Novel aromatic derivatives substituted by a ribose, their method of preparation and application as medicine

Abstract

The invention relates to compounds of general formula (I) and their salts, where in the formula R1 represents a hydrogen atom, a hydroxyl group, an optionally substituted alkyl, alkenyl or alkynyl group, or an alkoxy group; R2 represents a hydrogen or halogen atom; R3 represents a hydrogen or halogen atom; or an alkyl group; R4 represents a group of general formula NRgRh, where Rg and Rh are the same or different and their meaning is: a hydrogen atom, an alkyl, aryl or heterocyclic group; R5 represents a hydrogen atom or an O-alkyl group; R6 represents an alkyl or CH2-O-alkyl group; and R7 represents a hydrogen atom or an alkyl group. The compounds of general formula (I) have antibiotic properties and also exert an inhibitory effect on the gyrase enzyme. à

Description

The invention relates to novel aromatic derivatives substituted with ribose, to a process for their preparation, and to their use as pharmaceuticals. US Patent No. 4,226,978 describes aminoglycoside antibiotics labeled with β-galactosyl-umbelliferone, such as gentamicin, which are useful in homogeneous and heterogeneous specific binding assays of such antibiotics in liquid media, such as sera, and β-galactosyl-umbelliferone carboxylic acid and its salts, which are useful as intermediates in the process for preparing the labeled antibiotics. The structure of the compounds forming the subject of the invention is illustrated by the general formula (I), where Rj represents a hydrogen atom; a hydroxyl group; an alkyl, alkenyl or alkynyl group optionally interrupted by an oxygen, sulfur or nitrogen atom, having up to 12 carbon atoms, a straight or branched carbon chain or a cyclic group optionally substituted by one or more halogen atoms, one or more hydroxyl groups, C=N, NO2, NR^ groups, where Ra and Rba are single or different and represent a hydrogen atom; an alkyl group containing up to 8 carbon atoms; or Ra and Rba together with the nitrogen atom to which they are attached may also form a heterocyclic group containing an additional nitrogen, sulfur or oxygen atom; or Rj is an alkoxy group containing up to 8 carbon atoms, optionally substituted with one or more of the above substituents; or R, is a group of the general formula NR^, in which R and R are identical or different and represent a hydrogen atom; or an alkyl group of up to 12 carbon atoms, optionally interrupted by oxygen, sulfur or nitrogen atoms, optionally substituted with one or more of the above substituents; or Rc and Rc may also form a heterocyclic group with the nitrogen atom to which they are attached, optionally containing a nitrogen, sulfur or oxygen atom as an additional heteroatom; X represents an oxygen atom; or a group of the general formula N-Nalk! or NOalk2, where alk! and alk2 are alkyl groups optionally interrupted by oxygen, sulfur or nitrogen atoms, containing up to 12 carbon atoms, optionally substituted by one or more halogen atoms, one or more groups of the general formula NReRf, in which R and Rf are the same or different and represent a hydrogen atom; an optionally substituted alkyl group containing up to 8 carbon atoms; or Reés gasal, together with the nitrogen atom to which they are attached, can also form a heterocyclic group, which may contain an oxygen, sulfur or nitrogen atom as an additional heteroatom; R2 represents hydrogen or halogen; R3 represents hydrogen or halogen; or an alkyl group containing up to 8 carbon atoms; R4 means a group of general formula NRgRb, in which R and R may be identical or different and represent a hydrogen atom; a straight or branched chain or cyclic aryl or heteroaryl group containing up to 8 carbon atoms, optionally substituted; or Rg and Rh may also form, together with the nitrogen atom to which they are attached, a heterocyclic group which may contain an additional oxygen, sulfur or nitrogen atom; or R4 represents an aryl or heteroaryl group optionally substituted with one or more halogen atoms, one or more hydroxyl groups, one or more alkyl or alkoxy groups having up to 8 carbon atoms; R} is hydrogen; O-alkyl containing up to 4 carbon atoms; R6 is alkyl or CH2-O-alkyl, wherein the alkyl group has up to 8 carbon atoms; and R7 is hydrogen; or an alkyl group containing up to 8 carbon atoms. The invention also extends to salts of the above compounds. Examples of salts include sodium, potassium, lithium, calcium and magnesium salts, and salts with nitrogen-containing bases such as trimethylamine, triethylamine, methylamine, propylamine, N,N-dimethylethanolamine or tris(hydroxymethyl)methylamine. Examples of salts include those formed with the following acids: acetic acid, propionic acid, trifluoroacetic acid, maleic acid, tartaric acid, methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, phosphoric acid, and especially stearic acid, ethylsuccinic acid and laurylsulfonic acid. Substituents are defined as follows: - the alkyl, alkenyl or alkynyl group is preferably a methyl, ethyl, propyl, isopropyl, η-butyl, isobutyl, tert-butyl, decyl or dodecyl group; a vinyl, allyl group; an ethynyl, propynyl group; a cyclobutyl, cyclopentyl or cyclohexyl group; - the halogen atom is preferably a fluorine, chlorine or bromine atom; - the aryl group is preferably a phenyl group; - the heterocyclic group is preferably a pyrrolyl, pyrrolidinyl, pyridinyl, pyrazinyl, pyrimidinyl, piperidinyl, piperazinyl, quinuclidinyl, oxazolyl, isoxazolyl, morpholinyl, indolyl, imidazolyl, benzimidazolyl, triazolyl, thiazolyl, azetidinyl or aziridinyl group. Examples of preferred compounds according to the invention include those in which R2 is hydrogen; in which R3 is methyl; in which R7 is hydrogen or methyl; and in which R5 is methoxy. A very particular subject of the invention are those compounds of formula (I) wherein R4 represents a group of formula (a); and also those wherein it represents an NH-cyclopropyl group. Among the compounds of the invention, we particularly mention those compounds of formula (I) which HU 222 787 Bl where X represents an oxygen atom; those where X represents a NOR group, where R represents an alkyl group optionally substituted by one or more halogen atoms, optionally interrupted by oxygen, nitrogen, sulfur atoms, and optionally carrying an optionally substituted heterocyclic group, for example, where X represents a NOCH3 group; further preferred compounds include those compounds of formula (I) where Rj represents an alkyl group optionally interrupted by oxygen or sulfur atoms; or an O-alkyl group optionally interrupted by oxygen or sulfur atoms; an NH2 group; for example, those compounds where Rj represents a CH3, -CH2-S-CH3, -CH2-O-CH2-CH3, NH2, OC2H5 or -CH2-CH(CH3)2 group; and those compounds of formula (I) where Rj represents a methyl or O-ethyl group may be particularly highlighted. Among the preferred compounds according to the invention, the following compounds can be particularly highlighted: - 3-acetyl-7-[(6-deoxy-5-C-methyl-4-O-methyl-α-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl2H-1-benzopyran-2-one-(5-methyl-1H-pyrrole-2-carboxylic acid-3')-ester; - ethyl 7-[(6-deoxy-5-C-methyl-4-O-methyl-α-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-2oxo-2H-1-benzopyran-3-carboxylate-(5-methyl-1H-pyrrole-2-carboxylic acid-3')-ester; -7-[(6-Deoxy-5-C-methyl-4-O-methyl-α-L-lyxohexopyranosyl)oxy]-4-hydroxy-3-[1-(methoxyimino)ethyl]-8-methyl-2H-1-benzopyran-2-one(5-methyl-1H-pyrrole-2-carboxylic acid-3') ester; - 7-[(6-deoxy-5-C-methyl-4-O-methyl-α-L-lyxohexopyranosyl)oxy]-3-(ethoxyacetyl)-4-hydroxy-8methyl-2H-1-benzopyran-2-one-(5-methyl-1H-pyrrole-2-carboxylic acid-3')-ester; - 3-(cyclopropylcarbonyl)-7-[(6-deoxy-5-C-methyl4-O-methyl-aL-lyxohexopyranosyl)oxy]-4-hydroxy-8-methyl-2H-1-benzopyran-2-one-(5-methyl1H-pyrrole-2-carboxylic acid-3')-ester; and - 7-[(6-Deoxy-5-C-methyl-4-O-methyl-αL-lyxohexopyranosyl)oxy]-4-hydroxy-8-methyl-2-oxo2H-1-benzopyran-3-carboxamide-(5-methyl-1H-pyrrole-2-carboxylic acid-3')-ester. The compounds of general formula (I) exert a very favorable antibiotic effect on Gram-positive bacteria, such as staphylococci, streptococci, pneumococci, enterococci, listeria, and anaerobes. Based on all this, the compounds of the invention can be used as a medicine in the treatment of infections caused by sensitive germs and in particular staphylococci. Such staphylococcal infections are staphylococcal blood poisoning, malignant staphylococcal infections of the face or skin, purulent dermatitis, infected or suppurating wounds, furuncles, anthrax, purulent connective tissue inflammation (phlegmon); impetigo and acne; also acute primary or post-influenza angina, focal pneumonia, pulmonary suppuration; streptococcal infections, such as acute angina, otitis media, sinusitis, scarlet fever; pneumococcal infections, such as pneumonia, bronchitis and diphtheria. The substances of the invention are also effective against infections caused by Haemophilus influenzae and similar infectious germs. Accordingly, the invention also relates to the use of compounds of general formula (I). The invention also particularly relates to the use of the above-mentioned preferred compounds as medicaments. The invention also relates to pharmaceutical compositions which contain as active ingredient at least one pharmaceutically acceptable compound as defined above. These preparations may be administered orally (buccally), rectally (rectally), parenterally or topically (locally) to the skin and mucous membranes, the preferred route of administration being oral. These preparations may be solid or liquid and may take the form of a pharmaceutical form currently used in human medicine, such as plain or sugar-coated tablets, capsules, granules, suppositories; injectable preparations, ointments, creams, gels; all of these pharmaceutical forms may be prepared by conventional methods. The active ingredient or ingredients may be incorporated into excipients commonly used in such pharmaceutical preparations. Examples of such excipients include: talc, gum arabic, lactose, starch, magnesium stearate, cocoa butter; aqueous and non-aqueous carriers, fatty substances of vegetable or animal origin, paraffin derivatives, glycols, as well as various wetting, dispersing, emulsifying and preserving agents. These compositions may also be in powder form for reconstitution with a suitable vehicle, such as non-pyrogenic, sterile water, immediately before use. The dose to be administered in a given case varies depending on the disease to be treated, the patient, the route of administration and the selected active ingredient: for example, it may vary between 50 mg and 3000 mg daily for adult patients, administered orally or by injection. The invention also includes a process for preparing the compounds of the invention. This process comprises the steps of: preparing a compound of formula (II) wherein Rg is a free or protected hydroxyl group; Z is hydrogen or a group of formula C(=X)-R,; X, R1;R2 and R3 are as defined above; OR9 is a free or protected hydroxyl group - a compound of formula (III) is reacted, wherein R5, Rg and R7 are as defined above; OR'4 is a protected hydroxyl group; R"4 is a hydrogen atom; or R'4 and R"4 together with the carbon atom to which they are attached may also form a group of formula (b), thus obtaining a compound of formula (IV) where the substituents are as defined above; - then the compound of general formula (IV) thus obtained is taken to the following steps (or to one or more of these steps); - the hydroxyl group attached at the 4-position is optionally replaced by the hydroxyl group in the α-position of the OR'4 group After protection of the hydroxyl group of the sugar HU 222 787 B1 - it is released; - if Z represents a hydrogen atom, then - optionally after protection of the reactive hydroxyl groups, a group of the general formula -C(=X)-R is introduced; - by replacing the group of general formula R'4, the group of formula C(=O)-R4 is introduced; - group X is modified. The starting materials of the process according to the invention, i.e. the compounds of general formulae (II) and (III), are new products; examples of their preparation are given in the experimental part. The compounds of general formula (IV) obtained by carrying out the process according to the invention are novel. Accordingly, the compounds of general formulae (II), (III) and (IV) - as new chemical products - also form the subject matter of the invention. According to a preferred embodiment of the method according to the invention - the reaction of compounds of general formula (II) with compounds of general formula (III) is carried out in the presence of a dialkyl azodicarboxylate, for example diethyl or diisopropyl azodicarboxylate; - the optional liberation of the hydroxyl group in the 4-position of the coumarin ring is carried out by hydrogenolysis or isomerization and subsequent hydrolysis; - the remaining protected hydroxyl groups are released by acidic hydrolysis, for example in the presence of p-toluenesulfonic acid; - the introduction of the group of general formula C(=X)-R! - when Z represents a hydrogen atom - is carried out by acylation and subsequent transposition (relocation); - glycosylation is carried out by Mitsunobu reaction; - the other modifications are carried out under standard conditions. The invention is described in detail in the following non-limiting examples. Production example 1 Preparation of 6-Deoxy-5-C-methyl-4-O-methyl-L-lyxo-hexopyranose-[3(5-methyl-1H-pyrrole-2-carboxylate)]-ester Step A: Benzyl-6-deoxy-5-C-methyl-4-O-methyl-L-lyxo-hexopyranoside Hydrogen chloride gas is bubbled into a suspension of 6-deoxy-5-C-methyl-4-O-methyl-L-lyxo-hexopyranoside and 400 ml of benzyl alcohol for 2 hours at a temperature of 20-22 °C. Then 120 ml of demineralized (demineralized) water and 40 g of sodium carbonate are added, followed by 240 ml of ethyl acetate. The mixture is decanted, extracted with ethyl acetate, and the combined organic phase is washed with saturated brine. The organic solution is dried, filtered, and the resulting solution is evaporated under vacuum at a pressure of 4.5-5 kPa while stirring. Thus, 118.8 g of product is obtained, which is chromatographed on silica gel. Elution was carried out with a 95:5 mixture of dichloromethane (abbreviated: DCM) and methanol to give 109.9 g of the desired product. Step B: Benzyl-2,3-O-carbonyl-6-deoxy-5-C-methyl-4-O-methyl-L-lyxohexopyranoside To a solution of 109 g of the product obtained in step A) and 1100 ml of 1,2-dichloroethane, 67.5 g of 1,1-carbonyldiimidazole are added and the reaction mixture is refluxed for 2 hours. The temperature is then cooled to 20-22 °C and the reaction mixture is evaporated to dryness in vacuo at 25-30 °C. The 200.8 g of product thus obtained is chromatographed on silica gel, eluting with a 99:1 mixture of DCM and methanol, to give 91.6 g of the desired product. IR spectrum: ketone 1813 cm-1 benzyl 1498 cm-1 The 2-methyl-1H-pyrrole derivative used in step (C) is prepared as follows: 750 g of pure potassium hydroxide are added to a suspension of 370 g of pyrrole-2-carboxaldehyde and 5 liters of ethylene glycol, then 544 ml of 64% hydrazine hydrate are added to the suspension over 30 minutes. The reaction mixture is then refluxed for 90 minutes and 2 liters of demineralized water are added and poured into a mixture of ice and water. Extraction is carried out with DCM, the organic phase is dried, filtered and the solution is evaporated to dryness. 