RS54794B1 - Antibakterijski derivati hinolina - Google Patents

Antibakterijski derivati hinolina

Info

Publication number
RS54794B1
RS54794B1 RS20160374A RSP20160374A RS54794B1 RS 54794 B1 RS54794 B1 RS 54794B1 RS 20160374 A RS20160374 A RS 20160374A RS P20160374 A RSP20160374 A RS P20160374A RS 54794 B1 RS54794 B1 RS 54794B1
Authority
RS
Serbia
Prior art keywords
alkyl
alkyloxy
mono
het
aryl
Prior art date
Application number
RS20160374A
Other languages
English (en)
Inventor
Jérôme Emile Georges Guillemont
David Francis Alain Lançois
Ismet Dorange
Koenraad Jozef Lodewijk Marcel Andries
Anil Koul
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=38126091&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=RS54794(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv
Publication of RS54794B1 publication Critical patent/RS54794B1/sr

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Classifications

    • 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
    • C07D215/20Oxygen 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
    • A61K31/495Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/496Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • 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
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • A61P31/08Antibacterial agents for leprosy
    • 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
    • C07D215/38Nitrogen 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
    • 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
    • C07D413/04Heterocyclic 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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D417/04Heterocyclic 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 directly linked by a ring-member-to-ring-member bond

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Pulmonology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Quinoline Compounds (AREA)

