RU2017145952A - Несимметричные производные полифенолов динафталинового ряда, способ их получения и применение - Google Patents

Несимметричные производные полифенолов динафталинового ряда, способ их получения и применение Download PDF

Info

Publication number
RU2017145952A
RU2017145952A RU2017145952A RU2017145952A RU2017145952A RU 2017145952 A RU2017145952 A RU 2017145952A RU 2017145952 A RU2017145952 A RU 2017145952A RU 2017145952 A RU2017145952 A RU 2017145952A RU 2017145952 A RU2017145952 A RU 2017145952A
Authority
RU
Russia
Prior art keywords
amount
substituents
gossypol
organic
sodium
Prior art date
Application number
RU2017145952A
Other languages
English (en)
Other versions
RU2766222C2 (ru
RU2017145952A3 (ru
Inventor
Владимир Георгиевич Нестеренко
Анатолий Петрович Суслов
Сергей Александрович Цырульников
Михаил Николаевич НЕНАШЕВ
Ирина Владиславовна КИСЕЛЕВА
Виталий Владимирович Кузнецов
Original Assignee
Общество С Ограниченной Ответственностью "Ниармедик Плюс"
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Общество С Ограниченной Ответственностью "Ниармедик Плюс" filed Critical Общество С Ограниченной Ответственностью "Ниармедик Плюс"
Priority to RU2017145952A priority Critical patent/RU2766222C2/ru
Priority to US16/958,618 priority patent/US20200369618A1/en
Priority to EP18845453.2A priority patent/EP3731933A1/en
Priority to EA202091548A priority patent/EA202091548A1/ru
Priority to MA051424A priority patent/MA51424A/fr
Priority to PCT/RU2018/050169 priority patent/WO2019132739A1/en
Priority to JP2020536759A priority patent/JP2021509115A/ja
Publication of RU2017145952A publication Critical patent/RU2017145952A/ru
Publication of RU2017145952A3 publication Critical patent/RU2017145952A3/ru
Application granted granted Critical
Publication of RU2766222C2 publication Critical patent/RU2766222C2/ru

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
    • 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
    • A61K31/11—Aldehydes
    • 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
    • A61K31/12—Ketones
    • A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
    • 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
    • A61P31/12—Antivirals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/10—Hydrazines
    • C07C243/12—Hydrazines having nitrogen atoms of hydrazine groups bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/10—Hydrazines
    • C07C243/12—Hydrazines having nitrogen atoms of hydrazine groups bound to acyclic carbon atoms
    • C07C243/16—Hydrazines having nitrogen atoms of hydrazine groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
    • C07C243/18—Hydrazines having nitrogen atoms of hydrazine groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
    • C07C245/12—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
    • C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/13—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/202—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a naphthalene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C46/00—Preparation of quinones
    • C07C46/02—Preparation of quinones by oxidation giving rise to quinoid structures
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/56—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups
    • C07C47/57—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C50/00—Quinones
    • C07C50/38—Quinones containing —CHO or non—quinoid keto groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
    • C07C69/33—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with hydroxy compounds having more than three hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers
    • C07C69/736—Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/75—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of acids with a six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/78—Benzoic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/95—Esters of quinone carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
    • C07D211/56—Nitrogen atoms
    • C07D211/58—Nitrogen atoms attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/68—One oxygen atom attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oncology (AREA)
  • Virology (AREA)
  • Communicable Diseases (AREA)
  • Emergency Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Claims (51)

