ZA200306204B - Injectable water-in-oil emulsions. - Google Patents
Injectable water-in-oil emulsions. Download PDFInfo
- Publication number
- ZA200306204B ZA200306204B ZA200306204A ZA200306204A ZA200306204B ZA 200306204 B ZA200306204 B ZA 200306204B ZA 200306204 A ZA200306204 A ZA 200306204A ZA 200306204 A ZA200306204 A ZA 200306204A ZA 200306204 B ZA200306204 B ZA 200306204B
- Authority
- ZA
- South Africa
- Prior art keywords
- oil
- water
- emulsion
- emulsifier
- emulsions
- Prior art date
Links
- 239000000839 emulsion Substances 0.000 title claims abstract description 55
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 41
- -1 Xanthan polysaccharide Chemical class 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 8
- 238000009472 formulation Methods 0.000 claims abstract description 5
- 239000002671 adjuvant Substances 0.000 claims description 45
- 239000007762 w/o emulsion Substances 0.000 claims description 42
- 229960005486 vaccine Drugs 0.000 claims description 30
- NWGKJDSIEKMTRX-BFWOXRRGSA-N [(2r)-2-[(3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] (z)-octadec-9-enoate Chemical group CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)C1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-BFWOXRRGSA-N 0.000 claims description 23
- 239000008346 aqueous phase Substances 0.000 claims description 17
- 238000012790 confirmation Methods 0.000 claims description 15
- 229920001400 block copolymer Polymers 0.000 claims description 10
- 230000000890 antigenic effect Effects 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000012678 infectious agent Substances 0.000 claims description 5
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 5
- BARWIPMJPCRCTP-CLFAGFIQSA-N oleyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC BARWIPMJPCRCTP-CLFAGFIQSA-N 0.000 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- BARWIPMJPCRCTP-UHFFFAOYSA-N oleic acid oleyl ester Natural products CCCCCCCCC=CCCCCCCCCOC(=O)CCCCCCCC=CCCCCCCCC BARWIPMJPCRCTP-UHFFFAOYSA-N 0.000 claims 1
- 239000003921 oil Substances 0.000 abstract description 80
- 239000004094 surface-active agent Substances 0.000 abstract description 10
- 239000002537 cosmetic Substances 0.000 abstract description 2
- 229920001282 polysaccharide Polymers 0.000 abstract 2
- 239000005017 polysaccharide Substances 0.000 abstract 2
- 239000003381 stabilizer Substances 0.000 abstract 2
- 229920001285 xanthan gum Polymers 0.000 abstract 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 229930006000 Sucrose Natural products 0.000 abstract 1
- 239000006071 cream Substances 0.000 abstract 1
- 239000000499 gel Substances 0.000 abstract 1
- 150000004676 glycans Chemical class 0.000 abstract 1
- 239000006210 lotion Substances 0.000 abstract 1
- 210000004080 milk Anatomy 0.000 abstract 1
- 235000013336 milk Nutrition 0.000 abstract 1
- 239000012875 nonionic emulsifier Substances 0.000 abstract 1
- 238000000518 rheometry Methods 0.000 abstract 1
- 239000005720 sucrose Substances 0.000 abstract 1
- 239000002562 thickening agent Substances 0.000 abstract 1
- 235000019198 oils Nutrition 0.000 description 70
- 239000012071 phase Substances 0.000 description 46
- 239000000427 antigen Substances 0.000 description 16
- 102000036639 antigens Human genes 0.000 description 16
- 108091007433 antigens Proteins 0.000 description 16
- 238000002347 injection Methods 0.000 description 12
- 239000007924 injection Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 239000002480 mineral oil Substances 0.000 description 11
- 241000711404 Avian avulavirus 1 Species 0.000 description 10
