Purification Or Recovery Patents (Class 536/127)
  • Patent number: 5169840
    Abstract: The present invention is directed to a material and method for the stimulation of the production of cytokines. Several polysaccharides, including polymers of different size of .sym.1-4 linked D-mannuronic acid (poly-M and M-blocks), chitosan and cellulose oxidized in C-6 position C60XY) induce human monocytes to produce the cytokines. Preferably, the molecular weights of poly-M and chitosan are above 50,000 and 20,000 respectively. Pretreatment of the monocytes with IFN-.gamma. increases the cytokine production from monocytes stimulated with all polysaccharides tested. The subject polysaccharides worked in vivo and in vitro.The present invention has therapeutic utility as vaccine adjuvants and components. Therapeutic compositions comprising biologically active quantities of the compositions of the present invention may be employed to potentiate antibody production in response to vaccine antigens. Anti-tumor, anti-bacteriological, anti-fungal and anti-viral effects may be expected.
    Type: Grant
    Filed: March 27, 1991
    Date of Patent: December 8, 1992
    Assignees: Nobipols Forskningsstiftelse, Protan Biopolymer A/S
    Inventors: Marit Otterlei, Terje Espevik, Gudmund Skjak-Brock, Olav Smidsrod
  • Patent number: 5164377
    Abstract: The present invention relates to sulphated glycosamino glycuronan with antithrombotic activity consisting essentially of salts of dermatan sulphate, chondroitin sulphate and heparan sulphate, characterized bya) an average molecular weight between 4000 and 8000 daltons;b) a nitrogen content between 2.4 and 3.0%;c) a sulphur content between 7.5 and 9.5%;d) a sodium content between 9 and 11%;e) a dermatan sulphate content between 5 and 25%;f) a chondroitin sulphate content less than 9%;g) an anti-Xa activity between 11 and 20 .mu./mg; andh) an antithrombin III dependent antithrombin activity of less than 1 .mu./mg.
    Type: Grant
    Filed: October 3, 1990
    Date of Patent: November 17, 1992
    Assignee: Akzo N.V.
    Inventors: Gijsbert W. K. Van Dedem, Francois E. A. Van Hou Denhoven, Dirk G. Meuleman, Huibert C. T. Moelker, Adrianus L. M. Sanders
  • Patent number: 5155018
    Abstract: A process is provided for isolating and purifying biologically active RNA from a biological sources containing RNA, DNA and other cellular materials. The process involves contacting the RNA-containing source with particles comprising siliceous material, such as finely-divided glass, in the presence of a binding solution comprising concentrated, acidified chaotropic salt. Under these conditions, RNA, but not DNA, binds selectively to the siliceous material, and can be separated easily from the other components of the sample. Preferably, the selective binding process is applied to biological cells containing RNA of interest. Intact cells are disrupted by exposing them to a lysing solution comprising, as its main component, concentrated, acidified chaotropic salt. The RNA is then isolated and purified from the lysate using the selective binding process of the invention.
    Type: Grant
    Filed: July 10, 1991
    Date of Patent: October 13, 1992
    Assignee: Hahnemann University
    Inventors: David Gillespie, Kevin K. Cuddy
  • Patent number: 5149799
    Abstract: A method and an apparatus are provided for cooking and spray-drying a starch. In this method, the starch is uniformly and simultaneously atomized and cooked in the presence of an aqueous medium by means of a single atomization step carried out in an apparatus comprising a two-fluid, internal-mix spray-drying nozzle, coupled to a means for drying the cooked, atomized starch. Uniformly pregelatinized, cold-water-swelling starch with desirable textural, visual and organoleptic properties is advantageously provided by this method and apparatus.
    Type: Grant
    Filed: January 26, 1990
    Date of Patent: September 22, 1992
    Assignee: National Starch and Chemical Investment Holding Corporation
    Inventor: Roger W. Rubens
  • Patent number: 5145956
    Abstract: Separation of anionic oligosaccharides on a preparative scale with high resolution can be achieved by anionic exchange chromatography using PEI-derivatized supports.
    Type: Grant
    Filed: December 11, 1991
    Date of Patent: September 8, 1992
    Assignee: Glycomed Incorporated
    Inventors: Lun H. Lam, David Tyrrell
  • Patent number: 5141648
    Abstract: The present invention provides cleavable conjugates whose linkers contain a labile bond that is cleavable under a variety of mild conditions, including weakly acidic. Since the agent may be bonded directly to the linker, cleavage can result in release of native agent. The invention also provides methods for producing cleavable conjugates. Preferred agents include drugs, toxins, biological response modifiers, radiodiagnostic compounds, radiotherapeutic compounds, and derivatives thereof. The targeting molecule employed in the invention may be an intact molecule, a fragment thereof, or a functional equivalent thereof. In a particularly preferred embodiment, the targeting molecule is a monoclonal antibody directed towards a tumor-associated antigen in man. The invention further provides methods for delivering to the cytoplasm of a target cell an agent free of its targeting molecule carrier.
