1-piperidino-3-(4-pertenece)isopropyl ester of n - methylcarbamates acid as a biocidal additive for lubricating oils
(57) Abstract:The use of the invention as biocidal additives for lubricating oils. The inventive product 1-piperidino-3-(4-pertenece)isopropyl ester of N-methylcarbamates acid f-ly BF C16H23FN2O3so pl. 170°C, yield 80%. Reagent 1: 1-piperidino-3-(4-pertenece)propanol-2. Reagent 2: methyl isocyanate. Reaction conditions: - CCl4in the presence of triethylamine at 30 - 35°C for 7 h 1 table. The invention relates to new chemical compound, specifically to 1-piperidino-3-(4-pertenece)-isopropyl ether, N-methylcarbamyl acid of the formula I
which can find use as a biocidal additive for lubricating oils.At the present time, it is important to study the scientific, technical, economic and environmental problems of the biological damage of materials and development of measures of struggle against them. Particularly relevant combat biodamage lubricating oils. So the microorganisms getting into the oil and directly consuming hydrocarbon components of the oil or acting on them by the products of their metabolism, causing oils irreversible changes and reduce their perfo is In oils precipitation is formed and resinous substances, that can lead to the deterioration of the mode of engine operation (1).To prevent microbiological destruction oils in their composition is administered special antimicrobial additive is a biocide. As antimicrobial additives for lubricating oils of the proposed 8-oksihinolina and its derivatives, naphthenate metals, compounds containing arsenic, tin, mercury, boron compounds, etc. (2-4). However, most of them have several disadvantages that make it difficult to use in practice, significant toxicity to humans, narrow antimicrobial spectrum of action and adaptation of microorganisms. Therefore, the synthesis and study as biocidal additives to lubricating oils, new classes of organic compounds is of great interest.The aim of the invention is the expansion of the range of substances exhibiting antimicrobial activity in lubricating oils, and the effectiveness of their actions.This goal is achieved by the fact that as antimicrobial additives for lubricating oils offers a 1-piperidino-3-(p-pertenece)-isopropyl ester N-methylcarbamyl acid, which is synthesized by the interaction of 1-piperidino-3-(p-pertenece)-propanol-2 metalizing ether p-terfenol (5) with piperidine according to the method, described in (6).Synthesis of 1-piperidino-3-(p-pertenece)-isopropyl ester was carried out as follows.P R I m m e R. To a mixture of 25.4 g (0.1 mole) 1-piperidino-3-(p-pertenece)-propane - La-2, 60 ml of dry carbon tetrachloride and 0.5 g of triethylamine (catalyst) with stirring, added dropwise to 8 g (1,4 mol) of methyl isocyanate and stirred for 7 h at 30-35aboutC. Upon completion of the reaction the reaction mass is distilled off, the excess methyl isocyanate, triethylamine, carbon tetrachloride and the final product was recrystallized from isooctane.Received 24 g (yield 80%) of the product so pl. 170aboutC.Found, %: C 61,93; H 7,10; N 9,15.C16H23FN2O3.Calculated, %: C 61,93; H 7,41; N 9,03.Building 1-piperidino-3-(p-pertenece)-isopropyl ether methylcarbamyl acid has been proved by IR and PMR spectroscopy.In the infrared spectrum has absorption bands-NHC(O)-groups with a frequency of 1270 cm-1and ester group-C(O)-O - in the field 1225 cm-1. The absorption band 1715 cm-1characterizes the relationship of C=O in esters, and the absorption bands with frequencies 1205 and 1030 cm-1belong to the C-O and C-O-N-Bond NH p the second ring.In the PMR spectrum includes signals of protons disubstituted benzene ring in the area 8726 M. D. proton of NH group manifests a complex signal in the area 5,35-5,80 m D. Quadropole with chemical shift 4,94 M. D. refers to the resonance of the proton group SN.1-Piperidino-3-(p-pertenece)-ISO-propyl ether, N-methylcarbamyl acid was tested as antimicrobial additives to oil M-11. The tests were carried out according to GOST 9.05.75 and GOST 9.08.77 method of zonal diffusion using the following microorganisms:
