WO2015170237A1 - Composition de solifénacine stable - Google Patents
Composition de solifénacine stable Download PDFInfo
- Publication number
- WO2015170237A1 WO2015170237A1 PCT/IB2015/053239 IB2015053239W WO2015170237A1 WO 2015170237 A1 WO2015170237 A1 WO 2015170237A1 IB 2015053239 W IB2015053239 W IB 2015053239W WO 2015170237 A1 WO2015170237 A1 WO 2015170237A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- solifenacin
- pharmaceutical composition
- acid
- composition
- tartaric acid
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
-
- 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
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
-
- 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
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- 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
- A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
- A61K9/2077—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets
Definitions
- the present invention provides a stable solid oral pharmaceutical composition
- a stable solid oral pharmaceutical composition comprising solifenacin and a stabilizer selected from tartaric acid, fumaric acid, maleic acid & succinic acid; wherein solifenacin is in a substantially amorphous form and a process for the preparation of said pharmaceutical composition.
- Solifenacin succinate is a muscarinic receptor antagonist.
- Solifenacin succinate has a chemical name butanedioic acid, compound with 1 (S)-3(R)-1- azabicyclo[2.2.2]oct- 3-yl 3,4-dihydro-l -phenyl-2(l H)-isoquinolinecarboxylate (1 : 1) having an empirical formula C23H26N2O2.C4H6O4 and a molecular weight of 480.55.,
- the structural formula for solifenacin succinate is Formula 1.
- Solifenacin succinate is a white to pale-yellowish-white crystal or crystalline powder. It is freely soluble at room temperature in water, glacial acetic acid, dimethyl sulfoxide, and methanol.
- Solifenacin succinate is available in the market from Astellas Pharmaceuticals Inc. under the name VESICARE ® , in two strengths, 5 mg and 10 mg of solifenacin succinate, and formulated as tablets for oral administration.
- each VESICARE tablet also contains the following inactive excipients: lactose monohydrate, corn starch, hypromellose 2910, magnesium stearate, talc, polyethylene glycol 8000 and titanium dioxide with yellow ferric oxide (5 mg) or red ferric oxide (10 mg). Solifenacin succinate is approved for the treatment of overactive bladder with symptoms of urge urinary incontinence, urgency and urinary frequency.
- EP2500013 discloses a stable pharmaceutical composition comprising crystalline solifenacin and excipient granules wherein excipient granules do not contain solifenacin.
- EP2778167 discloses a pharmaceutical composition that has improved storage stability with respect to dissolution comprising at least 2% w/w disintegrant(s) and solifenacin or pharmaceutical acceptable salt thereof which is substantially free of crystalline form and is free of degradation impurities, characterized in that the composition is prepared by wet granulation. Further it discloses a stable formulation comprising amorphous solifenacin succinate free of stabilizers and antioxidants.
- WO2008128028 discloses a stable composition containing the amorphous form of solifenacin, and a process of manufacturing the composition, wherein solifenacin is stabilized using anti oxidant and polymeric substance.
- US20100273825 discloses a solid pharmaceutical composition
- a solid pharmaceutical composition comprising an amorphous form of solifenacin and a stabilizer selected from the group consisting of citric acid or a pharmaceutically acceptable salt (excluding a calcium salt) thereof, sodium pyrosulfite, and a pharmaceutically acceptable salt of ethylenediaminetetraacetic acid.
- WO2009012987 discloses a pharmaceutical composition
- a pharmaceutical composition comprising solifenacin and a stabilizer selected from HPMC, Lactose, mannitol and the ratio of stabilzer to solifenacin thereof based on parts per weight is at least about 2: 1
- WO2006070735 discloses a stable particulate pharmaceutical composition, comprising solifenacin and a binder having an action of stabilizing solifenacin or a salt thereof.
- solifenacin in the formulation and more particularly in an amorphous form.
- Various techniques are tried in the prior art to stabilize amorphous solifenacin.
- Fig 1 illustrates an overlay of the XRPD pattern of solifenacin succinate, placebo and tablet of Ex.9.
