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US5141738A Expired / Lapsed US ⏱️ 0.0 years remaining

Ultrasonic contrast medium comprising gas bubbles and solid lipophilic surfactant-containing microparticles and use thereof

Assignee: Bayer Pharma AG
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Filing: 1991-03-18
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Granted: 1992-08-25
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Expires: 2011-03-18
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Abstract

Abstract Microparticles which are less than 12 mu m in size and are formed of or comprise a solid lipophilic group-containing compound having an HLB value less than about 20 produce a long lived ultrasonically echogenic entity in aqueous liquid and are useful as left heart ultrasonic contrast image enhancing agents. Contrast media for ultrasonic diagnostics comprising a liquid vehicle containing (a) suspended therein microparticles of a mixture of at least one (C8-C20)-fatty acid and at least one solid that is not a surfactant and (b) microbubbles, are especially effective upon ultrasonic imaging after intravenous administration, for the contrasting of both the right heart and left heart, of the myocardium, as well as other organs, such as liver, spleen, and kidneys.

Inventors

  • 👤 Ned S. Rasor
  • 👤 Jurgen Hilmann
  • 👤 Lothar Lange
  • 👤 Thomas Fritzsch
  • 👤 Joachim Siegert
  • 👤 Ingfried Zimmermann

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 13:48
CPC Classifications
A; A61; A61B; A61B8/00; A61B8/48; A61B8/481; A61K; A61K49/00; A61K49/22; A61K49/222; A61K49/223; A61B90/00; A61B90/39; A61B2090/3925

