Processes Patents (Class 536/18.5)
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Patent number: 7282150Abstract: A method for extracting a hydrophobic group-containing water-soluble organic compound, comprising the step of bringing an aqueous solution containing the hydrophobic group-containing water-soluble organic compound and a saccharide into contact with a polar organic solvent to obtain an aqueous phase and an organic phase, whereby the hydrophobic group-containing water-soluble organic compound is transferred to the organic phase. The saccharide concentration of the aqueous solution may be at least 12 g per 100 ml of the aqueous solution. The aqueous solution may further contain a phase separation assisting agent. The phase separation assisting agent may be selected from the group consisting of sodium chloride, sodium citrate, magnesium sulfate, and ammonium sulfate.Type: GrantFiled: September 19, 2002Date of Patent: October 16, 2007Assignee: Ezaki Glico Co., Ltd.Inventors: Takashi Kuriki, Takahisa Nishimura, Kazuhisa Sugimoto
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Patent number: 7241875Abstract: An aqueous surfactant mixture comprised of an alkyl and/or alkenyl oligoglycoside ether carboxylic acid is made by a process comprising reacting in an aqueous solution an alkyl and/or alkenyl oligoglycoside and an ?-halocarboxylic acid or a salt or ester thereof in the presence of alkali.Type: GrantFiled: April 27, 2002Date of Patent: July 10, 2007Assignee: Cognis Deutschland GmbH & Co. KGInventors: Karl Heinz Schmid, Almud Folge, Ansgar Behler
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Patent number: 7235646Abstract: The present invention relates to an improved, cost effective and easy process for the preparation of azithromycin monohydrate isopropanol clathrate. The process provides a one-step method of preparing azithromycin monohydrate isopropanol clathrate directly from 9-deoxo-9a-aza-9a-homoerythromycin A. The process comprises at least partial dissolution and/or suspension of 9-deoxo-9a-aza-9a homoerythromycin A in isopropanol to form a mixture, adding methylating solution to the said mixture, refluxing or heating said mixture to form a reaction mixture, adding alkaline solution to the reaction mixture to adjust pH from about 10 to about 11 and isolating pure azithromycin monohydrate isopropanol clathrate. The process helps in reducing the total time of preparation, total utility cost for the production and also helps to avoid handling loss.Type: GrantFiled: June 27, 2005Date of Patent: June 26, 2007Assignee: Alembic LimitedInventors: Dhiren Natavarlal Mistry, Mahadeo Maroti Thorat, Kamlesh Sanmukhubhia Soni, Vinod Kumar Kansal
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Patent number: 7211663Abstract: One aspect of the present invention relates to differentially protected glycosyl phosphates. Another aspect of the present invention relates to the preparation of glycosyl phosphates from glycal precursors. In another aspect of the present invention, glycosyl phosphates are used as glycosyl donors in glycosylation reactions.Type: GrantFiled: November 1, 2001Date of Patent: May 1, 2007Assignee: Massachusetts Institute of TechnologyInventors: Peter H. Seeberger, Obadiah J. Plante
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Patent number: 7205394Abstract: A clathrate of azithromycin hydrate with 1,2-propyleneglycol is much less hygroscopic than azithromycin hydrate or crystals known in the art, therefore, it can be useful for the preparation of a medicine for treating various microbial infections.Type: GrantFiled: April 25, 2002Date of Patent: April 17, 2007Assignee: Hanmi Pharm. Co., Ltd.Inventors: Kwee-Hyun Suh, Gi-Jeong Kim, Sang-Min Yoon, Mi-Ra Seong, Gwan-Sun Lee
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Patent number: 7205395Abstract: Azithromycin is prepared in a high yield by a simple process using a crystalline 9-deoxo-9a-aza-9a-homoerythromycin A hydrate.Type: GrantFiled: April 3, 2002Date of Patent: April 17, 2007Assignee: Hanmi Pharm Co., Ltd.Inventors: Gi Jeong Kim, Mi Ra Seong, Sang Min Yun, Kwee Hyun Suh
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Patent number: 7196179Abstract: A method to manufacture calcium gluconolactate as a single molecule, compositions formed thereby, and uses therefor are disclosed and described. In one embodiment, a method of manufacturing calcium gluconolactate by reacting a gluconic acid reaction or an equivalent thereof, such as glucono delta lactone with lactic acid in the presence of calcium hydroxide and water to obtain a calcium gluconolactate molecule having the formula CH2OH—(CHOH)4—COOCaCOO—CH(OH)—CH3 with molecular weight of 324.2994 is presented.Type: GrantFiled: June 23, 2004Date of Patent: March 27, 2007Inventor: Manuel Torres Buendia
