WO2006087028A1 - Composition containing chitosan for sustained drug release - Google Patents
Composition containing chitosan for sustained drug release Download PDFInfo
- Publication number
- WO2006087028A1 WO2006087028A1 PCT/EP2005/013663 EP2005013663W WO2006087028A1 WO 2006087028 A1 WO2006087028 A1 WO 2006087028A1 EP 2005013663 W EP2005013663 W EP 2005013663W WO 2006087028 A1 WO2006087028 A1 WO 2006087028A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- chitosan
- solution
- drug
- release
- sodium
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/61—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule the organic macromolecular compound being a polysaccharide or a derivative thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
Definitions
- the present invention relates to a composition for sustained drug release and the use thereof.
- Chitosan is a natural substance that is highly available in nature. It is inexpensive, non-toxic, biodegradable, and biocompatible when compared with other polymers. Pharmaceutical uses of chitosan are very numerous. The scientific and medical literature lists hundreds of industrial, medical and dietary applications for chitosan, see J. Karlsen and O. Skaugrud, Exicipient Properties of Chitosan, Manufacturing Chemist, 62, p. 18, 1991, and I. Orienti, K. Aieda, C. Ponti, E. Gianasi, V. Zecchi, Progesterone Loaded Chitosan Microspheres, Effect of triethylene glycol glutarate linked to the chitosan molecule on drug release, S.T.P. Pharm. Sci., 6, p. 424-429, 1996. Chitosan is considered to be non-digestible by humans when taken by oral route due to lack of chitosanases, which are present, however, in some bacteria.
- chitosan As a drug delivery vehicle, chitosan is considered as the drug carrier for the 21 st century. It has been examined extensively by the pharmaceutical industry for its potential in controlled drug delivery systems. The use of chitosan in controlled drug delivery systems aims to prepare solid dosage forms including microparticles or macromolecular systems kinetically controlling drug release in order to make the release more dependent on the pharmaceutical formulation than the physicochemical characteristics of the drug. Examples are as follows: chitosan direct compression tablets, chitosan microspheres that adhere to stomach wall, chitosan cross-linked with acetic anhydride and glutaraldehyde forms a spongy structure upon exposure to dissolution medium, and chitosan beads prepared as controlled release drug carrier.
- Solid dosage forms can not be given to children, babies and newborns, there is a difficulty in swallowing solid dosage forms compared to liquid forms. Further, there are certain adults that can not swallow tablets and, additionally drug dose can be given in larger amount in liquid dosage forms compared to solid dosage forms, especially for drugs of high strength. It is therefore the object of the present invention to overcome the disadvantages of the prior art and to provide a composition for sustained drug release, which may be easily and reliable administered to a patient.
- composition for sustained drug release comprising: a) chitosan dissolved in a solvent having a pH of below about 4.0, wherein the chitosan is selected from the group of chitosans precipitating in a pH range of between about 3.0 and about 7.5 and b) at least one drug compound soluble in the chitosan solution.
- the chitosan is selected from the group of chitosans precipitating in a pH range of between 5.0 and 7.5, preferably 6.0 to 7.5, more preferably 6.5 to 7.5, and most preferably 7.0 and 7.5.
- the solvent is 0.1 M HCl and/or water.
- the drug is diclofenac, ibuprofen sodium, valproate sodium and/or the like.
- a composition may be provided, wherein the chitosan has a molecular weight of about 500 to about 400,000, preferably of about 500 to about 100,000.
- the drug is present in the liquid composition in an amount of about 0.1 - 10 % w/v, more preferably 0.1 - 2 % w/v.
- chitosan is present in the liquid composition in an amount of about 1 - 15 % w/v, more preferably 1 - 10 % w/v, most preferably 1 - 5 % w/v.
- the inventive composition may be used for sustained drug release.
- the liquid composition is administered orally.
- the stomach may be protected from the harsh side effect of acidic drugs, such as diclofenac sodium or ibuprofen sodium, since the release of the drug is mainly sustained to the intestinal tract, wherein the pH is somewhat higher.
