Furazan derivatives, synthesis method thereof and energy compositions containing said compounds

FIELD: chemistry.

SUBSTANCE: invention relates to a compound of formula (I):

, where: R=NO2, or and Het denotes an azolyl radical selected from nitroazolyl and tetrazolyl radicals; except 3- and nitro-4-(4-nitro-1,2,3-triazol-1-yl)furazan. The invention also describes a method of producing a compound of formula I and an energy composition based on said compounds.

EFFECT: compounds have high energy characteristics, low sensitivity and high thermal stability.

11 cl, 7 ex, 3 tbl, 2 dwg

 

The technical FIELD

The present invention relates to:

- new heterocyclic molecules: new compounds derived from furazane in the reaction of interaction of furazan and Isola;

- preparation of new molecules; and

- new energetic compositions.

New connections (new molecules) are extremely useful because they are both energy and are characterized by reduced vulnerability because especially preferably they have the following characteristics:

- high energy specifications,

- low sensitivity and

- high thermal stability.

Furutani refer to nitrogen-containing heterocyclic compounds, characterized by high formation enthalpies due to the energy reference to ha (busy) rings. The energy of such compounds is a potential that along with their high thermal stability ensures their preferred promising application in the field of energetic materials.

PRIOR art

In 1991, in the first patent document US 5071495 described the use of furazane type diaminofurazan (DAF) in alliterating components propellant containing ammonium perchlorate. Such furutani used at very low conc is ntrace, and consider the components of rocket fuel showed relatively low specifications.

Later in patent document EN 2248354 describes the synthesis of furazan with high molecular weight (molar mass = 420 g/mol), which is thermally stable (decomposition temperature of 267°C) and which can be used in the composition of explosives that can be operated at relatively high temperatures inside boreholes. Technical characteristics specified in the document, are also low (velocity of detonation: 8090 km/s).

In the patent document FR 2750421 Chassaing and Finck describe the application of charges containing dinitrobiphenyl, and demonstrate high energy potentials. However, these compounds have certain disadvantages, in particular, chemical instability and incompatibility with binders and additives that are present in components of rocket fuel and explosives. Sheremetiev and other Heteroatom. Chemistry, 2000, 11, 48, showed that dinitrobenzofuroxan can be split by toxicwaste or at the carbon atom that bears one or two nitro, in the presence of nucleophiles, such as alcohols. Such reactions easily occur when the ambient temperature.

In the publication, International Annual Conference of ICT (1999), 30th, 57/1-57/11) described 4-n the tro-3-(4,5-dinitro-1H-1,2,3-triazole-1-yl)-1,2,5-oxadiazol. However, the publication does not contain descriptions of receipt of this connection. The publication includes the calculation of the expected characteristics, based on the hypothetical chemical structure of the compounds.

In another publication (proceedings of the Academy of Sciences, Chemical series, T, No.6, str-1418 (June, 2003)) describes the synthesis of (pyrrol-1-yl)forzano. Parastasie heterocycles mentioned furazane are unsubstituted.

In two publications in the proceedings of the Academy of Sciences, Chemical series, T, No.8, str-1922 and str-1934 (August 2005)) describes the synthesis of derivatives of (1,2,3-triazole-1-yl)-1,2,5-oxadiazole. 3-Nitro-4-(4-nitro-1,2,3-triazole-1-yl)furazan described in publications as an individual connection.

Specialist in the art is always interested in new energy connections with preferred characteristics, vulnerability and thermal stability. Currently, there are no documents that contain information about the efficient use of furazane in the field relating to components of rocket fuel and explosives. In addition, the specialist in the art often ignores furutani because of their high vulnerability to dynamic load and friction.

The INVENTION

The authors of the present invention unexpectedly discovered a new class of furazane, is the quiet are extremely effective with regard to specifications, above.

New furutani represent the first object of the present invention. They have the formula (I)below:

where

R=-NO2,,

or;

and Het represents solely radical selected from nitroanaline and tetrazolyl radicals;

and new furutani are not 3-nitro-4-(4-nitro-1,2,3-triazole-1-yl)farzana (see above).

New furutani are monourethane (R=-NO2or beforesave (R = other 4 radical, as defined above).

Het represents solely radical, i.e. received a 5-membered nitrogen-containing heterocycle, at least one of the nitrogen atoms associated with hydrogen atom. Het represents solely radical selected from nitroaniline radicals (asailing radicals, substituted by at least one nitro-group) and tetrazolyl radical (unsubstituted tetrazolyl radicals).

Het typically includes a single heterocycles (5-membered) heterocycle or two (5-membered), connected through a communication C-C.

Preferably Het is chosen from:

- unsubstituted tetrazolyl and literatlly ((bi)tetrazolyl) radicals;

- pyrrolidine and bipyrrole ((bi)pyrrolidine) for the Alov, substituted by at least one nitro-group;

- pyrazolidine and seperatelly ((bi)parasailing) radicals, substituted by at least one nitro-group;

- triazolyl and Petriashvili ((bi)triazolyl) radicals, substituted by at least one nitro-group (particularly preferably, these radicals and especially triazole radicals substituted by only one nitro-group); and

- tetrazolyl and literatlly ((bi)tetrazolyl) radicals, substituted by at least one nitro-group.

Het, in particular, may be selected from nitrotriazole (in particular, nitro-1,2,3-triazolines and nitro-1,2,4-triazoline); dinitrocresols; dinitropyridine (3,4-dinitropyridine and 3.5-dinitropyridine); tetrazolyl; 5-nitrotetrazolato; poly(nitropyrrole) (particularly preferably bi(nitropyrrole)); literatlly; bi(nitrotriazole) and bi(dinitropropyl) radicals.

Preferably Het is chosen from the following radicals:

3-nitro-1,2,4-triazole-1-yl,

4-nitro-1,2,3-triazole-2-yl,

4-nitro-1,2,3-triazole-1-yl,

3,4-dinitrobenzoyl,

3,5-dinitrobenzoyl,

1,2,3,4-tetrazol-1-yl.

In the context of the first aspect of the present invention, the present invention includes new compounds of formula (I)defined below:

- 3-nitro-4-(3-nitro-1,2,-triazole-1-yl)furazan,

- 3-nitro-4-(4-nitro-1,2,3-triazole-2-yl)furazan,

- 4-nitro-4'-(4-nitro-1,2,3-triazole-2-yl)misfortunately ether,

- 4-nitro-4'-(4-nitro-1,2,3-triazole-1-yl)-3,3'-ethoxysulfuron,

- 3-nitro-4-(3,4-dinitrobenzoyl)furazan,

- 3-nitro-4-(3,5-dinitrobenzoyl)furazan.

According to the second aspect of the present invention, the present invention relates to the production of new compounds of the formula (I).

For the most part, the new compounds can be obtained in a completely new way through a reaction between nitrofurazone formula (IIa)

where R is as defined above in the description of the compounds of formula (I), and

Azola formula (IIb):

where Het is as defined above in the description of the compounds of formula (I).

The reaction of interaction leads to nucleophilic substitution mono - or beforesave (formula (IIa)containing leaving the nitrogroup) azole of the formula (IIb).

