WO2005009474A1 - Agent pharmaceutique sec pour sirop, difficilement soluble dans l'eau - Google Patents

Agent pharmaceutique sec pour sirop, difficilement soluble dans l'eau Download PDF

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Publication number
WO2005009474A1
WO2005009474A1 PCT/JP2004/010386 JP2004010386W WO2005009474A1 WO 2005009474 A1 WO2005009474 A1 WO 2005009474A1 JP 2004010386 W JP2004010386 W JP 2004010386W WO 2005009474 A1 WO2005009474 A1 WO 2005009474A1
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WO
WIPO (PCT)
Prior art keywords
dry syrup
water
soluble drug
poorly water
aqueous solution
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Application number
PCT/JP2004/010386
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English (en)
Japanese (ja)
Inventor
Toshitada Toyoda
Yoshitsugu Muguruma
Yoshitaka Tomoda
Original Assignee
Shionogi & 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 Shionogi & Co., Ltd. filed Critical Shionogi & Co., Ltd.
Priority to JP2005512015A priority Critical patent/JP4640821B2/ja
Publication of WO2005009474A1 publication Critical patent/WO2005009474A1/fr

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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
    • A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
    • A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches

Definitions

  • the present invention relates to a dry syrup containing a poorly water-soluble drug, more specifically, a hydroxy syrup containing at least a poorly water-soluble drug and a 2% (w / v)% aqueous solution at 20 ° C having a viscosity of less than 3. OmPa's.
  • the present invention relates to a dry syrup containing not less than 0.5 (w / w)% of cypropylcellulose. Background art
  • Pharmaceutical dosage forms include various forms such as tablets, granules, capsules and the like.
  • dry syrups which are one of the pharmaceutical dosage forms, are equivalent to "preparations to be used by dissolving or suspending before use”. Dry syrup is easy to take, especially for children who dislike the drug and elderly people who have difficulty swallowing. Further, since the dry syrup is in the form of powder or granules, it has an advantage that it can be easily packaged and weighed, and is convenient to carry.
  • Patent Document 1 discloses a fast dissolving oral dosage form containing diclofenac sodium, mannitol and polybierpyrrolidone
  • Patent Document 2 describes a dry syrup containing faropenem sodium, sucrose, hydroxypropylcellulose, etc.
  • Power Patent Document 3 discloses a dry syrup containing ampicillin, sugar and 0.3 (wZw)% hydroxypropylcellulose.
  • all of the drugs used in the above formulations have relatively high water solubility, with a water solubility at 20 ° C of 100 ppm or more.
  • Patent Document 4 discloses terfenadine, sucrose, and HPC-SL (a 2% (w / v)% aqueous solution at 20 ° C) with water solubility of less than 100 ppm. Hydroxypropylcellulose having a viscosity of 3.0-5.9 mPa's] is disclosed, but the presence or absence of suspended matter and the addition of water to water after stirring are disclosed. The presence or absence of the defoaming property is disclosed.
  • Patent Document 1 JP-T-2000-508649
  • Patent Document 2 International Publication No. 01/26691 pamphlet
  • Patent Document 3 JP-A-54-32615
  • Patent Document 4 JP-A-6-15712
  • the present inventors have conducted intensive studies and found that even in the case of poorly water-soluble drugs, the viscosity of a 2% (w / v)% aqueous solution in a dry syrup is less than 3.OmPa's at 20 ° C. It has been found that by including hydroxypropyl cellulose, a dry syrup having excellent physical properties can be obtained. That is, it has been found that the dry syrup preparation of the present invention exhibits excellent sedimentation when put into water. In addition, the dry syrup preparation of the present invention exhibited excellent dispersibility and redispersibility, did not produce suspended matter, and was found to have improved defoaming properties, and thus completed the present invention described below.
  • At least 0.5% (w / w)% of a poorly water-soluble drug and hydroxypropylcellulose whose viscosity of a 2 (w / v)% aqueous solution at 20 ° C is less than 3.0 mPa's is contained. , Dry syrup.