270.3 g of product are thus obtained, which is distilled at 1.5 kPa to give 227 g of the desired product, boiling point 46-47 °C at 1.5 kPa. Step C: Benzyl-6-deoxy-5-C-methyl-4-Omethyl-L-lyxohexopyranoside [3-(5-methyl-1H-pyrrole-2-carboxylate)] ester A solution of 60.2 g of 2-methyl-1H-pyrrole in 460 ml of diethyl ether is added to 248 ml of 3 molar ethereal methyl magnesium bromide solution at 0-2 °C over 1 hour. The reaction mixture is kept at 0-2 °C for 30 minutes while stirring, then 460 ml of toluene are added thereto over 15 minutes. Stirring is continued for another 15 minutes at 0±2 °C, then a solution of 91.3 g of the product prepared in the previous step B) and 460 ml of toluene is added thereto over 45 minutes. Stirring is continued for another 2 hours at 0±2 °C, then the reaction mixture is poured into an aqueous solution of ammonium chloride, decanted and extracted with ethyl acetate. The organic phase is washed, dried and the resulting filtrate is evaporated to dryness in vacuo. The 134.6 g of product thus obtained is chromatographed on silica gel. A mixture of DCM and acetone in a ratio of 8:2 and then a mixture in a ratio of 9:1 is used as the eluent, and thus the desired product is obtained. Step D: 6-Deoxy-5-C-methyl-4-O-methyl-L-lixohexopyranose-[3-(5-methyl-1H-pyrrole-2-carboxylate)] ester To a solution of 72.4 g of the product prepared in step C) above and 1.45 liters of denatured 100% ethanol, 14.7 g of 10% palladium-on-carbon catalyst are added, the reaction mixture is stirred under hydrogen pressure for 1 hour at a temperature of 60-62 °C, and then the reaction mixture is allowed to cool to ambient temperature. At this time, another 1 g of 10% palladium-on-carbon catalyst is added, and stirring is continued under hydrogen pressure for 1 hour. The temperature is reduced to 20-22 °C, and the solution obtained after filtration and washing is evaporated to dryness. Thus, 57 g of ki4 HU 222 787 B1 The desired product is obtained, i.e. the title compound of Preparation Example 1 is obtained. Production example 2 Preparation of 7-Hydroxy-8-methyl-4-(2-propenyloxy)-1H-1-benzopyran-2-one Step A: 1-[2-Hydroxy-3-methyl-4-(tetrahydro-2H-pyran-2-yl)oxy]phenylethanone A mixture of 200 g of l-(2,4-dihydroxy-3-methyl)phenylethanone and 1.2 liters of diethyl ether is cooled to 8 °C, 200 ml of dihydro-2Hpyran and 1 g of p-toluenesulfonic acid (abbreviated: PTSA) are added. The reaction mixture is allowed to warm to room temperature and stirring is continued for 3 hours, then 253 mg of PTSA are added. The product thus obtained is poured into 400 ml of a molar aqueous potassium dihydrogen phosphate solution. After decantation, the organic solution is washed with water and dried. After evaporation, 302.5 g of the desired product is obtained in crude form, and its purification is carried out as follows: the product is dissolved in 2 liters of DCM, the organic phase is washed with a tenfold diluted ammonium hydroxide solution, then with a concentrated sodium chloride solution, after drying, it is filtered and evaporated to dryness. Thus, 272.55 g of the desired product is obtained. Step B: 4-Hydroxy-8-methyl-7-[(tetrahydro-2H-pyran-2-yl)oxy]-2H-1-benzopyran-2-one A mixture of 750 ml of toluene, 129.9 g of the product obtained in the previous step A) and 126 ml of diethyl carbonate in 620 ml of toluene is heated to 90 °C and 52 g of sodium hydride are added in the form of a 55% oil suspension while maintaining the temperature at 90 °C. The reaction mixture is stirred at 90 °C and then allowed to cool to room temperature. At this time, 10 ml of ethanol are added, filtered, washed with diethyl ether and then separated. The entire product is poured into 1 liter of molar aqueous sodium dihydrogen phosphate solution and, after separation, rinsed with water, then with acetone and finally with diethyl ether. The product obtained is dried over phosphorus pentoxide at 50 °C to give 141.89 g of the desired product. Step C: 8-Methyl-4-(2-propenyloxy)-7-[(tetrahydro-2H-pyran-2-yl)oxy]-2H-1-benzopyran-2-one To a mixture of 13.814 g of the product obtained in the previous step, 4.07 ml of allyl alcohol, 15.74 g of triphenylphosphine and 150 ml of DCM at 0 °C, 9.45 ml of diethyl azodicarboxylate are added, and the reaction mixture is stirred for 15 minutes at 0 °C and then for 2 hours at ambient temperature. At this time, another 5.25 g of triphenylphosphine, 1.36 ml of allyl alcohol and 3.15 ml of diethyl azodicarboxylate are added. The reaction mixture is stirred for 2 hours at ambient temperature, then evaporated, and the product thus obtained is chromatographed on silica gel. Using a 3:1 mixture of hexane and ethyl acetate as eluent, 7.85 g of the desired product are obtained. Step D: 7-Hydroxy-8-methyl-4-(2-propenyloxy)2H-1-benzopyran-2-one To a mixture of 7.80 g of the product obtained in the previous step and 150 ml of tetrahydrofuran (abbreviated: THF) 100 ml of 1 molar HCl solution are added and the mixture is stirred for 6 hours at ambient temperature. At this time, saturated sodium chloride solution is added and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and evaporated to dryness. The residue is dried to give 4.40 g of the desired product, i.e. the title compound of Preparation Example 2; Rf value 0.26 (developing agent hexane and ethyl acetate in a 1:1 ratio). Example 1 Preparation of 7-[(6-Deoxy-5- C-methyl-4-O-methyl-aL-lyxo-hexopyranosyl)-oxy]-4-hydroxy-8-methyl-3-[(methylthio)-acetyl]-2H-l-benzopyran-2-one-(5-methyl-lH-pyrrole2-carboxylic acid-3)-ester Step A: 7-[(6-Deoxy-5-C-methyl-4-O-methyl-vL-lyxo-hexopyranosyl)-oxy]-8-methyl-4-(2-propenyloxy)-2H-1-benzopyran-2-one g Final product of Preparation Example 1, 4.65 g Final product of Preparation Example 2, 5.26 g A mixture of triphenylphosphine and 500 ml of DKM is thoroughly mixed, then 4 ml of diisopropyl azodicarboxylate is added at 0 °C. The mixture is stirred for 1 hour at ambient temperature, then 2.19 g of triphenylphosphine and 1.65 g of diethyl azodicarboxylate are added. Stirring is continued for 1 hour at ambient temperature, then an additional 2.19 g of triphenylphosphine and 1.65 ml of diisopropyl azodicarboxylate are added to the mixture. The mixture is washed with aqueous sodium dihydrogen phosphate solution, then with brine, the organic phase is dried, concentrated, and evaporated to dryness. The residue is chromatographed on silica gel, eluting with a 60:40 mixture of hexane and ethyl acetate, to give 3.51 g of product “A”, which is thoroughly triturated with diethyl ether, separated, and dried.Thus, the desired product is obtained in crude form in a yield of 3.0 g. On the other hand, 3.24 g of the product 3” is obtained, which is chromatographed on silica gel and eluted first with a mixture of DCM and ethyl acetate 90:10, then 80:20; then the elution is continued with a mixture of DCM, ethyl acetate and THF 70:20:10. Thus, 0.88 g of the product is obtained, which is purified by ultrasonication in diethyl ether. After separation, the desired product is obtained in crude form (as 2nd generation). The two crude desired products were combined, triturated thoroughly with diethyl ether, separated and dried to give the desired product, the title product of step A), in a yield of 3.625 g. Step B: 7-{[6-Deoxy-5-C-methyl-4-O-methyl-2O-(tetrahydro-2H-pyran-2-yl)-aL-lyxohexopyranosyl]oxy}-8-methyl-4-(2-propenyloxy)-2H-1-benzopyran-2-one-(5-methyl1H-pyrrole-2-carboxylic acid-3')-ester 200 mg of PTSA and 11 g of the product obtained in the previous step A) are added to 3.77 ml of dihydro-(2H)-pyran. The reaction mixture is stirred at ambient temperature for 2 hours, then treated with saturated sodium bicarbonate solution, after extraction with DCM, the organic phases are combined, dried, the solvent is evaporated to dryness, and the residue is thoroughly triturated with a 3:1 mixture of hexane and ethyl acetate. After separation and drying, 8.40 g of the desired product is obtained. Step C: 7-{[6-Deoxy-5-C-methyl-4-O-methyl-2O-(tetrahydro-2H-pyran-2-yl)-α-L-lyxo5 HU 222 787 B1 hexopyranosyl]-oxy}-4-hydroxy-8-methyl2H-1-benzopyran-2-one-(5-methyl-1H-pyrrole-2-carboxylic acid-3)-ester 5.88 ml of isopropylamine and 1.67 g of palladium tetrakis(triphenylphosphine) were added at 0 °C to a solution of 8.90 g of the product obtained in the previous step and 90 ml of THF. The reaction mixture was stirred at 0 °C for 20 min and then added to a mixture of 50 ml of aqueous sodium hydrogen sulfate solution and 100 ml of a 1:2 hexane-ethyl acetate mixture. The aqueous phase was extracted with a 1:2 hexane-ethyl acetate mixture, the organic phases were combined, dried and the solvents were evaporated. The residue was chromatographed on silica gel, eluting with a 95:5 mixture of DCM and methanol, to give 2.50 g of the desired product; Rf=0.22 (DCM / methanol 95:5). Step D: 7-{[6-Deoxy-5-C-methyl-4-O-methyl-2O-(tetrahydro-2H-pyran-2-yl)-a.-L-lyxohexopyranosyl]oxy}-4-hydroxy-8-methyl-3[(methylthio)acetyl]-2H-1-benzopyran-2-one-(5-methyl-1H-pyrrole-2-carboxylic acid-3')ester To a solution of 400 mg of the product prepared in the previous step and 5 ml of anhydrous DCM, 67 μΐ 2-methylthioacetic acid, 280 mg of 4-(dimethylamino)pyridine and 147 mg of N-(3dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride are added. The reaction mixture is stirred for 18 hours at ambient temperature, then diluted with 100 ml of ethyl acetate, and then washed first with an aqueous solution of sodium hydrogen sulfate, then with water, finally with a concentrated brine solution, dried, filtered and evaporated to dryness. The 401 mg of product thus obtained is purified by chromatography. Using a 98:2 mixture of chloroform and methanol as eluent, 324 mg of the desired product is obtained after drying, the Rr value of which is 0.68 (eluent: 95:5 mixture of DCM and methanol). Step E: 7-[(6-Deoxy-5-C-methyl-4-O-methyl-αL-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-3-[(methylthio)acetyl]-2H-1-benzopyran-2-one-(5-methyl-1H-pyrrole-2-carboxylic acid-3')-ester To a solution of 293 mg of the product obtained in the previous step in 10 ml of methanol was added 60 mg of PTSA and the reaction mixture was stirred at ambient temperature for 5 hours. The reaction mixture was diluted with a 67:33 mixture of ethyl acetate and hexane, washed with dilute sodium bicarbonate solution, then rinsed with water and brine. The product was dried and evaporated to dryness to give 227 mg of material which was chromatographed on silica gel. Using a 93:7 mixture of chloroform and methanol as eluent, 171 mg of crude desired product was obtained, which was eluted on silica gel with a 94:6 mixture of chloroform and methanol. In this way, the desired product was isolated, which had an Rf value of 0.42 (chloroform / methanol 94:6). H-NMR spectrum (300 MHz, DMSO-d6, δ ppm): 1.06 (s, 3H), 1.31 (s, 3H), 2.11 (s, 3H), 2.23 (s, 3H), 2.25 (s, 3H), 3.47 (s, 3H), 3.66 (d, 1H, J=10 Hz), 3.92 (AB, 2H, J=14.0 Hz), 4.19 (s, 1H), 5.48 (dd, 1H, J=3.0 and 10.0 Hz), 5.70 (d, 1H, J=2.5 Hz), 5.74 (m, 1H), 5.93 (m, 1H), 6.79 (m, 1H), 7.26 (d, 1H, J=9.0 Hz), 7.94 (d, 1H, J=9.0 Hz), 11.66 (broad s, 1H). Example 2 Preparation of 7-[(6-Deoxy-5-C-methyl-4-O-methyl-aL-lyxo-hexopyranosyl)-oxy]-3-(ethoxyacetyl)-4-hydroxy-8methyl-2H-l-benzopyran-2-one-(5-methyl-lH-pyrrole-2-carboxylic acid-3)-ester Step A: 7-{[6-Deoxy-5-C-methyl-4-O-methyl-2O-(tetrahydro-2H-pyran-2-yl)-a.-L-lyxo-hexopyranosyl]-oxy}-3-(ethoxyacetyl)-4-hydroxy-8-methyl-2H-1-benzopyran-2-one-(5methyl-1H-pyrrole-2-carboxylic acid-3)-ester To a solution of 300 mg of the product prepared in step C of the previous example, 210 mg of 4-(dimethylamino)pyridine (abbreviated: DMAP) and 110 mg of N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide, 55 μΐ of 2-ethoxyacetic acid are added. The reaction mixture is stirred at ambient temperature for 18 hours, then diluted with 100 ml of ethyl acetate, washed with 10% aqueous sodium hydrogen sulfate solution, then with water, and finally with concentrated brine. The organic phase is dried, filtered, and evaporated. The 362 mg of product thus obtained is chromatographed on silica gel. The solvent is evaporated from the fractions obtained using a 97.5:2.5 mixture of DCM and methanol as eluent and evaporated to dryness in vacuo. Thus, 265 mg of the desired product are obtained, with an Rf value of 0.30 (eluent: DCM / methanol 95:5). Step B: 7-[6-Deoxy-5-C-methyl-4-O-methyl-aL-lyxo-hexopyranosyl)oxy]-3-(ethoxyacetyl)-4-hydroxy-8-methyl-2H-1-benzopyran-2-one-(5-methyl-1H-pyrrole-2-carboxylic acid-3)-ester To a solution of 245 mg of the product prepared in step A) and 10 ml of methanol, 50 mg of PTSA are added, the mixture is stirred at ambient temperature for 5 hours, then diluted with a mixture of ethyl acetate and hexane; the mixture is washed with dilute sodium bicarbonate solution, the organic phase is washed first with water, then with concentrated brine, and after drying, it is evaporated to dryness. The 163 mg of product thus obtained is chromatographed on silica gel, using a 92:8 mixture of DCM and methanol as eluent, thus obtaining 116 mg of the desired product, i.e. the title compound of Example 2; Rf=0.20 (chloroform / methanol 94:6). 