Classifications

• • 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
  • A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
  • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
  • A23D7/003—Compositions other than spreads
• • A—HUMAN NECESSITIES
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  • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
  • A61K31/047—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates having two or more hydroxy groups, e.g. sorbitol
• • A—HUMAN NECESSITIES
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  • A61K31/12—Ketones
  • A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
• • A—HUMAN NECESSITIES
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  • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
  • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
  • A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
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  • A61K31/33—Heterocyclic compounds
  • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
  • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
  • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
• • A—HUMAN NECESSITIES
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  • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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  • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
  • A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
  • A61K35/56—Materials from animals other than mammals
  • A61K35/60—Fish, e.g. seahorses; Fish eggs
• • A—HUMAN NECESSITIES
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  • 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)
• • A—HUMAN NECESSITIES
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  • 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)
  • A61K36/28—Asteraceae or Compositae (Aster or Sunflower family), e.g. chamomile, feverfew, yarrow or echinacea
• • A—HUMAN NECESSITIES
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  • A61K36/18—Magnoliophyta (angiosperms)
  • A61K36/185—Magnoliopsida (dicotyledons)
  • A61K36/48—Fabaceae or Leguminosae (Pea or Legume family); Caesalpiniaceae; Mimosaceae; Papilionaceae
• • A—HUMAN NECESSITIES
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  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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  • A61K36/18—Magnoliophyta (angiosperms)
  • A61K36/185—Magnoliopsida (dicotyledons)
  • A61K36/53—Lamiaceae or Labiatae (Mint family), e.g. thyme, rosemary or lavender
• • A—HUMAN NECESSITIES
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  • A61K36/18—Magnoliophyta (angiosperms)
  • A61K36/185—Magnoliopsida (dicotyledons)
  • A61K36/53—Lamiaceae or Labiatae (Mint family), e.g. thyme, rosemary or lavender
  • A61K36/534—Mentha (mint)
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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  • A61K36/18—Magnoliophyta (angiosperms)
  • A61K36/185—Magnoliopsida (dicotyledons)
  • A61K36/54—Lauraceae (Laurel family), e.g. cinnamon or sassafras
• • A—HUMAN NECESSITIES
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  • A61K36/18—Magnoliophyta (angiosperms)
  • A61K36/185—Magnoliopsida (dicotyledons)
  • A61K36/61—Myrtaceae (Myrtle family), e.g. teatree or eucalyptus
• • 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)
  • A61K36/63—Oleaceae (Olive family), e.g. jasmine, lilac or ash tree
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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  • A61K36/18—Magnoliophyta (angiosperms)
  • A61K36/185—Magnoliopsida (dicotyledons)
  • A61K36/75—Rutaceae (Rue family)
  • A61K36/752—Citrus, e.g. lime, orange or lemon
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K38/00—Medicinal preparations containing peptides
  • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
  • A61K38/43—Enzymes; Proenzymes; Derivatives thereof
  • A61K38/44—Oxidoreductases (1)
• • 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
  • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
  • A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
• • 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
  • A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
• • 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
  • A61K47/46—Ingredients of undetermined constitution or reaction products thereof, e.g. skin, bone, milk, cotton fibre, eggshell, oxgall or plant extracts
• • 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
  • A61K9/08—Solutions
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P3/00—Drugs for disorders of the metabolism
  • A61P3/02—Nutrients, e.g. vitamins, minerals
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P9/00—Drugs for disorders of the cardiovascular system
  • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
• • C—CHEMISTRY; METALLURGY
  • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
  • C12Y—ENZYMES
  • C12Y110/00—Oxidoreductases acting on diphenols and related substances as donors (1.10)
  • C12Y110/02—Oxidoreductases acting on diphenols and related substances as donors (1.10) with a cytochrome as acceptor (1.10.2)
  • C12Y110/02002—Ubiquinol-cytochrome-c reductase (1.10.2.2), i.e. electron-transport-complex-III

Definitions

• This invention relates to a stable aqueous suspension comprising a nutrient, as well as to a method of rendering a normally hydrophobic nutritional compound or ingredient dispersible in water or in an aqueous system.
