WO2013129545A1 - Préparation solide contenant du loxoprofène pour utilisation externe - Google Patents

Préparation solide contenant du loxoprofène pour utilisation externe Download PDF

Info

Publication number
WO2013129545A1
WO2013129545A1 PCT/JP2013/055314 JP2013055314W WO2013129545A1 WO 2013129545 A1 WO2013129545 A1 WO 2013129545A1 JP 2013055314 W JP2013055314 W JP 2013055314W WO 2013129545 A1 WO2013129545 A1 WO 2013129545A1
Authority
WO
WIPO (PCT)
Prior art keywords
oil
solid preparation
loxoprofen
external
salt
Prior art date
Application number
PCT/JP2013/055314
Other languages
English (en)
Japanese (ja)
Inventor
裕明 小林
Original Assignee
興和株式会社
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 興和株式会社 filed Critical 興和株式会社
Priority to JP2014502351A priority Critical patent/JP6224578B2/ja
Publication of WO2013129545A1 publication Critical patent/WO2013129545A1/fr

Links

Classifications

    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid 
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12—Carboxylic acids; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Definitions

  • the present invention relates to an external solid preparation containing loxoprofen or a salt thereof, a shape retention agent for the external solid preparation, and a hardness enhancer.
  • an external preparation for skin As a preparation to be applied to the skin, an external preparation for skin is known, which is roughly classified into an application agent and a patch.
  • the coating agent include an external solid agent (tick agent), an external liquid agent (liniment agent, lotion agent), an ointment, a cream agent, and a gel agent.
  • the external solid agent is stored in an appropriate container.
  • the drug can be applied to the skin without staining hands and fingers, it is difficult to cause discomfort during use.
  • Patent Documents 1 to 6 there are many problems with the hardness and shape retention of the preparation, and various studies have been made so far. None of the preparations were satisfactory in terms of hardness and shape retention.
  • loxoprofen is a kind of phenylpropionic acid-based non-steroidal anti-inflammatory analgesic (NSAID).
  • NSAID non-steroidal anti-inflammatory analgesic
  • This medicine contains loxoprofen sodium hydrate, and it is used to treat osteoarthritis, myalgia and swelling / pain after trauma, as well as antiphlogistic / analgesic, poultice, tape, gel
  • the agents are known (Patent Documents 7 to 9 and Non-Patent Document 1), no external solid preparation containing loxoprofen has been known yet.
  • An object of the present invention is to provide an external solid preparation, a shape retention agent for an external solid preparation, and a hardness enhancer that are excellent in shape retention and have an appropriate hardness.
  • this invention provides the external solid agent containing the following components (A), (B), and (C).
  • (C) Terpenes Moreover, this invention provides the shape retention agent of the external solid agent containing terpenes.
  • the present invention provides a hardness enhancer capable of adjusting the hardness of an external solid preparation containing loxoprofen or a salt thereof.
  • the external solid preparation of the present invention is excellent in shape retention and has an appropriate hardness that is easy to apply, the commercial value is high.
  • the shape retention agent of this invention is excellent in the shape retention ability of the external solid agent.
  • the hardness enhancer of this invention is excellent in the hardness adjustment capability of the solid agent for external use.
  • the loxoprofen or a salt thereof contained in the external solid preparation of the present invention includes loxoprofen itself, a pharmaceutically acceptable salt of loxoprofen, and a solvate of these with water, alcohol and the like.
  • loxoprofen sodium hydrate (chemical name: Monosodium 2- [4-[(2-oxocyclopentyl) methyl] phenyl] propanoate dihydrate) is preferable.
  • Loxoprofen or a salt thereof is a known compound, and can be produced by a known method, or a commercially available product can be used.
  • the content of loxoprofen or a salt thereof may be appropriately determined according to the desired anti-inflammatory analgesic effect, but from the viewpoint of imparting appropriate hardness to the external solid preparation, In 100 parts by mass of the agent, 0.01 to 15 parts by mass is preferable, 0.01 to 10 parts by mass is more preferable, 0.1 to 5 parts by mass is further preferable, and 0.5 to 3 parts by mass is particularly preferable.
  • the saturated higher fatty acid salt contained in the external preparation for external use of the present invention functions as a soap gel base.
