Derivatives sulfonamida

 

(57) Abstract:

Usage: in medicine. The inventive product is derived sulfonamida . Reagent 1: derived sulfonic acid. Reagent 2: amino derivative.

The invention relates to new derivatives sulfonamida, method for their production and pharmaceutical compositions containing these compounds as the active ingredient.

Currently used for the treatment of cancer chemotherapeutic agents are substances of different nature, for example, alkylating agents such as cyclophosphamide; antimetabolites, such as methotrexate and fluorouracil inside the body; antibiotics, such as adriamycin, mitomycin and bleomycin; substances of vegetable origin, such as vincristine, and etopside, and metal complexes, such as cisplatin.

Derivatives of 4-aminobenzenesulfonamide (Japan patent N 3093/1968), derivatives of 2-sulfanilamide/finokalia (Japan patent N 426/1987), and derivatives m= AMSA [see I. Med. Chem 18, 1110 (1975)] is known as an active antitumor compounds having sulfonamidnuyu group.

Most of these compounds have low efficacy in the treatment of human cancers, Oswalt serious adverse reactions. In connection with the above, the development of new drugs with low toxicity and good antitumor activity, remains to the present time.

The aim of the present invention to provide new derivatives sulfonamida having excellent antitumor activity and low toxicity. Another objective of the present invention is to develop a method of producing such compounds, as well as the manufacture of pharmaceutical preparations containing these compounds as the active ingredient.

In the process of intensive research conducted by the authors of the present invention in order to obtain antitumor compounds with low toxicity, it was found that described below sulfonamidnuyu derivatives have excellent antitumor activity and low toxicity. And on the basis of this discovery, we developed the present invention.

Thus, the present invention relates to sulfonamidnuyu derivative of General formula (I) or their pharmacologically acceptable salts.

< / BR>
(I) where R1lower alkyl, lower alkoxy, amino;

R2
A N - Ilin-;

B represents a group of formula N - or where R5hydrogen, lower alkyl;

E represents a group of the formula

--R6where Q is oxygen or sulfur; R6hydrogen, lower alkoxy, lower alkylamino, 2-furyl, phenyl which may be substituted by lower alkyl, hydroxy, halogen, or R6pyridyl which may be substituted by lower alkyl, halogen;

E represents pyridyl, pyrimidinyl or phenyl which may be substituted by a lower alkyloxy, hydroxyl, lower alkyl, halogen, (lower) alkyloxy (lower) alkyloxy group, phenylcarbamoyloxy, phosphoryloxy, glucerna - siloxy, lower allyloxycarbonyl, dimethylaminocarbonylmethyl, aminoacetate, aminobenzoate, phenoxy; or farmacologicas acceptable salts; except when:

1. R1is lower alkyl, amino;

R2hydrogen; a and b of Gruppen-;

E is phenyl which may be substituted by hydroxyl, halogen, lower alkyloxy, lower alkyl, phenylcarbamoyloxy, lower allyloxycarbonyl, dimethylaminocarbonylmethyl, aminobenzoate;

2. R2lower alkyl, In kaidyn-;

E group of the formula

--R6where R6the lower alkyl, the alkyl is, halogen, phenylcarbamoyloxy, lower allyloxycarbonyl, dimetilaminoflavonola, aminobenzoate group, or their pharmacologically acceptable salts.

The lower alkyl groups represented by R1, R2, R5and R6and Deputy E [cm. formula (I)] are straight or branched alkyl groups having 1-6 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl (amyl), isopentyl, neopentyl, tert-pentyl, 1-methylbutyl, 2-methylbutyl, 1,2-dimethylpropyl, n-hexyl, isohexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 2.2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl. Among them, preferred are methyl, ethyl, propyl and isopropyl, and the most preferred are methyl and ethyl groups.

The lower alkoxy groups represented by R1, R3and R6are groups derived from the above alkyl groups, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy and t-butoxy group. Among A fluorine, chlorine and bromine.

Sulfonamidnuyu derivative represented by the above formula (I) may form a salt with acid or base. Salts of compounds (I) are also included in the scope of the present invention. Examples of such salts with inorganic acids are the hydrochloride, hydrobromide and sulfate, and organic acids acetate, lactate, succinate, fumarate, maleate, citrate, benzoate, methanesulfonate and n-toluensulfonate. Examples of basic salts are inorganic salts, such as salts of sodium, potassium and calcium; and organic salts such as triethylamine, arginine and lysine.

Needless to say, the hydrates of these compounds and their optical isomers when they exist, are also included in the scope of the present invention. Compounds of the present invention possess strong antitumor activity. Compounds of the present invention, which possess anti-tumor activity in the process of metabolism, for example, after oxidation, hydrolysis or conjugation in vivo, are also included in the scope of the present invention.

Compounds of the present invention of formula (I) can be obtained in various ways. Of these the most common are the following>
ais a hydrogen atom, a halogen atom, or a lower alkyl, lower alkoxy-protected hydroxyl, nitro, phenoxy, cyano, acetyl or protected amino group, is subjected to the reaction of interaction with the compound of General formula III

< / BR>
(III) where R2A , B and E are defined above, and Ra3and Ra4may be the same or different and represent a hydrogen atom or halogen atom, lower alkoxy or protected or protected amino group.

Reactive derivatives of sulfonic acids (II) are known, frequently used compounds such as sulfanilamide, sulfanilamide and N-sulfanilimide. Of these the most preferred is sulfonylated. The above reaction is carried out using stoichiometric equimolar amounts. Although this reaction can be used for virtually any solvent, however, it is desirable that the raw materials were soluble in these solvents, and these solvents did not come easily react with the source material. Such solvents are, for example, can be pyridine, tetrahydrofuran, dioxane, benzene, simple ether, methylene chloride, dimethyl is the as in the case of sulfanilamide, the reaction is preferably carried out in the presence of an appropriate acid binding agent. Therefore, the use of a basic solvent such as pyridine, is particularly preferable. If you use a neutral solvent, may be added to the basis, for example, such as a carbonate of an alkali metal or an organic tertiary amine. Needless to say that the solvents that can be used in the described reactions are not limited to the above examples. The reaction usually proceeds at room temperature, but if desired, can be carried out under cooling or heating. The reaction time usually ranges from 10 min to 20 h, and depends on the starting materials and the reaction temperature.

If the resulting sulfonamidnuyu derivative (I) aminohydrocinnamic or carboxyl group is protected, it can be unlocked in the normal way of removing the protective groups, for example, by treatment with acid, alkali treatment or catalytic reduction, if desired, to obtain the compound (I) having a free amino or carboxyl group.

(2) Connect edeleny above, and Eais an aromatic cyclic group with 6 members (which may contain 1 or 2 nitrogen atom in the ring), substituted by 1-3 substituents Ga, which may be the same or different and represent a halogen atom, a lower alkyl group, lower alkoxy group, hydroxyl group, carboxyl group which may be esterified or amidinophenoxy, lower alkylthio group, or phenoxy group, provided that at least one of Ga on the ring is a hydroxyl group, is subjected to reaction with a compound of General formula (V):

X-Y (V) where X is a group capable of binding an oxygen atom, a hydroxyl group, and Y is removed by the group, or with the anhydride of an inorganic acid or organic acid, which reacts with a hydroxyl group.

Connection X-Y represents a reactive derivative of aromatic and aliphatic acids, aromatic and aliphatic carboxylic acids, amino acids, which may be protected, phosphoric acid, which may be protected; sulfuric acid, which may be protected; carbamino acid, which may be substituted by a lower alkyl group; and saccharides,consultonline, o-chlorobenzylchloride, acetylchloride, N-(t-butoxycarbonylamino) imidazole, phosphorus oxychloride, chlorosulfonic acid, N,N-dimethylcarbamoyl, and 1,2,3,4-Tetra-o-acetyl-D-glucuronate. Examples of anhydrides are the anhydrides of inorganic acids, for example, by Diaspora and sulfur trioxide, as well as anhydrides of organic acids, for example, N-carboxyanhydride (NCA) -amino acid and the anhydride Stanovoy acid.

Although in the aforesaid reaction can be used for virtually any solvent, however, it is desirable that the raw materials were soluble in these solvents, and these solvents did not come easily react with the source material. Such solvents are, for example, pyridine, tetrahydrofuran, dioxane, benzene, simple ether, methylene chloride, dimethylformamide and a mixture of two or more of these solvents. If you are using a liquid source compounds such as phosphorus oxychloride, the reaction is carried out in the absence of solvent.

(3) the Compound of General formula (VI)

< / BR>
(VI) where Ra1, Ra3, Ra4A , B and E are defined above, is subjected to reaction with a compound of General formula

Ra2-L, where R

(4) the Compound of General formula (VII):

< / BR>
(VII) where Ra1, R2, Ra3, Ra4A and B defined above, is subjected to reaction with a compound of General formula (VIII):

R11-Z (VIII) where R11defined above, and Z is a carboxyl group or its reactive derivative, or, when R11is lower alkylamino group, (VII) reacts with the lowest alkylsulfonates.

Reactive derivatives of carboxylic acids used in the present invention, can be, for example, galodamadruga, acid anhydrides, active amide compounds and active esters.

Examples used golodnikov are the anhydrides and bromohydrin. Examples used acid anhydrides are mixed anhydrides monoalkylammonium acid, mixed acid anhydrides containing aliphatic carboxylic acids (such as acetic acid, pavlikova acid, valeric acid, isovalerianic acid, trichloroacetic acid), mixed anhydrides of carboxylic acids (such as benzoic acid) and symmetric anhydrides of the acids. Examples of active amide compounds, ispolzuemaya, the triazole, tetrazole and benzothiazole. Active esters chosen from the group consisting of methyl ester, methoxymethyl ether, cinematology ether, propargilovyh ether, 4-nitrophenyloctyl ether, 2,4-dinitrophenoxy ether, trichloranisole ether, 2,4-dinitrophenoxy ether, pentachlorphenol ether, metaliteracy ether, phenylazophenyl ether and esters with 1-hydroxy-1H-2-pyridone, N-hydroxysuccinimide, N-hydroxyphthalimide or 1-hydroxybenzotriazole.

Carboxylic acid (VIII) can interact with the amine (VII) in the presence of a condensing agent such as N,N'-dicyclohexylcarbodimide (DCC) or N-cyclohexyl-N'-morpholinobutyrophenone.

If R11is an amino group, a substituted lower alkyl group, an amine (VII) may react with the lowest alkylsulfonates. If R11is an amino group, an amine (VII) can react with alkali-metal salt of cyanic acid.

These reactions can be carried out in the presence of a base such as an organic tertiary amine (e.g. triethylamine, N,N-dimethylaniline or pyridine), a carbonate of an alkali metal, or a bicarbonate of an alkali metal or, if desired, acid. The reaction osushestvljali almost any solvents, however, it is desirable that the raw materials were soluble in these solvents, and these solvents did not come easily react with the source material. Such solvents are, for example, pyridine, tetrahydrofuran, dioxane, benzene, simple ether, methylene chloride, dimethylformamide and a mixture of two or more of these solvents. If you are using a reagent, it is difficult soluble in an organic solvent, such as cyanate, the reaction can be carried out in aqueous conditions. Solvents that can be used in the present invention are not limited to the above examples. The reaction temperature is also not critical. Usually used at room temperature, but if necessary, the reaction can be carried out with cooling or heating. The reaction time is from 5 minutes to 20 hours and depends on the starting compounds and the reaction temperature. If the product has a protected hydroxyl or amino group, it may be subjected to treatment to remove the protective groups, for example, acid treatment, alkaline treatment or catalytic recovery of obtaining the compound (I) having a free hydroxyl or amino-and nitro-groups using the standard method for example, catalytic reduction in the presence of a catalyst such as palladium carbon, or using zinc powder and hydrochloric acid.

Below is a description of the method of obtaining the original compound (IX) used in the present invention

< / BR>
(IX) where Ra3, Ra4A , B and E are defined above, or their salts.

The method of obtaining 1.

[chemical formula 20]

< / BR>
(IX) where L represents a halogen atom, and Ra3, Ra4A , B and E are defined above, R7-hydrogen.

Compounds of General formula (XII) can be synthesized by various methods described, for example, in the publications I. Med. Chem, 21, page 965, I. Org. Chem. 28, page 3 114, I. Chem. Soc. Perkin I, 1974, 1611, 1974, 1970 and 1979, 135, Helv. Chim. Acta, 61, page 2 452 or similar ways. That is, they can be obtained by reaction of compounds of General formula (X) with a compound of General formula (XI) in the absence or in the presence of an organic solvent, such as dimethylformamide, ethanol or dioxane, at room temperature or when heated.

If you want to remove the so formed galgenwaard, as a binder acids are added by organicsolvents, at least two equivalents of the compound (XI) to the equivalent of compound (X). If the product (XII) on its aromatic ring is a highly reactive halogen atom, can be carried out another reaction with alkoxide or an amine to turn in another connection. The compound of General formula (IX) can be obtained by recovering the compound (XII) obtained as described above is used to recover the nitro-groups. In a preferred variant of the process of recovery, catalytic reduction is carried out in the presence of a catalyst of palladium charcoal or using zinc powder and acetic acid. Catalytic reduction is usually carried out in an organic solvent, such as methanol, tetrahydrofuran or dimethylformamide, at atmospheric or increased pressure.

The method of obtaining 2

where Ra3, Ra4, R2, A, B, E and L are defined above.

Compounds represented by the General formula (IX) can be synthesized, for example, by the method described in I. Org Chem 24, page 1314, or I. Heterocycl. Chem, 20, s 1339, or a way similar to these methods. That is, they can be obtained by reaction of compounds of General Faure and sulfuric acid, in a solvent such as water, ethanol or diethylene glycol. To increase the speed of the reaction, the reaction mixture is preferably heated.

The method of obtaining 3.

where Ra3, Ra4, R7, A, B, E and a are defined above.

Compounds represented by formula (IX) can be synthesized, for example, by the method described in I. Chem Soc. (C) 1970, c. 1355 or a similar way. That is, they can be obtained by reaction of General formula (XIV) with a compound of General formula (XV) in the absence or presence of an organic solvent, such as dimethylformamide or dioxane, at room temperature or when heated.

The method of obtaining 4

where Ra3, Ra4, R7A , B and Ea defined above,

Eb represents F, defined above, in which at least one is a protected hydroxyl group.

Compounds represented by the General formula (XVII) can be obtained by reaction of compounds of General formula (XVI) with a compound of General formula: X-Y (V), where X and Y are defined above, or using the anhydride of an inorganic or organic acid that can react with a hydroxyl group. The reaction is positive inert solvent, which does not react with these compounds, such as dimethylformamide, tetrahydrofuran or dioxane. To increase the reaction rate to the reaction system may be added a base such as sodium hydride, potassium carbonate or triethylamine, or may be increased reaction temperature. If R7is a hydrogen atom, before the reaction c X-Y (V) it is sometimes desirable to protect its standard amino-protecting group, such as benzyloxycarbonyl group, and after completion of the reaction, the protective group can be removed. Compounds represented by the General formula (XVIII) can be obtained by the reduction of compounds (XVII) obtained in accordance with the above method of restoring the nitro-groups.

The method of obtaining 5

< / BR>
(VII) where Ra1, R2, Ra3, Ra4A , B and L are defined above.

Compounds represented by the General formula (VII) can be obtained by restoring the compounds of General formula (XIX) with the use of compounds of General formula (XX). The reaction conditions depend on the used compounds. Preferably, to 1 equivalent of sulfanilamide (XIX) use 2-4 equivocal, pyridine, dimethylformamide or similar Reaction can also be carried out in aqueous conditions. Usually, the reaction is carried out at room temperature, but if necessary, it can be carried out under cooling or under heating.

If the compounds of the present invention are used as medicines, they can be administered orally or parentline. Enter the dose varies depending on symptoms, age, sex, weight and sensitivity of the patient; the method of administration, time and interval of administration; the properties, composition and type of the drug; and the form of the active ingredient.

This dose is usually from 10 to 6000 mg, preferably of about 50-4000 mg, and most preferably 100-3000 mg per day for an adult. This dose can be entered by parts 1 to 3 times a day.

When getting a solid preparation for oral administration, the active ingredient may be added a filler and, if necessary, a binder, disintegrator, lubricant, coloring agent, modifier, etc. when this specified product can be manufactured in the form of tablets, coated tablets; granules; granules, powder or capsules.

cellulose and silicon dioxide. Examples of the binder are polyvinyl alcohol, polyvinyl ether, ethylcellulose, methylcellulose, acacia, tragakant, gelatin, shellac, hydroxypropylcellulose, hypromellose, calcium citrate, dextrin and pectin. Examples of sizing are magnesium stearate, talc, polyethylene glycol, krasnozem and hardened vegetable oils. The drugs can also be added coloring agents. Examples of modifiers are cocoa powder, methanol, aromatic powders, essential oil of peppermint, camphor and ground cinnamon. These tablets and granules may be coated with sugar, gelatin, etc.

When getting drugs for injection, the active ingredient may be added as a pH modifier, buffer, suspendisse agent, solubilizer, stabilizer, isotonic agent, a preservative, etc. when this specified product can be manufactured in the form of a form for intravenous, subcutaneous or intramuscular injection. If necessary, these drugs can be liofilizovane.

Examples suspendida agents include methylcellulose, Polysorbate 80, hydroxyethylcellulose, acacia, powdered tragakant, natriciteres carboxymethylcellulose and the e castor oil, Polysorbate 80, nicotinamide, polyoxyethylenesorbitan, macrogel and ethyl esters of fatty acids of castor oil.

Examples of the stabilizer include sodium sulfite, metasulfite sodium and simple ether. Examples of preservatives are methyl n-hydroxybenzoate, ethyl n-hydroxybenzoate, sorbic acid, phenol, cresol and chlorocresol.

The implementation of the present invention.

Experimental example 1.

In vitro antitumor test KV-cells (cells from nacogdoche human):

1,25 x 103(0.1 ml) KV-cells suspended in the medium RPM1 1640 (product of Nissui Seiyaku Co. Ltd.) containing 20% amniotic calf serum, penicillin (100 u/ml), streptomycin (100 μg/ml), mercaptoethanol (5 x 10-5M) and sodium pyruvate (1 mm), were placed in each well of 96-well plates to micrometrology, and cultured in an incubator containing 5% carbon dioxide for 1 day at 37aboutC.

The compound of the present invention was dissolved in dimethyl sulfoxide and received 20 mg/ml solution, which was diluted to a concentration of 100 μg/ml of culture fluid containing 0.1% amniotic calf serum in the medium RPM1 1640. This concentration was maksymalny calf, containing dimethyl sulfoxide. This solution was added to the KV-cells in each well with the above-described culture in an amount of 0.1 ml, and cultured in an incubator containing 5% silicon dioxide, for 3 days at 37aboutC.

