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WO2025043046A1 - Compositions à base d'huile compatibles avec le latex - Google Patents

Compositions à base d'huile compatibles avec le latex Download PDF

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Publication number
WO2025043046A1
WO2025043046A1 PCT/US2024/043335 US2024043335W WO2025043046A1 WO 2025043046 A1 WO2025043046 A1 WO 2025043046A1 US 2024043335 W US2024043335 W US 2024043335W WO 2025043046 A1 WO2025043046 A1 WO 2025043046A1
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Prior art keywords
oil
composition
oil component
weight
amount
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English (en)
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David Michael STEVENS
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Glycosbio Inc
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Glycosbio Inc
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents

Definitions

  • W02019075307A1 and W02020150661A1 are directed to methods of making enzyme- modified oils (EMOs) and EMO compositions and the contents of each are incorporated by reference herein in their entirety.
  • WO2022221470A1 is directed to drug delivery EMO compositions and methods of making the same, the contents of which are incorporated by reference herein in its entirety.
  • WO2022221472A1 is directed to EMO compositions and EMO-based products with antimicrobial properties and methods of making the same, the contents of which are incorporated by reference herein in its entirety.
  • Mineral oil and plant-based oils are generally understood to be incompatible with latex -based materials, such as those used in gloves or condoms.
  • water-based materials and silicone oil are recommended for use with latex -based materials, but these are generally synthetic materials and may not be ideal for topical applications (e.g., lubricants or drug compositions).
  • a natural oil substance that avoids the deleterious effects on latex -based materials is needed.
  • the present disclosure is related to oil-derived substances that can be used in latex rubber applications such as lubricants and coatings for condoms. These oil-derived substances also demonstrate enhanced drug delivery and antimicrobial properties that are useful in latex rubber products. The present disclosure is therefore directed to enhanced latex rubber products and oil-based lubricants and coatings for use with latex rubber products.
  • a device comprising an elastic material and a first composition
  • the first composition comprises an oil component, wherein the oil component comprises monoacyl glycerols (MAGs), diacylglycerols (DAGs) or a combination of MAGs and DAGs, wherein the oil component is either substantially free of triacylglycerols (TAGs) or comprises less than 5% TAGs; and wherein the first composition is in contact with the elastic material.
  • MAGs monoacyl glycerols
  • DAGs diacylglycerols
  • TAGs triacylglycerols
  • a composition comprising a first oil component in an emulsion such that the first oil component is dispersed in a liquid, and wherein the first oil component is in the form of droplets or particles, wherein the first oil component comprises from about 1% to about 30% by weight of the total weight of the composition, wherein the first oil component comprises monoacyl glycerols (MAGs) in an amount from 40% to about 100% by weight based on the total weigh of the first oil component, wherein the first oil component is either substantially free of triacylglycerols (TAGs) or comprises TAGs in an amount of less than 5% by weight based on the total weight of the first oil component, wherein the first oil component is either substantially free of free fatty acids or comprises free fatty acids in an amount that is less than 20% by weight of the total weight of the first oil component, wherein the first oil component is either substantially free of diacylglycerols (DAGs) or comprises DAGs in an amount of less than 50%
  • emulsion refers to a colloidal particulate system consisting of two immiscible liquids, or a liquid and a solid, in which one liquid or the solid (dispersed phase) is dispersed as a droplet or particle, respective into the other liquid (continuous phase).
  • a “microemulsion” is an emulsion that can include droplets or particles have a size greater than 1000 nm to 1000000 nm.
  • a “nanoemulsion” is an emulsion that can include droplets or particles having a size from 10 to 1000 nm, but generally nanoemulsions must have small droplet sizes ( ⁇ 300 nm) in order to be kinetically stable.
  • the dispersed phase is also known as the discontinuous phase while the outer phase can be called the continuous phase.
  • elastic material means material that has the ability to stretch or expand upon the application of force and following removal of the force, resume its original shape and/or size. It should be understood that in some cases, the amount or duration of force could be great enough that the material does not entirely resume its precise original size or shape, but that a material will still be considered “elastic” if the size or shape is greater when force is applied and less in the absence of such force.
  • Non-limiting examples of elastic material as the term is intended herein include rubber, latex rubber, nitrile rubber, polyurethane, polyisoprene or animal intestine.
  • free fatty acid refers to a non-esterified fatty acid in its carboxylic acid form or carboxylate salt form.
  • MAG monoacylglycerol
  • DAG diacylglycerol
  • a “triacylglycerol (TAG),” also known as a triglyceride, is a glyceride consisting of three fatty acid chains covalently bonded to a glycerol molecule through ester linkages. TAGs may also be classified as having a long or medium chain length. Long chain TAGs contain fatty acids with 14 or more carbons, while medium chain TAGs contain fatty acids with 6 to 12 carbons. Long chain TAGs can include omega-3 and omega-6 fatty acids. Medium chain TAGs have saturated fatty acids and thus do not contain omega-3 or omega-6 fatty acids. Long chain TAGs (LCT) and medium chain triglycerides (MCT) can serve as energy sources.
  • TAGs long chain TAGs
  • MCT medium chain triglycerides
  • EMO enzyme-modified oil
  • an EMO refers to an oil that includes MAGs and, optionally DAGs and/or FFA that results from enzymatic hydrolysis of a starting oil source(s) to yield FFA and glycerol followed by separation of the glycerol, and at least partial enzymatic reesterification of glycerol with the FFA to yield MAGs and, optionally some DAGs, and, in some instances, some FFAs.
