WO2002072069A1 - Nouveaux comprimes et gelules et procede de preparation correspondant - Google Patents

Nouveaux comprimes et gelules et procede de preparation correspondant Download PDF

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Publication number
WO2002072069A1
WO2002072069A1 PCT/DK2002/000163 DK0200163W WO02072069A1 WO 2002072069 A1 WO2002072069 A1 WO 2002072069A1 DK 0200163 W DK0200163 W DK 0200163W WO 02072069 A1 WO02072069 A1 WO 02072069A1
Authority
WO
WIPO (PCT)
Prior art keywords
tablet
weight
capsule
active ingredient
microcrystalline cellulose
Prior art date
Application number
PCT/DK2002/000163
Other languages
English (en)
Inventor
Thyge Borup Hjorth
Breian Knudsen
Original Assignee
Novo Nordisk A/S
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Novo Nordisk A/S filed Critical Novo Nordisk A/S
Priority to EP02702234A priority Critical patent/EP1370244A1/fr
Publication of WO2002072069A1 publication Critical patent/WO2002072069A1/fr

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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
    • 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4841—Filling excipients; Inactive ingredients
    • A61K9/485—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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4841—Filling excipients; Inactive ingredients
    • A61K9/4866—Organic macromolecular compounds

Definitions

  • Novel tablets and capsules and a process for its preparation Novel tablets and capsules and a process for its preparation.
  • the present invention relates to novel tablets and capsules with relatively low amounts of the active ingredient.
  • the present invention further relates to tablets and capsules comprising as the active ingredient (-) 3-[4-[2-(phenoxazin-10-yl) ethoxy]phenyl]-2-ethoxypropanoic acid or a pharmaceutically acceptable salt thereof.
  • (2S)(-)-3-[4-[2-(phenoxazin-10-yl) ethoxy]phenyl]-2-ethoxypropanoic acid in the following (-) 3-[4-[2-(phenoxazin-10-yl)ethoxy]phenyl]-2-ethoxypropanoic acid) and pharmaceutically ac- ceptable salts thereof has been found useful in the treatment of type 2 diabetes acting as an insulin sensitizer as disclosed in eg PCT Publication WO 99/19313, WO 00/50414 and WO 00/63192, which are incorporated herein by reference.
  • compositions containing (-) 3-[4-[2-(phenoxazin-10-yl)ethoxy]phenyl]-2-ethoxypropanoic acid as active ingredient or a pharmaceutically acceptable salt thereof are described in WO01/74363.
  • One object of the present invention is to provide tablets and capsules having improved homogeneity.
  • Another object of the present invention is to provide tablets and capsules having improved homogeneity with respect to the content of active ingredient. Another object of the present invention is to provide tablets and capsules having improved homogeneity with respect to the distribution of active ingredient.
  • Another object of the present invention is to provide tablets and capsules having a low content of active ingredient.
  • a still further object of the present invention is to provide tablets and capsules being supe- rior to the known art.
  • a tablet or capsule wherein the content of active ingredient in the tablet or capsule is between about 3 % (weight/weight) and about 0.001 % (weight/weight) can be prepared with improved homogenous distribution of the active ingredient if microcrystalline cellulose and silicon dioxide are used as some of the starting materials.
  • a tablet or capsule wherein the content of active ingredient in the tablet or capsule is not more than about 2 % (weight/weight) can be prepared with improved homogenous distribution of the active ingredient if microcrystalline cellulose and silicon dioxide are used as some of the starting materials.
  • any sort of microcrystalline cellulose can be used for the preparation of the tablets and capsules according to the present invention.
  • the microcrystalline cellulose used for the preparation of the tablets and capsules according to the present invention has a bulk density above 0.35 g/ml.
  • the microcrystalline cellulose used for the preparation of the tablets and capsules according to the present invention has a particle size above about 50 micrometer.
  • a tablet or capsule according to the present invention comprises preferably microcrystalline cellulose in an amount of at least 20 %, more preferred of at least 30 % and even more preferred of at least 40 % (weight/weight) and most preferred in an amount of at least 45% (weight/weight).
  • the tablet or capsule according to the invention comprises microcrystalline cellulose in amounts ranging from 20% to 80% (weight/weight) , amounts from 30% to 70% are preferred while amounts from 40% to 60% are even more preferred and amounts ranging from 45% to 55% are especially preferred.
  • any sort of silicone dioxide can be used for the preparation of the tablets and cap- sules according to the present invention.
