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DK2731608T3 - Inhibitorer for det bakterielle type III sekretionssystem - Google Patents

Inhibitorer for det bakterielle type III sekretionssystem Download PDF

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Publication number
DK2731608T3
DK2731608T3 DK12812134.0T DK12812134T DK2731608T3 DK 2731608 T3 DK2731608 T3 DK 2731608T3 DK 12812134 T DK12812134 T DK 12812134T DK 2731608 T3 DK2731608 T3 DK 2731608T3
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Prior art keywords
t3ss
aryl
heteroaryl
compound
aromatic
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DK12812134.0T
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English (en)
Inventor
Donald T Moir
Daniel Aiello
Norton P Peet
John D Williams
Matthew Torhan
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Microbiotix Inc
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Publication of DK2731608T3 publication Critical patent/DK2731608T3/da

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
    • A61K31/36—Compounds containing methylenedioxyphenyl groups, e.g. sesamin
    • 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
    • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
    • A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
    • 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
    • A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/4355—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having oxygen as a ring hetero atom
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/443—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with oxygen as a ring hetero atom
    • 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
    • A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
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  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)

Claims (15)

1. Bakteriel type III sekretionssystem (T3SS) inhibitor-forbindelse med formlen I:
formel I hvor A er uafhængigt CH eller N; X er uafhængigt valgt blandt hydrogen eller halogen; Z er O, S, NH; eller NR3, hvor R3 er alkyl; Ver NR2, O, eller CR3R4; R2, R3 og R4 er uafhængigt hydrogen eller alkyl; Y er valgt blandt: en divalent lige-kædet, forgrenet, eller cyclisk alkyl-, alkenyl- eller alkynyl-radikal med fra 1 til 6 carbonatomer, som kan indeholde ét eller flere heteroatomer, og som kan være usubstitueret eller substitueret med op til fire substituenter valgt blandt halogen, cyano, hydroxy, amino, alkylamino, carboxyl, alkoxycarbonyl, carboxamido, acylamino, amidino, sulfonamido, aminosulfonyl, alkylsulfonyl, aryl, heteroaryl, alkoxy, alkylthio, aryloxy og heteroaryloxy; oxygen; eller NR5, hvor R5 er hydrogen eller alkyl; W er en aryl- eller heteroaryl-radikal, som danner en fem-leddet eller seks-leddet ring, som yderligere kan være kondenseret med fra 1 til 3 aryl-, heteroaryl-, cycloalkyl- eller heterocycloalkyl-ringe, hvilken W-radikal kan være usubstitueret eller substitueret med op til 4 substituenter valgt blandt halogen, cyano, hydroxy, amino, alkylamino, carboxyl, alkoxycarbonyl, carboxamido, acylamino, amidino, sulfonamido, aminosulfonyl, alkylsulfonyl, aryl, heteroaryl, alkoxy, alkylthio, aryloxy og heteroaryloxy, og hvor vilkårlige to substituenter sammen kan danne en aromatisk eller ikke-aromatisk ringstruktur kondenseret med den nævnte aryl- eller heteroaryl-radikal W, hvilke substituenter fundet på W, også eventuelt kan være bundet kovalent til enten Y eller R2, eller såvel Y som R2, for dannelse af heterocycliske eller carbocycliske ringsystemer, hvilke ringsystemer kan være aromatiske heteroaromatiske eller delvis aromatiske.
2. Bakteriel type III sekretionssystem (T3SS) inhibitor-forbindelse ifølge krav 1, hvor forbindelsen har formlen III:
formel III hvor AerCH eller N; X er uafhængigt valgt blandt hydrogen eller halogen; R er hydrogen eller methyl; Y er en divalent lige-kædet, forgrenet, eller cyclisk alkyl-, alkenyl- eller alkynyl-radikal med fra 1 til 6 carbonatomer, som kan indeholde ét eller flere heteroatomer, og som kan være usubstitueret eller substitueret med op til fire substituenter valgt blandt halogen, cyano, hydroxy, amino, alkylamino, carboxyl, alkoxycarbonyl, carboxamido, acylamino, amidino, sulfonamido, aminosulfonyl, alkylsulfonyl, aryl, heteroaryl, alkoxy, alkylthio; aryloxy og heteroaryloxy; Z er O, S, eller NH eller NR3; og W er en aryl- eller heteroaryl-radikal, som danner en fem-leddet eller seksleddet ring, som yderligere kan være kondenseret med fra 1 til 3 aryl-, heteroaryl-, cycloalkyl- eller heterocycloalkyl-ringe, hvilken W radikal kan være usubstitueret eller substitueret med op til fire substituenter valgt blandt halogen, hydroxyl, amino, carboxamido, carboxyl, cyano, sulfonamido, sulfonyl, alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, alkylthio, aryloxy og heteroaryloxy, og hvor vilkårlige to substituenter sammen kan danne en aromatisk eller ikke-aromatisk ringstruktur kondenseret med den nævnte aryl- eller heteroaryl-radikal W, hvilke substituenter fundet på W også eventuelt kan være bundet kovalent til enten Y eller R2, eller såvel Y som R2, for dannelse af heterocycliske eller carbocycliske ringsystemer, hvilke ringsystemer kan være aromatiske, heteroaromatiske eller delvis aromatiske.
