Sulfur Or Halogen Containing Patents (Class 536/122)
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Patent number: 4716225Abstract: A method of metabolically mapping one or more central nervous system components of a mammalian body by computerized axial tomography scanning which entails injecting an effective amount of a 2-, 5- or 6-iodo-substituted hexose, as a contrast medium, into the mammalian body, and scanning the mammalian body by computerized axial tomography, thereby visualizing the concentration flux of said hexose in the central nervous system component or components.Type: GrantFiled: September 30, 1985Date of Patent: December 29, 1987Assignee: Georgetown UniversityInventors: Robert S. Ledley, Douglas M. Gersten
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Patent number: 4696980Abstract: The adsorbent consists of a solid phase, completely or partially penetrated by or surface-coated with a hydrophilic molecular polymer netting to which has been bound substituents or cross bridges having chain sequences of the structureX--CH.sub.2 --CH.sub.2 --SO.sub.2 --CH.sub.2 --CH.sub.2 --S--Ywhere X is ether oxygen, a thioether sulfur atom or a nitrogen atom and Y is a substituted or unsubstituted alkyl, aryl or heteroaromatic group. The solid phase consists of particles with a diameter of less than 1 mm and the molecular polymer netting consisting of a cross-linked polyhydroxy polymer such as a polysaccharide, preferably a polygalactane such as agar or agarose or a cross-linked polyamide, e.g. polyacryl amide. Y can be hydroxy alkyl or mercapto alkyl, or phenyl alkyl or phenyl substituted with halogen or nitro groups. The adsorbent is prepared by first converting in a known manner a hydrophilic polymer containing OH and/or CONH.sub.Type: GrantFiled: April 30, 1985Date of Patent: September 29, 1987Inventor: Jerker Porath
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Patent number: 4661474Abstract: New compounds, 2',3'-dideoxy-2'-fluorokanamycin A and 1-N-(.alpha.-hydroxy-.omega.-aminoalkanoyl) derivatives thereof, particularly 1-N-(DL- or L-3-amino-2-hydroxypropionyl)- and 1-N-(L-4-amino-2-hydroxybutyryl)-2',3'-dideoxy-2'-fluorokanamycins A are now provided, which are each useful as antibacterial agent. 2',3'-Dideoxy-2'-fluorokanamycin A is prepared by a process comprising condensing a 6-azido-4-O-protected-2,3,6-trideoxy-2-fluoro-.alpha.-D-ribo-hexopyranosyl bromide with the 4-hydroxyl group of a 6-O-(2',4',6'-tri-O-protected-3'-N-protected-3'-amino-3'-deoxy-.alpha.-D-g lucopyranosyl)-1,3-bis-N-protected-2-deoxystreptamine, reducing the resulting condensation product to convert its azido group into an amino group, and removing the remaining amino-protecting and hydroxyl-protecting groups from the reduction product.Type: GrantFiled: December 10, 1985Date of Patent: April 28, 1987Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Hamao Umezawa, Sumio Umezawa, Tsutomu Tsuchiya, Yoshiaki Takahashi
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Patent number: 4656159Abstract: Compounds of the formula ##STR1## wherein X is halogen; each R independently represents H, a C.sub.1 -C.sub.4 alkyl group, a C.sub.2 -C.sub.4 alkanoyl group, a phosphate group, or a sulfate, sulfonate, or benzoate group with the proviso that no more than one sulfate, sulfonate, or benzoate group is present in said compound; and R' represents R or a carbohydrate residue derived from a carbohydrate having the formula R'OH with the proviso that R' and the R on C-2 or both R groups on C-3 and C-4 together can represent an isopropylidene group; or a pharmaceutically acceptable salt thereof, are disclosed along with methods of synthesizing and using these compounds.Type: GrantFiled: October 31, 1984Date of Patent: April 7, 1987Assignee: Georgetown UniversityInventors: Eugene McPherson, Philip S. Schein
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Patent number: 4645756Abstract: This invention relates to [.alpha.,.omega.-bis(diphenylphosphino)hydrocarbon]bis[(thiosugar)gold] and bis[(selenosugar)gold] derivatives, pharmaceutical compositions comprising an effective tumor cell growth-inhibiting amount of such a derivative, and a method of treating tumor cells sensitive to such a derivative which comprises administering a tumor cell growth-inhibiting amount of such a derivative to an animal afflicted by said tumor cells.Type: GrantFiled: September 27, 1985Date of Patent: February 24, 1987Assignee: Smith Kline Beckman CorporationInventors: David T. Hill, Randall K. Johnson
