WO2011141783A2 - Pharmaceutical composition comprising irbesartan - Google Patents

Pharmaceutical composition comprising irbesartan Download PDF

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Publication number
WO2011141783A2
WO2011141783A2 PCT/IB2011/000729 IB2011000729W WO2011141783A2 WO 2011141783 A2 WO2011141783 A2 WO 2011141783A2 IB 2011000729 W IB2011000729 W IB 2011000729W WO 2011141783 A2 WO2011141783 A2 WO 2011141783A2
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WO
WIPO (PCT)
Prior art keywords
pharmaceutical composition
irbesartan
composition according
pharmaceutically acceptable
polysorbate
Prior art date
Application number
PCT/IB2011/000729
Other languages
French (fr)
Other versions
WO2011141783A3 (en
Inventor
Pradeep G. Surve
Pankaj S. Mandpe
Imran Y. Alana
Vijaykumar K. Shivpuje
Original Assignee
Micro Labs Limited
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 Micro Labs Limited filed Critical Micro Labs Limited
Publication of WO2011141783A2 publication Critical patent/WO2011141783A2/en
Publication of WO2011141783A3 publication Critical patent/WO2011141783A3/en

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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
    • A61K9/2013—Organic compounds, e.g. phospholipids, fats
    • A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • 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
    • 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
    • A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
    • A61K31/549—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame having two or more nitrogen atoms in the same ring, e.g. hydrochlorothiazide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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

