WO1983003353A1 - Psyllium compositions - Google Patents
Psyllium compositions Download PDFInfo
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- WO1983003353A1 WO1983003353A1 PCT/US1982/000345 US8200345W WO8303353A1 WO 1983003353 A1 WO1983003353 A1 WO 1983003353A1 US 8200345 W US8200345 W US 8200345W WO 8303353 A1 WO8303353 A1 WO 8303353A1
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- WIPO (PCT)
- Prior art keywords
- psyllium
- polyethylene glycol
- water
- weight
- granules
- Prior art date
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/46—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes silicones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
- C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/68—Plantaginaceae (Plantain Family)
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1635—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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1641—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5005—Wall or coating material
- A61K9/5021—Organic macromolecular compounds
- A61K9/5026—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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5005—Wall or coating material
- A61K9/5021—Organic macromolecular compounds
- A61K9/5031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poly(lactide-co-glycolide)
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/42—Introducing metal atoms or metal-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/60—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which all the silicon atoms are connected by linkages other than oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
- C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C08G81/024—Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/16—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers in which all the silicon atoms are connected by linkages other than oxygen atoms
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/44—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes vinyl resins; acrylic resins
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/44—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes vinyl resins; acrylic resins
- H01B3/441—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes vinyl resins; acrylic resins from alkenes
Definitions
- This invention relates to granulated psyllium compositions which are readily dispersible in water and 5 aqueous beverages.
- Powdered husks of the psyllium seed. is a common and effective bulk laxative * drug.
- the hydrophilic properties of this natural fibrous laxative causes ingested doses to absorb large amounts of water, thus 10 producing bulk and normalizing regularity through proper stool formation.
- the single normal adult dose is about 3 grams of psyllium powder which is dispersed by the user in water or an aqueous beverage. Powdered psyllium has very poor 15 wetting capabilities and therefore must be vigorously mixed with aqueous fluids to produce a palatable dis ⁇ persion.
- psyllium seed preparations have been formulated to contain equal parts of active bulk laxative 20 and a sugar (usually dextrose) as a means of promoting dispersion ease. These 50:50 dilutions are also in ⁇ convenient to the user since mixability is still often difficult. Rigorous agitation and/or stirring are
- OMPI or potassium ion which preclude their use by diabetic patients and patients on low sodium diets.
- Pure psyllium powder resists wetting in water or aqueous beverages because of its fine particle size and the inability of water to penetrate the powder mass due to fast surface hydration and swelling. Vigorous agitation in water results in a lumpy dispersion. The lumps, although wetted on their outer surface, contain dry undispersed powder on the inside. Fluid penetration must precede hydration in order to accomplish instant wettability and dispersability.
- the wettability of powdered psyllium can be enhanced by diluting the particles with large amounts of a highly water soluble material, e.g., sucrose.
- a highly water soluble material e.g., sucrose.
- the water soluble material must impart dilation to the psyllium powder, viz., the creation of voids between the individual particles which hold them apart long enough to allow the individual particles to become wet rather than agglomerated into clumps.
- sugars have been used for this purpose with limited success. Effer ⁇ vescent sugar-psyllium mixtures self-dilate when carbon dioxide is released upon use. It follows therefore, that air alone should act as a diluent for a bed of psyllium if the bed were properly mechanically dilated.
- a wetting test was developed to show the effect of various polymers on the wettability of psyllium granules produced by wet granulation of psyllium powder with solutions thereof.
- the time required to completely wet 3.7 g of psyllium ladled onto the surface of 150 ml. of water (or aqueous beverage) in a 65 ml diameter beaker was measured. If greater than 2 minutes was required for wetting, the wetting time was recorded as greater than 120 seconds.
- Table I below lists the results of attempts to accomplish more rapid wetting of psyllium with glycerin, which theoretically should enhance dispersibility of the psyllium by increasing the surface wetting of the psyllium powder.
- Alcoholic (anhydrous ethanol) solutions of glycerin with or without Tween 80, a surface active agent, were added to psyllium powder. Thorough mixing of the wetted powder insured total distribution of the ingredients. The alcohol was evaporated, the powders were sized and tested. It was found that even when a strong wetting agent was added, glycerin did not enhance wettability.
- Table II below gives the wetting times obtained with various polymeric and other materials used to achieve mechanical dilation by wet granulation of the psyllium powder from an alcoholic (95% denatured) solu ⁇ tion of the selected material. Agglomeration of psyllium particles effectively achieved mechanical dila ⁇ tion by dilution with air voids. The concentrations thereof employed were dictated by the viscosity of the solutions thereof or toxicity considerations. Although dilation was accomplished in all cases except one (Pluronic a S.A.A.), fast aqueous penetration and uniform wetting was only occasionally achieved.
- Polyvinylpyrrolidone is one of the polymers which proved to be operable at concentrations above about 2%.
- U. S. 2,820,741 teaches the use of an alcoholic solution of PVP as a granulating agent for water-insoluble materials which are unstable in the presence of water and that PVP aids in the physical disintegration of granules when formed, into tablets or filled into capsules. However, it teaches nothing about the effect thereof upon the dispersibility of such granulated materials in water.
- U. S. 3,725,541 dis ⁇ closes the use of a water insoluble polymer or copolymer of vinylpyrrolidone and powdered sugar to produce a
- PEG is superior to PVP in achieving rapid dispersibility of the psyllium in water at concentrations above about 1.5% by weight of the psyllium.