- acidic drugs such as diclofenac sodium or ibuprofen sodium
- diclofenac sodium or ibuprofen sodium seemed to be insoluble in acidic media.
- the pH of the human digestive tract varies between 1.0-7.8, wherein the stomach being acidic (pH around 1.0-3.0) and the small intestine having a pH of about 5.50-7.8.
- the release of a drug may be targeted to the specific regions in the gastrointestinal tract, for example duodenum and colon. It is assumed that the sustained release depends, amongst others, on the molecular weight of chitosan used with the drug.
- Fig. 1 illustrates the percentage of diclofenac sodium being free in chitosan diclofenac sodium solution using chitosan of a fraction at pH 5.00; -A-
- Fig. 2 illustrates the percentage of diclofenac sodium being free in chitosan diclofenac sodium solution using chitosan of a fraction at pH 6.00;
- Fig. 3 illustrates the percentage of diclofenac sodium being free in chitosan diclofenac sodium solution using chitosan of a fraction at pH 7.00;
- Fig. 4 illustrates the percentage of diclofenac sodium, being free in chitosan diclofenac sodium solution using chitosan of a fraction at pH 7.50;
- Fig. 5 illustrates ibuprofen sodium plasma concentration time profiles of sustained release solution (molecular weight of chitosan ⁇ 3000) compared to an immediate release solution;
- Fig. 6 illustrates ibuprofen sodium plasma concentration time profiles of sustained release solution (with chitosan having a molecular weight ⁇ 5000) compared to immediate release solution;
- Fig. 7 illustrates ibuprofen sodium plasma concentration time profiles of sustained release solution (chitosan having a molecular weight of ⁇ 10000) compared to immediate release solution.
- a chitosan fraction (or several fractions) have to be prepared from commercially available chitosan mixture.
- the chitosan oligosaccharide mixture may be a mixture comprising chitosan with a molecular weight of not more than 2,000, not more than 3,000, not more than 5,000, not more than 10,000, not more than 50,000, between 10,000 and 100,000, not more than 100,000 or 250,000-400,000, for example.
- Each chitosan solution was then filtered using a 0.45 ⁇ m cellulose acetate filter.
- step 7 adjust pH of the filtered solution obtained in step 6 to pH 7.0 using 1.0 M NaOH, filtrate and collect the precipitate, and
- chitosan precipitates obtained above in a pH range of 5.0 to 8.0 with chitosans having different molecular weights were used for further evaluation, and solutions for sustained drug release were prepared using that chitosan fractions and different drugs.
- Solution (2) 1.667 ml of 15 mg/ml of diclofenac sodium in propylene glycol solution was added to 20 ml of distilled water.
- Solution (4) 0.1 M HCl solution was used and its pH was changed similar to the other solution [used as blank for solution 2].
- the percentage of drug release from the chitosan fraction prepared according to step B3 (molecular weight not more than 100,000) is summarized as below.
- the drug release is measured by standard dissolution method, which is known to someone skilled in the art, see e.g., M. Sheu, H. Chou, C. Kao, C. Liu, T. Sokotoski, Dissolution of Diclofenac Sodium from Matrix Tablets, Int. J. Pharm., 85, pp. 57 - 63, 1992.
- Fig. 1 illustrates the results given in table 1.
- a chitosan solution was prepared as in example 1 above, and additionally four solutions as in example 1 were prepared. Further, the pH was increased by adding tri-sodium phosphate according to the following scheme:
- a chitosan solution as well as solutions for evaluating the dissolution behavior were prepared according to example 1 and the pH of these solutions was amended using tri-sodium phosphate according to the following scheme.
- step B7 The percentage of drug release from the chitosan fraction obtained in step B7 (molecular weight not more than 10,000) is summarized as below.
- a chitosan solution as well as solutions for evaluating the dissolution behavior have been prepared according to example 1. The pH of these solutions was increased using tri-sodium phosphate according to the following scheme.
- step B8 The percentage of drug release from the chitosan fraction obtained in step B8 (molecular weight not more than 5,000) is summarized as below.
