DK1868998T3 - Nye heterocykliske forbindelser, fremstilling deraf og anvendelse deraf som medikamenter, især som anti-alzheimer-midler - Google Patents

Nye heterocykliske forbindelser, fremstilling deraf og anvendelse deraf som medikamenter, især som anti-alzheimer-midler Download PDF

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DK1868998T3
DK1868998T3 DK06742673.4T DK06742673T DK1868998T3 DK 1868998 T3 DK1868998 T3 DK 1868998T3 DK 06742673 T DK06742673 T DK 06742673T DK 1868998 T3 DK1868998 T3 DK 1868998T3
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methyl
dimethylcarbamate
stage
dihydroquinoline
carboxylate
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DK06742673.4T
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Pierre Bohn
Vincent Levacher
Fur Nicolas Le
Francis Marsais
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Vfp Therapies
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
    • C07D211/96—Sulfur atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
    • C07D211/86—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
    • C07D211/90—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
    • 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
    • C07D215/24—Oxygen atoms attached in position 8
    • C07D215/26—Alcohols; Ethers thereof
    • C07D215/32—Esters
    • C07D215/34—Carbamates
    • 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
    • C07D215/36—Sulfur 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
    • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
    • C07D217/24—Oxygen atoms
    • 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
    • C07D413/04—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 directly linked by a ring-member-to-ring-member bond

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Neurosurgery (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Psychiatry (AREA)
  • Hospice & Palliative Care (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Claims (12)

