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WO2019078512A1 - Nouvelle préparation semi-solide de l'udénafil - Google Patents

Nouvelle préparation semi-solide de l'udénafil Download PDF

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Publication number
WO2019078512A1
WO2019078512A1 PCT/KR2018/011677 KR2018011677W WO2019078512A1 WO 2019078512 A1 WO2019078512 A1 WO 2019078512A1 KR 2018011677 W KR2018011677 W KR 2018011677W WO 2019078512 A1 WO2019078512 A1 WO 2019078512A1
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WO
WIPO (PCT)
Prior art keywords
hydroxypropylmethylcellulose
povidone
gum
sodium
wettability
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/KR2018/011677
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English (en)
Korean (ko)
Inventor
김상욱
김영래
전은경
카드카프라카시
이홍기
김정태
김도현
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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
Publication of WO2019078512A1 publication Critical patent/WO2019078512A1/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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • 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
    • A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic 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
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
    • 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
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • 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

Definitions

  • the present invention relates to an oral anti-wrinkle agent comprising, as an active ingredient, udenapil or a pharmaceutically acceptable salt thereof.
  • the present invention relates to a medicament containing a udenapil or a pharmaceutically acceptable salt thereof, which is excellent in the bitter taste of the drug, has excellent necking, is easy to discharge from the wrapping paper, ≪ / RTI >
  • Udenapil is a drug with a bitter taste, such as bitter taste, and it is necessary to shield it for smooth taking.
  • the same PDE-5 family of drugs have also adopted free base drugs to improve their bitter taste.
  • Udenafil is a drug having a severe taste such as a bitter taste and paralysis. Therefore, in order to take a medicine smoothly, an additional gummy screening technique other than a simple drug as a free base is required.
  • the present inventor has tried to improve the compliance by taking advantage of the anti-bulb agent technique which is effective in taking the gum rounding smoothly, unlike the solid preparation such as tablets or capsules, and capable of effectively shielding the gum, unlike the liquid formulation.
  • the present invention provides a medicinal herb that is easy to take and can be gently shielded by allowing it to be taken without water in the presence of water or a pharmaceutically acceptable salt thereof.
  • the present invention provides an anti-hypertensive agent for idenafil or a pharmaceutically acceptable salt thereof which is stable during use by suppressing the characteristic Lee Sun-hyun phase of the anti-hypertensive agent.
  • the present invention overcomes the above-described problems by the following means.
  • a semi-solid preparation for oral administration comprising a udenafil or a pharmaceutically acceptable salt thereof, wherein the PAR value of the formula (1) is 50 or more and 70 or less.
  • V Volume of virtual cone (1 cm 3 )
  • the above PAR value is a value particularly suitable for the antiseptic shielding of udenafil or its pharmaceutically acceptable salts.
  • a semi-solid preparation for oral administration comprising a yildenafil or a pharmaceutically acceptable salt thereof and a wettability increasing agent, wherein the wettability increasing agent is selected from the group consisting of ammonium glycyrrhizinate, benzalkonium chloride, It is preferable to use a surfactant such as Docusate sodium, decaglycerol decaoleate, diethylene glycol monoethyl ether, dioctyl sodium sulfosuccinate, glyceryl distearate, distearate, distearate, distillate, distearate, glyceryl stearate, glyceryl ricinoeate, glycine, hexaglycerol octastearate, hydrogenated castor oil, oleic acid Oleic acid, Ploxamer, poly ethylene glycol, polyoxyethylene stearate (Polyoxy) ethylene stearates, Polyoxyl
  • wettability enhancer according to item 2, wherein Docusate sodium and Povidone are contained in an amount ranging from 0.01% to 1% by weight of docosaetate sodium, povidone, Is 0.5% to 5%, preferably 0.05% to 0.2% for docosahexa sodium, and 1% to 3% for povidone.
  • composition according to any one of 1 to 5 above, wherein the pharmaceutical composition comprises at least one enhancer, wherein the increasing agent is xanthan gum, locust bean gum, guar gum, tragacanth, gum arabic, gellan gum, Hydroxypropylcellulose, methylcellulose, hydroxyethylcellulose, hydroxypropylmethylcellulose, hydroxypropylmethylcellulose, hydroxypropylmethylcellulose, hydroxypropylmethylcellulose, hydroxypropylmethylcellulose, hydroxypropylmethylcellulose, hydroxypropylmethylcellulose, hydroxypropylmethylcellulose, hydroxypropylmethylcellulose, hydroxypropylmethylcellulose, hydroxypropylmethylcellulose, hydroxypropylmethylcellulose, hydroxypropylmethylcellulose, hydroxypropylmethylcellulose, hydroxypropylmethylcellulose, hydroxypropylmethylcellulose, hydroxypropylmethylcellulose, hydroxypropylmethylcellulose, hydroxypropylmethylcellulose, hydroxypropylmethylcellulose, hydroxypropylmethylcellulose, hydroxypropylmethylcellulose
