Title of Invention

"NEW AROMATIC AMIDES, THEIR PREPARATION PROCESS AND THEIR USE AS MEDICAMENTS"

Abstract

The compounds of formula (I) in which: - Y represents an oxygen atom, or an N-Nalk1 or NOalk2 radical in which alk1 and alk2 represent an alkyl radical optionally interrupted by an oxygen, sulphur or nitrogen atom, containing up to 12 carbon atoms optionally substituted by one or more halogen atoms, by an aryl radical optionally substituted by one or more halogen atoms, by one or more radicals ,in which Ra and Rb , identical to or different from each other represent a hydrogen atom, an alkyl radical containing up to 8 carbon atoms.

Full Text

The present invention relates to new aromatic amides, their preparation process and their use as medicaments. A subject of the invention is the compounds of general formula (I): (Formula Removed) in which: - Y represents an oxygen atom, or an N-Nalk1 or NOalk2 radical in which alk1 and alk2 represent an alkyl radical optionally interrupted by one or more oxygen, sulphur or nitrogen atoms, containing up to 12 carbon atoms optionally substituted by one or more halogen atoms, by an aryl radical optionally substituted by one or more halogen atoms, by a heterocyclic radical, by one or more (Formula Removed) radicals, in which Ra and Rb identical to or different from each other represent a hydrogen atom, an alkyl radical containing up to 8 carbon atoms, optionally substituted, or Ra and Rb being able to form together with the nitrogen atom to which they are joined a heterocycle which can further contain an oxygen atom, a sulphur atom and another nitrogen atom, X represents a hydrogen atom, a hydroxyl radical, an alkyl, alkenyl or alkynyl radical optionally interrupted by one or more oxygen, sulphur and or nitrogen atoms, containing up to 12 carbon atoms, linear, branched or cyclic, optionally substituted by one or more halogen atoms, by a heterocyclic radical, one or more OH radicals, free or esterified, C=N, (Formula Removed) ,in which Ra and Rb, identical or different, represent a hydrogen atom, an alkyl radical containing up to 8 carbon atoms, or Ra and Rb form together with the nitrogen atom to which they are linked a heterocycle optionally containing another heteroatom chosen from nitrogen, sulphur or oxygen, or X represents an alkoxy radical or a 0 II -C-NORe radical wherein Re is an alkyl radical containing up to 8 carbon atoms, optionally substituted by one or more of the substituents indicated above, or X represents an NRcRd radical in which Rc and Rd, identical or different, represent a hydrogen atom or an alkyl radical containing up to 12 carbon atoms, optionally substituted by one or more of the substituents indicated above, or Rc and Rd form together with the nitrogen atom to which they are linked a heterocycle optionally containing another heteroatom chosen from nitrogen, sulphur or oxygen, - Z represents a hydrogen or halogen atom or an OH radical, free, etherified or esterified, - R2 represents a hydrogen or halogen atom, - R3 represents a hydrogen atom, an alkyl radical containing up to 8 carbon atoms, or a halogen atom - R represents a hydrogen atom or an alkyl radical containing up to 4 carbon atoms, - Rx represents a hydrogen atom, an alkyl, alkenyl or alkynyl radical containing up to 8 carbon atoms, linear, branched or cyclic, optionally substituted by one or more halogen atoms, a C N radical, an aryl radical containing up to 14 carbon atoms, R5 represents a hydrogen atom, an O-alkyl radical containing up to 4 carbon atoms, either R6 represents an alkyl, CH2-0-alkyl radical, in which alkyl represents an alkyl radical containing up to 8 carbon atoms, 2-propenyl or ethenyl and R7 represents a hydrogen atom or an alkyl radical containing up to 8 carbon atoms, or R6 and R7 form together with the carbon atom which carries them, a cycle containing up to 8 carbon atoms, as well as the salts of the compound of formula (I), when the compounds have an basic function. As an example of the addition salts of the present derivatives of formula (I) with acids, there can be mentioned the salts formed with the following acids: acetic, propionic, trifluoroacetic, maleic, tartric, methanesulphonic, benzenesulphonic, p-toluenesulphonic, hydrochloric, hydrobromic, hydroiodic, sulphuric, phosphoric and especially stearic, ethylsuccinic or laurylsulphuric. In the definition of the substituents: - the alkyl, alkenyl or alkynyl radical is preferably a methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, terbutyl, decyl or dodecyl, vinyl, allyl, ethynyl, propynyl, cyclobutyl, cyclopentyl or cyclohexyl radical, - the halogen is preferably fluorine or chlorine, or bromine, - the aryl radical is preferably the phenyl radical, - the heterocyclic radical is preferably the pyrrolyl, pyrrolidinyl, pyridyl, pyrazinyl, pyrimidyl, piperidinyl, piperazinyl, or quinuclidinyl radical, - oxazolyl, - isoxazolyl, morpholinyl, indolyl, imidazolyl, benzimidazolyl, triazolyl, thiazolyl, azetidinyl, aziridinyl. A more particular subject of the invention is the compounds of formula (I) in which Y represents an oxygen atom, those in which Y represents an NO-alkyl radical in which the alkyl radical contains up to 4 carbon atoms, for example those in which Y represents the NOC2H5 radical. Among the preferred compounds of the invention there can be mentioned the compounds of formula (I) in which X represents an alkyl radical containing up to 4 carbon atoms and in particular the CH3 radical, or also those in which X represents an NH2 radical, or also those in which X represents the radical: (Formula Removed) Among the preferred compounds of the invention, there can be mentioned the compounds of formula (I) in which R1 represents a radical: (Formula Removed) those in which R represents a hydrogen atom, or also those in which R3 represents a methyl radical, or also those in which Z represents a hydrogen atom, or also those in which R2 represents a hydrogen atom, or also those in which R5 represents an OCH3 radical, or also those in which R6 represents a methyl radical, or also those in which R7 represents a methyl radical, those in which R7 represents an ethyl radical, those in which R6 and R7 together with the carbon which carries them form a cyclopentyl radical. Among the preferred compounds of the invention, there can be mentioned the compounds the preparation of which is set out below in the experimental part and most particularly the compounds of 1, 2, 3, 4, 5 and 9. The products of general formula (I) have a very good antibiotic activity on gram bacteria such as staphylococci, streptococci, pneumococci, enterococci, listeria, anaerobia. The compounds of the invention can therefore be used as medicaments in the treatment of infections caused by susceptible germs and in particular, in that of staphylococcia, such as staphylococcal septicemias, malignant staphylococcia of the face or skin, pyodermatitis, septic or suppurating wounds, boils, anthrax, phlegmons, erysipelas and acne, staphylococcia such as acute primary or post-influenzal angina, bronchopneumonia, pulmonary suppuration, streptococcia such as acute angina, otitis, sinusitis, scarlet fever, pneumococcia such as pneumonia, bronchitis; brucellosis, diphtheria. The products of the present invention are also active against infections caused by germs such as Haemophilus influenzae. Therefore, a subject of the invention is the compounds of formula (I) as medicaments. A more particular subject of the invention is as medicaments the compounds indicated above as preferred compounds. The invention extends to the pharmaceutical compositions containing at least one of the medicaments as defined above as active ingredient. These compositions can be administered by buccal, rectal, parenteral route or by local route as a topical application on the skin and mucous membranes, but the preferred administration route is the buccal or injectable route. They can be solid or liquid and be presented in the pharmaceutical forms commonly used in human medicine, such as for example, plain or sugar-coated tablets, capsules, granules, suppositories, injectable preparations, ointments, creams, gels; they are prepared according to the usual methods. The active ingredient or ingredients can be incorporated with excipients usually employed in these pharmaceutical compositions, such as talc, gum arabic, lactose, starch, magnesium stearate, cocoa butter, aqueous or non-aqueous vehicles, fatty substances of animal or vegetable origin, paraffin derivatives, glycols, various wetting, dispersing or emulsifying agents, preservatives. These compositions can also be presented in the form of a powder intended to be dissolved extemporaneously in an appropriate vehicle, for example apyrogenic sterile water. The dose administered is variable according to the illness treated, the patient in question, the administration route and the product considered. It can be, for example, comprised between 50 mg and 3 00 0 mg per day by oral or injectable route, in an adult for the preferred products. A subject of the invention is also a preparation process for compounds of formula (I) characterized in that a compound of formula (II): (Formula Removed) in which the R2, R3, Z, R5, R6 and R7 radicals retain their previous meaning, OW represents a blocked hydroxyl group and W represents an alkyl or Oalkyl radical containing up to 4 carbon atoms is subjected - to the action of an agent capable of introducing the radical (Formula Removed) or of a series of operations capable of introducing the radical (Formula Removed) R and R1 retaining their previous meaning, - to the action of an agent capable of releasing the hydroxyl radical from the OW radical, - to the optional action of an agent capable of replacing W with radical X which is different from alkyl or Oalkyl, - to the optional action of an agent capable of introducing radical Y which is different from oxygen, - to the optional of a salification agent. The products of formula (II) used at the start of the process of the invention are new products, the preparation of certain products of formula (II) is given below in the experimental part. The other products of formula (II) can be synthesized by analogy with the processes described in the experimental part. A more particular subject of the invention is the compounds of formula (II) the preparation of which is given in the experimental part. In a preferred implementation: The introduction of the radical (Formula Removed) is carried out in several stages, first by the action of a phenylchloroformate substituted or not, then the action of a compound of formula (Formula Removed) in which Rl and R retain their previous meaning, The OH group is blocked in the form of a tetrahydropyran, The hydrolysis release is carried out by acid hydrolysis, for example by the action of paratoluene sulphonic acid. The optional conversion of the W radical into the X radical and the conversion of the Y radical is carried out according to standard process by the action of an amine. A subject of the invention is also a process characterized in that the product of formula (II) is prepared by the action of a compound of formula (III) (Formula Removed) in which R5, R6 and R7 retain their previous meaning on a compound of formula (IV) (Formula Removed) in which R2, R3 and Z retain their previous meaning, then to the action of a blocking agent of the hydroxyl. The following compounds of formula (III) are new and are themselves a subject of the invention formula, namely: (Formula Removed) The present invention relates to the compounds of formula (I) (Formula Removed) in which: - Y represents an oxygen atom, or an N-Nalk1 or NOalk2 radical in which alk1 and alk2 represent an alkyl radical optionally interrupted by an oxygen, sulphur or nitrogen atom, containing up to 12 carbon atoms optionally substituted by one or more halogen atoms, by an aryl radical optionally substituted by one or more halogen atoms, by one or more radicals (Formula Removed) ,in which Ra and Rb , identical to or different from each other represent a hydrogen atom, an alkyl radical containing up to 8 carbon atoms, optionally substituted, or Ra and Rb being able to form together with the nitrogen atom to which they are joined a heterocycle which can further contain an oxygen or sulphur atom and another nitrogen atom, X represents a hydrogen atom, a hydroxy1 radical, an alkyl, alkenyl or alkynyl radical optionally interrupted by an oxygen, sulphur or nitrogen atom, containing up to 12 linear, branched or cyclic carbon atoms, optionally substituted by one or more halogen atoms, one or more free or esterified OH radicals, C N, (Formula Removed) in which Ra and Rb, identical or different, represent a hydrogen atom, an alkyl radical containing up to 8 carbon atoms, or Ra and Rb form together with the nitrogen atom to which they are linked a heterocycle optionally containing another heteroacom chosen from nitrogen, sulphur or oxygen, or X represents an alkoxy radical or an (Formula Removed) radical wherein Re is an alkyl radical containing' up to 8 carbon atoms, optionally substituted by one or more of the substituents indicated above, or X represents an NKcRd radical in which Re and Rd, identical or different, represent a hydrogen atom or an alkyl radical containing up to 12 carbon atoms, optionally substituted by one or more of the sufostituen-s indicated above, or Rc and Rd form together with the nitrogen atom to which they are linked a heterocycle optionally containing another heteroatotn chosen from nitrogen, sulphur or oxygen,. - Z represents a hydragen or halogen atcm or a f ee, etherified or esterified CH radical, - R2 represents a hydrogen or halogen atom, - R3 represents a hydrogen atom, an alkyl radical containing up to 8 carbon atoms, or a halogen atom, - R represents a hydrogen atOHi or an alkyl radical containing up to 4 carbon atoms, - R1 represents a hydrogen atom, an alkyl, alkenyl or alkynyl radical containing up to 8 carbon atoms, linear, branched or cyclic, optionally substituted by one or more halogen atoms, a C N radical, an aryl radical containing up to 14 carbon atoms, R5 represents a hydrogen atom, an O-alkyl radical containing up to 4 carbon atoms, either R6 represents an alkyl or CH2-O-alkyl radical, in which alkyl represents an alkyl radical containing up to 8 carbon atoms, and / R7 represents a hydrogen atom or an alkyl radical containing up to 8 carbon atoms, or R6 and R7 form together with the carbon atom which carries them a ring containing up to 8 carbon atoms as well as the salts of the compound of formula (I), when the compounds of formula (I) have a basic function. The following examples illustrate the invention without however limiting it. Preparation 1: ethyl 7- [ [6-deoxy-5-C-methyl-4-0-methyl-2-0-(tetrahydro-2H-pyran-2-yl)-alpha-L-lyxo-hexopyranosyl] oxy] -4-hydroxy-8-methyl-2 -oxo-2H-1-benzopyran-3 -carboxylate STAGE A: ethyl 7-[(6-deoxy-5-C-methyl-4-0-methyl-alpha-L-lyxo-hexopyranosyl) oxy] -8-methyl-2-oxo-4- (phenylmethoxy) -2H-1-benzopyran-3-carboxylate A solution containing 80 g of ethyl 7-hydroxy-8-methyl-2-OXO-4-(phenylmethoxy)-2H-l-benzopyran-3-carboxylate in 12 0 0 ml of methylene chloride is agitated under an argon atmosphere. 