AR054587A1 - Derivados de quinolina antibacterianos - Google Patents

Derivados de quinolina antibacterianos

Info

Publication number
AR054587A1
AR054587A1 ARP060103260A ARP060103260A AR054587A1 AR 054587 A1 AR054587 A1 AR 054587A1 AR P060103260 A ARP060103260 A AR P060103260A AR P060103260 A ARP060103260 A AR P060103260A AR 054587 A1 AR054587 A1 AR 054587A1
Authority
AR
Argentina
Prior art keywords
alkyl
aryl
het
hydrocarbon radical
carbon atoms
Prior art date
Application number
ARP060103260A
Other languages
English (en)
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 AR054587A1 publication Critical patent/AR054587A1/es

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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)

Abstract

Los compuestos reivindicados son utiles para el tratamiento de enfermedades bacterianas, incluidas las enfermedades micobacterianas, en particular .aquellas enfermedades causadas por micobacterias patogénicas, tales como Mycobacterium tuberculosis, M. bovis, M avium y M. marinum. También se reivindica una composicion que comprende un vehículo farmacéuticamente aceptable y, como ingrediente activo, una cantidad terapéuticamente efectiva de los compuestos reivindicados, el uso de los compuestos o las composiciones reivindicadas para la fabricacion de un medicamento para el tratamiento de enfermedades bacterianas y un proceso para preparar los compuestos reivindicados. Reivindicacion 1: Un compuesto de acuerdo con la formula general (la) o la Formula general (Ib): una de sus sales de adicion ácidas o básicas farmacéuticamente aceptables, una de sus aminas cuaternarias, una de sus formas estereoquímicamente isoméricas, una de sus formas tautoméricas, una de sus formas de N-oxido o una de sus prodrogas, en donde: p es un numero entero igual a 0, 1, 2, 3, o 4; q es un numero entero igual a 1, 2 o 3; Z es un radical seleccionado de las formulas: (a) o (b); R1 es ciano, halo, alquilo, haloalquilo, hidroxi, alquiloxi, alquiltio, alquiloxialquilo, alquiltioalquilo, arilalquilo, di(aril)alquilo, arilo o Het; R2 es hidrogeno, alquiloxi arilo, ariloxi, hidroxi, mercapto, alquiloxialquiloxi, alquiltio, mono o di(alquil)amino, prrolidino o un radical de formula (3) en donde Y es CH2, O, S, NH o N-alquilo; R3 es alquilo, arilalquilo, arilo, mon- o di-alquilaminoalquilo, Het o Het-alquilo; R4 y R5 cada uno independientemente es hidrogeno; alquilo; alquiloxialquilo; arilalquilo; Het- alquilo; mono- o dialquilaminoalquilo; Het; o arilo; o R4 y R5 junto con el átomo de nitrogeno al cual están unidos forman un radical seleccionado del grupo que consiste en pirrolidino, piperidino, piperazino, morfolino, 4-tiomorfolino, 2,3-dihidroisoindol-1-ilo, tiazolidin-3-ilo, 1,2,3,6- tetrahidropirididilo, 1,4-diazacicloheptilo, 1-aza-4-oxacicloheptilo, 1,2,3,4-tetrahidroisoquinolin-2-ilo, 2H- pirrolilo, pirrolinilo, pirrolilo, imidazolidinilo, pirazolidinilo, 2-imidazolinilo, 2-pirazolinilo, imidazolilo, pirazolilo, triazolilo, piridinilo, piridazinilo, pirimidinilo, pirazinilo y triazinilo, opcionalmente sustituido con uno o varios sustituyentes, cada sustituyente independientemente seleccionado de alquilo, haloalquilo, halo, arilalquilo, hidroxi, alquiloxi, amino, mono- o dialquilamino, alquiltio, alquiloxialquilo, alquiltioalquilo, arilo, piridilo o pirimidinilo; R6 es arilo o Het; R7es hidrogeno, halo, alquilo, arilo o Het; R8 es un radical hidrocarbonado saturado lineal o ramificado que tiene entre 1 y 6 átomos de carbono; R9 es hidrogeno o alquilo; R10 es oxo; y X es -CH2- o -CO-; alquilo es un radical hidrocarbonado saturado lineal o ramificado que tiene entre 1 y 6 átomos de carbono; o es un radical hidrocarbonado saturado cíclico que tiene entre 3 y 6 átomos de carbono; o es un radical hidrocarbonado saturado cíclico que tiene entre 3 y 6 átomos de carbono unido a un radical hidrocarbonado saturado lineal o ramificado que tiene entre 1 y 6 átomos de carbono; en donde cada átomo de carbono puede estar opcionalmente sustituido con ciano, hidroxi, alquiloxi u oxo; arilo es un homociclo seleccionado de fenilo, naftilo, acenaftilo o tetrahidronaftilo, en donde cada uno está opcionalmente sustituido con 1, 2 o 3 sustituyentes, en donde cada sustituyente se selecciona independientemente de hidroxi, halo, ciano, nitro, amino, mono- o dialquilamino, alquilo, haloalquilo, alquiloxi, carboxilo, alquiloxicarbonilo, aminocarbonilo, morfolinilo o mono- o dialquilaminocarbonilo; Het es un heterociclo monocíclico seleccionado de N-fenoxiplperidinilo, piperidinilo, pirrolilo, pirazolilo, imidazolilo, furanilo, tienilo, oxazolilo, isoxazolilo, tiazolilo, isotiazolilo, piridinilo, pirimidinilo, pirazinilo o piridazinilo; o un heterociclo bicíclico seleccionado de quinolinilo, quinoxalinilo, indolilo, benzimidazolilo, benzoxazolilo, benzisoxazolilo, benzotiazolilo, benzisotiazolilo, benzofuranilo, benzotienilo, 2,3-dihidrobenzo[1,4]dioxinilo o benzo(1,3]dioxolilo; cada heterociclo monocíclico y bicíclico está opcionalmente sustituido con 1, 2 o 3 sustituyentes, cada sustituyente independientemente seleccionado de halo, hidroxi, alquilo o alquiloxi; halo es un sustituyente seleccionado de fluor, cloro, bromo o yodo; y haloalquilo es un radical hidrocarbonado saturado lineal o ramificado que tiene entre 1 y 6 átomos de carbono o un radical hidrocarbonado saturado cíclico que tiene entre 3 y 6 átomos de carbono o un radical hidrocarbonado saturado cíclico que tiene entre 3 y 6 átomos de carbono unido a un radical hidrocarbonado saturado lineal o ramificado que tiene entre 1 y 6 átomos e C; en donde uno o varios átomos de C están sustituidos con uno o varios átomos de halo.
ARP060103260A 2005-07-28 2006-07-27 Derivados de quinolina antibacterianos AR054587A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP05106962 2005-07-28

