WO2017082577A1 - Préparation solide contenant de la solifénacine amorphe à usage oral et son procédé de préparation - Google Patents

Préparation solide contenant de la solifénacine amorphe à usage oral et son procédé de préparation Download PDF

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Publication number
WO2017082577A1
WO2017082577A1 PCT/KR2016/012490 KR2016012490W WO2017082577A1 WO 2017082577 A1 WO2017082577 A1 WO 2017082577A1 KR 2016012490 W KR2016012490 W KR 2016012490W WO 2017082577 A1 WO2017082577 A1 WO 2017082577A1
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Prior art keywords
solifenacin
solid preparation
pharmaceutically acceptable
amorphous
acceptable salt
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PCT/KR2016/012490
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English (en)
Korean (ko)
Inventor
임호택
권택관
윤승빈
김용일
박재현
우종수
Original Assignee
한미약품 주식회사
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.)
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Publication date
Application filed by 한미약품 주식회사 filed Critical 한미약품 주식회사
Priority to MX2018005848A priority Critical patent/MX2018005848A/es
Priority to BR112018009413A priority patent/BR112018009413A2/pt
Priority to EA201890896A priority patent/EA201890896A1/ru
Priority to CN201680065960.3A priority patent/CN108348617A/zh
Publication of WO2017082577A1 publication Critical patent/WO2017082577A1/fr
Priority to PH12018500980A priority patent/PH12018500980A1/en

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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
    • A61K9/20—Pills, tablets, discs, rods
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/439—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom the ring forming part of a bridged ring system, e.g. quinuclidine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • 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
    • 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
    • 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
    • A61K47/38—Cellulose; Derivatives thereof

