1-substituted 3-(2-chloro-1h-indol-3-yl)-4-phenyl-1h-pyrrole-2,5-diones and use thereof in photochemical generation of stable fluorescent compounds and 2,8-substituted benzo[a]pyrrolo[3,4-c]carbazole-1,3-(2h,8h)-diones and use thereof as fluorophores

FIELD: chemistry.

SUBSTANCE: invention relates to novel 1-substituted 3-(2-chloro-1H-indol-3-yl)-4-phenyl-1H-pyrrole-2,5-diones of formula 1: , where R1 denotes H, C1-C6alkyl; R2 denotes compounds which, under the effect of visible light, form fluorescent 2,8-substituted benzo[a]pyrrolo[3,4-c]carbazole-1,3-(2H,8H)diones of formula II: , where R1 and R2 are as described above.

EFFECT: more effective use of the compounds.

10 cl, 2 tbl, 6 ex

 

The invention relates to new compounds, namely 1-substituted 3-(2-chloro-1H-indol-3-yl)-4-phenyl-1H-pyrrole-2,5-diones of General formula I:

where R1=H, C1-C6alkyl; R2=C1-C6alkyl, benzyl, phenyl.

Compound I under irradiation of visible light to generate a stable fluorescent substance 2,8-substituted benzo[a]pyrrolo[3,4-C]carbazole-1,3-(2H,8H)-diones II.

The invention relates also to the use of 3-(2-chloro-1H-indol-3-yl)-4-phenyl-1H-pyrrole-2,5-diones above General formula I as compounds able to photochemical generation of stable fluorophores that can be used, for example, in systems for storing information, in particular, as the photosensitive material components for three-dimensional recording and storing information.

The invention relates to new compounds, namely, 2,8-substituted benzo[a]pyrrolo[3,4-C]carbazole-1,3-(2H,8H)-diones of General formula II:

where R1=H, C1-C6alkyl; R2=C1-C6alkyl, benzyl, phenyl, except for the connection, where R1=N, a R2=CH3.

The invention relates also to the use of 2,8-substituted benzo[a]pyrrolo[3,4-C]carbazole-1,3-(2H,8H)-diones above General formula II as compounds with fluoresc what NTIA.

Most similar in structure to the compounds of General formula I are substituted 3-(7-ethyl-1H-indol-3-yl)-4-(1-methyl-1H-indol-7-yl)-1H-pyrrole-2,5-diones of the formula III:

Connections III /Margaret M. Paul, J.Org. Chem. 2004, 69, 2967-2975/ are used as the source for obtaining oxidizing photosynthesis substituted 3H-indolo-[6,7-a]pyrrolo[3,4-C]carbazole-4,6(5H,11N)-diones of General formula IV:

Most similar in structure to the compounds of General formula II above are substituted 3H-indolo-[6,7-a]pyrrolo[3,4-C]carbazole-4,6(5H,11N)-diones of General formula IV, which are inhibitors of the cyclin D1/CDK4 complex protein kinase that regulates cell division /Margaret M. Faul, J.Org. Chem. 2004, 69, 2967-2975/.

The technical result of the invention are new compounds in the range of 3-(1H-indol-3-yl)-1H-pyrrole-2,5-diones, showing new for this series of compounds properties to generate the action of light stable fluorescent substance.

The technical result is achieved by compounds of General formula I and their use as substances that form when the action of light stable fluorescent compounds II.

The technical result of the invention are new compounds in a series of benzo[a]pyrrolo[3,4-C]carbazole-1,3-(2H,8H)-diones, showing new for this series of compounds fluorescence their is TBA.

The technical result is achieved by compounds of General formula II and their use as fluorescent substances.

The invention satisfies the criterion of inventive step: we offer new compounds exhibit new properties in a series of structural analogues.

The method of obtaining the compounds of the first lies in the interaction of 3-(2-chloro-1H-indol-3-yl)-4-phenylfuro-2,5-diones V with aliphatic and aromatic amines:

where R1=H, C1-C6alkyl; R2=C1-C6alkyl, benzyl, phenyl.

The method of obtaining the compounds II is cyclization under the action of visible light 3-(1-alkyl-2-chloro-1H-indol-3-yl)-4-phenylfuro-2,5-diones of General formula I, where R1, R2have the above values, accompanied with evolution of hydrogen chloride:

Below are examples of the preparation of compounds I and II.

