AR064153A1 - Derivados de quinolina antibacterianos. procesos de obtencion y composiciones farmaceuticas. - Google Patents

Derivados de quinolina antibacterianos. procesos de obtencion y composiciones farmaceuticas.

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Publication number
AR064153A1
AR064153A1 ARP070105446A ARP070105446A AR064153A1 AR 064153 A1 AR064153 A1 AR 064153A1 AR P070105446 A ARP070105446 A AR P070105446A AR P070105446 A ARP070105446 A AR P070105446A AR 064153 A1 AR064153 A1 AR 064153A1
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Argentina
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alkyl
aryl
het
mono
radical
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ARP070105446A
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Janssen Pharmaceutica Nv
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic 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
    • C07D215/16Heterocyclic 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
    • C07D215/20Oxygen atoms
    • C07D215/22Oxygen atoms attached in position 2 or 4
    • C07D215/227Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic 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
    • A61K31/47Quinolines; Isoquinolines
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • A61P31/06Antibacterial agents for tuberculosis
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic 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
    • C07D215/04Heterocyclic 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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic 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
    • C07D215/12Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic 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
    • C07D215/12Heterocyclic 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
    • C07D215/14Radicals substituted by oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic 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
    • C07D215/16Heterocyclic 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
    • C07D215/36Sulfur atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/02Heterocyclic 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
    • C07D401/06Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D407/00Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/04Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic 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
    • C07D413/06Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic 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
    • C07D417/02Heterocyclic 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
    • C07D417/06Heterocyclic 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

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  • 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)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Epidemiology (AREA)
  • Pulmonology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

