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WO2016159572A1 - Formulation orale solide contenant de l'oseltamivir, et son procédé de préparation - Google Patents

Formulation orale solide contenant de l'oseltamivir, et son procédé de préparation Download PDF

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Publication number
WO2016159572A1
WO2016159572A1 PCT/KR2016/003021 KR2016003021W WO2016159572A1 WO 2016159572 A1 WO2016159572 A1 WO 2016159572A1 KR 2016003021 W KR2016003021 W KR 2016003021W WO 2016159572 A1 WO2016159572 A1 WO 2016159572A1
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WO
WIPO (PCT)
Prior art keywords
oseltamivir
solid preparation
oral solid
granules
organic acid
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.)
Ceased
Application number
PCT/KR2016/003021
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English (en)
Korean (ko)
Inventor
이승준
조정현
김진철
김용일
박재현
우종수
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.)
Hanmi Pharmaceutical Co Ltd
Hanmi Pharmaceutical Industries Co Ltd
Original Assignee
Hanmi Pharmaceutical Co Ltd
Hanmi Pharmaceutical Industries Co Ltd
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 Hanmi Pharmaceutical Co Ltd, Hanmi Pharmaceutical Industries Co Ltd filed Critical Hanmi Pharmaceutical Co Ltd
Priority to CN201680011569.5A priority Critical patent/CN107567332B/zh
Publication of WO2016159572A1 publication Critical patent/WO2016159572A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • 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
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0048—Eye, e.g. artificial tears
    • A61K9/0051—Ocular inserts, ocular implants
    • 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
    • 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
    • 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
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4841—Filling excipients; Inactive ingredients
    • A61K9/4858—Organic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses