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Patent number: 7157432Abstract: Provided is a tetraphenylbacteriochlorin derivative represented by the formula (I): [wherein R1, R2, R3 and R4, independently from each other, are a residue of a monosaccharide represented by the formulae: (wherein, R is a hydrogen or a protecting group)], or its salt. The tetraphenylbacteriochlorin derivative or its salt has a large molar extinction coefficient at long wavelengths which are expected to have a high tissue-penetrating property, and exhibits high selectivity to tumor cells and hydrophilicity.Type: GrantFiled: September 7, 2005Date of Patent: January 2, 2007Assignees: San-Ei Gen F.F.I., Inc.Inventors: Shigenobu Yano, Toyoji Kakuchi, Yuji Mikata
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Patent number: 7148223Abstract: Compounds represented by the formula 1: A is selected from the group consisting of wherein each R individually is H or acyl, Y is X, N3, NH2, monoalkylamino, or dialkylamino; Z is O or S; and X is selected from the group consisting of hydrogen, halo, hydroxy, alkoxy, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, amino, monoalkylamino, dialkylamino, thioaryl, thioalkyl, allylamino, cyano and nitro; tautomers thereof; and pharmaceutically acceptable salts thereof are provided along with methods for their fabrication. Various of these compounds can be used as anticancer agents, or antiviral agents or to inhibit DNA replication.Type: GrantFiled: January 31, 2005Date of Patent: December 12, 2006Assignee: Southern Research InstituteInventors: John A. Secrist, III, Kamal N. Tiwari, John A. Montgomery
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Patent number: 7109182Abstract: A pharmaceutical composition including a therapeutically effective amount of at least one oligomannoside produced by chemical synthesis which is homologous to a wall oligomannoside of an infectious organism or pathogen, or a derivative thereof, and a pharmaceutically acceptable vehicle.Type: GrantFiled: May 23, 2002Date of Patent: September 19, 2006Assignee: Centre Hospitalier Regional Universitaire (CHRU)Inventors: Jacques Esnault, Pierre Sinay, Reynald Chevalier, Jean-Frédéric Colombel, Jean-Maurice Mallet, Boualem Sendid, Thierry Jouault, Daniel Poulain, Pierre-André Trinel
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Patent number: 7071314Abstract: An efficient arylation technique for use in the synthesis of erythromycin derivatives, involving a modified Heck reaction which employs less than six mole percent of palladium catalyst and no phosphine is disclosed. With this modified Heck reaction, an O-alkenylaryl macrolide can be obtained in a much shorter reaction time than under conventional Heck reaction conditions. The modified Heck reaction can be utilized in a method for phosphine-free arylation of an O-allylic erythromycin derivative, in a method for preparing an O-alkenylaryl erythromycin A derivative, or in a method for preparing a 2?, 4?-hydroxyl protected 6-O-alkenylaryl erythromycin A derivative.Type: GrantFiled: May 28, 2002Date of Patent: July 4, 2006Assignee: Abbott LaboratoriesInventors: Weijang Zhang, Margaret Chi-Ping Hsu, Anthony R. Haight, Matthew John Peterson, Bikshandarkoil A. Narayanan
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Patent number: 7049417Abstract: Novel 6,11-4-carbon bridged ketolides, pharmaceutically-acceptable compositions comprising a therapeutically effective amount of a compound of the invention in combination with a pharmaceutically-acceptable carrier are described. Also described are a method for treating bacterial infections by administering to an animal a pharmaceutical composition containing a therapeutically effective amount of a compound of the invention and processes for the preparation of such compounds.Type: GrantFiled: May 7, 2004Date of Patent: May 23, 2006Assignee: Enanta Pharmaceuticals, Inc.Inventors: Yat Sun Or, Guoqiang Wang, Deqiang Niu, Ly Tam Phan
