The method of obtaining chiral compounds, 3-(azidomethyl)-5 - methylhexanoic acid, or its fenilmetilovy, or 1,1 - dimethylethylene esters

 

(57) Abstract:

The invention relates to methods of preparing compounds of the formula I H2NCHR3-CR1R2-CH2COOH, where R1- straight or branched alkyl, C1-C6C6H5,

cycloalkyl C3-C6, R2- H or CH3, R3- H, CH3or carboxyl, provided that when each of R2and R3- H, R1distinguished from CH3interacting compounds , where R is benzyl or 1,1-dimethylethyl, which is then hydrolized and restore. 2 S. p. f-crystals, 6 PL.

 

Same patents:

The invention relates to a new method of obtaining gabentin-1- (aminomethyl)cyclohexadecane formula(I) which are used in medicine as anti-convulsants

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to novel 1,2,3-tris-[(ammonio)methylcarbonyloxypoly(alkyleneoxy)]-propane trichlorides of the general formula:

wherein at -X+ as -N+R1RR, R1 = R2 mean hydrogen atom (H), R3 means aliphatic hydrocarbon radical comprising 10-16 carbon atoms, a + c + e (the general degree of oxypropylation) = 49,b + d + f (the general degree of oxyethylation) = 0; at -X+ as -N+R1R2R3, R1 = R2 mean H, R3 means aliphatic hydrocarbon radical comprising 10-16 carbon atoms, a + c + e = 55, b + d + f = 0; at -X+ as -N+R1R2R3, R1 = R2 mean H, R3 means aliphatic hydrocarbon radical comprising 10-16 carbon atoms, a + c + e = 80, b + d + f = 24; at -X+ as -N+R1R2R3, R1 = R2 mean H, R3 means aliphatic hydrocarbon radical comprising 10-16 carbon atoms, a + c + e = 90, b + d + f = 27; at -X+ as -N+R1R2R3, R1 = R2 means H, R3 means phenyl, a + c + e = 80, b + d + f = 24; at -X+ as -N+R1R2R3, R1 = R2 mean H, R3 means phenyl, a + c + e = 90, b + d + f = 27; at -X+ as , a + c + e = 80, b + d + f = 24; at -X+ as , a + c + e = 90, b + d + f =27. Also, invention relates to a method for synthesis of these compounds. Method involves interaction of 1,2,3-tris-[hydroxypoly(alkyleneoxy)]-propane of the formula:

wherein a + c + e = 49-90, b + d + f = 0-27 with monochloroacetic acid in the presence of acidic catalyst, in boiling organic solvent medium with azeotropic removal of water formed and the following treatment of synthesized reaction product in polar solvent medium at heating with amino-compounds of the formula: NR1R2R3 wherein R1 = R2 mean H, R3 means aliphatic hydrocarbon radical comprising 10-16 carbon atoms, phenyl, or morpholine of the formula:

in the following mole ratios of reagents - propane hydroxyl derivative : monochloroacetic acid : amino-compound or morpholine = 1:(3.0-3.2):(3.0-3.2), respectively. New compounds show the bactericidal and fungicide activity and properties of demulsifying agents for petroleum emulsions.

EFFECT: improved method of synthesis, valuable properties of compounds.

7 cl, 3 tbl, 8 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to novel 1,2,3-tris-[(ammonio)methylcarbonyloxypoly(alkyleneoxy)]propane trichlorides of the formula: wherein: if R1 = R2 = R3 mean -CH2CH2OH then a + c + e (the total degree of oxypropylation) = 49, b + d + f (the total degree of oxyethylation) = 9; if R1 = R2 = R3 mean -CH2CH2OH then a + c + e = 55, b + d + f = 10; if R1 = R2 = R3 mean -CH2CH2OH then a + c + e = 66, b + d + f = 15; if R1 = R = R3 -CH2CH2OH then a + c + e = 76, b + d + f = 18; if R1 = R2 mean hydrogen atom (H); R3 means aliphatic hydrocarbon radical comprising 10-16 carbon atoms then a + c + e = 76, b + d + f =18; if R1 = R2 mean H; R3 means aliphatic hydrocarbon radical comprising 17-20 carbon atoms then a + c + e = 49, b + d + f = 0; if R1 = R2 mean H; R3 means aliphatic hydrocarbon radical comprising 17-20 carbon atoms then a + c + e = 55, b + d + f = 0; if R = R means H; R3 means then a + c + e = 49, b + d + f = 9; if R1 = R2 mean H; R3 means then a + c + e = 55, b + d + f =10, and to a method for their synthesis. Method involves interaction 1,2,3-tris-[hydroxypoly(alkyleneoxy)propanes of the formula: wherein a + c + e = 49-76, b + d + f = 0-18 with monochloroacetic acid in the presence of acidic catalyst, in boiling organic solvent medium and azeotropic removal of formed water and the following treatment of the synthesized reaction product at heating with amino-compounds of the formula: R1R2N wherein R1 = R2 mean -H, -CH2CH2OH; R3 means -CH2CH2OH, aliphatic radical comprising 10-16 or 17-20 carbon atoms, and in the molar ratio of reagents - propane hydroxyl derivatives : monochloroacetic acid : amino-compounds = 1:(3.0-3.2):(3.0-3.2), respectively. Novel compounds possess properties of emulsifiers of aqueous-mazut emulsions.

