CA3091186C - Compositions a base de nanoemulsions, procedes de leur preparation et leur utilisation dans la livraison d`ingredients actifs - Google Patents
Compositions a base de nanoemulsions, procedes de leur preparation et leur utilisation dans la livraison d`ingredients actifs Download PDFInfo
- Publication number
- CA3091186C CA3091186C CA3091186A CA3091186A CA3091186C CA 3091186 C CA3091186 C CA 3091186C CA 3091186 A CA3091186 A CA 3091186A CA 3091186 A CA3091186 A CA 3091186A CA 3091186 C CA3091186 C CA 3091186C
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- 239000000203 mixture Substances 0.000 title claims abstract description 367
- 239000007908 nanoemulsion Substances 0.000 title claims abstract description 186
- 239000004480 active ingredient Substances 0.000 title claims abstract description 142
- 238000000034 method Methods 0.000 title claims abstract description 100
- 238000002360 preparation method Methods 0.000 title claims abstract description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 162
- 150000002632 lipids Chemical class 0.000 claims abstract description 129
- 239000007788 liquid Substances 0.000 claims abstract description 94
- 239000007787 solid Substances 0.000 claims abstract description 53
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 52
- 239000003921 oil Substances 0.000 claims description 285
- 235000019198 oils Nutrition 0.000 claims description 282
- 229940060184 oil ingredients Drugs 0.000 claims description 281
- 239000012071 phase Substances 0.000 claims description 146
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 120
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 83
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 78
- 235000019271 petrolatum Nutrition 0.000 claims description 63
- 239000004264 Petrolatum Substances 0.000 claims description 62
- 229940066842 petrolatum Drugs 0.000 claims description 62
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 60
- 239000002202 Polyethylene glycol Substances 0.000 claims description 55
- 229920001223 polyethylene glycol Polymers 0.000 claims description 55
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims description 54
- 229940075529 glyceryl stearate Drugs 0.000 claims description 52
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims description 48
- 235000011187 glycerol Nutrition 0.000 claims description 41
- 229920000058 polyacrylate Polymers 0.000 claims description 41
- 229960000541 cetyl alcohol Drugs 0.000 claims description 39
- 239000003755 preservative agent Substances 0.000 claims description 39
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 38
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 38
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 38
- 239000005642 Oleic acid Substances 0.000 claims description 38
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 38
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 claims description 38
- 229920001577 copolymer Polymers 0.000 claims description 38
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 38
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 38
- 229940100460 peg-100 stearate Drugs 0.000 claims description 38
- 229920000642 polymer Polymers 0.000 claims description 38
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 36
- 239000004322 Butylated hydroxytoluene Substances 0.000 claims description 36
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 36
- 239000008346 aqueous phase Substances 0.000 claims description 36
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims description 36
- 229940095259 butylated hydroxytoluene Drugs 0.000 claims description 36
- 239000004359 castor oil Substances 0.000 claims description 36
- 235000019438 castor oil Nutrition 0.000 claims description 36
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 36
- AEIJTFQOBWATKX-UHFFFAOYSA-N octane-1,2-diol Chemical group CCCCCCC(O)CO AEIJTFQOBWATKX-UHFFFAOYSA-N 0.000 claims description 36
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims description 35
- 229960001259 diclofenac Drugs 0.000 claims description 34
- 239000003814 drug Substances 0.000 claims description 34
- 229940115478 isopropyl lauroyl sarcosinate Drugs 0.000 claims description 34
- XLCIFRJORZNGEV-UHFFFAOYSA-N propan-2-yl 2-[dodecanoyl(methyl)amino]acetate Chemical compound CCCCCCCCCCCC(=O)N(C)CC(=O)OC(C)C XLCIFRJORZNGEV-UHFFFAOYSA-N 0.000 claims description 34
- 239000003963 antioxidant agent Substances 0.000 claims description 33
- 239000003974 emollient agent Substances 0.000 claims description 31
- 239000003961 penetration enhancing agent Substances 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 30
