The method of obtaining derivatives of 2-anilinopyrimidines

 

(57) Abstract:

Usage: in agriculture as having fungicidal and insecticidal activity. The invention is a method of obtaining derivatives of 2 - anilinopyrimidines General formula where R1and R2-independently of one another denote hydrogen, halogen, C1-C3-alkyl, C1-C2- halogenated, C1-C3- alkoxy or C1-C3- halogenoalkane, R3is hydrogen, C1-C4-alkyl, or substituted hydroxy-group C1-C4- alkyl, cyclopropyl or replaced by stands cyclopropyl; R4-C3-C6-cyclopropyl or substituted identically or differently with stands and/or by halogen, up to three times, (C3-C6-cycloalkyl. Reagent I: salt phenylquinoline formula where Aanion of a mineral acid or guanidine of the formula . Reagent II: diketone: R3C(O)CH2C(O)R4; the cyclization is carried out at a temperature of 60 to 160C.

The invention relates to a method for producing derivatives of 2-anilinopyrimidines - new biologically active compounds which can be used in agriculture as having fungicidal and insecticidal activity.

ako these compounds have not a high fungicidal activity/ insecticidal activity they are missing.

The purpose of the invention is a method of obtaining new derivatives of 2-anilinopyrimidines of low/ high fungicidal activity and manifesting/ in addition/ insecticidal activity.

This goal is achieved by the described method of obtaining derivatives of 2-anilinopyrimidines General formula

NH (I) where R1and R2independently from each other mean a hydrogen/ halogen/ S1-C3-alkyl/ S1-C2-halogenated/ S1-C3-alkoxy or C1-C3-halogenoalkane;

R3-hydrogen/ S1-C4is alkyl or substituted with halogen or hydroxy-group1-C4-alkyl/ cyclopropyl or replaced by stands cyclopropyl;

R4-C3-C6-cyclopropyl or substituted identically or differently with stands and/or halogen/ up to a triple/ S3-C6-cycloalkyl/ which is/ that salt phenylquinoline formula

NHC A(IIa) which means the anion of a mineral acid or guanidine of the formula

NHC (IIB) is subjected to cyclization with a diketone of the formula

R3- - CH2- R4(III) at a temperature of 60-160With subsequent isolation of the target product.

Examples of receiving the R>
10 g (51 mmol) of acid carbonate phenylquinoline and 9/7 g (77 mmol) of 1-cyclopropyl-1/3-butandione heated under stirring for 6 h to 110With/ this starts the emission of carbon dioxide increases with the continuation of the reaction. After cooling to room temperature, dark brown emulsion is mixed with 50 ml of diethyl ether/ washed twice with water (20 ml/ dried over sodium sulfate/ filtered and evaporated the solvent. The remaining dark brown oil (10/1 d) clear columnar chromatography through silica gel (diethyl ether/toluene 5:3). After evaporation of the eluting mixture of brown oil is crystallized and recrystallized from a mixture of diethyl ether/petroleum ether at 30-50C. Receive light brown crystals; so pl. 67-69C. Output 8/55 g (38 mmol) (74/5% of theory).

Example 2 Obtaining 2-aniline-4-formylmethylene-6-cyclopropylamino (connection 1/02).

NH

11/7 g (59/2 mmol) of acid carbonate phenylquinoline and 13/3 g (62/2 mmol) 1-cyclopropyl-3-formerdirector-1/3-propanedione in 40 ml of ethanol is heated under stirring to the boiling point of phlegmy/ while carbon dioxide increases with the duration of the first broadcast/ washed twice with water (30 ml/ dried over sodium sulfate/ filtered and the solvent evaporated. The remaining dark brown oil (17 g) is cleaned by columnar chromatography over silica gel (toluene/ethyl acetate 5:2). After evaporation of the eluting mixture remains reddish-brown oil with a refractive index of n2D01/5815. Yield 15 g (48 mmol/ 81/1% of theory).

Example 3. Getting 2-aniline-4-formyl-6-cyclopropylamino (compound 2.1).

