EP1983967A2 - Composition pharmaceutique contenant de l'irbesartan à libération rapide - Google Patents

Composition pharmaceutique contenant de l'irbesartan à libération rapide

Info

Publication number
EP1983967A2
EP1983967A2 EP07711196A EP07711196A EP1983967A2 EP 1983967 A2 EP1983967 A2 EP 1983967A2 EP 07711196 A EP07711196 A EP 07711196A EP 07711196 A EP07711196 A EP 07711196A EP 1983967 A2 EP1983967 A2 EP 1983967A2
Authority
EP
European Patent Office
Prior art keywords
pharmaceutical composition
tablet
irbesartan
composition according
weight
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.)
Withdrawn
Application number
EP07711196A
Other languages
German (de)
English (en)
Inventor
Julia Schulze Nahrup
Sandra BRÜCK
Rainer Alles
Peter Kraass
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.)
Ratiopharm GmbH
Original Assignee
Ratiopharm GmbH
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 Ratiopharm GmbH filed Critical Ratiopharm GmbH
Publication of EP1983967A2 publication Critical patent/EP1983967A2/fr
Withdrawn legal-status Critical Current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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives

Definitions

  • the present invention relates to a fast-release irbesartan-containing pharmaceutical composition, in particular a fast-release irbesartan-containing tablet.
  • Irbesartan 2-n-butyl-4-spirocyclopentane-1 - [(2 '- (tetra-2-ol-5-yl) biphenyl-4-yl) methyl] -2-imidazolin-5-one is a known angiotensin II antagonist , It is used in particular for cardiovascular problems such as high blood pressure and heart failure, as well as in central nervous system disorders and in the treatment of glaucoma, diabetic retinopathy and renal insufficiency.
  • Irbesartan having the following structure (I)
  • WO-A-91/14679 discloses irbesartan for use in the treatment of hypertension and heart failure.
  • Irbesartan can exist in several polymorphic forms.
  • the polymorphic forms A and B are described in EP 0 708 103 and DE 695 19 788, respectively.
  • WO 03/050110 discloses an amorphous form of irbesartan.
  • Irbesartan has acceptable oral bioavailability, but an unpleasant taste, which renders it unfavorable to administer it in dissolved form, such as in the form of a syrup.
  • a preferred mode of administration is therefore a tablet containing a substantial amount of irbesartan as the active ingredient.
  • the dissolution profile of the tablet is a critical parameter. The tablet should ensure rapid and complete release of the active ingredient. In particular, the dissolution profile should not deteriorate even during long storage times of the tablet, that is, the active ingredient should be released very quickly in the resolution even after storage.
  • EP-A 747 050 describes the difficulties in producing a rapid release irbesartan tablet. According to this document, the tablet should show such a solution behavior that 80% or more of the irbesartan present in the tablet or a salt thereof dissolves within 30 minutes.
  • EP-A 747 050 considers it necessary to formulate the lsbesartan with a surfactant, in particular a poloxamer, into a tablet.
  • a surfactant limits the freedom of the galenic and it would be advantageous to have a rapid release irbesartan tablet that does not necessarily contain a surfactant.
  • the tablets prepared according to EP 747 050 are still capable of improvement, since the release of Irbesartans from these tablets deteriorates when the tablet is stored.
  • EP-A 747050 is currently a rapid release irbesartan tablet called APROVEL ® on the market.
  • APROVEL ® a rapid release irbesartan tablet
  • This product shows a rapid release, however, even in this current market product, the release (ie the release slows down) worsens after storage of the tablets, which is undesirable.
  • the object of the present invention is thus to provide a pharmaceutical composition, in particular a tablet, with high content of lrbesartan, which enables a rapid release of Irbesartans and does not show the problems of the tablets of the prior art.
  • the object is to provide an irbesartan-containing tablet which, even after prolonged storage periods, still allows a rapid release of the active ingredient, such as lrbesartan, allows and in which the release profile changes as little as possible by the storage.
  • a pharmaceutical composition in particular a tablet, with a special mixture of disintegrants solves this problem.
