Method for preparing adamant-1-yl-containing azoles

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to derivatives of adamantine, in particular, to a new method for preparing adamant-1-yl-containing azoles of the general formula I-VIII: wherein R1 means ; R2 means ; R3 means ; R4 means ; R5 means ; R6 means ; R7 means , and R8 means . Indicated derivatives of adamantine are semifinished products used in synthesis of biologically active substances. Proposed method for preparing these compounds involves using a new method for synthesis of adamant-1-yl-containing azoles that includes the addition reaction of azoles: 2-methylimidazole, 3(5)-methylpyrazole and 4-methylpyrazole, 3,4-dinitropyrazole, 1,2,4-triazole, 3-methylpyrazole, 3-nitro-1,2,4-triazole and 5-methyltetrazole to 1,3-dehydroadamantane in the mole ratio of 1,3-dehydroadamantane to azole = 1:1 in diethyl ether medium at temperature 100°C for 4-5 h.

EFFECT: improved preparing method.

8 ex

 

The invention refers to the chemistry of adamantane derivatives, and in particular to a new method of obtaining adamant-1-alsogaray azoles of the General formula

.,,,

,,,

which are intermediates for the synthesis of biologically active substances.

A method of obtaining adamant-1-alsogaray azoles: imidazoles, pyrazoles, triazoles and tetrazoles, which consists in using as starting reagents galogenarenov, 1-hydroxyadamantane or 1-nitrosoanabasine. When heated (190-200° (C) 1-bromoguanine with azoles in the presence of Lewis acids (AlCl3) output adamantylidene azoles is 45-75%. [Gassenheimer, Vpityu. Chemistry waterelemental. Part 2. Five-membered waterelemental. // Zhur.org.chem.. - 1990. - T.35. No. 2. - .183-220].

The disadvantage of this method is, first of all, the use of elevated temperatures (190-200° (C) and the presence of catalysts (AlCl3, TiCl3). The output at this adamantylidene azoles was 45-75%.

A method of obtaining azoles with adamantiades radical way of interaction the interaction of the number of azoles with adamantanol in the environment of 85%sulfuric acid for three days. Outputs adamant-1-alsogaray azoles did not exceed 33% [Ashevile, Allgood, Vol, Bigram. Adamantylidene. Acid-catalyzed adamantylamine pyrazoles. // Zhur.org.chem.. 2001. V.37. No. 12. S-1836].

The disadvantages of this method are: the use of concentrated sulfuric acid as catalyst, for quite a long time of synthesis, low product yield. Also in these conditions the reaction adamantylamine not take the imidazoles. For a successful synthesis it is necessary to choose a system that would combine education adamantinoma carbocation and incomplete protonation of imidazole.

There is a method of adamantylamine of imidazoles using acid system, consisting of a mixture of phosphoric and acetic acids with a ratio of 4:1 (mass.) [Ashevile, Allgood. Adamantylidene. Acid-catalyzed adamantylamine of nitroimidazoles. // Arr. 1999. T.35. No. 8. S-1261].

The disadvantages of this method is the low product yield, and studies have shown that the ability of the acid-catalyzed adamantylamine of imidazoles in a mixture of phosphoric and acetic acids is very limited because of the compounds of this series have a high basicity and almost completely proteinous in this system.

Common disadvantages of all these methods is the fact, they are not universal in the synthesis of adamant-1-alsogaray azoles: imidazoles, pyrazoles, triazoles, tetrazoles, low yields of the target products, the presence of a catalyst.

The task of the invention is to develop a versatile technology, milostivogo method of synthesis adamantylidene azoles proceeding with a high yield of the target product.

The technical result is a simplification of the production method, as well as the opportunity to obtain the target compounds a wide range of azoles with adamantly radical with a large enough output.