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Patent number: 7045506Abstract: The invention relates to a series of polyglycoside derivatives that contain water-soluble groups introduced into the molecule by reaction with the hydroxyl groups present in the starting polyglycoside molecule, with the chloro material. The preferred products have more than one water-soluble group per molecule and are made with mild reagents to avoid discoloration and mal odor. The most preferred products have between 2 and 3 functional groups per molecule.Type: GrantFiled: July 7, 2003Date of Patent: May 16, 2006Assignee: Colonial Chemical INCInventors: Anthony J. O'Lenick, Jr., Kevin A. O'Lenick
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Patent number: 7038039Abstract: A desired isomer is selectively prepared by phosphorolyzing and isomerizing an anomer mixture of a 1-phosphorylated saccharide derivative while crystallizing one of the isomers to displace the equilibrium. Furthermore, using the action of a nucleoside phosphorylase, a nucleoside is prepared from the 1-phosphorylated saccharide derivative obtained and a base with improved stereoselectivity and a higher yield. This process is an anomer-selective process for preparing a 1-phosphorylated saccharide derivative and a nucleoside.Type: GrantFiled: February 13, 2001Date of Patent: May 2, 2006Assignee: Mitsui Chemicals, Inc.Inventors: Hironori Komatsu, Hirokazu Awano, Nobuyuki Fukazawa, Kiyoshi Ito, Ichirou Ikeda, Tadashi Araki, Takeshi Nakamura, Tamotsu Asano, Junya Fujiwara, Tomoyuki Ando, Katsutoshi Tsuchiya, Kyoko Maruyama, Hideki Umetani, Takahiro Yamauchi, Hitoki Miyake
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Patent number: 7022679Abstract: The present invention relates to processes and intermediates for the preparation of 6–11 bicyclic erythromycin derivatives.Type: GrantFiled: January 14, 2004Date of Patent: April 4, 2006Assignee: Enanta Pharmaceuticals, Inc.Inventors: Heejin Kim, Guoqiang Wang, Yat Sun Or, Zhe Wang
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Patent number: 7019131Abstract: The reactivity of a number of p-methylphenyl thioglycoside (STol) donors which are either fully protected or have one hydroxyl group exposed has been quantitatively determined by HPLC in conjunction with the development of a broadly applicable approach for a facile one-pot synthesis of oligosaccharides. The influence on reactivity of the structural effects of different monosaccharide cores and different protecting groups on each glycoside donor is characterized and quantified. In addition, a correlation between glycosyl donor reactivity and the chemical shift of the anomeric proton by 1 H NMR has been established. A database of thioglycosides as glycosyl donors has been created using this reactivity data. The utility is demonstrated by the easy and rapid one-pot assembly of various linear and branched oligosaccharide structures.Type: GrantFiled: March 25, 2003Date of Patent: March 28, 2006Assignee: The Scripps Research InstituteInventors: Chi-Huey Wong, Zhiyuan Zhang, Ian Ollmann, Timor Baasov, Xin-Shan Ye
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Patent number: 7001994Abstract: Methods to introduce highly phosphorylated mannopyranosyl oligosaccharide derivatives containing mannose 6-phosphate (M6P), or other oligosaccharides bearing other terminal hexoses, to carbonyl groups on oxidized glycans of glycoproteins while retaining their biological activity are described. The methods are useful for modifying glycoproteins, including those produced by recombinant protein expression systems, to increase uptake by cell surface receptor-mediated mechanisms, thus improving their therapeutic efficacy in a variety of applications.Type: GrantFiled: January 17, 2002Date of Patent: February 21, 2006Assignee: Genzyme CorporationInventor: Yunxiang Zhu
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Patent number: 6987175Abstract: The present invention relates to processes for converting clarithromycin Form I to clarithromycin Form II, which include slurrying clarithromycin the Form I in water. The present invention also relates to processes for the preparation of clarithromycin Form II by converting erythromycin A to clarithromycin and thereafter converting clarithromycin Form I to clarithromycin Form II by slurrying.Type: GrantFiled: June 10, 2003Date of Patent: January 17, 2006Assignee: Teva Pharmaceutical Industries Ltd.Inventors: Igor Lifshitz, Ilya Avrutov, Edi Schwartz, Basem Masarwa