  • the present invention provides, as a first embodiment, at least a poorly water-soluble drug and a hydroxypropylcellulose having a viscosity of a 2 (w / v)% aqueous solution at 20 ° C of less than 3. ) Provide dry syrup containing at least%.
  • the dry syrup preparation of the present invention becomes a uniform dispersion liquid when water is used.
  • Homogeneous dispersion means a formulation with the following physical properties:
  • the poorly water-soluble drug which is an active ingredient of the dry syrup preparation of the present invention is a drug, a quasi-drug
  • the water solubility at 20 ° C. is preferably 1000 Oppm, more preferably 1000 ppm, particularly preferably 100 ppm or less.
  • the amount of the poorly water-soluble drug is not particularly limited, as long as the relative mixing ratio of the drug does not decrease. Specifically, 0.01 to 50.0 (w / w)%, preferably 0.1 to 10.0 (w / w)%, more preferably 0.5 to 5.0 (w / w) / w)%, particularly preferably 0.5-3.0 (w / w)%. If the amount is larger than this, the drug may not be sufficiently suspended. If the amount is smaller, production may be difficult in terms of content uniformity.
  • the hydroxypropyl cellulose contained in the dry syrup of the present invention also functions as a suspending agent for stabilizing the suspendability of the drug and also as a binder for the dry syrup.
  • the viscosity of a 2 (wZv)% aqueous solution at 20 ° C measured by a B-type viscometer is less than 3.
  • OmPa's hereinafter abbreviated as HPC-C.
  • hydroxypropylcellulose is sold as a commercial product as long as the viscosity of an aqueous solution of 2 (w / v)% hydroxypropylcellulose is less than 3.OmPa's. It may be a mixture of one or more of various grades of hydroxypropylcellulose.
  • the amount of the hydroxypropyl cellulose is 0.5 (w / w)% or more in the preparation, preferably 0.5 to 10.0 (w / w)%, more preferably 0.5 to 5.0 (w / w). / w) ⁇ 0.5-1.0 (w / w) Q / o is particularly preferred. If the amount is less than this, physical properties such as uniform dispersibility cannot be improved.
  • Carbohydrates contained in the dry syrup preparation of the present invention include sugars and sugar alcohols, for example, sucrose, glucose, D-mannitol, powdered reduced maltose starch syrup, maltitol, erythritolone, D-sonorebitonere, maltose, Lactose, starch and starch derivatives, mannose, sonorebose, xylose, trehalose, hunolectose, dextran, punorellan, dextrin, cyclodextrin, soluble starch, hydroxyethyl starch, carboxymethinoresenorelose_Na, mannitolenole, rectitonoll
  • sugars and sugar alcohols for example, sucrose, glucose, D-mannitol, powdered reduced maltose starch syrup, maltitol, erythritolone, D-sonorebitonere, maltose, Lactose, star
  • sucrose is preferred.
  • the amount of the carbohydrate in the preparation is 20.0 (w / w)% or more, preferably 50.0 to 99.4 (w / w) o / 0 , more preferably 80. 0 to 99.0 (w / w). %, Particularly preferably 90.0-99.0 (w / w)%. If the amount is less than this, it may not be possible to sufficiently maintain the shape of granules.
  • the dry syrup preparation of the present invention contains 0.01-50.0% (w / w)% of poorly water-soluble drug and 0.5% (w / w)% or more of HPC-C, Sucrose is at least 20.0 (w / w)%, preferably 0.1-10.0 (w / w)% of poorly water-soluble drug, 0.5-10.0 (w / w)% of HPC-C, Saccharose is 50-99-4 (w / w)%, more preferably poorly water-soluble drug is 0.5-5.0 (w / w)%, UPC-C power is 0.5-5.0 (w / w) %, Sucrose power 80.0-99.0 (w / w)%, particularly preferably 0.5-3.0 (w / w)% for poorly water-soluble drugs, 0.5-1.0 (w / w)% for HPC-C, Saccharose is 90.0-99.0 (wZw)%.
  • the dry syrup of the present invention may contain pharmaceutically acceptable additives other than those described above.
  • Additives include sweeteners, lubricants, suspending agents, pH adjusters, preservatives, flavors and the like.
  • Lubricants include those called fillers, adsorbents or fluidizers, for example, At least one type is selected from silicon dioxide, light caffeic anhydride, sucrose fatty acid ester, magnesium stearate and the like.