52.07 g of 6-deoxy-5-C-methyl-4-0-methyl-L-lyxo-hexopyranose and 71.22 g of triphenyl-phosphine are added at 0°C. 54.78 ml of diisopropyl azocarboxylate is introduced at 0°C. After reaction at ambient temperature for one hour, a further 34 g of triphenylphosphine and 25.6 ml of diisopropyl azocarboxylate are added. Agitation is carried out overnight at ambient temperature. Evaporation to one half is carried out, then the suspension is filtered, eluting with a toluene/isopropyl alcohol mixture (95-5). When the product starts to pass through, the operation is continued with a 6% isopropyl alcohol mixture. After impasting in 700 ml of a hexane/ethyl acetate mixture (4-1), 64.4 g of sought product is obtained which is used as it is in the following stage. STAGE B: ethyl 7-[ (6-deoxy-5-C-methyl-4-0-methyl-3-0- (triethylsilyl)-alpha-L-lyxo-hexopyranosyl)oxy]-8-methyl-2- oxo-4-(phenylmethoxy)-2H-l-benzopyran-3-carboxylate 50 g of the solution of Stage A in 500 ml of methylene chloride is agitated under argon at ambient temperature. 42 ml of diisopropylethylamine and 9.66 g of imidazole are added. The solution is agitated for 15 minutes. 20.64 ml of triethylchlorosilane is added dropwise at 0°C over 30 minutes. Agitation is carried out for 2 hours at 0°C. The reaction medium is poured into a molar solution of sodium dihydrogen phosphate. Extraction is carried out using methylene chloride. The extracts are dried and evaporated to dryness. 66.27 g of product is collected which is purified on silica eluting with a mixture of methylene chloride with 0.75% acetone. When the product is practically isolated, elution is carried out with a solution of methylene chloride with 1 % acetone. After impasting in a hexane/ethyl acetate mixture (9-1) 41.04 g of sought product is obtained. NMR 1H (300 MHz, CDC13, ppm) 0.73 (q, 6H), 1.04 (t, 9H), 1.04 (s, 3H), 1.30 (s, 3H), 1.40 (t, 3H), 2.24 (s, 3H), 2.74 (d, J=l Hz, mobile 1H), 3.28 (d, 1H, J=9), 3.53 (s, 3H), 4.05 (m, 1H), 4.27 (dd, 1H, J=3.5 and 9 Hz), 4.43 (q, 2H), 5.31 (s, 2H), 5.62 (d, 1H, J=2 Hz), 7.12 (d, 1H, J=9 Hz), 7.43 (m, 5H), 7.63 (d, 1H, J=9 Hz). STAGE C: ethyl 7-[ [6-deoxy-5-C-methyl-4-0-methyl-2-0-(tetrahydro-2H-pyran-2-yl)-3-0-(triethylsilyl)-alpha-L-lyxo-hexopyranosyl] oxy]-8-methyl-2-oxo-4-(phenylmethoxy)-2H-1-benzopyran-3-carboxylate A solution containing 40.9 g of the product of the previous stage in 400 ml of methylene chloride is agitated under argon at ambient temperature. A few drops of APTS are added, then 11.54 ml of dihydropyrane. Agitation is carried out for 2 hours at ambient temperature. 6 g of sodium bicarbonate is added. The suspension is agitated for 15 minutes then diluted with 1000 ml of a hexane/ethyl acetate mixture (2-1) and poured into water. The reaction medium is decanted, the organic phase is dried over sodium sulphate and evaporated to dryness. 54.67 g of product is obtained which is purified by eluting with a hexane/ethyl acetate mixture (4-1). In this way 36.83 g of sought product is obtained. STAGE D: ethyl 7-[[6-deoxy-5-C-methyl-4-0-methyl-2-0- (tetrahydro-2H-pyran-2-yl)-3-0-(triethylsilyl)-alpha-L-lyxo-hexopyranosyl]oxy]-4-hydroxy-8-methyl-2-oxo-2H-l-benzopyran-3-carboxylate 18 g of the product prepared in the previous stage in solution in 360 ml of tetrahydrofuran is hydrogenated. 0.240 g of palladium on carbon is added and the flask is placed under a hydrogen atmosphere. The reaction medium is filtered. The catalyst is washed with a little tetrahydrofuran. 100 ml of solvent is evaporated off and a solution is obtained which is used as it is in the following stage. STAGE E: ethyl 7-[[6-deoxy-5-C-methyl-4-0-methyl-2-0- (tetrahydro-2H-pyran-2-yl)-alpha-L-lyxo-hexopyranosyl]oxy]-4-hydroxy-8-methyl-2 -oxo-2H-1-benzopyran-3 -carboxylate A solution containing 15.31 g of the product of the previous stage in 250 ml of THF is cooled down under argon to 0°C. 31 ml of tetrabutylammonium fluoride (1M in THF) is added dropwise. The reaction medium is diluted with 400 ml of a hexane/ethyl acetate (1-2) mixture. 300 ml of a 10% solution of sodium hydrogen sulphate is added followed by decanting. The reaction medium is dried and evaporated to dryness. The crude product obtained is solubilized in 20 ml of ethyl ether. The reaction medium is cooled down to -10°C and 8 0 ml of pentane is added under agitation. The suspension obtained is agitated at -20°C, filtered at -16°C. The product obtained is washed with pentane and dried. 9.4 g of sought product is obtained. Preparation 2: 3-acetyl-7-[[6-deoxy-5-C-methyl-4-0-methyl-2-0-(tetrahydro-2H-pyran-2-yl)-alpha-L-lyxo- hexopyranosyl]oxy]-4-hydroxy-8-methyl-2H-l-benzopyran-2-one STAGE A: 4- (diphenylmethoxy) -8-methyl-7- (tetrahydro-2H-pyran-2-yl)-2H-l-benzopyran-2-one 55 g of 4-hydroxy-8-methyl-7-(tetrahydro-2H-pyran-2-yl)-2H-l-benzopyran-2-one is introduced into 250 ml of anhydrous dimethylformamide heated to 40°C, and a solution of 58.3 g of diphenyldiazomethane in 250 ml of DMF is added dropwise. The addition is made over 3 hours while maintaining the temperature at 40°C. Several portions of 3 g of diphenyldiazomethane are again added and agitation is carried out for one hour at 40°C. The reaction medium is poured into 2 1 of sulphuric ether. The organic solution is washed with an aqueous solution of sodium bicarbonate, with a 0.1M soda solution, with water and with salt water. The reaction medium is evaporated to dryness. The residue is agitated in an isopropyl ether-hexane mixture (1-2) then separated. The insoluble part is dried. 20.5 g of sought product is obtained. TLC CH2Cl2-AcOEt (95-5). Rf = 0.44. STAGE B: 4-(diphenylmethoxy)-7-hydroxy-8-methyl-2H-1-benzopyran-2-one 35 ml of a solution of 0.9M hydrochloric acid in methanol is added to a solution containing a mixture of 20 g of the product of Stage A, 100 ml of dichloromethane and 100 ml of methanol. Agitation is carried out for 2 hours at ambient temperature and the solvents are evaporated off. The residue is dispersed in absolute ethanol cooled down to 0°C. The insoluble part is separated off and rinsed with ice-cooled alcohol then with sulphuric ether. The reaction medium is dried and 15.53 g of product is collected which is dispersed in ether, separated and dried. 14.54 g of sought product is obtained. NMR 1H (3 00 MHz, CDC13, ppm) 2.31 (s, 3H), 5.62 (s, 1H), 6.35 (s, 1H), 6.78 (d, 1H, J= _Hz), 7.75 (d, 1H, J= _Hz), 6.99 to 7.10 (m, _H), 7.30 to 7.42 (m, _H) . STAGE, C: 7- [(6-deoxy-5-C-methyl-4-0-methyl-alpha-L-lyxo-hexopyranosyl)oxy]-4-(diphenylmethoxy)-8-methyl-2H-1-benzopyran-2-one A mixture of 91.13 g of the product of Stage B, 58.6 g of 6-deoxy-5-C-methyl-4-0-methyl-L-lyxo-hexopyranose and 80 g of triphenylphosphine in 90 0 ml of dichloromethane are cooled down to 0°C. 60 ml of diisopropylazodicarboxylate is added dropwise. Agitation is carried out for 1 hour at ambient temperature. 34 g of triphenylphosphine and 25 ml of diisopropylazodicarboxylate are added. Agitation is carried out at ambient temperature for 1 hour. 34 g of triphenylphosphine and 25 ml of diisopropylazodicarboxylate are added and agitation is carried out for 12 hours at ambient temperature. The reaction medium is concentrated under vacuum. Chromatography is carried out eluting with a toluene/isopropyl alcohol mixture (95-5). After the fractions are combined and the solvents evaporated off, 86.83 g of sought product is collected after recrystallization from isopropyl ether. NMR 1H (3 00 MHz, CDC13, ppm) 1.13 (s, 3H), 1.37 (s, 3H), 2.24 (s, 3H), 2.69 (s, 1H), 2.79 (s, 1H), 3.38 (d, 1H, J= 10 Hz), 3.60 (s, 3H), 4.24 (m, 1H), 4.28 (m, 1H), 5.56 (s, 1H), 5.64 (d, 1H, J=l.5 Hz), 6.35 (s, 1H), 7.18 (d, 1H), 7.81 (d, 1H), 7.39 (m, 10 H). STAGE D: 7-[[6-deoxy-5-C-methyl-4-0-methyl-3-0-(triethylsilyl)-alpha-L-lyxo-hexopyranosyl]oxy]-4-(diphenylme thoxy)-8-me thy1-2H-1-benzopyran-2 -one 26.6 g of imidazole and 70.15 ml of diisopropyl ethylamine are added to a solution cooled down to 0°C, containing 80 g of the product of the previous stage and 600 ml of dichloromethane. 33.5 ml of triethylsilyl chloride is added dropwise. Agitation is carried out for 1 hour at ambient temperature. The reaction medium is washed with a 1M aqueous solution of sodium dihydrogen phosphate, with water and with salt water. The reaction medium is dried over magnesium sulphate, filtered and concentrated. 97.58 g of product is collected which is purified by chromatography on silica, eluting with a dichloromethane acetone mixture (0.8 to 1%). 46.5 g of product is obtained. NMR 1H (300 MHz, CDCl3-d6, ppm) 0.60 (q, _H, J=_Hz) , 0.74 (q, _H, J=_Hz), 0.97 (t, _H, J=_Hz) , 1.00 (t, _H, J=_Hz) , 1.10 (s, 3H) , 1.32 (s, 3H) , 2.24 (s, 2H), 2.74 (s, 1H), 3.31 (d, 1H, J=_Hz), 3.54 (s, 3H), 4.07 (m, 1H), 4.29 (dd, 1H, J=_Hz), 5.50 (s, 1IH), 5.64 (d, 1H, J=_Hz, 6.35 (s, 1H) , 7.28 (d, 1H, J=_Hz) , 7.81 (d, 1H, J=_Hz) , 7.40 (m) . STAGE E: 7-[[6-deoxy-5-C-methyl-4-O-methyl-2-0-(tetrahydro-2H-pyran-2-yl)-3-0-(triethylsilyl)-alpha-L-lyxo-hexopyra nosyl]oxy]-4-(diphenylmethoxy)-8-methyl-2H-l-benzopyran-2-one 19 ml of dihydropyrane and 4 00 mg of APTS are added to a solution containing 67 g of the product of the previous stage and 1 1 of dichloromethane. Agitation is carried out for 4 0 minutes at ambient temperature, then 3 00 mg of APTS is added. After 30 minutes, 100 mg of APTS is added, then a further 100 mg of APTS. Agitation is carried out for 20 more minutes, then finely ground sodium hydrogen carbonate is introduced. Agitation is carried out for 10 minutes, the reaction medium is diluted with a hexane/ethyl acetate mixture (1-2) , washed with water and with salt water, then dried, filtered and the solvents are evaporated off. The product obtained is chromatographed eluting with a heptane/ethyl acetate mixture (4-1). 77.9 g of sought product is collected. NMR 1H (300 MHz, DMSO-d6, ppm) 0.64 (q, _H, J=_Hz), 0.73 (q, _H, J=_Hz), 0.95 to 1.32 (_H), 2.25 (s, _H), 2.27 (s, _H), 3.30 (d, _H, J=_Hz), 3.4 (d, _H, J=_ Hz), 3.50 (m, 2H), 3.93 (m, 2H), 3.53 (s, _H), 3.54 (s, _H), 4.04 to 4.15, 4.3 6 (dd, _H, J=_Hz), 4.94 (1), 4.96 (1), 5.50 (s1, _H) , 5.65 (s1), 6.37 (s, 1H) , 7.15 (d, _H, J=_Hz) , 7.19 (d, __H, J=_Hz) , 7.81 (m, 1H) , 7.30 to 7.44, 1.47 to 2.00. STAGE F: 7-[[6-deoxy-5-C-methyl-4-O-methyl-2-0-(tetrahydro-2H-pyran-2-yl)-3-O-trimethylsilyl)-alpha-L-lyxo-hexopyranosyl]oxy]-4-hydroxy-8-methyl-2H-l-benzopyran-2-one 15 g of the product of the previous stage in 150 ml of absolute ethanol is agitated in the presence of palladium on carbon (2 g, 10 %), under a hydrogen atmosphere. The catalyst is eliminated by filtration and the solvents are evaporated until dryness. 14.4 g of product is obtained. STAGF G: 3-acetyl-7- [ [6-deoxy-5-C-methyl-4-0-methyl-2-0-(tetrahydro-2H-pyran-2-yl)-3-0-(triethylsilyl)-alpha-L-lyxo-hexopyranosyl]oxy]-4-hydroxy-8-methyl-2H-l-benzopyran-2-one 6.52 g of dimethylaminopyridine is added to a solution containing 14.3 7 g of the product of the previous stage and 150 ml of dichloromethane. 2.72 ml of acetic anhydride is added dropwise. Agitation is carried out at ambient temperature under argon for 1 hour. The reaction medium is diluted with 200 ml of dichloromethane, washed with an aqueous solution of sodium dihydrogenen phosphate. The reaction medium is dried over magnesium sulphate, filtered and concentrated. 14.9 g of sought product is obtained. STAGF H: 3-acetyl-7- [ [6-deoxy-5-C-methyl-4-0-methyl-2-0-(tetrahydro-2H-pyran-2-yl)-alpha-L-lyxo-hexopyranosyl]oxy]-4-hydroxy-8-methyl-2H-1-benzopyran-2-one 27 ml of a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran, is introduced dropwise at 0°C into a solution containing 15.2 ml of the product of the previous stage in 250 ml of THF. Agitation is carried out under argon for 48 hours at ambient temperature. The reaction medium is diluted with an ethyl acetate/hexane mixture, washed with water and with salt water. The reaction medium is dried, filtered and concentrated to dryness. 13 g of a product is obtained which is triturated in pentane, the supernatant is eliminated and the operation is repeated several times. The product is kept in the refrigerator, then ground in the presence of pentane, the insoluble part is filtered, rinsed and dried. 6.99 g of sought product is obtained. NMR 1H (300 MHz, CDCl3-d6, ppm) 1.09 (s, 3H), 1.11 (s, 3H), 1.35 (s, 3H), 1.36 (s, 1H), 1.50 a 1.90 (m, 8), 2.23 (s, 3H), 2.24 (s, 3H), 2.76 (s, 3H), 3.28 (d, 1H, J=_Hz), 3.33 (d, 1H, J=_Hz), 3.63 (s, 3H), 3.64 (s, 3H), 3.54 (m), 3.97 (m), 4.07 (m), 4.20 to 4.30 (_, 2H), 4.59 (m, _H), 4.82 (m, _H), 5.63 (bs, _H), 5.85 (bs, _H), 7.20 (d, 1H, J=_Hz), 7.88 (m, _H). EXAMPLE 1: (2-propynyloxy)-carbamic acid 3"ester of 7-[[6-deoxy-5-C-me thy1-4-O-me thy1-alpha-L-lyxo-hexopyranosy1] oxy]-4-hydroxy-8-methyl-2 -oxo-2H-1-benzopyran-3 -carboxamide STAGE A: ethyl 7-[[6-deoxy-5-C-methyl-4-0-methyl-2-0-(tetrahydro-2H-pyran-2-yl)-alpha-L-lyxo-hexopyranosyl]oxy]-4-hydroxy-8-methyl-2-oxo-2H-l-benzopyran-3-carboxylate 3-(4-nitrophenylcarbonate) 4 g of the product of Preparation 1 is solubilized under argon in 80 ml of methylene chloride. 