También se reivindica una composicion que comprende un portador farmacéuticamente aceptable y, como ingrediente activo, una cantidad terapéuticamente efectiva de los compuestos reivindicados, al uso de los compuestos o composiciones reivindicados para la preparacion de un medicamento para el tratamiento de una infeccion bacteriana y a un proceso para preparar los compuestos reivindicados. Reivindicacion 1: Un compuesto de la formula (1a) o (1b) incluyendo cualquiera de sus formas estereoquímicamente isoméricas, en donde Q representa un radical de la formula (2), (3) o (4); p es un numero entero igual a 1, 2, 3 o 4; q es un numero entero igual a cero, 1, 2, 3 o 4; R1 es hidrogeno, ciano, formilo, carboxilo, halo, alquilo, alquenilo C2-6, alquinilo C2-6, haloalquilo, hidroxi, alquiloxi, alquiltio, alquiltioalquilo, -C=N-OR11, amino, mono- o di(alquil)amino, aminoalquilo, mono- o di(alquil)aminoalquilo, alquilcarbonilaminoalquilo, aminocarbonilo, mono- o di(alquil)aminocarbonilo, arilalquilo, arilcarbonilo, R5aR4aNalquilo, di(aril)alquilo, arilo, R5aR4aN-, R5aR4aN-C(=O)-, o Het; R2 es hidrogeno, alquiloxi, arilo, ariloxi, hidroxi, mercapto, alquiloxialquiloxi, alquiltio, mono- o di(alquil)amino, pirrolidino o un radical de formula (2) en donde Y es CH2, O, S, NH o N-alquilo; R3 es alquilo, arilalquilo, aril-O-alquilo, aril-alquil-O-alquilo, arilo, aril-arilo, Het, Het-alquilo, Het-O-alquilo, Het-alquil-O-alquilo o un radical de formula (3); R3a es H, ciano, alquilo, arilalquilo, aril-O-alquilo, aril-alquil-O-alquilo, arilo, aril-arilo, Het, Het-alquilo, Het-O-alquilo, o Het-alquil-O-alquilo; R4 y R5 cada uno es, de modo independiente, hidrogeno; alquilo; alquiloxialquilo; arilalquilo; Het-alquilo; mono- o dialquilaminoalquilo; biciclo[2,2,1]heptilo; Het; arilo; o -C(=NH)-NH2; o R4 y R5 junto con el átomo de nitrogeno al que están unidos forman un radical seleccionado del grupo que consiste en pirrolidino, piperidino, piperazino, morfolino, 4-tiomorfolino, 1,1-dioxido-2-tiomorfolinilo, azetidinilo, 2,3-dihidroisoindol-1-ilo, tiazolidin-3-ilo, 1,2,3,6-tetrahidropiridilo, hexahidro-1H-azepinilo, hexahidro-1H-1,4-diazepinilo, hexahidro-1,4-oxazepinilo, 12,3,4- tetrahidroisoquinolin-2-ilo, 2,5-diazabiciclo[2,2,1]heptilo, pirrolinilo, pirrolilo, imidazolidinilo, pirazolidinilo, 2-imidazolinilo, 2-pirazolinilo, imidazolilo, pirazolilo, triazolilo, piridinilo, piridazinilo, pirimidinilo, pirazinilo y triazinilo, cada radical opcionalmente sustituido con 1 2, 3 o 4 sustituyentes, cada sustituyente seleccionado, de modo independiente, de alquilo, haloalquilo, alquilcarbonilo, halo, arilalquilo, hidroxi, alquiloxi, amino, mono- o dialquilamino, aminoalquilo, mono- o dialquilaminoalquilo, alquiltio, alquiltioalquilo, arilo, piridilo, pirimidinilo, piperidinilo opcionalmente sustituido con alquilo o pirrolidinilo opcionalmente sustituido con arilalquilo; R4a y R5a junto con el átomo de nitrogeno al que 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-tetrahidropiridilo, hexahidro-1H-azepinilo, hexahidro-1H-1,4-diazepinilo, hexahidro-1,4-oxazepinilo, 1,2,3,4-tetrahidroisoquinolin-2-ilo, pirrolinilo, pirrolilo, imidazolidinilo, pirazolidinilo, 2-imidazolinilo, 2-pirazolinilo, imidazolilo, pirazolilo, triazolilo, piridinilo, piridazinilo, pirimidinilo, pirazinilo y triazinilo, cada radical opcionalmente sustituido con 1, 2, 3 o 4 sustituyentes, cada sustituyente seleccionado, de modo independiente, de alquilo, haloalquilo, halo, arilalquilo, hidroxi, alquiloxi, amino, mono- o dialquilamino, alquiltio, alquiltioalquilo, arilo, piridilo o pirimidinilo; R6 es arilo1 o Het; R7 es hidrogeno, halo, alquilo, arilo o Het; R8 es hidrogeno o alquilo; R9 es oxo; o R8 y R9 forman juntos el radical -CH=CH-N=; R11 es hidrogeno o alquilo; arilo es un homociclo seleccionado de fenilo, naftilo, acenaftilo o tetrahidronaftilo, cada uno opcionalmente sustituido con 1, 2 o 3 sustituyentes, estando cada sustituyente seleccionado, de modo independiente, de hidroxi, halo, ciano, nitro, amino, mono- o dialquilamino, alquilo, alquenilo C2-6 opcionalmente sustituido con fenilo, haloalquilo, alquiloxi, haloalquiloxi, carboxilo, alquiloxicarbonilo, aminocarbonilo, morfolinilo o mono- o dialquilaminocarbonilo; arilo1 es un homociclo seleccionado de fenilo, naftilo, acenaftilo o tetrahidronaftilo, cada uno opcionalmente sustituido con 1, 2 o 3 sustituyentes, estando cada sustituyente seleccionado en modo independiente, de hidroxi, halo, ciano, nitro, amino, mono- o dialquilamino, alquilo, haloalquilo, alquiloxi, alquiltio, haloalquiloxi, carboxilo, alquiloxicarbonilo, aminocarbonilo, morfolinilo, Het o mono- o dialquilaminocarbonilo; Het es un heterociclo monocíclico seleccionado de N-fenoxipiperidinilo, piperidinilo, pirrolilo, pirazolilo, imidazolilo, furanilo, tienilo, oxazolilo, isoxazolilo, tiazolilo, isotiazolilo, piridinilo, pirimidinilo, pirazinilo o piridazinilo; o un heterociclo bicíclico seleccionado de quinolinilo, quinoxalinilo, indolilo, bencimidazolilo, benzoxazolilo, benzisoxazolilo, benzotiazolilo, benzisotiazolilo, benzofuranilo, benzotienilo, 2,3-dihidrobenzo[1,4]dioxinilo o benzo[1,3]dioxolilo; estando cada heterociclo monocíclico y bicíclico opcionalmente sustituido con 1, 2 o 3 sustituyentes, cada sustituyente seleccionado de modo independiente, de halo, hidroxi, alquilo o alquiloxi; uno de sus N-oxidos, una de sus sales farmacéuticamente aceptables o uno de sus solvatos.
ARP070105446A 2006-12-06 2007-12-05 Derivados de quinolina antibacterianos. procesos de obtencion y composiciones farmaceuticas. AR064153A1 (es)

