Derivatives of sulfonamides, the method of production thereof and pharmaceutical composition

 

(57) Abstract:

The present invention relates to the derivatives of sulfonamides of General formula I, where-A=b-C=D - represents-CH=CH-CH=CH-group in which one CH can be replaced by N, AG denotes phenyl or naphthyl, unsubstituted or one-, two - or three-fold substituted with H, Hal, Q, Ph or NR4R5, R1, R2, R3each independently from each other, is absent or denotes H, Hal, a or Q, R4, R5each independently of one another denotes H or Q, Q denotes alkyl with 1-6 C-atoms, Ph represents phenyl, X denotes O or S, Hal denotes F, Cl, Br or I, n denotes 1, 2 or 3, as well as their salts. The compounds possess antagonistic towards the receptor endothelina properties, which allows them to apply for the treatment of diseases such as hypertension, heart failure, stroke. There is also described a method of production thereof and pharmaceutical composition based on derivatives of sulfonamides. 3 S. and 2 C.p. f-crystals, 1 table.

The invention relates to compounds of formula (I):

< / BR>
where

-A= B-C= D - represents-CH=CH-CH=CH-group, in which 1 or 2 CH may be replaced by nitrogen;

Ar denotes phenyl or naphthyl, unsubstituted or one-, two -, and the R5, NHCOR4, CF3, OCF3CN, OR4, COOR4, (CH2)nCOOR4, (CH2)nNR4R5, -N=C=O or NHCONR4R5phenyl or naphthyl;

R1, R2, R3each independently from each other, are absent or represent H, Gal, Q, CF3, NO2, NR4R5, CN, COOR4or CHCOR4;

R4, R5each independently of one another denote H or Q, or together also denote-CH2-(CH2)N-CH2-;

Q denotes alkyl with 1-6 C-atoms;

Ph denotes phenyl;

X denotes O or S;

Gal denotes F, Cl, Br or I;

"n" represents 1, 2 or 3;

and their salts, except 4-methyl-N-(2,1,3-benzothiadiazole - 5-yl)benzosulfimide, 4-nitro-N-(2,1,3-benzothiadiazole-5-yl)- benzosulfimide and 4-amino-N-(2,1,3-benzothiadiazole-5-yl)- benzosulfimide.

Similar compounds are known from European patent N 0558258 A1 and N 0569193 A1 and WIPO 94/27979.

4-methyl-N-(2,1,3-benzothiadiazole-5-yl)-benzosulfimide described in "Chemistry of heterocyclic compounds" (1968), 5, 812-814; 4-nitro-N-(2,1,3-benzothiadiazole-5-yl)benzosulfimide and 4-amino-N-(2,1,3-benzothiadiazole-5-yl)benzosulfimide described in GOH (1954), 24, 133-136.

For this connection is the task of obtaining new compounds with valuable properties, especially those that can be used for the preparation of drugs.

It was found that the compounds of formula (I) and their salts with good compatibility possess very valuable pharmacological properties. In particular, they are antagonistic against the endothelin receptor properties and therefore can be used to treat diseases such as hypertension, heart failure, coronary heart disease, renal, cerebral and myocardial ischemia, renal failure, stroke, subarachnoid haemorrhage, arteriosclerosis, pulmonary high blood pressure, inflammation, asthma, prostatic hyperplasia, endotoxic shock, and complications after the introduction of substances, as, for example, cyclosporine, and other associated activities of endothelin diseases.

Connection, incidentally, have a high affinity to subreceptors EMANDand ETB. These actions, you can define a regular in vitro and in vivo methods, such as described by P. D. Stein and others J. Med. Chem. 37 (1994), 329-331; and Ohlstein, E., and others, Proc. Natl. Acad. Sci. USA, 91 (1994), 8052-8056.

Blood pressure-lowering effect described by M. K. Bazil and others, J. Cardiovasc. Pharmacol. , 22 (1993), 897-905; and J. Lange and others, Lab. Animal. 20, (1991 the drugs in medicine and veterinary medicine, in particular for the prophylaxis and/or therapy of diseases of the heart, circulation and blood vessels, primarily hypertension and congestive heart failure.

The subject invention are the compounds of formula (I) and their salts, as well as the method of obtaining these compounds, as well as their salts, characterized in that

(a) compound of formula (II):

< / BR>
where

-A= B-C= D-; R1, R2, R3and X are specified in paragraph 1 of the claims value;

enter into interaction with the compound of the formula (III):

Ar-SO2-E (III), where

E denotes Cl, Br, I or a free or reactive functionally modified OH-group; and

Ar has specified in paragraph 1 of the claims value;

or,

(b) to obtain the compounds of formula (I), where X denotes sulfur, to obtain 4-methyl-N-(2,1,3-benzothiadiazole-5-yl)benzene - sulfonamida, 4-nitro-N-(2,1,3-benzothiadiazole-5-yl) benzosulfimide and 4-amino-N-(2,1,3-benzothiadiazole-5-yl) benzosulfimide.

The compound of formula (IV):

< / BR>
where-A=B-C=D-a, Ar, R1, R2and R3are specified in paragraph 1 of the claims values,

enter into interaction with thionyl chloride or a reactive derivative of this compound;

or
< / BR>
where-A=B-C=D-a, Ar, R1, R2and R3are specified in paragraph 1 of the claims values, restore;

and/or the compound of formula (I) one or more residues1, R2and/or R3turn in one or more residues R1, R2and/or R3that:

I) the nitro group is reduced to amino group;

II) bromo-Deputy substituted with cyano group;

III) cyano group, hydrolyzing to the carboxyl group;

IV) a carboxyl group atrificial to ester groups;

V) amino group by reductive amination in turn alkilirovanny amine; or

VI) acelerou amino group;

and/or a base or acid of the formula (I) turn in one of their salts.

Above - and below residues, respectively parameters A=B-C=D-a, Ar, R1-R5, Q, Ph, X-Gal and n have the above in the case of formula (I): (V) values, unless nothing else.

In the above formulas, Q contains 1-6, preferably 1,2,3 or 4 C-atoms. Q preferably denotes methyl; further, ethyl, propyl, isopropyl, butyl, isobutyl, sec.-butyl or tert.- butyl; hereinafter, also pencil; 1-, 2 - or 3-methylbutyl; 1,1-, 1,2 - or 2,2-dimethylpropyl; 1-Etiler is 1-ethyl-2-methyl-propyl; 1, 1,2 - or 1,2,2-trimethylpropyl.

Alkenyl preferably denotes vinyl; 1 - or 2-propenyl; 1-butenyl; further, 1-pentanol or 1-hexenyl.

Gal preferably denotes F, Cl or Br, but also I.

Ar denotes unsubstituted, preferably as indicated - monosubstituted phenyl or naphthyl, particularly preferably phenyl; o - or m-tolyl; o-, m - or p-ethylphenyl; o-, m - or p-propylphenyl; o-, m - or p-isopropylphenyl; o-, m - or p - tert.-butyl-phenyl; o-, m - or p-triptoreline; o-, m - or p - phenylphenol; o-, m - or p-hydroxyphenyl; o - or m-nitrophenyl; o - or m-AMINOPHENYL; o-, m - or p-methylaminophenol; o-, m - or p - dimethylaminophenyl; o-, m - or p-acetamidophenyl; o-, m - or p- (triptoreline) phenyl; o-, m - or p-tianfeng; o-, m - or p- (N-pyrrolidino) phenyl; o-, m - or p-(N-piperidino) phenyl; o-, m - or p-methoxyphenyl; o-, m - or p-ethoxyphenyl; o-, m - or p - phenoxyphenyl; o-, m - or p-carboxyphenyl; o-, m - or p - ethoxycarbonylphenyl; o-, m - or p-ethoxycarbonylphenyl; o-, m - or p-(carboxymethyl) phenyl; o-, m - or p-(methoxycarbonylmethyl) phenyl; o-, m - or p-(methoxycarbonylethyl) phenyl; o-, m - or p- (aminomethyl) phenyl; o-, m - or p-(N-methylaminomethyl)phenyl; o-, m - or p-(N,N-dimethyl-amino) phenyl; o-, m - or p" (N-ethylamino) phenyl; o-, m - is, or p-(N-piperidinomethyl) -phenyl; o-, m - or p-isocyanatophenyl; o-, m - or p-carbimidoyl; o-, m - or p-(N-methylcarbamoyl) phenyl; o-, m - or p-(N, N - dimethylcarbamoyl) phenyl; o-, m - or p-forfinal; o-, m - or p - bromophenyl; o-, m - or p-chlorophenyl; further, preferably naphthyl; 5-methyl-naphthyl; 5-ethyl - naphthyl; 5-propylheptyl; 5-isopropylate; 5-tert.-butyl - naphthyl; 5 - triptoreline; 5-venilated; 5-hydroxynaphthyl; 5 - nitronate; 5-aminonaphthol; 5-N-methylamino-naphthyl; 5-N,N - dimethylaminomethyl; 5-acetamidomethyl; 5-(triptoreline) naphthyl; 5-cyan-naphthyl; 5-(N-pyrrolidino) naphthyl; 5-(N-piperidino) naphthyl; 5 - methoxy-naphthyl; 5-ethoxy-naphthyl; 5-carboxy-naphthyl; 5-methoxycarbonyl-naphthyl; 5-etoxycarbonyl-naphthyl; 5-(carboxymethyl) naphthyl; 5- (methoxycarbonylmethyl) naphthyl; 5-(ethoxycarbonylmethyl) naphthyl; 5-(aminomethyl) naphthyl; 5-(N-methylaminomethyl) naphthyl; 5-(N, N-dimethylaminomethyl) naphthyl; 5-(N-ethylamino) naphthyl; 5-(N,N - diethylamino) naphthyl; 5-(N-pyrrolidinyl) naphthyl; 5-(N - piperidinomethyl) naphthyl; 5-isocyanatomethyl; 5-carbimidoyl; 5- (N-methylcarbamoyl) naphthyl; 5-(N, N-dimethylcarbamoyl) naphthyl; 5 - N-isopropylamino-naphthyl; 5-N-isopropyl-N-methyl-amino - naphthyl; 5-fluoro-naphthyl; 5-chloro-naphthyl; 5-bromo-naphthyl; further, preferably 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-differenl; 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-dichlor the-, 2-methyl-4 - chloro-, 2-methyl-5-chloro-, 2-methyl-6-chloro-, 3-chloro-4-methyl-, 3-chloro - 5-methyl - or 3-methyl-4-chloro-phenyl; 2-bromo-3-methyl-, 2-bromo-4 - methyl-, 2-bromo-5-methyl-, 2-bromo-6-methyl-, 2-methyl-3-bromo-, 2 - methyl-4-bromo-, 2-methyl-5-bromo-, 2-methyl-6-bromo-, 3-bromo-4-methyl-, 3-bromo-5-methyl - or 3-methyl-4-bromo-phenyl; 2,4 - or 2,5-dinitro-phenyl; 2,5 - or 3,4-dimethoxy-phenyl; 3-nitro-4-chloro-phenyl; 2 - amino-3-chloro-, 2-amino-4-chloro-, 2-amino-5-chloro - or 2-amino-6 - chloro-phenyl; 2-nitro-4-N,N-dimethylamino - 3-nitro-4-N,N - dimethylamino - phenyl; 3-carboxy-2-methoxy-, 3-carboxy-4-methoxy - or 3-carboxy-5-methoxy-phenyl; 2,3,4-, 2,3,5-, 2,3,6-, 2,4,6- or 3,4,5-trichloro-phenyl; 2, 4, 6-tri-tert.-butyl-phenyl; further, preferably 2-nitro-4-(trifluoromethyl) -phenyl; 3, 5-di- (trifluoromethyl) -phenyl; 2,5-dimethyl-phenyl; 2-hydroxy-3,5-dichloro - phenyl; 2-fluoro-5 - or 4-fluoro-3-(trifluoromethyl) phenyl; 4-chloro-2 - or 4-chloro-3-(trifluoromethyl)-, 2-chloro-4 - or 2-chloro-5-(trifluoromethyl)- phenyl; 4-bromo-2-or 4-bromo-3-(trifluoromethyl)-phenyl; p-iodine-phenyl, p - vinyl-phenyl; 5-(N,N-dibutylamino) naphthyl; 2-nitro-4-methoxy - phenyl; 2, 5-dimethoxy-4-nitrophenyl; 3, 5-dicarboxy-phenyl; 2 - chloro-3-nitro-5-carboxy-phenyl; 4-chloro-3-carboxy-phenyl; 2-methyl-5 - nitro-phenyl; 2,4-dimethyl-3-nitro-phenyl; 3, 6-dichloro-4-amino - phenyl; 4-fluoro-3-chlorophenyl; 4-fluoro-3, 5-dimethyl-phenyl; 2-fluoro-4 - bromo-phenyl; 2, 5-debtor-4-bromo-phenyl; 2 and-phenyl; 2-methoxy-5-methyl-phenyl or 2,4,6-triisopropyl-phenyl.

The rest-A= B-C=D preferably represents-CH=CH-CH=N-; next, -CH= N-CH=CH - or-CH=N-CH=N-, however, particularly preferably-CH=CH-CH=CH-.

The remains of R1, R2and R3each, independently of one another, preferably denote H, Q (in particular CH3), Gal, in particular chlorine or bromine, further, however, also preferably NO2or CF3.

The parameter "n" preferably denotes 0 or 1, and further preferably 2.

The compounds of formula (I) can have one or more chiral centers and therefore may exist in different stereoisomeric forms. Formula (I) includes all these forms.