The reaction is carried out in the presence of an organic or inorganic base in a polar organic solvent, preferably an anhydrous polar organic solvent. In particular, the used solvent may be selected from acetone, tetrahydrofuran, dimethylformamide, dimethyl sulfoxide, acetonitrile, nitromethane, sulfolane and mixtures thereof. The reaction can is t be carried out at a temperature, in the range between ambient temperature and the boiling point of the used solvent. Preferably the reaction of the interaction is carried out in acetonitrile at ambient temperature.

When nucleophilic substitution therefore, nitrofurazan formula (IIa) acting as the electrophile, choose from:

a) dinitropropane,

b) dinitropropanol ether,

c) dinitrosobenzene,

d) dinitrosobenzene, and

e) denitrogenation.

These compounds (monoporosa for compound (a), beforeany for compounds (b)to(e) described in the literature. In particular, compounds (a)-(d) are disclosed in:

- Aberotel and other Mendeleev Commun. 1994, 138-140; or

- Aberotel and other Mendeleev Commun. 1998, 238.

The compound (e) are disclosed in particular in patent document US 6,388,087.

Many azoles of the formula (IIb) can act as nucleophiles. In particular, they include azoles, corresponding hasolelim radicals described above. These azoles are essentially known connections.

The reaction of the interactions defined above, suitable for all compounds in accordance with the present invention. As illustrated in Examples 1, 2, 6 and 7 below.

However, some of the compounds according to the present invention can be perceived by the s under more favorable conditions using other methods. Below the present invention provides such "other", more selective methods.

Preferably, in order to obtain higher selectivity) subclass of compounds of formula I where Het represents:

- 1,2,3,4-tetrazol-1-ilen radical; or

- 5-nitro-1,2,3-triazole-2-ilen radical; or

- 4-nitro-1,2,3-triazole-1-ilen radical

in accordance with other ways in which the source material is aminopyrazine formula (IIIa):

where R is as defined above.

To obtain the compounds of formula (I), where Het is tetrazolyl radical, as defined above, is recommended:

- add orthoformiate of the functional amino group aminopyrazine formula (IIIa) (by sequential reaction with, for example, metalitalia.com and sodium azide).

Path A, the chemical reaction shown above is summarised in the diagram below.

To obtain the compounds of formula (I), where Het is diazolidinyl radical, as defined above, is recommended:

the diazotization aminopyrazine formula (IIIa) with NaNO2in a concentrated acid medium followed:

- to obtain 4-(5-nitro-1,2,3-triazole-2-yl)furazan (below):

the condensation of the resulting diazonium with whom and with nitroacetanilide;

- dehydration of the resulting product in the presence of inorganic or organic anhydride, in particular, in the presence of acetic anhydride (cyclization);

to obtain 4-(4-nitro-1,2,3-triazole-1-yl)furazan (C below):

the interaction of the obtained diazonium salt with sodium azide to obtain azidopyridine formula

where R is as defined above;

- cyclopentadiene azidopyridine and morpholinosydnonimine.

Two series of chemical reactions described above (including the path B or C), represented in the General form in the diagram below.

Nitrosomethyl considered heterocycle (Het = diazolidinyl radical) has no effect on the exercise of the reactions.

Both paths (paths B and C) include the same intermediate compound (diazonium salt source aminopyrazine). Depending on the chosen path (B or C), the relationship with the ring of furazan can be:

or through the Central nitrogen atom (2) (),

or through a nitrogen atom (1) ring 4-nitro-1,2,3-triazole (path).

The conditions described Licht and Ritter (J. Energ. Mat, 1994, 12, 223-35), using nitroacetanilide lead to the formation of the connection furazan-heterocycle through the Central nitrogen atom (2) ring 4-nitro-1,2,3-triazole. The second path, which includes Simocatta intermediate azidopyridine and morpholinosydnonimine (Batog et al., Chemistry of Heterocyclic Compounds, 2000, 36, 343), leads to the formation of the connection furazan-heterocycle via a nitrogen atom (1) ring 4-nitro-1,2,3-triazole.

The practical implementation of path B, above, is illustrated in Example 3 below.

As for C, it is obvious that it may be a limited cyclopentadiene azidopyridine and morpholinosydnonimine, provided that azidopyridine is available. Actually azidopyridine may be a known compound (where R represents nitro, nitrosoguanidine or nitrosodimethylaniline radical). The specified stage of condensation is illustrated in Example 5 below.

According to the present invention also provides a more efficient method of obtaining the compounds of formula (I), where

and Het = 1,2,3,4-tetrazol-1-ilen radical, 4-(4-nitro-1,2,3-triazole-1-yl) radical or 4-(5-nitro-1,2,3-triazole-2-yl) radical.

This method involves the reactions listed above, the path A, the diazotization + path B or the diazotization + C, using as the starting material hydroxyfuran formula (IVa):

in order to get hydroxyfuran, functionalized with azole, followed by interaction of the primary environment functionalized hydroxyphenazine with dinitropropane is a new prosthemadera.

In those cases, when functionalized hydroxyfuran get through In specified a way that can be represented in General form as follows:

Thus "directly" get asymmetric ethers. Consider the reaction of transesterification is described, for example, Sheremetyeva A.B. - proceedings of the Academy of Sciences, Chemical series, 2000, 51, 659. It is in the interaction dinitropropanol ether with hydroxyphenazine, pre-functionalized certain nitroethylenes or tetrazolyl radical.

This method is illustrated in Example 4 below.

In addition, there is the possibility of obtaining some of the compounds according to the present invention from other compounds according to the present invention (the difference in the nature of the R substituent).

Thus, according to the second aspect of the present invention is also possible to obtain:

the compounds of formula (I), where:

and Het is as defined above (in General),

through recovery under mild conditions corresponding compounds (Het has the same values) of the formula (I), where:

;

the compounds of formula (I), where:

and Het is as defined above (in General),/p>

by hydrolysis of the corresponding compounds of formula (I), where R=-NO2pick hydroxyphenazine formula (I'):

with the subsequent interaction of the primary environment obtained hydroxyphenazine with dinitropropanol ether. Consider the reaction scheme below:

This approach can complement the diagram on p.8. The second stage is similar to stage above.

The compounds of formula (I) (the new compounds according to the present invention + 3-nitro-4-(4-nitro-1,2,3-triazole-1-yl)furazan), as defined above, as a rule, actually, even especially, being obtained according to the methods described above, have properties that are quite exceptional with regard to stability and vulnerability. Their properties are useful when applied in the field of propellants and explosives. They have obvious advantages in comparison with competitors in relation to traditional energy molecules nitroamines type, such as HMX (octogen (NMH)) or CL20 (hexanitrohexaazaisowurtzitane).

In accordance with a third aspect of the present invention, the present invention relates to energetic compositions comprising (effective amount) by men who she least one connection, selected from the compounds of formula I (compounds according to the present invention, as defined above, and 3-nitro-4-(4-nitro-1,2,3-triazole-1-yl)furazan).