  • an EMO should be understood to be substantially free of TAGs (below a detectable level). In some embodiments, an EMO can have less than 5% TAGs.
  • a “therapeutically effective amount” refers to an amount of a composition of the present disclosure effective yield a desired therapeutic response.
  • an amount effective to reduce sensation, pain or inflammation can be “therapeutically effective amount.”
  • the specific therapeutically effective amount will vary with such factors as the particular condition being treated, the physical condition of the subject, the type of subject being treated, the duration of the treatment, the nature of concurrent therapy (if any), and the specific formulations employed and the structure of the composition.
  • an “active ingredient” is a substance that is intended for use in the diagnosis, cure, mitigation, treatment or prevention of disease, or to affect the structure or function of the body of a subject, such as a mammal, preferably a human.
  • an active ingredient can be a pharmaceutically active substance, including, but not limited to, a steroid, peptide, protein, synthetic chemical molecule, a plant extract, vitamin, nucleic acid and antioxidant.
  • a “subject” refers to any living being, such as a human being or animal. Oil Compositions
  • an oil composition which includes monoacyl glycerols (MAGs), diacylglycerols (DAGs) or combinations thereof and where the oil composition is substantially free of triacylglycerols (TAGs).
  • the oil compositions of the present disclosure may include free fatty acids (FFAs).
  • the oil composition can include from about 1% to about 99%, about 10% to about 90%, about 40% to about 90%, about 15% to about 80%, about 20% to about 80%, about 25% to about 80%, about 30% to about 80%, about 40% to about 80%, about 50% to about 80%, about 60% to about 80%, about 70% to about 80%, about 75% to about 80%, about 10% to about 75%, about 15% to about 75%, about 20% to about 75%, about 25% to about 75%, about 30% to about 75%, about 40% to about 75%, about 50% to about 75%, about 60% to about 75%, about 70% to about 75%, about 10% to about 70%, about 15% to about 70%, about 20% to about 70% about 25% to about 70%, about 30% to about 70%, about 40% to about 70%, about 50% to about 70%, about 60% to about 70%, about 10% to about 60%, about 15% to about 60%, about 20% to about 60%, about 25% to about 60%, about 30% to about 60%, about 40% to about 60%, about 50% to about 60%, about 70%, about 10% to about 60%, about 15% to
  • the combined amount of the MAGs and DAGs can be from about 50% to about 99%, about 60% to about 99%, about 70% to about 99%, about 80% to about 99%, about 60% to about 95%, about 70% to about 95%, about 75% to about 95%, about 80% to about 95%, about 90% to about 95%, about 60% to about 90%, about 70% to about 90%, about 75% to about 90%, about 80% to about 90%, about 60% to about 80%, about 70% to about 80%, about 75% to about 80%, about 60% to about 75%, about 70% to about 75%, about 60% to about 70%, or 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, or 99% by weight out of the total weight of the oil.
  • the oil can have a fatty acid profile comprising two, three, four, five, six, seven, eight, nine, ten, eleven, or twelve of C6:0, C8:0, CIO, Cl 2, Cl 4, Cl 6, C18, C18: l, C18:2, C18:3, C20 and C22, wherein a range of each fatty is acid is between about 0.1% and 85% out of the total fatty acid content.
  • the amount can be from about 0.1% to about 85%, about 0.5% to about 85%, about 1% to about 85%, about 2% to about 85%, about 3% to about 85%, about 4% to about 85%, about 5% to about 85%, about 10% to about 85%, about 15% to about 85%, about 20% to about 85%, about 25% to about 85%, about 30% to about 85%, about 35% to about 85%, about 40% to about 85%, about 45% to about 85%, about 50% to about 85%, about 55% to about 85%, about 60% to about 85%, about 65% to about 85%, about 70% to about 85%, about 75% to about 85%, about 80% to about 85%, about 0.1% to about 80%, about 0.5% to about 80%, about 1% to about 80%, about 2% to about 80%, about 3% to about 80%, about 4% to about 80%, about 5% to about 80%, about 10% to about 80%, about 15% to about 85%, about 20% to about 85%, about 25% to about
  • the oil, or a portion thereof such as, by way of example, but not limitation, an EMO, can be an oil source selected from a plant, an animal, a fish, an algal oil, and combinations thereof.
  • the oil of the compositions of the present disclosure can include two, three, four or more oils from various source oils.
  • the oils source for the oil composition of the foregoing embodiments are selected from flaxseed oil, rosehip oil, olive oil, canola oil, sesame oil, hemp seed oil, sunflower oil, almond oil, coconut oil, oat oil, and any combination thereof.
  • the oil is not a fish oil, anchovy oil, algal oil, chicken fat, lard, or krill oil.
  • the two or more different fatty acids can comprise two or more fatty acids from C8:0 in an amount from about 50% to about 65% out of the total fatty acid content of the oil and CIO in an amount from about 35% to about 50% out of the total fatty acid content of the oil.
  • the two or more different fatty acids can comprise two or more fatty acids from Cl 8: 1 in an amount from about 15% to about 25% out of the total fatty acid content of the oil, C18:2 in an amount from about 45% to about 55% out of the total fatty acid content of the oil, and Cl 8:3 in an amount from about 15% to about 25% out of the total fatty acid content of the oil.
  • the two or more different fatty acids can comprise two or more fatty acids from C18 in an amount from about 10% to about 20% out of the total fatty acid content, Cl 8: 1 in an amount from about 35% to about 45% out of the total fatty acid content, C18:2 in an amount from about 30% to about 45% out of the total fatty acid content of the oil.