Claims Analysis

Total Claims: 51
Claim 1
Independent Claim 245 words
An injectable contrast medium adapted for use as an ultrasonic diagnostic agent comprising a physiologically acceptable liquid vehicle containing suspended therein (a) microparticles comprising a mixture of (i) an amount effective to render the contrast medium suitable for use as a left heart imaging agent of at least one physiologically acceptable, essentially lipophilic surfactant selected from the group consisting of a lecithin, a lecithin fraction, a modification product of a lecithin fraction, a polyoxyethylene fatty acid ester, a polyoxyethylated sorbitan fatty acid ester, glycerol polyethylene glycol oxystearate, glycerol polyethylene glycol ricinoleate, an ethoxylated soy sterol, an ethoxylated castor oil, a hydrogenated derivative of an ethoxylated castor oil, cholesterol, a (C 8 -C 20 )-fatty acid, a physiologically acceptable salt of a (C 8 -C 20 ) fatty acid, a polyoxyethylene fatty acid, a sugar ester, a sucrose glyceride, an oxyloglyceride, a saturated (C 4 -C 20 )-fatty alcohol, an unsaturated (C 4 -C 20 ) fatty alcohol, a fatty acid, a fatty acid ester, a mono-, di-, or triglyceride, a sorbitan fatty acid, a physiologically acceptable salt of a sorbitan fatty acid, a polyoxyethylene fatty acid ester, ascorbyl palmitate, a xyloglyceride, a palm oil sucrose glyceride and a cottonseed oil sucrose glyceride, and (ii) at least one non-surfactant physiologically acceptable water soluble solid selected from the group consisting of an inorganic salt, an organic salt and a solid hydroxy compound; and (b) an amount of microbubbles effective to render the contrast medium ultrasonic image enhancing.
Claim 2
Dependent Claim 245 words
An injectable contrast medium adapted for use as an ultrasonic diagnostic agent comprising a physiologically acceptable liquid vehicle containing suspended therein (a) microparticles comprising a mixture of (i) an amount effective to render the contrast medium suitable for use as a left heart imaging agent of at least one physiologically acceptable, essentially lipophilic surfactant selected from the group consisting of a lecithin, a lecithin fraction, a modification product of a lecithin fraction, a polyoxyethylene fatty acid ester, a polyoxyethylated sorbitan fatty acid ester, glycerol polyethylene glycol oxystearate, glycerol polyethylene glycol ricinoleate, an ethoxylated soy sterol, an ethoxylated castor oil, a hydrogenated derivative of an ethoxylated castor oil, cholesterol, a (C 8 -C 20 )-fatty acid, a physiologically acceptable salt of a (C 8 -C 20 ) fatty acid, a polyoxyethylene fatty acid, a sugar ester, a sucrose glyceride, an oxyloglyceride, a saturated (C 4 -C 20 )-fatty alcohol, an unsaturated (C 4 -C 20 ) fatty alcohol, a fatty acid, a fatty acid ester, a mono-, di-, or triglyceride, a sorbitan fatty acid, a physiologically acceptable salt of a sorbitan fatty acid, a polyoxyethylene fatty acid ester, ascorbyl palmitate, a xyloglyceride, a palm oil sucrose glyceride and a cottonseed oil sucrose glyceride, and (ii) at least one non-surfactant physiologically acceptable water soluble solid selected from the group consisting of an inorganic salt, an organic salt and a solid hydroxy compound; and (b) an amount of microbubbles effective to render the contrast medium ultrasonic image enhancing.
Claim 3
Dependent Claim 16 words
A contrast medium of claim 1, wherein the microparticles comprise 0.01-5% by weight of the surfactant.
Claim 4
Dependent Claim 17 words
A contrast medium of claim 1, wherein the surfactant is a (C 8 -C 20 )-fatty acid.
Claim 5
Dependent Claim 20 words
A contrast medium of claim 3, wherein the fatty acid myristic, palmitic, stearic or arachic acid or a mixture thereof.
Claim 6
Dependent Claim 13 words
A contrast medium of claim 3, wherein the fatty acid is palmitic acid.
Claim 7
Dependent Claim 19 words
A contrast medium of claim 1, wherein the microparticles comprise 95-99.99% by weight of the non-surfactant water soluble solid.
Claim 8
Dependent Claim 15 words
A contrast medium of claim 1, wherein the non-surfactant water soluble solid is a saccharide.
Claim 9
Dependent Claim 17 words
A contrast medium of claim 7, wherein the saccharide is a galactose, fructose, glucose, lactose or alphacyclodextrin.
Claim 10
Dependent Claim 12 words
A contrast medium according to claim 7, wherein the saccharide is galactose.
Claim 11
Dependent Claim 20 words
A contrast medium according to claim 1, wherein the microparticles have a particular size of less than about 10 μm.
Claim 12
Dependent Claim 43 words
A contrast medium of claim 1, wherein the physiologically acceptable liquid vehicle is water, a physiological electrolyte solution, an aqueous solution of a mono- or polyhydric alcohol or of propylene glycol methyl ether, or an aqueous solution of a monosaccharide or a disaccharide.
Claim 13
Dependent Claim 17 words
A contrast medium of claim 1, wherein the liquid vehicle is water or an aqueous galactose solution.