- One object of the present invention provides a stable solid oral pharmaceutical composition
- a stable solid oral pharmaceutical composition comprising solifenacin and a stabilizer selected from tartaric acid, fumaric acid, maleic acid & succinic acid; wherein solifenacin is in a substantially amorphous form.
- present invention provides a stable pharmaceutical composition
- a stable pharmaceutical composition comprising solifenacin having less than 0.1% of N-oxide impurity during shelf life, preferably 0.06%, more Preferably solifenacin N-oxide impurity is 0.03%. Most preferably solifenacin N-oxide impurity is 0.01% under normal storage condition.
- One object of the present invention is to provide a stable solid oral pharmaceutical composition comprising solifenacin, prepared by a process comprising steps of:
- step (b) granulating the mixture comprising solifenacin , water soluble polymer & optionally other pharmaceutical excipient with solution prepared in step (a);
- step (c) optionally, drying the granules prepared in step (b);
- step (d) mixing granules prepared in step (b) or (c) optionally with diluent and lubricant;
- Another object of present invention is to provide a process for the preparation of a stable solid oral pharmaceutical composition comprising steps of:
- step a) granulating the mixture comprising solifenacin, water soluble polymer and one or more diluent with solution prepared in step a);
- step (c) optionally, drying the granules prepared in step (b);
- step (d) mixing granules prepared in step (b) or (c) optionally with diluent and lubricant;
- the present invention provides a stable pharmaceutical composition
- a stabilizer selected from tartaric acid, fumaric acid, maleic acid & succinic acid and a process for the preparation of said pharmaceutical composition.
- the present invention also provides a stable pharmaceutical composition
- a stable pharmaceutical composition comprising solifenacin and a stabilizer selected from tartaric acid, fumaric acid, maleic acid & succinic acid, wherein solifenacin is in a substantially amorphous form.
- the present invention also provides a stable pharmaceutical composition
- a stable pharmaceutical composition comprising solifenacin having less than 0.1% of N-oxide impurity during shelf life, preferably 0.06%, more Preferably solifenacin N-oxide impurity is 0.03%. Most preferably solifenacin N-oxide impurity is 0.01% under normal storage condition.
- amorphous or “amorphous form” refers that recognizable characteristic crystalline solifenacin peaks are not present in an X-ray powder diffraction.
- substantially amorphous refers that pharmaceutical composition of the present invention comprises at least about 90 wt % of solifenacin is in an amorphous form, yet more preferably at least about 95 wt % and even more preferably at least about 99 wt % of solifenacin is in an amorphous form. In a most preferred embodiment, all or substantially all of the solifenacin is in an amorphous form.
- under normal storage conditions refers that the storage conditions at 40°C and 75% RH for minimum period of one month and/or till normal shelf life i. e 24-36 months.
- solifenacin refers that it is pharmaceutically acceptable and helps to stabilize an amorphous form of solifenacin.
- a and “an” and “the” and similar referents in the context of describing the invention are to be construed to cover both the singular and the plural, unless otherwise indicated herein or clearly contradicted by context.
- the words “comprise”, “have”, “contain” and “include” and variations such as “comprises”, “comprising”, “having”, “containing” “includes”, “including” are to be interpreted inclusively, unless the context requires otherwise.
- solifenacin as used herein includes solifenacin or its isomers, its enantiomers, its racemates, its pharmaceutically acceptable salts or its polymorphs, or mixtures thereof.
- "solifenacin” present in the composition according to present invention is solifenacin succinate.
- First embodiment of the invention provides a stable pharmaceutical composition comprising solifenacin prepared by a process comprising steps of:
- step (a) preparing a solution comprising a stabilizer selected from tartaric acid, maleic acid, fumaric acid & succinic acid , an antioxidant and solvent; (b) granulating the mixture comprising solifenacin, water soluble polymer & optionally other pharmaceutical excipient with solution prepared in step (a);
- step (c) optionally, drying the granules prepared in step (b);
- step (d) mixing granules prepared in step (b) or (c) with optionally diluent and lubricant;
- step (e) preparing a pharmaceutical composition from the mixture or blend of step (d).
