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WO1997018814A1 - Formulations pharmaceutiques - Google Patents

Formulations pharmaceutiques Download PDF

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Publication number
WO1997018814A1
WO1997018814A1 PCT/EP1996/005020 EP9605020W WO9718814A1 WO 1997018814 A1 WO1997018814 A1 WO 1997018814A1 EP 9605020 W EP9605020 W EP 9605020W WO 9718814 A1 WO9718814 A1 WO 9718814A1
Authority
WO
WIPO (PCT)
Prior art keywords
formulation
molecular weight
polyethylene oxide
range
low molecular
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/EP1996/005020
Other languages
English (en)
Inventor
Ross James Macrae
Janet Sarah Smith
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pfizer Corp Belgium
Pfizer Ltd Great Britain
Pfizer Research and Development Co NV SA
Pfizer Corp SRL
Original Assignee
Pfizer Corp Belgium
Pfizer Ltd Great Britain
Pfizer Research and Development Co NV SA
Pfizer Corp SRL
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
Priority to KR1019980703777A priority Critical patent/KR19990071505A/ko
Priority to BR9611626A priority patent/BR9611626A/pt
Priority to JP9519364A priority patent/JPH10513481A/ja
Priority to AU75721/96A priority patent/AU709560B2/en
Priority to NZ322053A priority patent/NZ322053A/xx
Priority to EP96938215A priority patent/EP0862437A1/fr
Priority to SK630-98A priority patent/SK63098A3/sk
Priority to PL96326981A priority patent/PL326981A1/xx
Application filed by Pfizer Corp Belgium, Pfizer Ltd Great Britain, Pfizer Research and Development Co NV SA, Pfizer Corp SRL filed Critical Pfizer Corp Belgium
Priority to HU9903734A priority patent/HUP9903734A3/hu
Publication of WO1997018814A1 publication Critical patent/WO1997018814A1/fr
Priority to IS4706A priority patent/IS4706A/is
Priority to BG102438A priority patent/BG102438A/xx
Priority to NO982302A priority patent/NO982302L/no
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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
    • 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
    • A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
    • 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
    • A61K9/2031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers
    • 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

