CA2693537C - Macrocyclic indole derivatives for the treatment of hepatitis c infections - Google Patents
Macrocyclic indole derivatives for the treatment of hepatitis c infections Download PDFInfo
- Publication number
- CA2693537C CA2693537C CA2693537A CA2693537A CA2693537C CA 2693537 C CA2693537 C CA 2693537C CA 2693537 A CA2693537 A CA 2693537A CA 2693537 A CA2693537 A CA 2693537A CA 2693537 C CA2693537 C CA 2693537C
- Authority
- CA
- Canada
- Prior art keywords
- dihydro
- indolo
- dioxide
- cyclohexyl
- benzoxazocin
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Fee Related
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/08—Bridged systems
-
- 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
- A61K31/40—Heterocyclic 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
- A61K31/407—Heterocyclic 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 condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
-
- 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
- A61K31/415—1,2-Diazoles
- A61K31/4155—1,2-Diazoles non condensed and containing further heterocyclic 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
- A61K31/435—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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4995—Pyrazines or piperazines forming part of bridged ring systems
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
- A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
- A61K31/5517—1,4-Benzodiazepines, e.g. diazepam or clozapine condensed with five-membered rings having nitrogen as a ring hetero atom, e.g. imidazobenzodiazepines, triazolam
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
- C07D513/18—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D515/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D515/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
- C07D515/18—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D515/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D515/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains four or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0713865.4 | 2007-07-17 | ||
| GB0713865A GB0713865D0 (en) | 2007-07-17 | 2007-07-17 | Therapeutic compounds |
| US823107P | 2007-12-19 | 2007-12-19 | |
| GB0724635A GB0724635D0 (en) | 2007-12-19 | 2007-12-19 | Therapeutic compounds |
| US61/008,231 | 2007-12-19 | ||
| GB0724635.8 | 2007-12-19 | ||
| PCT/GB2008/050555 WO2009010785A1 (en) | 2007-07-17 | 2008-07-09 | Macrocyclic indole derivatives for the treatment of hepatitis c infections |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2693537A1 CA2693537A1 (en) | 2009-01-22 |
| CA2693537C true CA2693537C (en) | 2013-06-25 |
Family
ID=39791042
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2693537A Expired - Fee Related CA2693537C (en) | 2007-07-17 | 2008-07-09 | Macrocyclic indole derivatives for the treatment of hepatitis c infections |
| CA2693533A Abandoned CA2693533A1 (en) | 2007-07-17 | 2008-07-09 | Macrocyclic indole derivatives for the treatment of hepatitis c infections |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2693533A Abandoned CA2693533A1 (en) | 2007-07-17 | 2008-07-09 | Macrocyclic indole derivatives for the treatment of hepatitis c infections |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7989438B2 (enExample) |
| EP (2) | EP2178885A1 (enExample) |
| JP (2) | JP2010533699A (enExample) |
| CN (2) | CN101801982A (enExample) |
| AR (1) | AR067542A1 (enExample) |
| AU (2) | AU2008277442A1 (enExample) |