NH

12/3 g (39/3 mmol 2-aniline-4-formerdirector-6-cyclopropylamino/ 4 g (39/3 mmol) of concentrated hydrochloric acid and 75 ml of water is heated under vigorous stirring for 14 h at 500From and after adding 2 g (19/6 mmol) of concentrated hydrochloric acid is stirred for further 24 h at this temperature. After cooling to room temperature the suspension beige add 50 ml of ethyl acetate and neutralized by adding 7 ml of 30% sodium hydroxide. The ethyl acetate solution is then separated/ dried over sodium sulfate/ filtered and the solvent evaporated. To clean the brown coloured solid is recrystallized from 20 ml of isopropanol with the addition of activated carbon. Yellowish crystals melting at 112-114C. Output 7/9 g (33 mmol/ 84% of theory).

Example 4. Pool) 2-aniline-4-formyl-6-cyclopropylamino in 350 ml of absolute methanol for 15 min under stirring at room temperature/ portions add 2/3 g (60 mmol) of sodium borohydride/ when this reaction mixture with hydrogen gas is heated to the 28C. After 4 h, the reaction mixture is acidified with precapitalism 10 ml of concentrated hydrochloric acid; added dropwise to 120 ml of 10% aqueous sodium hydrogen carbonate solution, and then immediately diluted with 250 ml of water. The precipitation is filtered/ dried/ dissolve completely in 600 ml of diethyl ether under heating/ treated with activated charcoal and filtered. Transparent filtrate is evaporated until Muti/ diluted with petroleum ether and filtered light yellow crystalline dust; so pl. 123-125C. Output 10/8 g (44/8 mmol/ 75/9% of theory).

b) 5/9 g (23 mmol) of 2-aniline-4-methoxymethyl-6-cyclopropylamino/ received from phenylquinoline and 1-cyclopropyl-4-methoxy-1/3-butandione/ dissolved in 200 ml dichloromethane and cooled to -68C. To easily painted to the solution under vigorous stirring slowly for 30 min added dropwise 6/8 g (27 mmol) of bartered/ directly after that, remove the cooling bath and stirred for further 2 h at room temperature. After adding 150 g of ice water precipitated crude product is filtered and recrystallized from methanol with the use of activated carbon. Light yellow crystals melt imethyl-6-cyclopropylamino and 0/4 g (50 mmol) of pyridine in 350 ml of diethyl ether are added dropwise within 30 min under stirring 15/6 g (75 mmol) of thienylboronic in 50 ml of diethyl ether. After 2 h stirring at room temperature add 0/4 g (50 mmol) of pyridine and heated 5 hours to the boiling temperature of phlegmy. After cooling to room temperature, add 200 ml of water with addition of 140 ml of a saturated solution of sodium bicarbonate set the value of pH 7. After separation of the phases diethyl ether, washed twice with water (100 ml/ dried over sodium sulfate/ filtered and the solvent evaporated. The remaining brown oil is cleaned by columnar chromatography through silica gel (toluene/chloroform/diethyl ether/petroleum ether); so bales. 50-70From: 5/3/1/1. After evaporation of the eluting mixture yellow oil was diluted with a mixture of diethyl ether); so bales. 50-70With and put in the cold for crystallization. Yellow crystalline dust melts at 77/5-79/5C. Output 9/7 (32 mmol) and 64% of theory.

Example 5. Getting 2-phenylamino-4-vermeil-6-cyclopropylamino

(connection 1/34).

