US3893995A - Method for obtaining polyfructosans - Google Patents
Method for obtaining polyfructosans Download PDFInfo
- Publication number
- US3893995A US3893995A US205293A US20529371A US3893995A US 3893995 A US3893995 A US 3893995A US 205293 A US205293 A US 205293A US 20529371 A US20529371 A US 20529371A US 3893995 A US3893995 A US 3893995A
- Authority
- US
- United States
- Prior art keywords
- polyfructosan
- extract
- low alcohol
- water
- filtering
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229920000377 Sinistrin Polymers 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title claims description 17
- 210000000056 organ Anatomy 0.000 claims abstract description 6
- 241000209510 Liliopsida Species 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 239000000284 extract Substances 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
- 239000006188 syrup Substances 0.000 claims description 12
- 235000020357 syrup Nutrition 0.000 claims description 12
- 239000002244 precipitate Substances 0.000 claims description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 239000000920 calcium hydroxide Substances 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 6
- 238000001556 precipitation Methods 0.000 claims description 6
- 238000005342 ion exchange Methods 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 4
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 238000004898 kneading Methods 0.000 claims description 4
- 238000011033 desalting Methods 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 230000001376 precipitating effect Effects 0.000 claims 1
- 229940039227 diagnostic agent Drugs 0.000 abstract description 6
- 239000000032 diagnostic agent Substances 0.000 abstract description 6
- 238000003860 storage Methods 0.000 abstract description 5
- 230000003907 kidney function Effects 0.000 abstract description 4
- 239000000243 solution Substances 0.000 description 13
- 239000000126 substance Substances 0.000 description 9
- 229920001202 Inulin Polymers 0.000 description 8
- JYJIGFIDKWBXDU-MNNPPOADSA-N inulin Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@]1(OC[C@]2(OC[C@]3(OC[C@]4(OC[C@]5(OC[C@]6(OC[C@]7(OC[C@]8(OC[C@]9(OC[C@]%10(OC[C@]%11(OC[C@]%12(OC[C@]%13(OC[C@]%14(OC[C@]%15(OC[C@]%16(OC[C@]%17(OC[C@]%18(OC[C@]%19(OC[C@]%20(OC[C@]%21(OC[C@]%22(OC[C@]%23(OC[C@]%24(OC[C@]%25(OC[C@]%26(OC[C@]%27(OC[C@]%28(OC[C@]%29(OC[C@]%30(OC[C@]%31(OC[C@]%32(OC[C@]%33(OC[C@]%34(OC[C@]%35(OC[C@]%36(O[C@@H]%37[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O%37)O)[C@H]([C@H](O)[C@@H](CO)O%36)O)[C@H]([C@H](O)[C@@H](CO)O%35)O)[C@H]([C@H](O)[C@@H](CO)O%34)O)[C@H]([C@H](O)[C@@H](CO)O%33)O)[C@H]([C@H](O)[C@@H](CO)O%32)O)[C@H]([C@H](O)[C@@H](CO)O%31)O)[C@H]([C@H](O)[C@@H](CO)O%30)O)[C@H]([C@H](O)[C@@H](CO)O%29)O)[C@H]([C@H](O)[C@@H](CO)O%28)O)[C@H]([C@H](O)[C@@H](CO)O%27)O)[C@H]([C@H](O)[C@@H](CO)O%26)O)[C@H]([C@H](O)[C@@H](CO)O%25)O)[C@H]([C@H](O)[C@@H](CO)O%24)O)[C@H]([C@H](O)[C@@H](CO)O%23)O)[C@H]([C@H](O)[C@@H](CO)O%22)O)[C@H]([C@H](O)[C@@H](CO)O%21)O)[C@H]([C@H](O)[C@@H](CO)O%20)O)[C@H]([C@H](O)[C@@H](CO)O%19)O)[C@H]([C@H](O)[C@@H](CO)O%18)O)[C@H]([C@H](O)[C@@H](CO)O%17)O)[C@H]([C@H](O)[C@@H](CO)O%16)O)[C@H]([C@H](O)[C@@H](CO)O%15)O)[C@H]([C@H](O)[C@@H](CO)O%14)O)[C@H]([C@H](O)[C@@H](CO)O%13)O)[C@H]([C@H](O)[C@@H](CO)O%12)O)[C@H]([C@H](O)[C@@H](CO)O%11)O)[C@H]([C@H](O)[C@@H](CO)O%10)O)[C@H]([C@H](O)[C@@H](CO)O9)O)[C@H]([C@H](O)[C@@H](CO)O8)O)[C@H]([C@H](O)[C@@H](CO)O7)O)[C@H]([C@H](O)[C@@H](CO)O6)O)[C@H]([C@H](O)[C@@H](CO)O5)O)[C@H]([C@H](O)[C@@H](CO)O4)O)[C@H]([C@H](O)[C@@H](CO)O3)O)[C@H]([C@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 JYJIGFIDKWBXDU-MNNPPOADSA-N 0.000 description 8