'H-NMR spectrum (300 MHz, DMSO-d6, δ ppm): 1.07 (s, 3H), 1.17 (t, 3H, J=7.0 Hz), 1.30 (s, 3H), 2.22 (s, 3H), 2.26 (s, 3H), 3.56 (q, 2H, J=7.0 Hz), 3.66 (d, 1H, J=10.0 Hz), 4.18 (m, 1H), 4.71 (broad s, 2H), 5.48 (dd, 1H, J=3.0 and 10.0 Hz), 5.66 (broad s, 1H), 5.72 (d, 1H, J=5.0 Hz), 5.93 (m, 1H), 6.78 (m, 1H), 7.21 (d, 1H, J=9.0 Hz), 7.90 (dd, 1H, J=9.0 Hz), 11.65 (broad s, 1H), 15.25 (very broad, 1H). Example 3 (Z) Preparation of 7-[(6-Deoxy-5-C-methyl-4-O-methyl-α-L-lyxo-hexopyranosyl)-oxy]-4-hydroxy-3-[1-hydroxy-2(2-pyridinyl)-ethenyl]-8-methyl-2H-1-benzopyran-2-one-(5methyl-1H-pyrrole-2-carboxylic acid-3)-ester HU 222 787 Bl Step A: (Z) 7-{[6-Deoxy-5-C-methyl-4-O-methyl-2O-(tetrahydro-2H-pyran-2-yl)-aL-lyxohexopyranosyl]oxy}-4-hydroxy-3-[1-hydroxy-2-(2-pyridinyl)-ethenyl]-8-methyl-2H1-benzopyran-2-one-(5-methyl-1H-pyrrole2-carboxylic acid-3)-ester The procedure is carried out similarly to step A) of the previous example: starting from 300 mg of the product prepared in step C) of example 1 and 100 mg of 2-pyridinylacetic acid hydrochloride, 135 mg of the desired product is obtained, whose Rf value is 0.64 (DKM / THF 50:50); Rf=0.45 (DKM / methanol 94:6). Step B: (Z) 7-[(6-Deoxy-5-C-methyl-4-O-methyl-L-lyxo-hexopyranosyl)-oxy]-4-hydroxy-3- [1-hydroxy-2-(2-pyridinyl)-ethenyl]-8-methyl-2H-1-benzopyran-2-one-(5-methyl-1Hpyrrole-2-carboxylic acid-3)-ester The same procedure as in the last step of Example 1 was followed; starting from 135 mg of the product obtained in Step A), 29 mg of the desired product, i.e. the title compound of Example 3, were obtained. • H-NMR spectrum (300 MHz, DMSO-d6, δ ppm): 1.09 (s, 3H), 1.30 (s, 3H), 2.23 (s, 3H), 2.25 (s, 3H), 3.48 (s, 3H), 3.66 (d, 1H, J=10.0 Hz), 4.16 (m, 1H), 5.49 (dd, 1H, J=3.0 and 10.0 Hz), 5.60 (d, 1H, J=2.0 Hz), 5.93 (m, 1H), 6.78 (m, 1H), 6.82 (s, 1H), 7.08 (dd, 1H, J=5.0 and 7.5 Hz), 7.12 (d, 1H, J=9.0 Hz), 7.62 (ld, 1H, J=8.0 Hz), 7.80 (d, 1H, J=9.0 Hz), 7.94 (dd, 1H, J=7.5 and 8 Hz), 8.16 (d, 1H, J=5 Hz), 11.65 (broad s, 1H), 13.04 (m, 1H), 13.81 (m, 1H). Production example 3 Preparation of 7-Hydroxy-8-methyl-2-oxo-4-(benzyloxy)-2H-1-benzopyran-3-carboxylic acid ethyl ester Step A: 4-Hydroxy-8-methyl-2-oxo-7-[(tetrahydro-2H-pyran-2-yl)oxy]-2H-1-benzopyran-3-carboxylic acid ethyl ester To a mixture of 1.2 liters of DKM and 120.65 g of the product obtained in step B of Preparation Example 2, 106.7 g of DMAP are added, the resulting mixture is cooled in an ice bath, and 57.1 ml of ethyl chloroformate are added over 50 minutes at a temperature below 5 °C. A further 26.6 g of DMAP and 21 ml of ethyl chloroformate are added. The reaction mixture is adjusted to pH 6 by adding 1 liter of 1 molar aqueous sodium dihydrogen phosphate solution and then sodium dihydrogen phosphate in powder form. The aqueous phase is extracted with DKM, the combined organic phase is washed with 1 N hydrochloric acid solution, then washed with water, decanted and evaporated to dryness after drying and filtration. Thus, 144.63 g of the desired product is obtained. Step B: 8-Methyl-2-oxo-4-(benzyloxy)-7-[(tetrahydro-2H-pyran-2-yl)oxy]-2H-1-benzopyran-3-carboxylic acid ethyl ester To a solution of 1.2 liters of DCM, 120.90 g of the product prepared in the previous step, 54 ml of benzyl alcohol and 109.1 g of triphenylphosphine at 0 °C over 90 minutes, 76 ml of diethylazodicarboxylate are added. The mixture is filtered and the filtrate is poured into 500 ml of 1 molar sodium dihydrogen phosphate solution. The mixture is extracted with DCM, washed, dried and, after filtration, evaporated to dryness. 355.5 g of product are obtained, which are taken up in DCM and the reaction mixture is kept in a refrigerator overnight. After filtration, the filtrate obtained is evaporated and dried. The 324.7 g of product thus obtained are taken up in diisopropyl ether, stirred, after filtration the insoluble product is washed with ether and the filtrate is dried. Evaporation in vacuo gave 251 g of crude product, which was chromatographed on silica gel. The elution was started with DCM and continued with a 90:10 mixture of DCM and ethyl acetate to give the desired product. Step C: 7-Hydroxy-8-methyl-2-oxo-4-(benzyloxy)2H-1-benzopyran-3-carboxylic acid ethyl ester To a solution of the product prepared in the previous step and 2 liters of THF, 1 liter of 1 N hydrochloric acid solution is added, and the mixture is stirred for 4 hours at ambient temperature, then 2 liters of DCM are added, and the mixture thus obtained is washed first with 10% aqueous sodium bicarbonate solution and then with concentrated aqueous brine. The organic phase is dried, evaporated to dryness, the product is triturated to a paste in diethyl ether, separated and, after washing, dried in vacuo. Thus, the desired product, i.e. the title compound of Preparation Example 3, is obtained in a yield of 59.8 g, having an Rf value of 0.15 (DCM / ethyl acetate 95:5). •H-NMR spectrum in dimethyl sulfoxide (abbreviated: DMSO): H at 6-position 6.89 ppm OH group H 10.72 (s) ppm Methoxy group H 5.29 (s) ppm CH2CH3H 4.33 (a) CH2CH3H 1.29 (t) 8-position methyl group H 2.16 (s) ppm. Example 4 (Z) Preparation of 7-[(6-Deoxy-5-C-methyl-4-O-methyl-a.-L-lyxohexopyranosyl)oxy]-4-hydroxy-8-methyl-2-oxo-2H1-benzopyran-3-carboxylic acid ethyl ester-(5-methyl-1H-pyrrole-2-carboxylic acid-3)-ester Step A: (Z) 7-[(6-Deoxy-5-C-methyl-4-O-methyl-L-lyxohexopyranosyl)oxy]-8-methyl-2oxy-4-(benzyloxy)-2H-1-benzopyran-3carboxylic acid ethyl ester-(5-methyl-1H-pyrrole-2-carboxylic acid-3')-ester The same procedure as in step A) of Example 1 was followed, starting from the products prepared in Preparation Examples 1 and 3, to obtain the desired product, which had an Rf value of 0.55 (diethyl ether / hexane 1:2). Step B: (Z) 7-[(6-Deoxy-5-C-methyl-4-O-methyl-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-carboxylic acid ethyl ester-(5-methyl-1H-pyrrole-2-carboxylic acid-3)-ester To a solution of 330 mg of the product obtained in step A) and 10 ml of absolute ethanol, 35 mg of 10% palladium-on-carbon catalyst were added and the mixture was shaken for 5 hours under a slight pressure of hydrogen at ambient temperature. After filtration, the ethanol was evaporated to dryness and the residue was sonicated in the presence of diisopropyl ether. After separation and drying, the desired HU 222 787 B1 product, i.e. the title compound of Example 4 It was absorbed in a yield of 189.4 mg; Rf=0.43 (DKM / methanol 91:9). • H-NMR spectrum (300 MHz, DMSO-d^, δ ppm): 1.07 (s, 3H), 1.30 (s, 3H), 1.32 (t, 3H, J=7.0 Hz), 2.22 (s, 3H), 2.25 (s, 3H), 3.48 (s, 3H), 3.66 (d, 1H, J=10.0 Hz), 4.18 (broad s, 1H), 4.37 (q, 2H, J=7.0 Hz), 5.48 (dd, 1H, J=3.0 and 10.0 Hz), 5.66 (d, 1H, J=2.0 Hz), 5.73 (broad s, 1H), 5.93 (t, 1H, J=3 Hz), 6.78 (t, 1H, J=3.0 Hz), 7.23 (d, 1H H, J=9.0 Hz), 7.86 (d, 1H, J=9.0 Hz), 11.66 (broad s, 1H). Example 5 Preparation of 3-Acetyl-7-[(6-deoxy-5-C-methyl-4-O-methyl-aL-lyxo-hexopyranosyl)-oxy]-4-hydroxy-8-methyl-2H-l-benzopyran-2-one-(5-methyl-lH-pyrrole-2-carboxylic acid-3)-ester Step A: 7-[(6-Deoxy-5-C-methyl-4-O-methyl-a,L-lyxohexopyranosyl)oxy]-8-methyl-2oxo-4-(benzyloxy)-1H-1-benzopyran-3-carboxylic acid ethyl ester g Product prepared in Step C of Example 1, 746 mg To a solution of 4-(dimethylamino)pyridine, 433 mg of N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride and 20 ml of DCM, 136 µl of acetic acid were added and the reaction mixture was shaken for 16 hours at ambient temperature and then diluted with DCM. The resulting solution was washed with 10% aqueous sodium hydrogen sulfate, dried, filtered and evaporated to dryness. The reaction mixture was triturated thoroughly with a 2:1 mixture of hexane and ethyl acetate, and after separation and drying, 634 mg of the desired product was obtained, with an Rp value of 0.63 (DCM / methanol 94:6). Step B: 3-Acetyl-7-[(6-deoxy-5-C-methyl-4-O-methyl-a.-L-lyxo-hexopyranosyl)-oxy]-4-hydroxy-8-methyl-2H-1-benzopyran-2-one-(5methyl-1H-pyrrole-2-carboxylic acid-3)-ester To a solution of 568.4 mg of the product obtained in step A) in 20 ml of methanol and 15 ml of DCM was added 80 mg of PTSA and the mixture was shaken at ambient temperature for 4 hours, then the reaction mixture was poured into a mixture of DCM and saturated aqueous sodium bicarbonate solution. The aqueous phase was extracted with DCM, the combined organic phase was dried, filtered and evaporated to dryness in vacuo. Thus, the desired product, the title compound of Example 5, was obtained in a yield of 254 mg, with an Rf value of 0.39 (DCM / methanol 94:6). • H-NMR spectrum (300 MHz, DMSO-d6, δ ppm): 1.06 (s, 3H), 1.30 (s, 3H), 2.22 (s, 3H), 2.24 (s, 3H), 2.66 (s, 3H), 3.47 (s, 3H), 3.66 (d, 1H, J=9.5 Hz), 4.18 (broad s, 1H), 5.48 (dd, 1H, J=3 and 9.5 Hz), 5.69 (d, 1H, J=2.5 Hz), 5.75 (d, 1H, J=5 Hz), 5.93 (t, 1H, J=3.0 Hz), 6.79 (t, 1H, J=3.0 Hz), 7.25 (d, 1H, J=8.5 Hz), 7.92 (d, 1H, J=8 Hz), 11.66 (br s, 1H), 15.44 (br s, 1H). Production example 4 Preparation of 7-Hydroxy-8-methyl-2-oxo-4-(benzyloxy)-1H-1-benzopyran-3-carboxylic acid (2-methylpropyl) ester Step A: {8-Methyl-2-oxo-7-[(tetrahydro-2H-pyran2-yl)oxy]-2H-1-benzopyran-4-yl}-(2-methylpropyl)carbonate To a solution of 6.907 g of the product obtained in step B of Preparation Example 2 and 40 ml of THF, 6.96 ml of triethylamine and then 3.57 ml of isobutyl chloroformate were added. The mixture was stirred for 1 hour at ambient temperature, then diluted with THF, washed with 10% aqueous sodium hydrogen sulfate solution, dried and evaporated to dryness. The product was sonicated in the presence of a 2:1 mixture of hexane and ethyl acetate, then separated and dried. Thus, the desired product was obtained in a yield of 7.475 g, the Rr value of which was 0.74 (DKM / methanol 94:6). Step B: 4-Hydroxy-8-methyl-2-oxo-7-[(tetrahydro-2H-pyran-2-yl)oxy]-2H-1-benzopyran-3-carboxylic acid (2-methylpropyl) ester To a solution of 7.30 g of the product obtained in step A) and 50 ml of DCM, 2.37 g of DMAP were added and the mixture was stirred at ambient temperature for 5 hours and then diluted with DCM. The solution was washed with 10% aqueous sodium hydrogen sulfate solution and, after drying, evaporated in vacuo. The product thus obtained was chromatographed on silica gel, eluting with a 1:1 mixture of hexane and ethyl acetate. The solvents were evaporated and the product obtained was dried. Thus, 3.0 g of the desired product was obtained, the Rf value of which was 0.38 (hexane / ethyl acetate 1:1). Step C: 8-Methyl-2-oxo-4-(benzyloxy)-7-[(tetrahydro-2H-pyran-2-yl)oxy]-2H-1-benzopyran-3-carboxylic acid (2-methylpropyl) ester To a mixture of 2.80 g of the product obtained in the previous step, 928 μl of benzyl alcohol and 2.34 g of triphenylphosphine, 1.222 ml of diethyl azodicarboxylate are added at 0 °C, and the mixture is shaken for 2 hours at ambient temperature. At this time, 976 mg of triphenylphosphine and 585 μΐ of diethyl azodicarboxylate are added, and shaking is continued for 2 hours at ambient temperature. After evaporation, the product obtained is chromatographed on silica gel. Using a 2:1 mixture of hexane and ethyl acetate as eluent, then evaporating the solvents from the solutions and drying the product obtained, 2.18 g of the desired product are obtained, whose Rp value is 0.25 (hexane / ethyl acetate 2:1). Step D: 7-Hydroxy-8-methyl-2-oxo-4-(benzyloxy)2H-1-benzopyran-3-carboxylic acid (2-methylpropyl) ester To a solution of 2.00 g of the product obtained in the previous step and 70 ml of THF was added 35 ml of 1 molar aqueous hydrochloric acid. The mixture was shaken at ambient temperature for 7 hours and then diluted with a 1:1 mixture of hexane and ethyl acetate. The phases were separated and the aqueous phase was extracted with a 1:1 mixture of hexane / ethyl acetate. The organic phases were combined, washed with a 1 molar solution of sodium dihydrogen phosphate, dried and evaporated to dryness. The residue was thoroughly treated with ultrasound in a 4:1 mixture of hexane and ethyl acetate, and the product obtained after separation was dried to give 1.27 g of the desired compound, i.e. the title compound of Preparation Example 4. Rf=0.64 (DKM / methanol 94:6). HU 222 787 B1 Example 6 Preparation of 7-[(6-Deoxy-5-C-methyl-4-O-methyl-aL-lyxo-hexopyranosyl)-oxy]-4-hydroxy-8-methyl-2-oxo-2H1-benzopyran-3-carboxylic acid (2-methyl-propyl)-ester-(5methyl-1H-pyrrole-2-carboxylic acid-3 [-ester Step A: 7-[(6-Deoxy-5-C-methyl-4-O-methyl-(1L-lyxo-hexopyranosyl)oxy]-8-methyl-2oxo-4-(benzyloxy)-2H-1-benzopyran-3-carboxylic acid (2-methylpropyl) ester-(5-methyl-1H-pyrrole-2-carboxylic acid-3) ester The procedure described in step A) of Example 1 is followed, starting from the product of Preparation Example 4 and the product of Preparation Example 1, to obtain the desired product. Step B: 7-[(6-Deoxy-5-C-methyl-4-O-methyl-aL-lyxo-hexopyranosyl)-oxy]-4-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-carboxylic acid-(2-methyl-propyl)-ester-(5-methyl-1Hpyrrole-2-carboxylic acid-3[-ester To a solution of 430 mg of the product obtained in step A), 4 ml of ethanol and 3 ml of THF, 50 mg of 10% palladium-on-carbon catalyst were added, the mixture was shaken under hydrogen gas atmosphere for 3 hours, then filtered. The solvent was evaporated in vacuo, the residue was treated with ultrasound in the presence of diisopropyl ether, then the product was isolated and dried, and thus 279 mg of the desired product, i.e. the title compound of Example 6, was obtained. 