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Patent number: 4617386Abstract: Process for the production of 2-deoxy-2-fluoro-D-glucose and the corresponding .sup.18 F-compound in which methyl 4,6-O-benzylidine-3-O-methyl-2-O-trifluoromethanesulfonyl-.beta.-D-mannopy ranoside is reacted with a triflating reagent, the resulting compound reacted with CsHF.sub.2, RbF or the corresponding .sup.18 F-compounds, and thereafter the alkyl groups removed by hydrolysis.Type: GrantFiled: April 25, 1983Date of Patent: October 14, 1986Assignee: The United States of America as represented by the United States Department of EnergyInventors: David R. Elmaleh, Shlomo Levy, Chyng-Yann Shiue, Alfred P. Wolf
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Patent number: 4612373Abstract: Compounds of the general formula: ##STR1## (in which X represents a hydrogen atom or an alkoxy or arylalkoxy group) are new compounds; those where X represents a hydrogen atom or a methoxy group are potent sweeteners while those with a cleavable 6-ether group are key intermediates in the preparation of 4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose (TGS). They are prepared by chlorinating a sucrose 6-ether, by etherifying a suitably protected derivative of TGS or, in the case where X represents hydrogen, by debromination of 6-bromo-4,1',6'-trichloro-4,6,1',6'-tetradeoxygalactosucrose.Type: GrantFiled: September 12, 1983Date of Patent: September 16, 1986Assignee: Tate & Lyle Public Limited Co.Inventors: Riaz A. Khan, Khisar S. Mufti, Gita D. Patel
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Patent number: 4609478Abstract: A sulfonated 1-O substituted glucoside having the formula: ##STR1## wherein: (a) R is substituted or unsubstituted alkyl, aryl or aralkyl,(b) one or both of the R.sub.1 groups is either substituted or unsubstitutedMO.sub.3 S--CH.sub.2 --CH.dbd.CH--CH.sub.2).sub.nwherein M is H, a metal ion or ammonium, andn is an integer from 0 to 18, and(c) any remaining R.sub.1 group is H; useful as an oil recovery agent.Type: GrantFiled: February 21, 1984Date of Patent: September 2, 1986Assignee: Olin CorporationInventor: Philip A. Egan
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Patent number: 4582916Abstract: Sulfamates of the following formula (I): ##STR1## wherein X is O or CH.sub.2 and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are as herein defined have been found to exhibit anticonvulsant activity and are thus useful in the treatment of conditions such as epilepsy. Further, pharmaceutical compositions containing a compound of formula (I) as well as methods for their use and intermediates form part of the present invention.Type: GrantFiled: February 11, 1985Date of Patent: April 15, 1986Assignee: McNeilab, Inc.Inventors: Bruce E. Maryanoff, Joseph F. Gardocki
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Patent number: 4575549Abstract: The process according to the invention provides, for the purification of FDPH.sub.4 -containing solutions, for a double chromatography combined with the molecular filtration.There are thus obtained concentrated and highly pure solutions containing fructose 1,6 diphosphate acid, which are perfectly suitable to be employed for the preparation of FDP and its salts.Type: GrantFiled: December 18, 1984Date of Patent: March 11, 1986Assignee: Biomedica Foscama Industria Chimico-Farmaceutica S.p.A.Inventors: Massimo Diana, Guglielmo M. Bisso
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Patent number: 4562177Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is a hydrogen atom or a hydroxyl group; R.sup.2 is a hydrogen atom or a hydroxyl or methoxyl group; X is a fluorine, chlorine, bromine or iodine atom; one of Y and Y' is a hydrogen atom and the other is a hydrogen atom or a hydroxyl or acyloxy group; R.sup.3 and R.sup.4 are each independently a hydrogen atom, an alkyl group, a halo- or phenyl-substituted alkyl group, an acyl group or a halo- or phenyl-substituted acyl group or R.sup.3 and R.sup.4 together form a polymethylene chain having 4 to 6 carbon atoms, are useful as anti-tumor agents, especially for treating leukemia; in particular these compounds exhibit high antileukemic activity against P388 murine leukemia.Type: GrantFiled: April 22, 1983Date of Patent: December 31, 1985Assignee: The Ohio State University Research FoundationInventors: Derek Horton, Waldemar A. Priebe
