AR074758A1 - Compuestos macrociclicos antivirales - Google Patents
Compuestos macrociclicos antiviralesInfo
- Publication number
- AR074758A1 AR074758A1 ARP090104923A ARP090104923A AR074758A1 AR 074758 A1 AR074758 A1 AR 074758A1 AR P090104923 A ARP090104923 A AR P090104923A AR P090104923 A ARP090104923 A AR P090104923A AR 074758 A1 AR074758 A1 AR 074758A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- alkoxy
- och2p
- aryl
- optionally substituted
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 4
- 230000000840 anti-viral effect Effects 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- 125000003118 aryl group Chemical group 0.000 abstract 7
- -1 cyano, carboxyl Chemical group 0.000 abstract 6
- 125000000623 heterocyclic group Chemical group 0.000 abstract 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 5
- 125000003545 alkoxy group Chemical group 0.000 abstract 5
- 125000005843 halogen group Chemical group 0.000 abstract 5
- 125000003342 alkenyl group Chemical group 0.000 abstract 4
- 125000000304 alkynyl group Chemical group 0.000 abstract 4
- 125000002757 morpholinyl group Chemical group 0.000 abstract 4
- 125000003386 piperidinyl group Chemical group 0.000 abstract 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 108700012707 hepatitis C virus NS3 Proteins 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 125000006684 polyhaloalkyl group Polymers 0.000 abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
- 125000001424 substituent group Chemical group 0.000 abstract 3
- 229940124530 sulfonamide Drugs 0.000 abstract 3
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000004422 alkyl sulphonamide group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000004421 aryl sulphonamide group Chemical group 0.000 abstract 2
- 125000004104 aryloxy group Chemical group 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000001188 haloalkyl group Chemical group 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004193 piperazinyl group Chemical group 0.000 abstract 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 2
- 229910052717 sulfur Inorganic materials 0.000 abstract 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 abstract 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- 150000001204 N-oxides Chemical class 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 125000005422 alkyl sulfonamido group Chemical group 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- 125000005421 aryl sulfonamido group Chemical group 0.000 abstract 1
- 125000005110 aryl thio group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 1
- 208000015181 infectious disease Diseases 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 150000002678 macrocyclic compounds Chemical class 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- 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
- C07D401/12—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 chain containing hetero atoms as chain links
-
- 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
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- 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
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
- C07K5/06165—Dipeptides with the first amino acid being heterocyclic and Pro-amino acid; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
