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
  • A61K31/222—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin with compounds having aromatic groups, e.g. dipivefrine, ibopamine
• • 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
  • A61K47/02—Inorganic compounds
• • 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
  • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
  • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
  • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
• • 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
  • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
  • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
  • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
  • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
  • A61K47/38—Cellulose; Derivatives thereof
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K9/00—Medicinal preparations characterised by special physical form
  • A61K9/20—Pills, tablets, discs, rods
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P13/00—Drugs for disorders of the urinary system
  • A61P13/10—Drugs for disorders of the urinary system of the bladder

Definitions

• One embodiment of the present invention relates to a method for producing a fesoterodine fumarate-containing preparation.
• Hydrogen fumarate of 2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)phenyl isobutyrate (hereinafter referred to as fesoterodine fumarate) is It is a therapeutic agent for active bladder. Fesoterodine fumarate is known to degrade under harsh environmental conditions such as high humidity or high temperature. (Patent document 1).
• Patent Document 1 discloses a pharmaceutical composition containing fesoterodine fumarate and specific polyols as a stabilizer, and a wet granulation method as a method for producing the same, which exhibits excellent stability. is described.
• the wet granulation method requires a step of adding water such as preparation of a binding liquid in the pre-granulation process, and a step of drying the granules after granulation.
• the manufacturing process is more complicated and the manufacturing cost is higher.
• polyol-based stabilizers such as xylitol and sorbitol used in Patent Document 1 are not cheap, and since xylitol exhibits deliquescence, it must be handled with care. For these reasons, there is a demand for the development of a pharmaceutical composition containing fesoterodine fumarate that exhibits excellent stability and can be produced by a simpler production method.
• An object of one embodiment of the present invention is to provide a method for producing a stable fesoterodine fumarate-containing preparation that suppresses the production of related substances by using an easy-to-handle general-purpose additive and a simple production method.
• fesoterodine fumarate, lactose, microcrystalline cellulose and lubricant are dry granulated to obtain a granule.
• Methods of making salt-containing formulations are provided.
• the granules may contain sucrose fatty acid ester or glycerin fatty acid ester as a lubricant.
• the obtained granules, lactose, crystalline cellulose, hypromellose, and a lubricant may be mixed and tableted.
• a glycerin fatty acid ester may be included as a lubricant mixed with the granules.
• Talc may be further included as a lubricant mixed with the granules.
• fesoterodine fumarate comprising mixing fesoterodine fumarate, lactose, microcrystalline cellulose, hypromellose and a lubricant and compressing, comprising fesoterodine fumarate , lactose, microcrystalline cellulose, hypromellose, and a lubricant are each mixed as dry powders to produce a fesoterodine fumarate-containing preparation.
• Talc and glycerin fatty acid esters may be included as lubricants.
• a method for producing a stable fesoterodine fumarate-containing preparation that suppresses the production of related substances, using an easy-to-handle general-purpose additive and a simple production method.
• a method for producing a fesoterodine fumarate-containing preparation according to the present invention will be described below.
• the manufacturing method of the fesoterodine fumarate-containing preparation of the present invention should not be construed as being limited to the contents described in the following embodiments and examples.
• xylitol is used as a stabilizer, and xylitol is known to be a deliquescent additive. Therefore, the present inventors investigated the stability of fesoterodine fumarate-containing preparations produced by the wet granulation method described in Patent Document 1 using other non-deliquescent sugar alcohols. . As a result, a marked increase in related substances was observed. Therefore, xylitol was shown to be an essential constituent component as a stabilizer in the formulation containing fesoterodine fumarate described in Patent Document 1, which employs a wet granulation method.
• Table 8 of Patent Document 1 describes the stability results of tablets produced by a direct compression method in the presence of xylitol
• Table 9 shows the stability of tablets produced by a dry granulation method. Results are given. However, both methods have been shown to produce more hydrolyzate and total degradation products than tablets produced by wet granulation.
• Patent Document 1 it is difficult to obtain a stable fesoterodine fumarate-containing preparation by a production method using a direct compression method or a dry granulation method, which are simpler production methods. was suggested.
