Mixed Carboxylate Esters Patents (Class 536/64)
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Patent number: 7413662Abstract: A modified sorptive lignocellulosic fibre material with hydroxyl groups on the lignocellulosic fibres doubly modified by esterification with a combination of monocarboxylic and dicarboxylic acid ester groups. A process for the preparation of the sorptive material. The sorptive fibre material is effective for the removal of oils and other contaminants including heavy metals from a fluid such as contaminated water by a combined sorption of hydrophobic contaminants and ion exchange.Type: GrantFiled: December 20, 2005Date of Patent: August 19, 2008Assignee: Danish Plant Fibre Technologies Holding A/SInventors: Per Berre Eriksen, John Mark Lawther, Peter Larsen
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Patent number: 7189464Abstract: In a multi-layer structure of a cellulose acylate film, the averaged degree of acylation of surface layers is controlled in the range of 0.5 to 2.8 by mixing several sorts of cellulose acylates having different averaged degrees of acyation. One of the surface layers is formed on a substrate by casting a solution containing cellulose acylate made of cotton linter. Lubricant particles are added to a solution for the surface layers, and emission compounds to a solution for the inner layers. The obtained cellulose acylate film is excellent in adhesive property to the hydrophobic material without saponification, and adequately used for the polarizing filter, an optical compensation sheet, and liquid crystal display.Type: GrantFiled: March 4, 2004Date of Patent: March 13, 2007Assignee: Fuji Photo Film Co., Ltd.Inventor: Masaru Sugiura
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Patent number: 7122660Abstract: Using the dope containing the following cellulose acetate (1), (2), or (3), a film is prepared by the casting process: (1) a cellulose acetate having carboxyl groups binding to at least one member selected from the group consisting of a cellulose acetate and a hemicellulose acetate, wherein at least a part of said carboxyl groups are in an acidic form; (2) a cellulose acetate containing at least one member selected from the group consisting of an acid having an acid dissociation exponent pKa of 1.93 to 4.50 in water, an alkali metal salt of said acid and an alkaline earth metal of said acid; or (3) a cellulose acetate containing an alkali metal or an alkaline earth metal wherein the total content of an alkaline metal and an alkaline earth metal in 1 gram of the cellulose acetate is from an effective amount to 5.5×10?6 equivalent (in terms of ion equivalent). The above cellulose acetate is also useful for spinning process. The cellulose acetate includes a cellulose diacetate and a cellulose triacetate.Type: GrantFiled: September 3, 1998Date of Patent: October 17, 2006Assignee: Daicel Chemical Industries, Ltd.Inventors: Yukiko Nakanishi, Hiroki Taniguchi, Katako Ueda
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Patent number: 6897303Abstract: A cellulose acetate film is produced from a solution of a cellulose acylate in a mixed solvent. The mixed solvent comprises a main solvent and an alcohol. The mixed solvent essentially does not contain chlorine atom. The main solvent comprises an ester and a ketone. The ester has a solubility parameter of 16 to 23. The ketone has a solubility parameter of 16 to 23. The alcohol has a solubility parameter of 20 to 30. The mixed solvent comprises the ester in an amount of 58 to 96 wt. %, the ketone in an amount of 2 to 15 wt. %, and the alcohol in an amount of 2 to 40 wt. %.Type: GrantFiled: March 20, 2003Date of Patent: May 24, 2005Assignee: Fuji Photo Film Co., Ltd.Inventor: Tsukasa Yamada
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Patent number: 6730374Abstract: Disclosed is a triacetyl cellulose film comprising (a) a triphenyl monophosphate compound and (b) an aromatic polyol-bridged polyphosphate compound. Such a film exhibits a reduced rate of water vapor transmission.Type: GrantFiled: December 13, 2001Date of Patent: May 4, 2004Assignee: Eastman Kodak CompanyInventors: William J. Gamble, Joseph L. Lippert
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Patent number: 6712896Abstract: A cellulose ester film comprises (a) an ultraviolet absorbent polymer having at least one of repeating units represented by formulae (1) and (2) and repeating units having ultraviolet absorbent structures represented by formulae (3), (4) and (5), (b) an ultraviolet absorbent polymer which is a copolymer of a repeating unit represented by the following formula (6), (7) or (19) with a monomer unit derived from another ethylenically unsaturated monomer, (c) an ultraviolet absorbent polymer which is a copolymer of a monomer represented by formula (8) with a monomer represented by formula (9), or (d) modified cellulose in which an ultraviolet absorbent structure bonds directly or through a spacer to a hydroxy group of cellulose or its derivative.Type: GrantFiled: May 8, 2001Date of Patent: March 30, 2004Assignee: Konica Minolta Holdings, Inc.Inventors: Kaori Ono, Isamu Michihata, Osamu Ishige