- 229940029339 inulin Drugs 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 235000011116 calcium hydroxide Nutrition 0.000 description 5
- 210000003734 kidney Anatomy 0.000 description 5
- VYSWEVWBWJBBHH-UHFFFAOYSA-N 2-[5-[[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxymethyl]-2-[[2-[[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxyoxolan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound OCC1OC(OC2(COC3(COC4(CO)OC(CO)C(O)C4O)OC(CO)C(O)C3O)OC(COC5(CO)OC(CO)C(O)C5O)C(O)C2O)C(O)C(O)C1O VYSWEVWBWJBBHH-UHFFFAOYSA-N 0.000 description 4
- 240000002234 Allium sativum Species 0.000 description 4
- 244000304921 Charybdis maritima Species 0.000 description 4
- 235000004611 garlic Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 241000234282 Allium Species 0.000 description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 2
- 239000005715 Fructose Substances 0.000 description 2
- 229930091371 Fructose Natural products 0.000 description 2
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 2
- 241000209504 Poaceae Species 0.000 description 2
- GHNYBHXFHIPTEK-UHFFFAOYSA-N Urginea maritima Natural products CC1OC(OC2C(O)C(O)C(OC3CCC4(C)C(C3)C(CC5(O)C4CCC6(C)C(CCC56O)C7=COC(=O)C=C7)OC(=O)C)OC2CO)C(O)C(O)C1O GHNYBHXFHIPTEK-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 150000002772 monosaccharides Chemical group 0.000 description 2
- 239000004069 plant analysis Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- LSMIOFMZNVEEBR-ICLSSMQGSA-N scilliroside Chemical compound C=1([C@@H]2[C@@]3(C)CC[C@H]4[C@@]([C@]3(CC2)O)(O)C[C@H](C2=C[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)CC[C@@]24C)OC(=O)C)C=CC(=O)OC=1 LSMIOFMZNVEEBR-ICLSSMQGSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- 244000298479 Cichorium intybus Species 0.000 description 1
- 235000007542 Cichorium intybus Nutrition 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 206010013786 Dry skin Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 229930187199 Graminin Natural products 0.000 description 1
- 240000008892 Helianthus tuberosus Species 0.000 description 1
- 235000003230 Helianthus tuberosus Nutrition 0.000 description 1
- 244000116484 Inula helenium Species 0.000 description 1
- 235000002598 Inula helenium Nutrition 0.000 description 1
- 241000234280 Liliaceae Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical class [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- 229910001864 baryta Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000037336 dry skin Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- BJHIKXHVCXFQLS-UYFOZJQFSA-N fructose group Chemical group OCC(=O)[C@@H](O)[C@H](O)[C@H](O)CO BJHIKXHVCXFQLS-UYFOZJQFSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 238000005325 percolation Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C08B37/0051—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Fructofuranans, e.g. beta-2,6-D-fructofuranan, i.e. levan; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/88—Liliopsida (monocotyledons)
- A61K36/896—Liliaceae (Lily family), e.g. daylily, plantain lily, Hyacinth or narcissus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/88—Liliopsida (monocotyledons)
- A61K36/896—Liliaceae (Lily family), e.g. daylily, plantain lily, Hyacinth or narcissus
- A61K36/8962—Allium, e.g. garden onion, leek, garlic or chives
Definitions
- ABSTRACT A kidney function diagnostic agent comprising high water-soluble polyfructosans derived from the storage organs of monocotyledon plants.
- inulin For this purpose, a known volume of inulin solution is administered parenterally and the elimination of the inulin is followed up with a periodic concentration determination in the blood and the urine.