- diclofenac sodium shows sustained release as pH is changing using different fractions of chitosan solutions. These situations resemble the gastrointestinal tract conditions when human being takes a solution orally.
- the amount of the drug loaded in chitosan solution was 25 mg diclofenac sodium/22 ml. This dose seems realistic since the commercial diclofenac sodium doses start from 12.5 mg to 150 mg.
- Ibuprofen sodium is another model drug that is used to prove the sustained release idea in-vivo.
- Chitosan of different molecular weights (Mw ⁇ 3000, ⁇ 5000 and ⁇ 10000) were evaluated for controlling the release of ibuprofen.
- Each sustained release chitosan conjugate solution contained a complex of ibuprofen sodium with chitosan.
- the final pH of the solutions were 6.60.
- the dose of the conjugate oral solutions was 30 mg of ibuprofen/kg rabbit.
- a reference immediate release oral solution was given with a dose of 10 mg of ibuprofen/kg rabbit.
- Sample Preparation Transfer 100 ⁇ L of plasma sample to test tube, add 10 ⁇ L of Internal STD Stock solution, add 0.25 ml of 1 M HCl 5 shake for 30 seconds, add 5 niL of (85:15)(Hexane: Isopropanol), shake with vortex for 1 min., centrifuge at 3000 rpm for 10 min., transfer 4 ml of organic layer to new test tube, evaporate the organic solvent using an air shower, and reconstitute with 1 ml mobile phase. The method was evaluated for specificity showing that there is no interference with the ibuprofen peak. Recovery was 85-90% for ibuprofen. The calibration curve was linear over the concentration 0.5-10 ⁇ g/ml.
- the chitosan conjugate solution contained 12 mg ibupro fen/ml.
- the dose of the drug given to each rabbit was 30 mg/kg.
- the immediate release aqueous solution contained ibuprofen sodium with a concentration of 4 mg ibuprofen/ml.
- the dose of the drug given as a reference was 10 mg/kg. This dose (10 mg/kg rabbit) is equivalent to 600 mg ibuprofen given to human subject weighted 60 kg (The usual human immediate release dose for adults is 200-600mg given 3 times per day).
- the formula should contain total daily dose and to be given once i.e. 30 mg/kg. This justifies the dose of the sustained release solution being three times more than the immediate release one.
- One of the advantages of sustained release is to decrease the frequency of drug dosing by giving the dose once per day.
- Figures 5-7 show that the release profiles of ibuprofen from the conjugate samples were pH dependent. As drug passes through a certain portion of different pH some of the drug is released. In the first portion, drug being released is somewhat equivalent or less than that released by an immediate release solution of ibuprofen.
- ibuprofen shows sustained release as it passes the gastrointestinal tract when given as a chitosan conjugate solution.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Inorganic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP05822507A EP1848397A1 (en) | 2005-02-17 | 2005-12-19 | Composition containing chitosan for sustained drug release |
CA002598364A CA2598364A1 (en) | 2005-02-17 | 2005-12-19 | Composition containing chitosan for sustained drug release |
JP2007555462A JP2008530148A (en) | 2005-02-17 | 2005-12-19 | Chitosan-containing composition for sustained release medicine |
US11/816,308 US20100130612A1 (en) | 2005-02-17 | 2005-12-19 | Composition containing chitosan for sustained drug release |
AU2005327852A AU2005327852A1 (en) | 2005-02-17 | 2005-12-19 | Composition containing chitosan for sustained drug release |
