WO2012102362A1 - 水難溶性薬物含有医薬組成物 - Google Patents
水難溶性薬物含有医薬組成物 Download PDFInfo
- Publication number
- WO2012102362A1 WO2012102362A1 PCT/JP2012/051746 JP2012051746W WO2012102362A1 WO 2012102362 A1 WO2012102362 A1 WO 2012102362A1 JP 2012051746 W JP2012051746 W JP 2012051746W WO 2012102362 A1 WO2012102362 A1 WO 2012102362A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- pharmaceutical composition
- flavor
- poorly water
- soluble drug
- polystyrene sulfonate
- Prior art date
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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
- A61K31/74—Synthetic polymeric materials
- A61K31/795—Polymers containing sulfur
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61J—CONTAINERS SPECIALLY ADAPTED FOR MEDICAL OR PHARMACEUTICAL PURPOSES; DEVICES OR METHODS SPECIALLY ADAPTED FOR BRINGING PHARMACEUTICAL PRODUCTS INTO PARTICULAR PHYSICAL OR ADMINISTERING FORMS; DEVICES FOR ADMINISTERING FOOD OR MEDICINES ORALLY; BABY COMFORTERS; DEVICES FOR RECEIVING SPITTLE
- A61J1/00—Containers specially adapted for medical or pharmaceutical purposes
-
- 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
- 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
-
- 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
-
- 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
-
- 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
- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
-
- 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
- A61K9/10—Dispersions; Emulsions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
Definitions
- the present invention relates to a pharmaceutical composition containing a poorly water-soluble drug such as an ion exchange resin.
- ion exchange resins have been used as preventive and therapeutic agents for various diseases.
- cation exchange resins such as calcium polystyrene sulfonate and sodium polystyrene sulfonate
- anion exchange resins such as cholestyramine
- ion exchange resins typified by calcium polystyrene sulfonate and sodium polystyrene sulfonate are generally insoluble in water, and thus have a unique texture (roughness).
- Patent Document 1 a powdery preparation such as a powder or a dry syrup
- Patent Document 2 a dosage form of an internal jelly
- a package containing 5 g of polystyrene sulfonate calcium is commercially available (for example, Calimate (registered trademark) powder, Calimate (registered trademark) dry syrup 92.59%), for internal use
- a jelly agent one containing 25 g of jelly agent per potion cup (containing 5 g of polystyrene sulfonate calcium) is commercially available (for example, 25 g of Argamate (registered trademark) 20% jelly).
- the above powder is orally administered in 15 to 30 g (15 to 30 g as calcium polystyrene sulfonate) a day, divided into 2 to 3 times, and the single dose is suspended in 30 to 50 mL of water.
- Daily doses of 16.2 to 32.4 g (15 to 30 g as calcium polystyrene sulfonate) are divided into 2 to 3 doses, and each dose is suspended in 30 to 50 mL of water and administered orally.
- compositions containing sodium polystyrene sulfonate, powders and dry syrup dosage forms are known, including 5 g powdered polystyrene sulfonate sodium and 3.27 g dry syrup.
- powdered polystyrene sulfonate sodium are commercially available (e.g., Keixalate (R) powder, Keixalate (R) dry syrup 76%).
- the above powder is orally administered with 30 g per day (30 g as polystyrene sulfonate) divided into 2 to 3 times, and the dose is suspended orally in 50 to 150 mL of water, and the dry syrup is 32.94 g per day.
- (30 g of polystyrene sulfonate sodium) is divided into 2 to 3 times, and the single dose is suspended orally in 50 to 150 mL of water.
- cholestyramine-containing powder is commercially available (for example, 44% Questlan (registered trademark) powder). This powder is usually taken at a dose of 9 g (4 g as cholestyramine anhydride) at a time in about 100 mL of water and taken 2 to 3 times a day.
- the subject of this invention is providing the pharmaceutical composition containing the poorly water-soluble drug with which the medication compliance was improved.
- the inventors have included a cellulose derivative in a pharmaceutical composition containing a poorly water-soluble drug, thereby reducing the rough feeling caused by the poorly water-soluble drug and having a soft mouthfeel. It was found that the suspension / dispersion stability was improved.
- the present invention provides a pharmaceutical composition containing a poorly water-soluble drug and a cellulose derivative.
- the pharmaceutical composition of the present invention has less roughness due to poorly water-soluble drugs, has a soft mouthfeel, and has excellent suspension / dispersion stability.
- the pharmaceutical composition of the present invention is characterized by containing a poorly water-soluble drug and a cellulose derivative.