- Solution of step (a) comprising a stabilizer selected from tartaric acid, maleic acid, fumaric acid & succinic acid in purified water and an antioxidant in ethanol prepared by adding components in any order, preferably, solution of antioxidant in ethanol is prepared first and then stabilizer is dissolved in purified water.
- a preferred embodiment of the invention provides a stable solid oral pharmaceutical composition
- a stable solid oral pharmaceutical composition comprising granulation of the mixture comprising solifenacin, water soluble polymer such as hydroxypropyl methyl cellulose or polyvinyl pyrrolidone, disintegrant such as pregelatinized starch and one or more diluent such as lactose monohydrate, microcrystalline cellulose by a granulating solution comprising stabilizer such as tartaric acid, succinic acid, maleic acid and fumaric acid, antioxidant such as butylated hydroxy toluene in Solvent.
- Another embodiment of present invention provides a stable solid oral pharmaceutical composition comprising of solifenacin, stabilizer, antioxidant, binder, disintegrant and lubricant.
- Another embodiment of the invention provides, a stable solid oral pharmaceutical composition
- a stable solid oral pharmaceutical composition comprising solifenacin; antioxidants selected from sodium hydrogen sulfite, tocopherol acetate, tocopherol, propyl gallate, Butyl hydroxy toluene, Butyl hydroxy anisole and stabilizers selected from tartaric acid, fumaric acid, succinic acid and maleic acid; wherein solifenacin is in a substantially amorphous form.
- Yet another embodiment of the invention provides, a stable solid oral pharmaceutical composition
- a stable solid oral pharmaceutical composition comprising solifenacin; Butyl hydroxy toluene and stabilizer selected from tartaric acid, fumaric acid, succinic acid and maleic acid; wherein solifenacin is in a substantially amorphous form.
- a most preferred embodiment of the invention provides, a stable solid oral pharmaceutical composition comprising solifenacin; Butyl hydroxy toluene and tartaric acid, wherein solifenacin is in a substantially amorphous form.
- a preferred embodiment of the invention provides a stable solid oral pharmaceutical composition comprising of 5% to 12% w/w of solifenacin, 0.01% to 4% w/w of stabilizer, 0.01% to 4 % w/w of antioxidant, 0.01% to 5% w/w of binder, 1% to 25% w/w of disintegrant & 0.1% to 5% w/w of lubricant of total weight of the composition.
- Another embodiment of the invention provides a stable solid oral pharmaceutical composition
- a stable solid oral pharmaceutical composition comprising of 6.47% w/w of solifenacin, 3.24 % w/w of stabilizer selected from tartaric acid, succinic acid, maleic acid and fumaric acid, 0.26 % w/w of butylated hydroxy toluene, 2.59% w/w of hydroxypropyl methyl cellulose or polyvinyl pyrrolidone, 16.18% w/w of pregelatinized starch and 1.17 % w/w of magnesium stearate of total weight of the composition.
- a preferred embodiment of the invention provides a stable solid oral pharmaceutical composition consisting of 6.47% w/w of solifenacin, 3.24 % w/w of tartaric acid, 0.26 % w/w of butylated hydroxytoluene, 2.59% w/w of hydroxypropyl methyl cellulose, 16.18% w/w of pregelatinized starch and 1.17 % w/w of magnesium stearate of total weight of the composition.
- a stable solid oral pharmaceutical composition consisting of 6.47% w/w of solifenacin, 3.24 % w/w of tartaric acid, 0.26 % w/w of butylated hydroxytoluene, 1.29 % w/w of hydroxypropyl methyl cellulose, 8.09 % w/w of pregelatinized starch and 0.58 % w/w of magnesium stearate of total weight of the composition.
- Another embodiment of present invention provides a process for the preparation of a stable solid oral pharmaceutical composition of solifenacin comprising steps of: (a) preparing a solution comprising butylated hydroxy toluene in ethanol & tartaric acid in purified water;
- step a) granulating the mixture comprising solifenacin, hydroxypropyl methyl cellulose pregelatinized starch, lactose monohydrate, with solution prepared in step a);
- step (c) optionally, drying the granules prepared in step (b);
- step (d) mixing granules prepared in step (b) or (c) with lactose monohydrate and magnesium stearate;
- step (e) preparing a pharmaceutical composition from the mixture or blend of step (d).