- Patents which employ PEG in the preparation of pharmaceutical products are 2,638,822; 2,540,253; 3,308,217; 3,862,311; 3,932,613; and 4,151,273.
- Gakenheimer (2,540,253) discloses the use of PEG to form granules suitable for the preparation of tablets.
- Rieglman et al. (4,151,273) discloses a method of enhancing systemic absorption of poorly soluble drugs by forming a glossy solid matrix of the carrier (PEG) and the drug.
- a solution of the drug and the carrier is formed at an elevated temperature, with or without a solvent, and chilled rapidly to form a solid mass which can be ground to a powder.
- Leeson (3,862,311) discloses increased absorption of drugs when they are combined with carrier (PEG) and surfactant. See Col. 2, lines 3-9 and Col. 2, lines 48-58 for discussion of carriers used and of drug-surfact- ant-carrier ratios, respectively.
- Halpern et al. (2,698,822) disclose PEG used to increase systemic absorption of insoluble drugs.
- Lowry et al. (3,308,217) disclose a dry granulation method of preparing a mix for producing tablets using PEG (See Col. 4, lines 36-44) , which employs a heating step.
- Chapura (3,932,613) claims a PEG suppository.
- this invention relates to ingestible granulated psyllium compositions consisting essentially of granules of psyllium powder rendered rapidly dispersible in water by the presence on the surface of the psyllium particles of a coating of an amount of a non-toxic, normally solid, alcohol soluble water dispersible polyethylene glycol, polyvinyl- pyrrolidone, or mixture thereof, effective to render the psyllium particles substantially instantly and uniformly dispersible in water.
- the coating consists predominantly of polyethylene glycol plus an amount of polyvinyl pyrrolidone effective to reduce the friability of the granules.
- this invention relates to a method for rendering ingestible psyllium powder sub ⁇ stantially instantly and uniformly dispersible in water which comprises wet granulating the psyllium powder with an amount of a solution in a volatile organic sol ⁇ vent, or mixture thereof with water, of a non-toxic, normally solid, alcohol soluble water dispersible poly ⁇ ethylene glycol, polyvinylpyrrolidone, or both, effective to render the granules when dry substantially instantly and uniformly dispersible in water.
- the solvent is anhydrous ethanol.
- the psyllium powders employed in this invention are the conventional powders used commercially as such and to produce the prior art granulated compositions described hereinbefore.
- wet granulation process of this invention employs procedures well-known in the art. See e.g., U. ' S. 2,820,741 and references cited therein; 2,540,253; 2,980,589; and Newitt, D. M. et al. Proc. Fert. Soc, 1960, No. 55, pp. 1-35.
- the polymers employed in this invention are the non-toxic, normally solid (under ambient conditions) alcohol soluble, water dispersible polymers of ethylene
- polystyrene glycol and of vinylpyrrolidone Such polymers are well-known in the art. Such polyethylene glycols have somewhat lower molecular weights than the polyvinyl- pyrrolidones having substantially the same solubilities.
- the commercially available polyethylene glycols having the desired properties have molecular weights ranging from about 900 to about 20,000.
- the normally liquid polymers having lower molecular weights are less effective than the normally solid polymers. Preferred are those having a molecular weight from about 3,000 to 8,000.
- a particularly useful polymer has an average molecular weight of about 3,350. Included in the poly ⁇ ethylene glycols which can be employed in this invention are those whose terminal hydroxy groups have been chemically modified, e.g., by an ether or ester group. The commercially available polyvinylpyrrolidones having the desired properties have molecular weights ranging from about 10,000 to 360,000. A particularly useful polymer (Povidone K29/32) has a molecular weight of about 40,000. Contemplated equivalents of these polymers are corresponding copolymers and terpolymers having substantially the same physical characteristics.
- the polyethylene glycols for the most part are superior to the polyvinylpyrrolidones in their ability to produce psyllium granules which are sub ⁇ stantially instantly wettable, i.e., which are completely wetted within 10 seconds in the wetting test described hereinafter. Therefore, the coating on the psyllium particles of the preferred compositions of this invention comprise and more preferably consist predominantly, i.e., more than 50% by weight, and most preferably consist of about 65-100% by weight, of polyethylene glycol.
- psyllium granules coated solely with PEG have the fastest wetting times, the granules are rather frangible and tend to break up with handling or shipping.
- the coating consists of a minor proportion, i.e., less than 50%, preferably about 10-35%, and most preferably about 15-25%, e.g., about 20%, of PVP, friability is reduced substantially without significantly affecting wettability rates.
- the amount of PEG, PVP or mixture thereof present in the compositions of this invention varies somewhat with the particular polymers employed. Usually, however, 5% by weight of the granulated compositions is sufficient to impart substantially instantaneous, i.e., within 10 seconds, water wettability to the psyllium granules. Higher percentages ordinarily impart no further benefits to the compositions. The minimum amount required to do so ordinarily is at least 2%. As would be expected, minor amounts of other poly ⁇ mers or other ingredients in the coating of the compositions can be tolerated without destroying the operability of the coating in rendering the psyllium granules substantially instantly and uniformly dis- persible in water.
- the granulated psyllium compositions of this invention consist substantially entirely, i.e., at least about 90%, preferably about 92.5 - 97.5%, e.g., about 95%, by weight, of powdered psyllium.
- the starting psyllium powder is wet granulated with a vola- tile organic solvent, e.g., the lower alkanols, e.g., methanol, ethanol, isopropanol and n-butanol, ketones, e.g., acetone and methylethyl ketone, ethers and esters.
