Reacting A Carbohydrate With An Organic -o- Containing Compound (e.g., Reacting Glucose With Methanol, Etc.) Patents (Class 536/18.6)
  • Patent number: 6262029
    Abstract: The present invention is directed to novel bidesmosidic saponin derivatives comprising a triterpene aglycone core substituted at positions 3 and 28 with a monosaccharide or an oligosaccharide which can be the same or different, and having an aldehyde group attached to the core, preferably at the 4-position. The novel derivatives include a lipophilic group that is covalently attached to the 4-position of a fucosyl group that is required in the 28-oligosaccharide substituent. These derivatives preferably have Formula I: wherein Z and R1 to R3 are defined herein. The present invention is also directed to pharmaceutical and veterinary compositions comprising one or more compounds of the present invention. These compositions may be employed as immunopotentiators in animals and humans. The present invention is also directed to methods of making these compounds and to methods of using these compounds as immunostimulating agents and as adjuvants.
    Type: Grant
    Filed: August 13, 1999
    Date of Patent: July 17, 2001
    Assignee: Galenica Pharmaceuticals, Inc.
    Inventors: Jeffery B. Press, Dante J. Marciani
  • Patent number: 6218108
    Abstract: The present invention provides fluorescent nucleosides carrying polycyclic aromatic hydrocarbons such as anthracene, phenanthrene, pyrene stilbene, tetracene or pentacene. The subject nucleosides may be synthesized using a C-glycosidic bond formation method employing organocadmium or organozinc derivatives of the aromatic compounds and coupling with a 1-&agr;-chlororibose or deoxyribose synthon. The &agr;-anomers of the coupling reaction may be epimerized to the &bgr;-anomers by acid-catalyzed equilibration. The fluorescent nucleosides act as DNA or RNA base analogs and can be incorporated into nucleic acids. Resultant fluorescently tagged nucleic acids are useful as probes for target nucleic acids in tissues, solutions or immobilized on membranes.
    Type: Grant
    Filed: May 16, 1997
    Date of Patent: April 17, 2001
    Assignee: Research Corporation Technologies, Inc.
    Inventor: Eric T. Kool
  • Patent number: 6207820
    Abstract: A combinatorial chemical library of compounds structurally related to the moenomycin class of antibiotics has the formula wherein D is a donor mono- or disaccharide, A is an acceptor monosaccharide, and P—R is a lipophosphoglycerate mimetic group. Members of the library have a glycosidic linkage between the anomeric carbon of D and the C2 carbon of A, and the D—A moiety is in turn covalently linked through the anomeric carbon of A to the P—R group. Members of the library exhibit their greatest structural diversity in terms of substitutions occurring at the C3 position of the A residue, substitutions at the C2 position of the D residue, and different P—R groups used in assembling the compounds.
    Type: Grant
    Filed: September 13, 1999
    Date of Patent: March 27, 2001
    Assignee: Incara Research Laboratories
    Inventors: Nigel Mark Allanson, Tin Yau Chan, Nicole T. Hatzenbuhler, Rakesh K. Jain, Ramesh Kakarla, Rui Liang, Dashan Liu, Domingos J. Silva, Michael J. Sofia
  • Patent number: 6204369
    Abstract: A process for preparing alkyl polysaccharides comprising introducing a mixture of a hydrous saccharide in a first portion of fatty alcohol, introducing a second portion of fatty alcohol, agitating the mixture, allowing it to crystallize, reducing water content, contacting the reduced water content dispersion containing solid particles with an effective amount of acid catalyst and reacting the aliphatic alcohol with the saccharide source to form an alkylpolyglycoside.
    Type: Grant
    Filed: June 8, 1999
    Date of Patent: March 20, 2001
    Assignee: Henkel Corporation
    Inventors: C. Deane Roth, Frank L. Edwards, Patrick McCurry, Jr.
  • Patent number: 6194393
    Abstract: 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: Grant
    Filed: January 27, 1998
    Date of Patent: February 27, 2001
    Assignee: The Trustees of Princeton University
    Inventor: Daniel Evan Kahne
  • Patent number: 6184367
    Abstract: The present invention provides a process for the production of two molecules of 4-aryl-2 butanols having the general formula 1 given below: Wherein R═H or glucose from the leaves of Taxus wallichiana, which comprises: (a) defatting air dried, pulverized leaves with aliphatic hydrocarbon solvents, (b) extracting the defatted leaves with chlorinated solvents and polar solvent successively at room temperature, (b) concentrating the chlorinated solvent soluble faction to a residue and treating the residue with aqueous solution of alkali and extracting with chlorinated solvents, (d) acidifying the alkali layer with mineral acid and extracting with ethyl acetate and concentrating the ethyl acetate phase to give compound of formula 1 where R═H, (e) concentrating the polar solvent fraction from step (b) to a residue and treating the residue with aqueous solution of alkali and extracting with chlorinated solvent, and (f) acidifying the alkali phase with mineral acid and extracting wit
    Type: Grant
    Filed: July 21, 1999
    Date of Patent: February 6, 2001
    Assignee: Council of Scientific and Industrial Research
    Inventors: Sunil Kumar Chattopadhyay, Ram Prakash Sharma, Sushil Kumar
  • Patent number: 6184368
    Abstract: Methods for syntheses of polyvalent carbohydrate molecules by glycosylations of partially protected polysaccharides with a single glycosylating agent or a mixture of glycosylating agents(i.e., a combinatorial library) are disclosed. An alternate method utilizes a glycoside, the aglycon of which carries a halogen which can be under strong alkaline conditions linked with a partially protected polysaccharide by an ether linkage. The product of the latter reaction can be subjected to further glycosylation with a single glycosylating agent or a mixture of such agents (=library). The novel resulting polyvalent carbohydrate molecules may be used as antiinfective agents (antibacterial, antiparasital), both for prevention and treatment of diseases, and as agents either for preventing the formation of, or disrupting, biofilms.
    Type: Grant
    Filed: June 28, 1999
    Date of Patent: February 6, 2001
    Inventors: Jiri J. Krepinsky, Niculina Lupescu