1. Соединение общей формулы I:
Figure 00000001
I
или общей формулы II
Figure 00000002
II
их таутомерные формы, фармацевтически приемлемые соли и сольваты,
где:
R1 представляет собой: C(O)H, C=N-R8, С=N-NН-R8, С=N-NН-С(О)R8;
где R8 представляет собой: H; линейные и разветвленные С1-С20 алкилы, содержащие заместители в количестве от 0 до 10; линейные и разветвленные С2-С20 алкенилы и С2-С20 алкинилы с количеством двойных и (или) тройных связей от 1 до 9, содержащие заместители в количестве от 0 до 10; незамещенные и замещенные циклические системы с числом атомов в цикле от 3 до 20, содержащие заместители в количестве от 0 до 10, количеством двойных и (или) тройных связей от 0 до 10 и количеством гетероатомов (N, S, O) от 0 до 10; незамещенные и замещенные арилы с заместителями в количестве от 0 до 5, незамещенные и замещенные гетероароматические соединения с числом атомов в цикле от 3 до 12 и количеством гетероатомов (N, S, O) от 1 до 6, содержащие заместители в количестве от 0 до 10; насыщенные, ненасыщенные и (или) ароматические полициклические системы, содержащие от 2 до 5 циклов с числом атомов в цикле от 3 до 8, количеством двойных и (или) тройных связей от 0 до 10 и количеством гетероатомов (N, S, O) от 0 до 10 и заместители в количестве от 0 до 20;
R2, R3, R2a, R3a, R7, R7a независимо представляют собой R8 или C(O)R8;
R5 и R5a независимо представляют собой H или N=N-R9;
где R9 представляет собой: незамещенные и замещенные арилы с заместителями в количестве от 0 до 5, незамещенные и замещенные гетероароматические соединения с числом атомов в цикле от 3 до 12 и количеством гетероатомов (N, S, O) от 1 до 6, содержащие заместители в количестве от 0 до 10; насыщенные, ненасыщенные и (или) ароматические полициклические системы, содержащие от 2 до 5 циклов с числом атомов в цикле от 3 до 8 и количеством гетероатомов (N, S, O) от 0 до 10 и заместители в количестве от 0 до 20;
R4, R4a, R6 и R6a независимо представляют собой H, линейные и разветвленные С1-С10 алкилы;
где заместители представляют собой Н, F, Cl, Br, I, NO2, CN, SO3H, SO3M, SO2Cl, CF3, CCl3, CBr3, CI3, C(O)H, COOH, COOМ, C(O)Cl, C(O)Br, C(O)I, R8, COOR8, C(O)R8, OH, OR8, ОС(О)R8, OC(O)NR8R10, ОSO2R8, NH2, NR8R10, N+(R8R10R11), NR8C(O)R10, NR8SO2R10, NR8C(O)NR10R11, SR8, S(O)R8, SO2R8, CH=NR8;
где R10, R11 независимо представляют собой: H; линейные и разветвленные С1-С20 алкилы, содержащие заместители в количестве от 0 до 10; линейные и разветвленные С2-С20 алкенилы и С2-С20 алкинилы с количеством двойных и (или) тройных связей от 1 до 9, содержащие заместители в количестве от 0 до 10; незамещенные и замещенные циклические системы с числом атомов в цикле от 3 до 20, содержащие заместители в количестве от 0 до 10, количеством двойных и (или) тройных связей от 0 до 10 и количеством гетероатомов (N, S, O) от 0 до 10; незамещенные и замещенные арилы с заместителями в количестве от 0 до 5, незамещенные и замещенные гетероароматические соединения с числом атомов в цикле от 3 до 12 и количеством гетероатомов (N, S, O) от 1 до 6, содержащие заместители в количестве от 0 до 10; насыщенные, ненасыщенные и (или) ароматические полициклические системы, содержащие от 2 до 5 циклов с числом атомов в цикле от 3 до 8, количеством двойных и (или) тройных связей от 0 до 10 и количеством гетероатомов (N, S, O) от 0 до 10 и заместители в количестве от 0 до 20;
где М представляет собой Li, Na, K, Cs, Rb.
2. Соединение, имеющее структуру, представленную в Таблице 1:
Таблица 1 I
Figure 00000003
 II
Figure 00000004
 III
Figure 00000005
 IV
Figure 00000006
 V
Figure 00000007
 VI
Figure 00000008
 VII
Figure 00000009
 VIII
Figure 00000010
 IX
Figure 00000011
 X
Figure 00000012
 XI
Figure 00000013
 XII
Figure 00000014
 XIII
Figure 00000015
 XIV
Figure 00000016
 XV
Figure 00000017
 XVI
Figure 00000018
 XVII
Figure 00000019
 XVIII
Figure 00000020
 XIX
Figure 00000021
 XX
Figure 00000022
 XXI
Figure 00000023
 XXII
Figure 00000024
 XXIII
Figure 00000025
 XXIV
Figure 00000026
 XXV
Figure 00000027
 XXVI
Figure 00000028
 XXVII
Figure 00000029
 XXVIII
Figure 00000030
 XXIX
Figure 00000031
 XXX
Figure 00000032
 XXXI
Figure 00000033
 XXXII
Figure 00000034
 XXXIII
Figure 00000035
 XXXIV
Figure 00000036
 XXXV
Figure 00000037
 XXXVI
Figure 00000038
 XXXVII
Figure 00000039
 XXXVIII
Figure 00000040
 XXXIX
Figure 00000041
 XL
Figure 00000042
 XL1
Figure 00000043
 XLII
Figure 00000044
 XLIII
Figure 00000045
 XLIV
Figure 00000046
 XLV
Figure 00000047
 XLVI
Figure 00000048
 XLVII
Figure 00000049
 XLVIII
Figure 00000050
 XLIX
Figure 00000051
 L
Figure 00000052
 LI
Figure 00000053
 LII
Figure 00000054
 LIII
Figure 00000055
 LIV
Figure 00000056
 LV
Figure 00000057
 LVI
Figure 00000058
 LVII
Figure 00000059
 LVIII
Figure 00000060
 LIX
Figure 00000061
 LX
Figure 00000062
 LXI
Figure 00000063
 LXII
Figure 00000064
3. Способ получения соединения общей формулы (I) по п.1, включающий стадии:
-обработки производного госсипола, необязательно в форме его сольвата, водным раствором гидроксида щелочного и/или щелочноземельного металла;
- обработки полученной реакционной смеси органическими и/или неорганическими кислотами до рН=0,1-10, предпочтительно 3-5;
-выделения и очистки полученного продукта;
