HK1131990B - Derivatives of 5-thioxylopyranose and use of same for treatment - Google Patents

Description

The present invention relates to novel compounds of 5-thioxylose, preferably derivatives of the 5-thioxylopyranose type, and their preparation and use as active ingredients in medicinal products, particularly for the treatment or prevention of thrombosis.

Early art

The compounds described in these papers are useful in reducing the risk of venous thrombosis in humans. The mechanism of action of these compounds appears to be an effect on glycosaminoglycans (J. Biol. Chem., Vol 270 no. 6 p 2662-68, Thromb. Haemost. 1999, 81 p 945-950). WO/030785 describes pyropyridinyl 5-thio-β-D-xylopyrranosides as having activity in treating venous thrombosis. EP 365 397 describes β-Denyl-oxyphenyl and their use as antithrombotic and antithrombotic therapeutics.

It is also known that the beneficial effects of a coronary transluminal angioplasty may be compromised by a narrowing of the vessel, causing a further blockage of the arterial light, and therefore compounds to prevent narrowing are of great interest in maintaining a good diagnosis following surgery for atherosclerosis.

New compounds have now been discovered, and this is the subject of the present invention, which are effective when administered orally with an excellent pharmacological result - usually close to 100% - against the occurrence of arterial or venous thrombosis.

Description of the product

Err1:Expecting ',' delimiter: line 1 column 340 (char 339)

The invention also relates to formula I compounds for use as pharmacologically active substances.

In particular, the invention concerns the use of at least one substance selected from the compounds of formula I and their non-toxic salts for the preparation of a medicinal product, useful in human or animal therapy, for the prevention or treatment of thrombosis, in particular venous thrombosis. The compounds of the invention are also useful as active ingredients of medicinal products for the prevention of restenosis after transluminal coronary angioplasty. Since the compounds of the invention are active in a mode of action involving glycosaminoglycans, they may still be useful as active ingredients of a medicinal product for the treatment or prevention of any other disease in which glycosaminoglycans are involved.

Detailed description

In formula I, an alkyl group in C1-C4 is a linear or branched saturated hydrocarbon chain with 1 to 4 carbon atoms or partially or totally cycled, with the cycled portion having 3 or 4 carbon atoms.

Halogen means an atom of fluorine, chlorine, bromine or iodine, preferably a fluorine or chlorine atom.

An acyl group in C2-C6 is an R-CO-group, where R is an alkyl group as defined above with 1 to 5 carbon atoms. Examples of acyl groups in C2-C6 include the acetyl, propanoyl, butanoyl, pentanoyl, hexanoyl groups, and their homologues into which the chain can be branched.

An C1-C4 alcohol group is an RO- group in which R has an alkyl group with 1 to 4 carbon atoms as defined above. Examples of C1-C4 alcohol groups include methoxy, ethoxy, propoxy, butoxy, 1-methylethoxy, 1,1-dimethylethoxy, 1-methylpropoxy, 2-methylpropoxy or cyclopropylmethyoxy.

Addition salts are those obtained by reaction of a compound of formula I with a mineral or organic acid. Preferably, these are pharmaceutically acceptable addition salts. Hydrates or solvates of formula I compounds or salts of formula I compounds are also integral parts of the invention.

Among the mineral acids suitable for salivation of a basic compound of formula I, the preferred are hydrochloric, bromic, phosphoric and sulphuric acids; among the organic acids suitable for salivation of a basic compound of formula I, the preferred are methanesulfonic, benzensulfonic, tolueneulfonic, maleic, fumaric, oxalic, citric, tartaric, lactic and trifluoroacetic acids.

As particular examples of fused bicyclic groups represented by A in the case where R1 and R2 together form an aromatic cycle containing 6 carbon atoms, the groups benzofuranyl, benzothienyl, benzisoxazolyl, benzoxazolyl, benzimidazolyl, quinolinyl, quinoxalinyl, quinazolinyl, indoyl, benzothiazolyl, indazolyl may be mentioned.

Among the compounds of the present invention, those in which the thioxyl group is at position 3 of the pyridine cycle are particularly preferred.

Among the compounds of the present invention, preference is also given to those in which R is the hydrogen atom or the -COCH3 group.

Err1:Expecting ',' delimiter: line 1 column 357 (char 356)

The compounds of formula I of the invention may be prepared by means of glycosylation methods known to the trade, including: (a) the HELFERICH method described in The Carbohydrate, Chemistry and Biochemistry , 2nd edition, Academic Press, New York-London 1972, Volume IA, pages 292-294, by condensation of a peracetyl sugar with an aromatic hydroxy heterocycle in the presence of a Lewis acid;

The compounds of formula I are preferably prepared by methods derived from the processes mentioned above.

Err1:Expecting ',' delimiter: line 1 column 198 (char 197)a trifluoromethyl group; or R1 and R2 together with the atoms of the heterocycle to which they are attached form an aromatic cycle with 6 carbon atoms, A thus representing a fused bicyclic group, in particular a benzofuranyl or benzothienyl group, with a 5-thioxylopyranose derivative of formula: where Hal is a halogen, preferably bromine, and R is an acyl group in C2-C6, preferably the acetyl group, in an aprotic solvent such as acetonitrile or toluene, in the presence of a silver salt, in particular silver oxide or silver imidazolate, or a zinc salt (in particular oxide or chloride) in an anhydrous medium,Err1:Expecting ',' delimiter: line 1 column 188 (char 187)

As an alternative to step (b) described above, the replacement of the acyl group by a hydrogen atom may be carried out by the action of a metal alcohol, preferably sodium methylate in a catalytic quantity, in methanol at a temperature of 0 to 30 °C and for 0,5 to 2 hours to obtain the compound of formula Ia from the compound of formula I in which R represents an acyl group in C2-C6.

Err1:Expecting ',' delimiter: line 1 column 297 (char 296)one hydrogen atom or halogen atom, a cyano group, an alkyl group in C1-C4, an alcohol group in C1-C4, a trifluoromethyl group; orR1 and R2 together with the atoms of the heterocycle to which they are attached form an aromatic cycle comprising 6 carbon atoms, A thus representing a fused bicyclic group, in particular a benzofuranyl or benzothiol group, in an aprotic solvent, such as dichloromethane, in the presence of a Lewis acid-type catalyst, such as tin tetrachloride, at a temperature of 20 to 60 °C for 1 to 2 hours, to obtain the compound with the formula: - What? wherein A,Err1:Expecting ',' delimiter: line 1 column 55 (char 54)

The compound of formula Ib may then be reacted according to the protocol described in the previous process to obtain the unsubstituted pyranosyl compound and/or a salt with an acid.

Err1:Expecting ',' delimiter: line 1 column 295 (char 294)one hydrogen atom or halogen atom, a cyano group, an alkyl group in C1-C4, an alcohol group in C1-C4, a trifluoromethyl group; orR1 and R2 together with the atoms of the heterocycle to which they are attached form an aromatic cycle comprising 6 carbon atoms, A thus representing a fused bicyclic group, in particular a benzofuranyl or benzothiol group, in an aprotic solvent such as dichloromethane, in the presence of a catalyst such as trimethylsilyl trifluoromethane sulfonate, at a temperature of - 25 °C to room temperature and for 1 to 5 hours to obtain thioxylopyranoside of formula: - What? wherein A,Err1:Expecting ',' delimiter: line 1 column 52 (char 51)

The resulting compound of formula Ib may then be reacted as before to obtain the unsubstituted pyranosyl compounds and/or acid salts.

The compounds of formula I of the invention can also be prepared from halogenated derivatives of a glycosylated pyridine, by a Suzuki coupling reaction between two aromatic cycles.

Err1:Expecting ',' delimiter: line 1 column 250 (char 249)a carbon or nitrogen atom,R1, R2 and R3 each independently represent a hydrogen atom or a halogen atom, preferably a fluorine atom, a cyano group, an alkyl group in C1-C4, an alcohol group in C1-C4, a trifluoromethyl group; orR1 and R2 together with the atoms of the heterocycle to which they are attached form an aromatic cycle comprising 6 carbon atoms,Alk represents a hydrogen atom or an alkyl group in C1-C4. in the presence of a palladium catalyst such as [1,1-bisphenylephosphinoferrocene]dichloropalladium dichloromethane, a palladium catalyst immobilized on resin or the Herrmann catalyst, of a polar solvent such as methanol or glycol ether,Err1:Expecting property name enclosed in double quotes: line 1 column 394 (char 393)

Err1:Expecting ',' delimiter: line 1 column 294 (char 293)

Generally, 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide or tetra-O-acetyl-5-thio-α-D-xylopyranose is preferred when a derivative of β-D-5-thio-xylopyranose is to be obtained.

The glycosylation reactions described above most often lead to a mixture of α and β isomers and it is generally necessary to optimise the operating conditions to obtain proportions favourable to the β isomer. For the same reason, it may also be necessary to perform purifications either by recrystallization or chromatography to obtain the pure β isomer.

The following examples are intended to illustrate the invention. The fusion points were measured at the Kofler or capillary bench and the spectral values of nuclear magnetic resonance are characterized by the chemical displacement calculated with respect to the TMS, the number of protons associated with the signal and the shape of the signal (s for singlet, d for double, t for triple, q for quadruplet, m for multiple).

The following abbreviations have been used: mM means millimole (10-3 mole) DMSO means dimethylsulfoxide THF means tetrahydrofuran CHCl3 means chloroform DME means dimethoxyethane

Err1:Expecting ',' delimiter: line 1 column 53 (char 52)

Preparation I: It consists of a mixture of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

The mixture is heated to 90°C and 3,78 g (37,5 mM) of triethylamine and 5,86 g (16,5 mM) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide are added. The product is agitated at 90°C for 20 minutes, then cooled under the reaction, desaturated to clear the minerals that the chlorine washes into the saturated sodium chloride. The organic phosphates are washed into the pH 0.1% solution of sodium chloride and then reduced to a concentrated solution of sodium chloride and sodium amethyl sulfate. F is 128 degrees. - What? ${\left(\alpha \right)}_D^{27}=-92°$ c = 0,23; CHCl3).

Preparation II: The following substances are to be classified in the same heading as the product:

By operating in a similar way to preparation I, starting from 4-bromo-3-pyridinol, the desired product is obtained in the form of a yellow powder (efficiency = 38%). F is 153 degrees. - What? ${\left(\alpha \right)}_D^{30}=-69°$ (c = 0,31; DMSO)

Preparation III: It consists of a mixture of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

By operating in a similar way to preparation I, starting from 2-bromo-3-pyridinol, the desired product is obtained in the form of a white powder (efficiency = 41%). F is 156 degrees. - What? ${\left(\alpha \right)}_D^{24}=-78°$ (c = 0,40; CH3OH)

Preparation IV: The following substances are to be classified in the same heading as the product:

By operating in a similar way to preparation I, starting from 6-bromo-3-pyridinol, the desired product is obtained in the form of a beige powder (efficiency = 43%). F is 145 degrees. - What? ${\left(\alpha \right)}_D^{29}=-20°$ (c = 0,52; DMSO)

Preparation V: It consists of a mixture of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

By operating in a similar way to preparation I, starting from 2-iodo-6-methyl-3-pyridinol, the desired product is obtained in the form of a white powder (efficiency = 81%) F is 187 degrees. - What? ${\left(\alpha \right)}_D^{30}=-88°$ (c = 0,28; DMSO)

Preparation VI: It consists of a mixture of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

By operating in a similar way to preparation I, starting from 2-chloro-4-methyl-3-pyridinol, the desired product is obtained in the form of a white powder (efficiency = 30%). F is 144 degrees. - What? ${\left(\alpha \right)}_D^{30}=+45°$ (c = 0,37; DMSO)

Preparation VII: It consists of a mixture of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

By operating in a similar way to preparation I, starting from 2-bromo-4-pyridinol, the desired product is obtained in the form of a white solid (yield = 37%). F = 162°C (recrystallized in ether). - What? ${\left(\alpha \right)}_D^{29}=-11°$ (c = 0,48; DMSO)

Preparation VIII: The following substances are to be classified in the same heading as the product:

By operating in a similar way to preparation I, starting from 5-bromo-2-fluoro-3-pyridinol, the desired product is obtained in the form of white crystals (efficiency = 39%). F = 120-122°C. (recrystallized in isopropanol)

Preparation IX: The following substances are to be classified in the same heading as the product:

By operating in a similar way to preparation I, starting from 5-bromo-3-pyridinol, the desired product is obtained in the form of a light brown powder (efficiency = 55%). F is 174 degrees. - What? ${\left(\alpha \right)}_D^{20}=-20°$ (c = 0,23; DMSO) is the mean value of the

Preparation X: It consists of a mixture of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

By operating in a similar way to preparation I, starting from 2-chloro-6-iodo-3-pyridinol, the desired product is obtained as a white powder (efficiency = 53%). F = 188°C (recrystallized in ethyl ether). - What? ${\left(\alpha \right)}_D^{30}=-34°$ (c = 0,39; DMSO)

Preparation XI: It consists of a mixture of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

By operating in a similar way to preparation I, starting from 6-chloro-5-fluoro-3-pyridinol, the desired product is obtained in the form of white flakes (efficiency = 43%). F = 158-162°C (recrystallized in ethanol). - What? ${\left(\alpha \right)}_D^{27}=-21°$ (c = 0,33; DMSO) is the mean value of the

Preparation XII: It consists of a mixture of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

By operating in a similar way to preparation I, starting from 2-fluoro-6-iodo-3-pyridinol, the desired product is obtained in the form of a white powder (efficiency = 41%). F = 234°C (recrystallized in ethyl ether). - What? ${\left(\alpha \right)}_D^{30}=-10°$ (c = 0,49; DMSO)

Preparation XIII: It consists of a mixture of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

By operating in a similar way to preparation I, starting from 6-chloro-2-pyridinol, the desired product is obtained as a white powder (yield = 20%). F is 127 degrees. - What? ${\left(\alpha \right)}_D^{29}=-72°$ (c = 0,33; CHCl3) is the concentration of the substance in the solution.

Preparation XIV: The following substances are to be classified in the same heading as the product:

By operating in a similar way to preparation 1, starting from 5-bromo-2-chloro-3-pyridinol, the desired product is obtained in the form of beige crystals (efficiency = 38%). F = 143-147°C. (crystallized in ethyl ether) - What? ${\left(\alpha \right)}_D^{24}=-35°$ (c = 0,15; DMSO)

Preparation XV It consists of a mixture of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

A solution of 1.7 g (14.17 mM) of 2-cyano-3-pyridinol is prepared in 80 ml of acetonitrile and added, in the absence of light, 4.3 g (18.3 mM) of silver oxide and 3 g of molecular sieve 13X. The mixture is stirred for 10 min at 50 °C then 6.5 g (18.3 mM) of 2,3,4-tri-O-acetyl-D-xylopyranoside bromide is added and the reaction mixture is maintained for 18 h under stirring at 50 °C. The mixture is cooled at room temperature and filtered on filtration adjuvant. The yarn is diluted with N-ethyl acetate and washed with water, a solution of N-ethyl bromide until pH is neutral, and then the mixture is removed from the mixture.The residual oil is crystallized by addition of ethyl ether, resulting in 0.89 g of the expected product in the form of beige crystals (yield = 16%). The frequency of the radio spectrum is determined by the frequency bands of the radio spectrum. The product contains a small proportion of α derivatives, whose anomalous proton gives signals at δ = 5.76 and δ = 5.63).

Example 1: The following substances are to be classified in the same category as the active substance:

To a solution of 1 g (2,23 mM) 6-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by IV preparation in 10 ml of DME, add a solution of 0,354 g (3,34 mM) sodium carbonate in 3 ml of water, 0,18 g (0,223 mM) [1,1'-bisphenylephosphino) ferrocene] (dichloropalladium II) dichloromethane and 0,68 g (4,46 mM) 2-methoxy-3-pyridine boronic acid. The mixture is evaporated by microwave solvents at 120°C for 20 minutes, then cooled with water and acetone. The product is washed in a neutral phase with sodium toluene sulphate (Methyl sulphate) and then purified by an organic process to obtain a solution of sodium sulphate, reduced to 70/10 of pH. F is 176 degrees. - What? ${\left(\alpha \right)}_D^{29}=+5°$ The concentration of the active substance in the test chemical is calculated as follows:

Example 2: 6- ((2-methoxy-3-pyridinyl) -3-pyridinyl 5-thio-β-D-xylopyranoside

A 0.3 g (0.63 mM) solution of 6-(2-methoxy-3-pyridinyl)-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained as in example 1 is agitated at room temperature for 4 hours in 4 ml of a 7 M ammonia solution in methanol. The reaction mixture is then concentrated under reduced pressure and the evaporation residue is crystallized in ether. The desired product is obtained as a white solid with an efficiency of 81%. F is 127 degrees. - What? ${\left(\alpha \right)}_D^{29}=-45°$ (c = 0,26; DMSO) is the mean value of the

Example 3: The following substances are to be classified in the same category as the active substance:

By operating in a manner analogous to example 1, the desired product is obtained from 2-chloro-4-methyl-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation VI and 3-pyridineboronic acid in the form of a white foam (yield = 27%) F is 143 degrees. - What? ${\left(\alpha \right)}_D^{33}=+29°$ (c = 0,43; DMSO)

Example 4: The following substances are to be classified in the same category as the active substance:

By operating in a similar way to example 2, the desired product is obtained as white cotton (yield = 40%). F is 98 degrees. - What? ${\left(\alpha \right)}_D^{29}=+66°$ (c = 0,20; DMSO)

Example 5: 2- (3-furanyl) -6-methyl-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 1, the desired product is obtained as a white solid from 2-iodo-6-methyl-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation V and 3-furaneboronic acid (yield = 42%). F is 117 degrees. - What? ${\left(\alpha \right)}_D^{25}=-73°$ (c = 0,10; DMSO)

Example 6: 2- (furanyl) 6-methyl-3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a similar way to example 2, the desired product is obtained as a creamy white solid (yield = 81%) from the product prepared in example 5. F is 162 degrees. - What? ${\left(\alpha \right)}_D^{29}=-117°$ (c = 0,10; DMSO)

Example 7: 2- (methyl-2-furanyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 1, the desired product is obtained as a white solid from 2-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation III and 5-methyl-2-furaneboronic acid (yield = 45%). F is 128 degrees. - What? ${\left(\alpha \right)}_D^{32}=-68°$ (c = 0,27; DMSO)

Example 8: 2- (methyl-2-furanyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a similar way to example 2, the desired product is obtained as a white solid (yield = 83%) from the product prepared in example 7. F is 191 degrees. - What? ${\left(\alpha \right)}_D^{30}=-103°$ (c = 0,28; DMSO)