EFFECT: improved method of synthesis, valuable technical properties of compounds.

6 cl, 1 tbl, 10 ex

FIELD: chemistry.

SUBSTANCE: present invention relates to methods for synthesis of compounds of formula (A), where R1 denotes halogen, C1-C6halogenalkyl, C1-C6alkoxy(C1-C6)alkyloxy or C1-C6alkoxy(C1-C6)alkyl; R2 denotes halogen, C1-C4alkyl or C1-C4alkoxy; R3 and R4 independently denote a branched C3-C6alkyl; and R5 denotes C3-C12cycloalkyl, C1-C6alkyl, C1-C6hydroxyalkyl, C1-C6alkoxy(C1-C6)alkyl, C1-C6alkanoyloxy(C1-C6)alkyl, C1-C6aminoalkyl, C1-C6alkylamino(C1-C6)alkyl, C1-C6dialkylamino(C1-C6)alkyl, C1-C6alkanoylamino(C1-C6)alkyl, HO(O)C-(C1-C6)alkyl, C1-C6alkyl-O-(O)C-(C1-C6)alkyl, H2N-C(O)-(C1-C6)alkyl, C1-C6alkyl-HNC(O)-(C1-C6)alkyl or (C1-C6alkyl)2N-C(O)-(C1-C6)alkyl, or their pharmaceutically acceptable salts which have renin inhibiting activity, as well as to basic intermediate compounds obtained during steps for synthesis of the desired compounds and to methods for synthesis of said intermediate compounds.

EFFECT: alternative synthesis method.

43 cl, 8 dwg, 11 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to a new method for preparing aminophenoxyphthalic acids that are monomers of type AB used for preparing polyimides. Aminophenoxyphthalic acids of the general formula (I) are given in the invention description wherein Y means trivalent radical taken among radicals row of the general chemical structure (II) or (III) given in the invention description wherein R means hydrogen atom (H), oxyphenyl, N-morpholinyl radicals. Method for their preparing involves two stages: in the first stage method involves carrying out the process of interaction of nitrophthalonitrile of the general formula (IV) given in the invention description wherein R has above indicated values with 3- or 4-acetamidophenol of the general formula (V) given in the invention description in the presence of alkaline metal carbonate in amide solvent medium. Then as alkaline metal carbonate method involves using potassium carbonate mainly and dimethylformamide or dimethylacetamide aqueous solutions are used as an amide solvent. Alkaline hydrolysis is carried out in an aqueous-methanol potassium hydroxide (KOH) solution. Prepared aminophenoxyphthalic acid is isolated as a precipitate by acidification of the reaction mass with acetic acid mainly up to pH 4-5. Aminophenoxyphthalic acids are monomers used for synthesis of polyimides comprising at least one repeated link taken among links row of the general formula (VI) given in the invention description wherein Y has above indicated values. Invention provides preparing new aminophenoxyphthalic acids, for example, oxyphenyl- or N-morpholinyl-substituted acids. Applying these compounds allows expanding possibility for preparing polyimides having substitutes and comprising hinged fragments in the main chain, in particular, oxygen atoms that as one can expect must enhance the chain flexibility and therefore to promote appearance of thermoplasticity property.

EFFECT: improved preparing method, improved and valuable properties of compounds.

5 cl, 1 sch, 6 ex

FIELD: analytical chemistry of organic compounds useful in determination of protein fermentation, analysis of waste waters from pharmaceutical an food processing industries.

SUBSTANCE: claimed method includes graining agent in form of crystal lithium sulfate in amount of 20 mass % is added to aqueous solution of aspartic acid and glutamine. Solution is stirred, and mixture of hydrophilic solvents containing 20 % mass of isopropanol, 20 % mass of acetone, and 60 % mass of ethyl acetate is added in solution/solvent mixture volume ratio of 1:10. Obtained mixture is extracted, extract is separated and content of aspartic acid and glutamine is detected on the base of differential curve of potentiometric titration with KOH solution in anhydrous ethanol. Aspartic acid or glutamine content is evaluated on the base of recovery degree thereof (R, %), calculated as R = D.100/D+r, wherein D is distribution coefficient of aspartic acid or glutamine between solvent mixture and solution; r is ratio of equilibrium volumes of aqueous and organic phases.

