The method of producing crimsonlacrosse

 

(57) Abstract:

Usage: as an intermediate in the synthesis of stabilizer thermophotovoltaic degradation of polyamides, rubbers based on silicone elastomer, and also as a stabilizer anti-friction plastic lubricants. The inventive product crimsonadamantsabre. So pl. 331 - 332oC. Exit To 95.5%. Reagent 1: phthalonitrile. Reagent 2: butyl sodium. Reagent 3: phenylenediamine. Reagent 4: urea. Reaction conditions: boiling the reaction mixture for 5 to 6 hours 2 Il., table 2.

The invention relates to the chemistry of macrocyclic compounds, namely, to a method for crimsonadamantsabre - cycle formula

which finds use as an intermediate in the synthesis of stabilizer thermophotovoltaic degradation of polyamides, rubbers based on silicone elastomer, and also as a stabilizer anti-friction plastic residue.

A known method of producing crimsonlacrosse by interaction of n-butanol and metallic sodium with the formation of butyl sodium, interacting with m-phenylenediamine and phthalonitrile.

The closest tech is alicebraga sodium with the formation of butyl sodium. Then to the solution was added m-phenylenediamine and phthalonitrile, the mixture is heated to boiling (115-120aboutC) and boil while stirring with a mechanical stirrer for three hours. The formed precipitate is filtered and washed with dimethylformamide, heated to 60aboutWith, and acetone, heated to 40-50aboutC. the Product is dried at 100aboutC. the Yield of 31.2 kg (65,7% of theoretical in terms of m-phenylenediamine). Crimsonadamantsabre is a dark cherry powdery substance with a melting point 330-332aboutC.

The disadvantage of this method of obtaining a low yield of the target product (65,7%). The resulting macrocycle is different in color and contains significant amounts of organic impurities (phthalocyanine) that cannot be removed by solvents.

Getting crimsonlacrosse these ways is through the formation of intermediate compounds butoxybenzoate. The latter has a tendency to the formation of phthalocyanine, which is usually the main impurity in the macrocycle.

The purpose of the invention to develop ways to obtain crimsonlacrosse, allowing to increase the yield of the target product ive of phthalonitrile, the butyl sodium, and m-phenylenediamine in butanol, and the rst interaction is subjected to phthalonitrile and butyl sodium, after stirring at 25-30aboutTo download m-phenylenediamine, and the addition of urea in the number 0,048-0,064 mol, incubated at 25-30aboutWith 39-40 min and heated the reaction mass for 5-6 hours

Using the proposed method allows to obtain the target product with a yield of 95.5% of not containing phthalocyanine as an impurity (see table).

The identity of the received connection triethylgallium confirmed by melting point and the data of IR and electronic spectra, elementary analysis, and individuality connection using thin-layer chromographic.

P R I m e R 1. 0.06 g (of 0.003 mol) of metallic sodium are dissolved in 70 ml of n-butanol at a temperature of 30aboutC for 0.5 h with the formation of 0.28 g (of 0.003 mol) of butyl sodium. Then contribute to the solution of 6.2 g (0,048 mol) of phthalonitrile, after 0.5 hour of stirring at 30aboutWith a load of 1.75 g (to 0.016 mol) of m-phenylenediamine and 2.9 g (0,048 mol) of urea, incubated 30 min at 30aboutS, after which the mixture is boiled (118-119aboutC) for 5 hours, the Cooled mixture is filtered acetone at Kip is enlargemen).

Red-brown crystalline substance;max513 nm in dimethylformamide. The melting point 331-332aboutC.

WITH30H17N7< / BR>
Found, From 74.9; H 5,0; N 19,9.

Calculated C To 75.7; H 3,7; N 20,6.

P R I m m e R 2. The process is conducted according to the method of example 1, except that when loading add 3.0 g (0.05 mol) of urea. Yield 7.2 g (95%).

Red-brown crystalline substance;max513 nm in dimethylformamide. The melting point 331-332aboutC.

WITH30H17N7< / BR>
Found, 75,6; N 4,15; N 20,4.

Calculated, To 75.7; H 3,7; N 20,6.

P R I m e R 3. The process is conducted according to the method of example 1, except that when loading added 3.8 g (0,064 mol) of urea. The yield of 7.23 g (95,1% ).

