WO2004024138A1 - Preparation solide contenant du sulfosuccinate de dioctyl sodium - Google Patents
Preparation solide contenant du sulfosuccinate de dioctyl sodium Download PDFInfo
- Publication number
- WO2004024138A1 WO2004024138A1 PCT/JP2003/011585 JP0311585W WO2004024138A1 WO 2004024138 A1 WO2004024138 A1 WO 2004024138A1 JP 0311585 W JP0311585 W JP 0311585W WO 2004024138 A1 WO2004024138 A1 WO 2004024138A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- solid preparation
- mass
- enteric coating
- core particles
- preparation according
- Prior art date
Links
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 title claims abstract description 33
- CDOUZKKFHVEKRI-UHFFFAOYSA-N 3-bromo-n-[(prop-2-enoylamino)methyl]propanamide Chemical compound BrCCC(=O)NCNC(=O)C=C CDOUZKKFHVEKRI-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- 239000007787 solid Substances 0.000 title claims abstract description 17
- 239000008187 granular material Substances 0.000 claims abstract description 18
- 239000007771 core particle Substances 0.000 claims abstract description 17
- 239000000843 powder Substances 0.000 claims abstract description 13
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 18
- 239000002702 enteric coating Substances 0.000 claims description 17
- 238000009505 enteric coating Methods 0.000 claims description 17
- 150000008064 anhydrides Chemical class 0.000 claims description 9
- 235000019359 magnesium stearate Nutrition 0.000 claims description 9
- 229920003145 methacrylic acid copolymer Polymers 0.000 claims description 5
- 229940117841 methacrylic acid copolymer Drugs 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 239000003518 caustics Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- 229920000623 Cellulose acetate phthalate Polymers 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 229940081734 cellulose acetate phthalate Drugs 0.000 claims description 2
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 claims description 2
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 claims description 2
- 229920000639 hydroxypropylmethylcellulose acetate succinate Polymers 0.000 claims 1
- 210000002429 large intestine Anatomy 0.000 abstract description 6
- 210000001035 gastrointestinal tract Anatomy 0.000 abstract description 2
- 230000001543 purgative effect Effects 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- 230000002349 favourable effect Effects 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- -1 hydroxypropyl methyl Chemical group 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 3
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 3
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- WQNHWIYLCRZRLR-UHFFFAOYSA-N 2-(3-hydroxy-2,5-dioxooxolan-3-yl)acetic acid Chemical compound OC(=O)CC1(O)CC(=O)OC1=O WQNHWIYLCRZRLR-UHFFFAOYSA-N 0.000 description 2
- HWMMCEJITBPQBR-UHFFFAOYSA-N CCCCCCCC[Na] Chemical compound CCCCCCCC[Na] HWMMCEJITBPQBR-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 238000007922 dissolution test Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 210000000936 intestine Anatomy 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 239000008141 laxative Substances 0.000 description 2
- 230000002475 laxative effect Effects 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 229920003169 water-soluble polymer Polymers 0.000 description 2
- TVZRAEYQIKYCPH-UHFFFAOYSA-N 3-(trimethylsilyl)propane-1-sulfonic acid Chemical compound C[Si](C)(C)CCCS(O)(=O)=O TVZRAEYQIKYCPH-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000001836 Dioctyl sodium sulphosuccinate Substances 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 1
- IYKJEILNJZQJPU-UHFFFAOYSA-N acetic acid;butanedioic acid Chemical compound CC(O)=O.OC(=O)CCC(O)=O IYKJEILNJZQJPU-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229940031703 low substituted hydroxypropyl cellulose Drugs 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229940126701 oral medication Drugs 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/225—Polycarboxylic acids
-
- 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
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5005—Wall or coating material
- A61K9/5021—Organic macromolecular compounds
- A61K9/5026—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/10—Laxatives
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1611—Inorganic compounds
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1617—Organic compounds, e.g. phospholipids, fats
Definitions
- the present invention relates to a formulation containing dioctyl sodizulfosuccinate.
- Dioctylsodium sulfosuccinate is known as a laxative. Its effect is to act directly on hard stools in the intestine to penetrate water, soften and swell the stool, thereby promoting excretion.
- dioctylsodium sulfosuccinate is a waxy substance, it is known that it is difficult to prepare a general colon-proximal release-type preparation coated with an enteric coating or the like. Therefore, an oral drug containing conventional dioctylsodium sulfosuccinate is not effective as a direct effect because it is released at the upper part of the digestive tract after oral administration.
- An object of the present invention is to provide a solid preparation in which dioctylsodium sulfosuccinate is released in the vicinity of the large intestine at the site of action and has an effective cathartic effect. Disclosure of the invention
- the present inventors have conducted various studies to solve the problems, and as a result, granulated a powder containing dioctylsodium sulphosuccinate and light citric anhydride, and produced the obtained granules or the granules.