2.15 g of dimethylaminopyridine and at 0°C, 2 g of 4-nitro phenylchloroformate are added. Agitation is carried out for 1 hour at 0°C. The methylene chloride is evaporated off and the sought product is obtained. STAGE B: ethyl 7-[[6-deoxy-5-C-methyl-4-0-methyl-3-0-[[(2-propynyloxy)amino]carbonyl]-2-0-(tetrahydro-2H-pyran-2-yl) alpha-L-lyxo-hexopyranosyl]oxy]-4-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-carboxylate 1.215 g of O-propargylhydroxy1amine hydrochloride is solubilized in 4 0 ml of dimethylformamide, and dried over siliporite. At 0°C, 0.392 g of sodium hydride (with 50% oil) is added and agitation is carried out for one hour at this temperature. 4 ml of a solution of the product prepared in the previous stage in DMF containing and 94 0 mg of dimethylaminopyridine are introduced into this suspension at 0°C. Agitation is carried out for 1 hour at 0°C. The reaction medium is diluted with a hexane/ethyl acetate mixture (1-2) . The organic solution is washed with 400 ml of a 10% solution of sodium hydrogen sulphate, dried over sodium sulphate and evaporated to dryness. 7.87 g of crude sought product is obtained. STAGE C: (2-propynyloxy)-carbamic acid 3 '-ester of 7-[[6-deoxy-5-C-methyl-4-0-methyl-2-0-(tetrahydro-2H-pyran-2-yl) alpha-L-lyxo-hexopyranosyl]oxy]-4-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3 -carboxamide The product of the previous stage 2 g in 50 ml of tetrahydrofuran is solubilized in 50 ml of tetrahydrofuran. The solution obtained is saturated with ammonium hydroxide at 0°C for 10 minutes and agitated for 48 hours at ambient temperature. The reaction medium is diluted with 100 ml of a hexane/ethyl acetate mixture (1-1). The organic solution is washed with 100 ml of a 1M solution of sodium dihydrogen phosphate, then it is dried over magnesium sulphate and evaporated to dryness. 2 g of sought product is obtained. STAGE D: (2-propynyloxy) -carbamic acid 3 ' ester of 7-[[6-deoxy-5-C-me thy1-4-O-me thy1-alpha-L-lyxo-hexopyranosy1] oxy]-4-hydroxy-8-methyl-2-oxo-2H-l-benzopyran-3-carboxamide 2 g of the product of the previous stage and 200 mg of p-toluenesulphonic acid are solubilized in 20 ml of methanol. Agitation is carried out for 1 hour. The reaction medium is diluted with 100 ml of a hexane/ethyl acetate mixture (1-1). The reaction medium is washed with a saturated solution of sodium dihydrogen phosphate, dried and brought to dryness. 1.6 g of product is obtained which is purified eluting with an 8% methylene chloride/methanol mixture, followed by impasting with an ethyl ether/pentane mixture. 0.574 g of sought product is obtained. NMR 1H (3 00 MHz, DMSO-d6, ppm) 1.04 (s, 3H), 1.26 (s, 3H), 2.20 (s, 3H), 3.45, (s, 3H), 3.52 (d, 1H), 3.56 (m, 1H), 4.14 (m, 1H), 4.46 (m, 2H), 5.20 (m, 1H), 5.59 (bs, 1H), 5.77 (d, mobile 1H), 7.22 (d, 1Hz), 7.83 (d, 1H), 8.71 (m) and 8.96 (m) (mobile 2H's). EXAMPLE 2; (2-propynyloxy)-carbamic acid 3'-ester of 7-[(6-deoxy-5-C-me thy1-4-O-me thy1-alpha-L-lyxo-hexopyranosy1) oxy]-4-hydroxy-8-methyl-N-[2-(4-morpholinyl)ethyl] -2-oxo-2H-1-benzopyran-3 -carboxamide STAGE A: (2-propynyloxy)carbamic acid 3'-ester of 7-[[6-deoxy-5-C-methyl-4-0-methyl-2-0-(tetrahydro-2H-pyran-2-yl)-alpha-L-lyxo-hexopyranosyl]oxy]-4-hydroxy-8-methyl-N-[2-(4-morpholinyl)ethyl]-2-oxo-2H-l-benzopyran-3-carboxamide 7.5 ml of 2-(4-morpholino)ethylamine is introduced into a solution containing 1 g of the product of Stage B of Example 1 in 4 ml of tetrahydrofuran. Agitation is carried out for 1 day at ambient temperature. The reaction medium is diluted with 100 ml of hexane/ethyl acetate/ tetrahydrofuran (1-4-1). The reaction medium is washed with a saturated solution of sodium dihydrogen phosphate, dried over magnesium sulphate and evaporated to dryness. 1 g of sought product is obtained. STAGE B : (2-propynyloxy) -carbamic acid 3 '-ester of 7-[(6-deoxy-5-C-methyl-4-0-methyl-alpha-L-lyxo-hexopyranosyl) oxy]-4-hydroxy-8-methyl-N-[2-(4-morpholinyl)ethyl]-2-oxo-2H-1-benzopyran-3 -carboxamide 0.97 mmoles of the product of the previous stage are solubilized in 10 ml of methanol. 100 mg of p-toluenesulphonic acid is added. Agitation is carried out for 1 hour at ambient temperature. A further 80 mg of p-toluenesulphonic acid is added. Agitation is carried out for 3 hours. The reaction medium is diluted with 50 ml of a hexane/ethyl acetate mixture (1-3). The reaction medium is washed with 75 ml of a 1M solution of sodium dihydrogen phosphate, dried over magnesium sulphate and evaporated to dryness. The product is purified by chromatography on silica eluting with a methylene chloride/methanol mixture (91-9). The product obtained is impasted in an ethyl ether/pentane mixture. 0.150 g of sought product is obtained. NMR 1H (300 MHz, DMSO-d6, ppm) 1.03 (s, 3H), 1.27 (s, 3H), 2.21 (s, 3H), 2.50 (masked, 4H), 2.57 (t, 2H), 3.45 (s, 3H), from 3.40 to 3.69 (m, 4H), 4.13 (m, 1H), 4.47 (d, 2H, J=2.5 Hz), 5.20 (dd, 1H, J=3 and 10 Hz), 5.60 (d, 1H, J=2 Hz), 5.77 (d, 1H, J=5 Hz), 7.21 (d, 1H, J=9 Hz), 7.84 (d, 1H, J=9 Hz), 9.45 (t, 1H mobile), 10.72 (m, 1H mobile). EXAMPLE 3 ; (2-propynyloxy)-carbamic acid 3'-ester of 7-[[6-deoxy-5-C-methyl-4 -O-methy1-alpha-L-lyxo-hexopyranosy1] oxy]-4-hydroxy-3-[1-(methoxyimino)ethyl]-8-methyl-2H-1-benzopyran-2 -one £TAGE_A: 7-[6-deoxy-5-C-methyl-4-0-methyl-2-0-(tetrahydro-2H-pyran-2-yl)-alpha-L-lyxo-hexopyranosyl]oxy]-4-hydroxy-3-[1-(methoxyimino)ethyl]-8-methyl-2H-l-benzopyran-2-one A solution containing 1.2 g of the product of Preparation 2 is heated to 40°C in the presence of 0.597 g of potassium acetate and of 0.407 mg of 0- methylhydroxylamine hydrochloride. The reaction medium is agitated for one and a half hours at 40°C, diluted with an ethyl acetate/hexane mixture (4-1), washed with 150 ml of a solution of sodium hydrogen phosphate. The reaction medium is rinsed with water, dried, filtered and evaporated to dryness. STAGE B: 7-[[6-deoxy-5-C-methyl-4-O-methyl-2-O-(tetrahydro-2H-pyran-2-yl)-alpha-L-lyxo-hexopyranosyl]oxy]-4-hydroxy-3-[1-(methoxyimino)ethyl]-8-methyl-2H-benzopyran-2-one 3-(4-nitrophenylcarbonate) 0.390 g of dimethylaminopyridine is added to a solution containing 1.2 8 mmoles of the product of the previous stage and 12 ml of dichloromethane. 0.319 g of 4-nitrophenyl chloroformate is added. Agitation is carried out for 3 0 minutes at 0°C. The methyl chloride is evaporated off and the product obtained is dried. In this way 1.218 mmoles of sought product is obtained. STAGE C: (2-propynyloxy)-carbamic acid 3'-ester of 7-[[6-deoxy-5-C-methyl-4-0-methyl-2-0-(tetrahydro-2H-pyran-2-yl)alpha-L-lyxo-hexopyranosyl]oxy]-4-hydroxy-3-[1-(methoxy imino)ethyl]- 8-methyl-2H-1-benzopyran-2-one 0.240 g of sodium hydride (with 55% mineral oil) is added to a solution cooled down to 0°C of 0.655 g of O-propargylhydroxylamine hydrochloride in 6 ml of DMF. The reaction medium is agitated for 3 0 minutes at 0°C and poured into a solution containing 1.218 mmoles of the product of the previous stage and 6 ml of DMF in the presence of 0.150 g of dimethylaminopyridine. After one hour at 0°C, the reaction medium is poured into a 20% ethyl acetate/hexane mixture, washed with a 10% solution of sodium hydrogen sulphate, with water and with salt water. The reaction medium is dried and the solvents evaporated to dryness. 0.865 g of sought product is obtained. STAGE D: (2-propynyloxy)-carbamic acid 3'-ester of 7-[[6-deoxy-5-C-methyl-4-0-methyl-alpha-L-lyxo-hexopyranosyl] oxy]-4-hydroxy-3-[1-(methoxyimino)ethyl]-8-methyl-2H-1-benzopyran-2-one 150 mg of APTS is added to a solution containing 1.218 mmoles of the product of the previous stage and 12 ml of methanol. Agitation is carried out for one hour at ambient temperature. The reaction medium is diluted with an ethyl acetate/hexane mixture (1-1) and washed with a 1M aqueous solution of sodium dihydrogen phosphate, then with salt water. The organic phase is dried over magnesium sulphate. The solvents are evaporated until dryness. The product obtained is chromatographed eluting with a dichloromethane/acetone mixture (85-15), and 0.394 g of product is collected which is redissolved in ether and precipitated with pentane. The insoluble part is isolated by filtration and dried under reduced pressure. 0.380 g of sought product is obtained. EXAMPLE 4 : (2-propynyloxy) -carbamic acid 3'-ester of 7-[(6-deoxy-5-C-methyl-4-O-methyl-alpha-L-lyxo-hexopyranosyl) oxy]-3-[1-(ethoxyimino)ethyl]-4-hydroxy-8-methyl-2H-l-benzopyran-2-one By operating as previously, the sought product was obtained. NMR CDC13 ppm 1.17 (s) - 1.38 (s): 2 CH3 Gem; 1.38 (t): CH3CH20; 1.61 (s): mobile 4, 2.25 (s) - 2.53 (s): 2CH3-C-; 2.57 (t): J=2.5 h-C C-; 2.64 (bs) OH-CH; 3.54 (s): OCH3; 3.61 (d): J=9.5 H4 rex; 4.23 (q) CH3-CH2-0 slightly defective; 4.43 (bs): H2eq; 4.57 (d): 2H 0CH2-C CH; 5.46 (dd): J=2.5 and 9.5 H3 ox; 5.61 (d): J=2.5 H1 eq; 7.12 (d): H'6; 7.77 (d): H'5; mobile H's 7.78: 14.15 and 15.11 Absorptions along the spectrum 2.05 (acetone), 4.13, 4,75-4,60-15.67. EXAMPLE 5; 8-hydroxy-7-[4-hydroxy-3-[1-(methoxyimino)ethyl]- 8-methyl-2 -oxo-2H-1-benzopyran-7-yl]-10-methoxy-6- oxaspiro[4,5]decan-9-yl [7R-(7.alpha.,8.beta.,9.beta., 10.alpha.)]-(2-propynyloxy)-carbamate The preparation of this product and that of the starting products used can be illustrated as follows: (Formula Removed) Preparation 3; [8R-(8.alpha.,9.alpha,10.beta)]-10-methoxy-6-oxaspiro[4.5]decane-7.8,9-triol STAGE A:[4S-[4.alpha.,5.alpha.(S*)]]-2,2-dimethyl-5-[(1-hydroxycyclopentyDmethoxymethyl]-1,3-dioxolane-4-methanol 20 ml of a solution of dibromobutane (106 ml of dibromobutane in 200 ml of THF), is introduced into a mixture containing 43 g of magnesium, 100 ml of THF and an iodine crystal. The reaction medium is placed under ultrasound. 1.7 1 of THF is added. The remainder of the dibrominated solution is added. Agitation is maintained for 2 hours 30 minutes. A solution containing 80.37 g of 2-0- methyl-3,4-0-(1-methylethylidene)-L-arabinonic acid delta-lactone and 1 litre of THF is added at 17°C. Agitation is carried out for 4.5 hours at ambient temperature. The reaction medium is cooled down to 0°C, and a saturated solution of ammonium chloride is added. The reaction medium is decanted, the organic phase is removed and extraction is carried out with a solution of ethyl acetate with 20% heptane, followed by washing, drying and evaporating to dryness. 111.85 g of sought product is obtained. S1AGE—B: [3'As-(3'a.alpha.,7'.alpha,7'a.beta.)]-7'-methoxy-dihydro-spiro[cyclopentane-1.6 ' -[6H]-1,3-dioxolo[4,5-c]pyran]-4'(3aH)-one 221 g of PyS03 is added to a solution containing 111 g of the product prepared in Stage A and a mixture of one litre of methylene chloride, 1 litre of DMSO, 0.607 1 of triethylamine. Agitation is carried out for 2 hours at ambient temperature. The reaction medium is poured into an aqueous solution of sodium acid phosphate, extracted with an ethyl acetate, heptane mixture (1-1), dried, filtered and evaporated to dryness. 57.7 g of sought product is obtained. STAGE C: [8R- (8 .alpha., 9 .alpha, 10 .beta) ] -10-methoxy-6-oxaspiro[4,5]decane-7.8,9-triol 157 ml of a 1.5 M solution of dibutylaluminium hydride in toluene is added at -5°C to a solution containing 56 g of the product of the previous stage and 3 00 ml of THF. Agitation is carried out at -3°C for 1 hour. 1 litre of a 1 M solution of sodium and potassium double tartrate is added. Agitation is carried out for 15 minutes at ambient temperature. The reaction medium is extracted with an ethyl acetate-heptane mixture 1-1. The extracts are washed with water, with salt water, dried and evaporated to dryness. The residue obtained is agitated at 70°C in the presence of 150 ml of a 0.1 N solution of sulphuric acid and 150 ml of water for 2.5 hours, followed by cooling down to ambient temperature. Barium carbonate is added and agitation is carried out for 1 hour at ambient temperature, followed by filtering and evaporating to dryness. 49 g of sought product is obtained. EXAMPLE 5: 8-hydroxy-7-[4-hydroxy-3-[1-methoxyimino)ethyl]-8-methyl-2-oxo-2H-1-benzopyran-7-yl]-10-methoxy-6-oxaspiro[4,5]decan-9-yl [7R-(.alpha.,8.beta.,9.beta., 10.alpha.)]-(2-propynyloxy)-carbamate STAGE A; [7R-(7.alpha.,8.beta.,9.beta.,10.alpha.) ]-7- [ (8,9-dihydroxy-10-methoxy-6-oxaspiro[4,5]decan-7-yl)oxy]-4-(diphenylmethoxy)- 8-methyl-2H-1-benzopyran-2 -one 45.30 g of DIAD is added dropwise at 0°C to a mixture of 49 g of the product of Preparation 3, 73 g of the product of Stage B of Preparation 2 namely 4-(diphenylmethoxy)-7-hydroxy-8-methyl-2H-1-benzopyran-2-one and 59 g of triphenylphosphine. Agitation is carried out for 1.5 hours at ambient temperature. 1 equivalent of triphenylphosphine and of DIAD are added at 0°C. The solvents are evaporated off, the residue is taken up in ether and the sought product is obtained. STAGE B: [7R-(7.alpha.,8.beta.,9.beta.,10.alpha.) 1-4-(diphenylmethoxy)-7-[[8-hidroxy-10-methoxy-9- [(triethylsily)oxy]-6-oxaspiro[4,5]decan-7-yl)oxy]-8-methyl-2H-1-benzopyran-2 -one 15.21 g of imidazole, 40.1 ml of diisopropylamine and 18.75 g of triethylsilane chloride are added at 0°C to a solution containing 48 g of the product of the previous stage and 400 ml of methylene chloride. The reaction medium is agitated for 1 hour at 0°C, washed with a 1 M solution of sodium acid phosphate and rinsed with water. The reaction medium is dried. The product obtained is chromatographed on silica eluting with a methylene chloride/acetone mixture 99-1 then with a toluene tertbutylmethylether mixture. 28.37 g of sought product is obtained. STAGE C: [7R-(7.alpha.,8.beta.,9.beta.,10.alpha.) ] -4-(diphenylmethoxy)-7- [ [10-methoxy-8-[(tetrahydro-2H-pyran-2-yl)oxy] -9-[(triethylsily)oxy]-6-oxaspiro[4,5]decan-7-yl)oxy]-8-methyl-2H-1-benzopyran-2-one 7.57 ml of 3,4-dihydropyran and 400 mg of paratoluene sulphonic acid are added to a solution/Containing 28.1 g of the product of the previous stage and 250 ml of dichloromethane. Agitation is carried out for 1 hour at ambient temperature. Bicarbonate of soda is added and agitation is carried out for 20 minutes at ambient temperature. The reaction medium is washed with water, and the organic phases dried over sodium sulphate. The product obtained is chromatographed on silica eluting with a 4.1 heptane-ethyl acetate mixture. 16.81 g of sought product is obtained. STAGE D: [7R-(7.alpha.,8.beta.,9.beta.,10.alpha.)]-4--hydroxy)-7-[[10-methoxy-8-[(tetrahydro-2H-pyran-2-yl)oxy]-9-[(triethylsily)oxy]-6-oxaspiro[4,5]decan-7-yl)oxy]-8-methyl-2H-l-benzopyran-2-one A solution of 16.19 g of the product of the previous stage, 150 ml of THF, are agitated under a hydrogen atmosphere in the presence of 810 mg of palladium on carbon. The reaction medium is filtered and 15.1 g of expected product is obtained. STAGE-E: [7R-(7.alpha.,8.beta., 9.beta.,10.alpha.)]