Method of obtaining a, α,ω-bis-(1, 5, 3-dithiazepinan-3-yl)alkanes

FIELD: chemistry.

SUBSTANCE: invention relates to method of obtaining α,ω-bis-(1,5,3-dithiazepinan-3-yl)-alkanes, which can be applied as antibacterial, antifungal and antiviral agents, as biologically active complexing agents, selective sorbents and extractants of precious metals, special reagents for suppression of vital activity of bacteria in various technical media (from light industry to oil). Essence of method lies in interaction of α,ω-alkanediamine with 1,3,6-oxadithiapinane in presence of catalyst SmCl3·6H2O with mole ratio α,ω-alkanediamine : 1,3,6-oxadithiapinane : SmCl3·6H2O=10:20:(0.3-0.7) at temperature ~20°C and atmospheric pressure for 2.5-3.5 h. Output of α,ω-bis-(1,5,3-dithiazepinan-3-yl)-alkanes (1) constitutes 72-85%.

EFFECT: increase of compound application efficiency.

1 tbl, 1 ex

 

The present invention relates to organic chemistry, specifically to a method for producing α,ω-bis-(1,5,3-diazepine-3-yl)alkanes of the General formula (1):

Nitrogen and sulfur-containing heterocycles are known as antibacterial, antifungal, and antiviral agents (M.R. Stillings, Welbourn A.P., D.J. Walter Substituted 1,3,4-thiadiazoles with anticonvulsant activity // Med. Chem. 1986. 29. P.2280-2284; Kidwai, M., N. Negi, Director S.R. Cyclothiomethylation of arge hydrazines with formaldehyde // Acta Pharma. 1995. 45. P.511; Tyukavkina H.A., Zurabyan SE, Beloborodov V.L. and other Organic chemicals. M.: bustard, 2008. p.66-67). They are promising as catalysts, biologically active agents, selective sorbents and extractants precious metals [Deutsche Gold - und Silber-Scheideanstalt vormals Roessler. F.P. 1,341,792/1963 (Chem. Abs., 1964, 60, 5528d)], special reagents to inhibit bacterial activity in different technical environments (from light industry to oil) (Dzhemilev sea level, Aleev R.S., galinova US, Kunakova W., Khafizova S.R., Kovtunenko S. C., Kalimullin A.A. Andrianov V.M., Ismagilov FR, Gafiatullin P.P. Tool to inhibit the growth of sulfate reducing bacteria. Pat. Of the Russian Federation No. 2160233, 2000; Dzhemilev sea level, Aleev R.S., galinova US, Kunakova W., Khafizova S.R. Means to inhibit the growth of sulfate reducing bacteria. Pat. Of the Russian Federation No. 2206726, 2003).

The known method (Patent RF №2333910; BI, 2008, No. 26) to obtain 5-{2-[5-{2-[1,3,5-d is Tiainen-5-yl]ethyl}-4-methyl-1,3,5-thiadiazine-3-yl]-ethyl}1,3,5-diazinane General formula (2) interaction methyldiethylamine saturated with hydrogen sulfide in an aqueous solution of formaldehyde, taken in a molar ratio methyldiethylamine:formaldehyde:hydrogen of 1:6:4 at a temperature of 20°C with a yield of 63.5%.

The known method cannot be obtained from α,ω-bis-(1,5,3-diazepine-3-yl)alkanes of the General formula (1).

The known method [Fr. Pat. 1,341,792/1963 (Chem. Abs., 1964, 60, 5528d)] obtain derivatives of bis-1,3,5-diazinane, in particular 5-[2-[1,3,5-diazinon-5-yl]ethyl]1,3,5-diazinane (3), the interaction of sodium hydrosulfide with Ethylenediamine and formaldehyde according to the scheme

The known method does not allow to obtain α,ω-bis-(1,5,3-diazepine-3-yl)alkanes of the General formula (1).

The known method (Seraphita, Vremeto, Lphraw, Tavakilov, Grenadilla, Rvenue, Aagrawal, Usmjerili. Multicomponent condensation of aliphatic amines with formaldehyde and hydrogen sulfide. WPI. An. Ser. chem., 2005, 2, 423) obtain 5-[2-[1,3,5-diazinon-5-yl]ethyl]1,3,5-diazinane (3) three-component condensation of hydrogen sulfide with formaldehyde and Ethylenediamine, taken in a molar ratio of 1:6:4 respectively at a temperature of 80°C With a yield of 44%.