    Type: Grant
    Filed: March 29, 1991
    Date of Patent: August 25, 1992
    Assignee: NeoRx Corporation
    Inventors: Mark D. Hylarides, Ananthachari Srinivasan, Jeffrey N. Fitzner, Vivekananda M. Vrudhula
  • Patent number: 5137878
    Abstract: Ginsenosides Rb.sub.1 and Rg.sub.1 enhance the availability of acetylcholine in the cortical and hippocampal regions of the brain and alleviaate the symptoms of Alzheimer-type senile dementia. The Rb.sub.1 or Rg.sub.1 may be administered together with a metabolic precursor for acetylcholine and/or with a cholinesterase inhibitor.Pure Rb.sub.1 is located from a mixture of ginsenosides by a process involving vacuum chromatography on silica gel. Preferably, the mixture of ginsenosides is enriched in Rb.sub.1 by partition between an aqueous system and water ethyl acetatebutanol.
    Type: Grant
    Filed: September 13, 1991
    Date of Patent: August 11, 1992
    Inventors: Peter K. T. Pang, Lawrence C. H. Wang, Christina G. Benishin, Hsing J. Liu
  • Patent number: 5130420
    Abstract: A process is described for the production of an alkyl glycoside which comprises distilling a higher alcohol in the presence of an alkaline substance, or washing a higher alcohol with an aqueous solution of an alkaline substance, and then reacting the higher alcohol with a sugar or a reaction product of a sugar and a lower alcohol. According to this process, an alkyl glycoside showing an excellent hue can be produced by repeatedly using unreacted alcohol recovered from the reaction mixture in the production of an alkyl glycoside.
    Type: Grant
    Filed: March 16, 1990
    Date of Patent: July 14, 1992
    Assignee: Kao Corporation
    Inventors: Akira Yamamuro, Toyomi Koike, Hiroki Sawada, Akio Kimura
  • Patent number: 5128323
    Abstract: The invention relates to pharmaceutical compositions having antiendotoxic activity, comprising as the active component a fraction which can be isolated from lactulase syrup by means of absorption at a sulphonated polystyrene cation resin in the Ca.sup.2+ - form and elution with a suitable solvent. The lactulose syrup can be obtained by basic isomerization of lactose at elevated temperature, optionally in the presence of sodiumsulphite.
    Type: Grant
    Filed: May 23, 1989
    Date of Patent: July 7, 1992
    Assignee: Duphar International Research B.V.
    Inventor: Maarten H. Pranger
  • Patent number: 5126244
    Abstract: A method for the liberation of polysaccharide antigens from bacteria or fungi in biological probes or in grown cultures of these probes is described. In the majority of cases such a liberation is necessary in order that subsequently the polysaccharide antigens can be determined immunologically in a manner known per se. This liberation is effected by treating the biological probe or the grown culture with an aqueous phenol solution. A 1-10% phenol solution is conveniently used, with a 2.5% phenol solution being preferred and a 2% phenol solution being especially preferred. The phenol solution is allowed to act on the probe or culture for 5-30%, preferably 15, minutes. No extraction is necessary for the subsequent immunological determination of the polysaccharides.
    Type: Grant
    Filed: November 17, 1988
    Date of Patent: June 30, 1992
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Hanne-Lene Muller
  • Patent number: 5122371
    Abstract: A biologically active agent extracted from female breast cyst fluids displays anti-hypertensive activity in mammals. The agent is also useful in the treatment of congestive heart disease, artial fibrillation and idiopathic edema in mammals.
    Type: Grant
    Filed: March 6, 1991
    Date of Patent: June 16, 1992
    Inventors: Fred I. Chaslow, H. Leon Bradlow
  • Patent number: 5116969
    Abstract: The invention is a very highly refined arabinogalactan gum falling within the molecular weight range of 6,000-2,500,000 and having a tannic acid equivalent of less than about 0.5 mg/g. The preferred product will have a molecular weight within the range of 6,000-1,300,000 and tannic acid equivalent no higher than about 0.25. The product is nearly colorless and is tasteless and odorless. it is prepared by first making a crude water extract of a natural source such as larch wood. This extract is next refined by the addition of an active MgO to precipitate the bulk of the lignans and iron containing compounds. Following that it is processed through a membrane no larger than about 0.45 .mu.m to remove any species having molecular weights in excess of about 2,500,000. The permeate may then be treated on successively smaller membranes down to about 6,000 daltons.
    Type: Grant
    Filed: April 26, 1990
    Date of Patent: May 26, 1992
    Assignee: Larex International, Inc.
    Inventors: Mark F. Adams, Melvin R. Knudson
  • Patent number: 5112407
    Abstract: There is provided a process to prepare maltose powder containing crystalline beta-maltose hydrate, comprising concentrating an aqueous solution of a high-purity maltose having a maltose content of at least 85% DS to a moisture content below 10 w/w %, partially crystallizing alpha-maltose in the syrup, and crystallizing beta-maltose hydrate in the same syrup while converting the resultant crystalline alpha-maltose into crystalline beta-maltose hydrate. Use of the invention enables consistently high-quality maltose powders at a reduced drying cost.