  • Sweeteners usually include carbohydrates or non-sugars, but here, non-sugar natural or synthetic sweeteners, such as aspartame, glycyrrhizic acid and salts thereof, and saccharin And its salts, stevia and its salts, sucralose, acesulfame potassium, and the like.
  • non-sugar natural or synthetic sweeteners such as aspartame, glycyrrhizic acid and salts thereof, and saccharin And its salts, stevia and its salts, sucralose, acesulfame potassium, and the like.
  • pH adjusters include those called acids, bases or buffers, such as hydrochloric acid, dilute hydrochloric acid, sulfuric acid, adipic acid and its salts, citric acid and its salts, dalconic acid and its salts, succinic acid and its salts Ascorbic acid and its salts, glacial acetic acid and its salts, acetic acid and its salts, tartaric acid and its salts, fumaric acid and its salts, maleic acid and its salts, lactic acid and its salts, malic acid and its salts, phosphoric acid and
  • the salt, glycine, sodium hydrogencarbonate, sodium carbonate, sodium hydroxide, magnesium hydroxide and the like are selected from at least one kind.
  • Preservatives include those referred to as stabilizing (stabilizing) agents, such as benzoic acid and its salts, etedic acid and its salts, salicylic acid and its salts, dibutylhydroxytoluene, sorbic acid and its salts, sodium acetic acid sodium salt, At least one kind is selected from paraoxybenzoic acid and salts thereof.
  • Flavors include those called fragrances, for example, orange essence, orange oil, caramenole, camphor, queich oil, spearmint oil, strawberry essence, chocolate essence, cherry flavor, spruce oil, pine oil, heart oil , Vanilla flavor, bitter essence, fruit flavor, peppermint essence, mixed flavor, mint flavor, menthol, lemon powder, lemon oil, rose oil, etc.
  • the dry syrup preparation of the present invention may contain a surfactant and an antifoaming agent.
  • a surfactant as described above.
  • examples of such surfactants include sucrose fatty acid esters, sorbitan fatty acid esters, polyoxyethylene hydrogenated castor oil, polyoxyethylene sorbitan fatty acid esters, and sodium lauryl sulfate.
  • the dry syrup does not contain an antifoaming agent as described above.
  • antifoaming agents examples include silicone resin, silicone resin emulsion, silicone antifoaming agent, silicone oil, sucrose fatty acid ester, glycerin fatty acid ester, dimethylpolysiloxane, dimethylpolysiloxane; silicon dioxide mixture; 40, sorbitan fatty acid esters, sorbitan trioleate, polyoxyethylene sorbitan fatty acid esters.
  • the particle size of the dry syrup is not particularly limited, but is generally the particle size range of powders, fine granules, and granules according to the Japanese Pharmacopoeia Fourteenth Edition.
  • the dry syrup of the present invention is produced by a usual method for producing powders, granules and fine granules.
  • a stirring granulation method for producing powders, granules and fine granules.
  • an extrusion granulation method for extrusion granulation method
  • a fluidized bed granulation method for granulating powders
  • a tumbling granulation method for granulating powders, granules and fine granules.
  • a crushing granulation method for example, there are a stirring granulation method, an extrusion granulation method, a fluidized bed granulation method, a tumbling granulation method, a crushing granulator, a spray granulation method, a crushing granulator, and the like.
  • the agitation granulation method will be briefly described.
  • a predetermined amount of the poorly water-soluble drug and saccharide are weighed, sieved with a sieve having an opening of 425 ⁇ m, and the powder that has passed through the sieve is placed in a stirring granulator and mixed.
  • a predetermined amount of a binder is added, and the mixture is granulated for a certain period of time. After that, it is dried with a fluidized bed granulator and sized using a basket with an opening of 1038 ⁇ . If necessary, fines can be removed with a classifier using a sieve with an aperture of 154 ⁇ .
  • An appropriate additive is blended with the obtained granules and mixed to obtain a target dry syrup.
  • some or all of the additives may be sieved simultaneously with the first poorly water-soluble drug or carbohydrate.