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 claims description 29
- 229960005323 phenoxyethanol Drugs 0.000 claims description 29
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 28
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 claims description 28
- 239000003906 humectant Substances 0.000 claims description 28
- 230000002335 preservative effect Effects 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 28
- 230000003078 antioxidant effect Effects 0.000 claims description 27
- 229960004194 lidocaine Drugs 0.000 claims description 27
- ZTGXAWYVTLUPDT-UHFFFAOYSA-N cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CC=C(C)C1 ZTGXAWYVTLUPDT-UHFFFAOYSA-N 0.000 claims description 26
- QHMBSVQNZZTUGM-UHFFFAOYSA-N Trans-Cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CCC(C)=C1 QHMBSVQNZZTUGM-UHFFFAOYSA-N 0.000 claims description 25
- QHMBSVQNZZTUGM-ZWKOTPCHSA-N cannabidiol Chemical compound OC1=CC(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)=C)CCC(C)=C1 QHMBSVQNZZTUGM-ZWKOTPCHSA-N 0.000 claims description 25
- 229950011318 cannabidiol Drugs 0.000 claims description 25
- 239000002738 chelating agent Substances 0.000 claims description 25
- PCXRACLQFPRCBB-ZWKOTPCHSA-N dihydrocannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)C)CCC(C)=C1 PCXRACLQFPRCBB-ZWKOTPCHSA-N 0.000 claims description 25
- 229960001193 diclofenac sodium Drugs 0.000 claims description 24
- JGMJQSFLQWGYMQ-UHFFFAOYSA-M sodium;2,6-dichloro-n-phenylaniline;acetate Chemical compound [Na+].CC([O-])=O.ClC1=CC=CC(Cl)=C1NC1=CC=CC=C1 JGMJQSFLQWGYMQ-UHFFFAOYSA-M 0.000 claims description 24
- 238000013329 compounding Methods 0.000 claims description 22
- 239000000341 volatile oil Substances 0.000 claims description 21
- CYQFCXCEBYINGO-UHFFFAOYSA-N THC Natural products C1=C(C)CCC2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3C21 CYQFCXCEBYINGO-UHFFFAOYSA-N 0.000 claims description 20
- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical group C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 claims description 20
- 229960004242 dronabinol Drugs 0.000 claims description 20
- 229960005274 benzocaine Drugs 0.000 claims description 19
- 150000003505 terpenes Chemical class 0.000 claims description 19
- 229960002372 tetracaine Drugs 0.000 claims description 19
- GKCBAIGFKIBETG-UHFFFAOYSA-N tetracaine Chemical compound CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 GKCBAIGFKIBETG-UHFFFAOYSA-N 0.000 claims description 19
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 claims description 18
- 230000000202 analgesic effect Effects 0.000 claims description 18
- 235000013871 bee wax Nutrition 0.000 claims description 18
- 239000012166 beeswax Substances 0.000 claims description 18
- 229940092738 beeswax Drugs 0.000 claims description 18
- FLPJVCMIKUWSDR-UHFFFAOYSA-N 2-(4-formylphenoxy)acetamide Chemical compound NC(=O)COC1=CC=C(C=O)C=C1 FLPJVCMIKUWSDR-UHFFFAOYSA-N 0.000 claims description 15
- 229940074979 cetyl palmitate Drugs 0.000 claims description 15
- PXDJXZJSCPSGGI-UHFFFAOYSA-N hexadecanoic acid hexadecyl ester Natural products CCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC PXDJXZJSCPSGGI-UHFFFAOYSA-N 0.000 claims description 15
- 230000003444 anaesthetic effect Effects 0.000 claims description 14
- 150000002191 fatty alcohols Chemical class 0.000 claims description 14
- 238000002156 mixing Methods 0.000 claims description 14
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 14
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- 239000013543 active substance Substances 0.000 claims description 13
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 13
- 229920001400 block copolymer Polymers 0.000 claims description 12
- 239000008172 hydrogenated vegetable oil Substances 0.000 claims description 12
- 239000002480 mineral oil Substances 0.000 claims description 12
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 12
- 235000010446 mineral oil Nutrition 0.000 claims description 11
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 claims description 9
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 claims description 9
- FETSQPAGYOVAQU-UHFFFAOYSA-N glyceryl palmitostearate Chemical compound OCC(O)CO.CCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O FETSQPAGYOVAQU-UHFFFAOYSA-N 0.000 claims description 9
- 229940046813 glyceryl palmitostearate Drugs 0.000 claims description 9
- 229920001983 poloxamer Polymers 0.000 claims description 9
- 229960001777 castor oil Drugs 0.000 claims description 8
- XEFAJZOBODPHBG-SSDOTTSWSA-N (1R)-1-phenoxyethanol Chemical compound O(C1=CC=CC=C1)[C@H](C)O XEFAJZOBODPHBG-SSDOTTSWSA-N 0.000 claims description 6
