Derivatives of 4-oxo-3h-phthalazine-1-acetic acid, a method of obtaining derivatives complex alilovic esters of 4-oxo-3h - phthalazine-1-acetic acid

 

(57) Abstract:

Use: in organic chemistry. The inventive product - derivatives of 4-oxo-3H-talonen-1-acetic acid of formula I, where R1- C1-C6-alkyl - intermediate compounds. The products of formula II, where R1- C1-C6-alkyl; R2and R3the same or different and represent a hydrogen atom, fluorine, chlortrimeton. Reagent 1 according to formula III, where W is the group CN or - C(S)NH2. The reagent 2 in the formula IV. Reaction conditions: hydrogen sulfide, tertiary amine. 2 S. p. f - crystals. The structure of formulas I, II (see Fig.) III (R2, R3)C6H2-NO2-Cl (IV).

The invention relates to the field exitlinks acids, in particular to the intermediate compounds - derivatives of 1-oxo-3H-phthalazine-1-acetic acid of General formula

< / BR>
(A) where R1-C1-C6-alkyl, and the method of obtaining derivatives complex alilovic esters of 4-oxo-3H-phthalazine-1-acetic acid of General formula

< / BR>
(I) where R1-C1-C6-alkyl, R2and R3may be the same or different and represent a hydrogen atom, chlorine or trifluoromethyl, which are inhibitors oldselected.

The known method sing acid and ortho-nitroanilide. However, the disadvantage of this method is the complexity of the process by conducting the process in four stages.

The aim of the invention is to create new and derivative acceptlicense acid, simplifying the process.

This goal is achieved by the proposed compounds of formula a and the proposed method of obtaining compounds of formula 1 with the use of derivatives acceptlicense acid and ortho-nitrophenylamino, the distinguishing feature of which is the fact that the compound of General formula

< / BR>
(II) where R1have the above meanings;

W is cyano or the group-CH2, is subjected to the interaction with the compound of General formula

< / BR>
(III) where R2and R3have the above meanings, in the presence of hydrogen sulfide, and in the case when W is cyano, in the presence of a tertiary amine.

The compound of formula II is subjected to interaction with the compound of the formula III in order to obtain the compounds of formula I. generally, the reaction is carried out in a polar solvent. Suitable solvents include sulfolane the tetrahydrothiophene-1,1-dioxide, pyridine, dialkyl ethers of diethylene glycol (for example, diethyl ether of diethylene glycol) is round, basically, ranges from about 110-180aboutWith, and preferred is a temperature distillation of the solvent. The reaction pressure is not critical. Basically, the pressure of the reaction is in the range of about from 0.5 to 2 ATM, and preferred is the ambient pressure (i.e. a pressure equal to 1 ATM). If W is a JV, the compound of formula II is reacted with a compound of formula III in the presence of a tertiary amine. Suitable tertiary amines are three (C2-C6-bonds alkylamines, for example triethylamine.

The compound of formula II, where W is cyano, can be obtained through a reaction between the compounds of formula IIA with a compound of formula L-CH2CN, where L is chlorine, bromine, -OSO2(C1-C4)-alkyl), or-SO2-aryl, where aryl is phenyl or naphthyl, optionally substituted C1-C4-alkyl, halogen or nitro, in the presence of a base. Examples of suitable bases can serve as an alkali metal hydride such as sodium hydride, carbonates of alkali metals such as potassium carbonate; hydroxides of alkali metals such as sodium hydroxide or potassium, and the alkaline alkoxides IU the which is inert under the reaction conditions. Suitable solvents are inert solvents, such as dimethylformamide, dimethylacetamide, acetone, and diglyme. The reaction is mostly carried out at a temperature from 0 to 100aboutC. Preferably, if the reaction temperature is about 40 to 60aboutC.

The compound of formula II, where W is-C(S)NH2can be obtained by reaction of compounds of formula IIB, where W is a JV with hydrogen sulfide in the presence of a tertiary amine, such as tri(C2-C6-alkylamine(e.g., triethylamine) and in the presence of a solvent such as pyridine or dimethylformamide. The preferred solvent is dimethylformamide. In General, the reaction proceeds at a temperature of from room temperature to about 100aboutC. the Preferred reaction temperature is about 40 to 60aboutC.

P R I m e R 1. Ethyl-3-diacetamido-4-acceptilation-1-ylacetic.

