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WO2025017072A1 - Compositions pharmaceutiques stables d'un inhibiteur de cyp11a1 - Google Patents

Compositions pharmaceutiques stables d'un inhibiteur de cyp11a1 Download PDF

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Publication number
WO2025017072A1
WO2025017072A1 PCT/EP2024/070275 EP2024070275W WO2025017072A1 WO 2025017072 A1 WO2025017072 A1 WO 2025017072A1 EP 2024070275 W EP2024070275 W EP 2024070275W WO 2025017072 A1 WO2025017072 A1 WO 2025017072A1
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WO
WIPO (PCT)
Prior art keywords
pharmaceutical composition
acid
pharmaceutically acceptable
composition according
per weight
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/EP2024/070275
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English (en)
Inventor
Kristo HAKALA
Jukka Salmia
Mayank Singhal
Elina TURUNEN
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.)
Orion Oyj
Original Assignee
Orion Oyj
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 Orion Oyj filed Critical Orion Oyj
Publication of WO2025017072A1 publication Critical patent/WO2025017072A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • 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
    • A61K9/2013—Organic compounds, e.g. phospholipids, fats
    • 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
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone

Definitions

  • the present invention relates to stable pharmaceutical compositions for oral administration, for example in the form of a tablet, pellets or powder suitable to be filled into a capsule shell, comprising 2-(isoindolin-2-ylmethyl)-5-((l-(methyl- sulfonyl)piperidin-4-yl)methoxy)-4H-pyran-4-one (I) or a pharmaceutically acceptable salt thereof as an active ingredient.
  • compositions of 2-(isoindolin-2-ylmethyl)-5-((l-(methylsulfonyl)piperidin-4- yl)methoxy)-4H-pyran-4-one (I) or pharmaceutically acceptable salts thereof, for example in the form of a tablet, pellets or powder suitable to be filled into a capsule shell, can be significantly improved by providing the composition with a stability enhancing amount of a pharmaceutically acceptable organic acid.
  • the present composition having improved chemical stability is particularly suitable as a dosage [0006] form for the treatment of patients suffering from hormonally regulated diseases where CYP11 Al inhibition is desired, such as prostate cancer and breast cancer.
  • the present disclosure provides a pharmaceutical composition
  • a pharmaceutical composition comprising 2-(isoindolin-2-ylmethyl)-5-((l-(methyl- sulfonyl)piperidin-4-yl)methoxy)-4H-pyran-4-one (I) or a pharmaceutically acceptable salt thereof as an active ingredient and a stability enhancing amount of a pharmaceutically acceptable organic acid.
  • the present disclosure relates to a pharmaceutical composition for oral administration, for example in the form of a tablet, pellets, or powder suitable to be filled into a capsule shell, comprising 2-(isoindolin-2-ylmethyl)-5-((l-(methyl- sulfonyl)piperidin-4-yl)methoxy)-4H-pyran-4-one (I) or a pharmaceutically acceptable salt thereof as an active ingredient.
  • the pharmaceutical composition is in the form of a tablet, such as direct compressed tablet, wet granulated tablet or dry granulated tablet.
  • Compound (I) or a pharmaceutically acceptable salt thereof may be in amorphous or crystalline state.
  • compound (I) is in the form of a pharmaceutically acceptable salt.
  • pharmaceutically acceptable salts of compound (I) are tosylate, napsylate, hydrobromic and benzylate salts.
  • a pharmaceutically acceptable salt of the present disclosure is a tosylate salt.
  • compositions comprising 2-(isoindolin-2-ylmethyl)-5-((l-(methylsulfonyl)piperidin- 4-yl)methoxy)-4H-pyran-4-one (I) or pharmaceutically acceptable salts thereof as an active ingredient can be significantly improved by providing the composition with a stability enhancing amount of a pharmaceutically acceptable organic acid.
  • the present disclosure provides a pharmaceutical composition
  • a pharmaceutical composition comprising 2-(isoindolin-2-ylmethyl)-5-((l-(methyl- sulfonyl)piperidin-4-yl)methoxy)-4H-pyran-4-one (I) or a pharmaceutically acceptable organic acid.
  • the present disclosure provides a composition comprising from about 0.1 % to about 15 %, for example from about 0.2 % to about 10 %, or from about 0.5 % to about 8 %, per weight of the composition, of a pharmaceutically acceptable organic acid.
  • the pharmaceutically acceptable organic acid has pKa of about 5 or lower. According to another embodiment, the pharmaceutically acceptable organic acid has pKa in the range of from about -3 to about 5.
  • the pharmaceutically acceptable organic acid is selected from the group consisting of citric acid, maleic acid, succinic acid, p-toluenesulfonic acid, tartaric acid, lactic acid, oxalic acid, malonic acid, glutaric acid, malic acid, adipic acid, gluconic acid, glutamic acid, glucuronic acid, fumaric acid, glycolic acid, ascorbic acid, aspartic acid, benzoic acid, and hyaluronic acid.