NH

a) 3/9 g (12/8 mmol) 2-phenylamino-4-bromacil-6-cyclopropylamino/ 1/5 g (12/8 mmol) is dried by sublimation of potassium fluoride and 0/3 g (1/13 mmol) of 18-crown-6-ether are heated in 50 ml of acetonitrile 40 hours to the boiling temperature of phlegmy. After this the add 0/75 g (13 mmol) is dried by sublimation of potassium fluoride and 0/1 g (0/38 mmol) of 18-crown-6-ether, and optionally heated 24 hours to the boiling temperature of phlegmy. After cooling to room temperature, the suspension is mixed with 150 ml of diethyl ether/ washed three times with water (20 ml/ dried over sodium sulfate/ filtered and the solvent evaporated. The remaining brown oil is cleaned by columnar chromatography through silica gel (toluene/chloroform/diethyl ether/petroleum ether; so bales. 50-70With/ 5/3/1/1. After evaporation of the eluting mixture yellow oil make in 10 ml of petroleum ether (so Kip. 50-70C) and exposed to the cold for crystallization. Yellow crystals melt at 48-52C. Output 2/1 g (8/6 mmol)/ 67/5% of theory.

b) To a suspension 9/1 g (37/8 mmol) 2-phenylamino-4-hydroxymethyl-6-cyclopropylamino in 80 ml of dichloromethane under stirring for 1 h dropwise added slowly 6/1 g (37/8 mmol) diethylaminoacetate in 15 ml of dichloromethane. After adding 50 ml of ice water are added dropwise 50 ml of 10% aqueous solution of sodium bicarbonate. After the carbon dioxide organic phase is separated and the aqueous phase is twice extracted with dichloromethane portions 20 ml. United solutions dichloromethane washed with water (15 ml)/ dried over sodium sulfate/ filtered and evaporated the solvent.RM/diethyl ether; so Kip. 50-70With/ 5/3/1/1. After evaporation of the eluting mixture yellow oil was diluted with 20 ml of petroleum ether (so pl. 50-70C) and exposed to the cold for crystallization. Yellowish crystals which melt at 50-52C. Output 4/9 g (20/1 mmol/ 53% of theory).

Example 6. Obtaining 2-hydroxy-4-methyl-cyclopropylamine.

HO .

6 g (100 mmol) of urea and 12/6 g (100 mmol) of 1-cyclopropyl-1/3-butadiona at room temperature are mixed in 35 ml of ethanol with 15 ml of concentrated hydrochloric acid. After 10 days of standing at room temperature, evaporated on a rotary evaporator with a bath temperature of maximum 45C. the Residue is dissolved in 20 ml of ethanol/ very quickly precipitated hydrochloride of the reaction product. With stirring, add 20 ml of diethyl ether/ precipitated white crystals are filtered and washed with a mixture of ethanol and diethyl ether and dried. As a result of evaporation of the filtrate and recrystallization from a mixture of ethanol and diethyl ether (1:2) receive an additional amount of the hydrochloride. White crystals which melt at temperatures above 230C. Output hydrochloride 12/6 g (67/7 mmol/ 67/5% of theory).

Example 7. Poluchkoi-4-methyl-6-cyclopropylamino under stirring at room temperature contribute in a mixture of 100 ml (1/1 mmol) of phosphorus oxychloride and 117 g (0/89 mmol) diethylaniline/ the temperature rises to 63C. After heating for 2 h to 110With cooled to room temperature and the reaction mixture under stirring transferred into a mixture of ice water and methylene chloride. The organic phase is separated and washed until neutral with saturated aqueous solution of sodium bicarbonate. After evaporation of the solvent receive 116/4 g oil/ which consists of the reaction product and diethylaniline. Department of diethylaniline and purification of the crude reaction product is carried out using columnar chromatography through silica gel (hexane/diethylacetal 3:1). After a few days zakristallizuetsya colourless oil has a refractive index of n2D51/5419. Output 35/7 g (0/21 mmol/ 87/5% of theory); so pl. 33-34C.

Example 8. Obtain 2-(m-forgenerating)-4-ethyl-6-cyclopropylamino (connection 1/63).

NH

The solution 5/5 g (50 mmol) 3-foronline and 9/3 g (55 mol) of 2-chloro-4-methyl-6-cyclopropylamino in 100 ml of ethanol under stirring by adding 5 ml of concentrated hydrochloric acid adjusted to pH 1, and then immediately heated for 18 hours to the boiling temperature of phlegmy.