The technical result is achieved in a new method of obtaining adamant-1-illiteracy azoles of the General formula

.,,,

,,,

which consists in joining the adamantane derivative of the corresponding azole, and as adamantane derivative use 1,3-dehydroalanine, and as azole - 2-Mei, 3(5)-methylpyrazole and 4-methylpyrazole, 3,4-dinitrophenol, 1,2,4-triazole, 3-methylthiazole and 3-nitro-1,2,4-triazole, 5-methyltetra is l, and the process is carried out at a molar ratio of 1,3-dehydroalanine and Azola equal to 1:1, in the environment of diethyl ether at a temperature of 100°C for 4-5 hours.

The essence of the method shown in example joining 1,3-dehydroalanine 2-methylimidazole:

The reaction of 1,3-dehydroalanine with N-unsubstituted azoles flows mainly in the NH due azoles. The presence of additional nitrogen atoms has a great influence on the properties of the cyclic system. They enrich the system of free electron pairs and determine the preferred direction of attack for protons and other electrophiles. Additional nitrogen atoms also contribute to the lowering of the energy levels π - orbitals, resulting electrophilic attack on the carbon atoms in these molecules is difficult. The effect of additional nitrogen atoms may also be influenced by acidic and basic properties of heterocycles. On the one hand, the free pair of electrons of nitrogen atoms determine the direction of protonation, and most of azoles manifests itself as a stronger base than pyrrole. On the other hand, azolyl-anions are more stable than pyrrolyl-anion, so the azoles containing NH group, a stronger acid than pyrrole. So, for 2-methylimidazole value PKand=14, 3-methylpyrazole PKand =3,27, 3,4-dinitrophenol PKand=-2. The imidazole is the basis of the average force, other azoles - weak base; power grounds usually decreases with increasing number of nitrogen atoms in the molecule due to the inductive electron-withdrawing effect of additional nitrogen atoms. One consequence of the increased mobility of the protons of the N-unsubstituted azoles can be called easy formation of hydrogen bonds in liquid and solid phases, as well as a much greater solubility in water. Another important consequence of NH-acidity is that tautomeric forms of the N-unsubstituted Diatlov, triazoles and tetrazoles exist in the form of associates due to intermolecular proton transfer. The high nucleophilicity of 1,3-dehydroalanine allows you to get the products attach data of azoles with high yields in a fairly mild conditions in one stage.

The output is also influenced by the nature of asola. When adamantylamine of imidazoles, tetrazolo output is ˜90%if the reaction take nitro-derivatives of azoles, exit ˜70%.

The advantages of this method is the high product yield (70-90%), as well as the possibility of obtaining almost any homologues of this series, which are also intermediates for the synthesis of biologically active substances.

As shown by research, the Oia, the selectivity of the reaction is sensitive to temperature. Found that the maximum yield is achieved at a temperature of 100°C. Further increase in temperature and decrease in temperature leads to a decrease of the yield of the target products.

The use of diethyl ether as the medium also allows you to use it as a solvent for 1,3-dehydroalanine.

Changing the molar ratio of the reagents 1,3-DCA:azole to 1:1 reduces the obtaining by-products.

The increased duration of the reaction in the time interval of 4-5 hours, ceteris paribus, also leads to a slight increase output. Further increase in the duration of the reaction does not significantly change the yield of the target product. When reducing the length of the reaction less than 4 hours is not reached full conversion of the reactants.

The method is as follows.

To 1,3-dehydroalanine poured the solution Azola in diethyl ether in the ratio 1:1. The mixture is heated until complete evaporation of the ether, then the temperature is brought to 100°C and maintained at this temperature for 4-5 hours.

The invention is illustrated by the following examples:

Example 1.

Synthesis of N-(substituted)-2-methylimidazole.

To 5 g (0,037 mol) of 1,3-dehydroalanine in 30 ml of diethyl ether at is more of the solution 3,034 g (0,037 mol) of 2-methylimidazole in 20 ml of diethyl ether. The mixture is heated until complete evaporation of the ether and the temperature is brought to 100°C. At this temperature, allowed to stand 5 hours. The residue is crystallized from ethanol. Output 7,15 g (89.3 per cent).

Mass spectrum, m/z: 216 (M+, 100%). 201 ([M-CH3]+, 10%), 175 ([M-(CH3-HCN)]+, 7%), 159 ([M-C4H9]+, 50%), 135 (Ad+, 88%).

