RU2017123588A - Derivatives of coumarin, thiocoumarin and quinolinone with anticonvulsant activity - Google Patents

Derivatives of coumarin, thiocoumarin and quinolinone with anticonvulsant activity Download PDF

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RU2017123588A
RU2017123588A RU2017123588A RU2017123588A RU2017123588A RU 2017123588 A RU2017123588 A RU 2017123588A RU 2017123588 A RU2017123588 A RU 2017123588A RU 2017123588 A RU2017123588 A RU 2017123588A RU 2017123588 A RU2017123588 A RU 2017123588A
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derivatives
aminocarboxylic acids
general formula
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aminobutyric acid
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RU2720510C2 (en
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Григорий Владимирович Мокров
Светлана Александровна Литвинова
Любовь Николаевна Неробкова
Иван Георгиевич Ковалев
Татьяна Александровна Гудашева
Татьяна Александровна Воронина
Андрей Дмитриевич Дурнев
Сергей Борисович Середенин
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Федеральное государственное бюджетное научное учреждение "Научно-исследовательский институт фармакологии имени В.В. Закусова"
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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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365—Lactones
    • A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
    • A61K31/37—Coumarins, e.g. psoralen
    • 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
    • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
    • A61K31/382—Heterocyclic compounds having sulfur as a ring hetero atom having six-membered rings, e.g. thioxanthenes
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4704—2-Quinolinones, e.g. carbostyril
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C07D215/42—Nitrogen atoms attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
    • C07D311/12—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 3 and unsubstituted in position 7
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
    • C07D311/14—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 6 and unsubstituted in position 7
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
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  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Psychiatry (AREA)
  • Hospice & Palliative Care (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Claims (26)

