KR101940569B1 - Pharmaceutical composition comprising bazedoxifene or a pharmaceutically acceptable salt thereof - Google Patents
Pharmaceutical composition comprising bazedoxifene or a pharmaceutically acceptable salt thereof Download PDFInfo
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- KR101940569B1 KR101940569B1 KR1020170063942A KR20170063942A KR101940569B1 KR 101940569 B1 KR101940569 B1 KR 101940569B1 KR 1020170063942 A KR1020170063942 A KR 1020170063942A KR 20170063942 A KR20170063942 A KR 20170063942A KR 101940569 B1 KR101940569 B1 KR 101940569B1
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- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid, pantothenic acid
- A61K31/198—Alpha-aminoacids, e.g. alanine, edetic acids [EDTA]
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- 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
- A61K31/59—Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
- A61K31/593—9,10-Secocholestane derivatives, e.g. cholecalciferol, i.e. vitamin D3
-
- 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
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
-
- 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
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2806—Coating materials
- A61K9/2833—Organic macromolecular compounds
- A61K9/284—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone
Abstract
The present invention provides a pharmaceutical composition comprising a basic amino acid as a active ingredient and a pharmaceutically acceptable salt thereof (and optionally a vitamin D derivative) and a stabilizing agent, and does not contain an antioxidant. Since the pharmaceutical composition of the present invention can remarkably lower the generation of a soft substance originating from a pen at the time of bar administration, it has excellent stability and can therefore be useful for a long period of time.
Description
The present invention relates to a pharmaceutical composition comprising as an active ingredient a bar-cleaving ciphen or a pharmaceutically acceptable salt thereof and optionally a vitamin D derivative. More particularly, the present invention relates to a pharmaceutical composition comprising a basic aminoglycoside or a pharmaceutically acceptable salt thereof (and optionally a vitamin D derivative) as a active ingredient and a basic amino acid as a stabilizer, .
The bazedoxifene is a compound of the formula (I) wherein the chemical name is 1- [4- (2-azepan-1-yl-ethoxy) -benzyl] -2- (4-hydroxy- 5-ol, known as a selective estrogen receptor modulator. Bar adipocyte is in the form of acetate, which is used to treat osteoporosis in postmenopausal women [Vivienne TM (Korea Pfizer)]. VivienneTM TM contains ascorbic acid to ensure stability of baracetate penacetate but has a somewhat shorter period of use of 18 months due to its low stability.
Korean Patent Registration No. 10-1584674 (WO 2007/024961) discloses a non-aqueous pharmaceutical composition containing 15% by weight or less of an antioxidant such as ascorbic acid and a preparation method without containing a surfactant .
In addition, U.S. Patent Publication No. US2011 / 0165241 discloses that there is a problem that a tablet composition containing a basilixin acetic acid salt, ascorbic acid, and hydroxypropylmethylcellulose shows a decrease in dissolution stability during long-term storage . U.S. Patent Publication No. US2011 / 0165241 discloses the use of vitamin E, vitamin E TPGS, propyl gallate, citric acid or butylated hydroxyanisole / butylated hydroxytoluene instead of ascorbic acid as a means for solving the problem .
In addition, Korean Patent Laid-Open Publication No. 10-2007-0018900 (WO 2005/099677) discloses a solid dispersion containing a benzoxifenacetic acid salt for improving bioavailability.
