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WO2020180093A2 - Composition pharmaceutique contenant de l'oseltamivir - Google Patents

Composition pharmaceutique contenant de l'oseltamivir Download PDF

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Publication number
WO2020180093A2
WO2020180093A2 PCT/KR2020/003030 KR2020003030W WO2020180093A2 WO 2020180093 A2 WO2020180093 A2 WO 2020180093A2 KR 2020003030 W KR2020003030 W KR 2020003030W WO 2020180093 A2 WO2020180093 A2 WO 2020180093A2
Authority
WO
WIPO (PCT)
Prior art keywords
soluble polymer
granular formulation
formulation
granules
water
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/KR2020/003030
Other languages
English (en)
Korean (ko)
Other versions
WO2020180093A3 (fr
Inventor
김상욱
임현태
송호준
김정태
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.)
CorePharmBio Co Ltd
Original Assignee
CorePharmBio 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 CorePharmBio Co Ltd filed Critical CorePharmBio Co Ltd
Priority to MX2021010596A priority Critical patent/MX2021010596A/es
Publication of WO2020180093A2 publication Critical patent/WO2020180093A2/fr
Publication of WO2020180093A3 publication Critical patent/WO2020180093A3/fr
Priority to MX2025012658A priority patent/MX2025012658A/es
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
    • 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
    • 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
    • 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
    • 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
    • A61K9/1617—Organic compounds, e.g. phospholipids, fats
    • A61K9/1623—Sugars or sugar alcohols, e.g. lactose; Derivatives thereof; Homeopathic globules
    • 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
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • 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
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5021—Organic macromolecular compounds
    • A61K9/5026—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
    • 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
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5021—Organic macromolecular compounds
    • A61K9/5036—Polysaccharides, e.g. gums, alginate; Cyclodextrin
    • A61K9/5042—Cellulose; Cellulose derivatives, e.g. phthalate or acetate succinate esters of hydroxypropyl methylcellulose
    • A61K9/5047—Cellulose ethers containing no ester groups, e.g. hydroxypropyl methylcellulose