After completion of the culturing, each well was added 0.05 ml MTT(3-(465-dimethylthiazol-2-yl)-2,5-definite-razole bromide) solution (3.3 mg/ml), and cultured for another 1 h and Then from each well was removed supernatant by suction, and the resulting thus formazan was dissolved in 0.1 ml of dimethylsulfoxide. Then was determined by optical density at 540 nm using a reader device, using as indicator the number of viable cells. The percentage of inhibition was calculated by the formula below, and then determined the concentration of the test compound required for 50% inhibition (IC50).

[Numerical formula 1]

The percentage of inhibition (%) (s-T)/C x 100

T of the optical absorption wells containing compound,

With the optical absorption wells containing no test compound,

IC50the values determined in this way are presented in table. 2.

Comparative connections lead 38 (colorectal cancer mouse):

About 75 mg of the rectum 38 subcutaneously transplanted from a lateral side of each mouse BDF1(female, 7 weeks). The compound of the present invention suspended in 0.5% methylcellulose and administered orally once a day, starting from the next day and continuing for 8 days. The control group consisted of 10 mice and the test group consisted of 6 mice.

21 days after the transplantation, the tumor was excised and weighed. The degree of inhibition of tumor growth of the test group relative to the control group was determined by the following formula:

[Numerical formula 2]

The degree of inhibition of tumor growth (%) (s-T)/C x 100

T the average weight of the tumors in the group of mice that were administered the test compound,

With the average weight of tumors in the control group.

The results of the experiments are presented in table. 3.

Experimental example 3: Test for toxicity.

Groups of 5 mice BDF1(female, 7 weeks) was administered once a 0.5% suspension of the compound of example 3, 4 or 6 in methylcellulose, and within 7 days after the introduction watched the viability of the treated mice. No mouse died even with the introduction of 1651 mg/kg connection.

As can be seen from puhachevym action. In addition, the compounds of the present invention are highly harmless drug and therefore can be successfully used for the treatment of malignant tumors, i.e., as antitumor agents.

P R I m e R s.

Examples of obtaining illustrate how to obtain the source compounds for the synthesis of compounds of the present invention, the following examples illustrate typical compounds of the present invention, but these examples should not be construed as some limitations of the possible embodiments of the present invention.

An example of obtaining 1.

2-Aniline-3-nitropyridine:

[chemical formula 25]

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The mixture 11,21 g (70 mm) 2-chloro-3-nitropyridine and 19,56 g (210 mm) of aniline was heated, with stirring, at 100aboutC for 1 h, the Reaction mixture was cooled to room temperature and dissolved in ethyl acetate. The solution was washed with an aqueous solution of citric acid and then with water. After drying with magnesium sulfate, the solvent is kept under reduced pressure, and the residue was recrystallized from a mixture of ethyl acetate and n-hexane, resulting in received 13,7 target compound.: at 6.84 (1H, DD, j=8,4, 4,4 Hz), 7.18 in-7,22 (1H, m); 7,37-the 7.43 (2H, m), 7,62-to 7.68 (2H, m), 8,49 (1H, DD, j=4,4, 2.0 Hz), 8,53 (1H, DD, j=8,4, 2.0 Hz), 10,12 (1H, Shir. C)

Elemental analysis for C11H9N3O2:

Calculated: 61,39; N 4,22; N19,53

Found: C 61,49; H 4,34; N 19,23

Example of receipt 2.

3-Amino-2-anilinopiperidine

[chemical formula 26]

< / BR>
6.8 g (31,6 mm) of the compound obtained in the example of obtaining 1, was dissolved in a mixture of 40 ml of tetrahydrofuran and 6 ml of methanol. Then to the solution was added palladium charcoal in order to implement the hydrogenation at room temperature and atmospheric pressure. Then palladium angle drove by filtration under reduced pressure, and the residue was precrystallization from a mixture of ethyl acetate and n-hexane, which was obtained 5.5 g of the target compound.

So pl. 143-144aboutWITH

FAB mass spectroscopy (FAB-MS (m/z):186 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 4,95-5,10 (2N, W), is 6.61 (1H, DD, j=7,2, 4,8 Hz), 6,80-6,86 (1H, m), 6.90 to (1H, DD, j=7,2, 1,6 Hz), 7.18 in-7,24 (2H, m), 7,49 (1H, DD, j=4,8, and 1.6 Hz), 7,60-the 7.65 (2H, m); of 7.69 (1H, s).

Elemental analysis for C11H11N3:

Calculated: C 71,33; H of 5.99; N 22,69

Found: C 71,49; H 6,04; N 22,59

Example for the preparation of 3.

4-[(3-Nitro-2-pyridyl)amino]phenol

[x is of dimethylformamide, and the resulting mixture was stirred 40 min at 100aboutC. the Solvent is kept under reduced pressure and treated in the manner described in example get 1, after which the product was recrystallized from ethanol and obtained 9.4 g of the target compound.

So pl. 143-144aboutWITH

FAB-MS (m/z): 231 (M+)

1H-NMR (CDCl3) (ppm): 5,23 (1H, s); 6,79 (1H, DD, j=4,8, and 8.4 Hz), at 6.84 (2H, d, j= 8,8 Hz), 7,41 (2H, d, j=8,8 Hz), 8,44 (1H, DD, I=1,6, 4,8 Hz), charged 8.52 (1H, DD, I=1,6, and 8.4 Hz), 9,94 (1H, Shir. C).

Elemental analysis for C11H9N3O3:

Calculated: C 57,14; H to 3.92; N 18,18

Found: C 57,15; H of 3.97; N 18,14

Example 4.

4-[(3-Amino-2-pyridyl)amino]phenol

[chemical formula 28]

HO

a 9.25 g (40 mm) of the compound obtained in the example of a 3, catalytically recovered and treated in a manner analogous to the one described in example getting 2, after which the product was recrystallized from methanol and was received with 7.8 g of the target compound.

So pl. 205-207aboutWITH

FAB-MS (m/z): 202 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 4,94 (2H, Shir. C); 6,50 (1H, DD, j=4,8 and 7.6 Hz); 6,66 (2H, d, j=8,8 Hz); PC 6.82 (1H, DD, j=1,6 and 7.6 Hz); 7,38 (1H, s); 7,39 (2H, d, j=8,8 Hz); 7,40 (1H, DD, I=1,6, 4,8 Hz), cent to 8.85 (1H, s).

Elemental analysis for C11H11NRho-2-pyridyl)amino]phenol

[chemical formula 29]

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So pl. 148-149aboutC (recrystallized from ethanol)

FAB-MS (m/z): 232 ([M+H]+)

1H-NMR (CDCl3) (ppm): 5,31 (1H, Shir. C); of 6.65 (1H, DD, j=8.0 a, 2,4 Hz), 6,85 (1H, DD, j=8,4, 4,8 Hz), was 7.08 (1H, DD, j=8.0 a, 2,4 Hz), 7,24 (1H, t, j= 8.0 Hz), 7,37 (1H, t, j=2.4 Hz), 8,49 (1H, DD, j=4,8, and 1.6 Hz), 8,54 (1H, DD, j=8,4, and 1.6 Hz), 10,11 (1H, Shir. C).

Elemental analysis for C11H9N3O3:

Calculated: 57,14; H to 3.92; N 18,17

Found: C 57,33; H is 4.03; N 18,18

Example of getting a 6.

3-[(3-Amino-2-pyridyl)amino]phenol

[chemical formula 30]

< / BR>
So pl. gradual decomposition is observed at 198aboutC (after recrystallization from ethanol);

FAB-MS (m/z): 202 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 5,04 (2H, s); 6,24-6,28 (1H, m); 6,60 (1H, DD, j= 7,6, 4,8 Hz), 6.89 in (1H, DD, j=7,6, and 1.6 Hz), 6,97-6,99 (2H, m); 7.23 percent (1H, Shir. C) to 7.50 (1H, DD, j=4,8, and 1.6 Hz); EUR 7.57 (1H, s); 9,10 (1H, s).

Elemental analysis for C11H11N3O:

Calculated: C 65,66; H 5,51; N TO 20.88

Found: C 65,92; H 5,58; N 20,86

Example of getting a 7.

2-[(4-Methoxyethoxymethyl)amino]-3-nitropyridine

[chemical formula 31]

CH3OCH2O

8,4 g (54,8 mm) 4-ethoxymethyleneamino and 7.5 g (49 mm) 2-chloro-3-nitropyridine was dissolved in 35 ml of dimethylformamide. After that, the races who, the ri 100aboutC for 4 h and Then the reaction liquid was cooled to room temperature, and nerastvorimaya substance thus formed was removed by filtration. The solvent is kept under reduced pressure, and the residue was dissolved in ethyl acetate. The solution was washed with an aqueous solution of citric acid and then with water. After drying with magnesium sulfate, the solvent is kept under reduced pressure, and the residue was recrystallized from ethanol, resulting in a received target connection.

So pl. 80-81aboutWITH

FAB-MS (m/z): 275 (M+)

1H-NMR (CDCl3) (ppm): 3,50 (3H, c); 5,19 (2H, s); 6,79 (1H, DD, j=4,4, 8,4 Hz); was 7.08 (2H, d, j=8,8 Hz); 7,50 (2H, d, j=8,8 Hz); to 8.45 (1H, DD, I= 1,6; and 4.4 Hz); 8,51 (1H, DD, I=1,6, and 8.4 Hz), 9,99 (1H, Shir. C).

Elemental analysis for C13H13N3O4:

Calculated: C 56,73; H 4,76; M 15,27

Found: C 57,06; H a 4.83; N 15,02

Example obtain 8

2-[N-benzyloxycarbonyl-N-(4-methox - Metrocity)-amino]-3-nitropyridine

[chemical formula 32]

CH3OCH2O

4.0 g (14.5 mm) of the compound obtained in the example of a 7, was dissolved in 70 ml of dimethylformamide. Then to the solution was added 720 g (18 mm) of 60% sodium hydride. And stirring at room temperature, the solution to the solvent drove away under reduced pressure. Then to the residue was added ethyl acetate and water, and the ethyl acetate layer was separated. The selected layer was washed with water and then was dried, concentrated, and was purified by column chromatography on silica gel, which was obtained 4.5 g of oily target compound.

1H-NMR (CDCl3) (ppm): 3,47 (3H, s); of 5.17 (4H, s+C); 7,06 (2H, d, j=8,8 Hz); 7,22-7,26 (2H, m); 7,29-7,33 (4H, m); 7,37 (2H, d, j=8,8 Hz); 8,29 (1H, d, j=8.0 Hz); 8,56 (1H, d, j=4.4 Hz).

Example of receipt 9.

4-[N-benzyloxycarbonyl-N-(3-nitro-2-pyridyl)amino]phenol

[chemical formula 33]

HO

500 mg (1,22 mm) of the compound obtained in the example of obtaining 8, was dissolved in a mixture of 6 ml of tetrahydrofuran and 1 ml of water. To the resulting solution were added 2 ml conc. of hydrochloric acid. After the mixture is stirred over night at room temperature and the solvent is kept at reduced pressure. To the residue was added ethyl acetate and saturated aqueous sodium bicarbonate solution, and formed thus the ethyl acetate layer was separated. The selected layer was washed with water (drained magnesium sulfate) and concentrated, resulting in a received 445 mg of the target compound.

1H-NMR (DMCO-d6) (ppm): 5,11 (2H, c); 6,77 (2H, d, j=8,8 Hz); 7.18 in-7,24 (4H, m); 7,31-7,34 (3H, m); 7,58 3-Amino-2-pyridyl)amino]phenyl] tert-butoxy-carbonyl-aminoacetate

[chemical formula 34]

(CH3)3COCONHCH2COO

440 mg (1.2 mm) of the compound obtained in the example of a 9, 250 mg (1,43 mm) of N-(tert-butoxycarbonyl)-glycine and 25 g (0.2 mm) 4-dimethylaminopyridine was dissolved in 10 ml of pyridine. 290 mg (1,41 mm) of 1,3-dicyclohexylcarbodiimide was added to the obtained solution. After stirring overnight at room temperature, the solvent is kept at reduced pressure. To the residue was added ethyl acetate, undissolved matter was removed by filtration, and the solvent is kept at reduced pressure. The residue was purified by column chromatography on silica gel, and the compound obtained catalytically was restored in the presence of palladium charcoal in a standard way. Then the catalyst was removed followed by concentration and the residue was purified by column chromatography on silica gel, resulting in a received 236 mg of the target compound.

1H-NMR (DMCO-d6) (ppm): of 1.41 (9H, c); 3,93 (2H, d, j=6.0 Hz); of 5.05 (2H, Shir. C); 6,62 (1H, DD, j=4,8, 7,2 Hz); 6.90 to (1H, DD, I=1,6, 7,2 Hz); of 6.96 (2H, d, j=9,2 Hz); 7,37 (1H, Shir. t, j=6.4 Hz); 7,49 (1H, DD, I=1,6, 4,8 Hz); to 7.64 (2H, d, j=9,2 Hz), 7,79 (1H, s).

An example of obtaining 11. 4-[[3-(4-Methoxybenzenesulfonamide)-2-pyridyl] amino]phenyl-2,3,4,6-tetramer 6, and 3,959 g (10,14 mm) -D-glucose pentaacetate suspended in 200 ml of 1,2-dichloroethane. To the resulting suspension, with stirring and cooling with ice in a nitrogen atmosphere, one drop was added 30 ml of a 1.0 M solution of tin tetrachloride in dichloromethane. After stirring for 2 hours under ice cooling, and then for 4 days at room temperature, the reaction mixture was added to ice water containing 16 g of sodium bicarbonate. Organic solvent drove away under reduced pressure. To the residue was added ethyl acetate, and formed nerastvorimaya substance was removed by filtration. The ethyl acetate layer was separated, washed with water, dried, concentrated and was purified by column chromatography on silica gel, resulting in a received 2,47 g of target compound.

1H-NMR (CDCl3) (ppm): 2,04 (3H, s), is 2.05 (3H, s); of 2.08 (3H, s); 2,10 (3H, s); is 3.08-3,86 (1H, m); a-3.84 (3H, s); 4,17 (1H, DD, j=12,4, 2,4 Hz); 4,30 (1H, DD, j=12,4, 5,6 Hz); 4,99 (1H, d, j=7,6 Hz); 5,16 (1H, t, j=9.6 Hz); 5,23-5,32 (2H, m); 6,37 (1H, Shir. C); is 6.54 (1H, DD, j=4,8 and 7.6 Hz); at 6.84 (1H, DD, j= 1,6 and 7.6 Hz); 6,92 (2H, d, j=8,8 Hz); 6,94 (2H, d, j=8,8 Hz); to 7.32 (1H, Shir. C); 7,38 (2H, d, j=8,8 Hz); of 7.69 (2H, d, j=8,8 Hz); 8,07 (1H, DD, I=1,6, 4,8 Hz).

Example 12.

N-(2-AMINOPHENYL)-4-methoxybenzyl - honami

[chemical formula 36]

< / BR>

So pl. 141-142aboutC (after recrystallization from ethanol);

FAB-MS (m/z): 279 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 3,81 (3H, s); 4,91 (2H, Shir. C); 6,37 (1H, dt, I= 1,6, 7,2, 8.0 Hz); 6,60 (1H, DD, I=1,6, 8.0 Hz); 6,66 (1H, DD, I=1,6, 8.0 Hz), 6,86 (1H, dt, I=1,6, 7,2, 8.0 HZ), 7,03 (2H, d, j=8,8 Hz), to 7.61 (2H, d, j=8,8 Hz), 9,07 (1H, Shir. C).

Elemental analysis for C13H14N2O3S:

Calculated: C 56,10; H 5,07; N 10,07

Found: C 55,98; H to 5.03; N 10,00

Example of getting a 13.

N-(2-AMINOPHENYL)-4-nitrobenzoyl-foamed:

[chemical formula 37]

< / BR>
The target compound was obtained in a manner analogous to the method in example 12.

So pl. 190-191aboutC (recrystallized from benzene)

FAB-MS (m/z): 294 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 4,90 (2H, Shir. C); 6.42 per (1H, dt, I=1,6, 8.0 Hz); is 6.61 (1H, DD, I=1,6, 8.0 Hz); of 6.71 (1H, DD, I=1,6, 8.0 Hz); 6,91 (1H, dt, I=1,6, 8.0 Hz); to $ 7.91 (2H, d, I 49,14; H OF 3.78; N 14,33

Found: 49, 38; H 3,82; N 14,13

Example of getting a 14.

N-(2-amino-3-were)-4-methoxy-benzosulfimide

[chemical formula 38]

< / BR>
The target compound was obtained in a manner analogous to the method described in example 12.

So pl. 177-178aboutC (recrystallized from ethanol)

FAB-MS (m/z):293 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 2,03 (3H, s); 3,81 (3H, s); and 4.75 (2H, Shir. C); 6,30 (1H, t, j=7,6 Hz); 6,44 (1H, DD, j=1,2, 7,6 Hz); 6,79 (1H, DD, j=1,2, 7,6 Hz);? 7.04 baby mortality (2H, d, j=8,8 Hz); to 7.61 (2H, d, j=8,8 Hz).

Elemental analysis for C14H16N2O3S:

Calculated: C 57,52; H 5,52; N 9,58

Found: C 57,76; H 5,51; N TO 9.57

P R I m e R 1.

N-(2-aniline-3-pyridyl)-n-tawassul - foamed

[chemical formula 39]

< / BR>
3.7 g (20 mm) of the compound obtained in example getting 2, was dissolved in 30 ml of pyridine. To this solution, stirring at room temperature, the parts were added 30 ml 3,81 g (20 mm) of n-toluensulfonate in tetrahydro - furan. After stirring overnight, the solution is kept under reduced pressure, and the residue was dissolved in ethyl acetate. The solution was washed with water and dried with magnesium sulfate. The solvent is kept under reduced pressure, the residue p is m/z): 340 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): of 2.23 (3H, s); of 6.73 (1H, DD, j=4,8 and 7.6 Hz); 6,86-6,92 (1H, m); 7.18 in-7,24 (2H, m); from 7.24 (2H, d, j=8.0 Hz); 7,27 (1H, DD, j= 7,6, and 1.6 Hz); of 7.36-7,42 (2H, m); rate of 7.54 (2H, d, j=8.0 Hz); 7,86 (1H, s); to 7.99 (1H, DD, j=4,8, and 1.6 Hz); 9,62 (1H, s).

Elemental analysis for C18H17N3O2S:

Calculated: 63,70; H of 5.05; N 12,38

Found: C 63,77; H 5,11; N TO 12.28

P R I m m e R 2.

