WO2021194280A1 - Nouvelle formulation pharmaceutique à stabilité améliorée contenant du taxane, un sel pharmaceutiquement acceptable de celui-ci, ou un hydrate de celui-ci - Google Patents

Nouvelle formulation pharmaceutique à stabilité améliorée contenant du taxane, un sel pharmaceutiquement acceptable de celui-ci, ou un hydrate de celui-ci Download PDF

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Publication number
WO2021194280A1
WO2021194280A1 PCT/KR2021/003717 KR2021003717W WO2021194280A1 WO 2021194280 A1 WO2021194280 A1 WO 2021194280A1 KR 2021003717 W KR2021003717 W KR 2021003717W WO 2021194280 A1 WO2021194280 A1 WO 2021194280A1
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pharmaceutical formulation
weight
taxane
polysorbate
formulation according
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PCT/KR2021/003717
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English (en)
Korean (ko)
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황금길
신동철
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보령제약 주식회사
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Publication of WO2021194280A1 publication Critical patent/WO2021194280A1/fr

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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
    • A61K9/08—Solutions
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
    • 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
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • 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
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12—Carboxylic acids; Salts or anhydrides thereof
    • 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
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/26—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
    • 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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • 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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • A61K9/0021—Intradermal administration, e.g. through microneedle arrays, needleless injectors
    • 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
    • A61K9/10—Dispersions; Emulsions
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Definitions