  • This invention relates to controlled-release oral pharmaceutical formulations
  • Controlled-release oral pharmaceutical formulations are known Their purpose is to modify the rate of drug release, for example to produce a constant rate of release of a drug into the gastrointestinal tract of a patient, or to delay the release of a drug into the gastrointestinal tract of a patient (see 'Sustained and Controlled Release Drug Delivery Systems', pp 3-6, edited by J R Robinson, published by Marcel Dekker Inc)
  • US Patent N° 4,765,989 discloses an osmotic delivery device for delivering inter alia nifedipi ⁇ e or doxazosin It has a perforated semipermeable wall enclosing a drug composition which includes an osmopolymer, and a pusher composition containing a second osmopolymer
  • a drug composition which includes an osmopolymer
  • a pusher composition containing a second osmopolymer The performance of this prior art device is satisfactory, but it has the disadvantage that it is very complicated, leading to high manufacturing costs
  • UK Patent Application 2,123,291 discloses a sustained release formulation of suloctidil which is a two-part tablet a first part is a prompt-release portion and a second part is a slow-release portion, which must contain a surface-active agent to promote bio-erosion
  • US Patent N° 5,393,765 discloses an erodibie pharmaceutical composition providing a zero order controlled release profile, comprising low viscosity hydroxypropylmethyl cellulose
  • a controlled-release pharmaceutical formulation for oral administration consisting essentially of an active drug compound low molecular weight polyethylene oxide, hydroxypropylmethyl cellulose tabletting excipients and optionally one or more enteric polymers
  • formulations of the present invention may also be administered buccally (i e placed behind the top lip and allowed to dissolve) and the term includes such formulations "Consisting essentially of means that at least 95% by weight of the formulation is made up of the listed components. At least 99% by weight of uncoated formulations, and the cores of coated formulations, are preferably made up of the listed components.
  • Polymerized ethylene oxide having a number average molecular weight less than 100,000 is sometimes referred to as "polyethylene glycol".
  • polyethylene glycol Polyethylene glycol
  • low molecular weight polyethylene oxide is used to refer to polymerized ethylene oxide in the number average molecular weight range of interest, namely 15,000 to 750,000.
  • Tabletting excipients making up formulations according to the invention may be conven ⁇ tional tabletting excipients, for example dibasic calcium phosphate, lactose and magnesium stearate.
  • the first class is weakly basic compounds. Examples of this class include dipyridamole, noscapine, papaverine, doxazosin, sildenafil and prazosin. Doxazosin and its pharmaceutically acceptable salts are of particular interest.
  • the second class are compounds having high solubility in aqueous media.
  • this class include salbutamol, metoprolol, propanolol, aminophylline, isosorbide mono- and dinitrate, glyceryl trinitrate, verapamil, captopril, diltiazem, morphine, chlorpheni- ramine, promethazine, eletriptan, darifenacin and fluconazole.
  • the third class are compounds having low solubility in aqueous media.
  • Examples of this class include nifedipine, griseofulvin, carbamazepine, felodipine, nimodipine and megestrol.
  • solubility in aqueous media and “low solubility in aqueous media” will be understood by those skilled in the art. However, the former may be defined as a solubility
  • Formulations according to the invention have the advantage that they produce a constant rate of release of drugs that are weakly basic and/or have a high solubility in aqueous media in in vitro models of the gastrointestinal tract, and so are expected to produce a constant rate of release of the drug in the gastrointestinal tract of a patient.
  • the formulations of the invention have the advantage that they produce a delayed or pulsed release of the drug.
  • the formulations are very simple and so can be manufactured at a compara ⁇ tively low cost.
  • the hydroxypropylmethyl cellulose has a number average molecular weight in the range 80,000-250,000.
  • the hydroxypropylmethyl cellulose has a degree of methyl substitution in the range 19-30 %.
  • the hydroxypropylmethyl cellulose has a degree of hydroxy substitution in the range 4-12 %.
  • a number of hydroxypropylme- thyl cellulose polymers are available commercially under the brand name Methocel®, and some of those suitable for use in formulations according to the invention are given in the table below:
  • Methocel® K4M has characteristics of particular interest.
  • the low molecular weight polyethylene oxide has a number average molecular weight in the range 20,000 to 500,000, more preferably 100,000-300,000.
  • Polyethylene oxide with a number average molecular weight above 100,000 is a powder, which makes it easier to handle than lower molecular weight polyethylene oxide, which has a lower melting point.
  • polyethylene oxide with a number average molecular weight of 6000 has a melting point of 60-63°C It will be apparent to those skilled in the art that the polyethylene oxide may consist of molecules of different chain lengths, but that the average chain length gives a molecular weight in the range stated. The same applies to the hydroxypropylmethyl cellulose.
  • Formulations according to the invention may contain an enteric polymer admixed with the other components of the formulation.
  • formulations according to the invention are preferably provided with a coating of an enteric polymer.
  • Enteric polymers that may be mentioned are phthalate derivatives (including cellulose acetate phthalate, polyvinyiacetate phthalate and hydroxypropylmethyl cellulose phthalate), polyacrylic acid derivatives (including methacrylic acid copolymer), and vinyl acetate and crotonic acid copolymers. Methacrylic acid copolymer is of particular interest.
  • the formulation contains up to 50% by weight of active drug compound, for example 1-20%.
  • formulations of the invention contain 5-30% by weight of low molecular weight polyethylene oxide, for example 8-10%.
  • the formulations of the invention contain 10-60% by weight of hydroxypropyl- methyl cellulose, for example 25-35%.
  • Formulations having enteric polymer admixed with the other components of the formula ⁇ tion preferably have 10-40% by weight of admixed enteric polymer, for example 25-35%.
  • the mass ratio of low molecular weight polyethylene oxide:hydroxypropylmethyl cellulose is in the range 2:1- 1 :5.
  • the mass ratio of (low molecular weight polyethylene ox- ide+hydroxypropylmethyl cellulose):admixed enteric polymer is in the range 1 :2-6: 1 , more preferably 1 :2-2:1.
  • the enteric coating (where present) makes up 2-15% by weight of the formulation, more preferably 5-10% by weight of the formulation.
  • the use of low molecular weight polyethylene oxide in an oral controlled-release pharmaceutical formulation having a hydroxypropylmethyl cellulose matrix, to enhance the erosion of the matrix after a predetermined period of time following administration of the formulation to a patient
  • the predetermined period of time is 6 hours In this way, a constant rate of drug release can be achieved in the gastrointestinal tract of a patient despite the varying conditions which exist along its length
  • a process for the production of a pharmaceutical formulation as defined in claim 1 which comprises mixing an active drug compound, low molecular weight polyethylene oxide, hydroxypropylmethyl cellulose, tabletting excipients, and optionally one or more enteric polymers, followed by pressing into tablets
  • formulations according to the present invention may be measured in a model of the gastrointestinal tract such as Apparatus 1 of USP 22, page
  • Figure 1 shows the percentage of drug compound released v time from formulations according to the invention [as prepared in Examples 1 (a) and 1 (b)] in comparison with a control [as prepared in Example 6] using simple dissolution testing
  • Figure 2 shows the percentage of drug compound released v time from a formulation according to the invention [as prepared in Example 2(a)] using dissolution testing with first an acidic and then a neutral dissolution medium
  • Methacrylic acid copolymer type C a 6 500
  • Example 5 Sustained release formulations of fluconazole (suitable for buccal administration.
  • Example 1 The tablets of Examples 1 (a), 1 (b) and 6 were dissolved using Apparatus 1 of USP 22, page 1578, Method 1 (baskets)
  • the dissolution fluid was 900ml of water at 37°C
  • the rotation speed of the baskets was 100 rpm
  • the drug compound released was detected by UV spectroscopy at a wavelength of 246 nm
  • the percentage of drug compound released v time for each tablet type is shown in Figure 1
  • Example 2(a) The tablets of Example 2(a) were dissolved using Apparatus 1 of USP 22, page 1578, Method 1 (baskets)
  • the rotation speed of the baskets was 200 rpm, and the drug compound released was detected by UV spectros- copy at a wavelength of 246 nm
  • the percentage of drug compound released v time is shown in Figure 2