  • the present invention seeks to minimize the bitter taste of udenapil or its pharmaceutically acceptable salts.
  • the present invention relates to a semi-thickener, which has excellent necking and is easy to discharge from a wrapping paper, thereby enhancing the convenience of taking a patient having difficulty in swallowing.
  • the present invention can improve the adherence to taking, without water, while blocking the taste of the strong-tasting drug yudenapil or its pharmaceutically acceptable salt.
  • Fig. 1 is a schematic view of the preparation, in which A1 represents the area of the bottom of the formulation and V1 represents the volume of the formulation.
  • FIG. 2 is a schematic diagram of a virtual cone, in which A2 represents the area of the bottom of a virtual cone, V2 represents the volume of the virtual cone, r represents the radius of the virtual cone bottom circle, h represents the height of the virtual cone, Represents the PAR of Equation (1).
  • FIG. 2 is a hypothetical conical model diagram having the same volume as the bottom surface of the same area as the present formulation.
  • the present inventors have unexpectedly completed the present invention by uncovering that a semi-solid preparation which, incidentally, satisfies a specific parameter condition can shield the undesirable properties of the undenafil or a pharmaceutically acceptable salt thereof as a physical form. That is, the present invention can be specified by a parameter called PAR.
  • the PAR value is a value determined by Equation 1 below.
  • V Volume of virtual cone (1 cm 3 )
  • PAR Pulseudo Angle of Repose
  • the volume of this formulation with a certain volume is placed on a flat surface and the area (A1) of the contact surface between the preparation and the floor is measured. And a virtual value representing the angle formed by the bottom surface and the oblique surface of the cone by drawing a hypothetical cone through the area A2 of the circle and the volume V1 of the present formulation 1 and 2).
  • A1 area of the bottom surface of the present product
  • A2 area of the virtual cone bottom surface circle
  • V1 (volume of the formulation) V2 (volume of the virtual cone)
  • the present invention is a new formulation of a semi-solid formulation comprising one or more thickening agents.
  • the thickener is an additive to be incorporated into the gel.
  • organic polymers are usually dispersed homogeneously in a dispersion medium so that the boundaries between the dispersion medium and the dispersion medium are not clear, and the organic polymer is an increasing agent.
  • the natural polymer include natural polysaccharides such as red alga polysaccharide, glucomannan, galactomannan, fermented polysaccharide, brown alga polysaccharide, marine invertebrate extract, starch, natural fruit extract, plant fiber derivative , Kelp, natural plant exudates or resin gums.
  • a polyethylene resin is dispersed in a dispersion medium such as water, alcohol, or oil to be used as an ointment agent.
  • the thickener may be any component capable of maintaining a semi-solid shape, but the component and content thereof should be determined so that the PAR value of Formula 1 is 50 or more and 70 or less.
  • the components and contents for realizing the PAR value of 50 or more and 70 or less can be selected by the enemy repeatedly.
  • Non-limiting examples of the thickening agent include xanthan gum, locust bean gum, guar gum, tragacanth gum, arabic gum, gellan gum, karaya gum, ghatti gum, tamarind gum, tara gum, acacia gum, agar, chitosan, Gelatin, pectin, alginic acid, sodium alginate, propylene glycol alginate, hypromellose, hydroxyethylcellulose, hydroxypropylcellulose, methylcellulose, hydroxyethylmethylcellulose, carboxymethylcellulose sodium, carboxymethylcellulose calcium, ethylcellulose , Polyethylene glycol, polyvinyl alcohol, povidone, polyethylene oxide and carbopole.
  • One embodiment of the present invention may further comprise carrageenan.
  • the present inventors surprisingly found that when the PAR value is in the range of 50 or more and 70 or less, the exact mechanism is not known, but it is found that the odenaceaf or its pharmaceutically acceptable salts are significantly reduced and the neck turnover is excellent when taken.
  • the present invention is a novel formulation which eliminates the disadvantages of liquid preparations and solid preparations and only takes advantage of them.
  • the advantages of the liquid preparation that the patient who feels dysphagia can swallow easily and the advantages of the solid preparation which is small in the size of the unit dosage form and excellent in storage and distribution.
  • the preparation is made into a formulation having a viscosity using a known polymer alone, the above advantages may not be achieved.
  • the present invention satisfies certain PAR values and is capable of realizing the advantages of both formulations.
  • additives such as a dispersion medium, a preservative, and the like can be added in addition to the thickener.
  • the dispersion medium can be selected depending on the physicochemical properties of the starting material and the thickener, and can be selected from known dispersion media such as water, alcohol or oil.
  • dispersion media such as water, alcohol or oil.
  • purified water may be adopted as a dispersion medium.
  • One or more known preservatives may be mixed, and examples thereof include methyl paraoxybenzoate and propylparaxybenzoate.