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Publication number: 20030207407Abstract: The invention provides a method of obtaining a cellulose material from corn fiber wherein the method comprises the steps of: (a) heating a mixture of corn fiber and a liquid; (b) contacting the mixture of step (a) with a protease enzyme, thereby providing a proteolyzed corn fiber and a liquid; (c) separating the liquid from the proteolyzed corn fiber; (d) contacting the proteolyzed corn fiber at least once with an alkaline extractant, thereby providing an insoluble cellulose material and a first liquid comprising arabinoxylan; (e) separating the insoluble cellulose material from the first liquid comprising arabinoxylan at a temperature of at or above about 60° C.; and (f) rinsing the insoluble cellulose material to remove essentially all alkali, thereby providing a cellulose material having a cellulose content of at least about 50% and consisting essentially of cellulose I. Cellulose esters and ethers are also prepared from the derivatizable cellulose prepared according to the methods herein.Type: ApplicationFiled: December 19, 2002Publication date: November 6, 2003Applicant: Eastman Chemical CompanyInventors: Charles M. Buchanan, Norma L. Buchanan, John S. Debenham, Michael C. Shelton, Matthew D. Wood
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Publication number: 20030199687Abstract: The present invention relates to fluorinated biopolymer and polymer derivatives useful as imaging probes, diagnostic agents and contrast agents and to imaging methods employing the fluorinated biopolymers and polymers.Type: ApplicationFiled: April 11, 2003Publication date: October 23, 2003Inventor: Manssur Yalpani
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Publication number: 20020162483Abstract: A cellulose ester film and its manufacturing method are disclosed, the cellulose ester film comprising a compound represented by the following formula (1) in an amount of from 1 to 30% by weight, 1Type: ApplicationFiled: February 14, 2002Publication date: November 7, 2002Inventors: Kunio Shimizu, Takashi Murakami, Toru Kobayashi
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Patent number: 6407224Abstract: A catalytic system for cellulose acylation includes an adduct of sulfuric acid with N,N-dimethylacetamide, free sulfuric acid or free N,N-dimethylacetamide with the following mole ratio of the components: adduct:1.0; free sulfuric acid, max:0.49; or free N,N-dimethylacetamide, max:0.4. A process for producing such a catalytic system is based upon reacting sulfuric acid with N,N-dimethylacetamide in an anhydrous medium at a temperature of 0° C.-25° C. with the following mole weight ratio of the components: sulfuric acid:1.0; N,N-dimethylacetamide, max:1.4. A process for cellulose acylation in the presence of this catalytic system incorporates cellulose treatment with acetic acid followed by treatment of the resultant activated cellulose with a lower fatty acid anhydride at a temperature of 10° C.-90° C. in the presence of this catalytic system taken in an amount of 1.5-30.0 wt.Type: GrantFiled: July 16, 1999Date of Patent: June 18, 2002Assignee: Nauchno-prozvodstvennaya firma “Efiry Tselljulosy”Inventors: Dmitry Petrovich Mironov, Anatoly Ivanovich Shamolin, Eduard Pavlovich Grishin, Valentin Ananievich Bondar
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Patent number: 6211358Abstract: A method for preparing a solution of cellulose acylate is disclosed. The method comprises comprising the steps of (1) chilling an organic solvent containing no chlorinated organic solvent at a temperature of from −100° C. to −10° C., (2) mixing cellulose acylate containing an alkali-earth metal compound in an amount of from 10 ppm to 100 ppm with said chilled organic solvent to form a mixture, (3) swelling the cellulose acylate in the mixture, and (4) dissolving the mixture containing the swollen cellulose acylate by heating.Type: GrantFiled: April 23, 1999Date of Patent: April 3, 2001Assignee: Konica CorporationInventors: Makoto Honda, Takatoshi Yajima
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Patent number: 6184373Abstract: A method for producing an organic cellulose derivative fibrillated fiber includes the steps of mixing a cellulose ester containing stream and a coagulant stream in a first zone of relatively moderate turbulence to produce a slurry containing cellulose ester fibers, passing the slurry containing cellulose ester fibers to a second zone having relatively low turbulence for a sufficient time to increase the hardness of the cellulose ester fiber; and passing the cellulose derivative fibers through a third zone having relatively high shear to produce a fibrillated fiber having a diameter of about 0.5 to about 50 microns and a degree of fibrillation greater than about 6.Type: GrantFiled: September 3, 1999Date of Patent: February 6, 2001Assignee: Eastman Chemical CompanyInventors: Bobby Lynn Bernard, Max Ray Davis