- a vola- tile organic solvent e.g., the lower alkanols, e.g., methanol, ethanol, isopropanol and n-butanol, ketones, e.g., acetone and methylethyl ketone, ethers and esters.
- ethanol or 95% ethanol and 5% methanol is preferred.
- Substantially anhydrous solvents i.e., no more than about 10% water, are preferred because the presence of a significant proportion
- OMPI of water tends to have an adverse effect on the drying times and/or the wettability of the psyllium granules produced therefrom, generally directly proportion to the amount of water in the solvent.
- an amount of water in the organic solvent which does not significantly transfer from the solvent phase to the psyllium e.g., up to about 50% by volume but preferably less than 25% by volume, generally can be tolerated in the solvent without seriously affecting the water dispersibility of the psyllium granules produced therefrom.
- the amount of solvent employed is preferably only that amount required to uniformly wet the psyllium particles, e.g., from about 5% to 25%, preferably about 7-15%, by weight thereof. Larger amounts of solvent have no advantage and tend to complicate the wet granulation process. Lesser amounts tend to wet the psyllium particles unevenly, producing granules which produce lumps when dispersed in water.
- the proportion of polymer or mixture of polymers to solvent employed in the wet granulation process depends primarily upon the amount of polymer desired to be deposited on the polymers, assuming an amount of solvent in excess of that required to wet the psyllium is not employed. Generally, a solvent to polymer ratio from about 3:1 to 1:1, preferably about 2:1, by weight is employed.
- the psyllium powder is then wet granulated in a conventional manner with an amount of the polymer solution sufficient to uniformly wet the psyllium par ⁇ ticles and to deposit thereon the desired amount of polymer or mixture of polymers, viz., by gradually adding the solution to the psyllium powder with con ⁇ tinuous agitation.
- the thus-produced wet granules are dried of solvent, preferably without agitation, e.g., in trays in a drying room with exhaust fans to discharge the evaporated solvent.
- the granules can then be screened to desired particle size distribution, e.g., through a No. 20 mesh screen.
- the dry granulated particles can then be packaged conventionally, e.g., unit dose pouches or 25 g. bottles.
- the granulated psyllium compositions of this invention can readily be dispersed in aqueous beverages, e.g., prune juice, tomato juice, orange and other fruit juices, fruit flavored soft drinks, milk, coffee and tea, the limitations being dictated primarily by palatability considerations rather than rapid dispersibility.
- the granulated psyllium compositions were produced from 475 g of powdered psyllium seed husks and a solution of powdered polyethylene glycol of an average molecular weight of 3,350 (P.E.G.
- Wettability of the dry granules was determined according to the wetting test described above. Fri ⁇ ability of the dry granules was determined on a Cenco Meinzer Sieve Shaker (speed No. 4) containing 535 glass beads each weighing about 0.17 g. and having a diameter of 0.195 inch. 80 grams of the dry granules retained on a 60 mesh screen were placed on the 60 mesh screen along with the glass beads and the shaker run for either 2 or 4 minutes and the percentage of under 60 mesh granules determined.
- the preceding examples can be repeated with similar success by substituting the generically or specifically described reactants and/or operating conditions of this invention for those used in the preceding examples.
Abstract
Psyllium powder is rendered substantially instantly and uniformly dispersible in water by wetting the psyllium particles with an alcoholic solution of at least one of polyethylene glycol and polyvinylpyrrolidone and granulating the thus-coated particles. Polyvinylpyrrolidine in the coating reduces the friability of the granules.
Description
PSYLLIUM COMPOSITIONS
Background of the Invention
This invention relates to granulated psyllium compositions which are readily dispersible in water and 5 aqueous beverages.
Powdered husks of the psyllium seed. is a common and effective bulk laxative*drug. The hydrophilic properties of this natural fibrous laxative causes ingested doses to absorb large amounts of water, thus 10 producing bulk and normalizing regularity through proper stool formation.
The single normal adult dose is about 3 grams of psyllium powder which is dispersed by the user in water or an aqueous beverage. Powdered psyllium has very poor 15 wetting capabilities and therefore must be vigorously mixed with aqueous fluids to produce a palatable dis¬ persion.
Historically, psyllium seed preparations have been formulated to contain equal parts of active bulk laxative 20 and a sugar (usually dextrose) as a means of promoting dispersion ease. These 50:50 dilutions are also in¬ convenient to the user since mixability is still often difficult. Rigorous agitation and/or stirring are
** required to render the composition palatable and lump 25 free. Moreover, patients on restricted sugar-free or weight controlling diets cannot normally use these.products.
Attempts to improve mixability have led to effer¬ vescent powder formulas which at best still contain only about 50% of active bulk laxative, are usually high in 30 sugar content and contain significant amounts of sodium
OMPI
or potassium ion, which preclude their use by diabetic patients and patients on low sodium diets.
Pure psyllium powder resists wetting in water or aqueous beverages because of its fine particle size and the inability of water to penetrate the powder mass due to fast surface hydration and swelling. Vigorous agitation in water results in a lumpy dispersion. The lumps, although wetted on their outer surface, contain dry undispersed powder on the inside. Fluid penetration must precede hydration in order to accomplish instant wettability and dispersability.