Definitions

  • the present invention relates to a pharmaceutical composition containing oseltamivir or a pharmaceutically acceptable salt thereof.
  • Oseltamivir (oseltamivir) is a new flu or as the therapeutic agent of Tamiflu (Tamiflu) ® active component of the influenza A (H1N1), referred to as the flu, is used as oseltamivir form builder phosphate (oseltamivir phosphate), suspensions or capsules It is formulated as zero.
  • Oseltamivir suspension is inconvenient to prepare a suspension syrup by mixing the correct amount of water when ingested.
  • patients especially in children's patients
  • severe bitterness due to insoluble foreign substances that are not homogeneously suspended when taking
  • the medication compliance is poor.
  • oseltamivir When oseltamivir is formulated as a capsule, there is a large amount of active ingredient to be contained per unit capsule, and since the active ingredient raw material used is fine powder, the flowability is poor, which may lead to defects when filling the capsule, thereby increasing productivity. Falling problems arise. In addition, capsules are not easy to take for patients with dysphagia who cannot swallow well, for example, elderly or child patients.
  • capsules can obtain the effect of masking the taste and flavor of the drug due to the effect of delaying the disintegration time (delayed drug release) of the formulation itself and the time it takes for the film on the surface to break.
  • disintegration time delayed drug release
  • Patent Document 1 Korean Registered Patent Publication No. 447096
  • the present invention is to provide a pharmaceutical composition containing oseltamivir or a pharmaceutically acceptable salt thereof with improved medication compliance.
  • the core in order to solve the problem of low medication compliance, the core; A drug layer surrounding the core and comprising oseltamivir or a pharmaceutically acceptable salt thereof (eg, oseltamivir phosphate); And a coating layer surrounding the drug layer and comprising a water-soluble polymer and a poorly water-soluble polymer.
  • oseltamivir or a pharmaceutically acceptable salt thereof eg, oseltamivir phosphate
  • a coating layer surrounding the drug layer and comprising a water-soluble polymer and a poorly water-soluble polymer.
  • the oseltamivir-containing granular formulation according to the present invention has a little bitter taste and/or masking of the bitter taste of the active ingredient, has little foreign body sensation and residual sensation, and can be taken without water.
  • 1 and 2 are graphs showing the results of evaluating bitter taste shielding, foreign body sensation, residual sensation, and dissolution time in the oral cavity for a composition prepared according to an embodiment of the present invention and a composition prepared in a comparative example.
  • the present invention core; A drug layer surrounding the core and comprising oseltamivir or a pharmaceutically acceptable salt thereof (eg, oseltamivir phosphate); And a coating layer surrounding the drug layer and comprising a water-soluble polymer and a poorly water-soluble polymer.
  • oseltamivir or a pharmaceutically acceptable salt thereof (eg, oseltamivir phosphate)
  • a coating layer surrounding the drug layer and comprising a water-soluble polymer and a poorly water-soluble polymer.
  • the present invention relates to a granule formulation containing the granules.
  • the core may contain sugar or sugar alcohol, or may be made of sugar or sugar alcohol.
  • the core is one or more selected from the group consisting of xylitol, sorbitol, sucrose, mannitol, isomalt, maltitol, lactose, inositol, erythritol, fructose, trehalose, arabitol, galactitol, lactitol, and maltotritol. Can be.
  • the average particle size (D50) of the core is preferably 150 ⁇ 250 ⁇ m (Sympatec HELOS (HI 199) particle size analyzer & RODOS, R5: 0.5/4.5... 875 ⁇ m).
  • the drug layer may further include a water-soluble polymer binder.
  • the binder may be selected from one or more of hydroxypropyl cellulose, hydroxypropylmethyl cellulose, povidone and copovidone.
  • the drug layer may further include a high sweetener.
  • High sweeteners that can be used may be selected from one or more of enzyme-treated stevia, steviosides, aspartame, saccharin salt, neotam, sucralose, acesulfame potassium, and tomatoatin.
  • the high sweetener may be contained in an amount of 0.2 to 5% by weight based on the total weight of the core and the drug layer surrounding it.
  • the poorly water-soluble polymer included in the coating layer may be selected from ethylcellulose, methylcellulose and Eudragit (eg, Eudragit L100 or Eudragit S100).
  • the water-soluble polymer included in the coating layer may be selected from one or more of hydroxypropyl cellulose, hydroxypropylmethyl cellulose, polyvinylpyrrolidone, and copovidone.
  • the total weight of the water-soluble polymer and the poorly water-soluble polymer contained in the coating layer is preferably 4 to 10% by weight based on the total weight of the granules according to the present invention.
  • the mass ratio of the water-soluble polymer and the poorly water-soluble polymer included in the coating layer is preferably 0.33:1 to 3:1, preferably 0.5:1 to 2:1.
  • the poorly water-soluble polymer included in the coating layer is preferably contained in an amount of 1.5 to 7% by weight based on the total weight of the granules. Outside the above range, when the poorly water-soluble polymer is less than 1.5% by weight, the bitter taste shielding effect is deteriorated, whereas when the poorly water-soluble polymer is more than 7% by weight, a foreign body sensation or residual sensation in the oral cavity remains when taken orally.
  • the granules may be formulated into a granule formulation by mixing with sugar or sugar alcohol or by adding a flavoring agent thereto.
  • oseltamivir or a pharmaceutically acceptable salt thereof according to the present invention comprises a core; A drug layer surrounding the core and comprising oseltamivir or a pharmaceutically acceptable salt thereof (eg, oseltamivir phosphate); And granules surrounding the drug layer and including a coating layer including a water-soluble polymer and a poorly water-soluble polymer, and sugar or sugar alcohol.
  • Sugars or sugar alcohols that can be mixed with the granules in the present invention are xylitol, sorbitol, sucrose, mannitol, isomalt, maltitol, lactose, inositol, erythritol, fructose, trehalose, arabitol, and the like that can be used as the core. At least one type may be selected from the group consisting of galactitol, lactitol, and maltotritol.
  • a flavoring agent having a scent such as cherry flavor, strawberry, banana, grape, lemon, orange, chocolate or mint may be used.
  • the granular formulation according to the present invention means a granule or a powder.
  • the granules according to the present invention contain drugs by dissolving or dispersing oseltamivir or a pharmaceutically acceptable salt thereof, a high sweetener, and a water-soluble polymer binder in a solvent (for example, water, ethanol, or a mixture of water and ethanol).
  • a solvent for example, water, ethanol, or a mixture of water and ethanol.
  • step (A) preparing a liquid;
  • step (B) coating the drug-containing liquid prepared in step (a) on the core to obtain first granules;
  • step (C) dissolving or dispersing a water-soluble polymer and a poorly water-soluble polymer in a solvent (eg, water, ethanol, or a mixture of water and ethanol) to prepare a coating solution;
  • a solvent eg, water, ethanol, or a mixture of water and ethanol
