Abstract: This invention relates to alkyl and/or alkenyl oligoglycoside isethionates prepared by reacting salts of vinyl sulfonic acid at an elevated temperature and in the presence of basic compounds, with alkyl and/or alkenyl oligoglycosides of the formula (1): R.sup.1 O--(G).sub.p in which R.sup.1 is a straight-chain or branched-chain aliphatic hydrocarbon group with 6 to 22 carbon atoms and 0, 1,2 or 3 double bonds, G is a glycose unit with 5 or 6 carbon atoms, and p is a number between 1 and 10. The products exhibit marked surface-active characteristics and are useful as surfactants.
Abstract: An inhibitor of the biosynthesis of sugar chains containing sialic acid that is excellent in the suppression of inflammation or allergy, which comprises as an active ingredient a sugar compound of the formula (1): ##STR1## wherein R.sup.1 is a hydrogen atom, a substituted or unsubstituted aliphatic hydrocarbon group, a substituted or unsubstituted aromatic hydrocarbon group, a peptide residue or a glycoprotein, and R.sup.2 is a hydrogen atom, a sulfhydryl group, an acyloxy group, an acylthio group, an aryloxy group, an alkyloxy group or a glycothio residue. The inhibitor of the biosynthesis of sugar chains containing sialic acid may be used as a therapeutic agent for inflammation caused by sugar chains containing sialic acid.
Abstract: Cyclodextrin catenanes capable of forming inclusion complexes and a method of preparing them are disclosed. The catenanes comprise one or two per-2,6- di-O-alkyl-.beta.-cyclodextrin macrocycles wherein each per-2,6-di-O-alkyl-.beta.-cyclodextrin macrocycle is interpenetrated by another macrocycle. Such modified cyclodextrins may be used for the electrochemical and optical sensing of small organic molecules, especially small aromatic molecules.
Type:
Grant
Filed:
January 27, 1994
Date of Patent:
August 1, 1995
Assignee:
Eastman Kodak Company
Inventors:
Christopher P. Moore, Trevor J. Wear, James F. Stoddart, Dominique Armspach
Abstract: A cell proliferation matrix consisting of an aqueous gel of hyaluronic acid or a pharmaceutically acceptable salt thereof which is free from production-related animal DNA and RNA and which is in a dissolved state, is disclosed. Further, the use of hyaluronic acid or a pharmaceutically acceptable salt thereof for the preparation of a cell proliferation matrix according to the invention, for the treatment of at least one of bone fractures, Ulcus Varicosum Cruris, and ulcera caused by Diabetes Mellitus and other diseases (e.g. Decubitus) with impaired arterial blood flow, is described. Also, a method of treating at least one of bone fractures, Ulcus Varicosum Cruris, and ulcera caused by Diabetes Mellitus and other diseases with impaired arterial blood flow is disclosed.
Abstract: A process is disclosed for preparing alkyl glycosides of general formula (I), by reacting an alcohol with a reducing sugar or with an equivalent of the latter, in the presence of a binary catalyst formed by a strong organic acid and a weak, also organic, base, having a K.sub.a within the range of from 10.sup.-8 to 10.sup.-1.
Type:
Grant
Filed:
May 7, 1993
Date of Patent:
July 11, 1995
Assignees:
Enichem S.p.A., Eniricerche S.p.A.
Inventors:
Giampietro Borsotti, Claudio Santini, Luigi Nataloni, Tullio Pellizzo
Abstract: New heparin and heparan sulfate derivatives having antithrombotic activity, also endowed with reduced haemorrhagic and anticoagulant activity, are obtained by nucleophilic addition to heparin and heparan sulfate derivatives containing 2,3-anhydrogulonic acid residues. The new products have the formula IV ##STR1## and show a structural modification of the unit of .alpha.-L-iduronic acid 2-O-sulfate with the partial or total selective modification to .alpha.-L-galacturonic acid in which the hydroxyl group in position 3 is replaced with a nucleophilic residue. This structural modification produces an improvement of the biological properties of the heparin and heparan sulfate, substantially keeping the antithrombotic activity while diminishing the haemorragic effect in vivo and the anticoagulant activity in vitro.