  • the present invention relates to a novel pharmaceutical formulation with improved stability comprising a taxane-based compound, a pharmaceutically acceptable salt thereof, or a hydrate thereof, and a method for preparing the same.
  • Taxanes are compounds extracted from the yew tree.
  • docetaxel (trade name: Taxotere)
  • paclitaxel (trade name: Taxol) extracted from the bark of Pacific yew (Taxus brevifolia) and leaves of European yew (Taxus baccata) are representative
  • a taxane-based anticancer agent exhibits anticancer effects by inhibiting depolymerization of microtubules by enhancing the assembly of intracellular microtubules and stabilizing their precursors.
  • taxane-based anticancer drugs such as docetaxel or paclitaxel are widely used in the treatment of various cancers, such as breast cancer, gastric cancer, non-cell lung cancer, ovarian cancer, and head and neck cancer.
  • taxane-based compounds such as docetaxel and paclitaxel are poorly water-soluble drugs with very low water solubility (water solubility about 0.003 mg/mL), and formulation is very difficult. Therefore, it cannot be formulated in the form of an aqueous solution for intravenous administration or the like.
  • taxane compounds such as docetaxel and paclitaxel are known to form various decomposition products, and even under controlled storage conditions, decomposition products are known to occur.
  • docetaxel is degraded under oxidative, thermal or basic conditions to generate various degradation products, ie, related substances, as shown in Table 1.
  • the inventors of the present invention have formulated a pharmaceutical formulation comprising a taxane compound, preferably docetaxel or paclitaxel, or a pharmaceutically acceptable salt thereof, or a hydrate thereof, as an active ingredient, a specific fatty acid
  • a pharmaceutical formulation comprising a taxane compound, preferably docetaxel or paclitaxel, or a pharmaceutically acceptable salt thereof, or a hydrate thereof, as an active ingredient, a specific fatty acid
  • An object of the present invention is to provide a pharmaceutical formulation containing a taxane-based compound as an active ingredient and having significantly improved stability and a method for preparing the same.
  • the present invention relates to a pharmaceutical formulation comprising a taxane-based compound as an active ingredient, a polysorbate-based surfactant having an oleic acid content of 70 to 85% by weight of the total fatty acid, particularly poly
  • An object of the present invention is to provide a pharmaceutical formulation comprising sorbate 80 and a method for preparing the same.
  • polysorbate 80 is characterized in that the content of oleic acid (oleic acid) in the total fatty acid is 70 to 85% by weight.
  • 1 is a view showing the degree of generation of related substances under accelerated conditions of a formulation containing docetaxel as an active ingredient according to the content of oleic acid in polysorbate 80;
  • FIG. 2 is a view showing the degree of generation of related substances under severe conditions of a formulation containing docetaxel as an active ingredient according to the content of oleic acid in polysorbate 80;
  • Figure 3 is a related substance under accelerated conditions of a formulation containing docetaxel as an active ingredient according to changing the content of oleic acid in the total fatty acids in polysorbate 80 to 70 to 90% by weight 6-oxo docetaxel (6-oxodocetaxel) It is a diagram showing the degree of occurrence.
  • the present invention comprises:
  • polysorbate 80 provides a pharmaceutical formulation, characterized in that the content of oleic acid (oleic acid) in the total fatty acid is 70 to 85% by weight.
  • the present invention is for cancer patients
  • polysorbate 80 relates to a method of administering a composition comprising a pharmaceutical formulation having an oleic acid content of 70 to 85% by weight of the total fatty acids.
  • the present invention provides (a) a taxane compound, a pharmaceutically acceptable salt thereof, or a hydrate thereof as an active ingredient;
  • composition for preparing a pharmaceutical formulation wherein the polysorbate 80 has an oleic acid content of 70 to 85% by weight in total fatty acids.
  • % by weight means “% by weight/weight (w/w)”.
  • the taxane-based compound cannot be sufficiently dissolved in the formulation because it does not properly exhibit the surfactant ability, and when the oleic acid content exceeds 85% by weight, related substances are generated A significant increase beyond this prediction significantly degrades the stability of the formulation.
  • polysorbate 80 included in the pharmaceutical formulation according to the present invention has a palmitic acid content of 2.5 to 20% by weight, preferably 3 to 18% by weight, and most preferably 4 to 16% by weight of the total fatty acids. It is characterized in that it is weight %.
  • the taxane compound included as an active ingredient in the pharmaceutical formulation according to the present invention is preferably docetaxel or paclitaxel, but is not limited thereto, and the trihydrate of docetaxel is most preferred.
  • the polyethylene glycol is characterized in that it is a mixture of PEG300 and PEG400.
  • PEG300 refers to polyethylene glycol having a molecular weight of 280 to 320
  • PEG400 refers to polyethylene glycol having a molecular weight of 380 to 420.
  • the polyethylene glycol contained in the pharmaceutical formulation according to the present invention is characterized in that it is a mixture of PEG300 and PEG400 as described above, and the polyethylene glycol mixture contains PEG300 and PEG400 in a weight ratio of 1:9 to 9:1, preferably 1:7 to 2:1, more preferably 1:5 to 1.5:1, most preferably 1:4 to 1:2.
  • the pharmaceutical formulation according to the present invention is characterized in that polysorbate 80 and polyethylene glycol are included in similar amounts.
  • polysorbate 80 and polyethylene glycol are included in similar amounts.
  • polysorbate 80 and polyethylene glycol in a weight ratio of 0.8:1.2 to 1.2:0.8, preferably 0.9:1.1 to 1.1:0.9, more preferably 0.95:1.05 to 1.05:0.95 included as a percentage of
  • polysorbate 80 and polyethylene glycol are included in similar amounts, the stability of the active ingredient in the pharmaceutical formulation can be further increased.
  • the pharmaceutical formulation according to the present invention may additionally contain a stabilizing agent.
  • the stabilizer according to the present invention is preferably an organic acid, but is not limited thereto, and more preferably citric acid or a hydrate thereof.
  • an active ingredient in the pharmaceutical formulation according to the present invention, is 5 to 50 mg, preferably 10 to 30 mg, more preferably 15, based on the weight of the taxane-based compound. to 25 mg may be included.
  • a pharmaceutically acceptable salt or a hydrate thereof is 5 to 50 mg, preferably 10 to 30 mg, more preferably 15, based on the weight of the taxane-based compound. to 25 mg may be included.