Example 9: 2-chloro-6-(3-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner similar to example 3, the desired product is obtained as a beige powder from 2-chloro-6-iodo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation X (efficiency = 34%). F is 155 degrees. - What? ${\left(\alpha \right)}_D^{36}=-38°$ (c = 0,13; DMSO) is the mean value of the

Example 10: It consists of a mixture of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

By operating in a similar way to example 2, the desired product is obtained in the form of a beige powder (yield = 35%). F is 180 degrees. - What? ${\left(\alpha \right)}_D^{35}=-51°$ (c = 0,11; DMSO) is the mean value of the

Example 11: 2-fluoro-5-(4-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner similar to example 1, the desired product is obtained from 5-bromo-2-fluoro-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation VIII and 4-pyridineboronic acid in the form of a beige foam (yield = 53%). F = 143 to 144 degrees Celsius. - What? ${\left(\alpha \right)}_D^{30}=+8°$ (c = 0,26; DMSO) is the mean value of the

Example 12: The following substances are to be classified in the same heading as the active substance:

By operating in a similar way to example 2, starting with the product prepared in example 11, the desired product is obtained in the form of pink foam (yield = 59%). F is 98-102°C. - What? ${\left(\alpha \right)}_D^{30}=-61°$ (c = 0,28; DMSO)

Example 13: 2-chloro-6-(2-methoxy-3-pyridinyl)-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside, whether or not in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the solution in the form of a solution in the form of a solution in the solution in the form of a solution in the solution in the form of a solution in the solution in the form of a solution in the solution in the solution in the form of a solution in the solution in the solution in the solution in the form of an solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in

By operating in a manner similar to example 1, the desired product is obtained from 2-chloro-6-iodo-3-pyridinyl 2,3.4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation X and 2-methoxy-3-pyridineboronic acid in the form of a pink solid (yield = 40%). F is 221°C. - What? ${\left(\alpha \right)}_D^{30}=-44°$ (c = 0,20; DMSO)

Example 14: 2-chloro-6-(2-methoxy-3-pyridinyl)-3-pyridinyl 5-thio-β-D-xylopyranoside, whether or not in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the solution in the form of a solution in the form of a solution in the solution in the form of a solution in the solution in the form of a solution in the solution in the solution in the solution in the solution in the form of a solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation

By operating in a similar way to example 2, the desired product is obtained in the form of white cotton (yield = 60%). F = 102°C (recrystallized in a methanol/water mixture). - What? ${\left(\alpha \right)}_D^{30}=-53°$ (c = 0,16; DMSO)

Example 15: It consists predominantly of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

By operating in a manner similar to example 1, the desired product is obtained from 2-chloro-6-iodo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation X and 2-fluoro-3-pyridineboronic acid in the form of a white powder (yield = 27%). F = 227°C (recrystallized in ethanol). - What? ${\left(\alpha \right)}_D^{30}=-38°$ (c = 0,61; DMSO) is the mean value of the

Example 16: It consists of a mixture of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

By operating in a similar way to example 2, the desired product is obtained in the form of white cotton (yield = 80%) from the product prepared in example 15. F = 153°C (recrystallized in an ethanol/water mixture). - What? ${\left(\alpha \right)}_D^{30}=-28°$ (c = 0,48; DMSO)

Example 17: It consists predominantly of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

By operating in a manner similar to example 1, the desired product is obtained from 2-chloro-6-iodo-3-pyridinyl 2.3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation X and 2-fluoro-4-pyridineboronic acid in the form of a white powder (yield = 37%). F = 226°C (recrystallized in a water/acetonitrile mixture). - What? ${\left(\alpha \right)}_D^{32}=-34°$ (c = 0,31; DMSO)

Example 18: It consists of a mixture of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

By operating in a similar way to example 2, the desired product is obtained as a white powder (yield = 27%) from the product prepared in accordance with example 17. F = 195°C (recrystallized in an isopropanol/water mixture). - What? ${\left(\alpha \right)}_D^{32}=-41°$ (c = 0,18; DMSO) is the mean value of the

Example 19: 2-chloro-6-(6-fluoro-3-pyridinyl)-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside, whether or not chemically defined

By operating in a manner similar to example 1, the desired product is obtained from 2-chloro-6-iodo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation X and 6-fluoro-3-pyridineboronic acid as a white powder (yield = 43%). F = 226°C (recrystallized in a water/acetonitrile mixture). - What? ${\left(\alpha \right)}_D^{32}=-23°$ (c = 0,26; DMSO) is the mean value of the

Example 20: It consists predominantly of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

By operating in a similar way to example 2, the desired product is obtained in the form of white needles (yield = 27%) starting from the product prepared in example 19. F = 199°C (recrystallized in an ethanol/water mixture). - What? ${\left(\alpha \right)}_D^{32}=-33°$ (c = 0,33; DMSO) is the mean value of the

Example 21: 2-fluoro-6-(4-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to that in Example 11, the desired product is obtained from 2-fluoro-6-iodo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation XII in the form of white cotton (yield = 47%). F = 164°C (recrystallized in a water/acetonitrile mixture). - What? ${\left(\alpha \right)}_D^{30}=-2°$ (c = 0,14; DMSO)

Example 22: The following substances are to be classified in the same heading as the active substance:

By operating in a manner similar to that in Example 2, the desired product is obtained as a white powder (yield = 34%) from the product prepared in Example 21. F = 196°C (recrystallized in a methanol/water mixture). - What? ${\left(\alpha \right)}_D^{30}=-40°$ (c = 0,38; DMSO)

Example 23: 2-chloro-6-(4-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner similar to that in example 11, the desired product is obtained as a white solid from 2-chloro-6-iodo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation X (yield = 13%). F = 179°C (recrystallized in ethyl ether). - What? ${\left(\alpha \right)}_D^{30}=-31°$ (c = 0,30; DMSO)

Example 24: It consists of a mixture of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

By operating in a similar way to example 2, the desired product is obtained as a yellow powder (efficiency = 47%) from the product prepared in accordance with example 23. F = 186°C (recrystallized in a methanol/water mixture). - What? ${\left(\alpha \right)}_D^{30}=-36°$ (c = 0,17; DMSO)

Example 25: 5-(2-chloro-3-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 1, the desired product is obtained as a white solid from 5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IX and 2-chloro-3-pyridineboronic acid (yield = 21%). F is 162 degrees. - What? ${\left(\alpha \right)}_D^{29}=-16°$ (c = 0,36; DMSO)

Example 26: 5-(2-chloro-3-pyridinyl)-3-pyridinyl 5-thio-β-D-xylopyranoside, whether or not chemically defined

By operating in a manner similar to example 2, the desired product is obtained as a white solid (yield = 79%) from the product prepared in accordance with example 25. F is 215 degrees. - What? ${\left(\alpha \right)}_D^{29}=-47°$ (c = 0,35; DMSO)

Example 27: 5- ((6-Methoxy-3-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 1, the desired product is obtained as a white solid from 5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IX and 6-methoxy-3-pyridineboronic acid (yield = 72%). F is 172 degrees. - What? ${\left(\alpha \right)}_D^{29}=-9°$ (c = 0,24; DMSO)

Example 28: 5- ((6-Methoxy-3-pyridinyl) -3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that in Example 2, the desired product is obtained as a white solid (yield = 57%) from the product prepared in Example 27. F is 189 degrees. - What? ${\left(\alpha \right)}_D^{30}=-47°$ (c = 0,34; DMSO) is the mean value of the

Example 29: 5- ((6-chloro-3-pyridinyl) -3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 1, the desired product is obtained as a white solid from 5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IX and 6-chloro-3-pyridineboronic acid (yield = 33%). F is 194 degrees. - What? ${\left(\alpha \right)}_D^{29}=-17°$ (c = 0,30; DMSO)

Example 30: 5-(6-chloro-3-pyridinyl)-3-pyridinyl 5-thio-β-D-xylopyranoside, whether or not chemically defined

By operating in a manner similar to that in Example 2, the desired product is obtained as a white solid (yield = 72%) from the product prepared in Example 29. F is 211°C. - What? ${\left(\alpha \right)}_D^{30}=-46°$ (c = 0,45; DMSO)

Example 31: 5- ((2-Methoxy-3-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 1, the desired product is obtained from 5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IX and 2-methoxy-3-pyridineboronic acid in the form of a solid tar (efficiency = 63%). F is 167 degrees. - What? ${\left(\alpha \right)}_D^{29}=-13°$ (c = 0,27; DMSO)

Example 32: 5-methyl-2-methyl-3-pyridinyl) -3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that in Example 2, the desired product is obtained as a white solid (yield = 77%). F is 209 degrees. - What? ${\left(\alpha \right)}_D^{29}=-90°$ (c = 0,22; DMSO) is the mean value of the

Example 33: 6- ((methyl-2-furanyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner similar to example 1, 6-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IV and 5-methyl-2-furaneboronic acid are used to obtain the desired product in the form of a solid tar (efficiency = 74%). F is 134 degrees. - What? ${\left(\alpha \right)}_D^{29}=+22°$ (c = 0,23; DMSO) is the mean value of the

Example 34: 6- ((methyl-2-furanyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that in Example 2, the desired product is obtained as a fine starch solid (efficiency = 71%) from the product prepared in Example 33. F is 168 degrees. - What? ${\left(\alpha \right)}_D^{30}=-38°$ (c = 0,30; DMSO)

Example 35: 6- ((Methyl-3-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 1, the desired product is obtained as a white solid from 6-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IV and 6-methyl-3-pyridineboronic acid (yield = 62%). F is 181 degrees. - What? ${\left(\alpha \right)}_D^{29}=+15°$ (c = 0,21; DMSO)

Example 36: 6- ((Methyl-3-pyridinyl) -3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to exemption 2, the desired product is obtained as a white powder (efficiency = 48%) from the product prepared in accordance with example 35. F is 228 degrees. - What? ${\left(\alpha \right)}_D^{29}=-46°$ (c = 0,31; DMSO)

Example 37: 6- ((6-chloro-3-pyridinyl) -3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 1, the desired product is obtained as a white solid from 6-bromo-3-pyridinyl 2.3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IV and 6-chloro-3-pyridineboronic acid (yield = 41%). F is 204°C. - What? ${\left(\alpha \right)}_D^{29}=+5°$ (c = 0,22; DMSO) is the mean value of the

Example 38: The following substances are to be classified in the same category as the active substance:

By operating in a manner similar to example 2, the desired product is obtained as a white solid (yield = 62%) from the product prepared in accordance with example 37. F = 170°C (recrystallized in water). - What? ${\left(\alpha \right)}_D^{30}=-32°$ (c = 0,34; DMSO) is the mean value of the

Example 39: 6- ((2-chloro-3-pyridinyl) -3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 1, 6-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IV and 2-chloro-3-pyridineboronic acid are used to obtain the desired product in the form of a solid tar (efficiency = 43%). F is 180 degrees. - What? ${\left(\alpha \right)}_D^{29}=-8°$ (c = 0,42; DMSO)

Example 40: The following substances are to be classified in the same category as the active substance:

Mix 0,394 g (0,82 mM) of the product obtained in sample 39, 25 ml of methanol and 0,025 ml of an 8% sodium methyl solution in methanol. Stir the mixture for 40 minutes at room temperature, filter and dry the precipitate obtained under reduced pressure to 40°C. The desired product is obtained as a white powder with an efficiency of 93%. F = 203°C - What? ${\left(\alpha \right)}_D^{28}=-51°$ (c = 0,30; DMSO)

Example 41: 5-chloro-6-(4-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

0,633 g (1,45 mM) of 5,6-dichloro-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained from preparation I, 0,214 g (1,74 mM) of 4-pyridineboronic acid, 0,595 g (3,9 mM) of caesium fluoride and 0,118 g (0,145 mM) of [1,1'-bisphenylephosphoferene]dichloropalladium (II) -dichloromethane) are mixed in 6 ml of DME. The mixture is heated to 125/50°C for 90 minutes by microwave. The cool vapour is filtered, mixed with phenylenol and the concentrated organic residues are reduced to a clear phase; the product is then chromatographed in the form of a purified solution of dichloromethane obtained by means of a 20/80/80 vapour pressure purification of silicon. F is 153 degrees. - What? ${\left(\alpha \right)}_D^{27}=-52°$ The test chemical is a chemical compound with a specific chemical structure.

Example 42: The following substances are to be classified in the same heading as the active substance:

Mix 0.315 g (0.656 mM) of the product obtained in Example 41, 20 ml of methanol and 0.02 ml of an 8% sodium methyl solution in methanol. Shake the mixture for 40 minutes at room temperature, filter and dry the precipitate obtained under reduced pressure to 50°C. The desired product is obtained as a beige powder with an efficiency of 82%. F is 226 degrees. - What? ${\left(\alpha \right)}_D^{28}=-49°$ (c = 0,15; DMSO)

Example 43: 5-fluoro-6-(4-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to that in Example 41, the desired product is obtained as a white powder from 6-chloro-5-fluoro-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation XI (yield = 38%). F is 165 degrees. - What? ${\left(\alpha \right)}_D^{29}=-28°$ (c = 0,23; DMSO) is the mean value of the

Example 44: The following substances are to be classified in the same heading as the active substance:

By operating in a manner similar to that of Example 42, the desired product is obtained in the form of a grey powder (yield = 55%) from the product prepared in accordance with Example 43. F is 192 degrees. - What? ${\left(\alpha \right)}_D^{29}=-54°$ (c = 0,12; DMSO) is the mean value of the

Example 45: 6- ((4-pyridinyl)-2-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to that described in Example 41, the desired product is obtained from 6-chloro-2-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation XIII in the form of a cream powder (efficiency = 65%). F is 137 degrees. - What? ${\left(\alpha \right)}_D^{28}=-41°$ (c = 0,32 ; CHCl3) is the concentration of the substance in the solution.

Example 46: 6- ((4-pyridinyl)-2-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 42, the desired product is obtained in the form of a greenish powder (efficiency = 98%) from the product prepared in accordance with Example 45. F is 178 degrees. - What? ${\left(\alpha \right)}_D^{29}=-23°$ (c = 0,28; DMSO)

Example 47: 6- ((3-pyridinyl)-2-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to that described in Example 41, the desired product is obtained from 6-chloro-2-pyridinyl 2.3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation XIII and 3-pyridineboronic acid in the form of a cream powder (yield = 38%). F = 141 °C - What? ${\left(\alpha \right)}_D^{29}=-31°$ (c = 0,26; CHCl3) is the concentration of the substance in the solution.

Example 48: 6- ((3-pyridinyl)-2-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 42, the desired product is obtained in the form of a cream powder (efficiency = 99%) from the product prepared in accordance with Example 47. F is 179 degrees. - What? ${\left(\alpha \right)}_D^{29}=-44°$ (c = 0,22; DMSO) is the mean value of the

Example 49: 5- (fluoro-2-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

A mixture of 2.5 g (5.59 mM) 5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained from formula IX, 9 ml of DME, 0.136 g (0.166 mM) of [1,1'-bisphenylephosphinoferrocene]dichloropalladium II-dichloromethane, 2.12 g (8.34 mM) bispyridine-diboron, and 1.64 mM (16,7 mM) potassium acid is heated in a microwave for 30 minutes at 110°C under inert atmosphere. After cooling, the mixture is filtered in water and further cooled to 0.52 g/m2 (2,5 g/m2) of bicarbonate of methanol, 0.166 g/m2 (2,97-bisphenylephosphinoferrocene. The mixture is washed with water and reduced to a solution of sodium sulphate by means of a dilution of sodium triphosphate and sodium triphosphate of methanol. The mixture is produced by washing and cooling the mixture with water at a temperature of 120°C. The mixture is then reduced to a solution of sodium triphosphenol and sodium triphosphenol. F = 164-166°C. - What? ${\left(\alpha \right)}_D^{22}=-16°$ (c = 0,23; DMSO) is the mean value of the

Example 50: 5- (fluoro-2-pyridinyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 42, the desired product is obtained in the form of white crystals (efficiency = 69%) from the product prepared in accordance with Example 49. F = 166-190°C (recrystallized in water). - What? ${\left(\alpha \right)}_D^{22}=-85°$ (c = 0,59; DMSO)

Example 51: 2-fluoro-5-(3-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner similar to that in example 49, the desired product is obtained as a grey solid from 5-bromo-2-fluoro-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation VIII and 3-bromopyridine (yield = 26%). F = 67 to 68 degrees. - What? ${\left(\alpha \right)}_D^{33}=-8°$ (c = 1.90; DMSO) is the mean of the two

Example 52: The following substances are to be classified in the same heading as the active substance:

By operating in a manner similar to that in Example 2, the desired product is obtained as a white solid (yield = 86%) from the product prepared in Example 51. F = 215-216°C. - What? ${\left(\alpha \right)}_D^{33}=-70°$ (c = 0,62; DMSO)

Example 53: 5- ((Methyl-4-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner similar to that in example 49, the desired product is obtained from 5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IX and 4-chloro-3-methylpyridine in the form of beige crystals (yield = 15%). F = 153-174°C (recrystallized in ether). - What? ${\left(\alpha \right)}_D^{23}=-21°$ (c = 0,17; DMSO)

Example 54: 5- ((Methyl-4-pyridinyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 42, the desired product in the form of beige cotton is obtained (yield = 50%) from the product prepared in accordance with Example 53. F = 194 to 214 degrees Celsius. - What? ${\left(\alpha \right)}_D^{23}=-58°$ (c = 0,20; DMSO)

Example 55: 5- ((3-methyl-2-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a similar way to example 53, starting from 2-bromo-3-methylpyridine, the desired product is obtained as a white solid (yield = 17%). F = 148-150°C (recrystallized in ether). - What? ${\left(\alpha \right)}_D^{32}=-22°$ (c = 0,25; DMSO)

Example 56: 5- ((3-methyl-2-pyridinyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 42, the desired product is obtained in the form of a beige solid (yield = 67%) from the product prepared in accordance with Example 55. F = 162-175 degrees. - What? ${\left(\alpha \right)}_D^{32}=-44°$ (c = 0,32; DMSO) is the mean value of the

Example 57: 5-(2,4-dimethyl-5-thiazolyl)-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 53, starting from 5-bromo-2,4-dimethylthiazole, the desired product is obtained which is directly involved in the deacetylation step.