    Type: Grant
    Filed: May 22, 1990
    Date of Patent: May 12, 1992
    Assignee: Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo
    Inventors: Shuzo Sakai, Hiroshi Akai, Toshio Miyake
  • Patent number: 5112964
    Abstract: The present invention provides a process of producing a water-soluble hemicellulose comprising a starch removing stage, an extraction stage and a neutralization and desalting stage and the use of the obtained water-soluble hemicellulose as a health food.
    Type: Grant
    Filed: November 29, 1989
    Date of Patent: May 12, 1992
    Assignee: Snow Brand Milk Products Co., Ltd.
    Inventors: Seiichiro Aoe, Taishi Oda, Masanori Nakaoka, Seiji Kurosawa
  • Patent number: 5109127
    Abstract: A nonionic surface active agent comprising a fatty acid ester of a hexose sugar or an alkyl glycoside thereof, wherein the content of monoester is from 93 to 99.9% by weight, the content of diester is from 0.1 to 7% by weight and the content of tri- and higher polyesters is from 0 to 1% by weight in the fatty acid ester.
    Type: Grant
    Filed: November 5, 1990
    Date of Patent: April 28, 1992
    Assignee: Lion Corporation
    Inventors: Shizuo Sekiguchi, Tomoko Yasumasu, Hiroshi Miyake, Yoshihisa Endo
  • Patent number: 5106966
    Abstract: The invention describes a method for extracting DNA from a sample. It involves contacting a sample with a separation reagent which permits differentiated solvation of DNA and protein. By adding a gel polymer, such as a polyester gel polymer to the mixture of sample and separating reagent followed by agitation via, e.g., centrifugation, the DNA and protein are separated, with the gel acting as a block to prevent contamination of the DNA phase by the protein. Higher yields of DNA are obtained as compared to methodologies where the gel is not used. Additionally, the problems associated with the physical contact of the solvents, which are frequently carcinogens, are avoided. Also taught are kits which can be used in connection with the inventive method.
    Type: Grant
    Filed: July 10, 1989
    Date of Patent: April 21, 1992
    Assignee: University of Kansas
    Inventors: Stanley Thomas, Lowell Tilzer, Ruben Moreno
  • Patent number: 5104981
    Abstract: A process is disclosed for the production of an alkyl glycoside excellent in hue, which comprises (1) reacting a sugar with alcohol to obtain an alkyl glycoside reaction product containing an unreacted higher alcohol, (2) reacting the resulting product with a metal/hydrogen complex represented by formula (I)M(BH.sub.4).sub.x (I)whereinM is an alkali metal, Ca, Zn, or (CH.sub.3).sub.4 N; and x is 1 when M is an alkali metal or (CH.sub.3).sub.4 N and x is 2 when M is Ca or Zn;(3) separating the resulting reaction mixture into the alkyl glycoside and the unreacted higher alcohol, and (4) decomposing the remaining metal/hydrogen complex with an acid.
    Type: Grant
    Filed: March 16, 1990
    Date of Patent: April 14, 1992
    Assignee: Kao Corporation
    Inventors: Akira Yamamuro, Makoto Amau, Tadaaki Fujita, Kiyoshi Aimono, Akio Kimura
  • Patent number: 5094740
    Abstract: Separation methodology is disclosed which allows for the separation of mixtures of carbohydrates into highly resolved detectable bands of carbohydrates. The method involves first reacting a mixture of carbohydrates with charge generating moieties which are capable of fluorescing such as 1-amino-4-naphthalene sulfonic acid (ANSA) to form carbohydrate conjugates. The conjugates are subjected to a first-dimensional gel electrophoresis in a first direction to provide separate bands of carbohydrates in the gel. A band in the gel is removed and subjected to second-dimensional electrophoresis in a second direction which is substantially perpendicular to the first direction. More specific bands of more highly resolved carbohydrates are then formed in the second-dimensional gel. The more specific bands within the second-dimensional gel are then electro-blotted onto a substrate surface and can be viewed in extremely small amounts due to the fluorescent capability of the ANSA when viewed under ultraviolet light.
    Type: Grant
    Filed: September 27, 1990
    Date of Patent: March 10, 1992
    Assignee: Glycomed, Inc.
    Inventors: Brian K. Brandley, Robert J. Stack
  • Patent number: 5094731
    Abstract: Saccharide in mixtures are separated into groups or individual saccharides and tested for their affinity for particular proteins. The method of the invention is carried out by conjugating saccharides in a mixture with charge-generating moieties and moieties capable of fluorescing such as 4-amino-1-naphthalene sulfonic acid (ANSA) to form conjugates. The saccharide conjugates are subjected to electrophoretic resolution within gels. The resolved bands of material can be seen under ultraviolet light and are electro-blotted onto charged nylon membranes to provide a stable record of the electrophoretic separation. The blots (visible under ultraviolet light) on the nylon membranes are brought into contact with particular proteins in order to determine the binding affinity of these particular proteins to particular saccharides on the nylon membrane. The proteins are preferably bound to labels so that the binding of the proteins to the saccharides can be easily detected.