N-(2-aniline-3-pyridyl)-4-ethylbenzophenone

[chemical formula 40]

< / BR>
3.11 g (16,8 mm) of the compound obtained in example getting 2, was subjected to the reaction of interaction of 3.43 g (16,8 mm) of n-ethylbenzaldehyde and the product was treated in the manner described in example 1, resulting in a received 0.5 g of the target compound.

So pl. 138-139aboutC (after recrystallization from ethanol)

FAB-MS (m/z): 354 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): of 1.02 (3H, t); 2,50 (2H, square); 6,72 (1H, DD, j= 5,2, 8.0 Hz); 6,83-6,89 (1H, m); 7,14-7,20 (2H, m); from 7.24 (2H, d, j=8,4 Hz); 7.29 trend (1H, DD, j= 8,0, 1.8 Hz); 7,32-7,37 (2H, m); rate of 7.54 (2H, d, j=8,4 Hz); 7,80 (1H, s); of 7.97 (1H, DD, j=5,2, 1.8 Hz); a 9.60 (1H, s).

Elemental analysis for C19H19N3O2S:

Calculated: C 64,57; H 5,42; N 11,89

Found: C 64,89; H 5,33; N 12,00

P R I m e R 3.

N-(2-aniline-3-pyridyl)-4-methoxime - solarpanel

[chemical formula is of cybersolutionindia and the obtained product was treated by the method described in example 1, which was obtained 2.6 g of the target compound.

So pl. 172-173aboutC (after recrystallization from ethanol)

FAB-MS (m/z): 356 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 3,68 (3H, s); of 6.71 (1H, DD, j=7,6, 5.0 Hz); 6,84-of 6.90 (1H, m), 6,92 (2H, d, j=9,2 Hz); 7,15-7,22 (2H, m); of 7.25 (1H, DD, j= 7,6, 1.2 Hz); of 7.36-7,42 (2H, m); EUR 7.57 (2H, d, j=9,2 Hz); 7,86 (1H, s); of 7.97 (1H, DD, j=5.0 and 1.2 Hz); 9,51 (1H, s).

Elemental analysis for C18H17N3O3S:

Calculated: C 60,83; H 4,82; N 11,82

Found: C 61,02; H 4,69; N UP 11,86

P R I m e R 4. 4-Methoxy-N-[2-[(4-methoxyphenyl)AMI-but]-3-pyridyl]benzene-sulfonamide

[chemical formula 42]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 145-147aboutC (after recrystallization from ethanol)

FAB-MS (m/z): 386 ([M+H]+)

1H-NMR (CDCl3) (ppm): with 3.79 (3H, s); of 3.85 (3H, s); 6,16 (1H, Shir. C); of 6.52 (1H, DD, j= 4,8 and 7.6 Hz); 6,85 (3H, d, j=8,8 Hz); 6,93 (2H, d, j=8,8 Hz); for 7.12 (1H, Shir. with); to 7.32 (2H, d, j=8,8 Hz); of 7.69 (2H, d, j=8,8 Hz); 8,07 (1H, DD, I=1,6, 4,8 Hz).

Elemental analysis for C19H19N3O4S:

Calculated: C 59,21; H equal to 4.97; N 10,90

Found: C 59,26; H of 5.05; N 10,75

P R I m e R 5.

4-Methoxy-N-[2-[(4-methoxyethoxide - nil)amino] -3-pyridyl] benzosulfimide

[chemical formula 43]after recrystallization from ethanol)

FAB-MS (m/z): 416 ([M+H]+)

1H-NMR (CDCl3) (ppm): 3,48 (3H, s); a 3.83 (3H, s); 5,13 (2H, s); 6,45 (1H, Shir. C); of 6.52 (1H, DD, j=4,4, 7,6 Hz); 6.87 in (1H, DD, j=1,6 and 7.6 Hz); 6,92 (2H, d, j=8,8 Hz); 6,97 (2H, d, j=8,8 Hz); 7,16 (1H, Shir.c); 7,31 (2H, d, 8,8 Hz); of 7.69 (2H, d, j=8,8 Hz); 8,07 (1H, d).

Elemental analysis for C20H21N3O5S:

Calculated: C 57,82; H 5,09; N 10,11

Found: C 57,93; H 5,02; N 9,84

P R I m e R 6. N-[2-[(4-hydroxyphenyl)amino]-3-Piri-DIL]-4-methoxybenzenesulfonamide

[chemical formula 44]

< / BR>
1.01 g (5 mm) of the compound obtained in example 4, was subjected to the reaction of 1.05 g (5 mm) of n-methoxybenzenesulfonamide, and the resulting product was treated in a manner similar to that described in example 1, resulting in a received target connection.

So pl. 178-179aboutC (after recrystallization from ethanol)

FAB-MS (m/z): 372 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 3,75 (3H, s); 6,60 (1H, DD, j=4,8 and 7.6 Hz); 6,63 (2H, d, j=8,8 Hz); 6,98 (2H, d, j=8,8 Hz); 7,14 (2H, d, j=8,8 Hz); 7.18 in (1H, DD, j= 1,6 and 7.6 Hz); 7,58 (1H, Shir. C); of 7.60 (2H, d, j=8,8 Hz); 7,88 (1H, DD, I=1,6, 4,8 Hz); 8,97 (1H, s); 9,44 (1H, s).

Elemental analysis for C18H17N3O4S:

Calculated: C 58,21; H br4.61; N 11,31

Found: C 58,40; H of 4.67; N 11,38

2.0 g of target compound was dissolved in 50 ml of tetrahydrofuran. recristallization of methanol, and was obtained 1.9 g of the hydrochloride of the target compounds.

So pl. gradual decomposition was observed at 225aboutC.

Elemental analysis for C18H17N3O4S x xHCl

Calculated: C 53,01; H of 4.45; N, 10.30 A.M.

Found: C 52,97; H 4,33; N 10,19

P R I m e R 7.

4-Methoxy-N-[2-[(4-pyridyl)amino]-3 - pyridyl]benzosulfimide

[chemical formula 45]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 172-173aboutC (after recrystallization from ethyl acetate)

FAB-MS (m/z): 357 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): to 3.67 (3H, s); 6,86-6,91 (3H, m); 7,37 (1H, DD, j= 1,6 and 7.6 Hz); of 7.48 (2H, d, j=5.6 Hz); rate of 7.54 (2H, d, j=9,2 Hz); 8,04 (1H, DD, I=1,6, 4,8 Hz); compared to 8.26 (2H, d, j=5.6 Hz); 8,59 (1H, Shir. C).

Elemental analysis for C17H16N4O3S:

Calculated: C 57,29; H a 4.53; N 15,72

Found: 57,37; H 4,56; N 15,66

P R I m e R 8.

4-Methoxy-N-[2-[(4-were)amino]-3-pyridyl]benzene-sulfonamide

[chemical formula 46]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 188-189aboutC (after recrystallization from ethanol)

FAB-MS (m/z): 370 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): of 2.21 (3H, s); of 3.69 (3H, s); 6,66 (1H, DD, j= 6,4, 2,4 Hz); 6,92 (2H, d, j=7.2 Hz); 6,99 (2H, d, j=7,6 Hz); 7,21 (1H, DD, j= 6,4, and 1.6 Hz); 7,27 (2H, d, j=7.2 Hz); 7,56 (2H, d, j=7, 3
S:

Calculated: C 61,77; H 5,18; N 11,38

Found: C 61,82; H to 5.21; N 11,30

P R I m e R 9. N-[2-[(2-forforever)amino]-3-PI-rider]-4-methoxybenzenesulfonamide

[chemical formula 47]

< / BR>
The target compound was obtained by a method similar to that described in example 1.

So pl. 148-150aboutC (after recrystallization from ethanol)

FAB-MS (m/z): 374 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): and 3.72 (3H, s); 6,76 (1H, DD, j=7,6, 4,8 Hz); 6, 90-6,98 (3H, m), 7,05 (1H, TD, j=8.0 a, and 0.8 Hz); 7,13-7,20 (2H, m); EUR 7.57 (2H, d, j=8,8 Hz); of 7.82 (1H, d, j=2,8 Hz); 7,95 (1H, t, j=8.0 Hz); 8,01 (1H, DD, I=4,8, and 1.6 Hz); 9,76 (1H, s).

Elemental analysis for C18H16FN3O3S:

Calculated: C 57,90; H 4,32; N 11,25

Found: C 57,93; H of 4.57; N 10,98

P R I m e R 10.

N-[2-[(3-forefeel)amino]-3-pyridyl]-4-methoxybenzoyl-sulfonamide

[chemical formula 48]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 180-181aboutC (after recrystallization from ethanol)

FAB-MS (m/z): 374 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): at 3.69 (3H, s); to 6.67 (1H, TD, j=8,4); for 6.81 (1H, DD, j= 7,6, 4,8 Hz); 6,92 (2H, d, j=8,8 Hz); to 7.09 (1H, DD, j=8,4, 2.0 Hz); 7,22 (1H, dt, j=8,4, 6,8 Hz); 7,31 (1H, DD, j=7,6, and 1.6 Hz); 7,49 (1H, dt, I= 2,0, And 12.4 Hz). 7,56 (2H, d, j=8,8 Hz); with 8.05 (1H, DD, j=4,8, and 1.6 Hz); to 8.12 (1H, s); 9,52 (1H, Shir. C).

Elemental
P R I m e R 11.

N-[2-[(4-forfinal)amino]-3-pyridyl]-4-methoxybenzoyl-sulfonamide

[chemical formula 49]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 196-197aboutC (after recrystallization from ethanol)

FAB-MS (m/z): 374 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 3,71 (3H, c); 6,72 (1H, DD, j=4,8 and 7.6 Hz); to 6.95 (2H, d, j= 8,8 Hz);? 7.04 baby mortality (2H, t, j=8,8 Hz); of 7.25 (1H, DD, j=1,6 and 7.6 Hz); 7,42 (2H, m); 7,58 (2H, d, j=8,8 Hz); of 7.95 (1H, Shir. C); 7,98 (1H, DD, I=1,6, 4,8 Hz); 9,48 (1H, Shir. C).

Elemental analysis for C18H16FN3O3S:

Calculated: C 57,90; H 4,32; N 11,25

Found: C 57,83; H 4,32; N 11,21

P R I m e R 12.

N-(2-aniline-3-pyridyl)baselslt - named

[chemical formula 50]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 148-150aboutC (after recrystallization from methanol)

FAB-MS (m/z): 326 ([M+H]+)1H-NMR (DMCO-d6) (ppm): 6.73 x (1H, DD, j= 7,6, 4,8 Hz); 6.87 in-6,93 (1H, m); 7.18 in-7,24 (2H, m); of 7.25 (1H, DD, j=7,6, and 1.6 Hz); 7,41-7,47 (2H, m); 7,74-7,51 (2H, m); 7,51-EUR 7.57 (1H, m); to 7.67-7,72 (2H, m); of 7.90 (1H, s); 7,99 (1H, DD, I=4,8, and 1.6 Hz); 9,73 (1H, s).

Elemental analysis for C17H15N3O2S:

Calculated: C 62,75; H 4,65; N 12,91

Found: 63,03; H 4,74; N 12,67

P R I m e p 13. 4-Methoxy-N-[2-[(3-who got way described in example 1.

So pl. 161-162aboutC (after recrystallization from ethanol)

FAB-MS (m/z): 386 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 3,67, 3,70 (3H x 2); 6,47 (1H, DD, j=8,0, 2.0 Hz); of 6.73 (1H, DD, j=8.0 a, 4,8 Hz); 6,93 (2H, d, j=8,8 Hz); 6,97 (1H, DD, j= 8,0, 2.0 Hz); 7,10 (1H, t, j=8.0 Hz); 7,13 (1H, t, j=2.0 Hz); 7.29 trend (1H, DD, I= 8,0, 1,6 Hz); to 7.59 (2H, d, j=8,8 Hz); 7,89 (1H, s); 8,01 (1H, DD, j=4,8, and 1.6 Hz); of 9.55 (1H, s).

Elemental analysis for C19H19N3O4S:

Calculated: 59,21; H equal to 4.97; N 10,90

Found: C 59,14; H 4,96; N A 10.74

P R I m e R 14.

4-Hydroxy-N-[2-[(4-hydroxyphenyl)AMI - but]-3-pyridyl]benzosulfimide

[chemical formula 52]

< / BR>
The compound obtained in example 4 was dissolved in dimethylformamide and to this solution was added five equivalents meantioned sodium. The resulting solution was heated at 100aboutFrom and after processing the received target connection.

So pl. 252-257aboutC (decomp. ) (after recrystallization from a mixture of ethanol and water)

FAB-MS (m/z): 358 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 6,60 (1H, DD, j=7,6, 4,8 Hz); of 6.65 (2H, d, j= 8,8 Hz); for 6.81 (2H, d, j=8,8 Hz); 7,14 (1H, DD, j=7,6, and 1.6 Hz); 7,19 (2H, d, j= 8,8 Hz); 7,52 (2H, d, j=8,8 Hz); to 7.61 (1H, s); 7,87 (1H, DD, j=4,8, 1,6 Hz); 9,01 (1H, s); 9,39 (1H, s); 10,42 (1H, s).

P R I m e R 15.

N-[2-[(3,4-acid), ampelocera way described in example 1.

So pl. 126-127aboutC (after recrystallization from ethanol)

FAB-MS (m/z): 415 (M+)

1H-NMR (DMCO-d6) (ppm): 3.72 points, to 3.73 (3H x 3); of 6.66 (1H, DD, j=8,0, 3.6 Hz); for 6.81 (1H, d, j=8,8 Hz); of 6.96-6,98 (3H, m); 7,02 (1H, s); 7,21 (1H, DD, j= 8,0, 1.2 Hz); of 7.60 (2H, d, j=8.0 Hz); 7,73 (1H, s); of 7.95 (1H, DD, j=3,6, 1.2 Hz); of 9.45 (1H, Shir. C).

Elemental analysis for C20H21N3O5S:

Calculated: C 57,82; H 5,10; N 10,12

Found: C 57,73; H 5,10; N 10,07

P R I m e R 16.

4-Methoxy-N-[(2-[(2-methoxyphenyl)AMI - but]-3-pyridyl]benzosulfimide

[chemical formula 54]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 159-160aboutC (after recrystallization from ethanol)

FAB-MS (m/z): 386 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): of 3.78 (3H, s); the 3.89 (3H, s); 6,69 (1H, DD, j= 7,6, 4,8 Hz); 6.87 in-6,90 (2H, m); of 6.96-7,01 (2H, m), 7,05 (2H, d, j=8,8 Hz); 7,66 (2H, d, j= 8,8 Hz); 8,08 (1H, DD, j=4,8, and 1.6 Hz); 8,10 (1H, s); of 8.40 (1H, DD, I=6,4, 2,8 Hz); 9,78 (1H, s).

Elemental analysis for C19H19N3O4S:

Calculated: C 59,21; H equal to 4.97; N 10,90

Found: C 59,16; H 5,01; N 10,96

P R I m e R 17. 4-Methoxy-N-[2-[(3-methoxyphenyl)AMI-but]-3-pyridyl]benzosulfimide

[chemical formula 55]

< / BR>
The target compound was obtained by a method described in the UP>1H-NMR (DMCO-d6) (ppm): and 2.26 (3H, s); 3,71 (3H, s); of 6.71-6.73 x (2H, m); to 6.95 (2H, d, j=7,6 Hz); to 7.09 (1H, t, j=7,6 Hz); 7,16 (1H, s); 7,25-7,27 (2H, m); to 7.59 (2H, d, j=7,6 Hz); of 7.90 (1H, s); 8,00 (1H, DD, j=2,8, 1,6 Hz); at 9.53 (1H, Shir. C).

Elemental analysis for C19H19N3O3S:

Calculated: C 61,71; H 5,18; N 11,38

Found: C 61,79; H 5,18; N 11,46

P R I m e R 18.

4-Methoxy-N-[2-[(2-were)amino]-3-pyridyl]benzosulfimide

[chemical formula 56]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 147-148aboutC (after recrystallization from ethanol)

FAB-MS (m/z): 370 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): to 2.06 (3H, s); of 3.77 (3H, s); of 6.65 (1H, DD, j= 7,6, 4,8 Hz); 6,92 (1H, t, j= 7,6 Hz); 7.03 is (2H, d, j=8,8 Hz); to 7.09 (1H, t, j= 7,6 Hz); 7,11-to 7.15 (2H, m); 7,53 (1H, s); of 7.55 (1H, d, j=7,6 Hz); 7,63 (2H, d, j=8,8 Hz); to $ 7.91 (1H, DD, j=4,8, and 1.6 Hz); 9,67 (1H, s).

Elemental analysis for C19H19N3O3S:

Calculated: C 61,77; H 5,18; N 11,38

Found: C 61,80; H 5,17; N 11,40

P R I m e R 19.

N-(2-aniline-3-pyridyl)-4 - hydroxybenzenesulfonate

[chemical formula 57]

< / BR>
The target compound by treating the compound of example 3 by the method described in example 14.

So pl. 226-228aboutC (after recrystallization from methanol)

FAB-MS (m/z): 342 (C); 7,21-7,27 (2H, m); 7,46-7,51 (2H, m), 7,52 (2H, d, j=8,8 Hz); a 7.92 (1H, s); of 7.97 (1H, DD, j= 4,8, and 1.6 Hz); 9,50 (1H, s); the 10.40 (1H, c).

P R I m e R 20.

N-(2-aniline-3-pyridyl)-4-nitroben - solarpanel

[chemical formula 58]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 191-192aboutC (after recrystallization from ethanol)

FAB-MS (m/z): ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 6,80-6,83 (2H, m); for 7.12 (2H, t, j=8,4 Hz); of 7.25 (2H, d, j= 8,4 Hz); 7,40 (1H, DD, j=1,6 and 7.6 Hz); 7,83 (3H, d, j=8,8 Hz); 8,07 (1H, Shir. C); 8,19 (2H, d, j=8,8 Hz); to 9.91 (1H, Shir. C).

Elemental analysis for C17H14N4O4S:

Calculated: C 55,13; H 3,81; N 15,13

Found: C 55,17; H of 3.97; N 14,77

P R I m e R 21.

4-Amino-N-(2-aniline-3-pyridyl)Ben-solarpanel

[chemical formula 59]

< / BR>
The target compound was obtained by catalytic reduction of the compound obtained in example 20 in the presence of palladium charcoal in a standard way.

So pl. 228-230aboutC (after recrystallization from ethanol)

FAB-MS (m/z): 341 ([M+H]+)

1H-NMR (DMCO-d6) (ppm); 5,99 (2H, Shir. C); 6,50 (2H, d, j=8,8 Hz); 6,70 (1H, DD, j=4,4, 7,6 Hz); 6,91 (1H, dt, I=0,8, 7,2 Hz); 7.18 in (1H, DD, j= 1,6 and 7.6 Hz); 7,24 (2H, t, j=7,6 Hz); 7,33 (2H, d, j=8,8 Hz); 7,53 (2H, dt, I=1,2, 7,6 Hz); 7.95 is 8; H 4,74; N 16,46

Found: C 60,08; H of 4.67; N 16,23

P R I m e R 22.