1. Ethyl 1 -methyl-7-(A/,A/-dimethylcarbamat)-1,4-dihydroquinolin-3-carboxylat;
1. Ethyl 1 -methyl-7-(A/,A/-dimethylcarbamat)-1,4-dihydroquinolin-3-carboxylat;
1. Forbindelse med formel G3a eller G3+
hvor Ri er (C1-C4) alkyl, R2 er H, (C1-C4) alkyl, R3 er en elektrontrækkende gruppe udvalgt fra gruppen omfattende COOR, COSR, CONRR', CN, COR, CF3, SOR, S02R, SONRR', S02NRR', N02, halogen, heteroaryl, hvor R, R' er en gruppe H, alkyl, cycloalkyl, arylalkyl, heteroarylalkyl, hydroxyalkyl, alkoxyalkyl, aryloxyalkyl, alkylaminoalkyl, aminoalkyl, heteroaryloxyalkyl, ha-logenoalkyl, thioalkyl, thioalkoxyalkyl, aryl, alkylaryl, hydroxyaryl, alkoxyaryl, aryloxyaryl, aminoaryl, alkylaminoaryl, halogenoaryl, heteroaryl, alkylheteroa-ryl, alkoxyheteroaryl, aminoheteroaryl, alkylaminoheteroaryl, halogenohe-teroaryl, eller R og R' sammen med det nitrogenatom, hvortil de er knyttet, danner en hete-rocyklisk ring med mindst 3 led, fortrinsvis en 5- eller 6-leddet heterocyklisk ring, eventuelt substitueret med en eller flere grupper, der er som defineret for R2, eller R og R' sammen med det nitrogenatom, hvortil de er knyttet, danner et kondenseret polyheterocyklisk system fortrinsvis tetrahydroisoquinolin, indolin, isoindolin, eventuelt substitueret med en eller flere grupper, der er som defineret for R2, R4 og R6 er Η, Zi er OCONR7R8, R7 og Rs, som er identiske eller forskellige, er hydrogen, (C1-C8) alkyl, aryl, heteroaryl, (C1-C8) alkylaryl, phenyl, cyclop-ropyl, (CH2)n-COOH; og hvor n ligger mellem 1 og 6; eller et farmaceutisk salt eller en stereoisomer deraf.
2. Ethyl 1 -methyl-5-(/V,/V-dimethylcarbamat)-1,4-dihydroquinolin-3-carboxylat;
67. Methyl 1 -methyl-5-(N,N-dimethylcarbamat)-1,4-dihydroquinolin-3-carboxylat; 68. 1 -Methyl-3-(N-methylcarboxamido)-5-(N,N-dimethylcarbamat)-1,4-dihydroquinolin; 69. [3-(N,N-methylcarboxamido)-5-(N,N-dimethylcarbamat)]-1,4-dihydroquinolin; 74. [Methyl 1-methyl-8-(N,N-dimethylcarbamat)-3-carboxylat]-1,4- dihydroquinolin eller 1,2-dihydroquinolin;
76. Methyl 1 -methyl-5-(N-ethylcarbamat)-1,4-dihydroquinolin-3-carboxylat; 77. [Ethyl 1-methyl-8-(N,N-dimethylcarbamat)-3-carboxylat]-1,4- dihydroquinolin; 78. 1 -Methyl-3-(N-propylcarboxamido)-7-(N,N-dimethylcarbamat)-1,4- dihydroquinolin eller deres tilsvarende ammoniumform deraf.
2. Ethyl 1 -methyl-5-(A/,A/-dimethylcarbamat)-1,4-dihydroquinolin-3-carboxylat;
2. Forbindelse med formel G3 eller G3+ som defineret i krav 1:
3. Forbindelse med formel G3 eller G3+ ifølge krav 2:
3. Ethyl 1 -methyl-5,7-di(A/,A/-dimethylcarbamat)-1,4-dihydroquinolin-3- carboxylat;
4. Forbindelse med formel G3 eller G3+ ifølge krav 2 eller 3:
67. Methyl 1 -methyl-5-(N,N-dimethylcarbamat)-1,4-dihydroquinolin-3-carboxylat; 68. 1 -Methyl-3-(N-methylcarboxamido)-5-(N,N-dimethylcarbamat)-1,4-dihydroquinolin eller deres tilsvarende ammoniumform deraf.
4. Ethyl 1 -methyl-5,8-di(A/,A/-dimethylcarbamat)-1,4-dihyd roquinolin-3- carboxylat;
5. Inklusionskompleks af en forbindelse som defineret i et hvilket som helst af kravene 1 til 4 med en beta-cyclodextrin.
5. Ethyl 1 -methyl-5-(N,N-dimethylthiocarbamat)-1,4-dihydro-5-0-quinolin-3-carboxylat;
6. Inklusionskompleks ifølge krav 5 med en hydroxypropyl-betacyclodextrin.