Red-brown crystalline substance;max513 nm in dimethylformamide. The melting point 331-332aboutC.

WITH30H17N7< / BR>
Found, To 76.6; H 4,0; N 20,2.

Calculated, To 75.7; H 3,7; N 20,6.

P R I m e R 4. 0.06 g (of 0.003 mol) of metallic sodium are dissolved in 70 mg of n-butanol at a temperature of 25aboutC for 0.5 h with the formation of 0.28 g (of 0.003 mol) of butyl - that of sodium. Then contribute to the solution of 6.2 g (0,048 mol) of phthalonitrile, after 0.5-chasovoj the 0.5 h at 25aboutS, after which the mixture is boiled (118-119aboutC) for 6 hours, the Cooled mixture is filtered and the precipitate washed with acetone at boiling (56aboutC) to conventional Soxhlet extractions and dried at 60aboutC. Output 7,26 g (95.5%).

Red-brown crystalline substance,max513 nm in dimethylformamide. The melting point 331-332aboutC.

WITH30H17N7< / BR>
Found, With A 75.1; H 4,3; N 20,3.

Calculated, To 75.7; H 3,7; N 20,6.

P R I m e R 5. 0.06 g (of 0.003 mol) of metallic sodium are dissolved in 70 ml of n-butanol at a temperature of 30aboutWith over 25 min with the formation of 0.28 g (of 0.003 mol) of butyl sodium. Then contribute to the solution of 6.2 g (0,048 mol) of phthalonitrile, after 25 minutes of mixing at 30aboutWith a load of 1.75 g (to 0.016 mol) of m-phenylenediamine and 3.8 g (0,064 mol) of urea, incubated for 25 min at 30aboutS, after which the mixture is boiled (118-199aboutC) for 6 hours, the Cooled mixture is filtered and the precipitate washed with acetone at boiling (56aboutC) to conventional Soxhlet extractions and dried at 60aboutC. Output 7,26 g (95.5%).

Red-brown crystalline substance;max513 nm in dimethylformamide. The melting point 331-332aboutC.

WITH30H17N7< / BR>
Found, From 75.3; H 4,1; N 20,4.

That macroheterocycles obtained by the proposed method does not contain phthalocyanine as an impurity, confirms the electronic absorption spectrum, recorded on a Specord M 40: there is an intense area maximum 513 nm in dimethylformamide, which is attributed to electronic transitions in chloroform macrocycle, and there is no absorption in the region of 670 nm, typical of phthalocyanine.

Chromatographic analysis on Silufole (TLC) the mixture of chloroform-isopropyl showed the presence of only a single connection, red-brown macrocycle.

Thus, the proposed method of obtaining significantly increase the yield and purity of crimsonlacrosse.

The METHOD of producing CRIMSONLACROSSE the interaction of m-phenylenediamine, phthalonitrile and butyl sodium in boiling butanol, wherein the first subjected to interaction phthalonitrile and butyl sodium, after stirring at 25 - 30oWith add m-phenylenediamine, and the addition of urea in the number 0,048 - 0,064 mole, aged 30 - 40 min at 25 - 30oand then the reaction mass is boiled for 5 - 6 hours

 

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The invention relates to the chemistry of indole derivatives, specifically to the new derived isoindoline General formula I

NR3where both R1is hydrogen or together form a bond;

both R2is phenyl which may be substituted in position 2 or 3 halogen or stands;

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FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to a method for preparing aminoxyl ethers, for example, N-hydrocarbyloxy-derivatives of steric hindranced amines that can be used as light- and/or thermostabilizing organic materials and/or a regulator in the polymerization reaction. Invention describes a method for preparing aminoxyl ethers by interaction of the corresponding N-oxyl derivative with hydrocarbon organic solvent in the presence of organic peroxide and a catalyst representing copper or copper compound, preferably, inorganic compound Cu (I) or Cu (II) as a solution in suitable solvent chosen in the catalytically effective amount. Method provides preparing the end product with the high yield by simplified technological schedule and without using high temperatures.

EFFECT: improved method of synthesis.

15 cl, 2 tbl, 27 ex

Compounds // 2327690

FIELD: chemistry.