-3-acetyl-4-hydroxy)-7-[[10-methoxy-8-[(tetrahydro-2H-pyran-2-yl)oxy]-9-[(triethylsily)oxy]-6-oxaspiro[4.5]decan-7-yl)oxy]-8-methyl-2H-l-benzopyran-2-one 2.28 ml of acetic anhydride is added to a mixture containing 13.8 g of the product of the previous stage and 150 ml of methylene chloride and 5.94 g of DMAP. Agitation is carried out for one hour at ambient temperature. The reaction medium is treated with a molar solution of sodium acid phosphate, extraction is carried out using methylene chloride followed by washing with water and drying. 16.21 g of sought product is obtained used as it is in the following stage. STAGEF: [7R-(7.alpha.,8.beta.,9.beta.,10.alpha.)]-3-acetyl-4-hydroxy-7-[[9-hydroxy-10-methoxy-8-[(tetrahydro-2H-pyran-2-yl)oxy]-6-oxaspiro[4.5]decan-7-yl)oxy]-8-methyl-2H-1-benzopyran-2-one 1.5 equivalents of a 1M solution of tetrabutylammonium fluoride in THF are added at 0°C to a solution containing the product of the previous stage and 2 00 ml of THF. The reaction medium is maintained under agitation at ambient temperature for 15 hours. The reaction medium is poured into a heptane-ethyl acetate mixture 30-70, washed with water, dried and filtered. A product is obtained which is used as it is in the following stage. STAGE G: [7R-(7.alpha.,8.beta.,9.beta.,10.alpha.)] -4-hydroxy-7-[[9-hydroxy-10-methoxy-8-[(tetrahydro-2H-pyran-2-yl)oxy]-6-oxaspiro[4,5]decan-7-yl)oxy]-3-[1-(methoxyimino)ethyl]-8-methyl-2H-l-benzopyran-2-one 4.6 g of potassium acetate and 3.12 g of O-methylhydroxylamine hydrochloride are added to a solution containing 18.69 mmoles of the product of the previous stage and 100 ml of ethanol. Agitation is carried out for 1.5 hour at ambient temperature. The reaction medium is poured into a 1M solution of sodium acid phosphate, followed by extraction with a heptane/ethyl acetate mixture 30-70. The extracts are washed with water, dried and evaporated to dryness. The product obtained is chromatographed with a heptane-ethyl acetate mixture (1:1). 6.54 g of sought product is obtained. STAGE H: 8-hydroxy-7-[4-hydroxy 3-[1-methoxyimino)ethyl]-8-methyl-2-oxo-2H-l-benzopyran-7-yl]-10-methoxy-6-oxaspiro-[4.5]decan-9-yl [7R.(7.alpha.,8.beta.,9.beta., 10.alpha.)]-(2-propynyloxy)-carbamate 1) 3.70 g of DMAP and 3.05 g of para-nitrobenzene chloroformate are introduced at 0°C to a solution containing 6.37 g of the product of the previous stage and 70 ml of dichloromethane. Agitation is carried out for 1 hour at 0°C. 2) 2.3 g of sodium hydride at 0°C is added to a solution containing 6.2 6 g of propargylhydroxylamine hydrochloride and 50 ml of DMF. Agitation is carried out for 1 hour at 0°C. Solution (1) is concentrated to dryness. The residue obtained is dissolved in 50 ml of DMF. 1.42 g of DMAP is added. Solution (2) is added at 0°C to the solution obtained in this way. Agitation is carried out for 1 hour at 0°C. The reaction medium is treated with sodium acid phosphate, washed with water, dried and concentrated to dryness. The residue obtained is dissolved in 100 ml of methanol. 2.1 g of APTS is added and agitation is carried out at ambient temperature. The product obtained is chromatographed eluting with toluene and then with a toluene-isopropyl ether mixture 92-8. The product is dispersed under ultrasound in an isopropyl ether-pentane mixture. The sought product is obtained. NMR spectrum: CDC13 ppm 1.3 0 to 2.00 CH2 cycle 2.20(s) C6H5-Me 2.50(s) N=C-Me 2.56(t) 0-CH2-C(CH 4.57(d) t 3.55(s) C-OMe 3.65(d,J=8) H4ax 4.00(s) =N-OMe 4.38(bs) H2eq 5.37(dd) H3ax 5.51(d) Hleq 7.00 (d) H6' 7.66 (d) H5' 8.19(bs) NH Preparation 4 STAGE A (Formula Removed) 20.4 g of 2-0-methyl-3,4-0-(l-methylethyledene)L-arabinose is dissolved under an argon atmosphere in 200 ml of tetrahydrofuran. 200 ml of a 2M solution of allylmagnesium bromide in tetrahydrofuran is added at 0°C under argon. The solution is agitated for 1 hour at 0°C. The reaction medium is cooled down to -15°C and is diluted with 100 ml of heptane. In order to neutralize the excess magnesium, 300 ml of a 10% aqueous solution of sodium hydrogen sulphate is added dropwise. The organic phase is separated and the aqueous phase is extracted with a heptane 1/ethyl acetate 2 mixture. The organic phases are collected, dried over magnesium sulphate and evaporated to dryness. 22.96 g of sought product is obtained. Yield:94 % STAGE B: 22.96 g of the product of the previous stage is solubilized under an argon atmosphere in 175 ml of dimethylformamide. 14.88 g of imidazole is added then 23.31 ml of diphenylterbuthylsilyl chloride is added dropwise at 0°C under argon over 30 minutes. The solution is agitated for 30 minutes at 0°C. The reaction medium is diluted with 400 ml of a heptane 1/ethyl acetate 2 mixture. The organic phase is washed with twice 200 ml of an aqueous solution of 1 molar sodium dihydrogen phosphate, dried over magnesium sulphate and evaporated to dryness. 45 g of resin product is obtained which is purified by chromatography on silica eluting with a heptane 4/ethyl acetate 1 mixture. 3 9.5 g of sought product is obtained. Yield: 85% STAGE C: (Formula Removed) 25.1 g of Pyridinium Chlorochromate is suspended in 200 ml of methylene chloride. 53.8 g of 4A molecular sieve is then added. 3 9.5 g of the product of the previous stage in solution in 100 ml of methylene chloride is then introduced into this suspension in one go. Agitation is carried out for 3 hours. The suspension is filtered, and eluted with a methylene chloride 3% methanol mixture. The filtrate is evaporated to dryness. The residue obtained (35 g) is filtered on silica eluting with a heptane 4/ethyl acetate 1 mixture. 3 2.9 g of sought product is obtained. Yield: 87% SIAGE H: (Formula Removed) 32.5 g of the product of the previous stage is dissolved in 250 ml of tetrahydrofuran. 60 ml of a 3 molar solution of methylmagnesium bromide in ether is added dropwise under argon at -5°C. Agitation is carried out for 1 hour at ambient temperature. At 0°C, the excess magnesium is neutralized with a 10% aqueous solution of sodium hydrogen sulphate. 200 ml of a heptane l/ethyl acetate 2 mixture is added. The organic phase is washed with 200 ml of a 1 molar aqueous solution of sodium dihydrogen phosphate, dried over magnesium sulphate and evaporated to dryness. The product obtained is impasted in 200 ml of pentane/ether. 16.9 g of sought product is obtained. Yield: 64% (Formula Removed) 16.9 g of the product of the previous stage is dissolved in 150 ml of tetrahydrofuran. 68 ml of a 1 molar solution of tetrabutylammonium fluoride in tetrahydrofuran is added dropwise under argon at 0°C. Agitation is carried out for 3 0 minutes at ambient temperature. 200 ml of a heptane 1/ethyl acetate 2 mixture is added. The organic phase is washed with 200 ml of a 1 molar aqueous solution of sodium dihydrogen phosphate, dried over magnesium sulphate and evaporated to dryness. The crude product is purified by chromatography on silica eluting with a methylene chloride 95/methanol 5 mixture. 10.1 g of sought product is obtained. STAGE F (Formula Removed) 10.15 g of the product of the previous stage is solubilized in 103 ml of methylene chloride. 55ml of triethylamine and 103 ml of dimethylsulphoxide stored on a molecular sieve is added under argon, at ambient temperature. The solution is cooled down to approximately 5°C with an ice-water bath and 19.77 g of pyridine sulphur trioxide is added by fractions, without the temperature exceeding 15°C. Agitation is carried out for 1 hour. The reaction medium is poured into 1 litre of a 1 molar aqueous solution of sodium dihydrogen phosphate, the aqueous phase is extracted twice with a heptane l/ethyl acetate 2 mixture. The organic phase is washed with water, dried over magnesium sulphate and evaporated to dryness. The crystallized crude product is impasted in pentane. The product obtained is impasted in pentane. 6.8 g of sought product is obtained. Yield: 68% STAGE G: (Formula Removed) 5.3 g of the product of the previous stage is solubilized in 30 ml of tetrahydrofuran. 13.85 ml of DIBAL is added under argon, at -0°C. After agitation for 1 hour 30 minutes at 0°C, the reaction is terminated. The reaction medium is poured into 100 ml of a 1M solution of sodium and potassium double tartrate; the aqueous phase is extracted with a heptane 1/ethyl acetate 2 mixture. The organic phase is washed with 150 ml of a 10% aqueous solution of sodium hydrogen sulphate, dried over magnesium sulphate and evaporated to dryness. 5.5 g of sought product is obtained. Yield: Quantitative (Formula Removed) STAGE H 5.5 g of the product of the previous stage is emulsified in 32 ml of a 0.05 N solution of sulphuric acid. After heating at 70°C for 1 hour 30 minutes, the reaction is terminated. The product is allowed to return to ambient temperature and neutralized with 0.6 g of barium carbonate. The suspension is agitated for one hour at ambient temperature (pH=7), then filtered and evaporated to dryness. In order to dry it, the product is entrained twice with toluene. The reaction medium is dried and 4.4 g of sought product is obtained. Yield: 96% EXAMPLE 6; 7-[[6-deoxy-4-0-methyl-5-C-(2-propenyl)-3-0-[[(2- propynyloxy)amino]carbonyl]-.beta.-D-gulopyranosyl]oxy]-4- hydroxy-8-methyl-3- [1-[(2-propynyloxy)imino]ethyl]-2H-1- benzopyran-2-one and 7-[[6-deoxy-4-0-methyl-5-C-(2-propenyl)-3-0-[[(2- propynyloxy)amino]carbonyl]-.beta.-D-gulopyranosyl]oxy]-4- hydroxy-3-[1-(methoxyimino)ethyl]- 8-methyl-2H-1-benzopyran- 2-one STAGE A (Formula Removed) 4.4 g of the product of Preparation 4 is solubilized in 100 ml of methylene chloride. 7.33 g of coumarine 7-hydroxy-3- [(methoxyimino)methyl]-8-methyl-4-(2-propenyloxy)-2H-1-benzopyran-2-one prepared as indicated in Preparation 8 of WO 9747364 and 6.29 g of triphenylphosphine are added at ambient temperature, under argon. The suspension is cooled down to 0°C. 3.73 ml of DEAD is added dropwise. The suspension is agitated for 1 hour at ambient temperature. 6.06 g of triphenylphosphine is again added followed by 3.11 ml of DEAD at 0°C. After agitation for 1 hour at ambient temperature, 50 ml of pentane is added in order to precipitate the reduced DEAD. The suspension is filtered, the filtrate is evaporated to dryness and purified on silica with the eluant mixture toluene with 3% isopropyl alcohol (the elution is finished with 6%). 7.1 g of product is obtained. The product is filtered on silica 60 eluting with an ether/heptane mixture then with ether. 6.13 g of sought product is obtained. STAGE B (Formula Removed) 6 g of the product of the previous stage is solubilized in 75 ml of tetrahydrofuran. 3.86 g of carbonyldiimidazole is added and the reaction is heated for 1 hour under reflux. The reaction medium is diluted with 100 ml of a heptane l/ethyl acetate 2 mixture. The organic phase is washed with a 10% aqueous solution of sodium hydrogen sulphate, dried over magnesium sulphate and evaporated to dryness. 4.94 g of sought product is obtained. STAGE C (Formula Removed) 4.94 g of the product of the previous stage is solubilized in 120 ml of tetrahydrofuran. 8.44 ml of diisopropylamine at 0°C, and 1.05 g of palladium tetrakistriphenylphosphine are added. Agitation is carried out for 20 minutes at 0°C. The reaction medium is diluted with 50 ml of a heptane l/ethyl acetate 2 mixture. The organic phase is washed with a 10% aqueous solution of sodium hydrogen sulphate, dried over magnesium sulphate and evaporated to dryness. 5.5 g of crude product is obtained which is purified on silica eluting with the mixture methylene chloride with 2% acetone, 3.1 g of sought product is obtained. (Formula Removed) 0.65 g of the product of the previous stage is solubilized in 6.5 ml of pyridine dried over potash. 1.5 g of propargylhydroxylamine hydrochloride and 0.149 of lithium perchlorate are added at ambient temperature. Agitation is carried out at ambient temperature for 4 8 hours. The reaction medium is diluted with a heptane 1/ethyl acetate 2 mixture and the organic phase is washed with a 10% solution of sodium hydrogen sulphate, then dried over magnesium sulphate. 1.8 g of product is obtained which is purified by chromatography on silica eluting with the eluant mixture methylene chloride 8 0/terbutylmethylether 20. 200 mg of sought product is obtained isomer in 2 and 50 0 mg isomer in 3. (Formula Removed) 0.5 g of the product of the previous stage isomer in 2 is solubilized under an argon atmosphere in 10 ml of methylene chloride. 100 µl of DBU is added. Agitation is carried out for 24 hours at ambient temperature. The reaction medium is diluted in 50 ml of a heptane l/ethyl acetate 3 mixture and the organic phase is washed with a 1M solution of sodium dihydrogen sulphate, dried over magnesium sulphate and evaporated to dryness. The product previously obtained is dissolved in 5 ml of ethanol. 0.72 g of methylhydroxylamine hydrochloride and 0.94 g of sodium acetate are added at ambient temperature. The reaction medium is agitated for 5 hours at ambient temperature. The reaction medium is diluted in 50 ml of a heptane l/ethyl acetate 3 mixture and the organic phase is washed with a 1M solution of sodium dihydrogen sulphate, dried over magnesium sulphate and evaporated to dryness. 0.45 g of crude product is obtained which is purified by chromatography on silica with the eluant mixture methylene chloride 80/20 terbutylmethylether 20. 10 0 mg of sought product is obtained. Preparation 5 STAGE A: (Formula Removed) 20.4 g of 2-0-methyl-3,4-0(1-methylethylidene)L-arabinose is solubilized under argon in 250 ml of tetrahydrofuran. 100 ml of a 1M solution of vinylmagnesium bromide in tetrahydrofuran then 200 ml of a 1.7M solution of magnesium chloride in tetrahydrofuran (0.34 moles) are added at 0°C under argon. The solution is agitated for 1 hour at ambient temperature. The reaction medium is cooled down to -15°C and is diluted with 100 ml of heptane. In order to neutralize the excess magnesium, 300 ml of a 20% mixture of a 1 molar aqueous solution of sodium dihydrogen phosphate in tetrahydrofuran is added dropwise. The magnesium salts precipitate. 200 ml of a heptane l/ethyl acetate 2 mixture and 150 ml of a 10% solution of sodium hydrogen sulphate are added. The organic solution is dried over magnesium sulphate and evaporated until dryness. 