| CA (2) | CA2693537C (enExample) |
| CL (1) | CL2008002049A1 (enExample) |
| GB (1) | GB2451184B (enExample) |
| PE (1) | PE20090478A1 (enExample) |
| TW (1) | TW200904411A (enExample) |
| WO (2) | WO2009010785A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2008277442A1 (en) * | 2007-07-17 | 2009-01-22 | Istituto Di Ricerche Di Biologia Molecolare P. Angeletti Spa | Macrocyclic indole derivatives for the treatment of hepatitis C infections |
| WO2009018657A1 (en) | 2007-08-03 | 2009-02-12 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| EP2234977A4 (en) | 2007-12-19 | 2011-04-13 | Boehringer Ingelheim Int | VIRAL POLYMERASE INHIBITORS |
| CN101910177B (zh) | 2007-12-24 | 2013-08-28 | 泰博特克药品公司 | 作为丙型肝炎病毒抑制剂的大环吲哚 |
| TWI454476B (zh) * | 2008-07-08 | 2014-10-01 | Tibotec Pharm Ltd | 用作c型肝炎病毒抑制劑之巨環吲哚衍生物 |
| RU2518471C2 (ru) * | 2008-08-14 | 2014-06-10 | Тиботек Фармасьютикалз | Макроциклические индольные производные, применимые в качестве ингибиторов вируса гепатита с |
| US8044087B2 (en) | 2008-09-29 | 2011-10-25 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| WO2010082050A1 (en) | 2009-01-16 | 2010-07-22 | Istituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A. | Macrocyclic and 7-aminoalkyl-substituted benzoxazocines for treatment of hepatitis c infections |
| EP3009447B1 (en) | 2009-07-24 | 2018-06-06 | Dr. Reddy's Laboratories, Ltd. | Production of erythropoiesis stimulating protein using metal ions |
| US8828930B2 (en) | 2009-07-30 | 2014-09-09 | Merck Sharp & Dohme Corp. | Hepatitis C virus NS3 protease inhibitors |
| EP2585438B1 (en) | 2010-06-24 | 2014-08-20 | Janssen R&D Ireland | PREPARATION OF 13-CYCLOHEXYL-3-METHOXY-6-[METHYL-(2-{2-[METHYL-(SULPHAMOYL)-AMINO]-ETHOXY}-ETHYL)-CARBAMOYL]-7H-INDOLO-[2,1-a]-[2]-BENZAZEPINE-10-CARBOXYLIC ACID |
| WO2014121417A1 (en) | 2013-02-07 | 2014-08-14 | Merck Sharp & Dohme Corp. | Tetracyclic heterocycle compounds and methods of use thereof for the treatment of hepatitis c |
| WO2014121416A1 (en) | 2013-02-07 | 2014-08-14 | Merck Sharp & Dohme Corp. | Tetracyclic heterocycle compounds and methods of use thereof for the treatment of hepatitis c |
| WO2014121418A1 (en) | 2013-02-07 | 2014-08-14 | Merck Sharp & Dohme Corp. | Tetracyclic heterocycle compounds and methods of use thereof for the treatment of hepatitis c |
| WO2017109088A1 (en) | 2015-12-23 | 2017-06-29 | Savira Pharmaceuticals Gmbh | Pyrimidone derivatives and their use in the treatment, amelioration or prevention of a viral disease |
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| US3480613A (en) * | 1967-07-03 | 1969-11-25 | Merck & Co Inc | 2-c or 3-c-alkylribofuranosyl - 1-substituted compounds and the nucleosides thereof |
| US4182623A (en) * | 1977-07-27 | 1980-01-08 | Monsanto Company | Bicyclothiadiazinones |
| US5206382A (en) * | 1991-06-27 | 1993-04-27 | Fidia Georgetown Institute For The Neurosciences | Indole derivatives, pharmaceutical compositions and methods of treating neurological and psychiatric disorders |
| IT1278077B1 (it) | 1995-05-25 | 1997-11-17 | Angeletti P Ist Richerche Bio | Metodologia per riprodurre in vitro le attivita' di rna polimerasi rna-dipendente e di nucleotidiltransferasi terminale codificate dal |
| US6128582A (en) | 1996-04-30 | 2000-10-03 | Vertex Pharmaceuticals Incorporated | Molecules comprising an IMPDH-like binding pocket and encoded data storage medium capable of graphically displaying them |
| GB9623908D0 (en) | 1996-11-18 | 1997-01-08 | Hoffmann La Roche | Amino acid derivatives |