Example 1. 3-(2-Chloro-1-methyl-1H-indol-3-yl)-4-phenyl-1-propyl-1H-pyrrole-2,5-dione (R1=CH3, R2=n-propyl) (Ia).

To a solution of 0.1 g (0.3 mmole) of 3-(2-chloro-1-methyl-1H-indol-3-yl)-4-phenyl-furan-2,5-dione V (R1=CH3) in 5 ml of isopropyl alcohol was added dropwise 0.03 ml (0.45 mmole) of Propylamine. The mixture is refluxed for 1 hour and cooled. The precipitation is filtered off and crystallized from isopropyl sleep is the same. Yield 0.06 g (53%). Yellow crystals, TPL 129-130°C. IR spectrum, ν/cm-1: 687 (C-Cl), 1696 (C=O). An NMR spectrum1H (CDCl3, δ, ppm): 1.00 t (3H, CH3), 1.70-1.82 m (2H, CH2), 3.66 t (2H, CH2), 3.80 (3H, CH3), 7.00-7.38 m (7H, arene), 7.54-7.60 m (2N, arene). Found, %: C 69.69, H 5.01, N 5.80. C22H19ClN2O2. Calculated, %: C 69.72, H 5.05, N 7.39.

Example 2. 1-Benzyl-3-(2-chloro-1-methyl-1H-indol-3-yl)-4-phenyl-1H-pyrrole-2,5-dione (R1=CH3, R2=benzyl) (Ib).

Obtained as in (1A) of 3-(2-chloro-1-methyl-1H-indol-3-yl)-4-phenyl-furan-2,5-dione V (R1=CH3and benzylamine. Yield 0.07 g (55%). Yellow crystals, TPL 206-207°C. IR spectrum, ν/cm-1: 693 (C-Cl), 1700 (C=O). An NMR spectrum1H (CDCl3, δ, ppm): 3.78 (3H, CH3), 4.82 (2H, CH2), 7.00-7.26 m (2N, arene), 7.28-7.58 m (N, arene). Found, %: C 73.11, H 4.46, N 6.50. C26H19ClN2O2. Calculated, %: C 73.15, H 4.49, N 6.56.

Example 3. 3-(2-Chloro-1-methyl-1H-indol-3-yl)-1,4-diphenyl-1H-pyrrole-2,5-dione (R1=CH3, R2=phenyl) (Ic).

Obtained as in (Ia) of 3-(2-chloro-1-methyl-1H-indol-3-yl)-4-phenyl-furan-2,5-dione V (R1=CH3) and aniline. Yield 0.09 g (73%). Yellow crystals, TPL 199-200°C. IR spectrum, ν/cm-1: 691 (C-Cl), 1707 (C=O). An NMR spectrum1H (CDCl3, δ, ppm): 3.80-4.08 m (3H, CH3), 4.82 (2H, CH2), 7.02-7.28 m (3H, arene), 7.28-7.84 m (11N, arene). Found, %: C 72.70, H 4.11, N 6.75. C25H17ClN2O2. Calculated, %: C 72.3, H 4.15, N 6.78.

Example 4. 8-Methyl-2-propellent[a]pyrrolo[3,4-C]carbazole-1,3(2H,6H)-dione (R1=CH3, R2=n-propyl) (IIa).

A solution of 20 mg (0.053 mmole) of 3-(2-chloro-1-methyl-1H-indol-3-yl)-4-phenyl-1-propyl-1H-pyrrole-2,5-dione in 60 ml of a mixture of toluene - heptane (1:2) is irradiated in a quartz flask total light mercury lamps DRSH-250. The progress of the reaction is controlled by means of UV-spectroscopy. The precipitation is filtered off and recrystallized from butanol. Yield 17 mg (93.8%). Yellow crystals, TPL 240-241°C. IR spectrum, ν/cm-1: 1693 (C=O). An NMR spectrum1H (CDCl3, δ, ppm): 0.96 t (3H, CH3), 1.62-1.78 m (2H, CH2), 3.62 t (2H, CH2), 4.42 (3H, CH3), 7.30-7.48 m (1H, arene), 7.60-7.68 m (1H, arene), 7.80-7.98 m (3H, arene), 8.92-9.18 m (3H, arene). Found, %: C 77.13, H 5.28, N, 8.15. C23H18N2O2. Calculated, %: C 77.17, H 5.30, N 8.18.

