WO2015152680A1 - Granule comprising silodosin, and pharmaceutical composition and formulation comprising same - Google Patents
Granule comprising silodosin, and pharmaceutical composition and formulation comprising same Download PDFInfo
- Publication number
- WO2015152680A1 WO2015152680A1 PCT/KR2015/003376 KR2015003376W WO2015152680A1 WO 2015152680 A1 WO2015152680 A1 WO 2015152680A1 KR 2015003376 W KR2015003376 W KR 2015003376W WO 2015152680 A1 WO2015152680 A1 WO 2015152680A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- silodosin
- granule
- stabilizer
- inorganic salt
- formulation
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- 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
- A61K9/1623—Sugars or sugar alcohols, e.g. lactose; Derivatives thereof; Homeopathic globules
-
- 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
- A61K9/1629—Organic macromolecular compounds
- A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2009—Inorganic compounds
Definitions
- the present invention relates to a granule comprising silodosin, and a pharmaceutical composition and a formulation comprising same. More particularly, it relates to a granule comprising silodosin showing improved storage stability, and a pharmaceutical composition and a formulation comprising same.
- Prostatic hypertrophy is a disease showing high incidence in elderly males, and it is estimated that 70% of males in their 60s are suffering from this disease. Due to a recent accelerated ageing of populations, the number of patients with prostatic hypertrophy is increasing rapidly, leading to an increased interest in its therapy.
- the main treatment methods for prostatic hypertrophy include drug therapy and surgical therapy.
- Surgical therapies may include laparotomy with prostatic resection, transurethral resection of the prostate (TUR-P), hyperthermic therapy, laser therapy and stent placement therapy, while drug therapies may include a 1 -adrenergic receptor blockers, anti-androgen drugs and herbal medicine.
- silodosin is an a 1 -adrenergic receptor antagonist as presented in the formula I below (chemical name: l-(3-hydroxypropyl)-5-[(2R)-2-(2-[2-(2,2,2- trifluoroethoxy)phenoxy]ethylamino)propyl]-2,3-dihydro-lH-indole-7-carboxamide).
- Owing to selective inhibition of urethral smooth muscle contraction it decreases pressure inside urethra without significantly affecting blood pressure.
- the selectivity for the a 1 -adrenergic receptor subtype it is very useful in the treatment of urination difficulties and the like, associated with prostatic hypertrophy.
- silodosin is apt to produce various related substances by reactions with a variety of excipients in a pharmaceutical formulation.
- silodosin is known to decrease dissolution characteristics by a reaction with lactose.
- Korean Patent No. 10-1072909 discloses that silodosin produces a variety of related substances by reactions with pharmaceutical excipients including lactose, and that D-mannitol can be used as an excipient to improve its stability.
- D-mannitol some degradation products cannot be avoided, and thus, there is a need for the development of a new composition to improve the stability of silodosin.
- the present inventors have endeavored to improve the stability of silodosin, and found that preparing a granule using alkaline inorganic salt as a stabilizer results in the improvement of its storage stability, dissolution rate and bioavailability.
- a granule comprising: silodosin; an alkaline inorganic salt as a stabilizer; and a pharmaceutically acceptable excipient.
- a pharmaceutical composition comprising the above granule and a pharmaceutically acceptable additive.
- a pharmaceutical formulation prepared by using the above granule or the above pharmaceutical composition.
- the present invention shows that the inventive granules exhibit improved stability for silodosin, and reduction in unwanted reaction of silidosin with other excipients.
- the granule comprising, silidosin of the present invention can be used for the development of a composition or formulation with a variety of dissolution characteristics, without any influence to the stability of silodosin. Also, owing to the decreased adverse effects which may result from degradation products of silodosin, it can be utilized as a safer therapeutic agent for prostatic hypertrophy.
- Fig. 1 is a graph showing the stability of silodosin according to the type of a stabilizer (the amount of related substance I production);
- Fig. 2 is a graph showing the stability of silodosin according to the type of a stabilizer (the amount of total related substance production);
- Fig. 3 is a graph showing the stability of silodosin according to the content of a stabilizer (the amount of related substance I production);
- Fig. 4 is a graph showing the stability of silodosin according to the content of a stabilizer (the amount of total related substance production);
- Fig. 5 is a graph showing the dissolution rate of silodosin according to the content of a stabilizer
- Fig. 6 is a graph showing the stability of silodosin according to the combination of various excipients and stabilizers (the amount of related substance I production);
- Fig. 7 is a graph showing the stability of silodosin according to the combination of various excipients and stabilizers (the amount of total related substance production);
- Fig. 8 is a graph showing the dissolution rate of silodosin according to the type of an excipient
- Fig. 9 is a graph showing the dissolution rate of silodosin according to the difference in preparation method.