Landscapes

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

Abstract

L'invention concerne une formulation pharmaceutique à libération prolongée, destinée à une administration par voie orale et comprenant essentiellement un composé médicamenteux actif, un oxyde de polyéthylène à bas poids moléculaire, une cellulose d'hydroxypropylméthyle, des excipients de fabrication de comprimés, et éventuellement un ou plusieurs polymères entérosolubles. Avec des formulations selon l'invention, on obtient un taux constant de libération de médicament dans des modèles in vitro du tractus gastro-intestinal.
PCT/EP1996/005020 1995-11-21 1996-11-11 Formulations pharmaceutiques Ceased WO1997018814A1 (fr)

Priority Applications (12)

Application Number Priority Date Filing Date Title
SK630-98A SK63098A3 (en) 1995-11-21 1996-11-11 Controlled-release pharmaceutical formulation, process for its preparation and use of polyethyleneoxide
JP9519364A JPH10513481A (ja) 1995-11-21 1996-11-11 医薬製剤
AU75721/96A AU709560B2 (en) 1995-11-21 1996-11-11 Pharmaceutical formulations
NZ322053A NZ322053A (en) 1995-11-21 1996-11-11 Controlled release pharmaceutical formulation comprising an active, a low MW polyethylene oxide, HPMC and one or more enteric polymers
EP96938215A EP0862437A1 (fr) 1995-11-21 1996-11-11 Formulations pharmaceutiques
PL96326981A PL326981A1 (en) 1995-11-21 1996-11-11 Pharmaceutic preparations
HU9903734A HUP9903734A3 (en) 1995-11-21 1996-11-11 Controlled-release pharmaceutical formulations for oral administration and method for preparing this
KR1019980703777A KR19990071505A (ko) 1995-11-21 1996-11-11 약학 제제
BR9611626A BR9611626A (pt) 1995-11-21 1996-11-11 Formulações farmacéuticas
IS4706A IS4706A (is) 1995-11-21 1998-03-31 Lyfjasamsetningar
BG102438A BG102438A (en) 1995-11-21 1998-05-08 Medicamentous form
NO982302A NO982302L (no) 1995-11-21 1998-05-20 Farmas°ytisk sammensetning

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9523752.5 1995-11-21
GBGB9523752.5A GB9523752D0 (en) 1995-11-21 1995-11-21 Pharmaceutical formulations

Publications (1)