SUBSTANCE: description is given of compounds with formula (I) in which A and B represent -(CH2)m- and -(CH2)n- groups respectively; R1 represents hydrogen or C1-6 alkyl; R2 represents hydrogen, C1-6alkyl, C1-6alkoxy, -S-C1-6alkyl, -(CH2)pNR5R6 optionally substituted aryl, heteroaryl or optionally substituted heterocyclyl; R3 represents optionally substituted aryl or optionally substituted heteroaryl; R4 represents hydrogen, C1-6alkyl or halogen; R5 and R6 each independently represents hydrogen or C1-6akyl; Z represents -(CH2)rX-, in which the -(CH2)r- group is bonded to R3 radical, or -X(CH2)r-, in which X is bonded to R3 radical; X represents oxygen, -NR7 group or -CH2- group; R7 represents hydrogen or C1-6alkyl; m and n independently represent an integer, chosen from 1 and 2; p represents 0; r independently represents an integer, chosen from 0 and 1. The invention also relates to use of the given compounds in therapy, in particular, as antipsychotic agents. The result is achieved when using serotonin receptors 5-HT2c, 5-HT2A and 5-HT6.

EFFECT: given compounds have antagonist affinity to serotonin receptors.

12 cl, 9 tbl, 265 ex

FIELD: chemistry.

SUBSTANCE: invention concerns malonamide derivatives of the formulae (IA) or (IB) , and pharmaceutically acceptable acid additive salts of them, where R1, R1',(R2)1,2,3, R3, R4, R14, L, and are such as described in this invention. Also the invention concerns a medicine with inhibition effect on γ-secretase, which can be applied in treatment of Alzheimer's disease.

EFFECT: obtaining new malonamide derivatives with beneficial biological properties.

17 cl, 188 ex

FIELD: chemistry.

SUBSTANCE: described are compounds of formula I in form of free base or acid-additive salt, method of their obtaining, pharmaceutical composition based on them and their application s antagonists of metabotropic glutamate receptors (mGluR5). The invention can be applied in the treatment of the illnesses connected with the disorder of glutamatic signal transfer and the disorder of nervous system partially or completety mediate mGluR5. In general formula T represents 0 or 1, A represents hydroxy, X represents hydrogen, Y represents hydrogen or A forms simple bond with X or Y; ring methylene group directly bound with CH(X)-, can be dimethylated; R0 represents hydrogen, C1-C4alkyl, C1-C4alkoxy, halogen, cyano, and R represents -COR3, -COOR3 or -SO2R6,where R3 represents C1-C4alkyl, C3-C7cycloakyl, and R6 represents C1-C4alkyl, C3-C7cycloakyl, or R represents -C(O)R3, where R3 represents furanyl, trifluoromethyl, pyridinyl, morpholinyl or methylpiperasinyl; or -C(O)OR3, where R3 represents tetrahydrofuranyl, R' represents hydrogen, C1-C4alkyl or 4-methoxybenzyl, and R" represents hydrogen or C1-C4alkyl, or R' and R" together form group -CH2-(CH2)p-, where p represents 0, 1 or 2, one of symbols n and p does not represent 0, on condition that R0 does not represent hydrogen, trifluoromethyl and methoxy, when m represents 1, n represents 0, A represents hydroxy, X and Y both represent hydrogen, R represents COOEt and R' and R" together form group -(CH2)2-.

EFFECT: efficient application of compounds for treatment of diseases caused by disturbance of transduction of glutamatergic signal and diseases of nervous system.

8 cl, 11 ex

FIELD: chemistry.

SUBSTANCE: invention relates to new compounds with general formula (I) , where R1 and R2 are independently chosen from hydrogen, halogen, nitro, alkyl, alkylaryl and XYR5; X and Y are independently chosen from O and (CR6R7)n; R3 represents hydrogen, alkyl or M; M represents an ion, chosen from aluminium, calcium, lithium, magnesium, potassium, sodium, zinc or their mixture; Z represents CR4; R4 is chosen from hydrogen, halogen, alkyl, alkylaryl and XYR5; R5 is chosen from aryl, substituted aryl, heteroaryl and substituted heteroaryl; R6 and R7 are independently chosen from hydrogen and alkyl; n is an integer from 1 to 6; at least one of R1 and R2 represents XYR5, and at least one of X and Y represents (CR6R7)n. The invention also pertains to the method of increasing concentration of D-serine and/or reducing concentration of toxic products of D-serine oxidation under the effect of DAAO in mammals, involving introduction into a subject of a therapeutically effective amount of a formula I compound, to the method of treating schizophrenia, treating or preventing loss of memory and/or cognitive ability, to the method of improving learning ability, method of treating neuropathic pain, as well as to a pharmaceutical composition, with DAAO inhibitory activity, based on these compounds.