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Patent number: 6160102Abstract: The present invention refers to conjugates formed by a natural or modified oligonucleotide, capable of forming a triple helix with a DNA chain, linked to the aglycone moiety of an anthracycline or to an anthracyclinone via an appropriated linker; such conjugates are capable to bind selectively to specific DNA regions inhibiting their transcription and therefore the formation of the corresponding codified protein.Type: GrantFiled: September 9, 1998Date of Patent: December 12, 2000Assignee: Consiglio Nazionale Delle RicercheInventors: Anna Maria Garbesi, Stefania Bonazzi, Stefania Zanella, Massimo Luigi Capobianco, Giuseppe Giannini, Federico Arcamone
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Patent number: 6160111Abstract: The present invention relates to a process for preparing cellulose esters having a total DS/AGU of 0.1 to 3.0, said process comprising contacting the following:(i) a cellulose material,(ii) a solubilizing amount of a solvent system comprising a carboxamide diluent or a urea-based diluent,(iii) an acylating reagent, and(iv) an insoluble sulfonic acid resin catalyst.Type: GrantFiled: December 2, 1996Date of Patent: December 12, 2000Assignee: Eastman Chemical CompanyInventor: Kevin J. Edgar
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Patent number: 6107285Abstract: According to the invention there is provided a sterile, pyrogen-free, ready-to-use solution of an anthracycline glycoside, especially doxorubicin, which consists essentially of a physiologically acceptable salt of an anthracycline glycoside dissolved in a physiologically acceptable solvent therefor, which has not been reconstituted from a lyophilizate and which has a pH of from 2.5 to 6.5. The solution of the invention is particularly advantageous for the administration by injection of the anthracycline glycoside drugs, e.g. doxorubicin, in the treatment of both human and animal tumors.Type: GrantFiled: January 29, 1992Date of Patent: August 22, 2000Assignee: Pharmacia & UpJohn CompanyInventors: Gaetano Gatti, Diego Oldani, Giuseppe Bottoni, Carlo Confalonieri, Luciano Gambini, Roberto De Ponti
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Patent number: 6103700Abstract: Compounds of formula (A), wherein R.sub.1, R.sub.2, R.sub.3, Y and Z are organic substituents, are useful in the diagnosis of amyloidosis; some of the compounds of formula (A) are novel. Processes for their preparation, and pharmaceutical compositions containing them are also described.Type: GrantFiled: December 24, 1998Date of Patent: August 15, 2000Assignee: Pharmacia & Upjohn S.p.A.Inventors: Tiziano Bandiera, Daniele Fancelli, Michele Caruso, Jacqueline Lansen, Antonino Suarato
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Patent number: 6080396Abstract: A dimer, trimer or tetramer of an anthracycline compound which can be obtained by directly, chemically bonding anthracycline compounds having anticancer activities to each other by an alkali treatment. A high molecular block copolymer-drug complex pharmaceutical preparation in which the high molecular block copolymer having a hydrophilic polymer segment and a hydrophobic polymer segment forms a micelle having the hydrophilic segment as its outer shell and contains in its hydrophobic inner core a dimer, trimer or tetramer of anthracycline compound alone or together with other drugs.Type: GrantFiled: August 18, 1997Date of Patent: June 27, 2000Assignees: Japan Science and Technology Corporation, Yasuhisa Sakurai, Nippon Kayaku Kabushiki KaishaInventors: Masayuki Yokoyama, Kazunori Kataoka, Teruo Okano, Yasuhisa Sakurai, Shigeto Fukushima, Ryuji Uehara, Tomoko Akutsu, Kazuya Okamoto, Hiroko Mashiba, Megumi Machida, Kazuhisa Shimizu
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Patent number: 6075135Abstract: 7-O-(4-Amino-2,4,6-trideoxy-2-fluoro-.alpha.-L-mannopyranosyl)-daunomycinon e or -adriamycinone is now synthesized as a daunomycinone or adriamycinone derivative having the general formula ##STR1## wherein R is a hydrogen atom or hydroxyl group. These novel compounds according to this invention exhibit excellent antitumor activities and have a high solubility in water, and hence they are useful as an antitumor agent.Type: GrantFiled: March 31, 1999Date of Patent: June 13, 2000Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Tomio Takeuchi, Sumio Umezawa, Tsutomu Tsuchiya, Yasushi Takagi