19.3 g of sought product is obtained. Yield: 83% STAGE B (Formula Removed) 19.3 g of the product of the previous stage is solubilized in 150 ml of dimethylformamide. 10.8 g of imidazole is added followed by 23.4 ml of diphenylterbutylsilyl chloride at 0°C under argon, dropwise over 3 0 minutes. The solution is agitated for 30 minutes at 0°C. The reaction medium is diluted with 400 ml of a heptane l/ethyl acetate 2 mixture. The organic phase is washed with a 1M aqueous solution of sodium dihydrogen phosphate, dried over magnesium sulphate and evaporated to dryness. 30.2 g of resin product is obtained which is purified by chromatography on silica eluting with a heptane 4: ethyl acetate 1 mixture. 3 0.2 g of sought product is obtained. Yield: 77% SIAGE C: (Formula Removed) 19.1 g of pyridinium chlorochromate is solubilized in 250 ml of methylene chloride. 40 g of 4A molecular sieve is then added. 28.19 g of the product of the previous stage in solution in 100 ml of methylene chloride is introduced in one go into this suspension. After agitation for 4 hours at ambient temperature, the reaction is finished. Filtration is carried out. The filtrate is evaporated to dryness. The product obtained is chromatographed on silica eluting with a heptane/ethyl acetate 6-1 mixture. 10.5 g of sought product is obtained. Yield 36 %. STAGE D (Formula Removed) 10 g of the product of the previous stage is solubilized in 100 ml of tetrahydrofuran. 14 ml of a 3 molar solution of methylmagnesium bromide in ether is added dropwise under argon, at -5°C. Agitation is carried out for 30 minutes at 0°C. At 0°C, the excess magnesium is neutralized with a 10% aqueous solution of sodium hydrogen sulphate. 200 ml of a heptane 1/ethyl acetate 2 mixture is added. The organic phase is washed with 200 ml of a 1 molar aqueous solution of sodium dihydrogen phosphate, dried over magnesium sulphate and evaporated to dryness. The crude product is purified on silica eluting with a heptane 4/ethyl acetate 1 mixture. The product obtained is impasted in pentane. 2.76 g of sought product is obtained. Yield 27% STAGE E (Formula Removed) 2.79 g of the product of the previous stage is solubilized in 15 ml of tetrahydrofuran. 11.8 ml of a 1 molar solution of tetrabutylammonium fluoride in tetrahydrofuran is added dropwise under argon, at 0°C. Agitation is carried out for 1 hour at ambient temperature. 200 ml of a heptane 1/ethyl acetate 2 mixture is added. The organic phase is washed with 200 ml of a 1 molar aqueous solution of sodium dihydrogen phosphate, dried over magnesium sulphate and evaporated to dryness. The crude product is purified by chromatography on silica eluting with a methylene chloride with 5% methanol mixture. 1.2 g of sought product is obtained. Yield: 86% STAGE F: (Formula Removed) 1.2 g of the product of the previous stage is solubilized in 12.5 ml of methylene chloride. 6.67 ml of triethylamine and 12.5 ml of dimethylsulphoxide stored on a molecular sieve is added under argon, at ambient temperature. The solution is cooled down to approximately 5°C with an ice-water bath and 2.39 g of pyridine sulphurtrioxide is added by fractions without the temperature exceeding 15°C. After agitation for 1 hour at ambient temperature, the reaction is terminated. Agitation is carried out for 1 hour at ambient temperature. The reaction medium is poured into 100 ml of a 1 molar aqueous solution of sodium dihydrogen phosphate, the aqueous phase is extracted twice with a heptane l/ethyl acetate 2 mixture. The organic phase is washed with water, dried over magnesium sulphate and evaporated to dryness. The product obtained is impasted in pentane. 0.75 g of sought product is obtained. Yield: 59% STAGE G: (Formula Removed) 0.73 g of the product of the previous stage is solubilized in 3 0 ml of tetrahydrofuran. 2.5 ml of a 1.5M solution of DIBAL in toluene is added under argon, at -6°C. Agitation is carried out 1 hour 30 minutes at -6°C. The reaction medium is poured into a 1M solution of sodium and potassium double tartrate; the aqueous phase is extracted with a heptane l/ethyl acetate 2 mixture. The organic phase is washed with a 10% aqueous solution of sodium hydrogen sulphate, dried over magnesium sulphate and evaporated to dryness. The product obtained is impasted in pentane. 0.95 g of sought product is obtained. Quantitative yield STAGE H (Formula Removed) 0.9 g of the product of the previous stage is emulsified in 5 ml of a 0.05N solution of sulphuric acid. After heating at 70°C for 1 hour, the reaction is terminated. The reaction medium is allowed to return to ambient temperature then extracted with pentane, and the aqueous phase is neutralized with 0.1 g of barium carbonate. The suspension is agitated for one hour at ambient temperature (pH=7), then filtered and evaporated to dryness. In order to dry it, the product is entrained twice with toluene, then solubilized in methylene chloride. The solution is dried over magnesium sulphate and evaporated to dryness. 0.5 g of sought product is obtained. Yield 86% EXAMPLE 7: 7-[[6-deoxy-5-C-ethenyl-4-0-methyl-3-O-[[(2-propynyloxy)amino]carbonyl]-.beta.-D-gulopyranosyl]oxy] -4-hydroxy-3-[1-(methoxymino)ethyl]-8-methyl-2H-l-benzopyran-2-one STAGE A (Formula Removed) 0.5 g of the product of Preparation 5 is solubilized in 17 ml of methylene chloride. 0.89 g of coumarine and 0.76 g of triphenylphosphine are added at ambient temperature, under argon. The suspension is cooled down to 0°C, and 0.45 ml of DEAD is added dropwise. The suspension is agitated for 1 hour at ambient temperature. A further 0.63 g of triphenylphosphine is added followed by 0.37 ml of DEAD at 0°C. A yellow solution is obtained. After agitation for 1 hour at ambient temperature, 10 ml of pentane is added in order to precipitate the reduced DEAD. The suspension is filtered, the filtrate is evaporated to dryness and purified by chromatography on silica with the eluant mixture toluene 97/isopropyl alcohol 3 (the elution is finished with 6%). The product obtained in a mixture is then filtered on silica 60 eluting with a heptane 1/ether 2 mixture then ether. 0.55 g of white crystals is obtained. Yield: 47% STAGE R (Formula Removed) 0.55 g of the product of the previous stage is solubilized in 7 ml of tetrahydrofuran. 0.3 64 g of carbonyl-diimidazole is added and the reaction medium is heated under reflux for 1 hour. The reaction medium is diluted with 4 0 ml of a heptane 1/ethyl acetate 2 mixture. The organic phase is washed with 5 0 ml of a 10% aqueous solution of sodium hydrogen sulphate, dried over magnesium sulphate and evaporated to dryness. 0.5 g of sought product is obtained. Yield: 88% STAGE C: (Formula Removed) 0.5 g of the product of the previous stage is solubilized in 12 ml of tetrahydrofuran. 0.82 ml of diisopropylamine is added followed by 0.11 g of palladium tetrakistriphenyl phosphine (0.1 equivalent) at 0°C. Agitation is carried out for 20 minutes at 0°C. The reaction medium is diluted with 50 ml of a heptane l/ethyl acetate 2 mixture. The organic phase is washed with 50 ml of a 10% aqueous solution of sodium hydrogen sulphate, dried over magnesium sulphate and evaporated to dryness. 0.58 g of crude product is obtained which is purified by chromatography on silica eluting with a heptane 3/ethyl acetate 1 mixture. 0.257 g of sought product is obtained. Yield: 57% STAGE D: (Formula Removed) 0.257 g of the product of the previous stage is solubilized in 2.5 ml of pyridine dried over potash. 0.58 g of propargylhydroxylamine hydrochloride and 0.057 g of lithium perchlorate are added at ambient temperature. The reaction medium is agitated for 48 hours at ambient temperature. The reaction medium is diluted with a heptane l/ethyl acetate 2 mixture and the organic phase is washed with a 10% solution of sodium hydrogen sulphate, and dried over magnesium sulphate. 0.28 g of sought product is obtained. The crude product obtained is dissolved in 5 ml of ethanol, then 0.45 g of methylhydroxylamine hydrochloride and 0.5 8 g of sodium acetate are added. The reaction medium is agitated for 5 hours at ambient temperature. The reaction medium is diluted with a heptane l/ethyl acetate 2 mixture and the organic phase is washed with a 1M solution of sodium dihydrogen phosphate, dried over magnesium sulphate and evaporated to dryness. 0.3 g of crude product is obtained which is purified by chromatography on silica eluting with a methylene chloride 80/ethyl acetate 19/acetic acid 1 mixture. 0.090 g of sought product is obtained. Yield: 31% Preparation 6 (Formula Removed) 10.5 g is solubilized in 110 ml of tetrahydrofuran. 329 ml of a 0.135M solution of zinc tetraborohydride in ether is added under argon, at -6°C. The reaction medium is left under agitation for 30 minutes without an ice bath, the reaction is then terminated. A 1 molar solution of sodium dihydrogen phosphate is added. The aqueous phase is extracted with a heptane 1/ethyl acetate 2 mixture. The organic phase is dried over magnesium sulphate and evaporated to dryness. 10.5 g of sought product is obtained which is purified by chromatography eluting with a heptane 4/ethyl acetate 1 mixture. 8.75 g of sought product is obtained. Yield: 83% STAGE B (Formula Removed) 8.75 g of the product of the previous stage is solubilized in 100 ml of tetrahydrofuran. 37 ml of a 1 molar solution of tetrabutylammonium fluoride in tetrahydrofuran (0.037 mole) is added under argon, at 0°C. After agitation for 30 minutes at 0°C, 200 ml of a heptane l/ethyl acetate 2 mixture is added. The organic phase is washed with 200 ml of a 1 molar aqueous solution of sodium dihydrogen phosphate, dried over magnesium sulphate and evaporated to dryness. The crude product (10.5 g) is purified by chromatography on silica eluting with a methylene chloride mixture with 20% acetone. 3.6 g of sought product is obtained. Yield: 78% STAGE C (Formula Removed) 3.57 g of the product of the previous stage is placed in 38 ml of methylene chloride. 20.5 ml of triethylamine and 38 ml of dimethylsulphoxide (fluka) is added under argon, at ambient temperature. The solution is cooled down to approximately 5°C and 7.6 g of pyridine sulphur trioxide is added without the temperature exceeding 15°C. Agitation is carried out for 2 hours. The reaction medium is poured into 500 ml of a 1 molar aqueous solution of sodium dihydrogen phosphate, and the aqueous phase is extracted twice with a heptane 1/ethyl acetate 2 mixture. The organic phase is washed twice with 50 0 ml of water, dried over magnesium sulphate and evaporated to dryness. The crystallized crude product is impasted in pentane. 1.92 g of sought product is obtained. Yield: 56% STAGE D (Formula Removed) 1.9 g of the product of the previous stage is solubilized in 10 ml of tetrahydrofuran. 6.66 ml of a 1.5M solution of DIBAL in toluene is added under argon, at 0°C. Agitation is carried out for 1 hour 3 0 minutes. The reaction medium is poured into 100 ml of a 1M solution of sodium and potassium double tartrate; the aqueous phase is extracted with a heptane l/ethyl acetate 2 mixture. The organic phase is washed with 150 ml of a 10% aqueous solution of sodium hydrogen sulphate, dried over magnesium sulphate and evaporated to dryness. 1.9 g of sought product is obtained. Yield: Quantitative STAGE E (Formula Removed) 1.95 g of the product of the previous stage is emulsified in 11.5 ml of a 0.05 N solution of sulphuric acid. The reaction medium is heated at 70°C for 1 hour 3 0 minutes, allowed to return to ambient temperature then neutralized with 0.3 g of barium carbonate. The suspension is agitated for one hour at ambient temperature (pH=7), then filtered and evaporated to dryness. In order to dry it, the product is entrained twice with toluene. After drying (overnight at 40°C in the presence of P2Os) , 1.2 g of sought product is obtained. Yield: Quantitative EXAMPLE 8: 7-[(6-deoxy-6-C-methyl-4-0-methyl-3-0-[[(2- propynyloxy)amino]carbonyl]-.alpha.-L-mannopyranosyl)oxy]-4- hydroxy-8-methyl-3- [1- [ (2-propynyloxy) imino] ethyl] -2H-1- benzopyran-3-yl]-2-one 7-[(6-deoxy-6-C-methyl-4-0-methyl-3-0-[[(2- propynyloxy)amino]carbonyl]-.alpha.-L-mannopyranosyl)oxy]-4- hydroxy-3-[1-(methoxyimino)ethyl]- 8-methyl-2H-1-benzopyran- 2-one STAGE A (Formula Removed) 1.16 g of the product of Preparation 6 is solubilized in 25 ml of methylene chloride. 2.19 g of 7-hydroxy-3[(methoxyimino) methyl]-8-methyl-4-(2-propenyloxy)-2H-1-benzopyran-2-one coumarine and 1.89 g of triphenylphosphine are added at ambient temperature, under argon. The suspension is cooled down to 0°C, then 1.12 ml of DEAD is added dropwise. The suspension is agitated for 1 hour at ambient temperature. A further 1.58 g of triphenylphosphine is added followed by 0.93 ml of DEAD at 0°C. After agitation for 1 hour at ambient temperature, 50 ml of pentane is added in order to precipitate the reduced DEAD. The suspension is filtered, the filtrate is evaporated to dryness and purified by chromatography on silica eluting with the eluant mixture toluene with 3% isopropyl alcohol. 0.870 g of white crystals and 0.850 g of a mixture containing traces of reduced DEAD are obtained. The product is rapidly filtered through 100 g of silica 60 eluting with ether. 0.4 g of sought product is obtained. Total weight: 1.27 g. Yield: 44% (Formula Removed) 1.27 g of the product of the previous stage is solubilized in 10 ml of tetrahydrofuran. 0.85 g of carbonyldiimidazole is added and the reaction medium is heated under reflux for 1 hour, followed by dilution with 50 ml of a heptane l/ethyl acetate 2 mixture. The organic phase is washed with twice 50 ml of a 10% aqueous solution of sodium hydrogen sulphate, dried over magnesium sulphate and evaporated to dryness. 1.41 g of sought product is obtained. Yield: Quantitative STAGE C (Formula Removed) 0.6 g of the product of the previous stage is solubilized in 6.5 ml of pyridine dried over potash. 1.5 g of propargyl-hydroxylamine hydrochloride and 0.149 of lithium perchlorate are added at ambient temperature. Agitation is carried out for 48 hours at ambient temperature. The reaction medium is diluted with a heptane l/ethyl acetate 2 mixture and the organic phase is washed with a 10% solution of sodium hydrogen sulphate, dried over magnesium sulphate. 