'H-NMR spectrum (300 MHz, DMSO-d6, δ ppm): 0.94 (d, 6H, J=6.5 Hz), 1.10 (s, 3H), 1.29 (s, 3H), 1.92 (m, 2H), 2.17 (s, 3H), 2.25 (s, 3H), 3.47 (s, 3H), 3.64 (d, 1H, J=10.0 Hz), 3.89 (d, 2H, J=6.5 Hz), 4.15 (m, 1H), 5.48 (dd, 1H, J=3.0 and 10.0 Hz), 5.54 (broad s, 1H), 5.64 (d, 1H, J=5.0 Hz), 5.92 (m, 1H), 6.77 (m, 1H), 6.99 (d, 1H, J=9.0 Hz), 7.76 (d, 1H, J=9.0 Hz), 11.66 (broad s, 1H). Example 7 Preparation of 7-[3-O-(Aminocarbonyl)-6-deoxy-5-C-methyl-4-O-methyl-a.-L-lyxohexopyranosyl)oxy]-4-hydroxy-8-methyl-2H1-benzopyran-3-carboxylic acid (2-methylpropyl) ester Step A: 7-[(6-Deoxy-5-C-methyl-4-O-methyl-aL-lyxohexopyranosyl)oxy]-8-methyl-2oxo-4-(benzyloxy)-2H-1-benzopyran-3carboxylic acid (2-methylpropyl) ester The procedure is as in Example 1, step A), starting with 6-deoxy-5-C-methyl-4-O-methyl-α-L-lixohexopyranose and 7-hydroxy-8-methyl-2-oxo-4-(benzyloxy)-2H-1-benzopyran-3-carboxylic acid (2-methylpropyl) ester, to give the desired product with an Rf value of 0.22 (hexane / ethyl acetate 1:2). Step B: 7-[(2,3-O-Carbonyl-6-deoxy-5-C-methyl-4-O-methyl-a.-L-lyxohexopyranosyl)oxy]-8-methyl-2-oxo-4-(benzyloxy)-2H1-benzopyran-3-carboxylic acid (2-methylpropyl) ester A mixture of 700 mg of the product prepared in step A), 408 mg of carbonyldiimidazole and 10 ml of THF is heated to boiling point under reflux and boiled for 30 minutes under reflux, then diluted with 50 ml of a 1:2 hexane-ethyl acetate mixture. The mixture is washed with a 1 molar aqueous sodium dihydrogen phosphate solution, then dried and, after filtration, evaporated to dryness. The product thus obtained is chromatographed; using a 1:1 hexane-ethyl acetate mixture as eluent, 530 mg of the desired product are obtained, whose Rf value is 0.63 (hexane / ethyl acetate 1:2). Step C): A mixture of 7-[(2,3-O-Carbonyl-6-deoxy-5-C-methyl-4-O-methyl-a.-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-2-oxo-2H1-benzopyran-3-carboxylic acid-(2-methyl-propyl)-ester ml ethanol, 2 ml THF and 300 mg of the product prepared in the previous step - after adding the catalyst, is shaken at ambient temperature in a hydrogen atmosphere for 1 hour, then filtered, the catalyst is washed with THF, and the product thus obtained is evaporated to dryness, thoroughly processed by ultrasonication in the presence of diethyl ether, then separated and dried. Thus, 180 mg of product is obtained, the Rr value of which is 0.52 (hexane / ethyl acetate 1:1). Step D: 7-[3-O-(Aminocarbonyl)-6-deoxy-5-methyl-4-O-methyl-[alpha]-L-lyxohexopyranosyl]oxy]-4-hydroxy-8-methyl-2H-1-benzopyran-3-carboxylic acid (2-methylpropyl[ester To a solution of 506 mg of the product obtained in step C) and 3 ml of THF, 15 ml of liquid ammonia were added and the ammonia was allowed to evaporate. The residue was taken up in a 5:3:2 mixture of THF-ethyl acetate-hexane and washed with 10% aqueous sodium hydrogen sulfate solution, dried and evaporated to dryness. The residue thus obtained was thoroughly sonicated in the presence of diisopropyl ether. After isolation and drying, 310 mg of the desired product, i.e. the title compound of Example 7, were obtained, the Rf value of which was 0.25 (DKM / methanol 91:9). H-NMR spectrum (400 MHz, DMSO-d6, δ ppm): 0.98 (d, 6H, J=6.5 Hz), 1.02 (s, 3H), 1.27 (s, 3H), 2.01 (m, 1H), 2.18 (s, 3H), 3.46 (s, 3H), 3.47 (d, 1H, J=10.0 Hz), 3.47 (s, 1H), 4.08 (ti, 1H, J=2.5 Hz), 4.11 (d, 2H, J=6.5 Hz), 5.14 (dd, 1H, J=5 and 10.3 Hz), 5.57 (d, 1H, J=2.5 Hz), 5.63 (s, 1H), 6.61 (broad s, 2H), 7.19 (d, 1H, J=9 Hz), 7.84 (d, 1H, J=9 Hz). Preparation Example 5 Preparation of (E)-3-{1-[(2-Bromoethoxy)imino]ethyl}-7-hydroxy-8methyl-4-(2-propenyloxy)-2H-1-benzopyran-2-one Step A: (E)-3-{1-[(2-Bromoethoxy)imino]ethyl}-4-hydroxy-8-methyl-7-tetrahydro-2H-pyran-2-yl)oxy]-2H-1-benzopyran-2-one A mixture of 3.183 g of the product prepared in step A of Preparation Example 7, 4.418 g of O-(bromoethyl)hydroxylamine hydrobromide and 2.94 g of potassium acetate in 20 ml of ethanol was refluxed for 1 hour, then the ethanol was evaporated, and the residue was dissolved in 100 ml of DCM in the presence of 50 ml of aqueous sodium dihydrogen phosphate solution. HU 222 787 Bl. After separation of the phases, the DCM solution is dried, evaporated and the residue is chromatographed on silica gel. The elution is carried out with a 2:1 mixture of hexane and ethyl acetate, then the solvents are evaporated and the resulting product is dried, thus obtaining 2.00 g of product, the Rr value of which is 0.57 (DCM / methanol 94:6). Step B: (E)-3-{1-[(2-Bromoethoxy)imino]ethyl}-7-hydroxy-8-methyl-4-(2-propenyloxy)-2Hpyran-2-yl)oxy]-2H-1-benzopyran-2-one To a solution of 1.96 g of the product obtained in the previous step, 360 μΐ allyl alcohol, 1.401 g triphenylphosphine and 30 ml of DKM at 0 °C was added 914 μΐ diethyl azodicarboxylate. The mixture was stirred at ambient temperature for 2 hours, then 180 μΐ allyl alcohol, 700 mg triphenylphosphine and 457 μΐ diethyl azodicarboxylate were added at 0 °C. The mixture was stirred again at ambient temperature for 2 hours, then evaporated and chromatographed on silica gel. Elution was carried out with a 4:1 mixture of hexane and ethyl acetate to give 2.0 g of product, which was poured into 40 ml of THF, 20 ml of 1 molar aqueous hydrochloric acid was added and stirred at ambient temperature for 2 hours. Then, it is diluted with 30 ml of a 1:2 hexane-ethyl acetate mixture, the organic phases are combined, washed with an aqueous solution of sodium dihydrogen phosphate, then dried, filtered, and evaporated. The product is thoroughly sonicated in the presence of a 3:1 mixture of hexane and ethyl acetate, then filtered and dried.Thus, 1.17 g of the desired product, i.e. the title compound of Example 7, is obtained, having an Rf value of 0.28 (hexane / ethyl acetate 4:1). Example 8 Preparation of (E)-3-{1-[(2-Bromoethoxy)imino]ethyl}-7-[(6-deoxy-5C-methyl-4-O-methyl-α-L-lyxohexopyranosyl)oxy]-4-hydroxy-8-methyl-2H-1-benzopyran-2-one-(5-methyl-1H-pyrrole-2-carboxylic acid-3)-ester Step A: (E)-7-[(6-Deoxy-5-C-methyl-4-O-methyl-L-lyxo-hexopyranosyl)oxy]-8-methyl-4(2-propenyloxy)-2H-1-benzopyran-2-one(5-methyl-1H-pyrrole-2-carboxylic acid-3')-ester 1.12 g of the product obtained in step A) of Preparation Example 5, 1.015 g of the product obtained in Preparation Example 1, 890 mg of diphenylphosphine and 15 ml of DKM are added dropwise to a mixture of 580 μΐ diethyl azodicarboxylate at 0 °C, the reaction mixture is stirred for 2 hours at ambient temperature, then 450 mg of triphenylphosphine and 295 μΐ diethyl azodicarboxylate are added. Stirring is continued for another 1 hour, then another 300 mg of triphenylphosphine and 196 μΐ diethyl azodicarboxylate are added. At this time, stirring is continued for 1 hour, then evaporation is carried out, the residue is chromatographed twice on silica gel. Elution is carried out with a 2:1 mixture of hexane and ethyl acetate. The solvents are evaporated and the residue is dried. 862 mg of the desired product are obtained. Step B: (E)-3-{1-[(2-Bromoethoxy)imino]ethyl}-7[(6-deoxy-5-C-methyl-4-O-methyl-aL-lyxohexopyranosyl)oxy]-4-hydroxy-8methyl-2H-1-benzopyran-2-one-(5-methyllH-pyrrole-2-carboxylic acid-3)-ester The procedure described in step C) of Example 1, using the product of the previous step as the starting material, gives the desired product, i.e. the title compound of Example 8. Rf=0.28 (diethyl ether / hexane 2:1). H-NMR spectrum (300 MHz, DMSO-d6, δ ppm): 1.08 (s, 3H), 1.30 (s, 3H), 2.24 (s, 3H), 2.25 (s, 3H), 2.28 (s, 3H), 3.47 (s, 3H), 3.65 (d, 1H, J=9.5 Hz), 3.74 (t, 2H, J=5.5 Hz), 4.17 (m, 1H), 4.48 (t, 2H, J=5.5 Hz), 5.48 (dd, 1H, J=3 and 9.5 Hz), 5.64 (d, 1H, J=2.5 Hz), 5.71 (m, 1H), 5.93 (m, 1H), 6.78 (m, 1H), 7.21 (d, 1H, J=9.0 Hz), 7.81 (d, 1H, J=9.0 Hz), 11.66 (broad s, 1H), 13.14 (broad m, 1H). Example 9 (E) Preparation of 7-[(6-Deoxy-5-C-methyl-4-O-methyl-α-L-lyxo-hexopyranosyl)-oxy]-3-[1-(2-dimethylaminoethoxy)-imino]-ethyl-4-hydroxy-8-methyl-2H1-benzopyran-2-one-(5-methyl-1H-pyrrole-2-carboxylic acid 3')-ester To a solution of 150 mg of the final product prepared in Example 8 and 2 ml of anhydrous DMF, 10 mg of (tetrabutylammonium) iodide and then 53 mg of 4-(dimethylamino)pyridine and 1 ml of DMF were added. The reaction mixture was stirred at ambient temperature for 4 hours and then poured into a mixture of 50 ml of a 2:2:1 THF-ethyl acetate-hexane mixture and 50 ml of water. The aqueous phase was extracted, the combined organic phase was washed, then dried and evaporated to dryness. The resulting product was thoroughly sonicated in the presence of diisopropyl ether. After isolation and drying, 55 mg of the title compound were obtained, with an R value of 0.10 (DKM / methanol 91:9). 'H-NMR spectrum (300 MHz, DMSO-d6, δ ppm): 1.09 (s, 3H), 1.29 (s, 3H), 2.06 (s, 3H), 2.25 (s, 3H), 2.19 (s, 3H), 2.86 (s, 6H), 3.36 (1,2H), 3.47 (s, 3H), 3.64 (d, 1H, J=9.5 Hz), 4.15 (m, 1H), 4.34 (1, 2H), 5.48 (dd, 1H, J=2.5 and 9.5 Hz), 5.63 (1, 1H), 5.93 (1, 1H), 6.78 (1, 1H), 7.00 (br m, 1H), 7.75 (br m, 1H). Examples 10, 11, 12 and 13 The following compounds were prepared as described in Example 9: (E) 7-[(6-Deoxy-5-C-methyl-4-O-methyl-u.-L-lyxohexopyranosyl)oxy]-4-hydroxy-8-methyl-3-{1-[(2-(4-morpholinyl)ethoxy)imino]ethyl}-2H-1-benzopyran-2-one-(5-methyl1H-pyrrole-2-carboxylic acid-3)-ester, Rf=0.33 (DKM / methanol 91:9). H-NMR spectrum (300 MHz, DMSO-d6, δ ppm): 1.10 (s, 3H), 1.30 (s, 3H), 2.03 (s, 3H), 2.19 (s, 3H), 2.22 (s, 3H), 3.25-3.42 (1, 4H), 3.47 (s, 3H), 3.63 (d, 1H, J=9.5 Hz), 4.02 (1, 6H), 4.14 (broad s, 1H), 4.34 (1, 2H), 5.48 (dd, 1H, J=3 and 9.5 Hz), 5.54 (d, 1H, J=2 H2), 5.64 (d, 1H, J=4.5 Hz), 5.93 (t, 1H, J=3.0 Hz), 6.77 (t, 1H, J=3.0 Hz), 7.03 (d, 1H, J=8.5 Hz), 7.75 (d, 1H, J=8.5 Hz), 11.66 (broad s, 1H). (E) 7-[(6-deoxy-5-C-methyl-4-O-methyl-a.-L-lyxohexopyranosyl)oxy]-4-hydroxy-3-{1-[(2-(4-hydroxy-1-piper HU 222 787 B1 dinyl)-ethoxy)-imino]-ethyl}-8-methyl-2H-1-benzopyran-2-one-(5-methyl-1H-pyrrole-2-carboxylic acid-3-ester, with an R value of 0.50 (DKM / methanol 94:6). 'H-NMR spectrum (300 MHz, DMSO-d6, δ ppm): 1.10 (s, 3H), 1.30 (s, 3H), 1.70-2.25 (m, 4H), 2.02 (s, 3H), 2.19 (s, 3H), 2.24 (s, 3H), 3.34 (m, 6H), 3.47 (s, 3H), 3.63 (d, 1H, J=9.5 Hz), 3.87 (broad s, 1H), 4.13 (m, 1H), 4.34 (broad s, 2H), 5.00 (s, 1H), 5.48 (dd, 1H, J=3.0 and 9.5 Hz), 5.53 (d, 1H, J=2 Hz), 5.63 (d, 1H, J=5.0 Hz), 5.92 (t, 1H, J=3.0 Hz), 6.78 (t, 1H, J=3.0 Hz), 6.98 (d, 1H, J=9.0 Hz), 7.71 (d, 1H, J=9.0 Hz), 11.66 (broad s, 1H). (E) 7-[(6-Deoxy-5-C-methyl-4-O-methyl-a.-L-lyxo-hexopyranosyl)-oxy]-4-hydroxy-3-{1-[[(2-(1H-imidazol-2-yl)thio / ethoxy]-imino]-ethyl}-8-methyl-2H-1-benzopyran-2-one(5-methyl-1H-pyrrole-2-carboxylic acid-3 / ester, Rf=0.20 (DKM / methanol 94:6). H-NMR spectrum (300 MHz, DMSO-d6, δ ppm): 1.09 (s, 3H), 1.30 (s, 3H) 2.23 (s, 3H), 2.25 (s, 3H), 3.38 (m, 2H), 3.48 (s, 3H), 3.66 (d, 1H, J=9.5 Hz), 4.17 (dd, 1H, J=2.0 es 3.0 Hz), 4.37 (t, 2H, J=5.5 Hz), 5.48 (dd, 1H, J=3.0 es 9.5 Hz), 5.62 (d, 1H, J=2 Hz), 5.93 (t, 1H, J=3.0 Hz), 6.78 (t, 1H, J=3.0 Hz), 7.16 (d, 1H, J=9.0 Hz), 7.21 (s, 2H), 7.82 (d, 1H, J=9.0 Hz), 11.66 (s, 1H). (E) 7-[(6-dezoxi-5-C-metil-4-O-metil-aL-lixo-hexopyranozil)-oxi]-4-hidroxi-8-metil-3-{l-[(2-(lH-) l,2,4-triazol-l-il)-etoxi)-imino]-etil}-2H-l-benzopirán-2-on-(5metil-lH-pirrol-2-karbonsav-3 / észter, Rf=0,36 (DKM / metanol 91:9). 'H-NMR-spektrum (300 MHz, DMSO-d^,, δ ppm): 1.07 (s, 3H), 1.30 (s, 3H), 2.14 (s, 3H), 2.25 (s, 3H), 3.47 (s, 3H), 3.66 (d, 1H, J=9.5 Hz), 4.17 (s, 1H), 4.51 (m, 4H), 5.48 (dd, 1H, J=2.5 és 9.5 Hz), 5.64 (d, 1H, J=2 Hz), 5.72 (1, 1H), 5.93 (széles s, 1H), 6.78 (t, 1H, J=3.0 Hz), 7.21 (d, 1H, J=9.0 Hz), 7.81 (d, 1H, J=9.0 Hz), 8.01 (s, 1H), 8.54 (s, 1H), 11.66 (1.1H). Preparation Example 6 (E) Preparation of 3-[2-Ethoxy-1-(methoxyimino / ethyl]-7-hydroxy-8-methyl-4-(2-propenyloxy)-2H-1-benzopyran-2-one Step A: (E) 3-(Ethoxyacetyl / 4-hydroxy-8-methyl-7[(tetrahydro-2H-pyran-2-yl / oxy]-2H-benzopyran-2-one 2.21 ml of ethoxyacetic acid were added to a solution of 5.00 g of 4-hydroxy-8-methyl-7-[(tetrahydro-2H-1-pyran-2-yl)oxy]-2H-1-benzopyran-2-one, 7.30 g of 4-(dimethylamino)pyridine and 3.816 g of N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride and the mixture was stirred for 16 hours at ambient temperature. At this time, it was diluted with DCM, washed with aqueous sodium dihydrogen phosphate solution and then with brine. The solution was dried over anhydrous magnesium sulfate, filtered and evaporated to dryness. The product thus obtained was thoroughly triturated with a 4:1 mixture of hexane and ethyl acetate and the resulting material was isolated and dried. Thus, 5.40 g of the desired product was obtained. Step B): (E) 3-[2-Ethoxy-1-(methoxyimino)ethyl]-4-hydroxy-8-methyl-7-[(tetrahydro-2H-pyran-2-yl / oxy]-2H-1-benzopyran-2-one g of the product obtained in the previous step, 922 mg of methoxyamine hydrochloride, 1.62 g of potassium acetate and 20 ml of ethanol are boiled under reflux for 2 hours, then the ethanol is completely evaporated. The product thus obtained is chromatographed on silica gel, elution is first carried out with a 1:1 hexane-ethyl acetate mixture and then with a 94:6 DCM-methanol mixture. After evaporation of the solvents, the product obtained is dried, thus obtaining the desired product in a yield of 1.014 g, Rr value 0.22 (DCM / methanol 94:6). Step C): (E) 3-[2-Ethoxy-1-(methoxyimino)ethyl]-8methyl-4-(2-propenyloxy)-7-[(tetrahydro2H-pyran-2-yl)oxy]-2H-1-benzopyran-2one g of the product prepared in the previous step, 208 µl of allyl alcohol, 804 mg of triphenylphosphine and 15 ml of DKM are added with 534 µl of diethyl azodicarboxylate, the reaction mixture is stirred for 2 hours at ambient