N-(2-aniline-3-pyridyl)-3,4-dimethoxybenzenesulfonamide

[chemical formula 60]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 171-172aboutC (after recrystallization from ethanol)

FAB-MS (m/z): 386 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): to 3.64 (3H, s); of 3.69 (3H, s); of 6.75 (1H, DD, j= 4,8 and 7.6 Hz); to 6.88 (1H, t, j=7,6 Hz); 6,93 (1H, d, j=8,8 Hz); 7,10 (1H, d, j= 2.0 Hz); 7,17-7,22 (3H, m); to 7.32 (1H, d, j=7,6 Hz); 7,39 (2H, d, I=8.0 Hz); 7,89 (1H, Shir. C); 8,00 (1H, d, j=4,8 Hz); 9,48 (1H, Shir. C).

Elemental analysis for C19H19N3O4S:

Calculated: C 59,21; H equal to 4.97; N 10,90

Found: C 59,22; H 4,91; N 10,63

P R I m e R 23.

4-Hydroxy-N-[2-[(4-methoxyphenyl)AMI - but]-3-pyridyl]benzosulfimide

[chemical formula 61]

< / BR>
The target compound was obtained by the method described in example 14.

So pl. 214-216aboutC (after recrystallization from a mixture of ethanol and water).

FAB-MS (m/z): 372 ([M+H]+)

1H-NMR (DCMO-d6) (ppm): 3,71 (3H, s); 6,63 (1H, DD, j=7,6, 4,8 Hz); to 6.80 (2H, d, j= 8,8 Hz); PC 6.82 (2H, d, j=8,8 Hz); 7,16 (1H, DD, j=7,6, and 1.6 Hz); to 7.35 (2H, d, j=8,8 Hz); 7,51 (2H, d, j=8,8 Hz); of 7.75 (1H, s); of 7.90 (1H, DD, I=4,8, and 1.6 Hz); 9,41 (1H, s); 10,42 (1H, s).

Elemental analysis for C18H17-aniline-3-pyridyl)-4-chlorobenz - solarpanel

[chemical formula 62]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 186-188aboutC (after recrystallization from ethanol)

FAB-MS (m/z): 360 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 6,77 (1H, DD, j=7,6, 4,8 Hz); 6.90 to (1H, dt, j= 7,6, and 0.8 Hz); 7,22 (2H, t, j=7,6 Hz); 7,30 (1H, DD, j=7,6, 1.2 Hz); 7,38 (2H, DD, j= 7,6, and 0.8 Hz); 7,51 (2H, d, j=8,4 Hz); to 7.64 (2H, d, j=8,4 Hz); 7,89 (1H, s); 8,02 (1H, DD, j=4,8, 1.2 Hz); 9,76 (1H, Shir. C).

Elemental analysis for C17H14ClN3O2S:

Calculated: C 56,74; H to 3.92; N 11,68

Found: C 56,79; H is 4.03; N 11,67

P R I m e R 25.

N-(2-aniline-3-pyridyl)-3-chlorobenz - solarpanel

[chemical formula 63]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 143-144aboutC (after recrystallization from ethanol)

FAB-MS (m/z): 360 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 6,77 (1H, DD, j=7,6, 4,8 Hz); 6,91 (1H, dt, j= 7,6, 1.2 Hz); 7,21 (2H, t, j=7,6 Hz); to 7.32 (1H, DD, j=7,6, and 1.6 Hz); 7,41 (2H, DD, j= 7,6, 1.2 Hz); 7,46 (1H, t, j=8.0 Hz); 7,54-to 7.61 (2H, m); to 7.68 (1H, Shir. C); a 7.92 (1H, Shir. C); 8,04 (1H, DD, j=4,8, and 1.6 Hz); 9,80 (1H, Shir. C).

Elemental analysis for C17H14ClN3O2S:

Calculated: C 56,74; H to 3.92; N 11,68

Found: C 56,73; H 4.09 to; S 11,68

P R I m e R 26.

N-(2-aniline-3-pyridyl)-3-mutivariate 1.

So pl. 161-162aboutC (after recrystallization from ethanol)

FAB-MS (m/z): 340 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 2,22 (3H, s); 6,74 (1H, DD, j=7,6, 4,8 Hz); 6.90 to (1H, dt, j= 7,2, 1.2 Hz); 7,21 (2H, t, j=7.2 Hz); 7,27-to 7.35 (3H, m); 7,42 (2H, DD, j=7,2, 1.2 Hz); was 7.45 (1H, TD, j=7,2, 2.0 Hz); 7,52 (1H, Shir. C); a 7.92 (1H, s); 8,00 (1H, DD, j=4,8, 1.2 Hz); 9,68 (1H, Shir. C).

Elemental analysis for C18H17N3O2S:

Calculated: C 63,70; H of 5.05; N 12,38

Found: C expenses 63.81; H 5,16; N 12,43

P R I m e R 27.

N-(2-aniline-3-pyridyl)-4-ethoxybenzylidene

[chemical formula 65]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 161-162aboutC (after recrystallization from ethanol)

FAB-MS (m/z): 370 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 1.26 in (3H, t, j=7.0 Hz); of 3.94 (2H, sq I=7,0 Hz); 6,74 (1H, DD, j=7,6, 4,8 Hz); 6.89 in (1H, TT, j=7,2, 0.8 Hz); 6,92 (2H, d, j= 8,8 Hz); 7,21 (2H, t, j=7.2 Hz); 7,27 (1H, DD, j=7,6, and 1.6 Hz); 7,42 (2H, DD, I=to 7.2, 0.8 Hz); EUR 7.57 (2H, d, j=8,8 Hz); 7,88 (1H, s); 7,99 (1H, DD, j=4,8, and 1.6 Hz); at 9.53 (1H, Shir. C).

Elemental analysis for C19H19N3O3S:

Calculated: C 61,77; H 5,18; N 11,37

Found: C 61,72; H 5,31; N 11,43

P R I m e R 28.

4-Acetylamino-N-(2-aniline-3-Piri - DIL)benzosulfimide

[chemical formula 66]

< / BR>
The target connection the floor of the BR> FAB-MS (m/z): 383 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 2,04 (3H, s); 6,72 (1H, DD, j=7,6, 4,8 Hz); 6.90 to (1H, TT, j=8,0, 1.2 Hz); 7,19-7,24 (3H, m); was 7.45 (2H, DD, j=8,0, 1.2 Hz); of 7.60 (2H, d, j=9,2 Hz); the 7.65 (2H, d, j=9,2 Hz); to $ 7.91 (1H, s); 7,98 (1H, DD, I=4,8, and 1.6 Hz); a 9.60 (1H, Shir. C); 10,23 (1H, Shir. C).

Elemental analysis for C19H18N4O3S:

Calculated: C 59,67; H 4,74; N 14,65

Found: C 59,69; H 4,82; N 14,38

P R I m e R 29.

N-(2-aniline-3-pyridyl)-4-venexia - solarpanel

[chemical formula 67]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 164-166aboutC (after recrystallization from ethanol)

FAB-MS (m/z): 418 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): is 6.78 (1H, DD, j=7,6, 4,8 Hz); at 6.84 (2H, DD, j= 7,6, 1.2 Hz); 6,91-of 6.96 (3H, m); 7,19-7,27 (3H, m); of 7.36-7,40 (3H, m); 7,44 (2H, DD, j=7,6, 1.2 Hz); a 7.62 (2H, d, j=9,2 Hz); a 7.85 (1H, s); 8,02 (1H, DD, I=4,8, and 1.6 Hz); 9,62 (1H, Shir. C).

Elemental analysis for C23H19N3O3S:

Calculated: C 66,17; H 4,59; N 10,06

Found: C 66,15; H to 4.68; N 10,04

P R I m e R 30.

N-(2-aniline-3-pyridyl)-4-tianamen-solarpanel

[chemical formula 68]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 155-157aboutC (after recrystallization from methanol)

FAB-MS (m/z): 35 Hz); of 7.36 (1H, DD, j= 7,6, and 1.6 Hz); 7,76 (2H, d, j=7,6 Hz); 7,86-7.89 (3H, m); with 8.05 (1H, width); for 9.90 (1H, Shir. C).

Elemental analysis for C18H14N4O2S:

Calculated: C 61,70; H is 4.03; N 15,99

Found: C 61,73; H 4,14; N OF 15.75

P R I m e R 31.

N-(2-aniline-3-pyridyl)-2,4-demeton-dibenzalacetone

[chemical formula 69]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 176-178aboutC (after recrystallization from ethanol)

FAB-MS (m/z): 386 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 3,76 (3H, s); 3,81 (3H, s); 6,53 (1H, DD, j= 8,8, 2,4 Hz); 6,59 (1H, d, j=2.4 Hz); 6,69 (1H, DD, j=7,6, 4,8 Hz); 6,92 (1H, t, j= 7,6 Hz); of 7.25 (2H, t, j=7,6 Hz); 7,33 (1H, DD, j=7,6, and 1.6 Hz); to 7.50 (2H, d, j= 7,6 Hz); at 7.55 (1H, d, j=8,8 Hz); a 7.92 (1H, DD, j=4,8, and 1.6 Hz); 8,07 (1H, s).

Elemental analysis for C19H19N3O4S:

Calculated: C59,21; H equal to 4.97; N 10,90

Found: C 59,19; H 5,04; N 10,91

P R I m e R 32.

N-(2-aniline-3-pyridyl)-2-chlorobenz - solarpanel

[chemical formula 70]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 140-141aboutC (after recrystallization from toluene)

FAB-MS (m/z): 360 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 6,72 (1H, DD, j=7,6, 4,8 Hz); 6,93 (1H, t, j= 7,6 Hz); of 7.25 (2H, t, j=7,6 Hz); 7,31 (1H, DD, j=7,6, and 1.6 Hz); 7,42-7,417H14ClN3O2S:

Calculated: C 56,74; H to 3.92; N 11,68

Found: C 56,86; H 4,06; N ARE 11.62

P R I m e R 23.

4-Acetyl-N-(2-aniline-3-pyridyl)Ben-solarpanel

[chemical formula 71]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 171-173aboutC (after recrystallization from ethanol)

FAB-MS (m/z): 368 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): to 2.46 (3H, s); is 6.78 (1H, DD, j=7,6, 4,8 Hz); 6,85 (1H, t, j= 7,6 Hz); 7,15 (2N, so I=7,6 Hz); 7,31 (2H, DD, j=7,6, 1.2 Hz); to 7.35 (1H, DD, j=7,6, and 1.6 Hz); 7,74 (2H, d, j=8,4 Hz); a 7.85 (1H, s); 7,94 (2H, d, j=8.4 Hz); 9,03 (1H, DD, j=4,8, and 1.6 Hz); 9,83 (1H, Shir. C).

Elemental analysis for C19H17N3O3S:

Calculated: C 62,11; H of 4.66; N 11,44

Found: C 62,31; H 4,78; N 11,19

P R I m e R 34. N-[2-[(3-hydroxyphenyl)amino]-3-Piri-DIL]-4-methoxybenzenesulfonamide

[chemical formula 72]

< / BR>
4.0 g (19,9 mm) of the compound obtained in the example of obtaining 6 were subjected to interaction with 4.11 g (19,9 mm) p-methoxybenzenesulfonamide, after which the product was processed in the manner described in example 1, resulting in a received 5.0 g of the target compound.

So pl. 181-182aboutC (after recrystallization from toluene)

FAB-MS (m/z): 372 ([M+H]+)

1H-NMR (DMCO-d6) (ppm) to 7.25 (1H, DD, j=7,6, and 1.6 Hz); to 7.59 (2H, d, j=8,8 Hz); to 7.77 (1H, s); 7,99 (1H, DD, j=4,8, and 1.6 Hz); 9,18 (1H, s); by 9.56 (1H, Shir. C).

Elemental analysis for C18H17N3OL3S:

Calculated: C 58,21; H br4.61; N 11,31

Found: C 58,26; H of 4.67; N 10,99

P R I m e R 35.

N-[2-[(4-ethoxyphenyl)amino]-3-pyridyl]-4 methoxybenzenesulfonamide

[chemical formula 73]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 144-146aboutC (after recrystallization from ethanol)

FAB-MS (m/z): 400 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): is 1.31 (3H, t, j=2,8 Hz); of 3.73 (3H, s); of 3.97 (2H, sq I=2,8 Hz); of 6.65 (1H, DD, j=4,8 and 7.6 Hz); to 6.80 (2H, d, j=8,8 Hz); 6,98 (2H, d, j= 8,8 Hz); 7,21 (2H, DD, j=1,6 and 7.6 Hz); 7,28 (2H, d, j=8,8 Hz); of 7.60 (2H, d, j=8,8 Hz); 7,72 (1H, Shir. C); a 7.92 (1H, DD, I=1,6, 4,8 Hz); for 9.47 (1H, Shir. C).

Elemental analysis for C20H21N3O4S:

Calculated: C 60,13; H and 5.30; N 10,52

Found: C 60,02; H 5,27; N OF 10.21

P R I m e R 36. N-[2-[(4-hydroxy-3-were)amino]-3-pyridyl]-4-methoxybenzenesulfonamide

[chemical formula 74]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 89-91aboutC (after recrystallization from toluene)

FAB-MS (m/z): 386 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 2,07 (3H, s); of 3.75 (3H, s); 6,60 (1H, DD, j= 4,8, 7.6 G is); 8,87 (1H, s); 9,44 (1H, Shir. C).

Elemental analysis for C19H19N3O4S:

Calculated: C 59,21; H equal to 4.97; N 10,90

Found: C 58,97; H is 5.06; N 10,53

P R I m e R 37.

Ethyl-4-[[3-(4-methoxybenzenesulfonyl-Mido)-2-pyridyl]amino]-benzoate

[chemical formula 75]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 172-173aboutC (after recrystallization from ethanol)

FAB-MS (m/z): 428 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): is 1.31 (3H, t, j=3.2 Hz); 3,63 (3H, s); 4,27 (2H, sq I=3.2 Hz); to 6.88 (2H, d, j=8,8 Hz); to 6.88 (1H, DD, j=4,8 and 7.6 Hz); 7,38 (1H, DD, j= 1,6 and 7.6 Hz); 7,51 (2H, d, j=8,8 Hz); rate of 7.54 (2H, d, j=8,8 Hz); 7,80 (2H, d, j=8,8 Hz); 8,10 (1H, DD, I=1,6, 4,8 Hz); a 8.34 (1H, Shir. C); 9,58 (1H, Shir. C).

Elemental analysis for C21H21N3O3S:

Calculated: C 59,00; H of 4.95; N 9,83

Found: C 59,98; H 4,91; N 9,63

P R I m e R 38.

4-Methoxy-N-[2-[(4-methylthiophenyl)AMI - but]-3-pyridyl]-benzosulfimide

[chemical formula 76]

< / BR>
The target compound was obtained by a method similar to that described in example 1.

So pl. 148-149aboutC (after recrystallization from ethanol)

FAB-MS (m/z): 402 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 2,43 (3H, s); 3,70 (3H, s); of 6.73 (1H, DD, j= 4,8 and 7.6 Hz); 6,94 (2H, d, j=8,8 Hz); 7,17 (2H, d, j=8,8 Hz); 7,26 is entry analysis for C19H19N3O3S:

Calculated: C 56,84; H of 4.77; N 10,47

Found: C 56,90; H of 4.77; N 10,24

P R I m e R 39.

4-[[3-(4-Methoxybenzenesulfonamide)-2-pyridyl]amino]persulfate potassium

[chemical formula 77]

< / BR>
2.0 g (5,38 mm) of the compound of example 6 was dissolved in 20 ml of pyridine. To the solution at -15 -10aboutWith one drop was added 800 mg (6,87 mm) chlorosulfonic acid 95% Then the temperature was slowly raised to room temperature and the mixture is stirred for 3 days. To bring the pH to 8-9 to the reaction mixture were added 1N aqueous potassium carbonate. The solvent is kept at reduced pressure. To the residue were added water and ethyl acetate, and the resulting aqueous layer was separated, concentrated, and was purified by column chromatography on silica gel, and precipitated with methanol/dichloromethane, resulting in received 1,58 g of target compound.

So pl. 165-166aboutWITH

FAB-MS (m/z): 528 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): to 3.73 (3H, s); of 6.68 (1H, DD, j=4,8, 8.0 Hz); 6,98 (2H, d, j=8,8 Hz); 7,02 (2H, d, j=8,4 Hz); 7,25-7,27 (3H, m); to 7.61 (2H, d, j=8,8 Hz); 7,83 (1H, s); 7,94 (1H, DD, I=1,2, 4,8 Hz); of 9.55 (1H, s).

Elemental analysis for C18H16N3O7S2K x x3/2H2O:

Calculated: C 41,85; H 3,71; N 8,13

Found: C 41,88; H 3 the chemical formula 78]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 174-176aboutC (after recrystallization from ethanol)

FAB-MS (m/z): 448 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 3,75 (3H, s), 6,72 (1H, DD, j=4,8 and 7.6 Hz), 6,92 (2H, d, j=8,8 Hz); 6,91-6,97 (2H, m); of 6.96 (2H, d, j=8,8 Hz), 7,05-7,10 (1H, m), 7,27 (1H, DD, j=1,6 and 7.6 Hz), 7,32-7,40 (2H, m), the 7.43 (2H, d, I=8,8 Hz), to 7.59 (2H, d, j=8,8 Hz), 7,92 (1H, Shir. C) 7,98 (1H, DD, I=1,6, 4,8 Hz), 9,44 (1H, Shir. C).

Elemental analysis for C24H21N3O4S:

Calculated: C 64,41; H to 4.73; N 9,39

Found: C 64,71; H 4,96; N OF 9.30

P R I m er 41.

4-[[3-(4-Methoxybenzenesulfonamide)-2-pyridyl]amino]benzoic acid.

[chemical formula 79]

< / BR>
The target compound was obtained by alkaline hydrolysis of the compound of example 37, carried out in a standard way.

So pl. 238-250aboutC (after recrystallization from ethanol)

FAB-MS (m/z): 400 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): to 3.64 (3H, s), 6.87 in (1H, DD, j=4,8 and 7.6 Hz), 6.89 in (2H, d, j= 8,8 Hz), 7,37 (1H, DD, j=1,6 and 7.6 Hz), 7,49 (2H, d, j=8,8 Hz), 7,54 (2H, d, j=8,8 Hz), 7,78 (2H, d, j=8,8 Hz), of 8.09 (1H, DD, I=1,6, 4,8 Hz), 8,29 (1H, Shir. C) 9,58 (1H, Shir. C) to 12.44 (1H, Shir.).

