CA2614981C - Antibacterial quinoline derivatives - Google Patents

Antibacterial quinoline derivatives Download PDF

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Publication number
CA2614981C
CA2614981C CA2614981A CA2614981A CA2614981C CA 2614981 C CA2614981 C CA 2614981C CA 2614981 A CA2614981 A CA 2614981A CA 2614981 A CA2614981 A CA 2614981A CA 2614981 C CA2614981 C CA 2614981C
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CA
Canada
Prior art keywords
methyl
phenyl
benzyl
mol
quinolin
Prior art date
Legal status (The legal status 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 status listed.)
Expired - Lifetime
Application number
CA2614981A
Other languages
English (en)
French (fr)
Other versions
CA2614981A1 (en
Inventor
Jerome Emile Georges Guillemont
David Francis Alain Lancois
Elisabeth Therese Jeanne Pasquier
Koenraad Jozef Lodewijk Marcel Andries
Anil Koul
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Janssen Pharmaceutica NV
Original Assignee
Janssen Pharmaceutica NV
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 Janssen Pharmaceutica NV filed Critical Janssen Pharmaceutica NV
Publication of CA2614981A1 publication Critical patent/CA2614981A1/en
Application granted granted Critical
Publication of CA2614981C publication Critical patent/CA2614981C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
    • 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
    • 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
    • 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
    • A61K31/472—Non-condensed isoquinolines, e.g. papaverine
    • A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
    • 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
    • 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
    • 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
    • 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
    • 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
    • C07D215/12—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pulmonology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Quinoline Compounds (AREA)
CA2614981A 2005-07-28 2006-07-26 Antibacterial quinoline derivatives Expired - Lifetime CA2614981C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP05106962.3 2005-07-28
EP05106962 2005-07-28
PCT/EP2006/064656 WO2007014885A1 (en) 2005-07-28 2006-07-26 Antibacterial quinoline derivatives

Publications (2)

Publication Number Publication Date
CA2614981A1 CA2614981A1 (en) 2007-02-08
CA2614981C true CA2614981C (en) 2014-06-03

Family

ID=35610159

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2614981A Expired - Lifetime CA2614981C (en) 2005-07-28 2006-07-26 Antibacterial quinoline derivatives

Country Status (30)