The known method does not technological, as it implies the use of gaseous and highly toxic hydrogen sulfide, which at high concentrations, has no smell, but even once its in yanie can cause instant death. In addition, the known method cannot be obtained from α,ω-bis-(1,5,3-diazepine-3-yl)alkanes of the General formula (1).

Thus, the literature contains no information about selective receipt of α,ω-bis-(1,5,3-diazepine-3-yl)alkanes of the General formula (1).

We propose a new method of obtaining α,ω-bis-(1,5,3-diazepine-3-yl)alkanes of the General formula (1).

The method consists in the interaction of α,ω-alkadiene General formula H2N-CH2-(CH2)n-NH2where n=1-8, 1,3,6-oxidationand in the presence of a catalyst SmCl3·6N2Oh, taken in a molar ratio of α,ω-alindeman:1,3,6-oxidational:SmCl3·6N2O=10:20:(0.3-0.7), preferably 10:20:0.5. The mixture is stirred for 2.5-3.5 hours at a temperature of 20°C and atmospheric pressure in chloroform (l3) as solvent. The output of the α,ω-bis-(1,5,3-diazepine-3-yl)alkanes (1) is 72-85%. The reaction proceeds according to the scheme

α,ω-Bis-(1,5,3-diazepine-3-yl)alkanes of the General formula (1) are formed only with the participation of 1,3,6-oxidationin and α,ω-alkadienes taken in a molar ratio of 20:10 (stoichiometric amount). When a different ratio of initial reagents reduces the yield of the target product (1). In the presence of other aldehydes (e.g., alkyl substituted aldehydes), other developed (for example, 1,4-butanediol, 1,2-vinelandii is) or other diamines (for example, 1,2 - or 1,4 - phenylendiamine) target products (1) are not formed. Without catalyst, the reaction proceeds with output not exceeding 30%.

The conduct of a specified reaction in the presence of a catalyst SmCl3·6H2O more than 7 mol.% does not lead to a significant increase in the yield of the target product (1). The use of catalyst SmCl3·6H2O less than 3 mol.% reduces output (1), which is connected, possibly, with a reduction of catalytically active sites in the reaction mass. The reaction was carried out at a temperature of 20°C. At temperatures above 20°C (e.g., 60°C) increase energy costs, and at temperatures below 20°C (for example, at 0°C) decreases the reaction rate. The experiments were carried out in chloroform, as well dissolve the target products.

Significant differences of the proposed method

In the known method the reaction proceeds with participation as a source of reactant gaseous hydrogen sulfide at a temperature of 80°C with the formation of six-membered N,S-containing heterocycles, namely 5-[2-[1,3,5-diazinon-5-yl]ethyl]1,3,5-diazinane (3). The known method does not allow the individual α,ω-bis-(1,5,3-diazepine-3-yl)alkanes (1) the General formula (1).

In the proposed method, the reaction proceeds with participation as a source of reagent 1,3,6-oxidationin at a temperature of 20°C under the action of catalyst SmCl3·6H2O. In contrast to the known h is aemy method allows you to obtain an individual α,ω-bis-(1,5,3-diazepine-3-yl)alkanes of the General formula (1), the synthesis of which are not described in literature.

The method is illustrated by examples.

Example 1. In the vessel Slanka mounted on a magnetic stirrer, an argon atmosphere at a temperature of ~20°C is placed 10 mmol of academia and 0.5 mmol Sml3·6N2O, then add 20 mmol 1,3,6-oxidationin in 10 ml of chloroform. The reaction mixture is stirred at a temperature of ~20°C for 3h, add 2 ml of H2O and extracted with chloroform.

Chloroform fraction purified column chromatography on SiO2allocate α,ω-bis-(1,5,3-diazepine-3-yl)ethane with the release of 79%.

Other examples of the method are given in table 1.

Table 1
№№ p/pSource α,ω-diamineThe ratio of α,ω-diamine:1,3,6-oxidational:SmCl3·6N2O mmolReaction time, hours.Output(1), %
11,2-amandemen10:20:0.5379
2-"-10:20:0.3372
3-"-10:20:0.7385
4-"-10:20:0.52.574
5-"-10:20:0.53.583
61,3-amandemen10:20:0.5380
71,4-amandemen10:20:0.5381
81,5-amandemen10:20:0.5378
91,6-amandemen10:20:0.5384
101,7-amandemen10:20:0.5377
111,8-echandia the Ying 10:20:0.5375
121,9-amandemen10:20:0.5382

All experiments were performed in chloroform at room temperature (~20°C).