  • the silicone dioxide used for the preparation of the tablets and capsules according to the present invention has a particle size from about 1 namometer to about 100 micrometer.
  • a tablet or capsule according to the present invention comprises preferably an amount of silicone dioxide in the range from 0.1 to 5 %, preferably in the range from 0.2% to 3%, even more preferred in the range from 0.5% to 1 ,5% (weight/weight).
  • the tablet or capsule further comprises mannitol.
  • the tablet or capsule comprises mannitol in an amount of at least 20%, preferably at least 30% an even more pre- ferred at lest 40% (weight/weight) and most preferred in an amount of at least 45%
  • the tablet or capsule comprises mannitol in amounts ranging from 20% to 80% (weight/weight) , amounts from 30% to 70%) are preferred while amounts from 40% to 60% are even more preferred and amounts ranging from 45% to 55% are especially preferred.
  • the tablet or capsule comprises mannitol and microcrystalline cellulose in proportions between 2:8 and 8:2, preferably between 3:5 and 5:3, more preferred between 4:6 and 6:4, and even more preferred between 45:55 and 55:45.
  • the tablet or capsule comprises talc in the range from 0.1 to 10 % (weight/weight).
  • the tablet or capsule comprises micro- crystalline cellulose in an amount ranging from 45% to 55% and silicon dioxide in an amount from 0,5%) to 1 ,5%(weight/weight).
  • the tablet or capsule comprises: (i) an active ingredient selected from the group consisting of (-) 3-[4-[2-(phenoxazin-10-yl) ethoxy]phenyl]-2- ethoxypropanoic acid, pharmaceutically acceptable salt, ester, metabolite, hydrate, solvate, polymorph, and pro-drug form thereof, (ii) microcrystalline cellulose; and (iii) silicon dioxide, wherein the amount of said active ingredient is between about 0.01% and about 2,0% (weight/weight); the amount of said microcrystalline cellulose is between about 40% and about 50%) (weight/weight); and the amount of said silicone dioxide is between about 0.8% and about 1.2% (weight/weight).
  • an active ingredient selected from the group consisting of (-) 3-[4-[2-(phenoxazin-10-yl) ethoxy]phenyl]-2- ethoxypropanoic acid, pharmaceutically acceptable salt, ester, metabolite, hydrate, solvate, polymorph, and pro-d
  • Non-limiting examples of a formulation according to invention include the following (expressed as % weight/ total weight of each ingredient):
  • the tablets or capsules are prepared using one of the commercial products marketed under the designations ProSolv HD 90, Pro- Solv SMCC 50, and ProSolv SMCC 90 by the firm PenWest, each of which contain both microcrystalline cellulose and silicon dioxide.
  • the tablets or capsules have a relative standard deviation (RSD) for the content of active ingredient in the tablet or capsule which is not more than about 4%.
  • RSD relative standard deviation
  • the RSD value is not more than about 3 %, more preferred the RSD value is not more than about 2,5 %, and even more preferred the RSD value is not more than about 2 %, especially preferred the RSD value is not more than about 1 ,5 %, and even more preferred the RSD value is not more than about 1 %.
  • the relative standard deviation (RSD) for the content of active ingredient in the tablets of the present invention can be determined as described in the United States Pharmacopeia (USP 24) 2000, chapter 905 using the test for Uniformity of Dosage Units, ⁇ 905>, USP XV.
  • the bulk and tapped density can be determined as described in method BTD-8, Handbook of Pharmaceutical Excipients, 2nd ed., 1994. Particle size distribution can be determined by Sieve analysis using US standard sieves.
  • the tablets and capsules according to the present invention can be prepared in a manner known perse. More specifically, the tablets and capsules may be prepared by conventional techniques, e.g. as described in Remington: The Science and Practise of Pharmacy, 19 th edition, 1995. According to a preferred feature of the present invention, the tablet or capsule ac- cording to the present invention are prepared by direct compression. Direct compression has the advantage that it is possible to first mix all the ingredients which are to be present in the final tablet or capsule and then to subject the mixture to direct compression.
  • the active ingredient present in the tablets and capsules of the present invention can be any pharmaceutical such as analgesics and anti-inflammatory agents, anthelminthics, anti- arrhythmic agents, antibacterial agents, anticoaglants, antidepressants, antidiabetic agents, antiepileptics, antifungal agents, antigout agents, antihypertensive agents, antimalarials, an- timigraine gents, antimuscarinic agents, antineoplastic agents, immunosuppressants, anti- protozoal agents, antithyroid agents, antiviral agents, anxiolytic sedatives, hypnotics, neuro- leptics, beta-adrenoceptor blocking agents, calcium regulating agents, cardiac inotropic agents, chelating agents, antidotes, antagonists, corticosteroids, diuretics, dopaminergic an- tiparkinsonian agents, gastro-intestinal agents, anaesthetics, hormones, lipid regulating agents, , anti
