How sulfanilamide heterocyclic compounds, a method of obtaining a 4 - sulfinpyrazone and sulfinamide connection

 

(57) Abstract:

Describes how to sulfanilamide heterocyclic compounds, characterized in that the derivative of the formula RS(O)X in which R denotes a linear or branched alkyl group with 1 to 4 C-atoms, substituted by one or more, same or different halogen atoms, and X denotes a halogen atom, a hydroxyl group, or one of its salts, dialkylamino group NR2R3and R2and R3represents an alkyl or halogenoalkane group with 1 to 4 C-atoms; or aryloxy-group in which the aryl portion preferably corresponds to a phenyl group, if necessary substituted by one or more halogen atoms or alkyl or halogenoalkane groups with 1 to 4 C-atoms; enter into interaction with the heterocyclic compound Gets selected in the group comprising pyrrole, pyrazoles, imidazoles, oksazolov, isoxazoles, isothiazole, thiazole, triazole, all of these heterocycles Gets if necessary substituted by one or more atoms or groups selected from among halogen, amino, mono - or dialkylamino-, nitrile, aryl groups, aryl groups, substituted one or nasalcavity, that R is different from n-butyl, when Het represents pyrrole, and R is different from methyl, when Het denotes a 2,5-dimethylpyrrole. Also describes sulfinamide connection and method for producing 4-sulfinpyrazone. The technical result is to simplify the process without compromising the overall yield of the reaction. 3 S. and 13 C.p. f-crystals.

The present invention relates to a new method of sulfanilamide heterocyclic compounds. Sulfinpyrasone heterocyclic compounds, i.e., the introduction of the group RS(O)-, classically carried out by exposure of the product formula RSX (where R and X have the meanings stated below) on the heterocyclic compound containing a hydrogen atom from the substituted carbon. This reaction, therefore, leads to a sulfenyl-geterotsiklicheskikh connection that you want to oxidize to obtain the target sulfanilimide connection. However, it turns out that this oxidation step is often difficult. Moreover, the connection RSX in some cases found to be very toxic, for example, the connection CF3SCl, which should be very careful to apply. Another classical method is to pass through the stage of obtaining the intermediate disulfide connections, split-level S-S - links with the help of the In this way avoid the use of compounds RSX, but do not avoid subsequent stage of oxidation.

Therefore, the object of the present invention is to avoid these two drawbacks (difficult oxidation and toxicity of the reagent) by offering a direct way of sulfanilamide by exposure of RS(O)X heterocyclic compounds without affecting the overall yield of the reaction and by reducing the number of reaction stages. Currently found, and it is an object of the present invention, the method, which is fully or partly responsible for the achievement of these goals: ease of implementation, profitability and security.

In the European patent applications EP 0295117, 0460940, 0484165 contains numerous examples of the preparation of heterocyclic sulfenylating compounds. In this case, there are two types of methods:

The first group of methods consists in obtaining sulfering connection, which subsequently need to oxidize to obtain the target compound. Getting sulfenylating connections are carried out either by direct exposure of the reagent RSX on heterocyclic compound containing a hydrogen atom in sulfonylurea position, either by impact magyarkanizsa soedinenie connection, or, finally, by the reduction of disulfides in the presence of compounds R I. These different methods are described in European application EP-A-0295117 (see method (b), (d1), (d2) and (d3) on S. 11-I2). Another method, which use a disulfide compounds described in European patent EP-B-1374061.

The second group of methods is the introduction into the interaction sulfenylating connection with a particular connection, such that the product of this reaction is formed by cyclization of heterocyclic sulfenylating connection. For details of these methods again need to refer to European patent application EP A-0295117 (see methods "a" and "c" on S. 11).