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EP06125546 2006-12-06

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AR064153A1 true AR064153A1 (es) 2009-03-18

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ARP070105446A AR064153A1 (es) 2006-12-06 2007-12-05 Derivados de quinolina antibacterianos. procesos de obtencion y composiciones farmaceuticas.

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US (1) US20100069366A1 (es)
EP (1) EP2099762B1 (es)
JP (1) JP5356244B2 (es)
KR (1) KR101514992B1 (es)
CN (1) CN101547907B (es)
AP (1) AP2478A (es)
AR (1) AR064153A1 (es)
AT (1) ATE467619T1 (es)
AU (1) AU2007328980B2 (es)
BR (1) BRPI0719920B8 (es)
CA (1) CA2668515C (es)
CL (1) CL2007003519A1 (es)
CY (1) CY1111188T1 (es)
DE (1) DE602007006553D1 (es)
DK (1) DK2099762T3 (es)
EA (1) EA200970534A1 (es)
ES (1) ES2345463T3 (es)
HK (1) HK1137441A1 (es)
HR (1) HRP20100428T1 (es)
IL (1) IL199079A (es)
JO (1) JO2684B1 (es)
ME (1) ME01127B (es)
MX (1) MX2009005982A (es)
MY (1) MY145924A (es)
NO (1) NO341996B1 (es)
NZ (1) NZ576863A (es)
PL (1) PL2099762T3 (es)
PT (1) PT2099762E (es)
RS (1) RS51382B (es)
SI (1) SI2099762T1 (es)
TW (1) TWI484959B (es)
UA (1) UA101305C2 (es)
WO (1) WO2008068266A1 (es)
ZA (1) ZA200903947B (es)

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Publication number Priority date Publication date Assignee Title
JP5857511B2 (ja) * 2010-08-10 2016-02-10 住友化学株式会社 植物病害防除組成物およびその用途
ES2607879T3 (es) 2012-04-27 2017-04-04 Janssen Pharmaceutica N.V. Derivados de quinolina antibacterianos
JP6153604B2 (ja) 2012-04-27 2017-06-28 ヤンセン ファーマシューティカ エヌ.ベー. 抗菌性キノリン誘導体
CN105017147B (zh) * 2014-04-30 2019-02-01 中国医学科学院药物研究所 一种回收和利用Bedaquiline立体化学异构体的方法
CN105330595B (zh) * 2014-07-14 2019-12-10 上海嘉坦医药科技有限公司 吡啶衍生物及其作为抗分支杆菌的应用
CA2954872C (en) * 2014-07-14 2019-08-13 Cisen Pharmaceutical Co., Ltd. Pyridine derivatives and anti-mycobacterial use thereof
CN108473428B (zh) * 2016-01-13 2021-07-23 上海嘉坦医药科技有限公司 一种吡啶衍生物类化合物的制备方法及其中间体和晶型
JP6997095B2 (ja) * 2016-03-07 2022-02-03 ザ グローバル アライアンス フォー ティービー ドラッグ デベロップメント, インコーポレイテッド 抗菌性化合物およびその使用
CN109384716B (zh) * 2017-08-11 2021-06-29 海创药业股份有限公司 一种氘代喹啉化合物及其制备和用途

