RU2763730C1 - Application of 3-(4-chlorobenzoyl)-2-hydroxy-3-(2-oxo-indolin-3-yl)-1h-benzo[b]pyrrolo[1,2-d][1,4]-oxazin-1,4(3аh)-dione as an agent with antimicrobial activity - Google Patents
Application of 3-(4-chlorobenzoyl)-2-hydroxy-3-(2-oxo-indolin-3-yl)-1h-benzo[b]pyrrolo[1,2-d][1,4]-oxazin-1,4(3аh)-dione as an agent with antimicrobial activity Download PDFInfo
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- 230000000845 anti-microbial effect Effects 0.000 title claims abstract description 11
- IPDBDWRIMXJQHZ-UHFFFAOYSA-N ClC1=CC=C(C(=O)C2=C(C(N3C2(C(OC2=C3C=CC=C2)=O)C2C(NC3=CC=CC=C23)=O)=O)O)C=C1 Chemical class ClC1=CC=C(C(=O)C2=C(C(N3C2(C(OC2=C3C=CC=C2)=O)C2C(NC3=CC=CC=C23)=O)=O)O)C=C1 IPDBDWRIMXJQHZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 13
- 239000000126 substance Substances 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- HBENZIXOGRCSQN-VQWWACLZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylpentan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol Chemical compound N1([C@@H]2CC=3C4=C(C(=CC=3)O)O[C@H]3[C@@]5(OC)CC[C@@]2([C@@]43CC1)C[C@@H]5[C@](C)(O)C(C)(C)CC)CC1CC1 HBENZIXOGRCSQN-VQWWACLZSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CYSSQKDNQDPPBI-UHFFFAOYSA-N 3-(4-chlorobenzoyl)pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-trione Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=C2C(=O)OC3=CC=CC=C3N2C(=O)C1=O CYSSQKDNQDPPBI-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000005935 nucleophilic addition reaction Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- VRUUPCFUXQAQAQ-UHFFFAOYSA-N pyrrolo[2,3-h][1,2]benzoxazine-3,4,5-trione Chemical class O1NC(C(C2=C1C=1C(=CC2=O)N=CC=1)=O)=O VRUUPCFUXQAQAQ-UHFFFAOYSA-N 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5365—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
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- Health & Medical Sciences (AREA)
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- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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Abstract
Description
Изобретение относится к области органической химии, а именно к применению индивидуальных соединений класса 3-ароил-2-гидрокси-3а-(2-оксо-индолин-3-ил)-1H-бензо[b]пирроло[1,2-d][1,4]-оксазин-1,4(3aH)-дионов в качестве средств, обладающих противомикробной активностью, которые могут быть использованы в качестве исходных продуктов для синтеза новых гетероциклических систем и в фармакологии.The invention relates to the field of organic chemistry, namely the use of individual compounds of the class 3-aroyl-2-hydroxy-3a-(2-oxo-indolin-3-yl)-1H-benzo[b]pyrrolo[1,2-d] [1,4]-oxazine-1,4(3aH)-diones as agents with antimicrobial activity, which can be used as starting products for the synthesis of new heterocyclic systems and in pharmacology.
Заявленное соединение 3-(4-хлорбензоил)-2-гидрокси-3а-(2-оксо-индолин-3-ил)-1Н-бензо[b]пирроло[1,2-d][1,4]-оксазин-1,4(3aH)-дион и способ синтеза его производных известны из уровня техники. Заявляемое соединение является продуктом взаимодействия 3-ароил-1H-бензо[b]пирроло[1,2-d][1,4]оксазин-1,2,4-трионов с 2-оксиндолом («Нуклеофильное присоединение оксиндола к пирролобензоксазинтрионам», Топанов П.А., Машевская И.В., Дмитриев М.В., Масливец А.Н., ЖОрХ, 2021, 57, №1, 127. [Nucleophilic Addition of Oxindole to Pyrrolobenzoxazinetriones. Topanov P.A., Mashevskaya I.V., Dmitriev M.V., Maslivets A.N. Russ. JOC, 2021, 57(1), 97-101. doi: 10.1134/S1070428021010152]), образуется по следующей схеме:Claimed compound 3-(4-chlorobenzoyl)-2-hydroxy-3a-(2-oxo-indolin-3-yl)-1H-benzo[b]pyrrolo[1,2-d][1,4]-oxazin- 1,4(3aH)-dione and a method for the synthesis of its derivatives are known from the prior art. The claimed compound is the product of the interaction of 3-aroyl-1H-benzo[b]pyrrolo[1,2-d][1,4]oxazine-1,2,4-triones with 2-oxindole (“Nucleophilic addition of oxindole to pyrrolobenzoxazinetriones”, Topanov P.A., Mashevskaya I.V., Dmitriev M.V., Maslivets A.N., ZHORH, 2021, 57, No. 1, 127. MV, Maslivets AN Russ. JOC, 2021, 57(1), 97-101. doi: 10.1134/S1070428021010152]), is formed as follows:
Противомикробная активность 3-ароил-2-гидрокси-3а-(2-оксо-индолин-3-ил)-1Н-бензо[b]пирроло[1,2-d][1,4]-оксазин-1,4(3aH)-дионов ранее не была исследована.Antimicrobial activity 3aH)-diones have not been previously studied.