Example 2.

Synthesis of N-(substituted)-3(5)-methylpyrazole.

To 5 g (0,037 mol) of 1,3-dehydroalanine in 30 ml of diethyl ether is poured a solution of 3.03 g (0,037 mol) 3(5)-methylpyrazole in 20 ml of diethyl ether. The mixture is heated until complete evaporation of the ether and the temperature is brought to 100°C. At this temperature, incubated for 4.5 hours. The residue is crystallized from isopropanol. Output 7,26 g (90.2 per cent).

Mass spectrum, m/z: 216(M+, 53,4%), 135(Ad+, 100%), 81(PYR+, 9.9 per cent).

Example 3.

Synthesis of N-(substituted)-4-methylpyrazole.

To 5 g (0,037 mol) of 1,3-dehydroalanine in 30 ml of diethyl ether is poured a solution of 3.03 g (0,037 mol) of 4-methylpyrazole in 20 ml of diethyl ether. The mixture is heated until complete evaporation of the ether and the temperature is brought to 100°C. At this temperature, allowed to stand 5 hours. The residue is crystallized from isopropanol. Yield 7.2 g (89.5 per cent).

NMR1N spectrum (200 MHz, DMSO-D6): with a 1.75 (12H,Ad), 2,05 d (3H, CH3), of 2.15 (3H, Ad), 7,2 (1H, PYR), and 7.5 (1H, PYR).

Mass spectrum, m/z 216 (M +, 100%), 135 (Ad+, 98%), 81 ([M-Ad]+, 43,6%).

Example 4.

Synthesis of N-(substituted}-3,4-dinitrophenol

To 3,375 g (0,025 mol) of 1,3-dehydroalanine in 20 ml of diethyl ether is poured a solution of 4 g (0,025 mol) of 3,4-dinitrophenol in 30 ml of diethyl ether. The mixture is heated until complete evaporation of the ether and the temperature is brought to 100°C. At this temperature, allowed to stand 5 hours. The residue is crystallized from isopropanol. Output 5,13 g (70.3 per cent). The resulting product is a white crystalline substance with tPL=141-143°C.

Mass spectrum, m/z: 292 (M+, 18,8%), 275 ([M-Oh]+, 15,2%), 245 ([M-C4H9]+12%), 158 ([M-Ad]+that 2.8%), 135 (Ad+, 100%).

Example 5.

Synthesis of N-(substituted)-1,2,4-triazole.

To 2.7 g (0.02 mol) of 1,3-dehydroalanine in 20 ml of diethyl ether is poured a solution of 1.38 g (0.02 mol) of 1,2,4-triazole in 30 ml of diethyl ether. The mixture is heated until complete evaporation of the ether and the temperature is brought to 100°C. At this temperature, incubated for 4.5 hours. The residue is crystallized from heptane. The output of 3.65 g (89,8%).

Range PMR (Cl3), δppm: 1,67 (N, Ad), to 2.29 (3H, Ad), 7,60 (1H, TRY), 8,1 c (1H, TRY).

Example 6.

Synthesis of N-(substituted)-3-methyl-1,2,4-triazole.

To 4,73 g (0.035 mol) of 1,3-dehydroalanine in 30 ml of diethyl ether is poured the solution of 3.96 g (0.035 mol) of 3-methyl-1,2,4-triazole in 20 ml of diethyl ether. The mixture is heated until complete evaporation of the ether and the temperature is brought to 100°C. At this temperature, allowed to stand 5 hours. The residue is crystallized from isopropanol. Output 6,74 g (88.7 per cent).

NMR1N range: 1,68 (N, Ad), 2,18 d (3H, Ad), 2.9 (3H, CH3), and 7.7 (1H, TRY).

Example 7.

Synthesis of N-(substituted)-3-nitro-1,2,4-triazole.