Publications (1)

Publication Number Publication Date
AR054587A1 true AR054587A1 (es) 2007-06-27

Family

ID=35610159

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP060103260A AR054587A1 (es) 2005-07-28 2006-07-27 Derivados de quinolina antibacterianos

Country Status (31)

Country Link
US (1) US7915292B2 (es)
EP (1) EP1912948B1 (es)
JP (1) JP5100647B2 (es)
KR (1) KR101334719B1 (es)
CN (1) CN101273016B (es)
AP (1) AP2322A (es)
AR (1) AR054587A1 (es)
AU (1) AU2006274918B2 (es)
BR (1) BRPI0614122B8 (es)
CA (1) CA2614981C (es)
CY (1) CY1117247T1 (es)
DK (1) DK1912948T3 (es)
EA (1) EA015617B1 (es)
ES (1) ES2554924T3 (es)
HK (1) HK1122804A1 (es)
HR (1) HRP20151308T1 (es)
HU (1) HUE026259T2 (es)
IL (1) IL188987A0 (es)
JO (1) JO3077B1 (es)
MX (1) MX2008001219A (es)
MY (1) MY148219A (es)
NO (1) NO341795B1 (es)
NZ (1) NZ565946A (es)
PL (1) PL1912948T3 (es)
PT (1) PT1912948E (es)
RS (1) RS54382B1 (es)
SI (1) SI1912948T1 (es)
TW (1) TWI427065B (es)
UA (1) UA94051C2 (es)
WO (1) WO2007014885A1 (es)
ZA (1) ZA200800783B (es)

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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
DK2841425T3 (en) 2012-04-27 2016-06-27 Janssen Pharmaceutica Nv ANTIBACTERIAL QUINOLIN DERIVATIVES
EA038350B1 (ru) 2012-04-27 2021-08-12 Янссен Фармацевтика Нв Антибактериальные хинолиновые производные
CA2873295A1 (en) * 2012-08-24 2014-02-27 F. Hoffmann-La Roche Ag New bicyclicpyridine derivatives
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

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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
BR9507672A (pt) * 1994-05-24 1997-08-19 Hoffmann La Roche Derivados tricíclicos de dicarbonila
BR9909994A (pt) * 1998-04-29 2000-12-26 Smithkline Beecharm P L C Quinolinas usadas como inibidores de mrs e bactericidas
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
TW200800901A (en) 2008-01-01
WO2007014885A1 (en) 2007-02-08
PT1912948E (pt) 2015-12-21
SI1912948T1 (sl) 2016-01-29
EA200800455A1 (ru) 2008-10-30
BRPI0614122B1 (pt) 2020-09-24
DK1912948T3 (en) 2016-01-18
IL188987A0 (en) 2008-08-07
HUE026259T2 (en) 2016-06-28
NZ565946A (en) 2010-11-26
CY1117247T1 (el) 2017-04-05
EP1912948A1 (en) 2008-04-23
MX2008001219A (es) 2008-03-24
EA015617B1 (ru) 2011-10-31
CN101273016A (zh) 2008-09-24
RS54382B1 (en) 2016-04-28
MY148219A (en) 2013-03-29
AU2006274918B2 (en) 2011-09-22
PL1912948T3 (pl) 2016-02-29
HK1122804A1 (en) 2009-05-29
BRPI0614122B8 (pt) 2023-01-10
JP2009502869A (ja) 2009-01-29
NO341795B1 (no) 2018-01-22
EP1912948B1 (en) 2015-09-09
BRPI0614122A8 (pt) 2019-01-29
NO20081008L (no) 2008-02-27
US20080182855A1 (en) 2008-07-31
US7915292B2 (en) 2011-03-29
JO3077B1 (ar) 2017-03-15
ZA200800783B (en) 2009-06-24
HRP20151308T1 (hr) 2016-01-01
JP5100647B2 (ja) 2012-12-19
AP2322A (en) 2011-11-18
KR20080031973A (ko) 2008-04-11
TWI427065B (zh) 2014-02-21
KR101334719B1 (ko) 2013-11-29
AU2006274918A1 (en) 2007-02-08
CA2614981A1 (en) 2007-02-08
ES2554924T3 (es) 2015-12-28
UA94051C2 (ru) 2011-04-11
BRPI0614122A2 (pt) 2011-03-09
CA2614981C (en) 2014-06-03
CN101273016B (zh) 2013-01-02

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