The spectral characteristics of the α,ω-bis-(1,5,3-diazepine-3-yl)ethane (Control reaction was carried out by TLC on Silufol plates W-254, showed pairs I2. For column chromatography was used silica gel KSK (100-200 μm). The melting point is defined on the device OOC 80/2617. The NMR spectra of 1D (1H,13C) and 2D (COSY, NOESY, HSQC, NMVS) removed spectrometer Bruker Avance 400 (100.62 MHz for13And 400.13 MHz for1H) by standard methods (Bruker, internal standard Me4Si, solvent - Dl3. Mass high resolution spectra obtained on the instrument MALDI TOF/TOF AUTOFLEX III (Bruker).):

TPL 144-145°C. Eluent hexane: ethyl acetate (4:3), Rf0.5. An NMR spectrum1H, δ, ppm: 2.86 (USS, 4H, CH2(8, 9)); 3.06 (USS, 8H, CH2(6,6',7,7')); 4.20 (USS, 8H, CH2(2,2',4,4')). An NMR spectrum13S, δ, ppm: 35.81 (t, C-6, C-6', C-7, C-7'), 47.77 (t, C-8, C-9), 59.71 (t, C-2, C-2', C-4, C-4'). MALDI TOF, m/z: 297.333 [M+H]+. C10H20N2S4. M 296.543.

The spectral characteristics of the α,ω-bis-1,5,3-diazepine-3-yl)-propane:

TPL 73-74°C. Eluent hexane:ethyl acetate (4:3), Rf0.5. An NMR spectrum 'N, δ, ppm: 1.77 (m, 2H, CH2(9)); 2.74 (m, 4H, CH2(8, 10)); 3.04 (USS, 8H, CH2(6, 6', 7, 7')); 4.15 (USS, 8H, CH2(2,2',4,4')). An NMR spectrum13S, δ, ppm: at 24.48 (t, C-9), 35.88 (t, C-6, C-6', C-7, C-7'), 48.67 (t, C-8, C-10), 59.54 (t, C-2, C-2', C-4, C-4').

The spectral characteristics of the α,ω-bis-(1,5,3-diazepine-3-yl)-butane:

TPL 122-123°C. Eluent hexane:ethyl acetate (4:3), Rf0.5. An NMR spectrum1N, δ, ppm: 1.48 (USS, 4H, CH2(9, 10)); 2.68 (USS, 4H, CH2(8,11)); 3.03 (USS, 8H, CH2(6,6',7,7')); 4.15 (USS, 8H, CH2(2,2',4,4')). An NMR spectrum13S, δ, ppm: 24.68 (t, C-9, C-10), 35.90 (t, C-6, C-6', C-7, C-7'), 50.64 (t, C-8, C-11), 59.51 (t, C-2, C-2', C-4, C-4'). MALDI TOF, m/z: 347.287 [M+Na]+C12H24N2S4. M 324.596.

The spectral characteristics of the α,ω-bis-(1,5,3-diazepine-3-yl)-pentane:

Eluent hexane:ethyl acetate (4:3), Rf0.5. An NMR spectrum1H, δ, ppm: 1.35 (m, 2H, CH2(10)); 1.48 (m, 4H, CH2(9, 11)); 2.67 (t, J=7.2 Hz, 4H, CH2(8, 12)); 3.04 (USS, 8H, CH2(6, 6', 7, 7')); 4.16 (USS, 8H, CH2(2, 2', 4, 4')). An NMR spectrum13S, δ, ppm: 25.01 (t, C-10), 26.78 (t, C-9, C-11), 35.94 (t, C-6, C-6', C-7, C-7'), 50.86 (t, C-8, C-12), 59.51 (t, C-2, C-2', C-4, C-4').