Through a solution of ethyl-3-cyanomethyl-4-acceptilation-1-ilaclama (54,2 g) in dimethylformamide (200 ml) containing triethylamine (1 ml) maintained at 60aboutWith, barbotirovany hydrogen sulfide. After 15 min bubbling of hydrogen sulfide was stopped, and the heating was continued for 2 hours Then the solution was cooled to washed with water (2 x 200 ml), and then dried by air, resulting in a received target connection output (57,8 g; so pl. 149-151aboutC).

P R I m m e R 2. Ethyl-3-(5-triftormetilfosfinov-2-ylmethyl)-4-oxo-3H-phthalazine-1-ylacetic.

Procedure A. a Solution of ethyl-3-cyanomethyl-4-oxoproline-1-ylacetic (10,84 g) and a catalytic amount of triethylamine (0.2 g) in dimethylformamide (40 ml) maintained at 50-55aboutWith, boiled with hydrogen sulfide for 15 minutes After stopping the boiling point of the hydrogen sulfide reaction was continued for 3 hours At this stage, the solution of consisely hydrogen sulfide, after which the reaction mixture was added 4-chloro-3-nitrobenzotrifluoride (for 9.47 g). The reaction mixture immediately turned a pale orange color and then it was heated to 150aboutC for 2.5 h Then the solution was cooled to room temperature and one drop was added to a mixture of ice water and ethanol (800 ml, 4:1), pH of the aqueous ethanol was brought to approximately 2.0 with the help of a few drops of 6 N. hydrochloric acid. The obtained granular solid was filtered, and the residue was led from ethanol-methylene chloride (50 ml, 3:1). The solid is collected by filtration and dried with air, resulting in the obtained target compound (yield tion.

Procedure C. To a solution of ethyl-3-diacetamido-4-acceptilation-1-ilaclama (6,1 g) and dimethylformamide (30 ml), saturated with hydrogen sulfide was added 4-chloro-3-nitrobenzotrifluoride (4.5 g) and the resulting solution was slowly heated to a temperature of distillation. When this temperature was reached, through the solution slowly let in a stream of hydrogen sulfide and within 4 h continued reflux. Then the reaction mixture was cooled and poured into ice water (500 ml). The resulting kamadi was separated by decantation, after which it was pereirae with ethanol (75 ml). Granular light yellow solid substance was filtered, the precipitate was collected, then was led from ethanol (200 ml) and received the target compound (yield 4.1 g).

In a similar way received ethyl-3-(7-chlorobenzothiazole-2-ylmethyl)-4-oxo-3-phthalazine-1-ylacetic, (so pl. 119aboutC) and ethyl-3-(5-chloro-7-foroperational-2-ylmethyl)-4-oxo-3-N-phthalazine-1-yl-acetate, (so pl. 202-204aboutC) using 2,3-dichloronitrobenzene and 2.5-sodium dichloro-3-pteronotropis respectively, instead of 4-chloro-3-nitrobenzotrifluoride.

P R I m e R 3. 1. Methyl 1H-indazol-3-ylacetic.

A solution of 1H-indazol-3-acetic acid (1.0 g) in methanol (30 ml), steriade the promo mixture was concentrated to low volume and diluted with ethyl acetate (20 ml). The organic layer was washed with water (2x10 ml), and then a solution of bicabonate sodium (10 ml, 10%). Then the ethyl acetate layer was collected, dried, and received the target connection (so pl. 146aboutC).

II. Methyl-(I-cyanomethyl)-1-N-indazol-3-ylacetic.

To a solution of methyl-1-N-indazol-3-ilaclama (1.9 g) in dimethyl-formamide (4 ml) was added sodium hydrate (0,58 g, 50% dispersion in oil), after which the mixture was stirred for 15 min at room temperature. Then add chloroacetonitrile (1.9 g) dissolved in dimethylformamide (2 ml) and the resulting mixture was stirred for another 6 hours Then the mixture was poured into ice water (20 ml), the pH was brought to 3 by adding sufficient dilute Hcl and the resulting precipitate was collected and dried (yield of 1.87 g, so pl. 128-134aboutC).

P R I m e R 4. 3-(7-Chlorobenzothiazole-2-ylmethyl)-4-oxo-3-N-phthalazine-1-yl-vinegar-Naya acid.