EFFECT: obtained are new compounds and a pharmaceutical composition based on these compounds.

27 cl, 4 tbl, 72 ex

FIELD: chemistry.

SUBSTANCE: invention relates to novel compounds of general formula where: R1 denotes -OR1', -SR1", 6-member heterocycloalkyl with one O atom and possibly one N atom, phenyl or 5-member heteroaryl with two N atoms, 6-member heteraryl with one N atom; R1'/R1" denote C1-6-alkyl, C1-6-alkyl substituted with a halogen, -(CH2)x-C3-6cycloalkyl or -(CH2)x-phenyl; R2 denotes S(O)2-C1-6-alkyl, -S(O)2NH-C1-6-alkyl, CN; denotes the group: , and where one extra N atom of the nucleus of an aromatic or partially aromatic bicyclic amine may be present in form of its oxide ; R3 - R10 denotes H, halogen, C1-6-alkyl, C3-6cycloalkyl, 4-6-member heterocycloalkyl with one N or O atom, 6-member heterocycloalkyl with two O atoms or two N atoms, 6-8-member heterocycloalkyl containing on N atom or one O or S atom, 5-member heteroaryl with two or three N atoms, 5-member heteroaryl with one S atom, in which one carbon atom may be also substituted with N or O, 6-member heteroaryl with one or two N atoms, C1-6-alkoxy, CN, NO2, NH2, phenyl, -C(O)-5-member cyclic amide, S-C1-6-alkyl, -S(O)2-C1-6-alkyl, C1-6-alkyl substituted with halogen;C1-6-alkoxy substituted with halogen, C1-6-alkyl substituted with OH, -O-(CH2)y-C1-6-alkoxy, -O(CH2)yC(O)N(C1-6-alkyl)2, -C(O)-C1-6-alkyl, -O-(CH2)x-phenyl, -O-(CH2)x-C3-6cycloalkyl, -O-(CH2)x-6-member heterocycloalkyl with one O atom, -C(O)O-C1-6-alkyl, -C(O)-NH-C1-6-alkyl, -C(O)-N(C1-6-alkyl)2, 2-oxa-5-aza-bicyclo[2.2.1]hept-5-yl or 3-oxa-8-aza-bicyclo[3.2.1]oct-8-yl; R' and R'" in group (e) together with -(CH2)2- with which it is bonded can form a 6-member ring; R, R', R" and R"' independently denote H, C1-6-alkyl; and where all groups - phenyl, cycloalkyl, cyclic amine, heterocycloalkyl or 5- or 6-member heteroaryl, as defined for R1, R1', R1" and R3 - R10, can be unsubstituted or substituted with one or more substitutes selected from OH, =O, halogen, C1-6-alkyl, phenyl, C1-6-alkyl substituted with halogen, or C1-6-alkoxy; n, m o, p, q, r, s and t = 1 , 2; x =0, 1 or 2; y = 1 , 2; and their pharmaceutically acceptable acid addition salts.

EFFECT: compounds have glycine transporter 1 inhibiting activity, which enables their use in a pharmaceutical composition.

20 cl, 2 tbl, 12 dwg, 382 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention relates to field of organic chemistry and pharmaceutics and deals with novel anti-hypertension salt of general formula [(R1-COO-)·(H3N-R2)], where R1 is inhibitor of angiotensin-converting enzyme, selected from group, which consists of perindoprilat, ramiprilat, spiraprilat, benazeprilat, moexiprilat, trandalaprilat, fosinoprilat, enalaprilat, zofenoprilat or lisinopril, and R2 -calcium channel blocker, selected from group, consisting of amlodipine, lacidipine, felodipine, isradipine.

EFFECT: invention ensures reduction of therapeutic doses and side effects.