Definitions

  • the present invention relates to an oral solid preparation containing amorphous solifenacin and a method for preparing the same. More specifically, an amorphous solipenacin-containing oral solid preparation having a significantly reduced tendency to form amorphous materials and the formation of a flexible substance and its preparation It is about a method.
  • Solifenacin is a quinoline derivative having the structure of Formula 1 below, and its chemical name is (1R, 3'R) -3'-quinuclidinyl-1-phenyl-1,2,3,4-tetrahydro-2-iso Quinolinecarboxylate is:
  • the solifenacin or a pharmaceutically acceptable salt thereof has excellent selective antagonistic action on muscarinic M 3 receptors, such as neuropathy, neurogenic bladder, nocturia, unstable bladder, bladder spasms or chronic cystitis, etc. It has been reported to be useful as a prophylactic agent for respiratory diseases such as urinary diseases, chronic obstructive pulmonary diseases, chronic bronchitis, asthma and rhinitis (EP 0 801 067 A).
  • Crystalline solvenacin succinate has a problem in that the crystal form is changed to amorphous during the wet granulation process, and the softening material increases over time to reduce the stability of the tablet.
  • amorphous solifenacin has a pharmacokinetic advantage which is high in solubility compared to crystalline solifenacin.
  • the amorphous solifenacin also has a problem in that the crystal form of the main component changes according to storage conditions because it changes to a crystalline solifenacin over time.
  • the method for stabilizing the crystalline solifenacin is not effective in improving the stability of amorphous solifenacin. Therefore, there is a need for the development of oral preparations of amorphous solifenacin that can maintain the stability of the active ingredient over time.
  • Another object of the present invention is to provide a method for preparing an oral solid preparation containing amorphous solifenacin having excellent stability of an active ingredient.
  • Amorphous solifenacin or a pharmaceutically acceptable salt thereof provides a solid preparation for oral administration comprising a stabilizer.
  • One aspect of the present invention provides at least 90% amorphous solifenacin or a pharmaceutically acceptable salt thereof; And a stabilizer selected from the group consisting of alkane celluloses, antioxidants, and any combination thereof.
  • Solifenacin or a pharmaceutically acceptable salt thereof And spray drying a mixed solution of a stabilizer selected from the group consisting of alkancelluloses, antioxidants, and any combination thereof to produce amorphous solifenacin powder.
  • the stabilizer provides a method for producing an oral solid preparation according to an aspect of the present invention, which is selected from alkancelluloses, neutral antioxidants, and any combination thereof.
  • the amorphous solvenacin-containing oral solid preparation contains hypromellose or hydroxypropyl cellulose, which not only maintains its amorphous form over time, but also significantly lowers the generation of flexible substances.
  • the solid preparation has high stability over time of the active ingredient.
  • the oral solid preparation may enable effective oral administration of amorphous solifenacin.
  • 1 to 4 are XRD graphs after four weeks of storage of a solid preparation for oral solifenacin according to Examples 1 to 4 of the present invention at 60 ° C. under severe storage conditions of HDPE bottles.
  • 5 to 7 are XRD graphs after 4 weeks of storage of a solid preparation for oral solifenacin according to Comparative Examples 1 to 3 at 60 ° C. under severe storage conditions of HDPE bottles.
  • the present invention provides amorphous solifenacin or a pharmaceutically acceptable salt thereof; And it provides a solid preparation for oral administration comprising a stabilizer.
  • the invention provides amorphous solifenacin or a pharmaceutically acceptable salt thereof; And stabilizers,
  • the stabilizer provides a solid dosage form for oral administration, which is selected from the group consisting of alkancelluloses, antioxidants, and any combination thereof.
  • the amorphous solifenacin or the pharmaceutically acceptable salt thereof is 90% by weight or more based on the total weight of the solifenacin or the pharmaceutically acceptable salt thereof,
  • the stabilizer provides a solid dosage form for oral administration that is selected from the group consisting of alkancelluloses, antioxidants, and any combination thereof.
  • the alkane cellulose may be selected from the group consisting of hypromellose, hydroxypropyl cellulose, hydroxypropyl ethyl cellulose, methyl cellulose, ethyl cellulose, phthalic acid hydroxypropyl cellulose, and any combination thereof. .
  • the alkane cellulose may be hypromellose, hydroxypropyl cellulose or a combination thereof.
  • the antioxidant may be a neutral antioxidant.
  • the neutral antioxidant may be an antioxidant including a phenol derivative. More specifically, the neutral antioxidant may be selected from butylhydroxytoluene, butylhydroxyanisole, propyl gallate, tocopherol, and any combination thereof. In one embodiment, the neutral antioxidant can be selected from butylhydroxytoluene, butylhydroxyanisole, propyl gallic acid and any combination thereof.
  • compositions of solifenacin include acid addition salts or quaternary ammonium salts, and the acid addition salts include inorganic or organic acid salts.
  • the inorganic acid salts include, but are not limited to, hydrochloride, hydrobromide, hydroiodide, sulfate, nitrate, phosphate, and the like.
  • the organic acid salts are formate, acetate, propionate, oxalate, malonate, succinate, fumarate, maleate, lactate, malate, citrate, tartarate, carbonate, picrate, methanesulfonate, ethane Sulfonate, glutamate, and the like, but are not limited thereto.
  • the pharmaceutically acceptable salt of solifenacin is solifenacin succinate.
  • stabilization of an active ingredient means inhibiting any change in the active ingredient by increasing the stability of the active ingredient, and includes inhibiting the change in the crystal form of the active ingredient or the formation of a flexible substance.
  • stabilizer means any pharmaceutically acceptable additive that can increase the stability of the active ingredient and includes amorphous crystalline inhibitors and antioxidants of the active ingredient.
  • stabilizer means any pharmaceutically acceptable additive that is effective in inhibiting the oxidation of the active ingredient.
  • the stabilizer is hypromellose, hydroxypropyl cellulose; And antioxidants selected from butylhydroxytoluene, butylhydroxyanisole, and combinations thereof.
  • the present inventors have diligently studied for the development of a solid formulation having high stability of amorphous solifenacin, and when the solid formulation is prepared by containing alkane cellulose such as hypromellose or hydroxypropyl cellulose, Compared with other polymers, it is possible to block the amorphous crystallization remarkably, and to prepare a solid preparation by containing an antioxidant such as butylhydroxytoluene, butylhydroxyanisole, propyl gallate, or tocopherol It has been found that the increase in lead can be significantly reduced compared to other antioxidants.
  • the hypromellose may be, but is not limited to, hypromellose having 16.5 to 30% of methoxyl groups and 4 to 32% of hydroxypropoxyl groups.
  • the hypromellose may be hypromellose 1828, hypromellose 2208, hypromellose 2906, or hypromellose 2910.
  • the alkane cellulose may be present in an amount of 0.1 to 5.0 parts by weight, more specifically 0.5 to 3.0 parts by weight with respect to 1 part by weight of the amorphous solifenacin or a pharmaceutically acceptable salt thereof. If the content does not reach the content, the crystallization blocking effect of suppressing the crystallization of amorphous solifenacin may not be sufficiently exhibited. If the content exceeds the content, the viscosity may be high, which may cause a problem in process setting.