After cooling to room temperature the brown emulsion deviationism ether portions 150 ml. The United extracts washed with 50 ml of water/ dried over sodium sulfate/ filtered and evaporated the solvent. The remaining yellowish crystals are purified by recrystallization from a mixture of diisopropyl ether (petroleum ether); so bales. 50-70C. the White crystals melt at 87-89C. Output 8/3 g (34 mmol/ 68% of theory).

Example 9. Obtain 2-(p-forgenerating)-4-methyl-6-cyclopropylamino (connection 1/21).

FNH

24/8 g (0/115 mmol) hydrogen 4-fortunelounge and 17/5 g (0/138 mmol) 1-cyclopropyl-1/3-butandione in 150 ml of methanol is heated under stirring for 24 h at the boiling point of phlegmy/ moreover, the formation of carbon dioxide over time is clearly reduced. The obtained dark brown transparent solution process is still warm activated carbon/ filtered and the filtrate evaporated on a rotary evaporator before the separation of the crystalline mass and with stirring, poured into 500 ml of water. The precipitated crystals are filtered/ washed with a small amount of cold ethanol/ dried and recrystallized from a mixture of diisopropyl ether and petroleum ether (50-70C). Painted beige crystals melt at 89-91C.


62/2 g (0/3 mmol) of 95% hydrogen phenylquinoline placed in 300 ml isopropanol and under stirring at an external temperature of 124With heated up to the boiling point of phlegmy 78With/ and formed suspension/ painted beige. Within 40 min was added dropwise 42/1 g (0/3 mmol) 1-(2-methylcyclopropyl)-1/3-butandione/ while immediately begins energetic emissions of carbon dioxide. Upon completion of addition the reaction mixture is heated for 6 hours under stirring at the boiling temperature of phlegmy and after lowering the ambient temperature distilled 200 ml of isopropanol using a capacitor. After removal of the heat when the internal temperature of 60When mixing, slowly add 100 ml of water to the brown solution after adding water slowly begins to thicken. After 12 hours stirring at room temperature, cooled for 1 h to +5With in the next two hours to +3C. Precipitated slurry of crystals is filtered/ washed with 40 ml of a cold mixture (1:1) isopropanol and water and dried white crystals; so pl. 73-74C. Output 51/4 g (0/215 mmol/ exit from theory 75/3%).

Example 11. Getting 2-phenylethylamine under stirring at room temperature is mixed with 6 ml of acetic acid. After heating to 50With added dropwise within 0/5 h under stirring 28 g (0/2 mmol) 1-cyclopropyl-1/3-pentanedione and with stirring is heated further 2 h to 150C. After cooling to room temperature the solvent is evaporated under vacuum and with stirring, the dark brown reaction mixture was poured into 500 ml of water. After establishing pH 9 with a little dilute alkali (NaOH) twice the aqueous phase is extracted with diethyl ether portions 150 ml/ United extracts are washed with 200 ml of water and dried over sodium sulfate/ filtered and the ether evaporated. The remaining oil distil in a high vacuum; so bales. 125-129With 1 PA. Yellow oil after some time, hardens; so pl. 42-45C.

All the compounds of formula I or their physico-chemical constants/ received described by way of/ are given in table.1.

In the following table. 2/ 3 and 4 as examples named intermediate compounds of the proposed invention.

The biological tests derived 2-anilinopyrimidines/ received the described way.

Biological examples.

Example 1. Action against Venturia inaequalis on the shoots of Apple trees. Re the broth for sprinkling (0/006% active substance)/ prepared from wettable active component. After 24 hours the treated plants were infected with a spore suspension of fungi. The plants are then incubated for 5 days at 90-100% relative humidity/ in the next 10 days kept in the greenhouse at 20-24C. within 15 days after infection was assessed lesion scabs.

Connection table.1 showed against Venturia inaequalis good activity (lesion less than 20%). So/ connections NN 1,01, 1,06, 1.12, 1.13, 1.21, 1.28, 1.34, 1.35, 1.36, 1.38, 1.44, 1.45, 1.48, 1.51, 1.54, 1.56, 1.58, 1.63, 1.68, 1.71, 1.78, 1.86 and 1.87 reduce the defeat of Venturia to 0-10%. But untreated infected control plants were amazed however at 100%.