  • the present invention thus relates to a pharmaceutical composition, in particular a tablet, which contains from 20 to 90% by weight, in particular from 50 to 90% by weight, preferably from 60 to 85% by weight, in particular from 60 to 80% by weight preferably 60 to 70 wt .-%, for example about 65% by weight irbesartan or a pharmaceutically acceptable salt thereof and at least 5%, preferably at least 10%, more preferably at least 15%, more preferably at least 20%, by weight, such as at least 25% by weight.
  • Disintegrating agent wherein at least 40 wt.%, Preferably at least 50 wt.%, In particular about 60 wt.% Or more, more preferably about 70 wt.%, Most preferably about 80 wt More of the disintegrant is low-substituted hydroxypropyl cellulose.
  • the irbesartan may be in any polymorphic or amorphous form or in a mixture of such forms, in particular in the polymorphic form A or the polymorphic form B or a mixture thereof, optionally also in admixture with the amorphous form.
  • Particularly preferred is the irbesartan in the polymorphic form A (as described in EP 708 103 and DE 695 19 788).
  • the irbesartan may optionally be present in admixture with a diuretic, as described, for example, in EP-A 1 275 391, in particular with hydrochlorothiazide. If such a diuretic is present in the pharmaceutical composition of the present invention, it is preferably present in an amount of 2 to 33% by weight. In this case, the amount of irbesartan is preferably 20 to 70% by weight, more preferably about 50% by weight, the total amount of the active ingredient combination being not more than 90% by weight, more preferably not more than 85% by weight of the pharmaceutical composition.
  • the proportion of the low-substituted hydroxypropyl cellulose in the disintegrant is not more than 95 wt .-%, preferably not more than 90 wt .-%, in particular not more than 85 wt .-%.
  • the disintegrant of the pharmaceutical composition is therefore preferably 40 to 95%, more preferably 50 to 90%, even more preferably 60 to 90%, especially 70 to 90% by weight, especially 80 to 90% by weight.
  • low-substituted hydroxypropyl cellulose, the remainder of the disintegrant being one or more other disintegrants other than low-substituted hydroxypropyl cellulose.
  • a typical ratio is about 84% low-substituted hydroxypropyl cellulose and about 16% more disintegrant.
  • Preferred low-substituted hydroxypropyl celluloses are available, for example, from Shin Etsu under the name L-HPC.
  • the hydroxypropyl content of the low-substituted hydroxypropylcellulose is generally in the range of 5 to 16%, preferably from 8 to 15%, especially from 10.0 to 12.9%.
  • the hydroxypropyl content is about 10.0 to 12.9%.
  • low-substituted hydroxypropylcellulose may be to the USP (National Formulary) and in particular to the entry under the keyword L-HPC in the standard reference book Fiedler, Lexicon of Auxiliaries for Pharmacy, Cosmetics and adjacent areas, 5th edition 2002 and the brochures Shin Etsu or the American Pharmaceutical Association Arthur H. Kibbe's Handbook of Excipients, 3rd Edition 2000.
  • Low-substituted hydroxypropyl cellulose is used both as a binder and as a disintegrant, as described, for example, in Schmidt ⁇ Christin, active ingredients and excipients for formulation, De Stammur and large-scale production, Stuttgart 1999.
  • low-substituted hydroxypropyl cellulose is one of the disintegrants, not the binders.
  • the low-substituted hydroxypropyl cellulose L-HPC is marketed, for example, under the type designations LH-11, LH-20, LH-21, LH-22, LH-30, LH-31 and LH-32.
  • the types LH-11 and LH-21, especially LH-21 is preferred.
  • Preferred are the low-substituted hydroxypropylcelluloses having small and medium particle sizes, preferably in the range from 30 to 100 .mu.m, more preferably from 30 to 60 .mu.m, in particular from 40 to 50 .mu.m, such as L-HPC LH-11 (about 50 .mu.m) and L-HPC.
  • HPC LH-21 (about 40 microns) used.
  • a variety of low-substituted hydroxypropylcelluloses or a mixture of different low-substituted hydroxypropylcelluloses can be used.
  • the content of low-substituted hydroxypropylcellulose in the drug is usually 4 to 30%, preferably 6 to 27%, more preferably 10 to 25% or 15 to 25% (each based on the total weight of the drug). Also contents of 6 to 14% and 10 to 12% (in each case based on the total weight of the medicament) are preferred.
  • the medicament according to the invention generally also has at least one further disintegrant, specifically preferably at least 5%, in particular at least 10%, more preferably at least 15%, based on the total weight of the disintegrating agents present.
  • the content of further disintegrant (ie, disintegrant which is not low-substituted hydroxypropyl cellulose) in the drug is 1 to 6%, more preferably 1.5 to 5.5%, especially 2 to 5% or 3 to 5% or 4 to 5 % (in each case based on the total weight of the drug).