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Patent number: 4549013Abstract: A method of sweetening a substance comprises incorporating therein a mono- or poly- chloro, mono- or poly- deoxy sucrose derivative having chlorine atoms in selected combinations of positions 4,6,1'- and 6'- of the sucrose molecule. The compounds are many times sweeter than sucrose and are formulated as ingestible products, such as foodstuffs and beverages; oral compositions, such as toothpaste and chewing gum; or sweetening compositions, such as tablets, for addition to beverages, etc.Type: GrantFiled: December 20, 1983Date of Patent: October 22, 1985Assignee: Chemical BankInventors: Leslie Hough, Shashikant P. Phadnis, Riaz A. Khan, Michael R. Jenner
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Patent number: 4544740Abstract: The invention relates to (E)-5-(2-bromovinyl)-uridine and its derivatives of general formula VI, ##STR1## wherein R.sup.1 stands for a hydrogen atom, C.sub.1-8 alkanoyl group, benzoyl group or a benzoyl group substituted in para position either with a C.sub.1-4 alkyl group or a halogen atom, and a process for preparing them by brominating 2',3',5'-tri-O-acyl-5-ethyl-uridine of general formula IV, ##STR2## wherein R is identical with R.sup.1, except where R.sup.1 stands for a hydrogen atom, dehydrohalogenating the resulting dibromo compound of general formula V ##STR3## and optionally deacylating it. The resulting compounds of general formula VI are exhibiting significant potency against Herpes simplex virus species and are of remarkably low acute toxicity.Type: GrantFiled: September 7, 1982Date of Patent: October 1, 1985Assignee: Egyt Gyogyszervegyeszeti GyarInventors: Anna Szabolcs nee Borbas, Laszlo tvos, Janos Sagi, Attila Szemzo, Maria Peredy nee Kajtar, Istvan Horvath, Istvan Koczka, Csilla Rethati, Pal Ivan, Ildiko Fritzsche nee Lukacs, Janos Nagy
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Patent number: 4542209Abstract: A fluorine-containing uridine derivative of the formula: ##STR1## wherein R is lower acyl, fluorine-containing lower acyl or fluorine-containing lower alkyl; and X is hydrogen or hydroxyl, which is prepared by a process which comprises fluorinating 2', 3'-O-isopropylideneuridine with fluorine in a solvent selected from the group consisting of lower carboxylic acids, fluorine-containing lower carboxylic acids and fluorine-containing lower alcohols, and is converted to a 5-fluorouridine derivative of the formula: ##STR2## wherein R and X are as defined above by reacting the fluorine-containing uridine derivative of the formula (I) with a base in an organic solvent at a temperature of 0.degree. to 80.degree. C.Type: GrantFiled: December 7, 1983Date of Patent: September 17, 1985Assignee: Daikin Kogyo Co., Ltd.Inventors: Takao Takahara, Yorisato Hisanaga
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Patent number: 4524066Abstract: The invention relates to a process for the preparation of an injectable chondroitin polysulfate, which is characterized in thatA crude chondroitin polysulfate is depolymerized oxidatively,B the depolymerized chondroitin polysulfate is bleached, if necessary, with peracetic acid,C the product obtained after A or B is subjected once or twice to precipitation with methanol and/or ultrafiltration for fractionation with respect to molecular weight,D the product obtained after C is demineralized, if necessary, with cation exchangers, andE the product obtained after C or D is decolorized, if necessary, with active charcoal.The invention furthermore relates to a chondroitin polysulfate which can be prepared by the above process. The invention also relates to a chondroitin polysulfate with an acute toxicity (LD.sub.50), on intravenous administration, of >3,500 mg/kg in NMRI mice, of >3,000 mg/kg in Wistar rats, of >1,000 mg/kg in cats and of >1,000 mg/kg in dogs.Type: GrantFiled: April 29, 1982Date of Patent: June 18, 1985Assignee: Luitpold-Werk Chemisch-pharmazeutische FabrikInventor: Karl H. Wolf