Publication Number Publication Date
WO1997018814A1 true WO1997018814A1 (fr) 1997-05-29

Family

ID=10784188

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1996/005020 Ceased WO1997018814A1 (fr) 1995-11-21 1996-11-11 Formulations pharmaceutiques

Country Status (29)

Country Link
EP (1) EP0862437A1 (fr)
JP (1) JPH10513481A (fr)
KR (1) KR19990071505A (fr)
CN (1) CN1215993A (fr)
AP (1) AP718A (fr)
AR (1) AR004335A1 (fr)
AU (1) AU709560B2 (fr)
BG (1) BG102438A (fr)
BR (1) BR9611626A (fr)
CA (1) CA2232715A1 (fr)
CO (1) CO4480020A1 (fr)
CZ (1) CZ155498A3 (fr)
GB (1) GB9523752D0 (fr)
HR (1) HRP960554A2 (fr)
HU (1) HUP9903734A3 (fr)
IS (1) IS4706A (fr)
MA (1) MA26410A1 (fr)
MX (1) MX9804008A (fr)
NO (1) NO982302L (fr)
NZ (1) NZ322053A (fr)
OA (1) OA10687A (fr)
PE (1) PE22898A1 (fr)
PL (1) PL326981A1 (fr)
SK (1) SK63098A3 (fr)
TN (1) TNSN96141A1 (fr)
TR (1) TR199800902T2 (fr)
WO (1) WO1997018814A1 (fr)
YU (1) YU62096A (fr)
ZA (1) ZA969722B (fr)

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EP0910349A2 (fr) * 1996-06-21 1999-04-28 Temple University - Of The Commonwealth System Of Higher Education Comprime a liberation controlee
WO1999030697A3 (fr) * 1997-12-16 1999-08-26 Pfizer Prod Inc Composition efficace pour le traitement de l'impuissance
EP0960621A3 (fr) * 1998-05-15 2000-01-05 Pfizer Inc. Compositions pharmaceutiques comprenant du sildenafil
EP0974343A1 (fr) * 1998-07-22 2000-01-26 Pharma Pass LLC Composition contenant du metoprolol et procédé de préparation
EP0987020A1 (fr) * 1998-09-04 2000-03-22 Pharma Pass LLC Composition contenant du metoprolol et procédé de préparation
WO2000024383A1 (fr) * 1998-10-23 2000-05-04 Pfizer Research And Development Company, N.V./S.A. Formulations pharmaceutiques a liberation controlee contenant un inhibiteur de pde-5 de cgmp
US6475521B1 (en) 1998-03-19 2002-11-05 Bristol-Myers Squibb Co. Biphasic controlled release delivery system for high solubility pharmaceuticals and method
EP1293196A3 (fr) * 2001-09-14 2004-01-02 Pharma Pass II LLC Composition pharmaceutique comprenant de la doxazosine
US6723340B2 (en) 2001-10-25 2004-04-20 Depomed, Inc. Optimal polymer mixtures for gastric retentive tablets
WO2005037247A3 (fr) * 2003-10-17 2005-06-30 Ranbaxy Lab Ltd Formulations matricielles de doxazosine a administration orale
WO2005107702A3 (fr) * 2004-05-11 2006-10-05 Glenmark Pharmaceuticals Ltd Compositions pharmaceutiques vaginales mucoadhesives a liberation prolongee
JP2006298945A (ja) * 1998-10-14 2006-11-02 Novartis Ag 徐放性医薬組成物および薬学的活性剤の放出の方法
WO2010071320A2 (fr) 2008-12-17 2010-06-24 동아제약 주식회사 Composition à libération contrôlée pour produire une préparation à libération prolongée contenant de l'udénafil
US7759368B2 (en) * 2004-05-28 2010-07-20 Hanmi Pharm. Co., Ltd Sustained release composition for oral administration of niacin
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HUP9903734A3 (en) 2000-04-28
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BG102438A (en) 1999-01-29
CO4480020A1 (es) 1997-07-09
AP9600883A0 (en) 1997-01-31
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AR004335A1 (es) 1998-11-04
AU7572196A (en) 1997-06-11
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BR9611626A (pt) 1999-06-01
JPH10513481A (ja) 1998-12-22
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GB9523752D0 (en) 1996-01-24
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OA10687A (en) 2002-11-27

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