WO2012018329A1 - Film-forming composition for soft capsules - Google Patents
Film-forming composition for soft capsules Download PDFInfo
- Publication number
- WO2012018329A1 WO2012018329A1 PCT/US2010/044419 US2010044419W WO2012018329A1 WO 2012018329 A1 WO2012018329 A1 WO 2012018329A1 US 2010044419 W US2010044419 W US 2010044419W WO 2012018329 A1 WO2012018329 A1 WO 2012018329A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- film
- capsule
- forming composition
- soft capsule
- Prior art date
Links
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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4816—Wall or shell material
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
- A23P20/00—Coating of foodstuffs; Coatings therefor; Making laminated, multi-layered, stuffed or hollow foodstuffs
- A23P20/10—Coating with edible coatings, e.g. with oils or fats
- A23P20/105—Coating with compositions containing vegetable or microbial fermentation gums, e.g. cellulose or derivatives; Coating with edible polymers, e.g. polyvinyalcohol
-
- 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
-
- 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
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/732—Starch; Amylose; Amylopectin; 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4866—Organic macromolecular compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2991—Coated
Definitions
- the present invention relates to a film-forming composition for soft capsules suitably used for forming soft capsules and a soft capsule prepared using the composition.
- Soft capsules have widely been employed in the fields of pharmaceutical preparations, cosmetics and foods.
- gelatin has widely been used as a principal component for constituting the shell of such a soft capsule, and gelatin is mainly produced from the bone of cattle and the skin of swine.
- a problem arises such that vegetarians, people of Islamic faith who cannot eat swine, and those of the sacred and inviolable, cannot consume a soft capsule containing such gelatin derived from cattle and/or swine.
- gelatin produced from the bone of cattle there is a perception that there is the possibility of infection with bovine spongiform encephalopathy.
- gelatin other than that derived from cattle and swine, suffers from problems such that the gelatin does not provide the desired strength required for forming a gelatin capsule and it may increase the production cost of the gelatin capsule as its cost is generally higher when compared with the gelatin derived from cattle and swine.
- unmodified starch such as rice starch and corn starch
- a gelling agent and/or a plasticizer suffers from a problem in that it has a high viscosity, and it would be difficult to blend the starch with a gelling agent and/or a plasticizer and that the workability thereof upon the production of capsules is accordingly impaired.
- the strength of a capsule, prepared using corn starch which has been decomposed even to dextrin according to the enzyme treatment as one of the physical treatments to reduce the viscosity is quite low and accordingly, the resulting product (capsule) cannot be used. It further suffers from a problem in that the strength thereof is extremely reduced with the lapse of time.
- the present invention has been completed on the basis of such a finding that acid-decomposed waxy corn starch, among a variety of starches, is suitable as a substitute for gelatin and that when combining waxy corn starch with a gelling agent and a plasticizer, a shell can be formed, which has excellent characteristic properties suitable for use in the preparation of a soft capsule.
- the present invention provides a film-forming composition for use in the preparation of a soft capsule, which comprises (a) acid-decomposed waxy corn starch; (b) a gelling agent; and (c) a plasticizer.
- the present invention also provides a soft capsule which comprises a shell formed from the foregoing composition and a capsule-filling material accommodated within the shell.
- the present invention can provide a shell for soft capsules, which is completely free of any material derived from animals such as gelatin and a soft capsule which comprises the shell and capsule-filling material accommodated within the shell.
- the soft capsule comprising the shell produced using the film-forming composition for soft capsules has excellent characteristic properties with respect to physical strength, disintegration ability, odor, taste, color and lack of stickiness or adhesion; it also has excellent stability with the lapse of time.
- carrageenan as the gelling agent (b) would have an advantage in that a film having a strength sufficient for processing and forming into a capsule can be formed without using any metal salt (such as a sodium salt, a potassium salt or a calcium salt), which salts are in general required for the gelatinization of carrageenan.
