AU2006339348B2 - Soft protease inhibitors and pro-soft forms thereof - Google Patents

Soft protease inhibitors and pro-soft forms thereof Download PDF

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Publication number
AU2006339348B2
AU2006339348B2 AU2006339348A AU2006339348A AU2006339348B2 AU 2006339348 B2 AU2006339348 B2 AU 2006339348B2 AU 2006339348 A AU2006339348 A AU 2006339348A AU 2006339348 A AU2006339348 A AU 2006339348A AU 2006339348 B2 AU2006339348 B2 AU 2006339348B2
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AU
Australia
Prior art keywords
compound
alkyl
alkenyl
lower alkyl
group
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Ceased
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AU2006339348A
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AU2006339348A1 (en
Inventor
William W. Bachovchin
Hung-Sen Lai
Wengen Wu
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Tufts University
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Tufts University
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Ceased legal-status Critical Current
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    • 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
    • A61K31/69—Boron compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/05—Dipeptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • A61K38/22—Hormones
    • A61K38/28—Insulins
    • 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
    • A61P3/00—Drugs for disorders of the metabolism
    • 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
    • A61P3/06—Antihyperlipidemics
    • 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
    • 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
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
    • A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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
    • C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/025—Boronic and borinic acid compounds
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/99—Enzyme inactivation by chemical treatment

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Diabetes (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Zoology (AREA)
  • Endocrinology (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Immunology (AREA)
  • Genetics & Genomics (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Wood Science & Technology (AREA)
  • Microbiology (AREA)
  • Biochemistry (AREA)
  • General Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Biotechnology (AREA)
  • Biomedical Technology (AREA)
  • Emergency Medicine (AREA)
  • Child & Adolescent Psychology (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Peptides Or Proteins (AREA)
AU2006339348A 2005-12-19 2006-12-15 Soft protease inhibitors and pro-soft forms thereof Ceased AU2006339348B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US75201705P 2005-12-19 2005-12-19
US60/752,017 2005-12-19
PCT/US2006/047853 WO2007100374A2 (en) 2005-12-19 2006-12-15 Soft protease inhibitors and pro-soft forms thereof

Publications (2)

Publication Number Publication Date
AU2006339348A1 AU2006339348A1 (en) 2007-09-07
AU2006339348B2 true AU2006339348B2 (en) 2013-01-17

Family

ID=38459469

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2006339348A Ceased AU2006339348B2 (en) 2005-12-19 2006-12-15 Soft protease inhibitors and pro-soft forms thereof

Country Status (11)

Country Link
US (5) US8268880B2 (enExample)
EP (1) EP1973548A4 (enExample)
JP (1) JP5270369B2 (enExample)
KR (2) KR20150003157A (enExample)
CN (1) CN101379069A (enExample)
AU (1) AU2006339348B2 (enExample)
BR (1) BRPI0620027A2 (enExample)
CA (1) CA2633803A1 (enExample)
IL (1) IL192134A (enExample)
NO (1) NO20083216L (enExample)
WO (1) WO2007100374A2 (enExample)