temperature, then 402 mg of triphenylphosphine, 104 µl of allyl alcohol and 267 µl of diethyl azodicarboxylate are added. Stirring is continued for 2 hours at ambient temperature, then the mixture is evaporated in vacuo and the residue is chromatographed on silica gel. Elution was carried out with a 2:1 mixture of hexane and ethyl acetate, and the product obtained after evaporation of the solvents was dried, yielding 672 mg of the desired product, Rf value 0.60 (hexane / ethyl acetate 1:2). Step D: (E) 3-[2-Ethoxy-1-(methoxyimino)ethyl]-7-hydroxy-8-methyl-4-(2-propenyloxy)-2H1-benzopyran-2-one To a solution of 650 mg of the product obtained in the previous step and 12 ml of THF, 12 ml of aqueous hydrochloric acid were added, and the mixture was stirred for 6 hours at ambient temperature, then diluted with 50 ml of 1:2 hexane-ethyl acetate. The mixture was extracted with 1:2 hexane-ethyl acetate, the organic phases were combined, washed with sodium dihydrogen phosphate solution, dried, and evaporated to dryness after filtration. The residue was thoroughly triturated by ultrasound in the presence of 3:1 hexane-ethyl acetate, separated, and dried, and thus the desired product, i.e. the title compound of Preparation Example 6, was obtained in a yield of 410 mg; Rf value 0.50 (hexane / ethyl acetate 1:1). Example 14 Preparation of 7-[(6-Deoxy-5-C-methyl-4-O-methyl-aL-lyxo-hexopyranosyl / oxy]-3-[2-ethoxy-1-(methoxyimino / ethyl]-4-hydroxy-8-methyl-2H-1-benzopyran-2-one-(5-methyl-1H-pyrrole-2-carboxylic acid-3' / ester Step A: 7-[(6-Deoxy-5-C-methyl-4-O-methyl-aL-lyxo-hexopyranosyl)-oxy]-3-[2-ethoxy-l-(methoxyimino / ethyl]-8-methyl-4-(2-propenyloxy)-2H-l-benzopyran-2-one-(5-methyllH-pyrrole-2-carboxylic acid-3 / ester The procedure described in Step 1 of Example 1 was followed, using the product of Preparation Example 1 and the product of Preparation Example 6 as starting materials, to obtain the desired product with an Rf value of 0.41 (hexane / ethyl acetate 1:1). HU 222 787 Bl Step B: 7-[(6-Deoxy-5-C-methyl-4-O-methyl-aL-lyxo-hexopyranosyl)-oxy]-3-[2-ethoxy-l(methoxyimino)-ethyl]-4-hydroxy-8-methyl2H-l-benzopyran-2-one-(5-methyl-lH-pyrrole-2-carboxylic acid-3[-ester To a solution containing 170 mg of the product prepared in the previous step, 31 mg of palladium tetrakis(triphenylphosphine), 180 μΐ diisopropylamine and 5 ml of THF are added. The mixture is stirred at 0 °C for 20 minutes, then the reaction mixture is poured into 25 ml of 10% sodium hydrogen sulfate solution and 50 ml of 1:4 hexane-ethyl acetate mixture are added. The organic phase is washed, dried and, after filtration, evaporated to dryness. The residue is chromatographed on silica gel, eluting with DCM containing 5% methanol. The residue obtained after evaporation of the solvents is thoroughly triturated with diethyl ether under ultrasonic treatment and dried after separation. Thus, the desired product, i.e. the title compound of Example 14, was obtained in a yield of 72 mg, with an Rf value of 0.41 (hexane / ethyl acetate 1:1). • H-NMR spectrum (300 MHz, DMSO-d6, δ ppm): 0.96 (t, J=7.0 Hz), 1.03 (t, J=7.0 Hz), 1.08 (s), 1.29 (s), 2.20-2.30 (m), 3.30 (m), 3.47 (s), 3.50 (m), 3.65 (d, J=10 Hz), 3.76 (s), 3.87 (s), 4.16 (m), 4.23 (s), 4.42 (s), 5.48 (dd, J=3 and 10 Hz), 5.60 (m), 5.68 (d, J = 5.0 Hz), 5.93 (m), 6.78 (m), 7.10 (d, J=9.0 Hz), 7.16 (d, J=9.0 Hz), 7.77 (d, J=9.0 Hz), 11.65 (wide s). Preparation Example 7 (E) Preparation of 7-Hydroxy-3-[1-(methoxyimino)ethyl]-8-methyl-4-(2-propenyloxy)-2H-1-benzopyran-2-one Step A: 3-Acetyl-4-hydroxy-8-methyl-7-[(tetrahydro-2H-pyran-2-yl)oxy]-2H-1-benzopyran-2-one To a solution of 10.00 g of the product prepared in step B) of Preparation Example 2, 14.59 g of 4-(dimethylamino)pyridine and 7.63 g of N(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride, 2.39 ml of acetic acid were added, the mixture was stirred at room temperature for 5 hours, then 4.86 g of 4(dimethylamino)pyridine and 3.82 g of N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride were added again to the mixture, and stirring was continued for 16 hours. The mixture was then diluted with DCM, washed with 10% aqueous sodium hydrogen sulfate, dried, filtered and evaporated to dryness. The residue was thoroughly sonicated in the presence of a 2:1 mixture of hexane and ethyl acetate, and the product obtained after separation was dried. Thus, 10.04 g of the desired product were obtained, the Rf value of which was 0.79 (DCM / methanol 95:5). Step B: (E) 4-Hydroxy-3-[1-(methoxyimino)ethyl]8-methyl-7-[(tetrahydro-2H-pyran-2-yl)oxy]-2H-1-benzopyran-2-one A mixture of 1.7 g of the product prepared in the previous step, 892 mg of methoxyamine hydrochloride, 1.151 g of potassium acetate and 20 ml of ethanol is kept at a temperature of 80 °C for 30 minutes, then evaporated to dryness, the residue is taken up in DCM in the presence of water, washed with a 1 molar aqueous solution of sodium dihydrogen phosphate, dried, and after filtration the filtrate is evaporated to dryness. The product obtained is thoroughly mixed with ultrasound in a 4:1 mixture of hexane and ethyl acetate, and the product obtained is dried. thus 1.60 g of the desired product are obtained, with an Rf value of 0.28 (chloroform / methanol 99.5:0.5). Step C: (E) 3-[1-(Methoxyimino)ethyl]-8-methyl-4(2-propenyloxy)-7-[(tetrahydro-2Hpyran-2-yl)oxy]-2H-1-benzopyran-2-one To a mixture of 1.56 g of the product obtained in step B), 366 μΐ allyl alcohol, 1.43 g triphenylphosphine and 15 ml DKM at 0 °C, 937 μΐ diethyl azodicarboxylate are added and the mixture is stirred for 2 hours at ambient temperature, 706 mg of triphenyl phosphine, 183 μΐ allyl alcohol and 468 μΐ diethyl azodicarboxylate are added again, stirring is continued for another 2 hours at ambient temperature, then the reaction mixture is evaporated and chromatographed on silica gel. Elution is carried out with a 4:1 mixture of hexane and ethyl acetate, the solvents are evaporated and the product obtained is dried. Thus, 1.00 g of the desired product is obtained, the Rr value of which is 0.38 (hexane / ethyl acetate 4:1). Step D): (E) 7-Hydroxy-3-[1-(methoxyimino)ethyl]8-methyl-4-(2-propenyloxy)-2H-1-benzopyran-2-one To a solution of the product obtained in step C) and 20 ml of THF, 10 ml of 1 molar aqueous hydrochloric acid solution was added and the mixture was stirred for 7 hours at ambient temperature, then diluted with a 1:1 mixture of hexane and ethyl acetate (50 ml). After separation, the aqueous phase was extracted with a 1:1 mixture of hexane and ethyl acetate, the combined organic phase was washed with a 1 molar sodium dihydrogen phosphate solution, dried, and evaporated to dryness after filtration. The residue was thoroughly triturated with a 4:1 mixture of hexane and ethyl acetate, and the product obtained after separation was dried to give the desired product, i.e. the title compound of Preparation Example 7, in a yield of 770 mg. Example 15 (E) Preparation of 7-[(6-Deoxy-5-C-methyl-4-O-methyl-α-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-3-[1-(methoxyimino)ethyl]-8-methyl-2H-1-benzopyran-2-one-(5-methyllH-pyrrole-2-carboxylic acid-3[-ester Step A: (E) 7-[(6-Deoxy-5-C-methyl-4-O-methyl-L-lyxo-hexopyranosyl)oxy]-3-[1-(methoxyimino)ethyl]-8-methyl-4-(2-propenyloxy)-2H-1-benzopyran-2-one-(5-methyllH-pyrrole-2-carboxylic acid-3[-ester The procedure described in Example 1 is followed, starting with 455 mg of the product obtained in Preparation Example 7 and 539 mg of the product obtained in Preparation Example 1, to obtain the desired product with an Rf value of 0.33 (eluent hexane:ethyl acetate 1:1). Step B: (E) 7-[(6-Deoxy-5-C-methyl-4-O-methyla-L-lyxo-hexopyranosyl)-oxy]-4-hydroxy-3-[1 -(methoxyimino)-ethyl]-8-methyl-2H1-benzopyran-2-one-(5-methyl-1H-pyrrole2-carboxylic acid-3[-ester To a solution of 380 mg of the product prepared in the previous step and 6 ml of THF at 0 °C, 460 μΐ diisopropyl12 HU 222 787 B1 amine, then 75 mg of palladium tetrakis(triphenylphosphine) are added and the mixture is stirred for 20 minutes at 0 °C, then the reaction mixture is poured into a mixture of 10% sodium hydrogen sulfate solution and a 1:1:1 THF / hexane / ethyl acetate mixture. The phases are separated, the aqueous phase is extracted with a 1:1:1 THF / hexane / ethyl acetate mixture, the organic phases are combined, dried, filtered and evaporated to dryness. The residue is thoroughly sonicated in the presence of diisopropyl ether, the product is isolated and dried in vacuo. Thus, 180 mg of the desired product, i.e. the title compound of Example 15, is obtained, the Rj value of which is 0.35 (DKM / methanol 94:6). H-NMR spectrum (300 MHz, DMSO-d6, δ ppm): 1.08 (s, 3H), 1.30 (s, 3H), 2.23 (s, 3H), 2.25 (s, 3H), 2.27 (s, 3H), 3.47 (s, 3H), 3.65 (d, 1H, J=10.0 Hz), 3.95 (s, 3H), 4.17 (m, 1H), 5.48 (dd, 1H, J=3.0 and 10.0 Hz), 5.63 (d, 1H, J=2.5 Hz), 5.70 (d, 1H, J=5.0 Hz), 5.93 (m, 1H), 6.78 (m, 1H), 7.20 (d, 1H, J=9.0 Hz), 7.80 (d, 1H, J=9.0 Hz), 11.65 (broad, s, 1H), 13.69 (ml, 1H). Preparation Example 8 (E) Preparation of 7-Hydroxy-3-[(methoxyimino)methyl]-8-methyl-4-(2-propenyloxy)-2H-1-benzopyran-2-one Step A): 4-Hydroxy-8-methyl-2-oxo-7-[(tetrahydro2H-pyran-2-yl)-oxy]-2H-l-benzopyran-3carboxaldehyde ml DKM, 5.0 g product prepared in step B) of Preparation Example 2, 6.625 g of 4-(dimethylamino)-pyridine and 3.825 g of N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide are added with 700 μΐ formic acid at ambient temperature, then the mixture is stirred for 16 hours, then diluted with DKM, washed with 10% aqueous sodium hydrogen sulfate solution, then washed with 1 molar solution, then dried, and after filtration the solution is evaporated to dryness. The residue is thoroughly triturated by ultrasonication in the presence of diethyl ether, the product is separated and dried. Thus, 4.04 g of the desired product are obtained. Step B: (E) 4-Hydroxy-3-[(methoxyimino)methyl]8-methyl-7-[(tetrahydro-2H-pyran-2-yl)oxy]-2H-1-benzopyran-2-one A mixture of 2.0 g of the product obtained in step A), 1.08 g of methoxyamine hydrochloride, 1.93 g of potassium acetate and 20 ml of ethanol is heated under reflux for 1 hour and then evaporated to dryness. The residue thus obtained is dissolved in a mixture of 100 ml of DCM and 100 ml of water, washed with dilute sodium dihydrogen phosphate solution and dried. The residue obtained after evaporation of the solution is thoroughly triturated by ultrasonication in the presence of diethyl ether, the product is isolated and dried. Thus, 1.90 g of the desired product is obtained. Step C: (E) 3-[(Methoxyimino)methyl]-8-methyl-4(2-propenyloxy)-7-[(tetrahydro-2Hpyran-2-yl)oxy]-2H-1-benzopyran-2-one To a mixture of 1.80 g of the product prepared in the previous step, 441 μΐ allyl alcohol, 1.70 g of triphenylphosphine and 15 ml of DKM at 0 °C, 1.02 ml of diethyl azodicarboxylate is added and the mixture is stirred at ambient temperature for one hour. Then 845 mg of triphenylphosphine, 220 μΐ allyl alcohol and 564 μΐ DEAD are added at 0 °C. Stirring is continued for 2 hours, then the mixture is evaporated in vacuo and the residue is chromatographed on silica gel. A 3:1 mixture of hexane and ethyl acetate is used as eluent. After evaporation of the solvents and drying of the product, the desired product is obtained in a yield of 1.60 g. Step D: (E) 7-Hydroxy-3-[(methoxyimino)methyl]8-methyl-4-(2-propenyloxy)-2H-1-benzopyran-2-one To a solution of 1.60 g of the product obtained in the previous step and 20 ml of THF, 20 ml of 1 molar aqueous hydrochloric acid solution were added, and the mixture was stirred for 6 hours at ambient temperature, then diluted with 30 ml of hexane / ethyl acetate (1:2). After separation, the aqueous phase was extracted with hexane / ethyl acetate (1:2). The combined organic phase was washed with 1 molar sodium dihydrogen phosphate solution, dried, filtered and evaporated to dryness. The residue was sonicated in the presence of 3:1 hexane / ethyl acetate, the product was isolated and dried. Thus, 920 mg of the desired product, i.e. the title compound of Preparation Example 8, was obtained, with an Rf value of 0.47 (hexane / ethyl acetate 1:2). Example 16 (E) Preparation of 7-[(6-Deoxy-5-C-methyl-4-O-methyl-α-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-3-[(methoxyimino)methyl]-2H-1-benzopyran-2-one-(5-methyl-1H-pyrrole-2-carboxylic acid-3')-ester Step A: (E) 7-[(6-Deoxy-5-C-methyl-4-O-methyl-L-lyxo-hexopyranosyl)oxy]-3-[(methoxyimino)methyl]-8-methyl-4-(2-propenyloxy)-2H-1-benzopyran-2-one-(5-methyllH-pyrrole-2-carboxylic acid-3)-ester The procedure described in Example 1 was followed, using as starting materials the products prepared in Preparation Example 8 and Preparation Example 1, to obtain the desired product having an Rp value of 0.34 (hexane / ethyl acetate 1:1). Step B: (E) 7-[(6-Deoxy-5-C-methyl-4-O-methyla-L-lyxo-hexopyranosyl)-oxy]-4-hydroxy-8-methyl-3-[(methoxyimino)-methyl]-2H1-benzopyran-2-one-(5-methyl-1H-pyrrole2-carboxylic acid-3')-ester To a solution of 430 mg of the product prepared in step A), 533 μΐ diisopropylamine and 10 ml of anhydrous THF at 0 °C, 87 mg of palladium tetrakis(triphenylphosphine) are added, the mixture is stirred for 20 minutes at 0 °C, then the reaction mixture is poured into a mixture of 50 ml of aqueous sodium hydrogen sulfate solution and 50 ml of a 1:2 hexane-ethyl acetate mixture. After washing, the solution is dried and, after filtration, evaporated to dryness. The residue is chromatographed on silica gel, using a 95:5 mixture of DCM and methanol as eluent. The residue obtained after evaporation of the solvents is treated with ultrasound in the presence of diethyl ether. The product is isolated and dried. Thus, 176 mg of the desired product, i.e. the title compound of Example 16, was obtained, which had an Rf value of 0.34 (hexane / ethyl acetate 1:1). HU 222 787 B1 Ή-NMR spectrum (300 MHz, DMSO-d6, δ ppm): 1.08 (s, 3H), 1.30 (s, 3H), 2.22 (s, 3H), 2.25 (s, 3H), 3.47 (s, 3H), 3.65 (d, 1H, J=10.0 Hz), 3.90 (s, 3H), 4.16 (m, 1H), 5.48 (dd, 1H, J=3.0 and 10.0 Hz), 5.61 (d, 1H, J=2.0 Hz), 5.70 (d, 1H, J=5.0 Hz), 5.93 (m, 1H), 6.78 (m, 1H), 7.16 (d, 1H, J=9.0 Hz), 7.78 (d, 1H, J=9.0 Hz), 8.35 (s, 1H), 11.66 (broad s). Example 17 Preparation of 3-Acetyl-7-[(6-deoxy-5-C-methyl-4-O-methyl-aL-lyxo-hexopyranosyl)-oxy]-4-hydroxy-8-methyl-2H-l-benzopyran-2-one-3'-cyclopropylcarbamic acid ester Step A: 7-[(6-Deoxy-5-C-methyl-4-O-methyl-aL-lyxo-hexopyranosyl)oxy]-8-methyl-4-(2-propenyloxy)-2H-1-benzopyran-2-one 8.50 g product prepared in Preparation Example 2, 8.44 g To a mixture of 6-deoxy-5-C-methyl-4-O-methyl-L-lyxohexopyranose, 11.52 g triphenylphosphine, 100 ml DCM and 20 ml THF, 8.10 ml diethyl azodicarboxylate was added dropwise, the reaction mixture was stirred for 2 hours at ambient temperature, and 5.70 g triphenylphosphine and 4.05 ml diethyl azodicarboxylate were added. The product obtained was then chromatographed on silica gel, eluting with a 90:10 mixture of DCM and acetone. After evaporation and drying, the desired product was obtained in a yield of 8.304 g. Step B): 7-[(2,3-O-Carbonyl-6-deoxy-5-C-methyl-4-O-methyl-aL-lyxohexopyranosyl)oxy]-8-methyl-4-(2-propenyloxy)-2H1-benzopyran-2-one g of the product prepared in step A) and 1.995 g of carbonyldiimidazole are refluxed for 30 minutes, then the reaction mixture is cooled and diluted with 100 ml of a 1:1 mixture of THF and ethyl acetate. The mixture is washed with water, dried and evaporated after filtration. The residue is dissolved in DCM and chromatographed on silica gel. Elution is carried out with a 9:1 mixture of DCM and acetone. After evaporation of the solvents, 1.32 g of the desired product are obtained, with an Rp value of 0.69 (DKM / acetone 90:10). Step C: 7-[(2,3-O-Carbonyl-6-deoxy-5-C-methyl-4-O-methyl-a.