The definition of the effective number is the prerogative of the person skilled in the art depending on the particular end result for the energy of the composition. Energy compositions can contain, in particular, the composition of explosives or composition of rocket fuel. These two types of energy songs (with traditional energy molecules) are well known to specialists in this field of technology.

The energy of the composition according to the present invention relating to the first type (composition of explosives), contain or do not contain a binder material (inert or energetic). Typically, they consist of at least 20 wt.% (preferably at least 50 wt.%) at least one compound selected from compounds of formula (I) according to the present invention and 3-nitro-4-(4-nitro-1,2,3-triazole-1-yl)furazan, in General they consist of at least 20 wt.% (preferably at least 50 wt.%) such compounds selected from compounds of formula (I) according to the present invention and 3-nitro-4-(4-nitro-1,2,3-triazole-1-yl)furazan. They (the songs) can consist of b is more than 95 wt.% and even on 100 wt.% of the at least one connection selected from compounds of formula (I) according to the present invention + 3-nitro-4-(4-nitro-1,2,3-triazole-1-yl)furazan.

It should also be noted that some compounds according to the present invention can be obvious potential components insensitive compositions of explosives type MURAT (MURAT, MUnition with Risk ATtenuation) instead of RDX (cyclonite = cyclobutanemethanamine, hexogen = cyclomethylenetrinitramine).

The energy of the composition according to the present invention related to the second type (composition of rocket fuel), contain neutral or energetic binder material. As a rule, they contain not more than 80 wt.% (preferably between 50 and 80 wt.%) at least one compound selected from compounds of formula (I) according to the present invention and 3-nitro-4-(4-nitro-1,2,3-triazole-1-yl)furazan, most often more than 80 wt.% (preferably between 50 and 80 wt.%) compounds selected from compounds of formula (I) according to the present invention and 3-nitro-4-(4-nitro-1,2,3-triazole-1-yl)furazan.

Further, the present invention is illustrated with examples.

Received six compounds of formula (I) (see Table 1 below).

You should pay attention to the properties of the obtained compounds, and their technical characteristics (see Tables 2 and 3 below).

Examples of OS is ENFORCED INVENTIONS

Example 1

5 ml of anhydrous acetonitrile are placed in a dry three-neck flask in an argon atmosphere, and then add a 32.6 mg (1,358 mmol) of NaH and 154 mg (1.35 mmol) of 3-nitro-1,2,4-triazole, the resulting mixture was stirred at ambient temperature for 15 minutes to complete the formation of the anion nitrotriazole. At the same time add the entire sample dinitropropanol ester (300 mg, of 1.23 mmol) and then stirred the resulting medium at ambient temperature for 20 hours. Then add 20 ml of water. The reaction product is extracted with chloroform and the chloroform extract is dried over magnesium sulfate, filtered, and then evaporated chloroform. The reaction product is purified on silica gel. Thus obtain 194 mg of pure product (yield 63%).

Expanded formula of the obtained compound, and the results of physico-chemical analyses (1H,13C and14N NMR), confirming the structure shown in the first column of Table 1.

Example 2

5 ml of anhydrous acetonitrile are placed in a dry three-neck flask in an argon atmosphere, and then add 165,4 mg (1,03 mmol) dinitropropane and 117,1 mg (1,008 mmol) 3-nitro-1,2,4-triazole. Then to the reaction medium at a temperature of 20°C are added dropwise 3 ml of pyridine (92 mg), diluted with acetonitrile. The resulting medium is stirred at ambient temperature T. the value of 5 hours. Then add 20 ml of water. The reaction product is extracted with chloroform and the chloroform extract is dried over magnesium sulfate, filtered, and then evaporated chloroform. The reaction product is purified on silica gel. Thus obtain 56 mg of the pure product (yield relatively dinitropropane is 24%).

The resulting product is the same as the product obtained according to Example 1 (see the first column of Table 1).

Example 3

2,05 g aminocyclopropane (15 mmol) is added at a temperature between 0 and 5°C, to a solution of concentrated sulfuric acid (12 ml) and concentrated phosphoric acid (12 ml). Then small portions add sodium nitrite (1.10 g, 15.8 mmol). To the reaction medium simultaneously add the entire sample nitroacetanilide 1,64, the Reaction medium was no longer stirred for one hour and then poured onto 40 g of ice. Allocation deposition occurs within a few hours, and then the intermediate product is filtered, washed with water and dried over P2O5. 0,46 g pre-obtained dry product was placed in 15 ml of distilled water. Then to the resulting solution at a temperature of 20°C, slowly add 0.75 ml of acetic anhydride and support is a pH of 7 by adding 5% sodium hydroxide solution. At the end add the medium is acidified using 10% of rest the p HCl. The reaction product is extracted with ethyl acetate, the extract is dried over magnesium sulfate, filtered and then evaporated ethyl acetate. The reaction product is purified on silica gel. Thus obtain 72 mg of pure product (yield 2%).

Expanded formula of the obtained compound, and the results of physico-chemical analyses (1H,13C and14N NMR), confirming its structure is given in the second column of Table 1.

Example 4

3-Hydroxy-4-(4-nitro-1,2,3-triazole-2-yl)furazan get from aminohydroxylation according to the procedure described in Example 3. 5 ml of anhydrous acetonitrile are placed in a dry three-neck flask in an argon atmosphere, and then add 264,7 mg (1,34 mmol) 3-hydroxy-4-(4-nitro-1,2,3-triazole-2-yl)furazan and 39 mg (of 1.62 mmol) of sodium hydride. Then the reaction medium was heated to 40°C and quickly add dinitropropanol ether (323 mg). The resulting medium is refluxed for 6 hours. Then add 20 ml of chloroform. Salt deposited precipitates, is filtered off. Wednesday concentrated under vacuum, and then the reaction product is purified on silica gel. Thus obtain 170 mg of pure product (yield 56%).

Expanded formula of the obtained compound, and the results of physico-chemical analyses (1H,13C and14N NMR), confirming the structure shown in the third column of Table 1.

Example 5

0.5 g asianfreesexvideos (of 1.87 mmol) was injected in 10 ml of dioxane in the presence 0,22 g of sulfuric acid. Then add 0.35 g morpholinosydnonimine. The mixture is heated to 80°C for 2 hours, and then evaporated the solvent. The crude product is purified on silica gel. Thus receive 60 mg of pure product (yield of 9.5%).

Expanded formula of the obtained compound, and the results of physico-chemical analyses (1H,13C and14N NMR), confirming the structure shown in the fourth column of Table 1.

Example 6

20 ml of anhydrous acetonitrile are placed in a dry three-neck flask in an argon atmosphere, and then add 600 mg dinitropropane (3.75 mmol) and 592 mg (3.75 mmol) of 3,4-dinitrophenol. Then to the reaction medium at a temperature of 20°C is added dropwise 10 ml of a solution of pyridine (296 mg, 3.75 mmol), dissolved in acetonitrile. The resulting medium at ambient temperature stirred for 5 hours. Then add 20 ml of water. The reaction product is extracted with chloroform and the chloroform extract is dried over magnesium sulfate, filtered, and then evaporated chloroform. The reaction product is purified on silica gel. Thus receive 300 mg of pure product (yield 30%).