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Patent number: 6020315Abstract: A preparation having increased in vivo tolerability comprising a glycosyl-Y[--C(.dbd.Y)--X--].sub.p --W(R).sub.n --X--C(.dbd.Y)-active compound, sugar or sugar alcohol and, optionally divalent ions, and a pharmaceutically tolerable carrier.Type: GrantFiled: May 13, 1998Date of Patent: February 1, 2000Assignee: Hoechst AktiengesellschaftInventors: Klaus Bosslet, Jorg Czech, Manfred Gerken, Rainer Straub, Matthias Blumrich
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Patent number: 6020316Abstract: Clinical utility of chemotherapy agents is limited by dose-dependent systemic toxicity and emergence of resistant tumor cell lines. The present invention provides derivatives of chemotherapeutic agents which can overcome these limitations. Reaction of a parent drug with glutaraldehyde in aqueous solution followed by ethanolamine yields a product which exhibits enhanced antitumor cytotoxicity and overcomes resistance developed against the parent drug. The derivative compounds of the invention achieve therapeutic effects comparable to those of the parent drugs but at much lower doses, thereby reducing undesirable toxic side effects. The most preferred derivative is glutaraldehyde-modified doxorubicin. Most preferred are methods of treatment for subjects suffering from cancer which comprise administration of glutaraldehyde-modified doxorubicin.Type: GrantFiled: September 25, 1998Date of Patent: February 1, 2000Inventor: Karl W. Lanks
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Patent number: 6011008Abstract: A method for producing a water-soluble polysaccharide conjugate of an oxidation-sensitive substance is described. The method comprises the following steps: (a) activating the polysaccharide to a dialdehyde by periodate oxidation; (b) purifying the dialdehyde from interfering anions and by-products; and (c) coupling the substance to the purified dialdehyde by Schiff base formation to form the conjugate. Optionally, the conjugate of step (c) is reduced to an amine conjugate by a reducing substance. The product conjugate may then be further purified from various reaction byproducts. The disclosed method results in the substance substantially retaining its biological activity. Also described are imine and amine polysaccaride conjugates of various drugs and polypeptides.Type: GrantFiled: June 4, 1998Date of Patent: January 4, 2000Assignee: Yissum Research Developement Company Of The Hebrew University Of JerusalemInventors: Abraham J. Domb, Shimon Benita, Itzhack Polacheck, Galina Linden
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Patent number: 5977347Abstract: Cellulose acetate propionate is a cellulose ester wherein hydroxyl groups of cellulose are substituted with acetyl and propionyl. Cellulose acetate propionate of the present invention has an amorphous index (Am) of 0.01 to 0.10. The present invention also provides cellulose acetate propionate having a degree of acetyl substitution (DSac) and a degree of propionyl substitution (DSpr) satisfying the formulas (I) to (IV).2.0<DSac.ltoreq.2.95 (I)0.05<DSpr.ltoreq.0.8 (II)2.6<DSac+DSpr.ltoreq.3.0 (III)1.Type: GrantFiled: November 6, 1998Date of Patent: November 2, 1999Assignee: Daicel Chemical Industries, Ltd.Inventors: Yuichiro Shuto, Hiroki Taniguchi
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Patent number: 5977346Abstract: A fatty acid ester of cellulose having excellent transparency, filterability and spinnability in spite of its high content of mannose and xylose, wherein the total molar content of mannose and xylose accounts for at least 7% of that of glucose, mannose and xylose, and the amount of filtration satisfies a specified requirement. Such a fatty acid ester of cellulose is prepared by using a pulp having a low .alpha.-cellulose content as a raw material and a fatty acid corresponding to the ester as a diluent and adding an organic solvent in an amount of at least 10% by weight based on the diluent in any step during the preparation. In the preparation of cellulose diacetate, which excellent filterability and transparency, by the acetic acid process, the cellulose diacetate obtained by aging is dissolved in a solvent which can dissolve it and the resulting cellulose diacetate is recovered.Type: GrantFiled: November 26, 1996Date of Patent: November 2, 1999Assignee: Daicel Chemical Industries, Ltd.Inventors: Shiro Saka, Hiroyuki Matsumura, Naoto Habu, Yoshiaki Kaino, Ryouta Iwata, Tanemi Asai, Syu Shimamoto
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Patent number: 5977327Abstract: An improved method for synthesis of Annamycin is described. The synthesis relies upon a method of selectively deacetylating the Annamycin precursor and purification of the deacetylated product by a filtration step. In addition, the method includes an improved method for desilylating the Annamycin precursor that utilizes acidic conditions. Lastly, improved purification methods of the final Annamycin product are disclosed.Type: GrantFiled: July 22, 1997Date of Patent: November 2, 1999Assignee: Board of Regents, The University of Texas SystemInventors: Krzysztof Dziewiszek, Waldemar Priebe