Elemental analysis for C19H17N3O5S:

Calculated: C 57,13; H 4,29; N 10,52

Found: C 57,10; H 4,42; N the I formula 80]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 205-207aboutC (decomp.) (after recrystallization from ethanol)

FAB-MS (m/z): 390 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 3,70 (3H, s), is 6.78 (1H, DD, j=7,6, 4,8 Hz), 6,93 (2H, d, j=8,8 Hz), 7,24 (2H, d, j=8,8 Hz), 7,30 (1H, DD, j=7,6, 20 Hz) was 7.45 (2H, d, j= 8,8 Hz), 7,56 (2H, d, j=8,8 Hz), 8,02 (1H, DD, j=4,8, 2.0 Hz), with 8.05 (1H, s), of 9.51 (1H, Shir. C).

Elemental analysis for C18H16ClN3O3S:

Calculated: C 55,46; H 4,14; N 10,78

Found: C 55,44; H 4,32; N 10,71

P R I m e 43.

N-[-2-[(2-hydroxyphenyl)amino]-3-Piri - DIL]-4-methoxybenzenesulfonamide

[chemical formula 81]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 154-155aboutC (after recrystallization from toluene)

FAB-MS (m/z): 372 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 3,81 (3H, s), 6,63 (1H, DD, j=8.0 a, 5,2 Hz), 6,72-6,79 (2H, m), 6,82-6,86 (2H, m), 7,07 (2H, d, j=8,8 Hz), 7,66 (2H, d, j= 8,8 Hz), with 8.05 (1H, DD, j=5,2, 1,6 Hz), 8,15 (1H, s), 8,29 (1H, DD, j=7,6, 2.0 Hz), to 9.70 (1H, s), 9,94 (1H, s).

Elemental analysis for C18H17N3O4S:

Calculated: C 58,22, H br4.61, N 11,32

Found: C 58,39, H 4,60, N 11,20

P R I m e R 44.

N-(2-aniline-3-pyridyl)-2,4,6-trim - telesolutions

[chemical formula 82] the recrystallization from ethanol)

FAB-MS (m/z): 368 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): of 2.16 (3H, s), 2,41 (6N, C) 6,70 (1H, DD, j= 7,6, 4,8 Hz), 6.89 in-6,94 (3H, m), was 7.08 (1H, DD, j=7,6, and 1.6 Hz), 7,24 (2H, t, j= 7,6 Hz), the 7.43 (2H, d, j=7,6 Hz), 7,89 (1H, s), 8,01 (1H, DD, j=4,8, and 1.6 Hz), 9,58 (1H, s).

Elemental analysis for C20H21N3O2S:

Calculated: C 65,37, H 5,76, N 11,43

Found: C 65,45, H 5,67, N 11,34

P R I m e R 45.

N-(2-aniline-3-pyridyl)-chloro-2,5-di - methylbenzenesulfonamide

[chemical formula 83]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 153-154aboutC (after recrystallization from ethanol)

FAB-MS (m/z): 388 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 2,20 (3H, s) to 2.41 (3H, s), of 6.75 (1H, DD, j= 7,6, 4,8 Hz) 6,91 (1H, t, j=7,6 Hz), 7.23 percent (2H, t, j=7,6 Hz), 7,26 (1H, DD, j= 7,6, and 1.6 Hz), 7,33 (1H, s), 7,38 (2H, d, j=7,6 Hz), 7,63 (1H, s), to 7.93 (1H, s), 8,02 (1H, DD, j=4,8, and 1.6 Hz), 9,76 (1H, s).

Elemental analysis for C19H18ClN3O2S:

Calculated: C 58,83, H 4,68, N 10,83

Found: C 58,97, with 4.64 H, N 10,85

P R I m e R 46. 4-Methoxy-N-[2-[(2-methoxy-5-pyridyl)amino]-3-pyridyl] benzosulfimide

[chemical formula 84]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 159-160aboutC (after recrystallization from ethanol)

FAB-MS (m/z): z), of 7.60 (2H, d, j=8,8 Hz), 7,72 (1H, DD, j=8,8 Hz), of 7.90 (1H, s), to 7.93 (1H, DD, j=4,8, 1.2 Hz), 8,13 (1H, d, j=2,8 Hz), 9,44 (1H, Shir. C).

Elemental analysis for C18H18N4O4S:

Calculated: C 55,95; H 4,69; N 14,50

Found: C 55,95, H 4.72 in, N OF 14.46

P R I m e R 47.

N-(4-aniline-6-methoxy-5-pyrimidyl)-4-methoxybenzenesulfonamide

[chemical formula 85]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 159-160aboutC (after recrystallization from ethanol)

FAB-MS (m/z): 387 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): to 3.38 (3H, s), of 3.80 (3H, s), 7,01-7,07 (3H, m), 7,30 (2H, t, j=8.0 Hz), EUR 7.57 (2H, DD, j=8.0 a, and 0.8 Hz), and 7.6 (2H, d, j=8,8 Hz), to 8.20 (1H, s); with 8.33 (1H, s); 9,29 (1H, s).

Elemental analysis for C18H18N4O4S:

Calculated: C 55,95, H 4,70, N 14,50

Found: C 55,90, H 4,71, N 14,49

P R I m e R 48.

N-(4-aniline-6-chloro-5-pyrimidyl)-4-methoxybenzenesulfonamide

[chemical formula 86]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 174-175aboutC (recrystallized from ethanol)

FAB-MS (m/z): 391 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 3,75 (3H, c), 7,03 (2H, d, j=8,8 Hz); to 7.09 (1H, t, j=7,6 Hz); to 7.32 (2H, t, j=7,6 Hz); 7,46 (2H, d, j=7,6 Hz); the 7.65 (2H, d, j=8,8 Hz); 8,29 (1H, s); 8,63 (1H, s); 9,74 (1H, Shir. Snaidero: C 52,29, H OF 3.85, N 14,27

P R I m e R 49. N-(2-aniline-6-dimethylamino-3-Piri-DIL)-4-methoxy-benzosulfimide

[chemical formula 87]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 152-153oC (recrystallized from a mixture of ethyl acetate and hexane)

FAB-MS (m/z): 399 ([M+H]+)

1H-NMR (CDCl3) (ppm): 3.04 from (6N, C); a 3.83 (3H, s); 5,71 (1H, d, j=8,8 Hz); of 5.75 (1H, s); 6,59 (1H, d, j=8,8 Hz); 6,91-of 6.96 (3H, m); 7.24 to 7,28 (3H, m); 7,53 (2H, d, j=7,6 Hz); 7,72 (2H, d, j=9,2 Hz).

Elemental analysis for C20H22N4O3S:

Calculated: C 60,28, H 5.56mm, N 14,06

Found: C 60,21, H 5,47, N 13,92

P R I m e R 50.

N-(2-aniline-6-chloro-3-pyridyl)-4-methoxybenzenesulfonamide

[chemical formula 88]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 206-208aboutC (recrystallized from ethanol)

FAB-MS (m/z): 390 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 3,71 (3H, c); 6,79 (1H, d j=8.0 Hz); 6,93-of 6.99 (3H, m); 7,26 (3H, t, j=8.0 Hz); 7,38 (2H, d, j=8.0 Hz); to 7.61 (2H, d, j=9,2 Hz); 8,15 (1H, s); by 9.56 (1H, s).

Elemental analysis for C18H16ClN3O3S:

Calculated: C 55,46, H 4,14, N 10,78

Found: C 55,49, H of 4.04, N TO 10.62

P R I m e R 51.

N-(4-aniline-3-pyridyl)-4-methoxime - solarpanel

CLASS="ptx2">

So pl. 201-202aboutC (recrystallized from ethanol)

FAB-MS (m/z): 356 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 3,75 (3H, s); 6,92 (1H, d, j=6.4 Hz); to 6.95 (2H, d, j=8,8 Hz); 7,13-7,20 (3H, m); 7,39 (2H, t, j=8.0 Hz); to 7.67 (2H, d, j=8,8 Hz); for 7.78 (1H, s); of 7.82 (1H, d, j= 5.6 Hz).

Elemental analysis for C18H17N3O3S:

Calculated: C 60,83, H 4,82, N 11,82

Found: C 60,78, H 4,77, N 11,84

P R I m e R 52.

N-[2-[(4-Dimethylcarbamoyl)amino] -3-pyridyl] -4-methoxybenzenesulfonamide

[chemical formula 90]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 202-203aboutC (recrystallized from ethanol)

FAB-MS (m/z): 443 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 2,90 (3H, s); 3,03 (3H, s); and 3.72 (3H, s); 6,72 (1H, DD, j= 7,6, 4,8 Hz); of 6.96 (2H, d, j=8,8 Hz); 6,97 (2H, d, j=8,8 Hz); 7,26 (1H, DD, j= 7,6, and 1.6 Hz); 7,41 (2H, d, j=8,8 Hz); of 7.60 (2H, d, I=8,8 Hz); 7,94 (1H, s); of 7.97 (1H, DD, j=4,8, and 1.6 Hz); 9,52 (1H, Shir. C).

Elemental analysis for C21H22N4O5S:

Calculated: C 57,00, H 5,01, N 12,66

Found: C 57,35, H to 4.98, N 12,55

P R I m e R 53.

N-(4-aniline-5-pyrimidyl)-4-methoxy - benzosulfimide

[chemical formula 91)

< / BR>
The target compound was obtained by catalytic reduction of the compound of example 48 in the Dag ethanol)

FAB-MS (m/z): 357 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): to 3.73 (3H, s); 7,01 (2H, d, j=8,8 Hz); 7,05 (1H, t, j=8.0 Hz); 7,30 (2H, t, j=8.0 Hz); 7,50 (2H, d, j=6.0 Hz); to 7.64 (2H, d, j=8,8 Hz); 7,87 (1H, s); of 8.40 (1H, s); to 8.57 (1H, Shir. C).

Elemental analysis for C17H16N4O3S:

Calculated: C 57,29, H 4,53, N 15,72

Found: C 57,25, H 4,68, N 15,36

P R I m e R 54.

N-(2-aniline-6-methoxy-3-pyridyl)-4-methoxybenzenesulfonamide

[chemical formula 92]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 187-188aboutC (recrystallized from ethanol)

FAB-MS (m/z): 386 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 3,70 (3H, s); of 3.77 (3H, s); 6,11 (1H, d, j=8.0 Hz); 6.89 in (1H, t, j=7,6 Hz); to 6.95 (2H, d, j=9,2 Hz); 7,07 (1H, d, j=8.0 Hz); 7,22 (2H, t, j=7,6 Hz); the 7.43 (2H, d, j=7,6 Hz); 7,52 (2H, d, I=9,2 Hz); 7,83 (1H, Shir. C); 9,23 (1H, Shir. C).

Elemental analysis for C19H19N3O4S:

Calculated: C, 59, 21, H equal to 4.97, N 10,90

Found: C 59,32, H equal to 4.97, N 10,76

P R I m e R 55.

N-(4,5-dianilino-5 pirimidil)-4-IU - oxybenzenesulfonate

[chemical formula 93]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 149-151aboutC (recrystallized from a mixture of dichloromethane and n-hexane)

FAB-MS (m/z): 448 ([M+H]+)2N, d, j=8,8 Hz); 8,05 (2H, s); 8,11 (1H, s); of 8.90 (1H, s).

Elemental analysis for C23H21N5O3S:

Calculated: C 61,73, H 4,73, N 15,05

Found: C 61,91, H 4,72, N 15,74

P R I m e R 56.

4-Methoxy-N-[2-(methoxyphenyl)amino-3-pyridyl]benzosulfimide

[chemical formula 94]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 80-81aboutC (recrystallized from diisopropyl ether)

FAB-MS (m/z): 370 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): a 3.01 (3H, s); 3,82 (3H, s); 6,46-6,51 (2H, m); 6,78-6,84 (1H, m);? 7.04 baby mortality (2H, d, j=8,8 Hz; 7,11-7,17 (2H, m); 7,17 (1H, DD, j= 4,8, 8.0 Hz); the 7.65 (1H, DD, I=1,6, 8.0 Hz); to 7.68 (2H, d, j=8,8 Hz); to 8.14 (1H, DD, I=1,6, 4,8 Hz); of 9.30 (1H, Shir. C).

Elemental analysis of C19H19N3O3S:

Calculated: C 61,77, H 5,18, N 11,38

Found: 61,85, H 5,28, N 11,36

P R I m e R 57.

4-Methoxy-N-[2-[(2-pyrimidyl)amino]phenyl]-benzosulfimide

[chemical formula 95]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 193-195aboutC (recrystallized from ethanol)

FAB-MS (m/z): 357 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 3,70 (3H, s); 6,79-6,83 (3H, m); of 6.96 (1H, dt, I= 1,6, and 8.4 Hz); 7,01 (1H, DD, I=1,6, and 8.4 Hz); 7,19 (1H, dt, I=1,6, and 8.4 Hz); 7,47 (2H, d, j=8,8 Hz); 7,87 (1H, DD, I=1,6, 8,4 Hz)S:

Calculated: C 57,29, H 4,53, N 15,72

Found: C 57,18, H of 4.57, N 15,80

P R I m e R 58.

N-(2-anilinophenol)-4-methoxybenzo-sulfonamide

[chemical formula 96]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 140-142aboutC (recrystallized from ethanol)

FAB-MS (m/z): 345 (M+)

1H-NMR (DMCO-d6) (ppm): at 3.69 (3H, s); 6,66-6,72 (2H, m); for 6.81 (2H, d, j= 8,8 Hz); 6,76-6,87 (2H, m);? 7.04 baby mortality-7,17 (5H, m); from 7.24 (1H, Shir. C); 7,52 (2H, d, j=8,8 Hz); of 9.30 (1H, Shir. C).

Elemental analysis for C19H18N2O3S:

Calculated: C 64,39, H 5,12, N OF 7.90

Found: C 64,49, H 5,17, N TO 7.77

P R I m e R 59.

N-[2-[(4-Benzoyloxymethyl)amino]-3-PI - rider]-4-methoxybenzenesulfonamide

[chemical formula 97]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 208-210aboutC (recrystallized from methanol)

FAB-MS (m/z): 476 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): to 3.73 (3H, s); of 6.75 (1H, d, j=4,8 and 7.6 Hz); 6,98 (2H, d, j= 8,8 Hz); 7,13 (2H, d, j=8,8 Hz); 7,28 (1H, DD, j=1,6 and 7.6 Hz); 7,51 (2H, d, j= 8,8 Hz); to 7.61 (2H, d, j=8,8 Hz); 7,58-the 7.65 (2H, m); 7,72 for 7.78 (1H, m); 8,00 (1H, DD, I= 1,6, 4,8 Hz); 8,04 (1H, Shir. C); 8,11-8,16 (2H, m); 9,54 (1H, Shir. C).

Elemental analysis for C25H21N3O5S:

Calculated: C 63,15, H of 4.45, N Ridel] 4-methoxybenzenesulfonamide

[chemical formula 98]

< / BR>
The target compound was obtained by the method described in example 1.

1H-NMR (CDCl3) (ppm): 1,47 (N, C); is 3.82 (3H, s); 4,18 (2H, d, j=5.6 Hz); of 5.17 (1H, Shir. with); to 6.58 (2H, DD, j=7,6, 4,8 Hz); 6.89 in (1H, DD, j=7,6, and 1.6 Hz); make 6.90 (2H, d, j=8,8 Hz); 7,00 (2H, d, j=8,8 Hz); to 7.35 (1H, Shir. C); 7,47 (2H, d, j= 8,8 Hz); to 7.68 (2H, d, j=8,8 Hz); 8,10 (1H, DD, j=4,8, 1,6 Hz).

P R I m e R 61

N-[2-[[4-(aminoethoxy)phenyl] AMI-but] -3-pyridyl] -4 - methoxybenzenesulfonamide the dihydrochloride

[chemical formula 99]

2HCl

272 mg (0,515 mm) of the compound of example 60 was added to 10 ml of tetrahydrofuran. To the mixture was added 2 ml conc. hydrochloric acid and stirred for 3 hours at room temperature. The solvent is kept at room temperature. The solvent is kept under reduced pressure, and the residue was recrystallized from ethanol and resulted 159 g of target compound.

So pl. 196 to 199aboutC (decomp.)

FAB-MS (m/z): 429 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 3,71 (3H, s); 4,08-4,11 (2H, m); is 6.78 (1H, DD, j= 4,8 and 7.6 Hz); 6,94 (2H, d, j=8,8 Hz);? 7.04 baby mortality (2H, d, j=8,8 Hz); to 7.32 (1H, DD, j=1,6 and 7.6 Hz); of 7.48-7,51 (2H, m); to 7.61 (2H, d, j=8,8 Hz); of 7.97 (1H, DD, I=1,6, 4,8 Hz); 8,48 (3H, Shir. C); 9,84 (1H, Shir. C).

Elemental analysis for C20H20N4O5S x x2HCl1/2H2O:

Calculated: C 47,07, H alsultan - MFA

[chemical formula 100]

< / BR>
500 mg (1.3 mm) of the compound of example 4 was dissolved in 5 ml of dimethylformamide. To the solution was added 60 mg (1.5 mm) of sodium hydride (60%). The resulting solution was stirred at room temperature for 30 minutes, and then to the solution was added methyliodide.

After stirring overnight, the solvent is kept at reduced pressure. The residue was dissolved in ethyl acetate, and the solution was washed with water. After drying with magnesium sulfate, concentration and purification using column chromatography on silica gel, received 290 mg of the target compound.

FAB-MS (m/z): 400 ([M+H]+)

1H-NMR (DCl3) (ppm): 3.15 in (3H, s); of 3.80 (3H, s); 3,88 (3H, s); 6,50 (1H, DD, j= 4,8 and 7.6 Hz); to 6.67 (1H, DD, j=1,6 and 7.6 Hz); 6.89 in (2H, d, j=8,8 Hz); 6,98 (2H, d, j=8,8 Hz); 7.29 trend (1H, Shir. C); 7,47 (2H, d, j=8,8 Hz); the 7.65 (2H, d, j=8,8 Hz); of 8.09 (1H, DD, I=1,6, 4,8 Hz).

Elemental analysis for C20H21N3O4S:

Calculated: C 60,14, 5,30 H, N 10,52

Found: C 60,08, H 5,39, N 10,29

P R I m e R 63.

