Process for preparing derivatives of muramyl peptide antigens

专利摘要:
Die Erfindung betrifft neue Antigenderivate bestehend aus einem Antigen und mindestens einem damit, gegebenenfalls über ein Brückenglied, kovalent verbundenem Muramyl-peptid, pharmazeutische Prsparate enthaltend solche Verbindungen und Ihre Verwendung als Impfstoff. Die neuen Antigenderivate bringen eine ausgeprsgte Steigerung der Immunsntwort auf das Antigen, insbesondere auch eine zellvermittelte Immunität unter klinisch akzeptablen Verabreichungsbedingungen.
公开号:SU1055312A3
申请号:SU792739298
申请日:1979-02-23
公开日:1983-11-15
发明作者:Башанг Герхард；Макс Дитрих Феликс；Гизлер Роланд；Хартманн Альберт；Станек Ярослав；Тарчай Лайос
申请人:Циба-Гейги Аг (Фирма)；
IPC主号:

专利说明:

characterized in that the antigen is condensed with a 5-150-fold excess of murapylpeptide of formula (II) bound to Z, which has the indicated meanings, wherein the fragment 1 muramylpeptide contains a carboxyl group or an activated ester of a carboxylic acid and the antigen contains amino oxyl or mercapto group, or the Z-linked muramyl peptide contains a free amino group and an antigen with at least one free carboxyl or activated ester group of carboxylic acid s, at a temperature in water or aqueous buffer at pH 5-9 in -techenie time from 5 minutes to 48 hours, by the method
activated esters or carbd; -limid method.
Priority by p p v z a a m:
02.27.78. in case of compound forms, uly (I), where A is serum albumine, erythrocyte membranes, polysaccharides, Neisseria meningitldis cures, merozoite of malaria pathogens, T-lymphoblus-1
04/07/78. with compounds of Forgmula (I), where A is cancer cells of the gland, vaccine against scur, rabies vaccine, antigens of the virus against influenza
05/18/78. with compounds of formula (I), where A is tetanus and cholera current of soybean, eicosapeptide, or parasites of Tripanosoma cru2i.
This invention relates to a process for the preparation of new biologically active derivatives of muramyl peptidantigenes, which can be used in medicine. ,
In peptide chemistry, condensation of fragments containing an amine group and a carboxyl group is widely used by the method carbodiimide and activated esters ij
The purpose of the invention is a method of obtaining new biologically active compounds - derivatives of muramyl peptide antigens with valuable pharmaco logical properties. .
This goal is achieved by the fact that according to the method of poly5gc, no derivatives of muramyl peptide antigens of the formula:
and - z -, (I)
where A is the antigen residue: serum albumin, erythrocyte membranes, Neissejria meningi tidis polysaccharide, me9 agents of malaria pathogens. T-limfoblasts, breast cancer cells, vaccine against scur, rabies, influenza virus antigens, tetanus and cholera toxoids, eicosapeptide, parasites Tri panosoma cruzi, Z O (which corresponds to the direct link between the antigen and the muramyl peptide), the rest bound to the nitrogen atom eC,
-diaminoalkane () candicarbonyl () or OL-, p- or y -aminoalkancar bon la (Cr-7) / „
Mr - residue muramylpeptida formula
CHzORj
de X carbonyl-, carbonyloxylyl sulfonyl group; ., Cd and R - hydrogen or trimethylsilyl ;; .R is phenyl, unsubstituted lower alkyl or lower alkyl, substituted by hydroxyl, carboxyl or ghkoxycarbonyl (C) a, Rg, R "and Rfj is hydrogen or alkyl;
R- - water |) od, C —C-alkyl, free, esterified into ester or ester C;) —C-oxyalkyl, free esterified into ester or ester of С | C; (-C C-amioalkyl, chloromethyl, phenyl, benzyl or And -oxybenzyl; X, R | jj and Rj - independently of
another free esterified ester or amidated carboxyl; Rjg -, also hydrogen, p - is an integer higher than 0 on condition that 1 mg or 10 antigen cells respectively contain from 0.01 d 0.5 kg of muramyl peptide in compounds of formula (D), the antigen is condensed with 5 -150-fold with an excess of the muramylpeptide of formula (It is associated with Z having the indicated (Values, moreover, the Y fragment is linked with the Z fragment Yuramyl peptide contains a carboxylic group or an activated carboxylic ester group, the antigen contains at least one free amino, hydroxy) or a mercapto group, or a fragment Z linked muramyl peptide with keeps free amino group and antigen with at least one free carboxylic or activated carboxylic ester group, at a temperature in water or aqueous buffer at pH 5-9 for a time from 5 minutes to 48 hours by the method of activated esters or by the carbodiimide method. compounds cause an increase in the immune response to an antigen, a cell-mediated immunity under clinically acceptable conditions of administration, as shown in biological trials Potentiation manifested through In vivo immunity of cells of cells: increased Spattyp sensitivity against serum bovine albumin (BSA) and against sheep erythrocytes (SRBC) in guinea pigs. Pirbrignt guinea pigs are immunized for 1 day with 1 mg BSA or 1 mg SRBC - Ghosts (SRBCG) and. Freund's complete auxiliary agent by injecting a mixture of antigen and auxiliary agent into both hind legs. After 3 weeks, a skin reaction is induced by intradermal injection of 100 μg VA or μg SRBCC in 0.1 ml of buffered physiological saline and 24 hours after that, the reaction volume is determined, which is calculated from the erythema rate and the increase in skin thickness. The specific antigenic increase in reaction volume observed after 24 hours (Spattyp reaction) serves as a measure manifested by immunity cells. BSA and SRBCC are weak immunogens so that they can be pure ... or in an oil-water emulsion with Freund's incomplete adjuvant (10. BSA-hamster, respectively, SHBCG suspension in 0.9% Nas, mixed with. 8.5 h. Ba, woo F and 1.5 h. Arfacei A induces the Spattyp reaction, and for effective immunization should be applied in a complete auxiliary agent, to which mycobacterium is added (5 mg of the dead and 10 ml lyophilized M. Ba-, yo F / ArCacef A),, Instead of mycobacteria, new compounds containing as a BSA antigen (1 mg BSA, 60 µg MDP per animal a) or SRBCG (1 mg RBCG, 25 µg MDP per animal) is used in suspension either as an antigen-oil mixture or in carboxymethyl cellulose (CMC). The new compounds in the absence of mycobacteria are induced by the described Spattyp reaction. Spattyp reactions against BSA and against SRBCG can also be achieved by the fact that new compounds are not mixed in the complete Freund auxiliary agent, but are suspended and used in CMC. Especially effective in this case is inside, muscle administration. Under these conditions, an equal amount of free Muramyl Peptide, industrial to CMC, is significantly less active compared to a new biologically active substance. Thus, new compounds with clinically acceptable us-i catch use, i.e. when administered with concomitant substances, they are able to induce cell-mediated immunity against soluble protein antigens. Potentiation of cell-mediated in vi-r vo immunity: an increase in Sp & ttyp immunity against BSA and against SRBCG in mice. Male MAG mice are immunized on Day O with partial doses of the antigen that is not linked to muramyl peptide. (BBA-agarose or SPBCG) or associated with it (BSA-agarose or SRBCG). The BSA-agarose preparation is administered subcutaneously in doses ranging from 0.1 to 100 µg (per case; a new compound with muramyl pepid) corresponds to the dose of the biologically active substance 0.0029-6 µg per animal) in 0.2 ml of buffered saline salt.SRBCG drug at a dose of 0.013 mg (in the case of a new compound with muramylpeptide corresponds to the dose of the biologically active substance .0.25-75 µg per animal) in 0.5 ml of buffered saline saline is administered intraperitoneally or 0.5 MP intracutaneously, respectively, in the foot of 3 paws. After 4–20 days, a Spattyp reaction is induced by injecting 100 µg BSA or lOi SRBG into 20 µl of buffer saline in a squint of the hind foot and, after 24 and 48 hours, determine the reaction volume, which is calculated from the swelling of the foot. The observed specific antigenic increase in foot volume serves as a measure of the manifestation of cells through immunity cells. On the 14th day after immunization with compound B $ L-agarose-MOR, SijSttyp-r. Pronounced reaction occurs even in the case of very small doses (0.1 μg, respectively, 0.006 μg of biologically active substance). In contrast, free BSA agarose is not able to sensitize the SpattYp reaction. Similarly, SRBCG-MDP compounds, especially after intradermal administration, are able to induce a reaction that is much more pronounced than the reaction that occurs ( after sensitization of SRBCG, not in association with muramyl peptide. Thus, new compounds can also significantly enhance cellular immunity. Potentiation of humoral immunity in vivo: increased reproduction of antibodies against BSA in mice. NMRI is deduced by intraperitoneal injection of 0.1-100 μg of BSA associated with muramylpeptide (0.0014 b, About μg of biologically active substance), 10, 17 and 28 days later, serum samples are collected and tested for anti-BSA antibodies Passive Haemaggfutancies Techniques. In doses administered, free BSA is a weak immuno gene for experimental animals, i.e. it is unable or capable of causing only a small amount of antibody production. The connection of BSA with muramylpeptide allows an increase in serum antibody titer by a factor of 2–3 (titer is the sum of the Gegj titer difference in three days of blood). In addition, new compounds that are also coupled to agarose as a carrier, after intraperitoneal or subcutaneous administration, are even more potent. experiments show that the proposed new compounds can also significantly increase the humoral immunity. The described antigen derivatives are new-type vaccines or improved known vaccines and serve for new vaccination methods or for simplifying traditional vaccination methods (for example, the amount of vaccinations that are needed to maintain protection for a prolonged period of time can be reduced. Example 1. To a solution of 1 g of bovine serum albumin in 100 ml of a 0.1 M sodium carbonate solution and a 0.5 M sodium chloride solution, 500 mg of 2-acetamido-3-0- {i-1- (0 -1-carbamoyl-3-succinimidooxycarbonylpropyl) -carbamoyl ethyl -carbamoylmethyl -2-deoxy-B-glucose. The solution is stirred for 4 hours at room temperature and immediately after that the reaction mixture is filtered under sterile conditions (MFMiEipore, 0.45 µm filter). Conjugated bovine serum albumin is separated by means of dialysis filtration through Ilter Amikon im-10 from low molecular weight reaction products and salts and subjected to freeze-drying. The quantitative determination of muramyl peptide bound to bovine serum albumin is carried out using a Morgan-Elson reaction. On average, 60 µg of muramyl peptide was found per 1 mg of the compound with bovine serum albumin. The succinimido ester, which is used as a starting material, can be obtained, for example, by the following method. 1 mmol 2-acetamido-3-0- {L-1- (1 -1-carbamoyl-3-carboxypropyl) -carbamoylethyl-carbamoyl methyl 2-deoxy-D-glucose, 1 mmol dicyclohexycarbodiimide and 1.1 mmol N-oxysuccinimide dissolved in 3 ml of absolute dimethylformamide and in a closed vessel under conditions that exclude the presence of moisture, the reaction mass is stirred for 20 h. The precipitated dicyclohexyl urea is separated, the solvent is evaporated under high vacuum, the resulting residue is treated with diethyl ether, then it is filtered and dried. The succinimidosphyre obtained by this method can be stored under conditions that exclude the presence of moisture, for example, in a vial filled with nitrogen. Example 2: When an antigen-derived agarose derivative obtained in Example 1 is condensed, an agarose derivative B10-RAD Affi-Ge 10 is marketed. It contains an ether-like side chain (Spacer arms) N-alkylsuccinimide on the agarose frame, which is esterified with N- - oxysuccinimide. 120 mg of bovine serum albumin derivative obtained in accordance with Example 1 is dissolved at 4 ° C.
in 12.5 ml of 0.1 M phosphate buffer solution with pH 7, 3. Then, 500 mg of Affi-GeC 10 is suspended in the solution by shaking, after which time the mass is shaken for an additional 4 hours at. The remaining active ester groups are reacted by treating for 30 min with 1 M solution of ethanolamine hydrochloride in 0.1 M phosphate buffer (pH 7.3). After this, the gel is placed in a column and first a 200 solution is eluted with a concentration of 0.1 M phosphate buffer and 1 M sodium chloride (pH 7.3) and then 20 ml of physiological saline solution. Determining the amount of the compound muramylpeptide and bovine serum albumin that is added as a result of condensation to Affi-GeE 10 is performed by quantitative analysis of the content of bovine serum albumin and amino acids in the hydrolyzate of a certain aliquot portion of the gel. On average, 9–10 mg of muramylpeptide derivative and bovine serum albumin per 1 ml of swollen Affi-GeE 10 were detected.
Example 3. Sheep erythrocyte membranes are obtained from fresh sheep blood. To a suspension of 500 ml of sheep erythrocyte membranes in 50 ml of a solution, with concentrations of 0.1 M sodium carbonate and 0.1 M sodium chloride, 400 mg of 2-acetamido-3-0- {l-1- (0 , -1-carbamoyl-3-succinimido-oxycarboylpropyl) -carbamoylethyl-carbamyl-methyl. -2-deoxy-O-glucose and the mixture is stirred for 4 h 1 at room temperature. After that, the product interacts with the membranes e | The i-thromocytes are sedimented by treating the mixture for 1 hour in an ultracentrifuge at 90000 and 4 ° C. The precipitate obtained is washed three times with a buffer solution of phosphate and sodium chloride, the suspension is suspended each time, in which the pacTBopejj is then separated in an ultradrifuge and then washed once distilled water. The washed compound with erythrocyte membrane is suspended in 100 ml of distilled water and freeze dried.
The quantitative determination of the muramyl peptide associated with sheep erythrocytes is carried out using the Morhon El Elson reaction, as a result of which 25 µg of muramyl peptide is detected per 1 mg of erythrocyte membranes.
Note 4. 4 1UO mg group C
polysaccharide Ncisserla meningltldls
and 110 mg (0.2 mmol) of hydrochloride
; 2-acetamido-3-0 -1 -1 (0-1-carbamoyl-3-M-amino ethylcarbamoylpropyl) -carbamoyl ethyl 3-carbamoylmethyl; 2-deoxy-D-glucose is dissolved in 10 ml of distilled water and the pH of the solution is adjusted to 5 by adding dilute hydrochloric acid.
19.2 mg of 1-ethyl-3- (3-dimethylaminopropyl) -carbodiimide hydrochloride are added to the solution with stirring. The mixture was stirred for 1 hour at room temperature, the pH of the mixture was adjusted to 5 by adding dilute sodium hydroxide solution, after which 5 ml of 2 M sodium acetate buffer solution (pH 5) was added and the reaction mixture was stirred for 30 minutes. Immediately thereafter, the pH of the mixture was adjusted to 7 by the addition of sodium hydroxide. The solution is filtered, under sterile conditions, the filtrate is dialyzed against distilled water at and immediately after this, sublimation, and dried.
The quantitative determination of desmethylmuramyl dipeptide attached to the c-polysaccharide is made by analogy with example 1 using the Morgan-Elson reaction, as a result of which 80 µg of desmethylmuramyl dipeptide per mg of polysaccharide are found.
Apply 2-ace "amino-3-0- (L-1-tp-l-carbamoyl-3-N-amino-egilcarbamoylpropyl) -carbamoylethyl3 -methyl -2-deoxy-E -glucose hydrochloride 2-acetamide-3-deoxy-E-glucose, for example, to follow; (im way.
1 mmol 2 acetamino-3-0-CL-1- (D-1-carbamoyl-3-carboxypropyl) -carbamoyl ethyl 3 -carbamoylmethyl -2-deoxy-O-glucose and 2 mmol of K-ethyl-m- (3-dimethylaminopropyl hydrochloride ) - 1 -carbodiimide is dissolved in 10 ml of Bof and the solution is adjusted to pH 5.0 by adding hydrochloric acid, after which a solution of 5 mmol of ethylene diamine dihydrochloride in 10 ml of water is added. The reaction mixture at pH 5.0 and room temperature is stirred for 6 hours, then placed in a column filled with weakly acidic Amberlite CG 50 nf cation exchanger, the column having a size of 2.5 x 45 cm and elution with a 0.05 M solution pyridium acetate (pH 3.7, 300 ml). Containing the resulting acetate 2-acetamino-Z-O-Tb-1- (D-l-carbamate-3-N-aminbethyl-cyrbamoyl-prspil) -carbamoylethyl | -carbamoylmethyl-2-deoxy-0-glucose fractions are tested and characterized using / ninhydrin or high-voltage electrophoresis, freeze-dried.
The conversion of the product into the hydrochloride form is carried out as follows. Lyophilisate is dissolved in 6 ml of 0.2N. hydrochloric acid solution and chromatography on BlO-Ge | P2-column dimensions 2.5 ") t90 cm when using water as an eluent. The fractions containing 2-acetamino-3-0- (L-1- (L-1-carbamoyl-3-Y-amino-ethyl-carbamoyl-propyl) -carbamoyl-ethyl-carbamoyl-methyl-1-2-dveoxy-O-glucose hydrochloride are freeze-dried. According to electrophoresis with high voltage, the resulting product is homogeneous. When determining the composition of the hydrolyzate, the molecular ratio of 1 muraminic acid: 1L-alanine: 1D-glutamic acid: ethylenediamine was found. When using the corresponding muramyl dipeptides as starting compounds, the corresponding hydrochloride is obtained in a similar way S-Aminoethyl fttda, namely 2-ace.amino-3 0-Drlr- {Lrl- (D-1-carbamoyl-3-N-aminoethyl-arbamoylpropyl) -arbamoylethyl hydrochloride; 0-carbamoyl ethide-2-deoxy-1b glucose, hydrochloride 2 - benzosch1amino-3-0- {K-1-G1-1- {0-1-k arbamoyl-3-N-gminoethi carbamoyl drank) -carbamoylethyl-carbamoylethyl-2-deoxy-O-gluc6zy, 2-benzoylamino-3-0- {l-1- (Dl-carp molo-3-N-aminoethylnarbamoylpropol) -carbamoylethyl-carbamoylmethyl | -2-deoxy-O-glucose hydrochloride, 2 acetamino-3-0- hydrochloride 1- (B-1-N-carbamoyl methylcarbamoyl-3-N- amine methyl ethylcarbamoylpropyl) -carbamoylethyl} -carbamoi, methyl, -2-deoxy and-D-glucose, chloride gndrohl 2-benzoylamino-3-0- Ll (l-kapbamoil Tl-3-N-propyl aminostidkapbamoill) -karbamoilpropil7-karbamoilmotilj -2-deoxy-O-glucose hydrochloride 2-propionylamino-3- 0- {{jj-1- - (O-1-carbamoyl-3-K-amino-ethylate carbamoylpropyl) -carbamoylethyl 3 -carvamoyl Methyl -2-deoxy-O-glucose, gdro chloride 2-acetyl but-3-0- {b- 1- (D-1 -carbamoyl-3-N-aminoethylcarbamoylpropyl) -carbamoylpropyl 3-carbamoyl methyl-2-deoxy-0-gluco-9, 2-acetylamino-3-O-f Ll hydrochloride (D-1 carbamoyl-3-A-amino-tetracarbamide-3-O-f Ll (D-1carbamoyl-3-I-aminoethylcarbamoyl 3-O-f Ll (D-1carbamoyl-3-I-amino-carboxymethyl-3-O-f Ll-D) ) -carbamoyl-2-hydroxyethyl -carba mymethyl -2-deoxy-0-glu ose, hydrochloride id-propionylgilino-3-0-L-1- (or 3-carboxy-3- or 1-K-aminoethI | Lcarbamoyl propyl) -carba myethyl-carbamoylethyl -2-deoxy-D-glucose, 2-benoylglycl o-3 hydrochloride -0- {ъ-1- (0-1-carbamoylmethylcar bamoyl-3-N-aminoethylcarbg Moylpropyl-carbamoylzil-carbamoylmethyl-2-deoxy-O-glucose, 2-acetamino-3-0- hydrochloride | L-1- (D-1-carbamoyl-Z-N-amio-ethylcarbamoylpropyl) -carbamoid-2-methylpropyl1 | -carbamoylmethyl -2-deoxy-O-glucose, hydrochloride 2-acetamino-3-0-1 -1-L-1- {B-1-carbamoyl-3- (1-K-aminoethylcarbamoyl) -ethylcarbamoylpropyl) -carbamoylethyl3 - carbamoyl ethyl 5-2 deoxy-0-glucose, 2-acetamino-3-0-1-1 -: (hydrochloride; P-1-carboxy-3-N-aminoethyl-rbamoylpropyl) -carbamoyl-2-methylpropyl-carbamoylmethyl -2-deoxy -P-glucose, 2-acetamino-3-0-L-1- (D-l-carbamoyl-3-K-aminoethylcarbamoylpropyl) -carbamoyl-N, N-tetramethi-3-deoxycaroanoylmethyl-4-2-deoxy-p-gl-1-boxy hydrochloride , hydrochloride 2-acetamino-3-0-Ll- (DI-carpamoyl-3-N-amino-ethylcarbamoyl-propyl) -carbamoyl ethyl 3 -N-I ylcarbamoylmethyl -2-deoxy-PG of yukoz or 2-benzoylamino-3-0-i.-1- (0-1-carbamoyl-3-Y-aminoethylcarbamoylpropyl) -carbamoyl-2-methylpropyl 3 -carbamoylmethyl-2-deoxy hydrochloride .i-0- -glucose. These compounds can be introduced into a condensation reaction with a group C of polysaccharides. Example 5. Immediately after receiving the merozoites of the Pfasmodium malaria pathogen. (The total yield of Pheus-monkey infected blood is suspended in a solution of 100 mg, i.e. 0.17 mmol) 2-acetamine-3-0-f Ll- (Dl-carbamoyl-3-cyccinimide docicicarbonyl propyl-carbamoyl ethyl carbamoylmethyl 5 -2-deoxy-Og yukoza in 15 ml of physiological buffer solution (pH 7.2). Suspension is kept for 1 hour at 37 s. Then the reaction product is sedimented by means of cement1) and arc extrusion. The resulting precipitate is washed by suspending in a fever buffer solution and centrifuged again. The permeable compound with merozoites according to G.Kh. Mitchel is suspended in a 10% bottle of Phe susobesin and freeze-dried. . . The quantitative determination of muramyldipeptide bound to merozoites was made using the Morgia-Elson reaction, with the result that 40-60 µg of muramyl dipeptide was detected per 1 mg of merozoites. Example 6. In a solution of 200 mg (0.34 mmo) of 2-acetamino-3-0-LI- (L-1-carbamoyl-3-succinimidooxycarbonylpropyl) -carbamoylethyl 3 -carbamoylmethyl-1-2-deoxy-0-glucose in 20 ml phosphate buffer physiological saline solution (pH 7.2) is suspended with 10 T-lymphoblasts CBA / J mya (T-lymphoblasts are prepared in mixed eymphocyte cutiere against stimulating cells of C57BL / 6 mice). After that, the obtained Compound with lymphoblasts is sedimented: by centrifugal erosion, after which the precipitate is washed
suspended in phosphate buffered saline saline and re-centrifuged.
Muram of mildipeptide bound to T-lympho-5 blasts are quantitated using the Morgan-Elson reaction (Example 1), resulting in 60-70 µg detected
muramyldipeptide 10 T-lymphoblasts. About
Example 7. By analogy with the described method, bovine serum albumin can be reacted with 2-acetamido-3-O-f0-1-1-l-1-carbamoyl-3-carboxy 15 propyl) -carbamoylethyl-carbamoylethyl -2-deoxy-0-glucose, 2-benzoylamino-3-O-b-1-L-1- (D-1-carbamoyl-3-carboxypropyl) -carbamoyl-methyl-carbamoylethyl-2-desoxy-alfa, be-20 ta-O-glucose, 2-benzoylamino-Z-O-l, -lr- (D-1-carbamoyl-Z-carboxypropyl) -carbamoylethyl-carbamoylmethyl - -2-deoxy-alpha, beta-D-glucose 2-acetamido -Z-O-f Ll- (Dl-Kap6a- 25 moylmethylcarbamoyl-3-carboxypropyl) -carbamoyl ethyl -carbamoylmethyl -2 -deoxy-O-glucose, 2-benzamido-2-deoxy-3-Of LI- (D-1-carbamoyl-3-carboxypropyl) -carbamoylpropyl - -carbamoylmethyl} -D-glucopyranose, 3-0-LI- (Dl - carbamoyl-3-carboxamide) -carbamoyl-cartil-carbamoylmethyl -2-deoxy-2-propionamido-b-glucose, 2-acetamido-3-0-fL-1- (D-1-carbamoyl-3-carboxypropyl) - 35 - carbamoylpropyl -carbamoylmethyl) -2-deoxy-O-glucose, 2-acetamine-3-0-1- (O-1-carbamoyl-3-carboxypropyl) -carbamoyl-2-hydroxyethyl-carbamoylmethyl -2-deoxy-0 - glucose, 40 2-propionylamino-3-0- {L-1- (D- 1,3-dicarboxypropyl) -carbamoylethyl) -carbamoylmethyl -2-deoxy-B-glucose, 2- Benzoylaminr-3-Og CL-1- (D-1- -N-carbamoylmethylcarbamoyl-3-carbo-45 xypropyl) -carbamoyl ethyl-carbamoylmethyl -2-deoxy-O-glucose, 2-acetamino-3-0- {LID- 1-carbamoyl-3-carboxypropyl) -carbamoyl-2-methylpropyl-carbamoylethyl} -2-deoxy-0- ate glucose 2-benzoylamino-3--10-ffb-1- - (D-1,3-dicarboxyprrpil) - Carbamoylethyl) -carbamoylmethyl -2 -2-deoox 1-2-acetamino-3--0-1 CD-1-fL-1-carbamoyl-3-carboxypropyl-; -carbamoyl-2 -methyl-propyl / -carbamryl-propyl -carbamoylethyl-j-carbamoylethyl Jr-2-deoxy-0-glonokozy, 2-aceta-60; mino-3-0-I-1 - {D-1,3-dicarboxypropyl-carbamoyl-2-methylpropyl - carbamoylmethyl -2-deoxy-0-glucose, 2-acetamino-3-O-1- (O-1-carbamoyl-3-carboxypropyl) -capramyl-N, N-tetra-J5