    Type: Grant
    Filed: September 27, 1990
    Date of Patent: March 10, 1992
    Assignee: Glycomed, Inc.
    Inventors: Brian K. Brandley, Paul G. James, Michael Tiemeyer
  • Patent number: 5093244
    Abstract: A process for the fermentative production of the deoxyribonucleoside thymidine and/or its corresponding base thymine by aerobically cultivating a strain of the genus Brevibacterium, in particular one of the strains NCIMB 40117 and 40116. The produced thymidine may be used as an intermediate in the production of azidothymidine and active ingredient in a composition for use in the treatment of auto imune deficiency syndrome (AIDS). Biologically pure cultures of strain NCIMB 40014 and variants and mutants derived therefrom are claimed per se.
    Type: Grant
    Filed: May 22, 1989
    Date of Patent: March 3, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventor: Linda A. Naylor
  • Patent number: 5093487
    Abstract: The present disclosure is concerned with procedures for adjusting the average molecular weight, the molecular weight distribution and the viscosity in solution of hyaluronic acid and its salts (HA), particularly its sodium and potassium salts. The average molecular weight can be increased and the molecular weight distribution can be narrowed by precipitating this material into a bath of a non-solvent containing a continuously moving device to which it can adhere as it precipitates. The solution viscosity of this or any high molecular weight, high viscosity HA can be reduced without substantially effecting its molecular weight by either a moderate temperature heat treatment or passage through a fine (one micron or less) pore filter as a one weight percent or stronger aqueous solution. The disclosure is also concerned with the high molecular weight low solution viscosity HA so obtained.
    Type: Grant
    Filed: January 6, 1986
    Date of Patent: March 3, 1992
    Assignee: Mobay Corporation
    Inventors: Karen K. Brown, Nathan D. Greene, Sandy L. Trump, Sharon A. Bryant
  • Patent number: 5089401
    Abstract: An enzymatic method for the preparation of a fructose-containing oligosaccharide, in which a .beta.-fructofuranosidase obtained by culturing Arthrobacter sp. K-1 (FERM BP-3192) as an enzyme is reacted on sucrose, raffinose or stachyose as the donor in the presence of an aldose or ketose as the receptor. The enzyme is characterized by:(1) activity on sucrose for the transglycosidation of a fructosyl group to the receptor in the presence of a monosaccharide, sugar alcohol, alkyl alcohol, glycoside or oligosaccharide;(2) activity for the decomposition of sucrose, elrose, neokestose, xylsucrose, raffinose and stachyose with inactivity on a saccharide selected from the group consisting of 1-kestose, nistose, inulobiose and levan biose;(3) optimum pH of 6.5 to 6.8 at 40.degree. C. with stability at a pH of 5.5 to 10;(4) optimum temperature of 55.degree. C. at a pH of 6.5 exhibiting at least 70% of residual activity at 60.degree. C.
    Type: Grant
    Filed: March 20, 1991
    Date of Patent: February 18, 1992
    Assignee: Ensuiko Sugar Refining Co., Ltd.
    Inventors: Koki Fujita, Kozo Hara, Hitoshi Hashimoto, Sumio Kitahata
  • Patent number: 5089607
    Abstract: The residual flow of the starch preparation from wheat, rye, oats or barley is thickened to a dry material content of 17 to 25 weight % after which an enzyme preparation with pentosanase activity, originating from fungi or yeasts, is added. The enzyme preparation is allowed to react for 0.5 to 4 hours with a pH of 2.6 to 3.7 and at a temperature between 30 and 50.degree. C. and the starch fraction is separated afterward with an increased yield. The starch thus obtained is a calibrated, fine grained starch of which at least 90 weight % of the grains have a diameter of 3 to 12 micrometer.
    Type: Grant
    Filed: December 21, 1989
    Date of Patent: February 18, 1992
    Assignee: Amylum, naamloze vennootschap
    Inventors: Luc E. Boni, Frank R. Van Lancker
  • Patent number: 5087337
    Abstract: A method of separating mixtures of saccharides into distinct detectable groups is disclosed. In accordance with the method a tri-functional conjugate must first be provided. The tri-functional conjugate is obtained by reacting a mixture of saccharides with moieties (a) capable of providing a charge upon ionization; (b) capable of fluorescing under ultraviolet light; and (c) having a light-activatable azido group thereon. The different functional moieties may all be present on the same moiety and connected directly to the saccharide or may be connected to each other wherein only one of the moieties is connected directly to the saccharide. The tri-functional conjugates are subjected to electrophoretic separation to obtain separate groups of conjugates in the gel. The groups of conjugates are transferred from the gel to the surface of a membrane which is exposed to light for a sufficient time and light frequency to activate the azido-group.