  • the two or more different fatty acids can comprise two or more fatty acids from Cl 8: 1 in an amount from about 5% to about 20% out of the total fatty acid content, Cl 8:2 in an amount from about 50% to about 65% out of the total fatty acid content, Cl 8:3 in an amount from about 15% to about 25% out of the total fatty acid content of the oil.
  • the two or more different fatty acids can comprise two or more fatty acids from Cl 8: 1 in an amount from about 15% to about 25% out of the total fatty acid content and Cl 8:2 in an amount from about 60% to about 80% out of the total fatty acid content of the oil.
  • the two or more different fatty acids can comprise two or more fatty acids from C18: l in an amount from about 55% to about 70% out of the total fatty acid content and C18:2 in an amount from about 15% to about 30% out of the total fatty acid content of the oil.
  • the two or more different fatty acids can comprise two or more fatty acids Cl 8: 1 in an amount from about 60% to about 80% out of the total fatty acid content and Cl 8:2 in an amount from about 10% to about 25% out of the total fatty acid content of the oil.
  • the two or more different fatty acids can comprise two or more fatty acids from C 16 in an amount from about 5% to about 20% out of the total fatty acid content, C18: 1 in an amount from about 15% to about 30% out of the total fatty acid content, and Cl 8:2 in an amount from about 45% to about 60% out of the total fatty acid content of the oil.
  • the oil composition can have a tri acyl glycerol (TAG) content of 20% or less TAGs by weight based on the total weight of the oil composition.
  • TAG content can be equal to or less than 20%, can be equal to or less than 15%, can be equal to or less than 10%, can be equal to or less than 5%, can be equal to or less than 4%, equal to or less than 3%, equal to or less than 2%, equal to or less than 1% by weight based on the total weight of the oil composition or the oil composition can be substantially free of TAGs.
  • the oil may have the MAG, DAG and FFA content as disclosed above regardless of the oil used.
  • the non-oil ingredients derived from and naturally present in the oil source can include ceramide phosphate, monoglactodiacylglycerol, phosphatidylmethanol, sitosteryl ester, campesterol ester, sphingolipids, phosphatidyl glycerol, wax esters, sphingomyelin, or combinations thereof.
  • the non-oil ingredients derived from and naturally present in the oil source can include a-tocopherol, B-tocopherol, 5- tocopherol, y-tocopherol, a-tocotrienol, B-tocotrienol, 5-tocotrienol, y-tocotrienol, or combinations thereof.
  • the non-oil ingredients derived from and naturally present in the oil source are present in the EMO in an amount or relative amount characteristic of or increased relative to the amounts or relative amounts, respectively, in the oil source. It should be understood that the level of the non-oil ingredients can generally be the same as or greater than that in the oil source.
  • the non-oil components can be determined by LC/MS/MS analysis.
  • the MAGs in the EMO (or oil composition) can have a sn-1 substitution to sn-2 substitution ratio of greater than 1.
  • the MAGs in the EMO (or oil composition) can have a sn-1 substitution to sn-2 substitution ratio of greater than 1, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2, 2.25, 2.5, 2.75, 3, 3.25, 3.5, 3.75, 4, 4.25, 4.5, 4.75, 5, 6, 7, 8, 9, 10, 15, 20, 25, 30, 40, 50 or 100.
  • sn- l/sn-2 ratio can be determined by TLC or HPLC.
  • the EMO can include free fatty acids (FFA).
  • FFA free fatty acids
  • the EMO can include a FFA content equal to or less than 20% by weight of the total weight of the EMO.
  • the EMO can include a FFA content of about 1% to about 20%, about 5% to about 20%, about 10% to about 20%, about 1% to about 10%, about 5% to about 10%, about 15% to about 20%, or about 1%, 2%, 3%, 4%, 5%, 10%, 15%, or 20% by weight of the total weight of the EMO.
  • the EMO can have fatty acid profile comprising an amount of two or more fatty acids, wherein the amount of each of the two or more fatty acids within 10% of the amount of each of the two or more fatty acids in the first oil source.
  • the EMO can have between about 5-25%, 6-24%, 7-23%, 8-22%, 9-21%, 10-20%, 11- 19%, 12-18%, 13-17%, 14-16% or about 15% Cl 8 fatty acid.
  • the EMO (or other oil composition) can be substantially free of 3 -monochloropropanediol and glycidol equivalents.
  • the oil composition can be in the form of an emulsion wherein any of the above oil compositions are dispersed in a liquid, where the oil is in the form of droplets or particles.
  • WO2022221470A1 which is incorporated herein by reference, provides methods for manufacturing emulsions that may be useful in the embodiments of the present disclosure for enhanced stability and delivery of active ingredients.
  • compositions of the present disclosure can also be formulated as emulsions.
  • the droplets or particles can have a Z average size of greater than about 300 nm or greater than about 1000 nm.
  • the particle size can be measured by microscopy or dynamic light scattering.
  • Methods of making emulsions are well-known in the art and include, by way of example, but not limitation, homogenization, sonication, solvent evaporation, supercritical fluid methods, spray drying methods and double emulsion methods.
  • the oil compositions of the foregoing embodiments may be used as the primary carriers for active ingredients (e.g., from about 50% to about 100% EMO) or may be used as additives for other compositions used in latex-based articles and compositions.
