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AR050186A1 - Derivados de amino-piperidina, su preparacion y su aplicacion en terapeutica. - Google Patents

Derivados de amino-piperidina, su preparacion y su aplicacion en terapeutica.

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Publication number
AR050186A1
AR050186A1 ARP050103111A ARP050103111A AR050186A1 AR 050186 A1 AR050186 A1 AR 050186A1 AR P050103111 A ARP050103111 A AR P050103111A AR P050103111 A ARP050103111 A AR P050103111A AR 050186 A1 AR050186 A1 AR 050186A1
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AR
Argentina
Prior art keywords
cycloalkyl
heterocycloalkyl
alkyl
aryl
group
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Application number
ARP050103111A
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English (en)
Inventor
Alain Braun
Bruno Cornet
Gilles Courtemanche
Olivier Crespin
Eykmar Fett
Cecile Pascal
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Sanofi Aventis
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Publication of AR050186A1 publication Critical patent/AR050186A1/es

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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
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—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 no 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/56—Nitrogen atoms
    • C07D211/58—Nitrogen atoms attached in position 4
    • 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
    • A61K31/439—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 the ring forming part of a bridged ring system, e.g. quinuclidine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
    • 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
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/32—Alcohol-abuse
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic 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
    • C07D401/02—Heterocyclic 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
    • C07D401/12—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic 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
    • C07D401/14—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic 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
    • C07D403/12—Heterocyclic 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 chain containing hetero atoms as chain links
    • 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
    • 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
    • C07D405/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Diabetes (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Addiction (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Psychiatry (AREA)
  • Child & Adolescent Psychology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Emergency Medicine (AREA)
  • Gynecology & Obstetrics (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Procedimiento de preparacion y aplicacion en terapéutica, en tratamiento y prevencion de obesidad, diabetes, disfuncion sexual, enfermedades cardiovasculares, antiinflamatorio, dependencia alcoholica. Reivindicacion 1: Compuesto que responde a la formula (1) en donde: Ra y Ra', idénticos o diferentes uno del otro, representan un átomo de H o un grupo alquilo o cicloalquilo; R1 representa un átomo de H o un grupo alquilo, cicloalquilo, heterocicloalquilo o arilo; R2 representa un grupo de formula -(CH2)x-(CO)y-Y o -(CO)y-(CH2)x-Y, en donde: x = 0, 1, 2, 3, o 4; y = 0 o 1; Y representa un átomo de H o un grupo hidroxilo, alquilo, cicloalquilo, alcoxi, arilo, heteroarilo o -NR11R12, siendo Y diferente de un átomo de H cuando x = y = 0, R11 y R12, idénticos o diferentes uno del otro, representan un átomo de H o un grupo alquilo, cicloalquilo, alcoxi o -NR13R14, o bien R11 y R12 forman juntos, con el átomo de N al cual están unidos, una estructura mono- o bicíclica que incluye de 4 a 10 anillos y que comprende eventualmente 1 a 3 heteroátomos suplementarios y/o 1 a 3 insaturaciones etilénicas o acetilénicas, estando este ciclo eventualmente sustituido en cualesquiera posiciones por 1 a 3 grupos seleccionados entre los átomos de halogeno y los grupos hidroxilos, alquilos, cicloalquilos y alcoxi; R13 y R14, idénticos o diferentes uno del otro, representan un átomo de H o un grupo alquilo, cicloalquilo o alcoxi o bien R13 y R14 forman juntos, con el átomo de N al cual están unidos, una estructura mono- o bicíclica tal como se definio más arriba; R3 representa 1 a 3 grupos, idénticos o diferentes unos de otros, situados en cualesquiera posiciones del nucleo al cual están unidos y seleccionados entre los átomos de halogeno y los grupos alquilos, cicloalquilos, -OR, -NRR', -CO-NRR', -NR-CO-R', -NR-CO-NRR', -NR-COOR', -NO2, -CN y -COOR; R5 representa un átomo de H o un grupo alquilo, R4 es seleccionado entre los grupos de formulas (a), (b) y (c), eventualmente sustituidos por un grupo oxo o mono o polisustituido por un grupo arilo o heteroarilo en donde: p = 0, 1, 2, o 3; m = 0, 1 o 2, y