-L-lyxohexopyranosyl)oxy]-4-hydroxy-8-methyl-2H-1-benzopyran-2-one g To a mixture of the product obtained in the previous step and 10 ml of THF, 267 mg of palladium tetrakis(triphenylphosphine) are added, and the reaction mixture is stirred for 30 minutes at 0 °C, then 10 ml of diethyl ether are added and then filtered. The product thus obtained is separated, rinsed with a 1:1 mixture of diethyl ether and THF and dried. Thus, 880 mg of product is obtained, which is poured into 75 ml of a 2:2:1 mixture of THF / ethyl acetate / hexane. The aqueous phase is extracted with the same solvent mixture. The combined organic phase was dried, filtered and evaporated to give 726 mg of the desired product of step C). Step D: 3-Acetyl-7-[(2,3-O-carbonyl-6-deoxy-5C-methyl-4-O-methyl-a.-L-lyxo-hexopyranosyl)-oxy]-4-hydroxy-8-methyl-2H-1-benzopyran-2-one To a solution of 1.29 g of the product obtained in step C), 1.344 g of 4-(dimethylamino)pyridine, 719 mg of N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride and 15 ml of DCM, 225 µl of acetic acid were added. The mixture was stirred for 6 hours at ambient temperature, then diluted with 50 ml of DCM, washed with 10% aqueous sodium hydrogen sulfate solution and the organic solution was dried. After evaporation of the solvents, the product obtained was chromatographed on silica gel, elution being carried out with a mixture of DCM and methanol in a ratio of 98:2. The product obtained after evaporation of the solvents was dried to give 1.18 g of the desired compound, whose Rf value was 0.73 (DCM / methanol 94:6). Step E: 3-Acetyl-7-[(6-deoxy-5-C-methyl-4-O-methyl-αL-lyxohexopyranosyl)oxy]-4-hydroxy-8-methyl-2H-1-benzopyran-2-one To a solution of 1.137 g of the product obtained in the previous step and 5 ml of DMF, 783 µl of di(tert-butyl) ether and 362 µl of cyclopropylamine were added, and the reaction mixture was stirred for 3 hours, after which 181 µl of cyclopropylamine was added. Stirring was continued for another 3 hours, and the reaction mixture was poured into a mixture of 80 ml of a 1:2 mixture of hexane-ethyl acetate and an aqueous solution of sodium hydrogen sulfate. Extraction was carried out with a 1:2 mixture of hexane and ethyl acetate. The combined organic phase was washed, dried, filtered and evaporated. The evaporation residue was dried to give 1.040 g of the desired product, i.e. the title compound of Example 17, with an Rf value of 0.58 (DKM / methanol 90:10). H-NMR spectrum (300 MHz, DMSO-d6, δ ppm): «0.43 (m, 2H), 0.60 (m, 2H), 1.04 (s, 3H), 1.18 (s, 3H), 2.19 (s, 3H), 2.65 (s, 3H), 3.12 (m, 1H), 3.45 (s, 3H), -3.49 (m, 1H), -4.02 (broad s, 1H), 5.18 (dd, 1H, J=3.0 and 10.0 Hz), 5.60 (broad s, 1H), 7.21 (d, 1H, J=9.0 Hz), 7.50 (broad s, 1H), 7.90 (d, 1H, J=9.0 Hz), 13.75 (broad s, 1H). Example 18 (E) Preparation of 7-[(6-Deoxy-5-C-methyl-4-O-methyl-dL-lyxohexopyranosyl)oxy]-4-hydroxy-3-[1-(methoxyimino)ethyl]methyl-2H-1-benzopyran-2-one-3'-(cyclopropylcarbamic acid) ester A mixture of 100 mg of the compound prepared in the previous example, 34 mg of methoxyamine hydrochloride, 50 mg of potassium acetate and 2 ml of ethanol is heated under reflux for 1 hour, after which the ethanol is completely evaporated and the residue is taken up in 40 ml of DCM. The solution is washed with 1 molar aqueous sodium dihydrogen phosphate solution, then dried over anhydrous magnesium sulfate, and after evaporation of the solvent, preparative layer chromatography is carried out. After extraction, the solvents are evaporated, the resulting residue is dissolved in diethyl ether and n-pentane is added. The product thus separated is separated and dried, thus obtaining 56 mg of the desired product, whose Rf value is 0.41 (DCM / methanol 94:6). Ή-NMR spectrum (300 MHz, DMSO-d6, δ ppm): 0.44 (m, 2H), 0.60 (m, 2H), 1.04 (s, 3H), 1.26 (s, 3H), 2.20, (s, 3H), 2.27 (s, 3H), 3.45 (m, 1H), 3.45 (s, 3H), 3.95 (s, 3H), 4.09 (m, 1H), 5.19 (dd, 1H, J=3.0 and 10.0 Hz), 5.55 (broad s, 1H), 5.64 (d, 1H, HU 222 787 Bl J=5.0 Hz), 7.16 (d, 1H, J=9.0 Hz), 7.51 (m, 1H), 7.79 (d, 1H, J=9.0 Hz), 13.67 (ml, 1H). Example 19 (E) Preparation of 7-[(6-Deoxy-5-C-methyl-4O-methyl-α-L-lyxohexopyranosyl)oxy]-3-(1-dimethylhydrazono)ethyl-4-hydroxy8-methyl-2H-1-benzopyran-2-one-3'-(cyclopropylcarbamic acid) ester The procedure described in the previous example is followed, but N,N-dimethylhydrazine is used instead of methoxyamine hydrochloride, and thus the desired product is obtained. Ή-NMR spectrum (300 MHz, DMSO-d6, δ ppm): 0.43 (m, 2H), 0.60 (m, 2H), 1.04 (s, 3H), 1.25 (s, 3H), 2.16 (s, 3H), 2.68 (s, 6H), 2.76 (s, 3H), 3.44 (s, 3H), 3.48 (d, 1H, J=10.0 Hz), 4.07 (broad s, 1H), 5.18 (dd, 1H, J=3.0 and 10.0 Hz), 5.51 (broad s, 1H), 5.61 (d, 1H, J=5.0 Hz), 7.05 (d, 1H, J=9.0 Hz), 7.50 (br s, 1H), 7.78 (d, 1H, J=9.0 Hz), 14.50 (br s, 1H). Example 20 Preparation of 7-[(6-Deoxy-5-C-methyl-4-O-methyl-3-O-(((5-methyl-3-isoxazolyl)-amino)-carbonyl)-a.-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-2-oxo-2H1 -benzopyran-3-carboxylic acid ethyl ester Step A: 7-[(2,3-O-Carbonyl-6-deoxy-5-C-methyl-4-O-methyl-a.-L-lyxohexopyranosyl)oxy]-8-methyl-2-oxo-4-(benzyloxy)-2H1-benzopyran-3-carboxylic acid ethyl ester To a solution of 8.00 g of the product obtained in Preparation Example 3, 5.207 g of 6-deoxy-5-C-methyl-4-O-methyl-L-lyxohexopyranose and 50 ml of DKM, 5.33 ml of diisopropyl azodicarboxylate were added at 0 °C, and the mixture was stirred for 2 hours at ambient temperature. At this time, 3.6 g of triphenylphosphine and 2.7 ml of diisopropyl azodicarboxylate were added, and stirring was continued for another 2 hours. The reaction mixture was evaporated and the residue was chromatographed on silica gel. Elution was carried out with a 2:3 mixture of hexane and ethyl acetate, thus obtaining 8.43 g of product, which was poured into 70 ml of THF. To this mixture was added 5.17 g of carbonyldiimidazole and the reaction mixture was refluxed for 30 minutes, then the solution was cooled and diluted with 100 ml of a 1:2 mixture of hexane and ethyl acetate. The organic solution was washed with aqueous sodium dihydrogen phosphate, dried, and after filtration the solvents were evaporated. The product thus obtained was chromatographed on silica gel.Elution was carried out with a 1:1 mixture of hexane and ethyl acetate. After evaporation of the solvents and drying of the product, 6.48 g of the desired material was obtained. Step B: 7-[(2,3-O-Carbonyl-6-deoxy-5-C-methyl-4-O-methyl-αL-lyxohexopyranosyl)oxy]-4-hydroxy-8-methyl-2-oxo-2 H1-benzopyran-3-carboxylic acid ethyl ester To a solution of 6.00 g of the product obtained in step A) above, 30 ml of ethanol and 15 ml of THF, 600 mg of 10% palladium-on-carbon catalyst were added. This mixture was shaken under hydrogen pressure for 6 hours, then filtered and the precipitate was washed with THF. The product obtained after evaporation of the solvent was dried to give 4.572 g of the desired product, whose Rr value was 0.59 (DKM / methanol 91:9). Step C: 7-[(6-Deoxy-5-C-methyl-4-O-methyl-30-(((5-methyl-3-isoxazolyl)amino)carbonyl)-α-L-lyxohexopyranosyl)oxy]-4-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-carboxylic acid ethyl ester A solution of 254 mg of 5-(methylamino)isoxazole in 2 mL of anhydrous THF was cooled to -76 °C and 1.08 mL of a 1.6 M solution of n-butyllithium in hexane was added at -76 °C. The reaction mixture was stirred for 15 min and then a solution of 400 mg of the product prepared in the previous step in 2 mL of THF was added. The reaction mixture was stirred at -76 °C for 2 h and then at -20 °C for 40 min. It was then diluted with 150 mL of 20% hexane in ethyl acetate and washed with 70 mL of 10% aqueous sodium hydrogen sulfate. After that, it is washed with water and finally with brine, the organic phase is dried and, after filtration, evaporated to dryness, thus obtaining 504 mg of product, which is dissolved in a minimum amount of DCM containing 10% methanol. Chromatographic purification is carried out on silica gel, using DCM containing 10% ethanol as eluent. After evaporation of the solvents, 264 mg of product is obtained, which is chromatographed on silica gel.Elution with DCM / methanol 94:6 gave 145 mg of product. This corresponds to the desired product, i.e. the title compound of Example 20, with an Rf value of 0.21 (DCM / methanol 95:5). Ή-NMR spectrum (300 MHz, DMSO-d6, δ ppm):. 1.05 (s, 3H), 1.28 (m, 3H), 1.28 (m, 3H), 2.19 (s, 3H), 2.37 (s, 3H), 3.49 (s, 3H), 3.57 (d, 1H, J=10.0 Hz), 4.19 (broad s, 1H), 4.32 (q, 2H, J=7.0 Hz), 5.25 (dd, 1H, J=3.0 and 10.0 Hz), 5.61 (broad s, 1H), 5.83 (s, 1H), 6.56 (s, 1H), 7.16 (d, 1H, J=9.0 Hz), 7.83 (d, 1H, 9.0 Hz). Proceeding according to the above example, starting from the product prepared in step B) of the previous example, the following compounds were prepared using the appropriate amines: Example 21 7-[(6-Deoxy-5-C-methyl-4-O-methyl-3-O-(((2-thiazolyl)amino)carbonyl)-a.-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-2-oxo-2H-l-benzopyran-3-carboxylic acid ethyl ester Rf=0.27 (DKM / methanol 95:5). Ή-NMR-spektrum (300 MHz, DMSO-d6, δ ppm): 1.07 (s, 3H), 1.25 (t, 3H, J=7.0 Hz), 1.29 (s, 3H), 2.18 (s, 3H), 3.51 (s, 3H), 3.57 (d, 1H, J=10.0 Hz), 4,21 (m, 3H), 5,28 (dd, 1H, J=3,0 és 10,0 Hz), 5,57 (sz, 1H), 5,80 (d, 1H, J=5,0 Hz), 7,05 (dl, 1H, J=9.0 Hz), 7.77 (d, 1H, J=9.0 Hz), 7.22 (d, 1H, J=3.5 Hz), 7.42 (d, 1H, J=3.5 Hz), 11.95 (széles s, 1H). 22. példa 7- [(6-Dezoxi-5-C-metil-4-O-metil-3-O-(((benzil)-amino)-carbonil)-aL-lixo-hexopiranozil)-oxi]-4-hidroxi8- metil-2-oxo-2Hl-benzopirán-3-karbonsav-etil-észter Rf=0.30 (DKM / metanol 95:5). HU 222 787 Β1 •H-NMR-spektrum (300 MHz, DMSO-d6, δ ppm): 1.02 (s, 3H), 1.27 (s, 3H), 1.32 (t, 3H, J=7.0 Hz), 2.17 (s, 3H), 3.48 (s, 3H), 3.51 (d, 1H, J=10.0 Hz), 4.11 (sz, 1H), 4.21 (m, 2H), 4.37 (q, 2H, J=7.0 Hz), 5.22 (dd, 1H, J=3.0 és 10.0 Hz), 5.59 (d, 1H, J=2.0 Hz), 5.71 (1, 1H), 7.21 (d, 1H, J=9,0 Hz), 7,30 (ml, 5H), 7,85 (d, 1H, J=9,0 Hz), 7,92 (t, 1H, J=6,0 Hz). 23. példa 7-[(3-O-(((Ciklopentil)-amino)-carbonil)-6-dezoxi-5C-metil-4-O-metil-a.-L-lixo-hexopiranozil)-oxi]-4-hidroxi-8-metil-2-oxo-2H-l-benzopirán-3-karbonsavetil-észter Rf=0.32 (DKM / metanol 95:5). •H-NMR-spektrum (300 MHz, DMSO-d6, δ ppm): 1.26 (s, 3H), 1.32 (s, 3H), 1.32 (t, 3H, J=7.0 Hz), 1.40-1.90 (m, 8H), 2.18 (s, 3H), 3.46 (s, 3H), 3.50 (d, 1H, J=10.0 Hz), 3.82 (m, 1H), 4.08 (1, 1H), 4.32 (q, 2H, J=7.0 Hz), 5.19 (dd, 1H, J=3.0 és 10.0 Hz), 5.58 (széles s, 1H), 5.64 (1, 1H), 7.18 (d, 1H, J=9.0 Hz), 7.33 (d, 1H, J=7,0 (Hz), 7.85 (d, 1H, J=9.0 Hz). 24. példa 7-[(3-0-(Amino-carbonil)-6-dezoxi-5-C-metil-4-0-metil-aL-lixo-hexopyranozil)-oxi]-4-hidroxi-8-metil-2oxo-2H-l-benzopirán-3-carbonsav-etil-észter Rf=0.06 (DKM / metanol) 95:5). •H-NMR-spektrum (300 MHz, DMSO-d6, δ ppm): 1.03 (s, 3H), 1.26 (s, 3H), 1.32 (t, 3H, J=7.0 Hz), 5.58 (d, 1H, J=2.5 Hz), 6.55-6.75 (1, 2H), 7.19 (d, 1H, J=9.0 Hz), 7.85 (d, 1H, J=9.0 Hz). 25. példa 7-[(6-Dezoxi-5-C-metil-4-O-metil-3-O-(((2-piridinilmetil)-amino-carbonil)-a.-L-lixo-hexopiranozil)-oxi]4-hidroxi-8-metil-2-oxo-2H-l-benzopirán-3karbonsav-etil-észter Rf=0,l 1 (DKM / metanol 95:5). •H-NMR-spektrum (300 MHz, DMSO-d6, δ ppm): 1.02 (s, 3H), 1.28 (s, 3H), 1.32 (t, 3H, J=7.0 Hz), 2.16 (s, 3H), 3.50 (s, 3H), 3.54 (d, 1H, J=10.0 Hz), 4.11 (sz, 1H), 4.36 (m, 4H), 5.22 (dd, 1H, J=3.0 és 10.0 Hz), 5.60 (d, 1H, J=2.0 Hz), 5.73 (1, 1H), 7.19 (d, 1H, J=9.0 Hz), 7.29 (t, 1H, J=6,0 Hz), 7,36 (d, 1H, J=8,0 Hz), 7,83 (m, 2H), 7,97 (t, 1H, J=6,0 Hz), 8,22 (m, 1H). 26. példa 7-[(3-O-(CUdopropil-amino)-karbonil-6-dezoxi-5-Cmetil-4-O-metil-a.-L-lixo-hexopiranozil)-oxi]-4-hidroxi-8-metil-2-oxo-2Hl-benzopirán-3-karbonsav-etil-észter Rf=0.32 (DKM / metanol 92:8). •H-NMR-spektrum (300 MHz, DMSO-d6, δ ppm): 0.43 (m, 2H), 0.59 (m, 2H), 1.03 (s, 3H), 1.26 (s, 3H), 1.32 (t, 3H, J = 7.0 Hz), 2.19 (s, 3H), 3.45-3.48 (m, 2H), 3.44 (s, 3H), 4.09 (sz, 1H), 4.37 (q, 2H, J = 7.0 Hz), 5.17 (dl, 1H, J=10,0 Hz), 5,58 (szh, 1H), 5,65 (m, 1H), 7,19 (d, 1H, J=9,0 Hz), 7,50 (szh, 1H), 7,85 (d, 1H, J=9,0 Hz). 