Families Citing this family (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007100374A2 (en) * 2005-12-19 2007-09-07 Trustees Of Tufts College Soft protease inhibitors and pro-soft forms thereof
JP2010523477A (ja) * 2007-03-20 2010-07-15 トラスティーズ オブ タフツ カレッジ 線維芽細胞活性化タンパク質の阻害剤、およびそれを使用する方法
EP2025674A1 (de) 2007-08-15 2009-02-18 sanofi-aventis Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
US7838673B2 (en) 2007-10-16 2010-11-23 Millennium Pharmaceuticals, Inc. Proteasome inhibitors
WO2009051581A1 (en) * 2007-10-16 2009-04-23 Millennium Pharmaceuticals, Inc. Proteasome inhibitors
EP2223115B1 (en) * 2007-12-10 2011-09-14 Roche Diagnostics GmbH Seprase as a marker for cancer
FR2942409B1 (fr) * 2009-02-20 2013-07-26 Natacha Voillot Composition pharmaceutique pour la prevention des avortements a repetition.
CA2753884A1 (en) 2009-02-27 2010-09-02 Trustees Of Tufts College Soft protease inhibitors, and pro-soft forms thereof
WO2011107494A1 (de) 2010-03-03 2011-09-09 Sanofi Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung
EP2582709B1 (de) 2010-06-18 2018-01-24 Sanofi Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen
US8530413B2 (en) 2010-06-21 2013-09-10 Sanofi Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments
TW201215388A (en) 2010-07-05 2012-04-16 Sanofi Sa (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments
TW201215387A (en) 2010-07-05 2012-04-16 Sanofi Aventis Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament
TW201221505A (en) 2010-07-05 2012-06-01 Sanofi Sa Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament
EP2766349B1 (de) 2011-03-08 2016-06-01 Sanofi Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung
EP2683704B1 (de) 2011-03-08 2014-12-17 Sanofi Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung
WO2012120054A1 (de) 2011-03-08 2012-09-13 Sanofi Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung
EP2683699B1 (de) 2011-03-08 2015-06-24 Sanofi Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung
WO2012120056A1 (de) 2011-03-08 2012-09-13 Sanofi Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung
EP4144354B1 (en) * 2011-08-30 2025-11-26 Trustees Of Tufts College Fap-activated proteasome inhibitors for treating solid tumors
WO2013037390A1 (en) 2011-09-12 2013-03-21 Sanofi 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors
WO2013045413A1 (en) 2011-09-27 2013-04-04 Sanofi 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors
AU2012340887A1 (en) 2011-11-22 2014-07-03 Trustees Of Tufts College Small molecule enhancer for dendritic cell cancer vaccines
US20150202218A1 (en) * 2012-08-02 2015-07-23 Trustees Of Tufts College Broad Spectrum Inhibitors of the Post Proline Cleaving Enzymes for Treatment of Hepatitis C Virus Infections
IN2015DN03795A (enExample) 2012-10-24 2015-10-02 Inserm Inst Nat De La Santé Et De La Rech Médicale
US10426818B2 (en) 2015-03-24 2019-10-01 Inserm (Institut National De La Sante Et De La Recherche Medicale) Method and pharmaceutical composition for use in the treatment of diabetes
WO2018049014A1 (en) * 2016-09-07 2018-03-15 Trustees Of Tufts College Dash inhibitors, and uses related thereto
ES2944544T3 (es) * 2017-02-03 2023-06-22 Univ Vanderbilt Sistemas, composiciones y métodos para el tratamiento de la diabetes
US11559537B2 (en) 2017-04-07 2023-01-24 Trustees Of Tufts College Combination therapies using caspase-1 dependent anticancer agents and PGE2 antagonists
CN108929340B (zh) * 2017-05-22 2019-12-13 北京大学 脯氨酸硼酸类化合物及其制备方法和用途
EP3704270A1 (en) * 2017-10-30 2020-09-09 Carmentix Pte. Ltd. Biomarkers of preterm birth
US20210220298A1 (en) * 2018-06-29 2021-07-22 Tufts Medical Center, Inc. Methods and compositions for preventing and treating metabolic syndrome induced by antipsychotic treatment and related diseases and conditions
EP3844171A4 (en) * 2018-08-31 2022-08-10 Texas Tech University System ENHANCER OF NEUROLYSIN ACTIVITY
CN117603084A (zh) * 2023-12-18 2024-02-27 江苏瑞思坦生物科技有限公司 肽酶神经溶素增强剂及其制备方法和应用