• the inventors have found that applying dry granulation or direct compression to specific formulations with easy-to-handle common excipients yields stable fesoterodine fumarate-containing formulations. I found Compared to the wet granulation method, the dry granulation method or direct compression method has fewer manufacturing steps and can be manufactured at low cost, so the dry granulation method or direct compression method is easier to manufacture. method.
• fesoterodine fumarate, lactose, crystalline cellulose, and a lubricant are dry granulated, and granulated. Including obtaining granules.
• Granules can be produced using a roller compactor.
• the lactose used in the present embodiment may be an anhydride or a hydrate.
• the fesoterodine fumarate-containing formulation can contain, but is not limited to, 4 mg or 8 mg of fesoterodine fumarate per tablet.
• the content of fesoterodine fumarate can be varied within the range where a therapeutic effect can be obtained.
• the content of lactose contained in the granules may be in the range of 55% by mass to 85% by mass with respect to 100% by mass of the granules.
• the content of crystalline cellulose contained in the granules may be in the range of 5% by mass to 35% by mass with respect to 100% by mass of the granules.
• a sucrose fatty acid ester or a glycerin fatty acid ester can be selected as a lubricant added during dry granulation. That is, the obtained granules can contain sucrose fatty acid ester or glycerin fatty acid ester as a lubricant. In this embodiment, the sucrose fatty acid ester and the glycerin fatty acid ester have little effect on the amount of hydrolyzate and the total amount of related substances in the fesoterodine fumarate-containing preparation. In one embodiment, the content of the lubricant contained in the granules may be in the range of 0.6% by mass to 2.5% by mass with respect to 100% by mass of the granules.
• polyvinyl alcohol can be further added during dry granulation.
• the obtained granules, lactose, crystalline cellulose, hypromellose, and a lubricant are mixed and tableted to produce a fesoterodine fumarate-containing preparation according to the present embodiment.
• the tableting step may be either a dry tableting method or a wet tableting method as long as the granules obtained in the present invention are used.
• the lactose used in the present embodiment may be an anhydride or a hydrate.
• the fesoterodine fumarate-containing preparation according to the present embodiment contains glycerin fatty acid ester as a lubricant mixed with the granules.
• the fesoterodine fumarate-containing formulation may further comprise talc as a lubricant mixed with the granulation.
• high-viscosity HPMC and low-viscosity HPMC can be used in combination as hypromellose (hereinafter also referred to as HPMC) mixed with the granules.
• HPMC hypromellose
• High-viscosity HPMC has a nominal viscosity (measured by an Ubbelohde viscometer) of about 70,000 mPa s to about 150,000 mPa s, preferably about 100,000 mPa at 22° C. in an aqueous solution of about 2% by mass. • s, indicating an HPMC that is 100,000 ⁇ 20,000 mPa ⁇ s.
• high-viscosity HPMC for example, Dow Chemical's METHOCEL (registered trademark) K15M or METHOCEL (registered trademark) K100M can be used.
• low-viscosity HPMC has a nominal viscosity of about 3,000 mPa ⁇ s to about 20,000 mPa ⁇ s, preferably about 4,000 mPa ⁇ s in an aqueous solution of about 2% by mass at 22°C. HPMC is shown to be 4,000 mPa ⁇ s ⁇ 1,000 mPa ⁇ s.
• METHOCEL (registered trademark) E4M or METHOCEL (registered trademark) K4M from Dow Chemical can be used.
• a direct compression method can be used to produce a fesoterodine fumarate-containing formulation that suppresses an increase in the amount of hydrolyzate of fesoterodine fumarate and an increase in the amount of total related substances.
• fesoterodine fumarate, lactose, crystalline cellulose, hypromellose, and a lubricant are mixed, Compression molding (tabletting) is performed using a commonly used tableting machine.
• Compression molding (tabletting) is performed using a commonly used tableting machine.
• fesoterodine fumarate, lactose, microcrystalline cellulose, hypromellose, and lubricant are each mixed as dry powders. That is, no solvents are used in the mixing process.
• the lactose used in the present embodiment may be an anhydride or a hydrate.
• the fesoterodine fumarate-containing formulation can contain, but is not limited to, 4 mg or 8 mg of fesoterodine fumarate per tablet.
• the content of fesoterodine fumarate can be varied within the range where a therapeutic effect can be obtained.
• the lubricant contains talc and glycerin fatty acid ester.
