Sulfur Or Halogen Containing Patents (Class 536/122)
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Patent number: 4985550Abstract: Compounds having a polyhydroxylated hydrophilic moiety, a highly fluorinated moiety and a functional junction group linking said moieties together, wherein said hydrophilic moiety is derived from a polyol or an aminopolyol, and wherein said highly fluorinated moiety consists of a fluorocarbon group wherein at lest 50% of the atoms bonded to the carbon skeleton are fluorine atoms, the other atoms bonded to the carbon skeleton being hydrogen, chlorine or bromine atoms, said highly fluorinated moiety containing at least 4 fluorine atoms; as well as the internal ethers and ketals thereof; process for their preparation; and a compositions containing said compounds as surfactants, together with non polar compounds, for use as gas carriers.Type: GrantFiled: July 28, 1987Date of Patent: January 15, 1991Assignee: Alliance Pharmaceutical Corp.Inventors: Brigitte Charpiot, Jacques Greiner, Maurice Le Blanc, Alexandre Manfredi, Jean Riess, Leila Zarif
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Patent number: 4983724Abstract: A process and intermediates useful for the invrsion of 2-deoxy-2,2-difluororibose analogs to provide 2-deoxy-2,2-difluoroxylose analogs is described.Type: GrantFiled: August 15, 1989Date of Patent: January 8, 1991Assignee: Eli Lilly and CompanyInventors: Larry W. Hertel, Marie T. Reamer
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Patent number: 4980462Abstract: A second-step virus binding receptor is found in nature on the surface of animal and plant cells. This receptor is thought to be needed for virus penetration into target cells. The second-step receptor has been found to bind a wide variety of viruses belonging to a number of different families. The second-step receptor and natural or synthetic substances which correspond to or are analogous to the binding epitope of the second-step receptor in that they are able to bind to a site on the virus which recognizes the binding epitope of the natural second-step receptor, are therefore indicated for the diagnosis, prophylaxis or treatment of viral infections.Type: GrantFiled: June 19, 1989Date of Patent: December 25, 1990Assignee: Symbicom AktiebolagInventors: Karl-Anders Karlsson, Erling Norrby, Goran Wadell
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Patent number: 4980463Abstract: A process for the chlorination of sucrose-6-esters to produce 6',4,1'-trichlorosucrose-6-esters which comprises the steps of:(a) adding at least seven molar equivalents of an acid chloride to a reaction mixture containing a sucrose-6-ester and a tertiary amide to form initially a chloroformiminium chloride salt which subsequently forms a complex with the hydroxyl groups of the sucrose-6-ester;(b) subjecting the reaction mixture product of step (a) to an elevated temperature not higher than about 85.degree. C. for a period of time sufficient to produce a mixture of chlorinated sucrose-6-ester products consisting essentially of 6'-chlorosucrose-6-ester, 4,6'-dichlorosucrose-6-ester, and 1',6'-dichlorosucrose-6-ester; and(c) subjecting the reaction mixture product of step (b) to an elevated temperature not higher than about 125.degree. C. for a period of time sufficient to produce a chlorinated product consisting essentially of 1',4,6'-trichlorosucrose-6-ester.Type: GrantFiled: July 18, 1989Date of Patent: December 25, 1990Assignee: Noramco, Inc.Inventors: Robert E. Walkup, Juan L. Navia, Nicholas M. Vernon
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Patent number: 4978748Abstract: Processes for producing antibacterial and antitumor agents designated LL-E33288.epsilon.-I and LL-E33288.epsilon.-Br using triphenylphosphine at ice bath temperature are disclosed. Novel intermediates prepared in the processes are also disclosed.Type: GrantFiled: February 29, 1988Date of Patent: December 18, 1990Assignee: American Cyanamid CompanyInventors: George A. Ellestad, William J. McGahren
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Patent number: 4977253Abstract: An alkyloligoglycoside having an alkyl group content of 8 to 22 carbon atoms and having an average degree of oligomerization of 1 to 5 is sulfated with a sulfating agent in an organic solvent having a boiling point of 30.degree. to 100.degree. C.Type: GrantFiled: August 2, 1989Date of Patent: December 11, 1990Assignee: Huels AktiengesellschaftInventor: Norbert Ripke
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Patent number: 4977143Abstract: Antibacterial and antitumor agents designated LL-E333288.epsilon.-I and LL-E33288.epsilon.-Br and their production by strains of Micromonospora echinospora ssp. calichensis designated NRRL-15839, NRRL-15975 and NRRL-18149, are disclosed.Type: GrantFiled: February 29, 1988Date of Patent: December 11, 1990Assignee: American Cyanamid CompanyInventors: William J. McGahren, George A. Ellestad
