AR077301A1 - Derivados de 2-carboxamida-7-piperazinil-benzofurano como antagonistas de 5-ht1a y 5-ht1b - Google Patents
Derivados de 2-carboxamida-7-piperazinil-benzofurano como antagonistas de 5-ht1a y 5-ht1bInfo
- Publication number
- AR077301A1 AR077301A1 ARP100102339A ARP100102339A AR077301A1 AR 077301 A1 AR077301 A1 AR 077301A1 AR P100102339 A ARP100102339 A AR P100102339A AR P100102339 A ARP100102339 A AR P100102339A AR 077301 A1 AR077301 A1 AR 077301A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- heterocyclyl
- heteroaryl
- halogen
- carbocyclyl
- Prior art date
Links
- 102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 title 1
- 101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 title 1
- 102100027499 5-hydroxytryptamine receptor 1B Human genes 0.000 title 1
- 101710138639 5-hydroxytryptamine receptor 1B Proteins 0.000 title 1
- 239000005557 antagonist Substances 0.000 title 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 15
- 229910052736 halogen Inorganic materials 0.000 abstract 7
- 150000002367 halogens Chemical class 0.000 abstract 7
- 125000000623 heterocyclic group Chemical group 0.000 abstract 6
- 125000001424 substituent group Chemical group 0.000 abstract 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 4
- 125000004452 carbocyclyl group Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000004122 cyclic group Chemical group 0.000 abstract 4
- 125000001072 heteroaryl group Chemical group 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 2
- 125000005213 alkyl heteroaryl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- 239000000470 constituent Substances 0.000 abstract 2
- -1 cyano, hydroxy Chemical group 0.000 abstract 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 208000010877 cognitive disease Diseases 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
Classifications
-
- 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
-
- 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
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
- A61P25/14—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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- 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
- A61P25/28—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
-
- 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
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
- C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
- C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D307/85—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
-
- 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
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
-
- 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
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Composiciones farmacéuticas que contienen dichos compuestos y al uso de dichos compuestos en terapia, por ejemplo, en el tratamiento de trastornos cognitivos. También se proveen intermediarios utiles en su preparacion. Reivindicacion 1: Un compuesto de formula (1), donde R1 es heteroarilo o heterociclilo, donde dicho heteroarilo o heterociclilo está opcionalmente sustituido con uno o más sustituyentes seleccionados entre alquilo C1-4, halogeno, CF3, CN, alcoxi C1-4, C(O)alquilo C1-4, N(alquil C1-4)C(O)-alquilo C1-4, NHC(O)alquilo C1-4, C(O)HN(alquilo C1-4) y C(O)N(alquilo C1-4)2; R2 es alquilo C1-4, heterociclilo, alquilarilo C1-4, alquilheteroarilo C1-4, carbociclilo, alquilheterociclilo C1-4, heterociclil-heteroarilo, aril-heterociclilo, carbociclil-heteroarilo, heterociclil-arilo, donde en dichos grupos el resto heterociclilo, arilo, heteroarilo o carbociclilo puede estar opcionalmente sustituido con uno o más sustituyentes seleccionados entre halogeno, alcoxi C1-4, C(O)alquilo C1-4, alquil C0-4SO2alquilo C1-4, ciano, hidroxi y alquilo C1-4; R3 es hidrogeno o alquilo C1-4, o