- metal salt such as a sodium salt, a potassium salt or a calcium salt
- Corn can be divided into species of dent corn and waxy corn, but the starch derived from the corn belonging to the waxy corn species is the objective starch to be used in the present invention as the component (a).
- the corn of the waxy species is also referred to as glutinous corn, and the starch derived therefrom is generally one which is free of any amylase and substantially comprises 100% amylopectin.
- the acid-decomposed waxy corn starch used in the present invention includes acid hydrolyzed waxy corn starch and acid roasted or broiled waxy corn starch.
- the acid-decomposed waxy corn starch suitable for use in the present invention can be made according to known processes or purchased from commercial sources.
- the acid-decomposed waxy corn starch is, for instance, one obtained by adding an inorganic acid or an organic acid such as sulfuric acid, or an oxidizing agent such as sodium hypochlorite to the starch derived from the corn of the waxy species and then heating the resulting mixture at a temperature ranging from about 10 to about 160°C to thus partially decompose the starch structure.
- an inorganic acid or an organic acid such as sulfuric acid, or an oxidizing agent such as sodium hypochlorite
- those preferably used in the present invention are those having a content of carboxyl groups on the order of not higher than 0.1% by mass.
- preferably used herein are those each having a viscosity ranging from about 5 to about 100 mPa ⁇ S, as determined at 80°C using a 20% by mass aqueous solution thereof.
- the viscosity of the starch can be determined using a BM viscometer (VISCO-BM Model, available from TOKIMECH Co., Ltd.) and a rotor no. 1.
- the acid-decomposed waxy corn starch is commercially available as, for instance, WS-10 (available from MATSUTANI Chemical Industry, Co., Ltd.).
- Particularly preferred acid-decomposed waxy corn starches include those having a viscosity ranging from about 5 to about 50 mPa ⁇ S and more preferably about 10 to about 20 mPa ⁇ S, as determined under the foregoing conditions.
- the amount of the acid-decomposed waxy corn starch as the component (a) used in the film-forming composition for soft capsules according to the present invention preferably ranges from about 10 to about 60% by mass and more preferably about 25 to about 60% by mass (on the basis of the dry mass of the composition or the mass thereof except for water).
- Examples of the gelling agents as the component (b) used in the present invention are carrageenan (i- carrageenan, ⁇ -carrageenan and ⁇ -carrageenan), agar, gum arabic, gellan gum, native gellan gum, pullulan, pectin, glucomannan, locust bean gum, guar gum, geran gum, cellulose, konjak-derived gum, furcellaran, tara-derived (Japanese angelica), i- carrageenan, ⁇ -carrageenan and ⁇ -carrageenan), agar, gum arabic, gellan gum, native gellan gum, pullulan, pectin, glucomannan, locust bean gum, guar gum, geran gum, cellulose, konjak-derived gum, furcellaran, tara-derived (Japanese angelica
- carrageenan i- carrageenan, ⁇ -carrageenan and ⁇ -carrageenan
- agar gum arabic, gellan gum, native gellan gum, pullulan, pectin and glucomannan
- gelling agents are i- carrageenan, ⁇ -carrageenan and mixtures thereof, among others.
- the amount of the gelling agent used as the component (b) of the film-forming composition for soft capsules according to the present invention preferably ranges from about 8 to about 30% by mass and more preferably about 10 to about 24% by mass (on the basis of the dry mass of the composition or the mass thereof except for water).
- plasticizers used in the composition of the present invention as the component (c) include glycerin, sorbitol, maltitol, propylene glycol, polyethylene glycol, sugar alcohol, lactitol, polyalkylene glycol, monosaccharides, disaccharides,
- oligosaccharides isomalto-oligosaccharides, diethylene glycol, glycerol monoacetate, glycerol diacetate, glycerol triacetate, invert sugars, corn syrup and 1 ,2-propylene glycol, which may be used alone or in any combination of at least two of them.
- preferably used herein include glycerin, sorbitol, maltitol, propylene glycol, polyethylene glycol, sugar alcohol, lactitol, polyalkylene glycol, monosaccharides, disaccharides, oligosaccharides and isomalto-oligo- saccharides, which may be used alone or in any combination of at least two of them.