  • An example of a specific medicaments is (-) 3-[4-[2-(phenoxazin-10-yl)ethoxy]phenyl]-2- ethoxypropanoic acid and pharmaceutically acceptable salts thereof.
  • Pharmaceutically acceptable salts forming part of this invention include salts such as alkali metal salts like Li, Na, and K salts, alkaline earth metal salts like Ca and Mg salts, salts of organic bases such as lysine, arginine, guanidine, diethanolamine, choline and the like, ammonium or substituted ammonium salts, aluminium salts.
  • Salts may include acid addition salts where appropriate which are, sulphates, nitrates, phosphates, perchlorates, borates, hydrohalides, acetates, tartrates, maleates, citrates, succinates, palmoates, methanesulplionates, benzoates, salicy- lates, hydroxynaphthoates, benzenesulfonates, ascorbates, glycerophosphates, ketogluta- rates and the like.
  • Further examples of pharmaceutically acceptable inorganic or organic acid addition salts include the pharmaceutically acceptable salts listed in J. Pharm. Sci. 1977, 66, 2, which is incorporated herein by reference.
  • the present invention also encompasses esters, metabolites, hydrates, solvates, poly- morphs, and pro-drug forms of (-) 3-[4-[2-(phenoxazin-10-yl)ethoxy]phenyl]-2- ethoxypropanoic acid.
  • (-) 3-[4-[2-(phenoxazin-10-yl)ethoxy]phenyl]-2-ethoxypropanoic acid, arginine is used in the present invention.
  • Another example of a specific medicament is 5-[[4-[3-Methyl-4-oxo-3,4-dihydro-2- quinazolinyl]methoxy]phenyl-methyl]thiazolidine-2,4-dione and pharmaceutically acceptable salts thereof as active ingredient as described in PCT Publication WO 97/41097.
  • the present invention also encompasses esters, metabolites, hydrates, solvates, polymorphs, and pro- drug forms of 5-[[4-[3-Methyl-4-oxo-3,4-dihydro-2-quinazolinyl]methoxy]phenyl- methyl]thiazolidine-2,4-dione.
  • suitable carriers present in the tablets and capsules according to the present invention are water, salt solutions, alcohols, polyethylene glycols, polyhydroxyethoxylated castor oil, peanut oil, olive oil, gelatine, lactose, terra alba, sucrose, mannitol, sorbitol, cyclodextrin, amylose, magnesium stearate, talc, gelatin, agar, pectin, acacia, stearic acid or lower alkyl ethers of cellulose, silicic acid, fatty acids, fatty acid amines, fatty acid monoglycerides and diglycerides, pentaerythritol fatty acid esters, polyoxyethylene, hydroxymethylcellulose and polyvinylpyrrolidone.
  • the carrier or diluent may include any sustained release material known in the art, such as glyceryl monostearate or glyceryl distearate, alone or mixed with a wax.
  • the tablets and capsules may also include wetting agents, emulsifying and suspending agents, preserving agents, sweetening agents or flavouring agents.
  • the tablets and capsules of the invention may be formulated so as to provide quick, sustained, or delayed release of the active ingredient after administration to the patient by employing procedures well known in the art.
  • the tablets and capsules can be sterilized and mixed, if desired, with auxiliary agents, emul- sifiers, salt for influencing osmotic pressure, buffers and/or colouring substances and the like, which do not deleteriously react with the active compounds.
  • the preparation may be tabletted, placed in a hard gelatin capsule in powder or pellet form or it can be in the form of a troche or lozenge.
  • Tablets, dragees, or capsules having talc and/or a carbohydrate carrier or binder or the like are particularly suitable for oral application.
  • Preferable carriers for tablets, dragees, or capsules include lactose, corn starch, and/or potato starch.
  • the tablets and capsules of the invention may be administered to a mammal, especially a human in need of such treatment, prevention, elimination, alleviation or amelioration of various diseases as mentioned above.
  • mammals include also animals, both domestic animals, e.g. household pets, and non-domestic animals such as wildlife.
  • the exact dosage of the tablets and capsules will depend upon the mode of administration, on the therapy desired, form in which administered, the subject to be treated and the body weight of the subject to be treated, and the preference and experience of the physician or veterinarian in charge.
  • the powder mixture is compressed into tablets on a tabletting machine.
  • the tablet weight is EXAMPLE 6
  • the powder mixture is compressed into tablets on a tabletting machine.
  • the tablet weight is EXAMPLE 8
  • the powder mixture is compressed into tablets on a tabletting machine.
  • the tablet weight is 110 mg.
  • the powder mixture is compressed into tablets on a tabletting machine.
  • the tablet weight is 110 mg.