La presente se refiere a compuestos macrocíclicos de fórmula (1) que son útiles como inhibidores de la proteasa de NS3 del virus de la hepatitis C (VHC), su síntesis y su uso para tratar o prevenir la infección por el VHC. Reivindicación 1: Un compuesto de fórmula (1) y los N-óxidos, sales y estereoisómeros de dicho compuesto, en donde cada línea de guiones (representada por l) representa un enlace doble opcional; X es N, CH, y cuando X tiene un doble enlace es C; R1 es -NH-SO2(ORf); R2 es hidrógeno, y cuando X es C o CH, R2 también puede ser alquilo C1-6; R3 es hidrógeno, alquilo C1-6, alcoxi C1-6-alquilo C1-6, cicloalquilo C3-7; R4 es arilo o Het; n es 3 4, 5 o 6; los átomos de carbono que tienen cuatro sustituyentes e incluyen al menos un enlace a un hidrógeno en un compuesto de estructura (1) pueden tener opcionalmente uno o varios de sus átomos de hidrógeno reemplazados por halo, donde el halo puede ser F, CI, Br o I, preferentemente F; R5 representa halo, alquilo C1-6, hidroxi, alcoxi C1-6, polihaloalquilo C1-6, fenilo o Het; R6 representa alcoxi C1-6, dimetilamino, o mono- o di-alquilamino C1-6; arilo, como grupo o parte de un grupo, es fenilo o naftilo opcionalmente sustituido con uno, dos o tres sustituyentes seleccionados de halo, hidroxi, nitro, ciano, carboxilo, alquilo C1-6, alcoxi C1-6, alcoxi C1-6-alquilo C1-6, alquilcarbonilo C1-6, amino, mono- o di-alquilamino C1-6, azido, mercapto, polihaloalquilo C1-6, polihaloalcoxi C1-6, cicloalquilo C3-7, pirrolidinilo, piperidinilo, piperazinilo, 4-alquil C1-6-piperazinilo, 4-alquil C1-6-carbonilpiperazinilo y morfolinilo; en donde los grupos morfolinilo y piperidinilo pueden estar opcionalmente sustituidos con uno o con dos radicales alquilo C1-6; Het, como grupo o parte de un grupo, es un anillo heterocíclico de 5 o 6 miembros saturado, parcialmente insaturado o completamente insaturado que contiene de 1 a 4 heteroátomos, cada uno independientemente seleccionado de nitrógeno, oxígeno y azufre, dicho anillo heterocíclico está opcionalmente condensado con un anillo benceno; y en donde dicho Het como un todo está opcionalmente sustituido con uno, dos o tres sustituyentes, cada uno independientemente seleccionado del grupo que consiste en halo, hidroxi, nitro, ciano, carboxilo, alquilo C1-6, alcoxi C1-6, alcoxi C1-6-alquilo C1-6, alquilcarbonilo C1-6, amino, mono- o di-alquilamino C1-6, azido, mercapto, polihaloalquilo C1-6, polihaloalcoxi C1-6, cicloalquilo C3-7, pirrolidinilo, piperidinilo, piperazinilo, 4-alquilpiperazinilo C1-6, 4-alquil C1-6-carbonilpiperazinilo y morfolinilo; en donde los grupos morfolinilo y piperidinilo pueden estar opcionalmente sustituidos con uno o con dos radicales alquilo C1-6; Rf es A3, Het1 es un grupo heterociclo o arilo, y puede estar opcionalmente sustituido con hasta dos Het y hasta cinco grupos seleccionados independientemente de R4, R5 o R6; MM es CO o un enlace; XX es O, NH, N-alquilo C1-4, un enlace o CH2; A3 se selecciona independientemente de