- Fig. 10 is a graph comparing the pharmacokinetics of silodosin according to the difference in preparation method.
- the present invention provides a granule comprising silodosin; an alkaline inorganic salt as a stabilizer; and a pharmaceutically acceptable excipient.
- the present invention can improve the stability of silodosin by preparing a granule using an alkaline inorganic salt as a stabilizer.
- the present invention can minimize interactions between silodosin and various pharmaceutical excipients employed in the preparation process of the granule, by preparing the granule using an alkaline inorganic salt as a stabilizer.
- Silodosin employed as an active ingredient in a granule according to the present invention is a compound represented by the formula I, with a chemical name of: l-(3- hydroxypropyl)-5-[(2R)-2-(2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethylamino]propyl]-2,3- dihydro-lH-indole-7-carboxamide. Owing to selective inhibition of urethral smooth muscle contraction, it decreases inner pressure of urethra without significantly affecting blood pressure. Also, owing to the selectivity for the a 1 -adrenergic receptor subtype, it is very useful in the treatment of urination difficulties and the like, associated with prostatic hypertrophy.
- Daily standard dose of silodosin for adults is 1 to 16 mg, which can be administered in an amount of 1 mg, 2 mg, 4 mg, 8 mg, or 16 mg per day.
- An alkaline inorganic salt employed as a stabilizer in a granule according to the present invention can be selected from the group consisting of oxides, hydroxides, carbonates and phosphates of sodium, calcium, potassium, magnesium, manganese, iron, copper, zinc, aluminum and lithium.
- the alkaline inorganic salt can be selected from the group consisting of alkaline metal or alkaline earth metal oxide, hydroxide, carbonate, and phosphate.
- the alkaline inorganic salt can be calcium carbonate (CaC0 3 ), magnesium carbonate (MgC0 3 ), sodium hydrogen carbonate (NaHC0 3 ), or a mixture thereof.
- a stabilizer can be employed in an amount ranging from 0.05 to 33 parts by weight, preferably 0.1 to 10 parts by weight based on 1 part by weight of silodosin.
- the amount of a stabilizer is less than the aforementioned lower limit of the range, the aimed stabilizing effect on silodosin cannot be achieved, while there is a problem that the dissolution rate of silodosin decreases when it exceeds the aforementioned upper limit of the range.
- the aforementioned stabilizer can significantly improve the stability of silodosin as compared to antioxidants (e.g., butylated hydroxyanisole (BHA) or butylated hydroxytoluene (BHT)) or other stabilizers (e.g., meglumine) which are conventionally known to improve the stability of a drug.
- antioxidants e.g., butylated hydroxyanisole (BHA) or butylated hydroxytoluene (BHT)
- other stabilizers e.g., meglumine
- An excipient that can be used in a granule according to the present invention can be at least one selected from the group consisting of a pharmaceutically acceptable diluent, a disintegrant, a plasticizer and a lubricant.
- the diluent can be selected from the group consisting of cellulose powders, microcrystalline cellulose, silicified microcrystalline cellulose, dicalcium phosphate, tricalcium phosphate, mannitol, sorbitol, xylitol, lactose, dextrose, maltose, sucrose, glucose, fructose, maltodextrin, and a mixture thereof, but are not limited thereto.
- the diluent can be employed in an amount ranging from 1 to 99% by weight, preferably 5 to 95% by weight based on the total weight of the granule.
- the disintegrant can be a component that shows stable disintegration, selected from the group consisting of crospovidone, croscarmellose sodium, sodium starch glycolate, low-substituted hydroxypropyl cellulose, starch, alginic acid or its sodium salt, and a mixture thereof, but are not limited thereto.
- the disintegrant can be employed in an amount ranging from 1 to 70% by weight, preferably 2 to 50% by weight based on the total weight of the granule.
- plasticizer examples include polyoxyalkylene (e.g., BASF Pluronics,
- the plasticizer can be employed in an amount ranging from 0.01 to 10% by weight based on the total weight of the granule.
- the lubricant may include stearic acid, magnesium stearate, calcium stearate, talc, sodium stearyl fumarate, silicon dioxide (Si0 2 ), etc., but are not limited thereto.
- the lubricant can be employed in an amount ranging from 0.01 to 10% by weight based on the total weight of the granule.