The wettability of powdered psyllium can be enhanced by diluting the particles with large amounts of a highly water soluble material, e.g., sucrose. The disadvantages of doing so have been discussed above. Moreover, lumping is not totally avoided because in order to do so, the water soluble material must impart dilation to the psyllium powder, viz., the creation of voids between the individual particles which hold them apart long enough to allow the individual particles to become wet rather than agglomerated into clumps. As stated above, sugars have been used for this purpose with limited success. Effer¬ vescent sugar-psyllium mixtures self-dilate when carbon dioxide is released upon use. It follows therefore, that air alone should act as a diluent for a bed of psyllium if the bed were properly mechanically dilated.
However, neither dilation alone nor the water solubili of the coating agent ensures rapid and complete dispersi- bility of powdered psyllium in water and aqueous beverages. Although a number of water soluble or dispersible polymers can be used to achieve dilation of powdered psyllium by conversion thereof into granules in which the psyllium particles are diluted with air voids, instant and complete dispersibility of the resulting product in water and aqueous beverages is rarely achieved
employing amounts thereof which could form alcoholic solutions of a viscosity low enough to be used to granulate the psyllium. A wetting test was developed to show the effect of various polymers on the wettability of psyllium granules produced by wet granulation of psyllium powder with solutions thereof. The time required to completely wet 3.7 g of psyllium ladled onto the surface of 150 ml. of water (or aqueous beverage) in a 65 ml diameter beaker was measured. If greater than 2 minutes was required for wetting, the wetting time was recorded as greater than 120 seconds.
Table I below lists the results of attempts to accomplish more rapid wetting of psyllium with glycerin, which theoretically should enhance dispersibility of the psyllium by increasing the surface wetting of the psyllium powder. Alcoholic (anhydrous ethanol) solutions of glycerin with or without Tween 80, a surface active agent, were added to psyllium powder. Thorough mixing of the wetted powder insured total distribution of the ingredients. The alcohol was evaporated, the powders were sized and tested. It was found that even when a strong wetting agent was added, glycerin did not enhance wettability. Only with equal parts of psyllium and dextrose did a mixture of glycerin and wetting agent produce fast wetting because although glycerin should have been a good wetting bridge between psyllium and water, it did not impart any dilation to the powder mass. In fact, the quick hydration at the powder-water inter¬ face actually impeded penetration of the water and complete wetting of all the particles was prevented. By dilution with 50% dextrose, dilation of the psyllium in effect was accomplished and penetration of the water preceded hydration and, with the aid of the glycerin and wetting agent, fast lump-free wetting occurred. However, the resulting product had the other disadvantages discussed abo
- TJILE_
TABLE I
Contents. % Weiαting
Tilne
Psyllium Dextrose Glycerin Tween 80 (s. _ιC.)
50 50 —,_ > 120
50 48.4 1.5 0.1 10
75 23.4 1.5 0.1 > 120
98.4 0 1.5 0.1 > 120
96.9 3.0 0.1 > 120
97.9 _.— 2.0 0.1 > 120
97.0 3.0 _.— > 120
95.0 5.0 > 120
Table II below gives the wetting times obtained with various polymeric and other materials used to achieve mechanical dilation by wet granulation of the psyllium powder from an alcoholic (95% denatured) solu¬ tion of the selected material. Agglomeration of psyllium particles effectively achieved mechanical dila¬ tion by dilution with air voids. The concentrations thereof employed were dictated by the viscosity of the solutions thereof or toxicity considerations. Although dilation was accomplished in all cases except one (Pluronic a S.A.A.), fast aqueous penetration and uniform wetting was only occasionally achieved.
TABLE II
Psyllium Wetting Content Polymer Time
100% None > 120 98% Methocel E-15 2% > 120 99.8% Carbopol 0.2% > 120 99% Methocel E-5 1% 90 99% Pluronic F-68 1% > 120 99% Gantrez - AN119 1. > 120 98% Xanthan Gum 2% > 120 95% Sucrose Syrup 5% > 120 99% VP 1% 22 99% PEG 1% (3350) 30
Notwithstanding the foregoing results, we have found that certain of the foregoing polymers can be employed in a wet granulation process at higher con¬ centrations to produce granulated psyllium products which not only have a high psyllium content (greater than 90% and usually at least about 95%) but which are substantially instantly and uniformly dispersible in water and aqueous beverages.
Polyvinylpyrrolidone (PVP) is one of the polymers which proved to be operable at concentrations above about 2%. U. S. 2,820,741 teaches the use of an alcoholic solution of PVP as a granulating agent for water-insoluble materials which are unstable in the presence of water and that PVP aids in the physical disintegration of granules when formed, into tablets or filled into capsules. However, it teaches nothing about the effect thereof upon the dispersibility of such granulated materials in water. U. S. 3,725,541 dis¬ closes the use of a water insoluble polymer or copolymer of vinylpyrrolidone and powdered sugar to produce a
_OMPI
anti-diarrhea product. Other patents which disclose a process of preparing a pharmaceutical by the addition of the active ingredient to an alcoholic PVP solution are 3,089,818; 3,257,277; 3,553,313; 3,673,163; and 4,081,529. We have also found that polyethylene glycol
(PEG) is superior to PVP in achieving rapid dispersibility of the psyllium in water at concentrations above about 1.5% by weight of the psyllium. Patents which employ PEG in the preparation of pharmaceutical products are 2,638,822; 2,540,253; 3,308,217; 3,862,311; 3,932,613; and 4,151,273. Gakenheimer (2,540,253) discloses the use of PEG to form granules suitable for the preparation of tablets. Rieglman et al. (4,151,273) discloses a method of enhancing systemic absorption of poorly soluble drugs by forming a glossy solid matrix of the carrier (PEG) and the drug. A solution of the drug and the carrier is formed at an elevated temperature, with or without a solvent, and chilled rapidly to form a solid mass which can be ground to a powder. Leeson (3,862,311) discloses increased absorption of drugs when they are combined with carrier (PEG) and surfactant. See Col. 2, lines 3-9 and Col. 2, lines 48-58 for discussion of carriers used and of drug-surfact- ant-carrier ratios, respectively. Halpern et al. (2,698,822) disclose PEG used to increase systemic absorption of insoluble drugs. Lowry et al. (3,308,217) disclose a dry granulation method of preparing a mix for producing tablets using PEG (See Col. 4, lines 36-44) , which employs a heating step. Chapura (3,932,613) claims a PEG suppository.