The spectral characteristics of the α,ω-bis-(1,5,3-diazepine-3-yl)-hexane:

TPL 84-86°C. Eluent hexane:ethyl acetate (4:3), Rf0.5. An NMR spectrum1H, δ, ppm: 1.35 (USS, 4H, CH2(10, 11)); 1.46 (USS, 4H, CH2(9, 12)); 2.67 (m, 4H, CH2(8, 13)); 3.05 (d, J=10.4 Hz, 8H, CH2(6,6',7,7')); 4.17 (d, J=10.4 Hz, 8H, CH2(2,2',4,4')). An NMR spectrum13S, δ, ppm: 26.96 (t, C-10, C-11); 27.16 (t, C-9, C-12); 35.93 (t, C-6, C-6', C-7, C-7'), 50.91 (t, C-8, C-13), 59.56 (t, C-2, C-2', C-4, C-4'). MALDI TOF, m/z: 375.241 [M+Na]+. C14H28N2S4. M 352.649.

The spectral characteristics of the α,ω-bis-(1,5,3-diazepine-3-yl)-heptane:

TPL 69-70°Salient hexane:ethyl acetate (4:3), Rf0.45. An NMR spectrum1N, δ, ppm: 1.33 (USS, 8H, CH2(9, 10, 12, 13)); 1.45 (USS, 2H, CH2(11)); 2.66 (t, J=8.8 Hz, 4H, CH2(8, 14)); 3.05 (USS, 8H, CH2(6,6',7,7')); 4.17 (USS, 8H, CH2(2,2',4,4')). An NMR spectrum13S, δ, ppm: 26.97 (t, C-10, C-12), 27.27 (t, C-9, C-13), 29.30 (t, C-11), 35.94 (t, C-6, C-6', C-7, C-7'), 50.98 (t, C-8, C-14), 59.56 (t, C-2, C-2', C-4, C-4'). MALDI TOF, m/z: 389.271 [M+Na]+. C15H30N2S4. M 366.676.

The spectral characteristics of the α,ω-bis-(1,5,3-diazepine-3-yl)-octane:

TPL 70-71°C. Eluent hexane:ethyl acetate (4:3), Rf0.45. An NMR spectrum1N, δ, ppm: 1.32 (USS, 8H, CH2(10, 11, 12, 13)); 1.58 (USS, 4H, CH2(9,14)); 2.67 (t, J=7.2 Hz, 4H, CH2(8, 15)); 3.06 (USS, 8H, CH2(6,6',7,7')); 4.18 (USS, 8H, CH2(2,2',4,4')). An NMR spectrum13S, δ, ppm: 27.01 (t, C-10, C-13), 27.27 (t, C-9, C-14), 29.40 (t, C-11, C-12), 35.95 (t, C-6, C-6', C-7, C-7'), at 51.03 (t, C-8, C-15), 59.58 (t, C-2, C-', C-4, C-4'). MALDI TOF, m/z: 381.319 [M+H]+. With16H32N2S4. M 380.702.

The spectral characteristics of the α,ω-bis-(1,5,3-diazepine-3-yl)-nonane:

TPL 60-62°C. Eluent hexane: ethyl acetate (4:3), Rf0.45. An NMR spectrum1H, δ, ppm: 1.31 (USS, 8H, CH2(9, 10, 14, 15)); 1.44 (m, 4H, CH2(11, 13)); 1.58 (USS, 2H, CH2(12)); 2.67 (t, J=7.2 Hz, 4H, CH2(8, 16)); 3.06 (USS, 8H, CH2(6,6',7,7')); 4.18 (USS, 8H, CH2(2, 2', 4, 4')). An NMR spectrum13S, δ, ppm: 27.03 (t, C-10, C-14), 27.31 (t, C-9, C-15), 29.41 (t, C-11, C-13), 29.51 (t, C-12), 35.95 (t, C-6, C-6', C-7, C-7'), 51.05 (t, C-8, C-16), 59.58 (t, C-2, C-2', C-4, C-4'). MALDI TOF, m/z: 417.258 [M+Na]+. C17H34N2S4. M 394.729.

The method of obtaining α,ω-bis-(1,5,3-diazepine-3-yl)alkanes of the General formula (1):

characterized in that the α,ω-alkadiene General formula H2N-CH2-(CH2)n-NH2where n=1-8, is subjected to the interaction with 1,3,6-oxidationand in chloroform in the presence of a catalyst SmCl3·6N2O when the molar ratio of α,ω-alindeman:1,3,6-oxidational:SmCl3·6N2O=10:20:(0,3-0,7) under room temperature (~20°C) temperature for 2.5 to 3.5 hours



 

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FIELD: chemistry.