- a granule according to the present invention can be prepared by granulation processes widely known in the pharmaceutical industry, e.g., a dry granulation process or a wet granulation process.
- a granule according to the present invention can be prepared by a wet granulation process using a mixing granulator or fluidized bed granulator.
- a wet granulation process is generally known to be disadvantageous as compared to a dry granulation process in terms of instability of the drug.
- a granule according to the present invention shows excellent stability, dissolution rate, and bioavailability owing to the effect of the aforementioned stabilizer, although it is prepared by a wet granulation process
- the present invention also provides a pharmaceutical composition
- a pharmaceutical composition comprising the aforementioned granule and a pharmaceutically acceptable additive.
- the additive can be a diluent, a disintegrant, a humectant, a binder or a lubricant.
- the diluent, disintegrant and lubricant are the same as described above.
- humectant may include polyoxyalkylene (e.g., BASF Pluronics, UCC Carboxaxes, PEGs), ether- capped polyoxyalkylene (e.g., polyoxyethylene lauryl ether), ester-capped polyoxyalkylene (e.g., polyoxyethylene stearate), sorbitan stearate, phosphatide, alkyl amine, glycerin, polyethylene oxide, carboxymethyl cellulose, polyvinyl alcohol, polyvinyl pyrrolidone, sodium lauryl sulfate, aryl (C 6 -C 10 ) sulfate salt, etc., but are not limited thereto.
- polyoxyalkylene e.g., BASF Pluronics, UCC Carboxaxes, PEGs
- ether- capped polyoxyalkylene e.g., polyoxyethylene lauryl ether
- ester-capped polyoxyalkylene e.g., polyoxyethylene stea
- the humectant can be employed in an amount ranging from 0.01 to 10%) by weight based on the total weight of the composition.
- the binder can be selected from the group consisting of hydroxypropyl cellulose, hypromellose, polyvinyl pyrrolidone, copovidone, macrogol, silicate derivatives such as light anhydrous silicic acid, synthetic calcium aluminum silicate or magnesium metasilicate aluminate (magnesium aluminum silicate), phosphates such as calcium phosphate dihydrate, carbonates such as calcium carbonate, and a mixture thereof, but are not limited thereto.
- the binder can be employed in an amount ranging from 0.3 to 30% by weight, preferably 1 to 20% by weight based on the total weight of the composition.
- the present invention provides a pharmaceutical formulation prepared by using the aforementioned granule or aforementioned pharmaceutical composition.
- a pharmaceutical formulation of the present invention can be a formulation for oral administration, such as a tablet or capsule.
- the aforementioned granule or pharmaceutical composition can be manufactured into a tablet by a tablet compression process using conventional rotary press, etc.; and preferably into a coated tablet by a light-shielded coating process.
- the aforementioned granules or pharmaceutical composition can be manufactured into a capsule by filling it into a capsule using a conventional capsule filler.
- the capsule may be a hard capsule made of HPMC, gelatin, etc.
- magnesium stearate as a lubricant
- a surfactant e.g., sodium lauryl sulfate (SLS)
- SLS sodium lauryl sulfate
- the present invention provides a method for preparing the aforementioned granule comprising:
- silodosin an alkaline inorganic salt as a stabilizer, and a pharmaceutically acceptable excipient, to prepare a granule by a dry granulation process or wet granulation process.
- the present invention provides a method for preparing a pharmaceutical composition or pharmaceutical formulation, comprising the steps of: (a) mixing silodosin, an alkaline inorganic salt as a stabilizer, and a pharmaceutically acceptable excipient, to prepare a granule by a dry granulation process or wet granulation process; and
- step (b) adding a pharmaceutically acceptable additive to the granule of step (a) to obtain a formulation.
- compositions shown in Table 1 granules comprising silodosin were prepared by a dry granulation method, which were then filled into capsules.
- silodosin (Dongwoo Syntech Ltd., Korea) as an active ingredient; lactose as an excipient; pregelatinized starch as a disintegrant; and calcium carbonate (CaC0 3 ), magnesium carbonate (MgC0 3 ) or sodium hydrogen carbonate (NaHC0 3 ), respectively as a stabilizer, were mixed using High Speed Mixer (Sejong, Korea; Agitator 126 ⁇ 10 rpm, Chopper 3000 ⁇ 300 rpm, kneading time 2 ⁇ 1 min). The mixture was dried to reach a water content of 2.0 ⁇ 0.