Summary of the Invention
In a composition aspect, this invention relates to ingestible granulated psyllium compositions consisting essentially of granules of psyllium powder rendered
rapidly dispersible in water by the presence on the surface of the psyllium particles of a coating of an amount of a non-toxic, normally solid, alcohol soluble water dispersible polyethylene glycol, polyvinyl- pyrrolidone, or mixture thereof, effective to render the psyllium particles substantially instantly and uniformly dispersible in water. In a preferred aspect, the coating consists predominantly of polyethylene glycol plus an amount of polyvinyl pyrrolidone effective to reduce the friability of the granules.
In a method aspect, this invention relates to a method for rendering ingestible psyllium powder sub¬ stantially instantly and uniformly dispersible in water which comprises wet granulating the psyllium powder with an amount of a solution in a volatile organic sol¬ vent, or mixture thereof with water, of a non-toxic, normally solid, alcohol soluble water dispersible poly¬ ethylene glycol, polyvinylpyrrolidone, or both, effective to render the granules when dry substantially instantly and uniformly dispersible in water. In a preferred aspect, the solvent is anhydrous ethanol.
Detailed Discussion
The psyllium powders employed in this invention are the conventional powders used commercially as such and to produce the prior art granulated compositions described hereinbefore.
Similarly, the wet granulation process of this invention employs procedures well-known in the art. See e.g., U.' S. 2,820,741 and references cited therein; 2,540,253; 2,980,589; and Newitt, D. M. et al. Proc. Fert. Soc, 1960, No. 55, pp. 1-35.
The polymers employed in this invention are the non-toxic, normally solid (under ambient conditions) alcohol soluble, water dispersible polymers of ethylene
glycol and of vinylpyrrolidone. Such polymers are well-known in the art. Such polyethylene glycols have somewhat lower molecular weights than the polyvinyl- pyrrolidones having substantially the same solubilities. The commercially available polyethylene glycols having the desired properties have molecular weights ranging from about 900 to about 20,000. The normally liquid polymers having lower molecular weights are less effective than the normally solid polymers. Preferred are those having a molecular weight from about 3,000 to 8,000.
A particularly useful polymer (PEG 3350) has an average molecular weight of about 3,350. Included in the poly¬ ethylene glycols which can be employed in this invention are those whose terminal hydroxy groups have been chemically modified, e.g., by an ether or ester group. The commercially available polyvinylpyrrolidones having the desired properties have molecular weights ranging from about 10,000 to 360,000. A particularly useful polymer (Povidone K29/32) has a molecular weight of about 40,000. Contemplated equivalents of these polymers are corresponding copolymers and terpolymers having substantially the same physical characteristics.
Surprisingly, the polyethylene glycols for the most part are superior to the polyvinylpyrrolidones in their ability to produce psyllium granules which are sub¬ stantially instantly wettable, i.e., which are completely wetted within 10 seconds in the wetting test described hereinafter. Therefore, the coating on the psyllium particles of the preferred compositions of this invention comprise and more preferably consist predominantly, i.e., more than 50% by weight, and most preferably consist of about 65-100% by weight, of polyethylene glycol.
Although psyllium granules coated solely with PEG have the fastest wetting times, the granules are rather frangible and tend to break up with handling or shipping.
When the coating consists of a minor proportion, i.e., less than 50%, preferably about 10-35%, and most preferably about 15-25%, e.g., about 20%, of PVP, friability is reduced substantially without significantly affecting wettability rates.
The amount of PEG, PVP or mixture thereof present in the compositions of this invention varies somewhat with the particular polymers employed. Usually, however, 5% by weight of the granulated compositions is sufficient to impart substantially instantaneous, i.e., within 10 seconds, water wettability to the psyllium granules. Higher percentages ordinarily impart no further benefits to the compositions. The minimum amount required to do so ordinarily is at least 2%. As would be expected, minor amounts of other poly¬ mers or other ingredients in the coating of the compositions can be tolerated without destroying the operability of the coating in rendering the psyllium granules substantially instantly and uniformly dis- persible in water. However, such other materials do not ordinarily impart any benefits to the compositions and usually have an adverse effect thereon. Therefore, their presence therein is not ordinarily desirable. The granulated psyllium compositions of this invention consist substantially entirely, i.e., at least about 90%, preferably about 92.5 - 97.5%, e.g., about 95%, by weight, of powdered psyllium.