Abstract

Jedinjenje, naznačeno time, što ima formulu (Ia) ili (Ib)uključujući njegove stereohemijski izomerne forme, pri čemuq je ceo broj koji iznosi nula, 1, 2, 3 ili 4;p je ceo broj koji iznosi 1, 2, 3 ili 4;R1 je alkenil, alkinil, -C=N-OR11, amino, mono ili di(alkil)amino, aminoalkil, mono ili di(alkil)aminoalkil, alkilkarbonilaminoalkil, aminokarbonil, mono ili di(alkil)aminokarbonil, arilkarbonil, R5aR4aNalkil, R5aR4aN-, R5aR4aN-C(=O)-;R2 je vodonik, alkiloksi, aril, ariloksi, hidroksi, merkapto, alkiloksialkiloksi, alkiltio, mono ili di(alkil)amino, pirolidino ili radikal formulegde Y je CH2, O, S, NH ili N-alkil;R3 je alkil, arilalkil, aril-O-alkil, aril-alkil-O-alkil, aril, Het, Het-alkil, Het-O-alkil, Het-alkil-O-alkil iliR4 i R5 svaki nezavisno su vodonik, alkil ili benzil; iliR4 i R5 zajedno i uključujući N za koji su vezani mogu da obrazuju radikal koji je izabran iz grupe koja obuhvata pirolidinil, 2-pirolinil, 3-pirolinil, pirolil, imidazolidinil, pirazolidinil, 2-imidazolinil, 2-pirazolinil, imidazolil, pirazolil, triazolil, piperidinil, piridinil, piperazinil, imidazolidinil, piridazinil, pirimidinil, pirazinil, triazinil, morfolinil i tiomorfolinil, pri čemu je svaki radikal opciono supstituisan sa alkilom, halo, haloalkilom, hidroksi, alkiloksi, amino, mono- ili dialkilamino, alkiltio, alkiloksialkilom, alkiltioalkilom i pirimidinilom;R4a i R3a zajedno sa atomom azota za koji su vezani obrazuju radikal koji je izabran iz grupe koja obuhvata pirolidino, piperidino, piperazino, morfolino, 4-tiomorfolino, 2,3-dihidroizoindol-1-il, tiazolidin-3-il, 1,2,3,6-tetrahidropiridil, heksahidro-1H-azepinil, heksahidro-1H-1,4-diazepinil, heksahidro-1,4-oksazepinil, 1,2,3,4-tetrahidroizohinolin-2-il, pirolinil, pirolil, imidazolidinil, pirazolidinil, 2-imidazolinil, 2-pirazolinil, imidazolil, pirazolil, triazolil, piridinil, piridazinil, pirimidinil, pirazinil i triazinil, pri čemu svaki radikal je opciono supstituisan sa 1, 2, 3 ili 4 supstituenta, pri čemu je svaki supstituent nezavisno izabran iz alkila, haloalkila, halo, arilalkila, hidroksi, alkiloksi, amino, mono- ili dialkilamino, alkiltio, alkiltioalkila, arila, piridila ili pirimidinila;R6 je aril1 ili Het;R7 je vodonik, halo, alkil, aril ili Het;R8 je vodonik ili alkil;R9 je okso; iliR8 i R9 zajedno obrazuju radikal -CH=CH-N=;R11 je vodonik ili alkil;aril je homociklično jedinjenje izabrano iz fenila, naftila, acenaftila ili tetrahidronaftila, pri čemu je svaki opciono supstituisan sa 1, 2 ili 3 supstituenta, od kojih je svaki supstituent nezavisno izabran iz hidroksi, halo, cijano, nitro, amino, mono- ili dialkilamino, alkila, haloalkila, alkiloksi, haloalkiloksi, karboksila, alkiloksikarbonila, aminokarbonila, morfolinila ili mono- ili dialkilaminokarbonila;aril1 je homociklično jedinjenje izabrano iz fenila, naftila, acenaftila ili tetrahidronaftila, od kojih je svaki opciono supstituisan sa 1, 2 ili 3 supstituenta, pri čemu je svaki supstituent nezavisno izabran iz hidroksi, halo, cijano, nitro, amino, mono- ili dialkilamino, alkila, haloalkila, alkiloksi, alkiltio, haloalkiloksi, karboksila, alkiloksikarbonila, aminokarbonila, morfolinila, Het ili mono- ili dialkilaminokarbonila;Het je monociklično heterociklično jedinjenje koje je izabrano iz N-fenoksipiperidinila, piperidinila, pirolila, pirazolila, imidazolila, furanila, tienila, oksazolila, izoksazolila, tiazolila, izotiazolila, piridinila, pirimidinila, pirazinila ili piridazinila; ili biciklično heterociklično jedinjenje izabrano iz hinolinila, hinoksalinila, indolila, benzimidazolila, benzoksazolila, benzizoksazolila, benzotiazolila, benzizotiazolila, benzofuranila, benzotienila, 2,3-dihidrobenzo[1,4]dioksinila ili benzo[1,3]dioksolila; pri čemu je svako monociklično i biciklično heterociklično jedinjenje opciono supstituisano sa 1, 2 ili 3 supstituenta, od kojih je svaki nezavisno izabran iz halo, hidroksi, alkila ili alkiloksi;i njegovi N-oksidi, farmaceutski prihvatljive soli ili solvati.Prijava sadrži još 24 patentna zahteva.
RS20160374A 2006-12-06 2007-12-04 Antibakterijski derivati hinolina RS54794B1 (sr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP06125499 2006-12-06
PCT/EP2007/063313 WO2008068267A1 (en) 2006-12-06 2007-12-04 Antibacterial quinoline derivatives
EP07847811.2A EP2099758B1 (en) 2006-12-06 2007-12-04 Antibacterial quinoline derivatives

Publications (1)

Publication Number Publication Date
RS54794B1 true RS54794B1 (sr) 2016-10-31

Family

ID=38126091

Family Applications (1)

Application Number Title Priority Date Filing Date
RS20160374A RS54794B1 (sr) 2006-12-06 2007-12-04 Antibakterijski derivati hinolina

Country Status (33)