- и, в случае необходимости, последующую обработку полученного продукта реакционным агентом, который выбирают из группы, содержащей: алифатические, ароматические или гетероароматические амины; алкилирующие агенты; ацилирующие агенты; соли диазония; и
- выделение и очистку целевого продукта.
4. Способ по п.3, где производное госсипола представляет собой госсипол, госсиполуксусную кислоту, метиловые эфиры госсипола.
5. Способ по п.3 или 4, где производное госсипола обрабатывают водным раствором гидроксида калия или натрия.
6. Способ по любому из пп.3-5, где концентрация водного раствора гидроксида щелочного и/или щелочноземельного металла составляет 0,1-50 мас. %, предпочтительно 10-30 мас.%.
7. Способ по любому из пп.3-6, где обработку алифатическими, ароматическими или гетероароматическими аминами проводят в растворителе, таком как изопропанол, диэтиловый эфир, диоксан или тетрагидрофуран.
8. Способ по любому из пп.3-6, где в качестве алкилирующих агентов используют ароматические или алифатические галогенпроизводные или алкилсульфаты и обработку проводят в присутствии органических и/или неорганических оснований, таких как карбонат цезия, этилат натрия, трет-бутилат калия, триэтиламин или гидрид натрия, в растворителе, таком как изопропанол, диэтиловый эфир или тетрагидрофуран.
9. Способ по любому из пп.3-6, где в качестве ацилирующего агента используют карбоновые кислоты или галогенангидриды, или обработку проводят в присутствии органических и неорганических оснований, таких как карбонат калия, карбонат цезия, метилат натрия, этилат натрия, трет-бутилат калия, триэтиламин, диизопропиламин или гидрид натрия, необязательно в присутствии реагентов сочетания, таких как карбонилдиимидазол, ДЦК в растворителе, таком как хлороформ, тетрагидрофуран или диоксан.
10. Способ по любому из пп.3-6, где обработку солями диазония проводят в водной среде и/или растворителе, таком как этанол или диэтиловый эфир.
11. Способ получения соединения общей формулы (II) по п.1, включающий стадии:
-обработки производного госсипола, необязательно в форме его сольвата, водным раствором гидроксида щелочного и/или щелочноземельного металла;
- обработки полученной реакционной смеси органическими и/или неорганическими кислотами до рН=0,1-10, предпочтительно 3-5;
- выделения и очистки полученного продукта;
- последующей обработки полученного продукта перекисью водорода в концентрации 0,1-99,8% в органических и/или неорганических кислотах; или
- последующей обработки полученного продукта соединениями трехвалентного железа в присутствии органического растворителя и/или органической или неорганической кислоты;
- выделения и очистки полученного продукта; и
- в случае необходимости, последующую обработку полученного продукта реакционным агентом, который выбирают из группы, содержащей: алифатические, ароматические или гетероароматические амины; алкилирующие агенты и ацилирующие агенты; и
- выделение и очистку целевого продукта.
12. Способ по п.11, где производное госсипола представляет собой госсипол, госсиполуксусную кислоту, метиловые эфиры госсипола.
13. Способ по п.11 или 12, где производное госсипола обрабатывают водным раствором гидроксидам калия или натрия.
14. Способ по любому из пп.11-13, где концентрация водного раствора гидроксида щелочного и/или щелочноземельного металла составляет 0,1-50 мас. %, предпочтительно 10-30 мас.%.
15. Способ по любому из пп.11-13, где перекись водорода используют в концентрации 1-30 мас.% и обработку проводят в среде уксусной кислоты.
16. Способ по любому из пп.11-13, где соединение трехвалентного железа представляет собой хлорид железа (III) в твердом виде или в водном растворе и обработку проводят в среде ацетона и/или уксусной кислоты.
17. Способ по любому из пп.11-16, где обработку алифатическими, ароматическими или гетероароматическими аминами проводят в растворителе, таком как изопропанол, диэтиловый эфир, диоксан или тетрагидрофуран.
18. Способ по любому из пп.11-16, где в качестве алкилирующих агентов используют ароматические или алифатические галогенпроизводные или алкилсульфаты и обработку проводят в присутствии органических и неорганических оснований, таких как карбонат цезия, этилат натрия, трет-бутилат калия, триэтиламин или гидрид натрия, в растворителе, таком как изопропанол, диэтиловый эфир или тетрагидрофуран.
19. Способ по любому из пп.11-16, где в качестве ацилирующего агента используют карбоновые кислоты и/или галогенангидриды, или обработку проводят в присутствии органических и неорганических оснований, таких как карбонат калия, карбонат цезия, метилат натрия, этилат натрия, трет-бутилат калия, триэтиламин, диизопропиламин или гидрид натрия, необязательно в присутствии реагентов сочетания, таких как карбонилдиимидазол, ДЦК в растворителе, таком как хлороформ, тетрагидрофуран или диоксан.
20. Противовирусное средство, представляющее собой соединение общей формулы (I) или (II) по п.1 или соединение по п.2.
21. Противовирусное средство по п.20, эффективное в отношении вирусов гриппа, герпеса, гепатита, ВИЧ.
RU2017145952A 2017-12-26 2017-12-26 Несимметричные производные полифенолов динафталинового ряда, способ их получения и применение RU2766222C2 (ru)