Definitions

  • the present invention relates to a solid preparation comprising oseltamivir or a pharmaceutically acceptable salt thereof, and more particularly, it has a high initial dissolution rate and a low dissolution deviation compared to conventional oseltamivir formulations to ensure the stability of the active ingredient.
  • the present invention relates to an oseltamivir-containing oral solid preparation and a method for producing the same.
  • flu or Tamiflu ® is used as a therapeutic agent for influenza A (H1N1), it referred to as swine flu and containing oseltamivir phosphate (oseltamivir phosphate) as a main component, and is formulated as a suspension agent or capsule.
  • oseltamivir phosphate has a large amount of active ingredient to be contained per unit capsule when formulated as a capsule (30mg, 45mg, 75mg).
  • oseltamivir phosphate is known to have higher storage stability than oseltamivir free base, but even if the particle size is adjusted to increase the dissolution rate, the desired initial dissolution rate is not easily obtained, and the dissolution rate is high. There is this.
  • oseltamivir free base is advantageously pharmaceutical in that the initial dissolution rate is remarkably excellent and the variation in dissolution rate is low.
  • the oseltamivir free base has a lower molecular weight than the oseltamivir phosphate, the content of the active ingredient to be filled in the capsule is relatively small, so the productivity for preparing capsules is higher than that of the oseltamivir phosphate.
  • An object of the present invention is to increase the stability of the active ingredient of a formulation containing oseltamivir free base by more than or equal to that of oseltamivir phosphate, thereby providing a higher initial dissolution rate and a lower dissolution deviation and a higher productivity than a commercial formulation. It is to provide an oral solid preparation containing oseltamivir free base that can ensure a high but stable stability of the active ingredient.
  • Another object of the present invention is to provide a method for preparing an oseltamivir free base-containing oral solid preparation.
  • An oral solid preparation containing an organic acid is provided.
  • a granulation step of preparing granules comprising oseltamivir or a pharmaceutically acceptable salt thereof, a diluent, a disintegrant, and a binder;
  • the solid preparation containing the oseltamivir free base according to the present invention has an equivalent or more stability compared to the oseltamivir phosphate-containing preparation by including an organic acid as a stabilizer. Therefore, according to the present invention has an advantage in the initial dissolution rate is superior to the conventional Tamiflu capsules, and the dissolution deviation is small and effective while producing a capsule, while having the advantages of high productivity, the stability of the active ingredient also contains the oseltamivir-containing solid preparation Can be provided.
  • An oral solid preparation containing an organic acid is provided.
  • organic acid is a generic term for organic compounds that exhibit acidity. Specifically, carboxylic acid, sulfonic acid, sulfinic acid, sulfenic acid, phenol, enol, thiol, phosphonic acid, phosphoric acid, boronic acid, imide acid, It is a compound which has an acidic functional group (this is abbreviated as "acidic functional group” suitably hereafter), such as a hydrazone acid, a hydroxic acid, and a hydroxamic acid.
  • acidic functional group an acidic functional group
  • the organic acid may serve as a stabilizer to increase the stability of the active ingredient oseltamivir.
  • One type may be used for the said organic acid, and may be used for it combining several types of organic acid.
  • the organic acid is an organic acid having 1 to 5 carbon atoms, and includes an organic acid having a carboxylic acid.
  • the organic acid having the carboxylic acid may be an organic acid having 1 to 5 carbon atoms and having two carboxylic acid functional groups, for example malonic acid, succinic acid, tartaric acid, fumaric acid, glutaric acid, any combination thereof, and the like. There is, but is not limited to this.
  • the organic acid is tartaric acid, fumaric acid, or a combination thereof.
  • the amount suitable for stabilization may be determined according to specific components of the organic acid, for example, present in an amount of about 0.3 to 6% by weight based on the total content of the solid preparation, and more specifically, based on the total content of the solid preparation. It may be present in an amount of about 0.5 to 5% by weight.
  • the oseltamivir or a pharmaceutically acceptable salt thereof includes oseltamivir free base or oseltamivir phosphate, and may also include any other pharmaceutically acceptable salt.
  • the active ingredient of the solid preparation is oseltamivir free base
  • oseltamivir free base is the average particle size (d (0.9) ) of the lower 90% of the particles of less than 200 ⁇ m Particle size, more specifically may have a particle size of 10 ⁇ m to 200 ⁇ m.