Abstract: New heparin and heparan sulfate derivatives having antithrombotic activity, also endowed with reduced haemorrhagic and anticoagulant activity, are obtained by nucleophilic addition to heparin and heparan sulfate derivatives containing 2,3-anhydrogulonic acid residues. The compounds have the formula IV ##STR1## The glycosaminoglycan derivatives obtained through this treatment show a structural modification in the unit of .alpha.-L-iduronic acid 2-O-sulfate with the partial or total selective substitution of the O-sulfate group in position 2 with a nucleophilic residue. The structural modifications produce an improvement of the biological properties of the heparin and heparan sulfate, substantially keeping the antithrombotic activity while diminishing the haemorragic effect in vivo and the anticoagulant activity in vitro.
Abstract: A process for chemically modifying substantially pure xylose-rich oligosaccharides and polysaccharides in homogenous phase solution. The process may be advantageously utilized to produce biodegradable, thermoplastic, melt flowable, low shear resistant and low viscosity xylan derivatives.
Type:
Grant
Filed:
August 6, 1993
Date of Patent:
July 4, 1995
Assignee:
The Center for Innovative Technology
Inventors:
Wolfgang G. Glasser, Rajesh K. Jain, Markku A. Sjostedt
Abstract: Anti-inflammatory compounds are useful, for example, in treating arthritis and heart attack patients. Novel oligosaccharides useful in the rapid synthesis of certain anti-inflammatory compounds are disclosed, as is a rapid method of synthesizing the oligosaccharides. Low pH can loosen the acceptor specificity of galactosyltransferase (lactose synthase: EC 2.4.1.22 ), allowing the rapid synthesis of novel oligosaccharides. The disaccharides cellobiose (.beta.1.fwdarw.4) , laminaribiose (.beta.1.fwdarw.3) , gentiobiose (.beta.1.fwdarw.6) and maltose (.alpha.1.fwdarw.4) acted as acceptors for lactose synthase under low pH conditions. From these four acceptors, the following four novel trisaccharides were synthesized: Gal.sub.p (.beta.1.fwdarw.4)Glc.sub.p (.beta.1.fwdarw.3)-Glc, Gal.sub.p (.beta.1.fwdarw.4)Glc.sub.p (.beta.1.fwdarw.4)-Glc, Gal.sub.p (.beta.1.fwdarw.4)Glc.sub.p (.beta.1.fwdarw.6)-Glc and Gal.sub.p (.beta.1.fwdarw.4)Glc.sub.p (.alpha.1.fwdarw.4)Glc.
Type:
Grant
Filed:
March 31, 1993
Date of Patent:
June 20, 1995
Assignee:
Board of Supervisors of Louisiana State University and Agricultural and Mechanical College
Abstract: The invention relates to the synthesis of 6-deoxykermesates, 6-deoxykermesic acid, and carminic acid, based on a reaction of a 2-halogenonapthazarin with a bis-trimethylsilyl-diene.
Type:
Grant
Filed:
March 17, 1993
Date of Patent:
June 13, 1995
Assignee:
European Colour PLC
Inventors:
John H. P. Tyman, Alberto Fiecchi, deceased
Abstract: N-acyl-N,N'-di-lysogangliosides, N'-acyl-N,N'-di-lysogangliosides and N,N'-diacyl-N,N'-di-lysogangliosides, in which the acyl groups are derived from an organic acid of the aliphatic, aromatic, araliphatic, alicyclic or heterocyclic series and in which at least one of the two acyl groups is not aliphatic, and their preparation are disclosed. Also disclosed is the preparation of the esters, inner esters, amides and hydroxy peracylates of these compounds and salts thereof. These compounds are useful in the treatment of pathologies of the central and peripheral nervous systems.
Abstract: A dermatological pharmaceutical composition for stimulating hair growth and for the treatment of conditions of the skin selected from the group consisting of(a) benign moles, papillomas and seborrheic keratoses;(b) unsightly freckles, pimples and blemishes;(c) stasis dermatitis;(d) dermal ulcers; and(e) fungal nail infections; and(f) gingival and mucous membrane inflammations;the composition comprising an effective amount of tannic acid, a debriding agent and a pharmaceutically acceptable carrier therefore.
Abstract: There is disclosed liquid nutritionals with improved physical stability. The nutritionals are pourable yet able to hold minerals in suspension without sedimentation or sag. The invention comprises the use of iota-carrageenan of a concentration of between 50-1500 parts per million. The nutritional may also comprise kappa carrageenan at a concentration of less than 25% of the total concentration of iota- and kappa-carrageenan. There is further disclosed a method for preparing the liquid nutritional through the use of ultra-high temperature heat treatment.