• fesoterodine fumarate-containing preparation can be used in combination with the above-described high-viscosity HPMC and low-viscosity HPMC as hypromellose, detailed description is omitted.
• the fesoterodine fumarate-containing preparation according to this embodiment can also be a film-coated tablet obtained by applying a film coating to an uncoated tablet obtained by a dry granulation method or a direct compression method.
• a general-purpose film composition can be applied as the film to be coated on the fesoterodine fumarate-containing preparation.
• Polymers, plasticizers, colorants, opacifiers, and/or fillers may be included in the film composition. It may also contain minor amounts of flavors, surfactants and waxes.
• Polymers included in the film composition can be cellulose derivatives such as cellulose ethers, acrylic polymers, and copolymers. Polyethylene glycol, polyvinylpyrrolidone, polyvinyl alcohol and waxy materials can also be used.
• cellulose ethers additives selected from the group consisting of hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropylmethyl cellulose and methyl cellulose can be used.
• Acrylic polymers can include synthetic polymers with diverse functional groups. Synthetic polymers may be further modified to enhance their swellability. It can also be combined with materials such as water-soluble cellulose ethers and starches.
• Plasticizers include polyols (glycerol, propylene glycol, macrogol), organic esters (phthalates, basic dibutyl acetate, citrates, triacetin), oils/glycerides (castor oil, acetylated monoglycerides). and fractionated coconut oil) can be used.
• colorants/opacifiers organic dyes and their lakes, inorganic colorants, and natural colorants can be used, and each material can be combined in a specified ratio.
• Film-coated tablets can be produced by spraying film compositions onto uncoated tablets as dispersions or suspensions using various solvents (water, alcohols, ketones, esters, chlorinated hydrocarbons). .
• stability is evaluated by quantification of fesoterodine fumarate hydrolyzate and total related substances using liquid chromatography.
• area percentage method the total peak area of each component of fesoterodine fumarate and fesoterodine fumarate-derived analogues obtained on the chromatogram was set to 100, and the ratio of the peak areas was determined as fesoterodine fumarate. Calculate the total amount (%) of related substances derived from acid salts.
• Example 1 As Example 1, a formulation containing fesoterodine fumarate was produced by direct compression. 4 g fesoterodine fumarate, lactose hydrate (75%)/microcrystalline cellulose (25%) (MEGGLE, MICROCELAC® 100M) 74.75 g, hypromellose (Dow Chemical, METHOCEL® K100M) 60 g , Hypromellose (Dow Chemical, METHOCEL (registered trademark) K4M) 12 g, talc (Fuji Talc Co., Ltd.) 4.25 g, glycerin fatty acid ester (Compritol 888ATO, GATTEFOSSE) 5 g were mixed in a plastic bag, and a tableting machine (Kikusui Co., Ltd. The fesoterodine fumarate-containing preparation of Example 1 was obtained by tableting to a weight of 320 mg using Seisakusho Co., Ltd.
• Example 2 As Example 2, a preparation containing fesoterodine fumarate was produced by dry granulation. Fesoterodine fumarate 8g, anhydrous lactose (DFEPharma, SuperTabNA21) 57g, crystalline cellulose (Asahi Kasei Corporation, CEOLUS (registered trademark) PH-102) 13.7g, polyvinyl alcohol (Mitsubishi Chemical Corporation, EG-05PW) 0 8 g and 0.5 g of glycerin fatty acid ester (GATTEFOSSE, Compritol 888ATO) were added and mixed, and then dry granulation was performed using a roller compactor (TF-MINI, Freund Corporation) at a roll pressure of 100 kgf/cm 2 , A dry granule was obtained.
• TF-MINI glycerin fatty acid ester
• Example 2 using a tableting machine (Kikusui Seisakusho Co., Ltd., VELA5), tableting was performed so that the weight was 320 mg, and the fesoterodine fumarate-containing preparation of Example 2 was obtained.
• a tableting machine Kikusui Seisakusho Co., Ltd., VELA5
• Comparative Example 1 As Comparative Example 1, a preparation containing fesoterodine fumarate was produced by a wet granulation method. Fesoterodine fumarate 8g, anhydrous lactose (DFE Pharma, SuperTabNA21) 57g, crystalline cellulose (Asahi Kasei Corporation, CEOLUS (registered trademark) PH-102) 13.7g, polyvinyl alcohol (Mitsubishi Chemical Corporation, EG-05PW) 0.8 g was put into a mortar and mixed. After that, 5 g of purified water was added, and stirring and kneading were performed.