methylene -carbs1-methylmethyl -2-deoxy-D-glucose-2, 2-acetamine-3 0-tl - {D-1-carbamoyl-3-carboxypropyl) -carbamoylmethyl-N-methylcarbamoylmethyl -2-deoxy-O-glucose, 2 -benzoylamino-3-0-1, -1- (O-1-carbamoyl-3-carboxypropyl) -carbamoyl-2 methylpropyl -carbamoylmethyl-3-deoxy-B-glucose.
; Example 8  By the method analogous to that described in Example 3, sheep erythrocyte membranes are obtained, introduced into the coupling reaction with 2-acetamino-3-0-o-1-l-1- (0-1-carbamoyl 3-carboxypropyl) -carbamoylethyl-carbamoyl ethyl 2-deoxy-1) -glucose 2-benzoylamino-3-0-O-1-1-1- (D-1carbamoyl-3-carboxypropyl) -carbamoylethyl) -carbamoylethyl -2-deoxy-D-glucose, 2-benzoylamino -Z-0-f (b-1- (P-1-carbamoyl-3-carboxy-piperyl) -carbamoylethyl-carbamoylmethyl -2-deoxy-O-glucose, 2-benzoylamino-3-0-f LI- (D-1 , 3-dicarboxypropyl) -carbamoylethyl-carbamate-2-deoxy-P-glucose, 2-propionylamino-3-Of I L-1-OD-l-carbamoyl-3-carboxypropyl) -carbamoyl ethyl -carbamoylmethyl -2-deoxy-B-glucose, 2-acetamine-3-0- {L-1- (O-1-Y-carbamoylmethylcarbamoyl- 3-carboxypropyl) -carbamoylethyl -carbamoylmetlS-2-deoxy-0-glucose, 2-benzoylamkno-3-0-1-1- (Dl-carbamoyl-3-canboccypt) Opyl) -carbamoylpropyl-carbamoylmethyl, deoxy-glucose (.  2-Acetamino-3-0- (| Ll- (Dl-Carbamoyl-3-Carbortcipropyl) -carbamoylpropyl-Carbamoylmethyl5-2-disvksi-0-Gluk6oy, 2-acetamino-3-0-LI- (DI-carbamoyl-3 -carboxypropyl) -carbamoyl-2-hydroxyethyl1 -carbamoylmethyl j (-2-lezoxy-O-glucose, 2-propioiyl-amino-3-0-L-1- (B-1, Zdmicarboxygpropyl) -carbamoyl ethyl carbamoylmethyl -2-deoxy- P-glucose, 2-benzoylamino-3-0-G L-1- (E 1-N-carbamoylmethylcarbamoyl-3-carboxypropyl) carbamoyl ethyl-carbamoylmethyl -2-deoxy-O-glucose, 2-acetamino-3-O-. L-1- {Dl-carbamoyl-3-carboxypropyl) -carbamoyl-2-methylpropyl-carbomoylmethyl 5 -2-deoxy-O-glucose, 2-acetamine-3-0- | L-1-b-1- (0 -1-carbamoyl-3- / L-1 carboxyethyl / -carbamoylpropyl) -carbamoylethyl | -carbamoyl ethyl -2-deoxy-O-glucose, 2-acetamine-3-0-L-1- (, 3, -LIcarboxypropyl) -carbamoyl-2; -methylpropy; 17-carbamoylmethyl-2-deoxy-O-glucose , 2 Benzoylamino-3-0- {1 -1- (O-1-carbamoyl-3-carboxypropi) 1) g-carbamoyl-2-methylpropyl -carbamoylmethylJ-2-deoxy-O-glucose, 2-acetamine-3- 0- {ü-1- (O-1carbamoyl-3-carboxypropyl) -carbamoyl-N, N-tetra-1methylene-carbamoyl-methyl-2-deoxy and-D-glucose, 2-acetylamino-3-0-b-1- {0 -1-carbamoyl-3-carboxypropyl) -ka11bamoylethyl1 -Y-methylcarbamoylmethyl -2-deoxy-D-glucose, 2-acetamino 3-0-DI- {L-1-carba1Moyl-3-carboxypropyl) -carbamoyl-2-methyl Propyl -carbamoylethyl -2-deoxy-O-glucose.  Example 9  By analogy with the method described in Example 5, PEasraodium knowfesi malaria merioids are obtained, introduced into the reaction of combination with 2-acetamino-3-0- | 0-1-1- (0-1-carbamoyl-3-carboxy Xypropyl) -carbamoylethyl-carbamoyl ethyl -2-deoxy-B-glucose, 2-benzoylamine-3-O-CD-1-1-1- (0-1-carbamo-3-carboxypropyl) -carbamoylethyl-carbamoylethyl -2 -deoxy-0-glucose, 2-basoyl-amino-3-0-1-1: fV-1-carbamoyl-3-carboxypropyl) -carbamoyl ethyl-carbamoyl-methyl-2-deoxy-D-glucose, 2-benzoylamino-Z-O -G LI- (Dl, 3-dicarboxypropyl) -carbamoylethyl -carbamoylmethyl -2-deoxy-O-glucose, 2-prop Ionyl-but-3-0-b - 1- (0-1-carbamoyl-3-carboxypropyl) -carbamoylethyl-carbamoyl methyl -2-deoxy-O-glucose, 2-acetomino-3-Of L-1- (D-1-N-carbamylmethyl carbamoyl-3-carboxypropyl) -carbamoylmethyl | -carbamoylmethi7 2-deoxy-D-glucose, 2. -acetamino-3-0-LI- (D-1-N-carbamoylmethylcarbamoyl-3-carboxypropyl) -carbamoyl ethyl -carbamoylmethyl -2-deoxy-O-glucose, 2-bemozoylamino-3-0-b-1- {0- 1-carbamoyl-. 3-carboxypropyl) -carbamoylpropyl-carbamoylmethyl r2-dez, C-B-glucose, 2-acetylamino-3-O-.  - | | l-1- (0-1-carb amoyl-3-carboxypropyl) -carbamoylpropyl -carbamoylmethyl -2-deoxy-P-glucose, 2-acetamino-3-0- | L-1 - (O-1-carbamoyl-3-carboxypropyl) -carbamoyl-2-o1 {SistilD-car bamoylmethyl -2-des6xy-0-glucose 2-propionyl1-amino-3-0-1- (0-1 , 3-dicarboxypropyl) -carbamoyl ethyl -carbamoylmethyl -2-deoxy-0-glucose, 2-benzoylamino-3-0- (D-1-y-carbs-1moylmethylcarbamoyl-3-carboxypropyl) -carbamoyl ethyl-carbamoyl methyl -2 deoxy-0 -glucose, 2-acetomino-3-0-1- (O-1-carbamoyl-3. -carboxypropyl) -carbamoyl-2 -methyl propyl -Ar | bamoylmethyl -2-deoxy, -O-glucose, 2-ace. Tamino-3-O-D-1-.  - {Ь-1-1 a; -carbamoyl-3- (L 1-karbk {sietil) -carbamoylpropyl-carbamoylethyl | -carbamoylethyl -2-deoxy-0glucose, 2-aneTaM HO-3-0-j Ll- - (D-1, Z-dicarboxypropyl) -carbamoyl L-2 -methylpropyl -carbamoylmethyl-2-deoxy-O-glucose, 2 -benzoyl no-3-of LI- (D-β-carbamoyl-3-carb kcippbpj, n) -carbamoyl-2-methylpropyl carbamoylmethyl -2-deoxy-0-glucozoy, 2-acetamino-3-0- {l-1 - (0-1-carbamoyl-3-carboxypropyl) carba / mil-K, M-tetramethylene 3 -carba1-moylmethyl -2-deoxy-and-glucose, 2-acetamino-3-Of LI- (D-1-carbamoyl -Z-carboxypropyl) -carbamoylethyl -N-methylcarbamoylmethyl 2-deoxy-B-glu, goat, 2-acetamino-3-O-Dl-fL-1-carbamoyl-3-carboxypropyl) -carbamoyl-2-methylpropyl-ka bais yuil ethyl-2-deeoksi-and-glucose.  t J.  .   Example 10 In a solution of 100 mg of 2-acetamino-3-0- {o-1-L-l- (D-1-carbamoyl-t3-succinimidoxycarbonylpropyl) -carbamoyl ethide -. carbamoylethyl-2-deoxy-O-glucose in 10 ml of phosphate buffer physiological saline solution (pH 7.2) 10 dog breast cancers are suspended.  Suspension incubated for 90 min at room temperature.  The muramyl dipeptide addition product to the tumor cells is then sedimented by centrifugation and washed with phosphate buffered physiological saline-SALT solution by re-suspension of the product in it and re-centrifuging.  The quantitative determination of muramyl dipeptide associated with tumor cells was performed using the Morgan-Elson reaction (Example 1), as a result of which 6080 µg of muramyl dipeptide was detected per 10 breast cancer cells.  Example 11  By analogy according to the methods described in example 10, get cancer cells. the mammary gland, dogs connected to 2-acetamine-3-0- {o-1-1, -1- (D-1-carbamoyl-3-carboxypropyl) -carbamoyl ethyl -. CarbaMoylethyl -2-deoxy-P-glucose, 2-benzoyl # 1No-3-0 - {; 0-1-LL-1 - - {D-1-carbamoyl-3-carboxypropyl) -carbamoylethyl-carbamoylethyl -2-deoxy -D-glucose, 2-benzoylamino-3-0-l-1- (B-1-carbamoyl-3-carboxypropyl) -carbamoyl ethyl -carbamoylmethyl -2-deoxy-D-glucose, 2-benzoylamine-3-0-J C. (3-dikarboksipropil) -karbamoiletil -karbamoilmeTill-2-deoxy-D-glucose, 2-propionilamyno-3-O- {Ll- {D-1-carbamoyl-3-carboxypropyl) -kapbamoiletiJ carbamoylmethyl) -2-deoxy -1-glucose, 2-acetamino-3-0- {l-1- (0-1-M-carbamoylmethylcarbamoyl-3-carboxypropyl) -carbamoyl ethyl -carbamoylmethyl - 2-deoxy-B-glucose, 2-benzoylamino-3-0-1-1- (P-carbamoyl-3-carboxypropyl) -carbamoylpropyl-carbamoylmethyl -2-deoxy-O-glucose, 2-acetamine-3-0- L-1- (D-1-carbamoyl-3-carboxypropyl) -carbamoylpropyl-carbamoylmethyl-2-deoxy-D-glucose, 2-, acetamino. 3-0-Cy-1 (D-1-carbamoyl-3-carboxypropyl) -carbamoyl-2-hydroxyethyl} -carbamoylmethyl 3 2-deoxy-O-glucose, 2-propynylamino-3-0- | 1-1- ( O-1,3-dicarboxyprrpyl) -carbamoylethyl | -carbamoyl methyl1-2-deoxy-glucose, 2-benzoylamino-3-X) - 1 / -1- {O-1-Y-carbamo and methylcarbamoyl-3-carboxypropyl) Carbiyoyl ethyl-3-deoxy-O-glucoe, 2-acetamino-C 0-L-1- (D-1-carbamoyl-3-carboxypropyl-carbamoyl-2-methylpropyl-carbamoylmethyl -2-deoxy-D-glucoe.  2-acetamio-3O-D-1-L-1-D-1 -carbamoyl-3- (L-1-carboxystil Ucarbamoylpropyl-carbamoylethyl | -carbamoylethyl -2-deoxy-O-gga (gozo 2-acetamino-3- 0-LI- {DI, 3, -dicar boksiprbpil) -carbamoyl-2 -methylpropyl -carbamoylmethyl -2-deoxygl glucose, 2-benzoylamino-3-0-ir-l- - {D-1-carbamoyl-3-carboxypropyl ) -carbamoyl-2 -methylpropyl} -carbamoylmethyl -2-deoxy-1 -glucose, 2-acetamino-3-0- f L-1- {D-1-carbamoi-3-carboxypropyl) -carbamoyl-N, N tetramethylene - carbamoylmethyl5-2-deoxy-D-glucose, 2-acetamino-Z-O-f L-1- {D-1-carbamoyl-3-carboxypropyl) -carbamoyl ethyl} -N-methylcarbamoylmethyl-2-dezo Xi-O-glucose, 2-acetic acid "but-3-0-fo-1-L-l-carbamoyl-3-carboxypropyl) -carbamoyl-2-methylpropyl, -carbamoylethyl1-2-deoxy.  -D-glucose.  Example 12 .  100 mg of 2-acetamino-3-0 - {{1. Are added to 10 ml of vaccine suspensions in a culture of ktsura (Vakzine Beringwerke) in phosphate buffered saline. -1- (O-1-carbamoyl-3-succin10L ideoisocarbonylpropyl) -carbamoylethy-carbamoylmethyl -2-deoxy-O-glucose (Suspension shake for 4 h at 4c.  After this, the product is fed to the virus under sterile conditions at the presence of the dinene mura dalipeptide, by means of dyLysis against water, separation from the low molecular weight reaction products is carried out, after which the sublimation drying is carried out.  Quantitative determination of Muramyl. the dipeptide associated with the virus and is produced using the Morgan-Elson reaction (Example 1), Example 13.  By analogy with the method described in Example 12, the schur vaccine linked to 2-acetamino-3-0-O-1- | b-1- (O-1-car bamoyl-3-carboxypropyl) -carbamoyl ethyl T-carbamoylethyl -, 2-desrksi-O-glucose, 2-benzoyl-11-3-0-O 1-tl - -1- {D-G-carbamoyl-3-carboxypropyl) -carba yuylethyl} -carbamoylethyl -2-deoxy-B - glucose, 2-benzonla "nnogZ-0-f L- -j Dl-carbglmoyl-3-carbox-propyll j-to arbamoylethyl-D-arbamoylmethyl-2-deoxy / -B-glucose, 2-beneo: iHa1 -1-deoxy / -B-glucose, 2-beneo: -Ha-1-deoxy-2-deoxy / -B-glucose, 2-beno-arbamoyl ethyl -2-deoxy / -B-glucose, 2-beno: - L-1- (0-1,3-dicarboxyprobyl) -carbamoyl-methyl-carbamoyl-methyl-2-deoxy-B-g, lukozy, 2-propionyl aMHHo-3-0- {fL-l- (D-1-carbamoyl -3-carbox propyl) -carbamoyl ethyl-3-carbamog, ita-1-methyl-2-deoxy-O-lukozy, 2-acetamino-3-0- {1 | -1- {DlN-carbamoylmethylcarbamoyl-3-carboxypro-PIL) -carbamoyl methyl-carbamoylmethyl) 2-deoxy-glucose, 2-benzoylamino-Z-6-e LI- {D-1-carbamoyl-Z-carboxypropyl) -carbamoyl-2-deoxy-O-glucose, 2-acetylin-3-0- . {H, -1 (DI-carbamoyl-3-carboxypropyl) -carbamoylpropyl -carbamoylmethyl-T-2-dehydroxy-D-glucose, 2-aceta-1Ushnr-3-0-, f LI- (D-1-car 6amoyl-3-carbox1-propane carbamosh1-2-hydroxyethyl7-yarbamosh2-2 deoxy-O-glucose, 2-propionyl 1tno-3-of LI- (D-1,3-lncarboxypropyl) -carbamoyl-methyl-carbamoylmethyl -2-deoxy-O-glucose, 2- benzoylamino-3-0-fL-1- (0-1-I-carb amoylmethylcarbamoyl-3-carboxypropyl) -carba. Myethyl-Carbamoylmethyl -2-deoxy-O-glucum & 2-acetamind-3-0-5 {L-1- - (O-1-car-6amoyl-3-carboxy-proyl) carbamoyl-2-methylpropyl-carbamoylmethyl -2- deoxy-b-glucose, 2-acetamino-3-0-Dl-fL-l-fb-1-carbamoyl-3- (L-1-carboxyethyl) -carbamoylpropyl-2-carvam1-methylstil-carbamoyl-methyl-2-deoxy. -B-glucose, 2-acetamino-3-0-fL-1- (D-1,3-dicarboxypropyl) -carbamoyl-2-methylpropylJ-to arbamoylmethyl 2-deoxy-B-glucose, 2-benzoylamino-3-0 - l-1- (Dl-carb moyl-Zcarboxypropyl) -carbamoyl-2-methylpropyl carbamoylmethyl -2-deoxy-I-D-glucose, 2-acetamino-3-0-b- 1- (O-1-carbg1moyl-3 -carboxypropyl) carbamoyl-N, S - etramethylene1-carbamoylmethyl -2-deoxy and O-glucose, 2-acetamino-3-0-1- {B-1-carbamone-3-carboxypropyl) -carbamoylstilz --Y-methylcarbe No. Omethyl -2-dvsoxy-D-glucose, 2-acetamino-3-O-fD-1-1-1-carbamoyl-3-carboxyl-propyl-kbamoyl-2-methylpropyl | -car - bamoilzti LZ -2-deoxy-1) -glucose.  Example 14  By analogy with the method described in Example B, CBA / mussel T-lymphoblasts linked to 2-acetamino-3-0-D-1- - (B-1- (O-1-kgframoyl-3-carboxyep1p3)) are obtained -carbamoyl ethyl -carbamoyloxy 2-deoxy-B-glucose, 2-benzoylamino-3-0- (E) -1- | 1, -1- {0-1-carbamoyl-3-carboxyp ropyl) -carbamoylztil-carbamonylethyl -2 -deoxy-o-glucose, 2-benzoylamino-3-0-LI- (D l-carbamoyl-3-carboxypropyl) g to arbamoyl and l these l-carbamoylmethyl -2-deoxy-C-gluco-ZOY, 2- benzoylaminr-3-0- {L-1- {D-1, 3-dicarboxypropyl) -carbamoyl ethyl car. baiylmethyl 2-des. oxy-P-glux-zoy, 2-propionamino-3-0-L-1- (P-1-carbamoyl-3-carbsS-xypropyl) -carbambyllethyd3-carbamoylmethyl | -2-deoxyglucoe, 2-acvtamino-3-0- {1 . -1- (B-1-K carbamoylmethylcarbamoyl 3-carboxypropyl) -carbamoylztil-carbamoylmethyl -2-deoxy-0-glucose, 2-benzo. ilapino-3-0-l-{D-l-carbamate-3-carboximpropyl) -carbamoylpropyl-carbamoylmethyl -2-deoxy. -O-glucoeoy, 2-acetylamino-3-0-j L-l- (D-l--carbamoyl-3-carboxypropyl) -carbamoylpropyl | -carbamoylmethyl -2-desox C-B-glucose, 2-acetamino-3-O- f. L; -1- (D-1-carbamoyl-3-carboxypropyl) -carbamoyl-2-hydroxyethyl-carbamoylmethyl-J-2-deoxy-D-glucocoic,.  2-propiomylamino-3-0- ((O-1, 3-dicarboxypropyl) -carbamoylethyl-carbamoylmethyl -2-deoxy-G-glucose, 2-benzoylamino-3-0-1-1- (P-1-Ycarbamoylmethyl. carbamoyl-3-carboxypropyl) -carbamoyl and 1ethyl) -carbamoylmethyl-2-deoxy-B-glucose, 2-acetomino-3-O-C Li-1D-1-carbamoyl-3-carboxypropyl) -carbamoyl-2-methyl propyl -carbamoylmethyl -2-deoxy-P-glucose, 2-acetamino-3-0-o-1-L-1-P-1-carbamoyl-3- (L-1-carboxy ethyl) -carbamoylpropyl-carbamoylethyl-carbamoylethyl - 2-deoxy-1) -glucose, 2-acetamino-3-0- {L-1- (D-1,3-dicarb6-hydroxypropyl) -carbamoyl -2-methylpropyl-carbamoylmethyl} -2-deoxy-C-glucose, 2 -benzoylamino-3-0-f Ll- (Dl-carbamate-3-carbox propyl) -carbamoyl-2 -methylpropyl} -carbamoylmethyl} -2-deoxy-and-glucozu. , 2-acetamino-3-O-LI- (DI-carb amoyl-3-carboxypropyl) -carbamoyl-N, N-tetramethylene 3 -carbamoylmethyl -2-deoxy-1) -glucose, 2-acetamino-3-O-L -1- (D-1-carbamoyl-3-carboxypropyl) -carbamoylethylT-K-methylcarbamoylmethyl} -2-deoxy-1) -glucose, 2-acetamino-3-0-o-1 - {L-1-carbamoyl -3-carboxypropyl) -carbamoyl-2 -methylpropyl -carbamoylethyl -2-deoxy-B-glucose.  Example 15  1 mg of the product of the interaction of albumin & amphibian serum and 2-aueTaMHHo-3-0-f LI (D-1-carbamoyl-3-carboxypropyl) -carbamoylethyl-j-carbamoylmethyl} -2-deoxy-TZ-gluiosis is dissolved in 0.1 MP of phosphate buffered saline saline (PBS).  To the prepared solution, 0.1 ml of a 5% suspension of carboxymethylcellulose in PBS was added.  The mixture of tw-mind in equal portions is intramuscularly administered in guinea pigs.  Example 16.  The product of the interaction between 10P T-lymphoblasts and 2-ai, e amino-3-0-1-1- (0-carbamoyl-3-carboxypropyl) -carbamoyl ethyl-D-carbamoylmethyl - 2-deoxy-B-glucose (Example 6) is suspended in 0.5 ml of phosphate buffered saline saline (PBS).  0.5 ml of a 5% suspension of carboxymethylcellulose in PBS is added to the added suspension.  0.1 MP of the mixture is subcutaneously injected into each mouse.  Example 17: To a 10 ml suspension of HPS vaccine against rabies (Behring-werke) in a phosphate buffer physiological saline solution, add 100 mg (0.017 mmol) of 2-acetamino-3-0-b-1- (0-1 -carbamoyl-3-succinimidooxycarbonylpropyl) -carbamoyl ethyl -carbamoylmethyl -2-deoxy-B-glucose.  The concentration of the virus is 210 OO / min in 1 ml of suspension.  The slurry is shaken for 4 hours at 4c.  After that, the product of the interaction of HDV vaccine against rabies and the muramildipeptide is filtered under sterile conditions, by dialysis with water, the separation from the low molecular weight reaction products is carried out and then freeze-drying is carried out.  Example 18  By analogy with the method described in example 17, a nasal rabies vaccine (Behringwerke) is obtained, linked to 2-acetamino-3-0- (P-1-carbamoyl-3-carboxypropyl) -carbamoylethyl-carbamoylethyl -2-deoxy -0-glucose, 2-benzoylamino-3-0- | O-1-b-1- (D-1-carbamoyl-З-к. arboxypropyl) -carbamoylztil-carbamoyl ethetet 2-deoxy-J-glucose, 2-benzo-lamino-3-0- {P-1- (D-1-carbamoyl-3-carboxypropyl) -carbamoylztil-carbimemomethyl 2-desoxy-B-glucose , 2-benzoylamin6-3-0- {l-1- (B-1,3-dicarboxylpropyl) -carbamoylethylJ-arabamoylmethyl -2-deoxy-1) -glycose, 2-propionylamino-3-0- {h-1- (P-1-carbamoyl-3-carboxypropyl) -carbamoylztil - - -carbamoylmethyl -2-deoxy-B-glucose, 2-acetamino-3-0- {L-1- (D-1-Ncarbamoylmethylcarbamoyl-3-carboxypropyl) - carbamoyl ethyl D-carbamoylmethyl -2-deoxy-C-glucose, 2-benzoylamino-3-0-1, -1- (O-1-carbamoyl-3-carboxypropyl ) -carbamoylpropyl}: -carbamoylmethyl5-2-deoxy-V-glucose-2-acetylamino-3-0- {h-1- {L-l-carbamoyl-3-carbox-propyl) -carbamylOi-ilppi-carbamoyl hydrochloromethyl-3-carbamocipropyl) -carbamoyl-3-carboxymethyl -glucose, 2-acetamino-3-0-L-1- (D-1-carbamoyl-3-carboxypropyl) -carbamoyl-2-hydroxyethyl | -carbamoylmethyl-2-deoxy-0-glucose, 2-propionylamino-3-0- {C-1- (O-1,3-dicarboxypropyl) -carbamoyl ethyl-carbamoylmethyl} -2-deoxy-B-glucoEy, 2-benzoylamino -3-0-1- (O-1-N-carbamoylmethyl-carbamoyl-3-carboxypropyl) -carbamoylethyl-3-carbamoylmethyl -2-deoxy-D-glucose, 2-acetamine-3-0-f Ll- (Dl -carbamoyl-3-carbox propyl) -carbamoyl-2 -methylproj3 -carbamoylmethyl -2-deoxy-B-glucose, 2-acetamino-3-O-P-1- (-car6amoyl-3- (b-1-carboxy9til) -carbamoylpropylT-carbamoyl etnte-carbamoyl ethyl -2-deoxy-1) -glycoso 2-acetamino-3-0- (h-1- {0-1,3-dicarboxypropyl) -carbamyyl-2-methyl opit-β-carbamoylmethyl -2-deoxid-B-glucose, 2-benzosch1amino-3-0- (L-1 i- (O-1-carbamoyl-3-carboxypropyl1 Gcarbamo l-2 -methylpropylZ, -carbamoyl methyl -2-deoxy -B-glucosay, 2-acetyamio-3-0- {l-1- (B-1-carbamoyl-3tcarboksip opil) -carbamoyl-N, N-tetramethyl-carbamoylmethyl-2-deoxy-B-glucose, 2- acetamino-3-O- | b-1- (D-1-carbamoyl-3-carboxypropyl) - to arb ambil et l -N-meth and l car bamoi lme til-2-deoxy-p-glucose, 2 -acetamino-3-O-tD-1 (L-1-carbamoyl-3-g -carboxypropyl-carbamoyl-2-methylpropyl-3 -carbamoylethyl -2-deoxy-B-glucose.  Example 19  100 mg (0.17 mmol) of 2-acetamino-3-0- {Ll- (Dl "can-6-amio-3- CycminimidooxicapboneHylpol il) -capbamoylethyl2 -carba1moylmethyl3 -2-deoxy IgG-glucose, virus Anfigen t get way (Behringwerke) in a similar way to obtain 41 Begrlva ES Concert composition composition E.  in 1 ml of suspension.  The suspension is shaken for 4 hours at 4 ° C.  After that, the product of the interaction of virus antigen and muramyl dipeptide by means of dialysis with phosphate buffered physiological saline solution is separated from low molecular weight products in the reaction, the dialyzed suspension is frozen and stored at 20 ° C before use.  EXAMPLE 20 By analogy with the method described in Example 19, an influenza virus antigen is obtained, its activity is nanyi 2-acetamino-3-0- | 0-1-Gy-1- (0-1-carbamoyl 3-carboxypropyl) -carbamoylethyl-carbamoyl ethyl -2-dezok-ca-D-glucose, 2-benzoylamino-3-0si-D-glucose, 2-benz - Dl-tL-l-fo-lK arbamoyl-3-k arbox propyl ) carbamoylethyl} -carbamoylethyl3 -2-des6xy-C glucose, 2-benoyloyl but-3g 0-h-1-r (D-1-carbamoyl-3-car6o sipropil) -carbamoyl ethyl 3 -carbamoyl methylZ-2-deoxy-0- glucose, 2-bin. Eoyl1-iino-3-0-li-i- (Dl, Z-dicarbok cypropyl) -carbamoyl etnlS-carbamoyl methi / y-2-deoxy-o-glucose, 2-proHHoHHJtaMHHO-3-0-j tL-l- (О- 1-carbamo-3-carboxypropyl) -carbamoyl ethe T-carbamoylmethyl -2-deoxy-O-glucose, 2-acetamino-3-0-1, -1 (D-1-K-to ambol omelet or arb amoyl- 3 - carboxn propyl) -carbamoyl ethyl 3-carbamoylmethyl 3 -2-deoxy-0-gl1b oeoy, 2-benzoylamino-3-0- (C-1- (0-1-carbamoyl 3-koxypropyl) -carbamoyl propyl 3-carbamoylmethyl 3-deoxy -O-glucose, 2-acetylamino-3-0- (L-1- (0-1-carbamoyl-3-carboxypropn) -carbamoylpropyl 3 -carbamoylmethyl} -2-deoxy-O-glucose, 2-acetates but-3-0-. L-1- (o-1-carbamoyl-3-carboxypr011 "l) -carbamoyl-2-hydroxyethyl-3-carbamoylmethyl1-2-deoxy-O-glucose, 2-propionylamino-3-0-G111-1- (O-1 , 3-dicarboxy propyl) -karbamoileti -karbamoilmatil -2-deoxy-O-glucose, 2-benzoylamino-3-0-t {LI- (D-lSN-karbamrilmetilkarbamoil-3-carboxypropyl) -karbamoiletilZ -karbamoilmetilZ-2-deoxy -O-glucose, 2-acetg1myno-3-0- (L-1-O-1-carbamoyl-3-carboxypropyl) -carbamoyl-2-methylpropyl 3-carbamoylmevil -2-deoxy-0-glucose 2-acetamino-3- 0 -O-1- {L-1-o-1-carba 1oyl-3- {L-1-carboxy (tely) -car1bamoylpropyl | -carbamoylethylj-carba milylethyl -2-deoxy-1 -glucose g 2-acetamino-3-0- | L-1- (D-1, 3-dicarboxypropyl) -carbamoyl-2-methylpropyl-k-rbamrylmethyl} -2-deoxy-D-glucose, 2-benzoylamino-3-0-ЬЬ 1 (o-1-carbamoyl-3 -carboxypropyl) -carbamoyl-2-methylpropyl 3-carvamoylmethyl-5-2-deoxy-O-glucose, 2-acetale-1-HNO-3-0- {| b-1- (O-1-carbamoyl-3-carboxypropyl) -carbamoyl-N, N-tetramethyl 3-carbamoylmethyl 3-2-deoxy-OyGlucose, 2-acet1 Mino-3-0- | b-1- (0-1-carbamoyl-3-carboxy-propyl) -carbamoyl ethyl 3 -N-methylcarbam moylmethyl-2-deoxy -1-glucose, 2: β-acetaminy-3-0- {o-1- (L-1-carbamoyl-1-3-carboxypropyl) -carbamoyl-2 -me | tylpropyl 3 -carbamoylethyl-2-deza) xi-3) g lucosis.  PRI and MER 21.  To 2 ml of a solution of columnar serum in phos; fatal buffer saline salt is added.  10 mg 2-acet. amido-3-0-l-1- (O-1-carbamoyl-3-succinimidooxycarbonylpropyl) -carbamoylethyl3 -carbamoylmethyl -2-deoxan-B-glucose.  The concentration of columnar serum is 3 mg / ml.  The solution is stirred for 4 hours at 4 ° C. After that, the product of the interaction of columnar serum with muramyl dipeptide is separated by ultrafiltration from low molecular weight Culinary reaction products.  The filtered solution is frozen and stored until use at -20 ° C.  A quantitative distribution (by the Morgan-Elson reaction) indicates the presence of approximately 50 µg of muramyl dipeptide per 1 mg of the product of the interaction of stubborn serum and muramyl dipeptide.  Example 22 By analogy with the method described in Example 21, anti-columnar serum bound to 2-ace amino-3-0-0-1-1 is obtained. -1- {0-1-carbamoyl-3-carboxypro; drank) -car6amoylethylT-carbamoylethyl} -2-deoxy-D-glucose, 2-benorlamino-3-0-D 1 -l-l- (Dl-karba lQIL-3-carboxypropyl-carbamoylethyl | -car 5a milethyl -2- deoxy-1) -glucose, 2 benzoylamino-3-0- {L-1-. {C-1-carbamoyl-3-carboxypropyl) -carbamoylethyJ-carbamoylmethyl -2-deoxy-1) -glucoZo, 2-benzoylamino-3-0-LI- (D-1, 3 dicarboxypropyl) -carbamoyl ethyl-carbamoylmethyl -2- deoxy-B-glucose, 2-propionylamino-3-0-L-1- (D-1 -carbamoyl 3-carboxyprop. il) -carbamoylethyl} -carbamoylmethyl5-2-deoxy-D-glucose, 2-acetamino-3-0- | l-1- (D-1-carbamoylmethyl-carbamoyl-3-carg boksipropil) -carbamoyl ethyl -carbamoylmethyl -2-deoxy-1); - glucose, 2-benoylamino-3-0-1-1- (P-1-carbamoyl- 3-carboxypropyl) -carbamoylpropyl -carbamoylmethyl -2-deoxy-1-glucose, 2-acetyllamino-3-0- {| L-r1I- (D-1-carbamoyl-3-carboxypropyl) -carbamoylpropyl 3-carbamoylmethyl -2 | -deoxy-C-glucose, 2-acetamino-3-0- | l-1- (B-1-carbamoyl-3-carboxypropyl) -carbamoyl-2-hydroxyethyl-D-carbamoylmethyl -2-deoxy-B-glucose, 2-propyoylamino-3-0-LI- (DI, 3t-dicarboxypropyl) - carbamoyl ethyl carbamoylmethyl -2-deoxy-1) -glcose, 2-benzoylamino-3-0- {L-1- (D-1-Y-carbamoylmethylcarbamoyl-3 3-car boxypropyl) -carbamoyl ethyl carbamoylmethyl -2-deoxy- 1) -glucose, (2-acetamino-3-0- {l-1- (0-1-carbamoyl-3-carboxypropyl) -carbamoyl-2-methylpropyl-carbamoylmethyl-2-deoxy B-glucose, 2-acetamine- Z-O-D-1- {LI-D-1-carbamoyl-3- {L-1-carboxy ethyl) -carbamoylpropyl -carbamoyl ethyl -carbamsyl ethyl -2-deoxy-1) -glu Oz, 2-acetamino-3-0-L-1- (D. -1/3, dicarboxypropyl) -carbamOyl-2 -methyl propyl -carbamoylmethyl -2-deoxy-J-glucose, 2-benzoylamino-3-0-LI- (D-1-carbamoyl-3-carboxypropyl) -carbamoyl-2 -methylpropyl | -carba moylmethyl -2-deoxy-B-glucose, 2-acetamino-3-0-Ll- (I l carbamoyl-3-carbox oxipropyl) -carbamoyl-S, I-tetramethylene -carbamoylmethyl -2-deoxy-P-glucose, 2-acetamino-3-O (l-1- {O-1-carbamoyl-3-carboxypropyl) -carbamoylethyl 1} -N-methylcarbamoyl methylZ-2-deoxy-B-glucose, 2-acetamino-3-0- { CD- - {Ll-carbamate-3-carboxamide) -carbamoyl-2-methylpropyl-carbamate -2-deoxy-B-glucose, Example 23.  