Accordingly, the subject invention are in particular those compounds of formula (I) in which at least one of these residues has one of the abovementioned preferred meanings. Some preferred groups of compounds can be expressed by the following partial formulas (1A): (1G), which correspond to the formula (I) and where more not mentioned residues are specified in the case of the formula (I) value, where, however:

1A: X denotes sulfur,

in 1B: X denotes oxygen;

in 1B: X oboznachaet oxygen and-A=B-C=D - represents-CH=CH-CH=N-;

in 1E: X is sulfur; -A=B-C=D - represents-CH=CH-CH=CH-;

R1denotes hydrogen; R2indicates Gal and R3denotes methyl;

in 1G: Ar represents 5-(N,N-dimethylamino)naphthyl.

The compounds of formula (I) and also the source materials for their production, however, get itself known methods, which are described in the literature (for example in standard works, as Houben-Weil, methods of organic chemistry, ed. Georg-Thieme, Stuttgart, in particular, however, in the European patent 0569193 A1 and WIPO-94/27979), namely under reaction conditions which are known and suitable for the specified transformations. You can also use itself known here more not mentioned options.

The source of the substance, if desired, can also be obtained in situ, so they are not isolated from the reaction mixture, and immediately injected into the interaction further, to obtain the compounds of formula (I).

The compounds of formula (I) can preferably be obtained by the fact that the compounds of formula (II) enter into an interaction with compounds of the formula (III).

In the compounds of the formula (III) E preferably denotes Cl, Br, I or a reactive modified OH - group as alkyl-sulfonyloxy group with 1-6 C-ateno phenyl - or p-tolilsulfonil-group).

The interaction is typically carried out in an inert solvent in the presence of one or more bases, preferably in the presence of a tertiary amine, e.g. triethylamine, pyridine, 4-dimethylaminopyridine, expediently at temperatures 0-150oC, preferably at 40-90oC. the Excess amine may also serve as solvent.

As inert solvents are suitable, for example, hydrocarbons as hexane, petroleum ether, benzene, toluene or xylene; chlorinated hydrocarbons, such as trichloroethylene, 1,2-dichloroethane, carbon tetrachloride, chloroform or dichloromethane; alcohols, like methanol, ethanol, isopropanol, n-propanol, n-butanol, or tert. -butanol; ethers like diethyl ether, diisopropyl ether, tetrahydrofuran (THF) or dioxane; a simple glycol ethers as simple etilenglikolevye or monotropy ether (methylglycol or ethylglycol), etilenglikolevye simple ether (diglyme); ketones, such as acetone or butanone; amides, as ndimethylacetamide, dimethylacetamide or dimethylformamide (DMF); NITRILES like acetonitrile; sulfoxidov as dimethyl sulfoxide (DMSO); carbon disulfide; carboxylic acids, as formic acid or acetic acid; neither the lei.

The initial compounds of the formula (II), as a rule, are new. However, you can get them in itself known methods. So, for example, 5-amino-6-methyl-2,1,3-benzothiadiazole can be obtained by hydrogenation in the presence of Raney Nickel in an inert solvent like methanol, 5-nitro-6-methyl-2,1,3-benzothiadiazole. This reaction is expediently carried out at temperatures of 0 to approximately 200oC, preferably operate at 30-80oC.

The compounds of formula (I), where X denotes S, next, you can get the fact that the compounds of formula (IV), which, as a rule, are new, enter into interaction with thionyl chloride or a reactive derivative of this compound, as, for example, timileyin, similar to the known methods described in the literature (for example, J. Heterocycl. Chem. 7, 629 (1970)), in an inert solvent, in the presence of one or more bases, preferably tertiary amines, such as triethylamine, pyridine, 4-dimethylaminopyridine, expediently at temperatures 0-150oC, preferably at 40-90oC. the Excess amine may also serve as solvent.

The compounds of formula (I), where X denotes Oh, then, you can get the fact that the compounds of formula (V)/SUB>, PCl3, Na2S2O4Ph3P or P(OC2H5)3similar well-known methods, which are described in the literature (for example, Tetrahedron 44, 5209 (1988); Tetrahedron, 48, 8199 (1922); Z. Chem. 20, 257 (1980); J. Org. Chem. 47, 1774 (1982); J. Org. Chem. 28, 1656 (1963) or J. Med. Chem. 11, 305 (1968)).

The initial compounds of the formula (V) can be obtained in itself known methods. So, for example, 4-tert. -butyl - N-(2,1,3-benzoxadiazole-1-N-oxide-5-yl)benzosulfimide can be obtained by reacting with sodium azide in the catalysis of the transfer phases of 4-tert.-butyl-N-(4-chloro-3-nitro) - benzosulfimide through 4-tert.-butyl-N-(4-azido-3 - nitro)benzosulfimide and subsequent cyclization in glacial acetic acid.

Further, the compound of formula (I) can be converted into another compound of formula (I) having one or more residues1, R2and/or R3turn in one or more residues R1, R2and/or R3the fact that the nitro-group, e.g. by hydrogenation in the presence of Raney Nickel or palladium-on-coal in an inert solvent like methanol or ethanol, reduced to amino groups; and/or bromo-substituents by introducing into the interaction, for example, with copper cyanide(I), in turn cyano group; and/or the interaction with alcohols; and/or nitro groups alkylate when gidroenergetichesky conditions, and get alkylated amines.

Furthermore, free amino groups in the usual way, you can allievate using the acid chloride or acid anhydride or alkilirovanii with unsubstituted or substituted alkylhalogenide, expediently in an inert solvent like dichloromethane or THF, and/or in the presence of a base like triethylamine or pyridine, at temperatures from -60oC to +30oC.

In the desirable case, the compound of formula (I) can reclaim the functionally modified amino and/or hydroxyl group by solvolysis or hydrogenolysis using conventional methods. For example, the compound of formula (I), which contains NHCOR4or COOR4group, can be converted into the corresponding compound of formula (I), which instead of the specified group contains NH2- or COOH-group. COOR4groups can omelet, for example, using NaOH or KOH in water, mixtures of water with THF or water with dioxane at temperatures of 0-100oC.

The basis of the formula (I) with acids can be converted to the corresponding salt accession acid, for example, by introducing into the interaction is equivalent to the treatment used, in particular, the acid, which give physiologically acceptable salts. Thus, it is possible to use inorganic acids, for example sulfuric acid, nitric acid, halogen acids as hydrochloric acid or Hydrobromic acid, phosphoric acid, like phosphoric acid, sulfamic acid; further, organic acids, in particular aliphatic, alicyclic, analiticheskie, aromatic or heterocyclic one - or polybasic carboxylic, sulfonic or sulfuric acids, such as formic acid, acetic acid, propionic acid, pavlikova acid, diethyloxalate acid, malonic acid, succinic acid, Emelyanova acid, fumaric acid, maleic acid, lactic acid, tartaric acid, malic acid, citric acid, gluconic acid, ascorbic acid, nicotinic acid, isonicotinamide acid, methane - or econsultation, ethicalfashion, 2-hydroxy - econsultation, benzosulfimide, p-toluensulfonate, naphthalene mono - and di-sulfonic acids, louisanna acid. Salts with physiologically unacceptable acids, for example, picrate, can be used for identifying and/or purifying compounds of formula (I).

The subject of the invention, then, is the use of compounds of formula (I) and/or 4-methyl-N-(2,1,3-benzothiadiazole-5 - yl)benzosulfimide and/or 4-nitro-N-(2,1,3-benzothiadiazole - 5-yl)benzosulfimide and/or 4-amino-N-(2,1,3 - benzothiadiazole-5-yl) benzosulfimide and/or their physiologically acceptable salts for the preparation of pharmaceutical compositions, in particular by non-chemical. While their together with at least one solid, liquid and/or semi-liquid carrier or auxiliary substance and, if necessary, in combination with one or more other biologically active substances brought to a suitable dosage forms.

The subject of the invention, further, are pharmaceutical compositions containing at least one compound of formula (I) and/or 4-methyl-N-(2,1,3-benzothiadiazole-5-yl)-benzosulfimide and/or 4-nitro-N-(2,1,3-benzothiadiazole-5-yl)benzosulfimide and/or 4-amino-N-(2,1,3-benzothiadiazole-5-yl)benzosulfimide and/or one of their physiologically acceptable salts.

These compositions can be used as drugs in medicine or veterinarinary, oral), parenteral or topical administration and do not react with the new compounds, for example water, vegetable oils, benzyl alcohols, alkalophile, polyethylene glycols, glycerol triacetate, gelatin, carbohydrates as lactose or starch, magnesium stearate, talc, vaseline. For oral administration are, in particular, tablets, pills, coated tablets, capsules with the medicine, powders, granules, syrups, juices or drops; for rectal use candles; for parenteral administration are solutions, preferably oily or aqueous solutions, furthermore, suspensions, emulsions or implants; for topical application are ointments, creams or powders. The new compounds can also be liofilizirovanny and received lyophilizate to apply, for example, for the preparation of drugs for injection. These compositions can be sterilized and/or may contain auxiliary substances, as imparting lubricity agents, preservatives, stabilizers and/or wetting, emulsifying agents, salts for influencing the osmotic pressure, buffer substances, colorants, flavouring substances, flavouring substances and/or some other biologically active substances, for example one or more vitamins.

This proposed according to the invention the substance is usually administered preferably in dosages of about 1-500 mg, in particular between 5 and 100 mg per dosage unit. The daily dose is preferably about 0.02 to 10 mg/kg of body weight. Special dose for each patient depends, however, on various factors, for example, the effectiveness of used special compound, the age, body weight, General health, sex, on cost, time and route of administration, rate of excretion, combination of drugs and the severity of the respective disease, which has implications for therapy. Preferably oral administration.

Above and below, all temperatures are given inoC. In the following examples, the expression "conventional treatment" means add, if necessary, water; establish, if required, depending on the structure of the target product, the pH value in the range 2-10; extracted with ethyl acetate or dichloromethane; the phases are separated; the organic phase is dried over sodium sulfate, evaporated and the residue purified by chromatography on silica gel and/or by crystallization. RfBR> To a solution of 1.53 g of 5-amino-2,1,3-benzothiadiazole obtained by hydrogenation of 5-nitro-2,1-3-benzothiadiazole on Raney Nickel in methanol in 15 ml of pyridine, add a solution of 3 g of 5 - dimethylamino-naphthalene-sulfochloride ("And") in 10 ml of pyridine, the mixture is stirred for 24 hours at 60oC, then added to 75 ml of 2 n hydrochloric acid and processed as usual. Get a 5-dimethylamino-N- (2,1,3-benzothiadiazole-5-yl)-1-naphthalenesulfonate in a solid yellow color. So pl. =73oC; potassium salt, so pl. >300oC.

Similarly, of the following mZ-5-amino-2,1,3 - benzothiadiazole, where mZ denotes:

4-methyl; 6-methyl; 7-methyl; 4,6-dimethyl; 4,7-dimethyl; 6,7-dimethyl; 4-trifluoromethyl; 6-trifluoromethyl; 7-trifluoromethyl, 4-bromo, 6-bromo; 7-bromo; 4,6-dibromo; 4,7-dibromo; 6,7-dibromo; 4-bromo-6-methyl; 4-bromo-7-methyl; 6-bromo-7-methyl; 4-methyl-6-bromo, and 4-methyl-7 - bromo; 6-methyl-7-bromo, 4-bromo-6-ethyl; 4-bromo-7-ethyl; 6-bromo-7-ethyl; 4-ethyl-6-bromo, 4-ethyl-7-bromo; 6-ethyl-7-bromo, 4-bromo-6 - trifluoromethyl; 4-bromo-7-trifluoromethyl; 6-bromo-7-trifluoromethyl, 4 - trifluoromethyl-6-bromo, 4-trifluoromethyl-7-bromo; 6-trifluoromethyl-7 - bromo; 4-chloro; 6-chloro; 7-chloro; 4-nitro; 6-nitro; 7-nitro; 4-bromo-6 - tert.-butyl; 4-bromo-7-tert. -butyl; 6-bromo-7-tert.-butyl; 4-tert.- butyl 6-bromo; 4-tert.-butyl-7-bromo; 6-tert. -butyl-7-bromo; 4 halamine group; 7-dimethylamino-group; 4-cyan; 6-cyan; 7 - cyan; 4-methoxycarbonyl; 6-methoxycarbonyl; 7-methoxycarbonyl; 4-etoxycarbonyl; 6-etoxycarbonyl; 7-etoxycarbonyl; 4-acetamido; 6-acetamido; 7-acetamido group; by entering into interaction with "A" will receive the following 5-dimethylamino-mZ-1 - naphthalenesulfonate, where mZ denotes:

N-(4-methyl-2,1,3-benzothiadiazole-5-yl), so pl. 159oC;

N-(6-methyl-2,1,3-benzothiadiazole-5-yl);

N-(7-methyl-2,1,3-benzothiadiazole-5-yl);

N-(4,6-dimethyl-2,1,3-benzothiadiazole-5-yl);

N-(4,7-dimethyl-2,1,3-benzothiadiazole-5-yl);

N-(6,7-dimethyl-2,1,3-benzothiadiazole-5-yl);

N-(4-trifluoromethyl-2,1,3-benzothiadiazole-5-yl);

N-(6-trifluoromethyl-2,1,3-benzothiadiazole-5-yl);

N-(7-trifluoromethyl-2,1,3-benzothiadiazole-5-yl);

N-(4-bromo-2,1,3-benzothiadiazole-5-yl), so pl. 151oC;