However, when a solid preparation containing bar steroid ciphen or a pharmaceutically acceptable salt thereof is stored without using a stabilizing agent such as an antioxidant, The substance is out of the reference range. In addition, solid preparations containing a bar stabilizing cine or a pharmaceutically acceptable salt thereof together with a stabilizer such as an antioxidant have a relatively low stability (that is, a short use period of 18 months) so that they can be stored for a long period of time Lt; RTI ID = 0.0 > and / or < / RTI >
The present inventors have carried out various studies to develop a solid preparation containing an improved ciprofen or a pharmaceutically acceptable salt thereof with improved stability. In particular, the present inventors have conducted various studies to develop a pharmaceutical agent capable of improving the stability by minimizing the generation of a soft substance derived from a pen when a bar is taken for a long period of time. As a result, when a specific stabilizing agent, that is, a basic amino acid is used as a stabilizer instead of an antioxidant such as ascorbic acid, vitamin E, and butylated hydroxytoluene conventionally used as a stabilizer, Can be significantly lowered. In addition, it has been found that even in the case of a preparation containing vitamin D derivatives for osteoporosis patients whose vitamin D intake is insufficient, the basic amino acid can remarkably lower the generation of the pendant derived from the pen when the bar is removed.
Accordingly, it is an object of the present invention to provide a pharmaceutical composition comprising a basic aminoglycoside or a pharmaceutically acceptable salt thereof (and optionally a vitamin D derivative) and a basic amino acid as a stabilizer, which does not comprise an antioxidant .
According to one aspect of the present invention, there is provided a pharmaceutical composition comprising as an active ingredient a bar-cleaving ciphen or a pharmaceutically acceptable salt thereof; And a basic amino acid as a stabilizer, and is free from an antioxidant.
The pharmaceutical composition of the present invention can contain, as active ingredients, colecalciferol, calcitriol, calcipotriol, tacalcitol, maxacalcitol, paricalcitol, ), And seocalcitol. ≪ RTI ID = 0.0 > [0040] < / RTI >
In the pharmaceutical composition of the present invention, the pharmaceutically acceptable salt of the bar remodeling cigarette may be penacetic acid salt at the time of bar administration, and the vitamin D derivative may be cholecalciferol.
In the pharmaceutical composition of the present invention, the basic amino acid may be selected from the group consisting of histidine, arginine, and lysine, preferably histidine. The basic amino acid may be present in the range of 0.1 to 20.0 wt%, preferably 0.5 to 5 wt%, based on the total weight of the composition.
The pharmaceutical composition of the present invention can be used as a pharmaceutical composition containing lactose, mannitol, isomalt, microcrystalline cellulose, dextran, maltodextrin, sorbitol, glucose, pregelatinized starch, potato starch, corn starch, light anhydrous silicic acid, colloidal silicon dioxide, A diluent selected from the group consisting of calcium, carboxymethylcellulose, carboxyethylcellulose, hydroxyethylcellulose, and magnesium aluminum silicate; At least one disintegrant selected from the group consisting of starch, pregelatinized starch, sodium starch glycolate, croscarmellose sodium, crospovidone, carboxymethylcellulose calcium, carboxymethylcellulose sodium, alginic acid, and sodium alginate; And stearic acid or its salts, talc, magnesium / aluminum silicate, glyceryl behenate, hard castor oil, vegetable castor oil, polyethylene glycol, glyceryl monostearate, and sucrose stearic acid And at least one surfactant selected from the group consisting of esters. For example, the pharmaceutical compositions of the present invention may have the form of tablets, which may be further film coated.
In one embodiment, the pharmaceutical composition of the present invention comprises 22.6 mg of penic acid acetate per bar, 10.0 to 90.0 mg of pregelatinized starch, 26.4 to 199.4 mg of microcrystalline cellulose, 1.0 to 15.0 mg of colloidal silicon dioxide, 15.0 mg of lactose monohydrate, The pharmaceutical composition may be in the form of a tablet containing 131.1 mg, histidine 0.5 to 20.0 mg, sodium starch glycolate 3.0 to 26.0 mg, and sodium stearyl fumarate 2.0 to 15.0 mg, preferably polyvinyl alcohol And a coating layer formed on the tablet.