A qyum of an anti-cholera serum solution From the Vibrlochoraee in phosphate buffered physiological saline solution, 50 "mg of 2-acetamido-3-Og (0-1-carbamoyl-3-succinimI-hydroxycarbonylpropyl) -carbamoyl ethyl-carbamoylmethyl-2-2-2-a-hydroxycarbonylpropyl) -carbamoyl ethyl-carbamoylmethyl-2-2-2-carbamoyl-3-carbamoylcarbonyl-3-carbamoylthiol-2-acetamido-carbamoyl-3-og-carbamoylcarbamoylthiol-5-carbamoylcarbamoyl-3-carbamoyl-2-acetamido-3-Ogcarbamoyl-3-carbamide-5-carbamoyl-3-carbamoyl-3-carbamoylthiol-2-acetamido-3-Ogcarbamoylthiol-2-acetamido-3-Og. .  The protein concentration in the solution is 0.6 mg / ml.  The solution is stirred for 4 hours at 4c.  Thereafter, the product of the interaction of anti-cholera serum with muramyl dipeptide is separated by means of an ultrafilter.  NIN from low molecular weight reaction products.  The filtered solution is frozen and stored until use at -20 ° C.  Quantitative determination (by the Morgan-Elson reaction) shows the presence of 40-50 µg of muramyl dipeptide per 1 mg of the product of the interaction of antichol serum with muramyl dipeptide, Example 24.  By analogy with the method described in Example 23, columnar serum coupled with 2-acetamino-Z-O-DI-LI- (D-1-carbamoyl-3-carboxypropyl) -carbamoylethyl-carbamoylethyl-2-deoxy-TZ is obtained - glucose, 2-benzoyllamino-3-0-o-1-l-1- (0-1-carbamoyl-3-carboxypropyl) -carbamoylethyl-carbamoylethyl -2-deoxy-p-glucose, 2-benzoylamino-3-0 - C1-1- (L-1-carba-.  Moyl-3-carboxypropyl) -carbamoylethyl. ) -carbamoylmethyl-2-deoxy-T) -glucose 4 2-benzoyllamino-3-0-Cb-1- (D-i, 3-.  dicarboxypropyl) -carbamoyl ethyl -carbamoylmethyl-2-desoxy-D-glucose, 2-propionylamino-3-0-L-1- (0-1-carbamoyl-3-carboxypg) opil) -caramoyl ethyl-carbamo-amo B-glucose, 2-acetamino-3m O-L-1- (O-1-s-carbamoylmethylcarbamoyl-3-carboxypropyl) -carbamoyl ethyl -carbamoylmethyl} - 2-deoxy-TZ-glucose, 2-benzoylamino-Z-O- {l-1- (O-1-carbamoyl-3-carboxypropyl) -carbamoylpropyl -carbamoylmethyl -2-deoxy-1) -glucose, 2-acetylamino-3-0-L-1- (P-1-carbaMoyl-3 -carboxypropyl) -carbamoylpropyl -carbamoylmethyl -2-deoxy-0-glucose, 2-acetaMyb-3-0- {jj-l- (Dl-, -carbamoyl 3-carboxypropyl) -carbamoyl-2-hydroxyethyl-carbamoylmethyl -2-deoxy-B-glucose, 2-propionylsgmino-3-0- {i-1- (0-1, 3-dicarboxypropyl) -carbamoyl ethyl -carbamoylmethyl-2- eoxy-P-glucose, 2-benzoylamino-3-0-L-1- (0-1-N-carbamoylmethylcarbamoyl-3-carboxypropyl) -carbamoylethyl-Carbamoylmethyl -2-deoxy-T-glucose, 2-acetamino-3- 0-Cb-1- (Dl-carbamoyl-3-carbocipropyl) -carbamoyl-2-methylpropyl-carbamoylmethyl-2-deoxy-b-glucose, 2-acetamino-3-O-fD-1-1-1-carbamoyl -3- (D-1-carboxyethyl) -carbamoylpropyl 3 -carbamoyl ethyl-carbamoylethyl -2-deoxy-B-glucoea, 2-acetamino - 3-0- {L-1-o (1,3, -dicarbok ipropyl) -carbamryl-2 -methylpropyl -carbamoylmethyl -2-deoxy-J-glucose, 2-6eneoyl-amino-3-0- ((0-1-carbamryl-3-carboxypropyl) -carbamoyl-2 -methylpropyl -carbamoyl methyl -2-deoxy-B-glucoey, 2-acetamino-3-0- | b-1. - (O-1-carbamoyl-3-carboxypropyl) -carbamoyl-N, N-tetramethylene-carbamoylmethyl -2-deoxy-rD-glucose, 2-acetamino-3-O-f L-1 - - (D-1- carbamoyl-3-carboxypropyl) -carbamoyl ethyl -N-methylcarbamoylmethyl -2-deoxy-P-glucose, 2-acetamino-3-0-o-1- (L-1-carbamoyl-3-carboxypropyl) -carbamoyl-2-methylpropyl -carbamoylethyl -2-deoxy-T) -glucose.  Example 25  20mg of synthetic eicosapeptide, which is identical to the C-terminal sequence of human choriogonadotropin (HCG), and 30 mg of 2-acetamido-3-0- {l-1- (O-1-carbamoyl-3-succinimidooxycarbonyl propyl) -carbamoyl ethyl-carbamoylmethyl -2 -deoxy-1) -glucose is dissolved in 2 ml of sodium phosphate buffer solution (pH 7.2).  The solution is stirred at room temperature for 6 hours. After that, the product of the interaction of the eicosapeptide with muramyl dipeptide is isolated by chromatography on a column (1.4 x 40 cm) filled with Sephadex G-25 using water as an eluent and its eluate is freeze-dried.  A quantitative amino acid analysis shows that one molecule-j, lamuramyl dipeptide is attached to one molecule of eicosapeptide.  Example 26  By analogy with the method described in Example 25, a human C-terminal ecosapeptide fragment of human chorionogonadotropin is obtained, which is bound to 2-acetamino-3-O- {p-1-Ll- (Dl-carbamoyl-3-carboximide-3) -carbamoyl ethyl 3 -carbeyloyl ethyl -2-deoxy-1) -glucose, 2-benzoylamino-3-0- {o-1-y-1- (o-1-carbamoyl-3-carboxypropyl) -carbamoylethyl | -carbamoylethyl-2-deoxy-T -glucose 2-benzoylamino-3-0-1, -1- (D-1-carbamoyl-3-carboxypropyl) -carbamoyl ethyl -carbamoylmethyl -2-desokoi-B-glucose, 2-benzoylamino-3-0- 1, - 1- - (Dl, 3-dikarboboksipropil) -carbamoylethyl) -carbamoylmethyl -2-deoxy-1 (-glucose, 2-pro pionylamines-3-O-fL-1- (D-1-carbamoyl-3-carboxypropyl) -carbamoylethyl3 -carbamoylmethyl) -2-deoxy-O-glucose, 2-acetamine O-.  -3-0-G1-1- (D-1-N-carbamoyl yutylcarbemoyl-3-carboxypropyl) -carbamoyl ethyl-D carbamoylmethyl -2-deoxy-1) -Gluco30Y, 2-benzoylamino-3-0- {i-1 - (D-1-carbamoyl-3-carboxypropyl) -carbamoylpropane-J-carbamoylmethyl -2-deoxy-B-glucose, 2-acetylminoHo-3-0-l. Ll- {D-1-carbamoyl-3-carboxypropyl} -carbamoylpropyl 3 -carbamoylmethyl -2-deoxy-B-glucose, 2-aietamino-3-0- {(Dl-carbamoyl-3-carboxy-propyl) -carbamoyl-2-hydroxy-hydroxy-propyl) -carbamoyl-2-hydroxy-3-carboxypropyl-3-carboxypropyl-2-aietamino-2-hydroxypropyl-3-carboxypropyl} -carbamoylmethyl -2-deoxy-B-glucose, 2-propionylamino-3 O-L-1- (D-1,3-dicarboxypropyl) -carbamoyl ethyl -carbamoylmethyl -2-deoxy-TZ-glucose, 2-benzoylamino-3- O-L-1- (p-1-N-carbamoylmethylcarbamoyl-3-carboxypropyl) -carbamoyl ethyl-3 -carbamoylmethyl-3-deoxy-1) -glucose, 2-acetamino-3-0- (| L-1- (D- 1-carbamoyl-3-carboxypropyl) -carbamoyl-2-methylpropyl-carbamoylmethyl -2-deoxy-B-glucose, 2-acetamino-3-O- o- 1-b-1-o-1-carbamoyl-3- (b-1-carboxyethyl) -carbamoylpropyl -carbgiloylethyl-carbamoylethyl -2-deoxy-0-glucose, 2-acetamino-3-0-f L-1- ( D-1,3-dicarboxypropyl) -carbamoyl-2-methylpropyl -carbamoylmethyl -2-deoxy-1) -glucose, 2-benzoylamino-3-0- (; ь-1- (O-1-carbamoyl-3-carboxypropyl ) -carbamoi. n-2 -methylpropyl -carbamoylmethyl} -2-.  -deoxy-B-gluCozoic, 2-acetamino-3-0-1- (O-1-carbamoyl-3-carboxypropyl) -carbamoyl-M, N-tetramethylene 1 -carbamoylmethyl -2-deoxy-T) -glucose, 2-acetamino-3-0- {L-1- (D-1-carbamoyl-3-carboxypropyl) -carbamoylethyl-N-methylcarbamoylmethyl-2-deoxy-B-glucose, 2-acetamino-3-O-fD-1 - (Ll-carbamate-3-carboxamide) -carbamoyl-2 -methylpropyl -carbamoyl ethyl -2-deoxy-T) -glucose.   Example 27  By analogy with the method described in Example 1, bovine serum albumin is obtained, which is bound to 2-acetamino-3-0 - {(o-1-β-carbamoyl-3-carboxypropyl) mobilmethyl-N-methylcarbamoylmethyl 3--2- des-B-glucose, 2-benzoylamino-3-0- (D-1-carbamoyl-3-carboxypropyl) -carbamoylmethyl-N-methylcarbamoylmethyl-2-deoxy-T) -glucose, 2-acetamino-3-0- | {L-1- (0-1-carbamoyl-3-car-hydroxypropyl) -carbamoyl-3-carboxypropyl-carbamoylethyl-E-ethylcarbamoyl ethyl 3-deoxy-B-glucose, 2-acetamino-3-0- {b; - 1- (O-1-carbamoyl-3-carboxypropyl) -carbamoylpropyl -Y-methylcarbamoylmethyl-3-2-deoxy-D-glucose, 2-acetamium-3-0-t-l- (D-1-carbamoyl-3-carboxypropyl ) -carbamoylpropyl -N-ethylcarbamoylmethyl -2-deoxy-B-glucose, 2-benzamido-3-Of f L-1- (O-1-carbamoyl-3-carboxypropnl) -carbamoylpropyl -Y-ethylcarbamoylmethyl -2-deoxy- B-glucose, 2-acetamino-3-0- {b-1-- (D-1-carbamoyl-3-carboxypropyl). -carbamoyl ethyl -N-propylcarbamoylmethyl -2-deoxy-B-glucose, 2-acetamino-3-0-Ll- (Dl-carbamoyl-3-carboxypropyl) -carbamoyl-N, N-pentaM 9Tylene-carbamoylmethyl-2-deoxy- In glucose, 2-benoylamino-3-O-L-1-g (1 -1-carbamoyl-3-carboxypropyl) -carbamoyl-S, N-pentamethylene-; -carbamoylmethyl -2-deoxy-D-glucose, 2-acetamino-3-0-CL-1- (D-1-carbamoyl-3-carboxypropyl) -N-methylcarbamoyl ethyl-2-carbamoylmethyl-2-deoxy-O-glucose, 2 acetamino -3-0- | D-l- {0-1-carbamoyl-3-carboxypropyl) -carbamoylmethyl -N-methylcar bamoylethyl1-2-deoxy-T) -glucose,.  2-benzoylamino-3-0-o-1- (D-1-carbamoyl-3-carbox. cypropyl) -carbamoylmethyl1-M-methylcarbamoylethyl; -2-deoxy-D-rJjroK03Oft, 2-acetamino-3-0- {O-1-, (B-1-carby oil-3-carboxypropyl -carbamoyl ethyl 3 -M-ethylcarbamoylethyl} -2 deoxy-P-glucose, 2 -acetamino-ss-o-go. -1-G1-1- (0-1-carbam yl-3-carboxypropyl -carbamoylpropyl -M-methylcarbamoylethyl -2-deoxy-D-glucose, 2-acetamino-3-0-b-1-L-1- ( O-1-carbamoyl-3-carboxy #: ipropyl) -carbamoylpropyl -N-ethylcarbamoylmethyl -2-deoxy-D-glucose, 2-benzamido-3-O-DI-L- (0-1-carbamoyl-3 -carboxypropyl) -carbamoylpropyl} -N-ethylcarbamoylethyl -2-deoxy-B-glucose, 2-acet-amino-3-0-O-1-1-1- (O-1-carbamoyl-3-carboxypropyl) -carbamoyl ethyl -H-propylcarbamoyl ethyl -2-deoxy-P-glucose, 2-acetamino-3-0-pp1-1- (O-1-carbamoyl-3-carboxypropyl) -carbamoyl-S K-pentamethylene-carbamoyl ethyl-2- deoxy-0-glucose d, 2-benzoylamino-3-0-O-1-1-1 (O-1-carbamoyl-3-carboxypro; Peel) -carbamoyl-S, N-pentamethylene-, -carbamoylethyl-2-deoxy-B-glucose , 2-acetamino-3-0-DI-LI- (DI-carbamoyl-3-carboxypropyl) -N-methylcarbamoylethyl-carbamoylethyl-3-deoxy-D-glucose, 2-acetamino-3-O- {l-1 ( D-1-carbamoyl-3-to arboxymethyl-phenyl-carbamoylmethyl -2-deoxy-B-glucose, 2-benzoylamino-3-, (0-1-carbamoyl-3-carboxymethyl-phenyl-carbamoylmethyl-2-deoxy-B-glucose, 2 -Benzamino-3-O-L-1- (D--carbamoyl-3-carbox-propyl) -carbamoyl-2-methyl carcamptoethylJ-Carbamoylmethyl} -2-deoxy-5) -glucose, 2-benzamino-3-0 l-1-: - (D-1-k rbamoil karboksiprodil-W-carbamoyl-2-hloretil2 carbamoylmethyl -2-deoxy-1) -glucose, 2-acetamido-3-0- {1- o-X. -1- (D-1-carbamoyl-3, 3-dicarboxypropyl) -carbamoylethyl -carbamoylethyl -2-deoxy-1) -glucose, 2-, (beta-carbomethoxy succinamido) -Z-0-fb-1- (0 -1-carbamoyl-3-carboxypropyl) -carbamoylethyl} -carbamoylmethyl} -2-deoxy-B-glucose, 2- (beta-carbomethoxy succinamido) -3-0-o-1-b-1- (0-1 -carbamoyl-3-carboxypropyl) -carbamoyl ethyl -carbamoyl ethyl 2-deoxy-B-glucose 2-benvine-3-0- (C-1- (O-1-carbamoyl
-3-trimethylsilylcarboxypropyl (L) -carbamoyl ethyl -Carbamoylmethyl 5-2 deoxy-1, 4,6-tris-trimethyl (or 1) glucose (in contact with water, the trimethylsilyl ester groups quickly became hydrated), 2-acetamino-2 - disrksi-3-Of - (D-1-carbamoyl-3-trimethylsilyl-carboxypropyl) -carbamoylethyl-Carbamoylmethyl -1,4,6-tris-trimethylsilyl-B-glucose, 2-acetamino-3-0-Dl-tL - l- (Dl-carbamoyl-3-carboxGypropol) -carbamoylpropyl 3 -carbamoylethyl -2-deoxy-T) -glucose, 2-acetamino-3-0-p-1-L-1- (D-1-carbamoyl-3 -carboxypropyl) -carbamoyl-2 -oxypropyl) -carba myethyl -2-deoxy-B-gl1rkozy, 2-acetagolino-3-0-0-1-1 - L- (O-1-car-, .amoyl-3-carboxyproyl) -carbamoyl-2- (p-hydroxyphenyl) -ethyl-carbamoylethyl) -2-deoxy-B - glucose, 2-acetamino-3-0- {o-1- ь-1- (0-1-carbamoyl-Zgcarboxypropyl) -carbamosht-S, N-tetramethylene -carbamoylethyl-2-deoxy-B-glucose, 2-glycolylamino- 3-0-O-1-L-1- {O-1-carbamoyl-3-carboxypropyl) -carbamoylethyl-carbamoylethyl -2-deoxy-B-glucose, 2-glycolylamino-3-0-b-1t (O- 1-carbamoyl-3-carboxypropyl) -carbamoyl ethyl -carbamoylmethyl -2-deoxy-D-glucose, 2- (N-methylacetamino) -3-0- {LI- (DI-carbamoyl-3-carboxypropyl) -carbamoyl ethyl-carbamoylmethyl j .-2 -deoxy-B-glucose, 2- (N-methylacetamino) -3-0-Dl-Ll- (D-lcarbamoyl-3-carboxypropyl) -carbamoyl ethyl -carbamoylethyl -2-deoxy-D-glucose, 2-acetamio-3 -0- D-1- -1- (O-1-carbamoyl-3-carboxypropyl) -carbamoyl-2-phenylethyl-carbamoylethyl -2-deoxy-B-glucose, 2-acetamino-3-0- {Сь-1 - (0-1-carbamoyl-3-carboxypropyl) -carbamoyl I-2 - (p-hydroxyfeil) -ethyl-carbamoylmethyl -2-deoxy-B-glucose, 2-gschetamin6-3-0- ((L-1-carboxyethyl ) -carbamoyl-3-benzylcarboxypropyl-3-carbamoyl ethyl-carbamoylmethyl-2-deaoxy-T) -glucose, 2-acetamino-3-0- {tL-l- (Dl, 3-dicarboxypropyl) -Y-methylcarbamoyl ethyl -carbayoylmethyl -2-deoxy-B-glucose,
Example 28  By analogy with the method described in Example 3, sheep erythrocyte membranes linked to 2-acetamino-3-0- {0-1-carbamoyl-3-carboxypropyl) -carbamoylmethylT-N-methylcarbamoylmethyl3-2-deoxy- Y-glucose, 2-benzoylMino-3-0- {t {Dl-carb amoyl-3-carboxypropyl) -carbamoylmethyl -N-methylcarbamoylmethyl} -2-deoxy-B-glucose, 2-acetamine0-3-0-L- 1- {D-1-carbamoyl-3-kaE boxypropyl) -ca rbamoylethyl-Y-ethylcarbamoylmethyl -2-deoxy-D-glucose,. 2-acetamino-3-0-LI- - (D-1-carbamoyl-3-carboxypropyl) -carbamoylpropyl; -Y-methylcarbamoylmethyl -2-deoxy-B-glucose, 2-aceto 1 1-3-0- (: , -1- (0-1-carbamoyl-3-carboxypropyl) -carbamoylpropyl. -M-ethylcarbamoylmethyl -2-deoxy-Y-glucose, 2-benzamido-3-0-HL-I- - (D-1-carbamoyl-3-carboxypropyl) -carbamoyl-propyl-m-ethylcarbamoyl -2-deoxy-1) - glucose, 2-acetamino-3-O-EH-l- (Dl-carbamate-3-canister.  Cipropyl) -carbamoyl ethyl} -N-propylcarbamoylmethyl-2-des-oc-Si-D-glucose 2-acetamio-3-0-L-1- (0 1-carbamoyl-3-carboxypropyl) -carbamoyl-K, Pypenmethylene T-carbamoylmethyl 2-deoJ SECH-glucose 2-benzoyl a and no-3-j-L-1- (D-1-carbamyl-3-k arboxypropyl) -carbamoyl-S, M-penmethylene-carbamoylmethyl-2-deoxy-0-glucose , 2-acetamino-3-0-Ts-1- (D-1-carbamoyl-3-carboxypropyl) -Y-methi-carbamoylethyl-carbamoylmethyl-5-2-deoxy-O-glucose, 2-acetamino-3-0-D- 1- | (D-1-carbamoyl-3-carboxypropyl) -carbamoylmethyl-Y-methylcarba moethyl -2-deoxy-15-glucose, 2-benzoylamino-3-0- {o-1- (0-1-carba moyl-3- carboxypropyl) -carbamoylmethyl | -Y-methylcarbamoyl ethyl-2-deox-0-glucose, 2-sschetamino-3-0-o-1-b-1- (D-1-carb, g1moyl-3-carboxypropyl) -carbamoyl-ethyl-N-ethylcarbamoyl ethyl - 2-deoxy-0-glucose, 2-acetamino-3-O (D-1-carbamoyl-3-carboxypropyl) -carbamoylpropyl) -N-methylcarbamoyl ethyl -2-deoxy-P-glucose, 2-acetamino-3-0- {1 -1- - L-rl- (Di-carbamoyl-3-carboxypropyl) -carbamoylpropyl-N-ethylcarbamoylmethyl -2-deoxan-D-glucose, 2-benzamIdo-3-0-o-1-i-1 - (O-1-carba moyl-3-carboxypropyl) -carbamoylpropyl -Y-ethylcarbamoylethyl-2-dez in si-O-glucose, 2 acetamino-3-0- {o-1 -tb-1- {Dl-carbamoyl- Z-carboxypropyl) -carbam iletil-N-propilkarbamo iletilj-2-lesoki 7, iz-oz, ами м ap ap н м м}}} н т т e | | | | | | | ти ти ти ти e e e e e e e e e e e e e e e e e e e e a a a a a a a a a e e e a a e a e e e e e 2-deoxy-P-glucoeoi, 2-benzoylamino-3-0- | 1Ь-1-1Ь-1- (1 -1-carbamoyl-3-car boksipropil) -carbamoyl-S, N-Penta1 utilen2-carbamoylethyl 3 -2 -deoxy-B-glucose 2-acetamino-3-0-n 1-jb-1- (O-1-carbamoyl-3-carboxypropyl) -Y-methylcarbamoyl-carbamoyl and ethyl 5-2-deoxy-1) -glucose, 2 -acetamino-3. -0-C; l-1- (o-1-carbamoyl-3-.  -carboxymethylphenyl -carbamoylmethyl) -2-deoxy-TZ-glucose, 2-benzoyl in 3 but 3-0- {-1- (O-1-carbamoyl-3-carboxymethylphenylJ) -carbamoylmethyl} -2-deoxy-B-glucoea, 2 -benzamino-3-0-Cb-1 (O-1-carbamoyl-3-carboxypropyl) -carbamoyl-2-methylmercaptoethyl 2-carbamoylmethyl 3-2-deoxy, -P-glucose, 2-benzamino-3-0- 1: L-1- (o-1-carbamoyl-3-carboxypropyl) | -carbamoyl-2-chloroethylJ-carbamoylmethylT-2-deoxy-1) -glucose, 2-acetamino-3-0- {o-1- | L-1- (O-1-carbamoyl-3, 3-dicarboxypropyl) -carbamoylethyl-J-carbamoylethyl 5-2-desoxy-D-glucose, 2- (beta-carbomethoxy succinamido) -3-0 - ((O-1-carbamoyl, -3-carboxypropyl) -carbamoyl ethyl -carb amoylmethyl -2-de-zoxy-B-glucose, 2- (beta-carbomethoxysuccinamido) -3-0- {o-1-C-1- (B-1-carbamoyl-3 -carboxypropyl) -carbamoyl ethyl-carbamoylethyl j -2-deoxy, T) -glucose, 2-benzamino-3-0-Cy-1- (O-1-carbamoyl-3-trimethylsilylcarboxypropyl) -carbamoyl ethyl carbamoylmethyl -2 -1, 4,6-Tris-trimethylsilyl-D-glucose (when in contact with water, trimethylsilyl ester groups are fast washed), 2-.  -acetamino-2-deoxy-3-0-1-l- (Dl-carbamate-3-trimethylsilylcarboxypepropyl) - 0-1-fL-i- (D-1-carbamoyl-3-carboxypropyl) -carbamoylpropyl 3-carbamoylethyl -2-deoxy-D-glucose, 2-acetamino-3-0-fD-1-Ll- (D- carbamoyl-3-carboxamide) -carbamoyl-2-hydroxypropyl -carbamoylethyl -2-deoxy-B-glucose, 2-acetamino-3-0-o-I-L-1- (D-1-carbamoyl-3-carboxypropyl) -carbamoyl-2-p-hydroxyphenyl / -ethylZ-carbamoylethyl -2-deoxy-B-glucose, 2-acetamino-3-0-o-1-G1-1- (D-1-carbamoyl-3-carboxypropyl) - Carbamoyl-N, N-tetramethylene-carbamoyl methyl -2-deoxy-1) -glucose, 2-glycolylamino-3-0-Dl-Ll- (Dl-carbamoyl-3-carboxypropyl) -carramoyyleJ J-carbamate-2-deoxy-B-glucose, 2-glycolylamino- H-O-L-1- (O-1-carbamoyl-3-carboxypropyl) -carb oylmethyl-3-deoxy-1} -glucose, 2- (H-methylacetamino) -3-0-J fL-1- ( O-1-carbs1-moyl-3-carboxypropyl) -carbamoyl ethyl -carbamoylmethyl -2-deoxy-B-glucose, 2- (N-methylacetamino) -3-0- {Dl-Ll- {Dl-Kap6amoyl-3-carboxypropyl) - Carba 1 "Eylethyl} -carbamoyl ethyl 5-2-deoxy-1) -glucose, 2-acetamino-3-0-Dl-tL-1- (Dl-carbamoyl-3-carboxypropyl) -carbamoyl-2-phenylethyl 3-carbamoyl ethyl} -2 -dec6-1) -glucose oh, 2-acetamino-3-O- 0 1 (O-1-carbamoyl-3-carboxypro saws) -carbamoyl-2 - (n-. hydroxyphenyl) ethyl -carbamoylmethyl -2-deoxy-D-glucose, 2-acetamio-3-0- {tL-1- (D-1-L-1-carboxyethyl-carbamoyl-3-benzylcarboxypropyl,) -carbamoylethyl-carbamoylmethyl } -2-deoxy-and-glucose, 2-acetamino-3-0- {СЬ- 1- (Dl, 3-dicarboxypropyl) -N-methylcarbamoyl-methyl-carbamoylmethyl-2-.  -deoxy-O-glucose.  P p and m ep 29, By analogy with the method described in example 4, the group C of the polysaccharide Neis-ser a meningltidis is obtained, linked to 2-acetamino-3-O- (D-1-carbamoyl-3-carboxypropyl) -carbamoylmethyl -Y-methylcarbamoylmethyl1 -2-deoxy-C glucose, 2-benzoylamino-Z-O- | (D-1-carbamoyl-3-carboxypropyl) -carbamoylmethyl-N-methylcarbamoylmethyl -2-deoxy-B-glucose, 2-acetomino-3-O tL-l (D-1-carbamoyl-3-carboxypropyl) -carbamoyl ethyl -N-ethylcarbamoylmethyl -2-deoxy-B-glgkozoy, 2-acetamino-3-0- (CL-1- - {Dl-carbamoyl-3-carbox-glycanoyl-propyl-N-methylcarbamoylmethyl-2-eoxy-B 2-acetomino-3-O-- Ll- (Dl-Kap6 amoyl-3-carboxypropyl) -carbamoylpropyl N-ethylcarbamoylmethyl -2-deza) xy-B-glucose, 2-benzamido-3-O-L-1- - (P-1 carbamoyl-3-carboxypropyl) -carbamoylpropyl-N-ethylcarbamoylmethyl -2-deoxy-1) -glucose, 2-acetamino 3-0- | (D- -carbamoyl-3-carboxamideprop) -carbamoylethyl-N-propylcarbamoylmethyl5-2-deoxy-B-glucose, 2-acetamino-Z-O- I. -1- - (O-X-carbamoyl-3-carboxypropyl) -carbamoyl-N, L-pentamethylene -carbamoylmethyl | -2-deoxy-T) -glucose, 2-benzoclamino-3-0-L-1- (D-1-carba moyl-3-carboxypropyl) -carbamoyl-S, H-pentamethylene-carbamoylmethyl -2-deoxy-J - glucose, 2-acetamino-3-0- t, -I - (D-.  1-carbamoyl-3-carbox propyl) -m-methylcarbamoylethyl} -carba moylmethyl -2-deoxy-B-glucose, 2-acetamino-3-0-0-1-C (O-1-carbamo-Z-carboxypropyl) -carbamoylmethyl | -Y-methylcarbamoyl ethyl-2-deoxy-T) -glucose, 2-benzoylamino-3-0- {P-1 - - (D-1-carbamoyl-3-carboxypropyl) -carbamoi. pmethyl-N-methylcarbamoylethyl-2-dazoxy-D-glucose, 2-acetamino-3-0- {o-1-gb-1- (p-1-carbamoyl-3-carboxypropyl) -carbamoylethyl-y-ethylcarbamoylethyl-2 -deoxy-1) -glucose, 2-acetamino-3-0-B-1-LI- (Dl-carbamoyl-3-carboxypropyl) -carbamoylpropyl-M-methylcarba. milethyl -2-deoxy-& glucose, 2-acetamino-3-0-o-1-i-1- (n-1-carbamoyl-3-carboxypropyl) -carbamoyl-f propyl y-M-ethylcarbamo and lymeti-2 -deoxy-D-glucose, 2-benzamido-3-O-Go-1 H-1- (O-1-Carbamoyl-3-carboxylpropyl) -carbamoylpropyl-K ethylcarbamoylethyl -2-deoxy-1) -glucose, 2- acetamino-3-O-D-1- (0-1-carbamoyl-3-carboxypropyl) -carba. MyethylZ-N-propylcarbamoyl-methyl-2-deoxy-1) -glucose, 2-acetamino-3-O-o-1-1-1- (0-1-carbamoyl-3-carboxypropyl) -carbamoyl-Y, M-pent . Amethylene -carbamoylethyl -2-deoxy-T) -glucose, 2-benzoyl but-3-0- {o-1-Ü-1- {0-1-carbamoyl-3-carboxypropyl) -carbg NO. HN, N -PentaneTHneHJ-carbamoylethyl -2-deoxy-D-glucose, 2-acetamino-3-0-o-1-b-1- (B-1-carbamoyl-3-carboxypropyl) -N-methylcarbamoylethyl} -carbamoyl ethyl -2- deoxy-o-glucose, 2-acetamino-3-0-b-1- (o-1-carbamoyl-3-.  - to arboxyme, tilphenyl) - to arb amoylmetic -2-deoxy-1) -glucose, 2-benoylylamy no-3-0-L-1- (O-1-carba-moyl-3-carboxymethylphenyl) -carbamoylmethyl -2- deoxan-B-glucose, 2-benzamino-3-O-1-1- (0-1-carbamoyl-3-carboxypropyl) -carbamoyl-2-methylmercaptoethyl} -carbamoylmethyl -2-deoxy-P-glucose, 2-benzamino -3-0-Tsb-1- (0-1-carbamoyl-3-carboxypropyl) -carbamoyl-2-chloroethyl-carboxymonoylmethyl -2-deoxy-B-glucose, 2-acetamino-3-0-h-1-h -1- (O-1-carbg1moyl-3,3-dicarboxypropyl) -carbamoylethyl} -carbamoylethyl -2-deoxy-L-glucoeoy, 2- (beta-carbomethoxy succinamindo) -3-0--1- {O-1 -carbamo L-3-carboxypropyl), -carbeoyloyl-ethyl-carbamoylmethyl -2-deoxy-1) -glucose, 2- (beta-carbomethoxy succinate) -3-0-) -1- {| L-1- (O-1-carbamoyl- 3-carboxypropyl) -carbamoylethyl-carbamoylethyl-2-deoxy-B-glucose, 2-benamine-3-O- {. B-1- (0-1-carbamoyl-3-trimethylsilylcarboxypropyl) -carbamoyl ethyl -carbamoylmethyl -2-deoxy-1, 4,6-tris-trimethylsilyl-0-glucoea (when in contact with water, the trimethylsilyl ester groups are quickly washed with oily) 2-acetamino-2-deoxy-3-0-: Cb-1- (B-1-carbamoyl-3-trimethylsilycarboxypropyl) -carbgilonl Ethyl-carbamoylmethyl -1, 4,6-tris-trimethylsilyl-B-glucose, 2-acetamino -3-0- {o-1-b-1- (o-1-carbamoyl-3-carboxypropyl) -. carbamoylpropyl -carbamoylethyl -2-deoxy-B-glucose, 2-acetamino-3-0-o-1-L-1- (0-1-carbamoyl-3-carboxypropyl) -car6amoyl-2 -oxypropyl-carbamoyl ethyl -2- deaoxy-1) -glucose, 2-aceto # 1Ino-3-0-o-1-1-1- {O-1-carbamoyl-3-carboxypropyl) -carbamoyl-2 - (p-oxyphenyl) -ethyl-carbamochlethyl -2-deoxy-D-glucose, 2-acetamino-3-0-o-1-l-1- (O-1-carbamoyl-3-carboxypropyl) -carbamoyl-N, N-tetramethylene -carbamoylethyl g2-leoxy- D-glucose, 2-glycrylamino-3-O- {O-1-1-1- (O-1-carbamoyl-3-carvoxypropyl) -carbamoylethylJ-carbamoylethyl / A-2-deoxy-B-glucose, 2-glycolylamino - 3-0- - (D-1 -carbamoyl -Z-carboxypropyl) -carbamoylethyl -carbamoylmet. Il-2-deoxy-1) -glucose, 2- (L-Methylacetamino) -3-0-L-1- (D-1-carbamoyl-3-carboxypropyl) -carbamoyl ethyl-carbamoylmethyl -2-deoxy-D-glucose , 2- (N-methylacetamino) -3-0-P-1-Gb-1- (P-1-carbgshoyl-3-carboxypropyl) -carbamoylethyl-D-carbamoylethyl -2-deaxis-O-glucose | 2-acetamino-3-0-o-1-LI- (D-1-carbamoyl-3-carboxypropyl) -carbamoyl-2-phenylethyl-carbamoylethyl} -2-deoxy-D-glucose, 2-acetamino-3-0 -f L-1- (Dl-carbamoyl-3-carboxypropyl) -carbamoyl-2 - (p-hydroxyphenyl) -ethyl-carbamoylmethyl -2-deoxy-O-glucoeoy, 2-acetamino-3-0-C1 -1- D-1- (L-1-carboxyethyl) -carbamoyl-3-benylcarboxypropyl -carbamoyl ethyl-3-carbamoylmethyl -2-deoxy-1} -glucose, 2-acetamino-3-0-f Ll- (D-lf3-dicarboxypropyl) - N-methylcarbamoyl ethnylcarbamoylmethyl5-2-deoxy-B-glucoeoi, Example 30, By analogy with.  PBasmodium knowfesi merozoites, associated with 2-acetamino-3-0-C (OH-carbamoyl-3-carboxypropyl) -carbamoylmethyl -methylcarbamoylmethyl -2-deoxy-D-glucose , 2-benzoylamino-3-O-f (D-1-carbamoyl-3-carboxypropyl) -carbamoylmethyl} -N-methylcarbamoyl-.  