- the prerequisite for this use is the property of inulin to be neither stored, nor chemically altered in the body.
- inulin has so far proved to be excellent for this task as a standard substance.
- the chief disadvantage in the use of inulin resides in the fact that it is difficult to dissolve in cold water.
- the normally employed percent solution crystallizes at cold temperatures, and is accompanied by the formation of a crusty precipitate. Before it can be given to a patient, this precipitate must once again be dissolved through heat.
- kidney diagnostic agents themselves longknown, comprising the watersoluble polyfructosans from the storage organs of certain monocotyledon plants, and especially, from the families of the Liliaceae and the Gramineae.
- the object of this invention is to provide a kidney function diagnostic agent with a polyfructosan content, which is characterized by the fact that it contains water-soluble polyfructosans easily soluble in water from the storage organs of monocotyledon plants, and especially from the families of the Lilicaeae and Gramineae.
- a further object of this invention is to provide a method for the production of polyfructosans for use as a kidney function diagnostic agent, which comprises extracting the particular drugs with low alcohols or with acetone having a water content of -40 percent.
- the extract is preferably brought to a pH of 9 with calcium hydroxide, filtered, and concentrated under reduced pressure, into a thick syrup, whereupon the thickened extract, after addition of about half its weight in a low alcohol (preferably methanol) is aciditied with a strong acid (preferably hydrochloric acid) to a pH of between 1 and 3.
- the polyfructosan is then precipitated with a 2 to 8 fold weight of a low alcohol (preferably methanol) or with acetone, and the precipitate thus obtained is converted into a powdery crystalline form through repeated kneading with a water-free precipitation agent.
- a low alcohol preferably methanol
- acetone preferably acetone
- the solution of the polyfructosan thus obtained can be completely desalted via ion-exchange, treated with active carbon (active charcoal), filtered, and then either filled, after removal of the organic solvent residues by means of distillation, directly into ampoules, or optionally it can be dried, after concentration into a syrup consistency, in a vacuum, to a thin layer.
- the coarsely comminuted plant material is repeatedly extracted with aqueous alcohols or acetone (preferably methanol, ethanol, or isopropanol) or with acetone having 80-40 percent water by means of percolation, if necessary, at increased temperatures.
- aqueous alcohols or acetone preferably methanol, ethanol, or isopropanol
- acetone having 80-40 percent water by means of percolation, if necessary, at increased temperatures.
- the function of the organic solvent is (1) to prevent degradation by microorganisms, (2) to suppress the effect of the polyfructosan-decomposing ferments, and (3) to prevent the dissolution of interfering pectin and shiny substances.
- the extracts thus obtained are alkalized to a pH value of 9 with milk of lime (calcium hydroxide), filtered and the resultant filtrate is evaporated in a vacuum to produce a syrup of about 70-80 percent dry substance content.
- the precipitate which consists of a white, viscous mass, is separated from the supernatant liquid and is thoroughly kneaded several times with small portions of solvent, thereby forming a fine-grained crystalline product which finally is liberated from the adhering liquid by centrifuge or suction filter.
- the substance thus obtained is already very pure but, for parenteral application, it must be dissolve again in water and further purified by'means of ion exchange and filtration of the desalted solution with active carbon.
- the solution thus obtained can either be filled directly into ampoules after removal of the solvent residues through distillation and adjustment' of the EXAMPLE 1 Productionof Polyfructosan (Sinistrin) From the Onion Bulbs of the Composite Urginea Maritima 100 Kg of commercially available dried red sea onion were coarsely ground in a knife-mill with a screen insert having a 4-mm perforation diameter, they are premoistened with 200 Kg of a percent watery metha'v nol solution, and percolated, after standing, for 24 hours with the same solvent at room ter'nperaturehav-v ing a runoff speed of about 4 Kg per hour. A total of 300 Kg of extract were obtained.
- the extract was brought to a pH of 9 with a suspension of 250 g of calcium hydroxide in a little water,the precipitate was filtered off, and the liquid was evaporated, in a vacuum, to a thick syrup. About 75 Kg of syrup containing 80 percent of solid substance was obtained. Accompanied by forceful stirring, 30 Kg of methanol wereintroduced into a thin jet and the almost clear solution, was cooled down to 15C. Accompanied by furtherforceful stirring, a cooled off mixture consisting of 3 liters of concentrated hydrochloric acid and 8 Kg of methanol was added. As a result, Sinistrin was precipitated as a viscous, nacreously-brilliant, yellowish-white mass. The solution, which was clear yellow after standing briefly, was poured off as completely as possible. It contained .salts, fructose and low-molecular oligosaccharides.