- a poorly water-soluble drug used in the present invention will be described.
- a poorly water-soluble drug refers to a drug with low solubility in water.
- “solubility” defined in the 15th revised Japanese Pharmacopoeia general rules is “almost insoluble” or “extremely insoluble”.
- the drug to be used is a powder in the case where the drug is solid, and then put into water and shaken vigorously at 20 ⁇ 5 ° C. every 5 minutes for 30 seconds. The amount of water required to dissolve is 1000 mL or more.
- Examples of such poorly water-soluble drugs include, in addition to ion exchange resins, azithromycin hydrate, astazolamide, acetyl spiramycin, acetohexamide, acemetacin, azelnidipine, atorvastatin calcium hydrate, anastrozole, amiodarone hydrochloride, Amilinone, amphotericin B, amoxapine, allylestrenol, alfacalcidol, alprazolam, albendazole, aluminoprofen, allopurinol, ampiroxicam, amprenavir, amlexanox, ibudilast, imidafenacin, indapamide, urapidil, exemestane, estazotretoeth , Etizolam, enoxacin, ebastine, efavirenz, eplerenone, everolimus, efonidipine hydrochloride , Erlotinib hydroch
- ion exchange resins are preferable.
- the ion exchange resin include an anion exchange resin and a cation exchange resin.
- the anion exchange resin include colestimide, cholestyramine, sevelamer hydrochloride, and the like.
- the cation exchange resin include polystyrene sulfonates such as potassium polystyrene sulfonate and sodium polystyrene sulfonate; polycarbophil calcium and the like.
- polystyrene sulfonate polystyrene sulfonate, cholestyramine, and sevelamer hydrochloride are preferable, and polystyrene sulfonate is particularly preferable from the viewpoint of the dose per dose.
- the particle size of the poorly water-soluble drug is not particularly limited, but by reducing the particle size, the rough feeling caused by the poorly water-soluble drug can be further reduced.
- the particle size is preferably about 5 to 100 ⁇ m.
- the content of the poorly water-soluble drug may be determined by appropriately examining according to the daily dose and the content in the packaged product (dosage unit). Such a content is such that the dose per administration is, for example, about 0.05 to 50 g (preferably 0.1 to 30 g) as a free form of a poorly water-soluble drug. Specifically, when colestimide is used as the poorly water-soluble drug, the dose per dose is about 1.5 g as colestimide. When cholestyramine is used, the dose per dose is about 4 g as cholestyramine anhydride. When Sevelamer hydrochloride is used, the dose per dose is about 1 to 3 g as Sevelemer hydrochloride.
- the dosage per time will be about 5 g as a polystyrene sulfonate.
- the dose per dose is about 0.5 to 1 g as polycarbofilm calcium.
- the preferable content of the poorly water-soluble drug is 1 to 60% by mass, more preferably 5 to 40% by mass, and particularly preferably 8 to 30% by mass with respect to the whole pharmaceutical composition.
- the cellulose derivative examples include carmellose sodium, hydroxypropylmethylcellulose (hypromellose), hydroxypropylcellulose, methylcellulose, croscarmellose sodium, and the like. These can be used alone or in combination of two or more. Among these, hydroxypropyl methylcellulose, hydroxypropylcellulose, and methylcellulose are preferable, and hydroxypropylcellulose and methylcellulose are particularly preferable in terms of reduction of roughness in the oral cavity, softness, and suspension / dispersion stability. Further, the content of the cellulose derivative may be determined by appropriate examination according to the content of the poorly water-soluble drug in the pharmaceutical composition, etc., but it is reduced in roughness, softness, and suspension / dispersion stability. Therefore, the amount is preferably about 0.005 to 15% by mass, more preferably 0.01 to 5% by mass, and particularly preferably 0.05 to 2% by mass with respect to the entire pharmaceutical composition.
- composition of the present invention those containing natural polysaccharides or gelatin in addition to the poorly water-soluble drug and cellulose derivative are preferred.
- Naturally-occurring polysaccharides are not particularly limited.
- gum arabic sodium alginate, pregelatinized starch, curdlan, carrageenan ( ⁇ -carrageenan, ⁇ -carrageenan, ⁇ -carrageenan), agar, xanthan gum, guar gum, glucomannan, psyllium Seed gum, gellan gum, tamarind seed gum, tara gum, starch, locust bean gum, pectin and the like.
- carrageenan ⁇ -carrageenan, ⁇ -carrageenan, ⁇ -carrageenan
- agar xanthan gum
- guar gum glucomannan
- psyllium Seed gum gellan gum
- tamarind seed gum tara gum
- starch locust bean gum
- pectin and the like may be used alone or in combination of two or more.
