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
Priority to AU2020365443A priority Critical patent/AU2020365443A1/en
Priority to CN202080072328.8A priority patent/CN114945353A/zh
Priority to CA3157654A priority patent/CA3157654A1/en
Priority to US17/769,424 priority patent/US20240139215A1/en
Priority to MX2022004523A priority patent/MX2022004523A/es
Priority to JP2022521684A priority patent/JP7778069B2/ja
Application filed by ADD Advanced Drug Delivery Technologies AG filed Critical ADD Advanced Drug Delivery Technologies AG
Priority to IL292018A priority patent/IL292018A/en
Priority to EP20800800.3A priority patent/EP4045014A1/de
Priority to BR112022006643A priority patent/BR112022006643A2/pt
Publication of WO2021074403A1 publication Critical patent/WO2021074403A1/de
Anticipated expiration legal-status Critical
Priority to JP2025169943A priority patent/JP2025182116A/ja
Ceased legal-status Critical Current

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    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
    • 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
    • A61K31/658—Medicinal preparations containing organic active ingredients o-phenolic cannabinoids, e.g. cannabidiol, cannabigerolic acid, cannabichromene or tetrahydrocannabinol
    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/167—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction with an outer layer or coating comprising drug; with chemically bound drugs or non-active substances on their surface
    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/167—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction with an outer layer or coating comprising drug; with chemically bound drugs or non-active substances on their surface
    • A61K9/1676—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction with an outer layer or coating comprising drug; with chemically bound drugs or non-active substances on their surface having a drug-free core with discrete complete coating layer containing drug
    • 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
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
    • 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
    • A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
    • A61K9/2806—Coating materials
    • A61K9/2813—Inorganic 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
    • A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
    • A61K9/2806—Coating materials
    • A61K9/2833—Organic macromolecular compounds
    • A61K9/286—Polysaccharides, e.g. gums; Cyclodextrin
    • A61K9/2866—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose

Definitions

  • the invention relates to formulations for highly lipophilic physiologically active substances, in particular formulations with controlled release, and to their production.
  • the highly lipophilic physiologically active substances are, for example, active pharmaceutical ingredients.
  • An example of highly lipophilic pharmaceutical active ingredients are cannabinoids.
  • a number of physiologically active substances have highly lipophilic properties, i.e. they have a relatively high log P, for example a log P of 4 or more, where the log P is the logarithm of the n-octanol / water partition coefficient.
  • formulations in particular oral formulations, with such physiologically active substances represents a particular challenge, in particular if a controlled release of the physiologically active substances is to be achieved.
  • the physiologically active substances with strong lipophilic properties include cannabinoids.
  • Cannabinoids are a heterogeneous group of pharmacologically active substances that have an affinity for the so-called cannabinoid receptors.
  • the cannabinoids include, for example, tetrahydrocannabinol (THC) and the non-psychoactive cannabidiol (CBD).
  • Cannabinoids have found considerable interest as drugs. There is evidence that cannabinoid administration can be beneficial in a number of clinical conditions, including pain, inflammation, epilepsy, sleep disorders, symptoms of multiple sclerosis, anorexia, and schizophrenia (N. Bruni et al., Cannabinoid Delivery Systems for Pain and Inflammation Treatment. Molecules 2018, 23, 2478). The provision of suitable dosage forms is associated with difficulties, however, since cannabinoids are highly lipophilic molecules (log P 6-7) with very low water solubility (2-10 pg / ml).
  • WO 2015/065179 A1 describes compressed tablets which, in addition to cannabidiol, contain lactose and sucrose fatty acid monoesters.
  • Dronabinol (A9-THC) is marketed in capsule form (Marinol ® ) and as an oral solution (Syndros ®). Marinol ® capsules are soft gelatine capsules that contain the active ingredient in sesame oil.
  • the finished drug Sativex ® which contains nabiximols, is an oral spray that is sprayed onto the inside of the cheek.
  • Epidiolex for the treatment of certain forms of epilepsy is made available in the form of an oral solution which, in addition to the active ingredient cannabidiol, contains the auxiliary substances absolute ethanol, sesame oil, strawberry aroma and sucralose.
  • One object of the invention is to provide solid dosage forms, in particular oral solid dosage forms, for highly lipophilic physiologically active substances such as Cannabinoids, which release the physiologically active substance (s) and which can be produced in a simple manner.
  • physiologically active substances such as Cannabinoids
  • This object is achieved by providing a solid dosage form which has a matrix with one or more highly lipophilic physiologically active substances; one or more water-soluble binders and not more than 20% by weight, based on the weight of all components, of further auxiliaries, a physiologically active substance being highly lipophilic if it has a log P of 4 or more.
  • solid forms of administration in particular oral solid forms of administration, of highly lipophilic physiologically active substances can be provided, the release being determined via the amount of water-soluble binder (s), based on the amount of strongly lipophilic substance / substances can be controlled.
  • the use of one or more water-soluble binders not only allows the formation of a matrix with the physiologically active substance (s), but also serves to control the release.
  • a water-soluble binder promotes the release of the highly lipophilic substances, which are only very slightly soluble in water. These are only released in sufficient quantity and speed by the binding agent.
  • Fig. 1 shows the in vitro release from three pellet products containing 2- [1R-3-methyl-6R- (1-methylethenyl) -2-cyclohexen-1-yl] -5-pentyl-1,3-benzenediol as Contains active ingredient and low viscosity hydroxypropylmethyl cellulose.
  • the dosage forms provided according to the invention contain one or more highly lipophilic physiologically active substances.
  • a substance is highly lipophilic if it has a log P of 4 or more.
  • the log P is the decadic logarithm of the n-octanol / water partition coefficient.
  • the distribution coefficient can be determined experimentally. Values typically refer to room temperature (25 ° C). The distribution coefficient can also be calculated approximately from the molecular structure.
  • the pellets according to the invention are particularly suitable for physiologically active substances with a log P of 5 or more and very particularly for those with a log P of 6 or more.
  • physiologically active substance refers to a substance that is administered to a human or an animal in order to develop an effect in the human or animal body.
  • the physiologically active substance can, for example, be a pharmaceutical active ingredient of a human or veterinary medicinal product or a food supplement.
  • An example of highly lipophilic pharmaceutical active ingredients that can be used according to the invention are cannabinoids.
  • the cannabinoids can be both phytocannabinoids and synthetic cannabinoids.
  • the phytocannabinoids are a group of about 70 terpenophenolic compounds (V.R. Preedy (Ed.), Handbook of Cannabis and Related Pathologies (1997)). These compounds typically contain a monoterpene residue attached to a phenolic ring and having a Cs-Cs alkyl chain that is in the meta position to the phenolic hydroxyl group.
  • a preferred group of cannabinoids are tetrahydrocannabinols of the following general formula (1): wherein R is selected from C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl or C 2 -C 20 -alkynyl and optionally has one or more substituents.
  • R is selected from C 1 -C 10 -alkyl or C 2 -C 10 -alkenyl and optionally has one or more substituents.
  • R in the formula (1) is an alkyl radical of the formula CsHu.
  • Compounds of the general formula (1) can exist in the form of stereoisomers.
  • the centers 6a and 10a preferably each have the R configuration.
  • the tetrahydrocannabinol is in particular A9-THC with the chemical name (6aR, 10aR) -6,6,9-trimethyl-3-pentyl-6a, 7,8, 10a-tetrahydro-6H-benzo [c] chromene-1-ol.
  • the structure is represented by the following formula (2):