  • the antioxidant selected from butylhydroxytoluene, butylhydroxyanisole, propyl gallate, tocopherol and any combination thereof may be used in an amount of 0.005 to 1.0 weight based on 1 part by weight of the amorphous solifenacin or its pharmaceutically acceptable salts. Parts, more specifically, 0.01 to 0.1 parts by weight. If the content is less than the stabilization effect may not appear sufficiently, if the content is exceeded, the degree of improvement of the stabilization effect may be very insignificant.
  • the oral solid preparation may be formulated, for example, as pellets, capsules, tablets, powders, granules, or dry syrups, but is not limited thereto. More specifically, the oral solid preparation may be in the form of a capsule or tablet. When the composite formulation of the present invention is a capsule, the capsule may be in the form of a powder, granules, tablets, dry syrup, pellets and the like therein.
  • the amorphous solifenacin or a pharmaceutically acceptable salt thereof, and the stabilizer may be included in the oral solid preparation in the form of a spray-dried powder of their mixed solution.
  • the "in the form of a spray-dried powder may be included in the oral solid preparation" is a spray-dried powder is included as it is, filled into a capsule, or included in the form of granules prepared using a spray-dried powder, It is interpreted to mean that it is included as a state in which the property of a powder is not maintained as it is by an additional process, such as tableting and tableting it into the granule.
  • the solvent for preparing the mixed solution may be used amorphous solifenacin or a pharmaceutically acceptable salt thereof, and any pharmaceutically acceptable solvent that can dissolve all of the stabilizers, for example ethanol and It is a mixed solvent of water.
  • the mixed solvent is a mixture of ethanol and purified water, more specifically, the mixture of ethanol and purified water may be a volume ratio of ethanol: water of 1 to 9: 9 to 1, for example, the volume ratio of ethanol: water About 5: 5, but is not limited thereto.
  • the solid preparation is a tablet, may be a tablet by a direct compression method for tableting the raw material mixture, or may be a tablet by a granulation compression method for tableting after granulation of the raw material mixture. In one embodiment, the tablet may be a tablet by direct compression method.
  • the pharmaceutically acceptable additives included in the oral solid preparations according to the present invention may be any additives that the oral solid preparations typically include, for example, diluents, binders, disintegrants, glidants, and these It can be selected from the group consisting of any combination of.
  • the diluent is used for increasing and may be selected from the group consisting of lactose or its hydrate, microcrystalline cellulose, mannitol, starch, sucrose, lactose, sorbitol, xylitol, glucose, calcium dihydrogen phosphate, and any combination thereof. It is not limited to this.
  • the binder may be selected from the group consisting of hydroxypropyl cellulose, polyvinylpyrrolidone, copovidone, macrogol, hard silicic anhydride, and any combination thereof, but is not limited thereto.
  • the disintegrants include crospovidone, croscarmellose sodium, sodium starch glycolate, low-substituted hydroxypropyl cellulose, starch, alginic acid or its sodium salt, carboxymethylcellulose sodium, microcrystalline cellulose, powdered cellulose, pregelatinized starch, And any combination thereof, but is not limited thereto.
  • the glidants include stearic acid, stearic acid metal salts (e.g. calcium stearate, magnesium stearate, etc.), talc, colloidal silica, sucrose fatty acid esters, hydrogenated vegetable oils, waxes, glyceryl fatty acid esters, glycerol dibehenate, And it may be selected from the group consisting of any combination thereof, but is not limited thereto.
  • the oral solid preparation may contain about 2.5 to 10 mg of free active solvenacin or its pharmaceutically acceptable salt per unit dosage form, more specifically about 5 to 10 mg. It may contain mg.
  • the oral solid preparation may be administered to a mammal, including a person having any indication of solifenacin or a pharmaceutically acceptable salt thereof.
  • the oral solid preparations can be used for the treatment or prevention of any disease that is effective in good selective antagonistic action on muscarinic M 3 receptors.
  • the diseases include urinary diseases such as neuronal urinary, neurogenic bladder, enuresis, irritable bladder, bladder spasm, or chronic cystitis; Respiratory diseases such as, but not limited to, sex obstructive pulmonary disease, chronic bronchitis, asthma, or rhinitis.
  • the oral solid preparations can be used to treat overactive bladder.
  • Solifenacin or a pharmaceutically acceptable salt thereof And spray drying a mixed solution of a stabilizer selected from the group consisting of alkancelluloses, antioxidants, and any combination thereof to produce amorphous solifenacin powder.
  • the stabilizer is hypromellose, hydroxypropyl cellulose; Antioxidants selected from butylhydroxytoluene, butylhydroxyanisole, propyl gallic acid and any combination thereof; And it is selected from any combination thereof, provides a method for producing an oral solid preparation according to one aspect of the present invention.
  • the step of solidifying may be performed according to any method known in the art of formulating a solid solvenacin powder as the raw material, into a solid preparation, for example pellets, capsules It may be carried out according to any known method for formulating into a formulation, tablet, powder, granule, or dry syrup.
  • the step of solidifying may be a method of mixing the amorphous solifenacin powder with a pharmaceutically acceptable additive and then preparing a tablet by tableting.
  • the tableting may be an indirect tableting method of preparing and then granulating the granules, or may be a direct tableting method of mixing and then tableting with other pharmaceutically acceptable additives without preparing the granules.
  • the tableting is a direct tableting method.
  • Example 1 amorphous Solifena Succinate Manufacture of tablets
  • solvenasin succinate, hypromellose and butylhydroxytoluene dissolved in a mixture of ethanol and purified water (ethanol: water 5: 5) by spray-drying the amorphous solvena Succinate spray dried powder was obtained. It was dried at 60 ° C., sieved to 30 mesh, and then all the remaining ingredients were added to prepare a mixture. Then, the mixture was compressed into tablets using a rotary punching machine (GRC-18; Sejong Machinery, Korea) using a round punch having a diameter of 8.0 mm to prepare solifenacin succinate tablets having a hardness of about 5 to 12 kp. Then, the solvena succinate succinate tablet prepared as described above was coated with a solution in which Opadry Pink was dispersed in purified water.
  • Example 2 to 8 amorphous Solifena Succinate Manufacture of tablets
  • solvena succinate succinate tablets were prepared in the same manner as in Example 1 with the contents of Examples 2 to 8 shown in Table 1.
  • butylhydroxyanisole was used instead of butylhydroxytoluene
  • gallic acid propyl was used instead of butylhydroxytoluene.
  • UV absorbance photometer (wavelength: 210 nm)
  • Phosphate buffer (pH 6.0): Dissolve 8.7 g of anhydrous dipotassium hydrogen phosphate in 1 L of water, and add phosphoric acid to pH 6.0.
  • Examples 1 to 8 are different from those in which the amount of the flexible substance generated over time includes butylhydroxytoluene, butylhydroxyanisole, or gallic acid propyl as an antioxidant. It was found to be significantly less compared to Comparative Examples 4-7, including antioxidants.
  • amorphous solifenacin succinate spray dried powders obtained in Examples 1 to 4 and Comparative Examples 1 to 3 were stored under the following severe conditions, and then crystalline changes were analyzed by XRD.