- plasticizer (c) are glycerin, sorbitol, polyethylene glycol and mixtures thereof.
- the amount of the plasticizer as the component (c) used in the film-forming composition for soft capsules according to the present invention preferably ranges from about 5 to about 65% by mass, more preferably about 10 to about 60% by mass and particularly preferably about 15 to about 50% by mass (on the basis of the dry mass of the composition or the mass thereof except for water).
- the film-forming composition for soft capsules according to the present invention may further comprise a buffering agent (d).
- buffering agents are sodium salts, potassium salts and calcium salts, and the buffering agent (d) used in the invention is preferably sodium phosphate.
- the amount of the buffering agent as the component (d) used in the film-forming composition for soft capsules according to the present invention preferably ranges from about 0.2 to about 5% by mass and more preferably about 1 to about 4% by mass (on the basis of the dry mass of the composition or the mass thereof except for water).
- carrageenan is particularly preferably used as the gelling agent or the component (b) since this would permit the elimination of the need for any buffering agent such as sodium salts, potassium salts and calcium salts, which are in general required for the gelatinization of carrageenan.
- the film-forming composition for soft capsules according to the present invention may further comprise, as optional components, other additives, for instance, a coloring agent such as a coloring dyestuff or a pigment, a perfume and/or a preservative.
- a coloring agent such as a coloring dyestuff or a pigment
- a perfume and/or a preservative it is preferred that the composition is completely free of gelatin.
- the film-forming composition for soft capsules When forming a shell for soft capsules using the film-forming composition for soft capsules according to the present invention, it is suitable that water is added to and blended with the film-forming composition for soft capsules in an amount ranging from about 40 to about 110 parts by mass per 100 parts by mass of the film-forming composition, and the resulting blend is then formed into a shell according to the usual method in such a manner that the thickness of the shell is set at a level ranging from about 0.1 to about 1.0 mm. In this respect, it is also possible to form a seamless capsule with the use of the film-forming composition for soft capsules according to the present invention. Methods of making soft capsules are conventional and can readily be used with the film-forming composition of the present invention.
- the soft capsule of the present invention may be filled with, for instance, a suspension or an oil as a capsule-filling material. One of ordinary skill in the art can readily determine a suitable fill material.
- Example 3 In these Comparative Examples 3 to 5, the same procedures used in Example 1 were repeated except that cluster dextrin (derived from waxy corn; Comparative Example 3), enzyme-treated dextrin (Pinedex #100; Comparative Example 4) and enzyme-treated dextrin
- Example 1 The capsules produced in Example 1 and Comparative Examples 3 to 5 were inspected for the film strength and the stability thereof with the lapse of time, according to the following methods.
- Film Thickness About 0.5 mm (0.4 to 0.6 mm);
- Burst Test Machine KIYA Type Hardness Meter (1600-E Type, available from Fujiwara Seisakusho, Ltd.) Disintegration Ability
- Example 1 the capsules produced in Example 1 and Comparative Examples 3 to 5 were inspected for the characteristic properties such as the appearance of the soft capsules.
- the results thus obtained are summarized in the following Table 5.
- the soft capsule (Example 1) produced using the film-forming composition for soft capsules according to the present invention was found to be excellent in all of the properties tested, or the odor, taste, color and lack of clumping, while the capsule prepared in Comparative Example 3 gives out a strong odor of caramel and has a taste of caramel. Accordingly, a problem arises such that the odor of caramel may impair the palatability of the capsule when eating the same.
- the capsule prepared in Comparative Example 4 suffers from such a problem that it has an insufficient transparency and appears to be dark, although it has weak odor and taste of caramel.
- the capsule prepared in Comparative Example 5 has an insufficient transparency, appears to be dark. Further the capsules prepared in Comparative Example 5 are mutually adhered to one another strongly, causing clumping and a problem thus arises when packaging the same.