Country Link
US (1) US8415475B2 (sr)
EP (1) EP2099758B1 (sr)
JP (1) JP5466011B2 (sr)
KR (1) KR101490222B1 (sr)
CN (2) CN101553470A (sr)
AP (1) AP2479A (sr)
AR (1) AR064151A1 (sr)
AU (1) AU2007328887B2 (sr)
BR (1) BRPI0720220B8 (sr)
CA (1) CA2669819C (sr)
CL (1) CL2007003514A1 (sr)
CY (1) CY1117766T1 (sr)
DK (1) DK2099758T3 (sr)
EA (1) EA016733B1 (sr)
ES (1) ES2573689T3 (sr)
HK (1) HK1208437A1 (sr)
HR (1) HRP20160585T1 (sr)
HU (1) HUE028769T2 (sr)
IL (1) IL199083A (sr)
JO (1) JO3271B1 (sr)
ME (1) ME02498B (sr)
MX (1) MX2009005978A (sr)
MY (1) MY181645A (sr)
NO (1) NO341983B1 (sr)
NZ (1) NZ576823A (sr)
PL (1) PL2099758T3 (sr)
PT (1) PT2099758E (sr)
RS (1) RS54794B1 (sr)
SI (1) SI2099758T1 (sr)
TW (1) TWI406659B (sr)
UA (1) UA100972C2 (sr)
WO (1) WO2008068267A1 (sr)
ZA (1) ZA200903950B (sr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013160431A1 (en) 2012-04-27 2013-10-31 Janssen Pharmaceutica Nv Antibacterial quinoline derivatives
EP2841425B1 (en) 2012-04-27 2016-03-23 Janssen Pharmaceutica, N.V. Antibacterial quinoline derivatives
EP2909192B1 (en) 2012-10-16 2017-05-17 Janssen Pharmaceutica NV Methylene linked quinolinyl modulators of ror-gamma-t
JP6250686B2 (ja) 2012-10-16 2017-12-20 ヤンセン ファーマシューティカ エヌ.ベー. Rorγtのヘテロアリール結合させたキノリニルモジュレータ
CN105073729A (zh) 2012-10-16 2015-11-18 詹森药业有限公司 RORγt的苯基连接的喹啉基调节剂
US10555941B2 (en) 2013-10-15 2020-02-11 Janssen Pharmaceutica Nv Alkyl linked quinolinyl modulators of RORγt
US9221804B2 (en) 2013-10-15 2015-12-29 Janssen Pharmaceutica Nv Secondary alcohol quinolinyl modulators of RORγt
CA2926339A1 (en) 2013-10-15 2015-04-23 Janssen Pharmaceutica Nv Alkyl linked quinolinyl modulators of roryt
US9328095B2 (en) 2013-10-15 2016-05-03 Janssen Pharmaceutica Nv Heteroaryl linked quinolinyl modulators of RORgammat
US9284308B2 (en) 2013-10-15 2016-03-15 Janssen Pharmaceutica Nv Methylene linked quinolinyl modulators of RORγt
US9403816B2 (en) 2013-10-15 2016-08-02 Janssen Pharmaceutica Nv Phenyl linked quinolinyl modulators of RORγt
EP3057422B1 (en) 2013-10-15 2019-05-15 Janssen Pharmaceutica NV Quinolinyl modulators of ror(gamma)t
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
EP3170810B1 (en) * 2014-07-14 2018-09-19 Cisen Pharmaceutical Co., Ltd. Pyridine derivatives and anti-mycobacterial use thereof
EP3250182B1 (en) * 2015-01-27 2023-04-26 Janssen Pharmaceutica NV Dispersible compositions
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
CN105601566A (zh) * 2016-02-02 2016-05-25 张敏 一种护理烧伤后感染的药物组合物
BR122023025283A2 (pt) * 2016-03-07 2024-02-20 The Global Alliance For Tb Drug Dev Inc Compostos antibacterianos e seus usos
WO2018048882A1 (en) 2016-09-06 2018-03-15 The Research Foundation For The State University Of New York Positron imaging tomography imaging agent composition and method for bacterial infection
WO2019145919A1 (en) * 2018-01-29 2019-08-01 Cadila Healthcare Limited Heterocyclic compounds useful as antibacterial agents
CA3198350A1 (en) * 2020-10-22 2022-04-28 Lunella Biotech, Inc. Mitochondrial atp inhibitors targeting the gamma subunit prevent metastasis
WO2023178035A1 (en) 2022-03-14 2023-09-21 Slap Pharmaceuticals Llc Multicyclic compounds