  • 21.34 mg of docetaxel trihydrate is included, 20 mg of docetaxel is included in the pharmaceutical formulation according to the present invention.
  • the pharmaceutical formulation according to the present invention contains 250 to 850 mg of polysorbate 80, preferably 350 to 700 mg, more preferably 480 to 600 mg, and 250 to 850 mg of polyethylene glycol, preferably 350 to 700 mg, more preferably 480 to 600 mg.
  • the polyethylene glycol is a mixture of PEG300 having a molecular weight of 280 to 320 and PEG400 having a molecular weight of 380 to 420, and the content of PEG300 in the mixture is 65 to 225 mg, preferably 90 to 185 mg, more preferably 120 to 160 mg. and the content of PEG400 is 185 to 625 mg, preferably 260 to 515 mg, more preferably 360 to 440 mg.
  • the pharmaceutical formulation according to the present invention contains 1.0 to 3.0% by weight of a taxane compound, a pharmaceutically acceptable salt or hydrate thereof, 24.0 to 73.0% by weight of polysorbate 80, and 24.0% by weight of polyethylene glycol, based on the total weight of the formulation. to 73.0% by weight,
  • a taxane-based compound, a pharmaceutically acceptable salt thereof or a hydrate thereof is 1.3 to 2.5 wt%
  • polysorbate 80 is 34.0 to 63.0 wt%
  • polyethylene glycol is 34.0 to 63.0 wt%
  • a taxane-based compound More preferably, it contains 1.7 to 2.1% by weight of a taxane-based compound, a pharmaceutically acceptable salt or hydrate thereof, 44.0 to 54.0% by weight of polysorbate 80, and 44.0 to 54.0% by weight of polyethylene glycol. .
  • the organic acid used as a stabilizer preferably citric anhydride
  • the organic acid used as a stabilizer is included in 1 to 10 mg, preferably 3 to 7 mg, and more preferably 4 to 6 mg, in the total formulation, in a weight ratio in the entire pharmaceutical formulation according to the present invention. 0.1 to 1.0% by weight, preferably 0.2 to 0.8% by weight, more preferably 0.3 to 0.6% by weight.
  • the pharmaceutical formulation according to the present invention may be administered in the form of an injection to a patient in need of treatment in the form of intravenous administration, intramuscular administration or subcutaneous administration, but is not limited thereto.
  • the pharmaceutical formulation according to the present invention may be provided in the form of a pre-filled syringe in a form stored in a glass ampoule or plastic container for administration, or a ready-to-injection form.
  • the present invention is not limited thereto, and may be administered after appropriate dilution using an appropriate solution, for example, physiological saline or glucose injection, if necessary.
  • the present invention relates to the use of a pharmaceutical formulation containing the taxane compound according to the present invention as an active ingredient for the treatment of cancer or tumor, and administering the pharmaceutical formulation according to the present invention to a patient in need of the treatment. It relates to a method of treatment for cancer characterized.
  • the type of cancer that can be treated with the pharmaceutical formulation according to the present invention is not particularly limited, and breast cancer, stomach cancer, lung cancer, ovarian cancer, head and neck cancer, colorectal cancer, prostate cancer, pancreatic cancer, skin cancer, blood cancer, esophageal cancer, liver cancer, etc. may be selected, but is not limited thereto.
  • the pharmaceutical formulation according to the present invention can be used for treatment in combination with other anticancer agents.
  • the anticancer agent that can be used in combination with the pharmaceutical formulation according to the present invention is not particularly limited, and small molecule compounds, antibodies, antibody-drug conjugates, aptamers, protein toxins, radioactive elements, RNAi (RNA interference), CAR (Chimeric antigen receptor) -T cells and CAR-NK (Natural killer cell) cells, etc. may be selected, but not limited thereto, and the antibody is particularly preferably an immune checkpoint inhibitor, an antibody for targeted therapy, and the like, but is not limited thereto.
  • Example 1 Stability of formulation according to oleic acid content in polysorbate 80
  • formulation (b) having an oleic acid content of 87.2% by weight and 99.3% by weight of formulation (a) compared to the total fatty acid under accelerated conditions
  • formulations (c) and formulations (d) which are 76.5 wt% and 69.8 wt%, respectively
  • the total related substance generation increases rapidly after 2 weeks, and in particular, it can be seen that the generation amount of 6-oxo docetaxel is significantly increased.
  • Example 2 Stability of formulation according to change in oleic acid content in polysorbate 80
  • Example 1 when the oleic acid content of the total fatty acids in polysorbate 80 was about 85 wt% or less, the formulation had excellent stability, but when the oleic acid content exceeded about 87 wt%, the stability of the formulation was rapidly reduced.
  • Formulations (b) to (e) were prepared which were 75 wt%, 80 wt%, 85 wt% and 90 wt%, respectively (see Table 4).
  • the formulation containing the taxane compound according to the present invention as an active ingredient has extremely excellent stability because generation of related substances such as decomposition products is remarkably reduced even when stored for a long period of time, for example, 8 weeks or more, and particularly at high humidity and temperature, etc. It shows very good stability even under severe conditions of
  • the formulation containing the taxane compound according to the present invention as an active ingredient does not use a toxic organic solvent such as ethanol, so side effects can be minimized.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne une nouvelle formulation pharmaceutique présentant une stabilité améliorée contenant un taxane ou un sel pharmaceutiquement acceptable de celui-ci, et son procédé de fabrication. La formulation contenant en tant que principe actif un composé à base de taxane selon la présente invention présente une réduction remarquable de la génération de substances apparentées, tels que des produits dégradés, même lorsqu'elle est stockée pendant une longue période de temps, par exemple 8 semaines ou plus, et est ainsi très stable, et présente une excellente stabilité même dans des conditions difficiles, telles qu'une humidité et des températures élevées. En outre, la formulation contenant en tant que principe actif un composé à base de taxane selon la présente invention n'utilise pas de solvant organique toxique, tel que l'éthanol, etc, ce qui conduit à des effets secondaires minimisés.
PCT/KR2021/003717 2020-03-25 2021-03-25 Nouvelle formulation pharmaceutique à stabilité améliorée contenant du taxane, un sel pharmaceutiquement acceptable de celui-ci, ou un hydrate de celui-ci WO2021194280A1 (fr)

