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WO2013077823A1 - Préparations à dispersion rapide contenant du natéglinide - Google Patents

Préparations à dispersion rapide contenant du natéglinide Download PDF

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Publication number
WO2013077823A1
WO2013077823A1 PCT/TR2012/000168 TR2012000168W WO2013077823A1 WO 2013077823 A1 WO2013077823 A1 WO 2013077823A1 TR 2012000168 W TR2012000168 W TR 2012000168W WO 2013077823 A1 WO2013077823 A1 WO 2013077823A1
Authority
WO
WIPO (PCT)
Prior art keywords
formulation according
nateglinide
range
formulation
microcrystalline cellulose
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/TR2012/000168
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English (en)
Inventor
Mahmut Bilgic
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Individual
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Individual
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Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of WO2013077823A1 publication Critical patent/WO2013077823A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • 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 or pantothenic acid
    • A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
    • 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
    • A61K9/0002—Galenical forms characterised by the drug release technique; Application systems commanded by energy
    • A61K9/0007—Effervescent
    • 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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
    • 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
    • A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
    • A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches

Definitions

  • the present invention relates to pharmaceutical formulations comprising nateglinide that shall be used in the treatment of diabetes.
  • Nateglinide was first disclosed in the application numbered EP 196222. In said document, it has been disclosed that nateglinide is effective in the treatment of diabetes.
  • Nateglinide is available in 60, 120, 180 mg oral tablets on the market.
  • Nateglinide is a low water-soluble active agent. Therefore, distribution of the formulations comprising this active agent in body takes long periods of time. However, nateglinide should act shortly after taken in order to reduce blood sugar level quickly which is elevated especially after meal. In this respect, there is need for development of nateglinide formulations which disperse in a short time.
  • nateglinide is structurally an amino acid derivative.
  • Such molecules cause formation of various by-products by reacting with some excipients which are used basically in pharmaceutical technology. Therefore, problems arise in selecting the excipient and there is need to develop pharmaceutical formulations which both have appropriate physical characteristics and are stable.
  • one characteristic feature of the present invention is nateglinide formulations wherein a disintegrant combination comprising microcrystalline cellulose and croscarmellose sodium is used.
  • microcrystalline cellulose one of the components in said disintegrant composition, and the weight ratio of microcrystalline cellulose to croscarmellose sodium, the other component in the disintegrant composition, are influential on dispersion of the dosage forms prepared with the formulation obtained in water.
  • the inventors have found that use of macrocrystalline cellulose having a d 50 value in the range of 60 tolOO ⁇ , preferably in the range of 70 to 90 ⁇ ; a d 90 value in the range of 200 to 350 ⁇ , preferably in the range of 220 to 280 ⁇ gives positive results on dispersion of the formulation.
  • d 50 signifies that half of the said substance by volume has a particle size over the value stated with d 50 and the other half of the substance by volume has a particle size below the value stated with dso.
  • d 9 o signifies that 90% of the said substance by volume has a particle size below the stated value and 10% of the said substance by volume has a particle size over the stated value.
  • the present invention relates to compositions comprising nateglinide as active agent wherein a disintegrant combination comprising microcrystalline cellulose and croscarmellose sodium is used and microcrystalline cellulose comprised in said composition has a d 50 value in the range of 60 to 100 ⁇ , a devalue in the range of 200 to 350 ⁇ .
  • D 50 and d 90 values can be measured with one of the known measuring devices, for instance with a device which measures particle distribution by laser diffraction (for instance, Malvern Mastersizer etc.).
  • a device which measures particle distribution by laser diffraction for instance, Malvern Mastersizer etc.
  • pH value of microcrystalline cellulose used is also important for preventing side reactions that can occur with nateglinide.
  • the inventors have seen that use of microcrystalline cellulose having a pH value in the range of 5 to 7.5 is important for preventing undesired reactions that can occur between nateglinide and microcrystalline cellulose.
  • the present invention relates to compositions comprising nateglinide as active agent wherein a disintegrant combination comprising microcrystalline cellulose and croscarmellose sodium is used and microcrystalline cellulose comprised in said compositions has a pH value in the range of 5 to 7.5; a d 50 value in the range of 60 to 100 ⁇ ; a d 90 value in the range of 200 to 300 ⁇ .
  • the inventors have seen that bulk density of microcrystalline cellulose used is effective on flow properties of the formulation obtained.
  • the inventors have seen that the formulation obtained has a homogeneous flow in nateglinide formulations wherein microcrystalline cellulose has a bulk density in the range of 0.2 to 0.4 g cc is used.
  • the present invention relates to compositions comprising nateglinide wherein a disintegrant combination comprising microcrystalline cellulose and croscarmellose sodium is used and microcrystalline cellulose comprised in said compositions has a pH value in the range of 5 to 7.5; a bulk density value in the range of 0.2 to 0.4; a d 50 value in the range of 60 to 100 ⁇ ; a d 90 value in the range of 200 to 300 ⁇ . It has been seen that other factors playing a role on dispersion of nateglinide formulations of the present invention in a short time as desired, for instance in less than 5 minutes, are the amount of the components composing disintegrant composition and the ratio of the components to each other.