3 dwg, 2 tbl, 3 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: claimed invention relates to compounds of formula (IC-2), to their pharmaceutically acceptable salts, N- oxides or solvates. In formula (IC-2) Z represents carbomoyl group, which can be replaced with C1-4 alkyl or hydroxy; R1 represents C1-8 alkyl or C1-8 alkoxy; R4 and R4-1 each independently represent hydrogen atom or C1-8 alkyl; m represents integer number from 1 to 5, when m equals 2 or larger number, all R1 can have same or different values. Invention also relates to compounds, representing 1-({6-[(2-methoxy-4-propylbenzyl)oxy]-1-methyl-3,4-dihydro-2-napthlenyl}methyl)-3-azetidinecarbonic acid, 1-({6-[(4-isobutyl-2-methoxybenzyl)oxy]-1-methyl-3,4-dihydro-2-naphthalinyl}methyl)-3- azetidinecarbonic acid and other, given in formula of claimed invention.

EFFECT: obtaining pharmaceutical composition, which has agonistic activity with respect to EDG-1, EDG-6 and/or EDG-8, containing as active component invention compound, to method of prevention and/or treatment of disease, conditioned by EDG-1, EDG-6 and/or EDG-8 invention compounds, to method of prevention and/or treatment of disseminated sclerosis and method of immune reaction suppression and/or induction of lymphopenia, to application of invention compounds for obtaining medication for prevention and/or treatment of disease, conditioned by EDG-1, EDG-6 and/or EDG-8, to application of compounds for obtaining medication for prevention and/or treatment of disseminated sclerosis, to application of compounds for obtaining immunodepresant and/or medication inducing lymphopenia and to crystal forms of some individual compounds.

17 cl, 10 dwg, 5 tbl, 251 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to new compounds of formula , wherein: R1 means phenyl, 6-member heteroaryl containing one or two atoms N as heteroatoms and wherein said phenyl, 6-member heteroaryl is optionally substituted by one R7; R2 means phenyl, 6-member heteroaryl containing one or two atoms N as heteroatoms and wherein each of said phenyl or 6-member heteroaryl is optionally substituted by one R7; R3 means halogen R7 independently means halogen, OR8, phenyl, 6-member heteroaryl containing one or two atoms N as heteroatoms wherein any phenyl or heteroaryl can be optionally substituted by one R14; R14 means halogen, OR8; R8 independently means C1-6alkyl; m is equal to 1; in the form of a free base or its pharmaceutically acceptable salt, and to their pharmaceutically acceptable salt.

EFFECT: compounds possess BACE inhibitory activity.

8 cl, 6 tbl, 136 ex

FIELD: chemistry.

SUBSTANCE: copolycarbonate contains an isomeric mixture of the following formulae as a repeating monomer unit:

,

where R1 is hydrogen or alkyl with 1-10 carbon atoms and R2 is an alkyl with 1-10 carbon atoms or, if needed, a phenyl or benzyl substituted with hydrogen and/or an alkyl with 1-10 carbon atoms, respectively; and diphenol of formula:

, where R3 and R4 denote hydrogen, an alkyl with 1-18 carbon atoms, an alkoxy with 1-18 carbon atoms, a halogen, respectively, if needed, a substitued aryl or arylalkyl, and X is a single bond, -SO2-, -CO-, -O-, -S-, an alkylene with 1-6 carbon atoms, an alkyidene with 2-5 carbon atoms or a cycloalkylidene with 5-6 carbon atoms, which can be substituted with an alkyl with 1-6 carbon atoms, an arylene with 6-12 carbon atoms, which, if needed, is condensed with aromatic ring groups containing heteroatoms.

EFFECT: high glass transition temperature, high operating temperature and improved adhesion to metal.

9 cl, 9 ex

FIELD: organic chemistry, medicine.