27. példa 7-[(3-O-(Ciklobutil-amino)-karbonil-6-dezoxi-5-C-metil-4-O-metil-aL-lixo-hexopiranozil)-oxi]-4-hidroxi-8metil-2-oxo-2H-l-benzopirán-3-carbonsav-etil-észter Rf=0.38 (DKM / metanol) 92:8). •H-NMR-spektrum (300 MHz, DMSO-c^, δ ppm): 1.01 (s, 3H), 1.26 (s, 3H), 1.32 (t, 3H, J=7.0 Hz), 1.58 (m, 2H), 1.93 (m, 2H), 2.15 (m, 2H), 2.17 (s, 3H), 3.46 (s, 3H), 3.28 (d, 1H, J=10.0 Hz), 4.00 (m, 1H), 4.07 (sz, 1H), 4.36 (q, 2H, J=7.0 Hz), 5.15 (dd, 1H, J=3.0 és 10.0 Hz), 5.57 (d, 1H, J=2.0 Hz), 5.67 (m, 1H), 7.18 (d, 1H, J=9.0 Hz), 7.63 (d, 1H, J=8.0 Hz), 7,85 (d, 1H, J=9.0 Hz). 28. példa 7-[(6-Dezoxi-5-C-metil-4-O-metil-3-O-(((l-metil-etil)amino)-carbonil)-aL-lixo-hexopiranozil)-oxi]-4-hidroxi-8-metil-2-oxo-2H-l-benzopirán-3-karbonsavetil-észter Rf=0.30 (DKM / metanol 92:8). •H-NMR-spektrum (300 MHz, DMSO-d6, δ ppm): 1.03 (s, 3H), 1.09 (d, 6H, J=6.5 Hz), 1.26 (s, 3H), 1.32 (t, 3H, J=7.00 Hz), 2.18 (s, 3H), 3.46 (s, 3H), 3.50 (d, 1H, J=10.0 Hz), 3.67 (m, 1H), 4.08 (broad s, 1H), 4.37 (q, 2H, J=7.0 Hz), 5.19 (dd, 1H, J=3.0 and 10.0 Hz), 5.58 (d, 1H, J=2.0 Hz), 5.65 (broad s, 1H), 7.18 (d, 1H, J=9.0 Hz), 7.22 (d, 1H, J=7.5 Hz), 7.85 (d, 1H, J=9.0 Hz). Example 29 7-[(6-Deoxy-3-O-(((1,1-dimethylethyl)amino)carbonyl)-5-C-methyl-4-O-methyl-aL-lyxohexopyranosyl)oxy]4-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-carboxylic acid ethyl ester Rf=0.37 (DKM / methanol 92:8). H-NMR spectrum (300 MHz, DMSO-d6, δ ppm): 1.02 (s, 3H), 1.26 (s, 12H), 1.32 (t, 3H, J=7.0 Hz), 2.19 (s, 3H), 3.46 (s, 3H), 4.06 (broad s, 1H), 4.37 (q, 2H, J=7.0 Hz), 5.17 (dd, 1H, J=3.0 and 10.0 Hz), 5.58 (d, 1H, J=2.5 Hz), 5.62 (broad s, 1H), 7.03 (broad s, 1H), 7.19 (d, 1H, J=9.0 Hz), 7.85 (d, 1H, J=9.0 Hz). Example 30 7-[(3-O-((Cyclohexylamino)carbonyl)-6-deoxy-5-Cmethyl-4-O-methyl-(iL-lyxohexopyranosyl)oxy]-4-hydroxy-8-methyl-2-oxo-2H1-benzopyran-3-carboxylic acid ethyl ester Rf = 0.33 (DKM / methanol 92:8). H-NMR spectrum (300 MHz, DMSO-d6, δ ppm): 1.00-1.80 (m, 10H), 1.03 (s, 3H), 1.26 (s, 3H), 1.32 (t, 3H, J=7.0 Hz), 2.18 (s, 3H), 3.46 (s, 3H), 3.63 (d, 1H, J=10.0 Hz), 4.08 (broad s, 1H), 4.37 (q, 2H, HU 222 787 Bl J=7.0 Hz), 5.20 (dd, 1H, J=3.0 and 10.0 Hz), 5.61 (d, 1H, J=2.0 Hz), 5.65 (broad s, 1H), 7.19 (d, 1H, J=9.0 Hz), 7.25 (d, 1H, J=8.0 Hz), 7.86 (dd, 1H, J=9.0 Hz). Example 31 7-[(6-Deoxy-5-C-methyl-4-O-methyl-3-O-((4-methyl-l-piperazinyl)-carbonyl)-a.-L-lyxo-hexopyranosyl)-oxy]-4-hydroxy-8-methyl-2-oxo-2Hl-benzopyran-3-carboxylic acid ethyl ester Rf=0.22 (DKM / methanol 85:15). • H-NMR spectrum (300 MHz, DMSO-d6, δ ppm): 1.02 (s, 3H), 1.20 (t, 3H, J=7.0 Hz), 1.30 (s, 3H), 2.12 (s, 3H), 2.60 (broad s, 3H), 3.04 (1, 8H), 3.44 (s, 3H), 3.54 (d, 1H, J=10 Hz), 4.05 (m, 3H), 5.4 (dd, 1H, J=3 and 10 Hz), 5.50 (d, 1H, J=2.0 Hz), 5.62 (d, 1H, J=4.5 Hz), 6.93 (d, 1H, J=9.0 Hz), 7.65 (d, 1H, J=9.0Hz). Example 32 (Z) Preparation of 7-[(6-Deoxy-5-C-methyl-4-O-methyl-2,3-O-(1-methylethylidene)-αL-lyxohexopyranosyl)oxy]-4-hydroxy-3[1-hydroxy-2-(2-pyridinyl)ethenyl]-8-methyl-2H-1-benzopyran-2-one To a solution of 1.452 g (Z) 7-[(6-deoxy-5-C-methyl-4-O-methyl-2,3O-(1-methylethylidene)-aL-lyxohexopyranosyl)oxy]-4-hydroxy-8-methyl-2H-1-benzopyran-2-one and 15 ml anhydrous DCM, 611 mg 2-pyridinylacetic acid hydrochloride and 1.29 mg 4-(dimethylamino)pyridine were added, followed by 606 μΐ diisopropylcarbodiimide, and the reaction mixture was stirred for 20 hours. Then 305.5 mg of 2-pyridinylacetic acid hydrochloride and 0.645 mg of 4-(dimethylamino)pyridine are added and stirring is continued for 12 hours, then the mixture is diluted with 250 ml of DCM, washed with 70 ml of 1 N aqueous sodium dihydrogen phosphate solution, then with water, finally with brine, dried, filtered and evaporated to dryness. The 4.06 g of product thus obtained is taken up in diethyl ether at 0 °C; after separation, 1.594 g of product is obtained, which is chromatographed on silica gel. Using a 96.5:3.5 mixture of DCM and methanol as eluent, 1.54 g of product is obtained, which is thoroughly triturated with absolute ethanol and cooled to -10 °C.After separation and drying, the mother liquors were evaporated to dryness to give 0.317 g of product, which was triturated thoroughly with 5 ml of ethanol containing 4 ml of ether. After isolation and drying, 287 mg of the desired product were obtained, with an Rf value of 0.40 (DKM / methanol 95:5). Example 33 (Z) Preparation of 7-[(6-Deoxy-5-C-methyl-4-O-methyl-α-L-lyxohexopyranosyl)oxy]-4-hydroxy-3-[1-hydroxy-2-(2-pyridinyl)ethenyl]-8-methyl-2H-1-benzopyran-2-one 1.15 g of the compound prepared in the previous example is added to a 10% aqueous trifluoroacetic acid solution at 0 °C, stirred for 4 minutes at 0 °C, then 80 ml of a buffer solution containing 40 ml of a 2 molar potassium dihydrogen phosphate solution and 40 ml of a 2 molar dipotassium hydrogen phosphate solution are added. The precipitate is separated, dissolved in DKM and It is taken up in THF, washed with 10% sodium bicarbonate solution, then with concentrated sodium chloride solution, and dried. After distilling off the solvents, 1.09 g of the product obtained is dispersed in 4 ml of absolute ethanol. The insoluble part is separated by filtration, washed with ethanol, and dried. Thus, 291 mg of the desired product is obtained. Example 34 (Z) Preparation of 7-[(6-Deoxy-5-C-methyl-4-O-methyl-thiL-lyxo-hexopyranosyl)-oxy]-4-hydroxy-3-[1-hydroxy-2(2-pyridinyl)-ethenyl]-8-methyl-2H-1-benzopyran-2-one 3'-carboxylic acid ester Step A: (Z) 7-[(2,3-O-Carbonyl-6-deoxy-5-Cmethyl-4-O-methyl-a.-L-lyxo-hexopyranosyl)-oxy]-4-hydroxy-3-[l-hydroxy-2-(2-pyridinyl)-ethenyl]-8-methyl-2H-1-benzopyran-2-one To a solution of 210 mg of the product prepared in the previous example and 10 ml of THF, 84 mg of carbonyldiimidazole were added and the reaction mixture was refluxed for 1 hour, then 40 mg of carbonyldiimidazole were added and refluxing was continued for 1 hour. The mixture was diluted with ethyl acetate, washed with 1 molar sodium dihydrogen phosphate solution, then with brine, dried, filtered and evaporated to dryness. The residue thus obtained was dried to give 107 mg of the desired product. Step B: (Z) 7-[(6-Deoxy-5-C-methyl-4-O-methyl-L-lyxo-hexopyranosyl)-oxy]-4-hydroxy-3-[1-hydroxy-2-(2-pyridinyl)-ethenyl]-8-methyl-2H-1-benzopyran-2-one· 3 '-carbamic acid ester Approximately 15 ml of ammonia is liquefied in a flask and 107 mg of the product prepared in step A) is added. The reaction mixture is refluxed at the boiling point of ammonia for 30 minutes with stirring, and the ammonia is then allowed to evaporate. The product thus obtained is poured into 100 ml of THF in the presence of 50 ml of 10% aqueous sodium hydrogen sulfate. The organic solution is washed with concentrated brine, dried, and evaporated to dryness after filtration. The residue is thoroughly sonicated in the presence of diisopropyl ether, and the product is isolated and dried. This gives the desired product, the title compound of Example 34, in a yield of 89 mg, with an Rf value of 0.27 (DKM / methanol 90:10). • H-NMR spectrum (300 MHz, DMSO-d6, δ ppm): 1.05 (s, 3H), 1.26 (s, 3H), 2.19 (s, 3H), 3.47 (s, 3H), 3.50 (1, 1H), 4.07 (broad s, 1H), 5.15 (dd, 1H, J=3.0 and 10.0 Hz), 5.52 (d, 1H, J=2.5 Hz), 5.60 (broad s, 1H), 6.50-6.70 (1.2H), 6.82 (s, 1H), 7.05 (t, 1H, J=8.0 Hz), 7.09 (d, 1H, J=9.0 Hz), 7.63 (m, 1H), 7.79 (d, 1H, J = 9.0 Hz), 7.92 (ti, 1H, J=7.5 Hz), 8.16 (t, 1H, J=6.0 Hz), 13.81 (broad s, 1H), 16.0 (broad s, 1H). Example 35 Preparation of 7-[(6-Deoxy-5-C-methyl-4-O-methyl-aL-lyxo-hexopyranosyl)-oxy]-4-hydroxy-8-methyl-2-oxo-2H1-benzopyran-3-carboxamide-3'-(5-methyl-1H-pyrrole-2carboxylic acid)-ester HU 222 787 Bl Step A: 7-[(6-Deoxy-5-C-methyl-4-O-methyl-20-(tetrahydro-2H-pyran-2-yl)-o.-L-lyxohexopyranosyl)oxy]-8-methyl-2-oxo-4(benzyloxy)-2H-1-benzopyran-3-carboxylic acid ethyl ester-(5-methyl-1H-pyrrole-2-carboxylic acid-3')-ester 1.3 ml of 1,2-dihydropyran, followed by 70 mg of PTSA, were added to a solution of 4.52 g of the product prepared in step A of Example 4. The reaction mixture was stirred at ambient temperature for 90 minutes, then washed with sodium carbonate solution, dried over anhydrous magnesium sulfate, and filtered. Purification was carried out by chromatography on silica gel, eluting with hexane:ethyl acetate (7:3). This gave 1.92 g of the desired product with an Rf of 0.38 (hexane / ethyl acetate 1:1). Step B: 7-[(6-Deoxy-5-C-methyl-4-O-methyl-2O-(tetrahydro-2H-pyran-2-yl)- <x-L-lixohexopiranozil)-oxi]-4-hidroxi-8-metil-2oxo-2H-l-benzopirán-3-karbonsav-etilészter-(5-metil-lH-pirrol-2-karbonsav3)-észter To a solution of 1.92 g of the product obtained in step A) and 25 ml of THF, 200 mg of palladium-on-carbon catalyst were added, and the reaction mixture was stirred at ambient temperature under hydrogen pressure for 1 hour, then filtered to remove the catalyst. The solvent was evaporated to dryness from the filtrate. The residue was dissolved in diethyl ether, precipitated with hexane, the solvent was evaporated to dryness, and the residue was dried in vacuo. Thus, 1.629 g of the desired product was obtained, whose Rf value was 0.30 (hexane / ethyl acetate 1:4). Step C: 7-[(6-Deoxy-5-C-methyl-4-O-methyl-aL-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-carboxamide-3'-(5-methyl-1H-pyrrole-2-carboxylic acid) ester A solution of 350 mg of the product obtained in the previous step and 10 ml of THF was saturated at 0 °C by bubbling ammonia through it, and the reaction mixture was stirred at ambient temperature for 2 days, then diluted with 50 ml of a 1:4 mixture of hexane and ethyl acetate, washed with 50 ml of 10% aqueous sodium hydrogen sulfate solution, dried and evaporated to dryness. The 340 mg of product thus obtained was dissolved in 10 ml of methanol and 10 ml of DCM, 50 mg of PTSA monohydrate was added and stirred at ambient temperature for 3 hours, then diluted with 70 ml of DCM. The organic solution was first washed with saturated aqueous sodium hydrogen carbonate solution, then dried and evaporated to dryness. The residue was thoroughly triturated in the presence of diisopropyl ether, and the insoluble portion was separated, yielding 170 mg of the desired product, i.e. the title compound of Example 35. H-NMR spectrum (300 MHz, DMSO-d6, δ ppm): 1.07 (s, 3H), 1.30 (s, 3H), 2.23 (s, 3H), 2.24 (s, 3H), 3.47 (s, 3H), 3.66 (d, 1H, J=10 Hz), 4.18 (broad s, 1H,), 5.48 (dd, 1H, J=3 and 10 Hz), 5.66 (d, 1H, J=2.5 Hz), 5.74 (broad s, 1H), 5.93 (t, 1H, J = 3 Hz), 6.78 (t, 1H, J = 3 Hz), 7.24 (d, 1H, J=9 Hz), 7.85 (d, 1H, J=9 Hz), 8.73 (broad s, 1H H), 8.98 (br s, 1H), 11.66 (br s, 1H), 13.50 (br s, 1H). Example 36 Preparation of 3-(Cyclopropylcarbonyl)-7-[(6-deoxy-5-C-methyl-4-Omethyl-a.-L-lyxohexopyranosyl)oxy]-4-hydroxy-8-methyl2-oxo-2H-1-benzopyran-2-one-(5-methyl-1H-pyrrole-2-carboxylic acid-3)-ester To a solution of 400 mg of the product prepared in step C of Example 1, 173 mg of N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride and 306 mg of 4-(dimethylamino)pyridine in DCM, 78 μΐ of cyclopropanecarboxylic acid were added and the mixture was stirred for 5 hours at ambient temperature. At this time, 86 mg of N-(3-dimethylaminopropyl)N'-ethylcarbodiimide hydrochloride and 159 mg of 4-(dimethylamino)pyridine were added. Stirring was continued overnight at ambient temperature, then the reaction mixture was diluted with 50 ml of DCM, washed with 50 ml of 10% aqueous sodium hydrogen sulfate solution and dried. The solution was evaporated to dryness to give 408 mg of product (Rr = 0.78, developer: DCM:methanol 94:6). The product was dissolved in 15 mL of methanol and 10 mL of DCM, 60 mg of PTSA was added, and stirring was continued at ambient temperature for 3 h, then the mixture was diluted with DCM, washed with aqueous sodium bicarbonate, dried over anhydrous magnesium sulfate, and evaporated to dryness.The product was purified by chromatography on silica gel, eluting with a mixture of DCM and methanol (94:6). The product obtained was dissolved in 1 ml of diethyl ether and precipitated by adding 5 ml of n-pentane. The product was isolated and dried to give the desired title compound. Yield: 139 mg. 'H-NMR spectrum (300 MHz, DMSO, δ ppm): 1.07 (s, 3H), 1.30 (s, 3H), 1.24 (broad s, 2H), 1.27 (broad s, 2H), 2.24 (s, 3H), 2.25 (broad s, 3H), 3.48 (s, 3H), 3.58 (m, 1H), 3.66 (d, 1H, J=10 Hz), 4.18 (1, 1H), 5.48 (dd, 1H, J=3 and 10 Hz), 5.68 (d, 1H, J=2.5 Hz), 5.75 (d, 1H, J=5 Hz), 5.93 (t, 1H, J=3 Hz), 6.79 (t, 1H, J=3 Hz), 7.24 (d, 1H, J=9 Hz), 7.91 (d, 1H, J=9 Hz), 11.67 (s, 1H), 13.88 (1.1H). Example of medicinal products We produce tablets with the following composition: Compound of Example 4 150 mg Excipients as needed for 1 g Excipients in more detail: starch, talc, magnesium stearate Compound of Example 5 150 mg Excipients as needed for 1 g Excipients in more detail: starch, talc, magnesium stearate Compound of Example 2 150 mg Excipients as needed for 1 g Excipients in more detail: starch, talc, magnesium stearate Injectable solutions are prepared from salts. HU 222 787 Bl Pharmacological testing of the compounds of the invention A) The dilution method in a liquid medium A series of test tubes is prepared and an equal amount of sterile culture medium is added to each tube. Increasing amounts of the compound to be tested are added to each tube, and each tube is then inoculated with a bacterial strain. The test tubes are incubated in a heat chamber at 37 °C for 24 hours, and the inhibition of bacterial growth is then assessed by transillumination, which allows the determination of the minimum inhibitory concentration (MIC value). The latter is expressed in units of pg / cm3. The following strains were tested: S. aureus 011HT3 S. aureus 011UC4 S. aureus 011HT28 S. epidermidis 012G020 S. aureus 011DU5 S. aureus 011CB20 S. aureus 011HT26 S. epidermidis 012GO39 S. epidermidis 012HI1 Staph. coag. negative 012HT5 Staph. coag. negative 014HI1 S. pyogenes 02A1UC1 We obtained the following results: 0.04 <MIC nagyobb 20 B) Inhibition of the enzyme gyrase B The compounds of the invention inhibit the enzyme gyrase B; their dose causing 50% supercoiling of DNA is less than 5 pg / ml.

