HRP20151308T1 - Antibakterijski derivati kinolina - Google Patents

Antibakterijski derivati kinolina Download PDF

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HRP20151308T1
HRP20151308T1 HRP20151308TT HRP20151308T HRP20151308T1 HR P20151308 T1 HRP20151308 T1 HR P20151308T1 HR P20151308T T HRP20151308T T HR P20151308TT HR P20151308 T HRP20151308 T HR P20151308T HR P20151308 T1 HRP20151308 T1 HR P20151308T1
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methyl
phenyl
quinolin
benzyl
alkyl
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HRP20151308TT
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J.E.G. Guillemont
D.F.A. Lançois
E.T.J. Pasquier
K.J.L.M. Andries
Anil Koul
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Janssen Pharmaceutica Nv
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Publication of HRP20151308T1 publication Critical patent/HRP20151308T1/hr

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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
    • 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
    • A61K31/47042-Quinolinones, e.g. carbostyril
    • 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
    • A61K31/472Non-condensed isoquinolines, e.g. papaverine
    • A61K31/4725Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
    • 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • C07D215/16Heterocyclic 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
    • C07D215/48Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • 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
    • C07D401/04Heterocyclic 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
    • 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
    • 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
    • C07D401/12Heterocyclic 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
    • 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
    • C07D401/14Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic 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
    • C07D405/02Heterocyclic 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
    • C07D405/06Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic 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
    • C07D405/02Heterocyclic 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
    • C07D405/12Heterocyclic 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
    • 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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  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Quinoline Compounds (AREA)

Claims (11)