N-(6-bromo-2,1,3-benzothiadiazole-5-yl);

N-(7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4,6-dibromo-2,1,3-benzothiadiazole-5-yl);

N-(4,7-dibromo-2,1,3-benzothiadiazole-5-yl);

N-(6,7-dibromo-2,1,3-benzothiadiazole-5-yl);

N-(4-bromo-6-methyl-2,1,3-benzothiadiazole-5-yl);

N-(4-bromo-7-methyl-2,1,3-benzothiadiazole-5-yl);

N-(6-bromo-7-methyl-2,1,3-benzothiadiazole-5-yl);

N-(4-methyl-6-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-methyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(6-metasol-5-yl);

N-(6-bromo-7-ethyl-2,1,3-benzothiadiazole-5-yl);

N-(4-ethyl-6-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-ethyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(6-ethyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-bromo-6-trifluoromethyl-2,1,3-benzothiadiazole-5-yl);

N-(4-bromo-7-trifluoromethyl-2,1,3-benzothiadiazole-5-yl);

N-(6-bromo-7-trifluoromethyl-2,1,3-benzothiadiazole-5-yl);

N-(4-trifluoromethyl-6-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-trifluoromethyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(6-trifluoromethyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-chloro-2,1,3-benzothiadiazole-5-yl), so pl. 168oC;

N-(6-chloro-2,1,3-benzothiadiazole-5-yl);

N-(7-chloro-2,1,3-benzothiadiazole-5-yl);

N-(4-nitro-2,1,3-benzothiadiazole-5-yl);

N-(6-nitro-2,1,3-benzothiadiazole-5-yl);

N-(7-nitro-2,1,3-benzothiadiazole-5-yl);

N-(4-bromo-6-tert.-butyl-2,1,3-benzothiadiazole-5-yl);

N-(4-bromo-7-tert.-butyl-2,1,3-benzothiadiazole-5-yl);

N-(6-bromo-7-tert.-butyl-2,1,3-benzothiadiazole-5-yl);

N-(4-tert.-butyl 6-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-tert.-butyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(6-tert.-butyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-chloro-6-methyl-2,1,3-benzothiadiazole-5-yl);

N-(4-chloro-7-methyl-2,1,3-benzothiadiazole-5-yl);

N-(6-chloro-7-methyl-2,1,3-benzothiadiazole-5-yl);

N-(4-methyl-6-chloro-2,1,3-benzothia the-dimethylamino-2,1,3-benzothiadiazole-5-yl);

N-(6-dimethylamino-2,1,3-benzothiadiazole-5-yl);

N-(7-dimethylamino-2,1,3-benzothiadiazole-5-yl);

N-(4-cyan-2,1,3-benzothiadiazole-5-yl);

N-(6-cyan-2,1,3-benzothiadiazole-5-yl);

N-(7-cyan-2, 1,3-benzothiadiazole-5-yl);

N-(4-methoxycarbonyl-2,1,3-benzothiadiazole-5-yl);

N-(6-methoxycarbonyl-2,1,3-benzothiadiazole-5-yl);

N-(7-methoxycarbonyl-2,1,3-benzothiadiazole-5-yl);

N-(4-etoxycarbonyl-2,1,3-benzothiadiazole-5-yl);

N-(6-etoxycarbonyl-2,1,3-benzothiadiazole-5-yl);

N-(7-etoxycarbonyl-2,1,3-benzothiadiazole-5-yl);

N-(4-acetamido-2,1,3-benzothiadiazole-5-yl);

N-(6-acetamido-2,1,3-benzothiadiazole-5-yl);

N-(7-acetamido-2,1,3-benzothiadiazole-5-yl).

Similarly, by introducing into the interaction of 4-amino - 2,1,3-benzothiadiazole with "And" receive 5-dimethylamino-N-(2,1,3 - benzothiadiazole-4-yl)-1-naphthalene-sulfonamide, so pl. 81oC; and of the following 4-amino-mZ-2,1,3-benzothiadiazole, where mZ denotes: 5-methyl; 6-methyl; 7-methyl; 5,6-dimethyl; 5,7-dimethyl; 6,7-dimethyl; 5-trifluoromethyl; 6-trifluoromethyl; 7-trifluoromethyl; 5 - bromo, 6-bromo; 7-bromo; 5,6-bromo; 5,7-bromo; 6,7-dibromo; 5-bromo-6 - methyl; 5-bromo - 7-methyl; 6-bromo-7-methyl; 5-methyl-6-bromo; 5-methyl-7 - bromo; 6-methyl - 7-bromo, 5-bromo-6-ethyl; 5-bromo-7-ethyl; 6-bromo-7 - ethyl; 5-ethyl-6-bromo; 5-ethyl-7-bromo; 6-ethyl-7-bromo, 5-bromo-6 - crypto is bromine; 5-chloro; 6-chloro; 7-chloro, 5-nitro-group; 6-nitro-group; 7 - nitro -; 5-bromo-6-tert. -butyl; 5-bromo-7-tert. -butyl; 6 - bromo-7-tert.-butyl; 5-tert.- butyl 6-bromo; 5-tert.-butyl-7-bromo; 6-tert.-butyl-7-bromo; 5-chloro-6-methyl; 5-chloro-7-methyl; 6-chloro-7 - methyl; 5-methyl-6-chloro; 5-methyl-7-chloro; 6-methyl-7-chloro; 5 - dimethylamino group; 6-dimethylamino group; 7-dimethyl-amino group; 5-cyan 6-cyan; 7-cyan; 5-methoxycarbonyl; 6 - methoxycarbonyl; 7-methoxycarbonyl; 5-etoxycarbonyl; 6 - etoxycarbonyl; 7-etoxycarbonyl; 5-atsetamino group; 6-acetamido group; 7-acetamido group; by entering into interaction with "A" will receive the following 5-dimethylamino-mZ-1-naphthalenesulfonate, where mZ denotes:

N-(5-methyl-2,1,3-benzothiadiazole-4-yl), so pl. 154oC;

N-(6-methyl-2,1,3-benzothiadiazole-4-yl);

N-(7-methyl-2,1,3-benzothiadiazole-4-yl), so pl. 170oC;

N-(5,6-dimethyl-2,1,3-benzothiadiazole-4-yl);

N-(5,7-dimethyl-2,1,3-benzothiadiazole-4-yl);

N-(6,7-dimethyl-2,1,3-benzothiadiazole-4-yl);

N-(5-trifluoromethyl-2,1,3-benzothiadiazole-4-yl), so pl. 182oC;

N-(6-trifluoromethyl-2,1,3-benzothiadiazole-4-yl);

N-(7-trifluoromethyl-2,1,3-benzothiadiazole-4-yl);

N-(5-bromo-2,1,3-benzothiadiazole-4-yl);

N-(6-bromo-2,1,3-benzothiadiazole-4-yl);

N-(7-bromo-2,1,3-benzothiadiazole-4-yl);

N-(5,6-dibromo-2,1,3 N-(5-bromo-6-methyl-2,1,3-benzothiadiazole-4-yl);

N-(5-bromo-7-methyl-2,1, 3-benzothiadiazole-4-yl);

N-(6-bromo-7-methyl-2,1,3-benzothiadiazole-4-yl);

N-(5-methyl-6-bromo-2,1,3-benzothiadiazole-4-yl);

N-(5-methyl-7-bromo-2,1,3-benzothiadiazole-4-yl);

N-(6-methyl-7-bromo-2,1,3-benzothiadiazole-4-yl);

N-(5-bromo-6-ethyl-2,1, 3-benzothiadiazole-4-yl);

N-(5-bromo-7-ethyl-2,1,3-benzothiadiazole-4-yl);

N-(6-bromo-7-ethyl-2,1,3-benzothiadiazole-4-yl);

N-(5-ethyl-6-bromo-2,1,3-benzothiadiazole-4-yl);

N-(5-ethyl-7-bromo-2,1,3-benzothiadiazole-4-yl);

N-(6-ethyl-7-bromo-2,1, 3-benzothiadiazole-4-yl);

N-(5-bromo-6-trifluoromethyl-2,1,3-benzothiadiazole-4-yl);

N-(5-bromo-7-trifluoromethyl-2,1,3-benzothiadiazole-4-yl);

N-(6-bromo-7-trifluoromethyl-2,1,3-benzothiadiazole-4-yl);

N-(5-trifluoromethyl-6-bromo-2,1,3-benzothiadiazole-4-yl);

N-(5-trifluoromethyl-7-bromo-2,1,3-benzothiadiazole-4-yl);

N-(6-trifluoromethyl-7-bromo-2,1,3-benzothiadiazole-4-yl);

N-(5-chloro-2,1,3-benzothiadiazole-4-yl);

N-(6-chloro-2,1,3-benzothiadiazole-4-yl);

N-(7-chloro-2,1,3-benzothiadiazole-4-yl);

N-(5-nitro-2,1,3-benzothiadiazole-4-yl);

N-(6-nitro-2,1,3-benzothiadiazole-4-yl);

N-(7-nitro-2,1,3-benzothiadiazole-4-yl);

N-(5-bromo-6-tert.-butyl-2,1,3-benzothiadiazole-4-yl);

N-(5-bromo-7-tert.-butyl-2,1,3-benzothiadiazole-4-yl);

N-(6-bromo-7-tert.-butyl-2,1,3-benzothiadiazole-4-yl);

N-(5-tert.-butyl-6-benzothiadiazole-4-yl);

N-(5-chloro-6-methyl-2,1,3-benzothiadiazole-4-yl);

N-(5-chloro-7-methyl-2,1,3-benzothiadiazole-4-yl);

N-(6-chloro-7-methyl-2,1,3-benzothiadiazole-4-yl), so pl. 170oC;

N-(5-methyl-6-chloro-2,1,3-benzothiadiazole-4-yl);

N-(5-methyl-7-chloro-2,1,3-benzothiadiazole-4-yl);

N-(6-methyl-7-chloro-2,1, 3-benzothiadiazole-4-yl);

N-(5-dimethylamino-2,1,3-benzothiadiazole-4-yl);

N-(6-dimethylamino-2,1,3-benzothiadiazole-4-yl);

N-(7-dimethylamino-2,1,3-benzothiadiazole-4-yl);

N-(5-cyan-2,1,3-benzothiadiazole-4-yl);

N-(6-cyan-2,1,3-benzothiadiazole-4-yl);

N-(7-cyan-2,1,3-benzothiadiazole-4-yl);

N-(5-methoxycarbonyl-2,1,3-benzothiadiazole-4-yl);

N-(6-methoxycarbonyl-2,1,3-benzothiadiazole-4-yl);

N-(7-methoxycarbonyl-2,1,3-benzothiadiazole-4-yl);

N-(5-etoxycarbonyl-2,1,3-benzothiadiazole-4-yl);

N-(6-etoxycarbonyl-2,1,3-benzothiadiazole-4-yl);

N-(7-etoxycarbonyl-2,1,3-benzothiadiazole-4-yl);

N-(5-acetamido-2,1,3-benzothiadiazole-4-yl);

N-(6-acetamido-2,1,3-benzothiadiazole-4-yl);

N-(7-acetamido-2,1,3-benzothiadiazole-4-yl);

Example 2

To a solution of a 3.01 g of 4-tert.-butyl-N-(1,2-diamino-4-phenyl)- 1-benzosulfimide and 4.1 g of triethylamine in 100 ml of toluene added a solution of 3 g of thionyl chloride in 15 ml of toluene, the mixture is heated for 1 hour at 110oC, is treated as a normal way, by introducing into the interaction of N-(1,2 - diamino-4-phenyl)-1 - benzosulfimide with thionyl chloride receive N-(2,1,3 - benzothiadiazole-5-yl)-1-benzosulfimide; and by similar interactions the following N-(1,2-diamino-4-phenyl)-mZ-1 - benzosulfimide, where mZ denotes:

4-fluoro; 4-chloro; 4-bromo, 4-iodine; 4-ethyl; 4-propyl; 4-isopropyl; 3,4-dimethyl; 2,5-dimethyl; 2,5-diethyl -; 2,4-diethyl -; 2,5-dipropyl; 3-acetamido-group; 4-acetamido-group; 2-cyan; 3-carboxyl; 2 triptoreline group; 3-nitro group; a 4-nitro group; a 2-nitro - 5-methyl; 2-methyl-5-nitro -; 2-ethyl-5-nitro-group; 2,4,6-tri-methyl; 2,4-dichloro; 2,5-dichloro; 3,4-dichloro; 3,5-dichloro; 5-bromo-2-methoxy; 5-bromo-2-methyl; 5-bromo-2-ethyl; 5-bromo-2-propyl; 2,5-debtor; 3,6-debtor; 2,5-dimethoxy-group; 3,4-dimethoxy-group; 3-trifluoromethyl; 4-trifluoromethyl; 3,5-di-(trifluoromethyl); 2,4,5-tri-chloro; 2-chloro-4-fluoro; 3-chloro-5-fluoro; 2-chloro-5-methyl; 3-chloro-2-methyl -; 5-chloro-2-methoxy -; 2-butyl - 5-bromo; 2-bromo-5-butyl; 2-bromo-5-propyl; 5-fluoro-2-methyl; 2-phenyl; 4-tolyl; 2-bromo-5-ethyl; with thionyl chloride receive the following N-(2,1,3-benzothiadiazole - 5-yl)-mZ-1-benzosulfimide, where mZ denotes:

4-fluoro; 4-chloro; 4-bromo; so pl. 195oC; 4-iodine; 4-ethyl; 4-propyl; 4-isopropyl; 3,4-dimethyl; 2,5-dimethyl; 2,5-diethyl -; 2,4-diethyl -; 2,5-dipropyl; 3-acetamido-group; 4-acetamido-gr is the SCP; 2-ethyl-5-nitro - group; 2,4,6-trimethyl; 2,4-dichloro; 2,5-dichloro; 3,4-dichloro; 3,5 - di-chloro, 5-bromo-2-methoxy group; 5-bromo-2-methyl, T. pl. 185oC; 5 - bromo-2-ethyl; 5-bromo-2-propyl, so pl. 182oC; 2.5-debtor; 3,6-debtor; 2,5-dimethoxy-group; 3,4-dimethoxy-group; 3-trifluoromethyl, 4 - trifluoromethyl; 3,5-di(trifluoromethyl); 2,4,5-trichloro; 2-chloro-4-fluoro; 3-chloro-5-fluoro; 2-chloro-5-methyl; 3-chloro-2-methyl -; 5-chloro-2-methoxy -; 2-butyl-5-bromo; 2-bromo-5-butyl; 2-bromo-5-propyl, so pl. 299oC; 5-fluoro-2-methyl; 2-phenyl, so pl. 175oC; 4-tolyl, so pl. 220oC; 2 - bromo-5-ethyl, T. pl. 183oC.