Expanded formula of the obtained compound, and the results of physico-chemical analyses (1H,13C and14/sup> N NMR), confirming the structure shown in the fifth column of Table 1.

Example 7

20 ml of anhydrous acetonitrile are placed in a dry three-neck flask in an argon atmosphere, and then add 463 mg dinitropropanol ether (1,90 mmol) and 300 mg (1,90 mmol) of 3,5-dinitrophenol. Then to the reaction medium at a temperature of 20°C is added dropwise 10 ml of a solution of pyridine (150 mg, 1,90 mmol)dissolved in acetonitrile. The resulting medium at ambient temperature stirred for 3 days. Then add 20 ml of water. The reaction product is extracted with chloroform and the chloroform extract is dried over magnesium sulfate, filtered, and then evaporated chloroform. The reaction product is purified on silica gel. Thus obtain 45 mg of pure product (yield of 8.7%).

Expanded formula of the obtained compound, and the results of physico-chemical analyses (1H,13C and14N NMR), confirming the structure shown in the fifth column of Table 1.

Table 1 below.

In addition, the structure of the products obtained in the Examples:

1 and 2: 3-nitro-4-(3-nitro-1,2,4-triazole-1-yl)furazan and

3: 3-nitro-4-(4-nitro-1,2,3-triazole-2-yl)furazan was confirmed by x-ray diffraction analysis.

The results obtained are shown on the attached Figure 2, and 1 respectively.

Also the trail is t to draw attention to the properties and technical characteristics of products (compounds) according to the present invention, obtained in Examples 1-7, above.

(a) Sensitivity and thermal stability

The sensitivity of the products according to the present invention in comparison with the sensitivity NMH and HNIW (NMH = HMX, HNIW = CL20 = hexanitrohexaazaisowurtzitane) determine in relation to external influences mechanical and electrostatic types by dynamic loads, friction and spark research.

Research carried out as described below.

Sensitivity to dynamic loading: the investigations described in standard NF T 70-500, a technique which is similar to UNO test 3a) (ii) of the “Recommendations on the Transport of Dangerous Goods - Manual of Tests and Criteria, Fourth revised edition, ST/SG/AC.10/11/Rev.4, ISBN 92-1-239083-8ISSN 1014-7179”. The amount of energy, in which the number of positive results for explosive materials subjected to dynamic loads through the load is 50% (Brusenskii processing method results)is determined by carrying out at least a series of 30 trials. The investigated material is placed in the device, made of steel and provided with two rollers and the guide ring. By changing the mass and drop height of cargo can vary the energy from 1 to 50 joules. Due to the fact that for some of the investigated products available small quantity is of material for such products carry a reduced number of reproducible research in comparison with the recommendations specified in the normative document NF T 70-500.

Sensitivity to friction: an Ongoing study described in the standard NF T 70-503, a technique which is similar to UNO 3b) (ii). The force at which the number of positive results for explosive material, subjected to friction, is 50%, is determined by carrying out at least a series of 30 trials using Brusenskii method. The investigated material is placed on a porcelain plate with a certain (desired) roughness, which result in reciprocating motion with an amplitude of 10 mm and speed without load 7 cm/s relative to the porcelain column, based on the material. Force applied to the porcelain column, which relies on the material, can be varied from 7.8 to 353 N. Due to the fact that for some of the investigated products available a small amount of material for such products carry a reduced number of reproducible research in comparison with the recommendations specified in the normative document NF T 70-503.

Sensitivity to ignition by electric sparks: an ongoing study is a study developed by company C is the revealer, and has no NF or UNO equivalents. The analyzed material is placed in the Cup-shaped container with a diameter of 10 mm and height 1.5 mm, have between two electrodes and exposed to electric sparks of different energies from 5 to 726 MJ. Watching going to happen or not pyrotechnic explosion, and determines the energy threshold at which the material no longer ignites. This is confirmed by conducting 20 successful trials. Due to the fact that for some of the investigated products available a small amount of material for such products carry a reduced number of reproducible research.

Thermal stability for their part shall be determined as follows.

Thermal stability: thermal stability analyzed by the method of differential thermal analysis (Differential Thermal Analysis (DTA or DSC)). Differential thermal analysis (DTA) is to determine the characteristics of the product in a certain (given) temperature range through the study of heat exchange with the transformations and reactions, which occurs when the product is exposed to high temperature. Junction temperature determined by the change in heat flow, used to heat the sample. This method allows to distinguish between the melting temperature (Tp is ), boiling point (TKip) and decomposition temperature (TFS).

The results obtained are presented in Table 2.

Analyzing the results, shown in Table 2, it is possible to give the following comments:

Compounds according to the present invention exhibit relatively low sensitivity values in different studies. It should be noted that the sensitivity of the ether (the compound described in Example 4), has the same order as the sensitivity monourethane (compounds described in Examples 1, 2, 3, 6 and 7). Sensitivity ethoxypropanol (compound described in Example 5) is more important than for other forzano. It should also be noted that some compounds according to the present invention (this does not apply to ethoxypropionate according to Example 5) are insensitive to friction, exactly the same as "insensitive" molecules, known to the specialist in the art from the prior art: NTO (5-nitro-1,2,4-triazole) and TATTWAS (1,3,5-triamino-2,4,6-trinitrobenzene).

Compounds according to the present invention show very good thermal stability. New furutani show signs of decomposition at around 200°C. In some cases, energy products melt and then spraydate higher temperatures without the occurrence of a minimal decomposition. This testifies to the exceptional thermal stability of such compounds.

b) specifications

Energy levels products according to the present invention is determined by calculating the density and enthalpy of formation.

Then technical characteristics calculated during the explosion and engine installation for applications as a simple component of rocket fuel (0% ammonium perchlorate and 0% aluminum), in the presence of plasticizing binder materials with nitrated oils. The polymer components such binders are energy type (poly(glycidylether): PGA) or inert type, for example, of polyethers (NTREE = hydroxyalkyl polyester). The ratio used to predict the technical characteristics of the rocket fuel component is 85/15 (charge/binder). For explosives and propellants samples represent HMX (NMH) and 8-hexanitrohexaazaisowurtzitane h (ε-CL-20 = ε-HNIW).

The results are shown in Table 3.

The results demonstrate the advantages of the compounds according to the present invention.

of 124.1
Table 3
Connection Enthalpy of formation (kcal/mol)DensityEnergy blast (V/Vo=2)*A simple component of rocket fuel
Charge/PGA (85/15) SI (C)
A simple component of rocket fuel
Charge/NTRE (85/15) SI (C)
NMH20,11,908100% NMH260,4249,9
Examples 1 and 2123,31,884102% NMH264,6253,8
Example 3158,51,884111% NMH276,3267,2
Example 4209,41,921112% NMH273,2263,2
Example 5272,41,954120% NMH278,7269,4
Example 61,934110% NMH270,5261,8
Example 7of 124.11,936110% NMH270,5261,8
ε-CL2091,52,04120% NMH268,0260,1
*The released energy of detonation, kinetic and internal to the degree of extension products to double the volume compared to the initial volume

1. The compound of formula (I)

where R=-NO2,
,or;
and Het represents solely radical selected from nitroanaline and tetrazolyl radicals;
with the exception of 3-nitro-4-(4-nitro-1,2,3-triazole-1-yl)furazan.