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Patent number: 4977254Abstract: Sugars and partly protected sugar derivatives are chlorinated by reaction of unprotected hydroxyl groups with thionyl chloride to form a persulphite followed by decomposition of the sulphite groups to form chlorosulphites, displacement of the chlorosulphite groups and insertion of chlorine atoms at one or more positions, characterised in that formation and displacement of the chlorosulphite groups and insertion of chlorine atoms is effected by reaction with thionyl chloride in an inert solvent in the presence of a quaternary salt of the general formula:N.sup.+ R.sup.1 R.sup.2 R.sup.3 R.sup.4 Cl.sup.- (I)wherein R.sup.1, R.sup.2 and R.sup.3, which may be the same or different, each represent a lower alkyl group, and R.sup.Type: GrantFiled: August 2, 1989Date of Patent: December 11, 1990Assignee: Tate & Lyle PLCInventors: Nigel J. Homer, Graham Jackson, George H. Sankey, Philip J. Simpson
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Patent number: 4975531Abstract: The compounds of the formula I ##STR1## in which R.sub.1 to R.sub.3 denote, independently of one another, hydrogen or a (C.sub.1 -C.sub.18)-acyl group, and a process for the preparation thereof are described. These compounds have tumor-inhibiting properties.Type: GrantFiled: April 4, 1989Date of Patent: December 4, 1990Assignee: Behringwerke AktiengesellschaftInventors: Hans P. Kraemer, Lutz Robbel, Ludger M. Schwenen
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Patent number: 4973686Abstract: The invention relates to the use of selected carboxylic acid esters which are liquid under reaction conditions and correspond to general formula (I)X--COOR.sup.1 (I)in which R.sup.1 is an alkyl radical unbranched in the .alpha.-position and X is hydrogen or a group corresponding to general formula (II) ##STR1## in which R.sup.2, R.sup.3 and R.sup.4 represent fluorine and/or chlorine and one of these substituents may also be hydrogen or one or two of these substituents may also be lower alkyl, as reaction medium for the sulfonation and/or sulfatization or organic components with SO.sub.3 to light-colored reaction products.Type: GrantFiled: September 2, 1988Date of Patent: November 27, 1990Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Josef Kretschmann, Franz-Josef Carduck, Willi Wuest, Hubert Harth, Dirk Springer
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Patent number: 4956459Abstract: Compounds of the formula: ##STR1## wherein each of R.sub.1 and R.sub.2 is independently selected from the group consisting of halogen, hydroxy, or mono carboxylic acid or R.sub.1 and R.sub.2 together is a multifunctional carboxylic acid residue which forms a ring with the platinum atom through two oxygens of said multifunctional carboxylic acid; R.sub.3 is a deoxy mono or disaccharide or a derivative thereof; and R.sub.4 is selected from the group consisting of hydrogen, C.sub.1-4 -alkyl, phenyl, benzyl, substituted phenyl or substituted benzyl, wherein substituents are selected from the group consisting of halogen, nitro, C.sub.1-2 -alkoxy, carboxy, carbony ester or phenyl or a pharmaceutically acceptable salt thereof are disclosed. Compositions containing these compounds and methods using these compounds are also discussed.Type: GrantFiled: January 14, 1988Date of Patent: September 11, 1990Assignee: Georgetown UniversityInventors: Abdolhossen Talebian, Dianna C. Green, Charles F. Hammer, Philip S. Schein
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Patent number: 4954623Abstract: A process for recycling the difluoro sugar in the synthesis of 2,2-difluoronucleosides proceeds by removing the base moiety of .alpha.-difluoronucleosides by reduction and hydrolysis, followed by oxidation to put the difluro sugar in a form conventiently recycled into the synthesis, and intermediates useful therefor.Type: GrantFiled: November 13, 1989Date of Patent: September 4, 1990Assignee: Eli Lilly and CompanyInventor: Ramakrishnan Nagarajan
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Patent number: 4950746Abstract: Sucrose is reacted with a 1,3-di(hydrocarbyloxy)-1,1,3,3-tetra(hydrocarbyl)distannoxane to produce a 1,3-di-(6-O-sucrose)-1,1,3,3-tetra(hydrocarbyl)distannoxane, which can be acylated to produce a sucross-6-ester.Type: GrantFiled: July 18, 1988Date of Patent: August 21, 1990Assignee: Noramco, Inc.Inventor: Juan L. Navia
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Patent number: 4948881Abstract: Process for the depolymerization and sulfation of polysaccharides by reaction of said polysaccharides with a sulfuric acid/chlorosulfonic acid mixture.Type: GrantFiled: January 27, 1989Date of Patent: August 14, 1990Assignee: SanofiInventors: Annamaria Naggi, Giangiacomo Torri