6. Ethyl 1 -methyl-5-(A/,A/-dimethylthiocarbamat)-1,4-dihydro-5-S-quinolin-3-carboxylat; 7. 1 -Methyl-5-(A/,A/-dimethylcarbamat)-3-(A/,A/-diethylcarboxamido)-1,4-dihydroquinolin; 8. 1-Methyl-7-(A/,A/-dimethylcarbamat)-3-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)-1,4-dihydroquinolin; 9. 1 -Methyl-5-(A/,A/-dimethylcarbamat)-3-trifluoromethyl-1,4-dihydroquinolin; 10. (+/-)-1 -Methyl-3-(4-methylphenylsulfinyl)-5-(A/,A/-dimethylcarbamat)-1,4-quinolin; 11. 1 -Methyl-3-(4-methylphenylsulfonyl)-5-(A/,A/-dimethylcarbamat)-1,4-dihydroquinolin; 12. 1 -Methyl-5-(A/,A/-dimethylcarbamat)-3-(A/-phenylsulfomanid)-1,4-dihydroquinolin; 13. 1 -Methyl-6,7-di(A/,A/-dimethylcarbamat)-3-nitro-1,4-dihydroquinolin;
14. Ethyl 1-methyl-2-phenyl-6,7-di(A/,A/-dimethylcarbamat)-1,4- dihydroquinolin-3-carboxylat;
15. Ethyl 1,2,4-trimethyl-7-(A/,A/-dimethylcarbamat)-1,4-dihydroquinolin-3-carboxylat; 16. ; 17. - 18. - 19. - 20. -21. -22. - 23. - 24. - 25. - 26. -27. - 28. - 29. - 30. - 31. - 32. - 33. - 34. - 35. - 36. - 37. - 38. - 39. - 40. - 41. - 42. - 43. - 44. - 45. - 46. - 47. - 48. - 49. -59. - 51. - 52. - 53. - 54. - 55. - 56. - 57. - 58. - 59. - 69. -61. -62. -63. - 64. - 65. - 66. -
67. Methyl 1-methyl-5-(A/,A/-dimethylcarbamat)-1,4-dihydroquinolin-3-carboxylat; 68. 1 -Methyl-3-(N-methylcarboxamido)-5-(/V,/V-dimethylcarbamat)-1,4-dihydroquinolin; 69. [3-(N,N-methylcarboxamido)-5-(N,N-dimethylcarbamat)]-1,4-dihydroquinolin; 70. 71. - 72. - 73. - 74. [Methyl 1-methyl-8-(N,N-dimethylcarbamat)-3-carboxylat]-1,4- dihydroquinolin; 75. ;
76. Methyl 1 -methyl-5-(N-ethylcarbamat)-1,4-dihydroquinolin-3-carboxylat; 77. [Ethyl 1-methyl-8-(A/,A/-dimethylcarbamat)-3-carboxylat]-1,4- dihydroquinolin; 78. 1 -Methyl-3-(N-propylcarboxamido)-7-(N,N-dimethylcarbamat)-1,4-dihydroquinolin; eller deres tilsvarende ammoniumform deraf.
7. Farmaceutisk sammensætning omfattende mindst en forbindelse ifølge et hvilket som helst af kravene 1 til 6 og en farmakologisk acceptabel bærer.
8. Farmaceutisk sammensætning ifølge krav 7 til anvendelse ved behandling af neurodegenerative sygdomme, fortrinsvis Alzheimers sygdom hos et humant eller andet dyreindivid.
9. Forbindelse med formel G'3;
G’3 hvor R2 R3 R4 R6, Z-i er som defineret i krav 1.
10. Fremgangsmåde til fremstilling af en forbindelse med formel G3a, ifølge krav 1, som omfatter trinnet med reduktion af en forbindelse med formel (G3+) W\ hvor W er en fraspaltelig enhed udvalgt blandt halogen, O-triflat, carbo-xylat, sulfat, tosylat, mesylat, i nærvær af et reduktionsmiddel.
11. Fremgangsmåde til fremstilling af en forbindelse med formel (G3+)W som defineret i krav 1, som omfatter et trin med kvaternisering af nitrogenatomet af en forbindelse med formed G'3 som defineret i krav 9, ved hjælp af et alky- leringsmiddel RrW, idet Ri er (C1-C4) alkyl; idet W er en fraspaltelig enhed som defineret i krav 10.
12. Fremgangsmåde til fremstilling af en forbindelse med formel G'3 ifølge krav 9, som omfatter et trin med carbamylering af en forbindelse med følgende formel E3
E3 hvor P er OH; med et middel med formel W- CO-NR7R8 hvor W er en fraspaltelig enhed udvalgt blandt halogen, O-triflat, sulfat, to-sylat, mesylat, og R2 R3 R4, R7, Rs har den samme betydning som defineret i krav 1.
DK06742673.4T 2005-04-01 2006-03-29 Nye heterocykliske forbindelser, fremstilling deraf og anvendelse deraf som medikamenter, især som anti-alzheimer-midler DK1868998T3 (da)

