ATE419250T1 - 2-cyanopyrrolidincarbonsäureamide als dipeptidylpeptidase-iv-inhibitoren - Google Patents

2-cyanopyrrolidincarbonsäureamide als dipeptidylpeptidase-iv-inhibitoren

Info

Publication number
ATE419250T1
ATE419250T1 AT04793389T AT04793389T ATE419250T1 AT E419250 T1 ATE419250 T1 AT E419250T1 AT 04793389 T AT04793389 T AT 04793389T AT 04793389 T AT04793389 T AT 04793389T AT E419250 T1 ATE419250 T1 AT E419250T1
Authority
AT
Austria
Prior art keywords
cyanopyrrolidinecarbonic
dipeptidylpeptidase
inhibitors
acid amides
amides
Prior art date
Application number
AT04793389T
Other languages
German (de)
English (en)
Inventor
Ichiro Shima
Akio Kuroda
Takehiko Ohkawa
Toshio Kurosaki
Yuki Sawada
Aiko Wada
Original Assignee
Astellas Pharma Inc
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
Priority claimed from AU2003906010A external-priority patent/AU2003906010A0/en
Application filed by Astellas Pharma Inc filed Critical Astellas Pharma Inc
Application granted granted Critical
Publication of ATE419250T1 publication Critical patent/ATE419250T1/de

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D453/00Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
    • 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
    • C07D401/06Heterocyclic 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
    • 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
    • A61K31/40Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/4025Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil not condensed and containing further heterocyclic rings, e.g. cromakalim
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00Drugs for disorders of the urinary system
    • A61P13/12Drugs for disorders of the urinary system of the kidneys
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/02Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/02Drugs for disorders of the nervous system for peripheral neuropathies
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/06Antihyperlipidemics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/08Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • A61P31/14Antivirals for RNA viruses
    • A61P31/18Antivirals for RNA viruses for HIV
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • A61P37/04Immunostimulants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • A61P37/06Immunosuppressants, e.g. drugs for graft rejection
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00Drugs for disorders of the endocrine system
    • A61P5/10Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/12Antihypertensives
    • 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
    • C07D401/14Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic 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
    • C07D403/06Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D451/00Heterocyclic 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
    • C07D451/02Heterocyclic 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
    • C07D451/04Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/08Bridged systems

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Diabetes (AREA)
  • Endocrinology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Urology & Nephrology (AREA)
  • Virology (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Emergency Medicine (AREA)
  • Gastroenterology & Hepatology (AREA)
  • AIDS & HIV (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Molecular Biology (AREA)
  • Vascular Medicine (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Transplantation (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Rheumatology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Epidemiology (AREA)
AT04793389T 2003-10-31 2004-10-29 2-cyanopyrrolidincarbonsäureamide als dipeptidylpeptidase-iv-inhibitoren ATE419250T1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AU2003906010A AU2003906010A0 (en) 2003-10-31 DPP-IV Inhibitor
AU2004900961A AU2004900961A0 (en) 2004-02-25 DPP-IV inhibitor

Publications (1)

Publication Number Publication Date
ATE419250T1 true ATE419250T1 (de) 2009-01-15

Family

ID=34553068

Family Applications (1)

Application Number Title Priority Date Filing Date
AT04793389T ATE419250T1 (de) 2003-10-31 2004-10-29 2-cyanopyrrolidincarbonsäureamide als dipeptidylpeptidase-iv-inhibitoren

Country Status (17)

Country Link
US (1) US7186731B2 (enExample)
EP (1) EP1737863B1 (enExample)
JP (1) JP4636021B2 (enExample)
KR (1) KR20060100390A (enExample)
AR (1) AR046313A1 (enExample)
AT (1) ATE419250T1 (enExample)
BR (1) BRPI0415587A (enExample)
CA (1) CA2543533A1 (enExample)
CO (1) CO5690603A2 (enExample)
DE (1) DE602004018837D1 (enExample)
ES (1) ES2320557T3 (enExample)
IL (1) IL175214A0 (enExample)
MX (1) MXPA06004797A (enExample)
NO (1) NO20062517L (enExample)
RU (1) RU2006118789A (enExample)
TW (1) TW200528440A (enExample)
WO (1) WO2005042533A2 (enExample)