Claim 14
Dependent Claim 54 words
A contrast medium of claim 1, wherein the physiologically acceptable liquid vehicle is water or an aqueous galactose solution and wherein the microparticles have a particle size of less than about 10 μm and comprise 99-99.96% wt. % of a saccharide and about 0.04-1 wt. % of a (C 8 -C 20 )-fatty acid.
Claim 15
Dependent Claim 17 words
A contrast medium of claim 13, wherein the microparticles are a mixture of palmitic acid and galactose.
Claim 16
Dependent Claim 42 words
A contrast medium of claim 1, wherein the microparticles have a size less than about 10 μm and consist essentially of about 99.9% by weight of galactose and about 0.1% by weight of palmitic acid and wherein the liquid vehicle is water.
Claim 17
Dependent Claim 253 words
Solid physiologically acceptable microbubble precursor particles adapted for use when mixed with an injectable aqueous liquid as an injectable ultrasonic diagnostic agent in the form of aggregates comprising (a) microparticles of an admixture of (i) an amount effective to render the contrast medium suitable for use as a left heart imaging agent of at least one physiologically acceptable, essentially lipophilic surfactant selected from the group consisting of a lecithin, a lecithin fraction, a modification product of a lecithin fraction, a polyoxyethylene fatty acid ester, a polyoxyethylated sorbitan fatty acid ester, glycerol polyethylene glycol oxystearate, glycerol polyethylene glycol ricinoleate, an ethoxylated soy sterol, an ethoxylated castor oil, a hydrogenated derivative of an ethoxylated castor oil, cholesterol, a (C 8 -C 20 )-fatty acid, a physiologically acceptable salt of a (C 8 -C 20 ) fatty acid, a polyoxyethylene fatty acid, a sugar ester, a sucrose glyceride, an oxyloglyceride, a saturated (C 4 -C 20 )-fatty alcohol, an unsaturated (C 4 -C 20 ) fatty alcohol, a fatty acid, a fatty acid ester, a mono-, di-, or triglyceride, a sorbitan fatty acid, a physiologically acceptable salt of a sorbitan fatty acid, a xyloglyceride, a palm oil sucrose glyceride and a cottonseed oil sucrose glyceride, and (ii) at least one non-surfactant physiologically acceptable water soluble solid selected from the group consisting of an inorganic salt, an organic salt, and a solid hydroxy compound; and (b) an amount of a gas effective to produce a suspension of microbubbles when the microbubble precursor particles are dispersed in water.
Claim 18
Dependent Claim 253 words
Solid physiologically acceptable microbubble precursor particles adapted for use when mixed with an injectable aqueous liquid as an injectable ultrasonic diagnostic agent in the form of aggregates comprising (a) microparticles of an admixture of (i) an amount effective to render the contrast medium suitable for use as a left heart imaging agent of at least one physiologically acceptable, essentially lipophilic surfactant selected from the group consisting of a lecithin, a lecithin fraction, a modification product of a lecithin fraction, a polyoxyethylene fatty acid ester, a polyoxyethylated sorbitan fatty acid ester, glycerol polyethylene glycol oxystearate, glycerol polyethylene glycol ricinoleate, an ethoxylated soy sterol, an ethoxylated castor oil, a hydrogenated derivative of an ethoxylated castor oil, cholesterol, a (C 8 -C 20 )-fatty acid, a physiologically acceptable salt of a (C 8 -C 20 ) fatty acid, a polyoxyethylene fatty acid, a sugar ester, a sucrose glyceride, an oxyloglyceride, a saturated (C 4 -C 20 )-fatty alcohol, an unsaturated (C 4 -C 20 ) fatty alcohol, a fatty acid, a fatty acid ester, a mono-, di-, or triglyceride, a sorbitan fatty acid, a physiologically acceptable salt of a sorbitan fatty acid, a xyloglyceride, a palm oil sucrose glyceride and a cottonseed oil sucrose glyceride, and (ii) at least one non-surfactant physiologically acceptable water soluble solid selected from the group consisting of an inorganic salt, an organic salt, and a solid hydroxy compound; and (b) an amount of a gas effective to produce a suspension of microbubbles when the microbubble precursor particles are dispersed in water.
Claim 19
Dependent Claim 19 words
Solid microbubble precursor particles of claim 16, wherein the microparticles have a particle size less than about 10 μm.
Claim 20
Dependent Claim 18 words
Solid microbubble precursor particles of claim 16, wherein the surfactant is a (C 8 -C 20 )-fatty acid.
Claim 21
Dependent Claim 27 words
Solid microbubble precursor particles of claim 16, wherein the microparticles consist essentially of 95-99.99% by weight of a saccharide and 5-0.01% by weight of the fatty acid.
Claim 22
Dependent Claim 17 words
Solid microbubble precursor particles of claim 19, wherein the saccharide is galactose, fructose, glucose, lactose or alpha-cyclodextrin.
Claim 23
Dependent Claim 18 words
Solid microbubble precursor particles of claim 19, wherein the fatty acid is palmitic, myristic, stearic or arachic acid.