- 241000711450 Infectious bronchitis virus Species 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 241000700605 Viruses Species 0.000 description 9
- 210000002966 serum Anatomy 0.000 description 9
- 230000035931 haemagglutination Effects 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 7
- 238000004090 dissolution Methods 0.000 description 7
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 7
- 229940093471 ethyl oleate Drugs 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000002953 phosphate buffered saline Substances 0.000 description 7
- 238000002255 vaccination Methods 0.000 description 7
- 238000010790 dilution Methods 0.000 description 6
- 239000012895 dilution Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 238000013112 stability test Methods 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 206010024769 Local reaction Diseases 0.000 description 5
- PWEOPMBMTXREGV-UHFFFAOYSA-N decanoic acid;octanoic acid;propane-1,2-diol Chemical compound CC(O)CO.CCCCCCCC(O)=O.CCCCCCCC(O)=O.CCCCCCCCCC(O)=O.CCCCCCCCCC(O)=O PWEOPMBMTXREGV-UHFFFAOYSA-N 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 235000010446 mineral oil Nutrition 0.000 description 5
- 229940031709 peg-30-dipolyhydroxystearate Drugs 0.000 description 5
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 5
- 239000008307 w/o/w-emulsion Substances 0.000 description 5
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 239000008363 phosphate buffer Substances 0.000 description 4
- 241000271566 Aves Species 0.000 description 3
- 241000287828 Gallus gallus Species 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 235000013330 chicken meat Nutrition 0.000 description 3
- 239000000084 colloidal system Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000004945 emulsification Methods 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 238000000265 homogenisation Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 230000028993 immune response Effects 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 239000007764 o/w emulsion Substances 0.000 description 3
- 229960004063 propylene glycol Drugs 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- 230000003612 virological effect Effects 0.000 description 3
- 229940114072 12-hydroxystearic acid Drugs 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000010775 animal oil Substances 0.000 description 2
- 230000000840 anti-viral effect Effects 0.000 description 2
- 230000002238 attenuated effect Effects 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000000481 breast Anatomy 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- 230000001492 haemagglutinating effect Effects 0.000 description 2
- 230000003053 immunization Effects 0.000 description 2
- 238000002649 immunization Methods 0.000 description 2
- 230000002163 immunogen Effects 0.000 description 2
- 238000000386 microscopy Methods 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 229920001983 poloxamer Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000009589 serological test Methods 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- JDRAOGVAQOVDEB-KTKRTIGZSA-N (3-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl) (z)-octadec-9-enoate Chemical compound OC1COC2C(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC21 JDRAOGVAQOVDEB-KTKRTIGZSA-N 0.000 description 1
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 1
- KMUBFTBPGVULKC-UHFFFAOYSA-N 2-hexyldecyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC(CCCCCC)CCCCCCCC KMUBFTBPGVULKC-UHFFFAOYSA-N 0.000 description 1
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- ZAKOWWREFLAJOT-UHFFFAOYSA-N d-alpha-Tocopheryl acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940090854 hexyldecyl laurate Drugs 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000003308 immunostimulating effect Effects 0.000 description 1
