WO2015108392A1 - Petit comprimé pharmaceutique contenant de l'ésoméprazole - Google Patents

Petit comprimé pharmaceutique contenant de l'ésoméprazole Download PDF

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Publication number
WO2015108392A1
WO2015108392A1 PCT/KR2015/000549 KR2015000549W WO2015108392A1 WO 2015108392 A1 WO2015108392 A1 WO 2015108392A1 KR 2015000549 W KR2015000549 W KR 2015000549W WO 2015108392 A1 WO2015108392 A1 WO 2015108392A1
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WIPO (PCT)
Prior art keywords
small pharmaceutical
small
tablet
cellulose
pharmaceutical
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PCT/KR2015/000549
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English (en)
Korean (ko)
Inventor
신용관
이승언
이지은
송세현
손세일
이홍우
Original Assignee
대원제약주식회사
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Publication of WO2015108392A1 publication Critical patent/WO2015108392A1/fr

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    • 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
    • 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
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • 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
    • 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
    • A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
    • 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
    • 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
    • A61K9/2846—Poly(meth)acrylates

Definitions

  • the present invention relates to small pharmaceutical tablets containing esomeprazole with improved ease of manufacture, ease of taking and patient compliance.
  • the present invention relates to a small pharmaceutical tablet containing esomeprazole in the same amount as a conventional pharmaceutical formulation, but having a reduced size (volume) of the final tablet.
  • the present invention also relates to a pharmaceutical tablet in which the stability is increased by maximizing the degradation of esomeprazole while constituting the formulation as a small tablet.
  • Eomeprazole is (S) -5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl) methylsulfinyl] -3H-benzoimidazole, which is a peptic ulcer, gastric or esophagus Proton pump inhibitors used in reflux disease and the like.
  • esomeprazole is susceptible to degradation or modification in acidic and neutral media, and more particularly, it is known that the degradation half-life of esomeprazole in aqueous solutions with a pH value of 3 or less is less than 10 minutes. Decomposition of esomeprazole is facilitated by acidic compounds and is affected by moisture, heat and organic solvents and light. Therefore, there has been a lot of demands for stable esomeprazole formulations, and to overcome these problems, capsules containing conventional enteric skin pellet formulations have been developed.
  • Korean Patent Publication No. 10-1996-0704532 discloses an oral pharmaceutical multi-unit of omeprazole comprising individually enteric-laminated unit pellets and tablet excipients of a core material coated with one or more layers. Tablet formulations are disclosed.
  • the manufacturing cost increases and coating success rate is very low because special equipment is used to prepare the individual enteric-laminated unit pellets of the core material coated with one or more layers of omeprazole.
  • the size of the finished tablet is very large.
  • Korean Patent Publication No. 10-1996-0003605 discloses a method for producing an omeprazole core composition prepared by using omeprazole as an active ingredient and adding and mixing beta-cyclodextrin and sodium hydroxide as a stabilizing component to prepare a solid dispersion.
  • the invention described in the patent has a problem of using sodium hydroxide, which is harmful to the human body, and as in the case of Patent Publication No. 10-1996-0704532, since the core composition is manufactured, it does not overcome the problem of an increase in manufacturing cost and an increase in formulation size. It was.
  • the process of preparing a solid dispersion includes the process of dissolving omeprazole as a main component in a solvent, and thus requires a special stabilizer such as sodium hydroxide to stabilize the omeprazole.
  • the inventors of the present invention have completed the present invention regarding a small pharmaceutical tablet that can be prepared through an easy manufacturing process and shows biological equivalence with a conventional formulation, after studying to improve the problems of the prior art.
  • An object of the present invention is to provide a small pharmaceutical tablet containing esomeprazole with improved ease of manufacture, ease of use, and patient compliance, despite the reduced size, it is possible to ensure the safety of the active ingredient, existing commercial products and bioavailability It is to provide this equivalent pharmaceutical tablet.