methyl -2-deoxy-0-glucose, (2-acetamino-3-O-f L-l- {D-l-carbamoyl-3-carb. QKCipropyl) -capbamoylethyl -Y-ethylcarbamoylmethyl -2-deoxy-1 -glucose, 2-acetamino-3-0- {--1- (Dl-carpamoyl-3-cansopiopropyl) -carbamoylpropyl-3-cane-3-cannabisypropyl) -carambamoylpropyl-3-cannibalo-3-cannabisoppil) deoxy-B-glucose, 2-acetamine-3-0-C L-1- (D-1-carbamoyl-3-carboxypropyl) -carbamoylpropyl -Y-ethylcarbamoylmethyl-2-deoxy-0 glucose, 2-benzamido-3- 0-L-1- (D-1-carbamoyl-3-carboxypropyl) -carbamoylpropyl -Y-; 9til1 {arbamoylmethyl -2-deoxy-1) -glucose, 2-acetomino-3-0-1-1- ( O-1-carbamoyl-3-carboxypropyl) -carbamoylethyl} -N-propylcarbs1-moylmethyl -2-deoxy-O-glucose, 2-acetamine-3-0-f L-1- {0-1-carbamoyl-3-carboxypropyl carbamoyl-N, N-pentamethyl carbamoyl methyl t-2-deoxy-D-glucose, 2-bin; Zoyl "1-3-0-K-1- (D-1-carbamoyl-3-carbrxypropyl) -carbamoyl-N, N-pentamethylene-J-carbamoylmethyl 3 -deoxy-O-glucose, 2-acetamino-3-O-ffL-1 - (C-1-carbamoyl-3-carboxy-propyl) -Y-methylcarbamoyl ethyl -carbamoylmethyl -2-deoxy-0-glucose, 2-acetamino-3-0-O-1-t Dl-Kap6aMoen-3-carboxypropyl) - carbamoylmethyl-N-methylcarbamoylethyl -2-deoxy-ib-glucose, 2-benzylamino-3-0-0-1-pD-1-carbamoyl-3-carboxypropyl} -carvamoylmethyl -N-methyl-carbamoyl ethyl -2-deoxy-D-glucose, 2 -acetamio-3-0-o-1-1i-1- (O-1-carbamoyl-3-carbroxypropyl) -carbamoylethyl -N-ethylcarbamoylethyl 3 -2-deoxy-1) -Glucose, 2- cetamino-3-0-o-1-b-1- (p-1-carbamoyl 73-carvoxypropyl) -carbamoylpropyl -N-methylcarbamonylethyl -2-desoxy-b-glucose, 2-acetyamo-3-0- {p- 1-Ll- {Dlj ap6a1-moyl-3-carboxypropyl) -carbamoylpropyl} -Y-ethylcarbamoylmethyl-L-2-deoxy-O-glucose, 2-benzamido-3-0- {b-1-b-1- (0-1- carbamoyl-3-carboxypropyl) -carbamoylpropyl-N-ethylcarbamoylethyl-2-deoxy-J-glucose, 2-acetamino-3-0-o-1-1-1- (0-1-carbamoyl-3-carboxypropyl) -carbamoylethyl -N-propylcarbamoylethyl -2-deoxy-B-glucose, 2-acetamino-3-0-D-1---G-CO-T-carbamoyl-3-carboxypropyl) -carbamoyl-N, N-pentamethylene-carbamoyl ethyl -2- Esoxy-T) -glucose 2-benzoylamino-3-0-o-1-b-l- {DI-carbamoyl-3-carbox-propyl) -carbamoyl-N, N-pentamethylene 3 -carbg1 moeethyl -2-deoxy-0-glucose, 2-acetamino-3-0-Dl-lL-l- (Dl-carbamate-3-carboxopropyl) -Y-methylcarbamoylethylJ-carbamoylethyl -2-deoxy-TZ-glucose, 2-acetamino-3-0-Db-1- (D-1-carbamoyl-3-carboxymethylphenyl) -carbamoylmethyl -2-deoxy-glucose, 2-benzoylamimo-3-0-1- (D-1-carbamoyl-3-carboxymethylphenyl-carbamoylmethyl -2-deoxy- 1) - glucose, 2-benzamino-3-0- {. Ll- {D-1-carbamoyl-3-carboxypropyl} -carbamoyl-2-methylmercaptoethyl-carbamoylmethyl -2-deoxy-B-glucose, 2-benzamino-3-O- (o-1- (0-1-carbamoyl- 3-carboxypropyl) -carbamoyl-2-chloroethyl-carbamoylmethylT-2-deoxy-B-glucose, 2-acetamino-3-0-o-1-1-1- (O-1-carbamoyl-3,3-dicarboxypropyl) -carbamoyl ethyl -carbamoylethyl 5-2-deoxy-T) -g-lucosis, 2- (beta-carbomethoxy-succinamido-3-0- {b-1- (B-1-carbamoyl-3-carboxypropyl) -carbamoylethyl-carbamoylmethyl -2- deoxy-B-glucose, 2-beta-carbomethoxysuccinamido) -3-0- {o-1-Ll- {Dl-carbamoyl-3-carbox-propyl) -carbamoyl uthyl} -carbamoylethyl} -2- Esoxy-13-glucose, 2-benzamino-3-0-1- {D-1-carbamoyl-3-trimethylsilylcarboxypropyl) -carbamoylistil} -carbamoylmethyl -2-deoxy-1, 4,6-tris-trimethylsilyl-O -glucose (upon contact with water, the trimethylsilyl ester groups are rapidly washed off), 2-acetamio-2-deoxy-3-0-b-1- (D-1-carbamoyl-3-trimethylsilylcarboxypropyl) -carbamoyl ethyl -carba. Moylmethyl -1,4,6-tris-trimethylsilyl-D-glucose, 2-acetamino-3-0-D-1 "- Ll- (Di-carbamoyl-3-carboxy-propyl) -carbamoylpropyl-carbamoylethyl -2-deoxy- T) -glucose, 2-acetamino, -3-0-p-1-l-1- (0-1-carbamoyl-3 | -carboxypropyl) -carbamoyl-2-oxy | propyl-carbamoylethyl -2-deoxy - - glucose, 2-acetamino-3-D-1-L-1- {D-1-carbamoyl-3-carboxypropyl) -carbamoyl-2 - (p-hydroxyphenyl) ethyl-carbamoyl ethyl -2-deoxyglucose 2-acetamino -Z-O-b-1 Ll-D-1-ka bamoyl 3-carboxypropyl) -carbamoyl-S, N-tetramethylene -carbamoyl ethyl -2-deoxy-0-glucose, 2-glycolylamino-3 0 Dl b-1- (0-1-carbamoyl-3 carboxypropyl) -carbamoyl ethyl -carboylethyl -2-deoxy-glucose, 2 glycolylamino-3-0-L-1- (D-1-carbamoyl 3-carboxypropyl) -carbamoyl ethyl-carbamoylmethyl -2-deoxy-O-glucose F 2- (N- Methylacetamino) -3-0 1 (1) 1 carba oyl-3-carboxypropyl-dib) -carbamoylethyl-carbamoylmethyl -2-de8oxy-0-glucose, 2- (N-methylacetamino) -3-0-D-1-b- 1- {0-1-carba mil-3-carboxypropyl) -carbamoylethyl-carbamoylethyl -2-deoxy-glucose 2-acetam-but-3-0-D-1-L-1- {D-1-carbamoyl 3- carboxypropyl) -carbamoyl-2-phenylethyl-carbamoylethyl -2-deoxy-O-glucose, 2-acetamino-3-OL-1-D-1-carbamoyl-3-carboxypropyl) -carbamoyl-2 - (p-ca iphenyl) -ethyl-carbamoitmethyl-2-deoxyglucose 2-acetamino-Z-O-L-1- (D-1-Li-Karboxyethyl-carbamoyl-3-benzylcarboxypropyl) -carbamoyl ethyl carbamoyl methyl -2-deoxy-glucose, 2-acetomino-3-O-L-1- (D-1,3-dicarboxypropyl) -N-methylcarbamoyl ethyl -carbamoylmethyl -2-reoxy-B-glucose.  Example 31 By analogy with the method described in Example 6, CBA / J T-lymphoblasts of mice associated with 2-acetamino-3-O-f (D-1-carbamoyl-3-carboxypropyl) -carbamoylmethyl -Y are prepared. -methylcarbamoylmethyl} -2-det-zoxy-P-glucose, 2-benzoylamino-3 0- (L (Dl-carbamate-3-carboximpropyl-carbamoylmethyl / 5-H-methylcarbamoylmyl 2-deoxy-glucose, 2 acetamino-3-0-LI- (D-1-carbamonl-3-carboxypropyl) -carbamoylethyl-N-ethylcarbamoylmethyl -2-deoxy-0-glucose, 2-acetamino-3-0- (O-1-carbamoyl-3 -carboxypropyl) -carbamoylpropylZ-N-methylcarbamoylmethylZ-2-deoxy-B-glucose, 2-acetamino -Z-O-1- (0- 1-carbamoyl-3-carboxyp13opyl) -carbamoylpropyl -N-ethylcarbamoylmethyl} -2-deoxy-0-glucose,) 2-benzamido-3-0-b-g1- (( 0 1-carbamoyl-3-carboxypropyl) -carbamoylpropyl-N-ethylcarbamoylmethyl) -2-deoxy-p-glucose, 2-acetates but-3-O-lj-l- (Dl-carbamoyl-3-carboxypropyl) -carbamoylethyl - N-propyl carbamoylmethyl -2-deoxy-1) -glucose 2-acetamino-3-0-C L-1- (O-1-carbamoyl-3-carboxypropyl) -carbamoyl-S, H-pentamethylene-carbamoylmethyl -2- deoxy-P-gdpokozoy 2-benzoylamino-3-0 (0-1-carbamoyl-3-carboxypro saws) -carbsmoyl-s, N-pentamethylene -carbamoylmethyl --2-deoxy-TZ-g Lukozy, 2-acetamiyo-3-0- {L-1- (D-1-carbamoyl-3-carboxypropyl) -N-methylcarbamoylethyl - carbamoylmethyl) -2-deoxy-TZ-glucose, 2-acetamine-3-O- Dlj (Dl-carbamoyl-3-carboxypropyl) -carbamoylmethyl; --N-methylcarbamoylethyl -2-deoxy-3. 1-glucose, 2-benzoylamino-3-0-1 o-1- (D-1-carbamoyl-3-carboxypropyl) -carbamoylmethyl -N-methylcarbamoyl ethyl j-2-deoxy-D-glucose, 2-acetamino-3- 0-p-1- - {LI- {D-1-carbamoyl-3-carboxypropyl) -carbamoylethyl-N-ethylcarbamoylethyl) -2 deoxy-1) -glucose, 2-acetamino-3-O-o-1-b -1- (D-1-carbamoyl-3-carboxypropyl) -carbamoylpropyl -N-methylcarbamoylethyl-2-deoxy-1) -glucose, 2-acetamino-3-O-DI-LI- (D-1-carbamoyl-3 -carboxypropyl) -carbamoylpropyl -N-ethylcarbamoylmethyl-2-deoxy-0-glucose, 2-benzamido-3-O-D-1-L-1- (D-1-carbamoyl-3-carboxypropyl) -carbamoylpropyl-N- ethyl carbamoyl ethyl 3 -2-deoxy-O-glucose, 2-acetamino-3-O-Go-1-1-1- (G) -1-carbamoyl-3-carboxy propyl) -carbamoylethyl-N-propylcarbamoylethyl-2-deoxy- T) -glucose, 2-acetamino-Z-O-Go-1- | l-1- (O-1-carbamoyl-3-carboxypropyl) -carbamoyl-N, N-pentamethylenZ-carbamoylethyl -2-deoxy-1) - glucose, 2-benzoyllamino-3-O-fD-1-1- (B-1-carbamoyl-3-carboxypropyl) -carbamoyl-N, N-pentamethylene -carbamoylethyl -2-deoxy-T) -glucose, 2-acetamino-gz-0-1-1 -1-LI- (D-1-carbamoyl-3-carboxypropyl) y-methylcarbamoyl ethyl carbamoyl ethyl -2-deoxy-T) -glucose, 2-acetamino-3-0-1 -1- {O-1-carbamoyl-3-carboxymethylphenyl1 - arbamoilmetil} -2-deoxy-1) -glucose, 2-benzoylamino-3-0- b. d - {D-l-carb. amoyl-3-carcocimetilphenyl-carbamate-2 -2-deoxy-T) -glucose, 2-benzamino-3-0-11-1- (0-1-carbamoyl-3-carboxypropyl) -carbamoyl-2-methylmercapto-ethyl-carbamoyl -2-deoxan-B-gtpokozy, 2-benzamino-Z-O-PJ-I- (D-1-carbamoyl-3-carboxypropyl) -carbamoyl-2-chloroethyl-carbamoylmethyl -2-deoxy-T) -glucose, 2-adhetamine-3-0- ((P-1-carbamoyl-3, 3-dicarboxidropyl) -carbamoylethyl-carbamoylethyl -2-deoxy-B-glucose, 2- (beta-carbomethoxisuccinamido) -3-0- {. L- (D- -carbamoyl-3-carboxamide) -carbamoyl ethyl -carbamoylmethyl 3 -2-deoxy-P-glucose, 2 (beta carba toxisuccinamido) -3-0-1 -1 -1- 1 - (C-1 -carbamoyl-3-carboxypropyl) -carbamoyl ethyl-carbamoyl ethyl -2-deoxy-T) -glucose, 2-benzamino-3-0- {ili-l- (Dl-carbamoyl 3-trimethylsilylcarboxypropyl) -carbamoyl ethyl -carbamoyl methyl deoxy-1, 4, b, tris-trimethylsyl-P glucoea (when in contact with water, the trimethylclide ester groups are quickly immersed), 2-acetamino-2-deoxy-3-O-L-1- {O-1-carb-11oyl -3-trimethylsilylcarboxypropyl) -carbamoyl ethyl -carbamoylmethyl-1, 4,6-three -trimetilsilil-D-glucose, 2-acetamino-3-0- {D-1-
- L-1t- (o-1-carbamoyl-3-carboxypropyl) -carbamoylpropyl -carbamoylethyl -2-deoxy-T) -glucose, 2-acetamino-3-0-o-1-Le-1- (0-1 -carbamoyl-3-carboxypropyl) -carbamoyl-2 -oxypropyl -carbamoylethyl) -2-deoxy-1) -glucose, 2-acetamiyo-3-O-fo-1-
(Dl-carbamoyl-3-carboxypropyl) -carbamoyl-2 -oxypropyl -carbamoylethyl-2-deoxy-1) glhekose, 2-aueTaMHHo-3 0- {Dl-Ll- {D-1 -carbamoyl-3-carboxypropyl) -carbamoyl -2- (p-hydroxyphenyl) -ethyl-carbamoylethyl -2-dzok.si-B-glucose, 2-acetamino-3-0-O-1-1-1- (0-1-carbamoyl-3-carboxypropyl) -carbamoyl-S, H-t. tetramethylene -carbamoyl ethyl 5-2-deoxy-1) -glucose, 2-glycolylact-3-0- {o-1-b-1- (0-1-carbamoyl-3-carboxy. cypropyl) -carbamoyl ethyl} -carbamoylethyl | -2-deoxy-0-glucoeoy, 2-glycolylamino-3-0-b-1- (0-1-carbamoyl-3-carboxypropyl) -carbamoyl ethyl-carbamoylmethyl -2-deoxy- D-glucose, 2- (N-meth Ilacetamino) -3-0-LI- (D-1-carbamoyl-3-carboxy-propyl) -carbamoyl ethyl -carbamoylmethylT-2-deoxy-and-glucose, 2- (N-methyl-acetamino) -3-0-f.-l - (D-1-carbamoyl-Zukarboxypropyl) -carbamoylethyl-carbamoylethyl) -2-deoxy-D-glucose, 2-acetamino-3-0-o-1-L-1- (P-1-carbamoyl-3-carboxypropyl ) -carbamoyl-2-phenylethyl-carbamoyl ethyl -2-deoxy-T) -glucose, 2-acetamino-3-0-L-1- (D-1-carbamoyl-3-carboxypropyl) -carbamoyl-2 .- (p -oxiphenyl) -ethyl -carbamoylmethyl; -2-deoxy-1) -g10cbcd, 2-c-acetamio-3-0-fL- -QD-i- (Ll-carbox-ethyne) -carbamoyl-3-benzylcarbocpi-cQpyl-kbkbkbkbkbkbkbkbkbkbkbkbkbkbakbakbakbakbakbakbil-3-benzyl-3-benzyl-3-benzyl-3 C-P-glucose, 2-acetamylino-3-0-f L-1- (D-1,3-dicarboxypropyl) -K-methylcarbamoyl ethyl-carbamoylmethyl -2-deoxy-B-glucose. P and. meper 32, by analogy with the method described in example 12, receive the scapure vaccine (Beringwerke) associated with 2-acetamino-3-0-tCD-carbamoyl-3-carbox-propyl) -carbamoyl-methyl} -methylcarbamoylmethyl 5-2-deoxy -p-glucose, 2-benzoylamino-3-0- {(O-1-carbamoyl-3-carboxypropyl) -carbamoylmethyl -Y-methylcarbamoylmethyl -2-deoxy-1) -glucose, 2-aueTaMifHo-3-0-tL -l- (Dl-Kap6aMOHn-3-carboxypropyl) -carbamoylethylZ -Y-ethylcarbamoylmethyl} -2-deoxH: -) -glucose, 2-acetamino-3-0-GSY-l- (Dl-carbamate-3-carbox-propylpropyl) -carbamoylpropyl -N-methylcarbamoyl | methylZ-2-deoxy-p-glucose, 2-acet
; amino-3-0-Cy-1- (b-1-carbamoyl-37 -carboxypropyl) -carbamoylpropyl J-Y-ethylcarbamoylmethyl -2-deoxy-0-, -glucose, 2-benzamide-3-0- (b -1- (D-1-to rbamoyl-3-carboxypropi) -carbamoylpropid) -N-ethylcarbamoyl ethyl 5-2 desuxy-B-glucose, 2-acetamino-3-0-1-1- (0-1-carbamoyl- 3-carboxyp {) opil) -carbamoyl ethyl -Y-propylcarbamoylmethyl} -2-deoxy-T) -glucose, 2-cetamino-3-0-L-1- (D-.1-carbamoyl-3-carboxypropyl) -carbamoyl -N, N-pentamethylene -carbamoylmethyl -2-deoxy-P-glucose, 2-benzoylamino-3-0- {L-1- {O-1-carbamoyl-3-carboxypropyl.) -Carbamoyl-N, L-pentamethylene -carbamoylmethyl) -2-dvz xi-1) -glucose, 2-acetamno-3-0-G L-1- (0-1-carbamoyl-3-carboxypropyl) -N-methylcarbamoylethylJ-carbamoylmethyl -2-deoxy-0-glucose, 2-acetamine 3-0-b-1- {O-1-carbamoyl-3-carboxypropyl) -carbamoylmethyl -Y-methylcarbamoyl ethyl-2-deoxy-b-glucose, 2-benzoylamino-3-O-fo-l- (O-1- carbamoyl-3-carboxypropyl) -carbamoylmethyl -N-methylcarbamoylethyl -2-deoxy-p-glucose, 2-acetamino-3-0-o-1-l-1- (0-1-carbamoyl-3-carboxypropyl) -carbamoyl ethyl -N-ethylcarbamoylethyl -2-deoxy-1) -glucose, 2-acetamino-3-0-o-1-h-1- (B-1-carbamoyl-3-carboxypro | Peel) -carbamoylethyl-N-methylcarbamoyl 1-ethyl-2-deoxy-0-glucose, 2-acetamino-3-0-O-1-1-1- (B-1-carbamoyl-3-carboxypropyl) -carbamoylpropyl I -Y-ethylcarbamoylmethyl -2-deoxy | -1 ) -glucose, 2-benzamido-3-0-p-1-, (D-1-carbamoyl-3-carboxypropylcarbamoylpropsh-H-ethylcarbamoyl -2-deoxy-P-glucose, 2-acetamino-3- | D-1- 6-1- {L-1-carbamoyl-3-carboxypropyl) -carbamoylethyl-I-propylcarbamoylethyl} -2-deoxy-i-glucose, 2-acetamino-3-0-1 D-1 -. (D- 1-carbamoyl-3-carboxypropyl) -carbamoyl-N, N-pentamethylene -carbamoylethyl -2-deoxy-P-glucose, 2-benzoylamino-3-0- ((0-1-carbamoyl-3-carboxypropyl) -carbamoyl- N, N-Penta methylene -carbamoyl ethyl 3-deoxy-D-glucose, 2-acetamino-3-O-fo-1-LI- (Dl-carbamoyl-3-carboxypropyl) -N-methylcarbamoylethyl-carbamoylethyl -2-deoxy- o-glucose, 2-acetamino-3-0- (CB-1- (B-1-carbamoyl-3-. -carboxymethylphenyl-carbamoylmethyl) -2-deoxy-B-glucose, 2-benzoylamino-3- 0- (D-1 -carbamoyl-3-carboxymethylphenyl 7carbamoylmethyl -2-deoxy-B-glucose, 2-benzamino-3-0-f'-1- (I t-l-carbamoyl-3-canbixypropol) -carbamoyl- 2-methylmercaptoethyl -carbamoylmethylZ-2-deoxy-1) -glucose, 2-benzamine-3-0-LI: - (D-1-carbamoyl-3-carboxypropyl) -carbamoyl-2-hlrethyl) -carbamoylmethyl | -2- deoxy 1-1) -glucose, 2-acetam but-3-0-p-1-1-1- (0-1-carbamoyl-3,3-dicarboxypropyl) -carbamoyl ethyl-carbamoylethyl -2-deoxy-p-glucose 2 - (beta-carbomethoxy succinamido) -3-0-1-1- (P-1-carbamoyl-3-carbox propyl) -carbamoyl ethyl-carbamoyl methyl -2-deoxy-B-glucose, 2- (beta carbomethok isuktsinamido) -3-0- | o-1- (D-1-carbamoyl-3-carboxypropyl) -carbamoylethyl-carbamoyl ethyl -2-deoxy-B-glucose, 2-benzamino-3-0-b-1- (0-1-carbamoyl-3-trimeti silylcarboxypropyl) -carb "eylethyl-carbamoylmethyl -2-deoxy-1,4,6-tris-trimethylsilyl-T) -glucose (upon contact with water, the trimethylsilyl ester groups are quickly washed with c). , 2-acetamino-2-deoxy-3-0- (L- (D-1-carbamoyl-3-trimethylsilylcarboxypropyl) -carbamoyl ethyl-carbamoylmethyl -1, 4,6-tris-trimethylsilyl-D-glucose, 2-acetamine 3-0-o-1- (O-1-carbamoyl-3-ka.rboxypropyl) tkarbamoidpropyl -carbamoylethyl -2-deoxy-1) -glucose, 2-acetamino -3-0- {p-1-i-1 - {B-1-carbamoyl-3-car-boxypropyl) -carbamoyl-2-hydroxypropy-carbamoylethyl -2-deoxy-B-glgocozo 2-acetamino-3-O- {o-1-b-1- (B-1 -; carbamoyl-3-carboxypropyl) -carbamoyl-2- (p-hydroxyphenyl) -ethyl-carbamoyl ethyl -2-deoxy-13-glucose, 2-acetamino-3-O-o-1-b-1- (P- 1-carbamoyl-3-carboxypropyl) -carbamoyl-N, N-tetr Amethylene -carbamoyl ethyl -2-deoxy-B-glucose, 2-glycolylamine (O-1-carbamoyl-3-carboxypropyl) -carbamoyl ethyl-carbamoylethyl -2-deoxy-1) -glucose, 2-glycolylamino-3-0- { -1- (D-1-carbamoyl-3-car6oxypropyl) -carbamoyl ethyl -carbamoylmethyl -2-deoxy-1) -glucose, 2 -. (L-methylacetamino) -3-0 - b | -1- (0- 1-carbamoyl-3-carboxypropyl; -carbamoyletiJ-carbamoylmethyl -2-deoxy-1) -glucose, 2- (N-methylacetamino) -3-0- {o-1-i-1- (0-1-carba moyl-3-carboxypropyl) -carbamoylethyl -carbamoylethyl -2-deoxy-1) -glucose, 2-acetamino-3-O-fo-1- - pj-1- (D-1-to arbamoyl-3-to arboxyprocnito) -carbamoyl-2-phenyl Tyl-carbamoylethyl-deoxy-B-glucose, 2-acetamine-3-0-i L-1 - {D-1-carbamoyl-3-carboxypropyl) - carbamoyl-Z - (p-oxyphenyl) -ethyl-carbamoylmethyl -2 -deoxy-1) -glucose, 2-acetamino-3-0-Ll tD-l-L-1-carboxyethyl) i-to arbamoyl-3-benzylcarboxypropyl) -carbamoylethyl-carbamoylmethyl -2-deoxy-I-glucose, 2-acetone1 Mino-3-0-tLi-l- (Dl, 3-dicarboxypropyl) -N-methylcarbamoyl ethyl -carbamoylmethyl | -2-deoxy 1) -glucose. Example 33. By analogy with the method described in Example 17, a rabies nose vaccine (Beringwerke) linked to 2-acetamino-3-O-D-1 -carbamoyl-3-carboxypropyl) -carbamoylmethyl -N-methylcarbamoylmethyl -2-deoxy-1) -glucose, 2-benzoylamino-3-0- (D-1-carbamoyl-3-carboxypropyl) -carbamoylmethyl-y-methylcarbe1moylmethyl -2-deoxy-E-glucose, 2-acetamine-3- 0- | l-1- - (D-1-carbamoyl-3-carboxypropyl) -carbamoyl ethyl -N-ethylcarbamoylmethyl -2-deoxy-1) -glucose, 2-acetamino-3-O- | L-1- (D-1-carbamoyl-3-carboxypropyl) -carbamoylpropyl -N-methylcarbamoylmethyl -2-deoxy-D-glucose, 2-acetamino-3-0-f L-1- (D-1-carbamoyl -Z-carboxypropyl) -carbamoylpropyl -N-ethylcarbamoylmethyl -2-deoxy-and-glucose, -2-benzamido-3-0-L. -I- (DI-carbamoyl-3-carboxypropyl) -carbamoylpropyl -N-ethylcarbamoylmethyl - 2-deoxy-E-glucose, - 2-acetamino-3-0- | L-1 - - (D-1-carbamoyl-3-carboxypropyl) -carbamoyl ethyl -Y-propylcarbamoylmethyl -2-deoxy-1) -glucose, 2-acetamino-3-0-1- (0-1-carbamoyl -3-carboxypropyl) -carbamoyl-N, N-pentamethylene -carbamoylmethyl -2-deoxy- | ) -glucose, 2-benzoylamino-3-O-fL-1- (D-1-carbamoyl-3-carboxypropyl) -carbamoyl-N, N-pentamechylene -carbamoylmethyl -2-deoxy-B-glucose, 2-acetamine Z-O-L-1- (D-1-carbamoyl-3-carboxypropyl) -N-methylcarbamoyl ethyl -carbamoylmethyl -2-deoxy-B-glucose, 2-acetamino-Z-0-Go-1- (D-1 -carbamoyl-3-carboxypropyl) -carbamoylmethyl -N-methylcarbamoylethyl -2-deoxy-T) -glucose, 2-benzoylamino-3-0- {o-1-t (Dl-carbamoyl-3-carbox-propol) -carbeinoylmethyl -methylcarbamoylethyl -2-deoxy-D-glucose, - / 2-acetamino-3-0-fo-l-, - L-1- (D- 1-carbg1MOyl-3-carboxypropyl) -carbamoylethyl -N-ethylcarbamoylLethyl -2-deoxy-1) -glucose, 2-ace-, amino-3-0-v-1-1-1- (D-1-carbamoyl-3-carbox-propyl) -carbamoylpropyl-N-methylcarbamoylethyl -2 -deoxy-1) -glucose, - 2-acetamino-3-0-P-1- (B-1-carbamoyl-3-carboxypropyl) -carbamoylpropyl -N-ethylcarbamyl, methylmethyl -2-deoxy-T) -glucose , i 2-benzamido-3-0-o-1-l-1- (O-1-car; bamoyl-3-carboxypropyl) -carbamoylpropyl-N-ethylcarbamoylethyl -2-deoxy-B-glucose, 2-acetamine- 3-0-p-1-l-1- (p-1-carbam6yl-3-carboxypropyl) -carbamoylethyl-N-propylcarbamoylethyl -2-deoxy-t) -glucose, 2-acetamino-3-0-o-1 -1l-1- (0-1-carbamoyl-3-carboxypropyl) -carbamoyl-N, N-pantamet ilen -carbamoyl ethyl -2-deoxy-1) -glucose, 2-benzoylamino-3-0-fD-l-Ll- (D-1-carbamoyl-3-carboxy-Sipropyl) -carbamoyl-N, N-pentamethylene-carbamoylethyl-2 -deoxy-O-glucoey, - 2-acetamino-3-0- 0-1, - | 1-1- (0-carbamoyl-3-carboxypropyl) -Y-methylcarbamoyl ethyl 7-carbamoylethyl -2-deZoxy-glucose, 2 -acetamino-3-0-l- 1- (0-1-carbamoyl-3-carboxymethylphenyl -carbamoylmethyl -2-deoxy-O-glucoea, 2-benzoylamino-3-0- (L-1- (0-1 carbamoyl -3-carboxymethylphenyl} -carbamoylmethyl-2-deoxy-B-g of lucoeoi, -2-6683 amino-3-0-tL l (D l carbamoyl-3-carbamide-propyl) -carbamoyl-2-methyl mercaptoethyl-carbamoylmethyl -2-de zoxy-D) -glucose, 2-benzamino-3-0-L-1- (D-1-carbamoyl-3-carboxypropyl) -carbamoyl-2-chloroethyl-3-carbamoylmethyl -2-deoxy-1) -glucose, 2- acetamino-3-0 (D-1-carbamoyl-3,3-dicarboxypropyl) -carbamoyl and ethyl -carbamoylethyl1-2-deoxy-1) -glucose, 2- (beta carbomethoxysuccinamido) -3-0-Dl-Ll- (Dl -carbamoyl-3-carboxamide) -carbamoylethyl -carbamoylmethyl -2-deoxy-B-glucose, - 2- (beta, a-carbomethoxy-succinamido) -3-0- (b-1-1-1- (O-1-carbamoyl -3-carboxypropyl) -carbamoylstil -carbamoylethyl at-2-deoxy-T) glucose, 2-benzamino-3-0-1- {C-1-carbamoyl-3-zhrymethylsilylcarboxypropyl) -carbam ethyl carbamoylmethyl | -2-deoxy-1, 4, b-7gris-trimethylsilyl-P-glucose (when in contact with water, trimethyl silyl ester groups are quickly washed, 2-acetamino-2-deoxy-3-0-ft -l- {Dl- carbamoyl-3-trimethyl-silylcarboxipropyl) -carbamoylethyl3 -carbamoylmethyl -1,4,6-tris-tr-imethyl silyl-glucose, 2-acetamino-3-O- | p-1-I Ll- (Dl-carbamate-3-carbox propyl) -carbamoylpropyl} -carbamoylethyl -2-deoxy-C-gln) goat, 2-acetamino-3-0-O-1-b- {Dl -carbclmoyl-3-carboxypropyl) -carbamoyl-2. -oxy propyl arbamoylethyl-2-deoxy-B-glucose, 2-acetomino-3-0- {o-1- (D-1-carbamoyl-3-carboxypropyl) -carbamoyl-2 - (p-oxyphenyl) - etite -carbamoylethyl -2-deoxy-p-glucose 2-acetamino-3-0- (O-1-jI, -l- (Dl-Kap-, ba yuyl-3-carboxypropyl) carbamoyl - -H, L-tetramethylene -carbamoyl ethyl -, -2-deoxy-B-glucose 2-glycolylamino-3-0- {o-1-b-1- {0-1-carbamoyl | -3-carboxypropyl) -carbamoyl-methyl-carbamoyl ethyl -2-deoxy- B-glucota, 2-glycolylamino-3-0-1, 1- - (D-1-carbamryl-3-carboxypropyl) -carbg1-myoethyl 3 -carbamoylmethyl) -2-deoxy-B-glucose, 2- (N-methylacetamino) -3 -0- {; Ь-1- (о-1-carbamoyl-3-carbo Cipropyl) -carbamoyl ethyl-carbamoylmethyl -2-deoxy-B-GLYXOZ, 2- {N-methylacetamines -3-0-and-1 - {L I- (Dl-carbamoyl-3-carboxypropyl) -carbamoylethyl-rbamoylethy - 2-deoxy-1) -glucose, 2-acetamino-3-0-o-1-Cb-1- (O-1-carbamoyl-3-carboxyprypyl) -carbamoyl-2-phenyl ethyl-carbamoylztil-2-deoxy- D-glucose, 2-acetamino-3-0-L-1-- (D-1-carbamoyl-3-carboxypropyl) -carbamoyl-2 - (p-hydroxyphenyl) -ethich 1 "L zilcarboxypropylK arb c1Moylmetsh1 J.-2 - deoxy - and - glucose, 2-acetamino-Z-O- f L-1- (Dr-1,3-dicarboxypropyl-M- "gtilkarbg №yuylethyl-carbamoylmethyl -2-deoxy-0-glucose. Example 34. By analogy with the method described in example 19, an influenza virus antigen of the following type is obtained: A (Victory). 3/75 associated with 2-acetamino-3-O-fL- (Dl-carbox-3-carbox-propyl) -kapbamoilmetil -N-metilkapbamoilmetil -2-deoxy-D-glucose, 2-benzoylamino-W-O- {C (n-1-carbamoyl-3-carboxypropyl) -N-methylcarbamoylmethyl carbamoylmethyl -2-deoxy-D-glucose , 2-acetamino-3-0-Ll- (Dl-kap5amoyl-3-carboxopropyl) -carbamoyl ethyl -N-ethylcarbamoylmethyl -2-deoxy-T) -glucose, 2-acetamino-3-0-b-1- (D -1-carbamoyl-3-carboxypropyl) -carbamoylpropyl} -N-methylcarbamoylmethyl; -2-deoxy-C-glucose, 2-acetamino-3-0- {b-l- (Dl carbamoyl-3-carboxoxipropyl) -carbamoylprogl-Y-ethylcarbamoylmethyl -2-deoxy-glucose, 2-benzamido-3- O-1- - (D-1-carbamoyl-3-carboxypropyl) -carbamoyl-propi-N-ethylcarbamoylmethyl) -2-deoxy-C-glucose, 2-acetamino-3-0- {L-1- {D- 1-carbamo-3-carboxypropyl) -carbamoylethyl N-propylcarbamoylmethyl | -2-deoxy-T5-glucose, 2-aueTaMHHO-3-0-tL-1- (O-1-carbamoyl-3-carboxypropyl) -carbamoyl-N, N-Pentamethylene -carbamoylmethylj-2-deoxy-B - glucose, 2-bbnzoylamino-3-0- {CL-I- (D-1-carbamoyl-3-carboxypropyl) -carbamoyl-N, N-pentamethylene -carbamoylmeti-2-deoxy-TZ-glucose, 2-.acetamino -3-0- f L-1- (D- 1-carbamoyl-3-carboxypropyl) -N-methy carbamoylethyl l-carbamoyl and lmety l) -2 - de z-ok-T) -glucose, 2-acetamino -3-0- {o-1- (p-. J-1-carbamoyl L-3-carboxypropyl) -carvamoylmethylT-and-methi caroamoylethyl -2-deoxy-) -glucose, 2-benzoic amino-3-0- {O-lt (Dl-carbamoyl-3-carboxypropyl) -carbamoylmethyl -N -mear carbamoylethyl -2-deoxy-B-glucose, 2-acetamino-3-0-o-1-LI- (B-1-carbamoyl-3-carboxypropyl) -carbamoylethyl} -N-ethylcarbeurovuyletssh {1-2-deoxy -1) -glucose, 2-acetamino-3-0-0-1-1-1-l- (D-β-carbamo-3-carbox x-propyl) -carboamoylpropyl 7 yN-methylcarbamoylethyl 5 -2-deoxy, -D-glucose, 2-acetoxy-2-deoxy-, -D-glucose, 2-acetylcarbamoylethyl 5 -2-deoxy, -D-glucose, 2-acetoxy-2-deoxy-2 -3-0- {o-1-p / -1- (0-1-carbamoyl-3-carboxypropi: l) -carbamoylpropyl -M-ethylcarbamoylmethyl -2-deo.xy-1: glucose, 2-benzamn: to -, - 1- (0-1-carbamoyl-3-carboxypropyl) -carbamoylpropyl-M-ethylcarbamoylethyl) -2-deoxy-D-glucose, 2-acetamine-3-0-o-1-b-1- (0-1-carbamoyl-3-carboxypropyl) -carbamoylethylZ-N-p ropilcarbamoylethyl -2-deoxy-B-glucose, 2-acetamino-3-0-o-1-b-1- (0-1-car bamoyl-3-carboxypropyl) -carbamoyl-I / K-pentamethylene-carbamoyl ethyl -2 -deoxy-O-glucose, 2-benzoylamino-3-0-0-1-Cb-1- (0-1-kirbamoyl-3-carboxypropyl) -carbamoyl-S, N-pentamethylene -carbaMoylethyl3-2-deoxy- D-glucose, 2-acetamino-3-O-D-1-JL-1 - (O-1-carbamoyl-3-carboxypropyl) -M-methylcarbamoyl ethyl 3; -carbamoylethyl 5 2-deoxy-1) -glucose, 2-acetamino -3-0 Cb-1- (B-1-carbamoyl-3-carboxymethylphenyl} -carbamoylmethyl -2-deoxy-1) -glucose, 2-benzoylamino-3-Of (D l-carbamoyl-3-carboxymethylphenyl-carbamoyl-methyl -2-deoxy-B-glucose, 2-benzamino-3-0- (D-1-carbamoyl-3-carboxymethylphenyl-3-carbamoylmethyl -2-deoxy-0-glucose, 2-benzamino-3-O-L-1 - {D 1-carbamoyl-3-carboxy-propyl) -carbamoyl-2-methylmercapto-ethyl -carbamoylmethyl -2-deoxy-1) -glucose 2-benzamine-3-O-fL-1- {D-1-carbamoyl-3- car6oxypropyl) -carbamoyl-2-chloroethyl-carbamoylmethyl-2-deoxy-1) -glucose, 2-ace. amino-3-0-O-1-1-1- {0-1-carbamoyl-3, 3-dicarboxypropyl ) -carbamoyl ethyl -carbamoylethyl -2-deoxy-1) -glucose, 2- (beta-carbomethoxy succinamido) -3-0-f L-1- (B-1-carbamoyl 3-carboxypropyl) -carbamoylethyl-3-carbamo Methyl-2-deoxy-1) -glucose, 2 {beta-carbomethoxysuccinamido) -3-0-b-1-b-1- (Dl-carbamoyl-3-carboxim-propyl) -carbamoylethyl-3-carbamoyl ethyl | -2-deoxy-T ) -glucose, 2-benzamino-3-0-1- (O-1-car6amoyl-3 trimethylsilylcarboxyprrpyl) -carbamoyl ethyl -carbamoylmethyl -2-deoxy-4, b-tris-trimethylsilyl-b-glucose ( in contact with water, the trimethylsilyl ester groups are rapidly: washed), 2-acetamino-2-deoxy-3-0-tL-l- (Di-carbamoyl-3-trimethylsilylcarboxypropyl) -carbamoylethyl-carbamoylmethyl-1, 4,6-tris -trmmethylsilyl-B-glucose, 2-acetamino-3-0-o-1-l-1- {0-1-carbamoyl -3-carboxypropyl) -carbamoyl. Propyl-carbamoyl ethyl -2-deoxy-B-glucose, 2-acetamino-3-O-fo-1-b-1- (0-1-carbamoyl-3-carboxypropyl) -carbamoyl- 2-hydroxypropyl-carbamoylethyl -2-deoxy-1) -glucose, 2-acetates O-3-0-p-1-1-1- (O-1-carbamoyl-3-carboxypropyl) -carbamoyl-2-- ( p-hydroxyphenyl) -ethyl-carbamoyl ethyl-2-deoxy-T1-glucose, 2-acetamino-3-0-1o-1-h-1- (0-1-carbamoyl-3-carboxybropyl) -carbamoyl-N, N trivoluene-carbamoyl ethyl -2-deoxy-1) glucose, 2-glycolylamino-3-0-o-1-h-1- (0-1-carbamoyl-3-carboxypropyl) -carbamoylethyl-carbamoyl ethyl -2-deoxy-B - glucose, 2-glycolyl no-3-Of b-1- (P-1-carbamoyl-3-carboxypropyl) -carbamoyl ethyl-3-carbamoylmethyl -2-deoxy-T) -glucose, 2- (N-methylacetamino) -3-0- tL-l- (Dl-carbamoyl-3-carboxypropyl) -carbamoyl ethyl -carbamoylmethyl | -2-deoxy-D-glucose, 2- (N-methylCetamino) 3-of (D-1-carbamoyl-3-carboxypropyl) -carbamoyl ethyl-carbamoyl ethyl -2 -dec-B-glucose, 2-acetamio-3-0-o-1-1-1- (0-1-carbamoyl-3-carboxypropyl) -carbamoyl-2-phenylethyl-carbamoylethyl-2-deoxy-G-glucose , 2-acetamino-3-0- ((L-1- (P-1-carbamoyl-3-carboxypropyl) -carbamoyl-2- (p-hydroxyphenyl) -ethyl-carbamoylmethyl -2-deoxy-T; -glucose, 2-a cetamino-3-0-tL-1- (O 1- / L-1-carboxyethyl / -carbamoyl-3-benzylcarboxypropyl) -carbamoyl ethyl-carbamoylmethyl -2-deoxy-1) -glucoeoy, 2-acetamino-3-0- | L-1- (D-1,3-dicarboxypropyl) -N-methyl. Carbamoyle: tyl-carbamoylmethyl -2-deoxy-B-glucose.