Example 2. Action against Botrytis cinerea on fruit-apples. Residual-protective action.

Artificially damaged apples were processed so that the broth for sprinkling (0/002% active substance)/ received from wettable powder of the active substance is/ was sprayed on the damaged area. Processed fruits immediately after it was infected with a spore suspension of the fungus and during the week kept at high humidity at approximately the 20C. When the assessment was calculated moldy damaged areas, and therefore it was determined fungicidal effect ispytyvaemoj the/ for example/ join NN 1.01, 1.04, 1.06, 1.08, 1.12, 1.13, 1.20, 1.21, 1.22, 1.28, 1.31, 1.33, 1.34, 1.35, 1.36, 1.38, 1.40, 1.43, 1.44, 1.45, 1.48, 1.51, 1.54, 1.56, 1.58, 1.63, 1.65, 1.67, 1.68, 1.71, 1.78, 1.81, 1.86, 1.87 and 1.88 reduced defeat Botrytis to 0-10% . But untreated infected control plants had defeated Botrytis 100%.

Example 3. Action against Erysiphae graminis on barley.

a) Residual-protective action.

Barley plants with a height of about 8 cm were sprayed with a broth for sprinkling (0/006% active substance)/ prepared from wettable powder of the active substance. After 3-4 hours the treated plants were suffused with spores of the fungus. The infected barley plants were placed in a greenhouse at a temperature of about 22With and assessed the damage by the fungus in 10 days.

Connection table. 1 showed against Erysiphae good activity (lesion less than 20%). So/ for example/ join NN 1.1, 1.06, 1.12, 1.13, 1.21, 1.28, 1.34, 1.35, 1.36, 1.38, 1.44, 1.45, 1.48, 1.51, 1.20, 1.63, 1.78, 1.86 and 1.87 reduced defeat Erysiphae to 0-10%. But untreated infected control plants/ on the contrary/ had lesions 100%.

Description of the experience.

Comparison of the activity of biologically active substances according to the invention with the prior art.

1. Connection (PS/5-16701/1+2/+E)

X1 Connection 1.01

X2NH Izvestnye connection

Y1NH Connection 1 (2)

Y Connection 35 (2)

Y3Compound 34 (2)

Y4Compound 37 (1)

Y5Compound 36 (1)

The experiment

Action against Nilaparvata lugeus when applied in water to the rice plants.

The rice plants Varietat Nohrin 29/ grown for 3 weeks in porcelain pots/ added to distilled water aqueous emulsion/ prepared with the active substance/ subject test/ with a concentration of 100 ppm.

Through 1/ 2 and 3 weeks after application, the rice plants were infected with N-3 nymphs in the amount of 20 pieces.

The experiment was carried out in the greenhouse at 26With 60% relative humidity with light duration 16 PM

After 5 days estimated the number of victims tested animals (% mortality)/ compared to untreated control samples.

The results are presented below.

The tests showed that the compounds according to the invention have a higher fungicidal activity/ than connection-analogs/ in addition they possess insecticidal action. However, they have low toxicity and have good compatibility with respect to plants.

The WAY GENDER is other - hydrogen, halogen, C1- C3-alkyl, C1- C2-halogenated,1- C3-alkoxy or C1- C3-halogenoalkane;

R3is hydrogen, C1- C4-alkyl, or substituted with halogen or hydroxy-group1- C4-alkyl, cyclopropyl or replaced by stands cyclopropyl;

R4- C3- C6-cycloalkyl or substituted identically or differently from one to three times the stands and/or halogen WITH3- C6-cycloalkyl,

characterized in that the salt phenylquinoline General formula

NHC A< / BR>
where is the anion of a mineral acid, or a guanidine of the General formula

NHC

subjected to cyclization with a diketone of General formula

R3- - CH2- R4< / BR>
if necessary, in a solvent at 60 - 160oWith subsequent isolation of the target product.