To a solution of ethyl-3-(7-chlorobenzothiazole-2-ylmethyl)4-oxo-3-N-phthalazine-1 - ilaclama (800 mg) in a mixture of ethanol in tetrahydrofuran (30 ml, 2:1) was added 5 ml of 1% aqueous potassium hydroxide solution, after which the mixture was stirred at room temperature for 2 hours, the Reaction mixture was concentrated by evaporation under vacuum, and received the Noi Hcl was obtained a white precipitate. This precipitate was collected by filtration, air dried, and then were led out of methylene chloride (10 ml) and received the target connection, exit 273 mg; so pl. 168aboutC.

Similarly, ethyl-3-(5-chloro-7-chlorobenzothiazole-2-ylmethyl)- 4-oxo-3-N-Palatinate hydrolyzed with the formation of 3-(5-chloro-7-fermentation-2-ylmethyl)-4-oxo-3-N-phthalazine-1 - yl-acetic acid. (So pl. 207-207,5aboutC).

P R I m e R 5. 1,4-Oxo-pyrido-[3,2-c] and 3-occupied-[2,3-C]-furan-1-ylideneamino acid tert-butyl ether.

A mixture of commercially available 2,3-pyridylcarbinol anhydride (29,8) of tert-butoxycarbonylmethylene (75.2 g) and methylene chloride (1000 ml) was stirred at room temperature for 60 h the mixture is Then evaporated to dryness and the residue was chromatographically on silica gel (2.0 kg). After careful serirovani solution of methylene chloride and ethyl acetate (49:1) and dispensing luttich fractions using thin-layer chromatography was allocated two products. The less polar product, signs And was identified as a mixture (1:1) E or Z 3-occupied-[2,3-C]-furan-1 - or-den-acetic acid t-butyl ester H NMR (DCL3, 25 MHz), and 1.5 (s, N); 6,1 (s, 1H); 7,8 (DD. J=6 Hz, 1H); 8,40 (DD. J=6 Hz, J=1 Hz, 1H); 9,1 (DD. JUB>, 250 MHz) 1,5 (, N); 6,2 (s, 1H; 7,9) (DD, J=6 Hz, 1H); 9,0 (DD. J=6 Hz, 1H); 9,2 (DD. J=12 Hz, 1H).

The more polar product, denoted by, was identified as a mixture (about 1: 10) E 3-oxo-pyrido-[3,2-C] -furan-1-ilidene acetic acid tert-butyl ester and (E or Z 3-oxopyridine-[2,3-C]-furan-1-ylideneamino acid tert-butyl ether complex. The less polar product was not isolated in pure components. The more polar product was again chromatographically on silica gel (500 g) and buriable solution of methylene chloride in ethyl acetate (9:1). In the evaporation of the early fractions received net E 3-oxo-pyrido-[3,2-C]-furan - 1-ilidene acetic acid tert-butyl ester (1.8 g; so pl. 113-114aboutC). After viperine late fractions were obtained pure E or Z 3-oxo-pyrido-[2,3-C]-furan-1-ilidene-acetic acid tert-butyl ester (11.5 g; so pl. 118aboutC).

II. tert-Butyl 8-oxo-7H-pyrido-[2,3-C]-pyridazin-5-ylacetic.

To a solution of E 3-oxo-pyrido-[3,2-C] -furan-1-ilidene-acetic acid tert-butyl ether complex (1,85) in ethanol (10 ml) was carefully added hydrazine hydrate (1.3 ml) and the resulting mixture was gently heated under reflux for 1 h Then the solution was concentrated to remove ataia pH to 2.0. The solid precipitate was collected and dried air (1,36 g; so pl. 186-188aboutC).

P R I m e R 6. I. tert-Butyl-5-oxo-6N-pyrido-[2,3-d]-pyridazin-8-ylacetic.

To a solution of E or Z 3-oxo-pyrido-[2,3-C]-furan-1-ilidene-acetic acid tert-butyl ether complex (so pl. 118aboutC); (10.0 g) in ethanol (25 ml) was added one drop of hydrazine hydrate (10 ml) and the resulting solution was heated in a flask under reflux for 10 minutes Then the solution is evaporated to remove the ethanol, the residue was diluted with water (20 ml) and was added sufficient 10% Hcl to bring the pH to 6. The precipitated solid was filtered, collected and dried air (8,9 g; so pl. 178-179aboutC).