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

Abstract

L'invention concerne des comprimés et des gélules dans lesquelles le contenu en principe actif n'est pas supérieur à environ 3 % (poids/poids) pouvant être préparée si la cellulose microcristalline et le dioxyde de silicium sont utilisés comme des produits de départ.
PCT/DK2002/000163 2001-03-12 2002-03-12 Nouveaux comprimes et gelules et procede de preparation correspondant WO2002072069A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP02702234A EP1370244A1 (fr) 2001-03-12 2002-03-12 Nouveaux comprimes et gelules et procede de preparation correspondant

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DKPA200100413 2001-03-12
DKPA200100413 2001-03-12

Publications (1)

Publication Number Publication Date
WO2002072069A1 true WO2002072069A1 (fr) 2002-09-19

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Application Number Title Priority Date Filing Date
PCT/DK2002/000163 WO2002072069A1 (fr) 2001-03-12 2002-03-12 Nouveaux comprimes et gelules et procede de preparation correspondant

Country Status (2)

Country Link
EP (1) EP1370244A1 (fr)
WO (1) WO2002072069A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005000299A1 (fr) * 2003-06-27 2005-01-06 Dr. Reddy's Research Foundation Compositions comprenant de la balaglitazone et d'autres composes antidiabetiques
WO2016033094A1 (fr) * 2014-08-25 2016-03-03 Aimmune Therapeutics, Inc. Formulations de protéines d'oeuf et leurs procédés de fabrication