Example 58: 5-2,4-dimethyl-5-thiazolyl)-3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 42, the desired product is obtained as a white solid (yield = 32%) from the product prepared in accordance with Example 57. F is 150 degrees. - What? ${\left(\alpha \right)}_D^{30}=-61°$ (c = 0,10; DMSO)

Example 59: The following substances are to be classified in the same category as the active substance:

By operating in a manner analogous to example 53, starting from 4-bromo-1-methyl-3- ((trifluoromethyl) -H-pyrazole, the desired product is obtained which is directly involved in the deacetylation step.

Example 60: The following substances are to be classified in the same category as the active substance:

By operating in a manner similar to that of Example 2, the desired product is obtained as a white solid (yield = 26%) from the product prepared in accordance with Example 59. F = 210°C. - What? ${\left(\alpha \right)}_D^{29}=-60°$ (c = 0,24; DMSO)

Example 61: The following substances are to be classified in the same category as the active substance:

By operating in a manner analogous to example 53, starting from 4-bromo-5-methyl-3- ((trifluoromethyl) -H-pyrazole, the desired product is obtained which is directly involved in the deacetylation step.

Example 62: The following substances are to be classified in the same category as the active substance:

By operating in a manner similar to example 2, the desired product is obtained in the form of a beige solid (yield = 6%) starting from the product prepared in accordance with example 61. F is 234 degrees. - What? ${\left(\alpha \right)}_D^{29}=-76°$ (c = 0,21; DMSO)

Example 63: 5- ((methyl-4-isoxazolyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a similar way to example 53, starting from 4-iodo-5-methylisoxazole, the desired product is obtained as a white solid (yield = 28%) F is 127 degrees. - What? ${\left(\alpha \right)}_D^{28}=-28°$ (c = 0,22; DMSO) is the mean value of the

Example 64: 5- ((methyl-4-isoxazolyl) -3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 2, the desired product is obtained as a white solid (yield = 79%) from the product prepared in accordance with Example 63. F is 209 degrees. - What? ${\left(\alpha \right)}_D^{28}=-87°$ (c = 0,19; DMSO)

Example 65:

The following substances are to be classified in the same heading as the active substance:

By operating in a similar way to example 53, starting with iodopyrazine, the desired product is obtained as a white powder (yield = 13%) at F = 145°C. - What? ${\left(\alpha \right)}_D^{29}=-11°$ (c = 0,22; DMSO) is the mean value of the

Example 66: The following substances are to be classified in the same heading as the active substance:

By operating in a manner similar to that in Example 2, the desired product is obtained as a white solid (yield = 70%) from the product prepared in Example 65. F is 197 degrees. - What? ${\left(\alpha \right)}_D^{29}=-68°$ (c = 0,20; DMSO)

Example 67: 5- ((2-pyrimidinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a similar way to example 53, starting from 2-bromopyrimidine, the desired product is obtained which is directly involved in the deacetylation step.

Example 68: 5- ((2-pyrimidinyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that in Example 2, the desired product is obtained as a white powder (yield = 31%) from the product prepared in accordance with Example 67. F = 201 °C. - What? ${\left(\alpha \right)}_D^{29}=-69°$ (c = 0,23; DMSO) is the mean value of the

Example 69: 5- (thio-β-D-xylopyranoside) 2-thiazolyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 53, starting from 2-bromothiazole, the desired product is obtained which is directly involved in the deacetylation step.

Example 70: 5- (thio-D-xylopyranoside) 2-thiazolyl-3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that in Example 2, the desired product is obtained as a white powder (yield = 26%) from the product prepared in Example 69. F is 204°C. - What? ${\left(\alpha \right)}_D^{29}=-93°$ (c = 0,20; DMSO)

Example 71: The following substances are to be classified in the same category as the active substance:

By operating in a manner analogous to example 53, starting from 5-bromo-1-methyl-1H-imidazole, the desired product is obtained which is directly involved in the deacetylation step.

Example 72 The following substances are to be classified in the same category as the active substance:

By operating in a manner similar to example 2, the desired product is obtained in the form of a beige powder (yield = 25%). F is 213 degrees. - What? ${\left(\alpha \right)}_D^{29}=-83°$ (c = 0,32; DMSO) is the mean value of the

Example 73: 5-(2-chloro-4-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 1, the desired product is obtained from 5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IX and 2-chloro-4-pyridineboronic acid in the form of a solid tar (efficiency = 55%). F = 105 to 108°C. - What? ${\left(\alpha \right)}_D^{30}=-21°$ (c = 0,30; DMSO)

Example 74: 5-(2-chloro-4-pyridinyl)-3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 42, the desired product is obtained as a white solid (yield = 68%) from the product prepared in accordance with Example 73. F is 204°C. - What? ${\left(\alpha \right)}_D^{30}=-76°$ (c = 0,34; DMSO) is the mean value of the

Example 75: 5- (3-chloro-4-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 73, starting from 3-chloro-4-pyridineboronic acid, the desired product is obtained as a white solid (yield = 39%). F is 175 degrees. - What? ${\left(\alpha \right)}_D^{25}=-22°$ (c = 0,25; DMSO)

Example 76: 5- (3-chloro-4-pyridinyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner analogous to that of Example 42, the desired product is obtained in the form of a white solid (yield = 88%) from the product prepared in accordance with Example 75. F is 208 degrees. - What? ${\left(\alpha \right)}_D^{25}=-72°$ (c = 0,24; DMSO)

Example 77: 6- ((Methoxy-3-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 1, 6-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IV and 6-methoxy-3-pyridineboronic acid are used to obtain the desired product as a white solid (yield = 65%). F is 74 degrees. - What? ${\left(\alpha \right)}_D^{29}=+10°$ (c = 0,44; DMSO)

Example 78: 6- ((6-Methoxy-3-pyridinyl) -3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner analogous to that of Example 42, the desired product is obtained as a white solid (yield = 30%). F is 167 degrees. - What? ${\left(\alpha \right)}_D^{28}=-27°$ (c = 0,23; DMSO) is the mean value of the

Example 79: 2-3-furanyl) -4-methyl-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 1, the desired product is obtained from 2-chloro-4-methyl-3-pyridinyl 2,3,4-tlri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation VI and 3-furaneboronic acid in the form of a solid tar (efficiency = 77%) F is 164 degrees. - What? ${\left(\alpha \right)}_D^{33}=+61°$ (c = 0,23; DMSO) is the mean value of the

Example 80: 2- (furanyl) 4-methyl-3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 42, the desired product is obtained in the form of white cotton (yield = 59%) from the product prepared in accordance with Example 79. F is 95 degrees. - What? ${\left(\alpha \right)}_D^{29}=+83°$ (c = 0,18; DMSO) is the mean value of the

Example 81: 2-(3,5-dimethyl-4-isoxazolyl) -4-methyl-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 79, starting from 3,5-dimethyl-4-isoxazoleboronic acid, the desired product is obtained which is directly involved in the deacetylation step.

Example 82: 2-(3,5-dimethyl-4-isoxazolyl) -4-methyl-3-pyridinyl 5-thio-β-D-xyiopyranoside

By operating in a manner analogous to that of Example 42, starting from the product prepared in accordance with Example 81, the desired product is obtained as a white powder (yield = 20%). F = 70 to 100 degrees. - What? ${\left(\alpha \right)}_D^{25}=+115°$ (c = 0,10; DMSO)

Example 83: 4- ((3-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 1, the desired product is obtained from 4-bromo-3-pyridinyl 2,3,4-ta-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation II and 3-pyridineboronic acid in the form of a solid tar (yield = 57%). F is 159 degrees. - What? ${\left(\alpha \right)}_D^{32}=-72°$ (c = 0,25; DMSO)

Example 84: 4- ((3-pyridinyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner analogous to that of Example 42, the desired product is obtained in the form of a white solid (yield = 86%) from the product prepared in accordance with Example 83. F is 212 degrees. - What? ${\left(\alpha \right)}_D^{30}=-53°$ (c = 0,35; DMSO)

Example 85: 2-(2-benzofuranyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner similar to example 1, 2-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation III and 2-benzofuraneboronic acid are obtained to produce the desired product which is directly involved in the deacetylation step.

Example 86: 2-(2-benzofuranyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner analogous to that of Example 42, the desired product is obtained as a white solid (yield = 15%) from the product prepared in accordance with Example 85. F is 215 degrees. - What? ${\left(\alpha \right)}_D^{32}=-68°$ (c = 0,26; DMSO) is the mean value of the

Example 87: 4-furanyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 83, starting with 3-furaneboronic acid, the desired product is obtained in the form of a solid starch (yield = 36%). F is 167 degrees. - What? ${\left(\alpha \right)}_D^{31}=-77°$ (c = 0,37; DMSO)

Example 88: 4-furanyl-3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner analogous to that of Example 42, the desired product is obtained as a white solid (yield = 64%) from the product prepared in accordance with Example 87. F is 231 degrees. - What? ${\left(\alpha \right)}_D^{32}=-112°$ (c = 0,28; DMSO)

Example 89: 4- ((pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a similar way to example 83, starting with 4-pyridineboronic acid, the desired product is obtained in the form of a solid starch (yield = 55%). F is 185 degrees. - What? ${\left(\alpha \right)}_D^{31}=-114°$ (c = 0,47; DMSO)

Example 90: 4- ((pyridinyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner analogous to that of Example 42, the desired product is obtained as a white solid (yield = 84%) from the product prepared in accordance with Example 89. F is 212 degrees. - What? ${\left(\alpha \right)}_D^{32}=-54°$ (c = 0,26; DMSO) is the mean value of the

Example 91: 5- (β-benzothienyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 73, starting with 2-benzothiopheneboric acid, the desired product is obtained in the form of a beige solid (yield = 72%). F is 168 degrees. - What? ${\left(\alpha \right)}_D^{30}=+7°$ (c = 0,36; DMSO)

Example 92: 5- (β-benzothienyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 42, the desired product in the form of solid starch is obtained from the product prepared in accordance with Example 91 (efficiency = 91%). F is 235°C. - What? ${\left(\alpha \right)}_D^{32}=-50°$ (c = 0,32; DMSO) is the mean value of the

Example 93: 2- (thio-β-D-xylopyranoside) 2- (thio-thyenyle) 3-pyridinyle 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a similar way to example 85, starting with 2-thiophene boronic acid, the desired product is obtained in the form of a solid starch (yield = 51 %). F is 166 degrees. - What? ${\left(\alpha \right)}_D^{32}=-112°$ (c = 0,20; DMSO)

Example 94: 2- (t) 2-thienyl-3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 42, the desired product is obtained in the form of solid starch (efficiency = 80%). F is 130 degrees. - What? ${\left(\alpha \right)}_D^{30}=-90°$ (c = 0,46; DMSO)

Example 95: 5- ((methyl-2-furanyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner similar to example 73, starting with 5-methyl-2-furaneboronic acid, the desired product is obtained in the form of a beige solid (yield = 56%). F is 124 degrees. - What? ${\left(\alpha \right)}_D^{30}=+1°$ (c = 0,40; DMSO)

Example 96: 5- ((methyl-2-furanyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner analogous to that of Example 42, the desired product is obtained as a white solid (yield = 55%) from the product prepared in accordance with Example 95. F is 188 degrees. - What? ${\left(\alpha \right)}_D^{30}=-75°$ (c = 0,40; DMSO)

Example 97: 6- ((2-benzofuranyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 1, 6-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IV and 2-benzofuraneboronic acid are used to obtain the desired product in the form of a solid tar (yield = 65%). F is 179 degrees. - What? ${\left(\alpha \right)}_D^{30}=+13°$ (c = 0,31; DMSO)

Example 98: 6-(2-benzofuranyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner analogous to that of Example 42, the desired product is obtained as a white solid (yield = 50%) from the product prepared in accordance with Example 97. F = 195 degrees. - What? ${\left(\alpha \right)}_D^{30}=-24°$ (c = 0,28; DMSO)

Example 99: 6- (3-thenyl) -3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 97, starting with 3-thiophene boronic acid, the desired product is obtained in the form of a white foam (yield = 66%). F is 158 degrees. - What? ${\left(\alpha \right)}_D^{35}=-9°$ (c = 0,30; DMSO)

Example 100: 6- (3-thenyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 42, the desired product is obtained as a broken white solid (yield = 98%) from the product prepared in accordance with Example 99. F is 154 degrees. - What? ${\left(\alpha \right)}_D^{30}=-50°$ (c = 0,28; DMSO)

Example 101: 2-furanyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a similar way to example 85, starting with 2-furaneboronic acid, the desired product is obtained in the form of a solid starch (yield = 46%). F is 160 degrees. - What? ${\left(\alpha \right)}_D^{28}=-60°$ (c = 0,51; DMSO)

Example 102: 2-furanyl-3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 42, the desired product in the form of solid starch is obtained from the product prepared in accordance with Example 101 (efficiency = 91%). F is 184 degrees. - What? ${\left(\alpha \right)}_D^{34}=-108°$ (c = 0,30; DMSO)

Example 103 6- ((2-furanyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 97, starting with 2-furaneboronic acid, the desired product is obtained as a broken white solid (yield = 64%). F is 133 degrees. - What? ${\left(\alpha \right)}_D^{30}=+16°$ (c = 0,30; DMSO)

Example 104: 6-2-furanyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 42, the desired product is obtained in the form of a pale pink solid (yield = 92%) from the product prepared in accordance with Example 103. F is 146 degrees. - What? ${\left(\alpha \right)}_D^{30}=-53°$ (c = 0,30; DMSO)

Example 105: 2- (pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a similar way to example 85, starting with 4-pyridineboronic acid, the desired product is obtained in the form of a solid starch (yield = 28%) F is 161 degrees. - What? ${\left(\alpha \right)}_D^{28}=-82°$ (c = 0,30; DMSO)

Example 106: 2-4-Pyridinyl) 3-Pyridinyl 5-Thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 42, the desired beige solid product is obtained from the product prepared in accordance with Example 105 (yield = 97%) F is 129 degrees. - What? ${\left(\alpha \right)}_D^{30}=-56°$ (c = 0,40; DMSO)

Example 107: 6- (thio-β-D-xylopyranoside) 2-thyenyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 97, starting with 2-thiophene boronic acid, the desired product is obtained in the form of a solid starch (efficiency = 68%). F is 172 degrees. - What? ${\left(\alpha \right)}_D^{33}=-6°$ (c = 0,40; DMSO)

Example 108: 6- (t) 2-thienyl-3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 42, the desired product is obtained in the form of a beige solid (efficiency = 80%). F is 134 degrees. - What? ${\left(\alpha \right)}_D^{30}=-40°$ (c = 0,38; DMSO)

Example 109: 5-Furanyl-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner similar to example 73, starting with 2-furaneboronic acid, the desired product is obtained in the form of a beige foam (yield = 61%). F is 184 degrees. - What? ${\left(\alpha \right)}_D^{25}=-10°$ (c = 0,28; DMSO)

Example 110: 5-2-furanyl) -3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 42, the desired beige solid product is obtained from the product prepared in accordance with Example 109 (efficiency = 66%). F is 215 degrees. - What? ${\left(\alpha \right)}_D^{30}=-68°$ (c = 0,25; DMSO)

Example 111: 2- (Pyridinyl) 3-Pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 85, starting with 3-pyridineboronic acid, the desired product is obtained in the form of a solid ochre (yield = 28%). F is 70 degrees. - What? ${\left(\alpha \right)}_D^{24}=-70°$ (c = 0,35; DMSO)

Example 112: 2- (Pyridinyl) 3-Pyridinyl 5-Thio-β-D-Xylopyranoside

By operating in a manner analogous to that of Example 42, the desired product in the form of a solid ochre is obtained from the product prepared in accordance with Example 111 (efficiency = 89%). F is 80 degrees. - What? ${\left(\alpha \right)}_D^{30}=-40°$ (c = 0,44; DMSO)

Example 113: 2-furanyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 85, starting with 3-furaneboronic acid, the desired product is obtained as a white solid (yield = 20%). F is 185 degrees. - What? ${\left(\alpha \right)}_D^{25}=-99°$ (c = 0,28; DMSO)

Example 114: 2-furanyl-3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 42, the desired product is obtained as a white solid (yield = 91%) from the product prepared in accordance with Example 113. F is 128 degrees. - What? ${\left(\alpha \right)}_D^{24}=-74°$ (c = 0,30; DMSO)

Example 115: 5-(2-benzofuranyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner similar to example 73, starting with 2-benzofurane boronic acid, the desired product is obtained in the form of a solid starch (yield = 70%). F is 125 degrees. - What? ${\left(\alpha \right)}_D^{29}=+8°$ (c = 0,40; DMSO)

Example 116: 5-(2-benzofuranyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 42, the desired product is obtained as a white solid (yield = 86%) from the product prepared in accordance with Example 115. F = 210°C. - What? ${\left(\alpha \right)}_D^{24}=-44°$ (c = 0,30; DMSO)

Example 117: 6-furanyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 97, starting with 3-furaneboronic acid, the desired product is obtained in the form of a solid starch (efficiency = 66%). F is 187 degrees. - What? ${\left(\alpha \right)}_D^{29}=+3°$ (c = 0,25; DMSO)

Example 118: 6-furanyl-3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 42, the desired product is obtained in the form of solid starch (efficiency = 85%) from the product prepared in accordance with Example 117. F is 132 degrees. - What? ${\left(\alpha \right)}_D^{29}=-29°$ (c = 0,27; DMSO)

Example 119: 6- ((3-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 97, starting with 3-pyridineboronic acid, the desired product is obtained in the form of a solid starch (yield = 50%). F = 196 degrees. - What? ${\left(\alpha \right)}_D^{26}=+4°$ (c = 0,27; DMSO)

Example 120: 6- ((3-pyridinyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 42, the desired product is obtained in the form of a pale pink solid (yield = 99%) from the product prepared in accordance with Example 119. F is 152 degrees. - What? ${\left(\alpha \right)}_D^{28}=-40°$ (c = 0,30; DMSO)

Example 121: 6- ((4-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a similar way to example 97, starting with 4-pyridineboronic acid, the desired product is obtained as a broken white solid (yield = 31%). F is 189 degrees. - What? ${\left(\alpha \right)}_D^{29}=+4°$ (c = 0,40; DMSO)

Example 122: 6- ((4-pyridinyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner analogous to that in Example 42, the desired product in the form of solid starch was obtained from the product prepared in Example 121 (efficiency = 82%) F is 248°C. - What? ${\left(\alpha \right)}_D^{26}=-35°$ (c = 0,34; DMSO) is the mean value of the

Example 123: 5-4-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner similar to example 73, starting with 4-pyridineboronic acid, the desired product is obtained as a broken white solid (yield = 40%). F is 138 degrees. - What? ${\left(\alpha \right)}_D^{27}=-14°$ (c = 0,35; DMSO)