EFFECT: improver method for separate determination of aspartic acid and glutamine due to application of three-component mixture of hydrophilic solvents.

6 ex, 1 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to novel compounds of formula (I) which can be used in diagnosis of tumorous diseases. In formula (I) , A is OH, C1-C5 alkoxy, N(C1-C5 alkyl)2, NH2; G is OH, O-C1-C5 alkyl; R1 and R2 independently denote H, 18F, 18F-C1-C5 alkoxy, 18F-C1-C5 alkyl, provided that if one of the substitutes R1 and R2 contain an 18F isotope, the other does not. The invention also relates to compounds of formulae and which are used in synthesis of formula (I) compounds, as well as to use of compounds of formula (IV) in synthesis of compounds of formula (I) or (II).

EFFECT: obtaining novel compounds which can be used in diagnosis of tumorous diseases.

29 cl, 4 ex, 8 tbl, 4 dwg

FIELD: chemistry.

SUBSTANCE: invention relates to a product of reaction of triamine and dialkyl maleate and/or dialkyl fumarate, with viscosity less than 2000 cP. The triamine has the following structure: , where all n are identical or different and each is an integer. A coating composition and a substrate (versions) are also disclosed.

EFFECT: product is used as a hardener for producing polyurea coatings.

27 cl, 7 tbl, 25 ex

FIELD: chemistry.

SUBSTANCE: disclosed is a method of producing lipodipeptides based on L-glutamic acid or L-glutamine and L-ornithine, L-lysine or L-arginine. L-glutamic acid or L-glutamine derivatives esterified with fatty alcohol residues are obtained by fusing an amino acid with a corresponding alcohol in the presence of a strongly acidic ion-exchange resin in H+ form. Amino groups of L-ornithine, L-lysine or L-arginine are protected and then activated with carboxyl groups. Further, a reaction takes place between esterified derivatives of L-glutamic acid or L-glutamine and the protected derivatives of L-ornithine, L-lysine or L-arginine to form lipodipeptides. The protective groups are then removed.

EFFECT: invention simplifies the process at the esterification step, reduces reaction temperature and reaction time to 2 hours.

3 ex

FIELD: chemistry.

SUBSTANCE: invention relates to chemistry and specifically to N,N-diallyl aspartic acid of formula , which can be used as a starting compound (monomer) for producing novel polyelectrolytes with a controlled acid-base and hydrophilic-hydrophobic balance, which are used as flocculants, coagulants, etc.

EFFECT: invention also relates to a method of producing N,N-diallyl aspartic acid by reacting a sodium salt of α-aspartic acid in a water-alcohol solution with allyl chloride.

2 cl, 1 dwg, 2 tbl, 7 ex

FIELD: chemistry.

SUBSTANCE: invention relates to method of obtaining iodinated anilines, in particular, it relates to method, which includes direct iodination of 3,5-disubstituted anilines to respective 3,5-disubstituted-2,4,6-tri-iodanilines, which are applicable as intermediate products for synthesis of contrast media for X-rays and for preparation of contrast media. Method of obtaining 5-amino-2,4,6-tri-iodisophthalic acid of formula (II) includes iodination of 5-aminoisophthalic acid of formula (I) carried out in polar solvent and in acidic conditions, or its salt with molecular iodine and in presence of iodic acid, where molar ratio between molecular iodine and 5- aminoisophthalic substrate (I) constitutes from 1 to 1.5, and molar ratio of iodine to iodic acid constitutes from 1:0.5 to 1:1, and equivalent ratio between 5- aminoisophthalic substrate (I) and iodinating component, considered in form of the sum of I2 and HIO3, constitutes at least 1:3. Invention also relates to methods of obtaining compounds of formula (III) in which R and R', are similar or different from each other, stand for group, selected from carboxy (-COOH), carboxy ester (-COOR1) and carboxamido (-CONH2, -CONHR1 or -CONR2R3), where R1, R2 and R3, are similar or different from each other, represent linear or branched C1-C4alkyl group optionally substituted by one or several hydroxyl groups, and R4 and R5 are similar or different from each other, represent hydrogen or linear or branched C1-C6alkyl group, optionally substituted by one or several hydroxyl or C1-C6alkoxygroups.

EFFECT: increase of method efficiency.

15 cl, 8 dwg, 9 ex, 1 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to a zinc or copper salt of general formula (II) which is used as a biocide, wherein M is Zn or Cu, R1 is selected from a group which includes hydrogen and methyl, R2 is substituted C1-C5 alkyl, m=0-5, n=0-2, m+n=1-5. The copper and zinc (II) salts have high biocidal activity and a wide range of action on biological objects. Said salts can be used in disinfectant compositions for various purposes, coating compositions, paper and wood treatment compositions, polymer compositions with high fungal resistance, as well as in many methods of preventing negative effect on biological objects, particularly shellfish, on organisms and materials.

