EA201300122A1 - Циклические n,n'-диарилтиомочевины и n,n'-диарилмочевины - антагонисты андрогеновых рецепторов, противораковое средство, способ получения и применения - Google Patents

Циклические n,n'-диарилтиомочевины и n,n'-диарилмочевины - антагонисты андрогеновых рецепторов, противораковое средство, способ получения и применения

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Publication number
EA201300122A1
EA201300122A1 EA201300122A EA201300122A EA201300122A1 EA 201300122 A1 EA201300122 A1 EA 201300122A1 EA 201300122 A EA201300122 A EA 201300122A EA 201300122 A EA201300122 A EA 201300122A EA 201300122 A1 EA201300122 A1 EA 201300122A1
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Eurasian Patent Office
Prior art keywords
methyl
hydrogen
cyclic
group
carbon atom
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EA201300122A
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English (en)
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EA020681B1 (ru
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Александр Васильевич ИВАЩЕНКО
Олег Дмитриевич МИТЬКИН
Original Assignee
Александр Васильевич ИВАЩЕНКО
ИВАЩЕНКО, Андрей Александрович
САВЧУК, Николай Филиппович
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Application filed by Александр Васильевич ИВАЩЕНКО, ИВАЩЕНКО, Андрей Александрович, САВЧУК, Николай Филиппович filed Critical Александр Васильевич ИВАЩЕНКО
Publication of EA201300122A1 publication Critical patent/EA201300122A1/ru
Publication of EA020681B1 publication Critical patent/EA020681B1/ru

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
    • C07D233/86—Oxygen and sulfur atoms, e.g. thiohydantoin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2013—Organic compounds, e.g. phospholipids, fats
    • A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2095—Tabletting processes; Dosage units made by direct compression of powders or specially processed granules, by eliminating solvents, by melt-extrusion, by injection molding, by 3D printing
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4841—Filling excipients; Inactive ingredients
    • A61K9/4858—Organic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/08—Drugs for disorders of the urinary system of the prostate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/74—Two oxygen atoms, e.g. hydantoin with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
    • C07D239/10—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring

Abstract

Настоящее изобретение относится к новым циклическим N,N'-диарилмочевинам и N,N'-диарилтиомочевинам - антагонистам андрогеновых рецепторов, противораковому средству, фармацевтической композиции, лекарственному средству и способу лечения раковых заболеваний, в том числе рака простаты. Предложены циклические N,N'-диарилтиомочевины или N,N'-диарилмочевины общей формулы 1, их оптические (R)- и (S)-изомеры и их фармацевтически приемлемые соли, обладающие свойствами антагонистов андрогеновых рецепторовгде X представляет собой кислород или серу; m=0 или 1; R1 представляет собой С-Салкил; R2 и R3 представляют собой водород; или R2 и R3 вместе с атомом углерода, с которым они связаны, образуют группу С=О; R4 и R5 представляют собой водород; или R4 представляет собой водород, a R5 представляет собой метил; или R4 представляет собой метил, R5 представляет собой CHR6-группу, в которой R6 представляет собой С-Салкоксикарбонил, карбоксил, необязательно замещенную гидроксильную группу, в которой заместителями могут быть водород, метил, бензил; или R4 и R5 вместе с атомом углерода, с которым они связаны, образуют пяти- или шестичленный насыщенный гетероцикл, включающий по крайней мере один атом кислорода или азота, который может быть замещен метилом, или R4 и R5 вместе с атомом углерода, с которым они связаны, представляют собой группу NH.
EA201300122A 2010-07-22 2011-07-01 Циклические n,n'-диарилтиомочевины и n,n'-диарилмочевины - антагонисты андрогеновых рецепторов, противораковое средство, способ получения и применения EA020681B1 (ru)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
RU2010130618/04A RU2434851C1 (ru) 2010-07-22 2010-07-22 Циклические n, n'-диарилтиомочевины или n, n'-диарилмочевины - антагонисты андрогенных рецепторов, противораковое средство, способ получения и применения
PCT/RU2011/000476 WO2012011840A1 (ru) 2010-07-22 2011-07-01 Циклические ν,ν'-диарилтиомочевины и ν,ν'-диарилмочевины - антагонисты андрогеновых рецепторов, противораковое средство, способ получения и применения

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EA201300122A1 true EA201300122A1 (ru) 2013-06-28
EA020681B1 EA020681B1 (ru) 2014-12-30