  • the ratio of microcrystalline cellulose to croscarmellose sodium composing the disintegrant composition is in the range of 5: 1 to 10: 1 by weight, preferably in the range of 6: 1 to 9: 1 by weight, more preferably in the range of 7:1 to 8.5: 1 by weight; dispersion of the dosage forms obtained from this formulation in water is performed in a short time.
  • the formulations of the present invention comprise microcrystalline cellulose in the range of 5-10% by weight, croscarmellose sodium in the range of 0.5-5% by weight in proportion to total weight of the unit dosage form.
  • the formulations prepared according to the present invention are in various dosage forms suitable for oral use, for instance in any of film coated tablet, prolonged release tablet, modified release tablet, capsule, dry powder for suspension preparation, effervescent tablet, effervescent granule, orodispersible tablet, chewable tablet, sachet forms.
  • the formulations of the present invention are preferably in tablet or film coated tablet forms, more preferably in film coated tablet form.
  • Nateglinide formulations of the present invention comprise at least one pharmaceutically acceptable excipient along with a disintegrant combination comprising microcrystalline cellulose and croscarmellose sodium.
  • At least one pharmaceutically acceptable excipient that can be used in addition to a disintegrant combination comprising microcrystalline cellulose and croscarmellose sodium in nateglinide formulations of the present invention can be selected from a group comprising diluent, binder, lubricant, flavouring agent, effervescent acid, effervescent base, glidant.
  • the binder that can be used in addition to a disintegrant combination comprising microcrystalline cellulose and croscarmellose sodium in nateglinide formulations of the present invention is selected from a group comprising carboxymethyl cellulose sodium, ethyl cellulose, gelatine, hydroxyethyl cellulose, hydroxymethyl cellulose, hypromellose, magnesium aluminium silicate, maltodextrin, methyl cellulose, povidone, starch.
  • the lubricant that can be used in addition to a disintegrant combination comprising microcrystalline cellulose and croscarmellose sodium in nateglinide formulations of the present invention is selected from a group comprising calcium stearate, magnesium stearate, polyethylene glycol, sodium benzoate, potassium benzoate, sodium lauryl sulphate, talc, stearic acid, zinc stearate.
  • the diluent that can be used in addition to a disintegrant combination comprising microcrystalline cellulose and croscarmellose sodium in nateglinide formulations of the present invention is selected from a group comprising calcium carbonate, dibasic calcium phosphate, tribasic calcium phosphate, calcium sulphate, microcrystalline cellulose, dextrose, fructose, lactitol, lactose, magnesium carbonate, magnesium oxide, maltitol, maltodextrin, maltose, mannitol, simethicone, sorbitol, starch, sodium chloride, sucrose, talc, xylitol.
  • flavouring agent that can be used in addition to a disintegrant combination comprising microcrystalline cellulose and croscarmellose sodium in nateglinide formulations of the present invention is selected from menthol, lemon, orange, vanilla, strawberry, raspberry, caramel and similar flavours.
  • the glidant that can be used in addition to a disintegrant combination comprising microcrystalline cellulose and croscarmellose sodium in nateglinide formulations of the present invention is selected from a group comprising tribasic calcium phosphate, colloidal silicone dioxide, magnesium silicate, magnesium trisilicate, talc.
  • the effervescent acid that can be used in addition to a disintegrant combination comprising microcrystalline cellulose and croscarmellose sodium in nateglinide formulations of the present invention is selected from a group comprising organic acids such as malic acid, citric acid, tartaric acid, fumaric acid.
  • the effervescent base that can be used in addition to a disintegrant combination comprising microcrystalline cellulose and croscarmellose sodium in nateglinide formulations of the present invention is selected from a group comprising the agents such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate.
  • the formulations of the present invention comprise nateglinide in the range of 5 to 35% by weight, preferably in the range of 10 to 30% by weight, more preferably in the range of 15 to 30%by weight in proportion to total weight of unit dosage amount.
  • Nateglinide comprised in the formulations of the present invention can be in crystalline or amorphous forms and/or in the form of its hydrates, solvates or a combination thereof.
  • the formulation can be produced by direct compression method or dry or wet granulation method or by using these methods consecutively in a combined form.
  • the substances comprised in the formulations are measured one by one, and mixed.
  • the dry powder obtained is compressed in tablet compression machine and formed into tablets.
  • the other substances comprised in the formulation except for the lubricant are mixed and subjected to precompression process.
  • the tablets obtained after said process are granulated in granulator. These granules are added into the lubricant granule, mixed and optionally tablet or pellet forms can be obtained.
  • the formulations of the present invention are preferably prepared by wet granulation method and the formulation obtained is optionally filled into capsules or sachets or can be compressed in tablet form.
  • the tablets can optionally be coated with film coating agents, for instance sugar based coating agents, water soluble film coating agents, enteric coating or modified release coating agents.
  • nateglinide and at least one excipient are granulated and the granules obtained are mixed with at least one other excipient.
  • the formulation obtained is compressed in tablet form and coated with a film coating agent.