• Reference Example 1 As Reference Example 1, a fesoterodine fumarate-containing preparation containing xylitol was produced by a wet granulation method according to the method described in Patent Document 1. 8 g of fesoterodine fumarate and 72 g of xylitol (Xylitol P, Mitsubishi Shoji Foodtech Co., Ltd.) were put into a mortar and mixed. After that, 5 g of purified water was added, and stirring and kneading were performed.
• lactose hydrate (75%)/microcrystalline cellulose (25%) (MEGGLE, MICROCELAC (registered trademark) 100M) 77.5 g, hypromellose (Dow Chemical, METHOCEL (registered trademark) K100M) 120 g, hypromellose (Dow Chemical, METHOCEL (registered trademark) K4M) 24 g, talc (Fuji Talc Co., Ltd.) 8.5 g, glycerin fatty acid ester (GATTEFOSSE, Compritol 888ATO) 10 g were mixed in a plastic bag.
• GATTEFOSSE Compritol 888ATO
• Comparative Example 2 Fesoterodine fumarate of Comparative Example 2 was produced in the same manner as in Reference Example 1, except that the sugar alcohol was changed from xylitol to D-mannitol (Mitsubishi Shoji Foodtech Co., Ltd., Mannitol P). A formulation was obtained.
• Comparative Example 3 A fesoterodine fumarate-containing preparation of Comparative Example 3 was obtained in the same manner as the production method of Reference Example 1, except that the sugar alcohol was changed from xylitol to erythritol (Erythritol 100M, Bussan Food Science Co., Ltd.). .
• Example 1 the left value in each column indicates the amount of hydrolyzate, and the right value indicates the total amount of related substances. From the results in Table 1, the fesoterodine fumarate-containing preparation of Example 1 produced using the direct compression method and the fesoterodine fumarate-containing preparation of Example 2 produced using the dry granulation method were: It was found that the fesoterodine fumarate-containing preparation of Reference Example 1 exhibits the same stability.
• the fesoterodine fumarate-containing preparation of Comparative Example 2 produced by wet granulation with D-mannitol instead of xylitol and the fesoterodine fumarate-containing preparation of Comparative Example 3 produced by wet granulation with erythritol in place of xylitol
• the fesoterodine fumarate-containing preparation of Comparative Example 1 produced by wet granulation showed a significant increase in the amount of hydrolyzate and the total amount of related substances.
• Example 3 As Example 3, 74.75 g of lactose hydrate (75%) / crystalline cellulose (25%) (MEGGLE, MICROCELAC (registered trademark) 100M), 54.25 g of anhydrous lactose (DFEPharma, SuperTabNA21), crystalline cellulose (Asahi Kasei Co., Ltd. CEOLUS (registered trademark) PH-102) was changed to 22.5 g, and hypromellose (Dow Chemical, METHOCEL (registered trademark) K4M) was changed to 10 g. Thus, the fesoterodine fumarate-containing formulation of Example 3 was obtained.
• METHOCEL registered trademark
• Example 4 As Example 4, fesoterodine fumarate 8 g, lactose hydrate (Pharmatose 200M, DMV) 45 g, crystalline cellulose (Asahi Kasei Corporation, CEOLUS (registered trademark) PH-102) 25 g, glycerin fatty acid ester (GATTEFOSSE, Compritol 888ATO) After adding and mixing 2.0 g, dry granulation was performed using a roller compactor (TF-MINI, Freund Corporation) at a roll pressure of 100 kgf/cm 2 to obtain dry granules.
• TF-MINI roller compactor
• a fesoterodine fumarate-containing preparation of Example 4 was obtained by the same production method as in Example 2 using the obtained granules.
• Example 5 As Example 5, 8 g of fesoterodine fumarate, 45 g of anhydrous lactose (DFEPharma, SuperTab NA21), 25 g of crystalline cellulose (CEOLUS (registered trademark) PH-102, Asahi Kasei Corporation), glycerin fatty acid ester (GATTEFOSSE, Compritol888ATO)2. After adding 0 g and mixing, dry granulation was performed using a roller compactor (TF-MINI, Freund Corporation) at a roll pressure of 100 kgf/cm 2 to obtain dry granules.