  • cannabinoids are cannabidiols of the following general formula (3): wherein R is selected from Ci-C2o-alkyl, C2-C2o-alkenyl or C2-C2o-alkynyl and optionally has one or more substituents.
  • R is selected from C 1 -C 10 -alkyl or C 2 -C 10 -alkenyl and optionally has one or more substituents.
  • R in the formula (3) is an alkyl radical of the formula CsHu.
  • the cannabidiol is in particular 2- [1R-3-methyl-6R- (1-methylethenyl) -2-cyclohexen-1-yl] -5-pentyl-1,3-benzenediol.
  • A9-THC (6aR, 10aR) -6,6,9-trimethyl-3-pentyl-6a, 7,8,10a-tetrahydro-6H-benzo [c] chromene-1 -ol) and CBD (2- [1R-3-methyl-6R- (1-methylethenyl) -2-cyclohexen-1-yl] -5-pentyl-1,3-benzenediol) can be used.
  • cannabinoids are cannabinols of the following general formula (4): wherein R is selected from C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl or C 2 -C 20 -alkynyl and optionally has one or more substituents.
  • R is selected from C1-Cio-alkyl or C2-Cio-alkenyl and optionally has one or more substituents.
  • R in the formula (4) is an alkyl radical of the formula CsHu.
  • the cannabinol is in particular 6,6,9-trimethyl-3-pentyl-6 / - / - dibenzo [b, c] pyran-1-ol.
  • cannabinoids or cannabinoid mixtures from hemp extracts can also be used.
  • Nabiximols is a plant extract mixture used as a medicinal substance from the leaves and flowers of the hemp plant (Cannabis sativa L.) with standardized levels of tetrahydrocannabinol (THC) and cannabidiol (CBD).
  • THC tetrahydrocannabinol
  • CBD cannabidiol
  • Synthetic cannabinoids can also be used.
  • This includes 3- (1,1-dimethylheptyl) -6,6a, 7,8, 10, 10a-hexahydro-1-hydroxy-6,6-dimethyl- 9 / - / - dibenzo [ö, c (] pyran- 9-one.
  • This compound contains two stereogenic centers.
  • the drug nabilone is a 1: 1 mixture (racemate) of the (6aR, 10aR) form and the (6aS, 10aS) form.
  • Nabilone is a cannabinoid which is preferred according to the invention.
  • JWH-018 (1-naphthyl- (1-pentylindol-3-yl) methanone.
  • one or more highly lipophilic physiologically active substances such as one or more pharmaceutical active ingredients such as cannabinoids, are contained in a matrix.
  • the matrix preferably does not contain any further physiologically active substances.
  • the matrix contains one or more water-soluble binders.
  • These binders are polymeric film-forming substances.
  • suitable water-soluble binders are methyl cellulose (MC), hydroxypropylmethyl cellulose (HPMC), hydroxypropyl cellulose (HPC), hydroxyethyl cellulose (HEC), sodium carboxymethyl cellulose (Na-CMC) and polyvinylpyrrolidone (PVP).
  • HPMC Hydroxypropylmethylcellulose
  • low-viscosity HPMC such as HPMC with a viscosity of a 2% (w / w) aqueous solution at 20 ° C. of 6 mPa ⁇ s or less.
  • the matrix of one or more highly lipophilic physiologically active substances and one or more water-soluble binders can contain other customary auxiliaries, such as one or more fillers or carriers.
  • the amount of further auxiliaries is limited to not more than 20% by weight, based on the weight of all components. It preferably does not contain more than 10% by weight, based on the weight of all components, of further auxiliaries.
  • the matrix consists of strongly lipophilic physiologically active substance / strongly lipophilic physiologically active substances and binding agent (s), for example cannabinoid (s) and binding agent (s).
  • binding agent for example cannabinoid (s) and binding agent (s).
  • the matrix contains one or more water-soluble binders, based on the total amount of highly lipophilic physiologically active substances, in a total proportion of 0.1-10% by weight, preferably in a total proportion of 0.5-8% by weight and in particular contains in a total proportion of 1 - 6 wt .-%.
  • the release of the physiologically active substance can be adjusted by choosing the proportion in the specified ranges. For example, the release from an oral dosage form can be adjusted so that the physiologically active substance is released over the usual time of gastrointestinal passage.
  • the solid oral dosage form according to the invention which has a matrix with one or more highly lipophilic physiologically active substances, can be provided and used in any form.
  • the dosage form can be provided in the form of granules, matrix pellets or matrix tablets or contain one of these forms.
  • the production can take place in a manner known per se.
  • the dosage form contains matrix pellets.
  • the matrix pellets typically have a size in the range from 30 to 1800 ⁇ m, and the size can be determined by sieve analysis.
  • the matrix pellets can be used as an oral dosage form, e.g. being offered in sachets, or they can be further processed.
  • the matrix pellets can be provided with one or more additional coatings. This enables additional control of the release.
  • no coating is provided that controls the release.
  • the matrix pellets can also be used to obtain multiparticulate dosage forms. They can be filled into capsules or incorporated into tablets.
  • Matrix pellets with different release profiles can be combined in one dosage form (capsule / tablet / sachet).
  • the oral dosage forms according to the invention release the strongly lipophilic physiologically active substance contained therein or, if more than one strongly lipophilic physiologically active substance is contained, release all the strongly lipophilic physiologically active substances contained in the digestive tract after ingestion.
  • the dosage forms are used in particular for controlled release. In particular, they release more than 30% by weight and less than 80% by weight of the physiologically active substance contained within two hours. Furthermore, they release in particular more than 40% by weight and less than 90% by weight of the physiologically active substance contained within three hours. In addition, they release more than 50% by weight and less than 95% by weight of the physiologically active substance contained within four hours. If it contains more than one physiologically active substance, the information relates to all substances contained.
  • HPMC solution was then gradually added to the cannabidiol solution.
  • amorphous silica (Syloid ® 244 FP) was added.
  • the spray liquid obtained was sprayed onto starter cores made of microcrystalline cellulose (Cellets ® 500).
  • Example 1 pellet products The release from the results obtained in Example 1 pellet products is examined using a blade stirrer apparatus in 1000 ml phosphate buffer pH 6.8 with an addition of 0.4% Tween ® 80, namely at 37 ° C. The results obtained 1 are shown in Fig..