SUBSTANCE: invention relates to new derivatives of phenylpiperazine of the formula (I): , wherein X represents 1) group of the formula (1): , wherein S1 means hydrogen, halogen atom; S2 and S3 mean independently of one another hydrogen atom, (C1-C6)-alkyl, phenyl or benzyl; S4 means two hydrogen atoms, oxo-group; S5 means hydrogen atom (H), (C1-C4)-alkyl; Y means CH2, oxygen atom (O), sulfur atom (S); or 2) group of the formula (2): , wherein S1 has above given values; R means hydrogen atom (H), (C1-C4)-alkyl, (C2-C6)-alkoxyalkyl, (C2-C4)-alkenyl or (C2-C4)-alkynyl; or 3) group of the formula (3): wherein S1 has above given values; Z means CH2, oxygen atom (O), nitrogen atom (N); or 4) group of the formula (4): , wherein S1 has above given values; or 5) group of the formula (5): , wherein S1 has above given values; A means oxygen atom (O), nitrogen atom (N) linked with piperazine ring at position 5 or 8; or 6) group of the formula (6): , wherein S1 has above given values; S6 and S7 mean hydrogen atom or oxo-group; or 7) group of the formula (7): , wherein one of dotted line can represent a double bond; S1 has above given values; P = T = Q mean nitrogen atom or P = T mean nitrogen atom; Q means CH or CH2; or P = Q mean nitrogen atom; T means CH, CH2, CH-CH3, C-CH3; or P means nitrogen atom; T means CH, CH2; Q represents sulfur atom; m = 2-6; n = 0-2; R5 and R6 mean independently of one another hydrogen atom (H), (C1-C3)-alkyl; or R5 + R6 represent group -(CH2)p- wherein p = 3-5; R7 means (C1-C3)-alkyl, (C1-C3)-alkoxy-, halogen atom, cyano-group; or R6 + R7 (R7 at position 7 of indole ring) mean group -(CH2)q wherein q = 2-4, and their salts. Compound of the formula (I) elicit high affinity both to dopamine D2-receptor and to serotonin reuptake site that allows their applying in treatment of the central nervous system diseases.

EFFECT: valuable medicinal properties of compounds.

5 cl, 3 tbl, 4 sch, 8 ex

FIELD: organic chemistry, heterocyclic compounds, medicine, pharmacy.

SUBSTANCE: invention relates to nitrogen-containing heterocyclic derivatives of the formula (I): A-B-D-E (I) wherein A means 5- or 6-membered heteroaryl comprising one or two nitrogen atoms in ring; B means ethenylene; D mean phenylene; E means group -N(COR)-SO2-G wherein G means phenyl; R means 5- or 6-membered heteroaryl or heteroarylmethyl comprising one or two nitrogen atoms in ring, or group -(CH2)n-N(R5)R6 wherein n means a whole number from 1 to 5; R5 and R6 are similar or different and mean: hydrogen atom, (C1-C6)-alkyl, hydroxyalkyl, aminoalkyl; or R5 and R6 in common with nitrogen atom can form 5-7-membered cyclic amino-group -N(R5)R6 that can comprise, except for nitrogen atom, also oxygen, sulfur or nitrogen atom as a component forming the ring, or their N-oxides. Compounds of the formula (I) elicit anticancer activity and can be used in medicine.

EFFECT: valuable medicinal properties of compounds.

10 cl, 1 tbl, 24 ex

FIELD: organic chemistry, pharmacy.

SUBSTANCE: invention relates to new substituted derivatives of pyrrole of the formula (I): wherein R1 and R1' mean independently hydrogen atom (H) or (lower)-alkyl, unsubstituted or substituted (lower)-alkoxy-group; R2 means hydrogen atom (H), nitro-group (-NO2), cyano-group (-CN), halogen atom, unsubstituted (lower)-alkyl or substituted with halogen atom or (lower)-alkoxy-group; R2' means thiazolyl, thiophenyl, isothiazolyl, furanyl and pyrazolyl that is unsubstituted or substituted with (lower)-alkyl, pyrimidinyl, unsubstituted morpholinyl, unsubstituted pyrrolidinyl and imidazolyl that is unsubstituted or substituted with (lower)-alkyl, unsubstituted piperidinyl or piperazinyl that is unsubstituted or substituted with (lower)-alkyl, or ethoxy-group substituted with imidazolyl, or its pharmaceutically acceptable salt. Compounds of the formula (I) inhibit cell proliferation in G2/M phase of mitosis that allows their using in the pharmaceutical composition.

EFFECT: valuable biological properties of compounds.