SUBSTANCE: invention relates to a compound of formula or a pharmaceutically acceptable salt thereof, in which R1 denotes hydrogen or C1-6alkyl; R2 denotes isooxazolyl group, substituted with C1-6alkyl; RB denotes -CF3, -CHF2, -CH2F, or C1-6alkyl. The invention also relates to pharmaceutical compositions for treating cancer which contain the disclosed compounds.

EFFECT: obtaining novel compounds and a pharmaceutical compositions based on said compounds, which can be used in medicine for treating cancerous diseases.

15 cl, 77 dwg, 10 tbl, 13 ex

FIELD: medicine, pharmaceutics.

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16 cl, 2 tbl, 307 ex

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of general formula (I),

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7 cl, 4 ex, 1 tbl

FIELD: chemistry.

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EFFECT: method of obtaining novel compounds which can be used as selective sorbents and extraction agents of precious metals, agents for protecting leather, fur and textile from biodeterioration, biologically active substances with respect to different microorganisms and sulphate-reducing bacteria.

1 cl, 1 tbl, 1 ex

FIELD: chemistry.

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EFFECT: method of obtaining novel compounds which can be used as selective sorbents and extraction agents of precious metals, agents for protecting leather, fur and textile from biodeterioration, biologically active substances with respect to different microorganisms and sulphate-reducing bacteria.

1 cl, 1 tbl, 1 ex

FIELD: chemistry.

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FIELD: chemistry.

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32 cl, 23 dwg, 184 tbl, 1535 ex

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of general structural formula:

or to pharmaceutically acceptable salts, where Z denotes -O- or -CH2- or -CH2-CH2-; X1 denotes a covalent bond or -O-; Y1 denotes a covalent bond or C1-C10 alkylene, provided that Y1 is a covalent bond only when X1 denotes a covalent bond; R1 denotes a) (C3-C7)cycloalkyl or b) phenyl or heteroaryl, which is a monovalent heteroatomatic monocyclic radical ring containing 1-2 heteroatoms, independently selected from nitrogen and sulphur, possibly substituted with 1-3 groups, independently selected from fluorine, chlorine, bromine, (C1-C6)alkyl or (C1-C6)-alkoxy; R2 denotes -OC(O)(NH2), -OC(O)(NHR9), -NHC(O)OR9, -C(O)R9, -C(O)(NH2), -C(O)(NHR9) or -NHC(O)H, where R9 denotes a linear or branched C1-C5 alkyl or a linear or branched (C1-C5)alkoxyalkyl; R3 denotes H, C1-C5 alkyl, -NHC(O)R10 or OH, where R10 denotes C1-C3 alkyl, provided that when R3 denotes -OH, X1 is not O and R2-Y1-X1 is not -OC(O)(NH2), -OC(O)(NHR9), -NHC(O)OR9 or -NHC(O)H; -Q denotes

, where N and N are bonded by bonds denoted by a wavy line; R4 denotes H; R5 and R6 independently denote: a) H, (C1-C10)alkyl, (C4-C10)cycloalkylalkyl, hydroxylated (C4-C10)cycloalkylalkyl, halo(C4-C10)cycloalkylalkyl, (C1-C2)alkyl(C4-C10)cycloakylalkyl, (C4-C10)bicycloalkyl(C1-C3)alkyl, (C1-C5)alkoxy(C1-C5)alkyl; or a saturated heterocyclyl(C1-C3)alkyl, where the saturated heterocyclic ring is selected from 5-, 6- or 7-member heterocyclic rings which contain 1 heteroatom independently selected from N and O; or b) phenyl(C1-C2)alkyl, phenoxymethyl, each of which is possibly with 1-3 groups independently selected from fluorine, chlorine, (C1-C3)alkyl, (C1-C3)alkoxy; provided that both R5 and R6 are not H; G denotes NH2 or NHR7; R7 denotes (C1-C6)alkyl; or R5 and R7 together denote -CH2, -(CH2)2 or -(CH2)3, possibly substituted with 1-2 groups independently selected from (C1-C8)-alkyl, (C3-C6)cycloalkyl, (C3-C6)cycloalkyl(C1-C2)alkyl or (C1-C8)alkoxy. The invention also relates to compounds selected from the group, pharmaceutical compositions, a method for antagonising one or more aspartate proteases, as well as methods of treating aspartate protease-mediated disorders.

EFFECT: obtaining novel biologically active compounds having activity towards rennin.

35 cl, 33 ex, 4 dwg

FIELD: chemistry.