  • the "average particle size size (d (0.9) ) of particles of the lower 90%” is the average of the particles corresponding to 90% of the total number of particles from the smallest particles when the particle size is measured using a particle size measuring device. It means particle size.
  • oseltamivir free base is known to be less stable than oseltamivir phosphate, oseltamivir free base has a higher initial dissolution rate than the oseltamivir phosphate by controlling the particle size, and the dissolution rate is small. There is this (PCT / KR2015 / 006128).
  • oseltamivir free base has a lower molecular weight than oseltamivir phosphate has a pharmaceutical advantage that can be produced with higher productivity because the amount of the active ingredient-containing mixture to be filled into the capsule when the capsule is prepared.
  • Oral solid preparations according to the present invention can sufficiently stabilize the oseltamivir free base due to the use of the organic acid (see Test Example 3). Therefore, the oral solid preparation may have the stability of the active ingredient similar to the case of containing oseltamivir phosphate while containing oseltamivir free base as the active ingredient, the solid preparation is the initial compared to the oseltamivir phosphate Oseltamivir free base, which has pharmaceutical superiority in dissolution rate and capsule productivity, has the advantage that it can be used as an active ingredient.
  • the oral solid preparation may be any solid preparation known in the art.
  • the oral solid preparation is an oral solid preparation containing granules comprising oseltamivir or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable additive.
  • the organic acid may be contained during the preparation of the granules. Being contained during the preparation of the granules means that it can be added and prepared at any stage of the granules manufacturing process, and in particular, a binder containing a binder in a mixture comprising the active ingredient, diluent and disintegrant It may be added to or contained in the post-mixing with the disintegrating and glidants after granulation, or a combination thereof.
  • the person skilled in the art may appropriately select the addition step of the organic acid according to the specific manufacturing method of the granules.
  • the organic acid may be determined in an amount suitable for stabilization according to the specific components of the organic acid, for example, may be present in an amount of about 0.3 to 6% by weight in the oral solid preparation containing the granules, and more specifically, the solid It may be present in the formulation in an amount of about 0.5-5% by weight.
  • the organic acid is tartaric acid, the content of tartaric acid in the solid preparation is about 0.3 to 6% by weight.
  • the organic acid is fumaric acid, the content of fumaric acid in the solid preparation is about 0.3 to 6% by weight (Test Example 4).
  • the granules have a water content of about 3.5% by weight or less. If the water content is high, the stability of the active ingredient may be reduced (see Test Example 5).
  • the pharmaceutically acceptable additive may be selected from the group consisting of diluents, disintegrants, binders, glidants, and any combination thereof, in one embodiment including all of the diluents, disintegrants, binders, and glidants. .
  • the diluent may be used in the preparation of granules, and any diluent which does not affect the action of the active ingredient may be used, for example, pregelatinized starch, mannitol, lactose, microcrystalline cellulose, and any combination thereof. Diluents selected from the group consisting of may be used, but are not limited thereto.
  • the disintegrant may be used in the preparation of granules, and any disintegrant which does not affect the action of the active ingredient may be used, for example, croscarmellose sodium, crospovidone, sodium glycolate starch and low-substituted hydroxy.
  • Disintegrants selected from the group consisting of propylcellulose, and any combination thereof may be used, but are not limited thereto.
  • the binder may be used in the manufacture of granules, and any binder may be used that does not affect the action of the active ingredient.
  • the binder may be a hydrophilic binder.
  • the hydrophilic binder may for example be selected from the group consisting of povidone, hydroxypropyl cellulose, hydroxypropyl methyl cellulose, hard anhydrous silicic acid, aluminum silicate, calcium silicate, calcium hydrogen phosphate, calcium carbonate, and any combination thereof.
  • the hydrophilic binder is povidone, hydroxypropyl cellulose, or a combination thereof.
  • Oral solid preparations containing the granules may be granules, tablets, capsules, or dry syrups.
