WO1995031956A1 - Antibacterial oil-in-water emulsions - Google Patents
Antibacterial oil-in-water emulsions Download PDFInfo
- Publication number
- WO1995031956A1 WO1995031956A1 PCT/US1995/006234 US9506234W WO9531956A1 WO 1995031956 A1 WO1995031956 A1 WO 1995031956A1 US 9506234 W US9506234 W US 9506234W WO 9531956 A1 WO9531956 A1 WO 9531956A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- oil
- glycerol
- emulsion
- antibacterial
- group
- Prior art date
Links
- 239000000839 emulsion Substances 0.000 title claims abstract description 100
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 37
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 claims abstract description 77
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 claims abstract description 77
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims abstract description 64
- 241000590002 Helicobacter pylori Species 0.000 claims abstract description 37
- 229940037467 helicobacter pylori Drugs 0.000 claims abstract description 37
- -1 glycerol ester Chemical class 0.000 claims abstract description 34
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 claims abstract description 30
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 claims abstract description 30
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 20
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 239000007764 o/w emulsion Substances 0.000 claims abstract description 11
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 5
- 239000003921 oil Substances 0.000 claims description 46
- 239000012071 phase Substances 0.000 claims description 44
- 229960001927 cetylpyridinium chloride Drugs 0.000 claims description 41
- YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 claims description 41
- 241000894006 Bacteria Species 0.000 claims description 30
- 235000019198 oils Nutrition 0.000 claims description 25
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 20
- 229930182558 Sterol Natural products 0.000 claims description 19
- 235000003702 sterols Nutrition 0.000 claims description 19
- 150000003432 sterols Chemical class 0.000 claims description 19
- 150000002632 lipids Chemical group 0.000 claims description 18
- 239000008346 aqueous phase Substances 0.000 claims description 17
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 239000003549 soybean oil Substances 0.000 claims description 13
- 235000012424 soybean oil Nutrition 0.000 claims description 13
- 235000012000 cholesterol Nutrition 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims description 10
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 9
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 9
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 9
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000005642 Oleic acid Substances 0.000 claims description 9
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 9
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 9
- ARIWANIATODDMH-AWEZNQCLSA-N 1-lauroyl-sn-glycerol Chemical compound CCCCCCCCCCCC(=O)OC[C@@H](O)CO ARIWANIATODDMH-AWEZNQCLSA-N 0.000 claims description 7
- ARIWANIATODDMH-UHFFFAOYSA-N Lauric acid monoglyceride Natural products CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 claims description 7
- BAECOWNUKCLBPZ-HIUWNOOHSA-N Triolein Natural products O([C@H](OCC(=O)CCCCCCC/C=C\CCCCCCCC)COC(=O)CCCCCCC/C=C\CCCCCCCC)C(=O)CCCCCCC/C=C\CCCCCCCC BAECOWNUKCLBPZ-HIUWNOOHSA-N 0.000 claims description 7
- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 claims description 7
- 150000001841 cholesterols Chemical class 0.000 claims description 7
- VUFOSBDICLTFMS-UHFFFAOYSA-M ethyl-hexadecyl-dimethylazanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)CC VUFOSBDICLTFMS-UHFFFAOYSA-M 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 claims description 7
- QAQSNXHKHKONNS-UHFFFAOYSA-N 1-ethyl-2-hydroxy-4-methyl-6-oxopyridine-3-carboxamide Chemical compound CCN1C(O)=C(C(N)=O)C(C)=CC1=O QAQSNXHKHKONNS-UHFFFAOYSA-N 0.000 claims description 6
- OQQOAWVKVDAJOI-UHFFFAOYSA-N (2-dodecanoyloxy-3-hydroxypropyl) dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCCCCC OQQOAWVKVDAJOI-UHFFFAOYSA-N 0.000 claims description 5
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 5
- 235000019485 Safflower oil Nutrition 0.000 claims description 5
- 235000019486 Sunflower oil Nutrition 0.000 claims description 5
- 239000008163 avocado oil Substances 0.000 claims description 5
- 235000021302 avocado oil Nutrition 0.000 claims description 5
- 239000000828 canola oil Substances 0.000 claims description 5
- 235000019519 canola oil Nutrition 0.000 claims description 5
- 235000005687 corn oil Nutrition 0.000 claims description 5
- 239000002285 corn oil Substances 0.000 claims description 5
- 229940013317 fish oils Drugs 0.000 claims description 5
- 229960000890 hydrocortisone Drugs 0.000 claims description 5
- 239000004006 olive oil Substances 0.000 claims description 5
- 235000008390 olive oil Nutrition 0.000 claims description 5
- 235000005713 safflower oil Nutrition 0.000 claims description 5
- 239000003813 safflower oil Substances 0.000 claims description 5
- 239000008159 sesame oil Substances 0.000 claims description 5
- 235000011803 sesame oil Nutrition 0.000 claims description 5
- 229940038774 squalene oil Drugs 0.000 claims description 5
- 239000002600 sunflower oil Substances 0.000 claims description 5
- 239000011782 vitamin Substances 0.000 claims description 5