    Type: Grant
    Filed: September 27, 1990
    Date of Patent: February 11, 1992
    Assignee: Glycomed, Inc.
    Inventors: Brian K. Brandley, Michael Tiemeyer, Robert J. Stack
  • Patent number: 5084564
    Abstract: The process makes an oligosaccharide fraction from commerically available heparin solutions containing from 1 to 10 % heparin. This oligosaccharide fraction has antithrombotic activity, bioavailability, almost no toxic effects as well as a comparatively lower hemorrhagic risk and a reduction in bleeding time and a molecular weight range of less than 5000 D.
    Type: Grant
    Filed: April 10, 1989
    Date of Patent: January 28, 1992
    Assignee: Bioiberica, S.A.
    Inventors: Francisco J. P. Vila, Alberto D. Nusimovich, Pedro T. Gomis
  • Patent number: 5078796
    Abstract: A process is disclosed for the synthesis of D-tagatose by isomerizing a mixture containing D-galactose with a metal hydroxide in the presence of a catalyst at a relatively low temperature to form an intermediate metal hydroxide-D-tagatose complex, and then neutralizing the intermediate with acid to yield D-tagatose. The method is also suitable for the synthesis of L-tagatose from L-galactose, and for the recovery of pure tagatose from crude tagatose syrups. Whey, deproteinized whey, or lactose may be used as the raw material for the D-galactose. The lactose in such cases is hydrolyzed to D-galactose and D-glucose before the isomerization step.
    Type: Grant
    Filed: March 25, 1991
    Date of Patent: January 7, 1992
    Assignee: Biospherics Incorporated
    Inventors: James R. Beadle, James P. Saunders, Thomas J. Wajda, Jr.
  • Patent number: 5077398
    Abstract: This invention relates to a novel process for isolation and purification of avermectin compounds which are produced by the microorganism, Streptomyces avermitilis. The process disclosed herein involves two steps, namely, crude crystallization and recrystallization. The isolated compounds are described generically as avermectin B1 and B2 and have significant parasiticidal activity.
    Type: Grant
    Filed: November 18, 1986
    Date of Patent: December 31, 1991
    Assignee: Merck & Co., Inc.
    Inventor: Frank J. Matthews
  • Patent number: 5075430
    Abstract: This invention is directed to a process for the purification of plasmid and other DNA, both single-stranded and double-stranded, by immobilizing the DNA onto diatomaceous earth in the presence of a chaotropic agent and eluting the DNA with water or low salt buffer. The resulting purified DNA is biologically active. Also included in the invention is a process for the immobilization of DNA onto diatomaceous earth in the presence of a chaotropic agent.
    Type: Grant
    Filed: December 18, 1990
    Date of Patent: December 24, 1991
    Assignee: Bio-Rad Laboratories, Inc.
    Inventor: Michael C. Little
  • Patent number: 5062959
    Abstract: Enrichment and purification of heart glycosides from mixtures of mother liquors is achieved by absorption on non-polar, large-pored resins from aqueous solution with possible addition of solvents miscible with water, and subsequent desorption with water/solvent mixtures or pure solvents.
    Type: Grant
    Filed: September 7, 1990
    Date of Patent: November 5, 1991
    Assignee: Boehringer Mannheim GmbH
    Inventors: Carl H. Ross, Rudolf Machat, Werner Haring, Gustav Lettenbauer
  • Patent number: 5055571
    Abstract: The present invention pertains to a method of purifying crude polyol fatty acid polyesters, in particular sugar polyesters, comprising, preferably more than one, alkaline washing treatments at pH of at least 12.5, optionally in combination with water and/or acid washing treatments and further conventional refining steps. By this method better color-removal and stability against high-temperature discoloring is achieved.
    Type: Grant
    Filed: December 5, 1988
    Date of Patent: October 8, 1991
    Assignee: Van den Bergh Foods Co., Division of Conopco Inc.
    Inventor: Gerard J. Van Lookeren
  • Patent number: 5051408
    Abstract: A process for preparing gamma inulin comprising the steps of (a) recrystallizing crude inulin from water at a temperature below 37.degree. C. to obtain a suspension, (b) heating the suspension at a temperature of from about 25.degree. to 45.degree. C. for about 1-3 days, (c) further heating the suspension at a temperature of about 40.degree. to 55.degree. C. for about 0.5 to 1.5 hours, and (d) isolating insoluble gamma inulin from the suspension. A composition comprising particles of inulin or an inulin derivative in the gamma polymorphic form is characterized in that the particles have a low rate of solution in aqueous media above 30.degree. C., particularly above 37.degree. C. The composition is effective as the active component of an immunotherapeutic preparation for activation of the alternative pathway of complement, or for antitumor treatment.
    Type: Grant
    Filed: March 30, 1990
    Date of Patent: September 24, 1991
    Assignee: The Australian National University
    Inventor: Peter Dodd Cooper
  • Patent number: 5043287
    Abstract: The instant invention is a process for the recovery from an aqueous solution of water soluble biopolymers, in particular polysaccharides, gums, agar, agarose and starches by the addition of polyoxide solution to the biopolymer containing solution. The biopolymer is then separated and collected.