Example 124: 5-4-Pyridinyl) 3-Pyridinyl 5-Thio-β-D-xylopyranoside

0.41 g (0.92 mM) of the product obtained from example 123 is added to a mixture of 6 ml of THF and 6 ml of water. The medium is cooled with an ice bath, 0.385 g (9.18 mM) of lithium hydroxide (monohydrate) is added and stirred for 90 minutes. The reaction medium is partially concentrated under reduced pressure and the resulting aqueous phase is brought to pH 5-6 with a solution of 1N hydrochloric acid. The precipitate product is filtered and dried. The desired product is obtained as a white solid with an 88% yield. F is 213 degrees. - What? ${\left(\alpha \right)}_D^{27}=-48°$ (c = 0,40; DMSO)

Example 125: 5-furanyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 73, starting with 3-furaneboronic acid, the desired product is obtained in the form of a beige solid (yield = 32%) F is 127 degrees. - What? ${\left(\alpha \right)}_D^{27}=-20°$ (c = 0,29; DMSO)

Example 126: 5-Furanyl-3-Pyridinyl 5-Thio-β-D-Xylopyranoside

By operating in a manner similar to that of Example 42, the desired product is obtained in the form of solid starch (efficiency = 93%) from the product prepared in accordance with Example 125. F is 170 degrees. - What? ${\left(\alpha \right)}_D^{27}=-72°$ (c = 0,31; DMSO)

Example 127: 5-Pyridinyl) 3-Pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 73, starting with 3-pyridineboronic acid, the desired product is obtained in the form of a solid starch (yield = 63%). F is 149 degrees. - What? ${\left(\alpha \right)}_D^{23}=-23°$ (c = 0,25; DMSO)

Example 128: 5-Pyridinyl-3-Pyridinyl 5-Thio-β-D-Xylopyranoside

By operating in a manner similar to that of Example 42, the desired product is obtained in the form of solid starch (yield = 50%) from the product prepared in accordance with Example 127. F is 203 degrees. - What? ${\left(\alpha \right)}_D^{23}=-80°$ (c = 0,43; DMSO)

Example 129: 2- (pyridinyl) 4-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner similar to example 1, the desired product is obtained as a white solid from 2-bromo-4-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation VII and 4-pyridineboronic acid (yield = 53%). F is 185 degrees. - What? ${\left(\alpha \right)}_D^{29}=-27°$ (c = 0,13; DMSO) is the mean value of the

Example 130: 2- ((4-pyridinyl) -4-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to example 2, the desired product is obtained as a white solid (yield = 42%) from the product prepared in accordance with example 129. F is 170 degrees. - What? ${\left(\alpha \right)}_D^{29}=-49°$ (c = 0,10; DMSO)

Example 131: 2- ((6-fluoro-3-pyridinyl) -4-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 129, starting from 6-fluoro-3-pyridineboronic acid, the desired product is obtained as a white solid (yield = 51 %). F is 151 degrees. - What? ${\left(\alpha \right)}_D^{29}=-34°$ (c = 0,15; DMSO)

Example 132: 2- ((6-fluoro-3-pyridinyl) -4-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to example 2, the desired product is obtained as a white solid (yield = 94%) from the product prepared in accordance with example 131. F is 171 degrees. - What? ${\left(\alpha \right)}_D^{29}=-66°$ (c = 0,26; DMSO) is the mean value of the

Example 133: 2- (Pyridinyl) 4-Pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 129, starting with 3-pyridineboronic acid, the desired product is obtained in the form of beige crystals (yield = 22 %). F = 185°C (recrystallized in isopropanol). - What? ${\left(\alpha \right)}_D^{31}=-21°$ (c = 0,24; DMSO)

Example 134: 2- (Pyridinyl) 4-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a similar way to Example 2, starting with the product prepared according to Example 133, the desired product is obtained in the form of white crystals (efficiency = 66%). F = 197°C (recrystallized in water). - What? ${\left(\alpha \right)}_D^{29}=-83°\mathrm{.}$ (c = 0,10; DMSO)

Example 135: 5- (2-thienyl) -3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 73, starting with 2-thiophene boronic acid, the desired product is obtained in the form of a solid starch (yield = 57%). F is 166 degrees. - What? ${\left(\alpha \right)}_D^{27}=+6°$ (c = 0,25; DMSO)

Example 136: 5- (thio-β-D-xylopyranoside) 2-thenyl) 3-pyridinyl

By operating in a manner similar to that of Example 42, the desired product is obtained in the form of solid starch (efficiency = 78%) from the product prepared in accordance with Example 135. F = 205 degrees. - What? ${\left(\alpha \right)}_D^{30}=-68°$ (c = 0,40; DMSO)

Example 137: 5- ((Methoxy-3-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

A mixture of 1 g (5.32 mM) 3-bromo-5-methoxypyridine, 10 ml of DME, 2.02 g (7.98 mM) bispinacolato (diborane), 0.13 g (0.16 mM) [1,1'-bisphenylephosphino) ferrocene]dichloropalladium (II) dichloromethane] and 1.5 g (15.96 mM) potassium acetate is heated in a microwave at 110 °C for 30 minutes under argon atmosphere. The mixture is cooled, heated and 1,5 g (3.55 mM) 5-bromo-5-methoxypyridine, 2.4-O-dichlorophenol-dichlorophenol-dichlorophenol-dichlorophenol-dichlorophenol-dichlorophenol is added to the water filtration solution in the presence of water; the product is then prepared in the presence of sodium chlorophenol (II) and sodium chlorophenol (II) for 90 minutes. The product is then reduced to a solid by adding 0,5 g (3.55 mM) sodium chlorophenol-dichlorophenol-dichlorophenol (II) and sodium chlorophenol-dichlorophenol-dichlorophenol (II) to a solution of sodium chlorophenol and sodium chlorophenol-dichlorophenol (II) and a solution of sodium chlorophenol-dichlorophenol-dichlorophenol (II) obtained by adding sodium chlorophenol and sulphate (II) to a solution of sodium chlorophenol and sodium chlorophenol (II) and sodium chlorophenol (II) is then reduced to a solution of sodium chlorophenol (II) and chlorophenol (II) by adding to a solution of sodium chlorophenol and chlorophenol (II) of sodium chlorophenol and sulphor (II) chlorophenol (II) and sulphor (II) chlorophenol (II) to a solution of sodium chlorophenol and a solution of sodium chlorophen F is 181 degrees. - What? ${\left(\alpha \right)}_D^{28}=-7°$ (c = 0,26; DMSO) is the mean value of the

Example 138: 5- ((Methoxy-3-pyridinyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 42, the desired product is obtained as a white solid (yield = 33%) from the product prepared in accordance with Example 137. F is 193 degrees. - What? ${\left(\alpha \right)}_D^{27}=-71°$ (c = 0,40; DMSO)

Example 139: The following substances are to be classified in the same category as the active substance:

The reaction mixture is agitated at room temperature for 5 minutes and 0.192 g (1,5 mM) of bispinacolato) diborabane is added. The reaction mixture is then agitated for 1 hour at room temperature with addition of 4 ml of a saturated sodium bicarbonate solution and extracted in the Oxycodone acetate solid phase. This organic solution is prepared in white water, in the form of sodium pinaxide and sodium sulphate. The reaction is obtained by reducing 5-Oxycodone acetate (Oxycodone 5-Oxycodone) (Hydroxy-Oxycodone) (Hydroxy-Oxycodone) (Hydroxy-Oxycodone) (Hydroxy-Oxycodone) (Hydroxy-Oxycodone) (Hydroxy-Oxycodone) (Hydroxy-Oxycodone) (Hydroxy-Oxycodone) (Hydroxy-Oxycodone) (Hydroxy-Oxycodone) (Hydroxy-Oxycodone) (Hydroxycodone) (Hydroxycodone)) (Hydroxycodone) (Hydroxycodone) (Hydroxycodone) (Hydroxycodone) (Hydroxycodone) (Hydroxycodone) (Hydroxycodone) (Hydroxycodone) (Hydroxycodone) (Hydroxycodone) (Hydroxycodone) (Hydroxycodone) (Hydroxycodone) (Hydroxycodone) (Hydroxycodone) (Hydroxycodone) (Hydroxycodone) (Hydroxycodone) (Hydroxycodone (Hydroxycodone) (Hydroxycodone) (Hydroxycodone) (Hydroxycodone (Hydroxy) (Hydroxycodone) (Hydroxycodone (Hydroxy) (Hydroxy) (Hydroxy) (Hydroxy) (Hydroxy) (Hydroxy F is 165 degrees. - What? ${\left(\alpha \right)}_D^{30}=-4°$ (c = 0,31; DMSO)

Example 140: The following substances are to be classified in the same category as the active substance:

By operating in a manner similar to example 2, the desired product is obtained as a white solid (yield = 39%) from the product prepared in accordance with example 139. F is 184 degrees. - What? ${\left(\alpha \right)}_D^{30}=-69°$ (c = 0,25; DMSO)

Example 141: 6- ((methyl-3-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to that in Example 137, 3-bromo-5-methylpyridine and 6-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IV are used to obtain the desired product as a white solid (yield = 38%). F = 189 to 190 degrees. - What? ${\left(\alpha \right)}_D^{25}=+9°$ (c = 0,20; DMSO)

Example 142: 6- ((methyl-3-pyridinyl) -3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner analogous to that of Example 42, the desired product is obtained as a white solid (yield = 49%) from the product prepared in accordance with Example 141. F = 165 to 166 degrees Celsius. - What? ${\left(\alpha \right)}_D^{30}=-44°$ (c = 0,25; DMSO)

Example 143: 5- ((methyl-3-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a similar way to example 137, starting from 3-bromo-5-methylpyridine, the desired product is obtained in the form of a beige solid (efficiency = 45%). F = 180 to 182 degrees. - What? ${\left(\alpha \right)}_D^{25}=-17°$ The concentration of the active substance in the test chemical is calculated as follows:

Example 144: 5- ((methyl-3-pyridinyl) -3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 42, the desired product is obtained as a white solid (yield = 83%) from the product prepared in accordance with Example 143. F = 119 to 120°C. - What? ${\left(\alpha \right)}_D^{25}=-73°$ (c = 0,27; DMSO)

Example 145: 5- ((chloro-3-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 1, the desired product is obtained as a white solid from 5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IX and 3-chloro-5- ((pinacolborane) pyridine (yield = 31%). F = 199 degrees. - What? ${\left(\alpha \right)}_D^{29}=-23°$ (c = 0,29; DMSO)

Example 146: 5- (chloro-3-pyridinyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 42, the desired product is obtained as a white solid (yield = 73%) from the product prepared in accordance with Example 145. F = 185 to 187 degrees. - What? ${\left(\alpha \right)}_D^{29}=-23°$ (c = 0,27; DMSO)

Example 147: 5- ((6-cyano-3-pyridinyl) -3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 1, the desired product is obtained from 5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IX and 6-cyano-3- ((pinacolborane) pyridine in the form of a purple solid (yield = 22%) F = 142 to 151 degrees Celsius. - What? ${\left(\alpha \right)}_D^{29}=-14°$ (c = 0,26; DMSO) is the mean value of the

Example 148: 5- ((6-cyano-3-pyridinyl) -3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to example 2, the desired product is obtained as a white solid (yield = 30%) from the product prepared in accordance with example 147. F = 197 to 203°C. - What? ${\left(\alpha \right)}_D^{29}=-68°$ (c = 0,34; DMSO) is the mean value of the

Example 149: 6- ((fluoro-3-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 1, the desired product is obtained as a white solid from 6-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IV and 3-fluoro-5- ((pinacolborane) pyridine (yield = 22%) F = 197 to 198 degrees. - What? ${\left(\alpha \right)}_D^{29}=+1°$ (c = 0,22; DMSO) is the mean value of the

Example 150: 6- ((fluoro-3-pyridinyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that in Example 2, the desired product is obtained as a white solid (yield = 66%) from the product prepared in accordance with Example 149. F = 207-217°C. - What? ${\left(\alpha \right)}_D^{29}=-56°$ (c = 0,21; DMSO)

Example 151: 5- ((2-methyl-3-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-xylopyranoside

By operating in a manner analogous to that in Example 137, 5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained from preparation IX and 2-methyl-3- ((pinacolborane) pyridine (obtained from 2-methyl-3-pyridinyl trifluoromethane sulphonate) are used to obtain the desired product in the form of a beige solid (yield = 30%). F = 152 to 153 degrees Celsius. - What? ${\left(\alpha \right)}_D^{29}=-21°$ (c = 0,24; DMSO)

Example 152: 5- ((2-methyl-3-pyridinyl) -3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner analogous to that of Example 42, the desired product is obtained as a white solid (yield = 85%) from the product prepared in accordance with Example 151. F = 204-207°C. - What? ${\left(\alpha \right)}_D^{29}=-81°$ (c = 0,21; DMSO)

Example 153: 5- (fluoro-3-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner similar to example 1, starting from 5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside and 3-fluoro-5-pinacolborane-pyridine, the desired product is obtained as a white solid (yield = 26%) F = 175 to 176 degrees Celsius. - What? ${\left(\alpha \right)}_D^{29}=-21°$ (c = 0,30; DMSO)

Example 154: 5- (fluoro-3-pyridinyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 42, the desired product is obtained as a white solid (yield = 77%). F = 160 to 171°C. - What? ${\left(\alpha \right)}_D^{29}=-72°$ (c = 0,25; DMSO)

Example 155: 6- ((Methoxy-3-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to that in Example 137, 3-bromo-5-methoxypyridine and 6-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IV are used to obtain the desired product as a white solid (yield = 48%). F is 155 degrees. - What? ${\left(\alpha \right)}_D^{29}=+1°$ (c = 0,47; DMSO)

Example 156: 6- ((Methoxy-3-pyridinyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that in Example 2, the desired product is obtained as a white solid (yield = 93%) from the product prepared in accordance with Example 155. F is 193 degrees. - What? ${\left(\alpha \right)}_D^{28}=-31°$ (c = 0,42; DMSO)

Example 157: The following substances are to be classified in the same category as the active substance:

By operating in a manner similar to example 1, the desired product is obtained as a white solid from 5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IX and 1,3,5-trimethyl-4- ((pinacolborane) pyrazole (yield = 60%). F is 166 degrees. - What? ${\left(\alpha \right)}_D^{29}=-26°$ (c = 0,19; DMSO)

Example 158: The following substances are to be classified in the same category as the active substance:

By operating in a manner similar to that in Example 2, the desired product is obtained as a white powder (yield = 48%) from the product prepared in accordance with Example 157. F is 174 degrees. - What? ${\left(\alpha \right)}_D^{29}=-82°$ (c = 0,27; DMSO)

Example 159: 5-(3,5-dimethyl-1H-pyrazol-4-yl)-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 1 from 5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IX and 3,5-dimethyl-4- ((pinacolborane) pyrazole, the desired product is obtained as a beige solid (yield = 45%). F = 95°C (crystallized in ether). - What? ${\left(\alpha \right)}_D^{29}=-22°$ (c = 0,24; DMSO)

Example 160: 5-(3,5-dimethyl-1H-pyrazol-4-yl)-3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that in Example 2, the desired product is obtained as a white powder (yield = 41%) from the product prepared in accordance with Example 159. F is 227 degrees. - What? ${\left(\alpha \right)}_D^{28}=-86°$ (c = 0,28; DMSO)

Example 161: 6- ((cyano-3-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 1 from 6-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IV and 6-cyano-3- ((pinacolborane) pyridine, the desired product is obtained as a white solid (yield = 41%). F is 247°C. - What? ${\left(\alpha \right)}_D^{29}=+15°$ (c = 0,20; DMSO)

Example 162: 6- ((cyano-3-pyridinyl) -3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to example 2, the desired product is obtained as a white solid (yield = 49%) from the product prepared in accordance with example 161. F is 167 degrees. - What? ${\left(\alpha \right)}_D^{27}=-43°$ (c = 0,30; DMSO)

Example 163: The following substances are to be classified in the same category as the active substance:

By operating in a manner analogous to example 1 from 6-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IV and 1,3,5-trimethyl-4- ((pinacolborane) -H-pyrazole, the desired product is obtained as a white solid (yield = 54%). F is 156 degrees. - What? ${\left(\alpha \right)}_D^{28}=0°$ (c = 0,24; DMSO)

Example 164: The following substances are to be classified in the same category as the active substance:

By operating in a manner similar to that in Example 2, the desired product is obtained as a white powder (yield = 57%) from the product prepared in accordance with Example 163. F is 132 degrees. - What? ${\left(\alpha \right)}_D^{28}=-41°$ (c = 0,29; DMSO)

Example 165: The following substances are to be classified in the same category as the active substance:

By operating in a manner analogous to example 1, the desired product is obtained as a white solid from 6-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IV and 1-methyl-4- ((pinacolborane) -H-pyrazole (yield = 46%). F is 183 degrees. - What? ${\left(\alpha \right)}_D^{28}=+7°$ (c = 0,18; DMSO) is the mean value of the

Example 166: The following substances are to be classified in the same category as the active substance:

By operating in a manner similar to example 2, the desired product is obtained as a white solid (yield = 65%) from the product prepared in accordance with example 165. - What? ${\left(\alpha \right)}_D^{28}=-50°$ (c = 0,20; DMSO)

Example 167: The following substances are to be classified in the same category as the active substance:

By operating in a manner analogous to example 1, the desired product is obtained as a white solid from 6-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IV and 3,5-dimethyl-4- ((pinacolborane) - 1H-pyrazole (yield = 21%) F is 154 degrees. - What? ${\left(\alpha \right)}_D^{28}=-1°$ (c = 0,26; DMSO) is the mean value of the

Example 168: The following substances are to be classified in the same category as the active substance:

By operating in a manner similar to that in Example 2, the desired product is obtained as a white solid (yield = 72%) from the product prepared in accordance with Example 167. F = 210°C. - What? ${\left(\alpha \right)}_D^{28}=-47°$ (c = 0,24; DMSO)

Example 169: 5- ((6-fluoro-3-pyridinyl) -3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 1, the desired product is obtained from 5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IX and 6-fluoro-3-pyridineboronic acid in the form of a solid cream (yield = 56%). F = 167-169 degrees. - What? ${\left(\alpha \right)}_D^{27}=-18°$ (c = 0,23; DMSO) is the mean value of the