To 4,73 g (0.035 mol) of 1,3-dehydroalanine in 30 ml of diethyl ether is poured a solution of 3.96 g (0.035 mol) of 3-nitro-1,2,4-triazole in 20 ml of diethyl ether. The mixture is heated until complete evaporation of the ether and the temperature is brought to 100°C. At this temperature, allowed to stand 5 hours. The residue is crystallized from isopropanol. Yield 6.2 g (71,5%). NMR1N spectrum (200 MHz, Cl3), δ, ppm: 1,78 (12H, Ad), 2,30 c (3H, Ad), 2,30 (1H, TRY).

Mass spectrum, m/z: 248 (M+, 29%), 191 ([M-C4H9]+2,4%), 149 ([AdN+], a 4.9%), 135 (Ad+, 100%).

Example 8.

Synthesis of 1-substituted-5-methyltetrazole.

To 6,75 g (0.05 mol) of 1,3-dehydroalanine in 30 ml of diethyl ether is poured a solution of 4.2 g (0.05 mol) of 5-methyltetrazole in 30 ml of diethyl ether. The mixture is heated until complete evaporation of the ether and the temperature is brought to 100°C. At this temperature, incubated for 4.5 hours. The residue is crystallized from heptane. Output 9,74 g (89,8%).

The resulting product is a white crystalline is emesto with t PL=115-116°C.

Range PMR (Cl3), δ, ppm: 1.8 W (6N, Ad), 2,35 (N, Ad), 2.75 (3H, CH3).

Conclusions.

Developed technologically versatile, melastatin method of synthesis adamantylidene azoles proceeding with a high yield of the target product. The structure of the described compounds is confirmed by PMR, NMR1N and mass spectra.

The method of obtaining adamant-1-alsogaray azoles of the General formula

,,,,

,,,

which consists in joining the adamantane derivative of the corresponding azole, characterized in that as adamantane derivative use 1,3-dehydroalanine, and as ASALA 2-Mei, 3(5)-methylpyrazole and 4-methylpyrazole, 3,4-dinitrophenol, 1,2,4-triazole, 3-methylthiazole and 3-nitro-1,2,4-triazole, 5-methyltetrazole, and the process is carried out at a molar ratio of 1,3-dehydroalanine and Azola equal to 1:1, in the environment of diethyl ether, at a temperature of 100°With, for 4-5 hours



 

Same patents:

The invention relates to new derivatives of aryl - and heteroarylboronic General formula I, where R1denotes a substituted phenyl or pyridyl, R2denotes a substituted phenyl, R3denotes hydrogen, (lower)alkyl, cyano, carboxy, esterified carboxylate, phenyl, 1H-tetrazolyl or the group,- CONR5R6, R5denotes hydrogen or the radical R7, R6represents -(CH2)mR7or R5and R6together with the nitrogen atom to which they are attached, denote morpholino, 2,6-dimethylmorpholine, piperidino, 4-(lower)alkylpiperazine, 4-(lower)alkoxyimino, 4-(lower)alkoxycarbonylmethyl or 4 formylpiperazine,7denotes phenyl, substituted phenyl, pyridyl, 1H-tetrazolyl, (lower)alkyl, cyano(lower)alkyl, hydroxy(lower)alkyl, di(lower)alkylamino(lower)alkyl, carboxy(lower)alkyl, (lower)alkoxycarbonyl(lower)alkyl, (lower)alkoxycarbonyl(lower)alkyl or phenyl(lower)alkoxycarbonyl, Radenotes hydrogen or hydroxy, Rbrepresents hydrogen, Z represents hydroxy or the group-OR8or-OC(O)NR8, R8denotes pyridyl or pyrimidinyl, X represents nitrogen or CH, m is 0, 1 or 2, n is 0, 1 or 2, and

The invention relates to new derivatives of formula (I), where R1- R4- hydrogen atoms; X - alkylene with 1 to 6 carbon atoms; Y is lower alkyl; B is - NR5R11where R5is a hydrogen atom, R11selected from 5 - to 6-membered heterocyclic radical, in which one ring member is a carbon and 1 to 4 members of the heteroatoms nitrogen, or sulfur, or their pharmaceutically acceptable salts, are useful as inhibitors of the synthesis of nitric oxide