    Type: Grant
    Filed: May 16, 1989
    Date of Patent: August 27, 1991
    Assignee: The Standard Oil Company
    Inventor: S. S. Johal
  • Patent number: 5041544
    Abstract: A method of preparing crystals of a glucosylmoranoline formula (III) ##STR1## wherein R is hydrogen or lower alkyl by fractional cyrstallizatin using a polar solvent and an arylsulfonic acid.
    Type: Grant
    Filed: April 15, 1987
    Date of Patent: August 20, 1991
    Assignee: NipponShinyaku Co., Ltd.
    Inventors: Yoji Ezure, Katsunori Miyazaki, Makoto Sugiyama
  • Patent number: 5035786
    Abstract: A method of separating mixtures of saccharides into distinct detectable groups is disclosed. The method comprises modifying 1-amino-4-naphthalene sulfonic acid (ANSA) with a light-sensitive azido-group and binding the modified ANSA to saccharides to form ANSA/saccharide conjugates. The conjugates are subjected to electrophorectic separation to obtain separate groups of conjugates in the gel. The groups of conjugates are transferred from the gel to the surface of a membrane which is exposed to light for a sufficient time and light frequency to activate the azido-group. The light-activated azido-groups attached to the surface of the membrane. The ANSA/saccharides conjugates can then be contacted with labeled probes such as radiolabeled proteins to determine the affinity of the probes to particular saccharides.
    Type: Grant
    Filed: February 16, 1990
    Date of Patent: July 30, 1991
    Assignee: Glycomed, Incorporated
    Inventors: Brian K. Brandley, Michael Tiemeyer
  • Patent number: 5034515
    Abstract: A purified fibronectin receptor polysaccharide derived from Staphylococcus aureus is useful as an antigen for diagnostic tests and the preparation of monoclonal antibodies. The fibronectin receptor polysaccharide is prepared by gently removing expresed material, including the polysaccharide, from the cell surfaces of the S. aureus without killing the cells followed by purification. Monoclonal antibodies directed against the polysaccharide can be used in methods of preventing or treating S. aureus infections by administering the monoclonal antibodies to animals.
    Type: Grant
    Filed: September 22, 1987
    Date of Patent: July 23, 1991
    Assignee: Wisconsin Alumni Research Foundation
    Inventor: Richard A. Proctor
  • Patent number: 5034520
    Abstract: The oligosaccharides of the invention are composed essentially of chains:possessing a specific affinity for the anionic and cationic cell growth factor which recognize herparin,comprising at least one sequence of 5 residues matching those present in naturally occurring heparin and possessing a strongly anionic character such as that indicated in the NMR spectrum shown in FIG. 1, as well as their pharmacologically acceptable salts.
    Type: Grant
    Filed: April 16, 1987
    Date of Patent: July 23, 1991
    Assignee: Sanofi
    Inventors: Jean-Claude Lormeau, Maurice Petitou, Jean Choay
  • Patent number: 5028438
    Abstract: A biologically active agent extracted from female breast cyst fluids displays anti-hypertensive activity in mammals. The agent is also useful in the treatment of congestive heart disease, atrial fibrillation and idiopathic edema in mammals.
    Type: Grant
    Filed: December 9, 1987
    Date of Patent: July 2, 1991
    Assignee: Long Island Jewish Medical Center
    Inventors: Fred I. Chaslow, H. Leon Bradlow
  • Patent number: 5023330
    Abstract: Process of preparing 1,6-.beta.-D-anhydroglucopyranose (levoglucosan) in high purity is described, where the starting material with a water-content, adjusted to max. 20%, is pyrolyzed, the volatile components are condensed and this distillate is neutralized. After filtration and optional treatment with an adsorbent, the mixture is chromatographically separated over an ion-exchange resin with water as eluent. Levoglucosan containing fractions are concentrated and crystalline levoglucosan is obtained by an evaporation - and/or cooling crystallization from a supersaturated water solution.
    Type: Grant
    Filed: January 30, 1989
    Date of Patent: June 11, 1991
    Assignee: Suedzucker-Aktiengesellschaft
    Inventors: Michael Gander, Knut M. Rapp, Hubert Schiweck
  • Patent number: 5019269
    Abstract: These resins derived from a crosslinked styrene (co)-polymer, or from a crosslinked dextran, comprise a (co)-polymer chain which is substituted with one or more groups, which may be identical or different, belonging to the following categories: --Z--A.sub.1 ; --Z--A.sub.2 ; --Z--A.sub.1 --Z'--A.sub.2 ; --Z--A.sub.1 --A.sub.3 --A.sub.2 ; --Z--A.sub.1 --A.sub.4, where Z=spacer chain, Z'=linking chain, A.sub.1 =phosphate residue, A.sub.2 =residue of purine or pyrimidine base, A.sub.3 =sugar residue and A.sub.4 =residue of a molecule participating in the polar structure of various phospholipids. These resins are applicable for the analysis and purification of molecules of biological origin, in particular as a stationary phase in ion-exchange and affinity chromatography, especially for carrying out the fractionation of protein mixtures.