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993010127A1 (en) * 1991-11-22 1993-05-27 Boehringer Ingelheim Pharmaceuticals, Inc. Method for making a prolineboronate ester
US20030153509A1 (en) * 1998-02-02 2003-08-14 Bachovchin William W. Method of regulating glucose metabolism, and reagents related thereto
US6890904B1 (en) * 1999-05-25 2005-05-10 Point Therapeutics, Inc. Anti-tumor agents
WO2005082348A2 (en) * 2004-02-23 2005-09-09 Trustees Of Tufts College Inhibitors of dipeptidylpeptidase iv for regulating glucose metabolism

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03220179A (ja) * 1990-01-23 1991-09-27 Chisso Corp 新規な環状ジペプチド誘導体及びその製造法
US6825169B1 (en) * 1991-10-22 2004-11-30 Trustees Of Tufts College Inhibitors of dipeptidyl-aminopeptidase type IV
WO1995011689A1 (en) 1993-10-29 1995-05-04 Trustees Of Tufts College Use of inhibitors of dipeptidyl-aminopeptidase to block entry of hiv into cells
IL111785A0 (en) * 1993-12-03 1995-01-24 Ferring Bv Dp-iv inhibitors and pharmaceutical compositions containing them
TWI243162B (en) * 2000-11-10 2005-11-11 Taisho Pharmaceutical Co Ltd Cyanopyrrolidine derivatives
JP4771661B2 (ja) * 2001-11-26 2011-09-14 トラスティーズ オブ タフツ カレッジ Ｐｏｓｔ−プロリン開裂酵素の擬ペプチド性阻害剤
AU2002360453C1 (en) * 2001-11-26 2009-06-18 The Brigham And Women's Hospital, Inc. Methods for treating autoimmune disorders, and reagents related thereto
EP1625122A1 (en) * 2003-05-14 2006-02-15 Takeda San Diego, Inc. Dipeptidyl peptidase inhibitors
WO2007100374A2 (en) * 2005-12-19 2007-09-07 Trustees Of Tufts College Soft protease inhibitors and pro-soft forms thereof

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993010127A1 (en) * 1991-11-22 1993-05-27 Boehringer Ingelheim Pharmaceuticals, Inc. Method for making a prolineboronate ester
US20030153509A1 (en) * 1998-02-02 2003-08-14 Bachovchin William W. Method of regulating glucose metabolism, and reagents related thereto
US6890904B1 (en) * 1999-05-25 2005-05-10 Point Therapeutics, Inc. Anti-tumor agents
WO2005082348A2 (en) * 2004-02-23 2005-09-09 Trustees Of Tufts College Inhibitors of dipeptidylpeptidase iv for regulating glucose metabolism
US20050203027A1 (en) * 2004-02-23 2005-09-15 Trustees Of Tufts College Inhibitors of dipeptidylpeptidase IV

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Snow, R. J. et al (1994) J. Am. Chem. Soc., 116:10860-10869 *

Also Published As

Publication number Publication date
NO20083216L (no) 2008-09-18
JP5270369B2 (ja) 2013-08-21
WO2007100374A3 (en) 2008-11-13
US8268880B2 (en) 2012-09-18
US20160250237A1 (en) 2016-09-01
KR20080077024A (ko) 2008-08-20
US8933056B2 (en) 2015-01-13
US20090124559A1 (en) 2009-05-14
US9192646B2 (en) 2015-11-24
CN101379069A (zh) 2009-03-04
EP1973548A2 (en) 2008-10-01
BRPI0620027A2 (pt) 2011-10-25
IL192134A0 (en) 2009-08-03
IL192134A (en) 2013-04-30
KR20150003157A (ko) 2015-01-08
US20130150292A1 (en) 2013-06-13
WO2007100374A9 (en) 2007-12-06
AU2006339348A1 (en) 2007-09-07
WO2007100374A2 (en) 2007-09-07
EP1973548A4 (en) 2010-02-24
US20150157684A1 (en) 2015-06-11
US8563533B2 (en) 2013-10-22
JP2009521441A (ja) 2009-06-04
US20140128344A1 (en) 2014-05-08
CA2633803A1 (en) 2007-09-07

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