  • the granule formulation according to the present invention may be prepared through the step (e) of further mixing the second granules with sugar or sugar alcohol.
  • the first granule means a granule in which a drug layer containing a drug surrounds the core.
  • the second granule refers to a granule in which a coating layer including a water-soluble polymer and a poorly water-soluble polymer surrounds the first granule.
  • the granular formulation according to the present invention means a granule or a powder.
  • the present invention provides a method for preventing or treating an infection caused by influenza A or influenza B virus comprising administering the granular formulation to a mammal, including humans, in a therapeutically effective amount.
  • therapeutically effective amount is an amount effective for preventing or treating an infection caused by influenza A or influenza B virus, for example, as an amount of a granular formulation administered to a subject to be treated, the occurrence of infectious disease caused by influenza A or influenza B virus. Or granules that prevent recurrence, alleviate symptoms, inhibit direct or indirect pathological consequences, prevent metastasis, reduce the rate of progression, alleviate or temporarily alleviate the condition, or improve prognosis Any amount of formulation may be included. That is, the therapeutically effective amount can be interpreted as encompassing all doses in which symptoms of an infection caused by influenza A or influenza B virus are improved or cured by the granular formulation.
  • the method for preventing or treating infectious diseases caused by influenza A or influenza B virus includes not only dealing with the disease itself before the onset of symptoms, but also inhibiting or avoiding the symptoms thereof by administering a granular formulation.
  • the prophylactic or therapeutic dose of a particular active ingredient will vary depending on the nature and severity of the disease or condition and the route to which the active ingredient is administered.
  • the dose and frequency of dose will vary depending on the age, weight and response of the individual patient.
  • a suitable dosage regimen can be readily selected by one of ordinary skill in the art taking these factors of course into account.
  • the prophylaxis or treatment method of the present invention may further include administration of a therapeutically effective amount of an additional active agent useful in the prevention or treatment of an infection caused by influenza A or influenza B virus together with a granular formulation, and additional The active agent may exhibit a synergistic or additive effect together with the granular formulation.
  • the mammals including humans include mammals such as humans, monkeys, cows, horses, dogs, cats, rabbits, and rats.
  • the present invention provides the use of the granular formulation for use in the preparation of an infectious disease agent caused by influenza A or influenza B virus.
  • the present invention provides the use of the granular formulation for the treatment of infectious diseases caused by influenza A or influenza B virus.
  • the granular formulation of the present invention for the preparation of an infectious disease agent caused by influenza A or influenza B virus may contain an acceptable carrier or the like, and may further include other agents.
  • composition of Table 1 a pharmaceutical composition (granule formulation) containing oseltamivir phosphate as an active ingredient was prepared.
  • oseltamivir phosphate active ingredient
  • hydroxypropyl cellulose a water-soluble polymeric binder
  • enzyme-treated stevia high sweetener
  • talc pharmaceutically acceptable additives
  • the drug-containing liquid is coated on the xylitol (core) by flowing the prepared drug-containing liquid into a fluidized bed while flowing the xylitol of the indicated amount in the first granular part.
  • the fluid bed coater is operated with the parameters shown in Table 2 below.
  • the core coated with the drug-containing liquid is dried to obtain a first granular part.
  • hydroxypropylmethyl cellulose water-soluble polymer
  • ethyl cellulose poorly water-soluble polymer
  • pharmaceutically acceptable additives citric acid (flavoring agent), talc (lubricant)
  • citric acid flavoring agent
  • talc lubricant
  • the second granules are mixed with xylitol (sugar alcohol), sucralose (high sweetener), cherry flavored Lace (flavoring agent), and a pharmaceutically acceptable additive (talc) to prepare a granular formulation.
  • xylitol sucgar alcohol
  • sucralose high sweetener
  • cherry flavored Lace flavoring agent
  • talc pharmaceutically acceptable additive
  • compositions of Examples 6 to 9 were prepared according to the manufacturing method of Examples 1 to 5.
  • compositions of Examples 10 to 13 were prepared according to the manufacturing method of Examples 1 to 5.
  • the mass ratio of the water-soluble polymer and the poorly water-soluble polymer contained in the secondary granules has a value in the range of 0.5:1 to 2:1.
  • Comparative Examples 1 to 4 are compositions comprising a water-soluble polymer or a poorly water-soluble polymer alone in the coating layer of the secondary granules.
  • compositions of Comparative Examples 1 to 4 were prepared according to the preparation method of Examples 1 to 5:
  • Comparative Example 5 was prepared according to the preparation method of Examples 1 to 5 (however, a binder (hydroxypropyl cellulose) was not used in the drug-containing liquid when preparing the first granules.
  • Comparative Example 6 was prepared by simple mixing by weighing each component of Table 7 below.
  • Comparative Example 7 granules were prepared by a conventional wet granulation method when preparing the primary granules.
  • the prepared primary granules are mixed with xylitol, placed in a fluidized bed coater and flowed, and coated by spraying a coating solution in which ethyl cellulose, hypromellose, and talc are dissolved or dispersed in ethanol to prepare secondary granules.
  • a granule formulation was prepared by adding sucralose, xylitol, cherry flavored Lace, and talc to the second granule, followed by mixing.
  • Example 8 is a composition prepared by mixing granules composed of oseltamivir phosphate and xylitol after mixing with sugar alcohol and sweetener.
  • Table 10 below is an evaluation criterion, and Tables 11 to 13 show the result tables for each subject scoring.
  • Table 14 below is an evaluation criterion, and Tables 15 to 17 show the results scored by each subject in a table.
  • Table 18 below is an evaluation criterion
  • Tables 19 to 21 show the results scored by the subject in a table.
  • the pharmaceutical compositions prepared in Examples 1 to 13 and Comparative Examples 1 to 8 were evaluated for dissolution time in the oral cavity while dissolving in the oral cavity in 20 healthy adults.
  • the dissolution time in the oral cavity was measured using a stopwatch from the time when the oral formulation was administered to the time completely dissolved. In all trials, test subjects were kept blind.
  • Tables 22 to 24 below are tables showing the results measured by each subject (unit: seconds).
  • composition of the Example prepared according to the present invention showed satisfactory results in terms of bitter taste shielding, foreign body sensation, residual sensation, and dissolution rate when compared to the composition of Comparative Example.
  • the oseltamivir granule formulation according to the present invention minimizes the feeling of foreign body and residual feeling while shielding the bitter taste, and can be quickly dissolved in the oral cavity, greatly improving the convenience of taking medicine.