  • the other disintegrants are not particularly limited, for this purpose, the usual, known in the art disintegrants can be used. Preference is given to the disintegrants which are listed in the already cited standard work by Fiedler under the heading "tablet disintegrants”.
  • Preferred further disintegrants are alginic acid, sodium alginate, cellulose derivatives such as sodium carboxymethyl cellulose and sodium cross carmellose, crospovidone, pregelatinized starch, sodium starch glycolate or starch. Most preferred are the disintegrating agents known as "Super Disintegrants", and especially sodium carboxymethylcellulose and sodium crosscarmellose.
  • disintegrants are also used as binders. Unless an agent specifically assigned to a group in this application serves both as a disintegrating agent can also be used as a binder, it counts according to the invention to the disintegrants and not to the binders, unless otherwise stated or apparent due to the circumstances.
  • composition according to the invention may comprise further customary additives and auxiliaries and, if appropriate, coating agents which are known to the person skilled in the art, and in this respect it is possible, for example. be referred back to the standard reference book by Fiedler or the "Handbook of Excipients".
  • the irbesartan-containing pharmaceutical composition may comprise one or more fillers, binders, flow control agents, lubricants or surfactants, in particular 0 to 20 wt% filler, 0 to 5 wt% binder, 0 to 3 wt% flow control agent , 0 to 2% by weight of lubricant and 0 to 2% by weight of surfactant.
  • the other customary additives and auxiliaries and optionally coating agents are present in a total amount, so that the pharmaceutical composition according to the invention gives 100%.
  • filler one or more compounds which are part of the material to achieve the required total tablet mass can be used.
  • Preferred fillers are inorganic phosphates, such as dibasic calcium phosphate, or sugars or sugar-like substances and their derivatives, in particular lactose, such as lactose monohydrate or anhydrous lactose, dextrose, sorbitol, mannitol, sucrose, maltodextrin, isomalt and tablettose.
  • lactose such as lactose monohydrate or anhydrous lactose
  • dextrose sorbitol
  • mannitol mannitol
  • sucrose maltodextrin
  • isomalt and tablettose.
  • Cellulose such as microcrystalline cellulose or powdered cellulose also belong to the fillers according to the invention.
  • the pharmaceutical composition according to the invention contains no fillers.
  • the binder is one or more compounds that permit granulation of the irbesartan and / or other ingredients into larger, denser particles.
  • Preferred binders are gelatin, povidone (an N-vinylpyrrolidone polymer), hydroxypropylmethylcellulose, and especially copovidone (a copolymer of N-vinyl-2-pyrrolidone and vinyl acetate, e.g., Piasdon S-630 or Kollidon VA64).
  • the flow control agent is one or more compounds having the flow properties of the pharmaceutical Improve composition.
  • Preferred flow control agents are silica or magnesium trisilicate, eg Aerosil Type 200, or talc.
  • the lubricant used is one or more compounds which assist in the preparation and processing of the tablets.
  • Preferred lubricants are fatty acids or fatty acid derivatives, such as the alkali and alkaline earth salts of stearic, lauric and / or palmitic acid, and glyceryl mono- or glycerotristearate, glyceryl palmitostearate, sodium lauryl sulfate, sodium stearyl fumarate, zinc stearate, hydrogenated vegetable oils (lubritab), sodium benzoate, polyethylene glycol or talc, of which sodium stearyl fumarate and magnesium stearate are preferred.
  • compositions of this invention unlike the prior art irbesartan-containing drugs, need not necessarily contain a surfactant, such surfactant may, of course, be present in the pharmaceutical compositions of the present invention.
  • the surface active agent optionally contained in the irbesartan-containing pharmaceutical composition may be e.g. a poloxamer or polysorbate, preferably a polysorbate, in particular polysorbate 80 such as the commercial Tween 80.
  • the medicament according to the invention preferably contains no sodium lauryl sulfate as surface-active agent.
  • the pharmaceutical composition is preferably a tablet which can be prepared in the usual way by granulation or direct compression.
  • the tablet of the present invention preferably has such a release profile that 80% by weight or more of the irbesartan compound contained in the tablet is released within 30 minutes, more preferably within 15 minutes.