SUBSTANCE: invention relates to method of obtaining 3-(o-,m-,p-methoxyphenyl)-1,5,3-dithiazepanes, which can be applied as antibacterial, antifungal and antiviral agents, as biologically active complexing agents, selective sorbents and extractants of precious metals, special reagents for suppression of vital activity of bacteria in various technical media. Essence of method lies in preliminary mixing of formaldehyde with 1,2-ethanedithiole with further addition of o-,m-,p- methoxyaniline and mixing at temperature ~20°C and atmospheric pressure for 20-40 minutes. Output of 3-(o-, m-, n-methoxyphenyl)-1,5,3-dithiazepanes (1) constitutes 59-87%.

EFFECT: increase of compound application efficiency.

1 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: method of obtaining 3-aryl-1,5,3-dithiazepanes of general formula , where R=H, m-Me, n-MeO, m-NO2, lies in the following: 3-tret-butyl-1,5,3-dithiazepane is subjected to interaction with N-arylamines (aniline, m-methylaniline, n-methoxyaniline, m-nitroaniline) in presence of catalyst Sm(NO3)3·6H2O in mole ratio 3-tret-butyl-1,5,3-dithiazepane : N-arylamine : Sm(NO3)3·6H2O=10:(10-12):(0.3-0.7) in chlorophorm and argon atmosphere for 2.5-3.5 h.

EFFECT: elaborated is method of obtaining with high selectivity of novel 3-aryl-1,5,3-dithiazepanes, which can be applied as antibacterial, antifungal and antiviral agents, as complexing agents, selective sorbents and extractants of precious metals, special reagents for suppression of vital activity of bacteria in various technical media.

1 cl, 1 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: method of obtaining N-aryl-1,5,3-dithiazepanes of general formula (I): , where Ar = Ph, m-Me-C6H4, o-MeO~C6H4, n-NO2-C6H4, lies in the following: 1,3,6-oxadithiepane is subjected to interaction with N-arylamines (aniline, m-methylaniline, o-methoxyaniline, n-nitroaniline) in presence of catalyst Sm(NO3)3·6H2O in mole ratio 1,3,6-oxadithiepane : N-arylamine : Sm(NO)3)3·6H2O = 10:(10-12):(0.3-0.7) in chlorophorm and argon atmosphere for 2.5-3.5 h.

EFFECT: elaborated is method of obtaining with high selectivity of novel N-aryl-1,5,3-dithiazepanes, which can be applied as antibacterial, antifungal and antiviral agents, as complexing agents, selective sorbents and extractants of precious metals, special reagents for suppression of vital activity of bacteria in various technical media.

1 cl, 1 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to method of obtaining 2- and 4-(1,5,3-dithiazepinsan-3-yl) phenols, which can be applied as antibacterial, antifungal and antiviral agents, as biologically active complexing agents, selective sorbents and extractants of precious metals, special agents for suppression of vital activity of bacteria in various technical media. Essence of method lies in preliminary mixing of formaldehyde with 1,2-ethanedithiole with further addition of o-, n-aminophenol and mixing at temperature ~20°C and atmospheric pressure for 2-4 hours. Output of 2- and 4-(1,5,3-dithiazepinsan-3-yl) phenols (1) constitutes 60-75%.

EFFECT: method improvement.

1 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing N-phenyl(benzyl)-1,5,3-dithiazepinane-3-amines and 2,4-dimethyl-N-phenyl(benzyl)-1,5,3-dithiazepinane-3-amines of general formula (1): R=Ph, Bz; R'=H, Me, which involves first mixing formaldehyde or acetaldehyde with 1,2-ethanedithiol and then adding phenylhydrazine (benzylhydrazine) in molar ratio of initial reactants aldehyde: 1,2-ethanedithiol: phenylhydrazine (benzylhydrazine)=20:10:10 and stirring at temperature 0°C and atmospheric pressure for 2-4 hours.

EFFECT: method of obtaining novel compounds which can be used as antibacterial, antifungual and antiviral agents, as biologically active complexing agents, selective sorbents and extractants of precious metals, special reagents for inhibiting bacterial activity in different process media.