- 229940088594 vitamin Drugs 0.000 claims description 5
- 229930003231 vitamin Natural products 0.000 claims description 5
- 235000013343 vitamin Nutrition 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 239000000693 micelle Substances 0.000 claims description 4
- 230000000415 inactivating effect Effects 0.000 claims description 3
- CXRFDZFCGOPDTD-UHFFFAOYSA-M Cetrimide Chemical compound [Br-].CCCCCCCCCCCCCC[N+](C)(C)C CXRFDZFCGOPDTD-UHFFFAOYSA-M 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims description 2
- SXPWTBGAZSPLHA-UHFFFAOYSA-M cetalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SXPWTBGAZSPLHA-UHFFFAOYSA-M 0.000 claims description 2
- 229960000228 cetalkonium chloride Drugs 0.000 claims description 2
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 claims description 2
- XJWSAJYUBXQQDR-UHFFFAOYSA-M dodecyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)C XJWSAJYUBXQQDR-UHFFFAOYSA-M 0.000 claims description 2
- 239000001525 mentha piperita l. herb oil Substances 0.000 claims description 2
- 235000019477 peppermint oil Nutrition 0.000 claims description 2
- RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 239000000796 flavoring agent Substances 0.000 claims 2
- 235000019634 flavors Nutrition 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 206010019375 Helicobacter infections Diseases 0.000 abstract 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 13
- 239000003995 emulsifying agent Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 244000068988 Glycine max Species 0.000 description 10
- 235000010469 Glycine max Nutrition 0.000 description 10
- 239000000126 substance Substances 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 7
- 208000015181 infectious disease Diseases 0.000 description 6
- 210000004379 membrane Anatomy 0.000 description 6
- 239000012528 membrane Substances 0.000 description 6
- PSLWZOIUBRXAQW-UHFFFAOYSA-M dimethyl(dioctadecyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC PSLWZOIUBRXAQW-UHFFFAOYSA-M 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 238000004220 aggregation Methods 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 4
- 239000002199 base oil Substances 0.000 description 4
- 229960000686 benzalkonium chloride Drugs 0.000 description 4
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 239000006071 cream Substances 0.000 description 4
- 208000007882 Gastritis Diseases 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 208000008469 Peptic Ulcer Diseases 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 150000002314 glycerols Chemical class 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 230000003641 microbiacidal effect Effects 0.000 description 3
- 210000003097 mucus Anatomy 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 208000011906 peptic ulcer disease Diseases 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 206010017964 Gastrointestinal infection Diseases 0.000 description 2
- 241000193990 Streptococcus sp. 'group B' Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 150000001449 anionic compounds Chemical class 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 244000052616 bacterial pathogen Species 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- OGQYPPBGSLZBEG-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC OGQYPPBGSLZBEG-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 230000002779 inactivation Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002324 mouth wash Substances 0.000 description 2
- 229940051866 mouthwash Drugs 0.000 description 2
- 210000004400 mucous membrane Anatomy 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 125000002467 phosphate group Chemical class [H]OP(=O)(O[H])O[*] 0.000 description 2
- 229940068065 phytosterols Drugs 0.000 description 2
- 210000002345 respiratory system Anatomy 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000007910 systemic administration Methods 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 208000035143 Bacterial infection Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 238000009631 Broth culture Methods 0.000 description 1
- 241000186427 Cutibacterium acnes Species 0.000 description 1
- 241000207201 Gardnerella vaginalis Species 0.000 description 1
- 241000606768 Haemophilus influenzae Species 0.000 description 1
- 241000589989 Helicobacter Species 0.000 description 1
- 239000000232 Lipid Bilayer Substances 0.000 description 1
- 241000588652 Neisseria gonorrhoeae Species 0.000 description 1
- 241000588650 Neisseria meningitidis Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000191963 Staphylococcus epidermidis Species 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- 108010046334 Urease Proteins 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 239000006161 blood agar Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 210000003027 ear inner Anatomy 0.000 description 1
- 206010017758 gastric cancer Diseases 0.000 description 1
- 208000010749 gastric carcinoma Diseases 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 208000015589 gastric non-hodgkin lymphoma Diseases 0.000 description 1
- 229940047650 haemophilus influenzae Drugs 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000008206 lipophilic material Substances 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 229940113124 polysorbate 60 Drugs 0.000 description 1