• Nutritional compounds i.e. nutritional supplements, have been shown to help prevent the onset of undesirable conditions in man. These substances have been identified as either essential to human health (e.g. vitamins), or may, based on the increasing compilation of studies, play a role in maintaining health. For example, phytosterol and/or phytostanol esters have been shown to reduce serum cholesterol levels in man (mammals) upon consumption, and subsequent digestion in the gut. The mechanism for this is not completely known.
• scientists theorize that these compounds block absorption of cholesterol produced and released from the body through the normal hepatic function, or consumed as a component of food. In reducing serum cholesterol levels, current wisdom deduces that heart and circulatory health may be maintained by preventing such conditions as arteriosclerosis, myocardial infarction, etc.
• Nutritional ingredients such as lutein
• the nutritional ingredients are typically hydrophobic and are not ordinarily dispersible in aqueous systems because they are only slightly water or oil soluble, if to any degree at all.
• the nutritional ingredients are desirable for use in beverages and cosmetics, in the form of aqueous suspensions, dispersions, or liposomes. Accordingly, a means for rendering these ingredients water dispersible or dispersible in an aqueous system is needed and desired.
• This invention relates to a stable suspension comprising a nutrient or nutritional ingredient.
• the nutrient is in an ester form and is associated with a dispersion aid and a dispersion agent.
• This invention involves a stable aqueous suspension which comprises a nutrient or a nutritional compound or ingredient.
• a suitable nutrient or nutritional ingredient is one which is suitable for therapeutic treatment of an animal, e.g. a human being, by ingestion, e.g. via a beverage, or by topical application, e.g. via a lotion or cream, but which is unfortunately typically insoluble or only slightly soluble in water at room temperature, e.g. 20° C. to 25° C., i.e. it is typically hydrophobic. It is these ingredients which are the subject of this invention.
• Some suitable nutrients or nutritional ingredients include (1) a compound of the formula,
• R is OH, ⁇ -glucoside, 6′′-O-acetylglucoside, or 6′′-O-malonylglucoside;
• R′ is H or OH; and
• R′′ is H or OCH 3 ;
• isoflavone e.g. a soybean derived isoflavone, and a substituted isoflavone, such as daidzein, genistein and glycitein
• a stigmasterol sitosterol, fucosterol, brassicasterol, campesterol, clionasterol, desmosterol, chalinosterol, poriferasterol, (5) a phytostanol, e.g. ⁇ or ⁇ sitostanol, campestanol, brassicastanol, clionastanol, stigmastanol, desmostanol, chalinostanol, poriferastanol, 22, 23 dihydrobrassicastanol, etc. and (6) a mixture of any of the foregoing ingredients.
• a phytostanol e.g. ⁇ or ⁇ sitostanol, campestanol, brassicastanol, clionastanol, stigmastanol, desmostanol, chalinostanol, poriferastanol, 22, 23 dihydrobrassicastanol, etc.
• a particular nutrient or mixture of nutritional ingredients is present in the inventive aqueous dispersions or suspensions in an effective nutritional amount, that is an amount which causes its desired nutritional or therapeutic effect.
• the term “amount” as used herein refers to quantity or concentration as appropriate to the context.
• the amount of nutrient that constitutes a nutritional amount varies according to factors such as potency of the particular ingredient or mixture of ingredients, the mode of administration and the mechanical system used to administer the dispersion.
• a normally effective amount of a particular nutrient can be selected by those of ordinary skill in the art with due consideration of such factors.
• a nutritionally effective amount will be from 0.005 parts by weight to about 25 parts by weight based on 100 parts by weight of the dispersion or suspension.
• a suitable aqueous system or medium is selected.
• a suitable aqueous system or medium for the dispersions or suspensions of this invention include water and an aqueous solution of an organic alcohol of 1 to 6 carbon atoms, e.g. ethanol, propylene glycol, glycerin, etc., and a mixture of the foregoing; present in an amount of up to 10 percent (10%) by weight.
• the aqueous system is one which will permit a stable dispersion or suspension to be formed therein when combined with the selected nutrient or mixture of nutrients, which in turn is destined to be in the form of at least a mono-ester associated with a suitable dispersion aid.
• the aqueous system is present in an amount which affords the desired dispersion and is dependent upon the selected nutrient or mixture of nutritional ingredients with the selected dispersion aid. Typically, the aqueous system comprises 55 to 95 weight percent of the dispersion or suspension.