  • Saturated higher fatty acid salts are preferably those having 12 to 22 carbon atoms. Examples include laurate, myristate, pentadecanoate, palmitate, margarate, stearate, isostearate, arachidate, behenate, etc., and these may be used alone Two or more kinds may be used in combination. Among these, those having 14 to 22 carbon atoms are more preferable. Specifically, palmitate, myristate, stearate and isostearate are preferable, and stearate and isostearate are mentioned.
  • inorganic salts such as aluminum salt, potassium salt, sodium salt, magnesium salt, are preferable, and sodium salt is especially preferable.
  • the saturated higher fatty acid salt include sodium myristate, potassium myristate, sodium palmitate, aluminum stearate, potassium stearate, sodium stearate, magnesium stearate, sodium isostearate and the like. More preferred is sodium stearate.
  • a saturated higher fatty acid salt is formed by blending a saturated higher fatty acid and a compound that forms a salt with the saturated higher fatty acid (potassium hydroxide, sodium hydroxide, etc.). You may let them.
  • a soap base or a medicinal soap containing a saturated higher fatty acid salt (such as a sodium salt of a saturated higher fatty acid) may also be used.
  • the content of the saturated higher fatty acid salt is preferably 0.1 to 30 parts by mass, more preferably 0.5 to 20 parts by mass, further preferably 1 to 15 parts by mass, in 100 parts by mass of the external solid preparation. 5 to 10 parts by mass is particularly preferable.
  • (A) Loxoprofen or a salt thereof (in terms of loxoprofen sodium anhydrate) and (B) a mass ratio of content of saturated higher fatty acid salt [(B) / (A)] gives moderate hardness. In view of the above, 1 to 25 is preferable, 3 to 15 is more preferable, and 5 to 10 is still more preferable.
  • the terpenes contained in the external solid preparation of the present invention are not particularly limited, and examples thereof include monoterpenes and sesquiterpenes.
  • Examples of such terpenes include, for example, isoborneol, iron, osimene, carveol, carbotanaseton, carbomenton, carvone, caren, caron, camphene, camphor, geraniol, sabinene, safranal, cyclocitral, citral, citronellal, citronellic acid, Citronellol, Cineol, Cymen, Silvestrene, Isotujol, Tujon, Terpineol, Terpinene, Terpinolene, Tricyclene, Nerol, Pinene, Pinoccamphorol, Pinol, Piperithenone, Ferrandral, Ferrandrene, Fentchen, Fentyl alcohol, Perillyl alcohol , Perylaldehy
  • camphor geraniol, citronellal, terpineol, borneol, menthol, limonene and the like are preferable, camphor and menthol are more preferable, and dl-camphor, l-menthol and dl-menthol are particularly preferable.
  • an essential oil containing the terpenes as described above may be used.
  • Such essential oils include, for example, anise oil, ylang ylang oil, iris oil, fennel oil, orange oil, cananga oil, chamomile oil, kayap oil, caraway oil, kubeb oil, grapefruit oil, cinnamon oil, coriander oil, saffron oil Oil, salamander oil, perilla oil, citriodora oil, citronella oil, ginger oil, gingergrass oil, gingergrass oil, spearmint oil, peppermint oil, geranium oil, geranium oil, clove oil, turpentine oil, spruce oil , Neroli oil, basil oil, peppermint oil, palmarosa oil, pimento oil, petitgren oil, bay oil, peniroyal oil, henoposi oil, bergamot oil, bored rose oil, pepper oil, marjolan oil,
  • the content of the terpenes may be appropriately determined according to the desired hardness and the local stimulating action based on the analgesic and analgesic action in the external solid preparation, but from the viewpoint of shape retention, 0.01 to 15 parts by mass is preferable, 0.1 to 10 parts by mass is more preferable, and 0.5 to 7 parts by mass is even more preferable.
  • the mass ratio [(C) / (A)] of (A) loxoprofen or a salt thereof (in terms of loxoprofen sodium anhydrate) and (C) terpenes is 0 from the viewpoint of shape retention. 0.01 to 15 is preferable, 0.1 to 10 is more preferable, and 0.5 to 7 is still more preferable.
  • the external solid agent of the present invention preferably contains component (D) and other alcohols.
  • Other alcohols may be used as long as they function as a base for external solid preparations, and examples thereof include monohydric alcohols and polyhydric alcohols. May be. However, terpenes having an alcoholic hydroxyl group are excluded from other alcohols.
  • Examples of the monohydric alcohol include methanol, ethanol, geraniol-modified alcohol, methanol-modified alcohol, propanol, isopropanol, butanol, isobutanol, octaacetyl sucrose-modified alcohol, phenylethyl alcohol, phenylethyl alcohol-modified alcohol, and the like.
  • ethanol, geraniol-modified alcohol, methanol-modified alcohol, isopropanol, octaacetyl sucrose-modified alcohol, phenylethyl alcohol, phenylethyl alcohol-modified alcohol and the like are preferable.
  • the polyhydric alcohol means one having a plurality of alcoholic hydroxyl groups.