3. T3SS inhibitor-forbindelsen ifølge krav 2, hvor W er valgt blandt
4. Forbindelse ifølge krav 1, valgt fra gruppen bestående af:
I uu
5. Forbindelse ifølge krav 1 eller 2, omfattende R-isomeren i ren form.
5 )
og specielle isomere af vilkårlige af de ovennævnte forbindelser.
6. Forbindelse ifølge krav 4, valgt blandt
7. Bakteriel type III sekretionssystem (T3SS) inhibitor-forbindelse med formlen I til anvendelse som et medikament:
formel I hvor A er uafhængigt CH eller N; X er uafhængigt valgt blandt hydrogen eller halogen; Z er O, S, NH; eller NR3, hvor R3 er alkyl; Ver NR2, O, eller CR3R4; R2, R3 og R4 er uafhængigt hydrogen eller alkyl; Y er valgt blandt: en divalent lige-kædet, forgrenet, eller cyclisk alkyl-, alkenyl- eller alkynyl-radikal med fra 1 til 6 carbonatomer, som kan indeholde ét eller flere heteroatomer, og som kan være usubstitueret eller substitueret med op til fire substituenter valgt blandt halogen, cyano, hydroxy, amino, alkylamino, carboxyl, alkoxycarbonyl, carboxamido, acylamino, amidino, sulfonamido, aminosulfonyl, alkylsulfonyl, aryl, heteroaryl, alkoxy, alkylthio, aryloxy og heteroaryloxy; oxygen; eller NR5, hvor R5 er hydrogen eller alkyl; W er en aryl- eller heteroaryl-radikal, som danner en fem-leddet eller seks-leddet ring, som yderligere kan være kondenseret med fra 1 til 3 aryl-, heteroaryl-, cycloalkyl- eller heterocycloalkyl-ringe, hvilken W-radikal kan være usubstitueret eller substitueret med op til 4 substituenter valgt blandt halogen, cyano, hydroxy, amino, alkylamino, carboxyl, alkoxycarbonyl, carboxamido, acylamino, amidino, sulfonamido, aminosulfonyl, alkylsulfonyl, aryl, heteroaryl, alkoxy, alkylthio, aryloxy og heteroaryloxy, og hvor vilkårlige to substituenter sammen kan danne en aromatisk eller ikke-aromatisk ringstruktur kondenseret med den nævnte aryl- eller heteroaryl-radikal W, hvilke substituenter fundet på W, også eventuelt kan være bundet kovalent til enten Y eller R2, eller såvel Y som R2, for dannelse af heterocycliske eller carbocycliske ringsystemer, hvilke ringsystemer kan være aromatiske heteroaromatiske eller delvis aromatiske.
8. Farmaceutisk sammensætning omfattende én eller flere bakterielle T3SS inhibitorforbindelser som angivet i et vilkårligt at kravene 2-7 og et farmaceutisk acceptabelt bærestof eller excipiens.
9. Farmaceutisk sammensætning ifølge krav 8, hvor den ene eller flere T3SS inhibitorforbindelse er R-isomeren i ren form.
10. Forbindelse som defineret i ethvert af kravene 2-7, til anvendelse ved behandling af infektion med gram-negative bakterier.
11. Forbindelse til anvendelse ifølge krav 10, hvor bakterieinfektionen er en infektion med Salmonella spp., Shigella flexneri, Pseudomonas spp., Yersinia spp., enteropathogenisk og enteroinvasive Escherichia coli og Chlamydia spp.
12. Forbindelse til anvendelse ifølge krav 10, hvor den bakterielle infektion er en infektion med Pseudomonas aeruginosa, Yersinia pestis eller Chlamydia trachomatis.
13. Forbindelse til anvendelse ifølge krav 10, omfattende indgivelse til et individ, som er inficeret med eller eksponeret for en gram-negativ bakterie, af en virksom mængde for at inhibere T3SS-medieret effektorsekretion.
14. Forbindelse til anvendelse ifølge krav 13, hvor individet er et menneske.
15. Forbindelse til anvendelse ifølge krav 10 eller 13, som yderligere omfatter indgivelse af en yderligere aktiv ingrediens valgt fra gruppen bestående af et antibiotikum, et antistof, et antiviralt middel, et anticancermiddel, et analgetikum, et immunostimu-lerende middel, et naturligt, syntetisk eller semisyntetisk hormon, et centralnervesystem stimulerende middel, et antiemetisk middel, et anti-histamin, et erythropoietin, et komplement-stimulerende middel, et sedativ, et muskel-afslappende middel, et anæstetikum, et antikonvulsivt middel, et anti-depressivt middel, et anti-psykotisk middel, og kombinationer deraf.
DK12812134.0T 2011-07-13 2012-07-13 Inhibitorer for det bakterielle type III sekretionssystem DK2731608T3 (da)