2. The compound according to claim 1 of formula (I), wherein Het represents solely radical selected from unsubstituted (bi)tetrazolyl radicals and (b)pyrrolidine, (b)pyrazolidine, (b)triazolyl and (b)tetrazolyl radicals, Sames is, R is at least one nitro-group.

3. The compound according to claim 1 of formula (I), wherein Het is chosen from nitrotriazole; dinitrocresols; dinitropyridine; tetrazolyl; 5-nitrotetrazolium; bi(nitropyrrole); literatlly; bi(nitro)triazolyl and bi(dinitropropyl) radicals.

4. The compound according to claim 1 of formula (I), wherein Het is chosen from the following radicals:
- 3-nitro-1,2,4-triazole-1-yl,
- 4-nitro-1,2,3-triazole-2-yl,
- 4-nitro-1,2,3-triazole-1-yl,
- 3,4-dinitrobenzoyl,
- 3,5-dinitrobenzoyl,
- 1,2,3,4-tetrazol-1-yl.

5. The compound according to claim 1 of formula (I), characterized in that it is chosen from:
- 3-nitro-4-(3-nitro-1,2,4-triazole-1-yl)furazan,
- 3-nitro-4-(4-nitro-1,2,3-triazole-2-yl)furazan,
- 4-nitro-4'-(4-nitro-1,2,3-triazole-2-yl)misfortunately ester,
- 4-nitro-4'-(4-nitro-1,2,3-triazole-1-yl)-3,3'-ethoxysulfuron,
- 3-nitro-4-(3,4-dinitrobenzoyl)furazan,
- 3-nitro-4-(3,5-dinitrobenzoyl)furazan.

6. A method of obtaining a compound as defined in any one of claims 1 to 5, characterized in that it comprises the reaction of interaction nitrofurazone formula (IIa)

where R is as defined in claim 1, and
Azola formula (IIb):

where Het is as defined in any one of claims 1 to 4,
by means of nucleophilic substitution in a polar organic medium and in the presence of the basis of the Oia.

7. A method of obtaining a compound as defined in any one of claims 1 to 4,

where Het is as defined in any one of claims 1 to 4, characterized in that it includes recovery under mild conditions corresponding compounds of formula (I),

8. A method of obtaining a compound as defined in any one of claims 1 to 4,

where Het is as defined in any one of claims 1 to 4, characterized in that it comprises the hydrolysis of the corresponding compounds of formula (I), where R=-NO2obtaining hydroxyphenazine formula (G):

with the subsequent interaction of the primary environment specified hydroxyphenazine with dinitropropanol ether.

9. Energy composition, characterized in that it comprises an effective amount of at least one compound selected from compounds of formula (I)as defined in any one of claims 1 to 5.

10. Energy composition according to claim 9, characterized in that it comprises at least 20 wt.% at least one compound selected from compounds of formula (I)as defined in any one of claims 1 to 5.

11. Energy composition according to claim 9, characterized in that it includes not more than 80 wt.% at least one compound selected from compounds of formula (I), as they op is edeleny in any one of claims 1 to 5, in the binder material.



 

Same patents:

FIELD: chemistry.

SUBSTANCE: invention describes isoxazolines of formula (I), in which A denotes C or N; R denotes C1-4 haloalkyl; X denotes identical or different halogens or C1-4 haloalkyl; l equals 0, 1 or 2; Y denotes halogen or C1-4 alkyl, C1-4alkoxy, C1-4haloalkyl, cyano, nitro, amino, C1-4 alkylcarbonylamino, benzoylamino or C1-4 alkoxycarbonylamino; m equals 1 or 1; and G denotes any group selected from heterocyclic groups given in the description, and a method of producing said compounds and use as insecticides for controlling the population of harmful insects or arthropods.

EFFECT: high efficiency of using said compounds.

11 cl, 28 ex, 4 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to novel azoles of general formula 1A and 1B and pharmaceutically acceptable salts thereof, having activity on hepatitis C and hepatitis GBV-C virus. Said compounds have NS5A viral protein ligand properties and can be used as active components for a pharmaceutical composition and a medicinal agent for treating diseases caused by said viruses. In general formula 1A and 1B, the solid lines accompanied by dotted lines denote a single or double bond, wherein if one of them is a single bond, the other is a double bond; X and Y optionally assume different values and denote a nitrogen, oxygen or sulphur atom or a NH group; R1 and R2 optionally denote identical radicals 2.1-2.20, in which the asterisk (*) indicates site of the bond to azole fragments. Said fragments and values of A and B are given in the claim.

EFFECT: more value of the compounds.

10 cl, 1 tbl, 16 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: this invention relates to new compounds with formula (I) possessing the properties of mGLuR2 antagonists, to their obtainment methods, their application for production of medicines for prevention and treatment of disorders wherein mGLuR2 plays the activation role (in particular - central nervous system disorders). In formula (I) either any of X and Y represents N while the other represents CH or each of X and Y represents N; A represents aryl representing phenyl or 5- or 6-membered heteroaryl containing in the cycle 1-3 atoms selected from among nitrogen, oxygen or sulphur, the heteroaryl selected from among amidazolyl, [1,2,4] oxadiazolyl, pyrrolyl, 1H-pyrazolyl, pyridinyl, [1,2,4] triazolyl, tiazolyl and pyrimidinyl, each of them substitutable by C1-6-alkyl; B represents H, cyano or represents a possibly substituted aryl selected from among phenyl or possibly substituted by 5- or 6-membered heteroaryl containing in the cycle 1-3 atoms selected from among nitrogen, oxygen or sulphur where the substitutes are selected from the group consisting of nitro, C1-6-alkyl, possibly substituted hydroxy, NRaRb where Ra and Rb independently represent H, C1-6-alkyl etc. R1 represents H, a halogen atom, C1-6-alkyl, possibly substituted hydroxy, C1-6-alcoxy, C1-6-halogenoalkyl, C3-6-cycloalkyl represents H cyano, a halogen atom, C1-6-halogenoalkyl, C1-6-alcoxy, C1-6-halogenoalcoxi-, C1-6-alkyl or C3-6-cycloalkyl R3 represents a halogen atom, H, C1-6-alcoxy, C1-6-halogenoalkyl, C1-6-alkyl, C3-6-cycloalkyl, C1-6-halogenoalcoxy R4 reprsents H or halogeno.

EFFECT: creation of new compounds of formula (I) possessing mGLuR2 antagonist properties.

104 cl, 465 ex

FIELD: chemistry.