- one or more selected from carrageenan, xanthan gum, locust bean gum, guar gum, and agar are preferable.
- locust bean gum in addition to carrageenan, the elasticity of the pharmaceutical composition can be increased, and by using agar, the hardness of the pharmaceutical composition can be increased.
- one or more selected from carrageenan, xanthan gum, and locust bean gum are more preferable, and a combination of xanthan gum and locust bean gum is particularly preferable.
- the content of the naturally-derived polysaccharide may be determined by appropriate examination according to the content of the poorly water-soluble drug in the pharmaceutical composition, etc., but from the viewpoint of softening and softness of the roughness, On the other hand, it is preferably about 0.01 to 15% by mass, more preferably 0.05 to 5% by mass, and particularly preferably 0.1 to 2% by mass.
- the pharmaceutical composition of the present invention may contain formulation additives such as pH adjusters, sweeteners, flavors, preservatives, etc. in addition to the aforementioned poorly water-soluble drugs, cellulose derivatives and naturally occurring polysaccharides. These may be used alone or in combination of two or more.
- Examples of the pH regulator include ascorbic acid, magnesium L-aspartate, benzoic acid, sodium benzoate, sodium chloride, dilute hydrochloric acid, calcium citrate, citric acid hydrate, sodium citrate hydrate, dicitrate dicitrate.
- sweetener examples include aspartame, liquid sugar, fructose, fructose glucose liquid sugar, reduced maltose water candy, high glucose water candy, saccharin, saccharin sodium hydrate, sucralose, purified white sugar, purified honey, sorbitol, sorbitol solution, Simple syrup, white sugar, honey, glucose fructose liquid sugar, powdered reduced maltose water candy, maltitol, maltitol liquid, water candy and the like.
- saccharin, saccharin sodium hydrate, sucralose, maltitol, maltitol solution, reduced maltose water candy, powdered reduced maltose water candy and the like are preferable.
- the flavor examples include orange flavor, kiwi fruit flavor, grapefruit flavor, strawberry flavor, cherry flavor, fruit flavor, muscat flavor, raspberry flavor, apple flavor, lemon flavor, caramel flavor, green tea flavor, cocoa flavor, and coffee flavor.
- Kiwifruit flavor, strawberry flavor, raspberry flavor and the like are preferable from the viewpoint that when the pharmaceutical composition of the present invention is taken, the reduced roughness is felt as a fruit seed.
- the above-described flavor may be stored separately from the pharmaceutical composition during packaging. In this case, it is good also as a kit which combined the pharmaceutical formulation and flavor which stored the pharmaceutical composition of this invention in stick packaging.
- preservative examples include benzoic acid, sodium benzoate, butyl paraoxybenzoate, and propyl paraoxybenzoate.
- a suspension is preferred. Thereby, even when it contains a poorly water-soluble drug (polystyrene sulfonate, cholestyramine, etc.) with a large dose per dose, it can be taken easily.
- the suspending agent as described above include those that require suspension during use and those that do not require suspension during use. From the viewpoint of medication compliance, those that do not require suspension during use are preferable.
- the appearance of the suspending agent that does not require suspension during use include gummy-like, cream-like, jelly-like, bavaria-like, pudding-like, and paste-like. These appearances can be roughly classified according to their viscosity, viscoelasticity and gel strength.
- suspending agents as described above, jelly-like ones are preferable.
- it can be taken without using a spoon or the like for preparation, resuspension operation, or taking the medicine, so that the usual single dose is packaged (packaged product) ) Is less complicated.
- it since it is suitable for packaging such as tubes and sticks described later, it is excellent in portability and compliance is improved.
- the pharmaceutical composition of the present invention can be produced and formulated according to known methods described in the 15th revised Japanese Pharmacopoeia, General Rules for Preparations, etc., and these descriptions.
- a package that can prevent liquid or solid foreign matter from entering under normal handling or storage conditions is preferable, and a package that can be stored airtight is more preferable.
- the package can be either regular or irregular.
- Such packaging is not particularly limited, but tubes, SP (Stripe Package) packaging, and stick packaging are preferable.
- SP Stripe Package
- stick packaging are preferable.
- one or more known packaging materials such as metal foil such as aluminum foil and polyethylene are used. What is necessary is just to manufacture by a well-known method using a sheet
- the method for forming a sheet into a multilayer structure using the two or more types of packaging materials include a method for producing a laminated sheet by laminating the packaging materials.