- composition of present invention were found stable with less than 0.1% of N-oxide impurity, even when packed in standard packaging material including blister or bottle packs; wherein special treatment for oxygen or moisture protection such as oxygen scavenger, desiccant or nitrogen flushing are not required.
- composition is packed in a container selected from blister pack or bottle pack.
- Blister pack is preferably selected from Alu-Alu, polyvinyl chloride and polystyrene.
- Bottle pack is preferably selected from high density polyethylene (HDPE), low density polyethylene (LDPE) and polyethylene terephthalate (PET).
- Pharmaceutical excipient according to present invention may comprise diluent, disintegrant, lubricant, antioxidant, stabilizer and the like.
- compositions according to present invention may optionally further comprises one or more glidant, binder, surfactant, flavoring agent, preservatives, and the like.
- glidant e.g., abrasin, aluminosilicate, aluminosilicate, aluminosilicate, aluminosilicate, aluminosilicate, aluminosilicate, aluminosilicate, sulfate, sulfate, sulfate, sulfate, sulfate, stylitol, nitrate, glycerin, glycerin, adiol, glycerin, aric acid, sulfate, arate, glycerin, arate, arate, glycerin, arate, arate, glycerin, arate, glycerin, glycerin, arate, glycer
- a diluent according to present invention includes powdered cellulose, microcrystalline cellulose, silicified microcrystalline cellulose, starch, dibasic calcium phosphate, dibasic sodium phosphate, tribasic sodium phosphate; sugars such as dextrose, lactose, lactose monohydrate or sucrose; sugar alcohols such as mannitol, sorbitol, xylitol or erythritol; or mixtures thereof; most preferably diluent is lactose mono hydrate & microcrystalline cellulose.
- Pharmaceutical composition comprises diluent in the amount of 50-95% w/w of the total composition.
- a disintegrant according to present invention includes calcium carboxymethyl cellulose and its salt including sodium or calcium salt, cross-linked carboxymethyl cellulose sodium, cross-linked carboxymethyl cellulose calcium, cross-linked polyvinyl pyrrolidone, sodium starch glycolate, pregelatinized starch, low substituted hydroxypropyl cellulose; or mixtures thereof, more preferably disintegrant is pregelatinized starch
- Pharmaceutical composition comprises disintegrant in the amount of 1 - 25% w/w of the total composition.
- a binder according to present invention includes polyvinyl alcohol, starch, pregelatinised starch; cellulose derivatives such as cellulose powder, microcrystalline cellulose, hydroxypropyl methylcellulose, ethyl cellulose, methyl cellulose, hydroxypropyl cellulose, hydroxyethyl cellulose, gelatin, zein, polymethacrylates, sodium alginate, gums, synthetic resins or mixtures thereof; more preferably binder is hydroxypropylmethyl cellulose.
- Pharmaceutical composition comprises binder in the amount of 0.01-5% w/w of the total composition.
- a lubricant according to present invention includes talc, metallic stearate such as magnesium stearate, calcium stearate, zinc stearate; colloidal silicon dioxide, finely divided silicon dioxide, stearic acid, hydrogenated vegetable oil, glyceryl palmitostearate, glyceryl monostearate, glyceryl behenate, sodium stearyl fumarate, magnesium trisilicate or mixtures thereof; more preferably lubricant is magnesium stearate.
- Pharmaceutical composition comprises lubricant in the amount of 0.1-5% w/w of the total composition.
- An antioxidant according to present invention includes sodium hydrogen sulfite, tocopherol acetate, tocopherol, propyl gallate, Butyl hydroxy toluene, Butyl hydroxy anisole; more preferably antioxidant is Butyl hydroxy toluene.
- Pharmaceutical composition comprises antioxidant in the amount of 0.01- 4% w/w of the total composition.
- a stabilizer according to present invention includes tartaric acid, maleic acid, fumaric acid, succinic acid and the like or mixture thereof, preferably tartaric acid, maleic acid, fumaric acid, most preferably tartaric acid.