  • the pharmaceutically acceptable organic acid is citric acid or maleic acid.
  • a pharmaceutical composition which comprises from about 0.5 % to about 20 %, for example from about 1 % to about 15 %, or from about 2 % to about 10 %, per weight of the composition, of 2-(isoindolin-2-ylmethyl)-5-((l-(methylsulfonyl)piperidin-4- yl)methoxy)-4H-pyran-4-one (I) or a pharmaceutically acceptable salt thereof.
  • composition comprising a pharmaceutically acceptable salt of 2-(isoindolin-2-yl- methyl)-5-((l-(methylsulfonyl)piperidin-4-yl)methoxy)-4H-pyran-4-one (I) as an active ingredient.
  • composition comprising a tosylate salt of 2-(isoindolin-2-ylmethyl)-5-((l-(methylsulfonyl)- piperidin-4-yl)methoxy)-4H-pyran-4-one (I) as an active ingredient.
  • a pharmaceutical composition comprising from about 50 % to about 90 %, for example from about 60 % to about 88 %, or from about 70 % to about 85 %, per weight of the composition, of a filler.
  • a pharmaceutical composition comprising from about 0.5 % to about 10 %, for example from about 1 % to about 8 %, or from about 2 % to about 6 %, per weight of the composition, of a disintegrant.
  • a pharmaceutical composition comprising from about 0.5 % to about 15 %, for example from about 1 % to about 10 %, or from about 2 % to about 8 %, per weight of the composition, of a binder.
  • a pharmaceutical composition comprising from about 0.5 % to about 10 %, for example from about 0.8 % to about 8 %, or from about 1 % to about 5 %, per weight of the composition, of a lubricant.
  • compositions of the present disclosure can be, for example, in the form of a tablet, pellets, or powder suitable to be filled into a capsule shell.
  • powder refers to powdery material such as granules or milled powder.
  • the pharmaceutical composition is in the form of a tablet.
  • Tablets can be manufactured by the process of direct compression, wet granulation, or dry granulation (slugging or roller compaction).
  • Direct compression is regarded as a relatively quick process wherein the powdered materials included in the solid dosage form are compressed directly without modifying their physical nature.
  • the active ingredient, and other excipients, such as lubricant to prevent adhesion of the tablet material to the surface of the punches of the tablet press are blended in a blender or similar low shear apparatus before being compressed into tablets using a tablet press vehicle.
  • a direct compressed pharmaceutical composition comprising 2- (isoindolin-2-ylmethyl)-5-((l-(methylsulfonyl)piperidin-4-yl)methoxy)-4H-pyran-4- one (I) or a pharmaceutically acceptable salt thereof, a stability enhancing amount of a pharmaceutically acceptable organic acid, and optionally one or more other excipients.
  • the present disclosure provides a pharmaceutical composition
  • a pharmaceutical composition comprising a) from about 0.5 % to about 20 %, per weight of the composition, of 2- (isoindolin-2-ylmethyl)-5-((l-(methylsulfonyl)piperidin-4-yl)methoxy)-4H-pyran-4- one (I) or a pharmaceutically acceptable salt thereof; b) from about 0.1 % to about 15 %, per weight of the composition, of a pharmaceutically acceptable organic acid; c) from about 50 % to about 90 %, per weight of the composition, of a filler; d) from about 0.5 % to about 10 %, per weight of the composition, of a disintegrant; e) from about 0.5 % to about 15 %, per weight of the composition, of a binder; and f) from about 0.5 % to about 10 %, per weight of the composition, of a lubricant.
  • a pharmaceutical composition comprising a) from about 2 % to about 10 %, per weight of the composition, of 2- (isoindolin-2-ylmethyl)-5-((l-(methylsulfonyl)piperidin-4-yl)methoxy)-4H-pyran-4- one (I) or a pharmaceutically acceptable salt thereof; b) from about 0.5 % to about 8 %, per weight of the composition, of a pharmaceutically acceptable organic acid; c) from about 70 % to about 85 %, per weight of the composition, of a filler; d) from about 2 % to about 6 %, per weight of the composition, of a disintegrant; e) from about 2 % to about 8 %, per weight of the composition, of a binder; and f) from 1 % to about 5 %, per weight of the composition, of a lubricant.
  • Wet granulation typically comprises mixing the active ingredient and other intragranular components in a suitable mixer, granulating the mixture by spraying granulating liquid, for example water, into the mixture and drying the wet granules.
  • granulating liquid for example water
  • the composition also comprises extragranular components, they are suitably mixed with the dried granules, and, in case the composition is a tablet, the obtained mixture is compressed into tablets.
  • the obtained mixture can be filled directly into a capsule shell.
  • the stability enhancing pharmaceutically acceptable organic acid can be mixed as solid with intragranular components or dissolved in the granulating liquid.