- 229940031551 inactivated vaccine Drugs 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229940074928 isopropyl myristate Drugs 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
- 235000008935 nutritious Nutrition 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical class CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000008251 pharmaceutical emulsion Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 229940031439 squalene Drugs 0.000 description 1
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 229940031626 subunit vaccine Drugs 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229940042585 tocopherol acetate Drugs 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
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
- A61K47/06—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
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/39—Medicinal preparations containing antigens or antibodies characterised by the immunostimulating additives, e.g. chemical adjuvants
-
- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K2039/555—Medicinal preparations containing antigens or antibodies characterised by a specific combination antigen/adjuvant
- A61K2039/55511—Organic adjuvants
- A61K2039/55566—Emulsions, e.g. Freund's adjuvant, MF59
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Mycology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Immunology (AREA)
- Microbiology (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Medicinal Preparation (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Colloid Chemistry (AREA)
- Cosmetics (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01200745 | 2001-02-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200306204B true ZA200306204B (en) | 2004-09-09 |
Family
ID=8179948
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200306204A ZA200306204B (en) | 2001-02-28 | 2003-08-11 | Injectable water-in-oil emulsions. |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US8496939B2 (da) |
| EP (1) | EP1367997B1 (da) |
| JP (1) | JP4057423B2 (da) |
| AT (1) | ATE438382T1 (da) |
| AU (1) | AU2002253085B2 (da) |
| BR (1) | BR0207698A (da) |
| CA (1) | CA2438692C (da) |
| DE (1) | DE60233206D1 (da) |
| DK (1) | DK1367997T3 (da) |
| ES (1) | ES2331058T3 (da) |
| MX (1) | MXPA03007766A (da) |
| WO (1) | WO2002067899A1 (da) |
| ZA (1) | ZA200306204B (da) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2822834B1 (fr) * | 2001-04-02 | 2005-02-25 | Flamel Tech Sa | Suspension colloidale de nanoparticules a base de copolymeres amphiphile pour la vectorisation de principes actifs et leur mode de preparation |
| FR2840614B1 (fr) * | 2002-06-07 | 2004-08-27 | Flamel Tech Sa | Polyaminoacides fonctionnalises par de l'alpha-tocopherol et leurs applications notamment therapeutiques |
| FR2843117B1 (fr) * | 2002-07-30 | 2004-10-15 | Flamel Tech Sa | Polyaminoacides fonctionnalises par au moins un groupement hydrophobe et leurs applications notamment therapeutiques |
| FR2860516B1 (fr) * | 2003-10-03 | 2006-01-13 | Flamel Tech Sa | Homopolyaminoacides telecheliques fonctionnalises par des groupements hydrophobes et leurs applications notamment therapeutiques |
| FR2860717B1 (fr) * | 2003-10-13 | 2006-02-03 | Ethypharm Sa | Compositions de particules lipidiques solides monodisperses |
| FR2862536B1 (fr) * | 2003-11-21 | 2007-11-23 | Flamel Tech Sa | Formulations pharmaceutiques pour la liberation prolongee de principe(s) actif(s), ainsi que leurs applications notamment therapeutiques |