  • dihydric alcohols such as ethylene glycol, propylene glycol, 1,3-butylene glycol, polyethylene glycol, polypropylene glycol, polyoxyethylene polyoxypropylene glycol; trihydric alcohols such as glycerin and concentrated glycerin; erythritol, sorbitol, mannitol, etc. Sugar alcohol and the like.
  • propylene glycol, 1,3-butylene glycol, polyethylene glycol, glycerin and concentrated glycerin are preferable.
  • the content of other alcohols is usually 10 to 90 parts by weight, preferably 15 to 85 parts by weight, and more preferably 20 to 80 parts by weight in 100 parts by weight of the external solid agent.
  • the content of the monohydric alcohol is preferably 5 to 70 parts by mass, more preferably 7 to 60 parts by mass, and further preferably 10 to 50 parts by mass in 100 parts by mass of the external solid agent.
  • the content of the polyhydric alcohol is preferably 5 to 80 parts by mass, more preferably 10 to 70 parts by mass, and further preferably 20 to 60 parts by mass in 100 parts by mass of the external solid agent.
  • the solid preparation for external use of the present invention can be prepared by adding components (A) to (C) to the above-mentioned other alcohols (component (D) as necessary. ) And other preparation additives, dissolved or dispersed, and then solidified.
  • other preparation additives include oils such as diisopropyl adipate, crotamiton, squalane, squalene, diethyl sebacate, castor oil, isopropyl palmitate, isopropyl myristate, cetyl myristate, myristyl myristate; sucrose fatty acid ester , Surfactants such as sorbitan fatty acid ester, polyoxyethylene hydrogenated castor oil, polyoxyethylene sorbitan fatty acid ester, polyglycerin fatty acid ester, sodium lauryl sulfate, lauromacrogol, polyoxyethylene cetyl ether; oleyl alcohol, lauryl alcohol, etc.
  • the said antioxidant is mentioned as a formulation additive which enhances the skin permeability of loxoprofen.
  • examples of the antioxidant include sodium nitrite, ascorbic acid, L-ascorbic acid stearate, sodium hydrogen sulfite, alpha thioglycerin, sodium edetate, erythorbic acid, cysteine hydrochloride, dried sodium sulfite, and citric acid hydrate.
  • an antioxidant When an antioxidant is added to the external solid preparation of the present invention, its content may be appropriately determined according to the type of the antioxidant, etc., but 0.01 to 50 mass in 100 mass parts of the external solid preparation. Part, preferably 0.02 to 10 parts by weight, more preferably 0.03 to 2 parts by weight.
  • malic acid and / or citric acid hydrate When malic acid and / or citric acid hydrate is used as an antioxidant, it is used in combination with higher fatty acids such as myristic acid, palmitic acid, stearic acid and isostearic acid from the viewpoint of enhancing the skin permeability of loxoprofen. It is preferable to do this.
  • the content of malic acid and / or citric acid hydrate is preferably 0.1 to 3 parts by mass in 100 parts by mass of the solid preparation for external use, while the content of higher fatty acid is 0.1 ⁇ 5 parts by mass are preferred.
  • the terpene has a hydroxyl group
  • metal carbonates such as urea, calcium carbonate and magnesium carbonate, sodium bisulfite, 2-mercaptobenzimidazole, etc. It is preferable to further contain.
  • the content of these components in this case may be appropriately examined, but it is preferable to contain 0.5 to 3 parts by mass of urea in 100 parts by mass of the external solid preparation.
  • the metal carbonate is preferably contained in an amount of 0.01 to 3 parts by mass
  • the sodium hydrogen sulfite is preferably contained in an amount of 0.01 to 2 parts by mass
  • the 2-mercaptobenzimidazole is contained in an amount of 0.01 to 2 parts by mass.
  • the metal carbonate is preferably contained in an amount of 0.01 to 3 parts by mass
  • the sodium hydrogen sulfite is preferably contained in an amount of 0.01 to 2 parts by mass
  • the 2-mercaptobenzimidazole is contained in an amount of 0.01 to 2 parts by mass.
  • the solid preparation for external use of the present invention includes loxoprofen or a salt thereof, a drug other than terpenes, for example, a local stimulating component, an analgesic component, an anti-inflammatory component, a bactericidal / disinfecting component, an astringent / protective component, a blood circulation promoting component, A histamine component, crude drugs, etc. are mentioned, These may contain 1 type, or 2 or more types.
  • Examples of the local stimulation component include capsaicin, nonanoic acid vanillylamide, and the like.
  • Examples of the analgesic component include salicylic acid, glycol salicylate, and methyl salicylate.
  • Examples of the anti-inflammatory component include glycyrrhizic acid, glycyrrhetinic acid, dipotassium glycyrrhizinate and the like.
  • Examples of the sterilizing / disinfecting component include thymol.
  • Examples of the astringent / protective component include zinc oxide.