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  • Chemical & Material Sciences (AREA)
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  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
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  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
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  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Un aspect de la présente invention concerne une préparation solide destinée à être administrée par voie orale, contenant de la solifénacine amorphe ou un sel pharmaceutiquement acceptable de celle-ci ; et un agent stabilisant choisi dans le groupe constitué par des alcanes de celluloses, des antioxydants, et une combinaison quelconque de ceux-ci.
PCT/KR2016/012490 2015-11-11 2016-11-02 Préparation solide contenant de la solifénacine amorphe à usage oral et son procédé de préparation WO2017082577A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
MX2018005848A MX2018005848A (es) 2015-11-11 2016-11-02 Preparacion solida que contiene solifenacina amorfa para uso oral y metodo de preparacion de la misma.
BR112018009413A BR112018009413A2 (pt) 2015-11-11 2016-11-02 formulação oral sólida e método para preparar a formulação oral sólida
EA201890896A EA201890896A1 (ru) 2015-11-11 2016-11-02 Твердый препарат для перорального применения, содержащий аморфный солифенацин, и способ его получения
CN201680065960.3A CN108348617A (zh) 2015-11-11 2016-11-02 用于口服用途的含有无定形索非那新的固体制剂及其制备方法
PH12018500980A PH12018500980A1 (en) 2015-11-11 2018-05-07 Amorphous solifenacin-containing solid preparation for oral use and preparation method therefor