  • Saccharose can be used singly or optionally with any of the agents such as talc, calcium carbonate, calcium phosphate, calcium sulphate, gelatine, gum arabic, polyvinylpyrrolidone and pullulan or a combination thereof as the sugar based coating agent.
  • agents such as talc, calcium carbonate, calcium phosphate, calcium sulphate, gelatine, gum arabic, polyvinylpyrrolidone and pullulan or a combination thereof as the sugar based coating agent.
  • the water soluble film coating agent can be selected from cellulose derivatives such as hydroxypropyl cellulose, hydroxypropyl methyl cellulose, hydroxyethyl cellulose, methyl hydroxyethyl cellulose and sodium carboxymethyl cellulose; synthetic polymers such as polyvinyl acetal diethyl aminoacetate, aminoalkyl methacrylate copolymers and polyvinylpyrrolidone and polysaccharides such as pullulan or combinations thereof.
  • cellulose derivatives such as hydroxypropyl cellulose, hydroxypropyl methyl cellulose, hydroxyethyl cellulose, methyl hydroxyethyl cellulose and sodium carboxymethyl cellulose
  • synthetic polymers such as polyvinyl acetal diethyl aminoacetate, aminoalkyl methacrylate copolymers and polyvinylpyrrolidone and polysaccharides such as pullulan or combinations thereof.
  • the enteric coating agents can be selected from cellulose derivatives such as hydroxypropyl methyl cellulose phthalate, hydroxypropyl methyl cellulose acetate succinate, carboxymethyl ethyl cellulose, cellulose acetate phthalate; acrylic acid derivatives such as methacrylic acid copolymer L, methacrylic acid copolymer LD and methacrylic acid copolymer S and natural substances such as shellac or combinations thereof.
  • cellulose derivatives such as hydroxypropyl methyl cellulose phthalate, hydroxypropyl methyl cellulose acetate succinate, carboxymethyl ethyl cellulose, cellulose acetate phthalate
  • acrylic acid derivatives such as methacrylic acid copolymer L, methacrylic acid copolymer LD and methacrylic acid copolymer S and natural substances such as shellac or combinations thereof.
  • the delayed release coating agents can be selected from cellulose derivatives such as ethyl cellulose; acrylic acid derivatives such as aminoalkyl methacrylate copolymer RS, emulsion copolymer of ethyl acrylate-methyl methacrylate or combinations thereof.
  • formulations can be used in the treatment of type 2 diabetes that cannot be controlled by diet and exercise.
  • compositions of the present invention comprising nateglinide can comprise a second active agent in addition to nateglinide.
  • Said second active agent can be selected from a group comprising meglinitides, alpha glucosidase inhibitors, sulfonylureas, tiazolidinediones, biguanides, dipeptidyl peptidase-4 inhibitors.
  • said second active agent can be selected from a group comprising the agents such as repaglinide belonging to meglitinide group; alpha-glucosidase inhibitor acarbose; acetohexamide, glindeklamid, glibornuride, gliclazide, gliquidone, glimepiride, glipizide, chlorpropamide, tolbutamide belonging to sulfonylurea group; pioglitazone, rosiglitazone, rivoglitazone, rosiglitazone maleate, pioglitazone hydrochloride, troglitazone belonging to thiazolidinedione group; phenformin, metformin or a pharmaceutically acceptable salt thereof, for instance metformin hydrochloride belonging to biguanide group; dipeptidyl peptidase-4 inhibitors sitagliptin, vildagliptin, saxagliptin, saxagli
  • nateglinide and the second active agent can be comprised in the same formulation while they can also be prepared in two different formulations. In the case that they are prepared in two different formulations, said formulations can be combined in a single dosage form or they can be in a treatment package form of independent but same or different dosage forms.
  • the formulations comprising the second active agent can be in various dosage forms suitable for oral use, for instance in tablet, film coated tablet, prolonged release tablet, modified release tablet, capsule, dry powder to form suspension, effervescent tablet, effervescent granule, orodispersible tablet, chewable tablet, sachet forms.
  • suitable for oral use for instance in tablet, film coated tablet, prolonged release tablet, modified release tablet, capsule, dry powder to form suspension, effervescent tablet, effervescent granule, orodispersible tablet, chewable tablet, sachet forms.
  • the examples for the formulations of the present invention are given below.
  • Example 1 Formulation and Production Method for Preparation of the Tablets Comprising Nateglinide.
  • Each substance comprised in the formulation given above is measured one by one.
  • Each substance measured is progressively mixed in said formulation obtained by direct compression method.
  • the powder mixture obtained is compressed in tablet compression machine and formed into tablets.
  • Example 2 Formulation for Preparation of Treatment Package Comprising Nateglinide and Metformin.
  • the formulation comprising nateglinide given above is prepared by dry granulation method.
  • the other excipients except from the lubricant in the formulation are mixed by an appropriate method and subjected to precompression process.
  • the tablets obtained after precompression are granulated in granulator. These granules are added into the lubricant granule, mixed together and the tablet form is obtained.
  • the formulation comprising metformin is prepared by wet granulation method and the first is step is mixing the active agent, the effervescent couple and the other excipients.
  • the mixture obtained is subjected to granulation process. After the granules obtained are dried; sieving, adding the other excipients and mixing processes are performed respectively. Tablet compression is performed in the last step and effervescent tablets are obtained.
  • Example 3 Formulation for Preparation of Tablets Comprising Nateglinide and Metformin.
  • the formulation comprising the excipients given above has been prepared by wet granulation method.
  • wet granulation nateglinide and metformin are wet sieved after being granulated with the granulation solution comprising the binder and dried in fluid bed dryer.
  • the mixture obtained is mixed I with the other excipients and homogenized.
  • the lubricant is added in the last step of the mixture.
  • the formulation is formed into tablets after this step.