  • Examples of the blood circulation promoting component include benzyl nicotinate, heparin-like substances, sodium polyethylene sulfonate, and the like.
  • antihistamine component examples include azelastine hydrochloride, alimemazine tartrate, istipendil hydrochloride, iproheptin hydrochloride, epinastine hydrochloride, emedastine fumarate, carbinoxamine diphenyldisulfonate, carbinoxamine maleate, Clemastine fumarate, dl-chlorpheniramine maleate, d-chlorpheniramine maleate, ketotifen fumarate, difeterol hydrochloride, difeterol phosphate, diphenylpyraline hydrochloride, diphenylpyraline theocrate , Diphenhydramine hydrochloride, diphenhydramine salicylate, diphenhydramine tannate, triprolidine hydrochloride, tripelenamine hydrochloride, tondilamine hydrochloride, phenetazine hydrochloride, promethazine hydrochloride, mequita
  • Herbal medicines include, for example, arnica, goldfish, jaundice, yellow lantern, dry cocoon, cinnamon bark, safflower, yam, horse chestnut, cocoon, wood tempura, salmon plum, and extracts thereof (extracts, tinctures, etc.). Can be mentioned.
  • the solid preparation for external use of the present invention is stored in a container, and it is preferable to use a sealed container as the container.
  • a sealed container an extrusion type or dial type lifting and lowering type container is preferable from the viewpoint of use and storage of the external solid agent.
  • the external solid preparation of the present invention is excellent in shape retention and has an appropriate hardness that is easy to apply, and therefore has a high commercial value.
  • loxoprofen or a salt thereof exhibits an anti-inflammatory analgesic effect as a phenylpropionic acid-based non-steroidal anti-inflammatory analgesic agent, and terpenes exhibit an analgesic and analgesic effect due to local stimulating action. It is extremely useful as a transdermal absorption-type analgesic / anti-inflammatory agent.
  • Applicable symptoms and diseases include osteoarthritis, shoulder periarthritis, tendon / tendonitis, peritonitis, humerus condyleitis, muscle pain, swelling / pain after trauma, shoulder stiffness, shoulder stiffness Pain, low back pain, joint pain, tendonitis, elbow pain, bruise, sprain, fracture pain, muscle fatigue and the like.
  • the shape retention agent of this invention is excellent in the shape retention ability of the external solid agent.
  • the hardness enhancer of this invention is excellent in the hardness adjustment capability of the solid agent for external use.
  • Test example 1 Briton-Robinson broad-area buffer (pH 7) and absolute ethanol were mixed at a ratio of 1: 1 to prepare a mixed solution.
  • Loxoprofen sodium hydrate, l-menthol and sodium stearate were added to the concentrations shown in Table 1 above. It was made to melt
  • the “skin” was evaluated by the presence or absence of a gap between the external solid agent and the inner wall of the glass bottle. The results are shown in Table 1.
  • a solid preparation for external use (Reference Example 1) containing a saturated higher fatty acid salt as a base and containing sodium loxoprofen hydrate is externally used after being stored for 1 month compared with immediately after the start of storage. A gap was generated between the solid agent and the inner wall of the glass bottle, and skin was observed. On the other hand, the solid preparation for external use (Example 1) further containing l-menthol did not show any gaps even after being stored for 1 month, and no skin was observed. From this result, although 1-menthol, which is a terpene, is a volatile component, it enhances the shape retention of external solid preparations. Terpenes are external solids containing loxoprofen or a salt thereof. It turns out that it has an effect
  • Test example 2 A mixture obtained by mixing Briton-Robinson broad-area buffer (pH 7) and absolute ethanol at a ratio of 1: 1 was prepared, and loxoprofen sodium hydrate, l-menthol and sodium stearate so as to have the concentrations shown in Table 2 was dissolved in the above mixed solution, and the pH was adjusted to 8 to obtain a liquid for external solid preparation. After filling 10 mL of the obtained external solid preparation liquid into a transparent 10K glass bottle and solidifying at room temperature, the external solid preparation was cut out (8 mm ⁇ 8 mm ⁇ 8 mm) using a rheometer (manufactured by FUDOH) to obtain hardness (g / cm 2 ) was measured and the results are shown in Table 2.
  • loxoprofen or a salt thereof has the hardness enhancing action of the external solid preparation.
  • the solid preparation for external use of Example 2 had moderate hardness, and was suitable for application
  • Example 3 Each component was heated and dissolved as necessary to achieve the concentrations shown in Table 3, filled in a container and cooled to room temperature to produce external solid preparations of Formulations 1-8.

