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RU2011137490A - Quinoline derivatives, in particular 5,6,7-substituted with 1- (2-chloroquinolin-3-yl) -4-dimethylamino-2- (naphthalen-1-yl) -1-phenylbutane-2-oli, production method and application COMPOUNDS - Google Patents

Quinoline derivatives, in particular 5,6,7-substituted with 1- (2-chloroquinolin-3-yl) -4-dimethylamino-2- (naphthalen-1-yl) -1-phenylbutane-2-oli, production method and application COMPOUNDS Download PDF

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Publication number
RU2011137490A
RU2011137490A RU2011137490/04A RU2011137490A RU2011137490A RU 2011137490 A RU2011137490 A RU 2011137490A RU 2011137490/04 A RU2011137490/04 A RU 2011137490/04A RU 2011137490 A RU2011137490 A RU 2011137490A RU 2011137490 A RU2011137490 A RU 2011137490A
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Russia
Prior art keywords
substituted
methoxy
chloroquinolin
naphthalen
dimethylamino
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RU2011137490/04A
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Russian (ru)
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RU2486175C2 (en
Inventor
Анна Борисовна Назаренко
Владимир Егорович Федоров
Вадим Игоревич Ильин
Антон Владимирович Омельков
Евсей Александрович Ручко
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Закрытое Акционерное Общество "Фарм-Синтез"
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Priority to RU2011137490/04A priority Critical patent/RU2486175C2/en
Priority to PCT/RU2012/000725 priority patent/WO2013039428A2/en
Publication of RU2011137490A publication Critical patent/RU2011137490A/en
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Publication of RU2486175C2 publication Critical patent/RU2486175C2/en

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    • 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
    • C07D215/18—Halogen atoms or nitro radicals
    • 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
    • A61P31/04—Antibacterial agents
    • A61P31/06—Antibacterial agents for tuberculosis
    • 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
    • C07D215/20—Oxygen atoms
    • 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
    • C07D491/04—Ortho-condensed systems
    • C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Pulmonology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

1. Производные хинолина, в частности 5,6,7-замещенные 1-(2-хлорхинолин-3-ил)-4-диметиламино-2-(нафталин-1-ил)-1-фенилбутан-2-олы общей формулы (I):где Rозначает H, метокси, Rозначает H, метокси, -O-(CH)-O-, Rозначает H, метокси, -O-(СН)-O-, n=1-2, или их фармацевтически приемлемые соли с кислотами, обладающие антимикобактериальной активностью.2. Способ получения соединений формулы (I) по п.1 путем взаимодействия замещенных 2-арилметилхинолинов и арилкетонов под действием металлирующих агентов.3. Способ по п.2, отличающийся тем, что в качестве металлирующего агента используют диэтиламид лития.4. Применение соединений по п.1 для лечения инфекционных заболеваний микобактериальной природы, в частности, туберкулеза.1. Derivatives of quinoline, in particular 5,6,7-substituted 1- (2-chloroquinolin-3-yl) -4-dimethylamino-2- (naphthalen-1-yl) -1-phenylbutan-2-ol of the general formula ( I): where R is H, methoxy, R is H, methoxy, -O- (CH) -O-, R is H, methoxy, -O- (CH) -O-, n = 1-2, or their pharmaceutically acceptable salts with acids with antimycobacterial activity. 2. A method for producing compounds of formula (I) according to claim 1 by reacting substituted 2-arylmethylquinolines and arylketones under the action of metalating agents. The method according to claim 2, characterized in that lithium diethylamide is used as the metallizing agent. The use of compounds according to claim 1 for the treatment of infectious diseases of mycobacterial nature, in particular tuberculosis.