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Patent number: 4515782Abstract: Cation salts of substituted phenyl-1-thio(poly-O-sulfo)-.alpha.(or .beta.)-D-glucopyranoside, useful as modulators of the complement system, the intermediates thereof and the process of making such intermediates and end products.Type: GrantFiled: August 29, 1983Date of Patent: May 7, 1985Assignee: American Cyanamid CompanyInventors: Robert E. Schaub, Thomas G. Miner, Seymour Bernstein
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Patent number: 4514562Abstract: Fluorinated derivatives of erythromycins A, B, C and D, having antibiotic activity, are prepared, starting from 8,9-anhydroerythromycin 6,9-hemiacetals or their N-oxides, through the reaction with a compound capable of generating electrophilic reactive fluorine, the resulting reaction product undergoing thereafter a reduction, possibly together with a methylation, to the corresponding (8S)-8-fluoroerythomycins.Type: GrantFiled: November 22, 1982Date of Patent: April 30, 1985Assignee: Pierrel SpaInventor: Luciano Toscano
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Patent number: 4508892Abstract: Conjugates of heavy atoms containing analytes or their analogs and fluorescent molecules are covalently bonded to macromolecular supports to minimize the interference of fluorescence during assays, due to non-specific binding of serum proteins to the conjugate.Type: GrantFiled: August 25, 1982Date of Patent: April 2, 1985Assignee: Syva CompanyInventor: Robert A. Yoshida
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Patent number: 4495170Abstract: Synergized compositions contain a mixture of different sweetening agents, at least one of which is saccharin, stevioside, acesulpham K or other sweetening agent with an associated bitter taste, and at least another of which is a chlorodeoxysucrose, chlorodeoxygalactosucrose or other sweetening agent which is a chlorodeoxysugar.Type: GrantFiled: April 22, 1982Date of Patent: January 22, 1985Assignee: Tate & Lyle Public Limited CompanyInventors: Pamela K. Beyts, Zdenek Latymer
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Patent number: 4477443Abstract: Tylosin compounds of the formula ##STR1## wherein R.sub.1 represents a hydroxyl group; a halogen atom; ##STR2## group (wherein R.sub.5 is a hydrogen atom or a lower alkyl group which may be substituted by a hydroxyl group and R.sub.6 is a hydrogen atom, a lower alkyl group which may be substituted by a hydroxyl group, an aryl group, an aralkyl group, a cycloalkyl group having 3-10 carbon atoms, --CO(O).sub.m --R.sub.7 group (wherein m is 0 or 1 and R.sub.7 is a lower alkyl group, an aryl group, an aralkyl group, a furanyl group, or a pyridyl group), or --CH.sub.2 --R.sub.13 group (wherein R.sub.13 is a mono-, di-, or trifluoromethyl group)); --N(CH.sub.2).sub.n group (wherein n is an integer of 2-15) which may be substituted by an oxo group, a hydroxyl group, a lower alkyl group, or a hydroxy lower alkyl group; an imidazolyl group, a morpholino group, or a piperazino group each may be substituted by a lower alkyl group; or --OOCCH.sub.2 --R.sub.8 group (wherein R.sub.8 is ##STR3## group (wherein R.sub.Type: GrantFiled: July 6, 1982Date of Patent: October 16, 1984Assignee: Zaidan Hojin Biselbutsu Kagaku Kenkyu Kai (Microbial Chemistry Research Foundation)Inventors: Hamao Umezawa, Sumio Umezawa, Tsutomu Tsuchiya, Tomio Takeuchi, Akihiro Tanaka, Hidenori Iwamoto, Shuichi Sakamoto
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Patent number: 4473546Abstract: 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 18, 1982Date of Patent: September 25, 1984Assignee: Tate & Lyle Public Limited CompanyInventors: Graham Jackson, Michael R. Jenner, Riaz A. Khan
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Patent number: 4470976Abstract: Poly-cation salts of 4-O-polyhexaose-thio-arylene sulfate derivatives, useful as modulators of the complement system, the intermediates thereof and the process of making such intermediates and products.Type: GrantFiled: August 29, 1983Date of Patent: September 11, 1984Assignee: American Cyanamid CompanyInventors: Thomas G. Miner, Robert E. Schaub, Seymour Bernstein