Example 3

A solution of 1 g of 5-dimethylamino-N-(2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide)-1-naphthalenesulfonate (obtained by heating 5-dimethylamino-N-(1-azido-2-nitro-4-phenyl) -1 - naphthalenesulfonate in glacial acetic acid) and 5 ml of triethylphosphite in 50 ml of absolute ethanol is heated for 30 minutes at 75oC. After removal of the solvent and the normal processing gain 5-dimethylamino-N-(2,1,3-benzoxadiazole-5-yl)-1 - naphthalenesulfonate, so pl. 106oC.

Similarly, by reacting the following 5-di - methylamino-mZ-1-naphthalenesulfonate, where mZ denotes:

N-(4-methyl-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(6-methyl-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(4, 7-dimethyl-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(6,7-dimethyl-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(4-trifluoromethyl-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(6-trifluoromethyl-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(7-trifluoromethyl-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(4-bromo-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(6-bromo-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(7-bromo-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(4,6-dibromo-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(4,7-dibromo-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(6,7-dibromo-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(4-bromo-6-methyl-2,1,3-benzoxadiazole-3-5-yl-1-or-3-N-oxide);

N-(4-bromo-7-methyl-2,1,3-benzoxadiazole-5-yl-1-or-3-N-oxide);

N-(6-bromo-7-methyl-2,1,3-benzoxadiazole-5-yl-1-or-3-N-oxide);

N-(4-methyl-6-bromo-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(4-methyl-7-bromo-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(6-methyl-7-bromo-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(4-bromo-6-ethyl-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(4-bromo-7-ethyl-2,1,3-benzoxadiazole-6-yl-1 - or-3-N-oxide);

N-(6-bromo-7-ethyl-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(4-ethyl-6-bromo-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);
what ID);

N -(4-bromo-6-trifluoromethyl-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(4-bromo-7-trifluoromethyl-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(6-bromo-7-trifluoromethyl-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide;

N-(4-trifluoromethyl-6-bromo-2,1,3-benzoxadiazole-5-yl-1 - or 3-N-oxide;

N-(4-trifluoromethyl-7-bromo-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxid);

N-(6-trifluoromethyl-7-bromo-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide;

N-(4-chloro-2,1,3-benzoxadiazole-5-yl or 3-N-oxide);

N-(6-chloro-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(7-chloro-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(4-nitro-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(6-nitro-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(7-nitro-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(4-bromo-6-tert.-butyl-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(4-bromo-7-tert.-butyl-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(6-bromo-7-tert.-butyl-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(4-tert.-butyl 6-bromo-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(4-tert.-butyl-7-bromo-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(6-tert.-butyl-7-bromo-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(4-chloro-6-methyl-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(4-chloro-7-methyl-2,1,3-benzoxadiazole-5-yl-1 - the ol-5-yl-1 - or-3-N-oxide);

N-(4-methyl-7-chloro-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(6-methyl-7-chloro-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(4-dimethylamino-2,1,3-benzoxadiazole-5-yl-1-or-3-N-oxide);

N-(6-dimethylamino-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(7-dimethylamino-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(4-cyan-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(6-cyan-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(7-cyan-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(4-methoxycarbonyl-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(6-methoxycarbonyl-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(7-methoxycarbonyl-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(4-etoxycarbonyl-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(6-etoxycarbonyl-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(7-etoxycarbonyl-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(4-atsetamino-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(6-acetamido-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

N-(7-acetamido-2,1,3-benzoxadiazole-5-yl-1 - or-3-N-oxide);

with triethylphosphite receive the following 5-dimethylamino-mZ-1 - naphthalenesulfonate, where mZ denotes:

N-(4-methyl-2,1,3-benzoxadiazole-5-yl);

N-(6-methyl-2,1,3-benzoxadiazole-5-yl);

N-(7-met);

N-(6,7-dimethyl-2,1,3-benzoxadiazole-5-yl);

N-(4-trifluoromethyl-2,1,3-benzoxadiazole-5-yl);

N-(6-trifluoromethyl-2,1,3-benzoxadiazole-5-yl);

N-(7-trifluoromethyl-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-2,1,3-benzoxadiazole-5-yl);

N-(6-bromo-2,1,3-benzoxadiazole-5-yl);

N-(7-bromo-2,1,3-benzoxadiazole-5-yl);

N-(4,6-dibromo-2,1,3-benzoxadiazole-5-yl);

N-(4,7-dibromo-2,1,3-benzoxadiazole-5-yl);

N-(6,7-dibromo-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-6-methyl-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-7-methyl-2,1,3-benzoxadiazole-5-yl);

N-(6-bromo-7-methyl-2,1,3-benzoxadiazole-5-yl);

N-(4-methyl-6-bromo-2,1,3-benzoxadiazole-5-yl);

N-(4-methyl-7-bromo-2,1,3-benzoxadiazole-5-yl);

N-(6-methyl-7-bromo-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-6-ethyl-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-7-ethyl-2,1,3-benzoxadiazole-5-yl);

N-(6-bromo-7-ethyl-2,1,3-benzoxadiazole-5-yl);

N-(4-ethyl-6-bromo-2,1,3-benzoxadiazole-5-yl);

N-(4-ethyl-7-bromo-2,1,3-benzoxadiazole-5-yl);

N-(6-ethyl-7-bromo-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-6-trifluoromethyl-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-7-trifluoromethyl-2,1,3-benzoxadiazole-5-yl);

N-(6-bromo-7-trifluoromethyl-2,1,3-benzoxadiazole-5-yl);

N-(4-trifluoromethyl-6-bromo-2,1,3-benzoxadiazole-5-yl);

N-(4-trifluoromethyl-7-bromo-2,1,3-benzoxadiazole the-2,1,3-benzoxadiazole-5-yl);

N-(7-chloro-2,1,3-benzoxadiazole-5-yl);

N-(4-nitro-2,1,3-benzoxadiazole-5-yl);

N-(6-nitro-2,1,3-benzoxadiazole-5-yl);

N-(7-nitro-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-6-tert.-butyl-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-7-tert.-butyl-2,1,3-benzoxadiazole-5-yl);

N-(6-bromo-7-tert.-butyl-2,1,3-benzoxadiazole-5-yl);

N-(4-tert.-butyl 6-bromo-2,1,3-benzoxadiazole-5-yl);

N-(4-tert.-butyl-7-bromo-2,1,3-benzoxadiazole-5-yl);

N-(6-tert.-butyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-chloro-6-methyl-2,1,3-benzoxadiazole-5-yl);

N-(4-chloro-7-methyl-2,1,3-benzoxadiazole-5-yl);

N-(6-chloro-7-methyl-2,1,3-benzoxadiazole-5-yl);

N-(4-methyl-6-chloro-2,1,3-benzoxadiazole-5-yl);

N-(4-methyl-7-chloro-2,1,3-benzoxadiazole-5-yl);

N-(6-methyl-7-chloro-2,1,3-benzoxadiazole-5-yl);

N-(4-dimethylamino-2,1,3-benzoxadiazole-5-yl);

N-(6-dimethylamino-2,1,3-benzoxadiazole-5-yl);

N-(7-dimethylamino-2,1,3-benzoxadiazole-5-yl);

N-(4-cyan-2,1,3-benzoxadiazole-5-yl);

N-(6-cyan-2,1,3-benzoxadiazole-5-yl);

N-(7-cyan-2,1,3-benzoxadiazole-5-yl);

N-(4-methoxycarbonyl-2,1,3-benzoxadiazole-5-yl);

N-(6-methoxycarbonyl-2,1,3-benzoxadiazole-5-yl);

N-(7-methoxycarbonyl-2,1,3-benzoxadiazole-5-yl);

N-(4-etoxycarbonyl-2,1,3-benzoxadiazole-5-yl);

N-(6-etoxycarbonyl-2,1,3-b is on);

N-(6-acetamido-2,1,3-benzoxadiazole-5-yl);

N-(7-acetamido-2,1,3-benzoxadiazole-5-yl).

Example 4

A solution of 1 g of 3-nitro-N-(2,1,3-benzothiadiazole-5-yl)-1 - benzene-sulfonamida in 25 ml of methanol hydronaut at normal pressure and 20oC in the presence of 1 g of Raney Nickel until the termination of the reaction. Filtered off, the solvent is evaporated and get 3-amino-N-(2,1,3-benzothiadiazole-5-yl)-1-benzosulfimide.

Similarly, from

4-nitro-N-(2,1,3-benzothiadiazole-5-yl)-1-benzosulfimide;

2-nitro-5-methyl-N-(2,1,3-benzothiadiazole-5-yl)-1-benzosulfimide;

2-methyl-5-nitro-N-(2,1,3-benzothiadiazole-5-yl)-1-benzosulfimide;

4-nitro-N-(2,1,3-benzoxadiazole-5-yl)-1-benzosulfimide;

3-nitro-N-(2,1,3-benzoxadiazole-5-yl)-1-benzosulfimide;

2-nitro-5-methyl-N-(2,1,3-benzoxadiazole-5-yl)-1-benzosulfimide;

2-methyl-5-nitro-N-(2,1,3-benzoxadiazole-5-yl)-1-benzosulfimide

receive the following connections:

4-amino-N-(2,1,3-benzothiadiazole-5-yl)-1-benzosulfimide;

2-amino-5-methyl-N-(2,1,3-benzothiadiazole-5-yl)-1-benzosulfimide;

2-amino-5-nitro-N-(2,1,3-benzothiadiazole-5-yl)-1-benzosulfimide;

4-amino-N-(2,1,3-benzoxadiazole-5-yl)-1-benzosulfimide;

3-amino-N-(2,1,3-b is R> 2-methyl-5-amino-N-(2,1,3-benzoxadiazole-5-yl)-1-benzosulfimide.

Example 5

Analogously to example 1, by reacting 5-amino-2,1,3 - benzoxadiazole (produced by recovery of 5-nitro - 2,1,3-benzoxadiazole-1 - or-3-N-oxide using triethylphosphite) 2-ethylbenzaldehyde get 2-ethyl-N-(2,1,3-benzoxadiazole-5-yl)-1-benzosulfimide.

Similarly, from 5-amino-mZ-2,1,3-benzoxadiazole, where mZ denotes:

4-methyl; 6-methyl; 7-methyl; 4,6-dimethyl; 4,7-dimethyl; 6,7-dimethyl; 4-trifluoromethyl; 6-trifluoromethyl; 7-trifluoromethyl, 4-bromo, 6-bromo; 7-bromo; 4,6-dibromo; 4,7-dibromo; 6,7-dibromo; 4-bromo-6-methyl; 4-bromo-7-methyl; 6-bromo-7-methyl; 4-methyl-6-bromo, and 4-methyl-7-bromo; 6-methyl-7-bromo, 4-bromo-6-ethyl; 4-bromo-7-ethyl; 6-bromo-7-ethyl; 4-ethyl-6-bromo, 4-ethyl-7-bromo; 6-ethyl-7-bromo, 4-bromo-6-trifluoromethyl; 4-bromo-7-trifluoromethyl; 6-bromo-7-trifluoromethyl, 4-trifluoromethyl-6-bromo, 4-trifluoromethyl-7-bromo; 6-trifluoromethyl-7-bromo; 4-chloro; 6-chloro; 7 - chloro; 4-nitro group; 6-nitro-group; 7-nitro-group; 4-bromo - 6 - tert. -butyl; 4-bromo-7-tert.-butyl; 6-bromo-7-tert.-butyl; 4-tert. - butyl 6-bromo; 4-tert. -butyl-7-bromo; 6-tert. -butyl-7-bromo; 4 - chloro-6-methyl; 4-chloro-7-methyl; 6-chloro-7-methyl; 4-methyl-6-chloro; 4 - methyl-7-chloro; 6-methyl-7-chloro; 4-dimethylamino-group; 6-dimethyl - amino group; 7-dimethylamino-is carbonyl; 7-etoxycarbonyl; 4-acetamido-group; 6-acetamido group; 7-acetamido group;

by interacting with 2-ethyl-benzosulphochloride get the following 2-ethyl-mZ-1-benzosulfimide, where mZ denotes:

N-(4-methyl-2,1,3-benzoxadiazole-5-yl);