1 cl, 1 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to derivatives of 1,3,4-thiadiazolines (I), thiadiazinones (II) and thiadiazepines (III), obtained based on thiohydrazides of oxamic acids, which can be used to inhibit pathogenic bacteria, and can particularly affect type III secretion system in pathogens, having general formula:

, , ,

where R denotes H; R1 denotes H, pyridinyl; phenyl, substituted with alkyl C1-C5, Hal, CF3; a group , where X denotes S, substituted with alkyl C1-C5, COOR4; R2, R3 denotes alkyl C1-C5, pyridinyl, phenyl, substituted Hal, OH, OR4, a R4 denotes unsubstituted alkyl C1-C4.

EFFECT: obtaining compounds which can be used to inhibit pathogenic bacteria.

2 cl, 2 dwg, 6 tbl, 21 ex

FIELD: chemistry.

SUBSTANCE: N,S-containing heterocycle obtained using the disclosed method can be used as a selective sorbent and extraction agent for precious metals, and as a special reagent for inhibiting bacterial action in different media. The method involves reaction of hydrogen sulphide-saturated aqueous formaldehyde solution with o-aminothiophenol in the presence of EtOH at 20-80°C and stirring for 3 hours. Output of the desired product is equal to 79% at 20°C and 83% at 80°C.

EFFECT: high output.

1 cl, 1 ex

FIELD: organic chemistry, medicine.

SUBSTANCE: invention relates to benzothiadiazepine derivatives of general formula I wherein M represents -N-one of R4 and R5 representsgroum of formula ring A represents aryl; or hydrolysable in vivo pharmaceutically acceptable salts, esters and amides thereof. Such derivatives are useful as inhibitors of bile acid transfer in ileal intestine (IBAT) for hyperlipemia treatment. Methods for production of abovementioned derivatives also are described.

EFFECT: new benzothiadiazepine derivatives for hyperlipemia treatment.

14 cl, 67 ex

FIELD: organic chemistry, organic synthesis, chemical technology.

SUBSTANCE: invention relates to a method for combined synthesis of 3,4-diphenyl-1,3,4-thiadiazolidine of the formula (1a): and 5,6-diphenyltetrahydro-1,3,5,6-dithiadiazepine of the formula (1b): Method involves interaction of formaldehyde aqueous solution saturated with hydrogen sulfide with 1,2-diphenylhydrazine in a buffer solution butanol-sodium butylate: n.-BuOH/n.-BuONa taken in the mole ratio 1,2-diphenylhydrazine : formaldehyde : hydrogen sulfide : sodium butylate = 1:2:1:2, respectively, at temperature 20-40°C and at stirring 3 h. The yield of the end substance of the formula (1a) is 39% and that of the formula (1b) is 22%. Synthesized substances can be used as selective sorbents and extractants of previous metals, special reagents for inhibition of vital activity of microorganisms in different media, biologically active substances used in synthesis of different medicinal preparations, for example, anti-bacterial, anti-fungal and anti-viral agents.

EFFECT: improved method of synthesis.

FIELD: organic chemistry, organic synthesis, chemical technology.

SUBSTANCE: invention relates to a method for combined synthesis of 3,4-diphenyl-1,3,4-thiadiazolidine of the formula (1a): and 5,6-diphenyltetrahydro-1,3,5,6-dithiadiazepine of the formula (1b): Method involves interaction of formaldehyde aqueous solution saturated with hydrogen sulfide with 1,2-diphenylhydrazine in a buffer solution butanol-sodium butylate: n.-BuOH/n.-BuONa taken in the mole ratio 1,2-diphenylhydrazine : formaldehyde : hydrogen sulfide : sodium butylate = 1:2:1:2, respectively, at temperature 20-40°C and at stirring 3 h. The yield of the end substance of the formula (1a) is 39% and that of the formula (1b) is 22%. Synthesized substances can be used as selective sorbents and extractants of previous metals, special reagents for inhibition of vital activity of microorganisms in different media, biologically active substances used in synthesis of different medicinal preparations, for example, anti-bacterial, anti-fungal and anti-viral agents.

EFFECT: improved method of synthesis.

FIELD: organic chemistry, medicine.

SUBSTANCE: invention relates to benzothiadiazepine derivatives of general formula I wherein M represents -N-one of R4 and R5 representsgroum of formula ring A represents aryl; or hydrolysable in vivo pharmaceutically acceptable salts, esters and amides thereof. Such derivatives are useful as inhibitors of bile acid transfer in ileal intestine (IBAT) for hyperlipemia treatment. Methods for production of abovementioned derivatives also are described.

EFFECT: new benzothiadiazepine derivatives for hyperlipemia treatment.

14 cl, 67 ex

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