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Patent number: 4468385Abstract: Poly-cation salts of 4-O-polyhexaose-thio-alkylene sulfate derivatives, useful as modulators of the complement system, the intermediates thereof and the process of making such intermediates and products.Type: GrantFiled: August 29, 1983Date of Patent: August 28, 1984Assignee: American Cyanamid CompanyInventors: Francis M. Callahan, Thomas G. Miner, Seymour Bernstein
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Patent number: 4443486Abstract: A stabilizer for milk products comprised of a carrageenan extractive of Eucheuma cottonii seaweed having a water viscosity at 1.5% concentration and 75.degree. C. of not less than 5 mPa.s and not more than about 20 mPa.s.Type: GrantFiled: March 11, 1981Date of Patent: April 17, 1984Assignee: FMC CorporationInventor: Kenneth B. Guiseley
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Patent number: 4440758Abstract: Poly-cation salts of bis(or tris)[4-O-monohexose-oxy]-arylene sulfate derivatives useful as modulators of the complement system, the intermediates thereof and the process of making such intermediates and products.Type: GrantFiled: October 25, 1982Date of Patent: April 3, 1984Assignee: American Cyanamid CompanyInventors: Janis Upeslacis, Robert E. Schaub, Seymour Bernstein
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Patent number: 4435387Abstract: Poly-cation salts of bis (or tris) 4-O-polyhexose-thio-arylene sulfate derivatives, useful as modulators of the complement system, the intermediates thereof and the process of making such intermediates and end products.Type: GrantFiled: October 25, 1982Date of Patent: March 6, 1984Assignee: American Cyanamid CompanyInventors: Robert E. Schaub, Janis Upeslacis, Seymour Bernstein
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Patent number: 4435440Abstract: A method of sweetening a substance comprises incorporating therein a mono- or poly- chloro, mono- or poly- deoxy sucrose derivative having chlorine atoms in selected combinations of positions 4,6,1'- and 6'- of the sucrose molecule. The compounds are many times sweeter than sucrose and are formulated as ingestible products, such as foodstuffs and beverages; oral compositions, such as toothpaste and chewing gum; or sweetening compositions, such as tablets, for addition to beverages, etc.Type: GrantFiled: December 30, 1976Date of Patent: March 6, 1984Assignee: Tate & Lyle LimitedInventors: Leslie Hough, Shashikant P. Phadnis, Riaz A. Khan, Michael R. Jenner
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Patent number: 4431636Abstract: Poly-cation salts of bis (4-O-polyhexaose-thio)-phenyl urea sulfate derivatives, useful as modulators of the complement system, the intermediates thereof and the process of making such intermediates and end products.Type: GrantFiled: May 24, 1982Date of Patent: February 14, 1984Assignee: American Cyanamid CompanyInventors: Robert E. Schaub, Janis Upeslacis, Seymour Bernstein
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Patent number: 4431637Abstract: Poly-cation salts of bis (or tris) [4-O-polyhexose-oxy]-arylene sulfate derivatives useful as modulators of the complement system, the intermediates thereof and the process of making such intermediates and end products.Type: GrantFiled: October 25, 1982Date of Patent: February 14, 1984Assignee: American Cyanamid CompanyInventors: Janis Upeslacis, Robert E. Schaub, Seymour Bernstein
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Patent number: 4431638Abstract: Poly-cation salts of bis(or tris)[4-O-monohexose-thio]-arylene sulfate derivatives useful as modulators of the complement system, the intermediates thereof and the process of making such intermediates and end products.Type: GrantFiled: October 25, 1982Date of Patent: February 14, 1984Assignee: American Cyanamid CompanyInventors: Robert E. Schaub, Janis Upeslacis, Seymour Bernstein
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Patent number: 4407796Abstract: Poly-cation salts of bis-(or tris-) [polyhexaose-thio (or sulfinyl, or sulfonyl)]-arylene sulfate derivatives, useful as modulators of the complement system, the intermediates thereof and the process of making such intermediates and end products.Type: GrantFiled: December 28, 1981Date of Patent: October 4, 1983Assignee: American Cyanamid CompanyInventors: Thomas G. Miner, Seymour Bernstein