Claim 24
Dependent Claim 20 words
Solid microbubble precursor particles of claim 19, wherein the fatty acid is palmitic acid and wherein the saccharide is galactose.
Claim 25
Dependent Claim 36 words
Solid microbubble precursor particles of claim 19, wherein the microparticles have a size less than about 10 μm and consist essentially of about 99.9% by weight of galactose and about 0.1% by weight of palmitic acid.
Claim 26
Dependent Claim 59 words
A kit adapted for the preparation of an injectable ultrasound contrast medium, which kit comprises a first container containing solid microbubble precursor particles of claim 16, and a second container containing a physiologically acceptable injectable liquid vehicle for the precursor particles which, when mixed therewith, forms an injectable contrast medium suitable for use as a left heart imaging agent.
Claim 27
Dependent Claim 16 words
A kit according to claim 24, wherein the microparticles comprise 0.01--5% by weight of the surfactant.
Claim 28
Dependent Claim 17 words
A kit according to claim 4, wherein the surfactant is a (C 8 -C 20 )-fatty acid.
Claim 29
Dependent Claim 21 words
A kit according to claim 26, wherein the fatty acid is myristic, palmitic, stearic or arachic acid or a mixture thereof.
Claim 30
Dependent Claim 13 words
A kit according to claim 26, wherein the fatty acid is palmitic acid.
Claim 31
Dependent Claim 19 words
A kit according to claim 24, wherein the microparticles comprise 95-99.99% by weight of the non-surfactant water soluble solid.
Claim 32
Dependent Claim 15 words
A kit according to claim 24, wherein the non-surfactant water soluble solid is a saccharide.
Claim 33
Dependent Claim 16 words
A kit according to claim 30, wherein the saccharide is galactose, fructose, glucose, lactose, or alphacyclodextrin.
Claim 34
Dependent Claim 11 words
A kit according to claim 31, wherein the saccharide is galactose.
Claim 35
Dependent Claim 19 words
A kit according to claim 24, wherein the microparticles have a particular size of less than about 10 μm.
Claim 36
Dependent Claim 40 words
A kit according to claim 24, wherein the physiologically acceptable liquid vehicle is water, a physiological electrolyte solution, or an aqueous solution of a mono- or polyhydric alcohol, of propylene glycol methyl ether, or of a monosaccharide or a disaccharide.
Claim 37
Dependent Claim 17 words
A kit according to claim 24, wherein the liquid vehicle is water or an aqueous galactose solution.
Claim 38
Dependent Claim 54 words
A kit according to claim 24, wherein the physiologically acceptable liquid vehicle is water or an aqueous galactose solution and wherein the microparticles have a particle size of less than about 10 μm and comprise 99-99.96% wt. % of a saccharide and about 0.04-1 wt. % of a (C 8 -C 20 )-fatty acid.
Claim 39
Dependent Claim 17 words
A kit according to claim 36, wherein the microparticles are a mixture of palmitic acid and galactose.
Claim 40
Dependent Claim 41 words
A kit according to claim 24, wherein the microparticles have a size less than about 10 μm and consist essentially of about 99.9% by weight of galactose and about 0.1% by weight of palmitic acid and the liquid vehicle is water.
Claim 41
Independent Claim 374 words
A method for altering the transmission characteristics of an aqueous liquid to an electromagnetic or elastic wave transmitted therethrough by dispersing in the liquid an amount effective to alter said transmission characteristics of a solid microbubble precursor particles which contains an amount of a gas effective to produce a suspension of microbubbles which alters the transmission characteristics of the liquid when the precursor is dispersed in the liquid and which, when dispersed in the liquid, forms an ultrasonically ectogenic entity including a gas phase which alters those transmission characteristics, which comprises employing a microbubble precursor containing a solid phase consisting essentially of an intimate mixture of 95-99.99% by weight of (a) at least one water soluble solid selected from the group consisting of an inorganic salt, an organic salt and a solid hydroxy compound, and (b) an amount from 5-0.01% by weight of a solid lipophilic group-containing compound effective to prevent the dissolution of the water soluble solid for at least about three seconds after the precursor is dispersed in the liquid, which lipophilic group-containing compound has an HLB (Hydrophilic-Lipophilic Balance) value, in the form that compound exists in the liquid, of no greater than about 20 and is selected from the group consisting of a lecithin, a lecithin fraction, a modification product of a lecithin fraction, a polyoxyethylene fatty acid ester, a polyoxyethylated sorbitan fatty acid ester, glycerol polyethylene glycol oxystearate, glycerol polyethylene glycol ricinoleate, an ethoxylated soy sterol, an ethoxylated castor oil, a hydrogenated derivative of an ethoxylated castor oil, cholesterol, a (C 8 -C 20 )-fatty acid, a physiologically acceptable salt of a (C 8 -C 20 ) fatty acid, a polyoxyethylene fatty acid, a sugar ester, a sucrose glyceride, an oxyloglyceride, a saturated (C 4 -C 20 )-fatty alcohol, an unsaturated (C 4 -C 20 ) fatty alcohol, a fatty acid, a fatty acid ester, a mono-, di-, or triglyceride, a sorbitan fatty acid, a physiologically acceptable salt of a sorbitan fatty acid, a polyoxyethylene fatty acid ester, ascorbyl palmitate, a xyloglyceride, a palm oil sucrose glyceride and a cottonseed oil sucrose glyceride, which microbubble precursor also comprises (c) an amount of a gas effective to produce a suspension of microbubbles when the solid phase is dispersed in the liquid.