In another embodiment, the pharmaceutical composition of the present invention comprises 22.6 mg of penic acid acetate per bar, 800 to 5600 IU of cholecalciferol, 10.0 to 90.0 mg of pregelatinized starch, 26.38 to 199.38 mg of microcrystalline cellulose, The pharmaceutical composition may be in the form of a tablet containing 1.0 to 15.0 mg of lactose, 15.0 to 118.0 mg of lactose, 0.5 to 20.0 mg of histidine, 3.0 to 26.0 mg of sodium starch glycolate, and 2.0 to 15.0 mg of sodium stearyl fumarate, May be a pharmaceutical composition in the form of a skin-cleanser in which a film coating layer containing polyvinyl alcohol is formed on the tablet.
When a specific stabilizing agent, that is, a basic amino acid, is used as a stabilizer instead of an antioxidant such as ascorbic acid, vitamin E and butylated hydroxytoluene conventionally used as a stabilizer, It can be lowered by the present invention. It has also been found by the present invention that, even in the case of a preparation further containing a vitamin D derivative, the basic amino acid can significantly reduce the generation of the pendent originating from the pen at the time of bar removal. Therefore, a single preparation containing the bar-treatment ciphen or its pharmaceutically acceptable salt according to the present invention as an active ingredient and the bar-cleansing ciphen or its pharmaceutically acceptable salt and vitamin D derivative according to the present invention, Can have useful stability for a long period of time.
The present invention relates to a pharmaceutical composition comprising as an active ingredient a bar-cleaving ciphen or a pharmaceutically acceptable salt thereof; And a basic amino acid as a stabilizer, and does not contain an antioxidant.
In addition, the pharmaceutical composition of the present invention can contain, as active ingredients, colecalciferol, calcitriol, calcipotriol, tacalcitol, maxacalcitol, paricalcitol, and seocalcitol. The vitamin D derivative may further include one or more vitamin D derivatives selected from the group consisting of paricalcitol, and seocalcitol.
In the pharmaceutical composition of the present invention, the pharmaceutically acceptable salt of the bar remodeling cine may be, but is not limited to, penic acid acetic acid salt at the time of bar removal. The bar-cleansing cine or its pharmaceutically acceptable salt may be used in a therapeutically effective amount, for example in the range of 1 to 100 mg, preferably in the range of 10 to 30 mg, , More preferably about 20 mg (about 22.6 mg as a barcodeine cyphenate salt). In addition, the vitamin D derivative may preferably be cholecalciferol. The vitamin D derivatives such as cholecalciferol can be used in therapeutically effective amounts, for example in the range of 50 to 5,600 IU per unit of agent, preferably in the range of 400 to 2,000 IU. About 800 IU of cholecalciferol has a mass of about 0.02 to 8 mg according to the activity per gram of cholecalciferol (40,000,000 IU / g to 100,000 IU / g).
The pharmaceutical composition of the present invention may contain conventional antioxidants such as ascorbic acid or a salt thereof (e.g., sodium salt, palmitate), vitamin E, propyl gallate, butylated hydroxytoluene (BHT ), Butylated hydroxyanisole (BHA), etc.), it is possible to remarkably lower the generation of the pendant originating from the pen at the time of bar removal by containing a basic amino acid stabilizer. As described in the following test example, a preparation containing a basic amino acid such as histidine as a stabilizer minimizes the generation of a substance for a long period of time (for example, about 4 weeks) under severe conditions (60 ° C, 75% RH) And thus exhibits excellent stability. The basic amino acid may be selected from the group consisting of histidine, arginine, and lysine, preferably histidine. The basic amino acid may be present in the range of 0.1 to 20.0 wt%, preferably 0.5 to 5 wt%, based on the total weight of the composition.