 

Same patents:

The invention relates to methods of producing derivatives of 2-anilinopyrimidines or acid additive salts of novel biologically active compounds, which can find application in agriculture

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FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention describes substituted benzoylcyclohexanediones of the general formula (I):

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EFFECT: valuable properties of compounds.

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EFFECT: valuable herbicide properties of compounds.

23 cl, 17 sch, 9 tbl, 11 ex

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EFFECT: improved preparing method, valuable properties of compounds.

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EFFECT: improved preparing method, valuable properties of compounds.

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FIELD: agriculture, fungicides.

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Herbicidal agent // 2271659

FIELD: organic chemistry, agriculture, herbicides.

SUBSTANCE: invention relates to herbicidal agent containing compound of general formula I wherein X represents residue X1 or X2 and Z, R1 and R2 are as defined in claim of invention, and additional active substance selected from group containing bromoxynil, dicamba, flufenacete, metolachlor, atrazine, pendimethaline, imazetapir, iodosulfuron, nicosulfuron, 2-amino-4-(1-fluoro-1-methyl)-6-(3-phenyl-1-cyclobuthyl-1-propylamino)-1,3,5-triazine and N-[(4,6-dimethoxy-pyrimidine-2-yl)-aminocarbonyl]-2-dimethylamino-carbonyl-5-formyl-benzenesulfonamide. Compound of formula I and additional active substance are taken in mass ratio of 1:20-10:1, respectively.

EFFECT: agent of high herbicidal activity.

6 cl, 15 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to an intermediate compound, i. e. tert.-butyl-(E)-(6-{2-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]-pyrimidine-5-yl}-(4R,6S)-2,2-dimethyl[1,3]dioxane-4-yl]acetate that can be used in synthesis of compound of the formula (IV)

eliciting inhibitory effect on activity of HMG-CoA-reductase and, therefore, can be used for preparing pharmaceutical agents for treatment, for example, hypercholesterolemia, hyperproteinemia and atherosclerosis. Also, invention relates to a method for preparing indicated intermediate compound by reaction of the new parent compound - diphenyl-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidine-5-ylmethyl]phosphine oxide with tert.-butyl-2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxane-4-yl]acetate in the presence of a strong base in simple ether or aromatic solvents or their mixtures at temperature in the range from -200C to -900C. Also, invention relates to a method for preparing of compound of the formula (IV) wherein R1 means hydrogen atom or pharmaceutically acceptable cation and to a method for preparing intermediate compounds of the formula (VI):

wherein each P1 and P2 represents independently (C1-C4)-alkyl or group:

and wherein P3 represents (C1-C8)-alkyl. Applying new intermediate compounds and proposed methods provide enhancing quality and yield of compounds.

EFFECT: improved preparing methods.

9 cl, 1 tbl, 8 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to new derivatives of 5-phenylpyrimidine or their pharmaceutically acceptable acid-additive salts that elicit properties of antagonists of neuropeptide receptor neurokinin-1 (NK-1). This allows their applying for treatment of such diseases as Alzheimer's disease, cerebrospinal sclerosis, attenuating syndrome in morphine withdrawal, cardiovascular alterations and so on. Compounds of invention correspond to the general formula (I):

wherein R1 means hydrogen or halogen; R2 means hydrogen, halogen atom, (lower)-alkyl or (lower)-alkoxy-group; R3 means halogen atom, trifluoromethyl group, (lower)-alkoxy-group or (lower)-alkyl; R4/R4' mean independently hydrogen atom or (lower)-alkyl; R5 means (lower)-alkyl, (lower)-alkoxy-group, amino-group, hydroxyl group, hydroxy-(lower)-alkyl, -(CH2)n-piperazinyl substituted optionally with lower alkyl, -(CH)n-morpholinyl, -(CH2)n+1-imidazolyl, -O-(CH2)n+1-morpholinyl, -O-(CH2)n+1-piperidinyl, (lower)-alkylsulfanyl, (lower)-alkylsulfonyl, benzylamino-group, -NH-(CH2)n+1N(R4'')2, -(CH2)n-NH-(CH2)n+1N(R4'')2, -(CH2)n+1N(R4'')2 or -O-(CH2)n+1N(R4'')2 wherein R4'' means hydrogen atom or (lower)-alkyl; R6 means hydrogen atom; R2 and R6 or R1 and R6 in common with two ring carbon atoms can represent -CH=CH-CH=CH- under condition that n for R1 is 1; n means independently 0-2; X means -C(O)N(R4'')- or -N(R4'')C(O)-. Also, invention relates to a pharmaceutical composition.