BRPI0520078-4A BRPI0520078A2 (en) | 2005-02-17 | 2005-12-19 | chitosan-containing composition for sustained drug release |
EA200701735A EA200701735A1 (en) | 2005-02-17 | 2005-12-19 | COMPOSITION, CONTAINING CHITOSAN, FOR PROLONGED RELEASE OF MEDICINE |
AP2007004156A AP2007004156A0 (en) | 2005-02-17 | 2005-12-19 | Composition containing chitosan for sustained drugrelease |
TNP2007000288A TNSN07288A1 (en) | 2005-02-17 | 2007-07-24 | Composition containing chitosan for sustained drug release |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP05003405.7 | 2005-02-17 | ||
EP05003405A EP1693051B1 (en) | 2005-02-17 | 2005-02-17 | Composition containing chitosan for sustained drug release |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2006087028A1 true WO2006087028A1 (en) | 2006-08-24 |
Family
ID=34933799
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2005/013663 WO2006087028A1 (en) | 2005-02-17 | 2005-12-19 | Composition containing chitosan for sustained drug release |
Country Status (16)
Country | Link |
---|---|
US (1) | US20100130612A1 (en) |
EP (2) | EP1693051B1 (en) |
JP (1) | JP2008530148A (en) |
KR (1) | KR20070104643A (en) |
CN (1) | CN101128183A (en) |
AP (1) | AP2007004156A0 (en) |
AT (1) | ATE397439T1 (en) |
AU (1) | AU2005327852A1 (en) |
BR (1) | BRPI0520078A2 (en) |
CA (1) | CA2598364A1 (en) |
DE (1) | DE602005007319D1 (en) |
EA (1) | EA200701735A1 (en) |
MA (1) | MA29317B1 (en) |
TN (1) | TNSN07288A1 (en) |
WO (1) | WO2006087028A1 (en) |
ZA (1) | ZA200706807B (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102009024542A1 (en) * | 2009-06-10 | 2010-12-16 | Arivine Pharma Ag | Compositions based on chitosan oligosaccharides |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1955711A1 (en) * | 2007-02-09 | 2008-08-13 | The Jordanian Pharmaceutical Manufacturing Co. | Composition comprising covalent conjugates of chitosan and an acidic drug for parenteral administration |
EP1955693A1 (en) * | 2007-02-09 | 2008-08-13 | The Jordanian Pharmaceutical Manufacturing Co. | Composition comprising chitosan and an acidic drug for oral controlled release |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0343306A1 (en) * | 1985-09-16 | 1989-11-29 | Carulla Vekar, S.A. | Liquid pharmaceutical preparation based on theophylline with a retarding effect, and process for producing it |
JPH05339149A (en) * | 1992-02-27 | 1993-12-21 | Taisho Pharmaceut Co Ltd | Sustained release suspension preparation |
WO1995022315A1 (en) * | 1994-02-18 | 1995-08-24 | Ciba-Geigy Ag | Liquid ophthalmic sustained release delivery system |
WO2004069230A1 (en) * | 2003-02-06 | 2004-08-19 | Advanced Biopolymers As | Pharmaceutical compositions comprising an active agent and chitosan for sustained drug release or mucoadhesion |
JP3605613B2 (en) * | 2001-10-01 | 2004-12-22 | 有限会社関西キトサン | Liquid for plant cultivation |
-
2005
- 2005-02-17 EP EP05003405A patent/EP1693051B1/en not_active Not-in-force
- 2005-02-17 DE DE602005007319T patent/DE602005007319D1/en not_active Expired - Fee Related
- 2005-02-17 AT AT05003405T patent/ATE397439T1/en not_active IP Right Cessation
- 2005-12-19 CA CA002598364A patent/CA2598364A1/en not_active Abandoned
- 2005-12-19 AP AP2007004156A patent/AP2007004156A0/en unknown
- 2005-12-19 AU AU2005327852A patent/AU2005327852A1/en not_active Abandoned
- 2005-12-19 EP EP05822507A patent/EP1848397A1/en not_active Withdrawn
- 2005-12-19 ZA ZA200706807A patent/ZA200706807B/en unknown
- 2005-12-19 WO PCT/EP2005/013663 patent/WO2006087028A1/en not_active Application Discontinuation
- 2005-12-19 CN CNA2005800481867A patent/CN101128183A/en active Pending