  • the content of the additive to be compounded can be adjusted by ordinary researchers. That is, it is possible to carry out a specific composition satisfying the PAR value defined in the present invention by referring to the following examples and test examples, and thus the present invention should not be construed as being limited only to the composition of a specific component.
  • a semi-solid preparation with a PAR 50-70 value of at least one incremental agent and most of the water has a problem of quality problems because the water is separated and discharged during long-term storage to reduce the volume of the bulking agent. On the contrary, if the Lee Soo Hyun phase is low, it is not easy to discharge the preparation from the packaging container.
  • Ammonium glycyrrhizinate, Benzalkonium Chloride, Docusate sodium, Decaglycerol Decaoleate, Diethylene glycol monoethyl ether (DMSO), and the like can be used as the wettability increasing agent.
  • the wettability enhancer When the wettability enhancer is used, it is possible to cause the superabsorbent phase to become worsened in the hemoglobin formulations, and the proper content of the wettability enhancer is important in order to prevent this.
  • the wettability enhancer may contain 0.01 to 5% by weight based on the total weight of each component.
  • Docusate sodium when included as the wettability increasing agent, its content is 0.01% to 1%, preferably 0.05% to 0.2%, based on the total weight.
  • the content thereof when containing povidone as an agent for increasing wettability, the content thereof is 0.5% to 5%, preferably 1% to 3%, based on the total weight.
  • the wettability enhancer includes Docusate sodium and Povidone, the contents of Docusate sodium and Povidone are 0.01% to 1% and 0.5% to 5%, respectively, %, Preferably 0.05% to 0.2%, and 1% to 3% of povidone, respectively.
  • Comparative Example 1 in which the udenafil was dispersed only in purified water was prepared.
  • EXAMPLES 1 TO 8 Preparation method: Carrageenan, Locustbean gum, Xanthan gum, Xylitol, Stevioside, Methyl paraben, Propyl paraben ), And the mixed raw materials are added to 1200 mg of purified water in the composition of Table 2, and the mixture is heated at 40 to 70 ⁇ and stirred for 1 hour or more. The remaining ingredients, including the active ingredient, are dispersed in the remaining purified water except for the 1200 mg used previously. After mixing the two prepared solutions, add the flavoring agent and disperse evenly for 20 minutes or more. Lastly, to remove bubbles and sterilize, warm to 90 °C and leave for more than 30 minutes and then cool to 25 °C ⁇ 30 °C.
  • Example 1 In all the examples except Example 1 in which the wettability enhancer was not added, the udenafil was uniformly dispersed in the semi-solidifying agent.
  • Sodium lauryl sulfate and Polysorbate 80 of Examples 4 and 5 were produced in a large amount in the production process and thus had difficulty in processing compared with other types of wettability increasing agents at the time of production.
  • the measured weight is calculated using the following formula.
  • Wt Total weight of the formulated pills, including packaging
  • each wettability enhancer should be selected so that the udenafil can be dispersed suitably in the purified water.
  • the content of the wettability enhancer varies depending on the kind of the wetting agent.
  • Test Example 2 Evaluation of Phase Behavior in Examples 9 to 13 The test was carried out in the same manner as in Test Example 1.
  • Examples 1 to 3 of this preparation are warmed to 40 to 70 ⁇ using a constant temperature water heater.
  • the PAR value is obtained by substituting into the following formula 1.
  • the measured area values are shown in Table 4 below.
  • Test Example 5 Dissolution Test In order to examine the dissolution rate of this preparation, it was added to the test solution and the dissolution test was carried out as follows.
  • This preparation was subjected to a dissolution test under the following conditions.
  • Test apparatus paddle (Korea Pharmacopoeia dissolution test method 2)
  • Test Solution pH 1.2 Test Solution (First Solution of Korean Pharmacopoeia Dissolution Test Method)
  • Example 9 was easy to chew, but felt a bitter taste.
  • Example 13 there was no bitter taste, but the bamboo hull was hard and chewed and swallowed.
  • the results of Examples 10 to 12 were confirmed to be suitable for the conditions of a semi-solid preparation for oral administration characterized by good bitter and thickening and a PAR of 50 or more and 70 or less.
  • Example 9 in which the PAR was 50 or less, it was confirmed that the physical strength of the preparation was too weak in the case of the semi-solid preparation, and the shape was easily collapsed in the oral cavity.
  • Example 13 in which the PAR exceeded 70 the physical strength of the preparation was too strong, and it was not easy to chew up the chewing gum, and it was not possible to take it without chewing, and the dissolution test also failed to exceed the standard.
  • the formulation with a PAR value of 50 ⁇ 70 was suitable for the physical strength of the preparation because it was soft at the time of taking the product, and maintained a level of effective strength for gummy shielding.
  • the dissolution test also met the dissolution rate criteria.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Nutrition Science (AREA)
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Abstract