The pharmaceutical composition of the present invention may contain additives such as diluents, disintegrants, lubricants and the like commonly used in the field of pharmaceuticals. Examples of the diluent include lactose (including hydrate such as lactose hydrate), mannitol, isomalt, microcrystalline cellulose, dextran, maltodextrin, sorbitol, glucose, pregelatinized starch, potato starch, corn starch, Silicon dioxide, crystalline cellulose, anhydrous calcium phosphate, carboxymethylcellulose, carboxyethylcellulose, hydroxyethylcellulose, and magnesium aluminum silicate. Examples of the disintegrant include starch, pregelatinized starch, sodium starch glycolate, croscarmellose sodium, crospovidone, carboxymethylcellulose calcium, carboxymethylcellulose sodium, alginic acid, sodium alginate and the like. Examples of the lubricant include sodium stearyl fumarate, colloidal silicon dioxide, silica, stearic acid or a salt thereof, talc, magnesium / aluminum silicate, glyceryl behenate, hard castor oil, vegetable castor oil, polyethylene glycol, glyceryl monostearate Sucrose stearic acid ester, and the like. For example, the pharmaceutical compositions of the present invention may comprise a combination of lactose and microcrystalline cellulose as diluents; A combination of pregelatinized starch and starch glycolic acid sodium as a disintegrant; As a lubricant, a combination of sodium stearyl fumarate and colloidal silicon dioxide. The amount of the additive such as the diluent, disintegrant, lubricant and the like is not particularly limited and may be suitably selected by those skilled in the art. For example, the diluent may be in the range of 30 to 90 wt.%, The disintegrant may be in the range of 1 to 20 wt.% Based on the total weight of the composition, the lubricant may be in the range of 0.5 to 5 wt. But is not limited thereto.
The pharmaceutical composition of the present invention may be a solid dosage form such as an acid, a granule, a capsule, or a tablet, preferably in the form of a capsule or a tablet, and more preferably in the form of a tablet. In addition, the pharmaceutical composition of the present invention may be in the form of a shellac-tablet, for example, a film-coating base containing polyvinyl alcohol (for example, Opadyl TM 85F42129 (Colorcona) - It can be in the form of tablets.
In one embodiment, the pharmaceutical composition of the present invention comprises 22.6 mg of penic acid acetate per bar, 10.0 to 90.0 mg of pregelatinized starch, 26.4 to 199.4 mg of microcrystalline cellulose, 1.0 to 15.0 mg of colloidal silicon dioxide, 15.0 mg of lactose monohydrate, The pharmaceutical composition may be in the form of a tablet containing 131.1 mg, histidine 0.5 to 20.0 mg, sodium starch glycolate 3.0 to 26.0 mg, and sodium stearyl fumarate 2.0 to 15.0 mg, preferably polyvinyl alcohol And a coating layer formed on the tablet.
In another embodiment, the pharmaceutical composition of the present invention comprises 22.6 mg of penic acid acetate per bar, 800 to 5600 IU of cholecalciferol, 10.0 to 90.0 mg of pregelatinized starch, 26.38 to 199.38 mg of microcrystalline cellulose, The pharmaceutical composition may be in the form of a tablet containing 1.0 to 15.0 mg of lactose, 15.0 to 118.0 mg of lactose, 0.5 to 20.0 mg of histidine, 3.0 to 26.0 mg of sodium starch glycolate, and 2.0 to 15.0 mg of sodium stearyl fumarate, May be a pharmaceutical composition in the form of a skin-cleanser in which a film coating layer containing polyvinyl alcohol is formed on the tablet.
The method of preparing a pharmaceutical composition of the present invention comprises the steps of: mixing a bar or a pharmaceutically acceptable salt thereof (and optionally a vitamin D derivative), a basic amino acid, and a pharmaceutically acceptable additive; And filling the resulting mixture into a capsule to obtain a capsule, or tableting the resulting mixture to obtain a tablet. Further, as described above, if necessary, a step of forming a film coating layer with a film-coating base containing polyvinyl alcohol (for example, Opadry TM 85F42129 (Colorcona)) may be further included. The mixing may be performed through a plurality of mixing processes in which all the components are mixed through one mixing process or a mixture of a plurality of components is mixed with the remaining components. The mixing process, the capsule filling process, the tableting process, the film coating process, and the like may be performed according to a conventional method known in the pharmaceutical industry.
