HU177081B - Process for preparing the occlusion complex of allicin with cyclodextrin - Google Patents
Process for preparing the occlusion complex of allicin with cyclodextrin Download PDFInfo
- Publication number
- HU177081B HU177081B HU78CI1871A HUCI001871A HU177081B HU 177081 B HU177081 B HU 177081B HU 78CI1871 A HU78CI1871 A HU 78CI1871A HU CI001871 A HUCI001871 A HU CI001871A HU 177081 B HU177081 B HU 177081B
- Authority
- HU
- Hungary
- Prior art keywords
- allicin
- cyclodextrin
- complex
- solution
- inclusion complex
- Prior art date
Links
- JDLKFOPOAOFWQN-VIFPVBQESA-N Allicin Natural products C=CCS[S@](=O)CC=C JDLKFOPOAOFWQN-VIFPVBQESA-N 0.000 title claims abstract description 66
- JDLKFOPOAOFWQN-UHFFFAOYSA-N allicin Chemical compound C=CCSS(=O)CC=C JDLKFOPOAOFWQN-UHFFFAOYSA-N 0.000 title claims abstract description 66
- 235000010081 allicin Nutrition 0.000 title claims abstract description 66
- 229920000858 Cyclodextrin Polymers 0.000 title claims abstract description 41
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 239000000243 solution Substances 0.000 claims abstract description 11
- 239000007864 aqueous solution Substances 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 4
- 230000000845 anti-microbial effect Effects 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 15
- 239000001116 FEMA 4028 Substances 0.000 claims description 14
- 229960004853 betadex Drugs 0.000 claims description 14
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims description 13
- 235000011175 beta-cyclodextrine Nutrition 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 230000000843 anti-fungal effect Effects 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 230000000844 anti-bacterial effect Effects 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 claims description 3
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 claims description 3
- 229940043377 alpha-cyclodextrin Drugs 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 230000002906 microbiologic effect Effects 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 241000233866 Fungi Species 0.000 claims 4
- 230000005764 inhibitory process Effects 0.000 claims 3
- 244000005700 microbiome Species 0.000 claims 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 241000222122 Candida albicans Species 0.000 claims 1
- 206010017533 Fungal infection Diseases 0.000 claims 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims 1
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000001580 bacterial effect Effects 0.000 claims 1
- 229940095731 candida albicans Drugs 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 239000008298 dragée Substances 0.000 claims 1
- 238000011156 evaluation Methods 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 208000024386 fungal infectious disease Diseases 0.000 claims 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims 1
- 229920000053 polysorbate 80 Polymers 0.000 claims 1
- 230000005180 public health Effects 0.000 claims 1
- 230000000717 retained effect Effects 0.000 claims 1
- 239000007921 spray Substances 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
- 230000001408 fungistatic effect Effects 0.000 abstract description 2
- PFRGXCVKLLPLIP-UHFFFAOYSA-N diallyl disulfide Chemical compound C=CCSSCC=C PFRGXCVKLLPLIP-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 240000002234 Allium sativum Species 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 235000004611 garlic Nutrition 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- FCSSPCOFDUKHPV-UHFFFAOYSA-N 2-Propenyl propyl disulfide Chemical compound CCCSSCC=C FCSSPCOFDUKHPV-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- CBQYNPHHHJTCJS-UHFFFAOYSA-N Alline Chemical compound C1=CC=C2C3(O)CCN(C)C3NC2=C1 CBQYNPHHHJTCJS-UHFFFAOYSA-N 0.000 description 2