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US (1) US9073874B2 (ru)
EP (2) EP2597086A4 (ru)
JP (1) JP5897566B2 (ru)
KR (1) KR101738866B1 (ru)
AU (1) AU2011280297B2 (ru)
CA (1) CA2806051C (ru)
CY (1) CY1119184T1 (ru)
DK (1) DK2767531T3 (ru)
EA (1) EA020681B1 (ru)
ES (1) ES2618891T3 (ru)
GE (1) GEP20166450B (ru)
HR (1) HRP20170450T1 (ru)
HU (1) HUE031999T2 (ru)
LT (1) LT2767531T (ru)
PL (1) PL2767531T3 (ru)
PT (1) PT2767531T (ru)
RS (1) RS55876B1 (ru)
RU (1) RU2434851C1 (ru)
SI (1) SI2767531T1 (ru)
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RU2598854C2 (ru) 2011-03-10 2016-09-27 Сучжоу Кинтор Фармасьютикалз, Инк. Производные тиогидантоина, полезные в качестве антагонистов рецептора андрогена
BR112015004637B1 (pt) 2012-09-04 2022-04-05 Shanghai Hengrui Pharmaceutical Co., Ltd. Derivados de imidazolina, seus usos e seus processos de preparação, e composição farmacêutica
CA2889756C (en) 2012-10-26 2023-03-14 Memorial Sloan-Kettering Cancer Center Thiohydantoin compounds as androgen receptor modulators
RU2520134C1 (ru) * 2013-02-27 2014-06-20 Общество с ограниченной ответственностью "Авионко" (ООО "Авионко") Замещенные (r)-3-(4-метилкарбамоил-3-фторфениламино)-тетрагидро-фуран-3-енкарбоновые кислоты и их эфиры, способ их получения и применения
CN104844521B (zh) * 2014-02-13 2017-08-15 成都伊诺达博医药科技有限公司 抗前列腺癌药物恩杂鲁胺的合成方法
CN104844520B (zh) * 2014-02-13 2017-09-05 成都伊诺达博医药科技有限公司 一种合成恩杂鲁胺的方法
RU2557235C1 (ru) * 2014-07-08 2015-07-20 Александр Васильевич Иващенко Замещенные 2-тиоксо-имидазолидин-4-оны и их спироаналоги, противораковый активный компонент, фармацевтическая композиция, лекарственный препарат, способ лечения рака простаты
TWI613194B (zh) * 2015-06-10 2018-02-01 台灣神隆股份有限公司 用於製備恩雜魯胺的新穎方法
TWI726969B (zh) 2016-01-11 2021-05-11 比利時商健生藥品公司 用作雄性激素受體拮抗劑之經取代之硫尿囊素衍生物
CA3124130A1 (en) 2018-12-19 2020-06-25 Celgene Corporation Substituted 3-((3-aminophenyl)amino)piperidine-2,6-dione compounds, compositions thereof, and methods of treatment therewith
WO2020132016A1 (en) 2018-12-19 2020-06-25 Celgene Corporation Substituted 3-((3-aminophenyl)amino)piperidine-2,6-dione compounds, compositions thereof, and methods of treatment therewith
MX2023001823A (es) 2020-08-13 2023-03-13 Pfizer Terapia de combinacion.

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EA020681B1 (ru) 2014-12-30
AU2011280297A1 (en) 2013-03-07
EP2767531B1 (en) 2016-12-21
GEP20166450B (en) 2016-03-25
US9073874B2 (en) 2015-07-07
RU2434851C1 (ru) 2011-11-27
SI2767531T1 (sl) 2017-04-26
LT2767531T (lt) 2017-04-10
US20130116269A1 (en) 2013-05-09
HUE031999T2 (en) 2017-09-28
UA112161C2 (uk) 2016-08-10
JP2013532657A (ja) 2013-08-19
PT2767531T (pt) 2017-03-23
PL2767531T3 (pl) 2017-08-31
KR101738866B1 (ko) 2017-05-23
RS55876B1 (sr) 2017-08-31
HRP20170450T1 (hr) 2017-05-19
CA2806051A1 (en) 2012-01-26
DK2767531T3 (en) 2017-03-13
CA2806051C (en) 2017-02-14
AU2011280297B2 (en) 2013-11-21
JP5897566B2 (ja) 2016-03-30
KR20130046436A (ko) 2013-05-07
CY1119184T1 (el) 2018-02-14
WO2012011840A1 (ru) 2012-01-26
EP2597086A1 (en) 2013-05-29
ES2618891T3 (es) 2017-06-22
EP2597086A4 (en) 2013-11-06
EP2767531A1 (en) 2014-08-20

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