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US5965572A (en) 1996-10-28 1999-10-12 The United States Of America As Respresented By The Secretary Of The Army Methods for treating antibiotic-resistant infections
CN1325475C (zh) * 2002-07-25 2007-07-11 詹森药业有限公司 喹啉衍生物及其作为分枝杆菌抑制剂的应用
WO2005070430A1 (en) 2004-01-23 2005-08-04 Janssen Pharmaceutica N.V. Quinoline derivatives and use thereof as mycobacterial inhibitors
BRPI0507076B8 (pt) 2004-01-23 2021-05-25 Janssen Pharmaceutica Nv quinolinas substituídas, seu processo de preparação, composição farmacêutica que as compreende e seu uso como inibidores micobacterianos
EP1713776B1 (en) * 2004-01-29 2008-05-14 Janssen Pharmaceutica N.V. Quinoline derivatives for use as mycobacterial inhibitors
SI1753427T1 (sl) * 2004-05-28 2008-10-31 Janssen Pharmaceutica Nv Uporaba substituiranih kinolinskih derivatov za zdravljenje na zdravila odpornih mikobakterijskih bolezni
RU2418001C2 (ru) 2004-09-28 2011-05-10 Янссен Фармацевтика Н.В. Домен связывания бактериальной атр-синтазы
EE05394B1 (et) 2004-12-24 2011-04-15 Janssen Pharmaceutica N.V. Kinoliinihendid kasutamiseks latentse tuberkuloosi ravis
EE05697B1 (et) * 2005-06-08 2014-02-17 Janssen Pharmaceutica N.V. Kinoliini derivaadid kui antibakteriaalsed toimeained
JO2837B1 (en) * 2005-08-03 2014-09-15 جانسن فارمسيتكا ان في Quinoline derivatives acting as antibacterial agents
JO2952B1 (en) * 2005-08-03 2016-03-15 جانسين فارماسوتيكا ان. في Quinoline derivatives acting as antibacterial agents
JO2855B1 (en) * 2005-08-03 2015-03-15 شركة جانسين فارماسوتيكا ان. في Quinoline derivatives acting as antibacterial agents

Also Published As

Publication number Publication date
AU2007328887B2 (en) 2013-01-17
IL199083A (en) 2014-08-31
CN101553470A (zh) 2009-10-07
TW200838528A (en) 2008-10-01
EP2099758B1 (en) 2016-03-09
CL2007003514A1 (es) 2008-07-11
ZA200903950B (en) 2010-08-25
NO341983B1 (no) 2018-03-05
HRP20160585T1 (hr) 2016-06-17
KR20090086604A (ko) 2009-08-13
EP2099758A1 (en) 2009-09-16
KR101490222B1 (ko) 2015-02-05
WO2008068267A1 (en) 2008-06-12
US8415475B2 (en) 2013-04-09
AU2007328887A1 (en) 2008-06-12
EA016733B1 (ru) 2012-07-30
ME02498B (me) 2017-02-20
BRPI0720220B1 (pt) 2020-06-09
DK2099758T3 (en) 2016-06-13
JP5466011B2 (ja) 2014-04-09
TWI406659B (zh) 2013-09-01
MY181645A (en) 2020-12-30
BRPI0720220A2 (pt) 2013-12-24
JO3271B1 (ar) 2018-09-16
CY1117766T1 (el) 2017-05-17
NO20092542L (no) 2009-08-25
IL199083A0 (en) 2010-03-28
UA100972C2 (ru) 2013-02-25
HK1208437A1 (en) 2016-03-04
HUE028769T2 (en) 2017-01-30
US20100048566A1 (en) 2010-02-25
CN104744361A (zh) 2015-07-01
BRPI0720220B8 (pt) 2021-05-25
JP2010511668A (ja) 2010-04-15
CA2669819A1 (en) 2008-06-12
AP2479A (en) 2012-09-27
ES2573689T3 (es) 2016-06-09
NZ576823A (en) 2012-01-12
EA200970535A1 (ru) 2009-10-30
AP2009004874A0 (en) 2009-06-30
CA2669819C (en) 2016-08-30
CN104744361B (zh) 2021-06-08
SI2099758T1 (sl) 2016-07-29
MX2009005978A (es) 2009-06-16
PL2099758T3 (pl) 2016-08-31
AR064151A1 (es) 2009-03-18
PT2099758E (pt) 2016-06-02

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