1. Spoj prema općoj Formuli (Ia) ili Formuli (Ib):  [image] [image] njegova farmaceutski prihvatljiva kisela ili bazična adicijska sol, njegov kvarterni amin, njegov stereokemijski izomerni oblik, njegov tautomerni oblik ili njegov N-oksidni oblik, naznačen time da: p je cijeli broj jednak nula, 1, 2, 3 ili 4; q je cijeli broj jednak 1, 2 ili 3; Z je radikal odabran od formula: [image] R1 je cijano, halo, alkil, haloalkil, hidroksi, alkiloksi, alkiltio, alkiloksialkil, alkiltioalkil, arilalkil, di(aril)alkil, aril ili Het; R2 je vodik, alkiloksi, aril, ariloksi, hidroksi, merkapto, alkiloksialkiloksi, alkiltio, mono ili di(alkil)amino, pirolidino ili radikal s formulom  [image] pri čemu Y je CH2, O, S, NH ili N-alkil ; R3 je alkil, arilalkil, aril, mono- ili di-alkilaminoalkil, Het ili Het-alkil; R4 i R5 svaki neovisno je vodik; alkil; alkiloksialkil; arilalkil; Het-alkil; mono- ili dialkilaminoalkil; Het; ili aril; ili R4 i R5 zajedno s dušikovim atomom na koji su vezani tvore radikal odabran iz skupine koja sadrži pirolidino, piperidino, piperazino, morfolino, 4-tiomorfolino, 2,3-dihidroizoindol-1-il, tiazolidin-3-il, 1,2,3,6-tetrahidropiridil, 1,4-diazacikloheptil, 1-aza-4-oksacikloheptil, 1,2,3,4-tetrahidroizokinolin-2-il, 2H-pirolil, pirolinil, pirolil, imidazolidinil, pirazolidinil, 2-imidazolinil, 2-pirazolinil, imidazolil, pirazolil, triazolil, piridinil, piridazinil, pirimidinil, pirazinil i triazinil, proizvoljno supstituiran s jednim ili više supstituenata, a svaki supstituent je neovisno odabran od alkila, haloalkila, halo, arilalkila, hidroksi, alkiloksi, amino, mono- ili dialkilamino, alkiltio, alkiloksialkila, alkiltioalkila, arila, piridila ili pirimidinila; R6 je aril ili Het; R7 je vodik, halo, alkil, aril ili Het; R8 je ravni ili razgranati zasićeni radikal ugljikovodika koji ima od 1 do 6 ugljikovih atoma; R9 je vodik ili alkil; R10 je okso; i X je -CH2- ili -CO-; alkil je ravni ili razgranati zasićeni radikal ugljikovodika koji ima od 1 do 6 ugljikovih atoma; ili je ciklički zasićeni radikal ugljikovodika koji ima od 3 do 6 ugljikovih atoma; ili je ciklički zasićeni radikal ugljikovodika koji ima od 3 do 6 ugljikovih atoma vezanih na ravni ili razgranati zasićeni radikal ugljikovodika koji ima od 1 do 6 ugljikovih atoma; pri čemu svaki ugljikov atom može biti proizvoljno supstituiran s cijano, hidroksi, alkiloksi ili okso; aril je homocikal odabran od fenila, naftila, acenaftila ili tetrahidronaftila, koji je svaki proizvoljno supstituiran s 1, 2 ili 3 supstituenata, te je svaki supstituent neovisno odabran od hidroksi, halo, cijano, nitro, amino, mono- ili dialkilamino, alkila, haloalkila, alkiloksi, karboksila, alkiloksikarbonila, aminokarbonila, morfolinila ili mono- ili dialkilaminokarbonila; Het je monociklički heterocikal odabran od N-fenoksipiperidinila, piperidinila, pirolila, pirazolila, imidazolila, furanila, tienila, oksazolila, izoksazolila, tiazolila, izotiazolila, piridinila, pirimidinila, pirazinila ili piridazinila; ili biciklički heterocikal odabran od kinolinila, kinoksalinila, indolila, benzimidazolila, benzoksazolila, benzizoksazolila, benzotiazolila, benzizotiazolila, benzofuranila, benzotienila, 2,3-dihidrobenzo[1,4]dioksinila ili benzo[1,3]dioksolila; svaki monociklički i biciklički heterocikal je proizvoljno supstituiran s 1, 2 ili 3 supstituenata, te je svaki supstituent neovisno odabran od halo, hidroksi, alkila ili alkiloksi; halo je supstituent odabran od fluoro, kloro, bromo ili jodo; i haloalkil je ravni ili razgranati zasićeni radikal ugljikovodika koji ima od 1 do 6 ugljikovih atoma ili ciklički zasićeni radikal ugljikovodika koji ima od 3 do 6 ugljikovih atoma ili ciklički zasićeni radikal ugljikovodika koji ima od 3 do 6 ugljikovih atoma vezanih na ravni ili razgranati zasićeni radikal ugljikovodika koji ima od 1 do 6 ugljikovih atoma; pri čemu su jedan ili više ugljikovih atoma supstituirani s jednim ili više halo atoma.
2. Spoj prema zahtjevu 1, naznačen time da p je 0 ili 1; R1 je halo ili alkil; R2 je alkiloksi ili aril; R3 je aril, arilalkil ili Het-alkil; q je 1; R4 i R5 svaki neovisno su alkil ili R4 i R5zajedno s dušikovim atomom na koji su vezani tvore 4-tiomorfolino, piperidino ili piperazino radikal supstituiran s alkilom ili arilalkilom; R6 je aril proizvoljno supstituiran sa halo, ili R6 je benzofuranil; R7 je vodik; i R8 je ravni ili razgranati zasićeni radikal ugljikovodika koji ima od 1 do 4 ugljikovih atoma.
3. Spoj prema bilo kojem od zahtjeva 1 i 2, naznačen time da p je 1; Z je radikal s formulom (a); R1 je bromo ili metil; R2 je metiloksi ili fenil; R3 je fenil proizvoljno supstituiran s metiloksi, ili benzilom; q je 1; R4 i R5 su svaki metil, etil ili izopropil, ili R4 i R5 zajedno s dušikovim atomom na koji su vezani tvore 4-tiomorfolino radikal, piperidino radikal supstituiran s metilom na 4-položaju ili piperazino radikal supstituiran s benzilom na 4-položaju; R6 je fenil ili benzofuranil; i R7 je vodik.