N-[2-[[4-(2-aminobenzoate)phenyl] AMI - but] -3-pyridyl] -4-methoxybenzenesulfonamide

[chemical formula 101]

< / BR>
500 mg (1.35mm) compound of example 6; 260 mg (1,59 mm) of the anhydride stoaway acid; and 170 mg (1,39 mm) 4-dimethylaminopyridine was dissolved Yali under reduced pressure and to the residue was added ethyl acetate. Formed in this way the residue was recrystallized from ethanol and obtained 500 mg of the target compound.

So pl. 221-225aboutC (decomp.)

FAB-MS (m/z): 491 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 3,74 (3H, s); 6,60 (1H, dt, I=1,6, and 8.4 Hz); 6.73 x (2N, Shir. C); 6,74 (1H, DD, j=4,8, 8.0 Hz); 6,83 (1H, DD, j=0,8, 8,4 Hz); 6,98 (2H, d, j=8,8 Hz); was 7.08 (2H, d, j=9,2 Hz); 7,27 (1H, DD, j=2,0, 8.0 Hz); 7,33 (1H, dt, I=1,6, 7,2 Hz); 7,49 (1H, d, j=9,2 Hz); to 7.61 (2H, d, j= 8,8 Hz); a 7.92 (1H, DD, I=1,6, and 8.4 Hz); 7,99 (1H, DD, j=2.0 a, 4,8 Hz); 8,02 (1H, s); a 9.60 (1H, Shir. C).

Elemental analysis for C25H22N4O5S:

Calculated: C 61,21, H to 4.52, N 11,42

Found: C 60,98, H to 4.52, N 11,24

P R I m e R 64.

4-[[3-(4-Methoxybenzenesulfonamide)-2-pyridyl] amino] phenyl (monopotassium phosphate)

[chemical formula 102]

< / BR>
7,44 g (20 mm) of the compound of example 6 are suspended in 100 ml of phosphorus oxychloride, and the resulting suspension was heated in a vessel with reflux condenser, resulting in the obtained homogeneous solution. Oxychloride of phosphorus drove away under reduced pressure, to the residue was added diisopropyl ether, and the formed solid substance was removed by filtration and suspended in 100 ml of tetrahydrofuran. To the suspension was added, the cooling in this ice, 50 ml of water and stirred until it's time paraml of methanol and 100 ml of water, and the resulting solution was concentrated under reduced pressure until, until it formed an insoluble substance. This substance was removed, and the residue was again concentrated under reduced pressure, the precipitate was separated by filtration and received 4,27 g of target compound.

So pl. 215-216aboutWITH

FAB-MS (m/z): 452 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): to 3.73 (3H, s); 6,70 (1H, DD, j=7,6, 4,8 Hz); 6,98 (2H, d, j= 8,8 Hz); 7,02 (2H, d, j=8,8 Hz); from 7.24 (1H, DD, j=7,6, and 1.6 Hz); to 7.35 (2H, d, j=8,8 Hz); of 7.60 (2H, d, j=8,8 Hz); 7,88 (1H, s); of 7.95 (1H, DD, I=4,8, and 1.6 Hz); 9,50 (1H, Shir. C).

Elemental analysis for C18H18N3O7PS:

Calculated: C 47,90, H is 4.03, N 9,31

Found: C 47,72, H 4.00, N 9,39

P R I m e R 65.

3-[[3-(4-Methoxybenzenesulfonamide)-2-pyridine]amino]phenyl monophosphate

[chemical formula 103]

< / BR>
120 mg of target compound was obtained by the reaction of interaction of 1.00 g (2.7 mm) of the compound of example 34 with 10 ml of phosphorus oxychloride, and the resulting product was treated in the manner described in example 64.

So pl. 166-168aboutWITH

FAB-MS (m/z): 452 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 3,70 (3H, s); of 6.73 (1H, d, j=7,6 Hz) 6,77 (1H, DD, j= 7,6, 4,8 Hz); to 6.95 (2H, d, j=8,8 Hz); to 7.15 (1H, t, j=7,6 Hz); 7,21 (1H, d, j=7,6 Hz); 7,30 (1H, DD, j=7,6, and 1.6 Hz); 7,37 (1H, s); to 7.59 (2H, d, I=8>PS x xH2O:

Calculated: C of 46.06, H 4,29, N 8,95

Found: C 46,16, H 4,13, N 8,83

P R I m e R 66.

4-Methoxy-N-[2-[[4-(4-methoxybenzyl - Livonians)phenyl]-amino]-3-pyridyl] benzosulfimide

[chemical formula 104]

< / BR>
The compound obtained in example 4, was subjected to a reaction between 4-methoxybenzenesulfonamide in an equivalent ratio of 1:2, resulting in a received target connection.

So pl. 122-123aboutC (recrystallized from ethanol)

FAB-MS (m/z): 542 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 3,71 (3H, s); 3,88 (3H, s); 6,76 (1H, DD, j= 7,6, 4,8 Hz); at 6.84 (2H, d, j=8,8 Hz); 6,94 (2H, d, j=8,8 Hz); 7,17 (2H, d, j= 8,8 Hz); of 7.25 (1H, DD, j=7,6, 1.2 Hz); 7,42 (2H, d, j=8,8 Hz); 7,56 (2H, d, j= 8,8 Hz); 7,76 (2H, d, j=8,8 Hz); 7,98 (1H, DD, j=4,8, 1.2 Hz); of 8.06 (1H, s); 9,51 (1H, Shir. C).

Elemental analysis for C25H23N3O7S3:

Calculated: C 55,40, H 4,28, N 7,76

Found: C 55,57, H 4.26 deaths, N TO 7.61

P R I m e R 67.

N-[2-[(4-hydroxyphenyl)amino]phenyl]-4-methoxybenzenesulfonamide

[chemical formula 105]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 163-164aboutC (recrystallized from ethanol)

FAB-MS (m/z): 370 (M+)

1H-NMR (DMCO-d6) (ppm): 3,76 (3H, emanny analysis for C19H18N2O4S:

Calculated: C 61,61, H 4,90, N 7,56

Found: C 61,86, H 4,90, N 7,39

P R I m e R 68.

4-Methoxy-N-[2-[(4-pivaloyloxymethyl) amino] -3-pyridyl]-benzolsulfonat-MFA

[chemical formula 106]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 188-189aboutC (recrystallized from toluene)

FAB-MS (m/z): 456 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 1,30 (N, C); and 3.72 (3H, s); of 6.73 (1H, DD, j= 7,6,4,8 Hz); 6,94 (2H, d, j=8,8 Hz); 6,97 (2H, d, j=8,8 Hz); of 7.25 (1H, DD, j= 7,6, and 1.6 Hz); was 7.45 (2H, d, j=8,8 Hz); of 7.60 (2H, d, j=8,8 Hz); 7,97-8,00 (2H, m); 9,52 (1H, Shir. C).

Elemental analysis for C23H25N3O5S:

Calculated: C 60,64, H of 5.53, N WHICH 9.22

Found: C 60,57, H 5,43, N 8,95

P R I m e R 69.

4-Methoxy-N-[2-[(4-pyridyl)amino]Fe-Neil]benzosulfimide

[chemical formula 107]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 185-187aboutC (recrystallized from ethanol)

FAB-MS (m/z): 356 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): to 3.67 (3H, s); 6,45 (2H, d, j=6.0 Hz); 6.73 x (2H, d, j= 8,8 Hz); 7,07 (1H, dt, j=7,6, 1.2 Hz); 7,16 (1H, dt, j=7,6, 1.2 Hz); 7,22 (1H, DD, j=7,6, 1.2 Hz); 7,28 (1H, DD, j=7,6, 1.2 Hz); was 7.45 (2H, d, I=8,8 Hz); of 7.90 (1H, Shir. C); with 8.05 (2H, d, j=6.0 Hz).

Elemental analysis for C18

N-[2-(4-Methoxybenzenesulfonamide)phenyl]-2-nicotine amide

[chemical formula 108]

< / BR>
0.97 g (7 mm) 2-methylnicotinic acid suspended in 4.5 ml of dichloromethane. To the solution was added to 1.33 g (16,8 mm) of pyridine, and then of 1.05 g (8.4 mm) of thionyl chloride. The resulting mixture was stirred at room temperature for 30 min, and then to this mixture was added a solution of 1.77 g (6,36 mm) of the compound obtained in example 12, in 7 ml of dichloromethane. Then the solution is stirred overnight, and then thereto was added a solution of sodium bicarbonate, and the product was extracted with dichloromethane. The solution was concentrated, and the concentrate was added ethanol, and the resulting crystals were isolated by filtration and recrystallized from ethanol, resulting in a received 0,80 g of target compound.

So pl. 148-149aboutWITH

FAB-MS (m/z): 398 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): of 2.56 (3H, s); of 3.80 (3H, s); 7,02 (2H, d, j=8,8 Hz); was 7.08 (1H, DD, j=2.0 a, 8,4 Hz); 7,11 (1H, dt, I=1,6, and 4.4 Hz); 7.18 in-7,27 (1H, m); 7,37 (1H, DD, j=4,8 and 7.6 Hz); EUR 7.57 (2H, d, j=8,8 Hz); 7,71-to 7.84 (2H, m); 8,58 (1H, DD, I=1,6, 4,8 Hz); 9,37 (1H, Shir. C); a 9.60 (1H, Shir. C).

Elemental analysis for C20H19N3O4S:

Calculated: C 60,44, H 4,82, N 10,57

Found: C 60,37, H 4,90, N 10,41

< / BR>
The target compound was obtained by the method described in example 70.

So pl. 199-200aboutC (recrystallized from methanol)

FAB-MS (m/z): 398 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 2,58 (3H, s); 3,81 (3H, s); 7,00-7,07 (3H, m); 7,09-to 7.18 (1H, m); 7,19-7,27 (1H, m); a 7.62 (2H, d, j=8,4 Hz); 7,74-7,80 (1H, m); of 7.82 (1H, d, j=5.6 Hz); 8,80 (1H, d, j=5.6 Hz); 8,87 (1H, s); 9,62 (1H, Shir. C); 10,16 (1H, Shir. C).

P R I m e R 72

N-[2-(4-Methoxybenzenesulfonamide)phenyl]-3-methylethanolamine

[chemical formula 110]

< / BR>
The target compound was obtained by the method described in example 70

So pl. 194-195aboutC (recrystallized from ethanol)

FAB-MS (m/z): 398 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): at 2.36 (3H, s); 3,81 (3H, s); 7.03 is (2H, d, j=8,8 Hz); 7,07 (1H, DD, I=1,6, 8.0 Hz); for 7.12 (1H, dt, I=1,6, 8.0 Hz); 7,20-7,27 (1H, m); of 7.36 (1H, d, j=4,8 Hz); 7,58 (2H, d, j=8,8 Hz); 7,76-7,83 (1H, m); 8,55-8,61 (2H, m); 9,39 (1H, Shir. C); 9,65 (1H, Shir. C).

Elemental analysis for C20H19N3O4S:

Calculated: C 60,44, H 4,82, N 10,57

Found: C 60,29, H a 4.83, N 10,49

P R I m e R 73.

4-[[3-(4-Methoxybenzenesulfonamide)-2-pyridyl] amino] phenyl-D-glucopyranosid

[chemical formula 111]

< / BR>
637 g (0,908 mm) of the compound obtained in example receiving 11, was dissolved in a mixture of 7 ml of 1 n sodium hydroxide and 20 ml erastvere was added 4 ml of 1 n hydrochloric acid, and the resulting mixture was concentrated. To the concentrate was added ethyl acetate and water, and the so formed layer of ethyl acetate was separated, dried, concentrated and was purified by column chromatography on silica gel, resulting in a received 270 mg of the target compound.

1H-NMR (DMCO-d6+D2O) (ppm): 3,15-to 3.33 (4H, m); 3,49 (1H, DD, j=5,6, and 11.6 Hz); 3,70-to 3.73 (4H, s+DD); at 4.75 (1H, d, j=7,6 Hz); of 6.68 (1H, DD, j=4,8, 8.0 Hz); 6,93 (2H, d, j=9,2 Hz); 6,97 (2H, d, j=9,2 Hz); 7.23 percent (1H, DD, I=2,0 7,6 Hz); 7.29 trend (2H, d, j= 9,2 Hz); of 7.60 (2H, d, j=9,2 Hz); of 7.95 (1H, DD, j= 2.0 a, 4,8 Hz).

P R I m e R 74.

4-[[3-(4-Methoxybenzenesulfonamide)-2-pyridyl] amino] phenyl-D-glucopyranosid-uronate

[chemical formula 112]

< / BR>
The target compound was obtained in a manner analogous to the method described in example getting 11 in example 73.

1H-NMR (DMCO-d6+D2O) (ppm): with 3.27 (1H, t, j=8,8 Hz); 3,42 (1H, t, j=8,8 Hz); 3,71 (3H, s); 3,86 (1H, d, j=9.6 Hz); 4.92 in (1H, d, j=7,6 Hz); 6,70 (1H, DD, j= 5,2, 7,6 Hz); make 6.90 (2H, d, j=8,8 Hz); of 6.96 (2H, d, j=8,8 Hz); of 7.25 (1H, DD, j= 1,6 and 7.6 Hz); 7.29 trend (2H, d, j=8,8 Hz); to 7.59 (2H, d, j=8,8 Hz); of 7.95 (1H, DD, I=1,6, 5,2 Hz).

P R I m e R 75.

4-Methoxy-N-[2-[(3,4,5-trimethoxy - nil)amino] -3-pyridyl]benzosulfimide

[chemical formula 113]

< / BR>
The target compound was obtained by way of description; ,72 (1H, DD, j=4,8 and 7.6 Hz); to 6.80 (2H, s+s); 6,98 (2H, d, j=8,8 Hz); from 7.24 (1H, DD, j=1,6 and 7.6 Hz); to 7.59 (2H, d, j=8,8 Hz); 7,81 (1H, Shir. C); 8,00 (1H, DD, I=1,6, 4,8 Hz); for 9.47 (1H, Shir. C).

Elemental analysis for C21H23N3O6S:

Calculated: C 56,62, H 5,20, N 9,43

Found: C 56,42, H 5,22, N 9,14

P R I m e R 76.

4-Methoxy-N-[2-[(2-pyridyl)amino]phenyl]benzosulfimide

[chemical formula 114]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 113-116aboutC (recrystallized from cyclohexane).

FAB-MS (m/z): 356 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 3,70 (3H, s); 6,53-6,59 (1H, m); 6,70 to 6.75 (1H, m); of 6.71 (2H, d, j=8,8 Hz); 6,95 (1H, dt, I=1,2, 8.0 Hz); 7,11 (1H, DD, I= 1,2, 8.0 Hz); 7,14 (1H, dt, I=1,6, 8.0 Hz); 7,41-7,52 (3H, m); to 7.61-7,66 (1H, m); with 8.05 (1H, DD, I=1,2, 4,8 Hz); of 8.06 (1H, Shir. C); 9,59 (1H, Shir. C).

Elemental analysis for C18H17N3O3S:

Calculated: C 60,83, H 4,82, N 11,82

Found: C 61,11, H 4,82, N 11,85

P R I m e R 77.

N-(2-aniline-4-forefeel)-4-methoxy - benzosulfimide

[chemical formula 115]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 173-174aboutC (recrystallized from ethanol).

FAB-MS (m/z): 372 (M+)

1H-NMR (DMCO-d6) (ppm): at 3.69 (3H, s)LASS="ptx2">

Elemental analysis for C19H17FN2O3S:

Calculated: C 61,28, H 4,60, N 7,52

Found: C 61,39, H 4,62, N 7,25

P R I m e R 78.

N-[2-[(4-Course)amino]phenyl]-4-IU - oxybenzoyl the sulfonamide

[chemical formula 116]

< / BR>
The target compound was obtained by the method described in example 1.

FAB-MS (m/z): 388 (M+)

So pl. 127-128aboutC (recrystallized from ethanol)

1H-NMR (DMCO-d6) (ppm): at 3.69 (3H, s); of 6.61 (2H, d, j=8,8 Hz); 6,77 (2H, d, j= 9,2 Hz); 6,88-6,94 (1H, m); 7,07-7,14 (4H, m), 7,18 (1H, DD, I= 1,2, 8.0 Hz); of 7.36 (1H, Shir. C); 7,47 (2H, d, j=9,2 Hz); 9.28 are (1H, Shir. C).

Elemental analysis for C19H17ClN2O3S:

Calculated: 58,68, N TO 4.41, N 7,20

Found: C 58,85, H 4,39, N? 7.04 baby mortality

P R I m e R 79.

N-[2-[(3-Hydroxyphenyl)amino]phenyl]-4-methoxybenzenesulfonamide

[chemical formula 117]

< / BR>
The target compound was obtained by a method similar to that described in example 1.

So pl. 165-166aboutC (recrystallized from ethanol)

FAB-MS (m/z): 370 (M+)

1H-NMR (DMCO-d6) (ppm): 3,71 (3H, s); 6,12-of 6.17 (2H, s); to 6.19-6,24 (1H, m); 6,79-6,86 (3H, m); 6,91 (1H, t, j=8,4 Hz); 7,07 (1H, dt, I=1,2, 8.0 Hz); was 7.08 (1H, DD, I=1,2, 8.0 Hz); 7,13 (1H, DD, I=1,2, 8.0 Hz); 7,14 (1H, Shir. C); 7,52 (2H, d, j=8,8 Hz); 9,16 (1H, s), 9.28 are (1H, Shir. C).

Cell battery (included) is

P R I m e R 80.

4-Benzyloxy-N-[2-(4-methoxybenzyl - ltname)phenyl]-benzamide

[chemical formula 118]

< / BR>
The target compound was obtained by the method described in example 70.

So pl. 148-149aboutC (recrystallized from ethanol)

FAB-MS (m/z): 489 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 3,74 (3H, s); 5,23 (2H, s); 6.89 in (2H, d, j=8,8 Hz); 7,07 (1H, DD, j=2,0, 8.0 Hz); 7,10 (1H, dt, I=1,2, 8.0 Hz); 7,17 (2H, d, j=8,8 Hz); 7.23 percent (1H, dt. I=to 2.0, 8.0 Hz); 7,33-7,39 (1H, m); 7,42 (2H, t, j= 7,6 Hz); 7,47-7,52 (4H, m); 7,74 (1H, DD, I=1,2, 8.0 Hz); 7,81 (2H, d, j= 8,8 Hz); 9,44 (1H, Shir. C); for 9.47 (1H, Shir. C).

Elemental analysis for C27H24N2O5S:

Calculated: C 66,38, H 4,95, N 5,73

Found: C 66,34, H 4,92, N 5,73

P R I m e R 81.

4-Hydroxy-N-[2-(4-methoxybenzoyl - fanmigo)phenyl]benzamide

[chemical formula 119]

< / BR>
The target compound was obtained by catalytic reduction of the compound obtained in example 80, in accordance with standard procedure.