SUBSTANCE: invention relates to novel compounds of formula (I)

, where: n equals 0, 1, 2; G denotes CH2, CHR3; R1 denotes H, C1-C6-alkyl, C3-C6-alkenyl, -CH2Ph; R2, R3, R4 independently denote H, CH3, -CH2F, -CHF2, CF3; A denotes 1,4-Ph, 1,3-Ph, which can be optionally substituted with 1-4 substitutes selected from halogen, C1-C4-alkyl, C1-C4alkoxy, fluorinated C1-C4-alkyl and fluorinated C1-C4alkoxy; E denotes NR5, where R5 denotes H, C1-C3-alkyl; Ar denotes a radical of formula

and

where: Ra denotes halogen, C1-C6-alkyl, fluorinated C1-C6-alkyl, C1-C6-alkoxy, fluorinated C1-C6-alkoxy, phenyl sulphonyl, CN, -NR6R7, where R6 and R7, together with an N atom, form a 5- or 6-member saturated ring or denotes a 5-member saturated or unsaturated aromatic or non-aromatic heterocyclic ring containing, as ring members, 1, 2 or 3 heteroatoms selected from N, O and S, and where the heterocyclic ring can carry 1, 2 or 3 substitutes selected from halogen and C1-C6-alkyl, or denotes a 6-member saturated heterocyclic ring containing, as ring members, one N and one O atom; Rb and Rc independently denote H, halogen, CH3, OCH3, CH2F, OCH2F, CHF2, OCHF2, CF3, OCF3, CH2CH2F, OCH2CH2F, CH2CHF2, OCH2CHF2, CH2CF3 or OCH2CF3; Rd denotes Ra or a 5- or 6-member heteroaromatic ring containing, as ring members, 1, 2 or 3 heteroatoms selected from N, O and S, and where the heteroaromatic ring can carry 1 substitute selected from C1-C6-alkyl and C1-C6-alkylthio; Re denotes H or is defined as Ra; Rf is defined as Ra; k equals 0, 1, 2, 3; j equals 0, 1, 2, 3, 4; provided that Ra does not denote F, CH2F, CHF2, CF3, OCF3, if A denotes 1,4-Ph, Ar denotes a radical of formula (A) and Rb and Rc denote H, halogen; except compounds, where R1 denotes propyl, G denotes CH2, n equals 1, A denotes 1,4- Ph, E denotes NH, Ar denotes a radical of formula (F) and Rd denotes halogen, C1-C6-alkyl, C2-C6-alkenyl or a 5-member heteroaromatic ring; and physiologically acceptable acid addition salts thereof.

EFFECT: compounds exhibit 5HT6 receptor simulating activity, which allows for their use in a pharmaceutical composition.

25 cl, 6 tbl, 107 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to compounds specified in cl. 1, and also to a pharmaceutical composition possessing binding activity with respect to Bcl proteins, to applying the declared compounds for preparing a drug for treating cancer and for treating a bcl-mediated disorder.

EFFECT: use of the compounds as Bcl protein inhibitors.

18 cl, 2 tbl, 41 ex

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of general formula where R1, R2 and R3 are independently selected from a group consisting of hydrogen, halogen and lower alkyl containing 1-6 carbon atoms; R4 denotes a residue given in the claim; R5 denotes hydrogen or methyl; R10 is selected from a group consisting of: (i) hydrogen; (ii) (C1-C10) alkyl; (iii) (C1-C10)alkyl, substituted with one or more substitutes independently selected from a group consisting of -N(CH3)2, morpholinyl, (C1-C4) alkoxy, hydroxyl, -CON(CH3)2 and halogen; (iv) monocyclic (C3-C8) cycloalkyl containing one N heteroatom; (v) 9-methyl-9-azabicyclo[3.3.1]nonane; (vi) phenyl; (vii) phenyl substituted with one or more (C1-C4)alkoxy; R11 is selected from a group consisting of hydrogen and (C1-C10)alkyl; or R10, R11 and a nitrogen atom with which they are bonded, together, form a nitric heterocycle or a substituted nitric heterocycle, such as given in the claim. The invention also relates to a pharmaceutical composition, having serotonin type 3 receptor modulating capacity and a method of treating a disorder which depends on serotonin type 3 receptor modulation.

EFFECT: compounds of formula II as serotonin type 3 receptor modulators.

18 cl, 1 tbl, 159 ex

FIELD: chemistry.

SUBSTANCE: invention describes a compound of formula (I): or pharmaceutically acceptable salt thereof, or stereoisomer, in which: n equals 0 or 1; X denotes CH2, C=O; R1 denotes a) -(CH2)mR3 or -CO(CH2)mR3, where m equals 0, 1; and R3 denotes a 5-10-member aryl or heteroaryl, where the heteroaryl denotes a mono- or bicyclic aromatic ring containing 5-10 ring atoms, from which at least one or two atoms are heteroatoms selected oxygen, nitrogen or sulphur, optionally substituted with one or more halogens; b) -C=YR4, where Y denotes O; and R4 denotes: (C1-C10)alkyl; (C1-C10)alkoxy; (C0-C10)alkyl-(5-10-member heteroaryl), where "heteroaryl" denotes a mono- or bicyclic aromatic ring containing 5-10 ring atoms, from which at least one or two atoms are heteroatoms selected from oxygen, nitrogen or sulphur, said heteroaryl is optionally substituted with one or more substitutes selected from halogen, oxo or 2-(C1-C6)alkyl, where Z denotes S; (C0-C10)alkyl-(5-10-member aryl), said aryl is optionally substituted with one or more substitutes selected from halogen; (C1-C6)alkoxy, which itself is optionally substituted with one or more halogens; (C1-C6)alkyl, which itself is optionally substituted with one or more halogens; or -Z-(C1-C6)alkyl, where Z denotes S or SO2, and where said (C1-C6)alkyl can be optionally substituted with one or more halogens; or (C1-C6)alkyl-CO-O-R12, where R12 denotes H or (C1-C6)alkyl; or c) -C=ZNHR6, where Z denotes O or S; and R6 denotes: (C1-C10)alkyl; (C1-C10)alkoxy; 5-10-member aryl or heteroaryl, where "heteroaryl" denotes a bicyclic aromatic ring containing 9 ring atoms, from which at least one or two atoms are oxygen atoms; optionally substituted with one or more substitutes selected from halogen; cyano; (C1-C6)alkoxy, which itself is optionally substituted with one or more halogens; (C1-C6)alkyl, which itself is optionally substituted with one or more halogens; and R2 denotes H or (C1-C6)alkyl. Also described is a pharmaceutical composition for inhibiting TNFα, based on the compound of formula I.

EFFECT: novel compounds which can regulate production of certain cytokines, including TNF-α, are obtained and described.

27 cl, 81 ex, 1 tbl

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to new compounds of formula (IB) or to their pharmaceutically acceptable salts:

, wherein R means formula: R1 means -C(O)NR3R4, -C(O)R3 and -C(O)OR3; each R3 and R4 independently means H, C1-10 alkyl, wherein alkyl is optionally substituted by one -OH; R3 and R4 are bound together with N atoms to form a 5-6-member heterocyclic ring which additionally contains one O heteroatom; R5 means H; R6 means CN; R7 means H; W means C. What is described is a method for producing both them and intermediate compounds of formula (1-1c): , wherein: R1 means -C(O)NR3R4; R3 and R4 are specified above.

EFFECT: compounds (IB) shows DPP-IV inhibitory activity that allows them being used in a pharmaceutical composition.