- Example 2 The same procedures used in Example 1 were repeated except for using the composition specified in the following Table 6, or the film-forming composition for soft capsules used in Example 1, from which sodium phosphate as a buffering agent was removed, to thus form a soft capsule.
- the present invention permits the production of a soft capsule with excellent physical strength without using sodium phosphate as a buffering agent. Moreover, when comparing the results listed in Table 3 with those listed in Table 7, it was found that the capsule prepared in Example 2 has a shorter opening time than that observed for the capsule prepared in Example 1 , and the former has an excellent disintegration rate, which is one of the advantages of the soft capsule.
Abstract
Description
Claims
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BR112013002721A BR112013002721B8 (en) | 2010-08-04 | 2010-08-04 | film-forming composition for soft capsules, soft capsules and their shell |
US13/814,168 US20130189522A1 (en) | 2010-08-04 | 2010-08-04 | Film-forming composition for soft capsules |
EP10855698.6A EP2600849B1 (en) | 2010-08-04 | 2010-08-04 | Film-forming composition for soft capsules |
CA2807314A CA2807314C (en) | 2010-08-04 | 2010-08-04 | Film-forming composition for soft capsules |
KR1020127015423A KR101288079B1 (en) | 2010-08-04 | 2010-08-04 | Film-forming composition for soft capsules |
MX2013001311A MX344742B (en) | 2010-08-04 | 2010-08-04 | Film-forming composition for soft capsules. |
PCT/US2010/044419 WO2012018329A1 (en) | 2010-08-04 | 2010-08-04 | Film-forming composition for soft capsules |
AU2010358565A AU2010358565B2 (en) | 2010-08-04 | 2010-08-04 | Film-forming composition for soft capsules |
CN201080069480.7A CN103228269B (en) | 2010-08-04 | 2010-08-04 | Film-forming composition for soft capsules |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/US2010/044419 WO2012018329A1 (en) | 2010-08-04 | 2010-08-04 | Film-forming composition for soft capsules |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2012018329A1 true WO2012018329A1 (en) | 2012-02-09 |
Family
ID=45559704
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2010/044419 WO2012018329A1 (en) | 2010-08-04 | 2010-08-04 | Film-forming composition for soft capsules |
Country Status (9)
Country | Link |
---|---|
US (1) | US20130189522A1 (en) |
EP (1) | EP2600849B1 (en) |
KR (1) | KR101288079B1 (en) |
CN (1) | CN103228269B (en) |
AU (1) | AU2010358565B2 (en) |
BR (1) | BR112013002721B8 (en) |
CA (1) | CA2807314C (en) |
MX (1) | MX344742B (en) |
WO (1) | WO2012018329A1 (en) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014209964A1 (en) * | 2013-06-25 | 2014-12-31 | R.P. Scherer Technologies, Llc | Shell-forming compositions for soft capsules and soft capsules |
US9408858B2 (en) | 2007-04-25 | 2016-08-09 | Opko Renal, Llc | Method for treating secondary hyperparathyroidism in CKD |
US9861644B2 (en) | 2013-03-15 | 2018-01-09 | Opko Ireland Global Holdings, Ltd. | Stabilized modified release vitamin D formulation and method of administering same |
US9943530B2 (en) | 2006-02-03 | 2018-04-17 | Opko Renal, Llc | Treating vitamin D insufficiency and deficiency with 25-hydroxyvitamin D2 and 25-hydroxyvitamin D3 |
US10220047B2 (en) | 2014-08-07 | 2019-03-05 | Opko Ireland Global Holdings, Ltd. | Adjunctive therapy with 25-hydroxyvitamin D and articles therefor |