  • the oral solid preparation is a capsule, and includes oseltamivir free base as an active ingredient. Since the solid preparation contains oseltamivir free base, the molecular weight is lower than that of oseltamivir phosphate, so that the amount of the mixture to be filled in the empty capsule is relatively small. Therefore, the solid preparation is preferred because it can be manufactured with high productivity while securing the stability of the active ingredient as conventional commercial preparations, and can have a high initial dissolution rate and a low dissolution deviation.
  • the oral solid preparation is a capsule, and includes an oseltamivir free base as an active ingredient, and the oseltamivir free base has an average particle size (d (0.9) of the lower 90% of the particles. ) ) May have a particle size of about 200 ⁇ m or less, more specifically about 10 ⁇ m to 200 ⁇ m.
  • the capsule of the capsule may be any capsule widely used in the art, for example, gelatin capsules, gelatin-PEG capsules, or HPMC (hydroxypropylmethylcellulose) capsules.
  • the capsule is a capsule having a moisture content of about 3 to 7% by weight, and the capsule is specifically, but is not limited to HPMC capsules.
  • a granulation step of preparing granules comprising oseltamivir or a pharmaceutically acceptable salt thereof, a diluent, a disintegrant, and a binder;
  • the granule manufacturing step may be prepared according to any granule manufacturing method known in the art, and may be prepared by wet granulation method or dry granulation method.
  • the wet granulation method may perform a process of granulating and drying a mixture containing oseltamivir or a pharmaceutically acceptable salt, diluent and disintegrant thereof in association with a binding solution.
  • the organic acid may be mixed in addition to the mixture, the binder liquid, or both the mixture and the binder liquid.
  • the solvent for preparing the binder solution may be water, ethanol, isopropanol, acetone, or a combination thereof.
  • the binder solution can be prepared by adding to the solvent, in addition to the binder, additional additives commonly used in the pharmaceutical art, such as surfactants, buffers, or combinations thereof.
  • the binder solution is prepared by dissolving a hydrophilic binder in ethanol.
  • the drying process takes into account the stability of the active ingredient, a temperature not exceeding about 60 ° C., preferably a temperature not exceeding about 50 ° C., more preferably a temperature not exceeding about 40 ° C., most preferably about It may be carried out through air drying, fluid bed drying, oven drying or microwave drying at a temperature of 20 °C to 40 °C.
  • the dry granulation method may use roller compacting or slugging a mixture comprising oseltamivir or a pharmaceutically acceptable salt and diluent, disintegrant, and binder thereof.
  • roller compaction method refers to a method of producing granules by compacting at a constant pressure while passing powder between two rollers.
  • the roller pressing method may be performed using a roller compactor.
  • the roller-compressed mixture may then be further subjected to grinding and sizing as necessary using a fitz-mill, oscillator or the like to obtain granules of suitable size.
  • the organic acid may be contained in addition to a mixture containing oseltamivir or a pharmaceutically acceptable salt and diluent, disintegrant, and binder thereof.
  • the disintegrant may be any disintegrant used in the manufacture of capsules containing granules, for example croscarmellose sodium, crospovidone, glycolic acid Minute sodium, low substituted hydroxypropyl cellulose, and any combination thereof may be selected.
  • the disintegrant is croscarmellose sodium.
  • the lubricant may be selected from the group consisting of magnesium stearate, talc, sodium stearyl fumarate, and any combination thereof, in one embodiment the lubricant is a combination of talc and sodium stearyl fumarate.
  • the organic acid may be added and mixed.
  • the formulating step can be carried out according to any method known in the art of formulating into a solid formulation using granules, and for example, to any known method of formulating into tablets, capsules, or dry syrups. Can be performed accordingly.
  • oseltamivir (Inistestee, Korea) into a 100 mL volumetric flask and add 10 mL of distilled water to dissolve it. Subsequently, oseltamivir was forcedly decomposed according to the forced decomposition experiment method described by the strong acid, the weak acid, the strong base, and the weak base described below.
  • each sample obtained in the decomposition experiment was added with an extract (a mixture of 245 mL of methanol, 135 mL of acetonitrile, and 620 mL of 0.01 N phosphoric acid) to prepare a drug which was exactly 100 mL as a sample solution.
  • the obtained sample solution was measured according to the analogous material analysis method described in the USP pharmaceutical group 'Oseltamivir phosphate Capsule' to calculate the total analogous content. The results are shown in Table 1 below.
  • oseltamivir (Inestest ST) in an HDPE bottle and a Petri dish, expose it for 1 day and 3 days at 25 ° C and 90% relative humidity, and take out 100 mg of each accurately weighed into a 100 mL volumetric flask.