  • the extrusion granulation method can be performed in the same manner as the stirring granulation method, except that the drug substance, the additives, and the like are mixed and granulated by the stirring granulator, and then the extrusion granulator is used.
  • the extrusion granulator for example, a DGL1 type dome gran (Fuji Padal Co., Ltd., hole diameter: 0.5 mm) and a cylindrical granulator (Yamada Iron Works Co., Ltd., hole diameter: 0.53 mm) can be used.
  • Fluidized bed granulation can be performed in the same manner except that a fluidized bed granulator is used instead of the stirred granulator used in the above stirred granulation method.
  • a fluidized-bed granulator for example, a WSG-5 type granulation dryer (manufactured by Dai-J11 Hara Seisakusho) can be used.
  • the present invention provides a hydroxypropylcellulose having a 2 (wZv)% aqueous solution viscosity of less than 3. And a dispersion in which the poorly water-soluble drug is uniformly dispersed in water.
  • the dispersion of the present invention can be obtained by putting the dry syrup preparation of the present invention into an appropriate amount of water and stirring.
  • a dry syrup is produced by combining a poorly water-soluble drug and hydroxypropylcellulose having a viscosity of a 2 (wZv)% aqueous solution at 20 ° C of less than 3.OmPa's.
  • the present invention provides a method for preventing the formation of suspended matter on a dispersion when a dry syrup preparation of a poorly water-soluble drug is added to water and improving the defoaming property.
  • the present invention will be described in more detail with reference to Examples and Comparative Examples, but the present invention is not limited thereto.
  • the power S of using ethenzamide and sulfamethoxazole as poorly water-soluble drugs, and their water solubility are all less than 100 ppm.
  • a dry syrup having the following composition (w / w)% was produced together with the comparative example preparation.
  • Polysorbate 80 Polyoxyethylene sorbitan fatty acid ester Based on Table 1 above, the amount is appropriately converted to the amount charged and weighed. The drug used was ethenzamide listed in the Japanese Pharmacopoeia of the 14th Edition.
  • Example 1 20 g of ethenzamide and 1958 g of sucrose are weighed and sieved with a sieve having openings. The powder passed through the sieve and passed through the sieve was put into a stirring granulator (10-type high-speed mixer, manufactured by Fukae Patetech Co., Ltd./Agitator: 30 (kpm, chopper: 2500i "pm)) and mixed for 1 minute.
  • a stirring granulator 10-type high-speed mixer, manufactured by Fukae Patetech Co., Ltd./Agitator: 30 (kpm, chopper: 2500i "pm)
  • Comparative Example 1 a predetermined amount of ethenzamide and sucrose were weighed, sieved with a sieve having an opening of 425 ⁇ m, and the powder passed through the sieve was produced in the same manner as in Example 1. For granulation, 120 g of purified water was used. Comparative Example 24 is produced in the same manner as in Example 1, except that polysorbate 80 and the silicone resin are used by dissolving or suspending them in purified water, or by adsorbing on water-containing silicon dioxide and powdering.
  • Example 1 20 g of ethenzamide and 1911 g of sucrose were weighed, sieved with a sieve having an aperture of 425 ⁇ , and the powder passed through the sieve was stirred with a stirring granulator (type 10 high-speed mixer, manufactured by Fukae Patetech Co., Ltd.). / Agitator: 30 (kpm, chopper: 2500i "pm) and mixed for 1 minute. Then, 120 g of 10 (w / v) aqueous solution of HPC-C was poured, and the mixture was granulated for 3 minutes.
  • a stirring granulator type 10 high-speed mixer, manufactured by Fukae Patetech Co., Ltd.
  • / Agitator 30 (kpm, chopper: 2500i "pm) and mixed for 1 minute.
  • 120 g of 10 (w / v) aqueous solution of HPC-C was poured, and the mixture was granulated for 3 minutes.
  • Comparative Example 1 a predetermined amount of ethenzamide and sucrose was weighed, and a sieve having a mesh size of 425 ⁇ m was used. The powder passed through the sieve was produced in the same manner as in Example 1, but 120 g of purified water was used for pouring the liquid during granulation. Comparative Examples 2 to 4 are produced in the same manner as in Example 1, except that polysorbate 80 and a silicone resin are dissolved or suspended in purified water, adsorbed on hydrated silicon dioxide, and used in powder form.