- RMKCQUWJDRTEHE-UHFFFAOYSA-N Diallyltetrasulfane Chemical compound C=CCSSSSCC=C RMKCQUWJDRTEHE-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- XUHLIQGRKRUKPH-UHFFFAOYSA-N S-allyl-L-cysteine sulfoxide Natural products OC(=O)C(N)CS(=O)CC=C XUHLIQGRKRUKPH-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- NAXKFVIRJICPAO-LHNWDKRHSA-N [(1R,3S,4R,6R,7R,9S,10S,12R,13S,15S,16R,18S,19S,21S,22S,24S,25S,27S,28R,30R,31R,33S,34S,36R,37R,39R,40S,42R,44R,46S,48S,50R,52S,54S,56S)-46,48,50,52,54,56-hexakis(hydroxymethyl)-2,8,14,20,26,32,38,43,45,47,49,51,53,55-tetradecaoxa-5,11,17,23,29,35,41-heptathiapentadecacyclo[37.3.2.23,7.29,13.215,19.221,25.227,31.233,37.04,6.010,12.016,18.022,24.028,30.034,36.040,42]hexapentacontan-44-yl]methanol Chemical compound OC[C@H]1O[C@H]2O[C@H]3[C@H](CO)O[C@H](O[C@H]4[C@H](CO)O[C@H](O[C@@H]5[C@@H](CO)O[C@H](O[C@H]6[C@H](CO)O[C@H](O[C@H]7[C@H](CO)O[C@@H](O[C@H]8[C@H](CO)O[C@@H](O[C@@H]1[C@@H]1S[C@@H]21)[C@@H]1S[C@H]81)[C@H]1S[C@@H]71)[C@H]1S[C@H]61)[C@H]1S[C@@H]51)[C@H]1S[C@@H]41)[C@H]1S[C@H]31 NAXKFVIRJICPAO-LHNWDKRHSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229940097362 cyclodextrins Drugs 0.000 description 2
- UBAXRAHSPKWNCX-UHFFFAOYSA-N diallyl trisulfide Chemical compound C=CCSSSCC=C UBAXRAHSPKWNCX-UHFFFAOYSA-N 0.000 description 2
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 2
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000000634 powder X-ray diffraction Methods 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 239000001754 3-prop-2-enyldisulfanyldisulfanylprop-1-ene Substances 0.000 description 1
- XUHLIQGRKRUKPH-GCXOYZPQSA-N Alliin Natural products N[C@H](C[S@@](=O)CC=C)C(O)=O XUHLIQGRKRUKPH-GCXOYZPQSA-N 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 241001337994 Cryptococcus <scale insect> Species 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241001480035 Epidermophyton Species 0.000 description 1
- 208000007530 Essential hypertension Diseases 0.000 description 1
- 206010056663 Gastric infection Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical group OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 206010022678 Intestinal infections Diseases 0.000 description 1
- 241001480037 Microsporum Species 0.000 description 1
- 241000244206 Nematoda Species 0.000 description 1
- OZBZONOEYUBXTD-UHFFFAOYSA-N OOOOOOOOO Chemical compound OOOOOOOOO OZBZONOEYUBXTD-UHFFFAOYSA-N 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000000184 acid digestion Methods 0.000 description 1
- XUHLIQGRKRUKPH-DYEAUMGKSA-N alliin Chemical compound OC(=O)[C@@H](N)C[S@@](=O)CC=C XUHLIQGRKRUKPH-DYEAUMGKSA-N 0.000 description 1
- 235000015295 alliin Nutrition 0.000 description 1
- -1 allyl ester Chemical class 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229940124600 folk medicine Drugs 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000010647 garlic oil Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 239000013080 microcrystalline material Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000004810 partition chromatography Methods 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- CBXWGGFGZDVPNV-UHFFFAOYSA-N so4-so4 Chemical compound OS(O)(=O)=O.OS(O)(=O)=O CBXWGGFGZDVPNV-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
-
- 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
- A61K31/255—Esters, e.g. nitroglycerine, selenocyanates of sulfoxy acids or sulfur analogues thereof
-
- 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
- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
- A61K47/6951—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