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Patent number: 5976598Abstract: Particulate cellulosic material such as microcrystalline cellulose, .alpha.-cellulose, and/or cellulose acylated with C.sub.2 to C.sub.24 aliphatic acids to a degree of substitution of about 0.05 or less, and mixtures thereof, are physically coated with an edible hydrophobic polymer to provide low calorie flour/starch replacements for edible compositions. Typical coating polymers include cellulose esters of one or more C.sub.2 to C.sub.24 aliphatic acids; cellulose ethers such as methyl cellulose, ethyl cellulose, hydroxypropyl methyl cellulose, carboxymethyl cellulose, natural waxes such as carnauba wax, candelilla wax, rice bran wax, bees wax, and mixtures of these; petroleum waxes such as polyethylene and paraffin waxes; proteins, preferably hydrophobic, such as zein, glutenin and the like, and mixtures thereof. In preferred embodiments, the low calorie flour replacements are made in a hot melt process with intense mixing in the absence of emulsifiers and gums.Type: GrantFiled: November 4, 1997Date of Patent: November 2, 1999Assignee: Nabisco, Inc.Inventors: Daniel Akkaway, Denise Deming, Lawrence Klemann, Juan A. Menijvar, Louise Slade, Ronald D'Amelia, Jeffery T. Galbraith, Haresh P. Madera, Robert M. Sauer, Jr., Ronald G. Yarger, Xiaoming You
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Patent number: 5973139Abstract: A process for preparing a carboxylated cellulose ester from oxidized cellulose is described. The carboxylated cellulose esters have improved solvent solubility and coating resin compatibility when compared to cellulose esters made from regular grade cellulose. The process comprises activating the oxidized cellulose with water. The activated oxidized cellulose is then dehydrated by displacing the water with acetic acid and optionally displacing at least some of the acetic acid with butyric acid or propionic acid. After dehydration the activated cellulose is reacted with an esterifying reagent in the presence of a catalyst at about 0.degree. C. The temperature is gradually increased to a level sufficient to complete reaction and to obtain an intrinsic viscosity ranging from about 0.2 to about 1.6 dl/g. The reacted solution is then hydrolyzed to obtain a hydroxyl content ranging from about 0.05 to about 1.0.Type: GrantFiled: February 6, 1998Date of Patent: October 26, 1999Assignee: Eastman Chemical CompanyInventors: Benedict Moonsang Lee, Chung-Ming Kuo, Jessica Posey-Dowty, Larry Gerald Curtis
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Patent number: 5965407Abstract: The present invention relates to compound 0624 having excellent antitumor activity and antimicrobial activity, which is represented by the general formula (1), and a pharmaceutically acceptable salt thereof. ##STR1## (wherein R represents H or COCH.sub.3.Type: GrantFiled: March 3, 1998Date of Patent: October 12, 1999Assignee: Higeta Shoyu Co. Ltd.Inventors: Yasushi Tanaka, Yuzuru Mikami, Katsukiyo Yazawa
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Patent number: 5958889Abstract: 7-O-(4-Amino-2,4,6-trideoxy-2-fluoro-.alpha.-L-mannopyranosyl)daunomycinone or -adriamycinone is now synthesized as a daunomycinone or adriamycinone derivative having the general formula ##STR1## wherein R is a hydrogen atom or hydroxyl group. These novel compounds according to this invention exhibit excellent antitumor activities and have a high solubility in water, and hence they are useful as an antitumor agent.Type: GrantFiled: December 22, 1997Date of Patent: September 28, 1999Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Tomio Takeuchi, Sumio Umezawa, Tsutomu Tsuchiya, Yasushi Takagi
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Patent number: 5955100Abstract: Glycosyl-spacer-drugs compounds (prodrugs), their preparation and their use as pharmaceuticals are described.Type: GrantFiled: May 24, 1995Date of Patent: September 21, 1999Assignees: Behringwerke Aktiengesellschaft, Laboratories Hoechst S/AInventors: Klaus Bosslet, Jorg Czech, Dieter Hoffmann, Cenek Kolar, Fran.cedilla.ois Tillequin, Jean-Claude Florent, Michel Azoulay, Claude Monneret, Jean-Claude Jacquesy, Jean-Pierre Gesson, Michel Koch
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Patent number: 5948896Abstract: A process for the preparation of 13-deoxy deoxyanthracycline derivatives.Type: GrantFiled: August 13, 1997Date of Patent: September 7, 1999Assignee: GEM PharmaceuticalsInventor: Xini Zhang
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Patent number: 5948750Abstract: Chemical conjugates which comprise oligopeptides, having amino acid sequences that are selectively proteolytically cleaved by free prostate specific antigen (PSA) and known cytotoxic agents are disclosed. Such conjugates are useful in the treatment of prostatic cancer and benign prostatic hypertrophy (BPH).Type: GrantFiled: October 14, 1997Date of Patent: September 7, 1999Assignee: Merck & Co., Inc.Inventors: Victor M. Garsky, Deborah Defeo-Jones, Dong-Mei Feng