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Patent number: 4948883Abstract: Bismuth salts of phosphorylated and/or sulfonated saccharides are prepared from a corresponding metal salt reactant, a water soluble organic acid, and a bismuth substance. For example, a complex salt of bismuth hydroxide sucrose octasulfate can be prepared in high yield and good purity from potassium sucrose octasulfate, trichloroacetic acid, trifluoracetic acid or 4-methylbenzenesulfonic acid, and bismuth hydroxide. Corresponding hydrogen phosphorylated and/or sulfonated saccharides may be intermediate products.Type: GrantFiled: October 31, 1989Date of Patent: August 14, 1990Assignee: Marion Laboratories, Inc.Inventor: Steven R. Duff
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Patent number: 4940786Abstract: Bismuth salts of phosphorylated and/or sulfonated saccharides can be prepared in one reaction vessel from a corresponding metal salt reactant, a water soluble organic acid, and a bismuth substance. For example, a complex salt of bismuth hydroxide sucrose octasulfate can be prepared in high yield and good purity from potassium sucrose octasulfate, trifluoracetic acid, and bismuth hydroxide.Type: GrantFiled: October 31, 1989Date of Patent: July 10, 1990Assignee: Marion Laboratories, Inc.Inventor: Steven R. Duff
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Patent number: 4939244Abstract: Degradation products, termed pseudaglycones, of LL-E33288, BBM-1675, FR-900405, FR-900406, PD 114759, PD 115028, CL-1577A, CL-1577B, CL-1577D, CL-1577E and CL-1724 antibiotics/antitumor agents are disclosed anad described.Type: GrantFiled: January 30, 1987Date of Patent: July 3, 1990Assignee: American Cyanamid CompanyInventor: May D.-M. Lee
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Patent number: 4935503Abstract: The invention describes a one-pot single step procedure for the azidochlorination or diazidization of glycals, including glycal elements of carbohydrates. Compounds such as 3,4,6-tri-O-benzyl-2-azido-2-deoxy-alpha-D-galactopyranosy chloride, and 3,4,6-tri-O-benzyl-2-azido-2-deoxy-alpha-,beta-D-galactopyranose are prepared from tri-O-benzyl galactal as well as 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-alpha-galactopyranasol chloride and 3,6-di-O-acetyl-4-O-[2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl]-2-azi do-2-deoxy-alpha-D-glycopyranosyl chloride from their respective O-acetylated glycal derivatives by the addition of azido chloride which is chemically generated in situ. A method using 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl chloride for the synthesis of antigenic determinants such as the terminal asialo GM.sub.1 (beta-D-Gal (1->3)-beta-D-GalNAc-OR) has been demonstrated.Type: GrantFiled: May 5, 1988Date of Patent: June 19, 1990Assignee: Biomira, Inc.Inventors: Selvaraj Naicker, Anthony A. Noujaim
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Patent number: 4935506Abstract: Sialic acid derivatives and process for preparing these compounds. In these compounds, a phenylthio group is stereo-selectively incorporated at the 3-position of the sialic acid. These compounds are useful as intermediates for synthesizing various glycosides such as ganglioside, a blood type determining factor, GQ.sub.1b etc. The present invention also relates to sialic acid-containing oligosaccharide derivatives and process for preparing them.Type: GrantFiled: June 12, 1989Date of Patent: June 19, 1990Assignee: MECT CorporationInventors: Toshio Goto, Tadao Kondo
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Patent number: 4925929Abstract: This invention relates to glucopyranose compounds of formula (I) and (IA) ##STR1## and the non-toxic salts thereof wherein the substituents are as defined herein. Such materials possess enhancing activity of cellular immunity (e.g. mitogenic activity) to living tissue and therefore are useful as anti-tumor agents.Type: GrantFiled: April 14, 1989Date of Patent: May 15, 1990Assignee: Ono Pharmaceutical Co. Ltd.Inventors: Masaaki Toda, Yutaro Sasaki, Katsuichi Shimoji
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Patent number: 4921950Abstract: This invention relates to a new synthetic process for the manufacture of zidovudine from the starting material D-xylose involving:(i) Conversion of D-xylose to a 1-(.beta.-D-xylofuranosyl)thymine derivative:(ii) 2'-Deoxygenation of the thymaine derivative; and(iii) 3'-Azidation of the 2'-deoxy compound.Type: GrantFiled: June 9, 1988Date of Patent: May 1, 1990Assignee: Burroughs Wellcome Co.Inventor: Jeffrey D. Wilson