Задачей изобретения является изыскание новых соединений, обладающих противомикробной активностью, и расширение арсенала средств воздействия на живой организм.The objective of the invention is to find new compounds with antimicrobial activity, and to expand the arsenal of means of influencing a living organism.
Поставленная задача решается тем, что соединение 3-(4-хлорбензоил)-2-гидрокси-3а-(2-оксо-индолин-3-ил)-1H-бензо[b]пирроло[1,2-d][1,4]-оксазин-1,4(3aH)-дион проявляет высокую противомикробную активность в концентрации в 1000 мкг/мл.The problem is solved by the fact that the compound 3-(4-chlorobenzoyl)-2-hydroxy-3а-(2-oxo-indolin-3-yl)-1H-benzo[b]pyrrolo[1,2-d][1, 4]-oxazine-1,4(3aH)-dione exhibits high antimicrobial activity at a concentration of 1000 μg/ml.
Синтезируют заявляемое соединение путем взаимодействия 3-(4-хлорбензоил)-1H-бензо[b]пирроло[1,2-d][1,4]оксазин-1,2,4-триона с 2-оксиндолом в среде растворителя с последующим выделением целевого продукта, по следующей схеме:The claimed compound is synthesized by reacting 3-(4-chlorobenzoyl)-1H-benzo[b]pyrrolo[1,2-d][1,4]oxazine-1,2,4-trione with 2-oxindole in a solvent medium, followed by isolation of the target product, according to the following scheme:
Процесс ведут при комнатной температуре, в качестве растворителя используют безводный ацетонитрил.The process is carried out at room temperature, anhydrous acetonitrile is used as a solvent.
Изобретение иллюстрируется следующими примерами.The invention is illustrated by the following examples.
Пример 1. 3-(4-хлорбензоил)-2-гидрокси-3а-(2-оксо-индолин-3-ил)-1Н-бензо[b]пирроло[1,2-d][1,4]-оксазин-1,4(3aH)-дион (3b).Example 1 3-(4-chlorobenzoyl)-2-hydroxy-3a-(2-oxo-indolin-3-yl)-1H-benzo[b]pyrrolo[1,2-d][1,4]-oxazine -1,4(3aH)-dione (3b).
К смеси 0.5 ммоль соединения 1b и 0.5 ммоль 2-оксиндола 2 в виале добавляли 3 мл абсолютного ацетонитрила, перемешивали при комнатной температуре в течение 24 ч, образовавшийся осадок отфильтровывали, промывали ацетонитрилом и горячим хлороформом. Выход 54%, т.пл. 197-199°С (CHCl3, разл.).To a mixture of 0.5 mmol of compound 1b and 0.5 mmol of 2-oxindole 2 in a vial was added 3 ml of absolute acetonitrile, stirred at room temperature for 24 h, the precipitate formed was filtered off, washed with acetonitrile and hot chloroform. Yield 54%, m.p. 197-199°C (CHCl 3 , decomp.).
Соединение (3b) C26H15ClN2O6.Compound (3b) C 26 H 15 ClN 2 O 6 .
Найдено, %: С 64.17; Н 3.09; N 5.77.Found, %: С 64.17; H 3.09; N 5.77.
Вычислено, %: С 64.14; Н 3.11; N 5.75.Calculated, %: С 64.14; H 3.11; N 5.75.
Соединение (3b) - бледно-желтое кристаллическое вещество с высокой температурой плавления, плавящееся с разложением, растворимое в ацетонитриле, 1,4-диоксане, этилацетате, легкорастворимое в ДМСО, ДМФА, ацетоне, нерастворимое в алканах и воде. Устойчиво при хранении в обычных условиях.Compound (3b) is a pale yellow crystalline substance with a high melting point, melting with decomposition, soluble in acetonitrile, 1,4-dioxane, ethyl acetate, freely soluble in DMSO, DMF, acetone, insoluble in alkanes and water. Stable when stored under normal conditions.