Example 35. By analogy with the method described in Example 121, anti-columnar serum bound to 2-acetamino-3-0- | - (EHl-carbamoyl-3-carboxypropyl) -carbamoylmethyl-methylcarbamoylmethyl -2-deoxy-T) -glucose, 2-benzoylyamio-3-0- | C (D-1-carbamoyl-3-carboxypropyl) -carbamoylmethyl -N-methylcarbamoylmethyl} -2-deoxy-F-glucose, 2-g-acetamino-3-0- (L7-1- (0-1-carbamoyl- 3-carboxypropyl) -carbamoylethyl-Y-ethylcarbamoylmethyl -2-dees1Xi-B-glucose, 2-acetamino-3-0-Hb-1- (D-1-carbamoyl-3-carboxylpropyl) -carbamoyl propyl -N-methylcarbamoylmethyl - 2-deoxy-B-glc goat, 2-acetamino-3-O-CL-1- (D-1-carbamoyl-3-carboxypropyl) -carbamoylpropyl-N-ethyl carbamoyl-methyl-2-fleaoKcH-B-glucose, 2 lido-3-0-G ((D-1-carbamoyl-3-carboxypropyl) -carbamoylpropyl -Y-ethylcarvamoylmethyl -2-dveoxy-T) -glucose 2-acvta foreign 3-0- (1.-1- {O-1-carbamoyl-3-carboxypropyl) -carbamoylethyl-It-propylcarbamoylmethyl 3 -2-deoxy-T} -glucose, 2-acetamino-3-0-C-1 - (O-1-car-6amoyl-3-carboxypdyl) -carbamoyl-N, N-pentamethylene -carbamoylmethyl 5-2-deoxy-1) -glucose, 2-benoylamino-3-0-Ll- {Dl-Kap6ai moyl-3 -carbopropyl) -carbamoyl-S, N-pentamethylene -carbamoylmethyl -; -2-deoxy-B-g. Püktozoi, 2-acetamina-. -3-0-GS1,1 (C-1-carbamoyl-3-carboxypropyl -Y-methylcarbamoyl ethyl-3-carbamoyl, methyl-2-deoxy-1) -glucose, 2-acetamio-3-0-0-1- (( C-1-carbamoyl-3-carboxypropyl) -carbamoylmethyl-N-methylcarbamoylethyl-2-deoxy-O-glucose, 2-benzoylamino-3-0- (o-1- (O-1-carbamoyl-3-carboxypropyl) - carbamoylmethyl-N-methylcarbamoyl-U ethyl -2-deoxy-1) -glucose, 2-acetamiumS) -3-0-To-1-1-1- (B-1-carbamoyl-3-carboxypropyl) -carbamoyl ethyl -ethylcarbamoyl ethyl -2-deoxy-b-glucose, 2-acetamino-3-0- {o-1-b-1 15 - (D-1-carbamoyl-3-carboxypropyl) -carbamoylpropyl -N-methylcarbamoyl ethyl 1-2-deso "Si-13-glucose 2-acetamino-3-0-P-1-L-1- (Dl-carbamoyl-3-carbox-propyl) -carbamoylpropyl} - 20 -Y-ethylcarbamoylmethyl -2-deoxy-T) -glucose, 2-benzamido-3- About D-1- (B-1-carbamoyl-3-carboxypropyl) -carbamoylpropyl 1-Y-ethylcarbamoyl ethyl -2-deoxy-O-glucose, 2- - y-acetamino-3-0-b-1-Gb-1- (0-1-carbamoyl-3-carboxypropyl) -carbamoylethyl -Y-propylcarbamoylethyl-2-deoxy-B-glucose, 2-acetamino-3-p-D-1-L-1- (D-1-carbamoyl-3 -carboxypropyl) -carbamoyl-S, L-pentamethylene-7-carbamoylethyl -2-deoxy-1-glucose, 2-benzoyllamino-3-0-0-1-1-L-1-
- (D-1-carbamoyl-3-carboxypropyl) -carbamoyls, L-pentamethylene -carbamoylethyl -2-deoxy-T) -glucose, 2-35 -acetamino-3-0-0-1-1-1 - (0-1-carbamoyl-3-carboxypropyl) -N-methylcarbamoylethyl -carbamoylethyl -2-deoxy-B-glucose, 2-acetamMo-3-0-b-1- (O-1-carbs1-mylo-3-carboxymethylphe- 40 Nile) -car6amoylmethyl -2-deoxy-TZ-glucose, 2-benzoylamino-3-0-1 {L-1- (D-1-carbamoyl-3-carboxymethylphenyl-carbamoylmethyl -2-desoxy.si-0-glucose, 2-Benzamino-3-0- {L-1- 45 - (D-1-carbamoyl-3-carboxypropyl) -carbamoyl-2-methylmercaptoethyl7-carbamoylmethyl -2-deoxy-B-glucoeo, 2-benzamino-3-0 - {tL al- (Dl-kap bamo Il-3-carboxamide) -carbamoyl. -2-chloroethyl-carbamoylmethyl -2-deoxy-B-glucose, 2-acetamino-Z-O | D-1-CL-1- (.U-1-carbamoyl-3 , 3-dicarboxypropyl) -carbamoylethyl -carbamoylethyl -2-deoxy-1) - lucosis, 2- (beta-
tkarbomethoxysuccinamido) -Z-0-f fL-1- (Dl-carbamoyl-3-carboxipropyl) -carbamoyl ethyl -carbamoylmethyl -2deoxy-1) -glucose, 2- (beta-carbonethoxysuccinamido-3-a-3) -glucose, 2- (beta-carboxethoxysucinimo-3-a-3 -one-
(D-1-carbamoyl-3-carboxypropyl) - 60 carbamoyl methyl-carbamoyl ethyl -2-deoxy-B-glumcose, 2-benzamido-3-0-Gb-1- (0-1-carbamoyl-3-trimethylsl-Mlcarboxypropyl) - carbamoylethyl} -carbs # 1oylmethyl -2-deoxy-1,4, b- 5
-tris-trimethylsilyl-O-glucose Schrn, in contact with water, trimethylsilicone esters grylps are quickly washed), 2-acetamino-2-lezoxy-3TO-LI- (D-1-carbamoyl-3-tri-Msylsarboxypropyl) -carbamboyl-3-carbamoyl-3-tri-m-lsilylcarbokspropyl-brabammoyl-3-tri-mbclymylcarboxypropyl-brabamboyl-3-carbamoyl-3-trimmicylsarboxypropyl-carbamboyl-3-trimethylsamide-3-trimethyl-3-trimethylsilyl; jl, 4,6-trisgtrimethylsilyl-I-glucose, 2-acetamino-3-0- ((Dl-carbamate-3-carboxylpropyl) -carbamoylpropyl-carbamoylethyl -2-deoxy-T} -glucose, 2-acetamino-3 O-DI-L-1- (B-1-carbamoyl-3-carboxypropyl) -carbamoyl-2-hydroxypropyl-carbamoyl ethyl -2-deoxy-1) -glucose, 2-acetamino-3-0-Cp-1- ( Dl-carbamoyl-3-carboxamide-propyl) -carbamoyl-2 - (p-hydroxyphenyl) -ethylZ-carbamoyl ethyl -2-deoxy-1) -glucose, 2-acetamino-3-0- {p-1-Ll- (Dl-carbamate-3-carboxo-propyl) -carbamoyl-N, N-tetramethylene 2-carbamoethyl -2-deoxy- 1) -glucose 2-glycolylamino-3-0, (Dl-carbamoyl-3-carboxo-propyl) -carbamoyl ethyl -carbamoylethyl -2-deoxy-B-glucose, 2-glycolylamino-3-O-fL-1-d-3-dl-glucose, 2-glycolylamino-3-glycolylamino-ethyl-3-deoxy-B-glucose, 2-glycolylamino-3-glycolylamino-ethyl -3-carbocipipropyl) -carbamoylethyl -carbamoylmethyl -2-deoxy-1) -glucose, 2- (N-methylacetamino) -3-0-tli-1- (D-1-carbamoyl-3-carboxypropyl) -carbamoylmethyl | -2-deoxy-1) -glucose, 2- (N-methylacetamino) -3-0-Dl-L-1- (D-1-carbamoyl-3-carboxypropyl) -carbamoylethyl-carbamoylethyl -2-deoxy-B- glucose, 2-acetamino-3-0-1-fD-1-L- (D-1-carbamoyl-3-carboxypropyl) -carbamoyl2-phenylethyl-carbamoylethyl -2-deoxy-O-glucose, 2-acetamino-3- Of Ll- (Dl-carbamate-3-carboxypropyl) -carbamoyl-2 - (p-hydroxyphenyl) -ethyl-carbamoylmethyl -2-deoxy-B-glucose, 2-acetamino-3-O- {CL-1- (D -1 / L-1-carboxyethyl / -carbamoyl-3-benzylcarboxypropyl) -carbamoyl ethyl -carbamoylmethyl) -2-deoxy-D-glucose, 2-acetamino-3-0-11, -1- (D-1,3- dicarboxypropyl) -N-methylcarbamoile Tyl -carbamoylmethyl -2-deoxy-TZ-glucose.
Example 36. By analogy with the method described in example 23, an anti-cholera serum from VibriochoEerae is obtained, which is bound to 2-acetamino-3-0-t (Dl carbamoyl-3-carboxypropyl) -carbamoylmethyl -H-methylcarbamoylmethyl-2 -H -D-glucose, 2-benzoylamino-3-O-C (0-1-carbamoyl-3-carboxypropyl) -carbamoylmethyl -Y-methylcarbamoylmethyl) -2-deoxy-B-glucose, 2-acetaminb-3- 0-LI- (DI-carbamoyl-3-carboxypropyl) -carbamoylethyl-N-ethylcarbamoylmethyl -2-deoxy-B-glucose, 2-acetamino-3-0-L-1- (D-1-carvamoyl-3-carboxypropyl ) -carbamoylpropyl 3-N-methylcarbamoyl ethyl 2-desoxy-T) -gluck ozoy, 2-acetone | amins5 3-0-L-1- {p-1-carbamoyl-3 -carboxypropyl) -carbamoylpropyl -N-ethylcarbamoylmethyl-3-deoxy-E-glucose, 2-benzamido-3-0- | - (D-1-carbamoyl-3-carboxypropyl) -carbamoylpropyl-N-ethylcharbamoylmethyl 2-deoxy-1) -glucose, 2-acetomino-3-0-Cb-1 (Dl-carbamoyl-3-carboxycyl) - carbamoylethyl-N-propylcarbamoylmethyl 1 -2-deoxy-0-glucoe, 2-acetates; but-3-0- | L-1- (D-1-carbamoyl-3-carboxypropyl) -carbamoyl-S, L-pentamethyl-Vn-carbamoylmethyl | -2-deoxy-1) -glucose, 2-benzoylamino-3-0- (P-1-carbamoyl -3-carboxypropyl) -carbamoyl-S, H-pentamethylene} -carbamoylmethyl} -2-deoxy-T} -glucose, 2-acetamio-3-0-Cb-1- (P-1-carbamoyl-3-carboxy: cypropyl) -Y-methylcarbamoylstil -. -carbamoylmethyl 1-2-deocdio-0-glucose, 2-acetamino-3-0- and-1-. (B-1-carb 3-carbrxypropyl; -carbamoylmethyl-M-methylcarbamoylethyl -2-deoox-D-glucose, 2 -benzoylamino-3-0- | p-1 -Gi-1-carbamoyl-3-carboxypropyl-ka bamoylmetesh1) -H-methylcarbamoyl ethyl -2 -deoxy-5-glucose, 2-acetamino-3-0- ((P -1-carbamoyl-3-carboxypropyl) -carbamoyl ethyl-N-ethylcarbamoyl ethyl -2-deoxy-1) -glucose, 2-acetamino-3-O-o-1-1-1- (0-1-carbamoyl-3- carboxypropyl) -carbamoylpropyl) N-methylcarbamoylethyl / -2-deoxy-1) -glucose, 2-acetamio-3-0-0-1-1-1-SP-1-carbamoyl-3-carboxypropyl) -carbamoylpropyl -Y- ethyl carbamoylmethyl -2-deoxy-Op-glucose, 2-benzaMido-3-o-1-b-1- (D-1-carbamoyl-3-carboxypropyl) -carbamoylpropyl-N-ethylcarbamoyl ethyl -2-deoxy-0-glucose 2 -acetamino-3-0-o-1-Gb-1- {O-1-carbamoyl-3-carboxyprpryl) -carbamoylethyl -Y-propylcarbamoylethyl -2-lezoxy-f-glucose, 2-acetamino-3-0- 0 -1-fL-l- (Dl-carbamoyl-3-carboxypropyl) -carbamoyl-S, N-pentamethylene -carbamoylethyl} -2-deoxy-T-glucose, 2-benzoylamino-3-0-0-1-fb- 1- - (D-1-carbamoyl-3-carboxypropyl) -carbamoyl-S, M-pentamethylene -carbamoylethyl -2-deoxy-0-glucose, 2-acetamino-3-0- {(B-1-carbamoyl-3 -carboxypropyl) -N- methylcar bamoyl ethyl -carbamoylethyl -2-deoxy-I-glucose, 2-acetamino-3-0-Cb - (D-1-carboxymethylphenyl 3 -carbamoyl methyl-3-deoxy-B-glucose, 2-benz ilamino-3-Of L -1- (D-1-carbamoyl-3-carboxymethylphenyl5-carbamoylmethyl-J-2-desokokvi-t) -glucose 2-benzaminog3-0-1-1-, (0-1-carbamoyl-3-carboxypropyl) -carbamoyl-2 -methylmercaptoethyl -carbamoylmethyl -2-deoxy-B-glucoEoy, 2-benzamino-3, (O-1-carbamoyl-3-carboxy; propyl) -carbamoyl-2-chloroethyl1-carba moylmethyl J -2-deoxy-P-glucose , 2-acetamino-3-0- {o-1-l-3- (O-1-carbamoyl-373gdicaroxypropyl) -carbamoylethyl-carbamoylethyl -2-dez i-B-glucose, 2- (beta-carbomethoxy-succinamido) -3-0-L-1 - (0-1-carbgs 1Oyl-3-carboxypropyl) -carbamoylethyl-carbamoylmethyl -2-deoxy-B-glucose, 2 - (beta-carbomethoxysuccinam- to) -3-0-O-1-l-1- (0-1-carbamoyl-3-carboxypropyl) -carbamoyl ethyl-carbamoyl ethyl -2-deoxy-T-glucose, -2-benzamic acid Z-O-G (D-1-carba-moyl-3-trimethylsilylcarboxypropyl) -carbamoyl ethyl -carbamoylmethyl -2-deoxy-1, 4, b-tris-trimethylsyl-T) glucose (upon contact with water, trimethylsilyl ester groups quickly olvllus), 2-acetamino-2-deoxy-3-0- | FL-1- (Dl-carbamoyl-3-trimethylsilylcarbocipropyl) -carbamoylethyl 3 -carbamoylmethyl -1, 4, b-tris-trimethylsilyl-D-glucose, 2-acetamino-3-0-o-1-l-1- -1-carbamoyl-Z. -K arbox ipropyl) -k arbamoyl propyl -carbamoylethyl -2-deoxy-T) -glucose, 2-acetamino-3-0- (o-1- | b-1- (0-1 -carbamoyl-3-Carboxypropyl) -carbamoyl-2 -oxypropyl -carbamoylethyl-2-deoxy-T) -glucose, 2-acetamino-3-0- {o-1-1-1- (Dl-carbamoyl-3-carboxylate) ) -carbamoyl-2 - (p-hydroxyphenyl) -ethylJ-carbamoylethyl -2-deoxy-D-GLUCOSE, 2-acetamino-3-0-O-1- --1- (O-1-carbamoyl-3 -carboxypropyl) -carbamoyl-S, N-tetramethylene -carbamoylethyl | -2- esoxy-1) -glucose 2-glycolylamino-3-0-o-1-L-1- (D-1-carbamoyl-3-carboxypropyl) -carbamoyl ethyl 3-carbamoylethyl -2-deoxy-P-glucose, 2-glycolylamino- H-O- | L-1- (Dl-carbamoyl-3-carboxypropyl) -carbamoylethyl-carbs1-moylmethyl -2-deoxy-1) -glucose, 2- (N-methylacetamino) -3-0-b-1- (Dl-cap6a-amoyl-3- carboxypropyl) -carbamoylethylT-carbamoylmethyl} -2-deoxy-T) -glucoic, 2- (K-methyl acetateMino) -3-0-o-1- 1- (D-1 - carb amoyl-3 - carboxypropyl) -carbamoyl ethyl D - carbamoylethyl -2-deoxy-0-glucose, 2-acetaminex) -3-0-O-1-b-1-- (O-1-carbamoyl-3-carboxypropylcarbamoyl-2-phenylethyl-carbamoylethyl} -2-deoxy- P-glucose, 2-acetamino-3-0-L-l- (Dl-carbamoyl-3-carbox-propyl) -carbamoyl-2 - (p-xyphenyl) -ethyl-carbamoylmethyl -2-deoxy-0-glucose, 2- acetamino-3-of l -l- (DI- / Ll-Kap6oKCH ethyl / -carbamoyl-3-benzylcarboxIpropyl) -carbamoyl ethyl -carbamoylmethyl. -2-deoxy-1) -glucose, 2-acetamino-3-0-L-1- (G) - 1g 3-dicarboxypropyl) -methylcarboxyethyl-carbamoylmethyl -2-deoxy-1) -glucosy. Example 37. By analogy with the method described in the example synthetic eicosapeptide.
which is identical to the human C-terminal sequence of human choriogonadotropin, linked to 2, -acetamino-Z-0-G (D-1-carbamoyl-3-carboxypropyl) -carbgi yulmetnl-N-methylcarbamO ylmethyl -2-deoxy-1) -glucose , 2-benzoylamino-3-0- (O-1-carbamoyl-1 -Z-carboxypropyl) -carbamoylmethyl t —Y methylcarbamoylmethyl -2-deoxy-; -D-glucose, 2-acetamino-Z-O-L-1- - (D-1-carbamoyl-Z-carboxypropyl) -, -carbamoylethyl-N-ethylcarbamoylJetn-2-deoxy-B-glucose, 2-acetamine 3-0- ((O-1-carbamoyl-3-carboxypropyl) -carbamoylpropyl-Y-methylcarbamoylmethyl -2-deoxy-0-glucozoy. 2-acetamine-3-OH-lL-l -; (Dl-kap bamoyl-3-carboxypropyl) -carbamrylpropyl -Y-ethylcarbamoylmethyl -2-deoxy-and-glucose, 2-6enzene and ido-3-0G b-1- (O-1-carbamoyl-3-carboxypropyl) -carbamoylpropyl) -Y- Ethylcarbum K n iuV rv "-rii.A -xyii" -xt / nx2 | hr jeu tx n "% 7 l.
-Y-propylcarbamoylmethyl -2-deoxy-D-glucose, 2-acetate1NO-.3-0- {L-1- - (0-1-carbamoyl-3-carboxypropyl) -. -carbamoyl-M, N-pentamethylene -carbamoylmethyl -2-deoxy-B-glucose, 2-benzoylamino-3-Of L-1- {Dl-Kap6dmoyl-3-carboxypropyl) -carbamoyl. -N N-pentamethylene-carbamoylmethyl 2 - deoxy - - glucose, 2 -: - aceteto # "nno-3-0-L-1- (0-1-carba-yuyl-3-carboxypropyl) -Y-methylcarbamoyl ethyl} -carbamoyl (1-methyl -2-deoxy-T) - glucose,
2-Acetamino-3-0- {o-1-t {Dl-cdrbamo M-3-carboxopropyl) -carbamoylmethyl-J-y-methylcarbamoylethyl1-2-deoxy-D-glucose, 2-benzoylamine-3-0 o-1- (O -1-carbamoyl-3-carboxypropyl) -carbamoylmethyl -N-methylcarbamoyl ethyl -2-deoxy-amp-glucoe, 2-acvtamino-3-L- 0-1-b- 1- (O-1-carbamoyl-3 -carboxypropyl) -carbamoylethyl -N-ethnlcarbamoylethyl -2-deoxy-1); - glucoare, 2-acetam1tr-3-0- {p-1-L-1- (D-1-carbamoyl-3-carbxypropyl) -carbam6ylprrp "L1-M-metiltilkarvamoyletilI-2-deoksi-0-gl1okrzyr, 2-acetacnto-3-0- 0 1-tl -l- (Dl-Kap6amoyl-Z-carboxypropyl) -kaipusaeot / uaipo saw | -N- ethylcarbamylmethyl -2-dveHi-0-gluco; angry, 2-Benz "edr-3-0-Go-1-L-1- (D-1-carbamoyl-3-kgfbRKsIpropyl) -car bamoylproNyl1-N-ethylcarbamoylethyl) -2-desrxy-F-gl1bkreoy, 2-acetamide 3-0-1-Cb-1- (0-1-carbamoyl-3-carboxypropyl) -carbamrylethyl-N-propylcarbamRilethyl) -3-desirby-0-glucoeoy, 2-acetaminr-3-O- {o -1- L-1- {0-1-carbamryl-3-carbrccipropyl) -carbamoyl-S, N-pengamvtililna; | -carbamryl ethyl-2-de srxi-1) -glucose, 2-benzoylaminr-3-0- { o-1- li-
- (D-l-bamoyl-3-carbrkeiprrpil) -carbamo11l-N, N-pentamethylene -carba
Moylstil} -2-desRXi-β-glucRzoy, 2-acetamine-3-0-0-1-1; 1, -1- (0-1-carbamoyl-3-carboxypropyl) -N-methylcarbamoyl ethyl-3-carbamyl ethyl -2-deoxy -B-glucoser, 2-acetamine-3-0-1- (O-1-caobamoyl-3-carboxymethylphenyl in nyl -carbamrylmethyl | -2-desrksi-T - t -glucose pj, 2-ben 3 oylamino-3 -0-ffL-1 - (O-1-carbamoyl-3-carbRXMYPHYPE NILE-CARBAMOI; ETHYL-2-2-deoxy -) - glucry, 2-benzayino-3-0- {L-1- (D-1-carbamoyl -Z-carboxylpropyl) -carbamoyl-2-methylmercaptRZTyl -carbamrylmethyl) -2-desrxy-T) -glucrZRy, 2-benzaxnr-3-0-L-1- (0-1-carbamryl-3-carbrxyxylphenyl) -carbamoyl- 2-hlrretil-carbamoylmethyl | -2-dezok C-B-glucose, 2-acetamino-3-O- | o-1-l-1- {0-1-carbamoyl-3, 3-carbarxylphenyl) -carbamrnleethyl -carbamrylateethyl -2-des RKsi-1) -GLUKRRY, 2- (beta-carbrmethoxy-succinamido) -3-0- (D f Pbamoyl-3-carboxam pppyl) -carbamoyl ethyl -carbamoylmethyl -2-deoxy-P-glucryr, 2- (beta-carbrmetrxysuccinamidr) -3-p-D-1- {L-1-, - (0-1-carbamryl 3-carbrxyprrpyl-carbamyl ethyl 3-carbamryl ethyl-2-des-xy-) -c-GLUKRZRJ, 2-benzalshnr-3-O-C-1- (G) -1-carbamyr-3-trimethylsilylcarbr-xycrrpyl) -carbamryl-dl-al-3-tri-cyclryl-3-trimethylsilylcarbroxy-3-trimethylsilylcarbrxyphenyl-3-carbamyryl-3- -1, 4,6-tris-trimethylsilyl-B-glucose (when in contact with vrdoy trimethylsilyl slvnrefirnye groups bystrom were), 2-acetaminr-2-desrksi-3-0-LI- (, D-1-carbamRyl-3-trimethylsilylcarbrxylpropyl) -carbamrylethyl-carbamrylmeti-1, 4, b-tris-trimethylsilyl-C-glucrryryu-1 acetamino-3-O-D-1- | b-1- {1) -1g-carbamoyl-3-carbrxiprrpyl -carbamrylprprpilZ-carbamrilethyl -2-desrksi-B-gluc6zoi, 2-acetaminr-3-Og o-l- -fL l- 0-1-car6amril Z- .carbRxiprrpyl) -carbamryl-2-rxiprRpilZ -carbacgoylethyl -2-desrksi-1 -glyukrzry, 2-gschvtaminr-3-From {o-1-l-1- ( O-1-carbamryl-3-k) arbrxyprrpyl) -carbamryl-2 - (p-xyphenyl) -ethyl -carbamrylethyl) -2-desRXiCH) -glyukrzry, 2-acetaminyr-3-0- (o-1-G1, -1 - (O-1-carbamryl-3-cara | brksisch Rpyl) -carbam, Ryl-N, N-tetram ylen1-carbamrilethyl -2-desrksi-P-glucreRy., 2-glycrlylamino-3-0-o-1 1 -1- (O-1-carbamryl-3-carbrxiprrpyl) - carbgshRyylethylZ -carbamoylethyl} -2-desrksy- & glyukrzry, 2-glycrylamine R-3 0-1-1 -1 {O-1-carbamryl-3-car 5rxipipronil) | -carbamrylateethyl -carb-MRIlmetul1g2 -e-hydroxy-β-carbamrythyl ethyl -carbyl-MRIlmetul1g2-ae-hydroxy-3-carbamrylate ethyl -carbam-MRIlmetul1g2-ae-hydroxy-3-carbamrylate ethyl -carbamide-MRImmetul1g2-ae-hydroxy-3-carbamrylate ethyl -carbamylamine-3-xyroxyphenyl) -carbamrylate ethyl -carbamyl-3-carbamrylate ethyl-carbamyl-3-car 5 2-glycriamino-3-Of fL-1-CD-1-carbamoyl-3 to boxypropyl J-carbamoylethyl} -carba | "ylmethyl 2-desrksi-1) -glucose, 2- (N-me and 1 acetaminr-E-0 - {L-1- (D- 1-carvamryl-3-car6rksiprrpil) -carbamrylSTitnJ -carbamrylmethyl -2-desrksi-} -glucoea, 2- {H-methyl acetamine) -3-0- {Dl-JIb-1 - (( 1) -1-carba.mril-3-k arbrxypropyl) carbamoylethyl-carbamoyl ethyl -2-deoxy-B-glucose, 2-acetamino-3-0-o-1-1-1- (0-1-carbamoyl-3-carboxypropyl) -carbamoyl-2-phenylethyl-carbamoyl ethyl - 2-deoxy-TZ-glucose, 2-acetamino-3-0-G B-1 - - (D-1-carbamoyl-3-carboxypropyl) -carbamoyl-2 - (p-hydroxyphenyl) -ethyl) -carbamoylmethyl 5 -2 -deoxy-1) -glucose, 2-acetamyl-3-0- {L-1- (0-1- / L-1-carboxyethyl / -carbamoyl-3-ben zylcarboxypropyl) -carbamoylethyl-carbamoylmethyl | -2-deoxy- 1) -glycotic, 2-acetamino-3-0-1- {O-1,3 dicarboxypropyl) -N-methylcarbamoyl ethyl -carbamoylmethyl -2-deoxy-1) -glucose. These muramyl peptides and their derivatives combined with bridged fragments are new compounds. They can be obtained, for example, from analogs with the following example, Example 38. A solution of 3.4 g of benzyl 2-acetamino-3-0-O-1-1-1-o-1-carbamoyl-3- (benzyl ester) L-1-carboxylicethylcaiJabmoiJi) -propyl -carbamalethyl1-carbamoylethyl) G-2-deoxy-alpha-P-glucopyranoside in 100 ml of a mixture of methyl alcohol and distilled water 2/1 for 24 hours is hydrogenated at atmospheric pressure and temperature in the presence of 0 , 3 g of 10% palladium on carbon. Then the catalyst is separated from the reaction mixture by filtration and the filter is evaporated. The resulting residue is dissolved in 40 ml of water and the solution is extracted three times with saturated water - butyl butyl alcohol three times, using 40 ml of the latter each time. The organic phase is washed three more times with water, saturated with secondary butyl alcohol, using each time 40 ml of this water. The aqueous solutions are combined, evaporated, the residue is dissolved in a small amount of distilled water, and then freeze-dried. As a result, 2-acetamino-Z-O. -carbamoyl-E- (L-1-carboxyethylcarbamoyl) -propyl -car bamoylethyl -carbamoylethyl -2-deox-D-glucose is obtained in the form of a white powdery substance with (+9 ± (distilled water , s 1.090). The starting material used is obtained as follows. A solution of 6.1 g of benzyl -2-acetamino-3-0-1-b-1- (0-1-car bamoyl-3-carboxypropyl) monohydrate) carbamoylethyl-J-carbamate-2-deoxy-alfa-O-glucopyranoside and 3.5 g of p-toluenesulfonate L-alanine benzyl ester in 30 ml N, N-dimethylforma and mixed with 1.4 MP of triethylamine, G, 1 g N-oxysuccin Nimide and 2.3 g of dicyclohexycarbodiimide and the reaction mixture is stirred for 48 hours at room temperature.The cyclohexylurea precipitated out in crystalline form is filtered off, the precipitate is washed with 10 ml of S, H-dimethylformamide and the filtrate is evaporated to dryness. The residue is suspended in 100 ml of water, the suspension The mixture is stirred for 1 hour, the insoluble material is separated by filtration, washed with a small amount of water, cooled with ice, and then dried. The product is dissolved in methyl alcohol, precipitated by adding a double amount of ethyl acetate, filtered, washed with a small amount of ethyl acetate and dried, + 72 ± 1 (methyl alcohol, 0.998). When benzyl-2-acetamino-3-0- (Dl-carbamate-3-carbox JCIpropol-carbamoylethyl-carbamoyl mermij -2-deoxy-alpha-B-glucopyranoside-2-deoxy-alpha-B-glucopyranoside is used as the starting material, 2-acetamino-3-0- -1- {D-1-carbamoyl-3- (L-1-carboxyethylcarbamoyl) -propyl) -carbamoyl ethyl -carbamoylmethyl J-; -2-deoxy-0-glucose.j When using benzyl-3-0- {B-1-.L-1-carbamoyl-3-carboxypropyl-carbamoylethyl-carbamoylethyl-2-deoxy-2 as starting materials -propionamino-alpha-B-glucopyranoside and para-toluenesulphonate of glycine benzyl ester are obtained. -propionamino B-glucose. In a similar way, 2-acetamino-3-0-1 {L-1- (0-1-carbaguyl-3- (carboxymethylcarbamoyl) -propyl -carbamoyl ethyl -carbamoylmethyl -2-deoxy-D-glucose, 2-butyroylamino -3-0-0-1- {d-1- (b-1-carbamoyl-3- (l-1-carbxyxyethylcarbamoyl) -propyl -carbamoyl ethyl -carbamoylethyl -2-deoxy-o-g pokdzu, 2-butyroylamino- H-O-L-1- | (p-1-carbamoyl-3- (L-1-carboxyethylcarbamoyl) -propyl -carbamoyl ethyl -carbamoylmethyl -2-deoxy-O-glucbeu, 3-0-1-o- 1-carbamoyl-3- {carboxymethylcarbamoyl) -propyl -carbamoylethyl | -carbamoylmethyl g -2-deoxy-2-propionate and 0-glucose, 2-iso-butyroylamino-3 -0-1-1 -1-carbamoyl-3- (11g-1-carb; ethyl ethylcarbamoyl) -propyl -carbamoylpropyl -carbamoylmethyl1 -2-deoxy-0-glucose, 2-isobutyrylamino-3-0-Tv-1 - L-1- -carbamoyl-3- (L-1-carboxyethylcarbamoyl) -propyl -carbamoylpropyl -carbamoylmethyl1 -2-deoxy-P-gluco, 2-iso-butyrylamino-3-O-L-rl-fD-1- carbamoyl-3- (L-1-carboxyethylcarbamryl) -prrpyl -carbamoylpropyl -carbamoylethyl -2-deoxy-P-glucose, 2-iso-butyroylamino-Z-O-D-1-j L-1 - -carbamoyl-3- (L-1-carboxyethylcarba moyl) -propyl-carbamoyl-2-methylpropyl-carbamoylmethyl-1-2-deoxy-1) -gly goat, 2-iso-butyroylamino-3-0-1 l-1 - D-1-carbamo L-3- (karboksimetilkar bamil) -propyl j-carbamoylethyl -carbamoylmethyl (2-deoxy-D-glucose, 2-iso-C butiroilamino-3-0-1), - | D-1-carbamoyl-3- (carboxymethylcar, bamoyl) -propyl -carbamoylethylC-carj bamoylmethylT-2-deoxy-1) -glg.kzzu, 2-iso "butyroylamino-3-0-L lj D-1-carbamoyl- 3- (carboxymethylcarbamoyl propyl 3-carbamoyl ethyl carbamoyl ethyl-β-deoxy-0-glucose, 2-iso-butyroylamino-3-o-U L-1-Dl-Karbs 1 -moyl-3- (L-1-carboxyethylcarbamoyl) -be-carboxyethylcarbamoyl; -carbamoylmethylU-2-deoxy-O-glucose, 2-iso-butyroylamino-3-0-) P-1-1-1-o-1-carbamoyl-3- (L-1-to-arboxyethylcarba moyl -} - propyl-ka |) bamoylethyl-carbamoylethyl -2-deoxy-O-glucose, 3-iso-butyroylamino-3-O-b-1-c-1-carbamoyl-3-cj-l-carbox papilkap bamoyl) -propyl-carbamoyl ethyl) -carbamrylmethyl -2-deoxy-0-glucose, 2-acetamino-3-0-b-1- | o-1-carbamo-3) -carboxymethylcar) yamoyl) -propyl -carbamryl-2-methylpropyl -carbamoyl methyl -2-deoxy-o-glucose, 2-acetamino-3-0-Dl-fL-l-Dl-carbamoyl -3- {carboxymethylcarbamoyl) -propyl -carba 1oyl-2-methylpropyl -carbamoyl ethyl -2-deoxy-P-glucose, 2 acetamino-3-0-1 {y-1-o-1-carbamoyl-3- (L l-carboxyethylcarbamoyl) -propyl -carbamoyl-2-methylpropyl -carbamoyl methyl-2-deoxy-1) -glucose, 2-acetamino-3-O-Dl-BH, -1-o-1-carbamoyl-3- (L -1-carboxyethylcarbamoyl) -propyl -carbamoyl-2-methylpropyl -carba monleethyl -2-deoxy-T) -glucose, .2-acetamino-3-0-1, -1-O-1-carbamoyl -3- (L -1-carboxypropy carbamoyl) -propyl -carbamoyl-2-methylpropyl -carbamoylmethyl 1 l -2-deoxy-and-hl) Koza, 2-butyroylamino-3-0-1-o-1-carbamoyl-3- (L-1-carboxybutylcarbamoyl ) -propyl -carbamoyl ethyl -carbamoylmethyl 2-deoxy-0-gl okose, 2-acetamino-3-0-O-1- {l-1-D-1-carbamoyl-3- (L-1-ka 1boxyethylcarbamoyl-propyl -carbamoylpropyl -carbamoyl ethyl -2-deoxy-B-glucose, 2-acetamino-3-0-1 l-1-o-1-carbamoyl-3- (lt1-carboxyethylcaro-amoyl) -propyl-carbamoyl propyl-carbamoylmethyl-2- dvsoxy-V-glucose, 2-acetamine 6-3 -0-D-1-L-1-L-1-carbamoyl-3- {carboxymethylcarbamoyl) -propyl -carbamoylpropyl1 | -carbamo Il-2-leoxy-D-glucose, 2-acetamino-3-0-L-1-b-1-carbamoyl-3- {carboxymethylcarbamoyl) -propyl-carbamoylpropyl. -carbamoylmethyl -2-de-oxy-gl10KoZU, 2-acetamino-3-O-1-0-1-carbamoyl-3- {L-1-carboxypropylcarbamoyl) -propyl-carbamoylethyl-carbamoylmethyl-2-deoxy- 1) -glucose, 2-acetamine Z-0-B-1-L-1-o-1-carbamoyl-3- (L-1-carboxypropyl arbamryl) -propyl-carbamoylethyl-carbamoylethyl-2 g Deoxy-B-glucose, 2 - Acetamine o-3-O-gb-1-o-1-carbamoyl-3- (l-1-carboxy-2-methylpropylcarbamoyl) -propyl -carbamoyl ethyl -carbamoylmethyl-2-deoxy-D-glucose, 2-acetates; H-O-O-1- (1.