- the laminated sheet can be produced by a known method such as extrusion lamination, dry lamination, coextrusion lamination, thermal lamination, wet lamination, non-solvent lamination, heat lamination and the like.
- a commercial item can also be used for the sheet
- a pharmaceutical preparation in which the pharmaceutical composition of the present invention is packaged in a tube, SP packaging, stick packaging, or the like can be secondarily wrapped in pillow packaging, cans, bottles, bags, etc. as a small packaging unit in which a certain amount is collected. .
- Test Example 1 Preparation and evaluation of jelly-like pharmaceutical composition (oral solution) (1) Each component described in Table 1 was mixed, and this was heated and cooled to prepare a jelly-like pharmaceutical composition.
- the jelly-like pharmaceutical compositions of Examples 1 to 4 and Comparative Example 1 were adjusted to a pH of about 5 using sorbic acid and sodium citrate hydrate.
- the pharmaceutical compositions of Comparative Examples 1 to 6 were so soft that they did not require chewing and had little roughness, but were insufficient in terms of suspension and dispersion stability.
- the pharmaceutical compositions of Examples 1 to 4 were soft enough not to chew, had little roughness, and had excellent suspension / dispersion stability. From these results, it was found that the suspension / dispersion stability can be improved by blending the cellulose derivative while maintaining a low roughness and a soft mouthfeel.
- Example 5 Jelly-like pharmaceutical composition (internal solution) Cholestyramine anhydride 8g, xanthan gum 0.24g, locust bean gum 0.44g, methylcellulose 0.6g, powdered reduced maltose water candy 12g, sucralose trace amount dissolved and dispersed in water, then heated and cooled to a total amount of 100g A jelly-like pharmaceutical composition was prepared. Next, 50 g of each of the obtained jelly-like pharmaceutical compositions was stick-wrapped using an aluminum / polyethylene laminate film.
- Example 6 Jelly-like pharmaceutical composition (internal solution) Sevelamer hydrochloride 9g, xanthan gum 0.24g, locust bean gum 0.44g, methylcellulose 0.2g, powdered reduced maltose water candy 7.2g, sorbic acid 0.45g, sodium citrate hydrate 0.54g, sucralose trace amount It was dissolved and dispersed in water, and then heated and cooled to prepare a total amount of 90 g of a jelly-like pharmaceutical composition. Next, 10 g of each jelly-like pharmaceutical composition obtained was stick-packaged using an aluminum / polyethylene laminate film.
- the pharmaceutical composition of the present invention Even if the pharmaceutical composition of the present invention is stored for a long period of time, a poorly water-soluble drug such as an ion exchange resin in the preparation stably maintains a suspended / dispersed state. Further, there is no need to adopt a packaging form that is bulky when packaged (packed) after being divided into ordinary single doses, and is excellent in portability. Therefore, since the pharmaceutical composition of the present invention does not require preparation at the time of use or a tool such as a spoon when taking a poorly water-soluble drug, it can be used for taking a usual single dose (packaged product). There is no complication, and it is excellent in the portability of the packaged product along with the packaging, satisfying the medication compliance, and useful.
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Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020137019475A KR101947198B1 (ko) | 2011-01-27 | 2012-01-27 | 수난용성 약물 함유 의약 조성물 |
CN2012800068111A CN103338789A (zh) | 2011-01-27 | 2012-01-27 | 含有水难溶性药物的医药组合物 |
RU2013139558A RU2678587C2 (ru) | 2011-01-27 | 2012-01-27 | Фармацевтическая композиция, содержащая лекарственное средство, имеющее слабую растворимость в воде |
JP2012554854A JP5906195B2 (ja) | 2011-01-27 | 2012-01-27 | 水難溶性薬物含有医薬組成物 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2011015296 | 2011-01-27 | ||
JP2011-015296 | 2011-01-27 |
Publications (1)