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Patent number: 4405654Abstract: Compounds of the general formula (I) ##STR1## (wherein X represents a halogen atom; R.sup.1 and R.sup.2 respectively represent a combination selected from the group consisting of: a hydroxy group and a hydrogen atom; a halogen atom and a hydrogen atom; and a hydrogen atom and a halogen atom; andR.sup.3 and R.sup.4, which may be the same or different, each represent a substituent selected from the group consisting of a halogen atom and a hydroxy group;at least one of R.sup.1, R.sup.2 and R.sup.3 representing a halogen atom) are potent sweeteners obtainable by opening a corresponding 3',4'-lyxoepoxide with a source of halide ions.Type: GrantFiled: April 26, 1982Date of Patent: September 20, 1983Assignee: Tate & Lyle Public Limited CompanyInventor: Cheang K. Lee
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Patent number: 4401811Abstract: An inexpensive cation exchanger useful in purifying waste water is produced by treating comminuted bark in separate steps with an alkali hydroxide solution of at least 5% by weight, preferably 20-40% by weight, and with 30-75% by weight sulphuric acid, preferably 50-65% by weight. After each step washing with water is performed until the pH-value after the alkali hydroxide treatment goes below 9 and after the sulphuric acid treatment goes above 3. Preferably, the treatment with alkali hydroxide precedes the treatment with sulphuric acid. The treatment with alkali hydroxide is carried out for 0.5-20 hours, preferably 3-10 hours, and the treatment with sulphuric acid is carried out from 0.5-8 hours, preferably from 1-6 hours. The cation exchanger can be regenerated with alkali hydroxide solution, particularly sodium hydroxide solution.Type: GrantFiled: December 14, 1981Date of Patent: August 30, 1983Inventor: Sven E. Jorgensen
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Patent number: 4393052Abstract: Novel antitumor anthracycline glycosides are prepared by condensing daunomycinone with 2,3,4,6-tetradeoxy-4-C-methylene-3-trifluoroacetamido-L-threo-hexopyranosy l chloride; 2,3,4,6-tetradeoxy-4-C-methylene-3-trifluoroacetamido-L-arabino-hexopyrano syl chloride or 2,3,6-trideoxy-4-C-trifluoroacetamidomethyl-3-trifluoroacetamido-3-O-trifl uoroacetyl-L-lyxo-hexopyranosyl chloride.Type: GrantFiled: October 29, 1981Date of Patent: July 12, 1983Assignee: Farmitalia Carlo Erba S.p.A.Inventors: Alberto Bargiotti, Giuseppe Cassinelli, Sergio Penco, Federico Arcamone, Annamaria Casazza
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Patent number: 4389523Abstract: A cellulose sulfate salt having a heparinic action is provided, which satisfies requirements of 0.8.ltoreq.<<F>>.ltoreq.2.6, <<f.sub.2 >>.gtoreq.<<f.sub.3 >> and <<f.sub.2 >>.gtoreq.<<f.sub.6 >> wherein <<f.sub.2 >>, <<f.sub.3 >> and <<f.sub.6 >> stand for probability of substitution of atoms H in the OH groups bonded to the C.sub.2, C.sub.3 and C.sub.6 positions of the glucopyranose ring unit by sulfuric acid radicals, respectively, and <<F>> stands for the total substitution degree which is the sum of <<f.sub.2 >>, <<f.sub.3 >> and <<f.sub.6 >>. The cellulose sulfate salt is prepared by reacting a cellulose having a crystal form I with an SO.sub.3 /amine or SO.sub.3 /amide complex in an amount of 2 to 4 mole equivalents per glucose unit of the cellulose at -10.degree. C. to 40.degree. C.Type: GrantFiled: November 25, 1981Date of Patent: June 21, 1983Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Kunihiko Okajima, Kenji Kamide, Toshihiko Matsui
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Patent number: 4384998Abstract: Disclosed is a chiral, total synthesis of thienamycin from D-glucose which proceeds via intermediates I, II and III to known aldehyde IV which is known to be useful in the total synthesis of thienamycin (V): ##STR1## wherein: R is lower alkyl having 1-6 carbon atoms or bi-valent alkyl having 2-6 carbon atoms which joins the two sulfur atoms; R.sup.1 is lower alkyl or aralkyl, such as benzyl and the like; and R.sup.2 is hydrogen or a removable protecting group, such as triorganosilyl wherein the organo groups are independently selected from lower alkyl, phenyl and phenylloweralkyl.Type: GrantFiled: March 30, 1981Date of Patent: May 24, 1983Assignee: Merck & Co., Inc.Inventor: Philippe L. Durette