  • the oil compositions (including EMOs) may be present in the primary compositions in an amount from about 1% to about 50% by weight of the total weight of the primary composition, from about 1% to about 40% by weight of the total weight of the primary composition, from about 1% to about 40% by weight of the total weight of the primary composition, from about 1% to about 30% by weight of the total weight of the primary composition, from about 1% to about 20% by weight of the total weight of the primary composition, from about 1% to about 10% by weight of the total weight of the primary composition, from about 2% to about 20% by weight of the total weight of the primary composition, from about 5% to about 20% by weight of the total weight of the primary composition, from about 3% to about 10% by weight of the total weight of the primary composition, from about 2%
  • the active ingredient can be an antibiotic, anti-viral drug, anti-parasitic drug, antifungal drug, anti-cancer drug, steroid drug, nonsteroidal drug, narcotic analgesic drug, local analgesic drug, immunosuppressant drug, or a vitamin or nutritional supplement.
  • antibiotics include: clarithromycin A, bacitracin, neomycin, polymyxin B, mupirocin, or cyclosporine.
  • anti-viral drugs include: acyclovir, famciclovir, valacyclovir, famciclovir, penciclovir, cidofovir, or foscarnet.
  • Non-limiting examples of steroid drugs include: hydrocortisone, prednisone, prednisolone, clobetasol propionate, triamcinolone, triamcinolone acetonide, testosterone, prasterone, or estradiol.
  • Non-limiting examples of nonsteroidal drugs include: ibuprofen, crisaborole, diclofenac, aceclofenac, celecoxib, ketoprofen, meloxicam, piroxicam, benvitimod, aspirin, salicylic acid, or naproxen.
  • Non-limiting examples of narcotic analgesic drugs include: fentanyl, sufentanil, morphine, codeine, hydromorphone, hydrocodone, oxycodone, oxymorphone, or tramadol.
  • Non-limiting examples of local analgesic drugs include procaine, butacaine, benzocaine, lidocaine, bupivacaine, prilocaine, tetracaine, carbocaine, chloroprocaine, etidocaine, articaine, dibucaine, piperocaine, and combinations thereof.
  • vitamins or nutritional supplements include: vitamin A, B vitamins, vitamin C, vitamin D, vitamin E, vitamin K, curcumin, cannabidiol (CBD), cannabinoids, tetrahydrocannabinol (THC), avenanthramides, epigallocatechin gallate (EGCG), berberine, inulin, glycyrrhizin, caffeine, capsaicin, or resveratrol.
  • the active ingredient can be a drug suitable to treat or prevent acne, pain, inflammation, cancer or a vitamin or anti-aging compound.
  • the active ingredient can be aspartyl-alanyl- diketopiperazine (DA-DKP), retinol, retinyl palmitate, trifuoroacetyl tripeptide-2, or hexapeptide- 11.
  • D-DKP aspartyl-alanyl- diketopiperazine
  • retinol retinyl palmitate
  • trifuoroacetyl tripeptide-2 or hexapeptide- 11.
  • the active ingredient is fat-soluble.
  • the active ingredient is hydrophobic.
  • the active ingredient can have a logP (octanolwater partition coefficient) value of about 1 to about 6.
  • the active ingredient can have a logP value of about 1 to about 6, about 1 to about 5, about 1 to about 4, about 1 to about 3, about 1 to about 2, about 2 to about 6, about 2 to about 5, about 2 to about 4, about 2 to about 3, about 3 to about 6, about 3 to about 5, about 3 to about 4, about 4 to about 6, about 4 to about 5, about 1, 1.5, 2, 2.5, 3, 3.5, 4, 4.5, 5, 5.5 or 6.
  • the active ingredient can be cannabidiol (CBD), vitamin E or carotene. It should be understood, however, that the active ingredient, in certain aspects, can be hydrophilic. By way of example, but limitation, for transdermal applications, the active ingredient can be hydrophilic.
  • the hydrophilic active ingredient can have a logP of less than 1, such as from about -3 to about 1, about -2 to about 1, about -1 to about 1, about 0 to about 1, about -3, -2.5, -2, -1.5, -1, -0.5, 0, 0.5 or 1. It should be understood that the logP can be as measured or predicted.
  • the active ingredient is hydrophilic, it should be understood that it can be present in an aqueous phase of the emulsion of the present disclosure.
  • such a composition can be used for transdermal delivery of the active ingredient.
  • the active ingredient can be present in the active composition at a concentration of about 0.001 mg/mL to about 10 mg/mL or more.
  • the active ingredient can be present in the active composition at a concentration of about 0.001 to about 10 mg/mL, about 0.01 to about 10 mg/mL, about 0.1 to about 10 mg/mL, about 0.5 to about 10 mg/mL, about 1 to about 10 mg/mL, about 2.5 to about 10 mg/mL, about 5 to about 10 mg/mL, about 7.5 to about 10 mg/mL, about 0.001 to about 5 mg/mL, about 0.01 to about 5 mg/mL, about 0.1 to about 5 mg/mL, about 0.5 to about 5 mg/mL, about 1 to about 5 mg/mL, about 2 to about 5 mg/mL, about 3 to about 5 mg/mL, about 4 to about 5 mg/mL, about 1, 1.5, 2, 2.5, 3, 3.5, 4,
  • the active ingredient can be present in the active composition at higher than 10 mg/mL, such as about 10, 12.5, 15, 17.5, 20, 25 mg/mL or more.
  • the active ingredient can be present in the active composition in a therapeutically relevant concentration.
  • a therapeutically relevant concentration can be understood as a concentration sufficient to have a desired therapeutic effect.