In addition, aromatic and nheterocyclic number of recommendations of direct sulfanilamide aromatic hydrocarbons (phenyl cycle). For example, in VI-11. Chem. Soc. Jpn., 46 (1973) 3615, describes the reaction of sulfanilamide of methoxybenzoyl using p-methylphenylsulfonyl in the presence of a catalyst AlCl3. Another reaction of this type is described in GOH, 17, (9) (1981) 1800. The reaction is carried out in the presence of Grignard reagent, which is parametermessagefile, affecting them on aftercooling is which is in the interaction: a derivative of the formula RS(O)X, in which R denotes an alkyl group with 1-4 C-atoms, linear or branched, substituted by one or more identical or different halogen atoms, and X denotes a halogen atom, a hydroxyl group, or one of its salts, dialkylamino group NR2, R3where R2and R3represent alkyl or halogenoalkane group with 1-4 C-atoms, or aryloxy-group in which the aryl portion preferably corresponds to a phenyl group, if necessary substituted by one or more halogen atoms or alkyl or halogenoalkane groups with 1-4 C-atoms; heterocyclic compound Gets selected in the group comprising pyrrole, pyrazoles, imidazoles, oksazolov, isoxazoles, isothiazole, thiazole, triazole, all of these heterocycles Gets if necessary substituted by one or more atoms or groups chosen among halogen, amino, mono - or dialkyl-amino, nitrile, aryl groups substituted by one or more halogen atoms and/or one or more alkyl, halogenoalkane groups or SF5aryl group; provided that R is different from n-butyl, when Het represents pyrrole, and R is different from methyl, when Gets denoted by ycause the pyrrole pyrazoles, imidazoles, and in this case, the connection C is chosen in the group comprising tozilaty, chlorhydrate, mesylates dimethylamine, pyridine, trimethylamine, diethylamine, Isopropylamine or any other primary, secondary or tertiary amine, or gaseous hydrogen chloride, if necessary in the presence of an approximately equimolar amount of p-toluenesulfonic acid, can be added to complete the reaction.

The reagent is selected in the group comprising phosgene COCl2chloroformiate, PCl5or SOCl2in case necessary, can be used for the implementation of the above reactions.

Preferably choose a heterocycle, a substituted amino group. This group then reacts with RS(O)X, giving sulfenamide compound which is then subjected to a rearrangement to obtain heterocyclic compounds containing the amino group, which is located at a carbon atom, and sulfonyloxy group RS(O) on vicinal carbon.

According to one preferred variant of the invention, use connection CF3S(O)X, in which X denotes a chlorine atom. It is known that in this case, the connection CF3S(O)Cl is less toxic than the compound CF3 is the train avoided and this has already been discussed, the stage subsequent oxidation. Moreover, CF3SCl is a gas at room temperature connection, whereas CF3S(O)Cl is the liquid that facilitates the work with this connection.

According to another preferred variant of the invention, use connection CF3S(O)X, in which X represents a group N(CH3)2or N(C2H5)2.

According to a third preferred variant of the invention, use connection CF3(O)X, in which X denotes a hydroxyl group OH or ONa, and in this case the reaction is carried out in the presence of phosgene COCl2or SOCl2.

The way with all its preferred options for implementation are particularly well suited if the heterocycle Het is a compound of the following formula A or B:

< / BR>
< / BR>
in which R1denotes a halogen atom, preferably fluorine, or alkyl or halogenation group, preferably CF3or a group of SF5.

In addition, the invention relates to a method for producing 4-sulfinpyrazone formula:

< / BR>
in which R denotes an alkyl group with 1-4 C-atoms and R1denotes a halogen atom, preferably fluorine, or alkyl or halogenation group, preferably CF3or a group of SF5from compounds of formula:

< / BR>
by exposing the reagent of the formula RS(O)X in which R denotes a linear or branched alkyl group with 1-4 C-atoms, substituted by one or more identical or different halogen atoms, and X denotes a halogen atom, a hydroxyl group, or one of its salts, dialkylamino group NR2, R3where R2and R3denote alkyl or halogenoalkane group with 1-4 C-atoms, or aryloxy-group in which the aryl portion preferably corresponds to a phenyl group, if necessary substituted by one or more halogen atoms or alkyl or halogenoalkane groups with 1-4 C-atoms. Work with a molar excess of the reagent RS(O)X with respect to the above 4-H-pyrazol connection. This excess is of the order of 10-50%, preferably 20-30%.