Example 170: 5- ((6-fluoro-3-pyridinyl) -3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 124, the desired product is obtained as a white solid (yield = 47%) from the product prepared in accordance with Example 169. F = 210 to 212°C. - What? ${\left(\alpha \right)}_D^{24}=-47°$ (c = 0,14; DMSO)

Example 171: 5-1-methyl-1H-pyrazol-4-yl)-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 1, the desired product is obtained from 5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IX and 1-methyl-4- ((pinacolborane) -H-pyrazole in the form of a beige solid (yield = 58%). F is 68 degrees. - What? ${\left(\alpha \right)}_D^{29}=-19°$ (c = 0,20; DMSO)

Example 172: 5-methyl-1H-pyrazol-4-yl)-3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that in Example 2, the desired product is obtained as a white solid (yield = 72%) from the product prepared in accordance with Example 171. F is 216 degrees. - What? ${\left(\alpha \right)}_D^{29}=-74°$ (c = 0,25; DMSO)

Example 173: The following substances are to be classified in the same category as the active substance:

By operating in a manner analogous to example 1, the desired product is obtained from 6-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IV and 2,4-dimethyl-5- ((pinacolborane) thiazole in the form of white crystals (yield = 21%) F = 174-177°C (crystallized in ethyl ether). - What? ${\left(\alpha \right)}_D^{32}=+9°$ (c = 0,43; DMSO)

Example 174: The following substances are to be classified in the same category as the active substance:

By operating in a manner analogous to that in Example 42, the desired product is obtained in the form of cream crystals (yield = 92%) from the product prepared in accordance with Example 173. F is 175 degrees. - What? ${\left(\alpha \right)}_D^{32}=-53°$ (c = 0,41; DMSO)

Example 175: 6- ((2-methyl-3-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to that in Example 137, 6-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IV and 2-methyl-3- ((pinacolborane) pyridine (obtained from 2-methyl-3-pyridinyl trifluoromethanesulfonate) are used to obtain the desired product as a white solid (yield = 11%). F = 198 to 200 degrees Celsius. - What? ${\left(\alpha \right)}_D^{29}=-3°$ (c = 0,21; DMSO)

Example 176: 6- ((2-methyl-3-pyridinyl) -3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that in Example 2, the desired product is obtained as a white solid (yield = 39%) from the product prepared in accordance with Example 175. F = 167-168 degrees. - What? ${\left(\alpha \right)}_D^{32}=-26°$ (c = 0,32; DMSO) is the mean value of the

Example 177: 5- ((pyrimidinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

Mix 0,2 g (0.45 mM) of 5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained from preparation IX, 66 mg (0.53 mM) of 5-pyrimidine boronic acid, 0.281 g (0.90 mM) of grafted benzyl-triethylammonium carbonate resin and 36 mg (0.044 mM) of [1,1'-bisphenylphosphino) ferrocene]dichloropalladium (II) -dichloromethane in 3 ml of DME and 2 ml of methanol. Re-heat the mixture at 120°C by microwave for 30 minutes. After rinsing and solid crystallisation, the resulting product is reduced to a concentrated solution of naphthal chloride (70/30/g) to obtain a purified naphthal chloride (Chloroprol) chloride. F = 213-217°C. - What? ${\left(\alpha \right)}_D^{30}=-4°$ (c = 0,10; DMSO)

Example 178: 5- ((pyrimidinyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 42, the desired product is obtained in the form of a pink powder (yield = 67%) from the product prepared in accordance with Example 177. F = 196 degrees. - What? ${\left(\alpha \right)}_D^{30}=-96°$ (c = 0,17; DMSO)

Example 179: 5-(3,5-dimethyl-4-isoxazolyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner similar to that in Example 177, starting with 3,5-dimethyl-4-isoxazoleboronic acid, the desired product is obtained in the form of white crystals (efficiency = 33 %). F = 129-131°C. - What? ${\left(\alpha \right)}_D^{30}=-36°$ (c = 0,10; DMSO)

Example 180: 5-(3,5-dimethyl-4-isoxazolyl)-3-pyridinyl 5-thio-β-D-xylopyranoside, whether or not in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the solution in the form of a solution in the form of a solution in the solution in the form of a solution in the solution in the solution in the form of a solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in

By operating in a manner analogous to that in Example 42, the desired product is obtained in the form of white crystals (efficiency = 70%). F = 222-223°C. - What? ${\left(\alpha \right)}_D^{24}=-51°$ (c = 0,10; DMSO)

Example 181: 2-(3,5-dimethyl-4-isoxazolyl)-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner similar to that in Example 179, the desired product in the form of pink foam is obtained from 2-bromo-3-pyridinyl 5-thio-β-D-xylopyranoside obtained by preparation III (yield = 49%). F is 68-72 degrees. - What? ${\left(\alpha \right)}_D^{27}=-92°$ (c = 0,24; DMSO)

Example 182: 2-(3,5-dimethyl-4-isoxazolyl)-3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 42, the desired product is obtained as a broken white powder (efficiency = 65%) from the product prepared in accordance with Example 181. F is 112 degrees. - What? ${\left(\alpha \right)}_D^{27}=-53°$ (c = 0,24; DMSO)

Example 183: 5- ((2-fluoro-3-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a similar way to example 177, starting from 2-fluoro-3-pyridineboronic acid, the desired product is obtained in the form of beige crystals (efficiency = 52%). F = 169-170°C (recrystallized in isopropanol). - What? ${\left(\alpha \right)}_D^{24}=-37°$ (c = 0,17; DMSO)

Example 184: 5-(2-fluoro-3-pyridinyl)-3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that in Example 2, the desired product is obtained as a white solid (yield = 46%) from the product prepared in accordance with Example 183. F = 193 to 196 degrees. - What? ${\left(\alpha \right)}_D^{31}=-81°$ (c = 0,11; DMSO) is the mean value of the

Example 185: 5- ((2-fluoro-4-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to that in Example 177, starting from 2-fluoro-4-pyridineboronic acid, the desired product is obtained in the form of a beige solid (yield = 70%). F = 122-125°C. - What? ${\left(\alpha \right)}_D^{31}=-29°$ (c = 0,11; DMSO) is the mean value of the

Example 186: 5-(2-fluoro-4-pyridinyl)-3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that in Example 2, the desired product is obtained as a white solid (yield = 76%) from the product prepared in accordance with Example 185. F = 208°C (recrystallized in methanol). - What? ${\left(\alpha \right)}_D^{28}=-92°$ (c = 0,32; DMSO) is the mean value of the

Example 187: 6- ((2-fluoro-3-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner similar to that in Example 183, the desired product is obtained from 6-bromo-3-pyridinyl 5-thio-β-O-xylopyranoside obtained by preparation IV in the form of a cream powder (yield = 38%). F is 153 degrees. - What? ${\left(\alpha \right)}_D^{26}=-7°$ (c = 0,19; DMSO)

Example 188: 6- ((2-fluoro-3-pyridinyl) -3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that in Example 2, the desired product is obtained as a white powder (efficiency = 88%) from the product prepared in accordance with Example 187. F = 181 °C (recrystallized in water). - What? ${\left(\alpha \right)}_D^{27}=-48°$ (c = 0,17; DMSO)

Example 189:

6- ((5-pyrimidinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a similar way to example 187, starting with 5-pyrimidine boronic acid, the desired product is obtained in the form of a pink solid (yield = 39%). F = 215°C (crystallized in ethyl ether). - What? ${\left(\alpha \right)}_D^{28}=-2°$ (c = 0,18; DMSO) is the mean value of the

Example 190: 6- ((pyrimidinyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 42, the desired product is obtained in the form of a pink powder (efficiency = 77%). F is 188 degrees. - What? ${\left(\alpha \right)}_D^{27}=-45°$ (c = 0,19; DMSO)

Example 191: The following substances are to be classified in the same category as the active substance:

By operating in a manner analogous to that in Example 187, starting with 3,5-dimethyl-4-isoxazoleboronic acid, the desired product is obtained as a white solid (yield = 21%) F = 172°C (recrystallized in ethyl ether). - What? ${\left(\alpha \right)}_D^{28}=-13°$ The concentration of the active substance in the feed additive shall be calculated as follows:

Example 192:

The following substances are to be classified in the same category as the active substance:

By operating in a manner analogous to that in Example 42, the desired product is obtained as a white flaky solid (yield = 52%) from the product prepared in accordance with Example 191. F is 138 degrees. - What? ${\left(\alpha \right)}_D^{27}=-43°$ (c = 0,10; DMSO)

Example 193: 6- ((6-fluoro-3-pyridinyl) -3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to that in Example 187, starting with 6-fluoro-3-pyridineboronic acid, the desired product is obtained in the form of white flakes (yield = 30%). F = 185°C (recrystallized in an ethanol/water mixture). - What? ${\left(\alpha \right)}_D^{28}=+3°$ (c = 0,43; DMSO)

Example 194: 6- ((6-fluoro-3-pyridinyl) -3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that in Example 2, the desired product is obtained as a white powder (efficiency = 98%) from the product prepared in accordance with Example 193. F = 143 to 156 degrees Celsius. - What? ${\left(\alpha \right)}_D^{28}=-56°$ (c = 0,26; DMSO) is the mean value of the

Example 195: It consists predominantly of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

By operating in a manner similar to that in Example 177, starting from 5-bromo-2-fluoro-3-pyridinyl 5-thio-β-D-xylopyranoside obtained by preparation VIII and 2-fluoro-4-pyridineboronic acid, the desired product is obtained in the form of a pink solid (yield = 65%). F = 142-144°C. - What? ${\left(\alpha \right)}_D^{30}=-9°$ (c = 0,25; DMSO)

Example 196: It consists predominantly of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

By operating in a manner similar to that in Example 2, the desired product is obtained in the form of a grey solid (yield = 65%) from the product prepared in accordance with Example 195. F = 145 to 146 degrees Celsius. - What? ${\left(\alpha \right)}_D^{30}=+8°$ (c = 0,24; DMSO)

Example 197: 2-fluoro-5-(6-fluoro-3-pyridinyl)-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside, whether or not chemically defined

By operating in a manner similar to example 195, starting with 6-fluoro-3-pyridineboronic acid, the desired product is obtained in the form of a pink solid (yield = 35%). F = 135 to 136 degrees Celsius. - What? ${\left(\alpha \right)}_D^{30}=-22°$ (c = 0,28; DMSO)

Example 198: It consists predominantly of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

By operating in a manner similar to that in Example 2, the desired product is obtained in the form of a gray solid (yield = 71%) from the product prepared in accordance with Example 197. F = 158 to 159 degrees Celsius. - What? ${\left(\alpha \right)}_D^{30}=-72°$ (c = 0,30; DMSO)

Example 199: 5- (3-) thienyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to that in Example 177, starting with 3-thienylboronic acid, the desired product is obtained in the form of a beige solid (yield = 25%). F is 175 degrees. - What? ${\left(\alpha \right)}_D^{27}=+6°$ (c = 0,25; DMSO)

Example 200: 5- (3-) -thienyl-3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner analogous to that of Example 42, the desired product is obtained in the form of a white solid (yield = 32%) from the product prepared in accordance with Example 199. F is 212 degrees. - What? ${\left(\alpha \right)}_D^{27}=-113°$ (c = 0,10; DMSO)

Example 201: 6- ((2-chloro-4-pyridinyl) -3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner similar to that in Example 187, starting from 2-chloro-4-pyridineboronic acid, the desired product is obtained in the form of a pink powder (efficiency = 21%). F is 226 degrees. - What? ${\left(\alpha \right)}_D^{29}=+12°$ (c = 0,20; DMSO)

Example 202: The following substances are to be classified in the same category as the active substance:

By operating in a manner similar to example 2, the desired product is obtained as a yellow powder (efficiency = 62%) from the product prepared in accordance with example 201. F = 179°C (recrystallized in water). - What? ${\left(\alpha \right)}_D^{29}=-36°$ (c = 0,13; DMSO) is the mean value of the

Example 203: 4-(3,5-dimethyl-4-isoxazolyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner similar to that in Example 177, 4-bromo-3-pyridinyl 5-thio-β-D-xylopyranoside obtained by preparation II and 3,5-dimethyl-4-isoxazoleboronic acid are used to obtain the desired product in the form of a pink powder (efficiency = 30%). F = 150 to 155 degrees Celsius. - What? ${\left(\alpha \right)}_D^{25}=-38°$ (c = 0,10; DMSO)

Example 204: 4-(3,5-dimethyl-4-isoxazolyl)-3-pyridinyl 5-thio-β-D-xylopyranoside, whether or not in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the solution in the form of a solution in the solution in the form of a solution in the solution in the form of a solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in

By operating in a manner similar to that in Example 2, the desired product is obtained in the form of a beige powder (efficiency = 62%) from the product prepared in accordance with Example 203. F = 175 to 179 degrees. - What? ${\left(\alpha \right)}_D^{31}=-159°$ (c = 0,10; DMSO)

Example 205: The following substances are to be classified in the same category as the active substance:

By operating in a manner similar to that in Example 177, 2-iodo-6-methyl-3-pyridinyl 5-thio-β-D-xylopyranoside obtained by preparation V and 3-pyridineboronic acid are used to obtain the desired product in the form of an ochre powder (efficiency = 42%). F = 92 to 102 degrees. - What? ${\left(\alpha \right)}_D^{26}=-82°$ (c = 0,10; DMSO)

Example 206: The following substances are to be classified in the same category as the active substance:

By operating in a manner similar to that of Example 42, the desired product is obtained as a yellow powder (efficiency = 72%) from the product prepared in accordance with Example 205. F = 160 to 170°C. - What? ${\left(\alpha \right)}_D^{25}=-19°$ The concentration of the active substance in the feed additive shall be calculated on the basis of the following formula:

Example 207: The following substances are to be classified in the same category as the active substance:

By operating in a similar way to example 205, starting with 4-pyridinylboronic acid, the desired product is obtained as a pale pink powder (efficiency = 54%). F = 140 to 144 degrees Celsius. - What? ${\left(\alpha \right)}_D^{34}=-54°$ (c = 0,11; DMSO) is the mean value of the

Example 208: The following substances are to be classified in the same category as the active substance:

By operating in a manner similar to that of Example 42, the desired product is obtained in the form of a beige powder (efficiency = 95%) from the product prepared in accordance with Example 207. F = 196 to 200°C. - What? ${\left(\alpha \right)}_D^{25}=-35°$ (c = 0,10; DMSO)

Example 209: 6- ((2-fluoro-4-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to that in Example 187, starting from 2-fluoro-4-pyridineboronic acid, the desired product is obtained as a white solid (yield = 30%). F is 179 degrees. - What? ${\left(\alpha \right)}_D^{30}=+1°$ (c = 0.82; DMSO)

Example 210: 6- ((2-fluoro-4-pyridinyl) -3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 124, the desired product is obtained as a white solid (yield = 56%) from the product prepared in accordance with Example 209. F is 219 degrees. - What? ${\left(\alpha \right)}_D^{32}=-49°$ (c = 0,28; DMSO)

Example 211: 2- ((pyrimidinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner similar to example 181, starting with 5-pyrimidine boronic acid, the desired product is obtained in the form of a solid cream (yield = 48%). F = 205°C (recrystallized in ethyl ether). - What? ${\left(\alpha \right)}_D^{30}=-76°$ (c = 0,61; DMSO) is the mean value of the

Example 212: 2- ((pyrimidinyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 42, the desired product is obtained in the form of a pink powder (yield = 36%) from the product prepared in accordance with Example 211. F = 195°C (recrystallized in a methanol/ethyl ether mixture). - What? ${\left(\alpha \right)}_D^{30}=-38°$ The concentration of the active substance in the feed additive shall be calculated as follows:

Example 213: The following substances are to be classified in the same heading as the active substance:

A solution of 0.421 g (1 mM) of 6-chloro-5-fluoro-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained from preparation XI is prepared in 4 ml of DME. 0.211 g (1.5 mM) of 6-fluoro-3-pyridineboronic acid is added, 0.082 g (0.1 mM) of [1,1'-bisphenylephenolphosphino) dissolute]dichloropalladium (II) -dichloromethane is then dissolved in 1.5 ml (1.5 mM) of a 1 M solution of potassium carbonate. The reaction is heated to 120 °C under 30 min by micro-water extraction. After cooling and decomposition, the evaporant is used in the current phase and dissolved in a mixture of organic phenol and potassium phosphatase. The product is then dissolved directly in the membrane and 1 ml of organic phosphates are added to the solution and dissolved in the water.

Example 214: It consists of a mixture of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

By operating in a manner similar to that in Example 2, the desired product is obtained as a white solid with a yield of 75% from the product prepared in accordance with Example 213. F is 184 degrees. - What? ${\left(\alpha \right)}_D^{33}=-54°$ (c = 0,10; DMSO)

Example 215: 5-fluoro-6- ((6-methyl-3-pyridinyl) -3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 213, starting from 6-methyl-3-pyridineboronic acid, the desired product is obtained which is directly used in the deacetylation step.

Example 216: 5-fluoro-6- ((6-methyl-3-pyridinyl) -3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that in Example 2, the desired product is obtained as a white solid (yield = 58%) from the product prepared in accordance with Example 215. F is 184 degrees. - What? ${\left(\alpha \right)}_D^{33}=-54°$ (c = 0,24; DMSO)

Example 217: 5- ((2-Methoxy-5-pyrimidinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to that in Example 213, 5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IX and 2-methoxy-5-pyrimidine boronic acid are obtained to produce the desired product which is directly used in the deacetylation step.

Example 218: 5- ((2-methoxy-5-pyrimidinyl) -3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that in Example 2, the desired product is obtained as a white solid (yield = 46%) from the product prepared in accordance with Example 217. F is 215 degrees. - What? ${\left(\alpha \right)}_D^{30}=-75°$ (c = 0,10; DMSO)

Example 219: 5-fluoro-6-(2-methyl-4-pyridinyl)-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 213, starting from 2-methyl-4-pyridineboronic acid, the desired product is obtained which is directly used in the deacetylation step.

Example 220: 5-fluoro-6-(2-methyl-4-pyridinyl)-3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that in Example 2, the desired product is obtained as a white solid (yield = 31%) from the product prepared in accordance with Example 219. F is 143 degrees. - What? ${\left(\alpha \right)}_D^{30}=-27°$ (c = 0,10; DMSO)

Example 221: 5-fluoro-6-(2-methoxy-3-pyridinyl)-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside, whether or not chemically defined

By operating in a manner analogous to example 213, starting from 2-methoxy-3-pyridineboronic acid, the desired product is obtained which is directly used in the deacetylation step.