  • the desired therapeutic effect can be to diagnose, cure, mitigate, treat or prevent disease or to affect the structure or function of the body of a subject a change in the structure or function of the body of a subject.
  • the active ingredient can have a skin permeability of at least 0.1 pg/cm2 for the active ingredient over a period of 4, 5, 6, 7, 8 or 24 hours.
  • the skin permeability can be as measured by HPLC across artificial skin, such as a Strat-M membrane.
  • the active ingredient in the oil compositions can have a skin permeability of at least 0.1 pg/cm2, at least 0.2 pg/cm2, at least 0.3 pg/cm2, at least 0.4 pg/cm2, at least 0.5 pg/cm2, at least 0.75 pg/cm2, at least 1.0 pg/cm2, at least 1.5 pg/cm2, at least 2.0 pg/cm2, at least 2.5 pg/cm2, at least 3.0 pg/cm2, at least 3.5 pg/cm2, at least 4.0 pg/cm2, at least 4.5 pg/cm2, at least 5.0 pg/cm2, at least 6 pg/cm2, at least 7 pg/cm2, at least 8 pg/cm2, at least 9 pg/cm2, at least 10 pg/cm2, at least
  • the active ingredient can be present in the primary (first) composition (with the oil composition as an additive therein or with the oil composition as the primary composition) in an amount from about 1% to about 20% by weight of the total weight of the primary composition, from about 1% to about 15% by weight of the total weight of the primary composition, from about 1% to about 10% by weight of the total weight of the primary composition, from about 1% to about 5% by weight of the total weight of the primary composition, from about 0.1% to about 10% by weight of the total weight of the primary composition, from about 0.1% to about 5% by weight of the total weight of the primary composition, or preferably form about 2% to about 8% by weight of the total weight of the composition.
  • the foregoing embodiments relate to compositions that are compatible with elastic materials that are generally known to not be compatible with certain types of oils, namely plant or vegetablebased oils.
  • These elastic materials include rubber, latex rubber, nitrile rubber, polyurethane, polyisoprene or animal intestine and articles or devices made from the same.
  • the device comprises a hollow, tubular member of an elastic material having an open end, a closed end, an internal surface and an external surface, wherein the oil compositions can be applied to the internal surface only, to the external surface only, or to both in internal and external surfaces.
  • the devices are condoms or gloves.
  • the primary (first) compositions or oil compositions may be lubricants or pastes applied to devices or articles.
  • the primary compositions and/oil compositions may be provided as separate products (e.g. lubricants) that are suitable for use with such devices and articles.
  • the oil compositions of the present disclosure are used as additives or as the primary composition for a lubricant for use in sexual activity or for medical procedures.
  • the oil compositions of the present disclosure are applied to the internal or external surfaces of condoms as a lubricant (with or without active ingredients) or as numbing paste for the internal surface of a condom (the surface that is in direct contact with the penis).
  • the oil components of the present disclosure are formulated in a composition as emulsions, the composition may possess an osmolality of less than 1,200 mOsmol/kg.
  • the oil component itself prior to formulation as an emulsion and therefore dilution in the liquid
  • the oil compositions of the present disclosure are particularly suitable for use in condoms or medical procedures given their antimicrobial properties and their ability to enhance skin penetration of active ingredients as demonstrated in WO2022221472A1 and WO2022221470A1, respectively.
  • the condoms may generally include all sizes and types that are generally available.
  • Non-limiting examples of condom dimensions include a length from about 100 mm to about 300 mm, a flat width from about 40 mm to about 70 mm, and a thickness from about 30 pm to about 100 pm.
  • the oil compositions of the present disclosure may be formulated with additional ingredients such as silicone, butylene glycol, propylene glycol, glycerin (glycerol), dimethicone, cyclomethicone, cyclopentasiolxane, polyehtylene glycol, propanediol, polyoxyethylene, and carboxymethylcellulose, hydroxyethylcellulose.
  • additional ingredients such as silicone, butylene glycol, propylene glycol, glycerin (glycerol), dimethicone, cyclomethicone, cyclopentasiolxane, polyehtylene glycol, propanediol, polyoxyethylene, and carboxymethylcellulose, hydroxyethylcellulose.
  • Embodiment 1 A device comprising an elastic material component and a first composition comprising an oil component, wherein the oil component comprises monoacylglycerols (MAGs), diacylglycerols (DAGs) or a combination of MAGs and DAGs, wherein the oil component is either substantially free of triacylglycerols (TAGs) or comprises less than 5% TAGs; and wherein the first composition is in contact with a surface of the elastic material component.
  • MAGs monoacylglycerols
  • DAGs diacylglycerols
  • TAGs triacylglycerols
  • the elastic material is selected from the group consisting of rubber, latex rubber, polyurethane, polyisoprene, nitrile rubber, or animal intestine.
  • the oil component is derived from a source oil selected from the group consisting of flaxseed oil, rosehip oil, olive oil, canola oil, sesame oil, hemp seed oil, sunflower oil, almond oil, coconut oil, oat oil, fractionated coconut oil, and any combination thereof.
  • the stabilizer is selected from the group consisting of xanthan gum, gum arabic, guar gum, agar, carrageenan, locust bean gum, carboxymethylcellulose, gelatin, pectin, and starch, or any combination thereof.
  • the local anesthetic agent is selected from the group consisting of procaine, butacaine, benzocaine, lidocaine, bupivacaine, prilocaine, tetracaine, carbocaine, chloroprocaine, etidocaine, articaine, dibucaine, piperocaine, and combinations thereof.
  • the second composition is a lubricant.