Example 5. 2-Benzyl-8-methylbenzo[a]pyrrolo[3,4-C]carbazole-1,3(2H,6H)-dione (R1=CH3, R2=benzyl) (IIb).

Obtained as in (IIa) of 1-benzyl-3-(2-chloro-1-methyl-1H-indol-3-yl)-4-phenyl-1H-pyrrole-2,5-dione. Yield 16 mg (87.6%). Yellow crystals, TPL 279-280°C. IR spectrum, ν/cm-1: 1696 (C-O). An NMR spectrum1H (CDCl3, δ, ppm): 4.50 (3H, CH3), 4.94 (2H, CH2), 7.26-7.48 m (6N, arene), 7.60-7.70 m (1H, arene), 7.82-8.00 m (3H, arene), 8.96-9.18 m (3H, arene). Found, %: C 79.95, H 4.61, N 7.15. C26H18N2O2. Calculated, %: C 79.98, H 4.65, N7.17.

Example 6. 8-Methyl-2-phenylbenzo[and]Pyrrhus is lo[3,4-C]carbazole-1,3(2H,6H)-dione (R 1=CH3, R2=phenyl) (IIc).

Obtained as in (IIa) of 3-(2-chloro-1-methyl-1H-indol-3-yl)-1,4-di-phenyl-1H-pyrrole-2,5-dione. Yield 17 mg (93%). Yellow crystals, TPL 296-297°C. IR spectrum, ν/cm-1: 1704 (C=O). An NMR spectrum1H (CDCl3, δ, ppm): 4.50 (3H, CH3), 7.10-7.28 m (4H, arene), 7.40-7.70 m (3H, arene), 7.82-8.04 m (3H, arene), 8.88-9.24 m (3H, arene). Found, %: C 79.74, H 4.25, N, 7.41. C25H16N2O2. Calculated, %: 79.77, H 4.28, N 7.44.

The obtained compounds were investigated by standard methods, spectral absorption and spectral-fluorescent characteristics in toluene at 293K.

Electronic absorption spectra were recorded on a spectrophotometer "the Saga of 100 (Varian).

Irradiation of solutions of compounds I spent in a quartz cuvette (l=1 cm) by the light of 436 nm mercury lamp DRSH-250. The intensity of the incident light, measured by ferrioxalate potassium was 4.24·1015quantum·-1.

Values of the quantum yields of photoreactive was determined by the method described previously / Experimental methods of chemical kinetics, edited by Namamahala, Meglumine, Izd-vo MGU, Moscow, 1985, p 1661/.

Fluorescent measurements were carried out on an "Saga Eclipse (Varian). Values of the quantum outputs fluorescence was determined by the method of Parker - Rice /Sparker. Photoluminescence of solutions. Moscow, Mir, 1972, s/ using 3-m is oxybisethane in toluene (φ=0.1, λthe exposed.=365 nm) as a standard phosphor /Bmikeandvicki, Bambooteen. Organic phosphors. Moscow, Chemistry, 1984, s/.

In tables 1 and 2 list the results of studies of compounds Ia-C /examples 1-3/ and photoproduction IIa-C /examples 4-6/.

Table 1
Spectral absorption, spectral-fluorescence characteristics of the compounds Ia-C and quantum yields of the reaction of photocyclization
No.ConnectionAbsorptionFluorescenceQuantum yield of photo-cyclization, φ
λmaxnm (ε·10-3, l·mol-1·cm-1)λmax; nmQuantum yield, φ
Ia433 (7,03)5400,100,32
Ib435 (6,06) 5520,120,30
Ic440 (6,66)5600,050,46

Table 2
Spectral absorption, spectral-fluorescence characteristics of the compounds IIa-
No.ConnectionAbsorptionFluorescence
λmaxnm (ε·10-3,
l·mol-1·cm-1)
λmaxnmQuantum yield, φ
IIa428 (9,26)
441 (8,68)
4840,74
IIb430 (8,17)
443 (6,06)
4870,83
IIc 435 (8,50)4950,37

1. 1-Substituted 3-(2-chloro-1H-indol-3-yl)-4-phenyl-1H-pyrrole-2,5-diones of General formula I:
,
where R1=H1-C6alkyl; R2=C1-C6alkyl, benzyl, phenyl.