- Comparative Examples 1 to 4 Preparation of silodosin formulations with different stabilizers According to the compositions shown in Table 1, capsule formulations of
- Comparative Examples 1 to 3 were prepared by repeating the procedure of Example 1, except for using butylated hydroxyanisole (BHA) or butylated hydroxytoluene (BHT) as antioxidants, or meglumine as another stabilizer, instead of the stabilizer used in Example 1. Meanwhile, in case of Comparative Example 4, a capsule formulation was prepared without using a stabilizer or antioxidant. [Table 1]
- Experimental Example 1 Storage stability of the formulations according to the type of a stabilizer
- the formulations of Examples 1 to 3 and Comparative Examples 1 to 4 were placed in sealed HDPE bottles and stored under the condition of about 60 °C. Then, the amount of related substances was measured as described below, at week 1, 2, and 4.
- silodosin standard preparation
- methanol was added up to a marked line. After accurately taking 1 mL of this solution, methanol was added thereto to reach the final volume of 100 mL, which was then filtered through a 0.45 ⁇ membrane filter to obtain a standard solution.
- methanol was added thereto to reach the final volume of 100 mL each, which were then filtered with a 0.45 ⁇ membrane filter to obtain sample solutions.
- UV-absorption detector (absorbance at 225 nm)
- the peaks of related substances at RRT (relative peak retention time) of 1.34 relative to the peak area of main ingredient were measured at initial preparation, and at week 1, 2, and 4, sequentially.
- alkaline inorganic salt such as calcium carbonate, magnesium carbonate or sodium hydrogen carbonate
- the amount of related substance was significantly smaller than Comparative Example 4, in which no stabilizers or antioxidants was used.
- the amount of related substance production was significantly smaller than Comparative Examples 1 to 3, in which BHA, BHT, or meglumine was used.
- silodosin can be improved by using an alkaline inorganic salt (e.g., calcium carbonate, magnesium carbonate or sodium hydrogen carbonate) as a stabilizer.
- an alkaline inorganic salt e.g., calcium carbonate, magnesium carbonate or sodium hydrogen carbonate
- calcium carbonate was the most preferred as a stabilizer.
- capsule formulations employing various amounts of calcium carbonate were prepared according to the compositions of Table 3.
- the capsules were prepared by the method described in Examples 1 to 3.
- Experimental Example 2 Storage stability of the formulations according to the content of a stabilizer Using the capsule formulations of Examples 4 to 9, the amount of related substance was measured by the same method as Experimental Example 1. The results are shown in Table 4 and Figs. 3 and 4.
- Example 1 it was found that the capsule formulations of the present invention which comprise an alkaline inorganic salt as a stabilizer (Examples 4 to 9) had significantly superior storage stability as compared to the capsule formulations which do not comprise the stabilizer (Comparative Examples 1 to 4).
- Example 4 which employs a stabilizer in an amount of 0.025 part by weight based on 1 part by weight of silodosin
- Example 5 to 9 which employ a stabilizer in an amount of at least 0.1 part by weight.
- a stabilizer in an amount of at least 0.1 part by weight based on 1 part by weight of silodosin, in order to maximize the stabilizing effect of the stabilizer on the formulation comprising silodosin.
- Experimental Example 3 Dissolution test of silodosin according to the content of a stabilizer
- Silodosin is known to generate a number of degradation products by reactions with a variety of excipients.
- capsule formulations were prepared using various excipients, according to the compositions of Table 6. The capsules were prepared by the methods described in Examples 1 to 3.
- Comparative Examples 5 to 8 Preparation of silodosin formulation which does not comprise a stabilizer
- capsule formulations of Comparative Examples 5 to 8 were prepared by repeating the procedure described in Examples 10 to 13, except that no stabilizer was used.
- the stabilizer of the present invention can improve the stability of silodosin by inhibiting the reaction of silodosin with various excipients.
- dissolution test of the capsule formulations of Examples 10 to 13 comprising various excipients was carried out at 50 rpm in 900 mL of 0.1N HCl solution by a sinker in USP paddle. The results are shown in Table 8 and Fig. 8. In Fig. 8, the dissolution rate of Example 1 is also illustrated for comparison.
- Comparative Example 9 Preparation of silodosin formulation by a different preparation method A capsule formulation was prepared according to the same composition as
- Example 1 by directly filling the mixture into a capsule without a granulation process.
- Example 6 Dissolution test of silodosin according to the preparation method Using the capsule formulations of Example 1 and Comparative Example 9, which were prepared by different preparation methods, dissolution test was carried out at 50 rpm in 900 mL of 0. IN HC1 solution by a sinker in USP paddle. The results are shown in Table 9 and Fig. 9.