- C08B37/0015—Inclusion compounds, i.e. host-guest compounds, e.g. polyrotaxanes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Nanotechnology (AREA)
- Molecular Biology (AREA)
- Materials Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Emergency Medicine (AREA)
- Biophysics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Medical Informatics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Communicable Diseases (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU78CI1871A HU177081B (en) | 1978-12-12 | 1978-12-12 | Process for preparing the occlusion complex of allicin with cyclodextrin |
| DE19792948869 DE2948869A1 (de) | 1978-12-12 | 1979-12-05 | Die mit cyclodextrin gebildeten einschlusskomplexe des allycins sowie verfahren zur herstellung dieser komplexe und diese enthaltende arzneimittelpraeparate |
| YU02990/79A YU299079A (en) | 1978-12-12 | 1979-12-10 | Process for obtaining an inclusion complec of allicin with cyclodextrines |
| FR7930212A FR2444060A1 (fr) | 1978-12-12 | 1979-12-10 | Complexes d'inclusion d'allycine avec les cyclodextrines, leur preparation et les compositions pharmaceutiques qui les contiennent |
| SU792854753A SU938732A3 (ru) | 1978-12-12 | 1979-12-11 | Способ получени комплекса аллицин-циклодекстрин |
| CH1097979A CH642347A5 (de) | 1978-12-12 | 1979-12-11 | Die mit cyclodextrin gebildeten einschlusskomplexe des allycins sowie verfahren zur herstellung dieser komplexe und diese enthaltende arzneimittelpraeparate. |
| DK526779A DK526779A (da) | 1978-12-12 | 1979-12-11 | Inklusionskompleks af allycin med et cyclodextrin dets fremstilling og anvendelse |
| NO794044A NO794044L (no) | 1978-12-12 | 1979-12-11 | Fremgangsmaate ved fremstilling av inklusjonskomplekser av allycin med cyclodextriner |
| GB7942695A GB2061987B (en) | 1978-12-12 | 1979-12-11 | Cyclodextrin complexes their preparation and pharmaceutical compositions containing them |
| AT0782979A AT363492B (de) | 1978-12-12 | 1979-12-12 | Verfahren zur herstellung von cyclodextrin-einschlusskomplexen des allicins |
| JP16140379A JPS55115866A (en) | 1978-12-12 | 1979-12-12 | Allicinncyclodextrin contained complex and medicine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU78CI1871A HU177081B (en) | 1978-12-12 | 1978-12-12 | Process for preparing the occlusion complex of allicin with cyclodextrin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU177081B true HU177081B (en) | 1981-07-28 |
Family
ID=10994715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU78CI1871A HU177081B (en) | 1978-12-12 | 1978-12-12 | Process for preparing the occlusion complex of allicin with cyclodextrin |
Country Status (11)
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU184066B (en) | 1979-12-28 | 1984-06-28 | Chinoin Gyogyszer Es Vegyeszet | Plant growth regulating substance and process for preparing such compound |
| HU181733B (en) | 1980-08-07 | 1983-11-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing sorbents containing cyclodextrin on cellulose base |
| JPS5920230A (ja) * | 1982-07-19 | 1984-02-01 | チバ−ガイギ−・アクチエンゲゼルシヤフト | ピルプロフエン含有薬剤 |
| FR2550193A1 (fr) * | 1983-08-05 | 1985-02-08 | Sal Fine Chemicals Internation | Complexes d'inclusion de trisulfure de methyle et d'allyle avec des cyclodextrines, leur procede de preparation et compositions pharmaceutiques les contenant |
| HU196230B (en) * | 1983-12-29 | 1988-10-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing water-soluble forms of polyene antibiotics and pharmaceutics comprising such active ingredient and plant protective with antifungal effect |
| US4678598A (en) * | 1985-08-06 | 1987-07-07 | Kao Corporation | Liquid shampoo composition |
| DE3638290A1 (de) * | 1986-11-07 | 1988-05-19 | Herbe Wirkstoffe Gmbh | Arzneimittelzubereitung |