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  • Life Sciences & Earth Sciences (AREA)
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  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
PCT/EP2020/079248 2019-10-16 2020-10-16 Kontrolliert freisetzende formulierungen stark lipophiler physiologisch aktiver substanzen Ceased WO2021074403A1 (de)

Priority Applications (10)

Application Number Priority Date Filing Date Title
IL292018A IL292018A (en) 2019-10-16 2020-10-16 Formulations of highly lipophilic physiologically active substances with controlled release
CN202080072328.8A CN114945353A (zh) 2019-10-16 2020-10-16 高亲脂性生理活性物质的控释制剂
CA3157654A CA3157654A1 (en) 2019-10-16 2020-10-16 Controlled release formulations of highly lipophilic physiologically active substances
US17/769,424 US20240139215A1 (en) 2019-10-16 2020-10-16 Controlled release formulations of highly lipophilic physiologically active substances
MX2022004523A MX2022004523A (es) 2019-10-16 2020-10-16 Formulaciones de liberacion controlada para sustancias fisiologicamente activas altamente lipofilicas.
AU2020365443A AU2020365443A1 (en) 2019-10-16 2020-10-16 Controlled release formulations of highly lipophilic physiologically active substances
BR112022006643A BR112022006643A2 (pt) 2019-10-16 2020-10-16 Formulações de liberação controlada de substâncias fisiologicamente ativas altamente lipofílicas
JP2022521684A JP7778069B2 (ja) 2019-10-16 2020-10-16 高親油性生理活性物質の放出制御製剤
EP20800800.3A EP4045014A1 (de) 2019-10-16 2020-10-16 Kontrolliert freisetzende formulierungen stark lipophiler physiologisch aktiver substanzen
JP2025169943A JP2025182116A (ja) 2019-10-16 2025-10-08 高親油性生理活性物質の放出制御製剤

Applications Claiming Priority (2)

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EP19203580.6A EP3808341A1 (de) 2019-10-16 2019-10-16 Kontrolliert freisetzende formulierungen stark lipophiler physiologisch aktiver substanzen
EP19203580.6 2019-10-16

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US (1) US20240139215A1 (https=)
EP (2) EP3808341A1 (https=)
JP (2) JP7778069B2 (https=)
CN (1) CN114945353A (https=)
AU (1) AU2020365443A1 (https=)
BR (1) BR112022006643A2 (https=)
CA (1) CA3157654A1 (https=)
IL (1) IL292018A (https=)
MX (1) MX2022004523A (https=)
WO (1) WO2021074403A1 (https=)

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Publication number Priority date Publication date Assignee Title
EP3808336A1 (de) * 2019-10-16 2021-04-21 ADD Advanced Drug Delivery Technologies, Ltd. Kontrolliert freisetzende formulierungen stark lipophiler physiologisch aktiver substanzen
US20240317701A1 (en) 2020-12-17 2024-09-26 Nalu Bio, Inc. Synthesis of cannabidiol and analogs thereof, and related compounds, formulations, and methods of use
GB2618322A (en) * 2022-04-29 2023-11-08 113 Botanicals Ltd Compositions and methods

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EP3808341A1 (de) 2021-04-21
CA3157654A1 (en) 2021-04-22
JP2022553653A (ja) 2022-12-26
JP2025182116A (ja) 2025-12-11
US20240139215A1 (en) 2024-05-02
IL292018A (en) 2022-06-01
EP4045014A1 (de) 2022-08-24
BR112022006643A2 (pt) 2022-07-12
MX2022004523A (es) 2022-09-19
CN114945353A (zh) 2022-08-26
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