2. 1-Substituted 3-(2-chloro-1H-indol-3-yl)-4-phenyl-1H-pyrrole-2,5-dione according to claim 1, where R1=CH3, R2=n-propyl-3-(2-chloro-1H-indol-3-yl)-4-phenyl-1-propyl-1H-pyrrole-2,5-dione.

3. 1-Substituted 3-(2-chloro-1H-indol-3-yl)-4-phenyl-1H-pyrrole-2,5-dione according to claim 1, where R1=CH3, R2=benzene-1-benzyl-3-(2-chloro-1H-indol-3-yl)-4-phenyl-1 H-pyrrole-2,5-dione.

4. 1-Substituted 3-(2-chloro-1H-indol-3-yl)-4-phenyl-1H-pyrrole-2,5-dione according to claim 1, where R1=CH3; R2=phenyl-3-(2-chloro-1H-indol-3-yl)-1,4-diphenyl-1H-pyrrole-2,5-dione.

5. The use of 1-substituted 3-(2-chloro-1H-indol-3-yl)-4-phenyl-1H-pyrrole-2,5-diones of General formula I according to claim 1 as forming substances under the action of visible light fluorescent 2,8-substituted benzo[a]pyrrolo[3,4-C]carbazole-1,3-(2H,8H)dione of General formula II:
,
where R1=H, C1-C6alkyl; R2=C1-C6alkyl, benzyl, phenyl.

6. 2,8-Substituted benzo[a]pyrrolo[3,4-C]carbazole-1,3-(2H,8H)dione of General formula II:
,
where R1=H, C1- 6alkyl; R2=C1-C6alkyl, benzyl, phenyl, except for the connection, where R1=H, and R2=CH3.

7. Benzo[a]pyrrolo[3,4-C]carbazole-1,3-(2H,8H)dione according to claim 6, where R1=methyl, R2=propyl-8-methyl-2-propellent[and]pyrrolo[3,4-C]carbazole-1,3-(2H,8H)dione.

8. Benzo[a]pyrrolo[3,4-C]carbazole-1,3-(2H,8H)dione according to claim 6, where R1=methyl, R2=benzyl-2-benzyl-8-methylbenzo[and]pyrrolo[3,4-C]carbazole-1,3-(2H,8H)dione.

9. Benzo[a]pyrrolo[3,4-C]carbazole-1,3-(2H,8H)dione according to claim 6, where R1=methyl, R2=phenyl-8-methyl-2-phenylbenzo[and]pyrrolo[3,4-C]carbazole-1,3-(2H,8H)dione.

10. The use of 2,8-substituted benzo[a]pyrrolo[3,4-C]carbazole-1,3-(2H,8H)-diones of General formula II, where R1=H, C1-C6alkyl; R2=C1-C6alkyl, benzyl, phenyl as fluorophores.



 

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12 cl, 3 tbl, 2 ex, 1 dwg

FIELD: chemistry.