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2055575A (en) * 1979-07-26 1981-03-11 American Cyanamid Co Palatable anthelmintic tablets for companion animals
EP0638310A1 (fr) * 1993-08-02 1995-02-15 Bristol-Myers Squibb Company Compositions pharmaceutiques à base d'ifétroban
WO1996030016A2 (fr) * 1995-03-28 1996-10-03 Janssen Pharmaceutica N.V. Formulations de ridogrel a petites doses et leur utilisation dans le traitement de maladies intestinales inflammatoires
WO1999046245A2 (fr) * 1998-03-13 1999-09-16 Aventis Pharmaceuticals Inc. PROCEDES DE PREPARATION DE (R)-α- (2,3-DIMETHOXYPHENYL)- 1-[2-(4- FLUOROPHENYL)ETHYL]- 4-PIPERIDINEMETHANOL
WO2001074363A1 (fr) * 2000-04-04 2001-10-11 Novo Nordisk A/S Composition pharmaceutique contenant de l'acide 3-[4[2-phenoxazin-10-yl)ethoxy]phenyl]-2-ethoxypropanoique
WO2002028364A2 (fr) * 2000-10-03 2002-04-11 Sigmapharm, Inc. Stabilisation de formulations de medicaments thyroidiens solides

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2055575A (en) * 1979-07-26 1981-03-11 American Cyanamid Co Palatable anthelmintic tablets for companion animals
EP0638310A1 (fr) * 1993-08-02 1995-02-15 Bristol-Myers Squibb Company Compositions pharmaceutiques à base d'ifétroban
WO1996030016A2 (fr) * 1995-03-28 1996-10-03 Janssen Pharmaceutica N.V. Formulations de ridogrel a petites doses et leur utilisation dans le traitement de maladies intestinales inflammatoires
WO1999046245A2 (fr) * 1998-03-13 1999-09-16 Aventis Pharmaceuticals Inc. PROCEDES DE PREPARATION DE (R)-α- (2,3-DIMETHOXYPHENYL)- 1-[2-(4- FLUOROPHENYL)ETHYL]- 4-PIPERIDINEMETHANOL
WO2001074363A1 (fr) * 2000-04-04 2001-10-11 Novo Nordisk A/S Composition pharmaceutique contenant de l'acide 3-[4[2-phenoxazin-10-yl)ethoxy]phenyl]-2-ethoxypropanoique
WO2002028364A2 (fr) * 2000-10-03 2002-04-11 Sigmapharm, Inc. Stabilisation de formulations de medicaments thyroidiens solides

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
DATABASE STN INTERNATIONAL [online] NÜRNBERG E ET AL: "Coating of cellulose products with highly dispersed silicic acid. Investigations on the improvement of tabletting properties demonstrated in low dose tablets.", XP002902514, retrieved from HCA accession no. 123:237711 *
NÜRNBERG E ET AL: "Coating of cellulose products with colloidal silicon dioxide.", DRUGS MADE IN GERMANY, vol. 39, no. 3, 1996, pages 104 - 107, XP002902513 *
PHARM. IND., vol. 57, no. 3, 1995, pages 252 - 256 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005000299A1 (fr) * 2003-06-27 2005-01-06 Dr. Reddy's Research Foundation Compositions comprenant de la balaglitazone et d'autres composes antidiabetiques
WO2016033094A1 (fr) * 2014-08-25 2016-03-03 Aimmune Therapeutics, Inc. Formulations de protéines d'oeuf et leurs procédés de fabrication
CN106535931A (zh) * 2014-08-25 2017-03-22 艾慕恩治疗公司 卵蛋白制剂及其制备方法
US10918676B2 (en) 2014-08-25 2021-02-16 Aimmune Therapeutics, Inc. Egg protein formulations and methods of manufacture thereof
US11197896B2 (en) 2014-08-25 2021-12-14 Société des Produits Nestlé S.A. Egg protein formulations and methods of manufacture thereof

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Publication number Publication date
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