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ES2327857T3 (es) 2004-05-12 2009-11-04 Pfizer Products Inc. Derivados de prolina y su uso como inhibidores de la dipeptidil peptidasa iv.
CN101193852A (zh) * 2005-02-18 2008-06-04 因诺迪亚有限公司 4-羟基异亮氨酸类似物及其用途
BRPI0611550A2 (pt) * 2005-03-22 2009-01-13 Innodia Inc uso de um composto selecionado do grupo que consiste em isâmeros de 4-hidràxi isoleucina, anÁlogos de 4-hidràxi isoleucina, e lactonas, sais, metabàlitos, solvatos e/ou prà-medicamentos farmaceuticamente aceitÁveis dos ditos isâmeros e anÁlogos, composto, kit farmacÊutico, composiÇço farmacÊutica, uso do composto e kit com composto
BRPI0608469A2 (pt) 2005-04-22 2010-01-05 Alantos Pharmaceuticals Holding Inc inibidores de dipeptidil peptidase-iv
EP1917001A2 (en) * 2005-08-11 2008-05-07 F.Hoffmann-La Roche Ag Pharmaceutical composition comprising a dpp-iv inhibitor
GB0526291D0 (en) 2005-12-23 2006-02-01 Prosidion Ltd Therapeutic method
WO2007107008A1 (en) * 2006-03-22 2007-09-27 Innodia Inc. Compounds and compositions for use in the prevention and treatment of disorders of fat metabolism and obesity
PE20071221A1 (es) 2006-04-11 2007-12-14 Arena Pharm Inc Agonistas del receptor gpr119 en metodos para aumentar la masa osea y para tratar la osteoporosis y otras afecciones caracterizadas por masa osea baja, y la terapia combinada relacionada a estos agonistas
US7727978B2 (en) * 2006-08-24 2010-06-01 Bristol-Myers Squibb Company Cyclic 11-beta hydroxysteroid dehydrogenase type I inhibitors
GB0713602D0 (en) * 2007-07-12 2007-08-22 Syngenta Participations Ag Chemical compounds
WO2009037719A1 (en) * 2007-09-21 2009-03-26 Lupin Limited Novel compounds as dipeptidyl peptidase iv (dpp iv) inhibitors
JP5305704B2 (ja) * 2008-03-24 2013-10-02 富士フイルム株式会社 新規化合物、光重合性組成物、カラーフィルタ用光重合性組成物、カラーフィルタ、及びその製造方法、固体撮像素子、並びに、平版印刷版原版
EP2108960A1 (en) 2008-04-07 2009-10-14 Arena Pharmaceuticals, Inc. Methods of using A G protein-coupled receptor to identify peptide YY (PYY) secretagogues and compounds useful in the treatment of conditons modulated by PYY
US8748457B2 (en) 2009-06-18 2014-06-10 Lupin Limited 2-amino-2- [8-(dimethyl carbamoyl)- 8-aza- bicyclo [3.2.1] oct-3-yl]-exo- ethanoyl derivatives as potent DPP-IV inhibitors
US8999975B2 (en) * 2011-09-19 2015-04-07 Boehringer Ingelheim International Gmbh Substituted N- [1-cyano-2- (phenyl) ethyl] -2-azabicyclo [2.2.1] heptane-3-carboxamide inhibitors of cathepsin C
NZ709260A (en) 2012-12-21 2016-07-29 Gilead Sciences Inc Polycyclic-carbamoylpyridone compounds and their pharmaceutical use