R2 y R3 junto con el átomo de nitrogeno pueden formar un sistema de anillo saturado que contiene 4, 5 o 6 átomos constituyentes del anillo seleccionados entre carbono y nitrogeno, y donde dicho sistema de anillo está opcionalmente sustituido con uno o más sustituyentes seleccionados entre halogeno, alquilo C1-4 y alcoxi C1-4, O-heteroarilo; R4 es hidrogeno, halogeno, metilo o metoxi, o una sal farmacéuticamente aceptable de este. Reivindicacion 39: Un compuesto de acuerdo con la formula (7) donde R2 es alquilo C1-4, heterociclilo, alquilarilo C1-4, alquilheteroarilo C1-4, carbociclilo, alquilheterociclilo C1-4, heterociclil-heteroarilo, aril-heterociclilo, carbociclil-heteroarilo, heterociclil-arilo, donde en dichos grupos el resto heterociclilo, arilo, heteroarilo o carbociclilo puede estar opcionalmente sustituido con uno o más sustituyentes seleccionados entre halogeno, alcoxi C1-4, C(O)alquilo C1-4, alquil C0-4SO2alquilo C1-4, ciano, hidroxi y alquilo C1-4; R3 es hidrogeno o alquilo C1-4, o R2 y R3 junto con el átomo de nitrogeno pueden formar un sistema de anillo saturado que contiene 4, 5 o 6 átomos constituyentes del anillo seleccionados entre carbono y nitrogeno, y donde dicho sistema de anillo está opcionalmente sustituido con uno o más sustituyentes seleccionados entre halogeno, alquilo C1-4 y alcoxi C1-4, O-heteroarilo; R4 es hidrogeno, halogeno, metilo o metoxi.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22165709P | 2009-06-30 | 2009-06-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR077301A1 true AR077301A1 (es) | 2011-08-17 |
Family
ID=43381415
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP100102339A AR077301A1 (es) | 2009-06-30 | 2010-06-30 | Derivados de 2-carboxamida-7-piperazinil-benzofurano como antagonistas de 5-ht1a y 5-ht1b |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US8367676B2 (es) |
| EP (1) | EP2448934B1 (es) |
| JP (1) | JP5767211B2 (es) |
| KR (1) | KR20120110000A (es) |
| CN (1) | CN102482264B (es) |
| AR (1) | AR077301A1 (es) |
| AU (1) | AU2010266753B2 (es) |
| BR (1) | BRPI1014222A2 (es) |
| CA (1) | CA2765475A1 (es) |
| MX (1) | MX2011013449A (es) |
| RU (1) | RU2011152516A (es) |
| TW (1) | TW201103922A (es) |
| UY (1) | UY32744A (es) |
| WO (1) | WO2011002405A1 (es) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8367676B2 (en) | 2009-06-30 | 2013-02-05 | Astrazeneca Ab | 2-carboxamide-7-piperazinyl-benzofuran derivatives 774 |
| WO2012087229A1 (en) | 2010-12-20 | 2012-06-28 | Astrazeneca Ab | 2-carboxamide-4-piperazinyl-benzofuran derivative |
| CN102993186B (zh) * | 2012-12-20 | 2015-11-18 | 北京海步国际医药科技发展有限公司 | 一种新型的哌嗪衍生物 |
| US20160002273A1 (en) * | 2013-03-07 | 2016-01-07 | Glaxosmithkline Llc | Thieno[3,2-d]pyrimidine-6-carboxamides and analogues as sirtuin modulators |
| US20210393621A1 (en) | 2018-10-26 | 2021-12-23 | The Research Foundation For The State University Of New York | Combination serotonin specific reuptake inhibitor and serotonin 1a receptor partial agonist for reducing l-dopa-induced dyskinesia |
| WO2020160151A1 (en) * | 2019-01-31 | 2020-08-06 | Kyorin Pharmaceutical Co., Ltd. | 15-pgdh inhibitors |
| WO2020183011A1 (en) | 2019-03-14 | 2020-09-17 | Institut Curie | Htr1d inhibitors and uses thereof in the treatment of cancer |
| US20230312577A1 (en) * | 2020-06-05 | 2023-10-05 | Monash University | Dual kinase-bromodomain inhibitors |
| US20230391758A1 (en) * | 2020-09-18 | 2023-12-07 | Merck Sharp & Dohme Llc | Modified benzofuran-carboxamides as glucosylceramide synthase inhibitors |
| CN117430574B (zh) * | 2023-12-20 | 2024-03-22 | 潍坊医学院 | 一种苯并呋喃衍生物及其制备方法、用途 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9125900D0 (en) * | 1991-12-05 | 1992-02-05 | Wyeth John & Brother Ltd | Piperazine derivatives |
| DK148392D0 (da) * | 1992-12-09 | 1992-12-09 | Lundbeck & Co As H | Heterocykliske forbindelser |