In carrying out the method of this invention, the starting psyllium powder is wet granulated with a vola- tile organic solvent, e.g., the lower alkanols, e.g., methanol, ethanol, isopropanol and n-butanol, ketones, e.g., acetone and methylethyl ketone, ethers and esters. Because of residue problems, ethanol or 95% ethanol and 5% methanol is preferred. Substantially anhydrous solvents, i.e., no more than about 10% water, are preferred because the presence of a significant proportion
OMPI
of water tends to have an adverse effect on the drying times and/or the wettability of the psyllium granules produced therefrom, generally directly proportion to the amount of water in the solvent. However, an amount of water in the organic solvent which does not significantly transfer from the solvent phase to the psyllium, e.g., up to about 50% by volume but preferably less than 25% by volume, generally can be tolerated in the solvent without seriously affecting the water dispersibility of the psyllium granules produced therefrom.
The amount of solvent employed is preferably only that amount required to uniformly wet the psyllium particles, e.g., from about 5% to 25%, preferably about 7-15%, by weight thereof. Larger amounts of solvent have no advantage and tend to complicate the wet granulation process. Lesser amounts tend to wet the psyllium particles unevenly, producing granules which produce lumps when dispersed in water. The proportion of polymer or mixture of polymers to solvent employed in the wet granulation process depends primarily upon the amount of polymer desired to be deposited on the polymers, assuming an amount of solvent in excess of that required to wet the psyllium is not employed. Generally, a solvent to polymer ratio from about 3:1 to 1:1, preferably about 2:1, by weight is employed.
The psyllium powder is then wet granulated in a conventional manner with an amount of the polymer solution sufficient to uniformly wet the psyllium par¬ ticles and to deposit thereon the desired amount of polymer or mixture of polymers, viz., by gradually adding the solution to the psyllium powder with con¬ tinuous agitation. When all of the solution has been added, the thus-produced wet granules are dried of solvent, preferably without agitation, e.g., in trays
in a drying room with exhaust fans to discharge the evaporated solvent. If desired, the granules can then be screened to desired particle size distribution, e.g., through a No. 20 mesh screen. The dry granulated particles can then be packaged conventionally, e.g., unit dose pouches or 25 g. bottles.
In addition to being substantially instantly and uniformly dispersible in water, the granulated psyllium compositions of this invention can readily be dispersed in aqueous beverages, e.g., prune juice, tomato juice, orange and other fruit juices, fruit flavored soft drinks, milk, coffee and tea, the limitations being dictated primarily by palatability considerations rather than rapid dispersibility. Without further elaboration, it is believed that one skilled in the art can, using the preceding description, utilize the present invention to its fullest extent. The following preferred specific embodiments are, therefore, to be construed as merely illustrative and not limitative of the remainder of the disclosure in any way whatsoever.
EXAMPLE I
5.331 kg of powdered polyvinylpyrrolidone (Povidone K29/32) and 21.613 kg of powdered polyethylene glycol (P.E.G. 3350) was dissolved in 50 kg of anhydrous 95% ethanol/5% methanol with warming to 50° C. until the polymers dissolved therein. The solution was pumped onto 500 kg of tumbling psyllium powder. The wet granules which formed were, spread onto drying trays, where they were dried overnight. Screening the dry granules through a No. 14 mesh screen yielded a uniform essentially powder-free granulated product which resists crumbling during shipping and handling and which rapidly (in less than 10 seconds) disperses without lumping in water.
O PI
EXAMPLE II
In the examples which follow, unless indicated otherwise, the granulated psyllium compositions were produced from 475 g of powdered psyllium seed husks and a solution of powdered polyethylene glycol of an average molecular weight of 3,350 (P.E.G. 3350) and/or polyvinylpyrrolidone of an average molecular weight of 40,000 ("Povidone K29/32") , in 60 ml anhydrous ethanol denatured with 5% w/w methanol (SDA-3A) by dissolving the polymer in the ethanol with heating, charging the powdered psyllium in a Hobart mixer; wet granulating by gradually adding the polymer solution to the psyllium while the latter is agitated in the mixer and mixing for one minute; spreading the wet granules out on a tray and drying overnight at room temperature and sizing the dried granules through No. 20 mesh screen.
Wettability of the dry granules was determined according to the wetting test described above. Fri¬ ability of the dry granules was determined on a Cenco Meinzer Sieve Shaker (speed No. 4) containing 535 glass beads each weighing about 0.17 g. and having a diameter of 0.195 inch. 80 grams of the dry granules retained on a 60 mesh screen were placed on the 60 mesh screen along with the glass beads and the shaker run for either 2 or 4 minutes and the percentage of under 60 mesh granules determined.
The preceding examples can be repeated with similar success by substituting the generically or specifically described reactants and/or operating conditions of this invention for those used in the preceding examples.
From the foregoing description, one skilled in the art can easily ascertain the essential characteristics of this invention, and without departing from the spirit and scope thereof, can make various changes and modifications of the invention to adapt it to various usages and conditions.
Claims
1. An ingestible granulated psyllium composition consisting essentially of granules of psyllium powder, characterized in that the psyllium is rendered sub¬ stantially instantly and uniformly dispersible in water by the presence on the surface of the psyllium particles of a coating of an amount from up to about 10% by weight of a non-toxic, normally solid, alcohol soluble, water dispersible polyethylene glycol, polyvinylpyrrolidone, or mixture thereof.
2. A composition according to Claim 1 wherein the coating comprises polyethylene glycol.
3. A composition according to Claim 1 whose coating consists predominantly of about 2 to about 5% by weight of the composition of polyethylene glycol.