Definitions

  • composition comprising Irbesartan.
  • Irbesartan is an angiotensin II receptor (AT1 subtype) antagonist.
  • Irbesartan is a non-peptide compound, chemically described as a 2-butyl-3-[p-(o-1 - -tetrazol-5-yl phenyl) benzyl]-1 , 3-diazaspiro [4.4] non-1 -en-4-one. It has the following structural formula.
  • Irbesartan is commercially available as a tablet dosage form. It is also available as a combination product with hydrochlorothiazide.
  • Irbesartan is practically insoluble in water. Further it has poor flow characteristics. These properties make it a difficult candidate to formulate.
  • US 6,342,247 discloses the difficulties involved in the formulation development of Irbesartan. Further, it discloses that the tablet should have a dissolution performance such that 80% or more of the irbesartan or a salt thereof contained in the tablet dissolves within 30 minutes. When combined with hydrochlorothiazide, the problems get complicated as hydrochlorothiazide is also a water insoluble drug.
  • US 5,994,348 discloses combination comprising Irbesartan and a diuretic
  • composition comprising at least 75% w/w irbesartan and at least one pharmaceutically-acceptable excipient.
  • US 2009/0030052 discloses pharmaceutical tablet composition comprising irbesartan and lactose said composition being essentially free of surfactant.
  • US 2009/0136571 discloses pharmaceutical composition comprising Irbesartan characterized in that it includes maltose.
  • US 2009/0220597 discloses pharmaceutical composition, comprising 20-90% by weight of irbesartan or a pharmaceutically acceptable salt thereof and at least 5% by weight of a disintegrant, at least 40% by weight of the disintegrant being low-substituted hydroxypropyl cellulose.
  • WO 05/025566 discloses oral pharmaceutical formulations of irbesartan that are prepared by the use of wet granulation method with alcohol as a wetting agent characterized in that, said formulations achieve improved dissolution profiles.
  • WO 06/013545 discloses pharmaceutical composition comprising more than about 70% by weight of irbesartan or salt thereof, alone or in combination with about 2% to about 20% by weight of hydrochlorothiazide, wherein the irbesartan and the hydrochlorothiazide comprise granules with a bulk density of between about 0.35 g/ml to about 0.65 g/ml.
  • WO 07/080074 discloses solid pharmaceutical formulation comprising, as an active ingredient, at least one of irbesartan and pharmaceutically acceptable salts thereof, and at least one disintegrant.
  • WO 08/125388 discloses pharmaceutical composition comprising irbesartan or a pharmaceutically acceptable salt thereof as active ingredient and more than 10 wt % of disintegrant, based on the total weight of the composition, characterized in that the composition does not comprise a silicon-containing antiadherent.
  • the inventors have developed a novel pharmaceutical composition comprising Irbesartan which is easy to formulate. It has been observed that when polysorbate in a particular concentration is used, the difficulties associated with the formulation development are eliminated. Specifically, stickiness causing problems in tabletting, especially in a high speed tablet press is avoided. Further, it enhances the dissolution of Irbesartan.
  • a pharmaceutical composition comprising Irbesartan and polysorbate.
  • the term 'Irbesartan' as used herein includes all the polymorphic forms and salts of Irbesartan.
  • the term 'Hydrochlorothiazide' includes all the polymorphic forms and salts of Hydrochlorothiazide.
  • the essential feature of invention is the presence of polysorbate.
  • the polysorbates are a class of solubilizers used for the solubilization of the drugs.
  • the polysorbate may be present in the concentration ranging from 1 to 5 % by weight of the composition.
  • the commercially available polysorbates like Tween 20, Tween 40, Tween 60 and Tween 80 may also be used.
  • the pharmaceutical composition may be a solid dosage form.
  • the solid dosage form may be one or more of tablet, capsule, powder, disc, caplet, granules, pellets, granules in capsule, minitablets, minitablets in capsule, pellets in capsule, sachet and the like.
  • the solid dosage form also includes multilayer tablets.
  • the core as disclosed herein includes uncoated solid dosage form.
  • the pharmaceutical composition contains Irbesartan as active ingredient.
  • the active ingredient may be present in the form of powder, granules, pellets, beads, microtablets, minitablets and crystals.
  • the pharmaceutical composition comprises one or more pharmaceutically acceptable inert excipients.
  • the pharmaceutically acceptable inert excipients may be one or more of diluents, binders, disintegrants, lubricants, glidants, solvents and the like.
  • Suitable diluents may include one or more of microcrystalline cellulose, lactose, mannitol, calcium phosphate, calcium sulfate, kaolin, dry starch, powdered sugar, and the like.
  • Suitable binder may be one or more of, povidone, starch, stearic acid, gums, hydroxypropylmethyl cellulose and the like.
  • Suitable disintegrant may be one or more of starch, croscarmellose sodium, crospovidone, sodium starch glycolate and the like.
  • Suitable solvents may be one or more of isopropyl alcohol, methylene chloride, purified water and the like.
  • Suitable lubricant may be one or more of magnesium stearate, zinc stearate, calcium stearate, stearic acid, sodium stearyl fumarate, hydrogenated vegetable oil, glyceryl behenate and the like.
  • Suitable glidant may be one or more of colloidal silicon dioxide, talc or cornstarch and the like.
  • the pharmaceutical composition may further contain hydrochlorothiazide.
  • the pharmaceutical composition may optionally be film coated.
  • the film coating may comprise one or more of film formers, solvents, plasticizers and the like.
  • Suitable film formers may be one or more of hydroxypropyl methyl cellulose, methyl hydroxyethyl cellulose, ethyl cellulose, hydroxypropyl cellulose, povidone, sodium carboxymethyl cellulose, polyethylene glycol, acrylates and the like.
  • Suitable solvents may be one or more of water, ethanol, methanol, isopropanol, chloroform, acetone, methylethyl ketone, methylene chloride and the like.
  • Suitable plasttcizers may be one or more of propylene glycol, castor oil, glycerin, polyethylene glycol, polysorbates, and the like.
  • step (c) Granulating the mixture in step (a) with solution formed in step (b) to form granules
  • step (d) Optionally compressing the granules formed in step (c) using suitable toolings.
  • the pharmaceutical composition may be prepared by processes those known to ordinary skill in the art. While the invention has been described in terms of its specific embodiments, certain modifications and equivalents will be apparent to those skilled in the art and are intended to be included within the scope of the invention.
  • step 3 The mixture of step 1 was granulated with solution of step 2 to form granules.
  • step 3 The granules formed in step 3 were milled and dried.
  • Sodium starch glycolate, microcrystalline cellulose and colloidal silicon dioxide were blended with the dried granules to form a blend.
  • step 5 The blend formed in step 5 was mixed with magnesium stearate to form a mixture.
  • step 6 The mixture formed in step 6 was compressed using suitable toolings.

Landscapes

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

Abstract

There is provided a pharmaceutical composition comprising Irbesartan.