To complete the above reaction is preferably used as a compound C selected in the group comprising tozilaty, chlorhydrate, mesylates dimethylamine, pyridine, trimethylamine, diethylamine, Isopropylamine Oh gaseous hydrogen chloride, if necessary in the presence of an approximately equimolar amount of paratoluenesulfonyl. The molar ratio between compound C and the heterocyclic compound is preferably 0.5 to 2, and especially 1 to 2. In addition, the reaction is carried out in organic medium in the solvent selected in the group comprising toluene, 1,2-dichloroethane, dichloromethane. The reaction temperature is 0-100oC, preferably 3-60oC, even more preferably 30-55oC.

The reagent is selected in the group comprising phosgene COCl2chloroformiate, PCl5or SOOCl2in case necessary, can be used for the implementation of the above reactions.

How sulfanilamide above pyrazoles even more preferably suitable for the production of 4-sulfinpyrazone formula:

< / BR>
< / BR>
Then either CF3S(O)Cl, CF3S(O)N(CH3)2or CF3S(O)N(C2H5)2or CF3S(O)OH or CF3S(O)ONa with phosgene or SOCl2or CICO2C2H5according to the method and described the preferred options, enter into interaction with 4-H-pyrazol connection one of the following formulas:

< / BR>
< / BR>
In addition, izobreteniya contains a group NH2, formula RS(O)NH-Het, in which Het denotes a heterocyclic radical selected in the group comprising pyrrole, pyrazoles, imidazoles, oksazolov, isoxazoles, isothiazole, thiazole, triazole, all of these generally Gets if necessary substituted by one or more atoms or groups chosen among halogen, amino, mono - or dialkylamino-, nitrile, aryl groups substituted by one or more halogen atoms and/or one or more alkyl, halogenoalkane groups or SF5aryl groups.

More preferably, the compounds of the RS(O)NH-Het, where Het means pyrazol a heterocycle, if necessary substituted by one or more atoms or groups chosen among halogen, amino, mono - or dialkylamino-, nitrile, aryl groups; aryl groups substituted by one or more halogen atoms and/or one or more alkyl, halogenoalkane groups or SF5and where sulfenamide group is in position 5 of the heterocycle, form part of the present invention.

Even more preferably, the invention relates to compounds: 5-(N-trifloromethyl)amino-3-cyano-1-[2,6-dichloro- (4-CF3)

The following examples, data as not limiting the scope of protection of the invention, illustrate the invention and show its implementation in practice.

Example 1. Sulfinpyrasone using CF3S(O)Cl: synthesis of 5-amino-3-cyano-1-(2,6-dichloro-4-triptoreline)-4 - trifloromethyl-pyrazole.

of 8.06 g (25 mmol) of 5-Amino-3-cyano-1-(2,6-dichloro-4 - trifluoromethyl-phenyl)-pyrazole and of 8.15 g (38 mmol) of dimetilmetabolita suspended in 50 ml of toluene. To this mixture quickly add triftormetilfullerenov (5 g, or 32 mmole). The reaction mixture was then heated to 50oC. After reaction for 8 hours at this temperature, the reaction mixture is blown by a current of argon. Then the reaction medium is cooled to 20oC. Add 20 ml of water, after which the precipitate is filtered off, washed with water, and then toluene.

The resulting product is dried by heating in vacuum. So get 9.77, (or yield = 88%) of 5-amino-3-cyano-1-(2,6-dichloro-4 - trifloromethyl-pyrazole with a purity of above 95% (determined by HPLC). Physical and spectral data of the compounds are the following:

So pl. = 196 - 198oC.

NMR analysis:1H-NMR spectrum (CDCl3, TMS): 5 is.; C2: 137,5 M. D.; C3: uniforms, 127.6 ppm; C(CF3): 123 M. D. pyrazol group:

C3: a 126.7 M. D. ; C4: 94,6 M. D.; C5: shall be 152.3 M. D.; C (SP): 111,7 M. D.; C(CF3): 126,3 M. D.

Mass analysis : E1 + M = 436 (35 Cl)

Example 2. Sulfinpyrasone using CF3S(O)Cl : synthesis of 5-amino-3-cyano-1-(2,6-dichloro-4-triptoreline)-4 - trifloromethyl-pyrazole.