Applications Claiming Priority (2)

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US201161507259P 2011-07-13 2011-07-13
PCT/US2012/046676 WO2013010082A2 (en) 2011-07-13 2012-07-13 Inhibitors of bacterial type iii secretion system

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DK2731608T3 true DK2731608T3 (da) 2018-06-18

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US (1) US9340551B2 (da)
EP (1) EP2731608B1 (da)
JP (2) JP6105575B2 (da)
AU (1) AU2012281019B2 (da)
CA (1) CA2841487C (da)
DK (1) DK2731608T3 (da)
ES (1) ES2672719T3 (da)
PT (1) PT2731608T (da)
TR (1) TR201808305T4 (da)
WO (1) WO2013010082A2 (da)

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WO2013122041A1 (ja) * 2012-02-14 2013-08-22 日本曹達株式会社 アリールオキシ酢酸アミド化合物および有害生物防除剤
US10934244B2 (en) 2015-06-15 2021-03-02 Nmd Pharma A/S Compounds for use in treating neuromuscular disorders
WO2018204322A1 (en) * 2017-05-02 2018-11-08 Microbiotix, Inc. Multimeric inhibitors of bacterial type iii secretion system
US11730714B2 (en) 2017-12-14 2023-08-22 Nmd Pharma A/S Compounds for the treatment of neuromuscular disorders
US12440477B2 (en) 2017-12-14 2025-10-14 Nmd Pharma A/S Compounds for the treatment of neuromuscular disorders
US11147788B2 (en) 2017-12-14 2021-10-19 Nmd Pharma A/S Compounds for the treatment of neuromuscular disorders
US11591284B2 (en) 2017-12-14 2023-02-28 Nmd Pharma A/S Compounds for the treatment of neuromuscular disorders
US10385028B2 (en) 2017-12-14 2019-08-20 Nmd Pharma A/S Compounds for the treatment of neuromuscular disorders
EP4536638A2 (en) * 2022-06-06 2025-04-16 Microbiotix, Inc. Inhibitors of bacterial type iii secretion system

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JPS5867653A (ja) * 1981-10-20 1983-04-22 Ube Ind Ltd フエノキシアルカン酸のベンジルアミド誘導体および除草剤
US5037991A (en) * 1984-07-18 1991-08-06 Sandoz Ltd. Novel substituted aromatic compounds
CA2493313C (en) 2002-07-29 2010-03-09 F. Hoffmann-La Roche Ag Novel benzodioxoles
WO2005113514A2 (en) 2004-05-07 2005-12-01 Janssen Pharmaceutica, N.V. Substituted pyrimidines as inhibitors of bacterial type iii protein secretion systems
US20110130397A1 (en) 2006-09-22 2011-06-02 Soongyu Choi Pyrrolinone compounds as inhibitors of bacterial peptidyl trna hydrolase and uses thereof
EP2532239A3 (en) 2007-04-03 2013-03-13 E. I. du Pont de Nemours and Company Substituted benzene fungicides
EP2413696A4 (en) * 2009-04-03 2012-10-24 Sinai School Medicine COMPOSITIONS FOR THE TREATMENT OF ALZHEIMER'S DISEASE
JP5898061B2 (ja) * 2009-04-06 2016-04-06 マイクロバイオティックス， インク．Ｍｉｃｒｏｂｉｏｔｉｘ， Ｉｎｃ． 細菌のｉｉｉ型分泌系の阻害剤

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CA2841487A1 (en) 2013-01-17
US9340551B2 (en) 2016-05-17
US20140142134A1 (en) 2014-05-22
WO2013010082A2 (en) 2013-01-17
JP6105575B2 (ja) 2017-03-29
JP2014520859A (ja) 2014-08-25
EP2731608A4 (en) 2015-02-25
CA2841487C (en) 2017-01-24
TR201808305T4 (tr) 2018-07-23
AU2012281019B2 (en) 2016-05-12
EP2731608A2 (en) 2014-05-21
PT2731608T (pt) 2018-06-04
AU2012281019A1 (en) 2014-01-30
ES2672719T3 (es) 2018-06-15
WO2013010082A3 (en) 2014-05-08
EP2731608B1 (en) 2018-03-14
JP2016188212A (ja) 2016-11-04

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