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Dermatology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)

Abstract

La présente invention concerne : une préparation solide pour utilisation externe qui présente une excellente rétention de forme et une dureté modérée ; et un agent de rétention de forme et un agent augmentant la dureté qui sont pour utilisation dans des préparations solides pour utilisation externe. La présente invention concerne une préparation solide pour utilisation externe qui comprend (A) du loxoprofène ou un sel de celui-ci, (B) un sel d'acide gras supérieur saturé et (C) un terpène.
PCT/JP2013/055314 2012-02-29 2013-02-28 Préparation solide contenant du loxoprofène pour utilisation externe WO2013129545A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2014502351A JP6224578B2 (ja) 2012-02-29 2013-02-28 ロキソプロフェン含有外用固形剤

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2012-043976 2012-02-29
JP2012043976 2012-02-29
JP2012-043975 2012-02-29
JP2012043975 2012-02-29

Publications (1)

Publication Number Publication Date
WO2013129545A1 true WO2013129545A1 (fr) 2013-09-06

Family

ID=49082737

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2013/055314 WO2013129545A1 (fr) 2012-02-29 2013-02-28 Préparation solide contenant du loxoprofène pour utilisation externe

Country Status (2)

Country Link
JP (2) JP6224578B2 (fr)
WO (1) WO2013129545A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014166979A (ja) * 2012-06-28 2014-09-11 Kowa Company Ltd ロキソプロフェン含有外用固形剤
JP2015027971A (ja) * 2013-07-31 2015-02-12 興和株式会社 ロキソプロフェン含有外用塗布剤
JP2015071594A (ja) * 2013-09-04 2015-04-16 興和株式会社 ロキソプロフェンを含有する外用塗布剤