EP2970252B1 (en) 2013-03-14 2020-06-03 Boehringer Ingelheim International GmbH Substituted 2-aza-bicyclo[2.2.2]octane-3-carboxylic acid (benzyl-cyano-methyl)-amides inhibitors of cathepsin c
WO2014140075A1 (en) 2013-03-14 2014-09-18 Boehringer Ingelheim International Gmbh Substituted 2-aza-bicyclo[2.2.1]heptane-3-carboxylic acid (benzyl-cyano-methyl)-amides inhibitors of cathepsin c
NO2865735T3 (enExample) 2013-07-12 2018-07-21
ES2859102T3 (es) 2013-07-12 2021-10-01 Gilead Sciences Inc Compuestos de carbamoilpiridona policíclica y su uso para el tratamiento de infecciones por VIH
TWI677489B (zh) 2014-06-20 2019-11-21 美商基利科學股份有限公司 多環型胺甲醯基吡啶酮化合物之合成
NO2717902T3 (enExample) 2014-06-20 2018-06-23
TW201613936A (en) 2014-06-20 2016-04-16 Gilead Sciences Inc Crystalline forms of(2R,5S,13aR)-8-hydroxy-7,9-dioxo-n-(2,4,6-trifluorobenzyl)-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxamide
JP6529575B2 (ja) 2014-08-01 2019-06-12 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング 置換オキセタンおよびそれらのカテプシンcの阻害薬としての使用
CN108047240B (zh) 2014-09-12 2020-08-04 勃林格殷格翰国际有限公司 组织蛋白酶c的螺环化合物抑制剂
TWI695003B (zh) 2014-12-23 2020-06-01 美商基利科學股份有限公司 多環胺甲醯基吡啶酮化合物及其醫藥用途
WO2016144862A1 (en) 2015-03-09 2016-09-15 Intekrin Therapeutics, Inc. Methods for the treatment of nonalcoholic fatty liver disease and/or lipodystrophy
SI3466490T1 (sl) 2015-04-02 2020-12-31 Gilead Sciences, Inc. Policiklične spojine karbamoilpiridona in njihova farmacevtska uporaba
KR20200036808A (ko) 2017-04-03 2020-04-07 코히러스 바이오사이언시스, 인크. 진행성 핵상 마비 치료를 위한 PPARγ 작용제
IT201700059292A1 (it) * 2017-05-31 2018-12-01 Univ Pisa Derivati 1,3-diaza-4-ossa-[3.3.1]-biciclici, loro preparazione e uso come medicinale, in particolare per il trattamento del diabete
JP7352551B2 (ja) 2018-08-08 2023-09-28 住友ファーマ株式会社 光学活性な架橋型ピペリジン誘導体
WO2020045334A1 (ja) 2018-08-27 2020-03-05 大日本住友製薬株式会社 光学活性なアザビシクロ環誘導体

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TW200401635A (en) * 2002-07-23 2004-02-01 Yamanouchi Pharma Co Ltd 2-Cyano-4-fluoropyrrolidine derivative or salt thereof

Also Published As

Publication number Publication date
EP1737863A2 (en) 2007-01-03
MXPA06004797A (es) 2006-07-03
EP1737863B1 (en) 2008-12-31
BRPI0415587A (pt) 2007-01-02
AR046313A1 (es) 2005-11-30
WO2005042533A3 (en) 2005-09-01
US20050137224A1 (en) 2005-06-23
RU2006118789A (ru) 2007-12-10
TW200528440A (en) 2005-09-01
WO2005042533A2 (en) 2005-05-12
CA2543533A1 (en) 2005-05-12
ES2320557T3 (es) 2009-05-25
IL175214A0 (en) 2006-09-05
NO20062517L (no) 2006-07-21
KR20060100390A (ko) 2006-09-20
CO5690603A2 (es) 2006-10-31
US7186731B2 (en) 2007-03-06
JP2007510619A (ja) 2007-04-26
JP4636021B2 (ja) 2011-02-23
DE602004018837D1 (de) 2009-02-12

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