II. tert-Butyl 6-(5-triftormetilfosfinov-2-ylmethyl)-5-oxo-6N-pyrido-2,3-pyridazin- -8-ylacetic.

To a solution of tert-butyl 5-oxo-6N-pyrido-[2,3-d]- pyridazin-8-yl-abeta (0.5 g) in dimethylformamide (5 ml) containing tert-piperonyl potassium (0.25 g) was added 5-trifluromethyl-2-chloromethylthiazole (0.55 g). The resulting solution was stirred at room temperature overnight and then was poured into ice water (20 ml), then added sufficient 10% Hcl to bring the pH of the solution to 5.0 and the obtained crude solid wasp, the resulting received target product (0.66 g; so pl. 121-122aboutC).

Thus, the proposed intermediate and the proposed method allows to obtain the compounds of formula I on simpler technology (one stage against the 4 stages in a known way).

1.Derivatives of 4-oxo-3H-phthalazine-1-acetic acid of General formula

< / BR>
where R1- C1- C6-alkyl.

2. The method of obtaining derivatives complex alilovic esters of 4-oxo-3H-phthalazine-1-acetic acid of General formula

< / BR>
where R1- C1- C6-alkyl,

R2and R3the same or different, is hydrogen, fluorine, chlorine or trifluoromethyl,

using derivatives acceptlicense acid and orthonitrophenol, characterized in that the compound of General formula

< / BR>
where R1has the specified values,

W is cyano or a group

C

subjected to interaction with the compound of General formula

< / BR>
where R2and R3have the specified values,

in the presence of hydrogen sulfide in the case when W is cyano, - in the presence of a tertiary amine.

 

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11 cl, 24 ex, 1 tbl

FIELD: chemistry.

SUBSTANCE: disclosed compounds can be used as a medicinal agent having CXCR2 inhibiting properties. In formula I , X denotes -CR3=CR4-, -CR5=N-, -N=CR6-, -NR7- or -S-; R3, R4, R5 and R6 independently denote hydrogen, F, CI, Br, I; R7 denotes hydrogen; Y1, Y2, Y3 and Y4 independently denote -CR8- or nitrogen, provided that at least two of Y1, Y2, Y3 and Y4 denote -CR8-; where R8 denotes hydrogen, F, CI, Br, I; A denotes a cycloalkyl having 3, 4, 5, 6, 7 or 8 carbon atoms; a bicyclic partially saturated 9-member cycloalkyl; a bicyclic partially saturated 9-10-member heterocycle in which two atoms in the ring are oxygen atoms; phenyl; naphthyl; a 5-6-member heteroaryl in which 1-3 atoms in the ring are oxygen, sulphur and nitrogen atoms; a 9-10-member bicyclic heteroaryl in which 1-3 atoms in the ring are nitrogen, oxygen and sulphur atoms; a 6-member heterocycle in which one atom in the ring is a nitrogen atom and which can be unsubstituted or substituted with alkyl having 1, 2, 3 or 4 carbon atoms, -C(O)CH3, -C(O)CH2CH3, -C(O)cyclopropyl, -C(O)CF3 and -C(O)OC(CH3)3; where phenyl, heterocyclic or heteroaryl radical is substituted with 1, 2 or 3 radicals selected from a group consisting of F, O, Br, I, OH, CN, NO2, SCF3, SF3, alkyl having 1, 2, 3, 4, 5 or 6 carbon atoms, where 1, 2, 3 hydrogen atoms may be substituted with fluorine atoms; cycloalkyl having 3, 4, 5 or 6 carbon atoms; alkoxy having 1, 2, 3, 4, 5 or 6 carbon atoms, where 1, 2, 3 hydrogen atoms may be substituted with fluorine atoms; -S-alkyl having 1, 2, 3, 4, 5 or 6 carbon atoms, where 1, 2, 3 hydrogen atoms may be substituted with fluorine atoms; -NR9R10, C(O)R44, S(O)SR47, -(CH2)k-phenyl, 5-6-member heteroaryl, in which 1-3 atoms in the ring are nitrogen and sulphur atoms; where the phenyl radical may be substituted with F, CI, Br, I; R9 is an alkyl having 1, 2, 3 or 4 carbon atoms; R10 is an alkyl having 1, 2, 3 or 4 carbon atoms; R44 is an alkyl having 1, 2, 3 or 4 carbon atoms, where 1, 2, 3 hydrogen atoms may be substituted with fluorine atoms; alkoxy having 1, 2, 3 or 4 carbon atoms, cycloalkyl having 3, 4, 5 or 6 carbon atoms; R47 is an alkyl having 1, 2, 3 or 4 carbon atoms; k equals 0, 1, 2 or 3; s equals 1 or 2; B is -O-C(R11R12), -C≡C-, -CR52=CR53-, -C(R13R14)C(R15R16), -NR17-C(R18R19); R11, R12, R13, R14, R15, R16, R17, R18, R19, R52, R53 independently denote hydrogen or alkyl having 1, 2, 3 or 4 carbon atoms; D is C(O)OH, C(O)NHR21 or C(=NR58)NHR22; R21 and R22 independently denote hydrogen, -SO2-alkyl having 1, 2, 3 or 4 carbon atoms, -SO2-phenyl; R58 is OH; R1 and R2 independently denote an alkyl having 1, 2, 3, 4, 5 or 6 carbon atoms, where the alkyl radicals are unsubstituted or substituted with 1 radical selected from a group consisting of F, Cl, Br, I, phenyl substituted with OH; or R1 and R2, taken together with a carbon atom with which they are bonded form a 3-, 4-, 5- or 6-member carbocycle. The invention also relates to use of formula I compounds in preparing a medicinal agent which has CXCR2 inhibiting properties, to a medicinal agent which containing an effective amount of the disclosed compound and having CXCR2 inhibiting properties, as well as to use of formula II compounds (formula and values of radicals are given in the formula of invention) in preparing a medicinal agent having CXCR2 inhibiting properties.