EFFECT: improved method.

2 cl, 28 ex, 4 tbl

FIELD: chemistry.

SUBSTANCE: invention refers to a method for producing a mixture of aspartic acid diethoxysuccinate and an amino acid derivative of general formula , which can find application as a chelating agent. In formula I, n is equal to 1-10, m is equal to 0 or 1, whereas R represents a hydrogen atom or an alkali or alkali earth metal ion. The method involves carrying out a reaction of maleate and diethanolamine in the alkali medium in the presence of a lanthanide catalyst element to form aspartic acid diethoxysuccinate. That is followed by adding aspartic acid, which reacts with unreacted maleate to form iminodisuccinic acid, i.e. an amino acid derivative of formula I, wherein m is equal to 0, or adding a diamine derivative of general formula NH2(CH2)nNH2 II, wherein n is such as described above, which reacts to unreacted maleate to form the amino acid derivative of formula I, wherein m is equal to 1, whereas n is such as specified above.

EFFECT: method enables producing the mixtures of chelating agents with the use of unreacted maleate from the process of producing aspartic acid diethoxysuccinate that makes the presented method more cost-efficient.

11 cl, 2 tbl, 2 ex

FIELD: chemistry.

SUBSTANCE: present invention relates to a method of regenerating a lanthanide catalyst from synthesis of diethoxysuccinate of aspartic acid. The method includes contacting a carbonate source with a solution containing lanthanide ions, formed during said synthesis, and a chelating agent, different from diethoxysuccinate of aspartic acid, for precipitation of a lanthanide carbonate followed by separation of the precipitated lanthanide carbonate from the solution, wherein said chelating agent is iminodisuccinic acid or ethylenediamine disuccinic acid. The invention also relates to a method of producing diethoxysuccinate of aspartic acid, which includes reacting diethanolamine with a maleate in alkaline conditions in the presence of a lanthanide catalyst.

EFFECT: improved regeneration of a lanthanide catalyst for synthesis of diethoxysuccinate of aspartic acid.

12 cl, 4 dwg, 4 tbl, 4 ex

FIELD: chemistry.

SUBSTANCE: invention refers to pharmaceutical chemistry, namely to new biologically active substances (BAS) and to their properties, namely to kreatine derivatives of general formula: NH=C(NH2)-N(CH3)-CH2-CO-NH-R∗X, where R is aminoacid residual of aliphatic, aromatic or heteroaromatic amino acid or its derivative, representing pharmaceutically acceptable salts of amino acids, esters of amino acids, amides of amino acids or peptides; X is low-molecular organic or mineral acid, or water. New substances are produced by interaction of guanydilic agents and sarcosine amides in polar organic solvents at temperature 50°C and less.

EFFECT: new compounds can be used as a neuroprotective agent.

3 cl, 10 ex, 6 tbl

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to a compound of general formula (I), in the form of optical isomers or their mixtures, and its pharmaceutically acceptable salt, which show activity as α2δ ligand and affinity to a subunit of α2δ potential-dependent calcium channels. In formula each R1, R2, R2', R4, R5, R8 and R8' independently represents hydrogen atom, halogen atom or C1-C6 alkyl group; each R6 and R7 independently represents hydrogen atom or C1-C6 alkyl group; or R2 and R2' together with carbon atom whereto attached form C3-C7 cycloalkyl group; R3 represents hydrogen atom, C1-C6 alkyl group, C1-C6 alkylhalogenide group, C1-C6 alkoxy-C1-C6 alkyl group, C2-C6 alkenyl group, C2-C6 alkynyl group, C1-C6 alkylsulphanyl-C1-C6 alkyl group, C2-C7 acyloxy-C1-C6 alkyl group or C3-C7 cycloalkyl group.

EFFECT: preparing the pharmaceutical composition for treating and/or preventing pain.

25 cl, 19 tbl, 43 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to new compounds of formula (I) or pharmaceutically acceptable salts thereof having mu-opioid receptor antagonist activity. In formula (I), R1 means -ORa or -C(O)NRbRc; R2, R3 and R4 mean, each independently, C1-3alkyl; R5 is specified in C1-6alkyl, cyclohexyl, -(CH2)1-3-cyclohexyl and -(CH2)1-3-phenyl; Ra, Rb and Rc mean, each independently, hydrogen; and R6 means hydrogen or C1-3alkyl; and substitutes in the starred chiral centres are found in a trans configuration. The invention also refers to a method for preparing compounds of formula (I), to intermediate compounds used in the synthesis of the compounds of formula (1) and a method for preparing them. Furthermore, the invention refers to a pharmaceutical composition comprising the compounds of formula (I), and to the use of such compounds for treating the diseases or conditions associated with mu-opioid receptor activity.

EFFECT: new pharmaceutical composition is presented.

25 cl, 19 ex

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