В ИК-спектре соединения (3b), записанном в виде пасты в вазелиновом масле, присутствуют полосы валентных колебаний гидроксильной и амидной групп (3387, 3258 см-1), 3 лактамных и 1 ароильной карбонильных групп (1778, 1733,1700, 1663 см-1).In the IR spectrum of compound (3b), recorded as a paste in vaseline oil, there are bands of stretching vibrations of the hydroxyl and amide groups (3387, 3258 cm -1 ), 3 lactam and 1 aroyl carbonyl groups (1778, 1733, 1700, 1663 cm -1 ).
В спектре ЯМР 1Н соединения (3b), записанном в растворе в ДМСО-d6, кроме сигналов протонов ароматических колец и связанных с ними групп, присутствуют синглеты протонов NH и С3Н индолинового фрагмента при 10.27 м.д. и 4.93 м.д.The 1 H NMR spectrum of the compound (3b), in a solution recorded in DMSO-d 6, except proton signals of aromatic rings and their associated groups are present singlets NH proton and C 3 H indoline moiety at 10.27 ppm and 4.93 ppm
соответственно. Из группы сигналов ароматических протонов в слабое поле смещается мультиплет орто-протонов ароильного заместителя (м, 2Н, 8.03-8.06 м.д.), а в сильное поле дублет протона С6Н (д, 1Н, 6.74 м.д., J 7.7 Гц).respectively. From the group of aromatic proton signals in the downfield shifts of protons ortho multiplet aroyl substituent (m, 2H, 8.03-8.06 ppm), and a strong proton doublet field C 6 H (d, 1H, 6.74 ppm, J 7.7 Hz).
Пример 2. Фармакологическое исследование соединения (3b) на наличие противомикробной активности.Example 2 Pharmacological study of compound (3b) for antimicrobial activity.
Для исследований использовали общепринятый метод двукратных серийных разведений в жидкой питательной среде микрометодом [Руководство по экспериментальному (доклиническому) изучению новых фармакологических веществ - М.: И-во Медицина, 2005]. Готовили исходные разведения микроорганизмов в физиологическом растворе из суточной агаровой культуры по оптическому стандарту мутности (ОСО) на 5 ME с использованием денситометра. После ряда разведений конечная концентрация клеток в опыте составляла 2,5×105 клеток/мл.For research, the generally accepted method of two-fold serial dilutions in a liquid nutrient medium by the micromethod was used [Guidelines for the experimental (preclinical) study of new pharmacological substances - M.: I-vo Medicine, 2005]. Initial dilutions of microorganisms in physiological saline were prepared from daily agar culture according to the optical turbidity standard (OCO) for 5 ME using a densitometer. After a series of dilutions, the final concentration of cells in the experiment was 2.5×10 5 cells/ml.
Противомикробные свойства химического вещества изучали на 3-х коллекционных условно-патогенных штаммах микроорганизмов: Staphylococcus aureus (штамм 906), Escherichia coli (штамм 1257), Candida albicans, 1353.The antimicrobial properties of the chemical were studied on 3 collection opportunistic strains of microorganisms: Staphylococcus aureus (strain 906), Escherichia coli (strain 1257), Candida albicans, 1353.
Соединение (3b) подавляет рост S. aureus в концентрации 250,0 мкг/мл, гибель культуры наступает от концентрации в 1000 мкг/мл.Compound (3b) inhibits the growth of S. aureus at a concentration of 250.0 μg/ml, the death of the culture occurs from a concentration of 1000 μg/ml.
Предлагаемое вещество 3-(4-хлорбензоил)-2-гидрокси-3а-(2-оксо-индолин-3-ил)-1H-бензо[b]пирроло[1,2-d][1,4]-оксазин-1,4(3aH)-дион (3b) обладает фармакологической активностью, а именно противомикробной активностью, и может найти применение в фармакологии в качестве потенциального лекарственного средства.Proposed substance 1,4(3aH)-dione (3b) has pharmacological activity, namely antimicrobial activity, and can be used in pharmacology as a potential drug.