    Type: Grant
    Filed: March 21, 1990
    Date of Patent: May 28, 1991
    Assignee: Centre National de la Recherche Scientifique
    Inventors: Didier Letourneur, Colette Douzon, Veronique Migonney, Daniel A. Muller, Marcel Jozefowicz
  • Patent number: 5019231
    Abstract: Saccharide in mixtures are separated into groups or individual saccharides and tested for their affinity for particular proteins. The method of the invention is carried out by conjugating saccharides in a mixture with 4-amino-1-naphthalene sulfonic acid (ANSA) to form conjugates. The saccharide/ANSA conjugates are subjected to electrophoretic resolution within gels. The resolved bands of material are electro-blotted onto charged nylon membranes to provide a stable record of the electrophoretic separation. The blots on the nylon membranes are brought into contact with particular proteins in order to determine the binding affinity of these particular proteins to particular saccharides on the nylon membrane. The proteins are preferably bound to labels so that the binding of the proteins to the saccharides can be easily detected.
    Type: Grant
    Filed: February 16, 1990
    Date of Patent: May 28, 1991
    Assignee: Glycomed, Incorporated
    Inventors: Brian K. Brandley, Paul G. James, Michael Tiemeyer
  • Patent number: 5017697
    Abstract: A process for recovering, in a purified form, sucrose fatty acid esters having a high HLB included in a reaction mixture formed by a reaction of sucrose and a fatty acid alkyl ester in an organic solvent as reaction medium in the presence of a catalyst, which comprises adjusting the reaction mixture from which a part of the organic solvent may be previously removed and to which water is added to form an aqueous solution, to a neutral pH region, adding a neutral salt and sucrose to the solution to precipitate the sucrose fatty acid esters, separating and washing the precipitate with an acidic water, and subjecting the washing liquid to ultrafiltration. The concentrate obtained by ultrafiltration may be spray-dried to form a dry powder of the sucrose esters having high HLB, and the liquid obtained by separating the precipitate may be contacted with a reverse osmosis membrane to recover sucrose.
    Type: Grant
    Filed: June 28, 1989
    Date of Patent: May 21, 1991
    Assignee: Dai Ichi Kogyo Seiyaku Co., Ltd.
    Inventors: Shusaku Matsumoto, Yoshio Hatakawa, Akihiko Nakajima
  • Patent number: 5011922
    Abstract: A process for purifying sucrose fatty acid esters included in a reaction mixture formed by a reaction of sucrose and a fatty acid alkyl ester in an organic solvent as reaction medium in the presence of a catalyst, which comprises adjusting the reaction mixture from which a part of the organic solvent as reaction medium may be previously removed and to which water is added to form an aqueous solution, to a neutral pH region, adding a neutral salt and sucrose to the solution to precipitate the sucrose fatty acid ester, filtering off the precipitate, and washing the precipitate with an acidic water. The washed precipitate in the form of slurry is spray-dried to form a dry powder, and the filtrate is contacted with a reverse osmosis membrane to recover sucrose. According to the invention, purified sucrose fatty acid esters can be obtained from the reaction mixture without using an organic solvent as purification solvent, while sucrose can be recovered in high yield.
    Type: Grant
    Filed: June 23, 1989
    Date of Patent: April 30, 1991
    Assignee: Dai-Ichi Kogyo Seiyaku Co., Ltd.
    Inventors: Shusaku Matsumoto, Yoshio Hatakawa, Akihiko Nakajima
  • Patent number: 5011919
    Abstract: The present invention relates to modified heparins having antithrombotic activity.The invention also relates to a process of preparing such modified heparins starting from water insoluble heparin ammonium quaternary complexes.Finally, the invention relates to pharmaceutical compositions containing the above modified heparins.
    Type: Grant
    Filed: January 27, 1989
    Date of Patent: April 30, 1991
    Assignee: Ajorca S.A.
    Inventors: Fernando Fussi, Victor B. Diaz, Richardo H. Domanico
  • Patent number: 5008387
    Abstract: From a reaction mixture obtained by reaction of sucrose and a fatty acid alkyl ester in the presence of a catalyst, a purified sucrose fatty acid ester is prepared without using organic solvents for purification by adding water to the reaction mixture and subjecting the resulting aqueous solution to ultrafiltration, thereby removing the unreacted sucrose, the catalyst or a salt derived from the catalyst, and the volatile component used as the reaction medium together with water. A powder of the purified sucrose fatty acid ester is easily, economically and safely prepared by subjecting the aqueous solution remaining in the ultrafiltration to reverse osmosis and spray-drying the resulting concentrate.
    Type: Grant
    Filed: April 14, 1989
    Date of Patent: April 16, 1991
    Assignee: Dai-Ichi Kogyo Seiyaku Co., Ltd.