0,81 g (2.5 mmol) of 5-Amino-3-cyano-1-(2,6-dichloro-4 - triptoreline)-pyrazole and 0,29 g (2.5 mmol) pyridine-hydrochloride are dissolved in 5 ml of 1,2-dichloroethane.

To this mixture add triftormetilfullerenov (0,5 g (3.2 mmole). The reaction mixture was then heated at 50oC for 10 hours. Proceed then as described in the previous example. The output defined in the calculation of 5-amino-3-cyano-1-(2,6-dichloro-4 - triptoreline)-4-trifloromethyl-pyrazole, is 74%.

Example 3. Sulfinpyrasone using CF3S(O)NMe2: synthesis of 5-amino-3-cyano-1-(2,6-dindar-4-triptoreline)-4 - trifloromethyl-pyrazole.

0,81 g (2.5 mmol) of 5-Amino-3-cyano-1-(2,6-dichloro-4 - triptoreline)-pyrazole and 0.55 g (2.5 mmol) dry (anhydrous) p-toluenesulfonic acid are suspended in 5 ml of toluene. In medium was added N,N - dimethyldiallylammonium what more do as in example 1.

The output defined in the calculation of 5-amino-3-piano-1-(2,6 - dichloro-4-triptoreline)-4-trifloromethyl-pyrazole, 72%).

Example 4. Synthesis of 5-(N-trifloromethyl)amino-3-cyano-1- (2,6-dichloro-4-triptoreline)pyrazole.

Personalfinance included in the present invention, can be obtained and allocated according to the following conditions:

of 3.23 g (10 mmol) 5-Amino-3-cyano-1-(2,6-dichloro-4 - triptoreline)-pyrazole and 3.25 g (15 mmol) of dimetilmetabolita suspended in 20 ml of toluene. The temperature was adjusted to 5oC. Quickly add triftormetilfullerenov (2 g, 13 mmol). Then add toluene solution of dimethylamine (5 mmol).

The reaction mixture was incubated for 30 minutes with stirring at 5oC. then add 50 ml of a simple methyl tert-butyl ether. The formed precipitate is removed by filtration, then washed it. The filtrate Recuperat and washed by extraction with 2 times 10 ml of ice-cold water. The organic phase is concentrated. The resulting residue is crystallized from toluene. So get of 1.75 G. of 5-(N-trifloromethyl) amino-3-cyano-1-(2,6-dichloro-4-triptorelin)pyrazole. physical and spectral SUB>6
, GMDS): 7,06 M. D. (C, 1H); 8,06 m D. c., 2H);

13C-NMR spectrum (acetone-d6, TMS): phenyl group, a C1: 136,2 M. D.; C2: 237 M. D.; C3: 127,4 M. D.; C4: to 135.2 M. D., C(CF3): 123,3 M. D.

pyrazol group: C3: 128,5 M. D.; C4: 105,7 M. D.; C5: 140,7 M. D.; C(SP): 113,5 M. D.; C (CF3): 124,5 M. D.

Example 5. Synthesis of 5-amino-3-cyano-1-(2,6-dichloro-4 - triptoreline)-4-trifloromethyl-pyrazole by rearrangement of personalfinance example 4.

0,109 g (0.25 mmol) of Personalfinance obtained in example 4, and 0,075 g (0.33 mmol) of dimetilmetabolita suspended in toluene. Add a solution of hydrogen chloride in toluene (0.25 mmol HCl). The reaction mixture is heated for 10 hours at 50oC. the Yield, based on 5-amino-3-cyano-1-(2,6-dichloro-4 - triptoreline)-4-triftormetilfullerenov, is 80%.

Example 6. Sulfinpyrasone using CF3S(O)ONa, the synthesis of 5-amino-3-cyano-1-(2,6-dichloro-4-triptoreline)-4 - triftormetilfullerenov.

0,81 g (2.5 mmol) of 5-Amino-3-cyano-1-(2,6-dichloro-4 - triptoreline)pyrazole, 0,815 g (3.8 mmol) of dimetilmetabolita and 0.51 g (of 6.25 mmol) of sodium salt triftormetilfullerenov acid are suspended in 5 ml of toluene. To this is re. Reaction medium was then heated at 50oC for 8 hours. Then proceed as in example 1. The yield, based on 5-amino-3-cyano-1-)2,6-dichloro-4-triptoreline)-4 - trifloromethyl-pyrazole, is 66%.