La présente invention concerne une nouvelle formulation comprenant, en tant que matière première pharmaceutique, de l'udénafil ou un sel pharmaceutiquement acceptable de celui-ci. La présente invention peut masquer l'amertume lorsqu'un udénafil très amer ou un sel pharmaceutiquement acceptable de celui-ci est administré par voie orale, et permet une administration pratique sans eau.
PCT/KR2018/011677 2017-10-18 2018-10-02 Nouvelle préparation semi-solide de l'udénafil Ceased WO2019078512A1 (fr)

Applications Claiming Priority (2)

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KR10-2017-0135353 2017-10-18
KR1020170135353A KR20190043369A (ko) 2017-10-18 2017-10-18 유데나필의 신규한 반고형 제제

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WO2019078512A1 true WO2019078512A1 (fr) 2019-04-25

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20220096718A (ko) 2020-12-31 2022-07-07 주식회사 제뉴원사이언스 도네페질 또는 이의 약학적으로 허용되는 염을 포함하는 도네페질 젤리 제제

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20060011989A (ko) * 1996-01-12 2006-02-06 오타 세야쿠 가부시키가이샤 젤리상 경구 의약 조성물
WO2011006596A2 (fr) * 2009-07-16 2011-01-20 Ratiopharm Gmbh Solution aqueuse et composition gélatineuse contenant un inhibiteur de la phosphodiestérase-5, et procédés et utilisations correspondants
US20150216798A1 (en) * 2012-08-17 2015-08-06 Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi Novel orally administered pharmaceutical formulations
KR20160088249A (ko) * 2015-01-14 2016-07-25 애니젠 주식회사 Ｌｄｄ１７５를 유효성분으로 포함하는 발기부전 치료 또는 예방용 조성물
JP2016166178A (ja) * 2009-12-18 2016-09-15 エクソドス ライフ サイエンシーズ リミテッド パートナーシップ 末梢血管疾患を治療するための方法および組成物

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100344198B1 (ko) 1999-10-08 2002-07-19 일양약품주식회사 실데나필 시트레이트의 속효제형
KR101304343B1 (ko) 2006-04-06 2013-09-11 한미사이언스 주식회사 Ｐｄｅ-5 억제제의 경구용 속용제형

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20060011989A (ko) * 1996-01-12 2006-02-06 오타 세야쿠 가부시키가이샤 젤리상 경구 의약 조성물
WO2011006596A2 (fr) * 2009-07-16 2011-01-20 Ratiopharm Gmbh Solution aqueuse et composition gélatineuse contenant un inhibiteur de la phosphodiestérase-5, et procédés et utilisations correspondants
JP2016166178A (ja) * 2009-12-18 2016-09-15 エクソドス ライフ サイエンシーズ リミテッド パートナーシップ 末梢血管疾患を治療するための方法および組成物
US20150216798A1 (en) * 2012-08-17 2015-08-06 Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi Novel orally administered pharmaceutical formulations
KR20160088249A (ko) * 2015-01-14 2016-07-25 애니젠 주식회사 Ｌｄｄ１７５를 유효성분으로 포함하는 발기부전 치료 또는 예방용 조성물

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20220096718A (ko) 2020-12-31 2022-07-07 주식회사 제뉴원사이언스 도네페질 또는 이의 약학적으로 허용되는 염을 포함하는 도네페질 젤리 제제

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