  • the present invention provides a small pharmaceutical tablet with a total volume of 0.4 mL or less as a small tablet containing eomeprazole as an active ingredient.
  • Esomeprazole small pharmaceutical tablet according to the present invention is easy to manufacture, while showing bioequivalence with commercially available esomeprazole pharmaceutical tablets prepared as core granules, the size of the preparation is significantly smaller than that of conventional formulations to improve the convenience and patient compliance It is effective.
  • FIG. 1 is a diagram showing the results of a bioequivalence test of esomeprazole small pharmaceutical tablet of the present invention.
  • Figure 2 is a diagram comparing the size of Nexium tablets commercially available tablets and small tablets of esomeprazole of the present invention.
  • Figure 3 is a comparison of the size of esomeprazole small pharmaceutical tablets of the present invention and capsules commercially available is 40mg.
  • the present invention provides a small pharmaceutical tablet containing esomeprazole as an active ingredient.
  • esomeprazole is a concept including all of esomeprazole or a pharmaceutically acceptable salt thereof or a hydrate thereof.
  • the term "small” refers to a concept compared to the size of tablets made from existing esomeprazole capsules or core granules, which means that the size is small compared to conventionally known pharmaceutical products.
  • the volume of the pharmaceutical tablet is 0.4mL or less, and when converted to weight, it corresponds to 0.35g to 0.45g.
  • the volume 0.4mL defined as the small pharmaceutical tablet may be a value rounded off to two decimal places. Accordingly, pharmaceutical agents corresponding to the range of 0.35 ml to 0.45 mL are also included in the scope of the present invention.
  • the volume of the small pharmaceutical tablet is 0.4 mL or less.
  • the volume of the pharmaceutical tablets exceeds 0.4mL, the size of the tablets is increased, and thus, especially when the elderly or children take the pharmaceutical tablets, they may cause swallowing or vomiting.
  • Eomeprazole is a proton pump inhibitor. It is a prescription frequently used in chronic patients such as gastric ulcer, duodenal ulcer and gastritis. As the patient compliance decreases, the treatment efficiency of the disease may be significantly reduced.
  • the small pharmaceutical tablet of the present invention contains a certain amount of magnesium oxide (MgO).
  • the magnesium oxide is preferably 0.1 to 1 parts by weight per 1 part by weight of omeprazole. Excessive use of magnesium oxide can cause diarrhea side effects.
  • the inventors found that tablets containing esomeprazole and magnesium oxide did not affect safety and bioavailability even when the tablet volume was less than 0.4 mL. This is considered that, in the case of tableting by simply increasing the pressure while maintaining the existing prescription to simply reduce the size of the tablet, it adversely affects the safety of the final manufactured drug, or affects dissolution and lowers bioavailability. It is a new knowledge.
  • the small pharmaceutical agent of the present invention may further include an excipient.
  • the excipient is microcrystalline cellulose, povidone, povidone, crospovidone, L-arginine, sodium stearyl fumarate, polyvinyl alcohol, polymethacryl It may be at least one selected from the group consisting of methacrylate (Polymethacrylate).
  • Small pharmaceutical agents of the present invention may further comprise a diluent, binder, disintegrant or glidant generally used in the art.
  • the diluent may be at least one selected from the group consisting of lactose, sucrose, crystalline cellulose, cellulose, powdered, and siliconized microcrystalline cellulose.
  • the binder may be at least one selected from the group consisting of povidone, hypromellose, hydroxypropyl cellulose, carboxymethyl cellulose, sodium zein, and starch. have.
  • the disintegrant is Carboxymethyl cellulose (calcium), Croscarmellose sodium, Starch, Sodium starch glycolate, Low-substituted hydroxypropyl cellulose (Hydroxypropyl cellulose, low) -substituted) may be one or more selected from the group consisting of.
  • the lubricant may be one or more selected from the group consisting of talc, magnesium stearate, silicon dioxide, stearic acid, and hydrogenated oil.
  • the small pharmaceutical tablet of the present invention may include an enteric coating layer.
  • the coating base used in the enteric coating layer is at least one selected from the group consisting of phthalic hydroxypropylmethylcellulose phthalate, hydroxypropylmethylcellulose acetate succinate, and polymethacrylate. This is preferred.
  • Uncoated tablet was prepared in the same manner as in Example 1 except that the magnesium oxide content was mixed at 8 mg.