1. How sulfanilamide heterocyclic compounds, characterized in that a derivative of the formula RS(O)X in which R denotes a linear or branched alkyl group with 1 to 4 C-atoms, substituted by one or more identical or different halogen atoms, and X denotes a halogen atom, a hydroxyl group, or one of its salts, dialkylamino group NR2R3and R2and R3represents an alkyl or halogenoalkane group with 1 to 4 C-atoms; or aryloxy-group in which the aryl portion preferably corresponds to a phenyl group, if necessary substituted by one or more halogen atoms or alkyl or halogenoalkane groups with 1 to 4 C-atoms; enter into interaction with the heterocyclic compound Gets selected in the group comprising pyrrole, pyrazoles, imidazoles, oksazolov, isothiazole, thiazole, triazole, all of these heterocycles Gets if necessary substituted by one or more atoms, the s group, substituted by one or more halogen atoms and/or one or more alkyl, halogenoalkane groups or SF5provided that R is different from n-butyl, when Het represents pyrrole, and R is different from methyl, when Het represents 2,5 - dimethyl pyrrole.

2. The method according to p. 1, wherein Het is chosen in the group comprising pyrrole, pyrazoles, imidazoles, and the fact that for the implementation of the reaction using the compound selected in the group comprising tozilaty, chlorhydrate, mesylates dimethylamine, pyridine, trimethylamine, diethylamine, Isopropylamine, or any other primary, secondary or tertiary amine, or hydrogen chloride, if necessary in the presence of paratoluenesulfonyl.

3. The method according to any of paragraphs.1 or 2, characterized in that the reaction using a reagent selected in the group comprising phosgene CJCl2chloroformiate, PCl5or SOCl2.

4. The method according to any of paragraphs.1 to 3, wherein the heterocycle is substituted by an amino group which reacts with RS(O) X, giving sulfinamide connection, which then regroup to heterocyclic compounds containing amino group located at the carbon atom, and sulfide ACHAT triptorelin group CF3and X denotes a chlorine atom.

6. The method according to any of paragraphs.1 to 4, characterized in that R denotes triptorelin group CF3and X represents a group N(CH3)2or N(C2H5)2.

7. The method according to any of paragraphs.3 or 4, characterized in that R denotes triptorelin group CF3and X denotes a hydroxyl group HE or ONa, and the fact that the reaction is carried out in the presence of phosgene COCl2or SOCl2.

8. The method according to any of paragraphs.1 to 7, wherein the heterocycle Het is a compound of the following formula a or b:

< / BR>
< / BR>
in which R1denotes a halogen atom, preferably fluorine, or alkyl or halogenation group, preferably CF3or a group of SF5.

9. The method of obtaining 4-sulfinpyrazone formulas

< / BR>
in which R denotes alkyl, linear or branched group with 1 to 4 C-atoms, substituted by one or more halogen atoms, equal or different, and R1denotes a halogen atom, preferably fluorine, or alkyl or halogenation group, preferably CF3or a group of SF5, characterized in that the connection formulas

< / BR>
enter in the atoms, substituted by one or more halogen atoms, equal or different, and X denotes a halogen atom, a hydroxyl group, or one of its salts, dialkylamino group NR2R3and R2and R3denote alkyl or halogenoalkane group with 1 to 4 C-atoms, or aryloxy - group in which the aryl portion preferably corresponds to a phenyl group, if necessary substituted by one or more halogen atoms or alkyl or halogenoalkane groups with 1 to 4 C-atoms.

10. The method according to p. 9, characterized in that the reaction using the compound selected in the group comprising tozilaty, chlorhydrate, mesylates dimethylamine, pyridine, trimethylamine, diethylamine, Isopropylamine or any other primary, secondary or tertiary amine, or hydrogen chloride, if necessary in the presence of paratoluenesulfonyl.

11. The method according to any of the p. 9 or 10, characterized in that the reaction using a reagent selected in the group comprising phosgene COCl2chloroformiate, PCl5or SOCl2.