Description

PHARMACEUTICAL COMPOSITION COMPRISING IRBESARTAN
Description
There is provided a pharmaceutical composition comprising Irbesartan.
Irbesartan is an angiotensin II receptor (AT1 subtype) antagonist. Irbesartan is a non-peptide compound, chemically described as a 2-butyl-3-[p-(o-1 - -tetrazol-5-yl phenyl) benzyl]-1 , 3-diazaspiro [4.4] non-1 -en-4-one. It has the following structural formula.
Figure imgf000002_0001
Irbesartan is commercially available as a tablet dosage form. It is also available as a combination product with hydrochlorothiazide.
Irbesartan is practically insoluble in water. Further it has poor flow characteristics. These properties make it a difficult candidate to formulate. US 6,342,247 discloses the difficulties involved in the formulation development of Irbesartan. Further, it discloses that the tablet should have a dissolution performance such that 80% or more of the irbesartan or a salt thereof contained in the tablet dissolves within 30 minutes. When combined with hydrochlorothiazide, the problems get complicated as hydrochlorothiazide is also a water insoluble drug.
US 5,994,348 discloses combination comprising Irbesartan and a diuretic;
US 2005/0271720 discloses composition comprising at least 75% w/w irbesartan and at least one pharmaceutically-acceptable excipient. US 2009/0030052 discloses pharmaceutical tablet composition comprising irbesartan and lactose said composition being essentially free of surfactant.
US 2009/0136571 discloses pharmaceutical composition comprising Irbesartan characterized in that it includes maltose.
US 2009/0220597 discloses pharmaceutical composition, comprising 20-90% by weight of irbesartan or a pharmaceutically acceptable salt thereof and at least 5% by weight of a disintegrant, at least 40% by weight of the disintegrant being low-substituted hydroxypropyl cellulose.
WO 05/025566 discloses oral pharmaceutical formulations of irbesartan that are prepared by the use of wet granulation method with alcohol as a wetting agent characterized in that, said formulations achieve improved dissolution profiles.
WO 06/013545 discloses pharmaceutical composition comprising more than about 70% by weight of irbesartan or salt thereof, alone or in combination with about 2% to about 20% by weight of hydrochlorothiazide, wherein the irbesartan and the hydrochlorothiazide comprise granules with a bulk density of between about 0.35 g/ml to about 0.65 g/ml.
WO 07/080074 discloses solid pharmaceutical formulation comprising, as an active ingredient, at least one of irbesartan and pharmaceutically acceptable salts thereof, and at least one disintegrant.
WO 08/125388 discloses pharmaceutical composition comprising irbesartan or a pharmaceutically acceptable salt thereof as active ingredient and more than 10 wt % of disintegrant, based on the total weight of the composition, characterized in that the composition does not comprise a silicon-containing antiadherent. The inventors have developed a novel pharmaceutical composition comprising Irbesartan which is easy to formulate. It has been observed that when polysorbate in a particular concentration is used, the difficulties associated with the formulation development are eliminated. Specifically, stickiness causing problems in tabletting, especially in a high speed tablet press is avoided. Further, it enhances the dissolution of Irbesartan.
In one aspect of the invention, there is provided a pharmaceutical composition comprising Irbesartan and polysorbate.
The term 'Irbesartan' as used herein includes all the polymorphic forms and salts of Irbesartan. The term 'Hydrochlorothiazide' includes all the polymorphic forms and salts of Hydrochlorothiazide. The essential feature of invention is the presence of polysorbate. The polysorbates are a class of solubilizers used for the solubilization of the drugs. The polysorbate may be present in the concentration ranging from 1 to 5 % by weight of the composition. The commercially available polysorbates like Tween 20, Tween 40, Tween 60 and Tween 80 may also be used.
The pharmaceutical composition may be a solid dosage form. The solid dosage form may be one or more of tablet, capsule, powder, disc, caplet, granules, pellets, granules in capsule, minitablets, minitablets in capsule, pellets in capsule, sachet and the like. The solid dosage form also includes multilayer tablets. The core as disclosed herein includes uncoated solid dosage form.
The pharmaceutical composition contains Irbesartan as active ingredient. The active ingredient may be present in the form of powder, granules, pellets, beads, microtablets, minitablets and crystals. The pharmaceutical composition comprises one or more pharmaceutically acceptable inert excipients. The pharmaceutically acceptable inert excipients may be one or more of diluents, binders, disintegrants, lubricants, glidants, solvents and the like.
Suitable diluents may include one or more of microcrystalline cellulose, lactose, mannitol, calcium phosphate, calcium sulfate, kaolin, dry starch, powdered sugar, and the like. Suitable binder may be one or more of, povidone, starch, stearic acid, gums, hydroxypropylmethyl cellulose and the like.
Suitable disintegrant may be one or more of starch, croscarmellose sodium, crospovidone, sodium starch glycolate and the like.
Suitable solvents may be one or more of isopropyl alcohol, methylene chloride, purified water and the like.
Suitable lubricant may be one or more of magnesium stearate, zinc stearate, calcium stearate, stearic acid, sodium stearyl fumarate, hydrogenated vegetable oil, glyceryl behenate and the like.
Suitable glidant may be one or more of colloidal silicon dioxide, talc or cornstarch and the like.
The pharmaceutical composition may further contain hydrochlorothiazide.
The pharmaceutical composition may optionally be film coated. The film coating may comprise one or more of film formers, solvents, plasticizers and the like. Suitable film formers may be one or more of hydroxypropyl methyl cellulose, methyl hydroxyethyl cellulose, ethyl cellulose, hydroxypropyl cellulose, povidone, sodium carboxymethyl cellulose, polyethylene glycol, acrylates and the like. Suitable solvents may be one or more of water, ethanol, methanol, isopropanol, chloroform, acetone, methylethyl ketone, methylene chloride and the like.
Suitable plasttcizers may be one or more of propylene glycol, castor oil, glycerin, polyethylene glycol, polysorbates, and the like.
In another aspect, there is provided a process for preparing a pharmaceutical composition comprising Irbesartan, the process comprising
(a) Mixing Irbesartan with pharmaceutically acceptable inert excipients to form a mixture,
(b) Adding polysorbate in water optionally with pharmaceutically acceptable inert excipients to form a solution,
(c) Granulating the mixture in step (a) with solution formed in step (b) to form granules,
(d) Optionally compressing the granules formed in step (c) using suitable toolings.
The pharmaceutical composition may be prepared by processes those known to ordinary skill in the art. While the invention has been described in terms of its specific embodiments, certain modifications and equivalents will be apparent to those skilled in the art and are intended to be included within the scope of the invention.
S SN Ingredients Mg/Tab
1. Irbesartan (JSP 75.00 150.00 300.00
2. Lactose 22.50 45.00 90.00
3. Sodium starch glycolate 1.50 3.00 6.00
4. Hydroxypropyl methyl cellulose 3.75 7.50 15.00
5. Polysorbate 2.25 4.50 9.00
6. Purified Water Q.S. Q.S. Q.S.
7. Microcrystalline Cellulose 31.50 63.00 126.00
8. Sodium starch glycolate 10.5 21.00 42.00
9. Colloidal silicon dioxide 1.50 3.00 6.00
10. Magnesium Stearate USNF 1.50 3.00 6.00
Tablet weight 150.00 300.00 600.00
Table-1 : Pharmaceutical composition of the invention
Procedure:
1. Irbesartan, Lactose and Sodium starch were mixed to form a mixture.
2. A solution of Hydroxypropyl methyl cellulose & Polysorbate 80 was prepared in purified water.
3. The mixture of step 1 was granulated with solution of step 2 to form granules.
4. The granules formed in step 3 were milled and dried.
5. Sodium starch glycolate, microcrystalline cellulose and colloidal silicon dioxide were blended with the dried granules to form a blend.
6. The blend formed in step 5 was mixed with magnesium stearate to form a mixture.
7. The mixture formed in step 6 was compressed using suitable toolings.