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CA2270123A1 (en) * 1996-10-28 1998-05-07 Department Of The Army, U.S. Government Compounds, compositions and methods for treating antibiotic-resistant infections
DE60332023D1 (de) * 2002-07-25 2010-05-20 Janssen Pharmaceutica Nv Chinolinderivate und deren verwendung als mycobakterielle inhibitoren
KR101150172B1 (ko) * 2004-01-23 2012-05-25 얀센 파마슈티카 엔.브이. 치환된 퀴놀린 및 마이코박테리아 저해제로서의 용도
ATE444068T1 (de) * 2004-01-23 2009-10-15 Janssen Pharmaceutica Nv Chinolinderivate und ihre verwendung als mycobakterielle inhibitoren
MXPA06008596A (es) * 2004-01-29 2006-08-28 Janssen Pharmaceutica Nv Derivados de quinolina para uso como inhibidores micobacterianos.
PT1753427E (pt) * 2004-05-28 2008-07-04 Janssen Pharmaceutica Nv Utilização de derivados quinolina substituídos para o tratamento de doenças micobacterianas resistentes a fármacos
EP1677083A1 (fr) * 2004-12-22 2006-07-05 Roxer Industries S.A. Capteur de niveau d'un liquide.
EE05697B1 (et) * 2005-06-08 2014-02-17 Janssen Pharmaceutica N.V. Kinoliini derivaadid kui antibakteriaalsed toimeained

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HRP20100428T1 (hr) 2010-09-30
MY145924A (en) 2012-05-15
DE602007006553D1 (de) 2010-06-24
RS51382B (en) 2011-02-28
JP5356244B2 (ja) 2013-12-04
ZA200903947B (en) 2010-08-25
BRPI0719920B1 (pt) 2020-08-04
ATE467619T1 (de) 2010-05-15
AU2007328980A1 (en) 2008-06-12
AP2478A (en) 2012-09-27
KR20090090360A (ko) 2009-08-25
ME01127B (me) 2013-03-20
PL2099762T3 (pl) 2010-10-29
EP2099762B1 (en) 2010-05-12
UA101305C2 (ru) 2013-03-25
HK1137441A1 (en) 2010-07-30
EP2099762A1 (en) 2009-09-16
NO341996B1 (no) 2018-03-12
AP2009004872A0 (en) 2009-06-30
TW200840575A (en) 2008-10-16
CY1111188T1 (el) 2015-06-11
TWI484959B (zh) 2015-05-21
MX2009005982A (es) 2009-06-16
SI2099762T1 (sl) 2010-09-30
JO2684B1 (en) 2013-03-03
CA2668515C (en) 2016-03-29
AU2007328980B2 (en) 2013-04-18
US20100069366A1 (en) 2010-03-18
NZ576863A (en) 2011-09-30
BRPI0719920B8 (pt) 2021-05-25
CN101547907B (zh) 2013-01-02
JP2010511667A (ja) 2010-04-15
EA200970534A1 (ru) 2009-10-30
IL199079A (en) 2013-06-27
PT2099762E (pt) 2010-08-04
BRPI0719920A2 (pt) 2014-03-04
KR101514992B1 (ko) 2015-04-24
CN101547907A (zh) 2009-09-30
WO2008068266A1 (en) 2008-06-12
DK2099762T3 (da) 2010-08-30
ES2345463T3 (es) 2010-09-23
CA2668515A1 (en) 2008-06-12
CL2007003519A1 (es) 2008-07-11
NO20092539L (no) 2009-09-04

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