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Patent number: 4920207Abstract: 2,3,4,3',4'-penta-O-acetyl sucrose (4-PAS), a key intermediate in the preparation of sucralose, is prepared by the selective removal of trityl groups from 6,1', 6'-tri-O-trityl-penta-O-acetyl sucrose (TRISPA) in which a catalytic amount of an aralkyl chloride or hydrogen chloride is added to a solution of TRISPA is an inert organic solvent is hydrogenated in the presence of a hydrogenolysis catalyst such a platinum or palladium.Type: GrantFiled: September 17, 1987Date of Patent: April 24, 1990Assignee: Tate & Lyle Public Ltd. Co.Inventors: George H. Sankey, Nigel J. Homer
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Patent number: 4918056Abstract: Novel arabinopyranosyl nucleoside derivatives having the heterocyclic moiety and fluorine at the 2' position of the sugar ring (pyranose configuration), which have antitumor, antiviral and antimicrobial properties, are prepared by condensation of a pyrimidine, purine or 1,3-oxazine base with an acylated 2-deoxy-2,2-difluoro-D-arabinopyranoside and/or acylated 2-deoxy-2-bromo-2-fluoro-D-arabinopyranoside.Type: GrantFiled: October 14, 1986Date of Patent: April 17, 1990Assignee: Health Research, Inc. (Roswell Park Division)Inventors: Miroslav V. Bobek, Seung-Ho An, Ralph J. Bernacki
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Patent number: 4918182Abstract: Crystalline sucralose having a mean particle size of at most 10 microns, the maximum particle size being no more than twice the mean, exhibits enhanced stability to heat. Preferably the sucralose has a mean particle size of at most 5 microns and a maximum particle size of at most 10 microns. A method of enhancing the thermal stability of crystalline sucralose comprises jet milling the sucralose to reduce the particle size, and render the size distribution such that the maximum size is no more than twice the mean.Type: GrantFiled: July 15, 1987Date of Patent: April 17, 1990Assignee: Tate & Lyle Public Limited CompanyInventors: Graham Jackson, Michael R. Jenner
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Patent number: 4916218Abstract: This invention relates to a new synthetic process for the manufacture of zidovudine from the starting material D-xylose involving:(i) Conversion of D-xylose to a 1-(.beta.-D-xylofuranosyl)thymine derivative;(ii) 2'-Deoxygenation of the thymine derivative; and(iii) 3'-Azidation of the 2'-deoxy compound.Type: GrantFiled: June 9, 1988Date of Patent: April 10, 1990Inventors: Merrick R. Almond, Jeffrey D. Wilson, Janet L. Rideout
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Patent number: 4916219Abstract: There is disclosed oligosaccharide compounds having heparin-like anticomplement activity and reduced anticoagulant activity as compared with heparin on a weight or molar basis. The oligosaccharide compounds have at least 5 and no greater than 25 saccharide units. The oligosaccharides can have an even nuber of saccharide units with a terminus nonreducing sugar, or an odd number of saccharide units without a terminus nonreducing sugar. There is also disclosed anticomplement pharmaceutical compositions with reduced anticoagulant side effect activity and a process for preparing the oligosaccharide compounds.Type: GrantFiled: August 2, 1988Date of Patent: April 10, 1990Assignee: University of Iowa Research FoundationInventors: Robert J. Linhardt, John M. Weiler
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Patent number: 4914196Abstract: Compounds of the formulae I and Ia ##STR1## in which R.sup.1 is a group which can be transferred to carbonyl or imine compounds, for example alkyl, allyl, vinyl or the radical of an enol or enamine, R.sup.2 is, for example, cyclopentadienyl, R.sup.3 is the radical of an optically active sugar or sugar derivative, Me is Ti, Zr or Hf, x is 0, 1 or 2 and y is 0, 1, 2 or 3, M.sup..sym. is Li.sup..sym., Na.sup..sym., K.sup..sym., MgY.sup..sym., ZnY.sup..sym., CdY.sup..sym., HgY, CuY.sup..sym. or quaternary ammonium, Y being halogen, are suitable for use as chiral reactants for compounds containing aldehyde, keto and/or N-substituted imine groups.Type: GrantFiled: February 27, 1989Date of Patent: April 3, 1990Assignee: Ciba-Geigy CorporationInventors: Martin Riediker, Robert W. Lang, Rudolf Duthaler, Peter Herold, Konrad Oertle, Guido Bold
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Patent number: 4914035Abstract: The present invention provides a process for selective production of a 2-.alpha.-O-glycoside compound of sialic acid which is useful as a starting material or intermediate for medicines and biochemical reagents. The process comprises reacting an alkylthiosialic acid derivative represented by the formula [I]: ##STR1## wherein R represents an acyl group and R.sup.1 and R.sup.2 each represents a lower alkyl group with a compound having alcoholic hydroxyl group at a low temperature in a polar solvent having no hydroxyl group in the presence of a Lewis acid selected from the group consisting of methyl triflate, trimethylsilyl triflate and dimethyl(methylthio)sulfonium triflate. The present invention further provides novel compounds.Type: GrantFiled: May 16, 1989Date of Patent: April 3, 1990Assignee: Wako Pure Chemical Industries, Ltd.Inventors: Akira Hasegawa, Makoto Kiso