- 229920001451 polypropylene glycol Polymers 0.000 claims description 6
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 claims description 5
- 229960000502 poloxamer Drugs 0.000 claims description 5
- BYNVYIUJKRRNNC-UHFFFAOYSA-N docosanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.CCCCCCCCCCCCCCCCCCCCCC(O)=O BYNVYIUJKRRNNC-UHFFFAOYSA-N 0.000 claims 16
- BDOYKFSQFYNPKF-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetic acid;sodium Chemical compound [Na].[Na].OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O BDOYKFSQFYNPKF-UHFFFAOYSA-N 0.000 claims 14
- 239000006071 cream Substances 0.000 description 50
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- 210000003491 skin Anatomy 0.000 description 25
- DMBUODUULYCPAK-UHFFFAOYSA-N 1,3-bis(docosanoyloxy)propan-2-yl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCCCCCC DMBUODUULYCPAK-UHFFFAOYSA-N 0.000 description 24
- 239000000843 powder Substances 0.000 description 21
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 16
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 15
- 239000000839 emulsion Substances 0.000 description 15
- WEEGYLXZBRQIMU-UHFFFAOYSA-N Eucalyptol Chemical compound C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 14
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- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 14
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- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 12
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- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
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- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- 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
- A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
- A61K31/245—Amino benzoic acid types, e.g. procaine, novocaine
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- 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
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- 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
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
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- 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
- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
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- Health & Medical Sciences (AREA)
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- Emergency Medicine (AREA)
- Pain & Pain Management (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Abstract
Il est décrit des compositions qui consistent en une nano-émulsion dhuile et deau propagée dans une phase huileuse externe, des modes de préparation de ces compositions ainsi que des modes dutilisation de ces compositions, comme la libération dingrédients actifs dans un sujet. Les méthodes comprennent la combinaison dun premier mélange composé dune huile à létat liquide et dun lipide chargé à un deuxième mélange aqueux constitué dun émulsifiant thermoréversible qui forme un film en vue de préparer une nano-émulsion dhuile et deau, suivie par la combinaison de la nano-émulsion dhuile et deau à un troisième mélange composé dune combinaison de lipides à létat solide en vue de préparer la composition.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA3091186A CA3091186C (fr) | 2020-08-26 | 2020-08-26 | Compositions a base de nanoemulsions, procedes de leur preparation et leur utilisation dans la livraison d`ingredients actifs |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA3091186A CA3091186C (fr) | 2020-08-26 | 2020-08-26 | Compositions a base de nanoemulsions, procedes de leur preparation et leur utilisation dans la livraison d`ingredients actifs |
Publications (2)
Publication Number | Publication Date |
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CA3091186A1 CA3091186A1 (fr) | 2020-10-26 |
CA3091186C true CA3091186C (fr) | 2022-02-08 |
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CA3091186A Active CA3091186C (fr) | 2020-08-26 | 2020-08-26 | Compositions a base de nanoemulsions, procedes de leur preparation et leur utilisation dans la livraison d`ingredients actifs |
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CA (1) | CA3091186C (fr) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP4112042A1 (fr) * | 2021-06-30 | 2023-01-04 | GSK Consumer Healthcare SARL | Nanoémulsion comprenant du diclofénac |
CN114681351A (zh) * | 2022-04-01 | 2022-07-01 | 广州市娇兰化妆品有限公司 | 一种具有三重作用的类神经酰胺提取物的纳米乳液及其制备方法与应用 |
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2020
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