o bien a) X representa un anillo -N(R10)-, en donde: R10 es seleccionado entre: un grupo -(CH2)x-OR8, -(CH2)x-COOR8, - (CH2)x-NR8R9, -(CH2)x-CO-NR8R9 o -(CH2)x-NR8-COR9, -(CH2)x-COR8, en donde x = 1, 2, 3 o 4; un grupo cicloalquilo o heterocicloalquilo fusionado con un grupo arilo o heteroarilo; u grupo cicloalquilo, heterocicloalquilo, arilo, heteroarilo, alquilarilo, alquilheteroarilo, -CO-alquilo, -CO-cicloalquilo, -CO-heterocicloalquilo, -CO-arilo, -CO-heteroarilo, -CO-alquilarilo, -CO-alquilheteroarilo, -CS-alquilo, -CS-cicloalquilo, -CS-heterocicloalquilo, -CS-arilo, -CS-heteroarilo, -CS- alquilarilo, -CS-alquilheteroarilo, -CS-NR8R9, -C(=NH)-NR8R9, -SO2-alquilo, -SO2-cicloalquilo, -SO2-heterocicloalquilo, -SO2-arilo, -SO2-heteroarilo, -SO2-alquilarilo, -SO2-alquilheteroarilo o -SO2-NR8R9, estando los grupos alquilos, cicloalquilos, heterocicloalquilos, arilos o heteroarilos eventualmente sustituidos por 1 o más grupos seleccionados entre los grupos R, R', -OR, -NRR', -CO-NRR', -NR-CO-R', -NR-CO-NRR', -NO2, -CN y -COOR, OCOR, COR, OCONRR', NRCOOR' estando los grupos cicloalquilos o heterocicloalquilos eventualmente fusionados con un grupo arilo o heteroarilo, o bien R10 forma, con el átomo de N al cual está unido y un átomo de C situado en una posicion cualquiera de la estructura cíclica de la formula (a), pero no adyacente a dicho átomo de N, un puente que comprende de 3 a 5 anillos; R8 y R9 son seleccionados independientemente uno del otro entre un átomo de H y los grupos alquilos, cicloalquilos, heterocicloalquilos, arilos, heteroarilos, alquilarilos, alquilheteroarilos, -CO-alquilos, -CO-cicloalquilos, -CO-heterocicloalquilos, -CO-arilos, -CO-heteroarilos, -CO-alquilarilos, -CO-alquilheteroarilos, -SO2-alquilos, -SO2-cicloalquilos, -SO2-heterocicloalquilos, -SO2-arilos, -SO2-heteroarilos, -SO2- alquilarilos, -SO2-alquilheteroarilos, -C(=NH)-NRR', COOR, -CONRR', -CSNRR' y -(CH2)x-OR, o x = 0, 1, 2, 3 o 4, o bien R8 y R9 forman juntos un cicloalquilo o un heterocicloalquilo, R y R' representan independientemente uno del otro un átomo de H o un grupo alquilo, cicloalquilo, heterocicloalquilo, arilo, heteroarilo, alquilarilo o alquilheteroarilo, o pueden formar juntos un cicloalquilo o un heterocicloalquilo, o bien, b) X representa un anillo -C(R6)(R7)-, en donde R6 es seleccionado entre: un átomo de H, un átomo e halogeno, un grupo -(CH2)x-OR8, -(CH2)x-COOR8, -(CH2)x-NR8R9, -(CH2)x-CO-NR8R9 o -(CH2)x-NR8-COR9, en donde x = 0, 1, 2, 3 o 4, un grupo alquilo, cicloalquilo, heterocicloalquilo, arilo, heteroarilo, alquilarilo, alquilheteroarilo, -CO-alquilo, -CO-cicloalquilo, -CO-heterocicloalquilo, -CO-arilo, -CO-heteroarilo, -CO-alquilarilo o -CO-alquilheteroarilo, -CS-alquilo, -CS-cicloalquilo, -CS-heterocicloalquilo, -CS-arilo, -CS-heteroarilo, -CS-alquilarilo, -CS- alquilheteroarilo, -CS-NR8R9, -C(=NH)-NR8R9, un grupo cicloalquilo o heterocicloalquilo fusionado o no situado en posicion spiro sobre el ciclo de formula (a) al cual está unido; un grupo cicloalquilo o heterocicloalquilo fusionado con un grupo arilo o heteroarilo, estando los grupos alquilos, cicloalquilos, heterocicloalquilos, arilos, o heteroarilos eventualmente sustituidos por 1 o más grupos seleccionados entre los grupos R, R', -OR, -NRR', -CO-NRR', -NR-CO-R', -NR-CO-NRR', -NO2, -CN y -COOR, OCOR, COR, OCONRR', NRCOOR',estando los grupos cicloalquilos o heterocicloalquilos eventualmente fusionados con un grupo arilo o heteroarilo; R7 es seleccionado entre los átomos de H y de halogeno y los grupos alquilos, cicloalquilos, arilos, heteroarilos, alquilarilos, alquilheteroarilos, -OR, -O-arilos, -O-heteroarilos, -O-alquilarilos, -O-alquilheteroarilos,-NRR', CO-NRR', -NR-CO-R'; -NR-CO-NRR', NRCOOR', NO2, -CN y -COOR, R8 y R9 son seleccionados independientemente uno del otro entre un átomo de H y los grupos alquilos, cicloalquilos, heterocicloalquilos, arilos, heteroarilos, alquilarilos, alquilheteroarilos, -CO-alquilos, -CO-cicloalquilos, -CO-heterocicloalquilos, -CO-arilos, -CO-heteroarilos, -CO-alquilarilos, -CO- alquilheteroarilos, -SO2-alquilos, -SO2-cicloalquilos, -SO2-heterocicloalquilos, -SO2-arilos, -SO2-heteroarilos, -SO2-alquilarilos, -SO2-alquilheteroarilo, -C(=NH)-NRR', COOR, -CO-NRR', -CS-NRR', y -(CH2)x-OR, en donde x = 0, 1, 2, 3 o 4, estando los grupos alquilos y arilos eventualmente sustituidos por 1 o mas grupos seleccionados entre los grupos R, R', -OR, -NRR', -CO-NRR', -NR-CO-R', -NR-CO-NRR', -NO2, -CN y -COOR, OCOR, COR, OCONRR', NRCOOR', o bien R8 y R9 forman juntos un cicloalquilo o un heterocicloalquilo; R y R' representan independientemente uno del ,otro un átomo de H o un grupo alquilo, cicloalquilo, heterocicloalquilo, arilo, heteroarilo, alquilarilo o alquilheteroarilo, o pueden formar juntos un cicloalquilo o un heterocicloalquilo, en el estado de base o de sal de adicion de un ácido, así como en el estado de hidrato o de solvato.
ARP050103111A 2004-07-29 2005-07-27 Derivados de amino-piperidina, su preparacion y su aplicacion en terapeutica. AR050186A1 (es)