N-(6-methyl-2,1,3-benzoxadiazole-5-yl);

N-(7-methyl-2,1,3-benzoxadiazole-5-yl);

N-(4,6-dimethyl-2,1,3-benzoxadiazole-5-yl);

N-(4,7-dimethyl-2,1,3-benzoxadiazole-5-yl);

N-(6,7-dimethyl-2,1,3-benzoxadiazole-5-yl);

N-(4-trifluoromethyl-2,1,3-benzoxadiazole-5-yl);

N-(6-trifluoromethyl-2,1,3-benzoxadiazole-5-yl);

N-(7-trifluoromethyl-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-2,1,3-benzoxadiazole-5-yl);

N-(6-bromo-2,1,3-benzoxadiazole-5-yl);

N-(7-bromo-2,1,3-benzoxadiazole-5-yl);

N-(4,6-dibromo-2,1,3-benzoxadiazole-5-yl);

N-(4,7-dibromo-2,1,3-benzoxadiazole-5-yl);

N-(6,7-dibromo-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-6-methyl-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-7-methyl-2,1,3-benzoxadiazole-5-yl);

N-(6-bromo-7-methyl-2,1,3-benzoxadiazole-5-yl);

N-(4-methyl-6-bromo-2,1,3-benzoxadiazole-5-yl);

N-(4-methyl-7-bromo-2,1,3-benzoxadiazole-5-yl);

N-(6-methyl-7-bromo-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-6-ethyl-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-7-ethyl-2,1,3-benzoxadiazole-5-yl);

N-(6-bromo-7-ethyl-2,1,3-b
N-(6-ethyl-7-bromo-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-6-trifluoromethyl-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-7-trifluoromethyl-2,1,3-benzoxadiazole-5-yl);

N-(6-bromo-7-trifluoromethyl-2,1,3-benzoxadiazole-5-yl);

N-(4-trifluoromethyl-6-bromo-2,1,3-benzoxadiazole-5-yl);

N-(4-trifluoromethyl-7-bromo-2,1,3-benzoxadiazole-5-yl);

N-(6-trifluoromethyl-7-bromo-2,1,3-benzoxadiazole-5-yl);

N-(4-chloro-2,1,3-benzoxadiazole-5-yl);

N-(6-chloro-2,1,3-benzoxadiazole-5-yl);

N-(7-chloro-2,1,3-benzoxadiazole-5-yl);

N-(4-nitro-2,1,3-benzoxadiazole-5-yl);

N-(6-nitro-2,1,3-benzoxadiazole-5-yl);

N-(7-nitro-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-6-tert.-butyl-2, 1,3-benzoxadiazole-5-yl);

N-(4-bromo-7-tert.-butyl-2,1,3-benzoxadiazole-5-yl);

N-(6-bromo-7-tert.-butyl-2,1,3-benzoxadiazole-5-yl);

N-(4-tert.-butyl 6-bromo-2,1,3-benzoxadiazole-5-yl);

N-(4-tert.-butyl-7-bromo-2,1,3-benzoxadiazole-5-yl);

N-(6-tert.-butyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-chloro-6-methyl-2,1,3-benzoxadiazole-5-yl);

N-(4-chloro-7-methyl-2,1,3-benzoxadiazole-5-yl);

N-(6-chloro-7-methyl-2,1,3-benzoxadiazole-5-yl);

N-(4-methyl-6-chloro-2,1, 3-benzoxadiazole-5-yl);

N-(4-methyl-7-chloro-2,1,3-benzoxadiazole-5-yl);

N-(6-methyl-7-chloro-2,1,3-benzoxadiazole-5-yl);

N-(4-dimethylamino-2,1,3-benzoxadiazole-5-yl);
benzoxadiazole-5-yl);

N-(6-cyan-2,1,3-benzoxadiazole-5-yl);

N-(7-cyan-2,1,3-benzoxadiazole-5-yl);

N-(4-methoxycarbonyl-2,1,3-benzoxadiazole-5-yl);

N-(6-methoxycarbonyl-2,1,3-benzoxadiazole-5-yl);

N-(7-methoxycarbonyl-2,1,3-benzoxadiazole-5-yl);

N-(4-etoxycarbonyl-2,1,3-benzoxadiazole-5-yl);

N-(6-etoxycarbonyl-2,1,3-benzoxadiazole-5-yl);

N-(7-etoxycarbonyl-2,1,3-benzoxadiazole-5-yl);

N-(4-acetamido-2,1,3-benzoxadiazole-5-yl);

N-(6-acetamido-2,1,3-benzoxadiazole-5-yl);

N-(7-acetamido-2,1,3-benzoxadiazole-5-yl).

By appropriate interactions with 2-ethyl-5-bromo-benzene - sulfochloride get the following 2-ethyl-5-bromo-mZ-1-benzene - sulfonamides, where mZ denotes:

N-(4-methyl-2,1,3-benzoxadiazole-5-yl);

N-(6-methyl-2,1,3-benzoxadiazole-5-yl);

N-(7-methyl-2,1,3-benzoxadiazole-5-yl);

N-(4,6-dimethyl-2,1,3-benzoxadiazole-5-yl);

N-(4,7-dimethyl-2,1,3-benzoxadiazole-5-yl);

N-(6,7-dimethyl-2,1,3-benzoxadiazole-5-yl);

N-(4-trifluoromethyl-2,1,3-benzoxadiazole-5-yl);

N-(6-trifluoromethyl-2,1,3-benzoxadiazole-5-yl);

N-(7-trifluoromethyl-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-2,1,3-benzoxadiazole-5-yl);

N-(6-bromo-2,1,3-benzoxadiazole-5-yl);

N-(7-bromo-2,1,3-benzoxadiazole-5-yl);

N-(4,6-dibromo-2,1,3-benzoxadiazole-5-yl);
xavator-5-yl);

N-(4-bromo-7-methyl-2,1,3-benzoxadiazole-5-yl);

N-(6-bromo-7-methyl-2,1,3-benzoxadiazole-5-yl);

N-(4-methyl-6-bromo-2,1,3-benzoxadiazole-5-yl);

N-(4-methyl-7-bromo-2,1,3-benzoxadiazole-5-yl);

N-(6-methyl-7-bromo-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-6-ethyl-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-7-ethyl-2,1,3-benzoxadiazole-5-yl);

N-(6-bromo-7-ethyl-2,1,3-benzoxadiazole-5-yl);

N-(4-ethyl-6-bromo-2,1,3-benzoxadiazole-5-yl);

N-(4-ethyl-7-bromo-2,1,3-benzoxadiazole-5-yl);

N-(6-ethyl-7-bromo-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-6-trifluoromethyl-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-7-trifluoromethyl-2,1,3-benzoxadiazole-5-yl);

N-(6-bromo-7-trifluoromethyl-2,1,3-benzoxadiazole-5-yl);

N-(4-trifluoromethyl-6-bromo-2,1,3-benzoxadiazole-5-yl);

N-(4-trifluoromethyl-7-bromo-2,1,3-benzoxadiazole-5-yl);

N-(6-trifluoromethyl-7-bromo-2,1,3-benzoxadiazole-5-yl);

N-(4-chloro-2,1,3-benzoxadiazole-5-yl);

N-(6-chloro-2,1,3-benzoxadiazole-5-yl);

N-(7-chloro-2,1,3-benzoxadiazole-5-yl);

N-(4-nitro-2,1,3-benzoxadiazole-5-yl);

N-(6-nitro-2,1,3-benzoxadiazole-5-yl);

N-(7-nitro-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-6-tert.-butyl-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-7-tert.-butyl-2,1,3-benzoxadiazole-5-yl);

N-(6-bromo-7-tert.-butyl-2,1,3-benzoxadiazole-5-yl);

N-(4-tert.-butyl-6-b is socializa-5-yl);

N-(4-chloro-6-methyl-2,1,3-benzoxadiazole-5-yl);

N-(4-chloro-7-methyl-2,1,3-benzoxadiazole-5-yl);

N-(6-chloro-7-methyl-2,1,3-benzoxadiazole-5-yl);

N-(4-methyl-6-chloro-2,1,3-benzoxadiazole-5-yl);

N-(4-methyl-7-chloro-2,1,3-benzoxadiazole-5-yl);

N-(6-methyl-7-chloro-2,1,3-benzoxadiazole-5-yl);

N-(4-dimethylamino-2,1,3-benzoxadiazole-5-yl);

N-(6-dimethylamino-2,1,3-benzoxadiazole-5-yl);

N-(7-dimethylamino-2,1,3-benzoxadiazole-5-yl);

N-(4-cyan-2,1,3-benzoxadiazole-5-yl);

N-(6-cyan-2,1,3-benzoxadiazole-5-yl);

N-(7-cyan-2,1,3-benzoxadiazole-5-yl);

N-(4-methoxycarbonyl-2,1,3-benzoxadiazole-5-yl);

N-(6-methoxycarbonyl-2,1,3-benzoxadiazole-5-yl);

N-(7-methoxycarbonyl-2,1,3-benzoxadiazole-5-yl);

N-(4-etoxycarbonyl-2,1,3-benzoxadiazole-5-yl);

N-(6-etoxycarbonyl-2,1,3-benzoxadiazole-5-yl);

N-(7-etoxycarbonyl-2,1,3-benzoxadiazole-5-yl);

N-(4-acetamido-2,1,3-benzoxadiazole-5-yl);

N-(6-acetamido-2,1,3-benzoxadiazole-5-yl);

N-(7-acetamido-2,1,3-benzoxadiazole-5-yl);

and by a similar interaction with 2-propyl-5-bromo - benzosulphochloride get the following 2-propyl-5-bromo-mZ-1-benzosulfimide, where mZ denotes:

N-(4-methyl-2,1,3-benzoxadiazole-5-yl);

N-(6-methyl-2,1,3-benzoxadiazole-5-yl);

N-(7-mate the BR>
N-(6,7-dimethyl-2,1,3-benzoxadiazole-5-yl);

N-(4-trifluoromethyl-2,1,3-benzoxadiazole-5-yl);

N-(6-trifluoromethyl-2,1,3-benzoxadiazole-5-yl);

N-(7-trifluoromethyl-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-2,1,3-benzoxadiazole-5-yl);

N-(6-bromo-2,1,3-benzoxadiazole-5-yl);

N-(7-bromo-2,1,3-benzoxadiazole-5-yl);

N-(4,6-dibromo-2,1,3-benzoxadiazole-5-yl);

N-(4,7-dibromo-2,1,3-benzoxadiazole-5-yl);

N-(6,7-dibromo-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-6-methyl-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-7-methyl-2,1,3-benzoxadiazole-5-yl);

N-(6-bromo-7-methyl-2,1,3-benzoxadiazole-5-yl);

N-(4-methyl-6-bromo-2,1,3-benzoxadiazole-5-yl);

N-(4-methyl-7-bromo-2,1,3-benzoxadiazole-5-yl);

N-(6-methyl-7-bromo-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-6-ethyl-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-7-ethyl-2,1,3-benzoxadiazole-5-yl);

N-(6-bromo-7-ethyl-2,1,3-benzoxadiazole-5-yl);

N-(4-ethyl-6-bromo-2,1,3-benzoxadiazole-5-yl);

N-(4-ethyl-7-bromo-2,1,3-benzoxadiazole-5-yl);

N-(6-ethyl-7-bromo-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-6-trifluoromethyl-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-7-trifluoromethyl-2,1,3-benzoxadiazole-5-yl);

N-(6-bromo-7-trifluoromethyl-2,1,3-benzoxadiazole-5-yl);

N-(4-trifluoromethyl-6-bromo-2,1,3-benzoxadiazole-5-yl);

N-(4-trifluoromethyl-7-bromo-2,1,3-benzoxadiazole the-2,1,3-benzoxadiazole-5-yl);

N-(7-chloro-2,1,3-benzoxadiazole-5-yl);

N-(4-nitro-2,1,3-benzoxadiazole-5-yl);

N-(6-nitro-2,1,3-benzoxadiazole-5-yl);

N-(7-nitro-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-6-tert.-butyl-2,1,3-benzoxadiazole-5-yl);

N-(4-bromo-7-tert.-butyl-2,1,3-benzoxadiazole-5-yl);

N-(6-bromo-7-tert.-butyl-2,1,3-benzoxadiazole-5-yl);

N-(4-tert.-butyl 6-bromo-2, 1,3-benzoxadiazole-5-yl);

N-(4-tert.-butyl-7-bromo-2,1,3-benzoxadiazole-5-yl);

N-(6-tert.-butyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-chloro-6-methyl-2,1,3-benzoxadiazole-5-yl);

N-(4-chloro-7-methyl-2,1,3-benzoxadiazole-5-yl);

N-(6-chloro-7-methyl-2,1,3-benzoxadiazole-5-yl);

N-(4-methyl-6-chloro-2,1,3-benzoxadiazole-5-yl);

N-(4-methyl-7-chloro-2,1,3-benzoxadiazole-5-yl);

N-(6-methyl-7-chloro-2,1,3-benzoxadiazole-5-yl);

N-(4-dimethylamino-2,1,3-benzoxadiazole-5-yl);

N-(6-dimethylamino-2,1,3-benzoxadiazole-5-yl);

N-(7-dimethylamino-2,1,3-benzoxadiazole-5-yl);

N-(4-cyan-2,1,3-benzoxadiazole-5-yl);

N-(6-cyan-2,1,3-benzoxadiazole-5-yl);

N-(7-cyan-2,1,3-benzoxadiazole-5-yl);

N-(4-methoxycarbonyl-2,1,3-benzoxadiazole-5-yl);

N-(6-methoxycarbonyl-2,1,3-benzoxadiazole-5-yl);

N-(7-methoxycarbonyl-2,1,3-benzoxadiazole-5-yl);

N-(4-etoxycarbonyl-2,1,3-benzoxadiazole-5-yl);

N-(6-etoxycarbonyl-2,1,3-b is on);

N-(6-acetamido-2,1,3-benzoxadiazole-5-yl);

N-(7-acetamido-2,1,3-benzoxadiazole-5-yl).