Bacteria: Pseudomonas aeruginosa Mycobacterium lacticolum.Fungi: Aspergillus niger, Chatomium globosum, Cladosporium resinae, Penicillum chrysogenum, Trichoderma viride and yeast-like microorganisms.For growing bacterial cultures was used mastopathy agar (MPA), and for fungi and yeast - wort-agar (C/a).The investigated compound and reference pentachlorophenolate sodium were added to the oil M-11 in weight percent units. Oil M-11 is a blend of distillate and residual (not less than 30%) oils phenol purification from sulfur crudes.For the tests in Petri dishes poured nutrient medium in the amount of 20-25 ml and gave it to harden. Seeding of microorganisms was carried out on the surface of the pit is ubinas 4-5 mm, which added 0.5 to 0.8 ml oil M-11 with the specified connection. Then the Petri dishes were placed in a thermostat and kept for 2 days when using bacteria and 3-4 days for fungi at a certain humidity and temperature 302aboutC.Similar tests were carried out with reference connection - pentachlorophenolate sodium.The effectiveness of antimicrobial action 1-piperidino-3-(p-pertenece)-isopropyl ester N-methylcarbamyl acid was determined by the value of the diameter of zone of inhibition of growth of microorganisms.The results are given in the table.From the table it is seen that the proposed compound effectively inhibits the growth of microorganisms, affecting oil M-11. The necessary concentration of this compound is less than when using pentahlorfenolyata sodium. So, pentachlorophenol sodium at a concentration of 0.25% does not inhibit the growth of both bacterial and fungal microflora. Our connection not only at a concentration of 0.25%, but when 0,12% effectively inhibits the growth of microorganisms, affecting oil M-11. It should also be noted that the test compound does not adversely affect the physico-chemical properties of mA is raminosoa acid is recommended as a biocidal additive for lubricating oils. 1-Piperidino-3-(4-pertenece)isopropyl ester of N-methylcarbamates acid formula
< / BR>as biocidal additives for lubricating oils.
FIELD: organic synthesis.
SUBSTANCE: invention provides compounds of general formula I:
in which R1 represents H, halogen, OCH3, or OH; R2 represents (a) -X-(CH2)n-CH2-N(R4)R5, where (i) X represents NH or S; n is integer from 1 to 4; R4 and R5, the same or different, represent C1-C4-alkyl, H, -CH2C≡CH, or -CH2CH2OH; or R4 and R5, together, form nitrogen-containing five- or six-membered cycle or heteroaromatic cycle; or where (ii) X represents O; n is integer from 1 to 4; one of R4 and R5 is CH2C≡CH, or -CH2CH2OH and the other H or C1-C4-alkyl; or R4 and R5, together, form imidazole cycle or nitrogen-containing six-membered cycle or heteroaromatic cycle; or R2 represents (b) -Y-(CH2)nCH2-O-R5, where (i) Y represents O; n is integer from 1 to 4; and R6 represents -CH2CH2OH or -CH2CH2Cl; or where (ii) Y represents NH or S; n is integer from 1 to 4; and R6 represents H, -CH2CH2OH, or -CH2CH2Cl; or R2 represents (c) 2,3-dihydroxypropoxy, 2-methylsulfamylethoxy, 2-chloroethoxy, 1-ethyl-2-hydroxyethoxy, or 2,2-diethyl-2-hydroxy-ethoxy; R3 represents H. halogen, OH, or -OCH3. Claimed compounds are novel selective estrogen receptor modulators. Invention also discloses pharmaceutical composition and a method for production of tissue-specific estrogenic and/or antiestrogenic effect in patient, for whom indicated effect is required.
EFFECT: increased choice of estrogen receptor modulators.
19 cl, 7 tbl, 11 ex
FIELD: organic chemistry, medicine, ophthalmology, pharmacy.