- Pharmaceutical composition comprises stabilizer in the amount of 0.01- 4 % w/w of the total composition.
- a water soluble polymer according to present invention includes hydroxypropylmethylcellulose, polyvinylpyrrolidone, methylcellulose and the like.
- Pharmaceutical composition comprises water soluble polymer in the amount of 0.1- 5 % w/w of the total composition. Water soluble polymers as defined herein can also act as a binder in the present composition.
- a Suitable solvent according to present invention includes organic, aqueous, or a mixture thereof.
- Organic solvents may be aliphatic alcohols such as methanol, ethanol, n-propanol, and isopropanol; aliphatic ketones such as acetone and methyl ethyl ketone; aliphatic carboxylic esters such as ethyl acetate; aromatic hydrocarbons such as toluene and xylene; aliphatic hydrocarbons such as hexane; aliphatic nitriles such as acetonitrile; chlorinated hydrocarbons such as dichloromethane; aliphatic sulfoxides such as dimethyl sulfoxide; and the like, as well as mixtures comprising at least one of the foregoing organic solvents.
- Aqueous solvents include solvent comprising water, water and/or a water-miscible organic solvent such as a lower alcohol, acetonitrile, tetrahydrofuran, dimethylacetamide, dimethyl formamide, and the like. Combination of various solvents can also be used. Most preferable is water & ethanol.
- a pharmaceutical composition according to present invention may optionally comprise a coating.
- Coating according to present invention may be functional or non-functional coating, preferably coating is non-functional coating.
- Non-functional coating comprises a film forming polymer and one or more excipients suitable for said coating.
- a coating can be applied using the materials and methods known to a person skilled in the art.
- film coating material includes Opadry® which is Colorcon's customized, one-step film coating system which combines polymer, plasticizer, opacifier, and pigment, as required, in a dry concentrate.
- a pharmaceutical composition according to present invention is a solid composition for immediate release for oral administration and it can be in the form of tablet or capsule. Preferably, said composition is in the form of tablet for oral administration.
- step (c) Both solutions prepared in step (b) were added in the dry mixture prepared in step (a) to obtain granules;
- step (d) The granules prepared in step (c) were dried in fluidized bed dryer.
- step (e) The granules prepared in step (d) were mixed with lactose monohydrate and magnesium stearate.
- step (f) The above mixture prepared in step (e) was compressed to obtain tablet;
- step (d) The granules prepared in step (c) were dried in fluidized bed dryer.
- step (e) The granules prepared in step (d) were mixed with lactose monohydrate and magnesium stearate.
- step (f) The above mixture prepared in step (e) was compressed to obtain tablet;
- compositions of Example 5 to 7 were kept for forced degradation studies for 48 hours under the conditions of heat and moisture at 80°C. Forced degradation data of composition are summarized in table 1.
- N-oxide impurity of solifenacin was carried out using gradient- reverse phase HPLC with UV detection.
- the method for determining the amount of N-oxide impurity in a solifenacin succinate tablet comprises the steps of:
- the Relative retention time of N-oxide impurity is about 1.09
- compositions of present invention provided excellent stability for controlling N-oxide impurity in formulation.
- Example 5 Composition of Example 5 was kept for stability testing for 1 month under the conditions 40°C/75% RH. Stability data of composition are summarized in table 2.
- step (c) Both solutions prepared in step (b) added in the dry mixture prepared in step (a) to obtain granules; (d) The granules prepared in step (c) were dried in fluidized bed dryer.
- step (e) The granules prepared in step (d) were mixed with lactose monohydrate and magnesium stearate.
- step (f) The above mixture prepared in step (e) was compressed to obtain tablet;
- compositions of Examples 9 were packed in Alu-Alu blister and HDPE bottle for 6 month at 40°C/75% RH to determine impact of stabilizer to control the impurity (N- oxide) on the stability of the product. Results are summarized in Table 3.
- compositions of present invention provided excellent stability for controlling N-oxide impurity on stability in the composition.