Priority Applications (7)

Application Number Priority Date Filing Date Title
RU2017145952A RU2766222C2 (ru) 2017-12-26 2017-12-26 Несимметричные производные полифенолов динафталинового ряда, способ их получения и применение
US16/958,618 US20200369618A1 (en) 2017-12-26 2018-12-25 Asymmetric derivatives of polyphenols of the dinaphthaline series, process of preparing and use thereof
EP18845453.2A EP3731933A1 (en) 2017-12-26 2018-12-25 Asymmetric derivatives of polyphenols of the dinaphthaline series, process of preparing and use thereof
EA202091548A EA202091548A1 (ru) 2017-12-26 2018-12-25 Несимметричные производные полифенолов динафталинового ряда, способ их получения и применение
MA051424A MA51424A (fr) 2017-12-26 2018-12-25 Dérivés asymétriques de polyphénols de la série dinaphtaline, leur procédé de préparation et leur utilisation
PCT/RU2018/050169 WO2019132739A1 (en) 2017-12-26 2018-12-25 Asymmetric derivatives of polyphenols of the dinaphthaline series, process of preparing and use thereof
JP2020536759A JP2021509115A (ja) 2017-12-26 2018-12-25 ジナフタリン系列のポリフェノールの非対称誘導体、その調製方法、及びその使用

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
RU2017145952A RU2766222C2 (ru) 2017-12-26 2017-12-26 Несимметричные производные полифенолов динафталинового ряда, способ их получения и применение

Publications (3)

Publication Number Publication Date
RU2017145952A true RU2017145952A (ru) 2019-06-27
RU2017145952A3 RU2017145952A3 (ru) 2019-07-17
RU2766222C2 RU2766222C2 (ru) 2022-02-10

Family

ID=65363349

Family Applications (1)

Application Number Title Priority Date Filing Date
RU2017145952A RU2766222C2 (ru) 2017-12-26 2017-12-26 Несимметричные производные полифенолов динафталинового ряда, способ их получения и применение

Country Status (7)