Country Link
US (1) US7915292B2 (enExample)
EP (1) EP1912948B1 (enExample)
JP (1) JP5100647B2 (enExample)
KR (1) KR101334719B1 (enExample)
CN (1) CN101273016B (enExample)
AP (1) AP2322A (enExample)
AR (1) AR054587A1 (enExample)
AU (1) AU2006274918B2 (enExample)
BR (1) BRPI0614122B8 (enExample)
CA (1) CA2614981C (enExample)
CY (1) CY1117247T1 (enExample)
DK (1) DK1912948T3 (enExample)
EA (1) EA015617B1 (enExample)
ES (1) ES2554924T3 (enExample)
HR (1) HRP20151308T1 (enExample)
HU (1) HUE026259T2 (enExample)
IL (1) IL188987A0 (enExample)
JO (1) JO3077B1 (enExample)
MX (1) MX2008001219A (enExample)
MY (1) MY148219A (enExample)
NO (1) NO341795B1 (enExample)
NZ (1) NZ565946A (enExample)
PL (1) PL1912948T3 (enExample)
PT (1) PT1912948E (enExample)
RS (1) RS54382B1 (enExample)
SI (1) SI1912948T1 (enExample)
TW (1) TWI427065B (enExample)
UA (1) UA94051C2 (enExample)
WO (1) WO2007014885A1 (enExample)
ZA (1) ZA200800783B (enExample)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080076924A1 (en) * 2006-06-30 2008-03-27 Patrick Betschmann Piperazines as P2X7 antagonists
WO2011144444A1 (en) * 2010-05-21 2011-11-24 Syngenta Participations Ag Novel amides as fungicides
AU2013254670B2 (en) 2012-04-27 2017-03-30 Janssen Pharmaceutica Nv Antibacterial quinoline derivatives
ES2576491T3 (es) 2012-04-27 2016-07-07 Janssen Pharmaceutica, N.V. Derivados de quinolina antibacterianos
ES2596243T3 (es) * 2012-08-24 2017-01-05 F. Hoffmann-La Roche Ag Nuevos derivados bicíclicos de piridina
CN104650054B (zh) * 2013-11-25 2019-09-13 重庆医药工业研究院有限责任公司 一种抗结核菌的喹啉噻吩芳氧乙胺衍生物
CN105175329B (zh) * 2014-06-10 2017-09-19 重庆圣华曦药业股份有限公司 一种贝达喹啉消旋体的合成路线及方法
US20190321324A1 (en) * 2016-12-30 2019-10-24 Board Of Regents, The University Of Texas System Quaternary amine antibiotic therapeutics
CN110804016B (zh) * 2019-12-05 2022-11-04 福建省微生物研究所 抗结核分枝杆菌的二芳基喹啉衍生物
US20240287022A1 (en) * 2021-06-28 2024-08-29 Merck Sharp & Dohme Llc Il4i1 inhibitors and methods of use
CN117843568A (zh) * 2024-01-03 2024-04-09 中国药科大学 一种芳烷基取代-1-甲基喹啉季铵盐类衍生物及其制备方法和用途
CN119666810A (zh) * 2025-02-19 2025-03-21 吉林国际旅行卫生保健中心(长春海关口岸门诊部) 基于图像处理的舌拭子样本荧光检测结核分歧杆菌的方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU1041035A3 (ru) * 1982-02-25 1983-09-07 Киорин Сейяку Кабусики Кайся (Фирма) Способ получени производных хинолинкарбоновой кислоты,их гидратов или солей
JPS6463518A (en) * 1987-09-02 1989-03-09 Otsuka Pharma Co Ltd Antiarrhythmic agent
US5235054A (en) * 1992-07-15 1993-08-10 Pfizer Inc. 3-carboxaldehyde substituted quinolines and naphthyridines
DE69518075T2 (de) * 1994-05-24 2001-03-22 F. Hoffmann-La Roche Ag, Basel Tricyclische dicarbonylderivate
CN1307565A (zh) * 1998-04-29 2001-08-08 史密丝克莱恩比彻姆有限公司 用作mrs抑制剂和杀菌剂的喹诺酮化合物
SI1527050T1 (sl) 2002-07-25 2010-08-31 Janssen Pharmaceutica Nv Kinolinski derivati in njihova uporaba kot mikobakterijski inhibitorji

Also Published As

Publication number Publication date
HK1122804A1 (en) 2009-05-29
TWI427065B (zh) 2014-02-21
MX2008001219A (es) 2008-03-24
DK1912948T3 (en) 2016-01-18
IL188987A0 (en) 2008-08-07
US20080182855A1 (en) 2008-07-31
EP1912948A1 (en) 2008-04-23
PL1912948T3 (pl) 2016-02-29
BRPI0614122B8 (pt) 2023-01-10
KR20080031973A (ko) 2008-04-11
NO341795B1 (no) 2018-01-22
SI1912948T1 (sl) 2016-01-29
ZA200800783B (en) 2009-06-24
HUE026259T2 (en) 2016-06-28
CN101273016B (zh) 2013-01-02
CA2614981A1 (en) 2007-02-08
AP2322A (en) 2011-11-18
AU2006274918A1 (en) 2007-02-08
US7915292B2 (en) 2011-03-29
HRP20151308T1 (hr) 2016-01-01
AR054587A1 (es) 2007-06-27
EA200800455A1 (ru) 2008-10-30
NZ565946A (en) 2010-11-26
CN101273016A (zh) 2008-09-24
JP2009502869A (ja) 2009-01-29
AU2006274918B2 (en) 2011-09-22
JO3077B1 (ar) 2017-03-15
MY148219A (en) 2013-03-29
ES2554924T3 (es) 2015-12-28
BRPI0614122A2 (pt) 2011-03-09
EA015617B1 (ru) 2011-10-31
JP5100647B2 (ja) 2012-12-19
BRPI0614122A8 (pt) 2019-01-29
PT1912948E (pt) 2015-12-21
NO20081008L (no) 2008-02-27
TW200800901A (en) 2008-01-01
WO2007014885A1 (en) 2007-02-08
UA94051C2 (ru) 2011-04-11
CY1117247T1 (el) 2017-04-05
KR101334719B1 (ko) 2013-11-29
EP1912948B1 (en) 2015-09-09
BRPI0614122B1 (pt) 2020-09-24
RS54382B1 (sr) 2016-04-28

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Effective date: 20250127