Abstract: The present disclosure relates to synthetic mixtures of certain human milk oligosaccharides and uses thereof. Particular mixtures provided herein include: lacto-N-triose II, lacto-N-neotetraose, para-lacto-N-neohexaose, and, optionally, lactose; and lacto-N-triose II, lacto-N-tetraose, para-lacto-N-hexaose II, and, optionally, lactose. These mixtures are useful in the prevention and treatment of viral and bacterial infections.

Abstract: Method for selective 2-sulfation of glycosides.

Abstract: The present invention relates to methods for the synthesis of fondaparinux and intermediates thereto.

Abstract: The invention relates to FGF receptor-activating N-acyl octasaccharides having Formula (I), wherein: R1 is an O-alkyl group optionally replaced by one or more aryl or cycloalkyl groups, R2 is an OSO3? or hydroxyl group, R3 is an alkyl, cycloalkyl, or alkyl-cycloalkyl group, R4 is a disaccharide having Formula (II), R6 is a disaccharide having Formula (III), and R8 is a disaccharide having Formula (IV), where R5, R7, and R9 are OSO3? or hydroxyl groups. The invention further relates to the preparation of said octasaccharides and to the therapeutic use thereof.

Abstract: The present invention relates to a method for preparation of the tetrasaccharide lacto-N-neotetraose (LNnt, formula (I)) especially in large scale, as well as intermediates in the synthesis, a new crystal form (polymorph) of LNnt, and the use thereof in pharmaceutical or nutritional compositions.

Abstract: The present invention provides novel processes for the preparation of Fondaparinux sodium by using the compound of formula ABC5 In some embodiments, the intermediates for the synthesis of Fondaparinux sodium, are also provided.

Abstract: The present invention provides improved processes of preparing Fondaparinux sodium comprising converting a compound of formula ABCDE4 to Fondaparinux sodium at a reaction pH of no more than about 9.0. In some embodiments, the intermediates for the synthesis of Fondaparinux sodium, are also provided.

Abstract: The present invention relates to a chemically modified heparin, with an antifactor II activity of less than 10 IU/mg, an antifactor Xa activity of less than 10 IU/mg and an average molecular weight (Mw) between about 6.5 and 9.5 kDa. Also disclosed is a method of preparing the heparin and its medical use, including treatment of malaria.

Abstract: Method for selective 2-sulfation of glycosides.

Abstract: The invention relates to the FGF receptor-activating oligosaccharides corresponding to formula (I): in which R1 represents an optionally substituted —O-alkyl group, R2 represents a hydroxyl group or an —O-alkyl group, R3, R5, R6, R7 and R8 represent —OSO3? or hydroxyl groups, R4 represents an —NH—CO-alkyl or —O-alkyl group, R represents an —O-alkyl group, and n and m, which may be identical to or different from one another, represent integers equal to 0 or 1. Method for the preparation thereof and therapeutic use thereof are also provided.

Abstract: The invention relates to the use of certain derivatives of D-mannopyranoside for controlling angiogenesis. These compounds have a pro-angiogenic activity, and can particularly be used for preparing a pharmaceutical composition for treating cardiovascular diseases or for treating muscular atrophy. The invention also relates to certain D-mannopyranoside derivatives, to a pharmaceutical or cosmetic composition containing said derivatives, and to the use of such a cosmetic composition for preventing and/or treating hair loss.

Abstract: The present invention relates to novel synthetic polysaccharides with antithrombotic activity, having at least one covalent bond with an amino chain, and to the preparation method thereof and to the therapeutic use thereof.

Abstract: The invention provides a method of identifying biologically active compounds comprising: (a) designing a first library of compounds of formula (1) to scan molecular diversity wherein each compound of the library has at least two pharmacophoric groups R1 to R5 as defined below and wherein compound of the library has same number of pharmacophoric groups; (b) assaying the first library of compounds in one or more biological assay(s); and (c) designing a second library wherein each compound of the second library contains one or more additional pharmacophoric group with respect to the first library; such that the/each component of the first and second library is a compound of formula (1).

Abstract: The present invention relates to a method for preparation of the tetrasaccharide lacto-N-neotetraose (LNnt, formula (I)) especially in large scale, as well as intermediates in the synthesis, a new crystal form (polymorph) of LNnt, and the use thereof in pharmaceutical or nutritional compositions.