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention describes a method for preparing 5-amino-3-sulfonylamino-1,2,4-triazoles of the formula (I): wherein R represents phenyl, para-methoxyphenyl, 2-naphthyl, para-para-toluene or para-chlorophenyl radical that can be used in manufacturing herbicides and antibacterial preparations. Method for preparing compounds of the formula (I) involves mixing 1-acetyl-3,5-diamino-1,2,4-triazole (II), pyridine and sulfonyl chloride of the formula (III): taken in the mole ratio = (II) : (III) = 1:((0.9-1.1), and prepared mixture is heated at stirring and temperature 80-120°C followed by dilution with water, and precipitated deposit is dissolved in alkaline metal hydroxide solution at heating at temperature 90-100°C and neutralized to pH value 6-8. Method provides reducing the cost of compounds of the formula (I) based on using the less expensive raw, decreasing duration of the process and enhancing its safety.

EFFECT: improved preparing method.

2 cl, 5 ex

FIELD: organic chemistry, medicine, biochemistry, pharmacy.

SUBSTANCE: invention describes derivatives of substituted triazoldiamine of the formula (I): wherein R1 represents (C1-C4)-alkyl, phenyl possibly substituted with halogen atom, amino-group substituted with -SO2-(C1-C4)-alkyl, imidazolyl, 1,2,4-triazolyl, imidazolidinone, dioxidoisothiazolidinyl, (C1-C4)-alkylpiperazinyl, residue -SO2- substituted with amino-group, (C1-C4)-alkylamino-group, (C1-C4)-dialkylamino-group, pyridinylamino-group, piperidinyl, hydroxyl or (C1-C4)-dialkylamino-(C1-C3)-alkylamino-group; R2 represents hydrogen atom (H); or R1 represents H and R2 means phenyl possibly substituted with halogen atom or -SO2-NH2; X represents -C(O)-, -C(S)- or -SO2-;R3 represents phenyl optionally substituted with 1-3 substitutes comprising halogen atom and nitro-group or 1-2 substitutes comprising (C1-C4)-alkoxy-group, hydroxy-(C1-C4)-alkyl, amino-group or (C1-C4)-alkyl possibly substituted with 1-3 halogen atoms by terminal carbon atom; (C3-C7)-cycloalkyl possibly substituted with 1-2 groups of (C1-C4)-alkyl; thienyl possibly substituted with halogen atom, (C1-C4)-alkyl that is substituted possibly with -CO2-(C1-C4)-alkyl, (C2-C4)-alkenyl that is substituted possibly with -CO2-(C1-C4)-alkyl, (C1-C4)-alkoxy-group, pyrrolyl, pyridinyl or amino-group substituted with -C(O)-C1-C4)-alkyl; (C1-C4)-alkyl substituted with thienyl or phenyl substituted with halogen atom; (C2-C8)-alkynyl substituted with phenyl; amino-group substituted with halogen-substituted phenyl; furyl, isoxazolyl, pyridinyl, dehydrobenzothienyl, thiazolyl or thiadiazolyl wherein thiazolyl and thiadiazolyl are substituted possibly with (C1-C4)-alkyl; to their pharmaceutically acceptable salts, a pharmaceutical composition based on thereof and a method for its preparing. New compounds possess selective inhibitory effect on activity of cyclin-dependent kinases and can be used in treatment of tumor diseases.

EFFECT: improved preparing method, valuable medicinal and biochemical properties of compounds and composition.

16 cl, 3 tbl, 26 ex

FIELD: organic chemistry, in particular production of biologically active compounds, pigments, and photographic materials.

SUBSTANCE: claimed method includes mixing of correspondent acid with aliphatic alcohol, addition of thionyl chloride and boiling of reaction mixture.

EFFECT: decreased alcohol consumption, its reusing without pre-drying; accelerated synthesis method without byproduct formation.