- an enteric coating By applying an enteric coating to the tablet obtained in this manner, it was found that an excellent preparation in which dimethyltyl sulfosuccinate was released in the vicinity of the large intestine was obtained, and the present invention was completed. That is, the present invention is a solid preparation characterized in that an enteric coating is applied to core particles containing dioctylsodium sulfosuccinate and light citric anhydride.
- the core particle is an object to be coated with an enteric coating, and is a granule obtained by kneading and granulating a powder containing dioctylsodium sulfosuccinate and light gay anhydride, or a tablet thereof. Tablets and the like can be used.
- magnesium stearate it is preferable to mix magnesium stearate with light gay anhydride at the same time in view of workability at the time of tableting.
- the enteric coating may be any of those commonly used for enteric coating, and particularly, methacrylic acid copolymer (L, S, LD), hydroxypropyl methylcellulose phthalate, hydroxypropyl methyl Cell opening—A component selected from the group consisting of acetate succinate, carboxymethylethyl cellulose and cellulose acetate phthalate is preferred. They can be used alone or as a mixture of two or more.
- the coating amount when the enteric coating is directly coated on the core particles is preferably 1 to 30% by mass based on the mass of the core particles.
- an enteric capsule may be used as the enteric coating.
- the granules of the core particles are filled into an enteric capsule to form a capsule.
- dioctyl sodizulfosuccinate and other active ingredients having a purging action in the same granules or in separate granules, and to mix them and blend them, since the purging action can be expected to be improved, which is preferable.
- Pisacodyl is preferable as another active ingredient having a purgative effect in terms of the effect, and its compounding amount is preferably 3 to 15 mg in a daily dose.
- pisacodyl was hardly soluble, so that sufficient effects could not be obtained even when it was added to the preparation.
- visacodyl was simultaneously added to dioctyl sodium sulfosuccinate. It has also been found that this improves the solubility. Therefore, synergistic effects can be expected by simultaneously combining visacodyl and dioctylsodium sulfosuccinate in the present invention as compared with the case where each is administered alone. Therefore, in the present invention, a formulation in which pisacodyl is simultaneously added to the core particles is more preferable.
- a solvent in which dioctylsodium sulfosuccinate is dissolved It is preferable to mix a hydrophilic polymer in terms of the properties of the obtained granules.
- water-soluble polymer to be blended here those usually used as a binder can be used. Preferred examples thereof include hydroxypropylcellulose, polyvinylpyrrolidone and hydroxypropylmethylcell mouth.
- the mixing amount of the water-soluble polymer is preferably from 0.1 to 0.3 part by mass with respect to 1 part by mass of octylsodium sulfosuccinate.
- 0.5 to 1.5 parts by weight, preferably 0.6 to 1.3 parts by weight, of light gay anhydride is preferably added to 1 part by weight of dioctylsodium sulfosuccinate. More preferred. If the amount is more than 1.5 parts by mass, an excessive fine powder resulting from excess light acid anhydride may cause trouble during tableting.
- magnesium stearate is preferably used in an amount of from 0.05 to 0.5 part by mass, more preferably from 0.1 to 0.3 part by mass, per part by mass of dioctylsodium sulfosuccinate.
- the core particles of the present invention are produced as follows.
- Dioctylsodium sulfosuccinate is dissolved in a solvent such as water or ethanol to form a solution.
- the solution is added while spraying or all at once, and a powder obtained by mixing light caustic anhydride and, if necessary, magnesium stearate is granulated to obtain a powder.
- FIG. 1 is a diagram showing the results of a dissolution test of Examples and Comparative Examples, in which the vertical axis represents the dissolution rate, and the horizontal axis represents time and pH.
- 960 g of dioctylsodium sulfosuccinate and 200 g of hydroxypropylcellulose were dissolved in alcohol, and mixed with 960 g of light caustic anhydride and 288 g of magnesium stearate. After kneading and granulating with the powder, drying and sizing, granules B were obtained. Granule A, Granule B, 30 g of magnesium stearate and 30 g of light anhydrous calcium acid were added and mixed. The obtained granules were tableted to give tablets having a tablet diameter of 5 mm and a tablet weight of 5 O mg. This was used as a nuclear particle.
- Test example 1 A core particle tablet produced in the same manner as in Example 1 was used as a comparative example.
- Test example 1 A core particle tablet produced in the same manner as in Example 1 was used as a comparative example.
- DSS Dioctyl sodium sulfosuccinate Coexistence of hosuccinate as evident from the table Showed that the solubility of pisacodyl was significantly improved.