EFFECT: high effectiveness of application.

10 cl, 384 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a compound of formula

,

where R denotes a substituted or unsubstituted thiazolyl group of formula or ; R4 and R5, each independently, are selected from i) hydrogen; ii) a substituted or unsubstituted C1-C6 linear, C3-C6 branched or C3-C6 cyclic alkyl; iii) a substituted or unsubstituted phenyl; iv) a substituted or unsubstituted heteroaryl containing 5 or 6 ring atoms and 1 or 2 heteratoms, where the heteroatoms are selected from nitrogen, oxygen, sulphur and combination thereof; or R4 and R5 can be taken together to form a saturated or unsaturated ring, having 5-7 atoms; said substitutes are independently selected from one or more groups, selected from C1-C6 linear, C3-C6 branched or C3-C6 cyclic alkyl, halogen, hydroxyl or cyano; R6 denotes a group selected from i) hydrogen; ii) a substituted or unsubstituted C1-C6 linear, C3-C6 branched or C3-C6 cyclic alkyl; iii) a substituted or unsubstituted phenyl or iv) a substituted or unsubstituted heteroaryl containing 5 or 6 ring atoms and 1 or 2 heteroatoms, where the heteroatoms are selected from nitrogen, oxygen, sulphur and combination thereof; where said substitutes are independently selected from one or more groups selected from C1-C6 linear, C3-C6 branched or C3-C6 cyclic alkyl, halogen, hydroxyl or cyano; R1 is selected from i) hydrogen; ii) C1-C6 linear or C3-C6 branched alkyl; iii) a substituted or unsubstituted phenyl or iv) a substituted or unsubstituted benzyl; where said substitutes are independently selected from one or more groups selected from C1-C6 linear, C3-C6 branched or C3-C6 cyclic alkyl, halogen, hydroxyl or cyano; R2 is selected from i) C1-C6 linear or C3-C6 branched alkyl or ii) C1-C6 linear or C3-C6 branched alkoxy; R3 denotes hydrogen or C1-C4 linear or C3-C6 branched alkyl.

EFFECT: compounds of formula (I) are effective as human protein tyrosine phosphatase beta (HPTP-β) inhibitors.

20 cl, 10 tbl, 8 ex

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of general formula (I) , where is a substituted 5-member heteroaryl ring selected from thienyl, thiazolyl, oxazolyl, pyrrolyl, imidazolyl or pyrazolyl, W is selected from a group comprising N and -C=; M is selected from a group comprising -C(O)N(R1)OR2, -CXCONR1R2 and -C(O)OR1, or M is -C1-C2alkyl-C(O)N(R1)OR2, wherein is , R1 and R2 are independently selected from a group comprising -H, C1-C3-alkyl, C6-aryl, and C1-C3-alkyl-C6-aryl; R is selected from a group comprising H, C1-C3alkyl, halogen, NR1R2, -OR1 and C6aryl; n is an integer from 0 to 1; L and Y are as indicated in the claim; and to compounds of formula (II) , where L2 is selected from a group comprising H, - C0-C3alkyl- C6aryl, -C0-C3alkyl-heteroaryl, where the heteroaryl is pyridyl; -C1-C6alkyl, Y and M are the same as for compounds of formula (I). The invention also relates to a pharmaceutical composition based on compounds (I) and (II), having inhibiting action on histone deacetylase (HDAC), a method of inhibiting and a method of treating a disease which is sensitive to the HDAC inhibitor.

