WO2013039428A3 - Quinoline derivatives and method for producing and using same - Google Patents

Quinoline derivatives and method for producing and using same Download PDF

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Publication number
WO2013039428A3
WO2013039428A3 PCT/RU2012/000725 RU2012000725W WO2013039428A3 WO 2013039428 A3 WO2013039428 A3 WO 2013039428A3 RU 2012000725 W RU2012000725 W RU 2012000725W WO 2013039428 A3 WO2013039428 A3 WO 2013039428A3
Authority
WO
WIPO (PCT)
Prior art keywords
methoxy
producing
quinoline derivatives
phenylbutan
chloroquinolin
Prior art date
Application number
PCT/RU2012/000725
Other languages
French (fr)
Russian (ru)
Other versions
WO2013039428A2 (en
Inventor
Анна Борисовна НАЗАРЕНКО
Владимир Егорович ФЕДОРОВ
Вадим Егоревич ИЛЬИН
Антон Владимирович ОМЕЛЬКОВ
Евсей Александрович РУЧКО
Original Assignee
Закрытое Акционерное Общество "Фарм-Синтез"
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 Закрытое Акционерное Общество "Фарм-Синтез" filed Critical Закрытое Акционерное Общество "Фарм-Синтез"
Publication of WO2013039428A2 publication Critical patent/WO2013039428A2/en
Publication of WO2013039428A3 publication Critical patent/WO2013039428A3/en

Links

Classifications

    • 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

Landscapes

  • 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

The present invention relates to novel quinoline derivatives, such as substituted 1-(2-chloroquinolin-3-yl)-4-dimethylamino-2-(naphthalen-1-yl)-1- phenylbutan-2-ols, to a method for producing same, and also to the use thereof as antimycobacterial agents, in particular to 5,6,7-substituted 1-(2-chloroquinolin-3-yl)-4-dimethylamino-2-(naphthalen-1-yl)-1- phenylbutan-2-ols of general formula (I), where R1 is Н or methoxy, R2 is Н, methoxy or -O-(CH2)n-O-, R3 is Н, methoxy or -O-(CH2)n-O-, n=1-2, and also to the pharmaceutically acceptable salts thereof with acids which exhibit activity in relation to mycobacteria. The invention also relates to a method for producing compounds of formula (I), which consists in interacting corresponding arylquinolines with an aromatic ketone and using said compounds as an active principle in the creation of anti-tubercular medicinal preparations.
PCT/RU2012/000725 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 WO2013039428A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
RU2011137490 2011-09-12
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
WO2013039428A2 WO2013039428A2 (en) 2013-03-21
WO2013039428A3 true WO2013039428A3 (en) 2013-05-10

Family

ID=47883906

Family Applications (1)

Application Number Title Priority Date Filing Date
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

Country Status (2)

Country Link
RU (1) RU2486175C2 (en)
WO (1) WO2013039428A2 (en)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004011436A1 (en) * 2002-07-25 2004-02-05 Janssen Pharmaceutica N.V. Quinoline derivatives and their use as mycobacterial inhibitors
WO2006125769A1 (en) * 2005-05-25 2006-11-30 Janssen Pharmaceutica N.V. Process for preparing (alpha s, beta r)-6-bromo-alpha-[2-(dimethylamino)ethyl]-2-methoxy-alpha-1-naphthalenyl-beta-phenyl-3-quinolineethanol
RU2006145336A (en) * 2004-05-21 2008-06-27 Чирон Корпорейшн (Us) SUBSTITUTED QUINOLINE DERIVATIVES AS MITOTIC KINESINE INHIBITORS
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

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AP2321A (en) * 2004-01-29 2011-11-16 Janssen Pharmaceutica Nv Quinoline derivatives for use as mycobactrial inhibitor.
JO2725B1 (en) * 2006-12-06 2013-09-15 جانسين فارماسوتيكا ان. في Antibacterial Quinoline Derivatives

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004011436A1 (en) * 2002-07-25 2004-02-05 Janssen Pharmaceutica N.V. Quinoline derivatives and their use as mycobacterial inhibitors
RU2006145336A (en) * 2004-05-21 2008-06-27 Чирон Корпорейшн (Us) SUBSTITUTED QUINOLINE DERIVATIVES AS MITOTIC KINESINE INHIBITORS
WO2006125769A1 (en) * 2005-05-25 2006-11-30 Janssen Pharmaceutica N.V. Process for preparing (alpha s, beta r)-6-bromo-alpha-[2-(dimethylamino)ethyl]-2-methoxy-alpha-1-naphthalenyl-beta-phenyl-3-quinolineethanol
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

Also Published As

Publication number Publication date
RU2011137490A (en) 2013-03-20
RU2486175C2 (en) 2013-06-27
WO2013039428A2 (en) 2013-03-21

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