  • Example 1 50 g of ethenzamide and 4895 g of white sugar were weighed, sieved with a sieve having an opening of 425 xm, and the powder passed through the sieve was subjected to a fluidized bed granulator (WSG-5 granulator / dryer, manufactured by Okawara Was mixed for 5 minutes. Thereafter, 1500 g of an aqueous solution of 2 (wZv)% HPC_C was sprayed (spray speed: 30 g / min, spray pressure: 0.15 MPa). 0 After that, the process was finished when the product temperature reached 45 ° C.
  • WSG-5 granulator / dryer manufactured by Okawara was mixed for 5 minutes.
  • 1500 g of an aqueous solution of 2 (wZv)% HPC_C was sprayed (spray speed: 30 g / min, spray pressure: 0.15 MPa).
  • a basket having a mesh size of 1038 xm was used, and sized using a sizing machine (P-3 type powder mill). Thereafter, if necessary, a wire mesh having a mesh size of 154 xm was used, and the fine powder was removed with a classifier (TMC-50-2S vibrating sieve, manufactured by Tokuju Corp.).
  • TMC-50-2S vibrating sieve manufactured by Tokuju Corp.
  • the obtained granules (about 4776 g) were mixed with 24 g of hydrous silicon dioxide calculated from Table 1, and mixed with a mixer (22L V-type mixer) to obtain dry syrup IJ.
  • Comparative Example 1 the Etenzamido and white sugar were weighed predetermined amounts, sieved mesh opening with a sieve of 425 beta m, but to produce a powder that passed through the sieve in the same manner as in Example 1, 1500g of purified water was used for liquid injection during granulation. Comparative Examples 2 to 4 are produced in the same manner as in Example 1, except that polysorbate 80 and a silicone resin are dissolved or suspended in purified water, adsorbed on hydrated silicon dioxide, and used in powder form.
  • the stoppered measuring cylinder used for evaluation of dispersibility was left at room temperature for one day. After that, it was judged by the same evaluation method as the dispersibility in water.
  • the lid of the stoppered measuring cylinder was removed and visually observed from above. The presence / absence of suspended matter was judged as X if there was no suspended matter within 1 minute, and if there was no suspended matter within 10 minutes.
  • ⁇ improved defoaming property '' means that bubbles can be reduced within 1 minute and the water surface can be seen, but preferably within 50 seconds, more preferably within 40 seconds, and the water surface can be reduced. I just need to see.
  • Comparative Example 1 did not contain a suspending agent, and all of the formulations of Comparative Examples 5-7 contained a suspending agent different from HPC-C. This indicates that only HPC-C is essential for improving the uniform dispersibility in water of the dry syrup.
  • hydroxypyrucellulose has a viscosity of less than 3.OmPa's in a 2% (w / v)% aqueous solution at 20 ° C (B-type viscometer) when HPC_B [20 ° C is used. C 2 (w / v). /.
  • the viscosity of the aqueous solution was 3.0-5.9 mPa's (B-type viscometer)] and the HPC-A [the viscosity of a 2 (wZv)% aqueous solution at 20 ° C was 6.0-10 OmPa's (B-type viscometer)] was used. .
  • Comparative Examples 10 and 11 and Example 1 The uniform dispersibility of Comparative Examples 10 and 11 and Example 1 was evaluated by the evaluation method in Test Example 1.
  • the dispersibility refers to the number of inversions of the stoppered graduated cylinder until the preparation is dispersed, and the defoaming property refers to the time until the foam disappears.
  • the results obtained are shown in Table 8 below.
  • each preparation having the compounding ratio shown in Table 9 was produced.
  • As a drug use sulfamethoxazole listed in the 14th Revised Japanese Pharmacopoeia in place of ethenzamide.
  • the dry syrup preparation of the present invention is easy to take even for children who dislike the medicine and for the elderly who have difficulty swallowing, and is easy to package and weigh. Furthermore, it is convenient to carry.