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Patent number: 4912204Abstract: The present invention provides antitumor fluoro-substituted 4'-demethylepipodophyllotoxin glucosides.Type: GrantFiled: September 6, 1988Date of Patent: March 27, 1990Assignee: Bristol-Myers CompanyInventors: Takeshi Ohnuma, Tetsuro Yamasaki, Hideo Kamei, Takayuki Naito
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Patent number: 4906579Abstract: A method to selectively oxidize a polyglucose, on the oxygen of the hydroxy groups of the C-6 position of the glucose rings, while substantially maintaining the degree of polymerization of the polyglycosidic units, comprising heating a 6-sulfonyl polyglucose, for instance 6-O-para-(P)-toluene sulfonyl polyglucose with dimethyl sulfoxide (DMSO) in the presence of at least a catalytic amount of a catalyst selected from a member of the group consisting of: symmetrical--collidine, sodium bicarbonate and pyridine, to produce a polyglucose having aldehyde groups on the oxygen of the hydroxyl on the C-6 position of the glucose rings. In a preferred embodiment when pyridine is selected, this method enables use of that reaction to obtain other new products having other functional groups, mainly on the C-6 position of the glucose rings, without having to purify the aldehyde which may serve as intermediate.Type: GrantFiled: April 26, 1988Date of Patent: March 6, 1990Assignee: Domtar IncInventors: Manssur Yalpani, Magdy M. Abdel-Malik
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Patent number: 4900816Abstract: There is described a water soluble compound having a molecular weight of from about 70,000 to about 2,000,000 and having the formula I,B--X--(PS)--X--(H) Iin which PS is a polysaccharide of molecular weight from about 2,000 to about 2,000,000,X is a covalently bonded chemical bridging group,H is a group Hb or Hb--ZB is a blocked activating groupHb is a hemoglobin residue, andZ is an oxygen affinity reducing ligand containing two or more phosphate groups.There are also described processes for making the compounds, and their formulations and use as oxygen transporting agents.Type: GrantFiled: May 23, 1988Date of Patent: February 13, 1990Assignee: Fisons plcInventor: Jeffrey T. Wong
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Patent number: 4889843Abstract: The salt formed between the polyanions forming the Trichosaccharide and the NH.sub.2 groups of 2,4-diamino-6-piperidino-pyrimidine-3-oxide represents a novel trichogenic factor by which the activity of the single components is enhanced and the seriously toxic side effects of Minoxidil are done away with.Type: GrantFiled: January 17, 1989Date of Patent: December 26, 1989Assignee: Crinos Industria Farmacobiologica Spa.Inventor: Giovanni Gazzani
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Patent number: 4889928Abstract: Sucrose 6-acylates, key intermediates in the preparation of sucralose, can be prepared by subjecting a sucrose alkyl 4,6-orthoacylate to mild aqueous acidic hydrolysis to provide a mixture of sucrose 4- and 6-acylates and then treating the mixture with a base to convert the 4- acylate to the 6-acylate.The novel sucrose alkyl 4,6-orthoacylates are prepared by reacting sucrose in solution or suspension in an inert organic solvent with a trialkyl orthoacrylate in the presence of an acid catalyst.Type: GrantFiled: March 13, 1989Date of Patent: December 26, 1989Assignee: Tate & Lyle Public Limited CompanyInventor: Philip J. Simpson
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Patent number: 4879282Abstract: New uses for heparin, or heparin-like compounds are described that encompass preserving and healing of cells and cell functions arising from transplantations, circumcisions, dermatitides, fissures, fistulas, stimulation of epithelial growth, keloid prevention, cold injuries, pathology and forensic diagnosis, myocardium, trauma, decubitus ulcers, psoriasis, poisonings, insect and snake bites, corrosive ingestions, the "bends," space-travel sickness, brain and heart nerve conduction electrical dysrhythmias, pulmonary respiratory distress, blood and blood products, ulcerative colon lesions, interstitial cystitis, and related cosmetic uses. The uses are realized by applying the compounds either in solution, or in the form of a cream or aerosol, preferably at a pH of about 5.5, in an effective amount and for a time sufficient to effect treatment. Generally, the concentration of heparin or heparin-like compounds will be in the range of 1500 to 5000 international units per milliliter.Type: GrantFiled: March 17, 1987Date of Patent: November 7, 1989Inventor: Michael J. Saliba, Jr.