  • a wet granulated pharmaceutical composition comprising 2-(isoindolin-2- ylmethyl)-5-((l-(methylsulfonyl)piperidin-4-yl)methoxy)-4H-pyran-4-one (I) or a pharmaceutically acceptable salt thereof, a stability enhancing amount of a pharmaceutically acceptable organic acid, and optionally one or more other excipients.
  • the wet granulated tablet comprises an intragranular part and an extragranular part.
  • the pharmaceutical composition comprises
  • compositions wherein the intragranular part comprises, from about 30 % to about 95 %, for example from about 50 % to about 90 % or from about 70 % to about 85 %, per weight of the composition.
  • a plasticizer such as polyethylene glycol (PEG) or glycerol, a film-forming agent such as hydroxypropylmethyl cellulose (HPMC), a colorant, such as ferric oxide or titanium dioxide, a glidant such as talc or magnesium stearate, and a flavouring agent such as polydextrose or sucrose, may be combined with a filmcoating liquid, preferably water, to result in a homogeneous coating suspension which is brought up, preferably sprayed, on the tablets in a suitable coating device, such as for example a perforated drum coater.
  • the film coating typically amounts to from about 2 % to about 5 %, for example from about 2.5 % to about 4 %, per weight of the tablet composition.
  • compositions comprising from about 0.1 mg to about 30 mg, for example from about 0.5 mg to about 25 mg, for example from about 1 mg to about 20 mg, for example from about 2 mg to about 10 mg, for example about 2.5 mg, about 3.5 mg, about 5 mg or about 7.1 mg, of 2-(isoindolin-2-ylmethyl)-5-((l-(methylsulfonyl)piperidin-4- yl)methoxy)-4H-pyran-4-one (I) or a pharmaceutically acceptable salt thereof, for example tosylate salt.
  • pKa refers to the common symbol used to express the strength of an acid and is related to the dissociation constant for the acid in aqueous solution.
  • pKa refers to the first pKa (pKal).
  • a “filler” refers to one or more pharmaceutically acceptable excipient(s) that adds bulkiness to a pharmaceutical composition.
  • fillers include sugars (e.g., mannitol or sucrose), starch, pregelatinized starch, microcrystalline cellulose, lactose, calcium hydrogen phosphate and sorbitol.
  • the filler is selected from mannitol, pregelatinized starch, microcrystalline cellulose, lactose, calcium hydrogen phosphate and a combination thereof.
  • the filler is selected from mannitol, pregelatinized starch, microcrystalline cellulose, and combinations thereof.
  • a “disintegranf ’ refers to one or more pharmaceutically acceptable excipient(s) which is added to the pharmaceutical composition to cause its disintegration to support the release of the active ingredient from the pharmaceutical composition.
  • disintegrants include croscarmellose sodium, cross-linked polyvinylpyrrolidone and sodium starch glycolate.
  • the disintegrant is selected from croscarmellose sodium, sodium starch glycolate and a combination thereof.
  • the disintegrant is croscarmellose sodium.
  • a “binder” refers to one or more pharmaceutically acceptable excipient(s) that imparts enhanced cohesion by binding the active ingredient and the excipients together in a mixture.
  • binders include hydroxypropylmethyl cellulose (HPMC), hydroxypropyl cellulose (HPC), polyvinylpyrrolidone (PVP), polyvinyl acetate and polyvinyl alcohol.
  • the binder is selected from hydroxypropylmethyl cellulose (HPMC), hydroxypropyl cellulose (HPC) and a combination thereof.
  • the binder is hydroxypropylmethyl cellulose (HPMC).
  • a “lubricant” refers to one or more pharmaceutically acceptable excipient(s), which is added to the pharmaceutical composition to reduce friction, heat, and wear when introduced between solid surfaces.
  • lubricants include sodium stearyl fumarate, magnesium stearate, talc, silica, calcium stearate and carnauba wax.
  • the lubricant is sodium stearyl fumarate.
  • compound of formula (I) or a pharmaceutically acceptable salt thereof, for example tosylate salt is suitably milled into the desired particle size.
  • the milled compound can have a particle size having the volume median diameter (Dv50) of not more than 50 pm, not more than 30 pm, or not more than 25 pm.
  • Dv50 may be in the range of 1 - 25 pm, between 2 - 20 pm, or between 5 - 15 pm.
  • the particle size distribution can be analyzed by laser light diffraction, for example using Beckman Coulter LS13320 laser diffraction particle size analyzer equipped with Tornado Dry Powder System using air as dispersion medium with measurement pressure 24”H2O ⁇ 2”H2O, sample amount 10 ml, system-controlled target 5 % for obscuration and applying Fraunhofer optical model.
  • Milling of the active ingredient can be carried out using suitable feeder and milling equipment, for example, single or twin screw/auger feeders, hammer mills, pin mills, jet mills or sieve mills, using suitable rotor speeds such as, for example 3000 - 10000 rpm. The milling can be conducted in a suitable temperature, for example, in room temperature or lower.