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Abstract

L'invention concerne un agent pharmaceutique sec pour sirop, difficilement soluble dans l'eau. Ledit agent est produit à partir d'hydroxypropylcellulose dont la viscosité mesurée pour une solution aqueuse à 2 % p/v à 20 °C est inférieure à 3,0 mPa.s.
PCT/JP2004/010386 2003-07-24 2004-07-22 Agent pharmaceutique sec pour sirop, difficilement soluble dans l'eau WO2005009474A1 (fr)

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JP2005512015A JP4640821B2 (ja) 2003-07-24 2004-07-22 難水溶性薬物を含むドライシロップ剤

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JP2003-278747 2003-07-24

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Cited By (13)

* Cited by examiner, † Cited by third party
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JP2005162696A (ja) * 2003-12-04 2005-06-23 Nichiko Pharmaceutical Co Ltd 溶出性に優れたセフジトレンピボキシル製剤
JP2007269783A (ja) * 2006-03-06 2007-10-18 Toyama Chem Co Ltd トシル酸トスフロキサシンを含有する粒状固形製剤
JP2010013357A (ja) * 2008-07-01 2010-01-21 Takada Seiyaku Kk 高含量ｌ−カルボシステインドライシロップ剤
EP2233004A2 (fr) 2007-09-12 2010-09-29 Bayer CropScience AG Traitement après récolte
WO2010149369A1 (fr) 2009-06-24 2010-12-29 Bayer Cropscience Ag Combinaisons de levure à activité fongicide et de fongicides
WO2010149370A1 (fr) 2009-06-24 2010-12-29 Bayer Cropscience Ag Compositions d'agents de lutte biologique et d'insecticides
WO2011128297A2 (fr) 2010-04-14 2011-10-20 Bayer Cropscience Ag Combinaisons de composés actifs
WO2011151383A1 (fr) 2010-06-03 2011-12-08 Bayer Cropscience Ag O-cyclopropylcyclohexyl-carboxanilides et leur utilisation en tant que fongicides
EP2454939A1 (fr) 2010-11-18 2012-05-23 Bayer CropScience AG Traitement post-récolte
WO2012102538A2 (fr) * 2011-01-28 2012-08-02 제이더블유중외제약 주식회사 Composition de sirop sec
WO2014111254A1 (fr) 2013-01-15 2014-07-24 Astellas Pharma Europe Ltd Composition de composés de tiacumicine
WO2020004456A1 (fr) 2018-06-27 2020-01-02 第一三共株式会社 Préparation granulaire contenant un dérivé de diamine
WO2020204001A1 (fr) * 2019-03-29 2020-10-08 富士フイルム株式会社 Procédé de production d'une composition de suspension aqueuse et composition de suspension aqueuse

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WO2002043704A1 (fr) * 2000-12-01 2002-06-06 Kyowa Hakko Kogyo Co., Ltd. Composition a solubilite ou absorbabilite orale amelioree
JP2003026676A (ja) * 2000-12-11 2003-01-29 Takeda Chem Ind Ltd 吸収性が改善された医薬組成物
JP2003034632A (ja) * 2001-05-16 2003-02-07 Otsuka Pharmaceut Co Ltd 徐放性医薬組成物
JP2003073274A (ja) * 2001-06-20 2003-03-12 Dainippon Ink & Chem Inc キノリノン誘導体医薬組成物及びその製造方法
WO2003026619A1 (fr) * 2001-09-26 2003-04-03 Kyowa Hakko Kogyo Co., Ltd. Granules presentant des proprietes de dosage ameliorees

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JPH0717866A (ja) * 1993-06-16 1995-01-20 Meiji Seika Kaisha Ltd 医薬組成物
JP3596742B2 (ja) * 1998-07-31 2004-12-02 日研化学株式会社 陽イオン交換樹脂製剤
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06157312A (ja) * 1992-11-12 1994-06-03 Shionogi & Co Ltd 苦味改善テルフェナジンドライシロップ顆粒剤
JP2001163769A (ja) * 1999-03-25 2001-06-19 Otsuka Pharmaceut Co Ltd シロスタゾール製剤
WO2001076607A1 (fr) * 2000-04-12 2001-10-18 Nichiiko Pharmaceutical Co., Ltd. Sirop sous forme de substance seche renfermant des microcapsules de theophylline a liberation prolongee
WO2002043704A1 (fr) * 2000-12-01 2002-06-06 Kyowa Hakko Kogyo Co., Ltd. Composition a solubilite ou absorbabilite orale amelioree
JP2003026676A (ja) * 2000-12-11 2003-01-29 Takeda Chem Ind Ltd 吸収性が改善された医薬組成物
JP2003034632A (ja) * 2001-05-16 2003-02-07 Otsuka Pharmaceut Co Ltd 徐放性医薬組成物
JP2003073274A (ja) * 2001-06-20 2003-03-12 Dainippon Ink & Chem Inc キノリノン誘導体医薬組成物及びその製造方法
WO2003026619A1 (fr) * 2001-09-26 2003-04-03 Kyowa Hakko Kogyo Co., Ltd. Granules presentant des proprietes de dosage ameliorees

Cited By (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005162696A (ja) * 2003-12-04 2005-06-23 Nichiko Pharmaceutical Co Ltd 溶出性に優れたセフジトレンピボキシル製剤
JP2007269783A (ja) * 2006-03-06 2007-10-18 Toyama Chem Co Ltd トシル酸トスフロキサシンを含有する粒状固形製剤
EP2232996A2 (fr) 2007-09-12 2010-09-29 Bayer CropScience AG Traitement après récolte
EP2233004A2 (fr) 2007-09-12 2010-09-29 Bayer CropScience AG Traitement après récolte
EP2233001A2 (fr) 2007-09-12 2010-09-29 Bayer CropScience AG Traitement après récolte
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