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Patent number: 4871776Abstract: A novel fructose analog is disclosed which has been found to modify the food intake of mammals. If administered during the diurnal fasting period, the mammals increase their food intakes. If administered during the diurnal feeding period, food intake is decreased. The compound is 2,5-anhydro-1,6-dihalo-1,6-dideoxy-D-mannitol, preferably 2,5-anhydro-1,6-dichloro-dideoxy-D-mannitol ("Charmitol").Type: GrantFiled: October 22, 1987Date of Patent: October 3, 1989Assignee: Monell Chemical Senses CenterInventors: Michael J. DiNovi, Robert J. Rafka, Mark I. Friedman, Michael G. Tordoff
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Patent number: 4859769Abstract: A second-step virus binding receptor is found in nature on the surface of animal and plant cells. This receptor is thought to be needed for virus penetration into target cells. The second-step receptor has been found to bind a wide variety of viruses belonging to a number of different families. The second-step receptor and natural or synthetic substances which correspond to or are analogous to the binding epitope of the second-step receptor in that they are able to bind to a site on the virus which recognizes the binding epitope of the natural second-step receptor, are therefore indicated for the diagnosis, prophylaxis or treatment of viral infections.Type: GrantFiled: November 5, 1986Date of Patent: August 22, 1989Assignee: Symbicom ABInventors: Karl-Anders Karlsson, Erling Norrby, Goran Wadell
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Patent number: 4855416Abstract: A method for the preparation of dextran sulfate and salts thereof which comprises first forming a complex between sulfur trioxide and formamide at a controlled temperature between 15.degree.-40.degree. C. in the presence of dry nitrogen gas and thereafter reacting said complex with dextran at a controlled temperature between 25.degree.-55.degree. C.Type: GrantFiled: July 20, 1987Date of Patent: August 8, 1989Assignee: Polydex Pharmaceuticals, LtdInventor: Thomas C. Usher
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Patent number: 4847372Abstract: A process for the single-stage preparation of glycosyl fluorides by dissolving saccharides in liquid hydrogen fluoride and evaporating the hydrogen fluoride, wherein the resulting glycosyl fluoride is isolated in such a way that, when the evaporation of the hydrogen fluoride is started at a relatively high temperature, in general at -20.degree. to +20.degree. C., the evaporation is effected at a high evaporation rate or, when a low evaporation rate is used at the start of the evaporation, a sufficiently low temperature is set, in general -80.degree. C. to -30.degree. C.Type: GrantFiled: April 28, 1987Date of Patent: July 11, 1989Assignee: Hoechst AktiengesellschaftInventors: Raimund Franz, Hans M. Deger, Merten Schlingmann
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Patent number: 4826962Abstract: The novel chlorinated sugar O-.alpha.-D-6-chloro-6-deoxygalactopyranosyl-(1.fwdarw.6)-.alpha.-D-4-chlo ro-4-deoxygalactopyranosyl-(1.fwdarw.2)-.beta.-D-1, 6-dichloro-1, 6-dideoxyfructofuranoside (TCR) can be used to prepare sucralose by incubating the TCR in solution in the presence of an enzyme serving to remove the 6-chloro-6-deoxygalactosyl moiety from the 6-position, especially an enzyme derived from a strain of Mortierella vinacea, Circinella muscae or Aspergillus niger. TCR is prepared by treating raffinose with thionyl chloride in the presence of triphenylphosphine oxide.Type: GrantFiled: October 20, 1986Date of Patent: May 2, 1989Assignee: Tate & Lyle Public Limited CompanyInventors: Elner B. Rathbone, Khizar S. Mufti, Riaz A. Khan, Peter S. J. Cheetham, Andrew J. Hacking, Jonathan S. Dordick