- Example 1 which comprises a granule prepared by a wet granulation process
- Comparative Example 9 which was not granulated. This result indicates that preparation of the granule by a wet granulation process is preferable in terms of dissolution rate.
- Example 1 which comprises a granule prepared by a wet granulation process, was shown to have at least about twofold higher C max and AUC as compared to the capsule of Comparative Example 9, which was not granulated. Therefore, it has been determined that a wet granulation process of silodosin results in improved stability, and increased bioavailability of the drug by maximizing the drug concentration in a particular organ, thereby increasing the therapeutic effect of the drug.
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Applications Claiming Priority (2)
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KR10-2014-0040182 | 2014-04-03 | ||
KR1020140040182A KR102206104B1 (ko) | 2014-04-03 | 2014-04-03 | 실로도신을 포함하는 과립물, 및 이를 포함하는 약학적 조성물 및 제형 |
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WO2015152680A1 true WO2015152680A1 (en) | 2015-10-08 |
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PCT/KR2015/003376 WO2015152680A1 (en) | 2014-04-03 | 2015-04-03 | Granule comprising silodosin, and pharmaceutical composition and formulation comprising same |
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WO (1) | WO2015152680A1 (ko) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2018065752A (ja) * | 2016-10-17 | 2018-04-26 | 東和薬品株式会社 | シロドシン含有医薬組成物とその製造方法 |
EP3354283A2 (en) | 2017-06-20 | 2018-08-01 | Alfred E. Tiefenbacher (GmbH & Co. KG) | Pharmaceutical capsule composition comprising silodosin |
JP2018123115A (ja) * | 2017-01-27 | 2018-08-09 | ニプロ株式会社 | 経口固形製剤 |
Citations (5)
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US20030166705A1 (en) * | 2000-05-15 | 2003-09-04 | Hiroo Nitta | Water-based liquid preparation |
WO2012000926A1 (de) * | 2010-06-28 | 2012-01-05 | Ratiopharm Gmbh | Silodosin-cyclodextrin einschlussverbindungen |
WO2012010669A2 (de) * | 2010-07-23 | 2012-01-26 | Ratiopharm Gmbh | Arzneimittel zur oralen verabreichung umfassend ein gemisch aus silodosin und einem basischen copolymer |
US20120064154A1 (en) * | 2002-12-16 | 2012-03-15 | Kissei Pharmaceutical Co., Ltd. | Solid drug for oral use |
WO2014006635A2 (en) * | 2012-07-02 | 2014-01-09 | Hetero Research Foundation | Solid oral compositions of silodosin |
-
2014
- 2014-04-03 KR KR1020140040182A patent/KR102206104B1/ko active IP Right Grant
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2015
- 2015-04-03 WO PCT/KR2015/003376 patent/WO2015152680A1/en active Application Filing
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20030166705A1 (en) * | 2000-05-15 | 2003-09-04 | Hiroo Nitta | Water-based liquid preparation |
US20120064154A1 (en) * | 2002-12-16 | 2012-03-15 | Kissei Pharmaceutical Co., Ltd. | Solid drug for oral use |
WO2012000926A1 (de) * | 2010-06-28 | 2012-01-05 | Ratiopharm Gmbh | Silodosin-cyclodextrin einschlussverbindungen |
WO2012010669A2 (de) * | 2010-07-23 | 2012-01-26 | Ratiopharm Gmbh | Arzneimittel zur oralen verabreichung umfassend ein gemisch aus silodosin und einem basischen copolymer |
WO2014006635A2 (en) * | 2012-07-02 | 2014-01-09 | Hetero Research Foundation | Solid oral compositions of silodosin |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2018065752A (ja) * | 2016-10-17 | 2018-04-26 | 東和薬品株式会社 | シロドシン含有医薬組成物とその製造方法 |
JP7023600B2 (ja) | 2016-10-17 | 2022-02-22 | 東和薬品株式会社 | シロドシン含有医薬組成物とその製造方法 |
JP2018123115A (ja) * | 2017-01-27 | 2018-08-09 | ニプロ株式会社 | 経口固形製剤 |
EP3354283A2 (en) | 2017-06-20 | 2018-08-01 | Alfred E. Tiefenbacher (GmbH & Co. KG) | Pharmaceutical capsule composition comprising silodosin |
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Publication number | Publication date |
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KR102206104B1 (ko) | 2021-01-22 |
KR20150115334A (ko) | 2015-10-14 |
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