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Patent number: 5942605Abstract: 5-imino-13-deoxy anthracycline derivatives, medical uses of 5-imino-13-deoxy anthracycline derivatives and methods for preparing 5-imino-13-deoxy anthracycline derivatives.Type: GrantFiled: March 3, 1998Date of Patent: August 24, 1999Assignee: GEM Pharmaceuticals, Inc.Inventors: Xini Zhang, Richard D. Olson
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Patent number: 5906852Abstract: Cellulose is surface-modified by coating and/or acylation with C.sub.2 to C.sub.24, in some cases primarily C.sub.6 to C.sub.22, or more narrowly C.sub.16 to C.sub.20, aliphatic acids, to obtain cellulose esters exhibiting a degree of substitution of about 0.05 or less, preferably about 0.01 or less. The surface-modified cellulose is used as a low-calorie carbohydrate replacement in edible compositions having a carbohydrate component. Baked food products such as cookies employ the low-calorie ingredient in place of a starch ingredient in some preferred embodiments. In some of these embodiments, cookies formulated with surface-modified cellulose further contain a spreading ingredient such as polydextrose; in these, the cellulose esters help to control the spread as well as provide calorie reduction. In these and other embodiments, the food products can also contain reduced fat or a low calorie fat substitute and/or an artificial sweetener to provide further calorie reduction.Type: GrantFiled: November 4, 1997Date of Patent: May 25, 1999Assignee: Nabisco, Inc.Inventors: Lawrence P. Klemann, Ronald G. Yarger, Xiaoming You
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Patent number: 5877158Abstract: Substrate-spacer-prodrug compounds (pro-prodrugs) suited for site specific delivery of drugs, a process of preparing them and their use are described.Type: GrantFiled: September 20, 1994Date of Patent: March 2, 1999Assignees: Behringwerke Aktiengesellschaft, Laboratoires Hoechst S/AInventors: Klaus Bosslet, Jorg Czech, Dieter Hoffmann, Fran.cedilla.ois Tillequin, Jean-Claude Florent, Michel Azoulay, Claude Monneret, Jean-Claude Jacquesy, Jean-Pierre Gesson, Michel Koch
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Patent number: 5874550Abstract: This invention relates to a novel method for the chemical preparation of epirubicin or acid addition salts thereof, in particular the HCl salt, from daunorubicin. This process avoids the disadvantages of the prior art. First daunorubicin is methanolized to obtain daunomycinone and daunosamine methyl ether in very high yields. Daunomycinone is converted to 14-acetoxy daunomycinone by bromination and acetoxylation, while daunosamine methyl ether is converted into an N-protected 4'-epi daunosamine. The choice of the protecting group of the amino group of the daunosamine methyl ether is important because it has to be removed after coupling the sugar with the aglycone without causing side reactions of the aglycone. Two protecting groups were selected: the trifluoroacetyl group and the allyloxycarbonyl group.Type: GrantFiled: December 4, 1997Date of Patent: February 23, 1999Assignee: Pharmachemie B.V.Inventors: Marcel van der Rijst, Johan Wilhelm Scheeren, Dick de Vos
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Patent number: 5874412Abstract: The present invention discloses new and novel bisanthracyclines linked through the saccharide portions. These compounds show high activity against two clinically relevant mechanisms of resistance. A novel approach of the invention produces compounds that are as active or more so than the parent compounds. Furthermore, the inventor's discovery is also for the design of effective DNA-binding bisanthracyclines as well as anthracyclines mixed with other intercalators and groove binders.Type: GrantFiled: March 21, 1997Date of Patent: February 23, 1999Inventors: Waldemar Priebe, Jonathan B. Chaires, Teresa Przewloka, Izabela Fokt, Roman Perez-Soler
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Patent number: 5874549Abstract: A bicyclic, non-aromatic hydrocarbon compound, optionally having one or more N, O or S atoms in the bicyclic skeleton, and having as substituents an acid group and an amido group, which are vicinal and in a syn-position, wherein the amido group is not anilido and the acid group is carboxyl or carboxyl in a form metabolizable to a free carboxyl group, and wherein said bicyclic skeleton is optionally unsaturated, except in the bond between said groups, acid-cleavably links an amide-containing active agent to a targeting agent, which is linked by a linker arm to the bicyclic skeleton.Type: GrantFiled: September 9, 1993Date of Patent: February 23, 1999Assignee: NeoRx CorporationInventor: Stephen Hadley