Claims

1. A pharmaceutical composition comprising Irbesartan and polysorbate.
2. The pharmaceutical composition according to claim 1 , wherein the composition is in the form of solid dosage form.
3. The pharmaceutical composition according to claim 2, wherein composition is in the form of tablet.
4. The pharmaceutical composition according to claim 1 , wherein the polysorbate is present in the concentration ranging from 1 to 5 % by weight of composition.
5. The pharmaceutical composition according to claim 1 , wherein the composition further comprises pharmaceutically acceptable inert excipients.
6. The pharmaceutical composition according to claim 1 , wherein the composition is film coated.
7. The pharmaceutical composition according to claim 6, wherein the film coating comprises one or more of film formers, solvents, plasticizers.
8. The pharmaceutical composition according to claim 1 , further comprising hydrochlorothiazide.
9. A process for preparing a pharmaceutical composition comprising Irbesartan, the process comprising
(a) Mixing Irbesartan with pharmaceutically acceptable inert excipients to form a mixture, (b) Adding polysorbate in water optionally with pharmaceutically acceptable inert excipients to form a solution,
(c) Granulating the mixture in step (a) with solution formed in step (b) to form granules,
(d) Optionally compressing the granules formed in step (c) using suitable toolings.
10. A pharmaceutical composition as herein above described in the specification.
PCT/IB2011/000729 2010-04-13 2011-04-05 Pharmaceutical composition comprising irbesartan WO2011141783A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1210/MUM/2010 2010-04-13
IN1210MU2010 2010-04-13