  • the volume of the uncoated tablet prepared was 0.29 mL.
  • Uncoated tablets were prepared in the same manner as in Example 1, except that the magnesium oxide content was 20 mg.
  • the volume of the prepared uncoated tablet was 0.30 mL.
  • Uncoated tablets were prepared in the same manner as in Example 1 except that the magnesium oxide content was 40 mg.
  • the volume of the uncoated tablet prepared was 0.32 mL.
  • Uncoated tablets were prepared in the same manner as in Example 1, except for magnesium oxide.
  • the volume of the uncoated tablet prepared was 0.27 mL.
  • Uncoated tablets were prepared in the same manner as in Example 1, except that 20 mg of calcium hydroxide was mixed instead of magnesium oxide.
  • the volume of the prepared uncoated tablet was 0.30 mL.
  • Uncoated tablets were prepared in the same manner as in Example 1 except that 20 mg of sodium hydrogen phosphate was mixed instead of magnesium oxide.
  • the volume of the prepared uncoated tablet was 0.30 mL.
  • Uncoated tablets were prepared in the same manner as in Example 1, except that 20 mg of calcium carbonate was mixed instead of magnesium oxide.
  • the volume of the prepared uncoated tablet was 0.30 mL.
  • Uncoated tablets were prepared in the same manner as in Example 1, except that 20 mg of potassium hydrogen carbonate was mixed in place of magnesium oxide.
  • the volume of the prepared uncoated tablet was 0.30 mL.
  • Comparative Example 6 was prepared by referring to Korean Unexamined Patent Publication No. 10-2009-0033000. Add a solution of povidone (40 mg) and NaOH (1.8 mg) in an appropriate amount of ethanol, mix well, add Esmeprazole Magnesium Hydrate (43.38 mg) to dissolve completely, and add some magnesium oxide (50 mg) to the solution. . The solution was sprayed onto colloidal silicon dioxide (12.5 mg) and magnesium oxide (50 mg) in a fluidized bed to prepare granules. The granulated tablets were mixed with microcrystalline cellulose (265.7 mg), crospovidone (25.0 mg) and magnesium stearate (5.0 mg) to prepare uncoated uncoated tablets.
  • HPMC P HP-50
  • the ratio of the decomposition amount per unit time of the undisassembled, ie stable, esmeprazole magnesium hydrate of each Example and the comparative example to the unit amount decomposition time of the pure esomeprazole magnesium hydrate was calculated as follows.
  • Examples 1 to 4 of the small pharmaceutical tablet according to the present invention can be seen that the decomposition rate is significantly reduced compared to Comparative Examples 1 to 5 are formulated into a stable someprazole formulation.
  • the size of the enteric-coated tablet of Example 5 and 40 mg of Nexium tablet (Korea AstraZeneca), which is a commercially available esomeprazole tablet, and 40 mg of Esomer capsule (esque chemical) were separately observed.
  • the volume of the Nexium tablet was 0.52 ml (weight 570 mg) and the volume of the enteric coated tablet according to Example 5 was 0.37 ml (weight was 370 mg).
  • the small pharmaceutical tablet according to the present invention was found to be a significantly smaller form than the commercial formulation. (See Figures 2 and 3)
  • Example 5 A biological equivalence test was performed on Example 5 and Nexium tablet 40 mg (AstraZeneca Korea) on 60 healthy adult volunteers according to the 2 ⁇ 2 cross-test.
  • the small pharmaceutical tablet according to the present invention was found to be biologically equivalent to a commercial tablet. (See Figure 1)
  • Example 5 Dose convenience tests were conducted in 30 patients on Example 5 prepared in accordance with the present invention and on commercially available formulations (Nexium tablet 40 mg, Esomemed capsule 40 mg). Patients were randomly assigned to one group of 10 people, and each group was to receive the formulation of Example 5, Nexium tablets, and capsules of Esomed. Dose convenience was calculated by grading the degree of ease of throbbing when the tablet was swallowed by 1: very hard / 2: hard / 3: normal / 4: easy / 5: very easy scoring. The test results are shown in the table below.
  • Example 5 As shown in Table 2, the score for the convenience of taking the pharmaceutical tablet of Example 5 according to the present invention was found to be the highest. This is because Example 5 is smaller in size than commercially available tablets, and it is determined that the capsules, which are disadvantages of commercially available capsules, adhere to the esophagus to remove unpleasant elements.
  • Example 5 prepared according to the present invention and commercially available formulations (Nexium tablet 40 mg, Esomed capsule 40 mg), 30 patients were asked to select a preferred dosage form. The test results are shown in the table below.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • Medicinal Preparation (AREA)