SUBSTANCE: invention relates to new derivatives of nitrogen-containing heterocyclic compounds of the general formula (I): wherein X1, X2, X3, X4 and X5 mean -CH2 or one of them represents -NH and another X1-X5 represent -CH2; k = 0, 1 or 2; when t = 2, then radicals R1 are similar or different; R1 represents direct or branched (C1-C8)-alkyl or (C1-C8)-alkoxy-group; A means phenyl or pyridinyl; R2 means hydrogen atom (H), hydroxyl, halogen atom, (C1-C6)-alkyl, (C1-C6)-alkoxy-group; n = 0, 1-4; radicals R2 are similar or different, when n > 1; p = 0 or 1-5; Y means -OC(O); Z means -CH, or to their pharmaceutically acceptable salts. Compounds of the formula (I) possess agonistic activity with respect to muscarinic receptors and can be used in medicine as medicinal preparations for treatment of neurodegenerative diseases or diseases associated with increased intraocular pressure.
EFFECT: valuable medicinal properties of derivatives.
6 cl, 1 tbl, 2 dwg, 16 ex
SUBSTANCE: there are described 2-(R)-phenylpropionic acid derivatives of formula (1) and their pharmaceutically acceptable salts where R' is chosen from H, OH and provided R' represents H, R is chosen from H, C1-C5-alkyl, C3-C6-cycloalkyl, C1-C3-alkoxy, thiazolyl, substituted CF3, the remained formula -CH2-CH2-Z-(CH2- CH2O)nR', where n is equal to 2, and Z represents oxygen, the remained formula - (CH2)n-NRaRb, the remained formula SO2Rd, provided R' represents OH, R is chosen from C1-C5alkyl. The compounds are applied to inhibit chemotactic activation of neutrophils (PMN leukocytes) induced by interaction of interleukine-8 (IL-8) and membrane receptors CXCR1 and CXCR2. The compounds are applied to prevent and treat the pathologies generated by specified activation. There are also described application of the compounds for manufacturing of medicinal agents for treating psoriasis, nonspecific ulcerative colitis, melanoma, angiogenesis, chronic obstructive pulmonary disease (COPD), bullous pemphigoid, rheumatoid arthritis, idiopathic fibrosis, glomerulonephritis and to prevent and treat the damages caused by ischemia and reperfusion, the pharmaceutical composition and method for making the compounds of formula (1) where R' represents H and R - group SO2Rd.
EFFECT: higher clinical effectiveness.
8 cl, 3 tbl, 11 ex
SUBSTANCE: invention is related to compound of formula (I), (values of radicals are described in formula of invention) or its pharmaceutically acceptable salts, to methods of its production, pharmaceutical composition, which contains it. Application of invention is described for manufacturing of medicinal agent intended for provision of inhibiting action in respect to HDAC in warm-blooded animal, in production of agent used for treatment of malignant tumor. Method is also described for provision of inhibiting action in warm-blooded animal.
EFFECT: compounds have inhibiting activity in respect to HDAC.