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WO2011141783A2 true WO2011141783A2 (en) 2011-11-17
WO2011141783A3 WO2011141783A3 (en) 2012-04-26

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Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5994348A (en) 1995-06-07 1999-11-30 Sanofi Pharmaceutical compositions containing irbesartan
WO2005025566A1 (en) 2003-09-18 2005-03-24 Nobel Ilac Sanayi Ve Ticaret As Oral pharmaceutical formulations containing the active ingredient irbesartan
US20050271720A1 (en) 2004-06-04 2005-12-08 Teva Pharmaceutical Industries, Ltd. Pharmaceutical composition containing irbesartan
WO2006013545A1 (en) 2004-07-28 2006-02-09 Ranbaxy Laboratories Limited Pharmaceutical compositions of irbesartan
WO2007080074A1 (en) 2006-01-09 2007-07-19 Krka, D.D. Novo Mesto Solid pharmaceutical composition comprising irbesartan
WO2008125388A1 (en) 2007-04-17 2008-10-23 Ratiopharm Gmbh Pharmaceutical compositions comprising irbesartan
US20090030052A1 (en) 2006-02-17 2009-01-29 Alembic Limited Pharmaceutical tablet compositions containing irbesartan
US20090138571A1 (en) 2005-12-12 2009-05-28 Industrial Technology Research Institute Control method for modifying engineering information from a remote work site and a system of the same
US20090220597A1 (en) 2006-02-13 2009-09-03 Ratiopharm Gmbh Rapid release irbesartan-containing pharmaceutical composition

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2735365B1 (en) * 1995-06-14 1997-09-05 Sanofi Sa USE OF AN ANGIOTENSIN II ANTAGONIST AND A BENZOFURANE DERIVATIVE FOR THE PREPARATION OF A MEDICAMENT USEFUL IN THE TREATMENT OF CARDIOVASCULAR CONDITIONS
CN1732953B (en) * 2005-09-02 2010-05-05 姚俊华 Dispersible tablet for treating hypertension
EP2153822A1 (en) * 2008-08-13 2010-02-17 Lek Pharmaceuticals D.D. Granulation of active pharmaceutical ingredients
JP5296456B2 (en) * 2008-08-26 2013-09-25 大日本住友製薬株式会社 Irbesartan-containing pharmaceutical composition with good dissolution and orally disintegrating tablet

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5994348A (en) 1995-06-07 1999-11-30 Sanofi Pharmaceutical compositions containing irbesartan
US6342247B1 (en) 1995-06-07 2002-01-29 Sanofi-Synthelabo Pharmaceutical compositions containing irbesartan
WO2005025566A1 (en) 2003-09-18 2005-03-24 Nobel Ilac Sanayi Ve Ticaret As Oral pharmaceutical formulations containing the active ingredient irbesartan
US20050271720A1 (en) 2004-06-04 2005-12-08 Teva Pharmaceutical Industries, Ltd. Pharmaceutical composition containing irbesartan
WO2006013545A1 (en) 2004-07-28 2006-02-09 Ranbaxy Laboratories Limited Pharmaceutical compositions of irbesartan
US20090138571A1 (en) 2005-12-12 2009-05-28 Industrial Technology Research Institute Control method for modifying engineering information from a remote work site and a system of the same
WO2007080074A1 (en) 2006-01-09 2007-07-19 Krka, D.D. Novo Mesto Solid pharmaceutical composition comprising irbesartan
US20090220597A1 (en) 2006-02-13 2009-09-03 Ratiopharm Gmbh Rapid release irbesartan-containing pharmaceutical composition
US20090030052A1 (en) 2006-02-17 2009-01-29 Alembic Limited Pharmaceutical tablet compositions containing irbesartan
WO2008125388A1 (en) 2007-04-17 2008-10-23 Ratiopharm Gmbh Pharmaceutical compositions comprising irbesartan

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