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Patent number: 6960654Abstract: A method of forming a glycosidic bond utilizing an activated thioglycoside is disclosed. The thioglycoside is activated by an N,N-dialkylsulfinamide and trifluoromethanesulfonic anhydride. The method allows the facile synthesis of disaccharides, oligosacchraides, and polysaccharides in solution or on a polymer support.Type: GrantFiled: June 2, 2003Date of Patent: November 1, 2005Assignee: The Board of Trustees of the University of IllinoisInventors: David C. Crich, Mark Smith
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Patent number: 6958314Abstract: A petro-chemical free nonionic surfactant is prepared by the alkylation of an alkyl polyglucoside (APG). Under suitable alkylation reaction conditions, the surfactants are preferably prepared by the reaction of an APG with either alkyl halide or an alkyl tosylate. These surfactants are low foaming and exhibit excellent detergency.Type: GrantFiled: March 5, 2003Date of Patent: October 25, 2005Assignee: Master Chemical CorporationInventor: David B. McCall
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Patent number: 6958389Abstract: Provided is a tetraphenylbacteriochlorin derivative represented by the formula (I): [wherein R1, R2, R3 and R4, independently from each other, are a residue of a monosaccharide represented by the formulae: (wherein, R is a hydrogen or a protecting group)], or its salt. The tetraphenylbacteriochlorin derivative or its salt has a large molar extinction coefficient at long wavelengths which are expected to have a high tissue-penetrating property, and exhibits high selectivity to tumor cells and hydrophilicity.Type: GrantFiled: September 6, 2001Date of Patent: October 25, 2005Assignees: San-Ei Gen F.F.I. Inc.Inventors: Shigenobu Yano, Toyoji Kakuchi, Yuji Mikata
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Patent number: 6953850Abstract: The invention provides collections of orthogonally-protected monosaccharides as universal building blocks for the synthesis of glycoconjugates of non-carbohydrate molecules, neo-glycoconjugates and oligosaccharides. This orthogonal protection strategy allows for the specific deprotection of any substituent ono the saccharide ring, and greatly facilitates targeted or library-focused carbohydrate-related syntheses. In particular, the invention provides a universal monosaccharide building block of General Formula (I) or General Formula (II) in which A is a leaving group; X is hydrogen, O, N or N3; X1 is hydrogen, —CH2O—, —CH2NH—, —CH3, —CH2N3 or —COO—; and B, C, D and E are protecting groups that can be cleaved orthogonally, and in which B, C, D and E are absent when X is hydrogen or N3, and E is absent when X1 is hydrogen, CH3 or N3.Type: GrantFiled: January 18, 2000Date of Patent: October 11, 2005Assignee: Alchemia Pty. Ltd.Inventors: Gyula Dekany, John Papagerogiou, Laurent Francois Bornaghi
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Patent number: 6949524Abstract: Compounds that are modified polysaccharides having pendant aldehyde functionalities are disclosed. Each of the aldehyde functionalities is attached through a linker to a position corresponding to a hydrogen atom of a different hydroxyl group of unmodified polysaccharide. Also disclosed is a method for introducing an amine-reactive functionality into a dextran. The method comprises (a) reacting the dextran with an alkylating agent having a functionality that reacts with an hydroxyl group of the dextran thereby forming an alkylated dextran wherein the alkylating agent has an olefin group and (b) treating the alkylated dextran to convert the olefin group to an amine-reactive functionality. A polysaccharide can be conjugated to a biomolecule by carrying out the above method and reacting the amine-reactive functionality with an amine functionality on the biomolecule to produce polysaccharide conjugated to the biomolecule.Type: GrantFiled: July 2, 2002Date of Patent: September 27, 2005Assignee: Dade Behring Marburg GmbHInventors: Rajendra Singh, Harshvardhan Mehta
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Patent number: 6949519Abstract: Azithromycin in the form of a monohydrate comprising from 4.0% to 6.5% of water, a process for its preparation and its use in pharmaceutical compositions.Type: GrantFiled: November 26, 2001Date of Patent: September 27, 2005Assignee: Sandoz AGInventors: Victor Centellas, José Diago, Rafael Garcia, Johannes Ludescher