| US4774329A (en) * | 1987-08-04 | 1988-09-27 | American Maize-Products Company | Controlled release agent for cetylpyridinium chloride |
| ATE124422T1 (de) * | 1989-04-12 | 1995-07-15 | Procter & Gamble | Festes verbraucherprodukt, welches feinteilige cyclodextrin-komplexe enthält. |
| SE8902235D0 (sv) * | 1989-06-20 | 1989-06-20 | Haessle Ab | Novel cyclodextrin inclusion complexes |
| CA2013485C (en) * | 1990-03-06 | 1997-04-22 | John Michael Gardlik | Solid consumer product compositions containing small particle cyclodextrin complexes |
| DE4024155C2 (de) * | 1990-07-30 | 1995-12-07 | Marcela Dipl Ing Holzhey | Verwendung eines "Allicin-Urotropin" Produktes für den Bereich der inneren Behandlung (oral, Injektionen und Dauertropfinfusionen) von Menschen und Tieren bei Pilzerkrankungen |
| DE4338508A1 (de) * | 1993-11-11 | 1995-05-18 | Asta Medica Ag | Arzneimittelzubereitungen enthaltend Thioctsäure oder Dihydroliponsäure in Form von Einschlußverbindungen mit Cyclodextrinen oder Cyclodextrinderivaten und in Form von Granulaten, Kau- oder Brausetabletten |
| DE19500863A1 (de) * | 1995-01-13 | 1996-07-18 | Consortium Elektrochem Ind | Verfahren zur Herstellung von Ajoen |
| GB0120887D0 (en) * | 2001-08-29 | 2001-10-17 | Sahajanand Biotech Private Ltd | Local drug delivery system in coronary stents |
| GB0122793D0 (en) * | 2001-09-21 | 2001-11-14 | Stone Island Holdings Ltd | Allicin |
| EP1721534A1 (en) * | 2004-03-03 | 2006-11-15 | Mousala, S. L. | Use of extracts and compounds of allium-genus plants as preservatives in the food and agri-food industries |
| GB0422582D0 (en) * | 2004-10-11 | 2004-11-10 | Nasaleze Patents Ltd | Pharmaceutical compositions |
| CN107802842B (zh) * | 2016-09-07 | 2022-04-12 | 汤臣倍健股份有限公司 | 大蒜素矫味制剂及其制备方法 |
| CN107789345B (zh) * | 2016-09-07 | 2022-06-28 | 汤臣倍健股份有限公司 | 矫味大蒜素-环糊精复合物及其制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3061444A (en) * | 1960-10-07 | 1962-10-30 | Gen Foods Corp | Inclusion compounds incorporating edible juice constituents |
| HU174699B (hu) * | 1977-07-01 | 1980-03-28 | Chinoin Gyogyszer Es Vegyeszet | Sposob poluchenija natural'nykh i sinteticheskikh ciklodektrinnykh okkluzionnykh kompleksov prjaznostej, aromatov i vkusnykh vehhestv |
-
1978
- 1978-12-12 HU HU78CI1871A patent/HU177081B/hu unknown
-
1979
- 1979-12-05 DE DE19792948869 patent/DE2948869A1/de active Granted
- 1979-12-10 FR FR7930212A patent/FR2444060A1/fr active Granted
- 1979-12-10 YU YU02990/79A patent/YU299079A/xx unknown
- 1979-12-11 DK DK526779A patent/DK526779A/da not_active Application Discontinuation
- 1979-12-11 CH CH1097979A patent/CH642347A5/de not_active IP Right Cessation
- 1979-12-11 SU SU792854753A patent/SU938732A3/ru active
- 1979-12-11 GB GB7942695A patent/GB2061987B/en not_active Expired
- 1979-12-11 NO NO794044A patent/NO794044L/no unknown
- 1979-12-12 AT AT0782979A patent/AT363492B/de not_active IP Right Cessation
- 1979-12-12 JP JP16140379A patent/JPS55115866A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB2061987A (en) | 1981-05-20 |
| YU299079A (en) | 1983-06-30 |
| SU938732A3 (ru) | 1982-06-23 |
| ATA782979A (de) | 1981-01-15 |
| CH642347A5 (de) | 1984-04-13 |
| GB2061987B (en) | 1983-05-18 |
| NO794044L (no) | 1980-06-13 |
| FR2444060A1 (fr) | 1980-07-11 |
| JPS55115866A (en) | 1980-09-06 |
| DE2948869C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-07-09 |
| AT363492B (de) | 1981-08-10 |
| JPS642105B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-01-13 |
| FR2444060B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-06-29 |
| DE2948869A1 (de) | 1980-07-03 |
| DK526779A (da) | 1980-06-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 |