- the Sinistrin precipitate about 40 Kg, was forcefully kneaded three times with 40 Kg of methanol, each 4 time, in a kneading machine.
- the supernatant methanol was poured off in each case and was combined with the one obtained during the firstprecipitation, whereby the entire mass was converted into a fine-grained cyrstallin'e suspension. This was contrifuged on a centrifuge and the substance isolated (about 35 Kg).was dissolved in 70 Kg of water.
Landscapes
- Health & Medical Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medical Informatics (AREA)
- Botany (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Biotechnology (AREA)
- Alternative & Traditional Medicine (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT1105570A AT304769B (de) | 1970-12-09 | 1970-12-09 | Nierenfunktionsdiagnosticum und Verfahren zu dessen Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3893995A true US3893995A (en) | 1975-07-08 |
Family
ID=3626494
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US205293A Expired - Lifetime US3893995A (en) | 1970-12-09 | 1971-12-06 | Method for obtaining polyfructosans |
Country Status (13)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5561226A (en) * | 1991-01-23 | 1996-10-01 | Laevosan Gesellschaft Mbh | Process for the production of a pyrogen-free fructan which is readily water-soluble |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2834694A (en) * | 1955-10-07 | 1958-05-13 | Hill Robert | Fructose polymers and method of preparation |
-
1970
- 1970-12-09 AT AT1105570A patent/AT304769B/de not_active IP Right Cessation
-
1971
- 1971-11-16 CH CH1673371A patent/CH573751A5/xx not_active IP Right Cessation
- 1971-11-25 DE DE2158467A patent/DE2158467C3/de not_active Expired
- 1971-12-06 US US205293A patent/US3893995A/en not_active Expired - Lifetime
- 1971-12-07 FR FR7143827A patent/FR2117917B1/fr not_active Expired
- 1971-12-07 SE SE7115670A patent/SE419404B/xx unknown
- 1971-12-07 CS CS8506A patent/CS161145B2/cs unknown
- 1971-12-07 SU SU1752557A patent/SU472509A3/ru active
- 1971-12-08 CA CA129,617A patent/CA973173A/en not_active Expired
- 1971-12-08 YU YU03074/71A patent/YU307471A/xx unknown
- 1971-12-08 DK DK600571A patent/DK132928C/da active
- 1971-12-09 GB GB3537473A patent/GB1369850A/en not_active Expired
- 1971-12-09 JP JP9911371A patent/JPS5420568B1/ja active Pending
- 1971-12-09 GB GB5727271A patent/GB1369849A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2834694A (en) * | 1955-10-07 | 1958-05-13 | Hill Robert | Fructose polymers and method of preparation |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5561226A (en) * | 1991-01-23 | 1996-10-01 | Laevosan Gesellschaft Mbh | Process for the production of a pyrogen-free fructan which is readily water-soluble |
Also Published As
| Publication number | Publication date |
|---|---|
| AT304769B (de) | 1973-01-25 |
| FR2117917A1 (enrdf_load_stackoverflow) | 1972-07-28 |
| DE2158467C3 (de) | 1982-04-08 |
| FR2117917B1 (enrdf_load_stackoverflow) | 1975-08-01 |
| CS161145B2 (enrdf_load_stackoverflow) | 1975-05-04 |
| JPS5420568B1 (enrdf_load_stackoverflow) | 1979-07-24 |
| SE419404B (sv) | 1981-08-03 |
| DK132928B (da) | 1976-03-01 |
| DE2158467A1 (de) | 1972-06-15 |
| DE2158467B2 (de) | 1981-04-23 |
| CH573751A5 (enrdf_load_stackoverflow) | 1976-03-31 |
| DK132928C (da) | 1976-07-26 |
| SU472509A3 (ru) | 1975-05-30 |
| CA973173A (en) | 1975-08-19 |
| GB1369849A (en) | 1974-10-09 |
| GB1369850A (en) | 1974-10-09 |
| YU307471A (en) | 1982-06-18 |
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