1. Замещенные (кумарин-4-ил)аминокарбоновые кислоты, (тиокумарин-4-ил)аминокарбоновые кислоты, (2-оксо-1,2-дигидрохинолин-4-ил)аминокарбоновые кислоты и их производные общей формулы (1.1-1.3):1. Substituted (coumarin-4-yl) aminocarboxylic acids, (thiocoumarin-4-yl) aminocarboxylic acids, (2-oxo-1,2-dihydroquinolin-4-yl) aminocarboxylic acids and their derivatives of the general formula (1.1-1.3) :
Figure 00000001
,
Figure 00000001
, где R может быть атомом водорода или нитро-группой; n может принимать значения от 3 до 6; X может быть О (1.1), S (1.2), NH (1.3); Y может быть ОН, ОСН3, ОС2Н5, NH2, NHCH3 группами.where R may be a hydrogen atom or a nitro group; n may range from 3 to 6; X may be O (1.1), S (1.2), NH (1.3); Y may be OH, OCH 3 , OS 2 H 5 , NH 2 , NHCH 3 groups. 2. Соединение по п. 1, представляющее собой N-(3-нитрокумарин-4-ил)-4-аминомасляную кислоту (1.1а).2. The compound according to claim 1, which is N- (3-nitrocoumarin-4-yl) -4-aminobutyric acid (1.1a). 3. Соединение по п. 1, представляющее собой N-(3,6-динитрокумарин-4-ил)-4-аминомасляную кислоту (1.1 в).3. The compound according to claim 1, which is N- (3,6-dinitrocoumarin-4-yl) -4-aminobutyric acid (1.1 c). 4. Соединение по п. 1, представляющее собой метиловый эфир N-(3-нитрокумарин-4-ил)-4-аминомасляной кислоты (1.1 г).4. The compound according to claim 1, which is a methyl ester of N- (3-nitrocoumarin-4-yl) -4-aminobutyric acid (1.1 g). 5. Соединение по п. 1, представляющее собой метиловый эфир N-(3,6-динитрокумарин-4-ил)-4-аминомасляной кислоты (1.1 д).5. The compound according to claim 1, which is a methyl ester of N- (3,6-dinitrocoumarin-4-yl) -4-aminobutyric acid (1.1 d). 6. Соединение по п. 1, представляющее собой N-(3-нитро-1-тиокумарин-4-ил)-4-аминомасляную кислоту (1.2а).6. The compound according to claim 1, which is N- (3-nitro-1-thiocoumarin-4-yl) -4-aminobutyric acid (1.2a). 7. Соединение по п. 1, представляющее собой метиловый эфир N-(3-нитротиокумарин-4-ил)-4-аминомасляной кислоты (1.2б).7. The compound according to claim 1, which is a methyl ester of N- (3-nitrothiocoumarin-4-yl) -4-aminobutyric acid (1.2b). 8. Соединение по п. 1, представляющее собой метиловый эфир N-(3-нитро-2-оксо-1,2-дигидрохинолин-4-ил)-4-аминомасляной кислоты (1.3а).8. The compound according to claim 1, which is a methyl ester of N- (3-nitro-2-oxo-1,2-dihydroquinolin-4-yl) -4-aminobutyric acid (1.3a). 9. Соединение по п. 1, представляющее собой N-(3-нитро-2-оксо-1,2-дигидрохинолин-4-ил)-4-аминомасляную кислоту (1.3б).9. The compound according to claim 1, which is N- (3-nitro-2-oxo-1,2-dihydroquinolin-4-yl) -4-aminobutyric acid (1.3b). 10. Способ получения (кумарин-4-ил)аминокарбоновых кислот и их производных общей формулы (1.1), где R, n и Y имеют вышеуказанные значения по п. 1, заключающийся в том, что 3-нитро-4-хлоркумарины общей формулы (2):10. The method of obtaining (coumarin-4-yl) aminocarboxylic acids and their derivatives of the General formula (1.1), where R, n and Y have the above values according to claim 1, namely that 3-nitro-4-chlorocoumarins of the general formula (2):
Figure 00000002
,
Figure 00000002
, где R имеют вышеуказанные значения, вводят во взаимодействие с аминокарбоновыми кислотами или их производными общей формулы (3):where R have the above meanings, enter into interaction with aminocarboxylic acids or their derivatives of General formula (3):
Figure 00000003
,
Figure 00000003
, где n и Y имеют вышеуказанные значения, в различных растворителях, таких как: бензол, толуол, этилацетат, диоксан, этанол, или подобных, при этом реакции могут проводиться как при избытке соединений (3), так и в присутствии оснований, таких как органические третичные амины, например, триэтиламин, или пиридин.where n and Y have the above meanings, in various solvents, such as: benzene, toluene, ethyl acetate, dioxane, ethanol, or the like, while the reaction can be carried out both with an excess of compounds (3), and in the presence of bases, such as organic tertiary amines, for example triethylamine, or pyridine. 11. Способ получения (тиокумарин-4-ил)аминокарбоновых кислот и их производных общей формулы (1.2), где R является атомом водорода, n и Y имеют вышеуказанные значения по п. 1, заключающийся в том, что 3-нитро-4-хлортиокумарин (4):11. The method of obtaining (thiocoumarin-4-yl) aminocarboxylic acids and their derivatives of the general formula (1.2), where R is a hydrogen atom, n and Y have the above values according to claim 1, namely, that 3-nitro-4- chlorothiocoumarin (4):
Figure 00000004
Figure 00000004
 вводят во взаимодействие с аминокарбоновыми кислотами или их производными общей формулы (3):
Figure 00000005
,enter into interaction with aminocarboxylic acids or their derivatives of General formula (3):
Figure 00000005
, где n Y имеют вышеуказанные значения, в различных растворителях, таких как: бензол, толуол, этилацетат, диоксан, этанол, или подобных, при этом реакции могут проводиться как при избытке соединений (3), так и в присутствии оснований, таких как органические третичные амины, например, триэтиламин, или пиридин.where n Y have the above meanings, in various solvents, such as: benzene, toluene, ethyl acetate, dioxane, ethanol, or the like, while the reaction can be carried out both with an excess of compounds (3), and in the presence of bases, such as organic tertiary amines, for example triethylamine, or pyridine. 12. Способ получения (2-оксо-1,2-дигидрохинолин-4-ил)аминокарбоновых кислот и их производных общей формулы (1.3), где R является атомом водорода, n и Y имеют вышеуказанные значения по п. 1, заключающийся в том, что 3-нитро-4-хлорхинолин-2(1H)-он (10):12. The method of obtaining (2-oxo-1,2-dihydroquinolin-4-yl) aminocarboxylic acids and their derivatives of the general formula (1.3), where R is a hydrogen atom, n and Y have the above values according to claim 1, which consists in that 3-nitro-4-chloroquinolin-2 (1H) -one (10):
Figure 00000006
Figure 00000006
 вводят во взаимодействие с аминокарбоновыми кислотами или их производными общей формулы (3):enter into interaction with aminocarboxylic acids or their derivatives of General formula (3):
Figure 00000007
,
Figure 00000007
, где n и Y имеют вышеуказанные значения, в различных растворителях, таких как: бензол, толуол, этилацетат, диоксан, этанол, или подобных, при этом реакции могут проводиться как при избытке соединений (3), так и в присутствии оснований, таких как органические третичные амины, например, триэтиламин, или пиридин, также взаимодействие соединений 3 и 10 может производиться с использованием в качестве растворителя пиридина.where n and Y have the above meanings, in various solvents, such as: benzene, toluene, ethyl acetate, dioxane, ethanol, or the like, while the reaction can be carried out both with an excess of compounds (3), and in the presence of bases, such as organic tertiary amines, for example triethylamine, or pyridine, also the interaction of compounds 3 and 10 can be carried out using pyridine as a solvent. 13. Метод лечения эпилепсии и пароксизмальных состояний путем введения эффективных количеств соединений по пп. 1-9.13. A method of treating epilepsy and paroxysmal conditions by administering effective amounts of the compounds of claims. 1-9.
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