Hereinafter, the present invention will be described in more detail through examples and test examples. However, the following examples and test examples are provided for illustrating the present invention, and the present invention is not limited thereto.
Example One. Bar Admiral Pien Preparation of tablets containing acetic acid salts
Tablets containing the penic acid acetic acid salt according to the contents and compositions shown in Table 1 below were prepared. The content of each component in Table 1 represents the refined sugar content (mg). (22.6 mg per tablet, 20 mg as a bar sterilizer), colloidal silicon dioxide and histidine, followed by addition of microcrystalline cellulose, pregelatinized starch and sodium starch glycolate, followed by mixing. The resulting mixture was sieved with a 30-mesh sieve, and the lactose hydrate was further added thereto and mixed. The resulting mixture was mixed with sodium stearyl fumarate. The resulting mixture was triturated to produce 290 mg of a tablet. The obtained tablets were coated with Opadry TM 85F42129 (Colorcon) to prepare film-coated tablets.
Example 2. Bar Admiral Pien Acetic acid salts and Cholecalciferol (40,000,000 IU / g) Preparation of tablets containing
Tablets containing barmacytials phenacetate and cholecalciferol powder (40,000,000 IU / g) were prepared according to the contents and compositions in Table 2 below. The content of each component in Table 2 represents the refined sugar content (mg). After mixing cholecalciferol and microcrystalline cellulose (about 9.0% by weight of the total amount used), the bar-cleavage phenylacetate (22.6 mg per tablet, 20 mg as bar celecoxib), colloidal silicon dioxide and histidine were added And then microcrystalline cellulose (about 91.0% by weight of the total amount used), pregelatinized starch and starch glycolic acid sodium were further added and mixed. The resulting mixture was sieved with a 30 mesh sieve, and lactose hydrate was added and mixed. The resulting mixture was mixed with sodium stearyl fumarate. The resulting mixture was triturated to produce 290 mg of a tablet. The obtained tablets were coated with Opadry TM 85F42129 (Colorcon) to prepare film-coated tablets.
Example 3. Bar Admiral Pien Acetic acid salts and Cholecalciferol (100,000 IU / g) Preparation of tablets containing
Tablets containing barmacytial penacetate and cholecalciferol powder (100,000 IU / g) were prepared according to the contents and compositions in Table 3 below. The content of each component in Table 3 represents the refined sugar content (mg). (22.6 mg per tablet, 20 mg as a bar steroid), colloidal silicon dioxide and histidine were mixed and then mixed with concentrated cholecalciferol (8.0 mg per tablet, 800 IU as vitamin D3) Thereafter, microcrystalline cellulose, pregelatinized starch and sodium starch glycolate were further added and mixed. The resulting mixture was sieved with a 30 mesh sieve, and lactose hydrate was added and mixed. The resulting mixture was mixed with sodium stearyl fumarate. The resulting mixture was triturated to produce 290 mg of a tablet. The obtained tablets were coated with Opadry TM 85F42129 (Colorcon) to prepare film-coated tablets.
Comparative Example One. Bar Admiral Pien Preparation of tablets containing acetic acid salts
(Comparative Example 1-1), inorganic salt of calcium carbonate (Comparative Example 1-2), antioxidant ascorbic acid (Comparative Example 1-3), or butylated hydroxytoluene (Comparative Example 1) instead of histidine, -4) was used in place of the antimicrobial agent, the tablets containing the penic acid acetic acid salt were prepared in the same manner as in Example 1-1. In addition, tablets (Comparative Example 1-5) containing baracetic acid phenacetate were prepared in the same manner as in Example 1-1, except that histidine was not used for comparison. The compositions of Comparative Examples 1-1 to 1-5 are shown in Table 4 below. The content of each component in Table 4 represents the content of refined sugar (mg).