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Patent number: 5861492Abstract: The invention relates to methods that permit the rapid construction of oligosaccharides and other glycoconjugates. Methods for forming multiple glycosidic linkages in solution in a single step are disclosed. The invention takes advantage of the discovery that the relative reactivity of glycoside residues containing anomeric sulfoxides and nucleophilic functional groups can be controlled. In another aspect of the invention, the reactivity of activated anomeric sugar sulfoxides is utilized in a solid phase method for the formation of glycosidic linkages. The methods disclosed may be applied to the preparation of specific oligosaccharides and other glycoconjugates, as well as to the preparation of glycosidic libraries comprising mixtures of various oligosaccharides, including glycoconjugates, which can be screened for biological activity.Type: GrantFiled: January 9, 1997Date of Patent: January 19, 1999Assignee: The Trustees of Princeton UniversityInventor: Daniel Evan Kahne
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Patent number: 5856468Abstract: Cellulose acetate propionate is a cellulose ester wherein hydroxyl groups of cellulose are substituted with acetyl and propionyl. Cellulose acetate propionate of the present invention has an amorphous index (Am) of not more than 0.4. Cellulose acetate propionate has a degree of acetyl substitution (DSac) and a degree of propionyl substitution (DSpr), which preferably satisfy the formulas (I) to (III), and more preferably satisfy the formulas (I) to (IV). The present invention also provides a solution of cellulose acetate propionate and a cellulose acetate propionate film. (I) 2.0<DSac.ltoreq.2.95(II) 0.05<DSpr.ltoreq.0.8(III) 2.6<DSac+DSpr.ltoreq.3.0(IV) 1.Type: GrantFiled: July 30, 1997Date of Patent: January 5, 1999Assignee: Daicel Chemical Industries, Ltd.Inventors: Yuichiro Shuto, Hiroki Taniguchi
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Patent number: 5843735Abstract: Aklavinone C-11 hydroxylase separated from Streptomyces sp.; a gene encoding same; an expression vector comprising said gene; a microorganism transformed with said vector; and a process for preparing novel hybrid anthracyclines by using said vector.Type: GrantFiled: October 31, 1995Date of Patent: December 1, 1998Assignees: Korea Institute of Science and Technology, IL Dong Pharmaceutical Co., Ltd.Inventors: Jung-Joon Lee, Young-Ho Kim, Soon-Kwang Hong, Young-Soo Hong, Cheol-Kyu Hwang, Hang-Sub Kim
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Patent number: 5843908Abstract: The present invention relates to novel antifungal antibiotics herein designated as pradimicin L and pradimicin FL, and derivatives thereof. Pradimicins L and FL are produced by Actinomadura verrucosospora subsp. neohibisca strain R103-3, ATCC No. 53930.Type: GrantFiled: September 28, 1990Date of Patent: December 1, 1998Assignee: Bristol-Myers Squibb CompanyInventors: Yosuke Sawada, Kyoichiro Saitoh, Masami Hatori, Takeo Miyaki, Toshikazu Oki, Koji Tomita
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Patent number: 5837828Abstract: The present invention concerns neutral sugar derivatives of pradimicins, their use as antifungal agents, methods for their preparation, and intermediates for their synthesis.Type: GrantFiled: May 2, 1995Date of Patent: November 17, 1998Assignee: Bristol-Myers Squibb Co.Inventors: Shimpei Aburaki, Tetsuro Yamasaki, Toshikazu Oki, Seiji Iimura, Hajime Kamachi, Hideo Kamei, Takayuki Naito
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Patent number: 5814608Abstract: 8-fluoro-anthracyclines of formula (I) have anti-tumor activity. ##STR1## wherein: R is chosen in the group consisting of H, OH, OR.sub.4 wherein R.sub.4 is chosen in the group consisting of CHO, COCH.sub.3, acyl derivative of a carboxylic acid containing up to 6 carbon atoms;R.sub.1 is chosen in the group consisting of: H, OH, OCH.sub.3 ;R.sub.2 is chosen in the group consisting of: H, OH, NH.sub.2R.sub.3 is chosen in the group consisting of: H, OH, NH.sub.2, residue of formula (A) ##STR2## The compounds are characterized by having cis-stereochemistry between the groups 8--F and 9--OH. Their preparation and pharmaceutical compositions containing them are also described.Type: GrantFiled: April 21, 1997Date of Patent: September 29, 1998Assignees: Bristol-Myers Squibb, S.p.A., A. Menarini Industrie Farmaceutiche Riunite S.R.L.Inventors: Fabio Animati, Federico Arcamone, Giuseppe Giannini, Paolo Lombardi, Edith Monteagudo
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Patent number: 5807835Abstract: New 8-fluoroanthracycline derivatives of formula I possessing antitumoral properties are described, together with their preparation and pharmaceutical compositions containing them.Type: GrantFiled: May 14, 1991Date of Patent: September 15, 1998Assignee: A. Menarini Industrie Farmaceutiche Riunite S.r.l.Inventors: Fabio Animati, Paolo Lombardi, Federico Arcamone