Abstract: A galactosamine derivative represented by the following formula (1): wherein R1, R2 and R5 each independently represents SO3? or H, and at least one of them represents SO3?; R3 represents H, acetyl or SO3?; R4 represents H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted acyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group; X represents O, S, NH or CH2; and represents an ? bond or a ? bond, and a sulfotransferase inhibitor comprising the derivative.

Abstract: A process for the preparation of topiramate in an one pot reaction comprises the following steps: A) reacting 2,3:4, 5-bis-O-{1-methylethylidene)-?-D-fructopyranose with sulfurylchloride in xylene in the presence of an organic or inorganic base to form 2,3:4, 5-bis-O-(1-methylethylidene)-?-D-fructopyranose sulfuryl chloride, B) adding a second organic solvent to the mixture obtained in step A) C) reacting the mixture obtained in step B) with ammonia to form topiramate.

Abstract: The invention relates to FGF receptor-activating N-acyl octasaccharides having Formula (I), wherein: R1 is an O-alkyl group optionally replaced by one or more aryl or cycloalkyl groups, R2 is an OSO3? or hydroxyl group, R3 is an alkyl, cycloalkyl, or alkyl-cycloalkyl group, R4 is a disaccharide having Formula (II), R6 is a disaccharide having Formula (III), and R8 is a disaccharide having Formula (IV), where R5, R7, and R9 are OSO3? or hydroxyl groups. The invention further relates to the preparation of said octasaccharides and to the therapeutic use thereof.

Abstract: New compounds and methods for the preparation of combinatorial libraries of potentially biologically active compounds are based on monosaccharides of formula I being a derivative of a furanose or pyranose form of a monosaccharide, .

Abstract: The present invention is directed to new therapeutic compounds isolated from spider venom and methods of using these new compounds. The compounds are sulfated nucleoside derivatives including ribonucleoside mono- and disulfates derived from guanine, adenosine, and cytidine. Some of these compounds are glycosylated or fucosylated bearing one or more sugar residues.

Abstract: The present invention relates to new morphine-6-glucuronide derivatives, to pharmaceutical compositions thereof and uses thereof.

Abstract: The present invention relates to novel synthetic polysaccharides with antithrombotic activity, having at least one covalent bond with an amino chain, and to the preparation method thereof and to the therapeutic use thereof.

Abstract: Procedure for the synthesis of deprotected pentasaccharides from a protected precursor pentasaccharide through a reaction procedure having five stages whereamong is included an N-sulphation of amino groups and a hydrogenolysis of benzyl groups. Through this procedure a drastic reduction is achieved in the total synthesis time in comparison with the process traditionally employed, together with increased reproducibility thereof, permitting the standardisation thereof.

Abstract: Method for selective 2-sulfation of glycosides.

Abstract: The present invention relates to novel synthetic hexadecasaccharides with antithrombotic activity, having at least one covalent bond with an amino chain, and to the preparation method thereof and to the therapeutic use thereof.

Abstract: Methods are described for the preparation of combinatorial libraries of potentially biologically active disaccharide compounds. These compounds are variously functionalized, with a view to varying lipid solubility size, function an other properties, with the particular aim of discovering novel drug or drug-like compounds, or compounds with useful properties. The invention provides intermediates, processes and synthetic strategies for the solution or solid phase synthesis of disaccharides, variously functionalized about the sugar ring, including the addition of aromaticity and charge, and the placement of pharmaceutically useful groups and isosteres.

Abstract: Processes for the synthesis of the Factor Xa anticoagulent Fondaparinux, and related compounds are described. Also described are protected pentasaccharide intermediates as well as efficient and scalable processes for the industrial scale production of Fondaparinux sodium by conversion of the protected pentasaccharide intermediates via a sequence of deprotection and sulfonation reactions.

Abstract: The present invention describes novel methods of identifying compounds which inhibit HIV particle formation and Rev-dependent HIV production. The present invention also provides methods and compounds for inhibiting HIV particle formation and or treating patients infected with HIV.

Abstract: The core structure of pentaerythritol has been used as a replacement for one or both sugars in lipid A, leading to the generation of a series of lipid A analogs. These lipid A analogs may further differ from lipid A with respect to, e.g., the number, nature and location of negatively charged groups, and the number, nature and location of the lipid chains. The lipid A analogs may be lipid A agonists useful as immunostimulatory agents, or lipid A antagonists useful in the treatment of septic shock. In a like manner, a residue of pentaerythritylamine may be used as a replacement for an amino sugar residue in a carbohydrate ligand having a biological activity of interest, generating a series of ligand analogs. These are useful, e.g., as haptens, inhibitors of bacterial-host cell adhesion, etc.