• the selected nutrient must first be converted to an ester, e.g. a mono-, di-, tri-ester, etc., if it does not already exist as at least a mono-ester.
• an ester e.g. a mono-, di-, tri-ester, etc.
• Such conversion if required, is conventionally carried out.
• a suitable dispersion aid is selected, i.e. an agent which when combined or associated with the nutrient ester modifies such ester from its crystalline form or morphous form to a dissolved form.
• the then modified nutrient compound, i.e. ester can then be further formulated or treated, e.g. pulverized, particularized, homogenized, liquefied, dispersed in oil carrier, whereby it can be easily dispersed in water or an aqueous medium as a suspension.
• a suitable dispersion aid includes (1) a triglyceride, such as sunflower oil, soy bean oil, olive oil; a medium chain triglyceride i.e. triglycerides with mixed fatty acids of C 6 to C 12 lengths, such as sn-glyceryl-1-caprylate, -2-caprate, -3-caprylate, etc., and a mixture of any of the foregoing, (2) an essential oil extractive, such as orange oil, lime oil, clove oil, oregano oil, peppermint oil, cinnamon oil, etc., and a mixture of the foregoing; (3) night primrose oil; (4) fish oils; (5) and a mixture of any of the foregoing aids.
• a triglyceride such as sunflower oil, soy bean oil, olive oil
• a medium chain triglyceride i.e. triglycerides with mixed fatty acids of C 6 to C 12 lengths, such as sn-glyceryl-1-capry
• the nutrient in ester form is combined or mixed with the dispersion aid, typically at a temperature ranging from 20 to 80° C., e.g. 70-75° C., for 2 to 10 minutes to form the nutrient ester associated with the dispersion aid.
• association means that the nutrient ester has either reacted with the dispersion aid or has physically interacted with the dispersion aid whereby it is either mixed therewith, encapsulated, wholly or partially, thereby, or becomes part of the interstices thereof, solubilized or diluted.
• a suitable dispersion agent is selected from (1) a lecithin, derived from soybean or derived from egg which contain a complex mixture of phospholipids consisting mainly of phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, and phosphatidic acid combined with varying amounts of other substances such as triglycerides: the lecithin can be of standard grade or can be modified or refined lecithin e.g. deoiled, hydrogenated, hydroxylated, enzyme modified, acetylated, etc.; (2) a hydrocolloid, e.g.
• xanthan gum starch, pectin, gelatin, guar gum, carrageenan, methylcellulose, hydroxypropyl cellulose; (3) a surfactant, e.g. cetylpyridinium chloride, polysorbate 80, sorbitan monostearate, polyglycerol esters, block copolymers of propylene oxide, ethylene oxide; (4) a mixture of any of the forgoing dispersion agents.
• a surfactant e.g. cetylpyridinium chloride, polysorbate 80, sorbitan monostearate, polyglycerol esters, block copolymers of propylene oxide, ethylene oxide
• (4) a mixture of any of the forgoing dispersion agents e.g. cetylpyridinium chloride, polysorbate 80, sorbitan monostearate, polyglycerol esters, block copolymers of propylene oxide, ethylene oxide.
• An aqueous dispersion of the selected nutrient/aid combination utilizes the dispersion agent in an amount effective to form and stabilize the resultant aqueous dispersion relative to an identical aqueous formulation not containing the dispersion agent, such that the active ingredient does not settle, cream or flocculate after agitation so quickly as to prevent reproducibility, e.g. reproducible dosing.
• Reproducible application, e.g. dosing can be achieved if the resultant aqueous suspension is substantially uniform for minimally 1 to 2 hours after agitation thereof.
• the particular amount of dispersion agent that constitutes an effective amount is dependent upon the particular dispersion agent, the particular aqueous system or medium employed and the particular nutritional ingredient/aid combination, or mixture of ingredients employed. It is therefore not practical to enumerate a specific effective amount for use with specific dispersions or formulations of the invention, but such amount can readily be determined by those of ordinary skill in the art with due consideration of the factors set forth above.
• the dispersion agent can be present in a formulation in an amount from about 0.01 percent by weight to about 20 percent by weight, more preferably about 0.05 percent to about 10 percent by weight, most preferably 0.5 percent to 5 percent by weight, based on the total weight of the dispersion or formulation.
