CA2801491C - C-28 amides of modified c-3 betulinic acid derivatives as hiv maturation inhibitors - Google Patents
C-28 amides of modified c-3 betulinic acid derivatives as hiv maturation inhibitors Download PDFInfo
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- CA2801491C CA2801491C CA2801491A CA2801491A CA2801491C CA 2801491 C CA2801491 C CA 2801491C CA 2801491 A CA2801491 A CA 2801491A CA 2801491 A CA2801491 A CA 2801491A CA 2801491 C CA2801491 C CA 2801491C
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- cyclopenta
- octadecahydro
- prop
- chrysen
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- 239000003112 inhibitor Substances 0.000 title abstract description 36
- QGJZLNKBHJESQX-FZFNOLFKSA-N betulinic acid Chemical class C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C QGJZLNKBHJESQX-FZFNOLFKSA-N 0.000 title abstract description 16
- 230000035800 maturation Effects 0.000 title abstract description 11
- 150000001408 amides Chemical class 0.000 title description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 256
- 208000030507 AIDS Diseases 0.000 claims abstract description 85
- 238000011282 treatment Methods 0.000 claims abstract description 21
- 239000003814 drug Substances 0.000 claims abstract description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
- 230000000840 anti-viral effect Effects 0.000 claims abstract description 11
- 241000725303 Human immunodeficiency virus Species 0.000 claims description 43
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000003085 diluting agent Substances 0.000 claims description 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- 239000003443 antiviral agent Substances 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 8
- 208000015181 infectious disease Diseases 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000002835 hiv fusion inhibitor Substances 0.000 claims description 7
- 229960005475 antiinfective agent Drugs 0.000 claims description 6
- 239000002955 immunomodulating agent Substances 0.000 claims description 6
- 229940121354 immunomodulator Drugs 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 4
- 239000004599 antimicrobial Substances 0.000 claims description 3
- 230000002584 immunomodulator Effects 0.000 claims description 3
- 229940126154 HIV entry inhibitor Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 331
- 229940079593 drug Drugs 0.000 abstract description 12
- 238000002360 preparation method Methods 0.000 description 221
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 187
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 182
- 239000000047 product Substances 0.000 description 169
- 239000007787 solid Substances 0.000 description 162
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 135
- 238000005160 1H NMR spectroscopy Methods 0.000 description 132
- 150000001412 amines Chemical class 0.000 description 118
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- 239000000543 intermediate Substances 0.000 description 102
- 230000007062 hydrolysis Effects 0.000 description 100
- 238000006460 hydrolysis reaction Methods 0.000 description 100
- 238000010640 amide synthesis reaction Methods 0.000 description 99
- 239000000203 mixture Substances 0.000 description 84
- -1 3-carboxy-3-methyl-butanoyloxy Chemical group 0.000 description 68
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 67
- 239000011541 reaction mixture Substances 0.000 description 67
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 65
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- 230000002829 reductive effect Effects 0.000 description 54
- 125000000217 alkyl group Chemical group 0.000 description 53
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- 239000000243 solution Substances 0.000 description 46
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- 239000005711 Benzoic acid Substances 0.000 description 40
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 39
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 38
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 32
- QTBSBXVTEAMEQO-GUEYOVJQSA-N acetic acid-d4 Chemical compound [2H]OC(=O)C([2H])([2H])[2H] QTBSBXVTEAMEQO-GUEYOVJQSA-N 0.000 description 32
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 31
- 125000001072 heteroaryl group Chemical group 0.000 description 30
- 229910052938 sodium sulfate Inorganic materials 0.000 description 30
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- 239000007858 starting material Substances 0.000 description 29
- 238000010511 deprotection reaction Methods 0.000 description 28
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 28
- 229910052739 hydrogen Inorganic materials 0.000 description 24
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- 125000000753 cycloalkyl group Chemical group 0.000 description 22
- 239000002904 solvent Substances 0.000 description 22