1.8 g of product is obtained which is chromatographed on silica eluting with a methylene chloride 80/ethyl acetate 19/acetic acid 1 mixture. 186 mg of sought product 3-isomer, 400 mg 2-isomer were obtained. Yield: 74% Opening of the carbonate of which 30% 3-isomer. STAGE D (Formula Removed) 0.4 g of the product of the previous stage (2-isomer) is solubilized in 10 ml of methylene chloride. 100 µl of DBU is added. Agitation is carried out for 24 hours at ambient temperature. The reaction medium is diluted with a heptane l/ethyl acetate 2 mixture and the organic phase is washed with a 1M solution of sodium dihydrogen phosphate, dried over magnesium sulphate and evaporated to dryness. In a 100 ml flask, 0.4 g of the mixture obtained previously is solubilized in 10 ml of ethanol. 0.59 g of methylhydroxy1 amine hydrochloride and 0.76 g of sodium acetate are added at ambient temperature. The reaction medium is agitated for 5 hours at ambient temperature. The reaction medium is diluted with a heptane l/ethyl acetate 2 mixture and the organic phase is washed with a 1M solution of sodium dihydrogen phosphate, dried over magnesium sulphate and evaporated to dryness. 0.45 g of crude product is obtained which is purified on 12 plates of 0.5 mm of silica with the eluant mixture methylene chloride/ethyl acetate 19 / acetic acid 1. Only the expected isomer in 3 is isolated. 0.140 g of sought product is obtained. Yield: 37% Preparation 7 STAGE A (Formula Removed) Under argon, 26.8 g of product is solubilized in 250 ml of tetrahydrofuran. 400 ml of a 1M solution of ethylmagnesium bromide in tetrahydrofuran is added dropwise at 0°C under argon. The solution is agitated for 2 hours at ambient temperature. The reaction medium is cooled down to 0°C and is diluted with 100 ml of heptane. In order to neutralize the excess magnesium, 300 ml of a 1 molar aqueous solution of sodium dihydrogen phosphate is added dropwise. The magnesium salts precipitate. 200 ml of a heptane 1/ethyl acetate 2 mixture and 150 ml of a 10% solution of sodium hydrogen sulphate are added. The organic solution is dried over magnesium sulphate and evaporated to dryness. 29 g of product is obtained which is chromatographed on silica eluting with a Heptane 1/ethyl acetate 4 mixture. 17 g of sought product is obtained. Yield 52%. (Formula Removed) 16.7 g of the product of the previous stage is solubilized under argon in 150 ml of dimethylfomamide. 10.07 g of imidazole is added, then 19.23 ml orf diphenylterbuthylsilyl chloride at 0°C under argon is added dropwise over 3 0 minutes. (Formula Removed) The solution is agitated for 1 hour 3 0 minutes at ambient temperature. The reaction medium is diluted with 400 ml of a heptane l/ethyl acetate 2 mixture. The organic phase is washed with a 1 molar aqueous solution of sodium dihydrogen phosphate, dried over magnesium sulphate and evaporated to dryness. 3 8 g of product is obtained which is purified by chromatography on silica eluting with a methylene chloride mixture with 10% acetone. 33.23 g of sought product is obtained. Yield: Quantitative STAGE C (Formula Removed) 22.57 g of pyridinium chlorochromate 0.104 moles is suspended in 300 ml of methylene chloride. 110 g of 4A molecular sieve is then added. 33 g of the product of the previous stage in solution in 100 ml of methylene chloride is introduced into this suspension. After 3 hours of agitation at ambient temperature, the reaction is finished. The suspension is filtered. The filtrate is evaporated to dryness. The residue obtained (35 g) is purified on silica with the eluant mixture heptane 4/ethyl acetate 1. 27 g of sought product is obtained. Yield 83%. STAGE D (Formula Removed) 16.5 g of the product of the previous stage is solubilized in 150 ml of tetrahydrofuran. 17.52 ml of a 3 molar solution of methylmagnesium bromide in ether is added dropwise under argon, at -5°C. Agitation is carried out for 1 hour at ambient temperature. At 0°C, the excess magnesium is neutralized with a 1M aqueous solution of sodium dihydrogen phosphate. 200 ml of a heptane l/ethyl acetate 2 mixture is added. The organic phase is washed with 200 ml of a 1 molar aqueous solution of sodium dihydrogen phosphate, dried over magnesium sulphate and evaporated to dryness. The product obtained is impasted in pentane. 14.85 g of sought product is obtained. Yield: 87% STAGE E (Formula Removed) 14.85 g of the product of the previous stage is solubilized in 150 ml of tetrahydrofuran. 33 ml of a 1 molar solution of tetrabutylammonium fluoride in tetrahydrofuran is added dropwise under argon, at 0°C. After agitation for 3 0 minutes at ambient temperature, the reaction is terminated. 200 ml of a heptane l/ethyl acetate 2 mixture is added. The organic phase is washed with 200 ml of a 1 molar aqueous solution of sodium dihydrogen phosphate, dried over magnesium sulphate and evaporated to dryness. The crude product is purified on silica eluting with a methylene chloride mixture with 15% acetone then 3 0% acetone. 7.85 g of sought product is obtained. Yield: Quantitative STAGE F (Formula Removed) 7.85 g of the product of the previous stage is solubilized in 82.5 ml of methylene chloride. 44.5 ml of triethylamine and 82.5 ml of dimethylsulphoxide stored on a molecular sieve are added under argon, at ambient temperature. The solution is cooled down to approximately 5°C with an ice-water bath and 15.8 g of pyridine sulphur trioxide is added by fractions without the temperature exceeding 15°C. Agitation is carried out for 1 hour. The reaction medium is poured into 1 litre of a 1 molar aqueous solution of sodium dihydrogen phosphate, the aqueous phase is extracted with a heptane l/ethyl acetate 2 mixture. The organic phase is washed with water, dried over magnesium sulphate and evaporated to dryness. The product obtained is impasted in pentane. 5.77 g of sought product is obtained. Yield 80%. STAGE G (Formula Removed) 5.46 g of the product of the previous stage is solubilized in 25 ml of tetrahydrofuran. 16.7 ml of a 1.5M solution of DIBAL in toluene is added under argon, at 0°C. Agitation is carried out for 1 hour 3 0 minutes at 0°C. The reaction medium is poured into 250 ml of a 1M solution of sodium and potassium double tartrate; the aqueous phase is extracted with a heptane l/ethyl acetate 2 mixture. The organic phase is washed with 150 ml of a 10% aqueous solution of sodium sulphate, dried over magnesium sulphate and evaporated to dryness. 5.5 g of sought product is obtained. Yield: Quantitative STAGE H (Formula Removed) 5.5 g of the product of the previous stage is emulsified in 32 ml of a 0.05N solution of sulphuric acid. After heating at 70°C for one hour 30 minutes, the reaction is terminated. The reaction medium is allowed to return to ambient temperature and neutralized with 0.6 g of barium carbonate; the suspension is agitated for one hour at ambient temperature (pH=7), then filtered on milipore filter paper and evaporated to dryness. In order to dry it, the product is entrained twice with toluene. The reaction medium is dried at 40°C in the presence of P205, 4.8 g of a gummy white residue is obtained. Quantitative yield. EXAMPLE 9 (2-propynyloxy)-carbamic acid 3'-ester of 7- [ (6-deoxy-5-C-ethyl-4-0-methyl-.beta.-D-gulopyranosyl)oxy]-4-hydroxy-8-methyl-3-[1-[(2-propynyloxy)imino]ethyl]-2H-l-benzopyran-2-one (2-propynyloxy)-carbamic acid 3"-ester of 7-[(6-deoxy-5-C-ethyl-4-O-methyl-.beta.-D-gulopyranosyl)oxy]-4-hydroxy-3-[1- (methoxyimino]ethyl]-8-methyl-2H-l-benzopyran-2-one (2-propynyloxy)-carbamic acid 3'-ester of 7-[(6-deoxy-5-C-methyl-4-O-methyl-.beta.-D-gulopyranosyl)oxy]-4-hydroxy-8-methyl-3-[1-[(ethoxy)imino]ethyl]-2H-l-benzopyran-3-yl] -2-one STAGE A (Formula Removed) In a 100 ml flask, 4.8 g of the product of Preparation 7 is solubilized in 100 ml of methylene chloride. 9.98 g of coumarine and 7.23 g of triphenylphosphine are added at ambient temperature, under argon. The suspension is cooled down to 0°C, and 4.3 4 ml of DEAD is added dropwise. The slightly yellow suspension is agitated for 1 hour at ambient temperature. A further 6 g of triphenylphosphine (0.023 mole) is added followed by 3.57 ml of DEAD at 0°C. A yellow solution is obtained. After agitation for 1 hour at ambient temperature, 5 0 ml of pentane is added in order to precipitate the reduced DEAD. The suspension is filtered, the filtrate is evaporated to dryness and purified over 1.750 Kg of silica 60 with the eluant mixture toluene with 3% isopropyl alcohol (the elution is finished with 6%). 10 g of white crystals are obtained containing traces of reduced DEAD. The product is rapidly filtered through 10 0 g of silica 60 with the eluant mixture heptane 1/ethyl acetate 2 in order to eliminate the reduced DEAD, then with a methylene chloride 95/methanol 5 mixture in order to obtain the expected product. 7.3 g of white crystals are obtained. Yield: 58% STAGE B (Formula Removed) 7.1 g of the product of the previous stage is introduced into 100 ml of THF. 4.41 g of diimidazole carbonate is added and the reaction medium is heated under reflux for one hour. The reaction medium is poured into 150 ml of a 10% solution of hydrogen phosphate and extracted with a mixture of hexane ethyl acetate, followed by drying and 7.1 g of sought product is obtained. STAGE C. (Formula Removed) OH 7.1 g of product is solubilized in 100 ml of tetrahydrofuran. 0.7 g of palladium on carbon is added and the reaction medium is placed under a hydrogen atmosphere. After agitation for 3 hours, the reaction is terminated. The reaction medium is filtered and the filtrate is evaporated to dryness. The product is recrystallized from an ether/pentane mixture. 4.75 g of sought product is obtained. Yield: 95% STAGE D (Formula Removed) 1.5 g of product is dissolved in 25 ml of methylene chloride. 0.90 g of dimethylaminopyridine is added then 0.38 ml of acetic anhydride is added dropwise under argon, at 0°C. After agitation for 30 minutes at 0°C, 95µl of acetic anhydride and 0.225 g of dimethylaminopyridine are added. Agitation is carried out for 45 minutes. The reaction medium is diluted with 100 ml of a heptane l/ethyl acetate 2 mixture. The organic phase is washed twice with 150 ml of a IM aqueous solution of sodium dihydrogen phosphate, dried over magnesium sulphate and evaporated to dryness. The expected product is isolated. 1.56 g of sought product is obtained. Yield: 93% STAGE E (Formula Removed) 1.5 g of the product of the previous stage is solubilized in 15 ml of pyridine dried over potash. 3.6 g of propargylhydroxylamine hydrochloride and 0.36 g of lithium perchlorate are added at ambient temperature. The reaction medium is agitated for 48 hours at ambient temperature. The reaction medium is diluted with a heptane l/ethyl acetate 2 mixture and the organic phase is washed with a 10% solution of sodium hydrogen sulphate, and dried over magnesium sulphate. 1.8 g of sought product is obtained. 200 mg of this crude product is purified on silica with the eluant mixture methylene chloride 80/terbutylmethylether 20. The following are obtained: 1st batch: 90 mg of white crystals of sought product. 2nd batch: 75 mg of white crystals: 2-isomer Yield: 77% 55/45 3-isomer STAGE F (Formula Removed) 0.5 g of the product of the previous stage is dissolved in 5 ml of ethanol. 0.85 g of methylhydroxylamine hydrochloride and 0.94 g of potassium acetate are added at ambient temperature. The reaction medium is agitated for 5 hours at ambient temperature, then diluted with a heptane 1/ethyl acetate 2 mixture and the organic phase is washed with a 1M solution of sodium dihydrogen phosphate, dried over magnesium sulphate and evaporated to dryness. A crude product is obtained which is purified on silica with the eluant mixture methylene chloride with 20% terbutylmethylether. 0.103 g of sought product is obtained. STAGE G (Formula Removed) 0,103 g of the sought product isomer in 3 is obtained using 0,85 g of ethylhydroxylamise chloride by operation as in stage F. EXAMPLE 10 STAGE A (Formula Removed) 0.6 g of the product of stage C of example 9 is solubilized in 15 ml of methylene chloride. 0.3 6 g of dimethylaminopyridine is added then 0.209 of propionic anhydride is added dropwise under argon, at 0°C. Agitation is carried out for 30 minutes at 0°C then for 1 hour at ambient temperature and the reaction is terminated. The reaction medium is diluted with 100 ml of a heptane 1/ethyl acetate 2 mixture. The organic phase is washed with a 1M aqueous solution of sodium dihydrogen phosphate, dried over magnesium sulphate and evaporated to dryness. 0.6 g of sought product is obtained. Yield: 68% STAGE B (Formula Removed) 0.6 g of the product of the previous stage is solubilized in 6 ml of pyridine dried over potash. 1.3 9 g of propargylhydroxylamine hydrochloride and 0.13 g of lithium perchlorate are added at ambient temperature. The reaction medium is agitated for 4 8 hours at ambient temperature, then diluted with a heptane 1/ethyl acetate 2 mixture. The organic phase is washed with a 10% sodium hydrogen sulphate solution, then dried over magnesium sulphate. 0.56 g of product is obtained which is solubilized in 10 ml of ethanol, then 1.0 7 g of methylhydroxylamine hydrochloride and 1.3 9 g of sodium acetate are added. The reaction medium is agitated for 5 hours at ambient temperature then diluted with a heptane 1/ethyl acetate 2 mixture. The organic phase is washed with a 1M sodium dihydrogen phosphate solution, dried over magnesium sulphate and evaporated to dryness. 0.45 g of crude product is obtained which is purified by chromatography on silica eluting with a methylene chloride mixture with 20% terbutylmethylether. 0.170 g of sought product is obtained. By operating as previously , the products were also prepared corresponding to the formula: (Formula Removed) By operating as previously the following products were obtained corresponding to formula (I): (Formula Removed) (Table Removed) By operating as previously the following products were prepared: Nomenclature (2-propynyloxy)-carbamic acid 3'-ester of 3-[1-[[(5-chloro-1.2, 3-thiadiazol-4-yl)methoxy]imino]ethyl]-7-[(6-deoxy-5-C-methyl-4-0-methyl-.alpha.-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-2H-l-benzopyran-2-one (2-propynyloxy)-carbamic acid 3'-ester of 3-[l-[(cyanomethoxy)imino]ethyl]-7-[(6-deoxy-5-C-methyl-4-0-methyl-.alpha.