| US7485451B2 (en) * | 2004-11-18 | 2009-02-03 | Regents Of The University Of California | Storage stable compositions of biological materials |
| FR2878746B1 (fr) * | 2004-12-02 | 2007-02-23 | Vetoquinol Sa Sa | Nouvelle composition pharmaceutique utilisable dans le domaine des vaccins |
| FR2903602B1 (fr) * | 2006-07-12 | 2012-10-26 | Seppic Sa | Formulation injectable a liberation prolongee de principes actifs, procede pour sa preparation |
| FR2910318B1 (fr) * | 2006-12-20 | 2009-07-03 | Flamel Technologies Sa | Dispersion de polyaminoacides dans une phase lipidique continue. |
| SG193821A1 (en) | 2008-08-29 | 2013-10-30 | Boehringer Ingelheim Vetmed | West nile virus vaccine |
| EP2361286A4 (en) | 2008-12-22 | 2012-05-23 | Henkel Ag & Co Kgaa | WATER-BASED CLEANING AGENT FOR CLEANING COLORS ON SOLVENT BASIS |
| BR112013023354B1 (pt) | 2011-03-14 | 2022-02-15 | Boehringer Ingelheim Animal Health Usa Inc | Composição imunogênica compreendendo cepas de vírus da rinite equina a (erav) e seu método de produção |
| ES2825823T3 (es) * | 2011-06-10 | 2021-05-17 | Indorama Ventures Oxides Australia Pty Ltd | Agentes estructurantes y emulsionantes para formulaciones agrícolas a base de aceite |
| EP2666789A1 (en) | 2012-05-21 | 2013-11-27 | Basf Se | Inverse dispersion comprising an anionic or a nonionic polymer and a stabilizing agent |
| US9102900B2 (en) | 2012-05-21 | 2015-08-11 | Basf Se | Inverse dispersion comprising a cationic polymer and a stabilizing agent |
| WO2013174622A1 (en) | 2012-05-21 | 2013-11-28 | Basf Se | Inverse dispersion comprising a cationic polymer and a stabilizing agent |
| WO2016014733A1 (en) | 2014-07-23 | 2016-01-28 | The Procter & Gamble Company | Fabric and home care treatment compositions |
| JP6542350B2 (ja) | 2014-07-23 | 2019-07-10 | ザ プロクター アンド ギャンブル カンパニーＴｈｅ Ｐｒｏｃｔｅｒ ＆ Ｇａｍｂｌｅ Ｃｏｍｐａｎｙ | 布地ケア及びホームケア処理組成物 |
| WO2016014802A1 (en) | 2014-07-23 | 2016-01-28 | The Procter & Gamble Company | Fabric and home care treatment compositions |
| EP3172300B1 (en) | 2014-07-23 | 2018-12-26 | The Procter and Gamble Company | Fabric and home care treatment composition |
| WO2016014744A1 (en) | 2014-07-23 | 2016-01-28 | The Procter & Gamble Company | Fabric and home care treatment compositions |
| MX2017000980A (es) | 2014-07-23 | 2017-04-27 | Procter & Gamble | Composiciones de tratamiento. |
| WO2016014732A1 (en) | 2014-07-23 | 2016-01-28 | The Procter & Gamble Company | Fabric and home care treatment compositions |
| CN107072836B (zh) | 2014-11-06 | 2021-03-16 | 宝洁公司 | 用于制备图案化开孔纤维网的方法 |
| GB201506948D0 (en) | 2015-04-23 | 2015-06-10 | Croda Int Plc | Emulsions for injectable formulations |
| CA3011431C (en) | 2016-01-25 | 2021-06-01 | The Procter & Gamble Company | Fabric treatment compositions, their manufacture and use |
| MX2018009047A (es) | 2016-01-25 | 2018-11-09 | Procter & Gamble | Composiciones de tratamiento. |
| EP4056158B1 (en) | 2017-02-16 | 2024-03-06 | The Procter & Gamble Company | Absorbent articles with substrates having repeating patterns of apertures comprising a plurality of repeat units |
| CA3114485A1 (en) | 2018-10-16 | 2020-04-23 | Intervet International B.V. | Emulsion vaccine for fish |
| WO2020078958A1 (en) | 2018-10-16 | 2020-04-23 | Intervet International B.V. | Stable emulsions of bacterial antigens |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0000424B1 (en) * | 1977-07-12 | 1984-02-01 | Imperial Chemical Industries Plc | Linear or branched ester-ether block copolymers and their use as surfactants either alone or in blends with conventional surfactants |
| US4806350A (en) * | 1986-04-18 | 1989-02-21 | Norden Laboratories, Inc. | Vaccine formulation |