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2015-0158108 2015-11-11
KR1020150158108A KR20170055211A (ko) 2015-11-11 2015-11-11 무정형 솔리페나신 함유 경구용 고형제제 및 그 제조방법

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KR (1) KR20170055211A (fr)
CN (1) CN108348617A (fr)
BR (1) BR112018009413A2 (fr)
EA (1) EA201890896A1 (fr)
MX (1) MX2018005848A (fr)
PH (1) PH12018500980A1 (fr)
WO (1) WO2017082577A1 (fr)

Families Citing this family (4)

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Publication number Priority date Publication date Assignee Title
KR20180003340A (ko) * 2016-06-30 2018-01-09 한미약품 주식회사 무정형 솔리페나신 함유 경구용 고형제제 및 그 제조방법
KR20200078121A (ko) 2018-12-21 2020-07-01 한미약품 주식회사 탐수로신 및 솔리페나신을 포함하는 경구용 복합제제 및 그 제조방법
KR20200121183A (ko) 2019-04-15 2020-10-23 한미약품 주식회사 탐스로신 및 솔리페나신을 포함하는 복합제제 및 그 제조방법
KR20210114271A (ko) 2020-03-10 2021-09-23 주식회사 종근당 솔리페나신 또는 이의 약제학적으로 허용가능한 염을 함유하는 약제학적 조성물

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100137358A1 (en) * 1996-11-05 2010-06-03 Dr. Reddy's Laboratories Ltd. Solifenacin compositions
US20100273825A1 (en) * 2009-03-30 2010-10-28 Astellas Pharma Inc. Solid pharmaceutical composition containing solifenacin amorphous form
KR20150092385A (ko) * 2014-02-03 2015-08-13 씨제이헬스케어 주식회사 솔리페나신을 포함하는 안정한 제제 및 이의 제조방법
KR20150102852A (ko) * 2014-02-28 2015-09-08 대원제약주식회사 무정형 솔리페나신 또는 그의 염을 포함하는 안정성이 증가된 고체분산체 조성물 및 그 제조방법
WO2015170237A1 (fr) * 2014-05-05 2015-11-12 Torrent Pharmaceuticals Limited Composition de solifénacine stable

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100137358A1 (en) * 1996-11-05 2010-06-03 Dr. Reddy's Laboratories Ltd. Solifenacin compositions
US20100273825A1 (en) * 2009-03-30 2010-10-28 Astellas Pharma Inc. Solid pharmaceutical composition containing solifenacin amorphous form
KR20150092385A (ko) * 2014-02-03 2015-08-13 씨제이헬스케어 주식회사 솔리페나신을 포함하는 안정한 제제 및 이의 제조방법
KR20150102852A (ko) * 2014-02-28 2015-09-08 대원제약주식회사 무정형 솔리페나신 또는 그의 염을 포함하는 안정성이 증가된 고체분산체 조성물 및 그 제조방법
WO2015170237A1 (fr) * 2014-05-05 2015-11-12 Torrent Pharmaceuticals Limited Composition de solifénacine stable

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BR112018009413A2 (pt) 2018-12-04
PH12018500980A1 (en) 2019-01-28
KR20170055211A (ko) 2017-05-19
EA201890896A1 (ru) 2018-10-31
CN108348617A (zh) 2018-07-31
MX2018005848A (es) 2019-07-18

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