-1-O-1-carbamoyl-3- {b-1-carboxy-2-methylpropylcarbamoyl) -propyl-1-carbamoylethyl-carbamoyl ethyl-2-deoxy-T1-gluk zu 2-acetamino-3-0- {s-1- | O-1-carbamoyl-3- (L-1-carboxybutylcarbamoyl) -propyl. -Carbamoylethyl-carbamoylmethyl -2-deoxy-O-glucose, 2-butyryloyl-; no-3-0-1 fL-l-D-l-carbamoyl-3- {car; boxymethylcarbamoyl) -propyl -carba-1 milylethyl -carbamoylmethyl1G-2-deoxy-D-glucose, 2-butyroylamino-3-O-0-1-y-1-0-1-carbamoyl-3-i -carboxypropylcarbamoyl) Propyl-carbamoyl-methyl-carbamoyl ethyl -2-deoxy-B-glucose, 2-butyroylamino-3-0-1-1-o-1-carbamoyl-3- {L-1-carboxypropylcarbamoyl) propyl-carbamoyl ethyl-carbamoylmethyl-2- deoxy-- .B-glucose, 2-butyroylamino-3-0-f Dl-Ll-fD- -carbamoyl-3- (L-1-carboxy-2-methylpropylcarbamoyl) -propyl -carbamoyl ethyl -carbamoyl ethyl T-2-deoxy- 1) -glucose, 2-butyroylamino-3-0-J L-1-D-1-carbamoyl-3- (L-1-carboxy-2-methylpropylcarbamoyl ) -Propyl gkarbamoiletil carbamoylmethyl -2-deoxy-T) -glucose, 2-benzoylamino-3-0- | L-1-o-1-carbamoyl-3- {L-1-carboxyethylcarbamoyl) -propyl -carbamoyl ethyl -carba-g myalmethyl -2-deoxy-B-glucose, 2-benzoylamino-3-0-O-1-ь -1- 1 -1-carbamoyl-3- {carboxymethylcarbamoyl) -propyl -carbamoylethyl -carbamoylethyl -2-deoxy-13-glucose, 2-benzoylamino-Z-O- | L-1-0-1-carbamoyl-3- {L-1-carboxyethylcarbamoyl) -propyl -carbamoylpropyl -carbamoylmethyl - -deoxy-B-glucose, 2-benzoylamino-3-0-O-1- {L-1 - o-1-carbamoyl-3- (carboxymethylcarbamoyl) -pryupil -carbamoylpropyl -carbamoyl ethyl -2-deoxy-T) -glucose, 2-acetamino-3-OV LI-D-1-carbamoyl-W- {L-1- carboxyethylcarbamoyl) -propyl -carbamoyl-N, N-tetramethyleneJ-carbamoylmethyl -2-deoxy-P-glucose, 2-acetamino-3-0- | about 1-L-1-o-1-carbamoyl-3- {L- 1-carboxyethylcarbamoyl) -propyl -carbamoyl-K, N-tetramethylene -carbamoylethyl -2-deoxy-glucose, 2-acetamino-3-Of L-1-p-1-carbamoyl-3- {carboxyme tilcarbamoyl) -propyl -. -carbamoyl-N, N-tetramethylene -carbamoylmethyl -2-desoxy-1), 2-acetamino-3-O-pl- {Ll-Dl-Kap6amoyl-3- (carboximethylcarbamoyl) -propyl-arbsh4oil-Y, Y -tetramethylene 5 -carbamoylethyl -2 deoxy-13-glucose, 2-acetamino-Z-O-L-1-D-1-carbamoyl 3- (L-1-carboxyethylcarbamoyl) -propyl-carbamoyl-2 hydroxyethyl-carbamoyl. methyl - 2-deoxy-U-glucoeu, 2-acetaminb-3-O-D l-Ll-tD-l-carbamate-3- (L-1-carboxyethylcarbamoyl) -propyl-carbamoyl-2-hydroxyethyl-carbamoyl ethyl 2-deoxy -1) -Glucose 2-benzoylamino-Z-O-1-o-1-carbamoyl-3- (L-1-carboxyethylcarbamoyl) -propyl-carbamoyl-2-hydroxyethyl-carbamoylme THJf f-2-desrxy-B-glucose, 2-benzoylamino 3-0- / O-1-L-1-o-1-carbamoyl-3- (L-1-carboxyethylcarbamoyl) -propyl-carbamoyl-2 hydroxyethyl-carbamoyl ethyl -2-deoxy-1) -glucose, 2 acetamino-3-0-y {l-1-b-1-carbamoyl-3- (L-1 carboxymethyl) -carbamoylpropyl-carbamoylmethyl-carbamoylmethyl -2-deoxy. -glucose, 2-acetamino-3-0-0-1-1-1-o-1-carbamoyl-3 {Ll-carboxymethylcarbamoyl) -propyl -carbamoylmethyl -carbamoylethyl -2-deoxy-B-glucose, 2-acetamine 3-0-b-1-0-D-carbamoyl-3- (L-1-carboxymethylcarbamoyl) -propyl -carbamoylmethyl -carbamoylmethyl} -2-deoxy-O-glucose, 2-acetamino-3-0- 0-1 - l-1-o-1-car amoyl-3- (L-1-carboxymethylcarbamoyl) -propyl -carbamoylmethyl -carbamoylethyl -2-deoxy-P-glucose - g 2-acetomino-3-O-f fir-1 - o-1-carbamoyl-3- (L -1 carboxymethylcarbamoyl) -propyl -carbamoyl methyl carbamoylmethyl -2-deoxy.-O-glucose.
Pr and m-e p 39. A solution of 4.2 g of benzyl-2-acetamino-3-0-Gb-1-D-1 - -carbamoyl - 3- (L-5-benzyloxycarbonylamino-5-carbamoylpentylcarbamoyl) - propyl} -carbamoylethyl -carbamoylmethyl -2-deoxy-alpha-P-glucopyranoside in 100 l of a 2/1 mixture of methyl alcohol and water is hydrogenated at atmospheric pressure and at room temperature in the presence of 0.5 g of 10% palladium on carbon. In this case, the pH of the reaction mixture is sub-elevated to level 6 by adding 1 and hydrochloric acid solution. After the hydrogen uptake is complete, the reaction mass is filtered off from the catalyst and the filtrate is evaporated to dryness. The residue is dissolved in a small amount of distilled water and freeze-dried. The result is 2-acetamine-3-0-L-1-1 -1-carbamoyl-3- (b-5-amino-5-carbamoylpentylcarbamoyl) -propyl-3-carbamoylethyl-carbamoylmethyl -2-deoxy-O-glucose hydrochloride in the form of a white powdery substance
: on.
Applied source material can be obtained as follows.
A solution of 15 g of methyl alpha-carbobenzoxy-E-tert-butoxycarbonyl-b-lysine in 100 ml of saturated methanolic ammonia is kept for 48 hours at room temperature and then evaporated to dryness. The resulting product alpha-carbobenzo-β-tert-butoxycarbonyl-L-lysinamide is recrystallized from a mixture of methyl alcohol and diethyl ether. M.p. product 142C, -3 + l (methyl alcohol, 1I018).
Chilled to a solution of 3 g. Alpha-carbobenzoxy-tert-butyloxocarbonyl-L-lysinamide in 25 ml of trifluoroacetic acid is stirred in
within 1 h and immediately thereafter evaporated to dryness. The residue is mixed with 20 ml of a saturated solution of sodium chloride and ice. By the addition of concentrated ammonia solution, the mixture is made alkaline, followed by extraction with ethyl ester of acetic acid. The organic phase is again washed with a saturated solution of sodium chloride, dried over sodium sulfate and evaporated to dryness. The result is alpha-carbobenzoxy-b-lysinamide in the form of a white foamy substance.
A solution of 5.6 g of benzylt-2-acetamino-3-0-l-1- (0-carbamoyl-3-carbox-; | cypropyl) -carbamoylethyl-carbamoylmethyl -2-deoxy-alpha-B-glucopyranoside and. 2, 8 g of alpha-carbobenzoxy-L-lysinamide and 30 ml, S, K-dimethylformamide are mixed with 1.1 g of N-oxysuccinimide and 2.2 g of dicyclohexylcarbodiimide and the reaction mixture is stirred for 40 g at room temperature, the precipitated the crystalline dicyclorexyl urea is filtered off and washed with 10 ml of S, M-dimethylformamide. The filtrate is evaporated to dryness and the residue is extracted with 100 ml of distilled water for 30 minutes. Nerasvorenny product was filtered, washed with water and dried to yield benzyl 2-acetamino-W-O- JL-1-fo-1- carbamoyl-3- (L-W-benzyloxycarbonylamino-5-carbamoylmethyl-karbamoilpentilkarbamoilpropil -karbamoiletilZ -2- deoxy-alpha-O-glucopyranoside. The product is recrystallized from a mixture of methyl alcohol and ethyl acetate.
In a similar way receive. 2-acetamino-3-O-fb-1-hydrochloride in 1-carbamoyl-3- (5-amino-L-1-carbamoylpentylcarbamoyl) -propyl - to ar bamoyl etyl-to arb amoyl meth t 2 -deoxy-O - gloxoses. Example 40. A solution of 2.8 g of benzyl-3-0-LI- (DI-carbamoyl-3-carboxypropyl) -carbamoylpropyl-carbamoylmethyl -2-deoxy-2-isobutyroylamino-alefa-B-glucopyranoside in 80 ml of a mixture of methyl alcohol and Waters 1/1 are hydrogenated at atmospheric pressure and a temperature of 45Pc in the presence of 0.3 g of 10% palladium on carbon. After treatment of the reaction mixture and freeze-drying the residue obtained Z-0-f | iL-l- (D-l- kapbamoil-3-kapbokcippopil) -kapbamoilppopil-kapbamoilmetil -2-deoxy-2-izobutiroilamino-B-glucose as a white powdered substance. The applied starting material is obtained according to the following procedure. A mixture of solutions of 21.0 g of benzyl-2-aminoNo-2-deoxy-4, 6-0-isopropylidene-alpha-B-glucopyranoside in 150 m of chloroform and 9.0 g of acidic potassium carbonate in 150 ml of distilled water is cooled with stirring mix and drop by drop with 8.5 ml of isobutyric acid chloride. After stirring the reaction mixture for 1 hour at room temperature, the organic phase is separated, washed with ice-cooled 0.5N. hydrochloric acid, water, a saturated solution of sodium hydrogen carbonate and again with water, dried and evaporated. The product benzyl-2-deoxy-2-isobutylamine-4, b-O-isopropylidene-alpha-B-glucopyranoside is recrystallized from 150 ml of diethyl ether. M.p. about product .VD +109 ± 1 ° (chloroform, from 1,017). A solution of 15.1 g of benzyl-2-deoxy-2-isobutyrylamino-4, 6-0-isopropyl-alpha-O-glucopyranoside in 150 m absolute, acetonitrile in nitrogen atmosphere under conditions that exclude the presence of moisture, and mixed with stirring With 1.9 g of sodium hydride and the reaction mixture is stirred for 1.5 hours at. Immediately after this, the reaction mixture is cooled before and mixed with 5.6 MP of methyl ester of bromoacetic acid. The mixture is stirred for another 15 minutes in an ice bath and for 2 hours at room temperature. After treatment of the reaction mixture, benzyl-2 deoxy-2-isobut. Alamino-4, b-O-isopropylidene-3-0-methoxycarbonylmethyl-alpha-B-glucopyrazide is obtained, which is recrystallized using an ethyl acetate mixture of diethyl ether and petroleum ether. So pl, product 119-120s (chloroform, from 0.963), a solution of 3.16 g of benzyl-2-deoxy-2-isobutyrylamino-4, b-0-isopropylidene-3-O-methoxycarbonylmethyl-alpha-Ogglucopyranoside in 30 ml meryl alcohol and 10 ml of 1 n. The sodium hydroxide solution is kept for 1 hour at room temperature. Then 3 ml of 1N hydrochloric acid is added to the solution and evaporated to dryness. The residue is dissolved in 50 ml, S, N-dimethylformamide, the solution is mixed with 2.26 g of L-alpha-aminobutyroyl-O-isoglutamine tert-butyl ester hydrochloride and 1.75 g of EEOa and the reaction mixture is kept at room temperature for 24 hours. Then, 0.2 g of EEDd is added to the mixture for another 24 hours, then the solvent is distilled off from the reaction mixture and the resulting residue is dissolved in a mixture of ethyl ester of acetic acid and water. The organic phase is separated, washed with cooled ice of 1N, hydrochloric acid solution, water, saturated sodium hydrogen carbonate solution, and again with water, dried over sodium sulfate and evaporated to dryness. The resulting benzyl tert-butyl ester is 3-0- (L-1I- (D-1-to arbamoyl-3-carboxypropyl) -carbamoylpropyl-3-carbamoylmethyl -2-deoxy-2-isobutylamino-4, 6-0-isopropylidene-alpha-B-glucopyranoside as a white foamy substance. Received the product is dissolved in 60 ml of glacial acetic acid, the solution is mixed with stirring with 60 w and the mixture is kept for 24 hours at room temperature. Then: the solution is evaporated to dryness in a vacuum; water jet, the precipitate is dissolved in ethyl alcohol. The solution is filtered with activated carbon and the filtrate is again evaporated to dryness to give benzyl tert-butyl ether . (Dl-carbamoyl-3-carboxamide) -carbamoylpropyl -carbamoylmethyl -2-deoxy-2-isobutyroyl amine-alpha-o-glucoproxyranoside as a white amorphous substance CO (+74 + l (methyl alcohol, with 0.950). A solution of 3.9 of the obtained tert-butyl ether in 40 ml of 98% trifluoroacetic acid, cooled to os, is stirred for 1 h at. and then poured into 500 ml of absolute diethyl ether. The precipitated crystalline product is filtered off, washed with diethyl ether and dried in vacuo. The obtained powdery substance is dissolved in 40 ml of water and tetrahydrofuran for 1/1 and for 30 minutes they are made by alternation with 5Q ml of Dowex 3 ion-exchange resin (in the acetate form). The ion exchange resin is filtered and washed with 500 ml of a mixture of tetrahydrofuran and 1N. acetic acid. The filtrate is evaporated dry and the product is recrystallized from a mixture of methyl alcohol and diethyl ether. M.p. product 205-t20bOs. Example 41. A solution of 3.1 g of benyl-3-Of Ll- (Dl-carbamoyl 3-cap6oxycipropyl) -carbamoylethyl-carbamoylmethyl4 -2-deoxy-2-isobutyroylamino-alpha O-glucopyranoside in 40 ml of a mixture of methyl alcohol and water 1 / 1 is hydrogenated in the presence of 10% palladium on carbon at atmospheric pressure and a temperature of 45 ° C. After treating the reaction mixture, 3-0-G L-1- (D-1-carbamoyl-3-carboxypropyl) -carbamoylethyl-carbamoylmethyl 7 is obtained. 2-deoxy-2-isobutyrylamino-P-glucose as a white powdery substance after sublimation drying. The starting material used was obtained by analogy with the method described in Example 40. Upon condensation of the sodium salt of benzyl-3-0-carboxymethyl-2-deoxy-2-isobutyroylamino-4, 6-0-isopropylidene-alpha-O-glucopyranoside with hydrochloride tert-butyl ester of L-alanyl-O-isoglutamine get tert-butyl exit benzyl-3-0-b- (D-1-to arbamoyl-3-to arboxypropyl) -carbamoylethylJ-carbamoylmethyl -2-deoxy -2 isobutyroylamine .o-4,6-0-isopropylidene-alpha-P-glucopyranoide in the form of a white foamy substance. Hydrolysis 4, b-0-isopr. group results in benzyl-3-0-l-1- (D-1-carbamoyl-3-carboxypropyl).-carbamoylethyl-carbamoylmethyl -2-deoxy-2-isobutyrylamino-alpha-D-glucopyranoside c Cj / - + 71 + 1 ° (methyl alcohol, from 0.956). The tert-butyl ester is cleaved with trifluoroacetic acid. Benzyl-3-0-1 - 1 - (D-1-carbamoyl-3-carboxypropyl) -carbamoyl ethyl} -carbamoylmethyl -2-deoxy-2-isobutyroyl-amino-alpha is obtained. -D-glucopyranoside as a white amorphous substance. Example 42. A solution of 4.2 g of benzyl-2-acetyl-N-methylamino-3-0-f L-1- (D-1-carbamoyl-3-carboxyproyl) -carbamoyl-3-carboxypropyl) -carbamoylethyl-carbamoylmethyl ) -2-deoxy-B-glucopyranoside in 75 ml of a mixture of methyl alcohol and water 1/1 is hydrogenated at atmospheric pressure and a temperature of 45 ° C in the presence of 0.5 g of 10% palladium on carbon. Then the catalyst is filtered off and the filtrate is evaporated to dryness. The residue is dissolved in a small amount of distilled water and freeze-dried, resulting in 2-acetyl-L-methylamino-3-0-CL-1-{D-1-carbamoyl-3-carboxypropyl) -carbamoylethyl-carbamylmethyl -2 -deoxy-0-glucose as a white powdery substance. Applied source material receive according to the following procedure. A solution of 8.5 g of benzyl-2-acetamino-2 deoxy-4, 6-0-isopropylidene-3-O-methoxycarbonylmethyl-alpha-O-glucopyranoside in 80 ml of absolute acetonitrile is mixed under nitrogen with stirring under conditions that exclude the presence of moisture. , with 0.75 g of sodium hydride and the reaction mass is stirred for 1 hour at 40 ° C. The reaction mixture is then cooled to room temperature and mixed with a solution of 4,0 g of iodide 1: p methiM in 50 for 4 hours ml of absolute acetonitrile. After stirring for an additional 3 hours, the reaction mixture is filtered and the filtrate is evaporated to dryness. The residue is dissolved in ethyl acetate, the resulting solution is washed with water, dissolved over sodium sulfate and evaporated to dryness. The result is benzyl-2-acetyl-N-methylamino-2-deoxy-4, 6-0-isopropylidene-3-0-methoxycarbonylmethyl-alpha-B-glucopyranoseId as a yellow colored oily substance with a value of Ri.0, 45 on a silica gel plate for thin layer chromatography in methylene chloride / ethyl acetate 85/15 system. A solution of 4.4 g of beNsyl-2-acetyl-N-methylamins-2-deoxy-4, 6-0-isopropyl- 3-O-methoxycarbonylmethyl-alpha-O-glucopyranoside in 60 mp of methyl alcohol and 15 ml of 1 N sodium hydroxide solution is kept for 1 hour at 1 g th re temperatures. Then the solution is mixed with 5 ml of 1N hydrochloric acid. And evaporated to dryness. The resulting sodium salt of benzyl-2-acetyl-No-methylamino-3-0-carboxymethyl-2-deoxy-4, 6-0-isopropylidene-alpha-B-glucopyranoside is dissolved in 50 ml of S, K-dimethylformamide and in the presence of 2 , 5 g of EEDQ condensate with 3.2 g of L-alanyl-O-isoglutamine tert-butyl ester hydrochloride. The reaction solution is then evaporated to dryness in vacuo and the residue is dissolved in ethyl acetate. The solution is washed with water, cooled with ice, 1N. a solution of hydrochloric acid, water, a saturated solution of sodium hydrogen carbonate and again with water, dried over magnesium sulphate and evaporated to dryness. The result is benzyl-2-acetyl-N-methylamino-3-0-1- (B-1-carbamoyl-3-carboxypropyl) -carbamoyl ethyl-carbamoyl-methyl -2-deoxy-4, 6-0 tert-butyl ester. -isopropylidene-alpha-P-glucopyranoside in the form of a yellow-colored foamy substance. The resulting product was dissolved in 45 ml of trifluoroacetic acid cooled to 95% and the reaction mixture was stirred for 1 hour at. Then the reaction mass is poured into 400 ml of absolute diethyl ether, the product precipitated is filtered off, washed with diethyl ether and dried. After treatment of the obtained substance with Dowex 3 acetate exchange resin in acetate form, benzoyl-2-acetyl-methylamino does not contain trifluoroacetic acid -3-0 (Dl-carbamate-3-carboxomespoil) -carbamoylethyl} -carbamoylmethyl -2-dexy-alpha-O-gl1ocopyranoside in the form of a white powdery substance. ... -. / In a similar way, 2-acetyl-L-methylamino-3-0-o-1- | 1, -1 - (B-1-carbamoyl-3-carboxypropyl) -carbamoylpropyl -carbamoyl ethyl -2-deoxy-0-glucose 2-acetyl-M-methyly-3-0- | L-1- (1) -1-carbamoyl-3-carboxypropyl) -carbamoylpropyl -carbamoylethyl -2-deoxy-0-glucose 2-acetyl-N-methylamino-3-0- f D-l-tL-l - ( p-1-carbamoyl-3-carboxypropyl) -carbamoyl-2-methylpropyl-carbamoyl and ethyl, -2-deoxy-O-glucose, 3-0-f I.- (D-1-carbamoyl-3-carboxypropyl) -carbamoylethyl ) -carbamoylmethyl -2-deoxy-2-prS) pionyl-N-methylamino-0 -glucose, 2-butyryl-N-methylamino-3-G JL-1- (D-1 -carbamoyl-3-carboxypropyl) - carbamoylethyl-carbamoylmethyl -2-deoxy-O-glucose. / Example 43. The trimethylsilyl ester can be obtained, for example, by the following procedure. 0.3 g of 2-benzamido-2-deoxy-3-0i-fCb-l-tD-1-carbamoyl-3-carboxypropyl drank) -carbamoyl ethyl 3 -carbamoyl-methyl-COO-glucose is dissolved in 3 ml of dimethylformamide and the solution is mixed with O ,, 4 ml of bis-trimethylsilylacetamide. After reacting for 5 hours, the reaction mass is evaporated to a syrupy state. From the resulting mass, the resulting acetamide can be precipitated by dissolving in absolute diethyl ether or absolute ethyl acetic acid. After re-evaporation, a colorless syrupy substance with N1 is obtained (dioxane with 0.8). In an analogous manner, 2-acetamino-2-deoxy-3-0-1-t (D-1-carbamoyl-3-trimethylsilylcarboxypropyl) -carbamoylethyl-carbamoylmethyl is obtained in the form of a syrupy substance; -1,4, b-Tris-trimethylsilyl-D-glucys with l1 d 10 (dioxane with 0.91). ; Upon contact with water, the trimethylsilyl ester groups are quickly saponified, so that it is also suitable for carrying out the coupling reaction. Example 44. A 5% solution of benzyl-2-acetamido-3-0-L-1- {0-1- (L-1-carboxyethyl) -carbamoyl-3-carboxypropyl-carbamoylethyl-J-carbamoyl-methyl-2-deoxy-alfa -D-glucopyranoside in a mixture of tetrahydrofuran and 2/1 water is hydrogenated at atmospheric pressure and room temperature in the presence of 10% palladium on carbon. After the theoretically calculated amount of hydrogen is consumed, the catalyst is filtered off from the reaction mixture and the filtrate is freeze-dried. As a result, 2-acetamido-3-O- - (L-1-carboxyethyl) -carbamoyl-3-carboxypropyl-carbamoylethyl is obtained. -carbamoylmethyl -2-deoxy-P-glucose as a white powdery substance. The TS.r value on the chromatogram in a thin layer (ethyl acetate / N. butyl alcohol / pyridine / acetic acid / water 42: 21: 21: 6slO). In a similar way, a derivative is obtained with muraminic acid itself. Source material can be obtained by the following method. 5.68 g of N-tert-β-butoxycarbonyl-b-alanyl-0-gamma-benzylglut-Min-b-alanine benzyl ester is dissolved in a mixture of 5 ml of trifluoroacetic acid and 5 ml of 1,2-dichloroethane and conditions excluding the presence of moisture. The reaction mixture is kept at room temperature for 16 hours. The reaction solution is then diluted with 50 ml of tetrahydrofuran, cooled in an ice bath, and then neutralized with triethylamine. After adding a solution of 3.7 g of benzyl-2-acetamido-3-carboxyl-2-deoxy-alpha-D-glucopyranoside and 1.38 ml of tri-. ethylamine in 100 ml of tetrahydrofuran, the resulting mass is mixed with 2.6 g of 2-acetoxy-S-ethoxycarbonyl-1,2-dihydroquinoline and kept at room temperature for 24 hours. The residue obtained after distilling off the solvent was dissolved in a mixture of chloroform. and methyl alcohol 9/1, the solution is washed with water, cooled with ice 2 n, hydrochloric acid solution, water, saturated sodium bicarbonate solution and again with water, filtered and freed from solvent. The result is benzyl-2-acetamido-5-0-G LI-DI- (L-1-carboxyethyl) -carbamoyl-3-carboxypropyl-carbamoyl ethyl-carbamoylmethyl -2-deoxy-alpha-O-glucopyranoside in the form of a colorless powdery substance R 0.48 (in identical system).
Applied source material can be obtained by the following method.
7.15 g of l-tert-butoxycarbonyl-b-alanine-D-α-glutamic acid gamma-benzyl ester and 6.15 g of benzyl-and-roan-L-alanine paratoluene sulphonate are dissolved in 100 ml of anhydrous dimethylformamide. The solution is cooled in a bath with ice and at. 4.08 g of N-oxysuccinimide, .3.61 g of dicyclohexycarbodiimide, and 1.95 ml of N-methylmorpholine are added to it by stirring. The reaction mass is still stirred, 6 hours at OC and 15-4 at room temperature, after which the suspension is cooled, the residue is filtered (dicyclohexylurea and morpholine hydrochloride) and the filtrate is evaporated. The residue is dissolved in ethyl acetate, washed several times with water, 1N. citric acid solution and 1 n. with a solution of sodium carbonate and water. A solution of the product in ethyl acetate is dried, evaporated and the crystalline residue is recrystallized from a mixture of ethyl acetate and petroleum ether 1/1. M.p. products 135-136 s, 9 + 1 ° (methyl alcohol, 1), Rp 0.82 (in the indicated system solvent) and 0.85 (acetonitrile / water 3: 1).
Instead of alanine, the protected dipeptide can similarly be extended by other natural L-amino acids. Example 45. 7.5-10 dead parasites Tripanosoma cruzi (the causative agent of Chagas disease) are suspended in a solution of 50 mg of N-oxysuccinimido. 2nd ester 2-acetamino-3-0-1 -
0 - (D-carbamoyl-3-carboxypropyl) -carbamoylethyl-carboamoylmethyl -2-deoxy-D-glucose in 6 ml of physiological buffer solution. Suspension maintain 2 h at. After this 5 | GO, the parasites associated with muramyl dipeptide are sedimented by centrifugation. The precipitate is washed by. means of re-suspension. in physiological buffer solution
Q and centrifugation. The washed parasite addition product with muramildipeptide is suspended in physiological buffer solution and used for immunization.
The quantitative determination of muradi, mildipeptide bound to trypanosomes is carried out by analogy with that described in Example 1 using the Morgan a-Elonson reaction, resulting in 50-70 mg of muramyl dipeptide per mg of trypanosome.