  • Compound of formula (I) or a pharmaceutically acceptable salt thereof is suitably administered, for example for the treatment of hormone dependent cancers, for example prostate cancer, in an amount ranging from about 0.5 mg to about 30 mg, or from about 1 mg to about 25 mg, for example from about 2 mg to about 15 mg, such as about 5 mg or about 7 mg per day to the patient.
  • the dose can be administered once daily or divided to several times a day, for example twice daily.
  • the invention is further illustrated by the following examples.
  • Example 1 Tablet composition (direct compressed)
  • Example 2 Tablet composition (direct compressed)
  • HPMC Hydroxypropyl methylcellulose
  • Citric acid 21.25 Citric acid 21.25
  • Example 3 Tablet composition (direct compressed)
  • HPMC Hydroxypropyl methylcellulose
  • Example 4 Tablet composition (direct compressed)
  • HPMC Hydroxypropyl methylcellulose
  • Example 5 Tablet composition (direct compressed)
  • Example 6 Tablet composition (direct compressed)
  • HPMC Hydroxypropyl methylcellulose
  • Example 7 Tablet composition (direct compressed)
  • HPMC Hydroxypropyl methylcellulose
  • HPMC Hydroxypropyl methylcellulose
  • Tablet compositions of Examples 1 to 8 were prepared by blending the components together and compressing the mixture into tablets with a tablet press.
  • Example 9 Tablet composition (wet granulated)
  • HPMC Hydroxypropyl methylcellulose
  • Example 10 Tablet composition (wet granulated)
  • HPMC Hydroxypropyl methylcellulose
  • the tablet compositions of Examples 9 and 10 were prepared by mixing the intragranular components in a high-shear mixer. The mixture was granulated by spraying water into the mixture. The granules were dried in a fluid-bed dryer and screened with a conical mill. Extragranular components were added, and the blend was compressed into tablets with a tablet press.
  • Example 11 Tablet composition (wet granulated, acid in granulation liquid)
  • HPMC Hydroxypropyl methylcellulose
  • Example 12 Tablet composition (wet granulated, acid in granulation liquid)
  • HPMC Hydroxypropyl methylcellulose
  • Example 13 Tablet composition (wet granulated, acid in granulation liquid)
  • HPMC Hydroxypropyl methylcellulose
  • Example 14 Tablet composition (wet granulated, acid in granulation liquid)
  • HPMC Hydroxypropyl methylcellulose
  • the tablet compositions of Examples 11 to 14 were prepared by mixing the intragranular components (excluding the acid) in a high-shear mixer.
  • the granulating liquid was prepared by dissolving the acid into water.
  • the mixture was granulated by spraying the granulating liquid into the mixture.
  • the granules were dried in a fluid-bed dryer and screened with a conical mill. Extragranular components were added, and the blend was compressed into tablets with a tablet press.
  • DC tablet compositions DC1 to DC 10 were prepared by blending the components together and compressing the mixture into tablets with a tablet press. The stability of the compositions was tested by storing the tablets in an open container in 60 °C / 75 % RH conditions for 4 weeks. The formulation descriptions and total amount of formed degradation impurities after 4 weeks are given in the Table 1. The quantitative compositions of the formulations are presented in Table 2 and Table 3. It can be seen that acid appeared to improve chemical stability of the direct compressed compositions.
  • API Active pharmaceutical ingredient (Compound (I), tosylate salt)
  • HPMC Hydroxypropylmethyl cellulose
  • MCC Microcrystalline cellulose
  • API Active pharmaceutical ingredient (Compound (I) tosylate salt)
  • HPMC Hydroxypropylmethyl cellulose
  • WG wet granulated tablets
  • WG wet granulated tablets
  • the stability of the compositions was tested by storing the tablets in a closed container in 40 °C / 75 % RH conditions for 6 months.
  • the formulation descriptions and total amount of formed degradation impurities after 6 months are given in the Table 4.
  • the actual compositions of the wet granulated (WG) formulations WG1 to WG3 are presented in Table 5. It can be seen that acid added as solid to the intragranular part appeared to improve chemical stability of the wet granulated (WG) compositions.
  • compositions WG4 to WG8 The stability of the compositions was tested by storing the tablets in a closed container in 40 °C / 75 % RH conditions for 6 months.
  • the formulation descriptions and total amount of formed degradation impurities after 6 months are given in the Table 6.
  • the actual compositions of the wet granulated (WG) formulations WG4 to WG8 are presented in Table 7. It can be seen that acid dissolved into the granulation liquid appeared to improve chemical stability of the wet granulated (WG) compositions.
  • API Active pharmaceutical ingredient (Compound (I) tosylate salt)
  • MCC Microcrystalline cellulose