Claims

PATENT CLAIMS 1. Compounds of general formula (I) and their salts, where in the formula Rj represents a hydrogen atom; a hydroxyl group; an alkyl, alkenyl or alkynyl group optionally interrupted by an oxygen, sulfur or nitrogen atom, having up to 12 carbon atoms, a straight or branched carbon chain or a cyclic group optionally substituted with one or more halogen atoms, one or more hydroxyl groups, C=N, NO2, NRaR{, group, where Ra and Rb are the same or different and represent a hydrogen atom; an alkyl group containing up to 8 carbon atoms; or Ra and Rb together with the nitrogen atom to which they are attached may form a heterocyclic group containing an additional nitrogen, sulfur or oxygen atom; or Rj represents an alkoxy group containing up to 8 carbon atoms, optionally substituted with one or more of the above substituents; or R1 is a group of the general formula NRcRd, in which Rc and Rd are the same or different and represent a hydrogen atom;or optionally interrupted by oxygen, sulfur or nitrogen atoms, an alkyl group of up to 12 carbon atoms, optionally substituted with one or more of the above substituents; or Rc and Rd may also form a heterocyclic group with the nitrogen atom to which they are attached, optionally containing nitrogen, sulfur or oxygen atoms as a further heteroatom; X represents an oxygen atom; or a group of the general formula N-NaUq or NOalk2, where alk! and alk2 are optionally interrupted by oxygen, sulfur or nitrogen atoms, optionally substituted with one or more halogen atoms, one or more groups of the general formula NReRf, in which Re and Rf are the same or different and represent a hydrogen atom; an alkyl group of up to 8 carbon atoms, optionally substituted;or Re and Rf together with the nitrogen atom to which they are attached may also form a heterocyclic group which may contain an oxygen, sulfur or nitrogen atom as a further heteroatom; R2 represents a hydrogen or halogen atom; R3 represents a hydrogen or halogen atom; or an alkyl group containing up to 8 carbon atoms; R4 represents a group of the general formula NRgRh, in which Rg and Rh are the same or different and represent a hydrogen atom; a straight or branched or cyclic aryl or heteroaryl group containing up to 8 carbon atoms, optionally substituted; or Rg and Rf together with the nitrogen atom to which they are attached may also form a heterocyclic group which may contain an additional oxygen, sulfur or nitrogen atom; or R4 is an aryl or heteroaryl group optionally substituted with one or more halogen atoms, one or more hydroxyl groups, one or more alkyl or alkoxy groups having up to 8 carbon atoms; R5 is a hydrogen atom;an O-alkyl group containing up to 4 carbon atoms; R6 is an alkyl or CH2-O-alkyl group in which the alkyl group contains up to 8 carbon atoms; and R7 is a hydrogen atom; or an alkyl group containing up to 8 carbon atoms.; 2. Compounds of general formula (I) according to claim 1, wherein R2 represents a hydrogen atom.

3. Compounds of formula (I) according to claim 1 or 2, wherein R3 is methyl.

4. Compounds of general formula (I) according to any one of claims 1 to 3, wherein R1 is a methyl group.

5. Compounds of general formula (I) according to any one of claims 1-4, wherein R7 represents a hydrogen atom or a methyl group.

6. Compounds of general formula (I) according to any one of claims 1-5, wherein R5 represents an OCH3 group.

7. Compounds of general formula (I) according to any one of claims 1-6, wherein R4 is a group of formula (a). HU 222 787 Bl 8. Compounds of general formula (I) according to any one of claims 1-6, wherein R4 represents an NHcyclopropyl group.

9. Compounds of general formula (I) according to any one of claims 1-8, wherein X represents an oxygen atom.

10. Compounds of formula (I) according to any one of claims 1-8, wherein X is a group of formula NOR, in which R is an alkyl group optionally substituted by one or more halogen atoms and optionally interrupted by oxygen, nitrogen, sulfur atoms and optionally carrying an optionally substituted heterocyclic group.

11. Compounds of general formula (I) according to claim 10, wherein X represents a NOCH3 group.

12. Compounds of general formula (I) according to any one of claims 1-11, wherein Rj represents an alkyl group optionally interrupted by an oxygen or sulfur atom, an O-alkyl group optionally interrupted by an oxygen or sulfur atom or by an NH2 group.

13. Compounds of general formula (I) according to claim 12, wherein R 1 represents CH 3 , -CH 2 -S-CH 3 , -CH 2 O-CH 2 -CH 3 , NH 2 , OC 2 H 5 or -CH 2 -CH(CH 3 ) 2 .

14. Compounds of general formula (I) according to claim 13, wherein Rj represents a methyl or O-ethyl group.

15. The following compounds of general formula (I), by their chemical names: - 3-acetyl-7-[(6-deoxy-5-C-methyl-4-O-methyl-aL-lyxo-hexopyranosyl)-oxy]-4-hydroxy-8-methyl2H-1-benzopyran-2-one-(5-methyl-1H-pyrrole-2-carboxylic acid-3')-ester; - ethyl-7-[(6-deoxy-5-C-methyl-4-O-methyl-aL-lyxo-hexopyranosyl)-oxy]-4-hydroxy-8-methyl-2oxo-2H-1-benzopyran-3-carboxylate-(5-methyl-1H-pyrrole-2-carboxylic acid-3')-ester; - 7-[(6-deoxy-5-C-methyl-4-O-methyl-aL-lyxohexopyranosyl)oxy]-4-hydroxy-3-[1-(methoxyimino)ethyl]-8-methyl-2H-1-benzopyran-2-one-(5methyl-1H-pyrrole-2-carboxylic acid-3')-ester; - 7-[(6-deoxy-5-C-methyl-4-O-methyl-aL-lyxohexopyranosyl)oxy]-3-(ethoxyacetyl)-4-hydroxy-8methyl-2H-1 -benzopyran-2-one-(5-methyl-1H-pyrrole2-carboxylic acid-3')-ester; - 3-(cyclopropylcarbonyl)-7-[(6-deoxy-5-C-methyl4-O-methyl-α-L-lyxohexopyranosyl)oxy]-4-hydroxy-8-methyl-2H-1-benzopyran-2-one-(5-methyl1H-pyrrole-2-carboxylic acid-3')-ester;and - 7-[(6-deoxy-5-C-methyl-4-O-methyl-α-L-lyxohexopyranosyl)oxy]-4-hydroxy-8-methyl-2-oxo2H-1-benzopyran-3-carboxamide-(5-methyl-1H-pyrrole-2-carboxylic acid-3')-ester.; 16. A process for the preparation of compounds of general formula (I) according to any one of claims 1-15 - where the substituents have the meaning as defined in claim 1, characterized in that a compound of general formula (II) - where Rg represents a free or protected hydroxyl group; Z represents a hydrogen atom or a group of general formula C(=X)-Rj; X, Rj, R2 and R3 have the meanings as above; ORg represents a free or protected hydroxyl group - is reacted with a compound of general formula (III) where R5, Re and R7 have the meanings as above; OR'4 represents a protected hydroxyl group; R"4 represents a hydrogen atom; or R'4 and R"4 taken together with the carbon atom to which they are attached may also form a group of formula (b), and thus a compound of general formula (IV) is obtained, where the substituents have the meanings as above; - then the compound of general formula (IV) thus obtained is taken to the following steps (or to one or more of these steps);- the hydroxyl group attached in the 4-position is released, optionally after protection of the hydroxyl group of the sugar in the α-position of the OR'4 group; - if Z is a hydrogen atom, then - optionally after protection of the reactive hydroxyl groups, a group of the general formula -C(=X)-Rj is introduced; - the group of the general formula R'4 is replaced by the group of the formula C(=O)-R4; - the X group is modified.; 17. Compounds of general formulae (II), (III) and (IV) as new chemical products.

18. A pharmaceutical composition comprising as active ingredient at least one compound of general formula (I) according to any one of claims 1-15.