EFFECT: compounds of formula I and II as histone deacetylase inhibitors.

18 cl, 18 dwg, 10 tbl, 19 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention relates to novel compounds of formula III or to its pharmaceutically acceptable salts, in which: R1 and R2 are independently selected from group, consisting of: (a) H, (b) (C2-C6)alkyl, (c) C1-C6 alkyl, interrupted by one or more groups -O-, (d) (C0-C3)alkyl-(C3-C7)cycloalkyl and (e) (CH2)nQ, where n=1-2 and where Q stands for aromatic ring system, which has from 5 to 6 ring atoms C, and Q can be independently substituted with groups up to 3 in number, selected from halogen, on condition that R1 and R2 simultaneously do not stand for H, and each alkyl of R1 and R2 can be independently substituted with one or more groups, selected from group, consisting of halogen, hydroxy, cyano, CF3 or C1-C4 alkyl, or R1 and R2 together with carbon, to which they are attached, form 3-7-member cycloalkyl or 6-member heterocycloalkyl ring, including one oxygen atom and which in case of necessity carries C1-C4 alkyl substituent, or R1 and R2 together with carbon, to which they are connected, form 3-7-member cycloalkyl ring, substituted with R20 and R21, and R20 and R21 together with carbon or carbons, to which they are connected, form 3-7-member cycloalkyl ring; R6 stands for C1-C6 alkyl; each R7 independently stands for C1-C6 alkyl; Y stands for -O-; R4 is selected from group, consisting of: (a) (C0-C3)alkyl-(C3-C7)cycloalkyl, (b) trifluoroethyl, and (c) trifluoropropyl; Z stands for phenyl or bicyclic ring system, which has 9 ring atoms, independently selected from C, N, O and S, on condition that not more than 3 ring atoms in any single ring differs from C, and said ring system can carry to 3 substituents, independently selected from group, consisting of R6, CF3 and SR6; and R5 is selected from group, consisting of NO2, NH2, F, Cl, Br, CN, SR6, S(O)2N(R7)2 and (C1-C4)alkyl, and each alkyl can be independently substituted with one or more halogens or CF3. Invention also relates to pharmaceutical composition for treatment of neurodegenerative disorder or improvement of cognitive function, containing therapeutically effective quantity of said compound; as well as to method of treatment of neurodegenerative disorder, for instance Alzheimer's disease, or improvement of cognitive function.

EFFECT: compounds act as modulators of gamma-secretase.

31 cl, 14 tbl, 3147 ex, 1 dwg

FIELD: chemistry.

SUBSTANCE: invention relates to methods of producing thiophenols during reaction of corresponding disulphide with hydrogen in presence of a heterogeneous hydrogenation catalyst based on a transition metal. In particular, method of producing a compound of formula (I') involves reaction of a compound of formula (II'), wherein R is H or with H2 in presence of a heterogeneous hydrogenation catalyst based on a transition metal, where heterogeneous hydrogenation catalyst based on a transition metal is a Raney catalyst, Pd/C, Pd(OH)2/C, nanoparticles of palladium (0), micro-encapsulated in a polyurea matrix, Au/TiO2, Rh/C, Ru/Al2O3, Ir/CaCO3, Pt/C or mixture thereof. When reaction is carried out in presence of an acylating reagent, such as anhydride or halide of carboxylic acid, acylated thiophenol is obtained.

EFFECT: pharmaceutically active compound S-[2-[1-(2-ethylbutyl)cyclohexylcarbonylamino]-phenyl]-2-methylthiopropionate is obtained during said method.

20 cl, 16 ex, 1 tbl

FIELD: pharmacology.

SUBSTANCE: compounds of the invention are intended for manufacture of a pharmaceutical composition, kit or drug. The invention also relates to a process for preparation of compounds of the invention (versions). Compounds of the invention are intended for use in the prevention or treatment of diseases caused by RNA-containing viruses belonging to enteroviruses, metapneumoviruses or pneumoviruses.

EFFECT: amide compounds for treatment or prevention of diseases caused by RNA-containing viruses.

26 cl, 8 tbl, 5 ex

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