PRT, H, -OH, -C(O)OH, ciano, alquilo, alquenilo, alquinilo, amino, amido, imido, imino, halógeno, CF3, CH2CF3, cicloalquilo, nitro, arilo, aralquilo, alcoxi, ariloxi, heterociclo, -C(A2)3, -C(A2)2-C(O)A2, -C(O)A2, -C(O)OA2, -O(A2), -N(A2)2, -S(A2), -CH2P(Y1)(A2)(OA2), -CH2P(Y1)(A2)(N(A2)2), -CH2P(Y1)(OA2)(OA2), -OCH2P(Y1)(A2)(OA2), -OCH2P(Y1)(A2)(OA2), -OCH2P(Y1)(A2)(N(A2)2), -C(O)OCH2P(Y1)(OA2)(OA2), -C(O)OCH2P(Y1)(A2)(OA2), -C(O)OCH2P(Y1)(A2)(N(A2)2), -CH2P(Y1)(OA2)(N(A2)2), -OCH2P(Y1)(OA2)(N(A2)2), -C(O)OCH2P(Y1)(OA2)(N(A2)2), -CH2P(Y1)(N(A2)2)(N(A2)2), -C(O)OCH2P(Y1)(N(A2)2)(N(A2)2), -OCH2P(Y1)(N(A2)2)(N(A2)2), -(CH2)m-heterociclo, -(CH2)mC(O)Oalquilo, -O-(CH2)m-O-C(O)-Oalquilo, -O-(CH2)-O-C(O)-(CH2)m-alquilo, -(CH2)mO-C(O)-O-alquilo, -(CH2)mO-C(O)-O-cicloalquilo, -N(H)C(Me)C(O)O-alquilo, SRr, S(O)Rr, S(O)2Rr o alcoxi arilsulfamato, en donde cada A3 puede estar opcionalmente sustituido con 1 a 4 -R111, -P(Y1)(OA2)(OA2), -P(Y1)(OA2)(N(A2)2), -P(Y1)(A2)(OA2), -P(Y1)(A2)(N(A2)2) o P(Y1)(N(A2)2)(N(A2)2, -C(=O)N(A2)2), halógeno, alquilo, alquenilo, alquinilo, arilo, carbociclo, heterociclo, aralquilo, aril-sulfonamida, aril-alquilsulfonamida, ariloxi-sulfonamida, ariloxi-alquilsulfonamida, ariloxi-arilsulfonamida, alquil-sulfonamida, alquiloxi-sulfonamida, alquiloxi-alquilsulfonamida, ariltio, -(CH2)m-heterociclo, -(CH2)m-C(O)O-alquilo, -O(CH2)mO-C(O)-O-alquilo, -O-(CH2)m-O-C(O)-(CH2)m-alquilo, -(CH2)m-O-C(O)-O-alquilo, -(CH2)m-O-C(O)-O-cicloalquilo, -N(H)C(CH3)C(O)O-alquilo, o alcoxi arilsulfonamida, opcionalmente sustituida con R111; A2 se selecciona independientemente de PRT, H, alquilo, alquenilo, alquinilo, amino, aminoácido, alcoxi, ariloxi, ciano, haloalquilo, cicloalquilo, arilo, heteroarilo, heterociclo, alquilsulfonamida o arilsulfonamida, en donde cada A2 está opcionalmente sustituido con A3; R111 se selecciona independientemente de H, alquilo, alquenilo, alquinilo, arilo, cicloalquilo, heterociclo, halógeno, haloalquilo, alquilsulfonamido, arilsulfonamido, -C(O)NHS(O)2- o -S(O)2-, opcionalmente sustituido con uno o varios A3; Y1 es independientemente O, S, N(A3), N(O)(A3), N(OA3), N(O)(OA3) o N(N(A3)(A3)); m es de 0 a 6; r es de 0 a 6.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14003008P | 2008-12-22 | 2008-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR074758A1 true AR074758A1 (es) | 2011-02-09 |
Family
ID=42026417
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP090104923A AR074758A1 (es) | 2008-12-22 | 2009-12-16 | Compuestos macrociclicos antivirales |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20100173939A1 (es) |
| EP (1) | EP2367813A1 (es) |
| JP (1) | JP2012513397A (es) |
| AR (1) | AR074758A1 (es) |
| AU (1) | AU2009330333A1 (es) |
| CA (1) | CA2746834A1 (es) |
| TW (1) | TW201036612A (es) |
| UY (1) | UY32332A (es) |
| WO (1) | WO2010075127A1 (es) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102046622A (zh) | 2008-04-15 | 2011-05-04 | 因特蒙公司 | 丙型肝炎病毒复制的新颖大环抑制剂 |
| JP2012505897A (ja) * | 2008-10-15 | 2012-03-08 | インターミューン・インコーポレーテッド | 治療用抗ウイルス性ペプチド |
| AR075584A1 (es) | 2009-02-27 | 2011-04-20 | Intermune Inc | COMPOSICIONES TERAPEUTICAS QUE COMPRENDEN beta-D-2'-DESOXI-2'-FLUORO-2'-C-METILCITIDINA Y UN DERIVADO DE ACIDO ISOINDOL CARBOXILICO Y SUS USOS. COMPUESTO. |
| NZ601629A (en) | 2010-01-27 | 2014-11-28 | Pharma Ltd Ab | Polyheterocyclic compounds highly potent as hcv inhibitors |
| US8957203B2 (en) | 2011-05-05 | 2015-02-17 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| CA2857705A1 (en) | 2011-06-16 | 2012-12-20 | AB Pharma Ltd. | Macrocyclic heterocyclic compounds for inhibiting hepatitis c virus and preparation and use thereof |