Example 222: 5-fluoro-6-(2-methoxy-3-pyridinyl)-3-pyridinyl 5-thio-β-D-xylopyranoside, whether or not in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the solution in the form of a solution in the solution in the form of a solution in the solution in the form of a solution in the solution in the solution in the form of a solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation

By operating in a manner similar to that in Example 2, the desired product is obtained as a white solid (yield = 77%) from the product prepared in accordance with Example 221. F is 141 degrees. - What? ${\left(\alpha \right)}_D^{30}=-35°$ (c = 0,10; DMSO)

Example 223: The following substances are to be classified in the same category as the active substance:

By operating in a manner analogous to example 213, starting from 1-methyl-4- ((pinacolborane) - 1H-pyrazole, the desired product is obtained which is directly used in the deacetylation step.

Example 224: The following substances are to be classified in the same category as the active substance:

By operating in a manner similar to that in Example 2, the desired product is obtained as a white solid (yield = 41%) from the product prepared in accordance with Example 223. F is 206 degrees Celsius. - What? ${\left(\alpha \right)}_D^{30}=-46°$ (c = 0,10; DMSO)

Example 225: The following substances are to be classified in the same category as the active substance:

By operating in a manner analogous to example 213, starting from 3,5-dimethyl-4-isoxazoleboronic acid, the desired product is obtained which is directly used in the deacetylation step.

Example 226: The following substances are to be classified in the same category as the active substance:

By operating in a manner similar to that in Example 2, the desired product is obtained as a white solid (yield = 33%) from the product prepared in accordance with Example 225. F = 177 degrees. - What? ${\left(\alpha \right)}_D^{30}=-48°$ (c = 0,12; DMSO) is the mean value of the

Example 227: The following substances are to be classified in the same category as the active substance:

By operating in a manner analogous to that in Example 213, 6-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IV and 2-methoxy-5-pyrimidine boronic acid are obtained to produce the desired product which is directly used in the deacetylation step.

Example 228: The following substances are to be classified in the same category as the active substance:

By operating in a manner similar to that in Example 2, the desired product is obtained as a white solid (yield = 20%) from the product prepared in accordance with Example 227. F is 134 degrees. - What? ${\left(\alpha \right)}_D^{26}=-53°$ (c = 0,10; DMSO)

Example 229: 5-fluoro-6- ((5-pyrimidinyl) -3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 213, starting from 5-pyrimidine boronic acid, the desired product is obtained which is directly used in the deacetylation step.

Example 230: The following substances are to be classified in the same category as the active substance:

By operating in a manner analogous to example 2, the desired product is obtained as a white solid (yield = 19%) from the product prepared in accordance with example 229. F is 192 degrees. - What? ${\left(\alpha \right)}_D^{33}=-34°$ (c = 0,12; DMSO) is the mean value of the

Example 231: 5- (3-chloro-2-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

From a 0.448 g (1 mM) solution of 5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IX in 2 ml of DME, the boronate is prepared by the method described in example 49. The reaction medium is then filtered and rinsed with DME. The resulting solution is then to be added 0.422 g (1.66 mM) of 2,3-dichloropyridine, 0.020 g (0.025 mM) of [1,1bis diphenylphosphino) desyphenol]dichloropalladium II] then dissolved in water. The 1.5 mM of a solution of 1M of current potassium chloride is used. The reaction medium is then evaporated in a 30°C phase of organic distillation of phenol and methanol. After the reaction phase, the product is dissolved in water and then reduced to 1 mL of organic distillate and distillate.

Example 232 5- (3-chloro-2-pyridinyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 2, the desired product is obtained as a white solid (yield = 50%) from the product prepared in accordance with example 231. F = 193°C - What? ${\left(\alpha \right)}_D^{30}=-46°$ (c = 0,18; DMSO) is the mean value of the

Example 233: 5- ((methyl-2-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 231, starting from 2-bromo-5-methylpyridine, the desired product is obtained which is directly used in the deacetylation step.

Example 234: 5- ((methyl-2-pyridinyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that in Example 2, the desired product is obtained as a white solid (yield = 33%) from the product prepared in accordance with Example 233. F = 199 degrees. - What? ${\left(\alpha \right)}_D^{29}=-64°$ (c = 0,18; DMSO) is the mean value of the

Example 235: 5- ((methyl-2-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 231, starting from 2-bromo-4-methylpyridine, the desired product is obtained which is directly used in the deacetylation step.

Example 236: 5-methyl-2-pyridinyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that in Example 2, the desired product is obtained as a white powder (yield = 20%), starting with the product prepared in accordance with Example 235. F is 166 degrees. - What? ${\left(\alpha \right)}_D^{29}=-80°$ (c = 0,10; DMSO)

Example 237: 5- ((6-methyl-2-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 231, starting from 2-bromo-6-methylpyridine, the desired product is obtained which is directly used in the deacetylation step.

Example 238: 5- ((6-methyl-2-pyridinyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that in Example 2, the desired product is obtained as a white powder (efficiency = 49%) from the product prepared in accordance with Example 237. F is 188 degrees. - What? ${\left(\alpha \right)}_D^{29}=-68°$ (c = 0,30; DMSO)

Example 239: The following substances are to be classified in the same category as the active substance:

Mix 0.3 g (0.59 mM) of 2-iodo-6-methyl-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation V, 0.1 g (0.71 mM) of 3,5-dimethyl-4-isoxazoleboronic acid, 0.384 g (1.17 mM) of caesium carbonate and 0.327 g of tetracycline triphenylphosphine) palladium grafted onto polystyrene resin in ml of DME and 3,5 ml of methanol. Heat at 120°C for 30 minutes with a microwave. The mixture is then evaporated, the residual solid is converted to methanol and the filtrate is concentrated. The residual is reduced to a white colour by means of a chromograph to give a colour filter (80/20/%) with a thiol-methyl chloride filter. F = 70 to 84 degrees. - What? ${\left(\alpha \right)}_D^{31}=-64°$ (c = 0,11; DMSO) is the mean value of the

Example 240: 2- ((6-fluoro-3-pyridinyl) -3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that in Example 239, the desired product is obtained from 2-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation III and 6-chloro-3-pyridineboronic acid in the form of a white powder (yield = 14%). F = 199 degrees. - What? ${\left(\alpha \right)}_D^{32}=-54°$ (c = 0,26; DMSO) is the mean value of the

Example 241: 2-(3,5-dimethyl-4-isoxazolyl)-4-pyridinyl 5-thio-β-D-xylopyranoside, whether or not in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the solution in the form of a solution in the solution in the form of a solution in the solution in the form of a solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in

By operating in a manner similar to that described in example 239, the desired product is obtained from 2-bromo-4-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation VII and 3,5-dimethyl-4-isoxazoleboronic acid in the form of white crystals (efficiency = 25%). F = 143-147°C (recrystallized in water). - What? ${\left(\alpha \right)}_D^{27}=-77°$ (c = 0,22; DMSO) is the mean value of the

Example 242: 5- ((4-methoxy-3-pyridinyl) -3-pyridinyl 5-thio-β-D-xylopyranoside)

By operating in a manner analogous to that described in example 239, the desired product is obtained from 5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IX and 4-methoxy-3-pyridineboronic acid in the form of a white solid (yield = 23%). F is 154 degrees. - What? ${\left(\alpha \right)}_D^{29}=-49°$ (c = 0,30; DMSO)

Example 243: 6- ((4-methoxy-3-pyridinyl) -3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that described in example 239, the desired product is obtained from 6-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IV and 4-methoxy-3-pyridineboronic acid in the form of a white solid (yield = 37%). F = 207 degrees. - What? ${\left(\alpha \right)}_D^{27}=-11°$ (c = 0,25; DMSO)

Example 244: 5- ((2-methyl-4-pyridinyl) -3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner analogous to that described in example 239, the desired product is obtained from 5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IX and 2-methyl-4-pyridineboronic acid in the form of a white solid (yield = 28%). F = 120°C (recrystallized in water). - What? ${\left(\alpha \right)}_D^{29}=-77°$ (c = 0,17; DMSO)

Example 245: 6- ((2-methyl-4-pyridinyl) -3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that in Example 239, 6-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IV and 2-methyl-4-pyridineboronic acid are used to obtain the desired product as a white powder (efficiency = 23%). F = 214°C (recrystallized in water). - What? ${\left(\alpha \right)}_D^{28}=-51°$ (c = 0,52; DMSO)

Example 246: 6- ((5-chloro-3-pyridinyl) -3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 1, the desired product is obtained as a white solid from 6-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation IV and 5-chloro-3-pyridineboronic acid (yield = 40%). F = 203-205°C. The temperature is the temperature of the air. - What? ${\left(\alpha \right)}_D^{30}=+8°$ (c = 0,31; DMSO)

Example 247: The following substances are to be classified in the same category as the active substance:

By operating in a manner analogous to that of Example 42, the desired product is obtained as a white solid (yield = 28%) from the product prepared in accordance with Example 246. F = 171-172°C. - What? ${\left(\alpha \right)}_D^{30}=-167°$ (c = 0,24; DMSO)

Example 248: 5- ((methyl-3-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 137, starting from 3-bromo-4-methylpyridine, the desired product is obtained as a white solid (yield = 9%). F is 165 degrees. - What? ${\left(\alpha \right)}_D^{30}=-9°$ The concentration of the active substance in the feed additive shall be calculated as follows:

Example 249: 5-methyl-3-pyridinyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that in Example 2, the desired product is obtained as a white solid (yield = 49%) from the product prepared in accordance with Example 248. F = 201 °C. - What? ${\left(\alpha \right)}_D^{26}=-75°$ (c = 0,23; DMSO) is the mean value of the

Example 250: 2,6-di-di-fluoro-pyridinyl) -3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside, whether or not in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the solution in the form of a solution in the form of a solution in the solution in the form of a solution in the solution in the form of a solution in the solution in the solution in the form of a solution in the solution in the solution in the solution in the form of a solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in

By operating in a manner similar to example 1, the desired product is obtained from 2-chloro-6-iodo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation X and 6-fluoro-3-pyridineboronic acid in the form of a beige powder (yield = 15%). F is 169 degrees. - What? ${\left(\alpha \right)}_D^{26}=-35°$ (c = 0,45; DMSO)

Example 251: 2,6-di-di-fluoro-pyridinyl) 3-pyridinyl 5-thio-β-D-xylopyranoside, whether or not in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the solution in the form of a solution in the form of a solution in the solution in the form of a solution in the solution in the form of a solution in the solution in the solution in the solution in the form of a solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation.

By operating in a manner similar to example 2, the desired product is obtained in the form of a beige powder (yield = 30%). F = 209°C (recrystallized in an ethanol/water mixture). - What? ${\left(\alpha \right)}_D^{26}=-19°$ (c = 0,14; DMSO)

Example 252: 2-tetrazolyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

A mixture of 0.682 g (1.73 mM) of 2-cyano-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained from XV and 1.24 g (6.05 mM) of azidotrimethylen in 10 ml of toluene is prepared and stirred for 7 days at 70°C. After cooling, the reaction medium is poured over a mixture of water and ethyl acetate and brought to pH 1 by adding a solution N of hydrochloric acid. The aqueous phase is separated to pH 5 by adding a dilute solution of solvent and extracted by moisture from the organic compound ethyl acetate. This phase, separated by washing, is obtained in the form of a white solution of sulphate obtained by a concentrated solution of magnesium dichloride (9/5/molybdenum) and obtained by pressurizing the product with a thin layer of white water. F = 119 to 127 degrees. - What? ${\left(\alpha \right)}_D^{25}=-147°$ (c = 0,28; CH2Cl2) The following is the solution:

Example 253: 2-tetrazolyl) 3-pyridinyl 5-thio-β-D-xylopyranoside

By operating in a manner similar to that of Example 42, the desired product is obtained as a white powder (yield = 42%) from the product prepared in accordance with Example 252. F = 170°C (recrystallized in an ethanol/water mixture). - What? ${\left(\alpha \right)}_D^{22}=-153°$ (c = 0,24; DMSO)

Example 254: The following substances are to be classified in the same category as the active substance:

By operating in a manner analogous to that in Example 213, 2-fluoro-6-iodo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation XII and 3,5-dimethyl-4-isoxazoleboronic acid are obtained to obtain the desired product which is directly used in the deacetylation step.

Example 255: The following substances are to be classified in the same category as the active substance:

By operating in a manner similar to that in Example 2, the desired product is obtained as a white powder (yield = 56%) from the product prepared in accordance with Example 254. F = 101 to 104 degrees Celsius. - What? ${\left(\alpha \right)}_D^{32}=-42°$ (c = 0,12; DMSO) is the mean value of the

Example 256: It consists predominantly of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

By operating in a manner analogous to example 254, starting from 2-fluoro-3-pyridineboronic acid, the desired product is obtained which is directly used in the deacetylation step.

Example 257: It consists predominantly of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

By operating in a manner similar to that in Example 2, the desired product is obtained as a white powder (yield = 53%) from the product prepared in accordance with Example 256. F = 186 to 190 degrees. - What? ${\left(\alpha \right)}_D^{32}=-33°$ (c = 0,12; DMSO) is the mean value of the

Example 258: 2-fluoro-6- ((5-pyrimidinyl) -3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 254, starting from 5-pyrimidine boronic acid, the desired product is obtained which is directly used in the deacetylation step.

Example 259: The following substances are to be classified in the same heading as the active substance:

By operating in a manner similar to that in Example 2, the desired product is obtained as a white powder (yield = 33%). F = 177 to 179 degrees. - What? ${\left(\alpha \right)}_D^{32}=-106°$ (c = 0,45; DMSO)

Example 260: 2-fluoro-6-(6-fluoro-3-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 254, 6-fluoro-3-pyridineboronic acid is used to produce the desired product which is directly used in the deacetylation step.

Example 261: It consists predominantly of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

By operating in a manner similar to that in Example 2, the desired product is obtained as a white powder (efficiency = 65%) from the product prepared in accordance with Example 260. F = 141-144°C. - What? ${\left(\alpha \right)}_D^{32}=-38°$ (c = 0,26; DMSO) is the mean value of the

Example 262: It consists predominantly of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

By operating in a manner analogous to example 254, starting from 2-fluoro-4-pyridineboronic acid, the desired product is obtained which is directly used in the deacetylation step.

Example 263: It consists of a mixture of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

By operating in a manner similar to that in Example 2, the desired product is obtained as a white powder (yield = 53%) from the product prepared in accordance with Example 262. F = 179 to 182 degrees. - What? ${\left(\alpha \right)}_D^{32}=-37°$ (c = 0,10; DMSO)

Example 264: 2-fluoro-6-(1-methyl-1H-pyrazol-4-yl)-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 254, starting from 1-methyl-4- ((pinacolborane) - 1H-pyrazole, the desired product is obtained which is directly used in the deacetylation step.

Example 265: The following substances are to be classified in the same category as the active substance:

By operating in a manner similar to that in Example 2, the desired product is obtained as a white solid (yield = 38%) from the product prepared in accordance with Example 264. F = 183-185 degrees. - What? ${\left(\alpha \right)}_D^{32}=-23°$ (c = 0,13; DMSO) is the mean value of the

Example 266: 2-fluoro-6- ((6-methyl-3-pyridinyl) -3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 254, starting from 6-methyl-3-pyridineboronic acid, the desired product is obtained which is directly used in the deacetylation step.

Example 267: It consists predominantly of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

By operating in a manner similar to that in Example 2, the desired product is obtained in the form of a pink powder (yield = 36%) from the product prepared in accordance with Example 266. F = 189 to 190 degrees. - What? ${\left(\alpha \right)}_D^{32}=-20°$ (c = 0,10; DMSO)

Example 268: 2-fluoro-6-(2-methyl-4-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to example 254, starting from 2-methyl-4-pyridineboronic acid, the desired product is obtained which is directly used in the deacetylation step.

Example 269: It consists of a mixture of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

By operating in a manner similar to that in Example 2, the desired product is obtained as a white powder (yield = 24%) from the product prepared in accordance with Example 268. F = 159 to 162 degrees Celsius. - What? ${\left(\alpha \right)}_D^{32}=-23°$ (c = 0,10; DMSO)

Example 270: 2-fluoro-6-(6-cyano-3-pyridinyl)-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a similar manner to example 254, starting from 2-cyano-5- ((pinacolborane) -pyridine, the desired product is obtained which is directly used in the deacetylation step.

Example 271: It consists predominantly of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

By operating in a manner similar to that in Example 2, the desired product is obtained as a white powder (yield = 37%) from the product prepared in accordance with Example 270. F = 158 to 162 degrees Celsius. - What? ${\left(\alpha \right)}_D^{32}=-19°$ (c = 0,14; DMSO)

Example 272: 5-fluoro-6-(3-pyridinyl) 3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to that in Example 213, 6-chloro-5-fluoro-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation XI and 3-pyridineboronic acid are obtained to produce the desired product which is directly used in the deacetylation step.

Example 273: The following substances are to be classified in the same heading as the active substance:

By operating in a manner similar to that in Example 2, the desired product is obtained as a white powder (yield = 58%) from the product prepared in accordance with Example 272. F is 179 degrees. - What? ${\left(\alpha \right)}_D^{32}=-33°$ (c = 0,10; DMSO)

Example 274: The following substances are to be classified in the same heading as the active substance:

By operating in a manner analogous to example 272, starting from 2-fluoro-4-pyridineboronic acid, the desired product is obtained which is directly used in the deacetylation step.