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6420102B2 (ja) * 2013-09-04 2018-11-07 興和株式会社 ロキソプロフェン含有外用固形剤及び該外用固形剤の保存安定化剤

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005047906A (ja) * 2003-07-16 2005-02-24 Taisho Pharmaceut Co Ltd 外用消炎鎮痛剤組成物
JP2005047907A (ja) * 2003-07-16 2005-02-24 Taisho Pharmaceut Co Ltd 外用消炎鎮痛剤組成物
JP2005047908A (ja) * 2003-07-16 2005-02-24 Taisho Pharmaceut Co Ltd 外用消炎鎮痛剤組成物

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005047906A (ja) * 2003-07-16 2005-02-24 Taisho Pharmaceut Co Ltd 外用消炎鎮痛剤組成物
JP2005047907A (ja) * 2003-07-16 2005-02-24 Taisho Pharmaceut Co Ltd 外用消炎鎮痛剤組成物
JP2005047908A (ja) * 2003-07-16 2005-02-24 Taisho Pharmaceut Co Ltd 外用消炎鎮痛剤組成物

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014166979A (ja) * 2012-06-28 2014-09-11 Kowa Company Ltd ロキソプロフェン含有外用固形剤
JP2015027971A (ja) * 2013-07-31 2015-02-12 興和株式会社 ロキソプロフェン含有外用塗布剤
JP2015071594A (ja) * 2013-09-04 2015-04-16 興和株式会社 ロキソプロフェンを含有する外用塗布剤

Also Published As

Publication number Publication date
JPWO2013129545A1 (ja) 2015-07-30
JP6224578B2 (ja) 2017-11-01
JP2017226705A (ja) 2017-12-28

Similar Documents

Publication Publication Date Title
JP6189668B2 (ja) ロキソプロフェン含有外用塗布剤
JP7367124B2 (ja) ロキソプロフェンを含有する医薬製剤（弐）
JP6397100B2 (ja) ロキソプロフェンを含有する医薬組成物３
JP2018123172A (ja) ロキソプロフェン含有外用固形剤
JP2017226705A (ja) ロキソプロフェン含有外用固形剤
JP6738120B2 (ja) 外用医薬組成物
JP2018021002A (ja) ロキソプロフェンを含有してなる医薬製剤
JP2023080151A (ja) ロキソプロフェン含有の医薬製剤（さん）
JP2020073615A (ja) ロキソプロフェンを含有する医薬製剤（に）
JP2019081755A (ja) 組成物
JP6114646B2 (ja) ロキソプロフェン含有外用固形剤
JP6420101B2 (ja) ロキソプロフェンを含有する外用塗布剤
JP6420102B2 (ja) ロキソプロフェン含有外用固形剤及び該外用固形剤の保存安定化剤
JP2018021027A (ja) ロキソプロフェンを含有する医薬製剤
JP2017155042A (ja) ロキソプロフェン含有的医薬製剤
JP2017197537A (ja) ロキソプロフェン含む医薬の製剤
JP2004210668A (ja) 医薬外用組成物
JP2018021004A (ja) ロキソプロフェンを含有してなる医薬製剤
JP2003095983A (ja) 皮膚外用剤組成物
JP2018039775A (ja) ロキソプロフェン含有医薬製剤
JP2024055826A (ja) ロキソプロフェン又はその塩、およびサリチル酸類を含有する医薬組成物
JP2024091588A (ja) ヘパリン類似物質、および、ロキソプロフェン、その塩およびそれらの水和物からなる群から選択される少なくとも一種を含有する皮膚外用剤
JP2024091587A (ja) ヘパリン類似物質を含有する皮膚外用剤
JP2020045315A (ja) ロキソプロフェンを含有する医薬製剤
JP2020094043A (ja) ロキソプロフェンを含有する組成物

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 13755771

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2014502351

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 13755771

Country of ref document: EP

Kind code of ref document: A1