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| RU2783264C1 (en) * | 2022-02-28 | 2022-11-10 | Федеральное государственное автономное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" | 3-(4-CHLOROBENZOYL)-2-HYDROXY-3a-(2-HYDROXY-4,4-DIMETHYL-6-OXOCYCLOHEX-1-en-1-yl)PYRROLO[1,2-a]QUINOXALIN-1,4 (3aH,5H)-DIONE WITH ANTIMICROBIAL ACTIVITY AND METHOD FOR ITS PRODUCTION |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1433789A1 (en) * | 2002-12-24 | 2004-06-30 | Aponetics AG | Pyrrolopyrazines and their use as selective apoptosis inducers |
| RU2665060C1 (en) * | 2018-03-07 | 2018-08-28 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" | Method for producing (r*)-3-aroyl-2-hydroxy-2-((s*)-2-oxocycloalkyl)pyrrolo[1,2-a]quinoxaline-1,4(2h,5h)-diones |
| RU2668969C1 (en) * | 2017-10-28 | 2018-10-05 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" | 10-benzyl-3,4-dibenzoyl-2'-oxo-1',2',10,10a-tetrahydrospiro[benzo[4,5]imidazo[2,1-b][1,3]oxazine-2,3'-pyrroles] |
| RU2743922C1 (en) * | 2020-06-25 | 2021-03-01 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" | 2'-amino-2,5'-dioxo-5-phenyl-1,2,5',6',7',8'-hexahydro-1'h-spiro[pyrrol-3,4'-quinolines] |
-
2021
- 2021-06-23 RU RU2021119135A patent/RU2763730C1/en active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1433789A1 (en) * | 2002-12-24 | 2004-06-30 | Aponetics AG | Pyrrolopyrazines and their use as selective apoptosis inducers |
| RU2668969C1 (en) * | 2017-10-28 | 2018-10-05 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" | 10-benzyl-3,4-dibenzoyl-2'-oxo-1',2',10,10a-tetrahydrospiro[benzo[4,5]imidazo[2,1-b][1,3]oxazine-2,3'-pyrroles] |
| RU2665060C1 (en) * | 2018-03-07 | 2018-08-28 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" | Method for producing (r*)-3-aroyl-2-hydroxy-2-((s*)-2-oxocycloalkyl)pyrrolo[1,2-a]quinoxaline-1,4(2h,5h)-diones |
| RU2743922C1 (en) * | 2020-06-25 | 2021-03-01 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" | 2'-amino-2,5'-dioxo-5-phenyl-1,2,5',6',7',8'-hexahydro-1'h-spiro[pyrrol-3,4'-quinolines] |
Non-Patent Citations (1)
| Title |
|---|
| TOPANOV ET AL., Russian Journal of Organic Chemistry, Vol. 56, No. 4, 2020, pp. 719-722. * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2783264C1 (en) * | 2022-02-28 | 2022-11-10 | Федеральное государственное автономное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" | 3-(4-CHLOROBENZOYL)-2-HYDROXY-3a-(2-HYDROXY-4,4-DIMETHYL-6-OXOCYCLOHEX-1-en-1-yl)PYRROLO[1,2-a]QUINOXALIN-1,4 (3aH,5H)-DIONE WITH ANTIMICROBIAL ACTIVITY AND METHOD FOR ITS PRODUCTION |
| RU2786502C1 (en) * | 2022-02-28 | 2022-12-21 | Федеральное государственное автономное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" | Application of 3-aroyl-2-hydroxy-3a-(2-oxoindolin-3-yl)-1h-benzo[b]pyrrolo[1,2-d][1,4]-oxazine-1,4(3ah)- diones, 3-aroyl-2-hydroxy-3a-(2-oxo-5-fluorindolin-3-yl)-1h-benzo[b]pyrrolo[1,2-d][1,4]-oxazin-1, 4(3ah)-diones as agents with anti-inflammatory activity |
| RU2810316C1 (en) * | 2023-03-28 | 2023-12-26 | Федеральное государственное автономное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" | 2A-METHOXYCARBONYL-8-CHLORO-1H,4H-SPIRO[BENZO[b]CYCLOPROPA[2,3]PYRROLO[1,2-d][1,4]OXAZINE-3,3'-INDOLINE]-1,2,2',4(2aH)-TETRAONE |
| RU2831251C1 (en) * | 2024-04-15 | 2024-12-03 | Федеральное государственное автономное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" | METHOD OF PRODUCING 3-HYDROXY-1-(2-HYDROXYPHENYL)-7a-(1H-INDOL-3-YL)-4-PHENYL-1,7a-DIHYDRO-2H-PYRROLO[2,3-d]PYRIDAZINE-2,7(6h)-DIONE AS AGENT HAVING ANTI-TUBERCULOSIS ACTIVITY |
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