Similarly, from 5-amino-mZ-2,1,3-benzothiadiazole, where mZ denotes:

4-methyl; 6-methyl; 7-methyl; 4,6-dimethyl; 4,7-dimethyl; 6,7-dimethyl; 4-trifluoromethyl; 6-trifluoromethyl; 7-trifluoromethyl, 4-bromo, 6-bromo; 7-bromo; 4,6-dibromo; 4,7-dibromo; 6,7-dibromo; 4-bromo-6-methyl; 4-bromo-7-methyl; 6-bromo-7-methyl; 4-methyl-6-bromo, and 4-methyl-7-bromo; 6-methyl-7-bromo, 4-bromo-6-ethyl; 4-bromo-7-ethyl; 6-bromo-7-ethyl; 4-ethyl-6-bromo, 4-ethyl-7-bromo; 6-ethyl-7-bromo, 4-bromo-6-trifluoromethyl; 4-bromo 7-trifluoromethyl; 6-bromo-7-trifluoromethyl, 4-trifluoromethyl-6-bromo, 4-trifluoromethyl-7-bromo; 6-trifluoromethyl-7-bromo; 4-chloro; 6-chloro; 7-chloro; 4-nitro group; 6 - nitro-group; 7-nitro-group; 4-bromo - 6-tert. -butyl; 4-bromo-7-tert.-butyl; 6-bromo-7-tert.-butyl; 4-tert. -butyl 6-bromo; 4-tert. -butyl-7-bromo; 6-tert. -butyl-7-bromo; 4-chloro-6-methyl; 4-chloro-7-methyl; 6-chloro-7-methyl; 4-methyl-6-chloro; 4-methyl-7-chloro; 6-methyl-7-chloro; 4-dimethylamino-group; 6-dimethylamino group; 7-dimethylamino-group; 4-cyan; 6-cyan; 7-cyan; 4-methoxycarbonyl; 6-methoxycarbonyl; 7-methoxycarbonyl; 4-etoxycarbonyl; 6-etoxycarbonyl; 7-etoxycarbonyl; 4-acetamido-group; 6-acetamido group; 7-acetamido group;

by entering into interaction with 2-ethyl-benzosulphochloride R>N-(6-methyl-2,1,3-benzothiadiazole-5-yl);

N-(7-methyl-2,1,3-benzothiadiazole-5-yl);

N-(4,6-dimethyl-2,1,3-benzothiadiazole-5-yl);

N-(4,7-dimethyl-2,1,3-benzothiadiazole-5-yl);

N-(6,7-dimethyl-2,1,3-benzothiadiazole-5-yl);

N-(4-trifluoromethyl-2,1,3-benzothiadiazole-5-yl);

N-(6-trifluoromethyl-2,1,3-benzothiadiazole-5-yl);

N-(7-trifluoromethyl-2,1,3-benzothiadiazole-5-yl);

N-(4-bromo-2,1,3-benzothiadiazole-5-yl);

N-(6-bromo-2,1,3-benzothiadiazole-5-yl);

N-(7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4,6-dibromo-2,1,3-benzothiadiazole-5-yl);

N-(4,7-dibromo-2,1,3-benzothiadiazole-5-yl);

N-(6,7-dibromo-2,1,3-benzothiadiazole-5-yl);

N-(4-bromo-6-methyl-2,1,3-benzothiadiazole-5-yl);

N-(4-bromo-7-methyl-2,1,3-benzothiadiazole-5-yl);

N-(6-bromo-7-methyl-2,1,3-benzothiadiazole-5-yl);

N-(4-methyl-6-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-methyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(6-methyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-bromo-6-ethyl-2,1,3-benzothiadiazole-5-yl);

N-(4-bromo-7-ethyl-2,1,3-benzothiadiazole-5-yl);

N-(6-bromo-7-ethyl-2,1,3-benzothiadiazole-5-yl);

N-(4-ethyl-6-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-ethyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(6-ethyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-bromo-6-trifluoromethyl-2,1,3-benzothiadiazole-5-yl);

N-(4-bromo-7-trifluoromethyl-2,1,3-benzothiadiazin the l);

N-(4-trifluoromethyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(6-trifluoromethyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-chloro-2,1,3-benzothiadiazole-5-yl);

N-(6-chloro-2,1,3-benzothiadiazole-5-yl);

N-(7-chloro-2,1,3-benzothiadiazole-5-yl);

N-(4-nitro-2,1,3-benzothiadiazole-5-yl);

N-(6-nitro-2,1,3-benzothiadiazole-5-yl);

N-(7-nitro-2,1,3-benzothiadiazole-5-yl);

N-(4-bromo-6-tert.-butyl-2,1,3-benzothiadiazole-5-yl);

N-(4-bromo-7-tert.-butyl-2,1,3-benzothiadiazole-5-yl);

N-(6-bromo-7-tert.-butyl-2,1,3-benzothiadiazole-5-yl);

N-(4-tert.-butyl 6-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-tert.-butyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(6-tert.-butyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-chloro-6-methyl-2,1,3-benzothiadiazole-5-yl);

N-(4-chloro-7-methyl-2,1,3-benzothiadiazole-5-yl);

N-(6-chloro-7-methyl-2,1,3-benzothiadiazole-5-yl);

N-(4-methyl-6-chloro-2,1, 3-benzothiadiazole-5-yl);

N-(4-methyl-7-chloro-2,1,3-benzothiadiazole-5-yl);

N-(6-methyl-7-chloro-2,1,3-benzothiadiazole-5-yl);

N-(4-dimethylamino-2,1,3-benzothiadiazole-5-yl);

N-(6-dimethylamino-2,1,3-benzothiadiazole-5-yl);

N-(7-dimethylamino-2,1,3-benzothiadiazole-5-yl);

N-(4-cyan-2,1,3-benzothiadiazole-5-yl);

N-(6-cyan-2,1,3-benzothiadiazole-5-yl);

N-(7-cyan-2,1,3-benzothiadiazole-5-yl);

N-(4-methoxycarbonyl-2,1,3-benzothiadiazole-5-and the 4-etoxycarbonyl-2,1,3-benzothiadiazole-5-yl);

N-(6-etoxycarbonyl-2,1,3-benzothiadiazole-5-yl);

N-(7-etoxycarbonyl-2,1,3-benzothiadiazole-5-yl);

N-(4-acetamido-2,1,3-benzothiadiazole-5-yl);

N-(6-acetamido-2,1,3-benzothiadiazole-5-yl);

N-(7-acetamido-2,1,3-benzothiadiazole-5-yl);

and by a similar interaction with 2-ethyl-5-bromo - benzosulphochloride get the following 2-ethyl-5-bromo-mZ-1 - benzosulfimide, where mZ denotes:

N-(4-methyl-2,1,3-benzothiadiazole-5-yl);

N-(6-methyl-2,1,3-benzothiadiazole-5-yl);

N-(7-methyl-2,1,3-benzothiadiazole-5-yl);

N-(4,6-dimethyl-2,1,3-benzothiadiazole-5-yl);

N-(4,7-dimethyl-2,1,3-benzothiadiazole-5-yl);

N-(6,7-dimethyl-2,1,3-benzothiadiazole-5-yl);

N-(4-trifluoromethyl-2,1,3-benzothiadiazole-5-yl);

N-(6-trifluoromethyl-2,1,3-benzothiadiazole-5-yl);

N-(7-trifluoromethyl-2,1,3-benzothiadiazole-5-yl);

N-(4-bromo-2,1,3-benzothiadiazole-5-yl);

N-(6-bromo-2,1,3-benzothiadiazole-5-yl);

N-(7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4,6-dibromo-2,1,3-benzothiadiazole-5-yl);

N-(4,7-dibromo-2,1,3-benzothiadiazole-5-yl);

N-(6,7-dibromo-2,1,3-benzothiadiazole-5-yl);

N-(4-bromo-6-methyl-2,1, 3-benzothiadiazole-5-yl);

N-(4-bromo-7-methyl-2,1,3-benzothiadiazole-5-yl);

N-(6-bromo-7-methyl-2,1,3-benzothiadiazole-5-yl);

N-(4-methyl-6-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-methyl-7-the ol-5-yl);

N-(4-bromo-7-ethyl-2,1,3-benzothiadiazole-5-yl);

N-(6-bromo-7-ethyl-2,1,3-benzothiadiazole-5-yl);

N-(4-ethyl-6-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-ethyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(6-ethyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-bromo-6-trifluoromethyl-2,1,3-benzothiadiazole-5-yl);

N-(4-bromo-7-trifluoromethyl-2,1,3-benzothiadiazole-5-yl);

N-(6-bromo-7-trifluoromethyl-2,1,3-benzothiadiazole-5-yl);

N-(4-trifluoromethyl-6-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-trifluoromethyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(6-trifluoromethyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-chloro-2,1,3-benzothiadiazole-5-yl);

N-(6-chloro-2,1,3-benzothiadiazole-5-yl);

N-(7-chloro-2,1,3-benzothiadiazole-5-yl);

N-(4-nitro-2,1,3-benzothiadiazole-5-yl);

N-(6-nitro-2,1,3-benzothiadiazole-5-yl);

N-(7-nitro-2,1,3-benzothiadiazole-5-yl);

N-(4-bromo-7-tert.-butyl-2,1,3-benzothiadiazole-5-yl);

N-(4-bromo-7-tert.-butyl-2,1,3-benzothiadiazole-5-yl);

N-(6-bromo-7-tert.-butyl-2,1,3-benzothiadiazole-5-yl);

N-(4-tert.-butyl 6-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-tert.-butyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(6-tert.-butyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-chloro-6-methyl-2,1,3-benzothiadiazole-5-yl);

N-(4-chloro-7-methyl-2,1,3-benzothiadiazole-5-yl);

N-(6-chloro-7-methyl-2,1,3-benzothiadiazole-5-yl);

isothiazol-5-yl);

N-(4-dimethylamino-2,1,3-benzothiadiazole-5-yl);

N-(6-dimethylamino-2,1,3-benzothiadiazole-5-yl);

N-(7-dimethylamino-2,1,3-benzothiadiazole-5-yl);

N-(4-cyan-2,1,3-benzothiadiazole-5-yl);

N-(6-cyan-2,1,3-benzothiadiazole-5-yl);

N-(7-cyan-2,1,3-benzothiadiazole-5-yl);

N-(4-methoxycarbonyl-2,1,3-benzothiadiazole-5-yl);

N-(6-methoxycarbonyl-2,1,3-benzothiadiazole-5-yl);

N-(7-methoxycarbonyl-2,1,3-benzothiadiazole-5-yl);

N-(4-etoxycarbonyl-2,1,3-benzothiadiazole-5-yl);

N-(6-etoxycarbonyl-2,1,3-benzothiadiazole-5-yl);

N-(7-etoxycarbonyl-2,1,3-benzothiadiazole-5-yl);

N-(4-acetamido-2,1,3-benzothiadiazole-5-yl);

N-(6-acetamido-2,1,3-benzothiadiazole-5-yl);

N-(7-acetamido-2,1,3-benzothiadiazole-5-yl);

also, by similar interactions with 2-propyl-5-bromo - benzosulphochloride get the following 2-propyl-5-bromo-mZ-1-benzosulfimide, where mZ denotes:

N-(4-methyl-2,1,3-benzothiadiazole-5-yl);

N-(6-methyl-2,1,3-benzothiadiazole-5-yl);

N-(7-methyl-2,1,3-benzothiadiazole-5-yl);

N-(4,6-dimethyl-2,1,3-benzothiadiazole-5-yl);

N-(4,7-dimethyl-2,1,3-benzothiadiazole-5-yl);

N-(6,7-dimethyl-2,1,3-benzothiadiazole-5-yl);

N-(4-trifluoromethyl-2,1,3-benzothiadiazole-5-yl);

N-(6-trifluoromethyl-2,1,3-benzothiadiazole-5-yl);

N-(7-cryptomate the bromo-2,1,3-benzothiadiazole-5-yl);

N-(4,6-dibromo-2,1,3-benzothiadiazole-5-yl);

N-(4,7-dibromo-2,1,3-benzothiadiazole-5-yl);

N-(6,7-dibromo-2,1,3-benzothiadiazole-5-yl);

N-(4-bromo-6-methyl-2,1,3-benzothiadiazole-5-yl);

N-(4-bromo-7-methyl-2,1,3-benzothiadiazole-5-yl);

N-(6-bromo-7-methyl-2,1,3-benzothiadiazole-5-yl);

N-(4-methyl-6-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-methyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(6-methyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-bromo-6-ethyl-2,1,3-benzothiadiazole-5-yl);

N-(4-bromo-7-ethyl-2,1,3-benzothiadiazole-5-yl);

N-(6-bromo-7-ethyl-2,1,3-benzothiadiazole-5-yl);

N-(4-ethyl-6-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-ethyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(6-ethyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-bromo-6-trifluoromethyl-2,1,3-benzothiadiazole-5-yl);