• TF-MINI roller compactor
• Example 6 A fesoterodine fumarate-containing preparation of Example 6 was obtained in the same manner as the production method of Example 2, except that the anhydrous lactose was changed to 66.7 g and the crystalline cellulose was changed to 4 g.
• Example 7 A preparation containing fesoterodine fumarate of Example 7 was obtained in the same manner as in Example 2, except that polyvinyl alcohol was not added and anhydrous lactose was changed to 57.8 g.
• Example 8 Fesoterodine fumarate of Example 8 was prepared in the same manner as in Example 2, except that polyvinyl alcohol was not added, anhydrous lactose was changed to 46.5 g, and crystalline cellulose was changed to 25 g. A containing formulation was obtained.
• Example 9 Fesoterodine of Example 9 was prepared in the same manner as in Example 2, except that polyvinyl alcohol was not added, anhydrous lactose was changed to 57.3 g, and glycerin fatty acid ester was changed to 1.0 g. A fumarate-containing formulation was obtained.
• Example 10 Fesoterodine of Example 10 was prepared in the same manner as in Example 2, except that polyvinyl alcohol was not added, anhydrous lactose was changed to 56.3 g, and glycerin fatty acid ester was changed to 2.0 g. A fumarate-containing formulation was obtained.
• Example 11 Except that polyvinyl alcohol was not added, the anhydrous lactose was changed to 45 g, the crystalline cellulose was changed to 25 g, and the glycerin fatty acid ester was changed to 2.0 g. A fesoterodine fumarate-containing formulation of Example 11 was obtained.
• Example 12 A fesoterodine fumarate-containing preparation of Example 12 was obtained in the same manner as the production method of Example 2, except that glycerin fatty acid ester was changed to sucrose fatty acid ester.
• the left value in each column indicates the amount of hydrolyzate, and the right value indicates the total amount of related substances.
• the fesoterodine fumarate-containing preparation of Example 3 containing lactose hydrate is more stable than the fesoterodine fumarate-containing preparation of Example 3, in which anhydrous lactose is used. It became clear that it showed sexuality. It was also revealed that the fesoterodine fumarate-containing preparation of Example 3 containing anhydrous lactose exhibits higher stability than the fesoterodine fumarate-containing preparations of Reference Example 1 and Example 1.
• the fesoterodine fumarate-containing formulation of Example 2 which contained anhydrous lactose in the granules
• Example 4 which contained lactose hydrate in the granules. It was found that the soterodine fumarate-containing formulation also exhibited equivalent stability.
• fesoterodine fumarate-containing preparation of Example 2 which contains lactose hydrate outside the granules
• fesoterodine fumarate of Example 5 which contains anhydrous lactose outside the granules. It was found that the formulations containing the drug also exhibited the same stability.
• lactose may be anhydrous or hydrate when using the direct compression method or dry granulation method.
• the left value in each column indicates the amount of hydrolyzate, and the right value indicates the total amount of related substances.
• the amount of anhydrous lactose was increased and the amount of crystalline cellulose was reduced. It was found to exhibit stability equivalent to that of salt-containing preparations.
• the fesoterodine fumarate-containing preparation of Example 2 containing polyvinyl alcohol and the fesoterodine fumarate-containing preparation of Example 7 not containing polyvinyl alcohol exhibit equivalent stability.
• rice field Compared to the fesoterodine fumarate-containing preparation of Example 7, the amount of anhydrous lactose was reduced and the amount of crystalline cellulose was increased. It was found to exhibit stability equivalent to that of salt-containing preparations.
• the fesoterodine fumarate-containing preparation of Example 9 in which the content of glycerin fatty acid ester was twice that of the fesoterodine fumarate-containing preparation of Example 8, and the content of glycerin fatty acid ester, in which the content of glycerin fatty acid ester was 4 times. From the stability results of the fesoterodine fumarate-containing formulation of Example 10, even if the content of glycerin fatty acid ester is changed, the amount of hydrolyzate and the total amount of related substances are hardly affected, and the same stability is achieved.

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