Abstract: The invention relates to substituted fluoroglycoside derivatives of pyrazoles of formula (I) as further defined in the specification, to the physiologically compatible salts thereof, to a method for their production, and to their use as antidiabetics.

Abstract: The present invention relates to pentose and pentose derivatives that are effective at increasing glucose transport in a non-insulin dependent manner, and to uses thereof for a) treating and/or preventing hyperglycemia; b) treating and/or preventing the complications of hyperglycemia; c) treating diabetes; d) increasing the rate of cellular glucose transport; e) increasing the rate of cellular glucose uptake; f) improving the ability of a subject to metabolize glucose; g) treating daily blood glucose fluctuations; h) reducing blood sugar levels; i) reducing the dosage of anti-diabetic medication needed for treatment of diabetes. The present invention further provides novel pentose derivatives having beneficial properties in terms of pharmacokinetics, to pharmaceutical compositions comprising these novel compounds and uses thereof.

Abstract: The present invention relates to monosaccharide derivatives as anti-inflammatory agents. The compounds disclosed herein can be useful for inhibition and prevention of inflammation and associated pathologies including inflammatory and autoimmune diseases such as bronchial asthma, rheumatoid arthritis, type I diabetes, multiple sclerosis, allograft rejection, psoriasis, inflammatory bowel disease, ulcerative colitis, acne, atherosclerosis, cancer, pruritis and allergic rhinitis. Pharmacological compositions containing compounds disclosed herein and the methods of treating bronchial asthma, chronic obstructive pulmonary disease, rheumatoid arthritis, multiple sclerosis, type I diabetes, psoriasis, allograft rejection, inflammatory bowel disease, ulcerative colitis, acne, atherosclerosis, cancer, pruritis, allergic rhinitis and other inflammatory and/or autoimmune disorders, using the compounds are also provided.

Abstract: Compounds and methods are provided for modulating in vitro and in vivo processes mediated by selectin binding. More specifically, selectin modulators and their use are described, wherein the selectin modulators that modulate (e.g., inhibit or enhance) a selectin-mediated function comprise a class of compounds termed BASAs (Benzyl Amino Sulfonic Acids, which include a portion or analogue thereof linked to a carbohydrate or glycomimetic.

Abstract: A cocrystal of (1S)-1,5-anhydro-1-[3-(1-benzothien-2-ylmethyl)-4-fluorophenyl]-D-glucitol and L-proline. It is a cocrystal of known compound A, which has a constant quality, is superior in storage stability, has no moisture absorptivity, and is suitable as a crystal of a drug substance used for preparing pharmaceuticals.

Abstract: The present invention provides glucopyranosyloxybenzylbenzene derivatives represented by the general formula: wherein P represents a hydrogen atom or a group forming a prodrug; R1 represents a hydrogen atom, an optionally substituted amino group, a carbamoyl group, an optionally substituted lower alkyl group, an optionally substituted lower alkoxy group, etc.; R2 represents a hydrogen atom or a lower alkyl group; and R3 represents an optionally substituted lower alkyl group, an optionally substituted lower alkoxy group, an optionally substituted lower alkylthio group, etc., which have an improved oral absorption, and exert an inhibitory activity in human SGLT2, and therefore are useful as drugs for the prevention or treatment of a disease associated with hyperglycemia such as diabetes, diabetic complications or obesity, or pharmaceutically acceptable salts thereof, and pharmaceutical uses thereof.

Abstract: Novel carbohydrate-based compounds with an attached ring system that have antimicrobial or cytostatic activity. The compounds are administered to humans and animals for the treatment or amelioration of bacterial, fungal, viral or protozoal infections or tumors.

Abstract: The present invention provides compounds having the formula: wherein A is chosen from a nitrogen-, oxygen-, or sulfur-linked aryl, alkyl, cyclic, or heterocyclic group; both B and C are hydrogen, or either B or C is a halogen, amino, or thiol group and the other of B or C is hydrogen; and D is a primary alcohol, a hydrogen, or an oxygen, nitrogen, carbon, or sulfur linked to phosphate, a phosphoryl group, a pyrophosphoryl group, or adenosine monophosphate through a phosphodiester or carbon-, nitrogen-, or sulfur-substituted phosphodiester bridge, or to adenosine diphosphate through a phosphodiester or carbon-, nitrogen-, or sulfur-substituted pyrophosphodiester bridge. The present invention also provides pharmaceutical compositions containing the above compounds, methods of using the above compounds as pharmaceuticals, and processes for preparing the above compounds.