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Patent number: 4380476Abstract: A process for the preparation of 4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose (TGS) comprising the steps of:(a) reacting sucrose with an acylating reagent under conditions to provide a mixture of acylated sucrose derivatives containing a major proportion of 6-monoacylated material;(b) optionally separating 6-monoacylated sucrose derivative from other acylated derivatives before step (c);(c) reacting the monoacylated sucrose derivative with a chlorinating reagent capable of chlorinating at positions 1', 4 and 6' of a sucrose 6- acylate; and(d) deacylating and separating (in either order) the 4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose material formed.Type: GrantFiled: June 19, 1981Date of Patent: April 19, 1983Assignee: Talres Development (N.A.) N.V.Inventors: Khizar S. Mufti, Riaz A. Khan
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Patent number: 4366149Abstract: Novel antitumor anthracycline glycosides are prepared by condensing daunomycinone with 2,3,4,6-tetradeoxy-3,4-ditrifluoroacetamido-L-lyxo-[or L-arabino-]hexopyranosyl chloride.Type: GrantFiled: October 29, 1981Date of Patent: December 28, 1982Inventors: Alberto Bargiotti, Giuseppe Cassinelli, Sergio Penco, Federico Arcamone, Annamaria Casazza
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Patent number: 4362869Abstract: 4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose is prepared by a process including the steps of:(a) isomerizing 2,3,4,3',4'-penta-O-acetyl sucrose to 2,3,6,3',4'-penta-O-acetyl sucrose;(b) chlorinating the isomerized acetate at the 4,1' and 6'-positions; and(c) deacetylating the resulting chlorinated product; the isomerization step (a) being effected by treating a solution of 2,3,4,3',4'-penta-O-acetyl sucrose in an inert solvent with a weak acid at an elevated temperature.Type: GrantFiled: December 4, 1980Date of Patent: December 7, 1982Assignee: Talres Development (N.A.) N.V.Inventors: Michael R. Jenner, David Waite, Graham Jackson, John C. Williams
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Patent number: 4362720Abstract: O-acetylated glycals react with ceric ammonium nitrate in the presence of sodium azide to provide, in good yield, O-acetylated 2-azido-2-deoxy glycosyl nitrates. These nitrates can be used to prepare 2-amino-2-deoxy sugars, such as D-galactosamine and lactosamine. The O-acetylated 2-azido-2-deoxy glycosyl nitrates can alternately be converted to O-acetylated 2-azido-2-deoxy glycosyl halides which are useful in the preparation of O-acetylated 2-azido-2-deoxy glycosides, which in turn can be reduced to 2-amino-2-deoxy glycosides. Of particular interest are the syntheses of 2-amino-2-deoxy glycosides which correspond to the terminal units of the antigenic determinant for the human A blood group. Attachment of these glycosides to a solid support provides immunoabsorbents which efficiently and preferentially absorb anti-A antibodies from blood plasma.Type: GrantFiled: September 19, 1979Date of Patent: December 7, 1982Assignee: Chembiomed Ltd.Inventors: Raymond U. Lemieux, R. Murray Ratcliffe
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Patent number: 4359461Abstract: Mono-, di- and tri-adamantylcarbonyl- digalactopyranosyl- glucopyranosyl- fructofuranose sulfate salts, useful as complement inhibitors and the process of making such compounds.Type: GrantFiled: October 28, 1981Date of Patent: November 16, 1982Assignee: American Cyanamid CompanyInventors: Vijay G. Nair, Seymour Bernstein
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Patent number: 4359460Abstract: 6'-(1-Adamantanecarboxylate)-6-O-.alpha.-D-galactopyranosyl-.alpha.-D-gluco pyranose sulfate salts, useful as complement inhibitors, and the process for making such compounds.Type: GrantFiled: October 13, 1981Date of Patent: November 16, 1982Assignee: American Cyanamid CompanyInventors: Vijay G. Nair, Seymour Bernstein