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Patent number: 6936588Abstract: The present invention relates to a method for the production and use of enteral nutrients, particularly an enteral solution, wherein this method is distinguished by a particularly gentle processing, particularly of the carbohydrate components contained in the solution.Type: GrantFiled: October 10, 2003Date of Patent: August 30, 2005Assignee: Südzucker Aktiengesellschaft Mannheim/OchsenfurtInventors: Jörg Kowalczyk, Gunhild Kozianowski, Markwart Kunz, Matthias Moser
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Patent number: 6936591Abstract: Substantially pure amorphous 9-deoxo-9a-aza-9a-methyl-9a-homoerythromycin A. In addition, this disclosure is directed to a process for the preparation thereof from crude 9-deoxo-9a-aza-9a-methyl-9a-homoerythromycin A via orthorhombic isostructural pseudopolymorphs of 9-deoxo-9a-aza-9a-methyl-9a-homoerythromycin A, of the general formula I: wherein S represents a water-miscible or water-immiscible organic solvent, characterized by the orthorhombic space group P212121, with average unit cell parameters a=8.2 to 9.7 ?, b=11.5 to 13.5 ?, c=44.5 to 47.0 ?, ?=?=?=90°, wherein a, b and c represent the crystal axes lengths and ?, ? and ? represent the angles between the crystal axes.Type: GrantFiled: July 21, 2003Date of Patent: August 30, 2005Assignee: Pliva Pharmaceutical Industry, IncorporatedInventors: Miljenko Dumić, Mladen Vinković, Marina Oresic, Ernest Mestrovic, Aleksandar Danilovski, Alojz Dumbovic, Knezevic Zdravka, Gorjana Lazarevski, Darko Filic, Dominik Cincic, Katica Lazaric, Dejan-Kresimir Bucar
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Patent number: 6936710Abstract: Primary hydroxyl groups in a substrate having both primary and secondary hydroxyl groups can be selectively oxidized to carbaldehyde and/or carboxyl groups by contacting the substrate with a cyclic nitroxyl compound in the presence of a peroxosulfate as a co-oxidant and by carrying out the reaction at a temperature below 30° C. and at a pH below 9. The process is halogen-free and metal-free and is especially suitable for oxidizing polysaccharides.Type: GrantFiled: December 13, 2001Date of Patent: August 30, 2005Assignee: SCA Hygiene Products Zeist B.V.Inventors: Petter Bragd, Arie Cornelis Besemer
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Patent number: 6927211Abstract: Compositions and methods are provided for use in the treatment of cancer.Type: GrantFiled: December 4, 2003Date of Patent: August 9, 2005Assignee: Bristol-Myers Squibb CompanyInventors: Giorgio Minotti, Luca Gianni
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Patent number: 6921841Abstract: It is described a process for the synthesis of optically active anthracyclines by the fact that the key intermediate (R)2-acetyl-2-hydroxy-1,2,3,4-tetrahydronaphtalene 5,8-dialkoxy-3,4-dihydronaphtalene by acylation asymmetric dihydroxylation, transformation into chloroacetate, dehydrochloridation and final hydrolysis.Type: GrantFiled: November 15, 2001Date of Patent: July 26, 2005Assignee: Menarini Richerche S.p.A.Inventors: Cristina Di Bugno, Fabio D'Arata, Alessio Ramacciotti, Paolo Crotti
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Patent number: 6916792Abstract: The present invention is to provide a process for producing a 2?-O-acetyl-4?-formyl-8,9-anhydroerythromycin A 6,9-hemiketal compound 4, and it provide a process for producing an erythromycin compound which comprises reacting a formylating agent with a 2?-O-acetylerythromycin A compound 2 to obtain 2-?-O-acetyl-4?-O-formylerythromycin A compound 3, then, acting an acid on Compound 3 to subject to hemiketalation, and then adding an aqueous basic solution in an aqueous solution to precipitate Compound 4 as free crystals.Type: GrantFiled: June 12, 2002Date of Patent: July 12, 2005Assignees: UBE Industries, Ltd., Chugai Seiyaku Kabushiki KaishaInventors: Hiroyuki Miyata, Akira Takama, Tatsuya Kawaguchi, Kazuma Sakata, Kikuo Ataka, Masayoshi Oku, Hiroyuki Suenaga
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Patent number: 6916920Abstract: A process for producing hydrazinomonosaccharide derivatives and use of hydrazines in determining the structures of aldose and ketose monosaccharides located at the reducing ends of saccharides.Type: GrantFiled: July 30, 2001Date of Patent: July 12, 2005Assignee: Takara Bio Inc.Inventors: Tsuyoshi Miyamura, Tomoe Egashira, Mutsumi Sano, Brad K. Bendiak, Ikunoshin Kato
