AR061444A1 - Compuestos terapeuticos derivados de bencimidazol y un metodo para prepararlos - Google Patents

Compuestos terapeuticos derivados de bencimidazol y un metodo para prepararlos

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Publication number
AR061444A1
AR061444A1 ARP070102564A ARP070102564A AR061444A1 AR 061444 A1 AR061444 A1 AR 061444A1 AR P070102564 A ARP070102564 A AR P070102564A AR P070102564 A ARP070102564 A AR P070102564A AR 061444 A1 AR061444 A1 AR 061444A1
Authority
AR
Argentina
Prior art keywords
alkyl
cycloalkyl
heterocyclyl
heterocycloalkyl
cycloalkenyl
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Application number
ARP070102564A
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English (en)
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Astrazeneca Ab
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=38831987&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=AR061444(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab
Publication of AR061444A1 publication Critical patent/AR061444A1/es

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    • 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
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/10—Laxatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/12—Antidiarrhoeals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/14—Antitussive agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P23/00—Anaesthetics
    • 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
    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • A61P25/06—Antimigraine agents
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • A61P25/22—Anxiolytics
    • 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
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
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    • 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
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    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/32—Alcohol-abuse
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    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/34—Tobacco-abuse
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    • 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
    • A61P25/36—Opioid-abuse
    • 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
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic 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
    • 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
    • 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
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/08—Radicals containing only hydrogen and carbon atoms
    • 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
    • C07D401/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D403/06—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 carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic 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
    • C07D417/14—Heterocyclic 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 three or more hetero rings

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Immunology (AREA)
  • Addiction (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Psychology (AREA)
  • Pulmonology (AREA)
  • Oncology (AREA)
  • Transplantation (AREA)
  • Hospice & Palliative Care (AREA)
  • Communicable Diseases (AREA)
  • Virology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Rheumatology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Anesthesiology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

Reivindicacion 1: Un compuesto de la formula (1), una sal aceptable para uso farmacéutico del mismo, un diastereomero, un enantiomero o una mezcla de los mismo donde R1 está seleccionado entre alquilo C1-10, alquenilo C-1-10, alcoxi C1-10, aril C6- 10-alquilo C1-6 aril C6-10-C(=O)-alquilo C1-6, cicloalquil C3-10alquilo C1-6, cicloalquenil C4-8-alquilo C1-6, heterociclil C3-6-alquilo C1-6, heterociclil C3-8-C(O)-alquilo C1-6, arilo C6-10, aril C6-10-C(=O)-, cicloalquilo C3-10, cicloalquenilo C4- 8, heterociclilo C3-6 y heterociclil C3-6-C()-; donde dicho alquilo C1-10 alquenilo C2-10, alcoxi C1-10, aril C6-10-alquilo C1-6, aril6-10-C(=O)-alquilo C-6, cicloalquil C3-10-alquilo C1-6, cicloalquenil C4-8-alquilo C1-6, heterociclil C3-6-alquilo C1-6, heterociclil C3-6-C(=O)-alquilo C1-6, arilo C6-10, aril C6-10-C(O)-, cicloalquilo C3-10, cicloalquenilo C4-8, heterociclilo C3-6 o heterociclil C3-6-C(=O)- está optativamente sustituido con uno o más grupos seleccionados entre carboxi, -(C=O)- NH2, halogeno, ciano, nitro metoxi, etoxi, metilo, etilo, hidroxi, -N(R6)-C(O)R5 , -S(=O)2-NR5R6, -C(=O)-NR5R6, -NH-C(=O)-NR5R6 y -NR5R6; R2 está seleccionado del grupo formado por alquilo C1-10, alquenilo C2-10, alquinilo C2-10, cicloalquilo C3-8, cicloalquil C3-8-alquilo C1-6 cicloalquenilo C4-8-alquilo C1-6, heterocicloalquil C3-6-alquilo C1-6, cicloalquenilo C4-8 y heterocicloalquilo C3-6, donde dicho alquilo C1-10, alquenilo C2-10, alquinilo C2-10 cicloalquilo C3-8 cicloalquil C3-8- alquilo C1-6, cicloalquenil C4-8-alquilo C1-6, heterocicloalquil C3-6-alquilo C1-6, cicloalquenilo C4-8 o heterocicloalquilo C3-6utilizado en la definicion de R2 está optativamente sustituido con uno o más grupos seleccionados entre carboxi, -(=O)- NH2, halogeno, ciano, nitro, metoxi etoxi, metilo, etilo, hidroxi y -NR5 y R6; R3 está seleccionado entre alquilo C1-6, alquenilo C2-6, cicloalquilo C3-6, cicloalquil C3-6-alquilo C1-4, heteroarilo C2-5, heteroaril C2-5-alquilo C1-4, heterocicloalquilo C2-5, heterocicloalquil C2-5-alquilo C1-4, fenilo y bencilo, donde dicho alquilo C1-6, alquenilo C2-6, cicloalquilo C3-6, cicloalquil C3-6-alquilo C1-4, heteroarilo C2-5, heteroaril C2-5-alquilo C1-4, heterocicloalquilo C2-5, heterocicloalquil C2-5-alquilo C1-4, fenilo o bencilo está optativamente sustituido con uno o más grupos seleccionados entre alquilo C1-6, carboxi, halogeno, ciano, nitro, metoxi, etoxi, hidroxi, y NR5R6; y R4 está seleccionado entre alquilo 1-6, carboxi, halogeno, ciano, nitro, metoxi, etoxi, hidroxi y -NR5R6; el anillo a es un heterociclo de 4,5,o 6 miembros que optativamente contiene uno o dos heteroátomos más seleccionados entre O, S y N en su anillo, además del nitrogeno ilustrado; X está seleccionado entre -O-C(=O)-, -C(=O)-NH-, -NH-C(=O)-, -NHR7-C(=O)-, -C(=O)NHCH2-, -NH-C(=O)CH2, -NH-C(=O)-NH, -O-C(=O)-NH-, NH-(CH2)m-, -C(O)-O- y -NH-C(=O)-O-; donde R5 y R6 están independientemente seleccionados entre -H, alquilo C1-6 optativamente sustituido con -OH, metoxi, etoxi o halogeno, cicloalquil C3-6-alquilo C0-m optativamente sustituido con -OH, metoxi, etoxi o halogeno, alquenilo C2-6 optativamente sustituido con -OH, metoxi, etoxi o halogeno, y un alquileno C1-6 bivalente optativamente sustituido con -OH, metoxi, etoxi o halogeno que, junto con otro R5 y R6 bivalente, forma una porcion de un anillo; R7 es alquilo C1-6 y m es , 1, 2, o 3.
ARP070102564A 2006-06-13 2007-06-12 Compuestos terapeuticos derivados de bencimidazol y un metodo para prepararlos AR061444A1 (es)