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  • Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Preparation (AREA)

Abstract

Cette invention concerne des préparations pharmaceutiques comprenant du natéglinide qui sont utilisées pour le traitement du diabète.
PCT/TR2012/000168 2011-11-23 2012-10-04 Préparations à dispersion rapide contenant du natéglinide Ceased WO2013077823A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
TR201111590 2011-11-23
TR2011/11590 2011-11-23
TR201112200 2011-12-09
TR2011/12200 2011-12-09

Publications (1)

Publication Number Publication Date
WO2013077823A1 true WO2013077823A1 (fr) 2013-05-30

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Application Number Title Priority Date Filing Date
PCT/TR2012/000168 Ceased WO2013077823A1 (fr) 2011-11-23 2012-10-04 Préparations à dispersion rapide contenant du natéglinide

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WO (1) WO2013077823A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105534931A (zh) * 2015-12-25 2016-05-04 安徽环球药业股份有限公司 那格列奈片及直接压片法制备那格列奈片的方法
CN108451923A (zh) * 2018-05-31 2018-08-28 常州兰陵制药有限公司 盐酸二甲双胍速释胶囊及其制备方法
CN120643630A (zh) * 2025-08-21 2025-09-16 湖北研妆实业有限公司 一种用于女性卵巢保养组合物及其制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002072146A2 (fr) * 2001-03-12 2002-09-19 Novartis Ag Combinaison de composes organiques
US20030162816A1 (en) * 1999-09-17 2003-08-28 Gatlin Marjorie Regan Method of treating metabolic disorders, especially diabetes, or a disease or condition associated with diabetes
WO2005051360A1 (fr) * 2003-11-28 2005-06-09 Ranbaxy Laboratories Limited Compositions pharmaceutiques comprenant de la nateglinide et un agent tensioactif

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030162816A1 (en) * 1999-09-17 2003-08-28 Gatlin Marjorie Regan Method of treating metabolic disorders, especially diabetes, or a disease or condition associated with diabetes
WO2002072146A2 (fr) * 2001-03-12 2002-09-19 Novartis Ag Combinaison de composes organiques
WO2005051360A1 (fr) * 2003-11-28 2005-06-09 Ranbaxy Laboratories Limited Compositions pharmaceutiques comprenant de la nateglinide et un agent tensioactif

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105534931A (zh) * 2015-12-25 2016-05-04 安徽环球药业股份有限公司 那格列奈片及直接压片法制备那格列奈片的方法
CN108451923A (zh) * 2018-05-31 2018-08-28 常州兰陵制药有限公司 盐酸二甲双胍速释胶囊及其制备方法
CN120643630A (zh) * 2025-08-21 2025-09-16 湖北研妆实业有限公司 一种用于女性卵巢保养组合物及其制备方法

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