Country Link
US (1) US20200369618A1 (ru)
EP (1) EP3731933A1 (ru)
JP (1) JP2021509115A (ru)
EA (1) EA202091548A1 (ru)
MA (1) MA51424A (ru)
RU (1) RU2766222C2 (ru)
WO (1) WO2019132739A1 (ru)

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MA21995A1 (fr) * 1989-11-13 1991-07-01 Menarini Farma Ind Nouvelles fluoronaphthacenediones,leurs derives glycozyles et leurs procedes de fabrication .
CN101327201B (zh) * 2007-06-20 2013-02-13 上海市计划生育科学研究所 棉酚或其类似物的液体制剂及其制备方法和用途
FR2924712B1 (fr) * 2007-12-06 2012-12-21 Univ Maine Derives du gossypol et de l'apogossypol, leurs preparations et leurs applications
CN104910041B (zh) * 2014-03-12 2017-09-26 南开大学 棉酚的芳香胺席夫碱衍生物及其制备方法和抗植物病毒应用
CN105884634B (zh) * 2015-01-05 2019-06-04 南开大学 棉酚衍生物和它们的制备,在农药上的应用及抗癌活性

Also Published As

Publication number Publication date
EP3731933A1 (en) 2020-11-04
RU2766222C2 (ru) 2022-02-10
RU2017145952A3 (ru) 2019-07-17
WO2019132739A1 (en) 2019-07-04
JP2021509115A (ja) 2021-03-18
US20200369618A1 (en) 2020-11-26
MA51424A (fr) 2020-11-04
EA202091548A1 (ru) 2020-09-17

Similar Documents

Publication Publication Date Title
Kubo et al. Nonpeptide angiotensin II receptor antagonists. Synthesis and biological activity of potential prodrugs of benzimidazole-7-carboxylic acids
FI88163C (fi) Foerfarande foer framstaellning av farmaceutiskt anvaendbara pyrazolo/3,4-d/pyrimidiner
PE20001484A1 (es) Derivados de naftalen-1-ilo urea y acido carbamico
YU47124B (sh) Postupak za dobijanje novih derivata 7-(1-azetidinil)-1,4-dihidro-4-oksokinolein-3-karboks ilnih kiselina
RU2017145952A (ru) Несимметричные производные полифенолов динафталинового ряда, способ их получения и применение
Rezayati et al. Phospho sulfonic acid catalyzed synthesis of benzimidazole, benzoxazole and quinoxaline derivatives under green solvent at ambient temperature
NZ245674A (en) Imidazole derivatives and anti-hiv medicaments
RU2015102043A (ru) Новые пролекарства ребамипида, способ их получения и применение
FI59802B (fi) Foerfarande foer framstaellning av farmakologiskt vaerdefulla nya substituerade 2-fenylamino-imidazoliner-(2) och deras syraadditionssalter
KR930001414B1 (ko) 아졸 유도체와 그의 약제학적으로 허용가능한 염
Soria-Arteche et al. Studies on the selective S-oxidation of albendazole, fenbendazole, triclabendazole, and other benzimidazole sulfides
SU419022A3 (ru)
AR125990A1 (es) Intermediario novedoso para la preparación de piroxasulfona
DK154295B (da) Analogifremgangsmaade til fremstilling af 2-nitroimidazol-derivater
FR3099478B1 (fr) Procédé de traitement d’une composition comprenant de la vanilline naturelle
SU557756A3 (ru) Способ получени изохинолинов или их солей
GB853129A (en) New pyrrolo derivatives and process for their manufacture
US3920655A (en) Nitroimidazolyl benzoquinazolines
CS269077B1 (cs) Způsob přípravy 5-azacytosinů
Dubey et al. Synthesis of 1-(n-hexyl-5-one)-2-chlorobenzimidazole
CA2306428C (fr) Derives de la 3-oxo-2(h)-1,2,4 - triazine en tant que ligands des recepteurs 5ht1a
WO2016070241A1 (en) Triazine compounds, compositions and synthesis
SU655307A3 (ru) Способ получени производных гуанидинов или их солей
CS240963B2 (en) Production method of indolizine derivatives
JP2524420B2 (ja) ピペリジン誘導体及びそれらを有効成分とする抗潰瘍剤

Legal Events

Date Code Title Description
HZ9A Changing address for correspondence with an applicant
HZ9A Changing address for correspondence with an applicant