权利要求:
Claims (1)
[1]
METHOD FOR PRODUCING ARBITRAL ι NEW MURAMYLPEPTIDANTIGENS of structural formula (I)
A - (Z - MPj _h ,
where A is the antigen residue: serum albumin, erythrocyte membranes: erythrocyte polysaccharide, Neisseria mehingitidis polysaccharide, malaria pathogens, T-lim, phoblasts, breast cancer cells, foot and mouth disease vaccines, rabies, influenza antigens, tetanus and cholera toxoid, eicosapeptide, parasites Tri-ponosoma "cruzi, Z = 0 (which corresponds to a direct bond between the antigen and muramyl peptide), the remainder of the nitrogen atom bound to C, C-diaminoalkane (Cd-ϊ), alkanedicarbonyl (C ^ d) or οί , β or J * aminoalkanecarbonyl (C);
MR - the remainder of the muramyl peptide of the formula (II)
ORi (where X * is carbonyl, carbonyloxy or sulfonyl group;
R., R. | H Ry is hydrogen or trimethylsilyl;
Rj is phenyl, unsubstituted lower alkyl or lower alkyl substituted with hydroxyl, carboxyl or alkoxycarbonyl. (FROM ,
R_, Rg, Rg and R {j is hydrogen or C ^ -Cj alkyl;
Ry is hydrogen, C ^ -C ^ -alkyl, C <-C ^ -oxyalkyl free, esterified into 'ether or ester, free, C <-C5-mercaptoalkyl, free or acylated C * esterified into ether or ester -C, aminoalkyl, chloromethyl, phenyl, benzyl or η-hydroxybenyl; I
K. R _<0 and R | - independently from each other I. Free esterified I ester or | amidated carboxyl;
Rjo is also hydrogen;
| η is an integer of 0, provided that 1 mg or 10 * antigen cells respectively contain from 0.01 to 0.5 mg of muramyl peptide in the compounds of structural formula (I), g
Ιω is also distinguished by the fact that the antigen is condensed with a 5-150-fold excess of the murapyl peptide of formula (II) bound to Z having the indicated meanings, and the muramyl peptide bound to the Z moiety contains a carboxyl group or an activated ester group of a carboxylic acid and the antigen contains at least at least one free amino, hydroxy or mercapto group, or the muramyl peptide bound by a Z moiety contains a free amino group and an antigen, at least one free carbo-xyl or activated carbon ester group slots, at a temperature of 0-40 ° C in water or an aqueous buffer at pH 5-9 for a period of time from 5 minutes to 48 hours, by the method of activated esters or carboch: by the imid method.
Priority according to the rules of the faith:
02.24.78. with compounds of forms, ulas (I), where A is serum albumzin, erythrocyte membranes, polysaccharis. Neisseria meningitidis, merozoite * malaria pathogens, T-lymphoblus': you, 07.04 .78. with compounds of forgmula (I), where A is breast cancer cells, foot and mouth disease vaccines, rabies vaccines, anti-influenza virus anti-influenza
05/18/78. with compounds of the formula (I), where A are tetanus and cholera toxoids, eicosapeptide, or tripanosoma cru2i parasites.
.1