9 cl, 12 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: present invention refers to compounds of general formula (I) or its pharmaceutically acceptable salts which have action of mTOR inhibitors. What is also declared is preparing a pharmaceutical composition containing a therapeutically effective amount of the compound of formula (I) and a pharmaceutically acceptable carrier or diluent; besides, what is declared is the use of the compound of formula (I) or its pharmaceutically acceptable salts for preparing the drug for ensuring anticancer action.

EFFECT: preparing the pharmaceutically acceptable salts for preparing the drug for ensuring anticancer action.

11 cl, 25 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to a compound of formula I wherein the substitutes A, B, B', Q and R1-R5 in formula I are specified as follows: A and B' are one of the following groups: (i) (R6)N(CH2)n, wherein n is 0 or 1; (ii) (CH2)n, wherein n is 0, 1 or 2; (iii) C(O)(CH2)n, wherein n is 0 or 1; or provided each of A and B' represents nitrogen, together they can form a bivalent radical of formula: -(CH2)s-X1-(CH2)t- (a), wherein each s and t is independently 1 or 2, and X1 represents (CH2)n, wherein n is 0 or 1; B is one of the following groups: (i) (R6)N; (ii) oxygen; (iii) C=δ, wherein δ represents oxygen or sulphur; (iv) C(R6)=C(R7); each R6 and R7 independently represent hydrogen, C1-4-alkyl; R1 is specified in the following groups: (i) phenyl group substituted by one or more substitute such as: - halogen specified in F, CI, Br or I, or alkyl1 group; aryl1 or heteroaryl group1; cyano, NH-alkyl1, N(alkyl1)(alkyl1) and amino; - NHCO-R or NHCOO-R, or COO-R, or CONH-R, wherein R represents hydrogen or alkyl group, or (ii) pyridinyl group which can be substituted by one substitute, such as halogen specified in I, F, Cl or Br; alkyl1 group; aryl1 group; cyano, NH-alkyl1, N(alkyl1)(alkyl1), and amino; -NHCO-R or NHCOO-R, or COO-R, or CONH-R, wherein R represents hydrogen or alkyl1 group; each R2, R3, R4 and R5 are independently specified in hydrogen or linear or branched alkyl group containing 1 to 10 carbon atoms; Q is specified in the following groups: (i) alkyl1; (ii) aryl1; (iii) heteroaryl1. The compounds of formula (I) are used for preparing a drug showing the c-kit inhibitor properties and aiming at treating a disease specified in neoplastic, allergic, inflammatory and autoimmune diseases.

EFFECT: use of oxazole derivatives as tyrosine kinase inhibitors.

13 cl, 1 tbl, 31 ex

FIELD: chemistry.

SUBSTANCE: invention describes isoxazolines of formula (I), in which A denotes C or N; R denotes C1-4 haloalkyl; X denotes identical or different halogens or C1-4 haloalkyl; l equals 0, 1 or 2; Y denotes halogen or C1-4 alkyl, C1-4alkoxy, C1-4haloalkyl, cyano, nitro, amino, C1-4 alkylcarbonylamino, benzoylamino or C1-4 alkoxycarbonylamino; m equals 1 or 1; and G denotes any group selected from heterocyclic groups given in the description, and a method of producing said compounds and use as insecticides for controlling the population of harmful insects or arthropods.

EFFECT: high efficiency of using said compounds.

11 cl, 28 ex, 4 tbl

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention relates to a compound with formula (I): where the values of radicals Q, R1, R2, R3, R4, X and Y are as specified in Clause 1 of the patent claim or to a pharmaceutically acceptable salt of such compound or a compound ether hydrolysed in vivo provided such compound is not: {(3S)-1-[5-(adamantan-1-ylcarbamoyl)pyridine-2-yl] piperidine-3-yl} acetic acid or {(3S)-1-[5-(cyclohexylcarbamoyl)-6-(piperazine-1-yl) pyridine-2-yl] piperidine-3-yl} acetic acid or a pharmaceutically acceptable salt thereof or a compound ether hydrolysed in vivo. Additionally, the invention relates to a pharmaceutical composition containing a compound with formula I for treatment of metabolic syndrome, Type II diabetes, adiposity etc and to application of such compound with formula I for manufacture of a medication to be applied for causing an inhibition effect with regard to 11βHSD1 with a homoiothermal animal.

EFFECT: produced and described is a new compound possessing inhibition activity with regard to Type 1 human 11-β-hydroxisteroiddehydrohenase enzyme (11βHSD1).

15 cl, 187 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: this invention relates to new compounds with formula (I) possessing the properties of mGLuR2 antagonists, to their obtainment methods, their application for production of medicines for prevention and treatment of disorders wherein mGLuR2 plays the activation role (in particular - central nervous system disorders). In formula (I) either any of X and Y represents N while the other represents CH or each of X and Y represents N; A represents aryl representing phenyl or 5- or 6-membered heteroaryl containing in the cycle 1-3 atoms selected from among nitrogen, oxygen or sulphur, the heteroaryl selected from among amidazolyl, [1,2,4] oxadiazolyl, pyrrolyl, 1H-pyrazolyl, pyridinyl, [1,2,4] triazolyl, tiazolyl and pyrimidinyl, each of them substitutable by C1-6-alkyl; B represents H, cyano or represents a possibly substituted aryl selected from among phenyl or possibly substituted by 5- or 6-membered heteroaryl containing in the cycle 1-3 atoms selected from among nitrogen, oxygen or sulphur where the substitutes are selected from the group consisting of nitro, C1-6-alkyl, possibly substituted hydroxy, NRaRb where Ra and Rb independently represent H, C1-6-alkyl etc. R1 represents H, a halogen atom, C1-6-alkyl, possibly substituted hydroxy, C1-6-alcoxy, C1-6-halogenoalkyl, C3-6-cycloalkyl represents H cyano, a halogen atom, C1-6-halogenoalkyl, C1-6-alcoxy, C1-6-halogenoalcoxi-, C1-6-alkyl or C3-6-cycloalkyl R3 represents a halogen atom, H, C1-6-alcoxy, C1-6-halogenoalkyl, C1-6-alkyl, C3-6-cycloalkyl, C1-6-halogenoalcoxy R4 reprsents H or halogeno.

EFFECT: creation of new compounds of formula (I) possessing mGLuR2 antagonist properties.

104 cl, 465 ex

FIELD: chemistry.

SUBSTANCE: invention relates to novel substituted cyclohexylmethyl derivatives, having serotonin, noradrenaline or opioid receptor inhibiting activity, optionally in form of cis- or trans-diastereomers or mixture thereof in form of bases or salts with physiologically compatible acids. In formula (1): R2 denotes H or OH; R1 and R2 together denote or =N-OH, R3 denotes a phenyl residue which is unsubstituted or monosubstituted with a halogen atom or a heteroaryl residue selected from a five-member sulphur-containing heteroaryl such as a thienyl residue or an unsubstituted phenyl residue bonded through a C1-C4alkyl group, R4 and R5 independently denote an unsubstituted C1-C3alkyl or R4 and R5 together denote (CH2)3-6, R8 denotes a linear saturated C1-C4 alkyl group bonded with an aryl, which is unsubstituted or monosubstituted with halogen atoms, R9 denotes a saturated C1-C8alkyl; values of radicals R1, m, n, R6, R7, R10-R13 are given in the claim. The invention also relates to methods of producing compounds of formula (I), a medicinal agent containing said compounds, use of compounds of formula (I) to prepare a medicinal agent for anaesthetic treatment during sharp, neuropathic or chronic pain and for treating depression, urinary incontinence, diarrhoea and alcoholism.