36 cl, 4 sch, 1 tbl, 21 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to new biologically active derivatives of dihydrobenzo[b][1,4]diazepine-2-one. Invention describes derivatives of dihydrobenzo[b][1,4]diazepine-2-one of the general formula (I): wherein X means a simple bond or ethynediyl group wherein if X means a simple bond then R1 means cyano-group, halogen atom, lower alkyl, (C1-C3)-cycloalkyl, (lower)-alkoxyl, fluoro-(lower)-alkyl or it means pyrrole-1-yl that may be free or substituted with 1-3 substitutes taken among the group consisting of fluorine, chlorine atom, cyano-group, -(CH2)1-4-hydroxyl group, fluoro-(lower)-alkyl, lower alkyl, -(CH2)n-(lower)-alkoxyl, -(CH2)n-C(O)OR'', -(CH2)1-4-NR'R'', hydroxy-(lower)-alkoxyl and -(CH2)n-COR'R'', or it means free phenyl or phenyl substituted with one or two substitutes taken among the group consisting of halogen atom, lower alkyl, fluoro-(lower)-alkyl, (lower)-alkoxyl, fluoro-(lower)-alkoxyl and cyano-group; if X means ethynediyl group then R1 means free phenyl or phenyl substituted with 1-3 substituted taken among the group consisting of halogen atom, lower alkyl, fluoro-(lower)-alkyl, (C3-C6)-cycloalkyl, (lower)-alkoxyl and fluoro-(lower)-alkoxyl; R2 means -NR'R'', fluoro-(lower)-alkoxyl or 3-oxopiperazin-1-yl, pyrrolidin-1-yl, or piperidin-1-yl wherein their rings are substituted optionally with R''; R' means hydrogen atom, lower alkyl, (C3-C6)-cycloalkyl, fluoro-(lower)-alkyl or 2-(lower)-alkoxy-(lower)-alkyl; R'' means hydrogen atom, lower alkyl, (C3-C6)-cycloalkyl, fluoro-(lower)-alkyl, 2-(lower)-alkoxy-(lower)-alkyl, -(CH2)2-4-di-(lower)-alkylamino-group, -(CH2)2-4-morpholinyl, -(CH2)2-4-pyrrolidinyl, -(CH2)2-4-piperidinyl or 3-hydroxy-(lower)-alkyl; Y means -CH= or =N-; R3 means halogen atom, lower alkyl, fluoro-(lower)-alkyl, (lower)-alkoxyl, cyano-group, -(CH2)n-C(O)OR'', -(CH2)1-4-NR'R'' or it means optionally substituted 5-membered aromatic heterocycle that can be substituted with halogen atom, fluoro-(lower)-alkyl, fluoro-(lower)-alkoxyl, cyano-group, -(CH2)n-NR'R'', -(CH2)n-C(O)OR'', -(CH2)n-C(O)NR'R'', -(CH2)n-SO2NR'R'', -(CH2)n-C(NH2)=NR'', hydroxyl, (lower)-alkoxyl, (lower)-alkylthio-group or lower alkyl that is optionally substituted with fluorine atom, hydroxyl, (lower)-alkoxyl, cyano-group or carbamoyloxy-group; n means 0, 1, 2, 3 or 4, and their pharmaceutically acceptable additive salts. Also, invention describes a medicinal agent as antagonist of mGlu receptors of group II based on compounds of the formula (I). Invention provides preparing new compounds eliciting valuable biological properties.

EFFECT: valuable medicinal properties of compounds.

17 cl, 496 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to maleic acid substituted bis-indolylimides of the formula (I):

wherein R means -PO3R1R2, -CHR3OCOR4, -CHR3OCO2R4, -CHR3OCONHR4, -COR4; R1 and R2 are taken among the group consisting of H, Na being they are similar but if one among R1 or R2 means H then other means sodium atom (Na); R3 means H or methyl; R4 is taken among the group including (lower)-alkyl that can be substituted optionally with one substitute taken among the group including -CO2R5, -NR6R7, polyethtylene glycol of the formula R9(OCH2CH2)nOH wherein n means an average number from 2 to 1500 with average molecular mass from 500 to 5000 Da and wherein R9 means carboxyl or lower alkyl, (C1-C10)-alkenyl, piperidine, phenyl that can be substituted optionally with one or two substitutes taken among the group including alkoxy-group, alkyl that in turn can be substituted with dialkylamino-group under condition that R4 can not mean (lower)-alkyl in the group -COR4; R5 means H, lower alkyl; R6 and R7 mean H, lower alkyl; or their pharmaceutically acceptable salts. Compounds of the formula (I) possess anti-proliferative effect and can be used in pharmaceutical composition for parenteral administration.

EFFECT: valuable biological and medicinal properties of compounds.

16 cl, 1 tbl, 19 ex

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