| GB9707659D0 (en) | 1997-04-16 | 1997-06-04 | Peptide Therapeutics Ltd | Hepatitis C NS3 Protease inhibitors |
| IL134232A0 (en) | 1997-08-11 | 2001-04-30 | Boehringer Ingelheim Ca Ltd | Hepatitis c inhibitor peptides |
| PT1012180E (pt) | 1997-08-11 | 2005-04-29 | Boehringer Ingelheim Ca Ltd | Analogos de peptidos inibidores da hepatite c |
| IT1299134B1 (it) | 1998-02-02 | 2000-02-29 | Angeletti P Ist Richerche Bio | Procedimento per la produzione di peptidi con proprieta' inibitrici della proteasi ns3 del virus hcv, peptidi cosi' ottenibili e peptidi |
| EA200700564A1 (ru) | 1998-02-25 | 2007-08-31 | Эмори Юниверсити | 2`-фторнуклеозиды |
| GB9806815D0 (en) | 1998-03-30 | 1998-05-27 | Hoffmann La Roche | Amino acid derivatives |
| AU3376699A (en) | 1998-03-31 | 1999-10-18 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases, particularly hepatitis c virus ns3 protease |
| GB9812523D0 (en) | 1998-06-10 | 1998-08-05 | Angeletti P Ist Richerche Bio | Peptide inhibitors of hepatitis c virus ns3 protease |
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| UA74546C2 (en) | 1999-04-06 | 2006-01-16 | Boehringer Ingelheim Ca Ltd | Macrocyclic peptides having activity relative to hepatitis c virus, a pharmaceutical composition and use of the pharmaceutical composition |
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-
2008
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- 2008-07-09 EP EP08776186A patent/EP2178885A1/en not_active Withdrawn
- 2008-07-09 AU AU2008277440A patent/AU2008277440A1/en not_active Abandoned
- 2008-07-09 CA CA2693537A patent/CA2693537C/en not_active Expired - Fee Related
- 2008-07-09 EP EP08776190A patent/EP2178886A1/en not_active Withdrawn
- 2008-07-09 CA CA2693533A patent/CA2693533A1/en not_active Abandoned
- 2008-07-09 JP JP2010516593A patent/JP2010533699A/ja active Pending
- 2008-07-09 WO PCT/GB2008/050555 patent/WO2009010785A1/en not_active Ceased
- 2008-07-09 CN CN200880107414A patent/CN101801982A/zh active Pending
- 2008-07-09 CN CN2008800250052A patent/CN101754970B/zh not_active Expired - Fee Related
- 2008-07-09 WO PCT/GB2008/050551 patent/WO2009010783A1/en not_active Ceased
- 2008-07-09 JP JP2010516592A patent/JP2010533698A/ja not_active Withdrawn
- 2008-07-14 PE PE2008001173A patent/PE20090478A1/es not_active Application Discontinuation
- 2008-07-14 CL CL2008002049A patent/CL2008002049A1/es unknown
- 2008-07-14 AR ARP080103028A patent/AR067542A1/es unknown
- 2008-07-14 TW TW097126688A patent/TW200904411A/zh unknown
- 2008-07-15 US US12/218,425 patent/US7989438B2/en active Active
- 2008-07-17 GB GB0813087A patent/GB2451184B/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CL2008002049A1 (es) | 2009-01-23 |
| JP2010533699A (ja) | 2010-10-28 |
| GB0813087D0 (en) | 2008-08-27 |
| EP2178885A1 (en) | 2010-04-28 |
| CA2693533A1 (en) | 2009-01-22 |
| US20090048239A1 (en) | 2009-02-19 |
| GB2451184B (en) | 2011-09-21 |
| WO2009010783A1 (en) | 2009-01-22 |
| CA2693537A1 (en) | 2009-01-22 |
| AU2008277442A1 (en) | 2009-01-22 |
| AU2008277440A1 (en) | 2009-01-22 |
| CN101754970B (zh) | 2013-07-10 |
| TW200904411A (en) | 2009-02-01 |
| JP2010533698A (ja) | 2010-10-28 |
| CN101754970A (zh) | 2010-06-23 |
| US7989438B2 (en) | 2011-08-02 |
| AR067542A1 (es) | 2009-10-14 |
| GB2451184A (en) | 2009-01-21 |
| PE20090478A1 (es) | 2009-05-24 |
| CN101801982A (zh) | 2010-08-11 |
| WO2009010785A1 (en) | 2009-01-22 |
| EP2178886A1 (en) | 2010-04-28 |
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