15 cl, 17 tbl, 24 ex
SUBSTANCE: invention relates to novel anthranilic acid derivatives having inhibitory effect on production of matrix metalloprotease 13 of formula 1 , where R1 is a hydrogen atom or carboxy protective group selected from C1-3alkyl; R2 is phenyl, C3-6cycloalkyl, saturated or unsaturated 5-6-member heterocyclic group containing 1-3 heteroatoms selected from N, O, S, which can be condensed with phenyl, which can be optionally substituted with C1-6alkyl, C1-6alkoxy, acetyl, acetoxy, halogen, halogenC1-6alkyl, nitro group, hydroxyl group, CN, amino group, phenyl, saturated or unsaturated 5-6-member heterocyclic group containing 1-4 heteroatoms selected from N, O, S, which can be disubstituted with C1-6alkyl; R3 is phenyl, C3-6cycloalkyl, C5cycloalkenyl, saturated or unsaturated 5-6-member heterocyclic group containing 1-3 heteroatoms selected from N, O, S, which can be condensed with phenyl (except benzoxazole), which can be optionally substituted with C1-6alkyl, C1-6alkoxy, phenyl, acetyl, halogen, halogenC1-6alkyl, halogenC1-6alkoxy, nitro group, hydroxyl group, hydroxyC1-6alkyl, CN, acetylamino, ketone, phenoxy, benzoyl, benzyl, amino group, which can be disubstituted with C1-6alkyl, carboxy group, C1-6alkylsufonyl group or pyrrolyl; X1 is a carbonyl group or sulfonyl group; X2 is a C1-3alkylene, C2-3alkenylene or C2-3alkynylene group which can be optionally substituted with C1-3alkyl, or a bond; provided that when X1 is a sulfonyl group and X4 is a bond, X2 is a C1-3alkylene, C2-3alkenylene or C2-3alkynylene group which can be optionally substituted with C1-3alkyl; X3 is an oxygen atom or a bond; and X4 is a group with general formula -X5-X6- or -X6-X5-, where the bond on the left side of each formula is bonded to R3; and X5 is an oxygen atom, a sulphur atom, an imino group which can be optionally protected or a bond; X6 is a C1-4alkylene, C2-3alkenylene or C2-3alkynylene group or a bond, as well as to their pharmaceutically acceptable salts. The invention also relates to a matrix metalloprotease 13 production inhibitor and a therapeutic agent for making a medicinal agent for treating rheumatoid arthritis.
EFFECT: possibility of making a medicinal agent for treating rheumatoid arthritis.
8 cl, 7 tbl, 633 ex
FIELD: medicine, pharmaceutics.
SUBSTANCE: claimed invention relates to compound of general formula (I) and its pharmaceutically acceptable salts. In general formula (I) , Y represents group -CONH(Q)- or -NHCONH(Q)-; Q represents 6-member aromatic ring or 5-10-member heteroaromatic ring, containing one or two N heteroatoms or two O heteroatoms; R represents hydrogen, halogen, linear or branched (C1-C6)alkyl; (C1-C6)alkoxy; di-(C1-C6)alkylamino, 5-member heteroaromatic ring, containing one O or S heteroatom; 6- or 9-member heteroaromatic ring, containing one or two N heteroatoms; phenyl, mono- or disubstituted with halogen, (C1-C6)alkyl, halogeno(C1-C6)alkyl, (C1-C6)alkoxy, acyl; hydroxy; piano; di-(C1-C6)alkylamino, acylamino' carbamoyl; X represents group : where Z represents CH2, N or O; m represents integer number from 1 to 3; p is equal 0, 1; R" is selected from group, consisting of di-( C1-C6)alkylaminocarbonyl, (C1-C6)alkyl, acyl. Invention also relates to pharmaceutical composition, containing as active ingredient, invention compound, to application of invention compound for manufacturing pharmaceutical composition, to method of inhibition of nicotinic acetylcholine receptor α7.
EFFECT: obtaining compound, which possesses agonistic activity with respect to nicotinic acetylcholine receptor (nAChR) α7.
7 cl, 2 tbl, 4 dwg, 270 ex
SUBSTANCE: invention relates to chemical derivatives of adamantane and specifically to a novel method of producing 2-(2-alkyl(dialkyl)amino)adamantyl-alkyl(aryl)ketones of general formula R=-NHCH3: R1=Et,-CH2-CH=CH2; : R1=Me, Et,-CH2-CH=CH2, Ph,-CH2Ph; : R1= Me, Etwhich can be used as intermediate products in synthesis of certain biologically active substances. The novel method involves reacting 2-alkylamino(dialkylamino)-2-cyanoadamantanes from the group: 2-methylamino-2-cyanoadamantane, 2-N-piperidino-2-cyanoadamantane, 2-N-morpholino-2-cyanoadamantane with Grignard reagents from the group: methylmagnesium iodide, ethylmagnesium bromide, allylmagnesium chloride, phenylmagnesiuim bromide, benzylmagnesium chloride in a medium of dry diethyl ether or a tetrahydrofuran-ether mixture in molar ratio of reagents equal to 1:2-2.03, respectively, at temperature 30-45°C for 4-5 hours.