4. A composition according to Claim 2 wherein the polyethylene glycol has a molecular weight from about 3,000 to 8,000.
5. A composition according to Claim 2 wherein the coating on the psyllium particles contains an amount of polyvinylpyrrolidone effective to render the granules significantly less friable than correspondingly granulated psyllium coated with the same amount of the polyethylene glycol only.
6. A composition according to Claim 5 containing about 2.5 to 4% by weight thereof of a polyethylene glycol and about 2 to 0.5% by weight thereof of polyvinyl¬ pyrrolidone. 16
7. A composition according to Claim 6 wherein the polyethylene glycol has a molecular weight from about 3,000 to about 8,000.
8. A composition according to Claim 7 containing about 4% by weight of polyethylene glycol and about 1% by weight of polyvinylpyrrolidone.
9. A composition according to Claim 8 wherein the polyethylene glycol has a molecular weight of about 3,350.
10. A method for producing an ingestible granulated psyllium composition according to Claim 1, characterized in that psyllium powder is wet granulated with an amount of a solution in a volatile organic solvent, or mixture thereof with water, of up to 10% by weight of the psyllium of a non-toxic, normally solid, alcohol soluble, water dispersible polyethylene glycol, polyvinyl¬ pyrrolidone, or both, effective to render the psyllium granules when dry substantially instantly and uniformly dispersible in water.
11. A method according to Claim 10 wherein the solvent is anhydrous.
12. A method according to Claim 10 wherein the solvent consists at least about 95% of ethanol.
13. A method according to Claim 10 wherein the solution comprises polyethylene glycol.
14. A method according to Claim 13 wherein the solution also contains an amount of polyvinylpyrrolidone effective to render the granules less friable than corresponding granules produced from a solution of the same amount of the polyethylene glycol alone.
15. A method according to Claim 13 wherein the solvent is anhydrous.
16. A method according to Claim 15 wherein the solvent consists at least about 95% of ethanol.
Priority Applications (32)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/207,600 US4321263A (en) | 1980-09-30 | 1980-11-17 | Psyllium compositions |
GR66152A GR75020B (en) | 1980-09-30 | 1981-09-15 | |
ZA816715A ZA816715B (en) | 1980-09-30 | 1981-09-25 | Production of silane modified copolymers of alkylene-alkyl acrylates,polysiloxanes having combined therein organo titanates and the use thereof in the production of silane modified copolymers of alkylene-alkyl acrylates |
CA000386696A CA1176782A (en) | 1980-09-30 | 1981-09-25 | Production of silane modified copolymers of alkylene- alkyl acrylates, polysiloxanes having combined therein organo titanates and the use thereof in the production of silane modified copolymers of alkylene- alkyl acylates |
IL63927A IL63927A0 (en) | 1980-09-30 | 1981-09-25 | Production of silane modified copolymers of alkylene-alkyl acrylates,polysiloxanes having combined therein organo-titanates and the use thereof in the production of silane modified copolymers of alkylenealkyl acrylates |
NO813288A NO813288L (en) | 1980-09-30 | 1981-09-28 | PREPARATION OF SILANE-MODIFIED COPOLYMERS OF ALKYLENE-ALKYLACRYLATES, POLYSILOXANES WITH THIRD ORGANOTITANATES AND THE USE OF THESE IN PREPARATION |
ES505873A ES8205828A1 (en) | 1980-09-30 | 1981-09-29 | Production of silane modified copolymers of alkylene-alkyl acrylates, polysiloxanes having combined therein organo titanates used in their production, process for producing such polysiloxanes, and electrical conductors insulated by cured silane modified copolymers. |
JP56153127A JPS57126804A (en) | 1980-09-30 | 1981-09-29 | Manufacture of silane-modified alkylene- acrylic acid alkyl copolymer, organotitanate- bonded polysiloxanes and use for manufacture of silane-modified alkylene-acrylic acid alkyl copolymer |
DE8181304496T DE3173770D1 (en) | 1980-09-30 | 1981-09-29 | Production of silane modified copolymers of alkylene-alkyl acrylates, polysiloxanes having combined therein organo titanates used in their production, process for producing such polysiloxanes, and electrical conductors insulated by cured silane modified copolymers |
EP83111039A EP0107211A3 (en) | 1980-09-30 | 1981-09-29 | Polysiloxanes and process for preparing same |
KR1019810003658A KR860001033B1 (en) | 1980-09-30 | 1981-09-29 | Production of silane modified copolymers of alkylene alkyl acrylates |
AU75746/81A AU549650B2 (en) | 1980-09-30 | 1981-09-29 | Polysiloxanes containing organic titanates |
DK430381A DK430381A (en) | 1980-09-30 | 1981-09-29 | METHOD OF PREPARING SILANE MODIFIED COPOLYMERS OF ALKYLEN-ALKYL ACRYLATES |
IN1091/CAL/81A IN155681B (en) | 1980-09-30 | 1981-09-29 | |