9 ex

The invention relates to novel triazole compounds of the General formula (1), where a denotes a linear or branched C1-C18-alkylenes group which may comprise at least one group which is selected from O, S, CONH, COO,3-C6-cycloalkene or double or triple bond; In denotes the radical of formula (a), (b) or (C); R1denotes H, NH2WITH3-C6-cycloalkyl or1-C8-alkyl, which is not substituted or substituted OS1-C8-alkyl; R2denotes H, HE, C1-C8-alkyl, C3-6-cycloalkyl, CF3, CN, NR3R4, SR3or CO2R3where R3denotes N or C1-C8-alkyl, a R4denotes H, C1-C8-alkyl, or COR3where R3stands WITH1-C8-alkyl; Ar represents naphthyl, phenyl with 1-2 substituent selected from C1-C8-alkyl, CF3, CHF2, NO2, SR3, SO2R3where R3means1-C8-alkyl; and pyridyl, pyrimidyl or triazinyl, which have from 1 to 3 substituents selected from C1-C8-alkyl, C2-C6-alkenyl, C2-C6-quinil, halogen, CN, CF3, OR4where R43-C6-lalouche possibly condensed, phenylalkylamine or 5-membered aromatic heterocycle with 1 to 2 nitrogen atoms, which may be condensed with a benzene ring
The invention relates to the field of production of organic substances and can be used in the manufacture of medicinal and biological active compounds, dyes and photographic materials

The invention relates to new chemical compounds having valuable properties, in particular to new derivatives of sulfonamidophenylhydrazine

FIELD: organic chemistry, chemical technology, medicine.

SUBSTANCE: invention relates to water-soluble azole compounds that can be used in biology and medicine. Invention describes a water-soluble azole compound of the formula (I):

or its pharmaceutically acceptable salt wherein each R and R1 means independently hydrogen atom or (C1-C6)-alkyl; A means group of the formula:

wherein R3 represents phenyl group with one or more halide atoms as substitutes; R4 represents hydrogen atom or -CH3; R5 represents hydrogen atom or in common with R4 it can represent =CH2; R6 represents 5- or 6-membered nitrogen-containing cycle that can comprise if necessary as substituted one or more groups taken among halogen atom, =O group, phenyl substituted with one or more groups taken among -CN, -(C6H4)-OCH2-CF2-CHF2 and -CH=CH-(C6H4)-OCH2-CF2-CHF2 or phenyl substituted with one or more groups taken among halogen atom and methylpyrazolyl group. Also, invention describes a method for preparing a water-soluble azole compound. Invention provides preparing new compounds that can be useful in medicine.

EFFECT: improved preparing method, valuable medicinal properties of compounds.

4 ex

FIELD: organic chemistry, chemical technology, pharmacy.

SUBSTANCE: invention describes a method for synthesis of fluconazole monohydrate of the formula (I): . Method involves hydrolysis of silyl ester derivative of the formula (II): wherein R2 means hydrogen atom, (C1-C10)-alkyl or phenyl group; R3 and R4 mean independently of one another (C1-C10)-alkyl or phenyl group at pH value below 3 or above 8 in an aqueous solution followed by cooling the prepared reaction mixture and isolation of the precipitated fluconazole monohydrate. Also, invention describes methods for synthesis of crystalline modification II of fluconazole of the formula (I). These methods involve dissolving anhydrous fluconazole or its monohydrate in (C1-C4)-alcohol of the linear or branched chain at the boiling point and cooling this solution at the rate 5-15°C/h, or fluconazole monohydrate is dried at 30-70°C. Except for, invention describes a method for synthesis of crystalline modification I of fluconazole of the formula (I) wherein fluconazole monohydrate is dried at 80°C. This invention provides preparing pure or easily purifying fluconazole in crystalline modifications allowing easy preparing the suitable medicinal formulations from them.

EFFECT: improved synthesis method.

16 cl, 1 tbl, 7 dwg, 8 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention describes the improved method for preparing 1-(4-chlorophenyl)-3-(1,2,4-triazol-1-yl-methyl)-4,4-dimethylpentane-3-ol. Method involves interaction of 1,2,4-triazole with 2-(4-chlorophenylethyl)-2-tert.-butyloxirane in the presence of potassium hydroxide in n-butanol medium. Process is carried out in reaction mixture directly containing 2-(4-chlorophenylethyl)-2-tert.-butyloxirane prepared by interaction of 4,4-dimethyl-1-(4-chlorophenyl)-pentane-3-one with trimethylsulfonium methylsulfate in n-butanol medium at 50-55°C without preliminary isolation of oxirane and its purification. Method provides reducing number of operations, time for carrying out the process and to retain high yield of product.