  • Another preferred release profile of the tablet according to the invention is such that 90% or more by weight of the irbesartan compound present in the tablet within 30 minutes and 80% or more (preferably 90% or more by weight) of the in The irbesartan compound present in the tablet is released within 15 minutes.
  • a tablet according to the invention has such a release profile even after 3 and more preferably after 6 months storage in a closed glass container under extreme conditions, ie at 4O 0 C and 75% relative humidity, as defined above.
  • the part of the irbesartan released within 30 minutes or within 15 minutes does not change by more than 30%, more preferably by not more than 20%, especially by storage for 3 months under the above extreme conditions not more than 10%, more preferably not more than 5%, most preferably not more than 2%.
  • the irbesartan-containing pharmaceutical composition of the present invention may be in the form of a tablet which may be film-coated with one or more coating agents.
  • the coating compositions are not particularly limited and known to those skilled in the art. Insofar as reference is made in the context of the present application to a release profile, it is the release profile of the uncoated tablet, or the tablet core, unless otherwise stated or apparent from the context.
  • the active ingredient of the pharmaceutical composition of the present invention is irbesartan which may be neutral or pharmaceutically acceptable salt, preferably irbesartan of polymorphic form A.
  • release profile is understood to mean the time course of the amount of irbesartan which is dissolved, based on the total amount of irbesartan. This release profile is obtained by dissolving a tablet in a USP apparatus II in 900 ml of 0.1 M hydrochloric acid at 37 ° C and a stirring speed of 50 rpm and the amount of irbesartan dissolved over a period of time, e.g. one hour, at different times, e.g. every five minutes, with the absorbance of 244 nm UV light as the reading.
  • the tablets are prepared from the irbesartan-containing pharmaceutical composition of the present invention by first mixing the low-substituted hydroxypropyl cellulose completely or partially with the irbesartan, then granulating this mixture with a binder, and the remainder of the disintegrating agents and the remaining excipients are then mixed with the granules and this mixture is compressed into tablets.
  • Particularly preferred is the following method:
  • the tablets according to the invention contain from 75 to 300 mg, e.g. 75, 150 or 300 mg irbesartan.
  • Figure 1 Release profile of a tablet of the invention according to Example 1 with
  • Figure 2 release profile of a tablet APROVEL ® (commercial product, as currently sold, for example, in Canada, irbesartan 300 mg), as new (X) and after 3 months storage at 40 0 C and 75% relative humidity (0) in one closed glass container (Comparative Example 1).
  • FIG. 3 Release profile of a tablet according to the invention according to Example 2 (300 mg Irbesartan).
  • FIG. 4 Release profile of a tablet according to the invention according to Example 3 (300 mg Irbesartan).
  • Percentages in the context of this application are by weight, unless otherwise stated or obvious to one skilled in the art. If the weight of a tablet is a reference, it is the weight of the uncoated tablet or the weight of the tablet, unless otherwise indicated or apparent to those skilled in the art.
  • An irbesartan-containing tablet according to the invention was prepared from the following constituents:
  • Example 1 The tablets obtained in Example 1 were subjected to a release test before the film coating, and the release profile was determined as indicated above. A sample of the uncoated tablets was stored for 3 months in a sealed glass container at 40 ° C. and 75% relative humidity, and then the release profile was determined. The result of the experiments is shown in FIG. The tablet releases irbesartan very rapidly and the release is practically unaffected by the storage of the drug.
  • Irbesartan-containing tablets according to the invention were prepared from the following constituents:
  • the 300 mg irbesartan tablet was subjected to a release test and the release profile was determined as indicated above. The result is shown in FIG.
  • the tablets may e.g. coated with a "Opadry Il white” coating system from Colorcon.
  • Irbesartan-containing tablets according to the invention were prepared from the following constituents
  • the 300 mg irbesartan tablet was subjected to a release test and the release profile was determined as indicated above. The result is shown in FIG.
  • the tablets may e.g. coated with a "Opadry Il white” coating system from Colorcon.