BR8106256A BR8106256A (en) | 1980-09-30 | 1981-09-29 | PROCESS FOR THE PRODUCTION OF A POLYSILOXAN COPOLIMER AND PROCESS FOR ITS PRODUCTION |
CS817131A CS713181A2 (en) | 1980-09-30 | 1981-09-29 | Zpusob vyroby ve vode tvrditelnych, silanem modifikovanych alkylen alkyl akrylatovych kopolymeru |
EP81304496A EP0049155B1 (en) | 1980-09-30 | 1981-09-29 | Production of silane modified copolymers of alkylene-alkyl acrylates, polysiloxanes having combined therein organo titanates used in their production, process for producing such polysiloxanes, and electrical conductors insulated by cured silane modified copolymers |
FI813049A FI813049L (en) | 1980-09-30 | 1981-09-30 | ALKYLENE-ALKYL-AKRYLATER POLYSILOXANER I ALKYL ORGANO-TITANATER OCH ANVAENDNING AV DESSA VID FRAMSTAELLNING AV SILYMODIFIERADE COPOLYMERER AV ALYYLEN-ALK |
PL1981233254A PL129360B1 (en) | 1980-09-30 | 1981-09-30 | Process for manufacturing copolymers of alkylenes with silanmodified alkyl acrylates |
AR288783A AR229176A1 (en) | 1980-09-30 | 1982-03-17 | METHOD FOR PRODUCING AN INGERIBLE COMPOSITION OF GRANULATED PSYLLIUM |
IT20240/82A IT1150693B (en) | 1980-09-30 | 1982-03-18 | Rapidly water-dispersible psyllium compsn. |
ES510650A ES8400875A1 (en) | 1980-09-30 | 1982-03-22 | Production of silane modified copolymers of alkylene-alkyl acrylates, polysiloxanes having combined therein organo titanates used in their production, process for producing such polysiloxanes, and electrical conductors insulated by cured silane modified copolymers. |
EP82901260A EP0104167B1 (en) | 1980-09-30 | 1982-03-22 | Psyllium compositions |
DE8282901260T DE3280057D1 (en) | 1980-09-30 | 1982-03-22 | PSYLLIUM COMPOSITIONS. |
JP57501316A JPS59500417A (en) | 1980-09-30 | 1982-03-22 | Car maeko composition |
ES510639A ES510639A0 (en) | 1980-09-30 | 1982-03-22 | PROCEDURE FOR PREPARING MODISED POLYSILOXANES WITH ORGANOTITANATES. |
PCT/US1982/000345 WO1983003353A1 (en) | 1980-09-30 | 1982-03-22 | Psyllium compositions |
NZ200489A NZ200489A (en) | 1980-09-30 | 1982-04-30 | Granulated psyllium composition readily dispersible in water |
AU83199/82A AU551220B2 (en) | 1980-09-30 | 1982-05-03 | Psyllium compositions |
DK498383A DK498383A (en) | 1980-09-30 | 1983-10-31 | PSYLLIUM PREPARATIONS |
NO834266A NO834266L (en) | 1980-09-30 | 1983-11-21 | PSYLLIUMPREPARATER |
JP59030480A JPS6035027A (en) | 1980-09-30 | 1984-02-22 | Polysiloxane bonded with organotitanate |
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/192,319 US4328323A (en) | 1979-08-29 | 1980-09-30 | Production of silane modified copolymers of alkylene-alkyl acrylates |
US06/207,600 US4321263A (en) | 1980-09-30 | 1980-11-17 | Psyllium compositions |
AR288783A AR229176A1 (en) | 1980-09-30 | 1982-03-17 | METHOD FOR PRODUCING AN INGERIBLE COMPOSITION OF GRANULATED PSYLLIUM |
IT20240/82A IT1150693B (en) | 1980-09-30 | 1982-03-18 | Rapidly water-dispersible psyllium compsn. |
ES510650A ES8400875A1 (en) | 1980-09-30 | 1982-03-22 | Production of silane modified copolymers of alkylene-alkyl acrylates, polysiloxanes having combined therein organo titanates used in their production, process for producing such polysiloxanes, and electrical conductors insulated by cured silane modified copolymers. |
PCT/US1982/000345 WO1983003353A1 (en) | 1980-09-30 | 1982-03-22 | Psyllium compositions |
NZ200489A NZ200489A (en) | 1980-09-30 | 1982-04-30 | Granulated psyllium composition readily dispersible in water |
Publications (1)
Publication Number | Publication Date |
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WO1983003353A1 true WO1983003353A1 (en) | 1983-10-13 |
Family
ID=36764430
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1982/000345 WO1983003353A1 (en) | 1980-09-30 | 1982-03-22 | Psyllium compositions |
Country Status (22)
Country | Link |
---|---|
US (1) | US4321263A (en) |
EP (3) | EP0049155B1 (en) |
JP (3) | JPS57126804A (en) |
KR (1) | KR860001033B1 (en) |
AR (1) | AR229176A1 (en) |
AU (2) | AU549650B2 (en) |
BR (1) | BR8106256A (en) |
CA (1) | CA1176782A (en) |
CS (1) | CS713181A2 (en) |
DE (2) | DE3173770D1 (en) |
DK (2) | DK430381A (en) |
ES (3) | ES8205828A1 (en) |
FI (1) | FI813049L (en) |
GR (1) | GR75020B (en) |
IL (1) | IL63927A0 (en) |
IN (1) | IN155681B (en) |
IT (1) | IT1150693B (en) |
NO (2) | NO813288L (en) |
NZ (1) | NZ200489A (en) |
PL (1) | PL129360B1 (en) |
WO (1) | WO1983003353A1 (en) |
ZA (1) | ZA816715B (en) |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0168360A2 (en) * | 1984-06-29 | 1986-01-15 | Roberto Valducci | Process for preparing etofibrate or similar compounds containing sustained release microgranules and products thus obtained |
EP0168360A3 (en) * | 1984-06-29 | 1987-01-07 | Roberto Valducci | Process for preparing etofibrate or similar compounds containing sustained release microgranules and products thus obtained |
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