N-(4-bromo-7-trifluoromethyl-2,1,3-benzothiadiazole-5-yl);

N-(6-bromo-7-trifluoromethyl-2,1,3-benzothiadiazole-5-yl);

N-(4-trifluoromethyl-6-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-trifluoromethyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(6-trifluoromethyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-chloro-2,1,3-benzothiadiazole-5-yl);

N-(6-chloro-2,1,3-benzothiadiazole-5-yl);

N-(7-chloro-2,1,3-benzothiadiazole-5-yl);

N-(4-nitro-2,1,3-benzothiadiazole-5-yl);

N-(6-nitro-2,1,3-benzothiadiazole-5-yl);

N-(7-nitro-2,1,3-benzothiadiazole-5-yl);

tert.-butyl-2,1,3-benzothiadiazole-5-yl);

N-(4-tert.-butyl 6-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-tert.-butyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(6-tert.-butyl-7-bromo-2,1,3-benzothiadiazole-5-yl);

N-(4-chloro-6-methyl-2,1,3-benzothiadiazole-5-yl);

N-(4-chloro-7-methyl-2,1,3-benzothiadiazole-5-yl);

N-(6-chloro-7-methyl-2,1,3-benzothiadiazole-5-yl);

N-(4-methyl-6-chloro-2,1,3-benzothiadiazole-5-yl);

N-(4-methyl-7-chloro-2,1,3-benzothiadiazole-5-yl);

N-(6-methyl-7-chloro-2,1,3-benzothiadiazole-5-yl);

N-(4-dimethylamino-2,1,3-benzothiadiazole-5-yl);

N-(6-dimethylamino-2,1,3-benzothiadiazole-5-yl);

N-(7-dimethylamino-2,1,3-benzothiadiazole-5-yl);

N-(4-cyan-2,1,3-benzothiadiazole-5-yl);

N-(6-cyan-2,1,3-benzothiadiazole-5-yl);

N-(7-cyan-2,1,3-benzothiadiazole-5-yl);

N-(4-methoxycarbonyl-2,1,3-benzothiadiazole-5-yl);

N-(6-methoxycarbonyl-2,1,3-benzothiadiazole-5-yl);

N-(7-methoxycarbonyl-2,1,3-benzothiadiazole-5-yl);

N-(4-etoxycarbonyl-2,1,3-benzothiadiazole-5-yl);

N-(6-etoxycarbonyl-2,1,3-benzothiadiazole-5-yl);

N-(7-etoxycarbonyl-2,1,3-benzothiadiazole-5-yl);

N-(4-acetamido-2,1,3-benzothiadiazole-5-yl);

N-(6-acetamido-2,1,3-benzothiadiazole-5-yl);

N-(7-acetamido-2,1,3-benzothiadiazole-5-yl).

Example 6

Analogously to example 1, by introducing into the interaction of 6 - amino-1, 2, 5-oxadiazole/3,4 Similarly, of the following mZ-6-amino-1,2,5-oxadiazole- (3,4-b)-pyridines, where mZ denotes:

5-methyl; 7-methyl; 5,7-dimethyl; 5-trifluoromethyl; 7-trifluoromethyl; 5 - bromo; 7-bromo; 5,7-dibromo; 5-bromo-7-methyl; 5-methyl-7-bromo, 5-bromo-7-ethyl; 5-ethyl-7-bromo, 5-bromo-7-trifluoromethyl; 5-trifluoromethyl-7 - bromo; 5-chloro; 7-chloro, 5-nitro-group; 7-nitro group; 5-bromo-7 - tert. -butyl; 5-tert.-butyl-7-bromo; 5-chloro-7-methyl; 5-methyl-7-chloro; 5-dimethylamino group; 7-dimethylamino group; 5-cyan; 7-cyan; 5 - methoxycarbonyl; 7-methoxycarbonyl; 5-etoxycarbonyl; 7 ethoxy - carbonyl; 5-atsetamino group; 7-ndimethylacetamide;

by interacting with "A" will receive the following 5-dimethyl-amino-N-(mZ-1,2 5-oxadiazole/3,4-b/pyridine-6-yl) -1-naphthalenesulfonate, where wZ denotes:

5-methyl; 7-methyl; 5,7-dimethyl; 5-trifluoromethyl; 7 - trifluoromethyl; 5-bromo; 7-bromo; 5,7-dibromo; 5-bromo-7-methyl; 5-methyl - 7-bromo, 5-bromo-7-ethyl; 5-ethyl-7-bromo, 5-bromo-7-trifluoromethyl; 5 - trifluoromethyl-7-bromo; 5-chloro; 7-chloro, 5-nitro-group; 7-nitro group; 5-bromo-7-tert.-butyl; 5-tert.-butyl-7-bromo; 5-chloro-7 - methyl; 5-methyl-7-chloro; 5-dimethylamino group; 7-dimethylamino group; 5-cyan; 7-cyan; 5-methoxycarbonyl; 7-methoxycarbonyl; 5-etoxycarbonyl; 7 ethoxy-carbonyl; 5-acetamido-group; 7-acetamido group.

Similarly, by reacting 6-amino-1,2,5 - ti is SS="ptx2">

Similarly, of the following mZ-6-amino-1,2, 5-thiadiazolo-/3,4-b/-pyridines, where mZ denotes:

5-methyl; 7-methyl; 5,7-dimethyl; 5-trifluoromethyl; 7-trifluoromethyl; 5 - bromo; 7-bromo; 5,7-dibromo; 5-bromo-7-methyl; 5-methyl-7-bromo, 5-bromo - 7-ethyl; 5-ethyl-7-bromo, 5-bromo-7-trifluoromethyl; 5-Cryptor-methyl-7 - bromo; 5-chloro; 7-chloro, 5-nitro-group; 7-nitro -; 5-bromo-7 - tert.-butyl; 5-tert.-butyl-7-bromo; 5-chloro-7-methyl; 5-methyl-7 - chloro; 5-dimethylamino group; 7-dimethylamino group; 5-cyan; 7 - cyan; 5-methoxycarbonyl; 7-methoxycarbonyl; 5-etoxycarbonyl; 7 - etoxycarbonyl; 5-acetamido-group; 7-acetamido group;

by interacting with "A" will receive the following 5-dimethyl-amino-N-(mZ-1,2,5-thiadiazolo-/3,4-b/-pyridine-6-yl)-1-naphthalenesulfonate, where mZ denotes:

5-methyl, T. pl. 192oC; 7-methyl; 5,7-dimethyl; 5-trifluoromethyl; 7-trifluoromethyl; 5-bromo; 7-bromo; 5,7-dibromo; 5-bromo-7-methyl; 5-methyl-7-bromo, 5-bromo-7-ethyl; 5-ethyl-7-bromo, 5-bromo-7-trifluoromethyl; 5-trifluoromethyl-7-bromo; 5-chloro; 7-chloro, 5-nitro-group; 7-nitro group; 5-bromo-7-tert.-butyl; 5-tert.-butyl-7-bromo; 5-chloro-7-methyl; 5-methyl-7-chloro; 5-dimethylamino group; 7-dimethylamino group; 5-cyan; 7-cyan; 5-methoxycarbonyl; 7-methoxycarbonyl; 5-ethoxy-carbonyl; 7-etoxycarbonyl; 5-acetamido-group; 7-acetamido group.

Similar to the olo-/3,4-b/-5-yl)-1-naphthalenesulfonate.

Similarly, by reacting 7-amino-1,2,5-oxadiazole/3,4-b/pyridine with "And" receive 5-dimethylamino-N- (1,2,5-oxadiazol-/3,4-b/pyridine-7-yl)-1-naphthalenesulfonate

Similarly, of the following mZ-7-amino - 1,2,5-oxadiazole-/3,4-b/-pyridines, where mZ denotes:

5-methyl; 6-methyl; 5,6-dimethyl, 5-trifluoromethyl, 6-trifluoromethyl; 5-bromo, 6-bromo; 5,6-dibromo; 5-bromo-6-methyl; 5-methyl-6-bromo, 5-bromo-6-ethyl; 5-ethyl-6-bromo, 5-bromo-6-trifluoromethyl; 5-trifluoromethyl-6-bromo; 5-chloro; 6-chloro, 5-nitro-group; 6-nitro-group; 5-bromo-6-tert. -butyl; 5-tert.-butyl 6-bromo; 5-chloro-6-methyl; 5-methyl-6-chloro; 5-dimethylamino group; 6-dimethylamino group; 5-cyan 6-cyan; 5 - methoxycarbonyl; 6-methoxycarbonyl; 5-etoxycarbonyl; 6 ethoxy-carbonyl; 5-acetamido-group; 6-acetamido-group;

by interacting with "A" will receive the following 5-dimethyl-amino-N-(mZ-1,2,5-oxadiazole/3,4-b/pyridine-6-yl) -1-naphthalenesulfonate, where mZ denotes:

5-methyl; 6-methyl; 5,6-dimethyl, 5-trifluoromethyl, 6-trifluoromethyl; 5-bromo, 6-bromo; 5,6-dibromo; 5-bromo-6-methyl; 5-methyl-6-bromo, 5-bromo-6-ethyl; 5-ethyl-6-bromo, 5-bromo-6-trifluoromethyl; 5-trifluoromethyl-6-bromo; 5-chloro; 6-chloro, 5-nitro-group; 6-nitro-group; 5-bromo-6-tert. -butyl; 5-tert.-butyl 6-bromo; 5-chloro-6-methyl; 5-methyl-6-chloro; 5-dimethylamino group; 6 - dimetilan the group; 6-acetamido-group.

Similarly, by reacting 7-amino-1,2,5-thiadiazolo/3,4-b/pyridine with "And" receive 5-dimethylamino-N-(1,2,5-thiadiazolo-/3,4-b/-pyridin-7-yl) -1-naphthalenesulfonate.

Similarly, of the following mZ-7-amino-1,2,5 - thiadiazolo-/3,4-b/pyridines, where mZ denotes:

5-methyl; 6-methyl; 5,6-dimethyl, 5-trifluoromethyl, 6-trifluoromethyl; 5-bromo, 6-bromo; 5,6-dibromo; 5-bromo-6-methyl; 5-methyl-6-bromo, 5-bromo-6-ethyl; 5-ethyl-6-bromo, 5-bromo-6-trifluoromethyl; 5-trifluoromethyl-6-bromo; 5-chloro; 6-chloro, 5-nitro-group; 6-nitro-group; 5-bromo-6-tert. -butyl; 5-tert.-butyl 6-bromo; 5-chloro-6-methyl; 5-methyl-6-chloro; 5-dimethylamino group; 6-dimethylamino group; 5-cyan 6-cyan; 5-methoxycarbonyl; 6-methoxycarbonyl; 5-etoxycarbonyl; 6 ethoxy-carbonyl; 5-acetamido-group; 6-acetamido-group;

by interacting with "A" will receive the following 5-dimethylamino-N-(mZ-1,2,5-thiadiazolo/3,4-b/pyridine-6-yl)-1 - naphthalenesulfonate, where mZ denotes:

5-methyl; 6-methyl; 5,6-dimethyl, 5-trifluoromethyl, 6-trifluoromethyl; 5-bromo, 6-bromo; 5,6-dibromo; 5-bromo-6-methyl; 5-methyl-6-bromo, 5-bromo-6-ethyl; 5-ethyl-6-bromo, 5-bromo-6-trifluoromethyl; 5-trifluoromethyl-6-bromo; 5-chloro; 6-chloro, 5-nitro-group; 6-nitro-group; 5-bromo-6-tert. -butyl; 5-tert.-butyl 6-bromo; 5-chloro-6-methyl; 5-methyl-6-chloro; 5-dimethylcarbinol; 5-acetamido-group; 6-acetamido-group.