SUBSTANCE: invention relates to pyrrolotriazines of formula (I) , where R1 is selected from a group which includes phenyl, naphthyl, benzyl and heteroaryl, which denotes a mono- or bicyclic radical containing 5-10 ring atoms and up to 2 heteroatoms selected from a group consisting of nitrogen, oxygen and sulphur, at least one ring of which is aromatic, where, if necessary, phenyl and heteroaryl may be substituted with 0, 1 or 2 substitutes independently selected from a group consisting of -(C1-C4)alkyl, where -(C1-C4)alkyl can be substituted with 0, 1, 2 or 3 halogens, 0 or 1 pyrrolidine, -(C1-C3)alkoxy group, where, if necessary, the (C1-C3)alkoxy group may be substituted with a (C1-C3)alkylamino group, halogen, trifluoromethyl, trifluoromethoxy group, phenyl, if necessary substituted with 1 or 2 halogens, - , where X denotes O, nitro group, - (C1-C3)alkylthio group, trifluoromethylthio group, - (C1-C3)alkylcarbonyl, - (C1-C6)alkoxycarbonyl, and a phenoxy group, and where the benzyl can be substituted with 0, 1, 2 or 3 groups selected from a group which includes halogen; R2 is selected from a group consisting of hydrogen, halogen; R3 is selected from a group consisting of carboxyl, - (C1-C6)alkylcarbonyl, - (C3-C6)cycloalkylcarbonyl, - (C1-C6)alkoxycarbonyl, if necessary substituted with 0, 1, 2 or 3 groups selected from a group which includes amino group and (C1-C6)alkoxycarbonyl; aminocarbonyl, -(C1-C6)alkylaminocarbonyl, where (C1-C6)alkylaminocarbonyl which, if necessary, can be substituted with 0, 1, 2 or 3 substitutes independently selected from a group consisting of (C3-C6)cycloalkyl, halogen, amino group, (C1-C6)alkylamino group, hydroxy group, (C1-C6)alkoxy group, (C1-C6))alkoxycarbonyl, (C1-C6)alkylthio group, (C1-C6)alkoxycarbonylamino group,and where, if necessary, (C1-C6)alkylaminocarbonyl may be substituted with 0 or 1 heterocyclyl, which denotes a monocyclic, non-aromatic radical containing 5-8 ring atoms and up to 2 heteroatoms selected from nitrogen and oxygen, where, if necessary, the hetecyclyl may be substituted with 0 or 1 (C1-C6)alkyl, heterocyclylcarbonyl, if necessary substituted with 0 or 1 (C1-C6)alkylamino group, cycloalkyl or (C1-C6)alkyl,where, if necessary, (C1-C6)alkyl may be substituted with 0 or 1 (C1-C6)alkylamino group, and where heterocyclyl denotes a monocyclic, non-aromatic radical containing 5-8 ring atoms and up to 2 heteroatoms selected from nitrogen and oxygen, -(C1-C6)alkyl if necessary substituted with 0, 1 or 2 substitutes independently selected from a group consisting of a) hydroxyl, b) (C1-C6)alkylamino group, where (C1-C6)alkylamino group may be substituted with 0, 1 or 3 substitutes independently selected from a group consisting of halogen, alkylamino group, methoxy group, methylthio group and methylsulphonyl, c) phenylamino group, where the phenylamino group may be substituted with 0, 1 or 2 substitutes independently selected from a group consisting of (C1-C6)alkoxy group and trifluoromethyl, d) heterocyclyl, where heterocyclyl denotes a monocyclic, non-aromatic radical containing 5-8 ring atoms and up to 2 heteroatoms selected from nitrogen and oxygen, and where the heterocyclyl may be substituted with 0 or 1 (C1-C6)alkyl, where (C1-C6)alkyl may be substituted with 0 or 1 methoxy groups or pyridyls, e) imidazolyl, f) pyridylamino group, g) (C1-C3)alkoxy group, if necessary substituted with fluorine or piperidine,where, if necessary, the piperidine may be substituted with 0 or 1 (C1-C6)alkyl, h) (C1-C3)alkoxy(C2-C3)alkoxy group, and i) (C1-C6)alkoxycarbonyl, j) (C3-C6)cycloalkyl, k) cyano group, - (C3-C6)cycloalkylaminocarbonyl, cyano group, heteroaryl, where heteroaryl denotes a monocyclic radical containing 5-6 ring atoms and up to 3 heteroatoms selected from a group consisting of nitrogen and oxygen, the ring of which is aromatic, where the heteroaryl may be substituted with 0, 1 or 2 groups independently selected from a group consisting of q) (C1-C6)alkyl, where the (C1-C6)alkyl may be substituted with 0 or 1 morpholine or 0 or 1 hydroxy group, r) (C1-C6)alkoxycarbonyl, thiophene carbonyl, and R4 is selected from a group consisting of hydrogen; to a pharmaceutically acceptable salt thereof. The invention also pertains to methods of obtaining said compounds.

EFFECT: obtaining novel compounds which can be used in medicine for preventing or treating hyper-proliferative disorders and diseases associated with angiogenesis.