• the dispersion aid e.g. sunflower oil
• the active ingredient or nutritional agent e.g. phytosterol esters
• the combination is added to water containing dispersion agents, and is agitated thereto to form a mixture.
• the resultant mixture is then subjected to a high shear treatment using any commercially available equipment, e.g.
• Microfluidics M110 at a shear pressure of 6500 to 24,000 psi, and preferably at a shear pressure of 7000 to 20,000 psi, and most preferably at a shear 10,000 to 12,000 psi, whereby a particle size of the active ingredient typically is less than 500 nm, preferably less than 300 nm, most preferably less than 250 nm, to form the desired aqueous dispersion or suspension.
• the resultant aqueous nutrient dispersion can then be further formulated and administered to a patient, e.g. a mammal such as a human being, by any conventional means, such as topically, orally; etc.
• a patient e.g. a mammal such as a human being
• the dispersion or suspension is combined with other drugs, adjuvants, etc. in the form of a cream or lotion, e.g. a cosmetic, or in the form of a liquid, e.g. a beverage.
• SELIN® brand phytosterol fatty acid esters from Cognis (6.0 g) was dissolved in 24.0 g of NUSUN® oil, from Archer Daniels Midland, a high oleic acid sunflower oil, at 36° C.
• the resultant solution was added to an aqueous system comprising 78.5 percent by weight of deionized water (157 g), 4.0 percent by weight BLENDMAX K® lecithin from Central Soya (8 g) and 2.5 percent polysorbate 80 (5 g).
• the resultant mixture was treated two times with a Microfluidizer® M110T from Microfluidics at 8,000 psi shear pressure to obtain a stable dispersion.
• Example 1 The procedure of Example 1 was repeated using 15 g of SELIN®, 15 g of NUSUN® oil, 157 g of deionized water, 8 g of BLENDMAX K®, and 5 g of polysorbate 80 to obtain a stable dispersion.
• SELIN® (6 g) was combined with NUSUN® oil (24 g) and heated at 60° C. for 15 minutes to form a solution.
• Deionized water (1155.8 g) and polysorbate 80 (5 g) were mixed together and heated at 60° C. for 15 minutes and then combined with the solution.
• BLENDMAX K® lecithin (8 g), citric acid (0.6 g) and potassium sorbate (0.6 g) were added to the combined solution with mixing and then the resultant mixture was passed through a M110T Microfluidizer®, two times at a shear pressure of 8,000 psi. A mean particle size of the stable dispersion of 178.3 nm was obtained.
• Example 3 The procedure of Example 3 was repeated with 10 g of SELIN®, 20 g of NUSUN® oil, 155.8 g of deionized water, 8 g of BLENDMAX K®, 5 g of polysorbate 80, 0.6 g of citric acid and 0.6 g of potassium sorbate. A mean particle size of 194.6 nm of the stable dispersion was obtained.
• Example 5 The procedure of Example 5 was repeated for lutein esters A(g) B(g) Deionized Water 72.9 67.9 BLENDMAX ® 4.0 4.0 Polysorbate 80 2.5 2.5 NUSUN ® Oil 19.8 24.75 Citric acid 0.3 0.3 Potassium sorbate 0.3 0.3 Xangold ® Lutein esters 0.2 0.25
• Example 7 The procedure of Example 7 was repeated using 3.75 g of Xangold® lutein esters and 21.25 g of olive oil instead of orange oil to obtain a stable dispersion.

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• Health & Medical Sciences (AREA)
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• 2002
  • 2002-01-03 US US10/037,573 patent/US20030129253A1/en not_active Abandoned
  • 2002-12-30 AU AU2002364054A patent/AU2002364054A1/en not_active Abandoned
  • 2002-12-30 WO PCT/US2002/041781 patent/WO2003057157A2/fr not_active Application Discontinuation
• 2003
  • 2003-10-03 US US10/678,557 patent/US20040067260A1/en not_active Abandoned
• 2007
  • 2007-11-07 US US11/936,430 patent/US20080261927A1/en not_active Abandoned
• 2012
  • 2012-04-11 US US13/444,557 patent/US20120195871A1/en not_active Abandoned
• 2013
  • 2013-03-21 US US13/848,314 patent/US20130216512A1/en not_active Abandoned
• 2014
  • 2014-07-22 US US14/338,145 patent/US9775910B2/en not_active Expired - Lifetime

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