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KR1020200035974A KR102401546B1 (ko) 2020-03-25 2020-03-25 탁산, 이의 약학적으로 허용되는 염, 또는 그의 수화물을 함유하는 안정성이 향상된 신규 약제학적 제형
KR10-2020-0035974 2020-03-25

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KR102401546B1 (ko) * 2020-03-25 2022-05-27 주식회사 보령 탁산, 이의 약학적으로 허용되는 염, 또는 그의 수화물을 함유하는 안정성이 향상된 신규 약제학적 제형

Citations (5)

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KR20080030024A (ko) * 2005-06-17 2008-04-03 호스피라 오스트레일리아 피티와이 리미티드 도세탁셀의 약제학적 액상제제
US20080306137A1 (en) * 2006-02-20 2008-12-11 Beijing Century Biocom Pharmaceutical Technology Co., Ltd. Pharmaceutical compositions comprising docetaxel and methods for preparation thereof
EP2875814A1 (fr) * 2012-07-19 2015-05-27 FUJIFILM Corporation Composition liquide contenant un principe actif à base de taxane, son procédé de fabrication et préparation médicinale liquide
KR20150066542A (ko) * 2012-10-01 2015-06-16 테이코쿠 팔마 유에스에이, 인코포레이티드 비수성 탁산 나노분산 제형 및 이의 사용 방법
KR20200038895A (ko) * 2020-03-25 2020-04-14 보령제약 주식회사 탁산, 이의 약학적으로 허용되는 염, 또는 그의 수화물을 함유하는 안정성이 향상된 신규 약제학적 제형

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KR100737742B1 (ko) * 2005-12-05 2007-07-10 대화제약 주식회사 파클리탁셀 조성물의 제조 방법
KR101053780B1 (ko) * 2008-02-29 2011-08-02 동아제약주식회사 도세탁셀을 함유하는 단일액상의 안정한 약제학적 조성물
KR101093720B1 (ko) * 2009-03-06 2011-12-19 지웅길 주사제용 항암제 조성물

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20080030024A (ko) * 2005-06-17 2008-04-03 호스피라 오스트레일리아 피티와이 리미티드 도세탁셀의 약제학적 액상제제
US20080306137A1 (en) * 2006-02-20 2008-12-11 Beijing Century Biocom Pharmaceutical Technology Co., Ltd. Pharmaceutical compositions comprising docetaxel and methods for preparation thereof
EP2875814A1 (fr) * 2012-07-19 2015-05-27 FUJIFILM Corporation Composition liquide contenant un principe actif à base de taxane, son procédé de fabrication et préparation médicinale liquide
KR20150066542A (ko) * 2012-10-01 2015-06-16 테이코쿠 팔마 유에스에이, 인코포레이티드 비수성 탁산 나노분산 제형 및 이의 사용 방법
KR20200038895A (ko) * 2020-03-25 2020-04-14 보령제약 주식회사 탁산, 이의 약학적으로 허용되는 염, 또는 그의 수화물을 함유하는 안정성이 향상된 신규 약제학적 제형

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