12. The method according to any of paragraphs.9 - 11 4-sulfinpyrazone formulas

< / BR>
< / BR>
by who is B>3S(O) OH or CF3S(O) ONa with phosgene or SOCl5or ClCO2C2H5: 4-H-pyrazol connection formulas

< / BR>
< / BR>
13. Sulfinamide the compounds of formula RS(O)NH - Het, where R denotes a linear or branched alkyl group with 1 to 4 c-atoms, substituted by one or more, same or different halogen atoms, and Het represents pyrazol a heterocycle, if necessary substituted by one or more atoms or groups selected from halogen, amino, mono - or dialkylamino-, nitrile groups, phenyl groups, phenyl groups substituted by one or more halogen atoms and/or multiple alkyl, halogenoalkane groups with 1 to 4 c-atoms, or SF5.

14. Connection on p. 13, where sulfenamide group is in position 5 of the pyrazole nucleus heterocycle.

15. Connection on p. 14, characterized in that R denotes triptorelin group CF3and Het represents 1-[2,6-dichloro-(4-CF3)-phenyl]-3-cyano-4-N-pyrazole.

16. Connection on p. 14, characterized in that R denotes triptorelin group CF3and Het represents 1-[2,6-dichloro(4-SF5)phenyl]-3-cyano-4-N-pyrazole.

 

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EFFECT: compounds and pharmaceutical compositions containing said compounds can inhibit 11β-hydroxysteroid dehydrogenase of the form 1 (11-BETA-HSD-1) and can be used to treat diseases such as type II sugar diabetes type and metabolic syndrome.

17 cl, 99 ex, 1 tbl

FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention elates to novel derivatives of uracil of the formula [I] possessing herbicide activity, a herbicide composition based on thereof and to a method for control of weeds. In derivatives of uracil of the formula [I] the group Q-R3 represents a substituted group taken among:

wherein a heterocyclic ring can be substituted with at least a substitute of a single species taken among the group involving halogen atom, (C1-C6)-alkyl-(C1-C6)-alkoxy; Y represents oxygen, sulfur atom, imino-group or (C1-C3)-alkylimino-group; R1 represents (C1-C3)-halogenalkyl; R2 represents (C1-C3)-alkyl; R3 represents OR7, SR8 or N(R9)R10; X1 represents halogen atom, cyano-group, thiocarbamoyl or nitro-group; X2 represents hydrogen or halogen atom wherein each among R7, R8 and R10 represents independently carboxy-(C1-C6)-alkyl and other substitutes given in the invention claim; R9 represents hydrogen atom or (C1-C6)-alkyl. Also, invention relates to intermediate compounds used in preparing uracil derivatives.

EFFECT: improved preparing method, valuable properties of compounds.

40 cl, 16 sch, 12 tbl, 65 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to method for production of compounds of general formula I wherein R1 represents CN or CSNH2; X represents N or C each R2 and R4 are independently hydrogen or chlorine; R3 represents halogen, haloalkyl, haloalkoxy or SF3; R5 and R6 are independently alkyl; n = 0, 1 or 2. Claimed method includes reaction of compound of formula II , wherein substituents are as defined above; W represent hydrogen, with metal inorganic salt or organic amine to form salt of compound II as intermediate and further reaction of said salt with alkylating agent of formula III wherein R6 is as defined above; Y represents leaving group. In another embodiment compounds of formula I are obtained by reaction of metal inorganic salt or organic base of formula II with abovementioned alkylating agent of formula III.

EFFECT: essentially decreased formation of side products; target products of high purity.

37 cl, 4 ex

FIELD: organic chemistry, pesticides.

SUBSTANCE: invention relates to production of compounds of formula I

, wherein R1 represents CN or CSNH2; X represents N or CR4; R2 and R4 represent hydrogen or chlorine; and R3 represents halogen, haloalkyl, halooxy or SF5. Claimed method includes reaction of compound of formula II

with aqueous acid solution. Also disclosed are method for production of intermediate of formula II, method for production of compound of formula I including step of production of formula II followed by conversion thereof to target compound. Moreover disclosed are two intermediates for production of target products.

EFFECT: new pesticide compounds and method for production thereof.