- 229940055019 propionibacterium acne Drugs 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 201000000498 stomach carcinoma Diseases 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/14—Quaternary ammonium compounds, e.g. edrophonium, choline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
- A61K31/231—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms having one or two double bonds
-
- 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
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Liposomes
- A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers
- A61K9/1272—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers with substantial amounts of non-phosphatidyl, i.e. non-acylglycerophosphate, surfactants as bilayer-forming substances, e.g. cationic lipids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- 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
-
- 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
-
- 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
- A61P31/10—Antimycotics
-
- 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
- A61P31/12—Antivirals
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Emergency Medicine (AREA)
- Dispersion Chemistry (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Dermatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Virology (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Colloid Chemistry (AREA)
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002190604A CA2190604A1 (en) | 1994-05-20 | 1995-05-18 | Antibacterial oil-in-water emulsions |
EP95920505A EP0765151B1 (en) | 1994-05-20 | 1995-05-18 | Antibacterial oil-in-water emulsions |
BR9507669A BR9507669A (en) | 1994-05-20 | 1995-05-18 | Antibacterial oil-in-water emulsions |
DE69524953T DE69524953T2 (en) | 1994-05-20 | 1995-05-18 | ANTIBACTERIAL OIL-IN-WATER EMULSION |
AU25936/95A AU2593695A (en) | 1994-05-20 | 1995-05-18 | Antibacterial oil-in-water emulsions |
JP7530417A JPH10500686A (en) | 1994-05-20 | 1995-05-18 | Antibacterial oil-in-water emulsion |
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US08/246,868 US5547677A (en) | 1994-05-20 | 1994-05-20 | Antimicrobial oil-in-water emulsions |
US08/322,827 US5549901A (en) | 1994-05-20 | 1994-10-13 | Antimicrobial oil-in-water emulsions |
US32973094A | 1994-10-26 | 1994-10-26 | |
US08/322,827 | 1994-10-26 | ||
US08/246,868 | 1994-10-26 | ||
US08/329,730 | 1994-10-26 |
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WO1995031956A1 true WO1995031956A1 (en) | 1995-11-30 |
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PCT/US1995/006236 WO1995031966A1 (en) | 1994-05-20 | 1995-05-18 | Antimicrobial oil-in-water emulsions |
PCT/US1995/006234 WO1995031956A1 (en) | 1994-05-20 | 1995-05-18 | Antibacterial oil-in-water emulsions |
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PCT/US1995/006236 WO1995031966A1 (en) | 1994-05-20 | 1995-05-18 | Antimicrobial oil-in-water emulsions |
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US (1) | US5618840A (en) |
EP (2) | EP0765151B1 (en) |
JP (2) | JPH10500686A (en) |
CN (2) | CN1159158A (en) |
AU (2) | AU2593695A (en) |
BR (2) | BR9507742A (en) |
CA (2) | CA2190604A1 (en) |
DE (2) | DE69524953T2 (en) |
ES (1) | ES2180636T3 (en) |
WO (2) | WO1995031966A1 (en) |
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WO1997019593A1 (en) * | 1995-11-28 | 1997-06-05 | Wider Michael D | Antimicrobial composition and methods of use therefor |
WO1997025032A2 (en) * | 1996-01-05 | 1997-07-17 | Ambi Inc. | Monoglyceride compositions and their use against helicobacter |
WO1997025032A3 (en) * | 1996-01-05 | 1997-11-13 | Applied Microbiology Inc | Monoglyceride compositions and their use against helicobacter |
US5908862A (en) * | 1996-07-31 | 1999-06-01 | Abbot Laboratories | Water-miscible esters of mono--and diglycerides having antibacterial activity and their use in inhibiting infection |
US5912372A (en) * | 1996-07-31 | 1999-06-15 | Abbott Laboratories | Water-miscible esters of monoglycerides having antimicrobial activity |
US5958974A (en) * | 1996-07-31 | 1999-09-28 | Abbott Laboratories | Nutritional formulations containing water-miscible lipid derivatives as antibacterial agents |
US5981587A (en) * | 1996-07-31 | 1999-11-09 | Abbott Laboratories | Water-miscible esters of mono- and diglycerides having antimicrobial activity and their use in inhibiting infection |
US6066669A (en) * | 1996-07-31 | 2000-05-23 | Abbott Laboratories | Nutritional formulations containing water-miscible lipid derivatives as anti-bacterial agents |
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Also Published As
Publication number | Publication date |
---|---|
WO1995031966A1 (en) | 1995-11-30 |
DE69527624T2 (en) | 2003-04-03 |
DE69524953D1 (en) | 2002-02-14 |
EP0765151B1 (en) | 2002-01-09 |
CN1159158A (en) | 1997-09-10 |
US5618840A (en) | 1997-04-08 |
EP0760650A1 (en) | 1997-03-12 |
EP0765151A4 (en) | 1998-11-25 |
JPH10500687A (en) | 1998-01-20 |
EP0760650A4 (en) | 1998-11-25 |
DE69527624D1 (en) | 2002-09-05 |
AU687562B2 (en) | 1998-02-26 |
CA2190606A1 (en) | 1995-11-30 |
AU2593695A (en) | 1995-12-18 |
EP0765151A1 (en) | 1997-04-02 |
EP0760650B1 (en) | 2002-07-31 |
BR9507742A (en) | 1997-10-07 |
CN1156404A (en) | 1997-08-06 |
ES2180636T3 (en) | 2003-02-16 |
CA2190604A1 (en) | 1995-11-30 |
CN1158069C (en) | 2004-07-21 |
BR9507669A (en) | 1997-10-07 |
JPH10500686A (en) | 1998-01-20 |
AU2593795A (en) | 1995-12-18 |
DE69524953T2 (en) | 2002-08-29 |
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