| JP2549118B2 (ja) * | 1987-05-30 | 1996-10-30 | 三省製薬株式会社 | 乳化組成物 |
| WO1990014837A1 (en) * | 1989-05-25 | 1990-12-13 | Chiron Corporation | Adjuvant formulation comprising a submicron oil droplet emulsion |
| DE3939492A1 (de) * | 1989-11-29 | 1991-06-06 | Mack Chem Pharm | Pharmazeutische zubereitungen |
| US5622649A (en) * | 1991-06-27 | 1997-04-22 | Emory University | Multiple emulsions and methods of preparation |
| FR2702373B1 (fr) * | 1993-03-08 | 1996-06-07 | Rhone Merieux | Emulsions vaccinales fluides eau-dans-l'huile contenant une huile métabolisable. |
| FR2706766B1 (fr) * | 1993-06-21 | 1995-08-18 | Oreal | Compositions cosmetiques filtrantes contenant un agent hydrophile comportant au moins un radical acide |
| US5646212A (en) * | 1994-09-02 | 1997-07-08 | Ici Americas Inc. | Polyalkylene glycol anhydroxy carboxylic acid dispersant |
| FR2768337B1 (fr) * | 1997-09-16 | 1999-10-15 | Oreal | Emulsions triples du type e/h/e contenant un systeme photoprotecteur capable de filtrer les rayons uv; leurs utilisations en cosmetique |
| US5935589A (en) * | 1997-10-17 | 1999-08-10 | Chesebrough-Pond's Usa Co. | Stable cosmetic compositions with different pH emulsions |
| DE19749618A1 (de) * | 1997-11-10 | 1999-05-12 | Basf Ag | Verwendung von W/O-Emulsionen als Verdicker in kosmetischen und pharmazeutischen Zubereitungen |
| US6174846B1 (en) * | 1997-12-18 | 2001-01-16 | Lever Brothers Company, A Division Of Conopco, Inc. | Liquid composition with enhanced low temperature stability |
| US20030083231A1 (en) * | 1998-11-24 | 2003-05-01 | Ahlem Clarence N. | Blood cell deficiency treatment method |
| KR100674058B1 (ko) | 1998-12-05 | 2007-01-25 | 임페리알 케미칼 인더스트리즈 피엘씨 | 유화 시스템 및 에멀젼 |
| KR100435921B1 (ko) * | 2000-12-29 | 2004-06-12 | 주식회사 태평양 | 동수역학적 이중 안정화에 의한 안정한 수-유-수 다중에멀젼 시스템 및 이의 제조방법 |
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2002
- 2002-02-26 ES ES02722157T patent/ES2331058T3/es not_active Expired - Lifetime
- 2002-02-26 CA CA2438692A patent/CA2438692C/en not_active Expired - Fee Related
- 2002-02-26 JP JP2002567267A patent/JP4057423B2/ja not_active Expired - Fee Related
- 2002-02-26 MX MXPA03007766A patent/MXPA03007766A/es active IP Right Grant
- 2002-02-26 AT AT02722157T patent/ATE438382T1/de not_active IP Right Cessation
- 2002-02-26 EP EP02722157A patent/EP1367997B1/en not_active Expired - Lifetime
- 2002-02-26 US US10/469,391 patent/US8496939B2/en not_active Expired - Fee Related
- 2002-02-26 BR BR0207698-5A patent/BR0207698A/pt not_active Application Discontinuation
- 2002-02-26 WO PCT/EP2002/002145 patent/WO2002067899A1/en active Search and Examination
- 2002-02-26 DK DK02722157T patent/DK1367997T3/da active
- 2002-02-26 DE DE60233206T patent/DE60233206D1/de not_active Expired - Lifetime
- 2002-02-26 AU AU2002253085A patent/AU2002253085B2/en not_active Ceased
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2003
- 2003-08-11 ZA ZA200306204A patent/ZA200306204B/en unknown
Also Published As
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| US20040071716A1 (en) | 2004-04-15 |
| JP2004523551A (ja) | 2004-08-05 |
| CA2438692C (en) | 2010-04-27 |
| EP1367997B1 (en) | 2009-08-05 |
| US8496939B2 (en) | 2013-07-30 |
| DE60233206D1 (de) | 2009-09-17 |
| MXPA03007766A (es) | 2004-03-16 |
| CA2438692A1 (en) | 2002-09-06 |
| JP4057423B2 (ja) | 2008-03-05 |
| ATE438382T1 (de) | 2009-08-15 |
| AU2002253085B2 (en) | 2006-03-09 |
| BR0207698A (pt) | 2004-04-20 |
| WO2002067899A1 (en) | 2002-09-06 |
| EP1367997A1 (en) | 2003-12-10 |
| DK1367997T3 (da) | 2009-11-30 |
| ES2331058T3 (es) | 2009-12-21 |
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