    Inventors: Shusaku Matsumoto, Yoshio Hatakawa, Akihiko Nakajima
  • Patent number: 5003061
    Abstract: A method for preparing high-purity crystalline lactulose and the product obtained by the method, which comprises crystallization from aqueous solutions at a temperature of 5.degree.-40.degree. C., the starting aqueous solution having a lactulose concentration of 50-80% w/w, a lactose concentration of less than 5% of the lactulose concentration by weight, a galactose concentration of less than 5% of the lactulose concentration by weight, and a concentration of other sugars of less than 4% of the lactulose concentration by weight.
    Type: Grant
    Filed: January 11, 1988
    Date of Patent: March 26, 1991
    Assignee: SIRAC Srl
    Inventors: Renato Carobbi, Franco Innocenti
  • Patent number: 4997923
    Abstract: The present invention provides novel dihydrate crystals of etoposide-2-dimethylamino compound hydrochloride [4'-demethylepipodophillotoxin 9-(4,6-O-ethylidene-2-dimethylamino-2-deoxy-.beta.-D-glucopyranoside hydrochloride] used as a carcinostatic agent and a process for production thereof.
    Type: Grant
    Filed: November 13, 1989
    Date of Patent: March 5, 1991
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Takao Izawa, Tadashi Fujii, Yukio Chikui, Kazuo Ohtsuki
  • Patent number: 4997927
    Abstract: A process for the purfication of synthetic oligonucleotides is described which drastically simplifies the hitherto very time consuming purification process. The deprotection solution is adsorbed without being concentrated on a carrier having reversed phase properties and optionally ion exchanger properties, the oligonuleotides without lipophilic protecting group are removed, their protecting group is cleaved off from the adsorbed oligonucleotides, the adsorbed oligonucleotides are washed and eluted from the carrier and then purified in a manner known per se.
    Type: Grant
    Filed: August 27, 1985
    Date of Patent: March 5, 1991
    Assignee: Gesellschaft fur Biotechnologische Forschung mbH (GBF)
    Inventors: Helmut Blocker, Ronald Frank, Gudrun Heisterberg-Moutsis, Gisela Kurth, Andreas Meyerhans
  • Patent number: 4996309
    Abstract: A process for preparing sucrose fatty acid esters by reacting sucrose and a fatty acid alkyl ester in an aqueous reaction system in the presence of a catalyst, adding water to the reaction mixture to dissolve it, adjusting the reaction mixture to a neutral ph region, adding a neutral salt to the solution to precipitate the sucrose fatty acid esters, separating and washing the precipitate with an acidic water, and subjecting the washing liquid to ultrafiltration. The precipitate washed with the acidic water is spray-dried in the form of an aqueous slurry to give a dry powder of the sucrose esters having low HLB, and the concentrate obtained by ultrafiltration is spray-dried to form a dry powder of the sucrose esters having high HLB, and the liquid obtained by separating the precipitate is contacted with a reverse osmosis membrane to recover sucrose. According to the invention, purifed sucrose fatty acid esters can be obtained without using an organic solvent, while sucrose can be recovered in high yield.
    Type: Grant
    Filed: October 3, 1989
    Date of Patent: February 26, 1991
    Assignee: Dai-Ichi Kogyo Seiyaku Co., Ltd.
    Inventors: Shusaku Matsumoto, Yoshio Hatakawa, Akihiko Nakajima
  • Patent number: 4995911
    Abstract: A process for recovering unreacted sucrose from a reaction mixture of sucrose and a fatty acid alkyl ester in an organic solvent as reaction medium in the presence of a catalyst in the production of a sucrose fatty acid ester which comprises adjusting the reaction mixture from which a part of the organic solvent as reaction medium may be previously removed and to which water is added, to a neutral pH region, adding a neutral salt and sucrose to the reaction mixture to precipitate the sucrose fatty acid ester, filtering off the precipitate, and bringing the filtrate into contact with a reverse osmosis membrane to recover the unreacted sucrose. According to the invention, unreacted sucrose can be easily recovered, while the sucrose fatty acid ester not contaminated with the organic solvent as reaction medium can be obtained from the reaction mixture without using an organic solvent for purification.
    Type: Grant
    Filed: June 13, 1989
    Date of Patent: February 26, 1991
    Assignee: Dai-Ichi Kogyo Seiyaku Co., Ltd.
    Inventors: Shusaku Matsumoto, Yoshio Hatakawa, Akihiko Nakajima
  • Patent number: 4990611
    Abstract: Purified agarose is recovered from agar or impure agarose by dissolving the agar or agarose in a lower alkylene glycol at elevated temperature, cooling the agar- or agarose-containing glycol solution to induce precipitation of a purified agarose product, and recovering the precipitated agarose product.
    Type: Grant
    Filed: August 17, 1987
    Date of Patent: February 5, 1991
    Assignee: FMC Corporation
    Inventor: Richard B. Provonchee