Abstract

La présente invention concerne un petit comprimé pharmaceutique contenant de l'ésoméprazole étant plus facile à préparer, plus commode à doser, et permettant d'améliorer l'observance des patients. Le petit comprimé pharmaceutique d'ésoméprazole selon la présente invention est facile à préparer et a une taille de formulation considérablement miniaturisée comparé à la formulation classique, tout en présentant une équivalence biologique avec la formulation pharmaceutique d'ésoméprazole disponible dans le commerce et préparée par un cœur granulé, et possède ainsi les effets d'amélioration de la commodité de dosage et de l'observance des patients.
PCT/KR2015/000549 2014-01-20 2015-01-20 Petit comprimé pharmaceutique contenant de l'ésoméprazole WO2015108392A1 (fr)

Applications Claiming Priority (2)

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KR10-2014-0006568 2014-01-20
KR1020140006568A KR101658275B1 (ko) 2014-01-20 2014-01-20 에스오메프라졸 함유 소형 의약정제

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WO2015108392A1 true WO2015108392A1 (fr) 2015-07-23

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017185123A1 (fr) * 2016-04-29 2017-11-02 Alan Thompson Composition vétérinaire
US10736855B2 (en) 2016-02-25 2020-08-11 Dexcel Pharma Technologies Ltd. Compositions comprising proton pump inhibitors

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102432084B1 (ko) 2021-11-16 2022-08-12 알리코제약(주) S-오메프라졸을 함유하는 안정성이 개선되고 소형화된 정제

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20090033000A (ko) * 2007-09-28 2009-04-01 주식회사 씨티씨바이오 에소메프라졸 함유 약학 조성물
US20110177164A1 (en) * 2008-10-06 2011-07-21 Gopal Rajan Pharmaceutical Compositions Comprising Amorphous Esomeprazole, Dosage Forms And Process Thereof

Family Cites Families (2)

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Publication number Priority date Publication date Assignee Title
GB2189698A (en) 1986-04-30 1987-11-04 Haessle Ab Coated omeprazole tablets
KR960003605A (ko) 1994-07-19 1996-02-23 김충식 해조류(海藻類)성분이 함유된 저염(低鹽) 재제염의 제조방법

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20090033000A (ko) * 2007-09-28 2009-04-01 주식회사 씨티씨바이오 에소메프라졸 함유 약학 조성물
US20110177164A1 (en) * 2008-10-06 2011-07-21 Gopal Rajan Pharmaceutical Compositions Comprising Amorphous Esomeprazole, Dosage Forms And Process Thereof

Non-Patent Citations (2)

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Title
ANROOP B NAIR ET AL.: "Formulation and evaluation of enteric coated tablets of proton pump inhibitor", JOURNAL OF BASIC AND CLINICAL PHARMACY, vol. 1, 2010, pages 215 - 221, XP055214221 *
TUSHAR G. RUKARI ET AL.: "Formulation and evaluation of esomerazole delayed release tablets", ASIAN JOURNAL OF PHARMACEUTICAL AND CLINICAL RESEARCH, vol. 6, no. ISSUE, 2013, pages 121 - 125, XP055214300 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10736855B2 (en) 2016-02-25 2020-08-11 Dexcel Pharma Technologies Ltd. Compositions comprising proton pump inhibitors
WO2017185123A1 (fr) * 2016-04-29 2017-11-02 Alan Thompson Composition vétérinaire

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KR20150086653A (ko) 2015-07-29

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