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同族专利:

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公开号 | 公开日

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FI66878B|1984-08-31|

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NO790626L|1979-08-27|

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EP0003833B1|1983-07-20|

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EP0003833A2|1979-09-05|

---

HU182011B|1983-12-28|

---

GB2015534A|1979-09-12|

---

IL56724D0|1979-05-31|

---

ATA142079A|1981-04-15|

---

DK79779A|1979-08-25|

---

DD141616A5|1980-05-14|

---

JPH0130809B2|1989-06-22|

---

ES477977A1|1980-01-16|

---

FI66878C|1984-12-10|

---

ZA79893B|1980-03-26|

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IL56724A|1982-12-31|

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DK161026B|1991-05-21|

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JPS54141718A|1979-11-05|

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CA1138436A|1982-12-28|

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AU4454679A|1979-08-30|

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GR77615B|1984-09-25|

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AT364718B|1981-11-10|

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NO151088C|1985-02-06|

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NO151201C|1985-02-27|

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AU527549B2|1983-03-10|

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ES483558A1|1980-04-16|

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FI790584A|1979-08-25|

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PL123315B1|1982-10-30|

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PL213696A1|1980-07-14|

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NO793993L|1979-08-27|

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EP0003833B2|1990-12-19|

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NO151088B|1984-10-29|

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NO151201B|1984-11-19|

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AR223833A1|1981-09-30|

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NZ189756A|1982-05-31|

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EP0003833A3|1980-02-06|

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DK161026C|1991-10-28|

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PT69281A|1979-03-01|

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US4186194A|1973-10-23|1980-01-29|Agence Nationale De Valorisation De La Recherche |Water soluble agents effective as immunological adjuvants for stimulating, in the host the immune response to various antigens and compositions, notably vaccines containing said water soluble agents|

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CH613709A5|1975-12-10|1979-10-15|Ciba Geigy Ag|Process for the preparation of glucosamine derivatives|

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GB1573126A|1976-03-10|1980-08-13|Anvar|Immunising and anti-infectious adjuvant agents comprising peptide derivatives of muramic acid|

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FR2522967B1|1982-03-15|1986-03-07|Anvar|CONJUGATES OF HAPTENES AND MURAMYL-PEPTIDES, WITH IMMUNOGENIC ACTIVITY AND COMPOSITIONS CONTAINING THEM|

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US4587046A|1982-05-18|1986-05-06|The Regents Of The University Of California|Drug-carrier conjugates|

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FR2558165B1|1984-01-17|1986-07-04|Anvar|NOVEL CONJUGATES OF OLIGO-MURAMYLPEPTIDES AND BIOLOGICAL COMPOSITIONS CONTAINING THEM FOR THE ACTIVATION OF MACROPHAGES|

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FR2569984B1|1984-09-12|1987-08-14|Anvar|SYNTHETIC MOLECULE CONTAINING A PLURALITY OF SEPARATE EPITOPES, PROCESS FOR OBTAINING SAME AND APPLICATION TO THE PRODUCTION OF POLYVACCINES|

法律状态:

优先权:

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申请号 | 申请日 | 专利标题

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CH203578|1978-02-24|

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CH377778|1978-04-07|

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CH539478|1978-05-18|

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