- the present invention makes it possible to efficiently release dioctylsodium sulfosuccinate into the vicinity of the large intestine, which is the site of action, and is therefore useful as an effective laxative.
Landscapes
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Emergency Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
La présente invention concerne le sulfosuccinate de dioctyl sodium, qui est une substance cireuse difficile à traiter en une préparation commune enrobée d'un film gastro-résistant ou analogue qui permettrait sa libération aux environs du gros intestin, de sorte qu'elle est libérée dans la partie supérieure des voies digestives et que, par conséquent, elle ne déploie pas une action directe d'une grande efficacité. L'invention concerne une préparation solide à partir de laquelle le sulfosuccinate de dioctyl sodium est libéré aux alentours du gros intestin (c'est-à-dire du site d'action) afin de pouvoir exercer un effet purgatif bénéfique. L'invention se rapporte en particulier à une préparation solide caractérisée en ce que des particules noyaux contenant des granulés, que l'on obtient en granulant une poudre contenant un anhydride silicique léger à l'aide d'une solution contenant du sulfosuccinate de dioctyl sodium, sont enrobées dans un film gastro-résistant.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2004535937A JPWO2004024138A1 (ja) | 2002-09-10 | 2003-09-10 | ジオクチルソジウムスルホサクシネート配合固形製剤 |
| AU2003262060A AU2003262060A1 (en) | 2002-09-10 | 2003-09-10 | Solid preparation containing dioctyl sodium sulfosuccinate |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002-264688 | 2002-09-10 | ||
| JP2002264688 | 2002-09-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2004024138A1 true WO2004024138A1 (fr) | 2004-03-25 |
Family
ID=31986541
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP2003/011585 WO2004024138A1 (fr) | 2002-09-10 | 2003-09-10 | Preparation solide contenant du sulfosuccinate de dioctyl sodium |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPWO2004024138A1 (fr) |
| AU (1) | AU2003262060A1 (fr) |
| WO (1) | WO2004024138A1 (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007055969A (ja) * | 2005-08-26 | 2007-03-08 | Taisho Pharmaceut Co Ltd | ビサコジルの溶出性向上剤 |
| JP2012514624A (ja) * | 2009-01-09 | 2012-06-28 | フォーワード・ファルマ・アクティーゼルスカブ | 浸食マトリックス中に１またはそれ以上のフマル酸エステルを含む医薬製剤 |
| JP2018507209A (ja) * | 2015-02-20 | 2018-03-15 | サイテック インダストリーズ インコーポレイテッド | ジアルキルスルホスクシナート組成物、製造方法、および使用方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5799521A (en) * | 1980-12-11 | 1982-06-21 | Eisai Co Ltd | Solid composition containing bisacodyl |
| JPH02255613A (ja) * | 1989-03-27 | 1990-10-16 | Lion Corp | ジオクチルソジウムスルホサクシネート配合製剤 |
| US5843479A (en) * | 1993-02-26 | 1998-12-01 | The Procter & Gamble Company | Bisacodyl dosage form with multiple enteric polymer coatings for colonic delivery |
-
2003
- 2003-09-10 AU AU2003262060A patent/AU2003262060A1/en not_active Abandoned
- 2003-09-10 JP JP2004535937A patent/JPWO2004024138A1/ja active Pending
- 2003-09-10 WO PCT/JP2003/011585 patent/WO2004024138A1/fr active Application Filing
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5799521A (en) * | 1980-12-11 | 1982-06-21 | Eisai Co Ltd | Solid composition containing bisacodyl |
| JPH02255613A (ja) * | 1989-03-27 | 1990-10-16 | Lion Corp | ジオクチルソジウムスルホサクシネート配合製剤 |
| US5843479A (en) * | 1993-02-26 | 1998-12-01 | The Procter & Gamble Company | Bisacodyl dosage form with multiple enteric polymer coatings for colonic delivery |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007055969A (ja) * | 2005-08-26 | 2007-03-08 | Taisho Pharmaceut Co Ltd | ビサコジルの溶出性向上剤 |
| JP2012514624A (ja) * | 2009-01-09 | 2012-06-28 | フォーワード・ファルマ・アクティーゼルスカブ | 浸食マトリックス中に１またはそれ以上のフマル酸エステルを含む医薬製剤 |
| US11173123B2 (en) | 2009-01-09 | 2021-11-16 | Biogen Swiss Manufacturing Gmbh | Pharmaceutical formulation comprising one or more fumaric acid esters in an erosion matrix |
| JP2018507209A (ja) * | 2015-02-20 | 2018-03-15 | サイテック インダストリーズ インコーポレイテッド | ジアルキルスルホスクシナート組成物、製造方法、および使用方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPWO2004024138A1 (ja) | 2006-01-05 |
| AU2003262060A1 (en) | 2004-04-30 |
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