- 2005-12-19 KR KR1020077020070A patent/KR20070104643A/en not_active Application Discontinuation
- 2005-12-19 JP JP2007555462A patent/JP2008530148A/en not_active Withdrawn
- 2005-12-19 BR BRPI0520078-4A patent/BRPI0520078A2/en not_active IP Right Cessation
- 2005-12-19 EA EA200701735A patent/EA200701735A1/en unknown
- 2005-12-19 US US11/816,308 patent/US20100130612A1/en not_active Abandoned
-
2007
- 2007-07-24 TN TNP2007000288A patent/TNSN07288A1/en unknown
- 2007-09-06 MA MA30195A patent/MA29317B1/en unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0343306A1 (en) * | 1985-09-16 | 1989-11-29 | Carulla Vekar, S.A. | Liquid pharmaceutical preparation based on theophylline with a retarding effect, and process for producing it |
JPH05339149A (en) * | 1992-02-27 | 1993-12-21 | Taisho Pharmaceut Co Ltd | Sustained release suspension preparation |
WO1995022315A1 (en) * | 1994-02-18 | 1995-08-24 | Ciba-Geigy Ag | Liquid ophthalmic sustained release delivery system |
JP3605613B2 (en) * | 2001-10-01 | 2004-12-22 | 有限会社関西キトサン | Liquid for plant cultivation |
WO2004069230A1 (en) * | 2003-02-06 | 2004-08-19 | Advanced Biopolymers As | Pharmaceutical compositions comprising an active agent and chitosan for sustained drug release or mucoadhesion |
Non-Patent Citations (3)
Title |
---|
ACIKGOZ M ET AL: "CHITOSAN MICROSPHERES OF DICLOFENAC SODIUM, II: IN VITRO AND IN VIVO EVALUATION", PHARMAZIE, DIE, PHARMAZEUTISCHER VERL., ESCHBORN, DE, vol. 50, no. 4, 1 April 1995 (1995-04-01), pages 275 - 277, XP000494763, ISSN: 0031-7144 * |
DATABASE WPI Section Ch Week 199404, Derwent World Patents Index; Class B07, AN 1994-031721, XP002336182 * |
DATABASE WPI Section Ch Week 200501, Derwent World Patents Index; Class C03, AN 2003-817546, XP002336212 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102009024542A1 (en) * | 2009-06-10 | 2010-12-16 | Arivine Pharma Ag | Compositions based on chitosan oligosaccharides |
WO2010142400A2 (en) | 2009-06-10 | 2010-12-16 | Arivine Pharma Ag | Chitosan oligosaccharide-based compositions |
Also Published As
Publication number | Publication date |
---|---|
CA2598364A1 (en) | 2006-08-24 |
KR20070104643A (en) | 2007-10-26 |
EP1848397A1 (en) | 2007-10-31 |
EP1693051B1 (en) | 2008-06-04 |
CN101128183A (en) | 2008-02-20 |
JP2008530148A (en) | 2008-08-07 |
EP1693051A1 (en) | 2006-08-23 |
BRPI0520078A2 (en) | 2009-04-14 |
DE602005007319D1 (en) | 2008-07-17 |
ZA200706807B (en) | 2008-10-29 |
ATE397439T1 (en) | 2008-06-15 |
US20100130612A1 (en) | 2010-05-27 |
AU2005327852A1 (en) | 2006-08-24 |
TNSN07288A1 (en) | 2008-12-31 |
AP2007004156A0 (en) | 2007-10-31 |
EA200701735A1 (en) | 2008-02-28 |
MA29317B1 (en) | 2008-03-03 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
FI85216B (en) | FOERFARANDE FOER FARMSTAELLNING AV ETT ORALT ADMINISTRERBART PHARMACEUTICAL PREPARATION AV 5-AMINO-SALICYLSYRA. | |
CN107375945B (en) | Donepezil cyclodextrin inclusion compound and oral instant film agent containing same | |
Riekes et al. | Evaluation of oral carvedilol microparticles prepared by simple emulsion technique using poly (3-hydroxybutyrate-co-3-hydroxyvalerate) and polycaprolactone as polymers | |
US20230255980A1 (en) | Taste-masking oral formulations of fasudil | |
MX2008015015A (en) | Oral composition comprising 3-[5-[4-(cyclopentyloxy) -2-hydroxybenzoyl]-2-[(3-hydroxy-1,2-benzisoxazol-6- yl)methoxy]phenyl]propionic acid or salt thereof. | |
US20100130612A1 (en) | Composition containing chitosan for sustained drug release | |
JP7503632B2 (en) | Liquid tasimelteon formulations and methods of using same | |
EP1955710A1 (en) | Aqueous composition comprising chitosan and an acidic drug | |