  • the elastic material component is a hollow, tubular member of an elastic material having an open end, a closed end, an internal surface and an external surface, and wherein the first composition is in contact with either or both of the internal and external surface.
  • the hollow, tubular member has a length from about 100 mm to about 300 mm, a flat width from about 40 mm to about 70 mm, and a thickness from about 30 pm to about 100 pm.
  • Embodiment 2 A composition comprising an oil component, wherein the oil component comprises monoacyl glycerols (MAGs), diacylglycerols (DAGs) or a combination of MAGs and DAGs, wherein the oil component is either substantially free of triacylglycerols (TAGs) or comprises TAGs in an amount of less than 5% by weight based on the total weight of the oil component and is either substantially free of free fatty acids or comprises free fatty acids in an amount that is less than 20% by weight of the total weight of the oil component.
  • MAGs monoacyl glycerols
  • DAGs diacylglycerols
  • TAGs triacylglycerols
  • composition of any of the applicable embodiments of Embodiment 2, wherein the composition is an emulsion is an emulsion.
  • composition of any of the applicable embodiments of Embodiment 2 wherein the oil component comprises MAGs in an amount from about 50% to about 99% by weight of the total weight of the oil component.
  • composition of any of the applicable embodiments of Embodiment 2 wherein the oil component comprises from about 1% to about 20% by weight of the total weight of the composition.
  • composition of any of the applicable embodiments of Embodiment 2, wherein the composition is an emulsion is an emulsion.
  • composition of any of the applicable embodiments of Embodiment 2 wherein the stabilizer is selected from the group consisting of xanthan gum, gum arabic, guar gum, agar, carrageenan, locust bean gum, carboxymethylcellulose, gelatin, pectin, and starch, or any combination thereof.
  • the oil component comprises from about 5% to about 30% by weight of the total weight of the composition (and any range there between).
  • composition of any of the applicable embodiments of Embodiment 2, wherein the composition further comprises an active ingredient.
  • the local anesthetic agent is selected from the group consisting of procaine, butacaine, benzocaine, lidocaine, bupivacaine, prilocaine, tetracaine, carbocaine, chloroprocaine, etidocaine, articaine, dibucaine, piperocaine, and combinations thereof.
  • composition of any of the applicable embodiments of Embodiment 2, wherein the active ingredient is nitroglycerin.
  • a composition of any of the embodiments of Embodiment 2 for use as a personal lubricant for use as a personal lubricant.
  • a composition of any of the embodiments of Embodiment 2 for use as a lubricant on rubber materials is not limited.
  • composition of any of the embodiments of Embodiment 2 further comprising at least one additional ingredient selected from the group consisting of silicone, hyaluronic acid, aloe vera juice, butylene glycol, propylene glycol, glycerin (glycerol), dimethicone, cyclomethicone, cyclopentasiolxane, polyehtylene glycol, propanediol, polyoxyethylene, and carboxymethylcellulose, hydroxyethyl cellulose.
  • silicone hyaluronic acid
  • aloe vera juice butylene glycol
  • propylene glycol propylene glycol
  • glycerin (glycerol) dimethicone
  • cyclomethicone cyclopentasiolxane
  • polyehtylene glycol propanediol
  • polyoxyethylene polyoxyethylene
  • carboxymethylcellulose hydroxyethyl cellulose
  • composition of any of the embodiments of Embodiment 2, wherein the oil component is an EMO is an EMO.
  • Embodiment 3 A method for manufacturing a material comprising applying a composition of any of the embodiments of Embodiment 2 to the material, wherein the material is selected from the group consisting of rubber, latex rubber, polyurethane, polyisoprene, nitrile rubber, or animal intestine.
  • Embodiment 4 A method for treating feminine dryness comprising administering a suppository to a vaginal surface of a subj ect, wherein the suppository comprises or is otherwise coated with a composition of any of the embodiments of Embodiment 2.
  • Embodiment 5 A method for treating feminine dryness comprising administering a composition to a vaginal surface of a subject, wherein the composition is any of the embodiments of Embodiment 2.
  • free fatty acid oil was prepared by the complete hydrolysis of the source oil (e.g., canola, sesame, flaxseed, coconut, fractionated coconut oil (FCO), or fish oil) to FFA and glycerol followed by subsequent separation of the glycerol from the FFA oil.
  • FFA oils were prepared in a 5L stirred, j acketed glass reactor.
  • Citric acid buffer 100 mM, pH 5.8 was prepared by combining 18.5 grams of food grade citric acid with 1.50 g of food grade sodium hydroxide in 963 mL of distilled de-ionized water.
  • Amano Lipase AY (0.78 g) was dissolved in the solution which was then heated to 33°C and agitated at 300 rpm. After a brief (10 min.) vacuum degassing, 780 g of source oil was added to the reactor. The reaction volume was overlaid with nitrogen and the reaction proceeded for 24 hours until all of the TAGs had been converted to free fatty acids and glycerol. Once the reaction was complete, the mixture was heated to 70°C for 1 hour to inactivate the lipase. Agitation was stopped. After the two phases had separated, the upper phase (the free fatty acid oil) was removed and stored at 4°C in opaque plastic bottles under nitrogen. The extent of reaction was then analyzed by thin layer chromatography.
  • EMO was produced from the FFA oil through the selective re-esterification of the FFA to glycerol to form MAG and DAG.
  • FFA oil as described above was combined with 1,560 g of food grade glycerol and heated to 30°C with agitation (300 rpm). Vacuum was applied (-720 mmHg) to degas the material and remove residual water.