Claim 42
Independent Claim 374 words
A method for altering the transmission characteristics of an aqueous liquid to an electromagnetic or elastic wave transmitted therethrough by dispersing in the liquid an amount effective to alter said transmission characteristics of a solid microbubble precursor particles which contains an amount of a gas effective to produce a suspension of microbubbles which alters the transmission characteristics of the liquid when the precursor is dispersed in the liquid and which, when dispersed in the liquid, forms an ultrasonically ectogenic entity including a gas phase which alters those transmission characteristics, which comprises employing a microbubble precursor containing a solid phase consisting essentially of an intimate mixture of 95-99.99% by weight of (a) at least one water soluble solid selected from the group consisting of an inorganic salt, an organic salt and a solid hydroxy compound, and (b) an amount from 5-0.01% by weight of a solid lipophilic group-containing compound effective to prevent the dissolution of the water soluble solid for at least about three seconds after the precursor is dispersed in the liquid, which lipophilic group-containing compound has an HLB (Hydrophilic-Lipophilic Balance) value, in the form that compound exists in the liquid, of no greater than about 20 and is selected from the group consisting of a lecithin, a lecithin fraction, a modification product of a lecithin fraction, a polyoxyethylene fatty acid ester, a polyoxyethylated sorbitan fatty acid ester, glycerol polyethylene glycol oxystearate, glycerol polyethylene glycol ricinoleate, an ethoxylated soy sterol, an ethoxylated castor oil, a hydrogenated derivative of an ethoxylated castor oil, cholesterol, a (C 8 -C 20 )-fatty acid, a physiologically acceptable salt of a (C 8 -C 20 ) fatty acid, a polyoxyethylene fatty acid, a sugar ester, a sucrose glyceride, an oxyloglyceride, a saturated (C 4 -C 20 )-fatty alcohol, an unsaturated (C 4 -C 20 ) fatty alcohol, a fatty acid, a fatty acid ester, a mono-, di-, or triglyceride, a sorbitan fatty acid, a physiologically acceptable salt of a sorbitan fatty acid, a polyoxyethylene fatty acid ester, ascorbyl palmitate, a xyloglyceride, a palm oil sucrose glyceride and a cottonseed oil sucrose glyceride, which microbubble precursor also comprises (c) an amount of a gas effective to produce a suspension of microbubbles when the solid phase is dispersed in the liquid.
Claim 43
Dependent Claim 50 words
The method according to claim 39, wherein the aqueous liquid is the blood stream of a living being, the particulate solid is non-toxic and physiologically acceptable in the amount dispersed therein and is injected into the blood stream as a suspension in a non-toxic physiologically acceptable intravenously injectable liquid vehicle.
Claim 44
Dependent Claim 17 words
The method according to claim 39, wherein the surfactant is a (C 8 -C 20 )-fatty acid.
Claim 45
Dependent Claim 21 words
The method according to claim 41, wherein the fatty acid is myristic, palmitic, stearic or arachic acid or a mixture thereof.
Claim 46
Dependent Claim 13 words
The method according to claim 41, wherein the fatty acid is palmitic acid.
Claim 47
Dependent Claim 15 words
The method according to claim 39, wherein the non-surfactant water soluble solid is a saccharide.
Claim 48
Dependent Claim 16 words
The method according to claim 44, wherein the saccharide is galactose, fructose, glucose, lactose or alphacyclodextrin.
Claim 49
Dependent Claim 11 words
The method according to claim 44, wherein the saccharide is galactose.
Claim 50
Dependent Claim 54 words
The method according to claim 41, wherein the physiologically acceptable liquid vehicle is water or an aqueous galactose solution and wherein the microparticles have a particle size of less than about 10 μm and comprise 99-99.96% wt. % of a saccharide and about 0.04-1 wt. % of a (C 8 -C 20 )-fatty acid.
Claim 51
Dependent Claim 17 words
The method according to claim 47, wherein the microparticles are a mixture of palmitic acid and galactose.

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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
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