Example 275: The following substances are to be classified in the same heading as the active substance:

By operating in a manner similar to that in Example 2, the desired product is obtained as a white powder (yield = 53%) from the product prepared in accordance with Example 274. F = 209-212°C. - What? ${\left(\alpha \right)}_D^{27}=-68°$ (c = 0,10; DMSO)

Example 276: 2-chloro-5-(5-pyrimidinyl)-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside, whether or not in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the solution in the form of a solution in the form of a solution in the solution in the form of a solution in the solution in the form of a solution in the solution in the solution in the form of a solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation

By operating in a manner analogous to that in Example 259, the expected product in the form of a white foam is obtained from 5-bromo-2-chloro-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation XIV (yield = 48%). F = 72-90 °C. - What? ${\left(\alpha \right)}_D^{25}=-44°$ (c = 0,21; DMSO)

Example 277: The following substances are to be classified in the same heading as the active substance:

By operating in a manner analogous to example 2, the desired product is obtained in the form of white flakes (yield = 81%). F = 174 to 189 degrees. - What? ${\left(\alpha \right)}_D^{25}=60°$ (c = 0,22; DMSO) is the mean value of the

Example 278: 2-chloro-5-(6-fluoro-3-pyridinyl)-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside, whether or not chemically defined

By operating in a manner analogous to that in Example 276, starting from 6-fluoro-3-pyridineboronic acid, the expected product is obtained as a white foam (yield = 38%). F = 70-90 °C. - What? ${\left(\alpha \right)}_D^{24}=-26°$ (c = 0,22; DMSO) is the mean value of the

Example 279: It consists predominantly of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

By operating in a manner similar to example 2, the desired product is obtained in the form of white flakes (yield = 84%) from the product prepared in accordance with example 278. F = 176 to 197 degrees. - What? ${\left(\alpha \right)}_D^{30}=-51°$ (c = 0,15; DMSO)

Example 280: 2-chloro-6- ((5-pyrimidinyl) -3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

By operating in a manner analogous to that in Example 259, the expected product in the form of a white foam is obtained from 2-chloro-6-iodo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained by preparation X (yield = 37%). F = 168 °C. - What? ${\left(\alpha \right)}_D^{36}=-41°$ The concentration of the active substance in the feed additive shall be calculated on the basis of the following formula:

Example 281: The following substances are to be classified in the same heading as the active substance:

By operating in a manner similar to that in Example 2, the desired product is obtained as a white powder (yield = 20%), starting with the product prepared in accordance with Example 280. F is 100°C. - What? ${\left(\alpha \right)}_D^{26}=31°$ (c = 0,11; DMSO) is the mean value of the

Example 282: It consists predominantly of hydrocarbons having carbon numbers predominantly in the range of C1 through C5.]

By operating in a manner analogous to example 231, 5-bromo-2-fluoro-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained from preparation VIII and 2-bromopyridine is obtained to produce the desired product which is directly used in the deacetylation step.

Example 283: The following substances are to be classified in the same heading as the active substance:

By operating in a manner similar to that in Example 2, the desired product is obtained as a white solid (yield = 79%) from the product prepared in accordance with Example 282. F = 145 to 146 degrees Celsius.

Example 284: 2-fluoro-5-(5-pyrimidinyl)-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside, whether or not in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the form of a solution in the solution in the form of a solution in the form of a solution in the solution in the form of a solution in the solution in the form of a solution in the solution in the solution in the form of a solution in the solution in the solution in the solution in the solution in the form of a solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the solution in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation in the situation

By operating in a manner analogous to the first part of Example 137, 5-bromopyrimidine is prepared from 5- ((pinacolborane) pyrimidine, which is immediately reacted in the same reactor with 5-bromo-2-fluoro-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained from Preparation VIII under conditions similar to those applied for the preparation of Example 177. The expected product is thus obtained as a yellow solid (efficiency = 40%). F = 96-97 °C. - What? ${\left(\alpha \right)}_D^{30}=-11°$ (c = 0.24; DMSO) is the mean of the

Example 285: The following substances are to be classified in the same heading as the active substance:

By operating in a manner analogous to that in Example 2, the desired product is obtained as a white solid (yield = 60%) from the product prepared in accordance with Example 284.

F = 204 to 205°C.

The structures of the formula 1 compounds described in the examples above have been grouped in the following table: - What?

Ex	Pos -N	R'	R"	Pos-A	A								R
					X	Y	Z1	Z2	Z3
1	3	H	H	6	3-N	C	C	C	C		H	H	Ac
2	3	H	H	6	3-N	C	C	C	C		H	H	H
3	3		H	2	3-N	C	C	C	C	H	H	H	Ac
4	3		H	2	3-N	C	C	C	C	H	H	H	H
5	3		H	2	3-O	ls	C	C	C	H	H	H	Ac
6	3		H	2	3-O	ls	C	C	C	H	H	H	H
7	3	H	H	2	2-O	ls	C	C	C		H	H	Ac
8	3	H	H	2	2-O	ls	C	C	C		H	H	H
9	3	2-Cl	H	6	3-N	C	C	C	C	H	H	H	Ac
10	3	2-Cl	H	6	3-N	C	C	C	C	H	H	H	H
11	3	2-F	H	5	4-N	C	C	C	C	H	H	H	Ac
12	3	2-F	H	5	4-N	C	C	C	C	H	H	H	H
13	3	2-Cl	H	6	3-N	C	C	C	C		H	H	Ac
14	3	2-Cl	H	6	3-N	C	C	C	C		H	H	H
15	3	2-Cl	H	6	3-N	C	C	C	C	2-F	H	H	Ac
16	3	2-Cl	H	6	3-N	C	C	C	C	2-F	H	H	H
17	3	2-Cl	H	6	4-N	C	C	C	C	2-F	H	H	Ac
18	3	2-Cl	H	6	4-N	C	C	C	C	2-F	H	H	H
19	3	2-Cl	H	6	3-N	C	C	C	C	6-F	H	H	Ac
20	3	2-Cl	H	6	3-N	C	C	C	C	6-F	H	H	H
21	3	2-F	H	6	4-N	C	C	C	C	H	H	H	Ac
22	3	2-F	H	6	4-N	C	C	C	C	H	H	H	H
23	3	2-Cl	H	6	4-N	C	C	C	C	H	H	H	Ac
24	3	2-Cl	H	6	4-N	C	C	C	C	H	H	H	H
25	3	H	H	5	3-N	C	C	C	C	2-Cl	H	H	Ac
26	3	H	H	5	3-N	C	C	C	C	2-Cl	H	H	H
27	3	H	H	5	3-N	C	C	C	C		H	H	Ac
28	3	H	H	5	3-N	C	C	C	C		H	H	H
29	3	H	H	5	3-N	C	C	C	C	6-Cl	H	H	Ac
30	3	H	H	5	3-N	C	C	C	C	6-Cl	H	H	H
31	3	H	H	5	3-N	C	C	C	C		H	H	Ac
32	3	H	H	5	3-N	C	C	C	C		H	H	H
33	3	H	H	6	2-O	ls	C	C	C		H	H	Ac
34	3	H	H	6	2-O	ls	C	C	C		H	H	H
35	3	H	H	6	3-N	C	C	C	C		H	H	Ac
36	3	H	H	6	3-N	C	C	C	C		H	H	H
37	3	H	H	6	3-N	C	C	C	C	6-Cl	H	H	Ac
38	3	H	H	6	3-N	C	C	C	C	6-Cl	H	H	H
39	3	H	H	6	3-N	C	C	C	C	2-Cl	H	H	Ac
40	3	H	H	6	3-N	C	C	C	C	2-Cl	H	H	H
41	3	5-Cl	H	6	4-N	C	C	C	C	H	H	H	Ac
42	3	5-Cl	H	6	4-N	C	C	C	C	H	H	H	H
43	3	5-F	H	6	4-N	C	C	C	C	H	H	H	Ac
44	3	5-F	H	6	4-N	C	C	C	C	H	H	H	H
45	2	H	H	6	4-N	C	C	C	C	H	H	H	Ac
46	2	H	H	6	4-N	C	C	C	C	H	H	H	H
47	2	H	H	6	3-N	C	C	C	C	H	H	H	Ac
48	2	H	H	6	3-N	C	C	C	C	H	H	H	H
49	3	H	H	5	2-N	C	C	C	C	5-F	H	H	Ac
50	3	H	H	5	2-N	C	C	C	C	5-F	H	H	H
51	3	2-F	H	5	3-N	C	C	C	C	H	H	H	Ac
52	3	2-F	H	5	3-N	C	C	C	C	H	H	H	H
53	3	H	H	5	4-N	C	C	C	C		H	H	Ac
54	3	H	H	5	4-N	C	C	C	C		H	H	H
55	3	H	H	5	2-N	C	C	C	C		H	H	Ac
56	3	H	H	5	2-N	C	C	C	C		H	H	H
57	3	H	H	5	5-S	ls	C	N	C			-	Ac
58	3	H	H	5	5-S	ls	C	N	C			-	H
59	3	H	H	5	4-N	ls	N	C	C			H	Ac
60	3	H	H	5	4-N	ls	N	C	C			H	H
61	3	H	H	5	4-N	ls	N	C	C			H	Ac
62	3	H	H	5	4-N	ls	N	C	C			H	H
63	3	H	H	5	4-O	ls	N	C	C		H	-	Ac
64	3	H	H	5	4-O	ls	N	C	C		H	-	H
65	3	H	H	5	2-N	C	C	N	C	H	H	H	Ac
66	3	H	H	5	2-N	C	C	N	C	H	H	H
67	3	H	H	5	2-N	C	N	C	C	H	H	H	Ac
68	3	H	H	5	2-N	C	N	C	C	H	H	H	H
69	3	H	H	5	2-S	ls	C	N	C	H	H	-	Ac
70	3	H	H	5	2-S	ls	C	N	C	H	H	-	H
71	3	H	H	5	5-N	ls	C	N	C		H	H	Ac
72	3	H	H	5	5-N	ls	C	N	C		H	H	H
73	3	H	H	5	4-N	C	C	C	C	2-Cl	H	H	Ac
74	3	H	H	5	4-N	C	C	C	C	2-Cl	H	H	H
75	3	H	H	5	4-N	C	C	C	C	3-Cl	H	H	Ac
76	3	H	H	5	4-N	C	C	C	C	3-Cl	H	H	H
77	3	H	H	6	3-N	C	C	C	C		H	H	Ac
78	3	H	H	6	3-N	C	C	C	C		H	H	H
79	3		H	2	3-O	ls	C	C	C	H	H	H	Ac
80	3		H	2	3-O	Is	C	C	C	H	H	H	H
81	3		H	2	4-O	ls	N	C	C			-	Ac
82	3		H	2	4-O	ls	N	C	C			-	H
83	3	H	H	4	3-N	C	C	C	C	H	H	H	Ac
84	3	H	H	4	3-N	C	C	C	C	H	H	H	H
85	3	H	H	2								H	Ac
86	3	H	H	2								H	H
87	3	H	H	4	3-O	ls	C	C	C	H	H	H	Ac
88	3	H	H	4	3-O	ls	C	C	C	H	H	H	H
89	3	H	H	4	4-N	C	C	C	C	H	H	H	Ac
90	3	H	H	4	4-N	C	C	C	C	H	H	H	H
91	3	H	H	5								H	Ac
92	3	H	H	5								H	H
93	3	H	H	2	2-S	ls	C	C	C	H	H	H	Ac
94	3	H	H	2	2-S	ls	C	C	C	H	H	H	H
95	3	H	H	5	2-O	ls	C	C	C		H	H	Ac
96	3	H	H	5	2-O	ls	C	C	C		H	H	H
97	3	H	H	6								H	Ac
98	3	H	H	6								H	H
99	3	H	H	6	3-S	ls	C	C	C	H	H	H	Ac
100	3	H	H	6	3-S	ls	C	C	C	H	H	H	H
101	3	H	H	2	2-O	ls	C	C	C	H	H	H	Ac
102	3	H	H	2	2-O	ls	C	C	C	H	H	H	H
103	3	H	H	6	2-O	ls	C	C	C	H	H	H	Ac
104	3	H	H	6	2-O	Is	C	C	C	H	H	H	H
105	3	H	H	2	4-N	C	C	C	C	H	H	H	Ac
106	3	H	H	2	4-N	C	C	C	C	H	H	H	H
107	3	H	H	6	2-S	ls	C	C	C	H	H	H	Ac
108	3	H	H	6	2-S	ls	C	C	C	H	H	H	H
109	3	H	H	5	2-O	ls	C	C	C	H	H	H	Ac
110	3	H	H	5	2-O	ls	C	C	C	H	H	H	H
111	3	H	H	2	3-N	C	C	C	C	H	H	H	Ac
112	3	H	H	2	3-N	C	C	C	C	H	H	H	H
113	3	H	H	2	3-O	ls	C	C	C	H	H	H	Ac
114	3	H	H	2	3-O	ls	C	C	C	H	H	H	H
115	3	H	H	5								H	Ac
116	3	H	H	5								H	H
117	3	H	H	6	3-O	ls	C	C	C	H	H	H	Ac
118	3	H	H	6	3-O	ls	C	C	C	H	H	H	H
119	3	H	H	6	3-N	C	C	C	C	H	H	H	Ac
120	3	H	H	6	3-N	C	C	C	C	H	H	H	H
121	3	H	H	6	4-N	C	C	C	C	H	H	H	Ac
122	3	H	H	6	4-N	C	C	C	C	H	H	H	H
123	3	H	H	5	4-N	C	C	C	C	H	H	H	Ac
124	3	H	H	5	4-N	C	C	C	C	H	H	H	H
125	3	H	H	5	3-O	ls	C	C	C	H	H	H	Ac
126	3	H	H	5	3-O	ls	C	C	C	H	H	H	H
127	3	H	H	5	3-N	C	C	C	C	H	H	H	Ac
128	3	H	H	5	3-N	C	C	C	C	H	H	H	H
129	4	H	H	2	4-N	C	C	C	C	H	H	H	Ac
130	4	H	H	2	4-N	C	C	C	C	H	H	H	H
131	4	H	H	2	3-N	C	C	C	C	6-F	H	H	Ac
132	4	H	H	2	3-N	C	C	C	C	6-F	H	H	H
133	4	H	H	2	3-N	C	C	C	C	H	H	H	Ac
134	4	H	H	2	3-N	C	C	C	C	H	H	H	H
135	3	H	H	5	2-S	ls	C	C	C	H	H	H	Ac
136	3	H	H	5	2-S	ls	C	C	C	H	H	H	H
137	3	H	H	5	3-N	C	C	C	C		H	H	Ac
138	3	H	H	5	3-N	C	C	C	C		H	H	H
139	3	H	H	6	4-O	ls	N	C	C		H	-	Ac
140	3	H	H	6	4-O	ls	N	C	C		H	-	H
141	3	H	H	6	3-N	C	C	C	C		H	H	Ac
142	3	H	H	6	3-N	C	C	C	C		H	H	H
143	3	H	H	5	3-N	C	C	C	C		H	H	Ac
144	3	H	H	5	3-N	C	C	C	C		H	H	H
145	3	H	H	5	3-N	C	C	C	C	5-Cl	H	H	Ac
146	3	H	H	5	3-N	C	C	C	C	5-Cl	H	H	H
147	3	H	H	5	3-N	C	C	C	C	6-CN	H	H	Ac
148	3	H	H	5	3-N	C	C	C	C	6-CN	H	H	H
149	3	H	H	6	3-N	C	C	C	C	5-F	H	H	Ac
150	3	H	H	6	3-N	C	C	C	C	5-F	H	H	H
151	3	H	H	5	3-N	C	C	C	C		H	H	Ac
152	3	H	H	5	3-N	C	C	C	C		H	H	H
153	3	H	H	5	3-N	C	C	C	C	5-F	H	H	Ac
154	3	H	H	5	3-N	C	C	C	C	5-F	H	H	H
155	3	H	H	6	3-N	C	C	C	C		H	H	Ac
156	3	H	H	6	3-N	C	C	C	C		H	H	H
157	3	H	H	5	4-N	ls	N	C	C				Ac
158	3	H	H	5	4-N	ls	N	C	C				H
159	3	H	H	5	4-N	ls	N	C	C			H	Ac
160	3	H	H	5	4-N	ls	N	C	C			H	H
161	3	H	H	6	3-N	C	C	C	C	6-CN	H	H	Ac
162	3	H	H	6	3-N	C	C	C	C	6-CN	H	H	H
163	3	H	H	6	4-N	ls	N	C	C				Ac
164	3	H	H	6	4-N	ls	N	C	C				H
165	3	H	H	6	4-N	ls	N	C	C		H	H	Ac
166	3	H	H	6	4-N	ls	N	C	C		H	H	H
167	3	H	H	6	4-N	ls	N	C	C			H	Ac
168	3	H	H	6	4-N	ls	N	C	C			H	H
169	3	H	H	5	3-N	C	C	C	C	6-F	H	H	Ac
170	3	H	H	5	3-N	C	C	C	C	6-F	H	H	H
171	3	H	H	5	4-N	ls	N	C	C		H	H	Ac
172	3	H	H	5	4-N	ls	N	C	C		H	H	H
173	3	H	H	6	5-S	ls	C	N	C			-	Ac
174	3	H	H	6	5-S	Is	C	N	C			-	H
175	3	H	H	6	3-N	C	C	C	C		H	H	Ac
176	3	H	H	6	3-N	C	C	C	C		H	H	H
177	3	H	H	5	5-N	C	N	C	C	H	H	H	Ac
178	3	H	H	5	5-N	C	N	C	C	H	H	H	H
179	3	H	H	5	4-O	ls	N	C	C			-	Ac
180	3	H	H	5	4-O	ls	N	C	C			-	H
181	3	H	H	2	4-O	ls	N	C	C			-	Ac
182	3	H	H	2	4-O	ls	N	C	C			-	H
183	3	H	H	5	3-N	C	C	C	C	2-F	H	H	Ac
184	3	H	H	5	3-N	C	C	C	C	2-F	H	H	H
185	3	H	H	5	4-N	C	C	C	C	2-F	H	H	Ac
186	3	H	H	5	4-N	C	C	C	C	2-F	H	H	H
187	3	H	H	6	3-N	C	C	C	C	2-F	H	H	Ac
188	3	H	H	6	3-N	C	C	C	C	2-F	H	H	H
189	3	H	H	6	5-N	C	N	C	C	H	H	H	Ac
190	3	H	H	6	5-N	C	N	C	C	H	H	H	H
191	3	H	H	6	4-O	ls	N	C	C			-	Ac
192	3	H	H	6	4-O	ls	N	C	C			-	H
193	3	H	H	6	3-N	C	C	C	C	6-F	H	H	Ac
194	3	H	H	6	3-N	C	C	C	C	6-F	H	H	H
195	3	2-F	H	5	4-N	C	C	C	C	2-F	H	H	Ac
196	3	2-F	H	5	4-N	C	C	C	C	2-F	H	H	H
197	3	2-F	H	5	3-N	C	C	C	C	6-F	H	H	Ac
198	3	2-F	H	5	3-N	C	C	C	C	6-F	H	H	H
199	3	H	H	5	3-S	ls	C	C	C	H	H	H	Ac
200	3	H	H	5	3-S	ls	C	C	C	H	H	H	H
201	3	H	H	6	4-N	C	C	C	C	2-Cl	H	H	Ac
202	3	H	H	6	4-N	C	C	C	C	2-Cl	H	H	H
203	3	H	H	4	4-O	ls	N	C	C			-	Ac
204	3	H	H	4	4-O	ls	N	C	C			-	H
205	3		H	2	3-N	C	C	C	C	H	H	H	Ac
206	3		H	2	3-N	C	C	C	C	H	H	H	H
207	3		H	2	4-N	C	C	C	C	H	H	H	Ac
208	3		H	2	4-N	C	C	C	C	H	H	H	H
209	3	H	H	6	4-N	C	C	C	C	2-F	H	H	Ac
210	3	H	H	6	4-N	C	C	C	C	2-F	H	H	H
211	3	H	H	2	5-N	C	N	C	C	H	H	H	Ac
212	3	H	H	2	5-N	C	N	C	C	H	H	H	H
213	3	5-F	H	6	3-N	C	C	C	C	6-F	H	H	Ac
214	3	5-F	H	6	3-N	C	C	C	C	6-F	H	H	H
215	3	5-F	H	6	3-N	C	C	C	C		H	H	Ac
216	3	5-F	H	6	3-N	C	C	C	C		H	H	H
217	3	H	H	5	5-N	C	N	C	C		H	H	Ac
218	3	H	H	5	5-N	C	N	C	C		H	H	H
219	3	5-F	H	6	4-N	C	C	C	C		H	H	Ac
220	3	5-F	H	6	4-N	C	C	C	C		H	H	H
221	3	5-F	H	6	3-N	C	C	C	C		H	H	Ac
222	3	5-F	H	6	3-N	C	C	C	C		H	H	H
223	3	5-F	H	6	4-N	ls	N	C	C		H	H	Ac
224	3	5-F	H	6	4-N	ls	N	C	C		H	H	H
225	3	5-F	H	6	4-O	ls	N	C	C			-	Ac
226	3	5-F	H	6	4-O	ls	N	C	C			-	H
227	3	H	H	6	5-N	C	N	C	C		H	H	Ac
228	3	H	H	6	5-N	C	N	C	C		H	H	H
229	3	5-F	H	6	5-N	C	N	C	C	H	H	H	Ac
230	3	5-F	H	6	5-N	C	N	C	C	H	H	H	H
231	3	H	H	5	2-N	C	C	C	C	3-Cl	H	H	Ac
232	3	H	H	5	2-N	C	C	C	C	3-Cl	H	H	H
233	3	H	H	5	2-N	C	C	C	C		H	H	Ac
234	3	H	H	5	2-N	C	C	C	C		H	H	H
235	3	H	H	5	2-N	C	C	C	C		H	H	Ac
236	3	H	H	5	2-N	C	C	C	C		H	H	H
237	3	H	H	5	2-N	C	C	C	C		H	H	Ac
238	3	H	H	5	2-N	C	C	C	C		H	H	H
239	3		H	2	4-O	ls	N	C	C			-	H
240	3	H	H	2	3-N	C	C	C	C	6-F	H	H	H
241	4	H	H	2	4-O	ls	N	C	C			-	H
242	3	H	H	5	3-N	C	C	C	C		H	H	H
243	3	H	H	6	3-N	C	C	C	C		H	H	H
244	3	H	H	5	4-N	C	C	C	C		H	H	H
245	3	H	H	6	4-N	C	C	C	C		H	H	H
246	3	H	H	6	3-N	C	C	C	C	5-Cl	H	H	Ac
247	3	H	H	6	3-N	C	C	C	C	5-Cl	H	H	H
248	3	H	H	5	3-N	C	C	C	C		H	H	Ac
249	3	H	H	5	3-N	C	C	C	C		H	H	H
252	3	H	H	2	5-N	ls	N	N	N	H	-	-	Ac
253	3	H	H	2	5-N	ls	N	N	N	H	-	-	H
254	3	2-F	H	6	4-O	Is	N	C	C			-	Ac
255	3	2-F	H	6	4-O	ls	N	C	C			-	H
256	3	2-F	H	6	3-N	C	C	C	C	2-F	H	H	Ac
257	3	2-F	H	6	3-N	C	C	C	C	2-F	H	H	H
258	3	2-F	H	6	5-N	C	N	C	C	H	H	H	Ac
259	3	2-F	H	6	5-N	C	N	C	C	H	H	H	H
260	3	2-F	H	6	3-N	C	C	C	C	6-F	H	H	Ac
261	3	2-F	H	6	3-N	C	C	C	C	6-F	H	H	H
262	3	2-F	H	6	4-N	C	C	C	C	2-F	H	H	Ac
263	3	2-F	H	6	4-N	C	C	C	C	2-F	H	H	H
264	3	2-F	H	6	4-N	ls	N	C	C		H	H	Ac
265	3	2-F	H	6	4-N	ls	N	C	C		H	H	H
266	3	2-F	H	6	3-N	C	C	C	C		H	H	Ac
267	3	2-F	H	6	3-N	C	C	C	C		H	H	H
268	3	2-F	H	6	4-N	C	C	C	C		H	H	Ac
269	3	2-F	H	6	4-N	C	C	C	C		H	H	H
270	3	2-F	H	6	3-N	C	C	C	C	6-CN	H	H	Ac
271	3	2-F	H	6	3-N	C	C	C	C	6-CN	H	H	H
272	3	5-F	H	6	3-N	C	C	C	C	H	H	H	Ac
273	3	5-F	H	6	3-N	C	C	C	C	H	H	H	H
274	3	5-F	H	6	4-N	C	C	C	C	2-F	H	H	Ac
275	3	5-F	H	6	4-N	C	C	C	C	2-F	H	H	H
276	3	2-Cl	H	5	5-N	C	N	C	C	H	H	H	Ac
277	3	2-Cl	H	5	5-N	C	N	C	C	H	H	H	H
278	3	2-Cl	H	5	3-N	C	C	C	C	6-F	H	H	Ac
279	3	2-Cl	H	5	3-N	C	C	C	C	6-F	H	H	H
280	3	2-Cl	H	6	5-N	C	N	C	C	H	H	H	Ac
281	3	2-Cl	H	6	5-N	C	N	C	C	H	H	H	H
282	3	2-F	H	5	2-N	C	C	C	C	H	H	H	Ac
283	3	2-F	H	5	2-N	C	C	C	C	H	H	H	H
284	3	2-F	H	5	5-N	C	N	C	C	H	H	H	Ac
285	3	2-F	H	5	5-N	C	N	C	C	H	H	H	H