So pl. 205-207aboutC (recrystallized from ethyl acetate)

FAB-MS (m/z): 399 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 3,76 (3H, s); 6.89 in (2H, d, j=8,8 Hz); 6,91 (2H, d, j= 8,8 Hz);? 7.04 baby mortality (1H, DD, I=1,6, 8.0 Hz); to 7.09 (1H, dt, I=1,6, 8.0 Hz); 7,20-of 7.25 (1H, m); 7,50 (2H, d, j=8,8 Hz); 7.68 per-7,76 (3H, m); 9,38 (1H, s); for 9.47 (1H, s); and 10.20 (1H, s). the Deno: C 60,38, H 4,58, N 6,75

P R I m e R 82.

4-Fluorescent-N-[2-(4-methoxybenzylthio - amido)phenyl]benzamide

[chemical formula 120]

< / BR>
The target compound was obtained by the method described in example 70.

So pl. 169-170aboutC (recrystallized from ethanol)

FAB-MS (m/z): 401 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 3,75 (3H, s); make 6.90 (2H, d); 7,07-7,16 (2H, m); 7,19-7,26 (1H, m); 7,39 (2H, t, j=8,8 Hz); 7,50 (2H, d, j=8,8 Hz); 7,66-7,73 (1H, m); to $ 7.91 (2H, DD, j=5,6, 8,8 Hz); 9,38 (1H, Shir. C); 9,54 (1H, Shir. C).

Elemental analysis for C20H17FN2O4S:

Calculated: C 59,99; H 4,28; N 7,00

Found: C 60,00; H or 4.31; N 6,70

P R I m e R 83.

3-Hydroxy-N-[2-(4-methoxybenzoyl - fanmigo)phenyl]benzamide

[chemical formula 121]

< / BR>
The target compound was obtained by the method described in example 81.

So pl. 191-192aboutC (recrystallized from ethanol)

FAB-MS (m/z): 399 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): of 3.77 (3H, s); 6,92 (2H, d, j=8,8 Hz); 6,99-7,06 (2H, m); to 7.09 (1H, DM, I=1,6, 8.0 Hz); 7,20-7,27 (3H, m); 7,34 (1H, t, j= 8.0 Hz); 7,51 (2H, t, j=8,8 Hz); 7,75-7,81 (1H, m); 9,46 (1H, s); 9,51 (1H, C); 9,81 (1H, s).

Elemental analysis for C20H18N2O5S:

Calculated: C 60,29; H 4,55; N 7,03

Found: C 60,41; H 4,55; N OF 6.71

P R I m e R 84.

N-[2-(4-Methoxy what the group was received by way described in example 70.

So pl. 136-137aboutC (recrystallized from ethanol) FAB-MS (m/z): 389 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 3,75 (3H, s); 6,85 (2H, d, j=8,8 Hz); 7,05-7,13 (2H, m); 7,17-7,26 (2H, m); 7,49 (2H, d, j=8,8 Hz); 7,60-of 7.70 (1H, m); to 7.77 (1H, DD, I=1,6, 4.0 Hz); 7,87 (1H, DD, I=1,6, 5,2 Hz); 9,50 (2H, Shir. C).

Elemental analysis for C18H16N2O4S:

Calculated: C 55,65; H 4,15; N 7,21

Found: C 55,80; H 4,27; N 7,24

P R I m e R 85.

N-[2-(4-Methoxybenzenesulfonamide)phenyl]-2-furancarboxylic

[chemical formula 123]

< / BR>
The target compound was obtained by the method described in example 70.

So pl. 158-159aboutC (recrystallized from ethanol)

FAB-MS (m/z): 373 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 3,76 (3H, s); of 6.73 (1H, DD, I=1,6, 3.6 Hz); 6,91 (2H, d, j=8,8 Hz); 6,98 (1H, DD, j=8.0 Hz); was 7.08 (1H, dt, I=1,6, 8.0 Hz); 7,21 (1H, DD, j=0,8, 3.6 Hz); from 7.24 (1H, dt, I=1,6, 8.0 Hz); 7,53 (2H, d, I= 8,8 Hz); to 7.84 (1H, DD, I=1,6, 8.0 Hz); 7,99 (1H, DD, j=0,8 and 1,6 Hz); 9,42 (1H, Shir. C); 9,62 (1H, Shir. C).

Elemental analysis for C18H16N2O5S:

Calculated: 58,05; H 4,33; N 7,52

Found: 58,08; H 4,39; N 7,44

P R I m e R 86.

N-[2-(4-Methoxybenzenesulfonamide)phenyl]-2-pyridinecarboxamide

[chemical formula 124]

< / BR>
The target compound was obtained JV
FAB-MS (m/z): 384 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 3,75 (3H, s); PC 6.82 (1H, DD, I=1,6, 8.0 Hz); 6,92 (2H, d, j=8,8 Hz); 7.03 is (1H, dt, I=1,6, 8.0 Hz); 7,30 (1H, dt, I=1,6, 8.0 Hz); EUR 7.57 (2H, d, j=8,8 Hz); of 7.70 (1H, TD, I=1,6, of 4.8 and 7.6 Hz); 8,08 (1H, dt, I= a 1.6 and 7.6 Hz); 8,12-8,17 (1H, m); 8,24 (1H, DD, j=1,6 and 7.6 Hz); 8,77 (1H, DD, I=1,6, 4,8 Hz); 9,73 (1H, Shir. C); 10,67 (1H, Shir. C).

Elemental analysis for C19H17N3O4S:

Calculated: 59,52; H 4,47; N 10,96

Found: C 59,73; H of 4.54; N 10,92

P R I m e R 87.

N-[2-(4-Methoxybenzenesulfonamide)phenyl]nicotime

[chemical formula 125]

< / BR>
The target compound was obtained by the method described in example 70.

So pl. 179-180aboutC (recrystallized from ethanol)

FAB-MS (m/z): 384 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 3,74 (3H, s); 6.89 in (2H, d, j=8,8 Hz); 7,12-7,19 (2H, m); 7,19-7,27 (1H, m); 7,51 (2H, d, j=8,8 Hz); to 7.59 (1H, DD, j= 4,8, 8.0 Hz); 7,63-7,71 (1H, m), 8,17 (1H, DD, I=1,2, 8.0 Hz); 8,79 (1H, DD, I=1,2, 4,8 Hz); 8,99 (1H, d, j=1.2 Hz); 9,49 (1H, Shir. C); 9,68 (1H, Shir. C. ).

Elemental analysis for C19H17N3O4S:

Calculated: C 59,52; H 4,47; N 10,96

Found: C 59,61; H of 4.57; N 10,84

P R I m e R 88.

N-[2-(4-Methoxybenzenesulfonamide)phenyl]isonicotinamide

[chemical formula 126]

< / BR>
The target compound was obtained by the method described in example 70.

6) (ppm): 3,75 (3H, s); make 6.90 (2H, d, j=8,8 Hz); 7,11-7,27 (3H, m); 7,53 (2H, d, j=8,8 Hz); of 7.64-7,71 (1H, t); of 7.75 (2H, d, j=4,8 Hz); 8,81 (2H, d, j=4,8 Hz); 9,52 (1H, Shir. C); 9,73 (1H, Shir. C).

Elemental analysis for C19H17N3O4S:

Calculated: C 59,52; H 4,47; N 10,96

Found: C 59,59; H to 4.52; N 10,96

P R I m e R 89.

4-Fluorescent-N-[2-(4-methoxybenzylthio - amido)-6-were] benzamide

[chemical formula 127]

< / BR>
The target compound was obtained by the method described in example 70.

So pl. 204-206aboutC (recrystallized from ethanol)

FAB-MS (m/z): 415 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 2,10 (3H, s); of 3.80 (3H, s); 6,97 (2H, d, j=8,8 Hz); 7,00 for 7.12 (3H, m); 7,37 (2H, t, j=8,8 Hz); the 7.65 (2H, d, j=8,8 Hz); 8,03 (2H, DD, j=5,6, 8,8 Hz); 9,46 (1H, Shir. C); 9,48 (1H, Shir. C).

Elemental analysis for C21H19FN2O4S:

Calculated: C 60,86; H to 4.62; N 6,76

Found: C 60,74; H 4,56; N 6,65

P R I m e R 90.

N-[2-(4-methoxybenzenesulfonamide)-6-were]nicotinamide

[chemical formula 128]

< / BR>
Target state was obtained by the method described in example 70.

So pl. 207-209aboutC (recrystallized from ethanol)

FAB-MS (m/z): 398 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 2,11 (3H, s); with 3.79 (3H, s); 6,98 (2H, d, j=8,8 Hz); 7,02 (1H, DD, j=1,6 and 7.6 Hz); 7,05-7,14 (who, Shir. C).

Elemental analysis for C20H19N3O4S:

Calculated: C 60,44; H 4,82; N 10,57

Found: C 60,55; H 4,90; N 10,53

P R I m e R 91.

N-[2-(4-Methoxybenzenesulfonamide)-6-were]isonicotinamide

[chemical formula 129]

< / BR>
The target compound was obtained by the method described in example 70.

So pl. 213-217aboutC (recrystallized from ethanol)

FAB-MS (m/z): 398 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 2,10 (3H, s); of 3.80 (3H, s); 6,99 (2H, d, j=8,8 Hz); 7,02 (1H, DD, j=1,6 and 7.6 Hz);? 7.04 baby mortality-7,14 (2H, m); to 7.67 (2H, d, j=8,8 Hz); 7,87 (2H, DD, I=1,6, and 8.4 Hz); 8,80 (2H, DD, I=1,6, and 8.4 Hz); of 9.56 (1H, Shir. C); at 9.53 (1H, Shir. C).

Elemental analysis for C20H19N3O4S:

Calculated: C 60,44; H 4,82; N 10,57

Found: C 60,60; H is 4.85; N 10,53

P R I m e R 92. N-[2-(4-methoxybenzenesulfonamide)-6-were]-2-pyridinecarboxamide

[chemical formula 130]

< / BR>
The target compound was obtained by the method described in example 70.

So pl. 180-182aboutC (recrystallized from ethanol)

FAB-MS (m/z): 398 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 2,12 (3H, s); of 3.78 (3H, s); make 6.90 (2H, d, j=8,8 Hz); 6,93 (1H, t, j=4,8 Hz); 7,11 (2H, d, j=4,8 Hz); rate of 7.54 (2H, d, j=8,8 Hz); the 7.65 7,72 (1H, m); 8,03-8,08 (2H, m); is 8.75 (1H, DD, j=1,2, 5,2 Hz); at 9.53 (1H, Shir. C); 10,11 (1H, Shir. C).

H 4,92; N 10,45

P R I m e R 93.

N-[2-(4-Methoxybenzenesulfonamide)phenyl]-2-nitrobenzamide

[chemical formula 131]

< / BR>
The target compound was obtained by the method described in example 70.

So pl. 168-170aboutC (recrystallized from ethanol)

FAB-MS (m/z): 428 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): of 3.80 (3H, s); 7,05 (2H, d, j=8,8 Hz); 7,07-7,16 (2H, m); 7,19-7,26 (1H, m); a 7.62 (2H, d, j=8,8 Hz); 7,66 (1H, d, j=8.0 Hz); 7,73 (1H, d, j=8.0 Hz); 7,79 (1H, t, j=8.0 Hz); a 7.92 (1H, t, I=8.0 Hz); 8,16 (1H, d, j=8.0 Hz); 9,23 (1H, Shir. with); to 9.93 (1H, Shir. C).

Elemental analysis for C20H17N3O6S:

Calculated: C 56,20; H 4,01; N 9,83

Found: C 56,21; H of 4.05; N 9,77

P R I m e R 94.

2-Chloro-4-fluorescent-N-[2-(4-methoxybenzo - sulphonamido)phenyl]-benzamide

[chemical formula 132]

< / BR>
The target compound was obtained by the method described in example 70.

So pl. 160-162aboutC (recrystallized from ethanol)

FAB-MS (m/z): 435 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 3,81 (3H, s); 6,97-to 7.18 (4H, m); 7,19-7,28 (1H, m); 7,34-7,44 (1H, m); 7,51-to 7.64 (4H, m); 6,74-of 7.82 (1H, m); was 9.33 (1H, Shir. C); RS 9.69 (1H, s).

Elemental analysis for C20H16ClN2O4S:

Calculated: C 55,24; H 3,71; N 6,44

Found: C to 55.42; H 3,90; N 6,20

P R I m e R 95.

N-[2-(4-Methoxybenzyl, described in example 70.

So pl. 129-130aboutC (recrystallized from ethanol)

FAB-MS (m/z): 397 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): of 2.38 (3H, s); 3,81 (3H, s); 7.03 is (2H, d, j=8,8 Hz); 7,07 (1H, DD, j=2,0, 8.0 Hz); 7,10 (1H, DD, I=1,2, 8.0 Hz); 7,19-7,27 (1H, m); 7,27-7,39 (3H, m); 7,42 (1H, dt, I=2,0, 7,2 Hz); 7,56 (2H, d, I=8,8 Hz); 7,80-7,87 (1H, m); 9,40 (1H, Shir. C); 9,46 (1H, Shir. C).

Elemental analysis for C21H20N2O4S:

Calculated: C 63,62; H 5,09; N 7,07

Found: C 63,64; H 5,09; N 7,03

P R I m e R 96.

2-Chloro-N-[2-(4-methoxybenzylthio - amido)phenyl]nicotinamide

[chemical formula 134]

< / BR>
The target compound was obtained by the method described in example 70.

So pl. 133-135aboutC (recrystallized from ethanol)

FAB-MS (m/z): 418 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 3,81 (3H, s);? 7.04 baby mortality (2H, d, j=8,8 Hz); 7,07-to 7.15 (2H, m); 7.18 in-7,22 (1H, m), 7,60 (2H, d, j=8,8 Hz); to 7.61 (1H, DD, j= 4,8 and 7.6 Hz); for 7.78 (1H, d, j=7,6 Hz); 7,98 (1H, DD, j=2.0 a, 7,6 Hz); 8,56 (1H, DD, I=2,0, 4,8 Hz); 9,29 (1H, Shir. C); 9,87 (1H, s).

Elemental analysis for C19H16ClN3O4S:

Calculated: C 54,61; H 3,86; N 10,06

Found: C 54,71; H a 3.87; N 9,90

P R I m e R 97.

4-Fluorescent-N-[2-(4-methoxybenzylthio - amido)phenyl]sensational

[chemical formula 135]

< / BR>
The mixture 549 mg (1,371 mm) sedimentirutaya the residue was purified by column chromatography on silica gel, resulting received 506 mg of the target compound.

So pl. 155-156aboutC (after recrystallization from n-butanol)

FAB-MS (m/z): 417 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): of 3.80 (3H, s); 7,02 (2H, d, j=8,8 Hz); 7,10-of 7.25 (3H, m), 7,33 (2H, t, j=8,8 Hz); 7,47-7,58 (1H, m); 7,63 (2H, d, j=8,8 Hz); 7,98 (2H, DD, j=5,6, 8,8 Hz); of 9.45 (1H, width); 11,13 (1H, Shir).

Elemental analysis for C20H17FN2O3S2:

Calculated: C 57,68; H 4,11; N, 6.73 X

Found: C 57,63; H 4,12; N 6,58

P R I m e R 98.

N-[5-fluorescent-2-(4-methoxybenzylthio-amido)phenyl]benzamide

[chemical formula 136]

< / BR>
The target compound was obtained by the method described in example 70.

So pl. 153-154aboutC (after recrystallization from ethanol)

FAB-MS (m/z): 401 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 3,75 (3H, s); to 6.88 (2H, d, j=8,8 Hz);6,94 (1H, dt, j= 3.2, and an 8.8 Hz); 7,00 (1H, DD, j=6,0, 8,8 Hz); 7,47 (2H, d, j=8,8 Hz); at 7.55 (2H, t, j=7,6 Hz); to 7.59-7,66 (1H, m); 7,74-7,83 (3H, m); to 9.45 (1H, Shir. C); of 9.55 (1H, Shir. C).

Elemental analysis for C20H17FN2O4S:

Calculated: C 59,55; H 4,28; N 7,00

Found: C 59,97; H 4,32; N 6,79

P R I m e R 99.

4-Fluorescent-N-[2-(4-nitrobenzenesulfonyl - Mido)phenyl]benzamide

[chemical formula 137]

< / BR>
The target compound was obtained from the compound, is cristallization from ethyl acetate)

FAB-MS (m/z): 416 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 7,21 (1H, dt, I=1,6, 8.0 Hz); of 7.25 (1H, DD, j= 2,0, 8.0 Hz); 7,30 (1H, dt, I=2,0, 8.0 Hz); to 7.35 (2H, t, j=8,8 Hz); 7,55-of 7.60 (1H, m); 7,76 (2H, d, j=8,8 Hz); 7,83 (2H, DD, j=5,6, 8,8 Hz); by 8.22 (2H, d, I=8,8 Hz); 9,42 (1H, s); of 9.89 (1H, s).

Elemental analysis for C19H19FN3O5S:

Calculated: C 54,94; H 3,40; N 10,12

Found: C 54,90; H 3,36; N TO 9.93

P R I m e R 100.

2-Chloro-6-methyl-N-[2-(4-methoxybenzo - sulphonamido)phenyl] isonicotinamide

[chemical formula 138]

< / BR>
The target compound was obtained by the method described in example 1.

So pl. 150-151aboutC (after recrystallization from ethanol)

FAB-MS (m/z): 432 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 2,58 (3H, s); 3,76 (3H, s); make 6.90 (2H, d, j=8,8 Hz); 7,15-7,26 (3H, m), 7,52 (2H, d, j=8,8 Hz); 7,54-7,63 (3H, m); 9,44 (1H, Shir. C); 9,73 (1H, Shir. C).

Elemental analysis for C20H18ClN3O4S:

Calculated: C 55,62; H 4,20; N 9,73

Found: C 55,80; H 4.26 deaths; N 9,75

P R I m e R 101.

N-[2-(4-methoxybenzenesulfonamide)phenyl]ndimethylacetamide

[chemical formula 139]

< / BR>
The target compound was obtained by the method described in example 70.

So pl. 160-161aboutC (recrystallized from ethanol)

FAB-MS (m/z): 321 ([M+H]+)

1H-NMR (DMCO-d615H16N2O4S:

Calculated: C 56,24; H to 5.03; N 8,75

Found: C, 56.26 vertical; H to 5.03; N 8,72

P R I m e R 102.

N-[2-(4-Methoxybenzenesulfonamide)phenyl]formamide

[chemical formula 140]

< / BR>
The target compound was obtained by the method described in example 70.

So pl. 143-144aboutC (recrystallized from ethanol)

FAB-MS (m/z): 307 ([M+H]+)

Elemental analysis for C14H14N2O4S:

Calculated: C 54,89; H br4.61; N 9,14

Found: C 55,05; H 4,65; N IS 9.09

P R I m e R 103.