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 19
- 229910052796 boron Inorganic materials 0.000 description 19
- 239000000284 extract Substances 0.000 description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 19
- 238000006069 Suzuki reaction reaction Methods 0.000 description 18
- QTBSBXVTEAMEQO-HQMMCQRPSA-N acetic acid Chemical compound C[14C](O)=O QTBSBXVTEAMEQO-HQMMCQRPSA-N 0.000 description 18
- 239000002585 base Substances 0.000 description 17
- 239000003153 chemical reaction reagent Substances 0.000 description 17
- 238000002953 preparative HPLC Methods 0.000 description 17
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 16
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 16
- 239000012153 distilled water Substances 0.000 description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 15
- 239000000706 filtrate Substances 0.000 description 15
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 14
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 14
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- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 14
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 13
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- 239000007832 Na2SO4 Substances 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
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- 238000003818 flash chromatography Methods 0.000 description 11
- 230000003647 oxidation Effects 0.000 description 11
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 241000700605 Viruses Species 0.000 description 10
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 10
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- XPOQHMRABVBWPR-ZDUSSCGKSA-N efavirenz Chemical compound C([C@]1(C2=CC(Cl)=CC=C2NC(=O)O1)C(F)(F)F)#CC1CC1 XPOQHMRABVBWPR-ZDUSSCGKSA-N 0.000 description 10
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 10
- 238000004809 thin layer chromatography Methods 0.000 description 10
- QGJZLNKBHJESQX-UHFFFAOYSA-N 3-Epi-Betulin-Saeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C(=C)C)C5C4CCC3C21C QGJZLNKBHJESQX-UHFFFAOYSA-N 0.000 description 9
- CLOUCVRNYSHRCF-UHFFFAOYSA-N 3beta-Hydroxy-20(29)-Lupen-3,27-oic acid Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C(O)=O)CCC5(C)CCC(C(=C)C)C5C4CCC3C21C CLOUCVRNYSHRCF-UHFFFAOYSA-N 0.000 description 9
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
-
- 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
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Virology (AREA)
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- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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| PCT/US2011/038884 WO2011153319A1 (en) | 2010-06-04 | 2011-06-02 | C-28 amides of modified c-3 betulinic acid derivatives as hiv maturation inhibitors |
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| CA2801491A1 CA2801491A1 (en) | 2011-12-08 |
| CA2801491C true CA2801491C (en) | 2018-01-23 |
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| CN103339141B (zh) * | 2011-01-31 | 2016-08-24 | 百时美施贵宝公司 | 作为hiv成熟抑制剂的c-3修饰的桦木酸衍生物的c-28胺 |
| KR101886467B1 (ko) * | 2011-01-31 | 2018-08-07 | 비브 헬스케어 유케이 (넘버4) 리미티드 | Hiv 성숙 억제 활성을 갖는 c-17 및 c-3 변형 트리테르페노이드 |
| US8754069B2 (en) | 2011-09-21 | 2014-06-17 | Bristol-Myers Squibb Company | Betulinic acid derivatives with antiviral activity |
| US8906889B2 (en) | 2012-02-15 | 2014-12-09 | Bristol-Myers Squibb Company | C-3 cycloalkenyl triterpenoids with HIV maturation inhibitory activity |
| US8889854B2 (en) * | 2012-05-07 | 2014-11-18 | Bristol-Myers Squibb Company | C-17 bicyclic amines of triterpenoids with HIV maturation inhibitory activity |
| US9637516B2 (en) | 2012-12-31 | 2017-05-02 | Hetero Research Foundation | Betulinic acid proline derivatives as HIV inhibitors |
| JP6186010B2 (ja) * | 2013-02-06 | 2017-08-23 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | Ｈｉｖ成熟阻害活性を有するｃ−１９修飾トリテルペノイド類 |
| EA027861B1 (ru) * | 2013-02-25 | 2017-09-29 | Бристол-Майерс Сквибб Компани | C-3 алкил- и алкенилмодифицированные производные бетулиновой кислоты или их фармацевтические соли, противовирусная фармацевтическая композиция и фармацевтическая композиция для лечения вич на их основе |
| SMT202000581T1 (it) | 2014-04-11 | 2020-11-10 | Viiv Healthcare Uk No 4 Ltd | Triterpenoidi con attività di inibizione della maturazione di hiv, sostituiti in posizione 3 con un anello non aromatico portante un sostituente alogenoalchilico |
| US9920090B2 (en) | 2014-06-19 | 2018-03-20 | VIIV Healthcare UK (No.5) Limited | Betulinic acid derivatives with HIV maturation inhibitory activity |
| WO2015198263A2 (en) * | 2014-06-26 | 2015-12-30 | Hetero Research Foundation | Novel betulinic proline substituted derivatives as hiv inhibitors |