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Patent number: 4820692Abstract: Compounds of the formula: ##STR1## wherein R is H, Cl, F, Br, I or R.sub.1 S--, in which R.sub.1 is C.sub.1 -C.sub.10 linear or branched chain alkyl or halogenated linear or branched chain alkyl, andwherein R.sub.2, R.sub.3 and R.sub.4 are the same or different and each is H-- or --OH,with the proviso that at least one of R.sub.2, R.sub.3 and R.sub.4 is hydroxy and the further proviso that when R.sub.2, R.sub.3 and R.sub.4 are all OH, R.sub.1 is other than methyl, are useful in inhibiting the growth of MTR kinase-dependent microorganisms and parasitic protazoans. The compounds wherein R is R.sub.1 S are novel, except those wherein R.sub.1 is methyl or isobutyl when R.sub.2, R.sub.3 and R.sub.4 are all OH.Type: GrantFiled: January 9, 1987Date of Patent: April 11, 1989Assignee: State of Oregon, acting by and through the Oregon State Board of Higher Education, acting for and on behalf of the Oregon Health Sciences University and Oregon State UniversityInventors: Michael K. Riscoe, John H. Fitchen, Adolph J. Ferro
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Patent number: 4816573Abstract: Sea plants containing kappa carrageenan are separated from those containing lambda carrageenan by subjecting a mixture of such plants to preferential hydration of the lambda plants without substantial dissolution of carrageenan, and separating it from the kappa plants by selection based on water content or on properties related to or dependent on water content.Type: GrantFiled: November 25, 1985Date of Patent: March 28, 1989Assignee: Prince Edward Island Development AgencyInventor: R. John Whitaker
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Patent number: 4810695Abstract: Chitosan derivatives in the form of coordinated complexes with ferrous ions in which coordinated bonds are established between the ferrous ion and the amino group and hydroxyl group present respectively in position 2 and position 3 of the chitosanglucosamine ring.Said chitosan derivatives are soluble in an aqueous medium and are able to release iron into the gastrointestinal tract in a controlled manner.Type: GrantFiled: May 12, 1986Date of Patent: March 7, 1989Assignee: Establissement TexcontorInventors: Franco Conti, Vito Marinoni
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Patent number: 4806275Abstract: New anionic derivatives of mono and polyglycosides which are surface-active agents are described which anionic derivatives have the general formula ##STR1## wherein G is a glycosyl moiety which is derived from a reducing sugar selected from the group consisting of fructose, glucose, mannose, galactose, talose, gulose, allose, altrose, idose, arabinose, xylose, lyxose, ribose or mixtures thereof,R is an alkyl group substituted at the reducing carbon of the reducing sugar from which the glycosyl moiety, G, is derived, said alkyl group being straight chain or branched chain having 6 to 30 carbon atoms,x=1 to 10,at least one of the hydroxyl groups of at least one of the glycosyl moieties (or of a hydroxyalkyl group attached directly or indirectly to a hydroxyl group of said glycosyl moiety) has a Z group substituted in place of said hydroxyl group, Z is a substituent which is ##STR2## O(CH.sub.2).sub.p CO.sub.2 M, OSO.sub.3 M, O(CH.sub.2).sub.p So3.sub.m and mixtures thereof andR.sub.1 =(CH.sub.2).sub.2 CO.sub.Type: GrantFiled: August 19, 1987Date of Patent: February 21, 1989Assignee: A. E. Staley Manufacturing CompanyInventors: Donald L. Johnson, Kenneth B. Moser, Vivian Valenty
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Patent number: 4801700Abstract: A process for the preparation of 1,6-dichloro-1,6-dideoxy-.beta.-D-fructofuranosyl-4-chloro-4-deoxy-.alpha. -galactopyranoside comprising the steps of (a) reacting sucrose with a tritylating agent; (b) acetylating the tritylated reaction product; (c) detritylating the acetylated reaction product; (d) isomerizing the resulting penta-acetate; (e) chlorinating the isomerized product; and (f) deacetylating the chlorinated reaction product.Type: GrantFiled: October 20, 1986Date of Patent: January 31, 1989Assignee: McNeilab, Inc.Inventors: William Tully, Nicholas M. Vernon, Peter A. Walsh