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Patent number: 5801152Abstract: The present invention is referred to compounds of general formula (I) and (II), respectively ##STR1## their pharmaceutically acceptable salts, the process for their preparation, and the pharmaceutical compositions containing them.Type: GrantFiled: March 28, 1996Date of Patent: September 1, 1998Assignees: A. Menarini Industrie Farmaceutiche Riunite S.r.l., Bristol-Myers Squibb S.p.A.Inventors: Fabio Animati, Paolo Lombardi, Frederico Arcamone, Amalia Cipollone
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Patent number: 5792839Abstract: The invention relates to methods that permit the rapid construction of oligosaccharides and other glycoconjugates. Methods for forming multiple glycosidic linkages in solution in a single step are disclosed. The invention takes advantage of the discovery that the relative reactivity of glycoside residues containing anomeric sulfoxides and nucleophilic functional groups can be controlled. In another aspect of the invention, the reactivity of activated anomeric sugar sulfoxides is utilized in a solid phase method for the formation of glycosidic linkages. The methods disclosed may be applied to the preparation of specific oligosaccharides and other glycoconjugates, as well as to the preparation of glycosidic libraries comprising mixtures of various oligosaccharides, including glycoconjugates, which can be screened for biological activity.Type: GrantFiled: January 10, 1997Date of Patent: August 11, 1998Assignee: Trustees of Princeton UniversityInventor: Daniel Evan Kahne
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Patent number: 5789386Abstract: To provide novel fluorine-containing anthracycline derivatives having high antitumor activities and a solubility in water, there have now been synthesized a 7-O-(2,6-dideoxy-2-fluoro-3-O- or -4-O- or -3,4-di-O-aminoalkanoyl-.alpha.-L-talopyranosyl)daunomycinone or -adriamycinone of general formula (I) shown below, as well as a 7-O-(3-O- or -4-O- or -3,4-di-O-aminoalkanoyl-2,6-dideoxy-2,6,6,6-tetrafluoro-.alpha.-L-talopyra nosyl- or -2,6-dideoxy-6,6,6-trifluoro-.alpha.-L-lyxo-hexopyranosyl)adriamycinone of general formula (II) shown below:General formula (I) ##STR1## General formula (II) ##STR2## wherein either one or both of A.sup.1 and A.sup.2 is or are an .alpha.-amino acid residue or an .omega.-amino acid residue and T denotes a fluorine or hydrogen atom. The novel fluorine-containing anthracycline derivatives of general formulae (I) and (II) are highly active against tumors and soluble in water, and they are useful as antitumor agents administrable in the form of injectable solution.Type: GrantFiled: September 9, 1996Date of Patent: August 4, 1998Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Tomio Takeuchi, Sumio Umezawa, Tsutomu Tsuchiya, Yasushi Takagi, Hiromi Sohtome
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Patent number: 5780585Abstract: A prodrug of the formula (I): ##STR1## where R.sup.1 is a group such that the compound R--NH.sub.2 represents actinomycin D, doxorubicin, mitomycin C, or a nitrogen mustard of the formula (IV): ##STR2## a prodrug of the formula (II): ##STR3## where R.sup.1 is a group such that the compound R.sup.2 OH is a phenolic nitrogen mustard; and processes whereby the prodrugs shown above are made in which a prodrug precursor compound is reacted with 4-nitrobenzyl chloroformate under anhydrous conditions.Type: GrantFiled: June 7, 1995Date of Patent: July 14, 1998Assignee: Cancer Research Campaign Technology LimitedInventors: Gillian Anlezark, Roger Melton, Roger Sherwood, Thomas Connors, Frank Friedlos, Michael Jarman, Richard Knox, Anthony Mauger, Caroline Joy Springer
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Patent number: 5750677Abstract: The present invention relates to a process for preparing cellulose esters having a total DS/AGU of 0.1 to 3.0, said process comprising contacting the following:(i) a cellulose material,(ii) a solubilizing amount of a solvent system comprising a carboxamide diluent or a urea-based diluent,(iii) an acylating reagent, and(iv) a titanium-containing compound.Type: GrantFiled: December 30, 1994Date of Patent: May 12, 1998Assignee: Eastman Chemical CompanyInventors: Kevin J. Edgar, Richard T. Bogan
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Patent number: RE38435Abstract: A mixture of chemical substances such as optical isomers, geometrical isomers and polymers having different molecular weight ranges is separated to each ingredient by use of a cellulose derivative having an aromatic ring in the chromatographic method.Type: GrantFiled: September 22, 1997Date of Patent: February 24, 2004Assignee: Daicel Chemical Industries, Ltd.Inventors: Yoshio Okamoto, Koichi Hatada, Tohru Shibata, Ichiro Okamoto, Hiroyuki Nakamura