4. Spoj prema zahtjevu 2, naznačen time da p je 0 ili l; R1 je bromo ili metil; R2 je metiloksi ili fenil; R3 je fenil, benzil ili kinolin-5-ilmetil; q je 1; R4 i R5 su svaki metil ili R4 i R5zajedno s dušikovim atomom na koji su vezani tvore piperazino radikal supstituiran s metilom na 4-položaju; R6 je fenil proizvoljno supstituiran s fluoro na 2-položaju; R7 je vodik; i R8 je etil.
5. Spoj naznačen time da je odabran iz skupa koji čine: 2-{benzil-[(6-metil-2-fenil-kinolin-3-il)-fenil-metil]-amino}-N-(4-metil-piperazin-1-il)-acetamid; N-[(6-bromo-2-metoksi-kinolin-3-il)-fenil-metil]-N',N'-dimetil-N-feniletan-1,2-diamin; N-benzil-N-[(6-bromo-2-fenil-kinolin-3-il)-fenil-metil]-N',N'-dimetiletan-1,2-diamin; 2- {benzil-[(6-metil-2-fenil-kinolin-3-il)-fenil-metil]-amino}-1-(4-metil-piperazin-1-il)-etanon; 2-{[(6-bromo-2-metoksi-kinolin-3-il)-fenil-metil]-kinolin-5-ilmetilamino}-1-(4-metil-piperazin-1-il)-etanon; 2-{benzil-[(6-bromo-2-metoksi-kinolin-3-il)-fenil-metil]-amino}-1-(4-metil-piperazin-1-il)-etanon; N-benzil-N-[(6-bromo-2-metoksi-kinolin-3-il)-(2-fluoro-fenil)-metil]-N',N'-dimetil-etan-1,2-diamin; etil ester {benzil-[(6-bromo-2-metoksi-kinolin-3-il)-fenil-metil]-amino}-octene kiseline; i 2-{benzil-[(6-metil-2-fenil-kinolin-3-il)-fenil-metil]-amino}-1-piperidino-1-il-etanon; njihova farmaceutski prihvatljiva kisela ili bazična adicijska sol, njihov kvarterni amin, njihov stereokemijski izomerni oblik, njihov tautomerni oblik ili njihov N-oksidni oblik.
6. Spoj naznačen time da je odabran iz skupa koji čine: 2-{benzil-[(6-metil-2-fenil-kinolin-3-il)-fenil-metil]-amino}-1-(4-benzil-piperazin-1-il)-etanon; N-[(6-bromo-2-metoksi-kinolin-3-il)-fenil-metil]-N-(2-metoksi-fenil)-N',N'-dimetil-etan-1,2-diamin; 2-{benzil-[(6-metil-2-fenil-kinolin-3-il)-fenil-metil]-amino}-N,N-dimetil-acetamid; N-benzil-N-[(6-bromo-2-fenil-kinolin-3-il)-fenil-metil]-N',N'-dimetiletan-1,2-diamin; 2-{benzil-[(6-metil-2-fenil-kinolin-3-il)-fenil-metil]-amino}-1-(4-metil-piperidin-1-il)-etanon; 2-{benzil-[(6-metil-2-fenil-kinolin-3-il)-fenil-metil]-amino}-N,N-dietil-acetamid; 2-{benzil-[(6-bromo-2-fenil-kinolin-3-il)-fenil-metil]-amino}-N,N-dimetil-acetamid; 2-{[benzofuran-2-il-(2-fenil-kinolin-3-il)-metil]-benzil-amino}-N-izopropil-N-metil-acetamid; 2-{benzil-[(6-metil-2-fenil-kinolin-3-il)-fenil-metil]-amino}-1-tiomorfolin-4-il-etanon; i 2-{benzil-[(6-metil-2-fenil-kinolin-3-il)-fenil-metil]-amino}-N-izopropil-N-metil-acetamid; njihova farmaceutski prihvatljiva kisela ili bazična adicijska sol, njihov kvarterni amin, njihov stereokemijski izomerni oblik, njihov tautomerni oblik ili njihov N-oksidni oblik.
7. Spoj prema bilo kojem od zahtjeva 1 do 6 naznačen time da je za uporabu kao lijek.
8. Pripravak naznačen time da sadrži farmaceutski prihvatljiv nosač, te kao aktivni sastojak, terapijski učinkovitu količinu spoja kako je definirano u bilo kojem od zahtjeva 1 do 6.
9. Uporaba spoja prema bilo kojem od zahtjeva 1 do 6 ili pripravka prema zahtjevu 8 naznačena time da je za proizvodnju lijeka za liječenje bakterijske bolesti.
10. Spoj prema bilo kojem od zahtjeva 1 do 6 naznačen time da je za uporabu za liječenje bakterijske bolesti.
11. Kombinacija (a) spoja prema bilo kojem od zahtjeva 1 do 6, te (b) jednog ili više drugih antibakterijskih sredstava, naznačena time da je za uporabu kao lijek.
HRP20151308TT 2005-07-28 2015-12-01 Antibakterijski derivati kinolina HRP20151308T1 (hr)

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EP05106962 2005-07-28
EP06777972.8A EP1912948B1 (en) 2005-07-28 2006-07-26 Antibacterial quinoline derivatives
PCT/EP2006/064656 WO2007014885A1 (en) 2005-07-28 2006-07-26 Antibacterial quinoline derivatives

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HRP20151308T1 true HRP20151308T1 (hr) 2016-01-01

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EP (1) EP1912948B1 (hr)
JP (1) JP5100647B2 (hr)
KR (1) KR101334719B1 (hr)
CN (1) CN101273016B (hr)
AP (1) AP2322A (hr)
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AU (1) AU2006274918B2 (hr)
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US20130065922A1 (en) * 2010-05-21 2013-03-14 Syngenta Crop Protection Llc Novel amides as fungicides
AU2013254674B2 (en) 2012-04-27 2017-02-02 Janssen Pharmaceutica Nv Antibacterial quinoline derivatives
PL2841426T3 (pl) 2012-04-27 2017-03-31 Janssen Pharmaceutica N.V. Przeciwbakteryjne pochodne chinoliny
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

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