- composition of present invention has been found more stable in comparison to marketed solifenacin compositions as herein described below:
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Abstract
La présente invention concerne une composition pharmaceutique orale solide stable qui comprend de la solifénacine et un stabilisant sélectionné dans le groupe comprenant acide tartrique, acide fumarique, acide maléique et acide succinique ; la solifénacine se présentant sous une forme sensiblement amorphe.
Applications Claiming Priority (2)
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IN1555/MUM/2014 | 2014-05-05 | ||
IN1555MU2014 | 2014-05-05 |
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WO2015170237A1 true WO2015170237A1 (fr) | 2015-11-12 |
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Cited By (8)
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WO2017082577A1 (fr) * | 2015-11-11 | 2017-05-18 | 한미약품 주식회사 | Préparation solide contenant de la solifénacine amorphe à usage oral et son procédé de préparation |
JP2017210422A (ja) * | 2016-05-24 | 2017-11-30 | ニプロ株式会社 | 医薬組成物、医薬組成物の製造方法、及び非晶質体の安定性を向上させる方法 |
JP2018039780A (ja) * | 2016-09-02 | 2018-03-15 | 大原薬品工業株式会社 | 非晶質体ソリフェナシン及び抗酸化剤を含有する固形製剤 |
JP2018100271A (ja) * | 2016-12-21 | 2018-06-28 | ニプロ株式会社 | 固形製剤及び非晶質体の安定性を向上させる方法 |
JP2018177789A (ja) * | 2017-04-14 | 2018-11-15 | 東和薬品株式会社 | コハク酸ソリフェナシン含有固形医薬組成物 |
JP2020203955A (ja) * | 2020-09-30 | 2020-12-24 | ニプロ株式会社 | 医薬組成物、医薬組成物の製造方法、及び非晶質体の安定性を向上させる方法 |
CN113440492A (zh) * | 2020-03-27 | 2021-09-28 | 广东东阳光药业有限公司 | 一种毒蕈碱受体拮抗剂的组合物及其制备方法 |
WO2022072811A1 (fr) * | 2020-10-01 | 2022-04-07 | Imago Biosciences, Inc. | Formulations pharmaceutiques pour le traitement de maladies médiées par kdm1a |
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Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2017082577A1 (fr) * | 2015-11-11 | 2017-05-18 | 한미약품 주식회사 | Préparation solide contenant de la solifénacine amorphe à usage oral et son procédé de préparation |
JP2017210422A (ja) * | 2016-05-24 | 2017-11-30 | ニプロ株式会社 | 医薬組成物、医薬組成物の製造方法、及び非晶質体の安定性を向上させる方法 |
JP2018039780A (ja) * | 2016-09-02 | 2018-03-15 | 大原薬品工業株式会社 | 非晶質体ソリフェナシン及び抗酸化剤を含有する固形製剤 |
JP2018100271A (ja) * | 2016-12-21 | 2018-06-28 | ニプロ株式会社 | 固形製剤及び非晶質体の安定性を向上させる方法 |
JP7098925B2 (ja) | 2016-12-21 | 2022-07-12 | ニプロ株式会社 | 固形製剤及び非晶質体の安定性を向上させる方法 |
JP2018177789A (ja) * | 2017-04-14 | 2018-11-15 | 東和薬品株式会社 | コハク酸ソリフェナシン含有固形医薬組成物 |
JP7102200B2 (ja) | 2017-04-14 | 2022-07-19 | 東和薬品株式会社 | コハク酸ソリフェナシン含有固形医薬組成物 |
CN113440492A (zh) * | 2020-03-27 | 2021-09-28 | 广东东阳光药业有限公司 | 一种毒蕈碱受体拮抗剂的组合物及其制备方法 |
JP2020203955A (ja) * | 2020-09-30 | 2020-12-24 | ニプロ株式会社 | 医薬組成物、医薬組成物の製造方法、及び非晶質体の安定性を向上させる方法 |
WO2022072811A1 (fr) * | 2020-10-01 | 2022-04-07 | Imago Biosciences, Inc. | Formulations pharmaceutiques pour le traitement de maladies médiées par kdm1a |
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