| EP1007523B9 (en) * | 1997-07-25 | 2004-09-08 | H. Lundbeck A/S | Indole and 2,3-dihydroindole derivatives, their preparation and use |
| AR022303A1 (es) | 1999-01-22 | 2002-09-04 | Lundbeck & Co As H | Derivados de piperidina, tetrahidropiridina y piperazina, su preparacion y utilizacion |
| MXPA03011638A (es) | 2001-06-15 | 2004-04-02 | Hoffmann La Roche | Nuevos derivados de 4-piperazinil indol con afinidad por el receptor 5-ht6. |
| US7977485B2 (en) | 2002-06-10 | 2011-07-12 | Bayer Schering Pharma Aktiengesellshaft | 2-heteroaryl carboxamides |
| GB0227240D0 (en) | 2002-11-21 | 2002-12-31 | Glaxo Group Ltd | Compounds |
| DE10259244A1 (de) * | 2002-12-17 | 2004-07-01 | Merck Patent Gmbh | N-(Indolethyl-)cycloamin-Verbindungen |
| DE10326940A1 (de) * | 2003-06-16 | 2005-01-05 | Merck Patent Gmbh | Indol-Derivate |
| DE10326939A1 (de) * | 2003-06-16 | 2005-01-05 | Merck Patent Gmbh | Indol-Derivate |
| WO2005077885A1 (en) | 2004-02-06 | 2005-08-25 | Yale University | Ruthenium-catalyzed hydroamination of olefins |
| WO2006062481A1 (en) | 2004-12-09 | 2006-06-15 | Biovitrum Ab | New benzofuran derivatives and their use in the treatment of obesity, type ii diabetes and cns disorders . |
| WO2007053093A1 (en) | 2005-11-04 | 2007-05-10 | Astrazeneca Ab | Chroman compounds as 5 ht1b antagonists |
| AR059356A1 (es) | 2006-02-14 | 2008-03-26 | Astrazeneca Ab | Nuevos radioligandos |
| EP2094686A1 (en) | 2006-09-26 | 2009-09-02 | Glaxo Group Limited | 5-{2-[4-(2-methyl-5-quinolinyl)-l-piperidinyl]ethyl} quinolinone derivatives as 5ht1a receptor modulators for treating sexual dysfunction, cognition impairement, psychotic disorders, anxiety, depression, etc. |
| CA2668959A1 (en) | 2006-11-09 | 2008-05-15 | F. Hoffmann-La Roche Ag | Indole and benzofuran 2-carboxamide derivatives |
| US8367676B2 (en) | 2009-06-30 | 2013-02-05 | Astrazeneca Ab | 2-carboxamide-7-piperazinyl-benzofuran derivatives 774 |
-
2010
- 2010-06-28 US US12/824,567 patent/US8367676B2/en not_active Expired - Fee Related
- 2010-06-29 MX MX2011013449A patent/MX2011013449A/es active IP Right Grant
- 2010-06-29 RU RU2011152516/04A patent/RU2011152516A/ru not_active Application Discontinuation
- 2010-06-29 KR KR1020117031427A patent/KR20120110000A/ko not_active Withdrawn
- 2010-06-29 CA CA2765475A patent/CA2765475A1/en not_active Abandoned
- 2010-06-29 WO PCT/SE2010/050747 patent/WO2011002405A1/en not_active Ceased
- 2010-06-29 UY UY0001032744A patent/UY32744A/es unknown
- 2010-06-29 EP EP10794458.9A patent/EP2448934B1/en active Active
- 2010-06-29 JP JP2012518512A patent/JP5767211B2/ja not_active Expired - Fee Related
- 2010-06-29 TW TW099121305A patent/TW201103922A/zh unknown
- 2010-06-29 CN CN201080038560.6A patent/CN102482264B/zh not_active Expired - Fee Related
- 2010-06-29 AU AU2010266753A patent/AU2010266753B2/en not_active Ceased
- 2010-06-29 BR BRPI1014222A patent/BRPI1014222A2/pt not_active IP Right Cessation
- 2010-06-30 AR ARP100102339A patent/AR077301A1/es unknown
-
2013
- 2013-02-04 US US13/758,098 patent/US8859534B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| KR20120110000A (ko) | 2012-10-09 |
| JP2012532125A (ja) | 2012-12-13 |
| US8859534B2 (en) | 2014-10-14 |
| TW201103922A (en) | 2011-02-01 |
| EP2448934B1 (en) | 2014-05-21 |
| WO2011002405A1 (en) | 2011-01-06 |
| CN102482264B (zh) | 2015-10-07 |
| RU2011152516A (ru) | 2013-08-10 |
| AU2010266753B2 (en) | 2013-08-08 |
| CN102482264A (zh) | 2012-05-30 |
| CA2765475A1 (en) | 2011-01-06 |
| JP5767211B2 (ja) | 2015-08-19 |
| BRPI1014222A2 (pt) | 2017-05-16 |
| UY32744A (es) | 2011-01-31 |
| MX2011013449A (es) | 2012-02-13 |
| EP2448934A1 (en) | 2012-05-09 |
| US8367676B2 (en) | 2013-02-05 |
| AU2010266753A1 (en) | 2012-01-19 |
| US20100331341A1 (en) | 2010-12-30 |
| EP2448934A4 (en) | 2012-12-05 |
| US20130296296A1 (en) | 2013-11-07 |
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