EFFECT: valuable medicinal properties of compounds.

15 cl, 4 sch, 86 ex

FIELD: organic chemistry, biochemistry, chemical technology, pharmacy.

SUBSTANCE: invention relates to (E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(me-thylsulfonyl)amino]pyrimidin-5-yl]-(3R,5S)-3,5-dih-ydroxyhept-6-enoic acid crystalline salts wherein salt represents ammonium, methyl ammonium, ethyl ammonium, diethanol ammonium, tris-(hydroxymethyl)methyl ammonium, benzyl ammonium, 4-methoxybenzyl ammonium, lithium or magnesium salt possessing property of HMG CoA-reductase inhibitor. Also, invention relates to a pharmaceutical composition comprising crystalline salt in mixture with a pharmaceutically acceptable diluting agent or vehicle an to a method for preparing crystalline salt. Method involves addition of corresponding amine or a base to a solution of (E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(me-thylsulfonyl)amino]pyrimidin-5-yl]-(3R,5S)-dihydro-xyhept-6-enoic acid in acetonitrile or ethyl acetate medium. The advantage of crystalline salts involves the possibility for enhancing purity and homogenicity of compounds, the possibility for re-crystallization and preparing the pure amorphous form and enhancing stability of the form.

EFFECT: improved preparing method.

15 cl, 9 dwg, 10 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to R-2-aminoarylpropionic acid amides and pharmaceutical composition comprising thereof that can be used for prophylaxis and inhibition of recruiting and activation of leukocytes, and in treatment of pathologies directly dependent on indicated activation. Invention proposes compound of the general formula (1): wherein A, q, Ph and R have corresponding values, or its pharmaceutically acceptable salt. Also, invention describes a method for preparing amide of the formula (1) and pharmaceutical composition used in prophylaxis of leukocytes activation. Invention provides the development of pharmaceutical composition that can be used for prophylaxis and treatment of damaged tissues caused by enhancing activation of neutrophile granulocytes (polymorphonuclear leukocytes) in inflammation foci. Also, the invention relates to R-enantiomers 2-(aminoaryl)-propionylamides of the formula (1) that can be used for suppression of neutrophyles hemotaxis caused by IL-8. Also, compounds of this invention can be sued in treatment of psoriasis, ulcerous colitis, glomerulonephritis, acute respiratory insufficiency and rheumatic arthritis.

EFFECT: valuable medicinal properties of compounds.

8 cl, 16 ex

FIELD: organic chemistry, pharmaceuticals.

SUBSTANCE: invention relates to heterocyclic compounds of general formula I with PGl2 receptor agonist activity. In formula R1 and R2 represent independently optionally substituted phenyl; Y represents N, N-O or CR5; Z represents N or CR6; A represents NR7; D represents alkylene or alkenylene; or A and D may together form divalent group; E represents phenylene or direct bond, or D and E may together form divalent group; G represents O, S, SO, SO2; R3 and R4 represent hydrogen atom or alkyl; Q represents carboxyl, alkoxycarboxyl, tetrazolyl, carbamoyl or -CONH-SO-R10 group. Prostaglandin I2(PGl2) is potent inhibitor of platelet aggregation and may be effectively used in treatment of vascular diseases, arteriosclerosis, hypertension, etc.

EFFECT: new compounds and drugs for platelet aggregation inhibition and treatment of vascular and other diseases.

15 cl, 3 tbl, 109 ex

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