- What? In the table above: Pos-N indicates the position of the thioxyl group relative to the nitrogen atom in the pyridine cycle,Pos-A indicates the position of the heterocycle A relative to the nitrogen atom in the pyridine cycle,X indicates the nature of the primary heteroatom of the heterocycle A and its position relative to the bonding of the heterocycle A to the pyridine nucleus, ls means single bond,for substituents R1, R2 and R3, the figure indicates the position of the substituent on the heterocycle A relative to the heteroatom X. For the purposes of heading No 226, the compound is the compound with the formula: - What?

The antithrombotic activity of the compounds of the invention has been studied in vivo in rats by means of a test that reproduces venous thrombosis.

Venous thrombosis was induced according to the protocol described in Thromb. Haemost. 1992, 67(1), 176-179.

The test is performed on Wistar male rats, not on an empty stomach, weighing 250-280 g and divided into groups of 10 animals each. The test products are administered orally (tube) in solution or suspension in a 0.5% methylcellulose solution in water. The concentration of the compounds is calculated so that an amount of 10 ml/kg solution is absorbed orally. A thrombosis is induced at a time T after administration of the product and the formed thrombus is taken and weighed.The test was performed in accordance with the technique described by WESSLER (J. Applied Physiol. 1959, 943-946) using as the hypercoagulant a solution of activated factor X (Xa), supplied by Biogenic (Montpellier), at a dose of 7.5 nKat/kg. Venous stasis is performed exactly 10 seconds after the injection of the hypercoagulant. The activity of the test compounds was controlled at different doses after they were administered. The induction of thrombosis was made 2 hours after the administration of the compound.The concentration of the substance in the blood is the same as that observed in the presence of the compound of the invention, compared with the weight of the thrombus formed in the absence of the compound.

N° Exemple	Dose (mg/kg)	Temps (h)	Activité
22	6	2	100
24	6	2	96
30	6	2	97
40	6	2	96
108	6	2	95
122	6	2	93
130	6	2	91
140	6	2	96
142	6	2	97
224	6	2	99
226	6	2	97

These results show that the compounds of the invention exhibit good antithrombotic activity after oral administration.

The present invention therefore concerns a compound of formula (I) as defined in the invention and its salts with a pharmaceutically acceptable acid, solvates and hydrates for use as a medicinal product. The compound of formula (I) or a pharmaceutically acceptable salt, solvate or hydrate may be used in the preparation of an antithrombotic drug intended, in particular, for the treatment or prevention of venous or arterial circulation disorders, and in particular, to correct certain haematological parameters sensitive to the venous level, or to compensate for cardiac failure. The compounds of formula (I) or a pharmaceutically acceptable salt, solvate or hydrate may also be used in the preparation of a medicinal product intended for use after surgery or for the prevention of cardiovascular events such as stroke or coronary thrombosis or for the prevention of coronary artery disease, or for the prevention of coronary artery disease, or for the prevention of coronary artery disease.

The present invention therefore also relates to pharmaceutical formulations containing a compound of formula (I) or one of its pharmaceutically acceptable salts, solvates or hydrates. These pharmaceutical formulations generally contain suitable excipients. These excipients are selected according to the pharmaceutical form and the desired mode of administration, in particular oral or injectable.

These pharmaceutical formulations are prepared according to the conventional methods well known to the professional. e.g. the compounds of the invention may be formulated with physiologically acceptable excipients to obtain an injectable form for direct use, an injectable form for preparation in an extemporaneous manner or a solid form for oral administration such as a capsule or tablet.

As an example, an injectable form may be prepared preferably by freeze-drying of a filtered and sterilized solution containing the compound of the invention and a soluble excipient in sufficient quantity to obtain an isotonic solution after the addition of water for injection. The resulting solution may be administered either as a single subcutaneous or intramuscular injection or as a slow infusion. An oral form may be preferably presented as a capsule containing the compound of the invention finely ground or, better, micronized and mixed with excipients known to the trade, such as lactose, pre-glutamate and magnesium stearate.

In order to achieve the desired therapeutic or prophylactic effect, each unit dose may contain 10 to 500 mg of at least one compound of the invention.

Claims (16)

1. A thioxylose compound, characterized in that it is chosen from:

   a) the compounds of formula: in which:

   - the pentapyranosyl group represents a 5-thio-β-D-xylopyranosyl group,

   - R represents a hydrogen atom or a C₂-C₆ acyl group,

   - R' and R" each independently represent a hydrogen atom, a halogen atom, a C₁-C₄ alkyl group or a 6-fluoro-3-pyridinyl group,

   - A represents a 5- or 6-membered aromatic heterocycle of formula:

   in which:

   - X represents a nitrogen, oxygen or sulfur atom,

   - Y represents a carbon atom or a single bond,

   - Z₁, Z₂ and Z₃ each independently represent a carbon or nitrogen atom,

   - R₁, R₂ and R₃ each independently represent a hydrogen atom, a halogen atom, a cyano group, a C₁-C₄ alkyl group, a C₁-C₄ alkoxy group or a trifluoromethyl group; or

   - R₁ and R₂ form, together with the atoms of the heterocycle to which they are attached, an aromatic ring comprising 6 carbon atoms, A thus representing a fused bicyclic group,

   b) the addition salts of said compound.
2. The compound as claimed in claim 1, characterized in that A represents a benzofuranyl or a benzothienyl group.
3. The compound as claimed in claim 1 or 2, characterized in that the 5-thio-β-D-xylopyranosyl group is in the 3 position on the pyridine ring.
4. The compound as claimed in one of claims 1 to 3, characterized in that R' and R" each represent a hydrogen atom, a halogen atom or a methyl group.
5. The compound as claimed in one of claims 1 to 4, characterized in that A represents a pyridinyl ring.
6. The compound as claimed in one of claims 1 to 5, characterized in that R represents a hydrogen atom.
7. The compound as claimed in one of claims 1 to 6, characterized in that R represents a COCH₃ group.
8. A process for the manufacture of a compound as claimed in claim 1, characterized in that the following steps are carried out:

   a) reacting a pyridinol of formula: in which:

   - R' and R" each independently represent a hydrogen atom, a halogen atom or a C₁-C₄ alkyl group,

   - A represents a 5- or 6-membered aromatic ring of formula:

   in which:

   - X represents a nitrogen, oxygen or sulfur atom,

   - Y represents a carbon atom or a single bond,

   - Z₁, Z₂ and Z₃ each independently represent a carbon or nitrogen atom,

   - R₁, R₂ and R₃ each independently represent a hydrogen atom, a halogen atom, a cyano group, a C₁-C₄ alkyl group, a C₁-C₄ alkoxy group, or a trifluoromethyl group; or

   - R₁ and R₂ form, together with the atoms of the heterocycle to which they are attached, an aromatic ring comprising 6 carbon atoms, A thus representing a fused bicyclic group, with a 5-thioxylopyranose derivative of formula: in which Hal represents a halogen and R represents a C₂-C₆ acyl group, in an aprotic solvent, in the presence of a silver salt or of a zinc salt, in an anhydrous medium, at a temperature of between 25 and 110°C and for 1 to 10 hours, in order to obtain the compound of formula: in which A, R, R' and R" retain the same meanings as in the starting compounds;

   b) if necessary, reacting the compound of formula I obtained above with a solution of ammonia in methanol in order to bring about the deacylation and thus to replace the acyl group by hydrogen atoms and to obtain the compound of formula: in which R₁ and R₂ retain the same meanings as above;

   c) if necessary, reacting one of the compounds I or Ia obtained above with an acid according to methods known to a person skilled in the art in order to obtain the corresponding addition salt.
9. The process for the manufacture of a compound as claimed in claim 8, characterized in that stage (b) is brought about by the action of a metal alkoxide, in a catalytic amount in methanol, at a temperature of between 0 and 30°C and for 0.5 to 2 hours, in order to obtain the compound of formula Ia from the compound of formula I in which R represents a C₂-C₆ acyl group.
10. A process for the manufacture of a compound as claimed in claim 1, characterized in that the following steps are carried out:

    a) reacting the tetraacetylthioxylose of formula: in which Ac represents the acetyl group, with a compound of formula: in which:

    - R' and R" each independently represent a hydrogen atom, a halogen atom or a C₁-C₄ alkyl group,

    - A represents a 5- or 6-membered aromatic ring of formula:

    in which:

    - X represents a nitrogen, oxygen or sulfur atom,

    - Y represents a carbon atom or a single bond,

    - Z₁, Z₂ and Z₃ each independently represent a carbon or nitrogen atom,

    - R₁, R₂ and R₃ each independently represent a hydrogen atom, a halogen atom, a cyano group, a C₁-C₄ alkyl group, a C₁-C₄ alkoxy group or a trifluoromethyl group; or

    - R₁ and R₂ form, together with the atoms of the heterocycle to which they are attached, an aromatic ring comprising 6 carbon atoms, A thus representing a fused bicyclic group,

    in an aprotic solvent, in the presence of a catalyst of Lewis acid type, at a temperature of between 20 and 60°C and for 1 to 2 hours, in order to obtain the compound of formula: in which A, R, R' and R" retain the same meanings as in the starting compounds, b) if necessary, exchanging the acetyl groups with hydrogen atoms according to the methods applied in the preceding processes, in order to obtain the compound of formula Ia.
11. A process for the manufacture of a compound as claimed in claim 1, characterized in that the following steps are carried out:

    a) reacting a compound of formula: in which Hal is a halogen atom, R' and R" each independently represent a hydrogen atom, a halogen atom, other than bromine or iodine, or a C₁-C₄ alkyl group, and R represents a hydrogen atom or a C₂-C₆ acyl group; with a heteroarylboronic acid or an alkyl heteroarylboronate of formula: in which:

    - X represents a nitrogen, oxygen or sulfur atom,

    - Y represents a carbon atom or a single bond,

    - Z₁, Z₂ and Z₃ each independently represent a carbon or nitrogen atom,

    - R₁, R₂ and R₃ each independently represent a hydrogen atom, a halogen atom, preferably a fluorine atom, a cyano group, a C₁-C₄ alkyl group, a C₁-C₄ alkoxy group or a trifluoromethyl group; or

    - R₁ and R₂ form, together with the atoms of the heterocycle to which they are attached, an aromatic ring comprising 6 carbon atoms, A thus representing a fused bicyclic group,

    - Alk represents a hydrogen atom or a C₁-C₄ alkyl group;

    it being possible for the combination in addition to represent a "pinacolatoboryl" group, in the presence of a palladium catalyst, of a polar solvent and of cesium fluoride or sodium carbonate, at a temperature of between 70°C and 150°C for 5 minutes to 72 hours, in order to obtain the compound of formula: in which: R, R₁, R₂, R₃, R', R", X, Y, Z₁, Z₂ and Z₃ retain the same meanings as in the starting materials.
12. A process for the manufacture of a compound as claimed in claim 1, characterized in that the following steps are carried out:

    a) reacting a glycosylated pyridineboronic acid or a glycosylated pyridinylboronate of formula: in which R represents a hydrogen atom or a C₂-C₆ acyl group, R' and R" each independently represent a hydrogen atom, a halogen atom, other than bromine or iodine, or a C₁-C₄ alkyl group and Alk represents a hydrogen atom or a C₁-C₄ alkyl group, with a heteroaryl halide of formula: in which Hal represents a halogen and R₁, R₂ and R₃ each independently represent a hydrogen atom, a halogen atom, a cyano group, a C₁-C₄ alkyl group, a C₁-C₄ alkoxy group or a trifluoromethyl group; or R₁ and R₂ form, together with the atoms of the heterocycle to which they are attached, an aromatic ring comprising 6 carbon atoms, A thus representing a fused bicyclic group, in the presence of a palladium catalyst, of a polar protic solvent and cesium fluoride or sodium carbonate, at a temperature of between 70°C and 150°C for 5 minutes to 72 hours, in order to obtain the compound of formula: in which:

    R, R₁, R₂, R₃, R', R", X, Y, Z₁, Z₂ and Z₃ retain the same meanings as in the starting materials.
13. The compound as claimed in any one of claims 1 to 6 for its use as pharmacologically active substance.
14. The use of a compound as claimed in any one of claims 1 to 6 for the preparation of a medicament intended for the prevention or treatment of thrombosis or venous thrombosis.
15. The use of a compound as claimed in any one of claims 1 to 6 for the preparation of a medicament intended for the prevention or treatment of cardiac insufficiency.
16. The use of a compound as claimed in any one of claims 1 to 6 for the preparation of a medicament intended for the prevention of restenosis subsequent to an angioplasty or of pathologies of thromboembolic type.