5 cl, 313 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a crystalline form of (R)-6-cyclopentyl-6-(2-(2,6-diethylpyridin-4-yl)ethyl)-3-((5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl)-4-hydroxy-5,6-dihydropyran-2-one, which exhibits characteristic peaks on an X-ray powder diffraction pattern expressed in two-theta degrees, selected from approximately 7.1, approximately 12.1 and approximately 16.1; or approximately 7.1, approximately 12.1 and approximately 17.5; or approximately 7.1, approximately 12.1 and approximately 23.5; or approximately 12.1, approximately 16.1 and approximately 17.5; or approximately 12.1, approximately 16.1 and approximately 23.5; or approximately 16.1, approximately 17.5 and approximately 23.5; or approximately 7.1, approximately 17.5 and approximately 23.5; or approximately 7.1, approximately 12.1 and approximately 23.5; or approximately 7.1, approximately 16.1 and approximately 23.5, and to a pharmaceutical composition based on said compound, which can be used in medicine to prepare a medicinal agent which acts on the hepatitis C virus (HCV) in HCV-infected mammals.

EFFECT: improved properties of derivatives.

12 cl, 1 tbl, 3 dwg, 11 ex

FIELD: chemistry.

SUBSTANCE: invention relates to novel substituted tetracyclic derivatives of tetrahydropyran, pyrrolidine and tetrahydrothiophene of general formula (I), their pharmaceutically acceptable addition salts, their stereochemically isomeric forms, their N-oxide forms, in which all substitutes are defined in claim 1 of the formula of invention. These compounds have binding affinity to serotonin receptors, particularly 5-HT2A and 5-HT2C receptors, and to dopamine receptors particularly D2 dopamine receptors, and have norepiniphrine reuptake inhibition properties. The invention also relates to a pharmaceutical composition containing said compounds, method of preparing said composition and use of said compounds as medicinal agents, particularly for preventing and/or treating several psychiatric and neurological disorders.

EFFECT: new compounds have useful biological properties.

12 cl, 3 tbl, 49 ex

FIELD: chemistry.

SUBSTANCE: invention relates to novel substituted 2-alkylamino-3-sulfonyl-pyrazolo[1,5-a]pyrimidines, their pharmaceutically acceptable salts and/or hydrates which have serotonin 5-HT6 receptor antagonist properties and can be used in treating or preventing development of various central nervous system diseases, whose pathogenesis is related to 5-HT6 receptors, particularly Alzheimer's disease, Parkinson's disease, Huntington disease, schizophrenia, other neurodegenerative diseases, cognitive and anxiety disorders and obesity. In general formula (I):

R1 and R3 independently denote optionally identical C1-C3alkyl, R2 is a -(CH2)nX group or R1 and R3 independently denote different substitutes selected from C1-C3 alkyl or a -(CH2)nX group, and R2 is a hydrogen atom or C1-C3alkyl; R4 is C1-C3alkyl; Ri5 is a hydrogen atom, one or two identical or different halogen atoms, C1-C3alkyl; i is equal to 0, 1 or 2; n is equal to 0, 1, 2 or 3; X is a carboxyl CO2H, C1-C3alkyloxycarbonyl, aminocarbonyl CONR6R7 or a NR6R7 amino group; R6 and R7 denote optionally identical hydrogen atom, optionally substituted C1-C3 alkyl, C3-C7cycloalkyl or an optionally substituted 5-7-member azaheterocyclyl containing 1-2 nitrogen atoms in the ring, where the substitutes are selected from C1-C3alkyl; or R6 and R7 together with the nitrogen atom to which they are bonded form an optionally substituted 5-6-member azaheterocyclyl containing 1-2 nitrogen atoms in the ring, where the substitutes are selected from C1-C3alkyl.

EFFECT: obtaining new biologically active compounds.

26 cl, 12 dwg, 4 tbl, 14 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method for synthesis of novel derivatives of benzo[7,8]azonino[5,4-b]indoles, 7,9-etheno-azecino[5,4-b]indoles and 7,9-ethano-azecino[5,4-b]indoles with general structural formulae: , , , I, IV, VII X=H,Y=CO2Me; II, V, VIII X=H, Y=COMe; III, VI, IX X=Y=CO2Me, which have proved to be cytostatic and cytotoxic compounds. The method involves dissolving 3,8,13,13b-tetrahydro-5H-benzo[1,2]indolysino[8,7-b]indole, ethyl eburnamenine-14-carboxylate or methyl (3-α, 14-β, 16α)-14-hydroxy-14,15-dihydro eburnamenine -14-carboxylate in methanol and then reaction with excess dimethyl acetylenedicarboxylate (ADCX) or methyl propiolate or acetyl acetylene, while stirring at +40-+50°C, with subsequent removal of the solvent and grinding the residue in hexane or a mixture of hexane with ethylacetate (ether) or purified using column chromatography on aluminium oxide.