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  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Urology & Nephrology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Vascular Medicine (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne une composition pharmaceutique contenant de l'irbesartan, en particulier un comprimé fabriqué à partir de cette composition, contenant le principe actif, un délitant avec au moins une hydroxypropylcellulose faiblement substituée.
EP07711196A 2006-02-13 2007-02-13 Composition pharmaceutique contenant de l'irbesartan à libération rapide Withdrawn EP1983967A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102006006588A DE102006006588A1 (de) 2006-02-13 2006-02-13 Schnell freisetzende Irbesartan-haltige pharmazeutische Zusammensetzung
PCT/DE2007/000301 WO2007093168A2 (fr) 2006-02-13 2007-02-13 Composition pharmaceutique contenant de l'irbesartan à libération rapide

Publications (1)

Publication Number Publication Date
EP1983967A2 true EP1983967A2 (fr) 2008-10-29

Family

ID=38266017

Family Applications (1)

Application Number Title Priority Date Filing Date
EP07711196A Withdrawn EP1983967A2 (fr) 2006-02-13 2007-02-13 Composition pharmaceutique contenant de l'irbesartan à libération rapide

Country Status (5)

Country Link
US (2) US8309607B2 (fr)
EP (1) EP1983967A2 (fr)
CA (1) CA2642414C (fr)
DE (1) DE102006006588A1 (fr)
WO (1) WO2007093168A2 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2134326B1 (fr) * 2007-04-17 2011-11-16 Ratiopharm GmbH Compositions pharmaceutiques contenant de l'irbesartan
WO2011141783A2 (fr) 2010-04-13 2011-11-17 Micro Labs Limited Composition pharmaceutique comprenant de l'irbésartan

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5856362A (en) * 1994-09-02 1999-01-05 Glaxo Wellcome Inc. Medicaments for the treatment of toxoplasmosis
US5994348A (en) * 1995-06-07 1999-11-30 Sanofi Pharmaceutical compositions containing irbesartan
TW442301B (en) 1995-06-07 2001-06-23 Sanofi Synthelabo Pharmaceutical compositions containing irbesartan
CA2581111A1 (fr) * 1998-07-28 2000-02-10 Takeda Pharmaceutical Company Limited Preparation solide a desintegration rapide
EP1133984B1 (fr) * 2000-03-17 2005-05-11 Shin-Etsu Chemical Co., Ltd. Composition solide à base de hydroxypropylcellulose possédant un faible degré de substitution et procédé de préparation
US20020076437A1 (en) * 2000-04-12 2002-06-20 Sanjeev Kothari Flashmelt oral dosage formulation
JP2009513543A (ja) * 2003-07-16 2009-04-02 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング クロルタリドンの組み合わせ
PL1750862T3 (pl) * 2004-06-04 2011-06-30 Teva Pharma Kompozycja farmaceutyczna zawierająca irbesartan
WO2006013545A1 (fr) 2004-07-28 2006-02-09 Ranbaxy Laboratories Limited Compositions pharmaceutiques d'irbesartan
ATE462414T1 (de) 2006-01-09 2010-04-15 Krka D D Novo Mesto Irbesartan enthaltende feste zubereitung

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2007093168A2 *

Also Published As

Publication number Publication date
US20130059897A1 (en) 2013-03-07
CA2642414A1 (fr) 2007-08-23
WO2007093168A2 (fr) 2007-08-23
US20090220597A1 (en) 2009-09-03
CA2642414C (fr) 2014-08-26
WO2007093168A3 (fr) 2007-10-04
US8309607B2 (en) 2012-11-13
DE102006006588A1 (de) 2007-08-16

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