Comparative Example 2. Bar Admiral Pien Acetic acid salts and Cholecalciferol Preparation of tablets containing
(Comparative Example 2-1) which is an amino alcohol instead of histidine, calcium carbonate (Comparative Example 2-2) which is an inorganic salt, ascorbic acid (Comparative Example 2-3) or butylated hydroxytoluene (Comparative Example 2 -4) was used in place of benzalkonium chloride, tablets containing the penic acid acetic acid salt and cholecalciferol were prepared in the same manner as in Example 2-1. In addition, tablets (Comparative Example 2-5) containing a penic acid acetic acid salt and cholecalciferol were prepared in the same manner as in Example 2-1, except that histidine was not used for comparison. The compositions of Comparative Examples 2-1 to 2-5 are shown in Table 5 below. The content of each component in Table 5 represents the refined sugar content (mg).
Test Example One. Bar Admiral Pien Evaluation of the stability of tablets containing acetic acid salts
The initial suppositories for the tablets of Example 1-1 and the tablets of Comparative Examples 1-1 to 1-6 were measured and then subjected to the conditions of opening and closing at harsh conditions (60 ° C, 75% RH) , The content of the softening substance derived from the pan-decongestant was measured. The content of the above-mentioned substance was measured by HPLC using standard solution and standard solution. The standard solution was prepared by taking the phenacetate standard as a standard solution in a test solvent (25 mM phosphate buffer + 4.5 mM nucleic acid sulfonic acid (pH 3.0 ± 0.1) / acetonitrile (50:50 ) (v: v). The test solution was prepared by taking 10 tablets each using the above-mentioned sample solvent. The HPLC conditions were as follows.
<HPLC analysis conditions>
- Detector: Ultraviolet absorptiometer (measuring wavelength: 220 nm)
Photodiode array (measuring wavelength: 200 ~ 350 nm)
- Column: C18, 5 um, 150 X 4.6 mm column
- Column temperature: 30 ° C
- Mobile phase: 25 mM phosphate buffer (pH 3.0) / acetonitrile (68:32) (v / v)
- Flow rate: about 1.5 mL / min
The results of the measurement of the content of the flexible material in the severe condition as described above are shown in Table 6 below.
As can be seen from the results of the above Table 6, the tablets of Example 1-1 show a remarkably low production of a flexible substance, while containing an amino alcohol, an inorganic salt, or an antioxidant or containing a stabilizer The tablets of the comparative examples all showed a high content of the flexible material. Therefore, it can be confirmed that the tablets obtained according to the present invention exhibit excellent stability by minimizing the production of a flexible substance.
Test Example 2. Bar Admiral Pien Acetic acid salts and Cholecalciferol Evaluation of the stability of tablets containing
The initial suppositories for the tablets of Example 2-1 and the tablets of Comparative Examples 2-1 to 2-6 were measured and then subjected to an open and a close condition at harsh conditions (60 ° C, 75% RH) , The content of the softening substance derived from the pan-decongestant was measured. The content of the above-mentioned flexible substance was measured in the same manner as in Test Example 1, and the results are shown in Table 7 below.
As can be seen from the results of Table 7 above, the tablets of Example 2-1 had the remarkably low production of the suppositories as in the tablets of Example 1-1, whereas the tablets of Examples 2-1, The tablets of the comparative examples which did not contain the agent or did not contain the stabilizer all showed a high content of the flexible substance. Therefore, it can be confirmed that the tablets obtained according to the present invention exhibit excellent stability by minimizing the production of a flexible substance.
Claims (14)
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PCT/KR2018/005470 WO2018216933A1 (en) | 2017-05-24 | 2018-05-14 | Pharmaceutical composition containing bazedoxifene or pharmaceutically acceptable salt |
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CN101977897A (en) * | 2008-02-11 | 2011-02-16 | 惠氏有限责任公司 | Methods of preparing polymorphic form a of bazedoxifene acetate |
KR101806782B1 (en) * | 2015-09-07 | 2018-01-10 | 주식회사 경보제약 | Method for the preparation of high purity Bazedoxifene Acetate |
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