EFFECT: wider range of adamantane derivatives, design of a method for synthesis of novel adamantane derivatives with high output.
SUBSTANCE: invention relates to a method of producing cycloalkylamines of general formula Alk-R, where
, , , , , , , , , . The method is realised by reacting a cyclic ketone with an amine derivative and formic acid in the presence of a catalyst. The cyclic ketones used include cyclopentanone, cyclohexanone and 2-adamantanone, and the amine derivative used is formamide, cyclohexylamine, piperidine, morpholine, piperazine, 2-aminoethanol, 1,2-ethylenediamine, and the catalyst used is copper nanoparticles. The process is carried out in molar ratio ketone: amine derivative: HCOOH equal to 1:3-4:5-10, at temperature 100°C for 3-9 hours. The copper nanoparticles can be obtained in situ, as well as beforehand.
EFFECT: high output of cycloalkylamines under milder conditions for carrying out the process.
3 cl, 11 ex
SUBSTANCE: invention refers to new compounds of the formula (I) that are characterized by the properties of M3 muscarine receptor antagonist that is applicable in treatment or prevention of the disease or state (the abnormity of) which includes activity of the M3 muscarine receptor such as respiratory diseases. In the formula (I) A is represented by the oxygen atom or the group -N(R12)-; (i) R1 is represented by C1-C6-alkyl or the hydrogen atom; and R2 is represented by the hydrogen atom or the group -R5, -Z-Y-R5, -Z-NR9R10, -Z-NR9CO-R5 or -Z-CO2H; and R3 is absent or is represented by C1-C6-alkyl, and in this case the nitrogen atom to which it is bound is represented by tetradic nitrogen and bears a positive charge; or (ii) R1 and R2 together with nitrogen to which they are bound form heterocycloalkyl ring; the mentioned ring is displaced by the group -Y-R5 or -Z-Y-R5, and R3 is absent or is represented by C1-C6-alkyl, and in this case the nitrogen atom to which it is bound is represented by tetradic nitrogen and bears a positive charge; R4 is represented by the formula group (a), (b), (c) or (d); Z is represented by C1-C16-alkylene group; Y is represented by the link or the oxygen atom; R5 is represented by C1-C6-alkyl, aryl, phenyl condensed with C3-C6cycloalkyl, phenyl condensed with heterocycloalkyl, heteroaryl, aryl(C1-C8-alkyl)-, heteroaryl(C1-C8-alkyl)-, C3-C6cycloalkyl or heteroC3-C6cycloalkyl group; R6 is represented by C1-C6-alkyl or the hydrogen atom; n and m equal 0; R8a and R8b are independently chosen from the group consisting of aryl, phenyl condensed with heterocycloalkyl, heteroaryl, C1-C6-alkyl, C3-C6cycloalkyl; R8c is represented by -OH or C1-C6-alkyl; R9 and R10 are represented independently by the hydrogen atom, C1-C6-alkyl, aryl, phenyl condensed with heterocycloalkyl and other components mentioned in the invention formula.
EFFECT: new compounds applicable in treatment or prevention of the disease or state (the abnormity of) which includes activity of the M3 muscarine receptor such as respiratory diseases.