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Patent number: 4357326Abstract: O-.alpha.-D-glucopyranosyl(1.fwdarw.4)-[O-.alpha.-D-glucopyranosyl-(1.fwdar w.4)].sub.n -O-.beta.-D-glucopyranosyl(1.fwdarw.6)-.beta.-D-fructofuranosyl-O-.alpha.- D-galactopyranosyl(1.fwdarw.6)-.alpha.-D-glucopyranoside sulfate salts, useful as inhibitors of the complement system and the process of making such compounds.Type: GrantFiled: August 28, 1981Date of Patent: November 2, 1982Assignee: American Cyanamid CompanyInventors: Vijay G. Nair, Joseph P. Joseph, Seymour Bernstein
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Patent number: 4345933Abstract: This invention discloses the compound sucrose tri(2-methoxy-3,6-dichlorobenzoate) and its use in a method of increasing the recoverable sugar in sugar cane.Type: GrantFiled: March 25, 1981Date of Patent: August 24, 1982Assignee: Velsicol Chemical CorporationInventor: George F. Luteri
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Patent number: 4343934Abstract: Crystalline 4,1',6'-trichloro-4,1',6'-trideoxy-galactosucrose exists as the orthorhombic anhydrous form and as the pentahydrate, both of which are more stable than amorphous TGS. Crystals are obtained from seeded aqueous solutions, above 38.degree. C. for the anhydrate; below 38.degree. C. for the pentahydrate.Type: GrantFiled: December 4, 1980Date of Patent: August 10, 1982Assignee: Talres Development (N.A.) N.V.Inventors: Michael R. Jenner, David Waite
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Patent number: 4337249Abstract: N-(4-O-.alpha.-D-glucopyranosyl-.beta.-D-glucopyranosyl)-3,4-dihydroxycinna mamide, nonakis (H-sulfate) (nonaester), nona-alkali metal or alkaline earth metal-salts, useful as modulators of the complement system, the intermediates thereof and the process of making such salts and intermediates.Type: GrantFiled: August 3, 1981Date of Patent: June 29, 1982Assignee: American Cyanamid CompanyInventors: Ransom B. Conrow, Seymour Bernstein
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Patent number: 4335100Abstract: Dextransucrase synthesis of dextran from sucrose is inhibited by substituted sucrose compounds which have an inhibiting group bonded to the 5-position ring carbon. Oral compositions containing such substituted sucrose compounds can be used to control dextran formation in the mouth, and dextran comprises the principal component of dental plaque.Type: GrantFiled: August 6, 1980Date of Patent: June 15, 1982Assignee: Iowa State University Research Foundation, Inc.Inventors: John F. Robyt, John N. Zikopoulos
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Patent number: 4334058Abstract: Rutin poly(H--)sulfate and salts thereof useful as complement inhibitors.Type: GrantFiled: August 25, 1980Date of Patent: June 8, 1982Assignee: American Cyanamid CompanyInventors: Vijay G. Nair, Seymour Bernstein
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Patent number: 4324888Abstract: A process for the preparation of a chlorodeoxy derivative of a reducing aldose having a primary hydroxy group in an exocyclic -CH.sub.2 OH group, in which the said primary hydroxy group is replaced by a chlorine atom to give a chlorodeoxy reducing sugar with a free anomeric center, characterized in that the free reducing sugar is reacted with a reagent comprising an N,N-dialkyl (methaniminium) chloride obtained by reacting an N,N-dialkyl formamide with a chlorinating agent.Type: GrantFiled: March 5, 1980Date of Patent: April 13, 1982Assignee: Talres Development (N.A.) N.V.Inventor: Elner B. Rathbone
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Patent number: H74Abstract: Process for the production of 2-deoxy-2-fluoro-D-glucose and the corresponding .sup.18 F-compound by the reaction of acetyl hypofluorite or the corresponding .sup.18 F-compound with 3,4,6-tri-O-acetyl-D-glucal followed by hydrolysis. Process includes the production of the hypofluorite compound at ambient temperature.Type: GrantFiled: February 24, 1983Date of Patent: June 3, 1986Assignee: The United States of America as represented by The United States Department of EnergyInventors: Chyng-Yann Shiue, Piero A. Salvadori, Alfred P. Wolf, Joanna S. Fowler, Robert R. MacGregor