US10302660B2 (en) | 2008-04-02 | 2019-05-28 | Opko Renal, Llc | Methods useful for vitamin D deficiency and related disorders |
US10668089B2 (en) | 2006-06-21 | 2020-06-02 | Opko Ireland Global Holdings, Ltd. | Method of treating and preventing secondary hyperparathyroidism |
US11173168B2 (en) | 2016-03-28 | 2021-11-16 | Eirgen Pharma Ltd. | Methods of treating vitamin D insufficiency in chronic kidney disease |
US11672809B2 (en) | 2010-03-29 | 2023-06-13 | Eirgen Pharma Ltd. | Methods and compositions for reducing parathyroid levels |
US11752158B2 (en) | 2007-04-25 | 2023-09-12 | Eirgen Pharma Ltd. | Method of treating vitamin D insufficiency and deficiency |
US11801253B2 (en) | 2007-04-25 | 2023-10-31 | Opko Renal, Llc | Method of safely and effectively treating and preventing secondary hyperparathyroidism in chronic kidney disease |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103893771B (en) | 2014-04-21 | 2015-08-26 | 湖南尔康制药股份有限公司 | A kind of film-forming composition for the production of starch material soft capsule and preparation method thereof |
US20170292011A1 (en) * | 2014-10-03 | 2017-10-12 | Fuji Capsule Co., Ltd. | Soft capsule shell |
KR101675438B1 (en) | 2015-12-18 | 2016-11-11 | 김문구 | Composition for preparing soft capsule shell |
US10711119B2 (en) * | 2018-01-10 | 2020-07-14 | Cp Kelco Aps | Carrageenan-based compositions for films and capsules |
CN109908102B (en) * | 2018-12-28 | 2019-12-27 | 中国科学院化学研究所 | Shell forming composition for preparing plant soft capsules and method for preparing soft capsules |
CN116531343B (en) * | 2023-05-16 | 2023-12-01 | 秦皇岛稷中食品有限公司 | Gelling composition containing carrageenan and preparation method thereof |
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US6214376B1 (en) * | 1998-08-25 | 2001-04-10 | Banner Pharmacaps, Inc. | Non-gelatin substitutes for oral delivery capsules, their composition and process of manufacture |
US6375981B1 (en) * | 2000-06-01 | 2002-04-23 | A. E. Staley Manufacturing Co. | Modified starch as a replacement for gelatin in soft gel films and capsules |
US20050196436A1 (en) * | 2004-03-02 | 2005-09-08 | Arjnarong Chantranukul | Blends of different acyl gellan gums and starch |
US20080138402A1 (en) * | 2006-11-17 | 2008-06-12 | Zhixin Li | Highly inhibited starch fillers for films and capsules |
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SI1105107T1 (en) * | 1999-07-07 | 2007-04-30 | Scherer Technologies Inc R P | Film forming compositions comprising modified starches and iota-carrageenan and methods for manufacturing soft capsules using same |
US6528088B1 (en) * | 2000-06-01 | 2003-03-04 | A. E. Staley Manufacturing Co. | Highly flexible starch-based films |
US8231896B2 (en) * | 2004-11-08 | 2012-07-31 | R.P. Scherer Technologies, Llc | Non-gelatin soft capsule system |
CN101203551B (en) * | 2005-06-16 | 2011-09-28 | 日本合成化学工业株式会社 | Water-solubility membrane |
-
2010
- 2010-08-04 CN CN201080069480.7A patent/CN103228269B/en active Active
- 2010-08-04 MX MX2013001311A patent/MX344742B/en active IP Right Grant
- 2010-08-04 AU AU2010358565A patent/AU2010358565B2/en active Active
- 2010-08-04 KR KR1020127015423A patent/KR101288079B1/en active IP Right Grant
- 2010-08-04 EP EP10855698.6A patent/EP2600849B1/en active Active
- 2010-08-04 US US13/814,168 patent/US20130189522A1/en not_active Abandoned
- 2010-08-04 WO PCT/US2010/044419 patent/WO2012018329A1/en active Application Filing
- 2010-08-04 BR BR112013002721A patent/BR112013002721B8/en active IP Right Grant