Type:
Grant
Filed:
May 20, 1994
Date of Patent:
May 16, 1995
Assignee:
Abbott Laboratories
Inventors:
Shie-Ming Hwang, Timothy W. Schenz, James N. Chmura
Abstract: A process for the synthesis of glycosaminoglycans in which one of the .alpha.-L-iduronic-2-O-sulfate acid saccharide units, which is characteristic of glycosaminoglycans with heparin or heparan structure, has undergone a structural modification, entirely or in part, with transformation into .alpha.-L-galacturonic acid substituted in position 3 with nucleophilic groups, is described. The process is carried out by treating glycosaminoglycans having heparin or heparan structure with a nucleophilic reagent in alkaline solution.
Abstract: A process for the synthesis of glycosaminoglycans with heparin or heparan structure modified in position 2 of the .alpha.-L-iduronic-2-O-sulfate acid in which the sulfate group is, entirely or in part, substituted with a nucleophilic group, is described. The process is carried out by treating glycosaminoglycans having heparin or heparan structure with a nucleophilic reagent in alkaline solution.
Abstract: There is provided a process for preparing epoxy-heparide polysaccharides of formula (I): ##STR1## wherein A is a pyran ring with substituents 1 and 4 in the axial position and 5 in the equatorial position, and R and R' are hexosamines which constitute a polysaccharide chain bonded to said ring A by a glucoside, and one of R and R' is H when the ring A is in the terminal position of said polysaccharide chains, and said heparide has a COCH.sub.3 to COOH ratio of 0.5, said process comprisinga) N-desulfation of heparin to obtain the corresponding heparamine;b) acetylation of the heparamine of step (a) to obtain the corresponding heparide;c) epoxidation of the heparide of step (b) by treating the heparide with hydrogen peroxide in an alkaline reaction medium at pH 12-14; andd) cooling the solution obtained in step (c) to a temperature of between 15.degree. and 25.degree. C. and adjusting the pH to between 5.8 and 6.0.
Abstract: Heterogeneous intimate admixtures of sulfated heparinic polysaccharides, well suited for the prophylaxis/treatment of acute thrombotic episodes in a human patient, comprise immixture of sulfated polysaccharides having a weight average molecular weight less than that of heparin and which include from 9% to 20% of polysaccharide chains having a molecular weight less than 2,000 daltons and from 5% to 20% of polysaccharide chains having a molecular weight greater than 8,000 daltons, the ratio between the weight average molecular weight and the number average molecular weight thereof ranging from 1.3 to 1.6.
Abstract: Disclosed are ganglioside GM.sub.3 analogs represented by the formula ##STR1## in which X represents a radical of the following formula ##STR2## wherein at least one of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is hydrogen and the remainder is hydroxyl; ##STR3## wherein at least one of R.sub.5 and R.sub.6 is hydrogen and the remainder is methyl; ##STR4## wherein m is an integer of 15 to 25, l is an integer of 0 to 3, n is an integer of 11 to 15 and Ac represents acetyl. The ganglioside GM.sub.3 analogs are expected to possess an inhibitory activity for influenza virus.
Type:
Grant
Filed:
May 16, 1994
Date of Patent:
January 10, 1995
Assignees:
The Nisshin Oil Mills, Ltd., Akira Hasegawa
Abstract: Highly sulfated oligosaccharides in the form of hexasaccharide and octasaccharide compounds which have antiproliferative activity with respect to smooth muscle cells are useful in treatment of conditions characterized by unwanted smooth muscle cell proliferation such as a result of trauma or disease states such as asthma, congestive heart failure and hypertension. The oligosaccharides have increased ability to inhibit the proliferation of smooth muscle cells and decreased ability to act as an anticoagulant as compared with commercial heparin and/or unseparated fragments of heparin.
Type:
Grant
Filed:
December 28, 1992
Date of Patent:
January 10, 1995
Assignee:
Glycomed, Inc.
Inventors:
H. Edward Conrad, Peter Fugedi, Brian K. Brandley, Lun H. Lam, Roger A. Laine
Abstract: Disclosed are thioglycoside analogs of gangliosides represented by the formula ##STR1## in which Y represents a radical of the following formula ##STR2## and X represents a radical of the formula ##STR3## wherein m is an integer of 15 to 25, l is an integer of 0 to 3 and n is an integer of 11 to 15. The thioglycoside analogs are expected to exert specific enzyme-inhibitory effects.
Type:
Grant
Filed:
February 27, 1992
Date of Patent:
January 10, 1995
Assignees:
The Nisshin Oil Mills, Ltd., Akira Hasegawa