EFFECT: design of an efficient method of obtaining hazardous compounds.

9 ex

FIELD: chemistry.

SUBSTANCE: invention describes novel compounds of general formula: , where R1 - C1-C6alkyl, C1-C6alkoxy, halogen, CN, C(O)NH2 or OCH2CH2OCH3; R2-C1-C6alkyl, possibly substituted with halogen, a halogen, C1-C6alkoxy, phenyl, N(R6)2, (OCH2CH2)nOCH3, O(CH2)mNR7R8, where n equals 1 or 2; m equals 2 or 3; R6 -R7 -C1C6alkyl, and R8 -OCH2CH2OCH3; or R7 and R8 together with the nitrogen atom to which they are bonded form a 6-member heterocycle which additionally contains one oxygen atom or one nitrogen atom, which in the latter case is substituted with C1-C4alkyl; or R1 and R2 together form a 5-member heterocyclic ring system containing two oxygen atoms as heteroatoms; R3 - hydrogen or C1-C6alkyl; R4 - hydrogen, halogen or C1-C6alkoxy; or pharmaceutically acceptable salts thereof, and pharmaceutical compositions containing these compounds.

EFFECT: obtaining novel compounds with kinase inhibiting properties, particularly CDK2, or angiogenesis inhibiting properties and can be used in treating malignant growths, particularly in mammary glands, large intestines, lungs and prostate glands.

60 cl, 7 tbl, 101 ex

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of formula (I): or pharmaceutically acceptable salts thereof, where X is CH; R1 is phenyl or a 6-member heteroaryl which contains 1 or 2 nitrogen atoms as heteroatoms, independently and optionally substituted with up to five groups J; R2 and R3 each independently represents hydrogen, halogen, -V-R or -V-Ra; R5 is R; R is H or an optionally substituted C1-6aliphatic group, where the substitutes are selected from -OR0, phenyl, substituted R0, -N(R0)2; where each independent R0 is selected from hydrogen, halogen, C1-6aliphatic group; Ra is morpholine, V is a bond or Q; Q is -NR5-; each J group independently represents a halogen, -N(R5)2. The invention also relates to a pharmaceutical composition with protein kinase inhibiting properties, and to methods of inhibiting Aurora A protein kinase using the said compounds.

EFFECT: obtaining novel compounds and pharmaceutical compositions based on the said compounds, which can be used in medicine to treat or alleviating a proliferative disorder, such as cancer, in a patient.

25 cl, 2 tbl, 2 ex

FIELD: chemistry.

SUBSTANCE: present invention relates to pyrido[1,2-a]benzimidazole derivatives of general formula I, where R=alkyl; R1=alkyl, aryl; R2=alkyl. The invention also relates to a method of producing formula I compounds.

EFFECT: novel to pyrido[1,2-a]benzimidazole derivatives with antibacterial activity are obtained.

2 cl, 2 tbl

FIELD: medicine.

SUBSTANCE: invention refers to 3 - (2-methoxy-4-pyrazol-1-ilfenil) -2,5-dimethyl-7-(3-methylpyridine-2-yl) pyrazolo [1.5-a] pyrimidine or its pharmaceutically acceptable salts, solvate, stereoisomer, having the following structural formula, which are antagonists of CRF-receptors and can be used in treatment of various disorders that cause hypersecretion of CRF in warm-blooded animals, such as at the sudden attack. Also the invention refers to intermediate compounds, pharmaceutical compositions on the basis of this compound and method of treating disorder causing hypersecretion of CRF in mammals.

EFFECT: improvement of composition.

15 cl, 14 tbl, 28 ex

FIELD: chemistry.

SUBSTANCE: invention describes tetrahydrates of pharmaceutically acceptable calcium and magnesium salts of ibersartan in crystalline form and preparation thereof in an aqueous medium of a sodium salt.

EFFECT: improved method.

4 cl, 2 dwg, 2 ex

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