| EP2909205B1 (en) | 2012-10-19 | 2016-11-23 | Bristol-Myers Squibb Company | 9-methyl substituted hexadecahydrocyclopropa(e)pyrrolo(1,2-a)(1,4)diazacyclopentadecinyl carbamate derivatives as non-structural 3 (ns3) protease inhibitors for the treatment of hepatitis c virus infections |
| US9598433B2 (en) | 2012-11-02 | 2017-03-21 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US9643999B2 (en) | 2012-11-02 | 2017-05-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| EP2914598B1 (en) | 2012-11-02 | 2017-10-18 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| EP2914614B1 (en) | 2012-11-05 | 2017-08-16 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| EP2964664B1 (en) | 2013-03-07 | 2017-01-11 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| HRP20211456T1 (hr) | 2014-12-26 | 2021-12-24 | Emory University | Protuvirusni derivati n4-hidroksicitidina |
| ES2995458T3 (en) | 2017-12-07 | 2025-02-10 | Univ Emory | N4-hydroxycytidine derivative and anti-viral uses related thereto |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6323180B1 (en) | 1998-08-10 | 2001-11-27 | Boehringer Ingelheim (Canada) Ltd | Hepatitis C inhibitor tri-peptides |
| KR20040099425A (ko) | 2002-04-11 | 2004-11-26 | 버텍스 파마슈티칼스 인코포레이티드 | 세린 프로테아제, 특히 ｃ형 간염 바이러스 ｎｓ3-ｎｓ4프로테아제의 억제제 |
| MY140680A (en) | 2002-05-20 | 2010-01-15 | Bristol Myers Squibb Co | Hepatitis c virus inhibitors |
| ES2361011T3 (es) * | 2002-05-20 | 2011-06-13 | Bristol-Myers Squibb Company | Inhibidores del virus de la hepatitis c. |
| US7125845B2 (en) | 2003-07-03 | 2006-10-24 | Enanta Pharmaceuticals, Inc. | Aza-peptide macrocyclic hepatitis C serine protease inhibitors |
| EP1912997B1 (en) * | 2005-07-29 | 2011-09-14 | Tibotec Pharmaceuticals | Macrocyclic inhibitors of hepatitis c virus |
| PE20070211A1 (es) | 2005-07-29 | 2007-05-12 | Medivir Ab | Compuestos macrociclicos como inhibidores del virus de hepatitis c |
| US8426360B2 (en) * | 2007-11-13 | 2013-04-23 | Enanta Pharmaceuticals, Inc. | Carbocyclic oxime hepatitis C virus serine protease inhibitors |
| CA2743912A1 (en) * | 2008-11-20 | 2010-05-27 | Achillion Pharmaceuticals, Inc. | Cyclic carboxamide compounds and analogues thereof as of hepatitis c virus |
-
2009
- 2009-12-16 CA CA2746834A patent/CA2746834A1/en not_active Abandoned
- 2009-12-16 AU AU2009330333A patent/AU2009330333A1/en not_active Abandoned
- 2009-12-16 TW TW098143151A patent/TW201036612A/zh unknown
- 2009-12-16 WO PCT/US2009/068207 patent/WO2010075127A1/en active Application Filing
- 2009-12-16 UY UY0001032332A patent/UY32332A/es not_active Application Discontinuation
- 2009-12-16 AR ARP090104923A patent/AR074758A1/es unknown
- 2009-12-16 EP EP09796194A patent/EP2367813A1/en not_active Withdrawn
- 2009-12-16 JP JP2011542369A patent/JP2012513397A/ja not_active Withdrawn
- 2009-12-16 US US12/639,404 patent/US20100173939A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| UY32332A (es) | 2010-07-30 |
| AU2009330333A1 (en) | 2011-07-07 |
| CA2746834A1 (en) | 2010-07-01 |
| TW201036612A (en) | 2010-10-16 |
| JP2012513397A (ja) | 2012-06-14 |
| WO2010075127A1 (en) | 2010-07-01 |
| US20100173939A1 (en) | 2010-07-08 |
| EP2367813A1 (en) | 2011-09-28 |
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