  • An extract (a mixture of 245 mL of methanol, 135 mL of acetonitrile and 620 mL of 0.01 N phosphoric acid) was added thereto to prepare an exactly 100 mL solution.
  • the obtained sample solution was measured according to the analogous material analysis method described in the USP pharmaceutical group 'Oseltamivir phosphate Capsule' to calculate the total analogous content. The results are shown in Table 2 below.
  • Sodium croscarmellose, talc and sodium stearyl fumarate were added to the prepared granules, followed by post-mixing to prepare granules.
  • Granules were prepared in the same composition and method as in Example 1, except that fumaric acid was used instead of tartaric acid as a stabilizer.
  • sodium croscarmellose, talc, and sodium stearyl fumarate were added and mixed to prepare oseltamivir granules.
  • Granules were prepared in the same composition and method as in Example 3, except that fumaric acid was used instead of tartaric acid as a stabilizer.
  • Tartaric acid, sodium croscarmellose, talc, and sodium stearyl fumarate were added to the granules, and mixed to prepare oseltamivir granules.
  • Granules were prepared in the same composition and method as in Example 5, except that fumaric acid was used instead of tartaric acid as a stabilizer.
  • the filling was separated from 75 mg of commercial Tamiflu ® capsules to obtain oseltamivir granules.
  • sodium croscarmellose, talc, and sodium stearyl fumarate were added and mixed to prepare oseltamivir granules.
  • Tables 3 to 4 show the components, contents, and processes of Examples and Comparative Examples.
  • Example 1 Example 2
  • Example 3 Example 4
  • Example 5 Example 6 1st blend Oseltami Beer 75.0 75.0 75.0 75.0 75.0 75.0
  • Pregelatinized starch 45.2 45.2 45.2 45.2 45.2
  • Test Example 3 Evaluation of stability of granules by organic acid type
  • the stability of the organic acid as a stabilizer is significantly increased compared with the case of not using, and showed similar stability to the commercial formulation Tamiflu (Comparative Example 1).
  • the stability difference according to the difference in the step of introducing the organic acid in the wet granulation process is significantly increased compared with the case of not using, and showed similar stability to the commercial formulation Tamiflu (Comparative Example 1).
  • Example 7 Example 8
  • Example 9 Example 10
  • Example 11 Example 12 1st blend Oseltami Beer 75.0 75.0 75.0 75.0 75.0 75.0 Pregelatinized starch 47.3 46.6 44.5 41.0 47.65 37.5 Croscarmellose Sodium 4.5 4.5 4.5 4.5 4.5 4.5 4.5 Binder Povidone 2.5 2.5 2.5 2.5 2.5 2.5 2.5 70% ethanol (7.0) (7.0) (7.0) (7.0) (7.0) (7.0) (7.0) (7.0)
  • Lead C (% by weight) Total Lead (wt%)
  • Example 7 0.20 0.40
  • Example 8 0.16 0.33
  • Example 9 0.15 0.33
  • Example 10 0.21 0.39
  • Example 11 0.26 0.53
  • Example 12 0.32 0.59
  • Test Example 5 Evaluation of stability by granule moisture (dry weight loss)
  • Example 13 Example 14
  • Example 15 Example 16 1st blend Oseltami Beer 75.0 75.0 75.0 75.0 Pregelatinized starch 45.2 45.2 45.2 45.2 Croscarmellose Sodium 4.5 4.5 4.5 4.5
  • Binder Povidone 2.5 2.5 2.5 2.5 70% ethanol (7.0) (7.0) (7.0) (7.0)
  • Moisture% (loss on drying) 1.5 2.5 3.5
  • Example 16 when the granular moisture is about 4.5% or more, a flexible substance is generated and unstable, and when the granular moisture is about 3.5% or less, as in Examples 13 to 15, it is relatively stable.
  • oseltamivir About 75 mg was taken as an oseltamivir from the granules of Example 13, and the capsule was prepared by filling into gelatin capsule No. 2 (seoheung capsule). Separately, about 75 mg of the oseltamivir was taken as an oseltamivir from the granules of Example 13, and the tablets were prepared by tableting at a hardness of about 10 in a rotary tablet press (Sejong, MRC-18).
  • Dissolution Test Method Dissolution Method 2 of the Korean Pharmacopoeia (Paddle Method)

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Abstract

La présente invention concerne : une formulation orale solide contenant de l'oseltamivir ou un de ses sels pharmaceutiquement acceptables, et un acide organique ; et un procédé de préparation associé.
PCT/KR2016/003021 2015-03-31 2016-03-25 Formulation orale solide contenant de l'oseltamivir, et son procédé de préparation Ceased WO2016159572A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201680011569.5A CN107567332B (zh) 2015-03-31 2016-03-25 含有奥司他韦的口服固体制剂及其制备方法

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KR1020150045687A KR20160117070A (ko) 2015-03-31 2015-03-31 오셀타미비어 함유 경구용 고형제제 및 그 제조방법
KR10-2015-0045687 2015-03-31

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WO2018004261A1 (fr) * 2016-06-30 2018-01-04 한미약품 주식회사 Préparation solide contenant de l'oseltamivir pour administration orale et procédé d'élaboration de préparation solide
US20220354816A1 (en) * 2019-09-27 2022-11-10 Sunshine Lake Pharma Co., Ltd. Oseltamivir formulation
CN111297823B (zh) * 2020-03-04 2021-06-18 石药集团中奇制药技术（石家庄）有限公司 一种磷酸奥司他韦胶囊的制备方法

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