N-[2-[(Etoxycarbonyl)amino]phenyl]-4-methoxybenzenesulfonamide

[chemical formula 141]

< / BR>
The target compound was obtained by the method described in example 70.

So pl. 118-119aboutC (recrystallized from ethanol)

FAB-MS (m/z): 351 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 1,22 (3H, t, j=7.2 Hz); with 3.79 (3H, s); a 4.03 (2H, sq I=7,2 Hz); 6,98-7,03 (4H, m); 7,17 (1H, t, j=8.0 Hz); 7,52 (2H, d, j=8,8 Hz); EUR 7.57 (1H, d, j=8.0 Hz); 8,43 (1H, s); a 9.35 (1H, s).

Elemental analysis for C16H18N2O5S:

Calculated: C 54,84; H 5,18; N 7,99

Found: C 54,78; H 5,19; N 7,86

P R I m e R 104.

N-[2-[(Ethylaminomethyl)amino]Hairdryer-yl]-4-methoxybenzenesulfonamide

[chemical formula 142]

< / BR>
The target connection processing of the product in a standard way.

So pl. 152-154aboutC (recrystallized from ethanol)

FAB-MS (m/z): 350 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 1,08 (3H, t, j=7.2 Hz); 3,10 (2H, DQC. I=5,6, 7,2 Hz); 3,82 (3H, s); of 6.61 (1H, DD, I=1,6, 8.0 Hz); 6,77 (1H, dt, I=1,2, 8.0 Hz); 6.89 in (1H, t, j=5.6 Hz);? 7.04 baby mortality (2H, d, j=8,8 Hz); 7,05 for 7.12 (1H, m); EUR 7.57 (2H, d, j= 8,8 Hz); for 7.78 (1H, DD, j=1,2, and 8.4 Hz); 7,94 (1H, s); 9,41 (1H, s).

Elemental analysis for C16H19N3O4S:

Calculated: 55,00; H 5,48; N A 12.03

Found: C 55,08; H vs. 5.47; N 11,88

P R I m e R 105.

N-[3-(4-Methoxybenzenesulfonamide)-2-pyridyl]-2-methylbenzamide

[chemical formula 143]

< / BR>
The target compound was obtained by the method described in example 70.

So pl. 160-162aboutC (recrystallized from ethanol)

FAB-MS (m/z): 398 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): is 2.37 (3H, s); 3,81 (3H, s); 7,05 (2H, d, j=8,8 Hz); 7,22-of 7.23 (4H, m); of 7.36-the 7.43 (1H, m); to 7.59 (2H, d, j=8,8 Hz); 7,71 (1H, DD, I= 1,6, 8.0 Hz); of 8.25 (1H, DD, I=1,6, 4,8 Hz); 9,24 (1H, Shir. C); of 10.47 (1H, Shir. C).

Elemental analysis for C20H19N3O4S:

Calculated: C 60,44; H 4,82; N 10,57

Found: C 60,53; H 4,84; N 10,67

P R I m e R 106.

N-[2-(4-Aminobenzenesulfonamide)Fe - Neil]-4-foraminated

[chemical formula 144]

< / BR>
The target compound was obtained by reconnection, polichno from ethanol)

FAB-MS (m/z): 386 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 5,98 (2H, Shir. C); 6,45 (2H, d, j=8,8 Hz); 7,05 (1H, DD, I=1,6, 8.0 Hz); to 7.09 (1H, dt, I=1,6, 8.0 Hz); 7,20 (1H, dt, I= 1,6, 8.0 Hz); 7.23 percent (2H, d, j=8,8 Hz); 7,39 (2H, t, j=8,8 Hz); 7,74-7,80 (1H, m); to 7.93 (2H, DD, j=5,6, 8,8 Hz); 9,20 (1H, Shir. C); 9,63 (1H, Shir. C).

Elemental analysis for C19H16FN3O3S:

Calculated: C 59,21; H 4,18; N 10,90

Found: C 59,36; H 4,21; N 10,80

P R I m e R 107.

N-[2-(4-Chlorobenzenesulfonamide)Fe-Neil]benzamide

[chemical formula 145]

< / BR>
The target compound was obtained by the method described in example 70.

So pl. 191-192aboutC (recrystallized from ethanol)

FAB-MS (m/z): 387 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 7,13-7,20 (2H, m); 7.24 to 7,30 (1H, m); 7,42 (2H, d, j=8,8 Hz); rate of 7.54 (2H, d, j=8,8 Hz); at 7.55 (2H, t, j=8,8 Hz); 7,60-7,66 (1H, m); 7.68 per-7,72 (1H, m); 7,78-7,83 (2H, m); 9,52 (1H, s); 9,71 (1H, s).

Elemental analysis for C19H15ClN2O3S:

Calculated: 58,99; H 3,91; N 7,24

Found: C 59,25; H was 4.02; N 7,29

P R I m e R 108.

N-[2-(3,4-Dimethoxybenzenesulfonamide - up)phenyl]benzamide

[chemical formula 146]

< / BR>
The target compound was obtained by the method described in example 70.

So pl. 183-184aboutC (recrystallized from ethanol)

FAB-MS (m/z): 413 ([M+H]+)

23-7,29 (1H, m); 7,54 (2H, t, j=7,6 Hz); to 7.59 - the 7.65 (1H, m); 7,71-7,76 (1H, m); 7,76-of 7.82 (2H, m); 9,43 (1H, Shir. C); at 9.53 (1H, Shir. C).

Elemental analysis for C21H20N2O5S:

Calculated: C 61,15; H 4,89; N 6,79

Found: C 61,16; H 4,90; N 6,82

P R I m e R 109.

N-[2-(4-Methoxybenzenesulfonamide)phenyl]benzamide

[chemical formula 147]

< / BR>
The target compound was obtained by the method described in example 70.

So pl. 167-168aboutC (recrystallized from ethanol)

FAB-MS (m/z): 383 ([M+H]+)

1H-NMR (DMCO-d6) (ppm): 3,75 (3H, s); 6,91 (2H, d, j=8,8 Hz); was 7.08 (1H, DD, I=1,6, 8.0 Hz); for 7.12 (1H, dt, I=1,6, 8.0 Hz); from 7.24 (1H, dt, I=1,6, 8.0 Hz); 7,51 (2H, d, j=8,8 Hz); 7,52-to 7.59 (2H, m); 7,60-7,66 (1H, m); 7,76 (1H, DD, I= 1,6, 8.0 Hz); 7,81-7,86 (2H, m); 9,50 (1H, Shir. C); of 9.55 (1H, Shir. C).

Elemental analysis for C20H18N2O4S:

Calculated: C 62,81; H 4,74; N 7,33

Found: C 63,06; H of 4.77; N 7,32

P R I m e R 110.

4 Ethoxy-N-[2-((4-hydroxyphenyl)AMI) -3-pyridyl]benzosulfimide

< / BR>
Received target connection.

So pl. 194-195aboutC (recrystallized from ethanol)

FAB-MS (m/z): 386 ([M+H]+)

Elemental analysis for C19H19N3O3S:

Calculated: C 59,21; H equal to 4.97; N 10,90

Found: C 59,12; H is 4.93; N 10,66

1H-NMR (DMCO-d6) (ppm): 1,7,6 Hz); at 7.55 (1H, Shir. C); 7,56 (2H, d, j=9,2 Hz); 7,87 (1H, DD, I=1,6, 4,8 Hz); 8,97 (1H, s); 9,41 (1H, Shir. C).

1. DERIVATIVES SULFONAMIDA General formula

< / BR>
where R1lower alkyl, lower alkoxy, amino;

R2hydrogen, lower alkyl;

R3and R4different and each represents halogen, lower alkoxy - or both hydrogen;

A denotes the N Ilin-;

B N or

where R5hydrogen, lower alkyl;

a group of the formula

< / BR>
where Q is oxygen or sulfur, R6hydrogen, lower alkyl, lower alkoxy, lower alkylamino, 2-furyl, phenyl which may be substituted by lower alkyl, hydroxy, halogen, or R6pyridyl which may be substituted by lower alkyl, halogen; pyridyl, pyrimidinyl or phenyl which may be substituted by a lower alkyloxy, hydroxyl, lower alkyl, halogen, (lower)alkyloxy(lower)alkyloxy, phenylcarbamoyloxy, phosphoryloxy, glucopyranosyloxy, lower allyloxycarbonyl, dimethylaminocarbonylmethyl, aminoacetate, aminobenzoate, phenoxy, or their pharmacologically acceptable salts, except when (a) R1lower alkyl, amino, R2hydrogen, and In group-CH-; phenyl which may be substituted by hydroxyl, halogen, NISS is anabantidae, b) R2lower alkyl, In kaidyn-,

e group of the formula

< / BR>
where R6lower alkyl, lower alkylamino, or phenyl which may be substituted by lower alkoxy, hydroxyl, lower alkyl, halogen, phenylcarbamoyloxy, lower allyloxycarbonyl, dimetilaminoflavonola, aminobenzoylamino,

or their pharmacologically acceptable salts.

2. Derivatives sulfonamida under item 1, representing a compound of General formula

< / BR>
< / BR>
< / BR>
or a pharmacologically acceptable salt.

Priority signs

20.08.90 when R1lower alkyl, lower alkyloxy, amino, R2hydrogen, lower alkyl, R3and R4both hydrogen. A CH-B N-, phenyl which may be substituted by lower alkoxy, lower alkyl, hydroxy, halogen, lower alkylacrylate alkyloxyaryl or pyridyl, or their pharmacologically acceptable salts.

05.03.91 when A N-B

< / BR>
where R5hydrogen, R3and R4identical or different halogen, lower alkoxy, phenyl substituted lower alkoxycarbonyl, phenoxy, dimethylaminocarbonylmethyl, phenylcarbamoyloxy, aminoacetate, aminobenzoate, phosphoryloxy or pyrimidinyl.

27.05.91 at e group of the formula

< / BR>
where R5lower alkyl.

 

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FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to biologically active compounds. Agent represents 3,6-dioxocyclohexa-1,4-diene-1,2,4,5-tetrasulfonate sodium. The new agent elicits antioxidant properties and therefore it can be used in food industry, in pharmaceutical compositions and cosmetic products. Also, the new agent elicits antiviral activity owing to it can be used as both the independent medicinal agent and in compositions with other preparations used for treatment of viral infections.

EFFECT: expanded assortment of medicinal agents and antioxidants, realization of indicated prescription.

1 tbl, 8 dwg

FIELD: organic chemistry, pharmacy.

SUBSTANCE: invention relates to new biphenylsulfonylcyanamides of the formula (I): wherein R1 means: 1. (C1-C8)-alkyl; 4. -CnH2n-nn-Y wherein nn = 0 or 2 and n = 0-4, and n is not 0 or 1 if nn = 2; 5. CnH2n-nn-Y wherein nn = 0 or 2 and n = 1-4, and n is not 1 if nn = 2, and 1 hydrogen atom in bivalent residue CnH2n-nn is substituted with amino-group or NR(22)R(23); R2 means: 2. (C1-C)-alkyl; 4. (C2-C12)-alkenyl; 5. (C2-C8)-alkynyl; 6. -CnH2n-nn-Z wherein nn = 0 or 2; n = 0-4, and n is not or 1 if nn = 2; 7. -CnH2n-nn-Z wherein nn = 0 or 2; n = 1-4, and n is not 1 if nn = 2, and 1 hydrogen atom in bivalent residue CnH2n-nn is substituted with a residue taken among a series: 1. phenyl; 3. NR(22)R(23); 5. COOR(16); R3 and R4 mean hydrogen atom; R5, R6 and R7 mean independently of one another hydrogen atom (H), (C1-C8)-alkyl; SO2-(C1-C4)-alkyl, F, Cl, Br, J, OR(10) wherein R(10) means hydrogen atom, (C1-C4)-alkyl that is substituted if necessary with methoxy- or ethoxy-group; R(9) means OR(13) wherein R(13) means hydrogen atom, H,(C1-C8)-alkyl;X means carbonyl group, -CO-CO- or sulfonyl group; Y and Z mean independently of one another: 1. phenyl, 1-naphthyl, 2-naphthyl; 2. one of residues determined in cl. 1 substituted with 1-5 similar or different residues taken among a series: phenyl, F, Cl, Br, J, CF3, SOqR(18), OR(16), NR(19)R(20), -CN, NO2, COR(9), or two residues form methylenedioxy-group; 3. furyl, thienyl, pyridyl, benzimidazolyl, indolyl, benzothiophenyl, dihydroquinazolinyl; 5. (C3-C10)-cycloalkyl wherein cyclopropyl, cyclopentyl, cyclohexyl and indalyl are preferable; 6. one of residues determined in cl. 5 substituted with phenyl; R(16) means: 1. hydrogen atom; 2. (C1-C4)-alkyl; 3. (C1-C4)-alkyl substituted with (C1-C4)-alkoxy-group; R(19) and R(20) mean independently: hydrogen atom (H), (C1-C4)-alkyl; R(22) and R(23) mean independently of one another hydrogen atom (H) or CO-OR(24) wherein R924) means -CnH2n-phenyl wherein n = 1-4; q = 2; and their physiologically acceptable salts. Compound of the formula (I) inhibit sodium-dependent chloride-bicarbonate exchange "NCBE".

EFFECT: improved preparing method, valuable medicinal properties of compounds.

4 cl, 2 tbl, 568 ex

FIELD: pharmaceutical industry, medicine.

SUBSTANCE: invention relates to new compounds of formula

,

wherein A and B are independently CH or CR3; X is C=O or (CR4aR4b)m, (m = 1 or 2); Y is S(O)n-R2 (n = 1 or 2), S(O)n-NR2R2, or S(O)n-OR2; N1 and N2 are nitrogen atoms; Q and R1 are independently 1) optionally substituted C1-C10-alkyl; 2) optionally substituted aralkyl containing C6-C10-aryl, attached to C1-C10-alkyl; 3) optionally substituted aralkenyl containing C5-C10-aryl, attached to C1-C10-alkenyl; 4) optionally substituted C6-C10-aryl; 5) optionally substituted aryl, containing 5-10 ring atoms, selected from carbon and sulfur; each R2 and R3 are hydrogen; R4a, R4b, R5, and R6, are independently hydrogen; R2 and R3 are independently hydrogen or C1-C6-alkyl; as well as acid and base additive salts thereof. Also disclosed are method for production of claimed compounds, pharmaceutical composition inhibiting serine protease enzymes and therapeutic method based thereon.

EFFECT: new compounds and pharmaceutical composition for thrombosis preventing or abnormal thrombosis treatment.

11 cl, 7 tbl, 15 ex

FIELD: medicine, surgery.

SUBSTANCE: on should perform continuous washing patient's foot for several days due to placing it into hermetically sealed reservoir with antiseptic followed by vacuum evaporation at rarefaction being 0.2-0.4 kgf/sq. cm, moreover, procedures should be alternated at periodicity of 3-4 h. The present innovation enables to accelerate wound purification and increase regenerative activity of plantar tissues due to suppressing activity of the agent of purulent-necrotic process, activation of local immunity of affected tissues and restoration of microcirculation and oxygenation of these tissues.

EFFECT: higher efficiency of therapy.

1 ex

FIELD: organic chemistry, medicine, pharmacy.

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EFFECT: valuable medicinal properties of compounds.

13 cl, 2 dwg, 2 tbl, 18 ex

FIELD: organic chemistry, medicine, pharmacology, biochemistry, pharmacy.

SUBSTANCE: invention proposes poly-(para-dihydroxy-para-phenylene)-thiosulfoacid sodium salt of the general formula:

wherein n = 2-6 as a substance regulating cell metabolism and eliciting anti-hypoxic properties. Also, invention proposes a pharmaceutical composition based on the indicated compound. Applying the compound provides the expressed anti-hypoxic effect. Invention can be used in cosmetology and food industry and relates to preparations regulating metabolism in separated cells and their consortium in biological tissues.

EFFECT: valuable biological and medicinal properties of compound.

4 cl, 10 tbl, 4 dwg, 6 ex

FIELD: medicine, transplantology.

SUBSTANCE: method involves applying (R)-ibuprofen methanesulfonamide and its nontoxic salts for preparing medicinal agents used for prophylaxis or treatment of ischemic, reprefusion and functional damages of transplanted organs. Invention provides prophylaxis such complications as delayed function of transplant arising in transplantation of organs.

EFFECT: valuable medicinal properties of medicinal agent.

5 cl, 5 tbl, 1 dwg, 2 ex

FIELD: medicine, neurology.

SUBSTANCE: the method deals with detecting an interferon status followed by medicinal therapy. Moreover, additionally one should determine patient's body area, and at observed degree I of interferon system suppression it is necessary to prescribe "Antilympholin Kz" preparation as medicinal therapy intravenously by drops at course dosage being (0.5-0.6)g x S, where S - patient's body area, every other day, and thioctacide preparation at the dosage of 300-600 mg intravenously by drops daily at a 6-8-d-long course. In case of degrees II and III of interferon system suppression one should prescribe "Antilympholin Kz" at course dosage being 0.4-0.5 g/sq. m and 0.3 -.4 g/sq. m, as for thioctacide - it should be applied at the dosage of 600-900 mg and 900-1200 mg, correspondingly. The method enables to selectively affect the immune system efficiently due to combined prescription of an immunimodulator and a preparation that accelerates its introduction at suppressing the activity of proinflammatory cytokines that prolongs disease remission due to preventing the development of immunological disorders.

EFFECT: higher efficiency of therapy.

3 ex

FIELD: medicine, narcology.

SUBSTANCE: method involves alternating comatose therapy and electroshock therapy every other day. In day carrying out the comatose therapy eserine ointment is placed in conjunctival sacs to patient and in 30 min 2-2.5 mg scopolamine hydrobromide solution is administrated as its 0.5% solution. Then in 3-5 h of comatose state patient is recovered from coma and 15-30 mg of physostigmine, 6 g of pyracetam, 7.5 g of magnesium sulfate and 400 ml of sodium hypochlorite are administrated by intravenous drops. In each next séance of comatose therapy dose of scopolamine hydrobromide is increased by 0.5 mg and brought about to 5-6 mg. In day carrying out electroshock therapy 1 ml of 0.1% solution of atropine sulfate and 2 ml of cordiamine are administrated and preliminary narcosis is carried out by intravenous administration of 200-300 mg of sodium thiopental or 100 mg of ketamine with simultaneous administration of 3-4 ml 2% ditiline solution and electroshock therapy is carried out followed by artificial lungs ventilation. Method provides enhancing effectiveness of treatment and to prolong the remission period.

EFFECT: enhanced effectiveness of treatment.

3 ex

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