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Patent number: 4794178Abstract: Organic compounds labeled with no-carrier-added fluorine 18 are processed yield a compound having a formula in the form of .sup.18 F-R through a nucleophilic substitution reaction. The process has a series of steps. The first step of the process relates to providing an organic compound having a formula of X-R. X is the nucleophilic leaving group in the substitution action, and R is a preferred substituted hydrocarbon structure being selected from aliphatic, alicyclic, heterocyclic aliphatic, carbocyclic and heterocyclic aromatic structures. The X-R compounds with acid hydrogen are excluded. The next step is to bring the organic compound X-R into contact with fluoride ions which are present in a solvent. These fluoride ions are essentially carrier free .sup.18 F ions. The organic compound is brought into contact with the fluoride ions in an apparatus to produce a reaction.Type: GrantFiled: July 5, 1985Date of Patent: December 27, 1988Assignee: Kernforschungsanlage Julich Gesellschaft mit beschrankter HaftungInventors: Heinrich H. Coenen, Kurt Hamacher, Manfred Schuller, Gerhard Stocklin, Bernd Klatte, Arndt Knochel
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Patent number: 4783526Abstract: Chlorination of carbohydrates and alcohols utilizing a chlorinating reagent selected from triphenylphosphine oxide/thionyl chloride, thiphenylphosphine oxide/phosgene, triphenylphosphine sulfide/thionyl chloride and triphenylphosphine sulfide/phosgene.Type: GrantFiled: October 20, 1986Date of Patent: November 8, 1988Assignee: McNeilab, Inc.Inventors: Eleanor A. O'Brien, Thomas O'Connor, Mathew R. J. Tuite, Leroy B. High
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Patent number: 4782141Abstract: This invention relates to salts of primycin formed with an organic acid--preferably a C.sub.1-16 aliphatic carboxylic acid, a halogenated carboxylic acid, an aliphatic dicarboxylic acid, an aromatic carboxylic acid, a substituted aromatic carboxylic acid or an organic sulfonic acid--or an inorganic acid--preferably a hydrohalogenic acid.There is furtheron provided a process for the preparation of new primycin salts which comprises reacting a suspension of primycin sulfate formed with an aliphatic alcohol containing 1-4 carbon atoms with a barium salt.The new primycin salts of the present invention possess excellent antibiotic properties.Type: GrantFiled: July 2, 1985Date of Patent: November 1, 1988Assignee: Chinoin Gyogyszer ES Vegyeszeti Termekek Gyara RT.Inventors: Gyula Dekany, Judit Frank
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Patent number: 4754026Abstract: A process is disclosed for producing a 4-O-sulfonyluracil derivative of the formula ##STR1## [wherein R.sup.1 is hydrogen, halogen, alkyl and alkoxy, R.sup.2 is glycosyl having protected hydroxyls; and --SO.sub.2 R.sup.3 is an organic sulfonyl] which comprises reacting an uracil derivative of the formula ##STR2## [wherein R.sup.1 and R.sup.2 are as defined above] with an organic sulfonylating agent of the formula R.sup.3 SO.sub.2 X [wherein R.sup.3 SO.sub.2 is an organic sulfonyl and X is halogen] in the presence of potassium carbonate. The obtained 4-O-sulfonyluracil is further subjected to amination. The processes are industrially adavantageous and produce cytosine derivatives such as cytidine in high yield.Type: GrantFiled: May 27, 1986Date of Patent: June 28, 1988Assignee: Takeda Chemical Industries, Ltd.Inventors: Mitsuru Kawada, Kiyoharu Matsumoto, Masaaki Tsurushima
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Patent number: 4751294Abstract: Sucralose (4-chloro-4-deoxy-.alpha.-D-galactopyranosyl 1,6-dichloro-1,6-dideoxy-.beta.-D-fructofuranoside) is thermally stabilized by co-crystallization with a nitrogenous base, for example niacinamide or an amino acid.Type: GrantFiled: January 14, 1986Date of Patent: June 14, 1988Assignee: Tate & Lyle Public Limited CompanyInventor: Graham Jackson
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Patent number: RE33509Abstract: Compounds of the general formula (I) are potent sweeteners, especially 4,1',6'-tribromo-4,1',6'-trideoxygalactosucrose: ##STR1## in which R' represents a chlorine or bromine atom;R.sup.2 and R.sup.3 respectively represent a hydroxy group and a hydrogen atom or a hydrogen atom and a chlorine or bromine atom;R.sup.4 represents a chlorine or bromine atom; at least one of R', R.sup.3 and R.sup.4 representing a bromine atom.Type: GrantFiled: May 3, 1989Date of Patent: December 25, 1990Assignee: Tate & Lyle p.l.c.Inventors: Graham Jackson, Michael R. Jenner, Riaz A. Khan