Abstract: The invention relates to novel 5-thioxylose compounds, preferably derivatives of the 5-thioxylopyranose type, to the method for their preparation and to their use as active principles of drugs intended especially for the treatment or prevention of thromboses or cardiac insufficiency.

Abstract: The present invention relates to monosaccharide derivatives as anti-inflammatory agents. The compounds disclosed herein can be useful for inhibition and prevention of inflammation and associated pathologies including inflammatory, cancer, cardiovascular and autoimmune diseases such as bronchial asthma, rheumatoid arthritis, type-I diabetes, multiple sclerosis, allograft rejection, psoriasis, inflammatory bowel disease, ulcerative colitis, acne, atherosclerosis, pruritis or allergic rhinitis. Pharmacological compositions containing compounds disclosed herein and the methods of treating diseases such as bronchial asthma, rheumatoid arthritis, type-I diabetes, multiple sclerosis, cancer, cardiovascular diseases, allograft rejection, psoriasis, inflammatory bowel disease, ulcerative colitis, acne, atherosclerosis, pruritis or allergic rhinitis and other inflammatory and/or autoimmune disorders, using the compounds are also provided.

Abstract: Method for the production of C-aryl glucoside SGLT2 inhibitors useful for the treatment of diabetes and related diseases. and intermediates thereof. The C-aryl glucosides may be complexed with amino acid complex forming reagents.

Abstract: The invention relates to novel derivatives of morphine-6-glucuronide, the preparation method thereof and the uses of same in therapy, for example, as analgesics.

Abstract: The present invention relates to aminoglycoside compounds having antibiotic activity. Moreover, the present invention relates to L-aminoglycoside compounds and diastereomers thereof which posses antibiotic activity and are not susceptible to development of resistant bacterial strains. The present invention also relates to methods of treatment and pharmaceutical compositions that utilize or comprise one or more of aminoglycoside compounds provided by the invention.

Abstract: The present invention provides aminoglycosides and pharmaceutical compositions that include the aminoglycosides. The aminogylcosides are useful to treat or prevent infectious diseases (e.g., bacterial infections) in a mammal (e.g., human).

Abstract: This invention provides compounds containing a 2-deoxy-2-amino-?-D-glucopyranose (glucosamine) glycosidically linked to a cyclic aminoalkyl (aglycon) group. The invention further provides methods for inducing an immune response using the compounds of the present invention in the presence or absence of an antigen. In addition, methods for treating disease with the compounds of the present invention with or without an antigen are also provided in this invention.

Abstract: Compounds and methods are provided for modulating in vitro and in vivo processes mediated by selectin binding. More specifically, selectin modulators and their use are described, wherein the selectin modulators that modulate (e.g., inhibit or enhance) a selectin-mediated function comprise a class of compounds termed BASAs (Benzyl Amino Sulfonic Acids, which include a portion or analogue thereof) linked to a carbohydrate or glycomimetic.

Abstract: 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.

Abstract: 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.

Abstract: Methods and compositions for treating or ameliorating diseases and other conditions, such as infectious diseases, autoimmune diseases and allergies are provided. The methods employ cyclic AGPs for selectively stimulating immune responses in animals and plants.

Abstract: Highly hydrophilic indole and benzoindole derivatives that absorb and fluoresce in the visible region of light are disclosed. These compounds are useful for physiological and organ function monitoring. Particularly, the molecules of the invention are useful for optical diagnosis of renal and cardiac diseases and for estimation of blood volume in vivo.

Abstract: The present invention relates to compounds of the formula (I), wherein R is independently SO3? or CH3; the spacer is a flexible spacer of a length of 13-25 atoms; the charge of the pentasaccharide residue is compensated by positively charged counterions; and the total number of sulfate groups in the pentasaccharide residue is 4, 5 or 6; or a pharmaceutically acceptable salt, a prodrug or a solvate thereof. The compounds of the invention have antithrombotic activity and can be used in treating or preventing thrombin-related diseases.

Abstract: Sugar-modified SIN-1 compositions are provided. The compositions are useful for generating NO in response to hydrolytic activity of a glycosidase specific for the O-glycosidic bond between the sugar and SIN-1 moieties. Pharmaceutical compositions containing the sugar-modified SIN-1 compositions and methods of using the compositions are also provided.