13 cl, 2 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to 5-substituted alkylaminopyrazole derivatives of formula I , wherein R1 is CN; W is C-halogen; R1 is halogen; R3 is C1-C3-haloalkyl, C1-C3-haloalkoxy; R4 is hydrogen, C1-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, COR8; A is C1-C12-alkylene; R5 is hydrogen, C3-C6-alkenyl, -(CH )qR7 or NR10R11; R5 is C1-C6-haloalkyl; as well as method for animal exogenous and endogenous pest controlling; pesticide composition and application of said compounds for production of veterinary drug. 5-Substituted alkylaminopyrazole derivatives are useful in pest controlling, including insects, arachnids and helminthes, such as nematodes.

EFFECT: new pesticide derivatives.

9 cl, 12 tbl, 20 ex

FIELD: organic chemistry.

SUBSTANCE: invention describes insecticide-acaricide substance used against extoparasites in dogs and cats. Substance represents derivative of phenylpyrazole of the formula (I) wherein in pyrazole structure cyano-group, trifluoromethylsulfenyl group and amino-group are bound at 3, 4 and 5 positions, respectively, and chlorine atoms are bound to phenyl cycle at 2 and 6 positions, and trichlorosilyl group is bound at 4 position. Substance protects dogs and cats against infection with fleas for 65 days after treatment and for 45 days after treatment of cats, and against infection with mites for 35 days, not less. In acute experiment toxicity of substance is characterized by value LD50 above 1300 mg/kg after its administration in stomach to dogs.

EFFECT: valuable properties of substance.

2 ex

FIELD: chemistry.

SUBSTANCE: described are derivatives of 5-substituted alkylaminopyrazoles of formula (I) , where R1 stands for CN, W stands for C-halogen; R2 stands for halogen, R3 stands for (C1-C3)-halogenoalkyl, R4 stands for (C1-C6)-alkyl, A stands for (C1-C12)-alkylene, R5 stands for (C1-C6)-alkyl, R6 stands for (C1-C6)-halogenoalkyl, n equals 2, or their pesticidely acceptable salts. Compounds demonstrate insecticidal activity and parasiticidal activity. The method of obtaining formula (I) is described, including interaction of compound of formula (II) with compound of formula (III) R5-O-A-NH2 and interaction on compound obtained with compound of formula (V) R4-L1.

EFFECT: obtaining derivatives which can be applied as pesticides.

3 cl, 6 tbl, 18 ex

FIELD: medicine.

SUBSTANCE: invention is related to antagonists of serotonin 5-HT6 receptors of common formula 1 and their pharmaceutically acceptable salts and/or hydrates, pharmaceutical compositions, dosage forms and methods of production. Invention also includes new compounds of formula 1.1. In formulae 1 and 1.1 , Ar represents aryl, selected from unnecessarily substituted phenyl or unnecessarily substituted 5-6-member heteroaryl, which contains atom of nitrogen or atom of sulfur and heteroatom; R1 represents atom of hydrogen, unnecessarily substituted C1-C5 alkyl; Ar represents aryl, selected from unnecessarily substituted phenyl or unnecessarily substituted 5-6-member heteroaryl, which contains atom of nitrogen or atom of sulfur as heteroatom; R1 represents atom of hydrogen, which is unnecessarily substituted C1-C5 alkyl; R21,R22, R31, R32 independently from each other represent atom of hydrogen or substituent of aminogroup, selected from unnecessarily substituted C1-C4 alkyl, unnecessarily substituted phenyl, or R31 and R32 together with atom of nitrogen, to which they are bound, create unnecessarily substituted saturated 6-member heterocycle, possibly containing atom of nitrogen in cycle; or R1 together with atom of nitrogen, to which it is bound, and R21 and R22 together with atom of nitrogen, to which they are bound, create substituted pyrimidine cycle. In formula 1.1 R4, R5 and R6 independently from each other represent atom of hydrogen, unnecessarily substituted C1-C3 alkyl or phenyl.

EFFECT: compounds of invention may find application for treatment and prevention of development of conditions and disorders of central nervous system.

13 cl, 11 dwg, 4 tbl, 11 ex

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