- 2010-08-04 CA CA2807314A patent/CA2807314C/en active Active
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US6214376B1 (en) * | 1998-08-25 | 2001-04-10 | Banner Pharmacaps, Inc. | Non-gelatin substitutes for oral delivery capsules, their composition and process of manufacture |
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US20050196436A1 (en) * | 2004-03-02 | 2005-09-08 | Arjnarong Chantranukul | Blends of different acyl gellan gums and starch |
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Cited By (29)
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US11911398B2 (en) | 2006-02-03 | 2024-02-27 | Opko Renal, Llc | Treating Vitamin D insufficiency and deficiency with 25-hydroxyvitamin D2 and 25-hydroxyvitamin D3 |
US11007204B2 (en) | 2006-02-03 | 2021-05-18 | Opko Renal, Llc | Treating vitamin D insufficiency and deficiency with 25-hydroxyvitamin D2 and 25-hydroxyvitamin D3 |
US10213442B2 (en) | 2006-02-03 | 2019-02-26 | Opko Renal, Llc | Treating vitamin D insufficiency and deficiency with 25-hydroxyvitamin D2 and 25-hydroxyvitamin D3 |
US9943530B2 (en) | 2006-02-03 | 2018-04-17 | Opko Renal, Llc | Treating vitamin D insufficiency and deficiency with 25-hydroxyvitamin D2 and 25-hydroxyvitamin D3 |
US10668089B2 (en) | 2006-06-21 | 2020-06-02 | Opko Ireland Global Holdings, Ltd. | Method of treating and preventing secondary hyperparathyroidism |
US9925147B2 (en) | 2007-04-25 | 2018-03-27 | Opko Renal, Llc | Method for treating secondary hyperparathyroidism in CKD |
US11154509B2 (en) | 2007-04-25 | 2021-10-26 | Eirgen Pharma Ltd. | Methods for controlled release oral dosage of a vitamin D compound |
US9918940B2 (en) | 2007-04-25 | 2018-03-20 | Opko Renal, Llc | Methods for controlled release oral dosage of a vitamin D compound |
US9498486B1 (en) | 2007-04-25 | 2016-11-22 | Opko Renal, Llc | Method for controlled release oral dosage of a vitamin D compound |
US9408858B2 (en) | 2007-04-25 | 2016-08-09 | Opko Renal, Llc | Method for treating secondary hyperparathyroidism in CKD |
US11752158B2 (en) | 2007-04-25 | 2023-09-12 | Eirgen Pharma Ltd. | Method of treating vitamin D insufficiency and deficiency |
US11801253B2 (en) | 2007-04-25 | 2023-10-31 | Opko Renal, Llc | Method of safely and effectively treating and preventing secondary hyperparathyroidism in chronic kidney disease |
US10302660B2 (en) | 2008-04-02 | 2019-05-28 | Opko Renal, Llc | Methods useful for vitamin D deficiency and related disorders |
US11672809B2 (en) | 2010-03-29 | 2023-06-13 | Eirgen Pharma Ltd. | Methods and compositions for reducing parathyroid levels |
US9861644B2 (en) | 2013-03-15 | 2018-01-09 | Opko Ireland Global Holdings, Ltd. | Stabilized modified release vitamin D formulation and method of administering same |
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EP2600849B1 (en) | 2016-03-30 |
US20130189522A1 (en) | 2013-07-25 |
BR112013002721B8 (en) | 2021-05-25 |
CA2807314A1 (en) | 2012-02-09 |
AU2010358565B2 (en) | 2016-07-14 |
CN103228269B (en) | 2015-06-17 |
KR20120128602A (en) | 2012-11-27 |
MX344742B (en) | 2017-01-05 |
KR101288079B1 (en) | 2013-07-22 |
CA2807314C (en) | 2017-06-20 |
EP2600849A4 (en) | 2014-01-15 |
MX2013001311A (en) | 2013-03-18 |
CN103228269A (en) | 2013-07-31 |
AU2010358565A1 (en) | 2013-02-14 |
BR112013002721B1 (en) | 2020-12-15 |
BR112013002721A2 (en) | 2016-05-31 |
EP2600849A1 (en) | 2013-06-12 |
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