-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-2H-1-benzopyran-2-one (2-propynyloxy)-carbamic acid 3'-ester of 3-[l-[(2-aminoethoxy)imino]ethyl]-7-[(6-deoxy-5-C-methyl-4-0-methyl-.alpha.-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-2H-1-benzopyran-2-one (2-propynyloxy)-carbamic acid 3'-ester of 7-[[6-deoxy-5-C-methyl-4-0-methyl-.alpha.-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-3[1-[(2-hydroxyethoxy)imino]ethyl]-2H-1-benzopyran-2 -one (2-propynyloxy)-carbamic acid 3'-ester of 7-[(6-deoxy-5-C-methyl-4-0-methyl-.alpha.-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-3-[1-[[(3-piperidinyl)oxy]imino]ethyl]-2H-1-benzopyran-2-one(isomer B) (2-propynyloxy)-carbamic acid 3'-ester of 7-[(6-deoxy-5-C-methyl-4-0-methyl-.alpha.-L-lyxo-hexopyranosyl)oxy] -4-hydroxy-8-methyl-3-[1-[[(3-piperidinyl)oxy]imino]ethyl]-2H-1-benzopyran-2-one(isomer A) (2-propynyloxy)-carbamic acid 3'-ester of 7-[ (6-deoxy-5-C-methyl-4-0-methyl-.alpha.-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-3-[1-[(1-methylethoxy)imino]ethyl]-2H-1-benzopyran-2-one (2-propynyloxy)-carbamic acid 3'-ester of 3-[l-[(cycobutyloxy)imino]ethyl]-7-[(6-deoxy-5-C-methyl-4-0-methyl-.alpha.-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-2H-1-benzopyran-2-one (2-propynyloxy)-carbamic acid 3'-ester of 7-[(6-deoxy-5-C-methyl-4-0-methyl-.alpha.-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-3-[1-(propoxyimino)ethyl]-2H-1-benzopyran-2-one (2-propynyloxy)-carbamic acid 3'-ester of 7-[ (6-deoxy-5-C-methyl-4-0-methyl-.alpha.-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-3-[1-[2.2,2-trifluoroethoxy)imino]ethyl]-2H-1-benzopyran-2 -one (2-propynyloxy)-carbamic acid 3'-ester of 7-[(6-deoxy-5-C-methyl-4-0-methyl-.alpha.-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-3-[1-[[(pentafluorophenyl)methoxy]imino] ethyl]-2H-l-benzopyran-2-one (2-propynyloxy)-carbamic acid 3'-ester of 7-[(6-deoxy-5-C-methyl-4-0-methyl-.alpha.-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-3-[1-[[3-[4-(3-pyridinyl)-lH-imidazol-1-yl]propoxy]imino]ethyl]-2H-1-benzopyran-2-one (2-propynyloxy)-carbamic acid 3'-ester of 7-[(6-deoxy-5-C-methyl-4-0-methyl-.alpha.-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-3-[1-[[2-(1-piperdinyl)ethoxy]imino]ethyl]-2H-1-benzopyran-2 -one (2-propynyloxy)-carbamic acid 3'-ester of 7-[(6-deoxy-5-C-methyl-4-0-methyl-.alpha.-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-3-[1-[[2-(4-morpholinyl)ethoxy]imino]ethyl] -2H-1-benzopyran-2 -one (2-propynyloxy)-carbamic acid 3'-ester of 7-[(6-deoxy-5-C-methyl-4-O-methyl-.alpha.-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-3-[1-(methoxyimino)propyl]-2H-1-benzopyran-2-one (2-propynyloxy)-carbamic acid 3'-ester of 7-[(6-deoxy-5-C-methyl-4-0-methyl-.alpha.-L-lyxo-hexopyranosyl)oxy]-4- hydroxy-8-methyl-3-[1-[(2.2,2-trifluoroethoxy)imino)propyl]-2H-l-benzopyran-2-one (2-propynyloxy)-carbamic acid 3'-ester of 7-[ (6-deoxy-5-C-methyl-4-0-methyl-.alpha.-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-3-[1-(propoxyimino)propyl]-2H-1-benzopyran-2-one (2-propynyloxy)-carbamic acid 3'-ester of 7-[ (6-deoxy-5-C-methyl-4-0-methyl-.alpha.-L-lyxo-hexopyranosyl)oxy]-3-[1-(ethoxyimino)propyl]-4-hydroxy-8-methyl-2H-1-benzopyran-2 -one 7-[[6-deoxy-5-C-methyl-4-0-methyl-3-0-[[(2-propynyloxy) amino]carbonyl]-.alpha.-L-lyxo-hexopyranosyl)oxy]-3-[1-(ethoxyimino)imino]ethyl]-4-hydroxy-8-methyl-2H-l-benzopyran-2-one 7-[[6-deoxy-5-C-methyl-4-0-methyl-3-0-[[(2-propynyloxy) propynyloxy)amino]carbonyl].alpha.-L-lyxo-hexopyranosyl) oxy] -4-hydroxy-8-methyl-3-[1-[[(2-methyl-4thiazolyl)methoxy]imino]ethyl]-2H-l-benzopyran-2-one (2-propynyloxy)-carbamic acid 3'-ester of 7-[(6-deoxy-5-C-methyl-4-0-methyl-.alpha.-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-3-[1-[[(2-thiazolyl)methoxy]imino]ethyl]-2H-1-benzopyran-2-one (2-propynyloxy)-carbamic acid 3'-ester of 7-[(6-deoxy-5-C-methyl-4-0-methyl-.alpha.-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-3-[1-[[(3-furanyl)methoxy]imino]ethyl]-2H-1-benzopyran-2 -one (2-propynyloxy)-carbamic acid 3'-ester of 7-[(6-deoxy-5-C-methyl-4-O-methyl-.alpha.-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-3-[1-[[(3-thienyl)methoxy]imino]ethyl]-2H-1-benzopyran-2 -one (2-propynyloxy)-carbamic acid 3'-ester of 7-[(6-deoxy-5-C-methyl-4-0-methyl-.alpha.-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-3-[1-[[(2-furanylmethoxy)imino]ethyl]- 8-methyl-2H-1-benzopyran-2-one (2-propynyloxy)-carbamic acid 3'-ester of 7-[(6-deoxy-5-C-methyl-4-0-methyl-.alpha.-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-3-[1-[[(3,5-dimethyl-isoxazol-4-yl)methoxy]imino] ethyl]- 8-methyl-2H-1-benzopyran-2-one (2-propynyloxy)-carbamic acid 3'-ester of 7-[(6-deoxy-5-C-methyl-4-0-methyl-.alpha.-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-3-[1-(phenoxyimino)ethyl]-2H-l-benzopyran-2-one Methyl [[[1-[7-[[6-deoxy-5-C-methyl-4-0-methyl-3-0-[[(2-propynyloxy)amino]carbonyl]-.alpha.-L-lyxo-hexopyranosyl) oxy]-4-hydroxy-8-methyl-2-oxo-2H-l-benzopyran-3-yl]ethyli-dene]amino]oxy]acetate EXAMPLES OF PHARMACEUTICAL COMPOSITIONS Tablets were prepared containing: Product of Example 1 150 mg Excipient s.q.f lg Detail of the excipient: starch, talc, magnesium stearate Product of Example 5 15 0 mg Excipient s.q.f lg Detail of the excipient: starch, talc, magnesium stearate Injectable solutions were also prepared starting from salts. PHARMACOLOGICAL STUDY OF THE PRODUCTS OF THE INVENTION A - Method of dilutions in liquid medium A series of tubes was prepared in which the same quantity of sterile nutritive medium is distributed. Increasing quantities of the product to be studied are distributed in each tube, then each tube is seeded with a bacterial strain. After incubation for 24 hours in an oven at 37°C, the growth inhibition is evaluated by transillumination which allows the minimum inhibitory concentrations (M.I.C.) to be determined expressed in micrograms/cm3. In vitro activity CM1 in µg/ml On the following strains: Ex.1 Ex.2 Ex.3 Ex.4 Staph, aureus 011HT18 0.04 0.04 0.04 0.04 Staph, epidermidis 0126042 0.04 0.04 0.04 0.15 Staph, coag. negative 012HT5 0.3 0.04 0.15 0.15 Strepto. pyogene 02A1UC1 0.6 0.3 0.6 0.6 Strepto. pneumoniae 030BI2 0.04 0.08 0.08 0.15 Entero faecium 02D3IP2 0.08 0.6 1.2 1.2 Entero faecalis 02D2UC5 0.3 1.2 1.2 1.2 B - Inhibition of gyrase B The products are inhibitors of gyrase B; the 50% DNA supercoiling dose is less than 5 µg/ml. WE CLAIM: 1.The aromatic amides compounds of formula (I] (Formula Removed) in which: - Y represents an oxygen atom, or an N-Nalk1 or NOalk3 radical in which alkt and alk2, represent an alkyl radical optionally interrupted by an oxygen, sulphur or nitrogen atom, containing up to 12 carbon atoms optionally substituted by one or more halogen atoms, by an aryl radical optionally substituted by one or more halogen atoms, by one or more radicals (Formula Removed) ,in which Ra and Rb , identical to or different from each other represent a hydrogen atom, an alkyl radical containing up to 8 carbon atoms, optionally substituted, or Ra and Rb being able to form together with the nitrogen atom to which they are joined a heterocycle which can further contain an oxygen or sulphur atom and another nitrogen atom, X represents a hydrogen atom, a hydroxy1 radical, an alkyl, alkenyl or alkynyl radical optionally interrupted by an oxygen, sulphur or nitrogen atom, containing up to 12 linear, branched or cyclic carbon atoms, optionally substituted by one or more halogen atoms, one or more free or esterified OH radicals, C=N, (Formula Removed) in which Ra and Rb, identical or different, represent a hydrogen atom, an alkyl radical containing up to 8 carbon atoms, or Ra and Rb form together with the nitrogen atom to which they are linked a heterocycle optionally containing another heteroatom chosen from nitrogen, sulphur or oxygen, or X represents an alkoxy radical or an (Formula Removed) radical wherein Re is an alkyl radical containing up to 8 carbon atoms, optionally substituted by one or more of the substituents indicated above, or X represents an NReRd radical in which Rc and Rd, identical or different, represent a hydrogen atom or an alkyl radical containing up to 12 carbon atoms, optionally substituted by one or more of the substituents indicated above, or Rc and Rd form together with the nitrogen atom to which they are linked a heterocycle optionally containing another heteroatom chosen from nitrogen, sulphur or oxygen, - Z represents a hydrogen or halogen atom or a free, etherified or esterified OH radical, - R2 represents a hydrogen or halogen atom, - R3 represents a hydrogen atom, an alkyl radical containing up to 8 carbon atoms, or a halogen atom, - R represents a hydrogen atom or an alkyl radical containing up to 4 carbon atoms, - R1 represents a hydrogen atom, an alkyl, alkenyl or alkynyl radical containing up to 8 carbon atoms, linear, branched or cyclic, optionally substituted by one or more halogen atoms, a ON radical, an aryl radical containing up to 14 carbon atoms, R5 represents a hydrogen atom, an O-alkyl radical containing up to 4 carbon atoms, either R6 represents an alkyl, CH2-0-alkyl radical, in which alkyl represents an alkyl radical containing up to 8 carbon atoms, 2-propenyl or ethenyl and R7 represents a hydrogen atom or an alkyl radical containing up to 8 carbon atoms, or R6 and R7 form together with the carbon atom which carries them a ring containing up to 8 carbon atoms as well as the salts of the compound of formula (I), when the compounds of formula (I) have a basic function. 2. The compounds of formula (I) as claimed in claim 1, wherein Y represents an oxygen atom. 3. The compounds of formula (I) as claimed in claim 1, wherein Y represents an NO- alkyl radical in which the alkyl radical contains up to 4 carbon atoms. 4. The compounds of formula (I) as claimed in claim 3, wherein Y represents the NOC2H5 radical. 5. The compounds of formula (I) as claimed in any one of claims 1 to 4, wherein X represents an alkyl radical containing up to 4 carbon atoms and in particular the CH3 radical. 6. The compounds of formula (I) as claimed in any one of claims 1 to 4, wherein X represents an NH2 radical. 7. The compounds of formula (I) as claimed in any one of claims 1 to 4, wherein X represents the radical: (Formula Removed) 8. The compounds of formula (I) as claimed in any one of claims 1 to 7, wherein R1 represents a radical: (Formula Removed) 9. The compounds of formula (I) as as claimed in any one of claims 1 to 8, wherein R represents a hydrogen atom. 10. The compounds of formula (I) as claimed in any one of claims 1 to 9, wherein R3 represents a methyl radical. 11. The compounds of formula (I) as claimed in any one of claims 1 to 10, wherein Z represents a hydrogen atom. 12. The compounds of formula (I) as claimed in any one of claims 1 to 11, wherein R2 represents a hydrogen atom. 13. The compounds of formula (I) as claimed in any one of claims 1 to 12, wherein R5 represents an OCH3 radical. 14. The compounds of formula (I) as claimed in any one of claims 1 to 13, wherein R6 represents a methyl radical. 15. The compounds of formula (I) as claimed in any one of claims 1 to 14, wherein R7 represents a methyl radical. 16. The compounds of formula (I) as claimed in any one of claims 1 to 14, wherein R7 represents an ethyl radical. 17. The compounds of formula (I) as claimed in any one of claims 1 to 13, wherein R6 and R7 form together with the carbon atom which carries them a cyclopentyl radical. 18. The compounds of formula (I) as claimed in claim 1, the names of which follow: - 7-1 [6-deoxy-5-C-methyl-4-O-methyl-3-0- [[(2-propynyloxy) amino] carbony 13 - alpha -L-lyxo-hexopyranosyl]oxy] -4-hydroxy-8-me t hyl - 2 - oxo - 2H-1 -benzopyran- 3 - carboxamide - (2-propynyloxy)-carbamic acid 3'-aster of 7-[(6-deoxy-5-C-methyl-4-0-methyl-alpha-L-lyxo-hexopyranosyl)oxy] -4-hydroxy-8-methyl-N- [2- (4-morpholinyl}ethyl] -2-oxa-2H-4-bensopyran-3-carboxatnide - (E) (2-propynyloxy)-carbamic acid 3 ' -ester of 7-[[6-deoxy-5-c-methyl-4-0-methyl-alpha-L-lyxo-hexopyranosyl] oxy) -4-hydroxy-3- [1- (methoxyimino) ethyl] -8-methyl-2H-l-ben2opyran- 2-one - (2-propynyloxy)-carbamic acid 3'-ester of 7-[ (6-deoxy-5-C-methyl-4-O-methyl-alpha-L-lyxo-hexopyranosyl)oxy] -3- [1-(ethoxyitnino) ethyl] -4 -hydroxy-8-met hyl - 2H- 1-benzopyran-2 - one. 19. The compounds of formula (I) as claimed in claim 1, the names of which follow: (2-propynyloxy)-carbamic 3"-ester acid of 7-[(6-deoxy-5-C-ethyl-4-O-methyl-.beta,-D-gulopyranosyl)oxy}-4-hydroxy-3-[1-(rnethoxyimino)ethyl]-S-methyl-2H-1-be.nzopyran-2-one, 8-hydroxy-7- [4-hydroxy-3- (1- (methoxyimino) ethyl] -3-nnethyl-2-oxo-2H-1-ben20pyran-7-yl] -10-methoxy-6-oxaspiro [4,5] decan-9-yl [7R-(7.alpha.,8.beta,, 9,beta.,10.alpha.)]-(2-propynyloxy)-carbamate 20. A compound of formula (I) as claimed in claim 1, as and when used for preparing a pharmaceutical composition. 21. Preparation process for the compounds of formula (I) as claimed in any one of claims 1 to 19, wherein a compound of formula (II) (Formula Removed) in which the R2, R3, Z, R5, R6 and R7 radicals retain their previous meaning, OW represents a blocked hydroxyl group and W represents an alkyl or Oalkyl radical containing up to 4 carbon atoms, is subjected - to the action of an agent such as herein described capable of introducing the radical vor of a series of operations in a manner such as herein described capable of introducing the radical (Formula Removed) R and R1 retaining their previous meaning, wherein the said introduction of the radical (Formula Removed) is carried out in several stages, first by the action of a phenylchloroformate substituted or not, then the action of a compound of formula (Formula Removed) in which Rl and R retain their previous meaning, - to the action of an agent capable of releasing the hydroxyl radical from the OW radical, - to the optional action of an agent capable of replacing W with radical X which is different from alkyl or oalkyl, - to the optional agent of an agent capable of introducing the Y radical which is different from oxygen, - to the action of a salification agent. 22. A compound of formula (I) substantially as hereinbefore described with reference to the foregoing examples. 23. A process substantially as herein described with reference to the foregoing examples.