  • Amano Lipase G (1.56 g in 50 mL DI water) was then added to the reactor and the vacuum was reapplied (-740 mmHg). The reaction was allowed to proceed for 72 hours with progress monitored by TLC.
  • HPLC system consisted of an LC-20AD pump, SIL-20AC HT autosampler, CTO-20 A column oven, and RID-10A refractive index detector (Shimadzu Scientific Instruments, Inc.).
  • HPLC conditions were: 20 uL injection volume, isocratic elution of mobile phase consisting of 85% methanol, 10% isopropanol, and 5% hexanes, flow rate of 0.800 mL/min, and column temperature of 40 °C.
  • Column used was a SUPELCOSIL LC-18 column (250 mm x 4.6 mm; 5 um particle size). Samples were prepared in mobile phase. A mobile phase blank chromatogram was used to correct for background.
  • the retention times were 3.4-4.0 min for glycerol, 4.0-6.2 min for MAGs and FFAs, 6.3-10.8 min for DAGs, and 11.0-50.0 min for TAGs. Integration of these peaks provided relative ratios, or area-%, of glycerol, MAG+FFA, DAG, and TAG. Since the MAG and FFA peaks overlapped, FFA content was determined by titrimetry. Samples were dissolved in a solvent (95% ethanol/di ethyl ether, 1/1, v/v) and titrated to neutrality (indicated with phenolphthalein) with 0.1M KOH in ethanol. This value is reported as a weight percent.
  • MAG content was calculated by subtracting the FFA content from the MAG+FFA determined by HPLC.
  • FCO and coconut EMO Figure 17
  • isocratic elution mobile phase was modified to 75% methanol and 25% water in order to separate glycerol, MAG+FFA, and DAG peaks.
  • Table 1 below provides the relative glycerol, MAG, DAG, TAG, and FFA content of the EMOs which is used in the following Examples unless otherwise noted.
  • the method in this Example 1 for producing EMOs was used for all below examples unless otherwise noted.
  • the average burst time following treatment with baby oil was 10 seconds, which is consistent with prior literature (Rosen, A. and Rosen, T. “Study of condom integrity after brief exposure to over-the-counter vaginal preparations.” Southern Medical Journal. Vol 92, No. 3. 1999.).
  • the average burst times of untreated controls and canola EMO were similar at 84.5 and 83 seconds, respectively, indicating the canola EMO had no noticeable effect on the condom durability.
  • Condoms were removed from packaging, rinsed with water to remove external lubrication, and pat dried. A generous amount ( ⁇ 1 - 2 mL) of either canola EMO or canola FFA was applied to the condoms and allowed to sit for 30 minutes. Condoms were attached to an air compressor (Sears Craftsmen air compressor, Model 919.151360) using parafilm. Using the lowest setting, the air compressor was turned on and a stopwatch was used to record the amount of time before the condom burst. Untreated condoms were used as a control.
  • Condoms were removed from packaging, rinsed with water to remove external lubrication, and pat dried. A generous amount ( ⁇ 1 - 2 mL) of canola EMO was applied to the condoms and allowed to sit for 15 minutes. Condoms were attached to an air compressor (Sears Craftsmen air compressor, Model 919.151360) using parafilm. Using the lowest setting, the air compressor was turned on and a stopwatch was used to record the amount of time before the condom burst. Untreated condoms were used as a control.
  • Example 5 Total Burst Time for Latex Condoms With or Without Various Sesame Oil Preparations (EMO, TAG, and FFA)
  • Example 7 Total Burst Time for Latex Condoms with Sesame EMO Following Fatty Acid Reduction
  • Sesame EMOs were treated with 10 N sodium hydroxide (NaOH) to neutralize and reduce the fatty acid content.
  • NaOH sodium hydroxide
  • a “low FFA” oil is one that has been subjected to this sodium hydroxide treatment.
  • Table 1 The difference in composition of the sesame EMO before and after NaOH treatment is shown in Table 1.
  • Example 8 Total Burst Time for Latex Condoms Using Ethyl Ester and Monoacylglyceride Reagents [00168] Unexpired Durex® Extra Sensitive Extra Lubricated brand condoms were removed from packaging, rinsed with water to remove external lubrication, and pat dried.
  • Example 10 Total Burst Time for Latex Condoms Following 7 Day Exposure to Various EMOs
  • Unexpired Durex® Extra Sensitive Extra Lubricated brand condoms were removed from packaging, rinsed with water to remove external lubrication, and pat dried.
  • Glyceryl monooleate (0.3 mL pre-melted; Sigma; >99% purity) or low FFA sesame EMO (0.3 mL) was applied to the condoms and stored in plastic bag for 7 days.
  • Condoms were attached to an air compressor (Sears Craftsmen air compressor, Model 919.151360) using parafilm. Using the lowest setting, the air compressor was turned on and a stopwatch was used to record the amount of time before the condom burst.
  • Example 12 Total Burst Time for Polyurethane Condoms Exposed to Various EMOs
  • Example 13 Total Burst Time for Nitrile Rubber Female Condoms Exposed to Various EMOs
  • Unexpired FC2 female condom brand condoms were removed from packaging, rinsed with water to remove external lubrication, and pat dried. Sesame EMO (1 mL) or no FFA sesame EMO (1 mL) was applied to the condoms and allowed to sit for 15 minutes. Condoms were attached to an air compressor (Sears Craftsmen air compressor, Model 919.151360) using parafilm. Using the lowest setting, the air compressor was turned on and a stopwatch was used to record the amount of time before the condom burst. Untreated condoms were used as a control. The results are provided in Figure 14. There was no significant difference in burst times among the samples compared to untreated controls, indicating compatibility with nitrile rubber.