Claims (4)

1. Производные хинолина, в частности 5,6,7-замещенные 1-(2-хлорхинолин-3-ил)-4-диметиламино-2-(нафталин-1-ил)-1-фенилбутан-2-олы общей формулы (I):1. Derivatives of quinoline, in particular 5,6,7-substituted 1- (2-chloroquinolin-3-yl) -4-dimethylamino-2- (naphthalen-1-yl) -1-phenylbutan-2-ol of the general formula ( I):
Figure 00000001
Figure 00000001
 где R1 означает H, метокси, R2 означает H, метокси, -O-(CH2)n-O-, R3 означает H, метокси, -O-(СН2)n-O-, n=1-2, или их фармацевтически приемлемые соли с кислотами, обладающие антимикобактериальной активностью.where R 1 means H, methoxy, R 2 means H, methoxy, -O- (CH 2 ) n -O-, R 3 means H, methoxy, -O- (CH 2 ) n -O-, n = 1- 2, or their pharmaceutically acceptable salts with acids having antimycobacterial activity. 2. Способ получения соединений формулы (I) по п.1 путем взаимодействия замещенных 2-арилметилхинолинов и арилкетонов под действием металлирующих агентов.2. A method for producing compounds of formula (I) according to claim 1 by reacting substituted 2-arylmethylquinolines and arylketones under the action of metalating agents. 3. Способ по п.2, отличающийся тем, что в качестве металлирующего агента используют диэтиламид лития.3. The method according to claim 2, characterized in that lithium diethylamide is used as the metallizing agent. 4. Применение соединений по п.1 для лечения инфекционных заболеваний микобактериальной природы, в частности, туберкулеза. 4. The use of compounds according to claim 1 for the treatment of infectious diseases of mycobacterial nature, in particular tuberculosis.
RU2011137490/04A 2011-09-12 2011-09-12 Quinoline derivatives, particularly 5,6,7-substituted 1-(2-chloroquinolin-3-yl)-4-dimethylamino-2-(naphthalen-1-yl)-1-phenylbutan-2-oles, method for preparing and using compounds RU2486175C2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
RU2011137490/04A RU2486175C2 (en) 2011-09-12 2011-09-12 Quinoline derivatives, particularly 5,6,7-substituted 1-(2-chloroquinolin-3-yl)-4-dimethylamino-2-(naphthalen-1-yl)-1-phenylbutan-2-oles, method for preparing and using compounds
PCT/RU2012/000725 WO2013039428A2 (en) 2011-09-12 2012-09-04 Quinoline derivatives, in particular 5,6,7-substituted 1-(2-chloroquinolin-3-yl)- 4-dimethylamino-2-(naphthalen-1-yl)-1-phenylbutan-2-ols, method for producing same and use of said compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
RU2011137490/04A RU2486175C2 (en) 2011-09-12 2011-09-12 Quinoline derivatives, particularly 5,6,7-substituted 1-(2-chloroquinolin-3-yl)-4-dimethylamino-2-(naphthalen-1-yl)-1-phenylbutan-2-oles, method for preparing and using compounds

Publications (2)

Publication Number Publication Date
RU2011137490A true RU2011137490A (en) 2013-03-20
RU2486175C2 RU2486175C2 (en) 2013-06-27

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Publication number Priority date Publication date Assignee Title
DK2301544T3 (en) * 2002-07-25 2013-01-02 Janssen Pharmaceutica Nv Quinoline derivatives as intermediates for mycobacterial inhibitors
ES2306098T3 (en) * 2004-01-29 2008-11-01 Janssen Pharmaceutica Nv QUINOLINE DERIVATIVES FOR USE AS MICOBACTERIA INHIBITORS.
WO2005113507A1 (en) * 2004-05-21 2005-12-01 Novartis Vaccines And Diagnostics Inc. Substituted quinoline derivatives as mitotic kinesin inhibitors
PT1888604E (en) * 2005-05-25 2012-05-28 Janssen Pharmaceutica Nv Process for preparing (alpha s, beta r)-6-bromo-alpha-[2-(dimethylamino)ethyl]-2-methoxy-alpha-1-naphthalenyl-beta-phenyl-3-quinolineethanol
JO2725B1 (en) * 2006-12-06 2013-09-15 جانسين فارماسوتيكا ان. في Antibacterial Quinoline Derivatives
RU2404971C2 (en) * 2008-12-02 2010-11-27 ЗАО "Фарм-Синтез" Novel quinoline derivatives, synthesis method thereof, use thereof in treating mycobacterial infections, pharmaceutical composition based on said derivatives

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