Documents:

3839-DEL-1998--Correspondence-Others.pdf

3839-DEL-1998-Abstract (03-06-2008).pdf

3839-DEL-1998-Abstract-(25-06-2008).pdf

3839-del-1998-abstract.pdf

3839-DEL-1998-Claims (03-06-2008).pdf

3839-DEL-1998-Claims-(25-06-2008).pdf

3839-DEL-1998-Claims.pdf

3839-DEL-1998-Correspondence (Others) (03-06-2008).pdf

3839-DEL-1998-Correspondence-Others-(25-06-2008).pdf

3839-del-1998-correspondence-others.pdf

3839-DEL-1998-Description (Complete) (03-06-2008).pdf

3839-del-1998-description (complete)-25-06-2008.pdf

3839-DEL-1998-Description (Complete).pdf

3839-del-1998-form-1.pdf

3839-del-1998-form-18.pdf

3839-DEL-1998-Form-2 (03-06-2008).pdf

3839-del-1998-form-2.pdf

3839-DEL-1998-Form-3 (03-06-2008).pdf

3839-del-1998-form-4.pdf

3839-del-1998-form-6.pdf

3839-DEL-1998-GPA (03-06-2008).pdf

3839-del-1998-gpa.pdf

3839-DEL-1998-Other Document (03-06-2008).pdf

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Claims (03-06-2008).tif

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