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Patent number: 6914061Abstract: Compounds represented by the formula 1: A is selected from the group consisting of wherein each R individually is H or acyl, Y is X, N3, NH2, monoalkylamino, or dialkylamino; Z is O or S; and X is selected from the group consisting of hydrogen, halo, hydroxy, alkoxy, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, amino, monoalkylamino, dialkylamino, thioaryl, thioalkyl, allylamino, cyano and nitro; tautomers thereof; and pharmaceutically acceptable salts thereof are provided along with methods for their fabrication. Various of these compounds can be used as anticancer agents, or antiviral agents or to inhibit DNA replication.Type: GrantFiled: September 9, 2002Date of Patent: July 5, 2005Assignee: Southern Research InstituteInventors: John A. Secrist, III, Kamal N. Tiwari, John A. Montgomery
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Patent number: 6906039Abstract: The present invention is to provide a process for producing a 2?-O-acetyl-4?-O-formyl-8,9-anhydroerythromycin A 6,9-hemiketal compound 4, and it provide a process for producing an erythromycin compound which comprises reacting a formylating agent with a 2?-O-acetylerythromycin A compound 2 to obtain 2?-O-acetyl-4?-O-formylerythromycin A compound 3, then, acting an acid on Compound 3 to subject to hemiketalation, and then adding an aqueous basic solution in an aqueous solution to precipitate Compound 4 as free crystals.Type: GrantFiled: June 12, 2002Date of Patent: June 14, 2005Assignees: Ube Industries, Ltd., Chugai Seikyaku Kabushiki KaishaInventors: Hiroyuki Miyata, Akira Takama, Yasuhito Yamamoto, Kikuo Ataka
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Patent number: 6906040Abstract: Compositions and methods are provided for use in the treatment of cancer.Type: GrantFiled: September 18, 2001Date of Patent: June 14, 2005Assignee: Bristol-Myers Squibb CompanyInventors: Giorgio Minotti, Luca Gianni
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Patent number: 6906184Abstract: An improved process for the preparation of the antiparasitic compound 25-cyclohexyl-22,23-dihydro-5-hydroxyiminoavermectin B1 monosaccharide from doramectine and intermediates therefor and crystalline solvates thereof.Type: GrantFiled: July 23, 1998Date of Patent: June 14, 2005Assignee: Pifzer, Inc.Inventors: Nigel D. Walshe, Selena J. Cambers
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Patent number: 6900295Abstract: The present invention is an enzyme-decomposable polymer compound having recyclable decomposition products. The polymeric compound is a glycopolymer of a saccharide having only glucopyranose rings and a second component. In addition, the glycopolymer may contain molecular chains having at least one type of repeating unit, which chains are crosslinked by a saccharide having only glucopyranose rings.Type: GrantFiled: November 13, 2001Date of Patent: May 31, 2005Assignee: Canon Kabushiki KaishaInventors: Hiroyoshi Kishi, Toyoko Kobayashi, Kiyoshi Sakai, Norio Kaneko, Kazumi Tanaka, Chieko Mihara, Toshihiko Takeda, Yoshihiko Kikuchi
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Patent number: 6900296Abstract: The invention relates to a cost effective and industrially advantageous process for the selective methylation of a hydroxy group at the 6 position of erythromycin A derivative which comprised methylating the erythromycin A derivative with a methylating agent in a mixture of toluene and a ploar aprotic solvent.Type: GrantFiled: May 7, 2001Date of Patent: May 31, 2005Assignee: Ranbaxy Laboratories LimitedInventors: Mohammad Salman, Parma Chandra Ray, Kiran Kumar Gangakhedkar, Harish Niranjan Lal Dorwal, Naresh Kumar
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Patent number: 6897299Abstract: A method for preparing a fumarate salt of a compound represented by Formula (II): (wherein R1 represents a hydrogen atom or a lower alkyl group, and R2 represents a lower alkyl group), which comprises carbamating a compound represented by Formula (I): (wherein R1 represents a hydrogen atom or a lower alkyl group), removing all carbamate groups from this compound, alkylating the nitrogen atom at the 3?-position of the desosamine ring in the resulting compound to give the compound represented by Formula (II), and converting this compound into a fumarate salt, wherein the compound represented by Formula (I) is carbamated in the presence of a cyclic ether or a carboxylic ester. This method enables efficient preparation of high-quality erythromycin derivatives.Type: GrantFiled: August 31, 2001Date of Patent: May 24, 2005Assignee: Chugai Seiyaku Kabushiki KaishaInventors: Hitoshi Shimizu, Kaname Tsuzaki, Mitsuhiro Kurita