10 cl, 49 ex
SUBSTANCE: invention relates to an amine compound of formula (I), pharmaceutically acceptable addition salts, hydrates or solvates thereof, having immunodepressive effect , where R - H or P(=O)(OH)2; X - O or S; Y denotes -CH2CH2- or -CH=CH-; Z denotes C1-5-alkylene, C2-5-alkenylene or C2-5-alkynylene; R1 denotes CF3, R2 denotes C1-4-alkyl, substituted with OH or halogen; R3 and R4 independently denotes H < or C1-4-alkyl; A denotes optionally substituted C6-10-aryl, heteroaryl containing 5-10 ring atoms, where 1 or 2 atoms are selected from N, O and S, C3-7-cycloalkyl optionally condensed with optionally substituted benzene, or heterocycloalkyl containing 5-7 ring atoms, where 1 or 2 atoms are selected from N and O, where said substitutes are selected from C1-4-alkylthio, C1-4-alkylsulphanyl, C1-4-alkylsulphonyl, C2-5-alkylcarbonyl, halogen, cyano, nitro, C3-7-cycloalkyl, C6-10-aryl, C7-14-aralkyloxy, C6-10-aryloxy, optionally substituted with oxo or halogen, C2-3-alkyleneoxy, C3-4-alkylene or C1-2-alkylenedioxy, optionally substituted with halogen C1-4-alkyl or C1-4-alkoxy.
EFFECT: novel compound which is effective in reducing the level of lymphocytes in peripheral blood, suppresses tissue breakdown and exhibiting less side effects, such as bradycardia, is disclosed.
20 cl, 237 ex, 2 tbl
FIELD: technological processes of cold plastic metalworking and machining.
SUBSTANCE: proposed composition contains the following components, mass-%: vegetable component (in terms of dry substance), 5-40; triethanol amine, 0.20-0.46; ethylene glycol, 0.60-0.82; sodium dodecyl sulfate, 0.20-0.25; sodium hydrophosphate, 0.20-0.25; oxyquinoline, 0.20-0.22; the remainder being water. For preparation of vegetable component, solid fraction of pig manure is preliminarily subjected to washing-off for complete removal of animal excrements, after which extraction by steam condensate is carried out at temperature of 150-170 C and pressure of 0.5-0.7 Mpa continued for 60-120 minutes and then extract is evaporated at temperature of 100-110 C to concentration of 40-70 mass-%.
EFFECT: enhanced stability; reduced corrosion activity and toxicity; improved tribological characteristics; facilitated procedure and low cost of method.
SUBSTANCE: composition contains oil which contains naphthene base oil on a mineral base, paraffin base oil on a mineral base and/or paraffin base oil obtained via Fischer-Tropsch synthesis, a copper passivator, and from 0.001 to less than 0.1 wt % sulphur-based organic compound as an antiwear additive. The composition can also contain a phenol or amine antioxidant. The composition of the base oil and antiwear additive undergoes purification with bleaching clay with subsequent addition of the copper passivator and an optional antioxidant. The composition is used as electrically insulating oil, particularly transformer oil.
EFFECT: high oxidative stability with low content of additive.
21 cl, 6 tbl, 2 dwg, 4 ex
SUBSTANCE: invention relates to a method which involves at least the following steps: a) obtaining a base oil composition which optionally contains one or more additives; b) obtaining a solution of one or more alkyl-substituted quinolines or oligomer derivatives thereof in a solvent, wherein the solvent is polyglycol; and c) adding the solution obtained at step b) to the base oil composition obtained at step a), at temperature ranging from 10 to 110°C. The present invention also relates to a lubricating composition and grease.
EFFECT: improved dispersion of alkyl-substituted quinolines when producing a lubricating composition, providing an alternative method of producing a lubricating composition.
12 cl, 2 ex, 1 tbl
SUBSTANCE: present invention relates to a lubricant composition for run-in and preservation of internal combustion engines, which contains mineral oil, oleic acid, ethylenediammonium tetraborate, sodium octadecylsulphonate, wherein in order to improve longevity of the oil film and preservation properties, the composition additionally contains piperidinium 3,5-dintrobenzoate, with the following ratio of components, wt %: oleic acid 0.1…1.1; ethylenediammonium tetraborate 0.1…0.5; sodium octadecylsulphonate 0.1…0.5; piperidinium 3,5-dintrobenzoate 0.4…0.5; mineral oil- up to 100.
EFFECT: obtaining a lubricant composition for simultaneous run-in and preservation of internal combustion engines.