Example 7

Analogously to example 1, by reacting 4-amino-2,1,3 - benzoxadiazole with "And" receive 5-dimethylamino-N-(2,1,3 - benzoxadiazole-4-yl)-1-naphthalenesulfonate;

and of the following 4-amino-mZ-2,1,3-benzoxadiazole, where mZ denotes:

5-methyl; 6-methyl; 7-methyl; 5,6-dimethyl; 5,7-dimethyl; 6,7 - dimethyl; 5-trifluoromethyl; 6-trifluoromethyl; 7-trifluoromethyl; 5-bromo, 6-bromo; 7-bromo; 5,6-dibromo; 5,7-dibromo; 6,7-dibromo; 5-bromo-6 - methyl; 5-bromo-7-methyl; 6-bromo-7-methyl; 5-methyl-6-bromo; 5-methyl-7 - bromo; 6-methyl-7-bromo, 5-bromo-6-ethyl; 5-bromo-7-ethyl; 6-bromo-7 - ethyl; 5-ethyl-6-bromo; 5-ethyl-7-bromo; 6-ethyl-7-bromo, 5-bromo-6 - trifluoromethyl; 5-bromo-7-trifluoromethyl; 6-bromo-7-trifluoromethyl; 5 - trifluoromethyl-6-bromo, 5-trifluoromethyl-7-bromo; 6-trifluoromethyl-7-bromo; 5-chloro; 6-chloro; 7-chloro, 5-nitro-group; 6-nitro-group; 7-nitro -; 5-bromo-6-tert. -butyl; 5-bromo-7-tert.-butyl; 6-bromo-7 - tert.-butyl; 5-tert.- butyl 6-bromo; 5-tert. -butyl-7-bromo; 6-tert. - butyl-7-bromo; 5-chloro-6-methyl; 5-chloro-7-methyl; 6-chloro-7-methyl; 5 - methyl-6-chloro; 5-methyl-7-chloro; 6-methyl-7-chloro; 5-dimethylamino group; 6-dimethylamino group; 7-dimethylamino group; 5-cyan 6 - cyan; 7-cyan; 5-methoxycarbonyl; 6-methoxycarbonyl; 7 - methoxycarbonyl; 5-etoxycarbonyl; 6-etoxycarbonyl; 7 - etoxycarbonyl; 5-acetamido-g - amino-mZ-1-naphthalenesulfonate, where mZ denotes:

N-(5-methyl-2,1,3-benzoxadiazole-4-yl);

N-(6-methyl-2,1,3-benzoxadiazole-4-yl);

N-(7-methyl-2,1,3-benzoxadiazole-4-yl);

N-(5,6-dimethyl-2,1,3-benzoxadiazole-4-yl);

N-(5,7-dimethyl-2,1,3-benzoxadiazole-4-yl);

N-(6,7-dimethyl-2,1,3-benzoxadiazole-4-yl);

N-(5-trifluoromethyl-2,1,3-benzoxadiazole-4-yl);

N-(6-trifluoromethyl-2,1,3-benzoxadiazole-4-yl);

N-(7-trifluoromethyl-2,1,3-benzoxadiazole-4-yl);

N-(5-bromo-2,1,3-benzoxadiazole-4-yl);

N-(6-bromo-2,1,3-benzoxadiazole-4-yl);

N-(7-bromo-2,1,3-benzoxadiazole-4-yl);

N-(5,6-dibromo-2,1,3-benzoxadiazole-4-yl);

N-(5,7-dibromo-2,1,3-benzoxadiazole-4-yl);

N-(6,7-dibromo-2,1,3-benzoxadiazole-4-yl);

N-(5-bromo-6-methyl-2,1,3-benzoxadiazole-4-yl);

N-(5-bromo-7-methyl-2,1,3-benzoxadiazole-4-yl);

N-(6-bromo-7-methyl-2,1,3-benzoxadiazole-4-yl);

N-(5-methyl-6-bromo-2,1,3-benzoxadiazole-4-yl);

N-(5-methyl-7-bromo-2,1,3-benzoxadiazole-4-yl);

N-(6-methyl-7-bromo-2,1,3-benzoxadiazole-4-yl);

N-(5-bromo-6-ethyl-2,1,3-benzoxadiazole-4-yl);

N-(5-bromo-7-ethyl-2,1,3-benzoxadiazole-4-yl);

N-(6-bromo-7-ethyl-2,1,3-benzoxadiazole-4-yl);

N-(5-ethyl-6-bromo-2,1,3-benzoxadiazole-4-yl);

N-(5-ethyl-7-bromo-2,1,3-benzoxadiazole-4-yl);

N-(6-ethyl-7-bromo-2,1,3-benzoxadiazole-4-yl);

N-(5-bromo-6-trifluoromethyl-2,1,3-bendazol-4-yl);

N-(5-trifluoromethyl-6-bromo-2,1,3-benzoxadiazole-4-yl);

N-(5-trifluoromethyl-7-bromo-2,1,3-benzoxadiazole-4-yl);

N-(6-trifluoromethyl-7-bromo-2,1,3-benzoxadiazole-4-yl);

N-(5-chloro-2,1,3-benzoxadiazole-4-yl;

N-(6-chloro-2,1,3-benzoxadiazole-4-yl);

N-(7-chloro-2,1,3-benzoxadiazole-4-yl);

N-(5-nitro-2,1,3-benzoxadiazole-4-yl);

N-(6-nitro-2,1,3-benzoxadiazole-4-yl);

N-(7-nitro-2,1,3-benzoxadiazole-4-yl);

N-(5-bromo-6-tert.-butyl-2,1,3-benzoxadiazole-4-yl);

N-(5-bromo-7-tert.-butyl-2,1,3-benzoxadiazole-4-yl);

N-(6-bromo-7-tert.-butyl-2,1,3-benzoxadiazole-4-yl);

N-(5-tert.-butyl 6-bromo-2,1,3-benzoxadiazole-4-yl);

N-(5-tert.-butyl-7-bromo-2,1,3-benzoxadiazole-4-yl);

N-(6-tert.-butyl-7-bromo-2,1,3-benzoxadiazole-4-yl);

N-(5-chloro-6-methyl-2,1,3-benzoxadiazole-4-yl);

N-(5-chloro-7-methyl-2,1,3-benzoxadiazole-4-yl);

N-(6-chloro-7-methyl-2,1,3-benzoxadiazole-4-yl);

N-(5-methyl-6-chloro-2,1,3-benzoxadiazole-4-yl);

N-(5-methyl-7-chloro-2,1,3-benzoxadiazole-4-yl);

N-(6-methyl-7-chloro-2,1,3-benzoxadiazole-4-yl);

N-(5-dimethylamino-2,1,3-benzoxadiazole-4-yl);

N-(6-dimethylamino-2,1,3-benzoxadiazole-4-yl);

N-(7-dimethylamino-2,1,3-benzoxadiazole-4-yl);

N-(5-cyan-2,1,3-benzoxadiazole-4-yl);

N-(6-cyan-2,1,3-benzoxadiazole-4-yl);

N-(7-cyan-2,1,3-benzoxadiazole- N-(7-methoxycarbonyl-2,1,3-benzoxadiazole-4-yl);

N-(5-etoxycarbonyl-2,1,3-benzoxadiazole-4-yl);

N-(6-etoxycarbonyl-2,1,3-benzoxadiazole-4-yl);

N-(7-etoxycarbonyl-2,1,3-benzoxadiazole-4-yl);

N-(5-acetamido-2,1,3-benzoxadiazole-4-yl);

N-(6-acetamido-2,1,3-benzoxadiazole-4-yl);

N-(7-acetamido-2,1,3-benzoxadiazole-4-yl).

Example 8

A mixture of 4.6 g of 5-dimethylamino-N-(5-bromo-6-ethyl-2,1,3 - benzoxadiazole-4-yl)-1-naphthalenesulfonate and 1.3 g of copper cyanide in 30 ml of pyridine is heated for 8 hours at 120oC. Poured into aqueous ammonia, process as usual and get 5-dimethylamino-N-(5-cyan-6-ethyl-2,1,3-benzoxadiazole-4-yl)-1 - naphthalene-sulfonamide.

Example 9

A solution of 1 g of 5-dimethylamino-N-(5-cyan-6-ethyl-2,1,3 - benzoxadiazole-4-yl)-1-naphthalenesulfonate and 0.7 g of potassium hydroxide in 20 ml of ethanol and 5 ml of water is boiled for 8 hours under stirring. The solvent is removed, the residue is dissolved in water and mixed with hydrochloric acid, and receive a 5-dimethylamino-N-(5 - carboxy-6-ethyl-1,3-benzoxadiazole-4-yl)-1-naphthalenesulfonate.

Example 10

A solution of 1 g of 5-dimethylamino-N-(5-carboxy-6-ethyl-2,1,3 - benzoxadiazole-4-yl)-1-naphthalenesulfonate, 0.5 ml of concentrated sulfuric acid and 30 ml of ethanol is heated for 6 hours at 80oC. Restuccia-4-yl)-1 - naphthalenesulfonate.

Example 11

A solution of 6 g of 4-amino-N-(2,1,3-benzothiadiazole-5-yl)-1-benzene - sulfonamida and 0.5 g of titanium tetrachloride in 10 ml of methanol is mixed with 1 ml of fresh acetaldehyde. Then add 4 g of laborgerate sodium to this solution and stirred for 30 hours. There also add cold policecontributing hydrochloric acid, treated as usual and get 4 ethylamino-N- (2,1,3-benzothiadiazole-5-yl) -1-benzosulfimide.

Example 12

A solution of 1 g of 4-isocyanato-N-(4-bromo-7-methyl-2,1,3 - benzothiadiazole-5-yl)-1-benzosulfimide get by reacting 4-bromo-5-amino-7-methyl-2,1,3-benzothiadiazole with 4 isocyanatobenzene-sulfochloride in 80 ml of toluene is mixed with 0.5 g of pyrrolidine and stirred for 1 hour at 90oC. After conventional treatment receive a 4-pyrrolidino-amido-N-(4-bromo-7 - methyl-2,1,3-benzothiadiazole-5-yl)-1-benzosulfimide.

Example 13

Analogously to example 1, by reacting 5-amino-2,1,3 - benzothiadiazole with the following M-naphthalene-sulfochloride, where M denotes: 5-diethylamino group; 5-isopropylamino group; 5 - isopropyl-methylamino group; 5-methylamino group; 5-ethylamino group; 5-propylamino group; 5-butylamino group; 5-pentylamine group; get SL is propylamino group; 5-isopropyl-methylamino group; 5 - methylamino group; 5-ethylamino group; 5-propylamino group; 5-butylamino group; 5-pentylamine group.

The following examples relate to pharmaceutical compositions.

Example: Glass vials of medicine for injection

A solution of 100 g of biologically active substances of the formula (I) and 5 g of dinitrigenoxide in 3 l of double-distilled water using 2 n hydrochloric acid to establish a pH of 6.5; the solution is sterile filtered, filled them with glass bubbles for drugs for injection, lyophilizer in sterile sterile conditions and closed. Each glass bottle of medicine for injection contains 5 mg of biologically active substances.

Example B: Candles

Melt a mixture of 20 g of biologically active substances of the formula (I) together with 100 g of soya lecithin and 1400 g of cocoa butter, poured into moulds and leave to cool. Each suppository contains 20 mg of biologically active substances.

Example: Solution

Prepare a solution of 1 g of biologically active substances of the formula (I), 9,38 g NaH2PO42H2O, 28,48 Na2HPO412H2O and 0.1 g of benzylaniline in 940 ml of double-distilled water. Set pH 6.8, Dol

Example D: Ointment

Mix 500 mg of biologically active substances of the formula (I) with 99.5 g of vaseline under aseptic conditions.

Example D: Tablets

A mixture of 1 kg of biologically active substances of formula I, 4 kg of lactose, 1.2 kg of potato starch, 0.2 kg of talc and 0.1 kg of magnesium stearate as usual pressed into tablets such that each tablet contains 10 mg of biologically active substances.

Example E: Bean

Analogously to example D is pressed tablets, then the usual way is applied a coating of sucrose, potato starch, talc, tragant and dye.

Example G: Capsules

2 kg of biologically active substances of the formula (I) in the usual way bring into hard gelatin capsules so that each capsule contains 20 mg of biologically active substances.

Example 3: Ampoules

A solution of 1 kg of biologically active substances of formula I in 60 l of double-distilled water is sterile filtered, dispensed into ampoules, lyophilizer in sterile sterile conditions and closed. Each ampoule contains 10 mg of biologically active substances.

Pharmacological data

It was studied the inhibition of some characteristic soedineniya IC50expressed in concentration micromole/liter, corresponding to a 50% increase inhibition of binding of endothelin-1, labeled125I are summarised in the table below.

1. Derivatives of sulfonamides of the formula I

< / BR>
where-A=B-C=D - represents-CH=CH-CH=CH - group in which one CH can be replaced by N;

Ar denotes phenyl or naphthyl, unsubstituted or one-, two - or three-fold substituted with H, Hal, Q, Ph or NR4R5;

R1, R2, R3each independently from each other, is absent or denotes H, Hal or Q;

R4, R5each independently of one another denotes H or Q, Q denotes alkyl with 1 to 6 C-atoms;

Ph denotes phenyl;

X denotes O or S;

Hal denotes F, Cl, Br or I;

n denotes 1, 2 or 3,

and also their salts, except

4-methyl-N-(2,1,3-benzothiadiazole-5-yl)-benzosulfimide,

4-nitro-N-(2,1,3-benzothiadiazole-5-yl)-benzosulfimide,

4-amino-N-(2,1,3-benzothiadiazole-5-yl)-benzosulfimide,

4-methyl-N-(2,1,3-benzothiadiazole-4-yl)-benzosulfimide,

4-nitro-N-(2,1,3-benzothiadiazole-4-yl)-benzosulfimide,

4-amino-N-(2,1,3-benzothiadiazole-4-yl)-benzosulfimide.

2. Derivatives of sulfonamides of formula I on p. 1, p is 3-benzothiadiazole-5-yl)-naphthalenesulfonate,

5-dimethylamino-N-[4-bromo-(2,1,3-benzothiadiazole-5-yl)] -naphthalenesulfonate,

5-dimethylamino-N-(2,1,3-benzothiadiazole-4-yl)-naphthalenesulfonate,

5-dimethylamino-N-(1,2,5-benzoxadiazole-5-yl)-1-naphthalenesulfonate,

5-dimethylamino-N-(6-bromo-7-methyl-1,2,5-benzoxadiazole-5-yl)-1-naphthalenesulfonate,

2-phenyl-N-(2,1,3-benzothiadiazole-5-yl)-benzosulfimide.

3. The method of obtaining compounds of formula I on p. 1, and their salts, which consists in the fact that the compound of formula II

< / BR>
where-A=B-C=D-, R1, R2, R3and X are specified in paragraph 1 values

enter into interaction with the compound of the formula III

Ar-SO2-E,

where E denotes Cl, Br, J, or a free or reactive functionally modified OH - group,

Ar has specified in paragraph (1 value.

4. Pharmaceutical composition having activity against the endothelin receptor, characterized in that it contains one of the compounds of formula I on p. 1 or one of its physiologically acceptable salt in an effective amount.

5. The compounds of formula I under item 1, with activity against the endothelin receptor.

 

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