  • Emulsions were prepared by weighing oil phase (EMO) and aqueous phase (water) separately, and heating each at 60 °C. The aqueous phase was added to the oil phase and immediately subjected to high-sheer homogenization for 30 seconds to produce a coarse, milky emulsion. For samples containing xanthan gum, xanthan gum was added to the emulsion and re-homogenized for at least 30 seconds. The final concentration of the xanthan gum was 0.6%.
  • NRL and PU substrates were treated with no FFA sesame EMO and sesame EMO for 3 hours.
  • the results are shown in Table 2. Consistent with the results from the burst tests, NRL had minimal swelling and no change in length with either EMO. However, PU substrates swelled more in the sesame EMO compared to the no FFA sesame EMO. These results are consistent with the burst tests, where the sesame EMO significantly reduced the burst time of PU condoms. Table 2. The percent (%) change in mass and length of NRL and PU substrates after 3 hours immersion in no FFA sesame EMO or sesame EMO.
  • NRL substrates were treated with silicone oil control, low FFA sesame EMO emulsion (5% EMO), moderate FFA sesame EMO emulsion (8% EMO), or sesame EMO emulsion (10% EMO) for 3 hours and 1 week.
  • the results are shown in Table 4.
  • the samples had minimal effects on substrate swelling.
  • the emulsions with higher FFA content resulted in more swelling than the low FFA emulsion, likely due to the differences in FFA concentration.
  • Table 4 The percent (%) change in mass and length of NRL substrates after 3 hours and 1 week immersion in silicone oil, low FFA sesame EMO emulsion, moderate FFA sesame EMO emulsion, or sesame EMO emulsion.
  • NRL, PU, and NBR substrates were treated with silicone oil control, low FFA sesame EMO emulsion (5% EMO), or moderate FFA sesame EMO emulsion (8% EMO) for 3 hours and 1 week.
  • the results are shown in Tables 5-7. All samples had minimal effects on substrate swelling over 3 hours, indicating good compatibility for short term application.
  • the low FFA sesame EMO emulsion had minimal swelling in NRL after 1 week, indicating good compatibility with NRL.
  • Table 5 The percent (%) change in mass and length of NRL substrates after 3 hours immersion in
  • Table 6 The percent (%) change in mass and length of PU substrates after 3 hours immersion in silicone oil, low FFA sesame EMO emulsion, or moderate FFA sesame EMO emulsion.
  • Table 7 The percent (%) change in mass and length of NBR substrates after 3 hours immersion in silicone oil, low FFA sesame EMO emulsion, or moderate FFA sesame EMO emulsion.

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Abstract

L'invention concerne des compositions d'huile destinées à être utilisées dans divers produits de soins personnels tels que des préservatifs en latex et des lubrifiants personnels. Les compositions d'huile sont formulées pour être compatibles avec une administration topique sur la peau et les tissus muqueux ainsi qu'avec des matériaux de caoutchouc tels que le caoutchouc de latex, le caoutchouc nitrile, le polyuréthane et le polyisoprène.
PCT/US2024/043335 2023-08-22 2024-08-22 Compositions à base d'huile compatibles avec le latex Pending WO2025043046A1 (fr)

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7748240B1 (en) * 2009-03-04 2010-07-06 James Paul Cherneski Foot gripping garment
US20100215708A1 (en) * 2006-06-29 2010-08-26 Andreas Zumbuehl Coating of devices with effector compounds
WO2011061330A2 (fr) * 2009-11-20 2011-05-26 Symrise Ag Utilisation d'agents rafraîchissants physiologiques et produits contenant de tels agents
US20130071930A1 (en) * 2010-01-25 2013-03-21 University Of Pittsburgh - Of The Commonwealth System Of Higher Education Polyesters, methods of making polyesters and uses therefor
US20180064645A1 (en) * 2016-07-28 2018-03-08 Allen Greenspoon Novel Orally Administrable Formulation
US20180310566A1 (en) * 2017-04-29 2018-11-01 Nevada Naturals Inc. Biofilm Penetrating Compositions and Methods
WO2019018656A1 (fr) * 2017-07-19 2019-01-24 Ironwood Pharmaceuticals, Inc. Efficacité d'une forme posologique d'agent séquestrant d'acide biliaire à rétention gastrique

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100215708A1 (en) * 2006-06-29 2010-08-26 Andreas Zumbuehl Coating of devices with effector compounds
US7748240B1 (en) * 2009-03-04 2010-07-06 James Paul Cherneski Foot gripping garment
WO2011061330A2 (fr) * 2009-11-20 2011-05-26 Symrise Ag Utilisation d'agents rafraîchissants physiologiques et produits contenant de tels agents
US20130071930A1 (en) * 2010-01-25 2013-03-21 University Of Pittsburgh - Of The Commonwealth System Of Higher Education Polyesters, methods of making polyesters and uses therefor
US20180064645A1 (en) * 2016-07-28 2018-03-08 Allen Greenspoon Novel Orally Administrable Formulation
US20180310566A1 (en) * 2017-04-29 2018-11-01 Nevada Naturals Inc. Biofilm Penetrating Compositions and Methods
WO2019018656A1 (fr) * 2017-07-19 2019-01-24 Ironwood Pharmaceuticals, Inc. Efficacité d'une forme posologique d'agent séquestrant d'acide biliaire à rétention gastrique

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