EFFECT: high efficiency of using the compounds.

32 cl, 501 ex, 21 tbl

FIELD: chemistry.

SUBSTANCE: invention describes compounds of formulae (I) and (III), as well as isomers or pharmaceutically acceptable salts thereof: where the values of radicals are given in claim 1 and 5. The invention also relates to a pharmaceutical composition based on said compounds, which has vanilloid receptor antagonist activity, use of said compounds to produce a medicinal agent for preventing or treating a condition which is associated with aberrant expression and/or aberrant activation of the vanilloid receptor. Described also is a method of producing a compound of formula III.

EFFECT: novel compounds which can be used as vanilloid receptor antagonists, for preventing or treating diseases are obtained and described.

40 cl, 281 ex, 3 tbl

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to pyridine derivatives of formula

wherein A, R1, R2, R3, R4, R5 and R6 are presented in the description, preparing and using them as pharmaceutically active compounds as immunomodulatory agents.

EFFECT: preparing the pharmaceutical composition showing agonist activity with respect to S1P1/EDG1 receptor and using it for prevention and treatment diseases or disorders associated with activated immune system.

20 cl, 244 ex, 2 tbl

FIELD: medicine, pharmaceutics.

SUBSTANCE: present invention refers to heterocyclic compounds of formula ,

wherein X2 represents residue C-Z-R2 or C-R3, wherein Z represents NH or S; R1 is selected from structures , and R2 and R3 have the values specified in cl.1 of the patent claim, or to their pharmaceutically acceptable salts. The invention also refers to a pharmaceutical composition, a series of specific compounds, application of the declared compounds and to an intermediate compound for preparing the compounds of formula (I).

EFFECT: compounds under the invention have affinity to muscarine receptors and can be used in treating, relieving and preventing diseases and conditions mediated by muscarine receptors.

13 cl, 3 tbl

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to a compound of formula I wherein the substitutes A, B, B', Q and R1-R5 in formula I are specified as follows: A and B' are one of the following groups: (i) (R6)N(CH2)n, wherein n is 0 or 1; (ii) (CH2)n, wherein n is 0, 1 or 2; (iii) C(O)(CH2)n, wherein n is 0 or 1; or provided each of A and B' represents nitrogen, together they can form a bivalent radical of formula: -(CH2)s-X1-(CH2)t- (a), wherein each s and t is independently 1 or 2, and X1 represents (CH2)n, wherein n is 0 or 1; B is one of the following groups: (i) (R6)N; (ii) oxygen; (iii) C=δ, wherein δ represents oxygen or sulphur; (iv) C(R6)=C(R7); each R6 and R7 independently represent hydrogen, C1-4-alkyl; R1 is specified in the following groups: (i) phenyl group substituted by one or more substitute such as: - halogen specified in F, CI, Br or I, or alkyl1 group; aryl1 or heteroaryl group1; cyano, NH-alkyl1, N(alkyl1)(alkyl1) and amino; - NHCO-R or NHCOO-R, or COO-R, or CONH-R, wherein R represents hydrogen or alkyl group, or (ii) pyridinyl group which can be substituted by one substitute, such as halogen specified in I, F, Cl or Br; alkyl1 group; aryl1 group; cyano, NH-alkyl1, N(alkyl1)(alkyl1), and amino; -NHCO-R or NHCOO-R, or COO-R, or CONH-R, wherein R represents hydrogen or alkyl1 group; each R2, R3, R4 and R5 are independently specified in hydrogen or linear or branched alkyl group containing 1 to 10 carbon atoms; Q is specified in the following groups: (i) alkyl1; (ii) aryl1; (iii) heteroaryl1. The compounds of formula (I) are used for preparing a drug showing the c-kit inhibitor properties and aiming at treating a disease specified in neoplastic, allergic, inflammatory and autoimmune diseases.

EFFECT: use of oxazole derivatives as tyrosine kinase inhibitors.

13 cl, 1 tbl, 31 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to a compound of formula I

,

where A represents S or Se; B represents H or ; R1 represents aryl selected from the following structures:

R2 represents H or ; R3 represents H or C1-C8 alkyl; R4 and R5 independently represent H or C1-C8 alkyl; R6 represents H, C1-C8 alkyl, C2-C7 alkenyl, alkaline metal or alkaline earth metal; R11 and R12 independently represent H, C1-C8 alkyl or halogen; R21 represent H, halogen or C1-C7 alkyl; m and n independently represent integers having values 1-4; p represents an integer having a value of 1-5; q represents an integer having a value of 1-4; r represents an integer having a value of 1-3; s represents an integer having a value of 1-5; as an activator of peroxisome proliferator-activated receptor (PPAR) and its hydrate, solvate, stereoisomer and pharmaceutically acceptable salt, and to a pharmaceutical composition.

EFFECT: preparing an agent for muscle strengthening, an agent for memory improvement, a therapeutic agent for dementia and Parkinson's disease.

15 cl, 8 tbl, 348 ex

FIELD: chemistry.

SUBSTANCE: invention refers to new thiophene derivatives of formula (I) where A is represented by *-CO-CH2CH2-, *-CO-CH=CH, where the asterisks indicate the link through which the formula (I) thiophene group is bound; R1 is represented by C2-5alkyl; R2 is represented by hydrogen, methyl or ethyl; R3 is represented by hydrogen; R4 is represented by C1-4alkyl; R5 is represented by a hydroxy group, 2,3-di-hydroxypropoxygroup or -OCH2-CH(OH)-CH2-NHCOR52; R52 is represented by hydroxymethyl, and R6 is represented by C1-4alkyl; and to its salt. The invention also refers to the pharmaceutical composition that is agonistic in relation to S1P1/EDG1 receptor on the basis of the mentioned compounds.

EFFECT: new compounds and a composition based on them that may find their application in medicine as immunomodulating agents.

17 cl, 2 tbl, 44 ex

FIELD: chemistry.

SUBSTANCE: invention relates to explosives, particularly, to development of method of coating components of mixed solid-propellant rocket fuel. Modification of octogene is realized as follows: solution of polyethylene polyamine is prepared in methylene chloride and mixed at 20±5°C for 10-15 min. Octogene is added in tree steps at weight ratio of polyethylene polyamine and octogene to methylene chloride making 1:(5-7) for 15-20 min. Note here that octogene-to-polyethylene polyamine ratio makes 100:(0.03-0.05). Mixing is performed for 40-50 min at 20±5°C. Mix is cured at room temperature for 30 min, and dried at 70±5°C for 25-30 min.

EFFECT: better explosive, processing and strength characteristics.

2 tbl, 1 ex

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