EFFECT: improved method for preparing.

4 cl, 3 ex

FIELD: new lubricant oiliness addend.

SUBSTANCE: claimed method includes reaction of equimolar amounts of 1-(N,N-dimethylaminomethyl)-1,2,4-triazol and O-(n-butyl)-O-(2-ethyl-n-hexyl)-dithiophosphoric acid at 80-100°C in toluene medium for 2-4 h to produce target product with yield of 94-100 %.

EFFECT: addend compatible with base oil with improved antiscoring properties.

1 cl, 1 ex, 2 tbl

FIELD: synthesis of lubricant oil additives.

SUBSTANCE: method for production of O-(2-ethyl-n-hexil)-O-3,4,5-trithiatricyclo[5.2.1.02,6]-dez-8-yl-methyl)-dithiophosphoric acid 1-(N,N-dimethylaminomethyl)-1,2,4-triazole salt of general formula

is disclosed. 1-(N,N-dimethylaminomethyl)-1,2,4-triazole is brought into reaction with equimolar amount of O-(2-ethyl-n-hexyl)-O-3,4,5-trithiatricyclo[5.2.1.02,6]-dez-8-yl-methyl)-dithiophosphoric acid in toluene medium at 80-100°C for 2-4 h.

EFFECT: ash-free antiscoring lubricant oil additive operating under high pressure.

2 tbl, 1 ex

FIELD: synthesis of lubricant oil additives.

SUBSTANCE: method for production of O-(n-butyl)-O-3,4,5-trithiatricyclo-dez-8-yl-methyl)-dithiophosphoric acid 1-(N,N-dimethylaminomethyl)-1,2,4-triazole salt of general formula

is disclosed. 1-(N,N-dimethylaminomethyl)-1,2,4-triazole is brought into reaction with equimolar amount of O-(n-butyl)-O-3,4,5-trithiatricyclo-dez-8-yl-methyl)-dithiophosphoric acid in toluene medium at 80-100°C for 2-4 h.

EFFECT: ash-free antiscoring lubricant oil additive operating under high pressure.

2 tbl, 1 ex

FIELD: organic chemistry, pharmaceutical compositions.

SUBSTANCE: 5-aryl-1H-1,2,4-triazole derivatives of general formula I

, pharmaceutically acceptable salts thereof or pharmaceutical composition containing the same are described. In formula R1 is C1-C6-alkyl, C1-C6-haloalkyl or phenyl; R2 is C3-C8-cycloalkyl; phenyl optionally substituted with one or more substituents selected from C1-C4-alkyl; halogen, hydroxyl, C1-C4-alkoxy, nitro, di-(C1-C4)-alkylamino, C1-C4-alkylsulphonyl, C1-C4- alkylsulphonylamino, and methylenedioxy; phenyl-(C1-C4)-alkyl, wherein phenyl is substituted with C1-C4-alkoxy; or pyridil. New compounds are effective and selective cyclooxygenase-2 (COX-2) inhibitors and useful in treatment of inflammations.

EFFECT: new compounds for inflammation treatment.

10 cl, 36 ex, 1 tbl

The invention relates to the chemistry of heterocyclic compounds, namely to substituted 1-(pyridinyl-3)-2-azolylmethyl General formula I

where R means a hydrogen atom, an unbranched or branched alkyl with a number of carbon atoms of from one to eight, cycloalkyl with the number of carbon atoms from three to eight, cycloalkenyl with the total number of atoms from four to ten, alkylsilanes with the total number of atoms from four to ten, X denotes a nitrogen atom or CH group, which possess fungicidal activity and can be used as agricultural, industrial, medical or veterinary fungicides

The invention relates to substituted 3,5-diphenyl-1,2,4-triazole and their use as pharmaceutical agents, which form chelate complexes with metal
Up!