Publication Number | Publication Date |
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WO2012102362A1 true WO2012102362A1 (ja) | 2012-08-02 |
Family
ID=46580925
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/JP2012/051746 WO2012102362A1 (ja) | 2011-01-27 | 2012-01-27 | 水難溶性薬物含有医薬組成物 |
Country Status (6)
Country | Link |
---|---|
JP (1) | JP5906195B2 (zh) |
KR (1) | KR101947198B1 (zh) |
CN (2) | CN103338789A (zh) |
RU (1) | RU2678587C2 (zh) |
TW (1) | TWI605837B (zh) |
WO (1) | WO2012102362A1 (zh) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104644556A (zh) * | 2013-11-22 | 2015-05-27 | 沈阳药科大学 | 盐酸依福地平固体粉末及其制备方法 |
WO2016023822A1 (en) * | 2014-08-15 | 2016-02-18 | Boehringer Ingelheim International Gmbh | Afatinib pharmaceutical kit for cancer treatment |
US9433640B2 (en) | 2014-12-23 | 2016-09-06 | Ardelyx, Inc. | Compositions and methods for treating hyperkalemia |
WO2017061562A1 (ja) * | 2015-10-07 | 2017-04-13 | 塩水港精糖株式会社 | タキサン化合物を内包するリポソーム |
US9655921B2 (en) | 2014-12-23 | 2017-05-23 | Ardelyx, Inc. | Compositions and methods for treating hyperkalemia |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112294755A (zh) * | 2020-11-18 | 2021-02-02 | 吉林大学 | 含有水难溶性药物的医药组合物 |
IT202200006605A1 (it) | 2022-04-04 | 2023-10-04 | Golden Pharma S R L | Stick pack per la conservazione separata dei principi attivi dei medicinali, integratori alimentari, dispositivi medici |
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US6180587B1 (en) * | 1999-09-28 | 2001-01-30 | Colgate Palmolive Company | Multiple phase compositions |
CN101632651B (zh) * | 2009-08-31 | 2010-12-08 | 河北科技大学 | 一种利培酮的口腔速溶膜及其制备方法 |
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2012
- 2012-01-20 TW TW101102465A patent/TWI605837B/zh not_active IP Right Cessation
- 2012-01-27 CN CN2012800068111A patent/CN103338789A/zh active Pending
- 2012-01-27 KR KR1020137019475A patent/KR101947198B1/ko active IP Right Grant
- 2012-01-27 WO PCT/JP2012/051746 patent/WO2012102362A1/ja active Application Filing
- 2012-01-27 CN CN201810586603.2A patent/CN108524445A/zh active Pending
- 2012-01-27 JP JP2012554854A patent/JP5906195B2/ja active Active
- 2012-01-27 RU RU2013139558A patent/RU2678587C2/ru active
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JPH01172324A (ja) * | 1987-12-15 | 1989-07-07 | Armour Internatl Co | コレスチラミン組成物及びその製造法 |
WO1999020285A1 (fr) * | 1997-10-16 | 1999-04-29 | Sanwa Kagaku Kenkyusho Co., Ltd. | Preparations de gels contenant un polystyrenesulfonate |
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Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104644556A (zh) * | 2013-11-22 | 2015-05-27 | 沈阳药科大学 | 盐酸依福地平固体粉末及其制备方法 |
WO2016023822A1 (en) * | 2014-08-15 | 2016-02-18 | Boehringer Ingelheim International Gmbh | Afatinib pharmaceutical kit for cancer treatment |
US9433640B2 (en) | 2014-12-23 | 2016-09-06 | Ardelyx, Inc. | Compositions and methods for treating hyperkalemia |
US9545425B2 (en) * | 2014-12-23 | 2017-01-17 | Ardelyx, Inc. | Pharmaceutical compositions for treating hyperkalemia |
US9549947B2 (en) * | 2014-12-23 | 2017-01-24 | Ardelyx, Inc. | Pharmaceutical compositions for treating hyperkalemia |
US9655921B2 (en) | 2014-12-23 | 2017-05-23 | Ardelyx, Inc. | Compositions and methods for treating hyperkalemia |
US9867848B2 (en) | 2014-12-23 | 2018-01-16 | Ardelyx, Inc. | Compositions and methods for treating hyperkalemia |
US9919006B2 (en) | 2014-12-23 | 2018-03-20 | Ardelyx, Inc. | Compositions and methods for treating hyperkalemia |
WO2017061562A1 (ja) * | 2015-10-07 | 2017-04-13 | 塩水港精糖株式会社 | タキサン化合物を内包するリポソーム |
JPWO2017061562A1 (ja) * | 2015-10-07 | 2018-07-05 | 塩水港精糖株式会社 | タキサン化合物を内包するリポソーム |
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JPWO2012102362A1 (ja) | 2014-06-30 |
CN103338789A (zh) | 2013-10-02 |
KR20140005930A (ko) | 2014-01-15 |
CN108524445A (zh) | 2018-09-14 |
KR101947198B1 (ko) | 2019-02-12 |
TW201309344A (zh) | 2013-03-01 |
RU2013139558A (ru) | 2015-03-10 |
RU2678587C2 (ru) | 2019-01-30 |
JP5906195B2 (ja) | 2016-04-20 |
TWI605837B (zh) | 2017-11-21 |
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