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FR0408370A FR2873691B1 (fr) 2004-07-29 2004-07-29 Derives d'amino-piperidine, leur preparation et leur application en therapeutique

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US (1) US20070191364A1 (es)
EP (1) EP1786809A2 (es)
JP (1) JP2008508241A (es)
KR (1) KR20070047804A (es)
CN (1) CN101039941A (es)
AR (1) AR050186A1 (es)
AU (1) AU2005276354A1 (es)
BR (1) BRPI0512688A (es)
CA (1) CA2574454A1 (es)
FR (1) FR2873691B1 (es)
IL (1) IL180766A (es)
MX (1) MX2007001137A (es)
PE (1) PE20060562A1 (es)
RU (1) RU2376303C2 (es)
TW (1) TW200621768A (es)
UY (1) UY29041A1 (es)
WO (1) WO2006021656A2 (es)

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CN101039941A (zh) 2007-09-19
MX2007001137A (es) 2007-04-19
FR2873691B1 (fr) 2006-10-06
UY29041A1 (es) 2006-02-24
WO2006021656A3 (fr) 2006-06-08
CA2574454A1 (fr) 2006-03-02
JP2008508241A (ja) 2008-03-21
KR20070047804A (ko) 2007-05-07
AU2005276354A1 (en) 2006-03-02
EP1786809A2 (fr) 2007-05-23
IL180766A0 (en) 2007-06-03
RU2376303C2 (ru) 2009-12-20
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WO2006021656A2 (fr) 2006-03-02
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