EP1955693A1 (en) | Composition comprising chitosan and an acidic drug for oral controlled release | |
US11213505B2 (en) | Product based on iron bis-glycinate chelate and alginic acid and/or water-soluble salts thereof, formulations thereof, and pharmaceutical uses thereof | |
CN104204082B (en) | Producing high-molecular oxynitrides and the organic and inorganic heterozygosis compound of inorganic particle | |
RU2651042C1 (en) | Histochrome dosage form for oral administration and prolonged action | |
CN104434860A (en) | Ambroxol hydrochloride osmotic pump type pharmaceutical composition prepared by inclusion process | |
EP2371356B1 (en) | Multi-particle pharmaceutical formulation for colon absorption | |
US11865099B2 (en) | Product based on iron bis-glycinate chelate and alginic acid and/or water-soluble salts thereof, formulations thereof, and pharmaceutical uses thereof | |
JP6486349B2 (en) | Drug delivery | |
US11944633B2 (en) | Oral formulations of fasudil with ion exchange resin | |
CN112791189B (en) | High water-solubility 5-aminosalicylic acid pharmaceutical composition and preparation, preparation and application thereof | |
WO2008079818A2 (en) | Intravenous administration of water soluble analgesic formulations | |
Jain et al. | DEVELOPMENT AND EVALUATION OF TASTE MASKED ORALLY DISINTEGRATING TABLETS OF NORFLOXACIN | |
Yadav et al. | Formulation, Evaluation and Optimization of Fast-Dissolving Tablets Containing Nimesulide Micropellets | |
WO2024143197A1 (en) | Formulation and treatment method using same | |
JP4821607B2 (en) | Solid formulation with poorly water-soluble drug | |
CN116687843A (en) | High-stability buvaracetam solution, preparation method and application thereof | |
ITMI980078A1 (en) | ORAL FORMULATION WITH PROTRACT RELEASE OF POLYUNSATURATED FATTY ACIDS, IN PARTICULAR FOR THE RELEASE OF OMEGA 3 POLYUNSATURATED ACIDS |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2005822507 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2005327852 Country of ref document: AU |
|
WWE | Wipo information: entry into national phase |
Ref document number: 6009/DELNP/2007 Country of ref document: IN |
|
ENP | Entry into the national phase |
Ref document number: 2005327852 Country of ref document: AU Date of ref document: 20051219 Kind code of ref document: A |
|
WWP | Wipo information: published in national office |
Ref document number: 2005327852 Country of ref document: AU |
|
WWE | Wipo information: entry into national phase |
Ref document number: 11816308 Country of ref document: US |
|
WWE | Wipo information: entry into national phase |
Ref document number: 200580048186.7 Country of ref document: CN Ref document number: 2598364 Country of ref document: CA Ref document number: 2007555462 Country of ref document: JP |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1020077020070 Country of ref document: KR |
|
WWE | Wipo information: entry into national phase |
Ref document number: AP/P/2007/004156 Country of ref document: AP |
|
WWE | Wipo information: entry into national phase |
Ref document number: DZP2007000582 Country of ref document: DZ |
|
WWE | Wipo information: entry into national phase |
Ref document number: 200701735 Country of ref document: EA |
|
WWP | Wipo information: published in national office |
Ref document number: 2005822507 Country of ref document: EP |
|
WWW | Wipo information: withdrawn in national office |
Ref document number: 2005822507 Country of ref document: EP |
|
ENP | Entry into the national phase |
Ref document number: PI0520078 Country of ref document: BR Kind code of ref document: A2 |