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  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (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)
  • Emergency Medicine (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne une formulation de granulé comprenant de l'oseltamivir ou ses sels pharmaceutiquement acceptables.
PCT/KR2020/003030 2019-03-05 2020-03-04 Composition pharmaceutique contenant de l'oseltamivir Ceased WO2020180093A2 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
MX2021010596A MX2021010596A (es) 2019-03-05 2020-03-04 Composicion farmaceutica que contiene oseltamivir.
MX2025012658A MX2025012658A (es) 2019-03-05 2021-09-02 Composicion farmaceutica que contiene oseltamivir

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020190025018A KR20200106607A (ko) 2019-03-05 2019-03-05 오셀타미비르 함유 의약 조성물
KR10-2019-0025018 2019-03-05

Publications (2)

Publication Number Publication Date
WO2020180093A2 true WO2020180093A2 (fr) 2020-09-10
WO2020180093A3 WO2020180093A3 (fr) 2020-12-10

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PCT/KR2020/003030 Ceased WO2020180093A2 (fr) 2019-03-05 2020-03-04 Composition pharmaceutique contenant de l'oseltamivir

Country Status (3)

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KR (2) KR20200106607A (fr)
MX (2) MX2021010596A (fr)
WO (1) WO2020180093A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113876719A (zh) * 2021-11-02 2022-01-04 哈药集团技术中心 一种奥司他韦干糖浆剂及其制备方法

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KR20230173533A (ko) * 2022-06-17 2023-12-27 주식회사 코아팜바이오 신규한 구강용해산 조성물
TW202536011A (zh) 2024-01-16 2025-09-16 日商住友化學股份有限公司 抗蝕劑組成物、抗蝕劑圖案的製造方法及鍍覆造型物的製造方法

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SI9620042A (sl) 1995-02-27 1998-12-31 Gilead Sciences, Inc. Novi selektivni inhibitorji virusnih ali bakterijskih neuraminidaz
JP2009528294A (ja) * 2006-02-23 2009-08-06 エリモス・ファーマスーティカルズ・エルエルシー インフルエンザウイルス感染症の治療方法
CN1820744B (zh) * 2006-04-04 2011-01-26 中国人民解放军军事医学科学院毒物药物研究所 磷酸奥司他韦颗粒剂及其制备方法
KR20100052262A (ko) * 2008-11-10 2010-05-19 (주)아모레퍼시픽 난용성 약물의 나노입자를 포함하는 분말의 제조방법, 그에의해 제조된 분말 및 이를 포함하는 약학적 조성물
CN105102001B (zh) * 2012-08-28 2017-12-26 原创生医股份有限公司 含金属的复合微胞药物载体的触发释放方法
CA2930105A1 (fr) * 2013-11-13 2015-05-21 Vertex Pharmaceuticals Incorporated Formulations de composes aza-indole

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113876719A (zh) * 2021-11-02 2022-01-04 哈药集团技术中心 一种奥司他韦干糖浆剂及其制备方法

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Publication number Publication date
KR20240158209A (ko) 2024-11-04
WO2020180093A3 (fr) 2020-12-10
KR20200106607A (ko) 2020-09-15
MX2025012658A (es) 2025-11-03
MX2021010596A (es) 2021-09-23

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