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US (1) US20100305140A1 (es)
EP (1) EP2035409A4 (es)
JP (1) JP2009539972A (es)
KR (1) KR20090021216A (es)
CN (1) CN101501022A (es)
AR (1) AR061444A1 (es)
AU (1) AU2007259425B2 (es)
BR (1) BRPI0712305A2 (es)
CA (1) CA2654250A1 (es)
CL (1) CL2007001715A1 (es)
EC (1) ECSP088968A (es)
IL (1) IL195426A0 (es)
MX (1) MX2008015157A (es)
NO (1) NO20090125L (es)
RU (1) RU2008148905A (es)
TW (1) TW200808772A (es)
UY (1) UY30412A1 (es)
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SE0302573D0 (sv) * 2003-09-26 2003-09-26 Astrazeneca Ab Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof
US20110086853A1 (en) * 2009-10-08 2011-04-14 William Brown Therapeutic Compounds
US20230391752A1 (en) * 2020-10-22 2023-12-07 Chulalongkorn University Pyrrolidine-3-carboxamide derivatives and related uses

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JP3295277B2 (ja) * 1994-06-01 2002-06-24 呉羽化学工業株式会社 抗腎疾患剤及びベンズイミダゾール誘導体
US6348032B1 (en) * 1998-11-23 2002-02-19 Cell Pathways, Inc. Method of inhibiting neoplastic cells with benzimidazole derivatives
PA8535601A1 (es) * 2000-12-21 2002-11-28 Pfizer Derivados benzimidazol y piridilimidazol como ligandos para gabaa
SE0101387D0 (sv) * 2001-04-20 2001-04-20 Astrazeneca Ab Novel compounds
SE0301699D0 (sv) * 2003-06-10 2003-06-10 Astrazeneca Ab Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof
SE0301698D0 (sv) * 2003-06-10 2003-06-10 Astrazeneca Ab Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof
EP1797078A4 (en) * 2004-09-24 2009-04-01 Astrazeneca Ab BENZIMIDAZOLE DERIVATIVES, COMPOSITIONS CONTAINING THESE DERIVATIVES, PREPARATION AND USES THEREOF

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EP2035409A4 (en) 2012-01-04
AU2007259425B2 (en) 2011-09-08
NO20090125L (no) 2009-03-09
CA2654250A1 (en) 2007-12-21
IL195426A0 (en) 2009-08-03
US20100305140A1 (en) 2010-12-02
JP2009539972A (ja) 2009-11-19
CN101501022A (zh) 2009-08-05
KR20090021216A (ko) 2009-02-27
WO2007145563A1 (en) 2007-12-21
TW200808772A (en) 2008-02-16
MX2008015157A (es) 2008-12-12
AU2007259425A1 (en) 2007-12-21
AU2007259425A8 (en) 2009-01-29
WO2007145563A8 (en) 2008-11-13
RU2008148905A (ru) 2010-07-20
EP2035409A1 (en) 2009-03-18
UY30412A1 (es) 2008-01-31
BRPI0712305A2 (pt) 2012-01-17
ZA200809977B (en) 2010-04-28
CL2007001715A1 (es) 2008-01-18

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