Applications Claiming Priority (3)

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EP05290719 2005-04-01
EP05290914A EP1731507A1 (en) 2005-04-26 2005-04-26 New heterocyclic compounds, their preparation and their use as medicaments, in particular as anti-alzheimer agents
PCT/EP2006/003787 WO2006103120A2 (en) 2005-04-01 2006-03-29 New heterocyclic compounds, their preparation and their use as medicaments, in particular as anti-alzheimer agents

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US (1) US7977354B2 (da)
EP (1) EP1868998B1 (da)
AU (1) AU2006228683B2 (da)
CA (1) CA2603345C (da)
DK (1) DK1868998T3 (da)
IL (1) IL186233A (da)
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AR072899A1 (es) 2008-08-07 2010-09-29 Merck Sharp & Dohme Derivados de terpiridina-carboxamida antagonistas de receptores de orexina, composiciones farmaceuticas que los contienen y uso de los mismos en el tratamiento del insomnio y la obesidad.
EP2350010B1 (en) * 2008-10-30 2014-03-26 Merck Sharp & Dohme Corp. Isonicotinamide orexin receptor antagonists
WO2012087872A1 (en) 2010-12-23 2012-06-28 Merck Sharp & Dohme Corp. Quinolines and aza-quinolines as crth2 receptor modulators
MX2013007295A (es) 2010-12-23 2013-08-26 Merck Sharp & Dohme Quinoxalinas y aza-quinoxalinas como moduladores del receptor de crth2.
US8946261B2 (en) 2011-02-14 2015-02-03 Council Of Scientific & Industrial Research Substituted 1, 2, 3, 4-tetrahydroquinolin-7-yl carbamates as acetylcholinesterase inhibitors for treatment of Alzheimer's disease
WO2014113495A1 (en) * 2013-01-15 2014-07-24 The Trustees Of Columbia University In The City Of New York Activation or reactivation of ache
EP2759536A1 (en) 2013-01-25 2014-07-30 INSA (Institut National des Sciences Appliquees) de Rouen Oxidisable pyridine derivatives, their preparation and use as anti-Alzheimer agents
JP6669499B2 (ja) 2013-02-15 2020-03-18 カラ ファーマシューティカルズ インコーポレイテッド 治療用化合物
US9688688B2 (en) 2013-02-20 2017-06-27 Kala Pharmaceuticals, Inc. Crystalline forms of 4-((4-((4-fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxyquinazolin-7-yl)oxy)-1-(2-oxa-7-azaspiro[3.5]nonan-7-yl)butan-1-one and uses thereof
US9353123B2 (en) 2013-02-20 2016-05-31 Kala Pharmaceuticals, Inc. Therapeutic compounds and uses thereof
US9890173B2 (en) 2013-11-01 2018-02-13 Kala Pharmaceuticals, Inc. Crystalline forms of therapeutic compounds and uses thereof
CN106061261B (zh) 2013-11-01 2018-04-24 卡拉制药公司 治疗化合物的结晶形式及其用途
CN105622501B (zh) * 2016-03-30 2019-02-19 皖南医学院 N-芳基-3-碘代喹啉衍生物及其制备方法
AU2017324716B2 (en) 2016-09-08 2020-08-13 KALA BIO, Inc. Crystalline forms of therapeutic compounds and uses thereof
US10253036B2 (en) 2016-09-08 2019-04-09 Kala Pharmaceuticals, Inc. Crystalline forms of therapeutic compounds and uses thereof
EP3509421A4 (en) 2016-09-08 2020-05-20 Kala Pharmaceuticals, Inc. CRYSTALLINE FORMS OF THERAPEUTIC COMPOUNDS AND USES THEREOF
UA126119C2 (uk) * 2016-11-11 2022-08-17 Баєр Енімал Хелс Гмбх Протигельмінтні похідні хінолін-3-карбоксаміду
KR20220087497A (ko) 2019-10-18 2022-06-24 더 리전츠 오브 더 유니버시티 오브 캘리포니아 병원성 혈관을 표적화하기 위한 화합물 및 방법

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WO2006103120A2 (en) 2006-10-05
US20090062279A1 (en) 2009-03-05
SG161217A1 (en) 2010-05-27
IL186233A (en) 2012-07-31
EP1868998A2 (en) 2007-12-26
WO2006103120A3 (en) 2007-02-15
AU2006228683B2 (en) 2012-02-02
AU2006228683A1 (en) 2006-10-05
CA2603345C (en) 2017-05-02
NZ561953A (en) 2011-11-25
US7977354B2 (en) 2011-07-12
IL186233A0 (en) 2008-01-20
CA2603345A1 (en) 2006-10-05

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