| US20170129916A1 (en) | 2014-06-26 | 2017-05-11 | Hetero Research Foundation | Novel betulinic proline imidazole derivatives as hiv inhibitors |
| WO2016077569A1 (en) | 2014-11-14 | 2016-05-19 | Bristol-Myers Squibb Company | C17-aryl substituted betulinic acid analogs |
| US9969767B2 (en) | 2014-11-14 | 2018-05-15 | VIIV Healthcare UK (No.5) Limited | Oxolupene derivatives |
| MA40886B1 (fr) | 2015-02-09 | 2020-03-31 | Hetero Research Foundation | Nouveau triterpénone en c-3 avec des dérivés d'amide inverse en c-28 en tant qu'inhibiteurs du vih |
| WO2016147099A2 (en) | 2015-03-16 | 2016-09-22 | Hetero Research Foundation | C-3 novel triterpenone with c-28 amide derivatives as hiv inhibitors |
| EP3328876A1 (en) | 2015-07-28 | 2018-06-06 | Glaxosmithkline Intellectual Property (No. 2) Limited | Betuin derivatives for preventing or treating hiv infections |
| CA2993758A1 (en) | 2015-07-28 | 2017-02-02 | Glaxosmithkline Intellectual Property (No.2) Limited | Betuin derivatives for preventing or treating hiv infections |
| JP2018528231A (ja) * | 2015-09-24 | 2018-09-27 | グラクソスミスクライン、インテレクチュアル、プロパティー、（ナンバー２）、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ （Ｎｏ．２） Ｌｉｍｉｔｅｄ | Ｈｉｖ成熟阻害活性を有する化合物 |
| CA3011616A1 (en) | 2016-01-20 | 2017-07-27 | Glaxosmithkline Intellectual Property (No.2) Limited | Amine derivatives of lupanes with hiv maturation inhibitory activity |
| AR107512A1 (es) | 2016-02-04 | 2018-05-09 | VIIV HEALTHCARE UK Nº 5 LTD | Triterpenoides modificados en c-3 y c-17 como inhibidores del vih-1 |
| EP3478703A1 (en) * | 2016-06-30 | 2019-05-08 | ViiV Healthcare UK (No.5) Limited | Triterpenoid inhibitors of human immunodeficiency virus replication |
| ES2970042T3 (es) | 2018-04-24 | 2024-05-24 | Viiv Healthcare Uk No 5 Ltd | Compuestos con actividad inhibidora de la maduración del VIH |
| PL237998B1 (pl) | 2018-05-28 | 2021-06-28 | Narodowy Inst Lekow | Fosfonowe pochodne kwasu 3-karboksyacylobetulinowego, sposób ich otrzymywania oraz ich zastosowanie |
| US10343997B1 (en) | 2018-12-04 | 2019-07-09 | King Saud University | Ursolic acid derivatives |
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| ATE348839T1 (de) * | 1998-03-02 | 2007-01-15 | Univ North Carolina | Acylierte betulin- und dihydrobetulinderivate, ihre herstellung und verwendung |
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| US7282521B2 (en) * | 2004-05-24 | 2007-10-16 | University Of North Carolina At Chapel Hill | Anti-retroviral moronic acid derivatives |
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-
2011
- 2011-06-02 RS RS20150587A patent/RS54239B1/sr unknown
- 2011-06-02 HU HUE11726564A patent/HUE026662T2/en unknown
- 2011-06-02 WO PCT/US2011/038884 patent/WO2011153319A1/en not_active Ceased
- 2011-06-02 US US13/151,722 patent/US8802661B2/en not_active Expired - Fee Related
- 2011-06-02 DK DK11726564.5T patent/DK2576586T3/en active
- 2011-06-02 CA CA2801491A patent/CA2801491C/en not_active Expired - Fee Related
- 2011-06-02 ES ES11726564.5T patent/ES2548905T3/es active Active
- 2011-06-02 CN CN201180035812.4A patent/CN102985438B/zh not_active Expired - Fee Related
- 2011-06-02 JP JP2013513340A patent/JP5755731B2/ja not_active Expired - Fee Related
- 2011-06-02 BR BR112012030810A patent/BR112012030810A2/pt not_active IP Right Cessation
- 2011-06-02 EP EP11726564.5A patent/EP2576586B1/en active Active
- 2011-06-02 MX MX2012013628A patent/MX2012013628A/es active IP Right Grant
- 2011-06-02 PT PT117265645T patent/PT2576586E/pt unknown
- 2011-06-02 PL PL11726564T patent/PL2576586T3/pl unknown
- 2011-06-02 HR HRP20150977TT patent/HRP20150977T1/hr unknown
- 2011-06-02 EA EA201270800A patent/EA026140B1/ru not_active IP Right Cessation
- 2011-06-02 SI SI201130604T patent/SI2576586T1/sl unknown
- 2011-06-03 AR ARP110101945A patent/AR081638A1/es not_active Application Discontinuation
- 2011-06-03 TW TW100119710A patent/TW201201792A/zh unknown
-
2015
- 2015-10-30 SM SM201500272T patent/SMT201500272B/it unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20120142653A1 (en) | 2012-06-07 |
| JP2013527243A (ja) | 2013-06-27 |
| HUE026662T2 (en) | 2016-06-28 |
| JP5755731B2 (ja) | 2015-07-29 |
| WO2011153319A1 (en) | 2011-12-08 |
| SMT201500272B (it) | 2016-01-08 |
| CA2801491A1 (en) | 2011-12-08 |
| ES2548905T3 (es) | 2015-10-21 |
| CN102985438B (zh) | 2016-05-18 |
| HRP20150977T1 (hr) | 2015-10-09 |
| PT2576586E (pt) | 2015-10-23 |
| EP2576586B1 (en) | 2015-08-12 |
| PL2576586T3 (pl) | 2016-01-29 |
| US8802661B2 (en) | 2014-08-12 |
| EA026140B1 (ru) | 2017-03-31 |
| CN102985438A (zh) | 2013-03-20 |
| EA201270800A1 (ru) | 2013-04-30 |
| DK2576586T3 (en) | 2015-11-23 |
| EP2576586A1 (en) | 2013-04-10 |
| MX2012013628A (es) | 2012-12-17 |
| SI2576586T1 (sl) | 2015-11-30 |
| TW201201792A (en) | 2012-01-16 |
| BR112012030810A2 (pt) | 2019-09-24 |
| RS54239B1 (sr) | 2015-12-31 |
| AR081638A1 (es) | 2012-10-10 |
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