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Patent number: 6881549Abstract: The present invention provides a method for immobilizing a polysaccharide (PS) to a solid surface, said polysaccharide having a keto-carboxy group (—C(?O)—COOH) or a ketal or hemiketal group corresponding thereto, e.g. derived from KDO (2-keto-3-deoxy-D-manno-octonic acid)), the method comprising the steps of: (a) forming a covalent bond between the carboxy group of the polysaccharide and a reporter molecule (RM), thereby forming a polysaccharide-reporter molecule conjugate (PS-RM), said reporter molecule comprising a recognition/substrate site (e.g. biotin or an anthraquinone); and (b) immobilizing the polysaccharide-report molecule conjugate by forming a specific bond (e.g. by photocoupling or formation of an affinity pair) between the recognition/substrate site of said reporter molecule and a reception/reagent site of the solid surface. The present invention also provides a solid surface thus obtainable and the use of such solid surfaces for diagnostic purposes, e.g.Type: GrantFiled: April 25, 2002Date of Patent: April 19, 2005Assignee: Exiqon A/SInventors: Mogens Havsteen Jakobsen, Ulrik Boas, Eva Irene Stenbaek Jauh, Peter M. H. Heegaard
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Patent number: 6878691Abstract: The present invention discloses compounds of formula I, or pharmaceutically acceptable salts, esters, or prodrugs thereof: which exhibit antibacterial properties. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject in need of antibiotic treatment. The invention also relates to methods of treating a bacterial infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention. The invention further includes process by which to make the compounds of the present invention.Type: GrantFiled: May 5, 2003Date of Patent: April 12, 2005Assignee: Enanta Pharmaceuticals, Inc.Inventors: Yat Sun Or, Guoqiang Wang, Ly Tam Phan, Deqiang Niu, Nha Huu Vo, Yao-Ling Qiu, Yanchun Wang, Marina Busuyek, Ying Hou, Yulin Peng, Heejin Kim, Tongzhu Liu, Jay Judson Farmer, Guoyou Xu
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Patent number: 6875861Abstract: A process for producing nitrosonium ions is described, in which a nitroxyl compound such as TEMPO is oxidized using an oxidizing agent in the presence of a complex of a transition metal such as Mn, Fe, Cu, and a complexing agent such as a polyamine. The process is useful for the oxidation of carbohydrates containing at least 1 cyclic monosaccharide chain group carrying a carbaldehyde group per 100 or per 25 monosaccharide units and per molecule.Type: GrantFiled: February 24, 2000Date of Patent: April 5, 2005Assignee: SCA Hygiene Products Zeist B.V.Inventors: Arie Cornelis Besemer, Jan Matthijs Jetten, Thomas Jaschinski, Ronald Tako Marinus Van Den Dool
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Patent number: 6872707Abstract: The invention relates to halo derivatives of 9a-N-(N?-arylcarbamoyl)- and 9a-N-(N?-arylthiocarbamoyl)-9-deoxo-9a-aza-9a-homoerythromycin A of the general formula (I) wherein R has the meaning of a substituted aryl group of the formula (II) wherein substituents a, b, c, d and e are the same or different and at least one of them has the meaning of halo, a (C1-C6)haloalkyl or a (C1-C6)haloalkoxy group, whereas the remaining ones have the meaning of hydrogen, halo, a (C1-C6)alkyl or a (C1-C6)alkoxy group, and X has the meaning of oxygen or sulfur, and pharmaceutically acceptable addition salts thereof with inorganic or organic acids, to a process for their preparation, to a process for the preparation of pharmaceutical compositions comprising them and to the use of these pharmaceutical compositions for the treatment or prevention of bacterial infections.Type: GrantFiled: May 2, 2000Date of Patent: March 29, 2005Assignee: PLIVA farmaceutska industrija dionicko drustvoInventors: Zorica Maru{hacek over (s)}ic-I{hacek over (s)}tuk, Nedjelko Kujund{hacek over (z)}ić , Gabrijela Kobrehel, Stjepan Mutak, Nata{hacek over (s)}a Mar{hacek over (s)}ić
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Patent number: 6867296Abstract: This invention concerns a process for recovering and purifying dianhydro sugar alcohols from a vapor stream comprising dianhydro sugar alcohols, such as isosorbide, and water vapor.Type: GrantFiled: April 16, 2003Date of Patent: March 15, 2005Assignee: E. I. du Pont de Nemours and CompanyInventor: Kamlesh Kumar Bhatia