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • Medicinal Preparation (AREA)

Abstract

La présente invention concerne une composition pharmaceutique destinée à être administrée par voie orale, par exemple sous la forme d'un comprimé ou d'une poudre apte à être introduite dans l'enveloppe d'une capsule, comprenant de la 2-(isoindoline-2-ylméthyl)-5-((1-(méthylsulfonyl)-pipéridine-4-yl)méthoxy)-4H-pyran-4-one (I) ou un de ses sels pharmaceutiquement acceptables en tant que principe actif. Le composé (I) ou un de ses sels pharmaceutiquement acceptables est un inhibiteur sélectif de l'enzyme CYP11A1 et est utile dans le traitement des maladies à régulation hormonale telles que le cancer, notamment le cancer de la prostate et le cancer du sein.
PCT/EP2024/070275 2023-07-19 2024-07-17 Compositions pharmaceutiques stables d'un inhibiteur de cyp11a1 Pending WO2025017072A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202363514501P 2023-07-19 2023-07-19
US63/514,501 2023-07-19

Publications (1)

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WO2025017072A1 true WO2025017072A1 (fr) 2025-01-23

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018115591A1 (fr) 2016-12-22 2018-06-28 Orion Corporation Dérivés de pyrane en tant qu'inhibiteurs de cyp11a1 (cytochrome p450 monooxygénase 11a1)
WO2022184978A1 (fr) * 2021-03-01 2022-09-09 Orion Corporation Nouvelles formes salines d'un inhibiteur de cyp11a1 à structure 4h-pyran-4-one

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018115591A1 (fr) 2016-12-22 2018-06-28 Orion Corporation Dérivés de pyrane en tant qu'inhibiteurs de cyp11a1 (cytochrome p450 monooxygénase 11a1)
WO2022184978A1 (fr) * 2021-03-01 2022-09-09 Orion Corporation Nouvelles formes salines d'un inhibiteur de cyp11a1 à structure 4h-pyran-4-one

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