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Patent number: 6861512Abstract: The geometric isomers of olefins and olefinic compounds are separated by means of liquid chromatography using a stationary phase comprising an organosilane with a pendant aliphatic functional group such as C18 and a mobile phase which includes an additive comprising alkanes and alkenes.Type: GrantFiled: March 1, 2001Date of Patent: March 1, 2005Assignee: Eisai Co., Ltd.Inventors: Lily Lu, John D. Orr
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Patent number: 6855813Abstract: The invention relates to a process for making Azithromycin crystals using a number of process steps that avoids the use of cumbersome and/or inefficient extraction and/or isolation procedures.Type: GrantFiled: July 19, 2002Date of Patent: February 15, 2005Assignee: Alembic LimitedInventor: Srinivasan Rengaraju
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Patent number: 6852702Abstract: 9a-N-[N?-(phenylsulfonyl)carbamoyl] derivatives of 9-deoxo-9-dihydro-9a-aza-9a-homoerythromycin A and of 5-O-desosaminyl-9-deoxo-9-dihydro-9a-aza-9a-homoerythronolide A and their pharmaceutically acceptable addition salts with inorganic or organic acids are provided, along with a process for their preparation, pharmaceutical compositons, and use in treating bacterial infections.Type: GrantFiled: February 27, 2002Date of Patent: February 8, 2005Assignee: Pliva D.D.Inventors: Nedjeljko Kujundzic, Mirjana Bukvic Krajacic, Miljenko Dumic, Andrea Hasenohrl
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Patent number: RE39087Abstract: A novel form of azithromycin and processes for preparation of pure azithromycin monohydrate isopropanol clathrate (3 molecules of isopropanol for every 10 molecules of azithromycin monohydrate) has been obtained. Preparation of the novel form of azithromycin comprises the steps of dissolving azithromycin in isopropanol, followed by the slow addition of water to the organic solution.Type: GrantFiled: June 5, 2003Date of Patent: May 2, 2006Assignee: Apotex, Inc.Inventors: Khashayar Karimian, Mehrnoush Motamedi
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Patent number: RE39383Abstract: A procedure for preparing 6-O-alkyl erythromycin compounds having the formula: wherein R1 is a loweralkyl group, R2 and R3 an independently hydrogen or a hydroxy-protecting group, except that R2 and R3 may not both be hydrogen simultaneously; Y is oxygen or a specifically substituted oxime; and Z is hydrogen, hydroxy or protected-hydroxy; by reaction of the compound wherein R1 is hydrogen with an alkylating reagent, is the presence of a strong alkali metal base and also in the presence of a weak organic amino base, in a suitable stirred or agitated polar aprotic solvent, or a mixture of such polar aprotic solvents maintained at a reaction temperature and for a period of time sufficient to effect alkyation.Type: GrantFiled: March 22, 2004Date of Patent: November 7, 2006Assignee: Abbott LaboratoriesInventors: Jih-Hua Liu, George A. Foster, Jr., Stephen H. Montgomery
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Patent number: RE39531Abstract: Disclosed are 9-hydrazone erythromycin and 9-azine erythromycin derivatives and the processes for making the same. The compounds are useful intermediates for conversion into 6-O-alkyl erythromycin. Also disclosed are the processes for converting the compounds into 6-O-alkyl erythromycin.Type: GrantFiled: March 5, 2004Date of Patent: March 27, 2007Assignee: Abbott LaboratoriesInventor: David R. Hill
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Patent number: RE39560Abstract: Erythromycin A derivatives represented by the general formula wherein R1 is a 2-alkenyl group having 3 to 15 carbon atoms, an arylmethyl group, or an arylmethyl group substituted by 1 to 3 of a halogen atom, an alkoxy group 1 to 4 carbon atoms, a nitro group or an alkoxycarbonyl group having 2 to 6 carbon atoms, R2 is a substituted silyl group and R3 is a hydrogen atom or R2, are disclosed. These compounds are useful as intermediates of the anti-bacterial agents.Type: GrantFiled: January 28, 2004Date of Patent: April 10, 2007Assignee: Taisho Pharmaceutical Company, Ltd.Inventors: Shigeo Morimoto, Takashi Adachi, Tohru Matsunaga, Masato Kashimura, Yoshiaki Watanabe, Kaoru Sota